#------------------------------------------------------------------------------ #$Date: 2019-02-22 03:58:51 +0200 (Fri, 22 Feb 2019) $ #$Revision: 213782 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/82/7058201.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_7058201 loop_ _publ_author_name 'Wang, Mei' 'Gao, Wei-Song' 'WANG, JINMIAO' 'Shi, Ning-Ning' 'Chen, Chengneng' 'Fan, Yuhua' _publ_section_title ; Electrocatalytic water oxidation studies of a tetranuclear Cu(II) complex with cubane-like core Cu4(µ3-O)4 ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/C8NJ06263C _journal_year 2019 _chemical_formula_moiety 'C32 H38 Cu4 N4 O12, 3(H2 O), 2(N O3)' _chemical_formula_sum 'C32 H44 Cu4 N6 O21' _chemical_formula_weight 1102.89 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-02-16 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-02-16 deposited with the CCDC. 2019-02-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 101.306(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.785(3) _cell_length_b 17.746(3) _cell_length_c 16.689(3) _cell_measurement_reflns_used 6139 _cell_measurement_temperature 173 _cell_measurement_theta_max 27.549 _cell_measurement_theta_min 2.423 _cell_volume 4003.4(13) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _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_temperature 173.0 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.992 _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 0.0439 _diffrn_reflns_av_unetI/netI 0.0403 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 17767 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.553 _diffrn_reflns_theta_min 1.894 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.190 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1333 before and 0.0577 after correction. The Ratio of minimum to maximum transmission is 0.6996. The \l/2 correction factor is 0.00150.' _exptl_crystal_colour blue _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 1.830 _exptl_crystal_description block _exptl_crystal_F_000 2248 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.423 _refine_diff_density_min -0.471 _refine_diff_density_rms 0.087 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 340 _refine_ls_number_reflns 4599 _refine_ls_number_restraints 57 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0361 _refine_ls_R_factor_gt 0.0282 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+1.4177P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.0764 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3891 _reflns_number_total 4599 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; mo_2017524-2017062208_0m.res