# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Cl2 Fe N6 O2 S2, H2 O' _chemical_formula_sum 'C18 H19 Cl2 Fe N6 O3 S2' _chemical_formula_weight 558.26 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' 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' S S 0.1246 0.1234 '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 'C c' _symmetry_space_group_name_Hall 'C -2yc' 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' _cell_length_a 8.9480(18) _cell_length_b 22.429(5) _cell_length_c 11.469(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.28(3) _cell_angle_gamma 90.00 _cell_volume 2301.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 1.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9469 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11545 _diffrn_reflns_av_R_equivalents 0.1233 _diffrn_reflns_av_sigmaI/netI 0.1689 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4467 _reflns_number_gt 2063 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1144P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(5) _refine_ls_number_reflns 4467 _refine_ls_number_parameters 289 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1808 _refine_ls_R_factor_gt 0.0837 _refine_ls_wR_factor_ref 0.2389 _refine_ls_wR_factor_gt 0.1845 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 C15 C 0.9807(13) 0.6491(6) 0.5780(10) 0.053(3) Uani 1 1 d . . . C10 C 1.0276(15) 0.6468(6) 0.6957(11) 0.055(4) Uani 1 1 d . . . C11 C 1.1315(16) 0.6029(7) 0.7261(13) 0.069(4) Uani 1 1 d . . . H11A H 1.1691 0.6022 0.8024 0.083 Uiso 1 1 calc R . . C12 C 1.1810(17) 0.5610(7) 0.6502(14) 0.074(4) Uani 1 1 d . . . H12A H 1.2435 0.5303 0.6754 0.089 Uiso 1 1 calc R . . C13 C 1.1339(16) 0.5657(6) 0.5308(13) 0.062(4) Uani 1 1 d . . . C14 C 1.0367(17) 0.6077(6) 0.4991(12) 0.062(4) Uani 1 1 d . . . H14A H 1.0046 0.6097 0.4215 0.075 Uiso 1 1 calc R . . C16 C 0.8741(15) 0.6923(6) 0.5319(10) 0.050(3) Uani 1 1 d . . . H16A H 0.8502 0.6903 0.4527 0.060 Uiso 1 1 calc R . . C17 C 0.6280(14) 0.8121(6) 0.5779(10) 0.045(3) Uani 1 1 d . . . C6 C 0.9818(14) 0.8512(6) 0.9677(11) 0.050(3) Uani 1 1 d . . . C1 C 1.0277(15) 0.8511(6) 0.8513(12) 0.055(4) Uani 1 1 d . . . C2 C 1.1310(16) 0.8954(7) 0.8191(13) 0.074(4) Uani 1 1 d . . . H2A H 1.1645 0.8963 0.7429 0.089 Uiso 1 1 calc R . . C3 C 1.1824(18) 0.9365(7) 0.8962(12) 0.073(4) Uani 1 1 d . . . H3A H 1.2492 0.9654 0.8716 0.087 Uiso 1 1 calc R . . C4 C 1.1378(15) 0.9366(6) 1.0106(12) 0.060(4) Uani 1 1 d . . . C5 C 1.0366(16) 0.8940(6) 1.0456(11) 0.060(4) Uani 1 1 d . . . H5A H 1.0048 0.8938 1.1222 0.071 Uiso 1 1 calc R . . C7 C 0.8733(16) 0.8095(6) 1.0125(11) 0.054(3) Uani 1 1 d . . . H7A H 0.8475 0.8143 1.0900 0.065 Uiso 1 1 calc R . . C8 C 0.6347(14) 0.6916(6) 0.9675(11) 0.051(3) Uani 1 1 d . . . C18 C 0.4515(16) 0.8932(6) 0.5486(12) 0.069(4) Uani 1 1 d . . . H18A H 0.3987 0.9109 0.4835 0.103 Uiso 1 1 calc R . . H18B H 0.5143 0.9227 0.5856 0.103 Uiso 1 1 calc R . . H18C H 0.3811 0.8785 0.6036 0.103 Uiso 1 1 calc R . . C9 C 0.4518(15) 0.6087(7) 0.9913(12) 0.072(4) Uani 1 1 d . . . H9A H 0.3957 0.5929 1.0547 0.108 Uiso 1 1 calc R . . H9B H 0.5161 0.5782 0.9618 0.108 Uiso 1 1 calc R . . H9C H 0.3843 0.6217 0.9303 0.108 Uiso 1 1 calc R . . Cl2 Cl 1.2082(6) 0.5158(2) 0.4318(4) 0.0926(14) Uani 1 1 d . . . Cl1 Cl 1.2117(5) 0.9864(2) 1.1125(4) 0.0888(13) Uani 1 1 d . . . Fe1 Fe 0.83194(19) 0.74866(9) 0.77613(14) 0.0494(5) Uani 1 1 d . . . N4 N 0.8079(11) 0.7344(5) 0.5936(8) 0.048(3) Uani 1 1 d . . . N5 N 0.7086(11) 0.7691(5) 0.5272(8) 0.049(3) Uani 1 1 d . . . H5N H 0.6989 0.7629 0.4534 0.058 Uiso 1 1 calc R . . N6 N 0.5424(12) 0.8447(5) 0.5084(9) 0.055(3) Uani 1 1 d . . . H6A H 0.5405 0.8366 0.4351 0.066 Uiso 1 1 calc R . . N1 N 0.8081(11) 0.7661(5) 