#------------------------------------------------------------------------------ #$Date: 2020-04-28 01:37:23 +0300 (Tue, 28 Apr 2020) $ #$Revision: 251199 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240409.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_7240409 loop_ _publ_author_name 'Kusakawa, Takumi' 'Goto, Takayuki' 'Hori, Akiko' _publ_section_title ; Supramolecular association of M2+⋯\p induced by different electrostatic properties using naphthyl substituted \b-diketonate complexes (metal = Cu, Pd, Pt) ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00416B _journal_year 2020 _chemical_formula_moiety 'C46 H30 Cu O4' _chemical_formula_sum 'C46 H30 Cu O4' _chemical_formula_weight 710.24 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method 'APEX3 v2018.7-2' _audit_update_record ; 2020-02-18 deposited with the CCDC. 2020-04-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.070(11) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 13.093(7) _cell_length_b 5.920(4) _cell_length_c 21.808(12) _cell_measurement_reflns_used 187 _cell_measurement_temperature 100 _cell_measurement_theta_max 21.2077 _cell_measurement_theta_min 1.9129 _cell_volume 1653.0(17) _computing_cell_refinement 'APEX3 v2018.7-2 (Bruker AXS)' _computing_data_collection 'Bruker Instrument Service vV6.2.6' _computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 924)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 Goniometer' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1166 _diffrn_reflns_av_unetI/netI 0.0713 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 20850 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.97 _exptl_absorpt_coefficient_mu 0.709 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 734 _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.065 _exptl_crystal_size_min 0.047 _refine_diff_density_max 0.324 _refine_diff_density_min -0.404 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 232 _refine_ls_number_reflns 2901 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.078 _refine_ls_R_factor_all 0.0792 _refine_ls_R_factor_gt 0.0452 _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^)+(0.0304P)^2^+0.5990P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.1048 _reflns_number_gt 2071 _reflns_number_total 2901 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00416b2.cif _cod_data_source_block 'global_CCDC2' _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 1653.0(16) _cod_database_code 7240409 _shelx_shelxl_version_number 2016/6 _shelx_res_file ; TITL I2_a.res in P2(1)/n I2_a.res created by SHELXL-2018/3 at 12:36:49 on 18-Feb-2020 REM Old TITL I2 in I2 REM SHELXT solution in P2(1)/n REM R1 0.132, Rweak 0.004, Alpha 0.035, Orientation as input REM Formula found by SHELXT: C46 Cu O4 CELL 0.71073 13.0934 5.9201 21.8082 90.000 102.070 90.000 ZERR 2.000 0.0074 0.0035 0.0117 0.000 0.011 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H CU O UNIT 92 60 2 8 TEMP -173.130 L.S. 10 BOND $H LIST 6 size 0.047 0.065 0.130 shel 20 0.84 acta FMAP 2 PLAN 20 WGHT 0.030400 0.599000 FVAR 0.40873 C1 1 0.605581 -0.140007 0.315702 11.00000 0.01780 0.01615 = 0.02254 0.00240 -0.00138 -0.00070 AFIX 43 H1 2 0.615488 -0.236935 0.351172 11.00000 -1.20000 AFIX 0 C2 1 0.642431 -0.202644 0.263529 11.00000 0.01786 0.01894 = 0.02472 -0.00170 0.00300 0.00192 AFIX 43 H2 2 0.677050 -0.343593 0.263345 11.00000 -1.20000 AFIX 0 C3 1 0.629704 -0.060529 0.209896 11.00000 0.01411 0.01799 = 0.01982 -0.00223 0.00207 -0.00203 C4 1 0.666848 -0.121045 0.154953 11.00000 0.02065 0.01639 = 0.02849 -0.00360 0.00670 0.00050 AFIX 43 H4 2 0.702366 -0.260293 0.153591 11.00000 -1.20000 AFIX 0 C5 1 0.651384 0.021263 0.104182 11.00000 0.03234 0.02666 = 0.02704 -0.00755 0.01381 -0.00211 AFIX 43 H5 2 0.676073 -0.020900 0.067830 11.00000 -1.20000 AFIX 0 C6 1 0.599047 0.230370 0.105272 11.00000 0.03460 0.01946 = 0.02331 0.00146 0.01194 -0.00319 AFIX 43 H6 2 0.588543 0.326513 0.069625 11.00000 -1.20000 AFIX 0 C7 1 0.563592 0.294461 0.157360 11.00000 0.02616 0.02003 = 0.01889 0.00056 0.00802 -0.00172 AFIX 43 H7 2 0.529041 0.435404 0.157739 11.00000 -1.20000 AFIX 0 C8 1 0.578049 0.151551 0.211079 11.00000 0.01333 0.01961 = 0.01935 -0.00296 0.00163 -0.00538 C9 1 0.539956 0.210473 0.265069 11.00000 0.01705 0.01593 = 0.02278 -0.00047 0.00279 0.00143 AFIX 43 H9 2 0.504773 0.350484 0.265784 11.00000 -1.20000 AFIX 0 C10 1 0.552394 0.070678 0.316667 11.00000 0.01538 0.01620 = 0.01972 -0.00098 0.00056 -0.00164 C11 1 0.512164 0.128145 0.374763 11.00000 0.01923 0.01750 = 0.01585 0.00021 -0.00165 -0.00508 C12 1 0.457189 0.330514 0.378321 11.00000 0.02489 0.01631 = 0.01537 0.00503 0.00380 0.00109 AFIX 43 H12 2 0.450590 0.433959 0.344416 11.00000 -1.20000 AFIX 0 C13 1 0.411604 0.388528 0.428893 11.00000 0.01390 0.01745 = 0.01451 -0.00227 -0.00071 -0.00475 C14 1 0.344289 0.594965 0.426039 11.00000 0.01449 0.01516 = 0.01744 0.00183 0.00284 -0.00273 C15 1 0.306764 0.713016 0.371446 11.00000 0.01874 0.01914 = 0.01772 -0.00293 0.00473 -0.00161 AFIX 43 H15 2 0.324842 0.664143 0.333604 11.00000 -1.20000 AFIX 0 C16 1 