#------------------------------------------------------------------------------ #$Date: 2020-08-22 05:20:15 +0300 (Sat, 22 Aug 2020) $ #$Revision: 255579 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705251.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_7705251 loop_ _publ_author_name 'Shen, Guodong' 'Wang, Zeyou' 'Huang, Xianqiang' 'Gong, Shuwen' 'Zhang, Jiangong' 'Tang, Zhenfei' 'Sun, Manman' 'Lv, Xin' _publ_section_title ; Bonded- and Discreted- Linqvist Hexatungstate-Based Copper hybrids as Heterogeneous Catalysts for One-pot Synthesis of 2-Phenylquinoxalines via 2-Haloanilines with Vinyl Azides or 3-Phenyl-2H-azirines ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D0DT02625E _journal_year 2020 _chemical_formula_sum 'C48 H46 Cu4 N8 O29 W6' _chemical_formula_weight 2556.19 _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 _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-06-09 deposited with the CCDC. 2020-08-19 downloaded from the CCDC. ; _cell_angle_alpha 108.267(3) _cell_angle_beta 101.159(2) _cell_angle_gamma 106.443(3) _cell_formula_units_Z 1 _cell_length_a 10.6500(9) _cell_length_b 12.1479(11) _cell_length_c 13.1931(12) _cell_measurement_reflns_used 1024 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 28.193 _cell_measurement_theta_min 3.3095 _cell_volume 1478.0(2) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_unetI/netI 0.0440 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.985 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 7550 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.985 _diffrn_reflns_theta_full 25.015 _diffrn_reflns_theta_max 25.015 _diffrn_reflns_theta_min 2.258 _exptl_absorpt_coefficient_mu 13.126 _exptl_absorpt_correction_T_max 0.2138 _exptl_absorpt_correction_T_min 0.1603 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour green _exptl_crystal_density_diffrn 2.872 _exptl_crystal_description block _exptl_crystal_F_000 1182 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.170 _refine_diff_density_max 4.175 _refine_diff_density_min -4.097 _refine_diff_density_rms 0.433 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 430 _refine_ls_number_reflns 5156 _refine_ls_number_restraints 444 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0585 _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^)+(0.1118P)^2^+61.0228P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1874 _refine_ls_wR_factor_ref 0.1953 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4232 _reflns_number_total 5156 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02625e2.cif _cod_data_source_block 161026c _cod_database_code 7705251 _shelx_shelxl_version_number 2018/3 _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_min 0.160 _shelx_estimated_absorpt_t_max 0.214 _shelx_res_file ; TITL 161026c in P-1 161026c.res created by SHELXL-2018/3 at 11:18:10 on 28-May-2019 CELL 0.71073 10.6500 12.1479 13.1931 108.267 101.159 106.443 ZERR 1 0.0009 0.0011 0.0012 0.003 0.002 0.003 LATT 1 SFAC C H N O Cu W UNIT 48 46 8 29 4 6 OMIT -1.00 50.04 L.S. 8 ACTA BOND $H FMAP 2 PLAN 20 size 0.22 0.19 0.17 simu 0.01 0.02 3.8 $o $w $cu isor 0.001 o2 o7 o8 c21 isor 0.01 o6 c7 c14 c3 c22 delu 0.002 0.001 w1 o8 w3 o2 o8 htab FREE Cu1 Cu2 TEMP 25 WGHT 0.111800 61.022800 FVAR 0.12697 W1 6 0.351470 0.451535 0.328296 11.00000 0.03028 0.03273 = 0.02950 0.01610 0.00789 0.01197 W2 6 0.362281 0.588467 0.585691 11.00000 0.01950 0.02144 = 0.02320 0.01337 0.01361 0.01248 W3 6 0.622630 0.689112 0.498636 11.00000 0.02882 0.02623 = 0.03235 0.01700 0.01293 0.01012 CU1 5 0.173479 0.092116 0.198554 11.00000 0.01087 0.01449 = 0.01854 0.01490 0.00687 0.00729 CU2 5 0.134573 0.222104 0.050993 11.00000 0.00973 0.01515 = 0.01207 0.01186 0.00433 0.00618 N1 3 0.309107 0.015667 0.245060 11.00000 0.01432 0.01235 = 0.01559 0.01020 0.00417 0.00381 N2 3 0.065171 -0.003249 0.275358 11.00000 0.01228 0.01530 = 0.01859 0.01129 0.00958 0.00972 N3 3 0.235528 0.291803 -0.044590 11.00000 0.00876 0.01396 = 0.01244 0.00375 0.00537 0.00659 N4 3 -0.011614 0.272798 -0.022475 11.00000 0.01718 0.00933 = 0.00857 0.00654 0.00405 0.00393 O1 4 0.239070 0.409534 0.199949 11.00000 0.01792 0.01900 = 0.02091 0.01315 0.00659 0.01005 O2 4 0.718331 0.702891 0.642389 11.00000 0.02517 0.02427 = 0.02651 0.01005 0.01038 0.00952 O3 4 0.260848 0.523094 0.428038 11.00000 0.01350 0.01947 = 0.01918 0.01325 0.01067 0.01260 O4 4 0.260533 0.651319 0.649994 11.00000 0.02068 0.01835 = 0.02266 0.01272 0.01651 0.01328 O5 4 0.510295 0.615439 0.711946 11.00000 0.01377 0.01824 = 0.01783 0.01154 0.01248 0.01210 O6 4 0.500000 0.500000 0.500000 10.50000 0.01709 0.01691 = 0.01870 0.01242 0.01250 0.01128 O7 4 0.290018 0.415489 0.570928 11.00000 0.01407 0.01470 = 0.01443 0.00605 0.00547 0.00553 O8 4 0.471620 0.610512 0.356478 11.00000 0.02776 0.02780 = 0.02811 0.01088 0.01032 0.01165 O9 4 0.480931 0.722541 0.565001 11.00000 0.01557 0.01692 = 0.01987 0.01288 0.01313 0.01396 O10 4 0.703990 0.827063 0.494095 11.00000 0.01912 0.01574 = 0.02368 0.01282 0.01053 0.00669 O11 4 0.268290 0.155994 0.105301 11.00000 0.01456 0.02009 = 0.01996 0.01273 0.01010 0.01022 AFIX 3 H11B 2 0.346890 0.212814 0.143411 11.00000 -1.20000 AFIX 0 O12 4 0.029971 0.141726 0.130586 11.00000 0.01367 0.02091 = 0.02059 0.01713 0.00641 0.00797 O13 4 0.405995 0.792186 0.907054 11.00000 0.03064 0.03941 = 0.03033 0.00929 0.01163 0.00407 AFIX 3 H13C 2 0.372165 0.746496 0.837324 11.00000 -1.20000 H13D 2 0.374855 0.850636 0.920014 11.00000 -1.20000 AFIX 0 O14 4 0.279932 -0.023179 0.917263 11.00000 0.11809 0.03656 = 0.03580 0.01011 0.01860 0.03692 AFIX 3 H14C 2 0.294402 0.038241 0.977123 11.00000 -1.20000 H14D 2 0.194302 -0.066979 0.892473 11.00000 -1.20000 AFIX 0 O15 4 0.978727 0.295253 0.320508 11.00000 0.02460 0.05688 = 0.07175 0.00154 0.01912 0.02105 AFIX 3 H15C 2 1.062837 0.314793 0.355458 11.00000 -1.20000 H15D 2 0.962107 0.244213 0.253988 11.00000 -1.20000 AFIX 0 C1 1 0.429930 0.027872 0.226895 11.00000 0.01491 0.02061 = 0.03328 0.01751 0.01171 0.00840 AFIX 43 H1 2 0.458275 0.072566 0.184346 11.00000 -1.20000 AFIX 0 C2 1 0.515431 -0.026469 0.271684 11.00000 0.00987 0.03904 = 0.04020 0.03076 0.01166 0.01385 AFIX 43 H2 2 0.598946 -0.017547 0.257072 11.00000 -1.20000 AFIX 0 C3 1 0.479935 -0.090937 0.335006 11.00000 0.02204 0.03177 = 0.03258 0.01597 0.00108 0.01658 AFIX 43 H3 2 0.538987 -0.123907 0.365634 11.00000 -1.20000 AFIX 0 C4 1 0.347698 -0.107601 0.354173 11.00000 0.01605 0.02313 = 0.02341 0.01757 0.00627 0.01117 C5 1 0.269351 -0.050169 0.306575 11.00000 0.00833 0.00872 = 0.00692 -0.00087 -0.00083 -0.00236 C6 1 0.134615 -0.062734 0.320563 11.00000 0.00827 0.00972 = 0.01359 0.00331 0.00524 0.00004 C7 1 0.083506 -0.133522 0.381614 11.00000 0.01827 0.00618 = 0.01664 0.00781 0.00442 0.00266 C8 1 0.170867 -0.186502 0.431374 11.00000 0.02838 0.02570 = 0.02228 0.01878 0.00379 0.00990 AFIX 43 H8 2 0.141266 -0.228776 0.475315 11.00000 -1.20000 AFIX 0 C9 1 0.297229 -0.176039 0.415418 11.00000 0.02635 0.02659 = 0.02418 0.01964 0.00204 0.00833 AFIX 43 H9 2 0.349420 -0.214638 0.445479 11.00000 -1.20000 AFIX 0 C10 1 -0.049184 -0.142669 0.391576 11.00000 0.02164 0.01882 = 0.01203 0.00210 0.00707 0.00188 AFIX 43 H10 2 -0.088603 -0.189218 0.429214 11.00000 -1.20000 AFIX 0 C11 1 -0.118857 -0.081584 0.344677 11.00000 0.01621 0.02244 = 0.02716 0.01591 0.01009 0.01171 AFIX 43 H11 2 -0.204985 -0.085810 0.352104 11.00000 -1.20000 AFIX 0 C12 1 -0.060622 -0.012652 0.285460 11.00000 0.02270 0.01899 = 0.02424 0.01129 0.01610 0.01277 AFIX 43 H12 2 -0.109649 0.026635 0.253123 11.00000 -1.20000 AFIX 0 C13 1 0.359162 0.298644 -0.056389 11.00000 0.01256 0.03907 = 0.02311 0.02132 0.01045 0.01070 AFIX 43 H13 2 0.409747 0.263457 -0.019809 11.00000 -1.20000 AFIX 0 C14 1 0.414752 0.357638 -0.122650 11.00000 0.01208 0.02842 = 0.02958 0.01557 0.01137 0.00860 AFIX 43 H14 2 0.500126 0.358741 -0.130077 11.00000 -1.20000 AFIX 0 C15 1 0.346696 0.413189 -0.176207 11.00000 0.01801 0.02916 = 0.02160 0.01449 0.01600 0.00863 AFIX 43 H15 2 0.385117 0.453953 -0.218215 11.00000 -1.20000 AFIX 0 C16 1 0.213751 0.406410 -0.165346 11.00000 0.01004 0.01481 = 0.00698 0.00714 0.00166 0.00313 C17 1 0.163802 0.343933 -0.100207 11.00000 0.01508 0.00818 = 0.00431 0.00107 0.00170 0.00246 C18 1 0.028049 0.332748 -0.088630 11.00000 0.00553 0.01350 = 0.00192 0.00176 0.00074 0.00273 C19 1 -0.050645 0.386871 -0.141799 11.00000 0.01485 0.01036 = 0.01208 0.00419 0.00586 0.00544 C20 1 0.002309 0.449250 -0.208779 11.00000 0.02481 0.01698 = 0.01230 0.01213 0.00654 0.00833 AFIX 43 H20 2 -0.050058 0.483613 -0.244813 11.00000 -1.20000 AFIX 0 C21 1 0.128864 0.458717 -0.220198 11.00000 0.01671 0.01651 = 0.01642 0.00694 0.00496 0.00588 AFIX 43 H21 2 0.161607 0.499612 -0.264126 11.00000 -1.20000 AFIX 0 C22 1 -0.181521 0.372289 -0.125872 11.00000 0.01280 0.02189 = 0.02443 0.00697 0.00224 0.01266 AFIX 43 H22 2 -0.239866 0.402764 -0.161052 11.00000 -1.20000 AFIX 0 C23 1 -0.221571 0.311746 -0.056870 11.00000 0.01187 0.03178 = 0.02313 0.02196 0.01071 0.01039 AFIX 43 H23 2 -0.306163 0.303254 -0.044382 11.00000 -1.20000 AFIX 0 C24 1 -0.133912 0.263640 -0.006292 11.00000 0.00776 0.01962 = 0.01527 0.01315 0.00467 0.00347 AFIX 43 H24 2 -0.161665 0.224081 0.040008 11.00000 -1.20000 AFIX 0 HKLF 4 REM 161026c in P-1 REM wR2 = 0.1953, GooF = S = 1.081, Restrained GooF = 1.053 for all data REM R1 = 0.0585 for 4232 Fo > 4sig(Fo) and 0.0697 for all 5156 data REM 430 parameters refined using 444 