# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Tapas Maji' _publ_contact_author_email TMAJI@JNCASR.AC.IN loop_ _publ_author_name T.Maji K.L.Gurunatha P.Kanoo data_compound1 _database_code_depnum_ccdc_archive 'CCDC 744617' #TrackingRef 'CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H6 Cu O8' _chemical_formula_weight 341.71 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' 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 P42/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-y, x+1/2, z+1/2' 'y+1/2, -x, z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'y, -x-1/2, -z-1/2' '-y-1/2, x, -z-1/2' _cell_length_a 20.539(2) _cell_length_b 20.539(2) _cell_length_c 6.9994(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2952.7(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 25.8 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 1.512 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8678 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 59735 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 25.84 _reflns_number_total 2851 _reflns_number_gt 2579 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4.1' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.0638P)^2^+5.5254P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2851 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1016 _refine_ls_goodness_of_fit_ref 1.139 _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 C1 C 0.81400(13) 0.01568(13) 0.6776(4) 0.0128(6) Uani 1 1 d . . . C2 C 0.79628(14) -0.00976(15) 0.8507(4) 0.0177(6) Uani 1 1 d . . . H2 H 0.8283 -0.0280 0.9328 0.021 Uiso 1 1 calc R . . C3 C 0.73034(13) -0.00884(14) 0.9065(4) 0.0175(6) Uani 1 1 d . . . H3 H 0.7181 -0.0282 1.0244 0.021 Uiso 1 1 calc R . . C4 C 0.68323(13) 0.01958(13) 0.7939(4) 0.0122(5) Uani 1 1 d . . . C5 C 0.65772(13) 0.08979(14) 0.5065(4) 0.0169(6) Uani 1 1 d . . . H5 H 0.6133 0.0930 0.5435 0.020 Uiso 1 1 calc R . . C6 C 0.67831(15) 0.12122(17) 0.3457(5) 0.0239(7) Uani 1 1 d . . . H6 H 0.6482 0.1460 0.2728 0.029 Uiso 1 1 calc R . . C7 C 0.74390(15) 0.11735(17) 0.2863(5) 0.0250(7) Uani 1 1 d . . . H7 H 0.7577 0.1394 0.1741 0.030 Uiso 1 1 calc R . . C8 C 0.78736(14) 0.08191(15) 0.3904(4) 0.0191(6) Uani 1 1 d . . . H8 H 0.8313 0.0791 0.3490 0.023 Uiso 1 1 calc R . . C9 C 0.76798(13) 0.04902(13) 0.5601(4) 0.0129(5) Uani 1 1 d . . . C10 C 0.70121(13) 0.05233(13) 0.6200(4) 0.0120(5) Uani 1 1 d . . . C11 C 0.88381(13) 0.00810(12) 0.6169(4) 0.0119(5) Uani 1 1 d . . . C12 C 0.61429(13) 0.01263(13) 0.8652(4) 0.0112(5) Uani 1 1 d . . . O1 O 0.89410(9) -0.01488(10) 0.4516(3) 0.0160(4) Uani 1 1 d . . . O2 O 0.92656(9) 0.02481(10) 0.7345(3) 0.0155(4) Uani 1 1 d . . . O1W O 0.87697(12) -0.18228(12) 0.0794(4) 0.0326(6) Uiso 1 1 d . . . O3 O 0.56749(9) 0.02382(10) 0.7508(3) 0.0148(4) Uani 1 1 d . . . O2WA O 0.8130(3) -0.1186(3) 0.3660(8) 0.0355(12) Uiso 0.50 1 d P . . O2WB O 0.7984(2) -0.0967(2) 0.2836(7) 0.0288(10) Uiso 0.50 1 d P . . O4 O 0.60741(9) -0.00537(10) 1.0347(3) 0.0176(4) Uani 