0.241540 0.906517 0.370335 11.00000 0.01672 0.01945 = 0.01658 0.00267 0.00009 0.00006 C17 1 0.203654 1.031515 0.314525 11.00000 0.02033 0.02410 = 0.01850 0.00256 0.00315 0.00077 AFIX 43 H17 2 0.219501 0.982341 0.276106 11.00000 -1.20000 AFIX 0 C18 1 0.144580 1.221987 0.315492 11.00000 0.02014 0.02255 = 0.02280 0.00709 -0.00179 0.00309 AFIX 43 H18 2 0.120210 1.304640 0.277944 11.00000 -1.20000 AFIX 0 C19 1 0.119857 1.295634 0.372326 11.00000 0.01895 0.01482 = 0.02956 0.00135 0.00109 0.00287 AFIX 43 H19 2 0.079391 1.428564 0.372814 11.00000 -1.20000 AFIX 0 C20 1 0.153716 1.177088 0.426629 11.00000 0.02053 0.01886 = 0.02559 -0.00230 0.00480 -0.00017 AFIX 43 H20 2 0.136173 1.228510 0.464384 11.00000 -1.20000 AFIX 0 C21 1 0.214642 0.978490 0.427397 11.00000 0.01431 0.01759 = 0.01811 0.00148 0.00274 -0.00283 C22 1 0.254319 0.854182 0.482721 11.00000 0.01791 0.02488 = 0.01641 -0.00157 0.00482 -0.00066 AFIX 43 H22 2 0.237467 0.900992 0.521081 11.00000 -1.20000 AFIX 0 C23 1 0.316359 0.668218 0.482332 11.00000 0.02037 0.01789 = 0.01711 0.00084 0.00059 -0.00214 AFIX 43 H23 2 0.340997 0.587283 0.520148 11.00000 -1.20000 REM ##### AFIX 0 CU1 3 0.500000 0.000000 0.500000 10.50000 0.02177 0.01507 = 0.01515 0.00226 0.00142 0.00156 O1 4 0.531571 -0.021278 0.418298 11.00000 0.02404 0.01456 = 0.01698 0.00256 0.00243 0.00053 O2 4 0.421952 0.274815 0.479991 11.00000 0.02188 0.01730 = 0.01462 0.00367 0.00192 0.00147 HKLF 4 REM I2_a.res in P2(1)/n REM wR2 = 0.104808, GooF = S = 1.07780, Restrained GooF = 1.07780 for all data REM R1 = 0.045224 for 2071 Fo > 4sig(Fo) and 0.079239 for all 2901 data REM 232 parameters refined using 0 restraints END WGHT 0.0304 0.5990 REM Highest difference peak 0.324, deepest hole -0.404, 1-sigma level 0.077 Q1 1 0.4789 0.2548 0.4926 11.00000 0.05 0.32 Q2 1 0.5612 -0.0364 0.0096 11.00000 0.05 0.29 Q3 1 0.6038 -0.1563 0.2788 11.00000 0.05 0.28 Q4 1 0.5401 0.1419 0.2287 11.00000 0.05 0.28 Q5 1 0.6183 0.1375 0.4210 11.00000 0.05 0.27 Q6 1 0.5759 -0.0247 0.3185 11.00000 0.05 0.27 Q7 1 0.4671 0.3892 0.4088 11.00000 0.05 0.27 Q8 1 0.0186 1.1759 0.4630 11.00000 0.05 0.26 Q9 1 0.5196 0.0604 0.1013 11.00000 0.05 0.26 Q10 1 0.4266 0.7380 0.4794 11.00000 0.05 0.26 Q11 1 0.5609 0.4025 0.4192 11.00000 0.05 0.26 Q12 1 0.7602 -0.0040 0.1440 11.00000 0.05 0.25 Q13 1 0.4928 -0.2405 0.4222 11.00000 0.05 0.25 Q14 1 0.4026 0.3259 0.3908 11.00000 0.05 0.25 Q15 1 0.4129 0.3910 0.4925 11.00000 0.05 0.25 Q16 1 0.3372 1.0161 0.4453 11.00000 0.05 0.25 Q17 1 0.6136 0.1185 0.1125 11.00000 0.05 0.25 Q18 1 0.3244 1.0025 0.5832 11.00000 0.05 0.25 Q19 1 0.5776 -0.0915 0.4106 11.00000 0.05 0.24 Q20 1 0.5000 0.5000 0.5000 10.50000 0.05 0.24 ; _shelx_res_checksum 77343 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.6056(3) -0.1400(6) 0.31570(16) 0.0196(8) Uani d . . . 