Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global # *** Added by check_cif _journal_coden_Cambridge 182 loop_ _publ_author_name 'Polly L. Arnold' 'Andrew C. Scarisbrick' 'Alexander J. Blake' 'Claire Wilson' _publ_contact_author_name 'Dr Polly Arnold' _publ_contact_author_address ; School of Chemistry The University of Nottingham University Park Nottingham NG7 2RD England UK ; _publ_contact_author_email Polly.Arnold@nottingham.ac.uk _publ_contact_author_fax '0115 951 3563' _publ_contact_author_phone '0115 951 3437' _publ_requested_journal 'Chem. Comm.' _publ_section_title ; Chelating Alkoxy-N-Heterocyclic Carbene Complexes of Silver and Copper ; #=========================================================================== #== data_phimcl _database_code_CSD 169965 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H40 Cl2 N4 O4' _chemical_formula_weight 507.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 20.5270(6) _cell_length_b 11.3091(4) _cell_length_c 13.0364(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.933(2) _cell_angle_gamma 90.00 _cell_volume 2826.55(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.262 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9373 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD area detector' _diffrn_measurement_method 'phi & omega' diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10342 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4294 _reflns_number_gt 3201 _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^)+(0.1495P)^2^+1.2507P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geometrically placed, H2O not located' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.43(11) _refine_ls_number_reflns 4290 _refine_ls_number_parameters 299 _refine_ls_number_restraints 117 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0747 _refine_ls_wR_factor_ref 0.2163 _refine_ls_wR_factor_gt 0.1935 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.005 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 Cl2 Cl 0.29813(11) 0.51497(15) 0.25149(15) 0.0562(5) Uani 1 1 d . . . Cl1 Cl 0.56614(9) 0.53032(15) -0.19522(14) 0.0493(4) Uani 1 1 d . . . O1 O 0.4409(2) 0.8081(4) 0.1262(4) 0.0510(12) Uani 1 1 d DU . . H1 H 0.4461 0.7632 0.1799 0.077 Uiso 1 1 calc RD . . N3 N 0.3042(3) 0.7322(4) 0.0020(4) 0.0367(11) Uani 1 1 d U . . N4 N 0.2331(3) 0.8363(4) 0.0548(4) 0.0377(12) Uani 1 1 d U . . N1 N 0.5539(2) 0.7269(4) 0.0548(4) 0.0379(12) Uani 1 1 d U . . N2 N 0.6236(3) 0.8372(4) 0.0068(4) 0.0375(12) Uani 1 1 d U . . C11 C 0.4193(2) 0.8227(4) -0.0651(4) 0.0297(12) Uani 1 1 d DU . . C12 C 0.4339(2) 0.9412(5) -0.0432(4) 0.0565(16) Uani 1 1 d DU . . H12A H 0.4466 0.9714 0.0293 0.068 Uiso 1 1 calc R . . C13 C 0.4295(3) 1.0145(5) -0.1302(6) 0.073(2) Uani 1 1 d DU . . H13A H 0.4393 1.0964 -0.1171 0.088 Uiso 1 1 calc R . . C14 C 0.4113(4) 0.9718(5) -0.2345(6) 0.079(3) Uani 1 1 d DU . . H14A H 0.4085 1.0234 -0.2935 0.094 Uiso 1 1 calc R . . C15 C 0.3972(3) 0.8542(6) -0.2535(5) 0.0604(18) Uani 1 1 d DU . . H15A H 0.3844 0.8244 -0.3261 0.072 Uiso 1 1 calc R . . C16 C 0.4011(3) 0.7782(5) -0.1690(5) 0.0534(15) Uani 1 1 d DU . . H16A H 0.3913 0.6963 -0.1827 0.064 Uiso 1 1 calc R . . C10 C 0.4279(4) 0.7386(4) 0.0291(6) 0.0354(10) Uani 1 1 d U . . C21 C 0.3634(3) 0.6590(5) 0.0094(6) 0.0402(14) Uani 1 1 d U . . H21A H 0.3535 0.6136 -0.0595 0.048 Uiso 1 1 calc R . . H21B H 0.3726 0.6021 0.0707 0.048 Uiso 1 1 calc R . . C22 C 0.2866(3) 0.7620(5) 0.0878(5) 0.0362(14) Uani 1 1 d U . . H22A H 0.3088 0.7344 0.1609 0.043 Uiso 1 1 calc R . . C23 C 0.2600(3) 0.7904(6) -0.0896(5) 0.0421(14) Uani 1 1 d U . . H23A H 0.2611 0.7873 -0.1618 0.051 Uiso 1 1 calc R . . C24 C 0.2155(3) 0.8521(6) -0.0567(5) 0.0438(15) Uani 1 1 d U . . H24A H 0.1780 0.8991 -0.1024 0.053 Uiso 1 1 calc R . . C25 C 0.1952(3) 0.8886(5) 0.1251(4) 0.0463(16) Uani 1 1 d DU . . C28 C 0.2350(3) 0.8570(6) 0.2445(4) 0.0513(17) Uani 1 1 d DU . . H28A H 0.2354 0.7710 0.2534 0.077 Uiso 1 1 calc R . . H28B H 0.2122 0.8937 0.2910 0.077 Uiso 1 1 calc R . . H28C H 0.2830 0.8861 0.2662 0.077 Uiso 1 1 calc R . . C27 C 0.1943(4) 1.0226(5) 0.1090(6) 0.063(2) Uani 1 1 d DU . . H27A H 0.1687 1.0416 0.0317 0.095 Uiso 1 1 calc R . . H27B H 0.2423 1.0518 0.1302 0.095 Uiso 1 1 calc R . . H27C H 0.1715 1.0604 0.1548 0.095 Uiso 1 1 calc R . . C26 C 0.1228(3) 0.8361(6) 0.0837(5) 0.0554(18) Uani 1 1 d DU . . H26A H 0.1259 0.7502 0.0943 0.083 Uiso 1 1 calc R . . H26B H 0.1000 0.8539 0.0054 0.083 Uiso 1 1 calc R . . H26C H 0.0955 0.8701 0.1246 0.083 Uiso 1 1 calc R . . C1 C 0.4904(3) 0.6576(5) 0.0441(5) 0.0332(13) Uani 1 1 d U . . H1B H 0.4994 0.6086 0.1107 0.040 Uiso 1 1 calc R . . H1C H 0.4795 0.6038 -0.0197 0.040 Uiso 1 1 calc R . . C2 C 0.5703(3) 0.7612(5) -0.0281(5) 0.0370(14) Uani 1 1 d U . . H2A H 0.5479 0.7361 -0.1020 0.044 Uiso 1 1 calc R . . C3 C 0.5963(3) 0.7835(6) 0.1478(5) 0.0431(15) Uani 1 1 d U . . H3A H 0.5947 0.7758 0.2195 0.052 Uiso 1 1 calc R . . C4 C 0.6405(3) 0.8521(6) 0.1188(5) 0.0441(15) Uani 1 1 d U . . H4A H 0.6762 0.9012 0.1660 0.053 Uiso 1 1 calc R . . C5 C 0.6597(3) 0.8953(5) -0.0612(4) 0.0403(14) Uani 1 1 d DU . . C8 C 0.7332(3) 0.8471(6) -0.0219(5) 0.0572(19) Uani 1 1 d DU . . H8A H 0.7570 0.8678 0.0556 0.086 Uiso 1 1 calc R . . H8B H 0.7586 0.8814 -0.0657 0.086 Uiso 1 1 calc R . . H8C H 0.7317 0.7609 -0.0300 0.086 Uiso 1 1 calc R . . C7 C 0.6197(3) 0.8656(6) -0.1812(4) 0.0548(18) Uani 1 1 d DU . . H7A H 0.6218 0.7802 -0.1922 0.082 Uiso 1 1 calc R . . H7B H 0.6406 0.9075 -0.2276 0.082 Uiso 1 1 calc R . . H7C H 0.5709 0.8899 -0.2009 0.082 Uiso 1 1 calc R . . C6 C 0.6578(4) 1.0278(5) -0.0414(6) 0.065(2) Uani 1 1 d DU . . H6A H 0.6839 1.0450 0.0361 0.097 Uiso 1 1 calc R . . H6B H 0.6093 1.0535 -0.0605 0.097 Uiso 1 1 calc R . . H6C H 0.6791 1.0701 -0.0872 0.097 Uiso 1 1 calc R . . O1S O 0.4130(3) 0.5866(5) -0.3597(4) 