data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Peter Scott' 'Guy J Clarkson' 'Suzanne E Howson' 'Cynthia Paul Sebli' _publ_contact_author_name 'Peter Scott' _publ_contact_author_email PETER.SCOTT@WARWICK.AC.UK _publ_section_title ; fac-Specific syntheses of homochiral [Fe(NN')3]2+ complexes (NN' = pyridine keto-hydrazone); origins of the stereoselectivity ; # Attachment 'c3a.cif' data_c3a _database_code_depnum_ccdc_archive 'CCDC 761423' #TrackingRef 'c3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H39 Cl2 Fe N9 O8' _chemical_formula_weight 888.54 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 hexagonal _symmetry_space_group_name_H-M P6(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' _cell_length_a 15.8761(4) _cell_length_b 15.8761(4) _cell_length_c 10.5809(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2309.63(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4055 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 32.50 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.498 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'ABSPACK(CrysAlis, Oxford Diffraction)' _exptl_special_details ; The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cobra. The data collection nominally covered over a hemisphere of Reciprocal space, by a combination of four sets of exposures with different \f angles for the crystal; each 10 s exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.5 cm. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms; H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 10.2833 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 11159 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0679 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 32.58 _reflns_number_total 3969 _reflns_number_gt 2842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (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^)+(0.0996P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 1206 Friedel pairs' _refine_ls_abs_structure_Flack 0.03(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 3969 _refine_ls_number_parameters 208 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0778 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1520 _refine_ls_wR_factor_gt 0.1437 _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_restrained_S_all 0.972 _refine_ls_shift/su_max 0.000 _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 0.3333 0.6667 0.23844(7) 0.01927(18) Uani 1 3 d S . . N1 N 0.30983(18) 0.75944(17) 0.3356(3) 0.0202(5) Uani 1 1 d . . . C1 C 0.3525(2) 0.8061(2) 0.4417(4) 0.0247(6) Uani 1 1 d . . . H1A H 0.3997 0.7943 0.4800 0.030 Uiso 1 1 calc R . . C2 C 0.3303(2) 0.8715(2) 0.4985(5) 0.0331(8) Uani 1 1 d . . . H2A H 0.3613 0.9023 0.5754 0.040 Uiso 1 1 calc R . . C3 C 0.2643(3) 0.8917(3) 0.4446(5) 0.0445(11) Uani 1 1 d . . . H3A H 0.2491 0.9367 0.4827 0.053 Uiso 1 1 calc R . . C4 C 0.2196(3) 0.8446(3) 0.3318(5) 0.0384(9) Uani 1 1 d . . . H4A H 0.1738 0.8575 0.2912 0.046 Uiso 1 1 calc R . . C5 C 0.2434(2) 0.7783(2) 0.2799(4) 0.0273(7) Uani 1 1 d . . . C6 C 0.1953(2) 0.7192(2) 0.1698(4) 0.0276(7) Uani 1 1 d . . . C7 C 0.1190(3) 0.7284(3) 0.0995(5) 0.0415(10) Uani 1 1 d . . . H7A H 0.0975 0.6844 0.0267 0.062 Uiso 1 1 calc R . . H7B H 0.1457 0.7956 0.0702 0.062 Uiso 1 1 calc R . . H7C H 0.0635 0.7114 0.1555 0.062 Uiso 1 1 calc R . . N2 N 0.22457(18) 0.65791(18) 0.1428(3) 0.0230(5) Uani 1 1 d . . . N3 N 0.1697(2) 0.5879(2) 0.0502(3) 0.0287(6) Uani 1 1 d . . . H3B H 0.1883 0.5970 -0.0294 0.034 Uiso 1 1 calc R . . C8 C 0.0846(2) 0.5033(2) 0.0881(3) 0.0233(6) Uani 1 1 d . . . C9 C 0.0511(2) 0.4218(2) 0.0080(5) 0.0302(7) Uani 1 1 d . . . H9A H 0.0870 0.4242 -0.0651 0.036 Uiso 