# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'James Gardinier' _publ_contact_author_email james.gardinier@marquette.edu _publ_author_name J.R.Gardinier # Attachment '- FeClpzR4lutCl_06022011.cif' data_1x2MeOH_GARD10Q _database_code_depnum_ccdc_archive 'CCDC 821757' #TrackingRef '- FeClpzR4lutCl_06022011.cif' _audit_creation_date 2011-06-01 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H17 Cl Fe N9, Cl, 2(C H4 O)' _chemical_formula_sum 'C21 H25 Cl2 Fe N9 O2' _chemical_formula_weight 562.25 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C19 H17 N9 Fe Cl2 O' 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' 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' 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' _space_group_crystal_system orthorhombic _space_group_IT_number 36 _space_group_name_H-M_alt 'C m c 21' _space_group_name_Hall 'C 2c -2' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x, y, z' 4 'x, -y, z+1/2' 5 'x+1/2, y+1/2, z' 6 '-x+1/2, -y+1/2, z+1/2' 7 '-x+1/2, y+1/2, z' 8 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.8184(2) _cell_length_b 11.02252(16) _cell_length_c 18.9571(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2469.51(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5134 _cell_measurement_temperature 100 _cell_measurement_theta_max 70.5954 _cell_measurement_theta_min 4.6613 _exptl_absorpt_coefficient_mu 7.216 _exptl_absorpt_correction_T_max 0.837 _exptl_absorpt_correction_T_min 0.465 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.512 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1160 _exptl_crystal_size_max 0.2109 _exptl_crystal_size_mid 0.0441 _exptl_crystal_size_min 0.0262 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_unetI/netI 0.0226 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 7450 _diffrn_reflns_theta_full 70.73 _diffrn_reflns_theta_max 70.73 _diffrn_reflns_theta_min 4.67 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 10.3756 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -64.00 37.00 1.0000 7.4900 omega____ theta____ kappa____ phi______ frames - -40.7737 77.0000 -90.0000 101 #__ type_ start__ end____ width___ exp.time_ 2 omega -105.00 -64.00 1.0000 7.4900 omega____ theta____ kappa____ phi______ frames - -40.7737 -141.0000 -102.0000 41 #__ type_ start__ end____ width___ exp.time_ 3 omega -115.00 -90.00 1.0000 7.4900 omega____ theta____ kappa____ phi______ frames - -40.7737 -141.0000 44.0000 25 #__ type_ start__ end____ width___ exp.time_ 4 omega 73.00 133.00 1.0000 47.1800 omega____ theta____ kappa____ phi______ frames - 100.5756 46.0000 -117.0000 60 #__ type_ start__ end____ width___ exp.time_ 5 omega 110.00 159.00 1.0000 47.1800 omega____ theta____ kappa____ phi______ frames - 100.5756 125.0000 -90.0000 49 #__ type_ start__ end____ width___ exp.time_ 6 omega 26.00 76.00 1.0000 47.1800 omega____ theta____ kappa____ phi______ frames - 100.5756 -45.0000 -90.0000 50 #__ type_ start__ end____ width___ exp.time_ 7 omega 16.00 113.00 1.0000 47.1800 omega____ theta____ kappa____ phi______ frames - 100.5756 0.0000 30.0000 97 #__ type_ start__ end____ width___ exp.time_ 8 omega 7.00 119.00 1.0000 7.4900 omega____ theta____ kappa____ phi______ frames - 40.7737 77.0000 150.0000 112 #__ type_ start__ end____ width___ exp.time_ 9 omega 7.00 119.00 1.0000 7.4900 omega____ theta____ kappa____ phi______ frames - 40.7737 77.0000 0.0000 112 #__ type_ start__ end____ width___ exp.time_ 10 omega 94.00 176.00 1.0000 47.1800 omega____ theta____ kappa____ phi______ frames - 100.5756 125.0000 150.0000 82 #__ type_ start__ end____ width___ exp.time_ 11 omega 26.00 77.00 1.0000 47.1800 omega____ theta____ kappa____ phi______ frames - 100.5756 -45.0000 150.0000 51 #__ type_ start__ end____ width___ exp.time_ 12 omega 26.00 77.00 1.0000 47.1800 omega____ theta____ kappa____ phi______ frames - 100.5756 -45.0000 30.0000 51 #__ type_ start__ end____ width___ exp.time_ 13 omega 73.00 175.00 1.0000 47.1800 omega____ theta____ kappa____ phi______ frames - 100.5756 45.0000 60.0000 102 #__ type_ start__ end____ width___ exp.time_ 14 omega 23.00 56.00 1.0000 7.4900 omega____ theta____ kappa____ phi______ frames - 40.7737 -125.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 15 omega 8.00 118.00 1.0000 7.4900 omega____ theta____ kappa____ phi______ frames - 40.7737 74.0000 -97.0000 110 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0719818000 _diffrn_orient_matrix_UB_12 0.1096026000 _diffrn_orient_matrix_UB_13 -0.0230891000 _diffrn_orient_matrix_UB_21 -0.0161101000 _diffrn_orient_matrix_UB_22 -0.0364176000 _diffrn_orient_matrix_UB_23 -0.0778104000 _diffrn_orient_matrix_UB_31 -0.1074462000 _diffrn_orient_matrix_UB_32 0.0787906000 _diffrn_orient_matrix_UB_33 -0.0038304000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_source 'SuperNova (Cu) X-ray Source' _reflns_number_gt 2220 _reflns_number_total 2296 _reflns_odcompleteness_completeness 99.84 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 64.99 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.143 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.060 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(18) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2296 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0293 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.2240P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0780 _refine_ls_wR_factor_ref 0.0783 _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. The hydrogen atoms were put in geometrically calculated positions with Uiso = 1.2 Uiso/eq of an adjacent atom (1.5 Uiso/eq for methyl groups and hydroxyls) and refined within a riding model using appropriate fixed distances to the adjacent atoms. The methyl and H2 hydroxy hydrogens' positions were optimized rotationally to fit the residual electron density. Hydroxy atom H1 has its y and z coordinates refined with O-H distance constrained. The space group was chosen because the structure is non-centrosymmetric but its cations emulate a second, pseudo mirror plane (apparent space group is Cmcm). This pseudo-symmetry is broken by solvent molecules. The resulting structure either represents a racemic twin (and was handled this way) or the anomalous contributions from solvate oxygens are not enough to break the apparent centrosymmetric statistics. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.5000 0.36450(5) 0.59081(3) 0.01154(14) Uani 1 2 d S . . Cl1 Cl 0.5000 0.15125(6) 0.58797(6) 0.01660(17) Uani 1 2 d S . . N1 N 0.5000 0.5694(2) 0.58899(18) 0.0125(5) Uani 1 2 d S . . N11 N 0.6374(2) 0.3926(2) 0.51628(12) 0.0152(5) Uani 1 1 d . . . N12 N 0.7151(2) 0.4814(2) 0.52784(14) 0.0159(5) Uani 1 1 d . . . N21 N 0.6342(2) 0.3974(2) 0.66707(12) 0.0167(5) Uani 1 1 d . . . N22 N 0.7133(2) 0.4843(2) 0.65412(14) 0.0145(5) Uani 1 1 d . . . C1 C 0.70537(19) 0.5571(2) 0.59013(19) 0.0165(5) Uani 1 1 d . . . H1 H 0.7705 0.6150 0.5900 0.020 Uiso 1 1 calc R . . C2 C 0.59677(19) 0.6316(2) 0.58988(18) 0.0141(4) Uani 1 1 d . . . C3 C 0.6007(2) 0.7574(2) 0.59297(18) 0.0196(5) Uani 1 1 d . . . H3 H 0.6712 0.7988 0.5942 0.024 Uiso 1 1 calc R . . C4 C 0.5000 0.8211(3) 0.5943(3) 0.0235(8) Uani 1 2 d S . . H4 H 0.5000 0.9072 0.5961 0.028 Uiso 1 2 calc SR . . C11 C 0.6690(3) 0.3404(3) 0.45554(15) 0.0179(6) Uani 1 1 d . . . H11 H 0.6313 0.2737 0.4342 0.021 Uiso 1 1 calc R . . C12 C 0.7647(3) 0.3972(3) 0.42782(17) 0.0246(7) Uani 1 1 d . . . H12 H 0.8026 0.3783 0.3850 0.030 Uiso 1 1 calc R . . C13 C 0.7922(3) 0.4857(3) 0.47522(18) 0.0220(7) Uani 1 1 d . . . H13 H 0.8542 0.5403 0.4719 0.026 Uiso 1 1 calc R . . C21 C 0.6590(3) 0.3543(3) 0.73059(16) 0.0197(6) Uani 1 1 d . . . H21 H 0.6185 0.2916 0.7539 0.024 Uiso 1 1 calc R . . C22 C 0.7541(3) 0.4147(3) 0.75846(15) 0.0236(6) Uani 1 1 d . . . H22 H 0.7884 0.4012 0.8031 0.028 Uiso 1 1 calc R . . C23 C 0.7867(3) 0.4961(3) 0.70858(16) 0.0211(7) Uani 1 1 d . . . H23 H 0.8488 0.5506 0.7114 0.025 Uiso 1 1 calc R . . Cl2 Cl 0.5000 0.89768(8) 0.31151(4) 0.01582(18) Uani 1 2 d S . . O1 O 0.5000 0.1687(3) 0.35988(17) 0.0305(7) Uani 1 2 d SD . . H1A H 0.5000 0.098(3) 0.345(3) 0.046 Uiso 1 2 d SD . . C1S C 0.5000 0.2510(4) 0.3020(2) 0.0337(11) Uani 1 2 d S . . H1SA H 0.4701 0.2102 0.2600 0.051 Uiso 0.50 1 calc PR A -1 H1SB H 0.5775 0.2783 0.2928 0.051 Uiso 0.50 1 calc PR A -1 H1SC H 0.4524 0.3211 0.3134 0.051 Uiso 0.50 1 calc PR A -1 O2 O 0.5517(5) 0.6916(5) 0.4270(3) 0.0541(16) Uani 0.50 1 d P B -1 H2 H 0.5477 0.7538 0.4016 0.081 Uiso 0.50 1 calc PR B -1 C2S C 0.4793(9) 0.6010(5) 0.3997(3) 0.031(3) Uani 0.50 1 d P B -1 H2SA H 0.4891 0.5958 0.3484 0.047 Uiso 0.50 1 calc PR B -1 H2SB H 0.4006 0.6218 0.4105 0.047 Uiso 0.50 1 calc PR B -1 H2SC H 0.4981 0.5227 0.4211 0.047 Uiso 0.50 1 calc PR B -1 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 0.0102(2) 0.0080(2) 0.0164(2) -0.0005(2) 0.000 0.000 Cl1 0.0143(3) 0.0097(3) 0.0258(4) 0.0001(4) 0.000 0.000 N1 0.0136(13) 0.0110(12) 0.0129(11) -0.0004(14) 0.000 0.000 N11 0.0119(11) 0.0136(10) 0.0201(10) 0.0003(10) 0.0011(9) 0.0000(11) N12 0.0139(13) 0.0114(11) 0.0225(13) 0.0011(9) 0.0007(10) 0.0000(9) N21 0.0126(11) 0.0145(11) 0.0228(11) -0.0004(10) -0.0011(10) -0.0009(11) N22 0.0101(13) 0.0130(11) 0.0205(12) -0.0012(9) -0.0009(10) -0.0009(9) C1 0.0125(11) 0.0125(10) 0.0244(11) -0.0012(14) -0.0002(12) -0.0032(9) C2 0.0146(11) 0.0113(10) 0.0164(10) 0.0024(11) -0.0013(15) 0.0005(9) C3 0.0197(12) 0.0138(12) 0.0254(12) -0.0031(13) -0.0012(16) -0.0046(9) C4 0.0265(19) 0.0107(15) 0.0333(19) 0.002(2) 0.000 0.000 C11 0.0188(16) 0.0164(13) 0.0184(14) -0.0022(11) -0.0001(12) -0.0013(12) C12 0.0251(18) 0.0281(15) 0.0206(13) -0.0009(12) 0.0087(12) 0.0024(15) C13 0.0156(17) 0.0224(15) 0.0280(17) 0.0051(12) 0.0064(13) -0.0039(12) C21 0.0189(15) 0.0209(15) 0.0194(14) 0.0037(11) 0.0003(12) 0.0017(12) C22 0.0227(16) 0.0296(16) 0.0185(12) -0.0005(12) -0.0062(11) -0.0011(14) C23 0.0162(18) 0.0221(16) 0.0251(18) -0.0040(11) -0.0046(11) 0.0000(12) Cl2 0.0130(4) 0.0181(4) 0.0164(3) 0.0007(4) 0.000 0.000 O1 0.0332(18) 0.0255(15) 0.0327(17) -0.0146(14) 0.000 0.000 C1S 0.033(3) 0.036(3) 0.032(2) -0.0108(19) 0.000 0.000 O2 0.075(4) 0.038(3) 0.049(3) 0.018(2) -0.036(3) -0.026(3) C2S 0.033(10) 0.028(3) 0.033(3) 0.005(2) -0.003(3) -0.005(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 Cl1 2.3512(9) . ? Fe1 N1 2.258(3) . ? Fe1 N11 2.175(2) 3_655 ? Fe1 N11 2.175(2) . ? Fe1 N21 2.177(2) 3_655 ? Fe1 N21 2.177(2) . ? N1 C2 1.334(3) 3_655 ? N1 C2 1.334(3) . ? N11 N12 1.360(3) . ? N11 C11 1.340(4) . ? N12 C1 1.450(4) . ? N12 C13 1.353(4) . ? N21 N22 1.361(3) . ? N21 C21 1.327(4) . ? N22 C1 1.457(4) . ? N22 C23 1.355(4) . ? C1 H1 1.0000 . ? C1 C2 1.524(3) . ? C2 C3 1.389(3) . ? C3 H3 0.9500 . ? C3 C4 1.382(3) . ? C4 C3 1.382(3) 3_655 ? C4 H4 0.9500 . ? C11 H11 0.9500 . ? C11 C12 1.395(5) . ? C12 H12 0.9500 . ? C12 C13 1.366(5) . ? C13 H13 0.9500 . ? C21 H21 0.9500 . ? C21 C22 1.408(5) . ? C22 H22 0.9500 . ? C22 C23 1.360(5) . ? C23 H23 0.9500 . ? O1 H1A 0.83(2) . ? O1 C1S 1.423(6) . ? C1S H1SA 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SC 0.9800 . ? O2 H2 0.8400 . ? O2 C2S 1.412(9) . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 0.9800 . ? 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 N1 Fe1 Cl1 177.81(10) . . ? N11 Fe1 Cl1 97.33(7) 3_655 . ? N11 Fe1 Cl1 97.33(7) . . ? N11 Fe1 N1 81.24(9) 3_655 . ? N11 Fe1 N1 81.24(9) . . ? N11 Fe1 N11 96.63(13) 3_655 . ? N11 Fe1 N21 82.15(7) 3_655 3_655 ? N11 Fe1 N21 162.18(7) . 3_655 ? N11 Fe1 N21 162.18(7) 3_655 . ? N11 Fe1 N21 82.15(7) . . ? N21 Fe1 Cl1 100.46(7) 3_655 . ? N21 Fe1 Cl1 100.46(7) . . ? N21 Fe1 N1 81.01(9) . . ? N21 Fe1 N1 81.01(9) 3_655 . ? N21 Fe1 N21 93.58(13) 3_655 . ? C2 N1 Fe1 120.94(14) 3_655 . ? C2 N1 Fe1 120.94(14) . . ? C2 N1 C2 118.1(3) . 3_655 ? N12 N11 Fe1 120.12(18) . . ? C11 N11 Fe1 134.8(2) . . ? C11 N11 N12 105.0(2) . . ? N11 N12 C1 119.5(2) . . ? C13 N12 N11 111.2(3) . . ? C13 N12 C1 129.3(3) . . ? N22 N21 Fe1 119.86(18) . . ? C21 N21 Fe1 134.7(2) . . ? C21 N21 N22 105.3(3) . . ? N21 N22 C1 119.6(2) . . ? C23 N22 N21 111.7(2) . . ? C23 N22 C1 128.5(2) . . ? N12 C1 N22 110.89(18) . . ? N12 C1 H1 107.7 . . ? N12 C1 C2 112.0(3) . . ? N22 C1 H1 107.7 . . ? N22 C1 C2 110.7(2) . . ? C2 C1 H1 107.7 . . ? N1 C2 C1 116.4(2) . . ? N1 C2 C3 122.9(2) . . ? C3 C2 C1 120.7(2) . . ? C2 C3 H3 120.7 . . ? C4 C3 C2 118.6(2) . . ? C4 C3 H3 120.7 . . ? C3 C4 C3 118.9(3) 3_655 . ? C3 C4 H4 120.6 . . ? C3 C4 H4 120.6 3_655 . ? N11 C11 H11 124.5 . . ? N11 C11 C12 110.9(3) . . ? C12 C11 H11 124.5 . . ? C11 C12 H12 127.3 . . ? C13 C12 C11 105.4(3) . . ? C13 C12 H12 127.3 . . ? N12 C13 C12 107.4(3) . . ? N12 C13 H13 126.3 . . ? C12 C13 H13 126.3 . . ? N21 C21 H21 124.8 . . ? N21 C21 C22 110.3(3) . . ? C22 C21 H21 124.8 . . ? C21 C22 H22 127.0 . . ? C23 C22 C21 106.1(3) . . ? C23 C22 H22 127.0 . . ? N22 C23 C22 106.6(3) . . ? N22 C23 H23 126.7 . . ? C22 C23 H23 126.7 . . ? C1S O1 H1A 109(4) . . ? O1 C1S H1SA 109.5 . . ? O1 C1S H1SB 109.5 . . ? O1 C1S H1SC 109.5 . . ? C2S O2 H2 109.5 . . ? 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 O1 H1A Cl2 0.83(2) 2.30(2) 3.125(4) 175(6) 1_545 O2 H2 Cl2 0.84 2.40 3.214(5) 164.2 . 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 Fe1 N1 C2 C1 1.6(4) . . . . ? Fe1 N1 C2 C3 -176.1(3) . . . . ? Fe1 N11 N12 C1 0.0(3) . . . . ? Fe1 N11 N12 C13 -179.0(2) . . . . ? Fe1 N11 C11 C12 178.5(2) . . . . ? Fe1 N21 N22 C1 1.7(3) . . . . ? Fe1 N21 N22 C23 177.0(2) . . . . ? Fe1 N21 C21 C22 -176.1(2) . . . . ? Cl1 Fe1 N1 C2 -91.4(3) . . . . ? Cl1 Fe1 N1 C2 91.4(3) . . . 3_655 ? Cl1 Fe1 N11 N12 -140.26(19) . . . . ? Cl1 Fe1 N11 C11 40.0(3) . . . . ? Cl1 Fe1 N21 N22 135.63(19) . . . . ? Cl1 Fe1 N21 C21 -48.3(3) . . . . ? N1 Fe1 N11 N12 41.4(2) . . . . ? N1 Fe1 N11 C11 -138.3(3) . . . . ? N1 Fe1 N21 N22 -42.7(2) . . . . ? N1 Fe1 N21 C21 133.4(3) . . . . ? N1 C2 C3 C4 -0.8(6) . . . . ? N11 Fe1 N1 C2 140.5(3) . . . 3_655 ? N11 Fe1 N1 C2 -140.5(3) 3_655 . . . ? N11 Fe1 N1 C2 42.3(3) 3_655 . . 3_655 ? N11 Fe1 N1 C2 -42.3(3) . . . . ? N11 Fe1 N11 N12 121.44(17) 3_655 . . . ? N11 Fe1 N11 C11 -58.3(3) 3_655 . . . ? N11 Fe1 N21 N22 -47.7(5) 3_655 . . . ? N11 Fe1 N21 N22 39.58(18) . . . . ? N11 Fe1 N21 C21 128.4(4) 3_655 . . . ? N11 Fe1 N21 C21 -144.3(3) . . . . ? N11 N12 C1 N22 61.0(3) . . . . ? N11 N12 C1 C2 -63.2(3) . . . . ? N11 N12 C13 C12 -0.1(4) . . . . ? N11 C11 C12 C13 1.2(4) . . . . ? N12 N11 C11 C12 -1.2(3) . . . . ? N12 C1 C2 N1 60.8(4) . . . . ? N12 C1 C2 C3 -121.3(3) . . . . ? N21 Fe1 N1 C2 41.1(3) . . . . ? N21 Fe1 N1 C2 -136.2(3) . . . 3_655 ? N21 Fe1 N1 C2 -41.1(3) 3_655 . . 3_655 ? N21 Fe1 N1 C2 136.2(3) 3_655 . . . ? N21 Fe1 N11 N12 -40.64(19) . . . . ? N21 Fe1 N11 N12 36.5(5) 3_655 . . . ? N21 Fe1 N11 C11 -143.2(3) 3_655 . . . ? N21 Fe1 N11 C11 139.7(3) . . . . ? N21 Fe1 N21 N22 -123.03(17) 3_655 . . . ? N21 Fe1 N21 C21 53.1(3) 3_655 . . . ? N21 N22 C1 N12 -62.1(3) . . . . ? N21 N22 C1 C2 62.8(3) . . . . ? N21 N22 C23 C22 -0.2(4) . . . . ? N21 C21 C22 C23 -0.5(4) . . . . ? N22 N21 C21 C22 0.4(3) . . . . ? N22 C1 C2 N1 -63.5(4) . . . . ? N22 C1 C2 C3 114.4(3) . . . . ? C1 N12 C13 C12 -178.9(3) . . . . ? C1 N22 C23 C22 174.5(3) . . . . ? C1 C2 C3 C4 -178.5(4) . . . . ? C2 N1 C2 C1 178.9(2) 3_655 . . . ? C2 N1 C2 C3 1.2(6) 3_655 . . . ? C2 C3 C4 C3 0.4(7) . . . 3_655 ? C11 N11 N12 C1 179.8(3) . . . . ? C11 N11 N12 C13 0.8(3) . . . . ? C11 C12 C13 N12 -0.7(4) . . . . ? C13 N12 C1 N22 -120.2(3) . . . . ? C13 N12 C1 C2 115.6(3) . . . . ? C21 N21 N22 C1 -175.4(3) . . . . ? C21 N21 N22 C23 -0.1(3) . . . . ? C21 C22 C23 N22 0.4(4) . . . . ? C23 N22 C1 N12 123.4(3) . . . . ? C23 N22 C1 C2 -111.7(3) . . . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 0 -12 0.1034 -0.0114 -0.0045 -11.9876 0.2771 0.9337 0.0460 0 0 12 0.1034 0.0114 0.0045 11.9876 -0.2771 -0.9337 -0.0460 3 7 1 0.0183 2.9886 7.0032 0.9878 0.9601 -0.3811 0.2254 -3 -7 -1 0.0183 -2.9886 -7.0032 -0.9878 -0.9601 0.3811 -0.2254 6 -4 0 0.0131 6.0003 -3.9897 -0.0111 -0.0065 0.0490 -0.9598 -6 4 0 0.0131 -6.0003 3.9897 0.0111 0.0065 -0.0490 0.9598 #==END data_1xMeOH_GARD10PC _database_code_depnum_ccdc_archive 'CCDC 821758' #TrackingRef '- FeClpzR4lutCl_06022011.cif' _audit_creation_date 2011-05-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety '2(C9.5 H8.5 Cl0.5 Fe0.5 N4.5), Cl, C H4 O' _chemical_formula_sum 'C20 H21 Cl2 Fe N9 O' _chemical_formula_weight 530.21 _chemical_melting_point ? 