#------------------------------------------------------------------------------ #$Date: 2025-05-03 02:47:55 +0100 (Sat, 03 May 2025) $ #$Revision: 299503 $ #$URL: svn://www.crystallography.net/cod/cif/2/02/34/2023489.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2023489 loop_ _publ_author_name 'Tsymbal, Liudmyla V.' 'Andriichuk, Irina L.' 'Stoica, Alexandru-Constantin' 'Lampeka, Yaroslaw D.' _publ_section_title ; Synthesis and structural characterization of the dichloride complex formed by carboxy-functionalized Cu(diazacyclam)2+ cation and its heterometallic coordination polymer with CdCl2 ; _journal_coeditor_code HB8137 _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E Crystallographic Communications' _journal_paper_doi 10.1107/S2056989025003792 _journal_volume 81 _journal_year 2025 _chemical_formula_iupac '[Cu Cl2 (C16 H34 N6 O4)]' _chemical_formula_moiety 'C16 H34 Cl2 Cu N6 O4' _chemical_formula_sum 'C16 H34 Cl2 Cu N6 O4' _chemical_formula_weight 508.93 _chemical_name_systematic '[3,10-Bis(3-carboxypropyl)-1,3,5,8,10,12-hexaazacyclotetradecane-\k^4^N^1^,N^5^,N^8^,N^12^]dichloridocopper(II)' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_method ; Olex2 1.5 (compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928) ; _cell_angle_alpha 90 _cell_angle_beta 99.808(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.0036(5) _cell_length_b 15.8231(7) _cell_length_c 6.9325(3) _cell_measurement_reflns_used 1452 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 24.89 _cell_measurement_theta_min 2.02 _cell_volume 1081.29(9) _computing_cell_refinement ; CrysAlisPro (Rigaku OD, 2022) ; _computing_data_collection ; CrysAlisPro (Rigaku OD, 2022) ; _computing_data_reduction ; CrysAlisPro (Rigaku OD, 2022) ; _computing_molecular_graphics ; Mercury (Macrae et al., 2020) ; _computing_publication_material ; publCIF (Westrip, 2010) ; _computing_structure_refinement ; SHELXL2018/3 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT2018/2 (Sheldrick, 2015a) ; _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0891 _diffrn_reflns_av_unetI/netI 0.0359 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 5849 _diffrn_reflns_theta_full 24.805 _diffrn_reflns_theta_max 24.805 _diffrn_reflns_theta_min 2.066 _exptl_absorpt_coefficient_mu 1.293 _exptl_absorpt_correction_T_max 0.920 _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku OD, 2022) ; _exptl_crystal_colour 