# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Baruah, Jubaraj' _publ_contact_author_email juba@iitg.ernet.in _publ_section_title ; Polymorphs of naphthoquinones primarily guided by C-H ***O interactions ; loop_ _publ_author_name J.Baruah B.Jali M.Singh # Attachment 'dithiolatomethylnaphtho.cif' data_qtcre _database_code_depnum_ccdc_archive 'CCDC 662871' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 O2 S2' _chemical_formula_weight 402.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.7587(2) _cell_length_b 19.4871(8) _cell_length_c 31.0120(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4084.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour red _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.277 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20811 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0287 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5044 _reflns_number_gt 3088 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0851P)^2^+1.1144P] 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 0.78(12) _refine_ls_number_reflns 5044 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0944 _refine_ls_R_factor_gt 0.0555 _refine_ls_wR_factor_ref 0.1771 _refine_ls_wR_factor_gt 0.1529 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 S2 S 0.26717(19) 0.21286(4) 0.10279(2) 0.0839(3) Uani 1 1 d . . . S1 S 0.2694(2) 0.12934(6) 0.19575(4) 0.1120(4) Uani 1 1 d . . . C1 C 0.2289(7) 0.4392(2) 0.19369(13) 0.0910(11) Uani 1 1 d . . . H1 H 0.2161 0.4625 0.1677 0.109 Uiso 1 1 calc R . . C7 C 0.2521(6) 0.21822(17) 0.19089(9) 0.0765(9) Uani 1 1 d . . . C9 C 0.2071(5) 0.32973(17) 0.15316(10) 0.0696(9) Uani 1 1 d . . . C8 C 0.2474(6) 0.25375(15) 0.15327(8) 0.0659(8) Uani 1 1 d . . . C6 C 0.2499(6) 0.2570(2) 0.23328(10) 0.0845(11) Uani 1 1 d . . . C5 C 0.2476(6) 0.33260(19) 0.23231(10) 0.0778(9) Uani 1 1 d . . . C4 C 0.2616(7) 0.3695(3) 0.27158(12) 0.0992(13) Uani 1 1 d . . . H4 H 0.2688 0.3470 0.2980 0.119 Uiso 1 1 calc R . . C10 C 0.2286(5) 0.36785(18) 0.19375(10) 0.0721(8) Uani 1 1 d . . . C3 C 0.2642(9) 0.4395(3) 0.26914(16) 0.1161(16) Uani 1 1 d . . . H3 H 0.2780 0.4643 0.2946 0.139 Uiso 1 1 calc R . . C2 C 0.2474(10) 0.4756(2) 0.23086(16) 0.1191(17) Uani 1 1 d . . . H2 H 0.2487 0.5233 0.2306 0.143 Uiso 1 1 calc R . . O1 O 0.2602(6) 0.22432(18) 0.26657(8) 0.1243(12) Uani 1 1 d . . . O2 O 0.1540(4) 0.35905(13) 0.12083(8) 0.0885(8) Uani 1 1 d . . . C21 C 0.6747(6) 0.35224(16) 0.02383(10) 0.0707(9) Uani 1 1 d . . . C23 C 0.7344(6) 0.32610(18) 0.06346(11) 0.0806(9) Uani 1 1 d . . . H23 H 0.8605 0.3361 0.0737 0.097 Uiso 1 1 calc R . . C18 C 0.4228(6) 0.27043(16) 0.07352(9) 0.0676(8) Uani 1 1 d . . . C19 C 0.3608(5) 0.29509(16) 0.03430(9) 0.0669(8) Uani 1 1 d . . . H19 H 0.2347 0.2847 0.0242 0.080 Uiso 1 1 calc R . . C24 C 0.6103(6) 0.28573(19) 0.08779(10) 0.0807(10) Uani 1 1 d . . . H24 H 0.6537 0.2686 0.1141 0.097 Uiso 1 1 calc R . . C20 C 0.4862(6) 0.33545(16) 0.00976(10) 0.0701(9) Uani 1 1 d . . . H20 H 0.4429 0.3517 -0.0168 0.084 Uiso 1 1 calc R . . C22 C 0.8129(7) 0.3952(2) -0.00263(14) 0.1022(13) Uani 1 1 d . . . H22A H 0.7388 0.4199 -0.0240 0.153 Uiso 1 1 calc R . . H22B H 0.9079 0.3661 -0.0166 0.153 Uiso 1 1 calc R . . H22C H 0.8804 0.4272 0.0158 0.153 Uiso 1 1 calc R . . C16 C -0.0859(7) 0.12027(18) 