1 1 d . . . O3WA O 0.8464(4) -0.1914(4) -0.0992(13) 0.075(2) Uiso 0.50 1 d P . . O3WB O 0.8161(3) -0.1821(3) -0.2751(9) 0.0474(14) Uiso 0.50 1 d P . . O5 O 0.94535(9) -0.06851(9) 0.0830(3) 0.0153(4) Uani 1 1 d . . . Cu1 Cu 0.981028(15) -0.023909(15) 0.33626(4) 0.00805(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0102(13) 0.0125(13) 0.0156(14) -0.0011(10) 0.0023(10) -0.0009(10) C2 0.0120(14) 0.0228(15) 0.0183(15) 0.0052(11) 0.0015(11) 0.0043(11) C3 0.0124(13) 0.0241(15) 0.0161(14) 0.0050(12) 0.0035(11) 0.0018(11) C4 0.0088(12) 0.0141(13) 0.0138(13) -0.0023(11) 0.0023(10) -0.0007(10) C5 0.0098(13) 0.0196(14) 0.0214(15) 0.0033(11) 0.0003(11) -0.0001(11) C6 0.0154(15) 0.0302(17) 0.0261(17) 0.0123(13) -0.0017(12) 0.0029(13) C7 0.0187(15) 0.0342(18) 0.0223(15) 0.0138(14) 0.0033(13) -0.0011(13) C8 0.0112(13) 0.0260(15) 0.0202(15) 0.0053(12) 0.0041(11) -0.0003(11) C9 0.0111(13) 0.0124(13) 0.0154(13) -0.0007(10) 0.0021(10) -0.0014(10) C10 0.0111(13) 0.0110(12) 0.0139(13) -0.0023(10) 0.0000(10) -0.0018(10) C11 0.0118(13) 0.0082(12) 0.0156(13) 0.0046(10) 0.0017(11) 0.0005(9) C12 0.0104(13) 0.0100(12) 0.0132(13) -0.0030(10) 0.0025(10) -0.0011(10) O1 0.0092(9) 0.0224(10) 0.0162(10) -0.0038(8) 0.0035(7) -0.0010(8) O2 0.0078(9) 0.0237(10) 0.0150(10) -0.0009(8) 0.0017(8) 0.0014(8) O3 0.0070(9) 0.0231(10) 0.0143(10) 0.0024(8) 0.0020(7) -0.0006(7) O4 0.0097(9) 0.0285(11) 0.0146(10) 0.0035(8) 0.0027(8) -0.0014(8) O5 0.0178(10) 0.0159(9) 0.0122(10) -0.0002(8) 0.0008(8) -0.0020(8) Cu1 0.00738(19) 0.00711(19) 0.0097(2) 0.00172(11) 0.00163(11) 0.00051(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 C2 1.369(4) . ? C1 C9 1.428(4) . ? C1 C11 1.503(4) . ? C2 C3 1.410(4) . ? C3 C4 1.378(4) . ? C4 C10 1.439(4) . ? C4 C12 1.508(4) . ? C5 C6 1.365(4) . ? C5 C10 1.422(4) . ? C6 C7 1.412(4) . ? C7 C8 1.363(4) . ? C8 C9 1.423(4) . ? C9 C10 1.436(4) . ? C11 O2 1.251(3) . ? C11 O1 1.267(3) . ? C12 O4 1.251(3) . ? C12 O3 1.272(3) . ? O1 Cu1 1.9683(19) . ? O2 Cu1 1.9617(19) 5_756 ? O1W O3WA 1.412(9) . ? O3 Cu1 1.9727(18) 4_565 ? O2WA O2WB 0.791(6) . ? O4 Cu1 1.9583(19) 8_647 ? O3WA O3WB 1.393(10) . ? O5 Cu1 2.126(2) . ? Cu1 O4 1.9583(19) 7_667 ? Cu1 O2 1.9617(19) 5_756 ? Cu1 O3 1.9727(18) 3_644 ? Cu1 Cu1 2.6127(7) 5_756 ? 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 C2 C1 C9 121.1(3) . . ? C2 C1 C11 117.6(2) . . ? C9 C1 C11 121.2(2) . . ? C1 C2 C3 119.7(3) . . ? C4 C3 C2 121.4(3) . . ? C3 C4 C10 120.1(2) . . ? C3 C4 C12 115.4(2) . . ? C10 C4 C12 124.4(2) . . ? C6 C5 C10 121.5(3) . . ? C5 C6 C7 120.8(3) . . ? C8 C7 C6 119.8(3) . . ? C7 C8 C9 121.1(3) . . ? C8 C9 C1 121.5(2) . . ? C8 C9 C10 119.2(2) . . ? C1 C9 C10 119.1(2) . . ? C5 C10 C9 117.5(2) . . ? C5 C10 C4 124.4(2) . . ? C9 C10 C4 118.0(2) . . ? O2 C11 O1 125.8(2) . . ? O2 C11 C1 117.1(2) . . ? O1 C11 C1 117.1(2) . . ? O4 C12 O3 124.4(2) . . ? O4 C12 C4 116.6(2) . . ? O3 C12 C4 118.9(2) . . ? C11 O1 Cu1 124.12(18) . . ? C11 O2 Cu1 120.67(18) . 5_756 ? C12 O3 Cu1 121.26(17) . 4_565 ? C12 O4 Cu1 125.34(18) . 