#------------------------------------------------------------------------------ #$Date: 2014-07-12 05:06:18 +0100 (Sat, 12 Jul 2014) $ #$Revision: 120112 $ #$URL: svn://www.crystallography.net/cod/cif/7/11/20/7112054.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_7112054 loop_ _publ_author_name 'Sunghee Kim' 'Maxime A. Siegler' 'Kenneth D. Karlin' _publ_section_title ; Peroxynitrite chemistry derived from nitric oxide reaction with a Cu(II)-OOH species and a copper mediated NO reductive coupling reaction ; _journal_name_full Chem.Commun. _journal_page_first 2844 _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C25 H25 Cu1 N6 O3, (Cl O4)' _chemical_formula_sum 'C25 H25 Cl Cu N6 O7' _chemical_formula_weight 620.50 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 111.662(12) _cell_angle_beta 94.591(10) _cell_angle_gamma 98.200(12) _cell_formula_units_Z 2 _cell_length_a 10.2366(15) _cell_length_b 11.5506(16) _cell_length_c 12.0967(12) _cell_measurement_reflns_used 6657 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 25.13 _cell_measurement_theta_min 1.83 _cell_volume 1301.9(3) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics 'SHELXTL v6.10 (Sheldrick, 2008)' _computing_publication_material 'SHELXTL v6.10 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 110(2) _diffrn_detector_area_resol_mean 15.989 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Goniometer KM4/Xcalibur, detector: Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _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 12794 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.83 _exptl_absorpt_coefficient_mu 0.999 _exptl_absorpt_correction_T_max 0.897 _exptl_absorpt_correction_T_min 0.832 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour blue-green _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'small block' _exptl_crystal_F_000 638 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.409 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 365 _refine_ls_number_reflns 4585 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0298 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.6334P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.0804 _reflns_number_gt 4040 _reflns_number_total 4585 _reflns_threshold_expression I>2\s(I) _iucr_refine_instructions_details ; TITL x0950a in P-1 CELL 0.71073 10.2366 11.5506 12.0967 111.662 94.591 98.200 ZERR 2 0.0015 0.0016 0.0012 0.012 0.010 0.012 LATT 1 SFAC C H Cl Cu N O UNIT 50 50 2 2 12 14 TEMP -163 ACTA HTAB BOND BOND $H CONF WPDB L.S. 6 FMAP 2 PLAN 10 OMIT -2 50 OMIT 0 1 0 OMIT 1 0 0 WGHT 0.043800 0.633400 FVAR 3.41103 PART 0 rem Cu complex CU1 4 0.029931 