# Electronic Supplementary Material (ESI) for Chemical Communications # 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_avs213 _audit_creation_date 2012-10-29T12:01:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic # _chemical_name_systematic ; ? ; _chemical_formula_sum 'C23 H26 Cu2 N2 O8' _chemical_formula_weight 585.54 _symmetry_space_group_name_H-M 'C 2/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 28.265(5) _cell_length_b 13.127(5) _cell_length_c 8.729(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 106.779(5) _cell_angle_gamma 90.000(5) _cell_volume 3101(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_description prysm _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_special_details ; ? ; _exptl_absorpt_coefficient_mu 1.411 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS-2008/1 - Bruker AXS' _exptl_absorpt_correction_T_min 0.569 _exptl_absorpt_correction_T_max 0.745 _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0865 _diffrn_reflns_av_unetI/netI 0.0822 _diffrn_reflns_number 17018 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 28.1 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_max 0.948 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 3590 _reflns_number_gt 2621 _reflns_threshold_expression >2\s(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _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^ > 2\s(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^)+(0.0522P)^2^+17.9248P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3590 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_gt 0.0653 _refine_ls_wR_factor_ref 0.1556 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.683 _refine_diff_density_min -1.16 _refine_diff_density_rms 0.104 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 0 '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 0.006 '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' 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 N1A N 0.35033(14) 0.1271(3) 0.2581(5) 0.0292(9) Uani 1 1 d . . . C2A C 0.3853(2) 0.1801(4) 0.3628(7) 0.0453(14) Uani 1 1 d . . . H2A H 0.3848 0.2507 0.3536 0.054 Uiso 1 1 calc R . . C3A C 0.4220(2) 0.1365(4) 0.4838(7) 0.0484(15) Uani 1 1 d . . . H3A H 0.4463 0.1773 0.5501 0.058 Uiso 1 1 calc R . . C4A C 0.42294(18) 0.0322(4) 0.5073(6) 0.0336(11) Uani 1 1 d . . . C5A C 0.3853(2) -0.0234(4) 0.4018(7) 0.0418(13) Uani 1 1 d . . . H5A H 0.3841 -0.0938 0.4115 0.05 Uiso 1 1 calc R . . C6A C 0.34981(19) 0.0264(4) 0.2830(6) 0.0407(13) Uani 1 1 d . . . H6A H 0.3243 -0.0118 0.2169 0.049 Uiso 1 1 calc R . . C7A C 0.46206(19) -0.0239(4) 0.6342(6) 0.0379(12) Uani 1 1 d . . . H7A1 H 0.4794 -0.0695 0.5813 0.046 Uiso 1 1 calc R . . H7A2 H 0.4457 -0.0656 0.6953 0.046 Uiso 1 1 calc R . . C8A C 0.5 0.0426(6) 0.75 0.0372(17) Uani 1 2 d S . . H8A1 H 0.4836 0.0859 0.809 0.045 Uiso 0.5 1 calc PR . . H8A2 H 0.5164 0.0859 0.691 0.045 Uiso 0.5 1 calc PR . . C3B C 0.2119(2) 0.0775(3) -0.1070(6) 0.0317(11) Uani 1 1 d . . . C4B C 0.1899(2) -0.0211(4) -0.1743(6) 0.0365(12) Uani 1 1 d . . . H4B1 H 0.201 -0.0365 -0.267 0.044 Uiso 1 1 calc R . . H4B2 H 0.1543 -0.0129 -0.2113 0.044 Uiso 1 1 calc R . . C5B C 0.2015(2) -0.1117(3) -0.0622(6) 0.0335(12) Uani 1 1 d . . . H5B1 H 0.1854 -0.1029 0.0211 0.04 Uiso 1 1 calc R . . H5B2 H 0.2369 -0.1148 -0.0116 0.04 Uiso 1 1 calc R . . C6B C 0.1843(2) -0.2122(4) -0.1504(6) 0.0333(11) Uani 1 1 d . . . H6B1 H 0.1914 -0.2676 -0.0737 0.04 Uiso 1 1 calc R . . H6B2 H 0.1487 -0.2097 -0.198 0.04 Uiso 1 1 calc R . . C7B C 0.29141(18) 0.2663(3) -0.2206(6) 0.0274(10) Uani 1 1 d . . . O1B O 0.25418(13) 0.0790(2) -0.0077(4) 0.0372(9) Uani 1 1 d . . . O2B O 0.31394(13) 0.3433(2) 0.1535(4) 0.0354(8) Uani 1 1 d . . . O8B O 0.31595(14) 0.2208(3) -0.0981(4) 0.0425(10) Uani 1 1 d . . . O9B O 0.25206(13) 0.2056(3) 0.2459(4) 0.0391(8) Uani 1 1 d . . . Cu1 Cu 0.29007(2) 0.20364(4) 0.08704(6) 0.02366(18) 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 N1A 0.028(2) 0.029(2) 0.028(2) 0.0037(17) 0.0032(18) 0.0020(17) C2A 0.054(4) 0.029(3) 0.047(3) -0.006(2) 0.005(3) 0.007(2) C3A 0.050(4) 0.041(3) 0.044(3) -0.010(3) -0.002(3) 0.003(3) C4A 0.032(3) 0.043(3) 0.024(3) 0.003(2) 0.007(2) -0.002(2) C5A 0.043(3) 0.035(3) 0.040(3) 0.010(2) 0.001(3) -0.007(2) C6A 0.035(3) 0.038(3) 0.039(3) 0.003(2) -0.007(2) -0.009(2) C7A 0.036(3) 0.048(3) 0.023(3) 0.001(2) -0.003(2) 0.001(2) C8A 0.036(4) 0.045(4) 0.028(4) 0 0.003(3) 0 C3B 0.053(3) 0.021(2) 0.025(3) -0.0061(19) 0.017(2) -0.001(2) C4B 0.048(3) 0.027(3) 0.029(3) -0.003(2) 0.004(2) -0.001(2) C5B 0.060(4) 0.022(2) 0.025(3) -0.0050(19) 0.022(2) -0.006(2) C6B 0.047(3) 0.025(2) 0.033(3) -0.004(2) 0.019(2) -0.008(2) C7B 0.036(3) 0.019(2) 0.029(3) 0.0013(18) 0.012(2) 0.0025(19) O1B 0.039(2) 0.0220(17) 0.040(2) -0.0027(15) -0.0056(17) 0.0021(15) O2B 0.038(2) 0.0209(17) 0.043(2) 0.0012(15) 0.0055(17) -0.0001(15) O8B 0.053(2) 0.046(2) 0.034(2) 0.0160(17) 0.0206(18) 0.0244(18) O9B 0.040(2) 0.049(2) 0.0298(18) 0.0094(17) 0.0112(16) 0.0033(18) Cu1 0.0289(3) 0.0193(3) 0.0214(3) 0.0028(2) 0.0051(2) 0.0036(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N1A C2A 1.331(7) . ? N1A C6A 1.340(6) . ? N1A Cu1 2.161(4) . ? C2A C3A 1.374(8) . ? C3A C4A 1.383(8) . ? C4A C5A 1.395(7) . ? C4A C7A 1.512(7) . ? C5A C6A 1.382(7) . ? C7A C8A 1.519(6) . ? C8A C7A 1.519(6) 2_656 ? C3B O1B 1.257(6) . ? C3B O2B 1.269(6) 7 ? C3B C4B 1.482(7) . ? C4B C5B 1.515(7) . ? C5B C6B 1.534(6) . ? C6B C7B 1.506(6) 4_544 ? C7B O9B 1.240(6) 7 ? C7B O8B 1.246(6) . ? C7B C6B 1.506(6) 4_554 ? O1B Cu1 1.976(3) . ? O2B C3B 1.269(6) 7 ? O2B Cu1 1.981(3) . ? O8B Cu1 1.970(4) . ? O9B C7B 1.240(6) 7 ? O9B Cu1 1.985(4) . ? Cu1 Cu1 2.6332(12) 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 C2A N1A C6A 116.4(4) . . ? C2A N1A Cu1 120.8(3) . . ? C6A N1A Cu1 121.8(3) . . ? N1A C2A C3A 123.8(5) . . ? C2A C3A C4A 120.3(5) . . ? C3A C4A C5A 116.2(5) . . ? C3A C4A C7A 124.7(5) . . ? C5A C4A C7A 119.0(5) . . ? C6A C5A C4A 119.8(5) . . ? N1A C6A C5A 123.3(5) . . ? C4A C7A C8A 115.7(5) . . ? C7A C8A C7A 109.9(6) . 2_656 ? O1B C3B O2B 123.6(4) . 7 ? O1B C3B C4B 119.6(4) . . ? O2B C3B C4B 116.8(5) 7 . ? C3B C4B C5B 116.3(4) . . ? C4B C5B C6B 111.9(4) . . ? C7B C6B C5B 112.9(4) 4_544 . ? O9B C7B O8B 125.0(5) 7 . ? O9B C7B C6B 117.0(4) 7 4_554 ? O8B C7B C6B 118.1(4) . 4_554 ? C3B O1B Cu1 124.9(3) . . ? C3B O2B Cu1 123.3(3) 7 . ? C7B O8B Cu1 120.8(3) . . ? C7B O9B Cu1 126.0(3) 7 . ? O8B Cu1 O1B 91.09(17) . . ? O8B Cu1 O2B 87.62(16) . . ? O1B Cu1 O2B 168.17(14) . . ? O8B Cu1 O9B 167.41(14) . . ? O1B Cu1 O9B 89.27(16) . . ? O2B Cu1 O9B 89.46(15) . . ? O8B Cu1 N1A 102.41(15) . . ? O1B Cu1 N1A 96.39(14) . . ? O2B Cu1 N1A 95.38(14) . . ? O9B Cu1 N1A 90.05(15) . . ? O8B Cu1 Cu1 86.27(11) . 7 ? O1B Cu1 Cu1 83.64(10) . 7 ? O2B Cu1 Cu1 84.54(10) . 7 ? O9B Cu1 Cu1 81.26(11) . 7 ? N1A Cu1 Cu1 171.31(11) . 7 ? _database_code_depnum_ccdc_archive 'CCDC 941413' ####################################################################### # # 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_anto1p1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 Cu2 N2 O8' _chemical_formula_weight 585.