#------------------------------------------------------------------------------ #$Date: 2020-08-18 05:02:47 +0300 (Tue, 18 Aug 2020) $ #$Revision: 255416 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705187.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7705187 loop_ _publ_author_name 'Liang, Qiuming' 'Lin, Jack H.' 'DeMuth, Joshua C.' 'Neidig, Michael L.' 'Song, Datong' _publ_section_title ; Syntheses and Characterizations of Iron Complexes of Bulky o-Phenylenediamide ligand ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT02087G _journal_year 2020 _chemical_formula_moiety 'C30 H38 Cl2 Fe N2, C4 H10 O' _chemical_formula_sum 'C34 H48 Cl2 Fe N2 O' _chemical_formula_weight 627.49 _space_group_crystal_system monoclinic _space_group_IT_number 11 _space_group_name_Hall '-P 2yb' _space_group_name_H-M_alt 'P 1 21/m 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2020-08-11 deposited with the CCDC. 2020-08-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.721(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.2114(4) _cell_length_b 17.4996(9) _cell_length_c 10.2150(6) _cell_measurement_reflns_used 12454 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.489 _cell_measurement_theta_min 2.429 _cell_volume 1707.30(15) _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker Kappa Apex II' _diffrn_measurement_method 'Phi and Omega Scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_unetI/netI 0.0655 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 12468 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.489 _diffrn_reflns_theta_min 2.429 _exptl_absorpt_coefficient_mu 0.625 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6760 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour 'dark green' _exptl_crystal_density_diffrn 1.221 _exptl_crystal_description block _exptl_crystal_F_000 668 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.597 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 213 _refine_ls_number_reflns 4044 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0704 _refine_ls_R_factor_gt 0.0437 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.9936P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0927 _refine_ls_wR_factor_ref 0.1038 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2945 _reflns_number_total 4044 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02087g2.cif _cod_data_source_block wl311 _cod_original_sg_symbol_H-M 'P 21/m' _cod_database_code 7705187 _shelx_shelxl_version_number 2016/6 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; TITL wl311 in P2(1)/m wl311.res created by SHELXL-2016/6 at 02:18:03 on 08-Aug-2020 CELL 0.71073 10.2114 17.4996 10.2150 90.000 110.721 90.000 ZERR 2.00 0.0004 0.0009 0.0006 0.000 0.002 0.000 LATT 1 SYMM -x, y+1/2, -z SFAC C H N CL FE O UNIT 68 96 4 4 2 2 TEMP -123.000 ACTA L.S. 8 FMAP 2 PLAN -5 0 0.00 HTAB EADP O1 O1A EADP C16 C16A EADP C17 C17A EADP C18 C18A EADP C19 C19A