created by SHELXL-2014/7 TITL mo_2017524-2017062208_0m_a.res in C2/c REM Old TITL mo_2017524-2017062208_0m in C2/c REM SHELXT solution in C2/c REM R1 0.094, Rweak 0.003, Alpha 0.038, Orientation as input REM Formula found by SHELXT: C19 N3 O2W Cu2 CELL 0.71073 13.785 17.7457 16.6887 90 101.306 90 ZERR 4 0.0026 0.0033 0.003 0 0.004 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H Cu N O UNIT 128 176 16 24 84 DFIX 0.86 O4 H4 SADI O6 N4 O8 N4 O10 N4 SADI O7 N3 O9 N3 O11 N3 SADI O8 O6 O6 O10 SADI O7 O9 O9 O11 ISOR 0.005 0.01 O9 N3 O11 O7 ISOR 0.006 0.012 O7 O6 O9 O8 N3 N4 O10 O11 L.S. 4 PLAN 20 SIZE 0.28 0.15 0.11 TEMP -100.15 CONN 5 $Cu BOND $H list 4 fmap 2 acta OMIT 8 4 3 OMIT 4 10 6 REM REM REM WGHT 0.038100 1.417700 FVAR 0.13870 CU2 3 0.408456 0.582607 0.806210 11.00000 0.01525 0.01452 = 0.01442 -0.00013 0.00035 -0.00040 CU1 3 0.406966 0.679831 0.664227 11.00000 0.01439 0.01506 = 0.01631 0.00183 -0.00028 -0.00021 O1 5 0.446682 0.687959 0.815760 11.00000 0.01480 0.01423 = 0.02047 -0.00233 0.00084 0.00182 O3 5 0.445378 0.575407 0.667101 11.00000 0.01501 0.01401 = 0.01798 -0.00144 0.00009 -0.00131 O5 5 0.265565 0.601739 0.770845 11.00000 0.01762 0.02304 = 0.02261 0.00066 0.00244 -0.00012 O4 5 0.391248 0.530210 0.929447 11.00000 0.03184 0.02271 = 0.01856 -0.00114 0.00510 -0.00192 O0AA 5 0.264503 0.661060 0.652021 11.00000 0.01560 0.02615 = 0.02688 0.00451 -0.00143 -0.00184 O2 5 0.391148 0.728617 0.533867 11.00000 0.02835 0.02717 = 0.02302 0.00382 0.00301 -0.00111 N2 4 0.388200 0.474128 0.779465 11.00000 0.01452 0.01776 = 0.01631 -0.00027 0.00100 -0.00076 N1 4 0.386083 0.787425 0.683089 11.00000 0.01237 0.01718 = 0.02340 0.00149 -0.00220 0.00103 AFIX 6 O1W 5 0.560731 0.712413 0.477035 11.00000 0.04416 0.05109 = 0.03684 -0.01230 0.01277 -0.00555 H1WA 2 0.614674 0.696379 0.508518 11.00000 -1.50000 H1WB 2 0.576364 0.756460 0.460470 11.00000 -1.50000 AFIX 0 C13 1 0.381262 0.422924 0.837165 11.00000 0.01390 0.02074 = 0.02037 0.00206 0.00211 -0.00047 C9 1 0.382540 0.452364 0.701279 11.00000 0.01543 0.01842 = 0.01750 -0.00139 0.00236 -0.00135 C15 1 0.222943 0.630672 0.704652 11.00000 0.01571 0.01799 = 0.02814 -0.00063 0.00090 0.00013 C6 1 0.375505 0.836755 0.620944 11.00000 0.01475 0.02352 = 0.02972 0.00783 0.00042 0.00101 C8 1 0.387854 0.511850 0.637437 11.00000 0.02185 0.01771 = 0.01561 -0.00346 0.00202 -0.00395 AFIX 23 H8A 2 0.415696 0.488775 0.592870 11.00000 -1.20000 H8B 2 0.319842 0.528796 0.613787 11.00000 -1.20000 AFIX 0 C12 1 0.368704 0.347192 0.818865 11.00000 0.02271 0.01931 = 0.02840 0.00532 0.00475 -0.00175 AFIX 43 H12 2 0.363874 0.311578 0.860403 11.00000 -1.20000 AFIX 0 C2 1 0.386331 0.811277 0.759682 11.00000 0.01268 