# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Prof Tayur Guru Row' _publ_contact_author_email SSCTNG@SSCU.IISC.ERNET.IN _publ_section_title ; Evaluation of Intermolecular interactions in thioisocoumarin derivatives: The role of sulphur atom in generating packing motifs ; loop_ _publ_author_name 'T.N. Guru Row' 'Venkatesha R. Hathwar' 'F. Nawaz Khan' 'P. Manivel' # Attachment 'TI-1.cif' data_chsic_m _database_code_depnum_ccdc_archive 'CCDC 656918' #============================================================================== _audit_creation_date 'Aug 08 00:02:31 2008' _audit_creation_method ' SHELXL-97' _audit_update_record ; ; _chemical_name_systematic ; ; _chemical_name_common 3-Cyclohexyl-1H-isochromene-1-thione _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 O S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H16 O S' _chemical_formula_iupac ? _chemical_formula_weight 244.35 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 8.9463(14) _cell_length_b 12.335(2) _cell_length_c 12.338(2) _cell_angle_alpha 90 _cell_angle_beta 105.704(3) _cell_angle_gamma 90 _cell_volume 1310.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 1537 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 25.32 _cell_special_details ; ? ; _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.16 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.228 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North, Phillips & Mathews, 1968)' _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9161 _exptl_absorpt_correction_T_max 0.9644 #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 10010 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0378 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; _reflns_number_total 2570 _reflns_number_gt 1640 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== _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^)+(0.0515P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2570 _refine_ls_number_parameters 218 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0785 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1173 _refine_ls_wR_factor_gt 0.1055 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.124 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.032 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.01784(8) 0.53284(6) 0.29523(6) 0.0873(3) Uani 1 1 d . . . O1 O 0.15208(15) 0.40566(11) 0.18893(10) 0.0591(4) Uani 1 1 d . . . C1 C 0.1084(2) 0.50996(17) 0.19872(18) 0.0601(6) Uani 1 1 d . . . C2 C 0.2237(2) 0.37076(16) 0.10901(15) 0.0508(5) Uani 1 1 d . . . C3 C 0.2524(2) 0.44076(18) 0.03538(17) 0.0596(6) Uani 1 1 d D . . C4 C 0.2485(3) 0.6294(2) -0.0352(2) 0.0827(8) Uani 1 1 d D . . C5 C 0.2159(4) 0.7367(3) -0.0249(3) 0.1026(10) Uani 1 1 d D . . C6 C 0.1482(4) 0.7714(2) 0.0574(3) 0.1024(10) Uani 1 1 d D . . C7 C 0.1123(3) 0.6991(2) 0.1312(3) 0.0827(7) Uani 1 1 d D . . C8 C 0.1454(2) 0.58805(17) 0.12258(17) 0.0619(6) Uani 1 1 d . . . C9 C 0.2153(2) 0.55305(18) 0.03960(18) 0.0629(6) Uani 1 1 d . . . C10 C 0.2603(2) 0.25314(15) 0.12480(14) 0.0500(5) Uani 1 1 d D . . C11 C 0.3846(3) 0.23255(19) 0.23504(16) 0.0656(6) Uani 1 1 d D . . C12 C 0.4129(3) 0.1122(2) 0.25559(19) 0.0727(7) Uani 1 1 d D . . C13 C 0.4587(3) 0.0590(2) 0.1584(2) 0.0809(7) Uani 1 1 d D . . C14 C 0.3363(3) 0.0800(2) 0.0484(2) 0.0789(7) Uani 1 1 d D . . C15 C 0.3072(3) 0.20096(18) 0.02750(17) 0.0625(6) Uani 1 1 d D . . H3 H 0.303(2) 0.4143(15) -0.0239(14) 0.064(6) Uiso 1 1 d D . . H4 H 0.297(3) 0.6032(19) -0.0978(17) 0.099(8) Uiso 1 1 d D . . H5 H 0.241(3) 0.7948(19) -0.079(2) 0.125(9) Uiso 1 1 d D . . H6 H 0.119(3) 0.8511(16) 0.063(2) 0.143(11) Uiso 1 1 d D . . H7 H 0.066(2) 0.7201(18) 0.1944(16) 0.087(8) Uiso 1 1 d D . . H10 H 0.1578(19) 0.2157(14) 0.1292(14) 0.065(5) Uiso 1 1 d D . . H11A H 0.489(2) 0.2720(18) 0.2288(19) 0.096(8) Uiso 1 1 d D . . H11B H 0.353(2) 0.2727(16) 0.2986(16) 0.088(7) Uiso 1 1 d D . . H12A H 0.497(2) 0.097(2) 0.3315(16) 0.105(8) Uiso 1 1 d D . . H12B H 0.309(2) 0.0744(16) 0.2628(17) 0.082(7) Uiso 1 1 d D . . H13A H 0.475(3) -0.0233(14) 0.172(2) 0.100(8) Uiso 1 1 d D . . H13B H 0.567(2) 0.0950(18) 0.1561(19) 0.097(8) Uiso 1 1 d D . . H14A H 0.230(2) 0.042(2) 0.048(2) 0.128(11) Uiso 1 1 d D . . H14B H 0.372(2) 0.0513(17) -0.0201(16) 0.090(7) Uiso 1 1 d D . . H15A H 0.4067(19) 0.2407(14) 0.0233(15) 0.064(6) Uiso 1 1 d D . . H15B H 0.2237(19) 0.2171(15) -0.0468(14) 0.071(6) Uiso 1 1 d 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 S1 0.0839(5) 0.0862(5) 0.0985(5) -0.0252(3) 0.0364(4) 0.0111(3) O1 0.0618(9) 0.0557(9) 0.0633(8) -0.0042(6) 0.0229(7) 0.0055(7) C1 0.0453(12) 0.0559(13) 0.0712(13) -0.0151(10) 0.0023(10) 0.0054(10) C2 0.0469(11) 0.0581(13) 0.0471(10) -0.0035(9) 0.0122(9) 0.0017(9) C3 0.0574(13) 0.0644(15) 0.0545(12) 0.0025(10) 0.0108(10) 0.0017(10) C4 0.0778(17) 0.0735(19) 0.0873(18) 0.0238(14) 0.0060(14) -0.0013(13) C5 0.088(2) 0.079(2) 0.123(3) 0.0357(19) -0.0005(19) -0.0072(16) C6 0.087(2) 0.060(2) 0.139(3) 0.0139(19) -0.0074(19) 0.0035(15) C7 0.0691(16) 0.0603(18) 0.104(2) -0.0044(14) -0.0029(14) 0.0054(13) C8 0.0465(12) 0.0527(14) 0.0737(14) -0.0010(11) -0.0058(10) 0.0010(10) C9 0.0544(13) 0.0583(15) 0.0656(13) 0.0072(10) -0.0012(10) -0.0024(10) C10 0.0482(12) 0.0541(13) 0.0491(11) -0.0020(8) 0.0158(9) 0.0042(9) C11 0.0675(15) 0.0788(17) 0.0472(11) -0.0033(10) 0.0102(11) 0.0147(12) C12 0.0701(16) 0.0814(18) 0.0648(14) 0.0166(12) 0.0155(12) 0.0227(13) C13 0.0790(18) 0.0736(18) 0.0892(18) 0.0056(13) 0.0211(14) 0.0276(14) C14 0.092(2) 0.0701(17) 0.0745(16) -0.0154(12) 0.0226(14) 0.0209(14) C15 0.0670(15) 0.0702(15) 0.0505(12) -0.0043(10) 0.0163(11) 0.0099(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.636(2) . ? O1 C1 1.359(2) . ? O1 C2 1.382(2) . ? C1 C8 1.445(3) . ? C2 C3 1.328(3) . ? C2 C10 1.489(3) . ? C3 C9 1.429(3) . ? C3 H3 1.014(14) . ? C4 C5 1.369(4) . ? C4 C9 1.405(3) . ? C4 H4 1.036(16) . ? C5 C6 1.384(4) . ? C5 H5 1.042(17) . ? C6 C7 1.373(4) . ? C6 H6 1.024(18) . ? C7 C8 1.411(3) . ? C7 H7 1.013(15) . ? C8 C9 1.404(3) . ? C10 C15 1.518(2) . ? C10 C11 1.527(3) . ? C10 H10 1.041(14) . ? C11 C12 1.516(3) . ? C11 H11A 1.077(16) . ? C11 H11B 1.028(15) . ? C12 C13 1.518(3) . ? C12 H12A 1.045(16) . ? C12 H12B 1.065(16) . ? C13 C14 1.518(3) . ? C13 H13A 1.033(16) . ? C13 H13B 1.075(16) . ? C14 C15 1.524(3) . ? C14 H14A 1.063(17) . ? C14 H14B 1.045(16) . ? C15 H15A 1.030(14) . ? C15 H15B 1.033(15) . ? 