#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/60/2226097.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_2226097
loop_
_publ_author_name
'do Lima, Maria'
'Mendonça Junior, Francisco J. B.'
'Galdino, Suely L.'
'Pitta, Ivan R.'
'de Simone, Carlos A.'
_publ_section_title
;
 2-(2-Nitroanilino)-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carbonitrile
;
_journal_coeditor_code           DN2562
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1350
_journal_page_last               o1351
_journal_paper_doi               10.1107/S1600536810017149
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H15 N3 O2 S'
_chemical_formula_moiety         'C16 H15 N3 O2 S'
_chemical_formula_sum            'C16 H15 N3 O2 S'
_chemical_formula_weight         313.37
_chemical_name_systematic
;
2-(2-Nitroanilino)-5,6,7,8-tetrahydro-4H-cyclohepta[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                 97.571(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0273(3)
_cell_length_b                   14.4569(6)
_cell_length_c                   14.8867(7)
_cell_measurement_reflns_used    6392
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.733
_cell_measurement_theta_min      2.910
_cell_volume                     1499.20(11)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9360
_diffrn_reflns_theta_full        26.62
_diffrn_reflns_theta_max         26.62
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.269
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.305
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1026P)²+0.1476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1621
_reflns_number_gt                2452
_reflns_number_total             3147
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2562.cif
_cod_data_source_block           I
_cod_original_cell_volume        1499.18(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226097
_cod_database_fobs_code          2226097
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
S S1 0.29875(7) 0.33887(3) 0.05524(3) 0.0529(2) Uani d . 1 . .
O O1 0.1864(3) 0.64817(11) -0.14472(10) 0.0763(5) Uani d . 1 . .
O O2 0.1729(3) 0.78484(12) -0.09126(12) 0.0887(6) Uani d . 1 . .
N N1 0.2433(2) 0.50661(11) -0.03762(10) 0.0531(4) Uani d . 1 . .
H H1 0.2277 0.5305 -0.0910 0.064 Uiso calc R 1 . .
N N2 0.1906(2) 0.70191(13) -0.07994(12) 0.0594(4) Uani d . 1 . .
N N3 0.2128(4) 0.44432(17) -0.26828(13) 0.0871(7) Uani d . 1 . .
C C1 0.2620(2) 0.41167(13) -0.03697(12) 0.0474(4) Uani d . 1 . .
C C2 0.2544(3) 0.36042(14) -0.11578(12) 0.0501(4) Uani d . 1 . .
C C3 0.2772(3) 0.26261(14) -0.10156(13) 0.0527(5) Uani d . 1 . .
C C4 0.2731(4) 0.19525(16) -0.17935(14) 0.0673(6) Uani d . 1 . .
H H4A 0.4041 0.1775 -0.1850 0.081 Uiso calc R 1 . .
H H4B 0.2221 0.2269 -0.2348 0.081 Uiso calc R 1 . .
C C5 0.1554(3) 0.10721(16) -0.17147(15) 0.0688(6) Uani d . 1 . .
H H5A 0.0271 0.1251 -0.1609 0.083 Uiso calc R 1 . .
H H5B 0.1438 0.0750 -0.2291 0.083 Uiso calc R 1 . .
C C6 0.2345(4) 0.04019(15) -0.09784(16) 0.0707(6) Uani d . 1 . .
H H6A 0.3688 0.0293 -0.1031 0.085 Uiso calc R 1 . .
H H6B 0.1677 -0.0183 -0.1086 0.085 Uiso calc R 1 . .
C C7 0.2190(4) 0.07060(16) -0.00136(16) 0.0710(6) Uani d . 1 . .
H H7A 0.0872 0.0888 0.0021 0.085 Uiso calc R 1 . .
H H7B 0.2471 0.0179 0.0385 0.085 Uiso calc R 1 . .
C C8 0.3487(4) 0.14916(15) 0.03367(16) 0.0669(6) Uani d . 1 . .
H H8A 0.4798 0.1324 0.0270 0.080 Uiso calc R 1 . .
H H8B 0.3418 0.1564 0.0979 0.080 Uiso calc R 1 . .
C C9 0.3044(3) 0.24118(14) -0.01205(13) 0.0551(5) Uani d . 1 . .
C C10 0.2447(2) 0.57016(13) 0.03089(12) 0.0473(4) Uani d . 1 . .
C C11 0.2192(3) 0.66561(13) 0.01206(13) 0.0491(4) Uani d . 1 . .
C C12 0.2185(3) 0.73041(15) 0.08074(14) 0.0587(5) Uani d . 1 . .
H H12 0.2012 0.7927 0.0663 0.070 Uiso calc R 1 . .
C C13 0.2430(3) 0.70360(16) 0.16918(15) 0.0635(5) Uani d . 1 . .
H H13 0.2427 0.7472 0.2151 0.076 Uiso calc R 1 . .
