data_structure_4a
loop_
_publ_author_name
'John Moss'
'Paul Beagley'
'Margaret A.L. Blackie'
'Kelly Chibale'
'Cailean Clarkson'
;
R.Meijboom
;
'Peter J. Smith'
'Hong Su'
_publ_section_title
;
Synthesis and Antiplasmodial Activity in vitro of
New Ferrocene-chloroquine Analogues
;
_journal_name_full               'Dalton Trans.'
_chemical_formula_sum            'C23 H26 Cl Fe N3 O'
_chemical_formula_weight         451.77
_chemical_name_common
;7-chloroquinolin-4-yl)-N'-(1'-dimethylaminomethylferrocen-1-
ylmethyl)-amine
;
_chemical_name_systematic
;
7-chloroquinolin-4-yl)-N'-(1'-dimethylaminomethylferrocen-1-ylmethyl)-amine
;
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 127.2210(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.3704(2)
_cell_length_b                   9.2289(3)
_cell_length_c                   21.7319(4)
_cell_measurement_temperature    193(2)
_cell_volume                     4211.58(16)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    PovRay
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.0\% \f scans and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            32757
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.862
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      N/A
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.243
_refine_ls_extinction_coef       0.0050(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4830
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.182
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.0727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1372
_reflns_number_gt                3594
_reflns_number_total             4830
_reflns_threshold_expression     >2sigma(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.059677(16) 0.76240(4) 0.46466(2) 0.02711(15) Uani 1 1 d . . .
Cl1 Cl 0.50242(3) 0.16788(8) 0.83661(4) 0.0455(2) Uani 1 1 d . . .
C9 C 0.31076(11) 0.3381(2) 0.63505(13) 0.0245(5) Uani 1 1 d . . .
N1 N 0.27113(10) 0.0871(2) 0.60983(12) 0.0324(5) Uani 1 1 d . . .
N3 N -0.15147(10) 0.7427(2) 0.29698(12) 0.0319(5) Uani 1 1 d . . .
C7 C 0.42213(12) 0.3791(3) 0.73959(14) 0.0321(6) Uani 1 1 d . . .
H7 H 0.4576 0.4426 0.7685 0.039 Uiso 1 1 calc R . .
N2 N 0.23982(10) 0.5335(2) 0.55513(12) 0.0292(5) Uani 1 1 d D . .
C10 C 0.17914(12) 0.6012(3) 0.49526(14) 0.0300(5) Uani 1 1 d . . .
H10A H 0.1542 0.5341 0.4508 0.036 Uiso 1 1 calc R . .
H10B H 0.1873 0.6901 0.4770 0.036 Uiso 1 1 calc R . .
C3 C 0.21544(12) 0.1402(3) 0.55112(15) 0.0337(6) Uani 1 1 d . . .
H3 H 0.1821 0.0722 0.5202 0.040 Uiso 1 1 calc R . .
C5 C 0.24845(11) 0.3903(2) 0.57189(13) 0.0252(5) Uani 1 1 d . . .
C4 C 0.20082(12) 0.2853(3) 0.53016(15) 0.0300(6) Uani 1 1 d . . .
H4 H 0.1589 0.3129 0.4879 0.036 Uiso 1 1 calc R . .
C20 C -0.03491(11) 0.7923(3) 0.37615(14) 0.0288(5) Uani 1 1 d . . .
C6 C 0.36377(12) 0.4297(3) 0.67926(14) 0.0295(5) Uani 1 1 d . . .
H6 H 0.3589 0.5299 0.6669 0.035 Uiso 1 1 calc R . .
C1 C 0.42852(12) 0.2315(3) 0.75794(14) 0.0306(6) Uani 1 1 d . . .
C2 C 0.37906(12) 0.1370(3) 0.71571(14) 0.0319(6) Uani 1 1 d . . .
H2A H 0.3852 0.0371 0.7289 0.038 Uiso 1 1 calc R . .
C15 C 0.14999(12) 0.7650(3) 0.56722(15) 0.0316(6) Uani 1 1 d . . .
H15 H 0.1814 0.8377 0.5842 0.038 Uiso 1 1 calc R . .
C13 C 0.06673(12) 0.6368(3) 0.54698(15) 0.0342(6) Uani 1 1 d . . .
H13 H 0.0323 0.6087 0.5474 0.041 Uiso 1 1 calc R . .
C11 C 0.14062(11) 0.6399(2) 0.52281(13) 0.0262(5) Uani 1 1 d . . .
C8 C 0.31857(11) 0.1877(3) 0.65219(14) 0.0269(5) Uani 1 1 d . . .
C12 C 0.08914(12) 0.5601(3) 0.51137(14) 0.0284(5) Uani 1 1 d . . .
H12 H 0.0727 0.4708 0.4845 0.034 Uiso 1 1 calc R . .
C22 C -0.17316(14) 0.8895(3) 0.29308(17) 0.0454(7) Uani 1 1 d . . .
H22A H -0.1780 0.9036 0.3340 0.068 Uiso 1 1 calc R . .
H22B H -0.2142 0.9053 0.2426 0.068 Uiso 1 1 calc R . .
H22C H -0.1419 0.9587 0.3000 0.068 Uiso 1 1 calc R . .
C21 C -0.08801(12) 0.7166(3) 0.37004(16) 0.0419(7) Uani 1 1 d . . .
H21A H -0.0795 0.6111 0.3758 0.050 Uiso 1 1 calc R . .
H21B H -0.0882 0.7485 0.4134 0.050 Uiso 1 1 calc R . .
C19 C -0.00517(14) 0.9263(3) 0.41321(16) 0.0446(7) Uani 1 1 d . . .
H19 H -0.0165 0.9886 0.4379 0.053 Uiso 1 1 calc R . .
C17 C 0.04603(13) 0.8336(4) 0.36603(17) 0.0492(8) Uani 1 1 d . . .
H17 H 0.0748 0.8215 0.3537 0.059 Uiso 1 1 calc R . .
C14 C 0.10434(13) 0.7622(3) 0.58165(15) 0.0356(6) Uani 1 1 d . . .
H14 H 0.0998 0.8327 0.6099 0.043 Uiso 1 1 calc R . .
C16 C -0.00289(13) 0.7385(3) 0.34698(15) 0.0348(6) Uani 1 1 d . . .
H16 H -0.0131 0.6509 0.3187 0.042 Uiso 1 1 calc R . .
C23 C -0.19709(14) 0.6380(4) 0.28916(18) 0.0503(8) Uani 1 1 d . . .
H23A H -0.1821 0.5393 0.2920 0.075 Uiso 1 1 calc R . .
H23B H -0.2388 0.6521 0.2393 0.075 Uiso 1 1 calc R . .
H23C H -0.2007 0.6528 0.3310 0.075 Uiso 1 1 calc R . .
C18 C 0.04485(13) 0.9500(3) 0.40655(18) 0.0512(9) Uani 1 1 d . . .
H18 H 0.0727 1.0312 0.4263 0.061 Uiso 1 1 calc R . .
O1W O 0.31914(9) 0.78486(19) 0.64863(11) 0.0361(5) Uani 1 1 d D . .
H2W H 0.3002(15) 0.8830(16) 0.634(2) 0.062(10) Uiso 1 1 d D . .
H1W H 0.335(2) 0.798(5) 0.7026(8) 0.098(14) Uiso 1 1 d D . .