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 C8 116.84(18) . . ? O1 C1 S1 116.02(16) . . ? O1 C2 C10 109.77(15) . . ? C1 O1 C2 123.92(16) . . ? C2 C3 C9 121.0(2) . . ? C2 C10 C15 114.07(16) . . ? C2 C10 C11 111.09(16) . . ? C2 C10 H10 105.9(10) . . ? C2 C3 H3 119.5(11) . . ? C3 C2 O1 119.91(19) . . ? C3 C2 C10 130.30(18) . . ? C4 C5 C6 120.9(3) . . ? C4 C9 C3 122.2(2) . . ? C4 C5 H5 121.2(16) . . ? C5 C4 C9 120.0(3) . . ? C5 C4 H4 120.9(14) . . ? C5 C6 H6 121.3(17) . . ? C6 C7 C8 119.3(3) . . ? C6 C7 H7 124.2(13) . . ? C6 C5 H5 117.9(16) . . ? C7 C6 C5 120.8(3) . . ? C7 C6 H6 117.8(17) . . ? C7 C8 C1 120.6(2) . . ? C8 C9 C4 119.2(2) . . ? C8 C9 C3 118.6(2) . . ? C8 C1 S1 127.14(17) . . ? C8 C7 H7 116.4(13) . . ? C9 C8 C7 119.8(2) . . ? C9 C3 H3 119.5(11) . . ? C9 C4 H4 119.1(14) . . ? C9 C8 C1 119.63(19) . . ? C10 C11 H11A 107.4(12) . . ? C10 C11 H11B 108.4(12) . . ? C10 C15 H15B 109.4(10) . . ? C10 C15 C14 110.63(18) . . ? C10 C15 H15A 105.4(10) . . ? C11 C12 C13 111.1(2) . . ? C11 C10 H10 108.6(10) . . ? C11 C12 H12A 111.7(14) . . ? C11 C12 H12B 109.5(11) . . ? C12 C11 C10 111.11(18) . . ? C12 C11 H11A 110.2(13) . . ? C12 C11 H11B 114.3(12) . . ? C12 C13 H13A 110.5(14) . . ? C12 C13 H13B 106.3(13) . . ? C13 C14 C15 111.6(2) . . ? C13 C14 H14A 110.8(16) . . ? C13 C14 H14B 111.0(12) . . ? C13 C12 H12A 110.5(13) . . ? C13 C12 H12B 107.7(12) . . ? C14 C13 C12 110.4(2) . . ? C14 C13 H13A 110.5(14) . . ? C14 C15 H15A 111.4(10) . . ? C14 C13 H13B 110.1(13) . . ? C14 C15 H15B 112.9(11) . . ? C15 C14 H14B 105.7(12) . . ? C15 C10 H10 106.8(10) . . ? C15 C14 H14A 108.7(16) . . ? C15 C10 C11 110.06(16) . . ? H11A C11 H11B 105.0(17) . . ? H12A C12 H12B 106.1(18) . . ? H13A C13 H13B 108.8(19) . . ? H14A C14 H14B 109(2) . . ? H15A C15 H15B 106.9(15) . . ? 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 S1 C1 C8 C7 4.3(3) . . . . ? S1 C1 C8 C9 -175.91(15) . . . . ? O1 C1 C8 C9 3.4(3) . . . . ? O1 C1 C8 C7 -176.33(17) . . . . ? O1 C2 C10 C15 167.60(16) . . . . ? O1 C2 C10 C11 -67.3(2) . . . . ? O1 C2 C3 C9 2.2(3) . . . . ? C1 O1 C2 C3 -0.5(3) . . . . ? C1 O1 C2 C10 177.99(15) . . . . ? C1 C8 C9 C4 179.01(18) . . . . ? C1 C8 C9 C3 -2.0(3) . . . . ? C2 C3 C9 C8 -0.9(3) . . . . ? C2 C3 C9 C4 178.1(2) . . . . ? C2 C10 C11 C12 175.57(18) . . . . ? C2 O1 C1 C8 -2.3(2) . . . . ? C2 C10 C15 C14 -177.77(18) . . . . ? C2 O1 C1 S1 177.16(13) . . . . ? C3 C2 C10 C15 -14.1(3) . . . . ? C3 C2 C10 C11 111.0(2) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C5 C4 C9 C8 1.5(3) . . . . ? C5 C4 C9 C3 -177.6(2) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C6 C7 C8 C9 0.5(3) . . . . ? C6 C7 C8 C1 -179.8(2) . . . . ? C7 C8 C9 C4 -1.2(3) . . . . ? C7 C8 C9 C3 177.81(18) . . . . ? C9 C4 C5 C6 -0.9(4) . . . . ? C10 C2 C3 C9 -176.01(18) . . . . ? C10 C11 C12 C13 57.0(3) . . . . ? C11 C10 C15 C14 56.6(2) . . . . ? C11 C12 C13 C14 -55.9(3) . . . . ? C12 C13 C14 C15 55.9(3) . . . . ? C13 C14 C15 C10 -56.8(3) . . . . ? C15 C10 C11 C12 -57.1(2) . . . . ? #===END # Attachment 'TI-2.cif' data_ti2_m _database_code_depnum_ccdc_archive 'CCDC 656920' #============================================================================== _audit_creation_date 'Aug 07 22:13:43 2008' _audit_creation_method ' SHELXL-97' _audit_update_record ; ; #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common 3-p-tolyl-1H-isochromene-1-thione _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 O S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H12 O S' _chemical_formula_iupac ? _chemical_formula_weight 252.33 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 7.4622(8) _cell_length_b 12.2143(12) _cell_length_c 14.4832(15) _cell_angle_alpha 81.027(2) _cell_angle_beta 83.319(2) _cell_angle_gamma 85.407(2) _cell_volume 1292.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 3144 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.19 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.09 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.234 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9328 _exptl_absorpt_correction_T_max 0.9792 #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 12910 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 4778 # number of observed reflections (> n sig(I)) _reflns_number_gt 3274 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2004)' _computing_cell_refinement 'SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT ' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' #=============================================================================== _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^)+(0.0584P)^2^+0.2471P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4778 _refine_ls_number_parameters 421 _refine_ls_number_restraints 30 _refine_ls_R_factor_all 0.0880 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1251 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.317 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.045 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.23940(11) 0.31934(6) 0.65293(6) 0.0716(3) Uani 1 1 d . . . O1 O 0.2383(2) 0.14692(14) 0.57328(12) 0.0580(5) Uani 1 1 d . . . C1 C 0.2287(3) 0.1849(2) 0.65745(19) 0.0539(7) Uani 1 1 d . . . C2 C 0.2379(3) 0.0364(2) 0.56318(19) 0.0528(6) Uani 1 1 d . . . C3 C 0.2250(4) -0.0401(2) 0.6395(2) 0.0620(7) Uani 1 1 d D . . C4 C 0.1973(5) -0.0888(3) 0.8131(2) 0.0780(9) Uani 1 1 d D . . C5 C 0.1877(5) -0.0567(3) 0.8998(2) 0.0871(10) Uani 1 1 d D . . C6 C 0.1871(5) 0.0544(3) 0.9088(2) 0.0794(9) Uani 1 1 d D . . C7 C 0.1972(4) 0.1335(3) 0.8306(2) 0.0679(8) Uani 1 1 d D . . C8 C 0.2105(3) 0.1027(2) 0.74084(19) 0.0536(6) Uani 1 1 d . . . C9 C 0.2109(4) -0.0099(2) 0.73136(19) 0.0580(7) Uani 1 1 d . . . C10 C 0.2537(3) 0.0215(2) 0.46444(18) 0.0534(6) Uani 1 1 d . . . C11 C 0.2582(5) 0.1105(3) 0.3932(2) 0.0768(9) Uani 