#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/46/2214625.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_2214625
loop_
_publ_author_name
'Dridi, K.'
'El Efrit, M. L.'
_publ_section_title
;
 2-Anilino-5-benzoyl-4-phenyl-1,3-thiazole
;
_journal_coeditor_code           DN2220
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3632
_journal_page_last               o3632
_journal_paper_doi               10.1107/S1600536807035635
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C22 H16 N2 O S'
_chemical_formula_moiety         'C22 H16 N2 O S'
_chemical_formula_sum            'C22 H16 N2 O S'
_chemical_formula_weight         356.43
_chemical_name_systematic
;
2-Anilino-5-benzoyl-4-phenyl-1,3-thiazole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.33(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.163(4)
_cell_length_b                   9.433(4)
_cell_length_c                   14.533(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     1780.6(10)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius MACH3'
_diffrn_measurement_method       'non-profiled 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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6093
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        4
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0501P)²+0.2524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1164
_reflns_number_gt                2704
_reflns_number_total             4298
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2220.cif
_cod_data_source_block           I
_cod_original_cell_volume        1780.7(10)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2214625
_cod_database_fobs_code          2214625
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
H H23 0.4049(15) 0.014(2) 0.5334(15) 0.051(6) Uiso d . 1
S S1 0.45331(4) 0.35859(5) 0.61163(4) 0.04442(15) Uani d . 1
N N1 0.55404(11) 0.16658(16) 0.53728(11) 0.0406(4) Uani d . 1
N N2 0.38926(12) 0.09407(19) 0.55532(13) 0.0474(4) Uani d . 1
C C1 0.46481(13) 0.19246(19) 0.56396(13) 0.0393(4) Uani d . 1
C C2 0.61980(13) 0.2793(2) 0.55837(13) 0.0393(4) Uani d . 1
C C3 0.58128(13) 0.3926(2) 0.60089(14) 0.0419(5) Uani d . 1
C C4 0.62158(16) 0.5284(2) 0.63774(14) 0.0485(5) Uani d . 1
C C5 0.73535(16) 0.5524(2) 0.66124(14) 0.0473(5) Uani d . 1
C C6 0.77439(18) 0.6847(2) 0.64381(15) 0.0582(6) Uani d . 1
H H6 0.7307 0.7557 0.6163 0.070 Uiso calc R 1
C C7 0.8793(2) 0.7100(3) 0.66781(18) 0.0721(8) Uani d . 1
H H7 0.9059 0.7980 0.6553 0.087 Uiso calc R 1
C C8 0.9439(2) 0.6068(3) 0.70969(19) 0.0771(8) Uani d . 1