restraints END WGHT 0.1108 61.9294 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+1, -z+1 HTAB O11 O5_$1 HTAB O13 O4 EQIV $2 x, y+1, z HTAB O13 O14_$2 EQIV $3 x, y, z+1 HTAB O14 O11_$3 EQIV $4 -x, -y, -z+1 HTAB O14 O12_$4 EQIV $5 -x+2, -y+1, -z+1 HTAB O15 O2_$5 EQIV $6 x+1, y, z HTAB O15 O3_$6 HTAB O15 O12_$6 HTAB C1 O13_$1 EQIV $7 x-1, y-1, z HTAB C11 O10_$7 HTAB C12 O14_$4 HTAB C13 O13_$1 REM Highest difference peak 4.175, deepest hole -4.097, 1-sigma level 0.433 Q1 1 0.3118 0.4317 0.5951 11.00000 0.05 1.98 Q2 1 0.3717 0.0211 0.9537 11.00000 0.05 1.83 Q3 1 0.5810 0.6040 0.7155 11.00000 0.05 1.60 Q4 1 0.5621 0.7391 0.5572 11.00000 0.05 1.42 Q5 1 0.0100 0.1026 0.0996 11.00000 0.05 1.38 Q6 1 0.2685 0.6521 0.6792 11.00000 0.05 1.33 Q7 1 0.2836 0.0357 0.2584 11.00000 0.05 1.28 Q8 1 0.3051 0.6760 0.6915 11.00000 0.05 1.23 Q9 1 0.6819 0.8378 0.4795 11.00000 0.05 1.21 Q10 1 0.0869 0.3272 -0.1013 11.00000 0.05 1.21 Q11 1 0.7155 0.8234 0.4677 11.00000 0.05 1.17 Q12 1 0.2681 0.4226 0.1787 11.00000 0.05 1.16 Q13 1 0.2829 0.4123 -0.1559 11.00000 0.05 1.07 Q14 1 0.6795 0.7690 0.4513 11.00000 0.05 1.07 Q15 1 0.2082 -0.0398 0.3191 11.00000 0.05 1.07 Q16 1 0.2945 0.4020 -0.1758 11.00000 0.05 1.06 Q17 1 0.3012 -0.0003 0.2742 11.00000 0.05 1.06 Q18 1 -0.1000 0.3832 -0.1256 11.00000 0.05 1.03 Q19 1 0.9144 0.2427 0.3001 11.00000 0.05 1.03 Q20 1 0.2803 -0.1746 0.4384 11.00000 0.05 1.01 ; _shelx_res_checksum 22420 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 W1 W 0.35147(8) 0.45153(8) 0.32830(7) 0.0299(3) Uani 1 1 d . U . . . W2 W 0.36228(7) 0.58847(6) 0.58569(6) 0.0179(2) Uani 1 1 d . U . . . W3 W 0.62263(8) 0.68911(7) 0.49864(7) 0.0272(2) Uani 1 1 d . U . . . Cu1 Cu 0.17348(18) 0.09212(17) 0.19855(16) 0.0114(4) Uani 1 1 d . U . . . Cu2 Cu 0.13457(18) 0.22210(17) 0.05099(15) 0.0101(4) Uani 1 1 d . U . . . N1 N 0.3091(13) 0.0157(12) 0.2451(11) 0.013(3) Uani 1 1 d . . . . . N2 N 0.0652(13) -0.0032(12) 0.2754(11) 0.012(3) Uani 1 1 d . . . . . N3 N 0.2355(13) 0.2918(12) -0.0446(10) 0.011(3) Uani 1 1 d . . . . . N4 N -0.0116(13) 0.2728(12) -0.0225(10) 0.011(3) Uani 1 1 d . . . . . O1 O 0.2391(11) 0.4095(11) 0.1999(9) 0.0170(18) Uani 1 1 d . U . . . O2 O 0.7183(13) 0.7029(12) 0.6424(10) 0.0248(10) Uani 1 1 d . U . . . O3 O 0.2608(11) 0.5231(10) 0.4280(9) 0.0135(16) Uani 1 1 d . U . . . O4 O 0.2605(11) 0.6513(11) 0.6500(9) 0.016(2) Uani 1 1 d . U . . . O5 O 0.5103(11) 0.6154(10) 0.7119(9) 0.0128(16) Uani 1 1 d . U . . . O6 O 0.500000 0.500000 0.500000 0.0139(19) Uani 1 2 d S U P . . O7 O 0.2900(11) 0.4155(10) 0.5709(9) 0.0141(16) Uani 1 1 d . U . . . O8 O 0.4716(13) 0.6105(12) 0.3565(11) 0.0273(9) Uani 1 1 d . U . . . O9 O 0.4809(11) 0.7225(10) 0.5650(9) 0.0129(16) Uani 1 1 d . U . . . O10 O 0.7040(11) 0.8271(11) 0.4941(10) 0.018(2) Uani 1 1 d . U . . . O11 O 0.2683(11) 0.1560(11) 0.1053(9) 0.0153(18) Uani 1 1 d . U . . . H11B H 0.346890 0.212814 0.143411 0.018 Uiso 1 1 d R U . . . O12 O 0.0300(11) 0.1417(11) 0.1306(9) 0.0155(19) Uani 1 1 d . U . . . O13 O 0.4060(14) 0.7922(14) 0.9071(12) 0.036(3) Uani 1 1 d . U . . . H13C H 0.372165 0.746496 0.837324 0.044 Uiso 1 1 d R U . . . H13D H 0.374855 