0.521205 0.212743 11.00000 0.00898 0.01411 = 0.01783 0.00626 0.00469 0.00165 C1 1 -0.042652 0.238779 0.092033 11.00000 0.01666 0.01994 = 0.02338 0.00776 0.00522 0.00439 AFIX 43 H1 2 0.050147 0.238176 0.093174 11.00000 -1.20000 AFIX 0 C2 1 -0.132114 0.126374 0.035386 11.00000 0.02567 0.01712 = 0.02592 0.00257 0.00431 0.00379 AFIX 43 H2 2 -0.101306 0.049405 -0.002579 11.00000 -1.20000 AFIX 0 C3 1 -0.268352 0.126738 0.034347 11.00000 0.02448 0.01748 = 0.02419 0.00095 0.00253 -0.00298 AFIX 43 H3 2 -0.331562 0.050292 -0.005061 11.00000 -1.20000 AFIX 0 C4 1 -0.310046 0.239938 0.091484 11.00000 0.01440 0.02190 = 0.02189 0.00524 0.00279 -0.00152 AFIX 43 H4 2 -0.402251 0.242429 0.093162 11.00000 -1.20000 AFIX 0 C5 1 -0.214994 0.349735 0.146280 11.00000 0.01397 0.02121 = 0.01565 0.00900 0.00414 0.00204 C6 1 -0.255017 0.476602 0.205641 11.00000 0.00941 0.01818 = 0.02085 0.00811 0.00292 -0.00001 AFIX 23 H6A 2 -0.292577 0.503992 0.143345 11.00000 -1.20000 H6B 2 -0.324790 0.468981 0.255989 11.00000 -1.20000 AFIX 0 C7 1 -0.145117 0.703026 0.287936 11.00000 0.01217 0.01629 = 0.02509 0.00980 0.00648 0.00541 AFIX 23 H7A 2 -0.179167 0.750332 0.362822 11.00000 -1.20000 H7B 2 -0.208771 0.697117 0.219155 11.00000 -1.20000 AFIX 0 C8 1 -0.011211 0.774372 0.285334 11.00000 0.01376 0.01806 = 0.01941 0.01068 0.00199 0.00216 C9 1 0.013677 0.904445 0.320090 11.00000 0.01930 0.01790 = 0.03564 0.00984 0.00654 0.00734 AFIX 43 H9 2 -0.051984 0.952697 0.352266 11.00000 -1.20000 AFIX 0 C10 1 0.135708 0.963437 0.307341 11.00000 0.02352 0.01549 = 0.04433 0.01103 0.00474 -0.00012 AFIX 43 H10 2 0.154467 1.052734 0.329907 11.00000 -1.20000 AFIX 0 C11 1 0.230151 0.891182 0.261431 11.00000 0.01595 0.02333 = 0.03499 0.01476 0.00352 -0.00252 AFIX 43 H11 2 0.314366 0.929954 0.251715 11.00000 -1.20000 AFIX 0 C12 1 0.200065 0.762719 0.230226 11.00000 0.01022 0.02257 = 0.02354 0.01261 0.00263 0.00059 AFIX 43 H12 2 0.265259 0.713076 0.199765 11.00000 -1.20000 AFIX 0 C13 1 -0.121476 0.569699 0.404728 11.00000 0.01343 0.01836 = 0.01617 0.00842 0.00624 0.00246 AFIX 23 H13A 2 -0.137433 0.480419 0.397393 11.00000 -1.20000 H13B 2 -0.188954 0.612036 0.450458 11.00000 -1.20000 AFIX 0 C14 1 0.016193 0.634696 0.472849 11.00000 0.01413 0.01617 = 0.01802 0.01114 0.00522 0.00271 C15 1 0.036511 0.733257 0.583812 11.00000 0.01788 0.01732 = 0.01892 0.00718 0.00633 0.00521 AFIX 43 H15 2 -0.036273 0.763644 0.622083 11.00000 -1.20000 AFIX 0 C16 1 0.169471 0.787163 0.638242 11.00000 0.02271 0.01385 = 0.01777 0.00402 0.00424 0.00194 AFIX 43 H16 2 0.187401 0.856730 0.713723 11.00000 -1.20000 AFIX 0 C17 1 0.272761 0.740074 0.583216 11.00000 0.01384 0.01777 = 0.01876 0.00692 0.00081 -0.00070 