0.01821 = 0.02508 -0.00111 -0.00138 0.00125 C3 1 0.376837 0.887206 0.775645 11.00000 0.02444 0.02097 = 0.03575 -0.00446 0.00302 0.00228 AFIX 43 H3 2 0.378172 0.904037 0.829889 11.00000 -1.20000 AFIX 0 C1 1 0.391817 0.753148 0.826392 11.00000 0.02093 0.01818 = 0.02102 -0.00203 0.00185 0.00589 AFIX 23 H1A 2 0.421770 0.776790 0.879185 11.00000 -1.20000 H1B 2 0.323679 0.737781 0.829712 11.00000 -1.20000 AFIX 0 C14 1 0.390667 0.450471 0.924037 11.00000 0.02590 0.02115 = 0.02032 0.00332 0.00353 -0.00262 AFIX 23 H14A 2 0.334758 0.430531 0.946901 11.00000 -1.20000 H14B 2 0.452674 0.430535 0.957471 11.00000 -1.20000 AFIX 0 C10 1 0.370058 0.377310 0.679830 11.00000 0.02635 0.02140 = 0.02387 -0.00522 0.00596 -0.00379 AFIX 43 H10 2 0.366123 0.362158 0.624689 11.00000 -1.20000 AFIX 0 PART 1 O7 5 0.220738 0.565991 0.969459 10.55000 0.04885 0.04469 = 0.06749 -0.00162 0.02483 0.01003 PART 0 C5 1 0.364558 0.913022 0.634022 11.00000 0.02492 0.02249 = 0.04071 0.01239 0.00020 0.00264 AFIX 43 H5 2 0.356565 0.947394 0.589569 11.00000 -1.20000 AFIX 0 C11 1 0.363332 0.324356 0.739419 11.00000 0.02713 0.01545 = 0.03781 -0.00226 0.00671 -0.00225 AFIX 43 H11 2 0.355051 0.272533 0.725476 11.00000 -1.20000 AFIX 0 C4 1 0.365348 0.938539 0.711668 11.00000 0.02876 0.01603 = 0.05153 0.00088 0.00527 0.00242 AFIX 43 H4A 2 0.358116 0.990754 0.721607 11.00000 -1.20000 AFIX 0 C16 1 0.111711 0.628151 0.685540 11.00000 0.01705 0.03888 = 0.04255 0.01068 0.00064 -0.00123 AFIX 137 H16A 2 0.089717 0.583833 0.651809 11.00000 -1.50000 H16B 2 0.086133 0.673871 0.655794 11.00000 -1.50000 H16C 2 0.086822 0.625107 0.736568 11.00000 -1.50000 AFIX 0 PART 1 O11 5 0.244245 0.681407 0.937328 10.55000 0.05128 0.04164 = 0.05417 -0.01020 0.01050 -0.00100 PART 0 C7 1 0.372694 0.806705 0.535735 11.00000 0.03700 0.02928 = 0.02660 0.01177 0.00290 0.00521 AFIX 23 H7A 2 0.306863 0.817365 0.501681 11.00000 -1.20000 H7B 2 0.422654 0.833743 0.511346 11.00000 -1.20000 AFIX 0 PART 1 N3 4 0.189382 0.629541 0.945760 10.55000 0.02771 0.04168 = 0.04703 -0.01229 0.00127 0.00058 O9 5 0.098709 0.638991 0.932033 10.55000 0.02860 0.09025 = 0.12931 -0.02639 -0.00936 0.00745 PART 0 PART 2 O6 5 0.221831 0.552942 0.991654 10.45000 0.05017 0.05132 = 0.05013 -0.01079 -0.00525 0.02392 N4 4 0.179968 0.613895 0.977094 10.45000 0.04796 0.04817 = 0.04534 -0.02208 -0.00514 0.00375 O8 5 0.094262 0.624422 0.986066 10.45000 0.03983 0.07504 = 0.11107 -0.03430 0.00366 0.02252 O10 5 0.226957 0.667537 0.955516 10.45000 0.10518 0.07664 = 0.10620 0.00427 0.01758 -0.00763 PART 0 PART -1 AFIX 6 O2W 5 0.039070 0.512834 1.041482 10.50000 0.12638 0.12555 = 0.08321 -0.01512 0.04750 -0.03930 H2WA 2 -0.000298 0.478989 1.014967 10.50000 -1.50000 H2WB 2 0.066176 0.538523 1.007274 10.50000 -1.50000 AFIX 0 PART 0 H4 2 0.341131 0.543659 0.945661 11.00000 0.05921 H2 2 0.442788 0.723697 0.521471 11.00000 0.02700 HKLF 4 REM mo_2017524-2017062208_0m_a.res in C2/c REM R1 = 0.0282 for 3891 Fo > 4sig(Fo) and 0.0361 for all 4599 data REM 340 parameters refined using 57 restraints END WGHT 0.0381 1.4176 REM Highest difference peak 0.423, deepest hole -0.471, 1-sigma level 0.087 Q1 1 0.4056 0.7379 0.6569 11.00000 0.05 0.42 Q2 1 0.3263 0.6405 0.6527 11.00000 0.05 0.40 Q3 1 0.2656 0.6029 0.9909 11.00000 0.05 0.38 Q4 1 0.4958 0.6753 0.8579 11.00000 0.05 0.35 Q5 1 0.4790 0.6232 0.8133 11.00000 0.05 0.35 Q6 1 0.4754 0.5736 0.7149 11.00000 0.05 0.35 Q7 1 0.3770 0.8730 0.6334 11.00000 0.05 0.34 Q8 1 0.4216 0.5452 0.6529 11.00000 0.05 0.33 Q9 1 0.4986 0.5486 0.6690 11.00000 0.05 0.32 Q10 1 0.3670 0.3520 0.7059 11.00000 0.05 0.32 Q11 1 0.3831 0.3861 0.8274 11.00000 0.05 0.32 Q12 1 0.2560 0.6409 0.6331 11.00000 0.05 0.31 Q13 1 0.3154 0.6033 0.7733 11.00000 0.05 0.31 Q14 1 0.1633 0.5295 1.0324 11.00000 0.05 0.31 Q15 1 0.4972 0.7118 0.5107 11.00000 0.05 0.30 Q16 1 0.3848 0.4604 0.7378 11.00000 0.05 0.30 Q17 1 0.2741 0.6615 0.9086 11.00000 0.05 0.30 Q18 1 0.1649 0.6376 0.6970 11.00000 0.05 0.30 Q19 1 0.2777 0.6393 0.7797 11.00000 0.05 0.30 Q20 1 0.2448 0.6315 0.6575 11.00000 0.05 0.29 REM The information below was added by Olex2. REM REM R1 = 0.0282 for 3891 Fo > 4sig(Fo) and 0.0361 for all 18143 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.42, deepest hole -0.47 REM Mean Shift 0, Max Shift 0.003. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0361 REM R1_gt = 0.0282 REM wR_ref = 0.0764 REM GOOF = 1.050 REM Shift_max = 0.003 REM Shift_mean = 0 REM Reflections_all = 18143 REM Reflections_gt = 3891 REM Parameters = n/a REM Hole = -0.47 REM Peak = 0.42 REM Flack = n/a ; _cod_data_source_file c8nj06263c2.cif _cod_data_source_block mo_2017524-2017062208_0m _cod_original_cell_volume 4003.2(13) _cod_database_code 7058201 _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_max 0.795 _shelx_estimated_absorpt_t_min 0.579 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H,H) groups 2. Restrained distances O4-H4 0.86 with sigma of 0.02 O6-N4 \\sim O8-N4 \\sim O10-N4 with sigma of 0.02 O7-N3 \\sim O9-N3 \\sim O11-N3 with sigma of 0.02 O8-O6 \\sim O6-O10 with sigma of 0.02 O7-O9 \\sim O9-O11 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(O9) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O11) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 Uanis(O7) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(O11) \\sim Ueq: with sigma of 0.006 and sigma for terminal atoms of 