#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/33/2213395.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_2213395
loop_
_publ_author_name
'Anilkumar, G. N.'
'Kokila, M. K.'
Puttaraja
'Mohan, S.'
'Saravanan, J.'
_publ_section_title
N-(4-Fluorophenyl)-2-{[(1E)-(4-methoxyphenyl)methylene]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
_journal_coeditor_code           HK2216
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2077
_journal_page_last               o2079
_journal_paper_doi               10.1107/S1600536807012937
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C23 H21 F N2 O2 S'
_chemical_formula_moiety         'C23 H21 F N2 O2 S'
_chemical_formula_sum            'C23 H21 F N2 O2 S'
_chemical_formula_weight         408.48
_chemical_name_systematic
;
N-(4-Fluorophenyl)-2-{[(1E)-(4-methoxyphenyl)methylene]amino}-4,5,6,7-
tetrahydro-1-benzothiophene-3-carboxamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.874(3)
_cell_angle_beta                 81.656(2)
_cell_angle_gamma                70.473(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6363(11)
_cell_length_b                   11.0660(14)
_cell_length_c                   11.8153(15)
_cell_measurement_reflns_used    390
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      1.5
_cell_volume                     985.6(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material
'PARST (Nardelli, 1995) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9977
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS;, Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1206
_refine_ls_R_factor_gt           0.0704
_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)+(0.0916P)²+0.2792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1555
_refine_ls_wR_factor_ref         0.1821
_reflns_number_gt                2256
_reflns_number_total             3656
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2216.cif
_cod_data_source_block           I
_cod_database_code               2213395
_cod_database_fobs_code          2213395
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
F F1 -0.9235(3) 0.5757(3) 0.3689(2) 0.0947(8) Uani d . 1
N N1 -0.0098(3) 0.1310(3) 0.5498(2) 0.0462(7) Uani d . 1
N N2 -0.2507(3) 0.3389(3) 0.3921(3) 0.0553(8) Uani d . 1
H H2 -0.2183 0.2737 0.4602 0.066 Uiso calc R 1
O O1 -0.1608(4) 0.4575(3) 0.2099(3) 0.1073(13) Uani d . 1
O O2 -0.2932(3) -0.0964(3) 1.0927(2) 0.0750(8) Uani d . 1
S S1 0.29731(11) 0.07883(10) 0.44071(9) 0.0580(3) Uani d . 1
C C1 0.0491(4) 0.0301(4) 0.6463(3) 0.0525(9) Uani d . 1
H H1 0.1575 -0.0232 0.6426 0.063 Uiso calc R 1
C C2 0.0886(4) 0.1663(3) 0.4468(3) 0.0458(8) Uani d . 1
C C3 0.0400(4) 0.2737(3) 0.3384(3) 0.0465(8) Uani d . 1
C C4 0.1683(5) 0.3965(4) 0.1262(3) 0.0613(10) Uani d . 1
H H4A 0.1089 0.4856 0.1318 0.074 Uiso calc R 1
H H4B 0.1087 0.3807 0.0724 0.074 Uiso calc R 1
C C5 0.3372(6) 0.3971(5) 0.0723(4) 0.0927(15) Uani d . 1
H H5A 0.3274 0.4450 -0.0153 0.111 Uiso calc R 1
H H5B 0.3772 0.4493 0.1048 0.111 Uiso calc R 1
C C6 0.4594(6) 0.2645(5) 0.0936(4) 0.0950(16) Uani d . 1
H H6A 0.5641 0.2780 0.0597 0.114 Uiso calc R 1
H H6B 0.4288 0.2172 0.0501 0.114 Uiso calc R 1
C C7 0.4810(5) 0.1736(4) 0.2277(4) 0.0674(11) Uani d . 1
H H7A 0.5314 0.0787 0.2343 0.081 Uiso calc R 1
H H7B 0.5532 0.1985 0.2647 0.081 Uiso calc R 1
C C8 0.3182(4) 0.1893(4) 0.2943(3) 0.0525(9) Uani d . 1
C C9 0.1745(4) 0.2876(3) 0.2519(3) 0.0489(9) Uani d . 1
C C10 -0.1312(4) 0.3658(4) 0.3080(3) 0.0544(9) Uani d . 1
C C11 -0.4218(4) 0.4042(3) 0.3828(3) 0.0482(9) Uani d . 1
C C12 -0.5232(4) 0.3437(4) 0.4707(3) 0.0584(10) Uani d . 1
H H12 -0.4772 0.2624 0.5338 0.070 Uiso calc R 1
C C13 -0.6915(5) 0.4014(4) 0.4671(4) 0.0658(11) Uani d . 1
H H13 -0.7588 0.3604 0.5275 0.079 Uiso calc R 1
C C14 -0.7573(4) 0.5193(4) 0.3736(4) 0.0613(10) Uani d . 1
C C15 -0.6611(5) 0.5807(4) 0.2855(4) 0.0645(11) Uani d . 1
H H15 -0.7091 0.6612 0.2223 0.077 Uiso calc R 1
C C16 -0.4923(4) 0.5249(4) 0.2883(3) 0.0586(10) Uani d . 1
H H16 -0.4265 0.5676 0.2278 0.070 Uiso calc R 1
C C17 -0.0408(4) -0.0071(3) 0.7611(3) 0.0469(8) Uani d . 1
C C18 0.0367(5) -0.1140(4) 0.8624(3) 0.0628(10) Uani d . 1
H H18 0.1452 -0.1645 0.8542 0.075 Uiso calc R 1
C C19 -0.0409(5) -0.1478(4) 0.9743(3) 0.0601(10) Uani d . 1
H H19 0.0146 -0.2197 1.0410 0.072 Uiso calc R 1
C C20 -0.2023(4) -0.0740(4) 0.9871(3) 0.0534(9) Uani d . 1
C C21 -0.2830(5) 0.0313(4) 0.8863(3) 0.0640(11) Uani d . 1
H H21 -0.3925 0.0801 0.8940 0.077 Uiso calc R 1
C C22 -0.2039(4) 0.0642(4) 0.7761(3) 0.0561(10) Uani d . 1
H H22 -0.2599 0.1358 0.7096 0.067 Uiso calc R 1
C C23 -0.2185(6) -0.2059(5) 1.1990(4) 0.0870(14) Uani d . 1
H H23A -0.1806 -0.2901 1.1829 0.130 Uiso calc R 1
H H23B -0.2975 -0.2133 1.2654 0.130 Uiso calc R 1
H H23C -0.1272 -0.1883 1.2204 0.130 Uiso calc R 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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C1 N1 C2 120.9(3) ?
