# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Yoshitane Imai' _publ_contact_author_email Y-IMAI@APCH.KINDAI.AC.JP _publ_section_title ; Conformational and color polymorphism of achiral 2-methyl-3-(2-naphthalenylthio)-1,4-naphthalenedione ; loop_ _publ_author_name 'Yoshitane Imai' 'Takunori Harada' 'Takafumi Kinuta' 'Reiko Kuroda' 'Yoshio Matsubara' 'Keiko Nagasaki' ; Y.Sasaki ; 'Tomohiro Sato' 'Nobuo Tajima' # Attachment 'N3IMAI89.CIF' data_imai89_1 _database_code_depnum_ccdc_archive 'CCDC 702857' #data_im7662b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 O2 S' _chemical_formula_weight 330.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cc 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 22.763(3) _cell_length_b 4.9872(5) _cell_length_c 13.6097(15) _cell_angle_alpha 90.00 _cell_angle_beta 95.969(2) _cell_angle_gamma 90.00 _cell_volume 1536.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2715 _cell_measurement_theta_min 1.80 _cell_measurement_theta_max 27.15 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8977 _exptl_absorpt_correction_T_max 0.9783 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6362 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.85 _reflns_number_total 3232 _reflns_number_gt 2712 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SAMRT' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. The whole molecule is disordered into two orientation. Because of this, it was necessary to restrain all the bond distances and angles to assume standard values. Also the planarity of the naphthyl ring was imposed for all four of them. ; _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^)+(0.0644P)^2^+0.9320P] 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 0.358(208) _refine_ls_number_reflns 3232 _refine_ls_number_parameters 200 _refine_ls_number_restraints 138 _refine_ls_R_factor_all 0.0561 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1192 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.077 _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 0.3765(3) 0.0794(13) 0.0253(5) 0.013(2) Uiso 0.50 1 d PD A 1 C2 C 0.4072(2) -0.1182(11) -0.0332(4) 0.0153(16) Uiso 0.50 1 d PD A 1 C3 C 0.3935(3) -0.1463(12) -0.1306(4) 0.0175(17) Uiso 0.50 1 d PD A 1 C4 C 0.3460(3) 0.0130(13) -0.1855(4) 0.0176(16) Uiso 0.50 1 d PD A 1 C5 C 0.2685(3) 0.3733(16) -0.1768(5) 0.0216(18) Uiso 0.50 1 d PD A 1 H5 H 0.2561 0.3509 -0.2451 0.026 Uiso 0.50 1 calc PR A 1 C6 C 0.2416(4) 0.5654(18) -0.1231(6) 