#------------------------------------------------------------------------------ #$Date: 2024-06-01 01:16:53 +0300 (Sat, 01 Jun 2024) $ #$Revision: 292137 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571755.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_1571755 loop_ _publ_author_name 'Li, Wei' 'Yu, Jing' 'Wang, Jing' 'Fan, Xuejing' 'Xu, Ximing' 'Wang, Hui' 'Xiong, Ying' 'Li, Xinyu' 'Zhang, Xiaomin' 'Zhang, Qianer' 'Qi, Xin' 'Pigeon, Pascal' 'Gu, Qing' 'Bruno-Colmenarez, Julia' 'Jaouen, Gerard' 'McGlinchey, Michael James' 'Qiu, Xue' 'You, Shu-Li' 'Li, Jing' 'Wang, Yong' _publ_section_title ; How Does Ferrocene Correlate with Ferroptosis? Multiple Approaches to Explore Ferrocene-Appended GPX4 Inhibitors as Anticancer Agents ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02002B _journal_year 2024 _chemical_formula_sum 'C30 H27 Cl Fe N2 O3' _chemical_formula_weight 554.83 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-11-28 deposited with the CCDC. 2024-05-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.242(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 19.7467(5) _cell_length_b 13.7604(3) _cell_length_c 19.3018(5) _cell_measurement_temperature 293(2) _cell_volume 5230.4(2) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.973 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54186 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_unetI/netI 0.0195 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.973 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 16531 _diffrn_reflns_point_group_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 67.686 _diffrn_reflns_theta_max 68.693 _diffrn_reflns_theta_min 3.919 _exptl_absorpt_coefficient_mu 5.845 _exptl_crystal_density_diffrn 1.409 _exptl_crystal_F_000 2304 _refine_diff_density_max 0.374 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.048 _refine_ls_extinction_coef 0.00033(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 443 _refine_ls_number_reflns 4711 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.082 _refine_ls_R_factor_all 0.0513 _refine_ls_R_factor_gt 0.0402 _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^)+(0.0416P)^2^+8.4356P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0950 _refine_ls_wR_factor_ref 0.1090 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4046 _reflns_number_total 4711 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02002b2.cif _cod_data_source_block shelx _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 1571755 _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_res_file ; TITL l11_a.res in C2/c shelx.res created by SHELXL-2018/3 at 10:42:23 on 18-Oct-2022 CELL 1.54186 19.7467 13.7604 19.3018 90.000 94.242 90.000 ZERR 8.00 0.0005 0.0003 0.0005 0.000 0.002 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H CL FE N O UNIT 240 216 8 8 16 24 MERG 2 DFIX 0.930 0.020 C5 H5 FMAP 2 53 53 PLAN 15 ACTA BOND $H EQIV $1 .5-X, 1.5-Y, 1-Z HTAB N1 O2_$1 CONF LIST 4 L.S. 4 WGHT 0.041600 8.435599 EXTI 0.000329 FVAR 0.21526 FE1 4 0.455244 0.648661 0.383762 11.00000 0.03832 0.04239 = 0.04901 0.00171 0.00183 -0.00252 CL1 3 