#------------------------------------------------------------------------------ #$Date: 2018-01-16 04:34:49 +0200 (Tue, 16 Jan 2018) $ #$Revision: 205237 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229979.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_7229979 loop_ _publ_author_name 'Dankhoff, Katja' 'Weber, Birgit' _publ_section_title ; Novel Cu(II) complexes with NNO-Schiff base-like ligands -- structures and magnetic properties ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE02007D _journal_year 2018 _chemical_formula_moiety 'C32 H40 Cu2 N4 O12, 2(H2 O)' _chemical_formula_sum 'C32 H44 Cu2 N4 O14' _chemical_formula_weight 835.78 _chemical_name_common '[CuL30cOAc]' _chemical_name_systematic ; ? ; _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 mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2017-07-27 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-01-11 deposited with the CCDC. 2018-01-15 downloaded from the CCDC. ; _cell_angle_alpha 94.241(5) _cell_angle_beta 104.942(5) _cell_angle_gamma 108.277(5) _cell_formula_units_Z 1 _cell_length_a 8.8660(6) _cell_length_b 8.8511(6) _cell_length_c 12.7620(8) _cell_measurement_reflns_used 9512 _cell_measurement_temperature 133(2) _cell_measurement_theta_max 26.61 _cell_measurement_theta_min 1.68 _cell_volume 905.63(11) _computing_cell_refinement X-AREA-STOE _computing_data_collection X-AREA-STOE _computing_data_reduction X-AREA-STOE _computing_molecular_graphics ORTEP-III _computing_publication_material PLATON _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_solution SIR97 _diffrn_ambient_temperature 133(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.921 _diffrn_measurement_device_type STOE-STADIVARI _diffrn_measurement_method omega-scan _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_Laue_measured_fraction_full 0.977 _diffrn_reflns_Laue_measured_fraction_max 0.921 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 10553 _diffrn_reflns_point_group_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.921 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.601 _diffrn_reflns_theta_min 1.676 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 1.247 _exptl_absorpt_correction_type none _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 434 _exptl_crystal_size_max 0.169 _exptl_crystal_size_mid 0.107 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.541 _refine_diff_density_min -0.771 _refine_diff_density_rms 0.103 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 243 _refine_ls_number_reflns 4267 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.140 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0309 _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^)+(0.0612P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0867 _refine_ls_wR_factor_ref 0.1040 _reflns_number_gt 3604 _reflns_number_total 4267 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce02007d2.cif _cod_data_source_block cl123 _cod_database_code 7229979 _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_res_file ; shelx.res created by SHELXL-2014/7 TITL SIR97 run in space group P -1 CELL 0.71073 8.8660 8.8511 12.7620 94.241 104.942 108.277 ZERR 2.00 0.0006 0.0006 0.0008 0.005 0.005 0.005 LATT 1 SFAC C H N O CU UNIT 32 44 4 14 2 MERG 2 FMAP 2 PLAN 10 ACTA BOND $H CONF LIST 4 L.S. 20 TEMP -140.00 WGHT 0.061200 FVAR 0.56053 C1 1 0.563999 0.246678 0.327647 11.00000 0.02166 0.01593 = 0.01691 0.00329 0.00507 0.00442 AFIX 43 H1 2 0.640264 0.354435 0.346084 11.00000 -1.20000 AFIX 0 C2 1 0.553787 0.149972 0.234015 11.00000 0.02499 0.02477 = 0.01742 0.00306 0.00730 0.01145 AFIX 43 H2 2 0.621588 0.190191 0.188469 11.00000 -1.20000 AFIX 0 C3 1 0.442071 -0.007230 0.208252 11.00000 0.02534 0.02337 = 0.01565 -0.00142 0.00342 0.01227 AFIX 43 H3 2 0.433189 -0.076444 0.144706 11.00000 -1.20000 AFIX 0 C4 1 0.343634 -0.063002 0.275275 11.00000 0.02247 0.01490 = 0.01588 -0.00227 0.00179 0.00635 AFIX 43 H4 2 0.266351 -0.170240 0.258337 11.00000 -1.20000 AFIX 0 C5 1 0.360116 0.041199 0.368042 11.00000 0.01776 0.01305 = 0.01325 0.00177 0.00192 0.00625 C6 1 0.255135 -0.009599 0.443537 11.00000 0.01902 0.01202 = 0.01576 -0.00229 0.00280 0.00014 AFIX 23 H6A 2 0.137097 -0.029184 0.404127 11.00000 -1.20000 H6B 2 0.263866 -0.111169 0.467530 11.00000 -1.20000 AFIX 0 C7 1 0.241061 0.087872 0.616755 11.00000 0.01446 0.01228 = 0.01520 0.00283 0.00392 0.00294 AFIX 43 H7 2 0.155180 -0.013898 0.604247 11.00000 -1.20000 AFIX 0 C8 1 0.276950 0.189674 0.716906 11.00000 0.02031 0.01286 = 0.01302 0.00162 0.00302 0.00354 C9 1 0.417535 0.335982 0.748608 11.00000 0.01927 0.01340 = 0.01228 -0.00116 -0.00046 0.00627 C10 1 0.620872 0.540742 0.893721 11.00000 0.02276 0.01516 = 0.01525 -0.00348 0.00193 -0.00147 AFIX 23 H10A 2 0.622535 0.605673 0.960864 11.00000 -1.20000 H10B 2 0.632109 0.611274 0.837423 11.00000 -1.20000 AFIX 0 C11 1 0.764135 0.479514 0.919585 11.00000 0.02574 0.02666 = 0.03539 -0.00309 -0.00658 0.00526 AFIX 133 H11A 2 0.743370 0.395733 0.965442 11.00000 -1.50000 H11B 2 0.866682 0.568835 0.959228 11.00000 -1.50000 H11C 2 0.775786 0.434042 0.850954 11.00000 -1.50000 AFIX 0 C12 1 0.177508 0.134860 0.791200 11.00000 0.01746 0.01578 = 0.01414 0.00137 0.00157 0.00243 C13 1 0.000311 -0.096101 0.838782 11.00000 0.03105 0.02173 = 0.02225 0.00182 0.01269 -0.00008 AFIX 23 H13A 2 -0.085177 -0.201240 0.800234 11.00000 -1.20000 H13B 2 -0.057235 -0.023247 0.857559 11.00000 -1.20000 AFIX 0 C14 1 0.111073 -0.119515 0.942038 11.00000 0.05158 0.03316 = 