8_647 ? O3WB O3WA O1W 164.5(7) . . ? O4 Cu1 O2 88.29(9) 7_667 5_756 ? O4 Cu1 O1 91.31(9) 7_667 . ? O2 Cu1 O1 169.16(8) 5_756 . ? O4 Cu1 O3 168.65(8) 7_667 3_644 ? O2 Cu1 O3 88.92(8) 5_756 3_644 ? O1 Cu1 O3 89.37(8) . 3_644 ? O4 Cu1 O5 93.23(8) 7_667 . ? O2 Cu1 O5 96.82(8) 5_756 . ? O1 Cu1 O5 94.02(8) . . ? O3 Cu1 O5 98.03(8) 3_644 . ? O4 Cu1 Cu1 83.23(6) 7_667 5_756 ? O2 Cu1 Cu1 86.36(6) 5_756 5_756 ? O1 Cu1 Cu1 82.83(6) . 5_756 ? O3 Cu1 Cu1 85.61(6) 3_644 5_756 ? O5 Cu1 Cu1 175.18(6) . 5_756 ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.84 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.805 _refine_diff_density_min -0.815 _refine_diff_density_rms 0.278 #===END data_compound2 _database_code_depnum_ccdc_archive 'CCDC 744618' #TrackingRef 'CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cu O6' _chemical_formula_weight 341.79 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' 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 Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 16.1983(8) _cell_length_b 14.3762(8) _cell_length_c 12.8497(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2992.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 25.8 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 1.482 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8824 _exptl_absorpt_correction_T_max 0.9913 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _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 18121 _diffrn_reflns_av_R_equivalents 0.0713 _diffrn_reflns_av_sigmaI/netI 0.0695 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.84 _reflns_number_total 2856 _reflns_number_gt 1646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4.1' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.1060P)^2^+24.6623P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2856 _refine_ls_number_parameters 187 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1255 _refine_ls_R_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.2341 _refine_ls_wR_factor_gt 0.1787 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.1784(5) 0.3871(5) 0.7372(6) 0.0201(17) Uani 1 1 d . . . C2 C 0.2448(4) 0.3722(5) 0.7996(7) 0.0256(18) Uani 1 1 d . . . H2 H 0.2458 0.3190 0.8434 0.031 Uiso 1 1 calc R . . C3 C 0.3112(5) 0.4334(5) 0.8004(7) 0.0265(18) Uani 1 1 d . . . H3 H 0.3566 0.4218 0.8455 0.032 Uiso 1 1 calc R . . C4 C 0.3124(4) 0.5103(5) 0.7372(6) 0.0203(17) Uani 1 1 d . . . C5 C 0.2388(5) 0.6123(6) 0.6105(6) 0.0268(19) Uani 1 1 d . . . H5 H 0.2845 0.6537 0.6089 0.032 Uiso 1 1 calc R . . C6 C 0.1687(5) 0.6336(6) 0.5555(7) 0.034(2) Uani 1 1 d . . . H6 H 0.1666 0.6893 0.5159 0.041 Uiso 1 1 calc R . . C7 C 0.0997(5) 0.5735(7) 0.5572(7) 0.039(2) Uani 1 1 d . . . H7 H 0.0512 0.5890 0.5193 0.047 Uiso 1 1 calc R . . C8 C 0.1030(4) 0.4929(6) 0.6134(7) 0.029(2) Uani 1 1 d . . . H8 H 0.0565 0.4526 0.6141 0.035 Uiso 1 1 calc R . . C9 C 0.1753(4) 0.4681(5) 0.6714(6) 0.0214(17) Uani 1 1 d . . . C10 C 0.2437(4) 0.5303(5) 0.6692(6) 0.0202(17) Uani 1 1 d . . . C11 C 