#------------------------------------------------------------------------------ #$Date: 2022-02-09 11:11:06 +0200 (Wed, 09 Feb 2022) $ #$Revision: 272869 $ #$URL: file:///home/coder/svn-repositories/cod/cif/8/10/45/8104549.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_8104549 loop_ _publ_author_name 'Wei, Baiying' 'Cao, Chenzhong' _publ_section_title ; Crystal structure of [6,6′-((1E,1′E)-(propane-1,3- diylbis(azaneylylidene))bis(methaneylylidene)) bis(3-chlorophenol)-\k 4 N,N′,O,O′] copper(II), C17H14Cl2CuN2O2 ; _journal_issue 6 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 1143 _journal_page_last 1144 _journal_paper_doi 10.1515/ncrs-2021-0249 _journal_volume 236 _journal_year 2021 _chemical_formula_moiety 'C17 H14 Cl2 Cu N2 O2' _chemical_formula_sum 'C17 H14 Cl2 Cu N2 O2' _chemical_formula_weight 412.74 _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 geom _cell_angle_alpha 90 _cell_angle_beta 94.159(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 22.743(4) _cell_length_b 8.0434(15) _cell_length_c 8.9388(17) _cell_measurement_reflns_used 979 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 19.87 _cell_measurement_theta_min 2.69 _cell_volume 1630.9(5) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_unetI/netI 0.0263 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 4151 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.003 _diffrn_reflns_theta_max 25.003 _diffrn_reflns_theta_min 2.687 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.679 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6456 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0508 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.8661. The \l/2 correction factor is Not present. ; _exptl_crystal_colour Black _exptl_crystal_density_diffrn 1.681 _exptl_crystal_description Block _exptl_crystal_F_000 836 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.497 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 123 _refine_ls_number_reflns 1449 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.090 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0376 _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^)+(0.0457P)^2^+1.0253P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0932 _refine_ls_wR_factor_ref 0.0997 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1154 _reflns_number_total 1449 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file