0.850636 0.920014 0.044 Uiso 1 1 d R U . . . O14 O 0.280(2) -0.0232(16) 0.9173(14) 0.063(5) Uani 1 1 d . . . . . H14C H 0.294402 0.038241 0.977123 0.076 Uiso 1 1 d R U . . . H14D H 0.194302 -0.066979 0.892473 0.076 Uiso 1 1 d R U . . . O15 O 0.9787(15) 0.2953(16) 0.3205(16) 0.055(5) Uani 1 1 d . . . . . H15C H 1.062837 0.314793 0.355458 0.066 Uiso 1 1 d R U . . . H15D H 0.962107 0.244213 0.253988 0.066 Uiso 1 1 d R U . . . C1 C 0.4299(17) 0.0279(16) 0.2269(15) 0.020(4) Uani 1 1 d . . . . . H1 H 0.458275 0.072566 0.184346 0.024 Uiso 1 1 calc R U . . . C2 C 0.5154(17) -0.0265(18) 0.2717(16) 0.024(4) Uani 1 1 d . . . . . H2 H 0.598946 -0.017547 0.257072 0.029 Uiso 1 1 calc R U . . . C3 C 0.4799(18) -0.0909(18) 0.3350(16) 0.028(4) Uani 1 1 d . U . . . H3 H 0.538987 -0.123907 0.365634 0.033 Uiso 1 1 calc R U . . . C4 C 0.3477(17) -0.1076(16) 0.3542(14) 0.018(3) Uani 1 1 d . . . . . C5 C 0.2694(15) -0.0502(14) 0.3066(12) 0.011(3) Uani 1 1 d . . . . . C6 C 0.1346(15) -0.0627(14) 0.3206(13) 0.011(3) Uani 1 1 d . . . . . C7 C 0.0835(16) -0.1335(14) 0.3816(13) 0.013(3) Uani 1 1 d . U . . . C8 C 0.1709(19) -0.1865(17) 0.4314(15) 0.024(4) Uani 1 1 d . . . . . H8 H 0.141266 -0.228776 0.475315 0.028 Uiso 1 1 calc R U . . . C9 C 0.2972(19) -0.1760(17) 0.4154(15) 0.024(4) Uani 1 1 d . . . . . H9 H 0.349420 -0.214638 0.445479 0.029 Uiso 1 1 calc R U . . . C10 C -0.0492(17) -0.1427(16) 0.3916(13) 0.020(4) Uani 1 1 d . . . . . H10 H -0.088603 -0.189218 0.429214 0.023 Uiso 1 1 calc R U . . . C11 C -0.1189(17) -0.0816(16) 0.3447(14) 0.019(3) Uani 1 1 d . . . . . H11 H -0.204985 -0.085810 0.352104 0.022 Uiso 1 1 calc R U . . . C12 C -0.0606(17) -0.0127(16) 0.2855(14) 0.019(3) Uani 1 1 d . . . . . H12 H -0.109649 0.026635 0.253123 0.022 Uiso 1 1 calc R U . . . C13 C 0.3592(17) 0.2986(18) -0.0564(14) 0.021(4) Uani 1 1 d . . . . . H13 H 0.409747 0.263457 -0.019809 0.026 Uiso 1 1 calc R U . . . C14 C 0.4148(17) 0.3576(17) -0.1227(15) 0.021(4) Uani 1 1 d . U . . . H14 H 0.500126 0.358741 -0.130077 0.025 Uiso 1 1 calc R U . . . C15 C 0.3467(17) 0.4132(17) -0.1762(14) 0.020(4) Uani 1 1 d . . . . . H15 H 0.385117 0.453953 -0.218215 0.024 Uiso 1 1 calc R U . . . C16 C 0.2138(15) 0.4064(14) -0.1653(12) 0.010(3) Uani 1 1 d . . . . . C17 C 0.1638(15) 0.3439(14) -0.1002(12) 0.010(3) Uani 1 1 d . . . . . C18 C 0.0280(14) 0.3327(14) -0.0886(11) 0.008(3) Uani 1 1 d . . . . . C19 C -0.0506(16) 0.3869(14) -0.1418(13) 0.012(3) Uani 1 1 d . . . . . C20 C 0.0023(17) 0.4493(15) -0.2088(13) 0.016(3) Uani 1 1 d . . . . . H20 H -0.050058 0.483613 -0.244813 0.019 Uiso 1 1 calc R U . . . C21 C 0.1289(16) 0.4587(15) -0.2202(13) 0.017(3) Uani 1 1 d . U . . . H21 H 0.161607 0.499612 -0.264126 0.020 Uiso 1 1 calc R U . . . C22 C -0.1815(16) 0.3723(16) -0.1259(14) 0.019(4) Uani 1 1 d . U . . . H22 H -0.239866 0.402764 -0.161052 0.023 Uiso 1 1 calc R U . . . C23 C -0.2216(16) 0.3117(17) -0.0569(14) 0.018(3) Uani 1 1 d . . . . . H23 H -0.306163 0.303254 -0.044382 0.022 Uiso 1 1 calc R U . . . C24 C -0.1339(15) 0.2636(15) -0.0063(13) 0.013(3) Uani 1 1 d . . . . . H24 H -0.161665 0.224081 0.040008 0.015 Uiso 1 1 calc R U . . . 