# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2001 # CCDC Number: 186/2336 data_global #==================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Long, La-Sheng School of Chemistry and Chemical Engineering Xiamen University Xiamen, 361005 P. R. China ; _publ_contact_author_phone '86-592-2185191' _publ_contact_author_email lslong@xmu.edu.cn _publ_requested_joiurnal 'J. Chem. Soc.; Dalton Trans.' _publ_requested_coeditor_name ? _publ_contact_letter ; Dear Sir or Madam: Please consider this CIF as a supplmentary data for a manuscript submitted to J. Chem. Soc.; Dalton Trans. La-Sheng Long ; #================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Hydrogen bonds induced the change of geometry and crystallized forms of copper(II) complexes: Synthesis and crystal structure of copper(II) complexes with Schiff-base ligands containing two imidazolyl group perchlorate heptahydrate ; loop_ _publ_author_name _publ_author_address 'Long, La-Sheng' ; School of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 P. R. China ; 'Cai, Ji-Wen' ; School of Chemistry and Chemical Engineering Zhongshan University Guangzhou 510275 P. R. China 'Ren, Yan-Ping' ; School of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 P. R. China 'Tong, Ye-Xiang' ; School of Chemistry and Chemical Engineering Zhongshan University Guangzhou 510275 P. R. China ; 'Chen, Xiao-Ming' ; School of Chemistry and Chemical Engineering Zhongshan University Guangzhou 510275 P. R. China 'Ji, Liang-Nian' ; School of Chemistry and Chemical Engineering Zhongshan University Guangzhou 510275 P. R. China 'Huang, Rong-Bin' ; School of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 P. R. China 'Zheng, Lan-Sun' ; School of Chemistry and Chemical Engineering Xiamen University Xiamen 361005 P. R. China ; #============================================================ data_complex1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H29 Cl2 Cu N7 O9' _chemical_formula_weight 609.91 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' '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 18.038(4) _cell_length_b 8.589(2) _cell_length_c 18.183(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.62(2) _cell_angle_gamma 90.00 _cell_volume 2581.1(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.570 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1260 _exptl_absorpt_coefficient_mu 1.113 _exptl_absorpt_correction_type 'semi-empirical' _exptl_absorpt_correction_T_min 0.6286 _exptl_absorpt_correction_T_max 0.7607 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens R3m' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 120 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 3232 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0834 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3232 _reflns_number_gt 2065 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1990)' _computing_cell_refinement 'SHELXTL-Plus (Sheldrick, 1990)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_solution 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1674P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3232 _refine_ls_number_parameters 361 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.1135 _refine_ls_R_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.2424 _refine_ls_wR_factor_gt 0.2135 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.090 _refine_ls_shift/su_mean 0.008 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.26113(4) 0.00442(6) 0.00870(4) 0.0629(2) Uani 1 1 d . . . N1 N 0.2302(2) 0.1731(4) 0.0695(2) 0.0646(12) Uani 1 1 d . . . N2 N 0.1995(3) 0.3730(5) 0.1271(3) 0.0758(13) Uani 1 1 d . . . H2A H 0.1703 0.4480 0.1376 0.080 Uiso 1 1 d R . . N3 N 0.3690(3) 0.0326(5) 0.0995(3) 0.0763(14) Uani 1 1 d . . . N4 N 0.2786(3) -0.2219(5) -0.0127(3) 0.0872(16) Uani 1 1 d . . . N5 N 0.1498(3) -0.0141(5) -0.0722(3) 0.0727(14) Uani 1 1 d . . . N6 N 0.2605(3) 0.3516(4) -0.1659(3) 0.0849(14) Uani 1 1 d . . . H6C H 0.2756 0.4283 -0.1907 0.080 Uiso 1 1 d R . . N7 N 0.2677(2) 0.1659(4) -0.0815(2) 0.0633(12) Uani 1 1 d . . . C1 C 0.1700(3) 0.2686(6) 0.0646(3) 0.0731(16) Uani 1 1 d . . . H1A H 0.1158 0.2636 0.0242 0.080 Uiso 1 1 d R . . C2 C 0.2790(3) 0.3467(6) 0.1702(3) 0.0736(15) Uani 1 1 d . . . C3 C 0.3293(4) 0.4475(7) 0.2393(4) 0.101(2) Uani 1 1 d . . . H3A H 0.3843 0.4118 0.2621 0.080 Uiso 1 1 d R . . H3B H 0.3278 0.5541 0.2229 0.080 Uiso 1 1 d R . . H3C H 0.3065 0.4395 0.2787 0.080 Uiso 1 1 d R . . C4 C 0.2972(3) 0.2225(5) 0.1331(3) 0.0629(14) Uani 1 1 d . . . C5 C 0.3712(3) 0.1410(6) 0.1480(3) 0.0712(16) Uani 1 1 d . . . H5A H 0.4201 0.1656 0.1935 0.080 Uiso 1 1 d