0.195686 0.352676 0.219677 11.00000 0.13647 0.06054 = 0.06044 -0.00546 -0.03580 -0.01255 O1 6 0.359933 0.519702 0.559794 11.00000 0.09344 0.05017 = 0.05309 0.00600 -0.00935 -0.00355 O2 6 0.199155 0.640350 0.511141 11.00000 0.05121 0.05267 = 0.06921 -0.01216 0.01102 -0.00221 O3 6 0.232376 0.186554 0.303243 11.00000 0.10082 0.03905 = 0.06057 -0.00852 -0.00093 -0.01113 N1 5 0.356486 0.683052 0.562245 11.00000 0.06232 0.05162 = 0.05071 -0.00973 -0.00867 0.00150 N2 5 0.257599 0.537365 0.446330 11.00000 0.04143 0.03715 = 0.05129 -0.00700 0.00166 -0.00668 C1 1 0.452658 0.787263 0.417550 11.00000 0.05215 0.05754 = 0.10834 -0.03142 0.01865 -0.01263 C2 1 0.478859 0.785463 0.353296 11.00000 0.07159 0.04897 = 0.07573 0.00666 -0.00156 -0.01055 C3 1 0.536822 0.728906 0.357847 11.00000 0.06411 0.06829 = 0.10205 -0.01303 0.03299 -0.02083 C4 1 0.547085 0.694615 0.425383 11.00000 0.05068 0.07342 = 0.13434 0.01810 -0.02822 -0.01241 C5 1 0.494819 0.731892 0.462550 11.00000 0.10369 0.10404 = 0.05281 -0.00613 -0.00460 -0.06022 C6 1 0.369782 0.574619 0.405377 11.00000 0.04100 0.03552 = 0.04750 -0.00018 -0.00107 -0.00439 C7 1 0.366744 0.601131 0.334035 11.00000 0.05013 0.04862 = 0.04549 0.00045 -0.00390 -0.00963 C8 1 0.422638 0.558733 0.303970 11.00000 0.06931 0.05922 = 0.05260 -0.01145 0.01279 -0.01307 C9 1 0.460402 0.506173 0.355661 11.00000 0.05494 0.05004 = 0.08399 -0.00857 0.01714 0.00682 C10 1 0.428493 0.515022 0.418450 11.00000 0.05108 0.03462 = 0.06464 0.00826 0.00131 0.00237 C11 1 0.318085 0.601836 0.455134 11.00000 0.04068 0.03555 = 0.04745 -0.00285 -0.00005 -0.00560 C12 1 0.346902 0.597063 0.531492 11.00000 0.04360 0.04914 = 0.04807 -0.00568 0.00116 -0.00457 C13 1 0.381602 0.691523 0.635379 11.00000 0.07508 0.07165 = 0.05336 -0.01630 -0.01600 0.01053 C14 1 0.364939 0.787599 0.663358 11.00000 0.09573 0.07347 = 0.05350 -0.01513 -0.01525 0.01683 C15 1 0.393982 0.808730 0.736418 11.00000 0.06481 0.06852 = 0.04657 -0.00914 -0.00337 0.01153 C16 1 0.403477 0.736806 0.786697 11.00000 0.08598 0.06945 = 0.05526 -0.00153 -0.00582 0.00542 C17 1 0.429047 0.760181 0.853239 11.00000 0.08735 0.08942 = 0.05328 -0.00222 -0.00500 0.00778 C18 1 0.444789 0.853380 0.870516 11.00000 0.09502 0.09910 = 0.05863 -0.01703 -0.01551 0.02167 C19 1 0.435813 0.924887 0.822146 11.00000 0.10383 0.07463 = 0.08753 -0.02552 -0.02514 0.00798 C20 1 0.410437 0.902603 0.754793 11.00000 0.08888 0.06325 = 0.06982 -0.00370 -0.00957 0.01003 C21 1 0.201768 0.565367 0.477315 11.00000 0.04435 0.04271 = 0.05087 -0.00128 0.00309 -0.00354 C22 1 0.143090 0.501603 0.466352 11.00000 0.05017 0.05961 = 0.06401 -0.00406 0.01056 -0.00992 C23 1 0.093612 0.454817 0.457608 11.00000 0.06613 0.09245 = 0.09408 -0.00705 0.01053 -0.03361 C24 1 0.258227 0.446971 0.408989 11.00000 0.04283 0.04117 = 0.04882 -0.00374 0.00145 -0.00726 C25 1 0.233393 0.444381 0.339921 11.00000 0.05551 0.03813 = 0.05522 0.00006 -0.00531 -0.00414 C26 1 0.226679 0.355644 0.306323 11.00000 0.06233 0.04861 = 0.04645 -0.00346 -0.00828 -0.00988 C27 1 0.243347 0.269232 0.340360 11.00000 0.06316 0.03967 = 0.05224 -0.00480 0.00432 -0.01334 C28 1 0.270945 0.273724 0.408504 11.00000 0.07299 