0.024(2) Uiso 0.50 1 d PD A 1 H6 H 0.2114 0.6740 -0.1559 0.029 Uiso 0.50 1 calc PR A 1 C7 C 0.2574(4) 0.604(2) -0.0235(6) 0.035(3) Uiso 0.50 1 d PD A 1 H7 H 0.2387 0.7369 0.0123 0.042 Uiso 0.50 1 calc PR A 1 C8 C 0.3015(5) 0.442(2) 0.0227(8) 0.040(4) Uiso 0.50 1 d PD A 1 H8 H 0.3129 0.4647 0.0913 0.048 Uiso 0.50 1 calc PR A 1 C9 C 0.3300(4) 0.2441(19) -0.0295(6) 0.022(3) Uiso 0.50 1 d PD A 1 C10 C 0.3137(3) 0.2125(13) -0.1318(4) 0.0164(17) Uiso 0.50 1 d PD A 1 O1 O 0.3869(2) 0.0871(13) 0.1147(4) 0.0276(13) Uiso 0.50 1 d PD A 1 S2 S 0.45791(8) -0.3314(5) 0.03409(15) 0.0223(2) Uani 0.50 1 d PD A 1 C3M C 0.4228(3) -0.3326(13) -0.1979(5) 0.0180(17) Uiso 0.50 1 d PD A 1 H3M1 H 0.4635 -0.3677 -0.1698 0.027 Uiso 0.50 1 calc PR A 1 H3M2 H 0.4232 -0.2491 -0.2630 0.027 Uiso 0.50 1 calc PR A 1 H3M3 H 0.4009 -0.5018 -0.2046 0.027 Uiso 0.50 1 calc PR A 1 O4 O 0.3307(3) -0.0100(11) -0.2724(4) 0.0309(14) Uiso 0.50 1 d PD A 1 C11 C 0.5366(3) 0.0833(15) 0.0159(6) 0.025(2) Uiso 0.50 1 d PD A 1 H11 H 0.5224 0.0877 -0.0522 0.029 Uiso 0.50 1 calc PR A 1 C12 C 0.5133(2) -0.0962(11) 0.0779(5) 0.0154(17) Uiso 0.50 1 d PD A 1 C13 C 0.5323(3) -0.0876(17) 0.1803(5) 0.0205(17) Uiso 0.50 1 d PD A 1 H13 H 0.5132 -0.1951 0.2250 0.025 Uiso 0.50 1 calc PR A 1 C14 C 0.5782(3) 0.0760(15) 0.2145(5) 0.024(2) Uiso 0.50 1 d PD A 1 H14 H 0.5937 0.0626 0.2819 0.028 Uiso 0.50 1 calc PR A 1 C15 C 0.6488(4) 0.4464(18) 0.1844(6) 0.028(2) Uiso 0.50 1 d PD A 1 H15 H 0.6655 0.4542 0.2512 0.034 Uiso 0.50 1 calc PR A 1 C16 C 0.6683(4) 0.6149(19) 0.1135(6) 0.027(2) Uiso 0.50 1 d PD A 1 H16 H 0.6985 0.7406 0.1338 0.032 Uiso 0.50 1 calc PR A 1 C17 C 0.6458(4) 0.6102(17) 0.0128(6) 0.026(2) Uiso 0.50 1 d PD A 1 H17 H 0.6612 0.7274 -0.0331 0.031 Uiso 0.50 1 calc PR A 1 C18 C 0.6014(4) 0.4348(16) -0.0175(6) 0.019(3) Uiso 0.50 1 d PD A 1 H18 H 0.5845 0.4294 -0.0843 0.022 Uiso 0.50 1 calc PR A 1 C19 C 0.5819(3) 0.2625(14) 0.0542(5) 0.016(2) Uiso 0.50 1 d PD A 1 C20 C 0.6034(3) 0.2632(14) 0.1539(4) 0.0125(16) Uiso 0.50 1 d PD A 1 C21 C 0.5305(3) 0.0716(13) -0.0078(5) 0.016(2) Uiso 0.50 1 d PD B 2 C22 C 0.5012(2) -0.1236(12) 0.0526(5) 0.0214(19) Uiso 0.50 1 d PD B 2 C23 C 0.5151(3) -0.1447(13) 0.1515(4) 0.0184(17) Uiso 0.50 1 d PD B 2 C24 C 0.5616(3) 0.0297(15) 0.2016(5) 0.0194(18) Uiso 0.50 1 d PD B 2 C25 C 0.6368(4) 0.3854(18) 0.1882(6) 0.026(2) Uiso 0.50 1 d PD B 2 H25 H 0.6463 0.3621 0.2573 0.032 Uiso 0.50 1 calc PR B 2 C26 C 0.6675(4) 0.572(2) 0.1393(7) 0.031(2) Uiso 0.50 1 d PD B 2 H26 