0.03031 0.01465 0.01890 0.01886 AFIX 133 H14A 2 0.169893 -0.189625 0.923200 11.00000 -1.50000 H14B 2 0.043693 -0.169605 0.988497 11.00000 -1.50000 H14C 2 0.192088 -0.014630 0.981959 11.00000 -1.50000 AFIX 0 C21 1 0.807473 0.511939 0.577046 11.00000 0.01530 0.01381 = 0.01576 -0.00226 0.00266 0.00379 C22 1 0.944366 0.657696 0.567853 11.00000 0.01636 0.01419 = 0.03082 0.00423 0.00285 0.00085 AFIX 133 H22A 2 1.049224 0.666752 0.621858 11.00000 -1.50000 H22B 2 0.917174 0.754862 0.582114 11.00000 -1.50000 H22C 2 0.955840 0.646388 0.493600 11.00000 -1.50000 AFIX 0 N1 3 0.468699 0.192469 0.393739 11.00000 0.01744 0.01334 = 0.01333 -0.00031 0.00207 0.00502 N2 3 0.312226 0.117415 0.539373 11.00000 0.01657 0.01148 = 0.01203 -0.00065 0.00255 0.00139 O1 4 0.502771 0.397104 0.687979 11.00000 0.02173 0.01276 = 0.01263 0.00017 0.00339 -0.00002 O2 4 0.463103 0.406143 0.853032 11.00000 0.02175 0.02041 = 0.01297 -0.00326 0.00354 -0.00144 O3 4 0.163057 0.218546 0.865021 11.00000 0.02721 0.01911 = 0.01994 0.00118 0.01019 0.00574 O4 4 0.096757 -0.027565 0.767163 11.00000 0.03119 0.01533 = 0.01896 0.00013 0.01127 -0.00181 O21 4 0.657935 0.507750 0.531060 11.00000 0.01415 0.01231 = 0.01672 0.00169 0.00232 0.00093 O22 4 0.836390 0.401671 0.623465 11.00000 0.02144 0.01533 = 0.03267 0.00663 0.00245 0.00543 O31 4 1.155956 0.524713 0.784330 11.00000 0.02909 0.02672 = 0.04282 0.01148 -0.00224 0.00546 CU1 5 0.479749 0.315352 0.535910 11.00000 0.01530 0.00894 = 0.01155 -0.00013 0.00240 0.00097 H31A 2 1.067121 0.485305 0.748845 11.00000 0.05429 H31B 2 1.169743 0.458883 0.815773 11.00000 0.05826 HKLF 4 REM SIR97 run in space group P -1 REM R1 = 0.0309 for 3604 Fo > 4sig(Fo) and 0.0397 for all 4267 data REM 243 parameters refined using 0 restraints END WGHT 0.0612 0.0000 REM Highest difference peak 0.541, deepest hole -0.771, 1-sigma level 0.103 Q1 1 0.5774 0.3897 0.5531 11.00000 0.05 0.54 Q2 1 0.3801 0.2251 0.5167 11.00000 0.05 0.52 Q3 1 0.3140 0.0210 0.4075 11.00000 0.05 0.50 Q4 1 0.4678 0.2331 0.4453 11.00000 0.05 0.48 Q5 1 0.8693 0.5903 0.5778 11.00000 0.05 0.47 Q6 1 0.2407 0.1554 0.7621 11.00000 0.05 0.45 Q7 1 0.5378 0.2124 0.3690 11.00000 0.05 0.45 Q8 1 0.5422 0.3107 0.5025 11.00000 0.05 0.44 Q9 1 0.3968 0.3603 0.5664 11.00000 0.05 0.41 Q10 1 0.5177 0.3948 0.6325 11.00000 0.05 0.39 ; _shelx_res_checksum 66095 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 C1 C 0.5640(3) 0.2467(3) 0.32765(18) 0.0188(4) Uani 1 1 d . . H1 H 0.6403 0.3544 0.3461 0.023 Uiso 1 1 calc R U C2 C 0.5538(3) 0.1500(3) 0.23402(19) 0.0215(5) Uani 1 1 d . . H2 H 0.6216 0.1902 0.1885 0.026 Uiso 1 1 calc R U C3 C 0.4421(3) -0.0072(3) 0.20825(19) 0.0213(5) Uani 1 1 d . . H3 H 0.4332 -0.0764 0.1447 0.026 Uiso 1 1 calc R U C4 C 0.3436(3) -0.0630(3) 0.27527(18) 