0.15117(12) 0.0823(10) Uani 1 1 d . . . H16 H -0.1317 0.1558 0.1686 0.099 Uiso 1 1 calc R . . C15 C -0.2098(7) 0.09117(18) 0.12047(13) 0.0903(11) Uani 1 1 d . . . H15 H -0.3369 0.1086 0.1170 0.108 Uiso 1 1 calc R . . C13 C 0.0404(9) 0.01303(19) 0.10083(13) 0.0943(13) Uani 1 1 d . . . H13 H 0.0842 -0.0240 0.0845 0.113 Uiso 1 1 calc R . . C11 C 0.1071(7) 0.09625(18) 0.15588(12) 0.0802(10) Uani 1 1 d . . . C14 C -0.1494(8) 0.03699(18) 0.09486(12) 0.0867(12) Uani 1 1 d . . . C17 C -0.2864(10) 0.0050(2) 0.06217(15) 0.133(2) Uani 1 1 d . . . H17A H -0.2171 -0.0301 0.0466 0.200 Uiso 1 1 calc R . . H17B H -0.3315 0.0396 0.0424 0.200 Uiso 1 1 calc R . . H17C H -0.3980 -0.0148 0.0767 0.200 Uiso 1 1 calc R . . C12 C 0.1679(7) 0.0426(2) 0.13049(14) 0.0944(13) Uani 1 1 d . . . H12 H 0.2962 0.0259 0.1332 0.113 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S2 0.1362(9) 0.0597(4) 0.0559(4) -0.0029(3) 0.0087(5) -0.0215(6) S1 0.1464(11) 0.0868(7) 0.1028(7) 0.0391(6) -0.0358(8) -0.0197(8) C1 0.098(3) 0.082(2) 0.094(2) -0.0222(19) 0.007(3) -0.009(2) C7 0.085(2) 0.087(2) 0.0576(15) 0.0097(15) -0.0074(18) -0.017(2) C9 0.073(2) 0.074(2) 0.0622(17) -0.0074(15) 0.0022(16) -0.0144(17) C8 0.083(2) 0.0666(18) 0.0480(14) 0.0015(12) -0.0019(16) -0.0103(18) C6 0.073(2) 0.130(3) 0.0505(16) 0.0169(17) -0.0008(17) -0.020(2) C5 0.0623(19) 0.100(3) 0.0708(19) -0.0131(17) 0.0083(18) -0.014(2) C4 0.081(3) 0.149(4) 0.068(2) -0.021(2) 0.015(2) -0.018(3) C10 0.067(2) 0.081(2) 0.0678(17) -0.0094(16) 0.0087(17) -0.0106(19) C3 0.115(4) 0.136(4) 0.097(3) -0.059(3) 0.017(3) -0.017(4) C2 0.143(4) 0.108(3) 0.106(3) -0.043(3) 0.029(4) -0.007(4) O1 0.159(3) 0.157(3) 0.0568(13) 0.0296(15) -0.0074(17) -0.040(3) O2 0.123(2) 0.0719(14) 0.0709(14) 0.0005(12) -0.0164(14) 0.0029(14) C21 0.094(3) 0.0555(17) 0.0626(17) -0.0104(14) 0.0038(16) -0.0052(16) C23 0.085(2) 0.080(2) 0.076(2) -0.0059(17) -0.008(2) -0.009(2) C18 0.093(2) 0.0572(17) 0.0528(15) -0.0014(13) 0.0010(16) -0.0042(17) C19 0.083(2) 0.0609(17) 0.0570(16) -0.0010(14) -0.0074(15) -0.0032(17) C24 0.107(3) 0.077(2) 0.0580(17) 0.0046(16) -0.0184(18) -0.005(2) C20 0.101(3) 0.0568(18) 0.0519(15) 0.0026(13) -0.0034(16) 0.0011(18) C22 0.126(3) 0.092(3) 0.089(2) 0.001(2) 0.020(3) -0.029(3) C16 0.106(3) 0.0569(19) 0.084(2) -0.0032(17) 0.013(2) -0.002(2) C15 0.109(3) 0.063(2) 0.099(3) 0.0016(19) -0.003(2) -0.001(2) C13 0.149(4) 0.059(2) 0.075(2) 0.0039(18) 0.025(3) 0.008(3) C11 0.106(3) 0.0617(19) 0.073(2) 0.0161(17) 0.011(2) -0.002(2) C14 0.130(4) 0.0581(19) 0.072(2) 0.0037(16) 0.002(2) -0.001(2) C17 0.208(6) 0.089(3) 0.103(3) -0.009(3) -0.019(4) -0.018(4) C12 0.115(3) 0.071(2) 0.096(3) 0.030(2) 0.023(3) 0.013(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 S2 C8 1.762(3) . ? S2 C18 1.786(3) . ? S1 C7 1.742(4) . ? S1 C11 1.774(4) . ? C1 C2 1.360(6) . ? C1 C10 1.390(5) . ? C1 H1 0.9300 . ? C7 C8 1.357(4) . ? C7 C6 1.516(5) . ? C9 O2 1.209(4) . ? C9 C10 1.469(4) . ? C9 C8 1.506(5) . ? C6 O1 1.215(4) . ? C6 C5 1.474(5) . ? C5 C10 1.385(5) . ? C5 C4 1.418(5) . ? C4 C3 1.366(7) . ? C4 H4 0.9300 . ? C3 C2 1.385(6) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C21 C20 1.386(5) . ? C21 C23 1.390(5) . ? C21 C22 1.499(5) . ? C23 C24 1.375(5) . ? C23 H23 0.9300 . ? C18 C19 1.373(4) . ? C18 C24 1.375(5) . ? C19 C20 1.384(5) . ? C19 H19 0.9300 . ? C24 H24 0.9300 . ? C20 H20 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C16 C15 1.389(6) . ? C16 C11 1.393(6) . ? C16 H16 0.9300 . ? C15 C14 1.383(5) . ? C15 H15 0.9300 . ? C13 C14 1.378(6) . ? C13 C12 1.386(6) . ? C13 H13 0.9300 . ? C11 C12 1.372(5) . ? C14 C17 1.508(7) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 S2 C18 102.25(15) . . ? C7 S1 C11 105.04(17) . . ? C2 C1 C10 121.4(4) . . ? C2 C1 H1 119.3 . . ? C10 C1 H1 119.3 . . ? C8 C7 C6 119.4(3) . . ? C8 C7 S1 125.7(3) . . ? C6 C7 S1 114.9(2) . . ? O2 C9 C10 120.1(3) . . ? O2 C9 C8 121.4(3) . . ? C10 C9 C8 118.5(3) . . ? C7 C8 C9 120.5(3) . . ? C7 C8 S2 122.1(3) . . ? C9 C8 S2 117.2(2) . . ? O1 C6 C5 122.8(3) . . ? O1 C6 C7 118.4(4) . . ? C5 C6 C7 118.7(3) . . ? C10 C5 C4 119.7(4) . . ? C10 C5 C6 121.0(3) . . ? C4 C5 C6 119.3(3) . . ? C3 C4 C5 117.4(4) . . ? C3 C4 H4 121.3 . . ? C5 C4 H4 121.3 . . ? C5 C10 C1 119.8(3) . . ? C5 C10 C9 119.9(3) . . ? C1 C10 C9 120.3(3) . . ? C4 C3 C2 123.6(4) . . ? C4 C3 H3 118.2 . . ? C2 C3 H3 118.2 . . ? C1 C2 C3 118.0(4) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C20 C21 C23 117.3(3) . . ? C20 C21 C22 122.2(3) . . ? C23 C21 C22 120.5(4) . . ? C24 C23 C21 121.2(4) . . ? C24 C23 H23 119.4 . . ? C21 C23 H23 119.4 . . ? C19 C18 C24 119.4(3) . . ? C19 C18 S2 119.3(3) . . ? C24 C18 S2 121.0(3) . . ? C18 C19 C20 119.9(3) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C23 C24 C18 120.6(3) . . ? C23 C24 H24 119.7 . . ? C18 C24 H24 119.7 . . ? C19 C20 C21 121.6(3) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C15 C16 C11 119.9(4) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C14 C15 C16 121.8(4) . . ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 . . ? C14 C13 C12 121.8(4) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C12 C11 C16 118.5(4) . . ? C12 C11 S1 119.4(4) . . ? C16 C11 S1 122.0(3) . . ? C13 C14 C15 117.1(4) . . ? C13 C14 C17 121.5(4) . . ? C15 C14 C17 121.4(5) . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C11 C12 C13 120.8(4) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 S1 C7 C8 -42.4(4) . . . . ? C11 S1 C7 C6 139.9(3) . . . . ? C6 C7 C8 C9 -9.9(6) . . . . ? S1 C7 C8 C9 172.4(3) . . . . ? C6 C7 C8 S2 175.4(3) . . . . ? S1 C7 C8 S2 -2.2(5) . . . . ? O2 C9 C8 C7 -161.4(4) . . . . ? C10 C9 C8 C7 17.0(6) . . . . ? O2 C9 C8 S2 13.5(5) . . . . ? C10 C9 C8 S2 -168.1(3) . . . . ? C18 S2 C8 C7 -139.7(3) . . . . ? C18 S2 C8 C9 45.5(3) . . . . ? C8 C7 C6 O1 -177.8(4) . . . . ? S1 C7 C6 O1 0.1(5) . . . . ? C8 C7 C6 C5 -1.5(6) . . . . ? S1 C7 C6 C5 176.4(3) . . . . ? O1 C6 C5 C10 -177.7(4) . . . . ? C7 C6 C5 C10 6.2(6) . . . . ? O1 C6 C5 C4 1.2(7) . . . . ? C7 C6 C5 C4 -174.9(3) . . . . ? C10 C5 C4 C3 -2.8(7) . . . . ? C6 C5 C4 C3 178.3(5) . . . . ? C4 C5 C10 C1 1.7(7) . . . . ? C6 C5 C10 C1 -179.4(4) . . . . ? C4 C5 C10 C9 -177.9(4) . . . . ? C6 C5 C10 C9 1.0(6) . . . . ? C2 C1 C10 C5 0.0(8) . . . . ? C2 C1 C10 C9 179.6(4) . . . . ? O2 C9 C10 C5 166.2(4) . . . . ? C8 C9 C10 C5 -12.3(6) . . . . ? O2 C9 C10 C1 -13.5(6) . . . . ? C8 C9 C10 C1 168.1(4) . . . . ? C5 C4 C3 C2 2.2(9) . . . . ? C10 C1 C2 C3 -0.6(9) . . . . ? C4 C3 C2 C1 -0.5(10) . . . . ? C20 C21 C23 C24 -0.6(5) . . . . ? C22 C21 C23 C24 -179.0(4) . . . . ? C8 S2 C18 C19 -126.1(3) . . . . ? C8 S2 C18 C24 59.6(3) . . . . ? C24 C18 C19 C20 -0.6(5) . . . . ? S2 C18 C19 C20 -175.0(2) . . . . ? C21 C23 C24 C18 -0.3(5) . . . . ? C19 C18 C24 C23 0.9(5) . . . . ? S2 C18 C24 C23 175.2(3) . . . . ? C18 C19 C20 C21 -0.3(5) . . . . ? C23 C21 C20 C19 0.9(5) . . . . ? C22 C21 C20 C19 179.3(3) . . . . ? C11 C16 C15 C14 2.0(6) . . . . ? C15 C16 C11 C12 -1.8(5) . . . . ? C15 C16 C11 S1 -177.8(3) . . . . ? C7 S1 C11 C12 135.6(3) . . . . ? C7 S1 C11 C16 -48.5(3) . . . . ? C12 C13 C14 C15 -1.4(6) . . . . ? C12 C13 C14 C17 179.3(4) . . . . ? C16 C15 C14 C13 -0.4(5) . . . . ? C16 C15 C14 C17 178.9(4) . . . . ? C16 C11 C12 C13 0.1(5) . . . . ? S1 C11 C12 C13 176.2(3) . . . . ? C14 C13 C12 C11 1.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.275 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.048 data_m1 _database_code_depnum_ccdc_archive 'CCDC 699026' #TrackingRef 'm1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H18 O2 S2' _chemical_formula_weight 402.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 16.3268(5) _cell_length_b 22.0140(8) _cell_length_c 5.34810(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1922.20(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2847 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description blocks _exptl_crystal_colour red _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.295 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24597 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2424 _reflns_number_gt 1043 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One sulphur was disordered. It was approximated by two oreintation, (i) S (1) (ii) S(1)', having occupancies of 1/2 The atoms are refine anisotropically. ; _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^)+(0.1353P)^2^+0.4267P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2424 _refine_ls_number_parameters 138 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.1780 _refine_ls_R_factor_gt 0.0807 _refine_ls_wR_factor_ref 0.2911 _refine_ls_wR_factor_gt 0.2293 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.7617(5) 0.6934(3) 1.2204(13) 0.110(2) Uani 0.50 1 d P . 1 S1' S 0.7500(6) 0.6663(3) 1.2085(13) 0.120(2) Uani 0.50 1 d P . 2 C6 C 0.8035(2) 0.6208(2) 1.0503(8) 0.1052(13) Uani 1 1 d . . . C12 C 0.8492(3) 0.6320(2) 0.8371(8) 0.1065(13) Uani 1 1 d . . . H12 H 0.8511 0.6707 0.7681 0.128 Uiso 1 1 calc R . . C11 C 0.8907(3) 0.5859(3) 0.7311(9) 0.1238(16) Uani 1 1 d . . . H11 H 0.9213 0.5925 0.5870 0.149 Uiso 1 1 calc R . . C9 C 0.8879(4) 0.5285(3) 0.8373(16) 0.147(2) Uani 1 1 d . . . C8 C 0.8426(5) 0.5210(4) 1.0502(15) 0.156(2) Uani 1 1 d U . . H8 H 0.8414 0.4828 1.1242 0.187 Uiso 1 1 calc R . . C7 C 0.8019(4) 0.5639(3) 1.1524(14) 0.146(2) Uani 1 1 d U . . H7 H 0.7712 0.5565 1.2957 0.175 Uiso 1 1 calc R . . C5 C 0.6993(2) 0.71980(18) 0.9888(7) 0.1025(14) Uani 1 1 d . . . C3 C 0.5930(2) 0.71917(16) 0.6417(7) 0.0836(10) Uani 1 1 d . . . C1 C 0.4972(3) 0.7192(2) 0.3025(9) 0.1137(15) Uani 1 1 d . . . H1 H 0.4648 0.6981 0.1892 0.136 Uiso 1 1 calc R . . C2 C 0.5448(2) 0.6883(2) 0.4689(8) 0.1036(13) Uani 1 1 d . . . H2 H 0.5450 0.6461 0.4667 0.124 Uiso 1 1 calc R . . C4 C 0.6426(2) 0.6852(2) 0.8247(8) 0.0986(12) Uani 1 1 d . . . O1 O 0.6366(2) 0.63052(17) 0.8454(7) 0.1349(13) Uani 1 1 d . . . C10 C 0.9310(8) 0.4816(6) 0.728(2) 0.303(6) Uani 1 1 d . . . H10B