#------------------------------------------------------------------------------ #$Date: 2019-07-12 03:15:06 +0300 (Fri, 12 Jul 2019) $ #$Revision: 216965 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/20/1552086.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_1552086 loop_ _publ_author_name 'Pichon, Delphine' 'Soleilhavoup, Michele' 'Morvan, Jennifer' 'Junor, Glen P.' 'Vives, Thomas' 'Cr\'evisy, Christophe' 'Lavallo, Vincent' 'Campagne, Jean-Marc' 'Mauduit, Marc' 'Jazzar, Rodolphe' 'Bertrand, Guy' _publ_section_title ; The debut of chiral cyclic (alkyl)(amino)carbenes (CAACs) in enantioselective catalysis ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC02810B _journal_year 2019 _chemical_absolute_configuration syn _chemical_formula_moiety 'C44 H71 Cl Cu N, C2 H3 N' _chemical_formula_sum 'C46 H74 Cl Cu N2' _chemical_formula_weight 754.06 _chemical_name_systematic CholestCAACCuCl _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' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2019-05-28 _audit_creation_method ; Olex2 1.2 (compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-28 deposited with the CCDC. 2019-07-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.269(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.2490(13) _cell_length_b 12.0899(15) _cell_length_c 17.740(2) _cell_measurement_reflns_used 961 _cell_measurement_temperature 100.15 _cell_measurement_theta_max 26.18 _cell_measurement_theta_min 2.60 _cell_volume 2197.6(5) _computing_cell_refinement 'SAINT v7.68A (Bruker, 2009)' _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 100.15 _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.979 _diffrn_measured_fraction_theta_max 0.832 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX2 area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_unetI/netI 0.0696 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.832 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 13409 _diffrn_reflns_point_group_measured_fraction_full 0.766 _diffrn_reflns_point_group_measured_fraction_max 0.589 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 33.543 _diffrn_reflns_theta_min 5.188 _exptl_absorpt_coefficient_mu 0.589 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0536 before and 0.0447 after correction. The Ratio of minimum to maximum transmission is 0.8577. The \l/2 correction factor is 0.0015.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.140 _exptl_crystal_description plate _exptl_crystal_F_000 820 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile/diethyl ether' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.496 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.052 _refine_ls_abs_structure_details ; Flack x determined using 2091 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.012(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.947 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 463 _refine_ls_number_reflns 10194 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.947 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0324 _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^)+(0.0160P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0668 _refine_ls_wR_factor_ref 0.0695 _reflns_Friedel_coverage 0.362 _reflns_Friedel_fraction_full 0.530 _reflns_Friedel_fraction_max 0.326 _reflns_number_gt 8579 _reflns_number_total 10194 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc02810b2.cif _cod_data_source_block cholescaaccucl _cod_database_code 1552086 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.943 _shelx_estimated_absorpt_t_min 0.867 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C8(H8), C12(H12), C15(H15), C16(H16), C19(H19), C27(H27), C30(H30), C37(H37), C41(H41) 2.