0.1103(4) 0.3173(5) 0.7406(6) 0.0217(18) Uani 1 1 d . . . C12 C 0.3858(4) 0.5746(5) 0.7405(6) 0.0183(16) Uani 1 1 d . . . C13 C -0.0438(8) 0.1227(10) 0.4214(9) 0.081(4) Uani 1 1 d . . . H13A H -0.0013 0.0745 0.4147 0.122 Uiso 1 1 calc R . . H13B H -0.0584 0.1461 0.3522 0.122 Uiso 1 1 calc R . . H13C H -0.0929 0.0962 0.4546 0.122 Uiso 1 1 calc R . . C14 C 0.1476(12) 0.3610(13) 0.3728(14) 0.128(6) Uiso 1 1 d . . . H14A H 0.1207 0.4174 0.3989 0.192 Uiso 1 1 calc R . . H14B H 0.1269 0.3468 0.3029 0.192 Uiso 1 1 calc R . . H14C H 0.2074 0.3708 0.3699 0.192 Uiso 1 1 calc R . . O1 O 0.0817(3) 0.2884(3) 0.6534(4) 0.0221(12) Uani 1 1 d . . . O2 O 0.0871(3) 0.2895(4) 0.8282(4) 0.0247(13) Uani 1 1 d . . . O3 O 0.4187(3) 0.5976(4) 0.6568(4) 0.0219(12) Uani 1 1 d . . . O4 O 0.4086(3) 0.5995(4) 0.8304(4) 0.0245(13) Uani 1 1 d . . . O5 O -0.0134(4) 0.1960(4) 0.4824(4) 0.0326(14) Uani 1 1 d D . . O6 O 0.1299(6) 0.2856(7) 0.4404(8) 0.087(3) Uiso 1 1 d . . . H6A H 0.1632 0.2860 0.4904 0.131 Uiso 1 1 calc R . . Cu1 Cu -0.00520(5) 0.19232(6) 0.64825(6) 0.0143(3) Uani 1 1 d . . . H5A H 0.025(7) 0.234(8) 0.445(10) 0.12(5) 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 C1 0.025(4) 0.016(4) 0.019(4) 0.002(3) 0.002(3) -0.001(3) C2 0.021(4) 0.026(4) 0.030(4) 0.011(4) -0.005(4) -0.003(3) C3 0.025(4) 0.025(4) 0.030(5) 0.009(4) -0.008(4) -0.003(3) C4 0.013(3) 0.022(4) 0.026(4) 0.001(4) 0.001(3) -0.002(3) C5 0.021(4) 0.032(5) 0.027(4) 0.010(4) 0.001(3) -0.008(3) C6 0.037(5) 0.030(5) 0.034(5) 0.017(4) -0.005(4) -0.005(4) C7 0.024(4) 0.050(6) 0.044(6) 0.014(5) -0.018(4) 0.002(4) C8 0.016(3) 0.029(5) 0.043(5) 0.006(4) -0.009(4) -0.004(3) C9 0.017(4) 0.025(4) 0.023(4) 0.001(3) -0.002(3) 0.002(3) C10 0.022(4) 0.019(4) 0.020(4) -0.002(3) 0.004(3) 0.000(3) C11 0.013(3) 0.018(4) 0.034(5) 0.001(4) -0.007(3) 0.003(3) C12 0.012(3) 0.015(3) 0.029(5) -0.005(4) -0.004(3) 0.000(3) C13 0.093(9) 0.112(11) 0.039(7) -0.038(7) 0.018(6) -0.053(9) O1 0.021(3) 0.023(3) 0.022(3) 0.001(2) 0.000(2) -0.009(2) O2 0.023(3) 0.028(3) 0.023(3) 0.000(2) 0.001(2) -0.012(2) O3 0.022(3) 0.025(3) 0.019(3) -0.002(2) 0.002(2) -0.006(2) O4 0.021(3) 0.029(3) 0.023(3) 0.002(2) -0.003(2) -0.010(2) O5 0.043(3) 0.036(3) 0.019(3) 0.001(3) -0.006(3) -0.005(3) Cu1 0.0126(5) 0.0147(5) 0.0155(5) 0.0001(4) 0.0004(4) 0.0001(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 C2 1.358(11) . ? C1 C9 1.440(10) . ? C1 C11 1.492(10) . ? C2 C3 1.391(10) . ? C3 C4 1.372(11) . ? C4 C10 1.443(10) . ? C4 C12 1.507(9) . ? C5 C6 1.372(11) . ? C5 C10 1.402(11) . ? C6 C7 1.414(11) . ? C7 C8 1.366(11) . ? C8 C9 1.434(10) . ? C9 C10 1.424(10) . ? C11 O2 1.253(9) . ? C11 O1 1.282(9) . ? C12 O3 1.246(9) . ? C12 O4 1.265(8) . ? C13 O5 1.402(12) . ? C14 O6 1.418(18) . ? O1 Cu1 1.973(5) . ? O2 Cu1 1.949(5) 4_556 ? O3 Cu1 1.957(5) 7_665 ? O4 Cu1 1.951(5) 6_667 ? O5 Cu1 2.136(6) . ? Cu1 O2 1.949(5) 4_556 ? Cu1 O4 1.951(5) 6_557 ? Cu1 O3 1.957(5) 7_655 ? Cu1 Cu1 2.6202(17) 4_556 ? 