Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_sm39 _database_code_depnum_ccdc_archive 'CCDC 248271' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 Cu N3 O2' _chemical_formula_weight 336.87 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 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 10.765(2) _cell_length_b 8.0480(10) _cell_length_c 16.946(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.380(10) _cell_angle_gamma 90.00 _cell_volume 1456.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 4.58 _cell_measurement_theta_max 12.51 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 1.508 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.4931 _exptl_absorpt_correction_T_max 0.7561 _exptl_absorpt_process_details 'North et al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 3460 _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 24.98 _reflns_number_total 2558 _reflns_number_gt 2411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0452P)^2^+0.9705P] 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 2558 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0317 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0826 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _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 0.83308(2) 0.16937(3) 0.369473(14) 0.01081(12) Uani 1 1 d . . . N1 N 0.80050(17) 0.1009(2) 0.25920(11) 0.0172(4) Uani 1 1 d . . . C111 C 0.78170(19) 0.0308(3) 0.19870(12) 0.0131(4) Uani 1 1 d . . . O111 O 0.76247(15) -0.03786(19) 0.13442(9) 0.0204(4) Uani 1 1 d . . . O1 O 0.99713(14) 0.24686(19) 0.35329(8) 0.0164(3) Uani 1 1 d . . . C2 C 1.0799(2) 0.3085(2) 0.40750(13) 0.0122(4) Uani 1 1 d . . . C3 C 1.0718(2) 0.3065(3) 0.48825(13) 0.0135(4) Uani 1 1 d . . . H3 H 1.1395 0.3545 0.5222 0.016 Uiso 1 1 calc R . . C4 C 0.9715(2) 0.2392(2) 0.52528(12) 0.0129(4) Uani 1 1 d . . . N5 N 0.86791(17) 0.1839(2) 0.48446(11) 0.0120(4) Uani 1 1 d . . . C6 C 0.7653(2) 0.1243(3) 0.52597(12) 0.0154(4) Uani 1 1 d . . . H6A H 0.7628 0.1872 0.5759 0.018 Uiso 1 1 calc R . . H6B H 0.7766 0.0050 0.5392 0.018 Uiso 1 1 calc R . . C7 C 0.6451(2) 0.1506(3) 0.47008(13) 0.0152(5) Uani 1 1 d . . . H7A H 0.5750 0.0943 0.4916 0.018 Uiso 1 1 calc R . . H7B H 0.6259 0.2708 0.4659 0.018 Uiso 1 1 calc R . . N8 N 0.65814(17) 0.0830(2) 0.39003(11) 0.0134(4) Uani 1 1 d . . . C9 C 0.5526(2) 0.1419(3) 0.33219(14) 0.0182(5) Uani 1 1 d . . . H9A H 0.5600 0.0951 0.2796 0.027 Uiso 1 1 calc R . . H9B H 0.5545 0.2635 0.3293 0.027 Uiso 1 1 calc R . . H9C H 0.4732 0.1061 0.3494 0.027 Uiso 1 1 calc R . . C10 C 0.6584(2) -0.1007(3) 0.38999(14) 0.0185(5) Uani 1 1 d . . . H10A H 0.5784 -0.1415 0.4042 0.028 Uiso 1 1 calc R . . H10B H 0.7270 -0.1412 0.4288 0.028 Uiso 1 1 calc R . . H10C H 0.6698 -0.1412 0.3369 0.028 Uiso 1 1 calc R . . C11 C 0.9893(2) 0.2336(3) 0.61511(12) 0.0171(5) Uani 1 1 d . . . H11A H 0.9262 0.3040 0.6354 0.026 Uiso 1 1 calc R . . H11B H 1.0732 0.2743 0.6353 0.026 Uiso 1 1 calc R . . H11C H 0.9800 0.1190 0.6329 0.026 Uiso 1 1 calc R . . C12 C 1.1910(2) 0.3856(2) 0.37677(12) 0.0124(4) Uani 1 1 d . . . C13 C 1.2986(2) 0.4379(3) 0.42639(13) 0.0151(4) Uani 1 1 d . . . H13 H 1.3043 0.4213 0.4822 0.018 Uiso 1 1 calc R . . C14 C 1.3969(2) 0.5137(3) 0.39438(13) 0.0172(5) Uani 1 1 d . . . H14 H 1.4691 0.5482 0.4286 0.021 Uiso 1 1 calc R . . C15 C 1.3908(2) 0.5397(3) 0.31278(13) 0.0160(4) Uani 1 1 d . . . H15 H 1.4579 0.5921 0.2912 0.019 Uiso 1 1 calc R . . C16 C 1.2847(2) 0.4876(3) 0.26335(13) 0.0168(5) Uani 1 1 d . . . H16 H 1.2791 0.5054 0.2076 0.020 Uiso 1 1 calc R . . C17 C 1.1872(2) 0.4100(3) 0.29477(12) 0.0142(4) Uani 1 1 d . . . H17 H 1.1164 0.3726 0.2600 0.017 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 0.00982(18) 0.01334(17) 0.00981(17) -0.00064(8) 0.00328(11) -0.00216(9) N1 0.0151(9) 0.0236(10) 0.0135(9) -0.0032(8) 0.0042(7) -0.0048(8) C111 0.0087(10) 0.0141(9) 0.0169(11) 0.0048(9) 0.0033(8) 0.0019(8) O111 0.0293(9) 0.0189(8) 0.0123(8) -0.0045(6) -0.0003(6) 0.0017(7) O1 0.0135(8) 0.0242(8) 0.0123(7) -0.0015(6) 0.0040(6) -0.0057(7) C2 0.0124(11) 0.0089(9) 0.0156(11) -0.0009(8) 0.0026(8) 0.0008(8) C3 0.0112(11) 0.0144(9) 0.0144(10) -0.0010(8) 0.0001(8) 0.0006(8) C4 0.0155(11) 0.0109(10) 0.0127(10) 0.0002(8) 0.0033(8) 0.0037(8) N5 0.0123(9) 0.0126(8) 0.0121(9) 0.0012(6) 0.0052(7) 0.0004(7) C6 0.0157(11) 0.0175(10) 0.0140(10) 0.0003(8) 0.0053(9) -0.0034(9) C7 0.0134(11) 0.0159(10) 0.0178(11) -0.0029(8) 0.0075(9) -0.0031(9) N8 0.0140(9) 0.0116(8) 0.0153(9) -0.0005(7) 0.0041(7) -0.0009(7) C9 0.0105(11) 0.0221(11) 0.0216(12) -0.0023(9) 0.0003(9) -0.0012(9) C10 0.0217(12) 