# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 ####################################################################### # # 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_123 _database_code_depnum_ccdc_archive 'CCDC 787501' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Ba N2 O8' _chemical_formula_weight 447.56 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' Ba Ba -0.3244 2.2819 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M Ima2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y, z' '-x+1/2, y, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1/2, z+1/2' '-x+1, y+1/2, z+1/2' _cell_length_a 17.4216(10) _cell_length_b 10.6092(6) _cell_length_c 7.4959(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1385.46(13) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.146 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 2.914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3886 _exptl_absorpt_correction_T_max 0.4752 _exptl_absorpt_process_details ? _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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4981 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1671 _reflns_number_gt 1648 _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^)+(0.0170P)^2^+0.3832P] 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(16) _refine_ls_number_reflns 1671 _refine_ls_number_parameters 117 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0156 _refine_ls_R_factor_gt 0.0152 _refine_ls_wR_factor_ref 0.0389 _refine_ls_wR_factor_gt 0.0387 _refine_ls_goodness_of_fit_ref 1.173 _refine_ls_restrained_S_all 1.172 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ba1 Ba 0.2500 1.132494(14) 0.41688(4) 0.02124(6) Uani 1 2 d S . . C1 C 0.48817(13) 0.9319(2) 0.2534(3) 0.0201(5) Uani 1 1 d . . . H1 H 0.5000 1.0000 0.2863 0.024 Uiso 1 2 d SR . . C2 C 0.53211(15) 0.8357(2) 0.1800(3) 0.0215(5) Uani 1 1 d . . . C3 C 0.50621(15) 0.7138(2) 0.1906(4) 0.0253(6) Uani 1 1 d . . . H3 H 0.5360 0.6480 0.1469 0.030 Uiso 1 1 calc R . . C4 C 0.43549(16) 0.6897(2) 0.2670(4) 0.0306(6) Uani 1 1 d . . . H4 H 0.4164 0.6078 0.2695 0.037 Uiso 1 1 calc R . . C5 C 0.39355(15) 0.7860(3) 0.3387(4) 0.0294(6) Uani 1 1 d . . . H5 H 0.3459 0.7693 0.3894 0.035 Uiso 1 1 calc R . . C6 C 0.60898(15) 0.8642(2) 0.0936(4) 0.0228(5) Uani 1 1 d . . . N1 N 0.42073(12) 0.9054(2) 0.3367(3) 0.0233(4) Uani 1 1 d . . . O1 O 0.61608(11) 0.96011(18) 0.0005(3) 0.0318(4) Uani 1 1 d . . . O2 O 0.66075(10) 0.78386(17) 0.1248(3) 0.0313(4) Uani 1 1 d . . . O3 O 0.38191(8) 0.99550(14) 0.4200(4) 0.0313(3) Uani 1 1 d . . . O1W O 0.2500 0.9204(4) 0.1588(5) 0.0469(8) Uani 1 2 d SD . . O2W O 0.2500 1.0715(4) 0.7777(5) 0.0534(9) Uani 1 2 d SD . . H1W H 0.2898(17) 0.937(4) 0.098(6) 0.076(15) Uiso 1 1 d D . . H3W H 0.2924(14) 1.059(4) 0.830(6) 0.081(16) Uiso 1 1 d 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 Ba1 0.01577(8) 0.02662(9) 0.02133(9) -0.00420(14) 0.000 0.000 C1 0.0200(11) 0.0189(12) 0.0215(11) 0.0000(9) -0.0033(9) -0.0002(8) C2 0.0225(12) 0.0215(11) 0.0204(12) 0.0009(10) -0.0025(10) 0.0056(9) C3 0.0301(14) 0.0186(12) 