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 W1 0.0303(4) 0.0327(5) 0.0295(4) 0.0161(4) 0.0079(3) 0.0120(3) W2 0.0195(4) 0.0214(4) 0.0232(4) 0.0134(3) 0.0136(3) 0.0125(3) W3 0.0288(4) 0.0262(4) 0.0324(4) 0.0170(3) 0.0129(3) 0.0101(3) Cu1 0.0109(9) 0.0145(9) 0.0185(9) 0.0149(8) 0.0069(7) 0.0073(7) Cu2 0.0097(9) 0.0151(9) 0.0121(9) 0.0119(8) 0.0043(7) 0.0062(7) N1 0.014(6) 0.012(7) 0.016(7) 0.010(6) 0.004(5) 0.004(5) N2 0.012(6) 0.015(7) 0.019(7) 0.011(6) 0.010(5) 0.010(5) N3 0.009(6) 0.014(7) 0.012(6) 0.004(5) 0.005(5) 0.007(5) N4 0.017(7) 0.009(6) 0.009(6) 0.007(5) 0.004(5) 0.004(5) O1 0.018(3) 0.019(3) 0.021(3) 0.013(3) 0.007(3) 0.010(3) O2 0.0252(13) 0.0243(14) 0.0265(11) 0.0100(10) 0.0104(8) 0.0095(10) O3 0.014(3) 0.019(3) 0.019(3) 0.013(2) 0.011(2) 0.013(2) O4 0.021(5) 0.018(5) 0.023(5) 0.013(4) 0.017(4) 0.013(4) O5 0.014(3) 0.018(3) 0.018(3) 0.012(3) 0.012(3) 0.012(3) O6 0.017(3) 0.017(3) 0.019(3) 0.012(3) 0.013(3) 0.011(3) O7 0.0141(18) 0.0147(18) 0.0144(18) 0.0060(11) 0.0055(11) 0.0055(11) O8 0.0278(12) 0.0278(11) 0.0281(11) 0.0109(10) 0.0103(8) 0.0116(8) O9 0.016(3) 0.017(3) 0.020(3) 0.013(2) 0.013(2) 0.014(2) O10 0.019(5) 0.016(5) 0.024(5) 0.013(4) 0.011(4) 0.007(4) O11 0.015(3) 0.020(4) 0.020(4) 0.013(3) 0.010(3) 0.010(3) O12 0.014(4) 0.021(4) 0.021(4) 0.017(3) 0.006(3) 0.008(3) O13 0.031(6) 0.039(6) 0.030(6) 0.009(5) 0.012(5) 0.004(5) O14 0.118(17) 0.037(9) 0.036(9) 0.010(8) 0.019(10) 0.037(11) O15 0.025(8) 0.057(11) 0.072(12) 0.002(9) 0.019(8) 0.021(8) C1 0.015(8) 0.021(9) 0.033(10) 0.018(8) 0.012(7) 0.008(7) C2 0.010(8) 0.039(11) 0.040(11) 0.031(9) 0.012(7) 0.014(8) C3 0.022(7) 0.032(8) 0.033(8) 0.016(6) 0.001(6) 0.017(6) C4 0.016(8) 0.023(9) 0.023(9) 0.018(8) 0.006(7) 0.011(7) C5 0.008(7) 0.009(7) 0.007(7) -0.001(6) -0.001(6) -0.002(6) C6 0.008(7) 0.010(7) 0.014(7) 0.003(6) 0.005(6) 0.000(6) C7 0.018(6) 0.006(6) 0.017(6) 0.008(5) 0.004(5) 0.003(5) C8 0.028(10) 0.026(10) 0.022(9) 0.019(8) 0.004(7) 0.010(8) C9 0.026(9) 0.027(10) 0.024(9) 0.020(8) 0.002(7) 0.008(8) C10 0.022(9) 0.019(9) 0.012(8) 0.002(7) 0.007(7) 0.002(7) C11 0.016(8) 0.022(9) 0.027(9) 0.016(8) 0.010(7) 0.012(7) C12 0.023(9) 0.019(9) 0.024(9) 0.011(7) 0.016(7) 0.013(7) C13 0.013(8) 0.039(11) 0.023(9) 0.021(8) 0.010(7) 0.011(8) C14 0.012(6) 0.028(7) 0.030(7) 0.016(6) 0.011(6) 0.009(6) C15 0.018(8) 0.029(10) 0.022(9) 0.014(8) 0.016(7) 0.009(7) C16 0.010(7) 0.015(8) 0.007(7) 0.007(6) 0.002(6) 0.003(6) C17 0.015(8) 0.008(7) 0.004(7) 0.001(6) 0.002(6) 0.002(6) C18 0.006(7) 0.013(8) 0.002(6) 0.002(6) 0.001(5) 0.003(6) C19 0.015(8) 0.010(7) 0.012(7) 0.004(6) 0.006(6) 0.005(6) C20 0.025(9) 0.017(8) 0.012(8) 0.012(7) 0.007(7) 0.008(7) C21 0.017(3) 0.017(3) 0.016(3) 0.0069(16) 0.0050(14) 0.0059(16) C22 0.013(6) 0.022(7) 0.024(7) 0.007(6) 0.002(5) 0.013(6) C23 0.012(8) 0.032(10) 0.023(9) 0.022(8) 0.011(7) 0.010(7) C24 0.008(7) 0.020(8) 0.015(8) 0.013(7) 0.005(6) 0.003(6) 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' W W -0.8490 6.8722 '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 W1 O8 103.1(5) . . ? O1 W1 O3 102.4(5) . . ? O8 W1 O3 90.1(5) . . ? O1 W1 O5 101.6(5) . 2_666 ? O8 W1 O5 89.3(5) . 