H2 H 0.2724(11) 0.604(3) 0.5896(14) 0.058(10) Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Fe1 0.0194(2) 0.0238(2) 0.0275(2) 0.00390(13) 0.00857(17) 0.00240(13)
Cl1 0.0302(4) 0.0424(4) 0.0367(4) 0.0101(3) 0.0059(3) 0.0026(3)
C9 0.0242(12) 0.0256(12) 0.0237(11) -0.0002(9) 0.0145(10) 0.0021(9)
N1 0.0299(12) 0.0244(11) 0.0332(11) 0.0000(9) 0.0140(10) -0.0034(9)
N3 0.0204(11) 0.0410(13) 0.0268(11) 0.0041(9) 0.0105(9) -0.0014(9)
C7 0.0265(13) 0.0277(13) 0.0320(13) -0.0019(10) 0.0123(11) -0.0029(10)
N2 0.0245(11) 0.0263(11) 0.0317(11) 0.0024(9) 0.0142(10) 0.0047(9)
C10 0.0263(13) 0.0295(13) 0.0277(12) 0.0081(10) 0.0130(11) 0.0063(10)
C3 0.0284(13) 0.0303(13) 0.0346(14) -0.0058(11) 0.0149(12) -0.0080(11)
C5 0.0254(12) 0.0267(12) 0.0260(12) -0.0020(9) 0.0168(10) 0.0009(10)
C4 0.0229(12) 0.0336(14) 0.0278(13) 0.0004(10) 0.0124(11) 0.0010(10)
C20 0.0193(12) 0.0314(13) 0.0254(12) 0.0064(10) 0.0081(10) 0.0044(10)
C6 0.0303(13) 0.0227(13) 0.0332(13) 0.0010(10) 0.0180(12) -0.0010(10)
C1 0.0247(13) 0.0326(14) 0.0242(12) 0.0033(10) 0.0094(10) 0.0023(10)
C2 0.0320(14) 0.0249(13) 0.0307(13) 0.0040(10) 0.0146(11) 0.0005(11)
C15 0.0234(13) 0.0276(13) 0.0277(13) 0.0006(10) 0.0070(11) 0.0024(10)
C13 0.0274(13) 0.0400(15) 0.0323(13) 0.0101(11) 0.0166(12) 0.0070(11)
C11 0.0222(12) 0.0250(12) 0.0223(11) 0.0062(9) 0.0087(10) 0.0053(9)
C8 0.0272(12) 0.0235(12) 0.0273(12) -0.0013(10) 0.0151(11) -0.0003(10)
C12 0.0269(12) 0.0227(12) 0.0272(12) 0.0034(10) 0.0120(11) 0.0021(10)
C22 0.0328(15) 0.0543(19) 0.0433(16) -0.0030(14) 0.0199(14) 0.0068(14)
C21 0.0233(14) 0.0610(19) 0.0310(14) 0.0147(13) 0.0109(12) 0.0009(13)
C19 0.0357(15) 0.0305(15) 0.0363(15) 0.0025(11) 0.0054(13) 0.0138(12)
C17 0.0282(15) 0.064(2) 0.0472(17) 0.0306(16) 0.0185(14) 0.0100(14)
C14 0.0326(15) 0.0357(15) 0.0298(13) -0.0006(11) 0.0142(12) 0.0096(11)
C16 0.0308(14) 0.0404(16) 0.0262(13) 0.0069(11) 0.0136(12) 0.0053(11)
C23 0.0305(15) 0.067(2) 0.0445(17) 0.0036(15) 0.0182(14) -0.0136(14)
C18 0.0241(14) 0.0348(16) 0.0506(18) 0.0204(14) -0.0006(13) -0.0047(12)
O1W 0.0454(12) 0.0263(10) 0.0344(10) -0.0008(8) 0.0230(10) -0.0019(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 Fe1 C19 41.04(13) . . ?
C18 Fe1 C12 163.45(13) . . ?
C19 Fe1 C12 153.25(12) . . ?
C18 Fe1 C11 126.25(11) . . ?
C19 Fe1 C11 165.29(11) . . ?
C12 Fe1 C11 40.94(10) . . ?
C18 Fe1 C13 155.05(14) . . ?
C19 Fe1 C13 120.23(12) . . ?
C12 Fe1 C13 40.55(10) . . ?
C11 Fe1 C13 68.69(10) . . ?
C18 Fe1 C20 68.60(10) . . ?
C19 Fe1 C20 40.83(11) . . ?
C12 Fe1 C20 118.12(10) . . ?
C11 Fe1 C20 151.57(10) . . ?
C13 Fe1 C20 108.23(10) . . ?
C18 Fe1 C16 67.08(12) . . ?
C19 Fe1 C16 67.70(11) . . ?
C12 Fe1 C16 107.37(10) . . ?
C11 Fe1 C16 117.60(10) . . ?
C13 Fe1 C16 127.52(11) . . ?
C20 Fe1 C16 40.46(11) . . ?
C18 Fe1 C15 108.93(11) . . ?
C19 Fe1 C15 128.62(11) . . ?
C12 Fe1 C15 68.19(10) . . ?
C11 Fe1 C15 40.80(9) . . ?
C13 Fe1 C15 67.98(11) . . ?
C20 Fe1 C15 166.36(11) . . ?
C16 Fe1 C15 152.19(12) . . ?
C18 Fe1 C17 40.05(13) . . ?
C19 Fe1 C17 68.33(13) . . ?
C12 Fe1 C17 125.81(12) . . ?
C11 Fe1 C17 106.29(11) . . ?
C13 Fe1 C17 163.81(13) . . ?
C20 Fe1 C17 68.40(11) . . ?
C16 Fe1 C17 39.88(12) . . ?
C15 Fe1 C17 118.98(11) . . ?
C18 Fe1 C14 121.26(12) . . ?
C19 Fe1 C14 110.01(11) . . ?
C12 Fe1 C14 67.87(10) . . ?
C11 Fe1 C14 68.39(10) . . ?
C13 Fe1 C14 40.21(11) . . ?
C20 Fe1 C14 128.52(11) . . ?
C16 Fe1 C14 165.62(12) . . ?
C15 Fe1 C14 40.31(11) . . ?
C17 Fe1 C14 153.88(13) . . ?
C6 C9 C8 118.9(2) . . ?
C6 C9 C5 122.6(2) . . ?
C8 C9 C5 118.4(2) . . ?
C3 N1 C8 115.2(2) . . ?
C22 N3 C23 109.9(2) . . ?
C22 N3 C21 111.5(2) . . ?
C23 N3 C21 109.5(2) . . ?
C6 C7 C1 118.5(2) . . ?
C6 C7 H7 120.7 . . ?
C1 C7 H7 120.7 . . ?
C5 N2 C10 125.0(2) . . ?
C5 N2 H2 121.3(19) . . ?
C10 N2 H2 113(2) . . ?
N2 C10 C11 112.84(19) . . ?
N2 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N1 C3 C4 126.6(2) . . ?
N1 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
N2 C5 C4 124.2(2) . . ?
N2 C5 C9 119.4(2) . . ?
C4 C5 C9 116.3(2) . . ?
C3 C4 C5 119.4(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C16 C20 C19 106.5(2) . . ?
C16 C20 C21 125.1(2) . . ?
C19 C20 C21 128.4(3) . . ?
C16 C20 Fe1 69.89(15) . . ?
C19 C20 Fe1 69.19(14) . . ?
C21 C20 Fe1 124.26(17) . . ?
C7 C6 C9 121.9(2) . . ?
C7 C6 H6 119.0 . . ?
C9 C6 H6 119.0 . . ?
C2 C1 C7 122.0(2) . . ?
C2 C1 Cl1 119.47(19) . . ?
C7 C1 Cl1 118.6(2) . . ?
C1 C2 C8 120.0(2) . . ?
C1 C2 H2A 120.0 . . ?
C8 C2 H2A 120.0 . . ?
C14 C15 C11 108.2(2) . . ?
C14 C15 Fe1 69.94(15) . . ?
C11 C15 Fe1 69.14(13) . . ?
C14 C15 H15 125.9 . . ?
C11 C15 H15 125.9 . . ?
Fe1 C15 H15 126.6 . . ?
C14 C13 C12 108.2(2) . . ?
C14 C13 Fe1 70.38(15) . . ?
C12 C13 Fe1 69.64(14) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
Fe1 C13 H13 125.6 . . ?
C15 C11 C12 107.0(2) . . ?
C15 C11 C10 125.4(2) . . ?
C12 C11 C10 127.5(2) . . ?
C15 C11 Fe1 70.07(14) . . ?
C12 C11 Fe1 69.51(13) . . ?
C10 C11 Fe1 126.24(16) . . ?
N1 C8 C2 117.6(2) . . ?
N1 C8 C9 123.9(2) . . ?
C2 C8 C9 118.5(2) . . ?
C13 C12 C11 108.3(2) . . ?
C13 C12 Fe1 69.81(14) . . ?
C11 C12 Fe1 69.54(13) . . ?
C13 C12 H12 125.8 . . ?
C11 C12 H12 125.8 . . ?
Fe1 C12 H12 126.4 . . ?
N3 C22 H22A 109.5 . . ?
N3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C21 C20 114.3(2) . . ?
N3 C21 H21A 108.7 . . ?
C20 C21 H21A 108.7 . . ?
N3 C21 H21B 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C20 C19 C18 107.6(3) . . ?
C20 C19 Fe1 69.99(14) . . ?
C18 C19 Fe1 69.47(16) . . ?
C20 C19 H19 126.2 . . ?
C18 C19 H19 126.2 . . ?
Fe1 C19 H19 125.9 . . ?
C16 C17 C18 107.4(3) . . ?
C16 C17 Fe1 69.91(16) . . ?
C18 C17 Fe1 69.28(17) . . ?
C16 C17 H17 126.3 . . ?
C18 C17 H17 126.3 . . ?
Fe1 C17 H17 126.1 . . ?
C13 C14 C15 108.3(2) . . ?
C13 C14 Fe1 69.40(14) . . ?
C15 C14 Fe1 69.75(15) . . ?
C13 C14 H14 125.8 . . ?
C15 C14 H14 125.8 . . ?
Fe1 C14 H14 126.6 . . ?
C17 C16 C20 109.9(3) . . ?
C17 C16 Fe1 70.21(17) . . ?
C20 C16 Fe1 69.65(15) . . ?
C17 C16 H16 125.1 . . ?
C20 C16 H16 125.1 . . ?
Fe1 C16 H16 126.7 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C18 C19 108.6(3) . . ?
C17 C18 Fe1 70.67(16) . . ?
C19 C18 Fe1 69.49(15) . . ?
C17 C18 H18 125.7 . . ?
