data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Dr Kimiaki Yamamura' _publ_contact_author_address ; Faculty of Science Kobe University Rokkodai, Nada, Kobe Hyogo 657-8501 JAPAN ; _publ_contact_author_email KYAMA@KOBE-U.AC.JP _publ_section_title ; An Efficient Novel Synthesis of b-(Azuleno[1,2-b]benzothienyl)- and b-(Azuleno[2,1-b]benzothienyl)-a,b-unsaturated Ketones by the Tropylium-ion Mediated Intramolecular Furan Ring-opening Reaction and X-ray Investigation of Methyl Ketone Derivative ; loop_ _publ_author_name 'Kimiaki Yamamura' 'Masao Hashimoto' 'Yuuko Houda' 'Makoto Kamezawa' 'Takatomo Kimura' 'Takehiko Otani' data_azul-8a _database_code_depnum_ccdc_archive 'CCDC 226170' _audit_creation_method SHELXL-97 _chemical_name_systematic (E)-4-(11-azuleno[2,1-b]benzothiophenyl)-3-butene-2-one _chemical_name_common (E)-4-(11-azuleno(2,1-b)benzothiophenyl)-3-butene-2-one _chemical_melting_point 393K _chemical_formula_moiety 'benzothiophene, azulene, carbonyl' _chemical_formula_sum 'C20 H14 O S' _chemical_formula_weight 302.37 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)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 10.2869(16) _cell_length_b 6.7635(11) _cell_length_c 11.4718(18) _cell_angle_alpha 90.00 _cell_angle_beta 111.162(3) _cell_angle_gamma 90.00 _cell_volume 744.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 289(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour 'dark greenish-brown' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 289(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3962 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 27.09 _reflns_number_total 1608 _reflns_number_gt 1315 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0762P)^2^+0.0493P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1608 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0413 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1100 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.0934(2) 0.2500 0.2865(2) 0.0397(5) Uani 1 2 d S . . C2 C 0.1322(3) 0.2500 0.1826(3) 0.0557(7) Uani 1 2 d S . . C3 C 0.0281(4) 0.2500 0.0659(3) 0.0676(9) Uani 1 2 d S . . C4 C -0.1109(3) 0.2500 0.0527(2) 0.0619(8) Uani 1 2 d S . . C5 C -0.1501(3) 0.2500 0.1559(2) 0.0487(6) Uani 1 2 d S . . C6 C -0.0469(2) 0.2500 0.2764(2) 0.0364(5) Uani 1 2 d S . . C7 C -0.0571(2) 0.2500 0.3984(2) 0.0349(5) Uani 1 2 d S . . C8 C -0.1605(2) 0.2500 0.4524(2) 0.0353(5) Uani 1 2 d S . . C9 C -0.3037(3) 0.2500 0.3890(2) 0.0462(6) Uani 1 2 d S . . C10 C -0.4102(3) 0.2500 0.4365(3) 0.0577(7) Uani 1 2 d S . . C11 C -0.4005(3) 0.2500 0.5599(3) 0.0596(8) Uani 1 2 d S . . C12 C -0.2840(3) 0.2500 0.6675(3) 0.0538(7) Uani 1 2 d S . . C13 C -0.1445(3) 0.2500 0.6814(2) 0.0427(5) Uani 1 2 d S . . C14 C -0.0849(2) 0.2500 0.5905(2) 0.0356(5) Uani 1 2 d S . . C15 C 0.0599(2) 0.2500 0.6137(2) 0.0342(5) Uani 1 2 d S . . C16 C 0.0732(2) 0.2500 0.4951(2) 0.0339(5) Uani 1 2 d S . . C17 C 0.1698(2) 0.2500 0.7339(2) 0.0379(5) Uani 1 2 d S . . C18 C 0.3071(3) 0.2500 0.7564(2) 0.0474(6) Uani 1 2 d S . . C19 C 0.4173(3) 0.2500 0.8800(3) 0.0551(7) Uani 1 2 d S . . C20 C 0.3800(4) 0.2500 0.9946(3) 0.0697(10) Uani 1 2 d S . . H1 H 0.231(3) 0.2500 0.188(3) 0.065(8) Uiso 1 2 d S . . H2 H 0.048(4) 0.2500 -0.007(4) 0.078(10) Uiso 1 2 d S . . H3 H -0.180(3) 0.2500 -0.023(3) 0.063(9) Uiso 1 2 d S . . H4 H -0.248(3) 0.2500 0.146(3) 0.050(7) Uiso 1 2 d S . . H5 H -0.336(3) 0.2500 0.298(3) 0.054(8) Uiso 1 2 d S . . H6 H -0.509(4) 0.2500 0.378(3) 0.066(9) Uiso 1 2 d S . . H7 H -0.482(3) 0.2500 0.574(2) 0.054(8) Uiso 1 2 d S . . H8 H -0.299(3) 0.2500 0.745(3) 0.070(9) Uiso 1 2 d S . . H9 H -0.081(3) 0.2500 0.762(2) 0.042(7) Uiso 1 2 d S . . H10 H 0.143(3) 0.2500 0.801(3) 0.054(8) Uiso 1 2 d S . . H11 H 0.347(3) 0.2500 0.685(3) 0.061(8) Uiso 1 2 d S . . H12 H 0.331(3) 0.137(4) 1.000(3) 0.117(11) Uiso 1 1 d . . . H13 H 0.464(5) 0.2500 1.068(4) 0.110(15) Uiso 1 2 d S . . O1 O 0.5390(2) 0.2500 0.8895(2) 0.0933(9) Uani 1 2 d S . . S1 S 0.20999(6) 0.2500 0.44182(5) 0.0413(2) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0433(12) 0.0430(12) 0.0339(12) 0.000 0.0152(10) 0.000 C2 0.0511(15) 0.0793(19) 0.0417(14) 0.000 0.0229(12) 0.000 C3 0.0684(19) 0.105(3) 0.0342(14) 0.000 0.0238(13) 0.000 C4 0.0596(17) 0.090(2) 0.0303(13) 0.000 0.0088(13) 0.000 C5 0.0456(14) 0.0607(16) 0.0358(13) 0.000 0.0097(11) 0.000 C6 0.0406(11) 0.0354(11) 0.0309(11) 0.000 0.0102(9) 0.000 C7 0.0353(11) 0.0338(11) 0.0323(10) 0.000 0.0081(9) 0.000 C8 0.0358(11) 0.0342(11) 0.0315(11) 0.000 0.0068(9) 0.000 C9 0.0387(12) 0.0589(15) 0.0371(13) 0.000 0.0089(10) 0.000 C10 0.0310(12) 0.085(2) 0.0522(16) 0.000 0.0091(11) 0.000 C11 0.0368(13) 0.090(2) 0.0576(17) 0.000 0.0234(13) 0.000 C12 0.0497(14) 0.0713(17) 0.0481(15) 0.000 0.0268(13) 0.000 C13 0.0402(12) 0.0523(14) 0.0350(12) 0.000 0.0128(10) 0.000 C14 0.0368(11) 0.0351(11) 0.0341(11) 0.000 0.0118(9) 0.000 C15 0.0352(11) 0.0354(11) 0.0312(11) 0.000 0.0110(9) 0.000 C16 0.0352(11) 0.0344(11) 0.0323(11) 0.000 0.0123(9) 0.000 C17 0.0401(12) 0.0440(12) 0.0296(11) 0.000 0.0127(9) 0.000 C18 0.0391(12) 0.0652(16) 0.0346(12) 0.000 0.0094(10) 0.000 C19 0.0373(13) 0.0741(18) 0.0458(15) 0.000 0.0052(11) 0.000 C20 0.0550(17) 0.106(3) 0.0354(15) 0.000 0.0016(13) 0.000 O1 0.0347(10) 0.167(3) 0.0683(15) 0.000 0.0070(9) 0.000 S1 0.0335(3) 0.0564(4) 0.0343(3) 0.000 0.0125(2) 0.000 _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 1.387(3) . ? C1 C6 1.406(3) . ? C1 S1 1.752(2) . ? C2 C3 1.380(4) . ? C3 C4 1.383(5) . ? C4 C5 1.381(4) . ? C5 C6 1.407(3) . ? C6 C7 1.440(3) . ? C7 C16 1.398(3) . ? C7 C8 1.412(3) . ? C8 C9 1.387(3) . ? C8 C14 1.492(3) . ? C9 C10 1.389(4) . ? C10 C11 1.382(4) . ? C11 C12 1.376(4) . ? C12 C13 1.385(4) . ? C13 C14 1.387(3) . ? C14 C15 1.415(3) . ? C15 C16 1.416(3) . ? C15 C17 1.433(3) . ? C16 S1 1.724(2) . ? C17 C18 1.341(3) . ? C18 C19 1.461(3) . ? C19 O1 1.216(3) . ? C19 C20 1.497(5) . ? 