0.012 4. Others Fixed Sof: O7(0.55) O11(0.55) N3(0.55) O9(0.55) O6(0.45) N4(0.45) O8(0.45) O10(0.45) O2W(0.5) H2WA(0.5) H2WB(0.5) 5.a Free rotating group: O1W(H1WA,H1WB), O2W(H2WA,H2WB) 5.b Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C1(H1A,H1B), C14(H14A,H14B), C7(H7A,H7B) 5.c Aromatic/amide H refined with riding coordinates: C12(H12), C3(H3), C10(H10), C5(H5), C11(H11), C4(H4A) 5.d Idealised Me refined as rotating group: C16(H16A,H16B,H16C) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 Cu2 Cu 0.40846(2) 0.58261(2) 0.80621(2) 0.01508(8) Uani 1 1 d . . . . . Cu1 Cu 0.40697(2) 0.67983(2) 0.66423(2) 0.01570(8) Uani 1 1 d . . . . . O1 O 0.44668(10) 0.68796(8) 0.81576(9) 0.0169(3) Uani 1 1 d . . . . . O3 O 0.44538(10) 0.57541(8) 0.66710(9) 0.0161(3) Uani 1 1 d . . . . . O5 O 0.26557(11) 0.60174(9) 0.77084(9) 0.0213(3) Uani 1 1 d . . . . . O4 O 0.39125(12) 0.53021(9) 0.92945(9) 0.0243(3) Uani 1 1 d D . . . . O0AA O 0.26450(11) 0.66106(9) 0.65202(9) 0.0236(3) Uani 1 1 d . . . . . O2 O 0.39115(13) 0.72862(9) 0.53387(10) 0.0265(4) Uani 1 1 d . . . . . N2 N 0.38820(12) 0.47413(10) 0.77946(10) 0.0165(3) Uani 1 1 d . . . . . N1 N 0.38608(12) 0.78742(10) 0.68309(11) 0.0184(4) Uani 1 1 d . . . . . O1W O 0.56073(14) 0.71241(13) 0.47704(12) 0.0434(5) Uani 1 1 d . . . . . H1WA H 0.6147 0.6964 0.5085 0.065 Uiso 1 1 d G . . . . H1WB H 0.5764 0.7565 0.4605 0.065 Uiso 1 1 d G . . . . C13 C 0.38126(15) 0.42292(12) 0.83716(13) 0.0185(4) Uani 1 1 d . . . . . C9 C 0.38254(14) 0.45236(12) 0.70128(12) 0.0172(4) Uani 1 1 d . . . . . C15 C 0.22294(15) 0.63067(12) 0.70465(14) 0.0211(4) Uani 1 1 d . . . . . C6 C 0.37551(15) 0.83675(13) 0.62094(14) 0.0232(5) Uani 1 1 d . . . . . C8 C 0.38785(15) 0.51185(12) 0.63744(12) 0.0186(4) Uani 1 1 d . . . . . H8A H 0.4157 0.4888 0.5929 0.022 Uiso 1 1 calc R . . . . H8B H 0.3198 0.5288 0.6138 0.022 Uiso 1 1 calc R . . . . C12 C 0.36870(16) 0.34719(13) 0.81887(14) 0.0235(5) Uani 1 1 d . . . . . H12 H 0.3639 0.3116 0.8604 0.028 Uiso 1 1 calc R . . . . C2 C 0.38633(15) 0.81128(12) 0.75968(13) 0.0193(4) Uani 1 1 d . . . . . C3 C 0.37684(17) 0.88721(13) 0.77565(15) 0.0274(5) Uani 1 1 d . . . . . H3 H 0.3782 0.9040 0.8299 0.033 Uiso 1 1 calc R . . . . C1 C 0.39182(16) 0.75315(12) 0.82639(13) 0.0204(4) Uani 1 1 d . . . . . H1A H 0.4218 0.7768 0.8792 0.024 Uiso 1 1 calc R . . . . H1B H 0.3237 0.7378 0.8297 0.024 Uiso 1 1 calc R . . . . C14 C 0.39067(17) 0.45047(13) 0.92404(13) 0.0226(5) Uani 1 1 d . . . . . H14A H 0.3348 0.4305 0.9469 0.027 Uiso 1 1 calc R . . . . H14B H 0.4527 0.4305 0.9575 0.027 Uiso 1 1 calc R . . . . C10 C 0.37006(16) 0.37731(13) 0.67983(14) 0.0237(5) Uani 1 1 d . . . . . H10 H 0.3661 0.3622 0.6247 