1 . . H H1 0.615488 -0.236935 0.351172 0.024 Uiso calc U . R 1 . . C C2 0.6424(3) -0.2026(6) 0.26353(16) 0.0207(8) Uani d . . . 1 . . H H2 0.67705 -0.343593 0.263345 0.025 Uiso calc U . R 1 . . C C3 0.6297(2) -0.0605(5) 0.20990(15) 0.0175(8) Uani d . . . 1 . . C C4 0.6668(3) -0.1210(6) 0.15495(16) 0.0216(8) Uani d . . . 1 . . H H4 0.702366 -0.260293 0.153591 0.026 Uiso calc U . R 1 . . C C5 0.6514(3) 0.0213(6) 0.10418(16) 0.0276(9) Uani d . . . 1 . . H H5 0.676073 -0.0209 0.06783 0.033 Uiso calc U . R 1 . . C C6 0.5990(3) 0.2304(6) 0.10527(17) 0.0249(9) Uani d . . . 1 . . H H6 0.588543 0.326513 0.069625 0.03 Uiso calc U . R 1 . . C C7 0.5636(3) 0.2945(6) 0.15736(15) 0.0212(8) Uani d . . . 1 . . H H7 0.529041 0.435404 0.157739 0.025 Uiso calc U . R 1 . . C C8 0.5780(2) 0.1516(6) 0.21108(15) 0.0177(8) Uani d . . . 1 . . C C9 0.5400(2) 0.2105(6) 0.26507(15) 0.0188(8) Uani d . . . 1 . . H H9 0.504773 0.350484 0.265784 0.023 Uiso calc U . R 1 . . C C10 0.5524(2) 0.0707(5) 0.31667(15) 0.0176(8) Uani d . . . 1 . . C C11 0.5122(3) 0.1281(6) 0.37476(15) 0.0183(8) Uani d . . . 1 . . C C12 0.4572(3) 0.3305(6) 0.37832(15) 0.0189(8) Uani d . . . 1 . . H H12 0.45059 0.433959 0.344416 0.023 Uiso calc U . R 1 . . C C13 0.4116(2) 0.3885(6) 0.42889(15) 0.0158(7) Uani d . . . 1 . . C C14 0.3443(2) 0.5950(6) 0.42604(15) 0.0158(7) Uani d . . . 1 . . C C15 0.3068(3) 0.7130(6) 0.37145(16) 0.0184(8) Uani d . . . 1 . . H H15 0.324842 0.664143 0.333604 0.022 Uiso calc U . R 1 . . C C16 0.2415(2) 0.9065(6) 0.37034(15) 0.0181(8) Uani d . . . 1 . . C C17 0.2037(2) 1.0315(6) 0.31452(15) 0.0211(8) Uani d . . . 1 . . H H17 0.219501 0.982341 0.276106 0.025 Uiso calc U . R 1 . . C C18 0.1446(3) 1.2220(6) 0.31549(16) 0.0227(8) Uani d . . . 1 . . H H18 0.12021 1.30464 0.277944 0.027 Uiso calc U . R 1 . . C C19 0.1199(3) 1.2956(6) 0.37233(16) 0.0217(8) Uani d . . . 1 . . H H19 0.079391 1.428564 0.372814 0.026 Uiso calc U . R 1 . . C C20 0.1537(3) 1.1771(6) 0.42663(16) 0.0217(8) Uani d . . . 1 . . H H20 0.136173 1.22851 0.464384 0.026 Uiso calc U . R 1 . . C C21 0.2146(2) 0.9785(6) 0.42740(14) 0.0168(7) Uani d . . . 1 . . C C22 0.2543(2) 0.8542(6) 0.48272(15) 0.0196(8) Uani d . . . 1 . . H H22 0.237467 0.900992 0.521081 0.023 Uiso calc U . R 1 . . C C23 0.3164(3) 0.6682(6) 0.48233(16) 0.0189(8) Uani d . . . 