#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202531.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2202531 loop_ _publ_author_name 'Sundar, T.V.' 'Parthasarathi, V.' 'Garc\'ia-Granda, S.' 'Jain, Abhinandan' 'Pardasani, R.T.' _publ_section_title 2-(3-Ethyl-2,3,4,5-tetrahydro-4-oxo-2-thioxo-4-thiazolidin-5-ylidene)-1,2-dihydroacenaphthylen-1-one _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1967 _journal_page_last o1969 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C17 H11 N O2 S2' _chemical_formula_moiety 'C17 H11 N O2 S2' _chemical_formula_sum 'C17 H11 N O2 S2' _chemical_formula_weight 325.39 _chemical_melting_point 483 _chemical_name_systematic ; 2-(3-Ethyl-2,3,4,5-tetrahydro-4-oxo-2-thioxo-4-thiazolidin-5-ylidene)- 1,2-dihydroacenaphthylen-1-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 92.911(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.382(5) _cell_length_b 26.375(5) _cell_length_c 7.511(5) _cell_measurement_reflns_used 2248 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 68.0 _cell_measurement_theta_min 2.0 _cell_volume 1460.5(14) _computing_cell_refinement 'DENZO and SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 1997--2000)' _computing_data_reduction 'DENZO and SCALEPACK' _computing_molecular_graphics 'WINGX (Farrugia, 1999)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'DIRDIF99 (Beurskens et al., 1999)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.860 _diffrn_measured_fraction_theta_max 0.860 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0591 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 4416 _diffrn_reflns_theta_full 69.19 _diffrn_reflns_theta_max 69.19 _diffrn_reflns_theta_min 3.35 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 3.357 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 672 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.246 _refine_diff_density_min -0.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2338 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.0941 _refine_ls_R_factor_gt 0.0517 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.1394P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1231 _refine_ls_wR_factor_ref 0.1512 _reflns_number_gt 1427 _reflns_number_total 2338 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6302.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '483 K' was changed to '483' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '483 K' was changed to '483' - the value should be numeric and without a unit designator. '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2202531 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' loop_ _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 _atom_site_type_symbol S1 0.24945(12) 0.36221(4) 0.16933(13) 0.0567(3) Uani d . 1 . . S S2 0.31324(16) 0.47252(4) 0.19844(17) 0.0803(4) Uani d . 1 . . S C9 0.5131(4) 0.22481(12) 0.2912(5) 0.0482(9) Uani d . 1 . . C O2 0.7115(3) 0.32990(10) 0.3940(4) 0.0705(8) Uani d . 1 . . O O1 0.0956(3) 0.27197(10) 0.0949(4) 0.0719(8) Uani d . 1 . . O C1 0.2213(5) 0.24661(13) 0.1580(5) 0.0501(9) Uani d . 1 . . C N1 0.5417(4) 0.39931(11) 0.3175(4) 0.0578(8) Uani d . 1 . . N C11 0.4093(4) 0.18059(13) 0.2474(5) 0.0475(9) Uani d . 