C19 C18 H18 125.7 . . ?
Fe1 C18 H18 125.7 . . ?
H2W O1W H1W 92(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C18 2.037(3) . ?
Fe1 C19 2.037(3) . ?
Fe1 C12 2.041(2) . ?
Fe1 C11 2.042(2) . ?
Fe1 C13 2.043(3) . ?
Fe1 C20 2.048(2) . ?
Fe1 C16 2.051(3) . ?
Fe1 C15 2.054(3) . ?
Fe1 C17 2.055(3) . ?
Fe1 C14 2.056(3) . ?
Cl1 C1 1.742(3) . ?
C9 C6 1.403(3) . ?
C9 C8 1.420(4) . ?
C9 C5 1.445(3) . ?
N1 C3 1.326(3) . ?
N1 C8 1.371(3) . ?
N3 C22 1.453(4) . ?
N3 C23 1.471(3) . ?
N3 C21 1.472(3) . ?
C7 C6 1.365(3) . ?
C7 C1 1.400(3) . ?
C7 H7 0.9500 . ?
N2 C5 1.353(3) . ?
N2 C10 1.458(3) . ?
N2 H2 0.970(2) . ?
C10 C11 1.501(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C3 C4 1.392(4) . ?
C3 H3 0.9500 . ?
C5 C4 1.400(3) . ?
C4 H4 0.9500 . ?
C20 C16 1.417(4) . ?
C20 C19 1.425(4) . ?
C20 C21 1.497(4) . ?
C6 H6 0.9500 . ?
C1 C2 1.362(4) . ?
C2 C8 1.416(3) . ?
C2 H2A 0.9500 . ?
C15 C14 1.416(4) . ?
C15 C11 1.428(3) . ?
C15 H15 0.9500 . ?
C13 C14 1.409(4) . ?
C13 C12 1.415(4) . ?
C13 H13 0.9500 . ?
C11 C12 1.428(3) . ?
C12 H12 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C19 C18 1.428(5) . ?
C19 H19 0.9500 . ?
C17 C16 1.400(4) . ?
C17 C18 1.401(5) . ?
C17 H17 0.9500 . ?
C14 H14 0.9500 . ?
C16 H16 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C18 H18 0.9500 . ?
O1W H2W 0.989(2) . ?
O1W H1W 0.989(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1W 0.970(2) 2.012(9) 2.957(3) 164(3) .
O1W H1W N3 0.989(2) 1.891(17) 2.835(3) 159(4) 8_566
O1W H2W N1 0.989(2) 1.981(5) 2.967(3) 174(3) 1_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N2 C10 C11 85.9(3) . . . . ?
C8 N1 C3 C4 -1.4(4) . . . . ?
C10 N2 C5 C4 4.7(4) . . . . ?
C10 N2 C5 C9 -177.4(2) . . . . ?
C6 C9 C5 N2 -1.5(3) . . . . ?
C8 C9 C5 N2 179.3(2) . . . . ?
C6 C9 C5 C4 176.6(2) . . . . ?
C8 C9 C5 C4 -2.6(3) . . . . ?
N1 C3 C4 C5 2.1(4) . . . . ?
N2 C5 C4 C3 178.1(2) . . . . ?
C9 C5 C4 C3 0.1(3) . . . . ?
C18 Fe1 C20 C16 79.33(19) . . . . ?
C19 Fe1 C20 C16 117.6(2) . . . . ?
C12 Fe1 C20 C16 -83.99(17) . . . . ?
C11 Fe1 C20 C16 -48.3(3) . . . . ?
C13 Fe1 C20 C16 -127.01(16) . . . . ?
C15 Fe1 C20 C16 161.4(4) . . . . ?
C17 Fe1 C20 C16 36.14(17) . . . . ?
C14 Fe1 C20 C16 -167.06(16) . . . . ?
C18 Fe1 C20 C19 -38.2(2) . . . . ?
C12 Fe1 C20 C19 158.46(17) . . . . ?
C11 Fe1 C20 C19 -165.8(2) . . . . ?
C13 Fe1 C20 C19 115.44(18) . . . . ?
C16 Fe1 C20 C19 -117.6(2) . . . . ?
C15 Fe1 C20 C19 43.9(5) . . . . ?
C17 Fe1 C20 C19 -81.4(2) . . . . ?
C14 Fe1 C20 C19 75.4(2) . . . . ?
C18 Fe1 C20 C21 -161.2(3) . . . . ?
C19 Fe1 C20 C21 -123.0(3) . . . . ?
C12 Fe1 C20 C21 35.5(3) . . . . ?
C11 Fe1 C20 C21 71.2(3) . . . . ?
C13 Fe1 C20 C21 -7.6(3) . . . . ?
C16 Fe1 C20 C21 119.4(3) . . . . ?
C15 Fe1 C20 C21 -79.1(5) . . . . ?
C17 Fe1 C20 C21 155.6(3) . . . . ?
C14 Fe1 C20 C21 -47.6(3) . . . . ?
C1 C7 C6 C9 -0.8(4) . . . . ?
C8 C9 C6 C7 -1.9(4) . . . . ?
C5 C9 C6 C7 178.9(2) . . . . ?
C6 C7 C1 C2 2.5(4) . . . . ?
C6 C7 C1 Cl1 -178.2(2) . . . . ?
C7 C1 C2 C8 -1.5(4) . . . . ?
Cl1 C1 C2 C8 179.3(2) . . . . ?
C18 Fe1 C15 C14 116.35(18) . . . . ?
C19 Fe1 C15 C14 74.6(2) . . . . ?
C12 Fe1 C15 C14 -81.05(16) . . . . ?
C11 Fe1 C15 C14 -119.6(2) . . . . ?
C13 Fe1 C15 C14 -37.19(15) . . . . ?
C20 Fe1 C15 C14 39.2(5) . . . . ?
C16 Fe1 C15 C14 -167.1(2) . . . . ?
C17 Fe1 C15 C14 159.03(17) . . . . ?
C18 Fe1 C15 C11 -124.01(17) . . . . ?
C19 Fe1 C15 C11 -165.71(16) . . . . ?
C12 Fe1 C15 C11 38.59(15) . . . . ?
C13 Fe1 C15 C11 82.45(16) . . . . ?
C20 Fe1 C15 C11 158.8(4) . . . . ?
C16 Fe1 C15 C11 -47.4(3) . . . . ?
C17 Fe1 C15 C11 -81.32(19) . . . . ?
C14 Fe1 C15 C11 119.6(2) . . . . ?
C18 Fe1 C13 C14 -50.5(3) . . . . ?
C19 Fe1 C13 C14 -85.65(18) . . . . ?
C12 Fe1 C13 C14 119.0(2) . . . . ?
C11 Fe1 C13 C14 81.32(17) . . . . ?
C20 Fe1 C13 C14 -128.76(16) . . . . ?
C16 Fe1 C13 C14 -169.55(16) . . . . ?
C15 Fe1 C13 C14 37.28(15) . . . . ?
C17 Fe1 C13 C14 156.1(4) . . . . ?
C18 Fe1 C13 C12 -169.5(2) . . . . ?
C19 Fe1 C13 C12 155.33(15) . . . . ?
C11 Fe1 C13 C12 -37.69(14) . . . . ?
C20 Fe1 C13 C12 112.23(15) . . . . ?
C16 Fe1 C13 C12 71.43(19) . . . . ?
C15 Fe1 C13 C12 -81.74(16) . . . . ?
C17 Fe1 C13 C12 37.0(4) . . . . ?
C14 Fe1 C13 C12 -119.0(2) . . . . ?
C14 C15 C11 C12 -0.7(3) . . . . ?
Fe1 C15 C11 C12 -59.98(16) . . . . ?
C14 C15 C11 C10 -179.9(2) . . . . ?
Fe1 C15 C11 C10 120.9(2) . . . . ?
C14 C15 C11 Fe1 59.23(17) . . . . ?
N2 C10 C11 C15 80.1(3) . . . . ?
N2 C10 C11 C12 -98.8(3) . . . . ?
N2 C10 C11 Fe1 170.24(16) . . . . ?
C18 Fe1 C11 C15 76.5(2) . . . . ?
C19 Fe1 C11 C15 49.4(5) . . . . ?
C12 Fe1 C11 C15 -117.9(2) . . . . ?
C13 Fe1 C11 C15 -80.56(17) . . . . ?
C20 Fe1 C11 C15 -169.69(19) . . . . ?
C16 Fe1 C11 C15 157.18(16) . . . . ?
C17 Fe1 C11 C15 115.72(17) . . . . ?
C14 Fe1 C11 C15 -37.21(16) . . . . ?
C18 Fe1 C11 C12 -165.62(17) . . . . ?
C19 Fe1 C11 C12 167.3(4) . . . . ?
C13 Fe1 C11 C12 37.34(15) . . . . ?
C20 Fe1 C11 C12 -51.8(3) . . . . ?
C16 Fe1 C11 C12 -84.92(17) . . . . ?
C15 Fe1 C11 C12 117.9(2) . . . . ?
