############################################################################## ### ### ### Electronic paper (Acta Crystallographica Section E) ### ### ### ############################################################################## # # # This CIF contains the data in a paper accepted for publication in Acta # # Crystallographica Section E. It conforms to the requirements of Notes # # for Authors for Section E, and has been peer reviewed under the auspices # # of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1. # # # # Software is freely available for graphical display of the structure(s) in # # this CIF. For information consult the CIF home page http://www.iucr.org/ # # cif/home.html # # # ############################################################################## data_global _audit_creation_method '?' _journal_date_recd_electronic 2008-01-07 _journal_date_accepted 2008-01-24 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2008 _journal_volume 64 _journal_issue 2 _journal_page_first o534 _journal_page_last o534 _journal_paper_category QO _journal_coeditor_code HG2371 _publ_contact_author_name 'Lan-Cui Zhang' _publ_contact_author_address ; College of Chemistry and Chemical Engineering Liaoning Normal University Dalian 116029 People's Republic of China ; _publ_contact_author_email zhanglc_07@sina.com _publ_contact_author_fax '86(411)82156318' _publ_contact_author_phone '86(411)82159312' _publ_section_title ; 2-(1,3-Dithian-2-ylidene)-1-phenylbutane-1,3-dione ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Lan-cui Zhang' ? ;College of Chemistry and Chemical Engineering Liaoning Normal University Dalian 116029 People's Republic of China ; 'Na Li' ? ;College of Chemistry and Chemical Engineering Liaoning Normal University Dalian 116029 People's Republic of China ; 'Xiao-Hui Li' ? ;College of Chemistry and Chemical Engineering Liaoning Normal University Dalian 116029 People's Republic of China ; 'Cui-ying Huang' ? ;College of Chemistry and Chemical Engineering Liaoning Normal University Dalian 116029 People's Republic of China ; 'Guang-hua Zhou' ? ;College of Chemistry and Chemical Engineering Liaoning Normal University Dalian 116029 People's Republic of China ; data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(1,3-Dithian-2-ylidene)-1-phenylbutane-1,3-dione ; _chemical_name_common ? _chemical_formula_moiety 'C13 H12 O2 S2' _chemical_formula_sum 'C13 H12 O2 S2' _chemical_formula_iupac 'C13 H12 O2 S2' _chemical_formula_weight 264.35 _chemical_melting_point ? _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.812(3) _cell_length_b 5.5115(18) _cell_length_c 14.628(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.876(4) _cell_angle_gamma 90.00 _cell_volume 611.4(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3425 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 27.83 _cell_measurement_temperature 298(2) _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2003)' _exptl_absorpt_correction_T_min 0.9564 _exptl_absorpt_correction_T_max 0.9933 _exptl_special_details ; ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3073 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _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. ; _reflns_number_total 1948 _reflns_number_gt 1887 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_gt 