Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2001 data_GLOBAL _journal_coden_Cambridge 182 # SUBMISSION DETAILS # Dioxygen activation by a neutral beta-diketiminato copper(I) ethylene complex # Manuscript file: warren.pdf # Electronic Supplementary Information file: warren-ESI.doc _publ_contact_author_name 'Warren, Timothy H.' _publ_contact_author_address ; Georgetown University Department of Chemistry Box 571227 Washington, DC 20057-1227 USA ; _publ_contact_author_phone '001 202 687 6362' _publ_contact_author_fax '001 202 687 6209' _publ_contact_author_email 'thw@georgetown.edu' _publ_requested_journal 'Chemical Communications' #======================================================================== # Title and Author List _publ_section_title ; Dioxygen activation by a neutral beta-diketiminato copper(I) ethylene complex ; loop_ _publ_author_name _publ_author_address 'Dai, Xuliang' ; Georgetown University Department of Chemistry Box 571227 Washington, DC 20057-1227 USA ; 'Warren, Timothy H.' ; Georgetown University Department of Chemistry Box 571227 Washington, DC 20057-1227 USA ; #======================================================================== data_41 _database_code_CSD 168944 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Me2NN]Cu(ethylene) + 0.5 pentane' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25.50 H35 Cu N2' _chemical_formula_weight 433.10 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y, z+1/2' 'x+1/2, -y, z+1/2' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1' 'x+1/2, -y+1/2, z+1' _cell_length_a 13.7801(14) _cell_length_b 23.792(2) _cell_length_c 14.665(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4807.9(9) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1848 _exptl_absorpt_coefficient_mu 0.921 _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 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19652 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5807 _reflns_number_gt 5110 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565' _computing_publication_material 'Bruker SMART' _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. The C-1 (C24) and C-2 (C25) atoms of the the pentane molecule whose C-3 (C26) atom lies on a crystallographic C2 axis were disordered and were modeled to give two sets of C24 and C25 positions with a 55/45 occupancy ratio. ; _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^)+(0.0436P)^2^+0.5940P] 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 0.00029(8) _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 -0.005(11) _refine_ls_number_reflns 5807 _refine_ls_number_parameters 301 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0759 _refine_ls_wR_factor_gt 0.0721 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.003 _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 0.838247(13) 0.753231(7) 0.84780(3) 0.03162(7) Uani 1 1 d . . . N2 N 0.76848(10) 0.68411(5) 0.85552(12) 0.0316(3) Uani 1 1 d . . . C2 C 0.65272(13) 0.72037(8) 0.96330(13) 0.0344(4) Uani 1 1 d . . . H2 H 0.5973 0.7104 0.9984 0.041 Uiso 1 1 calc R . . C6 C 0.79063(13) 0.85389(7) 0.94591(13) 0.0329(4) Uani 1 1 d . . . N1 N 0.76133(11) 0.79689(6) 0.93054(10) 0.0320(3) Uani 1 1 d . . . C13 C 0.87060(15) 0.60136(8) 0.83627(17) 0.0476(5) Uani 1 1 d . . . C10 C 0.89204(15) 0.92036(8) 1.02390(15) 0.0421(4) Uani 1 1 d . . . H10 H 0.9381 0.9288 1.0701 0.051 Uiso 1 1 calc R . . C12 C 0.80089(13) 0.63816(7) 0.80104(13) 0.0345(4) Uani 1 1 d . . . C1 C 0.68579(14) 0.77589(8) 0.97380(12) 0.0330(4) Uani 1 1 d . . . C11 C 0.85877(14) 0.86549(8) 1.01487(13) 0.0348(4) Uani 1 1 d . . . C19 C 0.89595(16) 0.81983(8) 1.07604(15) 0.0437(5) Uani 1 1 d . . . H19A H 0.9485 0.8346 1.1142 0.066 Uiso 1 1 