0.0272(13) -0.0012(10) -0.0045(11) 0.0048(8) C4 0.0375(14) 0.0232(13) 0.0311(14) 0.0034(11) -0.0025(12) -0.0041(10) C5 0.0252(13) 0.0337(14) 0.0293(13) 0.0068(11) 0.0016(11) -0.0054(10) C6 0.0191(12) 0.0276(13) 0.0218(12) -0.0056(9) -0.0008(10) 0.0032(8) N1 0.0198(10) 0.0267(10) 0.0234(10) 0.0031(9) -0.0013(8) 0.0028(8) O1 0.0262(9) 0.0356(11) 0.0336(10) 0.0060(8) 0.0045(8) 0.0043(8) O2 0.0227(9) 0.0345(12) 0.0366(12) -0.0051(8) -0.0024(8) 0.0103(6) O3 0.0240(7) 0.0340(8) 0.0358(9) -0.0031(16) 0.0083(15) 0.0093(6) O1W 0.0367(18) 0.060(2) 0.044(2) 0.0076(17) 0.000 0.000 O2W 0.0296(17) 0.095(3) 0.0358(18) 0.0254(19) 0.000 0.000 _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 Ba1 O3 2.7192(14) 4 ? Ba1 O3 2.7192(14) . ? Ba1 O2 2.7252(19) 8 ? Ba1 O2 2.7252(19) 5_455 ? Ba1 O2W 2.781(4) . ? Ba1 O2 2.828(2) 3_475 ? Ba1 O2 2.828(2) 2_675 ? Ba1 O1W 2.968(4) . ? Ba1 O2W 3.309(5) 6_574 ? C1 N1 1.360(3) . ? C1 C2 1.389(3) . ? C1 C1 1.503(4) 2_675 ? C1 H1 0.7911 . ? C2 C3 1.371(4) . ? C2 C6 1.518(4) . ? C3 C4 1.382(4) . ? C3 H3 0.9300 . ? C4 C5 1.367(4) . ? C4 H4 0.9300 . ? C5 N1 1.352(4) . ? C5 H5 0.9300 . ? C6 O1 1.240(3) . ? C6 O2 1.263(3) . ? N1 O3 1.327(3) . ? O2 Ba1 2.7252(18) 5_544 ? O2 Ba1 2.828(2) 2_675 ? O1W H1W 0.847(10) . ? O2W Ba1 3.309(5) 6_575 ? O2W H3W 0.847(10) . ? 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 Ba1 O3 115.37(7) 4 . ? O3 Ba1 O2 142.40(8) 4 8 ? O3 Ba1 O2 80.09(6) . 8 ? O3 Ba1 O2 80.09(6) 4 5_455 ? O3 Ba1 O2 142.40(8) . 5_455 ? O2 Ba1 O2 69.58(8) 8 5_455 ? O3 Ba1 O2W 82.38(8) 4 . ? O3 Ba1 O2W 82.38(8) . . ? O2 Ba1 O2W 65.22(8) 8 . ? O2 Ba1 O2W 65.22(8) 5_455 . ? O3 Ba1 O2 73.12(7) 4 3_475 ? O3 Ba1 O2 129.72(8) . 3_475 ? O2 Ba1 O2 124.86(3) 8 3_475 ? O2 Ba1 O2 86.80(4) 5_455 3_475 ? O2W Ba1 O2 145.68(4) . 3_475 ? O3 Ba1 O2 129.72(8) 4 2_675 ? O3 Ba1 O2 73.12(7) . 2_675 ? O2 Ba1 O2 86.80(4) 8 2_675 ? O2 Ba1 O2 124.86(3) 5_455 2_675 ? O2W Ba1 O2 145.68(4) . 2_675 ? O2 Ba1 O2 66.71(7) 3_475 2_675 ? O3 Ba1 O1W 66.44(6) 4 . ? O3 Ba1 O1W 66.44(6) . . ? O2 Ba1 O1W 145.06(4) 8 . ? O2 Ba1 O1W 145.06(4) 5_455 . ? O2W Ba1 O1W 117.23(12) . . ? O2 Ba1 O1W 74.53(7) 3_475 . ? O2 Ba1 O1W 74.53(7) 2_675 . ? O3 Ba1 O2W 120.66(4) 4 6_574 ? O3 Ba1 O2W 120.66(4) . 6_574 ? O2 Ba1 O2W 67.73(6) 8 6_574 ? O2 Ba1 O2W 67.73(6) 5_455 6_574 ? O2W Ba1 O2W 121.83(11) . 6_574 ? O2 Ba1 O2W 57.19(6) 3_475 6_574 ? O2 Ba1 O2W 57.19(6) 2_675 6_574 ? O1W Ba1 O2W 120.94(9) . 6_574 ? O3 Ba1 Ba1 106.80(6) 4 6_575 ? O3 Ba1 Ba1 106.80(6) . 6_575 ? O2 Ba1 Ba1 36.62(4) 8 6_575 ? O2 Ba1 Ba1 36.62(4) 5_455 6_575 ? O2W Ba1 Ba1 47.09(9) . 6_575 ? O2 Ba1 Ba1 118.08(4) 3_475 6_575 ? O2 Ba1 Ba1 118.08(4) 2_675 6_575 ? O1W Ba1 Ba1 164.32(7) . 6_575 ? O2W Ba1 Ba1 74.74(6) 6_574 6_575 ? O3 Ba1 Ba1 107.64(6) 4 6_574 ? O3 Ba1 Ba1 107.64(6) . 6_574 ? O2 Ba1 Ba1 98.62(4) 8 6_574 ? O2 Ba1 Ba1 98.62(4) 5_455 6_574 ? O2W Ba1 Ba1 159.82(10) . 6_574 ? O2 Ba1 Ba1 35.08(4) 3_475 6_574 ? O2 Ba1 Ba1 35.08(4) 2_675 6_574 ? O1W Ba1 Ba1 82.95(7) . 6_574 ? O2W Ba1 Ba1 37.99(6) 6_574 6_574 ? Ba1 Ba1 Ba1 112.733(8) 6_575 6_574 ? N1 C1 C2 120.4(2) . . ? N1 C1 C1 115.8(2) . 2_675 ? C2 C1 C1 123.7(3) . 