AFIX 43 H17 2 0.362453 0.776595 0.619619 11.00000 -1.20000 AFIX 0 C18 1 0.243901 0.635795 0.470878 11.00000 0.01212 0.01340 = 0.01712 0.00934 0.00302 -0.00005 C19 1 0.481602 0.625737 0.444587 11.00000 0.01126 0.02026 = 0.02190 0.00551 0.00347 0.00272 AFIX 23 H19A 2 0.530410 0.554364 0.418048 11.00000 -1.20000 H19B 2 0.505145 0.669616 0.532884 11.00000 -1.20000 AFIX 0 C20 1 0.526396 0.717712 0.385895 11.00000 0.00913 0.01948 = 0.02854 0.00858 0.00539 0.00410 C21 1 0.581384 0.843974 0.456243 11.00000 0.01992 0.02191 = 0.03145 0.00669 0.00991 0.00469 AFIX 43 H21 2 0.592979 0.872703 0.541415 11.00000 -1.20000 AFIX 0 C22 1 0.619263 0.927867 0.401601 11.00000 0.02334 0.01978 = 0.05207 0.01378 0.01360 0.00332 AFIX 43 H22 2 0.657441 1.013765 0.449703 11.00000 -1.20000 AFIX 0 C23 1 0.601735 0.887101 0.277706 11.00000 0.02019 0.03236 = 0.04978 0.02662 0.01261 0.00860 AFIX 43 H23 2 0.626736 0.945332 0.241123 11.00000 -1.20000 AFIX 0 C24 1 0.547566 0.760997 0.206383 11.00000 0.01468 0.04157 = 0.03292 0.02093 0.00679 0.01111 AFIX 43 H24 2 0.536115 0.732720 0.121246 11.00000 -1.20000 AFIX 0 C25 1 0.510396 0.676855 0.260924 11.00000 0.00922 0.02510 = 0.03017 0.01127 0.00480 0.00389 AFIX 43 H25 2 0.473726 0.590656 0.212605 11.00000 -1.20000 AFIX 0 N1 5 -0.083517 0.349993 0.146076 11.00000 0.01302 0.01698 = 0.01722 0.00657 0.00283 0.00216 N2 5 -0.137550 0.573012 0.281757 11.00000 0.01113 0.01313 = 0.01601 0.00580 0.00306 0.00159 N3 5 0.080995 0.704524 0.241349 11.00000 0.01223 0.01706 = 0.01786 0.00981 0.00372 0.00219 N4 5 0.115565 0.586782 0.415434 11.00000 0.01237 0.01284 = 0.01697 0.00754 0.00363 0.00062 DFIX 0.88 0.03 N5 H5 N5 5 0.338370 0.575455 0.415437 11.00000 0.01135 0.01647 = 0.01794 0.00176 0.00244 -0.00025 H5 2 0.313809 0.520248 0.345735 11.00000 0.01789 N6 5 0.212502 0.445526 0.052116 11.00000 0.01518 0.02241 = 0.01911 0.00812 0.00513 0.00407 O1 6 0.200143 0.474404 0.164910 11.00000 0.01512 0.02259 = 0.01425 0.00571 0.00542 0.00535 O2 6 0.113052 0.431019 -0.019422 11.00000 0.01834 0.07749 = 0.02405 0.02421 -0.00107 0.00496 O3 6 0.323463 0.435983 0.021916 11.00000 0.02001 0.04375 = 0.02624 0.01383 0.01243 0.01178 rem counterion CL1 3 0.345899 0.226439 0.213620 11.00000 0.01431 0.01552 = 0.02912 0.00595 0.00284 -0.00026 O4 6 0.415217 0.132036 0.229885 11.00000 0.02475 0.01992 = 0.04104 0.01277 0.00034 0.00302 O5 6 0.246853 0.250932 0.292582 11.00000 0.02746 0.03627 = 0.06134 0.02004 0.02599 0.00493 O6 6 0.440470 0.341673 0.242597 11.00000 0.01842 0.01502 = 0.03618 0.00642 0.00779 -0.00105 O7 6 0.282688 0.181343 0.090669 11.00000 0.04667 0.02615 = 0.03475 0.00188 -0.01326 0.00612 HKLF 4 REM x0950a in P-1 REM R1 = 0.0298 for 