1 . . H H23 0.340997 0.587283 0.520148 0.023 Uiso calc U . R 1 . . Cu Cu1 0.5 0 0.5 0.01768(18) Uani d . P S 1 . . O O1 0.53157(16) -0.0213(4) 0.41830(9) 0.0188(5) Uani d . . . 1 . . O O2 0.42195(17) 0.2748(4) 0.47999(10) 0.0182(5) Uani d . . . 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 C1 0.0178(19) 0.0162(19) 0.023(2) -0.0007(15) -0.0014(15) 0.0024(15) C2 0.0179(19) 0.019(2) 0.025(2) 0.0019(15) 0.0030(16) -0.0017(16) C3 0.0141(17) 0.018(2) 0.0198(18) -0.0020(14) 0.0021(14) -0.0022(14) C4 0.0207(19) 0.0164(19) 0.028(2) 0.0005(16) 0.0067(16) -0.0036(16) C5 0.032(2) 0.027(2) 0.027(2) -0.0021(19) 0.0138(17) -0.0076(18) C6 0.035(2) 0.019(2) 0.023(2) -0.0032(17) 0.0119(18) 0.0015(16) C7 0.026(2) 0.020(2) 0.0189(19) -0.0017(16) 0.0080(16) 0.0006(15) C8 0.0133(18) 0.0196(19) 0.0193(19) -0.0054(15) 0.0016(15) -0.0030(15) C9 0.0170(19) 0.0159(19) 0.0228(19) 0.0014(15) 0.0028(15) -0.0005(15) C10 0.0154(18) 0.0162(19) 0.0197(19) -0.0016(14) 0.0006(15) -0.0010(14) C11 0.0192(19) 0.0175(19) 0.0158(18) -0.0051(16) -0.0017(15) 0.0002(15) C12 0.025(2) 0.0163(19) 0.0154(18) 0.0011(15) 0.0038(16) 0.0050(15) C13 0.0139(18) 0.0174(18) 0.0145(18) -0.0048(15) -0.0007(14) -0.0023(15) C14 0.0145(18) 0.0152(17) 0.0174(18) -0.0027(15) 0.0028(14) 0.0018(14) C15 0.0187(19) 0.0191(19) 0.0177(18) -0.0016(15) 0.0047(15) -0.0029(15) C16 0.0167(18) 0.0194(18) 0.0166(18) 0.0001(15) 0.0001(14) 0.0027(15) C17 0.0203(18) 0.024(2) 0.0185(18) 0.0008(16) 0.0032(14) 0.0026(16) C18 0.020(2) 0.023(2) 0.023(2) 0.0031(16) -0.0018(16) 0.0071(16) C19 0.0190(19) 0.0148(19) 0.030(2) 0.0029(15) 0.0011(16) 0.0014(16) C20 0.0205(19) 0.019(2) 0.026(2) -0.0002(16) 0.0048(16) -0.0023(16) C21 0.0143(17) 0.0176(18) 0.0181(17) -0.0028(16) 0.0027(14) 0.0015(16) C22 0.0179(19) 0.025(2) 0.0164(19) -0.0007(16) 0.0048(15) -0.0016(15) C23 0.0204(19) 0.0179(19) 0.0171(19) -0.0021(15) 0.0006(15) 0.0008(15) Cu1 0.0218(3) 0.0151(3) 0.0151(3) 0.0016(3) 0.0014(2) 0.0023(3) O1 0.0240(13) 0.0146(12) 0.0170(12) 0.0005(11) 0.0024(10) 0.0026(11) O2 0.0219(13) 0.0173(13) 0.0146(12) 0.0015(11) 0.0019(10) 0.0037(10) 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' Cu Cu 0.3201 1.2651 '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 C2 C1 C10 . . 120.2(3) ? C2 C1 H1 . . 119.9 ? C10 C1 H1 . . 119.9 ? C1 C2 C3 . . 121.3(3) ? C1 C2 H2 . . 119.4 ? C3 C2 H2 . . 119.4 ? C2 C3 C8 . . 118.7(3) ? C2 C3 C4 . . 122.6(3) ? C8 C3 C4 . . 118.7(3) ? C5 C4 C3 . . 120.2(3) ? C5 C4 H4 . . 119.9 ? C3 C4 H4 . . 119.9 ? C4 C5 C6 . . 120.9(3) ? C4 C5 H5 . . 