data_zhu40 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H12 Cu2 O6' _chemical_formula_sum 'C6 H12 Cu2 O6' _chemical_formula_weight 307.24 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 Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall -C2yc 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 11.3067(18) _cell_length_b 9.8359(18) _cell_length_c 17.993(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.869(3) _cell_angle_gamma 90.00 _cell_volume 1996.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1794 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 27.31 _exptl_crystal_description flat _exptl_crystal_colour black _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.044 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 4.260 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7004 _exptl_absorpt_correction_T_max 0.7841 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6429 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2029 _reflns_number_gt 1301 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2029 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_gt 0.1245 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.010 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.87200(6) 0.20199(7) 0.72333(4) 0.0199(3) Uani 1 1 d . . . Cu2 Cu 0.87138(6) -0.09867(7) 0.72562(5) 0.0204(3) Uani 1 1 d . . . C1 C 0.6822(5) 0.0528(6) 0.7913(3) 0.0176(13) Uani 1 1 d . . . C2 C 0.5736(6) 0.0548(6) 0.8336(4) 0.0281(15) Uani 1 1 d . . . H2A H 0.5963 0.0574 0.8871 0.042 Uiso 1 1 calc R . . H2B H 0.5267 -0.0272 0.8220 0.042 Uiso 1 1 calc R . . H2C H 0.5263 0.1354 0.8196 0.042 Uiso 1 1 calc R . . C3 C 0.7696(6) 0.0524(7) 0.5979(4) 0.0264(15) Uani 1 1 d . . . C4 C 0.7049(7) 0.0480(7) 0.5222(4) 0.0365(18) Uani 1 1 d . . . H4A H 0.6192 0.0496 0.5276 0.055 Uiso 1 1 calc R . . H4B H 0.7259 -0.0355 0.4965 0.055 Uiso 1 1 calc R . . H4C H 0.7273 0.1271 0.4931 0.055 Uiso 1 1 calc R . . C5 C 1.0582(6) 0.2324(7) 0.6121(4) 0.0305(16) Uani 1 1 d . . . H5A H 1.0320 0.3195 0.5904 0.046 Uiso 1 1 calc R . . H5B H 1.0194 0.1578 0.5837 0.046 Uiso 1 1 calc R . . H5C H 1.1444 0.2242 0.6104 0.046 Uiso 1 1 calc R . . C6 C 1.0528(6) -0.1298(7) 0.6109(4) 0.0308(16) Uani 1 1 d . . . H6A H 1.0440 -0.0391 0.5886 0.046 Uiso 1 1 calc R . . H6B H 0.9991 -0.1934 0.5835 0.046 Uiso 1 1 calc R . . H6C H 1.1348 -0.1608 0.6082 0.046 Uiso 1 1 calc R . . O1 O 0.7254(3) 0.1658(4) 0.7735(2) 0.0248(10) Uani 1 1 d . . . O2 O 0.7284(4) -0.0617(4) 0.7784(3) 0.0246(10) Uani 1 1 d . . . O3 O 0.7957(4) 0.1663(4) 0.6256(2) 0.0268(10) Uani 1 1 d . . . O4 O 0.7911(4) -0.0617(4) 0.6288(3) 0.0290(11) Uani 1 1 d . . . O5 O 1.0278(3) 0.2259(4) 0.6869(2) 0.0233(10) Uani 1 1 d . . . O6 O 1.0242(4) -0.1243(4) 0.6873(2) 0.0225(10) 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 Cu1 0.0116(4) 0.0191(4) 