# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Juan Cuerva' _publ_contact_author_email jmcuerva@ugr.es _publ_section_title ; on/off Electrochemical switches based on quinone-bisketals ; loop_ _publ_author_name 'Noelia Fuentes' 'Andres Parra' 'Luis Alvarez de Cienfuegos' S.Rodriguez-Bolivar F.M.Gomez-Campos 'Duane Choquesillo-Lazarte' 'Juan Manuel Garcia-Ruiz' 'M. Luisa Marcos' E.Bunuel 'Maria Ribagorda' 'M Carmen Carreno' D.J.Cardenas J.M.Cuerva # Attachment '- Compounds.cif' data_compound1 _database_code_depnum_ccdc_archive 'CCDC 750177' #TrackingRef '- Compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H18 O2' _chemical_formula_sum 'C20 H18 O2' _chemical_formula_weight 290.34 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 5.8194(3) _cell_length_b 18.0195(8) _cell_length_c 7.6388(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.028(2) _cell_angle_gamma 90.00 _cell_volume 788.79(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4177 _cell_measurement_theta_min 6.38 _cell_measurement_theta_max 65.65 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.613 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8618 _exptl_absorpt_correction_T_max 0.9301 _exptl_absorpt_process_details 'SADABS in APEX2, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator 'graded multilayer optics' _diffrn_measurement_device_type 'Bruker X8 Proteum' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6521 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 6.38 _diffrn_reflns_theta_max 66.45 _reflns_number_total 1275 _reflns_number_gt 1202 _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 ? _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^)+(0.0702P)^2^+0.1590P] 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 1275 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1258 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.004 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 -0.0452(3) 0.43738(9) 0.7209(2) 0.0630(5) Uani 1 1 d . . . H1A H 0.0401 0.3920 0.7167 0.094 Uiso 1 1 calc R . . H1B H -0.1593 0.4422 0.6145 0.094 Uiso 1 1 calc R . . H1C H -0.1222 0.4367 0.8223 0.094 Uiso 1 1 calc R . . O2 O 0.1106(2) 0.49812(6) 0.73463(15) 0.0673(4) Uani 1 1 d . . . C3 C 0.3008(2) 0.49761(7) 0.86886(18) 0.0470(4) Uani 1 1 d . . . C4 C 0.4611(2) 0.55535(7) 0.86851(17) 0.0442(4) Uani 1 1 d . . . C5 C 0.6587(2) 0.55667(8) 1.00052(18) 0.0482(4) Uani 1 1 d . . . H5 H 0.7663 0.5949 1.0012 0.058 Uiso 1 1 calc R . . C6 C 0.4234(2) 0.61449(7) 0.72922(17) 0.0450(4) Uani 1 1 d . . . C7 C 0.2351(3) 0.66177(8) 0.7153(2) 0.0558(4) Uani 1 1 d . . . H7 H 0.1306 0.6569 0.7939 0.067 Uiso 1 1 calc R . . C8 C 0.1986(3) 0.71655(9) 0.5860(2) 0.0605(5) Uani 1 1 d . . . H8 H 0.0713 0.7483 0.5792 0.073 Uiso 1 1 calc R . . C9 C 0.3498(3) 0.72396(9) 0.4684(2) 0.0608(5) Uani 1 1 d . . . H9 H 0.3244 0.7600 0.3801 0.073 Uiso 1 1 calc R . . C10 C 0.5392(3) 0.67762(10) 0.4821(2) 0.0687(5) Uani 1 1 d . . . H10 H 0.6431 0.6828 0.4032 0.082 Uiso 1 1 calc R . . C11 C 0.5773(3) 0.62331(9) 0.6120(2) 0.0585(5) Uani 1 1 d . . . H11 H 0.7072 0.5926 0.6205 0.070 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 C1 0.0610(10) 0.0622(10) 0.0593(9) -0.0044(7) -0.0076(7) -0.0114(7) O2 0.0662(8) 0.0654(7) 0.0600(7) 0.0146(5) -0.0179(5) -0.0170(5) C3 0.0498(8) 0.0492(8) 0.0389(7) 0.0014(5) -0.0010(6) -0.0029(6) C4 0.0507(8) 0.0428(7) 0.0380(7) 0.0014(5) 0.0047(5) -0.0001(5) C5 0.0520(8) 0.0455(8) 0.0451(8) 0.0026(5) 0.0028(6) -0.0081(6) C6 0.0505(8) 0.0435(8) 0.0389(7) -0.0003(5) 0.0016(5) -0.0044(5) C7 0.0660(10) 0.0525(9) 0.0507(8) 0.0040(6) 0.0151(7) 0.0067(7) C8 0.0677(10) 0.0487(9) 0.0634(10) 0.0052(7) 0.0063(7) 0.0109(7) C9 0.0707(10) 0.0518(9) 0.0570(9) 0.0177(7) 0.0028(7) -0.0028(7) C10 0.0660(11) 0.0772(11) 0.0660(10) 0.0251(8) 0.0202(8) 0.0016(8) C11 0.0531(9) 0.0618(9) 0.0615(9) 0.0158(7) 0.0121(7) 0.0061(7) _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 O2 1.4133(19) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? O2 C3 1.3714(18) . ? C3 C5 1.3879(19) 3_667 ? C3 C4 1.3977(19) . ? C4 C5 1.3916(19) . ? C4 C6 1.4948(18) . ? C5 C3 1.3879(19) 3_667 ? C5 H5 0.9300 . ? C6 C7 1.378(2) . ? C6 C11 1.381(2) . ? C7 C8 1.386(2) . ? C7 H7 0.9300 . ? C8 C9 1.369(3) . ? C8 H8 0.9300 . ? C9 C10 1.372(2) . ? C9 H9 0.9300 . ? C10 C11 1.384(2) . ? C10 H10 0.9300 . ? C11 H11 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 118.29(11) . . ? O2 C3 C5 123.79(12) . 3_667 ? O2 C3 C4 116.46(12) . . ? C5 C3 C4 119.75(13) 3_667 . ? C5 C4 C3 118.62(12) . . ? C5 C4 C6 120.26(12) . . ? C3 C4 C6 121.11(12) . . ? C4 C5 C3 121.63(13) . 3_667 ? C4 C5 H5 119.2 . . ? C3 C5 H5 119.2 3_667 . ? C7 C6 C11 118.40(13) . . ? C7 C6 C4 120.81(12) . . ? C11 C6 C4 120.79(13) . . ? C6 C7 C8 121.12(14) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C9 C8 C7 120.03(15) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 119.34(14) . . ? C8 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C9 C10 C11 120.77(15) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? C6 C11 C10 120.32(15) . . ? C6 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 66.45 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.209 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.026 data_compound1a _database_code_depnum_ccdc_archive 'CCDC 750178' #TrackingRef '- Compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H24 O4' _chemical_formula_sum 'C22 H24 O4' _chemical_formula_weight 352.41 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.4349(7) _cell_length_b 17.3703(19) _cell_length_c 8.4716(9) _cell_angle_alpha 90.00 _cell_angle_beta 110.133(3) _cell_angle_gamma 90.00 _cell_volume 889.06(17) _cell_formula_units_Z 2 _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 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.722 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.8458 _exptl_absorpt_correction_T_max 0.8871 _exptl_absorpt_process_details 'SADABS in APEX2, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator 'graded multilayer optics' _diffrn_measurement_device_type 'Bruker X8 Proteum' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8382 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 10.23 _diffrn_reflns_theta_max 66.53 _reflns_number_total 1463 _reflns_number_gt 1443 _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 ? _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^)+(0.0392P)^2^+0.3841P] 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 1463 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 C1 C 0.2454(2) 0.17086(8) 0.30744(17) 0.0249(3) Uani 1 1 d . . . H1 H 0.3530 0.1678 0.2541 0.030 Uiso 1 1 calc R . . C2 C 0.2684(2) 0.22557(8) 0.43204(18) 0.0288(4) Uani 1 1 d . . . H2 H 0.3919 0.2594 0.4631 0.035 Uiso 1 1 calc R . . C3 C 0.1134(3) 0.23133(8) 0.51152(17) 0.0285(4) Uani 1 1 d . . . H3 H 0.1291 0.2693 0.5956 0.034 Uiso 1 1 calc R . . C4 C -0.0648(2) 0.18106(8) 0.46676(17) 0.0268(4) Uani 1 1 d . . . H4 H -0.1718 0.1846 0.5207 0.032 Uiso 1 1 calc R . . C5 C -0.0884(2) 0.12566(8) 0.34410(16) 0.0232(3) Uani 1 1 d . . . H5 H -0.2096 0.0909 0.3167 0.028 Uiso 1 1 calc R . . C6 C 0.0647(2) 0.12022(7) 0.25970(15) 0.0199(3) Uani 1 1 d . . . C7 C 0.0301(2) 0.06139(7) 0.12463(15) 0.0187(3) Uani 1 1 d . . . C8 C 0.2287(2) 0.02921(7) 0.08819(16) 0.0193(3) Uani 1 1 d . . . C9 C 0.1729(2) -0.03604(7) -0.03566(15) 0.0199(3) Uani 1 1 d . . . H9 H 0.2937 -0.0619 -0.0525 0.024 Uiso 1 1 calc R . . O10 O 0.33734(14) 0.08855(5) 0.02784(11) 0.0231(3) Uani 1 1 d . . . C11 C 0.2216(2) 0.11658(8) -0.13683(17) 0.0260(3) Uani 1 1 d . . . H11A H 0.1989 0.0744 -0.2179 0.039 Uiso 1 1 calc R . . H11B H 0.3085 0.1574 -0.1645 0.039 Uiso 1 1 calc R . . H11C H 0.0779 0.1372 -0.1416 0.039 Uiso 1 1 calc R . . O12 O 0.40412(14) 0.00866(5) 0.23765(11) 0.0226(3) Uani 1 1 d . . . C13 C 0.3546(2) -0.05413(8) 0.32672(17) 0.0292(4) Uani 1 1 d . . . H13A H 0.2286 -0.0406 0.3611 0.044 Uiso 1 1 calc R . . H13B H 0.4837 -0.0654 0.4266 0.044 Uiso 1 1 calc R . . H13C H 0.3175 -0.0996 0.2538 0.044 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 C1 0.0245(7) 0.0254(7) 0.0236(7) -0.0011(5) 0.0069(5) -0.0008(5) C2 0.0311(8) 0.0236(7) 0.0272(7) -0.0026(5) 0.0041(6) -0.0038(6) C3 0.0399(8) 0.0236(7) 0.0195(7) -0.0029(5) 0.0067(6) 0.0028(6) C4 0.0328(8) 0.0285(7) 0.0205(7) 0.0007(5) 0.0111(6) 0.0043(6) C5 0.0243(7) 0.0247(7) 0.0201(7) 0.0010(5) 0.0070(5) 0.0005(5) C6 0.0209(7) 0.0203(6) 0.0165(6) 0.0028(5) 0.0040(5) 0.0028(5) C7 0.0197(6) 0.0193(6) 0.0175(6) 0.0027(5) 0.0071(5) 0.0012(5) C8 0.0158(6) 0.0224(7) 0.0192(6) 0.0008(5) 0.0053(5) -0.0008(5) C9 0.0184(7) 0.0222(7) 0.0196(6) 0.0003(5) 0.0073(5) 0.0022(5) O10 0.0195(5) 0.0279(5) 0.0221(5) -0.0002(4) 0.0074(4) -0.0041(4) C11 0.0266(7) 0.0272(7) 0.0241(7) 0.0028(5) 0.0086(6) -0.0013(5) O12 0.0174(5) 0.0267(5) 0.0204(5) 0.0003(4) 0.0023(4) 0.0005(4) C13 0.0307(8) 0.0286(7) 0.0234(7) 0.0031(6) 0.0033(6) -0.0006(6) _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 1.390(2) . ? C1 C6 1.4018(19) . ? C1 H1 0.9500 . ? C2 C3 1.386(2) . ? C2 H2 0.9500 . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.3859(19) . ? C4 H4 0.9500 . ? C5 C6 1.4056(18) . ? C5 H5 0.9500 . ? C6 C7 1.4925(18) . ? C7 C9 1.3377(19) 3 ? C7 C8 1.5212(17) . ? C8 O12 1.4215(16) . ? C8 O10 1.4346(15) . ? C8 C9 1.5017(18) . ? C9 C7 1.3377(19) 3 ? C9 H9 0.9500 . ? O10 C11 1.4222(16) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? O12 C13 1.4233(17) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 C6 120.63(13) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C3 C2 C1 120.79(13) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 119.19(13) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.60(13) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.88(13) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 117.89(12) . . ? C1 C6 C7 122.77(12) . . ? C5 C6 C7 119.34(11) . . ? C9 C7 C6 121.11(11) 3 . ? C9 C7 C8 119.36(12) 3 . ? C6 C7 C8 119.52(11) . . ? O12 C8 O10 99.39(9) . . ? O12 C8 C9 111.00(10) . . ? O10 C8 C9 108.79(10) . . ? O12 C8 C7 112.12(10) . . ? O10 C8 C7 110.79(10) . . ? C9 C8 C7 113.79(11) . . ? C7 C9 C8 126.48(12) 3 . ? C7 C9 H9 116.8 3 . ? C8 C9 H9 116.8 . . ? C11 O10 C8 116.15(10) . . ? O10 C11 H11A 109.5 . . ? O10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C8 O12 C13 114.25(10) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 66.53 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.185 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.036 data_compound2a _database_code_depnum_ccdc_archive 'CCDC 750180' #TrackingRef '- Compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H24 O4' _chemical_formula_sum 'C26 H24 O4' _chemical_formula_weight 400.45 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.786(2) _cell_length_b 12.3380(18) _cell_length_c 16.619(3) _cell_angle_alpha 87.87(2) _cell_angle_beta 80.36(3) _cell_angle_gamma 86.62(3) _cell_volume 2175.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(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 1.223 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.75130 _diffrn_source synchrotron _diffrn_source_type 'ESRF-CRG BM16' _diffrn_radiation_monochromator 'Si 111' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9.6 _diffrn_radiation_detector 'ADSC Q210r CCD (binned mode)' _diffrn_measurement_device_type 'Single-axis HUBER diffractometer' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_number 7243 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 26.75 _reflns_number_total 7243 _reflns_number_gt 6580 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MxCube (ESRF, 2006)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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^)+(0.0921P)^2^+0.7334P] 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 7243 _refine_ls_number_parameters 549 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1462 _refine_ls_wR_factor_gt 0.1421 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.35279(16) -0.30382(13) -0.03994(10) 0.0327(4) Uani 1 1 d . . . H1 H 0.4278 -0.2814 -0.0241 0.039 Uiso 1 1 calc R . . C2 C 0.36002(18) -0.37492(13) -0.10289(11) 0.0381(4) Uani 1 1 d . . . H2 H 0.4399 -0.4017 -0.1301 0.046 Uiso 1 1 calc R . . C3 C 0.25136(19) -0.40727(14) -0.12645(11) 0.0406(4) Uani 1 1 d . . . H3 H 0.2566 -0.4566 -0.1696 0.049 Uiso 1 1 calc R . . C4 C 0.13482(19) -0.36795(15) -0.08731(12) 0.0434(4) Uani 1 1 d . . . H4 H 0.0602 -0.3897 -0.1040 0.052 Uiso 1 1 calc R . . C5 C 0.12680(16) -0.29693(13) -0.02376(11) 0.0348(4) Uani 1 1 d . . . H5 H 0.0466 -0.2704 0.0031 0.042 Uiso 1 1 calc R . . C6 C 0.23539(15) -0.26442(11) 0.00085(9) 0.0265(3) Uani 1 1 d . . . C7 C 0.22846(14) -0.19491(11) 0.06886(9) 0.0260(3) Uani 1 1 d . . . C8 C 0.22520(14) -0.14046(11) 0.12770(10) 0.0265(3) Uani 1 1 d . . . C9 C 0.22754(14) -0.07673(11) 0.19738(9) 0.0250(3) Uani 1 1 d . . . C10 C 0.10100(14) -0.04144(11) 0.24692(10) 0.0265(3) Uani 1 1 d . . . O11 O 0.04430(10) -0.13924(8) 0.27486(7) 0.0310(3) Uani 1 1 d . . . C12 C -0.07668(17) -0.12696(14) 0.32629(11) 0.0403(4) Uani 1 1 d . . . H12A H -0.0654 -0.1075 0.3811 0.060 Uiso 1 1 calc R . . H12B H -0.1190 -0.1955 0.3295 0.060 Uiso 1 1 calc R . . H12C H -0.1281 -0.0695 0.3033 0.060 Uiso 1 1 calc R . . O13 O 0.02109(10) 0.01035(8) 0.19584(7) 0.0299(3) Uani 1 1 d . . . C14 C 0.06261(16) 0.11096(12) 0.15780(11) 0.0334(4) Uani 1 1 d . . . H14A H 0.0691 0.1629 0.1999 0.050 Uiso 1 1 calc R . . H14B H 0.0019 0.1404 0.1238 0.050 Uiso 1 1 calc R . . H14C H 0.1452 0.0985 0.1236 0.050 Uiso 1 1 calc R . . C15 C 0.11360(15) 0.03062(11) 0.31555(10) 0.0277(3) Uani 1 1 d . . . H15 H 0.0381 0.0588 0.3476 0.033 Uiso 1 1 calc R . . C16 C 0.22205(15) 0.05828(11) 0.33512(9) 0.0267(3) Uani 1 1 d . . . C17 C 0.34858(14) 0.01583(11) 0.28974(9) 0.0263(3) Uani 1 1 d . . . C18 C 0.33603(14) -0.04951(11) 0.21713(9) 0.0261(3) Uani 1 1 d . . . H18 H 0.4114 -0.0732 0.1827 0.031 Uiso 1 1 calc R . . O19 O 0.42926(10) 0.10218(8) 0.26461(7) 0.0302(3) Uani 1 1 d . . . C20 C 0.38526(17) 0.17970(13) 0.20872(11) 0.0366(4) Uani 1 1 d . . . H20A H 0.3853 0.1454 0.1565 0.055 Uiso 1 1 calc R . . H20B H 0.4408 0.2406 0.2002 0.055 