H 0.9253 0.4456 0.8281 0.455 Uiso 1 1 calc R . . H10A H 0.9879 0.4924 0.7174 0.455 Uiso 1 1 calc R . . H10C H 0.9099 0.4741 0.5636 0.455 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.099(2) 0.153(6) 0.0797(17) -0.020(3) -0.0095(14) 0.028(3) S1' 0.149(5) 0.138(5) 0.074(2) 0.011(3) -0.004(2) 0.044(4) C6 0.075(2) 0.147(4) 0.093(3) 0.024(3) -0.012(2) 0.000(2) C12 0.105(3) 0.114(3) 0.100(3) 0.012(2) -0.001(2) 0.001(3) C11 0.116(4) 0.140(5) 0.115(3) -0.020(3) -0.003(3) 0.013(3) C9 0.126(4) 0.112(4) 0.203(6) -0.051(5) -0.071(4) 0.036(4) C8 0.144(5) 0.156(5) 0.168(5) 0.047(4) -0.046(4) -0.025(3) C7 0.121(4) 0.161(5) 0.156(5) 0.055(4) -0.036(4) -0.020(3) C5 0.075(2) 0.158(4) 0.074(2) 0.008(2) 0.0056(18) 0.011(2) C3 0.0608(19) 0.108(2) 0.082(2) -0.0002(17) 0.0093(16) -0.0039(17) C1 0.076(2) 0.156(4) 0.110(3) -0.006(2) -0.009(2) -0.006(2) C2 0.084(3) 0.116(3) 0.111(3) -0.003(3) 0.010(2) -0.007(2) C4 0.082(3) 0.114(3) 0.100(3) 0.008(2) 0.014(2) 0.006(2) O1 0.122(3) 0.127(3) 0.156(3) 0.027(2) -0.013(2) 0.004(2) C10 0.302(13) 0.263(11) 0.344(15) -0.075(10) -0.132(11) 0.041(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C5 1.706(8) . ? S1 C6 1.961(7) . ? S1 S1 2.493(12) 7_575 ? S1' C6 1.576(9) . ? S1' C5 1.858(8) . ? C6 C7 1.367(7) . ? C6 C12 1.384(6) . ? C12 C11 1.345(6) . ? C11 C9 1.386(8) . ? C9 C8 1.367(9) . ? C9 C10 1.380(11) . ? C8 C7 1.279(9) . ? C5 C5 1.330(8) 7_575 ? C5 C4 1.486(6) . ? C3 C3 1.357(7) 7_575 ? C3 C2 1.391(5) . ? C3 C4 1.474(6) . ? C1 C1 1.354(11) 7_575 ? C1 C2 1.363(6) . ? C4 O1 1.212(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 S1 C6 98.6(3) . . ? C5 S1 S1 70.1(2) . 7_575 ? C6 S1 S1 144.5(2) . 7_575 ? C6 S1' C5 108.1(4) . . ? C7 C6 C12 120.1(5) . . ? C7 C6 S1' 110.9(5) . . ? C12 C6 S1' 129.0(5) . . ? C7 C6 S1 123.7(5) . . ? C12 C6 S1 115.2(4) . . ? S1' C6 S1 16.3(4) . . ? C11 C12 C6 119.0(4) . . ? C12 C11 C9 119.8(5) . . ? C8 C9 C10 122.5(10) . . ? C8 C9 C11 118.0(6) . . ? C10 C9 C11 119.5(9) . . ? C7 C8 C9 123.2(8) . . ? C8 C7 C6 119.8(7) . . ? C5 C5 C4 120.9(2) 7_575 . ? C5 C5 S1 109.9(2) 7_575 . ? C4 C5 S1 128.7(4) . . ? C5 C5 S1' 129.3(2) 7_575 . ? C4 C5 S1' 109.0(4) . . ? S1 C5 S1' 19.7(3) . . ? C3 C3 C2 119.2(2) 7_575 . ? C3 C3 C4 120.5(2) 7_575 . ? C2 C3 C4 120.2(4) . . ? C1 C1 C2 119.9(3) 7_575 . ? C1 C2 C3 120.8(4) . . ? O1 C4 C3 121.4(4) . . ? O1 C4 C5 120.3(4) . . ? C3 C4 C5 118.3(4) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.152 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.042 # Attachment 'NQTh_0m.cif' data_nqth_0m _database_code_depnum_ccdc_archive 'CCDC 789552' #TrackingRef 'NQTh_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 O2 S' _chemical_formula_weight 266.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.5694(4) _cell_length_b 23.812(2) _cell_length_c 11.7744(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.299(6) _cell_angle_gamma 90.00 _cell_volume 1264.31(19) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 878 _cell_measurement_theta_min 4.52 _cell_measurement_theta_max 20.80 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9095 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0551 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.60 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2252 _reflns_number_gt 1457 