suppl_j_ncrs-2021-0249_suppl.cif _cod_data_source_block z20200320a_0m _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. Automatic conversion script Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas ; _cod_original_cell_volume 1630.8(5) _cod_database_code 8104549 _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 0.799 _shelx_estimated_absorpt_t_min 0.709 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Restrained distances C9-C8 1.55 with sigma of 0.02 N1-C8 = N1_$1-C10 1.46 with sigma of 0.01 3. Rigid bond restraints C7, C6 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002 4. Others Fixed Sof: C8(0.5) H8A(0.5) H8B(0.5) C9(0.5) H9A(0.5) H9B(0.5) C10(0.5) H10A(0.5) H10B(0.5) 5.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B) 5.b Aromatic/amide H refined with riding coordinates: C2(H2), C4(H4), C5(H5), C7(H7) ; _shelx_res_file ; TITL z20200320a_0m_a.res in C2/c z20200320a_0m.res created by SHELXL-2018/3 at 22:02:15 on 09-Apr-2021 REM Old TITL Z20200320A_0m in C2/c REM SHELXT solution in C2/c: R1 0.182, Rweak 0.013, Alpha 0.052 REM 0.608 for 123 systematic absences, Orientation as input REM Formula found by SHELXT: C18 N2 O2 Cl2 Cu CELL 0.71073 22.7425 8.0434 8.9388 90 94.159 90 ZERR 4 0.0044 0.0015 0.0017 0 0.003 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H Cl Cu N O UNIT 68 56 8 4 8 8 EQIV $1 1-X,+Y,1.5-Z DFIX 1.55 C9 C8 DFIX 1.46 0.01 N1 C8 N1_$1 C10 DELU 0.002 0.002 C7 C6 L.S. 4 0 0 PLAN 5 SIZE 0.22 0.18 0.14 TEMP 23 BIND C10 N1_$1 HTAB BOND $H list 4 fmap 2 53 acta OMIT -3 50.02 OMIT 2 2 0 REM REM REM WGHT 0.045700 1.025300 FVAR 0.26878 CU1 4 0.500000 0.464948 0.750000 10.50000 0.07442 0.03629 = 0.07404 0.00000 0.00775 0.00000 CL1 3 0.287406 -0.061580 0.444592 11.00000 0.07479 0.13560 = 0.09229 -0.03115 -0.01154 -0.01905 O1 6 0.443277 0.294208 0.709312 11.00000 0.07117 0.04717 = 0.06695 0.00793 -0.01534 0.00014 N1 5 0.456439 0.624548 0.619066 11.00000 0.09936 0.04072 = 0.08766 0.00984 0.03045 0.01684 C1 1 0.400534 0.288174 0.603415 11.00000 0.05549 0.06398 = 0.05471 -0.00118 0.00441 0.01746 C2 1 0.367139 0.141394 0.584769 11.00000 0.05633 0.07358 = 0.05799 -0.00489 -0.00143 0.00624 AFIX 43 H2 2 0.373861 0.053845 0.651793 11.00000 -1.20000 AFIX 0 C3 1 0.324765 0.126650 0.468438 11.00000 0.05285 0.10876 = 0.05882 -0.01284 -0.00010 0.00642 C4 1 0.311395 0.253210 0.369561 11.00000 0.07597 0.13270 = 0.06742 -0.00117 -0.01069 0.02404 AFIX 43 H4 2 0.283212 0.239169 