#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/15/2231583.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_2231583
loop_
_publ_author_name
'Cai, Mingjian'
'Wang, Xiuge'
'Sun, Tao'
_publ_section_title
;
 4-Methyl-N-[(5-nitrothiophen-2-yl)methylidene]aniline
;
_journal_coeditor_code           LD2020
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2218
_journal_paper_doi               10.1107/S1600536811030297
_journal_volume                  67
_journal_year                    2011
_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
;
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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.566(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7606(4)
_cell_length_b                   22.415(2)
_cell_length_c                   10.7008(15)
_cell_measurement_reflns_used    4173
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.8
_cell_volume                     1140.7(2)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2002)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2002)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 2009)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.22
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14437
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         1.82
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.9679
_exptl_absorpt_correction_T_min  0.9473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.273
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0397
_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)+(0.0505P)²+0.1298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                2325
_reflns_number_total             2699
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ld2020.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2231583
_cod_database_fobs_code          2231583
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
S S1 0.12948(8) 0.223694(17) 0.24141(3) 0.01725(12) Uani d . 1 1
O O1 -0.4301(2) 0.10562(5) 0.14443(11) 0.0279(3) Uani d . 1 1
O O2 -0.2638(2) 0.13512(5) 0.32720(10) 0.0257(3) Uani d . 1 1
N N1 0.5743(3) 0.32247(6) 0.21001(11) 0.0170(3) Uani d . 1 1
N N2 -0.2748(3) 0.13695(6) 0.21144(12) 0.0200(3) Uani d . 1 1
C C1 1.3858(3) 0.51381(7) 0.21589(19) 0.0294(4) Uani d . 1 1
H H1A 1.5510 0.5020 0.1704 0.044 Uiso calc R 1 1
H H1B 1.4432 0.5230 0.3028 0.044 Uiso calc R 1 1
H H1C 1.2998 0.5492 0.1763 0.044 Uiso calc R 1 1
C C2 1.1750(3) 0.46324(7) 0.21303(16) 0.0220(3) Uani d . 1 1
C C3 1.0879(3) 0.43701(7) 0.10002(15) 0.0223(3) Uani d . 1 1
H H3 1.1645 0.4507 0.0248 0.027 Uiso calc R 1 1
C C4 0.8909(3) 0.39115(7) 0.09487(14) 0.0197(3) Uani d . 1 1
H H4 0.8337 0.3742 0.0164 0.024 Uiso calc R 1 1
C C5 0.7759(3) 0.36966(7) 0.20461(14) 0.0169(3) Uani d . 1 1
C C6 0.8680(3) 0.39494(7) 0.31778(14) 0.0199(3) Uani d . 1 1
H H6 0.7965 0.3804 0.3935 0.024 Uiso calc R 1 1
C C7 1.0628(3) 0.44113(7) 0.32203(16) 0.0233(4) Uani d . 1 1
H H7 1.1207 0.4579 0.4005 0.028 Uiso calc R 1 1
C C8 0.4454(3) 0.30556(7) 0.10888(14) 0.0189(3) Uani d . 1 1
H H8 0.4859 0.3248 0.0327 0.023 Uiso calc R 1 1
C C9 0.2385(3) 0.25772(7) 0.10682(14) 0.0173(3) Uani d . 1 1
C C10 0.1041(3) 0.23474(7) 0.00118(14) 0.0208(3) Uani d . 1 1
H H10 0.1382 0.2483 -0.0809 0.025 Uiso calc R 1 1
C C11 -0.0895(3) 0.18913(7) 0.02644(14) 0.0194(3) Uani d . 1 1
H H11 -0.2003 0.1683 -0.0354 0.023 Uiso calc R 1 1
C C12 -0.0955(3) 0.17906(7) 0.15201(14) 0.0166(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
C12 S1 C9 89.77(7)
C8 N1 C5 118.86(13)
O1 N2 O2 124.27(13)
O1 N2 C12 118.08(13)
O2 N2 C12 117.65(13)
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
C3 C2 C7 117.78(14)
C3 C2 C1 120.39(15)
C7 C2 C1 121.84(15)
C4 C3 C2 121.40(15)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C5 120.55(14)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 118.01(14)
C6 C5 N1 116.87(13)
C4 C5 N1 125.10(13)
C7 C6 C5 121.08(15)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C2 121.15(15)
C6 C7 H7 119.4
C2 C7 H7 119.4
N1 C8 C9 122.04(14)
N1 C8 H8 119.0
C9 C8 H8 119.0
C10 C9 C8 125.35(14)
C10 C9 S1 111.94(12)
C8 C9 S1 122.70(11)
C9 C10 C11 113.47(14)
C9 C10 H10 123.3
C11 C10 H10 123.3
C12 C11 C10 110.57(14)
C12 C11 H11 124.7
C10 C11 H11 124.7
C11 C12 N2 125.62(14)
C11 C12 S1 114.25(12)
N2 C12 S1 120.10(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C12 1.7237(15)
S1 C9 1.7298(15)
O1 N2 1.2271(16)
O2 N2 1.2382(16)
N1 C8 1.277(2)
N1 C5 1.4312(19)
N2 C12 1.4398(19)
C1 C2 1.513(2)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.391(2)
C2 C7 1.395(2)
C3 C4 1.391(2)
C3 H3 0.9500
C4 C5 1.403(2)
C4 H4 0.9500
C5 C6 1.390(2)
C6 C7 1.389(2)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.456(2)
C8 H8 0.9500
C9 C10 1.374(2)
C10 C11 1.411(2)
C10 H10 0.9500
C11 C12 1.364(2)
C11 H11 0.9500
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 1.4(2)
C1 C2 C3 C4 -178.92(14)
C2 C3 C4 C5 -0.6(2)
C3 C4 C5 C6 -0.9(2)
C3 C4 C5 N1 -179.45(13)
C8 N1 C5 C6 167.13(14)
C8 N1 C5 C4 -14.3(2)
C4 C5 C6 C7 1.6(2)
N1 C5 C6 C7 -179.80(14)
C5 C6 C7 C2 -0.7(2)
C3 C2 C7 C6 -0.8(2)
C1 C2 C7 C6 179.55(14)
C5 N1 C8 C9 179.73(13)
N1 C8 C9 C10 -175.90(15)
N1 C8 C9 S1 5.1(2)
C12 S1 C9 C10 0.04(12)
C12 S1 C9 C8 179.15(13)
C8 C9 C10 C11 -179.16(14)
S1 C9 C10 C11 -0.08(17)
C9 C10 C11 C12 0.09(19)
C10 C11 C12 N2 178.01(13)
C10 C11 C12 S1 -0.06(17)
O1 N2 C12 C11 2.7(2)
O2 N2 C12 C11 -176.72(14)
O1 N2 C12 S1 -179.35(11)
O2 N2 C12 S1 1.25(18)
C9 S1 C12 C11 0.01(12)
C9 S1 C12 N2 -178.17(12)