'clear light violet' _exptl_crystal_density_diffrn 1.563 _exptl_crystal_description prism _exptl_crystal_F_000 534 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.298 _refine_diff_density_min -0.330 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 1844 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0292 _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^)+(0.0246P)^2^+0.8397P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.0667 _reflns_number_gt 1509 _reflns_number_total 1844 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file hb8137.cif _cod_data_source_block I _cod_database_code 2023489 _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_min 0.860 _shelx_estimated_absorpt_t_max 0.926 _shelx_hkl_file ; -1 0 0 -464 464 -2 1 0 0 -464 464 1 -2 0 0 101276 1928 -2 2 0 0 101276 1928 1 -3 0 0 1867810 19105 -2 3 0 0 1867810 19105 1 -4 0 0 1256039 26148 -2 4 0 0 1256039 26148 1 -5 0 0 528956 13015 -2 5 0 0 528956 13015 1 -6 0 0 283319 5133 -2 6 0 0 283319 5133 1 -7 0 0 528624 7926 -2 7 0 0 528624 7926 1 -8 0 0 585190 11332 -2 8 0 0 585190 11332 1 -9 0 0 125774 4442 -2 9 0 0 125774 4442 1 -10 0 0 263562 12383 -2 10 0 0 263562 12383 1 -11 0 0 40716 4551 -2 11 0 0 40716 4551 1 -1 -1 0 173 229 -2 1 1 0 173 229 1 -2 -1 0 22 586 -2 2 1 0 22 586 1 -3 -1 0 47912 1281 -2 3 1 0 47912 1281 1 -4 -1 0 727 938 -2 4 1 0 727 938 1 -5 -1 0 -1089 1089 -2 5 1 0 -1089 1089 1 -6 -1 0 76769 2128 -2 6 1 0 76769 2128 1 -7 -1 0 1227 1447 -2 7 1 0 1227 1447 1 -8 -1 0 108028 4275 -2 8 1 0 108028 4275 1 -9 -1 0 2507 1824 -2 9 1 0 2507 1824 1 -10 -1 0 16244 2654 -2 10 1 0 16244 2654 1 -11 -1 0 27190 2982 -2 11 1 0 27190 2982 1 0 -2 0 583061 5153 -2 0 2 0 583061 5153 1 -1 -2 0 1175158 6731 -2 1 2 0 1175158 6731 1 -2 -2 0 39311 966 -2 2 2 0 39311 966 1 -3 -2 0 462342 3871 -2 3 2 0 462342 3871 1 -4 -2 0 677470 8514 -2 4 2 0 677470 8514 1 -5 -2 0 920993 8752 -2 5 2 0 920993 8752 1 -6 -2 0 122411 2523 -2 6 2 0 122411 2523 1 -7 -2 0 76877 3313 -2 7 2 0 76877 3313 1 -8 -2 0 71210 3251 -2 8 2 0 71210 3251 1 -9 -2 0 102573 5257 -2 9 2 0 102573 5257 1 -10 -2 0 68753 4008 -2 10 2 0 68753 4008 1 -11 -2 0 29381 3239 -2 11 2 0 29381 3239 1 -1 -3 0 17726 701 -2 1 3 0 17726 701 1 -2 -3 0 60095 1302 -2 2 3 0 60095 1302 1 -3 -3 0 439140 3786 -2 3 3 0 439140 3786 1 -4 -3 0 131659 3309 -2 4 3 0 131659 3309 1 -5 -3 0 839 1136 -2 5 3 0 839 1136 1 -6 -3 0 191273 3201 -2 6 3 0 191273 3201 1 -7 -3 0 11179 1624 -2 7 3 0 11179 1624 1 -8 -3 0 -623 1633 -2 8 3 0 -623 1633 1 -9 -3 0 44642 2636 -2 9 3 0 44642 2636 1 -10 -3 0 43434 3102 -2 10 3 0 43434 3102 1 -11 -3 0 22494 2942 -2 11 3 0 22494 2942 1 0 -4 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596 1 0 2 1 38618 625 1 1 2 1 87105 1314 1 2 2 1 458308 3536 1 3 2 1 119139 1954 1 4 2 1 50735 1587 1 5 2 1 45433 2061 1 6 2 1 1824 1361 1 7 2 1 258 1547 1 8 2 1 135893 3208 1 9 2 1 22188 2207 1 10 2 1 3459 2289 1 11 2 1 8726 3089 1 -11 3 1 14972 2712 1 -10 3 1 60033 3152 1 -9 3 1 2084 2163 1 -8 3 1 3024 1781 1 -7 3 1 95520 2423 1 -6 3 1 126250 2445 1 -5 3 1 110274 2164 1 -4 3 1 363148 3390 1 -3 3 1 473380 4121 1 -2 3 1 92691 1574 1 -1 3 1 48001 865 1 0 3 1 2005376 14852 1 1 3 1 85022 1352 1 2 3 1 39659 1163 1 3 3 1 676206 8128 1 4 3 1 441905 4401 1 5 3 1 500389 6243 1 6 3 1 256781 3624 1 7 3 1 31438 1941 1 8 3 1 80597 2885 1 9 3 1 63247 3575 1 10 3 1 132027 4501 1 11 3 1 77503 4414 1 -11 4 1 -2440 2440 1 -10 4 1 -2217 2217 1 -9 4 1 45492 2775 1 -8 4 1 -112 1768 1 -7 4 1 28353 1941 1 -6 4 1 5209 1456 1 -5 4 1 2805 1029 1 -4 4 1 28379 1157 1 -3 4 1 9592 838 1 -2 4 1 66892 1663 1 -1 4 1 1677 681 1 0 4 1 -430 661 1 1 4 1 209526 2095 1 2 4 1 120766 1820 1 3 4 1 139631 2757 1 4 4 1 39070 1476 1 5 4 1 -258 1222 1 6 4 1 240 1409 1 7 4 1 -1042 1580 1 8 4 1 5705 1896 1 9 4 1 29346 2344 1 10 4 1 1327 2525 1 -11 5 1 -770 2513 1 -10 5 1 36561 2932 1 -9 5 1 22864 2767 1 -8 5 1 10274 1973 1 -7 5 1 24296 1902 1 -6 5 1 44223 1741 1 -5 5 1 218884 2578 1 -4 5 1 3040 927 1 -3 5 1 82287 3288 1 -2 5 1 779504 6220 1 -1 5 1 432303 3436 1 0 5 1 108435 2389 1 1 5 1 1195912 8187 1 2 5 1 197823 2166 1 3 5 1 271588 3166 1 4 5 1 239184 3117 1 5 5 1 727185 6681 1 6 5 1 357452 4697 1 7 5 1 131704 3755 1 8 5 1 220005 5918 1 9 5 1 196113 6506 1 10 5 1 139955 4415 1 -11 6 1 -2309 2559 1 -10 6 1 19157 2705 1 -9 6 1 23638 2519 1 -8 6 1 3025 1894 1 -7 6 1 6013 1448 1 -6 6 1 134774 2371 1 -5 6 1 214206 3078 1 -4 6 1 47229 1578 1 -3 6 1 119352 2194 1 -2 6 1 183210 2904 1 -1 6 1 991 866 1 0 6 1 43323 1187 1 1 6 1 66 830 1 2 6 1 79938 1415 1 3 6 1 9476 1253 1 4 6 1 48239 2356 1 5 6 1 7344 1393 1 6 6 1 27251 2100 1 7 6 1 5454 1769 1 8 6 1 6911 1912 1 9 6 1 25855 3316 1 10 6 1 1258 2573 1 -10 7 1 59475 3579 1 -9 7 1 54888 2796 1 -8 7 1 22734 2198 1 -7 7 1 34723 2232 1 -6 7 1 210053 3396 1 -5 7 1 81402 2334 1 -4 7 1 74515 1927 1 -3 7 1 1416 1106 1 -2 7 1 177063 