0.0706(14) Uani 1 1 d . . . O2S O 0.4019(3) 0.6704(5) 0.4311(5) 0.0861(17) Uani 1 1 d . . . O3S O 0.4908(3) 0.6925(5) 0.3174(4) 0.0744(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2 0.0699(12) 0.0510(10) 0.0402(8) 0.0033(8) 0.0103(7) -0.0162(9) Cl1 0.0500(9) 0.0548(10) 0.0420(8) 0.0007(7) 0.0152(7) 0.0067(8) O1 0.058(3) 0.037(2) 0.073(3) -0.013(2) 0.042(2) 0.000(2) N3 0.041(3) 0.026(2) 0.048(3) 0.006(2) 0.021(2) -0.004(2) N4 0.039(3) 0.030(3) 0.044(3) 0.009(2) 0.016(2) 0.001(2) N1 0.036(3) 0.035(3) 0.050(3) 0.000(2) 0.023(2) -0.002(2) N2 0.038(3) 0.035(3) 0.048(3) -0.006(2) 0.025(2) -0.007(2) C11 0.030(3) 0.021(3) 0.041(3) 0.008(2) 0.016(2) 0.003(2) C12 0.071(4) 0.043(4) 0.063(4) 0.006(3) 0.034(3) -0.001(3) C13 0.103(6) 0.035(4) 0.092(6) 0.014(4) 0.047(5) 0.002(4) C14 0.113(7) 0.062(6) 0.078(5) 0.026(4) 0.055(5) 0.025(5) C15 0.075(5) 0.058(5) 0.056(4) 0.008(3) 0.033(3) 0.001(4) C16 0.058(4) 0.047(4) 0.065(4) 0.008(3) 0.034(3) 0.004(3) C10 0.039(2) 0.023(2) 0.050(3) -0.003(3) 0.023(2) 0.001(3) C21 0.038(3) 0.034(3) 0.053(4) -0.002(3) 0.023(3) -0.006(3) C22 0.039(3) 0.029(3) 0.049(4) 0.010(3) 0.028(3) 0.005(3) C23 0.036(3) 0.046(4) 0.044(3) 0.008(3) 0.015(3) -0.006(3) C24 0.040(4) 0.045(4) 0.048(4) 0.001(3) 0.019(3) -0.002(3) C25 0.039(4) 0.050(4) 0.054(4) 0.001(3) 0.023(3) 0.012(3) C28 0.045(4) 0.068(5) 0.039(3) 0.009(3) 0.013(3) 0.010(3) C27 0.068(5) 0.044(4) 0.073(5) 0.011(3) 0.020(4) 0.024(4) C26 0.032(4) 0.088(5) 0.049(4) -0.006(4) 0.018(3) 0.006(3) C1 0.036(3) 0.021(3) 0.051(4) -0.004(3) 0.026(3) 0.001(2) C2 0.035(3) 0.032(3) 0.044(4) -0.003(3) 0.015(3) 0.006(3) C3 0.040(3) 0.049(4) 0.041(3) -0.003(3) 0.015(3) -0.007(3) C4 0.044(4) 0.047(4) 0.040(4) -0.013(3) 0.013(3) -0.007(3) C5 0.045(4) 0.040(3) 0.041(3) -0.002(3) 0.021(3) -0.013(3) C8 0.049(4) 0.083(5) 0.051(4) -0.008(4) 0.031(3) -0.013(4) C7 0.054(4) 0.063(4) 0.056(4) 0.004(3) 0.030(3) -0.020(4) C6 0.076(5) 0.053(4) 0.067(5) 0.009(3) 0.027(4) -0.023(4) O1S 0.070(3) 0.077(4) 0.055(3) -0.011(2) 0.011(2) 0.014(3) O2S 0.091(4) 0.094(4) 0.080(4) -0.010(3) 0.039(3) -0.024(3) O3S 0.101(4) 0.065(3) 0.061(3) 0.009(2) 0.034(3) 0.021(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 O1 C10 1.433(8) . ? N3 C22 1.338(7) . ? N3 C23 1.382(8) . ? N3 C21 1.444(7) . ? N4 C22 1.325(7) . ? N4 C24 1.377(8) . ? N4 C25 1.518(7) . ? N1 C2 1.301(7) . ? N1 C3 1.373(8) . ? N1 C1 1.484(7) . ? N2 C2 1.338(7) . ? N2 C4 1.386(8) . ? N2 C5 1.494(7) . ? C11 C16 1.366(6) . ? C11 C12 1.381(6) . ? C11 C10 1.513(8) . ? C12 C13 1.382(7) . ? C13 C14 1.364(7) . ? C14 C15 1.365(7) . ? C15 C16 1.377(7) . ? C10 C1 1.531(8) . ? C10 C21 1.545(8) . ? C23 C24 1.337(8) . ? C25 C26 1.510(5) . ? C25 C28 1.520(6) . ? C25 C27 1.529(6) . ? C3 C4 1.346(9) . ? C5 C8 1.512(6) . ? C5 C6 1.522(6) . ? C5 C7 1.521(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 C22 N3 C23 108.2(5) . . ? C22 N3 C21 124.2(5) . . ? C23 N3 C21 127.5(5) . . ? C22 N4 C24 