# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Moreau, Florian' 'Audebrand, Nathalie' 'PORIEL, Cyril' _publ_contact_author_name 'Audebrand, Nathalie' _publ_contact_author_email nathalie.audebrand@univ-rennes1.fr _publ_section_title ; A 9,9'-spirobifluorene based Metal-Organic Framework: synthesis, structure analysis and gas sorption properties ; # Attachment '- Moreau_SBFCu.cif' data_squeeze _database_code_depnum_ccdc_archive 'CCDC 831047' #TrackingRef '- Moreau_SBFCu.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C53 H28 Cu2 O10' _chemical_formula_weight 475.92 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P12/c1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 13.698(5) _cell_length_b 16.631(5) _cell_length_c 14.562(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 95.825(5) _cell_angle_gamma 90.000(5) _cell_volume 3300.3(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150 _cell_measurement_reflns_used 4671 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 22.85 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.958 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 0.686 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9345 _exptl_absorpt_correction_T_max 0.9864 _exptl_absorpt_process_details ; [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; #----------------------------- Remark ------------------------------# # Tmax and Tmin values correspond to EXPECTED values calculated # # from crystal size. In the case of absorption correction performed # # with SADABS program, Tmax should be given as Tmax_expected and # # and Tmin = Tmax * 'relative-correction-factor'. # # SADABS output: # # Ratio of minimum to maximum apparent transmission: 0.822975 #-------------------------------------------------------------------# _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'APEXII, Bruker-AXS' _diffrn_measurement_method 'CCD rotation images, thin slices' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29898 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0777 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 27.62 _reflns_number_total 7600 _reflns_number_gt 4842 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SAINT (Bruker, 2002)' _computing_cell_refinement 'Bruker SMART (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT (Bruker, 2002)' _computing_structure_solution 'SIR97 (Altomare al, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Berndt, 2001)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^ > 2\s(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^)+(0.0872P)^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 7600 _refine_ls_number_parameters 294 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0789 