0.0718 _refine_ls_wR_factor_ref 0.0733 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_number_reflns 1948 _refine_ls_number_parameters 154 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment constr _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.1246P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.242 _refine_diff_density_min -0.165 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -0.01(8) 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' 'N' 'N' 0.0061 0.0033 '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' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_cell_refinement 'SAINT (Bruker, 2005)' _computing_data_reduction 'SAINT (Bruker, 2005)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008)' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S S1 0.45599(7) 0.16653(13) 0.16380(4) 0.04320(18) Uani d . 1 . . S S2 0.11323(8) 0.39993(14) 0.08953(4) 0.04637(18) Uani d . 1 . . O O1 0.4104(2) -0.2094(4) 0.27828(13) 0.0563(5) Uani d . 1 . . O O2 -0.1208(2) 0.2157(4) 0.17817(13) 0.0531(5) Uani d . 1 . . C C1 0.2829(3) -0.1090(5) 0.29623(15) 0.0361(5) Uani d . 1 . . C C2 0.1629(3) 0.0454(5) 0.22544(15) 0.0342(5) Uani d . 1 . . C C3 -0.0288(3) 0.0456(5) 0.21677(16) 0.0377(6) Uani d . 1 . . C C4 -0.1148(3) -0.1726(6) 0.24704(18) 0.0482(7) Uani d . 1 . . H H4A -0.2388 -0.1430 0.2380 0.072 Uiso calc R 1 . . H H4B -0.0636 -0.2046 0.3124 0.072 Uiso calc R 1 . . H H4C -0.0971 -0.3102 0.2101 0.072 Uiso calc R 1 . . C C5 0.2343(3) 0.1860(5) 0.16689(14) 0.0348(5) Uani d . 1 . . C C6 0.4601(4) 0.4458(6) 0.1000(2) 0.0532(7) Uani d . 1 . . H H6A 0.4788 0.5824 0.1431 0.064 Uiso calc R 1 . . H H6B 0.5552 0.4423 0.0679 0.064 Uiso calc R 1 . . C C7 0.2864(4) 0.4705(7) 0.0300(2) 0.0614(9) Uani d . 1 . . H H7A 0.2807 0.3597 -0.0222 0.074 Uiso calc R 1 . . H H7B 0.2720 0.6346 0.0055 0.074 Uiso calc R 1 . . C C8 0.2575(3) -0.1219(5) 0.39431(15) 0.0328(5) Uani d . 1 . . C C9 0.3325(3) -0.3133(5) 0.45259(16) 0.0390(5) Uani d . 1 . . H H9A 0.3892 -0.4378 0.4286 0.047 Uiso calc R 1 . . C C10 0.3233(3) -0.3194(6) 0.54551(17) 0.0459(6) Uani d . 1 . . H H10A 0.3714 -0.4495 0.5836 0.055 Uiso calc R 1 . . C C11 0.2424(3) -0.1316(6) 0.58230(17) 0.0461(7) Uani d . 1 . . H H11A 0.2390 -0.1337 0.6454 0.055 Uiso calc R 1 . . C C12 0.1671(3) 0.0579(6) 0.52532(17) 0.0438(6) Uani d . 1 . . H H12A 0.1111 0.1825 0.5497 0.053 Uiso calc R 1 . . C C13 0.1749(3) 0.0631(5) 0.43144(16) 0.0368(5) Uani d . 1 . . H H13A 0.1243 0.1917 0.3932 0.044 Uiso calc R 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0350(3) 0.0536(4) 0.0445(3) 0.0025(3) 0.0165(2) 0.0021(3) S2 0.0403(3) 0.0550(4) 0.0434(3) 0.0041(3) 0.0093(3) 0.0130(3) O1 0.0513(11) 0.0737(14) 0.0483(10) 0.0252(10) 0.0205(8) 0.0065(10) O2 0.0350(9) 0.0578(14) 0.0650(12) 0.0054(9) 0.0091(8) 0.0119(10) C1 0.0330(11) 0.0399(13) 0.0353(12) 0.0004(12) 0.0078(9) -0.0035(12) C2 0.0309(11) 0.0423(15) 0.0298(11) 0.0007(10) 0.0082(9) -0.0025(11) C3 0.0344(12) 0.0467(16) 0.0318(11) -0.0004(11) 0.0073(10) -0.0018(12) C4 0.0393(13) 0.059(2) 0.0466(14) -0.0102(12) 0.0099(12) 0.0019(13) C5 0.0331(11) 0.0413(14) 0.0294(10) -0.0005(11) 0.0066(9) -0.0056(11) C6 0.0499(15) 0.058(2) 0.0607(16) -0.0052(13) 0.0302(13) -0.0006(15) C7 0.0612(17) 0.077(2) 0.0520(16) 0.0039(16) 0.0259(14) 0.0197(16) C8 0.0279(10) 0.0354(13) 