#------------------------------------------------------------------------------ #$Date: 2022-03-03 20:26:26 +0000 (Thu, 03 Mar 2022) $ #$Revision: 273248 $ #$URL: svn://www.crystallography.net/cod/cif/4/51/93/4519341.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_4519341 loop_ _publ_author_name 'Lv, Xiaokang' 'Xu, Jun' 'Sun, Cuiyun' 'Su, Fen' 'Cai, Yuanlin' 'Jin, Zhichao' 'Chi, Yonggui Robin' _publ_section_title ; Access to Planar Chiral Ferrocenes via N-Heterocyclic Carbene-Catalyzed Enantioselective Desymmetrization Reactions ; _journal_issue 4 _journal_name_full 'ACS Catalysis' _journal_page_first 2706 _journal_page_last 2713 _journal_paper_doi 10.1021/acscatal.2c00001 _journal_volume 12 _journal_year 2022 _chemical_formula_moiety 'C21 H19 Fe N O6' _chemical_formula_sum 'C21 H19 Fe N O6' _chemical_formula_weight 437.22 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2021-05-13 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6272) ; _cell_angle_alpha 90 _cell_angle_beta 101.481(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.6105(6) _cell_length_b 8.0429(7) _cell_length_c 15.2788(13) _cell_measurement_reflns_used 2380 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.149 _cell_measurement_theta_min 2.721 _cell_volume 916.51(13) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298.15 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_unetI/netI 0.0564 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 4427 _diffrn_reflns_point_group_measured_fraction_full 0.943 _diffrn_reflns_point_group_measured_fraction_max 0.943 _diffrn_reflns_theta_full 25.018 _diffrn_reflns_theta_max 25.018 _diffrn_reflns_theta_min 2.721 _exptl_absorpt_coefficient_mu 0.864 _exptl_absorpt_correction_T_max 0.7817 _exptl_absorpt_correction_T_min 0.6972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour red _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.584 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 452 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.408 _refine_diff_density_min -0.368 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details ; Flack x determined using 1080 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 3043 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0386 _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^+0.2311P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.0912 _reflns_Friedel_coverage 0.753 _reflns_Friedel_fraction_full 0.879 _reflns_Friedel_fraction_max 0.879 _reflns_number_gt 2743 _reflns_number_total 3043 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file cs2c00001_si_002.cif _cod_data_source_block 210513e _cod_database_code 4519341 _shelx_shelxl_version_number 2018/3 _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_estimated_absorpt_t_max 0.782 _shelx_estimated_absorpt_t_min 0.697 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Ternary CH refined with riding coordinates: C2(H2) 2.b Secondary CH2 refined with riding coordinates: C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B) 2.c Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18) ; _shelx_res_file ; TITL 210513e in P2(1) 210513e.res created by SHELXL-2018/3 at 19:43:05 on 13-May-2021 CELL 0.71073 7.6105 8.0429 15.2788 90 101.481 90 ZERR 2 0.0006 0.0007 0.0013 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Fe N O UNIT 42 38 2 2 12 L.S. 8 PLAN 5 SIZE 0.45 0.38 0.3 TEMP 25 CONF BOND $h fmap 2 acta MORE -1 OMIT -1 50.04 REM REM REM WGHT 0.034800 0.231100 FVAR 0.87978 FE1 3 0.634762 0.654800 0.197706 11.00000 0.03218 0.02890 = 0.03875 -0.00298 0.00520 0.00193 N1 4 0.229561 0.444352 0.405483 11.00000 0.05058 0.06304 = 0.06013 -0.00659 0.00760 0.00612 O1 5 0.557895 0.335609 0.373052 11.00000 0.05629 0.04557 = 0.03779 -0.00245 0.01828 -0.00759 O2 5 0.574290 0.220632 0.242011 11.00000 0.08632 0.04796 = 0.05458 -0.01410 0.03637 -0.02075 O3 5 0.278310 0.534050 0.351117 11.00000 0.07921 0.05445 = 0.10358 0.01492 0.02939 0.00771 O4 5 0.144317 0.493053 0.459180 11.00000 0.08566 0.10029 = 0.10738 -0.01522 0.04717 0.02648 O5 5 0.960956 0.416715 0.096619 11.00000 0.05299 0.04164 = 0.05113 0.00969 0.02230 0.01030 O6 5 0.997658 0.247553 0.219840 11.00000 0.07201 0.04554 = 0.04566 0.00398 0.01169 0.02771 C1 1 0.616252 0.329710 0.294084 11.00000 0.04289 0.03398 = 0.03827 0.00409 0.01114 0.00575 C2 1 0.880913 0.350521 0.163098 11.00000 0.03112 0.04294 = 0.04023 -0.00124 0.00820 0.00201 AFIX 13 H2 2 