#------------------------------------------------------------------------------ #$Date: 2020-10-06 11:08:03 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257487 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/51/7235172.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_7235172 loop_ _publ_author_name 'Jiang, Chunli' 'Luo, Qianqian' 'Fu, Hanmei' 'Lin, Hechun' 'Luo, Chunhua' 'Wang, Jianlu' 'Meng, Xiangjian' 'Peng, Hui' 'Duan, Chun-Gang' 'Chu, Junhao' _publ_section_title ; Ferroelectricity and antiferromagnetism in organic--inorganic hybrid (1,4-bis(imidazol-1-ylmethyl)benzene)CuCl4·H2O ; _journal_issue 3 _journal_name_full CrystEngComm _journal_page_first 587 _journal_page_last 592 _journal_paper_doi 10.1039/C9CE01607D _journal_volume 22 _journal_year 2020 _chemical_formula_moiety 'C14 H16 N4, Cl4 Cu, H2 O' _chemical_formula_sum 'C14 H18 Cl4 Cu N4 O' _chemical_formula_weight 463.66 _space_group_crystal_system monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yc' _space_group_name_H-M_alt 'P 1 c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2017-05-12 _audit_creation_method ; Olex2 1.2-beta (compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227) ; _audit_update_record ; 2019-08-01 deposited with the CCDC. 2019-11-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.7160(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.1235(2) _cell_length_b 11.1935(4) _cell_length_c 11.6744(4) _cell_measurement_reflns_used 8350 _cell_measurement_temperature 173.15 _cell_measurement_theta_max 68.14 _cell_measurement_theta_min 3.82 _cell_volume 922.45(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 173.15 _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_unetI/netI 0.0451 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 8084 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.185 _diffrn_reflns_theta_min 3.949 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 7.089 _exptl_absorpt_correction_T_max 0.7530 _exptl_absorpt_correction_T_min 0.2746 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1449 before and 0.0673 after correction. The Ratio of minimum to maximum transmission is 0.3647. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.669 _exptl_crystal_description block _exptl_crystal_F_000 470 _refine_diff_density_max 0.386 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.120 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.049(18) _refine_ls_extinction_coef 0.0252(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 2993 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.121 _refine_ls_R_factor_all 0.0269 _refine_ls_R_factor_gt 0.0268 _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^)+(0.0409P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.0678 _reflns_Friedel_coverage 0.993 _reflns_Friedel_fraction_full 0.990 _reflns_Friedel_fraction_max 0.990 _reflns_number_gt 2979 _reflns_number_total 2993 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ce01607d2.cif _cod_data_source_block b _cod_depositor_comments ;Adding full bibliography for 7235172.cif. Adding full bibliography for 7235172.cif. ; _cod_database_code 7235172 _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. ; _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.951(18) 0.049(18) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All O(H,H) groups 3.a Riding coordinates: O1(H1A,H1B) 3.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C9(H9A,H9B) 3.c Aromatic/amide H refined with riding coordinates: N4(H4), N2(H2), C1(H1), C6(H6), C10(H10), C7(H7), C11(H11), C12(H12), C13(H13), C2(H2A), C14(H14), C3(H3) ; _shelx_res_file ; b.res created by SHELXL-2014/7 TITL b_a.res in Pc CELL 1.54178 7.1235 11.1935 11.6744 90 97.716 90 ZERR 2 0.0002 0.0004 0.0004 0 0.001 0 LATT -1 SYMM +X,-Y,0.5+Z SFAC C H Cl Cu N O UNIT 28 36 8 2 8 2 L.S. 5 PLAN -20 TEMP -100 BOND $H CONF MORE -1 fmap 2 acta TWIN -1 0 0 0 -1 0 0 0 -1 2 REM REM REM WGHT 0.040900 EXTI 0.025198 BASF 0.04888 FVAR 0.92853 N1 5 0.943274 0.283621 0.313049 11.00000 0.01276 0.01377 = 0.02342 -0.00275 0.00211 0.00196 N4 5 0.377517 0.854416 0.721298 11.00000 0.02110 0.01168 = 0.03030 -0.00420 0.00215 0.00204 AFIX 43 H4 2 0.372135 0.930963 0.737732 11.00000 -1.20000 AFIX 0 N3 5 0.360773 0.690158 0.625347 11.00000 0.01240 0.01162 = 0.01808 -0.00027 0.00197 0.00078 N2 5 0.862474 0.123704 0.216853 11.00000 0.02354 0.01700 = 0.03745 -0.00928 0.00452 -0.00016 AFIX 43 H2 2 0.838016 0.048188 0.199994 11.00000 -1.20000 AFIX 0 C1 1 0.922450 0.166170 0.322043 11.00000 0.01978 0.01508 = 0.03050 -0.00076 0.00152 0.00173 AFIX 43 H1 2 0.946098 0.120608 0.391130 11.00000 -1.20000 AFIX 0 C6 1 0.778051 0.544245 0.399723 11.00000 0.01901 0.01162 = 0.02259 -0.00043 0.00383 -0.00162 AFIX 43 H6 2 0.854614 0.583236 0.350489 11.00000 -1.20000 AFIX 0 C10 1 0.337690 0.807698 0.616531 11.00000 0.01907 0.01106 = 0.02493 0.00050 0.00321 0.00303 AFIX 43 H10 2 0.299326 0.850771 0.547220 11.00000 -1.20000 AFIX 0 C8 1 0.503115 0.544516 0.501418 11.00000 0.01608 0.01124 = 0.01910 -0.00503 0.00067 -0.00003 C4 1 1.000286 0.367426 0.409816 11.00000 0.01499 0.01717 = 0.02612 -0.00593 -0.00080 0.00134 AFIX 23 