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 C2 C1 C9 120.1(7) . . ? C2 C1 C11 117.5(7) . . ? C9 C1 C11 122.4(7) . . ? C1 C2 C3 121.2(7) . . ? C4 C3 C2 121.0(7) . . ? C3 C4 C10 120.6(7) . . ? C3 C4 C12 119.2(7) . . ? C10 C4 C12 120.2(7) . . ? C6 C5 C10 120.8(7) . . ? C5 C6 C7 120.7(8) . . ? C8 C7 C6 119.7(7) . . ? C7 C8 C9 121.2(7) . . ? C10 C9 C8 118.0(7) . . ? C10 C9 C1 119.5(6) . . ? C8 C9 C1 122.3(7) . . ? C5 C10 C9 119.6(7) . . ? C5 C10 C4 122.5(7) . . ? C9 C10 C4 117.5(7) . . ? O2 C11 O1 125.0(7) . . ? O2 C11 C1 117.6(7) . . ? O1 C11 C1 117.4(7) . . ? O3 C12 O4 126.0(6) . . ? O3 C12 C4 118.5(7) . . ? O4 C12 C4 115.5(7) . . ? C11 O1 Cu1 120.9(5) . . ? C11 O2 Cu1 125.0(5) . 4_556 ? C12 O3 Cu1 122.7(5) . 7_665 ? C12 O4 Cu1 122.1(5) . 6_667 ? C13 O5 Cu1 124.1(6) . . ? O2 Cu1 O4 88.9(2) 4_556 6_557 ? O2 Cu1 O3 167.7(2) 4_556 7_655 ? O4 Cu1 O3 91.6(2) 6_557 7_655 ? O2 Cu1 O1 88.8(2) 4_556 . ? O4 Cu1 O1 170.0(2) 6_557 . ? O3 Cu1 O1 88.6(2) 7_655 . ? O2 Cu1 O5 95.5(2) 4_556 . ? O4 Cu1 O5 96.5(2) 6_557 . ? O3 Cu1 O5 96.7(2) 7_655 . ? O1 Cu1 O5 93.5(2) . . ? O2 Cu1 Cu1 83.62(16) 4_556 4_556 ? O4 Cu1 Cu1 84.60(16) 6_557 4_556 ? O3 Cu1 Cu1 84.15(15) 7_655 4_556 ? O1 Cu1 Cu1 85.46(15) . 4_556 ? O5 Cu1 Cu1 178.58(16) . 4_556 ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.84 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.464 _refine_diff_density_min -1.134 _refine_diff_density_rms 0.167 #===END data_compound3 _database_code_depnum_ccdc_archive 'CCDC 744619' #TrackingRef 'CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H4 Cu O5, 1(O), 0.8(O)' _chemical_formula_sum 'C12 H4 Cu O6.80' _chemical_formula_weight 320.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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 Tetragonal _symmetry_space_group_name_Hall '-I 4 2' _symmetry_space_group_name_H-M 'I 4/m m m' _symmetry_Int_Tables_number 139 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z' '-x, -y, z' 'y, -x, z' 'x, -y, -z' 'y, x, -z' '-x, y, -z' '-y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' 'y+1/2, x+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-y+1/2, -x+1/2, -z+1/2' '-x, -y, -z' 'y, -x, -z' 'x, y, -z' '-y, x, -z' '-x, y, z' '-y, -x, z' 'x, -y, z' 'y, x, z' '-x+1/2, -y+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' '-x+1/2, y+1/2, z+1/2' '-y+1/2, -x+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 10.8058(6) _cell_length_b 10.8058(6) _cell_length_c 14.2168(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1660.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 638 _exptl_absorpt_coefficient_mu 1.335 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8418 _exptl_absorpt_correction_T_max 0.9122 _exptl_absorpt_process_details SADABS _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 ? _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 7515 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.53 _reflns_number_total 579 _reflns_number_gt 531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker,2000)' _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Mercury 