2_675 ? N1 C1 H1 105.7 . . ? C2 C1 H1 130.6 . . ? C1 C1 H1 18.2 2_675 . ? C3 C2 C1 119.2(2) . . ? C3 C2 C6 120.2(2) . . ? C1 C2 C6 120.6(2) . . ? C2 C3 C4 119.5(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? N1 C5 C4 120.6(2) . . ? N1 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? O1 C6 O2 125.9(3) . . ? O1 C6 C2 119.5(2) . . ? O2 C6 C2 114.6(2) . . ? O3 N1 C5 119.4(2) . . ? O3 N1 C1 120.5(2) . . ? C5 N1 C1 120.1(2) . . ? C6 O2 Ba1 134.36(18) . 5_544 ? C6 O2 Ba1 108.93(16) . 2_675 ? Ba1 O2 Ba1 108.30(6) 5_544 2_675 ? N1 O3 Ba1 144.26(19) . . ? Ba1 O1W H1W 101(3) . . ? Ba1 O2W Ba1 94.92(11) . 6_575 ? Ba1 O2W H3W 119(3) . . ? Ba1 O2W H3W 90(3) 6_575 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.783 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.067 data_Cu _database_code_depnum_ccdc_archive 'CCDC 787502' #============================================================================= _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu N2 O7' _chemical_formula_weight 355.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I4(1)/acd loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+1/4, x+3/4, z+1/4' 'y+1/4, -x+1/4, z+3/4' '-x+1/2, y, -z' 'x, -y, -z+1/2' 'y+1/4, x+3/4, -z+3/4' '-y+1/4, -x+1/4, -z+1/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+3/4, x+5/4, z+3/4' 'y+3/4, -x+3/4, z+5/4' '-x+1, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1' 'y+3/4, x+5/4, -z+5/4' '-y+3/4, -x+3/4, -z+3/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-1/4, -x-3/4, -z-1/4' '-y-1/4, x-1/4, -z-3/4' 'x-1/2, -y, z' '-x, y, z-1/2' '-y-1/4, -x-3/4, z-3/4' 'y-1/4, x-1/4, z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y+1/4, -x-1/4, -z+1/4' '-y+1/4, x+1/4, -z-1/4' 'x, -y+1/2, z+1/2' '-x+1/2, y+1/2, z' '-y+1/4, -x-1/4, z-1/4' 'y+1/4, x+1/4, z+1/4' _cell_length_a 13.831(2) _cell_length_b 13.831(2) _cell_length_c 27.458(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5252.4(19) _cell_formula_units_Z 16 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.799 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2864 _exptl_absorpt_coefficient_mu 1.703 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5146 _exptl_absorpt_correction_T_max 0.8090 _exptl_absorpt_process_details ? _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 ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16705 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 26.96 _reflns_number_total 1435 _reflns_number_gt 1073 _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^)+(0.0617P)^2^+15.1334P] 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 1435 _refine_ls_number_parameters 101 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1102 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.163 _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 0.16097(3) 1.08903(3) 0.1250 0.0289(2) Uani 1 2 d S . . O3 O 0.3024(2) 1.08847(17) 0.11696(11) 0.0368(7) Uani 1 1 d . . . C6 C 0.3382(2) 0.9280(3) 0.09852(13) 0.0255(7) Uani 1 1 d . . . N1 N 0.3321(2) 1.0211(2) 0.08409(11) 0.0305(7) Uani 1 1 d . . . C5 C 0.3581(3) 0.8566(3) 0.06403(13) 0.0297(8) Uani 1 1 d . . . C4 C 0.3795(3) 