calc R . . H19B H 0.9206 0.7887 1.0389 0.066 Uiso 1 1 calc R . . H19C H 0.8431 0.8063 1.1150 0.066 Uiso 1 1 calc R . . C4 C 0.62959(16) 0.81291(9) 1.03937(15) 0.0447(5) Uani 1 1 d . . . H4A H 0.6675 0.8183 1.0952 0.067 Uiso 1 1 calc R . . H4B H 0.5676 0.7949 1.0544 0.067 Uiso 1 1 calc R . . H4C H 0.6173 0.8495 1.0109 0.067 Uiso 1 1 calc R . . C3 C 0.69082(13) 0.67767(7) 0.90778(12) 0.0311(3) Uani 1 1 d . . . C8 C 0.79257(17) 0.95092(8) 0.90085(16) 0.0491(5) Uani 1 1 d . . . H8 H 0.7699 0.9803 0.8626 0.059 Uiso 1 1 calc R . . C5 C 0.63963(15) 0.62156(8) 0.90854(15) 0.0385(4) Uani 1 1 d . . . H5A H 0.6133 0.6138 0.8478 0.058 Uiso 1 1 calc R . . H5B H 0.5866 0.6225 0.9530 0.058 Uiso 1 1 calc R . . H5C H 0.6858 0.5920 0.9253 0.058 Uiso 1 1 calc R . . C9 C 0.85987(18) 0.96266(9) 0.96764(16) 0.0501(5) Uani 1 1 d . . . H9 H 0.8839 0.9998 0.9748 0.060 Uiso 1 1 calc R . . C17 C 0.76968(15) 0.63387(8) 0.71064(13) 0.0416(4) Uani 1 1 d . . . C21 C 0.6963(2) 0.67468(12) 0.67299(17) 0.0607(6) Uani 1 1 d . . . H21A H 0.6968 0.6729 0.6062 0.091 Uiso 1 1 calc R . . H21B H 0.7129 0.7129 0.6927 0.091 Uiso 1 1 calc R . . H21C H 0.6316 0.6649 0.6956 0.091 Uiso 1 1 calc R . . C7 C 0.75711(15) 0.89642(8) 0.88851(14) 0.0407(4) Uani 1 1 d . . . C22 C 0.94450(16) 0.79878(10) 0.79379(17) 0.0474(5) Uani 1 1 d . . . C14 C 0.90459(18) 0.55913(11) 0.7800(2) 0.0672(8) Uani 1 1 d . . . H14 H 0.9508 0.5332 0.8033 0.081 Uiso 1 1 calc R . . C18 C 0.68580(19) 0.88376(10) 0.81396(16) 0.0565(6) Uani 1 1 d . . . H18A H 0.7132 0.8554 0.7729 0.085 Uiso 1 1 calc R . . H18B H 0.6721 0.9182 0.7796 0.085 Uiso 1 1 calc R . . H18C H 0.6255 0.8694 0.8407 0.085 Uiso 1 1 calc R . . C16 C 0.8060(2) 0.59077(11) 0.65727(18) 0.0606(7) Uani 1 1 d . . . H16 H 0.7842 0.5867 0.5962 0.073 Uiso 1 1 calc R . . C15 C 0.8742(2) 0.55336(11) 0.6923(2) 0.0714(9) Uani 1 1 d . . . H15 H 0.8992 0.5240 0.6552 0.086 Uiso 1 1 calc R . . C20 C 0.9061(2) 0.60772(14) 0.9324(2) 0.0737(8) Uani 1 1 d . . . H20A H 0.9615 0.5826 0.9424 0.111 Uiso 1 1 calc R . . H20B H 0.8538 0.5980 0.9748 0.111 Uiso 1 1 calc R . . H20C H 0.9263 0.6467 0.9427 0.111 Uiso 1 1 calc R . . C23 C 0.9512(2) 0.74452(10) 0.76418(19) 0.0493(6) Uani 1 1 d . . . C26 C 1.0000 1.0000 0.7334(4) 0.1122(18) Uani 1 2 d S . . H26A H 0.9506 1.0176 0.7733 0.135 Uiso 0.50 1 calc PR A 1 H26B H 1.0494 0.9824 0.7733 0.135 Uiso 0.50 1 calc PR A 1 C25A C 0.9494(9) 0.9523(3) 0.6754(8) 0.134(3) Uani 0.55 1 d P B 1 H25A H 0.9997 0.9325 0.6395 0.160 Uiso 0.55 1 calc PR B 1 H25B H 0.9201 0.9247 0.7177 0.160 Uiso 0.55 1 calc PR B 1 H22A H 0.9802(16) 0.8115(9) 0.841(2) 0.050(6) Uiso 1 1 d . . . H23A H 0.9944(17) 0.7188(11) 0.7909(18) 0.054(7) Uiso 1 1 d . . . H23B H 0.932(2) 0.7347(12) 0.711(2) 0.060(8) Uiso 1 1 d . . . H22B H 0.9120(18) 0.8272(13) 0.760(2) 0.069(9) Uiso 1 1 d . . . C25B C 0.9107(4) 1.0123(3) 0.6850(5) 0.0655(15) Uani 0.45 1 d P B 2 H25C H 0.9228 1.0444 0.6437 0.079 Uiso 0.45 1 calc PR B 2 H25D H 0.8616 1.0244 0.7301 0.079 Uiso 0.45 1 calc PR B 2 C24A C 0.8811(18) 0.9705(9) 0.619(2) 0.264(15) Uani 0.55 1 d P B 1 H24A H 0.8834 1.0116 0.6154 0.396 Uiso 0.55 1 calc PR B 1 H24B H 0.8173 0.9586 0.6410 0.396 Uiso 0.55 1 calc PR B 1 H24C H 0.8923 0.9546 0.5579 0.396 Uiso 0.55 1 calc PR B 1 C24B C 0.8676(8) 0.9645(7) 0.6289(13) 0.105(5) Uani 0.45 1 d P B 2 H24D H 0.8874 0.9686 0.5651 0.158 Uiso 0.45 1 calc PR B 2 H24E H 0.7966 0.9658 0.6330 0.158 Uiso 0.45 1 calc PR B 2 H24F H 0.8910 0.9284 0.6526 0.158 Uiso 0.45 1 calc PR B 2 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 0.03250(11) 0.02859(10) 0.03377(11) -0.00548(11) 0.00653(11) -0.00110(7) N2 0.0338(7) 0.0275(6) 0.0335(8) -0.0044(7) 0.0026(7) 0.0011(5) C2 0.0343(9) 0.0327(10) 0.0361(10) -0.0024(8) 0.0072(7) -0.0011(7) C6 0.0370(10) 