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' 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' 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' _space_group_crystal_system orthorhombic _space_group_IT_number 64 _space_group_name_H-M_alt 'C m c a' _space_group_name_Hall '-C 2bc 2' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y+1/2, z+1/2' 3 'x, -y, -z' 4 '-x, y+1/2, -z+1/2' 5 'x+1/2, y+1/2, z' 6 '-x+1/2, -y+1, z+1/2' 7 'x+1/2, -y+1/2, -z' 8 '-x+1/2, y+1, -z+1/2' 9 '-x, -y, -z' 10 'x, y-1/2, -z-1/2' 11 '-x, y, z' 12 'x, -y-1/2, z-1/2' 13 '-x+1/2, -y+1/2, -z' 14 'x+1/2, y, -z-1/2' 15 '-x+1/2, y+1/2, z' 16 'x+1/2, -y, z-1/2' _cell_length_a 21.641(4) _cell_length_b 22.294(4) _cell_length_c 9.5986(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4631.0(15) _cell_formula_units_Z 8 _cell_measurement_reflns_used 13123 _cell_measurement_temperature 100 _cell_measurement_theta_max 29.3886 _cell_measurement_theta_min 3.3189 _exptl_absorpt_coefficient_mu 0.915 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.85412 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2176 _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_special_details ? _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_unetI/netI 0.0131 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 16592 _diffrn_reflns_theta_full 29.00 _diffrn_reflns_theta_max 29.45 _diffrn_reflns_theta_min 3.37 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 10.3756 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.920 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 24.00 52.00 1.0000 19.0100 omega____ theta____ kappa____ phi______ frames - 11.5134 -96.0000 78.0000 28 #__ type_ start__ end____ width___ exp.time_ 2 omega -67.00 47.00 1.0000 19.0100 omega____ theta____ kappa____ phi______ frames - 11.5134 0.0000 120.0000 114 #__ type_ start__ end____ width___ exp.time_ 3 omega -90.00 -43.00 1.0000 19.0100 omega____ theta____ kappa____ phi______ frames - -11.6697 -77.0000 -180.0000 47 #__ type_ start__ end____ width___ exp.time_ 4 omega -28.00 64.00 1.0000 19.0100 omega____ theta____ kappa____ phi______ frames - -11.6697 37.0000 -60.0000 92 ; _diffrn_measurement_device_type 'SuperNova, Dual, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0388231 _diffrn_orient_matrix_UB_12 -0.0179246 _diffrn_orient_matrix_UB_13 0.0208949 _diffrn_orient_matrix_UB_21 0.0040469 _diffrn_orient_matrix_UB_22 0.0230798 _diffrn_orient_matrix_UB_23 0.0224912 _diffrn_orient_matrix_UB_31 -0.0627366 _diffrn_orient_matrix_UB_32 0.0125824 _diffrn_orient_matrix_UB_33 -0.011486 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_source 'fine-focus sealed tube' _reflns_number_gt 2641 _reflns_number_total 3038 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.386 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 167 _refine_ls_number_reflns 3038 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0234 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+3.5110P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0663 _refine_ls_wR_factor_ref 0.0678 _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. The hydrogen atoms were put in geometrically calculated positions with Uiso = 1.2 Uiso/eq of an adjacent atom (1.5 Uiso/eq for methyl groups and hydroxyls) and refined within a riding model using appropriate fixed distances to the adjacent atoms. The methyl and hydroxy hydrogens' positions were optimized rotationally to fit the residual electron density ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.5000 0.350008(10) 0.76084(2) 0.01188(8) Uani 1 2 d S . . Cl1 Cl 0.5000 0.246267(17) 0.75403(4) 0.01745(10) Uani 1 2 d S . . N1 N 0.5000 0.45019(6) 0.78255(15) 0.0149(3) Uani 1 2 d S . . N11 N 0.42278(5) 0.35876(4) 0.90931(11) 0.0160(2) Uani 1 1 d . . . N12 N 0.38021(5) 0.40286(4) 0.88994(11) 0.0169(2) Uani 1 1 d . . . N21 N 0.42706(5) 0.37121(4) 0.61091(10) 0.0159(2) Uani 1 1 d . . . N22 N 0.38444(5) 0.41384(4) 0.64418(11) 0.0163(2) Uani 1 1 d . . . C1 C 0.38755(6) 0.44530(5) 0.77642(13) 0.0167(2) Uani 1 1 d . . . H1 H 0.3522 0.4741 0.7803 0.020 Uiso 1 1 calc R . . C2 C 0.44686(6) 0.48098(5) 0.78890(13) 0.0161(2) Uani 1 1 d . . . C3 C 0.44487(6) 0.54296(5) 0.80180(14) 0.0202(3) Uani 1 1 d . . . H3 H 0.4064 0.5634 0.8062 0.024 Uiso 1 1 calc R . . C4 C 0.5000 0.57439(7) 0.8082(2) 0.0226(4) Uani 1 2 d S . . H4 H 0.5000 0.6168 0.8169 0.027 Uiso 1 2 calc SR . . C11 C 0.39883(6) 0.32385(5) 1.00863(13) 0.0191(2) Uani 1 1 d . . . H11 H 0.4184 0.2891 1.0450 0.023 Uiso 1 1 calc R . . C12 C 0.34103(6) 0.34525(6) 1.05223(14) 0.0235(3) Uani 1 1 d . . . H12 H 0.3148 0.3284 1.1213 0.028 Uiso 1 1 calc R . . C13 C 0.33040(6) 0.39567(6) 0.97394(14) 0.0223(3) Uani 1 1 d . . . H13 H 0.2949 0.4207 0.9778 0.027 Uiso 1 1 calc R . . C21 C 0.40867(6) 0.34983(5) 0.48804(13) 0.0180(2) Uani 1 1 d . . . H21 H 0.4294 0.3192 0.4378 0.022 Uiso 1 1 calc R . . C22 C 0.35460(6) 0.37855(6) 0.44271(13) 0.0214(3) Uani 1 1 d . . . H22 H 0.3325 0.3713 0.3589 0.026 Uiso 1 1 calc R . . C23 C 0.34047(6) 0.41913(5) 0.54479(13) 0.0189(2) Uani 1 1 d . . . H23 H 0.3063 0.4459 0.5457 0.023 Uiso 1 1 calc R . . Cl2 Cl 0.2500 0.521452(18) 0.7500 0.01766(10) Uani 1 2 d S . . O1 O 0.23059(12) 0.24328(10) 0.6786(3) 0.0416(6) Uani 0.50 1 d PD A -1 H1a H 0.1998 0.2572 0.6362 0.062 Uiso 0.50 1 calc PR A -1 C1s C 0.2549(12) 0.28724(17) 0.7666(17) 0.076(3) Uani 0.50 1 d PD A -1 H1sa H 0.2937 0.3024 0.7275 0.114 Uiso 0.50 1 calc PR A -1 H1sb H 0.2627 0.2699 0.8587 0.114 Uiso 0.50 1 calc PR A -1 H1sc H 0.2253 0.3203 0.7752 0.114 Uiso 0.50 1 calc PR A -1 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 0.00912(13) 0.00986(11) 0.01667(13) -0.00123(8) 0.000 0.000 Cl1 0.0195(2) 0.01121(17) 0.0217(2) 0.00081(14) 0.000 0.000 N1 0.0125(7) 0.0121(6) 0.0202(7) -0.0025(5) 0.000 0.000 N11 0.0126(5) 0.0156(4) 0.0198(5) -0.0028(4) -0.0002(4) 0.0015(4) N12 0.0105(5) 0.0181(5) 0.0220(5) -0.0038(4) 0.0013(4) 0.0021(4) N21 0.0135(5) 0.0140(4) 0.0202(5) -0.0014(4) -0.0001(4) 0.0027(4) N22 0.0120(5) 0.0149(4) 0.0220(5) -0.0014(4) -0.0020(4) 0.0031(4) C1 0.0122(6) 0.0151(5) 0.0227(6) -0.0033(4) -0.0007(5) 0.0034(4) C2 0.0144(6) 0.0144(5) 0.0197(6) -0.0013(4) -0.0008(5) 0.0016(4) C3 0.0214(6) 0.0148(5) 0.0242(6) -0.0033(5) -0.0006(5) 0.0050(5) C4 0.0300(10) 0.0115(7) 0.0262(9) -0.0039(7) 0.000 0.000 C11 0.0187(6) 0.0190(6) 0.0196(6) -0.0033(5) 0.0003(5) -0.0033(5) C12 0.0182(6) 0.0279(6) 0.0246(6) -0.0048(5) 0.0060(5) -0.0067(5) C13 0.0112(6) 0.0275(6) 0.0283(7) -0.0089(5) 0.0035(5) -0.0014(5) C21 0.0177(6) 0.0171(5) 0.0193(6) -0.0010(4) -0.0005(5) -0.0009(4) C22 0.0184(6) 0.0241(6) 0.0216(6) 0.0002(5) -0.0047(5) -0.0013(5) C23 0.0124(6) 0.0192(5) 0.0251(6) 0.0033(5) -0.0042(5) 0.0005(4) Cl2 0.01105(19) 0.01716(18) 0.0248(2) 0.000 0.00174(15) 0.000 O1 0.0450(14) 0.0360(12) 0.0438(14) -0.0109(11) -0.0133(12) 0.0077(11) C1s 0.146(8) 0.0321(15) 0.049(7) -0.002(3) -0.040(5) -0.020(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 Fe1 Cl1 2.3137(6) . ? Fe1 N1 2.2432(14) . ? Fe1 N11 2.2049(11) 11_655 ? Fe1 N11 2.2050(11) . ? Fe1 N21 2.1878(10) 11_655 ? Fe1 N21 2.1878(10) . ? N1 C2 1.3407(14) 11_655 ? N1 C2 1.3407(14) . ? N11 C11 1.3353(16) . ? N12 N11 1.3600(14) . ? N12 C1 1.4518(16) . ? N12 C13 1.3557(16) . ? N21 C21 1.3329(16) . ? N22 N21 1.3622(13) . ? N22 C1 1.4517(16) . ? N22 C23 1.3526(16) . ? C1 H1 1.0000 . ? C2 C1 1.5148(17) . ? C2 C3 1.3878(16) . ? C3 H3 0.9500 . ? C3 C4 1.3851(16) . ? C4 C3 1.3851(16) 11_655 ? C4 H4 0.9500 . ? C11 H11 0.9500 . ? C12 C11 1.4027(18) . ? C12 H12 0.9500 . ? C13 C12 1.3714(19) . ? C13 H13 0.9500 . ? C21 H21 0.9500 . ? C22 C21 1.4029(17) . ? C22 H22 0.9500 . ? C23 C22 1.3683(18) . ? C23 H23 0.9500 . ? O1 H1a 0.8400 . ? O1 C1s 1.396(9) . ? C1s H1sa 0.9800 . ? C1s H1sb 0.9800 . ? C1s H1sc 0.9800 . ? 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 N1 Fe1 Cl1 176.29(4) . . ? N11 Fe1 Cl1 96.12(3) 11_655 . ? N11 Fe1 Cl1 96.12(3) . . ? N11 Fe1 N1 81.48(4) . . ? N11 Fe1 N1 81.48(4) 11_655 . ? N11 Fe1 N11 98.56(6) 11_655 . ? N21 Fe1 Cl1 101.39(3) 11_655 . ? N21 Fe1 Cl1 101.39(3) . . ? N21 Fe1 N1 81.14(4) . . ? N21 Fe1 N1 81.14(4) 11_655 . ? N21 Fe1 N11 162.34(4) . 11_655 ? N21 Fe1 N11 81.90(4) 11_655 11_655 ? N21 Fe1 N11 162.34(4) 11_655 . ? N21 Fe1 N11 81.90(4) . . ? N21 Fe1 N21 92.37(6) . 11_655 ? C2 N1 Fe1 120.93(7) 11_655 . ? C2 N1 Fe1 120.93(7) . . ? C2 N1 C2 118.13(14) 11_655 . ? N12 N11 Fe1 119.27(8) . . ? C11 N11 Fe1 134.75(8) . . ? C11 N11 N12 104.83(10) . . ? N11 N12 C1 119.98(10) . . ? C13 N12 N11 111.83(10) . . ? C13 N12 C1 127.61(11) . . ? N22 N21 Fe1 119.02(7) . . ? C21 N21 Fe1 136.07(8) . . ? C21 N21 N22 104.76(10) . . ? N21 N22 C1 120.71(9) . . ? C23 N22 N21 111.82(10) . . ? C23 N22 C1 127.39(10) . . ? N12 C1 H1 107.9 . . ? N12 C1 C2 112.06(10) . . ? N22 C1 N12 109.66(9) . . ? N22 C1 H1 107.9 . . ? N22 C1 C2 111.23(10) . . ? C2 C1 H1 107.9 . . ? N1 C2 C1 117.02(10) . . ? N1 C2 C3 122.71(12) . . ? C3 C2 C1 120.24(11) . . ? C2 C3 H3 120.6 . . ? C4 C3 C2 118.74(12) . . ? C4 C3 H3 120.6 . . ? C3 C4 C3 118.95(15) 11_655 . ? C3 C4 H4 120.5 . . ? C3 C4 H4 120.5 11_655 . ? N11 C11 H11 124.4 . . ? N11 C11 C12 111.15(11) . . ? C12 C11 H11 124.4 . . ? C11 C12 H12 127.3 . . ? C13 C12 C11 105.36(11) . . ? C13 C12 H12 127.3 . . ? N12 C13 C12 106.82(11) . . ? N12 C13 H13 126.6 . . ? C12 C13 H13 126.6 . . ? N21 C21 H21 124.4 . . ? N21 C21 C22 111.12(11) . . ? C22 C21 H21 124.4 . . ? C21 C22 H22 127.3 . . ? C23 C22 C21 105.42(11) . . ? C23 C22 H22 127.3 . . ? N22 C23 C22 106.87(11) . . ? N22 C23 H23 126.6 . . ? C22 C23 H23 126.6 . . ? 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 Fe1 N1 C2 C1 -1.78(17) . . . . ? Fe1 N1 C2 C3 -179.76(10) . . . . ? Fe1 N11 C11 C12 -166.78(9) . . . . ? Fe1 N21 C21 C22 175.22(9) . . . . ? Cl1 Fe1 N1 C2 -90.15(12) . . . . ? Cl1 Fe1 N1 C2 90.15(12) . . . 11_655 ? Cl1 Fe1 N11 N12 -140.22(8) . . . . ? Cl1 Fe1 N11 C11 25.46(12) . . . . ? Cl1 Fe1 N21 N22 135.20(8) . . . . ? Cl1 Fe1 N21 C21 -39.52(12) . . . . ? N1 Fe1 N11 N12 42.64(8) . . . . ? N1 Fe1 N11 C11 -151.68(12) . . . . ? N1 Fe1 N21 N22 -42.04(8) . . . . ? N1 Fe1 N21 C21 143.25(12) . . . . ? N1 C2 C1 N12 62.88(15) . . . . ? N1 C2 C1 N22 -60.27(15) . . . . ? N1 C2 C3 C4 0.1(2) . . . . ? N11 Fe1 N1 C2 -40.13(11) . . . . ? N11 Fe1 N1 C2 140.18(12) . . . 11_655 ? N11 Fe1 N1 C2 40.13(11) 11_655 . . 11_655 ? N11 Fe1 N1 C2 -140.18(12) 11_655 . . . ? N11 Fe1 N11 N12 122.62(7) 11_655 . . . ? N11 Fe1 N11 C11 -71.70(12) 11_655 . . . ? N11 Fe1 N21 N22 40.53(8) . . . . ? N11 Fe1 N21 N22 -52.26(16) 11_655 . . . ? N11 Fe1 N21 C21 -134.18(12) . . . . ? N11 Fe1 N21 C21 133.03(13) 11_655 . . . ? N11 N12 C1 N22 63.31(14) . . . . ? N11 N12 C1 C2 -60.71(13) . . . . ? N11 N12 C13 C12 0.58(14) . . . . ? N12 N11 C11 C12 0.33(13) . . . . ? N12 C13 C12 C11 -0.35(14) . . . . ? N21 Fe1 N1 C2 -136.76(12) . . . 11_655 ? N21 Fe1 N1 C2 -42.94(11) 11_655 . . 11_655 ? N21 Fe1 N1 C2 136.75(12) 11_655 . . . ? N21 Fe1 N1 C2 42.94(11) . . . . ? N21 Fe1 N11 N12 32.43(17) 11_655 . . . ? N21 Fe1 N11 N12 -39.54(8) . . . . ? N21 Fe1 N11 C11 -161.89(12) 11_655 . . . ? N21 Fe1 N11 C11 126.14(12) . . . . ? N21 Fe1 N21 N22 -122.69(7) 11_655 . . . ? N21 Fe1 N21 C21 62.60(13) 11_655 . . . ? N21 N22 C1 N12 -62.29(14) . . . . ? N21 N22 C1 C2 62.22(14) . . . . ? N21 N22 C23 C22 0.07(14) . . . . ? N22 N21 C21 C22 0.00(13) . . . . ? N22 C23 C22 C21 -0.06(14) . . . . ? C1 N12 N11 Fe1 -2.96(13) . . . . ? C1 N12 N11 C11 -172.49(10) . . . . ? C1 N12 C13 C12 171.75(11) . . . . ? C1 N22 N21 Fe1 0.62(14) . . . . ? C1 N22 N21 C21 176.83(10) . . . . ? C1 N22 C23 C22 -176.55(11) . . . . ? C1 C2 C3 C4 -177.83(14) . . . . ? C2 N1 C2 C1 177.92(9) 11_655 . . . ? C2 N1 C2 C3 -0.1(2) 11_655 . . . ? C2 C3 C4 C3 -0.1(3) . . . 11_655 ? C3 C2 C1 N12 -119.09(12) . . . . ? C3 C2 C1 N22 117.76(12) . . . . ? C13 N12 N11 Fe1 168.97(8) . . . . ? C13 N12 N11 C11 -0.57(13) . . . . ? C13 N12 C1 N22 -107.21(13) . . . . ? C13 N12 C1 C2 128.76(13) . . . . ? C13 C12 C11 N11 0.01(15) . . . . ? C23 N22 N21 Fe1 -176.25(8) . . . . ? C23 N22 N21 C21 -0.04(13) . . . . ? C23 N22 C1 N12 114.05(13) . . . . ? C23 N22 C1 C2 -121.43(13) . . . . ? C23 C22 C21 N21 0.04(15) . . . . ? #===END data_2xMeOHxEt2O_gard8ta _database_code_depnum_ccdc_archive 'CCDC 821759' #TrackingRef '- FeClpzR4lutCl_06022011.cif' _audit_creation_date 2011-05-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H25 Cl Fe N9, Cl, C H4 O, 0.348(C4 H10 O)' _chemical_formula_sum 'C25.39 H32.48 Cl2 Fe N9 O1.35' _chemical_formula_weight 612.10 _chemical_melting_point ? 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9870(2) _cell_length_b 16.2105(2) _cell_length_c 14.3844(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.2600(10) _cell_angle_gamma 90.00 _cell_volume 2907.16(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7705 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 67 _cell_measurement_theta_min 4 _exptl_absorpt_coefficient_mu 6.157 _exptl_absorpt_correction_T_max 0.6072 _exptl_absorpt_correction_T_min 0.3875 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1274 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_unetI/netI 0.0243 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 24110 _diffrn_reflns_theta_full 67.69 _diffrn_reflns_theta_max 67.69 _diffrn_reflns_theta_min 4.06 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4562 _reflns_number_total 5191 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_collection 'APEX2 v2.1-4 (Bruker, 2007)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _refine_diff_density_max 0.400 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 364 _refine_ls_number_reflns 5191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0349 _refine_ls_restrained_S_all 1.006 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0540P)^2^+1.3256P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0869 _refine_ls_wR_factor_ref 0.0891 _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. The hydrogen atoms were put in geometrically calculated positions with Uiso = 1.2 Uiso/eq of an adjacent atom (1.5 Uiso/eq for methyl groups and hydroxyls) and refined within a riding model using appropriate fixed distances to the adjacent atoms. The methyl and hydroxy hydrogens' positions were optimized rotationally to fit the residual electron density ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.78407(2) 0.65554(2) 0.12692(2) 0.01765(10) Uani 1 1 d . . . Cl1 Cl 0.89448(4) 0.74634(3) 0.23515(4) 0.02630(13) Uani 1 1 d . . . N9 N 0.68003(14) 0.56741(11) 0.01774(13) 0.0208(4) Uani 1 1 d . . . N11 N 0.90534(14) 0.56586(11) 0.11915(13) 0.0220(4) Uani 1 1 d . . . N12 N 0.88289(14) 0.48386(11) 0.11940(14) 0.0231(4) Uani 1 1 d . . . N21 N 0.74383(14) 0.56566(11) 0.22443(13) 0.0226(4) Uani 1 1 d . . . N22 N 0.75201(14) 0.48389(11) 0.20708(13) 0.0232(4) Uani 1 1 d . . . N31 N 0.62997(14) 0.71837(11) 0.10050(12) 0.0208(4) Uani 1 1 d . . . N32 N 0.56669(14) 0.72663(11) 0.00796(13) 0.0221(4) Uani 1 1 d . . . N41 N 0.79004(14) 0.71551(11) -0.00671(12) 0.0219(4) Uani 1 1 d . . . N42 N 0.69795(14) 0.72467(12) -0.08011(13) 0.0230(4) Uani 1 1 d . . . C1 C 0.77661(17) 0.45620(14) 0.11950(16) 0.0239(5) Uani 1 1 d . . . H1 H 0.7764 0.3945 0.1193 0.029 Uiso 1 1 calc R . . C2 C 0.69182(17) 0.48556(14) 0.02992(16) 0.0229(5) Uani 1 1 d . . . C3 C 0.62997(17) 0.42932(15) -0.03538(17) 0.0263(5) Uani 1 1 d . . . H3 H 0.6402 0.3716 -0.0254 0.032 Uiso 1 1 calc R . . C4 C 0.55312(18) 0.45968(16) -0.11540(17) 0.0300(5) Uani 1 1 d . . . H4 H 0.5087 0.4228 -0.1606 0.036 Uiso 1 1 calc R . . C5 C 0.54140(17) 0.54406(15) -0.12913(16) 0.0266(5) Uani 1 1 d . . . H5 H 0.4898 0.5659 -0.1841 0.032 Uiso 1 1 calc R . . C6 C 0.60670(16) 0.59607(14) -0.06084(15) 0.0226(5) Uani 1 1 d . . . C7 C 0.59825(17) 0.68905(14) -0.07180(15) 0.0231(5) Uani 1 1 d . . . H7 H 0.5411 0.7015 -0.1330 0.028 Uiso 1 1 calc R . . C11 C 1.01040(17) 0.56959(14) 0.12857(15) 0.0230(5) Uani 1 1 d . . . H11 H 1.0493 0.6195 0.1300 0.028 Uiso 1 1 calc R . . C12 C 1.05629(17) 0.49064(14) 0.13604(15) 0.0227(5) Uani 1 1 d . . . C13 C 0.97255(17) 0.43743(14) 0.12947(15) 0.0228(5) Uani 1 1 d . . . H13 H 0.9764 0.3789 0.1316 0.027 Uiso 1 1 calc R . . C14 C 1.17177(18) 0.46932(16) 0.15027(19) 0.0324(5) Uani 1 1 d . . . H14a H 1.1770 0.4221 0.1093 0.049 Uiso 1 1 calc R . . H14b H 1.2049 0.4552 0.2183 0.049 Uiso 1 1 calc R . . H14c H 1.2091 0.5167 0.1325 0.049 Uiso 1 1 calc R . . C21 C 0.71639(19) 0.56937(15) 0.30661(17) 0.0291(5) Uani 1 1 d . . . H21 H 0.7057 0.6192 0.3374 0.035 Uiso 1 1 calc R . . C22 C 0.7053(2) 0.49024(16) 0.34216(19) 0.0379(6) Uani 1 1 d . . . C23 C 0.73040(19) 0.43727(15) 0.27740(17) 0.0306(5) Uani 1 1 d . . . H23 H 0.7323 0.3788 0.2812 0.037 Uiso 1 1 calc R . . C24 C 0.6732(4) 0.4689(2) 0.4316(3) 0.0716(12) Uani 1 1 d . . . H24a H 0.6694 0.4088 0.4373 0.107 Uiso 1 1 calc R . . H24b H 0.6028 0.4930 0.4274 0.107 Uiso 1 1 calc R . . H24c H 0.7264 0.4910 0.4886 0.107 Uiso 1 1 calc R . . C31 C 0.57639(17) 0.75631(13) 0.15472(16) 0.0220(5) Uani 1 1 d . . . H31 H 0.6015 0.7611 0.2232 0.026 Uiso 1 1 calc R . . C32 C 0.47838(17) 0.78823(14) 0.09838(16) 0.0249(5) Uani 1 1 d . . . C33 C 0.47524(17) 0.76776(13) 0.00481(16) 0.0235(5) Uani 1 1 d . . . H33 H 0.4190 0.7803 -0.0517 0.028 Uiso 1 1 calc R . . C34 C 0.3951(2) 0.83450(17) 0.13128(19) 0.0364(6) Uani 1 1 d . . . H34a H 0.3315 0.8427 0.0763 0.055 Uiso 1 1 calc R . . H34b H 0.4240 0.8882 0.1573 0.055 Uiso 1 1 calc R . . H34c H 0.3754 0.8028 0.1818 0.055 Uiso 1 1 calc R . . C41 C 0.86499(18) 0.75330(14) -0.03745(16) 0.0247(5) Uani 1 1 d . . . H41 H 0.9381 0.7571 -0.0009 0.030 Uiso 1 1 calc R . . C42 C 0.82349(19) 0.78710(15) -0.13039(17) 0.0282(5) Uani 1 1 d . . . C43 C 0.71612(19) 0.76710(15) -0.15530(16) 0.0280(5) Uani 1 1 d . . . H43 H 0.6642 0.7806 -0.2144 0.034 Uiso 1 1 calc R . . C44 C 0.8821(2) 0.83637(17) -0.1879(2) 0.0397(6) Uani 1 1 d . . . H44a H 0.8438 0.8327 -0.2569 0.060 Uiso 1 1 calc R . . H44b H 0.9549 0.8144 -0.1770 0.060 Uiso 1 1 calc R . . H44c H 0.8860 0.8942 -0.1673 0.060 Uiso 1 1 calc R . . Cl2 Cl 0.81907(4) 0.25556(3) 0.07796(4) 0.02608(13) Uani 1 1 d . . . O1S O 0.87745(14) 0.24224(11) -0.11345(13) 0.0342(4) Uani 1 1 d . . . H1S H 0.857(3) 0.2516(19) -0.063(2) 0.050(9) Uiso 1 1 d . . . C1S C 0.8922(2) 0.15684(17) -0.1246(2) 0.0395(6) Uani 1 1 d . . . H1Sa H 0.9452 0.1485 -0.1606 0.059 Uiso 1 1 calc R . . H1Sb H 0.8239 0.1318 -0.1603 0.059 Uiso 1 1 calc R . . H1Sc H 0.9178 0.1310 -0.0607 0.059 Uiso 1 1 calc R . . O2S O 0.4703(4) 0.9938(4) 0.0060(5) 0.0511(17) Uiso 0.348(3) 1 d P A -1 C2S C 0.5074(6) 1.0325(5) 0.0987(5) 0.0302(16) Uiso 0.348(3) 1 d P A -1 H2Sa H 0.5655 1.0720 0.0985 0.036 Uiso 0.348(3) 1 calc PR A -1 H2Sb H 0.5364 0.9904 0.1490 0.036 Uiso 0.348(3) 1 calc PR A -1 C3S C 0.4195(8) 1.0752(6) 0.1196(7) 0.050(2) Uiso 0.348(3) 1 d P A -1 H3Sa H 0.4447 1.1024 0.1828 0.075 Uiso 0.348(3) 1 calc PR A -1 H3Sb H 0.3629 1.0356 0.1210 0.075 Uiso 0.348(3) 1 calc PR A -1 H3Sc H 0.3911 1.1166 0.0694 0.075 Uiso 0.348(3) 1 calc PR A -1 C4S C 0.5580(7) 0.9644(6) -0.0253(6) 0.043(2) Uiso 0.348(3) 1 d P A -1 H4Sa H 0.5903 0.9157 0.0136 0.052 Uiso 0.348(3) 1 calc PR A -1 H4Sb H 0.6135 1.0078 -0.0163 0.052 Uiso 0.348(3) 1 calc PR A -1 C5S C 0.5200(7) 0.9419(6) -0.1272(6) 0.040(2) Uiso 0.348(3) 1 d P A -1 H5Sa H 0.5798 0.9197 -0.1486 0.060 Uiso 0.348(3) 1 calc PR A -1 H5Sb H 0.4909 0.9908 -0.1657 0.060 Uiso 0.348(3) 1 calc PR A -1 H5Sc H 0.4637 0.8999 -0.1360 0.060 Uiso 0.348(3) 1 calc PR A -1 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 0.01536(17) 0.01826(18) 0.01685(17) -0.00127(13) 0.00040(12) 0.00019(13) Cl1 0.0231(3) 0.0274(3) 0.0238(3) -0.0062(2) -0.0012(2) -0.0018(2) N9 0.0170(9) 0.0230(9) 0.0218(9) -0.0033(7) 0.0046(7) -0.0004(7) N11 0.0174(9) 0.0200(9) 0.0265(10) -0.0011(7) 0.0027(7) 0.0002(7) N12 0.0181(9) 0.0198(9) 0.0305(10) -0.0011(8) 0.0055(8) 0.0007(8) N21 0.0211(9) 0.0209(9) 0.0243(10) -0.0004(7) 0.0041(7) -0.0010(7) N22 0.0203(9) 0.0196(9) 0.0285(10) -0.0001(8) 0.0047(8) 0.0002(8) N31 0.0182(9) 0.0235(9) 0.0183(9) 0.0001(7) 0.0013(7) 0.0020(7) N32 0.0187(9) 0.0263(10) 0.0195(9) -0.0013(7) 0.0023(7) 0.0035(8) N41 0.0177(9) 0.0267(9) 0.0181(9) -0.0001(7) -0.0003(7) 0.0017(8) N42 0.0183(9) 0.0301(10) 0.0183(9) 0.0017(7) 0.0015(7) 0.0017(8) C1 0.0208(11) 0.0193(11) 0.0319(12) -0.0025(9) 0.0077(9) -0.0022(9) C2 0.0182(11) 0.0236(11) 0.0284(12) -0.0044(9) 0.0093(9) -0.0011(9) C3 0.0208(11) 0.0272(12) 0.0336(13) -0.0093(10) 0.0123(10) -0.0050(10) C4 0.0205(11) 0.0396(14) 0.0311(13) -0.0164(10) 0.0095(10) -0.0100(10) C5 0.0152(10) 0.0407(14) 0.0230(12) -0.0072(10) 0.0040(9) -0.0031(10) C6 0.0149(10) 0.0312(12) 0.0232(11) -0.0062(9) 0.0076(8) 0.0003(9) C7 0.0175(11) 0.0310(12) 0.0184(11) -0.0010(9) 0.0013(8) 0.0026(9) C11 0.0204(11) 0.0264(11) 0.0222(11) -0.0010(9) 0.0060(9) -0.0033(9) C12 0.0188(11) 0.0292(12) 0.0204(11) -0.0015(9) 0.0058(8) 0.0013(9) C13 0.0230(11) 0.0226(11) 0.0221(11) 0.0003(9) 0.0051(9) 0.0055(9) C14 0.0229(12) 0.0337(13) 0.0426(14) -0.0006(11) 0.0124(10) 0.0040(10) C21 0.0315(13) 0.0297(12) 0.0271(12) -0.0045(10) 0.0095(10) -0.0060(10) C22 0.0486(16) 0.0332(14) 0.0351(14) -0.0004(11) 0.0172(12) -0.0116(12) C23 0.0306(13) 0.0249(12) 0.0342(13) 0.0044(10) 0.0057(10) -0.0044(10) C24 0.128(3) 0.0481(19) 0.056(2) -0.0020(16) 0.055(2) -0.026(2) C31 0.0235(11) 0.0218(11) 0.0203(11) -0.0016(8) 0.0053(9) -0.0012(9) C32 0.0204(11) 0.0263(12) 0.0272(12) -0.0044(9) 0.0052(9) -0.0012(9) C33 0.0159(10) 0.0262(11) 0.0259(11) -0.0002(9) 0.0018(9) 0.0033(9) C34 0.0282(13) 0.0451(15) 0.0352(14) -0.0071(11) 0.0080(11) 0.0068(12) C41 0.0216(11) 0.0245(11) 0.0270(12) -0.0009(9) 0.0050(9) -0.0006(9) C42 0.0281(12) 0.0316(12) 0.0261(12) 0.0034(10) 0.0092(10) 0.0026(10) C43 0.0293(12) 0.0343(13) 0.0193(11) 0.0051(9) 0.0048(9) 0.0039(10) C44 0.0412(15) 0.0430(15) 0.0376(15) 0.0126(12) 0.0152(12) -0.0021(13) Cl2 0.0311(3) 0.0231(3) 0.0241(3) -0.0011(2) 0.0080(2) 0.0007(2) O1S 0.0363(10) 0.0419(10) 0.0266(9) -0.0031(7) 0.0127(8) -0.0043(8) C1S 0.0357(14) 0.0449(16) 0.0394(15) -0.0077(12) 0.0132(12) -0.0049(12) _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 Cl1 2.3230(6) . ? Fe1 N9 2.2682(17) . ? Fe1 N11 2.1691(18) . ? Fe1 N21 2.1849(18) . ? Fe1 N31 2.1820(18) . ? Fe1 N41 2.1746(18) . ? N9 C2 1.342(3) . ? N9 C6 1.341(3) . ? N11 C11 1.334(3) . ? N12 N11 1.361(2) . ? N12 C1 1.452(3) . ? N12 C13 1.360(3) . ? N21 C21 1.328(3) . ? N22 N21 1.359(3) . ? N22 C1 1.455(3) . ? N22 C23 1.353(3) . ? N31 C31 1.332(3) . ? N32 N31 1.361(2) . ? N32 C7 1.456(3) . ? N32 C33 1.352(3) . ? N41 C41 1.326(3) . ? N42 N41 1.364(2) . ? N42 C7 1.453(3) . ? N42 C43 1.357(3) . ? C1 H1 1.0000 . ? C2 C1 1.518(3) . ? C2 C3 1.391(3) . ? C3 H3 0.9500 . ? C3 C4 1.386(3) . ? C4 H4 0.9500 . ? C4 C5 1.384(3) . ? C5 H5 0.9500 . ? C5 C6 1.389(3) . ? C6 C7 1.516(3) . ? C7 H7 1.0000 . ? C11 H11 0.9500 . ? C12 C11 1.403(3) . ? C12 C14 1.496(3) . ? C13 C12 1.371(3) . ? C13 H13 0.9500 . ? C14 H14a 0.9800 . ? C14 H14b 0.9800 . ? C14 H14c 0.9800 . ? C21 H21 0.9500 . ? C22 C21 1.403(4) . ? C22 C24 1.499(4) . ? C23 C22 1.372(4) . ? C23 H23 0.9500 . ? C24 H24a 0.9800 . ? C24 H24b 0.9800 . ? C24 H24c 0.9800 . ? C31 H31 0.9500 . ? C32 C31 1.402(3) . ? C32 C34 1.498(3) . ? C33 C32 1.376(3) . ? C33 H33 0.9500 . ? C34 H34a 0.9800 . ? C34 H34b 0.9800 . ? C34 H34c 0.9800 . ? C41 H41 0.9500 . ? C42 C41 1.405(3) . ? C42 C44 1.501(3) . ? C43 C42 1.378(3) . ? C43 H43 0.9500 . ? C44 H44a 0.9800 . ? C44 H44b 0.9800 . ? C44 H44c 0.9800 . ? O1S H1S 0.85(3) . ? O1S C1S 1.413(3) . ? C1S H1Sa 0.9800 . ? C1S H1Sb 0.9800 . ? C1S H1Sc 0.9800 . ? O2S C2S 1.429(10) . ? O2S C4S 1.419(12) . ? C2S H2Sa 0.9900 . ? C2S H2Sb 0.9900 . ? C2S C3S 1.437(12) . ? C3S H3Sa 0.9800 . ? C3S H3Sb 0.9800 . ? C3S H3Sc 0.9800 . ? C4S H4Sa 0.9900 . ? C4S H4Sb 0.9900 . ? C4S C5S 1.456(12) . ? C5S H5Sa 0.9800 . ? C5S H5Sb 0.9800 . ? C5S H5Sc 0.9800 . ? 