#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/31/2233114.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_2233114
loop_
_publ_author_name
'Jiang, Jun-Rong'
'Xu, Feng'
'Ke, Zhong-Lu'
'Li, Li'
_publ_section_title
;
 (5S)-5-Methyl-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
;
_journal_coeditor_code           CV5203
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o34
_journal_paper_doi               10.1107/S1600536811051312
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H9 N O S2'
_chemical_formula_moiety         'C10 H9 N O S2'
_chemical_formula_sum            'C10 H9 N O S2'
_chemical_formula_weight         223.30
_chemical_name_systematic
;
(5S)-5-Methyl-3-phenyl-2-sulfanylidene-1,3-thiazolidin-4-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8527(4)
_cell_length_b                   8.6643(5)
_cell_length_c                   17.5572(15)
_cell_measurement_reflns_used    3919
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.12
_cell_measurement_theta_min      2.32
_cell_volume                     1042.44(12)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2008)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2008)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku AFC10/Saturn724+'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9028
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.475
_exptl_absorpt_correction_T_max  0.9186
_exptl_absorpt_correction_T_min  0.8723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.170
_refine_ls_abs_structure_details 'Flack (1983), 1155 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0281
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0326P)²+0.0860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0636
_reflns_number_gt                2561
_reflns_number_total             2777
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5203.cif
_cod_data_source_block           I
_cod_database_code               2233114
_cod_database_fobs_code          2233114
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_symmetry_multiplicity
S S1 0.11471(5) 0.55991(4) 0.42516(2) 0.02375(9) Uani d . 1 1
S S2 0.13997(6) 0.70725(4) 0.57733(2) 0.02665(10) Uani d U 1 1
O O1 0.53389(18) 0.27885(14) 0.46834(6) 0.0334(3) Uani d . 1 1
N N3 0.36082(17) 0.47158(13) 0.52694(6) 0.0177(2) Uani d . 1 1
C C2 0.2145(2) 0.57762(16) 0.51556(8) 0.0186(3) Uani d U 1 1
C C4 0.4056(2) 0.37374(17) 0.46629(8) 0.0212(3) Uani d . 1 1
C C5 0.2751(2) 0.40173(16) 0.39840(8) 0.0204(3) Uani d . 1 1
H H5 0.1937 0.3075 0.3899 0.025 Uiso calc R 1 1
C C6 0.3913(2) 0.4338(2) 0.32607(8) 0.0285(3) Uani d . 1 1
H H6A 0.4889 0.3525 0.3188 0.034 Uiso calc R 1 1
H H6B 0.4569 0.5339 0.3306 0.034 Uiso calc R 1 1
H H6C 0.3027 0.4357 0.2823 0.034 Uiso calc R 1 1
C C7 0.4603(2) 0.45370(16) 0.59871(7) 0.0184(3) Uani d . 1 1
C C8 0.3715(2) 0.36714(18) 0.65529(8) 0.0246(3) Uani d . 1 1
H H8 0.2451 0.3249 0.6476 0.030 Uiso calc R 1 1
C C9 0.4698(3) 0.34305(19) 0.72335(9) 0.0285(4) Uani d . 1 1
H H9 0.4112 0.2829 0.7624 0.034 Uiso calc R 1 1
C C10 0.6522(2) 0.40624(18) 0.73445(8) 0.0280(3) Uani d . 1 1
H H10 0.7178 0.3909 0.7815 0.034 Uiso calc R 1 1