H H8 1.0141 0.6246 0.7247 0.093 Uiso calc R 1
C C9 0.90544(18) 0.4770(3) 0.72957(17) 0.0698(7) Uani d . 1
H H9 0.9491 0.4080 0.7597 0.084 Uiso calc R 1
C C10 0.80140(17) 0.4493(3) 0.70459(15) 0.0557(6) Uani d . 1
H H10 0.7756 0.3608 0.7170 0.067 Uiso calc R 1
C C11 0.30362(13) 0.0973(2) 0.60371(14) 0.0431(5) Uani d . 1
C C12 0.28562(15) -0.0198(2) 0.65595(15) 0.0549(6) Uani d . 1
H H12 0.3287 -0.0984 0.6588 0.066 Uiso calc R 1
C C13 0.20274(18) -0.0194(3) 0.70408(17) 0.0692(7) Uani d . 1
H H13 0.1900 -0.0985 0.7387 0.083 Uiso calc R 1
C C14 0.13943(16) 0.0965(3) 0.70108(17) 0.0674(7) Uani d . 1
H H14 0.0850 0.0968 0.7347 0.081 Uiso calc R 1
C C15 0.15660(15) 0.2113(3) 0.64847(17) 0.0606(6) Uani d . 1
H H15 0.1134 0.2897 0.6461 0.073 Uiso calc R 1
C C16 0.23814(14) 0.2122(2) 0.59834(15) 0.0502(5) Uani d . 1
H H16 0.2484 0.2898 0.5615 0.060 Uiso calc R 1
C C17 0.72450(13) 0.2650(2) 0.53328(13) 0.0408(4) Uani d . 1
C C18 0.76104(16) 0.3639(2) 0.47657(16) 0.0547(5) Uani d . 1
H H18 0.7196 0.4392 0.4523 0.066 Uiso calc R 1
C C19 0.85990(18) 0.3503(3) 0.45611(18) 0.0711(7) Uani d . 1
H H19 0.8847 0.4172 0.4183 0.085 Uiso calc R 1
C C20 0.92083(17) 0.2400(3) 0.49075(19) 0.0731(7) Uani d . 1
H H20 0.9870 0.2318 0.4767 0.088 Uiso calc R 1
C C21 0.88460(16) 0.1402(3) 0.54673(18) 0.0671(7) Uani d . 1
H H21 0.9266 0.0652 0.5706 0.080 Uiso calc R 1
C C22 0.78631(15) 0.1514(2) 0.56741(15) 0.0520(5) Uani d . 1
H H22 0.7615 0.0830 0.6042 0.062 Uiso calc R 1
O O1 0.56177(12) 0.62208(16) 0.65279(13) 0.0742(5) Uani d . 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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-3 -4 -1
-3 4 -1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 S1 C3 88.98(9)
C1 N1 C2 110.51(15)
C1 N2 C11 124.74(17)
C1 N2 H23 114.9(13)
C11 N2 H23 117.4(14)
N1 C1 N2 121.53(17)
N1 C1 S1 115.19(14)
N2 C1 S1 123.27(14)
C3 C2 N1 115.96(15)
C3 C2 C17 127.27(17)
N1 C2 C17 116.77(16)
C2 C3 C4 135.42(17)
C2 C3 S1 109.24(14)
C4 C3 S1 115.35(14)
O1 C4 C3 119.58(19)
O1 C4 C5 119.83(19)
C3 C4 C5 120.54(18)
C10 C5 C6 119.4(2)
C10 C5 C4 121.85(19)
C6 C5 C4 118.7(2)
C5 C6 C7 119.4(2)
C5 C6 H6 120.3
C7 C6 H6 120.3
C8 C7 C6 120.7(2)
C8 C7 H7 119.7
C6 C7 H7 119.7
C7 C8 C9 120.2(2)
C7 C8 H8 119.9
C9 C8 H8 119.9
C8 C9 C10 119.7(3)
C8 C9 H9 120.1
C10 C9 H9 120.1
C9 C10 C5 120.5(2)
C9 C10 H10 119.7
C5 C10 H10 119.7
C16 C11 C12 119.87(18)
C16 C11 N2 121.77(19)
C12 C11 N2 118.35(18)
C11 C12 C13 119.5(2)
C11 C12 H12 120.2
C13 C12 H12 120.2
C14 C13 C12 120.6(2)
C14 C13 H13 119.7
C12 C13 H13 119.7
C15 C14 C13 119.7(2)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C16 120.6(2)