0.04052 = 0.05265 0.00165 0.00141 -0.00265 C29 1 0.278629 0.362633 0.442504 11.00000 0.06103 0.05012 = 0.04559 -0.00122 -0.00028 -0.00372 C30 1 0.242354 0.097192 0.338722 11.00000 0.12142 0.04052 = 0.07079 -0.00738 0.00647 -0.00616 H1 2 0.416473 0.818123 0.425214 11.00000 0.09508 H1A 2 0.341037 0.732486 0.539890 11.00000 0.06324 H2 2 0.458597 0.812929 0.313160 11.00000 0.09267 H3 2 0.559015 0.714851 0.318236 11.00000 0.10676 H4 2 0.577241 0.653089 0.438855 11.00000 0.13207 H5 2 0.491614 0.716049 0.507912 11.00000 0.11275 H7 2 0.331715 0.640505 0.312952 11.00000 0.06894 H8 2 0.430202 0.564626 0.255387 11.00000 0.07971 H9 2 0.500471 0.474162 0.350786 11.00000 0.07239 H10 2 0.443669 0.486894 0.460186 11.00000 0.06509 H11 2 0.301298 0.666850 0.443908 11.00000 0.03148 H13A 2 0.429617 0.682574 0.637577 11.00000 0.09991 H13B 2 0.360884 0.639003 0.662047 11.00000 0.12664 H14A 2 0.380807 0.839026 0.627152 11.00000 0.11812 H14B 2 0.315554 0.784500 0.658744 11.00000 0.10188 H16 2 0.392928 0.669270 0.777678 11.00000 0.08536 H17 2 0.433423 0.708463 0.886842 11.00000 0.10466 H18 2 0.467205 0.871720 0.918422 11.00000 0.11173 H19 2 0.442961 0.995099 0.832938 11.00000 0.11877 H20 2 0.406071 0.950055 0.719430 11.00000 0.08024 H23 2 0.057383 0.415122 0.449764 11.00000 0.11212 H25 2 0.220774 0.504830 0.316144 11.00000 0.07183 H28 2 0.285410 0.216763 0.432778 11.00000 0.07490 H29 2 0.295947 0.365594 0.493419 11.00000 0.07129 H30A 2 0.230699 0.049445 0.307494 11.00000 0.07154 H30B 2 0.288407 0.087836 0.356206 11.00000 0.08591 H30C 2 0.216642 0.094946 0.382474 11.00000 0.11358 HKLF 4 REM l11_a.res in C2/c REM wR2 = 0.1090, GooF = S = 1.082, Restrained GooF = 1.082 for all data REM R1 = 0.0402 for 4046 Fo > 4sig(Fo) and 0.0513 for all 4711 data REM 443 parameters refined using 1 restraints END WGHT 0.0416 8.4363 REM Highest difference peak 0.374, deepest hole -0.442, 1-sigma level 0.048 Q1 1 0.1579 0.3310 0.2464 11.00000 0.05 0.37 Q2 1 0.3463 0.7223 0.6673 11.00000 0.05 0.23 Q3 1 0.4526 0.7644 0.3789 11.00000 0.05 0.18 Q4 1 0.2373 0.3959 0.3208 11.00000 0.05 0.17 Q5 1 0.2369 0.3163 0.3196 11.00000 0.05 0.17 Q6 1 0.2006 0.2594 0.2404 11.00000 0.05 0.16 Q7 1 0.2570 0.4019 0.4248 11.00000 0.05 0.16 Q8 1 0.4139 0.5813 0.4167 11.00000 0.05 0.16 Q9 1 0.3915 0.5368 0.4202 11.00000 0.05 0.16 Q10 1 0.4449 0.5008 0.3813 11.00000 0.05 0.16 Q11 1 0.2843 0.3208 0.4209 11.00000 0.05 0.16 Q12 1 0.4713 0.8044 0.3873 11.00000 0.05 0.15 Q13 1 0.3581 0.5926 0.4232 11.00000 0.05 0.15 Q14 1 0.5179 0.7802 0.3551 11.00000 0.05 0.15 Q15 1 0.4574 0.5378 0.3978 11.00000 0.05 0.15 ; _shelx_res_checksum 90743 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 0.45524(2) 0.64866(3) 0.38376(2) 0.04331(14) Uani 1 1 d . . . . . Cl1 Cl 0.19569(6) 0.35268(7) 0.21968(5) 0.0880(3) Uani 1 1 d . . . . . O1 O 0.35993(13) 0.51970(16) 0.55979(11) 0.0663(6) Uani 1 1 d . . . . . O2 O 0.19915(10) 0.64035(15) 0.51114(11) 0.0574(5) Uani 1 1 d . . . . . O3 O 0.23238(13) 0.18655(15) 0.30324(11) 0.0672(6) Uani 1 1 d . . . . . N1 N 0.35649(14) 0.6831(2) 0.56224(13) 0.0555(6) Uani 1 1 d . . . . . N2 N 0.25760(11) 0.53736(16) 0.44633(11) 0.0434(5) Uani 