#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/80/2228035.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228035
loop_
_publ_author_name
'Mendonça Junior, Francisco J.B.'
'do Lima, Maria'
'Galdino, Suely L.'
'Pitta, Ivan R.'
'de Simone, Carlos A.'
_publ_section_title
;
 2-(2-Nitroanilino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile
;
_journal_coeditor_code           TK2704
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2543
_journal_paper_doi               10.1107/S1600536810035439
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 N3 O2 S'
_chemical_formula_moiety         'C15 H13 N3 O2 S'
_chemical_formula_sum            'C15 H13 N3 O2 S'
_chemical_formula_weight         299.34
_chemical_name_systematic
;
2-(2-Nitroanilino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile
;
_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                 106.794(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2764(4)
_cell_length_b                   13.4447(7)
_cell_length_c                   8.2237(4)
_cell_measurement_reflns_used    4953
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1405.30(11)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and SCALEPACK'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD rotation images,thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'Enraf Nonius FR590'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9590
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.171
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.382
_refine_ls_extinction_coef       0.133(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0572
_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)+(0.1015P)²+0.2662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1741
_reflns_number_gt                2351
_reflns_number_total             3241
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            tk2704.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228035
_cod_database_fobs_code          2228035
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.22931(15) -0.11377(16) -0.8690(3) 0.0489(5) Uani d . 1 . .
C C2 -0.17013(15) -0.19140(16) -0.7859(2) 0.0470(5) Uani d . 1 . .
C C3 -0.06070(15) -0.16847(17) -0.7171(3) 0.0494(5) Uani d . 1 . .
C C4 0.02377(17) -0.2391(2) -0.6205(3) 0.0620(6) Uani d . 1 . .
H H4A 0.0009 -0.2717 -0.5322 0.074 Uiso calc R 1 . .
H H4B 0.0352 -0.2898 -0.6972 0.074 Uiso calc R 1 . .
C C5 0.1254(2) -0.1846(3) -0.5417(5) 0.1058(12) Uani d . 1 . .
H H5A 0.1231 -0.1586 -0.4328 0.127 Uiso calc R 1 . .
H H5B 0.1823 -0.2325 -0.5196 0.127 Uiso calc R 1 . .
C C6 0.1505(2) -0.1041(3) -0.6378(6) 0.1056(13) Uani d . 1 . .
H H6A 0.1667 -0.1319 -0.7362 0.127 Uiso calc R 1 . .
H H6B 0.2138 -0.0720 -0.5686 0.127 Uiso calc R 1 . .
C C7 0.06661(19) -0.0251(2) -0.6990(4) 0.0700(7) Uani d . 1 . .
H H7A 0.0705 0.0225 -0.6088 0.084 Uiso calc R 1 . .
H H7B 0.0783 0.0102 -0.7948 0.084 Uiso calc R 1 . .
C C8 -0.04015(15) -0.07297(18) -0.7510(3) 0.0540(5) Uani d . 1 . .
C C9 -0.41366(15) -0.11662(14) -0.8689(3) 0.0449(5) Uani d . 1 . .
C C10 -0.38494(18) -0.10942(18) -0.6915(3) 0.0560(6) Uani d . 1 . .
H H10 -0.3142 -0.1031 -0.6314 0.067 Uiso calc R 1 . .
C C11 -0.4588(2) -0.1114(2) -0.6043(3) 0.0649(6) Uani d . 1 . .
H H11 -0.4374 -0.1062 -0.4865 0.078 Uiso calc R 1 . .
C C12 -0.5649(2) -0.1210(2) -0.6897(4) 0.0703(7) Uani d . 1 . .
H H12 -0.6145 -0.1229 -0.6298 0.084 Uiso calc R 1 . .
C C13 -0.59545(18) -0.12779(18) -0.8620(4) 0.0622(6) Uani d . 1 . .
H H13 -0.6665 -0.1338 -0.9202 0.075 Uiso calc R 1 . .
C C14 -0.52138(16) -0.12570(15) -0.9526(3) 0.0486(5) Uani d . 1 . .
C C15 -0.21465(15) -0.28666(18) -0.7727(3) 0.0519(5) Uani d . 1 . .
N N1 -0.25004(17) -0.36281(16) -0.7606(3) 0.0673(6) Uani d . 1 . .