3565 1 -1 7 1 294255 2904 1 0 7 1 348297 3065 1 1 7 1 122354 1862 1 2 7 1 134083 1792 1 3 7 1 61805 1993 1 4 7 1 198760 3032 1 5 7 1 10242 1509 1 6 7 1 69750 2203 1 7 7 1 125858 3127 1 8 7 1 49080 3712 1 9 7 1 46120 3782 1 10 7 1 38967 3201 1 -10 8 1 7365 2594 1 -9 8 1 16738 2550 1 -8 8 1 36630 2465 1 -7 8 1 27560 2016 1 -6 8 1 37618 2163 1 -5 8 1 5853 1661 1 -4 8 1 674 1262 1 -3 8 1 283 1169 1 -2 8 1 82044 1890 1 -1 8 1 67537 1774 1 0 8 1 24754 1149 1 1 8 1 19093 1147 1 2 8 1 9037 995 1 3 8 1 355 1213 1 4 8 1 31036 1700 1 5 8 1 2367 1493 1 6 8 1 32252 1916 1 7 8 1 -1272 1728 1 8 8 1 1398 2326 1 9 8 1 2952 2514 1 10 8 1 3386 2942 1 -10 9 1 64132 4366 1 -9 9 1 113787 4131 1 -8 9 1 75529 2947 1 -7 9 1 39195 2225 1 -6 9 1 202906 4112 1 -5 9 1 343017 6859 1 -4 9 1 52862 2109 1 -3 9 1 88508 2113 1 -2 9 1 6904 1251 1 -1 9 1 150212 2403 1 0 9 1 60356 1676 1 1 9 1 -448 1082 1 2 9 1 43173 1383 1 3 9 1 65136 1894 1 4 9 1 2518 1454 1 5 9 1 25055 1862 1 6 9 1 -1667 1667 1 7 9 1 1155 1985 1 8 9 1 -1094 2359 1 9 9 1 -1836 2614 1 -9 10 1 16022 2676 1 -8 10 1 -1994 1994 1 -7 10 1 3224 1868 1 -6 10 1 48898 2456 1 -5 10 1 7333 1815 1 -4 10 1 13268 1824 1 -3 10 1 12304 1570 1 -2 10 1 7553 1373 1 -1 10 1 -869 1260 1 0 10 1 22871 1446 1 1 10 1 57058 2334 1 2 10 1 24774 1393 1 3 10 1 9724 1413 1 4 10 1 -873 1424 1 5 10 1 11470 2024 1 6 10 1 5016 2238 1 7 10 1 -1993 2094 1 8 10 1 3016 2549 1 9 10 1 -2241 2671 1 -9 11 1 52121 5692 1 -8 11 1 67616 4495 1 -7 11 1 20369 2467 1 -6 11 1 65498 2745 1 -5 11 1 119250 3098 1 -4 11 1 122175 4043 1 -3 11 1 57927 2300 1 -2 11 1 142885 3013 1 -1 11 1 150083 3051 1 0 11 1 13060 1417 1 1 11 1 79986 2170 1 2 11 1 92620 2026 1 3 11 1 413 1523 1 4 11 1 46088 2119 1 5 11 1 118823 3396 1 6 11 1 37949 2871 1 7 11 1 830 2181 1 8 11 1 -955 2503 1 9 11 1 20487 3790 1 -8 12 1 42053 3236 1 -7 12 1 3894 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2289 1 -2 -1 8 20619 2578 -2 -2 1 8 20619 2578 1 -3 -1 8 58882 3363 -2 -1 1 8 58882 3363 1 -4 -1 8 36188 3108 -2 0 1 8 36188 3108 1 -1 -2 8 6816 2268 -2 -3 2 8 6816 2268 1 -2 -2 8 24455 4083 -2 -2 2 8 24455 4083 1 -3 -2 8 53761 3261 -2 -1 2 8 53761 3261 1 -1 -3 8 21560 2555 -2 -3 3 8 21560 2555 1 -2 -3 8 51877 4204 -2 -2 3 8 51877 4204 1 -3 -3 8 50080 3182 -2 -1 3 8 50080 3182 1 ; _shelx_hkl_checksum 89873 _shelx_res_file ; TITL I_a.res in P2(1)/c I.res created by SHELXL-2018/3 at 10:23:16 on 29-Dec-2024 REM Old TITL I