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1504 _refine_ls_wR_factor_gt 0.1395 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 -0.45149(2) 0.476409(19) 0.07768(2) 0.02378(12) Uani 1 1 d . . . O2 O 0.38720(17) 1.39994(13) -0.50207(14) 0.0424(6) Uani 1 1 d . . . C1 C 0.0000 0.9991(2) -0.2500 0.0193(8) Uani 1 2 d S . . C2 C -0.0098(2) 0.94681(15) -0.16546(18) 0.0223(6) Uani 1 1 d . . . C15 C 0.0910(2) 1.04870(15) -0.21712(18) 0.0220(6) Uani 1 1 d . . . O6 O 0.46817(16) 1.44141(13) -0.37033(14) 0.0397(6) Uani 1 1 d . . . C3 C 0.0678(2) 0.96029(16) -0.09822(19) 0.0252(6) Uani 1 1 d . . . C8 C -0.1468(2) 0.77963(18) -0.0602(2) 0.0336(7) Uani 1 1 d . . . C16 C 0.1302(2) 1.02425(16) -0.12888(19) 0.0257(6) Uani 1 1 d . . . C4 C 0.0750(2) 0.91528(19) -0.0168(2) 0.0361(8) Uani 1 1 d . . . H4 H 0.1345 0.9265 0.0383 0.054 Uiso 1 1 calc R . . C11 C -0.2898(2) 0.66241(18) -0.0341(2) 0.0349(7) Uani 1 1 d . . . C6 C -0.0727(2) 0.84199(18) -0.0735(2) 0.0309(7) Uani 1 1 d . . . C27 C 0.4084(2) 1.39644(17) -0.4155(2) 0.0302(7) Uani 1 1 d . . . O14 O -0.35472(17) 0.55781(14) 0.05064(17) 0.0480(6) Uani 1 1 d . . . C19 C 0.2174(2) 1.14889(18) -0.2191(2) 0.0319(7) Uani 1 1 d . . . C7 C -0.0801(2) 0.88831(16) -0.15556(19) 0.0259(6) Uani 1 1 d . . . H7 H -0.1403 0.8781 -0.2102 0.039 Uiso 1 1 calc R . . C23 C 0.3658(2) 1.33327(19) -0.2686(2) 0.0394(8) Uani 1 1 d . . . H23 H 0.4088 1.3803 -0.2299 0.059 Uiso 1 1 calc R . . C17 C 0.2123(2) 1.06213(19) -0.0864(2) 0.0358(7) Uani 1 1 d . . . H17 H 0.2433 1.0435 -0.0170 0.054 Uiso 1 1 calc R . . O19 O -0.43795(17) 0.59828(13) -0.07939(16) 0.0455(6) Uani 1 1 d . . . O20 O -0.38435(19) 0.43942(17) 0.21303(16) 0.0583(7) Uani 1 1 d . . . C21 C 0.2648(2) 1.21433(18) -0.2691(2) 0.0341(7) Uani 1 1 d . . . C20 C 0.1330(2) 1.11130(16) -0.26133(19) 0.0260(6) Uani 1 1 d . . . H20 H 0.1003 1.1316 -0.3295 0.039 Uiso 1 1 calc R . . C5 C 0.0058(2) 0.85629(18) -0.0071(2) 0.0367(8) Uani 1 1 d . . . H5 H 0.0130 0.8191 0.0557 0.055 Uiso 1 1 calc R . . C24 C 0.3587(2) 1.33373(18) -0.3638(2) 0.0336(7) Uani 1 1 d . . . C13 C -0.2434(3) 0.7868(2) -0.1018(3) 0.0530(10) Uani 1 1 d . . . H13 H -0.2642 0.8395 -0.1452 0.080 Uiso 1 1 calc R . . C18 C 0.2552(2) 1.12361(19) -0.1318(2) 0.0360(8) Uani 1 1 d . . . H18 H 0.3211 1.1533 -0.0980 0.054 Uiso 1 1 calc R . . C14 C -0.3664(2) 0.60152(18) -0.0205(2) 0.0322(7) Uani 1 1 d . . . C26 C 0.2588(3) 1.2142(2) -0.3648(2) 0.0521(10) Uani 1 1 d . . . H26 H 0.2172 1.1664 -0.4037 0.078 Uiso 1 1 calc R . . C22 C 0.3199(2) 1.27504(19) -0.2210(2) 0.0403(8) Uani 1 1 d . . . H22 H 0.3264 1.2762 -0.1451 0.060 Uiso 1 1 calc R . . C25 C 0.3039(3) 1.2726(2) -0.4117(2) 0.0589(12) Uani 1 1 d . . . H25 H 0.2972 1.2716 -0.4876 0.088 Uiso 1 1 calc R . . C9 C -0.1248(3) 0.7122(2) -0.0063(3) 0.0600(12) Uani 1 1 d . . . H9 H -0.0494 0.7039 0.0261 0.090 Uiso 1 1 calc R . . C10 C -0.1949(3) 0.6552(2) 0.0080(3) 0.0577(11) Uani 1 1 d . . . H10 H -0.1752 0.6035 0.0532 0.087 Uiso 1 1 calc R . . C12 C -0.3129(3) 0.7282(2) -0.0889(3) 0.0511(10) Uani 1 1 d . . . H12 H -0.3878 0.7347 -0.1231 0.077 Uiso 1 1 calc R . . 