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3240 0.8257 '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 27.449(18) _cell_length_b 13.1546(14) _cell_length_c 8.4882(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.58(3) _cell_angle_gamma 90.00 _cell_volume 2966(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour green _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 1100000(100000) _diffrn_radiation_wavelength 0.30969 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6303 _diffrn_reflns_av_R_equivalents 0.0916 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 10.48 _reflns_number_total 1244 _reflns_number_gt 933 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. Intensities corrected for disorder solvent included in voids using the Squeeze utility P. v.d. Sluis and A. L. Spek, Acta Crystallogr., Sect A 1990, 46, 194-201 ; _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^)+(0.1367P)^2^+11.9420P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1244 _refine_ls_number_parameters 65 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0797 _refine_ls_wR_factor_ref 0.2425 _refine_ls_wR_factor_gt 0.2255 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.116 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.79102(11) 0.20514(8) 0.08436(15) 0.0389(12) Uani 1 1 d . . . N1A N 0.8500(3) 0.1305(4) 0.2592(6) 0.033(2) Uiso 1 1 d G . . C2A C 0.8475(4) 0.0261(4) 0.2814(7) 0.040(3) Uiso 1 1 d G . . H2A H 0.8223 -0.0119 0.2130 0.048 Uiso 1 1 calc R . . C3A C 0.8828(4) -0.0215(3) 0.4059(8) 0.045(3) Uiso 1 1 d G . . H3A H 0.8812 -0.0913 0.4207 0.054 Uiso 1 1 calc R . . C4A C 0.9206(4) 0.0353(4) 0.5081(7) 0.033(2) Uiso 1 1 d GD . . C5A C 0.9230(3) 0.1397(4) 0.4860(7) 0.039(3) Uiso 1 1 d G . . H5A H 0.9483 0.1777 0.5544 0.047 Uiso 1 1 calc R . . C6A C 0.8877(4) 0.1873(3) 0.3615(8) 0.040(3) Uiso 1 1 d G . . H6A H 0.8893 0.2571 0.3467 0.048 Uiso 1 1 calc R . . C7A C 0.9615(4) -0.0219(6) 0.6347(9) 0.036(3) Uiso 1 1 d D . . H71A H 0.9451 -0.0644 0.6996 0.043 Uiso 1 1 calc R . . H72A H 0.9794 -0.0665 0.5775 0.043 Uiso 1 1 calc R . . C8A C 1.0000 0.0462(9) 0.7500 0.037(4) Uiso 1 2 d SD . . H81A H 0.9831 0.0894 0.8123 0.044 Uiso 0.50 1 calc PR . . H82A H 1.0169 0.0894 0.6877 0.044 Uiso 0.50 1 calc PR . . O1B O 0.8187(6) 0.2204(5) -0.1093(9) 0.045(2) Uiso 1 1 d D . . O2B O 0.7538(5) 0.2094(5) 0.2535(10) 0.046(2) Uiso 1 1 d . . . C3B C 0.7912(5) 0.2644(7) -0.2329(10) 0.028(2) Uiso 1 1 d D . . C4B C 0.8158(6) 0.2882(6) -0.3728(12) 0.033(2) Uiso 1 1 d D . . H41B H 0.8520 0.2911 -0.3302 0.040 Uiso 1 1 calc R . . H42B H 0.8082 0.2338 -0.4523 0.040 Uiso 1 1 calc R . . C5B C 0.7972(6) 0.3895(5) -0.4569(10) 0.029(2) Uiso 1 1 d D . . H51B H 0.8123 0.4005 -0.5472 0.034 Uiso 1 1 calc R . . H52B H 0.7609 0.3873 -0.4996 0.034 Uiso 1 1 calc R . . C6B C 0.8115(7) 0.4769(5) -0.3339(10) 0.037(3) Uiso 1 1 d D . . H61B H 0.8478 0.4849 -0.3042 0.044 Uiso 1 1 calc R . . H62B H 0.8011 0.4598 -0.2360 0.044 Uiso 1 1 calc R . . C7B C 0.7868(5) 0.5780(6) -0.4023(11) 0.029(2) Uiso 1 1 d D . . O8B O 0.7558(5) 0.0800(5) -0.0048(9) 0.0411(19) Uiso 1 1 d . . . O9B O 0.8127(5) 0.3445(5) 0.1418(9) 0.043(2) 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 0.061(4) 0.0270(7) 0.0309(8) 0.0021(5) 0.0163(13) 0.0037(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O9B 1.951(9) . ? Cu1 O2B 1.960(10) . ? Cu1 O8B 1.962(9) . ? Cu1 O1B 1.988(9) . ? Cu1 N1A 2.139(7) . ? Cu1 Cu1 2.625(5) 7_655 ? N1A C2A 1.3900 . ? N1A C6A 1.3900 . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C4A C5A 1.3900 . ? C4A C7A 1.541(5) . ? C5A C6A 1.3900 . ? C7A C8A 1.536(5) . ? C8A C7A 1.536(5) 2_756 ? O1B C3B 1.267(9) . ? O2B C3B 1.253(9) 7_655 ? C3B O2B 1.253(9) 7_655 ? C3B C4B 1.538(5) . ? C4B C5B 1.537(5) . ? C5B C6B 1.537(5) . ? C6B C7B 1.538(5) . ? C7B O8B 1.236(9) 4_654 ? C7B O9B 1.245(9) 6_565 ? O8B C7B 1.236(9) 4_644 ? O9B C7B 1.245(9) 6_566 ? 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 O9B Cu1 O2B 88.4(4) . . ? O9B Cu1 O8B 167.0(4) . . ? O2B Cu1 O8B 90.5(4) . . ? O9B Cu1 O1B 87.4(3) . . ? O2B Cu1 O1B 168.8(4) . . ? O8B Cu1 O1B 91.1(4) . . ? O9B Cu1 N1A 97.4(4) . . ? O2B Cu1 N1A 87.0(4) . . ? O8B Cu1 N1A 95.5(4) . . ? O1B Cu1 N1A 103.9(4) . . ? O9B Cu1 Cu1 83.1(4) . 