0.9556(9) 0.047(3) Uani 1 1 d . . . N2 N 0.7097(12) 0.7333(5) 1.0261(8) 0.052(3) Uani 1 1 d . . . N3 N 0.5409(12) 0.6584(5) 1.0320(9) 0.058(3) Uani 1 1 d . . . H3B H 0.5337 0.6679 1.1043 0.070 Uiso 1 1 calc R . . O2 O 0.9847(10) 0.6875(4) 0.7735(7) 0.059(2) Uani 1 1 d . . . O1 O 0.9838(10) 0.8089(4) 0.7775(7) 0.062(3) Uani 1 1 d . . . O1W O 0.7940(10) 0.7535(6) 0.2892(7) 0.079(3) Uani 1 1 d . . . H2W H 0.8790 0.7679 0.3088 0.119 Uiso 1 1 d R . . H1W H 0.7293 0.7814 0.2866 0.119 Uiso 1 1 d R . . S2 S 0.6454(4) 0.82484(18) 0.7243(3) 0.0662(11) Uani 1 1 d . . . S1 S 0.6473(4) 0.67551(19) 0.8204(3) 0.0664(11) 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 C15 0.047(8) 0.079(9) 0.033(6) 0.001(6) 0.013(5) 0.007(7) C10 0.070(9) 0.061(9) 0.035(7) -0.003(6) 0.009(6) 0.014(8) C11 0.067(10) 0.085(11) 0.054(9) -0.003(8) 0.003(7) 0.023(9) C12 0.080(11) 0.068(11) 0.076(11) 0.009(8) 0.021(8) 0.009(8) C13 0.067(10) 0.063(9) 0.058(9) 0.000(7) 0.020(8) 0.007(8) C14 0.071(10) 0.065(10) 0.052(9) -0.006(7) 0.014(7) 0.003(8) C16 0.056(8) 0.073(9) 0.021(6) -0.001(6) 0.002(5) 0.001(7) C17 0.042(8) 0.060(9) 0.033(7) -0.005(6) 0.002(5) 0.002(7) C6 0.059(9) 0.050(8) 0.042(7) 0.006(6) 0.003(6) -0.011(7) C1 0.054(9) 0.061(9) 0.050(8) 0.002(7) -0.008(6) -0.007(7) C2 0.079(11) 0.102(12) 0.042(8) 0.002(9) 0.019(7) -0.016(10) C3 0.086(11) 0.083(11) 0.050(9) 0.001(8) 0.008(7) -0.037(9) C4 0.057(9) 0.064(9) 0.058(9) 0.004(7) -0.013(7) -0.012(7) C5 0.077(11) 0.066(9) 0.035(8) -0.007(7) -0.002(6) 0.005(8) C7 0.060(9) 0.065(9) 0.037(7) -0.010(7) -0.006(6) 0.004(8) C8 0.043(8) 0.064(9) 0.045(8) 0.003(7) 0.005(6) 0.003(7) C18 0.075(10) 0.074(10) 0.057(10) -0.003(7) -0.002(7) 0.018(9) C9 0.053(9) 0.095(12) 0.069(11) 0.018(8) -0.001(7) -0.019(9) Cl2 0.119(4) 0.082(3) 0.078(3) -0.013(2) 0.017(2) 0.025(3) Cl1 0.112(4) 0.084(3) 0.070(3) -0.015(2) -0.001(2) -0.026(3) Fe1 0.0541(9) 0.0769(11) 0.0174(7) -0.0034(8) 0.0038(6) -0.0005(11) N4 0.037(6) 0.080(9) 0.028(5) 0.006(5) 0.007(5) -0.006(6) N5 0.042(6) 0.075(8) 0.029(5) 0.001(5) -0.006(5) 0.000(5) N6 0.063(8) 0.069(7) 0.034(6) 0.005(5) -0.002(5) 0.001(6) N1 0.041(6) 0.069(8) 0.031(5) 0.006(5) 0.004(5) 0.001(6) N2 0.051(6) 0.068(8) 0.038(5) -0.002(5) 0.006(5) -0.004(6) N3 0.064(8) 0.068(7) 0.044(6) -0.005(6) 0.014(6) -0.009(6) O2 0.069(6) 0.081(7) 0.028(5) 0.009(4) 0.000(4) 0.006(5) O1 0.068(6) 0.092(7) 0.026(4) -0.010(4) 0.018(4) -0.005(5) O1W 0.057(7) 0.147(9) 0.034(5) 0.010(6) -0.001(5) 0.008(6) S2 0.076(3) 0.096(3) 0.0265(19) -0.0093(19) 0.0001(16) 0.021(2) S1 0.072(3) 0.099(3) 0.0285(19) -0.0121(19) 0.0073(16) -0.017(2) _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 C15 C14 1.397(17) . ? C15 C10 1.406(17) . ? C15 C16 1.450(18) . ? C10 O2 1.339(15) . ? C10 C11 1.393(18) . ? C11 C12 1.36(2) . ? C11 H11A 0.9300 . ? C12 C13 1.43(2) . ? C12 H12A 0.9300 . ? C13 C14 1.327(18) . ? C13 Cl2 1.738(14) . ? C14 H14A 0.9300 . ? C16 N4 1.328(16) . ? C16 H16A 0.9300 . ? C17 N6 1.314(15) . ? C17 N5 1.345(16) . ? C17 S2 1.707(12) . ? C6 C5 1.393(17) . ? C6 C1 1.405(17) . ? C6 C7 1.449(18) . ? C1 O1 1.323(15) . ? C1 C2 1.41(2) . ? C2 C3 1.351(19) . ? C2 H2A 0.9300 . ? C3 C4 1.379(18) . ? C3 H3A 0.9300 . ? C4 C5 1.383(18) . ? C4 Cl1 1.737(14) . ? C5 H5A 0.9300 . ? C7 N1 1.304(16) . ? C7 H7A 0.9300 . ? C8 N2 1.326(16) . ? C8 N3 1.354(16) . ? C8 S1 1.731(13) . ? C18 N6 1.442(16) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C9 N3 1.443(17) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? Fe1 O1 1.917(10) . ? Fe1 O2 1.937(9) . ? Fe1 N1 2.111(10) . ? Fe1 N4 2.124(10) . ? Fe1 S1 2.391(4) . ? Fe1 S2 2.453(4) . ? N4 N5 1.394(14) . ? N5 H5N 0.8600 . ? N6 H6A 0.8600 . ? N1 N2 1.415(14) . ? N3 H3B 0.8600 . ? O1W H2W 0.8517 . ? O1W H1W 0.8513 . ? 