##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(E)-4-Methyl-N-[(5-nitrothiophen-2-yl)methylidene]aniline
;
_chemical_name_common     ?
_chemical_formula_moiety     'C12 H10 N2 O2 S'
_chemical_formula_sum     'C12 H10 N2 O2 S'
_chemical_formula_iupac     'C12 H10 N2 O2 S'
_chemical_formula_weight     246.28
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     4.7661(4)
_cell_length_b     22.8201(18)
_cell_length_c     10.7793(7)
_cell_angle_alpha     90.00
_cell_angle_beta     92.704(7)
_cell_angle_gamma     90.00
_cell_volume     1171.08(15)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1442
_cell_measurement_theta_min     3.2725
_cell_measurement_theta_max     27.6413
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     brown
_exptl_crystal_size_max     0.17
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.397
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     512
_exptl_absorpt_coefficient_mu     0.264
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_absorpt_correction_T_min     0.77137
_exptl_absorpt_correction_T_max     1.00000
_exptl_special_details     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'Oxford Diffraction SuperNova  Eos'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     16.0454
_diffrn_reflns_number     3997
_diffrn_reflns_av_R_equivalents     0.0635
_diffrn_reflns_av_sigmaI/netI     0.0834
_diffrn_reflns_theta_min     3.28
_diffrn_reflns_theta_max     25.97
_diffrn_reflns_theta_full     25.97
_diffrn_measured_fraction_theta_max     0.963
_diffrn_measured_fraction_theta_full     0.963
_diffrn_reflns_limit_h_min     -5
_diffrn_reflns_limit_h_max     5
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     26
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2211
_reflns_number_gt     1549
_reflns_threshold_expression     >2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0929
_refine_ls_R_factor_gt     0.0628
_refine_ls_wR_factor_gt     0.1505
_refine_ls_wR_factor_ref     0.1768
_refine_ls_goodness_of_fit_ref     1.053
_refine_ls_restrained_S_all     1.053
_refine_ls_number_reflns     2211
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0778P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.263
_refine_diff_density_min     -0.282
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_cell_refinement     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_reduction     'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_structure_solution
                        'WinGX (Farrugia, 1997) and SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_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)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    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 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    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_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
    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_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 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) ?
data_New_Global_Publ_Block
_journal_date_recd_electronic     2012-05-29
_journal_date_accepted     2012-06-08
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      7
_journal_page_first     o2116
_journal_page_last     o2116
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536812026062
_journal_coeditor_code     NC2283
_publ_contact_author_name     'Ümit Ceylan'
_publ_contact_author_address
;
Department of Physics
Faculty of Arts and Sciences
Ondokuz Mayıs University
55139-Samsun
Turkey
;
_publ_contact_author_email     'uceylan@omu.edu.tr'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
(E)-4-Methyl-N-[(5-nitrothiophen-2-yl)methylidene]aniline
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Ceylan, Ümit' ?
;
Department of Physics
Faculty of Arts and Sciences
Ondokuz Mayıs University
55139 Samsun
Turkey
;
    'Gümüş, Sümeyye' .
;
Department of Chemistry
Faculty of Arts and Sciences
Ondokuz Mayıs University
55139 Samsun
Turkey
;
    'Ağar, Erbil' .
;
Department of Chemistry
Faculty of Arts and Sciences
Ondokuz Mayıs University
55139 Samsun
Turkey
;
    'Soylu, Mustafa Serkan' .
;
Department of Physics
Faculty of Arts and Sciences
Giresun University
28100 Giresun
Turkey
;
_publ_section_synopsis     .