4040 Fo > 4sig(Fo) and 0.0357 for all 4585 data REM 365 parameters refined using 1 restraints END WGHT 0.0438 0.6340 REM Highest difference peak 0.409, deepest hole -0.458, 1-sigma level 0.063 Q1 1 -0.0370 0.4285 0.1631 11.00000 0.05 0.41 Q2 1 0.3509 0.2323 0.3018 11.00000 0.05 0.38 Q3 1 0.0901 0.6205 0.2608 11.00000 0.05 0.35 Q4 1 0.0470 0.5770 0.3267 11.00000 0.05 0.34 Q5 1 0.0300 0.4980 0.1199 11.00000 0.05 0.32 Q6 1 0.2475 0.1581 0.1472 11.00000 0.05 0.32 Q7 1 -0.1310 0.5790 0.3460 11.00000 0.05 0.31 Q8 1 0.1736 0.6021 0.4412 11.00000 0.05 0.31 Q9 1 -0.0443 0.6106 0.4398 11.00000 0.05 0.31 Q10 1 0.0260 0.7047 0.5102 11.00000 0.05 0.29 ; _[local]_cod_data_source_file c3cc47942k.txt _[local]_cod_data_source_block '[(BA)Cu(NO3)](ClO4)' _cod_database_code 7112054 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags Cu1 Cu 0.02993(2) 0.52121(2) 0.21274(2) 0.01350(9) Uani 1 1 d . C1 C -0.0427(2) 0.2388(2) 0.0920(2) 0.0199(5) Uani 1 1 d . H1 H 0.0501 0.2382 0.0932 0.024 Uiso 1 1 calc R C2 C -0.1321(2) 0.1264(2) 0.0354(2) 0.0246(5) Uani 1 1 d . H2 H -0.1013 0.0494 -0.0026 0.029 Uiso 1 1 calc R C3 C -0.2684(2) 0.1267(2) 0.0343(2) 0.0249(5) Uani 1 1 d . H3 H -0.3316 0.0503 -0.0051 0.030 Uiso 1 1 calc R C4 C -0.3100(2) 0.2399(2) 0.0915(2) 0.0208(5) Uani 1 1 d . H4 H -0.4023 0.2424 0.0932 0.025 Uiso 1 1 calc R C5 C -0.2150(2) 0.3497(2) 0.1463(2) 0.0164(4) Uani 1 1 d . C6 C -0.25502(19) 0.4766(2) 0.2056(2) 0.0162(5) Uani 1 1 d . H6A H -0.2926 0.5040 0.1433 0.019 Uiso 1 1 calc R H6B H -0.3248 0.4690 0.2560 0.019 Uiso 1 1 calc R C7 C -0.1451(2) 0.7030(2) 0.2879(2) 0.0168(5) Uani 1 1 d . H7A H -0.1792 0.7503 0.3628 0.020 Uiso 1 1 calc R H7B H -0.2088 0.6971 0.2192 0.020 Uiso 1 1 calc R C8 C -0.0112(2) 0.7744(2) 0.2853(2) 0.0162(5) Uani 1 1 d . C9 C 0.0137(2) 0.9044(2) 0.3201(2) 0.0239(5) Uani 1 1 d . H9 H -0.0520 0.9527 0.3523 0.029 Uiso 1 1 calc R C10 C 0.1357(2) 0.9634(2) 0.3073(2) 0.0283(6) Uani 1 1 d . H10 H 0.1545 1.0527 0.3299 0.034 Uiso 1 1 calc R C11 C 0.2302(2) 0.8912(2) 0.2614(2) 0.0244(5) Uani 1 1 d . H11 H 0.3144 0.9300 0.2517 0.029 Uiso 1 1 calc R C12 C 0.2001(2) 0.7627(2) 0.2302(2) 0.0179(5) Uani 1 1 d . H12 H 0.2653 0.7131 0.1998 0.022 Uiso 1 1 calc R C13 C -0.1215(2) 0.5697(2) 0.40473(19) 0.0153(4) Uani 1 1 d . H13A H -0.1374 0.4804 0.3974 0.018 Uiso 1 1 calc R H13B H -0.1890 0.6120 0.4505 0.018 Uiso 1 1 calc R C14 C 0.0162(2) 0.6347(2) 0.4728(2) 0.0146(4) Uani 1 1 d . C15 C 0.0365(2) 0.7333(2) 0.5838(2) 0.0176(5) Uani 1 1 d . H15 H -0.0363 0.7636 0.6221 0.021 Uiso 1 1 calc R C16 C 0.1695(2) 0.7872(2) 0.6382(2) 0.0188(5) Uani 1 1 d . H16 H 0.1874 0.8567 0.7137 0.023 Uiso 1 1 calc R C17 C 0.2728(2) 0.7401(2) 