#------------------------------------------------------------------------------
#$Date: 2025-08-19 14:52:15 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/72/2217228.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_2217228
loop_
_publ_author_name
'Dufresne, Stéphane'
'Bourque, Alex N.'
'Skene, W. G.'
_publ_section_title
;
 (E)-5-(2-Thienylmethyleneamino)quinolin-8-ol
;
_journal_coeditor_code           NG2406
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o316
_journal_page_last               o316
_journal_paper_doi               10.1107/S1600536807066652
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C14 H10 N2 O S'
_chemical_formula_moiety         'C14 H10 N2 O S'
_chemical_formula_sum            'C14 H10 N2 O S'
_chemical_formula_weight         254.30
_chemical_name_systematic
;
(E)-5-(2-Thienylmethyleneamino)quinolin-8-ol
;
_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                 92.926(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6798(4)
_cell_length_b                   9.8592(4)
_cell_length_c                   15.7512(7)
_cell_measurement_reflns_used    7426
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.91
_cell_measurement_theta_min      5.29
_cell_volume                     1191.07(9)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (Marris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31904
_diffrn_reflns_theta_full        73.16
_diffrn_reflns_theta_max         73.16
_diffrn_reflns_theta_min         5.29
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  1080
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    2.312
_exptl_absorpt_correction_T_max  0.8932
_exptl_absorpt_correction_T_min  0.8549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.619
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0537
_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)+(0.0968P)²+0.157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1388
_reflns_number_gt                2152
_reflns_number_total             2377
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2406.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217228
_cod_database_fobs_code          2217228
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
S S1 0.43366(6) 0.82399(4) 0.21499(3) 0.0464(2) Uani d . 1
O O1 0.10263(18) 0.13156(13) -0.09352(7) 0.0446(3) Uani d . 1
H H1 0.0556 0.0746 -0.0623 0.067 Uiso calc R 1
N N1 0.0099(2) 0.14942(15) 0.07194(9) 0.0394(3) Uani d . 1
N N2 0.29207(18) 0.59227(14) 0.09825(9) 0.0406(3) Uani d . 1
C C1 -0.0336(3) 0.16030(18) 0.15190(11) 0.0449(4) Uani d . 1
H H1A -0.0985 0.0886 0.1752 0.054 Uiso calc R 1
C C2 0.0107(3) 0.2718(2) 0.20431(11) 0.0460(4) Uani d . 1
H H2 -0.0225 0.2741 0.2616 0.055 Uiso calc R 1
C C3 0.1018(2) 0.37649(19) 0.17187(11) 0.0419(4) Uani d . 1
H H3 0.1327 0.4524 0.2066 0.050 Uiso calc R 1
C C4 0.1505(2) 0.37229(17) 0.08639(10) 0.0361(4) Uani d . 1
C C5 0.2413(2) 0.47908(17) 0.04695(11) 0.0373(4) Uani d . 1
C C6 0.2810(2) 0.46462(17) -0.03706(11) 0.0393(4) Uani d . 1
H H6 0.3422 0.5352 -0.0637 0.047 Uiso calc R 1
C C7 0.2332(2) 0.34810(17) -0.08420(11) 0.0397(4) Uani d . 1