C17 Fe1 C11 C12 -126.39(16) . . . . ?
C14 Fe1 C11 C12 80.69(16) . . . . ?
C18 Fe1 C11 C10 -43.4(3) . . . . ?
C19 Fe1 C11 C10 -70.5(5) . . . . ?
C12 Fe1 C11 C10 122.2(3) . . . . ?
C13 Fe1 C11 C10 159.5(2) . . . . ?
C20 Fe1 C11 C10 70.4(3) . . . . ?
C16 Fe1 C11 C10 37.3(2) . . . . ?
C15 Fe1 C11 C10 -119.9(3) . . . . ?
C17 Fe1 C11 C10 -4.2(2) . . . . ?
C14 Fe1 C11 C10 -157.1(2) . . . . ?
C3 N1 C8 C2 179.9(2) . . . . ?
C3 N1 C8 C9 -1.4(4) . . . . ?
C1 C2 C8 N1 177.5(2) . . . . ?
C1 C2 C8 C9 -1.3(4) . . . . ?
C6 C9 C8 N1 -175.8(2) . . . . ?
C5 C9 C8 N1 3.5(3) . . . . ?
C6 C9 C8 C2 2.9(3) . . . . ?
C5 C9 C8 C2 -177.9(2) . . . . ?
C14 C13 C12 C11 -1.0(3) . . . . ?
Fe1 C13 C12 C11 59.08(16) . . . . ?
C14 C13 C12 Fe1 -60.10(17) . . . . ?
C15 C11 C12 C13 1.1(3) . . . . ?
C10 C11 C12 C13 -179.8(2) . . . . ?
Fe1 C11 C12 C13 -59.24(16) . . . . ?
C15 C11 C12 Fe1 60.33(16) . . . . ?
C10 C11 C12 Fe1 -120.6(2) . . . . ?
C18 Fe1 C12 C13 164.3(4) . . . . ?
C19 Fe1 C12 C13 -53.2(3) . . . . ?
C11 Fe1 C12 C13 119.6(2) . . . . ?
C20 Fe1 C12 C13 -85.47(17) . . . . ?
C16 Fe1 C12 C13 -128.02(16) . . . . ?
C15 Fe1 C12 C13 81.17(16) . . . . ?
C17 Fe1 C12 C13 -168.05(16) . . . . ?
C14 Fe1 C12 C13 37.55(16) . . . . ?
C18 Fe1 C12 C11 44.7(4) . . . . ?
C19 Fe1 C12 C11 -172.9(2) . . . . ?
C13 Fe1 C12 C11 -119.6(2) . . . . ?
C20 Fe1 C12 C11 154.90(14) . . . . ?
C16 Fe1 C12 C11 112.35(15) . . . . ?
C15 Fe1 C12 C11 -38.46(15) . . . . ?
C17 Fe1 C12 C11 72.32(18) . . . . ?
C14 Fe1 C12 C11 -82.08(16) . . . . ?
C22 N3 C21 C20 -71.7(3) . . . . ?
C23 N3 C21 C20 166.5(3) . . . . ?
C16 C20 C21 N3 -85.0(3) . . . . ?
C19 C20 C21 N3 97.2(3) . . . . ?
Fe1 C20 C21 N3 -173.28(19) . . . . ?
C16 C20 C19 C18 -0.7(3) . . . . ?
C21 C20 C19 C18 177.4(2) . . . . ?
Fe1 C20 C19 C18 59.54(18) . . . . ?
C16 C20 C19 Fe1 -60.25(17) . . . . ?
C21 C20 C19 Fe1 117.8(3) . . . . ?
C18 Fe1 C19 C20 118.7(3) . . . . ?
C12 Fe1 C19 C20 -46.0(3) . . . . ?
C11 Fe1 C19 C20 152.7(4) . . . . ?
C13 Fe1 C19 C20 -83.07(18) . . . . ?
C16 Fe1 C19 C20 38.45(16) . . . . ?
C15 Fe1 C19 C20 -167.92(15) . . . . ?
C17 Fe1 C19 C20 81.61(18) . . . . ?
C14 Fe1 C19 C20 -126.32(17) . . . . ?
C12 Fe1 C19 C18 -164.7(2) . . . . ?
C11 Fe1 C19 C18 34.0(5) . . . . ?
C13 Fe1 C19 C18 158.26(18) . . . . ?
C20 Fe1 C19 C18 -118.7(3) . . . . ?
C16 Fe1 C19 C18 -80.2(2) . . . . ?
C15 Fe1 C19 C18 73.4(2) . . . . ?
C17 Fe1 C19 C18 -37.06(18) . . . . ?
C14 Fe1 C19 C18 115.02(19) . . . . ?
C18 Fe1 C17 C16 -118.7(2) . . . . ?
C19 Fe1 C17 C16 -80.72(18) . . . . ?
C12 Fe1 C17 C16 73.2(2) . . . . ?
C11 Fe1 C17 C16 113.77(17) . . . . ?
C13 Fe1 C17 C16 44.3(5) . . . . ?
C20 Fe1 C17 C16 -36.65(16) . . . . ?
C15 Fe1 C17 C16 156.06(16) . . . . ?
C14 Fe1 C17 C16 -172.2(2) . . . . ?
C19 Fe1 C17 C18 37.94(17) . . . . ?
C12 Fe1 C17 C18 -168.14(16) . . . . ?
C11 Fe1 C17 C18 -127.56(17) . . . . ?
C13 Fe1 C17 C18 163.0(3) . . . . ?
C20 Fe1 C17 C18 82.02(18) . . . . ?
C16 Fe1 C17 C18 118.7(2) . . . . ?
C15 Fe1 C17 C18 -85.27(19) . . . . ?
C14 Fe1 C17 C18 -53.5(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?
Fe1 C13 C14 C15 -59.08(18) . . . . ?
C12 C13 C14 Fe1 59.63(17) . . . . ?
C11 C15 C14 C13 0.1(3) . . . . ?
Fe1 C15 C14 C13 58.86(18) . . . . ?
C11 C15 C14 Fe1 -58.73(17) . . . . ?
C18 Fe1 C14 C13 157.64(17) . . . . ?
C19 Fe1 C14 C13 113.52(17) . . . . ?
C12 Fe1 C14 C13 -37.86(15) . . . . ?
C11 Fe1 C14 C13 -82.13(16) . . . . ?
C20 Fe1 C14 C13 71.20(19) . . . . ?
C16 Fe1 C14 C13 35.4(5) . . . . ?
C15 Fe1 C14 C13 -119.8(2) . . . . ?
C17 Fe1 C14 C13 -165.1(2) . . . . ?
C18 Fe1 C14 C15 -82.59(18) . . . . ?
C19 Fe1 C14 C15 -126.70(16) . . . . ?
C12 Fe1 C14 C15 81.92(15) . . . . ?
C11 Fe1 C14 C15 37.65(14) . . . . ?
C13 Fe1 C14 C15 119.8(2) . . . . ?
C20 Fe1 C14 C15 -169.02(15) . . . . ?
C16 Fe1 C14 C15 155.2(4) . . . . ?
C17 Fe1 C14 C15 -45.3(3) . . . . ?
C18 C17 C16 C20 -0.9(3) . . . . ?
Fe1 C17 C16 C20 58.47(18) . . . . ?
C18 C17 C16 Fe1 -59.34(19) . . . . ?
C19 C20 C16 C17 1.0(3) . . . . ?
C21 C20 C16 C17 -177.2(2) . . . . ?
Fe1 C20 C16 C17 -58.82(19) . . . . ?
C19 C20 C16 Fe1 59.80(17) . . . . ?
C21 C20 C16 Fe1 -118.4(2) . . . . ?
C18 Fe1 C16 C17 37.80(19) . . . . ?
C19 Fe1 C16 C17 82.4(2) . . . . ?
C12 Fe1 C16 C17 -125.57(18) . . . . ?
C11 Fe1 C16 C17 -82.41(19) . . . . ?
C13 Fe1 C16 C17 -165.78(18) . . . . ?
C20 Fe1 C16 C17 121.2(2) . . . . ?
C15 Fe1 C16 C17 -49.5(3) . . . . ?
C14 Fe1 C16 C17 166.1(4) . . . . ?
C18 Fe1 C16 C20 -83.42(18) . . . . ?
C19 Fe1 C16 C20 -38.79(16) . . . . ?
C12 Fe1 C16 C20 113.21(15) . . . . ?
C11 Fe1 C16 C20 156.36(14) . . . . ?
C13 Fe1 C16 C20 72.99(18) . . . . ?
C15 Fe1 C16 C20 -170.7(2) . . . . ?
C17 Fe1 C16 C20 -121.2(2) . . . . ?
C14 Fe1 C16 C20 44.9(5) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
Fe1 C17 C18 C19 -59.34(19) . . . . ?
C16 C17 C18 Fe1 59.74(18) . . . . ?
C20 C19 C18 C17 0.2(3) . . . . ?
Fe1 C19 C18 C17 60.07(19) . . . . ?