in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.162, Rweak 0.016, Alpha 0.039 REM 0.253 for 83 systematic absences, Orientation as input REM Formula found by SHELXT: C16 N4 O6 Fe2 Cu CELL 0.71073 10.0036 15.8231 6.9325 90 99.808 90 ZERR 2 0.0005 0.0007 0.0003 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl Cu N O UNIT 32 68 4 2 12 8 L.S. 12 0 0 PLAN 1 SIZE 0.06 0.07 0.12 TEMP -173(2) CONF BIND Cu1 Cl1 BOND list 4 MORE -1 BOND $H fmap 2 53 acta OMIT 1 0 0 OMIT 2 0 0 REM REM REM WGHT 0.024600 0.839700 BASF 0.15700 FVAR 10.45541 CU1 4 1.000000 0.500000 0.500000 10.50000 0.01366 0.01469 = 0.01713 -0.00231 0.00270 -0.00050 CL1 3 1.019685 0.392659 0.840766 11.00000 0.02129 0.02181 = 0.01606 0.00172 0.00339 -0.00019 N3 5 0.990417 0.400640 0.319073 11.00000 0.01402 0.01705 = 0.01548 0.00235 -0.00021 -0.00084 AFIX 13 H3 2 0.975658 0.422479 0.181720 11.00000 -1.20000 AFIX 0 O1 6 0.289960 0.309892 -0.005455 11.00000 0.02092 0.03005 = 0.03322 0.00702 0.00562 -0.00029 AFIX 148 H1C 2 0.212867 0.338098 -0.067525 11.00000 -1.50000 AFIX 0 O2 6 0.392820 0.392946 -0.194209 11.00000 0.02333 0.03297 = 0.03431 0.01559 0.00065 0.00100 N1 5 0.798504 0.512656 0.468837 11.00000 0.01795 0.01660 = 0.01215 0.00093 0.00340 0.00035 AFIX 13 H1 2 0.768622 0.542496 0.341645 11.00000 -1.20000 AFIX 0 N2 5 0.746483 0.376646 0.305373 11.00000 0.01757 0.01878 = 0.01524 0.00050 -0.00097 -0.00185 C1 1 0.721172 0.432395 0.458534 11.00000 0.01779 0.02185 = 0.01880 0.00161 0.00391 -0.00266 AFIX 23 H1A 2 0.744468 0.402711 0.585529 11.00000 -1.20000 H1B 2 0.623066 0.445666 0.438437 11.00000 -1.20000 AFIX 0 C8 1 0.396947 0.337404 -0.074674 11.00000 0.02337 0.01841 = 0.01638 -0.00415 0.00321 -0.00368 C5 1 0.697616 0.406427 0.104507 11.00000 0.01574 0.02312 = 0.01851 0.00400 -0.00045 -0.00313 AFIX 23 H5A 2 0.771170 0.437569 0.056237 11.00000 -1.20000 H5B 2 0.620731 0.445800 0.104723 11.00000 -1.20000 AFIX 0 C4 1 0.770015 0.570186 0.624281 11.00000 0.01459 0.02296 = 0.01773 -0.00214 0.00363 0.00510 AFIX 23 H4A 2 0.776660 0.539459 0.749953 11.00000 -1.20000 H4B 2 0.677474 0.593952 0.589865 11.00000 -1.20000 AFIX 0 C7 1 0.524522 0.291653 0.014201 11.00000 0.02223 0.02066 = 0.01907 -0.00004 -0.00062 -0.00119 AFIX 23 H7A 2 0.519929 0.232826 -0.035123 11.00000 -1.20000 H7B 2 0.529656 0.289377 0.157987 11.00000 -1.20000 AFIX 0 C3 1 1.125341 0.359950 0.358484 11.00000 0.02052 0.01829 = 0.01329 -0.00176 0.00213 0.00694 