R . . C6 C 0.4414(4) -0.0555(7) 0.1139(4) 0.099(2) Uani 1 1 d . . . H6A H 0.4621 -0.1005 0.1667 0.080 Uiso 1 1 d R . . H6B H 0.4815 0.0145 0.1108 0.080 Uiso 1 1 d R . . C7 C 0.4301(4) -0.1819(7) 0.0546(4) 0.109(2) Uani 1 1 d . . . H7A H 0.4784 -0.2433 0.0697 0.080 Uiso 1 1 d R . . H7B H 0.4213 -0.1333 0.0043 0.080 Uiso 1 1 d R . . C8 C 0.3598(4) -0.2820(6) 0.0370(5) 0.116(3) Uani 1 1 d . . . H8A H 0.3693 -0.3761 0.0136 0.080 Uiso 1 1 d R . . H8B H 0.3590 -0.3085 0.0880 0.080 Uiso 1 1 d R . . C9 C 0.2760(5) -0.2303(8) -0.1012(4) 0.123(3) Uani 1 1 d . . . H9A H 0.2840 -0.3357 -0.1141 0.080 Uiso 1 1 d R . . H9B H 0.2234 -0.1953 -0.1372 0.080 Uiso 1 1 d R . . H9C H 0.3166 -0.1647 -0.1066 0.080 Uiso 1 1 d R . . C10 C 0.2167(5) -0.3197(8) -0.0071(5) 0.122(3) Uani 1 1 d . . . H10A H 0.2186 -0.3108 0.0462 0.080 Uiso 1 1 d R . . H10B H 0.2292 -0.4260 -0.0140 0.080 Uiso 1 1 d R . . C11 C 0.1310(4) -0.2899(7) -0.0634(5) 0.127(3) Uani 1 1 d . . . H11A H 0.1276 -0.3083 -0.1167 0.080 Uiso 1 1 d R . . H11B H 0.0974 -0.3662 -0.0531 0.080 Uiso 1 1 d R . . C12 C 0.0973(4) -0.1291(8) -0.0623(5) 0.116(3) Uani 1 1 d . . . H12A H 0.0456 -0.1193 -0.1065 0.080 Uiso 1 1 d R . . H12B H 0.0900 -0.1145 -0.0132 0.080 Uiso 1 1 d R . . C13 C 0.1291(3) 0.0761(7) -0.1348(3) 0.0780(18) Uani 1 1 d . . . H13A H 0.0754 0.0723 -0.1761 0.080 Uiso 1 1 d R . . C14 C 0.1880(3) 0.1785(6) -0.1397(3) 0.0703(15) Uani 1 1 d . . . C15 C 0.1819(4) 0.2909(6) -0.1928(4) 0.0821(17) Uani 1 1 d . . . C16 C 0.1155(4) 0.3577(8) -0.2632(4) 0.105(2) Uani 1 1 d . . . H16A H 0.0668 0.3015 -0.2713 0.080 Uiso 1 1 d R . . H16B H 0.1084 0.4655 -0.2536 0.080 Uiso 1 1 d R . . H16C H 0.1271 0.3484 -0.3101 0.080 Uiso 1 1 d R . . C17 C 0.3094(3) 0.2742(6) -0.1004(4) 0.0762(16) Uani 1 1 d . . . H17A H 0.3657 0.2961 -0.0702 0.080 Uiso 1 1 d R . . Cl1 Cl 0.05918(8) 0.66886(17) 0.15075(10) 0.0862(5) Uani 1 1 d D . . O11A O 0.0008(4) 0.7434(9) 0.0832(4) 0.190(6) Uani 0.60 1 d PD . . O12A O 0.0394(5) 0.5090(6) 0.1544(6) 0.207(7) Uani 0.60 1 d PD . . O13A O 0.0638(4) 0.7459(7) 0.2230(3) 0.116(3) Uani 0.60 1 d PD . . O14A O 0.1377(3) 0.6790(8) 0.1481(4) 0.110(3) Uani 0.60 1 d PD . . O11B O 0.0326(6) 0.5468(8) 0.0906(5) 0.234(9) Uani 0.40 1 d PD . . O12B O 0.0183(4) 0.6520(13) 0.2026(4) 0.221(7) Uani 0.40 1 d PD . . O13B O 0.1445(3) 0.6543(13) 0.1944(6) 0.159(7) Uani 0.40 1 d PD . . O14B O 0.0394(6) 0.8150(7) 0.1105(5) 0.135(5) Uani 0.40 1 d PD . . Cl2 Cl 0.53437(10) -0.59854(18) 0.14852(10) 0.0928(5) Uani 1 1 d . . . O21 O 0.5784(4) -0.4747(7) 0.1428(5) 0.181(3) Uani 1 1 d . . . O22 O 0.5730(3) -0.7119(7) 0.1986(4) 0.165(3) Uani 1 1 d . . . O23 O 0.4774(4) -0.5333(7) 0.1756(4) 0.144(2) Uani 1 1 d . . . O24 O 0.4923(5) -0.6643(9) 0.0722(4) 0.191(3) Uani 1 1 d . . . O1W O 0.2603(3) 0.5979(6) -0.2802(4) 0.157(2) Uani 1 1 d . . . H1WA H 0.2519 0.6868 -0.2585 0.080 Uiso 1 1 d R . . H1WB H 0.3031 0.5651 -0.2429 0.080 Uiso 1 1 d R . . 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 Cu1 0.0589(4) 0.0550(4) 0.0696(4) -0.0045(3) 0.0202(3) -0.0008(2) N1 0.067(2) 0.057(2) 0.068(2) -0.0113(18) 0.026(2) -0.0008(19) N2 0.085(3) 0.063(2) 0.087(3) -0.008(2) 0.042(2) 0.009(2) N3 0.065(3) 0.077(3) 0.073(3) -0.023(2) 0.013(2) 0.002(2) N4 0.105(3) 0.049(2) 0.093(3) 0.005(2) 0.025(3) -0.004(2) N5 0.052(2) 0.082(3) 0.068(3) 0.000(2) 0.007(2) -0.006(2) N6 0.135(3) 0.048(2) 0.093(3) 0.0155(19) 0.068(3) 0.013(2) N7 0.065(2) 0.052(2) 0.070(3) 0.0018(18) 0.024(2) 0.0001(18) C1 0.070(3) 0.077(3) 0.074(3) 0.003(3) 0.031(3) 0.013(3) C2 0.092(3) 0.067(3) 0.079(3) -0.004(2) 0.052(3) -0.009(3) C3 0.124(4) 0.081(3) 0.115(4) -0.036(3) 0.067(4) -0.023(3) C4 0.068(3) 0.046(2) 0.080(3) 0.002(2) 0.036(3) -0.001(2) C5 0.069(3) 0.066(3) 0.077(3) -0.008(3) 0.028(3) -0.008(3) C6 0.068(3) 0.107(4) 0.115(5) -0.006(4) 0.030(4) 0.027(3) C7 0.104(4) 0.104(4) 0.120(5) -0.001(4) 0.045(4) 0.035(4) C8 0.147(6) 0.063(3) 0.127(6) 0.012(3) 0.042(5) 0.035(4) C9 0.149(6) 0.106(5) 0.102(5) -0.026(4) 0.039(5) 0.015(4) C10 0.127(5) 0.086(4) 0.136(6) 0.012(4) 0.036(5) -0.011(4) C11 0.153(5) 0.086(4) 0.148(6) -0.003(4) 0.067(5) -0.065(4) C12 0.091(4) 0.146(5) 0.107(5) -0.015(4) 0.035(4) -0.054(4) C13 0.060(3) 0.093(4) 0.065(4) -0.012(3) 0.008(3) -0.002(3) C14 0.077(3) 0.062(3) 0.075(3) 0.009(2) 0.033(3) 0.013(3) C15 0.088(3) 0.082(3) 0.080(4) 0.011(3) 0.037(3) 0.028(3) C16 0.109(5) 0.110(4) 0.084(4) 0.025(3) 0.026(4) 0.043(4) C17 0.083(3) 0.070(3) 0.086(4) 0.003(3) 0.045(3) 0.002(3) Cl1 0.0713(8) 0.0827(9) 0.0993(11) -0.0073(8) 0.0287(8) 0.0061(7) O11A 0.101(7) 0.290(14) 0.135(10) 0.005(9) 0.002(7) 0.065(8) O12A 0.217(11) 0.160(10) 0.278(15) 0.006(8) 0.133(11) -0.038(8) O13A 0.117(5) 0.120(5) 0.118(6) -0.035(4) 0.055(5) -0.019(5) O14A 0.067(4) 0.150(6) 0.105(6) -0.040(5) 0.026(4) -0.002(4) O11B 0.172(13) 0.152(11) 0.42(2) -0.148(13) 0.156(14) -0.087(10) O12B 0.229(12) 0.250(17) 0.267(15) 0.124(13) 0.186(11) 0.134(12) O13B 0.181(15) 0.189(13) 0.075(9) -0.023(9) 0.017(10) 0.025(12) O14B 0.145(10) 0.118(9) 0.166(12) 0.026(8) 0.088(9) 0.019(8) Cl2 0.0990(9) 0.0835(9) 0.1094(10) 0.0176(8) 0.0560(9) -0.0002(8) O21 0.131(5) 0.157(4) 0.213(6) 0.098(4) 0.025(5) -0.023(4) O22 0.123(4) 0.146(4) 0.222(6) 0.066(4) 0.064(4) 0.035(3) O23 0.153(4) 0.161(4) 0.146(4) -0.001(3) 0.089(3) 0.036(3) O24 0.205(6) 0.237(7) 0.118(4) -0.055(4) 0.051(5) 0.003(6) O1W 0.142(4) 0.122(4) 0.191(6) 0.030(4) 0.051(4) 0.035(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cu1 N5 1.964(4) . yes Cu1 N3 2.000(4) . yes Cu1 N1 2.032(4) . yes Cu1 N4 2.032(4) . yes Cu1 N7 2.187(4) . yes N1 C1 1.335(6) . ? N1 C4 1.363(6) . ? N2 C2 1.349(6) . ? N2 C1 1.376(6) . ? N3 C5 1.272(7) . ? N3 C6 1.439(7) . ? N4 C10 1.432(9) . ? N4 C8 1.473(8) . ? N4 C9 1.593(9) . ? N5 C13 1.302(7) . ? N5 C12 1.429(8) . ? N6 C17 1.340(7) . ? N6 C15 1.402(7) . ? N7 C17 1.325(7) . ? N7 C14 1.406(6) . ? C2 C4 1.370(7) . ? C2 C3 1.496(7) . ? C4 C5 1.434(7) . ? C6 C7 1.485(9) . ? C7 C8 1.457(9) . ? C10 C11 1.496(10) . ? C11 C12 1.512(9) . ? C13 C14 1.409(8) . ? C14 C15 1.338(8) . ? C15 C16 1.474(8) . ? Cl1 O11A 1.411(5) . ? Cl1 O12B 1.417(6) . ? Cl1 O14B 1.424(6) . ? Cl1 O13B 1.426(5) . ? Cl1 O12A 1.426(5) . ? Cl1 O14A 1.438(5) . ? Cl1 O13A 1.444(5) . ? Cl1 O11B 1.450(6) . ? O11A O14B 0.912(11) . ? O11A O11B 1.771(10) . ? O12A O11B 1.162(13) . ? O12A O12B 1.639(13) . ? O13A O12B 1.103(11) . ? O14A O13B 0.828(12) . ? Cl2 O22 1.325(6) . ? Cl2 O21 1.356(6) . ? Cl2 O24 1.406(6) . ? Cl2 O23 1.421(6) . ? 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 N5 Cu1 N3 173.5(2) . . ? N5 Cu1 N1 92.53(18) . . ? N3 Cu1 N1 81.53(17) . . ? N5 Cu1 N4 88.25(18) . . ? N3 Cu1 N4 95.73(18) . . ? N1 Cu1 N4 152.1(2) . . ? N5 Cu1 N7 80.57(17) . . ? N3 Cu1 N7 102.44(17) . . ? N1 Cu1 N7 93.74(16) . . ? N4 Cu1 N7 113.81(19) . . ? C1 N1 C4 106.6(4) . . ? C1 N1 Cu1 142.7(3) . . ? C4 N1 Cu1 109.9(3) . . ? C2 N2 C1 109.9(4) . . ? C5 N3 C6 119.0(5) . . ? C5 N3 Cu1 114.3(4) . . ? C6 N3 Cu1 126.7(4) . . ? C10 N4 C8 111.3(5) . . ? C10 N4 C9 109.7(5) . . ? C8 N4 C9 102.9(6) . . ? C10 N4 Cu1 111.3(5) . . ? C8 N4 Cu1 114.2(4) . . ? C9 N4 Cu1 107.0(3) . . ? C13 N5 C12 123.4(5) . . ? C13 N5 Cu1 117.1(4) . . ? C12 N5 Cu1 119.5(4) . . ? C17 N6 C15 109.8(5) . . ? C17 N7 C14 105.4(4) . . ? C17 N7 Cu1 147.8(3) . . ? C14 N7 Cu1 105.5(3) . . ? N1 C1 N2 108.1(4) . . ? N2 C2 C4 104.7(4) . . ? N2 C2 C3 122.4(5) . . ? C4 C2 C3 132.8(5) . . ? N1 C4 C2 110.7(4) . . ? N1 C4 C5 116.7(4) . . ? C2 C4 C5 132.5(5) . . ? N3 C5 C4 117.3(5) . . ? N3 C6 C7 113.7(5) . . ? C8 C7 C6 116.5(6) . . ? C7 C8 N4 119.5(5) . . ? N4 C10 C11 118.2(6) . . ? C10 C11 C12 117.2(6) . . ? N5 C12 C11 109.8(6) . . ? N5 C13 C14 117.9(5) . . ? C15 C14 N7 111.3(5) . . ? C15 C14 C13 130.5(5) . . ? N7 C14 C13 118.2(5) . . ? C14 C15 N6 103.7(5) . . ? C14 C15 C16 135.3(6) . . ? N6 C15 C16 121.0(5) . . ? N7 C17 N6 109.8(5) . . ? O12B Cl1 O14B 110.0(5) . . ? O12B Cl1 O13B 110.6(5) . . ? O14B Cl1 O13B 110.8(5) . . ? O11A Cl1 O12A 111.3(4) . . ? O11A Cl1 O14A 110.2(4) . . ? O12A Cl1 O14A 109.1(4) . . ? O11A Cl1 O13A 109.6(4) . . ? O12A Cl1 O13A 108.8(5) . . ? O14A Cl1 O13A 107.7(3) . . ? O12B Cl1 O11B 108.9(5) . . ? O14B Cl1 O11B 108.1(5) . . ? O13B Cl1 O11B 108.3(5) . . ? O22 Cl2 O21 117.8(4) . . ? O22 Cl2 O24 108.1(4) . . ? O21 Cl2 O24 109.9(5) . . ? O22 Cl2 O23 107.8(4) . . ? O21 Cl2 O23 104.1(4) . . ? O24 Cl2 O23 108.8(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O14A 0.90 2.10 2.939(8) 154.8 . N2 H2A O13B 0.90 2.19 3.049(11) 158.6 . N6 H6C O1W 0.90 2.12 2.965(7) 156.3 . N6 H6C O21 0.90 2.45 2.961(8) 116.0 3_655 O1W H1WA O13B 0.90 2.24 2.887(11) 128.4 4_575 O1W H1WB O22 0.85 2.41 2.937(8) 121.4 3_655 _diffrn_measured_fraction_theta_max 0.711 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.711 _refine_diff_density_max 0.888 _refine_diff_density_min -0.565 _refine_diff_density_rms 0.097 #============================================================END data_complex2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H27 Cu F12 N7 P2' _chemical_formula_weight 682.94 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_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' _cell_length_a 20.424(4) _cell_length_b 8.6320(17) _cell_length_c 18.313(4) _cell_angle_alpha 90.00 _cell_angle_beta 122.16(3) _cell_angle_gamma 90.00 _cell_volume 2733.2(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour deep blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.660 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1380 _exptl_absorpt_coefficient_mu 1.020 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens R3m' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5469 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.02 _reflns_number_total 2983 _reflns_number_gt 2186 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1990)' _computing_cell_refinement 'SHELXTL-Plus (Sheldrick, 1990)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_solution 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1182P)^2^+9.5234P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2983 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1019 _refine_ls_R_factor_gt 0.0796 _refine_ls_wR_factor_ref 0.2434 _refine_ls_wR_factor_gt 0.2301 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.99150(10) 0.2500 0.0574(4) Uani 1 2 d S . . N2 N 0.1413(3) 0.6346(6) 0.4273(4) 0.0748(14) Uani 1 1 d . . . H2B H 0.1562 0.5611 0.4646 0.090 Uiso 1 1 calc R . . N1 N 0.0728(2) 0.8276(5) 0.3446(3) 0.0549(10) Uani 1 1 d . . . N3 N 0.0838(4) 0.9825(6) 0.2272(4) 0.0745(14) Uani 1 1 d . . . N4 N 0.0000 1.2214(9) 0.2500 0.156(6) Uani 1 2 d S . . C1 C 0.0793(3) 0.7262(7) 0.4017(4) 0.0654(14) Uani 1 1 d . . . H1A H 0.0460 0.7188 0.4215 0.078 Uiso 1 1 calc R . . C2 C 0.1768(3) 0.6767(7) 0.3847(4) 0.0664(14) Uani 1 1 d . . . C3 C 0.2468(5) 0.5953(9) 0.3971(6) 0.097(2) Uani 1 1 d . . . H3A H 0.2627 0.6433 0.3617 0.146 Uiso 1 1 calc R . . H3B H 0.2346 0.4885 0.3810 0.146 Uiso 1 1 calc R . . H3C H 0.2879 0.6020 0.4566 0.146 Uiso 1 1 calc R . . C4 C 0.1344(3) 0.7956(6) 0.3340(4) 0.0569(12) Uani 1 1 d . . . C5 C 0.1370(4) 0.8874(7) 0.2699(4) 0.0700(16) Uani 1 1 d . . . H5A H 0.1772 0.8761 0.2605 0.084 Uiso 1 1 calc R . . C6 C 0.0834(7) 1.0857(11) 0.1620(7) 0.123(4) Uani 1 1 d . . . H6A H 0.1341 1.0825 0.1695 0.148 Uiso 1 1 calc R . . H6B H 0.0465 1.0453 0.1050 0.148 Uiso 1 1 calc R . . C7 C 0.0653(8) 1.2351(11) 0.1655(10) 0.156(5) Uani 1 1 d . . . H7A H 0.0366 1.2698 0.1060 0.188 Uiso 1 1 calc R . . H7B H 0.1142 1.2899 0.1931 0.188 Uiso 1 1 calc R . . C8 C 0.0253(5) 1.2984(9) 0.2023(8) 0.115(3) Uani 1 1 d . . . H8A H 0.0578 1.3823 0.2390 0.138 Uiso 1 1 calc R . . H8B H -0.0205 1.3469 0.1548 0.138 Uiso 1 1 calc R . . C9 C 0.0982(9) 1.2386(19) 0.3488(12) 0.108(6) Uani 0.50 1 d P . . H9A H 0.1111 1.3461 0.3621 0.162 Uiso 0.50 1 calc PR . . H9B H 0.1352 1.1897 0.3393 0.162 Uiso 0.50 1 calc PR . . H9C H 0.0989 1.1890 0.3961 0.162 Uiso 0.50 1 calc PR . . P1 P -0.15086(11) 0.6342(2) 0.40241(13) 0.0808(6) Uani 1 1 d . . . F1 F -0.1816(5) 0.4657(9) 0.3697(6) 0.172(3) Uani 1 1 d . . . F2 F -0.1173(6) 0.7948(8) 0.4387(7) 0.221(4) Uani 1 1 d . . . F3 F -0.2203(3) 0.7186(11) 0.3233(5) 0.196(4) Uani 1 1 d . . . F4 F -0.2014(4) 0.6243(9) 0.4431(5) 0.188(4) Uani 1 1 d . . . F5 F -0.1050(4) 0.6287(8) 0.3569(4) 0.145(2) Uani 1 1 d . . . F6 F -0.0818(3) 0.5507(8) 0.4835(4) 0.134(2) Uani 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 Cu1 0.0667(6) 0.0494(5) 0.0726(6) 0.000 0.0481(5) 0.000 N2 0.082(3) 0.065(3) 0.082(3) 0.021(3) 0.047(3) 0.019(3) N1 0.053(2) 0.059(2) 0.062(2) 0.007(2) 0.037(2) 0.0061(19) N3 0.098(4) 0.066(3) 0.097(4) 0.020(3) 0.077(3) 0.011(3) N4 0.254(16) 0.039(4) 0.309(19) 0.000 0.241(17) 0.000 C1 0.067(3) 0.070(3) 0.072(3) 0.011(3) 0.046(3) 0.004(3) C2 0.064(3) 0.061(3) 0.077(4) 0.001(3) 0.039(3) 0.009(3) C3 0.088(5) 0.082(4) 0.132(7) 0.007(4) 0.066(5) 0.032(4) C4 0.051(3) 0.057(3) 0.072(3) 0.002(2) 0.040(3) 0.005(2) C5 0.083(4) 0.063(3) 0.096(4) 0.008(3) 0.070(4) 0.010(3) C6 0.189(10) 0.107(6) 0.137(8) 0.052(6) 0.130(8) 0.032(7) C7 0.212(12) 0.099(6) 0.264(14) 0.099(8) 0.198(12) 0.066(7) C8 0.116(7) 0.057(4) 0.184(9) 0.027(5) 0.088(7) 0.006(4) C9 0.079(9) 0.099(11) 0.136(14) -0.062(10) 0.050(10) -0.050(9) P1 0.0745(11) 0.0908(12) 0.0941(12) 0.0324(10) 0.0563(10) 0.0247(9) F1 0.134(5) 0.138(5) 0.223(8) -0.035(5) 0.081(5) -0.017(4) F2 0.264(10) 0.096(4) 0.240(9) -0.005(5) 0.092(8) 0.007(6) F3 0.114(4) 0.320(10) 0.177(6) 0.162(7) 0.094(4) 0.117(6) F4 0.215(7) 0.226(7) 0.236(7) 0.143(6) 0.196(7) 0.140(6) F5 0.145(5) 0.183(6) 0.170(5) 0.065(5) 0.125(4) 0.053(4) F6 0.100(3) 0.152(4) 0.140(5) 0.073(4) 0.058(3) 0.039(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cu1 N3 1.968(5) . yes Cu1 N3 1.968(5) 2 yes Cu1 N4 1.984(8) . yes Cu1 N1 2.114(4) 2 yes Cu1 N1 2.114(4) . yes N2 C1 1.348(8) . ? N2 C2 1.367(8) . ? N1 C1 1.314(7) . ? N1 C4 1.400(6) . ? N3 C5 1.249(8) . ? N3 C6 1.486(8) . ? N4 C8 1.398(9) 2 ? N4 C8 1.398(9) . ? N4 C9 1.858(16) . ? N4 C9 1.858(15) 2 ? C2 C4 1.345(8) . ? C2 C3 1.497(8) . ? C4 C5 1.440(8) . ? C6 C7 1.352(13) . ? C7 C8 1.415(12) . ? P1 F2 1.532(8) . ? P1 F5 1.551(5) . ? P1 F4 1.564(5) . ? P1 F3 1.566(5) . ? P1 F1 1.571(7) . ? P1 F6 1.576(5) . ? 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 N3 Cu1 N3 175.5(3) . 2 yes N3 Cu1 N4 92.26(14) . . yes N3 Cu1 N4 92.26(14) 2 . yes N3 Cu1 N1 96.4(2) . 2 yes N3 Cu1 N1 80.57(19) 2 2 yes N4 Cu1 N1 132.00(12) . 2 yes N3 Cu1 N1 80.57(19) . . yes N3 Cu1 N1 96.4(2) 2 . yes N4 Cu1 N1 132.00(13) . . yes N1 Cu1 N1 96.0(2) 2 . yes C1 N2 C2 109.3(5) . . ? C1 N1 C4 105.1(4) . . ? C1 N1 Cu1 145.8(4) . . ? C4 N1 Cu1 108.1(3) . . ? C5 N3 C6 121.9(6) . . ? C5 N3 Cu1 117.2(4) . . ? C6 N3 Cu1 120.9(5) . . ? C8 N4 C8 123.2(9) 2 . ? C8 N4 C9 85.4(7) 2 . ? C8 N4 C9 90.2(7) . . ? C8 N4 C9 90.2(7) 2 2 ? C8 N4 C9 85.4(7) . 2 ? C9 N4 C9 170.8(12) . 2 ? C8 N4 Cu1 118.4(5) 2 . ? C8 N4 Cu1 118.4(5) . . ? C9 N4 Cu1 94.6(6) . . ? C9 N4 Cu1 94.6(6) 2 . ? N1 C1 N2 110.3(5) . . ? C4 C2 N2 104.8(5) . . ? C4 C2 C3 132.4(6) . . ? N2 C2 C3 122.8(6) . . ? C2 C4 N1 110.5(5) . . ? C2 C4 C5 133.9(5) . . ? N1 C4 C5 115.5(5) . . ? N3 C5 C4 118.4(5) . . ? C7 C6 N3 114.7(8) . . ? C6 C7 C8 129.3(7) . . ? N4 C8 C7 127.8(7) . . ? F2 P1 F5 90.1(5) . . ? F2 P1 F4 95.7(5) . . ? F5 P1 F4 174.2(5) . . ? F2 P1 F3 87.4(5) . . ? F5 P1 F3 91.5(3) . . ? F4 P1 F3 87.9(3) . . ? F2 P1 F1 177.0(5) . . ? F5 P1 F1 90.0(4) . . ? F4 P1 F1 84.2(5) . . ? F3 P1 F1 95.6(5) . . ? F2 P1 F6 92.0(5) . . ? F5 P1 F6 89.9(3) . . ? F4 P1 F6 90.7(3) . . ? F3 P1 F6 178.5(4) . . ? F1 P1 F6 84.9(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2B F4 0.86 2.15 3.006(7) 175.4 5_566 N2 H2B F6 0.86 2.38 2.969(7) 125.7 5_566 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.710 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.093 #============================================================END data_complex3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 Cl Cu N6 O6' _chemical_formula_weight 454.33 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' '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)/n' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 12.056(2) _cell_length_b 10.058(2) _cell_length_c 15.141(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.58(3) _cell_angle_gamma 90.00 _cell_volume 1835.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.644 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 932 _exptl_absorpt_coefficient_mu 1.380 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens CCD' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7962 _diffrn_reflns_av_R_equivalents 0.0557 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 23.33 _reflns_number_total 2644 _reflns_number_gt 2088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1990)' _computing_cell_refinement 'SHELXTL-Plus (Sheldrick, 1990)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_solution 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.5890P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2644 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.89600(3) 0.23763(4) 0.20103(3) 0.03545(18) Uani 1 1 d . . . N1 N 0.9067(2) 0.1715(3) 0.07357(18) 0.0378(7) Uani 1 1 d . . . N2 N 0.9138(3) 0.1039(3) -0.06438(19) 0.0464(8) Uani 1 1 d . . . H2A H 0.8959 0.0593 -0.1141 0.080 Uiso 1 1 d R . . N3 N 1.0314(2) 0.3421(3) 0.1619(2) 0.0419(7) Uani 1 1 d . . . N4 N 0.9536(2) 0.2471(3) 0.32721(19) 0.0379(7) Uani 1 1 d . . . N5 N 0.8053(2) 0.0895(3) 0.25055(18) 0.0359(7) Uani 1 1 d . . . N6 N 0.7131(2) -0.0896(3) 0.30110(18) 0.0390(7) Uani 1 1 d . . . C1 C 0.8612(3) 0.0943(4) 0.0136(2) 0.0423(9) Uani 1 1 d . . . H1A H 0.7982 0.0382 0.0238 0.080 Uiso 1 1 d R . . C2 C 0.9985(3) 0.1923(4) -0.0552(2) 0.0450(9) Uani 1 1 d . . . C3 C 1.0751(4) 0.2270(5) -0.1277(3) 0.0655(13) Uani 1 1 d . . . H3A H 1.0543 0.1790 -0.1802 0.080 Uiso 1 1 d R . . H3B H 1.0711 0.3208 -0.1391 0.080 Uiso 1 1 d R . . H3C H 1.1496 0.2036 -0.1109 0.080 Uiso 1 1 d R . . C4 C 0.9935(3) 0.2333(4) 0.0310(2) 0.0400(9) Uani 1 1 d . . . C5 C 1.0593(3) 0.3242(4) 0.0826(2) 0.0452(9) Uani 1 1 d . . . H5A H 1.1218 0.3694 0.0578 0.080 Uiso 1 1 d R . . C6 C 1.0949(3) 0.4328(4) 0.2177(2) 0.0540(11) Uani 1 1 d . . . H6A H 1.0513 0.5107 0.2290 0.080 Uiso 1 1 d R . . H6B H 1.1603 0.4602 0.1869 0.080 Uiso 1 1 d R . . C7 C 1.1287(3) 0.3703(4) 0.3050(2) 0.0473(10) Uani 1 1 d . . . H7A H 1.1773 0.4315 0.3349 0.080 Uiso 1 1 d R . . C8 C 1.0320(3) 0.3430(4) 0.3653(2) 0.0487(10) Uani 1 1 d . . . H8A H 1.0595 0.3092 0.4206 0.080 Uiso 1 1 d R . . H8B H 0.9939 0.4249 0.3768 0.080 Uiso 1 1 d R . . C9 C 0.9177(3) 0.1514(4) 0.3744(2) 0.0406(9) Uani 1 1 d . . . H9A H 0.9436 0.1396 0.4340 0.080 Uiso 1 1 d R . . C10 C 0.8389(3) 0.0633(3) 0.3366(2) 0.0372(8) Uani 1 1 d . . . C11 C 0.7826(3) -0.0453(4) 0.3667(2) 0.0407(9) Uani 1 1 d . . . C12 C 0.7902(4) -0.1103(4) 0.4555(3) 0.0615(12) Uani 1 1 d . . . H12A H 0.8436 -0.0642 0.4916 0.080 Uiso 1 1 d R . . H12B H 0.7190 -0.1071 0.4833 0.080 Uiso 1 1 d R . . H12C H 0.8126 -0.2013 0.4487 0.080 Uiso 1 1 d R . . C13 C 0.7312(3) -0.0049(3) 0.2338(2) 0.0392(9) Uani 1 1 d . . . H13A H 0.6934 -0.0124 0.1779 0.080 Uiso 1 1 d R . . O1 O 1.1869(2) 0.2482(3) 0.2945(2) 0.0633(8) Uani 1 1 d . . . H1B H 1.2418 0.2610 0.2607 0.080 Uiso 1 1 d R . . Cl1 Cl 1.38881(15) 0.23416(13) 0.10854(9) 0.0849(5) Uani 1 1 d . . . O2 O 1.3957(6) 0.3707(4) 0.0933(3) 0.157(2) Uani 1 1 d . . . O3 O 1.4882(5) 0.1735(5) 0.0848(3) 0.151(2) Uani 1 1 d . . . O4 O 1.3028(6) 0.1760(7) 0.0629(4) 0.186(3) Uani 1 1 d . . . O5 O 1.3788(4) 0.2169(4) 0.2011(2) 0.1084(15) Uani 1 1 d . . . O1W O 1.3885(3) 0.5087(3) 0.27221(18) 0.0724(9) Uani 1 1 d . . . H1WA H 1.3745 0.5956 0.2469 0.080 Uiso 1 1 d R . . H1WB H 1.4220 0.4710 0.2216 0.080 Uiso 1 1 d R . . 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 Cu1 0.0373(3) 0.0340(3) 0.0350(3) -0.00132(18) -0.00071(19) -0.00342(18) N1 0.0407(17) 0.0336(17) 0.0392(17) -0.0011(14) 0.0002(14) -0.0009(14) N2 0.058(2) 0.045(2) 0.0362(18) -0.0060(14) -0.0023(15) 0.0079(16) N3 0.0441(18) 0.0367(18) 0.0448(19) 0.0003(14) -0.0023(15) -0.0052(14) N4 0.0373(17) 0.0381(18) 0.0383(17) -0.0045(14) -0.0024(13) -0.0036(13) N5 0.0364(16) 0.0356(17) 0.0357(16) 0.0019(13) -0.0014(13) -0.0040(13) N6 0.0424(17) 0.0355(17) 0.0390(17) -0.0001(14) -0.0003(14) -0.0072(14) C1 0.047(2) 0.041(2) 0.039(2) -0.0014(17) -0.0003(18) 0.0011(17) C2 0.048(2) 0.044(2) 0.043(2) 0.0035(18) -0.0002(18) 0.0098(19) C3 0.071(3) 0.079(3) 0.046(2) 0.006(2) 0.016(2) 0.004(2) C4 0.040(2) 0.042(2) 0.039(2) 0.0007(17) 0.0026(17) 0.0042(17) C5 0.042(2) 0.044(2) 0.050(2) 0.0102(19) 0.0016(19) -0.0039(18) C6 0.058(3) 0.046(2) 0.058(3) -0.0018(19) -0.008(2) -0.019(2) C7 0.050(2) 0.040(2) 0.052(2) -0.0036(18) -0.0076(19) -0.0117(18) C8 0.051(2) 0.046(2) 0.049(2) -0.0083(18) -0.0060(19) -0.0150(19) C9 0.045(2) 0.041(2) 0.036(2) -0.0027(17) -0.0035(17) -0.0001(18) C10 0.039(2) 0.037(2) 0.0351(19) 0.0011(16) -0.0012(16) -0.0029(17) C11 0.044(2) 0.040(2) 0.038(2) -0.0005(16) -0.0028(17) -0.0027(17) C12 0.072(3) 0.059(3) 0.054(3) 0.013(2) -0.015(2) -0.024(2) C13 0.040(2) 0.043(2) 0.035(2) -0.0003(17) -0.0025(16) -0.0033(18) O1 0.0487(16) 0.067(2) 0.075(2) -0.0029(15) 0.0006(15) -0.0032(14) Cl1 0.1303(13) 0.0609(8) 0.0640(8) 0.0162(6) 0.0316(8) 0.0272(8) O2 0.334(7) 0.064(3) 0.075(3) 0.021(2) 0.050(3) 0.050(4) O3 0.181(5) 0.107(4) 0.168(5) 0.021(3) 0.101(4) 0.043(3) O4 0.203(6) 0.165(5) 0.188(6) -0.011(5) -0.099(5) 0.004(5) O5 0.141(4) 0.104(3) 0.081(3) 0.033(2) 0.039(3) 0.041(2) O1W 0.098(2) 0.065(2) 0.0544(17) 0.0205(15) 0.0150(16) 0.0110(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cu1 N5 1.998(3) . YES Cu1 N4 2.029(3) . YES Cu1 N3 2.034(3) . YES Cu1 N1 2.046(3) . YES Cu1 N6 2.180(3) 2_655 YES N1 C1 1.311(4) . ? N1 C4 1.382(4) . ? N2 C1 1.349(4) . ? N2 C2 1.360(5) . ? N2 O1W 2.735(4) 4_565 YES N3 C5 1.263(4) . ? N3 C6 1.456(4) . ? N4 C9 1.276(4) . ? N4 C8 1.464(4) . ? N5 C13 1.327(4) . ? N5 C10 1.386(4) . ? N6 C13 1.347(4) . ? N6 C11 1.368(4) . ? N6 Cu1 2.180(3) 2_645 ? C2 C4 1.371(5) . ? C2 C3 1.484(5) . ? C4 C5 1.436(5) . ? C6 C7 1.515(5) . ? C7 O1 1.425(5) . ? C7 C8 1.513(5) . ? C9 C10 1.416(5) . ? C10 C11 1.366(5) . ? C11 C12 1.497(5) . ? O1 O5 2.742(5) . ? Cl1 O4 1.372(6) . ? Cl1 O2 1.395(4) . ? Cl1 O3 1.395(5) . ? Cl1 O5 1.418(4) . ? O2 O1W 3.046(5) . ? O1W O1 2.762(4) 2_755 ? 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 N5 Cu1 N4 82.24(11) . . YES N5 Cu1 N3 159.69(12) . . YES N4 Cu1 N3 88.95(12) . . YES N5 Cu1 N1 98.72(11) . . YES N4 Cu1 N1 151.56(12) . . YES N3 Cu1 N1 80.50(12) . . YES N5 Cu1 N6 105.52(11) . 2_655 YES N4 Cu1 N6 100.20(11) . 2_655 YES N3 Cu1 N6 94.01(11) . 2_655 YES N1 Cu1 N6 106.79(11) . 2_655 YES C1 N1 C4 104.9(3) . . ? C1 N1 Cu1 144.7(2) . . ? C4 N1 Cu1 110.4(2) . . ? C1 N2 C2 108.5(3) . . ? C1 N2 O1W 135.4(3) . 4_565 YES C2 N2 O1W 116.1(2) . 4_565 YES C5 N3 C6 119.8(3) . . ? C5 N3 Cu1 115.2(2) . . ? C6 N3 Cu1 125.0(2) . . ? C9 N4 C8 119.8(3) . . ? C9 N4 Cu1 112.1(2) . . ? C8 N4 Cu1 128.0(2) . . ? C13 N5 C10 103.4(3) . . ? C13 N5 Cu1 146.3(2) . . ? C10 N5 Cu1 109.8(2) . . ? C13 N6 C11 103.9(3) . . ? C13 N6 Cu1 126.5(2) . 2_645 ? C11 N6 Cu1 129.5(2) . 2_645 ? N1 C1 N2 111.5(3) . . ? N2 C2 C4 104.7(3) . . ? N2 C2 C3 123.4(4) . . ? C4 C2 C3 131.9(4) . . ? C2 C4 N1 110.4(3) . . ? C2 C4 C5 132.9(4) . . ? N1 C4 C5 116.7(3) . . ? N3 C5 C4 117.2(3) . . ? N3 C6 C7 112.4(3) . . ? O1 C7 C8 107.1(3) . . ? O1 C7 C6 112.9(3) . . ? C8 C7 C6 113.6(3) . . ? N4 C8 C7 112.4(3) . . ? N4 C9 C10 118.4(3) . . ? C11 C10 N5 108.9(3) . . ? C11 C10 C9 134.4(3) . . ? N5 C10 C9 116.6(3) . . ? C10 C11 N6 108.7(3) . . ? C10 C11 C12 128.5(3) . . ? N6 C11 C12 122.8(3) . . ? N5 C13 N6 115.0(3) . . ? C7 O1 O5 125.1(2) . . ? O4 Cl1 O2 112.5(4) . . ? O4 Cl1 O3 109.3(4) . . ? O2 Cl1 O3 109.6(3) . . ? O4 Cl1 O5 112.0(4) . . ? O2 Cl1 O5 106.9(3) . . ? O3 Cl1 O5 106.4(3) . . ? Cl1 O2 O1W 107.4(2) . . ? Cl1 O5 O1 125.2(2) . . ? O1 O1W O2 94.85(13) 2_755 . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 23.33 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.408 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.060 End #=========================================================# data_complex4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 Cl Cu N6 O6' _chemical_formula_weight 454.33 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' '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.620(2) _cell_length_b 10.045(2) _cell_length_c 9.699(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.87(3) _cell_angle_gamma 90.00 _cell_volume 913.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7.5 _cell_measurement_theta_max 15 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.651 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 466 _exptl_absorpt_coefficient_mu 1.386 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens CAD4' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 120 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 1822 _diffrn_reflns_av_R_equivalents 0.1107 _diffrn_reflns_av_sigmaI/netI 0.0932 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.96 _reflns_number_total 1742 _reflns_number_gt 1111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SHELXTL-Plus (Sheldrick, 1990)' _computing_cell_refinement 'SHELXTL-Plus (Sheldrick, 1990)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_solution 'SHELXTL-Plus (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V.5.0 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1390P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(8) _refine_ls_number_reflns 1742 _refine_ls_number_parameters 244 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1228 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2135 _refine_ls_wR_factor_gt 0.1836 _refine_ls_goodness_of_fit_ref 0.961 _refine_ls_restrained_S_all 1.011 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.09686(15) 0.0232(3) 0.69487(14) 0.0385(5) Uani 1 1 d . . . N1 N -0.0179(14) 0.1063(14) 0.8343(13) 0.045(3) Uani 1 1 d . . . N2 N -0.1519(14) 0.1731(16) 0.9791(15) 0.052(3) Uani 1 1 d . . . H2A H -0.2182 0.2190 1.0118 0.080 Uiso 1 1 d R . . N3 N 0.1943(14) -0.0720(15) 0.8707(14) 0.047(3) Uani 1 1 d D . . N4 N 0.2829(9) 0.0195(17) 0.6261(9) 0.033(2) Uani 1 1 d D . . N5 N 0.0586(17) 0.189(2) 0.5480(19) 0.060(4) Uani 1 1 d . . . N6 N 0.0066(17) 0.3625(14) 0.4126(12) 0.047(4) Uani 1 1 d . . . C1 C -0.1239(17) 0.1805(18) 0.8456(16) 0.047(4) Uani 1 1 d . . . H1A H -0.1771 0.2348 0.7707 0.080 Uiso 1 1 d R . . C2 C -0.0536(17) 0.0762(18) 1.0549(18) 0.052(4) Uani 1 1 d . . . C3 C -0.053(2) 0.042(4) 1.2003(16) 0.074(6) Uani 1 1 d . . . H3A H 0.0190 -0.0241 1.2341 0.080 Uiso 1 1 d R . . H3B H -0.0329 0.1204 1.2575 0.080 Uiso 1 1 d R . . H3C H -0.1446 0.0072 1.2059 0.080 Uiso 1 1 d R . . C4 C 0.0262(14) 0.031(4) 0.9648(11) 0.049(3) Uani 1 1 d . . . C5 C 0.1412(19) -0.0445(17) 0.9762(14) 0.048(4) Uani 1 1 d . . . H5A H 0.1862 -0.0807 1.0667 0.080 Uiso 1 1 d R . . C6 C 0.310(2) -0.160(2) 0.874(3) 0.18(3) Uani 1 1 d D . . H6A H 0.2781 -0.2327 0.8104 0.080 Uiso 1 1 d R . . H6B H 0.3495 -0.1920 0.9676 0.080 Uiso 1 1 d R . . C7 C 0.4306(15) -0.0951(17) 0.8214(15) 0.053(4) Uani 1 1 d D . . H7A H 0.5176 -0.1450 0.8325 0.080 Uiso 1 1 d R . . C8 C 0.3980(15) -0.0682(14) 0.6659(14) 0.043(3) Uani 1 1 d D . . H8A H 0.4801 -0.0307 0.6394 0.080 Uiso 1 1 d R . . H8B H 0.3756 -0.1504 0.6154 0.080 Uiso 1 1 d R . . C9 C 0.2911(17) 0.1237(15) 0.5454(16) 0.043(3) Uani 1 1 d . . . H9A H 0.3781 0.1392 0.5150 0.080 Uiso 1 1 d R . . C10 C 0.1729(14) 0.2145(17) 0.5025(13) 0.039(3) Uani 1 1 d . . . C11 C 0.1476(16) 0.3253(19) 0.412(2) 0.053(4) Uani 1 1 d . . . C12 C 0.246(2) 0.390(2) 0.333(2) 0.068(5) Uani 1 1 d . . . H12A H 0.3346 0.3427 0.3519 0.080 Uiso 1 1 d R . . H12B H 0.2042 0.3878 0.2334 0.080 Uiso 1 1 d R . . H12C H 0.2617 0.4805 0.3637 0.080 Uiso 1 1 d R . . C13 C -0.031(2) 0.282(2) 0.499(2) 0.049(6) Uani 1 1 d . . . H13A H -0.1217 0.2908 0.5245 0.080 Uiso 1 1 d R . . O1 O 0.4777(12) 0.025(2) 0.8953(10) 0.062(3) Uani 1 1 d . . . H1B H 0.5306 0.0690 0.8522 0.080 Uiso 1 1 d R . . O1W O 0.329(2) 0.251(3) 0.878(2) 0.098(7) Uani 1 1 d . . . H1WA H 0.3433 0.1626 0.8724 0.080 Uiso 1 1 d R . . H1WB H 0.4073 0.2744 0.7954 0.080 Uiso 1 1 d R . . Cl1 Cl 0.4978(6) 0.5182(9) 0.7165(5) 0.0872(15) Uani 1 1 d D . . O2 O 0.4148(16) 0.506(3) 0.8181(13) 0.141(11) Uani 1 1 d D . . O3 O 0.519(3) 0.6524(11) 0.693(3) 0.23(3) Uani 1 1 d D . . O4 O 0.6283(17) 0.4501(19) 0.761(3) 0.163(11) Uani 1 1 d D . . O5 O 0.424(2) 0.454(2) 0.5917(14) 0.142(10) Uani 1 1 d 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 Cu1 0.0303(7) 0.0463(9) 0.0370(7) 0.0009(14) 0.0033(5) 0.0010(14) N1 0.049(8) 0.044(8) 0.040(6) 0.004(5) 0.009(5) 0.011(6) N2 0.039(7) 0.052(8) 0.065(9) -0.018(7) 0.014(6) -0.003(6) N3 0.028(6) 0.062(9) 0.052(8) 0.016(7) 0.007(5) 0.010(6) N4 0.035(5) 0.029(5) 0.033(4) -0.008(8) 0.005(3) -0.011(9) N5 0.047(9) 0.070(11) 0.065(10) -0.031(9) 0.017(7) 0.006(8) N6 0.067(10) 0.033(7) 0.025(6) 0.010(5) -0.021(6) 0.007(7) C1 0.048(9) 0.046(9) 0.042(8) -0.004(7) 0.001(6) -0.010(8) C2 0.041(8) 0.050(10) 0.065(10) -0.001(7) 0.012(7) -0.003(7) C3 0.078(11) 0.095(19) 0.047(8) -0.013(14) 0.011(7) 0.000(17) C4 0.048(7) 0.067(10) 0.030(5) 0.004(13) 0.003(5) -0.004(15) C5 0.071(11) 0.049(9) 0.020(6) 0.004(6) -0.001(6) 0.001(9) C6 0.14(4) 0.35(8) 0.057(18) 0.00(3) 0.04(2) -0.17(5) C7 0.043(9) 0.035(9) 0.079(12) -0.002(8) 0.011(8) 0.002(7) C8 0.047(8) 0.024(7) 0.059(9) -0.001(7) 0.013(7) 0.008(6) C9 0.045(8) 0.031(8) 0.055(8) -0.005(7) 0.016(6) 0.015(7) C10 0.026(7) 0.058(10) 0.031(6) 0.012(6) 0.005(5) 0.007(7) C11 0.030(7) 0.052(10) 0.075(11) 0.025(9) 0.007(7) 0.010(7) C12 0.083(14) 0.072(13) 0.057(10) 0.009(9) 0.033(9) 0.019(11) C13 0.075(18) 0.036(9) 0.032(6) 0.006(6) 0.004(10) 0.028(11) O1 0.071(7) 0.058(7) 0.052(5) -0.005(9) -0.001(4) -0.044(10) O1W 0.096(15) 0.141(17) 0.057(11) -0.017(10) 0.016(10) 0.033(13) Cl1 0.119(4) 0.079(3) 0.074(3) 0.000(5) 0.042(3) 0.009(6) O2 0.120(12) 0.25(3) 0.061(8) 0.013(17) 0.026(8) -0.07(2) O3 0.46(7) 0.045(12) 0.28(4) 0.044(17) 0.28(5) 0.02(2) O4 0.20(3) 0.068(13) 0.24(3) -0.024(17) 0.08(2) 0.031(17) O5 0.22(3) 0.120(18) 0.076(12) -0.011(11) 0.025(14) -0.047(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cu1 N3 1.997(12) . YES Cu1 N4 2.045(9) . YES Cu1 N6 2.055(13) 2_546 YES Cu1 N1 2.099(13) . YES Cu1 N5 2.16(2) . YES N1 C1 1.29(2) . ? N1 C4 1.46(2) . ? N2 C1 1.38(2) . ? N2 C2 1.44(2) . ? N2 N3 3.02(2) 2_557 YES N3 C5 1.27(2) . ? N3 C6 1.416(11) . ? N4 C9 1.32(2) . ? N4 C8 1.400(10) . ? N5 C13 1.30(3) . ? N5 C10 1.30(2) . ? N6 C13 1.27(3) . ? N6 C11 1.41(2) . ? N6 Cu1 2.055(13) 2_556 YES C2 C4 1.36(2) . ? C2 C3 1.45(2) . ? C4 C5 1.32(3) . ? C6 C7 1.514(10) . ? C7 O1 1.43(2) . ? C7 C8 1.495(10) . ? C9 C10 1.44(2) . ? C10 C11 1.41(2) . ? C11 C12 1.49(2) . ? O1 O1W 2.67(3) . YES O1 O2 2.748(17) 2_647 YES Cl1 O3 1.390(9) . ? Cl1 O2 1.405(8) . ? Cl1 O4 1.411(10) . ? Cl1 O5 1.412(9) . ? 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 N3 Cu1 N4 89.5(5) . . YES N3 Cu1 N6 98.0(6) . 2_546 YES N4 Cu1 N6 100.4(6) . 2_546 YES N3 Cu1 N1 81.6(5) . . YES N4 Cu1 N1 147.3(6) . . YES N6 Cu1 N1 112.0(6) 2_546 . YES N3 Cu1 N5 155.2(6) . . YES N4 Cu1 N5 80.4(6) . . YES N6 Cu1 N5 106.1(5) 2_546 . YES N1 Cu1 N5 94.7(5) . . YES C1 N1 C4 108.1(14) . . ? C1 N1 Cu1 145.6(10) . . ? C4 N1 Cu1 105.0(12) . . ? C1 N2 C2 105.8(14) . . ? C1 N2 N3 118.8(12) . 2_557 ? C2 N2 N3 118.1(10) . 2_557 ? C5 N3 C6 125.0(15) . . ? C5 N3 Cu1 112.7(11) . . ? C6 N3 Cu1 122.3(13) . . ? C9 N4 C8 121.0(11) . . ? C9 N4 Cu1 110.5(10) . . ? C8 N4 Cu1 128.1(10) . . ? C13 N5 C10 106(2) . . ? C13 N5 Cu1 143.3(15) . . ? C10 N5 Cu1 110.2(13) . . ? C13 N6 C11 104.8(13) . . ? C13 N6 Cu1 130.8(13) . 2_556 ? C11 N6 Cu1 124.2(12) . 2_556 ? N1 C1 N2 111.8(14) . . ? C4 C2 N2 107.4(16) . . ? C4 C2 C3 131(2) . . ? N2 C2 C3 121.2(18) . . ? C5 C4 C2 135.8(14) . . ? C5 C4 N1 116.5(12) . . ? C2 C4 N1 107(2) . . ? N3 C5 C4 122.3(13) . . ? N3 C6 C7 112.5(15) . . ? O1 C7 C8 109.0(13) . . ? O1 C7 C6 112.2(17) . . ? C8 C7 C6 114.3(13) . . ? N4 C8 C7 111.5(11) . . ? N4 C9 C10 121.7(14) . . ? N5 C10 C11 109.3(15) . . ? N5 C10 C9 116.5(16) . . ? C11 C10 C9 134.0(14) . . ? C10 C11 N6 103.7(14) . . ? C10 C11 C12 128.7(14) . . ? N6 C11 C12 127.6(15) . . ? N6 C13 N5 115.9(16) . . ? C7 O1 O1W 125.8(10) . . ? C7 O1 O2 117.0(13) . 2_647 ? O1W O1 O2 101.4(9) . 2_647 ? O3 Cl1 O2 108.9(13) . . ? O3 Cl1 O4 111.5(14) . . ? O2 Cl1 O4 110.3(12) . . ? O3 Cl1 O5 111.5(13) . . ? O2 Cl1 O5 107.9(11) . . ? O4 Cl1 O5 106.6(12) . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25.96 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.656 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.128