#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/38/2213860.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_2213860
loop_
_publ_author_name
'Kaynak, F. Betül '
_publ_section_title
2-[2-(p-Chlorophenyl)benzimidazol-1-ylmethyl]-5-(2-fluoroanilino)-1,3,4-thiadiazole
_journal_coeditor_code           KJ2045
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2798
_journal_page_last               o2799
_journal_paper_doi               10.1107/S1600536807021265
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C22 H15 Cl1 F1 N5 S1'
_chemical_formula_moiety         'C22 H15 Cl1 F1 N5 S1'
_chemical_formula_sum            'C22 H15 Cl F N5 S'
_chemical_formula_weight         435.9
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 127.599(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.583(5)
_cell_length_b                   9.9377(14)
_cell_length_c                   20.207(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.08
_cell_measurement_theta_min      9.92
_cell_volume                     4070.3(13)
_computing_cell_refinement       'CAD-4 Express (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 Express (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4033
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.9274
_exptl_absorpt_correction_T_min  0.8939
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.285
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+1.4370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                2473
_reflns_number_total             3948
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2045.cif
_cod_data_source_block           I
_cod_original_cell_volume        4070.3(12)
_cod_database_code               2213860
_cod_database_fobs_code          2213860
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
C C2 0.73303(12) 0.1194(2) 0.74358(15) 0.0387(6) Uani d . 1
C C4 0.60582(14) 0.1607(3) 0.76226(19) 0.0565(8) Uani d . 1
H H4 0.5652 0.1785 0.7114 0.068 Uiso calc R 1
C C5 0.61246(16) 0.1521(3) 0.8349(2) 0.0648(9) Uani d . 1
H H5A 0.5755 0.1632 0.8329 0.078 Uiso calc R 1
C C6 0.67349(17) 0.1272(3) 0.9115(2) 0.0650(9) Uani d . 1
H H6 0.6761 0.1226 0.9594 0.078 Uiso calc R 1
C C7 0.72965(15) 0.1093(3) 0.91821(17) 0.0542(7) Uani d . 1
H H7 0.7704 0.0944 0.9695 0.065 Uiso calc R 1
C C8 0.72274(12) 0.1146(2) 0.84460(16) 0.0406(6) Uani d . 1
C C9 0.66244(12) 0.1418(3) 0.76784(15) 0.0421(6) Uani d . 1
C C10 0.76349(12) 0.1167(2) 0.70061(15) 0.0393(6) Uani d . 1
C C11 0.79438(13) 0.0027(3) 0.69954(16) 0.0472(7) Uani d . 1
H H11 0.7964 -0.0749 0.7268 0.057 Uiso calc R 1
C C12 0.82210(13) 0.0034(3) 0.65850(17) 0.0531(7) Uani d . 1
H H12 0.8417 -0.0737 0.6566 0.064 Uiso calc R 1
C C13 0.82016(13) 0.1196(3) 0.62069(16) 0.0503(7) Uani d . 1
C C14 0.78944(15) 0.2329(3) 0.61965(18) 0.0614(8) Uani d . 1
H H14 0.7879 0.3102 0.5926 0.074 Uiso calc R 1
C C15 0.76056(14) 0.2310(3) 0.65947(17) 0.0534(7) Uani d . 1
H H15 0.739 0.3072 0.6585 0.064 Uiso calc R 1
C C16 0.83863(12) 0.0835(3) 0.89070(15) 0.0415(6) Uani d . 1
H H16A 0.8571 0.0466 0.8646 0.050 Uiso calc R 1
H H16B 0.8474 0.0203 0.933 0.050 Uiso calc R 1
C C17 0.87199(11) 0.2149(2) 0.93180(14) 0.0363(6) Uani d . 1
C C18 0.91232(11) 0.4387(3) 0.97000(14) 0.0357(6) Uani d . 1
C C19 0.96178(12) 0.6568(3) 1.03957(15) 0.0396(6) Uani d . 1
C C20 0.99454(13) 0.6191(3) 1.12250(16) 0.0523(7) Uani d . 1
H H20 0.9934 0.5301 1.1357 0.063 Uiso calc R 1
C C21 1.02871(15) 0.7142(4) 1.18505(18) 0.0630(9) Uani d . 1
H H21 1.0507 0.6881 1.2403 0.076 Uiso calc R 1
C C22 1.03085(15) 0.8469(4) 1.1672(2) 0.0662(9) Uani d . 1
H H22 1.0537 0.9098 1.2101 0.079 Uiso calc R 1
C C23 0.99901(14) 0.8862(3) 1.08553(19) 0.0572(8) Uani d . 1
H H23 0.9999 0.9754 1.0723 0.069 Uiso calc R 1
C C24 0.96614(12) 0.7904(3) 1.02453(16) 0.0452(7) Uani d . 1
Cl Cl1 0.86142(4) 0.12627(11) 0.57715(5) 0.0822(3) Uani d . 1
F F1 0.93480(8) 0.82834(16) 0.94364(10) 0.0615(5) Uani d . 1
N N1 0.76745(10) 0.0981(2) 0.82778(12) 0.0382(5) Uani d . 1
N N2 0.67032(10) 0.1453(2) 0.70541(12) 0.0440(5) Uani d . 1
N N3 0.91089(11) 0.2316(2) 1.01154(13) 0.0468(6) Uani d . 1
N N4 0.93564(11) 0.3616(2) 1.03505(12) 0.0463(6) Uani d . 1
N N5 0.92497(10) 0.5713(2) 0.97037(13) 0.0417(5) Uani d . 1
S S1 0.86067(3) 0.35519(7) 0.87464(4) 0.0449(2) Uani d . 1
H H5 0.9030(12) 0.609(2) 0.9211(15) 0.043(7) Uiso 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-11 -3 4
-2 2 8
-9 3 2
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
N2 C2 N1 112.8(2) no
N2 C2 C10 123.4(2) ?