0.772306 0.289112 0.136254 11.00000 -1.20000 AFIX 0 C3 1 0.726043 0.473174 0.285041 11.00000 0.03617 0.03094 = 0.03206 -0.00260 0.00256 0.00279 C4 1 0.835457 0.487373 0.219666 11.00000 0.03284 0.03251 = 0.04100 -0.00324 0.00393 0.00184 C5 1 0.906471 0.650394 0.227271 11.00000 0.03346 0.04182 = 0.06000 0.00439 0.01007 -0.00379 AFIX 43 H5 2 0.983808 0.694727 0.193283 11.00000 -1.20000 AFIX 0 C6 1 0.841095 0.733624 0.294308 11.00000 0.03773 0.04190 = 0.05781 -0.01015 -0.00770 -0.00522 AFIX 43 H6 2 0.867544 0.842897 0.312080 11.00000 -1.20000 AFIX 0 C7 1 0.730519 0.627571 0.330174 11.00000 0.04249 0.03493 = 0.03984 -0.00956 0.00517 0.00581 AFIX 43 H7 2 0.670072 0.653101 0.375696 11.00000 -1.20000 AFIX 0 C8 1 0.476186 0.601352 0.081444 11.00000 0.09385 0.08409 = 0.05655 -0.02929 -0.02862 0.04981 AFIX 43 H8 2 0.488817 0.507382 0.047767 11.00000 -1.20000 AFIX 0 C9 1 0.555268 0.748904 0.074965 11.00000 0.06117 0.13538 = 0.06305 0.04786 0.03050 0.02866 AFIX 43 H9 2 0.630503 0.775531 0.035951 11.00000 -1.20000 AFIX 0 C10 1 0.503233 0.855579 0.138077 11.00000 0.05823 0.04011 = 0.10646 0.01599 -0.02885 0.00793 AFIX 43 H10 2 0.537302 0.965752 0.149508 11.00000 -1.20000 AFIX 0 C11 1 0.391305 0.762931 0.179439 11.00000 0.04607 0.09111 = 0.05294 0.00132 0.00772 0.02808 AFIX 43 H11 2 0.335596 0.800650 0.224623 11.00000 -1.20000 AFIX 0 C12 1 0.375525 0.611294 0.144610 11.00000 0.03805 0.05906 = 0.09397 0.01358 -0.01970 -0.00551 AFIX 43 H12 2 0.306386 0.525847 0.161052 11.00000 -1.20000 AFIX 0 C13 1 0.436687 0.216562 0.388448 11.00000 0.05424 0.04791 = 0.03223 0.00114 0.01265 -0.01064 C14 1 0.275525 0.269825 0.407552 11.00000 0.05411 0.05188 = 0.03444 0.00034 0.01029 -0.00197 C15 1 0.157547 0.156492 0.430484 11.00000 0.05556 0.08568 = 0.03819 0.00617 0.00974 -0.01967 AFIX 43 H15 2 0.050683 0.192470 0.444891 11.00000 -1.20000 AFIX 0 C16 1 0.196929 -0.007126 0.432076 11.00000 0.08647 0.06888 = 0.04552 0.01377 0.00915 -0.03175 AFIX 43 H16 2 0.115973 -0.084019 0.446520 11.00000 -1.20000 AFIX 0 C17 1 0.354909 -0.060302 0.412602 11.00000 0.11485 0.04648 = 0.04625 0.00962 0.01900 -0.01396 AFIX 43 H17 2 0.380349 -0.173456 0.413480 11.00000 -1.20000 AFIX 0 C18 1 0.477240 0.051487 0.391652 11.00000 0.07344 0.04007 = 0.04676 0.00607 0.01776 0.00175 AFIX 43 H18 2 0.586047 0.014756 0.379855 11.00000 -1.20000 AFIX 0 C19 1 1.008863 0.288447 0.042492 11.00000 0.05482 0.06212 = 0.04576 -0.00192 0.02128 0.00534 AFIX 23 H19A 2 1.067729 0.336253 -0.002383 11.00000 -1.20000 H19B 2 0.901512 0.231784 0.011979 11.00000 -1.20000 AFIX 0 C20 1 1.131280 0.166435 0.097311 11.00000 0.04495 0.04529 = 0.06216 -0.01017 0.01098 0.00986 AFIX 23 H20A 2 1.245915 0.218413 0.120947 11.00000 -1.20000 H20B 2 1.151694 0.072753 0.060614 11.00000 -1.20000 AFIX 0 C21 1 1.046566 0.107484 0.172874 11.00000 0.08062 0.04236 = 0.06401 -0.00083 0.01524 0.02107 AFIX 23 H21A 2 0.941028 0.041448 0.149446 11.00000 -1.20000 H21B 2 1.130573 0.038335 0.213202 11.00000 -1.20000 AFIX 0 HKLF 4 REM 210513e in P2(1) REM wR2 = 0.0912, GooF = S = 1.059, Restrained GooF = 1.059 for all data REM R1 = 0.0386 for 2743 Fo > 4sig(Fo) and 0.0445 for all 3043 data REM 262 parameters refined using 1 restraints END WGHT 0.0348 0.2311 REM Highest difference peak 0.408, deepest hole -0.368, 1-sigma level 0.047 Q1 1 0.5188 0.6514 0.1531 11.00000 0.05 0.41 Q2 1 0.7532 0.6628 0.2411 11.00000 0.05 0.39 Q3 1 0.6897 0.6997 0.1402 11.00000 0.05 0.37 Q4 1 0.6861 0.6082 0.1424 11.00000 0.05 0.32 Q5 1 0.5829 0.7028 0.2478 11.00000 0.05 0.26 ; _shelx_res_checksum 63369 _shelx_hkl_file ; -1 0 0 1287.10 57.49 -2 0 0 500.94 23.05 -2 0 0 488.73 22.42 -3 0 0 132.68 6.70 -3 0 0 135.96 7.67 -4 0 0 481.43 23.22 -4 0 0 528.11 24.70 -5 0 0 206.42 11.98 -6 0 0 23.59 4.55 -7 0 0 2.13 3.68 -8 0 0 188.94 13.37 -9 0 0 23.34 6.97 -9 1 0 51.25 8.07 -8 1 0 11.06 5.21 -7 1 0 1.70 3.67 -6 1 0 64.27 6.06 -5 1 0 246.95 12.75 -5 1 0 255.24 13.94 -4 1 0 87.84 5.46 -4 1 0 88.64 6.23 -3 1 0 677.52 31.20 -3 1 0 657.71 30.64 -2 1 0 113.91 6.33 -2 1 0 126.28 6.66 -1 1 0 3361.00 155.20 -1 1 0 3610.46 154.79 0 1 0 -0.09 0.86 1 1 0 3405.29 151.64 -2 -1 0 184.51 9.71 -2 -1 0 191.30 9.02 -3 -1 0 849.89 37.23 -3 -1 0 801.15 38.29 -4 -1 0 99.49 6.91 -5 -1 0 288.92 15.92 -6 -1 0 79.01 6.90 -7 -1 0 2.20 4.04 -8 -1 0 7.44 5.36 -9 -1 0 57.64 8.87 -9 2 0 5.90 5.33 -8 2 0 62.79 8.10 -7 2 0 83.53 7.63 -6 2 0 39.09 5.56 -5 2 0 135.78 8.84 -5 2 0 135.14 8.29 -4 2 0 883.14 41.06 -4 2 0 886.49 41.41 -3 