0.0273(8) 0.0343(9) -0.0048(7) 0.0034(8) 0.0034(7) N1 0.0342(8) 0.0274(7) 0.0344(8) -0.0046(6) 0.0035(6) 0.0013(6) C13 0.0448(10) 0.0391(9) 0.0587(14) -0.0001(10) 0.0027(11) 0.0104(8) C10 0.0443(11) 0.0366(10) 0.0454(11) -0.0107(8) -0.0022(9) -0.0009(8) C12 0.0373(9) 0.0263(9) 0.0401(10) -0.0053(7) 0.0074(8) 0.0006(7) C1 0.0348(9) 0.0316(9) 0.0328(9) -0.0035(7) 0.0031(7) 0.0045(7) C11 0.0375(9) 0.0336(9) 0.0333(9) -0.0061(7) 0.0024(7) 0.0049(7) C19 0.0472(12) 0.0430(11) 0.0408(11) -0.0006(9) -0.0021(9) 0.0085(9) C4 0.0443(11) 0.0413(11) 0.0485(12) -0.0112(9) 0.0121(10) 0.0036(8) C3 0.0321(9) 0.0281(8) 0.0332(9) 0.0002(7) -0.0009(7) 0.0013(7) C8 0.0649(14) 0.0304(10) 0.0520(13) 0.0032(9) -0.0022(11) 0.0055(9) C5 0.0413(10) 0.0296(9) 0.0447(11) -0.0003(8) 0.0044(8) -0.0016(7) C9 0.0608(13) 0.0292(10) 0.0601(15) -0.0060(9) -0.0014(11) -0.0033(9) C17 0.0461(11) 0.0402(10) 0.0386(10) -0.0068(8) 0.0055(8) -0.0068(8) C21 0.0661(15) 0.0766(17) 0.0393(12) 0.0019(12) -0.0066(11) 0.0093(13) C7 0.0450(11) 0.0353(10) 0.0418(10) 0.0005(8) -0.0021(8) 0.0045(8) C22 0.0407(11) 0.0534(14) 0.0480(13) -0.0016(10) 0.0101(10) -0.0118(10) C14 0.0610(15) 0.0441(14) 0.097(2) -0.0068(14) 0.0149(14) 0.0204(10) C18 0.0669(14) 0.0510(13) 0.0515(13) 0.0032(10) -0.0180(11) 0.0028(11) C16 0.0678(15) 0.0625(15) 0.0516(13) -0.0255(12) 0.0162(12) -0.0126(13) C15 0.0759(19) 0.0475(14) 0.091(2) -0.0329(14) 0.0333(17) -0.0004(13) C20 0.0637(17) 0.090(2) 0.0677(18) 0.0066(15) -0.0125(13) 0.0338(14) C23 0.0427(13) 0.0535(14) 0.0517(14) -0.0020(11) 0.0188(11) 0.0011(10) C26 0.098(4) 0.135(5) 0.104(4) 0.000 0.000 0.005(4) C25A 0.184(10) 0.070(5) 0.147(8) -0.004(5) 0.020(8) 0.010(6) C25B 0.069(4) 0.064(4) 0.063(4) 0.002(3) -0.006(3) 0.012(3) C24A 0.39(3) 0.170(17) 0.23(2) -0.034(16) -0.03(2) 0.182(19) C24B 0.060(5) 0.109(10) 0.147(11) -0.078(9) -0.047(6) 0.027(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 N2 1.9082(13) . ? Cu1 N1 1.9168(15) . ? Cu1 C22 1.986(2) . ? Cu1 C23 1.992(2) . ? N2 C3 1.325(2) . ? N2 C12 1.426(2) . ? C2 C3 1.404(2) . ? C2 C1 1.406(3) . ? C6 C7 1.395(3) . ? C6 C11 1.407(3) . ? C6 N1 1.433(2) . ? N1 C1 1.317(2) . ? C13 C14 1.382(3) . ? C13 C12 1.399(3) . ? C13 C20 1.500(4) . ? C10 C9 1.375(3) . ? C10 C11 1.390(3) . ? C12 C17 1.397(3) . ? C1 C4 1.517(3) . ? C11 C19 1.499(3) . ? C3 C5 1.510(3) . ? C8 C9 1.378(3) . ? C8 C7 1.397(3) . ? C17 C16 1.384(3) . ? C17 C21 1.506(3) . ? C7 C18 1.501(3) . ? C22 C23 1.365(3) . ? C14 C15 1.359(5) . ? C16 C15 1.392(5) . ? C26 C25B 1.450(7) 2_775 ? C26 C25B 1.450(7) . ? C26 C25A 1.580(11) 2_775 ? C26 C25A 1.580(11) . ? C25A C24A 1.33(2) . ? C25B C24B 1.524(12) . ? 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 N2 Cu1 N1 98.68(6) . . ? N2 Cu1 C22 149.90(8) . . ? N1 Cu1 C22 111.37(8) . . ? N2 Cu1 C23 109.90(8) . . ? N1 Cu1 C23 151.39(8) . . ? C22 Cu1 C23 40.13(9) . . ? C3 N2 C12 119.23(14) . . ? C3 N2 Cu1 122.74(11) . . ? C12 N2 Cu1 118.02(12) . . ? C3 C2 C1 128.48(17) . . ? C7 C6 C11 120.82(17) . . ? C7 C6 N1 119.90(17) . . ? C11 C6 N1 119.12(16) . . ? C1 N1 C6 120.38(15) . . ? C1 N1 Cu1 122.43(12) . . ? C6 N1 Cu1 117.17(12) . . ? C14 C13 C12 117.8(2) . . ? C14 C13 C20 121.6(2) . . ? C12 C13 C20 120.54(19) . . ? C9 C10 C11 121.6(2) . . ? C17 C12 C13 121.07(18) . . ? C17 C12 N2 119.41(17) . . ? C13 C12 N2 119.22(18) . . ? N1 C1 C2 124.04(16) . . ? N1 C1 C4 119.25(17) . . ? C2 C1 C4 116.71(16) . . ? C10 C11 C6 118.21(18) . . ? C10 C11 C19 120.72(18) . . ? C6 C11 C19 121.06(17) . . ? N2 C3 C2 123.63(16) . . ? N2 C3 C5 118.94(15) . . ? C2 C3 C5 117.44(16) . . ? C9 C8 C7 121.0(2) . . ? C10 C9 C8 119.70(19) . . ? C16 C17 C12 118.6(2) . . ? C16 C17 C21 120.9(2) . . ? C12 C17 C21 120.48(18) . . ? C6 C7 C8 118.64(19) . . ? C6 C7 C18 120.72(18) . . ? C8 C7 C18 120.64(19) . . ? C23 C22 Cu1 70.17(13) . . ? C15 C14 C13 122.3(3) . . ? C17 C16 C15 120.6(2) . . ? C14 C15 C16 119.5(2) . . ? C22 C23 Cu1 69.70(13) . . ? C25B C26 C25B 121.4(7) 2_775 . ? C25B C26 C25A 60.4(5) 2_775 2_775 ? C25B C26 C25A 88.1(5) . 