# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Shengqian Ma' _publ_contact_author_email SMA@ANL.GOV _publ_section_title ; An Unusual Case of Symmetry-Preserving Isomerism ; loop_ _publ_author_name 'Shengqian Ma' 'Jian-Rong Li' 'Jason M Simmons' 'Daofeng Sun' 'Daqiang Yuan' 'Hong-Cai Zhou' data_pcn16 _database_code_depnum_ccdc_archive 'CCDC 709273' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common PCN-16 _chemical_melting_point 'NOT MEASURED' _chemical_formula_moiety 'Cu9 (C18H6O8)4.5 (H2O)9' _chemical_formula_sum 'C81 H45 Cu9 O45' _chemical_formula_weight 2310.03 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 trigonal _symmetry_space_group_name_H-M R-3m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z' '-x, -x+y, -z' 'y, x, -z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+1/3' '-x+2/3, -x+y+1/3, -z+1/3' 'y+2/3, x+1/3, -z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+2/3' '-x+1/3, -x+y+2/3, -z+2/3' 'y+1/3, x+2/3, -z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z' 'x, x-y, z' '-y, -x, z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-y+2/3, -x+1/3, z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' '-y+1/3, -x+2/3, z+2/3' _cell_length_a 18.837(8) _cell_length_b 18.837(8) _cell_length_c 32.120(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 9870(8) _cell_formula_units_Z 2 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 2781 _cell_measurement_theta_min 2.801 _cell_measurement_theta_max 26.385 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 0.777 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 0.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8985 _exptl_absorpt_correction_T_max 0.9247 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 2433 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0564 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 26.41 _reflns_number_total 2433 _reflns_number_gt 1646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0575P)^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 2433 _refine_ls_number_parameters 76 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0551 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1012 _refine_ls_wR_factor_gt 0.0987 _refine_ls_goodness_of_fit_ref 0.859 _refine_ls_restrained_S_all 0.859 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 # 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 -0.031 -0.020 -0.002 6771 1891 ' ' _platon_squeeze_details ; ; 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 -0.04498(2) 0.477511(12) 0.465271(12) 0.04183(17) Uani 1 2 d S . . O1 O 0.03412(11) 0.59006(12) 0.44910(6) 0.0644(6) Uani 1 1 d . . . O2 O 0.11082(11) 0.62753(11) 0.50701(6) 0.0621(5) Uani 1 1 d . . . O3 O -0.1048(3) 0.44760(13) 0.40630(10) 0.1195(14) Uani 1 2 d S . . C1 C 0.1738(2) 0.8262(2) 0.35011(16) 0.0924(17) Uani 1 2 d S . . C2 C 0.22499(13) 0.77501(13) 0.47028(12) 0.0584(10) Uani 1 2 d S . . H2 H 0.2364 0.7636 0.4971 0.070 Uiso 1 2 calc SR . . C3 C 0.15297(17) 0.71960(17) 0.45075(9) 0.0596(7) Uani 