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#$Date: 2021-01-20 08:23:19 +0200 (Wed, 20 Jan 2021) $
#$Revision: 261085 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243730.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_2243730
loop_
_publ_author_name
'Kansiz, Sevgi'
'Dege, Necmi'
'Ozturk, Seyhan'
'Akdemir, Nesuhi'
'Tarcan, Erdoğan'
'Arslanhan, Ali'
'Saif, Eiad'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 2-methyl-3-nitro-N-[(E)-(5-nitrothiophen-2-yl)methylidene]aniline
;
_journal_coeditor_code           YK2142
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              138
_journal_page_last               141
_journal_paper_doi               10.1107/S2056989021000529
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C12 H9 N3 O4 S'
_chemical_formula_sum            'C12 H9 N3 O4 S'
_chemical_formula_weight         291.28
_chemical_name_systematic
;
2-Methyl-3-nitro-N-[(E)-(5-nitrothiophen-2-yl)methylidene]aniline
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1335(4)
_cell_length_b                   11.7297(6)
_cell_length_c                   15.4593(7)
_cell_measurement_reflns_used    6261
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.85
_cell_measurement_theta_min      2.18
_cell_volume                     1293.54(11)
_computing_cell_refinement
;
X-AREA(Stoe & Cie, 2002)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED32 (Stoe & Cie, 2002)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2017/1 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6707
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.475
_diffrn_reflns_theta_min         2.179
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_T_max  0.9655
_exptl_absorpt_correction_T_min  0.8388
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       stick
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.194
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.59(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0630P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                2258
_reflns_number_total             3930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2142sup1.cif
_cod_data_source_block           I
_cod_database_code               2243730
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.63801(15) 0.83820(8) 0.62698(6) 0.0504(3) Uani d 1 . .
N N2 0.6540(5) 0.6808(2) 0.47460(18) 0.0437(7) Uani d 1 . .
N N1 0.7061(6) 0.2794(3) 0.3994(3) 0.0637(10) Uani d 1 . .
O O2 0.8371(6) 0.2537(3) 0.4460(2) 0.0886(11) Uani d 1 . .
O O1 0.5937(6) 0.2119(3) 0.3708(3) 0.0988(13) Uani d 1 . .
C C8 0.7015(6) 0.7831(3) 0.4567(2) 0.0432(8) Uani d 1 . .
C C7 0.6589(5) 0.5963(3) 0.4097(2) 0.0397(7) Uani d 1 . .
C C9 0.6899(5) 0.8708(3) 0.5213(2) 0.0431(8) Uani d 1 . .
C C6 0.6287(6) 0.6186(3) 0.3229(2) 0.0487(9) Uani d 1 . .
H H6 0.610040 0.693392 0.304891 0.058 Uiso calc 1 . .
C C3 0.6828(5) 0.4000(3) 0.3749(3) 0.0474(8) Uani d 1 . .
N N3 0.6315(7) 1.0145(4) 0.7400(3) 0.0756(12) Uani d 1 . .
C C2 0.6860(5) 0.4834(3) 0.4389(2) 0.0423(8) Uani d 1 . .
C C4 0.6524(7) 0.4210(3) 0.2888(2) 0.0549(9) Uani d 1 . .
H H4 0.649811 0.361601 0.249035 0.066 Uiso calc 1 . .
O O3 0.5983(7) 0.9420(5) 0.7941(2) 0.1054(15) Uani d 1 . .
C C12 0.6570(6) 0.9799(3) 0.6526(2) 0.0537(10) Uani d 1 . .
C C11 0.7002(6) 1.0482(3) 0.5853(3) 0.0575(11) Uani d 1 . .
H H11 0.714508 1.126873 0.589073 0.069 Uiso calc 1 . .
O O4 0.6437(7) 1.1168(4) 0.7564(3) 0.1149(15) Uani d 1 . .
C C10 0.7204(6) 0.9856(3) 0.5095(3) 0.0520(10) Uani d 1 . .
H H10 0.751275 1.017854 0.456431 0.062 Uiso calc 1 . .
C C1 0.7131(7) 0.4585(4) 0.5333(3) 0.0559(10) Uani d 1 . .
H H1A 0.710488 0.528510 0.565450 0.084 Uiso calc 1 . .
H H1B 0.614362 0.409413 0.553194 0.084 Uiso calc 1 . .
H H1C 0.831809 0.421538 0.541751 0.084 Uiso calc 1 . .
C C5 0.6258(7) 0.5321(4) 0.2626(2) 0.0573(10) Uani d 1 . .
H H5 0.606041 0.548561 0.204434 0.069 Uiso calc 1 . .
H H8 0.747(5) 0.807(3) 0.403(2) 0.034(9) Uiso 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C12 S1 C9 . . 89.25(18) ?
C8 N2 C7 . . 120.0(3) ?
O1 N1 O2 . . 124.3(4) ?
O1 N1 C3 . . 117.3(4) ?
O2 N1 C3 . . 118.4(4) ?
N2 C8 C9 . . 120.5(3) ?
N2 C8 H8 . . 124(2) ?
C9 C8 H8 . . 115(2) ?