1 1 calc R . . C10 C -0.0348(3) 0.3383(3) 0.0377(4) 0.0421(11) Uani 1 1 d . . . H10A H -0.0585 0.2837 -0.0171 0.050 Uiso 1 1 calc R . . C11 C -0.0877(3) 0.3322(3) 0.1461(5) 0.0428(10) Uani 1 1 d . . . H11A H -0.1459 0.2736 0.1658 0.051 Uiso 1 1 calc R . . C12 C -0.0548(2) 0.4115(2) 0.2237(4) 0.0318(8) Uani 1 1 d . . . H12A H -0.0908 0.4082 0.2971 0.038 Uiso 1 1 calc R . . C13 C 0.0318(2) 0.4976(2) 0.1952(4) 0.0265(7) Uani 1 1 d . . . H13A H 0.0543 0.5523 0.2497 0.032 Uiso 1 1 calc R . . Cl1 Cl 0.3333 0.6667 -0.21559(15) 0.0303(3) Uani 1 3 d S . . O1 O 0.2733(2) 0.56905(19) -0.1688(3) 0.0372(6) Uani 1 1 d . . . O2 O 0.3333 0.6667 -0.3500(5) 0.0448(13) Uani 1 3 d S . . Cl2 Cl 0.80004(17) 0.87232(16) 0.7764(3) 0.0322(6) Uani 0.33 1 d PD . . O3 O 0.8326(10) 0.8979(11) 0.6490(13) 0.095(4) Uani 0.33 1 d PDU . . O4 O 0.8580(9) 0.8489(10) 0.8531(15) 0.090(4) Uani 0.33 1 d PDU . . O5 O 0.8019(10) 0.9546(9) 0.8237(15) 0.087(4) Uani 0.33 1 d PDU . . O6 O 0.7149(7) 0.7878(6) 0.7717(10) 0.066(3) Uani 0.33 1 d PDU . . 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 0.0207(2) 0.0207(2) 0.0163(4) 0.000 0.000 0.01037(10) N1 0.0192(11) 0.0190(11) 0.0207(13) -0.0007(11) -0.0018(11) 0.0083(9) C1 0.0216(14) 0.0265(15) 0.0230(16) -0.0009(14) -0.0001(14) 0.0098(12) C2 0.0299(15) 0.0310(15) 0.036(2) -0.0153(18) -0.0099(18) 0.0138(13) C3 0.040(2) 0.042(2) 0.058(3) -0.027(2) -0.015(2) 0.0263(18) C4 0.0334(17) 0.0369(18) 0.052(3) -0.0200(19) -0.0177(19) 0.0228(16) C5 0.0252(14) 0.0268(14) 0.0299(18) -0.0056(14) -0.0065(14) 0.0130(12) C6 0.0263(14) 0.0295(16) 0.029(2) -0.0037(14) -0.0064(14) 0.0154(13) C7 0.045(2) 0.046(2) 0.046(3) -0.013(2) -0.021(2) 0.0310(19) N2 0.0255(12) 0.0230(12) 0.0177(13) -0.0036(11) -0.0019(12) 0.0100(10) N3 0.0282(13) 0.0306(14) 0.0178(13) -0.0070(12) -0.0039(12) 0.0076(11) C8 0.0229(14) 0.0264(15) 0.0198(15) -0.0015(13) -0.0037(13) 0.0117(12) C9 0.0397(16) 0.0272(14) 0.0261(17) -0.0069(18) -0.0034(19) 0.0186(13) C10 0.051(2) 0.0223(15) 0.042(3) -0.0041(17) 0.001(2) 0.0102(15) C11 0.040(2) 0.0320(18) 0.043(3) 0.0035(19) 0.002(2) 0.0079(16) C12 0.0280(14) 0.0394(17) 0.029(2) 0.0020(17) 0.0015(16) 0.0178(13) C13 0.0264(14) 0.0313(15) 0.0234(16) -0.0059(14) -0.0053(14) 0.0156(12) Cl1 0.0372(4) 0.0372(4) 0.0164(7) 0.000 0.000 0.0186(2) O1 0.0422(14) 0.0357(13) 0.0312(15) -0.0009(12) 0.0068(13) 0.0176(11) O2 0.0596(19) 0.0596(19) 0.015(2) 0.000 0.000 0.0298(10) Cl2 0.0312(10) 0.0227(9) 0.0476(17) -0.0071(11) -0.0054(11) 0.0171(9) O3 0.074(6) 0.109(7) 0.088(7) -0.002(5) -0.004(5) 0.036(5) O4 0.077(6) 0.090(6) 0.104(7) 0.017(5) -0.013(5) 0.044(5) O5 0.090(6) 0.086(6) 0.099(7) -0.025(5) -0.014(5) 0.055(5) O6 0.090(5) 0.026(3) 0.039(5) -0.002(3) -0.015(4) -0.004(3) _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 N2 1.946(3) . ? Fe1 N2 1.946(3) 3_565 ? Fe1 N2 1.946(3) 2_665 ? Fe1 N1 1.978(3) . ? Fe1 N1 1.978(3) 2_665 ? Fe1 N1 1.978(3) 3_565 ? N1 C1 1.329(5) . ? N1 C5 1.366(4) . ? C1 C2 1.388(5) . ? C1 H1A 0.9500 . ? C2 C3 1.366(6) . ? C2 H2A 0.9500 . ? C3 C4 1.399(6) . ? C3 H3A 0.9500 . ? C4 C5 1.396(5) . ? C4 H4A 0.9500 . ? C5 C6 1.451(5) . ? C6 N2 1.303(4) . ? C6 C7 1.490(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N2 N3 1.409(4) . ? N3 C8 1.406(4) . ? N3 H3B 0.8800 . ? C8 C13 1.385(5) . ? C8 C9 1.411(5) . ? C9 C10 1.381(5) . ? C9 H9A 0.9500 . ? C10 C11 1.396(7) . ? C10 H10A 0.9500 . ? C11 C12 1.369(6) . ? C11 H11A 0.9500 . ? C12 C13 1.404(5) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? Cl1 O2 1.422(6) . ? Cl1 O1 1.442(3) 3_565 ? Cl1 O1 1.442(3) 2_665 ? Cl1 O1 1.442(3) . ? Cl2 O6 1.348(8) . ? Cl2 O5 1.386(10) . ? Cl2 O4 1.409(11) . ? Cl2 O3 1.428(13) . ? 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 N2 Fe1 N2 95.38(12) . 3_565 ? N2 Fe1 N2 95.38(12) . 2_665 ? N2 Fe1 N2 95.38(12) 3_565 2_665 ? N2 Fe1 N1 80.36(11) . . ? N2 Fe1 N1 89.06(11) 3_565 . ? N2 Fe1 N1 174.14(10) 2_665 . ? N2 Fe1 N1 89.06(11) . 2_665 ? N2 Fe1 N1 174.14(10) 3_565 2_665 ? N2 Fe1 N1 80.36(11) 2_665 2_665 ? N1 Fe1 N1 95.47(12) . 2_665 ? N2 Fe1 N1 174.14(10) . 3_565 ? N2 Fe1 N1 80.36(11) 3_565 3_565 ? N2 Fe1 N1 89.06(11) 2_665 3_565 ? N1 Fe1 N1 95.47(12) . 3_565 ? N1 Fe1 N1 95.47(12) 2_665 3_565 ? C1 N1 C5 118.4(3) . . ? C1 N1 Fe1 128.4(2) . . ? C5 N1 Fe1 113.2(2) . . ? N1 C1 C2 122.3(3) . . ? N1 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C3 C2 C1 120.4(4) . . ? C3 C2 H2A 119.8 . . ? C1 C2 H2A 119.8 . . ? C2 C3 C4 118.3(4) . . ? C2 C3 H3A 120.8 . . ? C4 C3 H3A 120.8 . . ? C5 C4 C3 118.8(3) . . ? C5 C4 H4A 120.6 . . ? C3 C4 H4A 120.6 . . ? N1 C5 C4 121.7(3) . . ? N1 C5 C6 114.8(3) . . ? C4 C5 C6 123.4(3) . . ? N2 C6 C5 113.0(3) . . ? N2 C6 C7 125.1(3) . . ? C5 C6 C7 121.9(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 N2 N3 115.5(3) . . ? C6 N2 Fe1 117.9(2) . . ? N3 N2 Fe1 126.5(2) . . ? C8 N3 N2 118.3(3) . . ? C8 N3 H3B 120.8 . . ? N2 N3 H3B 120.8 . . ? C13 C8 N3 123.9(3) . . ? C13 C8 C9 119.6(3) . . ? N3 C8 C9 116.5(3) . . ? C10 C9 C8 118.8(4) . . ? C10 C9 H9A 120.6 . . ? C8 C9 H9A 120.6 . . ? C9 C10 C11 121.7(4) . . ? C9 C10 H10A 119.1 . . ? C11 C10 H10A 119.1 . . ? C12 C11 C10 119.2(4) . . ? C12 C11 H11A 120.4 . . ? C10 C11 H11A 120.4 . . ? C11 C12 C13 120.3(4) . . ? C11 C12 H12A 119.8 . . ? C13 C12 H12A 119.8 . . ? C8 C13 C12 120.3(3) . . ? C8 C13 H13A 119.8 . . ? C12 C13 H13A 119.8 . . ? O2 Cl1 O1 110.11(14) . 3_565 ? O2 Cl1 O1 110.11(14) . 2_665 ? O1 Cl1 O1 108.83(14) 3_565 2_665 ? O2 Cl1 O1 110.11(14) . . ? O1 Cl1 O1 108.83(14) 3_565 . ? O1 Cl1 O1 108.83(14) 2_665 . ? O6 Cl2 O5 119.3(8) . . ? O6 Cl2 O4 102.8(7) . . ? O5 Cl2 O4 109.4(9) . . ? O6 Cl2 O3 106.8(8) . . ? O5 Cl2 O3 103.8(9) . . ? O4 Cl2 O3 115.3(9) . . ? 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 N3 H3B O1 0.88 2.19 2.942(4) 143.3 . N3 H3B O1 0.88 2.41 3.133(5) 139.5 3_565 C1 H1A O2 0.95 2.51 3.030(5) 114.2 1_556 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.751 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.088 # Attachment 'c4a.cif' data_c4a _database_code_depnum_ccdc_archive 'CCDC 761424' #TrackingRef 'c4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H39 B2 F8 Fe N9' _chemical_formula_weight 863.26 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 hexagonal _symmetry_space_group_name_H-M P6(3) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' _cell_length_a 15.8761(4) _cell_length_b 15.8761(4) _cell_length_c 10.5809(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2309.63(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3994 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 29.33 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.395 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'ABSPACK(CrysAlis, Oxford Diffraction)' _exptl_special_details ; The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cobra. The data collection nominally covered over a hemisphere of Reciprocal space, by a combination of four sets of exposures with different \f angles for the crystal; each 10 s exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.5 cm. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms; H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 10.2833 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 8792 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0855 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 29.28 _reflns_number_total 3502 _reflns_number_gt 2578 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (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^)+(0.0995P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 1477 Friedel pairs' _refine_ls_abs_structure_Flack 0.03(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 3502 _refine_ls_number_parameters 208 _refine_ls_number_restraints 35 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0599 _refine_ls_wR_factor_ref 0.1535 _refine_ls_wR_factor_gt 0.1470 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.996 _refine_ls_shift/su_max 0.000 _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 0.3333 0.6667 0.23901(8) 0.0163(2) Uani 1 3 d S . . N1 N 0.3093(2) 0.7584(2) 0.3357(3) 0.0203(7) Uani 1 1 d . . . C1 C 0.3517(3) 0.8059(3) 0.4450(4) 0.0232(8) Uani 1 1 d . . . H1A H 0.3989 0.7942 0.4836 0.028 Uiso 1 1 calc R . . C2 C 0.3289(3) 0.8706(3) 0.5029(5) 0.0374(11) Uani 1 1 d . . . H2A H 0.3573 0.8998 0.5816 0.045 Uiso 1 1 calc R . . C3 C 0.2650(3) 0.8912(3) 0.4440(6) 0.0481(15) Uani 1 1 d . . . H3A H 0.2511 0.9379 0.4792 0.058 Uiso 1 1 calc R . . C4 C 0.2204(3) 0.8439(3) 0.3327(6) 0.0395(12) Uani 1 1 d . . . H4A H 0.1745 0.8567 0.2924 0.047 Uiso 1 1 calc R . . C5 C 0.2432(3) 0.7777(3) 0.2806(4) 0.0260(9) Uani 1 1 d . . . C6 C 0.1956(3) 0.7173(3) 0.1684(4) 0.0261(9) Uani 1 1 d . . . C7 C 0.1185(4) 0.7270(4) 0.0980(6) 0.0450(13) Uani 1 1 d . . . H7A H 0.0967 0.6832 0.0250 0.068 Uiso 1 1 calc R . . H7B H 0.1455 0.7943 0.0689 0.068 Uiso 1 1 calc R . . H7C H 0.0633 0.7101 0.1543 0.068 Uiso 1 1 calc R . . N2 N 0.2249(2) 0.6576(2) 0.1402(3) 0.0206(7) Uani 1 1 d . . . N3 N 0.1712(2) 0.5871(3) 0.0477(3) 0.0258(8) Uani 1 1 d . . . H3B H 0.1910 0.5957 -0.0313 0.031 Uiso 1 1 calc R . . C8 C 0.0862(3) 0.5034(3) 0.0837(4) 0.0237(8) Uani 1 1 d . . . C9 C 0.0533(3) 0.4216(3) 0.0040(5) 0.0289(9) Uani 1 1 d . . . H9A H 0.0894 0.4241 -0.0689 0.035 Uiso 1 1 calc R . . C10 C -0.0316(4) 0.3384(3) 0.0336(5) 0.0448(13) Uani 1 1 d . . . H10A H -0.0553 0.2840 -0.0215 0.054 Uiso 1 1 calc R . . C11 C -0.0843(3) 0.3317(3) 0.1427(5) 0.0398(11) Uani 1 1 d . . . H11A H -0.1417 0.2725 0.1628 0.048 Uiso 1 1 calc R . . C12 C -0.0529(3) 0.4105(3) 0.2201(4) 0.0313(10) Uani 1 1 d . . . H12A H -0.0898 0.4070 0.2927 0.038 Uiso 1 1 calc R . . C13 C 0.0326(3) 0.4957(3) 0.1932(4) 0.0261(9) Uani 1 1 d . . . H13A H 0.0554 0.5494 0.2493 0.031 Uiso 1 1 calc R . . B1 B 0.3333 0.6667 -0.2170(9) 0.038(2) Uani 1 3 d S . . F1 F 0.27633(19) 0.57292(19) -0.1686(3) 0.0408(6) Uani 1 1 d . . . F2 F 0.3333 0.6667 -0.3460(5) 0.0473(14) Uani 1 3 d S . . B2 B 0.8008(12) 0.8693(11) 0.7696(16) 0.0733(17) Uani 0.33 1 d PDU . . F3 F 0.8250(8) 0.8983(7) 0.6476(12) 0.0764(18) Uani 0.33 1 d PDU . . F4 F 0.8467(7) 0.8299(7) 0.8359(12) 0.0739(18) Uani 0.33 1 d PDU . . F5 F 0.7936(8) 0.9367(7) 0.8450(11) 0.0716(18) Uani 0.33 1 d PDU . . F6 F 0.7032(7) 0.7852(7) 0.7654(12) 0.0754(18) Uani 0.33 1 d PDU . . 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 0.0157(3) 0.0157(3) 0.0175(4) 0.000 0.000 0.00786(14) N1 0.0157(15) 0.0141(15) 0.0296(18) -0.0029(14) -0.0041(14) 0.0064(13) C1 0.0125(17) 0.0178(18) 0.032(2) -0.0032(17) -0.0019(17) 0.0020(15) C2 0.026(2) 0.034(2) 0.045(3) -0.023(2) -0.010(2) 0.010(2) C3 0.031(2) 0.035(3) 0.085(4) -0.040(3) -0.016(3) 0.021(2) C4 0.028(2) 0.029(2) 0.068(3) -0.023(2) -0.018(2) 0.019(2) C5 0.0145(17) 0.0228(19) 0.040(2) -0.0074(17) -0.0063(15) 0.0086(16) C6 0.0184(19) 0.028(2) 0.034(2) -0.0050(18) -0.0099(17) 0.0132(17) C7 0.036(3) 0.049(3) 0.061(4) -0.017(3) -0.025(2) 0.029(2) N2 0.0195(16) 0.0194(16) 0.0185(16) -0.0011(13) -0.0046(13) 0.0065(14) N3 0.0228(17) 0.0290(18) 0.0186(16) -0.0076(14) -0.0045(14) 0.0077(15) C8 0.022(2) 0.027(2) 0.026(2) -0.0031(16) -0.0079(16) 0.0147(18) C9 0.028(2) 0.028(2) 0.031(2) -0.0059(19) -0.0064(18) 0.0141(18) C10 0.053(3) 0.024(2) 0.048(3) -0.011(2) -0.013(2) 0.012(2) C11 0.031(2) 0.025(2) 0.046(3) 0.002(2) -0.005(2) 0.0003(19) C12 0.0214(19) 0.039(2) 0.034(3) 0.001(2) -0.0036(18) 0.0152(17) C13 0.0227(19) 0.030(2) 0.028(2) -0.0059(16) -0.0052(16) 0.0155(17) B1 0.045(3) 0.045(3) 0.024(5) 0.000 0.000 0.0223(17) F1 0.0441(15) 0.0373(15) 0.0365(15) -0.0033(12) 0.0075(13) 0.0170(12) F2 0.060(2) 0.060(2) 0.023(3) 0.000 0.000 0.0298(11) B2 0.071(3) 0.056(3) 0.104(4) -0.042(3) -0.040(3) 0.040(3) F3 0.072(3) 0.059(3) 0.105(4) -0.041(3) -0.040(3) 0.038(3) F4 0.071(3) 0.057(3) 0.105(4) -0.040(3) -0.040(3) 0.041(3) F5 0.071(3) 0.054(3) 0.103(4) -0.045(3) -0.040(3) 0.042(3) F6 0.074(3) 0.055(3) 0.103(4) -0.042(3) -0.041(3) 0.037(3) _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 N2 1.957(3) . ? Fe1 N2 1.957(3) 3_565 ? Fe1 N2 1.957(3) 2_665 ? Fe1 N1 1.967(3) . ? Fe1 N1 1.967(3) 2_665 ? Fe1 N1 1.967(3) 3_565 ? N1 C1 1.361(5) . ? N1 C5 1.362(5) . ? C1 C2 1.391(6) . ? C1 H1A 0.9500 . ? C2 C3 1.362(7) . ? C2 H2A 0.9500 . ? C3 C4 1.386(7) . ? C3 H3A 0.9500 . ? C4 C5 1.386(6) . ? C4 H4A 0.9500 . ? C5 C6 1.475(6) . ? C6 N2 1.282(5) . ? C6 C7 1.505(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N2 N3 1.409(4) . ? N3 C8 1.392(5) . ? N3 H3B 0.8800 . ? C8 C13 1.406(6) . ? C8 C9 1.411(6) . ? C9 C10 1.371(6) . ? C9 H9A 0.9500 . ? C10 C11 1.398(8) . ? C10 H10A 0.9500 . ? C11 C12 1.365(7) . ? C11 H11A 0.9500 . ? C12 C13 1.385(6) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? B1 F2 1.364(12) . ? B1 F1 1.396(5) 3_565 ? B1 F1 1.396(5) . ? B1 F1 1.396(5) 2_665 ? B2 F3 1.360(16) . ? B2 F4 1.368(15) . ? B2 F5 1.384(15) . ? B2 F6 1.455(16) . ? 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 N2 Fe1 N2 94.13(14) . 3_565 ? N2 Fe1 N2 94.13(14) . 2_665 ? N2 Fe1 N2 94.13(14) 3_565 2_665 ? N2 Fe1 N1 80.97(13) . . ? N2 Fe1 N1 89.77(13) 3_565 . ? N2 Fe1 N1 173.96(13) 2_665 . ? N2 Fe1 N1 89.77(13) . 2_665 ? N2 Fe1 N1 173.96(13) 3_565 2_665 ? N2 Fe1 N1 80.97(13) 2_665 2_665 ? N1 Fe1 N1 95.40(14) . 2_665 ? N2 Fe1 N1 173.96(13) . 3_565 ? N2 Fe1 N1 80.97(13) 3_565 3_565 ? N2 Fe1 N1 89.77(13) 2_665 3_565 ? N1 Fe1 N1 95.40(14) . 3_565 ? N1 Fe1 N1 95.40(14) 2_665 3_565 ? C1 N1 C5 117.5(3) . . ? C1 N1 Fe1 128.8(3) . . ? C5 N1 Fe1 113.6(3) . . ? N1 C1 C2 123.0(4) . . ? N1 C1 H1A 118.5 . . ? C2 C1 H1A 118.5 . . ? C3 C2 C1 118.4(4) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C2 C3 C4 120.0(4) . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 119.4(4) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? N1 C5 C4 121.6(4) . . ? N1 C5 C6 113.6(3) . . ? C4 C5 C6 124.7(4) . . ? N2 C6 C5 114.2(3) . . ? N2 C6 C7 125.1(4) . . ? C5 C6 C7 120.7(4) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 N2 N3 116.8(3) . . ? C6 N2 Fe1 116.9(3) . . ? N3 N2 Fe1 126.1(3) . . ? C8 N3 N2 118.8(3) . . ? C8 N3 H3B 120.6 . . ? N2 N3 H3B 120.6 . . ? N3 C8 C13 124.3(4) . . ? N3 C8 C9 116.8(4) . . ? C13 C8 C9 118.8(4) . . ? C10 C9 C8 118.9(4) . . ? C10 C9 H9A 120.6 . . ? C8 C9 H9A 120.6 . . ? C9 C10 C11 121.7(4) . . ? C9 C10 H10A 119.2 . . ? C11 C10 H10A 119.2 . . ? C12 C11 C10 119.7(4) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 120.1(4) . . ? C11 C12 H12A 119.9 . . ? C13 C12 H12A 119.9 . . ? C12 C13 C8 120.7(4) . . ? C12 C13 H13A 119.6 . . ? C8 C13 H13A 119.6 . . ? F2 B1 F1 111.5(4) . 3_565 ? F2 B1 F1 111.5(4) . . ? F1 B1 F1 107.4(4) 3_565 . ? F2 B1 F1 111.5(4) . 2_665 ? F1 B1 F1 107.4(4) 3_565 2_665 ? F1 B1 F1 107.4(4) . 2_665 ? F3 B2 F4 121.1(14) . . ? F3 B2 F5 113.8(13) . . ? F4 B2 F5 109.0(12) . . ? F3 B2 F6 105.8(12) . . ? F4 B2 F6 99.3(11) . . ? F5 B2 F6 105.5(12) . . ? 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 N3 H3B F1 0.88 2.14 2.907(4) 145.9 . N3 H3B F1 0.88 2.38 3.097(5) 139.4 3_565 C1 H1A F2 0.95 2.52 3.036(6) 114.5 1_556 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.983 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.086 # Attachment 'c7.cif' data_c7 _database_code_depnum_ccdc_archive 'CCDC 761425' #TrackingRef 'c7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H42 Cl2 Fe N10 O8' _chemical_formula_weight 869.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe -1.1336 3.1974 '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 12.0681(6) _cell_length_b 16.8580(12) _cell_length_c 19.7972(9) _cell_angle_alpha 90.00 _cell_angle_beta 104.057(5) _cell_angle_gamma 90.00 _cell_volume 3907.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5279 _cell_measurement_theta_min 4.58 _cell_measurement_theta_max 70.95 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 4.905 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.34 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'ABSPACK(CrysAlis, Oxford Diffraction)' _exptl_special_details ; The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cobra. The data collection nominally covered over a hemisphere of Reciprocal space, by a combination of four sets of exposures with different \f angles for the crystal; each 10 s exposure covered 0.3\% in \w. The crystal-to-detector distance was 5.5 cm. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. Hydrogen atoms were added at calculated positions and refined using a riding model. Anisotropic displacement parameters were used for all non-H atoms; H-atoms were given isotropic displacement parameter equal to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic displacement parameter of the atom to which they are attached. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 10.2833 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% nil _diffrn_reflns_number 23664 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 71.10 _reflns_number_total 3773 _reflns_number_gt 2763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlis CCD, Oxford Diffraction Ltd' _computing_cell_refinement 'CrysAlis RED, Oxford Diffraction Ltd' _computing_data_reduction 'CrysAlis RED, Oxford Diffraction Ltd' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELXTL (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^)+(0.0586P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3773 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0966 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 0.901 _refine_ls_restrained_S_all 0.901 _refine_ls_shift/su_max 0.000 _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 1.0000 0.32937(3) 0.2500 0.01537(14) Uani 1 2 d S . . N1 N 0.84835(16) 0.33231(13) 0.26989(9) 0.0170(4) Uani 1 1 d . . . C1 C 0.7585(2) 0.28659(16) 0.24238(12) 0.0203(5) Uani 1 1 d . . . H1A H 0.7623 0.2522 0.2050 0.024 Uiso 1 1 calc R . . C2 C 0.6602(2) 0.28736(16) 0.26619(13) 0.0232(5) Uani 1 1 d . . . H2A H 0.5985 0.2532 0.2459 0.028 Uiso 1 1 calc R . . C3 C 0.6516(2) 0.33766(17) 0.31941(13) 0.0252(6) Uani 1 1 d . . . H3A H 0.5846 0.3388 0.3365 0.030 Uiso 1 1 calc R . . C4 C 0.7442(2) 0.38685(16) 0.34745(12) 0.0228(6) Uani 1 1 d . . . H4A H 0.7406 0.4231 0.3836 0.027 Uiso 1 1 calc R . . C5 C 0.8411(2) 0.38237(15) 0.32225(11) 0.0187(5) Uani 1 1 d . . . C6 C 0.9469(2) 0.42556(15) 0.35299(12) 0.0188(5) Uani 1 1 d . . . C7 C 0.9532(2) 0.48115(16) 0.41213(12) 0.0238(6) Uani 1 1 d . . . H7A H 1.0213 0.5146 0.4178 0.036 Uiso 1 1 calc R . . H7B H 0.9577 0.4508 0.4549 0.036 Uiso 1 1 calc R . . H7C H 0.8848 0.5147 0.4027 0.036 Uiso 1 1 calc R . . N2 N 1.03180(17) 0.40814(12) 0.32583(10) 0.0172(4) Uani 