1 1 d . . . C4 C 0.19051(16) 0.80949(16) 0.39104(15) 0.0795(14) Uani 1 2 d S . . C5 C 0.13502(19) 0.73630(19) 0.41130(9) 0.0747(10) Uani 1 1 d . . . H5 H 0.0858 0.6987 0.3981 0.090 Uiso 1 1 calc R . . C7 C 0.09436(16) 0.64038(17) 0.47101(9) 0.0551(7) 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 0.0277(2) 0.0498(2) 0.0407(2) -0.00213(9) -0.00427(18) 0.01384(12) O1 0.0465(11) 0.0572(12) 0.0621(11) 0.0067(10) -0.0087(9) 0.0054(10) O2 0.0500(12) 0.0538(12) 0.0604(11) 0.0086(9) -0.0054(9) 0.0094(9) O3 0.124(3) 0.144(3) 0.084(2) -0.0316(11) -0.063(2) 0.0622(16) C1 0.078(2) 0.078(2) 0.082(3) 0.0207(17) -0.0207(17) 0.009(3) C2 0.0531(17) 0.0531(17) 0.063(2) 0.0029(10) -0.0029(10) 0.022(2) C3 0.0495(17) 0.0476(16) 0.0645(17) 0.0067(14) -0.0058(14) 0.0115(14) C4 0.068(2) 0.068(2) 0.071(3) 0.0162(14) -0.0162(14) 0.010(2) C5 0.0521(18) 0.0572(19) 0.078(2) 0.0120(16) -0.0164(16) -0.0005(15) C7 0.0399(15) 0.0515(16) 0.0649(17) 0.0008(14) 0.0057(13) 0.0161(14) _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 1.9473(19) 5_556 ? Cu1 O1 1.956(2) . ? Cu1 O3 2.131(3) . ? O1 C7 1.267(3) . ? O2 C7 1.252(3) . ? C1 C1 1.175(9) 31_565 ? C1 C4 1.423(6) . ? C2 C3 1.381(3) 24_665 ? C2 C3 1.381(3) . ? C2 H2 0.9400 . ? C3 C5 1.387(4) . ? C3 C7 1.491(4) . ? C4 C5 1.406(4) . ? C4 C5 1.406(4) 24_665 ? C5 H5 0.9400 . ? 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 88.48(12) 19_566 5_556 ? O2 Cu1 O1 89.70(9) 19_566 23_565 ? O2 Cu1 O1 167.36(8) 5_556 23_565 ? O2 Cu1 O1 167.36(8) 19_566 . ? O2 Cu1 O1 89.70(9) 5_556 . ? O1 Cu1 O1 89.34(13) 23_565 . ? O2 Cu1 O3 98.85(10) 19_566 . ? O2 Cu1 O3 98.85(10) 5_556 . ? O1 Cu1 O3 93.78(10) 23_565 . ? O1 Cu1 O3 93.79(10) . . ? O2 Cu1 Cu1 85.47(6) 19_566 19_566 ? O2 Cu1 Cu1 85.47(6) 5_556 19_566 ? O1 Cu1 Cu1 81.92(6) 23_565 19_566 ? O1 Cu1 Cu1 81.91(6) . 19_566 ? O3 Cu1 Cu1 173.92(12) . 19_566 ? C7 O1 Cu1 125.11(18) . . ? C7 O2 Cu1 121.70(18) . 19_566 ? C1 C1 C4 179.0(10) 31_565 . ? C3 C2 C3 120.7(4) 24_665 . ? C3 C2 H2 119.6 24_665 . ? C3 C2 H2 119.7 . . ? C2 C3 C5 120.1(3) . . ? C2 C3 C7 121.0(3) . . ? C5 C3 C7 118.9(3) . . ? C5 C4 C5 119.1(4) . 24_665 ? C5 C4 C1 120.4(2) . . ? C5 C4 C1 120.4(2) 24_665 . ? C3 C5 C4 119.9(3) . . ? C3 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? O2 C7 O1 125.7(3) . . ? O2 C7 C3 117.8(2) . . ? O1 C7 C3 116.4(3) . . ? 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 O2 Cu1 O1 C7 6.0(5) 19_566 . . . ? O2 Cu1 O1 C7 87.7(2) 5_556 . . . ? O1 Cu1 O1 C7 -79.7(2) 23_565 . . . ? O3 Cu1 O1 C7 -173.4(2) . . . . ? Cu1 Cu1 O1 C7 2.2(2) 19_566 . . . ? C3 C2 C3 C5 -0.8(6) 24_665 . . . ? C3 C2 C3 C7 177.7(2) 24_665 . . . ? C2 C3 C5 C4 0.4(6) . . . . ? C7 C3 C5 C4 -178.1(4) . . . . ? C5 C4 C5 C3 -0.1(7) 24_665 . . . ? C1 C4 C5 C3 178.2(5) . . . . ? Cu1 O2 C7 O1 2.0(4) 19_566 . . . ? Cu1 O2 C7 C3 -173.99(19) 19_566 . . . ? Cu1 O1 C7 O2 -3.3(4) . . . . ? Cu1 O1 C7 C3 172.78(19) . . . . ? C2 C3 C7 O2 3.2(4) . . . . ? C5 C3 C7 O2 -178.3(3) . . . . ? C2 C3 C7 O1 -173.2(3) . . . . ? C5 C3 C7 O1 5.