N1 C2 C10 123.7(2) ?
C5 C4 C9 117.4(3) ?
C4 C5 C6 121.5(3) ?
C7 C6 C5 122.0(3) ?
C6 C7 C8 116.7(3) ?
N1 C8 C7 132.3(2) ?
N1 C8 C9 105.6(2) no
C7 C8 C9 122.1(3) ?
C8 C9 N2 109.8(2) no
C8 C9 C4 120.4(2) ?
N2 C9 C4 129.8(3) ?
C15 C10 C11 118.9(2) ?
C15 C10 C2 118.9(2) ?
C11 C10 C2 122.2(2) ?
C12 C11 C10 120.7(3) ?
C13 C12 C11 118.8(3) ?
C14 C13 C12 121.9(3) ?
C14 C13 Cl1 118.8(2) ?
C12 C13 Cl1 119.2(2) ?
C13 C14 C15 119.0(3) ?
C10 C15 C14 120.6(3) ?
N1 C16 C17 112.4(2) no
N3 C17 C16 123.3(2) ?
N3 C17 S1 114.88(19) ?
C16 C17 S1 121.84(17) ?
N4 C18 N5 127.0(2) ?
N4 C18 S1 113.89(19) ?
N5 C18 S1 119.08(18) ?
C24 C19 C20 117.0(2) ?
C24 C19 N5 117.3(2) ?
C20 C19 N5 125.7(3) ?
C21 C20 C19 119.8(3) ?
C22 C21 C20 121.3(3) ?
C23 C22 C21 119.8(3) ?
C24 C23 C22 118.1(3) ?
F1 C24 C23 118.4(3) ?
F1 C24 C19 117.6(2) ?
C23 C24 C19 124.0(3) ?
C2 N1 C8 106.5(2) no
C2 N1 C16 127.7(2) ?
C8 N1 C16 125.1(2) ?
C2 N2 C9 105.2(2) no
C17 N3 N4 113.0(2) ?
C18 N4 N3 111.56(19) no
C18 N5 C19 127.5(2) no
C17 S1 C18 86.57(12) no
C5 C4 H4 121.3 ?
C9 C4 H4 121.3 ?
C4 C5 H5A 119.3 ?
C6 C5 H5A 119.3 ?
C7 C6 H6 119.1 ?
C5 C6 H6 119.1 ?
C6 C7 H7 121.6 ?
C8 C7 H7 121.6 ?
C12 C11 H11 119.6 ?
C10 C11 H11 119.6 ?
C13 C12 H12 120.6 ?
C11 C12 H12 120.6 ?
C13 C14 H14 120.5 ?
C15 C14 H14 120.5 ?
C10 C15 H15 119.7 ?
C14 C15 H15 119.7 ?
N1 C16 H16A 109.1 ?
C17 C16 H16A 109.1 ?
N1 C16 H16B 109.1 ?
C17 C16 H16B 109.1 ?
H16A C16 H16B 107.9 ?
C21 C20 H20 120.1 ?
C19 C20 H20 120.1 ?
C22 C21 H21 119.3 ?
C20 C21 H21 119.3 ?
C21 C22 H22 120.1 ?
C23 C22 H22 120.1 ?
C24 C23 H23 121.0 ?
C22 C23 H23 121.0 ?
C18 N5 H5 115.7(16) ?
C19 N5 H5 116.3(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C2 N2 1.313(3) yes
C2 N1 1.374(3) yes
C2 C10 1.479(4) ?
C4 C5 1.373(4) ?
C4 C9 1.395(4) ?
C5 C6 1.395(4) ?
C6 C7 1.370(4) ?
C7 C8 1.387(4) ?
C8 N1 1.388(3) yes
C8 C9 1.393(3) yes
C9 N2 1.394(3) yes
C10 C15 1.382(4) ?
C10 C11 1.389(3) ?
C11 C12 1.381(4) ?