C10 N2 C11 128.4(3) yes
C10 N2 H2 115.8 ?
C11 N2 H2 115.8 ?
C20 O2 C23 118.2(3) ?
C8 S1 C2 91.67(17) ?
N1 C1 C17 124.7(3) ?
N1 C1 H1 117.6 ?
C17 C1 H1 117.6 ?
N1 C2 C3 126.3(3) yes
N1 C2 S1 122.8(2) ?
C3 C2 S1 110.9(3) ?
C2 C3 C9 112.4(3) ?
C2 C3 C10 125.9(3) yes
C9 C3 C10 121.7(3) ?
C9 C4 C5 112.2(3) ?
C9 C4 H4A 109.2 ?
C5 C4 H4A 109.2 ?
C9 C4 H4B 109.2 ?
C5 C4 H4B 109.2 ?
H4A C4 H4B 107.9 ?
C6 C5 C4 116.3(4) ?
C6 C5 H5A 108.2 ?
C4 C5 H5A 108.2 ?
C6 C5 H5B 108.2 ?
C4 C5 H5B 108.2 ?
H5A C5 H5B 107.4 ?
C5 C6 C7 114.2(4) ?
C5 C6 H6A 108.7 ?
C7 C6 H6A 108.7 ?
C5 C6 H6B 108.7 ?
C7 C6 H6B 108.7 ?
H6A C6 H6B 107.6 ?
C8 C7 C6 110.5(3) ?
C8 C7 H7A 109.6 ?
C6 C7 H7A 109.6 ?
C8 C7 H7B 109.6 ?
C6 C7 H7B 109.6 ?
H7A C7 H7B 108.1 ?
C9 C8 C7 126.4(3) ?
C9 C8 S1 112.3(3) ?
C7 C8 S1 121.3(3) ?
C8 C9 C3 112.6(3) ?
C8 C9 C4 120.3(3) ?
C3 C9 C4 127.1(3) ?
O1 C10 N2 122.1(3) ?
O1 C10 C3 120.6(3) ?
N2 C10 C3 117.3(3) ?
C12 C11 C16 118.7(3) ?
C12 C11 N2 118.2(3) ?
C16 C11 N2 123.1(3) ?
C11 C12 C13 121.3(3) ?
C11 C12 H12 119.3 ?
C13 C12 H12 119.3 ?
C14 C13 C12 118.8(4) ?
C14 C13 H13 120.6 ?
C12 C13 H13 120.6 ?
C15 C14 F1 119.7(4) ?
C15 C14 C13 121.3(3) ?
F1 C14 C13 118.9(4) ?
C14 C15 C16 120.6(4) ?
C14 C15 H15 119.7 ?
C16 C15 H15 119.7 ?
C11 C16 C15 119.2(4) ?
C11 C16 H16 120.4 ?
C15 C16 H16 120.4 ?
C18 C17 C22 117.3(3) yes
C18 C17 C1 120.3(3) ?
C22 C17 C1 122.4(3) ?
C19 C18 C17 122.3(3) ?
C19 C18 H18 118.9 ?
C17 C18 H18 118.9 ?
C18 C19 C20 119.2(3) ?
C18 C19 H19 120.4 ?
C20 C19 H19 120.4 ?
O2 C20 C19 125.2(3) ?
O2 C20 C21 115.5(3) ?
C19 C20 C21 119.3(3) yes
C22 C21 C20 120.7(4) ?
C22 C21 H21 119.7 ?
C20 C21 H21 119.7 ?
C21 C22 C17 121.2(3) ?
C21 C22 H22 119.4 ?
C17 C22 H22 119.4 ?
O2 C23 H23A 109.5 ?
