#------------------------------------------------------------------------------ #$Date: 2020-06-03 04:58:42 +0300 (Wed, 03 Jun 2020) $ #$Revision: 252560 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/45/7704573.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_7704573 loop_ _publ_author_name 'Kordestani, Nazanin' 'Amiri Rudbari, Hadi' 'Bruno, Giuseppe' 'Scopelliti, Rosario' 'Braun, Jason D.' 'Herbert, David E.' 'Blacque, Olivier' 'Correia, Isabel' 'Zaman, Mohammad Al-moktadir' 'Bindu, Mortuza Mamun' 'Janiak, Christoph' 'Enamullah, Mohammed' _publ_section_title ; Solid-state to solution helicity inversion of pseudotetrahedral chiral copper(II) complexes with 2,4-dihalo-salicylaldiminate ligands ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT01649G _journal_year 2020 _chemical_absolute_configuration rmad _chemical_formula_sum 'C30 H24 Cl4 Cu N2 O2' _chemical_formula_weight 649.85 _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_method SHELXL-2016/6 _audit_update_record ; 2019-11-09 deposited with the CCDC. 2020-06-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.8710(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.6322(2) _cell_length_b 14.8439(3) _cell_length_c 11.1572(3) _cell_measurement_reflns_used 9726 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 29.59 _cell_measurement_theta_min 2.30 _cell_volume 1416.16(6) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_unetI/netI 0.0390 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 79451 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 32.581 _diffrn_reflns_theta_min 2.297 _exptl_absorpt_coefficient_mu 1.180 _exptl_absorpt_correction_T_max 0.814 _exptl_absorpt_correction_T_min 0.639 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS; Bruker, 2008' _exptl_crystal_colour 'dark black' _exptl_crystal_density_diffrn 1.524 _exptl_crystal_description prismatic _exptl_crystal_F_000 662 _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.594 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.082 _refine_ls_abs_structure_details ; Flack x determined using 3767 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.005(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 352 _refine_ls_number_reflns 10276 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.993 _refine_ls_R_factor_all 0.0378 _refine_ls_R_factor_gt 0.0288 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0434P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.0729 _reflns_Friedel_coverage 0.935 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.997 _reflns_number_gt 8716 _reflns_number_total 10276 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt01649g2.cif _cod_data_source_block shelx_CCDC5 _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 7704573 _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 HADI1901_1m_a.res in P2(1) shelx.res created by SHELXL-2016/6 at 