OMIT 0 0 1 BOND $H CONF WGHT 0.034800 0.993600 FVAR 0.22674 0.12776 FE1 5 0.370804 0.250000 0.457343 10.50000 0.01425 0.01729 = 0.02496 0.00000 0.01117 0.00000 CL1 4 0.327045 0.250000 0.231304 10.50000 0.03238 0.04966 = 0.02728 0.00000 0.01663 0.00000 N1 3 0.255117 0.323369 0.514028 11.00000 0.01563 0.01241 = 0.02016 0.00253 0.00868 0.00072 C1 1 0.145299 0.291841 0.533761 11.00000 0.01545 0.01440 = 0.01596 -0.00039 0.00714 -0.00052 CL2 4 0.593317 0.250000 0.590919 10.50000 0.01405 0.03418 = 0.03677 0.00000 0.01005 0.00000 C2 1 0.034702 0.331079 0.558551 11.00000 0.02078 0.01491 = 0.02316 0.00135 0.01042 0.00369 AFIX 43 H2 2 0.033289 0.385353 0.559532 11.00000 -1.20000 AFIX 0 C3 1 -0.068952 0.290847 0.580832 11.00000 0.01732 0.02354 = 0.02654 -0.00025 0.01225 0.00283 AFIX 43 H3 2 -0.143021 0.317463 0.596754 11.00000 -1.20000 AFIX 0 C4 1 0.281020 0.404750 0.533416 11.00000 0.01711 0.01250 = 0.02732 0.00266 0.01227 0.00070 C5 1 0.368193 0.429403 0.666428 11.00000 0.02166 0.01636 = 0.02904 -0.00106 0.01108 -0.00037 C6 1 0.402475 0.506870 0.681694 11.00000 0.03459 0.01997 = 0.03902 -0.00659 0.01146 -0.00392 AFIX 43 H6 2 0.459529 0.525760 0.770838 11.00000 -1.20000 AFIX 0 C7 1 0.355253 0.556557 0.570075 11.00000 0.04889 0.01438 = 0.05722 -0.00159 0.02416 -0.00503 AFIX 43 H7 2 0.382263 0.608786 0.581990 11.00000 -1.20000 AFIX 0 C8 1 0.269021 0.530492 0.441452 11.00000 0.04531 0.01713 = 0.04481 0.01181 0.02306 0.00829 AFIX 43 H8 2 0.236665 0.565417 0.365555 11.00000 -1.20000 AFIX 0 C9 1 0.227775 0.454135 0.419426 11.00000 0.02635 0.02120 = 0.02916 0.00485 0.01515 0.00507 C10 1 0.422213 0.375924 0.790941 11.00000 0.03162 0.02193 = 0.02476 -0.00185 0.00614 0.00010 AFIX 13 H10 2 0.409385 0.322514 0.753728 11.00000 -1.20000 AFIX 0 C11 1 0.577632 0.386719 0.873952 11.00000 0.03393 0.04526 = 0.03920 -0.00159 0.00026 0.00222 AFIX 137 H11A 2 0.630131 0.385036 0.810141 11.00000 -1.50000 H11B 2 0.610328 0.345793 0.943428 11.00000 -1.50000 H11C 2 0.592410 0.436273 0.921682 11.00000 -1.50000 AFIX 0 C12 1 0.336736 0.383686 0.886097 11.00000 0.04956 0.05156 = 0.03402 0.00600 0.01659 0.00177 AFIX 137 H12A 2 0.343936 0.436159 0.921475 11.00000 -1.50000 H12B 2 0.372897 0.348200 0.964957 11.00000 -1.50000 H12C 2 0.238445 0.371687 0.833011 11.00000 -1.50000 AFIX 0 C13 1 0.126753 0.428406 0.277698 11.00000 0.03384 0.02868 = 0.02678 0.01073 0.00810 0.00687 AFIX 13 H13 2 0.114843 0.371828 0.281540 11.00000 -1.20000 AFIX 0 C14 1 0.180933 0.445400 0.159320 11.00000 0.05440 0.05258 = 0.03160 0.00909 0.01665 0.00551 AFIX 137 H14A 2 0.117059 0.423239 0.071951 11.00000 -1.50000 H14B 2 0.274316 0.423047 0.181657 11.00000 -1.50000 H14C 2 0.186208 0.500823 0.148354 11.00000 -1.50000 AFIX 0 C15 1 -0.017544 0.465675 0.246381 11.00000 0.03931 0.06955 = 0.04018 0.01363 0.00831 0.01782 AFIX 137 H15A 2 -0.009314 0.521136 0.238464 11.00000 -1.50000 H15B 2 -0.051852 0.454213 0.322504 11.00000 -1.50000 H15C 2 -0.083412 0.445422 0.158219 11.00000 -1.50000 AFIX 0 PART 1 O1 6 0.815863 0.250000 0.077123 10.25000 0.02658 0.03759 = 0.02059 0.00000 0.00534 0.00000 C16 1 0.819322 0.250000 0.212761 10.25000 0.02698 0.05629 = 0.01279 0.00000 -0.00011 0.00000 AFIX 3 H16A 2 0.870291 0.294140 0.259821 10.25000 -1.20000 H16B 2 0.870291 0.205860 0.259821 10.25000 -1.20000 AFIX 0 C17 1 0.674619 0.250000 0.222864 10.25000 0.02555 0.11033 = 0.03118 0.00000 0.00866 0.00000 AFIX 3 H17A 2 0.688891 0.250000 0.320944 10.25000 -1.50000 H17B 2 0.622949 0.294790 0.179874 10.25000 -1.50000 H17C 2 0.622949 0.205210 0.179874 10.25000 -1.50000 AFIX 0 C18 1 0.942984 0.250000 0.054060 10.25000 0.00759 0.09062 = 0.03174 0.00000 0.00136 0.00000 AFIX 3 H18A 2 0.995584 0.205780 0.098650 10.25000 -1.20000 H18B 2 0.995584 0.294220 0.098650 10.25000 -1.20000 AFIX 0 C19 1 0.933465 0.250000 -0.087129 10.25000 0.03524 0.09898 = 0.02720 0.00000 0.00908 0.00000 AFIX 3 H19A 2 1.025484 0.250000 -0.092399 10.25000 -1.50000 H19B 2 0.883734 0.205210 -0.132679 10.25000 -1.50000 H19C 2 0.883734 0.294790 -0.132679 10.25000 -1.50000 AFIX 0 PART 2 O1A 6 0.819309 0.228676 0.080416 10.25000 0.02658 0.03759 = 0.02059 0.00000 0.00534 0.00000 C16A 1 0.797906 0.228145 0.194772 10.25000 0.02698 0.05629 = 0.01279 0.00000 -0.00011 0.00000 AFIX 3 H16C 2 0.838027 0.275566 0.237672 10.25000 -1.20000 H16D 2 0.859687 0.188576 0.246652 10.25000 -1.20000 AFIX 0 C17A 1 0.698383 0.221975 0.233673 10.25000 0.02555 0.11033 = 0.03118 0.00000 0.00866 0.00000 AFIX 3 H17D 2 0.718483 0.223945 0.332804 10.25000 -1.50000 H17E 2 0.634643 0.262335 0.188773 10.25000 -1.50000 H17F 2 0.656753 0.173575 0.197943 10.25000 -1.50000 AFIX 0 C18A 1 0.916865 0.222196 0.042497 10.25000 0.00759 0.09062 = 0.03174 0.00000 0.00136 0.00000 AFIX 3 H18C 2 0.976324 0.183336 0.099707 10.25000 -1.20000 H18D 2 0.960585 0.269786 0.080627 10.25000 -1.20000 AFIX 0 C19A 1 0.945327 0.221540 -0.072744 10.25000 0.03524 0.09898 = 0.02720 0.00000 0.00908 0.00000 AFIX 3 H19D 2 1.043626 0.225910 -0.056114 10.25000 -1.50000 H19E 2 0.911927 0.172920 -0.114864 10.25000 -1.50000 H19F 2 0.895757 0.261700 -0.134454 10.25000 -1.50000 PART 0 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM wl311 in P2(1)/m REM R1 = 0.0437 for 2945 Fo > 4sig(Fo) and 0.0704 for all 4044 data REM 213 parameters refined using 0 restraints END WGHT 0.0348 0.9937 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.597, deepest hole -0.467, 1-sigma level 0.066 Q1 1 0.9011 0.2500 0.2852 10.50000 0.05 0.60 Q2 1 1.0274 0.2500 0.1436 10.50000 0.05 0.46 Q3 1 0.1362 0.2500 0.5186 10.50000 0.05 0.46 Q4 1 0.5757 0.2500 0.1383 10.50000 0.05 0.43 Q5 1 0.2603 0.2500 0.2836 10.50000 0.05 0.32 ; _shelx_res_checksum 81767 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Fe1 Fe 0.37080(4) 0.250000 0.45734(5) 0.01769(13) Uani 1 2 d S T P . . Cl1 Cl 0.32705(9) 0.250000 0.23130(10) 0.0348(2) Uani 1 2 d S T P . . N1 N 0.25512(17) 0.32337(10) 0.51403(19) 0.0154(4) Uani 1 1 d . . . . . C1 C 