H 0.6991 0.6714 0.1727 0.037 Uiso 0.50 1 calc PR B 2 C27 C 0.6507(3) 0.6103(16) 0.0403(6) 0.019(2) Uiso 0.50 1 d PD B 2 H27 H 0.6692 0.7448 0.0049 0.022 Uiso 0.50 1 calc PR B 2 C28 C 0.6072(4) 0.4542(18) -0.0071(7) 0.022(3) Uiso 0.50 1 d PD B 2 H28 H 0.5974 0.4843 -0.0758 0.026 Uiso 0.50 1 calc PR B 2 C29 C 0.5754(3) 0.2496(15) 0.0381(5) 0.018(2) Uiso 0.50 1 d PD B 2 C30 C 0.5921(3) 0.2297(14) 0.1392(5) 0.0170(18) Uiso 0.50 1 d PD B 2 O21 O 0.5159(2) 0.0969(12) -0.0964(4) 0.0240(12) Uiso 0.50 1 d PD B 2 S22 S 0.44791(8) -0.3312(5) -0.01341(15) 0.0223(2) Uani 0.50 1 d PD B 2 C23M C 0.4840(4) -0.3354(17) 0.2139(6) 0.035(2) Uiso 0.50 1 d PD B 2 H23A H 0.4594 -0.4581 0.1711 0.053 Uiso 0.50 1 calc PR B 2 H23B H 0.4591 -0.2341 0.2552 0.053 Uiso 0.50 1 calc PR B 2 H23C H 0.5133 -0.4386 0.2562 0.053 Uiso 0.50 1 calc PR B 2 O24 O 0.5737(3) 0.0166(11) 0.2914(4) 0.0327(15) Uiso 0.50 1 d PD B 2 C31 C 0.3705(4) 0.0822(17) 0.0054(7) 0.021(3) Uiso 0.50 1 d PD B 2 H31 H 0.3835 0.0690 0.0739 0.025 Uiso 0.50 1 calc PR B 2 C32 C 0.3961(3) -0.0875(13) -0.0607(5) 0.0173(17) Uiso 0.50 1 d PD B 2 C33 C 0.3744(3) -0.0891(15) -0.1596(5) 0.0157(15) Uiso 0.50 1 d PD B 2 H33 H 0.3896 -0.2127 -0.2036 0.019 Uiso 0.50 1 calc PR B 2 C34 C 0.3310(3) 0.0879(14) -0.1938(5) 0.0132(14) Uiso 0.50 1 d PD B 2 H34 H 0.3175 0.0930 -0.2622 0.016 Uiso 0.50 1 calc PR B 2 C35 C 0.2615(3) 0.4493(15) -0.1625(5) 0.0125(14) Uiso 0.50 1 d PD B 2 H35 H 0.2478 0.4507 -0.2308 0.015 Uiso 0.50 1 calc PR B 2 C36 C 0.2384(3) 0.6238(16) -0.1012(5) 0.0163(17) Uiso 0.50 1 d PD B 2 H36 H 0.2084 0.7461 -0.1258 0.020 Uiso 0.50 1 calc PR B 2 C37 C 0.2597(3) 0.6214(15) 0.0011(6) 0.0130(17) Uiso 0.50 1 d PD B 2 H37 H 0.2434 0.7435 0.0446 0.016 Uiso 0.50 1 calc PR B 2 C38 C 0.3027(3) 0.4485(15) 0.0380(6) 0.0084(19) Uiso 0.50 1 d PD B 2 H38 H 0.3161 0.4497 0.1065 0.010 Uiso 0.50 1 calc PR B 2 C39 C 0.3267(4) 0.2703(17) -0.0254(6) 0.010(2) Uiso 0.50 1 d PD B 2 C40 C 0.3058(4) 0.2650(17) -0.1270(6) 0.022(2) Uiso 0.50 1 d PD B 2 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 S2 0.0227(4) 0.0159(2) 0.0278(5) 0.0019(13) 0.0003(4) -0.0014(7) S22 0.0227(4) 0.0159(2) 0.0278(5) 0.0019(13) 0.0003(4) -0.0014(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.216(6) . ? C1 C9 1.480(7) . ? C1 C2 1.486(6) . ? C2 C3 1.337(6) . ? C2 S2 1.755(6) . ? C3 C4 1.479(6) . ? C3 C3M 1.509(6) . ? C4 O4 1.203(6) . ? C4 C10 1.476(6) . ? C5 C6 1.386(7) . ? C5 C10 1.393(6) . ? C6 C7 1.379(7) . ? C7 C8 1.387(8) . ? C8 C9 