1 1 d . . . . . C1 C 0.45266(19) 0.7873(3) 0.4176(2) 0.0720(11) Uani 1 1 d . . . . . C2 C 0.47886(19) 0.7855(3) 0.3533(2) 0.0658(9) Uani 1 1 d . . . . . C3 C 0.53682(19) 0.7289(3) 0.3578(2) 0.0768(11) Uani 1 1 d . . . . . C4 C 0.5471(2) 0.6946(3) 0.4254(3) 0.0879(14) Uani 1 1 d . . . . . C5 C 0.4948(3) 0.7319(4) 0.4626(2) 0.0874(14) Uani 1 1 d D . . . . C6 C 0.36978(13) 0.57462(19) 0.40538(13) 0.0416(6) Uani 1 1 d . . . . . C7 C 0.36674(15) 0.6011(2) 0.33404(14) 0.0484(6) Uani 1 1 d . . . . . C8 C 0.42264(17) 0.5587(2) 0.30397(17) 0.0600(8) Uani 1 1 d . . . . . C9 C 0.46040(17) 0.5062(2) 0.35566(19) 0.0624(8) Uani 1 1 d . . . . . C10 C 0.42849(15) 0.5150(2) 0.41845(17) 0.0503(7) Uani 1 1 d . . . . . C11 C 0.31808(13) 0.6018(2) 0.45513(13) 0.0414(6) Uani 1 1 d . . . . . C12 C 0.34690(13) 0.5971(2) 0.53149(14) 0.0470(6) Uani 1 1 d . . . . . C13 C 0.3816(2) 0.6915(3) 0.63538(18) 0.0677(9) Uani 1 1 d . . . . . C14 C 0.3649(3) 0.7876(3) 0.66336(19) 0.0753(11) Uani 1 1 d . . . . . C15 C 0.39398(17) 0.8087(3) 0.73642(15) 0.0603(8) Uani 1 1 d . . . . . C16 C 0.4035(2) 0.7368(3) 0.78670(18) 0.0708(9) Uani 1 1 d . . . . . C17 C 0.4290(2) 0.7602(3) 0.85324(19) 0.0772(10) Uani 1 1 d . . . . . C18 C 0.4448(2) 0.8534(4) 0.8705(2) 0.0853(12) Uani 1 1 d . . . . . C19 C 0.4358(2) 0.9249(4) 0.8221(2) 0.0903(13) Uani 1 1 d . . . . . C20 C 0.4104(2) 0.9026(3) 0.7548(2) 0.0747(10) Uani 1 1 d . . . . . C21 C 0.20177(14) 0.5654(2) 0.47732(14) 0.0460(6) Uani 1 1 d . . . . . C22 C 0.14309(15) 0.5016(2) 0.46635(17) 0.0576(7) Uani 1 1 d . . . . . C23 C 0.0936(2) 0.4548(3) 0.4576(2) 0.0840(12) Uani 1 1 d . . . . . C24 C 0.25823(13) 0.44697(19) 0.40899(14) 0.0444(6) Uani 1 1 d . . . . . C25 C 0.23339(15) 0.4444(2) 0.33992(15) 0.0501(7) Uani 1 1 d . . . . . C26 C 0.22668(16) 0.3556(2) 0.30632(15) 0.0531(7) Uani 1 1 d . . . . . C27 C 0.24335(15) 0.2692(2) 0.34036(15) 0.0517(7) Uani 1 1 d . . . . . C28 C 0.27095(17) 0.2737(2) 0.40850(16) 0.0555(7) Uani 1 1 d . . . . . C29 C 0.27863(16) 0.3626(2) 0.44250(15) 0.0525(7) Uani 1 1 d . . . . . C30 C 0.2424(3) 0.0972(3) 0.3387(2) 0.0776(11) Uani 1 1 d . . . . . H1 H 0.416(2) 0.818(3) 0.425(2) 0.095(14) Uiso 1 1 d . . . . . H1A H 0.3410(17) 0.732(3) 0.5399(17) 0.063(10) Uiso 1 1 d . . . . . H2 H 0.459(2) 0.813(3) 0.313(2) 0.093(13) Uiso 1 1 d . . . . . H3 H 0.559(2) 0.715(3) 0.318(2) 0.107(15) Uiso 1 1 d . . . . . H4 H 0.577(3) 0.653(4) 0.439(3) 0.13(2) Uiso 1 1 d . . . . . H5 H 0.492(2) 0.716(3) 0.5079(12) 0.113(16) Uiso 1 1 d D . . . . H7 H 0.3317(18) 0.641(2) 0.3130(18) 0.069(10) Uiso 1 1 d . . . . . H8 H 0.4302(18) 0.565(3) 0.255(2) 0.080(11) Uiso 1 1 d . . . . . H9 H 0.5005(18) 0.474(3) 0.3508(17) 0.072(11) Uiso 1 1 d . . . . . H10 H 0.4437(16) 0.487(3) 0.4602(17) 0.065(10) Uiso 1 1 d . . . . . H11 H 0.3013(12) 0.6669(19) 0.4439(12) 0.031(6) Uiso 1 1 d . . . . . H13A H 0.430(2) 0.683(3) 0.638(2) 0.100(14) Uiso 1 1 d . . . . . H13B H 0.361(3) 0.639(4) 0.662(3) 0.127(19) Uiso 1 1 d . . . . . H14A H 0.381(2) 0.839(3) 0.627(3) 0.118(17) Uiso 1 1 d . . . . . H14B H 0.316(2) 0.784(3) 0.659(2) 0.102(15) Uiso 1 1 d . . . . . H16 H 0.393(2) 0.669(3) 0.778(2) 0.085(12) Uiso 