# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Bao-Sheng Li' _publ_contact_author_email libaoshengqq@163.com loop_ _publ_author_name 'Bao-Sheng Li' 'Bin-Miao Yang' 'Shao-Hua Wang' 'Yong-Qiang Zhang' 'Xiaoping Cao' 'Yong Qiang Tu' data_p21c _database_code_depnum_ccdc_archive 'CCDC 855318' #TrackingRef '- product 1d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H12 O3' _chemical_formula_weight 204.22 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.846(3) _cell_length_b 6.8888(16) _cell_length_c 12.417(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.999(2) _cell_angle_gamma 90.00 _cell_volume 997.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3234 _cell_measurement_theta_min 3.33 _cell_measurement_theta_max 27.80 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9779 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 6968 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1857 _reflns_number_gt 1567 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+0.1799P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.185(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1857 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1373 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 0.13658(15) 0.5077(2) 0.41745(14) 0.0495(4) Uani 1 1 d . . . H1A H 0.1318 0.6070 0.4719 0.059 Uiso 1 1 calc R . . H1B H 0.1661 0.5678 0.3574 0.059 Uiso 1 1 calc R . . C2 C 0.21926(14) 0.3489(2) 0.46791(13) 0.0418(4) Uani 1 1 d . . . H2 H 0.2887 0.3899 0.5175 0.050 Uiso 1 1 calc R . . C3 C 0.23370(12) 0.2037(2) 0.37787(12) 0.0370(4) Uani 1 1 d . . . H3 H 0.2358 0.2612 0.3060 0.044 Uiso 1 1 calc R . . C4 C 0.11720(12) 0.1162(2) 0.39182(12) 0.0370(4) Uani 1 1 d . . . H4 H 0.1076 -0.0244 0.3820 0.044 Uiso 1 1 calc R . . C5 C 0.02248(13) 0.2462(2) 0.33089(13) 0.0443(4) Uani 1 1 d . . . H5A H 0.0319 0.2580 0.2551 0.053 Uiso 1 1 calc R . . H5B H -0.0515 0.1868 0.3323 0.053 Uiso 1 1 calc R . . C6 C 0.14640(13) 0.1918(2) 0.50852(12) 0.0418(4) Uani 1 1 d . . . C7 C 0.34270(12) -0.0806(2) 0.35499(12) 0.0396(4) Uani 1 1 d . . . C8 C 0.28753(14) -0.1074(2) 0.24838(13) 0.0456(4) Uani 1 1 d . . . H8 H 0.2342 -0.0172 0.2151 0.055 Uiso 1 1 calc R . . C9 C 0.31285(16) -0.2702(3) 0.19201(15) 0.0560(5) Uani 1 1 d . . . H9 H 0.2764 -0.2889 0.1202 0.067 Uiso 1 1 calc R . . C10 C 0.39130(17) -0.4051(3) 0.24080(19) 0.0641(6) Uani 1 1 d . . . H10 H 0.4079 -0.5139 0.2021 0.077 Uiso 1 1 calc R . . C11 C 0.44482(16) -0.3778(3) 0.34722(19) 0.0622(5) Uani 1 1 d . . . H11 H 0.4975 -0.4690 0.3805 0.075 Uiso 1 1 calc R . . C12 C 0.42105(14) -0.2164(3) 0.40502(15) 0.0503(5) Uani 1 1 d . . . H12 H 0.4573 -0.1988 0.4770 0.060 Uiso 1 1 calc R . . O1 O 0.02500(11) 0.43291(17) 0.37836(10) 0.0559(4) Uani 1 1 d . . . O2 O 0.12905(13) 0.1401(2) 0.59589(10) 0.0655(4) Uani 1 1 d . . . O3 O 0.32693(9) 0.07822(17) 0.41814(9) 0.0464(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0596(10) 0.0343(8) 0.0565(10) -0.0009(7) 0.0152(8) -0.0003(7) C2 0.0448(9) 0.0395(8) 0.0403(8) -0.0060(6) 0.0050(6) -0.0052(6) C3 0.0368(8) 0.0375(8) 0.0367(7) 0.0009(6) 0.0065(6) 0.0009(6) C4 0.0388(8) 0.0314(7) 0.0410(8) 0.0005(6) 0.0074(6) -0.0010(6) C5 0.0404(8) 0.0460(9) 0.0454(9) 0.0002(7) 0.0045(7) 0.0030(7) C6 0.0469(9) 0.0413(8) 0.0383(8) 0.0047(6) 0.0104(7) 0.0067(6) C7 0.0312(7) 0.0412(8) 0.0481(9) -0.0014(6) 0.0116(6) -0.0012(6) C8 0.0431(9) 0.0487(9) 0.0465(9) 0.0001(7) 0.0118(7) 0.0033(7) C9 0.0572(10) 0.0588(11) 0.0554(10) -0.0112(8) 0.0195(8) -0.0020(9) C10 0.0588(11) 0.0502(10) 0.0897(15) -0.0154(10) 0.0308(11) 0.0009(8) C11 0.0458(10) 0.0483(10) 0.0941(16) 0.0054(10) 0.0169(9) 0.0097(8) C12 0.0366(8) 0.0515(10) 0.0620(11) 0.0053(8) 0.0066(7) 0.0032(7) O1 0.0550(7) 0.0453(7) 0.0648(8) -0.0018(5) 0.0032(6) 0.0119(5) O2 0.0862(10) 0.0733(9) 0.0411(7) 0.0158(6) 0.0228(6) 0.0076(7) O3 0.0392(6) 0.0505(7) 0.0466(6) -0.0072(5) -0.0010(5) 0.0071(5) _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 O1 1.423(2) . ? C1 C2 1.529(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C6 1.524(2) . ? C2 C3 1.531(2) . ? C2 H2 0.9800 . ? C3 O3 1.4233(18) . ? C3 C4 1.543(2) . ? C3 H3 0.9800 . ? C4 C6 1.522(2) . ? C4 C5 1.529(2) . ? C4 H4 0.9800 . ? C5 O1 1.413(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 O2 1.1930(19) . ? C7 O3 1.3777(19) . ? C7 C8 1.383(2) . ? C7 C12 1.386(2) . ? C8 C9 1.382(2) . ? C8 H8 0.9300 . ? C9 C10 1.378(3) . ? C9 H9 0.9300 . ? C10 C11 1.376(3) . ? C10 H10 0.9300 . ? C11 C12 1.379(3) . ? C11 H11 0.9300 . ? C12 H12 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 O1 C1 C2 111.81(13) . . ? O1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? O1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C6 C2 C1 106.54(13) . . ? C6 C2 C3 85.37(11) . . ? C1 C2 C3 108.24(13) . . ? C6 C2 H2 117.3 . . ? C1 C2 H2 117.3 . . ? C3 C2 H2 117.3 . . ? O3 C3 C2 108.56(12) . . ? O3 C3 C4 112.19(12) . . ? C2 C3 C4 87.58(11) . . ? O3 C3 H3 115.1 . . ? C2 C3 H3 115.1 . . ? C4 C3 H3 115.1 . . ? C6 C4 C5 107.25(12) . . ? C6 C4 C3 85.03(11) . . ? C5 C4 C3 108.00(12) . . ? C6 C4 H4 117.3 . . ? C5 C4 H4 117.3 . . ? C3 C4 H4 117.3 . . ? O1 C5 C4 111.48(12) . . ? O1 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? O1 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? O2 C6 C4 135.82(16) . . ? O2 C6 C2 135.22(16) . . ? C4 C6 C2 88.63(11) . . ? O3 C7 C8 124.22(14) . . ? O3 C7 C12 115.29(14) . . ? C8 C7 C12 120.48(15) . . ? C9 C8 C7 119.00(16) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? C10 C9 C8 120.91(18) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C11 C10 C9 119.54(17) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C10 C11 C12 120.58(17) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 119.48(17) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? C5 O1 C1 115.03(12) . . ? C7 O3 C3 117.14(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C6 -26.56(17) . . . . ? O1 C1 C2 C3 63.97(17) . . . . ? C6 C2 C3 O3 -85.60(13) . . . . ? C1 C2 C3 O3 168.49(12) . . . . ? C6 C2 C3 C4 27.01(11) . . . . ? C1 C2 C3 C4 -78.89(13) . . . . ? O3 C3 C4 C6 82.01(12) . . . . ? C2 C3 C4 C6 -27.06(11) . . . . ? O3 C3 C4 C5 -171.45(11) . . . . ? C2 C3 C4 C5 79.48(13) . . . . ? C6 C4 C5 O1 25.50(17) . . . . ? C3 C4 C5 O1 -64.81(16) . . . . ? C5 C4 C6 O2 106.1(2) . . . . ? C3 C4 C6 O2 -146.6(2) . . . . ? C5 C4 C6 C2 -80.13(13) . . . . ? C3 C4 C6 C2 27.19(11) . . . . ? C1 C2 C6 O2 -105.9(2) . . . . ? C3 C2 C6 O2 146.4(2) . . . . ? C1 C2 C6 C4 80.27(13) . . . . ? C3 C2 C6 C4 -27.40(11) . . . . ? O3 C7 C8 C9 178.11(14) . . . . ? C12 C7 C8 C9 -0.9(2) . . . . ? C7 C8 C9 C10 0.4(3) . . . . ? C8 C9 C10 C11 0.3(3) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C10 C11 C12 C7 -0.2(3) . . . . ? O3 C7 C12 C11 -178.27(14) . . . . ? C8 C7 C12 C11 0.8(2) . . . . ? C4 C5 O1 C1 37.43(18) . . . . ? C2 C1 O1 C5 -36.96(18) . . . . ? C8 C7 O3 C3 11.6(2) . . . . ? C12 C7 O3 C3 -169.34(12) . . . . ? C2 C3 O3 C7 170.58(12) . . . . ? C4 C3 O3 C7 75.48(16) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.333 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.033 # Attachment '- product 4d.cif' data_p-1 _database_code_depnum_ccdc_archive 'CCDC 855319' #TrackingRef '- product 4d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 O3' _chemical_formula_weight 218.