0.5832(2) 0.0173(5) Uani 1 1 d . H17 H 0.3625 0.7766 0.6196 0.021 Uiso 1 1 calc R C18 C 0.24390(19) 0.63580(19) 0.47088(19) 0.0134(4) Uani 1 1 d . C19 C 0.4816(2) 0.6257(2) 0.4446(2) 0.0185(5) Uani 1 1 d . H19A H 0.5304 0.5544 0.4180 0.022 Uiso 1 1 calc R H19B H 0.5051 0.6696 0.5329 0.022 Uiso 1 1 calc R C20 C 0.5264(2) 0.7177(2) 0.3859(2) 0.0189(5) Uani 1 1 d . C21 C 0.5814(2) 0.8440(2) 0.4562(2) 0.0250(5) Uani 1 1 d . H21 H 0.5930 0.8727 0.5414 0.030 Uiso 1 1 calc R C22 C 0.6193(2) 0.9279(2) 0.4016(3) 0.0313(6) Uani 1 1 d . H22 H 0.6574 1.0138 0.4497 0.038 Uiso 1 1 calc R C23 C 0.6017(2) 0.8871(2) 0.2777(3) 0.0301(6) Uani 1 1 d . H23 H 0.6267 0.9453 0.2411 0.036 Uiso 1 1 calc R C24 C 0.5476(2) 0.7610(2) 0.2064(2) 0.0270(6) Uani 1 1 d . H24 H 0.5361 0.7327 0.1212 0.032 Uiso 1 1 calc R C25 C 0.5104(2) 0.6769(2) 0.2609(2) 0.0211(5) Uani 1 1 d . H25 H 0.4737 0.5907 0.2126 0.025 Uiso 1 1 calc R N1 N -0.08352(17) 0.34999(17) 0.14608(16) 0.0158(4) Uani 1 1 d . N2 N -0.13755(16) 0.57301(16) 0.28176(16) 0.0134(4) Uani 1 1 d . N3 N 0.08099(16) 0.70452(17) 0.24135(16) 0.0148(4) Uani 1 1 d . N4 N 0.11557(16) 0.58678(16) 0.41543(16) 0.0136(4) Uani 1 1 d . N5 N 0.33837(17) 0.57546(18) 0.41544(18) 0.0170(4) Uani 1 1 d D H5 H 0.314(2) 0.520(2) 0.3457(19) 0.018(7) Uiso 1 1 d D N6 N 0.21250(17) 0.44553(18) 0.05212(17) 0.0186(4) Uani 1 1 d . O1 O 0.20014(14) 0.47440(14) 0.16491(13) 0.0173(3) Uani 1 1 d . O2 O 0.11305(16) 0.4310(2) -0.01942(16) 0.0393(5) Uani 1 1 d . O3 O 0.32346(16) 0.43598(17) 0.02192(15) 0.0287(4) Uani 1 1 d . Cl1 Cl 0.34590(5) 0.22644(5) 0.21362(5) 0.02077(14) Uani 1 1 d . O4 O 0.41522(16) 0.13204(15) 0.22988(16) 0.0287(4) Uani 1 1 d . O5 O 0.24685(18) 0.25093(18) 0.29258(19) 0.0403(5) Uani 1 1 d . O6 O 0.44047(15) 0.34167(14) 0.24260(15) 0.0244(4) Uani 1 1 d . O7 O 0.28269(19) 0.18134(17) 0.09067(17) 0.0399(5) Uani 1 1 d . 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 0.00898(14) 0.01411(15) 0.01783(17) 0.00626(12) 0.00469(10) 0.00165(10) C1 0.0167(11) 0.0199(12) 0.0234(13) 0.0078(10) 0.0052(9) 0.0044(9) C2 0.0257(12) 0.0171(12) 0.0259(14) 0.0026(10) 0.0043(10) 0.0038(9) C3 0.0245(12) 0.0175(12) 0.0242(14) 0.0010(10) 0.0025(10) -0.0030(9) C4 0.0144(10) 0.0219(12) 0.0219(13) 0.0052(10) 0.0028(9) -0.0015(9) C5 0.0140(10) 0.0212(12) 0.0157(12) 0.0090(10) 0.0041(8) 0.0020(9) C6 0.0094(9) 0.0182(11) 0.0209(12) 0.0081(10) 0.0029(8) 0.0000(8) C7 0.0122(10) 0.0163(11) 0.0251(13) 0.0098(10) 0.0065(9) 0.0054(8) C8 0.0138(10) 0.0181(11) 0.0194(12) 0.0107(10) 0.0020(9) 0.0022(8) C9 0.0193(11) 0.0179(12) 0.0356(15) 0.0098(11) 0.0065(10) 0.0073(9) C10 0.0235(12) 0.0155(12) 0.0443(17) 0.0110(11) 0.0047(11) -0.0001(9) C11 0.0160(11) 