Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Steve Archibald' _publ_contact_author_address ; Department of Chemistry University of Hull Cottingham Road Kingston upon Hull HU16 7RX UNITED KINGDOM ; _publ_contact_author_email S.J.ARCHIBALD@HULL.AC.UK _publ_section_title ; Copper(II) cyclam based complexes for radiopharmaceutical applications: synthesis and structural analysis ; loop_ _publ_author_name S.Archibald C.C.Allan J.D.Silversides data_sja18_04 _database_code_depnum_ccdc_archive 'CCDC 624741' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H36 Cl3 Cu2 N4 O2' _chemical_formula_sum 'C18 H36 Cl3 Cu2 N4 O2' _chemical_formula_weight 573.94 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' 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 8.3937(16) _cell_length_b 27.970(6) _cell_length_c 10.273(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.069(15) _cell_angle_gamma 90.00 _cell_volume 2358.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 2.165 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe IPDSII image plate' _diffrn_measurement_method '149 frames at 2^o intervals, exposure time 6 minutes' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23231 _diffrn_reflns_av_R_equivalents 0.1083 _diffrn_reflns_av_sigmaI/netI 0.1161 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -42 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 32.50 _reflns_number_total 7665 _reflns_number_gt 4282 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-AREA _computing_cell_refinement X-AREA _computing_data_reduction X-RED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _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^)+(0.1089P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0031(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.35(3) _refine_ls_number_reflns 7665 _refine_ls_number_parameters 263 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1278 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.1982 _refine_ls_wR_factor_gt 0.1662 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.933 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 0.32779(9) 0.14596(3) 1.02160(8) 0.02718(19) Uani 1 1 d . . . Cu2 Cu 0.46686(12) 0.13965(3) 1.42953(9) 0.0388(3) Uani 1 1 d . . . Cl1 Cl 0.6052(3) 0.15842(6) 1.2633(2) 0.0379(4) Uani 1 1 d . . . Cl2 Cl 0.3433(3) 0.19608(7) 1.5222(2) 0.0395(4) Uani 1 1 d . . . Cl3 Cl 0.4354(3) 0.06083(7) 1.4475(2) 0.0488(6) Uani 1 1 d . . . O1 O 0.1317(7) 0.11156(19) 0.8401(6) 0.0364(12) Uani 1 1 d . . . O2 O 0.1305(7) 0.05897(19) 0.6731(5) 0.0357(12) Uani 1 1 d . . . N1 N 0.4062(8) 0.2072(2) 0.9574(7) 0.0314(13) Uani 1 1 d . . . N2 N 0.4635(9) 0.0958(2) 0.9451(7) 0.0322(13) Uani 1 1 d . . . N3 N 0.2696(9) 0.0942(2) 1.1346(7) 0.0332(13) Uani 1 1 d . . . H3 H 0.3332 0.0995 1.2190 0.040 Uiso 1 1 calc R . . N4 N 0.1575(8) 0.1951(2) 1.0406(6) 0.0294(12) Uani 1 1 d . . . C1 C 0.5655(11) 0.2076(3) 0.9162(8) 0.0381(17) Uani 1 1 d . . . H1A H 0.6532 0.2124 0.9960 0.046 Uiso 1 1 calc R . . H1B H 0.5680 0.2351 0.8559 0.046 Uiso 1 1 calc R . . C2 C 0.6002(11) 0.1616(3) 0.8455(9) 0.0425(18) Uani 1 1 d . . . H2A H 0.5093 0.1562 0.7684 0.051 Uiso 1 1 calc R . . H2B H 0.7002 0.1665 0.8104 0.051 Uiso 1 1 calc R . . C3 C 0.6216(10) 0.1178(3) 0.9290(8) 0.0358(16) Uani 1 1 d . . . H3A H 0.6872 0.1258 1.0181 0.043 Uiso 1 1 calc R . . H3B H 0.6835 0.0939 0.8883 0.043 Uiso 1 1 calc R . . C4 C 0.4882(11) 0.0589(3) 1.0509(9) 0.0427(19) Uani 1 1 d . . . H4A H 0.5689 0.0703 1.1293 0.051 Uiso 1 1 calc R . . H4B H 0.5304 0.0292 1.0181 0.051 Uiso 1 1 calc R . . C5 C 0.3292(11) 0.0492(3) 1.0893(9) 0.0407(19) Uani 1 1 d . . . H5A H 0.2496 0.0365 1.0120 0.049 Uiso 1 1 calc R . . H5B H 0.3438 0.0251 1.1615 0.049 Uiso 1 1 calc R . . C6 C 0.1006(11) 0.0935(3) 1.1526(9) 0.0405(18) Uani 1 1 d . . . H6A H 0.0891 0.0686 1.2186 0.049 Uiso 1 1 calc R . . H6B H 0.0271 0.0851 1.0672 0.049 Uiso 1 1 calc R . . C7 C 0.0507(11) 0.1419(3) 1.2001(8) 0.0394(17) Uani 1 1 d . . . H7A H -0.0470 0.1375 1.2388 0.047 Uiso 1 1 calc R . . H7B H 0.1396 0.1539 1.2716 0.047 Uiso 1 1 calc R . . C8 C 0.0135(10) 0.1791(3) 1.0909(7) 0.0345(15) Uani 1 1 d . . . H8A H -0.0676 0.1657 1.0157 0.041 Uiso 1 1 calc R . . H8B H -0.0365 0.2072 1.1250 0.041 Uiso 1 1 calc R . . C9 C 0.1116(10) 0.2159(3) 0.9035(7) 0.0328(15) Uani 1 1 d . . . H9A H 0.0636 0.2480 0.9075 0.039 Uiso 1 1 calc R . . H9B H 0.0296 0.1953 0.8464 0.039 Uiso 1 1 calc R . . C10 C 0.2647(9) 0.2194(3) 0.8451(7) 0.0331(15) Uani 1 1 d . . . H10A H 0.2586 0.1966 0.7705 0.040 Uiso 1 1 calc R . . H10B H 0.2770 0.2521 0.8118 0.040 Uiso 1 1 calc R . . C11 C 0.4001(12) 0.2426(2) 1.0614(9) 0.0421(19) Uani 1 1 d . . . H11A H 0.3895 0.2751 1.0224 0.050 Uiso 1 1 calc R . . H11B H 0.5018 0.2413 1.1304 0.050 Uiso 1 1 calc R . . C12 C 0.2559(10) 0.2319(3) 1.1229(7) 0.0338(15) Uani 1 1 d . . . H12A H 0.2934 0.2202 1.2152 0.041 Uiso 1 1 calc R . . H12B H 0.1903 0.2612 1.1253 0.041 Uiso 1 1 calc R . . C13 C 0.3804(11) 0.0738(3) 0.8183(9) 0.044(2) Uani 1 1 d . . . H13A H 0.3964 0.0388 0.8252 0.053 Uiso 1 1 calc R . . H13B H 0.4334 0.0854 0.7467 0.053 Uiso 1 1 calc R . . C14 C 0.1988(10) 0.0840(2) 0.7783(7) 0.0334(15) Uani 1 1 d . . . C15 C -0.0428(9) 0.0678(3) 0.6030(7) 0.0315(14) Uani 1 1 d . . . C16 C -0.0583(12) 0.0374(4) 0.4788(8) 0.045(2) Uani 1 1 d . . . H16A H -0.0442 0.0036 0.5041 0.068 Uiso 1 1 calc R . . H16B H 0.0255 0.0468 0.4302 0.068 Uiso 1 1 calc R . . H16C H -0.1664 0.0421 0.4218 0.068 Uiso 1 1 calc R . . C17 C -0.0643(14) 0.1198(3) 0.5686(11) 0.056(3) Uani 1 1 d . . . H17A H 0.0102 0.1289 0.5109 0.083 Uiso 1 1 calc R . . H17B H -0.0403 0.1389 0.6503 0.083 Uiso 1 1 calc R . . H17C H -0.1769 0.1256 0.5219 0.083 Uiso 1 1 calc R . . C18 C -0.1510(13) 0.0495(4) 0.6908(10) 0.053(2) Uani 1 1 d . . . H18A H -0.1296 0.0155 0.7086 0.080 Uiso 1 1 calc R . . H18B H -0.2652 0.0540 0.6463 0.080 Uiso 1 1 calc R . . H18C H -0.1289 0.0672 0.7750 0.080 Uiso 1 1 calc 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 0.0285(4) 0.0223(3) 0.0319(4) 0.0013(3) 0.0087(3) 0.0013(3) Cu2 0.0403(6) 0.0389(5) 0.0338(5) -0.0024(4) -0.0002(4) 0.0037(4) Cl1 0.0426(11) 0.0352(8) 0.0367(9) -0.0024(6) 0.0105(7) -0.0044(7) Cl2 0.0439(12) 0.0414(8) 0.0345(8) -0.0026(8) 0.0112(7) 0.0037(9) Cl3 0.0610(15) 0.0329(8) 0.0495(12) 0.0092(8) 0.0046(10) -0.0018(8) O1 0.032(3) 0.039(3) 0.037(3) -0.007(2) 0.003(2) 0.008(2) O2 0.031(3) 0.039(3) 0.034(3) -0.009(2) 0.000(2) 0.003(2) N1 0.033(3) 0.024(2) 0.038(3) 0.005(2) 0.007(3) -0.004(2) N2 0.031(3) 0.028(3) 0.038(3) -0.010(2) 0.007(2) 0.005(2) N3 0.035(3) 0.025(3) 0.038(3) 0.007(2) 0.004(3) -0.009(2) N4 0.027(3) 0.028(2) 0.032(3) -0.001(2) 0.003(2) 0.004(2) C1 0.039(4) 0.035(3) 0.040(4) 0.011(3) 0.008(3) -0.001(3) C2 0.033(4) 0.058(5) 0.040(4) 0.006(4) 0.017(3) 0.005(4) C3 0.029(4) 0.048(4) 0.030(3) -0.007(3) 0.004(3) 0.005(3) C4 0.041(5) 0.028(3) 0.054(5) -0.004(3) -0.002(4) 0.009(3) C5 0.040(4) 0.024(3) 0.055(5) 0.000(3) 0.001(4) -0.002(3) C6 0.040(5) 0.044(4) 0.037(4) 0.007(3) 0.008(3) -0.010(3) C7 0.030(4) 0.057(5) 0.032(4) 0.005(3) 0.011(3) 0.000(3) C8 0.030(4) 0.044(4) 0.030(3) -0.002(3) 0.006(3) 0.005(3) C9 0.035(4) 0.032(3) 0.030(3) 0.004(2) 0.003(3) 0.006(3) C10 0.032(4) 0.038(3) 0.028(3) 0.005(3) 0.003(3) 0.004(3) C11 0.051(5) 0.022(3) 0.052(5) 0.002(3) 0.008(4) -0.006(3) C12 0.037(4) 0.034(3) 0.029(3) -0.002(3) 0.003(3) 0.003(3) C13 0.035(4) 0.052(5) 0.044(4) -0.018(4) 0.003(3) 0.004(3) C14 0.043(4) 0.030(3) 0.028(3) -0.008(2) 0.010(3) 0.000(3) C15 0.029(4) 0.037(3) 0.025(3) 0.001(2) -0.002(3) 0.001(3) C16 0.043(5) 0.064(5) 0.028(4) -0.014(3) 0.005(3) 0.002(4) C17 0.056(6) 0.043(4) 0.057(6) 0.004(4) -0.013(5) 0.001(4) C18 0.046(5) 0.074(6) 0.038(5) -0.004(4) 0.003(4) -0.010(5) _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 1.980(6) . ? Cu1 N1 1.995(6) . ? Cu1 N4 2.021(6) . ? Cu1 N2 2.063(6) . ? Cu1 O1 2.414(5) . ? Cu2 Cl2 2.210(2) . ? Cu2 Cl3 2.233(2) . ? Cu2 Cl1 2.317(2) . ? O1 C14 1.210(9) . ? O2 C14 1.315(8) . ? O2 C15 1.502(9) . ? N1 C11 1.467(11) . ? N1 C1 1.484(11) . ? N1 C10 1.512(9) . ? N2 C13 1.477(10) . ? N2 C4 1.482(11) . ? N2 C3 1.504(11) . ? N3 C5 1.466(10) . ? N3 C6 1.468(12) . ? N3 H3 0.9300 . ? N4 C12 1.473(9) . ? N4 C8 1.479(10) . ? N4 C9 1.498(9) . ? C1 C2 1.535(12) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.485(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.494(14) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.529(13) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.513(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.531(11) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.507(13) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.521(12) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C15 C18 1.497(13) . ? C15 C17 1.499(11) . ? C15 C16 1.516(10) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 N1 163.8(3) . . ? N3 Cu1 N4 100.0(3) . . ? N1 Cu1 N4 74.8(3) . . ? N3 Cu1 N2 87.1(3) . . ? N1 Cu1 N2 102.2(3) . . ? N4 Cu1 N2 163.1(3) . . ? N3 Cu1 O1 87.1(2) . . ? N1 Cu1 O1 107.8(2) . . ? N4 Cu1 O1 87.9(2) . . ? N2 Cu1 O1 77.1(2) . . ? Cl2 Cu2 Cl3 126.53(11) . . ? Cl2 Cu2 Cl1 120.53(9) . . ? Cl3 Cu2 Cl1 111.77(9) . . ? C14 O1 Cu1 110.0(5) . . ? C14 O2 C15 121.3(6) . . ? C11 N1 C1 111.9(7) . . ? C11 N1 C10 105.1(6) . . ? C1 N1 C10 113.0(6) . . ? C11 N1 Cu1 106.0(5) . . ? C1 N1 Cu1 118.8(5) . . ? C10 N1 Cu1 100.7(4) . . ? C13 N2 C4 108.9(6) . . ? C13 N2 C3 109.7(7) . . ? C4 N2 C3 112.0(6) . . ? C13 N2 Cu1 115.0(5) . . ? C4 N2 Cu1 101.4(5) . . ? C3 N2 Cu1 109.5(4) . . ? C5 N3 C6 115.5(6) . . ? C5 N3 Cu1 107.4(6) . . ? C6 N3 Cu1 116.6(5) . . ? C5 N3 H3 105.4 . . ? C6 N3 H3 105.4 . . ? Cu1 N3 H3 105.4 . . ? C12 N4 C8 114.4(6) . . ? C12 N4 C9 105.7(5) . . ? C8 N4 C9 112.2(6) . . ? C12 N4 Cu1 102.0(4) . . ? C8 N4 Cu1 118.3(4) . . ? C9 N4 Cu1 102.8(4) . . ? N1 C1 C2 113.5(7) . . ? N1 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N1 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 115.5(7) . . ? C3 C2 H2A 108.4 . . ? C1 C2 H2A 108.4 . . ? C3 C2 H2B 108.4 . . ? C1 C2 H2B 108.4 . . ? H2A C2 H2B 107.5 . . ? C2 C3 N2 113.5(7) . . ? C2 C3 H3A 108.9 . . ? N2 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? N2 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? N2 C4 C5 108.9(6) . . ? N2 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? N2 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N3 C5 C4 108.1(6) . . ? N3 C5 H5A 110.1 . . ? C4 C5 H5A 110.1 . . ? N3 C5 H5B 110.1 . . ? C4 C5 H5B 110.1 . . ? H5A C5 H5B 108.4 . . ? N3 C6 C7 111.4(6) . . ? N3 C6 H6A 109.4 . . ? C7 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C7 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C6 113.6(7) . . ? C8 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C6 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? N4 C8 C7 114.2(6) . . ? N4 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? N4 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? N4 C9 C10 108.7(6) . . ? N4 C9 H9A 109.9 . . ? C10 C9 H9A 109.9 . . ? N4 C9 H9B 109.9 . . ? C10 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N1 C10 C9 106.0(6) . . ? N1 C10 H10A 110.5 . . ? C9 C10 H10A 110.5 . . ? N1 C10 H10B 110.5 . . ? C9 C10 H10B 110.5 . . ? H10A C10 H10B 108.7 . . ? N1 C11 C12 108.9(6) . . ? N1 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? N1 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? N4 C12 C11 107.6(6) . . ? N4 C12 H12A 110.2 . . ? C11 C12 H12A 110.2 . . ? N4 C12 H12B 110.2 . . ? C11 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? N2 C13 C14 114.9(7) . . ? N2 C13 H13A 108.5 . . ? C14 C13 H13A 108.5 . . ? N2 C13 H13B 108.5 . . ? C14 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? O1 C14 O2 126.8(8) . . ? O1 C14 C13 121.9(7) . . ? O2 C14 C13 111.3(6) . . ? C18 C15 C17 114.5(9) . . ? C18 C15 O2 107.7(6) . . ? C17 C15 O2 109.2(6) . . ? C18 C15 C16 111.1(7) . . ? C17 C15 C16 111.2(7) . . ? O2 C15 C16 102.5(6) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 Cu1 O1 C14 -93.6(6) . . . . ? N1 Cu1 O1 C14 92.9(6) . . . . ? N4 Cu1 O1 C14 166.2(6) . . . . ? N2 Cu1 O1 C14 -5.9(6) . . . . ? N3 Cu1 N1 C11 -22.8(13) . . . . ? N4 Cu1 N1 C11 50.4(5) . . . . ? N2 Cu1 N1 C11 -146.7(5) . . . . ? O1 Cu1 N1 C11 133.1(5) . . . . ? N3 Cu1 N1 C1 104.0(11) . . . . ? N4 Cu1 N1 C1 177.2(6) . . . . ? N2 Cu1 N1 C1 -19.9(6) . . . . ? O1 Cu1 N1 C1 -100.1(5) . . . . ? N3 Cu1 N1 C10 -132.1(10) . . . . ? N4 Cu1 N1 C10 -58.9(5) . . . . ? N2 Cu1 N1 C10 104.0(5) . . . . ? O1 Cu1 N1 C10 23.8(5) . . . . ? N3 Cu1 N2 C13 96.7(7) . . . . ? N1 Cu1 N2 C13 -96.7(6) . . . . ? N4 Cu1 N2 C13 -19.0(13) . . . . ? O1 Cu1 N2 C13 9.0(6) . . . . ? N3 Cu1 N2 C4 -20.7(5) . . . . ? N1 Cu1 N2 C4 145.9(5) . . . . ? N4 Cu1 N2 C4 -136.4(9) . . . . ? O1 Cu1 N2 C4 -108.4(5) . . . . ? N3 Cu1 N2 C3 -139.2(5) . . . . ? N1 Cu1 N2 C3 27.4(6) . . . . ? N4 Cu1 N2 C3 105.1(10) . . . . ? O1 Cu1 N2 C3 133.1(5) . . . . ? N1 Cu1 N3 C5 -134.4(10) . . . . ? N4 Cu1 N3 C5 155.8(5) . . . . ? N2 Cu1 N3 C5 -8.7(5) . . . . ? O1 Cu1 N3 C5 68.5(5) . . . . ? N1 Cu1 N3 C6 94.2(11) . . . . ? N4 Cu1 N3 C6 24.4(6) . . . . ? N2 Cu1 N3 C6 -140.1(6) . . . . ? O1 Cu1 N3 C6 -62.9(6) . . . . ? N3 Cu1 N4 C12 109.2(5) . . . . ? N1 Cu1 N4 C12 -55.1(5) . . . . ? N2 Cu1 N4 C12 -136.9(9) . . . . ? O1 Cu1 N4 C12 -164.1(5) . . . . ? N3 Cu1 N4 C8 -17.2(5) . . . . ? N1 Cu1 N4 C8 178.6(5) . . . . ? N2 Cu1 N4 C8 96.8(10) . . . . ? O1 Cu1 N4 C8 69.5(5) . . . . ? N3 Cu1 N4 C9 -141.4(4) . . . . ? N1 Cu1 N4 C9 54.3(4) . . . . ? N2 Cu1 N4 C9 -27.5(11) . . . . ? O1 Cu1 N4 C9 -54.7(4) . . . . ? C11 N1 C1 C2 160.5(7) . . . . ? C10 N1 C1 C2 -81.0(8) . . . . ? Cu1 N1 C1 C2 36.5(8) . . . . ? N1 C1 C2 C3 -66.0(9) . . . . ? C1 C2 C3 N2 80.2(9) . . . . ? C13 N2 C3 C2 71.2(8) . . . . ? C4 N2 C3 C2 -167.7(7) . . . . ? Cu1 N2 C3 C2 -55.9(8) . . . . ? C13 N2 C4 C5 -75.0(8) . . . . ? C3 N2 C4 C5 163.4(6) . . . . ? Cu1 N2 C4 C5 46.7(7) . . . . ? C6 N3 C5 C4 169.0(7) . . . . ? Cu1 N3 C5 C4 37.0(7) . . . . ? N2 C4 C5 N3 -58.4(8) . . . . ? C5 N3 C6 C7 179.9(7) . . . . ? Cu1 N3 C6 C7 -52.5(8) . . . . ? N3 C6 C7 C8 76.8(9) . . . . ? C12 N4 C8 C7 -81.8(8) . . . . ? C9 N4 C8 C7 157.8(6) . . . . ? Cu1 N4 C8 C7 38.4(8) . . . . ? C6 C7 C8 N4 -68.5(9) . . . . ? C12 N4 C9 C10 69.3(7) . . . . ? C8 N4 C9 C10 -165.4(6) . . . . ? Cu1 N4 C9 C10 -37.3(6) . . . . ? C11 N1 C10 C9 -59.2(7) . . . . ? C1 N1 C10 C9 178.5(6) . . . . ? Cu1 N1 C10 C9 50.7(6) . . . . ? N4 C9 C10 N1 -8.2(7) . . . . ? C1 N1 C11 C12 -165.5(6) . . . . ? C10 N1 C11 C12 71.4(7) . . . . ? Cu1 N1 C11 C12 -34.7(7) . . . . ? C8 N4 C12 C11 177.7(6) . . . . ? C9 N4 C12 C11 -58.3(7) . . . . ? Cu1 N4 C12 C11 48.8(6) . . . . ? N1 C11 C12 N4 -9.8(8) . . . . ? C4 N2 C13 C14 101.5(9) . . . . ? C3 N2 C13 C14 -135.6(8) . . . . ? Cu1 N2 C13 C14 -11.5(10) . . . . ? Cu1 O1 C14 O2 -179.7(6) . . . . ? Cu1 O1 C14 C13 1.4(10) . . . . ? C15 O2 C14 O1 9.6(12) . . . . ? C15 O2 C14 C13 -171.4(7) . . . . ? N2 C13 C14 O1 6.3(13) . . . . ? N2 C13 C14 O2 -172.8(7) . . . . ? C14 O2 C15 C18 -71.7(9) . . . . ? C14 O2 C15 C17 53.2(10) . . . . ? C14 O2 C15 C16 171.1(7) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.566 _refine_diff_density_min -1.187 _refine_diff_density_rms 0.169 # Attachment 'sja18_05.cif' data_sja18_05 _database_code_depnum_ccdc_archive 'CCDC 624742' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H30 Cu N4 O8, 4(H2 O)' _chemical_formula_sum 'C18 H38 Cu N4 O12' _chemical_formula_weight 566.06 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 8.5304(15) _cell_length_b 15.337(3) _cell_length_c 9.010(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.472(18) _cell_angle_gamma 90.00 _cell_volume 1178.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 598 _exptl_absorpt_coefficient_mu 0.997 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe IPDSII image plate' _diffrn_measurement_method '185 frames at 1^o intervals, exposure time 1 minute' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17146 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 34.78 _reflns_number_total 5072 _reflns_number_gt 4104 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-AREA _computing_cell_refinement X-AREA _computing_data_reduction X-RED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _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^)+(0.0654P)^2^+0.2425P] 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 SHELXL _refine_ls_extinction_coef 0.030(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5072 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1115 _refine_ls_wR_factor_gt 0.1065 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.127 _refine_ls_shift/su_max 0.058 _refine_ls_shift/su_mean 0.004 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 0.5000 0.5000 0.0000 0.01200(7) Uani 1 2 d S . . N1 N 0.33585(13) 0.48259(7) 0.16332(13) 0.01446(18) Uani 1 1 d . . . N2 N 0.65484(13) 0.40144(7) 0.09106(13) 0.01552(19) Uani 1 1 d . . . O1 O 0.58201(11) 0.60122(7) 0.16712(11) 0.01681(17) Uani 1 1 d . . . O2 O 0.57078(13) 0.61970(7) 0.41325(11) 0.0208(2) Uani 1 1 d . . . O3 O 0.89391(15) 0.29808(8) 0.25216(14) 0.0293(3) Uani 1 1 d . . . O4 O 0.91696(16) 0.40719(9) 0.41694(15) 0.0313(3) Uani 1 1 d . . . H4 H 0.9835 0.3753 0.4544 0.047 Uiso 1 1 calc R . . C1 C 0.29852(15) 0.38854(9) 0.19122(15) 0.0175(2) Uani 1 1 d . . . H11 H 0.2511 0.3645 0.1020 0.021 Uiso 1 1 calc R . . H12 H 0.2209 0.3855 0.2691 0.021 Uiso 1 1 calc R . . C2 C 0.43669(16) 0.33116(9) 0.23558(15) 0.0180(2) Uani 1 1 d . . . H21 H 0.3970 0.2739 0.2611 0.022 Uiso 1 1 calc R . . H22 H 0.4848 0.3555 0.3242 0.022 Uiso 1 1 calc R . . C3 C 0.56295(16) 0.32025(8) 0.11867(15) 0.0171(2) Uani 1 1 d . . . H31 H 0.6343 0.2745 0.1501 0.021 Uiso 1 1 calc R . . H32 H 0.5140 0.3018 0.0263 0.021 Uiso 1 1 calc R . . C4 C 0.76765(15) 0.38759(9) -0.03316(15) 0.0180(2) Uani 1 1 d . . . H41 H 0.7209 0.3498 -0.1077 0.022 Uiso 1 1 calc R . . H42 H 0.8621 0.3598 0.0043 0.022 Uiso 1 1 calc R . . C5 C 0.80803(15) 0.47483(10) -0.10154(15) 0.0177(2) Uani 1 1 d . . . H51 H 0.8552 0.5123 -0.0268 0.021 Uiso 1 1 calc R . . H52 H 0.8836 0.4665 -0.1801 0.021 Uiso 1 1 calc R . . C6 C 0.38263(15) 0.52637(9) 0.30505(14) 0.0157(2) Uani 1 1 d . . . H61 H 0.4069 0.4818 0.3781 0.019 Uiso 1 1 calc R . . H62 H 0.2936 0.5592 0.3413 0.019 Uiso 1 1 calc R . . C7 C 0.52322(14) 0.58808(8) 0.29386(14) 0.0150(2) Uani 1 1 d . . . C8 C 0.73916(15) 0.43142(9) 0.22572(15) 0.0170(2) Uani 1 1 d . . . H81 H 0.6616 0.4459 0.2998 0.020 Uiso 1 1 calc R . . H82 H 0.7937 0.4849 0.2011 0.020 Uiso 1 1 calc R . . C9 C 0.85780(16) 0.36943(10) 0.29712(16) 0.0199(2) Uani 1 1 d . . . O1W O 1.12568(13) 0.16831(8) 0.36304(13) 0.0228(2) Uani 1 1 d . . . H11W H 1.217(3) 0.1522(17) 0.342(3) 0.034 Uiso 1 1 d . . . H12W H 1.092(3) 0.1920(18) 0.286(3) 0.034 Uiso 1 1 d . . . O2W O 1.13316(13) 0.31324(8) 0.54101(13) 0.0229(2) Uani 1 1 d . . . H21W H 1.141(3) 0.2671(19) 0.495(3) 0.034 Uiso 1 1 d . . . H22W H 1.225(3) 0.3314(18) 0.552(3) 0.034 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 Cu1 0.01185(10) 0.01301(10) 0.01113(10) 0.00032(7) 0.00034(6) 0.00001(6) N1 0.0147(4) 0.0145(4) 0.0141(4) -0.0005(3) -0.0006(3) -0.0010(3) N2 0.0161(4) 0.0161(4) 0.0143(4) -0.0008(3) -0.0006(3) 0.0008(3) O1 0.0183(4) 0.0175(4) 0.0147(4) -0.0001(3) -0.0003(3) -0.0024(3) O2 0.0260(5) 0.0217(5) 0.0146(4) -0.0026(3) -0.0021(4) -0.0047(4) O3 0.0334(6) 0.0253(5) 0.0290(6) -0.0038(4) -0.0106(5) 0.0121(5) O4 0.0316(6) 0.0346(6) 0.0274(6) -0.0083(5) -0.0153(5) 0.0125(5) C1 0.0184(5) 0.0166(5) 0.0174(5) 0.0007(4) 0.0017(4) -0.0047(4) C2 0.0228(5) 0.0159(5) 0.0153(5) 0.0020(4) 0.0012(4) -0.0019(4) C3 0.0210(5) 0.0130(5) 0.0172(5) 0.0006(4) -0.0012(4) 0.0000(4) C4 0.0178(5) 0.0198(6) 0.0165(5) 0.0006(4) 0.0004(4) 0.0041(4) C5 0.0136(4) 0.0216(5) 0.0180(5) 0.0009(4) 0.0000(4) 0.0007(4) C6 0.0174(5) 0.0174(5) 0.0122(5) -0.0010(4) 0.0019(4) -0.0012(4) C7 0.0162(4) 0.0137(5) 0.0151(5) -0.0007(4) -0.0012(4) 0.0006(4) C8 0.0173(5) 0.0174(5) 0.0163(5) -0.0007(4) -0.0029(4) 0.0023(4) C9 0.0187(5) 0.0231(6) 0.0179(5) 0.0009(5) -0.0027(4) 0.0033(4) O1W 0.0197(4) 0.0281(5) 0.0205(5) 0.0033(4) -0.0005(4) 0.0042(4) O2W 0.0213(4) 0.0265(5) 0.0210(5) -0.0002(4) -0.0047(4) 0.0008(4) _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 N1 2.0571(12) . ? Cu1 N1 2.0571(12) 3_665 ? Cu1 N2 2.1644(12) . ? Cu1 N2 2.1644(12) 3_665 ? Cu1 O1 2.2693(10) . ? Cu1 O1 2.2693(10) 3_665 ? N1 C5 1.4938(17) 3_665 ? N1 C6 1.4942(17) . ? N1 C1 1.4990(17) . ? N2 C8 1.4787(17) . ? N2 C3 1.4934(17) . ? N2 C4 1.4972(18) . ? O1 C7 1.2672(16) . ? O2 C7 1.2449(16) . ? O3 C9 1.2077(19) . ? O4 C9 1.3216(19) . ? C1 C2 1.522(2) . ? C2 C3 1.522(2) . ? C4 C5 1.514(2) . ? C5 N1 1.4938(17) 3_665 ? C6 C7 1.5317(18) . ? C8 C9 1.5269(19) . ? 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 N1 Cu1 N1 180.00(6) . 3_665 ? N1 Cu1 N2 93.16(5) . . ? N1 Cu1 N2 86.84(5) 3_665 . ? N1 Cu1 N2 86.84(5) . 3_665 ? N1 Cu1 N2 93.16(5) 3_665 3_665 ? N2 Cu1 N2 180.0 . 3_665 ? N1 Cu1 O1 79.75(4) . . ? N1 Cu1 O1 100.25(4) 3_665 . ? N2 Cu1 O1 92.43(4) . . ? N2 Cu1 O1 87.57(4) 3_665 . ? N1 Cu1 O1 100.25(4) . 3_665 ? N1 Cu1 O1 79.75(4) 3_665 3_665 ? N2 Cu1 O1 87.57(4) . 3_665 ? N2 Cu1 O1 92.43(4) 3_665 3_665 ? O1 Cu1 O1 180.0 . 3_665 ? C5 N1 C6 109.56(10) 3_665 . ? C5 N1 C1 107.95(10) 3_665 . ? C6 N1 C1 110.17(10) . . ? C5 N1 Cu1 103.81(8) 3_665 . ? C6 N1 Cu1 112.00(8) . . ? C1 N1 Cu1 113.06(8) . . ? C8 N2 C3 112.03(11) . . ? C8 N2 C4 110.26(10) . . ? C3 N2 C4 110.34(10) . . ? C8 N2 Cu1 112.65(8) . . ? C3 N2 Cu1 109.03(8) . . ? C4 N2 Cu1 102.11(8) . . ? C7 O1 Cu1 111.54(8) . . ? N1 C1 C2 115.81(11) . . ? C1 C2 C3 115.65(11) . . ? N2 C3 C2 113.51(11) . . ? N2 C4 C5 109.18(11) . . ? N1 C5 C4 110.43(10) 3_665 . ? N1 C6 C7 115.16(10) . . ? O2 C7 O1 126.03(12) . . ? O2 C7 C6 115.69(12) . . ? O1 C7 C6 118.26(11) . . ? N2 C8 C9 117.93(11) . . ? O3 C9 O4 125.05(13) . . ? O3 C9 C8 126.36(13) . . ? O4 C9 C8 108.58(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 N1 C5 -163.64(8) . . . 3_665 ? N2 Cu1 N1 C5 16.36(8) 3_665 . . 3_665 ? O1 Cu1 N1 C5 104.46(8) . . . 3_665 ? O1 Cu1 N1 C5 -75.54(8) 3_665 . . 3_665 ? N2 Cu1 N1 C6 78.25(9) . . . . ? N2 Cu1 N1 C6 -101.75(9) 3_665 . . . ? O1 Cu1 N1 C6 -13.66(8) . . . . ? O1 Cu1 N1 C6 166.34(8) 3_665 . . . ? N2 Cu1 N1 C1 -46.93(9) . . . . ? N2 Cu1 N1 C1 133.07(9) 3_665 . . . ? O1 Cu1 N1 C1 -138.83(9) . . . . ? O1 Cu1 N1 C1 41.17(9) 3_665 . . . ? N1 Cu1 N2 C8 -75.00(9) . . . . ? N1 Cu1 N2 C8 105.00(9) 3_665 . . . ? O1 Cu1 N2 C8 4.86(9) . . . . ? O1 Cu1 N2 C8 -175.14(9) 3_665 . . . ? N1 Cu1 N2 C3 50.01(9) . . . . ? N1 Cu1 N2 C3 -129.99(9) 3_665 . . . ? O1 Cu1 N2 C3 129.87(8) . . . . ? O1 Cu1 N2 C3 -50.13(8) 3_665 . . . ? N1 Cu1 N2 C4 166.76(8) . . . . ? N1 Cu1 N2 C4 -13.24(8) 3_665 . . . ? O1 Cu1 N2 C4 -113.38(8) . . . . ? O1 Cu1 N2 C4 66.62(8) 3_665 . . . ? N1 Cu1 O1 C7 16.68(9) . . . . ? N1 Cu1 O1 C7 -163.32(9) 3_665 . . . ? N2 Cu1 O1 C7 -76.09(9) . . . . ? N2 Cu1 O1 C7 103.91(9) 3_665 . . . ? C5 N1 C1 C2 172.32(11) 3_665 . . . ? C6 N1 C1 C2 -68.08(14) . . . . ? Cu1 N1 C1 C2 58.08(13) . . . . ? N1 C1 C2 C3 -64.35(16) . . . . ? C8 N2 C3 C2 61.20(14) . . . . ? C4 N2 C3 C2 -175.55(11) . . . . ? Cu1 N2 C3 C2 -64.18(12) . . . . ? C1 C2 C3 N2 69.30(15) . . . . ? C8 N2 C4 C5 -79.24(13) . . . . ? C3 N2 C4 C5 156.48(11) . . . . ? Cu1 N2 C4 C5 40.69(11) . . . . ? N2 C4 C5 N1 -60.98(14) . . . 3_665 ? C5 N1 C6 C7 -103.87(12) 3_665 . . . ? C1 N1 C6 C7 137.52(11) . . . . ? Cu1 N1 C6 C7 10.77(13) . . . . ? Cu1 O1 C7 O2 163.28(11) . . . . ? Cu1 O1 C7 C6 -15.35(14) . . . . ? N1 C6 C7 O2 -174.67(11) . . . . ? N1 C6 C7 O1 4.09(17) . . . . ? C3 N2 C8 C9 59.31(15) . . . . ? C4 N2 C8 C9 -63.99(15) . . . . ? Cu1 N2 C8 C9 -177.34(9) . . . . ? N2 C8 C9 O3 2.2(2) . . . . ? N2 C8 C9 O4 -178.48(13) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 34.78 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.791 _refine_diff_density_min -0.791 _refine_diff_density_rms 0.101 # Attachment 'sja34_01.cif' data_sja34_01 _database_code_depnum_ccdc_archive 'CCDC 624743' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H30 Cu N4 O8, 2(H2 O)' _chemical_formula_sum 'C18 H34 Cu N4 O10' _chemical_formula_weight 530.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 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' 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.946(2) _cell_length_b 16.644(3) _cell_length_c 8.775(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.49(2) _cell_angle_gamma 90.00 _cell_volume 1155.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description lathe _exptl_crystal_colour violet _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 __exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 558 _exptl_absorpt_coefficient_mu 1.006 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe IPDSII image plate' _diffrn_measurement_method '185 frames at 1^o intervals, exposure time 1 minute' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16962 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 34.63 _reflns_number_total 4900 _reflns_number_gt 3379 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-AREA _computing_cell_refinement X-AREA _computing_data_reduction X-RED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _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^)+(0.0935P)^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 SHELXL _refine_ls_extinction_coef 0.033(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4900 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1428 _refine_ls_wR_factor_gt 0.1319 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.037 _refine_ls_shift/su_mean 0.003 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 0.0000 0.5000 0.02054(10) Uani 1 2 d S . . N1 N 0.12267(17) 0.06816(10) 0.35859(17) 0.0230(3) Uani 1 1 d . . . N2 N -0.10688(19) 0.12197(10) 0.59394(18) 0.0247(3) Uani 1 1 d . . . C1 C 0.1158(2) 0.15115(13) 0.4228(2) 0.0286(4) Uani 1 1 d . . . H1A H 0.1487 0.1893 0.3475 0.034 Uiso 1 1 calc R . . H1B H 0.1965 0.1553 0.5126 0.034 Uiso 1 1 calc R . . C2 C -0.0594(3) 0.17323(13) 0.4667(2) 0.0284(3) Uani 1 1 d . . . H2A H -0.0603 0.2292 0.4975 0.034 Uiso 1 1 calc R . . H2B H -0.1417 0.1665 0.3786 0.034 Uiso 1 1 calc R . . C3 C 0.3050(2) 0.04453(13) 0.3577(2) 0.0278(4) Uani 1 1 d . . . H3A H 0.3597 0.0514 0.4605 0.033 Uiso 1 1 calc R . . H3B H 0.3581 0.0817 0.2918 0.033 Uiso 1 1 calc R . . C4 C 0.3402(2) -0.04082(14) 0.3054(2) 0.0291(4) Uani 1 1 d . . . H4A H 0.4601 -0.0450 0.2942 0.035 Uiso 1 1 calc R . . H4B H 0.2808 -0.0483 0.2046 0.035 Uiso 1 1 calc R . . C5 C 0.2924(2) -0.11028(13) 0.4067(2) 0.0282(4) Uani 1 1 d . . . H5A H 0.3423 -0.1594 0.3721 0.034 Uiso 1 1 calc R . . H5B H 0.3400 -0.1004 0.5110 0.034 Uiso 1 1 calc R . . C6 C 0.0301(2) 0.06476(12) 0.20246(19) 0.0236(3) Uani 1 1 d . . . H6A H 0.0954 0.0333 0.1360 0.028 Uiso 1 1 calc R . . H6B H 0.0194 0.1187 0.1609 0.028 Uiso 1 1 calc R . . C7 C -0.1458(2) 0.02782(12) 0.2032(2) 0.0224(3) Uani 1 1 d . . . C8 C -0.0268(2) 0.14748(12) 0.7437(2) 0.0254(3) Uani 1 1 d . . . H8A H 0.0948 0.1454 0.7404 0.031 Uiso 1 1 calc R . . H8B H -0.0557 0.1087 0.8195 0.031 Uiso 1 1 calc R . . C9 C -0.0730(2) 0.23120(12) 0.7983(2) 0.0275(3) Uani 1 1 d . . . O1 O -0.18861(16) 0.00029(8) 0.32843(15) 0.0246(2) Uani 1 1 d . . . O2 O -0.23581(17) 0.02589(10) 0.07767(16) 0.0280(3) Uani 1 1 d . . . O3 O -0.0061(2) 0.24418(10) 0.94091(19) 0.0370(3) Uani 1 1 d . . . H3 H -0.0329 0.2891 0.9684 0.055 Uiso 1 1 calc R . . O4 O -0.1565(2) 0.28005(10) 0.72253(18) 0.0367(4) Uani 1 1 d . . . O5 O -0.04487(19) 0.39374(9) 1.02741(18) 0.0298(3) Uani 1 1 d . . . H51 H -0.108(4) 0.4287(19) 0.976(4) 0.045 Uiso 1 1 d . . . H52 H 0.050(4) 0.422(2) 1.044(4) 0.045 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 Cu1 0.01591(13) 0.03161(17) 0.01386(13) 0.00057(11) 0.00024(8) -0.00291(10) N1 0.0192(5) 0.0347(8) 0.0151(6) -0.0006(5) 0.0008(4) -0.0028(5) N2 0.0220(6) 0.0337(8) 0.0182(6) -0.0022(6) 0.0005(5) 0.0009(5) C1 0.0286(8) 0.0356(10) 0.0217(8) -0.0024(7) 0.0023(6) -0.0089(7) C2 0.0321(8) 0.0321(9) 0.0210(7) -0.0013(7) 0.0021(6) 0.0003(7) C3 0.0169(6) 0.0475(11) 0.0191(7) 0.0011(7) 0.0023(5) -0.0058(7) C4 0.0180(6) 0.0500(12) 0.0194(7) -0.0005(7) 0.0018(5) 0.0021(7) C5 0.0196(6) 0.0443(11) 0.0200(7) -0.0019(7) -0.0010(5) 0.0055(7) C6 0.0211(6) 0.0340(9) 0.0153(6) -0.0003(6) -0.0004(5) -0.0025(6) C7 0.0192(6) 0.0290(8) 0.0187(7) -0.0024(6) 0.0001(5) 0.0004(6) C8 0.0238(7) 0.0316(9) 0.0202(7) -0.0031(6) -0.0021(6) 0.0029(6) C9 0.0282(8) 0.0334(9) 0.0206(8) -0.0018(7) 0.0008(6) 0.0039(7) O1 0.0207(5) 0.0352(7) 0.0178(5) 0.0000(5) 0.0014(4) -0.0021(5) O2 0.0233(6) 0.0416(7) 0.0182(6) -0.0001(5) -0.0023(4) -0.0001(5) O3 0.0505(9) 0.0325(8) 0.0259(7) -0.0072(6) -0.0071(6) 0.0088(6) O4 0.0433(8) 0.0402(8) 0.0253(7) -0.0006(6) -0.0027(6) 0.0143(7) O5 0.0294(6) 0.0298(7) 0.0300(7) -0.0035(6) 0.0019(5) -0.0007(5) _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 N1 2.0020(15) . ? Cu1 N1 2.0020(15) 3_556 ? Cu1 O1 2.0202(15) . ? Cu1 O1 2.0202(15) 3_556 ? Cu1 N2 2.3782(17) . ? Cu1 N2 2.3782(17) 3_556 ? N1 C6 1.493(2) . ? N1 C1 1.495(3) . ? N1 C3 1.502(2) . ? N2 C8 1.467(2) . ? N2 C2 1.482(3) . ? N2 C5 1.486(2) 3_556 ? C1 C2 1.524(3) . ? C3 C4 1.527(3) . ? C4 C5 1.528(3) . ? C5 N2 1.486(2) 3_556 ? C6 C7 1.527(2) . ? C7 O2 1.255(2) . ? C7 O1 1.267(2) . ? C8 C9 1.529(3) . ? C9 O4 1.208(2) . ? C9 O3 1.330(2) . ? 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 N1 Cu1 N1 180.00(8) . 3_556 ? N1 Cu1 O1 84.68(6) . . ? N1 Cu1 O1 95.32(6) 3_556 . ? N1 Cu1 O1 95.32(6) . 3_556 ? N1 Cu1 O1 84.68(6) 3_556 3_556 ? O1 Cu1 O1 180.0 . 3_556 ? N1 Cu1 N2 86.69(6) . . ? N1 Cu1 N2 93.31(6) 3_556 . ? O1 Cu1 N2 89.55(5) . . ? O1 Cu1 N2 90.45(5) 3_556 . ? N1 Cu1 N2 93.31(6) . 3_556 ? N1 Cu1 N2 86.69(6) 3_556 3_556 ? O1 Cu1 N2 90.45(5) . 3_556 ? O1 Cu1 N2 89.55(5) 3_556 3_556 ? N2 Cu1 N2 180.0 . 3_556 ? C6 N1 C1 110.37(15) . . ? C6 N1 C3 112.11(14) . . ? C1 N1 C3 108.30(14) . . ? C6 N1 Cu1 108.72(11) . . ? C1 N1 Cu1 104.63(11) . . ? C3 N1 Cu1 112.45(12) . . ? C8 N2 C2 112.84(16) . . ? C8 N2 C5 112.74(14) . 3_556 ? C2 N2 C5 113.34(15) . 3_556 ? C8 N2 Cu1 114.77(11) . . ? C2 N2 Cu1 96.03(11) . . ? C5 N2 Cu1 105.89(12) 3_556 . ? N1 C1 C2 112.67(15) . . ? N2 C2 C1 110.86(16) . . ? N1 C3 C4 116.71(15) . . ? C3 C4 C5 117.79(16) . . ? N2 C5 C4 113.48(15) 3_556 . ? N1 C6 C7 112.48(14) . . ? O2 C7 O1 125.02(16) . . ? O2 C7 C6 116.87(16) . . ? O1 C7 C6 118.10(15) . . ? N2 C8 C9 116.61(16) . . ? O4 C9 O3 123.89(19) . . ? O4 C9 C8 125.20(18) . . ? O3 C9 C8 110.90(16) . . ? C7 O1 Cu1 113.93(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 N1 C6 106(89) 3_556 . . . ? O1 Cu1 N1 C6 -12.85(12) . . . . ? O1 Cu1 N1 C6 167.15(12) 3_556 . . . ? N2 Cu1 N1 C6 -102.71(12) . . . . ? N2 Cu1 N1 C6 77.29(12) 3_556 . . . ? N1 Cu1 N1 C1 -136(89) 3_556 . . . ? O1 Cu1 N1 C1 105.08(11) . . . . ? O1 Cu1 N1 C1 -74.92(11) 3_556 . . . ? N2 Cu1 N1 C1 15.22(11) . . . . ? N2 Cu1 N1 C1 -164.78(11) 3_556 . . . ? N1 Cu1 N1 C3 -18(89) 3_556 . . . ? O1 Cu1 N1 C3 -137.60(13) . . . . ? O1 Cu1 N1 C3 42.40(13) 3_556 . . . ? N2 Cu1 N1 C3 132.54(13) . . . . ? N2 Cu1 N1 C3 -47.46(13) 3_556 . . . ? N1 Cu1 N2 C8 -104.05(13) . . . . ? N1 Cu1 N2 C8 75.95(13) 3_556 . . . ? O1 Cu1 N2 C8 171.25(13) . . . . ? O1 Cu1 N2 C8 -8.75(13) 3_556 . . . ? N2 Cu1 N2 C8 12(100) 3_556 . . . ? N1 Cu1 N2 C2 14.55(11) . . . . ? N1 Cu1 N2 C2 -165.45(11) 3_556 . . . ? O1 Cu1 N2 C2 -70.14(11) . . . . ? O1 Cu1 N2 C2 109.86(11) 3_556 . . . ? N2 Cu1 N2 C2 131(100) 3_556 . . . ? N1 Cu1 N2 C5 130.93(12) . . . 3_556 ? N1 Cu1 N2 C5 -49.07(12) 3_556 . . 3_556 ? O1 Cu1 N2 C5 46.23(12) . . . 3_556 ? O1 Cu1 N2 C5 -133.77(12) 3_556 . . 3_556 ? N2 Cu1 N2 C5 -113(100) 3_556 . . 3_556 ? C6 N1 C1 C2 71.49(19) . . . . ? C3 N1 C1 C2 -165.44(16) . . . . ? Cu1 N1 C1 C2 -45.30(18) . . . . ? C8 N2 C2 C1 78.59(19) . . . . ? C5 N2 C2 C1 -151.72(16) 3_556 . . . ? Cu1 N2 C2 C1 -41.51(15) . . . . ? N1 C1 C2 N2 65.0(2) . . . . ? C6 N1 C3 C4 -61.7(2) . . . . ? C1 N1 C3 C4 176.25(16) . . . . ? Cu1 N1 C3 C4 61.13(18) . . . . ? N1 C3 C4 C5 -67.1(2) . . . . ? C3 C4 C5 N2 70.4(2) . . . 3_556 ? C1 N1 C6 C7 -101.37(17) . . . . ? C3 N1 C6 C7 137.80(17) . . . . ? Cu1 N1 C6 C7 12.85(18) . . . . ? N1 C6 C7 O2 176.85(17) . . . . ? N1 C6 C7 O1 -4.4(2) . . . . ? C2 N2 C8 C9 62.8(2) . . . . ? C5 N2 C8 C9 -67.2(2) 3_556 . . . ? Cu1 N2 C8 C9 171.49(12) . . . . ? N2 C8 C9 O4 -7.3(3) . . . . ? N2 C8 C9 O3 173.80(16) . . . . ? O2 C7 O1 Cu1 171.97(16) . . . . ? C6 C7 O1 Cu1 -6.7(2) . . . . ? N1 Cu1 O1 C7 11.43(14) . . . . ? N1 Cu1 O1 C7 -168.57(14) 3_556 . . . ? O1 Cu1 O1 C7 -46(100) 3_556 . . . ? N2 Cu1 O1 C7 98.15(13) . . . . ? N2 Cu1 O1 C7 -81.85(13) 3_556 . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 34.63 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.957 _refine_diff_density_min -1.212 _refine_diff_density_rms 0.114 # Attachment 'sja19_04.cif' data_sja19_04 _database_code_depnum_ccdc_archive 'CCDC 624744' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H28 Cu N4 O2, 2(Cl O4), 2(H2 O)' _chemical_formula_sum 'C14 H32 Cl2 Cu N4 O12' _chemical_formula_weight 582.88 _chemical_absolute_configuration unk 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' 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.0640(15) _cell_length_b 9.4730(11) _cell_length_c 17.359(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2312.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description lathe _exptl_crystal_colour blue _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 1.243 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27974 _diffrn_reflns_av_R_equivalents 0.1298 _diffrn_reflns_av_sigmaI/netI 0.0936 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 32.54 _reflns_number_total 8246 _reflns_number_gt 4976 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-AREA _computing_cell_refinement X-AREA _computing_data_reduction X-RED _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP II (Johnson, 1976)' _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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.48(4) _refine_ls_number_reflns 8246 _refine_ls_number_parameters 319 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1522 _refine_ls_R_factor_gt 0.1132 _refine_ls_wR_factor_ref 0.3102 _refine_ls_wR_factor_gt 0.2791 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.008 _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 0.18976(4) 0.50449(9) 0.04001(4) 0.0348(2) Uani 1 1 d . . . Cl1 Cl 0.05985(17) 0.5516(3) 0.39998(14) 0.0637(6) Uani 1 1 d . . . Cl2 Cl 0.40329(18) -0.0211(3) 0.27382(13) 0.0644(6) Uani 1 1 d . . . N1 N 0.2046(5) 0.7185(8) 0.0520(5) 0.0556(16) Uani 1 1 d . . . N2 N 0.1100(4) 0.4924(10) -0.0571(3) 0.0521(14) Uani 1 1 d . . . N3 N 0.2413(6) 0.3127(9) 0.0124(5) 0.0576(17) Uani 1 1 d . . . H14 H 0.3013 0.3279 -0.0086 0.069 Uiso 1 1 calc R . . N4 N 0.2592(5) 0.5303(12) 0.1398(4) 0.067(3) Uani 1 1 d . . . C1 C 0.1681(9) 0.8151(12) -0.0062(10) 0.084(4) Uani 1 1 d . . . H1A H 0.2193 0.8376 -0.0434 0.101 Uiso 1 1 calc R . . H1B H 0.1482 0.9042 0.0188 0.101 Uiso 1 1 calc R . . C2 C 0.0829(7) 0.7514(12) -0.0499(7) 0.067(2) Uani 1 1 d . . . H2A H 0.0342 0.7219 -0.0120 0.081 Uiso 1 1 calc R . . H2B H 0.0543 0.8256 -0.0827 0.081 Uiso 1 1 calc R . . C3 C 0.1086(7) 0.6240(12) -0.1007(5) 0.060(2) Uani 1 1 d . . . H3A H 0.0618 0.6160 -0.1430 0.072 Uiso 1 1 calc R . . H3B H 0.1720 0.6396 -0.1240 0.072 Uiso 1 1 calc R . . C4 C 0.1529(7) 0.3746(15) -0.1011(6) 0.074(3) Uani 1 1 d . . . H4A H 0.1062 0.3389 -0.1391 0.089 Uiso 1 1 calc R . . H4B H 0.2089 0.4098 -0.1298 0.089 Uiso 1 1 calc R . . C5 C 0.1825(7) 0.2576(10) -0.0500(6) 0.0601(19) Uani 1 1 d . . . H5A H 0.1256 0.2105 -0.0284 0.072 Uiso 1 1 calc R . . H5B H 0.2189 0.1869 -0.0800 0.072 Uiso 1 1 calc R . . C6 C 0.2555(8) 0.2178(12) 0.0792(6) 0.065(2) Uani 1 1 d . . . H6A H 0.2800 0.1254 0.0615 0.078 Uiso 1 1 calc R . . H6B H 0.1941 0.2019 0.1058 0.078 Uiso 1 1 calc R . . C7 C 0.3267(9) 0.2860(13) 0.1349(7) 0.073(3) Uani 1 1 d . . . H7A H 0.3528 0.2114 0.1689 0.087 Uiso 1 1 calc R . . H7B H 0.3802 0.3248 0.1045 0.087 Uiso 1 1 calc R . . C8 C 0.2866(8) 0.4032(16) 0.1853(6) 0.078(3) Uani 1 1 d . . . H8A H 0.2300 0.3674 0.2130 0.094 Uiso 1 1 calc R . . H8B H 0.3347 0.4304 0.2241 0.094 Uiso 1 1 calc R . . C9 C 0.1958(8) 0.6238(14) 0.1844(5) 0.070(3) Uani 1 1 d . . . H9A H 0.2303 0.6632 0.2292 0.084 Uiso 1 1 calc R . . H9B H 0.1404 0.5698 0.2036 0.084 Uiso 1 1 calc R . . C10 C 0.1628(8) 0.7419(12) 0.1321(7) 0.068(3) Uani 1 1 d . . . H10A H 0.1842 0.8340 0.1528 0.081 Uiso 1 1 calc R . . H10B H 0.0925 0.7426 0.1293 0.081 Uiso 1 1 calc R . . C11 C 0.3097(7) 0.7340(10) 0.0627(6) 0.062(2) Uani 1 1 d . . . H11A H 0.3241 0.8265 0.0865 0.074 Uiso 1 1 calc R . . H11B H 0.3421 0.7294 0.0121 0.074 Uiso 1 1 calc R . . C12 C 0.3451(7) 0.6146(12) 0.1147(6) 0.061(2) Uani 1 1 d . . . H12A H 0.3900 0.5534 0.0862 0.074 Uiso 1 1 calc R . . H12B H 0.3783 0.6539 0.1601 0.074 Uiso 1 1 calc R . . C13 C 0.0100(6) 0.4468(12) -0.0367(5) 0.0585(19) Uani 1 1 d . . . H13A H -0.0358 0.5030 -0.0672 0.070 Uiso 1 1 calc R . . H13B H 0.0016 0.3464 -0.0510 0.070 Uiso 1 1 calc R . . C14 C -0.0115(5) 0.4636(10) 0.0442(5) 0.0553(19) Uani 1 1 d . . . O1 O 0.0477(4) 0.4745(9) 0.0939(3) 0.0586(17) Uani 1 1 d . . . O2 O -0.1040(4) 0.4722(10) 0.0594(4) 0.0651(19) Uani 1 1 d D . . H15 H -0.138(9) 0.559(8) 0.053(7) 0.078 Uiso 1 1 d D . . O3 O 0.1257(14) 0.4465(15) 0.4016(11) 0.162(7) Uani 1 1 d . . . O4 O -0.0155(10) 0.4973(18) 0.3550(9) 0.158(7) Uani 1 1 d . . . O5 O 0.1025(8) 0.6726(14) 0.3625(7) 0.106(3) Uani 1 1 d . . . O6 O 0.0323(12) 0.5943(18) 0.4765(7) 0.131(5) Uani 1 1 d . . . O7 O 0.3350(7) 0.0789(16) 0.3035(7) 0.121(5) Uani 1 1 d . . . O8 O 0.4453(16) -0.077(2) 0.3425(9) 0.173(8) Uani 1 1 d . . . O9 O 0.4680(11) 0.086(3) 0.2440(9) 0.188(10) Uani 1 1 d . . . O10 O 0.356(2) -0.091(3) 0.225(2) 0.35(2) Uani 1 1 d . . . O11 O -0.1393(5) 0.5011(17) 0.2004(5) 0.096(3) Uani 1 1 d D . . O12 O -0.0583(11) 0.7571(14) 0.2477(6) 0.108(4) Uani 1 1 d D . . H111 H -0.148(5) 0.457(7) 0.150(2) 0.023(16) Uiso 1 1 d D . . H112 H -0.094(6) 0.424(8) 0.201(6) 0.05(3) Uiso 1 1 d D . . H113 H -0.013(5) 0.748(9) 0.289(3) 0.033(19) Uiso 1 1 d D . . H114 H -0.039(7) 0.855(4) 0.248(5) 0.04(2) Uiso 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 0.0304(3) 0.0411(3) 0.0331(3) 0.0010(4) -0.0027(2) -0.0012(4) Cl1 0.0506(9) 0.0815(15) 0.0590(10) 0.0044(10) -0.0009(8) -0.0101(10) Cl2 0.0667(11) 0.0690(15) 0.0576(10) 0.0011(10) 0.0116(8) 0.0020(11) N1 0.044(3) 0.061(4) 0.061(4) -0.001(3) 0.000(3) 0.000(3) N2 0.042(2) 0.071(4) 0.044(3) -0.002(4) -0.0070(19) -0.007(4) N3 0.045(3) 0.067(5) 0.060(4) 0.004(3) 0.009(3) 0.006(3) N4 0.049(3) 0.116(9) 0.037(3) 0.000(4) -0.008(2) -0.003(4) C1 0.057(6) 0.058(5) 0.137(12) 0.028(7) -0.009(6) -0.004(5) C2 0.049(4) 0.074(6) 0.079(6) 0.023(5) -0.014(4) 0.004(4) C3 0.051(4) 0.087(6) 0.043(4) 0.013(4) -0.013(3) -0.006(5) C4 0.045(4) 0.115(9) 0.063(5) -0.034(6) -0.006(4) -0.018(5) C5 0.052(4) 0.064(5) 0.064(5) -0.013(4) 0.000(4) -0.006(4) C6 0.058(5) 0.066(6) 0.070(5) 0.018(4) 0.006(4) 0.018(4) C7 0.067(6) 0.082(7) 0.069(6) 0.024(5) -0.005(5) 0.015(5) C8 0.056(5) 0.122(10) 0.057(5) 0.031(6) -0.011(4) 0.015(6) C9 0.055(5) 0.106(8) 0.050(4) -0.022(5) -0.003(4) -0.013(5) C10 0.054(4) 0.068(6) 0.081(6) -0.022(5) 0.000(4) 0.012(4) C11 0.045(4) 0.058(4) 0.081(6) 0.007(4) -0.005(4) -0.015(4) C12 0.047(4) 0.079(6) 0.058(5) -0.010(4) -0.018(4) -0.002(4) C13 0.039(3) 0.081(5) 0.055(4) 0.005(4) -0.002(3) -0.007(3) C14 0.039(3) 0.075(5) 0.052(3) 0.022(4) 0.004(3) -0.006(3) O1 0.037(2) 0.094(5) 0.045(2) 0.004(3) 0.0062(18) -0.006(3) O2 0.036(2) 0.098(6) 0.061(3) 0.010(3) 0.006(2) -0.003(3) O3 0.207(19) 0.089(8) 0.190(15) 0.038(10) 0.035(15) 0.029(10) O4 0.134(10) 0.188(14) 0.152(10) 0.063(11) -0.082(9) -0.108(11) O5 0.098(8) 0.102(8) 0.117(8) -0.006(7) 0.010(7) -0.016(6) O6 0.129(11) 0.176(13) 0.089(7) 0.007(8) 0.017(8) 0.013(10) O7 0.063(5) 0.188(12) 0.111(8) -0.078(8) 0.009(5) 0.021(6) O8 0.210(18) 0.169(15) 0.140(13) 0.059(11) -0.071(13) -0.083(14) O9 0.107(10) 0.33(3) 0.126(10) 0.084(14) 0.022(8) -0.076(13) O10 0.30(4) 0.31(4) 0.44(4) -0.26(3) -0.23(3) 0.04(3) O11 0.054(3) 0.164(10) 0.068(4) -0.004(7) 0.011(3) -0.012(7) O12 0.138(11) 0.100(8) 0.085(6) 0.003(6) -0.006(7) 0.011(7) _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 N4 2.003(7) . ? Cu1 N3 2.015(8) . ? Cu1 N2 2.028(5) . ? Cu1 N1 2.049(8) . ? Cu1 O1 2.225(5) . ? Cl1 O3 1.360(16) . ? Cl1 O4 1.413(9) . ? Cl1 O6 1.442(13) . ? Cl1 O5 1.448(13) . ? Cl2 O10 1.261(15) . ? Cl2 O8 1.431(15) . ? Cl2 O7 1.444(10) . ? Cl2 O9 1.457(15) . ? N1 C1 1.458(15) . ? N1 C11 1.496(11) . ? N1 C10 1.526(13) . ? N2 C3 1.459(13) . ? N2 C4 1.480(14) . ? N2 C13 1.514(10) . ? N3 C5 1.460(12) . ? N3 C6 1.481(13) . ? N4 C9 1.476(14) . ? N4 C8 1.490(15) . ? N4 C12 1.512(13) . ? C1 C2 1.540(16) . ? C2 C3 1.539(17) . ? C4 C5 1.479(18) . ? C6 C7 1.535(17) . ? C7 C8 1.522(19) . ? C9 C10 1.513(18) . ? C11 C12 1.531(14) . ? C13 C14 1.445(12) . ? C14 O1 1.203(10) . ? C14 O2 1.329(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 N4 Cu1 N3 98.1(4) . . ? N4 Cu1 N2 174.3(4) . . ? N3 Cu1 N2 87.1(4) . . ? N4 Cu1 N1 75.0(4) . . ? N3 Cu1 N1 151.7(3) . . ? N2 Cu1 N1 101.4(3) . . ? N4 Cu1 O1 95.2(3) . . ? N3 Cu1 O1 108.0(3) . . ? N2 Cu1 O1 81.1(2) . . ? N1 Cu1 O1 100.1(3) . . ? O3 Cl1 O4 104.8(12) . . ? O3 Cl1 O6 111.7(11) . . ? O4 Cl1 O6 114.2(10) . . ? O3 Cl1 O5 107.8(9) . . ? O4 Cl1 O5 110.5(8) . . ? O6 Cl1 O5 107.7(9) . . ? O10 Cl2 O8 126(2) . . ? O10 Cl2 O7 103.6(15) . . ? O8 Cl2 O7 102.6(12) . . ? O10 Cl2 O9 117(2) . . ? O8 Cl2 O9 107.1(10) . . ? O7 Cl2 O9 94.9(12) . . ? C1 N1 C11 111.9(8) . . ? C1 N1 C10 113.9(9) . . ? C11 N1 C10 104.7(8) . . ? C1 N1 Cu1 120.9(8) . . ? C11 N1 Cu1 102.1(5) . . ? C10 N1 Cu1 101.4(6) . . ? C3 N2 C4 112.5(8) . . ? C3 N2 C13 110.7(7) . . ? C4 N2 C13 106.5(8) . . ? C3 N2 Cu1 112.9(6) . . ? C4 N2 Cu1 104.2(6) . . ? C13 N2 Cu1 109.6(5) . . ? C5 N3 C6 116.2(8) . . ? C5 N3 Cu1 107.1(6) . . ? C6 N3 Cu1 114.1(6) . . ? C9 N4 C8 111.3(9) . . ? C9 N4 C12 108.5(10) . . ? C8 N4 C12 111.9(8) . . ? C9 N4 Cu1 103.4(6) . . ? C8 N4 Cu1 119.0(8) . . ? C12 N4 Cu1 101.8(5) . . ? N1 C1 C2 111.7(9) . . ? C3 C2 C1 114.0(9) . . ? N2 C3 C2 112.1(8) . . ? C5 C4 N2 111.7(8) . . ? N3 C5 C4 109.6(8) . . ? N3 C6 C7 109.0(9) . . ? C8 C7 C6 115.2(9) . . ? N4 C8 C7 112.4(9) . . ? N4 C9 C10 108.3(8) . . ? C9 C10 N1 108.8(8) . . ? N1 C11 C12 108.8(7) . . ? N4 C12 C11 107.5(7) . . ? C14 C13 N2 113.0(7) . . ? O1 C14 O2 122.0(8) . . ? O1 C14 C13 124.1(7) . . ? O2 C14 C13 113.8(7) . . ? C14 O1 Cu1 109.4(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N4 Cu1 N1 C1 179.7(9) . . . . ? N3 Cu1 N1 C1 100.7(10) . . . . ? N2 Cu1 N1 C1 -4.8(9) . . . . ? O1 Cu1 N1 C1 -87.6(8) . . . . ? N4 Cu1 N1 C11 54.7(6) . . . . ? N3 Cu1 N1 C11 -24.3(10) . . . . ? N2 Cu1 N1 C11 -129.7(6) . . . . ? O1 Cu1 N1 C11 147.4(6) . . . . ? N4 Cu1 N1 C10 -53.2(6) . . . . ? N3 Cu1 N1 C10 -132.3(7) . . . . ? N2 Cu1 N1 C10 122.3(5) . . . . ? O1 Cu1 N1 C10 39.5(6) . . . . ? N4 Cu1 N2 C3 66(4) . . . . ? N3 Cu1 N2 C3 -136.9(7) . . . . ? N1 Cu1 N2 C3 15.8(7) . . . . ? O1 Cu1 N2 C3 114.4(7) . . . . ? N4 Cu1 N2 C4 -172(4) . . . . ? N3 Cu1 N2 C4 -14.5(7) . . . . ? N1 Cu1 N2 C4 138.2(7) . . . . ? O1 Cu1 N2 C4 -123.2(7) . . . . ? N4 Cu1 N2 C13 -58(4) . . . . ? N3 Cu1 N2 C13 99.2(7) . . . . ? N1 Cu1 N2 C13 -108.1(7) . . . . ? O1 Cu1 N2 C13 -9.5(7) . . . . ? N4 Cu1 N3 C5 166.6(6) . . . . ? N2 Cu1 N3 C5 -11.3(6) . . . . ? N1 Cu1 N3 C5 -120.1(7) . . . . ? O1 Cu1 N3 C5 68.4(6) . . . . ? N4 Cu1 N3 C6 36.5(7) . . . . ? N2 Cu1 N3 C6 -141.3(7) . . . . ? N1 Cu1 N3 C6 109.8(9) . . . . ? O1 Cu1 N3 C6 -61.6(7) . . . . ? N3 Cu1 N4 C9 -152.1(7) . . . . ? N2 Cu1 N4 C9 5(4) . . . . ? N1 Cu1 N4 C9 56.0(7) . . . . ? O1 Cu1 N4 C9 -43.1(8) . . . . ? N3 Cu1 N4 C8 -28.1(8) . . . . ? N2 Cu1 N4 C8 129(4) . . . . ? N1 Cu1 N4 C8 180.0(8) . . . . ? O1 Cu1 N4 C8 80.9(8) . . . . ? N3 Cu1 N4 C12 95.4(7) . . . . ? N2 Cu1 N4 C12 -107(3) . . . . ? N1 Cu1 N4 C12 -56.5(7) . . . . ? O1 Cu1 N4 C12 -155.6(7) . . . . ? C11 N1 C1 C2 147.7(10) . . . . ? C10 N1 C1 C2 -93.7(13) . . . . ? Cu1 N1 C1 C2 27.4(15) . . . . ? N1 C1 C2 C3 -67.3(15) . . . . ? C4 N2 C3 C2 -168.6(7) . . . . ? C13 N2 C3 C2 72.4(9) . . . . ? Cu1 N2 C3 C2 -50.9(9) . . . . ? C1 C2 C3 N2 84.3(11) . . . . ? C3 N2 C4 C5 161.4(7) . . . . ? C13 N2 C4 C5 -77.1(8) . . . . ? Cu1 N2 C4 C5 38.7(9) . . . . ? C6 N3 C5 C4 164.3(8) . . . . ? Cu1 N3 C5 C4 35.4(9) . . . . ? N2 C4 C5 N3 -51.4(10) . . . . ? C5 N3 C6 C7 174.3(8) . . . . ? Cu1 N3 C6 C7 -60.3(9) . . . . ? N3 C6 C7 C8 77.7(11) . . . . ? C9 N4 C8 C7 163.2(9) . . . . ? C12 N4 C8 C7 -75.2(12) . . . . ? Cu1 N4 C8 C7 43.2(11) . . . . ? C6 C7 C8 N4 -67.1(13) . . . . ? C8 N4 C9 C10 -174.1(9) . . . . ? C12 N4 C9 C10 62.3(9) . . . . ? Cu1 N4 C9 C10 -45.2(10) . . . . ? N4 C9 C10 N1 1.7(11) . . . . ? C1 N1 C10 C9 172.4(9) . . . . ? C11 N1 C10 C9 -65.1(10) . . . . ? Cu1 N1 C10 C9 40.8(9) . . . . ? C1 N1 C11 C12 -171.1(10) . . . . ? C10 N1 C11 C12 65.0(10) . . . . ? Cu1 N1 C11 C12 -40.3(9) . . . . ? C9 N4 C12 C11 -61.9(9) . . . . ? C8 N4 C12 C11 174.9(9) . . . . ? Cu1 N4 C12 C11 46.8(9) . . . . ? N1 C11 C12 N4 -3.3(11) . . . . ? C3 N2 C13 C14 -108.2(9) . . . . ? C4 N2 C13 C14 129.2(9) . . . . ? Cu1 N2 C13 C14 17.0(11) . . . . ? N2 C13 C14 O1 -19.3(15) . . . . ? N2 C13 C14 O2 157.9(8) . . . . ? O2 C14 O1 Cu1 -166.7(8) . . . . ? C13 C14 O1 Cu1 10.4(13) . . . . ? N4 Cu1 O1 C14 176.3(8) . . . . ? N3 Cu1 O1 C14 -83.5(7) . . . . ? N2 Cu1 O1 C14 0.5(7) . . . . ? N1 Cu1 O1 C14 100.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 32.54 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.192 _refine_diff_density_min -0.665 _refine_diff_density_rms 0.177