0.289861 11.00000 -1.20000 AFIX 0 C5 1 0.340513 0.400679 0.390953 11.00000 0.09158 0.11577 = 0.06248 0.02461 0.00733 0.04457 AFIX 43 H5 2 0.330381 0.488990 0.327046 11.00000 -1.20000 AFIX 0 C6 1 0.385716 0.424218 0.507224 11.00000 0.06988 0.07678 = 0.05475 0.01084 0.01049 0.03113 C7 1 0.412335 0.582854 0.526951 11.00000 0.09724 0.06659 = 0.06952 0.01985 0.02524 0.03607 AFIX 43 H7 2 0.396109 0.667446 0.466207 11.00000 -1.20000 AFIX 0 PART -1 C8 1 0.462993 0.808448 0.617982 10.50000 0.16611 0.03206 = 0.17776 -0.00476 0.01266 0.00643 AFIX 23 H8A 2 0.427850 0.859470 0.652911 10.50000 -1.20000 H8B 2 0.467233 0.846092 0.516234 10.50000 -1.20000 AFIX 0 C9 1 0.516572 0.862216 0.718217 10.50000 0.12448 0.02677 = 0.15649 0.00324 0.06192 -0.01189 AFIX 23 H9A 2 0.551721 0.827456 0.671390 10.50000 -1.20000 H9B 2 0.517028 0.982707 0.722659 10.50000 -1.20000 AFIX 0 C10 1 0.520027 0.797887 0.872456 10.50000 0.14252 0.04133 = 0.13362 -0.03642 0.07478 -0.03044 AFIX 23 H10A 2 0.481044 0.799724 0.909843 10.50000 -1.20000 H10B 2 0.545369 0.869600 0.936092 10.50000 -1.20000 AFIX 0 HKLF 4 REM z20200320a_0m_a.res in C2/c REM wR2 = 0.0997, GooF = S = 1.083, Restrained GooF = 1.090 for all data REM R1 = 0.0376 for 1154 Fo > 4sig(Fo) and 0.0493 for all 1449 data REM 123 parameters refined using 4 restraints END WGHT 0.0457 1.0265 REM Instructions for potential hydrogen bonds EQIV $2 x, -y+1, z-1/2 HTAB C7 O1_$2 REM Highest difference peak 0.497, deepest hole -0.358, 1-sigma level 0.049 Q1 1 0.2848 0.0415 0.3943 11.00000 0.05 0.50 Q2 1 0.2807 -0.0977 0.4450 11.00000 0.05 0.26 Q3 1 0.4595 0.5279 0.7312 11.00000 0.05 0.22 Q4 1 0.4195 0.2974 0.6667 11.00000 0.05 0.19 Q5 1 0.3473 0.5489 0.3471 11.00000 0.05 0.17 ; _shelx_res_checksum 56850 _shelx_hkl_file ; -4 0 0 443.26 6.60 -4 0 0 445.06 6.10 -6 0 0 729.93 9.70 -6 0 0 695.83 10.40 -8 0 0 3.50 0.80 -8 0 0 2.80 0.60 -10 0 0 775.92 11.40 -10 0 0 778.22 12.70 -12 0 0 7.10 1.30 -12 0 0 7.10 1.10 -14 0 0 195.68 5.00 -14 0 0 195.68 6.00 14 0 0 186.18 5.00 -16 0 0 20.00 2.10 -16 0 0 20.70 2.60 16 0 0 16.40 2.00 -18 0 0 191.18 5.60 18 0 0 196.88 5.80 -18 0 0 200.98 6.90 20 0 0 44.60 3.50 -20 0 0 35.70 3.80 -20 0 0 38.70 3.30 -22 0 0 19.50 3.00 -24 0 0 21.90 3.40 -26 0 0 3.60 1.80 -28 0 0 7.50 2.50 -1 -1 0 1635.64 19.30 -1 -1 0 1636.04 20.50 -1 1 0 1694.83 19.50 -3 -1 0 1904.31 22.30 -3 -1 0 1879.61 22.60 -3 1 0 1842.62 22.50 -5 -1 0 353.96 6.00 -5 -1 0 357.16 5.80 -5 1 0 358.16 6.10 -7 -1 0 1087.49 15.00 -7 -1 0 1116.69 15.00 -7 1 0 1098.19 13.40 -7 1 0 1080.29 15.40 -9 -1 0 1.00 0.50 -9 -1 0 0.90 0.60 -9 1 0 1.30 0.60 -9 1 0 2.20 0.50 -11 -1 0 577.64 10.40 -11 -1 0 572.64 9.90 -11 1 0 570.84 10.70 -11 1 0 576.04 8.60 -13 -1 0 126.09 4.10 -13 -1 0 121.29 4.40 13 -1 0 120.19 3.40 13 1 0 120.19 4.10 -13 1 0 122.69 3.30 -13 1 0 115.49 4.50 -15 -1 0 8.20 1.50 15 -1 0 6.60 1.20 -15 -1 0 2.90 1.00 -15 1 0 4.00 1.30 15 1 0 5.60 1.30 -15 1 0 7.20 1.10 -17 -1 0 143.09 5.00 17 -1 0 151.88 4.90 -17 -1 0 151.28 5.70 17 1 0 142.89 5.10 -17 1 0 147.29 4.60 -17 1 0 147.89 5.80 -19 -1 0 27.50 3.30 -19 -1 0 23.50 2.60 19 1 0 25.80 2.80 -19 1 0 34.70 3.90 -21 -1 0 90.39 4.40 -21 -1 0 95.89 5.10 -21 1 0 92.69 5.20 21 1 0 89.49 4.50 -23 -1 0 0.90 1.10 -23 -1 0 -0.90 1.00 23 1 0 -0.20 1.30 -23 1 0 1.90 1.60 -25 -1 0 32.20 4.20 -25 1 0 24.70 3.80 -27 -1 0 1.60 1.60 -27 1 0 4.40 2.00 0 -2 0 303.67 4.80 0 2 0 306.37 4.80 0 2 0 293.87 5.00 2 -2 0 24.00 0.90 -2 -2 0 24.60 1.20 -2 -2 0 25.00 1.20 -2 2 0 23.80 1.20 -2 2 0 25.00 0.90 2 2 0 25.10 1.30 -4 -2 0 521.95 8.30 -4 -2 0 520.45 7.90 -4 2 0 524.35 8.30 -6 -2 0 339.57 6.30 -6 -2 0 339.97 6.60 -6 2 0 343.37 6.60 -8 -2 0 769.82 12.00 -8 -2 0 765.82 12.20 -8 2 0 761.22 12.40 10 -2 0 552.14 7.30 -10 -2 0 518.65 9.80 -10 -2 0 545.55 9.90 10 2 0 553.64 10.10 -10 2 0 550.64 10.30 -10 2 0 553.64 7.30 12 -2 0 63.79 1.90 -12 -2 0 62.49 3.00 -12 -2 0 70.69 3.20 -12 2 0 67.29 1.90 12 2 0 66.39 3.20 -12 2 0 65.19 3.30 -14 -2 0 362.66 8.40 -14 -2 0 376.66 8.60 -14 2 0 368.66 9.00 14 2 0 381.36 8.70 -16 -2 0 -0.50 0.60 -16 -2 0 -0.20 0.60 16 2 0 -0.50 0.70 -16 2 0 -0.30 0.70 -18 -2 0 67.39 3.70 -18 -2 0 78.29 4.20 18 2 0 72.89 4.00 -18 2 0 64.39 5.00 -20 -2 0 7.50 1.80 -20 -2 0 7.90 2.00 -20 2 0 7.40 2.00 20 2 0 8.30 2.00 -22 -2 0 0.80 1.20 -22 -2 0 0.80 1.20 22 2 0 2.50 1.50 -22 2 0 1.90 1.50 -24 -2 0 25.80 3.40 -24 -2 0 29.90 3.90 -24 2 0 28.80 4.20 24 2 0 28.10 3.70 -26 -2 0 0.20 1.60 -26 2 0 3.20 1.80 -1 -3 0 227.98 4.70 1 -3 0 229.68 4.30 1 3 0 230.58 4.80 -1 3 0 227.88 4.40 -1 3 0 227.28 4.80 1 3 0 235.58 4.80 -3 -3 0 264.97 5.60 3 -3 0 275.87 4.40 -3 3 0 268.97 5.60 3 3 0 269.07 5.60 -3 3 0 272.17 4.40 -5 -3 0 366.96 7.30 -5 -3 0 375.26 6.90 -5 3 0 362.56 7.20 -5 3 0 371.46 5.00 5 3 0 374.16 7.40 -7 -3 0 1232.68 18.10 -7 -3 0 1234.18 17.40 -7 3 0 1229.08 18.00 7 3 0 1245.88 18.20 -9 -3 0 207.28 5.40 -9 -3 0 205.78 5.70 9 3 0 205.08 5.70 -9 3 0 202.88 5.60 -11 -3 0 258.47 6.80 -11 -3 0 249.48 6.50 11 3 0 257.17 6.90 -11 3 0 254.47 6.90 -13 -3 0 59.89 3.30 -13 -3 0 65.79 3.40 13 3 0 59.49 3.40 -13 3 0 63.59 3.40 -15 -3 0 69.29 3.70 -15 -3 0 68.39 3.70 -15 3 0 64.89 3.80 15 3 0 71.19 3.90 -17 -3 0 29.60 3.20 -17 -3 0 30.70 3.30 17 3 0 26.50 3.00 -17 3 0 28.00 3.30 -19 -3 0 1.80 1.20 -19 -3 0 0.80 1.10 -19 3 0 0.70 1.00 19 3 0 0.70 1.20 -21 -3 0 11.80 2.40 -21 -3 0 13.00 2.50 21 3 0 10.00 2.30 -21 3 0 14.90 3.00 -23 -3 0 2.60 1.50 -23 -3 0 0.80 1.20 23 3 0 1.10 1.50 -23 3 0 2.10 1.30 -25 -3 0 5.70 2.10 -25 -3 0 1.60 1.50 -25 3 0 6.50 2.50 25 3 0 1.90 2.00 -27 -3 0 -0.30 1.40 -27 -3 0 -0.10 1.30 -27 3 0 2.60 1.80 27 3 0 1.80 2.10 0 -4 0 1.40 0.60 0 4 0 1.20 0.50 0 4 0 1.30 0.60 2 -4 0 57.29 2.10 -2 -4 0 58.99 2.50 -2 4 0 54.39 2.50 2 4 0 56.49 2.50 -2 4 0 58.69 2.10 2 4 0 56.59 2.50 4 -4 0 257.07 4.50 -4 -4 0 255.67 6.10 4 4 0 256.27 6.10 -4 4 0 248.78 6.00 -4 4 0 253.27 4.50 -6 -4 0 11.10 1.60 -6 -4 0 12.00 1.50 -6 4 0 10.70 1.60 -6 4 0 14.00 0.90 6 4 0 11.90 1.60 -8 -4 0 70.09 3.10 -8 -4 0 71.29 3.40 -8 4 0 79.49 3.50 8 4 0 72.09 3.50 -10 -4 0 169.58 5.70 -10 -4 0 172.48 5.20 10 4 0 174.98 5.80 -10 4 0 174.68 5.60 -12 -4 0 54.79 4.30 -12 -4 0 45.40 3.50 12 4 0 45.00 3.70 -12 4 0 47.70 3.90 -14 -4 0 41.20 4.00 -14 -4 0 34.50 3.20 14 4 0 24.70 3.00 -14 4 0 34.20 3.60 -16 -4 0 13.40 2.20 -16 -4 0 11.90 2.20 -16 4 0 11.10 2.20 16 4 0 9.30 2.00 -18 -4 0 24.90 3.30 -18 -4 0 20.40 2.90 18 4 0 19.30 3.00 -18 4 0 22.00 3.30 -20 -4 0 19.30 2.80 -20 -4 0 20.60 3.10 -20 4 0 25.80 3.80 20 4 0 14.20 2.60 -22 -4 0 2.30 1.50 -22 -4 0 2.60 1.60 -22 4 0 3.80 1.80 22 4 0 3.00 1.90 -24 -4 0 1.80 1.60 -24 -4 0 0.10 1.50 -24 4 0 2.30 1.70 24 4 0 1.20 1.90 -26 -4 0 1.10 1.60 -26 -4 0 4.20 2.00 26 4 0 0.40 2.00 -26 4 0 0.40 1.60 -1 -5 0 37.40 2.80 1 -5 0 35.70 2.00 -1 5 0 33.80 2.80 -1 5 0 32.90 1.90 1 5 0 34.90 2.70 1 5 0 38.90 2.80 -3 -5 0 8.70 1.50 3 -5 0 10.90 1.30 3 5 0 12.60 1.80 -3 5 0 10.30 1.30 3 5 0 10.00 1.50 -3 5 0 9.30 1.50 -5 -5 0 52.29 2.90 5 5 0 55.59 3.00 -5 5 0 55.89 3.00 -7 -5 0 0.10 0.70 7 5 0 0.80 0.80 -7 5 0 0.70 0.80 -9 -5 0 24.60 2.50 -9 -5 0 26.10 2.90 -9 5 0 22.80 2.70 9 5 0 26.30 2.80 -11 -5 0 31.50 3.30 -11 -5 0 42.70 3.40 11 5 0 34.20 3.30 -11 5 0 37.30 3.50 -13 -5 0 9.60 2.00 -13 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3 -9 0.80 1.50 1 -3 -9 18.30 3.20 1 3 -9 19.50 3.40 -1 -3 -9 -1.40 1.10 -1 3 -9 1.00 1.40 -3 -3 -9 13.20 2.80 -3 3 -9 10.00 2.50 -5 -3 -9 6.10 2.20 -5 3 -9 8.50 2.40 -7 -3 -9 -0.70 1.30 -7 3 -9 0.20 1.40 -9 -3 -9 2.70 2.00 -9 3 -9 1.10 1.50 -11 -3 -9 -1.90 1.40 -11 3 -9 1.70 1.60 14 4 -9 -3.10 1.00 12 4 -9 1.80 2.10 10 4 -9 3.40 2.00 8 4 -9 7.00 2.50 8 4 -9 11.40 2.50 6 4 -9 0.60 1.50 6 4 -9 -0.90 1.40 4 -4 -9 3.20 1.70 4 4 -9 4.10 2.00 2 -4 -9 1.40 1.60 2 4 -9 0.60 1.40 0 -4 -9 6.90 2.30 0 4 -9 2.50 2.00 -2 -4 -9 12.20 2.80 -2 4 -9 10.10 2.60 -4 -4 -9 0.00 1.30 -4 4 -9 1.30 1.60 -6 -4 -9 17.70 3.30 -6 4 -9 17.00 3.10 -8 -4 -9 0.40 1.60 -8 4 -9 0.70 1.60 -10 -4 -9 1.50 1.70 -10 4 -9 0.60 1.60 9 5 -9 0.80 1.50 9 5 -9 0.30 1.60 7 5 -9 6.20 2.30 7 5 -9 6.50 2.30 5 5 -9 3.60 2.00 5 5 -9 -1.20 1.50 3 5 -9 0.80 1.60 3 5 -9 2.10 1.90 1 -5 -9 18.40 3.40 1 5 -9 18.50 3.50 1 5 -9 14.50 2.90 -1 -5 -9 3.40 2.00 -1 5 -9 1.80 1.60 -1 5 -9 1.10 1.40 -3 -5 -9 3.10 2.00 -3 5 -9 3.70 1.90 -5 -5 -9 0.20 1.60 -5 5 -9 1.60 1.70 -7 -5 -9 10.50 3.00 -7 5 -9 8.80 2.40 14 0 -10 7.90 2.70 12 0 -10 5.20 2.30 10 0 -10 8.30 2.60 8 0 -10 -0.30 1.70 6 0 -10 21.60 3.70 4 0 -10 48.10 5.00 2 0 -10 0.60 1.30 0 0 -10 -1.20 1.40 -2 0 -10 -1.50 1.20 -4 0 -10 2.70 1.80 -6 0 -10 4.60 2.00 -8 0 -10 3.00 1.80 -10 0 -10 1.40 1.40 13 -1 -10 2.60 2.20 13 1 -10 3.60 2.30 11 -1 -10 5.80 2.40 11 1 -10 6.00 2.40 9 -1 -10 1.10 1.90 9 1 -10 1.60 2.10 7 -1 -10 10.00 2.70 7 1 -10 5.50 2.40 5 -1 -10 2.20 1.90 5 1 -10 1.40 1.60 3 -1 -10 27.40 4.00 3 1 -10 26.40 3.80 1 -1 -10 3.10 1.80 1 1 -10 4.00 2.00 -1 -1 -10 0.80 1.40 -1 1 -10 0.90 1.30 -3 -1 -10 1.70 1.70 -3 1 -10 0.90 1.40 -5 -1 -10 -0.10 1.50 -5 1 -10 2.10 1.70 -7 -1 -10 7.00 2.30 -7 1 -10 5.70 2.10 -9 -1 -10 -0.90 1.20 -9 1 -10 0.20 1.50 12 2 -10 3.70 2.30 10 -2 -10 2.90 2.00 10 2 -10 2.80 2.20 8 -2 -10 0.90 1.70 8 2 -10 -0.10 1.70 6 -2 -10 2.00 1.80 6 2 -10 1.30 2.10 4 -2 -10 3.30 1.90 4 2 -10 0.30 1.40 2 -2 -10 5.30 2.10 2 2 -10 6.30 2.20 0 -2 -10 8.00 2.50 0 2 -10 6.80 2.30 -2 -2 -10 -1.00 1.40 -2 2 -10 1.80 1.50 -4 -2 -10 7.20 2.60 -4 2 -10 8.50 2.50 -6 -2 -10 1.20 1.40 -6 2 -10 1.00 1.70 -8 -2 -10 5.30 2.50 -8 2 -10 -0.70 1.50 11 3 -10 2.70 1.90 9 3 -10 0.60 2.00 7 -3 -10 2.50 2.00 7 3 -10 -0.60 1.50 5 -3 -10 2.50 1.70 5 3 -10 0.90 1.60 3 -3 -10 2.90 2.10 3 3 -10 3.30 2.20 1 -3 -10 0.50 1.80 1 3 -10 0.00 1.40 -1 -3 -10 4.60 2.20 -1 3 -10 7.60 2.40 -3 -3 -10 6.10 2.30 -3 3 -10 3.90 2.10 -5 -3 -10 2.70 1.80 -5 3 -10 2.90 2.00 -7 -3 -10 -0.60 1.50 -7 3 -10 2.30 1.90 6 4 -10 1.60 1.90 4 -4 -10 1.60 1.80 