# 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_New _database_code_depnum_ccdc_archive 'CCDC 913334' #TrackingRef 'DuanXing.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H18 Cu2 O10' _chemical_formula_weight 653.51 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 Hexagonal _symmetry_space_group_name_H-M P63/mmc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x-y, x, z+1/2' '-y, x-y, z' '-x, -y, z+1/2' '-x+y, -x, z' 'y, -x+y, z+1/2' '-y, -x, -z+1/2' 'x-y, -y, -z' 'x, x-y, -z+1/2' 'y, x, -z' '-x+y, y, -z+1/2' '-x, -x+y, -z' '-x, -y, -z' '-x+y, -x, -z-1/2' 'y, -x+y, -z' 'x, y, -z-1/2' 'x-y, x, -z' '-y, x-y, -z-1/2' 'y, x, z-1/2' '-x+y, y, z' '-x, -x+y, z-1/2' '-y, -x, z' 'x-y, -y, z-1/2' 'x, x-y, z' _cell_length_a 18.2512(8) _cell_length_b 18.2512(8) _cell_length_c 34.2802(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 9889.1(7) _cell_formula_units_Z 6 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 50833 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 25.35 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1980 _exptl_absorpt_coefficient_mu 0.669 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.733 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_process_details CrysAlisPro _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% ? _diffrn_reflns_number 50833 _diffrn_reflns_av_R_equivalents 0.0704 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3379 _reflns_number_gt 2204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd., 2010)' _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. ; # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.052 -0.034 -0.001 6753 873 ' ' _platon_squeeze_details ; ; _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^)+(0.0561P)^2^+5.3370P] 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 3379 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1067 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1836 _refine_ls_wR_factor_gt 0.1712 _refine_ls_goodness_of_fit_ref 1.222 _refine_ls_restrained_S_all 1.222 _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 0.47471(2) -0.05057(4) 0.030968(15) 0.1029(4) Uani 1 2 d S . . O1 O 0.5865(2) 0.02383(18) 0.05131(7) 0.1176(12) Uani 1 1 d . . . O2 O 0.6292(2) 0.10954(17) -0.00140(7) 0.1200(12) Uani 1 1 d . . . O3 O 0.43489(19) -0.1302(4) 0.08083(16) 0.192(3) Uani 1 2 d S . . C1 C 0.6391(3) 0.0876(3) 0.03282(11) 0.1029(15) Uani 1 1 d . . . C2 C 0.7803(2) 0.2197(2) 0.03365(15) 0.0997(19) Uani 1 2 d S . . H2A H 0.7696 0.2304 0.0084 0.120 Uiso 1 2 calc SR . . C3 C 0.7213(3) 0.1459(3) 0.05131(10) 0.1051(16) Uani 1 1 d . . . C4 C 0.7414(4) 0.1309(3) 