2 0 619.64 29.43 -3 2 0 631.42 29.39 -2 2 0 1566.97 73.58 -2 2 0 1692.10 73.39 -1 2 0 757.22 35.67 -1 2 0 818.28 36.32 0 2 0 2730.73 128.08 0 -2 0 2918.97 141.71 0 2 0 2998.83 128.93 1 2 0 789.33 36.01 2 2 0 1636.96 73.44 -3 -2 0 636.54 29.70 -3 -2 0 613.98 28.64 -4 -2 0 997.42 46.35 -4 -2 0 980.41 44.82 -5 -2 0 137.13 9.42 -6 -2 0 42.17 6.26 -7 -2 0 111.48 9.04 -8 -2 0 85.46 9.95 -9 -2 0 9.04 5.95 -9 3 0 33.76 6.78 -8 3 0 42.78 6.65 -7 3 0 74.75 7.08 -6 3 0 50.09 6.08 -5 3 0 200.72 12.01 -5 3 0 212.30 11.99 -4 3 0 16.81 3.68 -4 3 0 13.29 3.58 -3 3 0 912.43 41.48 -3 3 0 866.26 41.59 -2 3 0 372.53 18.11 -2 3 0 369.42 18.58 -1 3 0 2402.65 108.66 1 -3 0 2438.29 119.71 -1 3 0 2458.90 109.69 0 3 0 1.87 1.95 0 -3 0 1.37 1.43 1 3 0 2633.52 118.23 2 3 0 370.36 17.98 -3 -3 0 874.02 40.77 -4 -3 0 19.12 3.82 -4 -3 0 9.41 2.99 -5 -3 0 243.26 14.16 -6 -3 0 70.57 7.86 -7 -3 0 89.37 8.55 -8 -3 0 59.47 8.43 -9 -3 0 46.27 8.11 -9 4 0 6.47 4.91 -8 4 0 63.33 7.10 -7 4 0 182.17 12.20 -6 4 0 13.91 4.30 -5 4 0 48.15 6.09 -5 4 0 51.29 6.05 -4 4 0 606.10 29.64 -4 4 0 593.15 29.49 -3 4 0 257.70 13.71 -3 4 0 240.82 13.89 -2 4 0 217.96 12.35 -2 4 0 211.03 11.62 1 -4 0 254.57 12.79 -1 4 0 228.82 13.10 -1 4 0 216.69 12.14 0 -4 0 530.02 29.57 0 4 0 617.84 28.22 1 4 0 237.40 13.10 2 4 0 226.20 12.33 3 4 0 250.16 13.18 -4 -4 0 648.06 31.55 -5 -4 0 42.15 5.81 -6 -4 0 7.63 4.01 -7 -4 0 240.65 15.38 -8 -4 0 67.74 9.06 -9 -4 0 0.85 5.14 -9 5 0 22.81 6.03 -8 5 0 5.18 4.71 -7 5 0 9.78 4.84 -6 5 0 103.95 8.82 -6 5 0 90.77 8.24 -5 5 0 190.15 12.30 -5 5 0 186.06 12.23 -4 5 0 249.06 15.05 -4 5 0 272.73 15.25 -3 5 0 57.37 6.31 -3 5 0 65.80 5.97 -2 5 0 352.19 17.95 -2 5 0 333.03 18.48 -1 5 0 542.51 26.61 -1 5 0 572.49 27.63 1 -5 0 523.75 28.18 0 -5 0 -0.82 2.30 0 5 0 -7.11 3.07 -1 -5 0 579.70 31.90 1 5 0 620.64 29.92 2 5 0 377.52 19.80 3 5 0 66.74 6.22 -4 -5 0 281.41 15.72 -5 -5 0 183.20 11.87 -6 -5 0 119.57 9.56 -7 -5 0 12.91 5.54 -8 -5 0 8.90 5.77 -6 6 0 0.51 4.94 -5 6 0 17.15 5.87 -5 6 0 19.52 5.89 -4 6 0 403.01 22.17 -3 6 0 142.19 10.21 -3 6 0 136.63 10.27 -2 6 0 169.41 11.84 -2 6 0 184.10 11.58 -1 6 0 162.11 11.50 -1 6 0 179.14 11.09 0 6 0 526.62 27.41 1 6 0 178.22 11.87 -1 -6 0 158.05 11.45 -2 -6 0 161.51 11.97 2 6 0 178.13 11.90 3 6 0 137.20 9.98 -4 -6 0 397.99 21.33 -5 -6 0 29.78 5.86 -6 -6 0 5.89 4.80 -7 -6 0 40.34 7.10 -6 7 0 40.16 7.89 -5 7 0 80.25 9.65 -4 7 0 -1.16 5.20 -3 7 0 108.59 9.58 -2 7 0 76.23 8.34 -1 7 0 300.23 18.14 0 7 0 7.32 5.28 1 7 0 305.72 18.52 2 7 0 88.41 9.10 -2 -7 0 90.67 8.99 3 7 0 118.85 10.17 -6 8 0 12.48 6.61 -5 8 0 9.05 6.18 -4 8 0 63.26 9.20 -3 8 0 129.42 11.26 -2 8 0 1.66 5.77 -1 8 0 11.89 6.17 0 8 0 73.90 9.72 1 8 0 17.23 7.00 2 8 0 6.24 5.81 3 8 0 134.28 11.29 -5 9 0 32.76 8.11 -4 9 0 2.74 6.45 -3 9 0 89.64 10.10 -2 9 0 105.38 10.60 -1 9 0 57.97 9.66 0 9 0 0.45 5.93 1 9 0 63.10 9.96 2 9 0 133.79 12.21 3 9 0 100.92 10.96 -3 10 0 18.46 7.17 -2 10 0 10.72 6.86 -1 10 0 25.49 8.07 0 10 0 77.15 11.33 1 10 0 31.89 9.06 2 10 0 20.80 10.08 2 10 -1 39.01 9.19 1 10 -1 47.08 10.12 0 10 -1 14.17 7.60 -1 10 -1 10.76 7.39 -2 10 -1 14.70 7.31 -3 10 -1 39.53 9.06 2 9 -1 9.92 6.90 1 9 -1 23.19 7.34 0 9 -1 119.88 11.47 -1 9 -1 71.04 10.37 -2 9 -1 10.93 6.49 -3 9 -1 48.13 8.71 -4 9 -1 43.52 8.83 -5 9 -1 30.88 8.63 -5 -8 1 77.37 11.13 -4 -8 1 60.99 9.29 3 8 -1 3.23 5.86 2 8 -1 134.36 11.50 1 8 -1 59.86 8.84 0 8 -1 23.98 7.10 -1 8 -1 -2.33 5.42 -2 8 -1 79.32 9.04 -3 8 -1 79.42 9.84 -4 8 -1 5.31 5.96 -5 8 -1 -4.13 5.60 -6 8 -1 46.72 8.91 3 7 -1 375.25 21.36 -3 -7 1 383.69 23.47 -2 -7 1 34.87 6.45 2 7 -1 32.92 6.85 1 7 -1 149.61 11.67 0 7 -1 406.41 22.91 -1 7 -1 191.08 13.20 -2 7 -1 84.68 8.60 -3 7 -1 70.07 8.02 -4 7 -1 111.36 9.81 -5 7 -1 69.05 9.26 -6 7 -1 -5.30 5.76 -8 -6 1 24.15 6.83 -7 -6 1 6.15 4.96 -6 -6 1 51.98 7.23 -5 -6 1 68.29 7.01 -4 -6 1 85.08 7.33 3 6 -1 116.48 9.06 -2 -6 1 503.10 28.28 2 6 -1 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9.77 -5 -3 15 37.55 8.67 -4 -3 15 2.17 6.12 -3 -3 15 -0.40 5.18 2 3 -15 55.79 8.58 -2 -3 15 65.25 9.43 1 3 -15 25.97 6.77 0 3 -15 2.77 4.88 -1 3 -15 23.02 6.32 -2 3 -15 78.19 9.49 -3 3 -15 3.40 5.19 -4 3 -15 9.16 5.73 -8 -2 15 28.54 8.41 -7 -2 15 32.96 8.72 -6 -2 15 18.62 7.25 -5 -2 15 -2.78 5.34 -4 -2 15 27.18 7.19 3 2 -15 80.80 8.89 -3 -2 15 88.99 9.66 2 2 -15 -5.04 4.91 1 2 -15 39.80 7.22 0 2 -15 103.79 9.50 -1 2 -15 92.32 9.06 -2 2 -15 14.41 5.61 -3 2 -15 50.18 7.87 -4 2 -15 29.28 6.55 -6 -1 15 6.60 6.23 -5 -1 15 44.72 