#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/07/2240765.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_2240765
loop_
_publ_author_name
'Koçak, Figen'
'Tanak, Hasan'
'Ağar, Erbil'
'Doğan, Onur Erman'
'Özdemir, Namık'
_publ_section_title
;
 Crystal structure of 2-{[(5-nitrothiophen-2-yl)methylidene]amino}phenol
;
_journal_coeditor_code           HB7421
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o418
_journal_paper_doi               10.1107/S2056989015009202
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C11 H8 N2 O3 S'
_chemical_formula_moiety         'C11 H8 N2 O3 S'
_chemical_formula_sum            'C11 H8 N2 O3 S'
_chemical_formula_weight         248.25
_chemical_name_systematic
;
2-{[(5-Nitrothiophen-2-yl)methylidene]amino}phenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.566(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.642(5)
_cell_length_b                   7.043(5)
_cell_length_c                   14.535(5)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.03
_cell_measurement_theta_min      1.92
_cell_volume                     1087.3(10)
_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
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_sigmaI/netI    0.1022
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7883
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.9649
_exptl_absorpt_correction_T_min  0.8772
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.886
_refine_diff_density_min         -0.447
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0635
_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)+(0.0675P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                1696
_reflns_number_total             2254
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7421sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2240765
_cod_database_fobs_code          2240765
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
_atom_site_symmetry_multiplicity
S S1 0.58190(4) 0.11508(6) 0.11107(3) 0.04605(16) Uani d 1 1
N N2 0.41409(13) 0.10939(19) 0.27382(9) 0.0449(3) Uani d 1 1
N N1 0.77113(14) 0.1231(2) -0.00532(10) 0.0532(4) Uani d 1 1
C C1 0.73710(15) 0.1181(2) 0.08813(11) 0.0453(4) Uani d 1 1
C C4 0.62428(15) 0.1069(2) 0.22648(11) 0.0460(4) Uani d 1 1
C C6 0.32806(15) 0.1149(2) 0.34380(11) 0.0438(4) Uani d 1 1
O O2 0.68543(14) 0.1159(2) -0.06611(9) 0.0733(4) Uani d 1 1
C C5 0.53109(16) 0.1040(3) 0.29481(12) 0.0496(4) Uani d 1 1
C C7 0.35846(18) 0.1360(3) 0.43745(12) 0.0512(4) Uani d 1 1
C C3 0.75216(17) 0.1053(3) 0.24363(13) 0.0625(5) Uani d 1 1
O O1 0.88152(13) 0.1329(3) -0.02073(10) 0.0807(5) Uani d 1 1
C C2 0.81816(17) 0.1119(3) 0.16344(13) 0.0581(5) Uani d 1 1
O O3 0.16507(15) 0.0835(3) 0.22346(11) 0.0904(6) Uani d 1 1