1.411(7) . ? C9 C10 1.412(7) . ? S2 C12 1.779(6) . ? C11 C12 1.373(6) . ? C11 C19 1.422(7) . ? C12 C13 1.415(6) . ? C13 C14 1.369(7) . ? C14 C20 1.407(6) . ? C15 C16 1.386(6) . ? C15 C20 1.410(7) . ? C16 C17 1.412(7) . ? C17 C18 1.367(7) . ? C18 C19 1.407(7) . ? C19 C20 1.394(6) . ? C21 O21 1.223(7) . ? C21 C29 1.446(8) . ? C21 C22 1.477(7) . ? C22 C23 1.354(8) . ? C22 S22 1.767(7) . ? C23 C24 1.481(8) . ? C23 C23M 1.500(8) . ? C24 O24 1.226(7) . ? C24 C30 1.524(8) . ? C25 C26 1.378(9) . ? C25 C30 1.393(8) . ? C26 C27 1.375(9) . ? C27 C28 1.366(9) . ? C28 C29 1.427(10) . ? C29 C30 1.393(9) . ? S22 C32 1.768(6) . ? C31 C39 1.402(9) . ? C31 C32 1.404(8) . ? C32 C33 1.385(7) . ? C33 C34 1.370(7) . ? C34 C40 1.429(8) . ? C35 C36 1.351(7) . ? C35 C40 1.412(8) . ? C36 C37 1.426(8) . ? C37 C38 1.360(8) . ? C38 C39 1.390(10) . ? C39 C40 1.415(9) . ? 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 C9 122.8(6) . . ? O1 C1 C2 120.2(6) . . ? C9 C1 C2 116.8(6) . . ? C3 C2 C1 121.7(5) . . ? C3 C2 S2 121.8(4) . . ? C1 C2 S2 116.3(4) . . ? C2 C3 C4 121.9(5) . . ? C2 C3 C3M 126.4(5) . . ? C4 C3 C3M 111.7(5) . . ? O4 C4 C10 116.3(6) . . ? O4 C4 C3 124.5(6) . . ? C10 C4 C3 119.2(5) . . ? C6 C5 C10 120.8(6) . . ? C7 C6 C5 122.1(7) . . ? C6 C7 C8 117.8(8) . . ? C7 C8 C9 121.9(9) . . ? C8 C9 C10 119.1(7) . . ? C8 C9 C1 118.5(7) . . ? C10 C9 C1 122.4(6) . . ? C5 C10 C9 118.4(6) . . ? C5 C10 C4 123.6(6) . . ? C9 C10 C4 118.0(6) . . ? C2 S2 C12 100.4(3) . . ? C12 C11 C19 119.7(7) . . ? C11 C12 C13 119.2(6) . . ? C11 C12 S2 121.9(5) . . ? C13 C12 S2 118.8(5) . . ? C14 C13 C12 119.8(6) . . ? C13 C14 C20 122.6(7) . . ? C16 C15 C20 117.8(7) . . ? C15 C16 C17 123.7(7) . . ? C18 C17 C16 119.1(8) . . ? C17 C18 C19 117.3(7) . . ? C20 C19 C18 124.7(6) . . ? C20 C19 C11 121.8(6) . . ? C18 C19 C11 113.6(6) . . ? C19 C20 C14 116.5(6) . . ? C19 C20 C15 117.4(6) . . ? C14 C20 C15 126.1(6) . . ? O21 C21 C29 118.0(6) . . ? O21 C21 C22 121.6(6) . . ? C29 C21 C22 120.3(6) . . ? C23 C22 C21 122.1(6) . . ? C23 C22 S22 122.5(5) . . ? C21 C22 S22 115.4(5) . . ? C22 C23 C24 119.6(6) . . ? C22 C23 C23M 122.5(6) . . ? C24 C23 C23M 117.9(6) . . ? O24 C24 C23 120.3(6) . . ? O24 C24 C30 121.5(7) . . ? C23 C24 C30 118.2(6) . . ? C26 C25 C30 121.8(8) . . ? C27 C26 C25 117.6(8) . . ? C28 C27 C26 119.9(8) . . ? C27 C28 C29 125.4(8) . . ? C30 C29 C28 112.2(7) . . ? C30 C29 C21 119.4(6) . . ? C28 C29 C21 128.4(7) . . ? C29 C30 C25 123.0(7) . . ? C29 C30 C24 120.3(6) . . ? C25 C30 C24 116.8(6) . . ? C32 