8.43 -4 -1 15 31.39 7.56 -3 -1 15 2.45 4.76 3 1 -15 16.32 5.61 2 1 -15 213.99 14.58 1 1 -15 45.30 7.50 0 1 -15 20.79 5.89 -1 1 -15 115.11 10.02 -2 1 -15 254.75 16.30 -3 1 -15 59.64 8.51 -4 1 -15 0.40 4.90 -5 1 -15 11.01 6.73 -8 0 15 6.64 6.08 -6 0 15 7.96 6.13 -5 0 15 0.30 5.32 -4 0 15 7.43 5.40 -4 0 15 6.06 5.44 3 0 -15 47.45 7.98 2 0 -15 139.34 11.56 1 0 -15 165.75 12.63 0 0 -15 12.49 5.60 -1 0 -15 149.72 11.83 -2 0 -15 1.60 5.58 -3 0 -15 55.82 8.43 -4 0 -15 10.99 6.04 -5 0 -15 4.94 6.11 -8 1 15 22.71 7.13 -7 1 15 -0.61 6.06 -6 1 15 -2.80 5.62 -5 1 15 34.47 8.05 -4 1 15 15.33 7.02 3 -1 -15 5.85 5.68 -3 1 15 2.23 4.87 -2 1 15 220.15 14.48 2 -1 -15 228.09 15.02 1 -1 -15 31.10 7.11 0 -1 -15 16.60 6.16 -1 -1 -15 103.17 9.82 -2 -1 -15 251.81 16.23 -3 -1 -15 63.28 9.32 -4 -1 -15 0.31 5.84 -5 -1 -15 4.20 5.71 -7 2 15 37.75 8.28 -6 2 15 13.01 6.95 -5 2 15 2.38 6.66 4 -2 -15 36.63 7.55 -4 2 15 17.20 7.36 3 -2 -15 92.64 9.30 -3 2 15 81.78 9.06 -2 2 15 -11.10 4.95 2 -2 -15 2.70 5.46 1 -2 -15 49.54 8.22 0 -2 -15 127.18 10.76 -1 -2 -15 93.48 9.40 -2 -2 -15 14.15 6.79 -3 -2 -15 63.51 9.41 -4 -2 -15 30.38 8.04 -5 -2 -15 19.14 7.84 -5 -2 -15 17.84 8.25 -7 3 15 0.91 6.82 -6 3 15 29.60 8.51 -5 3 15 32.03 8.45 -4 3 15 -8.78 6.23 4 -3 -15 6.92 6.45 -3 3 15 -10.67 5.68 3 -3 -15 2.66 5.38 2 -3 -15 63.84 8.60 -2 3 15 54.42 8.92 1 -3 -15 37.03 7.42 0 -3 -15 8.77 6.02 -1 -3 -15 29.02 7.93 -2 -3 -15 89.81 9.64 -3 -3 -15 3.25 7.01 -4 -3 -15 0.13 6.32 -6 4 15 28.55 9.44 -5 4 15 -0.18 6.33 -4 4 15 56.16 10.45 4 -4 -15 72.66 10.18 -3 4 15 97.98 10.76 3 -4 -15 86.64 10.72 2 -4 -15 23.21 7.13 1 -4 -15 20.99 6.84 0 -4 -15 52.13 8.87 -1 -4 -15 84.66 9.42 -2 -4 -15 6.48 6.60 -3 -4 -15 15.85 7.50 -4 -4 -15 9.75 7.92 -6 5 15 9.44 8.97 -5 5 15 51.30 10.87 4 -5 -15 34.19 9.20 -4 5 15 37.28 9.74 -3 5 15 11.62 7.09 3 -5 -15 31.37 8.52 2 -5 -15 82.09 10.71 1 -5 -15 75.61 10.74 0 -5 -15 5.31 7.39 -1 -5 -15 2.49 6.31 -2 -5 -15 41.68 9.12 -3 -5 -15 16.04 8.42 -4 6 15 10.68 8.86 4 -6 -15 23.03 9.01 -3 6 15 71.04 12.03 3 -6 -15 88.12 11.77 2 -6 -15 10.91 7.97 1 -6 -15 3.07 7.00 0 -6 -15 10.11 7.60 -1 -6 -15 18.90 8.73 4 -7 -15 15.73 8.06 3 -7 -15 2.56 6.98 2 -7 -15 41.55 9.44 1 -7 -15 45.58 9.32 1 7 -16 17.35 8.72 -3 -6 16 7.78 7.34 1 6 -16 38.80 10.11 0 6 -16 24.37 8.88 -1 6 -16 7.04 7.90 -5 -5 16 1.62 6.99 -4 -5 16 34.89 9.32 -3 -5 16 13.51 6.83 2 5 -16 23.32 8.17 1 5 -16 2.90 7.07 0 5 -16 48.11 9.73 0 5 -16 47.97 9.72 -1 5 -16 37.17 8.60 -1 5 -16 36.91 8.58 -2 5 -16 4.78 5.87 -7 -4 16 1.85 7.33 -6 -4 16 0.77 7.23 -5 -4 16 34.80 8.68 -4 -4 16 -0.18 6.02 -3 -4 16 1.13 5.76 2 4 -16 20.26 7.20 1 4 -16 63.25 9.92 0 4 -16 12.90 6.46 -1 4 -16 9.82 6.15 -2 4 -16 22.62 7.40 -3 4 -16 7.62 6.04 -7 -3 16 7.23 6.86 -6 -3 16 13.35 7.37 -5 -3 16 5.85 7.14 -4 -3 16 13.01 6.60 -3 -3 16 54.92 9.17 2 3 -16 74.02 9.88 1 3 -16 6.62 5.46 0 3 -16 21.33 6.55 -1 3 -16 56.31 8.60 -2 3 -16 0.64 5.15 -3 3 -16 1.38 5.91 -7 -2 16 -3.84 6.36 -6 -2 16 5.79 6.17 -5 -2 16 85.22 11.70 -4 -2 16 74.78 10.69 -3 -2 16 3.75 4.84 3 2 -16 -0.71 5.18 2 2 -16 12.55 6.00 1 2 -16 91.48 9.46 0 2 -16 62.16 8.71 -1 2 -16 41.93 8.06 -2 2 -16 37.76 7.20 -3 2 -16 11.19 6.05 -4 2 -16 3.69 5.37 -6 -1 16 48.76 8.92 -5 -1 16 7.63 6.14 -4 -1 16 55.28 9.38 3 1 -16 90.83 9.60 2 1 -16 41.23 7.50 1 1 -16 1.73 4.89 0 1 -16 101.57 9.66 -1 1 -16 34.98 7.23 -2 1 -16 8.77 5.17 -3 1 -16 9.84 6.10 -4 1 -16 16.10 6.29 -4 0 16 99.06 10.06 3 0 -16 -4.41 5.36 2 0 -16 88.45 9.93 1 0 -16 237.23 15.83 0 0 -16 4.09 5.86 -1 0 -16 10.82 6.43 -2 0 -16 20.94 6.78 -3 0 -16 0.11 5.31 -4 0 -16 11.44 6.28 -7 1 16 16.49 7.51 -5 1 16 8.44 6.98 -4 1 16 59.99 9.16 -3 1 16 77.32 10.12 3 -1 -16 97.34 10.74 2 -1 -16 46.33 8.11 1 -1 -16 1.74 6.23 0 -1 -16 120.65 11.14 -1 -1 -16 46.87 8.36 -2 -1 -16 9.88 6.41 -3 -1 -16 21.45 7.12 -4 -1 -16 19.44 7.30 -7 2 16 1.06 6.99 -6 2 16 7.53 7.05 -5 2 16 68.98 10.76 -4 2 16 58.70 9.70 -3 2 16 -2.53 6.60 3 -2 -16 8.89 6.30 2 -2 -16 20.19 6.75 1 -2 -16 96.19 10.21 0 -2 -16 71.32 9.50 -1 -2 -16 51.91 8.66 -2 -2 -16 43.49 8.41 -3 -2 -16 33.47 8.00 -4 -2 -16 3.18 6.37 -6 3 16 19.60 8.75 -5 3 16 8.82 7.98 4 -3 -16 10.69 6.82 -4 3 16 9.27 7.54 3 -3 -16 43.92 8.34 -3 3 16 43.55 9.11 2 -3 -16 90.84 11.00 1 -3 -16 6.97 5.70 0 -3 -16 38.04 8.14 -1 -3 -16 75.70 10.01 -2 -3 -16 17.05 7.36 -3 -3 -16 -1.29 6.41 -6 4 16 -1.37 8.01 -5 4 16 40.88 9.44 4 -4 -16 13.29 7.48 -4 4 16 7.72 7.58 -3 4 16 4.23 7.36 3 -4 -16 -4.34 6.32 2 -4 -16 18.37 6.85 1 -4 -16 62.84 9.32 