2_775 ? C25B C26 C25A 88.1(5) 2_775 . ? C25B C26 C25A 60.4(5) . . ? C25A C26 C25A 114.8(9) 2_775 . ? C24A C25A C26 114.6(11) . . ? C26 C25B C24B 116.4(7) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.268 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.043 #======================================================================== data_dai162 _database_code_CSD 168945 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Me2NN]Cu(styrene)' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H33 Cu N2' _chemical_formula_weight 473.11 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 17.4077(14) _cell_length_b 15.3217(12) _cell_length_c 18.5088(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4936.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 0.903 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; As evidenced by the large number of reflections 'not observed' rejected by the criterion F^2^ > 2sigma(F^2^) (2351 / 4355 - see below), many of the higher angle reflections were weak for this crystal. Refinement as described below, however, gives a solution with normal metrical parameters (e.g. C-C distances in phenyl rings) and esds. ; _diffrn_ambient_temperature 173(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 43388 _diffrn_reflns_av_R_equivalents 0.1818 _diffrn_reflns_av_sigmaI/netI 0.1033 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4355 _reflns_number_gt 2351 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0627P)^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 0.0022(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4355 _refine_ls_number_parameters 308 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1204 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1240 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 0.868 _refine_ls_restrained_S_all 0.868 _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 0.19148(3) 0.05321(3) -0.16682(3) 0.02695(18) Uani 1 1 d . . . N1 N 0.19752(19) 0.0214(2) -0.06705(17) 0.0251(8) Uani 1 1 d . . . N2 N 0.09652(18) 0.1162(2) -0.16471(18) 0.0261(8) Uani 1 1 d . . . C23 C 0.2390(3) 0.0502(3) -0.2668(2) 0.0289(10) Uani 1 1 d . . . C14 C -0.0073(2) 0.0982(3) -0.3392(2) 0.0339(11) Uani 1 1 d . . . H14 H -0.0334 0.0563 -0.3660 0.041 Uiso 1 1 calc R . . C27 C 0.3114(3) 0.3046(3) -0.3317(3) 0.0406(12) Uani 1 1 d . . . H27 H 0.3266 0.3601 -0.3460 0.049 Uiso 1 1 calc R . . C12 C 0.0622(2) 0.1404(3) -0.2320(2) 0.0240(10) Uani 1 1 d . . . C16 C 0.0400(2) 0.2433(3) -0.3271(2) 0.0318(11) Uani 1 1 d . . . H16 H 0.0452 0.2993 -0.3458 0.038 Uiso 1 1 calc R . . C3 C 0.0580(2) 0.1297(3) -0.1035(2) 0.0284(10) Uani 1 1 d . . . C22 C 0.2759(4) -0.0048(4) -0.2195(3) 0.0373(13) Uani 1 1 d . . . C24 C 0.2651(2) 0.1379(3) -0.2883(2) 0.0285(11) Uani 1 1 d . . . C6 C 0.2566(2) -0.0398(3) -0.0467(2) 0.0253(10) Uani 1 1 d . . . C1 C 0.1461(2) 0.0482(3) -0.0184(2) 0.0281(10) Uani 1 1 d . . . C17 C 0.0723(2) 0.2240(3) -0.2602(2) 0.0258(10) Uani 1 1 d . . . C10 C 0.3025(3) -0.1873(3) -0.0423(2) 0.0357(12) Uani 1 1 d . . . H10 H 0.2941 -0.2468 -0.0483 0.043 Uiso 1 1 calc R . . C8 C 0.3858(3) -0.0701(3) -0.0115(2) 0.0362(12) Uani 1 1 d . . . H8 H 0.4337 -0.0510 0.0042 0.043 Uiso 1 1 calc R . . C25 C 0.2321(3) 0.1785(3) -0.3485(2) 0.0321(11) Uani 1 1 d . . . H25 H 0.1940 0.1497 -0.3745 0.038 Uiso 1 1 calc R . . C26 C 0.2553(3) 0.2606(3) -0.3696(2) 0.0396(12) Uani 1 1 d . . . H26 H 0.2329 0.2866 -0.4098 0.047 Uiso 1 1 calc R . . C28 C 0.3447(3) 