0.08868(11) 0.1189(18) Uani 1 1 d . . . H4A H 0.7044 0.0803 0.1011 0.143 Uiso 1 1 calc R . . C5 C 0.8126(2) 0.1874(2) 0.10750(16) 0.108(2) Uani 1 2 d S A . C6 C 0.8271(3) 0.1729(3) 0.15108(16) 0.125(3) Uani 1 2 d S . . C7 C 0.8056(10) 0.0956(8) 0.1637(3) 0.148(4) Uani 0.50 1 d P A 1 H7A H 0.7835 0.0468 0.1459 0.177 Uiso 0.50 1 d P B 1 C8 C 0.8145(8) 0.0837(8) 0.2028(3) 0.145(4) Uani 0.50 1 d P A 1 H8A H 0.7999 0.0303 0.2122 0.174 Uiso 0.50 1 calc PR A 1 C7' C 0.8533(7) 0.2413(7) 0.1766(2) 0.123(4) Uani 0.50 1 d P A 2 H7'A H 0.8653 0.2986 0.1675 0.147 Uiso 0.50 1 d P C 2 C8' C 0.8582(7) 0.2225(7) 0.2163(2) 0.124(4) Uani 0.50 1 d P A 2 C9 C 0.8462(4) 0.1538(4) 0.22868(19) 0.127(3) Uani 1 2 d S . . C10 C 0.8776(11) 0.2864(11) 0.2500 0.156(7) Uani 0.50 2 d SP . . H10A H 0.8400 0.3096 0.2500 0.187 Uiso 0.50 2 calc SPR A 2 H10B H 0.9361 0.3318 0.2500 0.187 Uiso 0.50 2 calc SPR A 2 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 0.1767(8) 0.0589(4) 0.0339(3) -0.0041(3) -0.00206(14) 0.0294(2) O1 0.172(3) 0.0785(19) 0.0537(15) 0.0007(14) -0.0043(18) 0.026(2) O2 0.175(3) 0.0827(19) 0.0497(14) -0.0063(13) -0.0106(18) 0.0247(19) O3 0.265(6) 0.146(5) 0.125(4) 0.084(4) 0.0421(19) 0.073(2) C1 0.135(4) 0.082(3) 0.048(2) -0.022(2) -0.011(2) 0.022(3) C2 0.126(4) 0.126(4) 0.044(3) -0.0080(16) 0.0080(16) 0.060(5) C3 0.153(4) 0.100(3) 0.043(2) -0.001(2) 0.011(2) 0.049(3) C4 0.166(5) 0.108(4) 0.052(2) -0.013(2) -0.004(3) 0.045(4) C5 0.128(4) 0.128(4) 0.049(3) -0.0032(17) 0.0032(17) 0.049(5) C6 0.152(5) 0.152(5) 0.041(3) -0.003(2) 0.003(2) 0.055(6) C7 0.228(13) 0.147(10) 0.067(6) 0.007(6) -0.011(7) 0.093(10) C8 0.220(12) 0.176(11) 0.060(5) 0.001(6) 0.002(7) 0.115(10) C7' 0.139(8) 0.148(8) 0.043(4) -0.029(5) -0.013(5) 0.043(7) C8' 0.150(9) 0.125(9) 0.041(5) 0.001(5) 0.006(5) 0.027(7) C9 0.161(6) 0.161(6) 0.049(4) -0.004(2) 0.004(2) 0.072(7) C10 0.169(14) 0.188(16) 0.025(5) 0.000 0.000 0.025(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.930(3) . ? Cu1 O1 1.930(3) 20_655 ? Cu1 O2 1.934(3) 8 ? Cu1 O2 1.934(3) 13_655 ? Cu1 O3 2.123(4) . ? Cu1 Cu1 2.6578(12) 13_655 ? O1 C1 1.250(5) . ? O2 C1 1.281(5) . ? O2 Cu1 1.934(3) 13_655 ? C1 C3 1.479(6) . ? C2 C3 1.375(5) 22_665 ? C2 C3 1.375(5) . ? C2 H2A 0.9300 . ? C3 C4 1.397(6) . ? C4 C5 1.353(5) . ? C4 H4A 0.9300 . ? C5 C4 1.353(5) 22_665 ? C5 C6 1.562(8) . ? C6 C7 1.335(12) 22_665 ? C6 C7 1.335(12) . ? C6 C7' 1.398(11) . ? C6 C7' 1.398(11) 22_665 ? C7 C8 1.381(12) . ? C7 C7 1.80(3) 22_665 ? C7 H7A 0.9834 . ? C8 C9 1.420(12) . ? C8 C8 1.86(3) 22_665 ? C8 H8A 0.9300 . ? C7' C8' 1.417(11) . ? C7' C7' 1.73(2) 22_665 ? C7' H7'A 1.0049 . ? C8' C9 1.233(12) . ? C8' C8' 1.47(2) 22_665 ? C8' C10 1.552(16) . ? C9 C8' 1.233(12) 22_665 ? C9 C8 1.420(12) 22_665 ? C9 C9 1.462(13) 16_556 ? C10 C8' 1.552(16) 16_556 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? 