1 1 d . . . . . H17 H 0.433(2) 0.708(3) 0.887(2) 0.105(15) Uiso 1 1 d . . . . . H18 H 0.467(2) 0.872(3) 0.918(2) 0.112(15) Uiso 1 1 d . . . . . H19 H 0.443(2) 0.995(4) 0.833(2) 0.119(16) Uiso 1 1 d . . . . . H20 H 0.4061(18) 0.950(3) 0.7194(19) 0.080(12) Uiso 1 1 d . . . . . H23 H 0.057(2) 0.415(3) 0.450(2) 0.112(16) Uiso 1 1 d . . . . . H25 H 0.2208(17) 0.505(3) 0.3161(18) 0.072(10) Uiso 1 1 d . . . . . H28 H 0.2854(18) 0.217(3) 0.4328(18) 0.075(11) Uiso 1 1 d . . . . . H29 H 0.2959(18) 0.366(2) 0.4934(19) 0.071(10) Uiso 1 1 d . . . . . H30A H 0.2307(18) 0.049(3) 0.3075(19) 0.072(10) Uiso 1 1 d . . . . . H30B H 0.288(2) 0.088(3) 0.356(2) 0.086(14) Uiso 1 1 d . . . . . H30C H 0.217(2) 0.095(3) 0.382(3) 0.114(16) 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 Fe1 0.0383(2) 0.0424(3) 0.0490(3) 0.00171(18) 0.00183(16) -0.00252(17) Cl1 0.1365(9) 0.0605(5) 0.0604(5) -0.0055(4) -0.0358(5) -0.0125(5) O1 0.0934(17) 0.0502(13) 0.0531(12) 0.0060(10) -0.0094(11) -0.0036(11) O2 0.0512(11) 0.0527(13) 0.0692(13) -0.0122(10) 0.0110(10) -0.0022(9) O3 0.1008(18) 0.0391(11) 0.0606(13) -0.0085(9) -0.0009(12) -0.0111(11) N1 0.0623(16) 0.0516(15) 0.0507(14) -0.0097(12) -0.0087(11) 0.0015(12) N2 0.0414(11) 0.0371(12) 0.0513(13) -0.0070(9) 0.0017(9) -0.0067(9) C1 0.0522(19) 0.058(2) 0.108(3) -0.031(2) 0.019(2) -0.0126(16) C2 0.072(2) 0.0490(19) 0.076(2) 0.0067(16) -0.0016(18) -0.0106(16) C3 0.064(2) 0.068(2) 0.102(3) -0.013(2) 0.033(2) -0.0208(18) C4 0.051(2) 0.073(3) 0.134(4) 0.018(3) -0.028(2) -0.0124(19) C5 0.104(3) 0.104(3) 0.053(2) -0.006(2) -0.005(2) -0.060(3) C6 0.0410(13) 0.0355(14) 0.0475(14) -0.0002(11) -0.0011(11) -0.0044(10) C7 0.0501(16) 0.0486(17) 0.0455(15) 0.0005(12) -0.0039(12) -0.0096(13) C8 0.069(2) 0.059(2) 0.0526(18) -0.0114(15) 0.0128(15) -0.0131(16) C9 0.0549(18) 0.0500(19) 0.084(2) -0.0086(16) 0.0171(17) 0.0068(14) C10 0.0511(16) 0.0346(15) 0.0646(19) 0.0083(13) 0.0013(14) 0.0024(12) C11 0.0407(13) 0.0356(14) 0.0475(14) -0.0028(11) 0.0000(11) -0.0056(11) C12 0.0436(14) 0.0491(17) 0.0481(15) -0.0057(13) 0.0012(11) -0.0046(12) C13 0.075(2) 0.072(2) 0.0534(18) -0.0163(17) -0.0160(17) 0.0105(19) C14 0.096(3) 0.073(3) 0.0535(19) -0.0151(17) -0.0152(19) 0.017(2) C15 0.0648(19) 0.069(2) 0.0466(16) -0.0091(15) -0.0034(14) 0.0115(16) C16 0.086(3) 0.069(2) 0.0553(19) -0.0015(17) -0.0058(17) 0.0054(19) C17 0.087(3) 0.089(3) 0.053(2) -0.0022(19) -0.0050(18) 0.008(2) C18 0.095(3) 0.099(3) 0.059(2) -0.017(2) -0.016(2) 0.022(2) C19 0.104(3) 0.075(3) 0.088(3) -0.026(2) -0.025(2) 0.008(2) C20 0.089(3) 0.063(2) 0.070(2) -0.0037(18) -0.0096(19) 0.0100(19) C21 0.0443(14) 0.0427(15) 0.0509(15) -0.0013(12) 0.0031(12) -0.0035(11) C22 0.0502(17) 0.0596(19) 0.0640(19) -0.0041(15) 0.0106(14) -0.0099(14) C23 0.066(2) 0.092(3) 0.094(3) -0.007(2) 0.011(2) -0.034(2) C24 0.0428(14) 0.0412(15) 0.0488(15) -0.0037(11) 0.0015(11) -0.0073(11) C25 0.0555(16) 0.0381(15) 0.0552(17) 0.0001(12) -0.0053(13) -0.0041(12) C26 0.0623(17) 0.0486(17) 0.0465(15) -0.0035(12) -0.0083(13) -0.0099(13) C27 0.0632(18) 0.0397(15) 0.0522(16) -0.0048(12) 0.0043(13) -0.0133(13) C28 0.073(2) 0.0405(17) 0.0526(17) 0.0016(13) 