#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/68/1556897.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_1556897
loop_
_publ_author_name
'Alicea-Velázquez, Nilda L.'
'Crundwell, Guy'
_publ_section_title
;
 (E)-1-(5-Methylthiophen-2-yl)-N-(4-nitrophenyl)methanimine
;
_journal_coeditor_code           HB4328
_journal_issue                   12
_journal_name_full               IUCrData
_journal_page_first              x191601
_journal_paper_doi               10.1107/S2414314619016018
_journal_volume                  4
_journal_year                    2019
_chemical_formula_iupac          'C12 H10 N2 O2 S'
_chemical_formula_moiety         'C12 H10 N2 O2 S'
_chemical_formula_sum            'C12 H10 N2 O2 S'
_chemical_formula_weight         246.28
_chemical_melting_point          429
_chemical_name_systematic
;
(E)-1-(5-Methylthiophen-2-yl)-N-(4-nitrophenyl)methanimine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.763(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5979(7)
_cell_length_b                   7.3148(3)
_cell_length_c                   12.5931(6)
_cell_measurement_reflns_used    8567
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      32.6620
_cell_measurement_theta_min      4.4820
_cell_volume                     1155.02(10)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
OLEX2 (Bourhis et al.,  2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1790
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28914
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         33.74
_diffrn_reflns_theta_min         4.28
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.329
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         4318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0446
_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)+(0.0560P)²+0.2252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                3467
_reflns_number_total             4318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4328sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1155.04(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1556897
_cod_database_fobs_code          1556897
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_occupancy
C C1 0.86901(12) 0.5813(3) 0.40834(15) 0.0629(4) Uani d 1
H H1A 0.9087 0.6247 0.4850 0.094 Uiso calc 1
H H1B 0.9003 0.6280 0.3574 0.094 Uiso calc 1
H H1C 0.8706 0.4501 0.4077 0.094 Uiso calc 1
C C2 0.75619(10) 0.64523(16) 0.36931(11) 0.0420(2) Uani d 1
C C3 0.70532(11) 0.71403(19) 0.43482(11) 0.0472(3) Uani d 1
H H3 0.7381 0.7283 0.5142 0.057 Uiso calc 1
C C4 0.59850(11) 0.76142(18) 0.37063(11) 0.0454(3) Uani d 1
H H4 0.5532 0.8095 0.4031 0.054 Uiso calc 1
C C5 0.56820(9) 0.72928(16) 0.25515(10) 0.0383(2) Uani d 1
C C6 0.46547(10) 0.76359(16) 0.16459(11) 0.0399(2) Uani d 1
H H6 0.4091 0.8003 0.1840 0.048 Uiso calc 1
C C7 0.34681(10) 0.76957(16) -0.02564(10) 0.0387(2) Uani d 1
C C8 0.25773(11) 0.68505(19) -0.01918(11) 0.0450(3) Uani d 1
H H8 0.2649 0.6153 0.0452 0.054 Uiso calc 1
C C9 0.15877(11) 0.7036(2) -0.10729(12) 0.0485(3) Uani d 1
H H9 0.0991 0.6471 -0.1031 0.058 Uiso calc 1
C C10 0.15028(11) 0.80772(18) -0.20170(11) 0.0449(3) Uani d 1
C C11 0.23669(12) 0.89611(19) -0.20981(11) 0.0485(3) Uani d 1
H H11 0.2285 0.9684 -0.2734 0.058 Uiso calc 1
C C12 0.33524(11) 0.87551(18) -0.12212(12) 0.0465(3) Uani d 1
H H12 0.3945 0.9324 -0.1271 0.056 Uiso calc 1
N N1 0.44994(9) 0.74494(15) 0.05856(9) 0.0433(2) Uani d 1
N N2 0.04664(11) 0.8230(2) -0.29732(11) 0.0588(3) Uani d 1
O O1 0.04178(11) 0.9053(2) -0.38389(10) 0.0808(4) Uani d 1
O O2 -0.03044(10) 0.7504(3) -0.28855(12) 0.0869(4) Uani d 1
S S1 0.67202(2) 0.63767(4) 0.22616(3) 0.04172(10) 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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1A C1 H1B 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C2 C1 H1A 109.5
C2 C1 H1B 109.5
C2 C1 H1C 109.5
C1 C2 S1 121.10(11)
C3 C2 C1 127.90(13)
C3 C2 S1 111.01(10)
C2 C3 H3 123.3
C2 C3 C4 113.39(12)
C4 C3 H3 123.3
C3 C4 H4 123.6
C5 C4 C3 112.81(12)
C5 C4 H4 123.6
C4 C5 C6 127.64(12)
C4 C5 S1 110.91(10)
C6 C5 S1 121.45(9)
C5 C6 H6 119.1
N1 C6 C5 121.75(11)
N1 C6 H6 119.1
C8 C7 C12 119.33(11)
C8 C7 N1 122.47(11)
C12 C7 N1 118.10(11)
C7 C8 H8 119.7
C9 C8 C7 120.66(12)
C9 C8 H8 119.7
C8 C9 H9 120.7
C10 C9 C8 118.54(12)
C10 C9 H9 120.7
C9 C10 C11 122.24(12)
C9 C10 N2 119.02(13)
C11 C10 N2 118.73(13)
C10 C11 H11 120.6
C12 C11 C10 118.84(12)
C12 C11 H11 120.6
C7 C12 H12 119.8
C11 C12 C7 120.37(13)
C11 C12 H12 119.8
C6 N1 C7 119.28(11)
O1 N2 C10 118.28(15)
O2 N2 C10 118.78(14)
O2 N2 O1 122.91(14)
C2 S1 C5 91.88(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C1 C2 1.4935(19)
C2 C3 1.3616(19)
C2 S1 1.7222(13)
C3 H3 0.9300
C3 C4 1.405(2)
C4 H4 0.9300
C4 C5 1.3698(17)
C5 C6 1.4429(17)
C5 S1 1.7246(12)
C6 H6 0.9300
C6 N1 1.2760(17)
C7 C8 1.3901(18)
C7 C12 1.3977(17)
C7 N1 1.4045(16)
C8 H8 0.9300
C8 C9 1.3801(18)
C9 H9 0.9300
C9 C10 1.3788(19)
C10 C11 1.379(2)
C10 N2 1.4612(18)
C11 H11 0.9300
C11 C12 1.376(2)
C12 H12 0.9300
N2 O1 1.2247(19)
N2 O2 1.218(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132775333