H4A 2 1.090456 0.426880 0.386074 11.00000 -1.20000 H4B 2 1.065124 0.322693 0.476890 11.00000 -1.20000 AFIX 0 C7 1 0.614847 0.599766 0.427213 11.00000 0.02175 0.00856 = 0.02661 -0.00027 0.00266 0.00179 AFIX 43 H7 2 0.579259 0.675799 0.395241 11.00000 -1.20000 AFIX 0 C11 1 0.428291 0.765681 0.800111 11.00000 0.02251 0.02513 = 0.01951 -0.00566 0.00118 0.00081 AFIX 43 H11 2 0.464146 0.775028 0.880969 11.00000 -1.20000 AFIX 0 C9 1 0.324200 0.603684 0.529616 11.00000 0.01657 0.01667 = 0.01920 -0.00376 -0.00022 -0.00038 AFIX 23 H9A 2 0.261780 0.645422 0.459965 11.00000 -1.20000 H9B 2 0.236146 0.541477 0.550668 11.00000 -1.20000 AFIX 0 C12 1 0.417235 0.661870 0.739856 11.00000 0.02093 0.01643 = 0.02009 0.00216 0.00124 0.00482 AFIX 43 H12 2 0.443441 0.584176 0.770665 11.00000 -1.20000 AFIX 0 C5 1 0.829413 0.431158 0.444495 11.00000 0.01430 0.00979 = 0.02384 -0.00551 -0.00102 -0.00013 C13 1 0.557480 0.432493 0.547824 11.00000 0.02351 0.01499 = 0.02305 0.00152 0.00705 -0.00236 AFIX 43 H13 2 0.483223 0.394187 0.598809 11.00000 -1.20000 AFIX 0 C2 1 0.844814 0.216092 0.138956 11.00000 0.02316 0.03069 = 0.02027 -0.00453 0.00389 0.00215 AFIX 43 H2A 2 0.805140 0.210446 0.058136 11.00000 -1.20000 AFIX 0 C14 1 0.719574 0.377193 0.519575 11.00000 0.02135 0.01183 = 0.02673 0.00122 0.00199 0.00349 AFIX 43 H14 2 0.755842 0.301461 0.552014 11.00000 -1.20000 AFIX 0 C3 1 0.894607 0.316338 0.199239 11.00000 0.02260 0.02096 = 0.02469 -0.00079 0.00585 0.00155 AFIX 43 H3 2 0.895917 0.395032 0.168881 11.00000 -1.20000 AFIX 0 CU1 4 0.215500 0.187414 0.752358 11.00000 0.01897 0.01214 = 0.02035 -0.00038 0.00437 0.00238 CL1 3 0.156363 0.382278 0.717489 11.00000 0.02390 0.01215 = 0.02446 0.00149 0.00560 0.00329 CL2 3 0.462278 0.091423 0.857414 11.00000 0.02121 0.01521 = 0.02475 -0.00353 -0.00139 0.00282 CL3 3 -0.002811 0.151331 0.868382 11.00000 0.02147 0.02539 = 0.02823 -0.00001 0.00823 -0.00359 CL4 3 0.273410 0.124179 0.577640 11.00000 0.03463 0.02408 = 0.02024 -0.00299 0.00381 0.01095 O1 6 0.730663 0.094871 0.634460 11.00000 0.03254 0.02998 = 0.05530 0.01608 0.00258 0.00453 AFIX 3 H1A 2 0.619283 0.115221 0.609090 11.00000 -1.50000 H1B 2 0.780363 0.139241 0.689520 11.00000 -1.50000 AFIX 0 HKLF 4 REM b_a.res in Pc REM R1 = 0.0268 for 2979 Fo > 4sig(Fo) and 0.0269 for all 2993 data REM 219 parameters refined using 2 restraints END WGHT 0.0409 0.0000 REM Highest difference peak 0.386, deepest hole -0.697, 1-sigma level 0.120 Q1 1 -0.0987 0.2744 0.7457 11.00000 0.05 0.39 Q2 1 0.3940 0.1175 0.7647 11.00000 0.05 0.37 Q3 1 0.2710 0.0394 0.8448 11.00000 0.05 0.36 Q4 1 0.4179 