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 9.013(16) _cell_length_b 9.018(15) _cell_length_c 28.90(5) _cell_angle_alpha 87.731(19) _cell_angle_beta 87.947(19) _cell_angle_gamma 89.841(19) _cell_volume 2346(7) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2419 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 20.56 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9819 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15033 _diffrn_reflns_av_R_equivalents 0.0546 _diffrn_reflns_av_sigmaI/netI 0.1002 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 25.20 _reflns_number_total 8240 _reflns_number_gt 4048 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1754P)^2^+9.9803P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8240 _refine_ls_number_parameters 578 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2098 _refine_ls_R_factor_gt 0.1342 _refine_ls_wR_factor_ref 0.4396 _refine_ls_wR_factor_gt 0.3925 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 0.4852(9) 0.3652(9) 0.0737(3) 0.054(2) Uani 1 1 d . . . C2 C 0.6112(9) 0.3373(9) 0.0373(3) 0.057(2) Uani 1 1 d . . . H2 H 0.6706 0.4231 0.0261 0.068 Uiso 1 1 calc R . . C3 C 0.5470(9) 0.2389(10) 0.0005(3) 0.062(2) Uani 1 1 d . . . H3A H 0.5186 0.3005 -0.0260 0.075 Uiso 1 1 calc R . . H3B H 0.6223 0.1695 -0.0100 0.075 Uiso 1 1 calc R . . C4 C 0.4416(11) 0.0973(11) 0.0643(3) 0.077(3) Uani 1 1 d . . . H4A H 0.5048 0.0103 0.0625 0.093 Uiso 1 1 calc R . . H4B H 0.3464 0.0665 0.0782 0.093 Uiso 1 1 calc R . . C5 C 0.5143(9) 0.2136(9) 0.0954(3) 0.059(2) Uani 1 1 d . . . H5 H 0.4996 0.2004 0.1290 0.070 Uiso 1 1 calc R . . C6 C 0.6763(8) 0.2364(9) 0.0755(3) 0.057(2) Uani 1 1 d . . . H6 H 0.7243 0.1462 0.0644 0.068 Uiso 1 1 calc R . . C7 C 0.8303(14) 0.2376(11) 0.1402(4) 0.092(4) Uani 1 1 d . . . H7A H 0.8911 0.1588 0.1276 0.111 Uiso 1 1 calc R . . H7B H 0.7522 0.1929 0.1601 0.111 Uiso 1 1 calc R . . C8 C 0.9239(10) 0.3381(9) 0.1676(3) 0.060(2) Uani 1 1 d . . . C9 C 0.8609(10) 0.4228(11) 0.2023(4) 0.073(3) Uani 1 1 d . . . H9 H 0.7593 0.4161 0.2087 0.088 Uiso 1 1 calc R . . C10 C 0.9424(16) 0.5143(12) 0.2269(4) 0.089(3) Uani 1 1 d . . . H10 H 0.8962 0.5673 0.2504 0.107 Uiso 1 1 calc R . . C11 C 1.0898(16) 0.5308(14) 0.2182(4) 0.098(4) Uani 1 1 d . . . H11 H 1.1454 0.5952 0.2350 0.118 Uiso 1 1 calc R . . C12 C 1.1547(12) 0.4497(14) 0.1840(4) 0.093(3) Uani 1 1 d . . . H12 H 1.2558 0.4599 0.1771 0.112 Uiso 1 1 calc R . . C13 C 1.0715(10) 0.3522(11) 0.1594(3) 0.070(3) Uani 1 1 d . . . H13 H 1.1183 0.2959 0.1369 0.084 Uiso 1 1 calc R . . C14 C 0.6307(9) 0.0023(9) 0.4268(3) 0.055(2) Uani 1 1 d . . . C15 C 0.7850(8) 0.0357(9) 0.4059(3) 0.056(2) Uani 1 1 d . . . H15 H 0.7983 0.0307 0.3722 0.067 Uiso 1 1 calc R . . C16 C 0.8966(10) -0.0477(11) 0.4352(3) 0.071(3) Uani 1 1 d . . . H16A H 0.9214 -0.1410 0.4213 0.086 Uiso 1 1 calc R . . H16B H 0.9869 0.0103 0.4361 0.086 Uiso 1 1 calc R . . C17 C 0.7577(10) 0.0465(10) 0.5001(3) 0.069(2) Uani 1 1 d . . . H17A H 0.8266 0.1191 0.5107 0.083 Uiso 1 1 calc R . . H17B H 0.6959 0.0117 0.5264 0.083 Uiso 1 1 calc R . . C18 C 0.6610(9) 0.1187(8) 0.4635(3) 0.0509(19) Uani 1 1 d . . . H18 H 0.5760 0.1771 0.4746 0.061 Uiso 1 1 calc R . . C19 C 0.7612(8) 0.1902(8) 0.4256(3) 0.053(2) Uani 1 1 d . . . H19 H 0.8516 0.2343 0.4369 0.063 Uiso 1 1 calc R . . C20 C 0.7621(10) 0.3609(12) 0.3611(4) 0.080(3) Uani 1 1 d . . . H20A H 0.8074 0.2866 0.3417 0.096 Uiso 1 1 calc R . . H20B H 0.8406 0.4190 0.3736 0.096 Uiso 1 1 calc R . . C21 C 0.6644(9) 0.4587(10) 0.3332(3) 0.060(2) Uani 1 1 d . . . C22 C 0.5731(11) 0.4043(13) 0.2995(4) 0.080(3) Uani 1 1 d . . . H22 H 0.5740 0.3032 0.2944 0.096 Uiso 1 1 calc R . . C23 C 0.4847(12) 0.493(2) 0.2745(4) 0.114(5) Uani 1 1 d . . . H23 H 0.4297 0.4549 0.2511 0.136 Uiso 1 1 calc R . . C24 C 0.4761(16) 0.6453(19) 0.2840(5) 0.114(5) Uani 1 1 d . . . H24 H 0.4109 0.7072 0.2682 0.137 Uiso 1 1 calc R . . C25 C 0.5646(15) 0.7017(13) 0.3170(5) 0.101(4) Uani 1 1 d . . . H25 H 0.5616 0.8025 0.3227 0.121 Uiso 1 1 calc R . . C26 C 0.6568(11) 0.6093(11) 0.3413(3) 0.072(3) Uani 1 1 d . . . H26 H 0.7155 0.6481 0.3637 0.086 Uiso 1 1 calc R . . C27 C 0.8685(9) 0.4833(9) 0.5728(3) 0.0514(19) Uani 1 1 d . . . C28 C 0.8377(9) 0.6077(9) 0.5380(3) 0.055(2) Uani 1 1 d . . . H28 H 0.9220 0.6690 0.5267 0.066 Uiso 1 1 calc R . . C29 C 0.7379(10) 0.5446(10) 0.5015(3) 0.065(2) Uani 1 1 d . . . H29A H 0.6690 0.6208 0.4912 0.078 Uiso 1 1 calc R . . H29B H 0.7989 0.5169 0.4749 0.078 Uiso 1 1 calc R . . C30 C 0.6002(10) 0.4342(11) 0.5655(3) 0.070(3) Uani 1 1 d . . . H30A H 0.5747 0.3370 0.5790 0.083 Uiso 1 1 calc R . . H30B H 0.5105 0.4940 0.5652 0.083 Uiso 1 1 calc R . . C31 C 0.7163(9) 0.5080(9) 0.5953(3) 0.055(2) Uani 1 1 d . . . H31 H 0.7061 0.4912 0.6290 0.066 Uiso 1 1 calc R . . C32 C 0.7389(8) 0.6677(8) 0.5770(3) 0.053(2) Uani 1 1 d . . . H32 H 0.6480 0.7161 0.5664 0.064 Uiso 1 1 calc R . . C33 C 0.7450(11) 0.8143(14) 0.6440(4) 0.093(4) Uani 1 1 d . . . H33A H 0.7124 0.7327 0.6647 0.112 Uiso 1 1 calc R . . H33B H 0.6581 0.8681 0.6338 0.112 Uiso 1 1 calc R . . C34 C 0.8439(9) 0.9154(10) 0.6688(3) 0.064(2) Uani 1 1 d . . . C35 C 0.8512(10) 1.0636(10) 0.6598(3) 0.068(2) Uani 1 1 d . . . H35 H 0.7913 1.1059 0.6373 0.081 Uiso 1 1 calc R . . C36 C 0.9426(14) 1.1530(12) 0.6824(4) 0.092(3) Uani 1 1 d . . . H36 H 0.9423 1.2549 0.6761 0.111 Uiso 1 1 calc R . . C37 C 1.0386(14) 1.0904(15) 0.7159(4) 0.097(4) Uani 1 1 d . . . H37 H 1.1051 1.1491 0.7308 0.116 Uiso 1 1 calc R . . C38 C 1.0301(12) 0.9431(13) 0.7252(4) 0.078(3) Uani 1 1 d . . . H38 H 1.0899 0.9008 0.7477 0.093 Uiso 1 1 calc R . . C39 C 0.9385(11) 0.8553(10) 0.7031(4) 0.072(3) Uani 1 1 d . . . H39 H 0.9367 0.7540 0.7104 0.086 Uiso 1 1 calc R . . C40 C 0.0002(9) 0.1328(9) 0.9279(3) 0.055(2) Uani 1 1 d . . . C41 C 0.0312(9) 0.2860(8) 0.9056(3) 0.053(2) Uani 1 1 d . . . H41 H 0.0234 0.2977 0.8719 0.064 Uiso 1 1 calc R . . C42 C -0.0506(10) 0.3995(10) 0.9356(3) 0.069(2) Uani 1 1 d . . . H42A H 0.0084 0.4890 0.9364 0.082 Uiso 1 1 calc R . . H42B H -0.1446 0.4255 0.9221 0.082 Uiso 1 1 calc R . . C43 C 0.0485(10) 0.2608(10) 0.9998(3) 0.067(2) Uani 1 1 d . . . H43A H 0.0163 0.2002 1.0267 0.080 Uiso 1 1 calc R . . H43B H 0.1217 0.3310 1.0094 0.080 Uiso 1 1 calc R . . C44 C 0.1180(9) 0.1626(9) 0.9633(3) 0.053(2) Uani 1 1 d . . . H44 H 0.1765 0.0774 0.9744 0.064 Uiso 1 1 calc R . . C45 C 0.1888(9) 0.2625(9) 0.9249(3) 0.056(2) Uani 1 1 d . . . H45 H 0.2342 0.3528 0.9358 0.067 Uiso 1 1 calc R . . C46 C 0.3518(13) 0.2622(10) 0.8594(4) 0.088(3) Uani 1 1 d . . . H46A H 0.4069 0.3440 0.8712 0.106 Uiso 1 1 calc R . . H46B H 0.2764 0.3024 0.8393 0.106 Uiso 1 1 calc R . . C47 C 0.4543(9) 0.1616(9) 0.8332(3) 0.057(2) Uani 1 1 d . . . C48 C 0.6043(10) 0.1574(11) 0.8405(4) 0.074(3) Uani 1 1 d . . . H48 H 0.6441 0.2200 0.8616 0.089 Uiso 1 1 calc R . . C49 C 0.6963(14) 0.0621(19) 0.8169(6) 0.122(6) Uani 1 1 d . . . H49 H 0.7966 0.0535 0.8231 0.146 Uiso 1 1 calc R . . C50 C 0.633(3) -0.020(2) 0.7838(6) 0.152(10) Uani 1 1 d . . . H50 H 0.6952 -0.0769 0.7654 0.182 Uiso 1 1 calc R . . C51 C 0.488(3) -0.0237(16) 0.7762(5) 0.128(6) Uani 1 1 d . . . H51 H 0.4491 -0.0885 0.7555 0.153 Uiso 1 1 calc R . . C52 C 0.3989(12) 0.0732(12) 0.8003(4) 0.081(3) Uani 1 1 d . . . H52 H 0.2984 0.0787 0.7942 0.097 Uiso 1 1 calc R . . O1 O 0.4096(8) 0.4705(8) 0.0827(3) 0.089(2) Uani 1 1 d . . . O2 O 0.4212(7) 0.1593(7) 