7_655 ? O2B Cu1 Cu1 81.6(4) . 7_655 ? O8B Cu1 Cu1 84.0(4) . 7_655 ? O1B Cu1 Cu1 87.6(4) . 7_655 ? N1A Cu1 Cu1 168.5(2) . 7_655 ? C2A N1A C6A 120.0 . . ? C2A N1A Cu1 119.6(4) . . ? C6A N1A Cu1 120.1(3) . . ? C3A C2A N1A 120.0 . . ? C2A C3A C4A 120.0 . . ? C5A C4A C3A 120.0 . . ? C5A C4A C7A 121.7(5) . . ? C3A C4A C7A 118.1(5) . . ? C4A C5A C6A 120.0 . . ? C5A C6A N1A 120.0 . . ? C8A C7A C4A 115.0(5) . . ? C7A C8A C7A 108.6(9) . 2_756 ? C3B O1B Cu1 117.3(9) . . ? C3B O2B Cu1 125.7(7) 7_655 . ? O2B C3B O1B 127.1(9) 7_655 . ? O2B C3B C4B 116.4(9) 7_655 . ? O1B C3B C4B 116.5(9) . . ? C5B C4B C3B 112.1(8) . . ? C6B C5B C4B 109.5(7) . . ? C5B C6B C7B 112.2(7) . . ? O8B C7B O9B 123.4(10) 4_654 6_565 ? O8B C7B C6B 121.0(9) 4_654 . ? O9B C7B C6B 115.6(9) 6_565 . ? C7B O8B Cu1 124.1(7) 4_644 . ? C7B O9B Cu1 125.4(9) 6_566 . ? 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 C3B C4B C5B C6B 61.9(14) . . . . ? C4B C5B C6B C7B -171.0(11) . . . . ? C5B C6B C7B O8B 34.9(16) . . . 4_654 ? C5B C4B C3B O1B -144.1(10) . . . . ? _diffrn_measured_fraction_theta_max 0.494 _diffrn_reflns_theta_full 10.48 _diffrn_measured_fraction_theta_full 0.494 _refine_diff_density_max 0.511 _refine_diff_density_min -0.468 _refine_diff_density_rms 0.107 _database_code_depnum_ccdc_archive 'CCDC 941414' ####################################################################### # # 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_anto2p0 _database_code_depnum_ccdc_archive 'CCDC 941415' #TrackingRef '- 2_Pccn_revised.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 Cu2 N2 O8' _chemical_formula_weight 585.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3240 0.8257 '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 26.834(18) _cell_length_b 12.9913(14) _cell_length_c 8.4037(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.52(3) _cell_angle_gamma 90.00 _cell_volume 2848.5(19) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour green _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 2000000(100000) _diffrn_radiation_wavelength 0.30969 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6010 _diffrn_reflns_av_R_equivalents 0.0889 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 10.48 _reflns_number_total 1192 _reflns_number_gt 905 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. Intensities corrected for disorder solvent included in voids using the Squeeze utility P. v.d. Sluis and A. L. Spek, Acta Crystallogr., Sect A 1990, 46, 194-201 ; _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^)+(0.1466P)^2^+31.0659P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1192 _refine_ls_number_parameters 64 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1161 _refine_ls_R_factor_gt 0.0947 _refine_ls_wR_factor_ref 0.2787 _refine_ls_wR_factor_gt 0.2638 _refine_ls_goodness_of_fit_ref 1.141 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.79120(12) 0.20446(9) 0.08321(17) 0.0264(13) Uani 1 1 d . . . N1A N 0.8494(4) 0.1296(5) 0.2564(8) 0.033(2) Uiso 1 1 d G . . C2A C 0.8469(4) 0.0237(5) 0.2765(9) 0.041(3) Uiso 1 1 d G . . H2A H 0.8217 -0.0145 0.2066 0.049 Uiso 1 1 calc R . . C3A C 0.8823(5) -0.0252(4) 0.4010(10) 0.043(3) Uiso 1 1 d G . . H3A H 0.8806 -0.0961 0.4144 0.052 Uiso 1 1 calc R . . C4A C 0.9201(4) 0.0318(5) 0.5054(9) 0.030(3) Uiso 1 1 d GD . . C5A C 0.9226(4) 0.1378(5) 0.4854(9) 0.037(3) Uiso 1 1 d G . . H5A H 0.9478 0.1759 0.5552 0.045 Uiso 1 1 calc R . . C6A C 0.8872(5) 0.1867(4) 0.3609(9) 0.037(3) Uiso 1 1 d G . . H6A H 0.8889 0.2575 0.3474 0.044 Uiso 1 1 calc R . . C7A C 0.9616(4) -0.0245(6) 0.6326(11) 0.033(3) Uiso 1 1 d D . . H71A H 0.9448 -0.0686 0.6972 0.039 Uiso 1 1 calc R . . H72A H 0.9806 -0.0686 0.5748 0.039 Uiso 1 1 calc R . . C8A C 1.0000 0.0443(9) 0.7500 0.029(4) Uiso 1 2 d SD . . H81A H 0.9820 