H H7 0.2618 0.3414 -0.1420 0.048 Uiso calc R 1
C C8 0.1456(2) 0.24404(17) -0.04735(10) 0.0367(4) Uani d . 1
C C9 0.1013(2) 0.25436(16) 0.03912(9) 0.0354(4) Uani d . 1
C C10 0.3002(2) 0.70894(18) 0.06355(12) 0.0424(4) Uani d . 1
H H10 0.2655 0.7176 0.0050 0.051 Uiso calc R 1
C C11 0.3600(2) 0.82854(16) 0.10947(12) 0.0420(4) Uani d . 1
C C12 0.3671(3) 0.95730(19) 0.07858(13) 0.0529(5) Uani d . 1
H H12 0.3312 0.9809 0.0219 0.063 Uiso calc R 1
C C13 0.4333(3) 1.0526(2) 0.13929(14) 0.0554(5) Uani d . 1
H H13 0.4470 1.1465 0.1277 0.066 Uiso calc R 1
C C14 0.4751(3) 0.99469(18) 0.21584(12) 0.0474(4) Uani d . 1
H H14 0.5216 1.0430 0.2640 0.057 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C14 S1 C11 91.92(9)
C8 O1 H1 109.5
C1 N1 C9 117.25(14)
C10 N2 C5 118.84(15)
N1 C1 C2 123.84(17)
N1 C1 H1A 118.1
C2 C1 H1A 118.1
C3 C2 C1 119.08(16)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 120.04(16)
C2 C3 H3 120.0
C4 C3 H3 120.0
C3 C4 C9 116.48(15)
C3 C4 C5 123.54(15)
C9 C4 C5 119.98(15)
C6 C5 N2 123.97(15)
C6 C5 C4 118.63(15)
N2 C5 C4 117.35(15)
C5 C6 C7 121.74(16)
C5 C6 H6 119.1
C7 C6 H6 119.1
C8 C7 C6 120.53(16)
C8 C7 H7 119.7
C6 C7 H7 119.7
O1 C8 C7 119.70(14)
O1 C8 C9 120.47(14)
C7 C8 C9 119.83(15)
N1 C9 C4 123.30(14)
N1 C9 C8 117.39(14)
C4 C9 C8 119.30(15)
N2 C10 C11 122.82(17)
N2 C10 H10 118.6
C11 C10 H10 118.6
C12 C11 C10 126.81(18)
C12 C11 S1 110.52(14)
C10 C11 S1 122.67(13)
C11 C12 C13 113.39(18)
C11 C12 H12 123.3
C13 C12 H12 123.3
C14 C13 C12 112.38(18)
C14 C13 H13 123.8
C12 C13 H13 123.8
C13 C14 S1 111.78(14)
C13 C14 H14 124.1
S1 C14 H14 124.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C14 1.7127(18)
S1 C11 1.7289(19)
O1 C8 1.358(2)
O1 H1 0.8400
N1 C1 1.324(2)
N1 C9 1.367(2)
N2 C10 1.276(2)
N2 C5 1.421(2)
C1 C2 1.406(3)
C1 H1A 0.9500
C2 C3 1.361(3)
C2 H2 0.9500
C3 C4 1.416(2)
C3 H3 0.9500
C4 C9 1.421(2)
C4 C5 1.423(2)
C5 C6 1.380(2)
C6 C7 1.406(2)
C6 H6 0.9500
C7 C8 1.372(2)
C7 H7 0.9500
C8 C9 1.424(2)
C10 C11 1.446(2)
C10 H10 0.9500
C11 C12 1.362(3)
C12 C13 1.417(3)
C12 H12 0.9500
C13 C14 1.358(3)
C13 H13 0.9500
C14 H14 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
_geom_hbond_publ_flag
O1 H1 N1 3_555 0.840 2.269 2.927(2) 135.5 y
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
C9 N1 C1 C2 -0.8(3)
N1 C1 C2 C3 0.8(3)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C9 -0.8(2)
C2 C3 C4 C5 178.12(16)
C10 N2 C5 C6 33.6(2)
C10 N2 C5 C4 -149.15(16)
C3 C4 C5 C6 -179.47(15)
C9 C4 C5 C6 -0.6(2)
C3 C4 C5 N2 3.2(2)
C9 C4 C5 N2 -177.93(14)
N2 C5 C6 C7 177.58(15)
C4 C5 C6 C7 0.4(2)
C5 C6 C7 C8 -0.4(3)
C6 C7 C8 O1 -179.12(15)
C6 C7 C8 C9 0.5(3)
C1 N1 C9 C4 0.0(2)
C1 N1 C9 C8 -178.93(16)
C3 C4 C9 N1 0.8(2)
C5 C4 C9 N1 -178.15(15)
C3 C4 C9 C8 179.70(15)
C5 C4 C9 C8 0.7(2)
O1 C8 C9 N1 -2.1(2)
C7 C8 C9 N1 178.23(15)
O1 C8 C9 C4 178.95(14)
C7 C8 C9 C4 -0.7(2)
C5 N2 C10 C11 -176.40(16)
N2 C10 C11 C12 -177.5(2)
N2 C10 C11 S1 2.4(3)
C14 S1 C11 C12 -0.57(17)
C14 S1 C11 C10 179.52(17)
C10 C11 C12 C13 -179.54(19)
S1 C11 C12 C13 0.6(2)
C11 C12 C13 C14 -0.2(3)
C12 C13 C14 S1 -0.2(2)
C11 S1 C14 C13 0.45(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655418
2 PubChem 139074094
