#------------------------------------------------------------------------------ #$Date: 2018-01-16 07:23:00 +0200 (Tue, 16 Jan 2018) $ #$Revision: 205243 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229988.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_7229988 loop_ _publ_author_name 'Li, Jie' 'Liu, Huiyu' 'Guo, Zhaoqi' 'Yang, Mingyan' 'Song, Jirong' 'Ma, Haixia' _publ_section_title ; Two Cu(ii)-triadimenol complexes as potential fungicides: synergistic actions and DFT calculations ; _journal_issue 6 _journal_name_full 'RSC Advances' _journal_page_first 2933 _journal_paper_doi 10.1039/C7RA10572J _journal_volume 8 _journal_year 2018 _chemical_formula_sum 'C32 H42 Cl2 Cu N6 O8' _chemical_formula_weight 773.15 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2015-11-07 deposited with the CCDC. 2018-01-08 downloaded from the CCDC. ; _cell_angle_alpha 111.668(4) _cell_angle_beta 108.999(4) _cell_angle_gamma 96.088(3) _cell_formula_units_Z 1 _cell_length_a 8.5849(16) _cell_length_b 10.5243(19) _cell_length_c 12.043(3) _cell_measurement_reflns_used 2530 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.13 _cell_measurement_theta_min 2.21 _cell_volume 923.9(3) _computing_cell_refinement ' SAINT (Bruker, 2008)' _computing_data_collection 'APEX2 (Bruker, 2008)' _computing_data_reduction 'SAINT (Bruker, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg, 1999)' _computing_publication_material 'publCIF (Westrip, 2010)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014 (Sheldrick, 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.984 _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 0.0184 _diffrn_reflns_av_unetI/netI 0.0392 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4768 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.499 _diffrn_reflns_theta_min 2.155 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.791 _exptl_absorpt_correction_T_max 0.9733 _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 403 _exptl_crystal_size_max 0.367 _exptl_crystal_size_mid 0.301 _exptl_crystal_size_min 0.243 _refine_diff_density_max 0.461 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 224 _refine_ls_number_reflns 3399 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.140 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0387 _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^)+(0.0741P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1177 _refine_ls_wR_factor_ref 0.1220 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3022 _reflns_number_total 3399 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra10572j2.cif _cod_data_source_block 2 _cod_database_code 7229988 _shelx_shelxl_version_number 2014/7 _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 