119.6 ? C6 C5 H5 . . 119.6 ? C7 C6 C5 . . 120.4(3) ? C7 C6 H6 . . 119.8 ? C5 C6 H6 . . 119.8 ? C6 C7 C8 . . 120.5(3) ? C6 C7 H7 . . 119.7 ? C8 C7 H7 . . 119.7 ? C9 C8 C7 . . 121.9(3) ? C9 C8 C3 . . 118.8(3) ? C7 C8 C3 . . 119.3(3) ? C10 C9 C8 . . 121.9(3) ? C10 C9 H9 . . 119.0 ? C8 C9 H9 . . 119.0 ? C9 C10 C1 . . 119.1(3) ? C9 C10 C11 . . 123.2(3) ? C1 C10 C11 . . 117.7(3) ? O1 C11 C12 . . 124.7(3) ? O1 C11 C10 . . 114.6(3) ? C12 C11 C10 . . 120.7(3) ? C13 C12 C11 . . 123.9(3) ? C13 C12 H12 . . 118.0 ? C11 C12 H12 . . 118.0 ? O2 C13 C12 . . 124.7(3) ? O2 C13 C14 . . 114.7(3) ? C12 C13 C14 . . 120.7(3) ? C15 C14 C23 . . 118.8(3) ? C15 C14 C13 . . 123.3(3) ? C23 C14 C13 . . 117.9(3) ? C14 C15 C16 . . 121.7(3) ? C14 C15 H15 . . 119.1 ? C16 C15 H15 . . 119.1 ? C17 C16 C15 . . 122.2(3) ? C17 C16 C21 . . 119.0(3) ? C15 C16 C21 . . 118.8(3) ? C18 C17 C16 . . 120.8(3) ? C18 C17 H17 . . 119.6 ? C16 C17 H17 . . 119.6 ? C17 C18 C19 . . 120.1(3) ? C17 C18 H18 . . 120.0 ? C19 C18 H18 . . 120.0 ? C20 C19 C18 . . 120.6(3) ? C20 C19 H19 . . 119.7 ? C18 C19 H19 . . 119.7 ? C19 C20 C21 . . 121.0(3) ? C19 C20 H20 . . 119.5 ? C21 C20 H20 . . 119.5 ? C22 C21 C20 . . 123.1(3) ? C22 C21 C16 . . 118.3(3) ? C20 C21 C16 . . 118.5(3) ? C23 C22 C21 . . 121.7(3) ? C23 C22 H22 . . 119.2 ? C21 C22 H22 . . 119.2 ? C22 C23 C14 . . 120.7(3) ? C22 C23 H23 . . 119.6 ? C14 C23 H23 . . 119.6 ? O1 Cu1 O1 . 3_656 180.0 ? O1 Cu1 O2 . . 93.00(9) ? O1 Cu1 O2 3_656 . 87.00(9) ? O1 Cu1 O2 . 3_656 87.00(9) ? O1 Cu1 O2 3_656 3_656 93.00(9) ? O2 Cu1 O2 . 3_656 180.0 ? C11 O1 Cu1 . . 126.5(2) ? C13 O2 Cu1 . . 126.5(2) ? 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 C1 C2 . 1.376(5) ? C1 C10 . 1.431(5) ? C1 H1 . 0.95 ? C2 C3 . 1.422(5) ? C2 H2 . 0.95 ? C3 C8 . 1.429(5) ? C3 C4 . 1.430(5) ? C4 C5 . 1.372(5) ? C4 H4 . 0.95 ? C5 C6 . 1.418(5) ? C5 H5 . 0.95 ? C6 C7 . 1.368(5) ? C6 H6 . 0.95 ? C7 C8 . 1.425(5) ? C7 H7 . 0.95 ? C8 C9 . 1.415(5) ? C9 C10 . 1.379(4) ? C9 H9 . 0.95 ? C10 C11 . 1.509(5) ? C11 O1 . 1.284(4) ? C11 C12 . 1.408(5) ? C12 C13 . 1.402(4) ? C12 H12 . 0.95 ? C13 O2 . 1.285(4) ? C13 C14 . 1.500(5) ? C14 C15 . 1.379(4) ? C14 C23 . 1.420(4) ? C15 C16 . 1.426(5) ? C15 H15 . 0.95 ? C16 C17 . 1.422(4) ? C16 C21 . 1.427(4) ? C17 C18 . 1.370(5) ? C17 H17 . 0.95 ? C18 C19 . 1.414(5) ? C18 H18 . 0.95 ? C19 C20 . 1.368(5) ? C19 H19 . 0.95 ? C20 C21 . 1.419(5) ? C20 H20 . 0.95 ? C21 C22 . 1.416(4) ? C22 C23 . 1.369(5) ? C22 H22 . 0.95 ? C23 H23 . 0.95 ? Cu1 O1 . 1.916(2) ? Cu1 O1 3_656 1.916(2) ? Cu1 O2 . 1.922(2) ? Cu1 O2 3_656 1.922(2) ?