0.0111(10) 0.0247(12) -0.0011(9) 0.0105(9) -0.0031(9) C11 0.0155(11) 0.0239(11) 0.0125(10) 0.0002(9) 0.0035(8) 0.0002(9) C12 0.0127(10) 0.0086(9) 0.0166(10) -0.0009(8) 0.0036(8) 0.0019(8) C13 0.0138(10) 0.0163(10) 0.0151(10) 0.0013(8) 0.0019(8) 0.0000(9) C14 0.0120(10) 0.0161(10) 0.0230(11) -0.0015(9) 0.0005(9) -0.0017(9) C15 0.0119(10) 0.0141(10) 0.0237(11) 0.0031(8) 0.0089(9) 0.0020(8) C16 0.0177(11) 0.0180(11) 0.0162(10) 0.0010(8) 0.0072(9) 0.0016(9) C17 0.0133(10) 0.0150(10) 0.0145(10) -0.0018(8) 0.0020(8) 0.0008(8) _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 O1 1.9254(15) . ? Cu1 N1 1.9365(18) . ? Cu1 N5 1.9399(18) . ? Cu1 N8 2.0783(18) . ? N1 C111 1.165(3) . ? C111 O111 1.215(3) . ? O1 C2 1.293(3) . ? C2 C3 1.382(3) . ? C2 C12 1.500(3) . ? C3 C4 1.424(3) . ? C3 H3 0.9500 . ? C4 N5 1.312(3) . ? C4 C11 1.510(3) . ? N5 C6 1.465(3) . ? C6 C7 1.516(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N8 1.485(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C10 1.479(3) . ? N8 C9 1.480(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.399(3) . ? C12 C13 1.406(3) . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C15 1.392(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 C17 1.385(3) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N1 90.59(7) . . ? O1 Cu1 N5 93.50(7) . . ? N1 Cu1 N5 166.94(7) . . ? O1 Cu1 N8 178.38(7) . . ? N1 Cu1 N8 90.63(7) . . ? N5 Cu1 N8 85.08(7) . . ? C111 N1 Cu1 167.54(18) . . ? N1 C111 O111 178.0(2) . . ? C2 O1 Cu1 125.71(14) . . ? O1 C2 C3 125.0(2) . . ? O1 C2 C12 114.81(18) . . ? C3 C2 C12 120.19(19) . . ? C2 C3 C4 126.0(2) . . ? C2 C3 H3 117.0 . . ? C4 C3 H3 117.0 . . ? N5 C4 C3 122.54(19) . . ? N5 C4 C11 120.68(19) . . ? C3 C4 C11 116.78(19) . . ? C4 N5 C6 120.02(18) . . ? C4 N5 Cu1 126.26(15) . . ? C6 N5 Cu1 113.71(14) . . ? N5 C6 C7 106.83(17) . . ? N5 C6 H6A 110.4 . . ? C7 C6 H6A 110.4 . . ? N5 C6 H6B 110.4 . . ? C7 C6 H6B 110.4 . . ? H6A C6 H6B 108.6 . . ? N8 C7 C6 110.27(17) . . ? N8 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? N8 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C10 N8 C9 108.72(18) . . ? C10 N8 C7 111.54(17) . . ? C9 N8 C7 109.45(17) . . ? C10 N8 Cu1 109.45(14) . . ? C9 N8 Cu1 114.65(13) . . ? C7 N8 Cu1 102.97(13) . . ? N8 C9 H9A 109.5 . . ? N8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N8 C10 H10A 109.5 . . ? N8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 117.98(19) . . ? C17 C12 C2 118.69(19) . . ? C13 C12 C2 123.32(19) . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 120.8(2) . . ? C13 C14 H14 119.6 . . ? C15 C14 H14 119.6 . . ? C16 C15 C14 118.9(2) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C17 C16 C15 120.5(2) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C12 121.2(2) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? 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 O1 Cu1 N1 C111 111.9(8) . . . . ? N5 Cu1 N1 C111 3.5(10) . . . . ? N8 Cu1 N1 C111 -67.1(8) . . . . ? Cu1 N1 C111 O111 -171(6) . . . . ? N1 Cu1 O1 C2 -177.37(17) . . . . ? N5 Cu1 O1 C2 -9.78(17) . . . . ? N8 Cu1 O1 C2 -38(2) . . . . ? Cu1 O1 C2 C3 10.1(3) . . . . ? Cu1 O1 C2 C12 -170.09(13) . . . . ? O1 C2 C3 C4 -0.9(3) . . . . ? C12 C2 C3 C4 179.32(19) . . . . ? C2 C3 C4 N5 -6.6(3) . . . . ? C2 C3 C4 C11 173.4(2) . . . . ? C3 C4 N5 C6 -176.74(18) . . . . ? C11 C4 N5 C6 3.3(3) . . . . ? C3 C4 N5 Cu1 3.8(3) . . . . ? C11 C4 N5 Cu1 -176.13(15) . . . . ? O1 Cu1 N5 C4 2.95(17) . . . . ? N1 Cu1 N5 C4 111.0(3) . . . . ? N8 Cu1 N5 C4 -177.83(17) . . . . ? O1 Cu1 N5 C6 -176.54(14) . . . . ? N1 Cu1 N5 C6 -68.5(4) . . . . ? N8 Cu1 N5 C6 2.69(14) . . . . ? C4 N5 C6 C7 152.60(18) . . . . ? Cu1 N5 C6 C7 -27.9(2) . . . . ? N5 C6 C7 N8 49.4(2) . . . . ? C6 C7 N8 C10 72.1(2) . . . . ? C6 C7 N8 C9 -167.52(17) . . . . ? C6 C7 N8 Cu1 -45.15(18) . . . . ? O1 Cu1 N8 C10 -67(2) . . . . ? N1 Cu1 N8 C10 72.19(15) . . . . ? N5 Cu1 N8 C10 -95.46(15) . . . . ? O1 Cu1 N8 C9 171(2) . . . . ? N1 Cu1 N8 C9 -50.26(15) . . . . ? N5 Cu1 N8 C9 142.09(15) . . . . ? O1 Cu1 N8 C7 52(2) . . . . ? N1 Cu1 N8 C7 -169.06(13) . . . . ? N5 Cu1 N8 C7 23.29(13) . . . . ? O1 C2 C12 C17 10.5(3) . . . . ? C3 C2 C12 C17 -169.72(19) . . . . ? O1 C2 C12 C13 -170.73(19) . . . . ? C3 C2 C12 C13 9.1(3) . . . . ? C17 C12 C13 C14 1.0(3) . . . . ? C2 C12 C13 C14 -177.84(19) . . . . ? C12 C13 C14 C15 0.1(3) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C17 -0.5(3) . . . . ? C15 C16 C17 C12 1.6(3) . . . . ? C13 C12 C17 C16 -1.9(3) . . . . ? C2 C12 C17 C16 177.00(19) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.307 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.076 data_sm56a _database_code_depnum_ccdc_archive 'CCDC 248272' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 Cu N3 O S' _chemical_formula_weight 352.93 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' 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' S S 0.1246 0.1234 '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' _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 11.1950(10) _cell_length_b 8.302(3) _cell_length_c 17.262(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.140(10) _cell_angle_gamma 90.00 _cell_volume 1604.