0.028 Uiso 1 1 calc R . . . . O7 O 0.2207(9) 0.5660(6) 0.9695(7) 0.052(2) Uani 0.55 1 d D U P A 1 C5 C 0.36456(17) 0.91302(13) 0.63402(16) 0.0302(5) Uani 1 1 d . . . . . H5 H 0.3566 0.9474 0.5896 0.036 Uiso 1 1 calc R . . . . C11 C 0.36333(17) 0.32436(13) 0.73942(15) 0.0267(5) Uani 1 1 d . . . . . H11 H 0.3551 0.2725 0.7255 0.032 Uiso 1 1 calc R . . . . C4 C 0.36535(18) 0.93854(14) 0.71167(17) 0.0325(6) Uani 1 1 d . . . . . H4A H 0.3581 0.9908 0.7216 0.039 Uiso 1 1 calc R . . . . C16 C 0.11171(16) 0.62815(15) 0.68554(16) 0.0335(6) Uani 1 1 d . . . . . H16A H 0.0897 0.5838 0.6518 0.050 Uiso 1 1 calc GR . . . . H16B H 0.0861 0.6739 0.6558 0.050 Uiso 1 1 calc GR . . . . H16C H 0.0868 0.6251 0.7366 0.050 Uiso 1 1 calc GR . . . . O11 O 0.2442(6) 0.6814(5) 0.9373(5) 0.0490(15) Uani 0.55 1 d D U P A 1 C7 C 0.3727(2) 0.80670(14) 0.53574(15) 0.0314(5) Uani 1 1 d . . . . . H7A H 0.3069 0.8174 0.5017 0.038 Uiso 1 1 calc R . . . . H7B H 0.4227 0.8337 0.5113 0.038 Uiso 1 1 calc R . . . . N3 N 0.1894(4) 0.6295(4) 0.9458(4) 0.0396(15) Uani 0.55 1 d D U P A 1 O9 O 0.0987(4) 0.6390(4) 0.9320(4) 0.086(2) Uani 0.55 1 d D U P A 1 O6 O 0.2218(11) 0.5529(8) 0.9917(8) 0.053(3) Uani 0.45 1 d D U P B 2 N4 N 0.1800(6) 0.6139(5) 0.9771(5) 0.049(2) Uani 0.45 1 d D U P B 2 O8 O 0.0943(5) 0.6244(4) 0.9861(5) 0.077(2) Uani 0.45 1 d D U P B 2 O10 O 0.2270(11) 0.6675(8) 0.9555(9) 0.096(5) Uani 0.45 1 d D U P B 2 O2W O 0.0391(6) 0.5128(5) 1.0415(4) 0.108(2) Uani 0.5 1 d . . P C -1 H2WA H -0.0003 0.4790 1.0150 0.162 Uiso 0.5 1 d G . P C -1 H2WB H 0.0662 0.5385 1.0073 0.162 Uiso 0.5 1 d G . P C -1 H4 H 0.3411(18) 0.5437(18) 0.946(2) 0.059(10) Uiso 1 1 d D . . . . H2 H 0.443(2) 0.7237(15) 0.5215(16) 0.027(7) 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 Cu2 0.01525(13) 0.01452(14) 0.01442(13) -0.00013(9) 0.00035(9) -0.00040(9) Cu1 0.01439(13) 0.01506(14) 0.01631(13) 0.00183(10) -0.00028(9) -0.00021(9) O1 0.0148(7) 0.0142(7) 0.0205(7) -0.0023(6) 0.0008(6) 0.0018(6) O3 0.0150(7) 0.0140(7) 0.0180(7) -0.0014(6) 0.0001(5) -0.0013(6) O5 0.0176(7) 0.0230(8) 0.0226(8) 0.0007(7) 0.0024(6) -0.0001(6) O4 0.0318(9) 0.0227(8) 0.0186(7) -0.0011(7) 0.0051(7) -0.0019(7) O0AA 0.0156(7) 0.0262(8) 0.0269(8) 0.0045(7) -0.0014(6) -0.0018(6) O2 0.0284(9) 0.0272(9) 0.0230(8) 0.0038(7) 0.0030(7) -0.0011(7) N2 0.0145(8) 0.0178(9) 0.0163(8) -0.0003(7) 0.0010(6) -0.0008(7) N1 0.0124(8) 0.0172(9) 0.0234(9) 0.0015(8) -0.0022(7) 0.0010(7) O1W 0.0442(11) 0.0511(13) 0.0368(11) -0.0123(10) 0.0128(9) -0.0056(10) C13 0.0139(9) 0.0207(11) 0.0204(10) 0.0021(9) 0.0021(8) -0.0005(8) C9 0.0154(9) 0.0184(11) 0.0175(10) -0.0014(8) 0.0024(8) -0.0014(8) C15 0.0157(10) 0.0180(11) 0.0281(11) -0.0006(9) 