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 C14 C15 C10 119.6(12) . . ? C14 C15 C16 116.7(12) . . ? C10 C15 C16 123.7(11) . . ? O2 C10 C11 121.0(12) . . ? O2 C10 C15 122.1(12) . . ? C11 C10 C15 116.7(12) . . ? C12 C11 C10 123.5(15) . . ? C12 C11 H11A 118.2 . . ? C10 C11 H11A 118.2 . . ? C11 C12 C13 118.0(14) . . ? C11 C12 H12A 121.0 . . ? C13 C12 H12A 121.0 . . ? C14 C13 C12 119.5(13) . . ? C14 C13 Cl2 122.5(12) . . ? C12 C13 Cl2 118.1(11) . . ? C13 C14 C15 122.4(13) . . ? C13 C14 H14A 118.8 . . ? C15 C14 H14A 118.8 . . ? N4 C16 C15 125.3(11) . . ? N4 C16 H16A 117.3 . . ? C15 C16 H16A 117.3 . . ? N6 C17 N5 116.6(11) . . ? N6 C17 S2 122.9(10) . . ? N5 C17 S2 120.5(10) . . ? C5 C6 C1 120.3(12) . . ? C5 C6 C7 116.5(12) . . ? C1 C6 C7 123.2(12) . . ? O1 C1 C6 121.4(12) . . ? O1 C1 C2 121.5(13) . . ? C6 C1 C2 117.0(13) . . ? C3 C2 C1 121.6(14) . . ? C3 C2 H2A 119.2 . . ? C1 C2 H2A 119.2 . . ? C2 C3 C4 121.5(13) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C3 C4 C5 118.7(12) . . ? C3 C4 Cl1 121.8(11) . . ? C5 C4 Cl1 119.4(11) . . ? C4 C5 C6 120.9(12) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? N1 C7 C6 126.9(13) . . ? N1 C7 H7A 116.6 . . ? C6 C7 H7A 116.6 . . ? N2 C8 N3 115.1(12) . . ? N2 C8 S1 126.7(10) . . ? N3 C8 S1 118.2(10) . . ? N6 C18 H18A 109.5 . . ? N6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O1 Fe1 O2 90.0(4) . . ? O1 Fe1 N1 87.1(4) . . ? O2 Fe1 N1 103.5(4) . . ? O1 Fe1 N4 99.8(4) . . ? O2 Fe1 N4 86.2(4) . . ? N1 Fe1 N4 168.2(4) . . ? O1 Fe1 S1 167.3(2) . . ? O2 Fe1 S1 90.5(3) . . ? N1 Fe1 S1 80.5(3) . . ? N4 Fe1 S1 92.9(3) . . ? O1 Fe1 S2 89.4(3) . . ? O2 Fe1 S2 165.1(2) . . ? N1 Fe1 S2 91.4(3) . . ? N4 Fe1 S2 79.2(3) . . ? S1 Fe1 S2 93.41(15) . . ? C16 N4 N5 113.1(11) . . ? C16 N4 Fe1 126.6(9) . . ? N5 N4 Fe1 120.2(8) . . ? C17 N5 N4 120.4(10) . . ? C17 N5 H5N 119.8 . . ? N4 N5 H5N 119.8 . . ? C17 N6 C18 123.4(11) . . ? C17 N6 H6A 118.3 . . ? C18 N6 H6A 118.3 . . ? C7 N1 N2 112.3(11) . . ? C7 N1 Fe1 124.9(9) . . ? N2 N1 Fe1 122.6(8) . . ? C8 N2 N1 113.0(10) . . ? C8 N3 C9 126.4(11) . . ? C8 N3 H3B 116.8 . . ? C9 N3 H3B 116.8 . . ? C10 O2 Fe1 134.9(8) . . ? C1 O1 Fe1 135.2(8) . . ? H2W O1W H1W 109.5 . . ? C17 S2 Fe1 99.7(4) . . ? C8 S1 Fe1 97.1(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.509 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.130 _database_code_depnum_ccdc_archive 'CCDC 936360' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Cl2 Fe N6 O2 S2, H2 O' _chemical_formula_sum 'C18 H19 Cl2 Fe N6 O3 S2' _chemical_formula_weight 558.26 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' 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' S S 0.1246 0.1234 '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 'C c' _symmetry_space_group_name_Hall 'C -2yc' 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' _cell_length_a 8.9606(18) _cell_length_b 22.354(5) _cell_length_c 11.337(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.20(3) _cell_angle_gamma 90.00 _cell_volume 2270.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 260(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 1.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9462 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 260(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23294 _diffrn_reflns_av_R_equivalents 0.1158 _diffrn_reflns_av_sigmaI/netI 0.1064 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4436 _reflns_number_gt 2593 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0169P)^2^+19.5036P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(5) _refine_ls_number_reflns 4436 _refine_ls_number_parameters 299 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1574 _refine_ls_R_factor_gt 0.0786 _refine_ls_wR_factor_ref 