AFIX 23 H3A 2 1.136479 0.321178 0.250265 11.00000 -1.20000 H3B 2 1.135718 0.327019 0.481560 11.00000 -1.20000 AFIX 0 C6 1 0.652212 0.332957 -0.031382 11.00000 0.02129 0.02975 = 0.01651 -0.00186 0.00193 0.00318 AFIX 23 H6A 2 0.635330 0.353432 -0.168322 11.00000 -1.20000 H6B 2 0.725710 0.290396 -0.019189 11.00000 -1.20000 AFIX 0 C2 1 0.879892 0.339477 0.336013 11.00000 0.02024 0.01539 = 0.01619 0.00152 0.00042 -0.00235 AFIX 23 H2A 2 0.881701 0.293733 0.239062 11.00000 -1.20000 H2B 2 0.897761 0.313604 0.467921 11.00000 -1.20000 AFIX 0 HKLF 5 REM I_a.res in P2(1)/c REM wR2 = 0.0667, GooF = S = 1.054, Restrained GooF = 1.054 for all data REM R1 = 0.0292 for 1509 Fo > 4sig(Fo) and 0.0447 for all 1844 data REM 136 parameters refined using 0 restraints END WGHT 0.0247 0.8434 REM Highest difference peak 0.298, deepest hole -0.330, 1-sigma level 0.068 Q1 1 0.8797 0.4829 0.4807 11.00000 0.05 0.30 ; _shelx_res_checksum 59132 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu1 1.000000 0.500000 0.500000 0.01515(14) Uani d 1 . . Cl Cl1 1.01968(7) 0.39266(4) 0.84077(10) 0.01969(18) Uani d 1 . . N N3 0.9904(2) 0.40064(14) 0.3191(3) 0.0158(5) Uani d 1 . . H H3 0.975658 0.422479 0.181720 0.019 Uiso calc 1 . . O O1 0.2900(2) 0.30989(14) -0.0055(3) 0.0279(5) Uani d 1 . . H H1C 0.213(3) 0.338(2) -0.068(4) 0.042 Uiso calc 1 . . O O2 0.3928(2) 0.39295(14) -0.1942(3) 0.0307(6) Uani d 1 . . N N1 0.7985(2) 0.51266(14) 0.4688(3) 0.0155(5) Uani d 1 . . H H1 0.768622 0.542496 0.341645 0.019 Uiso calc 1 . . N N2 0.7465(2) 0.37665(15) 0.3054(3) 0.0176(5) Uani d 1 . . C C1 0.7212(3) 0.43239(18) 0.4585(4) 0.0194(7) Uani d 1 . . H H1A 0.744468 0.402711 0.585529 0.023 Uiso calc 1 . . H H1B 0.623066 0.445666 0.438437 0.023 Uiso calc 1 . . C C8 0.3969(3) 0.33740(19) -0.0747(4) 0.0194(7) Uani d 1 . . C C5 0.6976(3) 0.40643(19) 0.1045(4) 0.0195(7) Uani d 1 . . H H5A 0.771170 0.437569 0.056237 0.023 Uiso calc 1 . . H H5B 0.620731 0.445800 0.104723 0.023 Uiso calc 1 . . C C4 0.7700(3) 0.57019(18) 0.6243(4) 0.0183(6) Uani d 1 . . H H4A 0.776660 0.539459 0.749953 0.022 Uiso calc 1 . . H H4B 0.677474 0.593952 0.589865 0.022 Uiso calc 1 . . C C7 0.5245(3) 0.29165(19) 0.0142(4) 0.0211(7) Uani d 1 . . H H7A 0.519929 0.232826 -0.035123 0.025 Uiso calc 1 . . H H7B 0.529656 0.289377 0.157987 0.025 Uiso calc 1 . . C C3 1.1253(3) 0.35995(18) 0.3585(4) 0.0175(6) Uani d 1 . . H H3A 1.136479 0.321178 0.250265 0.021 Uiso calc 