0.2657(3) -0.2725(3) 0.0392(12) Uani 1 1 d . . . H28 H 0.3829 0.2948 -0.2470 0.047 Uiso 1 1 calc R . . C13 C 0.0236(2) 0.0763(3) -0.2721(2) 0.0313(11) Uani 1 1 d . . . C21 C 0.1190(3) 0.2908(3) -0.2201(2) 0.0328(11) Uani 1 1 d . . . H21A H 0.1273 0.3406 -0.2506 0.049 Uiso 1 1 calc R . . H21B H 0.1675 0.2660 -0.2068 0.049 Uiso 1 1 calc R . . H21C H 0.0918 0.3085 -0.1774 0.049 Uiso 1 1 calc R . . C2 C 0.0833(2) 0.1002(3) -0.0356(2) 0.0297(11) Uani 1 1 d . . . H2 H 0.0537 0.1182 0.0035 0.036 Uiso 1 1 calc R . . C15 C 0.0008(2) 0.1819(3) -0.3660(2) 0.0337(11) Uani 1 1 d . . . H15 H -0.0205 0.1964 -0.4105 0.040 Uiso 1 1 calc R . . C29 C 0.3213(2) 0.1832(3) -0.2506(2) 0.0322(11) Uani 1 1 d . . . H29 H 0.3437 0.1579 -0.2101 0.039 Uiso 1 1 calc R . . C7 C 0.3282(2) -0.0088(3) -0.0253(2) 0.0276(10) Uani 1 1 d . . . C4 C 0.1542(3) 0.0182(3) 0.0598(2) 0.0368(12) Uani 1 1 d . . . H4A H 0.1531 -0.0444 0.0617 0.055 Uiso 1 1 calc R . . H4B H 0.1126 0.0413 0.0880 0.055 Uiso 1 1 calc R . . H4C H 0.2022 0.0388 0.0790 0.055 Uiso 1 1 calc R . . C11 C 0.2429(3) -0.1295(3) -0.0555(2) 0.0275(10) Uani 1 1 d . . . C5 C -0.0181(2) 0.1765(3) -0.1062(2) 0.0400(12) Uani 1 1 d . . . H5A H -0.0103 0.2355 -0.1222 0.060 Uiso 1 1 calc R . . H5B H -0.0407 0.1770 -0.0589 0.060 Uiso 1 1 calc R . . H5C H -0.0518 0.1470 -0.1392 0.060 Uiso 1 1 calc R . . C9 C 0.3731(3) -0.1588(3) -0.0206(2) 0.0388(12) Uani 1 1 d . . . H9 H 0.4124 -0.1985 -0.0121 0.047 Uiso 1 1 calc R . . C20 C 0.0135(3) -0.0147(3) -0.2421(3) 0.0460(13) Uani 1 1 d . . . H20A H -0.0097 -0.0513 -0.2781 0.069 Uiso 1 1 calc R . . H20B H -0.0190 -0.0126 -0.2002 0.069 Uiso 1 1 calc R . . H20C H 0.0627 -0.0381 -0.2289 0.069 Uiso 1 1 calc R . . C19 C 0.1646(3) -0.1614(3) -0.0790(3) 0.0429(13) Uani 1 1 d . . . H19A H 0.1672 -0.2226 -0.0899 0.064 Uiso 1 1 calc R . . H19B H 0.1487 -0.1300 -0.1213 0.064 Uiso 1 1 calc R . . H19C H 0.1282 -0.1519 -0.0408 0.064 Uiso 1 1 calc R . . C18 C 0.3432(3) 0.0878(3) -0.0181(3) 0.0396(12) Uani 1 1 d . . . H18A H 0.3385 0.1151 -0.0646 0.059 Uiso 1 1 calc R . . H18B H 0.3942 0.0969 0.0002 0.059 Uiso 1 1 calc R . . H18C H 0.3065 0.1128 0.0146 0.059 Uiso 1 1 calc R . . H23 H 0.206(2) 0.024(3) -0.298(2) 0.028(12) Uiso 1 1 d . . . H22A H 0.263(3) -0.060(3) -0.218(2) 0.044(15) Uiso 1 1 d . . . H22B H 0.321(2) 0.012(3) -0.202(2) 0.023(13) 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 0.0298(3) 0.0253(3) 0.0257(3) 0.0033(3) 0.0031(3) 0.0046(3) N1 0.029(2) 0.0192(17) 0.027(2) 0.0014(15) 0.0032(17) 0.0012(16) N2 0.030(2) 0.0239(19) 0.024(2) 0.0014(17) 0.0020(17) -0.0003(15) C23 0.033(3) 0.030(2) 0.024(2) -0.001(2) 0.006(2) 0.002(2) C14 0.021(2) 0.045(3) 0.036(3) -0.010(2) -0.002(2) -0.004(2) C27 0.049(3) 0.030(2) 0.043(3) -0.002(2) 0.012(3) -0.002(2) C12 0.020(2) 0.028(2) 0.024(2) -0.0037(19) 0.006(2) 0.0006(19) C16 0.026(3) 0.032(3) 0.037(3) 0.011(2) 0.001(2) 0.004(2) C3 0.035(3) 0.019(2) 0.031(3) -0.002(2) 0.003(2) -0.005(2) C22 0.044(4) 0.031(3) 0.037(3) 0.005(3) 0.004(3) 0.008(3) C24 0.028(3) 0.034(3) 0.024(3) -0.003(2) 0.006(2) 0.008(2) C6 0.032(3) 0.025(3) 0.019(2) 0.0074(19) 0.0014(19) 0.007(2) C1 0.032(3) 0.022(2) 0.031(2) 0.000(2) 0.002(2) -0.006(2) C17 0.023(3) 0.024(2) 0.030(3) 0.003(2) 0.003(2) 0.0043(19) C10 0.061(4) 0.022(2) 0.024(2) 0.0036(19) 0.003(2) 0.004(3) C8 0.031(3) 0.048(3) 0.030(3) 0.002(2) -0.005(2) 0.001(2) C25 0.033(3) 0.032(3) 0.030(3) 0.001(2) 0.001(2) 0.003(2) C26 0.050(3) 0.037(3) 0.032(3) 0.005(2) -0.003(2) 0.005(3) C28 0.032(3) 0.049(3) 0.037(3) -0.010(3) 0.007(2) -0.004(2) C13 0.024(3) 0.031(3) 0.039(3) -0.003(2) 0.005(2) -0.002(2) C21 0.033(3) 0.025(2) 0.040(3) 0.009(2) -0.006(2) 0.005(2) C2 0.031(3) 0.030(3) 0.027(3) 0.002(2) 0.009(2) 0.002(2) C15 0.025(3) 0.051(3) 0.026(2) 0.004(2) 0.001(2) 