2_666 ? O3 W1 O5 155.4(4) . 2_666 ? O1 W1 O2 100.8(5) . 2_666 ? O8 W1 O2 155.9(5) . 2_666 ? O3 W1 O2 87.1(5) . 2_666 ? O5 W1 O2 83.6(5) 2_666 2_666 ? O1 W1 O6 177.8(4) . . ? O8 W1 O6 79.0(4) . . ? O3 W1 O6 78.2(3) . . ? O5 W1 O6 77.6(3) 2_666 . ? O2 W1 O6 77.0(4) 2_666 . ? O1 W1 W3 136.5(4) . . ? O8 W1 W3 33.4(4) . . ? O3 W1 W3 84.1(3) . . ? O5 W1 W3 82.0(3) 2_666 . ? O2 W1 W3 122.5(4) 2_666 . ? O6 W1 W3 45.59(2) . . ? O4 W2 O9 103.7(5) . . ? O4 W2 O5 102.0(5) . . ? O9 W2 O5 88.7(5) . . ? O4 W2 O3 103.4(5) . . ? O9 W2 O3 87.9(5) . . ? O5 W2 O3 154.5(4) . . ? O4 W2 O7 102.6(5) . . ? O9 W2 O7 153.7(4) . . ? O5 W2 O7 86.8(4) . . ? O3 W2 O7 85.1(5) . . ? O4 W2 O6 178.8(4) . . ? O9 W2 O6 77.3(3) . . ? O5 W2 O6 77.4(3) . . ? O3 W2 O6 77.2(3) . . ? O7 W2 O6 76.4(3) . . ? O10 W3 O7 104.1(5) . 2_666 ? O10 W3 O2 104.0(6) . . ? O7 W3 O2 90.6(5) 2_666 . ? O10 W3 O9 101.9(5) . . ? O7 W3 O9 153.8(5) 2_666 . ? O2 W3 O9 86.3(5) . . ? O10 W3 O8 100.8(5) . . ? O7 W3 O8 87.8(5) 2_666 . ? O2 W3 O8 154.7(6) . . ? O9 W3 O8 84.0(5) . . ? O10 W3 O6 176.9(4) . . ? O7 W3 O6 77.7(3) 2_666 . ? O2 W3 O6 78.4(4) . . ? O9 W3 O6 76.2(3) . . ? O8 W3 O6 76.6(4) . . ? O10 W3 W1 132.4(4) . . ? O7 W3 W1 81.2(3) 2_666 . ? O2 W3 W1 123.4(4) . . ? O9 W3 W1 78.8(3) . . ? O8 W3 W1 31.5(4) . . ? O6 W3 W1 45.10(2) . . ? O11 Cu1 O12 83.2(4) . . ? O11 Cu1 N1 95.1(5) . . ? O12 Cu1 N1 170.6(5) . . ? O11 Cu1 N2 170.4(5) . . ? O12 Cu1 N2 98.2(5) . . ? N1 Cu1 N2 82.0(5) . . ? O12 Cu2 O11 83.3(4) . . ? O12 Cu2 N4 97.5(5) . . ? O11 Cu2 N4 173.2(5) . . ? O12 Cu2 N3 174.9(5) . . ? O11 Cu2 N3 96.6(5) . . ? N4 Cu2 N3 81.9(5) . . ? O12 Cu2 O1 94.2(4) . . ? O11 Cu2 O1 92.7(4) . . ? N4 Cu2 O1 93.9(4) . . ? N3 Cu2 O1 90.9(5) . . ? C1 N1 C5 118.9(14) . . ? C1 N1 Cu1 128.3(11) . . ? C5 N1 Cu1 112.8(10) . . ? C12 N2 C6 119.3(13) . . ? C12 N2 Cu1 128.7(11) . . ? C6 N2 Cu1 112.0(9) . . ? C13 N3 C17 117.4(13) . . ? C13 N3 Cu2 130.5(11) . . ? C17 N3 Cu2 112.0(9) . . ? C24 N4 C18 118.0(13) . . ? C24 N4 Cu2 128.3(10) . . ? C18 N4 Cu2 113.5(10) . . ? W1 O1 Cu2 131.1(6) . . ? W3 O2 W1 113.7(6) . 2_666 ? W1 O3 W2 114.8(5) . . ? W2 O5 W1 114.5(5) . 2_666 ? W1 O6 W1 180.0 2_666 . ? W1 O6 W3 90.69(3) 2_666 . ? W1 O6 W3 89.31(3) . . ? W1 O6 W3 89.31(3) 2_666 2_666 ? W1 O6 W3 90.69(3) . 2_666 ? W3 O6 W3 180.0 . 2_666 ? W1 O6 W2 90.41(3) 2_666 . ? W1 O6 W2 89.59(3) . . ? W3 O6 W2 90.10(3) . . ? W3 O6 W2 89.90(3) 2_666 . ? W1 O6 W2 89.59(3) 2_666 2_666 ? W1 O6 W2 90.41(3) . 2_666 ? W3 O6 W2 89.90(3) . 2_666 ? W3 O6 W2 90.10(3) 2_666 2_666 ? W2 O6 W2 179.999(18) . 2_666 ? W3 O7 W2 116.1(5) 2_666 . ? W1 O8 W3 115.0(7) . . ? W2 O9 W3 116.3(5) . . ? Cu1 O11 Cu2 96.6(5) . . ? Cu1 O11 H11B 112.3 . . ? Cu2 O11 H11B 112.2 . . ? Cu2 O12 Cu1 96.3(5) . . ? H13C O13 H13D 108.1 . . ? H14C O14 H14D 107.9 . . ? H15C O15 H15D 107.6 . . ? N1 C1 C2 120.5(15) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 122.1(15) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 118.4(15) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C9 C4 C5 120.6(15) . . ? C9 C4 C3 123.8(15) . . ? C5 C4 C3 115.6(14) . . ? N1 C5 C4 124.4(14) . . ? N1 C5 C6 116.0(14) . . ? C4 C5 C6 119.5(14) . . ? N2 C6 C7 