0.760 _shelx_estimated_absorpt_t_max 0.831 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL xb7899 in P-1 P-1 CELL 0.71073 8.5849 10.5243 12.0430 111.668 108.999 96.088 ZERR 1 0.0016 0.0019 0.0030 0.004 0.004 0.003 LATT 1 SFAC C H Cl Cu N O UNIT 32 42 2 1 6 8 L.S. 20 ACTA omit -3.0 51 BOND $h FMAP 2 PLAN 20 HTAB CONF SIZE 0.367 0.301 0.243 TEMP 23.000 WGHT 0.074100 FVAR 0.21266 MOLE 1 CU1 4 1.500000 0.500000 1.000000 10.50000 0.03352 0.02801 = 0.03548 0.01170 0.01381 0.00450 CL1 3 1.314755 -0.509583 0.548047 11.00000 0.09032 0.05286 = 0.08191 0.03140 0.05688 0.03920 N1 5 1.317361 0.327474 0.862719 11.00000 0.03945 0.03226 = 0.03785 0.01402 0.01666 0.00743 N2 5 1.101782 0.144367 0.764562 11.00000 0.03770 0.02692 = 0.03423 0.01107 0.01104 0.00482 N3 5 1.120813 0.173466 0.668509 11.00000 0.06242 0.03908 = 0.03499 0.01641 0.01047 -0.00332 O1 6 1.251082 0.605748 1.052795 11.00000 0.06984 0.04682 = 0.06940 0.02354 0.03914 0.02576 O2 6 1.415655 0.484102 1.126806 11.00000 0.04579 0.04037 = 0.04099 0.01488 0.01915 0.00489 O3 6 0.906314 0.178984 0.915593 11.00000 0.04569 0.03635 = 0.05183 0.00796 0.01977 0.00948 AFIX 147 H3 2 0.868297 0.248959 0.929154 11.00000 -1.50000 AFIX 0 O4 6 1.028064 -0.056603 0.794737 11.00000 0.04690 0.03038 = 0.03975 0.01493 0.02063 0.01263 C1 1 1.251851 0.284188 0.732621 11.00000 0.05846 0.04087 = 0.03898 0.01848 0.01481 -0.00366 AFIX 43 H1 2 1.296196 0.329330 0.691977 11.00000 -1.20000 AFIX 0 C2 1 1.218980 0.236503 0.878896 11.00000 0.03738 0.03294 = 0.03359 0.01175 0.01300 0.00401 AFIX 43 H2 2 1.230245 0.237018 0.958535 11.00000 -1.20000 AFIX 0 C3 1 0.961026 0.028542 0.734996 11.00000 0.03546 0.02679 = 0.03681 0.01058 0.00972 0.00542 AFIX 13 H3A 2 0.907219 -0.028585 0.640668 11.00000 -1.20000 AFIX 0 C4 1 0.827330 0.085615 0.782706 11.00000 0.03739 0.02987 = 0.04981 0.01129 0.01529 0.00581 AFIX 13 H4 2 0.783771 0.142376 0.736710 11.00000 -1.20000 AFIX 0 C5 1 0.671429 -0.030107 0.750986 11.00000 0.03823 0.04361 = 0.07489 0.01220 0.02362 0.00243 C6 1 0.604373 -0.135405 0.606171 11.00000 0.05232 0.05842 = 0.09356 0.00408 0.01905 -0.01046 AFIX 33 H6A 2 0.690670 -0.181707 0.590505 11.00000 -1.50000 H6B 2 0.504331 -0.204755 0.584891 11.00000 -1.50000 H6C 2 0.576433 -0.085210 0.553093 11.00000 -1.50000 AFIX 0 C7 1 0.713354 -0.108226 0.838242 11.00000 0.07420 0.07171 = 0.11292 0.04307 0.04978 0.00323 AFIX 33 H7A 2 0.799974 -0.155181 0.824621 11.00000 -1.50000 H7B 2 0.753696 -0.041414 0.927733 11.00000 -1.50000 H7C 2 0.612567 -0.176856 0.816849 11.00000 -1.50000 AFIX 0 C8 1 0.534526 0.042620 0.775030 11.00000 0.04357 0.06905 = 0.12734 0.01171 0.03699 0.00886 AFIX 33 H8A 2 0.506241 0.092212 0.721433 11.00000 -1.50000 H8B 2 0.434772 -0.026877 0.753996 