#------------------------------------------------------------------------------
#$Date: 2025-08-19 16:18:28 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301805 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/86/2228609.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_2228609
loop_
_publ_author_name
'Zhao, Hua-Rong'
'Wang, Hai-Yan'
'Meng, Xiang-Wu'
_publ_section_title
;
 N-(3-Octyl-4-oxo-1,3-thiazolidin-2-ylidene)benzamide
;
_journal_coeditor_code           XU5080
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3285
_journal_paper_doi               10.1107/S1600536810047884
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H24 N2 O2 S'
_chemical_formula_moiety         'C18 H24 N2 O2 S'
_chemical_formula_sum            'C18 H24 N2 O2 S'
_chemical_formula_weight         332.45
_chemical_name_systematic
;
N-(3-Octyl-4-oxo-1,3-thiazolidin-2-ylidene)benzamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.008(5)
_cell_angle_beta                 92.870(4)
_cell_angle_gamma                99.477(4)
_cell_formula_units_Z            2
_cell_length_a                   5.3342(3)
_cell_length_b                   8.6196(5)
_cell_length_c                   20.0775(12)
_cell_measurement_reflns_used    2856
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9615
_cell_measurement_theta_min      4.4521
_cell_volume                     901.41(9)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Oxford Diffraction Nova A'
_diffrn_measurement_method       'ω 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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8685
_diffrn_reflns_theta_full        25.12
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_min         2.05
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0509
_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/[σ²(Fo²)+(0.0633P)²+0.4272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1446
_reflns_number_gt                2371
_reflns_number_total             3205
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5080.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-p 1'
_cod_database_code               2228609
_cod_database_fobs_code          2228609
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
N N2 0.2339(4) 0.3596(2) 0.30556(10) 0.0496(5) Uani d . 1 . .
N N1 -0.1304(4) 0.2176(2) 0.34097(10) 0.0492(5) Uani d . 1 . .
C C9 0.4393(5) 0.4805(3) 0.32305(14) 0.0533(6) Uani d . 1 . .
C C8 0.0680(5) 0.3283(3) 0.35492(12) 0.0464(6) Uani d . 1 . .
C C10 0.4427(5) 0.5499(3) 0.39502(14) 0.0585(7) Uani d . 1 . .
H H10A 0.4422 0.6630 0.3982 0.070 Uiso calc R 1 . .
H H10B 0.5952 0.5337 0.4197 0.070 Uiso calc R 1 . .
O O1 -0.2580(4) 0.2654(2) 0.44909(9) 0.0680(6) Uani d . 1 . .
O O2 0.5957(4) 0.5200(2) 0.28388(11) 0.0733(6) Uani d . 1 . .
S S1 0.16338(13) 0.45285(8) 0.42998(3) 0.0534(2) Uani d . 1 . .
C C7 -0.2882(5) 0.1901(3) 0.39283(13) 0.0508(6) Uani d . 1 . .
C C1 -0.5089(5) 0.0581(3) 0.37455(13) 0.0495(6) Uani d . 1 . .
C C11 0.1963(5) 0.2715(3) 0.23775(13) 0.0569(7) Uani d . 1 . .
H H11A 0.1125 0.1638 0.2402 0.068 Uiso calc R 1 . .
H H11B 0.3613 0.2663 0.2202 0.068 Uiso calc R 1 . .
C C2 -0.5494(5) -0.0279(3) 0.31152(14) 0.0598(7) Uani d . 1 . .
H H2 -0.4341 -0.0064 0.2792 0.072 Uiso calc R 1 . .
C C6 -0.6820(5) 0.0229(3) 0.42264(15) 0.0606(7) Uani d . 1 . .
H H6 -0.6555 0.0795 0.4656 0.073 Uiso calc R 1 . .
C C5 -0.8909(6) -0.0944(4) 0.40707(18) 0.0712(8) Uani d . 1 . .
H H5 -1.0049 -0.1172 0.4395 0.085 Uiso calc R 1 . .
C C4 -0.9324(6) -0.1783(4) 0.34373(19) 0.0735(9) Uani d . 1 . .
H H4 -1.0759 -0.2565 0.3331 0.088 Uiso calc R 1 . .
C C13 -0.0006(7) 0.2535(5) 0.12043(15) 0.0816(10) Uani d . 1 . .
H H13A 0.1634 0.2576 0.1013 0.098 Uiso calc R 1 . .
H H13B -0.0658 0.1432 0.1241 0.098 Uiso calc R 1 . .
C C12 0.0397(6) 0.3448(4) 0.18997(14) 0.0730(9) Uani d . 1 . .
H H12A 0.1241 0.4523 0.1872 0.088 Uiso calc R 1 . .
H H12B -0.1249 0.3508 0.2077 0.088 Uiso calc R 1 . .
C C3 -0.7605(6) -0.1462(4) 0.29574(17) 0.0721(9) Uani d . 1 . .
H H3 -0.7867 -0.2041 0.2530 0.086 Uiso calc R 1 . .
C C15 -0.2276(8) 0.2222(6) 0.00389(18) 0.1053(13) Uani d . 1 . .
H H15A -0.2838 0.1109 0.0076 0.126 Uiso calc R 1 . .
H H15B -0.0679 0.2307 -0.0176 0.126 Uiso calc R 1 . .
C C14 -0.1781(8) 0.3108(5) 0.07302(17) 0.0976(12) Uani d . 1 . .
H H14A -0.3401 0.3090 0.0930 0.117 Uiso calc R 1 . .
H H14B -0.1106 0.4207 0.0691 0.117 Uiso calc R 1 . .