0 -4 -16 14.84 7.16 -1 -4 -16 10.21 6.87 -2 -4 -16 40.55 9.04 -3 -4 -16 8.36 7.68 -5 5 16 13.67 8.51 4 -5 -16 39.38 9.22 -4 5 16 22.81 9.66 -3 5 16 10.87 7.92 3 -5 -16 14.84 7.51 2 -5 -16 12.20 7.75 1 -5 -16 5.58 6.64 0 -5 -16 90.68 11.39 -1 -5 -16 57.27 10.12 -2 -5 -16 -0.17 7.32 4 -6 -16 -14.12 8.00 3 -6 -16 22.51 8.98 2 -6 -16 33.57 9.04 1 -6 -16 34.36 8.94 0 -6 -16 16.91 8.08 1 6 -17 -1.36 8.73 0 6 -17 18.19 8.97 -4 -5 17 44.54 9.64 -3 -5 17 1.96 6.15 2 5 -17 4.05 7.46 1 5 -17 25.70 7.93 0 5 -17 2.20 7.13 -1 5 -17 -2.13 6.44 -6 -4 17 19.91 8.08 -5 -4 17 17.96 8.91 -4 -4 17 13.69 6.74 -3 -4 17 36.95 8.58 2 4 -17 58.02 10.03 1 4 -17 -1.63 5.83 0 4 -17 19.09 7.13 -1 4 -17 17.33 7.08 -2 4 -17 1.98 6.40 -7 -3 17 3.62 7.07 -6 -3 17 3.98 7.38 -5 -3 17 19.69 7.67 -4 -3 17 34.78 8.99 -3 -3 17 8.13 5.90 2 3 -17 10.76 5.99 1 3 -17 76.96 10.17 0 3 -17 39.02 7.94 -1 3 -17 1.04 5.18 -2 3 -17 24.39 7.26 -7 -2 17 15.34 7.58 -6 -2 17 21.12 8.01 -5 -2 17 5.22 6.51 -4 -2 17 13.97 6.54 2 2 -17 92.77 10.04 1 2 -17 14.27 6.63 0 2 -17 38.07 7.53 -1 2 -17 80.61 9.70 -2 2 -17 4.81 5.61 -3 2 -17 -1.42 6.02 -5 -1 17 40.00 8.45 -4 -1 17 3.30 5.26 3 1 -17 8.41 5.38 2 1 -17 118.81 11.27 1 1 -17 85.84 9.75 0 1 -17 87.01 10.32 -1 1 -17 14.51 5.81 -2 1 -17 20.89 7.05 -3 1 -17 55.41 8.75 3 0 -17 48.90 8.80 2 0 -17 84.65 10.52 1 0 -17 1.07 5.74 0 0 -17 15.62 6.76 -1 0 -17 20.60 6.91 -2 0 -17 88.50 9.51 -3 0 -17 7.64 6.21 -7 1 17 8.74 7.87 -6 1 17 10.77 8.22 -5 1 17 36.93 9.05 -4 1 17 5.58 6.40 3 -1 -17 12.45 6.42 2 -1 -17 124.25 11.72 1 -1 -17 99.59 10.23 0 -1 -17 76.68 10.28 -1 -1 -17 10.20 6.60 -2 -1 -17 28.91 7.68 -3 -1 -17 37.03 8.18 -7 2 17 -1.07 8.11 -6 2 17 28.48 9.26 -5 2 17 10.00 7.97 -4 2 17 10.12 7.26 3 -2 -17 84.43 10.52 -3 2 17 48.63 9.39 2 -2 -17 92.15 11.09 1 -2 -17 14.42 6.85 0 -2 -17 37.49 8.06 -1 -2 -17 85.71 10.74 -2 -2 -17 4.85 6.59 -3 -2 -17 1.46 6.55 -6 3 17 7.21 8.45 -5 3 17 26.91 9.19 4 -3 -17 31.80 8.42 -4 3 17 40.38 9.42 3 -3 -17 13.06 6.15 -3 3 17 1.65 7.28 2 -3 -17 9.37 6.91 1 -3 -17 75.88 10.27 0 -3 -17 36.04 8.08 -1 -3 -17 -2.04 6.70 -2 -3 -17 13.71 7.33 -5 4 17 24.70 8.67 -4 4 17 -0.24 8.55 4 -4 -17 13.11 7.14 -3 4 17 38.03 9.47 3 -4 -17 30.86 8.33 2 -4 -17 60.20 9.45 1 -4 -17 4.03 6.09 0 -4 -17 25.71 7.85 -1 -4 -17 17.76 7.77 -2 -4 -17 3.32 6.74 -4 5 17 41.50 10.56 4 -5 -17 69.79 11.86 3 -5 -17 1.41 7.42 2 -5 -17 4.00 7.01 1 -5 -17 40.40 8.95 0 -5 -17 -0.99 6.96 4 -6 -17 3.41 8.15 3 -6 -17 4.92 8.16 2 -6 -17 38.92 10.46 1 5 -18 9.42 7.50 0 5 -18 13.30 6.83 -5 -4 18 7.76 7.91 -4 -4 18 33.07 9.58 2 4 -18 8.43 7.52 1 4 -18 23.93 8.10 0 4 -18 22.83 7.39 -1 4 -18 4.07 6.44 -6 -3 18 29.16 9.10 -5 -3 18 4.45 7.31 -4 -3 18 -1.42 6.79 2 3 -18 26.86 8.07 1 3 -18 12.85 6.25 0 3 -18 8.09 5.99 -1 3 -18 17.08 6.97 -6 -2 18 5.11 7.45 -5 -2 18 27.75 8.86 -4 -2 18 79.02 11.56 2 2 -18 7.19 5.92 1 2 -18 19.09 6.51 0 2 -18 16.91 6.43 -1 2 -18 6.08 5.73 -2 2 -18 24.13 7.34 3 1 -18 50.82 8.54 2 1 -18 69.70 9.74 1 1 -18 3.36 5.26 0 1 -18 9.12 5.89 -1 1 -18 33.36 7.06 -2 1 -18 22.91 7.60 3 0 -18 45.49 8.78 2 0 -18 12.29 6.87 1 0 -18 78.86 10.83 0 0 -18 4.34 6.39 -1 0 -18 39.16 8.13 -2 0 -18 17.03 6.65 3 -1 -18 50.68 9.46 2 -1 -18 54.88 9.39 1 -1 -18 -1.20 6.01 0 -1 -18 2.91 6.43 -1 -1 -18 27.52 8.09 -2 -1 -18 33.90 8.69 -6 2 18 13.74 9.13 -5 2 18 5.67 8.41 3 -2 -18 22.30 8.08 -3 2 18 27.93 8.34 2 -2 -18 10.25 6.60 1 -2 -18 9.79 7.09 0 -2 -18 21.75 7.99 -1 -2 -18 4.99 6.44 -2 -2 -18 40.82 8.47 -5 3 18 15.97 9.14 -4 3 18 -0.62 8.02 3 -3 -18 20.11 7.48 2 -3 -18 30.58 7.85 1 -3 -18 4.16 6.69 0 -3 -18 8.70 7.02 -1 -3 -18 13.28 7.43 -4 4 18 28.88 9.93 3 -4 -18 8.10 6.88 2 -4 -18 9.59 6.68 1 -4 -18 22.82 7.89 0 -4 -18 34.74 9.13 4 -5 -18 11.75 7.95 3 -5 -18 72.04 11.64 2 -5 -18 9.95 7.57 1 -5 -18 3.93 7.28 2 4 -19 28.46 8.77 1 4 -19 10.60 7.13 -5 -3 19 8.69 7.00 -4 -3 19 4.57 7.01 2 3 -19 6.01 6.58 1 3 -19 5.48 7.00 0 3 -19 22.64 7.66 -5 -2 19 28.63 8.65 2 2 -19 53.60 9.46 1 2 -19 37.51 7.72 0 2 -19 4.16 5.83 -1 2 -19 13.40 6.57 2 1 -19 10.61 5.86 1 1 -19 8.11 5.56 0 1 -19 37.14 7.48 -1 1 -19 22.85 7.06 3 0 -19 42.00 9.00 2 0 -19 45.49 9.22 1 0 -19 35.47 8.26 0 0 -19 9.99 7.09 -1 0 -19 6.38 6.51 3 -1 -19 17.03 7.61 2 -1 -19 -0.81 6.15 1 -1 -19 16.01 6.98 0 -1 -19 22.98 7.97 -1 -1 -19 4.61 6.84 -5 2 19 41.19 10.27 -4 2 19 6.34 8.45 3 -2 -19 13.72 7.66 2 -2 -19 49.58 9.83 1 -2 -19 26.23 8.13 0 -2 -19 1.25 6.88 -4 3 19 30.06 10.35 3 -3 -19 31.98 8.68 2 -3 -19 10.22 7.00 1 -3 -19 4.98 