0.0233(12) 0.0350(15) 0.0148(11) 0.0035(10) -0.0025(9) C12 0.0102(10) 0.0226(12) 0.0235(13) 0.0126(10) 0.0026(9) 0.0006(8) C13 0.0134(10) 0.0184(11) 0.0162(12) 0.0084(10) 0.0062(8) 0.0025(8) C14 0.0141(10) 0.0162(11) 0.0180(12) 0.0111(10) 0.0052(8) 0.0027(8) C15 0.0179(11) 0.0173(11) 0.0189(13) 0.0072(10) 0.0063(9) 0.0052(9) C16 0.0227(11) 0.0139(11) 0.0178(12) 0.0040(10) 0.0042(9) 0.0019(9) C17 0.0138(10) 0.0178(11) 0.0188(12) 0.0069(10) 0.0008(9) -0.0007(8) C18 0.0121(10) 0.0134(10) 0.0171(12) 0.0093(9) 0.0030(8) 0.0000(8) C19 0.0113(10) 0.0203(12) 0.0219(13) 0.0055(10) 0.0035(9) 0.0027(8) C20 0.0091(10) 0.0195(11) 0.0285(14) 0.0086(10) 0.0054(9) 0.0041(8) C21 0.0199(11) 0.0219(12) 0.0315(15) 0.0067(11) 0.0099(10) 0.0047(9) C22 0.0233(12) 0.0198(13) 0.0521(19) 0.0138(12) 0.0136(12) 0.0033(10) C23 0.0202(12) 0.0324(14) 0.0498(18) 0.0266(13) 0.0126(11) 0.0086(10) C24 0.0147(11) 0.0416(15) 0.0329(15) 0.0209(13) 0.0068(10) 0.0111(10) C25 0.0092(10) 0.0251(12) 0.0302(14) 0.0113(11) 0.0048(9) 0.0039(9) N1 0.0130(8) 0.0170(9) 0.0172(10) 0.0066(8) 0.0028(7) 0.0022(7) N2 0.0111(8) 0.0131(9) 0.0160(10) 0.0058(8) 0.0031(7) 0.0016(7) N3 0.0122(8) 0.0171(9) 0.0179(10) 0.0098(8) 0.0037(7) 0.0022(7) N4 0.0124(8) 0.0128(9) 0.0170(10) 0.0075(8) 0.0036(7) 0.0006(7) N5 0.0114(9) 0.0165(10) 0.0179(11) 0.0018(9) 0.0024(8) -0.0002(7) N6 0.0152(9) 0.0224(10) 0.0191(11) 0.0081(8) 0.0051(8) 0.0041(8) O1 0.0151(7) 0.0226(8) 0.0143(9) 0.0057(7) 0.0054(6) 0.0054(6) O2 0.0183(9) 0.0775(15) 0.0241(10) 0.0242(10) -0.0011(7) 0.0050(9) O3 0.0200(8) 0.0437(11) 0.0262(10) 0.0138(8) 0.0124(7) 0.0118(7) Cl1 0.0143(3) 0.0155(3) 0.0291(3) 0.0059(2) 0.0028(2) -0.0003(2) O4 0.0247(9) 0.0199(9) 0.0410(11) 0.0128(8) 0.0003(8) 0.0030(7) O5 0.0275(9) 0.0363(11) 0.0613(14) 0.0200(10) 0.0260(9) 0.0049(8) O6 0.0184(8) 0.0150(8) 0.0362(10) 0.0064(7) 0.0078(7) -0.0011(6) O7 0.0467(12) 0.0262(10) 0.0347(12) 0.0019(9) -0.0133(9) 0.0061(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O1 Cu1 N1 99.02(7) O1 Cu1 N3 96.18(7) N1 Cu1 N3 156.35(7) O1 Cu1 N2 173.46(6) N1 Cu1 N2 82.82(7) N3 Cu1 N2 84.12(7) O1 Cu1 N4 90.90(6) N1 Cu1 N4 113.18(7) N3 Cu1 N4 84.47(7) N2 Cu1 N4 82.62(7) N1 C1 C2 121.7(2) N1 C1 H1 119.1 C2 C1 H1 119.1 C1 C2 C3 119.3(2) C1 C2 H2 120.3 C3 C2 H2 120.3 C4 C3 C2 119.0(2) C4 C3 H3 120.5 C2 C3 H3 120.5 C3 C4 C5 118.8(2) C3 C4 H4 120.6 C5 C4 H4 120.6 N1 C5 C4 122.3(2) N1 C5 C6 116.55(19) C4 C5 C6 121.07(19) N2 C6 C5 110.39(16) N2 C6 H6A 109.6 C5 C6 H6A 109.6 N2 C6 H6B 109.6 C5 C6 H6B 109.6 H6A C6 H6B 108.1 N2 C7 C8 111.77(16) N2 C7 H7A 109.3 C8 C7 H7A 109.3 N2 C7 H7B 109.3 C8 C7 H7B 109.3 H7A C7 H7B 107.9 N3 C8 C9 121.48(19) N3 C8 C7 116.62(18) C9 C8 C7 121.80(19) C8 C9 C10 119.0(2) C8 C9 H9 120.5 C10 C9 H9 120.5 C11 C10 C9 119.4(2) C11 C10 H10 120.3 C9 C10 H10 120.3 C12 C11 C10 118.8(2) C12 C11 H11 120.6 C10 C11 H11 120.6 N3 C12 C11 122.1(2) N3 C12 H12 118.9 C11 C12 H12 118.9 N2 C13 C14 111.76(16) N2 C13 H13A 109.3 C14 C13 H13A 109.3 N2 C13 H13B 109.3 C14 C13 H13B 109.3 H13A C13 H13B 107.9 N4 C14 C15 123.74(19) N4 C14 C13 113.76(19) C15 C14 C13 122.50(19) C14 C15 C16 117.4(2) C14 C15 H15 121.3 C16 C15 H15 121.3 C17 C16 C15 120.5(2) C17 C16 H16 119.8 C15 C16 H16 119.8 C16 C17 C18 118.9(2) C16 C17 H17 120.5 C18 C17 H17 120.5 N5 C18 N4 116.08(19) N5 C18 C17 123.04(19) N4 C18 C17 120.80(19) N5 C19 C20 112.86(17) N5 C19 H19A 109.0 C20 C19 H19A 109.0 N5 C19 H19B 109.0 C20 C19 H19B 109.0 H19A C19 H19B 107.8 C21 C20 C25 119.4(2) C21 C20 C19 120.4(2) C25 C20 C19 120.2(2) C22 C21 C20 119.9(2) C22 C21 H21 120.1 C20 C21 H21 120.1 C23 C22 C21 120.4(2) C23 C22 H22 119.8 C21 C22 H22 119.8 C22 C23 C24 120.2(2) C22 C23 H23 119.9 C24 C23 H23 119.9 C25 C24 C23 119.4(2) C25 C24 H24 120.3 C23 C24 H24 120.3 C24 C25 C20 120.7(2) C24 C25 H25 119.7 C20 C25 H25 119.7 C5 N1 C1 118.81(19) C5 N1 Cu1 114.39(14) C1 N1 Cu1 126.48(15) C6 N2 C7 112.82(15) C6 N2 C13 109.68(16) C7 N2 C13 111.28(16) C6 N2 Cu1 108.40(13) C7 N2 Cu1 109.33(12) C13 N2 Cu1 105.00(11) C8 N3 C12 119.21(18) C8 N3 Cu1 114.40(14) C12 N3 Cu1 126.13(15) C14 N4 C18 118.59(19) C14 N4 Cu1 103.37(13) C18 N4 Cu1 129.06(14) C18 N5 C19 124.90(19) C18 N5 H5 116.6(17) C19 N5 H5 114.7(17) O3 N6 O2 122.81(19) O3 N6 O1 118.49(17) O2 N6 O1 118.69(17) N6 O1 Cu1 116.37(12) O5 Cl1 O6 108.91(11) O5 Cl1 O7 109.58(12) O6 Cl1 O7 110.17(11) O5 Cl1 O4 109.76(11) O6 Cl1 O4 108.83(9) O7 Cl1 O4 109.57(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cu1 O1 1.9652(14) Cu1 N1 1.9818(18) Cu1 N3 1.9977(18) Cu1 N2 2.0365(17) Cu1 N4 2.3344(18) C1 N1 1.353(3) C1 C2 1.377(3) C1 H1 0.9500 C2 C3 1.394(3) C2 H2 0.9500 C3 C4 1.382(3) C3 H3 0.9500 C4 C5 1.385(3) C4 H4 0.9500 C5 N1 1.346(3) C5 C6 1.507(3) C6 N2 1.489(3) C6 H6A 0.9900 C6 H6B 0.9900 C7 N2 1.489(3) C7 C8 1.504(3) C7 H7A 0.9900 C7 H7B 0.9900 C8 N3 1.344(3) C8 C9 1.381(3) C9 C10 1.384(3) C9 H9 0.9500 C10 C11 1.383(3) C10 H10 0.9500 C11 C12 1.370(3) C11 H11 0.9500 C12 N3 1.347(3) C12 H12 0.9500 C13 N2 1.499(3) C13 C14 1.511(3) C13 H13A 0.9900 C13 H13B 0.9900 C14 N4 1.347(3) C14 C15 1.379(3) C15 C16 1.409(3) C15 H15 0.9500 C16 C17 1.366(3) C16 H16 0.9500 C17 C18 1.418(3) C17 H17 0.9500 C18 N5 1.350(3) C18 N4 1.365(3) C19 N5 1.461(3) C19 C20 1.521(3) C19 H19A 0.9900 C19 H19B 0.9900 C20 C21 1.393(3) C20 C25 1.395(3) C21 C22 1.390(3) C21 H21 0.9500 C22 C23 1.383(4) C22 H22 0.9500 C23 C24 1.392(4) C23 H23 