0.0014(14) -0.0026(14) C29 0.0610(18) 0.0501(17) 0.0456(16) -0.0012(13) -0.0003(13) -0.0037(13) C30 0.121(4) 0.041(2) 0.071(2) -0.0074(17) 0.006(2) -0.006(2) 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' 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 C5 Fe1 C1 40.21(18) . . ? C5 Fe1 C4 40.4(2) . . ? C1 Fe1 C4 67.71(18) . . ? C5 Fe1 C2 66.93(17) . . ? C1 Fe1 C2 39.77(16) . . ? C4 Fe1 C2 67.00(17) . . ? C5 Fe1 C7 144.00(18) . . ? C1 Fe1 C7 114.47(15) . . ? C4 Fe1 C7 175.06(19) . . ? C2 Fe1 C7 111.55(14) . . ? C5 Fe1 C9 136.32(19) . . ? C1 Fe1 C9 176.40(18) . . ? C4 Fe1 C9 110.13(17) . . ? C2 Fe1 C9 142.66(15) . . ? C7 Fe1 C9 67.92(13) . . ? C5 Fe1 C10 111.11(15) . . ? C1 Fe1 C10 137.12(15) . . ? C4 Fe1 C10 113.36(16) . . ? C2 Fe1 C10 176.78(14) . . ? C7 Fe1 C10 68.38(12) . . ? C9 Fe1 C10 40.51(13) . . ? C5 Fe1 C6 114.20(14) . . ? C1 Fe1 C6 111.40(13) . . ? C4 Fe1 C6 143.41(17) . . ? C2 Fe1 C6 136.97(13) . . ? C7 Fe1 C6 40.79(10) . . ? C9 Fe1 C6 68.44(12) . . ? C10 Fe1 C6 40.95(11) . . ? C5 Fe1 C8 175.3(2) . . ? C1 Fe1 C8 143.36(17) . . ? C4 Fe1 C8 135.23(19) . . ? C2 Fe1 C8 114.11(15) . . ? C7 Fe1 C8 40.45(13) . . ? C9 Fe1 C8 40.17(14) . . ? C10 Fe1 C8 68.07(13) . . ? C6 Fe1 C8 68.43(12) . . ? C5 Fe1 C3 66.99(17) . . ? C1 Fe1 C3 66.92(15) . . ? C4 Fe1 C3 39.80(18) . . ? C2 Fe1 C3 39.56(16) . . ? C7 Fe1 C3 136.17(16) . . ? C9 Fe1 C3 113.47(15) . . ? C10 Fe1 C3 142.62(15) . . ? C6 Fe1 C3 176.12(16) . . ? C8 Fe1 C3 110.65(15) . . ? C27 O3 C30 117.6(3) . . ? C12 N1 C13 121.8(3) . . ? C12 N1 H1A 117(2) . . ? C13 N1 H1A 121(2) . . ? C21 N2 C24 120.5(2) . . ? C21 N2 C11 117.0(2) . . ? C24 N2 C11 122.4(2) . . ? C2 C1 C5 107.8(4) . . ? C2 C1 Fe1 70.9(2) . . ? C5 C1 Fe1 69.8(2) . . ? C2 C1 H1 123(3) . . ? C5 C1 H1 130(3) . . ? Fe1 C1 H1 125(3) . . ? C1 C2 C3 108.5(4) . . ? C1 C2 Fe1 69.4(2) . . ? C3 C2 Fe1 70.6(2) . . ? C1 C2 H2 125(3) . . ? C3 C2 H2 126(3) . . ? Fe1 C2 H2 122(3) . . ? C2 C3 C4 108.3(4) . . ? C2 C3 Fe1 69.9(2) . . ? C4 C3 Fe1 69.5(2) . . ? C2 C3 H3 120(3) . . ? C4 C3 H3 131(3) . . ? Fe1 C3 H3 121(3) . . ? C3 C4 C5 107.2(4) . . ? C3 C4 Fe1 70.7(2) . . ? C5 C4 Fe1 69.2(2) . . ? C3 C4 H4 124(4) . . ? C5 C4 H4 128(4) . . ? Fe1 C4 H4 120(4) . . ? C1 C5 C4 108.2(4) . . ? C1 C5 Fe1 70.0(2) . . ? C4 C5 Fe1 70.4(2) . . ? C1 C5 H5 131(3) . . ? C4 C5 H5 121(3) . . ? Fe1 C5 H5 123(3) . . ? C7 C6 C10 107.1(3) . . ? C7 C6 C11 125.0(2) . . ? C10 C6 C11 127.8(2) . . ? C7 C6 Fe1 69.52(15) . . ? C10 C6 Fe1 69.50(15) . . ? C11 C6 Fe1 128.21(18) . . ? C8 C7 C6 108.3(3) . . ? C8 C7 Fe1 69.93(18) . . ? C6 C7 Fe1 69.69(15) . . ? C8 C7 H7 129(2) . . ? C6 C7 H7 123(2) . . ? Fe1 C7 H7 126(2) . . ? C9 C8 C7 108.2(3) . . ? C9 C8 Fe1 69.78(19) . . ? C7 C8 Fe1 69.62(17) . . ? C9 C8 H8 129(2) . . ? C7 C8 H8 123(2) . . ? Fe1 C8 H8 128(2) . . ? C8 C9 C10 108.6(3) . . ? C8 C9 Fe1 70.05(19) . . ? C10 C9 Fe1 69.79(17) . . ? C8 C9 H9 126(2) . . ? C10 C9 H9 125(2) . . ? Fe1 C9 H9 123(2) . . ? C9 C10 C6 107.8(3) . . ? C9 C10 Fe1 69.71(18) . . ? C6 C10 Fe1 69.55(15) . . ? C9 C10 H10 125(2) . . ? C6 C10 H10 127(2) . . ? Fe1 C10 H10 126(2) . . ? N2 C11 C6 110.9(2) . . ? N2 C11 C12 108.7(2) . . ? C6 