1 1 d . . . N3 N 1.13988(17) 0.43595(13) 0.36469(10) 0.0202(5) Uani 1 1 d . . . C8 C 1.1925(2) 0.38359(17) 0.42222(12) 0.0245(6) Uani 1 1 d . . . H8A H 1.2547 0.4117 0.4543 0.037 Uiso 1 1 calc R . . H8B H 1.2230 0.3365 0.4040 0.037 Uiso 1 1 calc R . . H8C H 1.1351 0.3674 0.4470 0.037 Uiso 1 1 calc R . . C9 C 1.2100(2) 0.47465(15) 0.32747(12) 0.0194(5) Uani 1 1 d . . . C10 C 1.3266(2) 0.46004(17) 0.34065(13) 0.0238(6) Uani 1 1 d . . . H10A H 1.3606 0.4207 0.3736 0.029 Uiso 1 1 calc R . . C11 C 1.3935(2) 0.50311(17) 0.30560(13) 0.0252(6) Uani 1 1 d . . . H11A H 1.4732 0.4931 0.3149 0.030 Uiso 1 1 calc R . . C12 C 1.3452(2) 0.56044(16) 0.25724(13) 0.0252(6) Uani 1 1 d . . . H12A H 1.3915 0.5891 0.2332 0.030 Uiso 1 1 calc R . . C13 C 1.2301(2) 0.57560(16) 0.24423(12) 0.0237(6) Uani 1 1 d . . . H13A H 1.1965 0.6146 0.2108 0.028 Uiso 1 1 calc R . . C14 C 1.1627(2) 0.53402(16) 0.27990(12) 0.0208(5) Uani 1 1 d . . . H14A H 1.0837 0.5461 0.2719 0.025 Uiso 1 1 calc R . . N4 N 1.04040(17) 0.24710(13) 0.32140(10) 0.0177(4) Uani 1 1 d . . . C15 C 1.0594(2) 0.20176(16) 0.36512(12) 0.0194(5) Uani 1 1 d . . . C16 C 1.0873(2) 0.14367(17) 0.42140(13) 0.0260(6) Uani 1 1 d . . . H16A H 1.1671 0.1271 0.4283 0.039 Uiso 1 1 calc R . . H16B H 1.0373 0.0974 0.4093 0.039 Uiso 1 1 calc R . . H16C H 1.0761 0.1675 0.4644 0.039 Uiso 1 1 calc R . . N5 N 0.6509(3) 0.45732(18) 0.48139(14) 0.0483(8) Uani 1 1 d . . . C17 C 0.6749(3) 0.4057(2) 0.51920(15) 0.0340(7) Uani 1 1 d . . . C18 C 0.7061(3) 0.33999(19) 0.56751(15) 0.0355(7) Uani 1 1 d . . . H18A H 0.6597 0.2935 0.5493 0.053 Uiso 1 1 calc R . . H18B H 0.6926 0.3548 0.6127 0.053 Uiso 1 1 calc R . . H18C H 0.7871 0.3273 0.5732 0.053 Uiso 1 1 calc R . . Cl10 Cl 0.45910(5) 0.21009(4) 0.42355(3) 0.02186(15) Uani 1 1 d . . . O11 O 0.46652(17) 0.29525(11) 0.42281(10) 0.0297(4) Uani 1 1 d . . . O12 O 0.34177(16) 0.18683(13) 0.41447(10) 0.0324(5) Uani 1 1 d . . . O13 O 0.52568(17) 0.18050(12) 0.48888(9) 0.0322(5) Uani 1 1 d . . . O14 O 0.50205(16) 0.17772(12) 0.36770(9) 0.0301(4) Uani 1 1 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 0.0180(3) 0.0185(3) 0.0098(2) 0.000 0.0038(2) 0.000 N1 0.0176(10) 0.0213(11) 0.0122(9) 0.0016(8) 0.0034(8) -0.0008(9) C1 0.0240(13) 0.0210(13) 0.0149(11) -0.0002(10) 0.0030(10) -0.0005(11) C2 0.0226(14) 0.0228(14) 0.0230(12) 0.0000(11) 0.0030(10) -0.0038(11) C3 0.0221(13) 0.0311(15) 0.0245(12) 0.0021(11) 0.0098(11) -0.0009(12) C4 0.0287(14) 0.0248(14) 0.0167(12) -0.0020(10) 0.0089(10) 0.0025(11) C5 0.0242(13) 0.0202(13) 0.0118(11) 0.0024(9) 0.0044(10) 0.0030(11) C6 0.0236(13) 0.0199(13) 0.0124(10) 0.0024(9) 0.0032(9) 0.0006(10) C7 0.0301(14) 0.0259(14) 0.0155(11) -0.0034(10) 0.0056(10) -0.0021(12) N2 0.0196(10) 0.0185(11) 0.0127(9) 0.0004(8) 0.0026(8) -0.0022(9) N3 0.0200(11) 0.0257(12) 0.0129(9) 0.0022(8) 0.0001(8) -0.0031(9) C8 0.0254(14) 0.0316(15) 0.0139(11) 0.0032(11) 0.0000(10) -0.0039(12) C9 0.0235(13) 0.0212(13) 0.0130(10) -0.0041(9) 0.0033(10) -0.0049(11) C10 0.0269(14) 0.0231(14) 0.0202(12) 0.0013(10) 0.0032(10) 0.0020(11) C11 0.0221(14) 0.0281(15) 0.0264(13) -0.0006(11) 0.0077(11) 0.0004(11) C12 0.0304(15) 0.0253(14) 0.0220(12) -0.0025(11) 0.0108(11) -0.0068(12) C13 0.0322(15) 0.0225(14) 0.0150(11) 0.0013(10) 0.0031(11) -0.0007(12) C14 0.0195(13) 0.0245(14) 0.0169(11) 0.0004(10) 0.0012(10) -0.0023(11) N4 0.0183(10) 0.0214(11) 0.0140(9) 0.0013(9) 0.0049(8) 0.0021(9) C15 0.0188(12) 0.0236(13) 0.0163(11) -0.0039(11) 0.0051(10) -0.0014(11) C16 0.0276(14) 0.0305(15) 0.0190(12) 0.0062(11) 0.0038(11) -0.0001(12) N5 0.082(2) 0.0360(16) 0.0341(14) -0.0056(13) 0.0286(15) -0.0047(16) C17 0.0417(18) 0.0373(18) 0.0284(15) -0.0118(14) 0.0191(13) -0.0080(14) C18 0.0307(16) 