08:54:09 on 09-Nov-2019 CELL 0.71073 8.6322 14.8439 11.1572 90.000 97.871 90.000 ZERR 2.00 0.0002 0.0003 0.0003 0.000 0.001 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O CL CU UNIT 60 48 4 4 8 2 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF LIST 6 L.S. 8 TEMP 0.00 WGHT 0.043400 FVAR 0.13191 CU1 6 0.685626 0.581743 0.569288 11.00000 0.02221 0.03107 = 0.02409 -0.00165 -0.00130 0.00260 CL1 5 0.439512 0.617399 0.169753 11.00000 0.03864 0.08380 = 0.02340 0.00149 0.00644 0.00306 CL2 5 -0.122049 0.653200 0.323522 11.00000 0.02163 0.05638 = 0.05391 0.00505 -0.00277 0.00150 N1 3 0.526336 0.623903 0.668459 11.00000 0.02839 0.02938 = 0.01982 0.00206 0.00125 0.00082 C22 1 0.958324 0.553931 0.736778 11.00000 0.02306 0.03405 = 0.02815 -0.00088 0.00032 -0.00222 CL3 5 1.032511 0.686638 0.900280 11.00000 0.04990 0.04736 = 0.05215 -0.01669 -0.01057 -0.00444 CL4 5 1.260132 0.350737 0.969194 11.00000 0.08245 0.07400 = 0.06903 0.02335 -0.02818 0.02163 O1 4 0.554780 0.599361 0.422228 11.00000 0.02278 0.04183 = 0.02369 0.00044 0.00165 0.00515 O2 4 0.864263 0.612368 0.679680 11.00000 0.02775 0.03074 = 0.03457 -0.00326 -0.00643 0.00114 N2 3 0.791439 0.473422 0.512013 11.00000 0.02654 0.03070 = 0.02783 -0.00268 0.00095 0.00056 C8 1 0.578143 0.637856 0.800087 11.00000 0.03084 0.03576 = 0.01951 0.00226 0.00139 -0.00120 AFIX 13 H8 2 0.673444 0.674417 0.806379 11.00000 -1.20000 AFIX 0 C10 1 0.624733 0.548598 0.860350 11.00000 0.03551 0.04424 = 0.03020 0.01086 0.00850 0.00596 C15 1 0.576057 0.466775 0.810474 11.00000 0.07960 0.04245 = 0.04640 0.01128 0.01303 0.00898 AFIX 43 H15 2 0.508476 0.464362 0.738082 11.00000 -1.20000 AFIX 0 C14 1 0.629433 0.387194 0.869955 11.00000 0.12510 0.04461 = 0.09225 0.02612 0.04044 0.01918 AFIX 43 H14 2 0.599558 0.331737 0.835486 11.00000 -1.20000 AFIX 0 C13 1 0.724294 0.390364 0.977365 11.00000 0.10227 0.08592 = 0.09665 0.06407 0.03877 0.05111 AFIX 43 H13 2 0.758251 0.336988 1.016002 11.00000 -1.20000 AFIX 0 C12 1 0.770803 0.471394 1.029756 11.00000 0.06834 0.10799 = 0.06584 0.05427 0.00501 0.01998 AFIX 43 H12 2 0.835326 0.472979 1.103660 11.00000 -1.20000 AFIX 0 C11 1 0.720583 0.551092 0.971340 11.00000 0.04565 0.07556 = 0.04196 0.02403 -0.00124 0.00080 AFIX 43 H11 2 0.751123 0.606219 1.006527 11.00000 -1.20000 AFIX 0 C1 1 0.380689 0.631793 0.626791 11.00000 0.02701 0.03681 = 0.02468 0.00212 0.00429 0.00022 AFIX 43 H1 2 0.312141 0.642386 0.682689 11.00000 -1.20000 AFIX 0 C2 1 0.313251 0.625708 0.500593 11.00000 0.02390 0.03305 = 0.02444 0.00139 0.00217 0.00016 C4 1 0.080039 0.641226 0.356316 11.00000 0.02084 0.03814 = 0.03759 0.00292 -0.00196 -0.00014 C5 1 0.168050 0.636141 0.260869 11.00000 0.02836 0.04597 = 0.02796 0.00209 -0.00330 -0.00018 AFIX 43 H5 2 0.120240 0.640722 0.181183 11.00000 -1.20000 AFIX 0 C6 1 0.327235 0.624200 0.286815 11.00000 0.02754 0.04103 = 0.02295 0.00091 0.00263 0.00018 C7 1 0.406821 0.614931 0.406123 11.00000 