S22 C22 100.3(3) . . ? C39 C31 C32 122.8(8) . . ? C33 C32 C31 119.8(6) . . ? C33 C32 S22 120.5(5) . . ? C31 C32 S22 119.1(5) . . ? C34 C33 C32 119.9(6) . . ? C33 C34 C40 120.3(6) . . ? C36 C35 C40 121.3(6) . . ? C35 C36 C37 118.9(6) . . ? C38 C37 C36 121.6(7) . . ? C37 C38 C39 119.4(8) . . ? C38 C39 C31 123.8(7) . . ? C38 C39 C40 120.3(7) . . ? C31 C39 C40 115.8(8) . . ? C35 C40 C39 118.5(6) . . ? C35 C40 C34 120.2(6) . . ? C39 C40 C34 121.2(7) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.402 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.052 #===END data_imai89_2 _database_code_depnum_ccdc_archive 'CCDC 702858' #data_im8788a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H14 O2 S' _chemical_formula_weight 330.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.0141(17) _cell_length_b 5.8339(12) _cell_length_c 16.979(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.228(3) _cell_angle_gamma 90.00 _cell_volume 787.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 3201 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.88 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 344 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8908 _exptl_absorpt_correction_T_max 0.9893 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6936 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 27.88 _reflns_number_total 3513 _reflns_number_gt 3201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0504P)^2^+0.0617P] 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 0.13(7) _refine_ls_number_reflns 3513 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0968 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.002 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 0.7771(3) 0.4840(4) 0.79674(12) 0.0217(4) Uani 1 1 d . . . C2 C 0.6137(3) 0.3569(4) 0.78323(12) 0.0195(4) Uani 1 1 d . . . C3 C 0.4786(3) 0.4174(4) 0.81792(12) 0.0213(5) Uani 1 1 d . . . C4 C 0.4849(2) 0.6280(4) 0.86794(11) 0.0220(4) Uani 1 1 d . . . C5 C 0.6585(3) 0.9346(4) 0.93907(13) 0.0261(5) Uani 1 1 d . . . H5 H 0.5627 0.9810 0.9628 0.031 Uiso 1 1 calc R . . C6 C 0.8082(3) 1.0530(4) 0.95561(13) 0.0299(5) Uani 1 1 d . . . H6 H 0.8158 1.1796 0.9911 0.036 Uiso 1 1 calc R . . C7 C 0.9475(3) 0.9859(4) 0.92019(13) 0.0295(5) Uani 1 1 d . . . H7 H 1.0502 1.0681 0.9311 0.035 Uiso 1 1 calc R . . C8 C 0.9379(3) 0.8010(4) 0.86928(13) 0.0251(5) Uani 1 1 d . . . H8 H 1.0340 0.7566 0.8454 0.030 Uiso 1 1 calc R . . C9 C 0.7890(3) 0.6795(4) 0.85268(12) 