0.0191(2) 0.0763(19) Uani 1 1 d . . . O3 O 0.7670(6) 0.3243(6) 0.1035(2) 0.0619(16) Uani 1 1 d . . . O4 O 0.5276(8) -0.0676(8) 0.4172(3) 0.096(2) Uani 1 1 d . . . O5 O 0.8391(7) -0.0761(7) 0.4814(2) 0.0785(19) Uani 1 1 d . . . O6 O 0.6752(6) 0.2900(6) 0.3981(2) 0.0617(15) Uani 1 1 d . . . O7 O 0.9738(8) 0.4073(8) 0.5814(3) 0.091(2) Uani 1 1 d . . . O8 O 0.6572(7) 0.4193(7) 0.5191(2) 0.0735(18) Uani 1 1 d . . . O9 O 0.8274(6) 0.7582(6) 0.6046(2) 0.0613(16) Uani 1 1 d . . . O10 O -0.0720(8) 0.0299(8) 0.9185(3) 0.090(2) Uani 1 1 d . . . O11 O -0.0766(7) 0.3400(7) 0.9814(2) 0.0753(19) Uani 1 1 d . . . O12 O 0.2847(6) 0.1760(6) 0.8968(2) 0.0625(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.044(4) 0.052(5) 0.065(5) -0.001(4) -0.006(4) 0.004(4) C2 0.050(5) 0.051(5) 0.068(5) -0.001(4) 0.001(4) -0.004(4) C3 0.054(5) 0.066(6) 0.067(6) -0.007(4) -0.009(4) -0.013(4) C4 0.079(6) 0.061(6) 0.092(7) 0.010(5) -0.022(6) -0.019(5) C5 0.065(5) 0.057(5) 0.054(5) 0.008(4) -0.007(4) -0.009(4) C6 0.043(4) 0.048(5) 0.080(6) -0.003(4) -0.012(4) -0.004(4) C7 0.131(9) 0.052(6) 0.096(8) 0.014(5) -0.049(7) -0.019(6) C8 0.074(6) 0.054(5) 0.052(5) 0.011(4) -0.015(4) -0.003(4) C9 0.056(5) 0.077(7) 0.086(7) 0.010(6) 0.002(5) 0.003(5) C10 0.131(11) 0.066(7) 0.072(7) -0.017(5) -0.006(7) -0.006(7) C11 0.115(10) 0.104(9) 0.078(8) -0.005(7) -0.039(7) -0.028(8) C12 0.065(6) 0.115(10) 0.099(9) 0.007(8) -0.017(6) 0.000(6) C13 0.063(6) 0.087(7) 0.061(6) -0.005(5) -0.007(5) 0.011(5) C14 0.052(5) 0.043(4) 0.069(5) 0.003(4) 0.001(4) -0.004(4) C15 0.044(4) 0.061(5) 0.062(5) 0.002(4) 0.011(4) 0.009(4) C16 0.068(6) 0.066(6) 0.078(6) 0.009(5) 0.014(5) 0.019(5) C17 0.070(6) 0.071(6) 0.066(6) 0.010(5) 0.000(5) 0.015(5) C18 0.051(4) 0.046(4) 0.056(5) -0.005(4) 0.002(4) 0.011(4) C19 0.040(4) 0.042(4) 0.076(6) 0.007(4) -0.009(4) 0.000(3) C20 0.050(5) 0.093(7) 0.093(7) 0.030(6) 0.004(5) 0.007(5) C21 0.053(5) 0.074(6) 0.051(5) 0.015(4) 0.011(4) 0.009(4) C22 0.072(6) 0.098(8) 0.070(7) -0.019(6) 0.005(6) -0.003(6) C23 0.064(7) 0.228(19) 0.050(6) -0.004(9) -0.018(5) -0.018(9) C24 0.104(10) 0.118(12) 0.117(11) 0.061(10) -0.005(9) 0.001(9) C25 0.113(10) 0.064(7) 0.122(10) 0.023(7) 0.002(8) -0.007(7) C26 0.082(6) 0.060(6) 0.073(6) 0.014(5) -0.008(5) -0.008(5) C27 0.046(4) 0.042(4) 0.066(5) -0.006(4) 0.001(4) 0.002(4) C28 0.050(4) 0.050(5) 0.064(5) -0.003(4) -0.005(4) -0.004(4) C29 0.064(5) 0.063(6) 0.067(6) -0.007(4) -0.005(4) -0.016(4) C30 0.055(5) 0.069(6) 0.086(7) -0.019(5) 0.011(5) -0.016(4) C31 0.053(5) 0.054(5) 0.058(5) 0.004(4) 0.001(4) -0.003(4) C32 0.037(4) 0.046(4) 0.076(6) -0.007(4) -0.005(4) 0.001(3) C33 0.057(6) 0.119(9) 0.106(8) -0.047(7) 0.019(6) -0.018(6) C34 0.054(5) 0.066(6) 0.072(6) -0.023(5) 0.020(4) -0.002(4) C35 0.069(6) 0.059(6) 0.075(6) -0.004(5) 0.000(5) 0.009(5) C36 0.115(9) 0.051(6) 0.113(9) -0.020(6) -0.006(8) 0.006(6) C37 0.107(9) 0.100(10) 0.086(8) -0.035(7) -0.008(7) -0.005(7) C38 0.075(7) 0.086(8) 0.072(7) 0.002(6) 0.001(5) 0.011(6) C39 0.078(6) 0.050(5) 0.086(7) 0.004(5) 0.017(6) 0.006(5) C40 0.046(4) 0.047(5) 0.072(6) -0.002(4) 0.005(4) -0.003(4) C41 0.055(5) 0.047(5) 0.056(5) 0.004(4) 0.005(4) 0.016(4) C42 0.060(5) 0.063(6) 0.081(7) 0.002(5) 0.011(5) 0.018(4) C43 0.078(6) 0.064(6) 0.057(5) -0.004(4) 0.013(5) 0.016(5) C44 0.053(5) 0.047(5) 0.059(5) 0.002(4) 0.005(4) 0.011(4) C45 0.048(4) 0.041(4) 0.078(6) -0.005(4) 0.016(4) 0.004(3) C46 0.106(8) 0.055(6) 0.099(8) 0.007(5) 0.053(7) 0.011(5) C47 0.059(5) 0.060(5) 0.050(5) 0.010(4) 0.014(4) 0.004(4) C48 0.060(6) 0.075(6) 0.087(7) 0.000(5) 0.006(5) -0.003(5) C49 0.072(8) 0.149(14) 0.135(13) 0.048(11) 0.055(9) 0.037(8) C50 0.22(2) 0.124(14) 0.103(13) 0.040(10) 0.100(15) 0.089(16) C51 0.24(2) 0.072(9) 0.074(8) -0.014(7) 0.009(12) -0.012(12) C52 0.078(7) 0.075(7) 0.090(8) 0.002(6) -0.021(6) -0.002(6) O1 0.078(4) 0.070(4) 0.118(6) 0.000(4) 0.012(4) 0.031(4) O2 0.068(4) 0.087(5) 0.075(4) 0.008(4) -0.027(3) -0.021(3) O3 0.065(4) 0.046(3) 0.076(4) 0.005(3) -0.023(3) -0.004(3) O4 0.087(5) 0.084(5) 0.118(6) -0.024(4) 0.004(4) -0.045(4) O5 0.088(4) 0.066(4) 0.078(4) 0.019(3) 0.013(4) 0.028(3) O6 0.049(3) 0.058(3) 0.077(4) 0.016(3) 0.006(3) 0.008(3) O7 0.073(4) 0.079(5) 0.120(6) 0.006(4) 0.000(4) 0.031(4) O8 0.087(4) 0.065(4) 0.069(4) -0.021(3) 0.004(3) -0.016(3) O9 0.048(3) 0.063(4) 0.073(4) -0.026(3) 0.008(3) -0.004(3) O10 0.088(5) 0.067(4) 0.117(6) -0.003(4) -0.021(4) -0.031(4) O11 0.064(4) 0.085(4) 0.075(4) 0.006(3) 0.024(3) 0.027(3) O12 0.064(3) 0.048(3) 0.073(4) 0.005(3) 0.022(3) 0.014(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.199(10) . ? C1 C5 1.508(12) . ? C1 C2 1.547(11) . ? C2 C6 1.534(11) . ? C2 C3 1.541(11) . ? C2 H2 0.9800 . ? C3 O2 1.421(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 O2 1.420(11) . ? C4 C5 1.567(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.561(11) . ? C5 H5 0.9800 . ? C6 O3 1.432(9) . ? C6 H6 0.9800 . ? C7 O3 1.428(11) . ? C7 C8 1.507(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C13 1.349(13) . ? C8 C9 1.388(13) . ? C9 C10 1.347(14) . ? C9 H9 0.9300 . ? C10 C11 1.351(17) . ? C10 H10 0.9300 . ? C11 C12 1.367(16) . ? C11 H11 0.9300 . ? C12 C13 1.391(15) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O4 1.173(10) . ? C14 C15 1.522(11) . ? C14 C18 1.554(12) . ? C15 C16 1.517(12) . ? C15 C19 1.537(12) . ? C15 H15 0.9800 . ? C16 O5 1.427(10) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O5 1.438(11) . ? C17 C18 1.519(11) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.521(11) . ? C18 H18 0.9800 . ? C19 O6 1.422(9) . ? C19 H19 0.9800 . ? C20 O6 1.435(10) . ? C20 C21 1.481(12) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C26 1.389(13) . ? C21 C22 1.400(13) . ? C22 C23 1.338(17) . ? C22 H22 0.9300 . ? C23 C24 1.41(2) . ? C23 H23 0.9300 . ? C24 C25 1.378(19) . ? C24 H24 0.9300 . ? C25 C26 1.367(15) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 O7 1.197(10) . ? C27 C28 1.508(11) . ? C27 C31 1.517(11) . ? C28 C32 1.526(11) . ? C28 C29 1.537(11) . ? C28 H28 0.9800 . ? C29 O8 1.413(10) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 O8 1.430(10) . ? C30 C31 1.548(12) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.526(11) . ? C31 H31 0.9800 . ? C32 O9 1.429(9) . ? C32 H32 0.9800 . ? C33 O9 1.445(11) . ? C33 C34 1.495(13) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 C35 1.353(13) . ? C34 C39 1.422(14) . ? C35 C36 1.356(14) . ? C35 H35 0.9300 . ? C36 C37 1.419(16) . ? C36 H36 0.9300 . ? C37 C38 1.347(16) . ? C37 H37 0.9300 . ? C38 C39 1.340(14) . ? C38 H38 0.9300 . ? C39 H39 0.9300 . ? C40 O10 1.181(9) . ? C40 C41 1.523(11) . ? C40 C44 1.531(12) . ? C41 C42 1.537(11) . ? C41 C45 1.555(12) . ? C41 H41 0.9800 . ? C42 O11 1.419(11) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 O11 1.440(11) . ? C43 C44 1.521(11) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 C45 1.524(11) . ? C44 H44 0.9800 . ? C45 O12 1.419(9) . ? C45 H45 0.9800 . ? C46 O12 1.423(10) . ? C46 C47 1.501(12) . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C52 1.372(13) . ? C47 C48 1.376(13) . ? C48 C49 1.375(17) . ? C48 H48 0.9300 . ? C49 C50 1.37(3) . ? C49 H49 0.9300 . ? C50 C51 1.33(3) . ? C50 H50 0.9300 . ? C51 C52 1.38(2) . ? C51 H51 0.9300 . ? C52 H52 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 O1 C1 C5 136.6(8) . . ? O1 C1 C2 134.1(8) . . ? C5 C1 C2 88.9(6) . . ? C6 C2 C3 108.6(7) . . ? C6 C2 C1 84.7(6) . . ? C3 C2 C1 107.3(6) . . ? C6 C2 H2 117.2 . . ? C3 C2 H2 117.2 . . ? C1 C2 H2 117.2 . . ? O2 C3 C2 110.5(7) . . ? O2 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? O2 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? O2 C4 C5 110.5(7) . . ? O2 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? O2 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C1 C5 C6 85.1(6) . . ? C1 C5 C4 107.3(7) . . ? C6 C5 C4 106.1(7) . . ? C1 C5 H5 117.8 . . ? C6 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? O3 C6 C2 108.7(6) . . ? O3 C6 C5 114.0(7) . . ? C2 C6 C5 87.4(6) . . ? O3 C6 H6 114.6 . . ? C2 C6 H6 114.6 . . ? C5 C6 H6 114.6 . . ? O3 C7 C8 108.3(7) . . ? O3 C7 H7A 110.0 . . ? C8 C7 H7A 110.0 . . ? O3 C7 H7B 110.0 . . ? C8 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? C13 C8 C9 116.8(9) . . ? C13 C8 C7 122.0(10) . . ? C9 C8 C7 121.2(9) . . ? C10 C9 C8 122.1(10) . . ? C10 C9 H9 119.0 . . ? C8 C9 H9 119.0 . . ? C9 C10 C11 121.3(11) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C12 117.9(11) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? C11 C12 C13 120.9(11) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C8 C13 C12 121.0(10) . . ? C8 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? O4 C14 C15 136.8(9) . . ? O4 C14 C18 135.1(8) . . ? C15 C14 C18 87.7(6) . . ? C16 C15 C14 107.9(7) . . ? C16 C15 C19 108.3(7) . . ? C14 C15 C19 84.8(6) . . ? C16 C15 H15 117.1 . . ? C14 C15 H15 117.1 . . ? C19 C15 H15 117.1 . . ? O5 C16 C15 111.3(7) . . ? O5 C16 H16A 109.4 . . ? C15 C16 H16A 109.4 . . ? O5 C16 H16B 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? O5 C17 C18 110.5(7) . . ? O5 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? O5 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C19 108.6(7) . . ? C17 C18 C14 108.2(7) . . ? C19 C18 C14 84.3(6) . . ? C17 C18 H18 117.0 . . ? C19 C18 H18 117.0 . . ? C14 C18 H18 117.0 . . ? O6 C19 C18 108.8(6) . . ? O6 C19 C15 115.3(7) . . ? C18 C19 C15 88.4(6) . . ? O6 C19 H19 113.9 . . ? C18 C19 H19 113.9 . . ? C15 C19 H19 113.9 . . ? O6 C20 C21 109.0(7) . . ? O6 C20 H20A 109.9 . . ? C21 C20 H20A 109.9 . . ? O6 C20 H20B 109.9 . . ? C21 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? C26 C21 C22 117.7(9) . . ? C26 C21 C20 119.8(9) . . ? C22 C21 C20 122.4(10) . . ? C23 C22 C21 122.2(12) . . ? C23 C22 H22 118.9 . . ? C21 C22 H22 118.9 . . ? C22 C23 C24 119.1(12) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C25 C24 C23 119.8(12) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C26 C25 C24 119.9(12) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C21 121.2(10) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? O7 C27 C28 135.0(8) . . ? O7 C27 C31 135.5(8) . . ? C28 C27 C31 89.2(6) . . ? C27 C28 C32 84.2(6) . . ? C27 C28 C29 107.2(7) . . ? C32 C28 C29 108.5(7) . . ? C27 C28 H28 117.3 . . ? C32 C28 H28 117.3 . . ? C29 C28 H28 117.3 . . ? O8 C29 C28 112.0(7) . . ? O8 C29 H29A 109.2 . . ? C28 C29 H29A 109.2 . . ? O8 C29 H29B 109.2 . . ? C28 C29 H29B 109.2 . . ? H29A C29 H29B 107.9 . . ? O8 C30 C31 110.7(7) . . ? O8 C30 H30A 109.5 . . ? C31 C30 H30A 109.5 . . ? O8 C30 H30B 109.5 . . ? C31 C30 H30B 109.5 . . ? H30A C30 H30B 108.1 . . ? C27 C31 C32 83.9(6) . . ? C27 C31 C30 107.9(7) . . ? C32 C31 C30 108.3(7) . . ? C27 C31 H31 117.3 . . ? C32 C31 H31 117.3 . . ? C30 C31 H31 117.3 . . ? O9 C32 C31 115.4(7) . . ? O9 C32 C28 108.5(6) . . ? C31 C32 C28 88.2(6) . . ? O9 C32 H32 114.0 . . ? C31 C32 H32 114.0 . . ? C28 C32 H32 114.0 . . ? O9 C33 C34 108.5(7) . . ? O9 C33 H33A 110.0 . . ? C34 C33 H33A 110.0 . . ? O9 C33 H33B 110.0 . . ? C34 C33 H33B 110.0 . . ? H33A C33 H33B 108.4 . . ? C35 C34 C39 116.8(9) . . ? C35 C34 C33 123.6(10) . . ? C39 C34 C33 119.6(10) . . ? C34 C35 C36 122.6(10) . . ? C34 C35 H35 118.7 . . ? C36 C35 H35 118.7 . . ? C35 C36 C37 119.7(10) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C38 C37 C36 117.8(11) . . ? C38 C37 H37 121.1 . . ? C36 C37 H37 121.1 . . ? C39 C38 C37 122.3(11) . . ? C39 C38 H38 118.8 . . ? C37 C38 H38 118.8 . . ? C38 C39 C34 120.8(9) . . ? C38 C39 H39 119.6 . . ? C34 C39 H39 119.6 . . ? O10 C40 C41 134.9(9) . . ? O10 C40 C44 135.8(8) . . ? C41 C40 C44 88.8(6) . . ? C40 C41 C42 107.2(7) . . ? C40 C41 C45 84.2(6) . . ? C42 C41 C45 107.8(7) . . ? C40 C41 H41 117.5 . . ? C42 C41 H41 117.5 . . ? C45 C41 H41 117.5 . . ? O11 C42 C41 110.5(7) . . ? O11 C42 H42A 109.6 . . ? C41 C42 H42A 109.6 . . ? O11 C42 H42B 109.6 . . ? C41 C42 H42B 109.6 . . ? H42A C42 H42B 108.1 . . ? O11 C43 C44 110.1(7) . . ? O11 C43 H43A 109.6 . . ? C44 C43 H43A 109.6 . . ? O11 C43 H43B 109.6 . . ? C44 C43 H43B 109.6 . . ? H43A C43 H43B 108.1 . . ? C43 C44 C45 108.2(7) . . ? C43 C44 C40 107.9(7) . . ? C45 C44 C40 85.0(6) . . ? C43 C44 H44 117.1 . . ? C45 C44 H44 117.1 . . ? C40 C44 H44 117.1 . . ? O12 C45 C44 109.0(6) . . ? O12 C45 C41 114.1(7) . . ? C44 C45 C41 87.9(6) . . ? O12 C45 H45 114.3 . . ? C44 C45 H45 114.3 . . ? C41 C45 H45 114.3 . . ? O12 C46 C47 107.4(7) . . ? O12 C46 H46A 110.2 . . ? C47 C46 H46A 110.2 . . ? O12 C46 H46B 110.2 . . ? C47 C46 H46B 110.2 . . ? H46A C46 H46B 108.5 . . ? C52 C47 C48 118.6(9) . . ? C52 C47 C46 119.8(9) . . ? C48 C47 C46 121.6(9) . . ? C49 C48 C47 121.0(12) . . ? C49 C48 H48 119.5 . . ? C47 C48 H48 119.5 . . ? C50 C49 C48 116.6(14) . . ? C50 C49 H49 121.7 . . ? C48 C49 H49 121.7 . . ? C51 C50 C49 124.9(15) . . ? C51 C50 H50 117.5 . . ? C49 C50 H50 117.5 . . ? C50 C51 C52 116.7(15) . . ? C50 C51 H51 121.7 . . ? C52 C51 H51 121.7 . . ? C47 C52 C51 121.8(12) . . ? C47 C52 H52 119.1 . . ? C51 C52 H52 119.1 . . ? C4 O2 C3 113.3(6) . . ? C7 O3 C6 111.8(6) . . ? C16 O5 C17 113.6(7) . . ? C19 O6 C20 112.1(6) . . ? C29 O8 C30 113.4(6) . . ? C32 O9 C33 112.6(6) . . ? C42 O11 C43 113.7(6) . . ? C45 O12 C46 111.9(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C6 145.1(11) . . . . ? C5 C1 C2 C6 -28.1(6) . . . . ? O1 C1 C2 C3 -107.1(11) . . . . ? C5 C1 C2 C3 79.8(7) . . . . ? C6 C2 C3 O2 67.5(9) . . . . ? C1 C2 C3 O2 -22.7(9) . . . . ? O1 C1 C5 C6 -145.3(11) . . . . ? C2 C1 C5 C6 27.5(6) . . . . ? O1 C1 C5 C4 109.3(12) . . . . ? C2 C1 C5 C4 -77.8(7) . . . . ? O2 C4 C5 C1 21.2(10) . . . . ? O2 C4 C5 C6 -68.6(9) . . . . ? C3 C2 C6 O3 166.0(6) . . . . ? C1 C2 C6 O3 -87.5(7) . . . . ? C3 C2 C6 C5 -79.4(7) . . . . ? C1 C2 C6 C5 27.1(6) . . . . ? C1 C5 C6 O3 81.6(7) . . . . ? C4 C5 C6 O3 -171.8(6) . . . . ? C1 C5 C6 C2 -27.8(6) . . . . ? C4 C5 C6 C2 78.8(7) . . . . ? O3 C7 C8 C13 -95.2(11) . . . . ? O3 C7 C8 C9 83.7(11) . . . . ? C13 C8 C9 C10 -0.4(14) . . . . ? C7 C8 C9 C10 -179.4(9) . . . . ? C8 C9 C10 C11 1.6(17) . . . . ? C9 C10 C11 C12 -1.0(18) . . . . ? C10 C11 C12 C13 -0.7(18) . . . . ? C9 C8 C13 C12 -1.4(14) . . . . ? C7 C8 C13 C12 177.7(9) . . . . ? C11 C12 C13 C8 2.0(16) . . . . ? O4 C14 C15 C16 -107.6(12) . . . . ? C18 C14 C15 C16 79.5(7) . . . . ? O4 C14 C15 C19 144.8(12) . . . . ? C18 C14 C15 C19 -28.2(6) . . . . ? C14 C15 C16 O5 -25.0(10) . . . . ? C19 C15 C16 O5 65.5(9) . . . . ? O5 C17 C18 C19 -66.6(9) . . . . ? O5 C17 C18 C14 23.4(9) . . . . ? O4 C14 C18 C17 107.6(12) . . . . ? C15 C14 C18 C17 -79.2(7) . . . . ? O4 C14 C18 C19 -144.6(11) . . . . ? C15 C14 C18 C19 28.5(6) . . . . ? C17 C18 C19 O6 -164.6(7) . . . . ? C14 C18 C19 O6 88.0(7) . . . . ? C17 C18 C19 C15 79.1(7) . . . . ? C14 