C C11 0.7409(2) 0.4923(2) 0.67723(9) 0.0274(3) Uani d . 1 1
H H11 0.8671 0.5348 0.6852 0.033 Uiso calc R 1 1
C C12 0.6448(2) 0.51620(16) 0.60833(8) 0.0226(3) Uani d . 1 1
H H12 0.7045 0.5742 0.5687 0.027 Uiso calc R 1 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 0.02356(17) 0.02662(18) 0.02108(17) 0.00623(15) -0.00460(16) -0.00175(15)
S2 0.02865(19) 0.02565(18) 0.02565(19) 0.00662(16) 0.00106(18) -0.00678(16)
O1 0.0377(7) 0.0365(7) 0.0259(6) 0.0192(6) -0.0044(5) -0.0058(5)
N3 0.0179(5) 0.0197(5) 0.0155(5) 0.0002(5) -0.0008(5) -0.0004(4)
C2 0.0180(6) 0.0183(6) 0.0194(6) -0.0016(5) 0.0012(5) 0.0008(5)
C4 0.0225(8) 0.0226(7) 0.0186(7) 0.0013(6) 0.0004(6) -0.0003(6)
C5 0.0230(7) 0.0198(7) 0.0186(6) 0.0002(6) -0.0007(6) -0.0027(6)
C6 0.0301(8) 0.0347(8) 0.0208(7) 0.0031(8) 0.0021(6) 0.0006(7)
C7 0.0216(6) 0.0182(7) 0.0154(6) 0.0014(5) -0.0005(5) -0.0012(5)
C8 0.0227(7) 0.0286(7) 0.0227(7) -0.0028(7) 0.0021(6) -0.0003(6)
C9 0.0374(9) 0.0291(8) 0.0189(7) -0.0009(7) 0.0043(7) 0.0031(6)
C10 0.0355(9) 0.0292(8) 0.0193(7) 0.0057(7) -0.0065(7) -0.0017(6)
C11 0.0254(7) 0.0281(8) 0.0286(8) -0.0028(6) -0.0078(6) -0.0007(6)
C12 0.0243(7) 0.0205(6) 0.0231(7) -0.0025(6) -0.0008(6) 0.0023(6)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 S1 C5 93.72(7)
C2 N3 C4 117.10(11)
C2 N3 C7 122.96(11)
C4 N3 C7 119.87(12)
N3 C2 S2 126.00(10)
N3 C2 S1 111.18(10)
S2 C2 S1 122.82(9)
O1 C4 N3 123.54(13)
O1 C4 C5 124.46(13)
N3 C4 C5 112.01(12)
C4 C5 C6 112.18(12)
C4 C5 S1 105.97(10)
C6 C5 S1 113.16(10)
C4 C5 H5 108.5
C6 C5 H5 108.5
S1 C5 H5 108.5
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C12 C7 C8 121.67(13)
C12 C7 N3 119.76(12)
C8 C7 N3 118.49(13)
C7 C8 C9 119.05(15)
C7 C8 H8 120.5
C9 C8 H8 120.5
C10 C9 C8 120.14(15)
C10 C9 H9 119.9
C8 C9 H9 119.9
C9 C10 C11 120.47(14)
C9 C10 H10 119.8
C11 C10 H10 119.8
C10 C11 C12 120.01(15)
C10 C11 H11 120.0
C12 C11 H11 120.0
C7 C12 C11 118.64(14)
C7 C12 H12 120.7
C11 C12 H12 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.7350(14)
S1 C5 1.8184(15)
S2 C2 1.6427(14)
O1 C4 1.2043(17)
N3 C2 1.3746(17)
N3 C4 1.3951(18)
N3 C7 1.4412(17)
C4 C5 1.510(2)
C5 C6 1.5245(19)
C5 H5 1.0000
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 C12 1.3856(19)
C7 C8 1.386(2)
C8 C9 1.387(2)
C8 H8 0.9500
C9 C10 1.379(2)
C9 H9 0.9500
C10 C11 1.391(2)
C10 H10 0.9500
C11 C12 1.393(2)
C11 H11 0.9500
C12 H12 0.9500
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
C5 H5 Cg 4_456 1.00 2.47 3.4321(16) 162
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
C4 N3 C2 S2 -178.34(11)
C7 N3 C2 S2 4.66(19)
C4 N3 C2 S1 1.17(15)
C7 N3 C2 S1 -175.83(10)
C5 S1 C2 N3 -0.14(11)
C5 S1 C2 S2 179.39(9)
C2 N3 C4 O1 177.98(14)
C7 N3 C4 O1 -4.9(2)
C2 N3 C4 C5 -1.81(17)
C7 N3 C4 C5 175.29(12)
O1 C4 C5 C6 -54.3(2)
N3 C4 C5 C6 125.48(13)
O1 C4 C5 S1 -178.26(13)
N3 C4 C5 S1 1.53(14)
C2 S1 C5 C4 -0.78(10)
C2 S1 C5 C6 -124.12(11)
C2 N3 C7 C12 -102.04(16)
C4 N3 C7 C12 81.04(17)
C2 N3 C7 C8 81.10(18)
C4 N3 C7 C8 -95.83(16)
C12 C7 C8 C9 0.2(2)
N3 C7 C8 C9 177.02(13)
C7 C8 C9 C10 0.8(2)
C8 C9 C10 C11 -1.1(2)
C9 C10 C11 C12 0.5(2)
C8 C7 C12 C11 -0.8(2)
N3 C7 C12 C11 -177.60(13)
C10 C11 C12 C7 0.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1150794
