#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226941.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_2226941
loop_
_publ_author_name
'Rad, Nazar'
'Teslenko, Yuri'
'Obushak, Mykola'
'Pavlyuk, Volodymyr'
'Marciniak, Bernard'
_publ_section_title
;
 2-[(2Z,3E)-2-Hydroxyimino-5-phenyl-2,3-dihydro-3-thienylidene]-2-phenylacetonitrile
;
_journal_coeditor_code           IM2200
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1924
_journal_paper_doi               10.1107/S1600536810024955
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H12 N2 O S'
_chemical_formula_moiety         'C18 H12 N2 O S'
_chemical_formula_sum            'C18 H12 N2 O S'
_chemical_formula_weight         304.37
_chemical_name_systematic
;
2-[(2Z,3E)-2-Hydroxyimino-5-phenyl-2,3-dihydro-3-
thienylidene]-2-phenylacetonitrile
;
_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                 90.471(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9826(5)
_cell_length_b                   21.3400(7)
_cell_length_c                   8.7253(5)
_cell_measurement_reflns_used    2240
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.52
_cell_volume                     1486.29(14)
_computing_cell_refinement       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur3 CCD'
_diffrn_measurement_method       ω
_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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9461
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2008)'
_exptl_crystal_colour            'translucent red'
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0359
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0639P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2240
_reflns_number_total             3024
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2200.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226941
_cod_database_fobs_code          2226941
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_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 0.06721(5) 0.580998(19) 0.13057(5) 0.04795(16) Uani d . 1 . .
O O1 0.36433(15) 0.55770(6) -0.00007(15) 0.0580(3) Uani d . 1 . .
H H1A 0.4546 0.5529 -0.0427 0.097(8) Uiso calc R 1 . .
N N1 0.32525(16) 0.50389(6) 0.08232(15) 0.0450(3) Uani d . 1 . .
N N2 0.4444(2) 0.36514(9) 0.2067(2) 0.0826(6) Uani d . 1 . .
C C1 -0.2697(2) 0.64260(8) 0.1895(2) 0.0559(5) Uani d . 1 . .
H H1 -0.1866 0.6575 0.1250 0.0632(16) Uiso calc R 1 . .
C C2 -0.4127(3) 0.67764(10) 0.2115(2) 0.0680(5) Uani d . 1 . .
H H2 -0.4250 0.7159 0.1614 0.0632(16) Uiso calc R 1 . .
C C3 -0.5363(2) 0.65684(9) 0.3058(2) 0.0623(5) Uani d . 1 . .
H H3 -0.6328 0.6805 0.3198 0.0632(16) Uiso calc R 1 . .
C C4 -0.5168(2) 0.60064(9) 0.3797(2) 0.0628(5) Uani d . 1 . .
H H4 -0.6001 0.5864 0.4448 0.0632(16) Uiso calc R 1 . .
C C5 -0.3749(2) 0.56499(9) 0.3585(2) 0.0544(5) Uani d . 1 . .
H H5 -0.3638 0.5268 0.4090 0.0632(16) Uiso calc R 1 . .
C C6 -0.24840(18) 0.58563(7) 0.26236(17) 0.0408(4) Uani d . 1 . .
C C7 -0.09669(18) 0.54839(7) 0.23836(16) 0.0390(4) Uani d . 1 . .
C C8 -0.06423(19) 0.48957(7) 0.28617(18) 0.0415(4) Uani d . 1 . .
H H8 -0.1393 0.4670 0.3456 0.0632(16) Uiso calc R 1 . .
C C9 0.18360(19) 0.51144(7) 0.14809(17) 0.0388(3) Uani d . 1 . .
C C10 0.09381(18) 0.46385(7) 0.23958(16) 0.0375(3) Uani d . 1 . .
C C11 0.14890(19) 0.40472(7) 0.27078(16) 0.0391(4) Uani d . 1 . .
C C12 0.3148(2) 0.38504(8) 0.2323(2) 0.0523(4) Uani d . 1 . .
C C13 0.04594(19) 0.35461(7) 0.34177(17) 0.0378(3) Uani d . 1 . .
C C14 -0.1207(2) 0.34566(7) 0.29922(18) 0.0427(4) Uani d . 1 . .
H H14 -0.1707 0.3724 0.2282 0.0632(16) Uiso calc R 1 . .
C C15 -0.2121(2) 0.29741(7) 0.36173(19) 0.0491(4) Uani d . 1 . .
H H15 -0.3234 0.2919 0.3324 0.0632(16) Uiso calc R 1 . .
C C16 -0.1409(2) 0.25741(8) 0.4668(2) 0.0550(5) Uani d . 1 . .
H H16 -0.2034 0.2248 0.5082 0.0632(16) Uiso calc R 1 . .
C C17 0.0237(2) 0.26584(8) 0.5107(2) 0.0545(4) Uani d . 1 . .
H H17 0.0718 0.2393 0.5833 0.0632(16) Uiso calc R 1 . .
C C18 0.1177(2) 0.31341(8) 0.44739(18) 0.0468(4) Uani d . 1 . .
H H18 0.2297 0.3180 0.4754 0.0632(16) 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'
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'
N N 0.0061 0.0033 '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 S1 C7 . . 90.83(7) ?
N1 O1 H1A . . 109.5 ?
C9 N1 O1 . . 109.24(12) ?
C2 C1 C6 . . 120.82(17) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C3 C2 C1 . . 120.71(18) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 119.24(17) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C3 C4 C5 . . 120.74(18) ?
C3 C4 H4 . . 119.6 ?
C5 C4 H4 . . 119.6 ?