1.4.1' _computing_publication_material 'PLATON (Spek, 2003)' _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^)+(0.1574P)^2^+19.2699P] 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 noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.013(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 579 _refine_ls_number_parameters 57 _refine_ls_number_restraints 43 _refine_ls_R_factor_all 0.0910 _refine_ls_R_factor_gt 0.0861 _refine_ls_wR_factor_ref 0.2715 _refine_ls_wR_factor_gt 0.2679 _refine_ls_goodness_of_fit_ref 1.199 _refine_ls_restrained_S_all 1.159 _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 0.5000 0.5000 0.40784(11) 0.0225(8) Uani 1 8 d S . . O1 O 0.5000 0.6785(6) 0.4215(4) 0.049(2) Uani 1 2 d SU . . O1W O 0.5000 0.5000 0.2601(10) 0.059(4) Uani 1 8 d S . . C1 C 0.5000 0.7330(11) 0.5000 0.026(2) Uani 1 4 d SU . . C2 C 0.5000 0.8711(10) 0.5000 0.025(2) Uani 1 4 d SU . . C3 C 0.4318(13) 0.9354(12) 0.4316(8) 0.034(3) Uani 0.50 1 d PU . . C4 C 0.349(3) 0.871(2) 0.3684(15) 0.036(5) Uani 0.25 1 d PU . . H4 H 0.3514 0.7848 0.3652 0.043 Uiso 0.25 1 calc PR . . C5 C 0.266(3) 0.9360(9) 0.3123(19) 0.048(7) Uani 0.25 1 d PDU . . H5 H 0.2098 0.8932 0.2746 0.058 Uiso 0.25 1 calc PR . . O2W O 0.138(6) 1.138(6) 0.5000 0.2499(18) Uani 0.50 4 d SPU . . O3W O 0.2500 0.2500 0.2500 0.2600(18) Uani 0.40 4 d SPU . . 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 0.0270(9) 0.0270(9) 0.0135(10) 0.000 0.000 0.000 O1 0.094(6) 0.025(3) 0.027(3) 0.002(2) 0.000 0.000 O1W 0.078(7) 0.078(7) 0.021(6) 0.000 0.000 0.000 C1 0.017(4) 0.032(5) 0.029(5) 0.000 0.000 0.000 C2 0.029(5) 0.025(5) 0.022(5) 0.000 0.000 0.000 C3 0.050(7) 0.033(6) 0.019(4) -0.002(5) -0.009(5) -0.001(5) C4 0.058(14) 0.031(10) 0.019(9) -0.011(8) -0.015(9) 0.001(10) C5 0.081(19) 0.026(12) 0.038(12) 0.003(9) -0.031(13) 0.013(12) O2W 0.2499(18) 0.2499(18) 0.250(2) 0.000 0.000 0.0000(10) O3W 0.2600(18) 0.2600(18) 0.260(2) 0.0000(7) 0.0000(7) 0.0000(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 Cu1 O1 1.938(7) 2_655 ? Cu1 O1 1.938(7) . ? Cu1 O1 1.938(7) 4_565 ? Cu1 O1 1.938(7) 3_665 ? Cu1 O1W 2.101(14) . ? Cu1 Cu1 2.620(3) 17_666 ? O1 C1 1.262(8) . ? C1 O1 1.262(8) 19_556 ? C1 C2 1.492(16) . ? C2 C3 1.404(13) 7_656 ? C2 C3 1.404(13) 19_556 ? C2 C3 1.404(13) . ? C2 C3 1.404(13) 21_655 ? C3 C3 1.40(3) 23_575 ? C3 C4 1.45(2) . ? C4 C5 1.39(3) . ? C4 H4 0.9300 . ? C5 C5 1.383(19) 23_575 ? C5 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 89.42(4) 2_655 . ? O1 Cu1 O1 168.5(4) 2_655 4_565 ? O1 Cu1 O1 89.42(4) . 4_565 ? O1 Cu1 O1 89.42(4) 2_655 3_665 ? O1 Cu1 O1 168.5(4) . 3_665 ? O1 Cu1 O1 89.43(4) 4_565 3_665 ? O1 Cu1 O1W 95.75(19) 2_655 . ? O1 Cu1 O1W 95.75(19) . . ? O1 Cu1 O1W 95.75(19) 4_565 . ? O1 Cu1 O1W 95.75(19) 3_665 . ? O1 Cu1 Cu1 84.25(19) 2_655 17_666 ? O1 Cu1 Cu1 84.25(19) . 17_666 ? O1 Cu1 Cu1 84.25(19) 4_565 17_666 ? O1 Cu1 Cu1 84.25(19) 3_665 17_666 ? O1W Cu1 Cu1 180.000(1) . 