0.1743 _refine_ls_wR_factor_gt 0.1342 _refine_ls_goodness_of_fit_ref 1.129 _refine_ls_restrained_S_all 1.129 _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 C1 C 0.6764(14) 0.6496(5) 0.5484(10) 0.055(3) Uani 1 1 d . . . C2 C 0.5784(17) 0.6061(6) 0.5827(14) 0.082(5) Uani 1 1 d . . . H21 H 0.5484 0.6049 0.6607 0.098 Uiso 1 1 calc R . . C3 C 0.5239(17) 0.5644(6) 0.5050(12) 0.077(4) Uani 1 1 d . . . H3A H 0.4575 0.5353 0.5304 0.092 Uiso 1 1 calc R . . C4 C 0.5666(14) 0.5652(5) 0.3905(10) 0.054(3) Uani 1 1 d . . . C5 C 0.6649(13) 0.6076(5) 0.3534(10) 0.048(3) Uani 1 1 d . . . H5A H 0.6945 0.6076 0.2752 0.058 Uiso 1 1 calc R . . C6 C 0.7215(12) 0.6509(5) 0.4307(9) 0.046(3) Uani 1 1 d . . . C7 C 0.8305(13) 0.6938(5) 0.3848(9) 0.044(3) Uani 1 1 d . . . H7A H 0.8540 0.6901 0.3056 0.053 Uiso 1 1 calc R . . C8 C 1.0685(12) 0.8084(5) 0.4299(8) 0.040(3) Uani 1 1 d . . . C9 C 1.2544(14) 0.8904(5) 0.4106(10) 0.061(3) Uani 1 1 d . . . H9A H 1.3225 0.8765 0.4711 0.092 Uiso 1 1 calc R . . H9B H 1.1908 0.9207 0.4423 0.092 Uiso 1 1 calc R . . H9C H 1.3097 0.9069 0.3466 0.092 Uiso 1 1 calc R . . C10 C 0.6796(15) 0.8509(5) 0.6840(11) 0.057(3) Uani 1 1 d . . . C11 C 0.5795(18) 0.8970(7) 0.6498(13) 0.087(5) Uani 1 1 d . . . H11A H 0.5500 0.8995 0.5708 0.105 Uiso 1 1 calc R . . C12 C 0.5243(17) 0.9378(6) 0.7260(13) 0.081(4) Uani 1 1 d . . . H12A H 0.4577 0.9671 0.7002 0.097 Uiso 1 1 calc R . . C13 C 0.5695(13) 0.9345(5) 0.8424(11) 0.055(3) Uani 1 1 d . . . C14 C 0.6659(13) 0.8912(5) 0.8814(11) 0.053(3) Uani 1 1 d . . . H14A H 0.6946 0.8895 0.9606 0.064 Uiso 1 1 calc R . . C15 C 0.7216(12) 0.8493(5) 0.8014(9) 0.045(3) Uani 1 1 d . . . C16 C 0.8279(14) 0.8070(5) 0.8493(10) 0.047(3) Uani 1 1 d . . . H16A H 0.8506 0.8094 0.9296 0.057 Uiso 1 1 calc R . . C17 C 1.0724(12) 0.6881(5) 0.8044(9) 0.045(3) Uani 1 1 d . . . C18 C 1.2597(15) 0.6085(5) 0.8286(10) 0.067(4) Uani 1 1 d . . . H18A H 1.3130 0.6220 0.7610 0.100 Uiso 1 1 calc R . . H18B H 1.1985 0.5749 0.8071 0.100 Uiso 1 1 calc R . . H18C H 1.3295 0.5970 0.8898 0.100 Uiso 1 1 calc R . . Cl1 Cl 0.4920(5) 0.51441(15) 0.2882(3) 0.0813(11) Uani 1 1 d . . . Cl2 Cl 0.4963(5) 0.98427(15) 0.9433(4) 0.0848(11) Uani 1 1 d . . . Fe1 Fe 0.8773(2) 0.75074(8) 0.61487(16) 0.0473(4) Uani 1 1 d . . . H1W H 0.820(3) 0.741(8) 0.103(15) 0.11(7) Uiso 1 1 d D . . H2W H 0.944(19) 0.771(12) 0.15(2) 0.32(18) Uiso 1 1 d D . . N1 N 0.8956(10) 0.7353(4) 0.4421(7) 0.039(2) Uani 1 1 d . . . N2 N 0.9919(10) 0.7684(4) 0.3713(7) 0.041(2) Uani 1 1 d . . . N3 N 1.1657(11) 0.8416(4) 0.3684(9) 0.057(3) Uani 1 1 d . . . H3B H 1.1753 0.8323 0.2954 0.069 Uiso 1 1 calc R . . N4 N 0.8940(10) 0.7659(4) 0.7899(8) 0.042(2) Uani 1 1 d . . . N5 N 0.9917(10) 0.7301(4) 0.8581(7) 0.045(2) Uani 1 1 d . . . H5N H 0.9995 0.7351 0.9332 0.054 Uiso 1 1 calc R . . N6 N 1.1665(12) 0.6563(4) 0.8706(9) 0.058(3) Uani 1 1 d . . . H6A H 1.1726 0.6648 0.9445 0.069 Uiso 1 1 calc R . . O1 O 0.7256(10) 0.6911(4) 0.6263(7) 0.068(3) Uani 1 1 d . . . O2 O 0.7251(11) 0.8123(4) 0.6034(8) 0.069(3) Uani 1 1 d . . . O1W O 0.9142(12) 0.7459(6) 0.0984(8) 0.074(3) Uani 1 1 d D . . S1 S 1.0574(4) 0.82201(16) 0.5798(3) 0.0578(9) Uani 1 1 d . . . S2 S 1.0571(4) 0.67741(16) 0.6559(3) 0.0592(9) 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 C1 0.065(9) 0.049(8) 0.051(7) 0.002(6) 0.020(6) 0.001(6) C2 0.106(12) 0.061(9) 0.081(9) -0.002(8) 0.055(9) -0.024(8) C3 0.096(11) 0.064(9) 0.071(9) -0.004(7) 0.035(8) -0.018(8) C4 0.069(9) 0.038(6) 0.056(8) 0.005(5) 0.000(6) -0.006(6) C5 0.061(9) 0.041(6) 0.042(6) -0.002(5) -0.002(6) 0.009(6) C6 0.040(7) 0.042(6) 0.055(7) 0.015(5) 0.004(5) 0.002(5) C7 0.056(8) 0.050(7) 0.027(6) 0.009(5) 0.001(5) 0.006(6) C8 0.057(8) 0.037(6) 0.027(5) 0.004(4) 0.014(5) -0.002(5) C9 