0.02401 0.02855 = 0.02518 0.00084 0.00155 0.00059 C17 1 0.980051 0.465602 0.695279 11.00000 0.02895 0.03503 = 0.03350 0.00061 -0.00351 0.00509 C16 1 0.903324 0.433848 0.579849 11.00000 0.03441 0.03174 = 0.03731 -0.00543 -0.00302 0.00641 AFIX 43 H16 2 0.938292 0.379494 0.551925 11.00000 -1.20000 AFIX 0 C23 1 0.721919 0.431426 0.396542 11.00000 0.03158 0.03224 = 0.02798 -0.00437 -0.00008 -0.00062 AFIX 13 H23 2 0.701409 0.480240 0.337357 11.00000 -1.20000 AFIX 0 C25 1 0.564115 0.390610 0.412063 11.00000 0.03232 0.02884 = 0.03921 -0.00754 0.00073 0.00002 C26 1 0.445404 0.391168 0.314783 11.00000 0.03865 0.04734 = 0.04586 -0.00678 -0.00676 -0.00047 AFIX 43 H26 2 0.462399 0.417439 0.242040 11.00000 -1.20000 AFIX 0 C27 1 0.300781 0.352556 0.325494 11.00000 0.03414 0.05746 = 0.07406 -0.01327 -0.01000 -0.00269 AFIX 43 H27 2 0.222209 0.352571 0.259535 11.00000 -1.20000 AFIX 0 C28 1 0.273327 0.314159 0.433755 11.00000 0.03730 0.04402 = 0.08987 -0.01178 0.01001 -0.00636 AFIX 43 H28 2 0.176238 0.289300 0.441285 11.00000 -1.20000 AFIX 0 C29 1 0.391336 0.313235 0.529962 11.00000 0.05125 0.04257 = 0.06741 -0.00249 0.01856 -0.01090 AFIX 43 H29 2 0.374170 0.287276 0.602857 11.00000 -1.20000 AFIX 0 C30 1 0.535788 0.350782 0.518931 11.00000 0.04118 0.03703 = 0.04420 -0.00183 0.00513 -0.00443 AFIX 43 H30 2 0.614885 0.349143 0.584481 11.00000 -1.20000 AFIX 0 C24 1 0.827398 0.363885 0.343925 11.00000 0.03938 0.04745 = 0.03964 -0.01239 0.00579 0.00129 AFIX 33 H24A 2 0.773872 0.339972 0.269636 11.00000 -1.50000 H24B 2 0.921564 0.393463 0.328476 11.00000 -1.50000 H24C 2 0.853164 0.315697 0.400538 11.00000 -1.50000 AFIX 0 C18 1 1.076674 0.403935 0.765983 11.00000 0.04058 0.03814 = 0.04613 0.00240 -0.00767 0.00982 AFIX 43 H18 2 1.089232 0.345879 0.737492 11.00000 -1.20000 AFIX 0 C19 1 1.152541 0.429346 0.877094 11.00000 0.03947 0.04898 = 0.04312 0.01238 -0.00723 0.00644 C20 1 1.142715 0.516629 0.917485 11.00000 0.03504 0.05784 = 0.03203 0.00268 -0.00907 -0.00300 AFIX 43 H20 2 1.198879 0.534340 0.990815 11.00000 -1.20000 AFIX 0 C21 1 1.049209 0.577091 0.848365 11.00000 0.02834 0.04127 = 0.03076 -0.00213 -0.00383 -0.00361 C9 1 0.463488 0.689146 0.867324 11.00000 0.04528 0.04498 = 0.02683 -0.00415 0.00425 0.00570 AFIX 33 H9A 2 0.506356 0.694911 0.951019 11.00000 -1.50000 H9B 2 0.445584 0.747955 0.832362 11.00000 -1.50000 H9C 2 0.366341 0.656860 0.860919 11.00000 -1.50000 AFIX 0 C3 1 0.149985 0.636977 0.473838 11.00000 0.02222 0.03855 = 0.03169 0.00076 0.00431 -0.00123 AFIX 43 H3 2 0.089516 0.641546 0.536447 11.00000 -1.20000 AFIX 0 HKLF 4 REM HADI1901_1m_a.res in P2(1) REM R1 = 0.0288 for 8716 Fo > 4sig(Fo) and 0.0378 for all 10276 data REM 352 parameters refined using 1 restraints END WGHT 0.0434 0.0000 REM Highest difference peak 0.594, deepest hole -0.352, 1-sigma level 0.082 Q1 1 0.6775 0.5828 0.5014 11.00000 0.05 0.59 Q2 1 0.6917 0.5831 0.6386 11.00000 0.05 0.52 Q3 1 -0.0978 0.6536 