Uiso 1 1 calc R . . H20C H 0.2995 0.2064 0.2310 0.055 Uiso 1 1 calc R . . O21 O 0.40496(11) -0.04579(9) 0.34773(7) 0.0321(3) Uani 1 1 d . . . C22 C 0.52194(17) -0.10357(13) 0.31630(11) 0.0379(4) Uani 1 1 d . . . H22A H 0.5044 -0.1722 0.2936 0.057 Uiso 1 1 calc R . . H22B H 0.5707 -0.1187 0.3605 0.057 Uiso 1 1 calc R . . H22C H 0.5702 -0.0592 0.2734 0.057 Uiso 1 1 calc R . . C23 C 0.22636(15) 0.13215(12) 0.39880(10) 0.0290(3) Uani 1 1 d . . . C24 C 0.23000(15) 0.19891(12) 0.44886(10) 0.0287(3) Uani 1 1 d . . . C25 C 0.23152(15) 0.28127(12) 0.50722(9) 0.0280(3) Uani 1 1 d . . . C26 C 0.12742(16) 0.35512(12) 0.52592(10) 0.0305(3) Uani 1 1 d . . . H26 H 0.0557 0.3501 0.5002 0.037 Uiso 1 1 calc R . . C27 C 0.12917(17) 0.43504(13) 0.58159(10) 0.0359(4) Uani 1 1 d . . . H27 H 0.0589 0.4853 0.5938 0.043 Uiso 1 1 calc R . . C28 C 0.23305(18) 0.44233(13) 0.61982(11) 0.0391(4) Uani 1 1 d . . . H28 H 0.2332 0.4969 0.6587 0.047 Uiso 1 1 calc R . . C29 C 0.33652(18) 0.37049(14) 0.60156(11) 0.0375(4) Uani 1 1 d . . . H29 H 0.4077 0.3758 0.6277 0.045 Uiso 1 1 calc R . . C30 C 0.33612(16) 0.29077(13) 0.54496(10) 0.0319(4) Uani 1 1 d . . . H30 H 0.4078 0.2422 0.5318 0.038 Uiso 1 1 calc R . . C31 C -0.1491(2) 0.20130(15) 0.43544(12) 0.0465(5) Uani 1 1 d . . . H31 H -0.0935 0.2177 0.4715 0.056 Uiso 1 1 calc R . . C32 C -0.2501(2) 0.13679(17) 0.46278(14) 0.0627(7) Uani 1 1 d . . . H32 H -0.2634 0.1089 0.5174 0.075 Uiso 1 1 calc R . . C33 C -0.3309(2) 0.11346(16) 0.41050(17) 0.0610(7) Uani 1 1 d . . . H33 H -0.4008 0.0707 0.4296 0.073 Uiso 1 1 calc R . . C34 C -0.31095(18) 0.15160(16) 0.33072(17) 0.0560(6) Uani 1 1 d . . . H34 H -0.3660 0.1339 0.2947 0.067 Uiso 1 1 calc R . . C35 C -0.21081(16) 0.21562(13) 0.30301(14) 0.0419(4) Uani 1 1 d . . . H35 H -0.1974 0.2419 0.2480 0.050 Uiso 1 1 calc R . . C36 C -0.12956(15) 0.24180(12) 0.35518(10) 0.0304(4) Uani 1 1 d . . . C37 C -0.02486(14) 0.30720(11) 0.32551(10) 0.0272(3) Uani 1 1 d . . . C38 C 0.06355(14) 0.36053(11) 0.29913(9) 0.0260(3) Uani 1 1 d . . . C39 C 0.16859(14) 0.42437(11) 0.26793(9) 0.0248(3) Uani 1 1 d . . . C40 C 0.18311(14) 0.45710(11) 0.17780(9) 0.0254(3) Uani 1 1 d . . . O41 O 0.06901(10) 0.50652(8) 0.15880(7) 0.0300(3) Uani 1 1 d . . . C42 C 0.03051(16) 0.60826(12) 0.19598(11) 0.0341(4) Uani 1 1 d . . . H42A H 0.0158 0.5980 0.2555 0.051 Uiso 1 1 calc R . . H42B H -0.0474 0.6369 0.1781 0.051 Uiso 1 1 calc R . . H42C H 0.0967 0.6597 0.1798 0.051 Uiso 1 1 calc R . . O43 O 0.20090(11) 0.35852(8) 0.13618(6) 0.0298(3) Uani 1 1 d . . . C44 C 0.22362(18) 0.36806(14) 0.04886(10) 0.0384(4) Uani 1 1 d . . . H44A H 0.1663 0.4250 0.0309 0.058 Uiso 1 1 calc R . . H44B H 0.2092 0.2988 0.0259 0.058 Uiso 1 1 calc R . . H44C H 0.3109 0.3869 0.0300 0.058 Uiso 1 1 calc R . . C45 C 0.28875(14) 0.53119(11) 0.15156(10) 0.0266(3) Uani 1 1 d . . . H45 H 0.3002 0.5586 0.0968 0.032 Uiso 1 1 calc R . . C46 C 0.36763(14) 0.56151(11) 0.19909(9) 0.0252(3) Uani 1 1 d . . . C47 C 0.36183(14) 0.51916(11) 0.28635(9) 0.0259(3) Uani 1 1 d . . . C48 C 0.24841(14) 0.45402(11) 0.31521(9) 0.0255(3) Uani 1 1 d . . . H48 H 0.2325 0.4324 0.3713 0.031 Uiso 1 1 calc R . . O49 O 0.36485(10) 0.60569(8) 0.34026(7) 0.0307(3) Uani 1 1 d . . . C50 C 0.25845(17) 0.68110(13) 0.34649(12) 0.0392(4) Uani 1 1 d . . . H50A H 0.2467 0.7074 0.2917 0.059 Uiso 1 1 calc R . . H50B H 0.2724 0.7426 0.3790 0.059 Uiso 1 1 calc R . . H50C H 0.1831 0.6451 0.3730 0.059 Uiso 1 1 calc R . . O51 O 0.47587(10) 0.45749(9) 0.28633(7) 0.0301(3) Uani 1 1 d . . . C52 C 0.48680(17) 0.39659(13) 0.36022(11) 0.0367(4) Uani 1 1 d . . . H52A H 0.4560 0.4421 0.4073 0.055 Uiso 1 1 calc R . . H52B H 0.5753 0.3736 0.3604 0.055 Uiso 1 1 calc R . . H52C H 0.4366 0.3324 0.3635 0.055 Uiso 1 1 calc R . . C53 C 0.46292(14) 0.63618(12) 0.17022(9) 0.0271(3) Uani 1 1 d . . . C54 C 0.53916(14) 0.70182(11) 0.14629(9) 0.0266(3) Uani 1 1 d . . . C55 C 0.62847(14) 0.78232(11) 0.11896(10) 0.0268(3) Uani 1 1 d . . . C56 C 0.60377(15) 0.86241(12) 0.06124(10) 0.0309(4) Uani 1 1 d . . . H56 H 0.5281 0.8628 0.0390 0.037 Uiso 1 1 calc R . . C57 C 0.68928(17) 0.94109(13) 0.03642(11) 0.0398(4) Uani 1 1 d . . . H57 H 0.6719 0.9959 -0.0025 0.048 Uiso 1 1 calc R . . C58 C 0.80049(18) 0.94027(14) 0.06813(12) 0.0440(5) Uani 1 1 d . . . H58 H 0.8591 0.9944 0.0507 0.053 Uiso 1 1 calc R . . C59 C 0.82633(17) 0.86127(15) 0.12483(12) 0.0408(4) Uani 1 1 d . . . H59 H 0.9028 0.8607 0.1461 0.049 Uiso 1 1 calc R . . C60 C 0.74038(15) 0.78266(13) 0.15065(11) 0.0331(4) Uani 1 1 d . . . H60 H 0.7578 0.7288 0.1901 0.040 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 C1 0.0364(8) 0.0282(8) 0.0334(9) -0.0062(6) -0.0048(7) 0.0002(6) C2 0.0508(10) 0.0277(8) 0.0334(9) -0.0065(7) -0.0005(8) 0.0027(7) C3 0.0649(12) 0.0273(8) 0.0309(9) -0.0093(7) -0.0103(9) -0.0012(8) C4 0.0531(11) 0.0386(10) 0.0439(10) -0.0100(8) -0.0197(9) -0.0077(8) C5 0.0380(9) 0.0314(8) 0.0370(9) -0.0061(7) -0.0117(8) 0.0017(7) C6 0.0369(8) 0.0169(7) 0.0261(7) -0.0013(5) -0.0070(7) 0.0010(6) C7 0.0316(8) 0.0174(7) 0.0294(8) -0.0011(6) -0.0063(7) 0.0006(6) C8 0.0303(7) 0.0175(7) 0.0312(8) -0.0014(6) -0.0042(7) 0.0015(6) C9 0.0337(8) 0.0142(6) 0.0268(8) -0.0027(5) -0.0051(7) 0.0032(5) C10 0.0305(8) 0.0173(7) 0.0318(8) -0.0032(6) -0.0052(7) 0.0002(6) O11 0.0345(6) 0.0203(5) 0.0363(6) -0.0035(4) 0.0007(5) -0.0030(4) C12 0.0403(9) 0.0351(9) 0.0415(10) -0.0041(7) 0.0069(8) -0.0063(7) O13 0.0325(6) 0.0204(5) 0.0381(6) -0.0029(4) -0.0100(5) 0.0012(4) C14 0.0419(9) 0.0219(7) 0.0370(9) 0.0000(6) -0.0098(8) 0.0028(6) C15 0.0334(8) 0.0190(7) 0.0296(8) -0.0050(6) -0.0031(7) 0.0049(6) C16 0.0358(8) 0.0169(7) 0.0268(8) -0.0033(6) -0.0053(7) 0.0039(6) C17 0.0317(8) 0.0181(7) 0.0296(8) -0.0033(6) -0.0077(7) 0.0030(6) C18 0.0324(8) 0.0182(7) 0.0275(8) -0.0044(6) -0.0049(7) 0.0041(6) O19 0.0319(6) 0.0235(5) 0.0367(6) -0.0040(4) -0.0097(5) -0.0011(4) C20 0.0452(9) 0.0239(8) 0.0418(9) 0.0023(7) -0.0099(8) -0.0047(7) O21 0.0398(6) 0.0256(5) 0.0312(6) -0.0047(4) -0.0107(5) 0.0111(5) C22 0.0417(9) 0.0292(8) 0.0438(10) -0.0076(7) -0.0143(8) 0.0143(7) C23 0.0351(8) 0.0209(7) 0.0306(8) -0.0030(6) -0.0055(7) 0.0039(6) C24 0.0358(8) 0.0218(7) 0.0281(8) -0.0025(6) -0.0051(7) 0.0022(6) C25 0.0384(8) 0.0195(7) 0.0256(8) -0.0025(6) -0.0039(7) -0.0012(6) C26 0.0362(8) 0.0240(7) 0.0313(8) -0.0040(6) -0.0058(7) 0.0014(6) C27 0.0451(9) 0.0256(8) 0.0357(9) -0.0086(7) -0.0025(8) 0.0030(7) C28 0.0554(11) 0.0275(8) 0.0356(9) -0.0117(7) -0.0070(8) -0.0056(7) C29 0.0468(10) 0.0320(9) 0.0371(9) -0.0040(7) -0.0141(8) -0.0071(7) C30 0.0383(8) 0.0253(8) 0.0326(8) -0.0012(6) -0.0075(7) -0.0005(6) C31 0.0616(12) 0.0370(9) 0.0384(10) -0.0120(8) 0.0071(9) -0.0189(9) C32 0.0828(16) 0.0433(11) 0.0528(12) -0.0186(9) 0.0275(12) -0.0284(11) C33 0.0446(11) 0.0345(10) 0.0963(18) -0.0232(11) 0.0200(12) -0.0153(8) C34 0.0357(10) 0.0344(10) 0.1012(19) -0.0074(11) -0.0190(11) -0.0046(8) C35 0.0370(9) 0.0261(8) 0.0654(13) -0.0006(8) -0.0171(9) -0.0012(7) C36 0.0302(8) 0.0181(7) 0.0419(9) -0.0086(6) -0.0016(7) 0.0003(6) C37 0.0324(8) 0.0180(7) 0.0312(8) -0.0056(6) -0.0051(7) 0.0018(6) C38 0.0316(8) 0.0170(7) 