7.55 0 -3 -19 17.96 7.91 3 -4 -19 2.06 7.01 2 -4 -19 10.72 7.46 2 3 -20 19.59 7.80 1 3 -20 23.36 7.36 2 2 -20 10.98 7.49 1 2 -20 19.92 6.88 2 1 -20 21.51 7.43 1 1 -20 11.46 6.71 0 1 -20 1.20 6.56 2 0 -20 34.99 8.61 1 0 -20 8.00 6.81 0 0 -20 10.45 6.63 3 -1 -20 13.73 7.81 2 -1 -20 6.19 6.75 1 -1 -20 5.15 6.67 3 -2 -20 9.24 8.06 2 -2 -20 6.60 6.86 1 -2 -20 22.91 7.73 3 -3 -20 -3.30 7.27 2 -3 -20 13.50 8.29 2 1 -21 16.75 7.36 2 0 -21 29.83 7.72 2 -1 -21 8.57 7.31 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 41112 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz '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 0.63476(8) 0.65480(8) 0.19771(4) 0.0335(2) Uani 1 1 d . . . . . N1 N 0.2296(7) 0.4444(8) 0.4055(4) 0.0584(14) Uani 1 1 d . . . . . O1 O 0.5579(5) 0.3356(5) 0.3731(2) 0.0453(10) Uani 1 1 d . . . . . O2 O 0.5743(6) 0.2206(5) 0.2420(3) 0.0599(13) Uani 1 1 d . . . . . O3 O 0.2783(7) 0.5340(7) 0.3511(4) 0.0775(15) Uani 1 1 d . . . . . O4 O 0.1443(8) 0.4931(8) 0.4592(4) 0.0939(19) Uani 1 1 d . . . . . O5 O 0.9610(5) 0.4167(5) 0.0966(3) 0.0469(10) Uani 1 1 d . . . . . O6 O 0.9977(6) 0.2476(5) 0.2198(3) 0.0544(11) Uani 1 1 d . . . . . C1 C 0.6163(7) 0.3297(7) 0.2941(4) 0.0380(12) Uani 1 1 d . . . . . C2 C 0.8809(7) 0.3505(7) 0.1631(4) 0.0379(12) Uani 1 1 d . . . . . H2 H 0.772306 0.289112 0.136254 0.046 Uiso 1 1 calc R U . . . C3 C 0.7260(7) 0.4732(7) 0.2850(3) 0.0336(11) Uani 1 1 d . . . . . C4 C 0.8355(7) 0.4874(7) 0.2197(4) 0.0359(12) Uani 1 1 d . . . . . C5 C 0.9065(6) 0.6504(11) 0.2273(4) 0.0450(12) Uani 1 1 d . . . . . H5 H 0.983808 0.694727 0.193283 0.054 Uiso 1 1 calc R U . . . C6 C 0.8411(7) 0.7336(8) 0.2943(4) 0.0482(15) Uani 1 1 d . . . . . H6 H 0.867544 0.842897 0.312080 0.058 Uiso 1 1 calc R U . . . C7 C 0.7305(7) 0.6276(7) 0.3302(3) 0.0395(14) Uani 1 1 d . . . . . H7 H 0.670072 0.653101 0.375696 0.047 Uiso 1 1 calc R U . . . C8 C 0.4762(13) 0.6014(12) 0.0814(6) 0.084(3) Uani 1 1 d . . . . . H8 H 0.488817 0.507382 0.047767 0.101 Uiso 1 1 calc R U . . . C9 C 0.5553(10) 0.7489(16) 0.0750(6) 0.084(3) Uani 1 1 d . . . . . H9 H 0.630503 0.775531 0.035951 0.101 Uiso 1 1 calc R U . . . C10 C 0.5032(10) 0.8556(10) 0.1381(6) 0.075(2) Uani 1 1 d . . . . . H10 H 0.537302 0.965752 0.149508 0.089 Uiso 1 1 calc R U . . . C11 C 0.3913(9) 0.7629(12) 0.1794(5) 0.064(2) Uani 1 1 d . . . . . H11 H 0.335596 0.800650 0.224623 0.076 Uiso 1 1 calc R U . . . C12 C 0.3755(9) 0.6113(9) 0.1446(6) 0.068(2) Uani 1 1 d . . . . . H12 H 0.306386 0.525847 0.161052 0.082 Uiso 1 1 calc R U . . . C13 C 0.4367(9) 0.2166(9) 0.3884(4) 0.0442(16) Uani 1 1 d . . . . . C14 C 0.2755(8) 0.2698(8) 0.4076(4) 0.0466(15) Uani 1 1 d . . . . . C15 C 0.1575(8) 0.1565(14) 0.4305(3) 0.0598(16) Uani 1 1 d . . . . . H15 H 0.050683 0.192470 0.444891 0.072 Uiso 1 1 calc R U . . . C16 C 0.1969(11) -0.0071(11) 0.4321(5) 0.068(2) Uani 1 1 d . . . . . H16 H 0.115973 -0.084019 0.446520 0.081 Uiso 1 1 calc R U . . . C17 C 0.3549(12) -0.0603(10) 0.4126(4) 0.069(2) Uani 1 1 d . . . . . H17 H 0.380349 -0.173456 0.413480 0.083 Uiso 1 1 calc R U . . . C18 C 0.4772(10) 0.0515(8) 0.3917(5) 0.0526(18) Uani 1 1 d . . . . . H18 H 0.586047 0.014756 0.379855 0.063 Uiso 1 1 calc R U . . . C19 C 1.0089(8) 0.2884(9) 0.0425(4) 0.0527(16) Uani 1 1 d . . . . . H19A H 1.067729 0.336253 -0.002383 0.063 Uiso 1 1 calc R U . . . H19B H 0.901512 0.231784 0.011979 0.063 Uiso 1 1 calc R U . . . C20 C 1.1313(7) 0.1664(11) 0.0973(4) 0.0508(14) Uani 1 1 d . . . . . H20A H 1.245915 0.218413 0.120947 0.061 Uiso 1 1 calc R U . . . H20B H 1.151694 0.072753 0.060614 0.061 Uiso 1 1 calc R U . . . C21 C 1.0466(11) 0.1075(8) 0.1729(5) 0.0622(19) Uani 1 1 d . . . . . H21A H 0.941028 0.041448 0.149446 0.075 Uiso 1 1 calc R U . . . H21B H 1.130573 0.038335 0.213202 0.075 Uiso 1 1 calc R U . . . 