C14 C15 H15 119.7
C16 C15 H15 119.7
C11 C16 C15 119.6(2)
C11 C16 H16 120.2
C15 C16 H16 120.2
C18 C17 C22 119.60(18)
C18 C17 C2 120.71(18)
C22 C17 C2 119.69(17)
C17 C18 C19 119.6(2)
C17 C18 H18 120.2
C19 C18 H18 120.2
C20 C19 C18 120.6(2)
C20 C19 H19 119.7
C18 C19 H19 119.7
C19 C20 C21 120.1(2)
C19 C20 H20 120.0
C21 C20 H20 120.0
C20 C21 C22 120.2(2)
C20 C21 H21 119.9
C22 C21 H21 119.9
C21 C22 C17 119.9(2)
C21 C22 H22 120.1
C17 C22 H22 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.730(2)
S1 C3 1.7465(18)
N1 C1 1.318(2)
N1 C2 1.374(2)
N2 C1 1.351(2)
N2 C11 1.423(2)
N2 H23 0.86(2)
C2 C3 1.372(3)
C2 C17 1.488(2)
C3 C4 1.456(3)
C4 O1 1.226(2)
C4 C5 1.498(3)
C5 C10 1.386(3)
C5 C6 1.388(3)
C6 C7 1.389(3)
C6 H6 0.9300
C7 C8 1.369(4)
C7 H7 0.9300
C8 C9 1.374(4)
C8 H8 0.9300
C9 C10 1.383(3)
C9 H9 0.9300
C10 H10 0.9300
C11 C16 1.380(3)
C11 C12 1.382(3)
C12 C13 1.388(3)
C12 H12 0.9300
C13 C14 1.371(3)
C13 H13 0.9300
C14 C15 1.366(3)
C14 H14 0.9300
C15 C16 1.392(3)
C15 H15 0.9300
C16 H16 0.9300
C17 C18 1.382(3)
C17 C22 1.387(3)
C18 C19 1.387(3)
C18 H18 0.9300
C19 C20 1.360(3)
C19 H19 0.9300
C20 C21 1.379(3)
C20 H20 0.9300
C21 C22 1.379(3)
C21 H21 0.9300
C22 H22 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
_geom_hbond_publ_flag
N2 H23 N1 3_656 0.858(19) 2.10(2) 2.956(3) 172(2) 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
C2 N1 C1 N2 -176.33(18)
C2 N1 C1 S1 2.8(2)
C11 N2 C1 N1 162.18(19)
C11 N2 C1 S1 -16.8(3)
C3 S1 C1 N1 -3.38(16)
C3 S1 C1 N2 175.70(18)
C1 N1 C2 C3 -0.3(2)
C1 N1 C2 C17 179.33(16)
N1 C2 C3 C4 177.6(2)
C17 C2 C3 C4 -2.1(4)
N1 C2 C3 S1 -2.1(2)
C17 C2 C3 S1 178.25(16)
C1 S1 C3 C2 2.93(15)
C1 S1 C3 C4 -176.84(16)
C2 C3 C4 O1 163.3(2)
S1 C3 C4 O1 -17.0(3)
C2 C3 C4 C5 -19.4(4)
S1 C3 C4 C5 160.29(15)
O1 C4 C5 C10 136.6(2)
C3 C4 C5 C10 -40.7(3)
O1 C4 C5 C6 -39.6(3)
C3 C4 C5 C6 143.1(2)
C10 C5 C6 C7 1.7(3)
C4 C5 C6 C7 178.04(19)
C5 C6 C7 C8 -1.0(4)
C6 C7 C8 C9 -0.8(4)
C7 C8 C9 C10 1.9(4)
C8 C9 C10 C5 -1.2(3)
C6 C5 C10 C9 -0.6(3)
C4 C5 C10 C9 -176.8(2)
C1 N2 C11 C16 55.9(3)
C1 N2 C11 C12 -125.2(2)
C16 C11 C12 C13 -1.3(3)
N2 C11 C12 C13 179.8(2)
C11 C12 C13 C14 -0.7(4)
C12 C13 C14 C15 1.5(4)
C13 C14 C15 C16 -0.4(4)
C12 C11 C16 C15 2.4(3)
N2 C11 C16 C15 -178.74(19)
C14 C15 C16 C11 -1.6(3)
C3 C2 C17 C18 -56.6(3)
N1 C2 C17 C18 123.8(2)
C3 C2 C17 C22 123.2(2)
N1 C2 C17 C22 -56.4(3)
C22 C17 C18 C19 -1.4(3)
C2 C17 C18 C19 178.4(2)
C17 C18 C19 C20 0.5(4)
C18 C19 C20 C21 0.1(4)
C19 C20 C21 C22 0.3(4)
C20 C21 C22 C17 -1.3(4)
C18 C17 C22 C21 1.8(3)
C2 C17 C22 C21 -178.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1042166
2 PubChem 1241166