C20 C19 C18 Fe1 -59.87(18) . . . . ?
C19 Fe1 C18 C17 -119.5(2) . . . . ?
C12 Fe1 C18 C17 35.8(4) . . . . ?
C11 Fe1 C18 C17 70.64(19) . . . . ?
C13 Fe1 C18 C17 -168.8(2) . . . . ?
C20 Fe1 C18 C17 -81.47(17) . . . . ?
C16 Fe1 C18 C17 -37.65(17) . . . . ?
C15 Fe1 C18 C17 112.83(17) . . . . ?
C14 Fe1 C18 C17 155.53(17) . . . . ?
C12 Fe1 C18 C19 155.3(3) . . . . ?
C11 Fe1 C18 C19 -169.86(15) . . . . ?
C13 Fe1 C18 C19 -49.3(3) . . . . ?
C20 Fe1 C18 C19 38.03(17) . . . . ?
C16 Fe1 C18 C19 81.86(18) . . . . ?
C15 Fe1 C18 C19 -127.66(17) . . . . ?
C17 Fe1 C18 C19 119.5(2) . . . . ?
C14 Fe1 C18 C19 -84.96(19) . . . . ?
data_structure_5a
loop_
_publ_author_name
'John Moss'
'Paul Beagley'
'Margaret A.L. Blackie'
'Kelly Chibale'
'Cailean Clarkson'
;
R.Meijboom
;
'Peter J. Smith'
'Hong Su'
_publ_section_title
;
Synthesis and Antiplasmodial Activity in vitro of
New Ferrocene-chloroquine Analogues
;
_journal_name_full               'Dalton Trans.'
_chemical_formula_sum            'C25 H29 Cl Fe N4'
_chemical_formula_weight         476.82
_chemical_name_common
;
N-(7-chloro-quinolin-4-yl)-N&#x0092;-(2-dimethylaminomethylferrocen-
1-ylmethyl) -ethane-1,2-diamine
;
_chemical_name_systematic
;
N-(7-chloro-quinolin-4-yl)-N&#x0092;-(2-dimethylaminomethylferrocen-1-ylmethyl)
-ethane-1,2-diamine
;
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.7270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7012(3)
_cell_length_b                   16.2573(4)
_cell_length_c                   13.7853(3)
_cell_measurement_temperature    173(2)
_cell_volume                     2395.55(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    PovRay
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.0\% \f scans and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10265
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.760
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      N/A
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0000(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5459
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.6881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                4107
_reflns_number_total             5459
_reflns_threshold_expression     >2sigma(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.15410(2) 0.203002(14) 0.455355(17) 0.02922(9) Uani 1 1 d . . .
Cl Cl 0.14234(6) 0.88336(3) 0.33769(4) 0.05484(16) Uani 1 1 d . . .
C1 C 0.15796(17) 0.32787(10) 0.44095(12) 0.0306(4) Uani 1 1 d . . .
C18 C 0.23098(16) 0.79460(10) 0.32482(13) 0.0315(4) Uani 1 1 d . . .
N1 N 0.44655(13) 0.39014(8) 0.41524(10) 0.0281(3) Uani 1 1 d D . .
C2 C 0.28110(17) 0.29648(10) 0.46135(12) 0.0290(4) Uani 1 1 d . . .
C16 C 0.36892(16) 0.69556(10) 0.39877(12) 0.0299(4) Uani 1 1 d . . .
H16 H 0.4103 0.6729 0.4551 0.036 Uiso 1 1 calc R . .
C6 C 0.1933(2) 0.13109(11) 0.33925(14) 0.0406(5) Uani 1 1 d . . .
H6 H 0.2545 0.1423 0.2933 0.049 Uiso 1 1 calc R . .
C19 C 0.24157(16) 0.75980(11) 0.23576(12) 0.0310(4) Uani 1 1 d . . .
H19 H 0.1950 0.7814 0.1811 0.037 Uiso 1 1 calc R . .
C20 C 0.32134(16) 0.69186(10) 0.22431(12) 0.0285(4) Uani 1 1 d . . .
C15 C 0.38704(15) 0.65906(10) 0.30742(11) 0.0260(4) Uani 1 1 d . . .
N3 N 0.33238(15) 0.66225(10) 0.13211(10) 0.0369(4) Uani 1 1 d . . .
C8 C 0.0980(2) 0.08402(11) 0.47411(14) 0.0430(5) Uani 1 1 d . . .
H8 H 0.0840 0.0580 0.5343 0.052 Uiso 1 1 calc R . .
C11 C 0.38964(17) 0.30798(10) 0.39883(13) 0.0320(4) Uani 1 1 d . . .
H11A H 0.4530 0.2649 0.4139 0.038 Uiso 1 1 calc R . .
H11B H 0.3614 0.3024 0.3297 0.038 Uiso 1 1 calc R . .
N2 N 0.52978(14) 0.55563(9) 0.37285(11) 0.0323(3) Uani 1 1 d D . .
C14 C 0.46872(16) 0.59003(10) 0.29461(12) 0.0290(4) Uani 1 1 d . . .
C5 C 0.0827(2) 0.30478(11) 0.51937(14) 0.0406(5) Uani 1 1 d . . .
H5 H -0.0033 0.3174 0.5250 0.049 Uiso 1 1 calc R . .
C3 C 0.2809(2) 0.25510(11) 0.55261(13) 0.0396(5) Uani 1 1 d . . .
H3 H 0.3507 0.2289 0.5846 0.047 Uiso 1 1 calc R . .
C13 C 0.61284(17) 0.48516(11) 0.36821(15) 0.0377(4) Uani 1 1 d . . .
H13A H 0.6622 0.4808 0.4306 0.045 Uiso 1 1 calc R . .
H13B H 0.6722 0.4949 0.3165 0.045 Uiso 1 1 calc R . .
C7 C 0.2128(2) 0.08646(11) 0.42695(15) 0.0454(5) Uani 1 1 d . . .
H7 H 0.2894 0.0624 0.4501 0.054 Uiso 1 1 calc R . .
C12 C 0.54614(17) 0.40369(11) 0.34830(14) 0.0367(4) Uani 1 1 d . . .
H12A H 0.5102 0.4034 0.2808 0.044 Uiso 1 1 calc R . .
H12B H 0.6074 0.3582 0.3548 0.044 Uiso 1 1 calc R . .
C22 C 0.48021(18) 0.56231(12) 0.19984(13) 0.0375(4) Uani 1 1 d . . .
H22 H 0.5347 0.5180 0.1868 0.045 Uiso 1 1 calc R . .
C21 C 0.41076(19) 0.60042(12) 0.12434(13) 0.0412(5) Uani 1 1 d . . .
H21 H 0.4211 0.5796 0.0608 0.049 Uiso 1 1 calc R . .
C17 C 0.29350(17) 0.76244(11) 0.40806(13) 0.0339(4) Uani 1 1 d . . .
H17 H 0.2835 0.7868 0.4699 0.041 Uiso 1 1 calc R . .
C10 C 0.06708(19) 0.15578(11) 0.33225(13) 0.0390(5) Uani 1 1 d . . .
H10 H 0.0281 0.1864 0.2805 0.047 Uiso 1 1 calc R . .
C4 C 0.1590(2) 0.25982(12) 0.58722(14) 0.0474(6) Uani 1 1 d . . .
H4 H 0.1326 0.2367 0.6461 0.057 Uiso 1 1 calc R . .
C9 C 0.00831(19) 0.12712(11) 0.41551(14) 0.0399(5) Uani 1 1 d . . .
H9 H -0.0768 0.1354 0.4296 0.048 Uiso 1 1 calc R . .
N4 N 0.17788(13) 0.45557(8) 0.34553(11) 0.0317(3) Uani 1 1 d . . .
C23 C 0.11812(18) 0.37443(10) 0.35082(13) 0.0356(4) Uani 1 1 d . . .
H23A H 0.1392 0.3417 0.2933 0.043 Uiso 1 1 calc R . .
H23B H 0.0262 0.3817 0.3488 0.043 Uiso 1 1 calc R . .
C25 C 0.1255(2) 0.51216(12) 0.41399(17) 0.0496(5) Uani 1 1 d . . .
H25A H 0.1697 0.5649 0.4119 0.074 Uiso 1 1 calc R . .
H25B H 0.1347 0.4891 0.4796 0.074 Uiso 1 1 calc R . .
H25C H 0.0365 0.5208 0.3967 0.074 Uiso 1 1 calc R . .
C24 C 0.1604(2) 0.48764(12) 0.24652(15) 0.0478(5) Uani 1 1 d . . .
H24A H 0.0708 0.4911 0.2288 0.072 Uiso 1 1 calc R . .
H24B H 0.2009 0.4508 0.2014 0.072 Uiso 1 1 calc R . .
H24C H 0.1978 0.5425 0.2432 0.072 Uiso 1 1 calc R . .
H2 H 0.5238(19) 0.5810(12) 0.4361(7) 0.055(6) Uiso 1 1 d D . .