0.2498 0.7531 11.00000 0.05 0.36 Q5 1 -0.0459 0.3242 0.7249 11.00000 0.05 0.35 Q6 1 0.3831 0.3176 0.7217 11.00000 0.05 0.34 Q7 1 0.2986 0.1864 0.8254 11.00000 0.05 0.34 Q8 1 0.4752 0.1812 0.5752 11.00000 0.05 0.34 Q9 1 0.2769 0.1583 0.8329 11.00000 0.05 0.34 Q10 1 -0.0461 0.4327 0.7139 11.00000 0.05 0.32 Q11 1 -0.0654 0.1587 0.8109 11.00000 0.05 0.32 Q12 1 0.5222 0.1833 0.5225 11.00000 0.05 0.32 Q13 1 0.3134 0.6198 0.4984 11.00000 0.05 0.32 Q14 1 0.4273 0.4029 0.6581 11.00000 0.05 0.32 Q15 1 0.3719 0.4380 0.7204 11.00000 0.05 0.31 Q16 1 0.8754 0.6507 0.2988 11.00000 0.05 0.30 Q17 1 0.8773 0.5980 0.2829 11.00000 0.05 0.30 Q18 1 0.4204 1.0445 0.7963 11.00000 0.05 0.30 Q19 1 -0.2401 0.2265 0.9056 11.00000 0.05 0.29 Q20 1 0.1624 0.8252 0.7200 11.00000 0.05 0.28 ; _shelx_res_checksum 50920 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, 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 N1 N 0.9433(4) 0.2836(2) 0.3130(3) 0.0167(6) Uani 1 1 d . N4 N 0.3775(4) 0.8544(3) 0.7213(3) 0.0211(6) Uani 1 1 d . H4 H 0.3721 0.9310 0.7377 0.025 Uiso 1 1 calc R N3 N 0.3608(4) 0.6902(2) 0.6253(3) 0.0140(6) Uani 1 1 d . N2 N 0.8625(5) 0.1237(3) 0.2169(3) 0.0260(7) Uani 1 1 d . H2 H 0.8380 0.0482 0.2000 0.031 Uiso 1 1 calc R C1 C 0.9225(5) 0.1662(3) 0.3220(4) 0.0220(7) Uani 1 1 d . H1 H 0.9461 0.1206 0.3911 0.026 Uiso 1 1 calc R C6 C 0.7781(5) 0.5442(3) 0.3997(3) 0.0176(7) Uani 1 1 d . H6 H 0.8546 0.5832 0.3505 0.021 Uiso 1 1 calc R C10 C 0.3377(5) 0.8077(3) 0.6165(3) 0.0183(7) Uani 1 1 d . H10 H 0.2993 0.8508 0.5472 0.022 Uiso 1 1 calc R C8 C 0.5031(5) 0.5445(3) 0.5014(3) 0.0156(6) Uani 1 1 d . C4 C 1.0003(5) 0.3674(3) 0.4098(3) 0.0198(7) Uani 1 1 d . H4A H 1.0905 0.4269 0.3861 0.024 Uiso 1 1 calc R H4B H 1.0651 0.3227 0.4769 0.024 Uiso 1 1 calc R C7 C 0.6148(5) 0.5998(3) 0.4272(3) 0.0190(7) Uani 1 1 d . H7 H 0.5793 0.6758 0.3952 0.023 Uiso 1 1 calc R C11 C 0.4283(5) 0.7657(3) 0.8001(3) 0.0225(7) Uani 1 1 d . H11 H 0.4641 0.7750 0.8810 0.027 Uiso 1 1 calc R C9 C 0.3242(5) 0.6037(3) 0.5296(3) 0.0177(7) Uani 1 1 d . H9A H 0.2618 0.6454 0.4600 0.021 Uiso 1 1 calc R H9B H 0.2361 0.5415 0.5507 0.021 Uiso 1 1 calc R C12 C 0.4172(5) 0.6619(3) 0.7399(3) 0.0193(7) Uani 1 1 d . H12 H 0.4434 0.5842 0.7707 0.023 Uiso 1 1 calc R C5 C 0.8294(5) 0.4312(3) 0.4445(3) 0.0163(6) Uani 1 1 d . C13 C 0.5575(5) 0.4325(3) 0.5478(3) 0.0202(7) Uani 1 1 d . H13 H 0.4832 0.3942 0.5988 0.024 Uiso 1 1 calc R C2 C 0.8448(5) 0.2161(3) 0.1390(3) 0.0246(8) Uani 1 1 d . H2A H 0.8051 0.2104 0.0581 0.030 Uiso 1 1 calc R C14 C 0.7196(5) 0.3772(3) 0.5196(3) 0.0201(7) Uani 1 1 d . H14 H 0.7558 0.3015 0.5520 0.024 Uiso 1 1 calc R C3 C 0.8946(6) 0.3163(3) 0.1992(4) 0.0225(7) Uani 1 1 d . H3 H 0.8959 0.3950 0.1689 0.027 Uiso 1 1 calc R Cu1 Cu 0.21550(6) 0.18741(4) 0.75236(4) 0.01699(18) Uani 1 1 d . Cl1 Cl 0.15636(11) 0.38228(6) 0.71749(7) 0.0200(2) Uani 1 1 d . Cl2 Cl 0.46228(11) 0.09142(7) 0.85741(7) 0.0208(2) Uani 1 1 d . Cl3 Cl -0.00281(11) 0.15133(8) 0.86838(8) 0.0246(2) Uani 1 1 d . Cl4 Cl 0.27341(13) 0.12418(8) 0.57764(7) 0.0263(2) Uani 1 1 d . O1 O 0.7307(5) 0.0949(3) 0.6345(3) 0.0396(7) Uani 1 1 d . H1A H 0.6193 0.1152 0.6091 0.059 Uiso 1 1 d R H1B H 0.7804 0.1392 0.6895 0.059 Uiso 1 1 d R 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 N1 0.0128(12) 0.0138(12) 0.0234(14) -0.0027(12) 0.0021(11) 0.0020(11) N4 0.0211(14) 0.0117(13) 0.0303(17) -0.0042(12) 0.0021(12) 0.0020(11) N3 0.0124(12) 0.0116(12) 0.0181(15) -0.0003(10) 0.0020(11) 0.0008(9) N2 0.0235(15) 0.0170(14) 0.0374(18) -0.0093(13) 0.0045(13) -0.0002(12) C1 0.0198(17) 0.0151(15) 0.0305(19) -0.0008(14) 0.0015(14) 0.0017(13) C6 0.0190(16) 0.0116(14) 0.0226(17) -0.0004(13) 0.0038(13) -0.0016(12) C10 0.0191(17) 0.0111(15) 0.0249(18) 0.0005(12) 0.0032(13) 0.0030(12) C8 0.0161(15) 0.0112(14) 0.0191(17) -0.0050(12) 0.0007(13) 0.0000(12) C4 0.0150(15) 0.0172(15) 0.0261(19) -0.0059(13) -0.0008(13) 0.0013(13) C7 0.0217(18) 0.0086(15) 0.0266(18) -0.0003(12) 0.0027(14) 0.0018(12) C11 0.0225(17) 0.0251(19) 0.0195(18) -0.0057(14) 0.0012(14) 0.0008(14) C9 0.0166(15) 0.0167(15) 0.0192(17) -0.0038(13) -0.0002(13) -0.0004(12) C12 0.0209(17) 0.0164(15) 0.0201(17) 0.0022(13) 0.0012(13) 0.0048(13) C5 0.0143(15) 0.0098(14) 0.0238(16) -0.0055(12) -0.0010(13) -0.0001(12) C13 0.0235(17) 0.0150(15) 0.0231(17) 0.0015(13) 0.0071(13) -0.0024(14) C2 0.0232(17) 0.0307(19) 0.0203(18) -0.0045(15) 0.0039(14) 0.0022(15) C14 0.0213(18) 0.0118(15) 0.0267(19) 0.0012(13) 0.0020(14) 0.0035(12) C3 0.0226(18) 0.0210(17) 0.0247(18) -0.0008(13) 0.0059(14) 0.0016(13) Cu1 0.0190(3) 0.0121(2) 0.0203(3) -0.00038(18) 0.00437(17) 0.00238(17) Cl1 0.0239(4) 0.0121(3) 0.0245(4) 0.0015(3) 0.0056(3) 0.0033(3) Cl2 0.0212(4) 0.0152(3) 0.0247(4) -0.0035(3) -0.0014(3) 0.0028(3) Cl3 0.0215(4) 0.0254(4) 0.0282(4) 0.0000(3) 0.0082(3) -0.0036(3) Cl4 0.0346(5) 0.0241(4) 0.0202(4) -0.0030(3) 0.0038(3) 0.0110(4) O1 0.0325(15) 0.0300(14) 0.055(2) 0.0161(14) 0.0026(14) 0.0045(12) 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' Cu Cu -1.9646 0.5888 '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 C1 N1 C4 126.0(3) C1 N1 C3 108.8(3) C3 N1 C4 125.1(3) C10 N4 H4 125.1 C10 N4 C11 109.8(3) C11 N4 