0.9500 C24 C25 1.390(3) C24 H24 0.9500 C25 H25 0.9500 N5 H5 0.84(2) N6 O3 1.228(2) N6 O2 1.232(2) N6 O1 1.301(2) Cl1 O5 1.4345(18) Cl1 O6 1.4371(16) Cl1 O7 1.4422(19) Cl1 O4 1.4450(16) 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 C1 C2 C3 -0.5(4) C1 C2 C3 C4 -0.7(4) C2 C3 C4 C5 1.0(4) C3 C4 C5 N1 -0.2(3) C3 C4 C5 C6 177.5(2) N1 C5 C6 N2 -15.6(3) C4 C5 C6 N2 166.55(19) N2 C7 C8 N3 20.1(3) N2 C7 C8 C9 -163.3(2) N3 C8 C9 C10 1.0(4) C7 C8 C9 C10 -175.3(2) C8 C9 C10 C11 -0.7(4) C9 C10 C11 C12 -0.3(4) C10 C11 C12 N3 0.9(4) N2 C13 C14 N4 -56.6(2) N2 C13 C14 C15 123.9(2) N4 C14 C15 C16 1.0(3) C13 C14 C15 C16 -179.46(19) C14 C15 C16 C17 -1.7(3) C15 C16 C17 C18 -0.3(3) C16 C17 C18 N5 -173.54(19) C16 C17 C18 N4 3.1(3) N5 C19 C20 C21 116.9(2) N5 C19 C20 C25 -61.8(3) C25 C20 C21 C22 0.2(3) C19 C20 C21 C22 -178.58(19) C20 C21 C22 C23 0.5(3) C21 C22 C23 C24 -0.9(3) C22 C23 C24 C25 0.5(3) C23 C24 C25 C20 0.2(3) C21 C20 C25 C24 -0.6(3) C19 C20 C25 C24 178.19(18) C4 C5 N1 C1 -1.0(3) C6 C5 N1 C1 -178.85(19) C4 C5 N1 Cu1 172.85(17) C6 C5 N1 Cu1 -5.0(2) C2 C1 N1 C5 1.4(3) C2 C1 N1 Cu1 -171.70(17) O1 Cu1 N1 C5 -169.58(15) N3 Cu1 N1 C5 -40.2(3) N2 Cu1 N1 C5 16.77(15) N4 Cu1 N1 C5 95.54(15) O1 Cu1 N1 C1 3.76(19) N3 Cu1 N1 C1 133.1(2) N2 Cu1 N1 C1 -169.89(19) N4 Cu1 N1 C1 -91.12(19) C5 C6 N2 C7 148.57(18) C5 C6 N2 C13 -86.8(2) C5 C6 N2 Cu1 27.34(19) C8 C7 N2 C6 -141.02(18) C8 C7 N2 C13 95.2(2) C8 C7 N2 Cu1 -20.3(2) C14 C13 N2 C6 162.65(17) C14 C13 N2 C7 -71.8(2) C14 C13 N2 Cu1 46.36(18) N1 Cu1 N2 C6 -24.19(13) N3 Cu1 N2 C6 136.04(13) N4 Cu1 N2 C6 -138.79(13) N1 Cu1 N2 C7 -147.55(14) N3 Cu1 N2 C7 12.69(13) N4 Cu1 N2 C7 97.85(14) N1 Cu1 N2 C13 92.97(13) N3 Cu1 N2 C13 -106.79(13) N4 Cu1 N2 C13 -21.63(12) C9 C8 N3 C12 -0.4(3) C7 C8 N3 C12 176.11(18) C9 C8 N3 Cu1 174.10(17) C7 C8 N3 Cu1 -9.4(2) C11 C12 N3 C8 -0.6(3) C11 C12 N3 Cu1 -174.39(17) O1 Cu1 N3 C8 -175.59(15) N1 Cu1 N3 C8 54.6(3) N2 Cu1 N3 C8 -2.17(15) N4 Cu1 N3 C8 -85.29(15) O1 Cu1 N3 C12 -1.50(18) N1 Cu1 N3 C12 -131.3(2) N2 Cu1 N3 C12 171.92(19) N4 Cu1 N3 C12 88.80(18) C15 C14 N4 C18 1.7(3) C13 C14 N4 C18 -177.84(17) C15 C14 N4 Cu1 -148.37(18) C13 C14 N4 Cu1 32.04(18) N5 C18 N4 C14 173.08(17) C17 C18 N4 C14 -3.8(3) N5 C18 N4 Cu1 -45.5(2) C17 C18 N4 Cu1 137.56(17) O1 Cu1 N4 C14 175.68(13) N1 Cu1 N4 C14 -84.11(14) N3 Cu1 N4 C14 79.56(13) N2 Cu1 N4 C14 -5.21(13) O1 Cu1 N4 C18 29.97(17) N1 Cu1 N4 C18 130.18(17) N3 Cu1 N4 C18 -66.15(17) N2 Cu1 N4 C18 -150.92(17) N4 C18 N5 C19 166.70(19) C17 C18 N5 C19 -16.5(3) C20 C19 N5 C18 -81.9(3) O3 N6 O1 Cu1 168.28(15) O2 N6 O1 Cu1 -10.5(2) N1 Cu1 O1 N6 75.82(14) N3 Cu1 O1 N6 -86.00(14) N4 Cu1 O1 N6 -170.54(14) _journal_paper_doi 10.1039/c3cc47942k