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 122.3(2) . . ? C2 C1 S1 124.8(2) . . ? C6 C1 S1 112.89(17) . . ? C3 C2 C1 118.1(3) . . ? C2 C3 C4 121.1(3) . . ? C5 C4 C3 121.1(3) . . ? C4 C5 C6 119.5(3) . . ? C1 C6 C5 118.0(2) . . ? C1 C6 C7 110.67(19) . . ? C5 C6 C7 131.4(2) . . ? C16 C7 C8 108.1(2) . . ? C16 C7 C6 112.7(2) . . ? C8 C7 C6 139.3(2) . . ? C9 C8 C7 126.5(2) . . ? C9 C8 C14 127.3(2) . . ? C7 C8 C14 106.23(18) . . ? C8 C9 C10 129.2(2) . . ? C11 C10 C9 128.8(3) . . ? C12 C11 C10 129.5(3) . . ? C11 C12 C13 129.3(3) . . ? C12 C13 C14 129.4(2) . . ? C13 C14 C15 125.5(2) . . ? C13 C14 C8 126.5(2) . . ? C15 C14 C8 108.04(18) . . ? C14 C15 C16 106.25(18) . . ? C14 C15 C17 126.3(2) . . ? C16 C15 C17 127.5(2) . . ? C7 C16 C15 111.4(2) . . ? C7 C16 S1 112.96(17) . . ? C15 C16 S1 135.63(17) . . ? C18 C17 C15 126.5(2) . . ? C17 C18 C19 125.5(3) . . ? O1 C19 C18 120.0(3) . . ? O1 C19 C20 120.2(3) . . ? C18 C19 C20 119.8(2) . . ? C16 S1 C1 90.80(10) . . ? _diffrn_measured_fraction_theta_max 0.903 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.903 _refine_diff_density_max 0.313 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.043 data_azul-4a _database_code_depnum_ccdc_archive 'CCDC 232411' _audit_creation_method SHELXL-97 _chemical_name_systematic (E)-4-(11-azuleno[1,2-b]benzothiophenyl)-3-butene-2-one _chemical_name_common (E)-4-(11-azuleno(1,2-b)benzothiophenyl)-3-butene-2-one _chemical_melting_point 431 _chemical_formula_moiety 'benzothiophene, azulene, carbonyl' _chemical_formula_sum 'C20 H14 O S' _chemical_formula_weight 302.3 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 orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 18.905(3) _cell_length_b 4.7718(7) _cell_length_c 33.799(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3049.0(8) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour ? _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.211 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK¥a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15383 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_sigmaI/netI 0.1119 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 27.28 _reflns_number_total 5720 _reflns_number_gt 2635 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1310P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _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 