4 4 -10 1.50 1.90 2 -4 -10 6.00 2.30 2 4 -10 4.90 2.50 0 -4 -10 0.30 1.80 0 4 -10 0.90 2.00 -2 -4 -10 0.00 1.50 -2 4 -10 -0.30 1.60 6 0 -11 -1.20 1.40 4 0 -11 0.90 1.70 2 0 -11 -0.20 1.60 0 0 -11 0.80 1.60 -2 0 -11 0.00 1.30 5 -1 -11 2.00 2.00 5 1 -11 1.20 1.90 3 -1 -11 0.70 1.80 3 1 -11 0.10 1.80 1 -1 -11 0.90 1.80 1 1 -11 0.40 1.60 -1 -1 -11 0.10 1.40 -1 1 -11 0.50 1.80 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 87094 _olex2_submission_special_instructions 'No special instructions were received' 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 Cu1 Cu 0.500000 0.46495(6) 0.750000 0.0615(2) Uani 1 2 d S T P A . Cl1 Cl 0.28741(5) -0.06158(17) 0.44459(13) 0.1018(4) Uani 1 1 d . . . . . O1 O 0.44328(10) 0.2942(3) 0.7093(3) 0.0628(6) Uani 1 1 d . . . . . N1 N 0.45644(15) 0.6245(3) 0.6191(4) 0.0748(9) Uani 1 1 d D . . . . C1 C 0.40053(13) 0.2882(4) 0.6034(4) 0.0580(8) Uani 1 1 d . . . . . C2 C 0.36714(13) 0.1414(5) 0.5848(4) 0.0629(9) Uani 1 1 d . . . . . H2 H 0.373861 0.053845 0.651793 0.075 Uiso 1 1 calc R . . . . C3 C 0.32476(14) 0.1267(6) 0.4684(4) 0.0737(10) Uani 1 1 d . . . . . C4 C 0.31140(18) 0.2532(7) 0.3696(5) 0.0928(13) Uani 1 1 d . . . . . H4 H 0.283212 0.239169 0.289861 0.111 Uiso 1 1 calc R . . . . C5 C 0.34051(19) 0.4007(7) 0.3910(4) 0.0899(13) Uani 1 1 d . . . . . H5 H 0.330381 0.488990 0.327046 0.108 Uiso 1 1 calc R . . . . C6 C 0.38572(15) 0.4242(5) 0.5072(4) 0.0668(9) Uani 1 1 d . U . . . C7 C 0.41233(19) 0.5829(5) 0.5270(5) 0.0768(10) Uani 1 1 d . U . . . H7 H 0.396109 0.667446 0.466207 0.092 Uiso 1 1 calc R . . . . C8 C 0.4630(11) 0.8084(12) 0.618(3) 0.125(9) Uani 0.5 1 d D . . A -1 H8A H 0.427850 0.859470 0.652911 0.150 Uiso 0.5 1 calc R . . A -1 H8B H 0.467233 0.846092 0.516234 0.150 Uiso 0.5 1 calc R . . A -1 C9 C 0.5166(5) 0.8622(9) 0.7182(16) 0.100(4) Uani 0.5 1 d D . . A -1 H9A H 0.551721 0.827456 0.671390 0.120 Uiso 0.5 1 calc R . . A -1 H9B H 0.517028 0.982707 0.722659 0.120 Uiso 0.5 1 calc R . . A -1 C10 C 0.5200(10) 0.7979(13) 0.872(2) 0.103(9) Uani 0.5 1 d D . . A -1 H10A H 0.481044 0.799724 0.909843 0.123 Uiso 0.5 1 calc R . . A -1 H10B H 0.545369 0.869600 0.936092 0.123 Uiso 0.5 1 calc R . . A -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0744(4) 0.0363(3) 0.0740(4) 0.000 0.0078(3) 0.000 Cl1 0.0748(6) 0.1356(11) 0.0923(8) -0.0311(7) -0.0115(6) -0.0190(6) O1 0.0712(13) 0.0472(12) 0.0669(14) 0.0079(11) -0.0153(12) 0.0001(10) N1 0.099(2) 0.0407(16) 