1 1 d D . . C12 C 0.2733(5) 0.0941(3) 0.3003(2) 0.0848(10) Uani 1 1 d D . . C13 C 0.2841(4) -0.0100(3) 0.2748(2) 0.0640(7) Uani 1 1 d . . . C14 C 0.2792(5) -0.0972(3) 0.3461(2) 0.0872(10) Uani 1 1 d D . . C15 C 0.2631(5) -0.0825(3) 0.4392(2) 0.0860(11) Uani 1 1 d D . . C16 C 0.2994(5) -0.0272(4) 0.1728(2) 0.0850(10) Uani 1 1 d D . . S1' S 0.22202(9) 0.29468(7) 0.05847(5) 0.0689(3) Uani 1 1 d . . . O1' O 0.4872(2) 0.34528(14) 0.13623(11) 0.0502(4) Uani 1 1 d . . . C1' C 0.4280(3) 0.3346(2) 0.05299(17) 0.0476(6) Uani 1 1 d . . . C2' C 0.6595(3) 0.37369(19) 0.14435(17) 0.0451(6) Uani 1 1 d . . . C3' C 0.7770(3) 0.3917(2) 0.06741(18) 0.0514(6) Uani 1 1 d D . . C4' C 0.8515(4) 0.3965(3) -0.10502(19) 0.0624(7) Uani 1 1 d D . . C5' C 0.7973(4) 0.3889(3) -0.1907(2) 0.0681(8) Uani 1 1 d D . . C6' C 0.6208(4) 0.3677(2) -0.1985(2) 0.0644(8) Uani 1 1 d D . . C7' C 0.4995(4) 0.3512(2) -0.12004(19) 0.0575(7) Uani 1 1 d D . . C8' C 0.5516(3) 0.35667(19) -0.03131(16) 0.0447(6) Uani 1 1 d . . . C9' C 0.7281(3) 0.3819(2) -0.02329(17) 0.0475(6) Uani 1 1 d . . . C10' C 0.6888(3) 0.37618(19) 0.24217(16) 0.0466(6) Uani 1 1 d . . . C11' C 0.5473(4) 0.3705(2) 0.31375(18) 0.0586(7) Uani 1 1 d D . . C12' C 0.5791(4) 0.3740(3) 0.40557(19) 0.0649(8) Uani 1 1 d D . . C13' C 0.7494(4) 0.3835(2) 0.42919(18) 0.0575(7) Uani 1 1 d . . . C14' C 0.8907(4) 0.3871(2) 0.3582(2) 0.0631(7) Uani 1 1 d D . . C15' C 0.8624(4) 0.3833(2) 0.26645(19) 0.0578(7) Uani 1 1 d D . . C16' C 0.7821(6) 0.3921(3) 0.5288(2) 0.0812(10) Uani 1 1 d D . . H3 H 0.224(3) -0.1207(15) 0.6313(18) 0.069(8) Uiso 1 1 d D . . H4 H 0.188(4) -0.1704(17) 0.803(2) 0.100(11) Uiso 1 1 d D . . H5 H 0.180(4) -0.120(2) 0.9590(17) 0.101(11) Uiso 1 1 d D . . H6 H 0.180(4) 0.080(2) 0.9744(15) 0.094(10) Uiso 1 1 d D . . H7 H 0.195(4) 0.2160(16) 0.836(2) 0.081(9) Uiso 1 1 d D . . H11 H 0.239(5) 0.1905(19) 0.414(3) 0.124(13) Uiso 1 1 d D . . H12 H 0.280(5) 0.159(2) 0.2459(19) 0.110(12) Uiso 1 1 d D . . H14 H 0.279(5) -0.1765(19) 0.329(3) 0.130(13) Uiso 1 1 d D . . H15 H 0.254(5) -0.152(2) 0.489(2) 0.115(12) Uiso 1 1 d D . . H16A H 0.306(7) 0.052(2) 0.130(4) 0.25(3) Uiso 1 1 d D . . H16B H 0.194(4) -0.076(3) 0.160(3) 0.166(19) Uiso 1 1 d D . . H16C H 0.421(4) -0.075(3) 0.156(3) 0.19(2) Uiso 1 1 d D . . H3' H 0.903(3) 0.413(2) 0.0727(17) 0.064(8) Uiso 1 1 d D . . H4' H 0.983(3) 0.411(2) -0.096(2) 0.083(9) Uiso 1 1 d D . . H5' H 0.892(3) 0.395(2) -0.2482(16) 0.083(9) Uiso 1 1 d D . . H6' H 0.575(3) 0.364(2) -0.2621(14) 0.071(8) Uiso 1 1 d D . . H7' H 0.368(3) 0.336(2) -0.1230(19) 0.077(9) Uiso 1 1 d D . . H11' H 0.421(3) 0.362(2) 0.2946(19) 0.077(9) Uiso 1 1 d D . . H12' H 0.468(3) 0.368(2) 0.4561(16) 0.075(8) Uiso 1 1 d D . . H14' H 1.019(3) 0.393(2) 0.377(2) 0.083(9) Uiso 1 1 d D . . H15' H 0.970(3) 0.388(2) 0.2150(16) 0.075(8) Uiso 1 1 d D . . H16D H 0.806(5) 0.4765(16) 0.533(3) 0.132(14) Uiso 1 1 d D . . H16E H 0.891(4) 0.338(2) 0.553(3) 0.141(15) Uiso 1 1 d D . . H16F H 0.660(3) 0.376(3) 0.574(2) 0.119(13) Uiso 1 1 d 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 S1 0.0841(6) 0.0532(4) 0.0788(6) -0.0131(4) -0.0045(4) -0.0119(4) O1 0.0683(12) 0.0498(11) 0.0550(11) -0.0049(9) -0.0054(9) -0.0062(9) C1 0.0432(14) 0.0617(17) 0.0584(17) -0.0137(14) -0.0053(12) -0.0037(12) C2 0.0534(15) 0.0482(15) 0.0558(17) -0.0062(13) -0.0057(12) -0.0002(12) C3 0.080(2) 0.0457(16) 0.0587(18) -0.0059(14) -0.0082(14) 0.0023(14) C4 0.112(3) 0.059(2) 0.059(2) -0.0029(16) -0.0044(17) 0.0039(18) C5 0.118(3) 0.084(3) 0.053(2) 0.0009(18) -0.0053(18) 0.005(2) C6 0.094(2) 0.094(3) 0.051(2) -0.0148(19) -0.0058(16) -0.009(2) C7 0.073(2) 0.071(2) 0.064(2) -0.0178(17) -0.0074(15) -0.0116(16) C8 0.0486(15) 0.0539(16) 0.0581(17) -0.0067(13) -0.0051(12) -0.0050(12) C9 0.0654(17) 0.0555(17) 0.0511(17) -0.0047(13) -0.0064(13) 0.0030(13) C10 0.0562(16) 0.0508(16) 0.0521(16) -0.0040(13) -0.0075(12) -0.0020(12) C11 0.113(3) 0.061(2) 0.057(2) -0.0060(16) -0.0075(17) -0.0140(18) C12 0.120(3) 0.073(2) 0.057(2) 0.0061(17) -0.0085(19) -0.015(2) C13 0.0615(17) 0.077(2) 0.0525(17) -0.0097(15) -0.0054(13) 0.0019(15) C14 0.140(3) 0.058(2) 0.062(2) -0.0121(17) -0.009(2) 0.007(2) C15 0.148(3) 0.056(2) 0.0493(19) -0.0034(15) -0.0047(19) 0.006(2) C16 0.097(3) 0.104(3) 0.054(2) -0.0171(19) -0.0057(18) 0.001(2) S1' 0.0489(4) 0.0935(6) 0.0660(5) -0.0101(4) -0.0078(3) -0.0162(4) O1' 0.0447(9) 0.0627(11) 0.0430(10) -0.0069(8) -0.0026(7) -0.0071(8) C1' 0.0491(14) 0.0468(14) 0.0469(15) -0.0060(11) -0.0093(11) 0.0008(11) C2' 0.0432(13) 0.0445(14) 0.0476(15) -0.0053(11) -0.0070(11) -0.0017(11) C3' 0.0441(14) 0.0609(17) 0.0486(16) -0.0055(12) -0.0034(12) -0.0080(12) C4' 0.0562(17) 0.083(2) 0.0464(17) -0.0083(14) 0.0014(13) -0.0077(15) C5' 0.073(2) 0.079(2) 0.0483(18) -0.0094(15) 0.0071(15) -0.0045(16) C6' 0.080(2) 0.0720(19) 0.0432(17) -0.0133(14) -0.0105(15) -0.0050(16) C7' 0.0610(17) 0.0631(17) 0.0510(17) -0.0129(13) -0.0090(14) -0.0063(14) C8' 0.0482(14) 0.0406(13) 0.0447(14) -0.0055(11) -0.0048(11) -0.0005(11) C9' 0.0510(14) 0.0471(14) 0.0432(14) -0.0049(11) -0.0040(11) -0.0014(11) C10' 0.0529(15) 0.0448(14) 0.0418(14) -0.0048(11) -0.0065(11) -0.0018(11) C11' 0.0545(16) 0.0746(19) 0.0450(16) -0.0057(13) -0.0027(13) -0.0042(14) C12' 0.0697(19) 0.078(2) 0.0436(16) -0.0057(14) 0.0043(14) -0.0041(16) C13' 0.080(2) 0.0495(16) 0.0424(15) -0.0042(12) -0.0089(14) -0.0042(14) C14' 0.0659(19) 0.0722(19) 0.0548(18) -0.0098(14) -0.0154(15) -0.0113(15) C15' 0.0555(16) 0.0724(19) 0.0470(16) -0.0098(14) -0.0047(13) -0.0117(14) C16' 0.113(3) 0.086(3) 0.0458(18) -0.0093(17) -0.0146(19) -0.011(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 S1 C1 1.641(3) . ? O1 C1 1.363(3) . ? O1 C2 1.380(3) . ? C1 C8 1.446(4) . ? C2 C3 1.332(4) . ? C2 C10 1.460(4) . ? C3 C9 1.425(4) . ? C3 H3 1.010(17) . ? C4 C5 1.366(4) . ? C4 C9 1.404(4) . ? C4 H4 1.039(18) . ? C5 C6 1.383(5) . ? C5 H5 1.061(18) . ? C6 C7 1.368(4) . ? C6 H6 1.041(18) . ? C7 C8 1.400(4) . ? C7 H7 1.023(17) . ? C8 C9 1.403(4) . ? C10 C15 1.370(4) . ? C10 C11 1.376(4) . ? C11 C12 1.381(4) . ? C11 H11 1.061(19) . ? C12 C13 1.373(4) . ? C12 H12 1.029(18) . ? C13 C14 1.363(4) . ? C13 C16 1.514(4) . ? C14 C15 1.378(4) . ? C14 H14 1.038(19) . ? C15 H15 1.026(18) . ? C16 H16A 1.063(21) . ? C16 H16B 1.067(18) . ? C16 H16C 1.060(19) . ? S1' C1' 1.639(2) . ? O1' C1' 1.359(3) . ? O1' C2' 1.381(3) . ? C1' C8' 1.446(3) . ? C2' C3' 1.336(3) . ? C2' C10' 1.464(3) . ? C3' C9' 1.428(3) . ? C3' H3' 1.008(16) . ? C4' C5' 1.368(4) . ? C4' C9' 1.410(3) . ? C4' H4' 1.041(17) . ? C5' C6' 1.383(4) . ? C5' H5' 1.023(17) . ? C6' C7' 1.368(4) . ? C6' H6' 1.028(17) . ? C7' C8' 1.398(3) . ? C7' H7' 1.021(17) . ? C8' C9' 1.398(3) . ? C10' C11' 1.389(3) . ? C10' C15' 1.394(3) . ? C11' C12' 1.385(4) . ? C11' H11' 1.035(17) . ? C12' C13' 1.372(4) . ? C12' H12' 1.039(17) . ? C13' C14' 1.383(4) . ? C13' C16' 1.511(4) . ? C14' C15' 1.378(4) . ? C14' H14' 1.039(17) . ? C15' H15' 1.029(17) . ? C16' H16D 1.073(18) . ? C16' H16E 1.063(18) . ? C16' H16F 1.067(17) . ? 