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 N9 Fe1 Cl1 177.98(5) . . ? N11 Fe1 Cl1 97.95(5) . . ? N11 Fe1 N9 80.94(6) . . ? N11 Fe1 N21 83.90(7) . . ? N11 Fe1 N31 161.38(7) . . ? N11 Fe1 N41 92.75(7) . . ? N21 Fe1 Cl1 101.89(5) . . ? N21 Fe1 N9 79.71(7) . . ? N31 Fe1 Cl1 100.65(5) . . ? N31 Fe1 N9 80.44(6) . . ? N31 Fe1 N21 92.89(7) . . ? N41 Fe1 Cl1 98.11(5) . . ? N41 Fe1 N9 80.29(7) . . ? N41 Fe1 N21 159.99(7) . . ? N41 Fe1 N31 83.99(7) . . ? C2 N9 Fe1 120.56(14) . . ? C6 N9 Fe1 120.69(15) . . ? C6 N9 C2 118.75(19) . . ? N12 N11 Fe1 119.68(13) . . ? C11 N11 Fe1 134.51(15) . . ? C11 N11 N12 104.94(17) . . ? N11 N12 C1 120.41(17) . . ? C13 N12 N11 111.29(17) . . ? C13 N12 C1 127.95(19) . . ? N22 N21 Fe1 119.19(14) . . ? C21 N21 Fe1 135.50(16) . . ? C21 N21 N22 105.18(18) . . ? N21 N22 C1 120.50(18) . . ? C23 N22 N21 111.36(19) . . ? C23 N22 C1 128.08(19) . . ? N32 N31 Fe1 119.30(13) . . ? C31 N31 Fe1 135.85(14) . . ? C31 N31 N32 104.82(17) . . ? N31 N32 C7 120.23(17) . . ? C33 N32 N31 111.44(17) . . ? C33 N32 C7 128.22(18) . . ? N42 N41 Fe1 119.50(13) . . ? C41 N41 Fe1 135.41(15) . . ? C41 N41 N42 104.94(17) . . ? N41 N42 C7 120.10(17) . . ? C43 N42 N41 111.21(18) . . ? C43 N42 C7 128.67(19) . . ? N12 C1 N22 110.18(17) . . ? N12 C1 H1 108.1 . . ? N12 C1 C2 111.48(18) . . ? N22 C1 H1 108.1 . . ? N22 C1 C2 110.82(18) . . ? C2 C1 H1 108.1 . . ? N9 C2 C1 116.75(18) . . ? N9 C2 C3 122.5(2) . . ? C3 C2 C1 120.8(2) . . ? C2 C3 H3 120.9 . . ? C4 C3 C2 118.3(2) . . ? C4 C3 H3 120.9 . . ? C3 C4 H4 120.2 . . ? C5 C4 C3 119.6(2) . . ? C5 C4 H4 120.2 . . ? C4 C5 H5 120.7 . . ? C4 C5 C6 118.6(2) . . ? C6 C5 H5 120.7 . . ? N9 C6 C5 122.3(2) . . ? N9 C6 C7 116.47(18) . . ? C5 C6 C7 121.2(2) . . ? N32 C7 C6 111.24(18) . . ? N32 C7 H7 107.8 . . ? N42 C7 N32 110.64(18) . . ? N42 C7 C6 111.31(18) . . ? N42 C7 H7 107.8 . . ? C6 C7 H7 107.8 . . ? N11 C11 H11 124.2 . . ? N11 C11 C12 111.52(19) . . ? C12 C11 H11 124.2 . . ? C11 C12 C14 127.5(2) . . ? C13 C12 C11 104.89(19) . . ? C13 C12 C14 127.6(2) . . ? N12 C13 C12 107.36(19) . . ? N12 C13 H13 126.3 . . ? C12 C13 H13 126.3 . . ? C12 C14 H14a 109.5 . . ? C12 C14 H14b 109.5 . . ? C12 C14 H14c 109.5 . . ? H14a C14 H14b 109.5 . . ? H14a C14 H14c 109.5 . . ? H14b C14 H14c 109.5 . . ? N21 C21 H21 124.3 . . ? N21 C21 C22 111.3(2) . . ? C22 C21 H21 124.3 . . ? C21 C22 C24 127.2(3) . . ? C23 C22 C21 104.9(2) . . ? C23 C22 C24 127.9(3) . . ? N22 C23 C22 107.3(2) . . ? N22 C23 H23 126.4 . . ? C22 C23 H23 126.4 . . ? C22 C24 H24a 109.5 . . ? C22 C24 H24b 109.5 . . ? C22 C24 H24c 109.5 . . ? H24a C24 H24b 109.5 . . ? H24a C24 H24c 109.5 . . ? H24b C24 H24c 109.5 . . ? N31 C31 H31 124.1 . . ? N31 C31 C32 111.74(19) . . ? C32 C31 H31 124.1 . . ? C31 C32 C34 128.4(2) . . ? C33 C32 C31 104.5(2) . . ? C33 C32 C34 127.1(2) . . ? N32 C33 C32 107.52(19) . . ? N32 C33 H33 126.2 . . ? C32 C33 H33 126.2 . . ? C32 C34 H34a 109.5 . . ? C32 C34 H34b 109.5 . . ? C32 C34 H34c 109.5 . . ? H34a C34 H34b 109.5 . . ? H34a C34 H34c 109.5 . . ? H34b C34 H34c 109.5 . . ? N41 C41 H41 124.0 . . ? N41 C41 C42 112.1(2) . . ? C42 C41 H41 124.0 . . ? C41 C42 C44 127.8(2) . . ? C43 C42 C41 104.3(2) . . ? C43 C42 C44 127.9(2) . . ? N42 C43 C42 107.5(2) . . ? N42 C43 H43 126.2 . . ? C42 C43 H43 126.2 . . ? C42 C44 H44a 109.5 . . ? C42 C44 H44b 109.5 . . ? C42 C44 H44c 109.5 . . ? H44a C44 H44b 109.5 . . ? H44a C44 H44c 109.5 . . ? H44b C44 H44c 109.5 . . ? C1S O1S H1S 111(2) . . ? O1S C1S H1Sa 109.5 . . ? O1S C1S H1Sb 109.5 . . ? O1S C1S H1Sc 109.5 . . ? H1Sa C1S H1Sb 109.5 . . ? H1Sa C1S H1Sc 109.5 . . ? H1Sb C1S H1Sc 109.5 . . ? C4S O2S C2S 110.7(6) . . ? O2S C2S H2Sa 109.9 . . ? O2S C2S H2Sb 109.9 . . ? O2S C2S C3S 109.1(6) . . ? H2Sa C2S H2Sb 108.3 . . ? C3S C2S H2Sa 109.9 . . ? C3S C2S H2Sb 109.9 . . ? C2S C3S H3Sa 109.5 . . ? C2S C3S H3Sb 109.5 . . ? C2S C3S H3Sc 109.5 . . ? H3Sa C3S H3Sb 109.5 . . ? H3Sa C3S H3Sc 109.5 . . ? H3Sb C3S H3Sc 109.5 . . ? O2S C4S H4Sa 109.8 . . ? O2S C4S H4Sb 109.8 . . ? O2S C4S C5S 109.2(7) . . ? H4Sa C4S H4Sb 108.3 . . ? C5S C4S H4Sa 109.8 . . ? C5S C4S H4Sb 109.8 . . ? C4S C5S H5Sa 109.5 . . ? C4S C5S H5Sb 109.5 . . ? C4S C5S H5Sc 109.5 . . ? H5Sa C5S H5Sb 109.5 . . ? H5Sa C5S H5Sc 109.5 . . ? H5Sb C5S H5Sc 109.5 . . ? 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 O1S H1S Cl2 0.85(3) 2.22(3) 3.0613(19) 170(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 Fe1 N9 C2 C1 0.4(3) . . . . ? Fe1 N9 C2 C3 -179.80(16) . . . . ? Fe1 N9 C6 C5 -179.85(16) . . . . ? Fe1 N9 C6 C7 0.1(2) . . . . ? Fe1 N11 C11 C12 168.11(15) . . . . ? Fe1 N21 C21 C22 -176.44(17) . . . . ? Fe1 N31 C31 C32 178.77(16) . . . . ? Fe1 N41 C41 C42 -175.66(16) . . . . ? Cl1 Fe1 N9 C2 98.7(14) . . . . ? Cl1 Fe1 N9 C6 -80.3(14) . . . . ? Cl1 Fe1 N11 N12 138.16(14) . . . . ? Cl1 Fe1 N11 C11 -29.4(2) . . . . ? Cl1 Fe1 N21 N22 -132.35(14) . . . . ? Cl1 Fe1 N21 C21 42.8(2) . . . . ? Cl1 Fe1 N31 N32 133.79(14) . . . . ? Cl1 Fe1 N31 C31 -44.1(2) . . . . ? Cl1 Fe1 N41 N42 -136.33(15) . . . . ? Cl1 Fe1 N41 C41 38.7(2) . . . . ? N9 Fe1 N11 N12 -43.54(15) . . . . ? N9 Fe1 N11 C11 148.9(2) . . . . ? N9 Fe1 N21 N22 46.39(14) . . . . ? N9 Fe1 N21 C21 -138.4(2) . . . . ? N9 Fe1 N31 N32 -44.49(15) . . . . ? N9 Fe1 N31 C31 137.7(2) . . . . ? N9 Fe1 N41 N42 44.91(15) . . . . ? N9 Fe1 N41 C41 -140.1(2) . . . . ? N9 C2 C1 N12 -61.5(3) . . . . ? N9 C2 C1 N22 61.6(2) . . . . ? N9 C2 C3 C4 -0.4(3) . . . . ? N9 C6 C7 N32 -62.1(2) . . . . ? N9 C6 C7 N42 61.8(2) . . . . ? N11 Fe1 N9 C2 41.78(16) . . . . ? N11 Fe1 N9 C6 -137.26(16) . . . . ? N11 Fe1 N21 N22 -35.48(15) . . . . ? N11 Fe1 N21 C21 139.7(2) . . . . ? N11 Fe1 N31 N32 -44.1(3) . . . . ? N11 Fe1 N31 C31 138.1(2) . . . . ? N11 Fe1 N41 N42 125.23(16) . . . . ? N11 Fe1 N41 C41 -59.8(2) . . . . ? N11 N12 C1 N22 -62.4(3) . . . . ? N11 N12 C1 C2 61.0(3) . . . . ? N11 N12 C13 C12 0.0(2) . . . . ? N12 N11 C11 C12 -0.7(2) . . . . ? N12 C13 C12 C11 -0.4(2) . . . . ? N12 C13 C12 C14 178.4(2) . . . . ? N21 Fe1 N9 C2 -43.61(16) . . . . ? N21 Fe1 N9 C6 137.35(16) . . . . ? N21 Fe1 N11 N12 36.96(15) . . . . ? N21 Fe1 N11 C11 -130.6(2) . . . . ? N21 Fe1 N31 N32 -123.54(15) . . . . ? N21 Fe1 N31 C31 58.6(2) . . . . ? N21 Fe1 N41 N42 45.5(3) . . . . ? N21 Fe1 N41 C41 -139.5(2) . . . . ? N21 N22 C1 N12 64.1(2) . . . . ? N21 N22 C1 C2 -59.7(2) . . . . ? N21 N22 C23 C22 1.1(3) . . . . ? N22 N21 C21 C22 -0.8(3) . . . . ? N22 C23 C22 C21 -1.5(3) . . . . ? N22 C23 C22 C24 178.7(3) . . . . ? N31 Fe1 N9 C2 -138.35(17) . . . . ? N31 Fe1 N9 C6 42.61(16) . . . . ? N31 Fe1 N11 N12 -43.9(3) . . . . ? N31 Fe1 N11 C11 148.5(2) . . . . ? N31 Fe1 N21 N22 126.12(15) . . . . ? N31 Fe1 N21 C21 -58.7(2) . . . . ? N31 Fe1 N41 N42 -36.38(15) . . . . ? N31 Fe1 N41 C41 138.6(2) . . . . ? N31 N32 C7 N42 -63.1(2) . . . . ? N31 N32 C7 C6 61.2(2) . . . . ? N31 N32 C33 C32 0.6(3) . . . . ? N32 N31 C31 C32 0.7(2) . . . . ? N32 C33 C32 C31 -0.1(2) . . . . ? N32 C33 C32 C34 179.7(2) . . . . ? N41 Fe1 N9 C2 136.18(17) . . . . ? N41 Fe1 N9 C6 -42.87(16) . . . . ? N41 Fe1 N11 N12 -123.25(15) . . . . ? N41 Fe1 N11 C11 69.2(2) . . . . ? N41 Fe1 N21 N22 45.8(3) . . . . ? N41 Fe1 N21 C21 -139.1(2) . . . . ? N41 Fe1 N31 N32 36.63(15) . . . . ? N41 Fe1 N31 C31 -141.2(2) . . . . ? N41 N42 C7 N32 63.4(2) . . . . ? N41 N42 C7 C6 -60.8(2) . . . . ? N41 N42 C43 C42 -0.5(3) . . . . ? N42 N41 C41 C42 -0.2(3) . . . . ? N42 C43 C42 C41 0.3(3) . . . . ? N42 C43 C42 C44 -177.7(2) . . . . ? C1 N12 N11 Fe1 3.4(3) . . . . ? C1 N12 N11 C11 174.19(19) . . . . ? C1 N12 C13 C12 -173.2(2) . . . . ? C1 N22 N21 Fe1 -6.2(2) . . . . ? C1 N22 N21 C21 177.28(19) . . . . ? C1 N22 C23 C22 -176.1(2) . . . . ? C1 C2 C3 C4 179.4(2) . . . . ? C2 N9 C6 C5 1.1(3) . . . . ? C2 N9 C6 C7 -178.93(18) . . . . ? C2 C3 C4 C5 1.2(3) . . . . ? C3 C2 C1 N12 118.7(2) . . . . ? C3 C2 C1 N22 -118.2(2) . . . . ? C3 C4 C5 C6 -0.9(3) . . . . ? C4 C5 C6 N9 -0.3(3) . . . . ? C4 C5 C6 C7 179.7(2) . . . . ? C5 C6 C7 N32 117.9(2) . . . . ? C5 C6 C7 N42 -118.2(2) . . . . ? C6 N9 C2 C1 179.43(18) . . . . ? C6 N9 C2 C3 -0.7(3) . . . . ? C7 N32 N31 Fe1 4.1(2) . . . . ? C7 N32 N31 C31 -177.41(19) . . . . ? C7 N32 C33 C32 176.9(2) . . . . ? C7 N42 N41 Fe1 -4.7(3) . . . . ? C7 N42 N41 C41 178.96(19) . . . . ? C7 N42 C43 C42 -178.9(2) . . . . ? C13 N12 N11 Fe1 -170.41(14) . . . . ? C13 N12 N11 C11 0.4(2) . . . . ? C13 N12 C1 N22 110.2(2) . . . . ? C13 N12 C1 C2 -126.3(2) . . . . ? C13 C12 C11 N11 0.7(2) . . . . ? C14 C12 C11 N11 -178.1(2) . . . . ? C23 N22 N21 Fe1 176.30(14) . . . . ? C23 N22 N21 C21 -0.2(2) . . . . ? C23 N22 C1 N12 -118.9(2) . . . . ? C23 N22 C1 C2 117.3(2) . . . . ? C23 C22 C21 N21 1.5(3) . . . . ? C24 C22 C21 N21 -178.7(3) . . . . ? C33 N32 N31 Fe1 -179.26(14) . . . . ? C33 N32 N31 C31 -0.8(2) . . . . ? C33 N32 C7 N42 120.9(2) . . . . ? C33 N32 C7 C6 -114.8(2) . . . . ? C33 C32 C31 N31 -0.4(3) . . . . ? C34 C32 C31 N31 179.8(2) . . . . ? C43 N42 N41 Fe1 176.75(15) . . . . ? C43 N42 N41 C41 0.4(2) . . . . ? C43 N42 C7 N32 -118.3(2) . . . . ? C43 N42 C7 C6 117.5(2) . . . . ? C43 C42 C41 N41 -0.1(3) . . . . ? C44 C42 C41 N41 177.9(2) . . . . ? C2S O2S C4S C5S -167.8(7) . . . . ? C4S O2S C2S C3S 169.0(7) . . . . ? #===END data_3x2MeOH_gard4ha _database_code_depnum_ccdc_archive 'CCDC 821760' #TrackingRef '- FeClpzR4lutCl_06022011.cif' _audit_creation_date 2011-05-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C13.5 H16.5 Cl0.5 Fe0.5 N4.5), Cl, 2(C H4 O)' _chemical_formula_sum 'C29 H41 Cl2 Fe N9 O2' _chemical_formula_weight 674.46 _chemical_melting_point ? 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' _space_group_crystal_system orthorhombic _space_group_IT_number 62 _space_group_name_H-M_alt 'P n m a' _space_group_name_Hall '-P 2ac 2n' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z' 4 'x+1/2, -y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z' 8 '-x-1/2, y-1/2, z-1/2' _cell_length_a 14.3222(2) _cell_length_b 12.9169(2) _cell_length_c 17.1494(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3172.61(8) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5682 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 66 _cell_measurement_theta_min 4 _exptl_absorpt_coefficient_mu 5.709 _exptl_absorpt_correction_T_max 0.6580 _exptl_absorpt_correction_T_min 0.2203 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.412 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1416 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_unetI/netI 0.0249 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 26706 _diffrn_reflns_theta_full 67.13 _diffrn_reflns_theta_max 67.13 _diffrn_reflns_theta_min 4.02 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2686 _reflns_number_total 2919 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_collection 'APEX2 v2.0-2 (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _refine_diff_density_max 0.504 _refine_diff_density_min -0.273 _refine_diff_density_rms 0.053 _refine_ls_extinction_coef 0.00018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 300 _refine_ls_number_reflns 2919 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0352 _refine_ls_restrained_S_all 1.063 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0284P)^2^+4.1313P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0775 _refine_ls_wR_factor_ref 0.0790 _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. The hydrogen atoms of solvent molecules were put in geometrically calculated positions with Uiso = 1.5 Uiso/eq of an adjacent atom and refined within a riding model using appropriate fixed distances to the adjacent atoms. Theirpositions were also optimized rotationally to fit the residual electron density ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.65606(3) 0.2500 0.39005(3) 0.01177(14) Uani 1 2 d S . . Cl1 Cl 0.81632(5) 0.2500 0.41281(4) 0.01721(18) Uani 1 2 d S . . N1 N 0.50218(17) 0.2500 0.37549(14) 0.0125(5) Uani 1 2 d S . . N11 N 0.62053(12) 0.13504(14) 0.48366(10) 0.0139(4) Uani 1 1 d . . . N12 N 0.54604(12) 0.15724(14) 0.53151(10) 0.0129(4) Uani 1 1 d . . . N41 N 0.65242(12) 0.14079(14) 0.28286(10) 0.0151(4) Uani 1 1 d . . . N42 N 0.58220(12) 0.15710(15) 0.22930(10) 0.0183(4) Uani 1 1 d . . . C1 C 0.4913(2) 0.2500 0.51841(17) 0.0133(6) Uani 1 2 d S . . H1 H 0.440(2) 0.2500 0.5567(17) 0.014(7) Uiso 1 2 d S . . C2 C 0.4457(2) 0.2500 0.43840(17) 0.0120(6) Uani 1 2 d S . . C3 C 0.3493(2) 0.2500 0.43299(19) 0.0143(6) Uani 1 2 d S . . H3 H 0.312(2) 0.2500 0.4821(19) 0.017(8) Uiso 1 2 d S . . C4 C 0.3083(2) 0.2500 0.35992(19) 0.0143(6) Uani 1 2 d S . . H4 H 0.243(3) 0.2500 0.355(2) 0.024(10) Uiso 1 2 d S . . C5 C 0.3655(2) 0.2500 0.29467(18) 0.0147(7) Uani 1 2 d S . . H5 H 0.339(2) 0.2500 0.2426(19) 0.016(8) Uiso 1 2 d S . . C6 C 0.4616(2) 0.2500 0.30464(17) 0.0131(6) Uani 1 2 d S . . C7 C 0.5248(2) 0.2500 0.23394(18) 0.0169(7) Uani 1 2 d S . . H7 H 0.486(2) 0.2500 0.186(2) 0.017(9) Uiso 1 2 d S . . C10 C 0.74366(18) -0.0016(2) 0.48330(14) 0.0204(5) Uani 1 1 d . . . H10a H 0.785(2) 0.041(2) 0.4677(16) 0.030(8) Uiso 1 1 d . . . H10b H 0.7306(19) -0.046(2) 0.4364(17) 0.039(8) Uiso 1 1 d . . . H10c H 0.7726(19) -0.044(2) 0.5227(16) 0.032(7) Uiso 1 1 d . . . C11 C 0.65841(15) 0.04938(17) 0.51512(12) 0.0150(5) Uani 1 1 d . . . C12 C 0.60777(16) 0.01838(17) 0.58082(12) 0.0164(5) Uani 1 1 d . . . H12 H 0.6200(15) -0.0382(19) 0.6119(13) 0.011(6) Uiso 1 1 d . . . C13 C 0.53752(15) 0.08840(17) 0.59107(12) 0.0154(5) Uani 1 1 d . . . C14 C 0.46728(17) 0.0965(2) 0.65475(14) 0.0211(5) Uani 1 1 d . . . H14a H 0.4654(18) 0.026(2) 0.6831(15) 0.031(7) Uiso 1 1 d . . . H14b H 0.407(2) 0.114(2) 0.6363(16) 0.037(8) Uiso 1 1 d . . . H14c H 0.484(3) 0.149(3) 0.687(2) 0.071(12) Uiso 1 1 d . . . C40 C 0.78690(18) 0.0189(2) 0.29155(14) 0.0220(5) Uani 1 1 d . . . H40a H 0.8088(16) 0.0631(19) 0.3344(14) 0.014(6) Uiso 1 1 d . . . H40b H 0.8366(19) 0.016(2) 0.2540(17) 0.032(7) Uiso 1 1 d . . . H40c H 0.7733(19) -0.049(2) 0.3132(16) 0.032(7) Uiso 1 1 d . . . C41 C 0.70115(15) 0.06112(17) 0.25376(13) 0.0162(5) Uani 1 1 d . . . C42 C 0.66164(16) 0.0270(2) 0.18383(14) 0.0222(5) Uani 1 1 d . . . H42 H 0.6820(16) -0.027(2) 0.1546(14) 0.018(6) Uiso 1 1 d . . . C43 C 0.58735(16) 0.0886(2) 0.16860(13) 0.0250(6) Uani 1 1 d . . . C44 C 0.5217(2) 0.0890(4) 0.1009(2) 0.0511(11) Uani 1 1 d . . . H44a H 0.461(2) 0.097(3) 0.1135(17) 0.046(9) Uiso 1 1 d . . . H44b H 0.531(3) 0.031(3) 0.072(2) 0.072(12) Uiso 1 1 d . . . H44c H 0.536(3) 0.147(3) 0.066(2) 0.070(14) Uiso 1 1 d . . . Cl2 Cl 0.25353(5) 0.2500 0.62452(5) 0.02083(19) Uani 1 2 d S . . O1S O 0.1477(2) 0.2500 0.78532(19) 0.0542(9) Uani 1 2 d S . . H1S H 0.177(4) 0.2500 0.737(3) 0.065 Uiso 1 2 d S . . C1S C 0.2259(3) 0.2500 0.8348(2) 0.0331(9) Uani 1 2 d S . . H1Sa H 0.2388 0.3209 0.8521 0.050 Uiso 0.50 1 calc PR . . H1Sb H 0.2802 0.2230 0.8065 0.050 Uiso 0.50 1 calc PR . . H1Sc H 0.2133 0.2062 0.8802 0.050 Uiso 0.50 1 calc PR . . O2S O 0.0583(3) 0.2095(4) 0.5518(3) 0.071(2) Uani 0.50 1 d P A -1 H2S H 0.1124 0.2155 0.5701 0.107 Uiso 0.50 1 calc PR A -1 C2S C -0.0077(4) 0.265(3) 0.6015(3) 0.053(6) Uani 0.50 1 d P A -1 H2Sa H -0.0199 0.2242 0.6487 0.080 Uiso 0.50 1 calc PR A -1 H2Sb H -0.0663 0.2757 0.5731 0.080 Uiso 0.50 1 calc PR A -1 H2Sc H 0.0188 0.3322 0.6162 0.080 Uiso 0.50 1 calc PR A -1 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 0.0096(3) 0.0143(3) 0.0114(2) 0.000 -0.00007(18) 0.000 Cl1 0.0105(4) 0.0214(4) 0.0197(4) 0.000 -0.0002(3) 0.000 N1 0.0131(13) 0.0116(12) 0.0129(12) 0.000 0.0012(10) 0.000 N11 0.0131(9) 0.0160(9) 0.0126(9) 0.0003(7) 0.0005(7) 0.0001(8) N12 0.0129(9) 0.0127(9) 0.0130(9) 0.0013(7) 0.0022(7) 0.0008(7) N41 0.0140(9) 0.0171(9) 0.0143(9) 0.0011(8) 0.0014(7) -0.0018(8) N42 0.0120(9) 0.0270(11) 0.0159(9) -0.0053(8) -0.0007(7) 0.0003(8) C1 0.0123(15) 0.0139(15) 0.0139(15) 0.000 0.0012(13) 0.000 C2 0.0140(15) 0.0080(14) 0.0140(15) 0.000 0.0006(12) 0.000 C3 0.0141(16) 0.0106(15) 0.0183(16) 0.000 0.0037(13) 0.000 C4 0.0098(15) 0.0120(15) 0.0212(16) 0.000 -0.0007(13) 0.000 C5 0.0149(16) 0.0138(15) 0.0156(16) 0.000 -0.0022(13) 0.000 C6 0.0137(16) 0.0098(15) 0.0157(15) 0.000 0.0002(12) 0.000 C7 0.0114(15) 0.0257(18) 0.0136(15) 0.000 -0.0010(13) 0.000 C10 0.0238(13) 0.0190(12) 0.0183(12) 0.0034(11) 0.0021(10) 0.0050(11) C11 0.0170(11) 0.0147(11) 0.0134(10) -0.0034(9) -0.0021(9) -0.0010(9) C12 0.0209(12) 0.0132(11) 0.0149(11) 0.0019(9) -0.0032(9) -0.0005(9) C13 0.0163(11) 0.0175(11) 0.0123(10) 0.0017(9) -0.0019(9) -0.0051(9) C14 0.0206(13) 0.0244(14) 0.0183(12) 0.0047(11) 0.0046(10) 0.0011(10) C40 0.0276(14) 0.0227(13) 0.0158(12) 0.0029(10) 0.0043(10) 0.0063(11) C41 0.0165(11) 0.0148(11) 0.0173(11) 0.0001(9) 0.0071(9) -0.0028(9) C42 0.0187(12) 0.0253(13) 0.0225(12) -0.0104(11) 0.0075(10) -0.0022(10) C43 0.0168(12) 0.0390(15) 0.0192(12) -0.0144(11) 0.0035(10) -0.0019(11) C44 0.0228(16) 0.092(3) 0.0384(18) -0.042(2) -0.0114(14) 0.0218(18) Cl2 0.0241(4) 0.0176(4) 0.0207(4) 0.000 0.0075(3) 0.000 O1S 0.0394(18) 0.086(3) 0.0370(17) 0.000 0.0133(14) 0.000 C1S 0.042(2) 0.026(2) 0.032(2) 0.000 0.0119(18) 0.000 O2S 0.054(3) 0.116(6) 0.044(3) -0.024(3) -0.017(2) 0.009(3) C2S 0.045(3) 0.076(19) 0.040(3) -0.001(5) 0.001(2) 0.003(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 Fe1 Cl1 2.3282(9) . ? Fe1 N1 2.218(3) . ? Fe1 N11 2.2453(18) . ? Fe1 N11 2.2453(18) 7_565 ? Fe1 N41 2.3177(18) . ? Fe1 N41 2.3178(18) 7_565 ? N1 C2 1.348(4) . ? N1 C6 1.347(4) . ? N11 C11 1.345(3) . ? N12 N11 1.376(2) . ? N12 C1 1.449(2) . ? N12 C13 1.360(3) . ? N41 C41 1.340(3) . ? N42 N41 1.378(2) . ? N42 C7 1.456(3) . ? N42 C43 1.368(3) . ? C1 N12 1.449(2) 7_565 ? C1 H1 0.99(3) . ? C2 C1 1.520(4) . ? C3 C2 1.385(4) . ? C3 H3 1.00(3) . ? C4 C3 1.383(5) . ? C4 H4 0.94(4) . ? C5 C4 1.387(4) . ? C5 H5 0.97(3) . ? C6 C5 1.387(4) . ? C6 C7 1.513(4) . ? C7 N42 1.456(3) 7_565 ? C7 H7 1.00(3) . ? C10 H10a 0.84(3) . ? C10 H10b 1.01(3) . ? C10 H10c 0.97(3) . ? C11 C10 1.491(3) . ? C12 C11 1.398(3) . ? C12 H12 0.92(2) . ? C13 C12 1.364(3) . ? C13 C14 1.489(3) . ? C14 H14a 1.04(3) . ? C14 H14b 0.95(3) . ? C14 H14c 0.91(4) . ? C40 H40a 0.98(2) . ? C40 H40b 0.96(3) . ? C40 H40c 0.97(3) . ? C41 C40 1.492(3) . ? C42 C41 1.397(3) . ? C42 H42 0.91(3) . ? C43 C42 1.354(4) . ? C43 C44 1.493(4) . ? C44 H44a 0.90(3) . ? C44 H44b 0.90(4) . ? C44 H44c 0.98(4) . ? O1S H1S 0.93(5) . ? O1S C1S 1.405(5) . ? C1S H1Sa 0.9800 . ? C1S H1Sb 0.9800 . ? C1S H1Sc 0.9800 . ? O2S H2S 0.8400 . ? O2S C2S 1.461(19) . ? C2S H2Sa 0.9800 . ? C2S H2Sb 0.9800 . ? C2S H2Sc 0.9800 . ? 