11.00000 -1.50000 H8C 2 0.575901 0.108564 0.864881 11.00000 -1.50000 AFIX 0 C9 1 1.092389 -0.161604 0.729396 11.00000 0.03247 0.02533 = 0.03857 0.01032 0.01545 0.00458 C10 1 1.088657 -0.193651 0.607166 11.00000 0.04557 0.04310 = 0.03793 0.01975 0.01560 0.01473 AFIX 43 H10 2 1.043027 -0.141852 0.562481 11.00000 -1.20000 AFIX 0 C11 1 1.153754 -0.304294 0.550841 11.00000 0.04963 0.04541 = 0.03707 0.01262 0.02137 0.01186 AFIX 43 H11 2 1.148466 -0.328918 0.466919 11.00000 -1.20000 AFIX 0 C12 1 1.225694 -0.377074 0.618904 11.00000 0.04730 0.03240 = 0.05394 0.01617 0.02737 0.01300 C13 1 1.231015 -0.344029 0.741921 11.00000 0.07475 0.04777 = 0.05689 0.03092 0.03092 0.03127 AFIX 43 H13 2 1.280368 -0.393777 0.787646 11.00000 -1.20000 AFIX 0 C14 1 1.162992 -0.237086 0.796892 11.00000 0.06886 0.04333 = 0.04252 0.02294 0.02770 0.02317 AFIX 43 H14 2 1.164358 -0.215378 0.879447 11.00000 -1.20000 AFIX 0 C15 1 1.293380 0.544679 1.123526 11.00000 0.05019 0.03620 = 0.04617 0.00674 0.02690 0.00214 C16 1 1.203531 0.536110 1.208753 11.00000 0.09496 0.08405 = 0.09148 0.03478 0.06942 0.02363 AFIX 33 H16A 2 1.254395 0.484837 1.256069 11.00000 -1.50000 H16B 2 1.212978 0.629881 1.268841 11.00000 -1.50000 H16C 2 1.085402 0.488098 1.156191 11.00000 -1.50000 AFIX 0 HKLF 4 1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 REM xb7899 in P-1 P-1 REM R1 = 0.0387 for 3022 Fo > 4sig(Fo) and 0.0436 for all 3399 data REM 224 parameters refined using 0 restraints END WGHT 0.0781 0.1001 REM Instructions for potential hydrogen bonds EQIV $1 -x+2, -y+1, -z+2 HTAB O3 O1_$1 EQIV $2 x, y+1, z HTAB C1 Cl1_$2 EQIV $3 -x+2, -y, -z+1 HTAB C10 N3_$3 EQIV $4 -x+2, -y, -z+2 HTAB C14 O3_$4 REM Highest difference peak 0.461, deepest hole -0.381, 1-sigma level 0.062 Q1 1 1.4890 0.4392 0.9034 11.00000 0.05 0.46 Q2 1 1.3763 0.5042 0.9723 11.00000 0.05 0.34 Q3 1 0.9035 0.0621 0.7628 11.00000 0.05 0.28 Q4 1 1.1756 0.4606 1.1959 11.00000 0.05 0.27 Q5 1 1.1039 0.5666 1.1764 11.00000 0.05 0.26 Q6 1 1.2870 0.5809 1.2802 11.00000 0.05 0.26 Q7 1 1.3408 0.4984 1.1073 11.00000 0.05 0.26 Q8 1 1.1625 0.6170 1.0330 11.00000 0.05 0.25 Q9 1 1.3706 -0.4503 0.6313 11.00000 0.05 0.24 Q10 1 0.7403 -0.1848 0.7819 11.00000 0.05 0.22 Q11 1 1.1253 -0.1716 0.6746 11.00000 0.05 0.22 Q12 1 1.2339 -0.3185 0.6007 11.00000 0.05 0.20 Q13 1 1.1799 -0.1666 0.7757 11.00000 0.05 0.20 Q14 1 1.3710 0.5916 1.3439 11.00000 0.05 0.19 Q15 1 1.2482 -0.2763 0.7825 11.00000 0.05 0.19 Q16 1 1.4570 0.5961 1.2838 11.00000 0.05 0.19 Q17 1 1.3823 -0.3427 0.8283 11.00000 0.05 0.19 Q18 1 0.6400 -0.0787 0.6639 11.00000 0.05 0.18 Q19 1 1.0491 -0.2259 0.6449 11.00000 0.05 0.18 Q20 1 1.2519 -0.4463 0.6007 11.00000 0.05 0.18 ; _shelx_res_checksum 74094 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy Cu1 Cu 1.5000 0.5000 1.0000 0.03320(16) Uani 1 2 d S . P Cl1 Cl 1.31475(11) -0.50958(8) 0.54805(8) 0.0661(2) Uani 1 1 d . . . N1 N 1.3174(2) 0.32747(19) 0.86272(17) 0.0366(4) Uani 1 1 d . . . N2 N 1.1018(2) 0.14437(19) 0.76456(17) 0.0348(4) Uani 1 1 d . . . N3 N 1.1208(3) 0.1735(2) 0.66851(19) 0.0492(5) Uani 1 1 d . . . O1 O 1.2511(3) 0.6057(2) 1.05280(19) 0.0583(5) Uani 1 1 d . . . O2 O 1.4157(2) 0.48410(17) 1.12681(15) 0.0432(4) Uani 1 1 d . . . O3 O 0.9063(2) 0.17898(18) 0.91559(17) 0.0481(4) Uani 1 1 d . . . H3 H 0.8683 0.2490 0.9292 0.072 Uiso 1 1 calc R U . O4 O 1.0281(2) -0.05660(16) 0.79474(15) 0.0378(4) Uani 1 1 d . . . C1 C 1.2519(3) 0.2842(3) 0.7326(2) 0.0483(6) Uani 1 1 d . . . H1 H 1.2962 0.3293 0.6920 0.058 Uiso 1 1 calc R U . C2 C 1.2190(3) 0.2365(2) 0.8789(2) 0.0362(5) Uani 1 1 d . . . H2 H 1.2302 0.2370 0.9585 0.043 Uiso 1 1 calc R U . C3 C 0.9610(3) 0.0285(2) 0.7350(2) 0.0355(5) Uani 1 1 d . . . H3A H 0.9072 -0.0286 0.6407 0.043 Uiso 1 1 calc R U . C4 C 0.8273(3) 0.0856(2) 0.7827(2) 0.0417(6) Uani 1 1 d . . . H4 H 0.7838 0.1424 0.7367 0.050 Uiso 1 1 calc R U . C5 C 0.6714(3) -0.0301(3) 0.7510(3) 0.0568(7) Uani 1 1 d . . . C6 C 0.6044(4) -0.1354(4) 0.6062(4) 0.0821(11) Uani 1 1 d . . . H6A H 0.6907 -0.1817 0.5905 0.123 Uiso 1 1 calc R U . H6B H 0.5043 -0.2048 0.5849 0.123 Uiso 1 1 calc R U . H6C H 0.5764 -0.0852 0.5531 0.123 Uiso 1 1 calc R U . C7 C 0.7134(5) -0.1082(4) 0.8382(4) 0.0829(11) Uani 1 1 d . . . H7A H 0.8000 -0.1552 0.8246 0.124 Uiso 1 1 calc R U . H7B H 0.7537 -0.0414 0.9277 0.124 Uiso 1 1 calc R U . H7C H 0.6126 -0.1769 0.8168 0.124 Uiso 1 1 calc R U . C8 C 0.5345(4) 0.0426(4) 0.7750(4) 0.0893(13) Uani 1 1 d . . . H8A H 0.5062 0.0922 0.7214 0.134 Uiso 1 1 calc R U . H8B H 0.4348 -0.0269 0.7540 0.134 Uiso 1 1 calc R U . H8C H 0.5759 0.1086 0.8649 0.134 Uiso 1 1 calc R U . C9 C 1.0924(3) -0.1616(2) 0.7294(2) 0.0331(5) Uani 1 1 d . . . C10 C 1.0887(3) -0.1937(3) 0.6072(2) 0.0414(5) Uani 1 1 d . . . H10 H 1.0430 -0.1419 0.5625 0.050 Uiso 1 1 calc R U . C11 C 1.1538(3) -0.3043(3) 0.5508(2) 0.0445(6) Uani 1 1 d . . . H11 H 1.1485 -0.3289 0.4669 0.053 Uiso 1 1 calc R U . C12 C 1.2257(3) -0.3771(2) 0.6189(2) 0.0430(6) Uani 1 1 d . . . C13 C 1.2310(4) -0.3440(3) 0.7419(3) 0.0544(7) Uani 1 1 d . . . H13 H 1.2804 -0.3938 0.7876 0.065 Uiso 1 1 calc R U . C14 C 1.1630(4) -0.2371(3) 0.7969(2) 0.0478(6) Uani 1 1 d . . . H14 H 1.1644 -0.2154 0.8794 0.057 Uiso 1 1 calc R U . C15 C 1.2934(3) 0.5447(3) 1.1235(2) 0.0463(6) Uani 1 1 d . . . C16 C 1.2035(5) 0.5361(4) 1.2088(4) 0.0820(11) Uani 1 1 d . . . H16A H 1.2544 0.4848 1.2561 0.123 Uiso 1 1 calc R U . H16B H 1.2130 0.6299 1.2688 0.123 Uiso 1 1 calc R U . H16C H 1.0854 0.4881 1.1562 0.123 Uiso 1 1 calc R U . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0335(2) 0.0280(2) 0.0355(2) 0.01170(17) 0.01381(17) 0.00450(15) Cl1 0.0903(6) 0.0529(4) 0.0819(5) 0.0314(4) 0.0569(4) 0.0392(4) N1 0.0395(10) 0.0323(10) 0.0378(10) 0.0140(8) 0.0167(8) 0.0074(8) N2 0.0377(10) 0.0269(9) 0.0342(9) 0.0111(8) 0.0110(8) 0.0048(8) N3 0.0624(14) 0.0391(11) 0.0350(10) 0.0164(9) 0.0105(10) -0.0033(10) O1 0.0698(13) 0.0468(10) 0.0694(12) 0.0235(10) 0.0391(11) 0.0258(10) O2 0.0458(9) 0.0404(9) 0.0410(9) 0.0149(7) 0.0191(8) 0.0049(7) O3 0.0457(10) 0.0364(9) 0.0518(10) 0.0080(8) 0.0198(8) 0.0095(8) O4 0.0469(9) 0.0304(8) 0.0397(8) 0.0149(7) 0.0206(7) 0.0126(7) C1 0.0585(15) 0.0409(13) 0.0390(12) 0.0185(11) 0.0148(11) -0.0037(11) C2 0.0374(11) 0.0329(11) 0.0336(11) 0.0117(9) 0.0130(9) 0.0040(9) C3 0.0355(11) 0.0268(10) 0.0368(11) 0.0106(9) 0.0097(9) 0.0054(9) C4 0.0374(12) 0.0299(12) 0.0498(13) 0.0113(10) 0.0153(11) 0.0058(10) C5 0.0382(13) 0.0436(15) 0.0749(19) 0.0122(14) 0.0236(13) 0.0024(11) C6 0.0523(18) 0.0584(19) 0.094(2) 0.0041(18) 0.0190(17) -0.0105(15) C7 0.074(2) 0.072(2) 0.113(3) 0.043(2) 0.050(2) 0.0032(18) C8 0.0436(17) 0.069(2) 0.127(3) 0.012(2) 0.0370(19) 0.0089(15) C9 0.0325(11) 0.0253(10) 0.0386(11) 0.0103(9) 0.0154(9) 0.0046(8) C10 0.0456(13) 0.0431(13) 0.0379(12) 0.0198(10) 0.0156(10) 0.0147(11) C11 0.0496(14) 0.0454(14) 0.0371(12) 0.0126(11) 0.0214(11) 0.0119(11) C12 0.0473(13) 0.0324(12) 0.0539(14) 0.0162(11) 0.0274(12) 0.0130(10) C13 0.0748(19) 0.0478(15) 0.0569(15) 0.0309(13) 0.0309(14) 0.0313(14) C14 0.0689(17) 0.0433(14) 0.0425(13) 0.0229(11) 0.0277(12) 0.0232(12) C15 0.0502(14) 0.0362(13) 0.0462(13) 0.0067(11) 0.0269(12) 0.0021(11) C16 0.095(3) 0.084(2) 0.091(2) 0.035(2) 0.069(2) 0.024(2) 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 O2 Cu1 O2 180.00(4) . 2_867 O2 Cu1 N1 90.87(7) . 2_867 O2 Cu1 N1 89.13(7) 2_867 2_867 O2 Cu1 N1 89.13(7) . . O2 Cu1 N1 90.87(7) 2_867 . N1 Cu1 N1 180.00(12) 2_867 . C2 N1 C1 103.24(19) . . C2 N1 Cu1 127.70(16) . . C1 N1 Cu1 128.70(16) . . C2 N2 N3 110.13(19) . . C2 N2 C3 129.13(19) . . N3 N2 C3 120.68(17) . . C1 N3 N2 102.51(18) . . C15 O2 Cu1 108.12(16) . . C4 O3 H3 109.5 . . C9 O4 C3 118.06(17) . . N3 C1 N1 114.4(2) . . N3 C1 H1 122.8 . . N1 C1 H1 122.8 . . N1 C2 N2 109.7(2) . . N1 C2 H2 125.1 . . N2 C2 H2 125.1 . . O4 C3 N2 108.56(17) . . O4 C3 C4 110.21(19) . . N2 C3 C4 111.15(18) . . O4 C3 H3A 109.0 . . N2 C3 H3A 109.0 . . C4 C3 H3A 109.0 . . O3 C4 C3 109.48(18) . . O3 C4 C5 112.9(2) . . C3 C4 C5 114.3(2) . . O3 C4 H4 106.5 . . C3 C4 H4 106.5 . . C5 C4 H4 106.5 . . C8 C5 C7 108.0(3) . . C8 C5 C6 109.2(3) . . C7 C5 C6 110.6(3) . . C8 C5 C4 107.5(2) . . C7 C5 C4 112.4(2) . . C6 C5 C4 109.1(3) . . C5 C6 H6A 109.5 . . C5 C6 H6B 109.5 . . H6A C6 H6B 109.5 . . C5 