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 C8 116.7(2) . . ? O1 C1 S1 116.25(19) . . ? O1 C2 C10 111.7(2) . . ? C1 O1 C2 124.4(2) . . ? C2 C3 C9 121.1(3) . . ? C2 C3 H3 118.6(15) . . ? C3 C2 O1 119.4(2) . . ? C3 C2 C10 128.9(2) . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 117.3(18) . . ? C4 C9 C3 122.4(3) . . ? C5 C4 C9 120.6(3) . . ? C5 C4 H4 123.6(18) . . ? C5 C6 H6 121.5(17) . . ? C6 C7 C8 120.4(3) . . ? C6 C7 H7 120.9(16) . . ? C6 C5 H5 122.1(18) . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 118.3(18) . . ? C7 C8 C9 119.6(3) . . ? C7 C8 C1 121.0(3) . . ? C8 C9 C3 119.0(2) . . ? C8 C1 S1 127.1(2) . . ? C8 C9 C4 118.6(3) . . ? C8 C7 H7 118.7(16) . . ? C9 C8 C1 119.4(2) . . ? C9 C4 H4 115.7(18) . . ? C9 C3 H3 120.2(15) . . ? C10 C11 C12 120.7(3) . . ? C10 C11 H11 116(2) . . ? C10 C15 C14 121.1(3) . . ? C10 C15 H15 121(2) . . ? C11 C10 C2 121.8(2) . . ? C11 C12 H12 122(2) . . ? C12 C11 H11 123(2) . . ? C12 C13 C16 121.8(3) . . ? C13 C14 C15 122.2(3) . . ? C13 C14 H14 118(2) . . ? C13 C12 C11 122.1(3) . . ? C13 C12 H12 116(2) . . ? C13 C16 H16A 108(3) . . ? C13 C16 H16B 111(2) . . ? C13 C16 H16C 110(3) . . ? C14 C13 C12 116.4(3) . . ? C14 C13 C16 121.7(3) . . ? C14 C15 H15 118(2) . . ? C15 C10 C11 117.4(3) . . ? C15 C10 C2 120.9(2) . . ? C15 C14 H14 120(2) . . ? H16A C16 H16B 115(3) . . ? H16A C16 H16C 108(3) . . ? H16B C16 H16C 105(3) . . ? O1' C1' C8' 117.8(2) . . ? O1' C1' S1' 116.14(18) . . ? O1' C2' C10' 112.07(19) . . ? C1' O1' C2' 123.44(18) . . ? C2' C3' C9' 121.3(2) . . ? C2' C3' H3' 120.0(15) . . ? C3' C2' O1' 119.5(2) . . ? C3' C2' C10' 128.4(2) . . ? C4' C5' C6' 120.6(3) . . ? C4' C9' C3' 122.4(2) . . ? C4' C5' H5' 118.6(16) . . ? C5' C4' C9' 120.3(3) . . ? C5' C4' H4' 123.0(16) . . ? C5' C6' H6' 122.4(15) . . ? C6' C7' C8' 120.5(3) . . ? C6' C7' H7' 122.5(16) . . ? C6' C5' H5' 120.7(16) . . ? C7' C6' C5' 120.2(3) . . ? C7' C6' H6' 117.4(15) . . ? C7' C8' C1' 121.4(2) . . ? C8' C9' C4' 118.8(2) . . ? C8' C9' C3' 118.8(2) . . ? C8' C1' S1' 126.01(18) . . ? C8' C7' H7' 117.0(16) . . ? C9' C8' C7' 119.6(2) . . ? C9' C8' C1' 119.0(2) . . ? C9' C3' H3' 118.7(15) . . ? C9' C4' H4' 116.7(16) . . ? C10' C11' H11' 116.4(16) . . ? C10' C15' H15' 119.6(15) . . ? C13' C16' H16D 109(2) . . ? C13' C16' H16E 113(2) . . ? C11' C10' C15' 117.7(2) . . ? C11' C10' C2' 121.9(2) . . ? C11' C12' H12' 116.9(15) . . ? C12' C13' C14' 117.7(2) . . ? C12' C13' C16' 121.5(3) . . ? C12' C11' C10' 120.5(3) . . ? C12' C11' H11' 123.1(16) . . ? C13' C12' C11' 121.7(3) . . ? C13' C12' H12' 121.4(15) . . ? C13' C14' H14' 116.9(16) . . ? C13' C16' H16F 109(2) . . ? C14' C15' C10' 120.7(3) . . ? C14' C15' H15' 119.6(15) . . ? C14' C13' C16' 120.8(3) . . ? C15' C14' C13' 121.6(3) . . ? C15' C14' H14' 121.5(16) . . ? C15' C10' C2' 120.4(2) . . ? H16D C16' H16E 110(2) . . ? H16D C16' H16F 105(2) . . ? H16E C16' H16F 110(2) . . ? 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 S1 C1 C8 C7 1.0(4) . . . . ? S1 C1 C8 C9 -177.4(2) . . . . ? O1 C1 C8 C9 2.4(3) . . . . ? O1 C2 C3 C9 0.3(4) . . . . ? O1 C1 C8 C7 -179.2(2) . . . . ? O1 C2 C10 C15 177.4(3) . . . . ? O1 C2 C10 C11 -3.2(4) . . . . ? C1 O1 C2 C3 0.9(4) . . . . ? C1 C8 C9 C3 -1.4(4) . . . . ? C1 C8 C9 C4 178.5(3) . . . . ? C1 O1 C2 C10 -178.7(2) . . . . ? C2 O1 C1 C8 -2.2(3) . . . . ? C2 O1 C1 S1 177.64(18) . . . . ? C2 C10 C11 C12 180.0(3) . . . . ? C2 C3 C9 C8 0.0(4) . . . . ? C2 C3 C9 C4 -179.9(3) . . . . ? C2 C10 C15 C14 -179.6(3) . . . . ? C3 C2 C10 C15 -2.2(5) . . . . ? C3 C2 C10 C11 177.2(3) . . . . ? C4 C5 C6 C7 -0.3(6) . . . . ? C5 C6 C7 C8 -0.8(5) . . . . ? C5 C4 C9 C8 -1.3(5) . . . . ? C5 C4 C9 C3 178.7(3) . . . . ? C6 C7 C8 C9 0.9(4) . . . . ? C6 C7 C8 C1 -177.4(3) . . . . ? C7 C8 C9 C4 0.1(4) . . . . ? C7 C8 C9 C3 -179.8(3) . . . . ? C9 C4 C5 C6 1.4(6) . . . . ? C10 C2 C3 C9 179.9(2) . . . . ? C10 C11 C12 C13 0.1(6) . . . . ? C11 C12 C13 C14 0.0(5) . . . . ? C11 C12 C13 C16 179.6(3) . . . . ? C11 C10 C15 C14 0.9(5) . . . . ? C12 C13 C14 C15 0.4(6) . . . . ? C13 C14 C15 C10 -0.9(6) . . . . ? C15 C10 C11 C12 -0.6(5) . . . . ? C16 C13 C14 C15 -179.2(3) . . . . ? S1' C1' C8' C7' 3.6(4) . . . . ? S1' C1' C8' C9' -175.12(19) . . . . ? O1' C1' C8' C7' -177.9(2) . . . . ? O1' C1' C8' C9' 3.4(3) . . . . ? O1' C2' C3' C9' -0.2(4) . . . . ? O1' C2' C10' C11' -10.9(3) . . . . ? O1' C2' C10' C15' 168.4(2) . . . . ? C1' O1' C2' C3' -0.2(3) . . . . ? C1' O1' C2' C10' -178.3(2) . . . . ? C1' C8' C9' C4' 176.0(2) . . . . ? C1' C8' C9' C3' -3.8(3) . . . . ? C2' O1' C1' C8' -1.4(3) . . . . ? C2' O1' C1' S1' 177.26(17) . . . . ? C2' C3' C9' C8' 2.3(4) . . . . ? C2' C3' C9' C4' -177.6(3) . . . . ? C2' C10' C15' C14' 179.2(2) . . . . ? C2' C10' C11' C12' -179.4(2) . . . . ? C3' C2' C10' C11' 171.1(3) . . . . ? C3' C2' C10' C15' -9.5(4) . . . . ? C4' C5' C6' C7' -1.7(5) . . . . ? C5' C6' C7' C8' 0.7(4) . . . . ? C5' C4' C9' C8' 1.8(4) . . . . ? C5' C4' C9' C3' -178.4(3) . . . . ? C6' C7' C8' C9' 1.5(4) . . . . ? C6' C7' C8' C1' -177.2(2) . . . . ? C7' C8' C9' C4' -2.7(4) . . . . ? C7' C8' C9' C3' 177.4(2) . . . . ? C9' C4' C5' C6' 0.4(5) . . . . ? C10' C2' C3' C9' 177.6(2) . . . . ? C10' C11' C12' C13' 0.2(4) . . . . ? C11' C12' C13' C14' -1.3(4) . . . . ? C11' C12' C13' C16' 