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 0.0261(2) 0.01864(18) 0.0277(2) -0.00168(14) 0.00821(14) -0.00113(14) O2 0.0598(15) 0.0400(13) 0.0287(12) 0.0009(10) 0.0108(11) -0.0230(11) C1 0.0225(19) 0.0141(16) 0.021(2) 0.000 0.0029(16) 0.000 C2 0.0311(15) 0.0166(12) 0.0195(14) 0.0022(11) 0.0048(12) 0.0005(11) C15 0.0262(14) 0.0201(13) 0.0200(14) 0.0004(11) 0.0035(11) -0.0023(11) O6 0.0446(13) 0.0396(13) 0.0333(12) 0.0133(10) -0.0037(10) -0.0204(11) C3 0.0297(15) 0.0233(15) 0.0222(15) 0.0047(11) 0.0014(12) -0.0055(12) C8 0.0371(17) 0.0320(16) 0.0320(17) 0.0023(13) 0.0052(14) -0.0158(14) C16 0.0315(15) 0.0226(14) 0.0232(14) 0.0030(12) 0.0037(12) -0.0058(12) C4 0.0452(19) 0.0360(18) 0.0247(16) 0.0093(13) -0.0076(14) -0.0119(15) C11 0.0408(19) 0.0286(16) 0.0371(18) -0.0012(14) 0.0129(15) -0.0100(14) C6 0.0364(17) 0.0278(16) 0.0293(16) 0.0025(13) 0.0072(14) -0.0096(13) C27 0.0329(17) 0.0227(15) 0.0361(18) 0.0036(13) 0.0095(14) -0.0043(12) O14 0.0478(14) 0.0416(14) 0.0549(16) 0.0113(12) 0.0072(12) -0.0212(12) C19 0.0408(18) 0.0298(16) 0.0260(16) 0.0003(13) 0.0075(13) -0.0101(13) C7 0.0281(15) 0.0241(14) 0.0253(15) 0.0009(12) 0.0024(12) -0.0069(12) C23 0.048(2) 0.0343(18) 0.0346(18) 0.0000(14) -0.0008(15) -0.0180(15) C17 0.0385(18) 0.0400(18) 0.0270(16) 0.0057(14) -0.0054(14) -0.0152(14) O19 0.0423(14) 0.0422(14) 0.0518(15) 0.0137(11) 0.0039(12) -0.0174(11) O20 0.0660(18) 0.0757(19) 0.0342(14) 0.0119(13) 0.0092(12) 0.0254(15) C21 0.0423(18) 0.0309(16) 0.0297(17) -0.0002(13) 0.0072(14) -0.0152(14) C20 0.0335(16) 0.0238(14) 0.0212(14) -0.0002(12) 0.0053(12) -0.0084(12) C5 0.048(2) 0.0346(16) 0.0261(16) 0.0122(13) -0.0017(14) -0.0154(15) C24 0.0416(18) 0.0334(17) 0.0266(16) 0.0015(13) 0.0073(14) -0.0140(14) C13 0.052(2) 0.052(2) 0.052(2) 0.0225(19) -0.0079(18) -0.0168(18) C18 0.0369(18) 0.0395(18) 0.0300(17) 0.0097(14) -0.0037(14) -0.0162(14) C14 0.0345(18) 0.0252(16) 0.0390(18) -0.0035(14) 0.0134(15) -0.0067(13) C26 0.079(3) 0.052(2) 0.0261(18) -0.0031(16) 0.0077(17) -0.040(2) C22 0.055(2) 0.0386(18) 0.0273(17) 0.0011(14) 0.0043(15) -0.0233(16) C25 0.092(3) 0.055(2) 0.033(2) -0.0037(17) 0.0183(19) -0.042(2) C9 0.041(2) 0.056(2) 0.079(3) 0.038(2) -0.0128(19) -0.0188(18) C10 0.049(2) 0.053(2) 0.070(3) 0.033(2) -0.004(2) -0.0169(18) C12 0.042(2) 0.050(2) 0.058(2) 0.0119(18) -0.0100(18) -0.0207(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.950(2) 2_544 ? Cu1 O6 1.955(2) 4_476 ? Cu1 O19 1.961(2) 3_465 ? Cu1 O14 1.962(2) . ? Cu1 O20 2.177(2) . ? Cu1 Cu1 2.6249(10) 3_465 ? Cu1 O20 4.014(3) 2_455 ? Cu1 O20 4.796(3) 3_465 ? O2 C27 1.265(4) . ? O2 Cu1 1.950(2) 2_564 ? O2 O20 3.138(3) 2_564 ? C1 C2 1.525(3) 2_554 ? C1 C2 1.525(3) . ? C1 C15 1.530(3) . ? C1 C15 1.530(3) 2_554 ? C2 C7 1.386(4) . ? C2 C3 1.389(4) . ? C15 C20 1.380(4) . ? C15 C16 1.402(4) . ? O6 C27 1.246(3) . ? O6 Cu1 1.955(2) 4_675 ? O6 O20 2.997(3) 4_675 ? O6 O20 3.321(3) 3_575 ? C3 C4 1.397(4) . ? C3 C16 1.462(4) . ? C8 C9 1.385(4) . ? C8 C13 1.403(5) . ? C8 C6 1.478(4) . ? C16 C17 1.379(4) . ? C4 C5 1.382(4) . ? C4 H4 1.1000 . ? C11 C12 1.372(5) . ? C11 C10 1.385(5) . ? C11 C14 1.486(4) . ? C11 O20 4.140(4) 4_565 ? C6 C5 1.391(4) . ? C6 C7 1.417(4) . ? C27 C24 1.491(4) . ? C27 O20 4.056(4) 3_575 ? C27 O20 4.235(4) 4_675 ? C27 O20 4.370(4) 2_564 ? O14 C14 1.263(4) . ? O14 O20 3.135(3) . ? C19 C18 1.388(4) . ? C19 C20 1.400(4) . ? C19 C21 1.494(4) . ? C7 H7 1.1000 . ? C23 C22 1.379(4) . ? C23 C24 1.380(4) . ? C23 O20 3.869(4) 3_575 ? C23 H23 1.1000 . ? C17 C18 1.381(4) . ? C17 H17 1.1000 . ? O19 C14 1.236(4) . ? O19 Cu1 1.961(2) 3_465 ? O19 O20 3.024(4) 3_465 ? O19 O20 3.243(3) 4_565 ? O20 O6 2.997(3) 4_476 ? O20 O19 3.024(4) 3_465 ? O20 O2 3.138(3) 2_544 ? O20 O19 3.243(3) 4_566 ? O20 O6 3.321(3) 3_575 ? O20 O20 3.448(5) 2_455 ? O20 C23 3.869(4) 3_575 ? O20 C14 3.922(4) 4_566 ? C21 C26 1.388(4) . ? C21 C22 1.404(4) . ? C20 H20 1.1000 . ? C5 H5 1.1000 . ? C24 C25 1.406(4) . ? C24 O20 4.362(4) 3_575 ? C13 C12 1.389(5) . ? C13 H13 1.1000 . ? C18 H18 1.1000 . ? C14 O20 3.922(4) 4_565 ? C14 O20 4.247(4) 3_465 ? C26 C25 1.370(4) . ? C26 H26 1.1000 . ? C22 H22 1.1000 . ? C25 H25 1.1000 . ? C9 C10 1.380(5) . ? C9 H9 1.1000 . ? C10 H10 1.1000 . ? C12 O20 4.060(5) 4_565 ? C12 H12 1.1000 . ? 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 O6 168.23(9) 2_544 4_476 ? O2 Cu1 O19 89.29(11) 2_544 3_465 ? O6 Cu1 O19 88.41(11) 4_476 3_465 ? O2 Cu1 O14 89.06(11) 2_544 . ? O6 Cu1 O14 90.78(11) 4_476 . ? O19 Cu1 O14 167.93(10) 3_465 . ? O2 Cu1 O20 98.82(9) 2_544 . ? O6 Cu1 O20 92.84(9) 4_476 . ? O19 Cu1 O20 93.75(10) 3_465 . ? O14 Cu1 O20 98.32(11) . . ? O2 Cu1 Cu1 85.78(7) 2_544 3_465 ? O6 Cu1 Cu1 82.48(7) 4_476 3_465 ? O19 Cu1 Cu1 82.89(7) 3_465 3_465 ? O14 Cu1 Cu1 85.07(7) . 3_465 ? O20 Cu1 Cu1 174.29(7) . 3_465 ? O2 Cu1 O20 130.44(8) 2_544 2_455 ? O6 Cu1 O20 55.42(8) 4_476 2_455 ? O19 Cu1 O20 53.16(8) 3_465 2_455 ? O14 Cu1 O20 134.42(8) . 2_455 ? O20 Cu1 O20 59.15(10) . 2_455 ? Cu1 Cu1 O20 115.25(5) 3_465 2_455 ? O2 Cu1 O20 83.69(7) 2_544 3_465 ? O6 Cu1 O20 84.60(7) 4_476 3_465 ? O19 Cu1 O20 84.41(8) 3_465 3_465 ? O14 Cu1 O20 83.53(8) . 3_465 ? O20 Cu1 O20 176.88(4) . 3_465 ? Cu1 Cu1 O20 2.59(3) 3_465 3_465 ? O20 Cu1 O20 117.79(7) 2_455 3_465 ? C27 O2 Cu1 121.39(19) . 