0.088(2) 0.0098(15) 0.0305(19) 0.0168(16) C1 0.0555(18) 0.064(2) 0.055(2) -0.0012(16) 0.0044(16) 0.0175(16) C2 0.0563(18) 0.074(2) 0.058(2) -0.0049(18) -0.0014(16) 0.0062(17) C3 0.0529(19) 0.109(3) 0.059(2) -0.013(2) -0.0001(17) 0.006(2) C4 0.076(3) 0.133(4) 0.067(3) -0.001(3) -0.011(2) 0.024(3) C5 0.092(3) 0.116(4) 0.062(3) 0.025(2) 0.007(2) 0.045(3) C6 0.070(2) 0.0768(19) 0.055(2) 0.0108(18) 0.0105(17) 0.0311(16) C7 0.097(3) 0.0666(19) 0.070(2) 0.0198(19) 0.025(2) 0.0361(18) C8 0.166(17) 0.032(7) 0.18(2) -0.005(9) 0.013(13) 0.006(8) C9 0.124(10) 0.027(4) 0.156(13) 0.003(6) 0.062(8) -0.012(5) C10 0.143(15) 0.041(8) 0.134(17) -0.036(10) 0.075(14) -0.030(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' 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' 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 O1 Cu1 O1 87.50(13) 2_656 . O1 Cu1 N1 93.00(12) . . O1 Cu1 N1 153.53(11) 2_656 . O1 Cu1 N1 93.00(12) 2_656 2_656 O1 Cu1 N1 153.53(11) . 2_656 N1 Cu1 N1 98.0(2) 2_656 . C1 O1 Cu1 128.6(2) . . C7 N1 Cu1 123.1(3) . . C7 N1 C8 109.1(9) . . C8 N1 Cu1 127.6(9) . . O1 C1 C2 118.9(3) . . O1 C1 C6 122.8(3) . . C2 C1 C6 118.3(3) . . C1 C2 H2 119.8 . . C3 C2 C1 120.4(4) . . C3 C2 H2 119.8 . . C2 C3 Cl1 118.6(3) . . C4 C3 Cl1 119.0(3) . . C4 C3 C2 122.5(4) . . C3 C4 H4 120.9 . . C5 C4 C3 118.2(4) . . C5 C4 H4 120.9 . . C4 C5 H5 118.8 . . C4 C5 C6 122.4(4) . . C6 C5 H5 118.8 . . C1 C6 C5 117.9(4) . . C1 C6 C7 122.6(3) . . C7 C6 C5 119.4(4) . . N1 C7 C6 128.0(3) . . N1 C7 H7 116.0 . . C6 C7 H7 116.0 . . N1 C8 H8A 109.5 . . N1 C8 H8B 109.5 . . N1 C8 C9 110.8(12) . . H8A C8 H8B 108.1 . . C9 C8 H8A 109.5 . . C9 C8 H8B 109.5 . . C8 C9 H9A 108.3 . . C8 C9 H9B 108.3 . . H9A C9 H9B 107.4 . . C10 C9 C8 116.0(14) . . C10 C9 H9A 108.3 . . C10 C9 H9B 108.3 . . N1 C10 H10A 109.3 2_656 . N1 C10 H10B 109.3 2_656 . C9 C10 N1 111.8(11) . 2_656 C9 C10 H10A 109.3 . . C9 C10 H10B 109.3 . . H10A C10 H10B 107.9 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cu1 O1 1.901(2) 2_656 Cu1 O1 1.901(2) . Cu1 N1 1.957(3) . Cu1 N1 1.957(3) 2_656 Cl1 C3 1.742(4) . O1 C1 1.308(4) . N1 C7 1.295(5) . N1 C8 1.487(9) . C1 C2 1.407(5) . C1 C6 1.417(5) . C2 H2 0.9300 . C2 C3 1.371(4) . C3 C4 1.368(6) . C4 H4 0.9300 . C4 C5 1.365(6) . C5 H5 0.9300 . C5 C6 1.421(6) . C6 C7 1.418(6) . C7 H7 0.9300 . C8 H8A 0.9700 . C8 H8B 0.9700 . C8 C9 1.522(18) . C9 H9A 0.9700 . C9 H9B 0.9700 . C9 C10 1.47(2) . C10 H10A 0.9700 . C10 H10B 0.9700 .