0.0293(8) -0.0047(6) -0.0054(7) 0.0029(6) C39 0.0296(7) 0.0139(6) 0.0300(8) -0.0027(5) -0.0028(6) 0.0021(5) C40 0.0307(7) 0.0173(7) 0.0288(8) -0.0042(6) -0.0071(6) 0.0016(6) O41 0.0320(6) 0.0207(5) 0.0390(6) -0.0041(4) -0.0116(5) 0.0029(4) C42 0.0359(8) 0.0219(7) 0.0432(9) -0.0026(6) -0.0052(7) 0.0073(6) O43 0.0427(6) 0.0184(5) 0.0279(6) -0.0066(4) -0.0045(5) 0.0000(4) C44 0.0539(10) 0.0314(9) 0.0289(8) -0.0086(7) -0.0022(8) -0.0020(7) C45 0.0317(8) 0.0176(7) 0.0296(8) -0.0008(6) -0.0033(7) 0.0021(6) C46 0.0292(7) 0.0159(7) 0.0297(8) -0.0023(6) -0.0033(6) 0.0022(5) C47 0.0292(7) 0.0197(7) 0.0298(8) -0.0034(6) -0.0079(6) 0.0015(6) C48 0.0317(8) 0.0178(7) 0.0266(7) -0.0028(5) -0.0043(6) 0.0006(6) O49 0.0356(6) 0.0241(5) 0.0337(6) -0.0082(4) -0.0075(5) -0.0027(4) C50 0.0425(9) 0.0266(8) 0.0472(10) -0.0142(7) -0.0023(8) 0.0014(7) O51 0.0291(6) 0.0265(5) 0.0345(6) 0.0027(4) -0.0070(5) 0.0027(4) C52 0.0395(9) 0.0305(8) 0.0415(10) 0.0081(7) -0.0130(8) -0.0007(7) C53 0.0303(8) 0.0205(7) 0.0303(8) -0.0024(6) -0.0059(7) 0.0028(6) C54 0.0296(7) 0.0203(7) 0.0298(8) -0.0032(6) -0.0051(7) 0.0021(6) C55 0.0296(7) 0.0188(7) 0.0312(8) -0.0069(6) -0.0014(6) -0.0002(6) C56 0.0331(8) 0.0234(7) 0.0355(9) -0.0038(6) -0.0037(7) -0.0002(6) C57 0.0477(10) 0.0243(8) 0.0438(10) 0.0022(7) 0.0021(8) -0.0034(7) C58 0.0438(10) 0.0327(9) 0.0535(11) -0.0069(8) 0.0033(9) -0.0144(7) C59 0.0335(9) 0.0404(10) 0.0497(11) -0.0123(8) -0.0056(8) -0.0081(7) C60 0.0335(8) 0.0282(8) 0.0374(9) -0.0060(6) -0.0048(7) -0.0002(6) _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 1.379(2) . ? C1 C6 1.401(2) . ? C1 H1 0.9500 . ? C2 C3 1.381(3) . ? C2 H2 0.9500 . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? C5 C6 1.389(2) . ? C5 H5 0.9500 . ? C6 C7 1.433(2) . ? C7 C8 1.201(2) . ? C8 C9 1.428(2) . ? C9 C18 1.332(2) . ? C9 C10 1.520(2) . ? C10 O11 1.4127(18) . ? C10 O13 1.418(2) . ? C10 C15 1.500(2) . ? O11 C12 1.438(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? O13 C14 1.4330(19) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.332(2) . ? C15 H15 0.9500 . ? C16 C23 1.430(2) . ? C16 C17 1.519(2) . ? C17 O21 1.4014(19) . ? C17 O19 1.4217(18) . ? C17 C18 1.505(2) . ? C18 H18 0.9500 . ? O19 C20 1.425(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O21 C22 1.440(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C24 1.199(2) . ? C24 C25 1.433(2) . ? C25 C30 1.392(2) . ? C25 C26 1.404(2) . ? C26 C27 1.380(2) . ? C26 H26 0.9500 . ? C27 C28 1.386(3) . ? C27 H27 0.9500 . ? C28 C29 1.383(3) . ? C28 H28 0.9500 . ? C29 C30 1.387(2) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.392(3) . ? C31 C36 1.393(3) . ? C31 H31 0.9500 . ? C32 C33 1.377(4) . ? C32 H32 0.9500 . ? C33 C34 1.377(4) . ? C33 H33 0.9500 . ? C34 C35 1.382(3) . ? C34 H34 0.9500 . ? C35 C36 1.390(3) . ? C35 H35 0.9500 . ? C36 C37 1.436(2) . ? C37 C38 1.203(2) . ? C38 C39 1.432(2) . ? C39 C48 1.333(2) . ? C39 C40 1.522(2) . ? C40 O43 1.4090(17) . ? C40 O41 1.4189(19) . ? C40 C45 1.500(2) . ? O41 C42 1.4284(18) . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? O43 C44 1.432(2) . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 0.9800 . ? C45 C46 1.331(2) . ? C45 H45 0.9500 . ? C46 C53 1.431(2) . ? C46 C47 1.516(2) . ? C47 O51 1.4076(18) . ? C47 O49 1.4242(17) . ? C47 C48 1.504(2) . ? C48 H48 0.9500 . ? O49 C50 1.427(2) . ? C50 H50A 0.9800 . ? C50 H50B 0.9800 . ? C50 H50C 0.9800 . ? O51 C52 1.434(2) . ? C52 H52A 0.9800 . ? C52 H52B 0.9800 . ? C52 H52C 0.9800 . ? C53 C54 1.198(2) . ? C54 C55 1.433(2) . ? C55 C56 1.397(2) . ? C55 C60 1.396(2) . ? C56 C57 1.383(2) . ? C56 H56 0.9500 . ? C57 C58 1.388(3) . ? C57 H57 0.9500 . ? C58 C59 1.380(3) . ? C58 H58 0.9500 . ? C59 C60 1.388(2) . ? C59 H59 0.9500 . ? C60 H60 0.9500 . ? 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 C6 120.36(16) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C1 C2 C3 120.11(16) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 120.11(15) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 120.10(17) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.30(16) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 119.01(14) . . ? C5 C6 C7 120.91(14) . . ? C1 C6 C7 120.04(15) . . ? C8 C7 C6 177.02(16) . . ? C7 C8 C9 177.32(16) . . ? C18 C9 C8 121.05(14) . . ? C18 C9 C10 122.10(13) . . ? C8 C9 C10 116.85(13) . . ? O11 C10 O13 105.36(12) . . ? O11 C10 C15 112.47(12) . . ? O13 C10 C15 110.41(12) . . ? O11 C10 C9 104.93(11) . . ? O13 C10 C9 110.73(13) . . ? C15 C10 C9 112.60(13) . . ? C10 O11 C12 115.50(12) . . ? O11 C12 H12A 109.5 . . ? O11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 O13 C14 115.38(12) . . ? O13 C14 H14A 109.5 . . ? O13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C10 125.26(14) . . ? C16 C15 H15 117.4 . . ? C10 C15 H15 117.4 . . ? C15 C16 C23 121.94(14) . . ? C15 C16 C17 122.09(13) . . ? C23 C16 C17 115.95(14) . . ? O21 C17 O19 105.61(12) . . ? O21 C17 C18 112.14(12) . . ? O19 C17 C18 109.79(12) . . ? O21 C17 C16 105.46(12) . . ? O19 C17 C16 111.07(11) . . ? C18 C17 C16 112.50(13) . . ? C9 C18 C17 125.11(14) . . ? C9 C18 H18 117.4 . . ? C17 C18 H18 117.4 . . ? C17 O19 C20 115.10(12) . . ? O19 C20 H20A 109.5 . . ? O19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 O21 C22 115.33(13) . . ? O21 C22 H22A 109.5 . . ? O21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C24 C23 C16 176.19(17) . . ? C23 C24 C25 177.96(18) . . ? C30 C25 C26 119.04(14) . . ? C30 C25 C24 120.97(15) . . ? C26 C25 C24 119.98(15) . . ? C27 C26 C25 120.05(16) . . ? C27 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? C26 C27 C28 120.29(16) . . ? C26 C27 H27 119.9 . . ? C28 C27 H27 119.9 . . ? C29 C28 C27 120.22(15) . . ? C29 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? C28 C29 C30 119.85(17) . . ? C28 C29 H29 120.1 . . ? C30 C29 H29 120.1 . . ? C29 C30 C25 120.53(16) . . ? C29 C30 H30 119.7 . . ? C25 C30 H30 119.7 . . ? C32 C31 C36 119.9(2) . . ? C32 C31 H31 120.0 . . ? C36 C31 H31 120.0 . . ? C33 C32 C31 119.9(2) . . ? C33 C32 H32 120.0 . . ? C31 C32 H32 120.0 . . ? C32 C33 C34 120.51(18) . . ? C32 C33 H33 119.7 . . ? C34 C33 H33 119.7 . . ? C33 C34 C35 120.0(2) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C34 C35 C36 120.4(2) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C31 119.21(16) . . ? C35 C36 C37 119.99(16) . . ? C31 C36 C37 120.77(16) . . ? C38 C37 C36 178.51(16) . . ? C37 C38 C39 179.77(18) . . ? C48 C39 C38 121.97(14) . . ? C48 C39 C40 121.98(13) . . ? C38 C39 C40 116.05(13) . . ? O43 C40 O41 105.46(12) . . ? O43 C40 C45 112.61(12) . . ? O41 C40 C45 109.87(12) . . ? O43 C40 C39 105.13(11) . . ? O41 C40 C39 110.74(12) . . ? C45 C40 C39 112.72(13) . . ? C40 O41 C42 115.40(12) . . ? O41 C42 H42A 109.5 . . ? O41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? O41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C40 O43 C44 115.82(12) . . ? O43 C44 H44A 109.5 . . ? O43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? O43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C46 C45 C40 125.05(14) . . ? C46 C45 H45 117.5 . . ? C40 C45 H45 117.5 . . ? C45 