C18 C19 C15 -28.2(6) . . . . ? C16 C15 C19 O6 171.7(6) . . . . ? C14 C15 C19 O6 -81.2(7) . . . . ? C16 C15 C19 C18 -78.3(7) . . . . ? C14 C15 C19 C18 28.8(6) . . . . ? O6 C20 C21 C26 97.0(10) . . . . ? O6 C20 C21 C22 -80.4(11) . . . . ? C26 C21 C22 C23 2.4(14) . . . . ? C20 C21 C22 C23 179.8(9) . . . . ? C21 C22 C23 C24 -3.9(17) . . . . ? C22 C23 C24 C25 3.7(19) . . . . ? C23 C24 C25 C26 -2.1(19) . . . . ? C24 C25 C26 C21 0.6(17) . . . . ? C22 C21 C26 C25 -0.7(14) . . . . ? C20 C21 C26 C25 -178.2(9) . . . . ? O7 C27 C28 C32 -145.5(11) . . . . ? C31 C27 C28 C32 28.4(6) . . . . ? O7 C27 C28 C29 106.9(11) . . . . ? C31 C27 C28 C29 -79.2(7) . . . . ? C27 C28 C29 O8 23.9(9) . . . . ? C32 C28 C29 O8 -65.6(9) . . . . ? O7 C27 C31 C32 145.4(11) . . . . ? C28 C27 C31 C32 -28.5(6) . . . . ? O7 C27 C31 C30 -107.3(12) . . . . ? C28 C27 C31 C30 78.8(7) . . . . ? O8 C30 C31 C27 -22.9(10) . . . . ? O8 C30 C31 C32 66.5(9) . . . . ? C27 C31 C32 O9 -81.5(7) . . . . ? C30 C31 C32 O9 171.7(6) . . . . ? C27 C31 C32 C28 28.1(6) . . . . ? C30 C31 C32 C28 -78.7(7) . . . . ? C27 C28 C32 O9 88.0(7) . . . . ? C29 C28 C32 O9 -165.8(6) . . . . ? C27 C28 C32 C31 -28.3(6) . . . . ? C29 C28 C32 C31 78.0(7) . . . . ? O9 C33 C34 C35 92.0(11) . . . . ? O9 C33 C34 C39 -86.9(11) . . . . ? C39 C34 C35 C36 -0.6(14) . . . . ? C33 C34 C35 C36 -179.5(9) . . . . ? C34 C35 C36 C37 2.1(16) . . . . ? C35 C36 C37 C38 -2.8(17) . . . . ? C36 C37 C38 C39 2.1(17) . . . . ? C37 C38 C39 C34 -0.7(15) . . . . ? C35 C34 C39 C38 -0.2(13) . . . . ? C33 C34 C39 C38 178.8(8) . . . . ? O10 C40 C41 C42 108.1(11) . . . . ? C44 C40 C41 C42 -79.2(7) . . . . ? O10 C40 C41 C45 -145.0(11) . . . . ? C44 C40 C41 C45 27.7(6) . . . . ? C40 C41 C42 O11 23.0(10) . . . . ? C45 C41 C42 O11 -66.2(9) . . . . ? O11 C43 C44 C45 68.1(9) . . . . ? O11 C43 C44 C40 -22.5(9) . . . . ? O10 C40 C44 C43 -108.2(11) . . . . ? C41 C40 C44 C43 79.2(7) . . . . ? O10 C40 C44 C45 144.3(11) . . . . ? C41 C40 C44 C45 -28.3(5) . . . . ? C43 C44 C45 O12 165.6(7) . . . . ? C40 C44 C45 O12 -87.2(7) . . . . ? C43 C44 C45 C41 -79.6(7) . . . . ? C40 C44 C45 C41 27.6(6) . . . . ? C40 C41 C45 O12 82.1(7) . . . . ? C42 C41 C45 O12 -171.7(6) . . . . ? C40 C41 C45 C44 -27.8(6) . . . . ? C42 C41 C45 C44 78.4(7) . . . . ? O12 C46 C47 C52 83.5(11) . . . . ? O12 C46 C47 C48 -97.8(11) . . . . ? C52 C47 C48 C49 -2.9(15) . . . . ? C46 C47 C48 C49 178.4(10) . . . . ? C47 C48 C49 C50 4.5(18) . . . . ? C48 C49 C50 C51 -7(2) . . . . ? C49 C50 C51 C52 7(2) . . . . ? C48 C47 C52 C51 2.9(15) . . . . ? C46 C47 C52 C51 -178.3(10) . . . . ? C50 C51 C52 C47 -5(2) . . . . ? C5 C4 O2 C3 45.1(11) . . . . ? C2 C3 O2 C4 -43.6(10) . . . . ? C8 C7 O3 C6 179.8(8) . . . . ? C2 C6 O3 C7 179.4(8) . . . . ? C5 C6 O3 C7 83.7(9) . . . . ? C15 C16 O5 C17 -41.0(11) . . . . ? C18 C17 O5 C16 41.0(10) . . . . ? C18 C19 O6 C20 -179.3(7) . . . . ? C15 C19 O6 C20 -82.0(9) . . . . ? C21 C20 O6 C19 178.0(8) . . . . ? C28 C29 O8 C30 40.9(10) . . . . ? C31 C30 O8 C29 -41.0(10) . . . . ? C31 C32 O9 C33 -80.1(9) . . . . ? C28 C32 O9 C33 -177.1(8) . . . . ? C34 C33 O9 C32 -176.2(8) . . . . ? C41 C42 O11 C43 42.9(10) . . . . ? C44 C43 O11 C42 -43.2(10) . . . . ? C44 C45 O12 C46 178.5(8) . . . . ? C41 C45 O12 C46 82.1(9) . . . . ? C47 C46 O12 C45 178.0(8) . . . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.441 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.089 # Attachment '- product 13d .cif' data_p21c1 _database_code_depnum_ccdc_archive 'CCDC 855320' #TrackingRef '- product 13d .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 O2 S2' _chemical_formula_weight 306.42 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' 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 P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.089(2) _cell_length_b 15.631(5) _cell_length_c 13.579(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.518(3) _cell_angle_gamma 90.00 _cell_volume 1503.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4758 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 28.20 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9233 _exptl_absorpt_correction_T_max 0.9361 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10095 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0252 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 25.49 _reflns_number_total 2787 _reflns_number_gt 2325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0637P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.053(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2787 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0359 _refine_ls_wR_factor_ref 0.1346 _refine_ls_wR_factor_gt 0.1187 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.6236(3) 0.53642(13) 0.31549(16) 0.0460(5) Uani 1 1 d . . . H1 H 0.6351 0.5225 0.3821 0.055 Uiso 1 1 calc R . . C2 C 0.7428(3) 0.59677(15) 0.27767(18) 0.0545(6) Uani 1 1 d . . . H2 H 0.8337 0.6230 0.3189 0.065 Uiso 1 1 calc R . . C3 C 0.7280(3) 0.61826(15) 0.18001(19) 0.0628(7) Uani 1 1 d . . . H3 H 0.8076 0.6593 0.1548 0.075 Uiso 1 1 calc R . . C4 C 0.5938(4) 0.57841(18) 0.1191(2) 0.0735(8) Uani 1 1 d . . . H4 H 0.5846 0.5918 0.0524 0.088 Uiso 1 1 calc R . . C5 C 0.4727(3) 0.51844(16) 0.15729(17) 0.0588(6) Uani 1 1 d . . . H5 H 0.3807 0.4929 0.1161 0.071 Uiso 1 1 calc R . . C6 C 0.4870(2) 0.49620(12) 0.25562(14) 0.0375(4) Uani 1 1 d . . . C7 C 0.3557(2) 0.42900(11) 0.29378(13) 0.0341(4) Uani 1 1 d . . . H7 H 0.3618 0.3748 0.2579 0.041 Uiso 1 1 calc R . . C8 C 0.3570(3) 0.41681(12) 0.40754(13) 0.0402(5) Uani 1 1 d . . . H8 H 0.4770 0.4264 0.4444 0.048 Uiso 1 1 calc R . . C9 C 0.2147(3) 0.48887(12) 0.40622(14) 0.0392(4) Uani 1 1 d . . . C10 C 0.1484(2) 0.46254(11) 0.30268(13) 0.0343(4) Uani 1 1 d . . . H10 H 0.1067 0.5084 0.2575 0.041 Uiso 1 1 calc R . . C11 C 0.0124(2) 0.38604(11) 0.31385(13) 0.0350(4) Uani 1 1 d . . . H11 H -0.0815 0.4018 0.3615 0.042 Uiso 1 1 calc R . . C12 C 0.2502(3) 0.33395(12) 0.42907(15) 0.0472(5) Uani 1 1 d . . . H12A H 0.3397 0.2873 0.4373 0.057 Uiso 1 1 calc R . . H12B H 0.1858 0.3403 0.4902 0.057 Uiso 1 1 calc R . . C13 C -0.0914(2) 0.36041(12) 0.21786(13) 0.0360(4) Uani 1 1 d . . . H13 H -0.1760 0.4078 0.1990 0.043 Uiso 1 1 calc R . . C14 C -0.1204(3) 0.33324(16) 0.02039(16) 0.0558(6) Uani 1 1 d . . . H14A H -0.1941 0.3855 0.0172 0.067 Uiso 1 1 calc R . . H14B H -0.0615 0.3266 -0.0423 0.067 Uiso 1 1 calc R . . C15 C -0.2516(3) 0.25875(16) 0.03464(18) 0.0581(6) Uani 1 1 d . . . H15A H -0.3343 0.2529 -0.0238 0.070 Uiso 1 1 calc R . . H15B H -0.1771 0.2068 0.0411 0.070 Uiso 1 1 calc R . . C16 C -0.3709(3) 0.26692(16) 0.12316(17) 0.0584(6) Uani 1 1 d . . . H16A H -0.4592 0.2195 0.1231 0.070 Uiso 1 1 calc R . . H16B H -0.4440 0.3193 0.1170 0.070 Uiso 1 1 calc R . . O1 O 0.1801(2) 0.54673(10) 0.46020(11) 0.0552(4) Uani 1 1 d . . . O2 O 0.11568(18) 0.31375(8) 0.35141(10) 0.0432(4) Uani 1 1 d . . . S1 S 0.06282(7) 0.34397(4) 0.11688(4) 0.0519(2) Uani 1 1 d . . . S2 S -0.23871(8) 0.26831(4) 0.24001(4) 0.0549(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0392(10) 0.0531(12) 0.0460(11) -0.0085(9) 0.0046(8) -0.0040(8) C2 0.0415(11) 0.0525(13) 0.0701(15) -0.0124(11) 0.0079(10) -0.0071(9) C3 0.0530(13) 0.0499(13) 0.0861(18) 0.0154(12) 0.0118(12) -0.0068(10) C4 0.0799(17) 0.0800(18) 0.0603(16) 0.0285(13) 0.0000(13) -0.0124(14) C5 