#------------------------------------------------------------------------------ #$Date: 2021-08-20 00:42:20 +0300 (Fri, 20 Aug 2021) $ #$Revision: 268138 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/43/1564379.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_1564379 loop_ _publ_author_name 'Benk\'o, T\'imea' 'Luk\'acs, D\'avid' 'Frey, Krisztina' 'N\'emeth, Mikl\'os' 'M\'oricz, M\'arta M.' 'Liu, Dongyu' 'Kov\'ats, \'Eva' 'May, N\'ora V.' 'Vayssieres, Lionel' 'Li, Mingtao' 'Pap, J\'ozsef S.' _publ_section_title ; Redox-inactive metal single-site molecular complexes: a new generation of electrocatalysts for oxygen evolution? ; _journal_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/D1CY01087E _journal_year 2021 _chemical_formula_moiety 'C18 H14 Cu N5 O, Cl O4, C H4 O' _chemical_formula_sum 'C19 H18 Cl Cu N5 O6' _chemical_formula_weight 511.37 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2021-03-22 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-04-01 deposited with the CCDC. 2021-08-13 downloaded from the CCDC. ; _cell_angle_alpha 91.738(2) _cell_angle_beta 105.882(2) _cell_angle_gamma 95.876(2) _cell_formula_units_Z 2 _cell_length_a 7.8810(2) _cell_length_b 10.7847(3) _cell_length_c 12.0770(4) _cell_measurement_reflns_used 6187 _cell_measurement_temperature 100.00(10) _cell_measurement_theta_max 29.5700 _cell_measurement_theta_min 3.4960 _cell_volume 980.28(5) _computing_cell_refinement 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.5908 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.863 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -61.00 39.00 1.00 5.00 -- 11.04 -57.00 60.00 100 2 \w -22.00 50.00 1.00 5.00 -- 11.04 -93.00 -28.47 72 3 \w -17.00 84.00 1.00 5.00 -- 11.04 57.00-150.00 101 4 \w -13.00 85.00 1.00 5.00 -- 11.04 38.00 90.00 98 5 \w -42.00 15.00 1.00 5.00 -- -11.51 -77.00 -90.00 57 6 \w -44.00 21.00 1.00 5.00 -- -11.51 77.00-180.00 65 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0473492000 _diffrn_orient_matrix_UB_12 -0.0517836000 _diffrn_orient_matrix_UB_13 0.0174558000 _diffrn_orient_matrix_UB_21 -0.0297220000 _diffrn_orient_matrix_UB_22 0.0407250000 _diffrn_orient_matrix_UB_23 0.0360927000 _diffrn_orient_matrix_UB_31 -0.0758167000 _diffrn_orient_matrix_UB_32 0.0068999000 _diffrn_orient_matrix_UB_33 -0.0462076000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_unetI/netI 0.0469 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.863 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 13087 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.863 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.690 _diffrn_reflns_theta_min 3.123 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.302 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.86969 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'dark black' _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary black _exptl_crystal_density_diffrn 1.732 _exptl_crystal_description block _exptl_crystal_F_000 522 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.478 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.090 _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 357 _refine_ls_number_reflns 4791 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0390 _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^)+(0.0359P)^2^+0.8485P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0835 _refine_ls_wR_factor_ref 0.0923 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3901 _reflns_number_total 4791 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cy01087e2.cif _cod_data_source_block exp_1061 _cod_database_code 1564379 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'Cu Cl N5 O6 C18 H20' _chemical_oxdiff_usercomment 'PJ2021/2: Cu-ind-OH2 #1' _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. ; _diffrn_oxdiff_digest_frames ; 010a720b75f50a0e864ee4d446f9c37a6b00493cd7d ; _diffrn_oxdiff_digest_hkl ; 013642628c3d02a1395b9507cadefdf1c08de3 ; _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C9(H9) ; _shelx_res_file ; TITL exp_1061 exp_1061.res created by SHELXL-2018/3 at 21:39:10 on 22-Mar-2021 CELL 0.71073 7.881 10.7847 12.077 91.738 105.882 95.876 ZERR 2 0.0002 0.0003 0.0004 0.002 0.002 0.002 LATT 1 SFAC C H Cl Cu N O UNIT 38 36 2 2 10 12 L.S. 10 PLAN 20 fmap 2 53 acta REM REM REM WGHT 0.035900 0.848500 FVAR 0.44988 CU01 4 0.712316 0.351436 0.264754 11.00000 0.01869 0.01385 = 0.01274 0.00116 0.00426 0.00097 O1 6 0.754522 0.504246 0.367569 11.00000 0.02211 0.01601 = 0.01563 0.00180 0.00559 0.00442 H1A 2 0.745961 0.503634 0.438408 11.00000 0.07193 H1B 2 0.704205 0.552836 0.342464 11.00000 0.01441 N1 5 0.551173 0.323518 -0.022147 11.00000 0.01452 0.01306 = 0.01489 0.00075 0.00501 0.00235 N2 5 0.757829 0.451068 0.136727 11.00000 0.01589 0.01313 = 0.01387 0.00135 0.00497 0.00170 N3 5 0.569550 0.226615 0.156874 11.00000 0.01526 0.01404 = 0.01450 0.00104 0.00516 0.00140 N4 5 0.742237 0.235057 0.391493 11.00000 0.01497 0.01687 = 0.01520 0.00143 0.00483 0.00399 N5 5 0.514616 0.071554 0.286728 11.00000 0.01950 0.01688 = 0.01811 0.00250 0.00694 0.00237 C1 1 0.484040 0.120877 0.187509 11.00000 0.01322 0.01320 = 0.01951 -0.00035 0.00627 0.00383 C2 1 0.505076 0.237244 0.040603 11.00000 0.01447 0.01294 = 0.01609 -0.00082 0.00560 0.00486 C3 1 0.883001 0.550903 0.168649 11.00000 0.01475 0.01745 = 0.01503 -0.00082 0.00408 0.00338 H3 2 0.948655 0.565263 0.245425 11.00000 0.01932 C4 1 0.677315 0.425243 0.022711 11.00000 0.01451 0.01325 = 0.01619 0.00073 0.00627 0.00413 C5 1 0.367971 0.130481 -0.008256 11.00000 0.01490 0.01489 = 0.01976 0.00124 0.00702 0.00500 C6 1 0.718385 0.505090 -0.058432 11.00000 0.01724 0.01752 = 0.01268 0.00052 0.00531 0.00439 H6 2 0.665825 0.488322 -0.133277 11.00000 0.01094 C7 1 0.928099 0.631321 0.092517 11.00000 0.01382 0.01571 = 0.02278 0.00108 0.00613 0.00021 H7 2 1.014941 0.700752 0.121612 11.00000 0.01604 C8 1 0.652204 0.119231 0.381831 11.00000 0.01830 0.01904 = 0.01819 0.00190 0.00962 0.00365 C9 1 0.876088 0.268853 0.488503 11.00000 0.01797 0.01967 = 0.01735 0.00144 0.00539 0.00438 AFIX 43 H9 2 0.937102 0.348490 0.495445 11.00000 -1.20000 AFIX 0 C10 1 0.841445 0.607855 -0.024599 11.00000 0.01993 0.01526 = 0.01887 0.00433 0.01018 0.00493 H10 2 0.870375 0.658602 -0.078924 11.00000 0.02942 C11 1 0.270696 0.092631 -0.120544 11.00000 0.01759 0.01677 = 0.01839 0.00011 0.00509 0.00511 H11 2 0.285139 0.134901 -0.181220 11.00000 0.02080 C12 1 0.141895 -0.088201 -0.044453 11.00000 0.01814 0.01459 = 0.02998 0.00001 0.00719 0.00268 H12 2 0.060616 -0.160409 -0.058456 11.00000 0.01769 C13 1 0.156742 -0.019156 -0.136975 11.00000 0.01621 0.01945 = 0.01982 -0.00152 0.00190 0.00400 H13 2 0.094511 -0.047107 -0.211927 11.00000 0.01945 C14 1 0.239569 -0.049910 0.068130 11.00000 0.01883 0.01688 = 0.02052 0.00329 0.00844 0.00308 H14 2 0.231844 -0.092230 0.130842 11.00000 0.01007 C15 1 0.926374 0.191279 0.577338 11.00000 0.02319 0.02559 = 0.01844 0.00016 0.00248 0.00418 H15 2 1.021039 0.220306 0.638974 11.00000 0.02734 C16 1 0.352510 0.060072 0.083701 11.00000 0.01516 0.01533 = 0.01951 0.00082 0.00644 0.00598 C17 1 0.697397 0.037394 0.470879 11.00000 0.02505 0.01992 = 0.02282 0.00461 0.00775 0.00088 H17 2 0.636609 -0.040297 0.461793 11.00000 0.02724 C18 1 0.833889 0.073054 0.567986 11.00000 0.03080 0.02486 = 0.02026 0.00936 0.00454 0.00642 H18 2 0.868331 0.017852 0.626095 11.00000 0.02592 CL02 3 1.222176 0.346305 0.352141 11.00000 0.01807 0.02071 = 0.01403 0.00247 0.00507 0.00429 O2 6 1.052126 0.301724 0.272255 11.00000 0.01923 0.03487 = 0.02108 0.00042 0.00286 -0.00010 O3 6 1.265101 0.263551 0.443904 11.00000 0.03288 0.02927 = 0.02121 0.01137 0.00499 0.00775 O4 6 1.209190 0.469604 0.399861 11.00000 0.04326 0.02175 = 0.01937 -0.00161 0.00946 0.00890 O5 6 1.355926 0.356209 0.292076 11.00000 0.02060 0.03879 = 0.02682 0.00525 0.01280 0.00846 O6 6 0.577075 0.680992 0.263737 11.00000 0.02347 0.02290 = 0.01377 0.00251 0.00253 0.00531 C19 1 0.439485 0.724591 0.306080 11.00000 0.02596 0.02295 = 0.01947 -0.00016 0.00499 0.00527 H19A 2 0.328348 0.680193 0.268368 11.00000 0.03338 H19B 2 0.474293 0.715405 0.388287 11.00000 0.02599 H19C 2 0.431293 0.811142 0.292550 11.00000 0.03785 H6A 2 0.548843 0.681153 0.202608 11.00000 0.01329 HKLF 4 REM exp_1061 REM wR2 = 0.0923, GooF = S = 1.059, Restrained GooF = 1.059 for all data REM R1 = 0.0390 for 3901 Fo > 4sig(Fo) and 0.0546 for all 4791 data REM 357 parameters refined using 0 restraints END WGHT 0.0360 0.8451 REM Highest difference peak 0.478, deepest hole -0.458, 1-sigma level 0.090 Q1 1 0.4230 0.1815 0.0024 11.00000 0.05 0.48 Q2 1 0.7829 0.6424 -0.1821 11.00000 0.05 0.47 Q3 1 0.2886 0.0053 0.0576 11.00000 0.05 0.42 Q4 1 1.0818 0.3577 0.2993 11.00000 