C46 C53 121.54(14) . . ? C45 C46 C47 122.11(13) . . ? C53 C46 C47 116.35(13) . . ? O51 C47 O49 105.55(12) . . ? O51 C47 C48 112.53(12) . . ? O49 C47 C48 110.07(12) . . ? O51 C47 C46 104.74(12) . . ? O49 C47 C46 110.99(12) . . ? C48 C47 C46 112.64(13) . . ? C39 C48 C47 124.86(14) . . ? C39 C48 H48 117.6 . . ? C47 C48 H48 117.6 . . ? C47 O49 C50 114.48(12) . . ? O49 C50 H50A 109.5 . . ? O49 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? O49 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C47 O51 C52 115.68(12) . . ? O51 C52 H52A 109.5 . . ? O51 C52 H52B 109.5 . . ? H52A C52 H52B 109.5 . . ? O51 C52 H52C 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? C54 C53 C46 177.50(15) . . ? C53 C54 C55 178.56(16) . . ? C56 C55 C60 119.18(15) . . ? C56 C55 C54 120.45(14) . . ? C60 C55 C54 120.37(14) . . ? C57 C56 C55 120.08(16) . . ? C57 C56 H56 120.0 . . ? C55 C56 H56 120.0 . . ? C56 C57 C58 120.19(17) . . ? C56 C57 H57 119.9 . . ? C58 C57 H57 119.9 . . ? C59 C58 C57 120.29(16) . . ? C59 C58 H58 119.9 . . ? C57 C58 H58 119.9 . . ? C58 C59 C60 119.85(17) . . ? C58 C59 H59 120.1 . . ? C60 C59 H59 120.1 . . ? C59 C60 C55 120.40(16) . . ? C59 C60 H60 119.8 . . ? C55 C60 H60 119.8 . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 26.75 _diffrn_measured_fraction_theta_full 0.926 _refine_diff_density_max 0.234 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.049 data_compound3a _database_code_depnum_ccdc_archive 'CCDC 750181' #TrackingRef '- Compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 O4' _chemical_formula_sum 'C22 H20 O4' _chemical_formula_weight 348.38 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.222(2) _cell_length_b 7.6590(15) _cell_length_c 22.493(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.11(3) _cell_angle_gamma 90.00 _cell_volume 1721.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(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 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.75130 _diffrn_source synchrotron _diffrn_source_type 'ESRF-CRG BM16' _diffrn_radiation_monochromator 'Si 111' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9.6 _diffrn_radiation_detector 'ADSC Q210r CCD (binned mode)' _diffrn_measurement_device_type 'Single-axis HUBER diffractometer' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_number 2986 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0672 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.79 _reflns_number_total 2986 _reflns_number_gt 2926 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MxCube (ESRF, 2006)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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^)+(0.1279P)^2^+2.9689P] 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 2986 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0752 _refine_ls_R_factor_gt 0.0748 _refine_ls_wR_factor_ref 0.2537 _refine_ls_wR_factor_gt 0.2534 _refine_ls_goodness_of_fit_ref 1.152 _refine_ls_restrained_S_all 1.152 _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 O10 O 0.1128(2) 1.1944(3) 0.09204(9) 0.0142(5) Uani 1 1 d . . . O30 O 0.75019(19) 0.5280(3) 1.04875(9) 0.0123(5) Uani 1 1 d . . . O33 O 0.6466(2) 0.3040(3) 1.08565(9) 0.0123(5) Uani 1 1 d . . . O13 O 0.2528(2) 1.0248(3) 0.05088(9) 0.0143(5) Uani 1 1 d . . . C28 C 0.5797(3) 0.3735(4) 0.97961(12) 0.0104(6) Uani 1 1 d . . . H28 H 0.6335 0.2854 0.9671 0.012 Uiso 1 1 calc R . . C5 C -0.0371(3) 0.8017(4) 0.14984(14) 0.0152(7) Uani 1 1 d . . . H5 H -0.1254 0.8354 0.1307 0.018 Uiso 1 1 calc R . . C21 C 0.4296(3) 0.4370(4) 0.82533(13) 0.0150(7) Uani 1 1 d . . . H21 H 0.4448 0.5594 0.8274 0.018 Uiso 1 1 calc R . . C25 C 0.4120(3) 0.1620(4) 0.87454(13) 0.0137(7) Uani 1 1 d . . . H25 H 0.4158 0.0953 0.9105 0.016 Uiso 1 1 calc R . . C1 C 0.1971(3) 0.7843(4) 0.15006(15) 0.0198(7) Uani 1 1 d . . . H1 H 0.2705 0.8063 0.1313 0.024 Uiso 1 1 calc R . . C22 C 0.4019(3) 0.3542(4) 0.76911(13) 0.0173(7) Uani 1 1 d . . . H22 H 0.3995 0.4201 0.7331 0.021 Uiso 1 1 calc R . . C7 C 0.0365(3) 0.9117(4) 0.05863(13) 0.0115(6) Uani 1 1 d . . . C4 C -0.0148(3) 0.7217(4) 0.20647(14) 0.0190(7) Uani 1 1 d . . . H4 H -0.0875 0.7019 0.2259 0.023 Uiso 1 1 calc R . . C11 C 0.2312(3) 1.2971(4) 0.09601(14) 0.0177(7) Uani 1 1 d . . . H11A H 0.2646 1.3394 0.1380 0.021 Uiso 1 1 calc R . . H11B H 0.2141 1.3987 0.0683 0.021 Uiso 1 1 calc R . . C2 C 0.2189(3) 0.7038(5) 0.20662(15) 0.0252(8) Uani 1 1 d . . . H2 H 0.3071 0.6711 0.2262 0.030 Uiso 1 1 calc R . . C26 C 0.4355(3) 0.3421(4) 0.87865(12) 0.0107(6) Uani 1 1 d . . . C29 C 0.6236(3) 0.4436(4) 1.04303(12) 0.0096(6) Uani 1 1 d . . . C31 C 0.8526(3) 0.4015(4) 1.06917(16) 0.0221(8) Uani 1 1 d . . . H31A H 0.9183 0.4459 1.1047 0.027 Uiso 1 1 calc R . . H31B H 0.9001 0.3724 1.0364 0.027 Uiso 1 1 calc R . . C27 C 0.4717(3) 0.4247(4) 0.93971(12) 0.0099(6) Uani 1 1 d . . . C24 C 0.3830(3) 0.0803(4) 0.81817(14) 0.0172(7) Uani 1 1 d . . . H24 H 0.3667 -0.0419 0.8159 0.021 Uiso 1 1 calc R . . C32 C 0.7796(3) 0.2424(4) 1.08649(13) 0.0158(7) Uani 1 1 d . . . H32A H 0.7784 0.1468 1.0567 0.019 Uiso 1 1 calc R . . H32B H 0.8228 0.1997 1.1274 0.019 Uiso 1 1 calc R . . C6 C 0.0680(3) 0.8333(4) 0.12058(13) 0.0122(6) Uani 1 1 d . . . C12 C 0.3302(3) 1.1727(5) 0.07706(16) 0.0235(8) Uani 1 1 d . . . H12A H 0.3747 1.2284 0.0469 0.028 Uiso 1 1 calc R . . H12B H 0.3993 1.1368 0.1127 0.028 Uiso 1 1 calc R . . C9 C 0.1148(3) 1.0688(4) 0.04569(12) 0.0110(6) Uani 1 1 d . . . C23 C 0.3776(3) 0.1753(4) 0.76525(14) 0.0184(7) Uani 1 1 d . . . H23 H 0.3575 0.1189 0.7268 0.022 Uiso 1 1 calc R . . C8 C -0.0651(3) 0.8529(4) 0.01634(13) 0.0128(6) Uani 1 1 d . . . H8 H -0.1104 0.7522 0.0262 0.015 Uiso 1 1 calc R . . C3 C 0.1131(4) 0.6707(4) 0.23468(14) 0.0221(8) Uani 1 1 d . . . H3 H 0.1281 0.6134 0.2730 0.026 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 O10 0.0176(11) 0.0107(11) 0.0139(10) -0.0026(8) 0.0022(8) -0.0006(8) O30 0.0094(10) 0.0090(11) 0.0168(10) 0.0031(8) -0.0009(8) 0.0000(8) O33 0.0162(11) 0.0077(10) 0.0127(10) 0.0024(8) 0.0023(8) 0.0019(8) O13 0.0108(11) 0.0112(11) 0.0206(11) -0.0009(8) 0.0028(8) -0.0019(8) C28 0.0113(13) 0.0093(13) 0.0108(14) -0.0014(10) 0.0029(10) 0.0004(10) C5 0.0184(15) 0.0105(14) 0.0163(15) -0.0004(11) 0.0025(11) 0.0001(11) C21 0.0187(15) 0.0127(15) 0.0123(14) -0.0008(11) -0.0001(11) 0.0011(11) C25 0.0144(14) 0.0124(15) 0.0130(14) -0.0007(11) 0.0003(10) 0.0009(11) C1 0.0184(16) 0.0222(17) 0.0182(15) 0.0035(13) 0.0023(12) -0.0004(12) C22 0.0217(16) 0.0177(16) 0.0109(14) 0.0000(12) -0.0005(11) 0.0028(12) C7 0.0123(14) 0.0102(14) 0.0125(13) 0.0002(11) 0.0038(10) 0.0017(11) C4 0.0259(17) 0.0163(15) 0.0167(15) 0.0003(12) 0.0089(12) -0.0037(12) C11 0.0199(16) 0.0130(15) 0.0171(15) -0.0005(12) -0.0029(12) -0.0043(12) C2 0.0225(17) 0.0296(19) 0.0201(16) 0.0069(14) -0.0033(13) 0.0025(14) C26 0.0080(13) 0.0122(14) 0.0107(14) -0.0037(11) -0.0004(10) 0.0006(10) C29 0.0108(14) 0.0082(13) 0.0087(13) 0.0010(10) -0.0002(10) 0.0001(10) C31 0.0132(15) 0.0143(16) 0.0362(19) 0.0045(14) -0.0006(13) 0.0064(12) C27 0.0117(14) 0.0078(14) 0.0102(13) -0.0006(10) 