#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/16/2231643.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_2231643
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Khan, Salman A.'
'Tahir, M. Nawaz'
_publ_section_title
;
 2-[(2-Chlorobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile
;
_journal_coeditor_code           NK2106
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2355
_journal_paper_doi               10.1107/S1600536811032302
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H13 Cl N2 S'
_chemical_formula_moiety         'C16 H13 Cl N2 S'
_chemical_formula_sum            'C16 H13 Cl N2 S'
_chemical_formula_weight         300.79
_chemical_name_systematic
;
2-[(2-Chlorobenzylidene)amino]-4,5,6,7-tetrahydro-1-benzothiophene-
3-carbonitrile
;
_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                85.975(2)
_cell_angle_beta                 80.806(2)
_cell_angle_gamma                73.003(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3383(4)
_cell_length_b                   8.6885(4)
_cell_length_c                   10.5746(5)
_cell_measurement_reflns_used    2308
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      3.00
_cell_volume                     723.00(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.20
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEXII 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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10003
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.337
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0369
_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)+(0.0542P)²+0.2530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2308
_reflns_number_total             2600
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nk2106.cif
_cod_data_source_block           I
_cod_database_code               2231643
_cod_database_fobs_code          2231643
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
Cl Cl1 0.51410(9) 0.59840(7) -0.31788(6) 0.0866(2) Uani 1.000 -16
S S1 0.05883(6) 0.76273(6) 0.05536(4) 0.0534(2) Uani 1.000 -16
N N1 0.0435(3) 0.2524(2) 0.3132(2) 0.0764(7) Uani 1.000 -16
N N2 0.24264(18) 0.44103(18) 0.02432(13) 0.0474(5) Uani 1.000 -16
C C1 0.1187(2) 0.5590(2) 0.09452(16) 0.0444(5) Uani 1.000 -16
C C2 0.0275(2) 0.53040(19) 0.20896(15) 0.0409(5) Uani 1.000 -16
C C3 -0.0859(2) 0.67215(19) 0.26797(15) 0.0402(5) Uani 1.000 -16
C C4 -0.1898(2) 0.6775(2) 0.39739(16) 0.0481(6) Uani 1.000 -16
C C5 -0.3072(3) 0.8451(2) 0.42743(19) 0.0596(6) Uani 1.000 -16
C C6 -0.2276(3) 0.9751(2) 0.3795(2) 0.0639(7) Uani 1.000 -16
C C7 -0.1776(3) 0.9748(2) 0.23394(18) 0.0563(6) Uani 1.000 -16
C C8 -0.0812(2) 0.8060(2) 0.19563(16) 0.0450(5) Uani 1.000 -16
C C9 0.0415(2) 0.3740(2) 0.26452(17) 0.0490(6) Uani 1.000 -16
C C10 0.3285(2) 0.4785(2) -0.07655(17) 0.0515(6) Uani 1.000 -16
C C11 0.4641(2) 0.3591(2) -0.15131(16) 0.0467(5) Uani 1.000 -16
C C12 0.5574(2) 0.4006(2) -0.26298(18) 0.0505(6) Uani 1.000 -16
C C13 0.6858(2) 0.2868(3) -0.33329(18) 0.0553(6) Uani 1.000 -16
C C14 0.7236(2) 0.1295(3) -0.29270(19) 0.0581(6) Uani 1.000 -16
C C15 0.6354(3) 0.0838(3) -0.1829(2) 0.0631(7) Uani 1.000 -16
C C16 0.5064(3) 0.1976(2) -0.11318(19) 0.0580(6) Uani 1.000 -16
H H4A -0.11493 0.64359 0.46182 0.0577 Uiso 1.000 -16
H H4B -0.25684 0.60246 0.40122 0.0577 Uiso 1.000 -16
H H5A -0.40913 0.86058 0.38900 0.0715 Uiso 1.000 -16
H H5B -0.34027 0.85337 0.51947 0.0715 Uiso 1.000 -16
H H6A -0.12747 0.96148 0.41971 0.0766 Uiso 1.000 -16
H H6B -0.30654 1.07855 0.40410 0.0766 Uiso 1.000 -16
H H7A -0.27819 1.01182 0.19234 0.0676 Uiso 1.000 -16