0.2632 11.00000 0.05 0.37 Q4 1 0.1277 0.6405 0.4052 11.00000 0.05 0.37 Q5 1 1.0148 0.5767 0.7812 11.00000 0.05 0.35 Q6 1 -0.1054 0.6528 0.3950 11.00000 0.05 0.35 Q7 1 0.3420 0.6245 0.5605 11.00000 0.05 0.35 Q8 1 1.0373 0.6928 0.8376 11.00000 0.05 0.33 Q9 1 1.2918 0.3493 0.9034 11.00000 0.05 0.33 Q10 1 0.1200 0.6397 0.3080 11.00000 0.05 0.32 Q11 1 0.2516 0.6311 0.2807 11.00000 0.05 0.31 Q12 1 0.4459 0.6163 0.2379 11.00000 0.05 0.30 Q13 1 0.3540 0.6190 0.3508 11.00000 0.05 0.30 Q14 1 0.9516 0.4476 0.6380 11.00000 0.05 0.29 Q15 1 0.7437 0.3894 1.0070 11.00000 0.05 0.29 Q16 1 0.3608 0.6178 0.2411 11.00000 0.05 0.28 Q17 1 -0.1566 0.6581 0.2949 11.00000 0.05 0.28 Q18 1 0.3571 0.6165 0.4425 11.00000 0.05 0.27 Q19 1 1.2806 0.3412 0.9964 11.00000 0.05 0.27 Q20 1 1.1082 0.4160 0.8203 11.00000 0.05 0.26 ; _shelx_res_checksum 84290 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 Cu1 Cu 0.68563(3) 0.58174(2) 0.56929(2) 0.02621(6) Uani 1 1 d . . . . . Cl1 Cl 0.43951(7) 0.61740(6) 0.16975(5) 0.04841(17) Uani 1 1 d . . . . . Cl2 Cl -0.12205(7) 0.65320(5) 0.32352(6) 0.04471(15) Uani 1 1 d . . . . . N1 N 0.5263(2) 0.62390(13) 0.66846(14) 0.0261(3) Uani 1 1 d . . . . . C22 C 0.9583(2) 0.55393(15) 0.73678(19) 0.0287(4) Uani 1 1 d . . . . . Cl3 Cl 1.03251(9) 0.68664(5) 0.90028(7) 0.05144(17) Uani 1 1 d . . . . . Cl4 Cl 1.26013(13) 0.35074(7) 0.96919(9) 0.0787(3) Uani 1 1 d . . . . . O1 O 0.55478(17) 0.59936(11) 0.42223(13) 0.0296(3) Uani 1 1 d . . . . . O2 O 0.86426(18) 0.61237(11) 0.67968(14) 0.0320(3) Uani 1 1 d . . . . . N2 N 0.7914(2) 0.47342(13) 0.51201(16) 0.0286(4) Uani 1 1 d . . . . . C8 C 0.5781(3) 0.63786(16) 0.80009(17) 0.0289(4) Uani 1 1 d . . . . . H8 H 0.673444 0.674417 0.806379 0.035 Uiso 1 1 calc R U . . . C10 C 0.6247(3) 0.54860(19) 0.8603(2) 0.0363(5) Uani 1 1 d . . . . . C15 C 0.5761(5) 0.4668(2) 0.8105(3) 0.0557(8) Uani 1 1 d . . . . . H15 H 0.508476 0.464362 0.738082 0.067 Uiso 1 1 calc R U . . . C14 C 0.6294(7) 0.3872(3) 0.8700(4) 0.0849(14) Uani 1 1 d . . . . . H14 H 0.599558 0.331737 0.835486 0.102 Uiso 1 1 calc R U . . . C13 C 0.7243(6) 0.3904(4) 0.9774(5) 0.0926(18) Uani 1 1 d . . . . . H13 H 0.758251 0.336988 1.016002 0.111 Uiso 1 1 calc R U . . . C12 C 0.7708(5) 0.4714(4) 1.0298(4) 0.0811(14) Uani 1 1 d . . . . . H12 H 0.835326 0.472979 1.103660 0.097 Uiso 1 1 calc R U . . . C11 C 0.7206(3) 0.5511(3) 0.9713(3) 0.0551(8) Uani 1 1 d . . . . . H11 H 0.751123 0.606219 1.006527 0.066 Uiso 1 1 calc R U . . . C1 C 0.3807(3) 0.63179(16) 0.62679(19) 0.0294(4) Uani 1 1 d . . . . . H1 H 0.312141 0.642386 0.682689 0.035 Uiso 1 1 calc R U . . . C2 C 0.3133(2) 0.62571(16) 0.50059(18) 0.0272(4) Uani 1 1 d . . . . . C4 C 0.0800(2) 0.64123(17) 0.3563(2) 0.0327(4) Uani 1 1 d . . . . . C5 C 0.1681(3) 0.63614(19) 0.2609(2) 0.0348(5) Uani 1 1 d . . . . . H5 H 0.120240 0.640722 0.181183 0.042 Uiso 1 1 calc R U . . . C6 C 0.3272(3) 0.62420(18) 0.28681(18) 