0.1453(2) 0.29184(11) 0.5338(2) 0.0148(4) Uani 1 1 d . . . . . Cl2 Cl 0.59332(8) 0.250000 0.59092(10) 0.0280(2) Uani 1 2 d S T P . . C2 C 0.0347(2) 0.33108(12) 0.5586(2) 0.0189(5) Uani 1 1 d . . . . . H2 H 0.033289 0.385353 0.559532 0.023 Uiso 1 1 calc R U . . . C3 C -0.0690(2) 0.29085(12) 0.5808(2) 0.0213(5) Uani 1 1 d . . . . . H3 H -0.143021 0.317463 0.596754 0.026 Uiso 1 1 calc R U . . . C4 C 0.2810(2) 0.40475(12) 0.5334(2) 0.0178(5) Uani 1 1 d . . . . . C5 C 0.3682(2) 0.42940(12) 0.6664(3) 0.0218(5) Uani 1 1 d . . . . . C6 C 0.4025(3) 0.50687(13) 0.6817(3) 0.0316(6) Uani 1 1 d . . . . . H6 H 0.459529 0.525760 0.770838 0.038 Uiso 1 1 calc R U . . . C7 C 0.3553(3) 0.55656(14) 0.5701(3) 0.0387(7) Uani 1 1 d . . . . . H7 H 0.382263 0.608786 0.581990 0.046 Uiso 1 1 calc R U . . . C8 C 0.2690(3) 0.53049(14) 0.4415(3) 0.0338(6) Uani 1 1 d . . . . . H8 H 0.236665 0.565417 0.365555 0.041 Uiso 1 1 calc R U . . . C9 C 0.2278(2) 0.45413(13) 0.4194(3) 0.0241(5) Uani 1 1 d . . . . . C10 C 0.4222(2) 0.37592(14) 0.7909(3) 0.0271(5) Uani 1 1 d . . . . . H10 H 0.409385 0.322514 0.753728 0.033 Uiso 1 1 calc R U . . . C11 C 0.5776(3) 0.38672(17) 0.8740(3) 0.0429(7) Uani 1 1 d . . . . . H11A H 0.630131 0.385036 0.810141 0.064 Uiso 1 1 calc R U . . . H11B H 0.610328 0.345793 0.943428 0.064 Uiso 1 1 calc R U . . . H11C H 0.592410 0.436273 0.921682 0.064 Uiso 1 1 calc R U . . . C12 C 0.3367(3) 0.38369(18) 0.8861(3) 0.0446(7) Uani 1 1 d . . . . . H12A H 0.343936 0.436159 0.921475 0.067 Uiso 1 1 calc R U . . . H12B H 0.372897 0.348200 0.964957 0.067 Uiso 1 1 calc R U . . . H12C H 0.238445 0.371687 0.833011 0.067 Uiso 1 1 calc R U . . . C13 C 0.1268(3) 0.42841(14) 0.2777(3) 0.0305(6) Uani 1 1 d . . . . . H13 H 0.114843 0.371828 0.281540 0.037 Uiso 1 1 calc R U . . . C14 C 0.1809(3) 0.44540(18) 0.1593(3) 0.0458(8) Uani 1 1 d . . . . . H14A H 0.117059 0.423239 0.071951 0.069 Uiso 1 1 calc R U . . . H14B H 0.274316 0.423047 0.181657 0.069 Uiso 1 1 calc R U . . . H14C H 0.186208 0.500823 0.148354 0.069 Uiso 1 1 calc R U . . . C15 C -0.0175(3) 0.46567(19) 0.2464(3) 0.0512(8) Uani 1 1 d . . . . . H15A H -0.009314 0.521136 0.238464 0.077 Uiso 1 1 calc R U . . . H15B H -0.051852 0.454213 0.322504 0.077 Uiso 1 1 calc R U . . . H15C H -0.083412 0.445422 0.158219 0.077 Uiso 1 1 calc R U . . . O1 O 0.8159(13) 0.250000 0.0771(13) 0.029(6) Uani 0.5 2 d S T P A 1 C16 C 0.819(3) 0.250000 0.213(3) 0.034(4) Uani 0.5 2 d S T P A 1 H16A H 0.870291 0.294140 0.259821 0.041 Uiso 0.25 1 d R U P A 1 H16B H 0.870291 0.205860 0.259821 0.041 Uiso 0.25 1 d R U P A 1 C17 C 0.675(4) 0.250000 0.223(3) 0.056(7) Uani 0.5 2 d S T P A 1 H17A H 0.688891 0.250000 0.320944 0.084 Uiso 0.5 2 d R U P A 1 H17B H 0.622949 0.294790 0.179874 0.084 Uiso 0.25 1 d R U P A 1 H17C H 0.622949 0.205210 0.179874 0.084 Uiso 0.25 1 d R U P A 1 C18 C 0.943(3) 0.250000 0.054(2) 0.045(5) Uani 0.5 2 d S T P A 1 H18A H 0.995584 0.205780 0.098650 0.054 Uiso 0.25 1 d R U P A 1 