#------------------------------------------------------------------------------
#$Date: 2022-05-16 12:05:50 +0300 (Mon, 16 May 2022) $
#$Revision: 275447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105269.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105269
loop_
_publ_author_name
'Lin, Qiao'
'Lin, Zirui'
'Chen, Xiuwen'
'Li, Bin'
_publ_section_title
;
 Crystal structure of 3-(2-methylbenzyl)thiazolidin-2-one, C11H13ONS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              727
_journal_page_last               728
_journal_paper_doi               10.1515/ncrs-2019-0922
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C11 H13 N O S'
_chemical_formula_sum            'C11 H13 N O S'
_chemical_formula_weight         207.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 98.354(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0795(6)
_cell_length_b                   7.2294(5)
_cell_length_c                   17.5898(14)
_cell_measurement_reflns_used    3166
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      29.2130
_cell_measurement_theta_min      3.0280
_cell_volume                     1016.52(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -56.00  39.00   1.00    1.00    --   11.74 -57.00-120.00   95
  2  ω    -15.00  75.00   1.00    1.00    --   11.74  77.00 150.00   90
  3  ω    -11.00  78.00   1.00    1.00    --   11.74  57.00  30.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0835177000
_diffrn_orient_matrix_UB_12      0.0082482000
_diffrn_orient_matrix_UB_13      -0.0188340000
_diffrn_orient_matrix_UB_21      0.0299737000
_diffrn_orient_matrix_UB_22      0.0165868000
_diffrn_orient_matrix_UB_23      -0.0353095000
_diffrn_orient_matrix_UB_31      -0.0019133000
_diffrn_orient_matrix_UB_32      -0.0963688000
_diffrn_orient_matrix_UB_33      -0.0076596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6153
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.341
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0362P)²+0.3138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1590
_reflns_number_total             1789
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0922_suppl.cif
_cod_data_source_block           xz161
_cod_database_code               8105269
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.392
_oxdiff_exptl_absorpt_empirical_full_min 0.762
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7100(2) -0.0415(2) 0.30904(10) 0.0220(4) Uani 1 1 d . . . . .
C2 C 0.5656(2) -0.1431(2) 0.28410(10) 0.0279(4) Uani 1 1 d . . . . .
H2 H 0.565878 -0.227039 0.244064 0.034 Uiso 1 1 calc R . . . .
C3 C 0.4219(2) -0.1219(2) 0.31747(11) 0.0296(4) Uani 1 1 d . . . . .
H3 H 0.326884 -0.190752 0.299690 0.036 Uiso 1 1 calc R . . . .
C4 C 0.4197(2) 0.0013(2) 0.37710(10) 0.0253(4) Uani 1 1 d . . . . .
H4 H 0.323765 0.015410 0.400062 0.030 Uiso 1 1 calc R . . . .
C5 C 0.5621(2) 0.1043(2) 0.40255(10) 0.0220(4) Uani 1 1 d . . . . .
H5 H 0.560620 0.187474 0.442795 0.026 Uiso 1 1 calc R . . . .
C6 C 0.7072(2) 0.0857(2) 0.36904(10) 0.0194(4) Uani 1 1 d . . . . .
C7 C 0.8635(2) 0.1971(2) 0.39843(10) 0.0224(4) Uani 1 1 d . . . . .
H7A H 0.943639 0.116698 0.428703 0.027 Uiso 1 1 calc R . . . .
H7B H 0.913687 0.240417 0.354847 0.027 Uiso 1 1 calc R . . . .
C8 C 0.7434(2) 0.5160(2) 0.40816(10) 0.0223(4) Uani 1 1 d . . . . .
H8A H 0.633339 0.480579 0.382710 0.027 Uiso 1 1 calc R . . . .
H8B H 0.806007 0.567238 0.370055 0.027 Uiso 1 1 calc R . . . .
C9 C 0.7279(2) 0.6586(2) 0.47061(10) 0.0237(4) Uani 1 1 d . . . . .
H9A H 0.622207 0.723931 0.459761 0.028 Uiso 1 1 calc R . . . .
H9B H 0.818128 0.748026 0.473574 0.028 Uiso 1 1 calc R . . . .
C10 C 0.83208(19) 0.3356(2) 0.52149(10) 0.0206(4) Uani 1 1 d . . . . .
C11 C 0.8663(2) -0.0710(3) 0.27289(11) 0.0297(4) Uani 1 1 d . . . . .
H11A H 0.893804 0.041113 0.248266 0.045 Uiso 1 1 calc GR . . . .
H11B H 0.847516 -0.168287 0.235497 0.045 Uiso 1 1 calc GR . . . .
H11C H 0.957094 -0.104536 0.311924 0.045 Uiso 1 1 calc GR . . . .
N1 N 0.83044(16) 0.35536(18) 0.44510(8) 0.0192(3) Uani 1 1 d . . . . .
O1 O 0.88735(14) 0.20338(16) 0.56024(7) 0.0275(3) Uani 1 1 d . . . . .
S1 S 0.73907(5) 0.53136(6) 0.55996(2) 0.02501(16) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C10 S1 C9 92.55(8) . .
C10 N1 C7 120.16(14) . .
C10 N1 C8 117.49(13) . .
C7 N1 C8 119.35(14) . .
O1 C10 S1 123.39(13) . .
O1 C10 N1 126.08(16) . .
N1 C10 S1 110.52(12) . .
C6 C1 C11 121.06(16) . .
C2 C1 C6 118.52(15) . .
C2 C1 C11 120.41(16) . .
C1 C6 C7 119.91(14) . .
C5 C6 C1 119.27(15) . .
C5 C6 C7 120.80(15) . .
C8 C9 S1 106.41(11) . .
C6 C5 C4 121.35(16) . .
N1 C7 C6 113.35(13) . .
C3 C4 C5 119.34(16) . .
N1 C8 C9 107.57(14) . .
C3 C2 C1 121.59(16) . .
C4 C3 C2 119.92(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C10 1.7813(17) .
S1 C9 1.8120(17) .
O1 C10 1.220(2) .
N1 C10 1.349(2) .
N1 C7 1.455(2) .
N1 C8 1.460(2) .
C1 C6 1.402(2) .
C1 C2 1.395(2) .
C1 C11 1.509(2) .
C6 C5 1.393(2) .
C6 C7 1.523(2) .
C9 C8 1.525(2) .
C5 C4 1.389(2) .
C4 C3 1.378(3) .
C2 C3 1.384(3) .