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2252 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0887 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1661 _refine_ls_wR_factor_gt 0.1389 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 0.1473(7) 0.75097(13) 0.3919(3) 0.0700(9) Uani 1 1 d . . . H1 H 0.2088 0.7855 0.3672 0.084 Uiso 1 1 calc R . . C2 C -0.0141(7) 0.74926(15) 0.4806(3) 0.0740(10) Uani 1 1 d . . . H2 H -0.0611 0.7823 0.5157 0.089 Uiso 1 1 calc R . . C3 C -0.1060(7) 0.69831(16) 0.5172(3) 0.0743(10) Uani 1 1 d . . . H3 H -0.2136 0.6969 0.5778 0.089 Uiso 1 1 calc R . . C4 C -0.0393(6) 0.64922(14) 0.4645(3) 0.0634(8) Uani 1 1 d . . . H4 H -0.1046 0.6151 0.4898 0.076 Uiso 1 1 calc R . . C5 C 0.1239(5) 0.64966(11) 0.3741(2) 0.0497(7) Uani 1 1 d . . . C6 C 0.2207(6) 0.70203(12) 0.3384(2) 0.0540(7) Uani 1 1 d . . . C7 C 0.4023(6) 0.70496(13) 0.2453(3) 0.0602(8) Uani 1 1 d . . . C8 C 0.4718(6) 0.64965(13) 0.1889(3) 0.0618(8) Uani 1 1 d . . . C9 C 0.3571(6) 0.59868(12) 0.2286(2) 0.0560(7) Uani 1 1 d . . . H9 H 0.3941 0.5650 0.1935 0.067 Uiso 1 1 calc R . . C10 C 0.1961(5) 0.59794(11) 0.3156(2) 0.0482(6) Uani 1 1 d . . . C11 C 0.1638(7) 0.48157(12) 0.2820(3) 0.0605(8) Uani 1 1 d . . . C12 C 0.3786(7) 0.44365(13) 0.3309(3) 0.0670(8) Uani 1 1 d . . . H12 H 0.4772 0.4492 0.4056 0.080 Uiso 1 1 calc R . . C13 C 0.4453(8) 0.39771(15) 0.2684(4) 0.0831(10) Uani 1 1 d . . . H13 H 0.5862 0.3719 0.3016 0.100 Uiso 1 1 calc R . . C14 C 0.3057(9) 0.39002(16) 0.1579(4) 0.0851(11) Uani 1 1 d . . . H14 H 0.3529 0.3591 0.1160 0.102 Uiso 1 1 calc R . . C15 C 0.0980(9) 0.42735(18) 0.1091(3) 0.0873(11) Uani 1 1 d . . . H15 H 0.0057 0.4221 0.0335 0.105 Uiso 1 1 calc R . . C16 C 0.0221(8) 0.47317(16) 0.1709(3) 0.0804(10) Uani 1 1 d . . . H16 H -0.1237 0.4981 0.1376 0.096 Uiso 1 1 calc R . . O1 O 0.4993(6) 0.74865(10) 0.2144(2) 0.0862(7) Uani 1 1 d . . . O2 O 0.6241(6) 0.65068(11) 0.1115(2) 0.0950(8) Uani 1 1 d . . . S1 S 0.05725(19) 0.53637(3) 0.36881(7) 0.0691(3) 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 0.0777(18) 0.0473(19) 0.083(2) -0.0070(16) 0.0083(17) 0.0005(14) C2 0.0772(18) 0.059(2) 0.083(2) -0.0234(18) 0.0041(18) 0.0139(16) C3 0.0765(19) 0.079(3) 0.070(2) -0.0198(18) 0.0207(17) 0.0086(17) C4 0.0726(17) 0.061(2) 0.0620(19) -0.0044(15) 0.0259(15) 0.0010(14) C5 0.0525(13) 0.0444(17) 0.0527(17) -0.0013(12) 0.0100(12) 0.0031(11) C6 0.0608(15) 0.0426(17) 0.0573(17) 0.0011(13) 0.0052(13) -0.0005(12) C7 0.0674(16) 0.055(2) 0.0583(18) 0.0068(15) 0.0084(14) -0.0053(13) C8 0.0708(17) 0.065(2) 0.0528(18) 0.0053(14) 0.0190(14) -0.0060(14) C9 0.0693(16) 0.0470(17) 0.0551(18) -0.0025(13) 0.0198(13) 0.0011(13) C10 0.0560(13) 0.0416(16) 0.0488(16) 0.0041(12) 0.0140(12) 0.0016(11) C11 0.0772(18) 0.0403(17) 0.068(2) 0.0018(14) 0.0223(16) -0.0054(13) C12 0.088(2) 0.0453(18) 0.069(2) 0.0040(15) 0.0157(16) -0.0044(15) C13 0.099(2) 0.053(2) 0.099(3) 0.000(2) 0.020(2) 0.0090(17) C14 0.110(3) 0.050(2) 0.099(3) -0.019(2) 0.029(2) -0.0062(19) C15 0.110(3) 0.083(3) 0.070(2) -0.018(2) 0.016(2) -0.013(2) C16 0.091(2) 0.073(3) 0.075(3) -0.0034(19) 0.0057(19) 0.0071(17) O1 0.1163(17) 0.0579(16) 0.0883(18) 0.0138(12) 0.0277(13) -0.0214(13) O2 0.1291(19) 0.0887(19) 0.0822(17) 0.0031(13) 0.0625(15) -0.0170(15) S1 0.0993(6) 0.0445(5) 0.0727(6) 0.0032(4) 