C C17 -0.4809(10) 0.1911(7) -0.1089(2) 0.1358(19) Uani d . 1 . .
H H17A -0.5318 0.0792 -0.1055 0.163 Uiso calc R 1 . .
H H17B -0.3262 0.2022 -0.1326 0.163 Uiso calc R 1 . .
C C16 -0.4209(9) 0.2749(6) -0.04136(19) 0.1114(14) Uani d . 1 . .
H H16A -0.5784 0.2690 -0.0189 0.134 Uiso calc R 1 . .
H H16B -0.3621 0.3859 -0.0452 0.134 Uiso calc R 1 . .
C C18 -0.6818(9) 0.2415(7) -0.1504(2) 0.1289(18) Uani d . 1 . .
H H18A -0.7081 0.1765 -0.1933 0.193 Uiso calc R 1 . .
H H18B -0.6304 0.3505 -0.1567 0.193 Uiso calc R 1 . .
H H18C -0.8375 0.2302 -0.1280 0.193 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N2 C8 . . 116.6(2) ?
C9 N2 C11 . . 120.8(2) ?
C8 N2 C11 . . 122.6(2) ?
C8 N1 C7 . . 116.6(2) ?
O2 C9 N2 . . 122.6(3) ?
O2 C9 C10 . . 126.0(2) ?
N2 C9 C10 . . 111.4(2) ?
N1 C8 N2 . . 119.3(2) ?
N1 C8 S1 . . 128.94(19) ?
N2 C8 S1 . . 111.79(18) ?
C9 C10 S1 . . 108.19(18) ?
C9 C10 H10A . . 110.1 ?
S1 C10 H10A . . 110.1 ?
C9 C10 H10B . . 110.1 ?
S1 C10 H10B . . 110.1 ?
H10A C10 H10B . . 108.4 ?
C8 S1 C10 . . 91.98(12) ?
O1 C7 N1 . . 125.0(2) ?
O1 C7 C1 . . 120.7(2) ?
N1 C7 C1 . . 114.3(2) ?
C2 C1 C6 . . 119.0(2) ?
C2 C1 C7 . . 122.1(2) ?
C6 C1 C7 . . 118.9(2) ?
N2 C11 C12 . . 113.0(2) ?
N2 C11 H11A . . 109.0 ?
C12 C11 H11A . . 109.0 ?
N2 C11 H11B . . 109.0 ?
C12 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C1 C2 C3 . . 120.5(3) ?
C1 C2 H2 . . 119.7 ?
C3 C2 H2 . . 119.7 ?
C5 C6 C1 . . 120.5(3) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
C6 C5 C4 . . 120.2(3) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C4 C3 . . 119.9(3) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C14 C13 C12 . . 115.2(3) ?
C14 C13 H13A . . 108.5 ?
C12 C13 H13A . . 108.5 ?
C14 C13 H13B . . 108.5 ?
C12 C13 H13B . . 108.5 ?
H13A C13 H13B . . 107.5 ?
C11 C12 C13 . . 113.0(3) ?
C11 C12 H12A . . 109.0 ?
C13 C12 H12A . . 109.0 ?
C11 C12 H12B . . 109.0 ?
C13 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
C2 C3 C4 . . 119.8(3) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C14 C15 C16 . . 116.1(4) ?
C14 C15 H15A . . 108.3 ?
C16 C15 H15A . . 108.3 ?
C14 C15 H15B . . 108.3 ?
C16 C15 H15B . . 108.3 ?
H15A C15 H15B . . 107.4 ?
C15 C14 C13 . . 117.1(4) ?
C15 C14 H14A . . 108.0 ?
C13 C14 H14A . . 108.0 ?
C15 C14 H14B . . 108.0 ?
C13 C14 H14B . . 108.0 ?
H14A C14 H14B . . 107.3 ?
C16 C17 C18 . . 116.8(4) ?
C16 C17 H17A . . 108.1 ?
C18 C17 H17A . . 108.1 ?
C16 C17 H17B . . 108.1 ?
C18 C17 H17B . . 108.1 ?
H17A C17 H17B . . 107.3 ?
C17 C16 C15 . . 118.6(4) ?
C17 C16 H16A . . 107.7 ?
C15 C16 H16A . . 107.7 ?
C17 C16 H16B . . 107.7 ?
C15 C16 H16B . . 107.7 ?
H16A C16 H16B . . 107.1 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
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
N2 C9 . 1.380(3) ?
N2 C8 . 1.383(3) ?
N2 C11 . 1.463(3) ?
N1 C8 . 1.297(3) ?
N1 C7 . 1.390(3) ?
C9 O2 . 1.212(3) ?
C9 C10 . 1.493(4) ?
C8 S1 . 1.741(2) ?
C10 S1 . 1.802(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
O1 C7 . 1.221(3) ?
C7 C1 . 1.493(4) ?
C1 C2 . 1.374(4) ?
C1 C6 . 1.395(4) ?
C11 C12 . 1.503(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C2 C3 . 1.384(4) ?
C2 H2 . 0.9300 ?
C6 C5 . 1.371(4) ?
C6 H6 . 0.9300 ?
C5 C4 . 1.373(5) ?
C5 H5 . 0.9300 ?
C4 C3 . 1.384(5) ?
C4 H4 . 0.9300 ?
C13 C14 . 1.492(5) ?
C13 C12 . 1.504(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C3 H3 . 0.9300 ?
C15 C14 . 1.489(5) ?
C15 C16 . 1.502(5) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C17 C16 . 1.451(5) ?
C17 C18 . 1.477(6) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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
C4 H4 O2 1_345 0.93 2.45 3.365(4) 168 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656399
2 PubChem 139080238