17_666 ? C1 O1 Cu1 123.6(6) . . ? O1 C1 O1 124.3(11) 19_556 . ? O1 C1 C2 117.8(5) 19_556 . ? O1 C1 C2 117.8(5) . . ? C3 C2 C3 63.3(12) 7_656 19_556 ? C3 C2 C3 120.6(13) 7_656 . ? C3 C2 C3 87.6(12) 19_556 . ? C3 C2 C3 87.6(12) 7_656 21_655 ? C3 C2 C3 120.6(13) 19_556 21_655 ? C3 C2 C3 63.3(12) . 21_655 ? C3 C2 C1 119.7(6) 7_656 . ? C3 C2 C1 119.7(6) 19_556 . ? C3 C2 C1 119.7(6) . . ? C3 C2 C1 119.7(6) 21_655 . ? C3 C3 C2 119.7(6) 23_575 . ? C3 C3 C4 118.9(11) 23_575 . ? C2 C3 C4 121.0(14) . . ? C3 C3 C3 46.6(8) 23_575 3_675 ? C2 C3 C3 87.7(9) . 3_675 ? C4 C3 C3 141.3(11) . 3_675 ? C5 C4 C3 120.6(19) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C5 C5 C4 120.4(11) 23_575 . ? C5 C5 H5 119.8 23_575 . ? C4 C5 H5 119.8 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.811 _refine_diff_density_min -0.509 _refine_diff_density_rms 0.180 #===END # Attachment 'compound3_variable.cif' data_i4mmm _database_code_depnum_ccdc_archive 'CCDC 756942' #TrackingRef 'compound3_variable.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? #'C12 H4 Cu O4, (H2 O)1.63' _chemical_formula_moiety 'C12 H4 Cu O4, O1.63' _chemical_formula_sum 'C12 H4 Cu O5.63' _chemical_formula_weight 301.73 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_Hall '-I 4 2' _symmetry_space_group_name_H-M 'I 4/m m m' _symmetry_Int_Tables_number 139 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x, z' '-x, -y, z' 'y, -x, z' 'x, -y, -z' 'y, x, -z' '-x, y, -z' '-y, -x, -z' 'x+1/2, y+1/2, z+1/2' '-y+1/2, x+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, z+1/2' 'x+1/2, -y+1/2, -z+1/2' 'y+1/2, x+1/2, -z+1/2' '-x+1/2, y+1/2, -z+1/2' '-y+1/2, -x+1/2, -z+1/2' '-x, -y, -z' 'y, -x, -z' 'x, y, -z' '-y, x, -z' '-x, y, z' '-y, -x, z' 'x, -y, z' 'y, x, z' '-x+1/2, -y+1/2, -z+1/2' 'y+1/2, -x+1/2, -z+1/2' 'x+1/2, y+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' '-x+1/2, y+1/2, z+1/2' '-y+1/2, -x+1/2, z+1/2' 'x+1/2, -y+1/2, z+1/2' 'y+1/2, x+1/2, z+1/2' _cell_length_a 10.8058(6) _cell_length_b 10.8058(6) _cell_length_c 14.2168(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1660.0(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 ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 1.326 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _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 7515 _diffrn_reflns_av_R_equivalents 0.0683 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.53 _reflns_number_total 579 _reflns_number_gt 531 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1558P)^2^+11.7658P] 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 SHELXL _refine_ls_extinction_coef 0.016(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 579 _refine_ls_number_parameters 59 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0832 _refine_ls_wR_factor_ref 0.2509 _refine_ls_wR_factor_gt 0.2472 _refine_ls_goodness_of_fit_ref 1.200 _refine_ls_restrained_S_all 1.186 _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 0.5000 0.5000 0.40788(10) 0.0229(8) Uani 1 8 d S . . O1 O 0.5000 0.6782(6) 0.4217(4) 0.0503(19) Uani 1 2 d S . . O1W O 0.5000 0.5000 