H1 H 0.3790(11) 0.4284(8) 0.3998(12) 0.031(5) Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Fe 0.03855(16) 0.02108(13) 0.02813(14) -0.00060(10) 0.00276(10) -0.00442(10)
Cl 0.0646(4) 0.0514(3) 0.0475(3) -0.0026(2) -0.0075(3) 0.0264(3)
C1 0.0391(11) 0.0197(8) 0.0328(9) -0.0033(7) 0.0001(8) -0.0039(7)
C18 0.0288(10) 0.0307(9) 0.0346(9) 0.0018(8) -0.0024(7) 0.0003(7)
N1 0.0267(8) 0.0208(7) 0.0363(8) -0.0001(6) -0.0032(6) 0.0017(6)
C2 0.0379(10) 0.0207(8) 0.0277(8) -0.0017(7) -0.0052(7) -0.0048(7)
C16 0.0345(10) 0.0295(9) 0.0248(8) 0.0035(7) -0.0077(7) -0.0033(7)
C6 0.0505(13) 0.0294(9) 0.0431(11) -0.0112(9) 0.0130(9) -0.0082(9)
C19 0.0301(10) 0.0348(9) 0.0277(9) 0.0070(8) -0.0044(7) -0.0045(8)
C20 0.0304(9) 0.0312(9) 0.0239(8) 0.0022(7) 0.0000(7) -0.0101(7)
C15 0.0262(9) 0.0257(8) 0.0260(8) 0.0019(7) -0.0013(7) -0.0075(7)
N3 0.0471(10) 0.0405(9) 0.0233(7) 0.0041(7) 0.0027(7) -0.0023(8)
C8 0.0627(14) 0.0256(9) 0.0409(11) 0.0037(8) 0.0024(10) -0.0152(9)
C11 0.0337(10) 0.0260(9) 0.0358(10) -0.0029(7) -0.0043(8) -0.0017(7)
N2 0.0333(9) 0.0264(7) 0.0366(8) -0.0001(7) -0.0048(7) 0.0000(6)
C14 0.0286(10) 0.0276(9) 0.0310(9) 0.0020(7) 0.0015(7) -0.0085(7)
C5 0.0505(13) 0.0290(9) 0.0436(11) -0.0070(9) 0.0161(9) -0.0018(9)
C3 0.0575(14) 0.0285(10) 0.0316(10) 0.0009(8) -0.0094(9) -0.0075(9)
C13 0.0282(10) 0.0353(10) 0.0494(11) 0.0031(9) -0.0003(8) 0.0009(8)
C7 0.0520(14) 0.0242(9) 0.0594(13) -0.0053(9) -0.0030(11) 0.0017(9)
C12 0.0340(11) 0.0294(9) 0.0471(11) 0.0001(8) 0.0072(9) 0.0047(8)
C22 0.0384(11) 0.0360(10) 0.0390(10) -0.0007(8) 0.0097(9) -0.0012(8)
C21 0.0525(13) 0.0459(11) 0.0261(9) -0.0025(9) 0.0101(9) -0.0057(10)
C17 0.0395(11) 0.0344(10) 0.0272(9) -0.0026(8) -0.0038(8) -0.0016(8)
C10 0.0502(13) 0.0341(10) 0.0325(10) -0.0051(8) 0.0000(9) -0.0094(9)
C4 0.0811(17) 0.0338(10) 0.0280(10) -0.0018(8) 0.0091(10) -0.0082(10)
C9 0.0417(12) 0.0371(10) 0.0412(11) -0.0057(9) 0.0039(9) -0.0131(9)
N4 0.0293(8) 0.0262(7) 0.0389(8) 0.0060(6) -0.0043(7) -0.0025(6)
C23 0.0374(11) 0.0269(9) 0.0416(10) 0.0043(8) -0.0084(8) -0.0048(8)
C25 0.0459(13) 0.0325(10) 0.0707(15) -0.0045(10) 0.0067(11) 0.0006(9)
C24 0.0464(13) 0.0442(11) 0.0511(12) 0.0189(10) -0.0146(10) -0.0123(9)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 Fe C2 68.71(8) . . ?
C4 Fe C7 126.68(8) . . ?
C2 Fe C7 119.33(8) . . ?
C4 Fe C1 68.65(7) . . ?
C2 Fe C1 41.01(7) . . ?
C7 Fe C1 153.85(8) . . ?
C4 Fe C5 40.61(8) . . ?
C2 Fe C5 68.92(8) . . ?
C7 Fe C5 163.98(8) . . ?
C1 Fe C5 40.97(7) . . ?
C4 Fe C6 164.05(9) . . ?
C2 Fe C6 107.30(8) . . ?
C7 Fe C6 40.62(8) . . ?
C1 Fe C6 119.18(7) . . ?
C5 Fe C6 153.95(8) . . ?
C4 Fe C9 120.02(9) . . ?
C2 Fe C9 163.79(7) . . ?
C7 Fe C9 68.02(8) . . ?
C1 Fe C9 126.38(8) . . ?
C5 Fe C9 108.00(8) . . ?
C6 Fe C9 68.06(8) . . ?
C4 Fe C3 40.47(8) . . ?
C2 Fe C3 40.90(7) . . ?
C7 Fe C3 108.06(8) . . ?
C1 Fe C3 68.64(7) . . ?
C5 Fe C3 68.34(9) . . ?
C6 Fe C3 126.62(9) . . ?
C9 Fe C3 154.21(8) . . ?
C4 Fe C8 108.13(8) . . ?
C2 Fe C8 154.07(8) . . ?
C7 Fe C8 40.59(8) . . ?
C1 Fe C8 163.87(8) . . ?
C5 Fe C8 126.45(8) . . ?
C6 Fe C8 68.29(8) . . ?
C9 Fe C8 40.37(8) . . ?
C3 Fe C8 119.89(8) . . ?
C4 Fe C10 154.36(9) . . ?
C2 Fe C10 126.15(7) . . ?
C7 Fe C10 67.93(8) . . ?
C1 Fe C10 107.65(7) . . ?
C5 Fe C10 119.87(9) . . ?
C6 Fe C10 40.30(8) . . ?
C9 Fe C10 40.45(7) . . ?
C3 Fe C10 163.89(8) . . ?
C8 Fe C10 67.99(8) . . ?
C5 C1 C2 107.75(16) . . ?
C5 C1 C23 127.71(18) . . ?
C2 C1 C23 124.52(17) . . ?
C5 C1 Fe 69.52(10) . . ?
C2 C1 Fe 69.40(9) . . ?
C23 C1 Fe 125.22(12) . . ?
C19 C18 C17 121.76(16) . . ?
C19 C18 Cl 120.37(13) . . ?
C17 C18 Cl 117.83(14) . . ?
C12 N1 C11 110.30(13) . . ?
C3 C2 C1 107.56(17) . . ?
C3 C2 C11 127.09(17) . . ?
C1 C2 C11 125.33(15) . . ?
C3 C2 Fe 69.82(10) . . ?
C1 C2 Fe 69.59(10) . . ?
C11 C2 Fe 127.34(11) . . ?
C17 C16 C15 121.67(15) . . ?
C10 C6 C7 107.81(18) . . ?
C10 C6 Fe 70.01(11) . . ?
C7 C6 Fe 69.61(11) . . ?
C18 C19 C20 120.23(15) . . ?
N3 C20 C19 117.32(15) . . ?
N3 C20 C15 123.77(16) . . ?
C19 C20 C15 118.91(15) . . ?
C16 C15 C20 118.54(15) . . ?
C16 C15 C14 123.13(14) . . ?
C20 C15 C14 118.33(15) . . ?
C21 N3 C20 115.29(15) . . ?
C9 C8 C7 107.71(17) . . ?
C9 C8 Fe 69.74(10) . . ?
C7 C8 Fe 69.49(10) . . ?
N1 C11 C2 110.54(14) . . ?
C14 N2 C13 124.27(15) . . ?
N2 C14 C22 123.53(16) . . ?
N2 C14 C15 119.81(15) . . ?
C22 C14 C15 116.67(15) . . ?
C4 C5 C1 107.93(18) . . ?
C4 C5 Fe 69.58(11) . . ?
C1 C5 Fe 69.50(10) . . ?
C4 C3 C2 108.22(17) . . ?
C4 C3 Fe 69.48(11) . . ?
C2 C3 Fe 69.28(10) . . ?
N2 C13 C12 114.27(15) . . ?
C6 C7 C8 108.09(18) . . ?
C6 C7 Fe 69.76(10) . . ?
C8 C7 Fe 69.92(11) . . ?
N1 C12 C13 111.55(15) . . ?
C14 C22 C21 119.24(17) . . ?
N3 C21 C22 126.66(17) . . ?
C16 C17 C18 118.82(16) . . ?
C6 C10 C9 108.23(18) . . ?
C6 C10 Fe 69.69(11) . . ?
C9 C10 Fe 69.68(11) . . ?
C3 C4 C5 108.52(17) . . ?
C3 C4 Fe 70.06(11) . . ?
C5 C4 Fe 69.82(11) . . ?
C8 C9 C10 108.15(19) . . ?
