Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name 'John Moss' 'Paul Beagley' 'Margaret A.L. Blackie' 'Kelly Chibale' 'Cailean Clarkson' ; R.Meijboom ; 'Peter J. Smith' 'Hong Su' _publ_contact_author_name 'Prof John Moss' _publ_contact_author_address ; Dept of Chemistry University of Cape Town Rondesbosch 7701 SOUTH AFRICA ; _publ_contact_author_email JRM@SCIENCE.UCT.AC.ZA _publ_section_title ; Synthesis and Antiplasmodial Activity in vitro of New Ferrocene-chloroquine Analogues ; data_structure_4a _database_code_CSD 206811 _chemical_name_common ;7-chloroquinolin-4-yl)-N'-(1'-dimethylaminomethylferrocen-1- ylmethyl)-amine ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-chloroquinolin-4-yl)-N'-(1'-dimethylaminomethylferrocen-1-ylmethyl)-amine ; _chemical_formula_sum 'C23 H26 Cl Fe N3 O' _chemical_formula_weight 451.77 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' _cell_length_a 26.3704(2) _cell_length_b 9.2289(3) _cell_length_c 21.7319(4) _cell_angle_alpha 90.00 _cell_angle_beta 127.2210(10) _cell_angle_gamma 90.00 _cell_volume 4211.58(16) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas N/A _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1888 _exptl_absorpt_coefficient_mu 0.862 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40mm; combination of \f and \w scans of 1\%, 40s per \%, 2 iterations. ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.0\% \f scans and \w scans' _diffrn_reflns_number 32757 _diffrn_reflns_av_R_equivalents 0.0670 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4830 _reflns_number_gt 3594 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PovRay _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0776P)^2^+0.0727P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _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_number_reflns 4830 _refine_ls_number_parameters 277 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0763 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1372 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.182 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 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) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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_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_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) . . . . ? 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 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.743 _refine_diff_density_min -0.859 _refine_diff_density_rms 0.243 #===END data_structure_5a _database_code_CSD 206812 _chemical_name_common ; N-(7-chloro-quinolin-4-yl)-N’-(2-dimethylaminomethylferrocen- 1-ylmethyl) -ethane-1,2-diamine ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(7-chloro-quinolin-4-yl)-N’-(2-dimethylaminomethylferrocen-1-ylmethyl) -ethane-1,2-diamine ; _chemical_formula_sum 'C25 H29 Cl Fe N4' _chemical_formula_weight 476.82 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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' _cell_length_a 10.7012(3) _cell_length_b 16.2573(4) _cell_length_c 13.7853(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.7270(10) _cell_angle_gamma 90.00 _cell_volume 2395.55(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas N/A _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.760 _exptl_special_details ; Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40mm; combination of \f and \w scans of 1\%, 20s per \%, 2 iterations. ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method '1.0\% \f scans and \w scans' _diffrn_reflns_number 10265 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5459 _reflns_number_gt 4107 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (2000)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PovRay _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.6881P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _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_number_reflns 5459 _refine_ls_number_parameters 291 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0825 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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_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_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) . . . . ? 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) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.235 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.046