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 N1 Fe1 Cl1 176.82(7) . . ? N1 Fe1 N11 81.68(7) . . ? N1 Fe1 N11 81.68(7) . 7_565 ? N1 Fe1 N41 83.59(7) . . ? N1 Fe1 N41 83.59(7) . 7_565 ? N11 Fe1 Cl1 95.95(5) 7_565 . ? N11 Fe1 Cl1 95.95(5) . . ? N11 Fe1 N11 82.81(9) . 7_565 ? N11 Fe1 N41 164.69(7) . 7_565 ? N11 Fe1 N41 164.69(7) 7_565 . ? N11 Fe1 N41 99.18(6) 7_565 7_565 ? N11 Fe1 N41 99.18(6) . . ? N41 Fe1 Cl1 98.92(5) . . ? N41 Fe1 Cl1 98.92(5) 7_565 . ? N41 Fe1 N41 74.98(9) . 7_565 ? C2 N1 Fe1 120.4(2) . . ? C6 N1 Fe1 122.0(2) . . ? C6 N1 C2 117.6(3) . . ? N12 N11 Fe1 117.66(13) . . ? C11 N11 Fe1 137.68(15) . . ? C11 N11 N12 104.18(17) . . ? N11 N12 C1 119.94(18) . . ? C13 N12 N11 112.40(17) . . ? C13 N12 C1 127.5(2) . . ? N42 N41 Fe1 116.87(13) . . ? C41 N41 Fe1 138.69(15) . . ? C41 N41 N42 104.43(17) . . ? N41 N42 C7 120.07(19) . . ? C43 N42 N41 111.65(19) . . ? C43 N42 C7 127.2(2) . . ? N12 C1 N12 111.6(2) 7_565 . ? N12 C1 H1 107.6(9) . . ? N12 C1 H1 107.6(9) 7_565 . ? N12 C1 C2 111.86(16) . . ? N12 C1 C2 111.86(16) 7_565 . ? C2 C1 H1 106.1(17) . . ? N1 C2 C1 117.7(3) . . ? N1 C2 C3 123.0(3) . . ? C3 C2 C1 119.3(3) . . ? C2 C3 H3 118.2(18) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3 122.9(18) . . ? C3 C4 H4 120(2) . . ? C3 C4 C5 118.7(3) . . ? C5 C4 H4 121(2) . . ? C4 C5 H5 120.4(18) . . ? C4 C5 C6 119.1(3) . . ? C6 C5 H5 120.4(18) . . ? N1 C6 C5 122.6(3) . . ? N1 C6 C7 117.7(3) . . ? C5 C6 C7 119.7(3) . . ? N42 C7 N42 111.0(2) . 7_565 ? N42 C7 C6 112.42(16) 7_565 . ? N42 C7 C6 112.42(16) . . ? N42 C7 H7 105.6(10) 7_565 . ? N42 C7 H7 105.6(10) . . ? C6 C7 H7 109.3(19) . . ? H10a C10 H10b 104(2) . . ? H10a C10 H10c 107(2) . . ? H10b C10 H10c 108(2) . . ? C11 C10 H10a 114(2) . . ? C11 C10 H10b 113.2(16) . . ? C11 C10 H10c 110.4(16) . . ? N11 C11 C10 123.1(2) . . ? N11 C11 C12 110.46(19) . . ? C12 C11 C10 126.4(2) . . ? C11 C12 H12 126.5(14) . . ? C13 C12 C11 107.2(2) . . ? C13 C12 H12 126.2(14) . . ? N12 C13 C12 105.70(19) . . ? N12 C13 C14 124.4(2) . . ? C12 C13 C14 129.8(2) . . ? C13 C14 H14a 107.4(15) . . ? C13 C14 H14b 112.8(17) . . ? C13 C14 H14c 109(2) . . ? H14a C14 H14b 110(2) . . ? H14a C14 H14c 112(3) . . ? H14b C14 H14c 105(3) . . ? H40a C40 H40b 107(2) . . ? H40a C40 H40c 108(2) . . ? H40b C40 H40c 112(2) . . ? C41 C40 H40a 112.0(14) . . ? C41 C40 H40b 109.4(17) . . ? C41 C40 H40c 109.3(16) . . ? N41 C41 C40 123.2(2) . . ? N41 C41 C42 110.5(2) . . ? C42 C41 C40 126.2(2) . . ? C41 C42 H42 125.9(15) . . ? C43 C42 C41 107.4(2) . . ? C43 C42 H42 126.8(15) . . ? N42 C43 C44 123.7(2) . . ? C42 C43 N42 106.0(2) . . ? C42 C43 C44 130.3(2) . . ? C43 C44 H44a 115(2) . . ? C43 C44 H44b 109(2) . . ? C43 C44 H44c 110(2) . . ? H44a C44 H44b 112(3) . . ? H44a C44 H44c 105(3) . . ? H44b C44 H44c 105(3) . . ? C1S O1S H1S 100(3) . . ? O1S C1S H1Sa 109.5 . . ? O1S C1S H1Sb 109.5 . . ? O1S C1S H1Sc 109.5 . . ? H1Sa C1S H1Sb 109.5 . . ? H1Sa C1S H1Sc 109.5 . . ? H1Sb C1S H1Sc 109.5 . . ? 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 Fe1 N1 C2 C1 0.0 . . . . ? Fe1 N1 C2 C3 180.0 . . . . ? Fe1 N1 C6 C5 180.0 . . . . ? Fe1 N1 C6 C7 0.0 . . . . ? Fe1 N11 C11 C10 -7.0(3) . . . . ? Fe1 N11 C11 C12 171.89(16) . . . . ? Fe1 N41 C41 C40 -1.6(3) . . . . ? Fe1 N41 C41 C42 179.91(17) . . . . ? Cl1 Fe1 N1 C2 0.000(2) . . . . ? Cl1 Fe1 N1 C6 180.000(2) . . . . ? Cl1 Fe1 N11 N12 134.39(13) . . . . ? Cl1 Fe1 N11 C11 -36.1(2) . . . . ? Cl1 Fe1 N41 N42 -149.72(13) . . . . ? Cl1 Fe1 N41 C41 29.5(2) . . . . ? N1 Fe1 N11 N12 -43.47(14) . . . . ? N1 Fe1 N11 C11 146.1(2) . . . . ? N1 Fe1 N41 N42 32.25(14) . . . . ? N1 Fe1 N41 C41 -148.5(2) . . . . ? N1 C2 C1 N12 -62.99(18) . . . . ? N1 C2 C1 N12 62.99(18) . . . 7_565 ? N1 C6 C5 C4 0.0 . . . . ? N1 C6 C7 N42 63.04(18) . . . . ? N1 C6 C7 N42 -63.04(18) . . . 7_565 ? N11 Fe1 N1 C2 41.94(5) . . . . ? N11 Fe1 N1 C2 -41.94(5) 7_565 . . . ? N11 Fe1 N1 C6 -138.06(5) . . . . ? N11 Fe1 N1 C6 138.06(5) 7_565 . . . ? N11 Fe1 N11 N12 39.12(16) 7_565 . . . ? N11 Fe1 N11 C11 -131.33(19) 7_565 . . . ? N11 Fe1 N41 N42 16.4(3) 7_565 . . . ? N11 Fe1 N41 N42 112.72(14) . . . . ? N11 Fe1 N41 C41 -68.1(2) . . . . ? N11 Fe1 N41 C41 -164.4(2) 7_565 . . . ? N11 N12 C1 N12 -65.2(3) . . . 7_565 ? N11 N12 C1 C2 60.9(3) . . . . ? N11 N12 C13 C12 -1.0(2) . . . . ? N11 N12 C13 C14 176.0(2) . . . . ? N12 N11 C11 C10 -178.3(2) . . . . ? N12 N11 C11 C12 0.6(2) . . . . ? N12 C13 C12 C11 1.3(2) . . . . ? N41 Fe1 N1 C2 -142.23(5) 7_565 . . . ? N41 Fe1 N1 C2 142.23(5) . . . . ? N41 Fe1 N1 C6 -37.77(5) . . . . ? N41 Fe1 N1 C6 37.77(5) 7_565 . . . ? N41 Fe1 N11 N12 -125.54(14) . . . . ? N41 Fe1 N11 N12 -59.4(3) 7_565 . . . ? N41 Fe1 N11 C11 64.0(2) . . . . ? N41 Fe1 N11 C11 130.2(3) 7_565 . . . ? N41 Fe1 N41 N42 -52.80(16) 7_565 . . . ? N41 Fe1 N41 C41 126.4(2) 7_565 . . . ? N41 N42 C7 N42 58.0(3) . . . 7_565 ? N41 N42 C7 C6 -68.9(3) . . . . ? N41 N42 C43 C42 0.5(3) . . . . ? N41 N42 C43 C44 -178.7(3) . . . . ? N42 N41 C41 C40 177.7(2) . . . . ? N42 N41 C41 C42 -0.8(2) . . . . ? N42 C43 C42 C41 -0.9(3) . . . . ? C1 N12 N11 Fe1 2.5(2) . . . . ? C1 N12 N11 C11 175.92(19) . . . . ? C1 N12 C13 C12 -176.3(2) . . . . ? C1 N12 C13 C14 0.7(4) . . . . ? C2 N1 C6 C5 0.0 . . . . ? C2 N1 C6 C7 180.0 . . . . ? C3 C2 C1 N12 117.01(18) . . . . ? C3 C2 C1 N12 -117.01(18) . . . 7_565 ? C4 C3 C2 N1 0.0 . . . . ? C4 C3 C2 C1 180.0 . . . . ? C5 C4 C3 C2 0.0 . . . . ? C5 C6 C7 N42 -116.96(18) . . . . ? C5 C6 C7 N42 116.96(18) . . . 7_565 ? C6 N1 C2 C1 180.0 . . . . ? C6 N1 C2 C3 0.0 . . . . ? C6 C5 C4 C3 0.0 . . . . ? C7 N42 N41 Fe1 10.7(2) . . . . ? C7 N42 N41 C41 -168.8(2) . . . . ? C7 N42 C43 C42 168.5(2) . . . . ? C7 N42 C43 C44 -10.6(4) . . . . ? C7 C6 C5 C4 180.0 . . . . ? C13 N12 N11 Fe1 -173.14(13) . . . . ? C13 N12 N11 C11 0.2(2) . . . . ? C13 N12 C1 N12 109.7(2) . . . 7_565 ? C13 N12 C1 C2 -124.1(2) . . . . ? C13 C12 C11 N11 -1.2(3) . . . . ? C13 C12 C11 C10 177.6(2) . . . . ? C14 C13 C12 C11 -175.4(2) . . . . ? C43 N42 N41 Fe1 179.69(15) . . . . ? C43 N42 N41 C41 0.2(2) . . . . ? C43 N42 C7 N42 -109.2(3) . . . 7_565 ? C43 N42 C7 C6 124.0(3) . . . . ? C43 C42 C41 N41 1.1(3) . . . . ? C43 C42 C41 C40 -177.3(2) . . . . ? C44 C43 C42 C41 178.1(3) . . . . ? #===END data_3xMeOH_gard5ba _database_code_depnum_ccdc_archive 'CCDC 821761' #TrackingRef '- FeClpzR4lutCl_06022011.cif' _audit_creation_date 2011-05-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.108(Br), C27 H33 Cl Fe N9, 0.892(Cl1), C H4 O' _chemical_formula_sum 'C28 H37 Br0.11 Cl1.89 Fe N9 O' _chemical_formula_weight 647.31 _chemical_melting_point ? 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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.7842(2) _cell_length_b 12.5916(4) _cell_length_c 13.7985(4) _cell_angle_alpha 78.599(2) _cell_angle_beta 84.392(2) _cell_angle_gamma 88.6900(10) _cell_volume 1488.93(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2677 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 65 _cell_measurement_theta_min 3 _exptl_absorpt_coefficient_mu 6.111 _exptl_absorpt_correction_T_max 0.8379 _exptl_absorpt_correction_T_min 0.3745 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Numerical (based on real shape of the crystal) absorption correction followed by: SADABS. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 676 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_unetI/netI 0.0526 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 12381 _diffrn_reflns_theta_full 67.00 _diffrn_reflns_theta_max 67.10 _diffrn_reflns_theta_min 3.28 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.919 _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3855 _reflns_number_total 4889 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_collection 'APEX2 v2.0-2 (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _refine_diff_density_max 0.323 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.065 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 395 _refine_ls_number_reflns 4889 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0562 _refine_ls_R_factor_gt 0.0410 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0886 _refine_ls_wR_factor_ref 0.0930 _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. The hydrogen atoms were put in geometrically calculated positions with Uiso = 1.2 Uiso/eq of an adjacent atom (1.5 Uiso/eq for methyl groups) and refined within a riding model using appropriate fixed distances to the adjacent atoms. The methyl hydrogens' positions were optimized rotationally to fit the residual electron density. Hydrogen atoms of solvent molecules were found objectively and refined in isotropic approximation unrestrained The refinement of atom Cl2 resulted in negative thermal coefficients; therefore it was refined as a mixture of Cl and Br atoms with coordinates and thermal parameters of both that were restricted to be equal and with a total occupancy set to be unity. The ratio Cl/Br was refined to a 81/11 value ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Br2 Br 0.28088(8) 0.18357(5) 0.28250(5) 0.0230(3) Uani 0.108(3) 1 d P A 2 Fe1 Fe -0.59571(5) 0.70049(4) 0.21729(3) 0.01329(14) Uani 1 1 d . . . Cl1 Cl -0.83576(8) 0.68132(6) 0.30947(5) 0.01813(17) Uani 1 1 d . . . N1 N -0.3698(3) 0.71943(18) 0.13004(16) 0.0118(5) Uani 1 1 d . . . N11 N -0.4820(3) 0.78672(18) 0.31903(17) 0.0146(5) Uani 1 1 d . . . N12 N -0.3312(3) 0.76059(19) 0.33365(17) 0.0150(5) Uani 1 1 d . . . N21 N -0.4830(3) 0.56299(19) 0.31660(17) 0.0138(5) Uani 1 1 d . . . N22 N -0.3280(3) 0.57183(19) 0.32312(17) 0.0145(5) Uani 1 1 d . . . N31 N -0.6528(3) 0.61547(19) 0.09465(17) 0.0160(5) Uani 1 1 d . . . N32 N -0.5943(3) 0.65940(19) -0.00128(17) 0.0158(5) Uani 1 1 d . . . N41 N -0.6631(3) 0.84382(19) 0.09906(17) 0.0165(6) Uani 1 1 d . . . N42 N -0.5972(3) 0.84800(19) 0.00296(17) 0.0167(6) Uani 1 1 d . . . C1 C -0.2541(3) 0.6768(2) 0.2873(2) 0.0139(6) Uani 1 1 d . . . H1 H -0.1480 0.6697 0.3085 0.017 Uiso 1 1 calc R . . C2 C -0.2391(3) 0.7066(2) 0.1746(2) 0.0138(6) Uani 1 1 d . . . C3 C -0.0963(3) 0.7180(2) 0.1227(2) 0.0158(7) Uani 1 1 d . . . H3 H -0.0070 0.7096 0.1571 0.019 Uiso 1 1 calc R . . C4 C -0.0842(4) 0.7419(2) 0.0196(2) 0.0192(7) Uani 1 1 d . . . H4 H 0.0130 0.7489 -0.0179 0.023 Uiso 1 1 calc R . . C5 C -0.2186(3) 0.7551(2) -0.0273(2) 0.0148(6) Uani 1 1 d . . . H5 H -0.2147 0.7719 -0.0977 0.018 Uiso 1 1 calc R . . C6 C -0.3579(3) 0.7437(2) 0.0298(2) 0.0151(6) Uani 1 1 d . . . C7 C -0.5040(3) 0.7579(2) -0.0208(2) 0.0147(6) Uani 1 1 d . . . H7 H -0.4736 0.7752 -0.0939 0.018 Uiso 1 1 calc R . . C10 C -0.6814(3) 0.8970(3) 0.3951(2) 0.0207(7) Uani 1 1 d . . . H10a H -0.6829 0.9688 0.3520 0.031 Uiso 1 1 calc R . . H10b H -0.7081 0.9037 0.4642 0.031 Uiso 1 1 calc R . . H10c H -0.7557 0.8500 0.3757 0.031 Uiso 1 1 calc R . . C11 C -0.5254(3) 0.8489(2) 0.3849(2) 0.0157(7) Uani 1 1 d . . . C12 C -0.4053(3) 0.8613(2) 0.4416(2) 0.0176(7) Uani 1 1 d . . . H12 H -0.4082 0.9015 0.4932 0.021 Uiso 1 1 calc R . . C13 C -0.2837(3) 0.8046(2) 0.4085(2) 0.0172(7) Uani 1 1 d . . . C14 C -0.1269(3) 0.7934(3) 0.4429(2) 0.0218(7) Uani 1 1 d . . . H14a H -0.0937 0.7177 0.4502 0.033 Uiso 1 1 calc R . . H14b H -0.1286 0.8160 0.5070 0.033 Uiso 1 1 calc R . . H14c H -0.0557 0.8393 0.3940 0.033 Uiso 1 1 calc R . . C20 C -0.6816(3) 0.4251(2) 0.3931(2) 0.0170(7) Uani 1 1 d . . . H20a H -0.7526 0.4828 0.3677 0.026 Uiso 1 1 calc R . . H20b H -0.7082 0.3996 0.4644 0.026 Uiso 1 1 calc R . . H20c H -0.6886 0.3649 0.3584 0.026 Uiso 1 1 calc R . . C21 C -0.5228(3) 0.4678(2) 0.3759(2) 0.0159(7) Uani 1 1 d . . . C22 C -0.3957(3) 0.4166(2) 0.4182(2) 0.0166(7) Uani 1 1 d . . . H22 H -0.3945 0.3481 0.4619 0.020 Uiso 1 1 calc R . . C23 C -0.2738(3) 0.4830(2) 0.3853(2) 0.0158(7) Uani 1 1 d . . . C24 C -0.1102(3) 0.4641(2) 0.4044(2) 0.0205(7) Uani 1 1 d . . . H24a H -0.1043 0.4171 0.4696 0.031 Uiso 1 1 calc R . . H24b H -0.0611 0.5335 0.4031 0.031 Uiso 1 1 calc R . . H24c H -0.0577 0.4291 0.3529 0.031 Uiso 1 1 calc R . . C30 C -0.8394(4) 0.4686(2) 0.1695(2) 0.0229(7) Uani 1 1 d . . . H30a H -0.7792 0.4043 0.1947 0.034 Uiso 1 1 calc R . . H30b H -0.9341 0.4461 0.1474 0.034 Uiso 1 1 calc R . . H30c H -0.8642 0.5096 0.2224 0.034 Uiso 1 1 calc R . . C31 C -0.7486(3) 0.5381(2) 0.0841(2) 0.0163(7) Uani 1 1 d . . . C32 C -0.7501(3) 0.5328(2) -0.0159(2) 0.0176(7) Uani 1 1 d . . . H32 H -0.8075 0.4838 -0.0421 0.021 Uiso 1 1 calc R . . C33 C -0.6533(3) 0.6114(2) -0.0691(2) 0.0187(7) Uani 1 1 d . . . C34 C -0.6162(4) 0.6430(3) -0.1787(2) 0.0249(8) Uani 1 1 d . . . H34a H -0.6821 0.7035 -0.2053 0.037 Uiso 1 1 calc R . . H34b H -0.6333 0.5811 -0.2096 0.037 Uiso 1 1 calc R . . H34c H -0.5088 0.6651 -0.1932 0.037 Uiso 1 1 calc R . . C40 C -0.8640(4) 0.9525(2) 0.1766(2) 0.0223(7) Uani 1 1 d . . . H40a H -0.8858 0.8864 0.2267 0.033 Uiso 1 1 calc R . . H40b H -0.9602 0.9846 0.1541 0.033 Uiso 1 1 calc R . . H40c H -0.8106 1.0044 0.2056 0.033 Uiso 1 1 calc R . . C41 C -0.7653(4) 0.9251(2) 0.0901(2) 0.0191(7) Uani 1 1 d . . . C42 C -0.7648(4) 0.9786(2) -0.0083(2) 0.0195(7) Uani 1 1 d . . . H42 H -0.8271 1.0387 -0.0328 0.023 Uiso 1 1 calc R . . C43 C -0.6580(4) 0.9286(2) -0.0634(2) 0.0187(7) Uani 1 1 d . . . C44 C -0.6105(4) 0.9519(3) -0.1717(2) 0.0283(8) Uani 1 1 d . . . H44a H -0.5069 0.9239 -0.1839 0.042 Uiso 0.50 1 calc PR . . H44b H -0.6119 1.0304 -0.1967 0.042 Uiso 0.50 1 calc PR . . H44c H -0.6815 0.9169 -0.2061 0.042 Uiso 0.50 1 calc PR . . H44d H -0.6933 0.9902 -0.2072 0.042 Uiso 0.50 1 calc PR . . H44e H -0.5883 0.8837 -0.1944 0.042 Uiso 0.50 1 calc PR . . H44f H -0.5187 0.9972 -0.1851 0.042 Uiso 0.50 1 calc PR . . Cl2 Cl 0.28088(8) 0.18357(5) 0.28250(5) 0.0230(3) Uani 0.892(3) 1 d P A 1 O1S O -0.0664(4) 0.2032(3) 0.2487(2) 0.0680(10) Uani 1 1 d . . . H1S H 0.033(7) 0.208(5) 0.272(5) 0.14(3) Uiso 1 1 d . . . C1S C -0.1343(6) 0.1551(5) 0.3427(4) 0.0590(14) Uani 1 1 d . . . H1Sa H -0.241(6) 0.158(4) 0.344(3) 0.068(15) Uiso 1 1 d . . . H1Sb H -0.102(7) 0.184(5) 0.399(4) 0.12(2) Uiso 1 1 d . . . H1Sc H -0.096(6) 0.079(5) 0.351(4) 0.10(2) Uiso 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 Br2 0.0314(4) 0.0183(4) 0.0198(4) -0.0044(3) -0.0024(3) -0.0021(3) Fe1 0.0113(3) 0.0153(3) 0.0135(3) -0.00308(19) -0.00186(18) -0.00107(19) Cl1 0.0129(4) 0.0199(4) 0.0212(4) -0.0035(3) -0.0004(3) -0.0012(3) N1 0.0135(13) 0.0107(12) 0.0114(13) -0.0023(10) -0.0013(10) -0.0006(10) N11 0.0150(14) 0.0115(12) 0.0173(13) -0.0025(10) -0.0029(10) -0.0007(10) N12 0.0130(13) 0.0180(13) 0.0149(13) -0.0048(10) -0.0030(10) -0.0009(10) N21 0.0101(13) 0.0153(13) 0.0172(13) -0.0056(10) -0.0019(10) 0.0002(10) N22 0.0138(13) 0.0155(13) 0.0141(13) -0.0020(10) -0.0030(10) -0.0018(10) N31 0.0218(15) 0.0149(13) 0.0108(13) -0.0001(10) -0.0038(10) -0.0029(11) N32 0.0190(14) 0.0140(13) 0.0148(13) -0.0026(10) -0.0042(10) -0.0017(11) N41 0.0194(14) 0.0161(13) 0.0145(13) -0.0030(10) -0.0040(10) 0.0020(11) N42 0.0188(14) 0.0176(13) 0.0140(13) -0.0037(11) -0.0028(10) 0.0015(11) C1 0.0114(16) 0.0157(15) 0.0145(15) -0.0020(12) -0.0022(12) -0.0031(12) C2 0.0175(17) 0.0077(14) 0.0171(16) -0.0040(12) -0.0032(13) 0.0000(12) C3 0.0152(17) 0.0143(15) 0.0189(17) -0.0044(13) -0.0041(13) -0.0024(12) C4 0.0190(18) 0.0170(16) 0.0208(17) -0.0048(13) 0.0041(13) -0.0026(13) C5 0.0205(17) 0.0113(15) 0.0133(16) -0.0049(12) 0.0004(12) -0.0014(12) C6 0.0190(17) 0.0102(15) 0.0170(16) -0.0039(12) -0.0034(13) -0.0011(12) C7 0.0179(16) 0.0127(15) 0.0130(15) -0.0013(12) -0.0013(12) -0.0017(12) C10 0.0208(18) 0.0244(17) 0.0177(17) -0.0057(14) -0.0032(13) 0.0030(14) C11 0.0210(17) 0.0153(15) 0.0099(15) -0.0004(12) 0.0003(12) -0.0038(13) C12 0.0205(17) 0.0185(16) 0.0143(16) -0.0037(13) -0.0028(13) -0.0008(13) C13 0.0158(17) 0.0193(16) 0.0167(16) -0.0027(13) -0.0017(12) -0.0070(13) C14 0.0173(18) 0.0284(18) 0.0232(18) -0.0112(14) -0.0060(13) -0.0014(14) C20 0.0172(17) 0.0176(16) 0.0164(16) -0.0038(13) -0.0007(12) -0.0024(13) C21 0.0177(17) 0.0145(15) 0.0162(16) -0.0048(12) 0.0000(12) -0.0047(13) C22 0.0215(18) 0.0168(16) 0.0106(15) 0.0000(12) -0.0033(12) 0.0005(13) C23 0.0179(17) 0.0212(16) 0.0088(15) -0.0041(12) -0.0022(12) 0.0019(13) C24 0.0160(17) 0.0210(17) 0.0225(18) 0.0019(14) -0.0049(13) -0.0003(13) C30 0.0267(19) 0.0198(17) 0.0218(18) -0.0024(14) -0.0025(14) -0.0066(14) C31 0.0187(17) 0.0123(15) 0.0176(16) -0.0021(12) -0.0029(13) 0.0030(13) C32 0.0201(17) 0.0171(16) 0.0180(16) -0.0066(13) -0.0063(13) -0.0026(13) C33 0.0184(17) 0.0205(17) 0.0196(17) -0.0078(13) -0.0070(13) 0.0036(13) C34 0.031(2) 0.0262(18) 0.0194(18) -0.0091(14) -0.0022(14) -0.0066(15) C40 0.0268(19) 0.0202(17) 0.0205(17) -0.0053(14) -0.0054(14) 0.0090(14) C41 0.0200(17) 0.0182(16) 0.0210(17) -0.0062(13) -0.0058(13) -0.0009(13) C42 0.0242(18) 0.0150(16) 0.0205(17) -0.0028(13) -0.0098(14) 0.0029(13) C43 0.0220(18) 0.0166(16) 0.0181(17) -0.0020(13) -0.0066(13) -0.0035(13) C44 0.043(2) 0.0239(18) 0.0145(17) 0.0035(14) -0.0030(15) 0.0075(16) Cl2 0.0314(4) 0.0183(4) 0.0198(4) -0.0044(3) -0.0024(3) -0.0021(3) O1S 0.041(2) 0.115(3) 0.0353(18) 0.0148(17) -0.0003(15) 0.0068(19) C1S 0.041(3) 0.087(4) 0.045(3) 0.002(3) -0.013(2) -0.008(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 Cl1 2.3452(8) . ? Fe1 N1 2.210(2) . ? Fe1 N11 2.252(2) . ? Fe1 N21 2.259(2) . ? Fe1 N31 2.273(2) . ? Fe1 N41 2.290(2) . ? N1 C2 1.346(4) . ? N1 C6 1.350(4) . ? N11 C11 1.335(4) . ? N12 N11 1.382(3) . ? N12 C1 1.459(4) . ? N12 C13 1.368(4) . ? N21 C21 1.343(4) . ? N22 N21 1.381(3) . ? N22 C1 1.460(4) . ? N22 C23 1.375(4) . ? N31 C31 1.340(4) . ? N32 N31 1.383(3) . ? N32 C7 1.453(4) . ? N32 C33 1.357(4) . ? N41 C41 1.341(4) . ? N42 N41 1.386(3) . ? N42 C7 1.455(4) . ? N42 C43 1.363(4) . ? C1 H1 1.0000 . ? C2 C1 1.520(4) . ? C3 C2 1.378(4) . ? C3 H3 0.9500 . ? C4 C3 1.389(4) . ? C4 H4 0.9500 . ? C5 C4 1.392(4) . ? C5 H5 0.9500 . ? C6 C5 1.383(4) . ? C6 C7 1.511(4) . ? C7 H7 1.0000 . ? C10 H10a 0.9800 . ? C10 H10b 0.9800 . ? C10 H10c 0.9800 . ? C11 C10 1.491(4) . ? C12 C11 1.403(4) . ? C12 H12 0.9500 . ? C13 C12 1.362(4) . ? C13 C14 1.494(4) . ? C14 H14a 0.9800 . ? C14 H14b 0.9800 . ? C14 H14c 0.9800 . ? C20 H20a 0.9800 . ? C20 H20b 0.9800 . ? C20 H20c 0.9800 . ? C21 C20 1.486(4) . ? C22 C21 1.396(4) . ? C22 H22 0.9500 . ? C23 C22 1.359(4) . ? C23 C24 1.492(4) . ? C24 H24a 0.9800 . ? C24 H24b 0.9800 . ? C24 H24c 0.9800 . ? C30 H30a 0.9800 . ? C30 H30b 0.9800 . ? C30 H30c 0.9800 . ? C31 C30 1.494(4) . ? C32 C31 1.396(4) . ? C32 H32 0.9500 . ? C33 C32 1.368(4) . ? C33 C34 1.491(4) . ? C34 H34a 0.9800 . ? C34 H34b 0.9800 . ? C34 H34c 0.9800 . ? C40 H40a 0.9800 . ? C40 H40b 0.9800 . ? C40 H40c 0.9800 . ? C41 C40 1.497(4) . ? C42 C41 1.391(4) . ? C42 H42 0.9500 . ? C43 C42 1.370(4) . ? C43 C44 1.486(4) . ? C44 H44a 0.9800 . ? C44 H44b 0.9800 . ? C44 H44c 0.9800 . ? C44 H44d 0.9800 . ? C44 H44e 0.9800 . ? C44 H44f 0.9800 . ? O1S H1S 0.96(6) . ? O1S C1S 1.400(6) . ? C1S H1Sa 0.93(5) . ? C1S H1Sb 1.00(6) . ? C1S H1Sc 1.00(6) . ? 