0.0287(5) -0.0003(3) -0.0010(3) -0.0019(3) Cu2 0.0115(4) 0.0197(4) 0.0298(5) 0.0007(3) -0.0001(3) 0.0015(3) C1 0.013(3) 0.017(3) 0.023(3) -0.003(3) 0.000(2) -0.003(3) C2 0.028(4) 0.024(3) 0.033(4) 0.000(3) 0.003(3) 0.004(3) C3 0.017(3) 0.034(4) 0.028(4) 0.001(3) -0.001(3) 0.002(3) C4 0.039(5) 0.040(4) 0.029(4) -0.001(3) -0.008(3) -0.006(3) C5 0.031(4) 0.031(4) 0.030(4) -0.003(3) 0.007(3) -0.007(3) C6 0.022(4) 0.041(4) 0.029(4) 0.001(3) 0.005(3) 0.006(3) O1 0.012(2) 0.022(2) 0.040(3) 0.003(2) 0.001(2) -0.0027(19) O2 0.015(2) 0.018(2) 0.040(3) 0.005(2) 0.004(2) 0.0038(19) O3 0.021(2) 0.027(2) 0.031(3) 0.001(2) -0.005(2) -0.005(2) O4 0.022(3) 0.027(2) 0.037(3) -0.002(2) -0.004(2) 0.001(2) O5 0.011(2) 0.034(3) 0.025(3) 0.000(2) -0.0001(18) -0.0008(19) O6 0.016(2) 0.026(2) 0.026(3) -0.0021(19) 0.0027(19) -0.0036(19) _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 O5 1.924(4) 2_756 ? Cu1 O5 1.935(4) . ? Cu1 O3 1.938(4) . ? Cu1 O1 1.973(4) . ? Cu1 Cu2 2.9576(11) . ? Cu1 Cu1 2.9873(15) 2_756 ? Cu2 O6 1.914(4) 2_756 ? Cu2 O6 1.919(4) . ? Cu2 O4 1.943(5) . ? Cu2 O2 1.963(5) . ? Cu2 Cu2 2.9808(15) 2_756 ? C1 O1 1.264(7) . ? C1 O2 1.270(7) . ? C1 C2 1.487(9) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 O3 1.253(7) . ? C3 O4 1.269(7) . ? C3 C4 1.502(9) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 O5 1.412(7) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 O6 1.435(7) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O5 Cu1 1.924(4) 2_756 ? O6 Cu2 1.914(4) 2_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 O5 Cu1 O5 76.8(2) 2_756 . ? O5 Cu1 O3 170.06(18) 2_756 . ? O5 Cu1 O3 94.23(18) . . ? O5 Cu1 O1 95.91(18) 2_756 . ? O5 Cu1 O1 171.62(17) . . ? O3 Cu1 O1 92.67(18) . . ? O5 Cu1 Cu2 96.44(13) 2_756 . ? O5 Cu1 Cu2 97.42(13) . . ? O3 Cu1 Cu2 80.23(13) . . ? O1 Cu1 Cu2 79.07(12) . . ? O5 Cu1 Cu1 39.42(12) 2_756 2_756 ? O5 Cu1 Cu1 39.15(12) . 2_756 ? O3 Cu1 Cu1 130.83(14) . 2_756 ? O1 Cu1 Cu1 132.75(13) . 2_756 ? Cu2 Cu1 Cu1 89.93(2) . 2_756 ? O6 Cu2 O6 75.9(2) 2_756 . ? O6 Cu2 O4 169.55(19) 2_756 . ? O6 Cu2 O4 94.58(19) . . ? O6 Cu2 O2 96.40(18) 2_756 . ? O6 Cu2 O2 171.32(18) . . ? O4 Cu2 O2 92.78(19) . . ? O6 Cu2 Cu1 98.11(13) 2_756 . ? O6 Cu2 Cu1 97.07(13) . . ? O4 Cu2 Cu1 78.56(13) . . ? O2 Cu2 Cu1 79.89(12) . . ? O6 Cu2 Cu2 39.02(13) 2_756 2_756 ? O6 Cu2 Cu2 38.89(12) . 2_756 ? O4 Cu2 Cu2 130.64(15) . 2_756 ? O2 Cu2 Cu2 132.59(14) . 2_756 ? Cu1 Cu2 Cu2 90.05(2) . 2_756 ? O1 C1 O2 124.2(6) . . ? O1 C1 C2 117.7(5) . . ? O2 C1 C2 118.0(5) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O3 C3 O4 125.7(6) . . ? O3 C3 C4 118.3(6) . . ? O4 C3 C4 116.1(6) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O5 C5 H5A 109.5 . . ? O5 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O5 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? O6 C6 H6A 109.5 . . ? O6 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O6 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 O1 Cu1 128.7(4) . . ? C1 O2 Cu2 128.0(4) . . ? C3 O3 Cu1 127.0(4) . . ? C3 O4 Cu2 128.5(4) . . ? C5 O5 Cu1 129.6(4) . 