C11 C12 112.4(2) . . ? N2 C11 H11 105.4(15) . . ? C6 C11 H11 108.9(14) . . ? C12 C11 H11 110.3(14) . . ? O1 C12 N1 124.0(3) . . ? O1 C12 C11 121.2(2) . . ? N1 C12 C11 114.8(3) . . ? N1 C13 C14 110.8(3) . . ? N1 C13 H13A 107(3) . . ? C14 C13 H13A 110(3) . . ? N1 C13 H13B 109(3) . . ? C14 C13 H13B 111(3) . . ? H13A C13 H13B 109(4) . . ? C13 C14 C15 115.8(3) . . ? C13 C14 H14A 106(3) . . ? C15 C14 H14A 112(3) . . ? C13 C14 H14B 100(3) . . ? C15 C14 H14B 114(3) . . ? H14A C14 H14B 108(4) . . ? C20 C15 C16 118.2(3) . . ? C20 C15 C14 119.3(3) . . ? C16 C15 C14 122.5(3) . . ? C17 C16 C15 120.3(4) . . ? C17 C16 H16 117(2) . . ? C15 C16 H16 123(2) . . ? C18 C17 C16 120.7(4) . . ? C18 C17 H17 122(3) . . ? C16 C17 H17 118(3) . . ? C17 C18 C19 120.0(4) . . ? C17 C18 H18 122(3) . . ? C19 C18 H18 118(3) . . ? C18 C19 C20 120.1(4) . . ? C18 C19 H19 123(3) . . ? C20 C19 H19 116(3) . . ? C15 C20 C19 120.7(4) . . ? C15 C20 H20 117(2) . . ? C19 C20 H20 122(2) . . ? O2 C21 N2 123.1(2) . . ? O2 C21 C22 121.4(3) . . ? N2 C21 C22 115.5(2) . . ? C23 C22 C21 176.2(4) . . ? C22 C23 H23 176(3) . . ? C29 C24 C25 120.1(3) . . ? C29 C24 N2 120.5(2) . . ? C25 C24 N2 119.2(2) . . ? C26 C25 C24 119.2(3) . . ? C26 C25 H25 121(2) . . ? C24 C25 H25 119(2) . . ? C25 C26 C27 121.6(3) . . ? C25 C26 Cl1 119.1(2) . . ? C27 C26 Cl1 119.3(2) . . ? O3 C27 C26 116.6(3) . . ? O3 C27 C28 125.1(3) . . ? C26 C27 C28 118.3(3) . . ? C27 C28 C29 120.5(3) . . ? C27 C28 H28 121(2) . . ? C29 C28 H28 118(2) . . ? C24 C29 C28 120.2(3) . . ? C24 C29 H29 119.1(19) . . ? C28 C29 H29 120.5(19) . . ? O3 C30 H30A 107(2) . . ? O3 C30 H30B 113(3) . . ? H30A C30 H30B 109(3) . . ? O3 C30 H30C 112(3) . . ? H30A C30 H30C 114(3) . . ? H30B C30 H30C 103(3) . . ? 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 C5 2.015(4) . ? Fe1 C1 2.018(4) . ? Fe1 C4 2.029(4) . ? Fe1 C2 2.037(3) . ? Fe1 C7 2.038(3) . ? Fe1 C9 2.039(3) . ? Fe1 C10 2.040(3) . ? Fe1 C6 2.041(3) . ? Fe1 C8 2.042(3) . ? Fe1 C3 2.045(3) . ? Cl1 C26 1.738(3) . ? O1 C12 1.215(3) . ? O2 C21 1.224(3) . ? O3 C27 1.353(3) . ? O3 C30 1.414(4) . ? N1 C12 1.331(4) . ? N1 C13 1.466(4) . ? N1 H1A 0.85(3) . ? N2 C21 1.349(3) . ? N2 C24 1.438(3) . ? N2 C11 1.487(3) . ? C1 C2 1.379(5) . ? C1 C5 1.386(6) . ? C1 H1 0.85(4) . ? C2 C3 1.382(5) . ? C2 H2 0.93(4) . ? C3 C4 1.387(6) . ? C3 H3 0.93(4) . ? C4 C5 1.397(7) . ? C4 H4 0.85(5) . ? C5 H5 0.909(19) . ? C6 C7 1.421(4) . ? C6 C10 1.427(4) . ? C6 C11 1.500(4) . ? C7 C8 1.411(4) . ? C7 H7 0.95(3) . ? C8 C9 1.402(5) . ? C8 H8 0.96(4) . ? C9 C10 1.412(5) . ? C9 H9 0.92(4) . ? C10 H10 0.92(3) . ? C11 C12 1.542(4) . ? C11 H11 0.97(3) . ? C13 C14 1.474(5) . ? C13 H13A 0.95(5) . ? C13 H13B 0.99(5) . ? C14 C15 1.511(4) . ? C14 H14A 1.06(5) . ? C14 H14B 0.97(5) . ? C15 C20 1.372(5) . ? C15 C16 1.389(5) . ? C16 C17 1.383(5) . ? C16 H16 0.97(4) . ? C17 C18 1.355(6) . ? C17 H17 0.96(4) . ? C18 C19 1.359(6) . ? C18 H18 1.03(5) . ? C19 C20 1.392(5) . ? C19 H19 1.00(5) . ? C20 H20 0.94(4) . ? C21 C22 1.456(4) . ? C22 C23 1.172(5) . ? C23 H23 0.90(5) . ? C24 C29 1.374(4) . ? C24 C25 1.386(4) . ? C25 C26 1.384(4) . ? C25 H25 0.97(4) . ? C26 C27 1.386(4) . ? C27 