0.005(2) C29 0.031(3) 0.039(3) 0.026(2) -0.001(2) 0.001(2) 0.007(2) C7 0.034(3) 0.026(2) 0.023(2) 0.005(2) 0.006(2) -0.001(2) C4 0.049(3) 0.039(3) 0.022(3) 0.006(2) 0.006(2) 0.004(2) C11 0.038(3) 0.022(2) 0.022(2) 0.003(2) 0.000(2) -0.002(2) C5 0.031(3) 0.047(3) 0.042(3) 0.003(2) 0.007(2) 0.009(2) C9 0.048(3) 0.039(3) 0.029(3) 0.012(2) -0.001(2) 0.012(3) C20 0.045(3) 0.031(3) 0.062(4) -0.006(3) 0.000(3) -0.013(2) C19 0.052(3) 0.030(3) 0.047(3) 0.002(2) -0.003(3) -0.013(2) C18 0.045(3) 0.032(3) 0.042(3) 0.000(2) 0.006(2) -0.006(2) _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 1.913(3) . ? Cu1 N2 1.915(3) . ? Cu1 C22 1.975(5) . ? Cu1 C23 2.027(4) . ? N1 C1 1.334(5) . ? N1 C6 1.441(5) . ? N2 C3 1.332(5) . ? N2 C12 1.431(5) . ? C23 C22 1.373(6) . ? C23 C24 1.474(6) . ? C14 C15 1.383(6) . ? C14 C13 1.395(6) . ? C27 C28 1.375(6) . ? C27 C26 1.379(6) . ? C12 C17 1.394(5) . ? C12 C13 1.402(6) . ? C16 C15 1.368(6) . ? C16 C17 1.392(5) . ? C3 C2 1.407(6) . ? C3 C5 1.508(6) . ? C24 C29 1.388(6) . ? C24 C25 1.399(6) . ? C6 C7 1.393(6) . ? C6 C11 1.404(5) . ? C1 C2 1.390(6) . ? C1 C4 1.526(5) . ? C17 C21 1.503(6) . ? C10 C9 1.365(6) . ? C10 C11 1.385(6) . ? C8 C9 1.388(6) . ? C8 C7 1.397(6) . ? C25 C26 1.378(6) . ? C28 C29 1.387(6) . ? C13 C20 1.511(6) . ? C7 C18 1.508(6) . ? C11 C19 1.512(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N2 98.99(14) . . ? N1 Cu1 C22 108.74(18) . . ? N2 Cu1 C22 151.55(19) . . ? N1 Cu1 C23 148.52(17) . . ? N2 Cu1 C23 112.49(16) . . ? C22 Cu1 C23 40.11(18) . . ? C1 N1 C6 120.2(3) . . ? C1 N1 Cu1 122.4(3) . . ? C6 N1 Cu1 117.2(2) . . ? C3 N2 C12 119.3(3) . . ? C3 N2 Cu1 122.0(3) . . ? C12 N2 Cu1 118.3(3) . . ? C22 C23 C24 126.0(5) . . ? C22 C23 Cu1 67.9(3) . . ? C24 C23 Cu1 110.6(3) . . ? C15 C14 C13 120.2(4) . . ? C28 C27 C26 119.5(4) . . ? C17 C12 C13 120.4(4) . . ? C17 C12 N2 120.7(4) . . ? C13 C12 N2 118.6(4) . . ? C15 C16 C17 121.6(4) . . ? N2 C3 C2 123.5(4) . . ? N2 C3 C5 119.2(4) . . ? C2 C3 C5 117.2(4) . . ? C23 C22 Cu1 72.0(3) . . ? C29 C24 C25 117.9(4) . . ? C29 C24 C23 122.5(4) . . ? C25 C24 C23 119.6(4) . . ? C7 C6 C11 121.2(4) . . ? C7 C6 N1 119.4(4) . . ? C11 C6 N1 119.0(4) . . ? N1 C1 C2 123.4(4) . . ? N1 C1 C4 119.0(4) . . ? C2 C1 C4 117.6(4) . . ? C16 C17 C12 118.5(4) . . ? C16 C17 C21 120.9(4) . . ? C12 C17 C21 120.6(4) . . ? C9 C10 C11 121.4(4) . . ? C9 C8 C7 121.5(4) . . ? C26 C25 C24 120.7(4) . . ? C25 C26 C27 120.7(4) . . ? C27 C28 C29 120.2(4) . . ? C14 C13 C12 119.1(4) . . ? C14 C13 C20 120.2(4) . . ? C12 C13 C20 120.6(4) . . ? C1 C2 C3 129.4(4) . . ? C16 C15 C14 120.0(4) . . ? C24 C29 C28 121.1(4) . . ? C6 C7 C8 117.7(4) . . ? C6 C7 C18 121.0(4) . . ? C8 C7 C18 121.3(4) . . ? C10 C11 C6 118.6(4) . . ? C10 C11 C19 121.2(4) . . ? C6 C11 C19 120.2(4) . . ? C10 C9 C8 119.5(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.415 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.087 #======================================================================== data_144b _database_code_CSD 168946 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '{[Me2NN]Cu(OH)}2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H52 Cu2 N4 O2' _chemical_formula_weight 771.96 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.5194(15) _cell_length_b 10.6093(7) _cell_length_c 15.2554(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.1880(10) _cell_angle_gamma 90.00 _cell_volume 3800.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1624 _exptl_absorpt_coefficient_mu 1.160 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.67 _exptl_absorpt_correction_T_max 0.54 _exptl_absorpt_process_details 'SADABS based on Blessing's method; Blessing, Acta Cryst. (1995) A51 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20485 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0131 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4581 _reflns_number_gt 4253 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows; Ferrugia L J (1997), J. Appl. Cryst. 