0.0188(4) Uani 1 1 d . . H4 H 0.2664 -0.1702 0.2583 0.023 Uiso 1 1 calc R U C5 C 0.3601(3) 0.0412(3) 0.36804(17) 0.0150(4) Uani 1 1 d . . C6 C 0.2551(3) -0.0096(3) 0.44354(18) 0.0176(4) Uani 1 1 d . . H6A H 0.1371 -0.0292 0.4041 0.021 Uiso 1 1 calc R U H6B H 0.2639 -0.1112 0.4675 0.021 Uiso 1 1 calc R U C7 C 0.2411(3) 0.0879(3) 0.61675(17) 0.0145(4) Uani 1 1 d . . H7 H 0.1552 -0.0139 0.6042 0.017 Uiso 1 1 calc R U C8 C 0.2770(3) 0.1897(3) 0.71691(17) 0.0164(4) Uani 1 1 d . . C9 C 0.4175(3) 0.3360(3) 0.74861(17) 0.0160(4) Uani 1 1 d . . C10 C 0.6209(3) 0.5407(3) 0.89372(18) 0.0208(5) Uani 1 1 d . . H10A H 0.6225 0.6057 0.9609 0.025 Uiso 1 1 calc R U H10B H 0.6321 0.6113 0.8374 0.025 Uiso 1 1 calc R U C11 C 0.7641(4) 0.4795(3) 0.9196(2) 0.0338(6) Uani 1 1 d . . H11A H 0.7434 0.3957 0.9654 0.051 Uiso 1 1 calc R U H11B H 0.8667 0.5688 0.9592 0.051 Uiso 1 1 calc R U H11C H 0.7758 0.4340 0.8510 0.051 Uiso 1 1 calc R U C12 C 0.1775(3) 0.1349(3) 0.79120(18) 0.0173(4) Uani 1 1 d . . C13 C 0.0003(4) -0.0961(3) 0.8388(2) 0.0264(5) Uani 1 1 d . . H13A H -0.0852 -0.2012 0.8002 0.032 Uiso 1 1 calc R U H13B H -0.0572 -0.0232 0.8576 0.032 Uiso 1 1 calc R U C14 C 0.1111(4) -0.1195(4) 0.9420(2) 0.0355(7) Uani 1 1 d . . H14A H 0.1699 -0.1896 0.9232 0.053 Uiso 1 1 calc R U H14B H 0.0437 -0.1696 0.9885 0.053 Uiso 1 1 calc R U H14C H 0.1921 -0.0146 0.9820 0.053 Uiso 1 1 calc R U C21 C 0.8075(3) 0.5119(3) 0.57705(17) 0.0159(4) Uani 1 1 d . . C22 C 0.9444(3) 0.6577(3) 0.5679(2) 0.0223(5) Uani 1 1 d . . H22A H 1.0492 0.6668 0.6219 0.034 Uiso 1 1 calc R U H22B H 0.9172 0.7549 0.5821 0.034 Uiso 1 1 calc R U H22C H 0.9558 0.6464 0.4936 0.034 Uiso 1 1 calc R U N1 N 0.4687(2) 0.1925(2) 0.39374(15) 0.0154(4) Uani 1 1 d . . N2 N 0.3122(2) 0.1174(2) 0.53937(14) 0.0147(4) Uani 1 1 d . . O1 O 0.5028(2) 0.39710(19) 0.68798(12) 0.0176(3) Uani 1 1 d . . O2 O 0.4631(2) 0.4061(2) 0.85303(13) 0.0212(4) Uani 1 1 d . . O3 O 0.1631(2) 0.2185(2) 0.86502(14) 0.0221(4) Uani 1 1 d . . O4 O 0.0968(2) -0.0276(2) 0.76716(14) 0.0236(4) Uani 1 1 d . . O21 O 0.6579(2) 0.50775(18) 0.53106(12) 0.0158(3) Uani 1 1 d . . O22 O 0.8364(2) 0.4017(2) 0.62347(15) 0.0243(4) Uani 1 1 d . . O31 O 1.1560(3) 0.5247(3) 0.7843(2) 0.0362(5) Uani 1 1 d . . Cu1 Cu 0.47975(3) 0.31535(3) 0.53591(2) 0.01314(10) Uani 1 1 d . . H31A H 1.067(6) 0.485(6) 0.749(4) 0.054(13) Uiso 1 1 d . . H31B H 1.170(6) 0.459(6) 0.816(4) 0.058(14) 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 C1 0.0217(12) 0.0159(10) 0.0169(10) 0.0033(8) 0.0051(9) 0.0044(9) C2 0.0250(12) 0.0248(12) 0.0174(10) 0.0031(9) 0.0073(9) 0.0114(10) C3 0.0253(12) 0.0234(11) 0.0157(10) -0.0014(8) 0.0034(9) 0.0123(10) C4 0.0225(12) 0.0149(10) 0.0159(10) -0.0023(8) 0.0018(9) 0.0063(9) C5 0.0178(11) 0.0131(9) 0.0132(9) 