0.0009(8) 0.0001(8) C6 0.0147(10) 0.0235(12) 0.0297(12) 0.0078(10) 0.0004(9) 0.0010(9) C8 0.0219(10) 0.0177(11) 0.0156(10) -0.0035(9) 0.0020(8) -0.0040(8) C12 0.0227(11) 0.0193(11) 0.0284(12) 0.0053(9) 0.0048(9) -0.0018(9) C2 0.0127(9) 0.0182(11) 0.0251(11) -0.0011(9) -0.0014(8) 0.0012(8) C3 0.0244(11) 0.0210(12) 0.0358(13) -0.0045(10) 0.0030(10) 0.0023(9) C1 0.0209(10) 0.0182(11) 0.0210(10) -0.0020(9) 0.0018(8) 0.0059(9) C14 0.0259(11) 0.0212(11) 0.0203(10) 0.0033(9) 0.0035(9) -0.0026(9) C10 0.0263(11) 0.0214(12) 0.0239(11) -0.0052(9) 0.0060(9) -0.0038(9) O7 0.049(4) 0.045(4) 0.067(6) -0.002(3) 0.025(4) 0.010(3) C5 0.0249(12) 0.0225(13) 0.0407(14) 0.0124(11) 0.0002(10) 0.0026(10) C11 0.0271(12) 0.0154(11) 0.0378(13) -0.0023(10) 0.0067(10) -0.0023(9) C4 0.0288(12) 0.0160(11) 0.0515(16) 0.0009(11) 0.0053(11) 0.0024(10) C16 0.0170(11) 0.0389(15) 0.0426(15) 0.0107(12) 0.0006(10) -0.0012(10) O11 0.051(3) 0.042(3) 0.054(3) -0.010(3) 0.010(3) -0.001(2) C7 0.0370(14) 0.0293(13) 0.0266(12) 0.0118(10) 0.0029(10) 0.0052(11) N3 0.028(2) 0.042(3) 0.047(3) -0.012(3) 0.001(2) 0.001(2) O9 0.029(2) 0.090(4) 0.129(5) -0.026(4) -0.009(3) 0.007(2) O6 0.050(5) 0.051(6) 0.050(6) -0.011(4) -0.005(4) 0.024(4) N4 0.048(4) 0.048(4) 0.045(4) -0.022(3) -0.005(3) 0.004(3) O8 0.040(3) 0.075(5) 0.111(5) -0.034(5) 0.004(4) 0.023(3) O10 0.105(9) 0.077(7) 0.106(9) 0.004(6) 0.018(6) -0.008(6) O2W 0.126(6) 0.126(7) 0.083(4) -0.015(4) 0.048(4) -0.039(5) 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' 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 O1 Cu2 O3 78.22(6) . 2_656 O1 Cu2 O5 95.62(6) . . O1 Cu2 O4 112.84(6) . . O1 Cu2 N2 167.84(6) . . O3 Cu2 O4 92.94(6) 2_656 . O3 Cu2 N2 94.60(6) 2_656 . O5 Cu2 O3 172.31(6) . 2_656 O5 Cu2 O4 93.72(6) . . O5 Cu2 N2 90.66(7) . . N2 Cu2 O4 77.02(6) . . O1 Cu1 O2 92.09(6) 2_656 . O3 Cu1 O1 78.47(6) . 2_656 O3 Cu1 O0AA 95.97(6) . . O3 Cu1 O2 111.02(6) . . O3 Cu1 N1 168.30(7) . . O0AA Cu1 O1 173.35(6) . 2_656 O0AA Cu1 O2 93.33(6) . . O0AA Cu1 N1 90.37(7) . . N1 Cu1 O1 94.50(6) . 2_656 N1 Cu1 O2 78.30(7) . . Cu2 O1 Cu1 101.22(6) . 2_656 C1 O1 Cu2 131.00(13) . . C1 O1 Cu1 126.17(13) . 2_656 Cu1 O3 Cu2 101.90(6) . 2_656 C8 O3 Cu2 127.39(12) . 2_656 C8 O3 Cu1 128.87(13) . . C15 O5 Cu2 127.00(14) . . Cu2 O4 H4 114(2) . . C14 O4 Cu2 110.19(12) . . C14 O4 H4 108(2) . . C15 O0AA Cu1 125.64(14) . . Cu1 O2 H2 106(2) . . C7 O2 Cu1 109.35(14) . . C7 O2 H2 107(2) . . C13 N2 Cu2 121.52(14) . . C13 N2 C9 120.14(18) . . C9 N2 Cu2 118.34(14) . . C6 N1 Cu1 120.44(15) . . C6 N1 C2 120.54(19) . . C2 N1 Cu1 118.98(15) . . H1WA O1W H1WB 104.5 . . N2 C13 C12 121.6(2) . . N2 C13 C14 117.70(18) . . C12 C13 C14 120.68(19) . . N2 C9 C8 118.71(18) . . N2 