data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H32 Cu2 N10 O3' _chemical_formula_weight 683.74 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 22.7268(19) _cell_length_b 9.5719(7) _cell_length_c 14.6305(11) _cell_angle_alpha 90.00 _cell_angle_beta 112.744(9) _cell_angle_gamma 90.00 _cell_volume 2935.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max .3 _exptl_crystal_size_mid .2 _exptl_crystal_size_min .1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 1.498 _exptl_absorpt_correction_type 'MULTI-SCAN' _exptl_absorpt_correction_T_min 0.684 _exptl_absorpt_correction_T_max 0.791 _exptl_absorpt_process_details '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 'BRUKER SMART APEX II' _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 18115 _diffrn_reflns_av_R_equivalents 0.0956 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 24.03 _reflns_number_total 2314 _reflns_number_gt 1696 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0846P)^2^+6.1119P] 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 2314 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1525 _refine_ls_wR_factor_gt 0.1345 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.017 _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 Cu01 Cu 0.02445(3) 0.16289(6) 0.50887(4) 0.0512(3) Uani 1 1 d . . . O1 O -0.04178(18) 0.2308(4) 0.5467(3) 0.0637(10) Uani 1 1 d . . . N2 N 0.0126(2) 0.3190(4) 0.4194(3) 0.0510(10) Uani 1 1 d . . . O2 O 0.0000 0.3388(6) 0.7500 0.0714(16) Uani 1 2 d S . . N3 N 0.0432(2) 0.0100(5) 0.6071(3) 0.0658(12) Uani 1 1 d . . . C5 C -0.0893(2) 0.3981(5) 0.4157(3) 0.0463(11) Uani 1 1 d . . . N1 N 0.1010(2) 0.1188(5) 0.4751(3) 0.0610(12) Uani 1 1 d . . . H1 H 0.0904(9) 0.067(4) 0.432(3) 0.073 Uiso 1 1 calc R . . C6 C -0.1448(2) 0.4830(5) 0.3624(3) 0.0517(12) Uani 1 1 d . . . C4 C -0.0355(2) 0.4026(5) 0.3888(3) 0.0493(12) Uani 1 1 d . . . H4 H -0.0350 0.4726 0.3450 0.059 Uiso 1 1 calc R . . C14 C -0.0893(2) 0.3115(5) 0.4944(4) 0.0515(12) Uani 1 1 d . . . C10 C -0.2537(3) 0.5556(7) 0.3356(5) 0.0709(16) Uani 1 1 d . . . H10 H -0.2894 0.5476 0.3516 0.085 Uiso 1 1 calc R . . C13 C -0.1437(3) 0.3108(6) 0.5187(4) 0.0646(15) Uani 1 1 d . . . H13 H -0.1435 0.2562 0.5714 0.077 Uiso 1 1 calc R . . N4 N 0.0644(2) 0.0205(5) 0.6933(3) 0.0683(13) Uani 1 1 d . . . C11 C -0.1986(2) 0.4748(5) 0.3873(4) 0.0561(13) Uani 1 1 d . . . C3 C 0.0630(3) 0.3301(6) 0.3802(5) 0.0697(16) Uani 1 1 d . . . H3A H 0.0470 0.2965 0.3124 0.084 Uiso 1 1 calc R . . H3B H 0.0752 0.4272 0.3801 0.084 Uiso 1 1 calc R . . C12 C -0.1961(3) 0.3875(6) 0.4672(4) 