H4 125.1 C10 N3 C9 125.7(3) C10 N3 C12 108.6(3) C12 N3 C9 125.6(3) C1 N2 H2 125.3 C1 N2 C2 109.4(3) C2 N2 H2 125.3 N1 C1 N2 107.8(3) N1 C1 H1 126.1 N2 C1 H1 126.1 C7 C6 H6 119.9 C7 C6 C5 120.1(3) C5 C6 H6 119.9 N4 C10 N3 108.1(3) N4 C10 H10 126.0 N3 C10 H10 126.0 C7 C8 C9 120.6(3) C7 C8 C13 119.0(3) C13 C8 C9 120.4(3) N1 C4 H4A 109.5 N1 C4 H4B 109.5 N1 C4 C5 110.8(3) H4A C4 H4B 108.1 C5 C4 H4A 109.5 C5 C4 H4B 109.5 C6 C7 C8 120.5(3) C6 C7 H7 119.7 C8 C7 H7 119.7 N4 C11 H11 126.8 C12 C11 N4 106.4(3) C12 C11 H11 126.8 N3 C9 C8 112.6(3) N3 C9 H9A 109.1 N3 C9 H9B 109.1 C8 C9 H9A 109.1 C8 C9 H9B 109.1 H9A C9 H9B 107.8 N3 C12 H12 126.4 C11 C12 N3 107.2(3) C11 C12 H12 126.4 C6 C5 C4 120.4(3) C14 C5 C6 119.2(3) C14 C5 C4 120.4(3) C8 C13 H13 119.9 C14 C13 C8 120.2(3) C14 C13 H13 119.9 N2 C2 H2A 126.6 C3 C2 N2 106.7(3) C3 C2 H2A 126.6 C5 C14 H14 119.6 C13 C14 C5 120.9(3) C13 C14 H14 119.6 N1 C3 H3 126.4 C2 C3 N1 107.3(3) C2 C3 H3 126.4 Cl1 Cu1 Cl2 131.96(4) Cl1 Cu1 Cl4 101.18(4) Cl3 Cu1 Cl1 99.01(3) Cl3 Cu1 Cl2 97.95(4) Cl3 Cu1 Cl4 136.14(4) Cl4 Cu1 Cl2 96.77(3) H1A O1 H1B 112.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C1 1.329(5) N1 C4 1.483(4) N1 C3 1.377(5) N4 H4 0.8800 N4 C10 1.325(5) N4 C11 1.369(5) N3 C10 1.328(4) N3 C9 1.475(4) N3 C12 1.380(5) N2 H2 0.8800 N2 C1 1.333(5) N2 C2 1.372(5) C1 H1 0.9500 C6 H6 0.9500 C6 C7 1.393(5) C6 C5 1.399(5) C10 H10 0.9500 C8 C7 1.397(5) C8 C9 1.511(4) C8 C13 1.400(5) C4 H4A 0.9900 C4 H4B 0.9900 C4 C5 1.512(5) C7 H7 0.9500 C11 H11 0.9500 C11 C12 1.355(5) C9 H9A 0.9900 C9 H9B 0.9900 C12 H12 0.9500 C5 C14 1.389(5) C13 H13 0.9500 C13 C14 1.388(5) C2 H2A 0.9500 C2 C3 1.347(6) C14 H14 0.9500 C3 H3 0.9500 Cu1 Cl1 2.2483(8) Cu1 Cl2 2.2738(9) Cu1 Cl3 2.2320(9) Cu1 Cl4 2.2489(10) O1 H1A 0.8402 O1 H1B 0.8509 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 N1 C4 C5 C6 -95.5(4) N1 C4 C5 C14 83.3(4) N4 C11 C12 N3 0.3(4) N2 C2 C3 N1 0.4(4) C1 N1 C4 C5 -100.3(4) C1 N1 C3 C2 -0.4(4) C1 N2 C2 C3 -0.3(4) C6 C5 C14 C13 1.8(5) C10 N4 C11 C12 -0.3(4) C10 N3 C9 C8 112.9(4) C10 N3 C12 C11 -0.2(4) C8 C13 C14 C5 -0.5(5) C4 N1 C1 N2 177.4(3) C4 N1 C3 C2 -177.6(3) C4 C5 C14 C13 -177.0(3) C7 C6 C5 C4 176.6(3) C7 C6 C5 C14 -2.2(5) C7 C8 C9 N3 -84.7(4) C7 C8 C13 C14 -0.4(5) C11 N4 C10 N3 0.2(4) C9 N3 C10 N4 177.6(3) C9 N3 C12 C11 -177.8(3) C9 C8 C7 C6 -178.9(3) C9 C8 C13 C14 178.5(3) C12 N3 C10 N4 0.0(4) C12 N3 C9 C8 -69.9(4) C5 C6 C7 C8 1.3(5) C13 C8 C7 C6 0.0(5) C13 C8 C9 N3 96.4(4) C2 N2 C1 N1 0.1(4) C3 N1 C1 N2 0.2(4) C3 N1 C4 C5 76.5(4) loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.951(18) 2 0.049(18)