0.0021(10) -0.0021(10) C24 0.0201(16) 0.0125(15) 0.0170(15) -0.0044(12) -0.0003(11) 0.0003(12) C32 0.0183(15) 0.0135(15) 0.0134(14) 0.0024(11) -0.0016(11) 0.0055(12) C6 0.0146(14) 0.0087(14) 0.0128(14) -0.0007(11) 0.0019(11) -0.0025(10) C12 0.0137(16) 0.0213(18) 0.0331(18) -0.0067(14) -0.0010(13) -0.0079(13) C9 0.0117(14) 0.0089(14) 0.0120(14) -0.0008(11) 0.0017(10) 0.0002(10) C23 0.0221(16) 0.0188(17) 0.0121(14) -0.0058(12) -0.0015(11) 0.0024(12) C8 0.0142(14) 0.0108(14) 0.0134(14) 0.0022(11) 0.0033(11) -0.0015(11) C3 0.0341(19) 0.0181(17) 0.0127(15) 0.0043(12) 0.0020(13) -0.0020(13) _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 O10 C9 1.422(3) . ? O10 C11 1.431(4) . ? O30 C31 1.429(4) . ? O30 C29 1.428(3) . ? O33 C29 1.423(3) . ? O33 C32 1.435(4) . ? O13 C9 1.432(3) . ? O13 C12 1.435(4) . ? C28 C27 1.327(4) . ? C28 C29 1.502(4) . ? C28 H28 0.9500 . ? C5 C4 1.389(4) . ? C5 C6 1.394(4) . ? C5 H5 0.9500 . ? C21 C22 1.390(4) . ? C21 C26 1.393(4) . ? C21 H21 0.9500 . ? C25 C24 1.389(4) . ? C25 C26 1.400(4) . ? C25 H25 0.9500 . ? C1 C2 1.389(5) . ? C1 C6 1.398(4) . ? C1 H1 0.9500 . ? C22 C23 1.392(5) . ? C22 H22 0.9500 . ? C7 C8 1.331(4) . ? C7 C6 1.489(4) . ? C7 C9 1.507(4) . ? C4 C3 1.384(5) . ? C4 H4 0.9500 . ? C11 C12 1.515(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C2 C3 1.386(5) . ? C2 H2 0.9500 . ? C26 C27 1.487(4) . ? C29 C27 1.508(4) 3_667 ? C31 C32 1.521(5) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C27 C29 1.508(4) 3_667 ? C24 C23 1.386(4) . ? C24 H24 0.9500 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C9 C8 1.505(4) 3_575 ? C23 H23 0.9500 . ? C8 C9 1.505(4) 3_575 ? C8 H8 0.9500 . ? C3 H3 0.9500 . ? 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 C9 O10 C11 106.0(2) . . ? C31 O30 C29 108.1(2) . . ? C29 O33 C32 106.2(2) . . ? C9 O13 C12 107.2(2) . . ? C27 C28 C29 125.2(3) . . ? C27 C28 H28 117.4 . . ? C29 C28 H28 117.4 . . ? C4 C5 C6 121.0(3) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C22 C21 C26 120.6(3) . . ? C22 C21 H21 119.7 . . ? C26 C21 H21 119.7 . . ? C24 C25 C26 120.3(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C2 C1 C6 120.5(3) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C21 C22 C23 120.4(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C8 C7 C6 121.0(3) . . ? C8 C7 C9 119.9(3) . . ? C6 C7 C9 118.9(2) . . ? C3 C4 C5 120.2(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? O10 C11 C12 104.0(2) . . ? O10 C11 H11A 110.9 . . ? C12 C11 H11A 110.9 . . ? O10 C11 H11B 110.9 . . ? C12 C11 H11B 110.9 . . ? H11A C11 H11B 109.0 . . ? C3 C2 C1 120.5(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C21 C26 C25 118.8(3) . . ? C21 C26 C27 122.0(3) . . ? C25 C26 C27 119.1(3) . . ? O33 C29 O30 105.1(2) . . ? O33 C29 C28 110.2(2) . . ? O30 C29 C28 109.4(2) . . ? O33 C29 C27 110.7(2) . 3_667 ? O30 C29 C27 107.3(2) . 3_667 ? C28 C29 C27 113.8(2) . 3_667 ? O30 C31 C32 105.1(2) . . ? O30 C31 H31A 110.7 . . ? C32 C31 H31A 110.7 . . ? O30 C31 H31B 110.7 . . ? C32 C31 H31B 110.7 . . ? H31A C31 H31B 108.8 . . ? C28 C27 C26 120.6(3) . . ? C28 C27 C29 120.9(3) . 3_667 ? C26 C27 C29 118.2(2) . 3_667 ? C23 C24 C25 120.7(3) . . ? C23 C24 H24 119.7 . . ? C25 C24 H24 119.7 . . ? O33 C32 C31 104.3(2) . . ? O33 C32 H32A 110.9 . . ? C31 C32 H32A 110.9 . . ? O33 C32 H32B 110.9 . . ? C31 C32 H32B 110.9 . . ? H32A C32 H32B 108.9 . . ? C5 C6 C1 118.3(3) . . ? C5 C6 C7 118.4(3) . . ? C1 C6 C7 123.3(3) . . ? O13 C12 C11 105.6(2) . . ? O13 C12 H12A 110.6 . . ? C11 C12 H12A 110.6 . . ? O13 C12 H12B 110.6 . . ? C11 C12 H12B 110.6 . . ? H12A C12 H12B 108.7 . . ? O10 C9 O13 105.4(2) . . ? O10 C9 C8 110.9(2) . 3_575 ? O13 C9 C8 107.7(2) . 3_575 ? O10 C9 C7 108.0(2) . . ? O13 C9 C7 110.5(2) . . ? C8 C9 C7 114.0(2) 3_575 . ? C24 C23 C22 119.2(3) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C7 C8 C9 126.1(3) . 3_575 ? C7 C8 H8 117.0 . . ? C9 C8 H8 117.0 3_575 . ? C4 C3 C2 119.5(3) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 26.79 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.453 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.080 data_compound5 _database_code_depnum_ccdc_archive 'CCDC 750182' #TrackingRef '- Compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 F6 O2 S2' _chemical_formula_weight 490.47 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9878(7) _cell_length_b 8.8208(9) _cell_length_c 10.2905(11) _cell_angle_alpha 93.730(5) _cell_angle_beta 109.110(6) _cell_angle_gamma 112.219(5) _cell_volume 541.74(10) _cell_formula_units_Z 1 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2559 _cell_measurement_theta_min 6.43 _cell_measurement_theta_max 65.46 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 250 _exptl_absorpt_coefficient_mu 2.866 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.5980 _exptl_absorpt_correction_T_max 0.6898 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator 'graded multilayer optics' _diffrn_measurement_device_type 'Bruker X8 Proteum' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6834 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 6.43 _diffrn_reflns_theta_max 65.96 _reflns_number_total 1771 _reflns_number_gt 1603 _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, 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. ; _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^)+(0.0983P)^2^+0.1689P] 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 1771 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1694 _refine_ls_wR_factor_gt 0.1647 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.4747(6) 0.5467(4) 0.8165(3) 0.0846(9) Uani 1 1 d . . . H1A H 0.5450 0.6607 0.8087 0.127 Uiso 1 1 calc R . . H1B H 0.5872 0.5110 0.8658 0.127 Uiso 1 1 calc R . . H1C H 0.3793 0.5390 0.8673 0.127 Uiso 1 1 calc R . . O2 O 0.3460(3) 0.4427(2) 0.68047(18) 0.0648(5) Uani 1 1 d . . . C3 C 0.1772(3) 0.4751(3) 0.5921(2) 0.0500(5) Uani 1 1 d . . . C4 C 0.0502(3) 0.3675(3) 0.4593(2) 0.0494(5) Uani 1 1 d . . . C5 C -0.1250(4) 0.3966(3) 0.3688(2) 0.0517(6) Uani 1 1 d . . . H5 H -0.2095 0.3276 0.2794 0.062 Uiso 1 1 calc R . . C6 C 0.0916(4) 0.2241(3) 0.4110(2) 0.0506(5) Uani 1 1 d . . . C7 C -0.0891(4) 0.0737(3) 0.3319(3) 0.0603(6) Uani 1 1 d . . . H7 H -0.2335 0.0633 0.3134 0.072 Uiso 1 1 calc R . . C8 C -0.0588(5) -0.0603(3) 0.2802(3) 0.0661(7) Uani 1 1 d . . . H8 H -0.1816 -0.1603 0.2284 0.079 Uiso 1 1 calc R . . C9 C 0.1564(5) -0.0446(3) 0.3064(3) 0.0633(7) Uani 1 1 d . . . S10 S 0.19815(17) -0.21746(10) 0.24204(9) 0.0885(4) Uani 1 1 d . . . C12 C 0.1928(5) -0.1778(4) 0.0757(3) 0.0830(9) Uani 1 1 d . . . F13 F 0.3420(5) -0.0262(4) 0.0805(3) 0.1333(10) Uani 1 1 d . . . F14 F 0.0043(4) -0.1824(4) -0.0096(2) 0.1319(9) Uani 1 1 d . . . F15 F 0.2336(7) -0.2885(5) 0.0125(3) 0.1692(14) Uani 1 1 d . . . C16 C 0.3375(4) 0.1022(3) 0.3869(3) 0.0653(7) Uani 1 1 d . . . H16 H 0.4816 0.1115 0.4064 0.078 Uiso 1 1 calc R . . C17 C 0.3064(4) 0.2355(3) 0.4386(3) 0.0595(6) Uani 1 1 d . . . H17 H 0.4300 0.3341 0.4925 0.071 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 C1 0.095(2) 0.087(2) 0.0610(16) 0.0043(14) 