0.05 0.40 Q5 1 0.6034 0.3637 0.0001 11.00000 0.05 0.40 Q6 1 0.3199 0.0824 -0.0604 11.00000 0.05 0.40 Q7 1 0.7081 0.2767 0.3386 11.00000 0.05 0.39 Q8 1 0.5475 0.2243 0.0965 11.00000 0.05 0.39 Q9 1 0.7016 0.4397 0.0823 11.00000 0.05 0.38 Q10 1 0.1934 -0.0625 0.0047 11.00000 0.05 0.38 Q11 1 0.8741 0.5995 0.0363 11.00000 0.05 0.37 Q12 1 0.3602 0.0846 0.0378 11.00000 0.05 0.36 Q13 1 0.6631 0.4668 -0.0180 11.00000 0.05 0.35 Q14 1 0.2112 0.0226 -0.1062 11.00000 0.05 0.35 Q15 1 0.4899 0.3392 -0.0488 11.00000 0.05 0.35 Q16 1 0.5385 0.0160 0.2815 11.00000 0.05 0.35 Q17 1 0.6692 0.2438 0.2783 11.00000 0.05 0.35 Q18 1 0.4050 0.0793 0.1318 11.00000 0.05 0.35 Q19 1 0.1590 -0.1358 -0.0549 11.00000 0.05 0.35 Q20 1 1.3110 0.2242 0.4374 11.00000 0.05 0.34 ; _shelx_res_checksum 59043 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.291 _oxdiff_exptl_absorpt_empirical_full_min 0.846 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 _atom_site_disorder_assembly _atom_site_disorder_group Cu01 Cu 0.71232(4) 0.35144(3) 0.26475(2) 0.01518(10) Uani 1 1 d . . . . . O1 O 0.7545(3) 0.50425(18) 0.36757(17) 0.0177(4) Uani 1 1 d . . . . . H1A H 0.746(6) 0.504(4) 0.438(4) 0.072(14) Uiso 1 1 d . . . . . H1B H 0.704(4) 0.553(3) 0.342(2) 0.014(8) Uiso 1 1 d . . . . . N1 N 0.5512(3) 0.32352(18) -0.02215(16) 0.0139(4) Uani 1 1 d . . . . . N2 N 0.7578(3) 0.45107(18) 0.13673(16) 0.0141(4) Uani 1 1 d . . . . . N3 N 0.5696(3) 0.22661(18) 0.15687(16) 0.0144(4) Uani 1 1 d . . . . . N4 N 0.7422(3) 0.23506(19) 0.39149(16) 0.0154(4) Uani 1 1 d . . . . . N5 N 0.5146(3) 0.07155(19) 0.28673(17) 0.0178(4) Uani 1 1 d . . . . . C1 C 0.4840(3) 0.1209(2) 0.1875(2) 0.0148(5) Uani 1 1 d . . . . . C2 C 0.5051(3) 0.2372(2) 0.0406(2) 0.0140(5) Uani 1 1 d . . . . . C3 C 0.8830(3) 0.5509(2) 0.1686(2) 0.0157(5) Uani 1 1 d . . . . . H3 H 0.949(4) 0.565(3) 0.245(2) 0.019(7) Uiso 1 1 d . . . . . C4 C 0.6773(3) 0.4252(2) 0.0227(2) 0.0141(5) Uani 1 1 d . . . . . C5 C 0.3680(3) 0.1305(2) -0.0083(2) 0.0158(5) Uani 1 1 d . . . . . C6 C 0.7184(3) 0.5051(2) -0.0584(2) 0.0154(5) Uani 1 1 d . . . . . H6 H 0.666(3) 0.488(2) -0.133(2) 0.011(6) Uiso 1 1 d . . . . . C7 C 0.9281(3) 0.6313(2) 0.0925(2) 0.0173(5) Uani 1 1 d . . . . . H7 H 1.015(4) 0.701(3) 0.122(2) 0.016(7) Uiso 1 1 d . . . . . C8 C 0.6522(3) 0.1192(2) 0.3818(2) 0.0175(5) Uani 1 1 d . . . . . C9 C 0.8761(3) 0.2689(2) 0.4885(2) 0.0181(5) Uani 1 1 d . . . . . H9 H 0.937102 0.348490 0.495445 0.022 Uiso 1 1 calc R . . . . C10 C 0.8414(3) 0.6079(2) -0.0246(2) 0.0168(5) Uani 1 1 d . . . . . H10 H 0.870(4) 0.659(3) -0.079(3) 0.029(8) Uiso 1 1 d . . . . . C11 C 0.2707(3) 0.0926(2) -0.1205(2) 0.0174(5) Uani 1 1 d . . . . . H11 H 0.285(4) 0.135(3) -0.181(2) 0.021(7) Uiso 1 1 d . . . . . C12 C 0.1419(3) -0.0882(2) -0.0445(2) 0.0208(5) Uani 1 1 d . . . . . H12 H 0.061(4) -0.160(3) -0.058(2) 0.018(7) Uiso 1 1 d . . . . . C13 C 0.1567(3) -0.0192(2) -0.1370(2) 0.0190(5) Uani 1 1 d . . . . . H13 H 0.095(4) -0.047(3) -0.212(2) 0.019(7) Uiso 1 1 d . . . . . C14 C 0.2396(3) -0.0499(2) 0.0681(2) 0.0180(5) Uani 1 1 d . . . . . H14 H 0.232(3) -0.092(2) 0.131(2) 0.010(6) Uiso 1 1 d . . . . . C15 C 0.9264(4) 0.1913(3) 0.5773(2) 0.0230(6) Uani 1 1 d . . . . . H15 H 1.021(4) 0.220(3) 0.639(3) 0.027(8) Uiso 1 1 d . . . . . C16 C 0.3525(3) 0.0601(2) 0.0837(2) 0.0160(5) Uani 1 1 d . . . . . C17 C 0.6974(4) 0.0374(3) 0.4709(2) 0.0224(6) Uani 1 1 d . . . . . H17 H 0.637(4) -0.040(3) 0.462(2) 0.027(8) Uiso 1 1 d . . . . . C18 C 0.8339(4) 0.0731(3) 0.5680(2) 0.0254(6) Uani 1 1 d . . . . . H18 H 0.868(4) 0.018(3) 0.626(3) 0.026(8) Uiso 1 1 d . . . . . Cl02 Cl 1.22218(8) 0.34631(6) 0.35214(5) 0.01730(14) Uani 1 1 d . . . . . O2 O 1.0521(2) 0.30172(18) 0.27225(15) 0.0259(4) Uani 1 1 d . . . . . O3 O 1.2651(3) 0.26355(18) 0.44390(15) 0.0278(4) Uani 1 1 d . . . . . O4 O 1.2092(3) 0.46960(17) 0.39986(15) 0.0277(4) Uani 1 1 d . . . . . O5 O 1.3559(2) 0.35621(19) 0.29208(16) 0.0271(4) Uani 1 1 d . . . . . O6 O 0.5771(2) 0.68099(17) 0.26374(17) 0.0204(4) Uani 1 1 d . . . . . C19 C 0.4395(4) 0.7246(3) 0.3061(2) 0.0229(6) Uani 1 1 d . . . . . H19A H 0.328(4) 0.680(3) 0.268(3) 0.033(8) Uiso 1 1 d . . . . . H19B H 0.474(4) 0.715(3) 0.388(3) 0.026(8) Uiso 1 1 d . . . . . H19C H 0.431(4) 0.811(3) 0.293(3) 0.038(9) Uiso 1 1 d . . . . . H6A H 0.549(4) 0.681(3) 0.203(2) 0.013(8) Uiso 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 Cu01 0.01869(17) 0.01385(16) 0.01274(15) 0.00116(11) 0.00426(12) 0.00097(12) O1 0.0221(10) 0.0160(9) 0.0156(9) 0.0018(8) 0.0056(8) 0.0044(8) N1 0.0145(10) 0.0131(9) 0.0149(9) 0.0008(8) 0.0050(8) 0.0024(8) N2 0.0159(10) 0.0131(9) 0.0139(9) 0.0014(8) 0.0050(8) 0.0017(8) N3 0.0153(10) 0.0140(10) 0.0145(9) 0.0010(8) 0.0052(8) 0.0014(8) N4 0.0150(10) 0.0169(10) 0.0152(9) 0.0014(8) 0.0048(8) 0.0040(8) N5 0.0195(11) 0.0169(10) 0.0181(10) 0.0025(8) 0.0069(9) 0.0024(9) C1 0.0132(11) 0.0132(11) 0.0195(12) -0.0003(9) 0.0063(9) 0.0038(9) C2 0.0145(11) 0.0129(11) 0.0161(11) -0.0008(9) 0.0056(9) 0.0049(9) C3 0.0148(12) 0.0174(12) 0.0150(11) -0.0008(10) 0.0041(10) 0.0034(10) C4 0.0145(11) 0.0132(11) 0.0162(11) 0.0007(9) 0.0063(9) 0.0041(9) C5 0.0149(12) 0.0149(12) 0.0198(12) 0.0012(10) 0.0070(10) 0.0050(10) C6 0.0172(12) 0.0175(12) 0.0127(11) 0.0005(10) 0.0053(10) 0.0044(10) C7 0.0138(12) 0.0157(12) 0.0228(12) 0.0011(10) 0.0061(10) 0.0002(10) C8 0.0183(12) 0.0190(12) 0.0182(12) 0.0019(10) 0.0096(10) 0.0037(10) C9 0.0180(12) 0.0197(12) 0.0173(12) 0.0014(10) 0.0054(10) 0.0044(10) C10 0.0199(13) 0.0153(12) 0.0189(12) 0.0043(10) 0.0102(10) 0.0049(10) C11 0.0176(12) 0.0168(12) 0.0184(12) 0.0001(10) 0.0051(10) 0.0051(10) C12 0.0181(13) 0.0146(12) 0.0300(14) 0.0000(11) 0.0072(11) 0.0027(10) C13 0.0162(12) 0.0194(12) 0.0198(12) -0.0015(10) 0.0019(10) 0.0040(10) C14 0.0188(13) 0.0169(12) 0.0205(12) 0.0033(10) 0.0084(10) 0.0031(10) C15 0.0232(14) 