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A, H13B), C14(H14A,H14B), C17(H17A,H17B), C18(H18A,H18B), C20(H20A,H20B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B) 2.c Aromatic/amide H refined with riding coordinates: C23(H23), C24(H24), C25(H25) 2.d Idealised Me refined as rotating group: C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,H32B, H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A, H36B,H36C), C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C2A(H2AA,H2AB,H2AC) ; _shelx_res_file ; TITL CholesCAACCuCl in P2(1) cholescaaccucl.res created by SHELXL-2018/3 at 12:55:39 on 28-May-2019 CELL 0.71073 10.249 12.0899 17.7402 90 91.269 90 ZERR 2 0.0013 0.0015 0.0022 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Cl Cu N UNIT 92 148 2 2 4 L.S. 15 PLAN 5 SIZE 0.25 0.15 0.1 TEMP -173 fmap 2 acta 50 MERG 2 REM REM REM WGHT 0.016000 FVAR 0.22309 CU1 4 0.414769 0.334231 0.645613 11.00000 0.01132 0.01578 = 0.01715 0.00076 -0.00101 -0.00074 CL1 3 0.619946 0.339268 0.655434 11.00000 0.01223 0.03313 = 0.03286 0.01221 -0.00246 -0.00190 N1 5 0.165480 0.247419 0.609974 11.00000 0.01091 0.01353 = 0.01227 0.00037 -0.00057 0.00071 C1 1 0.231884 0.332981 0.634204 11.00000 0.01371 0.01227 = 0.00911 0.00144 -0.00140 -0.00019 C2 1 0.017282 0.263567 0.601526 11.00000 0.01041 0.01469 = 0.02059 -0.00133 0.00021 -0.00013 C3 1 0.010136 0.389394 0.609089 11.00000 0.01251 0.01656 = 0.01772 -0.00085 -0.00392 0.00192 AFIX 23 H3A 2 -0.066407 0.410851 0.638865 11.00000 -1.20000 H3B 2 0.002034 0.424256 0.558707 11.00000 -1.20000 AFIX 0 C4 1 0.137727 0.426896 0.649553 11.00000 0.01304 0.01250 = 0.01431 0.00048 -0.00209 0.00022 C5 1 0.186199 0.539317 0.620411 11.00000 0.01871 0.01328 = 0.01515 0.00076 -0.00151 -0.00029 AFIX 23 H5A 2 0.210123 0.530976 0.566949 11.00000 -1.20000 H5B 2 0.113571 0.593158 0.622342 11.00000 -1.20000 AFIX 0 C6 1 0.303223 0.586325 0.664499 11.00000 0.01773 0.01339 = 0.01417 0.00179 0.00047 -0.00153 AFIX 23 H6A 2 0.322493 0.661034 0.644793 11.00000 -1.20000 H6B 2 0.380115 0.539080 0.655226 11.00000 -1.20000 AFIX 0 C7 1 0.284343 0.594683 0.750512 11.00000 0.01740 0.01205 = 0.01236 -0.00119 0.00098 -0.00234 C8 1 0.417192 0.618977 0.790399 11.00000 0.01709 0.01342 = 0.01189 -0.00018 0.00092 -0.00178 AFIX 13 H8 2 0.477306 0.558158 0.775230 11.00000 -1.20000 AFIX 0 C9 1 0.482310 0.727797 0.765871 11.00000 0.02520 0.01788 = 0.01249 0.00222 -0.00037 -0.00766 AFIX 23 H9A 2 0.487762 0.728974 0.710230 11.00000 -1.20000 H9B 2 0.427329 0.790921 0.781142 11.00000 -1.20000 AFIX 0 C10 1 0.619737 0.741786 0.800665 11.00000 0.02233 0.02170 = 0.01257 0.00044 0.00189 -0.00729 AFIX 23 H10A 2 0.677173 0.682969 0.781227 11.00000 -1.20000 H10B 2 0.655728 0.813977 0.784948 11.00000 -1.20000 AFIX 0 C11 1 0.619967 0.736149 0.886916 11.00000 0.01742 0.01524 = 0.01358 -0.00136 0.00220 -0.00429 C12 1 0.753866 0.716025 0.927117 11.00000 0.01984 0.02099 = 0.01630 0.00016 0.00111 -0.00099 AFIX 13 H12 2 0.799270 0.657643 0.897585 11.00000 -1.20000 AFIX 0 C13 1 0.716791 0.662345 1.003460 11.00000 0.02260 0.02789 = 0.01700 0.00378 -0.00491 -0.00692 AFIX 23 H13A 2 0.778168 0.601762 1.016611 11.00000 -1.20000 H13B 2 0.720336 0.718110 1.044320 11.00000 -1.20000 AFIX 0 C14 1 0.576566 0.616687 0.993293 11.00000 0.02700 0.02707 = 0.01420 0.00482 -0.00228 -0.00916 AFIX 23 H14A 2 0.571531 0.538583 1.009739 11.00000 -1.20000 H14B 2 0.513637 0.661134 1.022079 11.00000 -1.20000 AFIX 0 C15 1 0.550411 0.627191 0.908638 11.00000 0.02154 0.01561 = 0.01142 -0.00027 -0.00022 -0.00257 AFIX 13 H15 2 0.601877 0.566601 0.885031 11.00000 -1.20000 AFIX 0 C16 1 0.411533 0.614256 0.877232 11.00000 0.02084 0.01518 = 0.01215 0.00098 0.00096 -0.00367 AFIX 13 H16 2 0.357380 0.677326 0.895294 11.00000 -1.20000 AFIX 0 C17 1 0.351620 0.505434 0.904304 11.00000 0.02549 0.01766 = 0.01290 0.00120 0.00051 -0.00568 AFIX 23 H17A 2 0.414631 0.444688 0.896396 11.00000 -1.20000 H17B 2 0.336321 0.510740 0.959090 11.00000 -1.20000 AFIX 0 C18 1 0.223116 0.477093 0.863604 11.00000 0.02249 0.01790 = 0.01422 0.00151 0.00206 -0.00603 AFIX 23 H18A 2 0.193904 0.402606 0.879127 11.00000 -1.20000 H18B 2 0.155285 0.531105 0.877717 11.00000 -1.20000 AFIX 0 C19 1 0.240431 0.479522 0.778521 11.00000 0.01768 0.01092 = 0.01371 -0.00023 0.00215 -0.00128 AFIX 13 H19 2 0.313097 0.427138 0.767556 11.00000 -1.20000 AFIX 0 C20 1 0.119817 0.435947 0.736113 11.00000 0.01685 0.01329 = 0.01625 -0.00137 0.00247 -0.00013 AFIX 23 H20A 2 0.045354 0.485718 0.745838 11.00000 -1.20000 H20B 2 0.097836 0.361972 0.756117 11.00000 -1.20000 AFIX 0 C21 1 0.222518 0.138927 0.597942 11.00000 0.01160 0.01163 = 0.01806 -0.00147 0.00012 -0.00213 C22 1 0.241940 0.068198 0.660028 11.00000 0.01361 0.01518 = 0.01589 0.00093 0.00013 -0.00046 C23 1 0.281521 -0.040022 0.645088 11.00000 0.02028 0.01491 = 0.02350 0.00496 -0.00158 0.00025 AFIX 43 H23 2 0.292853 -0.090492 0.685753 11.00000 -1.20000 AFIX 0 C24 1 0.304594 -0.075374 0.572421 11.00000 0.02200 0.01295 = 0.02983 -0.00298 0.00037 0.00230 AFIX 43 H24 2 0.326791 -0.150414 0.563321 11.00000 -1.20000 AFIX 0 C25 1 0.295359 -0.001548 0.513065 11.00000 0.02098 0.01894 = 0.02035 -0.00526 0.00248 0.00093 AFIX 43 H25 2 0.315957 -0.025483 0.463729 11.00000 -1.20000 AFIX 0 C26 1 0.256183 0.107771 0.524511 11.00000 0.01360 0.01686 = 0.01513 -0.00189 0.00123 -0.00126 C27 1 0.231559 0.105209 0.741781 11.00000 0.02250 0.01853 = 0.01469 0.00416 0.00066 -0.00067 AFIX 13 H27 2 0.192290 0.180928 0.741812 11.00000 -1.20000 AFIX 0 C28 1 0.144346 0.029651 0.788283 11.00000 0.03186 0.02948 = 0.02080 0.00688 0.00397 -0.00565 AFIX 137 H28A 2 0.060930 0.018349 0.761311 11.00000 -1.50000 H28B 2 0.128627 0.064098 0.837256 11.00000 -1.50000 H28C 2 0.187687 -0.041833 0.796031 11.00000 -1.50000 AFIX 0 C29 1 0.367984 0.113114 0.778624 11.00000 0.02794 0.03362 = 0.01716 0.00382 -0.00466 -0.00225 AFIX 137 H29A 2 0.408357 0.039638 0.779819 11.00000 -1.50000 H29B 2 0.360844 0.141131 0.830206 11.00000 -1.50000 H29C 2 0.421949 0.163627 0.749397 11.00000 -1.50000 AFIX 0 C30 1 0.264585 0.191168 0.460445 11.00000 0.02148 0.01899 = 0.01635 -0.00018 0.00424 -0.00094 AFIX 13 H30 2 0.215278 0.258843 0.475286 11.00000 -1.20000 AFIX 0 C31 1 0.408758 0.223935 0.451550 11.00000 0.02530 0.02771 = 0.02345 0.00137 0.00730 -0.00503 AFIX 137 H31A 2 0.443328 0.253296 0.499454 11.00000 -1.50000 H31B 2 0.415309 0.280616 0.412324 11.00000 -1.50000 H31C 2 0.459307 0.158728 0.437216 11.00000 -1.50000 AFIX 0 C32 1 0.207046 0.150104 0.385502 11.00000 0.03024 0.02768 = 0.01597 -0.00125 -0.00147 -0.00428 AFIX 137 H32A 2 0.258107 0.087071 0.367809 11.00000 -1.50000 H32B 2 0.209664 0.209782 0.348182 11.00000 -1.50000 H32C 2 0.116402 0.127078 0.392369 11.00000 -1.50000 AFIX 0 C33 1 -0.050101 0.200610 0.665164 11.00000 0.01231 0.01956 = 0.02284 -0.00214 0.00144 -0.00315 AFIX 137 H33A 2 -0.016631 0.227206 0.714063 11.00000 -1.50000 H33B 2 -0.032118 0.121325 0.660470 11.00000 -1.50000 H33C 2 -0.144491 0.213184 0.661510 11.00000 -1.50000 AFIX 0 C34 1 -0.034874 0.221942 0.526436 11.00000 0.01769 0.02299 = 0.01987 -0.00476 -0.00545 -0.00051 AFIX 137 H34A 2 -0.015953 0.142816 0.521739 11.00000 -1.50000 H34B 2 0.006947 0.262361 0.485626 11.00000 -1.50000 H34C 2 -0.129451 0.233646 0.523228 11.00000 -1.50000 AFIX 0 C35 1 0.182735 0.685150 0.766980 11.00000 0.02157 0.01394 = 0.02118 -0.00154 0.00148 0.00055 AFIX 137 H35A 2 0.096558 0.661134 0.748377 11.00000 -1.50000 H35B 2 0.207139 0.753829 0.741557 11.00000 -1.50000 H35C 2 0.179957 0.697959 0.821469 11.00000 -1.50000 AFIX 0 C36 1 0.552780 0.838529 0.919594 11.00000 0.02133 0.01784 = 0.02101 -0.00305 0.00016 -0.00362 AFIX 137 H36A 2 0.462759 0.842642 0.899994 11.00000 -1.50000 H36B 2 0.600275 0.905224 0.904930 11.00000 -1.50000 H36C 2 0.552445 0.833033 0.974704 11.00000 -1.50000 AFIX 0 C37 1 0.851790 0.811754 0.938101 11.00000 0.01851 0.02701 = 0.01775 -0.00152 0.00123 -0.00545 AFIX 13 H37 2 0.813597 0.866199 0.973864 11.00000 -1.20000 AFIX 0 C38 1 0.978296 0.764909 0.974685 11.00000 0.02037 0.03832 = 0.02121 0.00026 -0.00002 -0.00218 AFIX 23 H38A 2 0.955816 0.729789 1.023109 11.00000 -1.20000 H38B 2 1.011792 0.706045 0.941487 11.00000 -1.20000 AFIX 0 C39 1 1.088285 0.847782 0.989939 11.00000 0.02431 0.05195 = 0.02354 0.00941 -0.00130 -0.01255 AFIX 23 H39A 2 1.054440 0.910234 1.019849 11.00000 -1.20000 H39B 2 1.118474 0.877707 0.941393 11.00000 -1.20000 AFIX 0 C40 1 1.204134 0.794902 1.032716 11.00000 0.01825 0.06273 = 0.02139 -0.00104 0.00104 -0.00363 AFIX 23 H40A 2 1.224107 0.723227 1.008574 11.00000 -1.20000 H40B 2 1.281301 0.843230 1.027149 11.00000 -1.20000 AFIX 0 C41 1 1.184172 0.774790 1.116626 11.00000 0.01836 0.04020 = 0.02413 0.00047 -0.00098 -0.00212 AFIX 13 H41 2 1.097419 0.738515 1.122971 11.00000 -1.20000 AFIX 0 C42 1 1.290193 0.698145 1.148864 11.00000 0.05548 0.05222 = 0.03401 -0.00807 -0.00826 0.01976 AFIX 137 H42A 2 1.286393 0.626946 1.122501 11.00000 -1.50000 H42B 2 1.276094 0.686434 1.202736 11.00000 -1.50000 H42C 2 1.376029 0.731942 1.142013 11.00000 -1.50000 AFIX 0 C43 1 1.185710 0.883649 1.160809 11.00000 0.03275 0.03946 = 0.02879 0.00290 0.00359 0.00051 AFIX 137 H43A 2 1.270989 0.919332 1.156060 11.00000 -1.50000 H43B 2 1.169736 0.868538 1.214089 11.00000 -1.50000 H43C 2 1.117387 0.932724 1.140548 11.00000 -1.50000 AFIX 0 C44 1 0.881886 0.872516 0.864936 11.00000 0.02410 0.04113 = 0.02321 0.00623 -0.00195 -0.01300 AFIX 137 H44A 2 0.915509 0.819811 0.828159 11.00000 -1.50000 H44B 2 0.947493 0.929868 0.875161 11.00000 -1.50000 H44C 2 0.801950 0.906819 0.844587 11.00000 -1.50000 AFIX 0 N1A 5 0.834457 0.945705 0.586637 11.00000 0.05761 0.03870 = 0.09478 -0.02906 0.01726 -0.01452 C1A 1 0.742498 0.984710 0.606048 11.00000 0.04051 0.02934 = 0.05717 -0.01405 -0.00024 -0.01402 C2A 1 0.624244 1.035782 0.631852 11.00000 0.04200 0.05016 = 0.25730 -0.04177 0.02405 -0.01213 AFIX 137 H2AA 2 0.580376 0.985510 0.666446 11.00000 -1.50000 H2AB 2 0.566255 1.051566 0.588518 11.00000 -1.50000 H2AC 2 0.645830 1.104938 0.658110 11.00000 -1.50000 AFIX 0 HKLF 4 REM CholesCAACCuCl in P2(1) REM wR2 = 0.0695, GooF = S = 0.947, Restrained GooF = 0.947 for all data REM R1 = 0.0324 for 8579 Fo > 4sig(Fo) and 0.0432 for all 10194 data REM 463 parameters refined using 1 restraints END WGHT 0.0163 0.0000 REM Highest difference peak 0.496, deepest hole -0.401, 1-sigma level 0.052 Q1 1 0.3169 0.3248 0.6334 11.00000 0.05 0.39 Q2 1 0.6248 1.0217 0.6474 11.00000 0.05 0.36 Q3 1 0.3695 0.3628 0.6085 11.00000 0.05 0.34 Q4 1 0.3632 0.3319 0.6029 11.00000 0.05 0.34 Q5 1 0.6246 1.0585 0.5815 11.00000 0.05 0.32 ; _shelx_res_checksum 33275 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn Cu1 Cu 0.41477(2) 0.33423(2) 0.64561(2) 0.01477(6) Uani 1 1 d . Cl1 Cl 0.61995(4) 0.33927(6) 0.65543(3) 0.02612(11) Uani 1 1 d . N1 N 0.16548(16) 0.24742(13) 0.60997(10) 0.0122(3) Uani 1 1 d . C1 C 0.23188(16) 0.3330(2) 0.63420(9) 0.0117(3) Uani 1 1 d . C2 C 0.0173(2) 0.26357(18) 0.60153(14) 0.0152(5) Uani 1 1 d . C3 C 0.0101(2) 0.38939(18) 0.60909(14) 0.0157(5) Uani 1 1 d . H3A H -0.066407 0.410851 0.638865 0.019 Uiso 1 1 calc R H3B H 0.002034 0.424256 0.558707 0.019 Uiso 1 1 calc R C4 C 0.13773(19) 0.42690(16) 0.64955(12) 0.0133(4) Uani 1 1 d . C5 C 0.1862(2) 0.53932(17) 0.62041(13) 0.0157(4) Uani 1 1 d . H5A H 0.210123 0.530976 0.566949 0.019 Uiso 1 1 calc R H5B H 0.113571 0.593158 0.622342 0.019 Uiso 1 1 calc R C6 C 0.3032(2) 0.58632(16) 0.66450(12) 0.0151(4) Uani 1 1 d . H6A H 0.322493 0.661034 0.644793 0.018 Uiso 1 1 calc R H6B H 0.380115 0.539080 0.655226 0.018 Uiso 1 1 calc R C7 C 0.2843(2) 0.59468(16) 0.75051(12) 0.0139(4) Uani 1 1 d . C8 C 0.4172(2) 0.61898(16) 0.79040(12) 0.0141(4) Uani 1 1 d . H8 H 0.477306 0.558158 0.775230 0.017 Uiso 1 1 calc R C9 C 0.4823(2) 0.72780(18) 0.76587(12) 0.0185(4) Uani 1 1 d . H9A H 0.487762 0.728974 0.710230 0.022 Uiso 1 1 calc R H9B H 0.427329 0.790921 0.781142 0.022 Uiso 1 1 calc R C10 C 0.6197(2) 0.74179(18) 0.80067(12) 0.0188(4) Uani 1 1 d . H10A H 0.677173 0.682969 0.781227 0.023 Uiso 1 1 calc R H10B H 0.655728 0.813977 0.784948 0.023 Uiso 1 1 calc R C11 C 0.6200(2) 0.73615(16) 0.88692(12) 0.0154(4) Uani 1 1 d . C12 C 0.7539(2) 0.71602(18) 0.92712(12) 0.0190(4) Uani 1 1 d . H12 H 0.799270 0.657643 0.897585 0.023 Uiso 1 1 calc R C13 C 0.7168(2) 0.66235(19) 1.00346(13) 0.0226(5) Uani 1 1 d . H13A H 0.778168 0.601762 1.016611 0.027 Uiso 1 1 calc R H13B H 0.720336 0.718110 1.044320 0.027 Uiso 1 1 calc R C14 C 0.5766(2) 0.6167(2) 0.99329(12) 0.0228(5) Uani 1 1 d . H14A H 0.571531 0.538583 1.009739 0.027 Uiso 1 1 calc R H14B H 0.513637 0.661134 1.022079 0.027 Uiso 1 1 calc R C15 C 0.5504(2) 0.62719(17) 0.90864(12) 0.0162(4) Uani 1 1 d . H15 H 0.601877 0.566601 0.885031 0.019 Uiso 1 1 calc R C16 C 0.4115(2) 0.61426(17) 0.87723(12) 0.0160(4) Uani 1 1 d . H16 H 0.357380 0.677326 0.895294 0.019 Uiso 1 1 calc R C17 C 0.3516(2) 0.50543(17) 0.90430(12) 0.0187(4) Uani 1 1 d . H17A H 0.414631 0.444688 0.896396 0.022 Uiso 1 1 calc R H17B H 0.336321 0.510740 0.959090 0.022 Uiso 1 1 calc R C18 C 0.2231(2) 0.47709(17) 0.86360(12) 0.0182(4) Uani 1 1 d . H18A H 0.193904 0.402606 0.879127 0.022 Uiso 1 1 calc R H18B H 0.155285 0.531105 0.877717 0.022 Uiso 1 1 calc R C19 C 0.2404(2) 0.47952(15) 0.77852(12) 0.0141(4) Uani 1 1 d . H19 H 0.313097 0.427138 0.767556 0.017 Uiso 1 1 calc R C20 C 0.11982(19) 0.43595(16) 0.73611(12) 0.0154(4) Uani 1 1 d . H20A H 0.045354 0.485718 0.745838 0.019 Uiso 1 1 calc R H20B H 0.097836 0.361972 0.756117 0.019 Uiso 1 1 calc R C21 C 0.2225(2) 0.13893(16) 0.59794(12) 0.0138(4) Uani 1 1 d . C22 C 0.2419(2) 0.06820(16) 0.66003(12) 0.0149(4) Uani 1 1 d . C23 C 0.2815(2) -0.04002(17) 0.64509(13) 0.0196(4) Uani 1 1 d . H23 H 0.292853 -0.090492 0.685753 0.024 Uiso 1 1 calc R C24 C 0.3046(2) -0.07537(17) 0.57242(14) 0.0216(5) Uani 1 1 d . H24 H 0.326791 -0.150414 0.563321 0.026 Uiso 1 1 calc R C25 C 0.2954(2) -0.00155(17) 0.51306(13) 0.0201(5) Uani 1 1 d . H25 H 0.315957 -0.025483 0.463729 0.024 Uiso 1 1 calc R C26 C 0.25618(19) 0.10777(17) 0.52451(12) 0.0152(4) Uani 1 1 d . C27 C 0.2316(2) 0.10521(18) 0.74178(12) 0.0186(4) Uani 1 1 d . H27 H 0.192290 0.180928 0.741812 0.022 Uiso 1 1 calc R C28 C 0.1443(3) 0.0297(2) 0.78828(14) 0.0273(5) Uani 1 1 d . H28A H 0.060930 0.018349 0.761311 0.041 Uiso 1 1 calc GR H28B H 0.128627 0.064098 0.837256 0.041 Uiso 1 1 calc GR H28C H 0.187687 -0.041833 0.796031 0.041 Uiso 1 1 calc GR C29 C 0.3680(2) 0.1131(2) 0.77862(13) 0.0263(5) Uani 1 1 d . H29A H 0.408357 0.039638 0.779819 0.039 Uiso 1 1 calc GR H29B H 0.360844 0.141131 0.830206 0.039 Uiso 1 1 calc GR H29C H 0.421949 0.163627 0.749397 0.039 Uiso 1 1 calc GR C30 C 0.2646(2) 0.19117(18) 0.46044(13) 0.0189(4) Uani 1 1 d . H30 H 0.215278 0.258843 0.475286 0.023 Uiso 1 1 calc R C31 C 0.4088(2) 0.2239(2) 0.45155(14) 0.0254(5) Uani 1 1 d . H31A H 0.443328 0.253296 0.499454 0.038 Uiso 1 1 calc GR H31B H 0.415309 0.280616 0.412324 0.038 Uiso 1 1 calc GR H31C H 0.459307 0.158728 0.437216 0.038 Uiso 1 1 calc GR C32 C 0.2070(3) 0.1501(2) 0.38550(14) 0.0247(5) Uani 1 1 d . H32A H 0.258107 0.087071 0.367809 0.037 Uiso 1 1 calc GR H32B H 0.209664 0.209782 0.348182 0.037 Uiso 1 1 calc GR H32C H 0.116402 0.127078 0.392369 0.037 Uiso 1 1 calc GR C33 C -0.0501(2) 0.20061(18) 0.66516(13) 0.0182(4) Uani 1 1 d . H33A H -0.016631 0.227206 0.714063 0.027 Uiso 1 1 calc GR H33B H -0.032118 0.121325 0.660470 0.027 Uiso 1 1 calc GR H33C H -0.144491 0.213184 0.661510 0.027 Uiso 1 1 calc GR C34 C -0.0349(2) 0.22194(19) 0.52644(13) 0.0203(4) Uani 1 1 d . H34A H -0.015953 0.142816 0.521739 0.030 Uiso 1 1 calc GR H34B H 0.006947 0.262361 0.485626 0.030 Uiso 1 1 calc GR H34C H -0.129451 0.233646 0.523228 0.030 Uiso 1 1 calc GR C35 C 0.1827(2) 0.68515(17) 0.76698(13) 0.0189(4) Uani 1 1 d . H35A H 0.096558 0.661134 0.748377 0.028 Uiso 1 1 calc GR H35B H 0.207139 0.753829 0.741557 0.028 Uiso 1 1 calc GR H35C H 0.179957 0.697959 0.821469 0.028 Uiso 1 1 calc GR C36 C 0.55278(18) 0.8385(2) 0.91959(11) 0.0201(4) Uani 1 1 d . H36A H 0.462759 0.842642 0.899994 0.030 Uiso 1 1 calc GR H36B H 0.600275 0.905224 0.904930 0.030 Uiso 1 1 calc GR H36C H 0.552445 0.833033 0.974704 0.030 Uiso 1 1 calc GR C37 C 0.8518(2) 0.81175(18) 0.93810(12) 0.0211(5) Uani 1 1 d . H37 H 0.813597 0.866199 0.973864 0.025 Uiso 1 1 calc R C38 C 0.9783(2) 0.7649(2) 0.97469(14) 0.0266(5) Uani 1 1 d . H38A H 0.955816 0.729789 1.023109 0.032 Uiso 1 1 calc R H38B H 1.011792 0.706045 0.941487 0.032 Uiso 1 1 calc R C39 C 1.0883(2) 0.8478(3) 0.98994(13) 0.0333(6) Uani 1 1 d . H39A H 1.054440 0.910234 1.019849 0.040 Uiso 1 1 calc R H39B H 1.118474 0.877707 0.941393 0.040 Uiso 1 1 calc R C40 C 1.2041(2) 0.7949(3) 1.03272(14) 0.0341(6) Uani 1 1 d . H40A H 1.224107 0.723227 1.008574 0.041 Uiso 1 1 calc R H40B H 1.281301 0.843230 1.027149 0.041 Uiso 1 1 calc R C41 C 1.1842(2) 0.7748(2) 1.11663(15) 0.0276(5) Uani 1 1 d . H41 H 1.097419 0.738515 1.122971 0.033 Uiso 1 1 calc R C42 C 1.2902(3) 0.6981(3) 1.14886(18) 0.0474(8) Uani 1 1 d . H42A H 1.286393 0.626946 1.122501 0.071 Uiso 1 1 calc GR H42B H 1.276094 0.686434 1.202736 0.071 Uiso 1 1 calc GR H42C H 1.376029 0.731942 1.142013 0.071 Uiso 1 1 calc GR C43 C 1.1857(3) 0.8836(2) 1.16081(16) 0.0336(6) Uani 1 1 d . H43A H 1.270989 0.919332 1.156060 0.050 Uiso 1 1 calc GR H43B H 1.169736 0.868538 1.214089 0.050 Uiso 1 1 calc GR H43C H 1.117387 0.932724 1.140548 0.050 Uiso 1 1 calc GR C44 C 0.8819(2) 0.8725(2) 0.86494(14) 0.0295(6) Uani 1 1 d . H44A H 0.915509 0.819811 0.828159 0.044 Uiso 1 1 calc GR H44B H 0.947493 0.929868 0.875161 0.044 Uiso 1 1 calc GR H44C H 0.801950 0.906819 0.844587 0.044 Uiso 1 1 calc GR N1A N 0.8345(3) 0.9457(2) 0.5866(2) 0.0635(9) Uani 1 1 d . C1A C 0.7425(3) 0.9847(2) 0.60605(19) 0.0424(7) Uani 1 1 d . C2A C 0.6242(4) 1.0358(4) 0.6319(4) 0.116(2) Uani 1 1 d . H2AA H 0.580376 0.985510 0.666446 0.174 Uiso 1 1 calc GR H2AB H 0.566255 1.051566 0.588518 0.174 Uiso 1 1 calc GR H2AC H 0.645830 1.104938 0.658110 0.174 Uiso 1 1 calc GR 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 0.01132(10) 0.01578(10) 0.01715(12) 0.00076(13) -0.00101(8) -0.00074(12) Cl1 0.01223(19) 0.0331(3) 0.0329(3) 0.0122(3) -0.00246(18) -0.0019(3) N1 0.0109(7) 0.0135(7) 0.0123(8) 0.0004(7) -0.0006(6) 0.0007(6) C1 0.0137(7) 0.0123(7) 0.0091(8) 0.0014(10) -0.0014(6) -0.0002(10) C2 0.0104(10) 0.0147(9) 0.0206(12) -0.0013(9) 0.0002(9) -0.0001(7) C3 0.0125(10) 0.0166(9) 0.0177(11) -0.0009(9) -0.0039(9) 0.0019(8) C4 0.0130(9) 0.0125(8) 0.0143(10) 0.0005(8) -0.0021(8) 0.0002(7) C5 0.0187(11) 0.0133(9) 0.0152(11) 0.0008(8) -0.0015(8) -0.0003(8) C6 0.0177(10) 0.0134(9) 0.0142(10) 0.0018(8) 0.0005(8) -0.0015(7) C7 0.0174(10) 0.0120(8) 0.0124(10) -0.0012(8) 0.0010(8) -0.0023(7) C8 0.0171(10) 0.0134(8) 0.0119(10) -0.0002(8) 0.0009(8) -0.0018(7) C9 0.0252(11) 0.0179(9) 0.0125(10) 0.0022(8) -0.0004(8) -0.0077(8) C10 0.0223(11) 0.0217(10) 0.0126(10) 0.0004(8) 0.0019(8) -0.0073(8) C11 0.0174(9) 0.0152(9) 0.0136(10) -0.0014(8) 0.0022(8) -0.0043(7) C12 0.0198(10) 0.0210(10) 0.0163(11) 0.0002(9) 0.0011(8) -0.0010(8) C13 0.0226(11) 0.0279(11) 0.0170(11) 0.0038(9) -0.0049(9) -0.0069(9) C14 0.0270(12) 0.0271(11) 0.0142(11) 0.0048(9) -0.0023(9) -0.0092(9) C15 0.0215(10) 0.0156(9) 0.0114(10) -0.0003(8) -0.0002(8) -0.0026(8) C16 0.0208(10) 0.0152(9) 0.0121(10) 0.0010(8) 0.0010(8) -0.0037(8) C17 0.0255(11) 0.0177(9) 0.0129(10) 0.0012(8) 0.0005(8) -0.0057(8) C18 0.0225(11) 0.0179(9) 0.0142(10) 0.0015(8) 0.0021(8) -0.0060(8) C19 0.0177(10) 0.0109(8) 0.0137(10) -0.0002(8) 0.0022(8) -0.0013(7) C20 0.0168(9) 0.0133(8) 0.0162(11) -0.0014(8) 0.0025(8) -0.0001(7) C21 0.0116(9) 0.0116(8) 0.0181(11) -0.0015(8) 0.0001(8) -0.0021(7) C22 0.0136(10) 0.0152(9) 0.0159(11) 0.0009(8) 0.0001(8) -0.0005(7) C23 0.0203(10) 0.0149(9) 0.0235(12) 0.0050(9) -0.0016(9) 0.0002(8) C24 0.0220(11) 0.0129(9) 0.0298(13) -0.0030(9) 0.0004(9) 0.0023(8) C25 0.0210(11) 0.0189(10) 0.0203(12) -0.0053(9) 0.0025(9) 0.0009(8) C26 0.0136(9) 0.0169(9) 0.0151(10) -0.0019(8) 0.0012(8) -0.0013(7) C27 0.0225(11) 0.0185(10) 0.0147(11) 0.0042(9) 0.0007(9) -0.0007(8) C28 0.0319(13) 0.0295(12) 0.0208(12) 0.0069(10) 0.0040(10) -0.0056(10) C29 0.0279(12) 0.0336(12) 0.0172(12) 0.0038(10) -0.0047(9) -0.0022(10) C30 0.0215(11) 0.0190(9) 0.0164(11) -0.0002(9) 0.0042(9) -0.0009(8) C31 0.0253(11) 0.0277(11) 0.0234(12) 0.0014(10) 0.0073(9) -0.0050(9) C32 0.0302(13) 0.0277(12) 0.0160(12) -0.0013(10) -0.0015(10) -0.0043(10) C33 0.0123(9) 0.0196(9) 0.0228(11) -0.0021(9) 0.0014(8) -0.0031(7) C34 0.0177(10) 0.0230(10) 0.0199(11) -0.0048(9) -0.0055(8) -0.0005(8) C35 0.0216(11) 0.0139(9) 0.0212(12) -0.0015(9) 0.0015(9) 0.0005(8) C36 0.0213(9) 0.0178(8) 0.0210(10) -0.0031(12) 0.0002(7) -0.0036(11) C37 0.0185(9) 0.0270(13) 0.0178(10) -0.0015(9) 0.0012(8) -0.0054(8) C38 0.0204(11) 0.0383(13) 0.0212(12) 0.0003(10) 0.0000(9) -0.0022(10) C39 0.0243(10) 0.0520(17) 0.0235(11) 0.0094(14) -0.0013(9) -0.0125(13) C40 0.0183(11) 0.0627(18) 0.0214(12) -0.0010(12) 0.0010(9) -0.0036(11) C41 0.0184(11) 0.0402(14) 0.0241(13) 0.0005(11) -0.0010(10) -0.0021(10) C42 0.055(2) 0.0522(18) 0.0340(17) -0.0081(15) -0.0083(14) 0.0198(16) C43 0.0327(14) 0.0395(14) 0.0288(14) 0.0029(12) 0.0036(11) 0.0005(11) C44 0.0241(11) 0.0411(14) 0.0232(12) 0.0062(10) -0.0019(9) -0.0130(10) N1A 0.0576(19) 0.0387(15) 0.095(3) -0.0291(15) 0.0173(17) -0.0145(13) C1A 0.0405(17) 0.0293(14) 0.057(2) -0.0140(14) -0.0002(15) -0.0140(12) C2A 0.042(2) 0.050(2) 0.257(7) -0.042(3) 0.024(3) -0.0121(19) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 Cu1 Cl1 178.13(7) C1 N1 C2 116.02(16) C1 N1 C21 123.70(17) C21 N1 C2 120.04(16) N1 C1 Cu1 123.55(17) N1 C1 C4 108.83(15) C4 C1 Cu1 127.62(17) N1 C2 C33 108.95(18) C3 C2 N1 99.62(19) C3 C2 C33 113.88(19) C34 C2 N1 111.94(16) C34 C2 C3 113.1(2) C34 C2 C33 109.06(19) C2 C3 C4 106.9(2) C1 C4 C3 103.41(16) C1 C4 C5 112.87(16) C1 C4 C20 108.61(15) C3 C4 C20 111.24(16) C5 C4 C3 112.26(18) C5 C4 C20 108.39(16) C6 C5 C4 114.33(18) C5 C6 C7 114.58(17) C6 C7 C8 109.60(16) C6 C7 C19 107.56(15) C19 C7 C8 106.42(17) C35 C7 C6 109.46(17) C35 C7 C8 111.68(17) C35 C7 C19 111.99(16) C9 C8 C7 114.49(17) C9 C8 C16 109.82(16) C16 C8 C7 113.38(16) C10 C9 C8 112.31(18) C11 C10 C9 112.21(17) C10 C11 C12 116.61(17) C10 C11 C15 107.19(16) C10 C11 C36 110.51(17) C15 C11 C12 99.17(17) C36 C11 C12 110.62(17) C36 C11 C15 112.23(16) C11 C12 C13 103.58(17) C37 C12 C11 120.47(18) C37 C12 C13 111.95(19) C14 C13 C12 106.95(19) C15 C14 C13 103.17(16) C14 C15 C11 104.11(17) C14 C15 C16 119.57(17) C16 C15 C11 115.27(18) C15 C16 C8 107.78(16) C15 C16 C17 110.52(18) C17 C16 C8 111.61(16) C18 C17 C16 113.06(18) C19 C18 C17 110.24(17) C18 C19 C7 112.10(16) C18 C19 C20 111.76(16) C20 C19 C7 112.96(17) C19 C20 C4 113.52(15) C22 C21 N1 118.98(18) C22 C21 C26 121.99(18) C26 C21 N1 119.04(18) C21 C22 C27 123.76(18) C23 C22 C21 117.26(19) C23 C22 C27 118.84(19) C24 C23 C22 121.5(2) C25 C24 C23 120.0(2) C24 C25 C26 121.0(2) C21 C26 C30 122.21(18) C25 C26 C21 117.72(19) C25 C26 C30 119.77(18) C22 C27 C28 113.04(19) C22 C27 C29 109.99(18) C28 C27 C29 110.2(2) C26 C30 C31 108.46(19) C26 C30 C32 114.06(19) C32 C30 C31 110.33(18) C12 C37 C38 108.42(18) C44 C37 C12 113.36(19) C44 C37 C38 110.47(18) C39 C38 C37 116.3(2) C38 C39 C40 112.0(3) C41 C40 C39 115.45(19) C40 C41 C42 110.6(2) C40 C41 C43 111.2(2) C42 C41 C43 109.3(2) N1A C1A C2A 179.4(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cu1 Cl1 2.1071(5) Cu1 C1 1.8809(17) N1 C1 1.306(3) N1 C2 1.535(3) N1 C21 1.454(2) C1 C4 1.519(3) C2 C3 1.529(3) C2 C33 1.538(3) C2 C34 1.511(3) C3 C4 1.546(3) C4 C5 1.540(3) C4 C20 1.554(3) C5 C6 1.527(3) C6 C7 1.546(3) C7 C8 1.549(3) C7 C19 1.548(3) C7 C35 1.543(3) C8 C9 1.542(3) C8 C16 1.544(3) C9 C10 1.535(3) C10 C11 1.532(3) C11 C12 1.552(3) C11 C15 1.551(3) C11 C36 1.536(3) C12 C13 1.556(3) C12 C37 1.541(3) C13 C14 1.546(3) C14 C15 1.525(3) C15 C16 1.525(3) C16 C17 1.534(3) C17 C18 1.527(3) C18 C19 1.524(3) C19 C20 1.527(3) C21 C22 1.405(3) C21 C26 1.406(3) C22 C23 1.397(3) C22 C27 1.524(3) C23 C24 1.383(3) C24 C25 1.382(3) C25 C26 1.397(3) C26 C30 1.523(3) C27 C28 1.532(3) C27 C29 1.533(3) C30 C31 1.541(3) C30 C32 1.525(3) C37 C38 1.545(3) C37 C44 1.529(3) C38 C39 1.528(4) C39 C40 1.534(4) C40 C41 1.527(4) C41 C42 1.529(4) C41 C43 1.532(4) N1A C1A 1.115(4) C1A C2A 1.444(5)