30, 565' _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^)+(0.0359P)^2^+3.6076P] 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 4581 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0274 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0701 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.225403(6) 0.684430(15) 0.078720(10) 0.01952(6) Uani 1 1 d . . . N2 N 0.14806(5) 0.66272(11) 0.11362(7) 0.0213(2) Uani 1 1 d . . . O1 O 0.29556(5) 0.73355(13) 0.03075(8) 0.0371(3) Uani 1 1 d . . . N1 N 0.26006(5) 0.59422(11) 0.17899(7) 0.0224(2) Uani 1 1 d . . . C12 C 0.10195(6) 0.67647(13) 0.04835(9) 0.0233(3) Uani 1 1 d . . . C11 C 0.32909(6) 0.43975(14) 0.13185(10) 0.0300(3) Uani 1 1 d . . . C6 C 0.31803(6) 0.55248(13) 0.17533(9) 0.0235(3) Uani 1 1 d . . . C1 C 0.23275(6) 0.56519(13) 0.25009(9) 0.0250(3) Uani 1 1 d . . . C17 C 0.07411(6) 0.79205(15) 0.03659(10) 0.0291(3) Uani 1 1 d . . . C20 C 0.11796(8) 0.44919(16) 0.00834(12) 0.0391(4) Uani 1 1 d . . . H20A H 0.0982 0.3837 -0.0269 0.059 Uiso 1 1 calc R . . H20B H 0.1195 0.4249 0.0704 0.059 Uiso 1 1 calc R . . H20C H 0.1568 0.4590 -0.0109 0.059 Uiso 1 1 calc R . . C8 C 0.41810(6) 0.58051(17) 0.20902(11) 0.0349(3) Uani 1 1 d . . . H8 H 0.4487 0.6284 0.2350 0.042 Uiso 1 1 calc R . . C2 C 0.17490(6) 0.59043(14) 0.25929(9) 0.0268(3) Uani 1 1 d . . . H2 H 0.1615 0.5807 0.3165 0.032 Uiso 1 1 calc R . . C13 C 0.08654(6) 0.57180(15) -0.00331(9) 0.0288(3) Uani 1 1 d . . . C5 C 0.07304(6) 0.62216(17) 0.21645(10) 0.0328(3) Uani 1 1 d . . . H5A H 0.0543 0.7024 0.2014 0.049 Uiso 1 1 calc R . . H5B H 0.0709 0.6063 0.2795 0.049 Uiso 1 1 calc R . . H5C H 0.0539 0.5538 0.1832 0.049 Uiso 1 1 calc R . . C16 C 0.02843(7) 0.79880(18) -0.02580(12) 0.0385(4) Uani 1 1 d . . . H16 H 0.0081 0.8757 -0.0334 0.046 Uiso 1 1 calc R . . C14 C 0.04143(7) 0.58399(19) -0.06589(10) 0.0390(4) Uani 1 1 d . . . H14 H 0.0305 0.5139 -0.1018 0.047 Uiso 1 1 calc R . . C3 C 0.13491(6) 0.62825(13) 0.19371(9) 0.0234(3) Uani 1 1 d . . . C9 C 0.42941(7) 0.46829(18) 0.16833(12) 0.0391(4) Uani 1 1 d . . . H9 H 0.4675 0.4386 0.1669 0.047 Uiso 1 1 calc R . . C7 C 0.36269(6) 0.62541(15) 0.21286(10) 0.0282(3) Uani 1 1 d . . . C15 C 0.01241(7) 0.6961(2) -0.07641(12) 0.0436(4) Uani 1 1 d . . . H15 H -0.0187 0.7026 -0.1186 0.052 Uiso 1 1 calc R . . C10 C 0.38535(7) 0.39926(17) 0.12967(11) 0.0380(4) Uani 1 1 d . . . H10 H 0.3934 0.3224 0.1009 0.046 Uiso 1 1 calc R . . C4 C 0.26376(7) 0.49720(17) 0.32554(10) 0.0354(3) Uani 1 1 d . . . H4A H 0.2806 0.4194 0.3040 0.053 Uiso 1 1 calc R . . H4B H 0.2369 0.4766 0.3702 0.053 Uiso 1 1 calc R . . H4C H 0.2939 0.5516 0.3514 0.053 Uiso 1 1 calc R . . C18 C 0.35171(7) 0.74976(17) 0.25610(13) 0.0419(4) Uani 1 1 d . . . H18A H 0.3382 0.7350 0.3148 0.063 Uiso 1 1 calc R . . H18B H 0.3228 0.7965 0.2207 0.063 Uiso 1 1 calc R . . H18C H 0.3871 0.7988 0.2610 0.063 Uiso 1 1 calc R . . C19 C 0.28144(8) 0.36362(17) 0.08865(13) 0.0431(4) Uani 1 1 d . . . H19A H 0.2967 0.2851 0.0658 0.065 Uiso 1 1 calc R . . H19B H 0.2631 0.4122 0.0403 0.065 Uiso 1 1 calc R . . H19C H 0.2534 0.3440 0.1318 0.065 Uiso 1 1 calc R . . C21 C 0.09319(7) 0.90614(16) 0.08784(12) 0.0395(4) Uani 1 1 d . . . H21A H 0.0950 0.8863 0.1507 0.059 Uiso 1 1 calc R . . H21B H 0.0661 0.9750 0.0760 0.059 Uiso 1 1 calc R . . H21C H 0.1310 0.9318 0.0705 0.059 Uiso 1 1 calc R . . H22 H 0.3246(11) 0.719(2) 0.0480(16) 0.057(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01430(9) 0.02414(10) 0.02007(9) 0.00334(6) 0.00040(6) 0.00055(5) N2 