0.60(16) _refine_ls_number_reflns 5720 _refine_ls_number_parameters 392 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1765 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.2379 _refine_ls_wR_factor_gt 0.1934 _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_restrained_S_all 0.917 _refine_ls_shift/su_max 0.002 _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 C101 C 0.6851(4) -0.0746(16) 0.1568(2) 0.056(2) Uani 1 1 d . . . C102 C 0.6354(4) -0.2547(16) 0.1731(2) 0.061(2) Uani 1 1 d . . . H102 H 0.6296 -0.2691 0.2004 0.073 Uiso 1 1 calc R . . C103 C 0.5954(5) -0.4102(19) 0.1475(3) 0.074(2) Uani 1 1 d . . . H103 H 0.5610 -0.5299 0.1576 0.089 Uiso 1 1 calc R . . C104 C 0.6050(4) -0.3931(17) 0.1066(3) 0.074(3) Uani 1 1 d . . . H104 H 0.5779 -0.5055 0.0900 0.089 Uiso 1 1 calc R . . C105 C 0.6532(4) -0.215(2) 0.0907(2) 0.070(2) Uani 1 1 d . . . H105 H 0.6579 -0.2033 0.0634 0.084 Uiso 1 1 calc R . . C106 C 0.6964(4) -0.0468(15) 0.1153(3) 0.055(2) Uani 1 1 d . . . C107 C 0.7519(4) 0.1536(15) 0.1069(3) 0.055(2) Uani 1 1 d . . . C108 C 0.7884(4) 0.2781(17) 0.0746(2) 0.057(2) Uani 1 1 d . . . C109 C 0.8374(4) 0.4661(15) 0.0892(2) 0.0487(18) Uani 1 1 d . . . C110 C 0.8823(4) 0.6306(16) 0.0682(2) 0.055(2) Uani 1 1 d . . . H110 H 0.8794 0.6088 0.0409 0.066 Uiso 1 1 calc R . . C111 C 0.9324(4) 0.8282(18) 0.0808(3) 0.074(3) Uani 1 1 d . . . H111 H 0.9573 0.9207 0.0610 0.089 Uiso 1 1 calc R . . C112 C 0.9491(5) 0.9017(17) 0.1195(3) 0.076(2) Uani 1 1 d . . . H112 H 0.9844 1.0364 0.1222 0.091 Uiso 1 1 calc R . . C113 C 0.9209(5) 0.8035(19) 0.1543(3) 0.072(3) Uani 1 1 d . . . H113 H 0.9401 0.8824 0.1770 0.087 Uiso 1 1 calc R . . C114 C 0.8707(4) 0.6142(16) 0.1608(2) 0.056(2) Uani 1 1 d . . . H114 H 0.8602 0.5777 0.1872 0.067 Uiso 1 1 calc R . . C115 C 0.8319(4) 0.4641(16) 0.1330(2) 0.0498(17) Uani 1 1 d . . . C116 C 0.7798(3) 0.2667(16) 0.1418(2) 0.0501(19) Uani 1 1 d . . . C117 C 0.7759(5) 0.190(2) 0.0329(3) 0.100(4) Uani 1 1 d . . . H117 H 0.7312 0.1099 0.0307 0.120 Uiso 1 1 calc R . . C119 C 0.7703(11) 0.031(4) -0.0332(4) 0.148(7) Uani 1 1 d . . . C120 C 0.8134(11) 0.143(4) -0.0624(6) 0.212(9) Uani 1 1 d . . . H123 H 0.7947 0.0947 -0.0880 0.318 Uiso 1 1 calc R . . H122 H 0.8603 0.0674 -0.0598 0.318 Uiso 1 1 calc R . . H121 H 0.8150 0.3427 -0.0598 0.318 Uiso 1 1 calc R . . C201 C 0.5293(4) 0.4363(16) 0.2735(2) 0.057(2) Uani 1 1 d . . . C202 C 0.5801(4) 0.2544(18) 0.2591(2) 0.061(2) Uani 1 1 d . . . H202 H 0.5879 0.2405 0.2320 0.073 Uiso 1 1 calc R . . C203 C 0.6194(4) 0.0926(17) 0.2853(4) 0.072(2) Uani 1 1 d . . . H203 H 0.6539 -0.0266 0.2752 0.086 Uiso 1 1 calc R . . C204 C 0.6094(5) 0.1020(18) 0.3251(3) 0.076(2) Uani 1 1 d . . . H204 H 0.6356 -0.0134 0.3417 0.091 Uiso 1 1 calc R . . C205 