107.5(5) . . ? C22 N4 C25 126.4(5) . . ? C24 N4 C25 126.0(5) . . ? C2 N1 C3 109.0(5) . . ? C2 N1 C1 124.0(5) . . ? C3 N1 C1 125.9(5) . . ? C2 N2 C4 107.6(5) . . ? C2 N2 C5 126.8(5) . . ? C4 N2 C5 125.6(5) . . ? C16 C11 C12 121.7(5) . . ? C16 C11 C10 118.9(4) . . ? C12 C11 C10 119.3(4) . . ? C11 C12 C13 117.9(5) . . ? C14 C13 C12 121.3(6) . . ? C13 C14 C15 119.4(7) . . ? C14 C15 C16 121.1(6) . . ? C11 C16 C15 118.7(5) . . ? O1 C10 C11 107.6(4) . . ? O1 C10 C1 109.4(5) . . ? C11 C10 C1 109.3(4) . . ? O1 C10 C21 110.1(5) . . ? C11 C10 C21 112.7(5) . . ? C1 C10 C21 107.6(4) . . ? N3 C21 C10 109.1(5) . . ? N4 C22 N3 109.1(5) . . ? C24 C23 N3 106.5(6) . . ? C23 C24 N4 108.6(6) . . ? C26 C25 N4 106.4(4) . . ? C26 C25 C28 111.9(4) . . ? N4 C25 C28 108.9(4) . . ? C26 C25 C27 112.3(4) . . ? N4 C25 C27 106.7(5) . . ? C28 C25 C27 110.4(4) . . ? N1 C1 C10 111.3(4) . . ? N1 C2 N2 109.4(5) . . ? C4 C3 N1 107.3(5) . . ? C3 C4 N2 106.7(6) . . ? N2 C5 C8 106.6(4) . . ? N2 C5 C6 106.5(5) . . ? C8 C5 C6 112.3(4) . . ? N2 C5 C7 108.2(4) . . ? C8 C5 C7 112.0(4) . . ? C6 C5 C7 110.8(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 C16 C11 C12 C13 0.1(3) . . . . ? C10 C11 C12 C13 176.2(5) . . . . ? C11 C12 C13 C14 0.0(3) . . . . ? C12 C13 C14 C15 0.0(6) . . . . ? C13 C14 C15 C16 -0.1(7) . . . . ? C12 C11 C16 C15 -0.2(5) . . . . ? C10 C11 C16 C15 -176.4(5) . . . . ? C14 C15 C16 C11 0.2(7) . . . . ? C16 C11 C10 O1 -175.1(4) . . . . ? C12 C11 C10 O1 8.7(6) . . . . ? C16 C11 C10 C1 66.2(6) . . . . ? C12 C11 C10 C1 -110.0(5) . . . . ? C16 C11 C10 C21 -53.4(6) . . . . ? C12 C11 C10 C21 130.4(4) . . . . ? C22 N3 C21 C10 -90.2(6) . . . . ? C23 N3 C21 C10 84.3(7) . . . . ? O1 C10 C21 N3 57.1(6) . . . . ? C11 C10 C21 N3 -63.2(6) . . . . ? C1 C10 C21 N3 176.3(4) . . . . ? C24 N4 C22 N3 1.2(6) . . . . ? C25 N4 C22 N3 177.8(5) . . . . ? C23 N3 C22 N4 0.1(6) . . . . ? C21 N3 C22 N4 175.5(4) . . . . ? C22 N3 C23 C24 -1.4(6) . . . . ? C21 N3 C23 C24 -176.6(5) . . . . ? N3 C23 C24 N4 2.2(6) . . . . ? C22 N4 C24 C23 -2.1(6) . . . . ? C25 N4 C24 C23 -178.7(5) . . . . ? C22 N4 C25 C26 -112.4(6) . . . . ? C24 N4 C25 C26 63.6(6) . . . . ? C22 N4 C25 C28 8.4(7) . . . . ? C24 N4 C25 C28 -175.6(5) . . . . ? C22 N4 C25 C27 127.6(6) . . . . ? C24 N4 C25 C27 -56.5(7) . . . . ? C2 N1 C1 C10 -87.5(6) . . . . ? C3 N1 C1 C10 79.1(7) . . . . ? O1 C10 C1 N1 -64.9(6) . . . . ? C11 C10 C1 N1 52.8(6) . . . . ? C21 C10 C1 N1 175.5(4) . . . . ? C3 N1 C2 N2 1.5(6) . . . . ? C1 N1 C2 N2 170.0(5) . . . . ? C4 N2 C2 N1 -1.0(6) . . . . ? C5 N2 C2 N1 178.4(5) . . . . ? C2 N1 C3 C4 -1.4(7) . . . . ? C1 N1 C3 C4 -169.6(5) . . . . ? N1 C3 C4 N2 0.7(7) . . . . ? C2 N2 C4 C3 0.1(7) . . . . ? C5 N2 C4 C3 -179.2(5) . . . . ? C2 N2 C5 C8 -113.7(6) . . . . ? C4 N2 C5 C8 65.5(6) . . . . ? C2 N2 C5 C6 126.2(6) . . . . ? C4 N2 C5 C6 -54.6(7) . . . . ? C2 N2 C5 C7 7.0(7) . . . . ? C4 N2 C5 C7 -173.