0.0413(5) -0.0044(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.373(5) . ? C1 C6 1.392(4) . ? C2 C3 1.376(5) . ? C3 C4 1.380(4) . ? C4 C5 1.395(4) . ? C5 C6 1.410(4) . ? C5 C10 1.474(4) . ? C6 C7 1.479(4) . ? C7 O1 1.210(3) . ? C7 C8 1.531(4) . ? C8 O2 1.232(3) . ? C8 C9 1.430(4) . ? C9 C10 1.355(4) . ? C10 S1 1.753(3) . ? C11 C16 1.377(5) . ? C11 C12 1.388(4) . ? C11 S1 1.773(3) . ? C12 C13 1.380(5) . ? C13 C14 1.365(5) . ? C14 C15 1.358(6) . ? C15 C16 1.386(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.2(3) . . ? C1 C2 C3 119.6(3) . . ? C2 C3 C4 120.3(3) . . ? C3 C4 C5 121.4(3) . . ? C4 C5 C6 117.8(3) . . ? C4 C5 C10 122.5(3) . . ? C6 C5 C10 119.6(2) . . ? C1 C6 C5 119.7(3) . . ? C1 C6 C7 120.1(3) . . ? C5 C6 C7 120.2(2) . . ? O1 C7 C6 122.7(3) . . ? O1 C7 C8 119.8(3) . . ? C6 C7 C8 117.5(2) . . ? O2 C8 C9 122.6(3) . . ? O2 C8 C7 119.0(3) . . ? C9 C8 C7 118.4(2) . . ? C10 C9 C8 122.0(3) . . ? C9 C10 C5 122.2(2) . . ? C9 C10 S1 123.6(2) . . ? C5 C10 S1 114.22(18) . . ? C16 C11 C12 119.4(3) . . ? C16 C11 S1 121.6(2) . . ? C12 C11 S1 118.8(3) . . ? C13 C12 C11 119.8(3) . . ? C14 C13 C12 120.3(3) . . ? C15 C14 C13 120.1(3) . . ? C14 C15 C16 120.7(4) . . ? C11 C16 C15 119.6(3) . . ? C10 S1 C11 105.10(13) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.214 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.037 # Attachment 'bgy.cif' data_bgy _database_code_depnum_ccdc_archive 'CCDC 789553' #TrackingRef 'bgy.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H10 O2 S' _chemical_formula_weight 266.30 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7573(9) _cell_length_b 8.3355(8) _cell_length_c 10.1969(11) _cell_angle_alpha 75.158(7) _cell_angle_beta 89.963(7) _cell_angle_gamma 86.091(7) _cell_volume 635.76(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4099 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7501 _diffrn_reflns_av_R_equivalents 0.0743 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2279 _reflns_number_gt 1879 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2279 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1467 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 -0.3127(2) 0.1578(2) 0.49668(19) 0.0470(5) Uani 1 1 d . . . H1 H -0.3814 0.0721 0.5371 0.056 Uiso 1 1 calc R . . C2 C -0.3391(2) 0.3103(2) 0.5256(2) 0.0520(5) Uani 1 1 d . . . H2 H -0.4249 0.3273 0.5853 0.062 Uiso 1 1 calc R . . C3 C -0.2375(2) 0.4375(2) 0.4654(2) 0.0500(5) Uani 1 1 d . . . H3 H -0.2556 0.5406 0.4845 0.060 Uiso 1 1 calc R . . C4 C -0.1092(2) 0.4134(2) 0.37710(19) 0.0436(4) Uani 1 1 d . . . H4 H -0.0419 0.5005 0.3372 0.052 Uiso 1 1 calc R . . C5 C -0.0795(2) 0.25948(19) 0.34694(16) 0.0357(4) Uani 1 1 d . . . C6 C -0.1849(2) 0.1309(2) 0.40795(17) 0.0385(4) Uani 1 1 d . . . C7 C -0.1651(2) -0.0318(2) 0.37419(19) 0.0445(5) Uani 1 1 d . . . C8 C -0.0216(2) -0.0562(2) 0.2760(2) 0.0457(5) Uani 1 1 d . . . C9 C 0.0833(2) 0.0800(2) 0.22321(19) 0.0449(5) Uani 1 1 d . . . H9 H 0.1725 0.0659 0.1653 0.054 Uiso 1 1 calc R . . C10 C 0.0581(2) 0.2284(2) 0.25410(17) 0.0384(4) Uani 1 1 d . . . C11 C 0.3327(2) 0.3241(2) 0.08408(18) 0.0420(4) Uani 1 1 d . . . C12 C 0.2822(2) 0.3089(2) -0.0420(2) 0.0523(5) Uani 1 1 d . . . H12 H 0.1669 0.3312 -0.0699 0.063 Uiso 1 1 calc R . . C13 C 0.4023(3) 0.2608(3) -0.1259(2) 0.0591(5) Uani 1 1 d . . . H13 H 0.3683 0.2490 -0.2101 0.071 Uiso 1 1 calc R . . C14 C 0.5736(3) 0.2301(3) -0.0849(2) 0.0631(6) Uani 1 1 d . . . H14 H 0.6553 0.1991 -0.1422 0.076 Uiso 1 1 calc R . . C15 C 0.6235(3) 0.2451(3) 0.0400(2) 0.0650(6) Uani 1 1 d . . . H15 H 0.7390 0.2239 0.0672 0.078 Uiso 1 1 calc R . . C16 C 0.5031(2) 0.2916(2) 0.1257(2) 0.0551(5) Uani 1 1 d . . . H16 H 0.5370 0.3008 0.2108 0.066 Uiso 1 1 calc R . . O1 O -0.25896(18) -0.14330(17) 0.41880(16) 0.0645(4) Uani 1 1 d . . . O2 O -0.00200(18) -0.18996(16) 0.24717(16) 0.0647(4) Uani 1 1 d . . . S1 S 0.18249(6) 0.39835(5) 0.19017(5) 0.0526(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0426(10) 0.0479(11) 0.0484(11) -0.0071(8) 0.0024(8) -0.0091(8) C2 0.0453(10) 0.0596(12) 0.0513(11) -0.0158(9) 0.0087(8) 0.0010(9) C3 0.0531(11) 0.0422(10) 0.0564(12) -0.0173(8) 0.0032(9) 0.0031(8) C4 0.0475(10) 0.0350(10) 0.0491(10) -0.0113(7) 0.0045(8) -0.0056(8) C5 0.0358(9) 0.0337(9) 0.0367(9) -0.0069(7) -0.0022(7) -0.0040(7) C6 0.0361(9) 0.0373(9) 0.0405(9) -0.0066(7) -0.0037(7) -0.0051(7) C7 0.0451(10) 0.0375(10) 0.0497(11) -0.0075(8) -0.0060(8) -0.0091(8) C8 0.0471(10) 0.0341(10) 0.0571(11) -0.0142(8) -0.0034(8) -0.0019(8) C9 0.0439(10) 0.0384(10) 0.0544(11) -0.0157(8) 0.0074(8) -0.0018(8) C10 0.0410(9) 0.0339(9) 0.0405(9) -0.0094(7) 0.0004(7) -0.0045(7) C11 0.0445(10) 0.0375(9) 0.0430(10) -0.0070(7) 0.0068(8) -0.0089(7) C12 0.0451(10) 0.0597(12) 0.0511(11) -0.0115(9) 0.0020(8) -0.0079(9) C13 0.0678(13) 0.0653(13) 0.0485(11) -0.0202(9) 0.0108(10) -0.0122(10) C14 0.0658(13) 0.0554(13) 0.0667(14) -0.0153(10) 0.0228(11) 0.0031(10) C15 0.0450(11) 0.0721(15) 0.0709(15) -0.0078(11) 0.0018(10) 0.0053(10) C16 0.0544(12) 0.0615(13) 0.0476(11) -0.0099(9) -0.0019(9) -0.0067(10) O1 0.0669(9) 0.0457(8) 0.0840(11) -0.0162(7) 0.0175(8) -0.0265(7) O2 0.0693(10) 0.0405(8) 0.0924(11) -0.0303(7) 0.0090(8) -0.0092(7) S1 0.0605(4) 0.0408(3) 0.0610(4) -0.0176(2) 0.0238(3) -0.0171(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.378(3) . ? C1 C6 1.387(2) . ? C2 C3 1.380(3) . ? C3 C4 1.380(2) . ? C4 C5 1.399(2) . ? C5 C6 1.408(2) . ? C5 C10 1.480(2) . ? C6 C7 1.481(2) . ? C7 O1 1.215(2) . ? C7 C8 1.534(3) . ? C8 O2 1.224(2) . ? C8 C9 1.433(2) . ? C9 C10 1.354(2) . ? C10 S1 1.7537(16) . ? C11 C16 1.376(2) . ? C11 C12 1.384(3) . ? C11 S1 1.7760(18) . ? C12 C13 1.372(3) . ? C13 C14 1.380(3) . ? C14 C15 1.370(3) . ? C15 C16 1.382(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 C2 C1 C6 120.71(16) . . ? C1 C2 C3 119.64(17) . . ? C2 C3 C4 120.64(17) . . ? C3 C4 C5 120.71(16) . . ? C4 C5 C6 118.17(15) . . ? C4 C5 C10 122.25(14) . . ? C6 C5 C10 119.58(15) . . ? C1 C6 C5 120.11(16) . . ? C1 C6 C7 119.40(15) . . ? C5 C6 C7 120.45(16) . . ? O1 C7 C6 122.76(17) . . ? O1 C7 C8 119.65(17) . . ? C6 C7 C8 117.58(15) . . ? O2 C8 C9 123.42(17) . . ? O2 C8 C7 118.80(16) . . ? C9 C8 C7 117.79(15) . . ? C10 C9 C8 122.76(16) . . ? C9 C10 C5 121.76(15) . . ? C9 C10 S1 124.03(14) . . ? C5 C10 S1 114.21(12) . . ? C16 C11 C12 120.28(17) . . ? C16 C11 S1 118.84(14) . . ? C12 C11 S1 120.76(14) . . ? C13 C12 C11 119.91(18) . . ? C12 C13 C14 119.9(2) . . ? C15 C14 C13 120.19(19) . . ? C14 C15 C16 120.3(2) . . ? C11 C16 C15 119.42(19) . . ? C10 S1 C11 103.64(8) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.233 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.045