2_756 ? C5 O5 Cu1 127.9(4) . . ? Cu1 O5 Cu1 101.43(19) 2_756 . ? C6 O6 Cu2 128.5(4) . 2_756 ? C6 O6 Cu2 128.0(4) . . ? Cu2 O6 Cu2 102.1(2) 2_756 . ? 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 O5 Cu1 Cu2 O6 -2.26(17) 2_756 . . 2_756 ? O5 Cu1 Cu2 O6 75.23(18) . . . 2_756 ? O3 Cu1 Cu2 O6 168.27(19) . . . 2_756 ? O1 Cu1 Cu2 O6 -97.06(18) . . . 2_756 ? Cu1 Cu1 Cu2 O6 36.69(13) 2_756 . . 2_756 ? O5 Cu1 Cu2 O6 -78.94(18) 2_756 . . . ? O5 Cu1 Cu2 O6 -1.44(16) . . . . ? O3 Cu1 Cu2 O6 91.60(18) . . . . ? O1 Cu1 Cu2 O6 -173.74(17) . . . . ? Cu1 Cu1 Cu2 O6 -39.98(13) 2_756 . . . ? O5 Cu1 Cu2 O4 -172.21(19) 2_756 . . . ? O5 Cu1 Cu2 O4 -94.72(19) . . . . ? O3 Cu1 Cu2 O4 -1.67(18) . . . . ? O1 Cu1 Cu2 O4 92.99(19) . . . . ? Cu1 Cu1 Cu2 O4 -133.25(15) 2_756 . . . ? O5 Cu1 Cu2 O2 92.84(18) 2_756 . . . ? O5 Cu1 Cu2 O2 170.33(18) . . . . ? O3 Cu1 Cu2 O2 -96.63(19) . . . . ? O1 Cu1 Cu2 O2 -1.96(17) . . . . ? Cu1 Cu1 Cu2 O2 131.79(14) 2_756 . . . ? O5 Cu1 Cu2 Cu2 -40.58(13) 2_756 . . 2_756 ? O5 Cu1 Cu2 Cu2 36.91(13) . . . 2_756 ? O3 Cu1 Cu2 Cu2 129.96(14) . . . 2_756 ? O1 Cu1 Cu2 Cu2 -135.38(13) . . . 2_756 ? Cu1 Cu1 Cu2 Cu2 -1.62(4) 2_756 . . 2_756 ? O2 C1 O1 Cu1 -0.7(9) . . . . ? C2 C1 O1 Cu1 176.0(4) . . . . ? O5 Cu1 O1 C1 -93.4(5) 2_756 . . . ? O3 Cu1 O1 C1 81.6(5) . . . . ? Cu2 Cu1 O1 C1 2.1(5) . . . . ? Cu1 Cu1 O1 C1 -77.6(5) 2_756 . . . ? O1 C1 O2 Cu2 -2.6(9) . . . . ? C2 C1 O2 Cu2 -179.2(4) . . . . ? O6 Cu2 O2 C1 100.1(5) 2_756 . . . ? O4 Cu2 O2 C1 -74.9(5) . . . . ? Cu1 Cu2 O2 C1 2.9(5) . . . . ? Cu2 Cu2 O2 C1 83.6(5) 2_756 . . . ? O4 C3 O3 Cu1 -1.6(10) . . . . ? C4 C3 O3 Cu1 177.0(5) . . . . ? O5 Cu1 O3 C3 99.0(5) . . . . ? O1 Cu1 O3 C3 -76.2(5) . . . . ? Cu2 Cu1 O3 C3 2.2(5) . . . . ? Cu1 Cu1 O3 C3 83.5(5) 2_756 . . . ? O3 C3 O4 Cu2 -1.1(10) . . . . ? C4 C3 O4 Cu2 -179.7(4) . . . . ? O6 Cu2 O4 C3 -70.3(12) 2_756 . . . ? O6 Cu2 O4 C3 -94.3(6) . . . . ? O2 Cu2 O4 C3 81.1(6) . . . . ? Cu1 Cu2 O4 C3 2.0(5) . . . . ? Cu2 Cu2 O4 C3 -78.1(6) 2_756 . . . ? O5 Cu1 O5 C5 -176.5(4) 2_756 . . . ? O3 Cu1 O5 C5 7.9(5) . . . . ? Cu2 Cu1 O5 C5 88.5(5) . . . . ? Cu1 Cu1 O5 C5 169.2(6) 2_756 . . . ? O5 Cu1 O5 Cu1 14.2(3) 2_756 . . 2_756 ? O3 Cu1 O5 Cu1 -161.3(2) . . . 2_756 ? Cu2 Cu1 O5 Cu1 -80.67(16) . . . 2_756 ? O6 Cu2 O6 C6 177.2(4) 2_756 . . . ? O4 Cu2 O6 C6 -7.2(5) . . . . ? Cu1 Cu2 O6 C6 -86.2(5) . . . . ? Cu2 Cu2 O6 C6 -167.4(6) 2_756 . . . ? O6 Cu2 O6 Cu2 -15.4(3) 2_756 . . 2_756 ? O4 Cu2 O6 Cu2 160.25(19) . . . 2_756 ? Cu1 Cu2 O6 Cu2 81.24(16) . . . 2_756 ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.170 _refine_diff_density_min -1.014 _refine_diff_density_rms 0.241