0.0306(4) Uani 1 1 d . . . . . C7 C 0.4068(2) 0.61493(15) 0.40612(18) 0.0261(4) Uani 1 1 d . . . . . C17 C 0.9801(3) 0.46560(16) 0.6953(2) 0.0332(5) Uani 1 1 d . . . . . C16 C 0.9033(3) 0.43385(17) 0.5798(2) 0.0352(5) Uani 1 1 d . . . . . H16 H 0.938292 0.379494 0.551925 0.042 Uiso 1 1 calc R U . . . C23 C 0.7219(3) 0.43143(16) 0.3965(2) 0.0310(4) Uani 1 1 d . . . . . H23 H 0.701409 0.480240 0.337357 0.037 Uiso 1 1 calc R U . . . C25 C 0.5641(3) 0.39061(16) 0.4121(2) 0.0338(5) Uani 1 1 d . . . . . C26 C 0.4454(3) 0.3912(2) 0.3148(3) 0.0451(6) Uani 1 1 d . . . . . H26 H 0.462399 0.417439 0.242040 0.054 Uiso 1 1 calc R U . . . C27 C 0.3008(3) 0.3526(2) 0.3255(3) 0.0568(8) Uani 1 1 d . . . . . H27 H 0.222209 0.352571 0.259535 0.068 Uiso 1 1 calc R U . . . C28 C 0.2733(4) 0.3142(2) 0.4338(4) 0.0569(8) Uani 1 1 d . . . . . H28 H 0.176238 0.289300 0.441285 0.068 Uiso 1 1 calc R U . . . C29 C 0.3913(4) 0.3132(2) 0.5300(3) 0.0528(7) Uani 1 1 d . . . . . H29 H 0.374170 0.287276 0.602857 0.063 Uiso 1 1 calc R U . . . C30 C 0.5358(3) 0.35078(18) 0.5189(2) 0.0409(5) Uani 1 1 d . . . . . H30 H 0.614885 0.349143 0.584481 0.049 Uiso 1 1 calc R U . . . C24 C 0.8274(3) 0.3639(2) 0.3439(2) 0.0421(6) Uani 1 1 d . . . . . H24A H 0.773872 0.339972 0.269636 0.063 Uiso 1 1 calc R U . . . H24B H 0.921564 0.393463 0.328476 0.063 Uiso 1 1 calc R U . . . H24C H 0.853164 0.315697 0.400538 0.063 Uiso 1 1 calc R U . . . C18 C 1.0767(3) 0.40393(19) 0.7660(2) 0.0429(6) Uani 1 1 d . . . . . H18 H 1.089232 0.345879 0.737492 0.051 Uiso 1 1 calc R U . . . C19 C 1.1525(3) 0.4293(2) 0.8771(3) 0.0451(6) Uani 1 1 d . . . . . C20 C 1.1427(3) 0.5166(2) 0.9175(2) 0.0429(6) Uani 1 1 d . . . . . H20 H 1.198879 0.534340 0.990815 0.051 Uiso 1 1 calc R U . . . C21 C 1.0492(2) 0.5771(2) 0.84837(19) 0.0342(4) Uani 1 1 d . . . . . C9 C 0.4635(3) 0.68915(19) 0.8673(2) 0.0391(5) Uani 1 1 d . . . . . H9A H 0.506356 0.694911 0.951019 0.059 Uiso 1 1 calc R U . . . H9B H 0.445584 0.747955 0.832362 0.059 Uiso 1 1 calc R U . . . H9C H 0.366341 0.656860 0.860919 0.059 Uiso 1 1 calc R U . . . C3 C 0.1500(2) 0.63698(17) 0.4738(2) 0.0308(4) Uani 1 1 d . . . . . H3 H 0.089516 0.641546 0.536447 0.037 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 Cu1 0.02221(11) 0.03107(12) 0.02409(11) -0.00165(11) -0.00130(7) 0.00260(10) Cl1 0.0386(3) 0.0838(5) 0.0234(2) 0.0015(3) 0.0064(2) 0.0031(3) Cl2 0.0216(2) 0.0564(4) 0.0539(3) 0.0051(3) -0.0028(2) 0.0015(2) N1 0.0284(8) 0.0294(9) 0.0198(7) 0.0021(6) 0.0012(6) 0.0008(7) C22 0.0231(9) 0.0340(11) 0.0282(9) -0.0009(8) 0.0003(7) -0.0022(8) Cl3 0.0499(4) 0.0474(4) 0.0522(4) -0.0167(3) -0.0106(3) -0.0044(3) Cl4 0.0825(7) 0.0740(6) 0.0690(5) 0.0234(5) -0.0282(5) 0.0216(5) O1 0.0228(6) 0.0418(10) 0.0237(6) 0.0004(6) 0.0017(5) 0.0052(6) O2 0.0278(7) 0.0307(7) 0.0346(7) -0.0033(6) -0.0064(6) 0.0011(6) N2 0.0265(8) 0.0307(9) 0.0278(8) -0.0027(7) 0.0010(7) 0.0006(7) C8 0.0308(10) 0.0358(12) 