#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/55/2235558.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_2235558
loop_
_publ_author_name
'Ceylan, Ümit'
'Gümüş, Sümeyye'
'Ağar, Erbil'
'Soylu, Mustafa Serkan'
_publ_section_title
;
 (E)-4-Methyl-N-[(5-nitrothiophen-2-yl)methylidene]aniline
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2116
_journal_paper_doi               10.1107/S1600536812026062
_journal_volume                  68
_journal_year                    2012
_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_name_systematic
;
(E)-4-Methyl-N-[(5-nitrothiophen-2-yl)methylidene]aniline
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.704(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7661(4)
_cell_length_b                   22.8201(18)
_cell_length_c                   10.7793(7)
_cell_measurement_reflns_used    1442
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.6413
_cell_measurement_theta_min      3.2725
_cell_volume                     1171.08(15)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al. 2009) and ORTEP-3 for Windows (Farrugia,
1997);
;
_computing_publication_material
;OLEX2 (Dolomanov et al. 2009), WinGX (Farrugia, 1999) and
PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
'WinGX (Farrugia, 1997) and SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 16.0454
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova  Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0834
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3997
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         3.28
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0628
_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)+(0.0778P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1768
_reflns_number_gt                1549
_reflns_number_total             2211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nc2283.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2235558
_cod_database_fobs_code          2235558
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
_atom_site_symmetry_multiplicity
C C1 1.8771(9) 0.51221(18) 0.2226(4) 0.0792(14) Uani d . 1 1
H H1A 2.0022 0.5083 0.1558 0.119 Uiso calc R 1 1
H H1B 1.9835 0.5118 0.3005 0.119 Uiso calc R 1 1
H H1C 1.7765 0.5485 0.2141 0.119 Uiso calc R 1 1
C C2 1.6709(7) 0.46177(17) 0.2185(4) 0.0576(11) Uani d . 1 1
C C3 1.5819(8) 0.43632(17) 0.1076(4) 0.0586(11) Uani d . 1 1
H H3 1.6539 0.4500 0.0343 0.070 Uiso calc R 1 1
C C4 1.3897(7) 0.39125(16) 0.1021(3) 0.0498(9) Uani d . 1 1
H H4 1.3321 0.3754 0.0256 0.060 Uiso calc R 1 1
C C5 1.2814(7) 0.36934(15) 0.2103(3) 0.0409(8) Uani d . 1 1
C C6 1.3763(8) 0.39378(17) 0.3217(3) 0.0498(9) Uani d . 1 1
H H6 1.3103 0.3794 0.3956 0.060 Uiso calc R 1 1
C C7 1.5673(8) 0.43920(17) 0.3253(4) 0.0623(11) Uani d . 1 1
H H7 1.6273 0.4549 0.4017 0.075 Uiso calc R 1 1
C C8 0.9566(7) 0.30543(15) 0.1167(3) 0.0436(8) Uani d . 1 1
H H8 0.9950 0.3238 0.0424 0.052 Uiso calc R 1 1
C C9 0.7549(7) 0.25849(15) 0.1140(3) 0.0407(8) Uani d . 1 1
C C10 0.6197(7) 0.23554(16) 0.0104(3) 0.0501(10) Uani d . 1 1
H H10 0.6498 0.2486 -0.0696 0.060 Uiso calc R 1 1
C C11 0.4313(7) 0.19048(16) 0.0363(3) 0.0479(9) Uani d . 1 1
H H11 0.3243 0.1699 -0.0236 0.057 Uiso calc R 1 1
C C12 0.4260(7) 0.18089(14) 0.1598(3) 0.0379(8) Uani d . 1 1
N N1 1.0843(6) 0.32285(12) 0.2158(2) 0.0413(7) Uani d . 1 1
N N2 0.2502(6) 0.13966(14) 0.2189(3) 0.0488(8) Uani d . 1 1
O O1 0.2643(6) 0.13733(12) 0.3329(2) 0.0663(8) Uani d . 1 1
O O2 0.0953(6) 0.10886(13) 0.1531(3) 0.0692(8) Uani d . 1 1
S S1 0.64676(18) 0.22535(4) 0.24745(7) 0.0417(3) Uani d . 1 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
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
C7 C2 C3 117.4(4)
C7 C2 C1 121.3(4)
C3 C2 C1 121.3(4)
C4 C3 C2 122.0(4)
C4 C3 H3 119.0
C2 C3 H3 119.0
C3 C4 C5 120.3(4)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 117.7(3)
C6 C5 N1 117.1(3)
C4 C5 N1 125.2(3)
C7 C6 C5 121.1(3)
C7 C6 H6 119.4
C5 C6 H6 119.4
C2 C7 C6 121.4(4)
C2 C7 H7 119.3
C6 C7 H7 119.3
N1 C8 C9 123.0(3)
N1 C8 H8 118.5
C9 C8 H8 118.5
C10 C9 C8 126.2(3)
C10 C9 S1 111.4(3)
C8 C9 S1 122.4(2)
C9 C10 C11 113.6(3)
C9 C10 H10 123.2
C11 C10 H10 123.2
C12 C11 C10 110.9(3)
C12 C11 H11 124.6
C10 C11 H11 124.6
C11 C12 N2 125.8(3)
C11 C12 S1 114.1(3)
N2 C12 S1 120.1(2)
C8 N1 C5 119.4(3)
O2 N2 O1 124.0(3)
O2 N2 C12 118.1(3)
O1 N2 C12 118.0(3)
C12 S1 C9 89.98(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.513(5)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C7 1.374(5)
C2 C3 1.378(5)
C3 C4 1.377(5)
C3 H3 0.9300
C4 C5 1.391(4)
C4 H4 0.9300
C5 C6 1.381(5)
C5 N1 1.420(4)
C6 C7 1.379(5)
C6 H6 0.9300
C7 H7 0.9300
C8 N1 1.269(4)
C8 C9 1.439(5)
C8 H8 0.9300
C9 C10 1.366(4)
C9 S1 1.725(3)
C10 C11 1.402(4)
C10 H10 0.9300
C11 C12 1.351(4)
C11 H11 0.9300
C12 N2 1.430(4)
C12 S1 1.713(3)
N2 O2 1.222(4)
N2 O1 1.228(4)
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
C7 C2 C3 C4 2.1(6)
C1 C2 C3 C4 -178.5(3)
C2 C3 C4 C5 -0.9(6)
C3 C4 C5 C6 -0.9(5)
C3 C4 C5 N1 -179.5(3)
C4 C5 C6 C7 1.4(5)
N1 C5 C6 C7 -179.9(3)
C3 C2 C7 C6 -1.6(6)
C1 C2 C7 C6 179.1(4)
C5 C6 C7 C2 -0.2(6)
N1 C8 C9 C10 -176.6(3)
N1 C8 C9 S1 5.4(5)
C8 C9 C10 C11 -179.2(3)
S1 C9 C10 C11 -1.0(4)
C9 C10 C11 C12 0.8(4)
C10 C11 C12 N2 177.6(3)
C10 C11 C12 S1 -0.2(4)
C9 C8 N1 C5 179.7(3)
C6 C5 N1 C8 168.5(3)
C4 C5 N1 C8 -12.8(5)
C11 C12 N2 O2 2.2(5)
S1 C12 N2 O2 179.8(3)
C11 C12 N2 O1 -177.9(3)
S1 C12 N2 O1 -0.2(4)
C11 C12 S1 C9 -0.3(3)
N2 C12 S1 C9 -178.2(3)
C10 C9 S1 C12 0.7(3)
C8 C9 S1 C12 179.0(3)