0.0634(14) Uani 1 1 d . . . H12 H -0.2313 0.3829 0.4846 0.076 Uiso 1 1 calc R . . C8 C -0.2018(3) 0.6571(7) 0.2393(5) 0.0772(18) Uani 1 1 d . . . H8 H -0.2027 0.7197 0.1902 0.093 Uiso 1 1 calc R . . C7 C -0.1476(3) 0.5788(6) 0.2867(4) 0.0640(15) Uani 1 1 d . . . H7 H -0.1126 0.5888 0.2691 0.077 Uiso 1 1 calc R . . C9 C -0.2546(3) 0.6451(7) 0.2627(5) 0.0732(17) Uani 1 1 d . . . H9 H -0.2909 0.6979 0.2289 0.088 Uiso 1 1 calc R . . N5 N 0.0850(3) 0.0271(8) 0.7780(4) 0.117(2) Uani 1 1 d . . . C1 C 0.1592(3) 0.0649(9) 0.5523(5) 0.102(3) Uani 1 1 d . . . H1A H 0.1504 -0.0236 0.5752 0.153 Uiso 1 1 calc R . . H1B H 0.1738 0.1296 0.6066 0.153 Uiso 1 1 calc R . . H1C H 0.1915 0.0533 0.5259 0.153 Uiso 1 1 calc R . . C2 C 0.1180(4) 0.2489(8) 0.4400(7) 0.117(3) Uani 1 1 d . . . H2A H 0.1443 0.3043 0.4966 0.141 Uiso 1 1 calc R . . H2B H 0.1432 0.2279 0.4012 0.141 Uiso 1 1 calc R . . H2 H 0.030(5) 0.295(11) 0.760(10) 0.21(5) 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 Cu01 0.0630(5) 0.0509(4) 0.0382(4) 0.0036(3) 0.0179(3) 0.0036(3) O1 0.078(2) 0.070(2) 0.052(2) 0.0203(19) 0.0346(19) 0.018(2) N2 0.059(2) 0.052(3) 0.046(2) 0.0044(19) 0.025(2) 0.004(2) O2 0.087(5) 0.063(4) 0.061(4) 0.000 0.025(3) 0.000 N3 0.088(3) 0.064(3) 0.037(3) 0.003(2) 0.015(2) 0.000(3) C5 0.059(3) 0.046(3) 0.034(2) -0.003(2) 0.019(2) -0.001(2) N1 0.069(3) 0.054(3) 0.059(3) -0.003(2) 0.022(2) 0.008(2) C6 0.062(3) 0.049(3) 0.042(3) -0.005(2) 0.018(2) 0.003(2) C4 0.064(3) 0.043(3) 0.043(3) 0.005(2) 0.023(2) 0.003(3) C14 0.063(3) 0.054(3) 0.041(3) -0.005(2) 0.024(2) 0.001(3) C10 0.059(3) 0.076(4) 0.072(4) -0.015(3) 0.019(3) 0.003(3) C13 0.088(4) 0.060(3) 0.058(3) 0.004(3) 0.042(3) 0.000(3) N4 0.060(3) 0.097(4) 0.047(3) 0.009(3) 0.020(2) 0.013(3) C11 0.057(3) 0.054(3) 0.057(3) -0.014(3) 0.022(2) -0.003(3) C3 0.069(4) 0.073(4) 0.074(4) 0.025(3) 0.036(3) 0.012(3) C12 0.063(3) 0.067(3) 0.071(4) -0.010(3) 0.037(3) -0.009(3) C8 0.088(4) 0.084(5) 0.060(4) 0.013(3) 0.029(3) 0.027(3) C7 0.073(3) 0.072(4) 0.050(3) 0.009(3) 0.028(3) 0.016(3) C9 0.069(4) 0.075(4) 0.066(4) 0.001(3) 0.015(3) 0.020(3) N5 0.102(4) 0.198(7) 0.042(3) 0.010(4) 0.019(3) 0.031(5) C1 0.068(4) 0.146(7) 0.077(5) -0.033(5) 0.011(3) 0.012(4) C2 0.129(6) 0.095(6) 0.169(8) 0.037(6) 0.102(6) 0.036(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 Cu01 O1 1.907(3) . ? Cu01 N2 1.936(4) . ? Cu01 N3 1.979(4) . ? Cu01 N1 2.029(4) . ? Cu01 N3 2.442(5) 5_556 ? O1 C14 1.307(6) . ? N2 C4 1.287(6) . ? N2 C3 1.470(7) . ? N3 N4 1.167(6) . ? N3 Cu01 2.442(5) 5_556 ? C5 C14 1.419(7) . ? C5 C4 1.422(6) . ? C5 C6 1.450(7) . ? N1 C2 1.455(9) . ? N1 C1 1.461(8) . ? C6 C11 1.406(7) . ? C6 C7 1.420(7) . ? C14 C13 1.412(7) . ? C10 C9 1.361(8) . ? C10 C11 1.416(8) . ? C13 C12 1.353(8) . ? N4 N5 1.145(7) . ? C11 C12 1.420(8) . ? C3 C2 1.445(9) . ? C8 C9 1.373(9) . ? C8 C7 1.379(8) . ? 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 Cu01 N2 90.78(16) . . ? O1 Cu01 N3 90.81(17) . . ? N2 Cu01 N3 175.41(18) . . ? O1 Cu01 N1 171.49(18) . . ? N2 Cu01 N1 84.49(17) . . ? N3 Cu01 N1 93.39(19) . . ? O1 Cu01 N3 94.40(16) . 5_556 ? N2 Cu01 N3 99.65(16) . 5_556 ? N3 Cu01 N3 84.52(17) . 5_556 ? N1 Cu01 N3 93.37(18) . 5_556 ? C14 O1 Cu01 126.7(3) . . ? C4 N2 C3 120.3(4) . . ? C4 N2 Cu01 126.4(3) . . ? C3 N2 Cu01 113.2(3) . . ? N4 N3 Cu01 127.2(4) . . ? N4 N3 Cu01 134.0(4) . 5_556 ? Cu01 N3 Cu01 95.48(17) . 5_556 ? C14 C5 C4 120.8(4) . . ? C14 C5 C6 119.4(4) . . ? C4 C5 C6 119.8(4) . . ? C2 N1 C1 106.9(6) . . ? C2 N1 Cu01 106.1(4) . . ? C1 N1 Cu01 119.3(4) . . ? C11 C6 C7 117.2(5) . . ? C11 C6 C5 119.5(5) . . ? C7 C6 C5 123.2(4) . . ? N2 C4 C5 126.2(4) . . ? O1 C14 C13 117.1(5) . . ? O1 C14 C5 124.1(4) . . ? C13 C14 C5 118.8(5) . . ? C9 C10 C11 120.3(6) . . ? C12 C13 C14 121.7(5) . . ? N5 N4 N3 178.2(7) . . ? C6 C11 C10 120.6(5) . . ? C6 C11 C12 119.0(5) . . ? C10 C11 C12 120.4(5) . . ? C2 C3 N2 110.3(5) . . ? C13 C12 C11 121.6(5) . . ? C9 C8 C7 121.8(6) . . ? C8 C7 C6 120.3(5) . . ? C10 C9 C8 119.8(6) . . ? C3 C2 N1 112.8(6) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.03 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.900 _refine_diff_density_min -0.591 _refine_diff_density_rms 0.098 data_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 Cu2 N6 O4' _chemical_formula_weight 665.70 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2270(3) _cell_length_b 8.7076(4) _cell_length_c 11.0944(6) _cell_angle_alpha 84.120(4) _cell_angle_beta 86.489(4) _cell_angle_gamma 89.237(4) _cell_volume 693.17(6) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.595 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 342 _exptl_absorpt_coefficient_mu 1.583 _exptl_absorpt_correction_type 'MULTI-SCAN' _exptl_absorpt_correction_T_min 0.635 _exptl_absorpt_correction_T_max 0.711 _exptl_absorpt_process_details '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 'BRUKER SMART APEX II' _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 10161 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.68 _reflns_number_total 2617 _reflns_number_gt 1900 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0889P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2617 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0766 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1437 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.53544(7) 0.91404(6) 0.87617(5) 0.0414(2) Uani 1 1 d . . . O1 O 0.3435(4) 1.0349(4) 0.8003(3) 0.0445(7) Uani 1 1 d . . . N2 N 0.7049(5) 0.9539(4) 0.7364(3) 0.0402(8) Uani 1 1 d . . . N1 N 0.7597(5) 0.8164(5) 0.9573(3) 0.0499(10) Uani 1 1 d . . . H1 H 0.7653 0.8581 1.0290 0.060 Uiso 1 1 calc R . . N3 N 0.3682(5) 0.8410(5) 1.0125(4) 0.0563(11) Uani 1 1 d . . . C14 C 0.3558(6) 1.1226(5) 0.6970(4) 0.0401(10) Uani 1 1 d . . . C5 C 0.5136(6) 1.1327(5) 0.6148(4) 0.0368(9) Uani 1 1 d . . . C6 C 0.5115(6) 1.2371(5) 0.5039(4) 0.0432(11) Uani 1 1 d . . . C11 C 0.3508(7) 1.3250(5) 0.4798(4) 0.0483(11) Uani 1 1 d . . . C1 C 0.7583(8) 0.6487(6) 0.9867(6) 0.0730(16) Uani 1 1 d . . . H1A H 0.6479 0.6193 1.0357 0.110 Uiso 1 1 calc R . . H1B H 0.8651 0.6173 1.0307 0.110 Uiso 1 1 calc R . . H1C H 0.7610 0.5994 0.9131 0.110 Uiso 1 1 calc R . . C3 C 0.8828(6) 0.8749(6) 0.7491(4) 0.0472(11) Uani 1 1 d . . . H3A H 0.9791 0.9301 0.6980 0.057 Uiso 1 1 calc R . . H3B H 0.8761 0.7708 0.7258 0.057 Uiso 1 1 calc R . . C12 C 0.1962(6) 1.3101(6) 0.5631(5) 0.0545(13) Uani 1 1 d . . . H12 H 0.0900 1.3682 0.5467 0.065 Uiso 1 1 calc R . . C13 C 0.1975(6) 1.2132(6) 0.6671(4) 0.0498(12) Uani 1 1 d . . . H13 H 0.0922 1.2060 0.7199 0.060 Uiso 1 1 calc R . . C2 C 0.9241(6) 0.8710(6) 0.8814(4) 0.0559(13) Uani 1 1 d . . . H2A H 1.0283 0.8024 0.8983 0.067 Uiso 1 1 calc R . . H2B H 0.9565 0.9735 0.8996 0.067 Uiso 1 1 calc R . . C4 C 0.6777(6) 1.0456(5) 0.6391(4) 0.0426(11) Uani 1 1 d . . . H4 H 0.7746 1.0553 0.5797 0.051 Uiso 1 1 calc R . . O2 O 0.1710(5) 0.6891(5) 1.1501(4) 0.0807(12) Uani 1 1 d . . . C7 C 0.6619(7) 1.2550(6) 0.4174(4) 0.0550(13) Uani 1 1 d . . . H7 H 0.7688 1.1965 0.4300 0.066 Uiso 1 1 calc R . . C15 C 0.2738(6) 0.7631(6) 1.0776(4) 0.0494(12) Uani 1 1 d . . . C9 C 0.4962(8) 1.4454(6) 0.2939(5) 0.0645(15) Uani 1 1 d . . . H9 H 0.4923 1.5148 0.2245 0.077 Uiso 1 1 calc R . . C10 C 0.3501(8) 1.4304(6) 0.3738(4) 0.0574(13) Uani 1 1 d . . . H10 H 0.2451 1.4907 0.3594 0.069 Uiso 1 1 calc R . . C8 C 0.6549(8) 1.3562(6) 0.3154(5) 0.0639(14) Uani 1 1 d . . . H8 H 0.7567 1.3658 0.2597 0.077 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 0.0353(3) 0.0543(4) 0.0333(3) 0.0001(2) 0.0001(2) 0.0005(2) O1 0.0380(16) 0.058(2) 0.0355(17) 0.0025(15) 0.0045(13) 0.0029(14) N2 0.0369(19) 0.048(2) 0.036(2) -0.0052(17) -0.0022(15) 0.0037(16) N1 0.049(2) 0.060(3) 0.040(2) -0.0016(19) -0.0034(18) 0.0025(18) N3 0.043(2) 0.079(3) 0.042(2) 0.011(2) 0.0038(19) -0.005(2) C14 0.039(2) 0.044(3) 0.038(3) -0.008(2) -0.0029(19) 0.0043(18) C5 0.043(2) 0.041(2) 0.026(2) -0.0050(18) -0.0033(18) 0.0020(18) C6 0.052(3) 0.043(3) 0.036(2) -0.007(2) -0.007(2) 0.003(2) C11 0.056(3) 0.049(3) 0.041(3) -0.006(2) -0.010(2) 0.004(2) C1 0.062(3) 0.062(4) 0.093(5) 0.001(3) -0.007(3) 0.007(3) C3 0.037(2) 0.062(3) 0.042(3) -0.004(2) -0.001(2) 0.010(2) C12 0.043(3) 0.057(3) 0.063(3) 0.001(3) -0.008(2) 0.010(2) C13 0.038(2) 0.056(3) 0.053(3) 0.003(2) -0.001(2) 0.007(2) C2 0.039(3) 0.078(4) 0.051(3) -0.003(3) -0.008(2) 0.008(2) C4 0.044(2) 0.053(3) 0.031(2) -0.005(2) 0.0022(19) 0.003(2) O2 0.076(3) 0.078(3) 0.081(3) 0.011(2) 0.023(2) -0.010(2) C7 0.066(3) 0.057(3) 0.040(3) 0.003(2) 0.004(2) 0.011(2) C15 0.039(2) 0.061(3) 0.047(3) -0.002(3) -0.005(2) 0.007(2) C9 0.094(4) 0.058(3) 0.039(3) 0.010(3) -0.007(3) -0.001(3) C10 0.067(3) 0.059(3) 0.046(3) -0.001(3) -0.014(3) 0.005(3) C8 0.076(4) 0.068(4) 0.044(3) 0.000(3) 0.008(3) 0.002(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 1.914(3) . ? Cu1 N2 1.921(4) . ? Cu1 N3 1.937(4) . ? Cu1 N1 2.036(4) . ? O1 C14 1.310(5) . ? N2 C4 1.299(5) . ? N2 C3 1.458(5) . ? N1 C1 1.464(7) . ? N1 C2 1.469(6) . ? N3 C15 1.140(6) . ? C14 C5 1.414(6) . ? C14 C13 1.418(6) . ? C5 C4 1.424(6) . ? C5 C6 1.454(6) . ? C6 C7 1.404(6) . ? C6 C11 1.407(6) . ? C11 C12 1.405(6) . ? C11 C10 1.416(7) . ? C3 C2 1.512(6) . ? C12 C13 1.358(7) . ? O2 C15 1.203(6) . ? C7 C8 1.365(7) . ? C9 C10 1.335(7) . ? C9 C8 1.396(7) . ? 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 N2 92.28(13) . . ? O1 Cu1 N3 91.83(14) . . ? N2 Cu1 N3 171.26(17) . . ? O1 Cu1 N1 171.31(15) . . ? N2 Cu1 N1 84.61(14) . . ? N3 Cu1 N1 92.37(16) . . ? C14 O1 Cu1 127.8(3) . . ? C4 N2 C3 119.6(4) . . ? C4 N2 Cu1 126.8(3) . . ? C3 N2 Cu1 113.5(3) . . ? C1 N1 C2 112.9(4) . . ? C1 N1 Cu1 117.1(3) . . ? C2 N1 Cu1 106.7(3) . . ? C15 N3 Cu1 161.7(4) . . ? O1 C14 C5 124.9(4) . . ? O1 C14 C13 116.5(4) . . ? C5 C14 C13 118.6(4) . . ? C14 C5 C4 121.6(4) . . ? C14 C5 C6 119.7(4) . . ? C4 C5 C6 118.7(4) . . ? C7 C6 C11 117.3(4) . . ? C7 C6 C5 123.5(4) . . ? C11 C6 C5 119.1(4) . . ? C12 C11 C6 119.4(4) . . ? C12 C11 C10 121.3(4) . . ? C6 C11 C10 119.3(5) . . ? N2 C3 C2 106.4(3) . . ? C13 C12 C11 121.8(4) . . ? C12 C13 C14 121.5(4) . . ? N1 C2 C3 109.2(4) . . ? N2 C4 C5 126.1(4) . . ? C8 C7 C6 121.6(5) . . ? N3 C15 O2 175.8(6) . . ? C10 C9 C8 119.4(5) . . ? C9 C10 C11 121.8(5) . . ? C7 C8 C9 120.5(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.622 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.089 data_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H15 Cu N5 O' _chemical_formula_weight 356.88 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 P21/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 7.7783(5) _cell_length_b 12.6455(9) _cell_length_c 15.1497(9) _cell_angle_alpha 90.00 _cell_angle_beta 98.037(4) _cell_angle_gamma 90.00 _cell_volume 1475.50(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 732 _exptl_absorpt_coefficient_mu 1.492 _exptl_absorpt_correction_type 'MULTI-SCAN' _exptl_absorpt_correction_T_min 0.693 _exptl_absorpt_correction_T_max 0.779 _exptl_absorpt_process_details '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 'BRUKER SMART APEX II' _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 20106 _diffrn_reflns_av_R_equivalents 0.0798 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.75 _reflns_number_total 2814 _reflns_number_gt 1643 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.1214P)^2^+3.9956P] 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 2814 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1284 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.2487 _refine_ls_wR_factor_gt 0.2133 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.09078(12) 0.98053(8) 0.25735(6) 0.0550(4) Uani 1 1 d . . . N3 N 0.3059(8) 1.0305(6) 0.3335(4) 0.0586(18) Uani 1 1 d . . . O1 O 0.0643(6) 1.1113(4) 0.1934(3) 0.0545(14) Uani 1 1 d . . . N4 N 0.6034(8) 1.0375(6) 0.4074(4) 0.0607(19) Uani 1 1 d . . . N5 N -0.1297(10) 1.0205(6) 0.3421(5) 0.070(2) Uani 1 1 d . . . C15 C 0.4483(9) 1.0329(6) 0.3641(5) 0.0450(17) Uani 1 1 d . . . C16 C -0.2596(10) 1.0276(6) 0.3687(5) 0.0478(18) Uani 1 1 d . . . N1 N 0.1175(9) 0.8322(6) 0.3148(4) 0.0578(19) Uani 1 1 d . . . C1 C 0.1350(12) 0.8257(8) 0.4135(5) 0.074(3) Uani 1 1 d . . . H1A H 0.2334 0.8667 0.4391 0.110 Uiso 1 1 calc R . . H1B H 0.1511 0.7533 0.4318 0.110 Uiso 1 1 calc R . . H1C H 0.0318 0.8530 0.4334 0.110 Uiso 1 1 calc R . . C2 C -0.0301(10) 0.7693(7) 0.2720(5) 0.059(2) Uani 1 1 d . . . H2A H -0.1354 0.7894 0.2953 0.071 Uiso 1 1 calc R . . H2B H -0.0091 0.6947 0.2837 0.071 Uiso 1 1 calc R . . C3 C -0.0494(10) 0.7906(7) 0.1725(5) 0.054(2) Uani 1 1 d . . . H3A H 0.0453 0.7582 0.1469 0.065 Uiso 1 1 calc R . . H3B H -0.1580 0.7616 0.1431 0.065 Uiso 1 1 calc R . . N2 N -0.0466(7) 0.9046(5) 0.1611(4) 0.0488(16) Uani 1 1 d . . . C4 C -0.1309(9) 0.9472(7) 0.0909(5) 0.0488(19) Uani 1 1 d . . . H4 H -0.1904 0.9009 0.0498 0.059 Uiso 1 1 calc R . . C5 C -0.1441(9) 1.0550(6) 0.0689(4) 0.0455(17) Uani 1 1 d . . . C14 C -0.0464(9) 1.1327(6) 0.1225(5) 0.0465(18) Uani 1 1 d . . . C13 C -0.0682(10) 1.2407(7) 0.0979(5) 0.0514(19) Uani 1 1 d . . . H13 H -0.0045 1.2916 0.1327 0.062 Uiso 1 1 calc R . . C12 C -0.1787(10) 1.2721(7) 0.0256(5) 0.058(2) Uani 1 1 d . . . H12 H -0.1892 1.3437 0.0119 0.069 Uiso 1 1 calc R . . C11 C -0.2792(9) 1.1971(7) -0.0302(5) 0.0507(19) Uani 1 1 d . . . C10 C -0.3934(11) 1.2319(8) -0.1063(5) 0.065(2) Uani 1 1 d . . . H10 H -0.4041 1.3038 -0.1189 0.078 Uiso 1 1 calc R . . C9 C -0.4852(10) 1.1621(9) -0.1597(5) 0.065(2) Uani 1 1 d . . . H9 H -0.5614 1.1854 -0.2087 0.078 Uiso 1 1 calc R . . C8 C -0.4666(10) 1.0548(9) -0.1420(5) 0.066(2) Uani 1 1 d . . . H8 H -0.5293 1.0068 -0.1803 0.079 Uiso 1 1 calc R . . C7 C -0.3582(10) 1.0179(7) -0.0696(5) 0.057(2) Uani 1 1 d . . . H7 H -0.3488 0.9455 -0.0592 0.068 Uiso 1 1 calc R . . C6 C -0.2601(9) 1.0894(7) -0.0103(5) 0.0488(19) Uani 1 1 d . . . H1 H 0.207(8) 0.809(4) 0.302(4) 0.020(16) 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 0.0504(6) 0.0747(8) 0.0349(6) -0.0001(5) -0.0116(4) -0.0029(4) N3 0.045(4) 0.084(5) 0.044(4) -0.001(3) -0.007(3) -0.001(3) O1 0.047(3) 0.073(4) 0.039(3) -0.003(3) -0.013(2) -0.006(2) N4 0.038(4) 0.097(6) 0.044(4) -0.007(4) -0.006(3) 0.000(3) N5 0.052(5) 0.097(6) 0.057(5) -0.004(4) -0.002(4) -0.003(4) C15 0.046(5) 0.055(5) 0.033(4) 0.000(3) 0.001(3) -0.003(3) C16 0.042(5) 0.058(5) 0.038(4) 0.004(4) -0.015(3) -0.004(3) N1 0.037(4) 0.089(5) 0.046(4) 0.000(4) 0.002(3) 0.008(3) C1 0.081(6) 0.098(7) 0.036(5) 0.008(5) -0.011(4) 0.008(5) C2 0.059(5) 0.064(5) 0.049(5) 0.001(4) -0.012(4) -0.006(4) C3 0.045(4) 0.073(6) 0.046(5) -0.003(4) 0.007(3) 0.007(4) N2 0.048(3) 0.059(4) 0.037(4) -0.004(3) -0.001(3) 0.004(3) C4 0.042(4) 0.070(6) 0.032(4) -0.009(4) -0.001(3) -0.004(3) C5 0.046(4) 0.059(5) 0.029(4) -0.003(3) -0.004(3) 0.001(3) C14 0.043(4) 0.063(5) 0.033(4) 0.000(3) 0.004(3) -0.005(3) C13 0.051(5) 0.062(5) 0.040(4) -0.003(4) 0.003(3) -0.009(4) C12 0.064(5) 0.063(6) 0.045(5) 0.006(4) 0.007(4) -0.008(4) C11 0.041(4) 0.072(6) 0.039(4) 0.003(4) 0.006(3) 0.002(4) C10 0.061(5) 0.092(7) 0.039(5) 0.016(5) -0.001(4) 0.008(5) C9 0.046(5) 0.115(8) 0.033(4) 0.011(5) -0.002(3) 0.007(5) C8 0.056(5) 0.109(8) 0.028(4) -0.012(5) -0.006(3) -0.005(5) C7 0.054(5) 0.078(6) 0.036(4) -0.002(4) -0.004(3) -0.002(4) C6 0.040(4) 0.077(6) 0.029(4) -0.001(4) 0.004(3) 0.003(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 1.913(5) . ? Cu1 N2 1.937(6) . ? Cu1 N3 1.997(6) . ? Cu1 N1 2.066(7) . ? Cu1 N5 2.336(8) . ? N3 C15 1.140(9) . ? O1 C14 1.307(8) . ? N4 C15 1.291(9) . ? N4 C16 1.292(11) 1_655 ? N5 C16 1.143(10) . ? C16 N4 1.292(11) 1_455 ? N1 C2 1.470(10) . ? N1 C1 1.485(10) . ? N1 H1 0.81(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.518(11) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N2 1.452(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? N2 C4 1.287(9) . ? C4 C5 1.404(11) . ? C4 H4 0.9300 . ? C5 C14 1.425(10) . ? C5 C6 1.462(10) . ? C14 C13 1.419(11) . ? C13 C12 1.355(11) . ? C13 H13 0.9300 . ? C12 C11 1.428(11) . ? C12 H12 0.9300 . ? C11 C6 1.398(11) . ? C11 C10 1.424(10) . ? C10 C9 1.335(12) . ? C10 H10 0.9300 . ? C9 C8 1.387(13) . ? C9 H9 0.9300 . ? C8 C7 1.369(11) . ? C8 H8 0.9300 . ? C7 C6 1.420(11) . ? C7 H7 0.9300 . ? 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 N2 92.2(2) . . ? O1 Cu1 N3 92.3(2) . . ? N2 Cu1 N3 157.0(3) . . ? O1 Cu1 N1 174.6(2) . . ? N2 Cu1 N1 83.1(3) . . ? N3 Cu1 N1 91.0(3) . . ? O1 Cu1 N5 93.2(2) . . ? N2 Cu1 N5 98.7(3) . . ? N3 Cu1 N5 103.6(3) . . ? N1 Cu1 N5 90.2(3) . . ? C15 N3 Cu1 158.6(7) . . ? C14 O1 Cu1 127.3(5) . . ? C15 N4 C16 122.5(7) . 1_655 ? C16 N5 Cu1 164.6(7) . . ? N3 C15 N4 173.5(8) . . ? N5 C16 N4 173.7(8) . 1_455 ? C2 N1 C1 111.8(7) . . ? C2 N1 Cu1 106.2(5) . . ? C1 N1 Cu1 117.6(6) . . ? C2 N1 H1 110(4) . . ? C1 N1 H1 105(4) . . ? Cu1 N1 H1 106(4) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 107.8(6) . . ? N1 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? N1 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? N2 C3 C2 107.0(6) . . ? N2 C3 H3A 110.3 . . ? C2 C3 H3A 110.3 . . ? N2 C3 H3B 110.3 . . ? C2 C3 H3B 110.3 . . ? H3A C3 H3B 108.6 . . ? C4 N2 C3 119.9(6) . . ? C4 N2 Cu1 125.3(6) . . ? C3 N2 Cu1 114.8(5) . . ? N2 C4 C5 128.0(7) . . ? N2 C4 H4 116.0 . . ? C5 C4 H4 116.0 . . ? C4 C5 C14 121.2(6) . . ? C4 C5 C6 120.0(7) . . ? C14 C5 C6 118.8(7) . . ? O1 C14 C13 117.1(7) . . ? O1 C14 C5 124.3(7) . . ? C13 C14 C5 118.6(7) . . ? C12 C13 C14 122.2(7) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C13 C12 C11 121.1(8) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C6 C11 C10 120.7(8) . . ? C6 C11 C12 119.1(7) . . ? C10 C11 C12 120.1(8) . . ? C9 C10 C11 120.5(9) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C10 C9 C8 119.8(8) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C7 C8 C9 121.6(8) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C8 C7 C6 120.4(9) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C11 C6 C7 116.9(7) . . ? C11 C6 C5 120.1(7) . . ? C7 C6 C5 123.0(7) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.75 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.315 _refine_diff_density_min -0.783 _refine_diff_density_rms 0.130