0.0151(5) 0.0274(6) 0.0213(5) 0.0009(4) -0.0003(4) -0.0001(4) O1 0.0154(5) 0.0617(8) 0.0341(6) 0.0236(6) 0.0004(4) 0.0020(5) N1 0.0176(5) 0.0259(6) 0.0235(5) 0.0028(4) -0.0006(4) 0.0013(4) C12 0.0152(6) 0.0341(7) 0.0206(6) 0.0026(5) 0.0012(5) -0.0026(5) C11 0.0293(7) 0.0282(7) 0.0322(7) 0.0030(6) -0.0004(6) 0.0038(6) C6 0.0193(6) 0.0269(7) 0.0243(6) 0.0057(5) -0.0001(5) 0.0025(5) C1 0.0237(6) 0.0285(7) 0.0225(6) 0.0033(5) -0.0019(5) -0.0007(5) C17 0.0184(6) 0.0382(8) 0.0307(7) 0.0045(6) 0.0009(5) 0.0014(5) C20 0.0407(9) 0.0354(8) 0.0413(9) -0.0096(7) 0.0023(7) -0.0036(7) C8 0.0202(7) 0.0440(9) 0.0402(8) 0.0093(7) -0.0016(6) -0.0006(6) C2 0.0239(7) 0.0360(8) 0.0204(6) 0.0031(5) 0.0018(5) -0.0011(6) C13 0.0239(6) 0.0385(8) 0.0241(6) -0.0007(6) 0.0028(5) -0.0072(6) C5 0.0202(7) 0.0514(10) 0.0270(7) 0.0045(6) 0.0041(5) -0.0022(6) C16 0.0216(7) 0.0519(10) 0.0413(9) 0.0145(7) -0.0035(6) 0.0027(6) C14 0.0316(8) 0.0577(11) 0.0271(7) -0.0029(7) -0.0034(6) -0.0155(7) C3 0.0188(6) 0.0278(7) 0.0236(6) -0.0005(5) 0.0026(5) -0.0012(5) C9 0.0229(7) 0.0495(10) 0.0453(9) 0.0117(8) 0.0062(6) 0.0112(7) C7 0.0222(6) 0.0322(7) 0.0297(7) 0.0042(6) -0.0021(5) 0.0003(5) C15 0.0257(8) 0.0706(13) 0.0331(8) 0.0123(8) -0.0094(6) -0.0101(8) C10 0.0369(8) 0.0359(8) 0.0414(9) 0.0023(7) 0.0052(7) 0.0136(7) C4 0.0278(7) 0.0493(9) 0.0288(7) 0.0144(7) -0.0017(6) 0.0019(7) C18 0.0320(8) 0.0388(9) 0.0539(10) -0.0116(8) -0.0073(7) -0.0024(7) C19 0.0420(9) 0.0338(8) 0.0523(10) -0.0100(8) -0.0064(8) 0.0012(7) C21 0.0325(8) 0.0349(8) 0.0507(10) -0.0017(7) -0.0029(7) 0.0080(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 O1 1.9142(11) . ? Cu1 O1 1.9230(11) 7_565 ? Cu1 N2 1.9373(11) . ? Cu1 N1 1.9446(11) . ? Cu1 Cu1 3.0581(3) 7_565 ? N2 C3 1.3283(17) . ? N2 C12 1.4384(17) . ? O1 Cu1 1.9230(11) 7_565 ? N1 C1 1.3271(18) . ? N1 C6 1.4377(16) . ? C12 C17 1.397(2) . ? C12 C13 1.398(2) . ? C11 C10 1.393(2) . ? C11 C6 1.399(2) . ? C11 C19 1.504(2) . ? C6 C7 1.401(2) . ? C1 C2 1.4014(19) . ? C1 C4 1.5112(19) . ? C17 C16 1.397(2) . ? C17 C21 1.496(2) . ? C20 C13 1.502(2) . ? C8 C9 1.376(3) . ? C8 C7 1.392(2) . ? C2 C3 1.3935(19) . ? C13 C14 1.393(2) . ? C5 C3 1.5159(18) . ? C16 C15 1.376(3) . ? C14 C15 1.376(3) . ? C9 C10 1.375(3) . ? C7 C18 1.504(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 O1 Cu1 O1 74.32(5) . 7_565 ? O1 Cu1 N2 168.51(5) . . ? O1 Cu1 N2 95.34(5) 7_565 . ? O1 Cu1 N1 95.86(5) . . ? O1 Cu1 N1 169.08(5) 7_565 . ? N2 Cu1 N1 94.83(5) . . ? O1 Cu1 Cu1 37.26(3) . 7_565 ? O1 Cu1 Cu1 37.06(3) 7_565 7_565 ? N2 Cu1 Cu1 132.22(3) . 7_565 ? N1 Cu1 Cu1 132.95(3) . 7_565 ? C3 N2 C12 117.35(11) . . ? C3 N2 Cu1 123.76(9) . . ? C12 N2 Cu1 118.76(9) . . ? Cu1 O1 Cu1 105.68(5) . 7_565 ? C1 N1 C6 117.61(11) . . ? C1 N1 Cu1 123.81(9) . . ? C6 N1 Cu1 118.55(9) . . ? C17 C12 C13 121.34(13) . . ? C17 C12 N2 120.52(13) . . ? C13 C12 N2 118.14(13) . . ? C10 C11 C6 118.48(14) . . ? C10 C11 C19 120.65(15) . . ? C6 C11 C19 120.88(14) . . ? C11 C6 C7 120.72(13) . . ? C11 C6 N1 118.92(12) . . ? C7 C6 N1 120.34(13) . . ? N1 C1 C2 123.65(12) . . ? N1 C1 C4 119.89(13) . . ? C2 C1 C4 116.42(12) . . ? C12 C17 C16 118.01(15) . . ? C12 C17 C21 121.22(13) . . ? C16 C17 C21 120.76(15) . . ? C9 C8 C7 121.35(15) . . ? C3 C2 C1 127.12(13) . . ? C14 C13 C12 118.44(15) . . ? C14 C13 C20 120.83(15) . . ? C12 C13 C20 120.73(13) . . ? C15 C16 C17 121.19(16) . . ? C15 C14 C13 120.93(16) . . ? N2 C3 C2 123.87(12) . . ? N2 C3 C5 119.86(12) . . ? C2 C3 C5 116.20(12) . . ? C10 C9 C8 119.64(14) . . ? C8 C7 C6 118.44(15) . . ? C8 C7 C18 120.17(14) . . ? C6 C7 C18 121.38(13) . . ? C16 C15 C14 120.03(15) . . ? C9 C10 C11 121.31(16) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.316 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.052