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.786 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.078 #===END data_j-CUPHIM _database_code_CSD 169966 _exptl_special_details ; Crystals were grown at 298K from a concentrated dichloromethane solution. A crystal was mounted in a film of RS3000 perfluoropolyether on a dual-stage glass fibre and transferred to the diffractometer. ; _refine_special_details ; Positional disorder in one tert-butyl group was identified and modelled, with the larger component atoms refined as anisotropic. H atoms on disordered atoms were not placed. Other H atoms were placed geometrically. A SQUEEZE routine was used to eliminate a highly disordered molecule of solvent from the lattice. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H31 Cu N4 O' _chemical_formula_sum 'C23 H31 Cu N4 O' _chemical_formula_weight 443.06 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 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 21.330(2) _cell_length_b 12.2341(13) _cell_length_c 25.177(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.377(2) _cell_angle_gamma 90.00 _cell_volume 6075.3(15) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1568 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 19.6 _exptl_crystal_description tablet _exptl_crystal_colour 'deep red' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.969 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 0.734 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.8854 _exptl_absorpt_correction_T_max 0.9369 _exptl_absorpt_process_details 'SAINT v6.02a; SADABS v2.03 (Bruker, 2001)' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16436 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5347 _reflns_number_gt 3738 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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; PLATON (Spek, 2000)' _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^+8.3813P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary 'difference Fourier' _atom_sites_solution_hydrogens 'placed geometrically' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5347 _refine_ls_number_parameters 279 _refine_ls_number_restraints 134 _refine_ls_R_factor_all 0.0811 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1565 _refine_ls_wR_factor_gt 0.1464 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.105 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.80611(2) 0.28392(4) 0.558299(18) 0.03683(18) Uani 1 1 d U . . O1 O 0.72002(13) 0.2079(2) 0.52510(10) 0.0404(7) Uani 1 1 d U . . C1 C 0.6640(2) 0.0358(4) 0.51469(17) 0.0646(14) Uani 1 1 d DU . . H1A H 0.6985 0.0057 0.5012 0.078 Uiso 1 1 calc R . . H1B H 0.6508 -0.0225 0.5357 0.078 Uiso 1 1 calc R . . N1 N 0.89531(19) 0.4286(3) 0.53448(16) 0.0690(14) Uani 1 1 d DU . . C3 C 0.9612(2) 0.4622(5) 0.5455(2) 0.099(3) Uani 1 1 d DU . . H3A H 0.9743 0.5229 0.5286 0.119 Uiso 1 1 calc R . . C4 C 1.0025(3) 0.3939(5) 0.5842(2) 0.095(2) Uani 1 1 d DU . . H4A H 1.0507 0.3973 0.6005 0.114 Uiso 1 1 calc R . . N2 N 0.96188(17) 0.3164(3) 0.59615(15) 0.0608(12) Uani 1 1 d DU . . C2 C 0.8957(2) 0.3385(4) 0.56645(17) 0.0536(12) Uani 1 1 d DU . . C5 C 0.9926(2) 0.2158(4) 0.63302(17) 0.0614(13) Uani 1 1 d DU . . C6 C 1.0307(3) 0.1537(5) 0.6035(2) 0.0812(16) Uani 1 1 d DU . . H6A H 0.9990 0.1283 0.5659 0.122 Uiso 1 1 calc R . . H6B H 1.0533 0.0906 0.6270 0.122 Uiso 1 1 calc R . . H6C H 1.0647 0.2015 0.5982 0.122 Uiso 1 1 calc R . . C7 C 0.9373(2) 0.1472(4) 0.6398(2) 0.0667(15) Uani 1 1 d DU . . H7A H 0.9064 0.1216 0.6019 0.100 Uiso 1 1 calc R . . H7B H 0.9120 0.1912 0.6574 0.100 Uiso 1 1 calc R . . H7C H 0.9575 0.0841 0.6643 0.100 Uiso 1 1 calc R . . C8 C 1.0406(2) 0.2560(5) 0.69145(18) 0.0752(16) Uani 1 1 d DU . . H8A H 1.0609 0.1932 0.7162 0.113 Uiso 1 1 calc R . . H8B H 1.0155 0.3006 0.7090 0.113 Uiso 1 1 calc R . . H8C H 1.0765 0.3002 0.6868 0.113 Uiso 1 1 calc R . . C10 C 0.69396(19) 0.1330(4) 0.55491(15) 0.0510(11) Uani 1 1 d DU . . C11 C 0.64090(17) 0.1887(4) 0.57316(12) 0.0636(13) Uani 1 1 d DU . . C12 C 0.6114(2) 0.1304(5) 0.60604(19) 0.0789(17) Uani 1 1 d DU . . H12A H 0.6237 0.0564 0.6164 0.095 Uiso 1 1 calc R . . C13 C 0.5641(3) 0.1817(7) 0.6233(2) 0.099(2) Uani 1 1 d DU . . H13A H 0.5447 0.1424 0.6459 0.119 Uiso 1 1 calc R . . C14 C 0.5449(3) 0.2875(7) 0.6084(2) 0.107(2) Uani 1 1 d DU . . H14A H 0.5126 0.3211 0.6207 0.128 Uiso 1 1 calc R . . C15 C 0.5723(3) 0.3455(6) 0.5756(2) 0.102(2) Uani 1 1 d DU . . H15A H 0.5586 0.4188 0.5648 0.123 Uiso 1 1 calc R . . C16 C 0.6205(2) 0.2956(5) 0.55818(18) 0.0763(16) Uani 1 1 d DU . . H16A H 0.6396 0.3359 0.5357 0.092 Uiso 1 1 calc R . . C21 C 0.7537(2) 0.0932(4) 0.60791(16) 0.0521(12) Uani 1 1 d DU . . H21A H 0.7389 0.0325 0.6264 0.063 Uiso 1 1 calc R . . H21B H 0.7904 0.0660 0.5964 0.063 Uiso 1 1 calc R . . N3 N 0.77841(16) 0.1840(3) 0.64804(13) 0.0472(9) Uani 1 1 d DU . . C23 C 0.7710(2) 0.1949(6) 0.70064(18) 0.0763(17) Uani 1 1 d DU . . H23A H 0.7562 0.1398 0.7198 0.092 Uiso 1 1 calc R . . C24 C 0.7882(3) 0.2960(6) 0.7188(2) 0.0848(18) Uani 1 1 d DU A . H24A H 0.7895 0.3257 0.7540 0.102 Uiso 1 1 calc R . . N4 N 0.8042(2) 0.3515(3) 0.67727(15) 0.0643(11) Uani 1 1 d DU . . C22 C 0.7977(2) 0.2815(4) 0.63338(16) 0.0440(9) Uani 1 1 d DU A . C25 C 0.8286(4) 0.4758(6) 0.6766(3) 0.068(2) Uani 0.654(8) 1 d PDU A 1 C26 C 0.8232(7) 0.5352(9) 0.7264(5) 0.114(4) Uani 0.654(8) 1 d PDU A 1 H26A H 0.8531 0.5008 0.7622 0.171 Uiso 0.654(8) 1 calc PR A 1 H26B H 0.7763 0.5323 0.7239 0.171 Uiso 0.654(8) 1 calc PR A 1 H26C H 0.8367 0.6116 0.7257 0.171 Uiso 0.654(8) 1 calc PR A 1 C27 C 0.7818(5) 0.5241(8) 0.6196(4) 0.089(3) Uani 0.654(8) 1 d PDU A 1 H27A H 0.7858 0.4817 0.5880 0.134 Uiso 0.654(8) 1 calc PR A 1 H27B H 0.7947 0.6001 0.6169 0.134 Uiso 0.654(8) 1 calc PR A 1 H27C H 0.7349 0.5214 0.6172 0.134 Uiso 0.654(8) 1 calc PR A 1 C28 C 0.9008(4) 0.4853(8) 0.6787(5) 0.097(3) Uani 0.654(8) 1 d