0.0018(7) 0.0019(8) 0.0062(8) C6 0.0190(11) 0.0120(10) 0.0158(10) -0.0023(8) 0.0028(8) 0.0001(8) C7 0.0145(10) 0.0123(9) 0.0152(10) 0.0028(7) 0.0039(8) 0.0029(8) C8 0.0203(11) 0.0129(10) 0.0130(9) 0.0016(7) 0.0030(8) 0.0035(9) C9 0.0193(11) 0.0134(10) 0.0123(9) -0.0012(7) -0.0005(8) 0.0063(9) C10 0.0228(12) 0.0152(10) 0.0153(10) -0.0035(8) 0.0019(9) -0.0015(9) C11 0.0257(14) 0.0267(13) 0.0354(15) -0.0031(11) -0.0066(12) 0.0053(11) C12 0.0175(11) 0.0158(10) 0.0141(9) 0.0014(8) 0.0016(8) 0.0024(9) C13 0.0311(14) 0.0217(12) 0.0222(11) 0.0018(9) 0.0127(11) -0.0001(10) C14 0.0516(19) 0.0332(15) 0.0303(14) 0.0147(11) 0.0189(13) 0.0189(14) C21 0.0153(10) 0.0138(10) 0.0158(10) -0.0023(7) 0.0027(8) 0.0038(8) C22 0.0164(11) 0.0142(10) 0.0308(12) 0.0042(9) 0.0029(9) 0.0008(9) N1 0.0174(9) 0.0133(8) 0.0133(8) -0.0003(6) 0.0021(7) 0.0050(7) N2 0.0166(9) 0.0115(8) 0.0120(8) -0.0006(6) 0.0025(7) 0.0014(7) O1 0.0217(8) 0.0128(7) 0.0126(7) 0.0002(5) 0.0034(6) 0.0000(6) O2 0.0217(9) 0.0204(8) 0.0130(7) -0.0033(6) 0.0035(6) -0.0014(7) O3 0.0272(9) 0.0191(8) 0.0199(8) 0.0012(6) 0.0102(7) 0.0057(7) O4 0.0312(10) 0.0153(8) 0.0190(8) 0.0001(6) 0.0113(7) -0.0018(7) O21 0.0141(8) 0.0123(7) 0.0167(7) 0.0017(5) 0.0023(6) 0.0009(6) O22 0.0214(9) 0.0153(8) 0.0327(9) 0.0066(7) 0.0025(7) 0.0054(7) O31 0.0291(12) 0.0267(10) 0.0428(12) 0.0115(9) -0.0022(10) 0.0055(9) Cu1 0.01530(15) 0.00894(13) 0.01155(14) -0.00013(9) 0.00240(10) 0.00097(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' 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' Cu Cu 0.3201 1.2651 '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_3 N1 C1 C2 122.0(2) . N1 C1 H1 119.0 . C2 C1 H1 119.0 . C1 C2 C3 118.4(2) . C1 C2 H2 120.8 . C3 C2 H2 120.8 . C4 C3 C2 119.9(2) . C4 C3 H3 120.1 . C2 C3 H3 120.1 . C3 C4 C5 118.7(2) . C3 C4 H4 120.7 . C5 C4 H4 120.7 . N1 C5 C4 121.7(2) . N1 C5 C6 116.58(18) . C4 C5 C6 121.7(2) . N2 C6 C5 109.39(18) . N2 C6 H6A 109.8 . C5 C6 H6A 109.8 . N2 C6 H6B 109.8 . C5 C6 H6B 109.8 . H6A C6 H6B 108.2 . N2 C7 C8 127.4(2) . N2 C7 H7 116.3 . C8 C7 H7 116.3 . C7 C8 C9 119.9(2) . C7 C8 C12 118.6(2) . C9 C8 C12 121.23(19) . O1 C9 O2 118.8(2) . O1 C9 C8 125.45(19) . O2 C9 C8 115.7(2) . O2 C10 C11 110.5(2) . O2 C10 H10A 109.6 . C11 C10 H10A 109.6 . O2 C10 H10B 109.6 . C11 C10 H10B 109.6 . H10A C10 H10B 108.1 . C10 C11 H11A 109.5 . C10 C11 H11B 109.5 . H11A C11 H11B 109.5 . C10 C11 H11C 109.5 . H11A C11 H11C 109.5 . H11B C11 H11C 109.5 . O3 C12 O4 121.9(2) . O3 C12 C8 126.6(2) . O4 C12 C8 111.41(19) . O4 C13 C14 110.3(2) . O4 C13 H13A 109.6 . C14 C13 H13A 109.6 . O4 C13 H13B 109.6 . C14 C13 H13B 109.6 . H13A C13 H13B 108.1 . C13 C14 H14A 109.5 . C13 C14 H14B 109.5 . H14A C14 H14B 109.5 . C13 C14 H14C 109.5 . H14A C14 H14C 109.5 . H14B C14 