#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/96/2239638.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_2239638
loop_
_publ_author_name
'Gao, Ning'
'Luo, Hai-Kun'
'Qin, Rui-Rui'
'He, Ming-Yang'
_publ_section_title
;
 2,3,5,6-Tetrafluoro-1,4-bis({[(thiophen-2-yl)methylidene]amino}methyl)benzene
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o749
_journal_paper_doi               10.1107/S1600536814012434
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C18 H12 F4 N2 S2'
_chemical_formula_moiety         'C18 H12 F4 N2 S2'
_chemical_formula_sum            'C18 H12 F4 N2 S2'
_chemical_formula_weight         396.42
_chemical_name_systematic
;
2,3,5,6-Tetrafluoro-1,4-bis({[(thiophen-2-yl)methylidene]amino}methyl)benzene
;
_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                 95.371(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   15.500(7)
_cell_length_b                   4.865(2)
_cell_length_c                   11.713(6)
_cell_measurement_reflns_used    5195
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.71
_cell_measurement_theta_min      2.64
_cell_volume                     879.4(7)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6136
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9339
_exptl_absorpt_correction_T_min  0.9214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       shape
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0297
_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)+(0.0516P)²+0.2970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                1427
_reflns_number_total             1541
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2454sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        879.3(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239638
_cod_database_fobs_code          2239638
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
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_symmetry_multiplicity
C C1 0.43101(11) 0.7020(4) 0.85018(19) 0.0605(5) Uani d . 1 1
H H1 0.4750 0.8166 0.8818 0.073 Uiso calc R 1 1
C C2 0.40375(12) 0.6938(4) 0.73736(18) 0.0610(5) Uani d . 1 1
H H2 0.4266 0.8036 0.6826 0.073 Uiso calc R 1 1
C C3 0.33673(12) 0.5000(4) 0.71153(16) 0.0531(4) Uani d . 1 1
H H3 0.3110 0.4671 0.6378 0.064 Uiso calc R 1 1
C C4 0.31367(10) 0.3652(3) 0.80758(13) 0.0427(4) Uani d . 1 1
C C5 0.24772(9) 0.1542(3) 0.81301(13) 0.0428(4) Uani d . 1 1
H H5 0.2214 0.0838 0.7446 0.051 Uiso calc R 1 1
C C6 0.15903(10) -0.1584(3) 0.89660(15) 0.0464(4) Uani d . 1 1
H H6A 0.1831 -0.3231 0.9338 0.056 Uiso calc R 1 1
H H6B 0.1440 -0.2005 0.8162 0.056 Uiso calc R 1 1
C C7 0.07804(9) -0.0748(3) 0.95097(13) 0.0376(3) Uani d . 1 1
C C8 0.05197(9) -0.2024(3) 1.04813(12) 0.0388(3) Uani d . 1 1
C C9 0.02329(9) 0.1316(3) 0.90476(12) 0.0388(3) Uani d . 1 1
F F1 0.10088(7) -0.4083(2) 1.09813(8) 0.0566(3) Uani d . 1 1
F F2 0.04382(6) 0.2659(2) 0.80981(8) 0.0549(3) Uani d . 1 1
N N1 0.22433(8) 0.0614(3) 0.90663(12) 0.0445(3) Uani d . 1 1
S S1 0.37524(3) 0.47708(10) 0.92848(4) 0.05398(19) Uani 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'
F F 0.0171 0.0103 '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
C2 C1 S1 . . 112.19(15)
C2 C1 H1 . . 123.9
S1 C1 H1 . . 123.9
C1 C2 C3 . . 112.68(17)
C1 C2 H2 . . 123.7
C3 C2 H2 . . 123.7
C4 C3 C2 . . 112.58(17)
C4 C3 H3 . . 123.7
C2 C3 H3 . . 123.7
C3 C4 C5 . . 127.50(15)
C3 C4 S1 . . 110.81(13)
C5 C4 S1 . . 121.70(12)
N1 C5 C4 . . 123.20(14)
N1 C5 H5 . . 118.4
C4 C5 H5 . . 118.4
N1 C6 C7 . . 111.25(13)
N1 C6 H6A . . 109.4
C7 C6 H6A . . 109.4
N1 C6 H6B . . 109.4
C7 C6 H6B . . 109.4
H6A C6 H6B . . 108.0
C8 C7 C9 . . 115.32(13)
C8 C7 C6 . . 122.69(14)
C9 C7 C6 . . 121.97(14)
F1 C8 C9 . 3_557 118.11(13)
F1 C8 C7 . . 119.36(13)
C9 C8 C7 3_557 . 122.51(14)
F2 C9 C8 . 3_557 118.72(13)
F2 C9 C7 . . 119.11(13)
C8 C9 C7 3_557 . 122.16(14)
C5 N1 C6 . . 116.10(14)
C1 S1 C4 . . 91.74(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.350(3)
C1 S1 . 1.713(2)
C1 H1 . 0.9300
C2 C3 . 1.414(3)
C2 H2 . 0.9300
C3 C4 . 1.378(2)
C3 H3 . 0.9300
C4 C5 . 1.454(2)
C4 S1 . 1.7202(17)
C5 N1 . 1.270(2)
C5 H5 . 0.9300
C6 N1 . 1.469(2)
C6 C7 . 1.515(2)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 C8 . 1.389(2)
C7 C9 . 1.391(2)
C8 F1 . 1.3555(17)
C8 C9 3_557 1.380(2)
C9 F2 . 1.3531(18)
C9 C8 3_557 1.380(2)
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
C6 H6A F1 . 0.97 2.44 2.873(3) 107 no
C5 H5 F1 4_555 0.93 2.56 3.446(2) 159 yes
C6 H6B F1 4_555 0.97 2.63 3.542(2) 156 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_site_symmetry_4
_geom_torsion
S1 C1 C2 C3 . -0.6(2)
C1 C2 C3 C4 . 0.7(2)
C2 C3 C4 C5 . -179.95(15)
C2 C3 C4 S1 . -0.37(19)
C3 C4 C5 N1 . -172.30(16)
S1 C4 C5 N1 . 8.2(2)
N1 C6 C7 C8 . -113.68(16)
N1 C6 C7 C9 . 68.1(2)
C9 C7 C8 F1 . 179.22(13)
C6 C7 C8 F1 . 0.8(2)
C9 C7 C8 C9 3_557 0.5(2)
C6 C7 C8 C9 3_557 -177.86(14)
C8 C7 C9 F2 . -179.81(13)
C6 C7 C9 F2 . -1.4(2)
C8 C7 C9 C8 3_557 -0.5(2)
C6 C7 C9 C8 3_557 177.88(14)
C4 C5 N1 C6 . -177.93(14)
C7 C6 N1 C5 . -120.34(16)
C2 C1 S1 C4 . 0.36(15)
C3 C4 S1 C1 . 0.02(14)
C5 C4 S1 C1 . 179.62(14)