C12 C13 1.369(4) ?
C13 C14 1.366(4) ?
C13 Cl1 1.740(3) ?
C14 C15 1.385(4) ?
C16 N1 1.459(3) ?
C16 C17 1.503(3) ?
C17 N3 1.288(3) yes
C17 S1 1.719(2) yes
C18 N4 1.309(3) yes
C18 N5 1.356(3) ?
C18 S1 1.744(2) yes
C19 C24 1.381(4) ?
C19 C20 1.392(3) ?
C19 N5 1.399(3) ?
C20 C21 1.381(4) ?
C21 C22 1.378(4) ?
C22 C23 1.378(4) ?
C23 C24 1.367(4) ?
C24 F1 1.363(3) ?
N3 N4 1.389(3) yes
N5 H5 0.87(2) ?
C4 H4 0.9300 ?
C5 H5A 0.9300 ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C11 H11 0.9300 ?
C12 H12 0.9300 ?
C14 H14 0.9300 ?
C15 H15 0.9300 ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C20 H20 0.9300 ?
C21 H21 0.9300 ?
C22 H22 0.9300 ?
C23 H23 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
N5 H5 F1 . 0.87(2) 2.27(2) 2.654(3) 106.3(18)
C20 H20 N4 . 0.93 2.340 2.948(4) 123
N5 H5 N2 4_656 0.87(2) 2.08(2) 2.921(3) 161.3
C6 H6 Cg(1) 7_556 0.93 3.1418 3.940(5) 145.05
C11 H11 Cg(2) 4_555 0.93 2.9984 3.806(3) 146.17
C12 H12 Cg(3) 4_555 0.93 2.9162 3.676(3) 139.82
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
C9 C4 C5 C6 0.7(5)
C4 C5 C6 C7 -0.3(5)
C5 C6 C7 C8 -1.3(5)
C6 C7 C8 N1 -178.3(3)
C6 C7 C8 C9 2.6(4)
C7 C8 C9 N2 178.0(2)
N1 C8 C9 N2 -1.4(3)
C7 C8 C9 C4 -2.2(4)
N1 C8 C9 C4 178.4(2)
C5 C4 C9 C8 0.5(4)
C5 C4 C9 N2 -179.8(3)
N2 C2 C10 C15 58.7(3)
N1 C2 C10 C15 -119.9(3)
N2 C2 C10 C11 -120.6(3)
N1 C2 C10 C11 60.9(3)
C15 C10 C11 C12 0.4(4)
C2 C10 C11 C12 179.7(2)
C10 C11 C12 C13 1.7(4)
C11 C12 C13 C14 -2.6(4)
C11 C12 C13 Cl1 174.1(2)
C12 C13 C14 C15 1.3(4)
Cl1 C13 C14 C15 -175.4(2)
C11 C10 C15 C14 -1.7(4)
C2 C10 C15 C14 179.0(3)
C13 C14 C15 C10 0.9(4)
N1 C16 C17 N3 127.3(2)
N1 C16 C17 S1 -52.7(3)
C24 C19 C20 C21 0.6(4)
N5 C19 C20 C21 -179.3(2)
C19 C20 C21 C22 0.5(5)
C20 C21 C22 C23 -0.8(5)
C21 C22 C23 C24 -0.1(5)
C22 C23 C24 F1 -179.7(2)
C22 C23 C24 C19 1.3(4)
C20 C19 C24 F1 179.4(2)
N5 C19 C24 F1 -0.6(3)
C20 C19 C24 C23 -1.6(4)
N5 C19 C24 C23 178.4(2)
N2 C2 N1 C8 -1.2(3)
C10 C2 N1 C8 177.5(2)
N2 C2 N1 C16 -171.8(2)
C10 C2 N1 C16 6.9(4)
C7 C8 N1 C2 -177.7(3)
C9 C8 N1 C2 1.5(3)
C7 C8 N1 C16 -6.8(4)
C9 C8 N1 C16 172.4(2)
C17 C16 N1 C2 92.9(3)
C17 C16 N1 C8 -76.1(3)
N1 C2 N2 C9 0.4(3)
C10 C2 N2 C9 -178.3(2)
C8 C9 N2 C2 0.6(3)
C4 C9 N2 C2 -179.1(3)
C16 C17 N3 N4 -179.7(2)
S1 C17 N3 N4 0.3(3)
N5 C18 N4 N3 178.3(2)
S1 C18 N4 N3 -2.5(3)
C17 N3 N4 C18 1.4(3)
N4 C18 N5 C19 -4.7(4)
S1 C18 N5 C19 176.1(2)
C24 C19 N5 C18 -177.7(2)
C20 C19 N5 C18 2.2(4)
N3 C17 S1 C18 -1.4(2)
C16 C17 S1 C18 178.6(2)
N4 C18 S1 C17 2.21(19)
N5 C18 S1 C17 -178.6(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4981235