N N2 -0.33714(13) -0.11309(15) -0.9523(2) 0.0524(5) Uani d . 1 . .
H H2 -0.3569 -0.1103 -1.0614 0.063 Uiso calc R 1 . .
N N3 -0.56173(15) -0.13233(14) -1.1361(3) 0.0572(5) Uani d . 1 . .
O O1 -0.49971(14) -0.12880(15) -1.2218(2) 0.0713(5) Uani d . 1 . .
O O2 -0.65641(14) -0.14080(17) -1.2012(3) 0.0866(6) Uani d . 1 . .
S S1 -0.15219(4) -0.01029(5) -0.86321(8) 0.0610(3) Uani 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
C2 C1 N2 . . 127.62(19) ?
C2 C1 S1 . . 110.65(15) ?
N2 C1 S1 . . 121.72(16) ?
C1 C2 C15 . . 122.20(18) ?
C1 C2 C3 . . 113.87(19) ?
C15 C2 C3 . . 123.92(19) ?
C8 C3 C2 . . 111.30(19) ?
C8 C3 C4 . . 122.69(19) ?
C2 C3 C4 . . 126.0(2) ?
C5 C4 C3 . . 111.0(2) ?
C5 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
C5 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C6 C5 C4 . . 116.8(3) ?
C6 C5 H5A . . 108.1 ?
C4 C5 H5A . . 108.1 ?
C6 C5 H5B . . 108.1 ?
C4 C5 H5B . . 108.1 ?
H5A C5 H5B . . 107.3 ?
C5 C6 C7 . . 116.4(3) ?
C5 C6 H6A . . 108.2 ?
C7 C6 H6A . . 108.2 ?
C5 C6 H6B . . 108.2 ?
C7 C6 H6B . . 108.2 ?
H6A C6 H6B . . 107.3 ?
C8 C7 C6 . . 109.7(2) ?
C8 C7 H7A . . 109.7 ?
C6 C7 H7A . . 109.7 ?
C8 C7 H7B . . 109.7 ?
C6 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
C3 C8 C7 . . 125.1(2) ?
C3 C8 S1 . . 112.21(15) ?
C7 C8 S1 . . 122.6(2) ?
N2 C9 C10 . . 119.80(18) ?
N2 C9 C14 . . 123.48(19) ?
C10 C9 C14 . . 116.71(19) ?
C11 C10 C9 . . 121.5(2) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C10 C11 C12 . . 120.8(2) ?
C10 C11 H11 . . 119.6 ?
C12 C11 H11 . . 119.6 ?
C13 C12 C11 . . 119.2(2) ?
C13 C12 H12 . . 120.4 ?
C11 C12 H12 . . 120.4 ?
C12 C13 C14 . . 120.7(2) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C13 C14 C9 . . 121.1(2) ?
C13 C14 N3 . . 116.7(2) ?
C9 C14 N3 . . 122.25(19) ?
N1 C15 C2 . . 179.4(2) ?
C9 N2 C1 . . 123.57(17) ?
C9 N2 H2 . . 118.2 ?
C1 N2 H2 . . 118.2 ?
O2 N3 O1 . . 121.8(2) ?
O2 N3 C14 . . 119.0(2) ?
O1 N3 C14 . . 119.12(18) ?
C1 S1 C8 . . 91.95(10) ?
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 . 1.365(3) ?
C1 N2 . 1.397(2) ?
C1 S1 . 1.720(2) ?
C2 C15 . 1.428(3) ?
C2 C3 . 1.432(3) ?
C3 C8 . 1.358(3) ?
C3 C4 . 1.508(3) ?
C4 C5 . 1.507(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.436(5) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.516(4) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.502(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 S1 . 1.727(2) ?
C9 N2 . 1.381(2) ?
C9 C10 . 1.401(3) ?
C9 C14 . 1.402(3) ?
C10 C11 . 1.372(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.386(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.360(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.395(3) ?
C13 H13 . 0.9300 ?
C14 N3 . 1.451(3) ?
C15 N1 . 1.143(3) ?
N2 H2 . 0.8600 ?
N3 O2 . 1.221(3) ?
N3 O1 . 1.230(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
_geom_hbond_publ_flag
N2 H2 N1 4_555 0.86 2.48 3.093(3) 129 yes
C11 H11 O1 1_556 0.93 2.56 3.351(3) 143 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3199115