C8 C9 Fe 69.88(11) . . ?
C10 C9 Fe 69.87(11) . . ?
C25 N4 C24 110.14(16) . . ?
C25 N4 C23 110.78(15) . . ?
C24 N4 C23 109.22(14) . . ?
N4 C23 C1 112.78(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C4 2.0374(18) . ?
Fe C2 2.0378(16) . ?
Fe C7 2.0397(19) . ?
Fe C1 2.0404(17) . ?
Fe C5 2.0406(18) . ?
Fe C6 2.0417(18) . ?
Fe C9 2.0435(18) . ?
Fe C3 2.0451(18) . ?
Fe C8 2.0453(18) . ?
Fe C10 2.0460(18) . ?
Cl C18 1.7405(18) . ?
C1 C5 1.428(3) . ?
C1 C2 1.429(2) . ?
C1 C23 1.499(2) . ?
C18 C19 1.361(2) . ?
C18 C17 1.402(2) . ?
N1 C12 1.459(2) . ?
N1 C11 1.481(2) . ?
C2 C3 1.427(2) . ?
C2 C11 1.491(3) . ?
C16 C17 1.364(2) . ?
C16 C15 1.414(2) . ?
C6 C10 1.408(3) . ?
C6 C7 1.417(3) . ?
C19 C20 1.409(2) . ?
C20 N3 1.369(2) . ?
C20 C15 1.419(2) . ?
C15 C14 1.439(2) . ?
N3 C21 1.317(2) . ?
C8 C9 1.411(3) . ?
C8 C7 1.417(3) . ?
N2 C14 1.355(2) . ?
N2 C13 1.453(2) . ?
C14 C22 1.393(2) . ?
C5 C4 1.415(3) . ?
C3 C4 1.412(3) . ?
C13 C12 1.523(2) . ?
C22 C21 1.395(3) . ?
C10 C9 1.414(3) . ?
N4 C25 1.450(2) . ?
N4 C24 1.465(2) . ?
N4 C23 1.469(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.9698(10) 2.111(7) 3.050(2) 162.6(18) 3_666
N1 H1 N4 0.9697(10) 2.288(8) 3.171(2) 151.1(14) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 Fe C1 C5 -37.53(13) . . . . ?
C2 Fe C1 C5 -119.22(15) . . . . ?
C7 Fe C1 C5 -168.77(17) . . . . ?
C6 Fe C1 C5 157.86(12) . . . . ?
C9 Fe C1 C5 74.76(14) . . . . ?
C3 Fe C1 C5 -81.13(13) . . . . ?
C8 Fe C1 C5 43.9(3) . . . . ?
C10 Fe C1 C5 115.51(12) . . . . ?
C4 Fe C1 C2 81.69(12) . . . . ?
C7 Fe C1 C2 -49.6(2) . . . . ?
C5 Fe C1 C2 119.22(15) . . . . ?
C6 Fe C1 C2 -82.92(12) . . . . ?
C9 Fe C1 C2 -166.02(10) . . . . ?
C3 Fe C1 C2 38.09(11) . . . . ?
C8 Fe C1 C2 163.1(2) . . . . ?
C10 Fe C1 C2 -125.27(11) . . . . ?
C4 Fe C1 C23 -159.91(19) . . . . ?
C2 Fe C1 C23 118.4(2) . . . . ?
C7 Fe C1 C23 68.9(2) . . . . ?
C5 Fe C1 C23 -122.4(2) . . . . ?
C6 Fe C1 C23 35.48(19) . . . . ?
C9 Fe C1 C23 -47.62(19) . . . . ?
C3 Fe C1 C23 156.49(19) . . . . ?
C8 Fe C1 C23 -78.5(3) . . . . ?
C10 Fe C1 C23 -6.86(18) . . . . ?
C5 C1 C2 C3 -0.60(18) . . . . ?
C23 C1 C2 C3 -179.03(15) . . . . ?
Fe C1 C2 C3 -59.74(11) . . . . ?
C5 C1 C2 C11 -178.88(15) . . . . ?
C23 C1 C2 C11 2.7(3) . . . . ?
Fe C1 C2 C11 121.97(16) . . . . ?
C5 C1 C2 Fe 59.15(12) . . . . ?
C23 C1 C2 Fe -119.29(16) . . . . ?
C4 Fe C2 C3 37.14(12) . . . . ?
C7 Fe C2 C3 -83.95(13) . . . . ?
C1 Fe C2 C3 118.67(15) . . . . ?
C5 Fe C2 C3 80.84(13) . . . . ?
C6 Fe C2 C3 -126.48(12) . . . . ?
C9 Fe C2 C3 162.8(3) . . . . ?
C8 Fe C2 C3 -50.7(2) . . . . ?
C10 Fe C2 C3 -166.86(12) . . . . ?
C4 Fe C2 C1 -81.53(12) . . . . ?
C7 Fe C2 C1 157.38(11) . . . . ?
C5 Fe C2 C1 -37.83(10) . . . . ?
C6 Fe C2 C1 114.84(11) . . . . ?
C9 Fe C2 C1 44.2(3) . . . . ?
C3 Fe C2 C1 -118.67(15) . . . . ?
C8 Fe C2 C1 -169.38(16) . . . . ?
C10 Fe C2 C1 74.47(13) . . . . ?
C4 Fe C2 C11 158.99(17) . . . . ?
C7 Fe C2 C11 37.90(18) . . . . ?
C1 Fe C2 C11 -119.48(19) . . . . ?
C5 Fe C2 C11 -157.31(17) . . . . ?
C6 Fe C2 C11 -4.63(17) . . . . ?
C9 Fe C2 C11 -75.3(3) . . . . ?
C3 Fe C2 C11 121.8(2) . . . . ?
C8 Fe C2 C11 71.1(2) . . . . ?
C10 Fe C2 C11 -45.01(18) . . . . ?
C4 Fe C6 C10 161.1(3) . . . . ?
C2 Fe C6 C10 -126.01(11) . . . . ?
C7 Fe C6 C10 118.85(17) . . . . ?
C1 Fe C6 C10 -83.01(13) . . . . ?
C5 Fe C6 C10 -48.8(2) . . . . ?
C9 Fe C6 C10 37.49(11) . . . . ?
C3 Fe C6 C10 -167.00(11) . . . . ?
C8 Fe C6 C10 81.13(12) . . . . ?
C4 Fe C6 C7 42.3(3) . . . . ?
C2 Fe C6 C7 115.14(12) . . . . ?
C1 Fe C6 C7 158.15(12) . . . . ?
C5 Fe C6 C7 -167.61(17) . . . . ?
C9 Fe C6 C7 -81.36(13) . . . . ?
C3 Fe C6 C7 74.15(14) . . . . ?
C8 Fe C6 C7 -37.71(12) . . . . ?
C10 Fe C6 C7 -118.85(17) . . . . ?
C17 C18 C19 C20 -2.9(3) . . . . ?
Cl C18 C19 C20 174.90(13) . . . . ?
C18 C19 C20 N3 -176.93(16) . . . . ?
C18 C19 C20 C15 1.9(2) . . . . ?
C17 C16 C15 C20 -2.1(2) . . . . ?
C17 C16 C15 C14 178.12(16) . . . . ?
N3 C20 C15 C16 179.28(16) . . . . ?
C19 C20 C15 C16 0.5(2) . . . . ?
N3 C20 C15 C14 -0.9(2) . . . . ?
C19 C20 C15 C14 -179.63(15) . . . . ?
C19 C20 N3 C21 177.98(16) . . . . ?
C15 C20 N3 C21 -0.8(3) . . . . ?
C4 Fe C8 C9 115.32(13) . . . . ?
C2 Fe C8 C9 -166.23(15) . . . . ?
C7 Fe C8 C9 -118.97(17) . . . . ?
C1 Fe C8 C9 39.6(3) . . . . ?
C5 Fe C8 C9 74.01(14) . . . . ?
C6 Fe C8 C9 -81.23(13) . . . . ?
C3 Fe C8 C9 158.00(12) . . . . ?
C10 Fe C8 C9 -37.66(12) . . . . ?
C4 Fe C8 C7 -125.72(13) . . . . ?
C2 Fe C8 C7 -47.3(2) . . . . ?
C1 Fe C8 C7 158.5(2) . . . . ?
C5 Fe C8 C7 -167.02(12) . . . . ?
C6 Fe C8 C7 37.74(12) . . . . ?
C9 Fe C8 C7 118.97(17) . . . . ?
C3 Fe C8 C7 -83.03(14) . . . . ?
C10 Fe C8 C7 81.31(13) . . . . ?
C12 N1 C11 C2 -175.38(14) . . . . ?
C3 C2 C11 N1 -97.46(19) . . . . ?
C1 C2 C11 N1 80.5(2) . . . . ?
Fe C2 C11 N1 170.66(11) . . . . ?
C13 N2 C14 C22 -1.0(3) . . . . ?
C13 N2 C14 C15 179.07(15) . . . . ?
C16 C15 C14 N2 1.9(2) . . . . ?