C C14 0.2683(3) 0.61106(16) 0.18993(14) 0.0636(5) Uani d . 1 . .
H H14 0.2845 0.5924 0.2503 0.076 Uiso calc R 1 . .
C C15 0.2700(3) 0.54584(15) 0.12264(13) 0.0594(5) Uani d . 1 . .
H H15 0.2884 0.4840 0.1386 0.071 Uiso calc R 1 . .
C C16 0.2285(3) 0.40474(15) -0.20159(13) 0.0594(5) 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'
O O 0.0106 0.0060 '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'
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
C1 S1 C9 . . 92.84(9) ?
C10 N1 C1 . . 132.09(16) ?
C10 N1 H1 . . 114.0 ?
C1 N1 H1 . . 114.0 ?
O2 N2 O1 . . 121.38(19) ?
O2 N2 C11 . . 119.03(18) ?
O1 N2 C11 . . 119.59(17) ?
N1 C1 C2 . . 122.32(17) ?
N1 C1 S1 . . 128.18(14) ?
C2 C1 S1 . . 109.50(14) ?
C1 C2 C16 . . 120.52(18) ?
C1 C2 C3 . . 114.31(17) ?
C16 C2 C3 . . 125.17(18) ?
C9 C3 C2 . . 111.61(17) ?
C9 C3 C4 . . 126.28(19) ?
C2 C3 C4 . . 122.11(18) ?
C3 C4 C5 . . 115.66(17) ?
C3 C4 H4A . . 108.4 ?
C5 C4 H4A . . 108.4 ?
C3 C4 H4B . . 108.4 ?
C5 C4 H4B . . 108.4 ?
H4A C4 H4B . . 107.4 ?
C6 C5 C4 . . 115.93(19) ?
C6 C5 H5A . . 108.3 ?
C4 C5 H5A . . 108.3 ?
C6 C5 H5B . . 108.3 ?
C4 C5 H5B . . 108.3 ?
H5A C5 H5B . . 107.4 ?
C5 C6 C7 . . 115.73(19) ?
C5 C6 H6A . . 108.3 ?
C7 C6 H6A . . 108.3 ?
C5 C6 H6B . . 108.3 ?
C7 C6 H6B . . 108.3 ?
H6A C6 H6B . . 107.4 ?
C8 C7 C6 . . 115.5(2) ?
C8 C7 H7A . . 108.4 ?
C6 C7 H7A . . 108.4 ?
C8 C7 H7B . . 108.4 ?
C6 C7 H7B . . 108.4 ?
H7A C7 H7B . . 107.5 ?
C7 C8 C9 . . 115.43(19) ?
C7 C8 H8A . . 108.4 ?
C9 C8 H8A . . 108.4 ?
C7 C8 H8B . . 108.4 ?
C9 C8 H8B . . 108.4 ?
H8A C8 H8B . . 107.5 ?
C3 C9 C8 . . 129.69(19) ?
C3 C9 S1 . . 111.73(15) ?
C8 C9 S1 . . 118.46(15) ?
N1 C10 C15 . . 123.03(18) ?
N1 C10 C11 . . 121.17(16) ?
C15 C10 C11 . . 115.79(17) ?
C12 C11 C10 . . 121.68(18) ?
C12 C11 N2 . . 115.89(18) ?
C10 C11 N2 . . 122.43(16) ?
C13 C12 C11 . . 120.6(2) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C14 . . 119.26(19) ?
C12 C13 H13 . . 120.4 ?
C14 C13 H13 . . 120.4 ?
C15 C14 C13 . . 120.97(19) ?
C15 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C14 C15 C10 . . 121.7(2) ?
C14 C15 H15 . . 119.1 ?
C10 C15 H15 . . 119.1 ?
N3 C16 C2 . . 176.3(2) ?
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
S1 C1 . 1.7220(18) ?
S1 C9 . 1.735(2) ?
O1 N2 . 1.236(2) ?
O2 N2 . 1.215(2) ?
N1 C10 . 1.372(2) ?
N1 C1 . 1.379(2) ?
N1 H1 . 0.8600 ?
N2 C11 . 1.456(2) ?
N3 C16 . 1.139(3) ?
C1 C2 . 1.383(2) ?
C2 C16 . 1.419(3) ?
C2 C3 . 1.436(3) ?
C3 C9 . 1.357(3) ?
C3 C4 . 1.510(3) ?
C4 C5 . 1.531(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.513(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.520(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.506(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.508(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C10 C15 . 1.399(3) ?
C10 C11 . 1.415(3) ?
C11 C12 . 1.387(3) ?
C12 C13 . 1.361(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.377(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
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
N1 H1 O1 1_555 0.86 1.89 2.593(2) 138 yes
C12 H12 O2 1_555 0.93 2.33 2.657(3) 100 yes
C15 H15 S1 1_555 0.93 2.44 3.171(2) 135 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745068