177.4(3) . . . . ? C11' C10' C15' C14' -1.5(4) . . . . ? C12' C13' C14' C15' 1.1(4) . . . . ? C13' C14' C15' C10' 0.4(4) . . . . ? C15' C10' C11' C12' 1.2(4) . . . . ? C16' C13' C14' C15' -177.7(3) . . . . ? #===END # Attachment 'TI-3.cif' data_vh3n_m _database_code_depnum_ccdc_archive 'CCDC 656922' #============================================================================== _audit_creation_date 'Aug 07 17:24:12 2008' _audit_creation_method ' SHELXL-97' _audit_update_record ; ; #=============================================================================== _chemical_name_systematic ; ; _chemical_name_common 3-(4-methoxyphenyl)-1H-isochromene-1-thione _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 O2 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C16 H12 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 268.33 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z _cell_length_a 7.5948(14) _cell_length_b 10.988(2) _cell_length_c 15.526(3) _cell_angle_alpha 90 _cell_angle_beta 96.149(3) _cell_angle_gamma 90 _cell_volume 1288.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 928 _cell_measurement_theta_min 2.62 _cell_measurement_theta_max 26.71 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.245 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9025 _exptl_absorpt_correction_T_max 0.9807 #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 9306 _diffrn_reflns_av_R_equivalents 0.0231 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2389 # number of observed reflections (> n sig(I)) _reflns_number_gt 1850 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== _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^)+(0.0547P)^2^+0.1537P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2389 _refine_ls_number_parameters 220 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.173 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.035 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.08808(9) 0.34050(4) 1.02103(3) 0.0712(2) Uani 1 1 d . . . O1 O 0.20393(16) 0.13455(10) 0.97464(7) 0.0461(3) Uani 1 1 d . . . O2 O 0.4545(2) -0.17482(13) 0.66789(10) 0.0708(4) Uani 1 1 d . . . C1 C 0.1455(2) 0.19794(16) 1.04142(11) 0.0452(4) Uani 1 1 d . . . C2 C 0.2499(2) 0.01247(14) 0.97930(10) 0.0413(4) Uani 1 1 d . . . C3 C 0.2391(2) -0.04893(16) 1.05298(12) 0.0463(4) Uani 1 1 d D . . C4 C 0.1790(3) -0.05020(19) 1.20708(12) 0.0554(5) Uani 1 1 d D . . C5 C 0.1307(3) 0.0107(2) 1.27784(13) 0.0601(5) Uani 1 1 d D . . C6 C 0.0870(3) 0.1336(2) 1.27272(12) 0.0576(5) Uani 1 1 d D . . C7 C 0.0895(3) 0.19460(18) 1.19576(11) 0.0507(5) Uani 1 1 d D . . C8 C 0.1397(2) 0.13460(15) 1.12248(10) 0.0418(4) Uani 1 1 d . . . C9 C 0.1856(2) 0.01050(15) 1.12811(10) 0.0439(4) Uani 1 1 d . . . C10 C 0.3049(2) -0.03198(15) 0.89747(11) 0.0425(4) Uani 1 1 d . . . C11 C 0.2971(2) 0.04057(16) 0.82431(11) 0.0473(4) Uani 1 1 d D . . C12 C 0.3448(2) -0.00321(17) 0.74612(12) 0.0517(5) Uani 1 1 d D . . C13 C 0.4048(2) -0.12151(17) 0.74119(13) 0.0518(5) Uani 1 1 d . . . C14 C 0.4171(3) -0.19468(18) 0.81400(14) 0.0569(5) Uani 1 1 d D . . C15 C 0.3668(2) -0.15162(16) 0.89075(13) 0.0517(5) Uani 1 1 d D . . C16 C 0.4555(4) -0.1014(3) 0.59251(16) 0.0819(7) Uani 1 1 d D . . H3 H 0.274(3) -0.1368(14) 1.0559(12) 0.061(5) Uiso 1 1 d D . . H4 H 0.213(2) -0.1389(14) 1.2081(12) 0.059(5) Uiso 1 1 d D . . H5 H 0.125(3) -0.0325(17) 1.3333(10) 0.067(6) Uiso 1 1 d D . . H6 H 0.052(3) 0.1808(17) 1.3232(12) 0.074(6) Uiso 1 1 d D . . H7 H 0.051(2) 0.2823(15) 1.1888(13) 0.068(6) Uiso 1 1 d D . . H11 H 0.253(2) 0.1292(14) 0.8270(12) 0.061(5) Uiso 1 1 d D . . H12 H 0.330(2) 0.0534(17) 0.6949(11) 0.067(6) Uiso 1 1 d D . . H14 H 0.462(2) -0.2803(15) 0.8101(13) 0.072(6) Uiso 1 1 d D . . H15 H 0.377(3) -0.2066(18) 0.9424(12) 0.074(6) Uiso 1 1 d D . . H16A H 0.516(4) -0.155(2) 0.5490(16) 0.131(11) Uiso 1 1 d D . . H16B H 0.325(2) -0.085(2) 0.5654(14) 0.089(8) Uiso 1 1 d D . . H16C H 0.529(3) -0.0211(19) 0.6040(17) 0.112(9) Uiso 1 1 d 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 S1 0.1242(5) 0.0413(3) 0.0512(3) 0.0029(2) 0.0240(3) 0.0200(3) O1 0.0620(8) 0.0355(6) 0.0411(6) -0.0022(5) 0.0082(5) 0.0053(5) O2 0.0770(10) 0.0671(9) 0.0716(10) -0.0281(8) 0.0229(8) -0.0005(7) C1 0.0523(10) 0.0410(9) 0.0425(9) -0.0048(7) 0.0053(8) -0.0008(7) C2 0.0379(9) 0.0349(9) 0.0499(10) -0.0020(7) -0.0002(7) -0.0007(7) C3 0.0447(10) 0.0370(9) 0.0566(11) 0.0011(8) 0.0020(8) 0.0023(7) C4 0.0568(12) 0.0543(12) 0.0541(11) 0.0120(9) 0.0017(9) -0.0028(9) C5 0.0604(12) 0.0736(14) 0.0454(11) 0.0147(10) 0.0019(9) -0.0149(10) C6 0.0618(12) 0.0684(13) 0.0428(10) -0.0036(9) 0.0073(9) -0.0113(10) C7 0.0565(12) 0.0524(11) 0.0434(10) -0.0030(8) 0.0059(8) -0.0047(9) C8 0.0411(9) 0.0429(9) 0.0405(9) -0.0005(7) 0.0002(7) -0.0044(7) C9 0.0378(9) 0.0458(10) 0.0469(9) 0.0050(8) -0.0012(7) -0.0054(7) C10 0.0360(9) 0.0383(9) 0.0526(10) -0.0063(8) 0.0015(7) -0.0018(7) C11 0.0486(10) 0.0391(9) 0.0549(11) -0.0056(8) 0.0095(8) 0.0006(8) C12 0.0554(11) 0.0458(11) 0.0554(11) -0.0085(9) 0.0138(9) -0.0058(8) C13 0.0424(10) 0.0500(10) 0.0638(12) -0.0191(9) 0.0102(8) -0.0052(8) C14 0.0534(12) 0.0428(10) 0.0740(13) -0.0146(10) 0.0044(10) 0.0084(9) C15 0.0535(11) 0.0414(10) 0.0591(11) -0.0018(9) 0.0009(9) 0.0058(8) C16 0.094(2) 0.0929(19) 0.0623(15) -0.0259(14) 0.0237(14) -0.0102(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.6477(18) . ? O1 C1 1.3621(19) . ? O1 C2 1.3860(18) . ? O2 C13 1.368(2) . ? O2 C16 1.422(3) . ? C1 C8 1.443(2) . ? C2 C3 1.338(2) . ? C2 C10 1.463(2) . ? C3 C9 1.433(2) . ? C3 H3 1.002(14) . ? C4 C5 1.370(3) . ? C4 C9 1.401(2) . ? C4 H4 1.008(14) . ? C5 C6 1.390(3) . ? C5 H5 0.987(15) . ? C6 C7 1.372(3) . ? C6 H6 0.998(15) . ? C7 C8 1.403(2) . ? C7 H7 1.010(15) . ? C8 C9 1.408(2) . ? C10 C11 1.384(2) . ? C10 C15 1.404(2) . ? C11 C12 1.390(2) . ? C11 H11 1.033(14) . ? C12 C13 1.382(3) . ? C12 H12 1.007(15) . ? C13 C14 1.382(3) . ? C14 C15 1.374(3) . ? C14 H14 1.006(15) . ? C15 H15 1.001(15) . ? C16 H16A 1.040(18) . ? C16 H16B 1.049(16) . ? C16 H16C 1.051(17) . ? 