0.0612(14) 0.0638(15) 0.0503(13) 0.0118(11) -0.0096(11) -0.0122(11) C6 0.0340(9) 0.0373(10) 0.0412(10) -0.0026(8) 0.0021(8) 0.0062(7) C7 0.0321(9) 0.0345(9) 0.0354(9) -0.0041(7) -0.0028(7) 0.0032(7) C8 0.0390(10) 0.0435(11) 0.0374(10) 0.0001(8) -0.0064(8) -0.0025(8) C9 0.0425(10) 0.0378(10) 0.0373(10) -0.0031(8) 0.0026(8) -0.0054(8) C10 0.0347(9) 0.0322(9) 0.0358(9) -0.0013(7) -0.0004(7) 0.0043(7) C11 0.0342(9) 0.0352(10) 0.0355(9) -0.0021(7) 0.0013(7) 0.0040(7) C12 0.0509(11) 0.0436(11) 0.0456(12) 0.0071(9) -0.0140(9) -0.0032(9) C13 0.0294(8) 0.0405(10) 0.0382(10) -0.0036(8) 0.0022(7) 0.0009(7) C14 0.0480(12) 0.0808(16) 0.0387(12) -0.0127(10) 0.0014(9) -0.0076(11) C15 0.0530(13) 0.0665(15) 0.0540(13) -0.0205(11) -0.0064(10) -0.0050(11) C16 0.0465(12) 0.0719(16) 0.0559(13) -0.0089(11) -0.0060(10) -0.0197(11) O1 0.0693(10) 0.0487(9) 0.0480(9) -0.0169(7) 0.0062(7) -0.0013(7) O2 0.0462(7) 0.0346(7) 0.0477(8) 0.0032(6) -0.0109(6) -0.0015(6) S1 0.0339(3) 0.0786(5) 0.0435(4) -0.0183(2) 0.0049(2) -0.0052(2) S2 0.0553(4) 0.0600(4) 0.0488(4) 0.0035(2) -0.0034(3) -0.0204(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.380(3) . ? C1 C6 1.388(3) . ? C1 H1 0.9300 . ? C2 C3 1.368(3) . ? C2 H2 0.9300 . ? C3 C4 1.381(4) . ? C3 H3 0.9300 . ? C4 C5 1.387(3) . ? C4 H4 0.9300 . ? C5 C6 1.379(3) . ? C5 H5 0.9300 . ? C6 C7 1.510(3) . ? C7 C8 1.556(2) . ? C7 C10 1.570(2) . ? C7 H7 0.9800 . ? C8 C9 1.511(3) . ? C8 C12 1.535(3) . ? C8 H8 0.9800 . ? C9 O1 1.196(2) . ? C9 C10 1.520(2) . ? C10 C11 1.548(2) . ? C10 H10 0.9800 . ? C11 O2 1.428(2) . ? C11 C13 1.522(2) . ? C11 H11 0.9800 . ? C12 O2 1.426(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 S1 1.8091(19) . ? C13 S2 1.8115(19) . ? C13 H13 0.9800 . ? C14 C15 1.508(3) . ? C14 S1 1.812(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.505(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 S2 1.807(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.0(2) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 120.4(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.4(2) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 120.2(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C1 118.22(19) . . ? C5 C6 C7 119.16(17) . . ? C1 C6 C7 122.62(18) . . ? C6 C7 C8 116.68(15) . . ? C6 C7 C10 112.79(14) . . ? C8 C7 C10 85.93(13) . . ? C6 C7 H7 112.9 . . ? C8 C7 H7 112.9 . . ? C10 C7 H7 112.9 . . ? C9 C8 C12 107.26(16) . . ? C9 C8 C7 85.54(13) . . ? C12 C8 C7 108.13(15) . . ? C9 C8 H8 117.1 . . ? C12 C8 H8 117.1 . . ? C7 C8 H8 117.1 . . ? O1 C9 C8 135.30(18) . . ? O1 C9 C10 135.10(19) . . ? C8 C9 C10 89.33(14) . . ? C9 C10 C11 106.69(14) . . ? C9 C10 C7 84.79(13) . . ? C11 C10 C7 109.81(14) . . ? C9 C10 H10 117.0 . . ? C11 C10 H10 117.0 . . ? C7 C10 H10 117.0 . . ? O2 C11 C13 108.57(14) . . ? O2 C11 C10 109.54(14) . . ? C13 C11 C10 113.53(15) . . ? O2 C11 H11 108.4 . . ? C13 C11 H11 108.4 . . ? C10 C11 H11 108.4 . . ? O2 C12 C8 111.43(15) . . ? O2 C12 H12A 109.3 . . ? C8 C12 H12A 109.3 . . ? O2 C12 H12B 109.3 . . ? C8 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? C11 C13 S1 113.65(12) . . ? C11 C13 S2 109.12(13) . . ? S1 C13 S2 112.65(10) . . ? C11 C13 H13 107.0 . . ? S1 C13 H13 107.0 . . ? S2 C13 H13 107.0 . . ? C15 C14 S1 113.91(16) . . ? C15 C14 H14A 108.8 . . ? S1 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? S1 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 114.11(19) . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 S2 114.46(16) . . ? C15 C16 H16A 108.6 . . ? S2 C16 H16A 108.6 . . ? C15 C16 H16B 108.6 . . ? S2 C16 H16B 108.6 . . ? H16A C16 H16B 107.6 . . ? C12 O2 C11 113.87(14) . . ? C13 S1 C14 97.10(10) . . ? C16 S2 C13 98.30(10) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.1(3) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 1.3(4) . . . . ? C3 C4 C5 C6 -1.5(4) . . . . ? C4 C5 C6 C1 1.0(3) . . . . ? C4 C5 C6 C7 -178.5(2) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? C2 C1 C6 C7 179.14(18) . . . . ? C5 C6 C7 C8 -170.75(18) . . . . ? C1 C6 C7 C8 9.8(3) . . . . ? C5 C6 C7 C10 -73.6(2) . . . . ? C1 C6 C7 C10 106.96(19) . . . . ? C6 C7 C8 C9 85.72(16) . . . . ? C10 C7 C8 C9 -27.78(12) . . . . ? C6 C7 C8 C12 -167.56(15) . . . . ? C10 C7 C8 C12 78.94(16) . . . . ? C12 C8 C9 O1 106.8(3) . . . . ? C7 C8 C9 O1 -145.6(2) . . . . ? C12 C8 C9 C10 -78.90(16) . . . . ? C7 C8 C9 C10 28.71(13) . . . . ? O1 C9 C10 C11 -105.0(2) . . . . ? C8 C9 C10 C11 80.67(15) . . . . ? O1 C9 C10 C7 145.9(2) . . . . ? C8 C9 C10 C7 -28.47(13) . . . . ? C6 C7 C10 C9 -89.63(16) . . . . ? C8 C7 C10 C9 27.65(12) . . . . ? C6 C7 C10 C11 164.48(14) . . . . ? C8 C7 C10 C11 -78.23(15) . . . . ? C9 C10 C11 O2 -67.52(18) . . . . ? C7 C10 C11 O2 22.89(19) . . . . ? C9 C10 C11 C13 170.94(15) . . . . ? C7 C10 C11 C13 -98.65(17) . . . . ? C9 C8 C12 O2 64.9(2) . . . . ? C7 C8 C12 O2 -26.0(2) . . . . ? O2 C11 C13 S1 -70.72(17) . . . . ? C10 C11 C13 S1 51.35(18) . . . . ? O2 C11 C13 S2 55.91(17) . . . . ? C10 C11 C13 S2 177.99(12) . . . . ? S1 C14 C15 C16 65.9(2) . . . . ? C14 C15 C16 S2 -64.0(3) . . . . ? C8 C12 O2 C11 -41.8(2) . . . . ? C13 C11 O2 C12 167.18(15) . . . . ? C10 C11 O2 C12 42.7(2) . . . . ? C11 C13 S1 C14 -171.23(14) . . . . ? S2 C13 S1 C14 64.01(12) . . . . ? C15 C14 S1 C13 -61.39(18) . . . . ? C15 C16 S2 C13 58.30(19) . . . . ? C11 C13 S2 C16 169.85(14) . . . . ? S1 C13 S2 C16 -62.94(12) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.225 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.041 # Attachment '- product 12d.cif' data_pna21 _database_code_depnum_ccdc_archive 'CCDC 855321' #TrackingRef '- product 12d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O2' _chemical_formula_weight 264.31 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 19.372(13) _cell_length_b 5.761(4) _cell_length_c 24.488(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2733(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1331 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 18.76 _exptl_crystal_description stick _exptl_crystal_colour colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9813 _exptl_absorpt_correction_T_max 0.9845 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17916 _diffrn_reflns_av_R_equivalents 0.1089 _diffrn_reflns_av_sigmaI/netI 0.1125 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 25.30 _reflns_number_total 4932 _reflns_number_gt 2743 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1703P)^2^+0.2924P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(4) _refine_ls_number_reflns 4932 _refine_ls_number_parameters 361 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1562 _refine_ls_R_factor_gt 0.0928 _refine_ls_wR_factor_ref 0.2847 _refine_ls_wR_factor_gt 0.2324 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.968 _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 0.2223(4) 0.9728(15) 0.0993(3) 0.058(2) Uani 1 1 d . . . H1 H 0.2245 1.0998 0.1226 0.069 Uiso 1 1 calc R . . C2 C 0.2623(4) 0.9709(17) 0.0532(4) 0.064(2) Uani 1 1 d . . . H2 H 0.2892 1.0998 0.0446 0.077 Uiso 1 1 calc R . . C3 C 0.2632(5) 0.7790(17) 0.0195(4) 0.059(3) Uani 1 1 d . . . H3 H 0.2930 0.7725 -0.0102 0.071 Uiso 1 1 calc R . . C4 C 0.2192(5) 0.5974(16) 0.0306(3) 0.065(2) Uani 1 1 d . . . H4 H 0.2178 0.4699 0.0073 0.078 Uiso 1 1 calc R . . C5 C 0.1775(4) 0.6035(14) 0.0757(3) 