0.0341(11) -0.0003(10) 0.0052(8) 0.0013(11) C9 0.0346(11) 0.0368(14) 0.0460(13) 0.0028(12) 0.0103(10) 0.0009(12) C10 0.0345(11) 0.0525(16) 0.0487(13) 0.0018(13) 0.0062(10) 0.0188(15) C11 0.0402(12) 0.0626(19) 0.0346(12) -0.0066(14) 0.0071(10) 0.0035(14) C12 0.0490(14) 0.0475(16) 0.0358(13) 0.0020(12) 0.0117(11) -0.0068(12) C13 0.0384(12) 0.0347(13) 0.0352(12) 0.0033(10) 0.0050(10) 0.0007(10) _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_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 C5 . 1.746(2) ? S1 C6 . 1.804(3) ? S2 C5 . 1.747(3) ? S2 C7 . 1.817(3) ? O1 C1 . 1.221(3) ? O2 C3 . 1.233(3) ? C1 C2 . 1.487(3) ? C1 C8 . 1.496(3) ? C2 C5 . 1.369(3) ? C2 C3 . 1.472(3) ? C3 C4 . 1.495(4) ? C4 H4A . 0.9600 ? C4 H4B . 0.9600 ? C4 H4C . 0.9600 ? C6 C7 . 1.497(4) ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 C13 . 1.385(3) ? C8 C9 . 1.394(3) ? C9 C10 . 1.378(3) ? C9 H9A . 0.9300 ? C10 C11 . 1.387(4) ? C10 H10A . 0.9300 ? C11 C12 . 1.377(4) ? C11 H11A . 0.9300 ? C12 C13 . 1.389(3) ? C12 H12A . 0.9300 ? C13 H13A . 0.9300 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 S1 C6 . . 95.83(12) ? C5 S2 C7 . . 96.03(13) ? O1 C1 C2 . . 121.3(2) ? O1 C1 C8 . . 119.2(2) ? C2 C1 C8 . . 119.2(2) ? C5 C2 C3 . . 120.3(2) ? C5 C2 C1 . . 118.4(2) ? C3 C2 C1 . . 121.3(2) ? O2 C3 C2 . . 120.6(2) ? O2 C3 C4 . . 119.5(2) ? C2 C3 C4 . . 119.6(2) ? C3 C4 H4A . . 109.5 ? C3 C4 H4B . . 109.5 ? H4A C4 H4B . . 109.5 ? C3 C4 H4C . . 109.5 ? H4A C4 H4C . . 109.5 ? H4B C4 H4C . . 109.5 ? C2 C5 S1 . . 122.47(19) ? C2 C5 S2 . . 123.26(17) ? S1 C5 S2 . . 114.27(14) ? C7 C6 S1 . . 107.8(2) ? C7 C6 H6A . . 110.1 ? S1 C6 H6A . . 110.1 ? C7 C6 H6B . . 110.1 ? S1 C6 H6B . . 110.1 ? H6A C6 H6B . . 108.5 ? C6 C7 S2 . . 108.04(19) ? C6 C7 H7A . . 110.1 ? S2 C7 H7A . . 110.1 ? C6 C7 H7B . . 110.1 ? S2 C7 H7B . . 110.1 ? H7A C7 H7B . . 108.4 ? C13 C8 C9 . . 119.0(2) ? C13 C8 C1 . . 121.5(2) ? C9 C8 C1 . . 119.3(2) ? C10 C9 C8 . . 120.5(2) ? C10 C9 H9A . . 119.7 ? C8 C9 H9A . . 119.7 ? C9 C10 C11 . . 120.1(3) ? C9 C10 H10A . . 120.0 ? C11 C10 H10A . . 120.0 ? C12 C11 C10 . . 120.0(2) ? C12 C11 H11A . . 120.0 ? C10 C11 H11A . . 120.0 ? C11 C12 C13 . . 120.0(3) ? C11 C12 H12A . . 120.0 ? C13 C12 H12A . . 120.0 ? C8 C13 C12 . . 120.5(2) ? C8 C13 H13A . . 119.8 ? C12 C13 H13A . . 119.8 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C1 C2 C5 . . . . -36.8(4) ? C8 C1 C2 C5 . . . . 137.1(2) ? O1 C1 C2 C3 . . . . 142.2(3) ? C8 C1 C2 C3 . . . . -43.9(3) ? C5 C2 C3 O2 . . . . -21.0(4) ? C1 C2 C3 O2 . . . . 160.0(2) ? C5 C2 C3 C4 . . . . 153.3(2) ? C1 C2 C3 C4 . . . . -25.7(3) ? C3 C2 C5 S1 . . . . -172.03(19) ? C1 C2 C5 S1 . . . . 7.0(3) ? C3 C2 C5 S2 . . . . 8.2(3) ? C1 C2 C5 S2 . . . . -172.79(18) ? C6 S1 C5 C2 . . . . -165.4(2) ? C6 S1 C5 S2 . . . . 14.38(17) ? C7 S2 C5 C2 . . . . -172.7(2) ? C7 S2 C5 S1 . . . . 7.48(18) ? C5 S1 C6 C7 . . . . -36.6(2) ? S1 C6 C7 S2 . . . . 45.7(3) ? C5 S2 C7 C6 . . . . -32.4(3) ? O1 C1 C8 C13 . . . . 149.8(3) ? C2 C1 C8 C13 . . . . -24.2(3) ? O1 C1 C8 C9 . . . . -24.3(4) ? C2 C1 C8 C9 . . . . 161.7(2) ? C13 C8 C9 C10 . . . . 0.6(3) ? C1 C8 C9 C10 . . . . 174.8(2) ? C8 C9 C10 C11 . . . . -1.4(4) ? C9 C10 C11 C12 . . . . 1.7(4) ? C10 C11 C12 C13 . . . . -1.1(4) ? C9 C8 C13 C12 . . . . 0.0(3) ? C1 C8 C13 C12 . . . . -174.0(2) ? C11 C12 C13 C8 . . . . 0.2(4) ?