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 N1 Fe1 Cl1 179.70(7) . . ? N1 Fe1 N11 83.45(9) . . ? N1 Fe1 N21 84.77(8) . . ? N1 Fe1 N31 82.67(9) . . ? N1 Fe1 N41 83.82(9) . . ? N11 Fe1 Cl1 96.52(6) . . ? N11 Fe1 N21 77.50(8) . . ? N11 Fe1 N31 166.08(9) . . ? N11 Fe1 N41 101.01(9) . . ? N21 Fe1 Cl1 95.51(6) . . ? N21 Fe1 N31 100.19(9) . . ? N21 Fe1 N41 168.59(9) . . ? N31 Fe1 Cl1 97.38(7) . . ? N31 Fe1 N41 78.49(9) . . ? N41 Fe1 Cl1 95.90(7) . . ? C2 N1 Fe1 121.40(18) . . ? C2 N1 C6 117.5(2) . . ? C6 N1 Fe1 121.10(19) . . ? N12 N11 Fe1 117.30(17) . . ? C11 N11 Fe1 137.1(2) . . ? C11 N11 N12 104.8(2) . . ? N11 N12 C1 120.0(2) . . ? C13 N12 N11 111.4(2) . . ? C13 N12 C1 127.2(2) . . ? N22 N21 Fe1 117.01(17) . . ? C21 N21 Fe1 138.3(2) . . ? C21 N21 N22 104.7(2) . . ? N21 N22 C1 119.1(2) . . ? C23 N22 N21 111.1(2) . . ? C23 N22 C1 127.8(2) . . ? N32 N31 Fe1 117.39(17) . . ? C31 N31 Fe1 137.50(19) . . ? C31 N31 N32 104.4(2) . . ? N31 N32 C7 120.0(2) . . ? C33 N32 N31 111.9(2) . . ? C33 N32 C7 127.1(2) . . ? N42 N41 Fe1 116.84(17) . . ? C41 N41 Fe1 138.6(2) . . ? C41 N41 N42 104.0(2) . . ? N41 N42 C7 119.9(2) . . ? C43 N42 N41 112.2(2) . . ? C43 N42 C7 126.3(2) . . ? N12 C1 N22 111.2(2) . . ? N12 C1 H1 107.0 . . ? N12 C1 C2 112.7(2) . . ? N22 C1 H1 107.0 . . ? N22 C1 C2 111.4(2) . . ? C2 C1 H1 107.0 . . ? N1 C2 C1 117.0(2) . . ? N1 C2 C3 123.0(3) . . ? C3 C2 C1 120.0(3) . . ? C2 C3 H3 120.3 . . ? C2 C3 C4 119.4(3) . . ? C4 C3 H3 120.3 . . ? C3 C4 H4 121.0 . . ? C3 C4 C5 118.0(3) . . ? C5 C4 H4 121.0 . . ? C4 C5 H5 120.4 . . ? C6 C5 C4 119.3(3) . . ? C6 C5 H5 120.4 . . ? N1 C6 C5 122.7(3) . . ? N1 C6 C7 117.8(3) . . ? C5 C6 C7 119.4(3) . . ? N32 C7 N42 110.3(2) . . ? N32 C7 C6 112.6(2) . . ? N32 C7 H7 106.9 . . ? N42 C7 C6 113.0(2) . . ? N42 C7 H7 106.9 . . ? C6 C7 H7 106.9 . . ? H10a C10 H10b 109.5 . . ? H10a C10 H10c 109.5 . . ? H10b C10 H10c 109.5 . . ? C11 C10 H10a 109.5 . . ? C11 C10 H10b 109.5 . . ? C11 C10 H10c 109.5 . . ? N11 C11 C10 123.5(3) . . ? N11 C11 C12 110.7(3) . . ? C12 C11 C10 125.8(3) . . ? C11 C12 H12 126.6 . . ? C13 C12 C11 106.9(3) . . ? C13 C12 H12 126.6 . . ? N12 C13 C14 125.4(3) . . ? C12 C13 N12 106.2(3) . . ? C12 C13 C14 128.3(3) . . ? C13 C14 H14a 109.5 . . ? C13 C14 H14b 109.5 . . ? C13 C14 H14c 109.5 . . ? H14a C14 H14b 109.5 . . ? H14a C14 H14c 109.5 . . ? H14b C14 H14c 109.5 . . ? H20a C20 H20b 109.5 . . ? H20a C20 H20c 109.5 . . ? H20b C20 H20c 109.5 . . ? C21 C20 H20a 109.5 . . ? C21 C20 H20b 109.5 . . ? C21 C20 H20c 109.5 . . ? N21 C21 C20 123.6(3) . . ? N21 C21 C22 110.6(3) . . ? C22 C21 C20 125.8(3) . . ? C21 C22 H22 126.4 . . ? C23 C22 C21 107.3(3) . . ? C23 C22 H22 126.4 . . ? N22 C23 C24 124.8(3) . . ? C22 C23 N22 106.2(3) . . ? C22 C23 C24 128.8(3) . . ? C23 C24 H24a 109.5 . . ? C23 C24 H24b 109.5 . . ? C23 C24 H24c 109.5 . . ? H24a C24 H24b 109.5 . . ? H24a C24 H24c 109.5 . . ? H24b C24 H24c 109.5 . . ? H30a C30 H30b 109.5 . . ? H30a C30 H30c 109.5 . . ? H30b C30 H30c 109.5 . . ? C31 C30 H30a 109.5 . . ? C31 C30 H30b 109.5 . . ? C31 C30 H30c 109.5 . . ? N31 C31 C30 123.3(3) . . ? N31 C31 C32 110.7(3) . . ? C32 C31 C30 126.0(3) . . ? C31 C32 H32 126.5 . . ? C33 C32 C31 107.0(3) . . ? C33 C32 H32 126.5 . . ? N32 C33 C32 106.0(3) . . ? N32 C33 C34 124.6(3) . . ? C32 C33 C34 129.3(3) . . ? C33 C34 H34a 109.5 . . ? C33 C34 H34b 109.5 . . ? C33 C34 H34c 109.5 . . ? H34a C34 H34b 109.5 . . ? H34a C34 H34c 109.5 . . ? H34b C34 H34c 109.5 . . ? H40a C40 H40b 109.5 . . ? H40a C40 H40c 109.5 . . ? H40b C40 H40c 109.5 . . ? C41 C40 H40a 109.5 . . ? C41 C40 H40b 109.5 . . ? C41 C40 H40c 109.5 . . ? N41 C41 C40 123.1(3) . . ? N41 C41 C42 110.9(3) . . ? C42 C41 C40 126.0(3) . . ? C41 C42 H42 126.3 . . ? C43 C42 C41 107.4(3) . . ? C43 C42 H42 126.3 . . ? N42 C43 C42 105.5(3) . . ? N42 C43 C44 124.2(3) . . ? C42 C43 C44 130.3(3) . . ? C43 C44 H44a 109.5 . . ? C43 C44 H44b 109.5 . . ? C43 C44 H44c 109.5 . . ? C43 C44 H44d 109.5 . . ? C43 C44 H44e 109.5 . . ? C43 C44 H44f 109.5 . . ? H44a C44 H44b 109.5 . . ? H44a C44 H44c 109.5 . . ? H44a C44 H44d 141.1 . . ? H44a C44 H44e 56.3 . . ? H44a C44 H44f 56.3 . . ? H44b C44 H44c 109.5 . . ? H44b C44 H44d 56.3 . . ? H44b C44 H44e 141.1 . . ? H44b C44 H44f 56.3 . . ? H44c C44 H44d 56.3 . . ? H44c C44 H44e 56.3 . . ? H44c C44 H44f 141.1 . . ? H44d C44 H44e 109.5 . . ? H44d C44 H44f 109.5 . . ? H44e C44 H44f 109.5 . . ? C1S O1S H1S 93(4) . . ? O1S C1S H1Sa 111(3) . . ? O1S C1S H1Sb 116(4) . . ? O1S C1S H1Sc 103(3) . . ? H1Sa C1S H1Sb 109(4) . . ? H1Sa C1S H1Sc 112(4) . . ? H1Sb C1S H1Sc 106(4) . . ? 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 O1S H1S Br2 0.96(6) 2.21(6) 3.128(3) 159(6) . O1S H1S Cl2 0.96(6) 2.21(6) 3.128(3) 159(6) . 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 Fe1 N1 C2 C1 0.9(3) . . . . ? Fe1 N1 C2 C3 -179.9(2) . . . . ? Fe1 N1 C6 C5 -179.4(2) . . . . ? Fe1 N1 C6 C7 0.2(3) . . . . ? Fe1 N11 C11 C10 -12.2(5) . . . . ? Fe1 N11 C11 C12 167.6(2) . . . . ? Fe1 N21 C21 C20 -1.0(5) . . . . ? Fe1 N21 C21 C22 179.2(2) . . . . ? Fe1 N31 C31 C30 -10.6(5) . . . . ? Fe1 N31 C31 C32 169.6(2) . . . . ? Fe1 N41 C41 C40 9.6(5) . . . . ? Fe1 N41 C41 C42 -170.8(2) . . . . ? Cl1 Fe1 N1 C2 122(14) . . . . ? Cl1 Fe1 N1 C6 -58(14) . . . . ? Cl1 Fe1 N11 N12 141.82(17) . . . . ? Cl1 Fe1 N11 C11 -25.5(3) . . . . ? Cl1 Fe1 N21 N22 -149.68(17) . . . . ? Cl1 Fe1 N21 C21 30.4(3) . . . . ? Cl1 Fe1 N31 N32 140.36(18) . . . . ? Cl1 Fe1 N31 C31 -27.9(3) . . . . ? Cl1 Fe1 N41 N42 -144.68(18) . . . . ? Cl1 Fe1 N41 C41 25.6(3) . . . . ? N1 Fe1 N11 N12 -38.48(18) . . . . ? N1 Fe1 N11 C11 154.2(3) . . . . ? N1 Fe1 N21 N22 30.22(18) . . . . ? N1 Fe1 N21 C21 -149.7(3) . . . . ? N1 Fe1 N31 N32 -39.34(19) . . . . ? N1 Fe1 N31 C31 152.4(3) . . . . ? N1 Fe1 N41 N42 35.41(19) . . . . ? N1 Fe1 N41 C41 -154.3(3) . . . . ? N1 C2 C1 N12 -63.1(3) . . . . ? N1 C2 C1 N22 62.7(3) . . . . ? N1 C6 C5 C4 -0.4(4) . . . . ? N1 C6 C7 N32 -62.9(3) . . . . ? N1 C6 C7 N42 62.9(3) . . . . ? N11 Fe1 N1 C2 39.5(2) . . . . ? N11 Fe1 N1 C6 -140.9(2) . . . . ? N11 Fe1 N21 N22 -54.21(18) . . . . ? N11 Fe1 N21 C21 125.8(3) . . . . ? N11 Fe1 N31 N32 -43.6(5) . . . . ? N11 Fe1 N31 C31 148.2(3) . . . . ? N11 Fe1 N41 N42 117.48(19) . . . . ? N11 Fe1 N41 C41 -72.2(3) . . . . ? N11 N12 C1 N22 -62.2(3) . . . . ? N11 N12 C1 C2 63.8(3) . . . . ? N11 N12 C13 C12 -0.9(3) . . . . ? N11 N12 C13 C14 -179.3(3) . . . . ? N12 N11 C11 C10 179.5(3) . . . . ? N12 N11 C11 C12 -0.8(3) . . . . ? N12 C13 C12 C11 0.4(3) . . . . ? N21 Fe1 N1 C2 -38.5(2) . . . . ? N21 Fe1 N1 C6 141.1(2) . . . . ? N21 Fe1 N11 N12 47.59(18) . . . . ? N21 Fe1 N11 C11 -119.7(3) . . . . ? N21 Fe1 N31 N32 -122.66(19) . . . . ? N21 Fe1 N31 C31 69.1(3) . . . . ? N21 Fe1 N41 N42 36.1(5) . . . . ? N21 Fe1 N41 C41 -153.6(4) . . . . ? N21 N22 C1 N12 54.2(3) . . . . ? N21 N22 C1 C2 -72.5(3) . . . . ? N21 N22 C23 C22 0.4(3) . . . . ? N21 N22 C23 C24 176.5(3) . . . . ? N22 N21 C21 C20 179.1(3) . . . . ? N22 N21 C21 C22 -0.8(3) . . . . ? N22 C23 C22 C21 -0.8(3) . . . . ? N31 Fe1 N1 C2 -139.5(2) . . . . ? N31 Fe1 N1 C6 40.1(2) . . . . ? N31 Fe1 N11 N12 -34.3(5) . . . . ? N31 Fe1 N11 C11 158.4(3) . . . . ? N31 Fe1 N21 N22 111.79(18) . . . . ? N31 Fe1 N21 C21 -68.2(3) . . . . ? N31 Fe1 N41 N42 -48.33(19) . . . . ? N31 Fe1 N41 C41 122.0(3) . . . . ? N31 N32 C7 N42 -64.2(3) . . . . ? N31 N32 C7 C6 63.0(3) . . . . ? N31 N32 C33 C32 -1.3(3) . . . . ? N31 N32 C33 C34 178.2(3) . . . . ? N32 N31 C31 C30 -179.8(3) . . . . ? N32 N31 C31 C32 0.4(3) . . . . ? N32 C33 C32 C31 1.4(3) . . . . ? N41 Fe1 N1 C2 141.4(2) . . . . ? N41 Fe1 N1 C6 -39.0(2) . . . . ? N41 Fe1 N11 N12 -120.85(18) . . . . ? N41 Fe1 N11 C11 71.8(3) . . . . ? N41 Fe1 N21 N22 29.5(5) . . . . ? N41 Fe1 N21 C21 -150.5(4) . . . . ? N41 Fe1 N31 N32 45.80(19) . . . . ? N41 Fe1 N31 C31 -122.4(3) . . . . ? N41 N42 C7 N32 60.7(3) . . . . ? N41 N42 C7 C6 -66.3(3) . . . . ? N41 N42 C43 C42 0.7(3) . . . . ? N41 N42 C43 C44 -179.6(3) . . . . ? N42 N41 C41 C40 -179.3(3) . . . . ? N42 N41 C41 C42 0.3(3) . . . . ? N42 C43 C42 C41 -0.4(3) . . . . ? C1 N12 N11 Fe1 -2.5(3) . . . . ? C1 N12 N11 C11 168.6(2) . . . . ? C1 N12 C13 C12 -167.3(3) . . . . ? C1 N12 C13 C14 14.3(5) . . . . ? C1 N22 N21 Fe1 14.8(3) . . . . ? C1 N22 N21 C21 -165.2(2) . . . . ? C1 N22 C23 C22 164.2(3) . . . . ? C1 N22 C23 C24 -19.7(4) . . . . ? C2 N1 C6 C5 0.3(4) . . . . ? C2 N1 C6 C7 179.8(2) . . . . ? C3 C2 C1 N12 117.7(3) . . . . ? C3 C2 C1 N22 -116.5(3) . . . . ? C4 C3 C2 N1 -1.2(4) . . . . ? C4 C3 C2 C1 178.0(3) . . . . ? C5 C4 C3 C2 1.0(4) . . . . ? C5 C6 C7 N32 116.7(3) . . . . ? C5 C6 C7 N42 -117.6(3) . . . . ? C6 N1 C2 C1 -178.7(2) . . . . ? C6 N1 C2 C3 0.5(4) . . . . ? C6 C5 C4 C3 -0.3(4) . . . . ? C7 N32 N31 Fe1 -1.7(3) . . . . ? C7 N32 N31 C31 170.1(2) . . . . ? C7 N32 C33 C32 -169.9(3) . . . . ? C7 N32 C33 C34 9.6(5) . . . . ? C7 N42 N41 Fe1 6.7(3) . . . . ? C7 N42 N41 C41 -166.7(3) . . . . ? C7 N42 C43 C42 165.7(3) . . . . ? C7 N42 C43 C44 -14.5(5) . . . . ? C7 C6 C5 C4 -179.9(2) . . . . ? C13 N12 N11 Fe1 -170.08(18) . . . . ? C13 N12 N11 C11 1.0(3) . . . . ? C13 N12 C1 N22 103.2(3) . . . . ? C13 N12 C1 C2 -130.8(3) . . . . ? C13 C12 C11 N11 0.3(3) . . . . ? C13 C12 C11 C10 -180.0(3) . . . . ? C14 C13 C12 C11 178.7(3) . . . . ? C23 N22 N21 Fe1 -179.75(17) . . . . ? C23 N22 N21 C21 0.2(3) . . . . ? C23 N22 C1 N12 -108.5(3) . . . . ? C23 N22 C1 C2 124.8(3) . . . . ? C23 C22 C21 N21 1.0(3) . . . . ? C23 C22 C21 C20 -178.8(3) . . . . ? C24 C23 C22 C21 -176.7(3) . . . . ? C33 N32 N31 Fe1 -171.24(19) . . . . ? C33 N32 N31 C31 0.6(3) . . . . ? C33 N32 C7 N42 103.6(3) . . . . ? C33 N32 C7 C6 -129.2(3) . . . . ? C33 C32 C31 N31 -1.1(4) . . . . ? C33 C32 C31 C30 179.0(3) . . . . ? C34 C33 C32 C31 -178.0(3) . . . . ? C43 N42 N41 Fe1 172.78(19) . . . . ? C43 N42 N41 C41 -0.6(3) . . . . ? C43 N42 C7 N32 -103.3(3) . . . . ? C43 N42 C7 C6 129.7(3) . . . . ? C43 C42 C41 N41 0.1(4) . . . . ? C43 C42 C41 C40 179.7(3) . . . . ? C44 C43 C42 C41 179.8(3) . . . . ? #===END data_4x1pt75MeOH_100K_GARD10M _database_code_depnum_ccdc_archive 'CCDC 821762' #TrackingRef '- FeClpzR4lutCl_06022011.cif' _audit_creation_date 2011-05-12 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C31 H41 Cl Fe N9, Cl, 1.75(C O)' _chemical_formula_sum 'C32.75 H41 Cl2 Fe N9 O1.75' _chemical_formula_weight 715.50 _chemical_melting_point ? 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' 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' 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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.8463(2) _cell_length_b 14.8263(3) _cell_length_c 27.2431(5) _cell_angle_alpha 87.1914(15) _cell_angle_beta 80.8572(17) _cell_angle_gamma 87.1666(17) _cell_volume 3520.38(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 21423 _cell_measurement_temperature 100 _cell_measurement_theta_max 29.4056 _cell_measurement_theta_min 3.3676 _exptl_absorpt_coefficient_mu 0.623 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_correction_T_min 0.7165 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1498 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_special_details ? _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_unetI/netI 0.0588 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_number 47502 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 29.47 _diffrn_reflns_theta_min 3.37 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 10.3756 _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.871 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 38.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 11.5445 -37.0000 30.0000 184 #__ type_ start__ end____ width___ exp.time_ 2 omega -19.00 74.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 11.5445 77.0000 -60.0000 186 #__ type_ start__ end____ width___ exp.time_ 3 omega 5.00 32.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 11.5445 77.0000 30.0000 54 #__ type_ start__ end____ width___ exp.time_ 4 omega -15.00 86.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 11.5445 37.0000 -150.0000 202 #__ type_ start__ end____ width___ exp.time_ 5 omega -65.00 12.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 11.5445 -37.0000 -90.0000 154 #__ type_ start__ end____ width___ exp.time_ 6 omega -67.00 45.00 0.5000 30.0000 omega____ theta____ kappa____ phi______ frames - 11.5445 -77.0000 -150.0000 224 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0698572 _diffrn_orient_matrix_UB_12 0.0212518 _diffrn_orient_matrix_UB_13 -0.0050069 _diffrn_orient_matrix_UB_21 -0.0415594 _diffrn_orient_matrix_UB_22 -0.0317251 _diffrn_orient_matrix_UB_23 0.0165388 _diffrn_orient_matrix_UB_31 5.32e-05 _diffrn_orient_matrix_UB_32 0.0289863 _diffrn_orient_matrix_UB_33 0.019951 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'fine-focus sealed tube' _reflns_number_gt 11860 _reflns_number_total 17063 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.620 _refine_diff_density_min -1.008 _refine_diff_density_rms 0.084 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 889 _refine_ls_number_reflns 17063 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0502 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0759P)^2^+0.7291P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1358 _refine_ls_wR_factor_ref 0.1444 _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. The solvate methanol molecules in this case are just reasonable placeholders to account for the electron density in the clathrate channels. We tried to refine their populations but the refinement does not converge well (big G/Uij correlations) and we used reasonable arbitrary values instead. The hydrogen atoms were put in geometrically calculated positions with Uiso = 1.2 Uiso/eq of an adjacent atom (1.5 Uiso/eq for methyl groups) and refined within a riding model using appropriate fixed distances to the adjacent atoms. The methyl hydrogens' positions were optimized rotationally to fit the residual electron density The hydrogens on the heavily disordered methanol molecule were not localized. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.30818(4) 0.33425(2) 0.148119(12) 0.01287(9) Uani 1 1 d . . . Cl1 Cl 0.10679(7) 0.33725(4) 0.10210(2) 0.01982(14) Uani 1 1 d . . . N1 N 0.5019(2) 0.33130(13) 0.19032(7) 0.0119(4) Uani 1 1 d . . . N11 N 0.1878(2) 0.42481(14) 0.21120(7) 0.0169(4) Uani 1 1 d . . . N12 N 0.2399(2) 0.41293(14) 0.25629(7) 0.0166(4) Uani 1 1 d . . . N21 N 0.2230(3) 0.22863(14) 0.21006(8) 0.0187(5) Uani 1 1 d . . . N22 N 0.2276(2) 0.25316(14) 0.25785(8) 0.0177(5) Uani 1 1 d . . . N31 N 0.4682(2) 0.24633(13) 0.09549(7) 0.0143(4) Uani 1 1 d . . . N32 N 0.6192(2) 0.26829(14) 0.08613(7) 0.0135(4) Uani 1 1 d . . . N41 N 0.4449(2) 0.44118(13) 0.10154(7) 0.0125(4) Uani 1 1 d . . . N42 N 0.6011(2) 0.42918(13) 0.09496(7) 0.0131(4) Uani 1 1 d . . . C1 C 0.3171(3) 0.32751(17) 0.26708(9) 0.0165(5) Uani 1 1 d . . . H1 H 0.3223 0.3247 0.3028 0.020 Uiso 1 1 calc R . . C2 C 0.4798(3) 0.32095(16) 0.24027(9) 0.0149(5) Uani 1 1 d . . . C3 C 0.5989(3) 0.30865(17) 0.26744(9) 0.0175(5) Uani 1 1 d . . . H3 H 0.5792 0.3012 0.3019 0.021 Uiso 1 1 calc R . . C4 C 0.7482(3) 0.30764(18) 0.24252(10) 0.0197(6) Uani 1 1 d . . . H4 H 0.8306 0.2999 0.2599 0.024 Uiso 1 1 calc R . . C5 C 0.7721(3) 0.31846(16) 0.19103(9) 0.0160(5) Uani 1 1 d . . . H5 H 0.8711 0.3180 0.1733 0.019 Uiso 1 1 calc R . . C6 C 0.6474(3) 0.32995(15) 0.16647(9) 0.0127(5) Uani 1 1 d . . . C7 C 0.6707(3) 0.34392(16) 0.11050(9) 0.0130(5) Uani 1 1 d . . . H7 H 0.7813 0.3469 0.0994 0.016 Uiso 1 1 calc R . . C10 C -0.0047(3) 0.52743(19) 0.17804(10) 0.0246(6) Uani 1 1 d . . . H10d H 0.0208 0.4902 0.1498 0.037 Uiso 1 1 calc R . . H10e H 0.0199 0.5887 0.1683 0.037 Uiso 1 1 calc R . . H10f H -0.1123 0.5249 0.1904 0.037 Uiso 1 1 calc R . . C11 C 0.0844(3) 0.49420(17) 0.21767(10) 0.0185(5) Uani 1 1 d . . . C12 C 0.0716(3) 0.52657(17) 0.26628(10) 0.0203(6) Uani 1 1 d . . . C13 C 0.1696(3) 0.47302(17) 0.28983(9) 0.0194(6) Uani 1 1 d . . . C14 C 0.2058(4) 0.4752(2) 0.34144(10) 0.0275(6) Uani 1 1 d . . . H14d H 0.1665 0.4230 0.3605 0.041 Uiso 1 1 calc R . . H14e H 0.1593 0.5289 0.3567 0.041 Uiso 1 1 calc R . . H14f H 0.3148 0.4753 0.3402 0.041 Uiso 1 1 calc R . . C15 C -0.0292(4) 0.60389(19) 0.28721(11) 0.0303(7) Uani 1 1 d . . . H15d H -0.0514 0.6447 0.2606 0.045 Uiso 1 1 calc R . . H15e H 0.0221 0.6352 0.3094 0.045 Uiso 1 1 calc R . . H15f H -0.1231 0.5814 0.3051 0.045 Uiso 1 1 calc R . . C20 C 0.0788(4) 0.1188(2) 0.17207(11) 0.0324(7) Uani 1 1 d . . . H20d H 0.0381 0.1619 0.1496 0.049 Uiso 1 1 calc R . . H20e H 0.0043 0.0745 0.1836 0.049 Uiso 1 1 calc R . . H20f H 0.1702 0.0895 0.1551 0.049 Uiso 1 1 calc R . . C21 C 0.1161(3) 0.16622(18) 0.21540(10) 0.0199(6) Uani 1 1 d . . . C22 C 0.0498(3) 0.15287(17) 0.26540(10) 0.0211(6) Uani 1 1 d . . . C23 C 0.1213(3) 0.20997(18) 0.29160(10) 0.0213(6) Uani 1 1 d . . . C24 C 0.0917(4) 0.2303(2) 0.34544(10) 0.0347(8) Uani 1 1 d . . . H24d H 0.0303 0.2854 0.3499 0.052 Uiso 1 1 calc R . . H24e H 0.1874 0.2369 0.3570 0.052 Uiso 1 1 calc R . . H24f H 0.0382 0.1817 0.3641 0.052 Uiso 1 1 calc R . . C25 C -0.0726(3) 0.08919(19) 0.28673(12) 0.0300(7) Uani 1 1 d . . . H25d H -0.1636 0.1232 0.3003 0.045 Uiso 1 1 calc R . . H25e H -0.0376 0.0513 0.3126 0.045 Uiso 1 1 calc R . . H25f H -0.0949 0.0523 0.2610 0.045 Uiso 1 1 calc R . . C30 C 0.3089(3) 0.14454(19) 0.05635(11) 0.0251(6) Uani 1 1 d . . . H30d H 0.3020 0.1415 0.0217 0.038 Uiso 1 1 calc R . . H30e H 0.2246 0.1813 0.0723 0.038 Uiso 1 1 calc R . . H30f H 0.3056 0.0848 0.0716 0.038 Uiso 1 1 calc R . . C31 C 0.4564(3) 0.18522(17) 0.06183(9) 0.0177(5) Uani 1 1 d . . . C32 C 0.5978(3) 0.16755(18) 0.03160(9) 0.0196(6) Uani 1 1 d . . . C33 C 0.6995(3) 0.22239(17) 0.04709(9) 0.0167(5) Uani 1 1 d . . . C34 C 0.8643(3) 0.2348(2) 0.02800(10) 0.0247(6) Uani 1 1 d . . . H34d H 0.9246 0.2125 0.0527 0.037 Uiso 1 1 calc R . . H34e H 0.8810 0.2978 0.0207 0.037 Uiso 1 1 calc R . . H34f H 0.8937 0.2020 -0.0018 0.037 Uiso 1 1 calc R . . C35 C 0.6268(4) 0.1028(2) -0.00977(11) 0.0319(7) Uani 1 1 d . . . H35d H 0.6304 0.0420 0.0040 0.048 Uiso 1 1 calc R . . H35e H 0.7228 0.1150 -0.0303 0.048 Uiso 1 1 calc R . . H35f H 0.5458 0.1100 -0.0295 0.048 Uiso 1 1 calc R . . C40 C 0.2633(3) 0.55492(18) 0.07040(10) 0.0200(6) Uani 1 1 d . . . H40d H 0.1902 0.5091 0.0801 0.030 Uiso 1 1 calc R . . H40e H 0.2611 0.5744 0.0364 0.030 Uiso 1 1 calc R . . H40f H 0.2379 0.6054 0.0914 0.030 Uiso 1 1 calc R . . C41 C 0.4182(3) 0.51783(16) 0.07563(8) 0.0140(5) Uani 1 1 d . . . C42 C 0.5565(3) 0.55565(17) 0.05297(9) 0.0161(5) Uani 1 1 d . . . C43 C 0.6712(3) 0.49735(17) 0.06548(9) 0.0159(5) Uani 1 1 d . . . C44 C 0.8407(3) 0.5028(2) 0.05250(11) 0.0253(6) Uani 1 1 d . . . H44d H 0.8839 0.5099 0.0822 0.038 Uiso 1 1 calc R . . H44e H 0.8645 0.5537 0.0299 0.038 Uiso 1 1 calc R . . H44f H 0.8830 0.4484 0.0371 0.038 Uiso 1 1 calc R . . C45 C 0.5715(4) 0.64103(19) 0.02178(11) 0.0271(6) Uani 1 1 d . . . H45d H 0.5269 0.6347 -0.0077 0.041 Uiso 1 1 calc R . . H45e H 0.6779 0.6536 0.0126 0.041 Uiso 1 1 calc R . . H45f H 0.5193 0.6899 0.0403 0.041 Uiso 1 1 calc R . . Fe1A Fe 0.19956(4) 0.85491(2) 0.355784(12) 0.01222(9) Uani 1 1 d . . . Cl1A Cl 0.40074(7) 0.86440(4) 0.40084(2) 0.01803(13) Uani 1 1 d . . . N1A N 0.0114(2) 0.84892(13) 0.31164(7) 0.0113(4) Uani 1 1 d . . . N11a N 0.2961(2) 0.94225(14) 0.28762(7) 0.0149(4) Uani 1 1 d . . . N12a N 0.2901(2) 0.90890(14) 0.24174(7) 0.0153(4) Uani 1 1 d . . . N21a N 0.3256(2) 0.74986(14) 0.30473(8) 0.0166(4) Uani 1 1 d . . . N22a N 0.2856(2) 0.74918(14) 0.25778(7) 0.0153(4) Uani 1 1 d . . . N31a N 0.0422(2) 0.76427(13) 0.40659(7) 0.0139(4) Uani 1 1 d . . . N32a N -0.1099(2) 0.79130(13) 0.41590(7) 0.0123(4) Uani 1 1 d . . . N41a N 0.0454(2) 0.95819(13) 0.40222(7) 0.0128(4) Uani 1 1 d . . . N42a N -0.1097(2) 0.95245(13) 0.40282(7) 0.0126(4) Uani 1 1 d . . . C1a C 0.2070(3) 0.82846(16) 0.23828(9) 0.0147(5) Uani 1 1 d . . . H1a H 0.2072 0.8198 0.2028 0.018 Uiso 1 1 calc R . . C2a C 0.0410(3) 0.84003(16) 0.26238(9) 0.0137(5) Uani 1 1 d . . . C3a C -0.0739(3) 0.84079(18) 0.23294(9) 0.0179(5) Uani 1 1 d . . . H3a H -0.0492 0.8346 0.1988 0.022 Uiso 1 1 calc R . . C4a C -0.2248(3) 0.85074(18) 0.25500(9) 0.0205(6) Uani 1 1 d . . . H4a H -0.3035 0.8520 0.2360 0.025 Uiso 1 1 calc R . . C5a C -0.2569(3) 0.85886(17) 0.30629(9) 0.0157(5) Uani 1 1 d . . . H5a H -0.3576 0.8649 0.3224 0.019 Uiso 1 1 calc R . . C6a C -0.1358(3) 0.85777(15) 0.33295(9) 0.0119(5) Uani 1 1 d . . . C7a C -0.1679(3) 0.86849(16) 0.38858(8) 0.0121(5) Uani 1 1 d . . . H7a H -0.2795 0.8720 0.3983 0.015 Uiso 1 1 calc R . . C10a C 0.4339(3) 1.06280(19) 0.31893(10) 0.0228(6) Uani 1 1 d . . . H10a H 0.3701 1.0463 0.3496 0.034 Uiso 1 1 calc R . . H10b H 0.4168 1.1259 0.3110 0.034 Uiso 1 1 calc R . . H10c H 0.5395 1.0511 0.3223 0.034 Uiso 1 1 calc R . . C11a C 0.3954(3) 1.00853(16) 0.27826(9) 0.0159(5) Uani 1 1 d . . . C12a C 0.4545(3) 1.01718(17) 0.22712(10) 0.0188(5) Uani 1 1 d . . . C13a C 0.3866(3) 0.95231(17) 0.20490(9) 0.0187(5) Uani 1 1 d . . . C14a C 0.4054(4) 0.9292(2) 0.15138(10) 0.0320(7) Uani 1 1 d . . . H14a H 0.4655 0.8737 0.1466 0.048 Uiso 1 1 calc R . . H14b H 0.4564 0.9768 0.1310 0.048 Uiso 1 1 calc R . . H14c H 0.3065 0.9222 0.1421 0.048 Uiso 1 1 calc R . . C15a C 0.5689(3) 1.08309(19) 0.20182(10) 0.0255(6) Uani 1 1 d . . . H15a H 0.6567 1.0505 0.1848 0.038 Uiso 1 1 calc R . . H15b H 0.6001 1.1197 0.2262 0.038 Uiso 1 1 calc R . . H15c H 0.5228 1.1211 0.1782 0.038 Uiso 1 1 calc R . . C20a C 0.5133(3) 0.65969(19) 0.34877(10) 0.0239(6) Uani 1 1 d . . . H20a H 0.4835 0.6018 0.3635 0.036 Uiso 1 1 calc R . . H20b H 0.4881 0.7049 0.3731 0.036 Uiso 1 1 calc R . . H20c H 0.6217 0.6578 0.3373 0.036 Uiso 1 1 calc R . . C21a C 0.4303(3) 0.68233(17) 0.30603(10) 0.0184(5) Uani 1 1 d . . . C22a C 0.4557(3) 0.63713(17) 0.26060(10) 0.0196(6) Uani 1 1 d . . . C23a C 0.3653(3) 0.68204(17) 0.23045(9) 0.0178(5) Uani 1 1 d . . . C24a C 0.3446(4) 0.6653(2) 0.17848(10) 0.0266(6) Uani 1 1 d . . . H24a H 0.4047 0.7061 0.1558 0.040 Uiso 1 1 calc R . . H24b H 0.2384 0.6747 0.1753 0.040 Uiso 1 1 calc R . . H24c H 0.3773 0.6041 0.1709 0.040 Uiso 1 1 calc R . . C25a C 0.5623(4) 0.5565(2) 0.24911(12) 0.0295(7) Uani 1 1 d . . . H25a H 0.5397 0.5293 0.2200 0.044 Uiso 1 1 calc R . . H25b H 0.5493 0.5135 0.2768 0.044 Uiso 1 1 calc R . . H25c H 0.6662 0.5753 0.2432 0.044 Uiso 1 1 calc R . . C30a C 0.2092(3) 0.65316(18) 0.44575(11) 0.0238(6) Uani 1 1 d . . . H30a H 0.2126 0.5934 0.4334 0.036 Uiso 1 1 calc R . . H30b H 0.2228 0.6494 0.4801 0.036 Uiso 1 1 calc R . . H30c H 0.2896 0.6871 0.4267 0.036 Uiso 1 1 calc R . . C31a C 0.0585(3) 0.69889(16) 0.44120(9) 0.0149(5) Uani 1 1 d . . . C32a C -0.0813(3) 0.68428(16) 0.47272(9) 0.0159(5) Uani 1 1 d . . . C33a C -0.1863(3) 0.74518(16) 0.45596(9) 0.0146(5) Uani 1 1 d . . . C34a C -0.3515(3) 0.76217(19) 0.47564(10) 0.0209(6) Uani 1 1 d . . . H34a H -0.3721 0.8258 0.4795 0.031 Uiso 1 1 calc R . . H34b H -0.3764 0.7306 0.5073 0.031 Uiso 1 1 calc R . . H34c H -0.4127 0.7410 0.4528 0.031 Uiso 1 1 calc R . . C35a C -0.1083(4) 0.6189(2) 0.51664(11) 0.0311(7) Uani 1 1 d . . . H35a H -0.1375 0.5623 0.5061 0.047 Uiso 1 1 calc R . . H35b H -0.1887 0.6428 0.5410 0.047 Uiso 1 1 calc R . . H35c H -0.0160 0.6096 0.5309 0.047 Uiso 1 1 calc R . . C40a C 0.2049(3) 1.06215(18) 0.44048(9) 0.0187(5) Uani 1 1 d . . . H40a H 0.2843 1.0164 0.4322 0.028 Uiso 1 1 calc R . . H40b H 0.1931 1.0726 0.4754 0.028 Uiso 1 1 calc R . . H40c H 0.2322 1.1171 0.4218 0.028 Uiso 1 1 calc R . . C41a C 0.0579(3) 1.03169(16) 0.42808(9) 0.0145(5) Uani 1 1 d . . . C42a C -0.0870(3) 1.07387(17) 0.44399(9) 0.0159(5) Uani 1 1 d . . . C43a C -0.1917(3) 1.02117(16) 0.42801(9) 0.0144(5) Uani 1 1 d . . . C44a C -0.3613(3) 1.03462(19) 0.43483(10) 0.0207(6) Uani 1 1 d . . . H44a H -0.3879 1.0913 0.4192 0.031 Uiso 1 1 calc R . . H44b H -0.4012 1.0348 0.4697 0.031 Uiso 1 1 calc R . . H44c H -0.4042 0.9865 0.4200 0.031 Uiso 1 1 calc R . . C45a C -0.1202(3) 1.15719(19) 0.47283(10) 0.0246(6) Uani 1 1 d . . . H45a H -0.2242 1.1783 0.4720 0.037 Uiso 1 1 calc R . . H45b H -0.0519 1.2031 0.4584 0.037 Uiso 1 1 calc R . . H45c H -0.1059 1.1439 0.5067 0.037 Uiso 1 1 calc R . . Cl2 Cl 0.44941(11) 0.27828(6) 0.39090(3) 0.0421(2) Uani 1 1 d . . . Cl2A Cl 1.11033(10) 0.79938(7) 0.11148(3) 0.0440(2) Uani 1 1 d . . . O1S O 0.4408(6) 0.4754(3) 0.42938(19) 0.0444(12) Uani 0.50 1 d P A -1 C1S C 0.5052(12) 0.4806(6) 0.4738(3) 0.064(2) Uani 0.50 1 d P A -1 O1SA O 0.8556(6) 0.9501(3) 0.12523(16) 0.1119(15) Uani 1 1 d . . . C1SA C 0.8521(9) 0.9873(4) 0.0790(2) 0.115(3) Uani 1 1 d . . . O2S O 0.7792(7) 0.3640(11) 0.3895(5) 0.359(8) Uani 1 1 d . . . C2S C 0.733(2) 0.4350(6) 0.3713(5) 0.271(9) Uani 1 1 d . . . O2SA O 0.8566(8) 0.7061(6) 0.0830(3) 0.118(4) Uani 0.50 1 d P B 1 C2SA C 0.743(2) 0.7170(12) 0.1193(5) 0.076(6) Uani 0.50 1 d P B 1 O2SB O 0.6765(12) 0.7843(6) 0.1422(4) 0.121(3) Uani 0.50 1 d P C 2 C2SB C 0.7410(15) 0.7093(9) 0.1444(6) 0.069(4) Uani 0.50 1 d P C 2 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 0.00892(18) 0.01607(19) 0.01336(18) 0.00136(13) -0.00124(14) -0.00149(13) Cl1 0.0111(3) 0.0251(3) 0.0243(3) -0.0010(3) -0.0056(2) -0.0022(2) N1 0.0123(10) 0.0110(10) 0.0119(10) 0.0017(8) -0.0011(8) -0.0005(7) N11 0.0140(11) 0.0213(12) 0.0140(10) 0.0024(8) 0.0002(9) 0.0016(8) N12 0.0150(11) 0.0200(11) 0.0136(10) 0.0001(8) 0.0007(9) 0.0011(8) N21 0.0174(12) 0.0189(11) 0.0187(11) 0.0018(9) 0.0002(9) -0.0030(9) N22 0.0167(11) 0.0198(11) 0.0150(10) 0.0048(8) 0.0014(9) -0.0019(8) N31 0.0129(11) 0.0140(11) 0.0163(10) 0.0003(8) -0.0029(8) -0.0025(8) N32 0.0105(10) 0.0180(11) 0.0119(10) -0.0007(8) -0.0009(8) -0.0010(8) N41 0.0077(10) 0.0164(11) 0.0128(10) 0.0000(8) -0.0004(8) 0.0008(8) N42 0.0096(10) 0.0161(11) 0.0133(10) 0.0030(8) -0.0015(8) -0.0027(8) C1 0.0156(13) 0.0190(13) 0.0137(12) 0.0021(10) 0.0003(10) 0.0001(10) C2 0.0174(13) 0.0127(12) 0.0139(12) 0.0003(9) -0.0008(10) 0.0004(9) C3 0.0210(14) 0.0198(13) 0.0113(12) 0.0010(10) -0.0026(10) 0.0025(10) C4 0.0175(14) 0.0218(14) 0.0212(13) -0.0016(11) -0.0085(11) 0.0041(10) C5 0.0126(13) 0.0174(13) 0.0176(12) -0.0008(10) -0.0020(10) 0.0017(9) C6 0.0132(12) 0.0090(11) 0.0158(12) -0.0005(9) -0.0016(10) -0.0012(9) C7 0.0092(12) 0.0166(12) 0.0131(11) 0.0005(9) -0.0016(9) 0.0003(9) C10 0.0180(14) 0.0264(15) 0.0275(15) -0.0009(12) -0.0004(12) 0.0071(11) C11 0.0129(13) 0.0158(13) 0.0252(14) -0.0006(10) 0.0017(11) -0.0002(10) C12 0.0175(14) 0.0166(13) 0.0242(14) -0.0015(10) 0.0053(11) -0.0012(10) C13 0.0204(14) 0.0181(13) 0.0181(13) -0.0026(10) 0.0032(11) -0.0028(10) C14 0.0337(17) 0.0272(16) 0.0216(14) -0.0069(12) -0.0027(12) -0.0001(12) C15 0.0334(18) 0.0199(15) 0.0349(17) -0.0039(12) 0.0024(14) 0.0046(12) C20 0.0349(18) 0.0317(17) 0.0306(16) 0.0004(13) -0.0005(14) -0.0159(13) C21 0.0141(13) 0.0190(14) 0.0254(14) 0.0038(11) -0.0004(11) -0.0017(10) C22 0.0163(14) 0.0164(13) 0.0278(14) 0.0083(11) 0.0016(11) 0.0023(10) C23 0.0176(14) 0.0198(14) 0.0228(14) 0.0085(11) 0.0045(11) 0.0020(10) C24 0.044(2) 0.0352(18) 0.0205(15) 0.0072(12) 0.0087(14) -0.0121(14) C25 0.0263(16) 0.0230(15) 0.0370(17) 0.0085(12) 0.0049(13) -0.0063(12) C30 0.0242(15) 0.0201(14) 0.0314(15) -0.0066(12) -0.0019(12) -0.0081(11) C31 0.0203(14) 0.0125(12) 0.0202(13) -0.0005(10) -0.0020(11) -0.0038(10) C32 0.0221(14) 0.0194(14) 0.0171(13) -0.0011(10) -0.0017(11) -0.0018(10) C33 0.0174(13) 0.0169(13) 0.0152(12) -0.0006(10) -0.0016(10) 0.0025(10) C34 0.0170(14) 0.0338(16) 0.0228(14) -0.0115(12) 0.0006(11) 0.0018(11) C35 0.0313(17) 0.0314(17) 0.0322(16) -0.0151(13) 0.0025(13) -0.0056(13) C40 0.0171(14) 0.0197(14) 0.0227(14) 0.0017(10) -0.0040(11) 0.0034(10) C41 0.0168(13) 0.0152(12) 0.0104(11) -0.0045(9) -0.0026(10) 0.0008(9) C42 0.0190(13) 0.0154(13) 0.0143(12) 0.0001(9) -0.0034(10) -0.0021(10) C43 0.0174(13) 0.0177(13) 0.0124(12) 0.0032(9) -0.0018(10) -0.0047(10) C44 0.0152(14) 0.0310(16) 0.0283(15) 0.0098(12) -0.0010(12) -0.0070(11) C45 0.0299(17) 0.0213(15) 0.0275(15) 0.0080(11) -0.0002(13) 0.0000(12) Fe1A 0.00892(18) 0.01536(19) 0.01267(17) 0.00014(13) -0.00243(13) -0.00163(13) Cl1A 0.0125(3) 0.0227(3) 0.0202(3) -0.0010(2) -0.0066(2) -0.0009(2) N1A 0.0119(10) 0.0112(10) 0.0113(9) 0.0008(7) -0.0031(8) -0.0017(7) N11a 0.0147(11) 0.0176(11) 0.0126(10) -0.0003(8) -0.0021(8) -0.0025(8) N12a 0.0156(11) 0.0166(11) 0.0136(10) 0.0004(8) -0.0011(8) -0.0031(8) N21a 0.0149(11) 0.0193(11) 0.0153(10) -0.0012(8) -0.0017(9) 0.0018(8) N22a 0.0121(11) 0.0202(11) 0.0138(10) -0.0027(8) -0.0027(8) 0.0016(8) N31a 0.0117(11) 0.0136(10) 0.0171(10) -0.0011(8) -0.0044(8) -0.0011(8) N32a 0.0100(10) 0.0144(10) 0.0126(10) 0.0016(8) -0.0027(8) -0.0005(8) N41a 0.0094(10) 0.0154(11) 0.0142(10) 0.0011(8) -0.0031(8) -0.0031(8) N42a 0.0093(10) 0.0143(10) 0.0143(10) -0.0019(8) -0.0011(8) -0.0032(8) C1a 0.0134(12) 0.0173(13) 0.0135(12) 0.0002(9) -0.0025(10) -0.0022(9) C2a 0.0168(13) 0.0125(12) 0.0118(11) 0.0005(9) -0.0027(10) -0.0009(9) C3a 0.0182(14) 0.0250(14) 0.0111(12) -0.0016(10) -0.0031(10) -0.0018(10) C4a 0.0188(14) 0.0260(15) 0.0185(13) -0.0003(11) -0.0086(11) -0.0008(11) C5a 0.0111(12) 0.0202(13) 0.0164(12) 0.0017(10) -0.0044(10) -0.0023(9) C6a 0.0131(12) 0.0070(11) 0.0159(12) 0.0020(9) -0.0038(10) -0.0018(8) C7a 0.0092(12) 0.0151(12) 0.0122(11) 0.0004(9) -0.0021(9) -0.0023(9) C10a 0.0232(15) 0.0216(14) 0.0237(14) 0.0006(11) -0.0022(12) -0.0086(11) C11a 0.0138(13) 0.0139(12) 0.0197(13) 0.0024(10) -0.0033(10) 0.0012(9) C12a 0.0151(13) 0.0181(13) 0.0207(13) 0.0023(10) 0.0027(11) 0.0009(10) C13a 0.0185(14) 0.0175(13) 0.0175(13) 0.0040(10) 0.0031(10) 0.0008(10) C14a 0.047(2) 0.0304(17) 0.0159(13) 0.0014(12) 0.0062(13) -0.0124(14) C15a 0.0279(16) 0.0209(14) 0.0251(14) 0.0013(11) 0.0049(12) -0.0079(11) C20a 0.0180(14) 0.0271(15) 0.0263(14) -0.0028(11) -0.0053(11) 0.0081(11) C21a 0.0126(13) 0.0196(13) 0.0217(13) 0.0003(10) 0.0001(10) 0.0019(10) C22a 0.0166(13) 0.0169(13) 0.0245(14) -0.0048(10) 0.0008(11) -0.0010(10) C23a 0.0158(13) 0.0161(13) 0.0202(13) -0.0039(10) 0.0025(10) -0.0029(10) C24a 0.0313(17) 0.0250(15) 0.0242(14) -0.0093(12) -0.0041(12) -0.0028(12) C25a 0.0263(16) 0.0244(16) 0.0359(17) -0.0062(13) -0.0003(13) 0.0080(12) C30a 0.0220(15) 0.0191(14) 0.0282(15) 0.0037(11) -0.0002(12) 0.0042(11) C31a 0.0197(13) 0.0117(12) 0.0134(12) -0.0003(9) -0.0030(10) -0.0019(9) C32a 0.0184(13) 0.0144(12) 0.0152(12) 0.0006(9) -0.0031(10) -0.0031(10) C33a 0.0166(13) 0.0144(12) 0.0130(11) 0.0019(9) -0.0026(10) -0.0040(9) C34a 0.0142(13) 0.0302(15) 0.0172(13) 0.0079(11) -0.0014(11) -0.0025(11) C35a 0.0277(17) 0.0320(17) 0.0298(16) 0.0124(13) 0.0025(13) 0.0012(13) C40a 0.0165(13) 0.0226(14) 0.0184(13) -0.0004(10) -0.0051(10) -0.0072(10) C41a 0.0164(13) 0.0158(12) 0.0112(11) 0.0010(9) -0.0012(10) -0.0047(9) C42a 0.0180(13) 0.0172(13) 0.0124(12) -0.0004(9) -0.0014(10) -0.0022(10) C43a 0.0156(13) 0.0168(13) 0.0103(11) 0.0002(9) -0.0009(10) -0.0007(9) C44a 0.0127(13) 0.0251(14) 0.0239(14) -0.0061(11) -0.0005(11) 0.0005(10) C45a 0.0224(15) 0.0262(15) 0.0245(14) -0.0083(11) 0.0023(12) -0.0053(11) Cl2 0.0631(6) 0.0456(5) 0.0156(3) 0.0022(3) -0.0002(4) -0.0057(4) Cl2A 0.0416(5) 0.0690(6) 0.0203(4) -0.0048(4) -0.0056(3) 0.0144(4) O1S 0.042(3) 0.034(3) 0.059(3) 0.003(2) -0.018(2) 0.004(2) C1S 0.082(7) 0.051(5) 0.068(6) -0.014(4) -0.037(5) 0.001(4) O1SA 0.141(4) 0.098(3) 0.094(3) -0.006(2) -0.019(3) 0.037(3) C1SA 0.185(7) 0.090(4) 0.061(3) 0.027(3) -0.026(4) 0.061(4) O2S 0.041(4) 0.62(2) 0.403(16) 0.049(16) -0.006(6) -0.014(7) C2S 0.54(3) 0.063(5) 0.217(11) 0.094(6) -0.089(14) -0.085(9) O2SA 0.068(5) 0.148(7) 0.140(7) -0.114(6) 0.026(5) -0.047(5) C2SA 0.065(8) 0.080(10) 0.078(9) -0.051(8) 0.033(7) -0.037(7) O2SB 0.128(8) 0.085(6) 0.157(9) 0.005(6) -0.039(7) -0.029(6) C2SB 0.025(5) 0.038(6) 0.135(14) -0.006(8) 0.010(8) 0.014(4) _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 Cl1 2.3332(7) . ? Fe1 N1 2.207(2) . ? Fe1 N11 2.322(2) . ? Fe1 N21 2.307(2) . ? Fe1 N31 2.261(2) . ? Fe1 N41 2.2566(19) . ? N1 C2 1.346(3) . ? N1 C6 1.346(3) . ? N11 C11 1.342(3) . ? N12 N11 1.380(3) . ? N12 C1 1.449(3) . ? N12 C13 1.364(3) . ? N21 C21 1.342(3) . ? N22 N21 1.376(3) . ? N22 C1 1.443(3) . ? N22 C23 1.366(3) . ? N31 C31 1.339(3) . ? N32 N31 1.372(3) . ? N32 C7 1.458(3) . ? N32 C33 1.372(3) . ? N41 C41 1.339(3) . ? N42 N41 1.368(3) . ? N42 C7 1.452(3) . ? N42 C43 1.369(3) . ? C1 H1 0.9800 . ? C2 C1 1.508(3) . ? C2 C3 1.381(4) . ? C3 H3 0.9300 . ? C3 C4 1.385(4) . ? C4 H4 0.9300 . ? C4 C5 1.388(4) . ? C5 H5 0.9300 . ? C5 C6 1.378(4) . ? C6 C7 1.511(3) . ? C7 H7 0.9800 . ? C10 H10d 0.9600 . ? C10 H10e 0.9600 . ? C10 H10f 0.9600 . ? C11 C10 1.486(4) . ? C12 C11 1.416(4) . ? C12 C15 1.496(4) . ? C13 C12 1.361(4) . ? C13 C14 1.493(4) . ? C14 H14d 0.9600 . ? C14 H14e 0.9600 . ? C14 H14f 0.9600 . ? C15 H15d 0.9600 . ? C15 H15e 0.9600 . ? C15 H15f 0.9600 . ? C20 H20d 0.9600 . ? C20 H20e 0.9600 . ? C20 H20f 0.9600 . ? C21 C20 1.492(4) . ? C22 C21 1.403(4) . ? C22 C25 1.500(4) . ? C23 C22 1.372(4) . ? C23 C24 1.491(4) . ? C24 H24d 0.9600 . ? C24 H24e 0.9600 . ? C24 H24f 0.9600 . ? C25 H25d 0.9600 . ? C25 H25e 0.9600 . ? C25 H25f 0.9600 . ? C30 H30d 0.9600 . ? C30 H30e 0.9600 . ? C30 H30f 0.9600 . ? C31 C30 1.496(4) . ? C32 C31 1.405(4) . ? C32 C35 1.499(4) . ? C33 C32 1.369(4) . ? C33 C34 1.485(4) . ? C34 H34d 0.9600 . ? C34 H34e 0.9600 . ? C34 H34f 0.9600 . ? C35 H35d 0.9600 . ? C35 H35e 0.9600 . ? C35 H35f 0.9600 . ? C40 H40d 0.9600 . ? C40 H40e 0.9600 . ? C40 H40f 0.9600 . ? C41 C40 1.476(4) . ? C42 C41 1.409(3) . ? C42 C45 1.489(4) . ? C43 C42 1.374(4) . ? C43 C44 1.490(4) . ? C44 H44d 0.9600 . ? C44 H44e 0.9600 . ? C44 H44f 0.9600 . ? C45 H45d 0.9600 . ? C45 H45e 0.9600 . ? C45 H45f 0.9600 . ? Fe1A Cl1A 2.3303(7) . ? Fe1A N1A 2.211(2) . ? Fe1A N11a 2.286(2) . ? Fe1A N21a 2.270(2) . ? Fe1A N31a 2.247(2) . ? Fe1A N41a 2.289(2) . ? N1A C2a 1.338(3) . ? N1A C6a 1.341(3) . ? N11a C11a 1.339(3) . ? N12a N11a 1.376(3) . ? N12a C1a 1.446(3) . ? N12a C13a 1.367(3) . ? N21a C21a 1.333(3) . ? N22a N21a 1.381(3) . ? N22a C1a 1.457(3) . ? N22a C23a 1.371(3) . ? N31a C31a 1.338(3) . ? N32a N31a 1.373(3) . ? N32a C7a 1.451(3) . ? N32a C33a 1.362(3) . ? N41a C41a 1.345(3) . ? N42a N41a 1.376(3) . ? N42a C7a 1.463(3) . ? N42a C43a 1.368(3) . ? C1a H1a 0.9800 . ? C2a C1a 1.515(3) . ? C3a C2a 1.391(4) . ? C3a H3a 0.9300 . ? C4a C3a 1.378(4) . ? C4a H4a 0.9300 . ? C5a C4a 1.391(3) . ? C5a H5a 0.9300 . ? C6a C5a 1.386(3) . ? C6a C7a 1.512(3) . ? C7a H7a 0.9800 . ? C10a H10a 0.9600 . ? C10a H10b 0.9600 . ? C10a H10c 0.9600 . ? C11a C10a 1.492(4) . ? C12a C11a 1.410(4) . ? C12a C15a 1.505(3) . ? C13a C12a 1.372(4) . ? C13a C14a 1.496(4) . ? C14a H14a 0.9600 . ? C14a H14b 0.9600 . ? C14a H14c 0.9600 . ? C15a H15a 0.9600 . ? C15a H15b 0.9600 . ? C15a H15c 0.9600 . ? C20a H20a 0.9600 . ? C20a H20b 0.9600 . ? C20a H20c 0.9600 . ? C21a C20a 1.489(4) . ? C22a C21a 1.418(4) . ? C22a C25a 1.499(4) . ? C23a C22a 1.364(4) . ? C23a C24a 1.491(4) . ? C24a H24a 0.9600 . ? C24a H24b 0.9600 . ? C24a H24c 0.9600 . ? C25a H25a 0.9600 . ? C25a H25b 0.9600 . ? C25a H25c 0.9600 . ? C30a H30a 0.9600 . ? C30a H30b 0.9600 . ? C30a H30c 0.9600 . ? C31a C30a 1.486(4) . ? C32a C31a 1.409(3) . ? C32a C35a 1.499(4) . ? C33a C32a 1.378(4) . ? C33a C34a 1.488(4) . ? C34a H34a 0.9600 . ? C34a H34b 0.9600 . ? C34a H34c 0.9600 . ? C35a H35a 0.9600 . ? C35a H35b 0.9600 . ? C35a H35c 0.9600 . ? C40a H40a 0.9600 . ? C40a H40b 0.9600 . ? C40a H40c 0.9600 . ? C41a C40a 1.491(3) . ? C42a C41a 1.412(4) . ? C42a C45a 1.489(4) . ? C43a C42a 1.375(3) . ? C43a C44a 1.487(4) . ? C44a H44a 0.9600 . ? C44a H44b 0.9600 . ? C44a H44c 0.9600 . ? C45a H45a 0.9600 . ? C45a H45b 0.9600 . ? C45a H45c 0.9600 . ? O1S C1S 1.424(9) . ? O1SA C1SA 1.354(6) . ? O2S C2S 1.223(15) . ? O2SA C2SA 1.301(14) . ? O2SB C2SB 1.229(15) . ? 