C9 C10 120.5(2) . . C10 C9 C8 120.76(18) . . O5 C15 O0AA 126.18(19) . . O5 C15 C16 117.15(19) . . O0AA C15 C16 116.66(19) . . N1 C6 C5 121.0(2) . . N1 C6 C7 118.4(2) . . C5 C6 C7 120.6(2) . . O3 C8 C9 114.35(17) . . O3 C8 H8A 108.7 . . O3 C8 H8B 108.7 . . C9 C8 H8A 108.7 . . C9 C8 H8B 108.7 . . H8A C8 H8B 107.6 . . C13 C12 H12 120.6 . . C11 C12 C13 118.7(2) . . C11 C12 H12 120.6 . . N1 C2 C3 120.4(2) . . N1 C2 C1 118.44(19) . . C3 C2 C1 121.1(2) . . C2 C3 H3 120.3 . . C2 C3 C4 119.4(2) . . C4 C3 H3 120.3 . . O1 C1 C2 114.71(17) . . O1 C1 H1A 108.6 . . O1 C1 H1B 108.6 . . C2 C1 H1A 108.6 . . C2 C1 H1B 108.6 . . H1A C1 H1B 107.6 . . O4 C14 C13 112.47(17) . . O4 C14 H14A 109.1 . . O4 C14 H14B 109.1 . . C13 C14 H14A 109.1 . . C13 C14 H14B 109.1 . . H14A C14 H14B 107.8 . . C9 C10 H10 120.3 . . C9 C10 C11 119.4(2) . . C11 C10 H10 120.3 . . C6 C5 H5 120.3 . . C4 C5 C6 119.4(2) . . C4 C5 H5 120.3 . . C12 C11 C10 119.6(2) . . C12 C11 H11 120.2 . . C10 C11 H11 120.2 . . C3 C4 H4A 120.4 . . C5 C4 C3 119.3(2) . . C5 C4 H4A 120.4 . . C15 C16 H16A 109.5 . . C15 C16 H16B 109.5 . . C15 C16 H16C 109.5 . . H16A C16 H16B 109.5 . . H16A C16 H16C 109.5 . . H16B C16 H16C 109.5 . . O2 C7 C6 113.32(19) . . O2 C7 H7A 108.9 . . O2 C7 H7B 108.9 . . C6 C7 H7A 108.9 . . C6 C7 H7B 108.9 . . H7A C7 H7B 107.7 . . O11 N3 O7 122.5(8) . . O11 N3 O9 120.3(7) . . O9 N3 O7 117.2(8) . . O6 N4 O8 122.2(10) . . O6 N4 O10 118.7(11) . . O8 N4 O10 119.0(11) . . H2WA O2W H2WB 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cu2 O1 1.9404(15) . Cu2 O3 1.9806(14) 2_656 Cu2 O5 1.9717(15) . Cu2 O4 2.3113(16) . Cu2 N2 1.9835(18) . Cu1 O1 1.9845(15) 2_656 Cu1 O3 1.9253(14) . Cu1 O0AA 1.9627(15) . Cu1 O2 2.3117(16) . Cu1 N1 1.9655(18) . O1 Cu1 1.9845(15) 2_656 O1 C1 1.412(2) . O3 Cu2 1.9805(14) 2_656 O3 C8 1.411(2) . O5 C15 1.255(3) . O4 C14 1.418(3) . O4 H4 0.825(18) . O0AA C15 1.260(3) . O2 C7 1.410(3) . O2 H2 0.78(3) . N2 C13 1.341(3) . N2 C9 1.348(3) . N1 C6 1.343(3) . N1 C2 1.346(3) . O1W H1WA 0.8699 . O1W H1WB 0.8702 . C13 C12 1.382(3) . C13 C14 1.511(3) . C9 C8 1.512(3) . C9 C10 1.381(3) . C15 C16 1.504(3) . C6 C5 1.384(3) . C6 C7 1.512(3) . C8 H8A 0.9900 . C8 H8B 0.9900 . C12 H12 0.9500 . C12 C11 1.374(3) . C2 C3 1.385(3) . C2 C1 1.509(3) . C3 H3 0.9500 . C3 C4 1.389(3) . C1 H1A 0.9900 . C1 H1B 0.9900 . C14 H14A 0.9900 . C14 H14B 0.9900 . C10 H10 0.9500 . C10 C11 1.384(3) . O7 N3 1.244(10) . C5 H5 0.9500 . C5 C4 1.371(4) . C11 H11 0.9500 . C4 H4A 0.9500 . C16 H16A 0.9800 . C16 H16B 0.9800 . C16 H16C 0.9800 . O11 N3 1.217(10) . C7 H7A 0.9900 . C7 H7B 0.9900 . N3 O9 1.237(7) . O6 N4 1.228(12) . N4 O8 1.234(9) . N4 O10 1.244(11) . O2W H2WA 0.8700 . O2W H2WB 0.8701 .