1 . . H H3B 1.135718 0.327019 0.481560 0.021 Uiso calc 1 . . C C6 0.6522(3) 0.3330(2) -0.0314(4) 0.0227(7) Uani d 1 . . H H6A 0.635330 0.353432 -0.168322 0.027 Uiso calc 1 . . H H6B 0.725710 0.290396 -0.019189 0.027 Uiso calc 1 . . C C2 0.8799(3) 0.33948(18) 0.3360(4) 0.0176(6) Uani d 1 . . H H2A 0.881701 0.293733 0.239062 0.021 Uiso calc 1 . . H H2B 0.897761 0.313604 0.467921 0.021 Uiso calc 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.0137(2) 0.0147(2) 0.0171(3) -0.0005(2) 0.0027(2) -0.0023(2) Cl1 0.0213(4) 0.0218(4) 0.0161(4) -0.0002(3) 0.0034(3) 0.0017(3) N3 0.0140(12) 0.0170(12) 0.0155(12) -0.0008(10) -0.0002(10) 0.0024(9) O1 0.0209(12) 0.0300(13) 0.0332(12) -0.0003(10) 0.0056(10) 0.0070(10) O2 0.0233(12) 0.0330(13) 0.0343(13) 0.0010(10) 0.0007(10) 0.0156(11) N1 0.0180(12) 0.0166(14) 0.0122(12) 0.0004(10) 0.0034(10) 0.0009(10) N2 0.0176(13) 0.0188(13) 0.0152(13) -0.0019(11) -0.0010(10) 0.0005(10) C1 0.0178(16) 0.0219(16) 0.0188(16) -0.0027(13) 0.0039(12) 0.0016(13) C8 0.0234(17) 0.0184(16) 0.0164(15) -0.0037(13) 0.0032(13) -0.0041(13) C5 0.0157(15) 0.0231(17) 0.0185(15) -0.0031(13) -0.0005(12) 0.0040(12) C4 0.0146(15) 0.0230(16) 0.0177(16) 0.0051(13) 0.0036(12) -0.0021(13) C7 0.0222(18) 0.0207(16) 0.0191(15) -0.0012(13) -0.0006(13) 0.0000(13) C3 0.0205(16) 0.0183(16) 0.0133(14) 0.0069(12) 0.0021(12) -0.0018(12) C6 0.0213(17) 0.0298(18) 0.0165(16) 0.0032(14) 0.0019(13) -0.0019(13) C2 0.0202(16) 0.0154(15) 0.0162(15) -0.0023(13) 0.0004(12) 0.0015(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N3 Cu1 Cl1 3_766 . 87.71(7) ? N3 Cu1 Cl1 . . 92.29(6) ? N3 Cu1 N3 3_766 . 180.0 ? N1 Cu1 Cl1 3_766 . 85.74(7) ? N1 Cu1 Cl1 . . 94.26(7) ? N1 Cu1 N3 3_766 3_766 94.08(9) ? N1 Cu1 N3 . 3_766 85.92(9) y N1 Cu1 N3 3_766 . 85.92(9) ? N1 Cu1 N3 . . 94.08(9) y N1 Cu1 N1 . 3_766 180.0 ? Cu1 N3 H3 . . 108.0 ? C3 N3 Cu1 . . 106.34(16) ? C3 N3 H3 . . 108.0 ? C3 N3 C2 . . 111.7(2) ? C2 N3 Cu1 . . 114.69(17) ? C2 N3 H3 . . 108.0 ? C8 O1 H1C . . 109.5 ? Cu1 N1 H1 . . 106.7 ? C1 N1 Cu1 . . 115.30(18) ? C1 N1 H1 . . 106.7 ? C4 N1 Cu1 . . 107.42(17) ? C4 N1 H1 . . 106.7 ? C4 N1 C1 . . 113.6(2) ? C1 N2 C5 . . 115.5(2) ? C1 N2 C2 . . 114.7(2) ? C2 N2 C5 . . 114.8(2) ? N1 C1 H1A . . 108.8 ? N1 C1 H1B . . 108.8 ? N2 C1 N1 . . 113.9(2) ? N2 C1 H1A . . 108.8 ? N2 C1 H1B . . 108.8 ? H1A C1 H1B . . 107.7 ? O1 C8 C7 . . 112.1(3) ? O2 C8 O1 . . 123.8(3) ? O2 C8 C7 . . 124.1(3) ? N2 C5 H5A . . 