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.446 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.062 # start Validation Reply Form _vrf_PLAT432_pcn16 ; PROBLEM: Short Inter X...Y Contact C1 .. C1 .. 1.17 Ang. RESPONSE: In the molecule, the distance is reasonable. ; data_pcn16' _database_code_depnum_ccdc_archive 'CCDC 709274' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common pcn16' _chemical_melting_point 'NOT MEASURED' _chemical_formula_moiety 'Cu9 (C18H6O8)4.5 (H2O)9' _chemical_formula_sum 'C81 H45 Cu9 O45' _chemical_formula_weight 2310.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x-y, -y, -z' '-x, -x+y, -z' 'y, x, -z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x-y+2/3, -y+1/3, -z+1/3' '-x+2/3, -x+y+1/3, -z+1/3' 'y+2/3, x+1/3, -z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'x-y+1/3, -y+2/3, -z+2/3' '-x+1/3, -x+y+2/3, -z+2/3' 'y+1/3, x+2/3, -z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+y, y, z' 'x, x-y, z' '-y, -x, z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+y+2/3, y+1/3, z+1/3' 'x+2/3, x-y+1/3, z+1/3' '-y+2/3, -x+1/3, z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-x+y+1/3, y+2/3, z+2/3' 'x+1/3, x-y+2/3, z+2/3' '-y+1/3, -x+2/3, z+2/3' _cell_length_a 23.773(3) _cell_length_b 23.773(3) _cell_length_c 19.072(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 9335(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas NONE _exptl_crystal_density_diffrn 0.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 1.505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8401 _exptl_absorpt_correction_T_max 0.9020 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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_reflns_number 2034 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 67.99 _reflns_number_total 2034 _reflns_number_gt 1693 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _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^ > 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^)+(0.2000P)^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 SHELXL _refine_ls_extinction_coef 0.00050(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2034 _refine_ls_number_parameters 75 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1242 _refine_ls_R_factor_gt 0.1103 _refine_ls_wR_factor_ref 0.3323 _refine_ls_wR_factor_gt 0.2889 _refine_ls_goodness_of_fit_ref 1.537 _refine_ls_restrained_S_all 1.537 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 # 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 -0.009 -0.006 -0.024 6202 2266 ' ' _platon_squeeze_details ; ; 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 0.26999(4) 0.13499(2) 0.15502(5) 0.0362(6) Uani 1 2 d S . . O1 O 0.27067(19) 0.1941(2) 0.2268(2) 0.0536(11) Uani 1 1 d . . . C1 C 0.3215(3) 0.2380(3) 0.2535(3) 0.0491(15) Uani 1 1 d . . . O2 O 0.37750(19) 0.2468(2) 0.2467(2) 0.0519(10) Uani 1 1 d . . . C2 C 0.3145(3) 0.2859(3) 0.2966(4) 0.0551(16) Uani 1 1 d . . . O3 O 0.1678(3) 0.08390(14) 0.1439(4) 0.0712(19) Uani 1 2 d S . . C3 C 0.3669(3) 0.3333 0.3333 0.050(2) Uani 1 2 d S . . H3 H 0.4069 0.3333 0.3333 0.060 Uiso 1 2 calc SR . . C4 C 0.2566(3) 0.2858(3) 0.2966(4) 0.0654(19) Uani 1 1 d . . . H4 H 0.2204 0.2532 0.2715 0.078 Uiso 1 1 calc R . . C5 C 0.2510(4) 0.3333 0.3333 0.073(3) Uani 1 2 d S . . C6 C 0.1914(4) 0.3333 0.3333 0.082(4) Uani 1 2 d S . . 