0.059(2) Uani 1 1 d . . . H5 H 0.1478 0.4797 0.0823 0.071 Uiso 1 1 calc R . . C6 C 0.1780(5) 0.7886(14) 0.1121(3) 0.043(2) Uani 1 1 d . . . C7 C 0.1381(4) 0.7781(11) 0.1640(3) 0.0369(18) Uani 1 1 d . . . H7 H 0.1010 0.6628 0.1619 0.044 Uiso 1 1 calc R . . C8 C 0.1100(3) 1.0214(12) 0.1854(3) 0.0443(17) Uani 1 1 d . . . H8 H 0.1037 1.1451 0.1583 0.053 Uiso 1 1 calc R . . C9 C 0.1764(3) 1.0221(13) 0.2181(3) 0.0433(17) Uani 1 1 d . . . C10 C 0.1775(4) 0.7580(10) 0.2169(3) 0.0345(18) Uani 1 1 d . . . H10 H 0.2224 0.6800 0.2162 0.041 Uiso 1 1 calc R . . C11 C 0.1271(5) 0.6894(17) 0.2601(3) 0.067(2) Uani 1 1 d . . . H11A H 0.1298 0.5227 0.2652 0.080 Uiso 1 1 calc R . . H11B H 0.1409 0.7616 0.2942 0.080 Uiso 1 1 calc R . . C12 C 0.0504(3) 0.9810(12) 0.2274(3) 0.0423(16) Uani 1 1 d . . . H12 H 0.0544 1.0939 0.2572 0.051 Uiso 1 1 calc R . . C13 C -0.0192(3) 1.0020(12) 0.2016(3) 0.0395(16) Uani 1 1 d . . . C14 C -0.0480(4) 0.8293(15) 0.1708(4) 0.058(2) Uani 1 1 d . . . H14 H -0.0235 0.6922 0.1655 0.070 Uiso 1 1 calc R . . C15 C -0.1121(4) 0.8528(17) 0.1474(3) 0.065(2) Uani 1 1 d . . . H15 H -0.1297 0.7357 0.1252 0.078 Uiso 1 1 calc R . . C16 C -0.1504(4) 1.0512(17) 0.1569(4) 0.071(3) Uani 1 1 d . . . H16 H -0.1936 1.0716 0.1410 0.086 Uiso 1 1 calc R . . C17 C -0.1205(4) 1.2300(14) 0.1933(4) 0.054(2) Uani 1 1 d . . . H17 H -0.1465 1.3591 0.2031 0.065 Uiso 1 1 calc R . . C18 C -0.0588(4) 1.2069(15) 0.2112(4) 0.053(2) Uani 1 1 d . . . H18 H -0.0392 1.3275 0.2311 0.063 Uiso 1 1 calc R . . C19 C 0.4709(4) 0.9801(16) 0.4758(3) 0.058(2) Uani 1 1 d . . . H19 H 0.4706 1.1086 0.4528 0.070 Uiso 1 1 calc R . . C20 C 0.5134(5) 0.9790(17) 0.5220(4) 0.069(2) Uani 1 1 d . . . H20 H 0.5443 1.0993 0.5287 0.083 Uiso 1 1 calc R . . C21 C 0.5076(6) 0.786(2) 0.5585(4) 0.071(3) Uani 1 1 d . . . H21 H 0.5326 0.7850 0.5909 0.085 Uiso 1 1 calc R . . C22 C 0.4667(5) 0.608(2) 0.5463(4) 0.072(3) Uani 1 1 d . . . H22 H 0.4657 0.4792 0.5692 0.087 Uiso 1 1 calc R . . C23 C 0.4254(4) 0.6119(15) 0.4999(3) 0.053(2) Uani 1 1 d . . . H23 H 0.3949 0.4903 0.4935 0.064 Uiso 1 1 calc R . . C24 C 0.4289(4) 0.7898(13) 0.4640(3) 0.0390(19) Uani 1 1 d . . . C25 C 0.3808(4) 0.7813(12) 0.4146(3) 0.0388(18) Uani 1 1 d . . . H25 H 0.3432 0.6684 0.4178 0.047 Uiso 1 1 calc R . . C26 C 0.3580(3) 1.0245(11) 0.3900(3) 0.0387(16) Uani 1 1 d . . . H26 H 0.3506 1.1516 0.4159 0.046 Uiso 1 1 calc R . . C27 C 0.4249(4) 1.0265(16) 0.3582(3) 0.051(2) Uani 1 1 d . . . C28 C 0.4246(5) 0.7633(14) 0.3570(3) 0.047(2) Uani 1 1 d . . . H28 H 0.4693 0.6837 0.3579 0.057 Uiso 1 1 calc R . . C29 C 0.3725(4) 0.6903(18) 0.3118(4) 0.066(3) Uani 1 1 d . . . H29A H 0.3843 0.7667 0.2777 0.079 Uiso 1 1 calc R . . H29B H 0.3751 0.5239 0.3060 0.079 Uiso 1 1 calc R . . C30 C 0.2998(4) 0.9741(14) 0.3493(3) 0.0479(18) Uani 1 1 d . . . H30 H 0.3036 1.0861 0.3193 0.057 Uiso 1 1 calc R . . C31 C 0.2282(3) 0.9987(12) 0.3742(3) 0.0406(17) Uani 1 1 d . . . C32 C 0.1905(4) 1.2051(14) 0.3653(3) 0.047(2) Uani 1 1 d . . . H32 H 0.2083 1.3246 0.3440 0.056 Uiso 1 1 calc R . . C33 C 0.1229(5) 1.2244(15) 0.3908(4) 0.048(2) Uani 1 1 d . . . H33 H 0.0974 1.3606 0.3875 0.058 Uiso 1 1 calc R . . C34 C 0.0980(4) 1.0476(17) 0.4185(4) 0.067(2) Uani 1 1 d . . . H34 H 0.0531 1.0574 0.4317 0.080 Uiso 1 1 calc R . . C35 C 0.1353(4) 0.8483(18) 0.4290(3) 0.069(3) Uani 1 1 d . . . H35 H 0.1164 0.7328 0.4509 0.083 Uiso 1 1 calc R . . C36 C 0.2021(4) 0.8189(16) 0.4066(3) 0.052(2) Uani 1 1 d . . . H36 H 0.2277 0.6852 0.4132 0.063 Uiso 1 1 calc R . . O1 O 0.2157(3) 1.1648(13) 0.2337(3) 0.0718(16) Uani 1 1 d . . . O2 O 0.0556(3) 0.7513(7) 0.2491(3) 0.0512(17) Uani 1 1 d . . . O3 O 0.4604(3) 1.1923(12) 0.3401(2) 0.0641(16) Uani 1 1 d . . . O4 O 0.3060(3) 0.7510(7) 0.32710(19) 0.0394(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.060(5) 0.058(5) 0.056(5) -0.005(4) 0.007(4) -0.001(4) C2 0.048(5) 0.084(6) 0.061(5) 0.004(5) 0.015(4) 0.004(4) C3 0.060(6) 0.087(7) 0.030(4) 0.002(4) 0.010(4) 0.010(5) C4 0.091(6) 0.057(6) 0.047(5) -0.014(4) 0.014(5) 0.016(5) C5 0.079(6) 0.042(5) 0.056(5) -0.006(4) -0.006(4) 0.015(4) C6 0.052(5) 0.058(5) 0.018(4) -0.004(3) -0.012(3) 0.013(4) C7 0.028(4) 0.044(4) 0.038(4) -0.004(3) 0.000(3) -0.015(3) C8 0.045(4) 0.043(4) 0.046(4) 0.002(3) 0.003(3) 0.001(3) C9 0.039(4) 0.051(5) 0.039(4) -0.012(3) -0.004(3) -0.008(3) C10 0.030(4) 0.030(4) 0.043(4) 0.008(3) 0.001(4) 0.007(2) C11 0.077(6) 0.096(6) 0.027(4) -0.003(4) -0.017(4) 0.027(5) C12 0.044(4) 0.039(4) 0.044(4) 0.005(3) 0.004(3) 0.001(3) C13 0.038(4) 0.041(4) 0.039(4) 0.009(3) 0.004(3) -0.001(3) C14 0.057(5) 0.054(4) 0.064(5) -0.014(5) 0.001(4) -0.003(4) C15 0.055(5) 0.072(6) 0.068(6) 0.000(5) -0.006(4) -0.025(5) C16 0.032(4) 0.089(6) 0.094(6) 0.026(6) -0.001(4) 0.000(4) C17 0.036(5) 0.064(6) 0.063(5) 0.014(4) 0.004(4) 0.010(4) C18 0.044(5) 0.063(5) 0.051(5) 0.006(4) 0.001(4) -0.008(4) C19 0.055(5) 0.067(5) 0.053(5) 0.005(4) -0.013(4) 0.006(4) C20 0.069(6) 0.080(6) 0.059(5) 0.002(5) -0.013(4) -0.008(5) C21 0.061(6) 0.112(9) 0.039(5) 0.002(5) -0.010(5) 0.030(6) C22 0.065(6) 0.099(8) 0.052(5) 0.019(5) 0.000(5) 0.015(6) C23 0.042(4) 0.066(5) 0.051(5) -0.003(4) 0.005(4) -0.014(4) C24 0.020(3) 0.044(4) 0.053(5) 0.010(4) -0.005(3) 0.004(3) C25 0.038(4) 0.048(4) 0.031(4) -0.008(3) 0.006(3) 0.017(3) C26 0.043(4) 0.037(4) 0.036(3) -0.003(3) -0.002(3) 0.004(3) C27 0.044(4) 0.071(6) 0.039(4) 0.007(4) 0.000(3) 0.009(4) C28 0.048(5) 0.069(7) 0.024(4) 0.010(3) 0.007(4) 0.017(4) C29 0.042(5) 0.103(7) 0.052(5) -0.047(5) -0.006(4) 0.010(5) C30 0.051(4) 0.057(5) 0.036(4) 0.004(3) -0.004(3) 0.005(4) C31 0.038(4) 0.045(4) 0.039(4) -0.009(3) -0.014(3) -0.007(3) C32 0.047(5) 0.058(5) 0.035(4) 0.005(4) -0.017(4) 0.014(4) C33 0.043(5) 0.061(6) 0.040(4) 0.005(4) 0.001(3) 0.005(4) C34 0.039(4) 0.074(6) 0.087(6) -0.036(5) -0.008(4) 0.006(5) C35 0.053(5) 0.087(7) 0.067(6) -0.024(5) 0.016(4) -0.020(5) C36 0.033(4) 0.081(5) 0.043(4) -0.014(4) -0.006(3) -0.015(4) O1 0.056(4) 0.094(4) 0.065(4) -0.025(4) -0.002(3) -0.006(4) O2 0.041(3) 0.040(4) 0.073(5) 0.012(2) 0.005(3) -0.001(2) O3 0.053(3) 0.097(4) 0.042(3) 0.010(3) -0.001(3) -0.015(3) O4 0.049(3) 0.051(4) 0.018(2) -0.0131(17) -0.004(2) 0.008(2) _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 1.369(11) . ? C1 C6 1.400(11) . ? C1 H1 0.9300 . ? C2 C3 1.380(12) . ? C2 H2 0.9300 . ? C3 C4 1.376(12) . ? C3 H3 0.9300 . ? C4 C5 1.370(12) . ? C4 H4 0.9300 . ? C5 C6 1.389(10) . ? C5 H5 0.9300 . ? C6 C7 1.489(10) . ? C7 C10 1.508(11) . ? C7 C8 1.592(10) . ? C7 H7 0.9800 . ? C8 C9 1.515(9) . ? C8 C12 1.564(9) . ? C8 H8 0.9800 . ? C9 O1 1.185(8) . ? C9 C10 1.522(10) . ? C10 C11 1.493(11) . ? C10 H10 0.9800 . ? C11 O2 1.456(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 O2 1.429(8) . ? C12 C13 1.493(9) . ? C12 H12 0.9800 . ? C13 C14 1.368(10) . ? C13 C18 1.428(10) . ? C14 C15 1.375(12) . ? C14 H14 0.9300 . ? C15 C16 1.383(13) . ? C15 H15 0.9300 . ? C16 C17 1.479(13) . ? C16 H16 0.9300 . ? C17 C18 1.280(12) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.396(11) . ? C19 C20 1.399(12) . ? C19 H19 0.9300 . ? C20 C21 1.431(14) . ? C20 H20 0.9300 . ? C21 C22 1.330(14) . ? C21 H21 0.9300 . ? C22 C23 1.390(12) . ? C22 H22 0.9300 . ? C23 C24 1.352(10) . ? C23 H23 0.9300 . ? C24 C25 1.528(10) . ? C25 C26 1.587(9) . ? C25 C28 1.648(10) . ? C25 H25 0.9800 . ? C26 C27 1.510(10) . ? C26 C30 1.533(9) . ? C26 