0.069(9) 0.042(7) 0.073(8) 0.001(6) 0.014(7) -0.013(7) C10 0.071(9) 0.045(7) 0.056(8) -0.007(6) -0.017(6) -0.008(7) C11 0.118(13) 0.074(10) 0.068(9) 0.003(8) -0.043(9) 0.026(10) C12 0.106(12) 0.047(8) 0.088(11) 0.006(8) -0.029(9) 0.016(8) C13 0.044(8) 0.048(7) 0.073(9) 0.004(6) 0.013(6) 0.004(6) C14 0.055(8) 0.053(7) 0.051(7) 0.007(6) -0.004(6) -0.009(6) C15 0.051(8) 0.042(6) 0.041(6) 0.003(5) -0.011(5) 0.002(5) C16 0.058(8) 0.042(7) 0.043(6) -0.004(5) 0.001(5) 0.002(6) C17 0.049(8) 0.038(7) 0.049(7) 0.004(5) -0.016(5) -0.010(6) C18 0.085(10) 0.044(7) 0.070(9) -0.013(6) -0.018(7) 0.015(7) Cl1 0.111(3) 0.056(2) 0.077(2) -0.0044(17) -0.0015(19) -0.020(2) Cl2 0.101(3) 0.053(2) 0.100(3) -0.0067(19) 0.004(2) 0.017(2) Fe1 0.0752(10) 0.0426(8) 0.0243(6) -0.0033(6) 0.0027(6) -0.0017(9) N1 0.049(6) 0.030(6) 0.039(5) 0.000(4) 0.013(4) 0.004(4) N2 0.049(6) 0.043(5) 0.031(4) 0.008(4) 0.010(4) -0.001(4) N3 0.068(8) 0.058(6) 0.046(5) 0.005(5) 0.022(5) 0.002(5) N4 0.041(6) 0.042(6) 0.041(6) 0.004(4) -0.016(4) -0.004(4) N5 0.055(6) 0.044(5) 0.035(4) 0.004(4) -0.006(4) 0.004(4) N6 0.077(8) 0.052(6) 0.043(5) -0.001(5) -0.021(5) -0.002(6) O1 0.088(7) 0.068(7) 0.049(5) -0.010(4) 0.038(5) -0.014(5) O2 0.088(7) 0.062(6) 0.056(5) -0.001(5) -0.030(5) 0.010(5) O1W 0.076(8) 0.105(8) 0.041(5) 0.017(5) -0.002(5) -0.002(7) S1 0.073(2) 0.058(2) 0.0426(18) -0.0143(16) 0.0176(15) -0.0166(18) S2 0.077(2) 0.060(2) 0.0394(17) -0.0104(16) -0.0149(15) 0.0198(19) _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 C1 O1 1.349(14) . ? C1 C6 1.402(14) . ? C1 C2 1.373(17) . ? C2 C3 1.365(19) . ? C2 H21 0.9300 . ? C3 C4 1.361(15) . ? C3 H3A 0.9300 . ? C4 C5 1.366(15) . ? C4 Cl1 1.746(12) . ? C5 C6 1.394(14) . ? C5 H5A 0.9300 . ? C6 C7 1.472(15) . ? C7 N1 1.268(13) . ? C7 H7A 0.9300 . ? C8 N2 1.300(13) . ? C8 N3 1.350(13) . ? C8 S1 1.732(9) . ? C9 N3 1.426(13) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O2 1.327(14) . ? C10 C15 1.376(14) . ? C10 C11 1.416(18) . ? C11 C12 1.356(19) . ? C11 H11A 0.9300 . ? C12 C13 1.375(16) . ? C12 H12A 0.9300 . ? C13 C14 1.364(15) . ? C13 Cl2 1.734(12) . ? C14 C15 1.402(15) . ? C14 H14A 0.9300 . ? C15 C16 1.441(14) . ? C16 N4 1.290(13) . ? C16 H16A 0.9300 . ? C17 N6 1.324(13) . ? C17 N5 1.338(14) . ? C17 S2 1.703(11) . ? C18 N6 1.443(14) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? Fe1 O1 1.910(9) . ? Fe1 O2 1.940(9) . ? Fe1 N1 1.999(9) . ? Fe1 N4 2.016(9) . ? Fe1 S1 2.308(4) . ? Fe1 S2 2.338(4) . ? N1 N2 1.402(11) . ? N3 H3B 0.8600 . ? N4 N5 1.406(11) . ? N5 H5N 0.8600 . ? N6 H6A 0.8600 . ? O1W H1W 0.851(10) . ? O1W H2W 0.850(10) . ? 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 O1 C1 C6 120.9(10) . . ? O1 C1 C2 120.3(11) . . ? C6 C1 C2 118.8(12) . . ? C3 C2 C1 121.6(13) . . ? C3 C2 H21 119.2 . . ? C1 C2 H21 119.2 . . ? C2 C3 C4 120.1(13) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C3 C4 C5 120.0(11) . . ? C3 C4 Cl1 120.9(10) . . ? C5 C4 Cl1 119.1(9) . . ? C4 C5 C6 121.0(11) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 118.5(10) . . ? C1 C6 C7 123.8(10) . . ? C5 C6 C7 117.7(10) . . ? N1 C7 C6 126.7(10) . . ? N1 C7 H7A 116.7 . . ? C6 C7 H7A 116.7 . . ? N2 C8 N3 117.0(9) . . ? N2 C8 S1 125.6(8) . . ? N3 C8 S1 117.4(9) . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C15 124.6(11) . . ? O2 C10 C11 119.1(11) . . ? C15 C10 C11 116.2(12) . . ? C12 C11 C10 123.5(13) . . ? C12 C11 H11A 118.3 . . ? C10 C11 H11A 118.3 . . ? C11 C12 C13 118.2(13) . . ? C11 C12 H12A 120.9 . . ? C13 C12 H12A 120.9 . . ? C12 C13 C14 121.4(12) . . ? C12 C13 Cl2 119.4(10) . . ? C14 C13 Cl2 119.1(10) . . ? C13 C14 C15 119.7(11) . . ? C13 C14 H14A 120.2 . . ? C15 C14 H14A 120.2 . . ? C10 C15 C14 121.0(11) . . ? C10 C15 C16 123.1(11) . . ? C14 C15 C16 115.9(9) . . ? N4 C16 C15 125.3(11) . . ? N4 C16 H16A 117.3 . . ? C15 C16 H16A 117.3 . . ? N6 C17 N5 117.5(10) . . ? N6 C17 S2 121.4(10) . . ? N5 C17 S2 121.0(8) . . ? N6 C18 H18A 109.5 . . ? N6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 Fe1 O2 89.9(4) . . ? O1 Fe1 N1 91.1(4) . . ? O2 Fe1 N1 97.4(4) . . ? O1 Fe1 N4 95.1(4) . . ? O2 Fe1 N4 89.1(4) . . ? N1 Fe1 N4 171.0(4) . . ? O1 Fe1 S1 174.0(3) . . ? O2 Fe1 S1 89.5(3) . . ? N1 Fe1 S1 83.0(3) . . ? N4 Fe1 S1 90.9(3) . . ? O1 Fe1 S2 89.2(3) . . ? O2 Fe1 S2 172.4(3) . . ? N1 Fe1 S2 90.2(3) . . ? N4 Fe1 S2 83.4(3) . . ? S1 Fe1 S2 92.12(15) . . ? C7 N1 N2 112.0(9) . . ? C7 N1 Fe1 125.6(8) . . ? N2 N1 Fe1 122.3(7) . . ? C8 N2 N1 113.2(8) . . ? C8 N3 C9 127.6(10) . . ? C8 N3 H3B 116.2 . . ? C9 N3 H3B 116.2 . . ? C16 N4 N5 114.0(9) . . ? C16 N4 Fe1 127.4(8) . . ? N5 N4 Fe1 118.5(7) . . ? C17 N5 N4 119.0(9) . . ? C17 N5 H5N 120.5 . . ? N4 N5 H5N 120.5 . . ? C17 N6 C18 125.2(10) . . ? C17 N6 H6A 117.4 . . ? C18 N6 H6A 117.4 . . ? C1 O1 Fe1 131.2(7) . . ? C10 O2 Fe1 129.8(8) . . ? H1W O1W H2W 109.6(19) . . ? C8 S1 Fe1 95.9(4) . . ? C17 S2 Fe1 98.0(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.605 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 936361' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H17 Cl2 Fe N6 O2 S2, H2 O' _chemical_formula_sum 'C18 H19 Cl2 Fe N6 O3 S2' _chemical_formula_weight 558.26 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' 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' S S 0.1246 0.1234 '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 'C c' _symmetry_space_group_name_Hall 'C -2yc' 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' _cell_length_a 8.9434(18) _cell_length_b 22.298(5) _cell_length_c 11.270(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.301(3) _cell_angle_gamma 90.00 _cell_volume 2247.0(8) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.650 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 1.129 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9457 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11274 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0597 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4385 _reflns_number_gt 3808 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0742P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(2) _refine_ls_number_reflns 4385 _refine_ls_number_parameters 291 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 C1 C 0.4115(5) 0.3484(2) 0.8802(4) 0.0161(10) Uani 1 1 d . . . C2 C 0.5096(6) 0.3940(2) 0.8437(5) 0.0237(11) Uani 1 1 d . . . H2A H 0.5357 0.3960 0.7626 0.028 Uiso 1 1 calc R . . C3 C 0.5693(6) 0.4359(2) 0.9221(4) 0.0261(12) Uani 1 1 d . . . H3A H 0.6364 0.4658 0.8955 0.031 Uiso 1 1 calc R . . C4 C 0.5291(6) 0.4335(2) 1.0404(4) 0.0214(11) Uani 1 1 d . . . C5 C 0.4295(5) 0.3914(2) 1.0788(5) 0.0191(10) Uani 1 1 d . . . H5A H 0.4004 0.3915 1.1593 0.023 Uiso 1 1 calc R . . C6 C 0.3702(5) 0.3482(2) 1.0006(4) 0.0162(10) Uani 1 1 d . . . C7 C 0.2660(6) 0.3055(2) 1.0500(4) 0.0178(10) Uani 1 1 d . . . H7A H 0.2468 0.3087 1.1323 0.021 Uiso 1 1 calc R . . C8 C 0.0195(5) 0.1912(2) 1.0039(4) 0.0168(10) Uani 1 1 d . . . C9 C -0.1670(6) 0.1103(2) 1.0167(5) 0.0250(11) Uani 1 1 d . . . H9A H -0.2198 0.1238 0.9444 0.038 Uiso 1 1 calc R . . H9B H -0.2399 0.0974 1.0751 0.038 Uiso 1 1 calc R . . H9C H -0.1014 0.0766 0.9977 0.038 Uiso 1 1 calc R . . C10 C 0.4065(5) 0.1492(2) 0.7662(4) 0.0169(10) Uani 1 1 d . . . C11 C 0.5027(6) 0.1029(2) 0.8046(5) 0.0238(11) Uani 1 1 d . . . H11A H 0.5267 0.0994 0.8869 0.029 Uiso 1 1 calc R . . C12 C 0.5635(6) 0.0622(2) 0.7262(4) 0.0268(12) Uani 1 1 d . . . H12A H 0.6301 0.0319 0.7542 0.032 Uiso 1 1 calc R . . C13 C 0.5258(6) 0.0663(2) 0.6058(4) 