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 0.0322(3) 0.0289(4) 0.0388(4) -0.0030(4) 0.0052(2) 0.0019(4) N1 0.051(3) 0.063(4) 0.060(4) -0.007(3) 0.008(3) 0.006(3) O1 0.056(2) 0.046(2) 0.038(2) -0.0024(19) 0.0183(18) -0.008(2) O2 0.086(3) 0.048(3) 0.055(3) -0.014(2) 0.036(2) -0.021(2) O3 0.079(3) 0.054(3) 0.104(4) 0.015(3) 0.029(3) 0.008(3) O4 0.086(4) 0.100(5) 0.107(5) -0.015(4) 0.047(4) 0.026(4) O5 0.053(2) 0.042(2) 0.051(2) 0.0097(19) 0.0223(19) 0.0103(19) O6 0.072(3) 0.046(2) 0.046(2) 0.004(2) 0.012(2) 0.028(2) C1 0.043(3) 0.034(3) 0.038(3) 0.004(3) 0.011(2) 0.006(2) C2 0.031(3) 0.043(3) 0.040(3) -0.001(3) 0.008(2) 0.002(2) C3 0.036(3) 0.031(3) 0.032(3) -0.003(2) 0.003(2) 0.003(2) C4 0.033(3) 0.033(3) 0.041(3) -0.003(2) 0.004(2) 0.002(2) C5 0.033(2) 0.042(3) 0.060(3) 0.004(4) 0.010(2) -0.004(4) C6 0.038(3) 0.042(3) 0.058(4) -0.010(3) -0.008(3) -0.005(3) C7 0.042(3) 0.035(4) 0.040(3) -0.010(3) 0.005(2) 0.006(3) C8 0.094(7) 0.084(7) 0.057(5) -0.029(4) -0.029(5) 0.050(5) C9 0.061(5) 0.135(9) 0.063(5) 0.048(6) 0.031(4) 0.029(6) C10 0.058(4) 0.040(4) 0.106(6) 0.016(4) -0.029(4) 0.008(3) C11 0.046(4) 0.091(7) 0.053(4) 0.001(4) 0.008(3) 0.028(4) C12 0.038(3) 0.059(6) 0.094(6) 0.014(4) -0.020(4) -0.006(3) C13 0.054(4) 0.048(4) 0.032(3) 0.001(2) 0.013(3) -0.011(3) C14 0.054(4) 0.052(4) 0.034(3) 0.000(3) 0.010(3) -0.002(3) C15 0.056(3) 0.086(5) 0.038(3) 0.006(5) 0.010(2) -0.020(5) C16 0.086(6) 0.069(6) 0.046(4) 0.014(4) 0.009(4) -0.032(5) C17 0.115(7) 0.046(4) 0.046(4) 0.010(3) 0.019(4) -0.014(5) C18 0.073(5) 0.040(4) 0.047(4) 0.006(3) 0.018(3) 0.002(4) C19 0.055(4) 0.062(5) 0.046(3) -0.002(3) 0.021(3) 0.005(3) C20 0.045(3) 0.045(3) 0.062(3) -0.010(4) 0.011(2) 0.010(4) C21 0.081(5) 0.042(5) 0.064(4) -0.001(3) 0.015(4) 0.021(3) 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' 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' 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 C3 Fe1 C4 41.6(2) . . ? C3 Fe1 C5 68.7(3) . . ? C3 Fe1 C6 68.2(3) . . ? C3 Fe1 C7 41.2(2) . . ? C3 Fe1 C10 163.1(3) . . ? C3 Fe1 C11 126.4(3) . . ? C3 Fe1 C12 108.9(3) . . ? C4 Fe1 C5 41.0(3) . . ? C4 Fe1 C6 68.7(2) . . ? C4 Fe1 C7 69.5(2) . . ? C4 Fe1 C10 154.4(3) . . ? C4 Fe1 C11 163.3(3) . . ? C5 Fe1 C6 40.2(2) . . ? C7 Fe1 C5 68.1(2) . . ? C7 Fe1 C6 40.0(2) . . ? C8 Fe1 C3 120.4(3) . . ? C8 Fe1 C4 108.1(3) . . ? C8 Fe1 C5 127.4(3) . . ? C8 Fe1 C6 164.2(4) . . ? C8 Fe1 C7 154.9(4) . . ? C8 Fe1 C9 39.4(4) . . ? C8 Fe1 C10 67.1(3) . . ? C8 Fe1 C11 65.9(3) . . ? C8 Fe1 C12 39.5(4) . . ? C9 Fe1 C3 154.0(4) . . ? C9 Fe1 C4 119.1(3) . . ? C9 Fe1 C5 108.7(3) . . ? C9 Fe1 C6 127.5(4) . . ? C9 Fe1 C7 163.9(4) . . ? C9 Fe1 C10 40.9(4) . . ? C9 Fe1 C11 67.0(3) . . ? C9 Fe1 C12 66.3(3) . . ? C10 Fe1 C5 120.4(3) . . ? C10 Fe1 C6 108.7(3) . . ? C10 Fe1 C7 125.9(3) . . ? C11 Fe1 C5 155.1(3) . . ? C11 Fe1 C6 121.5(3) . . ? C11 Fe1 C7 108.9(3) . . ? C11 Fe1 C10 39.9(3) . . ? C12 Fe1 C4 127.0(3) . . ? C12 Fe1 C5 164.4(3) . . ? C12 Fe1 C6 154.6(3) . . ? C12 Fe1 C7 121.0(3) . . ? C12 Fe1 C10 66.3(3) . . ? C12 Fe1 C11 38.5(3) . . ? O3 N1 C14 119.1(6) . . ? O4 N1 O3 123.4(7) . . ? O4 N1 C14 117.4(7) . . ? C1 O1 C13 118.1(5) . . ? C2 O5 C19 110.4(4) . . ? C2 O6 C21 110.9(5) . . ? O1 C1 C3 110.6(5) . . ? O2 C1 O1 121.8(5) . . ? O2 C1 C3 127.6(5) . . ? O5 C2 H2 110.1 . . ? O5 C2 C4 109.2(5) . . ? O6 C2 O5 111.5(4) . . ? O6 C2 H2 110.1 . . ? O6 C2 C4 105.9(4) . . ? C4 C2 H2 110.1 . . ? C1 C3 Fe1 120.9(4) . . ? C4 C3 Fe1 69.5(3) . . ? C4 C3 C1 124.0(5) . . ? C7 C3 Fe1 70.0(3) . . ? C7 C3 C1 127.6(5) . . ? C7 C3 C4 108.0(5) . . ? C2 C4 Fe1 131.1(4) . . ? C3 C4 Fe1 69.0(3) . . ? C3 C4 C2 125.8(5) . . ? C5 C4 Fe1 70.0(3) . . ? C5 C4 C2 127.3(5) . . ? C5 C4 C3 106.5(5) . . ? Fe1 C5 H5 126.9 . . ? C4 C5 Fe1 69.0(3) . . ? C4 C5 H5 125.7 . . ? C6 C5 Fe1 70.0(3) . . ? C6 C5 C4 108.6(5) . . ? C6 C5 H5 125.7 . . ? Fe1 C6 H6 126.8 . . ? C5 C6 Fe1 69.7(3) . . ? C5 C6 H6 125.4 . . ? C7 C6 Fe1 69.7(3) . . ? C7 C6 C5 109.2(6) . . ? C7 C6 H6 125.4 . . ? Fe1 C7 H7 126.3 . . ? C3 C7 Fe1 68.8(3) . . ? C3 C7 H7 126.1 . . ? C6 C7 Fe1 70.3(3) . . ? C6 C7 C3 107.7(5) . . ? C6 C7 H7 126.1 . . ? Fe1 C8 H8 124.0 . . ? C9 C8 Fe1 70.9(5) . . ? C9 C8 H8 125.5 . . ? C9 C8 C12 109.1(7) . . ? C12 C8 Fe1 71.2(4) . . ? C12 C8 H8 125.5 . . ? Fe1 C9 H9 125.3 . . ? C8 C9 Fe1 69.7(5) . . ? C8 C9 H9 126.4 . . ? C8 C9 C10 107.3(7) . . ? C10 C9 Fe1 70.2(4) . . ? C10 C9 H9 126.4 . . ? Fe1 C10 H10 125.6 . . ? C9 C10 Fe1 68.9(4) . . ? C9 C10 H10 127.2 . . ? C11 C10 Fe1 69.9(4) . . ? C11 C10 C9 105.6(7) . . ? C11 C10 H10 127.2 . . ? Fe1 C11 H11 125.5 . . ? C10 C11 Fe1 70.2(4) . . ? C10 C11 H11 125.4 . . ? C12 C11 Fe1 70.5(5) . . ? C12 C11 C10 109.2(7) . . ? C12 C11 H11 125.4 . . ? Fe1 C12 H12 125.6 . . ? C8 C12 Fe1 69.3(4) . . ? C8 C12 H12 125.6 . . ? C11 C12 Fe1 71.0(5) . . ? C11 C12 C8 108.8(8) . . ? C11 C12 H12 125.6 . . ? O1 C13 C14 118.1(6) . . ? C18 C13 O1 121.8(7) . . ? C18 C13 C14 119.9(6) . . ? C13 C14 N1 121.1(6) . . ? C15 C14 N1 118.9(7) . . ? C15 C14 C13 120.0(7) . . ? C14 C15 H15 120.1 . . ? C16 C15 C14 119.9(7) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.3(7) . . ? C17 C16 H16 119.9 . . ? C16 C17 H17 119.6 . . ? C16 C17 C18 120.8(8) . . ? C18 C17 H17 119.6 . . ? C13 C18 C17 119.1(7) . . ? C13 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? O5 C19 C20 110.9(5) . . ? H19A C19 H19B 108.0 . . ? C20 C19 H19A 109.5 . . ? C20 C19 H19B 109.5 . . ? C19 C20 H20A 109.9 . . ? C19 C20 H20B 109.9 . . ? C19 C20 C21 108.8(5) . . ? H20A C20 H20B 108.3 . . ? C21 C20 H20A 109.9 . . ? C21 C20 H20B 109.9 . . ? O6 C21 C20 109.4(5) . . ? O6 C21 H21A 109.8 . . ? O6 C21 H21B 109.8 . . ? C20 C21 H21A 109.8 . . ? C20 C21 H21B 109.8 . . ? H21A C21 H21B 108.2 . . ? 