0.0014(14) 0.0541(17) O2 0.0677(10) 0.0636(10) 0.0604(10) 0.0051(8) 0.0104(7) 0.0383(8) C3 0.0515(11) 0.0497(12) 0.0518(12) 0.0117(9) 0.0189(9) 0.0249(9) C4 0.0541(11) 0.0467(11) 0.0539(12) 0.0108(9) 0.0260(9) 0.0235(9) C5 0.0562(12) 0.0498(12) 0.0485(12) 0.0067(9) 0.0184(9) 0.0236(10) C6 0.0595(12) 0.0486(12) 0.0536(12) 0.0140(9) 0.0276(10) 0.0274(10) C7 0.0611(13) 0.0534(13) 0.0704(15) 0.0080(11) 0.0282(11) 0.0265(11) C8 0.0771(15) 0.0506(13) 0.0736(16) 0.0078(11) 0.0335(13) 0.0269(12) C9 0.0893(17) 0.0582(14) 0.0640(14) 0.0190(11) 0.0389(13) 0.0443(13) S10 0.1397(8) 0.0777(6) 0.0873(6) 0.0237(4) 0.0542(5) 0.0758(6) C12 0.0874(19) 0.090(2) 0.0754(18) -0.0029(15) 0.0296(15) 0.0460(17) F13 0.1351(19) 0.139(2) 0.1217(19) 0.0276(15) 0.0774(16) 0.0304(16) F14 0.1221(18) 0.165(2) 0.0872(14) 0.0065(14) 0.0070(12) 0.0700(17) F15 0.287(4) 0.196(3) 0.119(2) 0.0237(19) 0.104(2) 0.178(3) C16 0.0711(15) 0.0714(16) 0.0735(16) 0.0193(13) 0.0352(12) 0.0437(13) C17 0.0591(13) 0.0550(13) 0.0711(15) 0.0121(11) 0.0297(11) 0.0273(11) _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 O2 1.412(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? O2 C3 1.373(3) . ? C3 C5 1.388(3) 2_566 ? C3 C4 1.399(3) . ? C4 C5 1.398(3) . ? C4 C6 1.489(3) . ? C5 C3 1.388(3) 2_566 ? C5 H5 0.9300 . ? C6 C7 1.392(3) . ? C6 C17 1.396(3) . ? C7 C8 1.381(3) . ? C7 H7 0.9300 . ? C8 C9 1.388(4) . ? C8 H8 0.9300 . ? C9 C16 1.378(4) . ? C9 S10 1.783(2) . ? S10 C12 1.761(4) . ? C12 F14 1.305(4) . ? C12 F15 1.307(4) . ? C12 F13 1.334(4) . ? C16 C17 1.378(3) . ? C16 H16 0.9300 . ? C17 H17 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 O2 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 O2 C1 118.4(2) . . ? O2 C3 C5 123.0(2) . 2_566 ? O2 C3 C4 116.88(19) . . ? C5 C3 C4 120.07(19) 2_566 . ? C5 C4 C3 117.7(2) . . ? C5 C4 C6 119.00(19) . . ? C3 C4 C6 123.29(19) . . ? C3 C5 C4 122.2(2) 2_566 . ? C3 C5 H5 118.9 2_566 . ? C4 C5 H5 118.9 . . ? C7 C6 C17 118.0(2) . . ? C7 C6 C4 119.48(19) . . ? C17 C6 C4 122.5(2) . . ? C8 C7 C6 121.5(2) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C7 C8 C9 119.4(2) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C16 C9 C8 119.9(2) . . ? C16 C9 S10 120.2(2) . . ? C8 C9 S10 119.9(2) . . ? C12 S10 C9 99.72(13) . . ? F14 C12 F15 107.1(3) . . ? F14 C12 F13 103.0(3) . . ? F15 C12 F13 107.5(3) . . ? F14 C12 S10 115.2(2) . . ? F15 C12 S10 109.5(3) . . ? F13 C12 S10 114.0(2) . . ? C9 C16 C17 120.5(2) . . ? C9 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C16 C17 C6 120.7(2) . . ? C16 C17 H17 119.6 . . ? C6 C17 H17 119.6 . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 65.96 _diffrn_measured_fraction_theta_full 0.935 _refine_diff_density_max 0.329 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.044 data_compound5a _database_code_depnum_ccdc_archive 'CCDC 750183' #TrackingRef '- Compounds.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H22 F6 O4 S2' _chemical_formula_weight 552.54 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.639(3) _cell_length_b 6.3760(13) _cell_length_c 27.642(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.69(3) _cell_angle_gamma 90.00 _cell_volume 2395.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(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 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.75130 _diffrn_source synchrotron _diffrn_source_type 'ESRF-CRG BM16' _diffrn_radiation_monochromator 'Si 111' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9.6 _diffrn_radiation_detector 'ADSC Q210r CCD (binned mode)' _diffrn_measurement_device_type 'Single-axis HUBER diffractometer' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_number 3963 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 26.75 _reflns_number_total 3963 _reflns_number_gt 3921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MxCube (ESRF, 2006)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _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^)+(0.0911P)^2^+2.1348P] 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 3963 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1474 _refine_ls_wR_factor_gt 0.1473 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 S1 S 0.58081(4) 0.68912(8) 0.231993(16) 0.01750(19) Uani 1 1 d . . . S2 S -0.05938(4) 0.34589(8) -0.231621(17) 0.0189(2) Uani 1 1 d . . . F3 F 0.69790(12) 0.8951(2) 0.17772(6) 0.0421(4) Uani 1 1 d . . . F1 F 0.76597(10) 0.7536(2) 0.24239(5) 0.0327(4) Uani 1 1 d . . . F2 F 0.72260(9) 0.5654(2) 0.17969(5) 0.0315(3) Uani 1 1 d . . . F6 F -0.22340(13) 0.1706(3) -0.25314(7) 0.0535(6) Uani 1 1 d . . . O2 O 0.24515(10) 0.81567(18) -0.06261(5) 0.0108(3) Uani 1 1 d . . . C8 C 0.06277(15) 0.2113(3) -0.15265(7) 0.0147(4) Uani 1 1 d . . . H8 H 0.0625 0.0776 -0.1678 0.018 Uiso 1 1 calc R . . O3 O 0.26182(10) 0.19454(18) 0.06850(5) 0.0113(3) Uani 1 1 d . . . O4 O 0.37797(10) 0.19901(19) 0.01937(5) 0.0111(3) Uani 1 1 d . . . C11 C 0.18441(13) 0.4710(3) -0.04022(6) 0.0088(4) Uani 1 1 d . . . C12 C 0.06612(13) 0.6039(3) -0.10883(7) 0.0121(4) Uani 1 1 d . . . H12 H 0.0678 0.7392 -0.0944 0.015 Uiso 1 1 calc R . . F5 F -0.12946(14) -0.0058(3) -0.20158(8) 0.0673(7) Uani 1 1 d . . . C14 C 0.00963(13) 0.5711(3) -0.15221(7) 0.0134(4) Uani 1 1 d . . . H14 H -0.0279 0.6831 -0.1669 0.016 Uiso 1 1 calc R . . F4 F -0.20472(14) 0.2674(4) -0.17959(7) 0.0749(7) Uani 1 1 d . . . C16 C 0.00768(14) 0.3750(3) -0.17421(6) 0.0125(4) Uani 1 1 d . . . C17 C 0.45105(15) 0.8062(3) 0.15542(7) 0.0171(4) Uani 1 1 d . . . H17 H 0.4543 0.9423 0.1694 0.021 Uiso 1 1 calc R . . C18 C 0.32120(13) 0.5395(3) 0.04596(6) 0.0088(4) Uani 1 1 d . . . C19 C 0.21256(14) 0.6935(3) -0.02425(6) 0.0093(4) Uani 1 1 d . . . C20 C 0.28668(13) 0.7016(3) 0.01913(6) 0.0100(4) Uani 1 1 d . . . H20 H 0.3115 0.8361 0.0284 0.012 Uiso 1 1 calc R . . C21 C 0.38626(13) 0.5714(3) 0.09134(6) 0.0098(4) Uani 1 1 d . . . C22 C 0.50042(14) 0.4439(3) 0.15686(7) 0.0135(4) Uani 1 1 d . . . H22 H 0.5370 0.3317 0.1721 0.016 Uiso 1 1 calc R . . C23 C 0.44125(14) 0.4085(3) 0.11433(7) 0.0117(4) Uani 1 1 d . . . H23 H 0.4380 0.2718 0.1006 0.014 Uiso 1 1 calc R . . C24 C 0.12074(13) 0.4403(3) -0.08599(6) 0.0095(4) Uani 1 1 d . . . C25 C 0.29312(14) 0.3175(3) 0.02997(7) 0.0092(4) Uani 1 1 d . . . C26 C 0.21835(14) 0.3091(3) -0.01320(7) 0.0102(4) Uani 1 1 d . . . H26 H 0.1927 0.1747 -0.0221 0.012 Uiso 1 1 calc R . . C27 C 0.33203(14) 0.7418(3) -0.08199(7) 0.0152(4) Uani 1 1 d . . . H27A H 0.3866 0.7444 -0.0567 0.023 Uiso 1 1 calc R . . H27B H 0.3478 0.8321 -0.1090 0.023 Uiso 1 1 calc R . . H27C H 0.3217 0.5978 -0.0937 0.023 Uiso 1 1 calc R . . C28 C 0.50617(14) 0.6439(3) 0.17722(7) 0.0136(4) Uani 1 1 d . . . O1 O 0.12795(10) 0.81304(18) -0.01412(5) 0.0115(3) Uani 1 1 d . . . C30 C 0.39136(14) 0.7703(3) 0.11334(7) 0.0142(4) Uani 1 1 d . . . H30 H 0.3531 0.8821 0.0991 0.017 Uiso 1 1 calc R . . C36 C 0.42128(14) 0.2524(3) -0.02408(7) 0.0156(4) Uani 1 1 d . . . H36A H 0.3736 0.2286 -0.0520 0.023 Uiso 1 1 calc R . . H36B H 0.4795 0.1649 -0.0272 0.023 Uiso 1 1 calc R . . H36C H 0.4406 0.4004 -0.0230 0.023 Uiso 1 1 calc R . . C32 C 0.69618(17) 0.7274(3) 0.20646(8) 0.0230(5) Uani 1 1 d . . . C33 C 0.11807(14) 0.2436(3) -0.10902(7) 0.0125(4) Uani 1 1 d . . . H33 H 0.1549 0.1307 -0.0944 0.015 Uiso 1 1 calc R . . C34 C -0.1586(2) 0.1902(4) -0.21496(10) 0.0362(6) Uani 1 1 d . . . C35 C 0.07982(15) 0.7523(3) 0.02745(7) 0.0182(4) Uani 1 1 d . . . H35A H 0.0578 0.6064 0.0238 0.027 Uiso 1 1 calc R . . H35B H 0.0228 0.8434 0.0306 0.027 Uiso 1 1 calc R . . H35C H 0.1256 0.7654 0.0565 0.027 Uiso 1 1 calc R . . C37 C 0.17640(16) 0.2696(3) 0.08911(8) 0.0195(4) Uani 1 1 d . . . H37A H 0.1894 0.4095 0.1029 0.029 Uiso 1 1 calc R . . H37B H 0.1592 0.1738 0.1148 0.029 Uiso 1 1 calc R . . H37C H 0.1217 0.2773 0.0639 0.029 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 S1 0.0210(3) 0.0191(3) 0.0115(3) -0.00231(17) -0.00389(19) 0.00163(18) S2 0.0219(3) 0.0207(3) 0.0131(3) 0.00007(18) -0.00551(19) -0.00061(19) F3 0.0439(9) 0.0341(8) 0.0475(9) 0.0209(7) -0.0011(7) -0.0115(7) F1 0.0262(7) 0.0354(8) 0.0342(8) -0.0043(6) -0.0124(6) -0.0099(6) F2 0.0252(7) 0.0370(8) 0.0327(7) -0.0105(6) 0.0054(5) -0.0048(6) F6 0.0468(10) 0.0422(9) 0.0640(11) 0.0194(8) -0.0419(9) -0.0236(7) O2 0.0153(7) 0.0031(6) 0.0138(7) 0.0031(4) 0.0004(5) 0.0005(5) C8 0.0186(10) 0.0080(8) 0.0172(9) -0.0031(7) -0.0011(7) -0.0007(7) O3 0.0157(7) 0.0036(6) 0.0147(7) 0.0039(5) 0.0014(5) 0.0009(5) O4 0.0161(7) 0.0038(6) 0.0132(6) 0.0007(4) 0.0009(5) 0.0043(5) C11 0.0104(9) 0.0029(8) 0.0131(8) -0.0014(6) 0.0007(6) -0.0004(6) C12 0.0145(9) 0.0051(8) 0.0166(9) -0.0004(7) 0.0004(7) 0.0005(7) F5 0.0656(12) 0.0350(9) 0.0931(14) 0.0371(10) -0.0435(10) -0.0255(8) C14 0.0139(9) 0.0098(9) 0.0161(9) 0.0027(7) -0.0009(7) 0.0024(7) F4 0.0317(10) 0.135(2) 0.0597(12) -0.0070(13) 0.0154(8) -0.0293(11) C16 0.0124(9) 0.0127(9) 0.0119(9) 0.0001(7) -0.0014(7) -0.0009(7) C17 0.0255(11) 0.0078(9) 0.0175(10) -0.0041(7) -0.0015(8) 0.0007(7) C18 0.0106(9) 0.0033(8) 0.0125(8) -0.0017(6) 0.0009(6) -0.0004(6) C19 0.0136(9) 0.0020(8) 0.0123(9) 0.0010(6) 0.0001(7) 0.0015(6) C20 0.0138(9) 0.0027(8) 0.0132(9) -0.0010(6) 0.0001(7) -0.0012(6) C21 0.0121(9) 0.0046(8) 0.0126(8) 0.0009(7) 0.0014(6) -0.0012(6) C22 0.0157(9) 0.0092(9) 0.0151(9) 0.0019(7) -0.0007(7) 0.0029(7) C23 0.0146(9) 0.0059(8) 0.0142(9) 0.0001(7) 0.0001(7) 0.0005(7) C24 0.0102(9) 0.0058(8) 0.0125(8) 0.0010(7) 0.0007(6) -0.0010(6) C25 0.0137(9) 0.0016(8) 0.0122(9) 0.0012(6) 0.0000(7) 0.0014(6) C26 0.0138(9) 0.0026(8) 0.0139(9) -0.0006(6) -0.0009(7) -0.0012(6) C27 0.0179(10) 0.0092(8) 0.0191(9) 0.0030(7) 0.0050(7) 0.0009(7) C28 0.0160(10) 0.0136(9) 0.0110(9) -0.0004(7) -0.0005(7) -0.0001(7) O1 0.0163(7) 0.0038(6) 0.0143(7) 0.0013(5) 0.0017(5) 0.0040(5) C30 0.0202(10) 0.0069(8) 0.0147(9) -0.0004(7) -0.0031(7) 0.0036(7) C36 0.0179(10) 0.0113(9) 0.0179(9) 0.0025(7) 0.0041(7) 0.0032(7) C32 0.0260(11) 0.0191(10) 0.0224(11) 0.0025(8) -0.0064(8) -0.0077(8) C33 0.0162(9) 0.0045(8) 0.0164(9) 0.0005(7) -0.0020(7) 0.0022(7) C34 0.0323(14) 0.0351(13) 0.0382(14) 0.0156(11) -0.0156(11) -0.0173(11) C35 0.0193(10) 0.0136(9) 0.0227(10) 0.0039(8) 0.0069(8) 0.0046(8) C37 0.0219(11) 0.0121(9) 0.0261(10) 0.0052(8) 0.0107(8) 0.0017(8) _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 S1 C28 1.7777(19) . ? S1 C32 1.793(2) . ? S2 C34 1.770(2) . ? S2 C16 1.7754(19) . ? F3 C32 1.334(3) . ? F1 C32 1.329(2) . ? F2 C32 1.337(3) . ? F6 C34 1.326(3) . ? O2 C19 1.416(2) . ? O2 C27 1.420(2) . ? C8 C33 1.385(3) . ? C8 C16 1.391(3) . ? C8 H8 0.9500 . ? O3 C25 1.416(2) . ? O3 C37 1.421(2) . ? O4 C36 1.422(2) . ? O4 C25 1.432(2) . ? C11 C26 1.335(3) . ? C11 C24 1.488(2) . ? C11 C19 1.525(2) . ? C12 C14 1.387(3) . ? C12 C24 1.402(2) . ? C12 H12 0.9500 . ? F5 C34 1.354(3) . ? C14 C16 1.390(3) . ? C14 H14 0.9500 . ? F4 C34 1.301(4) . ? C17 C30 1.383(3) . ? C17 C28 1.387(3) . ? C17 H17 0.9500 . ? C18 C20 1.335(3) . ? C18 C21 1.490(2) . ? C18 C25 1.523(2) . ? C19 O1 1.430(2) . ? C19 C20 1.505(2) . ? C20 H20 0.9500 . ? C21 C23 1.403(2) . ? C21 C30 1.405(3) . ? C22 C23 1.389(3) . ? C22 C28 1.393(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C33 1.405(2) . ? C25 C26 1.506(3) . ? C26 H26 0.9500 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? O1 C35 1.423(2) . ? C30 H30 0.9500 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C33 H33 0.9500 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? 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 C28 S1 C32 98.44(9) . . ? C34 S2 C16 100.08(10) . . ? C19 O2 C27 114.99(13) . . ? C33 C8 C16 119.87(17) . . ? C33 C8 H8 120.1 . . ? C16 C8 H8 120.1 . . ? C25 O3 C37 115.00(13) . . ? C36 O4 C25 116.42(13) . . ? C26 C11 C24 121.70(16) . . ? C26 C11 C19 119.33(16) . . ? C24 C11 C19 118.97(15) . . ? C14 C12 C24 120.95(16) . . ? C14 C12 H12 119.5 . . ? C24 C12 H12 119.5 . . ? C12 C14 C16 120.22(16) . . ? C12 C14 H14 119.9 . . ? C16 C14 H14 119.9 . . ? C14 C16 C8 119.81(16) . . ? C14 C16 S2 118.37(14) . . ? C8 C16 S2 121.69(14) . . ? C30 C17 C28 120.17(17) . . ? C30 C17 H17 119.9 . . ? C28 C17 H17 119.9 . . ? C20 C18 C21 121.36(16) . . ? C20 C18 C25 119.31(16) . . ? C21 C18 C25 119.32(14) . . ? O2 C19 O1 99.26(13) . . ? O2 C19 C20 110.26(14) . . ? O1 C19 C20 109.03(14) . . ? O2 C19 C11 112.44(14) . . ? O1 C19 C11 111.37(15) . . ? C20 C19 C11 113.54(14) . . ? C18 C20 C19 126.83(16) . . ? C18 C20 H20 116.6 . . ? C19 C20 H20 116.6 . . ? C23 C21 C30 117.81(16) . . ? C23 C21 C18 122.65(16) . . ? C30 C21 C18 119.51(15) . . ? C23 C22 C28 120.01(17) . . ? C23 C22 H22 120.0 . . ? C28 C22 H22 120.0 . . ? C22 C23 C21 121.00(16) . . ? C22 C23 H23 119.5 . . ? C21 C23 H23 119.5 . . ? C12 C24 C33 117.83(16) . . ? C12 C24 C11 122.46(16) . . ? C33 C24 C11 119.63(15) . . ? O3 C25 O4 99.23(13) . . ? O3 C25 C26 110.49(14) . . ? O4 C25 C26 108.99(14) . . ? O3 C25 C18 112.36(14) . . ? O4 C25 C18 111.19(15) . . ? C26 C25 C18 113.64(14) . . ? C11 C26 C25 126.68(16) . . ? C11 C26 H26 116.7 . . ? C25 C26 H26 116.7 . . ? O2 C27 H27A 109.5 . . ? O2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C17 C28 C22 119.77(17) . . ? C17 C28 S1 120.08(15) . . ? C22 C28 S1 120.12(14) . . ? C35 O1 C19 116.50(14) . . ? C17 C30 C21 121.20(17) . . ? C17 C30 H30 119.4 . . ? C21 C30 H30 119.4 . . ? O4 C36 H36A 109.5 . . ? O4 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O4 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? F1 C32 F3 107.33(17) . . ? F1 C32 F2 107.57(18) . . ? F3 C32 F2 105.73(18) . . ? F1 C32 S1 108.72(15) . . ? F3 C32 S1 113.71(16) . . ? F2 C32 S1 113.43(14) . . ? C8 C33 C24 121.30(17) . . ? C8 C33 H33 119.3 . . ? C24 C33 H33 119.3 . . ? F4 C34 F6 107.6(2) . . ? F4 C34 F5 107.1(2) . . ? F6 C34 F5 107.0(2) . . ? F4 C34 S2 114.2(2) . . ? F6 C34 S2 108.64(17) . . ? F5 C34 S2 112.0(2) . . ? O1 C35 H35A 109.5 . . ? O1 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O1 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? O3 C37 H37A 109.5 . . ? O3 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O3 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 26.75 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.960 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.063