1 . . C C14 0.5741(5) 0.34747(14) 0.3285(5) 0.0526(9) Uani d . 1 . . C C13 0.4153(4) 0.31942(12) 0.2469(5) 0.0485(9) Uani d . 1 . . C C2 0.2360(4) 0.19139(13) 0.1697(4) 0.0496(9) Uani d . 1 . . C C3 0.1202(5) 0.15282(14) 0.1220(5) 0.0593(10) Uani d . 1 . . C H3 0.0058 0.1594 0.0695 0.071 Uiso calc R 1 . . H C12 0.3961(4) 0.26867(13) 0.2382(5) 0.0484(9) Uani d . 1 . . C C8 0.6845(5) 0.21850(14) 0.3658(5) 0.0560(10) Uani d . 1 . . C H8 0.7577 0.2464 0.3938 0.067 Uiso calc R 1 . . H C10 0.4711(5) 0.13139(13) 0.2767(5) 0.0534(9) Uani d . 1 . . C C15 0.3819(5) 0.41470(13) 0.2348(5) 0.0562(10) Uani d . 1 . . C C6 0.6470(5) 0.12590(14) 0.3556(5) 0.0600(10) Uani d . 1 . . C H6 0.6947 0.0938 0.3781 0.072 Uiso calc R 1 . . H C4 0.1794(5) 0.10254(15) 0.1546(5) 0.0664(11) Uani d . 1 . . C H4 0.1008 0.0759 0.1256 0.080 Uiso calc R 1 . . H C5 0.3477(5) 0.09190(14) 0.2272(5) 0.0617(11) Uani d . 1 . . C H5 0.3825 0.0583 0.2447 0.074 Uiso calc R 1 . . H C7 0.7480(5) 0.16844(14) 0.3996(5) 0.0608(11) Uani d . 1 . . C H7 0.8631 0.1642 0.4538 0.073 Uiso calc R 1 . . H C16 0.6765(5) 0.43519(15) 0.3980(6) 0.0682(11) Uani d . 1 . . C H16A 0.7362 0.4199 0.5027 0.082 Uiso calc R 1 . . H H16B 0.6152 0.4656 0.4353 0.082 Uiso calc R 1 . . H C17 0.8163(6) 0.44903(17) 0.2669(6) 0.0860(14) Uani d . 1 . . C H17A 0.8818 0.4192 0.2353 0.129 Uiso calc R 1 . . H H17B 0.8991 0.4734 0.3201 0.129 Uiso calc R 1 . . H H17C 0.7569 0.4633 0.1618 0.129 Uiso calc R 1 . . H 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 0.0507(5) 0.0554(6) 0.0633(7) 0.0027(4) -0.0032(5) 0.0048(4) S2 0.0796(7) 0.0547(7) 0.1057(11) 0.0064(5) -0.0043(7) 0.0071(6) C9 0.0444(18) 0.056(2) 0.044(2) -0.0009(16) -0.0018(17) -0.0010(17) O2 0.0597(16) 0.0598(17) 0.089(2) 0.0015(13) -0.0251(16) 0.0002(15) O1 0.0545(15) 0.0635(17) 0.095(2) 0.0026(13) -0.0194(15) 0.0051(15) C1 0.050(2) 0.055(2) 0.045(3) -0.0004(17) -0.0041(18) 0.0018(17) N1 0.0527(17) 0.0535(19) 0.066(2) -0.0021(14) -0.0044(17) -0.0022(15) C11 0.0469(18) 0.052(2) 0.043(2) -0.0026(16) 0.0006(18) -0.0044(17) C14 0.052(2) 0.056(2) 0.049(3) -0.0013(17) -0.0059(19) -0.0011(17) C13 0.0474(18) 0.050(2) 0.048(2) -0.0020(15) -0.0002(18) -0.0005(17) C2 0.0466(19) 0.056(2) 0.045(3) -0.0012(16) -0.0021(18) 0.0026(16) C3 0.051(2) 0.063(3) 0.062(3) -0.0055(18) -0.0086(19) -0.0040(19) C12 0.0441(18) 0.054(2) 0.046(2) 0.0028(16) -0.0010(17) 0.0043(17) C8 0.050(2) 0.057(2) 0.060(3) 0.0004(17) -0.0039(19) -0.0019(18) C10 0.060(2) 0.053(2) 0.047(3) 0.0012(17) 0.000(2) -0.0039(17) C15 0.054(2) 0.056(2) 0.059(3) 0.0013(17) 0.002(2) 0.0005(18) C6 0.059(2) 0.056(2) 0.064(3) 0.0070(18) -0.006(2) -0.0015(19) C4 0.066(2) 0.061(3) 0.071(3) -0.013(2) -0.003(2) -0.010(2) C5 0.068(2) 0.050(2) 0.067(3) -0.0017(18) 0.003(2) -0.0047(19) C7 0.052(2) 0.061(3) 0.068(3) 0.0071(18) -0.008(2) -0.001(2) C16 0.067(2) 0.060(2) 0.076(3) -0.005(2) -0.012(2) -0.006(2) C17 0.073(3) 0.081(3) 0.105(4) -0.008(2) 0.010(3) -0.001(3) 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 C13 . 1.743(4) ? S1 C15 . 1.751(4) ? S2 C15 . 1.626(4) ? C9 C8 . 1.367(5) ? C9 C11 . 1.425(4) ? C9 C12 . 1.486(4) ? O2 C14 . 1.198(4) ? O1 C1 . 1.220(4) ? C1 C2 . 1.463(5) ? C1 C12 . 1.513(5) ? N1 C15 . 1.367(5) ? N1 C14 . 1.390(4) ? N1 C16 . 1.480(5) ? C11 C10 . 1.389(5) ? C11 C2 . 1.408(5) ? C14 C13 . 