C 0.5596(4) 0.2851(16) 0.3408(3) 0.060(2) Uani 1 1 d . . . H205 H 0.5537 0.2943 0.3680 0.072 Uiso 1 1 calc R . . C206 C 0.5190(4) 0.4520(15) 0.3169(2) 0.0498(19) Uani 1 1 d . . . C207 C 0.4648(4) 0.6604(14) 0.3246(2) 0.054(2) Uani 1 1 d . . . C208 C 0.4293(4) 0.7790(16) 0.3578(2) 0.059(2) Uani 1 1 d . . . C209 C 0.3777(4) 0.9743(17) 0.3413(2) 0.058(2) Uani 1 1 d . . . C210 C 0.3321(5) 1.1414(17) 0.3644(3) 0.068(2) Uani 1 1 d . . . H210 H 0.3353 1.1198 0.3917 0.082 Uiso 1 1 calc R . . C211 C 0.2841(5) 1.3300(19) 0.3512(3) 0.078(3) Uani 1 1 d . . . H211 H 0.2602 1.4251 0.3712 0.094 Uiso 1 1 calc R . . C212 C 0.2638(5) 1.4078(18) 0.3127(3) 0.074(2) Uani 1 1 d . . . H212 H 0.2277 1.5391 0.3106 0.089 Uiso 1 1 calc R . . C213 C 0.2923(4) 1.3085(18) 0.2777(3) 0.068(2) Uani 1 1 d . . . H213 H 0.2738 1.3871 0.2548 0.081 Uiso 1 1 calc R . . C214 C 0.3428(4) 1.1158(18) 0.2720(2) 0.064(2) Uani 1 1 d . . . H214 H 0.3525 1.0774 0.2456 0.077 Uiso 1 1 calc R . . C215 C 0.3823(4) 0.9659(16) 0.2983(2) 0.055(2) Uani 1 1 d . . . C216 C 0.4370(3) 0.7658(14) 0.2898(2) 0.0440(17) Uani 1 1 d . . . C217 C 0.4407(6) 0.729(2) 0.3984(3) 0.092(3) Uani 1 1 d . . . H217 H 0.4008 0.7681 0.4136 0.111 Uiso 1 1 calc R . . C218 C 0.4912(8) 0.646(4) 0.4189(3) 0.174(7) Uani 1 1 d . . . H218 H 0.5340 0.6037 0.4067 0.209 Uiso 1 1 calc R . . C219 C 0.4842(12) 0.611(4) 0.4654(4) 0.176(8) Uani 1 1 d . . . C220 C 0.4288(9) 0.638(5) 0.4914(5) 0.211(10) Uani 1 1 d . . . H223 H 0.4415 0.5568 0.5164 0.317 Uiso 1 1 calc R . . H221 H 0.3880 0.5445 0.4810 0.317 Uiso 1 1 calc R . . H222 H 0.4183 0.8336 0.4951 0.317 Uiso 1 1 calc R . . O2 O 0.5477(8) 0.592(3) 0.4752(3) 0.242(8) Uani 1 1 d . . . O1 O 0.7276(7) -0.101(4) -0.0433(3) 0.249(9) Uani 1 1 d . . . S1 S 0.74174(11) 0.1391(4) 0.18467(6) 0.0617(6) Uani 1 1 d . . . S2 S 0.47362(11) 0.6401(4) 0.24707(5) 0.0639(6) Uani 1 1 d . . . C118 C 0.8012(10) 0.188(4) 0.0044(5) 0.174(6) Uiso 1 1 d . . . H118 H 0.8437 0.2844 0.0017 0.208 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 C101 0.044(4) 0.057(5) 0.066(5) 0.000(4) 0.006(4) 0.022(4) C102 0.059(5) 0.054(5) 0.070(6) 0.009(4) 0.015(4) -0.001(4) C103 0.074(6) 0.059(5) 0.091(7) 0.023(5) 0.023(6) 0.004(5) C104 0.050(5) 0.056(5) 0.116(8) -0.025(5) 0.009(5) -0.008(4) C105 0.055(5) 0.089(6) 0.065(5) -0.021(5) -0.013(4) -0.004(5) C106 0.038(4) 0.042(4) 0.087(6) 0.007(4) 0.014(4) 0.010(4) C107 0.053(5) 0.053(5) 0.061(5) -0.004(4) 0.002(4) 0.028(4) C108 0.064(5) 0.061(5) 0.046(4) -0.004(4) 0.006(4) 0.025(4) C109 0.054(5) 0.036(4) 0.056(4) -0.002(4) 0.002(4) 0.010(4) C110 0.055(5) 0.050(5) 0.059(5) 0.008(4) 0.003(4) 0.017(5) C111 0.058(5) 0.058(5) 0.106(7) 0.016(5) 0.026(5) -0.002(5) C112 0.067(6) 0.055(5) 0.106(8) -0.009(5) -0.006(6) 0.006(4) C113 0.067(6) 0.068(6) 