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 89.8(2) . 20_655 ? O1 Cu1 O2 89.27(14) . 8 ? O1 Cu1 O2 168.14(11) 20_655 8 ? O1 Cu1 O2 168.14(11) . 13_655 ? O1 Cu1 O2 89.27(14) 20_655 13_655 ? O2 Cu1 O2 89.2(2) 8 13_655 ? O1 Cu1 O3 94.04(16) . . ? O1 Cu1 O3 94.04(16) 20_655 . ? O2 Cu1 O3 97.83(15) 8 . ? O2 Cu1 O3 97.83(15) 13_655 . ? O1 Cu1 Cu1 85.53(8) . 13_655 ? O1 Cu1 Cu1 85.53(8) 20_655 13_655 ? O2 Cu1 Cu1 82.60(8) 8 13_655 ? O2 Cu1 Cu1 82.60(8) 13_655 13_655 ? O3 Cu1 Cu1 179.4(2) . 13_655 ? C1 O1 Cu1 121.4(3) . . ? C1 O2 Cu1 123.9(3) . 13_655 ? O1 C1 O2 126.4(4) . . ? O1 C1 C3 118.9(4) . . ? O2 C1 C3 114.8(4) . . ? C3 C2 C3 123.6(6) 22_665 . ? C3 C2 H2A 118.2 22_665 . ? C3 C2 H2A 118.2 . . ? C2 C3 C4 116.3(5) . . ? C2 C3 C1 122.1(4) . . ? C4 C3 C1 121.5(4) . . ? C5 C4 C3 122.3(5) . . ? C5 C4 H4A 118.9 . . ? C3 C4 H4A 118.9 . . ? C4 C5 C4 119.1(6) . 22_665 ? C4 C5 C6 120.4(3) . . ? C4 C5 C6 120.4(3) 22_665 . ? C7 C6 C7 84.9(15) 22_665 . ? C7 C6 C7' 72.3(7) 22_665 . ? C7 C6 C7' 122.0(7) . . ? C7 C6 C7' 122.0(7) 22_665 22_665 ? C7 C6 C7' 72.3(7) . 22_665 ? C7' C6 C7' 76.3(9) . 22_665 ? C7 C6 C5 120.2(6) 22_665 . ? C7 C6 C5 120.2(6) . . ? C7' C6 C5 117.3(7) . . ? C7' C6 C5 117.3(7) 22_665 . ? C6 C7 C8 119.0(11) . . ? C6 C7 C7 47.5(7) . 22_665 ? C8 C7 C7 91.1(8) . 22_665 ? C6 C7 H7A 121.8 . . ? C8 C7 H7A 119.2 . . ? C7 C7 H7A 131.1 22_665 . ? C7 C8 C9 119.4(11) . . ? C7 C8 C8 88.9(8) . 22_665 ? C9 C8 C8 49.2(5) . 22_665 ? C7 C8 H8A 120.3 . . ? C9 C8 H8A 120.3 . . ? C8 C8 H8A 131.9 22_665 . ? C6 C7' C8' 114.8(10) . . ? C6 C7' C7' 51.9(5) . 22_665 ? C8' C7' C7' 84.8(6) . 22_665 ? C6 C7' H7'A 122.2 . . ? C8' C7' H7'A 123.0 . . ? C7' C7' H7'A 129.0 22_665 . ? C9 C8' C7' 125.2(10) . . ? C9 C8' C8' 53.4(7) . 22_665 ? C7' C8' C8' 95.2(6) . 22_665 ? C9 C8' C10 111.4(9) . . ? C7' C8' C10 123.4(11) . . ? C8' C8' C10 119.3(7) 22_665 . ? C8' C9 C8' 73.3(13) . 22_665 ? C8' C9 C8 72.9(7) . 22_665 ? C8' C9 C8 119.0(9) 22_665 22_665 ? C8' C9 C8 119.0(9) . . ? C8' C9 C8 72.9(7) 22_665 . ? C8 C9 C8 81.7(11) 22_665 . ? C8' C9 C9 110.2(6) . 16_556 ? C8' C9 C9 110.2(6) 22_665 16_556 ? C8 C9 C9 128.6(5) 22_665 16_556 ? C8 C9 C9 128.6(5) . 16_556 ? C8' C10 C8' 96.3(13) . 16_556 ? C8' C10 H10A 112.5 . . ? C8' C10 H10A 112.5 16_556 . ? C8' C10 H10B 112.5 . . ? C8' C10 H10B 112.5 16_556 . ? H10A C10 H10B 110.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.585 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.054