H18B H 0.995584 0.294220 0.098650 0.054 Uiso 0.25 1 d R U P A 1 C19 C 0.933(3) 0.250000 -0.087(3) 0.054(10) Uani 0.5 2 d S T P A 1 H19A H 1.025484 0.250000 -0.092399 0.082 Uiso 0.5 2 d R U P A 1 H19B H 0.883734 0.205210 -0.132679 0.082 Uiso 0.25 1 d R U P A 1 H19C H 0.883734 0.294790 -0.132679 0.082 Uiso 0.25 1 d R U P A 1 O1A O 0.8193(16) 0.229(2) 0.0804(16) 0.029(6) Uani 0.25 1 d . . P B 2 C16A C 0.798(3) 0.228(2) 0.195(3) 0.034(4) Uani 0.25 1 d . . P B 2 H16C H 0.838027 0.275566 0.237672 0.041 Uiso 0.25 1 d R U P B 2 H16D H 0.859687 0.188576 0.246652 0.041 Uiso 0.25 1 d R U P B 2 C17A C 0.698(4) 0.222(3) 0.234(3) 0.056(7) Uani 0.25 1 d . . P B 2 H17D H 0.718483 0.223945 0.332804 0.084 Uiso 0.25 1 d R U P B 2 H17E H 0.634643 0.262335 0.188773 0.084 Uiso 0.25 1 d R U P B 2 H17F H 0.656753 0.173575 0.197943 0.084 Uiso 0.25 1 d R U P B 2 C18A C 0.917(3) 0.222(2) 0.042(2) 0.045(5) Uani 0.25 1 d . . P B 2 H18C H 0.976324 0.183336 0.099707 0.054 Uiso 0.25 1 d R U P B 2 H18D H 0.960585 0.269786 0.080627 0.054 Uiso 0.25 1 d R U P B 2 C19A C 0.945(3) 0.222(3) -0.073(3) 0.054(10) Uani 0.25 1 d . . P B 2 H19D H 1.043626 0.225910 -0.056114 0.082 Uiso 0.25 1 d R U P B 2 H19E H 0.911927 0.172920 -0.114864 0.082 Uiso 0.25 1 d R U P B 2 H19F H 0.895757 0.261700 -0.134454 0.082 Uiso 0.25 1 d R U P B 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 0.0143(2) 0.0173(2) 0.0250(3) 0.000 0.01117(19) 0.000 Cl1 0.0324(5) 0.0497(6) 0.0273(5) 0.000 0.0166(4) 0.000 N1 0.0156(9) 0.0124(8) 0.0202(10) 0.0025(7) 0.0087(8) 0.0007(7) C1 0.0155(9) 0.0144(10) 0.0160(11) -0.0004(9) 0.0071(8) -0.0005(8) Cl2 0.0141(4) 0.0342(5) 0.0368(5) 0.000 0.0100(3) 0.000 C2 0.0208(11) 0.0149(10) 0.0232(13) 0.0013(9) 0.0104(9) 0.0037(9) C3 0.0173(10) 0.0235(12) 0.0265(13) -0.0002(10) 0.0122(9) 0.0028(9) C4 0.0171(10) 0.0125(10) 0.0273(13) 0.0027(9) 0.0123(9) 0.0007(9) C5 0.0217(11) 0.0164(11) 0.0290(14) -0.0011(10) 0.0111(10) -0.0004(9) C6 0.0346(14) 0.0200(12) 0.0390(17) -0.0066(11) 0.0115(12) -0.0039(11) C7 0.0489(17) 0.0144(12) 0.057(2) -0.0016(12) 0.0242(15) -0.0050(12) C8 0.0453(16) 0.0171(12) 0.0448(18) 0.0118(12) 0.0231(14) 0.0083(12) C9 0.0263(12) 0.0212(12) 0.0292(14) 0.0048(10) 0.0151(11) 0.0051(10) C10 0.0316(13) 0.0219(12) 0.0248(14) -0.0019(10) 0.0061(11) 0.0001(11) C11 0.0339(15) 0.0453(17) 0.0392(18) -0.0016(14) 0.0003(12) 0.0022(13) C12 0.0496(17) 0.0516(18) 0.0340(18) 0.0060(14) 0.0166(14) 0.0018(15) C13 0.0338(13) 0.0287(13) 0.0268(15) 0.0107(11) 0.0081(11) 0.0069(11) C14 0.0544(18) 0.0526(19) 0.0316(17) 0.0091(14) 0.0166(14) 0.0055(15) C15 0.0393(16) 0.070(2) 0.0402(19) 0.0136(16) 0.0083(14) 0.0178(16) O1 0.0266(15) 0.038(18) 0.0206(17) 0.000 0.0053(12) 0.000 C16 0.027(8) 0.056(18) 0.013(6) 0.000 0.000(6) 0.000 C17 0.026(9) 0.11(3) 0.031(4) 0.000 0.009(5) 0.000 C18 0.008(8) 0.09(2) 0.032(4) 0.000 0.001(5) 0.000 C19 0.035(4) 0.10(3) 0.027(5) 0.000 0.009(4) 0.000 O1A 0.0266(15) 0.038(18) 0.0206(17) 0.000 0.0053(12) 0.000 C16A 0.027(8) 0.056(18) 0.013(6) 0.000 0.000(6) 0.000 C17A 0.026(9) 0.11(3) 0.031(4) 0.000 0.009(5) 0.000 C18A 0.008(8) 0.09(2) 0.032(4) 0.000 0.001(5) 0.000 C19A 0.035(4) 0.10(3) 0.027(5) 0.000 0.009(4) 0.