0.081(7) -0.015(5) -0.018(5) 0.015(5) C114 0.057(5) 0.037(4) 0.074(5) -0.003(4) 0.007(4) 0.012(4) C115 0.044(4) 0.052(4) 0.053(4) -0.002(3) -0.004(3) 0.013(4) C116 0.042(4) 0.055(5) 0.054(4) -0.004(4) -0.006(4) 0.014(4) C117 0.095(7) 0.139(9) 0.065(6) 0.045(6) 0.026(5) 0.049(7) C119 0.193(18) 0.206(17) 0.044(7) -0.046(8) -0.052(9) 0.067(14) C120 0.27(2) 0.223(19) 0.148(15) -0.019(15) -0.112(17) -0.053(17) C201 0.055(5) 0.042(4) 0.075(5) -0.004(4) -0.008(4) -0.014(4) C202 0.057(5) 0.066(5) 0.059(5) -0.016(4) 0.003(4) -0.010(5) C203 0.045(4) 0.049(5) 0.121(8) -0.014(5) 0.011(5) 0.005(4) C204 0.071(6) 0.058(5) 0.098(7) -0.001(5) -0.020(5) -0.007(5) C205 0.058(5) 0.046(5) 0.077(5) -0.005(4) -0.009(4) 0.012(4) C206 0.039(4) 0.046(4) 0.065(5) -0.003(4) -0.005(4) -0.012(4) C207 0.060(5) 0.040(4) 0.060(5) -0.007(4) -0.005(4) -0.012(4) C208 0.061(6) 0.053(5) 0.062(5) -0.002(4) 0.011(4) -0.012(4) C209 0.055(5) 0.052(5) 0.067(5) -0.002(4) 0.008(4) -0.017(4) C210 0.072(6) 0.056(5) 0.075(5) 0.000(4) 0.014(4) 0.014(5) C211 0.079(7) 0.066(6) 0.090(7) -0.012(6) 0.024(5) -0.013(5) C212 0.054(5) 0.064(6) 0.105(8) 0.003(5) 0.006(5) 0.001(4) C213 0.051(5) 0.056(5) 0.095(7) 0.019(5) 0.004(5) -0.001(5) C214 0.050(5) 0.070(6) 0.072(5) 0.001(5) -0.009(4) -0.021(5) C215 0.074(6) 0.045(4) 0.047(5) 0.001(3) -0.012(4) -0.016(4) C216 0.042(4) 0.040(4) 0.050(4) -0.007(4) 0.000(3) -0.012(4) C217 0.126(8) 0.099(7) 0.052(5) 0.024(5) -0.033(5) -0.039(6) C218 0.190(14) 0.29(2) 0.046(6) -0.027(8) -0.024(7) 0.052(14) C219 0.23(2) 0.232(18) 0.065(8) 0.002(9) -0.079(11) 0.086(15) C220 0.145(14) 0.35(3) 0.135(14) -0.061(16) -0.007(10) 0.026(15) O2 0.266(15) 0.38(2) 0.081(7) 0.014(9) -0.016(8) 0.151(15) O1 0.192(12) 0.49(3) 0.069(6) 0.020(9) -0.030(6) -0.123(14) S1 0.0694(14) 0.0647(13) 0.0509(10) 0.0039(11) 0.0017(10) 0.0035(11) S2 0.0741(14) 0.0642(14) 0.0535(11) -0.0041(11) 0.0037(10) -0.0074(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 C101 C102 1.388(10) . ? C101 C106 1.424(11) . ? C101 S1 1.753(8) . ? C102 C103 1.368(12) . ? C103 C104 1.399(13) . ? C104 C105 1.357(11) . ? C105 C106 1.415(11) . ? C106 C107 1.449(10) . ? C107 C116 1.401(10) . ? C107 C108 1.421(11) . ? C108 C109 1.380(11) . ? C108 C117 1.491(12) . ? C109 C110 1.355(10) . ? C109 C115 1.486(9) . ? C110 C111 1.403(11) . ? C111 C112 1.391(12) . ? C112 C113 1.372(12) . ? C113 C114 1.329(11) . ? C114 C115 1.389(10) . ? C115 C116 1.395(10) . ? C116 S1 1.727(8) . ? C117 C118 1.074(18) . ? C119 O1 1.08(2) . ? C119 C120 1.39(2) . ? C119 C118 1.59(2) . ? C201 C202 1.383(11) . ? C201 C206 1.481(11) . ? C201 S2 1.690(8) . ? C202 C203 1.390(12) . ? C203 C204 1.360(13) . ? C204 C205 1.389(11) . ? C205 C206 1.367(10) . ? C206 C207 1.452(10) . ? C207 C216 1.382(10) . ? C207 C208 1.425(11) . ? C208 C217 1.409(11) . ? C208 C209 1.460(11) . ? C209 C210 1.410(11) . ? C209 C215 1.457(10) . ? C210 C211 1.354(12) . ? C211 C212 1.406(13) . ? C212 C213 1.385(12) . ? C213 C214 1.338(11) . ? C214 C215 1.364(10) . ? C215 C216 1.436(10) . ? C216 S2 1.711(7) . ? C217 C218 1.246(15) . ? C218 C219 1.586(18) . ? C219 O2 1.25(2) . ? C219 C220 1.37(2) . ? 