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 C8 117.40(15) . . ? O1 C1 S1 116.17(12) . . ? O1 C2 C10 111.81(14) . . ? O2 C13 C14 115.52(17) . . ? O2 C16 H16A 104.6(16) . . ? O2 C16 H16C 112.7(15) . . ? O2 C16 H16B 109.7(13) . . ? O2 C13 C12 124.79(19) . . ? C1 O1 C2 123.77(13) . . ? C2 C3 C9 120.98(16) . . ? C2 C3 H3 118.9(11) . . ? C3 C2 O1 119.63(15) . . ? C3 C2 C10 128.56(16) . . ? C4 C5 C6 120.77(18) . . ? C4 C9 C8 118.91(16) . . ? C4 C9 C3 122.36(17) . . ? C4 C5 H5 120.2(12) . . ? C5 C4 C9 120.46(19) . . ? C5 C4 H4 123.4(11) . . ? C5 C6 H6 122.8(12) . . ? C6 C7 C8 120.46(19) . . ? C6 C7 H7 121.9(11) . . ? C6 C5 H5 119.0(12) . . ? C7 C6 C5 119.92(19) . . ? C7 C6 H6 117.3(12) . . ? C7 C8 C9 119.47(15) . . ? C7 C8 C1 121.14(16) . . ? C8 C1 S1 126.44(13) . . ? C8 C9 C3 118.73(15) . . ? C8 C7 H7 117.6(11) . . ? C9 C3 H3 120.1(11) . . ? C9 C4 H4 116.2(11) . . ? C9 C8 C1 119.39(15) . . ? C10 C11 C12 121.69(17) . . ? C10 C11 H11 119.7(10) . . ? C10 C15 H15 120.2(12) . . ? C11 C10 C15 117.63(16) . . ? C11 C10 C2 121.95(15) . . ? C11 C12 H12 117.4(11) . . ? C12 C11 H11 118.6(11) . . ? C13 C12 C11 119.50(18) . . ? C13 O2 C16 117.88(17) . . ? C13 C12 H12 123.1(11) . . ? C13 C14 H14 119.2(11) . . ? C14 C15 C10 120.89(18) . . ? C14 C15 H15 118.9(12) . . ? C14 C13 C12 119.69(17) . . ? C15 C14 C13 120.56(17) . . ? C15 C14 H14 120.2(12) . . ? C15 C10 C2 120.41(16) . . ? H16A C16 H16B 107(2) . . ? H16A C16 H16C 109(2) . . ? H16B C16 H16C 113(2) . . ? 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 S1 C1 C8 C7 -3.2(3) . . . . ? S1 C1 C8 C9 176.97(14) . . . . ? O1 C1 C8 C9 -3.0(2) . . . . ? O1 C2 C3 C9 -1.8(2) . . . . ? O1 C2 C10 C11 -4.4(2) . . . . ? O1 C1 C8 C7 176.88(15) . . . . ? O1 C2 C10 C15 176.12(15) . . . . ? O2 C13 C14 C15 -178.47(17) . . . . ? C1 O1 C2 C3 -0.6(2) . . . . ? C1 C8 C9 C4 -179.82(16) . . . . ? C1 O1 C2 C10 179.00(14) . . . . ? C1 C8 C9 C3 0.8(2) . . . . ? C2 C3 C9 C4 -177.71(16) . . . . ? C2 C3 C9 C8 1.7(2) . . . . ? C2 O1 C1 C8 3.0(2) . . . . ? C2 O1 C1 S1 -176.96(12) . . . . ? C2 C10 C11 C12 -178.16(15) . . . . ? C2 C10 C15 C14 179.33(16) . . . . ? C3 C2 C10 C11 175.19(17) . . . . ? C3 C2 C10 C15 -4.3(3) . . . . ? C4 C5 C6 C7 0.9(3) . . . . ? C5 C6 C7 C8 -1.4(3) . . . . ? C5 C4 C9 C8 -0.8(3) . . . . ? C5 C4 C9 C3 178.61(17) . . . . ? C6 C7 C8 C9 0.8(3) . . . . ? C6 C7 C8 C1 -179.08(17) . . . . ? C7 C8 C9 C4 0.3(2) . . . . ? C7 C8 C9 C3 -179.09(16) . . . . ? C9 C4 C5 C6 0.2(3) . . . . ? C10 C2 C3 C9 178.64(15) . . . . ? C10 C11 C12 C13 -1.2(3) . . . . ? C11 C12 C13 O2 179.60(16) . . . . ? C11 C12 C13 C14 -0.1(3) . . . . ? C11 C10 C15 C14 -0.2(3) . . . . ? C12 C13 C14 C15 1.3(3) . . . . ? C13 C14 C15 C10 -1.1(3) . . . . ? C15 C10 C11 C12 1.4(3) . . . . ? C16 O2 C13 C14 -176.01(19) . . . . ? C16 O2 C13 C12 4.2(3) . . . . ? #===END # Attachment 'TI-4.cif' data_vh6_m _database_code_depnum_ccdc_archive 'CCDC 656924' #============================================================================== _audit_creation_date 'Aug 07 23:30:28 2008' _audit_creation_method ' SHELXL-97' _audit_update_record ; ; _chemical_name_systematic ; ; _chemical_name_common '3-(2- Furyl)-1H-isochromene-1-thione' _chemical_melting_point ? _chemical_formula_moiety 'C13 H8 O2 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C13 H8 O2 S' _chemical_formula_iupac ? _chemical_formula_weight 228.26 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 4.0478(6) _cell_length_b 13.5257(19) _cell_length_c 19.180(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1050.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 2624 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 24.05 _cell_special_details ; ; _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.06 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.286 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9141 _exptl_absorpt_correction_T_max 0.9830 #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 7813 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1945 # number of observed reflections (> n sig(I)) _reflns_number_gt 1710 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== _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^)+(0.0322P)^2^+0.0944P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack(1983), 758 Friedel pairs' _refine_ls_abs_structure_Flack -0.04(9) _refine_ls_number_reflns 1945 _refine_ls_number_parameters 177 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0722 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.118 _refine_diff_density_min -0.113 _refine_diff_density_rms 0.029 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.87860(18) -0.07987(4) 0.15159(3) 0.0610(2) Uani 1 1 d . . . O1 O 0.9201(4) 0.02890(10) 0.26012(7) 0.0486(4) Uani 1 1 d . . . O2 O 0.9957(5) 0.16943(11) 0.41637(7) 0.0638(5) Uani 1 1 d . . . C1 C 0.8077(5) 0.02349(14) 0.19267(10) 0.0433(5) Uani 1 1 d . . . C2 C 0.8757(6) 0.11190(14) 0.30117(10) 0.0432(5) Uani 1 1 d . . . C3 C 0.7163(6) 0.19112(15) 0.27829(11) 0.0462(6) Uani 1 1 d D . . C4 C 0.4219(6) 0.27534(15) 0.18090(12) 0.0521(6) Uani 1 1 d D . . C5 C 0.3109(7) 0.27494(18) 0.11352(13) 0.0568(6) Uani 1 1 d D . . C6 C 0.3606(6) 0.19196(17) 0.07139(12) 0.0538(6) Uani 1 1 d D . . C7 C 0.5197(6) 0.11057(16) 0.09707(11) 0.0485(5) Uani 1 1 d D . . C8 C 0.6372(5) 0.11000(14) 0.16583(10) 0.0407(5) Uani 1 1 d . . . C9 C 0.5892(6) 0.19315(14) 0.20844(10) 0.0423(5) Uani 1 1 d . . . C10 C 1.0296(6) 0.09532(16) 0.36820(10) 0.0470(5) Uani 1 1 d . . . C11 C 1.2098(6) 0.02103(18) 0.39443(12) 0.0553(6) Uani 1 1 d D . . C12 C 1.2970(7) 0.0489(2) 0.46331(13) 0.0672(7) Uani 1 1 d D . . C13 C 1.1652(8) 0.1365(2) 0.47440(12) 0.0726(8) Uani 1 1 d D . . H3 H 0.685(6) 0.2519(12) 0.3070(10) 0.058(6) Uiso 1 1 d D . . H4 H 0.397(7) 0.3362(13) 0.2113(10) 0.078(8) Uiso 1 1 d D . . H5 H 0.176(5) 0.3327(14) 0.0950(11) 0.072(7) Uiso 1 1 d D . . H6 H 0.280(6) 0.1937(16) 0.0222(8) 0.065(7) Uiso 1 1 d D . . H7 H 0.550(6) 0.0494(12) 0.0685(9) 0.057(6) Uiso 1 1 d D . . H11 H 1.273(6) -0.0409(14) 0.3705(11) 0.074(8) Uiso 1 1 d D . . H12 H 1.441(6) 0.0105(15) 0.4981(10) 0.065(7) Uiso 1 1 d D . . H13 H 1.151(7) 0.1873(15) 0.5141(10) 0.083(8) Uiso 1 1 d 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 S1 0.0836(5) 0.0474(3) 