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 30 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 18.49 _exptl_crystal_description Plate _exptl_crystal_colour Blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.461 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 1.493 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.5412 _exptl_absorpt_correction_T_max 0.5976 _exptl_absorpt_process_details 'North et al., 1968' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3787 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0586 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2829 _reflns_number_gt 2391 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0413P)^2^+0.8198P] 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 2829 _refine_ls_number_parameters 193 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0922 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.001 _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 0.66455(3) 0.16908(4) 0.624650(17) 0.01356(13) Uani 1 1 d . . . O1 O 0.50667(17) 0.2409(3) 0.64819(10) 0.0180(4) Uani 1 1 d . . . N1 N 0.6862(2) 0.0999(3) 0.73222(14) 0.0215(6) Uani 1 1 d . . . S1 S 0.73985(7) -0.01878(9) 0.88049(4) 0.01891(19) Uani 1 1 d . . . C111 C 0.7078(2) 0.0485(3) 0.79353(15) 0.0146(6) Uani 1 1 d . . . C1 C 0.4312(2) 0.2999(3) 0.59845(15) 0.0141(6) Uani 1 1 d . . . C2 C 0.3247(3) 0.3810(3) 0.63271(15) 0.0137(6) Uani 1 1 d . . . C3 C 0.3316(3) 0.4319(4) 0.70996(15) 0.0172(6) Uani 1 1 d . . . H3 H 0.4006 0.4119 0.7393 0.021 Uiso 1 1 calc R . . C4 C 0.2369(3) 0.5118(4) 0.74322(17) 0.0225(7) Uani 1 1 d . . . H4 H 0.2438 0.5465 0.7943 0.027 Uiso 1 1 calc R . . C5 C 0.1324(3) 0.5408(4) 0.70157(17) 0.0236(7) Uani 1 1 d . . . H5 H 0.0690 0.5940 0.7244 0.028 Uiso 1 1 calc R . . C6 C 0.1235(3) 0.4889(4) 0.62477(18) 0.0222(7) Uani 1 1 d . . . H6 H 0.0534 0.5071 0.5963 0.027 Uiso 1 1 calc R . . C7 C 0.2183(3) 0.4105(4) 0.59054(16) 0.0179(6) Uani 1 1 d . . . H7 H 0.2113 0.3772 0.5392 0.022 Uiso 1 1 calc R . . C8 C 0.4423(2) 0.2945(3) 0.51854(16) 0.0144(6) Uani 1 1 d . . . H8 H 0.3803 0.3390 0.4889 0.017 Uiso 1 1 calc R . . C9 C 0.5394(3) 0.2273(3) 0.47773(15) 0.0141(6) Uani 1 1 d . . . C10 C 0.5266(3) 0.2187(4) 0.39078(15) 0.0186(6) Uani 1 1 d . . . H10A H 0.5881 0.2820 0.3676 0.028 Uiso 1 1 calc R . . H10B H 0.4498 0.2599 0.3750 0.028 Uiso 1 1 calc R . . H10C H 0.5336 0.1087 0.3743 0.028 Uiso 1 1 calc R . . N10 N 0.6374(2) 0.1762(3) 0.51312(12) 0.0133(5) Uani 1 1 d . . . C11 C 0.7361(3) 0.1121(4) 0.46800(15) 0.0175(6) Uani 1 1 d . . . H11A H 0.7434 0.1717 0.4200 0.021 Uiso 1 1 calc R . . H11B H 0.7220 -0.0003 0.4555 0.021 Uiso 1 1 calc R . . C12 C 0.8498(3) 0.1293(4) 0.51732(15) 0.0179(6) Uani 1 1 d . . . H12A H 0.9134 0.0669 0.4946 0.021 Uiso 1 1 calc R . . H12B H 0.8744 0.2414 0.5185 0.021 Uiso 1 1 calc R . . C13 C 0.8182(3) -0.1050(4) 0.59996(18) 0.0223(7) Uani 1 1 d . . . H13A H 0.8899 -0.1533 0.5810 0.033 Uiso 1 1 calc R . . H13B H 0.7514 -0.1381 0.5681 0.033 Uiso 1 1 calc R . . H13C H 0.8062 -0.1388 0.6524 0.033 Uiso 1 1 calc R . . N13 N 0.8295(2) 0.0726(3) 0.59732(13) 0.0156(5) Uani 1 1 d . . . C14 C 0.9314(3) 0.1206(4) 0.64832(17) 0.0212(6) Uani 1 1 d . . . H14A H 1.0037 0.0742 0.6293 0.032 Uiso 1 1 calc R . . H14B H 0.9183 0.0827 0.7000 0.032 Uiso 1 1 calc R . . H14C H 0.9384 0.2358 0.6487 0.032 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 0.0138(2) 0.0169(2) 0.01005(18) 0.00138(13) 0.00157(12) 0.00296(14) O1 0.0169(10) 0.0257(12) 0.0114(9) 0.0024(8) 0.0023(8) 0.0056(9) N1 0.0207(13) 0.0273(15) 0.0165(12) 0.0035(11) 0.0012(10) 0.0058(11) S1 0.0300(4) 0.0145(4) 0.0121(3) 0.0012(3) -0.0034(3) -0.0007(3) C111 0.0114(13) 0.0158(14) 0.0166(14) -0.0022(12) 0.0022(11) 0.0022(11) C1 0.0140(14) 0.0129(14) 0.0154(13) 0.0000(11) 0.0005(11) -0.0025(11) C2 0.0150(14) 0.0105(13) 0.0158(13) 0.0008(11) 0.0045(11) -0.0025(11) C3 0.0202(15) 0.0159(15) 0.0156(13) 0.0026(12) 0.0024(12) -0.0019(12) C4 0.0296(17) 0.0200(16) 0.0181(14) -0.0015(12) 0.0100(12) 0.0029(14) C5 0.0268(16) 0.0177(15) 0.0270(15) 0.0029(13) 0.0166(13) 0.0020(13) C6 0.0149(14) 0.0199(16) 0.0319(16) 0.0016(13) 0.0013(12) 0.0011(12) C7 0.0172(14) 0.0194(15) 0.0172(13) -0.0006(12) 0.0031(11) -0.0014(12) C8 0.0132(13) 0.0156(14) 0.0142(12) -0.0001(11) -0.0023(10) 0.0008(11) C9 0.0178(14) 0.0116(13) 0.0129(13) 0.0022(11) 0.0010(11) -0.0045(11) C10 0.0184(15) 0.0257(16) 0.0119(13) 0.0000(12) 0.0014(11) 0.0039(13) N10 0.0127(11) 0.0158(12) 0.0115(10) -0.0018(9) 0.0026(9) -0.0003(10) C11 0.0173(15) 0.0195(15) 0.0159(13) 0.0001(12) 0.0043(11) 0.0036(12) C12 0.0180(15) 0.0187(15) 0.0170(13) 0.0017(12) 0.0046(11) 0.0027(12) C13 0.0255(17) 0.0142(15) 0.0274(15) 0.0012(13) 0.0034(13) 0.0028(13) N13 0.0161(12) 0.0138(13) 0.0170(11) 0.0007(10) 0.0013(10) 0.0018(10) C14 0.0163(15) 0.0227(16) 0.0244(15) 0.0019(13) -0.0020(12) 0.0027(12) _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 O1 1.9166(19) . ? Cu1 N10 1.944(2) . ? Cu1 N1 1.954(2) . ? Cu1 N13 2.076(2) . ? Cu1 S1 2.8058(12) 2_656 ? O1 C1 1.289(3) . ? N1 C111 1.162(4) . ? S1 C111 1.635(3) . ? S1 Cu1 2.8058(12) 2_646 ? C1 C8 1.388(4) . ? C1 C2 1.501(4) . ? C2 C3 1.400(4) . ? C2 C7 1.406(4) . ? C3 C4 1.385(4) . ? C3 H3 0.9300 . ? C4 C5 1.382(5) . ? C4 H4 0.9300 . ? C5 C6 1.396(4) . ? C5 H5 0.9300 . ? C6 C7 1.387(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.422(4) . ? C8 H8 0.9300 . ? C9 N10 1.314(4) . ? C9 C10 1.507(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? N10 C11 1.466(3) . ? C11 C12 1.524(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 N13 1.481(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 N13 1.481(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? N13 C14 1.482(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N10 94.22(9) . . ? O1 Cu1 N1 89.28(9) . . ? N10 Cu1 N1 164.57(11) . . ? O1 Cu1 N13 175.25(10) . . ? N10 Cu1 N13 84.79(9) . . ? N1 Cu1 N13 90.48(10) . . ? O1 Cu1 S1 94.20(7) . 2_656 ? N10 Cu1 S1 89.59(7) . 2_656 ? N1 Cu1 S1 105.15(9) . 2_656 ? N13 Cu1 S1 90.44(7) . 2_656 ? C1 O1 Cu1 124.88(17) . . ? C111 N1 Cu1 173.2(2) . . ? C111 S1 Cu1 111.31(10) . 2_646 ? N1 C111 S1 178.4(3) . . ? O1 C1 C8 125.4(3) . . ? O1 C1 C2 115.0(2) . . ? C8 C1 C2 119.6(2) . . ? C3 C2 C7 118.1(3) . . ? C3 C2 C1 118.8(2) . . ? C7 C2 C1 123.1(2) . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 121.0(3) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 119.0(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C7 C6 C5 120.6(3) . . ? C7 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? C6 C7 C2 120.6(3) . . ? C6 C7 H7 119.7 . . ? C2 C7 H7 119.7 . . ? C1 C8 C9 126.1(3) . . ? C1 C8 H8 116.9 . . ? C9 C8 H8 116.9 . . ? N10 C9 C8 122.4(2) . . ? N10 C9 C10 120.7(3) . . ? C8 C9 C10 116.9(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 N10 C11 120.1(2) . . ? C9 N10 Cu1 125.64(19) . . ? C11 N10 Cu1 114.22(17) . . ? N10 C11 C12 107.4(2) . . ? N10 C11 H11A 110.2 . . ? C12 C11 H11A 110.2 . . ? N10 C11 H11B 110.2 . . ? C12 C11 H11B 110.2 . . ? H11A C11 H11B 108.5 . . ? N13 C12 C11 110.4(2) . . ? N13 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? N13 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? N13 C13 H13A 109.5 . . ? N13 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N13 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C13 N13 C12 111.1(2) . . ? C13 N13 C14 108.3(2) . . ? C12 N13 C14 109.7(2) . . ? C13 N13 Cu1 107.50(19) . . ? C12 N13 Cu1 104.06(17) . . ? C14 N13 Cu1 116.06(18) . . ? N13 C14 H14A 109.5 . . ? N13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 N10 Cu1 O1 C1 -11.8(2) . . . . ? N1 Cu1 O1 C1 -176.7(2) . . . . ? N13 Cu1 O1 C1 -89.5(10) . . . . ? S1 Cu1 O1 C1 78.1(2) 2_656 . . . ? O1 Cu1 N1 C111 158(2) . . . . ? N10 Cu1 N1 C111 54(2) . . . . ? N13 Cu1 N1 C111 -18(2) . . . . ? S1 Cu1 N1 C111 -108(2) 2_656 . . . ? Cu1 N1 C111 S1 110(9) . . . . ? Cu1 S1 C111 N1 -136(9) 2_646 . . . ? Cu1 O1 C1 C8 12.4(4) . . . . ? Cu1 O1 C1 C2 -167.01(18) . . . . ? O1 C1 C2 C3 19.8(4) . . . . ? C8 C1 C2 C3 -159.6(3) . . . . ? O1 C1 C2 C7 -161.0(3) . . . . ? C8 C1 C2 C7 19.5(4) . . . . ? C7 C2 C3 C4 -1.2(4) . . . . ? C1 C2 C3 C4 178.0(3) . . . . ? C2 C3 C4 C5 1.2(5) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C4 C5 C6 C7 -0.5(5) . . . . ? C5 C6 C7 C2 0.4(5) . . . . ? C3 C2 C7 C6 0.4(4) . . . . ? C1 C2 C7 C6 -178.7(3) . . . . ? O1 C1 C8 C9 -1.7(5) . . . . ? C2 C1 C8 C9 177.7(3) . . . . ? C1 C8 C9 N10 -7.2(5) . . . . ? C1 C8 C9 C10 173.6(3) . . . . ? C8 C9 N10 C11 -178.3(3) . . . . ? C10 C9 N10 C11 0.8(4) . . . . ? C8 C9 N10 Cu1 4.1(4) . . . . ? C10 C9 N10 Cu1 -176.7(2) . . . . ? O1 Cu1 N10 C9 3.7(2) . . . . ? N1 Cu1 N10 C9 106.4(4) . . . . ? N13 Cu1 N10 C9 179.1(2) . . . . ? S1 Cu1 N10 C9 -90.5(2) 2_656 . . . ? O1 Cu1 N10 C11 -174.0(2) . . . . ? N1 Cu1 N10 C11 -71.3(4) . . . . ? N13 Cu1 N10 C11 1.4(2) . . . . ? S1 Cu1 N10 C11 91.85(19) 2_656 . . . ? C9 N10 C11 C12 156.8(3) . . . . ? Cu1 N10 C11 C12 -25.4(3) . . . . ? N10 C11 C12 N13 46.5(3) . . . . ? C11 C12 N13 C13 71.8(3) . . . . ? C11 C12 N13 C14 -168.4(2) . . . . ? C11 C12 N13 Cu1 -43.6(3) . . . . ? O1 Cu1 N13 C13 -16.5(11) . . . . ? N10 Cu1 N13 C13 -94.61(19) . . . . ? N1 Cu1 N13 C13 70.7(2) . . . . ? S1 Cu1 N13 C13 175.84(18) 2_656 . . . ? O1 Cu1 N13 C12 101.5(10) . . . . ? N10 Cu1 N13 C12 23.32(18) . . . . ? N1 Cu1 N13 C12 -171.39(19) . . . . ? S1 Cu1 N13 C12 -66.23(17) 2_656 . . . ? O1 Cu1 N13 C14 -137.9(9) . . . . ? N10 Cu1 N13 C14 144.0(2) . . . . ? N1 Cu1 N13 C14 -50.7(2) . . . . ? S1 Cu1 N13 C14 54.43(19) 2_656 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.579 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.086 data_sm55a _database_code_depnum_ccdc_archive 'CCDC 248273' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H19 Cu N5 O' _chemical_formula_sum 'C14 H19 Cu N5 O' _chemical_formula_weight 336.88 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 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 19.392(3) _cell_length_b 11.762(2) _cell_length_c 13.203(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.012(6) _cell_angle_gamma 90.00 _cell_volume 3007.4(8) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4594 _cell_measurement_theta_min 2.515 _cell_measurement_theta_max 27.169 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.459 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.446 _exptl_absorpt_correction_T_max 0.768 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'BrukerNonius X8Apex' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 24667 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_sigmaI/netI 0.0775 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 29.73 _reflns_number_total 8340 _reflns_number_gt 6167 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'BrukerNonius Apex2' _computing_cell_refinement 'BrukerNonius Apex2' _computing_data_reduction 'BrukerNonius Apex2' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0715P)^2^+20.5547P] 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 8340 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1478 _refine_ls_R_factor_gt 0.1221 _refine_ls_wR_factor_ref 0.3149 _refine_ls_wR_factor_gt 0.3080 _refine_ls_goodness_of_fit_ref 1.660 _refine_ls_restrained_S_all 1.660 _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 0.23342(6) 0.47756(9) 0.22505(8) 0.0215(3) Uani 1 1 d . . . O1 O 0.1713(3) 0.3909(5) 0.1383(4) 0.0239(12) Uani 1 1 d . . . N1 N 0.3126(4) 0.3907(8) 0.1745(7) 0.0361(19) Uani 1 1 d . . . N2 N 0.3005(4) 0.3080(7) 0.1244(6) 0.0274(16) Uani 1 1 d . . . N3 N 0.2933(4) 0.2273(7) 0.0748(7) 0.0336(18) Uani 1 1 d . . . C2 C 0.1058(5) 0.4047(6) 0.1275(6) 0.0198(16) Uani 1 1 d . . . C3 C 0.0675(4) 0.4812(7) 0.1819(6) 0.0229(16) Uani 1 1 d . . . H3 H 0.0197 0.4873 0.1632 0.027 Uiso 1 1 calc R . . C4 C 0.0936(5) 0.5513(7) 0.2630(6) 0.0211(16) Uani 1 1 d . . . N5 N 0.1594(4) 0.5561(6) 0.2915(5) 0.0190(13) Uani 1 1 d . . . C6 C 0.1838(5) 0.6231(8) 0.3821(6) 0.029(2) Uani 1 1 d . . . H6A H 0.1559 0.6933 0.3867 0.035 Uiso 1 1 calc R . . H6B H 0.1782 0.5779 0.4444 0.035 Uiso 1 1 calc R . . C7 C 0.2574(6) 0.6530(7) 0.3733(7) 0.031(2) Uani 1 1 d . . . H7A H 0.2776 0.6753 0.4408 0.038 Uiso 1 1 calc R . . H7B H 0.2609 0.7188 0.3272 0.038 Uiso 1 1 calc R . . N8 N 0.2983(4) 0.5534(6) 0.3327(5) 0.0213(14) Uani 1 1 d . . . C9 C 0.3643(5) 0.5946(9) 0.2979(8) 0.036(2) Uani 1 1 d . . . H9A H 0.3920 0.6260 0.3555 0.055 Uiso 1 1 calc R . . H9B H 0.3558 0.6539 0.2466 0.055 Uiso 1 1 calc R . . H9C H 0.3894 0.5314 0.2683 0.055 Uiso 1 1 calc R . . C10 C 0.3102(6) 0.4659(8) 0.4136(7) 0.035(2) Uani 1 1 d . . . H10A H 0.3399 0.4055 0.3890 0.052 Uiso 1 1 calc R . . H10B H 0.2658 0.4333 0.4310 0.052 Uiso 1 1 calc R . . H10C H 0.3326 0.5013 0.4739 0.052 Uiso 1 1 calc R . . C11 C 0.0418(5) 0.6224(8) 0.3167(8) 0.033(2) Uani 1 1 d . . . H11A H 0.0400 0.5968 0.3872 0.050 Uiso 1 1 calc R . . H11B H -0.0039 0.6140 0.2823 0.050 Uiso 1 1 calc R . . H11C H 0.0558 0.7024 0.3156 0.050 Uiso 1 1 calc R . . C12 C 0.0705(4) 0.3279(6) 0.0499(5) 0.0189(15) Uani 1 1 d . . . C13 C 0.1080(5) 0.2363(7) 0.0125(6) 0.0248(17) Uani 1 1 d . . . H13 H 0.1545 0.2241 0.0360 0.030 Uiso 1 1 calc R . . C14 C 0.0766(5) 0.1634(8) -0.0593(6) 0.0289(19) Uani 1 1 d . . . H14 H 0.1024 0.1020 -0.0849 0.035 Uiso 1 1 calc R . . C15 C 0.0088(5) 0.1785(8) -0.0939(7) 0.031(2) Uani 1 1 d . . . H15 H -0.0118 0.1280 -0.1428 0.037 Uiso 1 1 calc R . . C16 C -0.0285(5) 0.2668(7) -0.0573(7) 0.0260(18) Uani 1 1 d . . . H16 H -0.0754 0.2768 -0.0802 0.031 Uiso 1 1 calc R . . C17 C 0.0018(5) 0.3427(7) 0.0139(6) 0.0225(17) Uani 1 1 d . . . H17 H -0.0243 0.4045 0.0378 0.027 Uiso 1 1 calc R . . Cu1A Cu 0.26971(5) 0.93571(8) 0.22443(7) 0.0185(2) Uani 1 1 d . . . O1A O 0.3341(3) 0.8538(5) 0.1475(5) 0.0246(13) Uani 1 1 d . . . N1A N 0.1948(4) 0.8351(6) 0.1694(5) 0.0258(15) Uani 1 1 d . . . C2A C 0.3973(4) 0.8809(6) 0.1344(5) 0.0179(15) Uani 1 1 d . . . N2A N 0.2098(4) 0.7473(6) 0.1281(5) 0.0246(15) Uani 1 1 d . . . C3A C 0.4308(5) 0.9743(7) 0.1775(6) 0.0217(16) Uani 1 1 d . . . H3A H 0.4772 0.9869 0.1608 0.026 Uiso 1 1 calc R . . N3A N 0.2230(5) 0.6608(7) 0.0907(7) 0.0355(19) Uani 1 1 d . . . C4A C 0.4015(4) 1.0530(6) 0.2449(6) 0.0188(15) Uani 1 1 d . . . N5A N 0.3380(4) 1.0423(6) 0.2775(5) 0.0226(15) Uani 1 1 d . . . C6A C 0.3119(5) 1.1269(7) 0.3463(7) 0.0282(19) Uani 1 1 d . . . H6A1 H 0.2999 1.1979 0.3092 0.034 Uiso 1 1 calc R . . H6A2 H 0.3472 1.1446 0.4009 0.034 Uiso 1 1 calc R . . C7A C 0.2477(5) 1.0764(8) 0.3912(6) 0.0289(19) Uani 1 1 d . . . H7A1 H 0.2617 1.0182 0.4425 0.035 Uiso 1 1 calc R . . H7A2 H 0.2221 1.1369 0.4254 0.035 Uiso 1 1 calc R . . N8A N 0.2023(4) 1.0241(6) 0.3111(5) 0.0181(13) Uani 1 1 d . . . C9A C 0.1481(5) 0.9570(8) 0.3577(7) 0.032(2) Uani 1 1 d . . . H9A1 H 0.1697 0.8998 0.4032 0.048 Uiso 1 1 calc R . . H9A2 H 0.1195 0.9190 0.3045 0.048 Uiso 1 1 calc R . . H9A3 H 0.1192 1.0076 0.3965 0.048 Uiso 1 1 calc R . . C10A C 0.1686(5) 1.1111(8) 0.2418(8) 0.035(2) Uani 1 1 d . . . H10D H 0.1374 1.1581 0.2801 0.053 Uiso 1 1 calc R . . H10E H 0.1423 1.0726 0.1864 0.053 Uiso 1 1 calc R . . H10F H 0.2041 1.1593 0.2138 0.053 Uiso 1 1 calc R . . C11A C 0.4472(5) 1.1485(8) 0.2854(7) 0.0285(19) Uani 1 1 d . . . H11D H 0.4223 1.2207 0.2782 0.043 Uiso 1 1 calc R . . H11E H 0.4891 1.1518 0.2471 0.043 Uiso 1 1 calc R . . H11F H 0.4599 1.1348 0.3572 0.043 Uiso 1 1 calc R . . C12A C 0.4347(4) 0.8055(7) 0.0624(6) 0.0208(16) Uani 1 1 d . . . C13A C 0.4983(5) 0.8332(7) 0.0242(6) 0.0258(18) Uani 1 1 d . . . H13A H 0.5202 0.9026 0.0438 0.031 Uiso 1 1 calc R . . C14A C 0.5304(5) 0.7600(9) -0.0426(7) 0.030(2) Uani 1 1 d . . . H14A H 0.5732 0.7806 -0.0694 0.036 Uiso 1 1 calc R . . C15A C 0.4993(5) 0.6576(8) -0.0692(6) 0.031(2) Uani 1 1 d . . . H15A H 0.5219 0.6067 -0.1124 0.037 Uiso 1 1 calc R . . C16A C 0.4356(5) 0.6283(8) -0.0336(6) 0.0281(19) Uani 1 1 d . . . H16A H 0.4141 0.5590 -0.0547 0.034 Uiso 1 1 calc R . . C17A C 0.4029(5) 0.7006(7) 0.0333(6) 0.0234(17) Uani 1 1 d . . . H17A H 0.3598 0.6798 0.0590 0.028 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 0.0266(5) 0.0187(5) 0.0191(5) -0.0038(4) 0.0002(4) -0.0022(4) O1 0.030(3) 0.021(3) 0.021(3) -0.007(2) 0.001(2) -0.003(2) N1 0.032(4) 0.036(5) 0.040(5) -0.015(4) -0.001(4) 0.001(4) N2 0.026(4) 0.029(4) 0.027(4) 0.004(3) 0.004(3) 0.005(3) N3 0.038(5) 0.024(4) 0.039(5) -0.009(3) 0.002(4) 0.001(3) C2 0.038(5) 0.010(3) 0.012(3) 0.002(3) 0.000(3) -0.002(3) C3 0.023(4) 0.020(4) 0.026(4) -0.006(3) -0.002(3) 0.002(3) C4 0.036(5) 0.013(4) 0.014(3) 0.004(3) 0.005(3) 0.001(3) N5 0.029(4) 0.012(3) 0.016(3) -0.003(2) 0.001(3) 0.001(3) C6 0.038(5) 0.029(5) 0.020(4) -0.014(3) -0.002(3) -0.001(4) C7 0.057(6) 0.016(4) 0.021(4) -0.004(3) -0.003(4) 0.000(4) N8 0.028(4) 0.012(3) 0.024(3) -0.003(3) 0.000(3) -0.003(3) C9 0.040(6) 0.037(5) 0.033(5) -0.017(4) 0.005(4) -0.010(4) C10 0.056(6) 0.024(5) 0.023(4) -0.001(3) -0.006(4) 0.000(4) C11 0.041(6) 0.022(4) 0.036(5) -0.012(4) 0.005(4) 0.003(4) C12 0.033(4) 0.012(3) 0.012(3) -0.004(3) 0.003(3) -0.004(3) C13 0.031(5) 0.017(4) 0.026(4) -0.002(3) -0.002(3) 0.000(3) C14 0.047(6) 0.022(4) 0.018(4) -0.009(3) -0.001(4) 0.002(4) C15 0.040(5) 0.021(4) 0.032(5) -0.009(4) 0.000(4) -0.003(4) C16 0.030(5) 0.022(4) 0.026(4) 0.001(3) -0.005(3) -0.002(3) C17 0.032(5) 0.010(3) 0.026(4) 0.001(3) 0.005(3) -0.001(3) Cu1A 0.0252(5) 0.0111(4) 0.0191(5) -0.0024(4) 0.0010(4) -0.0001(4) O1A 0.027(3) 0.015(3) 0.032(3) -0.009(2) 0.006(2) -0.003(2) N1A 0.030(4) 0.025(4) 0.023(3) -0.012(3) -0.001(3) -0.002(3) C2A 0.030(4) 0.012(3) 0.012(3) -0.001(3) 0.002(3) 0.001(3) N2A 0.031(4) 0.020(4) 0.022(3) -0.001(3) -0.001(3) -0.003(3) C3A 0.029(4) 0.018(4) 0.019(4) -0.005(3) 0.011(3) -0.002(3) N3A 0.046(5) 0.023(4) 0.039(4) -0.015(3) 0.012(4) -0.008(4) C4A 0.028(4) 0.012(3) 0.016(3) -0.003(3) 0.000(3) -0.004(3) N5A 0.033(4) 0.013(3) 0.021(3) -0.006(3) 0.000(3) 0.002(3) C6A 0.038(5) 0.018(4) 0.029(4) -0.011(3) 0.002(4) -0.003(4) C7A 0.043(5) 0.026(5) 0.018(4) -0.007(3) 0.005(4) -0.005(4) N8A 0.029(4) 0.014(3) 0.012(3) -0.003(2) 0.003(2) 0.004(3) C9A 0.046(6) 0.031(5) 0.020(4) 0.006(3) 0.011(4) -0.008(4) C10A 0.036(5) 0.023(4) 0.046(6) 0.006(4) -0.008(4) 0.008(4) C11A 0.037(5) 0.024(4) 0.024(4) -0.001(3) 0.002(4) -0.009(4) C12A 0.032(4) 0.016(4) 0.015(3) -0.001(3) 0.000(3) 0.004(3) C13A 0.035(5) 0.017(4) 0.025(4) 0.006(3) -0.003(3) 0.000(3) C14A 0.033(5) 0.037(5) 0.021(4) 0.012(4) 0.002(3) 0.005(4) C15A 0.049(6) 0.023(4) 0.019(4) -0.002(3) 0.002(4) 0.013(4) C16A 0.042(5) 0.027(5) 0.015(4) -0.007(3) -0.002(3) 0.003(4) C17A 0.036(5) 0.021(4) 0.013(3) 0.003(3) 0.002(3) 0.000(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 O1 1.912(6) . ? Cu1 N5 1.954(7) . ? Cu1 N1 1.989(9) . ? Cu1 N8 2.052(7) . ? Cu1 N3A 2.792(9) . ? O1 C2 1.282(11) . ? N1 N2 1.192(11) . ? N2 N3 1.157(11) . ? C2 C3 1.390(12) . ? C2 C12 1.504(10) . ? C3 C4 1.423(11) . ? C3 H3 0.9500 . ? C4 N5 1.313(11) . ? C4 C11 1.511(12) . ? N5 C6 1.489(10) . ? C6 C7 1.481(14) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N8 1.528(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? N8 C9 1.465(12) . ? N8 C10 1.493(11) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C17 1.400(12) . ? C12 C13 1.403(12) . ? C13 C14 1.395(11) . ? C13 H13 0.9500 . ? C14 C15 1.380(14) . ? C14 H14 0.9500 . ? C15 C16 1.369(13) . ? C15 H15 0.9500 . ? C16 C17 1.402(12) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? Cu1A O1A 1.912(6) . ? Cu1A N5A 1.929(7) . ? Cu1A N1A 1.981(7) . ? Cu1A N8A 2.063(7) . ? O1A C2A 1.286(10) . ? N1A N2A 1.210(10) . ? C2A C3A 1.384(11) . ? C2A C12A 1.512(11) . ? N2A N3A 1.166(10) . ? C3A C4A 1.423(11) . ? C3A H3A 0.9500 . ? C4A N5A 1.331(11) . ? C4A C11A 1.510(11) . ? N5A C6A 1.456(10) . ? C6A C7A 1.527(13) . ? C6A H6A1 0.9900 . ? C6A H6A2 0.9900 . ? C7A N8A 1.474(10) . ? C7A H7A1 0.9900 . ? C7A H7A2 0.9900 . ? N8A C9A 1.475(11) . ? N8A C10A 1.499(11) . ? C9A H9A1 0.9800 . ? C9A H9A2 0.9800 . ? C9A H9A3 0.9800 . ? C10A H10D 0.9800 . ? C10A H10E 0.9800 . ? C10A H10F 0.9800 . ? C11A H11D 0.9800 . ? C11A H11E 0.9800 . ? C11A H11F 0.9800 . ? C12A C13A 1.395(13) . ? C12A C17A 1.423(11) . ? C13A C14A 1.401(13) . ? C13A H13A 0.9500 . ? C14A C15A 1.384(14) . ? C14A H14A 0.9500 . ? C15A C16A 1.388(14) . ? C15A H15A 0.9500 . ? C16A C17A 1.403(12) . ? C16A H16A 0.9500 . ? C17A H17A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N5 93.8(3) . . ? O1 Cu1 N1 89.9(3) . . ? N5 Cu1 N1 172.9(3) . . ? O1 Cu1 N8 172.1(3) . . ? N5 Cu1 N8 85.5(3) . . ? N1 Cu1 N8 90.0(3) . . ? C2 O1 Cu1 126.1(5) . . ? N2 N1 Cu1 118.2(7) . . ? N3 N2 N1 175.5(10) . . ? O1 C2 C3 125.3(7) . . ? O1 C2 C12 114.4(7) . . ? C3 C2 C12 120.3(8) . . ? C2 C3 C4 125.9(8) . . ? C2 C3 H3 117.1 . . ? C4 C3 H3 117.1 . . ? N5 C4 C3 122.8(8) . . ? N5 C4 C11 120.1(7) . . ? C3 C4 C11 117.1(8) . . ? C4 N5 C6 121.0(7) . . ? C4 N5 Cu1 125.3(5) . . ? C6 N5 Cu1 113.7(5) . . ? C7 C6 N5 109.2(7) . . ? C7 C6 H6A 109.8 . . ? N5 C6 H6A 109.8 . . ? C7 C6 H6B 109.8 . . ? N5 C6 H6B 109.8 . . ? H6A C6 H6B 108.3 . . ? C6 C7 N8 111.5(7) . . ? C6 C7 H7A 109.3 . . ? N8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? N8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 N8 C10 110.4(8) . . ? C9 N8 C7 109.6(7) . . ? C10 N8 C7 109.9(7) . . ? C9 N8 Cu1 116.2(5) . . ? C10 N8 Cu1 105.2(5) . . ? C7 N8 Cu1 105.4(5) . . ? N8 C9 H9A 109.5 . . ? N8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N8 C10 H10A 109.5 . . ? N8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C4 C11 H11A 109.5 . . ? C4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C17 C12 C13 118.5(7) . . ? C17 C12 C2 123.2(7) . . ? C13 C12 C2 118.4(8) . . ? C14 C13 C12 119.7(8) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 121.3(8) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C16 C15 C14 119.6(8) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.5(8) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C12 C17 C16 120.4(8) . . ? C12 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? O1A Cu1A N5A 93.8(3) . . ? O1A Cu1A N1A 89.5(3) . . ? N5A Cu1A N1A 176.0(3) . . ? O1A Cu1A N8A 178.3(3) . . ? N5A Cu1A N8A 85.1(3) . . ? N1A Cu1A N8A 91.8(3) . . ? C2A O1A Cu1A 126.8(5) . . ? N2A N1A Cu1A 119.1(6) . . ? O1A C2A C3A 124.9(7) . . ? O1A C2A C12A 115.5(7) . . ? C3A C2A C12A 119.5(8) . . ? N3A N2A N1A 177.7(9) . . ? C2A C3A C4A 125.4(8) . . ? C2A C3A H3A 117.3 . . ? C4A C3A H3A 117.3 . . ? N5A C4A C3A 123.1(7) . . ? N5A C4A C11A 119.4(7) . . ? C3A C4A C11A 117.4(8) . . ? C4A N5A C6A 119.7(7) . . ? C4A N5A Cu1A 125.0(5) . . ? C6A N5A Cu1A 114.5(6) . . ? N5A C6A C7A 107.1(7) . . ? N5A C6A H6A1 110.3 . . ? C7A C6A H6A1 110.3 . . ? N5A C6A H6A2 110.3 . . ? C7A C6A H6A2 110.3 . . ? H6A1 C6A H6A2 108.5 . . ? N8A C7A C6A 110.6(7) . . ? N8A C7A H7A1 109.5 . . ? C6A C7A H7A1 109.5 . . ? N8A C7A H7A2 109.5 . . ? C6A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 108.1 . . ? C7A N8A C9A 109.5(6) . . ? C7A N8A C10A 112.2(7) . . ? C9A N8A C10A 108.8(7) . . ? C7A N8A Cu1A 103.7(5) . . ? C9A N8A Cu1A 116.6(5) . . ? C10A N8A Cu1A 105.9(5) . . ? N8A C9A H9A1 109.5 . . ? N8A C9A H9A2 109.5 . . ? H9A1 C9A H9A2 109.5 . . ? N8A C9A H9A3 109.5 . . ? H9A1 C9A H9A3 109.5 . . ? H9A2 C9A H9A3 109.5 . . ? N8A C10A H10D 109.5 . . ? N8A C10A H10E 109.5 . . ? H10D C10A H10E 109.5 . . ? N8A C10A H10F 109.5 . . ? H10D C10A H10F 109.5 . . ? H10E C10A H10F 109.5 . . ? C4A C11A H11D 109.5 . . ? C4A C11A H11E 109.5 . . ? H11D C11A H11E 109.5 . . ? C4A C11A H11F 109.5 . . ? H11D C11A H11F 109.5 . . ? H11E C11A H11F 109.5 . . ? C13A C12A C17A 118.9(8) . . ? C13A C12A C2A 123.6(7) . . ? C17A C12A C2A 117.5(8) . . ? C12A C13A C14A 121.0(8) . . ? C12A C13A H13A 119.5 . . ? C14A C13A H13A 119.5 . . ? C15A C14A C13A 119.5(9) . . ? C15A C14A H14A 120.3 . . ? C13A C14A H14A 120.3 . . ? C14A C15A C16A 120.9(8) . . ? C14A C15A H15A 119.5 . . ? C16A C15A H15A 119.5 . . ? C15A C16A C17A 120.2(8) . . ? C15A C16A H16A 119.9 . . ? C17A C16A H16A 119.9 . . ? C16A C17A C12A 119.5(8) . . ? C16A C17A H17A 120.3 . . ? C12A C17A H17A 120.3 . . ? 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 N5 Cu1 O1 C2 8.9(7) . . . . ? N1 Cu1 O1 C2 -177.1(7) . . . . ? O1 Cu1 N1 N2 -11.0(8) . . . . ? N8 Cu1 N1 N2 161.2(8) . . . . ? Cu1 O1 C2 C3 -4.2(11) . . . . ? Cu1 O1 C2 C12 177.0(5) . . . . ? O1 C2 C3 C4 -4.5(14) . . . . ? C12 C2 C3 C4 174.2(7) . . . . ? C2 C3 C4 N5 4.5(13) . . . . ? C2 C3 C4 C11 -175.7(8) . . . . ? C3 C4 N5 C6 -174.9(8) . . . . ? C11 C4 N5 C6 5.4(12) . . . . ? C3 C4 N5 Cu1 3.8(11) . . . . ? C11 C4 N5 Cu1 -175.9(6) . . . . ? O1 Cu1 N5 C4 -8.7(7) . . . . ? N8 Cu1 N5 C4 179.2(7) . . . . ? O1 Cu1 N5 C6 170.1(6) . . . . ? N8 Cu1 N5 C6 -2.1(6) . . . . ? C4 N5 C6 C7 -157.1(8) . . . . ? Cu1 N5 C6 C7 24.1(9) . . . . ? N5 C6 C7 N8 -41.3(10) . . . . ? C6 C7 N8 C9 163.9(8) . . . . ? C6 C7 N8 C10 -74.6(9) . . . . ? C6 C7 N8 Cu1 38.2(8) . . . . ? N5 Cu1 N8 C9 -140.8(7) . . . . ? N1 Cu1 N8 C9 44.7(7) . . . . ? N5 Cu1 N8 C10 96.8(6) . . . . ? N1 Cu1 N8 C10 -77.7(6) . . . . ? N5 Cu1 N8 C7 -19.3(5) . . . . ? N1 Cu1 N8 C7 166.2(6) . . . . ? O1 C2 C12 C17 -168.4(7) . . . . ? C3 C2 C12 C17 12.7(12) . . . . ? O1 C2 C12 C13 12.2(10) . . . . ? C3 C2 C12 C13 -166.7(8) . . . . ? C17 C12 C13 C14 0.4(12) . . . . ? C2 C12 C13 C14 179.8(8) . . . . ? C12 C13 C14 C15 -0.7(14) . . . . ? C13 C14 C15 C16 0.0(15) . . . . ? C14 C15 C16 C17 0.9(14) . . . . ? C13 C12 C17 C16 0.5(12) . . . . ? C2 C12 C17 C16 -178.9(7) . . . . ? C15 C16 C17 C12 -1.2(13) . . . . ? N5A Cu1A O1A C2A -7.0(7) . . . . ? N1A Cu1A O1A C2A 170.6(7) . . . . ? O1A Cu1A N1A N2A 14.9(7) . . . . ? N8A Cu1A N1A N2A -163.9(7) . . . . ? Cu1A O1A C2A C3A 2.2(12) . . . . ? Cu1A O1A C2A C12A -175.0(5) . . . . ? O1A C2A C3A C4A 1.8(14) . . . . ? C12A C2A C3A C4A 178.9(7) . . . . ? C2A C3A C4A N5A 2.8(13) . . . . ? C2A C3A C4A C11A 178.9(8) . . . . ? C3A C4A N5A C6A -179.9(8) . . . . ? C11A C4A N5A C6A 4.0(12) . . . . ? C3A C4A N5A Cu1A -10.5(11) . . . . ? C11A C4A N5A Cu1A 173.5(6) . . . . ? O1A Cu1A N5A C4A 10.9(7) . . . . ? N8A Cu1A N5A C4A -170.3(7) . . . . ? O1A Cu1A N5A C6A -179.2(6) . . . . ? N8A Cu1A N5A C6A -0.4(6) . . . . ? C4A N5A C6A C7A -165.3(7) . . . . ? Cu1A N5A C6A C7A 24.2(9) . . . . ? N5A C6A C7A N8A -46.0(10) . . . . ? C6A C7A N8A C9A 169.1(8) . . . . ? C6A C7A N8A C10A -70.0(10) . . . . ? C6A C7A N8A Cu1A 43.9(8) . . . . ? N5A Cu1A N8A C7A -24.1(5) . . . . ? N1A Cu1A N8A C7A 158.4(5) . . . . ? N5A Cu1A N8A C9A -144.6(6) . . . . ? N1A Cu1A N8A C9A 37.9(6) . . . . ? N5A Cu1A N8A C10A 94.2(6) . . . . ? N1A Cu1A N8A C10A -83.3(6) . . . . ? O1A C2A C12A C13A 167.6(7) . . . . ? C3A C2A C12A C13A -9.9(12) . . . . ? O1A C2A C12A C17A -12.9(10) . . . . ? C3A C2A C12A C17A 169.7(7) . . . . ? C17A C12A C13A C14A 0.6(12) . . . . ? C2A C12A C13A C14A -179.8(7) . . . . ? C12A C13A C14A C15A -1.5(12) . . . . ? C13A C14A C15A C16A 2.4(13) . . . . ? C14A C15A C16A C17A -2.4(13) . . . . ? C15A C16A C17A C12A 1.5(12) . . . . ? C13A C12A C17A C16A -0.6(12) . . . . ? C2A C12A C17A C16A 179.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.313 _refine_diff_density_min -1.817 _refine_diff_density_rms 0.208