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 C102 C101 C106 123.4(7) . . ? C102 C101 S1 124.0(6) . . ? C106 C101 S1 112.6(6) . . ? C103 C102 C101 117.3(8) . . ? C102 C103 C104 121.5(8) . . ? C105 C104 C103 121.0(8) . . ? C104 C105 C106 120.7(8) . . ? C105 C106 C101 116.1(7) . . ? C105 C106 C107 132.6(8) . . ? C101 C106 C107 111.3(7) . . ? C116 C107 C108 107.7(7) . . ? C116 C107 C106 111.1(7) . . ? C108 C107 C106 141.2(8) . . ? C109 C108 C107 108.9(7) . . ? C109 C108 C117 128.9(8) . . ? C107 C108 C117 122.1(8) . . ? C110 C109 C108 127.6(7) . . ? C110 C109 C115 124.6(7) . . ? C108 C109 C115 107.7(7) . . ? C109 C110 C111 130.8(8) . . ? C112 C111 C110 127.5(8) . . ? C113 C112 C111 129.1(9) . . ? C114 C113 C112 130.7(8) . . ? C113 C114 C115 128.0(8) . . ? C114 C115 C116 125.2(7) . . ? C114 C115 C109 129.3(7) . . ? C116 C115 C109 105.4(6) . . ? C115 C116 C107 110.2(7) . . ? C115 C116 S1 135.3(6) . . ? C107 C116 S1 114.5(6) . . ? C118 C117 C108 141.1(15) . . ? O1 C119 C120 115.8(13) . . ? O1 C119 C118 144(2) . . ? C120 C119 C118 99.9(18) . . ? C202 C201 C206 118.2(7) . . ? C202 C201 S2 127.3(7) . . ? C206 C201 S2 114.4(6) . . ? C201 C202 C203 119.6(8) . . ? C204 C203 C202 122.5(8) . . ? C203 C204 C205 119.5(8) . . ? C206 C205 C204 121.4(8) . . ? C205 C206 C207 133.6(7) . . ? C205 C206 C201 118.7(7) . . ? C207 C206 C201 107.7(7) . . ? C216 C207 C208 110.2(7) . . ? C216 C207 C206 111.5(7) . . ? C208 C207 C206 138.1(7) . . ? C217 C208 C207 129.0(9) . . ? C217 C208 C209 125.5(8) . . ? C207 C208 C209 105.5(7) . . ? C210 C209 C215 127.2(8) . . ? C210 C209 C208 124.0(7) . . ? C215 C209 C208 108.8(7) . . ? C211 C210 C209 127.1(9) . . ? C210 C211 C212 131.5(9) . . ? C213 C212 C211 126.5(9) . . ? C214 C213 C212 129.4(9) . . ? C213 C214 C215 131.1(8) . . ? C214 C215 C216 127.8(7) . . ? C214 C215 C209 127.0(8) . . ? C216 C215 C209 105.1(7) . . ? C207 C216 C215 110.3(6) . . ? C207 C216 S2 115.9(6) . . ? C215 C216 S2 133.9(6) . . ? C218 C217 C208 135.4(12) . . ? C217 C218 C219 121.4(14) . . ? O2 C219 C220 124.7(13) . . ? O2 C219 C218 101.0(17) . . ? C220 C219 C218 133.4(15) . . ? C116 S1 C101 90.5(4) . . ? C201 S2 C216 90.4(4) . . ? C117 C118 C119 123.7(19) . . ? _diffrn_measured_fraction_theta_max 0.927 _diffrn_reflns_theta_full 27.28 _diffrn_measured_fraction_theta_full 0.927 _refine_diff_density_max 0.633 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.072