109.4 ? N2 C5 H5B . . 109.4 ? N2 C5 C6 . . 111.0(2) ? H5A C5 H5B . . 108.0 ? C6 C5 H5A . . 109.4 ? C6 C5 H5B . . 109.4 ? N1 C4 H4A . . 110.3 ? N1 C4 H4B . . 110.3 ? N1 C4 C3 . 3_766 106.9(2) ? H4A C4 H4B . . 108.6 ? C3 C4 H4A 3_766 . 110.3 ? C3 C4 H4B 3_766 . 110.3 ? C8 C7 H7A . . 108.9 ? C8 C7 H7B . . 108.9 ? C8 C7 C6 . . 113.2(2) ? H7A C7 H7B . . 107.8 ? C6 C7 H7A . . 108.9 ? C6 C7 H7B . . 108.9 ? N3 C3 C4 . 3_766 107.1(2) ? N3 C3 H3A . . 110.3 ? N3 C3 H3B . . 110.3 ? C4 C3 H3A 3_766 . 110.3 ? C4 C3 H3B 3_766 . 110.3 ? H3A C3 H3B . . 108.6 ? C5 C6 H6A . . 109.2 ? C5 C6 H6B . . 109.2 ? C7 C6 C5 . . 112.0(2) ? C7 C6 H6A . . 109.2 ? C7 C6 H6B . . 109.2 ? H6A C6 H6B . . 107.9 ? N3 C2 H2A . . 108.8 ? N3 C2 H2B . . 108.8 ? N2 C2 N3 . . 113.9(2) ? N2 C2 H2A . . 108.8 ? N2 C2 H2B . . 108.8 ? H2A C2 H2B . . 107.7 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cu1 Cl1 . 2.8889(7) y Cu1 N3 . 2.003(2) y Cu1 N3 3_766 2.003(2) ? Cu1 N1 3_766 2.000(2) ? Cu1 N1 . 2.000(2) y N3 H3 . 1.0000 ? N3 C3 . 1.478(4) ? N3 C2 . 1.489(4) ? O1 H1C . 0.93(4) ? O1 C8 . 1.319(4) ? O2 C8 . 1.204(3) ? N1 H1 . 1.0000 ? N1 C1 . 1.482(4) ? N1 C4 . 1.475(4) ? N2 C1 . 1.436(4) ? N2 C5 . 1.472(4) ? N2 C2 . 1.441(4) ? C1 H1A . 0.9900 ? C1 H1B . 0.9900 ? C8 C7 . 1.505(4) ? C5 H5A . 0.9900 ? C5 H5B . 0.9900 ? C5 C6 . 1.516(4) ? C4 H4A . 0.9900 ? C4 H4B . 0.9900 ? C4 C3 3_766 1.513(4) ? C7 H7A . 0.9900 ? C7 H7B . 0.9900 ? C7 C6 . 1.515(4) ? C3 H3A . 0.9900 ? C3 H3B . 0.9900 ? C6 H6A . 0.9900 ? C6 H6B . 0.9900 ? C2 H2A . 0.9900 ? C2 H2B . 0.9900 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O2 3_665 1.00 2.03 2.877(3) 141.0 yes O1 H1C Cl1 1_454 0.93(3) 2.12(3) 3.030(2) 168(3) yes N3 H3 Cl1 1_554 1.00 2.52 3.381(2) 144.2 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Cu1 N3 C3 C4 . . . 3_766 -43.6(2) ? Cu1 N3 C2 N2 . . . . 57.0(3) ? Cu1 N1 C1 N2 . . . . -56.5(3) ? Cu1 N1 C4 C3 . . . 3_766 40.6(2) ? O1 C8 C7 C6 . . . . -168.6(2) ? O2 C8 C7 C6 . . . . 11.0(4) ? N2 C5 C6 C7 . . . . 68.7(3) ? C1 N1 C4 C3 . . . 3_766 169.3(2) ? C1 N2 C5 C6 . . . . -146.7(3) ? C1 N2 C2 N3 . . . . -70.1(3) ? C8 C7 C6 C5 . . . . 82.0(3) ? C5 N2 C1 N1 . . . . -67.4(3) ? C5 N2 C2 N3 . . . . 67.2(3) ? C4 N1 C1 N2 . . . . 179.0(2) ? C3 N3 C2 N2 . . . . 178.0(2) ? C2 N3 C3 C4 . . . 3_766 -169.4(2) ? C2 N2 C1 N1 . . . . 69.6(3) ? C2 N2 C5 C6 . . . . 76.4(3) ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.8430(16) 2 0.1570(16)