0.0202(10) Uani 1 1 d . . . C14 C 0.4274(5) 0.1096(2) 0.5652(5) 0.0187(10) Uani 1 1 d . . . H14A H 0.3992 0.1110 0.4835 0.022 Uiso 1 1 calc R . . C15 C 0.3687(5) 0.1517(2) 0.6445(4) 0.0168(10) Uani 1 1 d . . . C16 C 0.2663(5) 0.1946(2) 0.5931(4) 0.0163(10) Uani 1 1 d . . . H16A H 0.2478 0.1929 0.5098 0.020 Uiso 1 1 calc R . . C17 C 0.0167(5) 0.3121(2) 0.6406(4) 0.0164(10) Uani 1 1 d . . . C18 C -0.1712(6) 0.3913(2) 0.6212(5) 0.0255(11) Uani 1 1 d . . . H18A H -0.2325 0.3751 0.6847 0.038 Uiso 1 1 calc R . . H18B H -0.2365 0.4072 0.5576 0.038 Uiso 1 1 calc R . . H18C H -0.1076 0.4236 0.6530 0.038 Uiso 1 1 calc R . . Cl1 Cl 0.60282(16) 0.48573(6) 1.14097(12) 0.0298(3) Uani 1 1 d . . . Cl2 Cl 0.60001(16) 0.01562(6) 0.50581(12) 0.0300(3) Uani 1 1 d . . . Fe1 Fe 0.20723(8) 0.24936(3) 0.82294(7) 0.01463(16) Uani 1 1 d . . . N1 N 0.1975(4) 0.2636(2) 0.9918(4) 0.0149(9) Uani 1 1 d . . . N2 N 0.1012(4) 0.23027(19) 1.0641(3) 0.0163(8) Uani 1 1 d . . . N3 N -0.0790(5) 0.15872(18) 1.0650(4) 0.0198(9) Uani 1 1 d . . . H3B H -0.0904 0.1678 1.1402 0.024 Uiso 1 1 calc R . . N4 N 0.1977(4) 0.2355(2) 0.6523(4) 0.0155(9) Uani 1 1 d . . . N5 N 0.0988(4) 0.27126(19) 0.5851(3) 0.0154(8) Uani 1 1 d . . . H5N H 0.0910 0.2669 0.5076 0.018 Uiso 1 1 calc R . . N6 N -0.0780(4) 0.34406(17) 0.5743(4) 0.0177(9) Uani 1 1 d . . . H6A H -0.0848 0.3362 0.4979 0.021 Uiso 1 1 calc R . . O1 O 0.3630(4) 0.30856(16) 0.8007(3) 0.0197(8) Uani 1 1 d . . . O2 O 0.3588(4) 0.18846(16) 0.8465(3) 0.0188(8) Uani 1 1 d . . . O1W O 0.1724(4) 0.25486(19) 0.3421(3) 0.0290(9) Uani 1 1 d D . . H2W H 0.2667 0.2548 0.3336 0.044 Uiso 1 1 d RD . . H1W H 0.1208 0.2415 0.2839 0.044 Uiso 1 1 d RD . . S1 S 0.02995(13) 0.18016(6) 0.85039(11) 0.0187(3) Uani 1 1 d . . . S2 S 0.03417(14) 0.32157(6) 0.79101(11) 0.0192(3) 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 C1 0.017(2) 0.020(3) 0.011(2) -0.0001(19) -0.0014(18) 0.0024(19) C2 0.026(3) 0.032(3) 0.013(2) -0.002(2) 0.004(2) -0.003(2) C3 0.032(3) 0.025(3) 0.021(3) 0.002(2) 0.004(2) -0.009(2) C4 0.027(3) 0.020(3) 0.018(3) -0.001(2) -0.002(2) -0.002(2) C5 0.021(3) 0.022(2) 0.014(2) 0.001(2) -0.003(2) 0.000(2) C6 0.020(2) 0.019(2) 0.010(2) 0.0041(18) 0.0007(18) 0.0010(19) C7 0.023(3) 0.021(3) 0.010(2) -0.0002(18) 0.0026(19) 0.002(2) C8 0.020(3) 0.021(3) 0.010(2) -0.0009(19) 0.0020(18) 0.002(2) C9 0.029(3) 0.024(3) 0.022(3) -0.004(2) 0.004(2) -0.007(2) C10 0.018(2) 0.018(3) 0.014(2) 0.0002(19) 0.0052(18) -0.002(2) C11 0.031(3) 0.025(3) 0.015(2) 0.001(2) -0.001(2) 0.004(2) C12 0.035(3) 0.027(3) 0.018(3) 0.000(2) -0.001(2) 0.012(2) C13 0.025(3) 0.018(2) 0.018(3) -0.002(2) 0.008(2) 0.002(2) C14 0.020(3) 0.024(3) 0.012(2) 0.000(2) 0.004(2) -0.002(2) C15 0.018(2) 0.019(2) 0.014(2) 0.0005(18) 0.0017(18) -0.0004(19) C16 0.019(2) 0.021(3) 0.009(2) -0.0010(18) 0.0028(18) -0.002(2) C17 0.020(3) 0.020(3) 0.009(2) -0.0003(19) 0.0009(18) -0.003(2) C18 0.026(3) 0.025(3) 0.025(3) -0.002(2) -0.001(2) 0.007(2) Cl1 0.0430(8) 0.0261(7) 0.0203(7) -0.0059(5) 0.0005(6) -0.0123(6) Cl2 0.0433(8) 0.0250(7) 0.0219(7) -0.0067(5) 0.0033(6) 0.0117(6) Fe1 0.0184(3) 0.0194(3) 0.0062(3) -0.0002(2) 0.0016(2) 0.0003(3) N1 0.015(2) 0.017(2) 0.013(2) 0.0019(17) 0.0023(16) 0.0009(17) N2 0.019(2) 0.020(2) 0.0101(19) 0.0011(16) 0.0020(15) -0.0034(17) N3 0.023(2) 0.022(2) 0.014(2) -0.0039(18) 0.0033(17) -0.0037(17) N4 0.018(2) 0.017(2) 0.011(2) 0.0034(17) -0.0023(17) -0.0021(17) N5 0.018(2) 0.023(2) 0.0049(18) 0.0014(16) -0.0014(15) 0.0051(17) N6 0.021(2) 0.022(2) 0.0108(18) -0.0012(17) -0.0029(17) 0.0036(17) O1 0.0246(18) 0.023(2) 0.0114(19) -0.0017(14) 0.0024(14) -0.0037(14) O2 0.0225(18) 0.023(2) 0.0112(18) -0.0001(14) -0.0006(14) 0.0030(14) O1W 0.022(2) 0.047(3) 0.018(2) 0.0056(17) -0.0010(15) -0.0027(16) S1 0.0226(6) 