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 C3 2.007(5) . ? Fe1 C4 2.014(5) . ? Fe1 C5 2.027(5) . ? Fe1 C6 2.031(5) . ? Fe1 C7 2.022(5) . ? Fe1 C8 1.986(7) . ? Fe1 C9 2.001(8) . ? Fe1 C10 2.019(7) . ? Fe1 C11 2.015(7) . ? Fe1 C12 2.009(6) . ? N1 O3 1.213(7) . ? N1 O4 1.208(7) . ? N1 C14 1.445(9) . ? O1 C1 1.367(6) . ? O1 C13 1.382(7) . ? O2 C1 1.185(7) . ? O5 C2 1.390(6) . ? O5 C19 1.415(7) . ? O6 C2 1.386(7) . ? O6 C21 1.424(7) . ? C1 C3 1.447(8) . ? C2 H2 0.9800 . ? C2 C4 1.482(8) . ? C3 C4 1.427(7) . ? C3 C7 1.418(8) . ? C4 C5 1.414(10) . ? C5 H5 0.9300 . ? C5 C6 1.396(8) . ? C6 H6 0.9300 . ? C6 C7 1.386(8) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C8 C9 1.343(12) . ? C8 C12 1.349(12) . ? C9 H9 0.9300 . ? C9 C10 1.405(13) . ? C10 H10 0.9300 . ? C10 C11 1.376(11) . ? C11 H11 0.9300 . ? C11 C12 1.326(11) . ? C12 H12 0.9300 . ? C13 C14 1.384(9) . ? C13 C18 1.362(9) . ? C14 C15 1.373(9) . ? C15 H15 0.9300 . ? C15 C16 1.349(13) . ? C16 H16 0.9300 . ? C16 C17 1.364(11) . ? C17 H17 0.9300 . ? C17 C18 1.377(10) . ? C18 H18 0.9300 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 C20 1.491(10) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C20 C21 1.507(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? 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 C3 C4 C2 -126.2(5) . . . . ? Fe1 C3 C4 C5 60.3(4) . . . . ? Fe1 C3 C7 C6 -59.8(4) . . . . ? Fe1 C4 C5 C6 59.0(4) . . . . ? Fe1 C5 C6 C7 58.6(4) . . . . ? Fe1 C6 C7 C3 58.9(4) . . . . ? Fe1 C8 C9 C10 -60.5(5) . . . . ? Fe1 C8 C12 C11 60.3(6) . . . . ? Fe1 C9 C10 C11 -60.6(5) . . . . ? Fe1 C10 C11 C12 -59.9(6) . . . . ? Fe1 C11 C12 C8 -59.2(5) . . . . ? N1 C14 C15 C16 179.4(6) . . . . ? O1 C1 C3 Fe1 -108.2(4) . . . . ? O1 C1 C3 C4 166.9(5) . . . . ? O1 C1 C3 C7 -20.6(8) . . . . ? O1 C13 C14 N1 4.2(9) . . . . ? O1 C13 C14 C15 -174.6(5) . . . . ? O1 C13 C18 C17 176.1(5) . . . . ? O2 C1 C3 Fe1 70.0(7) . . . . ? O2 C1 C3 C4 -14.8(9) . . . . ? O2 C1 C3 C7 157.6(6) . . . . ? O3 N1 C14 C13 34.4(9) . . . . ? O3 N1 C14 C15 -146.7(6) . . . . ? O4 N1 C14 C13 -145.2(7) . . . . ? O4 N1 C14 C15 33.7(9) . . . . ? O5 C2 C4 Fe1 76.6(6) . . . . ? O5 C2 C4 C3 168.9(5) . . . . ? O5 C2 C4 C5 -18.9(8) . . . . ? O5 C19 C20 C21 52.9(8) . . . . ? O6 C2 C4 Fe1 -163.3(4) . . . . ? O6 C2 C4 C3 -70.9(6) . . . . ? O6 C2 C4 C5 101.3(6) . . . . ? C1 O1 C13 C14 -123.7(6) . . . . ? C1 O1 C13 C18 61.1(9) . . . . ? C1 C3 C4 Fe1 114.1(5) . . . . ? C1 C3 C4 C2 -12.0(8) . . . . ? C1 C3 C4 C5 174.5(5) . . . . ? C1 C3 C7 Fe1 -114.2(5) . . . . ? C1 C3 C7 C6 -174.0(5) . . . . ? C2 O5 C19 C20 -57.4(6) . . . . ? C2 O6 C21 C20 58.0(7) . . . . ? C2 C4 C5 Fe1 127.0(6) . . . . ? C2 C4 C5 C6 -174.0(5) . . . . ? C3 C4 C5 Fe1 -59.6(3) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C4 C3 C7 Fe1 59.2(4) . . . . ? C4 C3 C7 C6 -0.6(6) . . . . ? C4 C5 C6 Fe1 -58.4(4) . . . . ? C4 C5 C6 C7 0.3(6) . . . . ? C5 C6 C7 Fe1 -58.7(4) . . . . ? C5 C6 C7 C3 0.2(6) . . . . ? C7 C3 C4 Fe1 -59.6(4) . . . . ? C7 C3 C4 C2 174.3(5) . . . . ? C7 C3 C4 C5 0.8(6) . . . . ? C8 C9 C10 Fe1 60.1(6) . . . . ? C8 C9 C10 C11 -0.5(9) . . . . ? C9 C8 C12 Fe1 -61.1(6) . . . . ? C9 C8 C12 C11 -0.8(9) . . . . ? C9 C10 C11 Fe1 59.9(5) . . . . ? C9 C10 C11 C12 0.0(8) . . . . ? C10 C11 C12 Fe1 59.8(5) . . . . ? C10 C11 C12 C8 0.5(9) . . . . ? C12 C8 C9 Fe1 61.3(5) . . . . ? C12 C8 C9 C10 0.8(9) . . . . ? C13 O1 C1 O2 -4.7(8) . . . . ? C13 O1 C1 C3 173.7(5) . . . . ? C13 C14 C15 C16 -1.7(9) . . . . ? C14 C13 C18 C17 1.0(12) . . . . ? C14 C15 C16 C17 1.2(10) . . . . ? C15 C16 C17 C18 0.5(10) . . . . ? C16 C17 C18 C13 -1.6(11) . . . . ? C18 C13 C14 N1 179.4(7) . . . . ? C18 C13 C14 C15 0.6(10) . . . . ? C19 O5 C2 O6 62.3(6) . . . . ? C19 O5 C2 C4 178.9(5) . . . . ? C19 C20 C21 O6 -52.7(8) . . . . ? C21 O6 C2 O5 -63.2(6) . . . . ? C21 O6 C2 C4 178.2(5) . . . . ?