H26 0.9800 . ? C27 O3 1.259(9) . ? C27 C28 1.516(12) . ? C28 C29 1.556(11) . ? C28 H28 0.9800 . ? C29 O4 1.387(10) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 O4 1.400(9) . ? C30 C31 1.521(9) . ? C30 H30 0.9800 . ? C31 C36 1.400(11) . ? C31 C32 1.412(10) . ? C32 C33 1.455(13) . ? C32 H32 0.9300 . ? C33 C34 1.315(12) . ? C33 H33 0.9300 . ? C34 C35 1.380(12) . ? C34 H34 0.9300 . ? C35 C36 1.417(11) . ? C35 H35 0.9300 . ? C36 H36 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 C2 C1 C6 121.8(8) . . ? C2 C1 H1 119.1 . . ? C6 C1 H1 119.1 . . ? C1 C2 C3 120.4(8) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 118.9(8) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 120.4(8) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 122.2(9) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 116.2(8) . . ? C5 C6 C7 120.8(8) . . ? C1 C6 C7 122.8(7) . . ? C6 C7 C10 118.3(6) . . ? C6 C7 C8 115.0(6) . . ? C10 C7 C8 87.6(5) . . ? C6 C7 H7 111.3 . . ? C10 C7 H7 111.3 . . ? C8 C7 H7 111.3 . . ? C9 C8 C12 106.2(5) . . ? C9 C8 C7 83.4(5) . . ? C12 C8 C7 109.7(5) . . ? C9 C8 H8 117.4 . . ? C12 C8 H8 117.4 . . ? C7 C8 H8 117.4 . . ? O1 C9 C8 136.0(7) . . ? O1 C9 C10 133.7(7) . . ? C8 C9 C10 89.9(6) . . ? C11 C10 C7 107.4(6) . . ? C11 C10 C9 104.0(6) . . ? C7 C10 C9 86.1(5) . . ? C11 C10 H10 118.1 . . ? C7 C10 H10 118.1 . . ? C9 C10 H10 118.1 . . ? O2 C11 C10 115.2(7) . . ? O2 C11 H11A 108.5 . . ? C10 C11 H11A 108.5 . . ? O2 C11 H11B 108.5 . . ? C10 C11 H11B 108.5 . . ? H11A C11 H11B 107.5 . . ? O2 C12 C13 107.2(5) . . ? O2 C12 C8 109.3(5) . . ? C13 C12 C8 112.1(6) . . ? O2 C12 H12 109.4 . . ? C13 C12 H12 109.4 . . ? C8 C12 H12 109.4 . . ? C14 C13 C18 118.1(7) . . ? C14 C13 C12 122.9(7) . . ? C18 C13 C12 118.9(7) . . ? C13 C14 C15 121.8(8) . . ? C13 C14 H14 119.1 . . ? C15 C14 H14 119.1 . . ? C14 C15 C16 119.7(8) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 117.8(7) . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? C18 C17 C16 120.0(8) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C13 122.2(9) . . ? C17 C18 H18 118.9 . . ? C13 C18 H18 118.9 . . ? C24 C19 C20 120.5(8) . . ? C24 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C21 117.5(9) . . ? C19 C20 H20 121.2 . . ? C21 C20 H20 121.2 . . ? C22 C21 C20 120.4(9) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 120.9(9) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 121.0(8) . . ? C24 C23 H23 119.5 . . ? C22 C23 H23 119.5 . . ? C23 C24 C19 119.3(7) . . ? C23 C24 C25 117.4(7) . . ? C19 C24 C25 123.0(7) . . ? C24 C25 C26 116.2(6) . . ? C24 C25 C28 111.5(6) . . ? C26 C25 C28 82.8(5) . . ? C24 C25 H25 114.2 . . ? C26 C25 H25 114.2 . . ? C28 C25 H25 114.2 . . ? C27 C26 C30 107.3(5) . . ? C27 C26 C25 88.0(5) . . ? C30 C26 C25 106.5(6) . . ? C27 C26 H26 117.0 . . ? C30 C26 H26 117.0 . . ? C25 C26 H26 117.0 . . ? O3 C27 C26 131.0(7) . . ? O3 C27 C28 139.0(7) . . ? C26 C27 C28 90.0(6) . . ? C27 C28 C29 106.6(7) . . ? C27 C28 C25 85.6(5) . . ? C29 C28 C25 107.0(7) . . ? C27 C28 H28 117.6 . . ? C29 C28 H28 117.6 . . ? C25 C28 H28 117.6 . . ? O4 C29 C28 110.0(6) . . ? O4 C29 H29A 109.7 . . ? C28 C29 H29A 109.7 . . ? O4 C29 H29B 109.7 . . ? C28 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? O4 C30 C31 108.6(6) . . ? O4 C30 C26 111.3(6) . . ? C31 C30 C26 113.1(5) . . ? O4 C30 H30 107.9 . . ? C31 C30 H30 107.9 . . ? C26 C30 H30 107.9 . . ? C36 C31 C32 121.5(7) . . ? C36 C31 C30 119.2(7) . . ? C32 C31 C30 119.3(7) . . ? C31 C32 C33 117.7(8) . . ? C31 C32 H32 121.2 . . ? C33 C32 H32 121.2 . . ? C34 C33 C32 119.4(8) . . ? C34 C33 H33 120.3 . . ? C32 C33 H33 120.3 . . ? C33 C34 C35 123.3(8) . . ? C33 C34 H34 118.3 . . ? C35 C34 H34 118.3 . . ? C34 C35 C36 120.3(9) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 117.5(9) . . ? C31 C36 H36 121.3 . . ? C35 C36 H36 121.3 . . ? C12 O2 C11 111.3(6) . . ? C29 O4 C30 114.6(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -3.9(13) . . . . ? C1 C2 C3 C4 4.9(13) . . . . ? C2 C3 C4 C5 -2.7(13) . . . . ? C3 C4 C5 C6 -0.7(13) . . . . ? C4 C5 C6 C1 1.8(12) . . . . ? C4 C5 C6 C7 -173.0(7) . . . . ? C2 C1 C6 C5 0.5(11) . . . . ? C2 C1 C6 C7 175.1(7) . . . . ? C5 C6 C7 C10 109.5(8) . . . . ? C1 C6 C7 C10 -64.9(9) . . . . ? C5 C6 C7 C8 -149.0(7) . . . . ? C1 C6 C7 C8 36.6(10) . . . . ? C6 C7 C8 C9 -93.7(6) . . . . ? C10 C7 C8 C9 26.5(5) . . . . ? C6 C7 C8 C12 161.4(6) . . . . ? C10 C7 C8 C12 -78.4(6) . . . . ? C12 C8 C9 O1 -104.2(9) . . . . ? C7 C8 C9 O1 147.1(9) . . . . ? C12 C8 C9 C10 82.5(6) . . . . ? C7 C8 C9 C10 -26.2(5) . . . . ? C6 C7 C10 C11 -165.6(7) . . . . ? C8 C7 C10 C11 77.2(6) . . . . ? C6 C7 C10 C9 91.0(7) . . . . ? C8 C7 C10 C9 -26.3(5) . . . . ? O1 C9 C10 C11 107.1(9) . . . . ? C8 C9 C10 C11 -79.3(6) . . . . ? O1 C9 C10 C7 -145.9(9) . . . . ? C8 C9 C10 C7 27.7(5) . . . . ? C7 C10 C11 O2 -24.3(9) . . . . ? C9 C10 C11 O2 66.0(9) . . . . ? C9 C8 C12 O2 -67.6(7) . . . . ? C7 C8 C12 O2 21.2(7) . . . . ? C9 C8 C12 C13 173.8(6) . . . . ? C7 C8 C12 C13 -97.5(7) . . . . ? O2 C12 C13 C14 -41.7(9) . . . . ? C8 C12 C13 C14 78.3(8) . . . . ? O2 C12 C13 C18 135.8(7) . . . . ? C8 C12 C13 C18 -104.3(7) . . . . ? C18 C13 C14 C15 2.7(12) . . . . ? C12 C13 C14 C15 -179.8(7) . . . . ? C13 C14 C15 C16 -3.0(12) . . . . ? C14 C15 C16 C17 -1.0(12) . . . . ? C15 C16 C17 C18 5.6(13) . . . . ? C16 C17 C18 C13 -6.1(13) . . . . ? C14 C13 C18 C17 2.0(12) . . . . ? C12 C13 C18 C17 -175.5(8) . . . . ? C24 C19 C20 C21 -5.2(12) . . . . ? C19 C20 C21 C22 4.7(14) . . . . ? C20 C21 C22 C23 -4.2(14) . . . . ? C21 C22 C23 C24 4.3(13) . . . . ? C22 C23 C24 C19 -4.7(11) . . . . ? C22 C23 C24 C25 -179.1(7) . . . . ? C20 C19 C24 C23 5.3(11) . . . . ? C20 C19 C24 C25 179.4(7) . . . . ? C23 C24 C25 C26 151.3(7) . . . . ? C19 C24 C25 C26 -22.9(10) . . . . ? C23 C24 C25 C28 -116.3(7) . . . . ? C19 C24 C25 C28 69.5(9) . . . . ? C24 C25 C26 C27 83.7(7) . . . . ? C28 C25 C26 C27 -26.7(6) . . . . ? C24 C25 C26 C30 -168.9(6) . . . . ? C28 C25 C26 C30 80.7(6) . . . . ? C30 C26 C27 O3 99.8(9) . . . . ? C25 C26 C27 O3 -153.6(8) . . . . ? C30 C26 C27 C28 -77.7(6) . . . . ? C25 C26 C27 C28 29.0(5) . . . . ? O3 C27 C28 C29 -98.5(11) . . . . ? C26 C27 C28 C29 78.5(6) . . . . ? O3 C27 C28 C25 155.1(10) . . . . ? C26 C27 C28 C25 -27.9(5) . . . . ? C24 C25 C28 C27 -88.7(7) . . . . ? C26 C25 C28 C27 26.7(5) . . . . ? C24 C25 C28 C29 165.3(7) . . . . ? C26 C25 C28 C29 -79.4(7) . . . . ? C27 C28 C29 O4 -67.0(9) . . . . ? C25 C28 C29 O4 23.4(9) . . . . ? C27 C26 C30 O4 65.1(7) . . . . ? C25 C26 C30 O4 -27.9(7) . . . . ? C27 C26 C30 C31 -172.3(6) . . . . ? C25 C26 C30 C31 94.7(7) . . . . ? O4 C30 C31 C36 45.2(8) . . . . ? C26 C30 C31 C36 -78.9(8) . . . . ? O4 C30 C31 C32 -136.7(7) . . . . ? C26 C30 C31 C32 99.3(7) . . . . ? C36 C31 C32 C33 -0.5(11) . . . . ? C30 C31 C32 C33 -178.6(7) . . . . ? C31 C32 C33 C34 -3.3(12) . . . . ? C32 C33 C34 C35 5.8(13) . . . . ? C33 C34 C35 C36 -4.3(13) . . . . ? C32 C31 C36 C35 1.9(10) . . . . ? C30 C31 C36 C35 -180.0(6) . . . . ? C34 C35 C36 C31 0.3(11) . . . . ? C13 C12 O2 C11 162.7(6) . . . . ? C8 C12 O2 C11 41.0(8) . . . . ? C10 C11 O2 C12 -43.0(10) . . . . ? C28 C29 O4 C30 44.4(10) . . . . ? C31 C30 O4 C29 -169.0(7) . . . . ? C26 C30 O4 C29 -43.9(8) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.517 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.075