0.0520(3) -0.0048(3) 0.0025(3) 0.0104(3) O1 0.0594(10) 0.0457(8) 0.0407(8) 0.0021(6) -0.0016(8) 0.0023(8) O2 0.0824(12) 0.0651(10) 0.0440(9) -0.0060(7) -0.0021(9) -0.0076(9) C1 0.0464(13) 0.0462(12) 0.0373(11) 0.0029(9) 0.0066(10) -0.0046(10) C2 0.0462(13) 0.0440(11) 0.0395(10) 0.0006(9) 0.0071(10) -0.0089(11) C3 0.0540(15) 0.0395(11) 0.0451(12) -0.0025(10) 0.0072(11) -0.0072(10) C4 0.0546(16) 0.0438(12) 0.0578(14) 0.0034(10) 0.0092(13) 0.0026(12) C5 0.0500(15) 0.0536(14) 0.0669(16) 0.0178(12) 0.0036(13) 0.0038(12) C6 0.0494(14) 0.0651(14) 0.0468(13) 0.0112(11) 0.0002(12) -0.0019(13) C7 0.0493(13) 0.0519(13) 0.0442(12) 0.0012(10) 0.0012(11) -0.0030(11) C8 0.0373(11) 0.0441(11) 0.0408(10) 0.0046(8) 0.0073(9) -0.0054(10) C9 0.0415(13) 0.0432(11) 0.0423(11) 0.0055(9) 0.0096(10) -0.0061(10) C10 0.0517(13) 0.0516(13) 0.0376(10) 0.0008(9) 0.0060(10) -0.0123(11) C11 0.0526(15) 0.0620(15) 0.0514(14) 0.0068(12) 0.0016(12) -0.0057(13) C12 0.0580(17) 0.094(2) 0.0501(15) 0.0168(14) -0.0073(13) -0.0146(16) C13 0.087(2) 0.090(2) 0.0402(13) -0.0016(14) -0.0050(15) -0.0186(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C1 1.630(2) . ? O1 C1 1.373(2) . ? O1 C2 1.383(2) . ? O2 C10 1.370(2) . ? O2 C13 1.381(3) . ? C1 C8 1.453(3) . ? C2 C3 1.326(3) . ? C2 C10 1.446(3) . ? C3 C9 1.435(3) . ? C3 H3 0.997(15) . ? C4 C5 1.368(3) . ? C4 C9 1.405(3) . ? C4 H4 1.014(16) . ? C5 C6 1.397(3) . ? C5 H5 1.018(16) . ? C6 C7 1.367(3) . ? C6 H6 1.000(15) . ? C7 C8 1.402(3) . ? C7 H7 0.999(15) . ? C8 C9 1.404(3) . ? C10 C11 1.340(3) . ? C11 C12 1.418(3) . ? C11 H11 0.989(16) . ? C12 C13 1.317(4) . ? C12 H12 1.026(16) . ? C13 H13 1.028(16) . ? 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 C8 116.63(17) . . ? O1 C1 S1 116.27(15) . . ? O1 C2 C10 108.93(17) . . ? O2 C10 C2 116.29(19) . . ? O2 C13 H13 110.8(14) . . ? C1 O1 C2 122.45(15) . . ? C2 C3 C9 119.93(19) . . ? C2 C3 H3 123.0(12) . . ? C3 C2 O1 122.07(18) . . ? C3 C2 C10 129.00(19) . . ? C4 C5 C6 120.1(2) . . ? C4 C5 H5 120.2(13) . . ? C4 C9 C3 122.61(19) . . ? C5 C4 C9 120.7(2) . . ? C5 C4 H4 121.0(13) . . ? C5 C6 H6 118.7(13) . . ? C6 C7 C8 120.2(2) . . ? C6 C7 H7 121.8(12) . . ? C6 C5 H5 119.5(13) . . ? C7 C6 C5 120.4(2) . . ? C7 C6 H6 120.9(13) . . ? C7 C8 C9 119.75(19) . . ? C7 C8 C1 119.93(18) . . ? C8 C1 S1 127.10(15) . . ? C8 C7 H7 117.9(12) . . ? C8 C9 C4 118.80(19) . . ? C8 C9 C3 118.59(18) . . ? C9 C4 H4 118.2(13) . . ? C9 C3 H3 117.0(12) . . ? C9 C8 C1 120.32(18) . . ? C10 O2 C13 104.95(19) . . ? C10 C11 C12 106.6(2) . . ? C10 C11 H11 127.1(14) . . ? C11 C10 O2 110.49(19) . . ? C11 C10 C2 133.2(2) . . ? C11 C12 H12 127.8(13) . . ? C12 C13 O2 111.2(2) . . ? C12 C13 H13 138.1(14) . . ? C12 C11 H11 126.3(14) . . ? C13 C12 C11 106.8(3) . . ? C13 C12 H12 125.4(12) . . ? 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 S1 C1 C8 C9 178.63(16) . . . . ? S1 C1 C8 C7 -1.4(3) . . . . ? O1 C2 C3 C9 -1.2(3) . . . . ? O1 C1 C8 C7 179.04(19) . . . . ? O1 C1 C8 C9 -1.0(3) . . . . ? O1 C2 C10 C11 3.9(3) . . . . ? O1 C2 C10 O2 -177.34(17) . . . . ? O2 C10 C11 C12 0.0(3) . . . . ? C1 C8 C9 C4 -179.7(2) . . . . ? C1 C8 C9 C3 0.9(3) . . . . ? C1 O1 C2 C3 1.2(3) . . . . ? C1 O1 C2 C10 -178.36(18) . . . . ? C2 O1 C1 C8 -0.1(3) . . . . ? C2 C10 C11 C12 178.8(2) . . . . ? C2 O1 C1 S1 -179.69(15) . . . . ? C2 C3 C9 C8 0.2(3) . . . . ? C2 C3 C9 C4 -179.2(2) . . . . ? C3 C2 C10 C11 -175.6(3) . . . . ? C3 C2 C10 O2 3.2(3) . . . . ? C4 C5 C6 C7 0.1(4) . . . . ? C5 C6 C7 C8 -0.6(4) . . . . ? C5 C4 C9 C8 -0.8(3) . . . . ? C5 C4 C9 C3 178.6(2) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C6 C7 C8 C1 -179.6(2) . . . . ? C7 C8 C9 C4 0.3(3) . . . . ? C7 C8 C9 C3 -179.1(2) . . . . ? C9 C4 C5 C6 0.6(4) . . . . ? C10 C2 C3 C9 178.2(2) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C10 O2 C13 C12 0.4(3) . . . . ? C11 C12 C13 O2 -0.4(3) . . . . ? C13 O2 C10 C11 -0.2(3) . . . . ? C13 O2 C10 C2 -179.3(2) . . . . ? #===END # Attachment 'TI-5.cif' data_vh4_m _database_code_depnum_ccdc_archive 'CCDC 658572' #============================================================================== _audit_creation_date 'Aug 07 22:53:33 2008' _audit_creation_method ' SHELXL-97' _audit_update_record ; ; _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H10 O S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C15 H10 O S' _chemical_formula_iupac ? _chemical_formula_weight 238.30 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,1/2+y,1/2-z 3 -x,-y,-z 4 1/2+x,1/2-y,1/2+z _cell_length_a 3.8992(5) _cell_length_b 15.2947(18) _cell_length_c 19.007(2) _cell_angle_alpha 90 _cell_angle_beta 92.701(2) _cell_angle_gamma 90 _cell_volume 1132.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 958 _cell_measurement_theta_min 1.73 _cell_measurement_theta_max 24.18 _cell_special_details ; ; _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.263 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_absorpt_correction_T_min 0.9426 _exptl_absorpt_correction_T_max 0.9922 #=============================================================================== _exptl_special_details ; ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? _diffrn_reflns_number 7940 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.0640 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 1998 # number of observed reflections (> n sig(I)) _reflns_number_gt 1301 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART V5.628, (Bruker, 2004)' _computing_cell_refinement 'Bruker SMART V5.628, (Bruker, 2004)' _computing_data_reduction 'Bruker SAINT V6.45a, (Bruker, 2004)' _computing_structure_solution 'SHELXTL V6.14 (Bruker, 2000)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 1990)' #=============================================================================== _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^)+(0.0548P)^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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1998 _refine_ls_number_parameters 194 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.1249 _refine_ls_R_factor_gt 0.0752 _refine_ls_wR_factor_ref 0.1519 _refine_ls_wR_factor_gt 0.1375 