0.2601(9) 0.059(4) Uani 1 8 d S . . C1 C 0.5000 0.7330(10) 0.5000 0.026(2) Uani 1 4 d S . . C2 C 0.5000 0.8706(9) 0.5000 0.0254(19) Uani 1 4 d S . . C3 C 0.4315(12) 0.9356(11) 0.4318(7) 0.034(2) Uani 0.50 1 d P . . C4 C 0.349(2) 0.871(2) 0.3680(14) 0.037(5) Uani 0.25 1 d P . . H4 H 0.3510 0.7855 0.3652 0.045 Uiso 0.25 1 calc PR . . C5 C 0.268(3) 0.9362(9) 0.3112(17) 0.049(7) Uani 0.25 1 d PD . . H5 H 0.2133 0.8935 0.2728 0.059 Uiso 0.25 1 calc PR . . O2W O 0.137(4) 1.137(4) 0.5000 0.0429(18) Uani 0.16(2) 4 d SPU . . O3W O 0.2500 0.2500 0.2500 0.0449(18) Uani 0.15(2) 4 d SPU . . 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 0.0274(9) 0.0274(9) 0.0140(10) 0.000 0.000 0.000 O1 0.098(6) 0.025(3) 0.027(3) 0.002(2) 0.000 0.000 O1W 0.077(6) 0.077(6) 0.023(6) 0.000 0.000 0.000 C1 0.016(4) 0.033(5) 0.030(5) 0.000 0.000 0.000 C2 0.029(5) 0.026(5) 0.022(4) 0.000 0.000 0.000 C3 0.050(7) 0.033(5) 0.019(4) -0.003(4) -0.010(5) -0.001(5) C4 0.056(14) 0.033(10) 0.022(9) -0.013(8) -0.013(9) 0.003(10) C5 0.083(19) 0.026(11) 0.039(11) 0.004(9) -0.032(13) 0.011(12) O2W 0.0429(18) 0.0429(18) 0.043(2) 0.000 0.000 -0.0001(10) O3W 0.0449(18) 0.0449(18) 0.045(2) 0.0000(7) 0.0000(7) 0.0000(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 Cu1 O1 1.936(6) . ? Cu1 O1 1.936(6) 3_665 ? Cu1 O1 1.936(6) 2_655 ? Cu1 O1 1.936(6) 4_565 ? Cu1 O1W 2.101(13) . ? Cu1 Cu1 2.619(3) 17_666 ? O1 C1 1.261(7) . ? C1 O1 1.261(7) 19_556 ? C1 C2 1.487(14) . ? C2 C3 1.408(12) 7_656 ? C2 C3 1.408(12) 21_655 ? C2 C3 1.408(12) . ? C2 C3 1.408(12) 19_556 ? C3 C3 1.39(2) 23_575 ? C3 C4 1.45(2) . ? C4 C5 1.38(3) . ? C4 H4 0.9300 . ? C5 C5 1.378(19) 23_575 ? C5 H5 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 168.4(3) . 3_665 ? O1 Cu1 O1 89.41(4) . 2_655 ? O1 Cu1 O1 89.41(4) 3_665 2_655 ? O1 Cu1 O1 89.41(4) . 4_565 ? O1 Cu1 O1 89.41(4) 3_665 4_565 ? O1 Cu1 O1 168.4(3) 2_655 4_565 ? O1 Cu1 O1W 95.82(17) . . ? O1 Cu1 O1W 95.82(17) 3_665 . ? O1 Cu1 O1W 95.82(17) 2_655 . ? O1 Cu1 O1W 95.82(17) 4_565 . ? O1 Cu1 Cu1 84.18(17) . 17_666 ? O1 Cu1 Cu1 84.18(17) 3_665 17_666 ? O1 Cu1 Cu1 84.18(17) 2_655 17_666 ? O1 Cu1 Cu1 84.18(17) 4_565 17_666 ? O1W Cu1 Cu1 180.000(1) . 17_666 ? C1 O1 Cu1 123.8(6) . . ? O1 C1 O1 124.0(10) . 19_556 ? O1 C1 C2 118.0(5) . . ? O1 C1 C2 118.0(5) 19_556 . ? C3 C2 C3 87.1(11) 7_656 21_655 ? C3 C2 C3 120.2(11) 7_656 . ? C3 C2 C3 63.5(11) 21_655 . ? C3 C2 C3 63.5(11) 7_656 19_556 ? C3 C2 C3 120.2(11) 21_655 19_556 ? C3 C2 C3 87.1(10) . 19_556 ? C3 C2 C1 119.9(6) 7_656 . ? C3 C2 C1 119.9(6) 21_655 . ? C3 C2 C1 119.9(6) . . ? C3 C2 C1 119.9(6) 19_556 . ? C3 C3 C2 119.9(6) 23_575 . ? C3 C3 C4 118.6(10) 23_575 . ? C2 C3 C4 121.1(13) . . ? C3 C3 C3 46.8(7) 23_575 3_675 ? C2 C3 C3 87.6(8) . 3_675 ? C4 C3 C3 140.9(11) . 3_675 ? C5 C4 C3 120.9(18) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C5 C5 C4 120.4(11) 23_575 . ? C5 C5 H5 119.8 23_575 . ? C4 C5 H5 119.8 . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.760 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.175