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 0.0359(7) 0.0288(6) 0.0462(8) -0.00602(19) -0.0120(4) 0.0179(4) O1 0.042(2) 0.050(2) 0.070(3) -0.0254(19) -0.0144(18) 0.0249(18) C1 0.045(3) 0.044(3) 0.063(4) -0.015(3) -0.015(2) 0.025(2) O2 0.041(2) 0.049(2) 0.067(2) -0.0216(19) -0.0098(17) 0.0230(16) C2 0.046(3) 0.057(3) 0.067(4) -0.028(3) -0.014(3) 0.029(3) O3 0.031(3) 0.071(3) 0.098(5) -0.0086(15) -0.017(3) 0.0157(13) C3 0.042(3) 0.047(4) 0.064(5) -0.024(4) -0.012(2) 0.023(2) C4 0.044(3) 0.068(4) 0.088(5) -0.045(4) -0.027(3) 0.031(3) C5 0.049(3) 0.084(7) 0.097(8) -0.055(6) -0.028(3) 0.042(3) C6 0.053(3) 0.077(7) 0.123(9) -0.066(7) -0.033(3) 0.039(3) _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 1.940(4) 25 ? Cu1 O1 1.956(4) . ? Cu1 O3 2.115(6) . ? O1 C1 1.243(7) . ? C1 O2 1.247(7) . ? C1 C2 1.480(8) . ? C2 C4 1.375(9) . ? C2 C3 1.381(7) . ? C3 C2 1.381(7) 16 ? C3 H3 0.9500 . ? C4 C5 1.391(8) . ? C4 H4 0.9500 . ? C5 C4 1.391(8) 16 ? C5 C6 1.419(14) . ? C6 C6 1.17(2) 31 ? 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 90.7(3) 25 11 ? O2 Cu1 O1 87.8(2) 25 23 ? O2 Cu1 O1 167.81(17) 11 23 ? O2 Cu1 O1 167.80(17) 25 . ? O2 Cu1 O1 87.8(2) 11 . ? O1 Cu1 O1 91.2(3) 23 . ? O2 Cu1 O3 97.75(19) 25 . ? O2 Cu1 O3 97.75(19) 11 . ? O1 Cu1 O3 94.44(19) 23 . ? O1 Cu1 O3 94.44(19) . . ? O2 Cu1 Cu1 84.98(12) 25 25 ? O2 Cu1 Cu1 84.97(12) 11 25 ? O1 Cu1 Cu1 82.84(12) 23 25 ? O1 Cu1 Cu1 82.84(12) . 25 ? O3 Cu1 Cu1 176.1(2) . 25 ? C1 O1 Cu1 123.0(4) . . ? O1 C1 O2 127.4(5) . . ? O1 C1 C2 116.0(5) . . ? O2 C1 C2 116.7(5) . . ? C1 O2 Cu1 121.2(4) . 25 ? C4 C2 C3 119.7(5) . . ? C4 C2 C1 119.7(5) . . ? C3 C2 C1 120.5(5) . . ? C2 C3 C2 120.8(7) . 16 ? C2 C3 H3 119.6 . . ? C2 C3 H3 119.6 16 . ? C2 C4 C5 119.9(5) . . ? C2 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C4 119.9(8) . 16 ? C4 C5 C6 120.1(4) . . ? C4 C5 C6 120.1(4) 16 . ? C6 C6 C5 179.999(1) 31 . ? 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 O2 Cu1 O1 C1 1.6(12) 25 . . . ? O2 Cu1 O1 C1 -81.4(5) 11 . . . ? O1 Cu1 O1 C1 86.4(5) 23 . . . ? O3 Cu1 O1 C1 -179.0(5) . . . . ? Cu1 Cu1 O1 C1 3.8(5) 25 . . . ? Cu1 O1 C1 O2 -9.5(10) . . . . ? Cu1 O1 C1 C2 168.7(5) . . . . ? O1 C1 O2 Cu1 10.0(10) . . . 25 ? C2 C1 O2 Cu1 -168.2(5) . . . 25 ? O1 C1 C2 C4 -9.5(10) . . . . ? O2 C1 C2 C4 168.9(7) . . . . ? O1 C1 C2 C3 174.5(6) . . . . ? O2 C1 C2 C3 -7.1(10) . . . . ? C4 C2 C3 C2 -0.1(5) . . . 16 ? C1 C2 C3 C2 175.9(8) . . . 16 ? C3 C2 C4 C5 0.2(11) . . . . ? C1 C2 C4 C5 -175.9(6) . . . . ? C2 C4 C5 C4 -0.1(5) . . . 16 ? C2 C4 C5 C6 179.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 67.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 3.604 _refine_diff_density_min -1.156 _refine_diff_density_rms 0.204