0.0209(4) Uani 1 1 d . . . C10 C 0.6478(3) 0.7480(4) 0.88789(12) 0.0217(4) Uani 1 1 d . . . C3M C 0.3161(3) 0.2883(4) 0.80960(14) 0.0280(5) Uani 1 1 d . . . H3M1 H 0.3017 0.2064 0.7588 0.042 Uiso 1 1 calc R . . H3M2 H 0.2228 0.3958 0.8114 0.042 Uiso 1 1 calc R . . H3M3 H 0.3175 0.1779 0.8532 0.042 Uiso 1 1 calc R . . O1 O 0.89780(19) 0.4252(3) 0.76490(9) 0.0303(4) Uani 1 1 d . . . O4 O 0.35742(19) 0.7028(3) 0.89140(9) 0.0306(4) Uani 1 1 d . . . S S 0.61082(6) 0.10246(8) 0.72678(3) 0.02238(13) Uani 1 1 d . . . C11 C 0.7519(2) 0.0438(3) 0.59229(12) 0.0182(4) Uani 1 1 d . . . H11 H 0.7919 -0.0963 0.6162 0.022 Uiso 1 1 calc R . . C12 C 0.6667(2) 0.1954(4) 0.63427(11) 0.0178(4) Uani 1 1 d . . . C13 C 0.6089(2) 0.4068(3) 0.60017(12) 0.0179(4) Uani 1 1 d . . . H13 H 0.5492 0.5105 0.6295 0.021 Uiso 1 1 calc R . . C14 C 0.6389(2) 0.4612(3) 0.52535(11) 0.0170(4) Uani 1 1 d . . . H14 H 0.6019 0.6049 0.5033 0.020 Uiso 1 1 calc R . . C15 C 0.7539(2) 0.3590(4) 0.40111(12) 0.0211(5) Uani 1 1 d . . . H15 H 0.7163 0.5009 0.3778 0.025 Uiso 1 1 calc R . . C16 C 0.8361(2) 0.2062(4) 0.35848(12) 0.0220(4) Uani 1 1 d . . . H16 H 0.8551 0.2426 0.3058 0.026 Uiso 1 1 calc R . . C17 C 0.8931(3) -0.0057(4) 0.39243(12) 0.0214(4) Uani 1 1 d . . . H17 H 0.9508 -0.1105 0.3626 0.026 Uiso 1 1 calc R . . C18 C 0.8653(2) -0.0597(3) 0.46780(12) 0.0190(4) Uani 1 1 d . . . H18 H 0.9032 -0.2029 0.4899 0.023 Uiso 1 1 calc R . . C19 C 0.7807(2) 0.0945(4) 0.51355(11) 0.0166(4) Uani 1 1 d . . . C20 C 0.7244(2) 0.3075(3) 0.47948(12) 0.0166(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 0.0178(10) 0.0292(12) 0.0182(10) 0.0050(9) 0.0027(8) 0.0000(9) C2 0.0208(10) 0.0239(11) 0.0135(10) 0.0019(8) 0.0010(8) 0.0006(8) C3 0.0173(10) 0.0273(11) 0.0183(10) 0.0058(9) -0.0010(8) 0.0019(8) C4 0.0206(10) 0.0295(12) 0.0162(9) 0.0051(9) 0.0035(7) 0.0024(9) C5 0.0258(12) 0.0318(12) 0.0207(11) -0.0003(9) 0.0026(9) 0.0031(9) C6 0.0313(12) 0.0331(14) 0.0242(11) -0.0039(10) -0.0009(9) 0.0004(10) C7 0.0247(12) 0.0331(13) 0.0289(12) 0.0018(10) -0.0041(9) -0.0072(10) C8 0.0203(11) 0.0323(12) 0.0227(12) 0.0035(9) 0.0022(8) 0.0008(9) C9 0.0189(10) 0.0283(11) 0.0150(10) 0.0046(8) -0.0002(7) 0.0018(8) C10 0.0203(10) 0.0292(11) 0.0155(10) 0.0054(9) 0.0025(8) 0.0014(9) C3M 0.0210(11) 0.0335(12) 0.0301(13) 0.0023(10) 0.0062(9) -0.0011(10) O1 0.0181(8) 0.0464(11) 0.0273(9) -0.0061(7) 0.0064(6) 0.0012(7) O4 0.0216(8) 0.0397(9) 0.0328(9) -0.0025(8) 0.0125(6) 0.0026(7) S 0.0258(3) 0.0217(2) 0.0202(2) 0.0029(2) 