0.0880 0.8116 0.035 Uiso 0.50 1 calc PR . . H82A H 1.0180 0.0880 0.6884 0.035 Uiso 0.50 1 calc PR . . O1B O 0.8192(7) 0.2193(7) -0.1124(11) 0.052(3) Uiso 1 1 d D . . O2B O 0.7526(6) 0.2092(7) 0.2557(12) 0.050(3) Uiso 1 1 d . . . C3B C 0.7927(6) 0.2618(8) -0.2375(11) 0.025(3) Uiso 1 1 d D . . C4B C 0.8190(8) 0.2833(7) -0.3781(14) 0.035(3) Uiso 1 1 d D . . H41B H 0.8113 0.2284 -0.4583 0.042 Uiso 1 1 calc R . . H42B H 0.8559 0.2858 -0.3359 0.042 Uiso 1 1 calc R . . C5B C 0.7999(8) 0.3867(7) -0.4593(12) 0.034(3) Uiso 1 1 d D . . H51B H 0.7630 0.3845 -0.4993 0.041 Uiso 1 1 calc R . . H52B H 0.8150 0.3984 -0.5520 0.041 Uiso 1 1 calc R . . C6B C 0.8146(8) 0.4753(7) -0.3357(12) 0.038(3) Uiso 1 1 d D . . H61B H 0.8044 0.4577 -0.2357 0.046 Uiso 1 1 calc R . . H62B H 0.8515 0.4840 -0.3092 0.046 Uiso 1 1 calc R . . C7B C 0.7890(6) 0.5773(7) -0.4030(14) 0.031(3) Uiso 1 1 d D . . O8B O 0.7547(6) 0.0790(6) -0.0045(12) 0.047(3) Uiso 1 1 d . . . O9B O 0.8160(7) 0.3446(7) 0.1401(12) 0.047(3) 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 0.021(4) 0.0306(9) 0.0252(9) 0.0018(5) 0.0001(14) 0.0026(9) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O8B 1.954(11) . ? Cu1 O9B 1.958(11) . ? Cu1 O2B 1.970(11) . ? Cu1 O1B 1.971(12) . ? Cu1 N1A 2.108(8) . ? Cu1 Cu1 2.608(5) 7_655 ? N1A C2A 1.3900 . ? N1A C6A 1.3900 . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C4A C5A 1.3900 . ? C4A C7A 1.538(5) . ? C5A C6A 1.3900 . ? C7A C8A 1.536(5) . ? C8A C7A 1.536(5) 2_756 ? O1B C3B 1.252(9) . ? O2B C3B 1.246(10) 7_655 ? C3B O2B 1.246(10) 7_655 ? C3B C4B 1.538(5) . ? C4B C5B 1.539(5) . ? C5B C6B 1.539(5) . ? C6B C7B 1.538(5) . ? C7B O8B 1.246(10) 4_654 ? C7B O9B 1.251(9) 6_565 ? O8B C7B 1.246(10) 4_644 ? O9B C7B 1.251(9) 6_566 ? 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 O8B Cu1 O9B 168.1(5) . . ? O8B Cu1 O2B 90.0(5) . . ? O9B Cu1 O2B 89.9(4) . . ? O8B Cu1 O1B 91.3(5) . . ? O9B Cu1 O1B 86.5(4) . . ? O2B Cu1 O1B 168.5(5) . . ? O8B Cu1 N1A 95.8(4) . . ? O9B Cu1 N1A 96.0(5) . . ? O2B Cu1 N1A 86.5(5) . . ? O1B Cu1 N1A 104.8(5) . . ? O8B Cu1 Cu1 83.6(4) . 7_655 ? O9B Cu1 Cu1 84.6(4) . 7_655 ? O2B Cu1 Cu1 81.6(4) . 7_655 ? O1B Cu1 Cu1 87.1(5) . 7_655 ? N1A Cu1 Cu1 168.1(3) . 7_655 ? C2A N1A C6A 120.0 . . ? C2A N1A Cu1 119.4(4) . . ? C6A N1A Cu1 120.3(4) . . ? C3A C2A N1A 120.0 . . ? C2A C3A C4A 120.0 . . ? C5A C4A C3A 120.0 . . ? C5A C4A C7A 120.5(6) . . ? C3A C4A C7A 119.3(6) . . ? C4A C5A C6A 120.0 . . ? C5A C6A N1A 120.0 . . ? C8A C7A C4A 116.0(6) . . ? C7A C8A C7A 108.8(9) . 2_756 ? C3B O1B Cu1 119.3(11) . . ? C3B O2B Cu1 125.7(9) 7_655 . ? O2B C3B O1B 125.7(12) 7_655 . ? O2B C3B C4B 117.4(11) 7_655 . ? O1B C3B C4B 116.8(11) . . ? C3B C4B C5B 109.5(9) . . ? C4B C5B C6B 110.3(8) . . ? C7B C6B C5B 112.0(9) . . ? O8B C7B O9B 124.2(11) 4_654 6_565 ? O8B C7B C6B 121.3(11) 4_654 . ? O9B C7B C6B 114.4(10) 6_565 . ? C7B O8B Cu1 124.5(8) 4_644 . ? C7B O9B Cu1 122.9(11) 6_566 . ? 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 C3B C4B C5B C6B 62.6(17) . . . . ? C4B C5B C6B C7B -170.8(13) . . . . ? _diffrn_measured_fraction_theta_max 0.493 _diffrn_reflns_theta_full 10.48 _diffrn_measured_fraction_theta_full 0.493 _refine_diff_density_max 0.588 _refine_diff_density_min -0.589 _refine_diff_density_rms 0.123 ####################################################################### # # 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_anto3p6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 Cu2 N2 O8' _chemical_formula_weight 585.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3240 0.8257 '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 26.161(15) _cell_length_b 12.7057(12) _cell_length_c 8.2557(10) _cell_angle_alpha 90.00 _cell_angle_beta 102.02(3) _cell_angle_gamma 90.00 _cell_volume 2684.0(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour green _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 3600000(100000) _diffrn_radiation_wavelength 0.30969 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5792 _diffrn_reflns_av_R_equivalents 0.0887 _diffrn_reflns_av_sigmaI/netI 0.0618 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 10.49 _reflns_number_total 1086 _reflns_number_gt 893 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. Intensities corrected for disorder solvent included in voids using the Squeeze utility P. v.d. Sluis and A. L. Spek, Acta Crystallogr., Sect A 1990, 46, 194-201 ; _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^)+(0.1763P)^2^+39.4583P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1086 _refine_ls_number_parameters 65 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1197 _refine_ls_R_factor_gt 0.1027 _refine_ls_wR_factor_ref 0.3099 _refine_ls_wR_factor_gt 0.2909 _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_restrained_S_all 1.143 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.79122(12) 0.20307(11) 0.08082(19) 0.0314(15) Uani 1 1 d . . . N1A N 0.8502(4) 0.1286(6) 0.2535(9) 0.031(3) Uiso 1 1 d G . . C2A C 0.8487(5) 0.0203(6) 0.2754(10) 0.039(4) Uiso 1 1 d G . . H2A H 0.8237 -0.0200 0.2056 0.047 Uiso 1 1 calc R . . C3A C 0.8846(5) -0.0278(4) 0.4016(10) 0.041(4) Uiso 1 1 d G . . H3A H 0.8836 -0.1003 0.4163 0.049 Uiso 1 1 calc R . . C4A C 0.9220(4) 0.0324(6) 0.5059(9) 0.024(3) Uiso 1 1 d GD . . C5A C 0.9235(4) 0.1407(6) 0.4840(9) 0.033(3) Uiso 1 1 d G . . H5A H 0.9485 0.1810 0.5538 0.040 Uiso 1 1 calc R . . C6A C 0.8876(5) 0.1888(4) 0.3578(10) 0.031(3) Uiso 1 1 d G . . H6A H 0.8886 0.2613 0.3431 0.037 Uiso 1 1 calc R . . C7A C 0.9628(5) -0.0278(7) 0.6331(12) 0.029(3) Uiso 1 1 d D . . H71A H 0.9449 -0.0729 0.6982 0.035 Uiso 1 1 calc R . . H72A H 0.9830 -0.0725 0.5748 0.035 Uiso 1 1 calc R . . C8A C 1.0000 0.0454(11) 0.7500 0.025(4) Uiso 1 2 d SD . . H81A H 0.9808 0.0899 0.8119 0.031 Uiso 0.50 1 calc PR . . H82A H 1.0192 0.0899 0.6881 0.031 Uiso 0.50 1 calc PR . . O1B O 0.8208(8) 0.2165(9) -0.1188(14) 0.058(3) Uiso 1 1 d D . . O2B O 0.7536(7) 0.2111(9) 0.2595(14) 0.053(3) Uiso 1 1 d . . . C3B C 0.7926(7) 0.2582(9) -0.2441(13) 0.024(3) Uiso 1 1 d D . . C4B C 0.8201(9) 0.2776(9) -0.3884(17) 0.036(3) Uiso 1 1 d D . . H41B H 0.8124 0.2211 -0.4687 0.043 Uiso 1 1 calc R . . H42B H 0.8576 0.2811 -0.3483 0.043 Uiso 1 1 calc R . . C5B C 0.7994(9) 0.3831(8) -0.4683(14) 0.033(3) Uiso 1 1 d D . . H51B H 0.8129 0.3954 -0.5677 0.040 Uiso 1 1 calc R . . H52B H 0.7615 0.3819 -0.4985 0.040 Uiso 1 1 calc R . . C6B C 0.8178(9) 0.4706(8) -0.3408(14) 0.030(3) Uiso 1 1 d D . . H61B H 0.8077 0.4541 -0.2372 0.036 Uiso 1 1 calc R . . H62B H 0.8556 0.4768 -0.3197 0.036 Uiso 1 1 calc R . . C7B C 0.7924(7) 0.5745(8) -0.4112(15) 0.028(3) Uiso 1 1 d D . . O8B O 0.7535(7) 0.0756(9) -0.0056(15) 0.051(3) Uiso 1 1 d . . . O9B O 0.8185(8) 0.3440(9) 0.1349(14) 0.049(3) 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 0.047(4) 0.0226(10) 0.0238(10) 0.0021(6) 0.0053(17) 0.0037(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2B 1.939(12) . ? Cu1 O9B 1.945(14) . ? Cu1 O8B 1.952(14) . ? Cu1 O1B 1.969(13) . ? Cu1 N1A 2.096(9) . ? Cu1 Cu1 2.580(6) 7_655 ? N1A C2A 1.3900 . ? N1A C6A 1.3900 . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C4A C5A 1.3900 . ? C4A C7A 1.536(5) . ? C5A C6A 1.3900 . ? C7A C8A 1.534(5) . ? C8A C7A 1.534(5) 2_756 ? O1B C3B 1.256(10) . ? O2B C3B 1.249(10) 7_655 ? C3B O2B 1.249(10) 7_655 ? C3B C4B 1.536(5) . ? C4B C5B 1.541(5) . ? C5B C6B 1.539(5) . ? C6B C7B 1.536(5) . ? C7B O8B 1.254(10) 4_654 ? C7B O9B 1.256(9) 6_565 ? O8B C7B 1.254(10) 4_644 ? O9B C7B 1.256(9) 6_566 ? 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 O2B Cu1 O9B 89.9(5) . . ? O2B Cu1 O8B 91.3(5) . . ? O9B Cu1 O8B 168.8(6) . . ? O2B Cu1 O1B 169.3(5) . . ? O9B Cu1 O1B 85.6(5) . . ? O8B Cu1 O1B 91.3(6) . . ? O2B Cu1 N1A 85.7(5) . . ? O9B Cu1 N1A 94.3(6) . . ? O8B Cu1 N1A 96.8(5) . . ? O1B Cu1 N1A 104.3(6) . . ? O2B Cu1 Cu1 82.3(5) . 7_655 ? O9B Cu1 Cu1 85.5(5) . 7_655 ? O8B Cu1 Cu1 83.7(5) . 7_655 ? O1B Cu1 Cu1 87.6(5) . 7_655 ? N1A Cu1 Cu1 168.1(3) . 7_655 ? C2A N1A C6A 120.0 . . ? C2A N1A Cu1 119.9(5) . . ? C6A N1A Cu1 119.7(5) . . ? N1A C2A C3A 120.0 . . ? C4A C3A C2A 120.0 . . ? C3A C4A C5A 120.0 . . ? C3A C4A C7A 116.6(7) . . ? C5A C4A C7A 123.2(7) . . ? C6A C5A C4A 120.0 . . ? C5A C6A N1A 120.0 . . ? C8A C7A C4A 112.8(7) . . ? C7A C8A C7A 105.4(10) . 2_756 ? C3B O1B Cu1 117.4(12) . . ? C3B O2B Cu1 124.9(10) 7_655 . ? O2B C3B O1B 127.3(12) 7_655 . ? O2B C3B C4B 118.0(13) 7_655 . ? O1B C3B C4B 114.6(12) . . ? C3B C4B C5B 107.0(10) . . ? C6B C5B C4B 107.7(10) . . ? C7B C6B C5B 108.2(10) . . ? O8B C7B O9B 123.8(14) 4_654 6_565 ? O8B C7B C6B 120.5(13) 4_654 . ? O9B C7B C6B 115.3(13) 6_565 . ? C7B O8B Cu1 124.3(10) 4_644 . ? C7B O9B Cu1 122.6(14) 6_566 . ? 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 C3B C4B C5B C6B 65.8(17) . . . . ? C4B C5B C6B C7B -173.7(14) . . . . ? _diffrn_measured_fraction_theta_max 0.476 _diffrn_reflns_theta_full 10.49 _diffrn_measured_fraction_theta_full 0.476 _refine_diff_density_max 0.595 _refine_diff_density_min -0.649 _refine_diff_density_rms 0.162 _database_code_depnum_ccdc_archive 'CCDC 941416' ####################################################################### # # 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_anto4p5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_formula_sum 'C23 H26 Cu2 N2 O8' _chemical_formula_weight 585.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 '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 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3240 0.8257 '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 25.74(3) _cell_length_b 12.6140(19) _cell_length_c 8.2015(19) _cell_angle_alpha 90.00 _cell_angle_beta 101.42(6) _cell_angle_gamma 90.00 _cell_volume 2610(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _exptl_crystal_colour green _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.90 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_ambient_pressure 4500000(100000) _diffrn_radiation_wavelength 0.30969 _diffrn_radiation_type synchrotron _diffrn_radiation_source synchrotron _diffrn_radiation_monochromator silicon _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi scans' _diffrn_reflns_number 2864 _diffrn_reflns_av_R_equivalents 0.0889 _diffrn_reflns_av_sigmaI/netI 0.1256 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 9.90 _reflns_number_total 912 _reflns_number_gt 665 _reflns_threshold_expression >2\s(I) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. Intensities corrected for disorder solvent included in voids using the Squeeze utility P. v.d. Sluis and A. L. Spek, Acta Crystallogr., Sect A 1990, 46, 194-201 ; _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^)+(0.1366P)^2^+34.6007P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 912 _refine_ls_number_parameters 65 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1366 _refine_ls_R_factor_gt 0.1074 _refine_ls_wR_factor_ref 0.3013 _refine_ls_wR_factor_gt 0.2834 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.79188(19) 0.20260(13) 0.0793(3) 0.047(2) Uani 1 1 d . . . N1A N 0.8494(6) 0.1303(7) 0.2521(11) 0.031(3) Uiso 1 1 d G . . C2A C 0.8467(6) 0.0215(7) 0.2763(13) 0.046(5) Uiso 1 1 d G . . H2A H 0.8211 -0.0186 0.2073 0.055 Uiso 1 1 calc R . . C3A C 0.8824(7) -0.0272(5) 0.4037(14) 0.055(6) Uiso 1 1 d G . . H3A H 0.8806 -0.1000 0.4199 0.066 Uiso 1 1 calc R . . C4A C 0.9207(6) 0.0328(8) 0.5068(12) 0.033(4) Uiso 1 1 d GD . . C5A C 0.9234(6) 0.1416(8) 0.4826(13) 0.042(5) Uiso 1 1 d G . . H5A H 0.9491 0.1818 0.5516 0.050 Uiso 1 1 calc R . . C6A C 0.8877(7) 0.1903(5) 0.3553(13) 0.036(4) Uiso 1 1 d G . . H6A H 0.8895 0.2631 0.3391 0.043 Uiso 1 1 calc R . . C7A C 0.9624(6) -0.0278(10) 0.6333(16) 0.040(4) Uiso 1 1 d D . . H71A H 0.9445 -0.0736 0.6994 0.048 Uiso 1 1 calc R . . H72A H 0.9831 -0.0723 0.5738 0.048 Uiso 1 1 calc R . . C8A C 1.0000 0.0467(16) 0.7500 0.046(7) Uiso 1 2 d SD . . H81A H 0.9803 0.0915 0.8126 0.055 Uiso 0.50 1 calc PR . . H82A H 1.0197 0.0915 0.6874 0.055 Uiso 0.50 1 calc PR . . O1B O 0.8206(10) 0.2141(10) -0.1233(17) 0.056(4) Uiso 1 1 d D . . O2B O 0.7537(9) 0.2099(11) 0.2612(19) 0.069(5) Uiso 1 1 d . . . C3B C 0.7928(9) 0.2588(11) -0.2467(16) 0.024(4) Uiso 1 1 d D . . C4B C 0.8207(12) 0.2731(11) -0.395(2) 0.042(5) Uiso 1 1 d D . . H41B H 0.8108 0.2168 -0.4751 0.051 Uiso 1 1 calc R . . H42B H 0.8589 0.2720 -0.3570 0.051 Uiso 1 1 calc R . . C5B C 0.8025(12) 0.3814(9) -0.4721(18) 0.039(4) Uiso 1 1 d D . . H51B H 0.8192 0.3944 -0.5665 0.047 Uiso 1 1 calc R . . H52B H 0.7644 0.3805 -0.5120 0.047 Uiso 1 1 calc R . . C6B C 0.8172(11) 0.4710(9) -0.3441(17) 0.036(4) Uiso 1 1 d D . . H61B H 0.8553 0.4816 -0.3204 0.043 Uiso 1 1 calc R . . H62B H 0.8063 0.4521 -0.2412 0.043 Uiso 1 1 calc R . . C7B C 0.7892(8) 0.5738(9) -0.414(2) 0.031(4) Uiso 1 1 d D . . O8B O 0.7566(9) 0.0753(9) -0.0006(18) 0.049(4) Uiso 1 1 d . . . O9B O 0.8159(10) 0.3445(10) 0.1284(17) 0.053(4) 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 0.087(7) 0.0247(11) 0.0264(13) 0.0024(8) 0.000(2) 0.0068(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O8B 1.896(15) . ? Cu1 O9B 1.910(16) . ? Cu1 O2B 1.944(16) . ? Cu1 O1B 1.953(15) . ? Cu1 N1A 2.050(12) . ? Cu1 Cu1 2.580(9) 7_655 ? N1A C2A 1.3900 . ? N1A C6A 1.3900 . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C4A C5A 1.3900 . ? C4A C7A 1.540(5) . ? C5A C6A 1.3900 . ? C7A C8A 1.539(5) . ? C8A C7A 1.539(5) 2_756 ? O1B C3B 1.252(10) . ? O2B C3B 1.245(10) 7_655 ? C3B O2B 1.245(10) 7_655 ? C3B C4B 1.537(5) . ? C4B C5B 1.540(5) . ? C5B C6B 1.538(5) . ? C6B C7B 1.539(5) . ? C7B O8B 1.245(10) 4_654 ? C7B O9B 1.251(10) 6_565 ? O8B C7B 1.245(10) 4_644 ? O9B C7B 1.251(10) 6_566 ? 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 O8B Cu1 O9B 168.3(7) . . ? O8B Cu1 O2B 91.5(6) . . ? O9B Cu1 O2B 89.2(6) . . ? O8B Cu1 O1B 90.2(6) . . ? O9B Cu1 O1B 87.0(6) . . ? O2B Cu1 O1B 169.5(6) . . ? O8B Cu1 N1A 95.3(7) . . ? O9B Cu1 N1A 96.4(7) . . ? O2B Cu1 N1A 84.0(7) . . ? O1B Cu1 N1A 106.1(7) . . ? O8B Cu1 Cu1 85.6(6) . 7_655 ? O9B Cu1 Cu1 82.9(7) . 7_655 ? O2B Cu1 Cu1 82.3(6) . 7_655 ? O1B Cu1 Cu1 87.5(6) . 7_655 ? N1A Cu1 Cu1 166.3(4) . 7_655 ? C2A N1A C6A 120.0 . . ? C2A N1A Cu1 119.3(6) . . ? C6A N1A Cu1 120.5(6) . . ? C3A C2A N1A 120.0 . . ? C2A C3A C4A 120.0 . . ? C3A C4A C5A 120.0 . . ? C3A C4A C7A 117.1(8) . . ? C5A C4A C7A 122.6(9) . . ? C4A C5A C6A 120.0 . . ? C5A C6A N1A 120.0 . . ? C8A C7A C4A 112.6(9) . . ? C7A C8A C7A 104.7(14) . 2_756 ? C3B O1B Cu1 118.0(13) . . ? C3B O2B Cu1 124.4(13) 7_655 . ? O2B C3B O1B 127.2(15) 7_655 . ? O2B C3B C4B 118.6(17) 7_655 . ? O1B C3B C4B 114.2(14) . . ? C3B C4B C5B 106.2(12) . . ? C6B C5B C4B 110.9(12) . . ? C5B C6B C7B 109.3(12) . . ? O8B C7B O9B 123.6(16) 4_654 6_565 ? O8B C7B C6B 122.9(16) 4_654 . ? O9B C7B C6B 113.4(14) 6_565 . ? C7B O8B Cu1 122.8(12) 4_644 . ? C7B O9B Cu1 125.1(16) 6_566 . ? 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 C3B C4B C5B C6B 59(2) . . . . ? C4B C5B C6B C7B -169.0(17) . . . . ? _diffrn_measured_fraction_theta_max 0.489 _diffrn_reflns_theta_full 9.90 _diffrn_measured_fraction_theta_full 0.489 _refine_diff_density_max 0.569 _refine_diff_density_min -0.517 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 941417'