H14C 109.5 . O22 C21 O21 122.3(2) . O22 C21 C22 122.2(2) . O21 C21 C22 115.5(2) . C21 C22 H22A 109.5 . C21 C22 H22B 109.5 . H22A C22 H22B 109.5 . C21 C22 H22C 109.5 . H22A C22 H22C 109.5 . H22B C22 H22C 109.5 . C5 N1 C1 119.44(19) . C5 N1 Cu1 114.42(15) . C1 N1 Cu1 126.07(16) . C7 N2 C6 117.18(19) . C7 N2 Cu1 126.38(15) . C6 N2 Cu1 116.39(14) . C9 O1 Cu1 128.80(14) . C9 O2 C10 117.53(18) . C12 O4 C13 116.13(18) . C21 O21 Cu1 116.07(14) . C21 O21 Cu1 138.86(14) 2_666 Cu1 O21 Cu1 104.06(7) 2_666 H31A O31 H31B 102(5) . N2 Cu1 O21 176.39(8) . N2 Cu1 O1 90.70(7) . O21 Cu1 O1 90.92(7) . N2 Cu1 N1 82.78(8) . O21 Cu1 N1 95.03(7) . O1 Cu1 N1 167.67(7) . N2 Cu1 O21 107.23(7) 2_666 O21 Cu1 O21 75.94(7) 2_666 O1 Cu1 O21 91.51(6) 2_666 N1 Cu1 O21 100.39(7) 2_666 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 N1 1.352(3) . C1 C2 1.383(3) . C1 H1 0.9500 . C2 C3 1.388(4) . C2 H2 0.9500 . C3 C4 1.384(3) . C3 H3 0.9500 . C4 C5 1.392(3) . C4 H4 0.9500 . C5 N1 1.338(3) . C5 C6 1.504(3) . C6 N2 1.462(3) . C6 H6A 0.9900 . C6 H6B 0.9900 . C7 N2 1.303(3) . C7 C8 1.410(3) . C7 H7 0.9500 . C8 C9 1.430(3) . C8 C12 1.464(3) . C9 O1 1.253(3) . C9 O2 1.329(3) . C10 O2 1.461(3) . C10 C11 1.503(4) . C10 H10A 0.9900 . C10 H10B 0.9900 . C11 H11A 0.9800 . C11 H11B 0.9800 . C11 H11C 0.9800 . C12 O3 1.213(3) . C12 O4 1.360(3) . C13 O4 1.447(3) . C13 C14 1.498(4) . C13 H13A 0.9900 . C13 H13B 0.9900 . C14 H14A 0.9800 . C14 H14B 0.9800 . C14 H14C 0.9800 . C21 O22 1.238(3) . C21 O21 1.292(3) . C21 C22 1.505(3) . C22 H22A 0.9800 . C22 H22B 0.9800 . C22 H22C 0.9800 . N1 Cu1 2.0085(18) . N2 Cu1 1.9211(19) . O1 Cu1 1.9563(15) . O21 Cu1 1.9438(16) . O21 Cu1 2.3518(16) 2_666 O31 H31A 0.75(5) . O31 H31B 0.75(5) . Cu1 O21 2.3518(16) 2_666 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 _geom_torsion_site_symmetry_4 N1 C1 C2 C3 -0.1(4) . C1 C2 C3 C4 0.5(4) . C2 C3 C4 C5 -0.3(4) . C3 C4 C5 N1 -0.3(3) . C3 C4 C5 C6 178.8(2) . N1 C5 C6 N2 -7.0(3) . C4 C5 C6 N2 173.8(2) . N2 C7 C8 C9 -7.8(4) . N2 C7 C8 C12 177.9(2) . C7 C8 C9 O1 10.7(4) . C12 C8 C9 O1 -175.1(2) . C7 C8 C9 O2 -166.0(2) . C12 C8 C9 O2 8.1(3) . C7 C8 C12 O3 -160.7(2) . C9 C8 C12 O3 25.1(4) . C7 C8 C12 O4 18.4(3) . C9 C8 C12 O4 -155.8(2) . C4 C5 N1 C1 0.7(3) . C6 C5 N1 C1 -178.5(2) . C4 C5 N1 Cu1 -176.53(17) . C6 C5 N1 Cu1 4.3(3) . C2 C1 N1 C5 -0.4(3) . C2 C1 N1 Cu1 176.39(17) . C8 C7 N2 C6 178.7(2) . C8 C7 N2 Cu1 -3.8(3) . C5 C6 N2 C7 -175.61(19) . C5 C6 N2 Cu1 6.7(2) . O2 C9 O1 Cu1 174.80(15) . C8 C9 O1 Cu1 -1.8(3) . O1 C9 O2 C10 -6.6(3) . C8 C9 O2 C10 170.4(2) . C11 C10 O2 C9 -79.0(3) . O3 C12 O4 C13 -3.5(3) . C8 C12 O4 C13 177.3(2) . C14 C13 O4 C12 -81.0(3) . O22 C21 O21 Cu1 -1.3(3) . C22 C21 O21 Cu1 177.09(15) . O22 C21 O21 Cu1 164.82(16) 2_666 C22 C21 O21 Cu1 -16.8(3) 2_666