0.00491(18) -0.0004(2) C11 0.0159(9) 0.0154(10) 0.0222(10) 0.0025(7) -0.0012(7) 0.0012(7) C12 0.0135(9) 0.0221(10) 0.0176(9) 0.0020(8) 0.0012(7) -0.0024(8) C13 0.0148(10) 0.0174(10) 0.0214(11) -0.0029(8) 0.0019(8) 0.0007(8) C14 0.0138(9) 0.0135(9) 0.0228(10) 0.0017(8) -0.0008(7) 0.0010(8) C15 0.0188(11) 0.0197(10) 0.0240(11) 0.0013(9) -0.0005(8) -0.0008(8) C16 0.0216(11) 0.0259(11) 0.0190(10) -0.0005(9) 0.0052(8) -0.0021(9) C17 0.0166(10) 0.0229(11) 0.0258(11) -0.0072(9) 0.0077(8) 0.0006(8) C18 0.0147(10) 0.0150(9) 0.0270(11) -0.0022(8) 0.0013(8) -0.0006(8) C19 0.0119(8) 0.0153(8) 0.0220(9) -0.0003(9) 0.0000(7) -0.0027(8) C20 0.0118(9) 0.0164(9) 0.0209(10) -0.0003(8) -0.0003(7) -0.0013(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.216(2) . ? C1 C9 1.479(3) . ? C1 C2 1.497(3) . ? C2 C3 1.343(3) . ? C2 S 1.765(2) . ? C3 C4 1.491(3) . ? C3 C3M 1.496(3) . ? C4 O4 1.223(2) . ? C4 C10 1.482(3) . ? C5 C6 1.382(3) . ? C5 C10 1.389(3) . ? C6 C7 1.389(3) . ? C7 C8 1.378(3) . ? C8 C9 1.386(3) . ? C9 C10 1.403(3) . ? S C12 1.772(2) . ? C11 C12 1.371(3) . ? C11 C19 1.416(3) . ? C12 C13 1.416(3) . ? C13 C14 1.360(3) . ? C14 C20 1.419(3) . ? C15 C16 1.369(3) . ? C15 C20 1.413(3) . ? C16 C17 1.415(3) . ? C17 C18 1.363(3) . ? C18 C19 1.416(3) . ? C19 C20 1.420(3) . ? 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 C9 120.82(19) . . ? O1 C1 C2 121.4(2) . . ? C9 C1 C2 117.72(18) . . ? C3 C2 C1 122.7(2) . . ? C3 C2 S 120.19(17) . . ? C1 C2 S 116.84(15) . . ? C2 C3 C4 119.69(19) . . ? C2 C3 C3M 124.5(2) . . ? C4 C3 C3M 115.82(18) . . ? O4 C4 C10 120.3(2) . . ? O4 C4 C3 120.67(19) . . ? C10 C4 C3 118.99(17) . . ? C6 C5 C10 120.2(2) . . ? C5 C6 C7 119.7(2) . . ? C8 C7 C6 120.5(2) . . ? C7 C8 C9 120.4(2) . . ? C8 C9 C10 119.2(2) . . ? C8 C9 C1 120.62(19) . . ? C10 C9 C1 120.16(19) . . ? C5 C10 C9 120.0(2) . . ? C5 C10 C4 119.76(19) . . ? C9 C10 C4 120.19(19) . . ? C2 S C12 103.69(10) . . ? C12 C11 C19 120.46(19) . . ? C11 C12 C13 120.56(18) . . ? C11 C12 S 117.50(16) . . ? C13 C12 S 121.52(16) . . ? C14 C13 C12 119.88(19) . . ? C13 C14 C20 121.29(18) . . ? C16 C15 C20 120.6(2) . . ? C15 C16 C17 120.37(19) . . ? C18 C17 C16 120.13(19) . . ? C17 C18 C19 120.95(19) . . ? C11 C19 C18 122.09(19) . . ? C11 C19 C20 119.09(18) . . ? C18 C19 C20 118.81(18) . . ? C15 C20 C14 122.14(18) . . ? C15 C20 C19 119.17(18) . . ? C14 C20 C19 118.69(18) . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.366 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.052