PDU A 1 H28A H 0.9045 0.4454 0.6463 0.146 Uiso 0.654(8) 1 calc PR A 1 H28B H 0.9325 0.4542 0.7148 0.146 Uiso 0.654(8) 1 calc PR A 1 H28C H 0.9118 0.5625 0.6764 0.146 Uiso 0.654(8) 1 calc PR A 1 C251 C 0.7952(5) 0.4529(9) 0.6829(4) 0.040(3) Uiso 0.346(8) 1 d PDU A 2 C261 C 0.8424(7) 0.4851(13) 0.7423(5) 0.053(4) Uiso 0.346(8) 1 d PDU A 2 H26D H 0.8891 0.4662 0.7476 0.079 Uiso 0.346(8) 1 calc PR A 2 H26E H 0.8298 0.4461 0.7707 0.079 Uiso 0.346(8) 1 calc PR A 2 H26F H 0.8392 0.5641 0.7474 0.079 Uiso 0.346(8) 1 calc PR A 2 C271 C 0.8190(8) 0.5031(14) 0.6382(6) 0.060(4) Uiso 0.346(8) 1 d PDU A 2 H27D H 0.8665 0.4834 0.6473 0.090 Uiso 0.346(8) 1 calc PR A 2 H27E H 0.8148 0.5828 0.6388 0.090 Uiso 0.346(8) 1 calc PR A 2 H27F H 0.7909 0.4754 0.6000 0.090 Uiso 0.346(8) 1 calc PR A 2 C281 C 0.7258(5) 0.4974(12) 0.6720(6) 0.059(4) Uiso 0.346(8) 1 d PDU A 2 H28D H 0.7119 0.4753 0.7033 0.089 Uiso 0.346(8) 1 calc PR A 2 H28E H 0.6935 0.4685 0.6355 0.089 Uiso 0.346(8) 1 calc PR A 2 H28F H 0.7268 0.5774 0.6701 0.089 Uiso 0.346(8) 1 calc PR A 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 0.0433(3) 0.0396(3) 0.0217(2) 0.0026(2) 0.00577(19) -0.0160(2) O1 0.0407(14) 0.0509(17) 0.0258(13) 0.0086(12) 0.0085(11) -0.0213(13) C1 0.064(3) 0.065(3) 0.043(2) 0.029(2) -0.004(2) -0.037(2) N1 0.061(2) 0.077(3) 0.044(2) 0.030(2) -0.0096(18) -0.043(2) C3 0.068(3) 0.131(5) 0.064(3) 0.049(4) -0.013(3) -0.064(4) C4 0.061(3) 0.129(5) 0.069(4) 0.055(4) -0.005(3) -0.051(3) N2 0.046(2) 0.080(3) 0.041(2) 0.0259(19) -0.0013(17) -0.0339(19) C2 0.052(2) 0.062(3) 0.031(2) 0.016(2) -0.0020(19) -0.032(2) C5 0.041(2) 0.088(4) 0.044(2) 0.029(2) 0.0030(19) -0.019(2) C6 0.065(3) 0.122(5) 0.054(3) 0.024(3) 0.020(3) -0.009(3) C7 0.044(3) 0.076(4) 0.069(3) 0.039(3) 0.009(2) -0.011(2) C8 0.058(3) 0.101(4) 0.044(3) 0.028(3) -0.005(2) -0.016(3) C10 0.043(2) 0.070(3) 0.033(2) 0.021(2) 0.0065(18) -0.026(2) C11 0.040(2) 0.113(4) 0.028(2) 0.027(2) 0.0021(18) -0.022(2) C12 0.039(3) 0.143(5) 0.042(3) 0.026(3) 0.001(2) -0.040(3) C13 0.050(3) 0.201(7) 0.042(3) 0.016(4) 0.013(3) -0.045(4) C14 0.057(3) 0.212(8) 0.049(3) 0.022(5) 0.017(3) -0.006(4) C15 0.089(4) 0.172(7) 0.055(3) 0.038(4) 0.039(3) 0.032(4) C16 0.059(3) 0.129(5) 0.040(3) 0.028(3) 0.019(2) 0.004(3) C21 0.048(2) 0.068(3) 0.033(2) 0.021(2) 0.0074(19) -0.025(2) N3 0.0336(17) 0.078(3) 0.0243(16) 0.0125(16) 0.0044(14) -0.0051(17) C23 0.035(2) 0.165(6) 0.026(2) 0.030(3) 0.008(2) -0.002(3) C24 0.062(3) 0.162(6) 0.026(2) 0.002(3) 0.011(2) 0.029(4) N4 0.071(3) 0.078(3) 0.0281(19) -0.0015(18) 0.0013(18) 0.032(2) C22 0.048(2) 0.052(2) 0.0258(18) 0.0038(19) 0.0075(17) 0.006(2) C25 0.063(5) 0.067(5) 0.057(5) -0.013(4) 0.003(4) 0.000(4) C26 0.187(13) 0.073(7) 0.101(7) -0.028(6) 0.077(9) -0.025(8) C27 0.092(7) 0.068(6) 0.092(6) 0.008(5) 0.018(6) -0.003(5) C28 0.086(6) 0.061(6) 0.130(9) -0.010(6) 0.025(6) -0.014(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 O1 1.941(2) . ? Cu1 