C4 C5 C6 . . 120.52(17) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
C1 C6 C5 . . 117.97(15) ?
C1 C6 C7 . . 120.69(14) ?
C5 C6 C7 . . 121.34(14) ?
C8 C7 C6 . . 128.19(14) ?
C8 C7 S1 . . 113.06(11) ?
C6 C7 S1 . . 118.74(11) ?
C7 C8 C10 . . 115.79(13) ?
C7 C8 H8 . . 122.1 ?
C10 C8 H8 . . 122.1 ?
N1 C9 C10 . . 125.99(14) ?
N1 C9 S1 . . 122.34(12) ?
C10 C9 S1 . . 111.62(11) ?
C11 C10 C8 . . 125.41(13) ?
C11 C10 C9 . . 125.87(13) ?
C8 C10 C9 . . 108.69(13) ?
C10 C11 C12 . . 121.48(14) ?
C10 C11 C13 . . 124.78(13) ?
C12 C11 C13 . . 113.72(13) ?
N2 C12 C11 . . 174.86(18) ?
C14 C13 C18 . . 118.49(14) ?
C14 C13 C11 . . 121.21(13) ?
C18 C13 C11 . . 120.23(14) ?
C15 C14 C13 . . 120.35(15) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C16 C15 C14 . . 120.80(16) ?
C16 C15 H15 . . 119.6 ?
C14 C15 H15 . . 119.6 ?
C15 C16 C17 . . 119.55(16) ?
C15 C16 H16 . . 120.2 ?
C17 C16 H16 . . 120.2 ?
C16 C17 C18 . . 120.36(16) ?
C16 C17 H17 . . 119.8 ?
C18 C17 H17 . . 119.8 ?
C17 C18 C13 . . 120.44(16) ?
C17 C18 H18 . . 119.8 ?
C13 C18 H18 . . 119.8 ?
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 C9 . 1.7571(15) ?
S1 C7 . 1.7609(15) ?
O1 N1 . 1.3916(17) ?
O1 H1A . 0.8200 ?
N1 C9 . 1.282(2) ?
N2 C12 . 1.142(2) ?
C1 C2 . 1.379(2) ?
C1 C6 . 1.382(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.365(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.370(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.390(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.465(2) ?
C7 C8 . 1.347(2) ?
C8 C10 . 1.438(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.480(2) ?
C10 C11 . 1.363(2) ?
C11 C12 . 1.432(2) ?
C11 C13 . 1.487(2) ?
C13 C14 . 1.391(2) ?
C13 C18 . 1.394(2) ?
C14 C15 . 1.377(2) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.373(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.378(2) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.380(2) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
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
O1 H1A N1 3_665 0.82 2.16 2.900(2) 150
O1 H1A N2 3_665 0.82 2.40 2.888(2) 119
C1 H1 S1 . 0.93 2.60 3.041(2) 109
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
C6 C1 C2 C3 . . . . 0.1(3) ?
C1 C2 C3 C4 . . . . 0.3(3) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C3 C4 C5 C6 . . . . 0.4(3) ?
C2 C1 C6 C5 . . . . -0.3(3) ?
C2 C1 C6 C7 . . . . 179.74(18) ?
C4 C5 C6 C1 . . . . 0.0(3) ?
C4 C5 C6 C7 . . . . -179.99(16) ?
C1 C6 C7 C8 . . . . -172.02(16) ?
C5 C6 C7 C8 . . . . 8.0(3) ?
C1 C6 C7 S1 . . . . 6.3(2) ?
C5 C6 C7 S1 . . . . -173.67(13) ?
C9 S1 C7 C8 . . . . 0.99(13) ?
C9 S1 C7 C6 . . . . -177.60(12) ?
C6 C7 C8 C10 . . . . 177.39(14) ?
S1 C7 C8 C10 . . . . -1.04(18) ?
O1 N1 C9 C10 . . . . 176.52(13) ?
O1 N1 C9 S1 . . . . -0.34(19) ?
C7 S1 C9 N1 . . . . 176.57(14) ?
C7 S1 C9 C10 . . . . -0.69(12) ?
C7 C8 C10 C11 . . . . -177.64(15) ?
C7 C8 C10 C9 . . . . 0.49(19) ?
N1 C9 C10 C11 . . . . 1.3(3) ?
S1 C9 C10 C11 . . . . 178.39(13) ?
N1 C9 C10 C8 . . . . -176.87(15) ?
S1 C9 C10 C8 . . . . 0.27(16) ?
C8 C10 C11 C12 . . . . -174.00(15) ?
C9 C10 C11 C12 . . . . 8.2(2) ?
C8 C10 C11 C13 . . . . 7.8(2) ?
C9 C10 C11 C13 . . . . -169.97(14) ?
C10 C11 C12 N2 . . . . 177(2) ?
C13 C11 C12 N2 . . . . -5(2) ?
C10 C11 C13 C14 . . . . 41.3(2) ?
C12 C11 C13 C14 . . . . -137.00(15) ?
C10 C11 C13 C18 . . . . -142.00(16) ?
C12 C11 C13 C18 . . . . 39.7(2) ?
C18 C13 C14 C15 . . . . 0.6(2) ?
C11 C13 C14 C15 . . . . 177.37(14) ?
C13 C14 C15 C16 . . . . 0.0(2) ?
C14 C15 C16 C17 . . . . 0.3(2) ?
C15 C16 C17 C18 . . . . -1.2(3) ?
C16 C17 C18 C13 . . . . 1.9(2) ?
C14 C13 C18 C17 . . . . -1.5(2) ?
C11 C13 C18 C17 . . . . -178.36(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656156
2 PubChem 56840505