H H7B -0.10754 1.04641 0.20812 0.0676 Uiso 1.000 -16
H H10 0.30434 0.58581 -0.10391 0.0618 Uiso 1.000 -16
H H13 0.74600 0.31718 -0.40782 0.0664 Uiso 1.000 -16
H H14 0.80998 0.05264 -0.33990 0.0697 Uiso 1.000 -16
H H15 0.66233 -0.02358 -0.15544 0.0757 Uiso 1.000 -16
H H16 0.44656 0.16560 -0.03915 0.0696 Uiso 1.000 -16
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C1 S1 C8 92.06(8) no
C1 N2 C10 120.23(15) no
S1 C1 N2 126.07(13) no
S1 C1 C2 109.88(12) no
N2 C1 C2 124.04(15) no
C1 C2 C3 114.07(14) no
C1 C2 C9 123.61(15) no
C3 C2 C9 122.32(15) no
C2 C3 C4 125.31(14) no
C2 C3 C8 111.71(15) no
C4 C3 C8 122.86(15) no
C3 C4 C5 112.01(14) no
C4 C5 C6 112.83(19) no
C5 C6 C7 112.49(17) no
C6 C7 C8 108.21(14) no
S1 C8 C3 112.24(13) no
S1 C8 C7 122.74(13) no
C3 C8 C7 124.94(16) no
N1 C9 C2 175.9(2) no
N2 C10 C11 122.19(16) no
C10 C11 C12 122.04(15) no
C10 C11 C16 120.95(16) no
C12 C11 C16 117.01(16) no
Cl1 C12 C11 120.35(13) no
Cl1 C12 C13 117.94(15) no
C11 C12 C13 121.71(17) no
C12 C13 C14 119.53(18) no
C13 C14 C15 120.6(2) no
C14 C15 C16 119.8(2) no
C11 C16 C15 121.36(19) no
C3 C4 H4A 109.00 no
C3 C4 H4B 109.00 no
C5 C4 H4A 109.00 no
C5 C4 H4B 109.00 no
H4A C4 H4B 108.00 no
C4 C5 H5A 109.00 no
C4 C5 H5B 109.00 no
C6 C5 H5A 109.00 no
C6 C5 H5B 109.00 no
H5A C5 H5B 108.00 no
C5 C6 H6A 109.00 no
C5 C6 H6B 109.00 no
C7 C6 H6A 109.00 no
C7 C6 H6B 109.00 no
H6A C6 H6B 108.00 no
C6 C7 H7A 110.00 no
C6 C7 H7B 110.00 no
C8 C7 H7A 110.00 no
C8 C7 H7B 110.00 no
H7A C7 H7B 108.00 no
N2 C10 H10 119.00 no
C11 C10 H10 119.00 no
C12 C13 H13 120.00 no
C14 C13 H13 120.00 no
C13 C14 H14 120.00 no
C15 C14 H14 120.00 no
C14 C15 H15 120.00 no
C16 C15 H15 120.00 no
C11 C16 H16 119.00 no
C15 C16 H16 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C12 1.7277(18) no
S1 C1 1.7322(17) no
S1 C8 1.7243(18) no
N1 C9 1.139(2) no
N2 C1 1.383(2) no
N2 C10 1.265(2) no
C1 C2 1.371(2) no
C2 C3 1.428(2) no
C2 C9 1.422(2) no
C3 C4 1.494(2) no
C3 C8 1.353(2) no
C4 C5 1.521(2) no
C5 C6 1.491(3) no
C6 C7 1.529(3) no
C7 C8 1.500(2) no
C10 C11 1.457(2) no
C11 C12 1.393(3) no
C11 C16 1.390(2) no
C12 C13 1.381(3) no
C13 C14 1.364(3) no
C14 C15 1.371(3) no
C15 C16 1.380(3) no
C4 H4A 0.9700 no
C4 H4B 0.9700 no
C5 H5A 0.9700 no
C5 H5B 0.9700 no
C6 H6A 0.9700 no
C6 H6B 0.9700 no
C7 H7A 0.9700 no
C7 H7B 0.9700 no
C10 H10 0.9300 no
C13 H13 0.9300 no
C14 H14 0.9300 no
C15 H15 0.9300 no
C16 H16 0.9300 no
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
C5 H5A Cg 2_565 0.97 2.87 3.744(3) 151 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
_geom_torsion_publ_flag
C8 S1 C1 N2 -176.35(16) no
C8 S1 C1 C2 2.04(14) no
C1 S1 C8 C7 175.39(17) no
C1 S1 C8 C3 -1.37(15) no
C10 N2 C1 C2 -175.64(17) no
C1 N2 C10 C11 177.94(16) no
C10 N2 C1 S1 2.5(3) no
S1 C1 C2 C3 -2.3(2) no
S1 C1 C2 C9 176.99(14) no
N2 C1 C2 C3 176.19(16) no
N2 C1 C2 C9 -4.6(3) no
C9 C2 C3 C8 -177.98(16) no
C9 C2 C3 C4 5.9(3) no
C1 C2 C3 C4 -174.81(16) no
C1 C2 C3 C8 1.3(2) no
C2 C3 C4 C5 -175.60(17) no
C8 C3 C4 C5 8.7(2) no
C2 C3 C8 S1 0.3(2) no
C2 C3 C8 C7 -176.34(18) no
C4 C3 C8 S1 176.53(13) no
C4 C3 C8 C7 -0.2(3) no
C3 C4 C5 C6 -38.3(2) no
C4 C5 C6 C7 60.9(2) no
C5 C6 C7 C8 -48.8(3) no
C6 C7 C8 S1 -156.62(16) no
C6 C7 C8 C3 19.7(3) no
N2 C10 C11 C12 179.42(17) no
N2 C10 C11 C16 -0.9(3) no
C10 C11 C12 Cl1 -0.3(2) no
C10 C11 C12 C13 179.96(17) no
C16 C11 C12 Cl1 -179.97(15) no
C16 C11 C12 C13 0.3(3) no
C10 C11 C16 C15 -179.6(2) no
C12 C11 C16 C15 0.1(3) no
Cl1 C12 C13 C14 179.92(15) no
C11 C12 C13 C14 -0.3(3) no
C12 C13 C14 C15 -0.1(3) no
C13 C14 C15 C16 0.5(3) no
C14 C15 C16 C11 -0.5(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7859978
2 PubChem 9585831