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 N1 Fe1 Cl1 178.91(5) . . ? N1 Fe1 N11 83.79(7) . . ? N1 Fe1 N21 80.78(7) . . ? N1 Fe1 N31 84.05(7) . . ? N1 Fe1 N41 82.57(7) . . ? N11 Fe1 Cl1 97.12(6) . . ? N21 Fe1 Cl1 99.99(6) . . ? N21 Fe1 N11 77.93(7) . . ? N31 Fe1 Cl1 95.04(6) . . ? N31 Fe1 N11 167.83(8) . . ? N31 Fe1 N21 100.52(7) . . ? N41 Fe1 Cl1 96.69(6) . . ? N41 Fe1 N11 98.21(7) . . ? N41 Fe1 N21 163.22(8) . . ? N41 Fe1 N31 79.76(7) . . ? C2 N1 Fe1 121.40(16) . . ? C2 N1 C6 117.6(2) . . ? C6 N1 Fe1 120.61(15) . . ? N12 N11 Fe1 116.06(15) . . ? C11 N11 Fe1 139.31(18) . . ? C11 N11 N12 104.4(2) . . ? N11 N12 C1 118.1(2) . . ? C13 N12 N11 111.7(2) . . ? C13 N12 C1 127.0(2) . . ? N22 N21 Fe1 115.47(15) . . ? C21 N21 Fe1 134.15(18) . . ? C21 N21 N22 104.3(2) . . ? N21 N22 C1 120.83(19) . . ? C23 N22 N21 111.7(2) . . ? C23 N22 C1 126.6(2) . . ? N32 N31 Fe1 116.83(14) . . ? C31 N31 Fe1 137.47(17) . . ? C31 N31 N32 104.35(19) . . ? N31 N32 C7 120.14(19) . . ? C33 N32 N31 111.90(19) . . ? C33 N32 C7 127.0(2) . . ? N42 N41 Fe1 116.93(14) . . ? C41 N41 Fe1 138.03(16) . . ? C41 N41 N42 105.03(18) . . ? N41 N42 C7 119.90(18) . . ? N41 N42 C43 111.6(2) . . ? C43 N42 C7 127.5(2) . . ? N12 C1 H1 106.9 . . ? N12 C1 C2 112.32(19) . . ? N22 C1 N12 110.4(2) . . ? N22 C1 H1 106.9 . . ? N22 C1 C2 112.9(2) . . ? C2 C1 H1 106.9 . . ? N1 C2 C1 117.5(2) . . ? N1 C2 C3 123.0(2) . . ? C3 C2 C1 119.5(2) . . ? C2 C3 H3 120.5 . . ? C2 C3 C4 119.0(2) . . ? C4 C3 H3 120.5 . . ? C3 C4 H4 120.7 . . ? C3 C4 C5 118.5(2) . . ? C5 C4 H4 120.7 . . ? C4 C5 H5 120.4 . . ? C6 C5 C4 119.2(2) . . ? C6 C5 H5 120.4 . . ? N1 C6 C5 122.8(2) . . ? N1 C6 C7 117.1(2) . . ? C5 C6 C7 120.1(2) . . ? N32 C7 C6 112.29(19) . . ? N32 C7 H7 106.9 . . ? N42 C7 N32 111.41(19) . . ? N42 C7 C6 112.03(19) . . ? N42 C7 H7 106.9 . . ? C6 C7 H7 106.9 . . ? H10d C10 H10e 109.5 . . ? H10d C10 H10f 109.5 . . ? H10e C10 H10f 109.5 . . ? C11 C10 H10d 109.5 . . ? C11 C10 H10e 109.5 . . ? C11 C10 H10f 109.5 . . ? N11 C11 C10 122.1(2) . . ? N11 C11 C12 110.9(2) . . ? C12 C11 C10 127.0(2) . . ? C11 C12 C15 126.8(3) . . ? C13 C12 C11 106.0(2) . . ? C13 C12 C15 127.3(3) . . ? N12 C13 C14 122.6(3) . . ? C12 C13 N12 107.0(2) . . ? C12 C13 C14 130.3(2) . . ? C13 C14 H14d 109.5 . . ? C13 C14 H14e 109.5 . . ? C13 C14 H14f 109.5 . . ? H14d C14 H14e 109.5 . . ? H14d C14 H14f 109.5 . . ? H14e C14 H14f 109.5 . . ? C12 C15 H15d 109.5 . . ? C12 C15 H15e 109.5 . . ? C12 C15 H15f 109.5 . . ? H15d C15 H15e 109.5 . . ? H15d C15 H15f 109.5 . . ? H15e C15 H15f 109.5 . . ? H20d C20 H20e 109.5 . . ? H20d C20 H20f 109.5 . . ? H20e C20 H20f 109.5 . . ? C21 C20 H20d 109.5 . . ? C21 C20 H20e 109.5 . . ? C21 C20 H20f 109.5 . . ? N21 C21 C20 121.9(2) . . ? N21 C21 C22 111.5(2) . . ? C22 C21 C20 126.6(2) . . ? C21 C22 C25 128.0(3) . . ? C23 C22 C21 105.8(2) . . ? C23 C22 C25 126.3(3) . . ? N22 C23 C22 106.7(2) . . ? N22 C23 C24 122.9(2) . . ? C22 C23 C24 130.3(2) . . ? C23 C24 H24d 109.5 . . ? C23 C24 H24e 109.5 . . ? C23 C24 H24f 109.5 . . ? H24d C24 H24e 109.5 . . ? H24d C24 H24f 109.5 . . ? H24e C24 H24f 109.5 . . ? C22 C25 H25d 109.5 . . ? C22 C25 H25e 109.5 . . ? C22 C25 H25f 109.5 . . ? H25d C25 H25e 109.5 . . ? H25d C25 H25f 109.5 . . ? H25e C25 H25f 109.5 . . ? H30d C30 H30e 109.5 . . ? H30d C30 H30f 109.5 . . ? H30e C30 H30f 109.5 . . ? C31 C30 H30d 109.5 . . ? C31 C30 H30e 109.5 . . ? C31 C30 H30f 109.5 . . ? N31 C31 C30 123.5(2) . . ? N31 C31 C32 111.4(2) . . ? C32 C31 C30 125.0(2) . . ? C31 C32 C35 125.9(2) . . ? C33 C32 C31 106.0(2) . . ? C33 C32 C35 128.1(2) . . ? N32 C33 C34 123.5(2) . . ? C32 C33 N32 106.3(2) . . ? C32 C33 C34 130.3(2) . . ? C33 C34 H34d 109.5 . . ? C33 C34 H34e 109.5 . . ? C33 C34 H34f 109.5 . . ? H34d C34 H34e 109.5 . . ? H34d C34 H34f 109.5 . . ? H34e C34 H34f 109.5 . . ? C32 C35 H35d 109.5 . . ? C32 C35 H35e 109.5 . . ? C32 C35 H35f 109.5 . . ? H35d C35 H35e 109.5 . . ? H35d C35 H35f 109.5 . . ? H35e C35 H35f 109.5 . . ? H40d C40 H40e 109.5 . . ? H40d C40 H40f 109.5 . . ? H40e C40 H40f 109.5 . . ? C41 C40 H40d 109.5 . . ? C41 C40 H40e 109.5 . . ? C41 C40 H40f 109.5 . . ? N41 C41 C40 123.8(2) . . ? N41 C41 C42 111.0(2) . . ? C42 C41 C40 125.2(2) . . ? C41 C42 C45 126.1(2) . . ? C43 C42 C41 105.7(2) . . ? C43 C42 C45 128.2(2) . . ? N42 C43 C42 106.6(2) . . ? N42 C43 C44 123.5(2) . . ? C42 C43 C44 129.8(2) . . ? C43 C44 H44d 109.5 . . ? C43 C44 H44e 109.5 . . ? C43 C44 H44f 109.5 . . ? H44d C44 H44e 109.5 . . ? H44d C44 H44f 109.5 . . ? H44e C44 H44f 109.5 . . ? C42 C45 H45d 109.5 . . ? C42 C45 H45e 109.5 . . ? C42 C45 H45f 109.5 . . ? H45d C45 H45e 109.5 . . ? H45d C45 H45f 109.5 . . ? H45e C45 H45f 109.5 . . ? N1A Fe1A Cl1A 178.44(5) . . ? N1A Fe1A N11a 80.35(7) . . ? N1A Fe1A N21a 86.22(7) . . ? N1A Fe1A N31a 80.01(7) . . ? N1A Fe1A N41a 86.34(7) . . ? N11a Fe1A Cl1A 98.12(6) . . ? N11a Fe1A N41a 101.45(7) . . ? N21a Fe1A Cl1A 93.80(6) . . ? N21a Fe1A N11a 78.22(7) . . ? N21a Fe1A N41a 172.50(8) . . ? N31a Fe1A Cl1A 101.53(6) . . ? N31a Fe1A N11a 160.32(8) . . ? N31a Fe1A N21a 99.16(8) . . ? N31a Fe1A N41a 78.59(7) . . ? N41a Fe1A Cl1A 93.67(5) . . ? C2a N1A Fe1A 120.87(16) . . ? C2a N1A C6a 117.8(2) . . ? C6a N1A Fe1A 121.22(15) . . ? N12a N11a Fe1A 116.91(14) . . ? C11a N11a Fe1A 135.81(17) . . ? C11a N11a N12a 104.59(19) . . ? N11a N12a C1a 119.82(19) . . ? C13a N12a N11a 111.6(2) . . ? C13a N12a C1a 127.9(2) . . ? N22a N21a Fe1A 116.06(15) . . ? C21a N21a Fe1A 139.01(17) . . ? C21a N21a N22a 104.9(2) . . ? N21a N22a C1a 119.52(19) . . ? C23a N22a N21a 111.4(2) . . ? C23a N22a C1a 126.3(2) . . ? N32a N31a Fe1A 117.11(14) . . ? C31a N31a Fe1A 135.93(17) . . ? C31a N31a N32a 104.68(19) . . ? N31a N32a C7a 120.54(18) . . ? C33a N32a N31a 111.9(2) . . ? C33a N32a C7a 127.1(2) . . ? N42a N41a Fe1A 115.98(14) . . ? C41a N41a Fe1A 139.29(17) . . ? C41a N41a N42a 104.50(19) . . ? N41a N42a C7a 119.02(19) . . ? C43a N42a N41a 111.81(19) . . ? C43a N42a C7a 127.4(2) . . ? N12a C1a N22a 110.7(2) . . ? N12a C1a H1a 107.1 . . ? N12a C1a C2a 111.4(2) . . ? N22a C1a H1a 107.1 . . ? N22a C1a C2a 113.14(19) . . ? C2a C1a H1a 107.1 . . ? N1A C2a C1a 118.0(2) . . ? N1A C2a C3a 122.6(2) . . ? C3a C2a C1a 119.4(2) . . ? C2a C3a H3a 120.4 . . ? C4a C3a C2a 119.2(2) . . ? C4a C3a H3a 120.4 . . ? C3a C4a H4a 120.7 . . ? C3a C4a C5a 118.6(2) . . ? C5a C4a H4a 120.7 . . ? C4a C5a H5a 120.7 . . ? C6a C5a C4a 118.6(2) . . ? C6a C5a H5a 120.7 . . ? N1A C6a C5a 123.1(2) . . ? N1A C6a C7a 117.4(2) . . ? C5a C6a C7a 119.5(2) . . ? N32a C7a N42a 110.77(19) . . ? N32a C7a C6a 112.26(19) . . ? N32a C7a H7a 107.2 . . ? N42a C7a C6a 111.99(18) . . ? N42a C7a H7a 107.2 . . ? C6a C7a H7a 107.2 . . ? H10a C10a H10b 109.5 . . ? H10a C10a H10c 109.5 . . ? H10b C10a H10c 109.5 . . ? C11a C10a H10a 109.5 . . ? C11a C10a H10b 109.5 . . ? C11a C10a H10c 109.5 . . ? N11a C11a C10a 121.5(2) . . ? N11a C11a C12a 111.3(2) . . ? C12a C11a C10a 127.2(2) . . ? C11a C12a C15a 127.6(2) . . ? C13a C12a C11a 105.6(2) . . ? C13a C12a C15a 126.8(2) . . ? N12a C13a C12a 106.8(2) . . ? N12a C13a C14a 123.3(2) . . ? C12a C13a C14a 129.9(2) . . ? C13a C14a H14a 109.5 . . ? C13a C14a H14b 109.5 . . ? C13a C14a H14c 109.5 . . ? H14a C14a H14b 109.5 . . ? H14a C14a H14c 109.5 . . ? H14b C14a H14c 109.5 . . ? C12a C15a H15a 109.5 . . ? C12a C15a H15b 109.5 . . ? C12a C15a H15c 109.5 . . ? H15a C15a H15b 109.5 . . ? H15a C15a H15c 109.5 . . ? H15b C15a H15c 109.5 . . ? H20a C20a H20b 109.5 . . ? H20a C20a H20c 109.5 . . ? H20b C20a H20c 109.5 . . ? C21a C20a H20a 109.5 . . ? C21a C20a H20b 109.5 . . ? C21a C20a H20c 109.5 . . ? N21a C21a C20a 124.5(2) . . ? N21a C21a C22a 110.8(2) . . ? C22a C21a C20a 124.6(2) . . ? C21a C22a C25a 125.8(3) . . ? C23a C22a C21a 106.2(2) . . ? C23a C22a C25a 128.0(2) . . ? N22a C23a C24a 123.0(2) . . ? C22a C23a N22a 106.6(2) . . ? C22a C23a C24a 130.3(2) . . ? C23a C24a H24a 109.5 . . ? C23a C24a H24b 109.5 . . ? C23a C24a H24c 109.5 . . ? H24a C24a H24b 109.5 . . ? H24a C24a H24c 109.5 . . ? H24b C24a H24c 109.5 . . ? C22a C25a H25a 109.5 . . ? C22a C25a H25b 109.5 . . ? C22a C25a H25c 109.5 . . ? H25a C25a H25b 109.5 . . ? H25a C25a H25c 109.5 . . ? H25b C25a H25c 109.5 . . ? H30a C30a H30b 109.5 . . ? H30a C30a H30c 109.5 . . ? H30b C30a H30c 109.5 . . ? C31a C30a H30a 109.5 . . ? C31a C30a H30b 109.5 . . ? C31a C30a H30c 109.5 . . ? N31a C31a C30a 122.3(2) . . ? N31a C31a C32a 111.3(2) . . ? C32a C31a C30a 126.3(2) . . ? C31a C32a C35a 127.1(2) . . ? C33a C32a C31a 105.6(2) . . ? C33a C32a C35a 127.3(2) . . ? N32a C33a C32a 106.6(2) . . ? N32a C33a C34a 123.8(2) . . ? C32a C33a C34a 129.7(2) . . ? C33a C34a H34a 109.5 . . ? C33a C34a H34b 109.5 . . ? C33a C34a H34c 109.5 . . ? H34a C34a H34b 109.5 . . ? H34a C34a H34c 109.5 . . ? H34b C34a H34c 109.5 . . ? C32a C35a H35a 109.5 . . ? C32a C35a H35b 109.5 . . ? C32a C35a H35c 109.5 . . ? H35a C35a H35b 109.5 . . ? H35a C35a H35c 109.5 . . ? H35b C35a H35c 109.5 . . ? H40a C40a H40b 109.5 . . ? H40a C40a H40c 109.5 . . ? H40b C40a H40c 109.5 . . ? C41a C40a H40a 109.5 . . ? C41a C40a H40b 109.5 . . ? C41a C40a H40c 109.5 . . ? N41a C41a C40a 124.4(2) . . ? N41a C41a C42a 111.2(2) . . ? C42a C41a C40a 124.3(2) . . ? C41a C42a C45a 127.3(2) . . ? C43a C42a C41a 105.7(2) . . ? C43a C42a C45a 127.0(2) . . ? N42a C43a C42a 106.7(2) . . ? N42a C43a C44a 125.0(2) . . ? C42a C43a C44a 128.3(2) . . ? C43a C44a H44a 109.5 . . ? C43a C44a H44b 109.5 . . ? C43a C44a H44c 109.5 . . ? H44a C44a H44b 109.5 . . ? H44a C44a H44c 109.5 . . ? H44b C44a H44c 109.5 . . ? C42a C45a H45a 109.5 . . ? C42a C45a H45b 109.5 . . ? C42a C45a H45c 109.5 . . ? H45a C45a H45b 109.5 . . ? H45a C45a H45c 109.5 . . ? H45b C45a H45c 109.5 . . ? 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 Fe1 N1 C2 C1 -10.3(3) . . . . ? Fe1 N1 C2 C3 172.52(18) . . . . ? Fe1 N1 C6 C5 -172.93(18) . . . . ? Fe1 N1 C6 C7 8.5(3) . . . . ? Fe1 N11 C11 C10 8.4(4) . . . . ? Fe1 N11 C11 C12 -173.36(19) . . . . ? Fe1 N21 C21 C20 32.4(4) . . . . ? Fe1 N21 C21 C22 -148.1(2) . . . . ? Fe1 N31 C31 C30 -11.7(4) . . . . ? Fe1 N31 C31 C32 165.97(18) . . . . ? Fe1 N41 C41 C40 -1.3(4) . . . . ? Fe1 N41 C41 C42 -179.19(17) . . . . ? Cl1 Fe1 N1 C2 -171(34) . . . . ? Cl1 Fe1 N1 C6 2(3) . . . . ? Cl1 Fe1 N11 N12 155.14(15) . . . . ? Cl1 Fe1 N11 C11 -31.6(3) . . . . ? Cl1 Fe1 N21 N22 -131.13(16) . . . . ? Cl1 Fe1 N21 C21 16.4(3) . . . . ? Cl1 Fe1 N31 N32 139.38(15) . . . . ? Cl1 Fe1 N31 C31 -24.8(2) . . . . ? Cl1 Fe1 N41 N42 -143.45(15) . . . . ? Cl1 Fe1 N41 C41 34.9(2) . . . . ? N1 Fe1 N11 N12 -25.47(16) . . . . ? N1 Fe1 N11 C11 147.8(3) . . . . ? N1 Fe1 N21 N22 49.66(17) . . . . ? N1 Fe1 N21 C21 -162.8(3) . . . . ? N1 Fe1 N31 N32 -40.03(16) . . . . ? N1 Fe1 N31 C31 155.8(3) . . . . ? N1 Fe1 N41 N42 35.73(15) . . . . ? N1 Fe1 N41 C41 -145.9(2) . . . . ? N1 C2 C1 N12 -57.4(3) . . . . ? N1 C2 C1 N22 68.3(3) . . . . ? N1 C2 C3 C4 0.6(4) . . . . ? N1 C6 C7 N32 -68.4(3) . . . . ? N1 C6 C7 N42 57.8(3) . . . . ? N11 Fe1 N1 C2 42.60(18) . . . . ? N11 Fe1 N1 C6 -144.69(18) . . . . ? N11 Fe1 N21 N22 -35.91(17) . . . . ? N11 Fe1 N21 C21 111.6(3) . . . . ? N11 Fe1 N31 N32 -38.0(4) . . . . ? N11 Fe1 N31 C31 157.9(3) . . . . ? N11 Fe1 N41 N42 118.33(16) . . . . ? N11 Fe1 N41 C41 -63.3(2) . . . . ? N11 N12 C1 N22 -49.8(3) . . . . ? N11 N12 C1 C2 77.2(3) . . . . ? N11 N12 C13 C12 -1.2(3) . . . . ? N11 N12 C13 C14 -179.5(2) . . . . ? N12 N11 C11 C10 -177.8(2) . . . . ? N12 N11 C11 C12 0.4(3) . . . . ? N12 C13 C12 C11 1.3(3) . . . . ? N12 C13 C12 C15 -178.7(2) . . . . ? N21 Fe1 N1 C2 -36.13(18) . . . . ? N21 Fe1 N1 C6 136.58(18) . . . . ? N21 Fe1 N11 N12 56.40(16) . . . . ? N21 Fe1 N11 C11 -130.3(3) . . . . ? N21 Fe1 N31 N32 -119.47(16) . . . . ? N21 Fe1 N31 C31 76.3(3) . . . . ? N21 Fe1 N41 N42 43.0(3) . . . . ? N21 Fe1 N41 C41 -138.7(3) . . . . ? N21 N22 C1 N12 76.2(3) . . . . ? N21 N22 C1 C2 -50.6(3) . . . . ? N21 N22 C23 C22 2.6(3) . . . . ? N21 N22 C23 C24 -174.2(3) . . . . ? N22 N21 C21 C20 -177.6(3) . . . . ? N22 N21 C21 C22 1.8(3) . . . . ? N22 C23 C22 C21 -1.3(3) . . . . ? N22 C23 C22 C25 178.1(3) . . . . ? N31 Fe1 N1 C2 -137.84(18) . . . . ? N31 Fe1 N1 C6 34.87(17) . . . . ? N31 Fe1 N11 N12 -27.5(4) . . . . ? N31 Fe1 N11 C11 145.7(3) . . . . ? N31 Fe1 N21 N22 131.78(17) . . . . ? N31 Fe1 N21 C21 -80.7(3) . . . . ? N31 Fe1 N41 N42 -49.52(15) . . . . ? N31 Fe1 N41 C41 128.8(2) . . . . ? N31 N32 C7 N42 -64.8(3) . . . . ? N31 N32 C7 C6 61.8(3) . . . . ? N31 N32 C33 C32 -1.5(3) . . . . ? N31 N32 C33 C34 178.3(2) . . . . ? N32 N31 C31 C30 -177.2(2) . . . . ? N32 N31 C31 C32 0.5(3) . . . . ? N32 C33 C32 C31 1.7(3) . . . . ? N32 C33 C32 C35 -179.6(3) . . . . ? N41 Fe1 N1 C2 141.75(19) . . . . ? N41 Fe1 N1 C6 -45.53(17) . . . . ? N41 Fe1 N11 N12 -107.01(16) . . . . ? N41 Fe1 N11 C11 66.3(3) . . . . ? N41 Fe1 N21 N22 42.4(4) . . . . ? N41 Fe1 N21 C21 -170.1(2) . . . . ? N41 Fe1 N31 N32 43.47(16) . . . . ? N41 Fe1 N31 C31 -120.7(3) . . . . ? N41 N42 C7 N32 57.6(3) . . . . ? N41 N42 C7 C6 -69.2(3) . . . . ? N41 N42 C43 C42 0.5(3) . . . . ? N41 N42 C43 C44 179.1(2) . . . . ? N42 N41 C41 C40 177.2(2) . . . . ? N42 N41 C41 C42 -0.7(3) . . . . ? N42 C43 C42 C41 -0.9(3) . . . . ? N42 C43 C42 C45 179.5(2) . . . . ? C1 N12 N11 Fe1 -22.9(3) . . . . ? C1 N12 N11 C11 161.6(2) . . . . ? C1 N12 C13 C12 -160.2(2) . . . . ? C1 N12 C13 C14 21.4(4) . . . . ? C1 N22 N21 Fe1 -16.0(3) . . . . ? C1 N22 N21 C21 -172.6(2) . . . . ? C1 N22 C23 C22 171.7(2) . . . . ? C1 N22 C23 C24 -5.1(4) . . . . ? C1 C2 C3 C4 -176.5(2) . . . . ? C2 N1 C6 C5 0.1(3) . . . . ? C2 N1 C6 C7 -178.5(2) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C2 C1 N12 119.9(2) . . . . ? C3 C2 C1 N22 -114.4(3) . . . . ? C3 C4 C5 C6 0.1(4) . . . . ? C4 C5 C6 N1 0.1(4) . . . . ? C4 C5 C6 C7 178.7(2) . . . . ? C5 C6 C7 N32 112.9(2) . . . . ? C5 C6 C7 N42 -120.8(2) . . . . ? C6 N1 C2 C1 176.8(2) . . . . ? C6 N1 C2 C3 -0.4(3) . . . . ? C7 N32 N31 Fe1 1.3(3) . . . . ? C7 N32 N31 C31 170.4(2) . . . . ? C7 N32 C33 C32 -170.4(2) . . . . ? C7 N32 C33 C34 9.4(4) . . . . ? C7 N42 N41 Fe1 10.0(3) . . . . ? C7 N42 N41 C41 -168.9(2) . . . . ? C7 N42 C43 C42 168.5(2) . . . . ? C7 N42 C43 C44 -12.9(4) . . . . ? C13 N12 N11 Fe1 175.94(16) . . . . ? C13 N12 N11 C11 0.5(3) . . . . ? C13 N12 C1 N22 108.1(3) . . . . ? C13 N12 C1 C2 -124.9(3) . . . . ? C13 C12 C11 N11 -1.1(3) . . . . ? C13 C12 C11 C10 177.0(3) . . . . ? C14 C13 C12 C11 179.6(3) . . . . ? C14 C13 C12 C15 -0.5(5) . . . . ? C15 C12 C11 N11 178.9(2) . . . . ? C15 C12 C11 C10 -3.0(4) . . . . ? C23 N22 N21 Fe1 153.83(17) . . . . ? C23 N22 N21 C21 -2.7(3) . . . . ? C23 N22 C1 N12 -92.1(3) . . . . ? C23 N22 C1 C2 141.2(3) . . . . ? C23 C22 C21 N21 -0.4(3) . . . . ? C23 C22 C21 C20 179.1(3) . . . . ? C24 C23 C22 C21 175.1(3) . . . . ? C24 C23 C22 C25 -5.4(5) . . . . ? C25 C22 C21 N21 -179.8(3) . . . . ? C25 C22 C21 C20 -0.3(5) . . . . ? C33 N32 N31 Fe1 -168.44(16) . . . . ? C33 N32 N31 C31 0.6(3) . . . . ? C33 N32 C7 N42 103.3(3) . . . . ? C33 N32 C7 C6 -130.1(2) . . . . ? C33 C32 C31 N31 -1.4(3) . . . . ? C33 C32 C31 C30 176.2(3) . . . . ? C34 C33 C32 C31 -178.1(3) . . . . ? C34 C33 C32 C35 0.6(5) . . . . ? C35 C32 C31 N31 179.9(3) . . . . ? C35 C32 C31 C30 -2.5(4) . . . . ? C43 N42 N41 Fe1 178.99(15) . . . . ? C43 N42 N41 C41 0.1(2) . . . . ? C43 N42 C7 N32 -109.5(3) . . . . ? C43 N42 C7 C6 123.8(2) . . . . ? C43 C42 C41 N41 1.0(3) . . . . ? C43 C42 C41 C40 -176.8(2) . . . . ? C44 C43 C42 C41 -179.4(3) . . . . ? C44 C43 C42 C45 1.0(5) . . . . ? C45 C42 C41 N41 -179.3(2) . . . . ? C45 C42 C41 C40 2.8(4) . . . . ? Fe1A N1A C2a C1a 3.7(3) . . . . ? Fe1A N1A C2a C3a -176.51(19) . . . . ? Fe1A N1A C6a C5a 176.74(18) . . . . ? Fe1A N1A C6a C7a -2.2(3) . . . . ? Fe1A N11a C11a C10a -20.4(4) . . . . ? Fe1A N11a C11a C12a 159.05(19) . . . . ? Fe1A N21a C21a C20a -5.5(4) . . . . ? Fe1A N21a C21a C22a 176.56(19) . . . . ? Fe1A N31a C31a C30a -16.0(4) . . . . ? Fe1A N31a C31a C32a 161.04(18) . . . . ? Fe1A N41a C41a C40a -10.4(4) . . . . ? Fe1A N41a C41a C42a 172.38(18) . . . . ? Cl1A Fe1A N1A C2a 53(2) . . . . ? Cl1A Fe1A N1A C6a -125(2) . . . . ? Cl1A Fe1A N11a N12a 133.23(16) . . . . ? Cl1A Fe1A N11a C11a -24.8(3) . . . . ? Cl1A Fe1A N21a N22a -152.18(15) . . . . ? Cl1A Fe1A N21a C21a 30.3(3) . . . . ? Cl1A Fe1A N31a N32a 132.23(15) . . . . ? Cl1A Fe1A N31a C31a -27.5(2) . . . . ? Cl1A Fe1A N41a N42a -156.02(15) . . . . ? Cl1A Fe1A N41a C41a 30.6(2) . . . . ? N1A Fe1A N11a N12a -47.09(17) . . . . ? N1A Fe1A N11a C11a 154.9(3) . . . . ? N1A Fe1A N21a N22a 26.25(16) . . . . ? N1A Fe1A N21a C21a -151.3(3) . . . . ? N1A Fe1A N31a N32a -47.48(15) . . . . ? N1A Fe1A N31a C31a 152.8(2) . . . . ? N1A Fe1A N41a N42a 25.54(15) . . . . ? N1A Fe1A N41a C41a -147.8(2) . . . . ? N1A C2a C1a N12a -66.1(3) . . . . ? N1A C2a C1a N22a 59.3(3) . . . . ? N1A C6a C5a C4a -0.2(4) . . . . ? N1A C6a C7a N32a -60.7(3) . . . . ? N1A C6a C7a N42a 64.7(3) . . . . ? N11a Fe1A N1A C2a 40.70(18) . . . . ? N11a Fe1A N1A C6a -136.52(18) . . . . ? N11a Fe1A N21a N22a -54.67(16) . . . . ? N11a Fe1A N21a C21a 127.8(3) . . . . ? N11a Fe1A N31a N32a -51.4(3) . . . . ? N11a Fe1A N31a C31a 148.9(2) . . . . ? N11a Fe1A N41a N42a 104.93(15) . . . . ? N11a Fe1A N41a C41a -68.5(3) . . . . ? N11a N12a C1a N22a -69.5(3) . . . . ? N11a N12a C1a C2a 57.3(3) . . . . ? N11a N12a C13a C12a -1.5(3) . . . . ? N11a N12a C13a C14a 179.1(3) . . . . ? N12a N11a C11a C10a 179.7(2) . . . . ? N12a N11a C11a C12a -0.8(3) . . . . ? N12a C13a C12a C11a 0.9(3) . . . . ? N12a C13a C12a C15a -179.4(3) . . . . ? N21a Fe1A N1A C2a -37.98(18) . . . . ? N21a Fe1A N1A C6a 144.80(18) . . . . ? N21a Fe1A N11a N12a 41.02(17) . . . . ? N21a Fe1A N11a C11a -117.0(3) . . . . ? N21a Fe1A N31a N32a -131.96(16) . . . . ? N21a Fe1A N31a C31a 68.3(2) . . . . ? N21a Fe1A N41a N42a 18.2(6) . . . . ? N21a Fe1A N41a C41a -155.2(5) . . . . ? N21a N22a C1a N12a 52.5(3) . . . . ? N21a N22a C1a C2a -73.4(3) . . . . ? N21a N22a C23a C22a 1.4(3) . . . . ? N21a N22a C23a C24a 179.6(2) . . . . ? N22a N21a C21a C20a 176.8(2) . . . . ? N22a N21a C21a C22a -1.1(3) . . . . ? N22a C23a C22a C21a -2.0(3) . . . . ? N22a C23a C22a C25a 178.3(3) . . . . ? N31a Fe1A N1A C2a -137.98(18) . . . . ? N31a Fe1A N1A C6a 44.80(17) . . . . ? N31a Fe1A N11a N12a -43.2(3) . . . . ? N31a Fe1A N11a C11a 158.8(2) . . . . ? N31a Fe1A N21a N22a 105.49(16) . . . . ? N31a Fe1A N21a C21a -72.0(3) . . . . ? N31a Fe1A N41a N42a -54.99(15) . . . . ? N31a Fe1A N41a C41a 131.6(3) . . . . ? N31a N32a C7a N42a -69.4(3) . . . . ? N31a N32a C7a C6a 56.6(3) . . . . ? N31a N32a C33a C32a -1.5(3) . . . . ? N31a N32a C33a C34a 178.1(2) . . . . ? N32a N31a C31a C30a -177.4(2) . . . . ? N32a N31a C31a C32a -0.4(3) . . . . ? N32a C33a C32a C31a 1.1(3) . . . . ? N32a C33a C32a C35a 178.8(2) . . . . ? N41a Fe1A N1A C2a 142.98(18) . . . . ? N41a Fe1A N1A C6a -34.25(17) . . . . ? N41a Fe1A N11a N12a -131.32(17) . . . . ? N41a Fe1A N11a C11a 70.6(3) . . . . ? N41a Fe1A N21a N22a 33.6(6) . . . . ? N41a Fe1A N21a C21a -144.0(5) . . . . ? N41a Fe1A N31a N32a 40.77(15) . . . . ? N41a Fe1A N31a C31a -119.0(2) . . . . ? N41a N42a C7a N32a 51.0(3) . . . . ? N41a N42a C7a C6a -75.2(3) . . . . ? N41a N42a C43a C42a 0.5(3) . . . . ? N41a N42a C43a C44a 179.3(2) . . . . ? N42a N41a C41a C40a 175.8(2) . . . . ? N42a N41a C41a C42a -1.5(3) . . . . ? N42a C43a C42a C41a -1.4(3) . . . . ? N42a C43a C42a C45a 179.6(2) . . . . ? C1a N12a N11a Fe1A 8.2(3) . . . . ? C1a N12a N11a C11a 172.6(2) . . . . ? C1a N12a C13a C12a -171.8(2) . . . . ? C1a N12a C13a C14a 8.9(4) . . . . ? C1a N22a N21a Fe1A 19.0(3) . . . . ? C1a N22a N21a C21a -162.7(2) . . . . ? C1a N22a C23a C22a 162.5(2) . . . . ? C1a N22a C23a C24a -19.2(4) . . . . ? C2a N1A C6a C5a -0.6(3) . . . . ? C2a N1A C6a C7a -179.5(2) . . . . ? C3a C2a C1a N12a 114.1(3) . . . . ? C3a C2a C1a N22a -120.5(2) . . . . ? C4a C3a C2a N1A -0.2(4) . . . . ? C4a C3a C2a C1a 179.6(2) . . . . ? C5a C4a C3a C2a -0.6(4) . . . . ? C5a C6a C7a N32a 120.3(2) . . . . ? C5a C6a C7a N42a -114.4(2) . . . . ? C6a N1A C2a C1a -179.0(2) . . . . ? C6a N1A C2a C3a 0.8(3) . . . . ? C6a C5a C4a C3a 0.8(4) . . . . ? C7a N32a N31a Fe1A 8.1(3) . . . . ? C7a N32a N31a C31a 173.7(2) . . . . ? C7a N32a C33a C32a -173.5(2) . . . . ? C7a N32a C33a C34a 6.1(4) . . . . ? C7a N42a N41a Fe1A 19.1(2) . . . . ? C7a N42a N41a C41a -165.33(19) . . . . ? C7a N42a C43a C42a 165.0(2) . . . . ? C7a N42a C43a C44a -16.2(4) . . . . ? C7a C6a C5a C4a 178.7(2) . . . . ? C13a N12a N11a Fe1A -162.95(17) . . . . ? C13a N12a N11a C11a 1.4(3) . . . . ? C13a N12a C1a N22a 100.0(3) . . . . ? C13a N12a C1a C2a -133.2(3) . . . . ? C13a C12a C11a N11a -0.1(3) . . . . ? C13a C12a C11a C10a 179.3(3) . . . . ? C14a C13a C12a C11a -179.7(3) . . . . ? C14a C13a C12a C15a -0.1(5) . . . . ? C15a C12a C11a N11a -179.7(3) . . . . ? C15a C12a C11a C10a -0.3(5) . . . . ? C23a N22a N21a Fe1A -178.49(15) . . . . ? C23a N22a N21a C21a -0.2(3) . . . . ? C23a N22a C1a N12a -107.3(3) . . . . ? C23a N22a C1a C2a 126.9(2) . . . . ? C23a C22a C21a N21a 2.0(3) . . . . ? C23a C22a C21a C20a -175.9(2) . . . . ? C24a C23a C22a C21a 179.9(3) . . . . ? C24a C23a C22a C25a 0.3(5) . . . . ? C25a C22a C21a N21a -178.3(2) . . . . ? C25a C22a C21a C20a 3.8(4) . . . . ? C33a N32a N31a Fe1A -164.43(15) . . . . ? C33a N32a N31a C31a 1.2(3) . . . . ? C33a N32a C7a N42a 102.0(3) . . . . ? C33a N32a C7a C6a -132.0(2) . . . . ? C33a C32a C31a N31a -0.5(3) . . . . ? C33a C32a C31a C30a 176.4(2) . . . . ? C34a C33a C32a C31a -178.4(3) . . . . ? C34a C33a C32a C35a -0.8(4) . . . . ? C35a C32a C31a N31a -178.1(2) . . . . ? C35a C32a C31a C30a -1.2(4) . . . . ? C43a N42a N41a Fe1A -174.96(15) . . . . ? C43a N42a N41a C41a 0.6(2) . . . . ? C43a N42a C7a N32a -112.5(3) . . . . ? C43a N42a C7a C6a 121.4(2) . . . . ? C43a C42a C41a N41a 1.8(3) . . . . ? C43a C42a C41a C40a -175.4(2) . . . . ? C44a C43a C42a C41a 179.9(2) . . . . ? C44a C43a C42a C45a 0.9(4) . . . . ? C45a C42a C41a N41a -179.1(2) . . . . ? C45a C42a C41a C40a 3.6(4) . . . . ? # start Validation Reply Form _vrf_PLAT214_GARD10M ; PROBLEM: Atom C2S (Anion/Solvent) ADP max/min Ratio 6.10 prola RESPONSE: Methanol molecules are strongly disordered within channels in the structure ; # end Validation Reply Form #===END # start Validation Reply Form _vrf_PLAT214_4x1pt75MeOH_100K_GARD10M ; PROBLEM: Atom C2S (Anion/Solvent) ADP max/min Ratio 6.10 prola RESPONSE: Methanol molecules are strongly disordered within channels in the structure ; # end Validation Reply Form data_1xCH2Cl2_270K_gard4ja _database_code_depnum_ccdc_archive 'CCDC 825572' #TrackingRef '- 1xCH2Cl2_270K _06022011.cif' _audit_creation_date 2011-05-11 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C19 H17 Cl Fe N9, C H2 Cl2, Cl' _chemical_formula_sum 'C20 H19 Cl4 Fe N9' _chemical_formula_weight 583.09 _chemical_melting_point ? 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' 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.5496(2) _cell_length_b 19.4285(3) _cell_length_c 12.0185(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.0400(10) _cell_angle_gamma 90.00 _cell_volume 2463.35(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8435 _cell_measurement_temperature 270(2) _cell_measurement_theta_max 66 _cell_measurement_theta_min 4 _exptl_absorpt_coefficient_mu 9.146 _exptl_absorpt_correction_T_max 0.2754 _exptl_absorpt_correction_T_min 0.1420 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Numerical (based on real shape/composition of the crystal) absorption correction (SHELXL-97) followed by SADABS procedure. Program for empirical absorption correction of area-detector data. University of Goetingen. Germany. Sheldrick, G. M. 1996 ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1184 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.19 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_unetI/netI 0.0237 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 20401 _diffrn_reflns_theta_full 67.10 _diffrn_reflns_theta_max 67.10 _diffrn_reflns_theta_min 2.27 _diffrn_ambient_temperature 270(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.963 _diffrn_measurement_device_type 'Bruker APEX2 CCD detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3815 _reflns_number_total 4234 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v7.23A (Bruker, 2005)' _computing_data_collection 'APEX2 v2.0-2 (Bruker, 2005)' _computing_data_reduction 'SADABS-2004/1 (Bruker, 2005)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 v.97-2 (Sheldrick, 1993-1997)' _computing_structure_solution 'XS/SHELXTL v6.12 (Bruker, 2001)' _refine_diff_density_max 0.562 _refine_diff_density_min -0.690 _refine_diff_density_rms 0.070 _refine_ls_extinction_coef 0.00046(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 4234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0444 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0815P)^2^+2.0903P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1224 _refine_ls_wR_factor_ref 0.1262 _refine_special_details ; The crystal represents pseudo-orthorhombic twin consisting of two monoclinic components with beta angle close to 90 deg. TWIN -1 0 0 0 -1 0 0 0 1 instruction was used during the refinement. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.49712(8) 0.12432(2) 0.30883(4) 0.02892(17) Uani 1 1 d . . . Cl1 Cl 0.49853(18) 0.13858(5) 0.49938(7) 0.0508(2) Uani 1 1 d . . . Cl1S Cl 0.4828(5) 0.28041(13) 0.0375(3) 0.1836(14) Uani 1 1 d . . . Cl2 Cl 0.99640(12) 0.11197(4) -0.03230(6) 0.0359(2) Uani 1 1 d . . . Cl2S Cl 0.5166(5) 0.40008(17) -0.0836(4) 0.243(2) Uani 1 1 d . . . N1 N 0.4949(5) 0.10934(13) 0.1180(2) 0.0308(6) Uani 1 1 d . . . N11 N 0.6527(3) 0.04881(19) 0.2875(4) 0.0367(9) Uani 1 1 d . . . N12 N 0.7387(3) 0.05934(19) 0.2033(4) 0.0382(9) Uani 1 1 d . . . N21 N 0.6457(3) 0.19783(19) 0.2595(4) 0.0366(9) Uani 1 1 d . . . N22 N 0.7299(4) 0.1805(2) 0.1803(4) 0.0407(10) Uani 1 1 d . . . N31 N 0.3430(4) 0.1942(2) 0.2636(4) 0.0387(10) Uani 1 1 d . . . N32 N 0.2570(3) 0.17460(19) 0.1850(4) 0.0379(9) Uani 1 1 d . . . N41 N 0.3475(4) 0.0455(2) 0.2927(4) 0.0378(10) Uani 1 1 d . . . N42 N 0.2577(4) 0.05259(18) 0.2134(4) 0.0350(9) Uani 1 1 d . . . C1 C 0.2662(4) 0.1080(2) 0.1315(4) 0.0391(13) Uani 1 1 d . . . H1 H 0.1940 0.1035 0.0807 0.047 Uiso 1 1 calc R . . C1S C 0.4173(15) 0.3310(9) -0.0614(9) 0.246(9) Uani 1 1 d . . . H H 0.3347 0.3470 -0.0373 0.295 Uiso 1 1 calc R . . Ha H 0.4066 0.3051 -0.1298 0.295 Uiso 1 1 calc R . . C2 C 0.3857(5) 0.1035(3) 0.0631(5) 0.0376(11) Uani 1 1 d . . . C3 C 0.3797(5) 0.0917(3) -0.0505(5) 0.0449(13) Uani 1 1 d . . . H3 H 0.3019 0.0874 -0.0863 0.054 Uiso 1 1 calc R . . C4 C 0.4914(7) 0.0866(2) -0.1093(3) 0.0529(11) Uani 1 1 d . . . H4 H 0.4901 0.0784 -0.1856 0.063 Uiso 1 1 calc R . . C5 C 0.6055(6) 0.0940(3) -0.0538(5) 0.0457(13) Uani 1 1 d . . . H5 H 0.6820 0.0916 -0.0920 0.055 Uiso 1 1 calc R . . C6 C 0.6031(5) 0.1049(2) 0.0598(4) 0.0324(10) Uani 1 1 d . . . C7 C 0.7250(5) 0.1141(2) 0.1254(5) 0.0370(12) Uani 1 1 d . . . H7 H 0.7960 0.1117 0.0730 0.044 Uiso 1 1 calc R . . C11 C 0.6958(6) -0.0061(3) 0.3403(6) 0.0505(15) Uani 1 1 d . . . H11 H 0.6574 -0.0253 0.4026 0.061 Uiso 1 1 calc R . . C12 C 0.8050(5) -0.0314(3) 0.2917(6) 0.0582(16) Uani 1 1 d . . . H12 H 0.8515 -0.0696 0.3142 0.070 Uiso 1 1 calc R . . C13 C 0.8299(5) 0.0098(3) 0.2064(6) 0.0493(14) Uani 1 1 d . . . H13 H 0.8977 0.0056 0.1574 0.059 Uiso 1 1 calc R . . C21 C 0.6740(5) 0.2617(3) 0.2861(5) 0.0507(14) Uani 1 1 d . . . H21 H 0.6314 0.2877 0.3392 0.061 Uiso 1 1 calc R . . C22 C 0.7767(6) 0.2848(3) 0.2238(6) 0.0635(18) Uani 1 1 d . . . H22 H 0.8157 0.3276 0.2289 0.076 Uiso 1 1 calc R . . C23 C 0.8088(5) 0.2330(3) 0.1545(5) 0.0495(14) Uani 1 1 d . . . H23 H 0.8718 0.2334 0.1004 0.059 Uiso 1 1 calc R . . C31 C 0.3096(5) 0.2587(3) 0.2911(6) 0.0473(13) Uani 1 1 d . . . H31 H 0.3511 0.2854 0.3441 0.057 Uiso 1 1 calc R . . C32 C 0.2048(6) 0.2806(3) 0.2299(7) 0.0627(18) Uani 1 1 d . . . H32 H 0.1650 0.3233 0.2330 0.075 Uiso 1 1 calc R . . C33 C 0.1727(5) 0.2250(3) 0.1636(6) 0.0564(16) Uani 1 1 d . . . H33 H 0.1054 0.2229 0.1136 0.068 Uiso 1 1 calc R . . C41 C 0.3169(6) -0.0114(3) 0.3473(5) 0.0444(13) Uani 1 1 d . . . H41 H 0.3623 -0.0292 0.4070 0.053 Uiso 1 1 calc R . . C42 C 0.2070(5) -0.0411(3) 0.3032(6) 0.0573(16) Uani 1 1 d . . . H42 H 0.1660 -0.0806 0.3276 0.069 Uiso 1 1 calc R . . C43 C 0.1727(5) 0.0009(3) 0.2158(7) 0.0570(19) Uani 1 1 d . . . H43 H 0.1043 -0.0052 0.1679 0.068 Uiso 1 1 calc R . . 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 0.0272(3) 0.0310(3) 0.0285(3) -0.00321(18) 0.0016(5) 0.0002(3) Cl1 0.0699(6) 0.0513(5) 0.0312(4) -0.0039(4) 0.0005(9) 0.0041(8) Cl1S 0.275(4) 0.1103(16) 0.165(2) 0.0711(16) 0.063(3) 0.002(2) Cl2 0.0288(4) 0.0407(4) 0.0382(4) -0.0018(3) 0.0020(7) -0.0027(5) Cl2S 0.326(5) 0.143(2) 0.259(4) 0.116(3) 0.045(5) -0.059(3) N1 0.0308(14) 0.0289(12) 0.0328(13) -0.0046(11) 0.002(2) -0.002(2) N11 0.038(2) 0.034(2) 0.037(2) -0.0001(19) -0.0004(19) 0.0050(16) N12 0.0271(18) 0.042(2) 0.046(2) -0.009(2) 0.0039(19) 0.0047(15) N21 0.036(2) 0.033(2) 0.040(2) -0.0109(19) 0.0093(18) -0.0052(16) N22 0.036(2) 0.040(2) 0.047(3) -0.008(2) 0.010(2) -0.0076(16) N31 0.0325(19) 0.039(2) 0.045(3) -0.006(2) -0.0030(18) 0.0027(16) N32 0.0306(18) 0.037(2) 0.046(2) -0.010(2) -0.0098(19) 0.0077(15) N41 0.036(2) 0.036(2) 0.041(3) -0.002(2) 0.0015(19) -0.0034(16) N42 0.0287(18) 0.0332(18) 0.043(2) -0.0023(18) 0.0027(18) -0.0056(15) C1 0.031(2) 0.042(2) 0.044(3) -0.010(2) -0.011(2) 0.0067(19) C1S 0.309(18) 0.34(2) 0.086(7) -0.001(10) -0.091(9) -0.170(16) C2 0.042(3) 0.031(2) 0.040(3) -0.004(2) -0.004(2) -0.002(2) C3 0.058(3) 0.036(3) 0.040(3) -0.005(2) -0.012(2) 0.001(2) C4 0.082(3) 0.049(2) 0.0283(17) -0.0088(15) -0.004(3) 0.008(3) C5 0.058(3) 0.045(3) 0.034(3) -0.004(2) 0.010(2) 0.002(2) C6 0.043(3) 0.026(2) 0.028(2) -0.003(2) 0.007(2) -0.0046(19) C7 0.033(2) 0.035(2) 0.042(3) -0.005(2) 0.015(2) 0.0006(18) C11 0.058(4) 0.042(3) 0.051(3) 0.002(3) -0.007(3) 0.002(2) C12 0.046(3) 0.055(3) 0.073(4) -0.003(3) -0.014(3) 0.022(2) C13 0.033(3) 0.044(3) 0.070(4) -0.012(3) -0.004(3) 0.010(2) C21 0.049(3) 0.049(3) 0.054(4) -0.012(3) 0.005(3) -0.011(2) C22 0.061(4) 0.044(3) 0.085(5) -0.009(3) 0.011(3) -0.026(3) C23 0.043(3) 0.049(3) 0.057(3) -0.002(3) 0.012(2) -0.019(2) C31 0.046(3) 0.038(3) 0.058(4) -0.018(3) -0.003(3) 0.005(2) C32 0.062(4) 0.047(3) 0.079(5) -0.017(3) -0.019(3) 0.025(3) C33 0.046(3) 0.050(3) 0.074(4) -0.008(3) -0.013(3) 0.015(2) C41 0.053(3) 0.038(3) 0.042(3) 0.000(2) 0.017(2) 0.000(2) C42 0.060(3) 0.033(2) 0.079(4) -0.002(3) 0.026(3) -0.013(2) C43 0.030(3) 0.057(4) 0.084(5) -0.031(4) 0.013(3) -0.012(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 Fe1 Cl1 2.3069(9) . ? Fe1 N1 2.311(3) . ? Fe1 N11 2.216(4) . ? Fe1 N21 2.202(4) . ? Fe1 N31 2.187(4) . ? Fe1 N41 2.208(4) . ? Cl1S C1S 1.690(15) . ? Cl2S C1S 1.724(13) . ? N1 C2 1.332(7) . ? N1 C6 1.342(6) . ? N11 N12 1.374(6) . ? N11 C11 1.322(6) . ? N12 C7 1.425(6) . ? N12 C13 1.362(6) . ? N21 N22 1.346(6) . ? N21 C21 1.315(6) . ? N22 C7 1.449(6) . ? N22 C23 1.352(6) . ? N31 N32 1.363(6) . ? N31 C31 1.343(6) . ? N32 C1 1.448(6) . ? N32 C33 1.348(6) . ? N41 N42 1.350(6) . ? N41 C41 1.326(6) . ? N42 C1 1.461(6) . ? N42 C43 1.347(6) . ? C1 H1 0.9800 . ? C1S H 0.9700 . ? C1S Ha 0.9700 . ? C2 C1 1.509(7) . ? C2 C3 1.386(8) . ? C3 H3 0.9300 . ? C3 C4 1.379(8) . ? C4 H4 0.9300 . ? C4 C5 1.383(8) . ? C5 H5 0.9300 . ? C5 C6 1.382(7) . ? C6 C7 1.518(7) . ? C7 H7 0.9800 . ? C11 H11 0.9300 . ? C11 C12 1.383(9) . ? C12 H12 0.9300 . ? C12 C13 1.328(10) . ? C13 H13 0.9300 . ? C21 H21 0.9300 . ? C21 C22 1.392(8) . ? C22 H22 0.9300 . ? C22 C23 1.349(9) . ? C23 H23 0.9300 . ? C31 H31 0.9300 . ? C31 C32 1.394(8) . ? C32 H32 0.9300 . ? C32 C33 1.384(9) . ? C33 H33 0.9300 . ? C41 H41 0.9300 . ? C41 C42 1.398(8) . ? C42 H42 0.9300 . ? C42 C43 1.378(10) . ? C43 H43 0.9300 . ? 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 Cl1 Fe1 N1 179.60(10) . . ? N11 Fe1 Cl1 100.97(12) . . ? N11 Fe1 N1 78.97(16) . . ? N21 Fe1 Cl1 100.69(12) . . ? N21 Fe1 N1 79.69(15) . . ? N21 Fe1 N11 82.59(15) . . ? N21 Fe1 N41 159.24(17) . . ? N31 Fe1 Cl1 100.17(13) . . ? N31 Fe1 N1 79.89(16) . . ? N31 Fe1 N11 158.86(16) . . ? N31 Fe1 N21 93.39(11) . . ? N31 Fe1 N41 82.99(15) . . ? N41 Fe1 Cl1 100.07(13) . . ? N41 Fe1 N1 79.55(15) . . ? N41 Fe1 N11 93.43(11) . . ? C2 N1 Fe1 120.7(3) . . ? C2 N1 C6 118.1(3) . . ? C6 N1 Fe1 121.2(3) . . ? N12 N11 Fe1 118.4(3) . . ? C11 N11 Fe1 137.1(4) . . ? C11 N11 N12 104.3(4) . . ? N11 N12 C7 121.9(4) . . ? C13 N12 N11 110.0(5) . . ? C13 N12 C7 128.1(5) . . ? N22 N21 Fe1 119.9(3) . . ? C21 N21 Fe1 135.1(4) . . ? C21 N21 N22 104.9(4) . . ? N21 N22 C7 121.4(4) . . ? N21 N22 C23 112.3(4) . . ? C23 N22 C7 126.1(5) . . ? N32 N31 Fe1 119.5(3) . . ? C31 N31 Fe1 135.5(4) . . ? C31 N31 N32 104.9(4) . . ? N31 N32 C1 120.9(3) . . ? C33 N32 N31 111.6(4) . . ? C33 N32 C1 127.5(4) . . ? N42 N41 Fe1 119.5(3) . . ? C41 N41 Fe1 135.2(4) . . ? C41 N41 N42 105.3(4) . . ? N41 N42 C1 120.5(4) . . ? C43 N42 N41 112.0(5) . . ? C43 N42 C1 127.2(5) . . ? N32 C1 N42 110.8(4) . . ? N32 C1 H1 107.8 . . ? N32 C1 C2 110.5(4) . . ? N42 C1 H1 107.8 . . ? N42 C1 C2 112.0(4) . . ? C2 C1 H1 107.8 . . ? Cl1S C1S Cl2S 108.3(7) . . ? Cl1S C1S H 110.0 . . ? Cl1S C1S Ha 110.0 . . ? Cl2S C1S H 110.0 . . ? Cl2S C1S Ha 110.0 . . ? H C1S Ha 108.4 . . ? N1 C2 C1 116.6(5) . . ? N1 C2 C3 122.8(5) . . ? C3 C2 C1 120.6(5) . . ? C2 C3 H3 120.7 . . ? C4 C3 C2 118.6(5) . . ? C4 C3 H3 120.7 . . ? C3 C4 H4 120.4 . . ? C3 C4 C5 119.3(3) . . ? C5 C4 H4 120.4 . . ? C4 C5 H5 120.8 . . ? C6 C5 C4 118.4(5) . . ? C6 C5 H5 120.8 . . ? N1 C6 C5 122.8(5) . . ? N1 C6 C7 116.2(4) . . ? C5 C6 C7 121.0(5) . . ? N12 C7 N22 111.2(5) . . ? N12 C7 C6 109.8(4) . . ? N12 C7 H7 108.0 . . ? N22 C7 C6 111.8(4) . . ? N22 C7 H7 108.0 . . ? C6 C7 H7 108.0 . . ? N11 C11 H11 124.1 . . ? N11 C11 C12 111.8(6) . . ? C12 C11 H11 124.1 . . ? C11 C12 H12 127.0 . . ? C13 C12 C11 106.1(5) . . ? C13 C12 H12 127.0 . . ? N12 C13 H13 126.1 . . ? C12 C13 N12 107.9(6) . . ? C12 C13 H13 126.1 . . ? N21 C21 H21 124.7 . . ? N21 C21 C22 110.5(5) . . ? C22 C21 H21 124.7 . . ? C21 C22 H22 126.7 . . ? C23 C22 C21 106.7(5) . . ? C23 C22 H22 126.7 . . ? N22 C23 H23 127.3 . . ? C22 C23 N22 105.5(5) . . ? C22 C23 H23 127.3 . . ? N31 C31 H31 124.4 . . ? N31 C31 C32 111.3(5) . . ? C32 C31 H31 124.4 . . ? C31 C32 H32 127.5 . . ? C33 C32 C31 105.1(5) . . ? C33 C32 H32 127.5 . . ? N32 C33 C32 107.2(5) . . ? N32 C33 H33 126.4 . . ? C32 C33 H33 126.4 . . ? N41 C41 H41 124.5 . . ? N41 C41 C42 111.0(6) . . ? C42 C41 H41 124.5 . . ? C41 C42 H42 127.4 . . ? C43 C42 C41 105.2(5) . . ? C43 C42 H42 127.4 . . ? N42 C43 C42 106.4(6) . . ? N42 C43 H43 126.8 . . ? C42 C43 H43 126.8 . . ? 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 Fe1 N1 C2 C1 0.7(5) . . . . ? Fe1 N1 C2 C3 -177.4(4) . . . . ? Fe1 N1 C6 C5 178.1(4) . . . . ? Fe1 N1 C6 C7 -3.2(5) . . . . ? Fe1 N11 N12 C7 -4.7(6) . . . . ? Fe1 N11 N12 C13 177.2(3) . . . . ? Fe1 N11 C11 C12 -175.9(4) . . . . ? Fe1 N21 N22 C7 0.5(6) . . . . ? Fe1 N21 N22 C23 175.6(4) . . . . ? Fe1 N21 C21 C22 -176.8(4) . . . . ? Fe1 N31 N32 C1 0.2(6) . . . . ? Fe1 N31 N32 C33 -177.0(4) . . . . ? Fe1 N31 C31 C32 175.6(5) . . . . ? Fe1 N41 N42 C1 6.2(5) . . . . ? Fe1 N41 N42 C43 -179.0(3) . . . . ? Fe1 N41 C41 C42 177.5(4) . . . . ? Cl1 Fe1 N1 C2 57(20) . . . . ? Cl1 Fe1 N1 C6 -122(20) . . . . ? Cl1 Fe1 N11 N12 -135.7(3) . . . . ? Cl1 Fe1 N11 C11 38.6(5) . . . . ? Cl1 Fe1 N21 N22 138.3(4) . . . . ? Cl1 Fe1 N21 C21 -45.4(6) . . . . ? Cl1 Fe1 N31 N32 -138.1(3) . . . . ? Cl1 Fe1 N31 C31 45.8(6) . . . . ? Cl1 Fe1 N41 N42 135.0(3) . . . . ? Cl1 Fe1 N41 C41 -42.2(5) . . . . ? N1 Fe1 N11 N12 44.7(3) . . . . ? N1 Fe1 N11 C11 -141.0(5) . . . . ? N1 Fe1 N21 N22 -41.6(4) . . . . ? N1 Fe1 N21 C21 134.7(6) . . . . ? N1 Fe1 N31 N32 41.5(4) . . . . ? N1 Fe1 N31 C31 -134.6(6) . . . . ? N1 Fe1 N41 N42 -45.1(3) . . . . ? N1 Fe1 N41 C41 137.7(5) . . . . ? N1 C2 C1 N32 61.8(6) . . . . ? N1 C2 C1 N42 -62.3(5) . . . . ? N1 C2 C3 C4 -0.8(8) . . . . ? N1 C6 C7 N12 64.9(5) . . . . ? N1 C6 C7 N22 -59.0(5) . . . . ? N11 Fe1 N1 C2 137.7(3) . . . . ? N11 Fe1 N1 C6 -41.0(3) . . . . ? N11 Fe1 N21 N22 38.5(4) . . . . ? N11 Fe1 N21 C21 -145.2(6) . . . . ? N11 Fe1 N31 N32 42.2(6) . . . . ? N11 Fe1 N31 C31 -133.9(6) . . . . ? N11 Fe1 N41 N42 -123.2(4) . . . . ? N11 Fe1 N41 C41 59.6(5) . . . . ? N11 N12 C7 N22 62.1(6) . . . . ? N11 N12 C7 C6 -62.1(6) . . . . ? N11 N12 C13 C12 -1.0(6) . . . . ? N11 C11 C12 C13 0.4(7) . . . . ? N12 N11 C11 C12 -1.0(6) . . . . ? N21 Fe1 N1 C2 -138.0(3) . . . . ? N21 Fe1 N1 C6 43.4(3) . . . . ? N21 Fe1 N11 N12 -36.2(3) . . . . ? N21 Fe1 N11 C11 138.1(5) . . . . ? N21 Fe1 N31 N32 120.4(4) . . . . ? N21 Fe1 N31 C31 -55.7(5) . . . . ? N21 Fe1 N41 N42 -45.1(6) . . . . ? N21 Fe1 N41 C41 137.7(5) . . . . ? N21 N22 C7 N12 -59.9(6) . . . . ? N21 N22 C7 C6 63.2(6) . . . . ? N21 N22 C23 C22 2.8(7) . . . . ? N21 C21 C22 C23 1.8(7) . . . . ? N22 N21 C21 C22 -0.1(7) . . . . ? N31 Fe1 N1 C2 -42.6(3) . . . . ? N31 Fe1 N1 C6 138.7(3) . . . . ? N31 Fe1 N11 N12 43.9(6) . . . . ? N31 Fe1 N11 C11 -141.7(5) . . . . ? N31 Fe1 N21 N22 -120.7(4) . . . . ? N31 Fe1 N21 C21 55.6(5) . . . . ? N31 Fe1 N41 N42 35.9(3) . . . . ? N31 Fe1 N41 C41 -141.3(5) . . . . ? N31 N32 C1 N42 60.0(6) . . . . ? N31 N32 C1 C2 -64.8(6) . . . . ? N31 N32 C33 C32 0.6(7) . . . . ? N31 C31 C32 C33 1.2(8) . . . . ? N32 N31 C31 C32 -0.8(7) . . . . ? N41 Fe1 N1 C2 42.0(3) . . . . ? N41 Fe1 N1 C6 -136.6(3) . . . . ? N41 Fe1 N11 N12 123.3(4) . . . . ? N41 Fe1 N11 C11 -62.3(5) . . . . ? N41 Fe1 N21 N22 -41.6(7) . . . . ? N41 Fe1 N21 C21 134.8(6) . . . . ? N41 Fe1 N31 N32 -39.1(4) . . . . ? N41 Fe1 N31 C31 144.8(6) . . . . ? N41 N42 C1 N32 -63.8(5) . . . . ? N41 N42 C1 C2 60.1(6) . . . . ? N41 N42 C43 C42 1.7(6) . . . . ? N41 C41 C42 C43 1.0(6) . . . . ? N42 N41 C41 C42 0.0(6) . . . . ? C1 N32 C33 C32 -176.4(6) . . . . ? C1 N42 C43 C42 176.0(5) . . . . ? C1 C2 C3 C4 -178.8(4) . . . . ? C2 N1 C6 C5 -0.6(5) . . . . ? C2 N1 C6 C7 178.1(4) . . . . ? C2 C3 C4 C5 -0.6(6) . . . . ? C3 C2 C1 N32 -120.0(5) . . . . ? C3 C2 C1 N42 115.9(5) . . . . ? C3 C4 C5 C6 1.2(6) . . . . ? C4 C5 C6 N1 -0.7(8) . . . . ? C4 C5 C6 C7 -179.3(4) . . . . ? C5 C6 C7 N12 -116.4(5) . . . . ? C5 C6 C7 N22 119.7(5) . . . . ? C6 N1 C2 C1 179.4(4) . . . . ? C6 N1 C2 C3 1.3(6) . . . . ? C7 N12 C13 C12 -178.9(5) . . . . ? C7 N22 C23 C22 177.7(5) . . . . ? C11 N11 N12 C7 179.3(4) . . . . ? C11 N11 N12 C13 1.2(6) . . . . ? C11 C12 C13 N12 0.3(7) . . . . ? C13 N12 C7 N22 -120.1(5) . . . . ? C13 N12 C7 C6 115.6(5) . . . . ? C21 N21 N22 C7 -176.8(5) . . . . ? C21 N21 N22 C23 -1.7(6) . . . . ? C21 C22 C23 N22 -2.7(7) . . . . ? C23 N22 C7 N12 125.7(5) . . . . ? C23 N22 C7 C6 -111.3(6) . . . . ? C31 N31 N32 C1 177.4(5) . . . . ? C31 N31 N32 C33 0.2(6) . . . . ? C31 C32 C33 N32 -1.0(8) . . . . ? C33 N32 C1 N42 -123.3(6) . . . . ? C33 N32 C1 C2 111.9(6) . . . . ? C41 N41 N42 C1 -175.9(4) . . . . ? C41 N41 N42 C43 -1.1(6) . . . . ? C41 C42 C43 N42 -1.6(6) . . . . ? C43 N42 C1 N32 122.2(5) . . . . ? C43 N42 C1 C2 -113.8(5) . . . . ?