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Fe1 N1 81.57(10) . 4_565 ? N1 Fe1 Cl1 113.00(6) . . ? N1 Fe1 Cl1 113.00(6) 4_565 . ? N1 Fe1 Cl2 114.47(6) . . ? N1 Fe1 Cl2 114.47(6) 4_565 . ? Cl1 Fe1 Cl2 115.77(4) . . ? C1 N1 C4 120.71(17) . . ? C1 N1 Fe1 113.66(13) . . ? C4 N1 Fe1 125.63(13) . . ? N1 C1 C2 126.47(19) . . ? N1 C1 C1 114.55(11) . 4_565 ? C2 C1 C1 118.94(12) . 4_565 ? C3 C2 C1 119.8(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C3 121.28(13) . 4_565 ? C2 C3 H3 119.4 . . ? C3 C3 H3 119.4 4_565 . ? C9 C4 C5 122.9(2) . . ? C9 C4 N1 119.7(2) . . ? C5 C4 N1 117.20(19) . . ? C6 C5 C4 117.1(2) . . ? C6 C5 C10 120.2(2) . . ? C4 C5 C10 122.69(19) . . ? C7 C6 C5 121.3(2) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C8 C7 C6 120.0(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 121.8(2) . . ? C7 C8 H8 119.1 . . ? C9 C8 H8 119.1 . . ? C8 C9 C4 116.9(2) . . ? C8 C9 C13 120.1(2) . . ? C4 C9 C13 123.0(2) . . ? C5 C10 C11 112.8(2) . . ? C5 C10 C12 111.0(2) . . ? C11 C10 C12 110.6(2) . . ? C5 C10 H10 107.3 . . ? C11 C10 H10 107.3 . . ? C12 C10 H10 107.3 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 C14 112.5(2) . . ? C9 C13 C15 110.5(2) . . ? C14 C13 C15 110.0(2) . . ? C9 C13 H13 107.9 . . ? C14 C13 H13 107.9 . . ? C15 C13 H13 107.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C16 O1 C18 118.4(19) . . ? O1 C16 C17 113(3) . . ? O1 C16 H16A 108.7 . . ? C17 C16 H16A 109.5 . . ? O1 C16 H16B 108.7 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 107.1 . . ? C16 C17 H17A 106.2 . . ? C16 C17 H17B 111.1 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 111.1 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C17 H17E 123(6) . 4_565 ? H17A C17 H17E 122.0 . 4_565 ? H17B C17 H17E 81.2 . 4_565 ? H17C C17 H17E 28.2 . 4_565 ? O1 C18 C19 116(2) . . ? O1 C18 H18A 108.5 . . ? C19 C18 H18A 108.0 . . ? O1 C18 H18B 108.5 . . ? C19 C18 H18B 108.0 . . ? H18A C18 H18B 107.4 . . ? C18 C19 H19A 110.0 . . ? C18 C19 H19B 109.2 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.2 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C19 H19F 133(5) . 4_565 ? H19A C19 H19F 110.6 . 4_565 ? H19B C19 H19F 33.9 . 4_565 ? H19C C19 H19F 77.8 . 4_565 ? O1A O1A C18A 95(3) 4_565 . ? O1A O1A C16A 90(3) 4_565 . ? C18A O1A C16A 137(3) . . ? C16A C16A C17A 95(3) 4_565 . ? C16A C16A O1A 90(3) 4_565 . ? C17A C16A O1A 138(3) . . ? C16A C16A H16C 30.2 4_565 . ? C17A C16A H16C 101.4 . . ? O1A C16A H16C 103.3 . . ? O1A C16A H16C 76.1 4_565 . ? C17A C16A H16C 66.1 4_565 . ? C16A C16A H16D 136.2 4_565 . ? C17A C16A H16D 102.5 . . ? O1A C16A H16D 102.8 . . ? O1A C16A H16D 123.8 4_565 . ? C17A C16A H16D 130.5 4_565 . ? H16C C16A H16D 106.3 . . ? H16A C16A H16B 81.3 4_565 4_565 ? C17A C17A C16A 85(3) 4_565 . ? C17A C17A H17D 87.9 4_565 . ? C16A C17A H17D 116.7 . . ? C16A C17A H17D 110.3 4_565 . ? C17A C17A H17E 42.6 4_565 . ? C16A C17A H17E 106.3 . . ? C16A C17A H17E 81.6 4_565 . ? H17D C17A H17E 109.5 . . ? C17A C17A H17F 151.9 4_565 . ? C16A C17A H17F 105.2 . . ? C16A C17A H17F 131.7 4_565 . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? H17B C17A H17C 79.6 4_565 4_565 ? H17B C17A H17E 43.7 4_565 4_565 ? H17C C17A H17E 35.9 4_565 4_565 ? C18A C18A O1A 85(3) 4_565 . ? C18A C18A C19A 91(3) 4_565 . ? O1A C18A C19A 140(3) . . ? C18A C18A H18C 135.1 4_565 . ? O1A C18A H18C 106.9 . . ? C19A C18A H18C 104.3 . . ? O1A C18A H18C 126.6 4_565 . ? C19A C18A H18C 128.9 4_565 . ? C18A C18A H18D 29.8 4_565 . ? O1A C18A H18D 96.2 . . ? C19A C18A H18D 98.8 . . ? O1A C18A H18D 69.3 4_565 . ? C19A C18A H18D 66.1 4_565 . ? H18C C18A H18D 105.3 . . ? H18A C18A H18B 77.0 4_565 4_565 ? C19A C19A C18A 89(3) 4_565 . ? C19A C19A H19D 85.4 4_565 . ? C18A C19A H19D 113.0 . . ? C18A C19A H19D 105.4 4_565 . ? C19A C19A H19E 152.4 4_565 . ? C18A C19A H19E 104.7 . . ? C18A C19A H19E 136.9 4_565 . ? H19D C19A H19E 109.5 . . ? C19A C19A H19F 42.9 4_565 . ? C18A C19A H19F 110.5 . . ? C18A C19A H19F 81.1 4_565 . ? H19D C19A H19F 109.5 . . ? H19E C19A H19F 109.5 . . ? H19B C19A H19C 83.2 4_565 4_565 ? C19A C19A H19F 66(8) 4_565 4_565 ? C18A C19A H19F 118(3) . 4_565 ? C18A C19A H19F 98(6) 4_565 4_565 ? H19D C19A H19F 119.5 . 4_565 ? H19E C19A H19F 86.6 . 4_565 ? H19F C19A H19F 22.9 . 4_565 ? H19B C19A H19F 37.7 4_565 4_565 ? H19C C19A H19F 47.2 4_565 4_565 ? 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 N1 1.9655(17) . ? Fe1 N1 1.9656(17) 4_565 ? Fe1 Cl1 2.1911(11) . ? Fe1 Cl2 2.1979(9) . ? N1 C1 1.328(2) . ? N1 C4 1.449(3) . ? C1 C2 1.419(3) . ? C1 C1 1.464(4) 4_565 ? C2 C3 1.356(3) . ? C2 H2 0.9500 . ? C3 C3 1.430(4) 4_565 ? C3 H3 0.9500 . ? C4 C9 1.397(3) . ? C4 C5 1.403(3) . ? C5 C6 1.395(3) . ? C5 C10 1.517(3) . ? C6 C7 1.378(4) . ? C6 H6 0.9500 . ? C7 C8 1.375(4) . ? C7 H7 0.9500 . ? C8 C9 1.395(3) . ? C8 H8 0.9500 . ? C9 C13 1.519(3) . ? C10 C11 1.524(3) . ? C10 C12 1.525(4) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.526(4) . ? C13 C15 1.538(3) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? O1 C16 1.37(3) . ? O1 C18 1.40(3) . ? C16 C17 1.52(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17E 0.48(4) 4_565 ? C18 C19 1.41(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C19 H19F 0.54(5) 4_565 ? O1A O1A 0.75(8) 4_565 ? O1A C18A 1.20(3) . ? O1A C16A 1.26(3) . ? O1A C18A 1.47(5) 4_565 ? O1A C16A 1.47(4) 4_565 ? C16A C16A 0.76(8) 4_565 ? C16A C17A 1.22(4) . ? C16A C17A 1.50(6) 4_565 ? C16A H16C 0.9599 . ? C16A H16D 0.9601 . ? C17A C17A 0.98(10) 4_565 ? C17A H17D 0.9600 . ? C17A H17E 0.9600 . ? C17A H17F 0.9600 . ? C17A H17E 0.71(4) 4_565 ? C18A C18A 0.97(8) 4_565 ? C18A C19A 1.31(3) . ? C18A C19A 1.64(6) 4_565 ? C18A H18C 0.9600 . ? C18A H18D 0.9600 . ? C19A C19A 1.00(11) 4_565 ? C19A H19D 0.9600 . ? C19A H19E 0.9600 . ? C19A H19F 0.9600 . ? C19A H19F 0.72(4) 4_565 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 7.7(3) . . . . ? Fe1 N1 C1 C2 -172.00(18) . . . . ? C4 N1 C1 C1 -170.14(14) . . . 