1.491(5) ? C13 C12 . 1.347(4) ? C2 C3 . 1.365(5) ? C3 C4 . 1.414(5) ? C3 H3 . 0.93 ? C8 C7 . 1.420(5) ? C8 H8 . 0.93 ? C10 C6 . 1.407(5) ? C10 C5 . 1.421(5) ? C6 C7 . 1.378(5) ? C6 H6 . 0.93 ? C4 C5 . 1.360(6) ? C4 H4 . 0.93 ? C5 H5 . 0.93 ? C7 H7 . 0.93 ? C16 C17 . 1.507(5) ? C16 H16A . 0.97 ? C16 H16B . 0.97 ? C17 H17A . 0.96 ? C17 H17B . 0.96 ? C17 H17C . 0.96 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C13 S1 C15 92.61(18) ? C8 C9 C11 118.1(3) ? C8 C9 C12 135.9(3) ? C11 C9 C12 106.1(3) ? O1 C1 C2 128.5(3) ? O1 C1 C12 124.1(3) ? C2 C1 C12 107.5(3) ? C15 N1 C14 117.4(3) yes C15 N1 C16 122.9(3) yes C14 N1 C16 119.7(3) yes C10 C11 C2 122.6(3) ? C10 C11 C9 124.0(3) ? C2 C11 C9 113.4(3) ? O2 C14 N1 123.0(3) ? O2 C14 C13 127.5(3) ? N1 C14 C13 109.5(3) ? C12 C13 C14 126.2(3) ? C12 C13 S1 123.8(3) ? C14 C13 S1 109.9(2) ? C3 C2 C11 120.1(3) ? C3 C2 C1 133.1(3) ? C11 C2 C1 106.8(3) ? C2 C3 C4 118.0(4) ? C2 C3 H3 121.0 ? C4 C3 H3 121.0 ? C13 C12 C9 134.6(3) ? C13 C12 C1 119.1(3) ? C9 C12 C1 106.3(3) ? C9 C8 C7 118.5(3) ? C9 C8 H8 120.8 ? C7 C8 H8 120.8 ? C11 C10 C6 116.8(3) ? C11 C10 C5 116.3(4) ? C6 C10 C5 126.9(3) ? N1 C15 S2 127.5(3) ? N1 C15 S1 110.5(3) ? S2 C15 S1 122.0(2) ? C7 C6 C10 119.6(3) ? C7 C6 H6 120.2 ? C10 C6 H6 120.2 ? C5 C4 C3 122.1(4) ? C5 C4 H4 119.0 ? C3 C4 H4 119.0 ? C4 C5 C10 120.9(3) ? C4 C5 H5 119.5 ? C10 C5 H5 119.5 ? C6 C7 C8 123.0(4) ? C6 C7 H7 118.5 ? C8 C7 H7 118.5 ? N1 C16 C17 110.9(3) ? N1 C16 H16A 109.5 ? C17 C16 H16A 109.5 ? N1 C16 H16B 109.5 ? C17 C16 H16B 109.5 ? H16A C16 H16B 108.0 ? C16 C17 H17A 109.5 ? C16 C17 H17B 109.5 ? H17A C17 H17B 109.5 ? C16 C17 H17C 109.5 ? H17A C17 H17C 109.5 ? H17B C17 H17C 109.5 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C3 H3 O2 4_465 0.93 2.50 3.423(5) 172 yes C7 H7 O1 4_666 0.93 2.59 3.290(5) 132 yes C8 H8 O2 . 0.93 2.23 2.952(4) 134 yes 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 C8 C9 C11 C10 0.3(6) C12 C9 C11 C10 -179.9(3) C8 C9 C11 C2 -179.3(3) C12 C9 C11 C2 0.4(4) C15 N1 C14 O2 178.0(4) C16 N1 C14 O2 -3.4(5) C15 N1 C14 C13 -1.6(4) C16 N1 C14 C13 177.0(3) O2 C14 C13 C12 2.5(6) N1 C14 C13 C12 -177.9(3) O2 C14 C13 S1 -179.7(3) N1 C14 C13 S1 -0.2(4) C15 S1 C13 C12 179.1(3) C15 S1 C13 C14 1.3(3) C10 C11 C2 C3 0.9(5) C9 C11 C2 C3 -179.4(3) C10 C11 C2 C1 -179.1(3) C9 C11 C2 C1 0.6(4) O1 C1 C2 C3 -2.1(7) C12 C1 C2 C3 178.7(4) O1 C1 C2 C11 177.9(4) C12 C1 C2 C11 -1.3(4) C11 C2 C3 C4 0.6(5) C1 C2 C3 C4 -179.4(3) C14 C13 C12 C9 -3.2(7) S1 C13 C12 C9 179.3(3) C14 C13 C12 C1 177.1(3) S1 C13 C12 C1 -0.3(5) C8 C9 C12 C13 -1.2(8) C11 C9 C12 C13 179.1(4) C8 C9 C12 C1 178.5(4) C11 C9 C12 C1 -1.2(4) O1 C1 C12 C13 2.1(5) C2 C1 C12 C13 -178.6(3) O1 C1 C12 C9 -177.7(3) C2 C1 C12 C9 1.6(4) C11 C9 C8 C7 -1.5(5) C12 C9 C8 C7 178.8(4) C2 C11 C10 C6 -179.9(3) C9 C11 C10 C6 0.5(5) C2 C11 C10 C5 -1.4(5) C9 C11 C10 C5 179.0(3) C14 N1 C15 S2 -177.9(3) C16 N1 C15 S2 3.6(5) C14 N1 C15 S1 2.6(4) C16 N1 C15 S1 -175.9(3) C13 S1 C15 N1 -2.1(3) C13 S1 C15 S2 178.3(2) C11 C10 C6 C7 0.0(5) C5 C10 C6 C7 -178.4(4) C2 C3 C4 C5 -1.6(6) C3 C4 C5 C10 1.2(6) C11 C10 C5 C4 0.3(6) C6 C10 C5 C4 178.7(4) C10 C6 C7 C8 -1.2(6) C9 C8 C7 C6 2.0(6) C15 N1 C16 C17 -93.0(4) C14 N1 C16 C17 88.5(4) _cod_database_fobs_code 2202531 _journal_paper_doi 10.1107/S160053680302600X