0.0240(7) 0.0095(6) -0.0026(5) 0.0012(4) -0.0035(5) S2 0.0249(7) 0.0244(7) 0.0083(6) -0.0021(5) 0.0012(4) 0.0052(5) _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 C1 O1 1.328(6) . ? C1 C2 1.410(7) . ? C1 C6 1.414(6) . ? C2 C3 1.385(7) . ? C2 H2A 0.9500 . ? C3 C4 1.390(7) . ? C3 H3A 0.9500 . ? C4 C5 1.370(7) . ? C4 Cl1 1.745(5) . ? C5 C6 1.403(7) . ? C5 H5A 0.9500 . ? C6 C7 1.451(7) . ? C7 N1 1.288(6) . ? C7 H7A 0.9500 . ? C8 N2 1.315(6) . ? C8 N3 1.343(6) . ? C8 S1 1.752(5) . ? C9 N3 1.436(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 O2 1.336(6) . ? C10 C11 1.406(7) . ? C10 C15 1.406(6) . ? C11 C12 1.387(7) . ? C11 H11A 0.9500 . ? C12 C13 1.393(7) . ? C12 H12A 0.9500 . ? C13 C14 1.378(7) . ? C13 Cl2 1.738(5) . ? C14 C15 1.407(7) . ? C14 H14A 0.9500 . ? C15 C16 1.437(7) . ? C16 N4 1.292(6) . ? C16 H16A 0.9500 . ? C17 N6 1.324(6) . ? C17 N5 1.334(6) . ? C17 S2 1.712(5) . ? C18 N6 1.451(6) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? Fe1 O2 1.933(3) . ? Fe1 N1 1.934(4) . ? Fe1 O1 1.940(4) . ? Fe1 N4 1.948(4) . ? Fe1 S1 2.2390(15) . ? Fe1 S2 2.2566(15) . ? N1 N2 1.411(5) . ? N3 H3B 0.8800 . ? N4 N5 1.400(5) . ? N5 H5N 0.8800 . ? N6 H6A 0.8800 . ? O1W H2W 0.8513 . ? O1W H1W 0.8481 . ? 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 O1 C1 C2 118.8(4) . . ? O1 C1 C6 123.8(4) . . ? C2 C1 C6 117.4(4) . . ? C3 C2 C1 122.3(5) . . ? C3 C2 H2A 118.9 . . ? C1 C2 H2A 118.9 . . ? C2 C3 C4 118.8(5) . . ? C2 C3 H3A 120.6 . . ? C4 C3 H3A 120.6 . . ? C5 C4 C3 120.9(5) . . ? C5 C4 Cl1 119.4(4) . . ? C3 C4 Cl1 119.6(4) . . ? C4 C5 C6 120.8(5) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C5 C6 C1 119.8(4) . . ? C5 C6 C7 116.5(4) . . ? C1 C6 C7 123.7(4) . . ? N1 C7 C6 125.6(4) . . ? N1 C7 H7A 117.2 . . ? C6 C7 H7A 117.2 . . ? N2 C8 N3 117.1(4) . . ? N2 C8 S1 124.1(4) . . ? N3 C8 S1 118.7(4) . . ? N3 C9 H9A 109.5 . . ? N3 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N3 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C11 118.4(4) . . ? O2 C10 C15 124.2(4) . . ? C11 C10 C15 117.4(4) . . ? C12 C11 C10 122.0(5) . . ? C12 C11 H11A 119.0 . . ? C10 C11 H11A 119.0 . . ? C11 C12 C13 119.3(5) . . ? C11 C12 H12A 120.4 . . ? C13 C12 H12A 120.4 . . ? C14 C13 C12 120.5(5) . . ? C14 C13 Cl2 119.4(4) . . ? C12 C13 Cl2 120.1(4) . . ? C13 C14 C15 120.1(5) . . ? C13 C14 H14A 119.9 . . ? C15 C14 H14A 119.9 . . ? C10 C15 C14 120.6(4) . . ? C10 C15 C16 123.8(4) . . ? C14 C15 C16 115.6(4) . . ? N4 C16 C15 124.6(4) . . ? N4 C16 H16A 117.7 . . ? C15 C16 H16A 117.7 . . ? N6 C17 N5 117.1(4) . . ? N6 C17 S2 122.3(4) . . ? N5 C17 S2 120.6(3) . . ? N6 C18 H18A 109.5 . . ? N6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O2 Fe1 N1 91.54(16) . . ? O2 Fe1 O1 89.57(15) . . ? N1 Fe1 O1 93.65(16) . . ? O2 Fe1 N4 92.24(16) . . ? N1 Fe1 N4 174.92(19) . . ? O1 Fe1 N4 89.77(16) . . ? O2 Fe1 S1 89.62(12) . . ? N1 Fe1 S1 85.95(13) . . ? O1 Fe1 S1 179.08(13) . . ? N4 Fe1 S1 90.68(13) . . ? O2 Fe1 S2 178.33(13) . . ? N1 Fe1 S2 89.65(13) . . ? O1 Fe1 S2 89.19(12) . . ? N4 Fe1 S2 86.64(13) . . ? S1 Fe1 S2 91.63(5) . . ? C7 N1 N2 112.2(4) . . ? C7 N1 Fe1 126.0(3) . . ? N2 N1 Fe1 121.6(3) . . ? C8 N2 N1 113.0(4) . . ? C8 N3 C9 124.9(4) . . ? C8 N3 H3B 117.6 . . ? C9 N3 H3B 117.6 . . ? C16 N4 N5 115.1(4) . . ? C16 N4 Fe1 127.6(3) . . ? N5 N4 Fe1 117.2(3) . . ? C17 N5 N4 118.9(4) . . ? C17 N5 H5N 120.6 . . ? N4 N5 H5N 120.6 . . ? C17 N6 C18 123.4(4) . . ? C17 N6 H6A 118.3 . . ? C18 N6 H6A 118.3 . . ? C1 O1 Fe1 126.4(3) . . ? C10 O2 Fe1 126.9(3) . . ? H2W O1W H1W 115.8 . . ? C8 S1 Fe1 95.35(17) . . ? C17 S2 Fe1 96.71(17) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.756 _refine_diff_density_min -0.551 _refine_diff_density_rms 0.120 _database_code_depnum_ccdc_archive 'CCDC 936362'