O2 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
O2 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C14 1.360(4) ?
N1 C1 1.279(4) yes
N1 C2 1.386(4) ?
N2 C10 1.351(4) ?
N2 C11 1.411(4) yes
N2 H2 0.8600 ?
O1 C10 1.210(4) ?
O2 C20 1.359(4) ?
O2 C23 1.424(5) ?
S1 C8 1.727(4) yes
S1 C2 1.743(3) yes
C1 C17 1.449(5) ?
C1 H1 0.9300 ?
C2 C3 1.380(4) ?
C3 C9 1.440(5) ?
C3 C10 1.492(5) ?
C4 C9 1.514(5) ?
C4 C5 1.505(6) ?
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C6 1.447(6) ?
C5 H5A 0.9700 ?
C5 H5B 0.9700 ?
C6 C7 1.522(6) ?
C6 H6A 0.9700 ?
C6 H6B 0.9700 ?
C7 C8 1.498(5) ?
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 C9 1.357(5) yes
C11 C12 1.378(5) ?
C11 C16 1.389(5) ?
C12 C13 1.378(5) ?
C12 H12 0.9300 ?
C13 C14 1.359(5) ?
C13 H13 0.9300 ?
C14 C15 1.352(6) ?
C15 C16 1.380(5) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 C18 1.384(5) ?
C17 C22 1.388(5) ?
C18 C19 1.369(5) ?
C18 H18 0.9300 ?
C19 C20 1.380(5) ?
C19 H19 0.9300 ?
C20 C21 1.384(5) ?
C21 C22 1.358(5) ?
C21 H21 0.9300 ?
C22 H22 0.9300 ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 0.9600 ?
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 . 0.86 2.06 2.791(4) 142.00 yes
C1 H1 S1 . 0.93 2.54 3.010(4) 111.00 yes
C5 H5A O1 2_565 0.97 2.56 3.438(6) 150.00 yes
C16 H16 O1 . 0.93 2.23 2.817(5) 120.00 yes
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
_geom_torsion_publ_flag
C2 N1 C1 C17 174.6(3) yes
C1 N1 C2 C3 -179.0(3) ?
C1 N1 C2 S1 -0.5(4) ?
C8 S1 C2 N1 -177.4(3) ?
C8 S1 C2 C3 1.3(3) ?
N1 C2 C3 C9 176.5(3) ?
S1 C2 C3 C9 -2.1(4) ?
N1 C2 C3 C10 -5.1(5) ?
S1 C2 C3 C10 176.2(3) ?
C9 C4 C5 C6 39.2(6) yes
C4 C5 C6 C7 -54.6(6) yes
C5 C6 C7 C8 38.5(6) yes
C6 C7 C8 C9 -12.3(6) yes
C6 C7 C8 S1 168.7(3) ?
C2 S1 C8 C9 0.0(3) ?
C2 S1 C8 C7 179.1(3) ?
C7 C8 C9 C3 179.8(3) ?
S1 C8 C9 C3 -1.2(4) ?
C7 C8 C9 C4 -0.6(6) yes
S1 C8 C9 C4 178.5(3) ?
C2 C3 C9 C8 2.1(4) ?
C10 C3 C9 C8 -176.3(3) ?
C2 C3 C9 C4 -177.5(3) ?
C10 C3 C9 C4 4.1(5) ?
C5 C4 C9 C8 -11.6(5) yes
C5 C4 C9 C3 168.0(4) ?
C11 N2 C10 O1 2.0(6) ?
C11 N2 C10 C3 -175.6(3) yes
C2 C3 C10 O1 179.8(4) ?
C9 C3 C10 O1 -2.0(6) ?
C2 C3 C10 N2 -2.5(5) ?
C9 C3 C10 N2 175.7(3) ?
C10 N2 C11 C12 168.1(4) ?
C10 N2 C11 C16 -10.9(6) ?
C16 C11 C12 C13 -0.7(6) ?
N2 C11 C12 C13 -179.7(3) ?
C11 C12 C13 C14 0.8(6) ?
C12 C13 C14 C15 -0.4(6) ?
C12 C13 C14 F1 179.2(3) ?
F1 C14 C15 C16 -179.8(3) ?
C13 C14 C15 C16 -0.2(6) ?
C12 C11 C16 C15 0.1(5) ?
N2 C11 C16 C15 179.1(3) ?
C14 C15 C16 C11 0.3(6) ?
N1 C1 C17 C18 -176.6(3) ?
N1 C1 C17 C22 1.0(6) ?
C22 C17 C18 C19 -1.3(6) ?
C1 C17 C18 C19 176.3(4) ?
C17 C18 C19 C20 0.5(6) ?
C23 O2 C20 C19 -1.2(6) ?
C23 O2 C20 C21 178.3(4) ?
C18 C19 C20 O2 -179.7(4) ?
C18 C19 C20 C21 0.9(6) ?
O2 C20 C21 C22 179.2(4) ?
C19 C20 C21 C22 -1.4(6) ?
C20 C21 C22 C17 0.5(6) ?
C18 C17 C22 C21 0.8(6) ?
C1 C17 C22 C21 -176.8(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655227