0.0406(19) 0.0339(15) -0.0055(14) 0.0054(12) -0.0009(14) Cl10 0.0233(3) 0.0244(3) 0.0175(3) 0.0029(2) 0.0043(2) 0.0000(3) O11 0.0414(12) 0.0192(10) 0.0291(9) 0.0022(8) 0.0099(8) 0.0004(9) O12 0.0255(10) 0.0429(13) 0.0287(10) 0.0020(9) 0.0063(8) -0.0028(9) O13 0.0336(11) 0.0364(12) 0.0222(9) 0.0081(9) -0.0018(8) -0.0014(9) O14 0.0319(11) 0.0347(11) 0.0251(9) -0.0016(9) 0.0095(8) 0.0026(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 Fe1 N4 1.956(2) 2_755 ? Fe1 N4 1.956(2) . ? Fe1 N1 1.9639(19) 2_755 ? Fe1 N1 1.9639(19) . ? Fe1 N2 1.971(2) . ? Fe1 N2 1.971(2) 2_755 ? N1 C1 1.334(3) . ? N1 C5 1.356(3) . ? C1 C2 1.378(4) . ? C1 H1A 0.9500 . ? C2 C3 1.376(4) . ? C2 H2A 0.9500 . ? C3 C4 1.393(4) . ? C3 H3A 0.9500 . ? C4 C5 1.381(3) . ? C4 H4A 0.9500 . ? C5 C6 1.467(4) . ? C6 N2 1.301(3) . ? C6 C7 1.487(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N2 N3 1.423(3) . ? N3 C9 1.409(3) . ? N3 C8 1.459(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.390(4) . ? C9 C14 1.397(4) . ? C10 C11 1.390(4) . ? C10 H10A 0.9500 . ? C11 C12 1.385(4) . ? C11 H11A 0.9500 . ? C12 C13 1.375(4) . ? C12 H12A 0.9500 . ? C13 C14 1.389(4) . ? C13 H13A 0.9500 . ? C14 H14A 0.9500 . ? N4 C15 1.135(3) . ? C15 C16 1.460(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N5 C17 1.139(4) . ? C17 C18 1.452(4) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? Cl10 O13 1.4361(19) . ? Cl10 O12 1.438(2) . ? Cl10 O14 1.4378(19) . ? Cl10 O11 1.4387(19) . ? 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 N4 Fe1 N4 89.66(12) 2_755 . ? N4 Fe1 N1 87.35(8) 2_755 2_755 ? N4 Fe1 N1 94.70(8) . 2_755 ? N4 Fe1 N1 94.70(8) 2_755 . ? N4 Fe1 N1 87.35(8) . . ? N1 Fe1 N1 177.11(13) 2_755 . ? N4 Fe1 N2 175.28(8) 2_755 . ? N4 Fe1 N2 87.65(8) . . ? N1 Fe1 N2 96.73(8) 2_755 . ? N1 Fe1 N2 81.30(8) . . ? N4 Fe1 N2 87.65(8) 2_755 2_755 ? N4 Fe1 N2 175.28(8) . 2_755 ? N1 Fe1 N2 81.30(8) 2_755 2_755 ? N1 Fe1 N2 96.73(8) . 2_755 ? N2 Fe1 N2 95.29(12) . 2_755 ? C1 N1 C5 118.3(2) . . ? C1 N1 Fe1 127.48(17) . . ? C5 N1 Fe1 113.89(16) . . ? N1 C1 C2 122.5(2) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C3 C2 C1 119.9(2) . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 118.0(2) . . ? C2 C3 H3A 121.0 . . ? C4 C3 H3A 121.0 . . ? C5 C4 C3 119.4(2) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? N1 C5 C4 121.8(2) . . ? N1 C5 C6 114.5(2) . . ? C4 C5 C6 123.5(2) . . ? N2 C6 C5 114.2(2) . . ? N2 C6 C7 124.9(2) . . ? C5 C6 C7 120.8(2) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 N2 N3 114.37(19) . . ? C6 N2 Fe1 116.08(17) . . ? N3 N2 Fe1 128.09(15) . . ? C9 N3 N2 117.22(18) . . ? C9 N3 C8 119.1(2) . . ? N2 N3 C8 113.0(2) . . ? N3 C8 H8A 109.5 . . ? N3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 118.8(2) . . ? C10 C9 N3 121.9(2) . . ? C14 C9 N3 119.1(2) . . ? C9 C10 C11 119.9(2) . . ? C9 C10 H10A 120.1 . . ? C11 C10 H10A 120.1 . . ? C12 C11 C10 120.8(3) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C13 C12 C11 119.7(2) . . ? C13 C12 H12A 120.2 . . ? C11 C12 H12A 120.2 . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13A 120.0 . . ? C14 C13 H13A 120.0 . . ? C13 C14 C9 120.7(2) . . ? C13 C14 H14A 119.6 . . ? C9 C14 H14A 119.6 . . ? C15 N4 Fe1 175.6(2) . . ? N4 C15 C16 178.4(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N5 C17 C18 179.7(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O13 Cl10 O12 109.67(12) . . ? O13 Cl10 O14 109.48(12) . . ? O12 Cl10 O14 109.17(12) . . ? O13 Cl10 O11 109.46(12) . . ? O12 Cl10 O11 109.43(12) . . ? O14 Cl10 O11 109.63(12) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 71.10 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.589 _refine_diff_density_min -0.403 _refine_diff_density_rms 0.068