123.4(13) . . ? N2 C6 C5 117.0(13) . . ? C7 C6 C5 119.5(14) . . ? C10 C7 C6 116.7(14) . . ? C10 C7 C8 125.2(15) . . ? C6 C7 C8 118.1(14) . . ? C9 C8 C7 121.6(15) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C4 120.5(16) . . ? C8 C9 H9 119.7 . . ? C4 C9 H9 119.7 . . ? C11 C10 C7 119.2(15) . . ? C11 C10 H10 120.4 . . ? C7 C10 H10 120.4 . . ? C10 C11 C12 120.7(15) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? N2 C12 C11 120.7(15) . . ? N2 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? N3 C13 C14 121.8(15) . . ? N3 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C15 C14 C13 121.7(15) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C16 117.5(15) . . ? C14 C15 H15 121.3 . . ? C16 C15 H15 121.3 . . ? C17 C16 C15 117.6(14) . . ? C17 C16 C21 119.2(14) . . ? C15 C16 C21 123.2(14) . . ? N3 C17 C16 123.9(14) . . ? N3 C17 C18 116.6(13) . . ? C16 C17 C18 119.5(13) . . ? N4 C18 C19 124.5(13) . . ? N4 C18 C17 115.8(13) . . ? C19 C18 C17 119.7(13) . . ? C18 C19 C22 116.1(14) . . ? C18 C19 C20 119.7(14) . . ? C22 C19 C20 124.1(15) . . ? C21 C20 C19 120.5(15) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C16 121.5(15) . . ? C20 C21 H21 119.3 . . ? C16 C21 H21 119.3 . . ? C23 C22 C19 119.2(15) . . ? C23 C22 H22 120.4 . . ? C19 C22 H22 120.4 . . ? C22 C23 C24 119.8(14) . . ? C22 C23 H23 120.1 . . ? C24 C23 H23 120.1 . . ? N4 C24 C23 122.2(14) . . ? N4 C24 H24 118.9 . . ? C23 C24 H24 118.9 . . ? 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 W1 O1 1.700(11) . ? W1 O8 1.863(13) . ? W1 O3 1.915(10) . ? W1 O5 1.955(10) 2_666 ? W1 O2 2.000(13) 2_666 ? W1 O6 2.2870(8) . ? W1 W3 3.2285(12) . ? W2 O4 1.701(10) . ? W2 O9 1.890(11) . ? W2 O5 1.928(11) . ? W2 O3 1.932(11) . ? W2 O7 1.953(11) . ? W2 O6 2.3145(7) . ? W3 O10 1.680(11) . ? W3 O7 1.895(11) 2_666 ? W3 O2 1.903(13) . ? W3 O9 1.961(10) . ? W3 O8 1.964(13) . ? W3 O6 2.3065(8) . ? Cu1 O11 1.942(11) . ? Cu1 O12 1.958(10) . ? Cu1 N1 2.025(13) . ? Cu1 N2 2.033(13) . ? Cu2 O12 1.943(11) . ? Cu2 O11 1.949(11) . ? Cu2 N4 2.019(13) . ? Cu2 N3 2.035(13) . ? Cu2 O1 2.280(12) . ? N1 C1 1.33(2) . ? N1 C5 1.35(2) . ? N2 C12 1.35(2) . ? N2 C6 1.35(2) . ? N3 C13 1.34(2) . ? N3 C17 1.368(19) . ? N4 C24 1.34(2) . ? N4 C18 1.356(19) . ? O11 H11B 0.8499 . ? O13 H13C 0.8501 . ? O13 H13D 0.8500 . ? O14 H14C 0.8500 . ? O14 H14D 0.8500 . ? O15 H15C 0.8500 . ? O15 H15D 0.8500 . ? C1 C2 1.41(2) . ? C1 H1 0.9300 . ? C2 C3 1.35(3) . ? C2 H2 0.9300 . ? C3 C4 1.45(2) . ? C3 H3 0.9300 . ? C4 C9 1.40(2) . ? C4 C5 1.41(2) . ? C5 C6 1.45(2) . ? C6 C7 1.42(2) . ? C7 C10 1.42(2) . ? C7 C8 1.44(2) . ? C8 C9 1.38(3) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.38(2) . ? C10 H10 0.9300 . ? C11 C12 1.41(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.41(2) . ? C13 H13 0.9300 . ? C14 C15 1.36(2) . ? C14 H14 0.9300 . ? C15 C16 1.43(2) . ? C15 H15 0.9300 . ? C16 C17 1.40(2) . ? C16 C21 1.45(2) . ? C17 C18 1.46(2) . ? C18 C19 1.41(2) . ? C19 C22 1.42(2) . ? C19 C20 1.43(2) . ? C20 C21 1.36(2) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.39(2) . ? C22 H22 0.9300 . ? C23 C24 1.40(2) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ?