# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dingshuai110428_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Cu N4 O3' _chemical_formula_weight 337.82 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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.5860(19) _cell_length_b 10.713(2) _cell_length_c 13.527(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1389.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.49044 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10202 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.27 _reflns_number_total 3428 _reflns_number_gt 3164 _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. Geometries of the disordered components were restrained to ideal values ; _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^)+(0.0443P)^2^+0.2756P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.015(11) _chemical_absolute_configuration syn _refine_ls_number_reflns 3428 _refine_ls_number_parameters 195 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0273 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0662 _refine_ls_wR_factor_gt 0.0640 _refine_ls_goodness_of_fit_ref 0.880 _refine_ls_restrained_S_all 0.909 _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 0.81046(2) 0.38026(2) 0.533823(18) 0.03155(8) Uani 1 1 d . . . O3 O 1.00465(15) 0.36728(14) 0.47200(11) 0.0364(3) Uani 1 1 d D . . H3 H 1.024(3) 0.2921(10) 0.4610(16) 0.055 Uiso 1 1 d D . . N1 N 0.79401(18) 0.51823(16) 0.44280(12) 0.0317(4) Uani 1 1 d . . . O2 O 0.61076(14) 0.36352(13) 0.54866(11) 0.0333(3) Uani 1 1 d . . . N2 N 0.84907(19) 0.24114(19) 0.62162(15) 0.0396(4) Uani 1 1 d . . . O1 O 0.35909(16) 0.33503(16) 0.62127(13) 0.0439(4) Uani 1 1 d . . . C2 C 0.9302(2) 0.5576(2) 0.40051(18) 0.0376(5) Uani 1 1 d . . . H2 H 0.9801 0.6045 0.4517 0.045 Uiso 1 1 calc R . . C1 C 0.5470(2) 0.55475(19) 0.46651(18) 0.0350(4) Uani 1 1 d . . . C3 C 0.6825(2) 0.5790(2) 0.42436(16) 0.0364(4) Uani 1 1 d . . . H3A H 0.6893 0.6447 0.3798 0.044 Uiso 1 1 calc R . . C4 C 0.8874(2) 0.1842(2) 0.68653(18) 0.0375(5) Uani 1 1 d . . . C5 C 0.3803(2) 0.4397(2) 0.56596(16) 0.0342(4) Uani 1 1 d . . . C6 C 0.2793(2) 0.5270(2) 0.54405(19) 0.0423(5) Uani 1 1 d . . . H6 H 0.1903 0.5184 0.5705 0.051 Uiso 1 1 calc R . . C7 C 0.51923(19) 0.45133(17) 0.52727(15) 0.0295(4) Uani 1 1 d . . . C8 C 0.4397(3) 0.6417(2) 0.4441(2) 0.0471(6) Uani 1 1 d . . . H8 H 0.4592 0.7086 0.4026 0.057 Uiso 1 1 calc R . . N4 N 1.1165(3) 0.0247(3) 0.83313(19) 0.0640(7) Uani 1 1 d . . . C10 C 0.3094(3) 0.6292(2) 0.4819(2) 0.0486(6) Uani 1 1 d . . . H10 H 0.2407 0.6875 0.4671 0.058 Uiso 1 1 calc R . . C11 C 1.0277(3) 0.0712(2) 0.79438(18) 0.0459(6) Uani 1 1 d . . . C12 C 0.9220(3) 0.6395(3) 0.3095(2) 0.0649(9) Uani 1 1 d . . . H12A H 0.8680 0.5982 0.2595 0.097 Uiso 1 1 calc R . . H12B H 1.0144 0.6550 0.2849 0.097 Uiso 1 1 calc R . . H12C H 0.8785 0.7174 0.3262 0.097 Uiso 1 1 calc R . . N3 N 0.9119(3) 0.1242(4) 0.7658(2) 0.0893(10) Uani 1 1 d U . . C15 C 1.0107(2) 0.4376(2) 0.38186(18) 0.0416(5) Uani 1 1 d D . . H15A H 0.9687 0.3909 0.3281 0.050 Uiso 1 1 calc R . . H15B H 1.1068 0.4561 0.3647 0.050 Uiso 1 1 calc R . . C16 C 0.2313(3) 0.3229(3) 0.6733(2) 0.0545(7) Uani 1 1 d . . . H16A H 0.1553 0.3214 0.6270 0.082 Uiso 1 1 calc R . . H16B H 0.2201 0.3925 0.7173 0.082 Uiso 1 1 calc R . . H16C H 0.2319 0.2468 0.7106 0.082 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 0.02195(11) 0.03552(12) 0.03718(13) 0.00935(11) -0.00090(10) -0.00018(11) O3 0.0294(7) 0.0353(7) 0.0445(8) 0.0057(8) 0.0050(6) 0.0032(6) N1 0.0261(8) 0.0339(8) 0.0352(9) 0.0046(6) -0.0010(7) -0.0026(7) O2 0.0220(6) 0.0334(7) 0.0445(8) 0.0085(6) -0.0002(5) -0.0003(5) N2 0.0347(9) 0.0426(10) 0.0415(11) 0.0093(9) 0.0020(8) 0.0060(8) O1 0.0292(7) 0.0512(9) 0.0514(10) 0.0104(8) 0.0095(7) 0.0041(7) C2 0.0304(10) 0.0393(11) 0.0429(12) 0.0086(10) 0.0046(9) -0.0025(9) C1 0.0275(9) 0.0338(10) 0.0437(11) 0.0016(10) -0.0024(9) 0.0029(7) C3 0.0348(10) 0.0329(10) 0.0416(11) 0.0089(8) -0.0027(9) -0.0028(9) C4 0.0316(10) 0.0397(12) 0.0413(12) 0.0064(10) 0.0060(9) -0.0002(9) C5 0.0268(10) 0.0380(11) 0.0378(11) -0.0041(8) -0.0009(8) 0.0012(8) C6 0.0275(10) 0.0479(12) 0.0514(13) -0.0079(11) 0.0011(9) 0.0065(8) C7 0.0249(8) 0.0322(9) 0.0314(10) -0.0030(8) -0.0023(8) -0.0007(7) C8 0.0397(11) 0.0360(12) 0.0657(16) 0.0080(10) -0.0037(11) 0.0047(9) N4 0.0757(17) 0.0615(15) 0.0548(15) 0.0116(12) -0.0132(13) 0.0132(14) C10 0.0353(10) 0.0401(12) 0.0704(17) -0.0015(11) -0.0061(12) 0.0136(11) C11 0.0616(16) 0.0424(12) 0.0339(11) 0.0116(9) -0.0004(11) 0.0026(11) C12 0.0523(15) 0.074(2) 0.0679(18) 0.0355(16) 0.0176(14) 0.0031(14) N3 0.0685(16) 0.128(2) 0.0717(17) 0.0552(18) 0.0123(13) 0.0191(18) C15 0.0359(11) 0.0452(12) 0.0436(12) 0.0059(10) 0.0100(10) -0.0002(10) C16 0.0345(12) 0.0723(18) 0.0566(16) 0.0121(14) 0.0116(11) -0.0004(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.9302(17) . ? Cu1 O2 1.9332(14) . ? Cu1 N2 1.9413(19) . ? Cu1 O3 2.0454(15) . ? Cu1 N4 2.474(2) 4_756 ? O3 C15 1.434(3) . ? N1 C3 1.276(3) . ? N1 C2 1.486(3) . ? O2 C7 1.318(2) . ? N2 C4 1.131(3) . ? O1 C5 1.363(3) . ? O1 C16 1.419(3) . ? C2 C12 1.514(3) . ? C2 C15 1.521(3) . ? C1 C7 1.405(3) . ? C1 C8 1.421(3) . ? C1 C3 1.442(3) . ? C4 N3 1.272(3) . ? C5 C6 1.378(3) . ? C5 C7 1.436(3) . ? C6 C10 1.410(4) . ? C8 C10 1.356(3) . ? N4 C11 1.118(3) . ? N4 Cu1 2.474(2) 4_746 ? C11 N3 1.305(4) . ? 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 O2 93.23(7) . . ? N1 Cu1 N2 173.57(8) . . ? O2 Cu1 N2 93.10(7) . . ? N1 Cu1 O3 82.27(7) . . ? O2 Cu1 O3 159.61(7) . . ? N2 Cu1 O3 91.40(7) . . ? N1 Cu1 N4 90.48(8) . 4_756 ? O2 Cu1 N4 105.23(8) . 4_756 ? N2 Cu1 N4 88.92(9) . 4_756 ? O3 Cu1 N4 94.73(8) . 4_756 ? C15 O3 Cu1 110.41(12) . . ? C3 N1 C2 121.03(17) . . ? C3 N1 Cu1 125.71(15) . . ? C2 N1 Cu1 113.03(13) . . ? C7 O2 Cu1 124.75(12) . . ? C4 N2 Cu1 162.1(2) . . ? C5 O1 C16 118.41(19) . . ? N1 C2 C12 115.6(2) . . ? N1 C2 C15 105.64(18) . . ? C12 C2 C15 112.4(2) . . ? C7 C1 C8 120.3(2) . . ? C7 C1 C3 122.94(18) . . ? C8 C1 C3 116.8(2) . . ? N1 C3 C1 125.84(19) . . ? N2 C4 N3 170.9(3) . . ? O1 C5 C6 124.8(2) . . ? O1 C5 C7 114.17(18) . . ? C6 C5 C7 121.0(2) . . ? C5 C6 C10 120.7(2) . . ? O2 C7 C1 124.39(18) . . ? O2 C7 C5 118.38(18) . . ? C1 C7 C5 117.21(18) . . ? C10 C8 C1 121.4(2) . . ? C11 N4 Cu1 146.7(3) . 4_746 ? C8 C10 C6 119.4(2) . . ? N4 C11 N3 168.8(3) . . ? C4 N3 C11 128.8(3) . . ? O3 C15 C2 106.40(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.417 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.045 _database_code_depnum_ccdc_archive 'CCDC 926233' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dingshuai110317_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 Cu N4 O3' _chemical_formula_weight 337.82 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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5890(19) _cell_length_b 10.709(2) _cell_length_c 13.528(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1389.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 _exptl_absorpt_coefficient_mu 1.588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.49044 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10187 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0325 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3422 _reflns_number_gt 3204 _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^)+(0.0344P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.015(10) _chemical_absolute_configuration syn _refine_ls_number_reflns 3422 _refine_ls_number_parameters 195 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0235 _refine_ls_wR_factor_ref 0.0635 _refine_ls_wR_factor_gt 0.0627 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.061 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2316(2) 0.6771(3) 0.1731(2) 0.0534(6) Uani 1 1 d . . . H1A H 0.1557 0.6785 0.1269 0.080 Uiso 1 1 calc R . . H1B H 0.2322 0.7535 0.2103 0.080 Uiso 1 1 calc R . . H1C H 0.2205 0.6077 0.2174 0.080 Uiso 1 1 calc R . . C2 C 0.3804(2) 0.5602(2) 0.06601(15) 0.0343(4) Uani 1 1 d . . . C3 C 0.2793(2) 0.4733(2) 0.04435(18) 0.0412(5) Uani 1 1 d . . . H3 H 0.1904 0.4819 0.0709 0.049 Uiso 1 1 calc R . . C4 C 0.3096(2) 0.3709(2) -0.01808(18) 0.0482(5) Uani 1 1 d . . . H4 H 0.2408 0.3126 -0.0331 0.058 Uiso 1 1 calc R . . C5 C 0.4400(2) 0.3583(2) -0.05592(19) 0.0465(5) Uani 1 1 d . . . H5 H 0.4596 0.2914 -0.0975 0.056 Uiso 1 1 calc R . . C6 C 0.51923(19) 0.54880(16) 0.02718(14) 0.0294(4) Uani 1 1 d . . . C7 C 0.5469(2) 0.44535(18) -0.03330(17) 0.0351(4) Uani 1 1 d . . . C8 C 0.6825(2) 0.42142(18) -0.07572(15) 0.0358(4) Uani 1 1 d . . . H8 H 0.6889 0.3560 -0.1207 0.043 Uiso 1 1 calc R . . C9 C 0.9301(2) 0.4424(2) -0.09946(16) 0.0375(4) Uani 1 1 d . . . H9 H 0.9799 0.3952 -0.0484 0.045 Uiso 1 1 calc R . . C10 C 0.9215(3) 0.3608(3) -0.1908(2) 0.0633(8) Uani 1 1 d . . . H10A H 0.8793 0.2823 -0.1739 0.095 Uiso 1 1 calc R . . H10B H 1.0137 0.3464 -0.2161 0.095 Uiso 1 1 calc R . . H10C H 0.8663 0.4018 -0.2402 0.095 Uiso 1 1 calc R . . C11 C 1.0106(2) 0.5621(2) -0.11817(16) 0.0406(5) Uani 1 1 d D . . H11A H 1.1066 0.5434 -0.1354 0.049 Uiso 1 1 calc R . . H11B H 0.9687 0.6088 -0.1719 0.049 Uiso 1 1 calc R . . C13 C 0.8877(2) 0.8161(2) 0.18640(17) 0.0365(5) Uani 1 1 d . . . C15 C 1.0276(3) 0.9285(2) 0.29444(16) 0.0449(5) Uani 1 1 d . . . H3A H 1.021(3) 0.7085(10) -0.0410(16) 0.067 Uiso 1 1 d D . . N1 N 0.79403(17) 0.48165(15) -0.05732(11) 0.0311(3) Uani 1 1 d . . . N2 N 0.84925(19) 0.75896(18) 0.12152(14) 0.0385(4) Uani 1 1 d . . . N3 N 0.9120(3) 0.8754(3) 0.26591(19) 0.0885(9) Uani 1 1 d U . . N4 N 1.1163(3) 0.9755(2) 0.33321(17) 0.0632(6) Uani 1 1 d . . . O1 O 0.35908(15) 0.66491(15) 0.12126(12) 0.0440(4) Uani 1 1 d . . . O2 O 0.61067(13) 0.63650(13) 0.04858(10) 0.0325(3) Uani 1 1 d . . . O3 O 1.00485(14) 0.63263(13) -0.02803(10) 0.0361(3) Uani 1 1 d D . . Cu1 Cu 0.81054(2) 0.61973(2) 0.033828(17) 0.03112(7) 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 C1 0.0323(12) 0.0720(17) 0.0558(14) -0.0135(13) 0.0108(10) -0.0002(11) C2 0.0279(10) 0.0378(10) 0.0372(10) 0.0049(8) -0.0010(8) -0.0007(8) C3 0.0251(10) 0.0461(11) 0.0522(12) 0.0072(10) 0.0014(9) -0.0052(8) C4 0.0358(11) 0.0396(11) 0.0690(15) 0.0031(11) -0.0064(11) -0.0133(11) C5 0.0393(11) 0.0360(11) 0.0642(14) -0.0086(10) -0.0038(10) -0.0046(9) C6 0.0250(8) 0.0315(9) 0.0316(9) 0.0026(8) -0.0032(8) 0.0005(7) C7 0.0292(9) 0.0333(9) 0.0428(10) -0.0017(9) -0.0027(9) -0.0027(7) C8 0.0344(10) 0.0317(9) 0.0412(10) -0.0095(8) -0.0021(9) 0.0029(8) C9 0.0298(10) 0.0406(11) 0.0422(11) -0.0086(9) 0.0034(9) 0.0020(8) C10 0.0517(15) 0.0710(19) 0.0672(16) -0.0341(15) 0.0168(13) -0.0029(13) C11 0.0341(11) 0.0440(11) 0.0437(11) -0.0050(10) 0.0093(9) 0.0017(9) C13 0.0297(10) 0.0386(11) 0.0412(11) -0.0063(9) 0.0047(9) 0.0009(8) C15 0.0595(15) 0.0417(11) 0.0335(10) -0.0114(9) -0.0012(10) -0.0021(11) N1 0.0260(8) 0.0326(8) 0.0346(8) -0.0049(6) -0.0008(6) 0.0030(7) N2 0.0345(9) 0.0412(9) 0.0398(10) -0.0095(8) 0.0017(7) -0.0061(7) N3 0.0675(16) 0.125(2) 0.0729(15) -0.0564(18) 0.0119(13) -0.0191(17) N4 0.0726(16) 0.0623(14) 0.0547(13) -0.0097(11) -0.0140(12) -0.0121(13) O1 0.0284(7) 0.0518(9) 0.0517(9) -0.0105(8) 0.0089(6) -0.0037(7) O2 0.0212(6) 0.0329(7) 0.0433(7) -0.0076(6) -0.0001(5) 0.0003(5) O3 0.0295(6) 0.0345(7) 0.0444(7) -0.0057(7) 0.0056(6) -0.0038(6) Cu1 0.02154(10) 0.03519(12) 0.03662(12) -0.00906(11) -0.00082(10) 0.00010(10) _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 C1 O1 1.416(3) . ? C2 O1 1.363(3) . ? C2 C3 1.376(3) . ? C2 C6 1.436(3) . ? C3 C4 1.414(3) . ? C4 C5 1.358(3) . ? C5 C7 1.419(3) . ? C6 O2 1.317(2) . ? C6 C7 1.403(3) . ? C7 C8 1.444(3) . ? C8 N1 1.274(3) . ? C9 N1 1.484(2) . ? C9 C10 1.516(3) . ? C9 C11 1.518(3) . ? C11 O3 1.436(2) . ? C13 N2 1.132(3) . ? C13 N3 1.271(3) . ? C15 N4 1.119(3) . ? C15 N3 1.304(3) . ? N1 Cu1 1.9319(16) . ? N2 Cu1 1.9412(18) . ? N4 Cu1 2.473(2) 3_755 ? O2 Cu1 1.9352(13) . ? O3 Cu1 2.0472(14) . ? Cu1 N4 2.473(2) 3_745 ? 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 C2 C3 124.58(19) . . ? O1 C2 C6 114.17(17) . . ? C3 C2 C6 121.2(2) . . ? C2 C3 C4 120.5(2) . . ? C5 C4 C3 119.4(2) . . ? C4 C5 C7 121.3(2) . . ? O2 C6 C7 124.44(17) . . ? O2 C6 C2 118.43(17) . . ? C7 C6 C2 117.11(17) . . ? C6 C7 C5 120.52(19) . . ? C6 C7 C8 122.85(18) . . ? C5 C7 C8 116.63(19) . . ? N1 C8 C7 126.06(18) . . ? N1 C9 C10 115.42(19) . . ? N1 C9 C11 105.78(17) . . ? C10 C9 C11 112.23(19) . . ? O3 C11 C9 106.44(16) . . ? N2 C13 N3 170.6(3) . . ? N4 C15 N3 168.8(3) . . ? C8 N1 C9 121.30(16) . . ? C8 N1 Cu1 125.53(14) . . ? C9 N1 Cu1 112.96(13) . . ? C13 N2 Cu1 162.07(19) . . ? C13 N3 C15 128.6(3) . . ? C15 N4 Cu1 146.9(2) . 3_755 ? C2 O1 C1 118.53(18) . . ? C6 O2 Cu1 124.78(12) . . ? C11 O3 Cu1 110.30(12) . . ? N1 Cu1 O2 93.19(6) . . ? N1 Cu1 N2 173.54(7) . . ? O2 Cu1 N2 93.16(7) . . ? N1 Cu1 O3 82.26(6) . . ? O2 Cu1 O3 159.60(6) . . ? N2 Cu1 O3 91.37(7) . . ? N1 Cu1 N4 90.54(8) . 3_745 ? O2 Cu1 N4 105.31(8) . 3_745 ? N2 Cu1 N4 88.90(9) . 3_745 ? O3 Cu1 N4 94.65(8) . 3_745 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 176.6(2) . . . . ? C6 C2 C3 C4 -0.8(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C3 C4 C5 C7 0.6(4) . . . . ? O1 C2 C6 O2 0.8(3) . . . . ? C3 C2 C6 O2 178.40(19) . . . . ? O1 C2 C6 C7 -177.79(17) . . . . ? C3 C2 C6 C7 -0.2(3) . . . . ? O2 C6 C7 C5 -177.2(2) . . . . ? C2 C6 C7 C5 1.3(3) . . . . ? O2 C6 C7 C8 2.6(3) . . . . ? C2 C6 C7 C8 -178.88(18) . . . . ? C4 C5 C7 C6 -1.6(4) . . . . ? C4 C5 C7 C8 178.6(2) . . . . ? C6 C7 C8 N1 6.9(3) . . . . ? C5 C7 C8 N1 -173.3(2) . . . . ? N1 C9 C11 O3 50.6(2) . . . . ? C10 C9 C11 O3 177.24(19) . . . . ? C7 C8 N1 C9 175.14(19) . . . . ? C7 C8 N1 Cu1 0.8(3) . . . . ? C10 C9 N1 C8 21.2(3) . . . . ? C11 C9 N1 C8 145.9(2) . . . . ? C10 C9 N1 Cu1 -163.81(17) . . . . ? C11 C9 N1 Cu1 -39.1(2) . . . . ? N3 C13 N2 Cu1 -87.5(19) . . . . ? N2 C13 N3 C15 171.2(15) . . . . ? N4 C15 N3 C13 -168.7(14) . . . . ? N3 C15 N4 Cu1 -28.4(19) . . . 3_755 ? C3 C2 O1 C1 10.4(3) . . . . ? C6 C2 O1 C1 -172.10(19) . . . . ? C7 C6 O2 Cu1 -18.2(3) . . . . ? C2 C6 O2 Cu1 163.31(13) . . . . ? C9 C11 O3 Cu1 -40.24(19) . . . . ? C8 N1 Cu1 O2 -11.22(18) . . . . ? C9 N1 Cu1 O2 174.06(14) . . . . ? C8 N1 Cu1 N2 179(25) . . . . ? C9 N1 Cu1 N2 4.5(8) . . . . ? C8 N1 Cu1 O3 -171.23(18) . . . . ? C9 N1 Cu1 O3 14.04(14) . . . . ? C8 N1 Cu1 N4 94.15(18) . . . 3_745 ? C9 N1 Cu1 N4 -80.58(15) . . . 3_745 ? C6 O2 Cu1 N1 19.62(16) . . . . ? C6 O2 Cu1 N2 -161.55(16) . . . . ? C6 O2 Cu1 O3 95.9(2) . . . . ? C6 O2 Cu1 N4 -71.82(16) . . . 3_745 ? C13 N2 Cu1 N1 -73.2(10) . . . . ? C13 N2 Cu1 O2 117.2(6) . . . . ? C13 N2 Cu1 O3 -82.7(6) . . . . ? C13 N2 Cu1 N4 11.9(6) . . . 3_745 ? C11 O3 Cu1 N1 15.60(13) . . . . ? C11 O3 Cu1 O2 -62.6(2) . . . . ? C11 O3 Cu1 N2 -165.47(13) . . . . ? C11 O3 Cu1 N4 105.52(13) . . . 3_745 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.456 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.044 _database_code_depnum_ccdc_archive 'CCDC 926234' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_shelx _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 Cu N4 O3' _chemical_formula_weight 323.80 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 Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5958(19) _cell_length_b 10.990(2) _cell_length_c 12.258(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1292.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 1.702 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.49044 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos, Gemini' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 13542 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_sigmaI/netI 0.0624 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 27.86 _reflns_number_total 3082 _reflns_number_gt 2486 _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^)+(0.0139P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(18) _refine_ls_number_reflns 3082 _refine_ls_number_parameters 185 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0238 _refine_ls_wR_factor_ref 0.0525 _refine_ls_wR_factor_gt 0.0518 _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_restrained_S_all 0.962 _refine_ls_shift/su_max 0.005 _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 C1 C 0.2577(2) 0.3355(2) 0.1847(2) 0.0238(6) Uani 1 1 d . . . H1A H 0.1839 0.3378 0.1319 0.036 Uiso 1 1 calc R . . H1B H 0.2469 0.4019 0.2349 0.036 Uiso 1 1 calc R . . H1C H 0.2540 0.2599 0.2238 0.036 Uiso 1 1 calc R . . C2 C 0.4132(2) 0.4482(2) 0.0686(2) 0.0166(6) Uani 1 1 d . . . C3 C 0.3163(3) 0.5395(2) 0.05258(19) 0.0236(6) Uani 1 1 d . . . H3 H 0.2289 0.5339 0.0850 0.028 Uiso 1 1 calc R . . C4 C 0.3490(3) 0.6399(2) -0.01197(19) 0.0246(6) Uani 1 1 d . . . H4 H 0.2837 0.7013 -0.0225 0.029 Uiso 1 1 calc R . . C5 C 0.4777(3) 0.6479(2) -0.0600(2) 0.0232(6) Uani 1 1 d . . . H5 H 0.4992 0.7152 -0.1028 0.028 Uiso 1 1 calc R . . C6 C 0.5780(2) 0.5556(2) -0.04527(19) 0.0173(6) Uani 1 1 d . . . C7 C 0.5470(2) 0.4538(2) 0.0205(2) 0.0146(5) Uani 1 1 d . . . C8 C 0.7098(3) 0.5697(2) -0.10035(18) 0.0180(6) Uani 1 1 d . . . H8 H 0.7172 0.6340 -0.1493 0.022 Uiso 1 1 calc R . . C9 C 0.9474(2) 0.5323(2) -0.1447(2) 0.0232(7) Uani 1 1 d . . . H9A H 0.9976 0.5948 -0.1050 0.028 Uiso 1 1 calc R . . H9B H 0.9279 0.5622 -0.2176 0.028 Uiso 1 1 calc R . . C10 C 1.0343(3) 0.4159(2) -0.1506(2) 0.0230(6) Uani 1 1 d D . . H10A H 0.9946 0.3594 -0.2029 0.028 Uiso 1 1 calc R . . H10B H 1.1293 0.4341 -0.1721 0.028 Uiso 1 1 calc R . . C11 C 0.9031(2) 0.1775(2) 0.1857(2) 0.0161(6) Uani 1 1 d . . . C12 C 1.0422(3) 0.0636(2) 0.3013(2) 0.0210(6) Uani 1 1 d . . . N1 N 0.8174(2) 0.50263(17) -0.08856(15) 0.0152(4) Uani 1 1 d . . . N2 N 0.87111(19) 0.24900(17) 0.12304(17) 0.0185(5) Uani 1 1 d . . . N3 N 0.9217(2) 0.0954(2) 0.25908(18) 0.0305(6) Uani 1 1 d . . . N4 N 1.1397(2) 0.02875(19) 0.34532(17) 0.0312(6) Uani 1 1 d . . . O1 O 0.38960(16) 0.34580(15) 0.13017(13) 0.0221(5) Uani 1 1 d . . . O2 O 0.63391(14) 0.36124(13) 0.03682(12) 0.0153(4) Uani 1 1 d . . . O3 O 1.03051(16) 0.36558(14) -0.04245(13) 0.0176(4) Uani 1 1 d D . . H3A H 1.055(2) 0.2949(10) -0.0384(16) 0.026 Uiso 1 1 d D . . Cu1 Cu 0.83362(3) 0.37728(3) 0.01982(2) 0.01432(8) 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 C1 0.0180(14) 0.0252(15) 0.0283(15) -0.0001(12) 0.0066(12) -0.0029(11) C2 0.0183(14) 0.0168(15) 0.0146(13) -0.0033(12) -0.0019(10) 0.0007(11) C3 0.0187(14) 0.0304(15) 0.0217(14) -0.0016(12) 0.0008(11) 0.0071(12) C4 0.0237(14) 0.0204(14) 0.0296(14) -0.0013(14) 0.0008(12) 0.0151(12) C5 0.0314(15) 0.0154(15) 0.0226(14) 0.0046(11) -0.0014(11) 0.0044(12) C6 0.0160(13) 0.0190(14) 0.0170(15) -0.0003(11) -0.0007(10) 0.0032(10) C7 0.0147(12) 0.0157(13) 0.0133(12) -0.0029(12) -0.0035(11) -0.0013(10) C8 0.0275(15) 0.0125(14) 0.0141(13) 0.0045(11) -0.0013(10) -0.0039(11) C9 0.0201(15) 0.0232(16) 0.0264(16) 0.0102(13) 0.0039(12) -0.0001(12) C10 0.0221(14) 0.0209(15) 0.0262(15) 0.0079(12) 0.0101(11) 0.0006(11) C11 0.0120(13) 0.0179(14) 0.0184(14) -0.0014(12) 0.0044(11) -0.0038(11) C12 0.0366(17) 0.0131(14) 0.0133(14) 0.0035(12) 0.0058(12) 0.0019(12) N1 0.0148(11) 0.0143(11) 0.0164(10) 0.0006(9) 0.0006(9) 0.0007(9) N2 0.0145(12) 0.0213(13) 0.0196(12) 0.0036(10) 0.0016(9) 0.0023(9) N3 0.0257(13) 0.0347(16) 0.0311(14) 0.0179(12) 0.0021(10) -0.0027(11) N4 0.0444(18) 0.0279(14) 0.0214(12) 0.0026(11) -0.0055(12) 0.0156(13) O1 0.0149(9) 0.0262(12) 0.0252(11) 0.0041(9) 0.0062(7) 0.0022(8) O2 0.0106(8) 0.0105(9) 0.0248(9) 0.0018(8) -0.0016(6) 0.0010(6) O3 0.0157(8) 0.0124(9) 0.0246(10) 0.0040(9) 0.0015(7) 0.0037(8) Cu1 0.01231(13) 0.01549(15) 0.01515(13) 0.00236(16) -0.00127(12) -0.00040(14) _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 C1 O1 1.436(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O1 1.374(3) . ? C2 C3 1.383(3) . ? C2 C7 1.414(3) . ? C3 C4 1.393(3) . ? C3 H3 0.9300 . ? C4 C5 1.371(3) . ? C4 H4 0.9300 . ? C5 C6 1.410(3) . ? C5 H5 0.9300 . ? C6 C7 1.410(3) . ? C6 C8 1.442(3) . ? C7 O2 1.330(2) . ? C8 N1 1.276(3) . ? C8 H8 0.9300 . ? C9 N1 1.462(3) . ? C9 C10 1.529(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 O3 1.437(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.141(3) . ? C11 N3 1.287(3) . ? C12 N4 1.146(3) . ? C12 N3 1.314(3) . ? N1 Cu1 1.9202(18) . ? N2 Cu1 1.9281(19) . ? N4 Cu1 2.360(2) 3_745 ? O2 Cu1 1.9357(14) . ? O3 Cu1 2.0417(16) . ? O3 H3A 0.813(9) . ? Cu1 N4 2.360(2) 3_755 ? 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 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 124.2(2) . . ? O1 C2 C7 114.5(2) . . ? C3 C2 C7 121.3(2) . . ? C2 C3 C4 120.2(2) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 120.9(2) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C7 C6 C5 120.0(2) . . ? C7 C6 C8 122.5(2) . . ? C5 C6 C8 117.5(2) . . ? O2 C7 C6 124.1(2) . . ? O2 C7 C2 118.2(2) . . ? C6 C7 C2 117.7(2) . . ? N1 C8 C6 126.5(2) . . ? N1 C8 H8 116.8 . . ? C6 C8 H8 116.8 . . ? N1 C9 C10 107.5(2) . . ? N1 C9 H9A 110.2 . . ? C10 C9 H9A 110.2 . . ? N1 C9 H9B 110.2 . . ? C10 C9 H9B 110.2 . . ? H9A C9 H9B 108.5 . . ? O3 C10 C9 105.33(19) . . ? O3 C10 H10A 110.7 . . ? C9 C10 H10A 110.7 . . ? O3 C10 H10B 110.7 . . ? C9 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? N2 C11 N3 172.3(3) . . ? N4 C12 N3 173.1(3) . . ? C8 N1 C9 120.5(2) . . ? C8 N1 Cu1 123.94(17) . . ? C9 N1 Cu1 114.61(16) . . ? C11 N2 Cu1 174.6(2) . . ? C11 N3 C12 125.7(2) . . ? C12 N4 Cu1 130.8(2) . 3_745 ? C2 O1 C1 117.78(18) . . ? C7 O2 Cu1 122.30(14) . . ? C10 O3 Cu1 110.13(13) . . ? C10 O3 H3A 114.7(15) . . ? Cu1 O3 H3A 107.6(16) . . ? N1 Cu1 N2 173.58(9) . . ? N1 Cu1 O2 93.40(7) . . ? N2 Cu1 O2 92.72(7) . . ? N1 Cu1 O3 82.05(7) . . ? N2 Cu1 O3 91.53(7) . . ? O2 Cu1 O3 161.92(6) . . ? N1 Cu1 N4 89.28(8) . 3_755 ? N2 Cu1 N4 92.05(8) . 3_755 ? O2 Cu1 N4 95.51(7) . 3_755 ? O3 Cu1 N4 101.89(7) . 3_755 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 -179.5(2) . . . . ? C7 C2 C3 C4 0.0(4) . . . . ? C2 C3 C4 C5 0.2(4) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C4 C5 C6 C7 -0.7(4) . . . . ? C4 C5 C6 C8 178.8(2) . . . . ? C5 C6 C7 O2 178.4(2) . . . . ? C8 C6 C7 O2 -1.0(4) . . . . ? C5 C6 C7 C2 0.8(3) . . . . ? C8 C6 C7 C2 -178.6(2) . . . . ? O1 C2 C7 O2 1.3(3) . . . . ? C3 C2 C7 O2 -178.2(2) . . . . ? O1 C2 C7 C6 179.1(2) . . . . ? C3 C2 C7 C6 -0.5(4) . . . . ? C7 C6 C8 N1 -8.0(4) . . . . ? C5 C6 C8 N1 172.6(2) . . . . ? N1 C9 C10 O3 -47.5(3) . . . . ? C6 C8 N1 C9 -176.1(2) . . . . ? C6 C8 N1 Cu1 -7.6(4) . . . . ? C10 C9 N1 C8 -158.8(2) . . . . ? C10 C9 N1 Cu1 31.7(2) . . . . ? N3 C11 N2 Cu1 149.7(16) . . . . ? N2 C11 N3 C12 -170(2) . . . . ? N4 C12 N3 C11 173(2) . . . . ? N3 C12 N4 Cu1 8(3) . . . 3_745 ? C3 C2 O1 C1 -2.6(3) . . . . ? C7 C2 O1 C1 177.9(2) . . . . ? C6 C7 O2 Cu1 23.5(3) . . . . ? C2 C7 O2 Cu1 -158.93(16) . . . . ? C9 C10 O3 Cu1 42.6(2) . . . . ? C8 N1 Cu1 N2 -175.7(6) . . . . ? C9 N1 Cu1 N2 -6.6(8) . . . . ? C8 N1 Cu1 O2 21.8(2) . . . . ? C9 N1 Cu1 O2 -169.12(16) . . . . ? C8 N1 Cu1 O3 -175.8(2) . . . . ? C9 N1 Cu1 O3 -6.72(16) . . . . ? C8 N1 Cu1 N4 -73.7(2) . . . 3_755 ? C9 N1 Cu1 N4 95.40(17) . . . 3_755 ? C11 N2 Cu1 N1 45(3) . . . . ? C11 N2 Cu1 O2 -153(2) . . . . ? C11 N2 Cu1 O3 45(2) . . . . ? C11 N2 Cu1 N4 -57(2) . . . 3_755 ? C7 O2 Cu1 N1 -29.36(17) . . . . ? C7 O2 Cu1 N2 152.57(17) . . . . ? C7 O2 Cu1 O3 -104.0(2) . . . . ? C7 O2 Cu1 N4 60.24(17) . . . 3_755 ? C10 O3 Cu1 N1 -21.58(14) . . . . ? C10 O3 Cu1 N2 158.43(15) . . . . ? C10 O3 Cu1 O2 54.9(3) . . . . ? C10 O3 Cu1 N4 -109.15(15) . . . 3_755 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.593 _refine_diff_density_min -0.369 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 926235' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dingshuai110927_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 Br2 Cu2 N8 O4' _chemical_formula_weight 773.40 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' Br Br -0.2901 2.4595 '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 8.2239(16) _cell_length_b 9.5128(19) _cell_length_c 10.460(2) _cell_angle_alpha 64.03(3) _cell_angle_beta 71.43(3) _cell_angle_gamma 83.95(3) _cell_volume 696.8(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.843 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 382 _exptl_absorpt_coefficient_mu 4.440 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.49044 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 5161 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0383 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.38 _reflns_number_total 3445 _reflns_number_gt 2929 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+5.8660P] 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 3445 _refine_ls_number_parameters 184 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0843 _refine_ls_R_factor_gt 0.0759 _refine_ls_wR_factor_ref 0.1973 _refine_ls_wR_factor_gt 0.1943 _refine_ls_goodness_of_fit_ref 1.266 _refine_ls_restrained_S_all 1.282 _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 C1 C 1.0886(10) 0.7924(8) -0.0836(9) 0.0350(15) Uani 1 1 d . . . C2 C 1.2396(10) 0.8832(9) -0.1807(9) 0.0426(18) Uani 1 1 d . . . H2 H 1.3444 0.8349 -0.1861 0.051 Uiso 1 1 calc R . . C3 C 1.2377(11) 1.0423(10) -0.2687(10) 0.049(2) Uani 1 1 d . . . H3 H 1.3397 1.0995 -0.3318 0.058 Uiso 1 1 calc R . . C4 C 1.0841(11) 1.1145(8) -0.2617(9) 0.0381(16) Uani 1 1 d . . . C5 C 0.9351(10) 1.0328(9) -0.1677(9) 0.0379(16) Uani 1 1 d . . . H5 H 0.8324 1.0845 -0.1643 0.046 Uiso 1 1 calc R . . C6 C 0.9320(9) 0.8730(8) -0.0758(8) 0.0323(15) Uani 1 1 d . . . C7 C 0.7681(10) 0.7959(9) 0.0190(9) 0.0402(17) Uani 1 1 d . . . H7 H 0.6717 0.8562 0.0137 0.048 Uiso 1 1 calc R . . C8 C 0.5665(14) 0.5849(14) 0.1985(13) 0.068(3) Uani 1 1 d U . . H8A H 0.5704 0.5287 0.1406 0.082 Uiso 1 1 d R . . C9 C 0.5694(15) 0.4424(14) 0.3280(14) 0.075(3) Uani 1 1 d DU . . H9A H 0.4963 0.3640 0.3372 0.090 Uiso 1 1 d R . . H9B H 0.5214 0.4639 0.4138 0.090 Uiso 1 1 d R . . C10 C 0.4226(17) 0.6588(18) 0.1687(19) 0.105(5) Uani 1 1 d U . . H10A H 0.3227 0.5944 0.2399 0.158 Uiso 1 1 d R . . H10B H 0.4179 0.7567 0.1754 0.158 Uiso 1 1 d R . . H10C H 0.4260 0.6776 0.0699 0.158 Uiso 1 1 d R . . C11 C 1.1793(11) 0.2632(9) 0.2770(10) 0.0429(18) Uani 1 1 d . . . C12 C 1.2898(11) 0.0257(12) 0.3809(11) 0.058(3) Uani 1 1 d . . . N1 N 0.7435(8) 0.6503(8) 0.1107(7) 0.0381(14) Uani 1 1 d . . . N2 N 1.0839(10) 0.3600(8) 0.2414(8) 0.0449(16) Uani 1 1 d . . . N3 N 1.3034(11) 0.1767(10) 0.3097(13) 0.077(3) Uani 1 1 d . . . N4 N 1.2951(13) -0.1060(10) 0.4406(12) 0.082(3) Uani 1 1 d . . . O1 O 1.1003(7) 0.6394(6) -0.0093(6) 0.0426(13) Uani 1 1 d . . . O2 O 0.7272(8) 0.3821(8) 0.3294(8) 0.065(2) Uani 1 1 d D . . H2A H 0.720(5) 0.295(8) 0.405(8) 0.098 Uiso 1 1 d D . . Br1 Br 1.08315(14) 1.33255(9) -0.38403(10) 0.0552(3) Uani 1 1 d . . . Cu1 Cu 0.92193(12) 0.50713(10) 0.16027(11) 0.0399(3) 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 C1 0.033(4) 0.025(3) 0.042(4) -0.012(3) -0.011(3) 0.010(3) C2 0.032(4) 0.033(4) 0.048(4) -0.012(3) -0.001(3) 0.003(3) C3 0.039(4) 0.038(4) 0.051(5) -0.012(4) 0.002(4) -0.008(3) C4 0.047(4) 0.026(3) 0.038(4) -0.011(3) -0.014(3) 0.003(3) C5 0.039(4) 0.032(4) 0.042(4) -0.015(3) -0.012(3) 0.004(3) C6 0.030(3) 0.025(3) 0.035(4) -0.009(3) -0.008(3) 0.007(3) C7 0.038(4) 0.035(4) 0.041(4) -0.011(3) -0.014(3) 0.008(3) C8 0.048(4) 0.071(5) 0.068(5) -0.011(3) -0.019(4) -0.004(3) C9 0.056(4) 0.065(5) 0.077(5) -0.014(4) -0.011(4) 0.009(4) C10 0.063(6) 0.088(7) 0.125(9) -0.017(6) -0.024(6) 0.016(6) C11 0.036(4) 0.035(4) 0.047(4) -0.006(3) -0.015(4) -0.006(3) C12 0.033(4) 0.057(6) 0.058(6) -0.004(4) -0.012(4) 0.008(4) N1 0.028(3) 0.036(3) 0.045(4) -0.012(3) -0.011(3) 0.003(2) N2 0.053(4) 0.028(3) 0.048(4) -0.011(3) -0.021(3) 0.013(3) N3 0.044(5) 0.041(4) 0.116(8) -0.004(5) -0.033(5) 0.009(4) N4 0.064(6) 0.043(5) 0.096(7) -0.001(5) -0.018(5) 0.021(4) O1 0.035(3) 0.028(3) 0.043(3) -0.008(2) 0.003(2) 0.008(2) O2 0.040(3) 0.046(4) 0.063(4) 0.008(3) 0.000(3) -0.004(3) Br1 0.0747(7) 0.0280(4) 0.0489(5) -0.0044(3) -0.0172(5) -0.0024(4) Cu1 0.0337(5) 0.0274(5) 0.0456(6) -0.0058(4) -0.0110(4) 0.0052(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.326(8) . ? C1 C2 1.405(11) . ? C1 C6 1.426(9) . ? C2 C3 1.387(11) . ? C2 H2 0.9300 . ? C3 C4 1.369(12) . ? C3 H3 0.9300 . ? C4 C5 1.355(11) . ? C4 Br1 1.903(7) . ? C5 C6 1.396(10) . ? C5 H5 0.9300 . ? C6 C7 1.434(11) . ? C7 N1 1.284(10) . ? C7 H7 0.9300 . ? C8 C10 1.364(16) . ? C8 C9 1.442(15) . ? C8 N1 1.479(12) . ? C8 H8A 0.9601 . ? C9 O2 1.365(13) . ? C9 H9A 0.9600 . ? C9 H9B 0.9599 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N2 1.155(10) . ? C11 N3 1.279(11) . ? C12 N4 1.132(13) . ? C12 N3 1.294(13) . ? N1 Cu1 1.929(6) . ? N2 Cu1 1.934(7) . ? O1 Cu1 1.913(5) . ? O1 Cu1 2.576(6) 2_765 ? O2 Cu1 1.966(6) . ? O2 H2A 0.850(10) . ? Cu1 O1 2.576(6) 2_765 ? Cu1 Cu1 3.245(2) 2_765 ? 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 C1 C2 118.6(6) . . ? O1 C1 C6 124.7(7) . . ? C2 C1 C6 116.7(6) . . ? C3 C2 C1 122.2(7) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C4 C3 C2 119.4(8) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.7(7) . . ? C5 C4 Br1 120.3(6) . . ? C3 C4 Br1 118.9(6) . . ? C4 C5 C6 121.6(7) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 119.4(7) . . ? C5 C6 C7 117.7(6) . . ? C1 C6 C7 122.9(6) . . ? N1 C7 C6 125.4(7) . . ? N1 C7 H7 117.3 . . ? C6 C7 H7 117.3 . . ? C10 C8 C9 125.5(11) . . ? C10 C8 N1 124.2(11) . . ? C9 C8 N1 109.9(9) . . ? C10 C8 H8A 91.9 . . ? C9 C8 H8A 92.0 . . ? N1 C8 H8A 92.1 . . ? O2 C9 C8 115.7(10) . . ? O2 C9 H9A 108.2 . . ? C8 C9 H9A 109.1 . . ? O2 C9 H9B 108.7 . . ? C8 C9 H9B 107.3 . . ? H9A C9 H9B 107.7 . . ? C8 C10 H10A 109.6 . . ? C8 C10 H10B 109.2 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.6 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 N3 169.5(9) . . ? N4 C12 N3 173.1(11) . . ? C7 N1 C8 119.7(7) . . ? C7 N1 Cu1 125.2(6) . . ? C8 N1 Cu1 114.8(6) . . ? C11 N2 Cu1 170.4(7) . . ? C11 N3 C12 124.0(9) . . ? C1 O1 Cu1 123.9(5) . . ? C1 O1 Cu1 111.2(5) . 2_765 ? Cu1 O1 Cu1 91.4(2) . 2_765 ? C9 O2 Cu1 115.7(6) . . ? C9 O2 H2A 111(2) . . ? Cu1 O2 H2A 133(3) . . ? O1 Cu1 N1 94.0(3) . . ? O1 Cu1 N2 92.4(3) . . ? N1 Cu1 N2 171.1(3) . . ? O1 Cu1 O2 176.0(3) . . ? N1 Cu1 O2 82.0(3) . . ? N2 Cu1 O2 91.6(3) . . ? O1 Cu1 O1 88.6(2) . 2_765 ? N1 Cu1 O1 95.5(2) . 2_765 ? N2 Cu1 O1 90.8(3) . 2_765 ? O2 Cu1 O1 91.6(3) . 2_765 ? O1 Cu1 Cu1 52.54(19) . 2_765 ? N1 Cu1 Cu1 96.8(2) . 2_765 ? N2 Cu1 Cu1 92.1(2) . 2_765 ? O2 Cu1 Cu1 127.6(3) . 2_765 ? O1 Cu1 Cu1 36.10(12) 2_765 2_765 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 176.4(8) . . . . ? C6 C1 C2 C3 -2.0(13) . . . . ? C1 C2 C3 C4 -0.1(14) . . . . ? C2 C3 C4 C5 1.5(14) . . . . ? C2 C3 C4 Br1 -179.6(7) . . . . ? C3 C4 C5 C6 -0.6(13) . . . . ? Br1 C4 C5 C6 -179.5(6) . . . . ? C4 C5 C6 C1 -1.7(12) . . . . ? C4 C5 C6 C7 -179.4(8) . . . . ? O1 C1 C6 C5 -175.4(8) . . . . ? C2 C1 C6 C5 2.9(11) . . . . ? O1 C1 C6 C7 2.1(13) . . . . ? C2 C1 C6 C7 -179.6(8) . . . . ? C5 C6 C7 N1 -179.3(8) . . . . ? C1 C6 C7 N1 3.1(13) . . . . ? C10 C8 C9 O2 174.9(15) . . . . ? N1 C8 C9 O2 -11.8(17) . . . . ? C6 C7 N1 C8 -178.1(9) . . . . ? C6 C7 N1 Cu1 8.0(12) . . . . ? C10 C8 N1 C7 14.2(19) . . . . ? C9 C8 N1 C7 -159.2(10) . . . . ? C10 C8 N1 Cu1 -171.2(13) . . . . ? C9 C8 N1 Cu1 15.4(13) . . . . ? N3 C11 N2 Cu1 125(6) . . . . ? N2 C11 N3 C12 170(5) . . . . ? N4 C12 N3 C11 174(11) . . . . ? C2 C1 O1 Cu1 164.2(6) . . . . ? C6 C1 O1 Cu1 -17.5(11) . . . . ? C2 C1 O1 Cu1 -88.9(8) . . . 2_765 ? C6 C1 O1 Cu1 89.4(8) . . . 2_765 ? C8 C9 O2 Cu1 3.3(16) . . . . ? C1 O1 Cu1 N1 21.4(7) . . . . ? Cu1 O1 Cu1 N1 -95.5(2) 2_765 . . . ? C1 O1 Cu1 N2 -152.4(7) . . . . ? Cu1 O1 Cu1 N2 90.8(3) 2_765 . . . ? C1 O1 Cu1 O2 23(5) . . . . ? Cu1 O1 Cu1 O2 -93(5) 2_765 . . . ? C1 O1 Cu1 O1 116.8(7) . . . 2_765 ? Cu1 O1 Cu1 O1 0.0 2_765 . . 2_765 ? C1 O1 Cu1 Cu1 116.8(7) . . . 2_765 ? C7 N1 Cu1 O1 -17.0(7) . . . . ? C8 N1 Cu1 O1 168.8(7) . . . . ? C7 N1 Cu1 N2 118.7(19) . . . . ? C8 N1 Cu1 N2 -56(2) . . . . ? C7 N1 Cu1 O2 163.1(8) . . . . ? C8 N1 Cu1 O2 -11.1(7) . . . . ? C7 N1 Cu1 O1 -106.0(7) . . . 2_765 ? C8 N1 Cu1 O1 79.8(7) . . . 2_765 ? C7 N1 Cu1 Cu1 -69.7(7) . . . 2_765 ? C8 N1 Cu1 Cu1 116.1(7) . . . 2_765 ? C11 N2 Cu1 O1 -85(4) . . . . ? C11 N2 Cu1 N1 140(4) . . . . ? C11 N2 Cu1 O2 96(4) . . . . ? C11 N2 Cu1 O1 4(4) . . . 2_765 ? C11 N2 Cu1 Cu1 -32(4) . . . 2_765 ? C9 O2 Cu1 O1 2(5) . . . . ? C9 O2 Cu1 N1 4.5(9) . . . . ? C9 O2 Cu1 N2 178.2(9) . . . . ? C9 O2 Cu1 O1 -90.9(9) . . . 2_765 ? C9 O2 Cu1 Cu1 -88.0(9) . . . 2_765 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.38 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.991 _refine_diff_density_min -1.025 _refine_diff_density_rms 0.154 _database_code_depnum_ccdc_archive 'CCDC 933907' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dingshuai1109282_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 Br2 Cu2 N8 O4' _chemical_formula_weight 773.40 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' Br Br -0.2901 2.4595 '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 9.518(4) _cell_length_b 11.058(4) _cell_length_c 14.814(6) _cell_angle_alpha 92.275(7) _cell_angle_beta 105.925(7) _cell_angle_gamma 109.584(6) _cell_volume 1397.6(10) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1585 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 26.96 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.03 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 764 _exptl_absorpt_coefficient_mu 4.427 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.49044 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 10226 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0781 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 28.23 _reflns_number_total 6831 _reflns_number_gt 2435 _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^)+(0.0615P)^2^+3.9868P] 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 6831 _refine_ls_number_parameters 366 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.1529 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1906 _refine_ls_wR_factor_gt 0.1619 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.004 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.0678(2) 0.0165(2) 0.90028(15) 0.0557(7) Uani 1 1 d U . . Br2 Br 1.4322(2) 0.4836(2) 0.59943(15) 0.0561(7) Uani 1 1 d U . . Cu2 Cu 0.7019(3) 0.3691(2) 0.70889(16) 0.0417(7) Uani 1 1 d U . . Cu1 Cu 0.7983(3) 0.1309(2) 0.79108(16) 0.0411(7) Uani 1 1 d U . . O2 O 0.6596(13) -0.0509(11) 0.7797(8) 0.060(3) Uani 1 1 d DU . . H2 H 0.579(7) -0.078(8) 0.798(6) 0.090 Uiso 1 1 d D . . O4 O 0.8391(13) 0.5507(11) 0.7233(8) 0.060(3) Uani 1 1 d U . . H4 H 0.8615 0.5837 0.6759 0.072 Uiso 1 1 d R . . O1 O 0.9360(12) 0.3048(10) 0.7960(7) 0.039(2) Uani 1 1 d U . . N1 N 0.8270(15) 0.0657(13) 0.6759(9) 0.039(2) Uani 1 1 d U . . N5 N 0.6717(15) 0.4338(13) 0.8229(10) 0.041(3) Uani 1 1 d U . . N2 N 0.7716(15) 0.1714(13) 0.9131(10) 0.044(3) Uani 1 1 d U . . O3 O 0.5656(12) 0.1950(10) 0.7044(8) 0.042(2) Uani 1 1 d U . . N6 N 0.7262(15) 0.3276(14) 0.5869(10) 0.045(3) Uani 1 1 d U . . C11 C 1.2759(18) 0.4240(17) 0.6614(12) 0.036(3) Uani 1 1 d U . . C13 C 0.4480(19) 0.2459(17) 0.8222(12) 0.037(3) Uani 1 1 d U . . C14 C 0.2233(19) 0.0767(17) 0.8371(12) 0.037(3) Uani 1 1 d U . . C2 C 0.3314(18) 0.1984(17) 0.8662(12) 0.045(3) Uani 1 1 d U . . H2A H 0.3282 0.2509 0.9157 0.054 Uiso 1 1 calc R . . C3 C 0.4539(18) 0.1633(16) 0.7469(12) 0.035(3) Uani 1 1 d U . . C4 C 1.0459(18) 0.3352(16) 0.7518(12) 0.035(3) Uani 1 1 d U . . N4 N 0.5144(19) 0.1761(16) 1.1181(12) 0.080(5) Uani 1 1 d U . . C6 C 0.741(2) 0.2021(18) 0.9790(13) 0.044(3) Uani 1 1 d U . . C7 C 1.1673(17) 0.3019(17) 0.6325(11) 0.041(3) Uani 1 1 d U . . H7 H 1.1695 0.2496 0.5826 0.049 Uiso 1 1 calc R . . C8 C 1.0508(18) 0.2538(17) 0.6780(11) 0.034(3) Uani 1 1 d U . . C9 C 0.2240(19) -0.0043(17) 0.7642(13) 0.047(4) Uani 1 1 d U . . H9 H 0.1478 -0.0869 0.7445 0.057 Uiso 1 1 calc R . . C10 C 0.756(2) 0.2987(18) 0.5211(13) 0.044(3) Uani 1 1 d U . . C1 C 0.872(2) 0.6297(17) 0.8093(12) 0.080(4) Uani 1 1 d U . . H1A H 0.8390 0.7003 0.7909 0.096 Uiso 1 1 d R . . H1C H 0.9823 0.6662 0.8432 0.096 Uiso 1 1 d R . . N3 N 0.7347(18) 0.2472(15) 1.0585(11) 0.070(4) Uani 1 1 d U . . C5 C 0.3387(18) 0.0389(16) 0.7213(12) 0.042(3) Uani 1 1 d U . . H5 H 0.3400 -0.0169 0.6731 0.051 Uiso 1 1 calc R . . C12 C 1.2793(18) 0.5047(16) 0.7364(12) 0.046(4) Uani 1 1 d U . . H12 H 1.3567 0.5867 0.7565 0.055 Uiso 1 1 calc R . . C15 C 1.1651(18) 0.4608(16) 0.7812(11) 0.041(3) Uani 1 1 d U . . H15 H 1.1663 0.5146 0.8315 0.049 Uiso 1 1 calc R . . N8 N 0.9894(19) 0.3205(16) 0.3835(11) 0.081(5) Uani 1 1 d U . . N7 N 0.7682(17) 0.2540(15) 0.4462(11) 0.067(4) Uani 1 1 d U . . C16 C 0.9406(18) 0.1270(16) 0.6455(11) 0.040(3) Uani 1 1 d U . . H16 H 0.9520 0.0820 0.5952 0.048 Uiso 1 1 calc R . . C17 C 0.784(2) 0.5658(19) 0.8668(13) 0.076(4) Uani 1 1 d U . . H17 H 0.8618 0.5292 0.8931 0.091 Uiso 1 1 d R . . C18 C 0.5613(19) 0.3763(16) 0.8572(12) 0.044(3) Uani 1 1 d U . . H18 H 0.5531 0.4216 0.9086 0.053 Uiso 1 1 calc R . . C19 C 0.888(2) 0.2982(18) 0.4131(13) 0.052(4) Uani 1 1 d U . . C1A C 0.6532(19) -0.1273(16) 0.7040(11) 0.069(4) Uani 1 1 d DU . . H1AA H 0.5431 -0.1732 0.6744 0.083 Uiso 1 1 d R . . H1AB H 0.7004 -0.1903 0.7229 0.083 Uiso 1 1 d R . . C1B C 0.716(2) -0.0654(19) 0.6315(13) 0.071(4) Uani 1 1 d U . . H1B H 0.6322 -0.0369 0.6017 0.085 Uiso 1 1 d R . . C1C C 0.610(2) 0.206(2) 1.0823(14) 0.059(4) Uani 1 1 d U . . C21 C 0.707(2) -0.1248(18) 0.5485(13) 0.095(5) Uani 1 1 d U . . H21A H 0.6940 -0.0700 0.5007 0.142 Uiso 1 1 calc R . . H21B H 0.6186 -0.2050 0.5310 0.142 Uiso 1 1 calc R . . H21C H 0.8009 -0.1422 0.5544 0.142 Uiso 1 1 calc R . . C22 C 0.798(2) 0.616(2) 0.9589(15) 0.111(6) Uani 1 1 d U . . H22A H 0.6966 0.5906 0.9677 0.166 Uiso 1 1 calc R . . H22B H 0.8438 0.7093 0.9673 0.166 Uiso 1 1 calc R . . H22C H 0.8641 0.5836 1.0046 0.166 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 Br1 0.0443(14) 0.0648(17) 0.0644(16) 0.0208(13) 0.0330(12) 0.0133(12) Br2 0.0464(15) 0.0636(17) 0.0639(16) 0.0202(13) 0.0321(12) 0.0133(12) Cu2 0.0440(14) 0.0385(15) 0.0448(15) -0.0001(12) 0.0270(11) 0.0078(11) Cu1 0.0429(14) 0.0392(15) 0.0429(14) 0.0001(12) 0.0244(11) 0.0085(12) O2 0.066(5) 0.043(5) 0.063(5) -0.007(4) 0.040(4) -0.004(4) O4 0.066(4) 0.043(4) 0.061(5) -0.007(4) 0.040(4) -0.009(4) O1 0.045(3) 0.033(4) 0.048(4) -0.002(3) 0.028(3) 0.013(3) N1 0.042(4) 0.038(4) 0.038(4) -0.005(4) 0.021(4) 0.010(4) N5 0.043(4) 0.037(4) 0.038(4) -0.006(4) 0.020(4) 0.004(4) N2 0.046(4) 0.049(5) 0.044(5) 0.002(4) 0.025(4) 0.018(4) O3 0.046(4) 0.035(4) 0.050(4) -0.003(3) 0.028(3) 0.012(3) N6 0.049(4) 0.050(5) 0.042(5) 0.002(4) 0.027(4) 0.014(4) C11 0.035(5) 0.041(6) 0.042(6) 0.014(5) 0.024(5) 0.015(5) C13 0.039(4) 0.037(4) 0.040(5) 0.003(4) 0.021(4) 0.012(4) C14 0.035(6) 0.040(6) 0.043(6) 0.013(5) 0.019(5) 0.015(5) C2 0.044(5) 0.045(5) 0.047(5) 0.002(5) 0.018(5) 0.015(5) C3 0.038(4) 0.034(4) 0.039(4) 0.003(4) 0.020(4) 0.013(4) C4 0.036(4) 0.037(4) 0.037(4) 0.004(4) 0.018(4) 0.013(4) N4 0.089(10) 0.084(11) 0.080(11) 0.009(9) 0.058(9) 0.023(9) C6 0.038(5) 0.048(5) 0.044(5) 0.004(5) 0.020(4) 0.008(4) C7 0.040(5) 0.045(5) 0.041(5) 0.001(5) 0.021(4) 0.013(4) C8 0.035(4) 0.037(4) 0.035(4) 0.004(4) 0.020(4) 0.013(4) C9 0.039(6) 0.040(6) 0.056(6) 0.000(6) 0.018(5) 0.004(5) C10 0.036(5) 0.046(5) 0.044(5) 0.004(5) 0.017(4) 0.003(4) C1 0.086(7) 0.057(7) 0.065(7) -0.012(6) 0.037(6) -0.021(6) N3 0.063(6) 0.071(6) 0.059(6) -0.020(6) 0.032(6) -0.005(6) C5 0.045(5) 0.033(5) 0.047(6) -0.003(5) 0.022(5) 0.006(5) C12 0.038(6) 0.040(6) 0.050(6) 0.001(5) 0.017(5) 0.000(5) C15 0.047(5) 0.032(5) 0.044(5) -0.005(5) 0.024(5) 0.009(5) N8 0.089(10) 0.079(10) 0.074(10) -0.007(9) 0.057(8) 0.006(9) N7 0.058(6) 0.071(6) 0.057(6) -0.017(6) 0.034(5) -0.007(6) C16 0.049(4) 0.038(4) 0.041(4) 0.003(4) 0.026(4) 0.015(4) C17 0.083(6) 0.048(6) 0.059(6) -0.013(6) 0.028(6) -0.025(6) C18 0.050(4) 0.039(4) 0.045(4) -0.003(4) 0.026(4) 0.010(4) C19 0.069(7) 0.044(7) 0.039(6) -0.011(6) 0.032(6) 0.005(6) C1A 0.082(7) 0.049(6) 0.062(6) -0.008(6) 0.039(6) -0.007(6) C1B 0.084(6) 0.046(6) 0.055(6) -0.014(6) 0.030(6) -0.014(6) C1C 0.071(7) 0.052(7) 0.045(7) -0.006(7) 0.026(6) 0.005(7) C21 0.103(8) 0.081(8) 0.083(8) -0.018(6) 0.049(6) 0.000(6) C22 0.117(9) 0.101(9) 0.095(9) -0.014(7) 0.049(7) 0.005(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 Br1 C14 1.912(17) . ? Br2 C11 1.905(16) . ? Cu2 O3 1.914(10) . ? Cu2 N5 1.938(13) . ? Cu2 N6 1.941(14) . ? Cu2 O4 1.960(11) . ? Cu1 O1 1.915(10) . ? Cu1 N2 1.949(14) . ? Cu1 N1 1.949(13) . ? Cu1 O2 1.971(11) . ? O2 C1A 1.352(18) . ? O4 C1 1.410(18) . ? O1 C4 1.340(17) . ? N1 C16 1.278(17) . ? N1 C1B 1.471(19) . ? N5 C18 1.281(18) . ? N5 C17 1.481(19) . ? N2 C6 1.16(2) . ? O3 C3 1.336(17) . ? N6 C10 1.15(2) . ? C11 C7 1.36(2) . ? C11 C12 1.38(2) . ? C13 C2 1.40(2) . ? C13 C3 1.44(2) . ? C13 C18 1.45(2) . ? C14 C2 1.36(2) . ? C14 C9 1.38(2) . ? C3 C5 1.399(19) . ? C4 C8 1.41(2) . ? C4 C15 1.425(19) . ? N4 C1C 1.14(2) . ? C6 N3 1.28(2) . ? C7 C8 1.42(2) . ? C8 C16 1.41(2) . ? C9 C5 1.37(2) . ? C10 N7 1.25(2) . ? C1 C17 1.41(2) . ? N3 C1C 1.27(2) . ? C12 C15 1.39(2) . ? N8 C19 1.13(2) . ? N7 C19 1.31(2) . ? C17 C22 1.41(2) . ? C1A C1B 1.46(2) . ? C1B C21 1.34(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 O3 Cu2 N5 94.1(5) . . ? O3 Cu2 N6 91.9(5) . . ? N5 Cu2 N6 171.0(6) . . ? O3 Cu2 O4 175.4(5) . . ? N5 Cu2 O4 81.3(5) . . ? N6 Cu2 O4 92.7(5) . . ? O1 Cu1 N2 92.4(5) . . ? O1 Cu1 N1 94.2(5) . . ? N2 Cu1 N1 171.2(6) . . ? O1 Cu1 O2 176.8(5) . . ? N2 Cu1 O2 90.8(5) . . ? N1 Cu1 O2 82.6(5) . . ? C1A O2 Cu1 113.2(11) . . ? C1 O4 Cu2 117.1(11) . . ? C4 O1 Cu1 123.4(10) . . ? C16 N1 C1B 122.3(16) . . ? C16 N1 Cu1 122.8(12) . . ? C1B N1 Cu1 114.7(11) . . ? C18 N5 C17 120.1(16) . . ? C18 N5 Cu2 125.9(13) . . ? C17 N5 Cu2 113.9(11) . . ? C6 N2 Cu1 170.7(16) . . ? C3 O3 Cu2 123.9(11) . . ? C10 N6 Cu2 171.3(16) . . ? C7 C11 C12 121.9(17) . . ? C7 C11 Br2 119.0(13) . . ? C12 C11 Br2 119.0(14) . . ? C2 C13 C3 119.3(16) . . ? C2 C13 C18 117.9(16) . . ? C3 C13 C18 122.8(17) . . ? C2 C14 C9 121.7(18) . . ? C2 C14 Br1 118.7(14) . . ? C9 C14 Br1 119.6(14) . . ? C14 C2 C13 120.5(17) . . ? O3 C3 C5 118.7(15) . . ? O3 C3 C13 124.5(16) . . ? C5 C3 C13 116.7(16) . . ? O1 C4 C8 125.1(16) . . ? O1 C4 C15 116.8(15) . . ? C8 C4 C15 118.0(16) . . ? N2 C6 N3 169(2) . . ? C11 C7 C8 120.5(16) . . ? C16 C8 C4 122.3(17) . . ? C16 C8 C7 118.4(15) . . ? C4 C8 C7 119.3(16) . . ? C5 C9 C14 119.0(17) . . ? N6 C10 N7 171(2) . . ? C17 C1 O4 112.2(15) . . ? C6 N3 C1C 121.2(18) . . ? C9 C5 C3 122.8(17) . . ? C11 C12 C15 118.8(16) . . ? C12 C15 C4 121.4(15) . . ? C10 N7 C19 126.7(17) . . ? N1 C16 C8 128.5(17) . . ? C22 C17 C1 125.4(18) . . ? C22 C17 N5 120.8(18) . . ? C1 C17 N5 113.8(16) . . ? N5 C18 C13 125.0(17) . . ? N8 C19 N7 171(2) . . ? O2 C1A C1B 118.4(16) . . ? C21 C1B C1A 126.2(19) . . ? C21 C1B N1 124.8(19) . . ? C1A C1B N1 107.1(15) . . ? N4 C1C N3 169(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.752 _refine_diff_density_min -0.795 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 933908' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dingshuai110923_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 Br2 Cu2 N8 O4' _chemical_formula_weight 745.34 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' Br Br -0.2901 2.4595 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.724(3) _cell_length_b 13.478(3) _cell_length_c 15.482(7) _cell_angle_alpha 90.00 _cell_angle_beta 117.98(2) _cell_angle_gamma 90.00 _cell_volume 2529.0(14) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.49 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.958 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 4.889 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.49044 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 18375 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6272 _reflns_number_gt 4865 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+0.2874P] 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 6272 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 Br1 Br 0.88618(2) 0.067280(17) 0.789468(17) 0.04149(7) Uani 1 1 d . . . Br2 Br -0.37719(2) 0.36142(2) -0.290801(19) 0.04911(8) Uani 1 1 d . . . Cu1 Cu 0.46077(2) 0.231005(19) 0.30367(2) 0.03313(8) Uani 1 1 d . . . Cu2 Cu 0.04954(2) 0.503184(18) 0.20167(2) 0.03251(8) Uani 1 1 d . . . O1 O 0.00511(13) 0.39552(11) 0.11431(12) 0.0367(4) Uani 1 1 d . . . O2 O 0.07510(13) 0.61511(11) 0.29686(12) 0.0408(4) Uani 1 1 d . . . H2A H 0.0865 0.5908 0.3508 0.061 Uiso 1 1 d R . . O3 O 0.50929(12) 0.11789(10) 0.38425(11) 0.0345(4) Uani 1 1 d . . . O4 O 0.43896(13) 0.34458(11) 0.21063(11) 0.0392(4) Uani 1 1 d . . . H4 H 0.4256 0.3199 0.1569 0.059 Uiso 1 1 d R . . N1 N 0.57884(14) 0.31340(12) 0.39404(13) 0.0310(4) Uani 1 1 d . . . N2 N 0.32648(17) 0.16889(16) 0.20573(16) 0.0492(6) Uani 1 1 d . . . N3 N 0.1601(2) 0.12771(17) 0.05558(19) 0.0689(8) Uani 1 1 d . . . N4 N 0.1181(2) -0.03118(19) -0.03079(17) 0.0591(6) Uani 1 1 d . . . N5 N 0.3903(2) 0.23532(18) 0.53408(18) 0.0588(6) Uani 1 1 d . . . N6 N 0.3394(2) 0.3238(2) 0.38131(19) 0.0703(8) Uani 1 1 d . . . N7 N 0.18049(17) 0.43193(16) 0.29442(16) 0.0468(5) Uani 1 1 d . . . N8 N -0.06136(14) 0.59166(12) 0.11249(13) 0.0291(4) Uani 1 1 d . . . C1 C 0.59402(17) 0.11144(15) 0.47084(15) 0.0271(4) Uani 1 1 d . . . C2 C 0.61954(17) 0.01811(15) 0.51795(17) 0.0317(5) Uani 1 1 d . . . H2 H 0.5783 -0.0369 0.4844 0.038 Uiso 1 1 calc R . . C3 C 0.70263(17) 0.00596(15) 0.61099(17) 0.0317(5) Uani 1 1 d . . . H3 H 0.7154 -0.0560 0.6408 0.038 Uiso 1 1 calc R . . C4 C 0.76814(17) 0.08651(16) 0.66100(15) 0.0298(4) Uani 1 1 d . . . C5 C 0.75071(17) 0.17811(16) 0.61816(16) 0.0307(5) Uani 1 1 d . . . H5 H 0.7962 0.2310 0.6520 0.037 Uiso 1 1 calc R . . C6 C 0.66353(16) 0.19237(15) 0.52249(15) 0.0268(4) Uani 1 1 d . . . C7 C 0.65248(17) 0.28888(15) 0.48020(16) 0.0312(5) Uani 1 1 d . . . H7 H 0.7025 0.3374 0.5181 0.037 Uiso 1 1 calc R . . C8 C 0.5747(2) 0.41375(16) 0.35631(18) 0.0438(6) Uani 1 1 d . . . H8A H 0.6471 0.4442 0.3889 0.053 Uiso 1 1 calc R . . H8B H 0.5237 0.4544 0.3680 0.053 Uiso 1 1 calc R . . C9 C 0.5366(2) 0.40558(18) 0.24804(19) 0.0450(6) Uani 1 1 d . . . H9A H 0.5197 0.4706 0.2176 0.054 Uiso 1 1 calc R . . H9B H 0.5930 0.3748 0.2360 0.054 Uiso 1 1 calc R . . C10 C 0.2503(2) 0.14543(18) 0.13532(19) 0.0447(6) Uani 1 1 d . . . C11 C 0.1420(2) 0.0415(2) 0.01196(18) 0.0464(6) Uani 1 1 d . . . C12 C 0.3630(2) 0.28037(19) 0.4641(2) 0.0450(6) Uani 1 1 d . . . C13 C 0.2538(2) 0.38149(19) 0.33890(19) 0.0441(6) Uani 1 1 d . . . C14 C -0.0203(2) 0.67965(17) 0.26059(18) 0.0383(5) Uani 1 1 d . . . H14A H -0.0009 0.7435 0.2933 0.046 Uiso 1 1 calc R . . H14B H -0.0783 0.6502 0.2713 0.046 Uiso 1 1 calc R . . C15 C -0.05749(19) 0.69124(15) 0.15290(17) 0.0357(5) Uani 1 1 d . . . H15A H -0.1299 0.7218 0.1208 0.043 Uiso 1 1 calc R . . H15B H -0.0062 0.7330 0.1428 0.043 Uiso 1 1 calc R . . C16 C -0.13363(17) 0.57101(15) 0.02456(16) 0.0306(5) Uani 1 1 d . . . H16 H -0.1815 0.6215 -0.0119 0.037 Uiso 1 1 calc R . . C17 C -0.14658(17) 0.47629(15) -0.02208(16) 0.0291(4) Uani 1 1 d . . . C18 C -0.23387(18) 0.46600(17) -0.11720(16) 0.0334(5) Uani 1 1 d . . . H18 H -0.2778 0.5206 -0.1485 0.040 Uiso 1 1 calc R . . C19 C -0.25513(18) 0.37679(16) -0.16434(17) 0.0344(5) Uani 1 1 d . . . C20 C -0.19001(19) 0.29445(17) -0.11842(18) 0.0386(5) Uani 1 1 d . . . H20 H -0.2055 0.2337 -0.1506 0.046 Uiso 1 1 calc R . . C21 C -0.10265(19) 0.30253(16) -0.02549(18) 0.0358(5) Uani 1 1 d . . . H21 H -0.0591 0.2471 0.0037 0.043 Uiso 1 1 calc R . . C22 C -0.07781(17) 0.39317(15) 0.02645(16) 0.0290(4) 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 Br1 0.04851(15) 0.03639(13) 0.02932(13) 0.00284(9) 0.00975(11) 0.01071(10) Br2 0.04896(15) 0.05306(16) 0.03761(15) -0.01270(11) 0.01391(12) -0.00060(12) Cu1 0.03354(15) 0.02939(14) 0.02782(14) 0.00113(10) 0.00721(11) -0.00431(11) Cu2 0.03141(14) 0.02851(14) 0.03250(15) 0.00385(11) 0.01076(12) 0.00266(10) O1 0.0385(9) 0.0290(8) 0.0372(9) 0.0031(7) 0.0134(7) 0.0066(7) O2 0.0444(9) 0.0337(8) 0.0331(9) 0.0006(7) 0.0087(8) -0.0041(7) O3 0.0351(8) 0.0283(8) 0.0315(8) 0.0012(6) 0.0084(7) -0.0054(6) O4 0.0464(9) 0.0341(8) 0.0288(8) 0.0006(7) 0.0108(7) -0.0016(7) N1 0.0317(9) 0.0231(8) 0.0308(10) 0.0029(7) 0.0086(8) -0.0002(7) N2 0.0440(12) 0.0476(12) 0.0405(13) 0.0000(10) 0.0069(10) -0.0098(10) N3 0.0533(14) 0.0515(14) 0.0560(16) -0.0035(12) -0.0125(12) -0.0011(11) N4 0.0586(15) 0.0682(15) 0.0366(13) -0.0110(12) 0.0108(11) -0.0047(12) N5 0.0715(17) 0.0586(14) 0.0420(14) 0.0112(12) 0.0231(13) 0.0186(12) N6 0.0536(14) 0.104(2) 0.0593(17) 0.0410(15) 0.0315(13) 0.0377(15) N7 0.0398(11) 0.0512(12) 0.0406(12) 0.0102(10) 0.0115(10) 0.0079(10) N8 0.0318(9) 0.0228(8) 0.0324(10) -0.0001(7) 0.0149(8) 0.0001(7) C1 0.0272(10) 0.0277(10) 0.0288(11) -0.0001(8) 0.0151(9) 0.0001(8) C2 0.0323(11) 0.0248(10) 0.0392(13) 0.0002(9) 0.0177(10) -0.0023(8) C3 0.0338(11) 0.0268(10) 0.0379(12) 0.0061(9) 0.0197(10) 0.0044(9) C4 0.0297(11) 0.0330(11) 0.0264(11) 0.0028(8) 0.0129(9) 0.0065(9) C5 0.0298(11) 0.0309(11) 0.0290(11) -0.0017(9) 0.0117(9) -0.0001(9) C6 0.0257(10) 0.0253(10) 0.0284(11) 0.0020(8) 0.0119(9) 0.0006(8) C7 0.0290(11) 0.0271(10) 0.0326(12) -0.0021(9) 0.0104(9) -0.0038(8) C8 0.0487(14) 0.0266(11) 0.0387(14) 0.0051(10) 0.0061(11) -0.0027(10) C9 0.0525(15) 0.0321(12) 0.0441(15) 0.0103(11) 0.0174(12) -0.0013(11) C10 0.0436(14) 0.0396(13) 0.0410(15) 0.0039(11) 0.0115(12) -0.0047(11) C11 0.0372(13) 0.0583(16) 0.0287(13) 0.0035(12) 0.0030(11) -0.0041(12) C12 0.0369(13) 0.0519(15) 0.0427(15) 0.0038(12) 0.0157(12) 0.0109(11) C13 0.0377(13) 0.0547(15) 0.0385(14) 0.0116(12) 0.0166(12) 0.0017(12) C14 0.0456(13) 0.0305(11) 0.0399(13) -0.0052(10) 0.0210(11) -0.0035(10) C15 0.0400(12) 0.0257(10) 0.0384(13) -0.0025(9) 0.0160(11) 0.0007(9) C16 0.0306(11) 0.0269(10) 0.0344(12) 0.0046(9) 0.0153(9) 0.0047(8) C17 0.0318(11) 0.0267(10) 0.0331(12) 0.0019(9) 0.0188(10) 0.0012(8) C18 0.0352(12) 0.0332(11) 0.0333(12) 0.0007(9) 0.0173(10) 0.0025(9) C19 0.0353(12) 0.0377(12) 0.0326(12) -0.0043(9) 0.0178(10) -0.0020(9) C20 0.0431(13) 0.0330(11) 0.0466(14) -0.0114(10) 0.0268(12) -0.0036(10) C21 0.0394(12) 0.0288(11) 0.0428(14) 0.0014(10) 0.0221(11) 0.0056(9) C22 0.0304(11) 0.0273(10) 0.0352(12) 0.0021(9) 0.0202(10) 0.0006(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C4 1.904(2) . ? Br2 C19 1.899(2) . ? Cu1 O3 1.8827(15) . ? Cu1 N1 1.9207(18) . ? Cu1 N2 1.943(2) . ? Cu1 O4 2.0257(16) . ? Cu2 O1 1.8796(16) . ? Cu2 N8 1.9165(18) . ? Cu2 N7 1.947(2) . ? Cu2 O2 2.0213(17) . ? O1 C22 1.302(3) . ? O2 C14 1.448(3) . ? O2 H2A 0.8400 . ? O3 C1 1.302(3) . ? O4 C9 1.442(3) . ? O4 H4 0.8325 . ? N1 C7 1.283(3) . ? N1 C8 1.464(3) . ? N2 C10 1.145(3) . ? N3 C10 1.296(3) . ? N3 C11 1.308(4) . ? N4 C11 1.141(3) . ? N5 C12 1.142(3) . ? N6 C13 1.301(3) . ? N6 C12 1.303(4) . ? N7 C13 1.140(3) . ? N8 C16 1.284(3) . ? N8 C15 1.471(3) . ? C1 C2 1.413(3) . ? C1 C6 1.422(3) . ? C2 C3 1.364(3) . ? C2 H2 0.9300 . ? C3 C4 1.390(3) . ? C3 H3 0.9300 . ? C4 C5 1.368(3) . ? C5 C6 1.414(3) . ? C5 H5 0.9300 . ? C6 C7 1.432(3) . ? C7 H7 0.9300 . ? C8 C9 1.508(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C14 C15 1.505(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.436(3) . ? C16 H16 0.9300 . ? C17 C18 1.403(3) . ? C17 C22 1.430(3) . ? C18 C19 1.365(3) . ? C18 H18 0.9300 . ? C19 C20 1.393(3) . ? C20 C21 1.379(3) . ? C20 H20 0.9300 . ? C21 C22 1.414(3) . ? C21 H21 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 O3 Cu1 N1 94.03(7) . . ? O3 Cu1 N2 94.55(8) . . ? N1 Cu1 N2 170.02(8) . . ? O3 Cu1 O4 166.28(7) . . ? N1 Cu1 O4 82.75(7) . . ? N2 Cu1 O4 90.06(8) . . ? O1 Cu2 N8 94.71(7) . . ? O1 Cu2 N7 91.46(8) . . ? N8 Cu2 N7 169.82(8) . . ? O1 Cu2 O2 170.96(7) . . ? N8 Cu2 O2 82.44(7) . . ? N7 Cu2 O2 92.64(8) . . ? C22 O1 Cu2 126.88(13) . . ? C14 O2 Cu2 110.46(13) . . ? C14 O2 H2A 109.4 . . ? Cu2 O2 H2A 108.7 . . ? C1 O3 Cu1 127.15(13) . . ? C9 O4 Cu1 110.23(13) . . ? C9 O4 H4 110.9 . . ? Cu1 O4 H4 107.3 . . ? C7 N1 C8 121.16(18) . . ? C7 N1 Cu1 126.33(15) . . ? C8 N1 Cu1 112.45(14) . . ? C10 N2 Cu1 165.9(2) . . ? C10 N3 C11 121.4(2) . . ? C13 N6 C12 120.9(2) . . ? C13 N7 Cu2 170.9(2) . . ? C16 N8 C15 120.31(18) . . ? C16 N8 Cu2 125.90(15) . . ? C15 N8 Cu2 113.78(14) . . ? O3 C1 C2 118.44(18) . . ? O3 C1 C6 124.56(18) . . ? C2 C1 C6 116.99(19) . . ? C3 C2 C1 122.3(2) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? C2 C3 C4 119.74(19) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.9(2) . . ? C5 C4 Br1 119.92(16) . . ? C3 C4 Br1 119.11(16) . . ? C4 C5 C6 120.0(2) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 119.96(18) . . ? C5 C6 C7 117.28(18) . . ? C1 C6 C7 122.70(19) . . ? N1 C7 C6 124.91(19) . . ? N1 C7 H7 117.5 . . ? C6 C7 H7 117.5 . . ? N1 C8 C9 107.73(19) . . ? N1 C8 H8A 110.2 . . ? C9 C8 H8A 110.2 . . ? N1 C8 H8B 110.2 . . ? C9 C8 H8B 110.2 . . ? H8A C8 H8B 108.5 . . ? O4 C9 C8 105.1(2) . . ? O4 C9 H9A 110.7 . . ? C8 C9 H9A 110.7 . . ? O4 C9 H9B 110.7 . . ? C8 C9 H9B 110.7 . . ? H9A C9 H9B 108.8 . . ? N2 C10 N3 174.2(3) . . ? N4 C11 N3 174.7(3) . . ? N5 C12 N6 172.6(3) . . ? N7 C13 N6 173.7(3) . . ? O2 C14 C15 105.45(18) . . ? O2 C14 H14A 110.7 . . ? C15 C14 H14A 110.7 . . ? O2 C14 H14B 110.7 . . ? C15 C14 H14B 110.7 . . ? H14A C14 H14B 108.8 . . ? N8 C15 C14 107.59(17) . . ? N8 C15 H15A 110.2 . . ? C14 C15 H15A 110.2 . . ? N8 C15 H15B 110.2 . . ? C14 C15 H15B 110.2 . . ? H15A C15 H15B 108.5 . . ? N8 C16 C17 125.30(19) . . ? N8 C16 H16 117.4 . . ? C17 C16 H16 117.4 . . ? C18 C17 C22 120.1(2) . . ? C18 C17 C16 117.32(19) . . ? C22 C17 C16 122.5(2) . . ? C19 C18 C17 120.8(2) . . ? C19 C18 H18 119.6 . . ? C17 C18 H18 119.6 . . ? C18 C19 C20 120.3(2) . . ? C18 C19 Br2 120.75(17) . . ? C20 C19 Br2 118.94(17) . . ? C21 C20 C19 120.4(2) . . ? C21 C20 H20 119.8 . . ? C19 C20 H20 119.8 . . ? C20 C21 C22 121.4(2) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? O1 C22 C21 118.34(19) . . ? O1 C22 C17 124.61(19) . . ? C21 C22 C17 117.0(2) . . ? 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 N8 Cu2 O1 C22 -2.18(18) . . . . ? N7 Cu2 O1 C22 -174.08(18) . . . . ? O2 Cu2 O1 C22 69.0(5) . . . . ? O1 Cu2 O2 C14 -52.5(5) . . . . ? N8 Cu2 O2 C14 19.57(14) . . . . ? N7 Cu2 O2 C14 -169.38(15) . . . . ? N1 Cu1 O3 C1 1.59(18) . . . . ? N2 Cu1 O3 C1 -173.30(18) . . . . ? O4 Cu1 O3 C1 77.4(3) . . . . ? O3 Cu1 O4 C9 -59.3(3) . . . . ? N1 Cu1 O4 C9 17.84(15) . . . . ? N2 Cu1 O4 C9 -169.10(16) . . . . ? O3 Cu1 N1 C7 -5.0(2) . . . . ? N2 Cu1 N1 C7 144.2(5) . . . . ? O4 Cu1 N1 C7 -171.6(2) . . . . ? O3 Cu1 N1 C8 177.93(17) . . . . ? N2 Cu1 N1 C8 -32.9(6) . . . . ? O4 Cu1 N1 C8 11.33(16) . . . . ? O3 Cu1 N2 C10 -150.3(10) . . . . ? N1 Cu1 N2 C10 60.5(12) . . . . ? O4 Cu1 N2 C10 16.8(10) . . . . ? O1 Cu2 N7 C13 11.5(14) . . . . ? N8 Cu2 N7 C13 -115.9(13) . . . . ? O2 Cu2 N7 C13 -176.6(14) . . . . ? O1 Cu2 N8 C16 -0.97(19) . . . . ? N7 Cu2 N8 C16 126.2(5) . . . . ? O2 Cu2 N8 C16 -172.34(19) . . . . ? O1 Cu2 N8 C15 179.88(15) . . . . ? N7 Cu2 N8 C15 -53.0(6) . . . . ? O2 Cu2 N8 C15 8.51(15) . . . . ? Cu1 O3 C1 C2 -177.32(15) . . . . ? Cu1 O3 C1 C6 3.0(3) . . . . ? O3 C1 C2 C3 -175.9(2) . . . . ? C6 C1 C2 C3 3.8(3) . . . . ? C1 C2 C3 C4 -2.6(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C2 C3 C4 Br1 -178.34(16) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? Br1 C4 C5 C6 179.58(16) . . . . ? C4 C5 C6 C1 0.0(3) . . . . ? C4 C5 C6 C7 -177.4(2) . . . . ? O3 C1 C6 C5 177.25(19) . . . . ? C2 C1 C6 C5 -2.5(3) . . . . ? O3 C1 C6 C7 -5.5(3) . . . . ? C2 C1 C6 C7 174.8(2) . . . . ? C8 N1 C7 C6 -179.2(2) . . . . ? Cu1 N1 C7 C6 3.9(3) . . . . ? C5 C6 C7 N1 179.1(2) . . . . ? C1 C6 C7 N1 1.8(4) . . . . ? C7 N1 C8 C9 145.6(2) . . . . ? Cu1 N1 C8 C9 -37.1(2) . . . . ? Cu1 O4 C9 C8 -41.0(2) . . . . ? N1 C8 C9 O4 50.1(3) . . . . ? Cu1 N2 C10 N3 -68(4) . . . . ? C11 N3 C10 N2 -178(100) . . . . ? C10 N3 C11 N4 173(3) . . . . ? C13 N6 C12 N5 160(2) . . . . ? Cu2 N7 C13 N6 46(4) . . . . ? C12 N6 C13 N7 -169(3) . . . . ? Cu2 O2 C14 C15 -41.54(19) . . . . ? C16 N8 C15 C14 147.1(2) . . . . ? Cu2 N8 C15 C14 -33.7(2) . . . . ? O2 C14 C15 N8 47.7(2) . . . . ? C15 N8 C16 C17 -178.9(2) . . . . ? Cu2 N8 C16 C17 2.0(3) . . . . ? N8 C16 C17 C18 176.9(2) . . . . ? N8 C16 C17 C22 -0.1(3) . . . . ? C22 C17 C18 C19 0.6(3) . . . . ? C16 C17 C18 C19 -176.5(2) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? C17 C18 C19 Br2 177.22(16) . . . . ? C18 C19 C20 C21 -0.8(4) . . . . ? Br2 C19 C20 C21 -178.19(18) . . . . ? C19 C20 C21 C22 1.2(4) . . . . ? Cu2 O1 C22 C21 -175.57(15) . . . . ? Cu2 O1 C22 C17 4.4(3) . . . . ? C20 C21 C22 O1 179.3(2) . . . . ? C20 C21 C22 C17 -0.6(3) . . . . ? C18 C17 C22 O1 179.8(2) . . . . ? C16 C17 C22 O1 -3.3(3) . . . . ? C18 C17 C22 C21 -0.3(3) . . . . ? C16 C17 C22 C21 176.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.646 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 933909'