C20 C15 C14 N2 -177.94(15) . . . . ?
C16 C15 C14 C22 -178.01(16) . . . . ?
C20 C15 C14 C22 2.2(2) . . . . ?
C2 C1 C5 C4 0.09(19) . . . . ?
C23 C1 C5 C4 178.46(16) . . . . ?
Fe C1 C5 C4 59.17(12) . . . . ?
C2 C1 C5 Fe -59.07(12) . . . . ?
C23 C1 C5 Fe 119.30(17) . . . . ?
C2 Fe C5 C4 -81.48(13) . . . . ?
C7 Fe C5 C4 42.5(4) . . . . ?
C1 Fe C5 C4 -119.34(17) . . . . ?
C6 Fe C5 C4 -167.86(17) . . . . ?
C9 Fe C5 C4 115.42(13) . . . . ?
C3 Fe C5 C4 -37.40(12) . . . . ?
C8 Fe C5 C4 74.52(15) . . . . ?
C10 Fe C5 C4 158.02(12) . . . . ?
C4 Fe C5 C1 119.34(17) . . . . ?
C2 Fe C5 C1 37.86(10) . . . . ?
C7 Fe C5 C1 161.9(3) . . . . ?
C6 Fe C5 C1 -48.5(2) . . . . ?
C9 Fe C5 C1 -125.24(11) . . . . ?
C3 Fe C5 C1 81.94(12) . . . . ?
C8 Fe C5 C1 -166.14(11) . . . . ?
C10 Fe C5 C1 -82.64(13) . . . . ?
C1 C2 C3 C4 0.88(19) . . . . ?
C11 C2 C3 C4 179.12(16) . . . . ?
Fe C2 C3 C4 -58.72(13) . . . . ?
C1 C2 C3 Fe 59.60(11) . . . . ?
C11 C2 C3 Fe -122.16(16) . . . . ?
C2 Fe C3 C4 119.91(16) . . . . ?
C7 Fe C3 C4 -125.86(12) . . . . ?
C1 Fe C3 C4 81.73(12) . . . . ?
C5 Fe C3 C4 37.53(11) . . . . ?
C6 Fe C3 C4 -167.07(11) . . . . ?
C9 Fe C3 C4 -49.2(2) . . . . ?
C8 Fe C3 C4 -83.07(14) . . . . ?
C10 Fe C3 C4 161.3(3) . . . . ?
C4 Fe C3 C2 -119.91(16) . . . . ?
C7 Fe C3 C2 114.23(12) . . . . ?
C1 Fe C3 C2 -38.18(11) . . . . ?
C5 Fe C3 C2 -82.38(12) . . . . ?
C6 Fe C3 C2 73.02(13) . . . . ?
C9 Fe C3 C2 -169.08(16) . . . . ?
C8 Fe C3 C2 157.02(11) . . . . ?
C10 Fe C3 C2 41.4(3) . . . . ?
C14 N2 C13 C12 -73.0(2) . . . . ?
C10 C6 C7 C8 -0.2(2) . . . . ?
Fe C6 C7 C8 59.64(13) . . . . ?
C10 C6 C7 Fe -59.84(12) . . . . ?
C9 C8 C7 C6 0.0(2) . . . . ?
Fe C8 C7 C6 -59.55(12) . . . . ?
C9 C8 C7 Fe 59.50(12) . . . . ?
C4 Fe C7 C6 -166.68(12) . . . . ?
C2 Fe C7 C6 -82.47(13) . . . . ?
C1 Fe C7 C6 -47.5(2) . . . . ?
C5 Fe C7 C6 160.0(3) . . . . ?
C9 Fe C7 C6 81.48(13) . . . . ?
C3 Fe C7 C6 -125.69(12) . . . . ?
C8 Fe C7 C6 119.15(17) . . . . ?
C10 Fe C7 C6 37.68(12) . . . . ?
C4 Fe C7 C8 74.17(15) . . . . ?
C2 Fe C7 C8 158.38(11) . . . . ?
C1 Fe C7 C8 -166.67(15) . . . . ?
C5 Fe C7 C8 40.9(4) . . . . ?
C6 Fe C7 C8 -119.15(17) . . . . ?
C9 Fe C7 C8 -37.68(11) . . . . ?
C3 Fe C7 C8 115.16(12) . . . . ?
C10 Fe C7 C8 -81.47(13) . . . . ?
C11 N1 C12 C13 -175.90(14) . . . . ?
N2 C13 C12 N1 -51.6(2) . . . . ?
N2 C14 C22 C21 178.26(17) . . . . ?
C15 C14 C22 C21 -1.8(2) . . . . ?
C20 N3 C21 C22 1.2(3) . . . . ?
C14 C22 C21 N3 0.2(3) . . . . ?
C15 C16 C17 C18 1.1(3) . . . . ?
C19 C18 C17 C16 1.4(3) . . . . ?
Cl C18 C17 C16 -176.47(14) . . . . ?
C7 C6 C10 C9 0.4(2) . . . . ?
Fe C6 C10 C9 -59.22(12) . . . . ?
C7 C6 C10 Fe 59.59(13) . . . . ?
C4 Fe C10 C6 -168.13(16) . . . . ?
C2 Fe C10 C6 73.02(13) . . . . ?
C7 Fe C10 C6 -37.98(12) . . . . ?
C1 Fe C10 C6 114.58(12) . . . . ?
C5 Fe C10 C6 157.62(11) . . . . ?
C9 Fe C10 C6 -119.52(17) . . . . ?
C3 Fe C10 C6 40.6(3) . . . . ?
C8 Fe C10 C6 -81.93(13) . . . . ?
C4 Fe C10 C9 -48.6(2) . . . . ?
C2 Fe C10 C9 -167.46(11) . . . . ?
C7 Fe C10 C9 81.54(13) . . . . ?
C1 Fe C10 C9 -125.90(12) . . . . ?
C5 Fe C10 C9 -82.86(13) . . . . ?
C6 Fe C10 C9 119.52(17) . . . . ?
C3 Fe C10 C9 160.1(3) . . . . ?
C8 Fe C10 C9 37.59(12) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
Fe C3 C4 C5 -59.43(13) . . . . ?
C2 C3 C4 Fe 58.60(12) . . . . ?
C1 C5 C4 C3 0.5(2) . . . . ?
Fe C5 C4 C3 59.58(13) . . . . ?
C1 C5 C4 Fe -59.12(12) . . . . ?
C2 Fe C4 C3 -37.53(11) . . . . ?
C7 Fe C4 C3 73.89(14) . . . . ?
C1 Fe C4 C3 -81.70(12) . . . . ?
C5 Fe C4 C3 -119.56(16) . . . . ?
C6 Fe C4 C3 40.8(3) . . . . ?
C9 Fe C4 C3 157.65(11) . . . . ?
C8 Fe C4 C3 115.09(12) . . . . ?
C10 Fe C4 C3 -168.15(16) . . . . ?
C2 Fe C4 C5 82.03(12) . . . . ?
C7 Fe C4 C5 -166.55(12) . . . . ?
C1 Fe C4 C5 37.86(11) . . . . ?
C6 Fe C4 C5 160.4(3) . . . . ?
C9 Fe C4 C5 -82.79(13) . . . . ?
C3 Fe C4 C5 119.56(16) . . . . ?
C8 Fe C4 C5 -125.34(12) . . . . ?
C10 Fe C4 C5 -48.6(2) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
Fe C8 C9 C10 59.61(13) . . . . ?
C7 C8 C9 Fe -59.34(12) . . . . ?
C6 C10 C9 C8 -0.4(2) . . . . ?
Fe C10 C9 C8 -59.62(12) . . . . ?
C6 C10 C9 Fe 59.22(12) . . . . ?
C4 Fe C9 C8 -82.84(14) . . . . ?
C2 Fe C9 C8 158.1(2) . . . . ?
C7 Fe C9 C8 37.87(12) . . . . ?
C1 Fe C9 C8 -167.30(12) . . . . ?
C5 Fe C9 C8 -125.60(12) . . . . ?
C6 Fe C9 C8 81.83(13) . . . . ?
C3 Fe C9 C8 -48.3(2) . . . . ?
C10 Fe C9 C8 119.19(17) . . . . ?
C4 Fe C9 C10 157.98(12) . . . . ?
C2 Fe C9 C10 38.9(3) . . . . ?
C7 Fe C9 C10 -81.31(13) . . . . ?
C1 Fe C9 C10 73.51(14) . . . . ?
C5 Fe C9 C10 115.21(12) . . . . ?
C6 Fe C9 C10 -37.35(12) . . . . ?
C3 Fe C9 C10 -167.47(17) . . . . ?
C8 Fe C9 C10 -119.19(17) . . . . ?
C25 N4 C23 C1 -72.9(2) . . . . ?
C24 N4 C23 C1 165.56(16) . . . . ?
C5 C1 C23 N4 114.2(2) . . . . ?
C2 C1 C23 N4 -67.7(2) . . . . ?
Fe C1 C23 N4 -155.55(13) . . . . ?