0.8849(3) 0.01682(15) 0.0399(9) Uani 1 1 d . . . H4A H 0.3940 0.8386 -0.0067 0.048 Uiso 1 1 calc R . . C3 C 0.3531(3) 1.0493(3) 0.03843(16) 0.0405(10) Uani 1 1 d . . . H3A H 0.3499 1.1143 0.0299 0.049 Uiso 1 1 calc R . . C2 C 0.3793(3) 0.9814(3) 0.00464(16) 0.0460(11) Uani 1 1 d . . . H2A H 0.3969 1.0005 -0.0266 0.055 Uiso 1 1 calc R . . C1 C 0.3535(3) 0.7501(3) 0.07630(14) 0.0340(8) Uani 1 1 d . . . O2 O 0.33627(19) 0.72879(19) 0.12061(9) 0.0350(6) Uani 1 1 d . . . O1 O 0.3657(3) 0.6908(2) 0.04386(12) 0.0592(10) Uani 1 1 d . . . O1W O 0.5000 0.7500 0.9067(5) 0.53(3) Uani 1 2 d SD . . H1W H 0.4391 0.7553 0.9018 0.790 Uiso 0.50 1 d PRD . . H2W H 0.5130 0.8094 0.9121 0.790 Uiso 0.50 1 d PRD . . 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 0.0248(3) 0.0248(3) 0.0371(4) 0.00030(18) 0.00030(18) 0.0031(2) O3 0.0291(14) 0.0244(14) 0.0569(18) -0.0016(12) 0.0061(13) 0.0004(11) C6 0.0228(17) 0.0243(17) 0.0292(19) 0.0045(13) -0.0013(14) -0.0017(13) N1 0.0270(16) 0.0261(16) 0.0384(17) 0.0035(13) 0.0003(13) 0.0015(12) C5 0.0268(18) 0.031(2) 0.0310(19) 0.0008(15) -0.0004(14) 0.0008(15) C4 0.041(2) 0.048(3) 0.0301(19) 0.0014(18) 0.0018(17) 0.0045(19) C3 0.034(2) 0.040(2) 0.048(2) 0.019(2) 0.0024(18) 0.0012(18) C2 0.042(2) 0.061(3) 0.035(2) 0.018(2) 0.0053(19) 0.003(2) C1 0.036(2) 0.029(2) 0.037(2) -0.0055(17) -0.0063(16) -0.0013(16) O2 0.0435(17) 0.0234(13) 0.0382(15) -0.0016(11) 0.0028(12) -0.0043(11) O1 0.097(3) 0.0375(18) 0.0431(18) -0.0146(14) -0.0015(17) 0.0083(18) O1W 1.04(7) 0.41(3) 0.123(11) 0.000 0.000 -0.31(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 Cu1 O2 1.937(3) 20_666 ? Cu1 O2 1.937(3) 30 ? Cu1 O3 1.969(3) . ? Cu1 O3 1.969(3) 8_665 ? O3 N1 1.361(4) . ? C6 N1 1.350(4) . ? C6 C5 1.395(5) . ? C6 C6 1.489(7) 8_665 ? N1 C3 1.345(5) . ? C5 C4 1.386(6) . ? C5 C1 1.512(5) . ? C4 C2 1.376(6) . ? C4 H4A 0.9300 . ? C3 C2 1.369(6) . ? C3 H3A 0.9300 . ? C2 H2A 0.9300 . ? C1 O1 1.223(5) . ? C1 O2 1.274(4) . ? O2 Cu1 1.937(3) 27_465 ? O1W O1W 1.74(3) 19_577 ? O1W H1W 0.8566 . ? O1W H2W 0.8538 . ? 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 O2 Cu1 O2 92.48(16) 20_666 30 ? O2 Cu1 O3 176.82(11) 20_666 . ? O2 Cu1 O3 88.70(10) 30 . ? O2 Cu1 O3 88.70(10) 20_666 8_665 ? O2 Cu1 O3 176.83(12) 30 8_665 ? O3 Cu1 O3 90.27(14) . 8_665 ? N1 O3 Cu1 112.1(2) . . ? N1 C6 C5 119.2(3) . . ? N1 C6 C6 114.9(3) . 8_665 ? C5 C6 C6 125.9(3) . 8_665 ? C3 N1 C6 122.5(3) . . ? C3 N1 O3 119.0(3) . . ? C6 N1 O3 118.5(3) . . ? C4 C5 C6 118.5(4) . . ? C4 C5 C1 119.5(4) . . ? C6 C5 C1 122.0(3) . . ? C2 C4 C5 120.0(4) . . ? C2 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? N1 C3 C2 119.3(4) . . ? N1 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C4 C2 C3 120.1(4) . . ? C4 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? O1 C1 O2 124.5(4) . . ? O1 C1 C5 119.0(4) . . ? O2 C1 C5 116.5(3) . . ? C1 O2 Cu1 106.6(2) . 27_465 ? O1W O1W H1W 80.9 19_577 . ? O1W O1W H2W 99.9 19_577 . ? H1W O1W H2W 98.8 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.96 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.899 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.081