4_565 ? Fe1 N1 C1 C1 10.19(15) . . . 4_565 ? N1 C1 C2 C3 -178.1(2) . . . . ? C1 C1 C2 C3 -0.4(3) 4_565 . . . ? C1 C2 C3 C3 0.4(3) . . . 4_565 ? C1 N1 C4 C9 -92.3(3) . . . . ? Fe1 N1 C4 C9 87.3(2) . . . . ? C1 N1 C4 C5 92.1(2) . . . . ? Fe1 N1 C4 C5 -88.3(2) . . . . ? C9 C4 C5 C6 -0.7(3) . . . . ? N1 C4 C5 C6 174.76(19) . . . . ? C9 C4 C5 C10 178.1(2) . . . . ? N1 C4 C5 C10 -6.4(3) . . . . ? C4 C5 C6 C7 -1.4(4) . . . . ? C10 C5 C6 C7 179.7(2) . . . . ? C5 C6 C7 C8 2.0(4) . . . . ? C6 C7 C8 C9 -0.5(4) . . . . ? C7 C8 C9 C4 -1.6(4) . . . . ? C7 C8 C9 C13 177.0(2) . . . . ? C5 C4 C9 C8 2.2(3) . . . . ? N1 C4 C9 C8 -173.2(2) . . . . ? C5 C4 C9 C13 -176.4(2) . . . . ? N1 C4 C9 C13 8.3(3) . . . . ? C6 C5 C10 C11 -46.4(3) . . . . ? C4 C5 C10 C11 134.8(2) . . . . ? C6 C5 C10 C12 78.5(3) . . . . ? C4 C5 C10 C12 -100.3(3) . . . . ? C8 C9 C13 C14 57.9(3) . . . . ? C4 C9 C13 C14 -123.6(2) . . . . ? C8 C9 C13 C15 -65.5(3) . . . . ? C4 C9 C13 C15 113.0(3) . . . . ? C18 O1 C16 C17 180.000(3) . . . . ? C16 O1 C18 C19 180.000(2) . . . . ? O1A O1A C16A C16A -0.002(12) 4_565 . . 4_565 ? C18A O1A C16A C16A 99(6) . . . 4_565 ? C18A O1A C16A C16A 43(3) 4_565 . . 4_565 ? O1A O1A C16A C17A 97(7) 4_565 . . . ? C18A O1A C16A C17A -164(6) . . . . ? C18A O1A C16A C17A 140(5) 4_565 . . . ? C16A O1A C16A C17A 97(7) 4_565 . . . ? C18A O1A C16A O1A 99(6) . . . 4_565 ? C18A O1A C16A O1A 43(3) 4_565 . . 4_565 ? C16A O1A C16A O1A 0.002(15) 4_565 . . 4_565 ? O1A O1A C16A C17A 42.8(18) 4_565 . . 4_565 ? C18A O1A C16A C17A 141(5) . . . 4_565 ? C18A O1A C16A C17A 86(3) 4_565 . . 4_565 ? C16A O1A C16A C17A 42.8(18) 4_565 . . 4_565 ? C16A C16A C17A C17A 0.000(4) 4_565 . . 4_565 ? O1A C16A C17A C17A -95(6) . . . 4_565 ? O1A C16A C17A C17A -52(3) 4_565 . . 4_565 ? O1A C16A C17A C16A -95(6) . . . 4_565 ? O1A C16A C17A C16A -52(3) 4_565 . . 4_565 ? C17A C16A C17A C16A 0.000(13) 4_565 . . 4_565 ? O1A O1A C18A C18A 0.001(3) 4_565 . . 4_565 ? C16A O1A C18A C18A -97(6) . . . 4_565 ? C16A O1A C18A C18A -52(4) 4_565 . . 4_565 ? O1A O1A C18A C19A -84(6) 4_565 . . . ? C16A O1A C18A C19A 179(6) . . . . ? C18A O1A C18A C19A -84(6) 4_565 . . . ? C16A O1A C18A C19A -136(5) 4_565 . . . ? C16A O1A C18A O1A -97(6) . . . 4_565 ? C18A O1A C18A O1A -0.001(4) 4_565 . . 4_565 ? C16A O1A C18A O1A -52(4) 4_565 . . 4_565 ? O1A O1A C18A C19A -37.8(18) 4_565 . . 4_565 ? C16A O1A C18A C19A -134(5) . . . 4_565 ? C18A O1A C18A C19A -37.8(18) 4_565 . . 4_565 ? C16A O1A C18A C19A -90(3) 4_565 . . 4_565 ? C18A C18A C19A C19A 0.002(5) 4_565 . . 4_565 ? O1A C18A C19A C19A 82(6) . . . 4_565 ? O1A C18A C19A C19A 42(3) 4_565 . . 4_565 ? O1A C18A C19A C18A 82(6) . . . 4_565 ? O1A C18A C19A C18A 42(3) 4_565 . . 4_565 ? C19A C18A C19A C18A -0.002(16) 4_565 . . 4_565 ?