0.0195(8) 0.0023(8) 0.0014(7) -0.0012(8) C10 0.0355(11) 0.0442(12) 0.0302(11) 0.0109(9) 0.0085(9) 0.0060(10) C15 0.080(2) 0.0424(16) 0.0464(15) 0.0113(12) 0.0130(15) 0.0090(15) C14 0.125(4) 0.0446(19) 0.092(3) 0.026(2) 0.040(3) 0.019(2) C13 0.102(3) 0.086(3) 0.097(3) 0.064(3) 0.039(3) 0.051(3) C12 0.068(2) 0.108(4) 0.066(2) 0.054(2) 0.0050(19) 0.020(2) C11 0.0457(15) 0.076(2) 0.0420(14) 0.0240(14) -0.0012(11) 0.0008(14) C1 0.0270(9) 0.0368(12) 0.0247(9) 0.0021(8) 0.0043(7) 0.0002(8) C2 0.0239(9) 0.0330(11) 0.0244(8) 0.0014(8) 0.0022(7) 0.0002(8) C4 0.0208(9) 0.0381(12) 0.0376(11) 0.0029(9) -0.0020(8) -0.0001(8) C5 0.0284(10) 0.0460(13) 0.0280(10) 0.0021(9) -0.0033(8) -0.0002(9) C6 0.0275(9) 0.0410(12) 0.0230(8) 0.0009(8) 0.0026(7) 0.0002(9) C7 0.0240(9) 0.0285(9) 0.0252(9) 0.0008(7) 0.0016(7) 0.0006(8) C17 0.0290(10) 0.0350(12) 0.0335(11) 0.0006(9) -0.0035(8) 0.0051(9) C16 0.0344(12) 0.0317(11) 0.0373(12) -0.0054(9) -0.0030(9) 0.0064(9) C23 0.0316(10) 0.0322(11) 0.0280(10) -0.0044(8) -0.0001(8) -0.0006(8) C25 0.0323(11) 0.0288(11) 0.0392(11) -0.0075(9) 0.0007(9) 0.0000(9) C26 0.0386(13) 0.0473(15) 0.0459(14) -0.0068(11) -0.0068(11) -0.0005(11) C27 0.0341(14) 0.0575(18) 0.074(2) -0.0133(16) -0.0100(14) -0.0027(13) C28 0.0373(14) 0.0440(16) 0.090(2) -0.0118(16) 0.0100(15) -0.0064(12) C29 0.0513(17) 0.0426(15) 0.0674(19) -0.0025(14) 0.0186(15) -0.0109(13) C30 0.0412(14) 0.0370(13) 0.0442(13) -0.0018(11) 0.0051(11) -0.0044(10) C24 0.0394(13) 0.0475(15) 0.0396(12) -0.0124(11) 0.0058(10) 0.0013(11) C18 0.0406(13) 0.0381(13) 0.0461(14) 0.0024(11) -0.0077(11) 0.0098(11) C19 0.0395(14) 0.0490(15) 0.0431(13) 0.0124(12) -0.0072(11) 0.0064(11) C20 0.0350(12) 0.0578(17) 0.0320(11) 0.0027(11) -0.0091(9) -0.0030(11) C21 0.0283(9) 0.0413(11) 0.0308(9) -0.0021(11) -0.0038(7) -0.0036(11) C9 0.0453(14) 0.0450(14) 0.0268(11) -0.0042(10) 0.0043(9) 0.0057(11) C3 0.0222(9) 0.0385(12) 0.0317(10) 0.0008(9) 0.0043(8) -0.0012(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 O1 Cu1 O2 150.92(7) . . ? O1 Cu1 N1 93.65(7) . . ? O2 Cu1 N1 97.28(7) . . ? O1 Cu1 N2 94.55(7) . . ? O2 Cu1 N2 91.95(7) . . ? N1 Cu1 N2 144.70(8) . . ? C1 N1 C8 119.39(18) . . ? C1 N1 Cu1 123.13(14) . . ? C8 N1 Cu1 117.19(13) . . ? O2 C22 C17 124.3(2) . . ? O2 C22 C21 120.2(2) . . ? C17 C22 C21 115.5(2) . . ? C7 O1 Cu1 127.87(13) . . ? C22 O2 Cu1 124.03(14) . . ? C16 N2 C23 120.1(2) . . ? C16 N2 Cu1 121.30(16) . . ? C23 N2 Cu1 117.92(14) . . ? N1 C8 C10 109.97(19) . . ? N1 C8 C9 115.27(19) . . ? C10 C8 C9 111.66(18) . . ? N1 C8 H8 106.5 . . ? C10 C8 H8 106.5 . . ? C9 C8 H8 106.5 . . ? C15 C10 C11 119.6(3) . . ? C15 C10 C8 123.0(2) . . ? C11 C10 C8 117.4(3) . . ? C10 C15 C14 119.3(4) . . ? C10 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C13 C14 C15 120.6(4) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C12 C11 119.4(4) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C12 C11 C10 