2_564 ? C27 O2 O20 164.42(19) . 2_564 ? Cu1 O2 O20 43.29(6) 2_564 2_564 ? C2 C1 C2 110.4(3) 2_554 . ? C2 C1 C15 115.11(14) 2_554 . ? C2 C1 C15 101.00(14) . . ? C2 C1 C15 101.00(14) 2_554 2_554 ? C2 C1 C15 115.11(14) . 2_554 ? C15 C1 C15 114.8(3) . 2_554 ? C7 C2 C3 122.0(2) . . ? C7 C2 C1 127.1(2) . . ? C3 C2 C1 110.7(2) . . ? C20 C15 C16 120.5(3) . . ? C20 C15 C1 128.7(2) . . ? C16 C15 C1 110.8(2) . . ? C27 O6 Cu1 125.5(2) . 4_675 ? C27 O6 O20 172.0(2) . 4_675 ? Cu1 O6 O20 46.51(7) 4_675 4_675 ? C27 O6 O20 117.9(2) . 3_575 ? Cu1 O6 O20 95.60(9) 4_675 3_575 ? O20 O6 O20 65.92(11) 4_675 3_575 ? C2 C3 C4 119.6(3) . . ? C2 C3 C16 109.4(2) . . ? C4 C3 C16 131.0(3) . . ? C9 C8 C13 117.1(3) . . ? C9 C8 C6 121.9(3) . . ? C13 C8 C6 120.9(3) . . ? C17 C16 C15 119.9(3) . . ? C17 C16 C3 132.1(3) . . ? C15 C16 C3 108.0(2) . . ? C5 C4 C3 118.5(3) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C12 C11 C10 118.5(3) . . ? C12 C11 C14 119.8(3) . . ? C10 C11 C14 121.7(3) . . ? C12 C11 O20 77.1(2) . 4_565 ? C10 C11 O20 123.6(3) . 4_565 ? C14 C11 O20 71.23(17) . 4_565 ? C5 C6 C7 118.5(3) . . ? C5 C6 C8 121.4(3) . . ? C7 C6 C8 120.0(3) . . ? O6 C27 O2 124.8(3) . . ? O6 C27 C24 117.5(3) . . ? O2 C27 C24 117.7(3) . . ? O6 C27 O20 46.34(17) . 3_575 ? O2 C27 O20 131.7(2) . 3_575 ? C24 C27 O20 91.64(17) . 3_575 ? O6 C27 O20 5.68(14) . 4_675 ? O2 C27 O20 119.11(18) . 4_675 ? C24 C27 O20 123.21(19) . 4_675 ? O20 C27 O20 49.09(8) 3_575 4_675 ? O6 C27 O20 113.89(18) . 2_564 ? O2 C27 O20 11.12(14) . 2_564 ? C24 C27 O20 128.52(19) . 2_564 ? O20 C27 O20 127.38(7) 3_575 2_564 ? O20 C27 O20 108.21(7) 4_675 2_564 ? C14 O14 Cu1 122.0(2) . . ? C14 O14 O20 164.9(2) . . ? Cu1 O14 O20 43.41(7) . . ? C18 C19 C20 118.8(3) . . ? C18 C19 C21 121.7(3) . . ? C20 C19 C21 119.4(3) . . ? C2 C7 C6 118.6(3) . . ? C2 C7 H7 120.7 . . ? C6 C7 H7 120.7 . . ? C22 C23 C24 121.3(3) . . ? C22 C23 O20 127.2(2) . 3_575 ? C24 C23 O20 101.6(2) . 3_575 ? C22 C23 H23 119.3 . . ? C24 C23 H23 119.3 . . ? O20 C23 H23 34.7 3_575 . ? C16 C17 C18 119.4(3) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C14 O19 Cu1 125.3(2) . 3_465 ? C14 O19 O20 170.1(2) . 3_465 ? Cu1 O19 O20 45.93(7) 3_465 3_465 ? C14 O19 O20 114.6(2) . 4_565 ? Cu1 O19 O20 97.90(10) 3_465 4_565 ? O20 O19 O20 66.65(9) 3_465 4_565 ? Cu1 O20 O6 40.64(6) . 4_476 ? Cu1 O20 O19 40.32(6) . 3_465 ? O6 O20 O19 53.92(8) 4_476 3_465 ? Cu1 O20 O14 38.27(6) . . ? O6 O20 O14 54.04(8) 4_476 . ? O19 O20 O14 78.59(8) 3_465 . ? Cu1 O20 O2 37.89(6) . 2_544 ? O6 O20 O2 78.52(8) 4_476 2_544 ? O19 O20 O2 52.94(8) 3_465 2_544 ? O14 O20 O2 51.88(7) . 2_544 ? Cu1 O20 O19 141.58(11) . 4_566 ? O6 O20 O19 107.35(9) 4_476 4_566 ? O19 O20 O19 108.43(10) 3_465 4_566 ? O14 O20 O19 152.04(11) . 4_566 ? O2 O20 O19 152.93(12) 2_544 4_566 ? Cu1 O20 O6 108.17(10) . 3_575 ? O6 O20 O6 67.59(9) 4_476 3_575 ? O19 O20 O6 104.81(10) 3_465 3_575 ? O14 O20 O6 103.05(10) . 3_575 ? O2 O20 O6 146.04(10) 2_544 3_575 ? O19 O20 O6 49.13(6) 4_566 3_575 ? Cu1 O20 O20 88.03(11) . 2_455 ? O6 O20 O20 61.55(8) 4_476 2_455 ? O19 O20 O20 59.72(9) 3_465 2_455 ? O14 O20 O20 115.40(9) . 2_455 ? O2 O20 O20 112.66(11) 2_544 2_455 ? O19 O20 O20 53.62(7) 4_566 2_455 ? O6 O20 O20 52.53(6) 3_575 2_455 ? Cu1 O20 C23 85.76(9) . 3_575 ? O6 O20 C23 57.72(8) 4_476 3_575 ? O19 O20 C23 111.64(9) 3_465 3_575 ? O14 O20 C23 62.18(8) . 3_575 ? O2 O20 C23 113.78(9) 2_544 3_575 ? O19 O20 C23 90.59(9) 4_566 3_575 ? O6 O20 C23 44.97(7) 3_575 3_575 ? O20 O20 C23 88.72(7) 2_455 3_575 ? Cu1 O20 C14 157.33(11) . 4_566 ? O6 O20 C14 119.17(9) 4_476 4_566 ? O19 O20 C14 124.48(10) 3_465 4_566 ? O14 O20 C14 148.79(11) . 4_566 ? O2 O20 C14 157.73(10) 2_544 4_566 ? O19 O20 C14 16.65(6) 4_566 4_566 ? O6 O20 C14 54.03(7) 3_575 4_566 ? O20 O20 C14 70.03(9) 2_455 4_566 ? C23 O20 C14 88.08(8) 3_575 4_566 ? C26 C21 C22 118.4(3) . . ? C26 C21 C19 120.3(3) . . ? C22 C21 C19 121.3(3) . . ? C15 C20 C19 119.8(3) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C4 C5 C6 122.7(3) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C23 C24 C25 118.2(3) . . ? C23 C24 C27 121.5(3) . . ? C25 C24 C27 120.3(3) . . ? C23 C24 O20 60.33(18) . 3_575 ? C25 C24 O20 152.5(3) . 3_575 ? C27 C24 O20 68.38(16) . 3_575 ? C12 C13 C8 120.7(3) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C17 C18 C19 121.7(3) . . ? C17 C18 H18 119.2 . . ? C19 C18 H18 119.2 . . ? O19 C14 O14 124.7(3) . . ? O19 C14 C11 117.3(3) . . ? O14 C14 C11 118.0(3) . . ? O19 C14 O20 48.75(17) . 4_565 ? O14 C14 O20 134.6(2) . 4_565 ? C11 C14 O20 87.74(18) . 4_565 ? O19 C14 O20 7.01(15) . 3_465 ? O14 C14 O20 118.42(19) . 3_465 ? C11 C14 O20 123.6(2) . 3_465 ? O20 C14 O20 49.74(8) 4_565 3_465 ? O19 C14 O20 114.20(19) . . ? O14 C14 O20 10.81(15) . . ? C11 C14 O20 128.4(2) . . ? O20 C14 O20 131.34(8) 4_565 . ? O20 C14 O20 108.07(7) 3_465 . ? C25 C26 C21 121.1(3) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? C23 C22 C21 120.2(3) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C26 C25 C24 120.7(3) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C10 C9 C8 121.8(3) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 120.6(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C11 C12 C13 121.2(3) . . ? C11 C12 O20 83.7(2) . 4_565 ? C13 C12 O20 120.3(3) . 4_565 ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? O20 C12 H12 66.3 4_565 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C23 H23 O6 1.10 2.49 2.796(4) 94.2 . _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.455 _refine_diff_density_min -0.524 _refine_diff_density_rms 0.104