C6 C7 N2 . . 123.5(3) ?
C6 C7 C2 . . 120.6(3) ?
N2 C7 C2 . . 115.8(3) ?
C10 C9 C8 . . 126.9(4) ?
C10 C9 S1 . . 112.2(3) ?
C8 C9 S1 . . 120.9(3) ?
C5 C6 C7 . . 121.3(3) ?
C5 C6 H6 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
C4 C3 C2 . . 124.5(3) ?
C4 C3 N1 . . 116.1(3) ?
C2 C3 N1 . . 119.4(4) ?
O3 N3 O4 . . 123.7(5) ?
O3 N3 C12 . . 118.6(4) ?
O4 N3 C12 . . 117.7(5) ?
C3 C2 C7 . . 115.4(3) ?
C3 C2 C1 . . 123.8(3) ?
C7 C2 C1 . . 120.8(3) ?
C3 C4 C5 . . 118.6(3) ?
C3 C4 H4 . . 120.7 ?
C5 C4 H4 . . 120.7 ?
C11 C12 N3 . . 126.4(4) ?
C11 C12 S1 . . 114.6(3) ?
N3 C12 S1 . . 119.0(3) ?
C12 C11 C10 . . 111.1(4) ?
C12 C11 H11 . . 124.5 ?
C10 C11 H11 . . 124.5 ?
C9 C10 C11 . . 112.9(4) ?
C9 C10 H10 . . 123.5 ?
C11 C10 H10 . . 123.6 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C4 C5 C6 . . 119.7(4) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
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 C12 . 1.714(4) y
S1 C9 . 1.718(4) y
N2 C8 . 1.277(4) y
N2 C7 . 1.411(4) y
N1 O1 . 1.211(5) y
N1 O2 . 1.218(5) y
N1 C3 . 1.474(5) y
C8 C9 . 1.435(5) ?
C8 H8 . 0.93(4) ?
C7 C6 . 1.384(5) ?
C7 C2 . 1.412(5) ?
C9 C10 . 1.376(5) ?
C6 C5 . 1.378(5) ?
C6 H6 . 0.9300 ?
C3 C4 . 1.371(5) ?
C3 C2 . 1.392(5) ?
N3 O3 . 1.216(6) y
N3 O4 . 1.230(6) y
N3 C12 . 1.423(5) y
C2 C1 . 1.501(5) ?
C4 C5 . 1.377(6) ?
C4 H4 . 0.9300 ?
C12 C11 . 1.349(6) ?
C11 C10 . 1.391(6) ?
C11 H11 . 0.9300 ?
C10 H10 . 0.9300 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C5 H5 . 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
C8 H8 O4 2_674 0.93(4) 2.56(4) 3.492(5) 176(3) 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N2 C8 C9 . . . . 177.5(3) ?
C8 N2 C7 C6 . . . . -30.4(6) ?
C8 N2 C7 C2 . . . . 153.2(4) ?
N2 C8 C9 C10 . . . . -173.9(4) ?
N2 C8 C9 S1 . . . . 7.5(5) ?
C12 S1 C9 C10 . . . . 0.4(3) ?
C12 S1 C9 C8 . . . . 179.2(3) ?
N2 C7 C6 C5 . . . . -176.7(4) ?
C2 C7 C6 C5 . . . . -0.5(7) ?
O1 N1 C3 C4 . . . . -47.0(6) ?
O2 N1 C3 C4 . . . . 132.2(4) ?
O1 N1 C3 C2 . . . . 130.8(4) ?
O2 N1 C3 C2 . . . . -50.0(6) ?
C4 C3 C2 C7 . . . . -1.2(6) ?
N1 C3 C2 C7 . . . . -178.8(3) ?
C4 C3 C2 C1 . . . . 177.9(4) ?
N1 C3 C2 C1 . . . . 0.3(6) ?
C6 C7 C2 C3 . . . . 0.9(6) ?
N2 C7 C2 C3 . . . . 177.4(3) ?
C6 C7 C2 C1 . . . . -178.2(4) ?
N2 C7 C2 C1 . . . . -1.7(6) ?
C2 C3 C4 C5 . . . . 1.0(7) ?
N1 C3 C4 C5 . . . . 178.7(4) ?
O3 N3 C12 C11 . . . . -177.8(5) ?
O4 N3 C12 C11 . . . . 2.5(8) ?
O3 N3 C12 S1 . . . . 0.6(7) ?
O4 N3 C12 S1 . . . . -179.2(4) ?
C9 S1 C12 C11 . . . . 0.0(4) ?
C9 S1 C12 N3 . . . . -178.6(4) ?
N3 C12 C11 C10 . . . . 178.1(4) ?
S1 C12 C11 C10 . . . . -0.3(5) ?
C8 C9 C10 C11 . . . . -179.3(4) ?
S1 C9 C10 C11 . . . . -0.7(4) ?
C12 C11 C10 C9 . . . . 0.6(5) ?
C3 C4 C5 C6 . . . . -0.5(7) ?
C7 C6 C5 C4 . . . . 0.3(7) ?

_cod_database_fobs_code 2243730