120.2(4) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? N1 C1 C2 126.03(19) . . ? N1 C1 H1 117.0 . . ? C2 C1 H1 117.0 . . ? C3 C2 C7 120.61(18) . . ? C3 C2 C1 117.04(18) . . ? C7 C2 C1 122.22(18) . . ? C3 C4 C5 121.0(2) . . ? C3 C4 Cl2 120.26(17) . . ? C5 C4 Cl2 118.72(17) . . ? C6 C5 C4 118.7(2) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 123.44(19) . . ? C5 C6 Cl1 119.63(16) . . ? C7 C6 Cl1 116.92(16) . . ? O1 C7 C6 119.51(18) . . ? O1 C7 C2 124.80(18) . . ? C6 C7 C2 115.68(18) . . ? C18 C17 C22 121.1(2) . . ? C18 C17 C16 116.9(2) . . ? C22 C17 C16 122.0(2) . . ? N2 C16 C17 126.3(2) . . ? N2 C16 H16 116.8 . . ? C17 C16 H16 116.8 . . ? N2 C23 C25 109.31(18) . . ? N2 C23 C24 114.78(19) . . ? C25 C23 C24 111.9(2) . . ? N2 C23 H23 106.8 . . ? C25 C23 H23 106.8 . . ? C24 C23 H23 106.8 . . ? C30 C25 C26 118.6(3) . . ? C30 C25 C23 122.4(2) . . ? C26 C25 C23 119.0(2) . . ? C25 C26 C27 120.3(3) . . ? C25 C26 H26 119.8 . . ? C27 C26 H26 119.8 . . ? C28 C27 C26 120.4(3) . . ? C28 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? C29 C28 C27 119.2(3) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? C28 C29 C30 120.4(3) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C25 C30 C29 121.1(3) . . ? C25 C30 H30 119.5 . . ? C29 C30 H30 119.5 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C19 C18 C17 120.1(3) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.7(2) . . ? C18 C19 Cl4 120.0(2) . . ? C20 C19 Cl4 119.3(2) . . ? C21 C20 C19 119.3(2) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C22 123.1(3) . . ? C20 C21 Cl3 119.60(18) . . ? C22 C21 Cl3 117.2(2) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? 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 Cu1 O1 1.8785(14) . ? Cu1 O2 1.8924(15) . ? Cu1 N1 1.9807(17) . ? Cu1 N2 1.9970(19) . ? Cl1 C6 1.733(2) . ? Cl2 C4 1.742(2) . ? N1 C1 1.285(3) . ? N1 C8 1.490(2) . ? C22 O2 1.295(3) . ? C22 C17 1.412(3) . ? C22 C21 1.420(3) . ? Cl3 C21 1.739(3) . ? Cl4 C19 1.737(3) . ? O1 C7 1.286(2) . ? N2 C16 1.285(3) . ? N2 C23 1.482(3) . ? C8 C10 1.515(3) . ? C8 C9 1.525(3) . ? C8 H8 0.9800 . ? C10 C15 1.377(5) . ? C10 C11 1.392(4) . ? C15 C14 1.402(5) . ? C15 H15 0.9300 . ? C14 C13 1.357(7) . ? C14 H14 0.9300 . ? C13 C12 1.373(8) . ? C13 H13 0.9300 . ? C12 C11 1.391(5) . ? C12 H12 0.9300 . ? C11 H11 0.9300 . ? C1 C2 1.451(3) . ? C1 H1 0.9300 . ? C2 C3 1.410(3) . ? C2 C7 1.422(3) . ? C4 C3 1.368(3) . ? C4 C5 1.392(3) . ? C5 C6 1.376(3) . ? C5 H5 0.9300 . ? C6 C7 1.419(3) . ? C17 C18 1.406(3) . ? C17 C16 1.444(3) . ? C16 H16 0.9300 . ? C23 C25 1.522(3) . ? C23 C24 1.525(3) . ? C23 H23 0.9800 . ? C25 C30 1.382(4) . ? C25 C26 1.387(4) . ? C26 C27 1.394(4) . ? C26 H26 0.9300 . ? C27 C28 1.385(5) . ? C27 H27 0.9300 . ? C28 C29 1.375(5) . ? C28 H28 0.9300 . ? C29 C30 1.387(4) . ? C29 H29 0.9300 . ? C30 H30 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C18 C19 1.373(4) . ? C18 H18 0.9300 . ? C19 C20 1.378(4) . ? C20 C21 1.372(4) . ? C20 H20 0.9300 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C3 H3 0.9300 . ? 