C6 H6C 109.5 . . H6A C6 H6C 109.5 . . H6B C6 H6C 109.5 . . C5 C7 H7A 109.5 . . C5 C7 H7B 109.5 . . H7A C7 H7B 109.5 . . C5 C7 H7C 109.5 . . H7A C7 H7C 109.5 . . H7B C7 H7C 109.5 . . C5 C8 H8A 109.5 . . C5 C8 H8B 109.5 . . H8A C8 H8B 109.5 . . C5 C8 H8C 109.5 . . H8A C8 H8C 109.5 . . H8B C8 H8C 109.5 . . C10 C9 O4 124.9(2) . . C10 C9 C14 120.4(2) . . O4 C9 C14 114.7(2) . . C9 C10 C11 119.3(2) . . C9 C10 H10 120.3 . . C11 C10 H10 120.3 . . C12 C11 C10 120.0(2) . . C12 C11 H11 120.0 . . C10 C11 H11 120.0 . . C11 C12 C13 120.7(2) . . C11 C12 Cl1 118.65(19) . . C13 C12 Cl1 120.6(2) . . C12 C13 C14 119.6(2) . . C12 C13 H13 120.2 . . C14 C13 H13 120.2 . . C13 C14 C9 120.0(2) . . C13 C14 H14 120.0 . . C9 C14 H14 120.0 . . O1 C15 O2 121.8(2) . . O1 C15 C16 121.7(3) . . O2 C15 C16 116.4(3) . . C15 C16 H16A 109.5 . . C15 C16 H16B 109.5 . . H16A C16 H16B 109.5 . . C15 C16 H16C 109.5 . . H16A C16 H16C 109.5 . . H16B C16 H16C 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cu1 O2 1.9410(16) . Cu1 O2 1.9410(16) 2_867 Cu1 N1 1.9950(18) 2_867 Cu1 N1 1.9950(18) . Cl1 C12 1.741(2) . N1 C2 1.320(3) . N1 C1 1.350(3) . N2 C2 1.324(3) . N2 N3 1.354(3) . N2 C3 1.470(3) . N3 C1 1.308(3) . O1 C15 1.234(3) . O2 C15 1.282(3) . O3 C4 1.406(3) . O3 H3 0.8200 . O4 C9 1.384(3) . O4 C3 1.403(3) . C1 H1 0.9300 . C2 H2 0.9300 . C3 C4 1.526(3) . C3 H3A 0.9800 . C4 C5 1.549(4) . C4 H4 0.9800 . C5 C8 1.516(4) . C5 C7 1.538(5) . C5 C6 1.544(4) . C6 H6A 0.9600 . C6 H6B 0.9600 . C6 H6C 0.9600 . C7 H7A 0.9600 . C7 H7B 0.9600 . C7 H7C 0.9600 . C8 H8A 0.9600 . C8 H8B 0.9600 . C8 H8C 0.9600 . C9 C10 1.372(3) . C9 C14 1.385(3) . C10 C11 1.389(3) . C10 H10 0.9300 . C11 C12 1.369(4) . C11 H11 0.9300 . C12 C13 1.375(4) . C13 C14 1.374(3) . C13 H13 0.9300 . C14 H14 0.9300 . C15 C16 1.492(4) . C16 H16A 0.9600 . C16 H16B 0.9600 . C16 H16C 0.9600 . 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 C2 N2 N3 C1 0.1(3) C3 N2 N3 C1 177.3(2) N2 N3 C1 N1 0.0(3) C2 N1 C1 N3 0.0(3) Cu1 N1 C1 N3 -173.44(18) C1 N1 C2 N2 0.1(3) Cu1 N1 C2 N2 173.56(14) N3 N2 C2 N1 -0.1(3) C3 N2 C2 N1 -177.1(2) C9 O4 C3 N2 -84.6(2) C9 O4 C3 C4 153.44(18) C2 N2 C3 O4 -53.4(3) N3 N2 C3 O4 129.9(2) C2 N2 C3 C4 68.0(3) N3 N2 C3 C4 -108.7(2) O4 C3 C4 O3 66.3(2) N2 C3 C4 O3 -54.1(3) O4 C3 C4 C5 -61.6(3) N2 C3 C4 C5 178.0(2) O3 C4 C5 C8 67.2(3) C3 C4 C5 C8 -166.8(3) O3 C4 C5 C7 -51.5(3) C3 C4 C5 C7 74.5(3) O3 C4 C5 C6 -174.6(2) C3 C4 C5 C6 -48.5(3) C3 O4 C9 C10 -3.2(3) C3 O4 C9 C14 177.3(2) O4 C9 C10 C11 -178.3(2) C14 C9 C10 C11 1.1(4) C9 C10 C11 C12 -2.1(4) C10 C11 C12 C13 1.5(4) C10 C11 C12 Cl1 -177.05(19) C11 C12 C13 C14 0.2(4) Cl1 C12 C13 C14 178.7(2) C12 C13 C14 C9 -1.2(4) C10 C9 C14 C13 0.5(4) O4 C9 C14 C13 -180.0(2) Cu1 O2 C15 O1 -3.0(3) Cu1 O2 C15 C16 176.3(2)