O1 1.959(2) 7_656 ? Cu1 C2 1.960(4) . ? Cu1 C22 1.966(4) . ? Cu1 Cu1 3.1122(9) 7_656 ? O1 C10 1.424(4) . ? O1 Cu1 1.959(2) 7_656 ? C1 N1 1.459(5) 7_656 ? C1 C10 1.535(5) . ? N1 C2 1.364(5) . ? N1 C3 1.386(5) . ? N1 C1 1.459(5) 7_656 ? C3 C4 1.331(7) . ? C4 N2 1.393(5) . ? N2 C2 1.349(5) . ? N2 C5 1.531(5) . ? C5 C6 1.501(5) . ? C5 C7 1.509(5) . ? C5 C8 1.520(5) . ? C10 C21 1.532(5) . ? C10 C11 1.533(6) . ? C11 C16 1.385(7) . ? C11 C12 1.410(5) . ? C12 C13 1.391(7) . ? C13 C14 1.366(11) . ? C14 C15 1.377(7) . ? C15 C16 1.402(7) . ? C21 N3 1.458(6) . ? N3 C22 1.359(6) . ? N3 C23 1.399(5) . ? C23 C24 1.321(7) . ? C24 N4 1.392(5) . ? N4 C251 1.272(12) . ? N4 C22 1.363(5) . ? N4 C25 1.610(8) . ? C25 C26 1.490(8) . ? C25 C27 1.522(8) . ? C25 C28 1.525(8) . ? C251 C281 1.502(9) . ? C251 C261 1.504(9) . ? C251 C271 1.526(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 74.12(11) . 7_656 ? O1 Cu1 C2 158.94(16) . . ? O1 Cu1 C2 87.88(14) 7_656 . ? O1 Cu1 C22 89.40(15) . . ? O1 Cu1 C22 159.81(14) 7_656 . ? C2 Cu1 C22 110.27(18) . . ? O1 Cu1 Cu1 37.27(7) . 7_656 ? O1 Cu1 Cu1 36.86(7) 7_656 7_656 ? C2 Cu1 Cu1 123.96(13) . 7_656 ? C22 Cu1 Cu1 125.75(13) . 7_656 ? C10 O1 Cu1 125.2(2) . . ? C10 O1 Cu1 126.1(2) . 7_656 ? Cu1 O1 Cu1 105.88(11) . 7_656 ? N1 C1 C10 109.7(4) 7_656 . ? C2 N1 C3 110.1(4) . . ? C2 N1 C1 123.4(3) . 7_656 ? C3 N1 C1 124.5(3) . 7_656 ? C4 C3 N1 107.5(4) . . ? C3 C4 N2 106.9(4) . . ? C2 N2 C4 110.5(4) . . ? C2 N2 C5 127.8(3) . . ? C4 N2 C5 121.4(4) . . ? N2 C2 N1 105.0(3) . . ? N2 C2 Cu1 139.7(3) . . ? N1 C2 Cu1 115.3(3) . . ? C6 C5 C7 111.6(4) . . ? C6 C5 C8 110.5(4) . . ? C7 C5 C8 109.8(4) . . ? C6 C5 N2 107.1(4) . . ? C7 C5 N2 110.1(3) . . ? C8 C5 N2 107.6(4) . . ? O1 C10 C21 107.5(3) . . ? O1 C10 C11 110.7(3) . . ? C21 C10 C11 110.1(3) . . ? O1 C10 C1 107.4(3) . . ? C21 C10 C1 109.1(4) . . ? C11 C10 C1 111.9(3) . . ? C16 C11 C12 118.3(5) . . ? C16 C11 C10 121.9(3) . . ? C12 C11 C10 119.8(5) . . ? C13 C12 C11 119.6(5) . . ? C14 C13 C12 121.3(5) . . ? C13 C14 C15 120.1(6) . . ? C14 C15 C16 119.6(6) . . ? C11 C16 C15 121.1(5) . . ? N3 C21 C10 108.9(4) . . ? C22 N3 C23 109.2(4) . . ? C22 N3 C21 123.2(3) . . ? C23 N3 C21 126.0(4) . . ? C24 C23 N3 107.4(4) . . ? C23 C24 N4 108.2(4) . . ? C251 N4 C22 136.9(6) . . ? C251 N4 C24 107.6(6) . . ? C22 N4 C24 108.9(4) . . ? C251 N4 C25 30.9(5) . . ? C22 N4 C25 121.2(4) . . ? C24 N4 C25 129.8(5) . . ? N3 C22 N4 106.2(4) . . ? N3 C22 Cu1 115.0(3) . . ? N4 C22 Cu1 138.8(4) . . ? C26 C25 C27 111.8(8) . . ? C26 C25 C28 109.5(7) . . ? C27 C25 C28 107.1(7) . . ? C26 C25 N4 108.9(7) . . ? C27 C25 N4 106.1(5) . . ? C28 C25 N4 113.5(6) . . ? N4 C251 C281 120.8(10) . . ? N4 C251 C261 107.1(9) . . ? C281 C251 C261 109.0(9) . . ? N4 C251 C271 101.9(9) . . ? C281 C251 C271 107.5(9) . . ? C261 C251 C271 110.1(9) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.467 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.072 #===END