0.0256(14) 0.0184(12) 0.0002(11) 0.0025(11) 0.0042(11) C16 0.0152(12) 0.0153(11) 0.0195(12) 0.0008(10) 0.0064(10) 0.0060(9) C17 0.0251(14) 0.0199(13) 0.0228(13) 0.0046(11) 0.0078(11) 0.0009(11) C18 0.0308(15) 0.0249(14) 0.0203(13) 0.0094(12) 0.0045(11) 0.0064(12) Cl02 0.0181(3) 0.0207(3) 0.0140(3) 0.0025(2) 0.0051(2) 0.0043(2) O2 0.0192(10) 0.0349(11) 0.0211(9) 0.0004(8) 0.0029(8) -0.0001(8) O3 0.0329(11) 0.0293(10) 0.0212(9) 0.0114(8) 0.0050(8) 0.0077(9) O4 0.0433(12) 0.0217(10) 0.0194(9) -0.0016(8) 0.0095(9) 0.0089(9) O5 0.0206(10) 0.0388(12) 0.0268(10) 0.0053(9) 0.0128(8) 0.0085(9) O6 0.0235(10) 0.0229(10) 0.0138(9) 0.0025(8) 0.0025(8) 0.0053(8) C19 0.0260(15) 0.0229(14) 0.0195(13) -0.0002(11) 0.0050(11) 0.0053(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu01 N2 91.03(8) . . ? O1 Cu01 N4 94.89(8) . . ? N3 Cu01 O1 154.28(9) . . ? N3 Cu01 N2 90.47(8) . . ? N3 Cu01 N4 91.74(8) . . ? N4 Cu01 N2 161.45(8) . . ? C2 N1 C4 123.5(2) . . ? C3 N2 Cu01 115.96(15) . . ? C3 N2 C4 118.4(2) . . ? C4 N2 Cu01 125.66(16) . . ? C1 N3 Cu01 123.43(16) . . ? C2 N3 Cu01 126.17(16) . . ? C2 N3 C1 109.09(19) . . ? C8 N4 Cu01 124.26(16) . . ? C9 N4 Cu01 116.95(16) . . ? C9 N4 C8 118.3(2) . . ? C1 N5 C8 122.9(2) . . ? N3 C1 C16 108.8(2) . . ? N5 C1 N3 128.9(2) . . ? N5 C1 C16 122.1(2) . . ? N1 C2 N3 128.4(2) . . ? N1 C2 C5 122.8(2) . . ? N3 C2 C5 108.8(2) . . ? N2 C3 C7 123.8(2) . . ? N1 C4 C6 115.8(2) . . ? N2 C4 N1 124.4(2) . . ? N2 C4 C6 119.9(2) . . ? C11 C5 C2 132.3(2) . . ? C11 C5 C16 121.1(2) . . ? C16 C5 C2 106.5(2) . . ? C10 C6 C4 121.1(2) . . ? C3 C7 C10 118.1(2) . . ? N4 C8 N5 124.5(2) . . ? N4 C8 C17 120.3(2) . . ? N5 C8 C17 115.2(2) . . ? N4 C9 C15 123.4(2) . . ? C6 C10 C7 118.7(2) . . ? C5 C11 C13 117.2(2) . . ? C13 C12 C14 121.6(2) . . ? C12 C13 C11 121.1(2) . . ? C16 C14 C12 117.1(2) . . ? C9 C15 C18 118.5(2) . . ? C5 C16 C1 106.7(2) . . ? C14 C16 C1 131.2(2) . . ? C14 C16 C5 121.9(2) . . ? C18 C17 C8 120.5(2) . . ? C17 C18 C15 119.1(2) . . ? O2 Cl02 O4 107.94(12) . . ? O3 Cl02 O2 110.13(11) . . ? O3 Cl02 O4 109.27(11) . . ? O5 Cl02 O2 109.56(11) . . ? O5 Cl02 O3 110.71(12) . . ? O5 Cl02 O4 109.18(12) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu01 O1 1.9764(18) . ? Cu01 N2 1.9998(19) . ? Cu01 N3 1.8859(19) . ? Cu01 N4 1.988(2) . ? N1 C2 1.302(3) . ? N1 C4 1.390(3) . ? N2 C3 1.353(3) . ? N2 C4 1.356(3) . ? N3 C1 1.377(3) . ? N3 C2 1.369(3) . ? N4 C8 1.357(3) . ? N4 C9 1.355(3) . ? N5 C1 1.298(3) . ? N5 C8 1.388(3) . ? C1 C16 1.475(3) . ? C2 C5 1.482(3) . ? C3 C7 1.374(3) . ? C4 C6 1.405(3) . ? C5 C11 1.388(3) . ? C5 C16 1.390(3) . ? C6 C10 1.368(3) . ? C7 C10 1.395(3) . ? C8 C17 1.405(4) . ? C9 C15 1.378(4) . ? C11 C13 1.402(3) . ? C12 C13 1.386(4) . ? C12 C14 1.393(4) . ? C14 C16 1.383(3) . ? C15 C18 1.388(4) . ? C17 C18 1.370(4) . ? Cl02 O2 1.4458(18) . ? Cl02 O3 1.4338(18) . ? Cl02 O4 1.4576(19) . ? Cl02 O5 1.4314(19) . ? O6 C19 1.432(3) . ?