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.160 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.234 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.053 #=============================================================================== loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.0978(3) -0.14695(7) 0.79040(6) 0.0592(4) Uani 1 1 d . . . O1 O 0.1255(6) 0.01126(15) 0.83289(12) 0.0436(7) Uani 1 1 d . . . C1 C 0.0167(9) -0.0430(2) 0.77922(18) 0.0394(9) Uani 1 1 d . . . C2 C 0.0867(9) 0.1014(2) 0.83110(18) 0.0363(9) Uani 1 1 d . . . C3 C -0.0619(9) 0.1400(2) 0.77465(18) 0.0396(9) Uani 1 1 d D . . C4 C -0.3482(10) 0.1281(3) 0.6559(2) 0.0480(11) Uani 1 1 d D . . C5 C -0.4711(10) 0.0772(3) 0.6006(2) 0.0520(11) Uani 1 1 d D . . C6 C -0.4406(10) -0.0129(3) 0.6038(2) 0.0532(11) Uani 1 1 d D . . C7 C -0.2841(10) -0.0528(3) 0.6618(2) 0.0485(11) Uani 1 1 d D . . C8 C -0.1531(9) -0.0016(2) 0.71811(18) 0.0375(9) Uani 1 1 d . . . C9 C -0.1894(9) 0.0892(2) 0.71545(18) 0.0360(9) Uani 1 1 d . . . C10 C 0.2211(8) 0.1419(2) 0.89684(18) 0.0372(9) Uani 1 1 d . . . C11 C 0.2591(11) 0.0939(3) 0.9587(2) 0.0499(11) Uani 1 1 d D . . C12 C 0.3819(11) 0.1329(3) 1.0208(2) 0.0581(12) Uani 1 1 d D . . C13 C 0.4731(11) 0.2192(3) 1.0209(2) 0.0556(12) Uani 1 1 d D . . C14 C 0.4381(10) 0.2676(3) 0.9600(2) 0.0558(11) Uani 1 1 d D . . C15 C 0.3127(10) 0.2295(3) 0.8980(2) 0.0476(10) Uani 1 1 d D . . H3 H -0.100(8) 0.2074(13) 0.7718(18) 0.049(10) Uiso 1 1 d D . . H4 H -0.370(9) 0.1964(13) 0.652(2) 0.061(12) Uiso 1 1 d D . . H5 H -0.595(9) 0.105(2) 0.5559(15) 0.081(14) Uiso 1 1 d D . . H6 H -0.535(9) -0.054(2) 0.5645(15) 0.058(11) Uiso 1 1 d D . . H7 H -0.271(9) -0.1197(13) 0.6647(19) 0.054(11) Uiso 1 1 d D . . H11 H 0.196(9) 0.0274(14) 0.956(2) 0.071(13) Uiso 1 1 d D . . H12 H 0.417(10) 0.089(2) 1.0631(17) 0.087(15) Uiso 1 1 d D . . H13 H 0.582(8) 0.249(2) 1.0655(14) 0.067(12) Uiso 1 1 d D . . H14 H 0.513(8) 0.3330(14) 0.9608(19) 0.060(11) Uiso 1 1 d D . . H15 H 0.309(8) 0.266(2) 0.8509(13) 0.057(11) Uiso 1 1 d 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 S1 0.0946(9) 0.0356(6) 0.0464(6) 0.0019(5) -0.0089(6) 0.0016(6) O1 0.0631(18) 0.0374(16) 0.0296(14) -0.0013(12) -0.0064(12) -0.0001(13) C1 0.046(2) 0.038(2) 0.034(2) -0.0002(17) 0.0032(18) -0.0043(18) C2 0.040(2) 0.033(2) 0.035(2) -0.0016(17) 0.0042(17) -0.0010(17) C3 0.051(2) 0.030(2) 0.037(2) 0.0029(18) 0.0000(17) 0.0026(19) C4 0.056(3) 0.053(3) 0.035(2) 0.004(2) -0.0018(19) 0.008(2) C5 0.059(3) 0.064(3) 0.033(2) 0.001(2) -0.006(2) 0.012(2) C6 0.059(3) 0.062(3) 0.038(2) -0.009(2) -0.003(2) -0.001(2) C7 0.060(3) 0.046(3) 0.040(2) -0.004(2) 0.001(2) -0.002(2) C8 0.042(2) 0.040(2) 0.0302(19) 0.0006(18) 0.0030(16) 0.0011(17) C9 0.037(2) 0.041(2) 0.0309(19) -0.0027(17) 0.0051(16) 0.0033(16) C10 0.036(2) 0.040(2) 0.035(2) -0.0044(18) 0.0021(16) -0.0002(18) C11 0.072(3) 0.043(3) 0.034(2) 0.0004(19) -0.002(2) -0.001(2) C12 0.081(3) 0.059(3) 0.035(2) -0.002(2) -0.002(2) 0.002(2) C13 0.060(3) 0.064(3) 0.042(3) -0.018(2) -0.007(2) -0.001(2) C14 0.065(3) 0.045(3) 0.057(3) -0.011(2) -0.007(2) -0.008(2) C15 0.058(3) 0.041(3) 0.043(2) 0.000(2) -0.0060(19) -0.007(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 S1 C1 1.633(4) . ? O1 C1 1.367(4) . ? O1 C2 1.387(4) . ? C1 C8 1.455(5) . ? C2 C3 1.333(5) . ? C2 C10 1.469(5) . ? C3 C9 1.437(5) . ? C3 H3 1.043(18) . ? C4 C5 1.376(5) . ? C4 C9 1.397(5) . ? C4 H4 1.050(18) . ? C5 C6 1.383(6) . ? C5 H5 1.049(19) . ? C6 C7 1.377(5) . ? C6 H6 1.034(18) . ? C7 C8 1.403(5) . ? C7 H7 1.026(18) . ? C8 C9 1.397(5) . ? C10 C15 1.387(5) . ? C10 C11 1.388(5) . ? C11 C12 1.388(5) . ? C11 H11 1.047(19) . ? C12 C13 1.367(6) . ? C12 H12 1.051(19) . ? C13 C14 1.376(6) . ? C13 H13 1.039(19) . ? C14 C15 1.383(5) . ? C14 H14 1.042(19) . ? C15 H15 1.051(18) . ? 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 C8 116.4(3) . . ? O1 C2 C10 111.4(3) . . ? O1 C1 S1 116.3(2) . . ? C1 O1 C2 123.7(3) . . ? C2 C3 C9 120.8(3) . . ? C2 C3 H3 122.4(19) . . ? C3 C2 O1 120.2(3) . . ? C3 C2 C10 128.4(3) . . ? C4 C5 C6 120.3(4) . . ? C4 C5 H5 121(2) . . ? C4 C9 C8 119.5(3) . . ? C4 C9 C3 121.9(3) . . ? C5 C4 C9 120.2(4) . . ? C5 C4 H4 119(2) . . ? C5 C6 H6 124(2) . . ? C6 C7 C8 119.7(4) . . ? C6 C7 H7 120(2) . . ? C6 C5 H5 118(2) . . ? C7 C6 C5 120.6(4) . . ? C7 C6 H6 116(2) . . ? C7 C8 C1 120.2(3) . . ? C8 C1 S1 127.3(3) . . ? C8 C9 C3 118.6(3) . . ? C8 C7 H7 120(2) . . ? C9 C3 H3 116.8(19) . . ? C9 C4 H4 121(2) . . ? C9 C8 C7 119.6(3) . . ? C9 C8 C1 120.2(3) . . ? C10 C11 C12 120.7(4) . . ? C10 C15 H15 120(2) . . ? C10 C11 H11 117(2) . . ? C11 C10 C2 121.1(3) . . ? C11 C12 H12 114(2) . . ? C12 C13 C14 120.2(4) . . ? C12 C13 H13 122(2) . . ? C12 C11 H11 122(2) . . ? C13 C12 C11 119.8(4) . . ? C13 C14 C15 120.5(4) . . ? C13 C14 H14 119(2) . . ? C13 C12 H12 126(2) . . ? C14 C13 H13 118(2) . . ? C14 C15 C10 120.0(4) . . ? C14 C15 H15 120(2) . . ? C15 C14 H14 120(2) . . ? C15 C10 C11 118.8(3) . . ? C15 C10 C2 120.1(3) . . ? 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 S1 C1 C8 C9 -177.1(3) . . . . ? S1 C1 C8 C7 3.5(5) . . . . ? O1 C1 C8 C9 1.8(5) . . . . ? O1 C1 C8 C7 -177.6(3) . . . . ? O1 C2 C10 C15 158.5(3) . . . . ? O1 C2 C10 C11 -21.5(5) . . . . ? O1 C2 C3 C9 1.1(5) . . . . ? C1 C8 C9 C4 179.0(3) . . . . ? C1 O1 C2 C3 -0.4(5) . . . . ? C1 O1 C2 C10 178.7(3) . . . . ? C1 C8 C9 C3 -1.2(5) . . . . ? C2 C3 C9 C4 179.5(4) . . . . ? C2 C3 C9 C8 -0.3(5) . . . . ? C2 C10 C11 C12 -179.1(4) . . . . ? C2 O1 C1 C8 -1.0(5) . . . . ? C2 O1 C1 S1 178.0(2) . . . . ? C2 C10 C15 C14 179.8(4) . . . . ? C3 C2 C10 C15 -22.5(6) . . . . ? C3 C2 C10 C11 157.6(4) . . . . ? C4 C5 C6 C7 -0.6(7) . . . . ? C5 C6 C7 C8 -0.3(6) . . . . ? C5 C4 C9 C8 0.7(6) . . . . ? C5 C4 C9 C3 -179.1(4) . . . . ? C6 C7 C8 C9 1.4(6) . . . . ? C6 C7 C8 C1 -179.2(4) . . . . ? C7 C8 C9 C4 -1.6(5) . . . . ? C7 C8 C9 C3 178.2(3) . . . . ? C9 C4 C5 C6 0.4(6) . . . . ? C10 C2 C3 C9 -177.9(3) . . . . ? C10 C11 C12 C13 -1.3(7) . . . . ? C11 C12 C13 C14 1.0(7) . . . . ? C11 C10 C15 C14 -0.2(6) . . . . ? C12 C13 C14 C15 -0.4(7) . . . . ? C13 C14 C15 C10 0.0(6) . . . . ? C15 C10 C11 C12 0.9(6) . . . . ? #===END