C C8 0.26579(19) 0.1470(3) 0.49960(13) 0.0574(5) Uani d 1 1
C C11 0.20103(17) 0.1045(3) 0.31379(13) 0.0584(5) Uani d 1 1
C C9 0.1415(2) 0.1387(3) 0.46888(15) 0.0665(5) Uani d 1 1
C C10 0.1095(2) 0.1179(4) 0.37699(17) 0.0748(6) Uani d 1 1
H H2 0.904(2) 0.113(3) 0.1586(14) 0.068(6) Uiso d 1 1
H H3 0.787(2) 0.107(3) 0.2986(17) 0.073(7) Uiso d 1 1
H H5 0.564(2) 0.096(3) 0.3560(17) 0.079(7) Uiso d 1 1
H H7 0.447(2) 0.150(3) 0.4606(13) 0.063(6) Uiso d 1 1
H H10 0.028(3) 0.112(4) 0.3543(19) 0.100(9) Uiso d 1 1
H H9 0.080(2) 0.151(3) 0.5109(16) 0.078(7) Uiso d 1 1
H H8 0.288(2) 0.167(3) 0.5609(16) 0.069(6) Uiso d 1 1
H H1 0.227(3) 0.069(4) 0.198(2) 0.097(10) Uiso 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
C1 S1 C4 89.58(8)
C5 N2 C6 120.03(15)
O1 N1 O2 123.60(15)
O1 N1 C1 118.92(15)
O2 N1 C1 117.48(15)
C2 C1 N1 125.76(16)
C2 C1 S1 114.73(13)
N1 C1 S1 119.50(13)
C3 C4 C5 126.26(16)
C3 C4 S1 112.18(13)
C5 C4 S1 121.56(13)
C7 C6 C11 118.31(16)
C7 C6 N2 126.03(16)
C11 C6 N2 115.62(15)
N2 C5 C4 122.75(16)
N2 C5 H5 122.4(15)
C4 C5 H5 114.9(15)
C8 C7 C6 121.03(18)
C8 C7 H7 118.6(12)
C6 C7 H7 120.3(12)
C4 C3 C2 113.16(17)
C4 C3 H3 122.7(16)
C2 C3 H3 124.1(16)
C1 C2 C3 110.35(16)
C1 C2 H2 121.6(13)
C3 C2 H2 128.0(13)
C11 O3 H1 106(2)
C9 C8 C7 119.92(19)
C9 C8 H8 120.7(14)
C7 C8 H8 119.3(14)
O3 C11 C10 118.94(18)
O3 C11 C6 121.26(17)
C10 C11 C6 119.80(18)
C10 C9 C8 120.01(18)
C10 C9 H9 120.7(14)
C8 C9 H9 119.3(14)
C9 C10 C11 120.9(2)
C9 C10 H10 122.2(18)
C11 C10 H10 116.8(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7054(18)
S1 C4 1.7107(18)
N2 C5 1.264(2)
N2 C6 1.411(2)
N1 O1 1.212(2)
N1 O2 1.231(2)
N1 C1 1.428(2)
C1 C2 1.352(3)
C4 C3 1.368(3)
C4 C5 1.447(2)
C6 C7 1.387(3)
C6 C11 1.396(2)
C5 H5 0.94(2)
C7 C8 1.380(3)
C7 H7 0.99(2)
C3 C2 1.399(3)
C3 H3 0.86(2)
C2 H2 0.92(2)
O3 C11 1.353(2)
O3 H1 0.78(3)
C8 C9 1.370(3)
C8 H8 0.92(2)
C11 C10 1.383(3)
C9 C10 1.366(3)
C9 H9 0.93(2)
C10 H10 0.91(3)
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
O3 H1 O2 3_655 0.78(3) 2.54(3) 3.192(3) 141(3)
O3 H1 N2 . 0.78(3) 2.23(3) 2.711(2) 121(3)
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
O1 N1 C1 C2 -4.2(3)
O2 N1 C1 C2 175.3(2)
O1 N1 C1 S1 177.06(14)
O2 N1 C1 S1 -3.4(2)
C4 S1 C1 C2 0.44(16)
C4 S1 C1 N1 179.27(14)
C1 S1 C4 C3 -0.44(16)
C1 S1 C4 C5 179.02(15)
C5 N2 C6 C7 7.5(3)
C5 N2 C6 C11 -174.84(17)
C6 N2 C5 C4 -177.11(16)
C3 C4 C5 N2 178.60(19)
S1 C4 C5 N2 -0.8(3)
C11 C6 C7 C8 -0.1(3)
N2 C6 C7 C8 177.44(17)
C5 C4 C3 C2 -179.07(19)
S1 C4 C3 C2 0.4(2)
N1 C1 C2 C3 -179.06(17)
S1 C1 C2 C3 -0.3(2)
C4 C3 C2 C1 0.0(3)
C6 C7 C8 C9 -0.6(3)
C7 C6 C11 O3 -179.9(2)
N2 C6 C11 O3 2.3(3)
C7 C6 C11 C10 0.9(3)
N2 C6 C11 C10 -176.96(19)
C7 C8 C9 C10 0.6(3)
C8 C9 C10 C11 0.1(4)
O3 C11 C10 C9 179.8(2)
C6 C11 C10 C9 -0.9(4)