C28 1.387(4) . ? C28 C29 1.391(4) . ? C28 H28 0.95(4) . ? C29 H29 1.02(4) . ? C30 H30A 0.91(4) . ? C30 H30B 0.96(4) . ? C30 H30C 1.02(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 _geom_hbond_publ_flag N1 H1A O2 0.85(3) 2.13(4) 2.981(4) 177(3) 7_566 yes 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 C5 C1 C2 C3 0.3(4) . . . . ? Fe1 C1 C2 C3 -59.9(3) . . . . ? C5 C1 C2 Fe1 60.3(3) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? Fe1 C2 C3 C4 -59.0(3) . . . . ? C1 C2 C3 Fe1 59.2(2) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? Fe1 C3 C4 C5 -59.9(3) . . . . ? C2 C3 C4 Fe1 59.3(3) . . . . ? C2 C1 C5 C4 -0.7(4) . . . . ? Fe1 C1 C5 C4 60.2(3) . . . . ? C2 C1 C5 Fe1 -61.0(2) . . . . ? C3 C4 C5 C1 0.8(4) . . . . ? Fe1 C4 C5 C1 -60.0(3) . . . . ? C3 C4 C5 Fe1 60.9(3) . . . . ? C10 C6 C7 C8 -0.1(3) . . . . ? C11 C6 C7 C8 -177.5(2) . . . . ? Fe1 C6 C7 C8 59.5(2) . . . . ? C10 C6 C7 Fe1 -59.59(19) . . . . ? C11 C6 C7 Fe1 123.0(3) . . . . ? C6 C7 C8 C9 0.0(3) . . . . ? Fe1 C7 C8 C9 59.3(2) . . . . ? C6 C7 C8 Fe1 -59.33(19) . . . . ? C7 C8 C9 C10 0.1(4) . . . . ? Fe1 C8 C9 C10 59.3(2) . . . . ? C7 C8 C9 Fe1 -59.2(2) . . . . ? C8 C9 C10 C6 -0.2(4) . . . . ? Fe1 C9 C10 C6 59.3(2) . . . . ? C8 C9 C10 Fe1 -59.5(2) . . . . ? C7 C6 C10 C9 0.2(3) . . . . ? C11 C6 C10 C9 177.5(3) . . . . ? Fe1 C6 C10 C9 -59.4(2) . . . . ? C7 C6 C10 Fe1 59.60(19) . . . . ? C11 C6 C10 Fe1 -123.1(3) . . . . ? C21 N2 C11 C6 -166.9(2) . . . . ? C24 N2 C11 C6 15.5(3) . . . . ? C21 N2 C11 C12 69.1(3) . . . . ? C24 N2 C11 C12 -108.5(3) . . . . ? C7 C6 C11 N2 79.6(3) . . . . ? C10 C6 C11 N2 -97.3(3) . . . . ? Fe1 C6 C11 N2 170.04(17) . . . . ? C7 C6 C11 C12 -158.5(3) . . . . ? C10 C6 C11 C12 24.6(4) . . . . ? Fe1 C6 C11 C12 -68.1(3) . . . . ? C13 N1 C12 O1 -2.6(5) . . . . ? C13 N1 C12 C11 178.1(3) . . . . ? N2 C11 C12 O1 52.3(3) . . . . ? C6 C11 C12 O1 -70.8(3) . . . . ? N2 C11 C12 N1 -128.3(3) . . . . ? C6 C11 C12 N1 108.5(3) . . . . ? C12 N1 C13 C14 -159.7(4) . . . . ? N1 C13 C14 C15 -174.4(4) . . . . ? C13 C14 C15 C20 148.7(4) . . . . ? C13 C14 C15 C16 -32.7(6) . . . . ? C20 C15 C16 C17 -0.2(6) . . . . ? C14 C15 C16 C17 -178.8(4) . . . . ? C15 C16 C17 C18 0.4(6) . . . . ? C16 C17 C18 C19 -0.3(7) . . . . ? C17 C18 C19 C20 0.0(7) . . . . ? C16 C15 C20 C19 -0.1(6) . . . . ? C14 C15 C20 C19 178.5(4) . . . . ? C18 C19 C20 C15 0.2(7) . . . . ? C24 N2 C21 O2 178.1(3) . . . . ? C11 N2 C21 O2 0.5(4) . . . . ? C24 N2 C21 C22 -3.6(4) . . . . ? C11 N2 C21 C22 178.7(2) . . . . ? C21 N2 C24 C29 -89.7(3) . . . . ? C11 N2 C24 C29 87.8(3) . . . . ? C21 N2 C24 C25 85.7(3) . . . . ? C11 N2 C24 C25 -96.8(3) . . . . ? C29 C24 C25 C26 2.8(4) . . . . ? N2 C24 C25 C26 -172.6(3) . . . . ? C24 C25 C26 C27 0.9(5) . . . . ? C24 C25 C26 Cl1 -179.9(2) . . . . ? C30 O3 C27 C26 -173.7(4) . . . . ? C30 O3 C27 C28 7.7(5) . . . . ? C25 C26 C27 O3 177.6(3) . . . . ? Cl1 C26 C27 O3 -1.7(4) . . . . ? C25 C26 C27 C28 -3.7(5) . . . . ? Cl1 C26 C27 C28 177.0(2) . . . . ? O3 C27 C28 C29 -178.5(3) . . . . ? C26 C27 C28 C29 2.9(5) . . . . ? C25 C24 C29 C28 -3.6(4) . . . . ? N2 C24 C29 C28 171.8(3) . . . . ? C27 C28 C29 C24 0.7(5) . . . . ?