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 O2 Cu1 O1 C7 -124.33(19) . . . . ? N1 Cu1 O1 C7 -12.26(19) . . . . ? N2 Cu1 O1 C7 133.36(18) . . . . ? C17 C22 O2 Cu1 25.3(3) . . . . ? C21 C22 O2 Cu1 -155.24(16) . . . . ? O1 Cu1 O2 C22 -137.22(17) . . . . ? N1 Cu1 O2 C22 111.59(17) . . . . ? N2 Cu1 O2 C22 -34.25(18) . . . . ? C1 N1 C8 C10 108.5(2) . . . . ? Cu1 N1 C8 C10 -65.5(2) . . . . ? C1 N1 C8 C9 -18.8(3) . . . . ? Cu1 N1 C8 C9 167.23(17) . . . . ? N1 C8 C10 C15 -20.1(3) . . . . ? C9 C8 C10 C15 109.1(3) . . . . ? N1 C8 C10 C11 160.1(2) . . . . ? C9 C8 C10 C11 -70.6(3) . . . . ? C11 C10 C15 C14 -2.7(5) . . . . ? C8 C10 C15 C14 177.6(3) . . . . ? C10 C15 C14 C13 2.0(6) . . . . ? C15 C14 C13 C12 -0.4(7) . . . . ? C14 C13 C12 C11 -0.4(7) . . . . ? C13 C12 C11 C10 -0.4(6) . . . . ? C15 C10 C11 C12 2.0(4) . . . . ? C8 C10 C11 C12 -178.3(3) . . . . ? C8 N1 C1 C2 176.0(2) . . . . ? Cu1 N1 C1 C2 -10.3(3) . . . . ? N1 C1 C2 C3 -179.6(2) . . . . ? N1 C1 C2 C7 -3.7(4) . . . . ? C3 C4 C5 C6 1.8(4) . . . . ? Cl2 C4 C5 C6 -178.2(2) . . . . ? C4 C5 C6 C7 1.3(4) . . . . ? C4 C5 C6 Cl1 179.9(2) . . . . ? Cu1 O1 C7 C6 -178.43(17) . . . . ? Cu1 O1 C7 C2 2.8(3) . . . . ? C5 C6 C7 O1 176.4(2) . . . . ? Cl1 C6 C7 O1 -2.1(3) . . . . ? C5 C6 C7 C2 -4.7(4) . . . . ? Cl1 C6 C7 C2 176.69(18) . . . . ? C3 C2 C7 O1 -176.0(2) . . . . ? C1 C2 C7 O1 8.3(4) . . . . ? C3 C2 C7 C6 5.3(3) . . . . ? C1 C2 C7 C6 -170.5(2) . . . . ? O2 C22 C17 C18 -175.8(2) . . . . ? C21 C22 C17 C18 4.7(3) . . . . ? O2 C22 C17 C16 3.3(4) . . . . ? C21 C22 C17 C16 -176.1(2) . . . . ? C23 N2 C16 C17 -178.7(2) . . . . ? Cu1 N2 C16 C17 -8.1(4) . . . . ? C18 C17 C16 N2 167.3(3) . . . . ? C22 C17 C16 N2 -11.9(4) . . . . ? C16 N2 C23 C25 104.0(3) . . . . ? Cu1 N2 C23 C25 -67.0(2) . . . . ? C16 N2 C23 C24 -22.7(3) . . . . ? Cu1 N2 C23 C24 166.39(17) . . . . ? N2 C23 C25 C30 -35.6(3) . . . . ? C24 C23 C25 C30 92.7(3) . . . . ? N2 C23 C25 C26 146.1(2) . . . . ? C24 C23 C25 C26 -85.6(3) . . . . ? C30 C25 C26 C27 0.3(4) . . . . ? C23 C25 C26 C27 178.6(3) . . . . ? C25 C26 C27 C28 0.8(5) . . . . ? C26 C27 C28 C29 -1.1(5) . . . . ? C27 C28 C29 C30 0.4(5) . . . . ? C26 C25 C30 C29 -1.0(4) . . . . ? C23 C25 C30 C29 -179.3(3) . . . . ? C28 C29 C30 C25 0.6(5) . . . . ? C22 C17 C18 C19 -0.4(4) . . . . ? C16 C17 C18 C19 -179.6(3) . . . . ? C17 C18 C19 C20 -3.9(5) . . . . ? C17 C18 C19 Cl4 175.2(2) . . . . ? C18 C19 C20 C21 3.5(4) . . . . ? Cl4 C19 C20 C21 -175.6(2) . . . . ? C19 C20 C21 C22 1.2(4) . . . . ? C19 C20 C21 Cl3 178.5(2) . . . . ? O2 C22 C21 C20 175.3(2) . . . . ? C17 C22 C21 C20 -5.2(3) . . . . ? O2 C22 C21 Cl3 -2.0(3) . . . . ? C17 C22 C21 Cl3 177.47(17) . . . . ? C5 C4 C3 C2 -1.1(4) . . . . ? Cl2 C4 C3 C2 178.89(19) . . . . ? C7 C2 C3 C4 -2.6(4) . . . . ? C1 C2 C3 C4 173.4(2) . . . . ?