#------------------------------------------------------------------------------
#$Date: 2020-06-06 08:29:11 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252980 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243423.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_2243423
loop_
_publ_author_name
'Askerov, Rizvan K.'
'Maharramov, Abel M.'
'Khalilov, Ali N.'
'Akkurt, Mehmet'
'Akobirshoeva, Anzurat A.'
'Osmanov, V. K.'
'Borisov, A. V.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 1-(2-fluorophenyl)-1H-tetrazole-5(4H)-thione
;
_journal_coeditor_code           YK2131
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1007
_journal_page_last               1011
_journal_paper_doi               10.1107/S2056989020007033
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C7 H5 F N4 S'
_chemical_formula_moiety         'C7 H5 F N4 S'
_chemical_formula_sum            'C7 H5 F N4 S'
_chemical_formula_weight         196.21
_chemical_name_systematic
;
1-(2-Fluorophenyl)-1H-tetrazole-5(4H)-thione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.0090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.5593(11)
_cell_length_b                   9.2849(5)
_cell_length_c                   7.7927(4)
_cell_measurement_reflns_used    4417
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.37
_cell_volume                     1653.92(15)
_computing_cell_refinement
;
SAINT (Bruker, 2003)
;
_computing_data_collection
;
APEX2 (Bruker, 2003)
;
_computing_data_reduction
;
SAINT (Bruker, 2003)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014/5 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9005
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.469
_diffrn_reflns_theta_min         1.782
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.223
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0487P)²+1.1614P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                2135
_reflns_number_total             2406
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2131sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243423
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.922
_shelx_estimated_absorpt_t_max   0.971
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.51038(2) 0.75776(4) 0.51736(5) 0.03900(12) Uani d 1 . .
F F1 0.71634(4) 0.73413(10) 0.64199(14) 0.0536(3) Uani d 1 . .
N N1 0.61196(5) 0.77955(12) 0.40738(16) 0.0346(2) Uani d 1 . .
N N2 0.64339(6) 0.88176(13) 0.3424(2) 0.0480(3) Uani d 1 . .
N N3 0.61568(6) 1.00050(13) 0.3346(2) 0.0494(3) Uani d 1 . .
N N4 0.56649(5) 0.97577(12) 0.39123(17) 0.0399(3) Uani d 1 . .
H H4 0.5428(9) 1.048(2) 0.408(3) 0.060(5) Uiso d 1 . .
C C5 0.56255(5) 0.83768(13) 0.43970(17) 0.0320(2) Uani d 1 . .
C C6 0.63424(5) 0.63719(13) 0.44289(17) 0.0314(2) Uani d 1 . .
C C7 0.68772(6) 0.61740(14) 0.56178(18) 0.0361(3) Uani d 1 . .
C C8 0.71115(6) 0.48238(16) 0.6014(2) 0.0434(3) Uani d 1 . .
H H8A 0.747433 0.470495 0.680048 0.052 Uiso calc 1 . .
C C9 0.67955(7) 0.36465(16) 0.5217(2) 0.0444(3) Uani d 1 . .
H H9A 0.694563 0.272435 0.547932 0.053 Uiso calc 1 . .
C C10 0.62584(7) 0.38250(15) 0.4034(2) 0.0419(3) Uani d 1 . .
H H10A 0.604979 0.302279 0.351172 0.050 Uiso calc 1 . .
C C11 0.60297(6) 0.51874(14) 0.36219(19) 0.0369(3) Uani d 1 . .
H H11A 0.567110 0.530830 0.281472 0.044 Uiso calc 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
_geom_angle_publ_flag
C5 N1 N2 . . 110.84(11) ?
C5 N1 C6 . . 128.58(11) ?
N2 N1 C6 . . 120.44(10) ?
N3 N2 N1 . . 107.44(11) ?
N2 N3 N4 . . 107.81(11) ?
C5 N4 N3 . . 112.04(11) ?
C5 N4 H4 . . 125.3(13) ?
N3 N4 H4 . . 122.1(13) ?
N4 C5 N1 . . 101.86(11) ?
N4 C5 S1 . . 129.19(10) ?
N1 C5 S1 . . 128.94(10) ?
C7 C6 C11 . . 119.73(12) ?
C7 C6 N1 . . 119.10(11) ?
C11 C6 N1 . . 121.17(11) ?
F1 C7 C8 . . 120.05(12) ?
F1 C7 C6 . . 118.43(12) ?
C8 C7 C6 . . 121.51(12) ?
C7 C8 C9 . . 118.49(13) ?
C7 C8 H8A . . 120.8 ?
C9 C8 H8A . . 120.8 ?
C8 C9 C10 . . 120.72(13) ?
C8 C9 H9A . . 119.6 ?
C10 C9 H9A . . 119.6 ?
C11 C10 C9 . . 120.44(13) ?
C11 C10 H10A . . 119.8 ?
C9 C10 H10A . . 119.8 ?
C10 C11 C6 . . 119.10(13) ?
C10 C11 H11A . . 120.4 ?
C6 C11 H11A . . 120.4 ?
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 C5 . 1.6696(13) ?
F1 C7 . 1.3476(15) ?
N1 C5 . 1.3608(15) ?
N1 N2 . 1.3735(16) ?
N1 C6 . 1.4244(16) ?
N2 N3 . 1.2752(16) ?
N3 N4 . 1.3558(17) ?
N4 C5 . 1.3462(17) ?
N4 H4 . 0.90(2) ?
C6 C7 . 1.3836(18) ?
C6 C11 . 1.3868(18) ?
C7 C8 . 1.3745(19) ?
C8 C9 . 1.382(2) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.384(2) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.3818(19) ?
C10 H10A . 0.9300 ?
C11 H11A . 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
N4 H4 S1 5_676 0.90(2) 2.35(2) 3.2456(12) 173.2(18) yes
C5 S1 Cg1 2_655 1.6696(13) 3.7678(7) 4.0760(14) 88.31(5) no
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 N3 . . . . 0.45(18) ?
C6 N1 N2 N3 . . . . -175.58(13) ?
N1 N2 N3 N4 . . . . -0.81(18) ?
N2 N3 N4 C5 . . . . 0.94(19) ?
N3 N4 C5 N1 . . . . -0.62(16) ?
N3 N4 C5 S1 . . . . 179.93(11) ?
N2 N1 C5 N4 . . . . 0.11(15) ?
C6 N1 C5 N4 . . . . 175.73(13) ?
N2 N1 C5 S1 . . . . 179.57(11) ?
C6 N1 C5 S1 . . . . -4.8(2) ?
C5 N1 C6 C7 . . . . -116.67(15) ?
N2 N1 C6 C7 . . . . 58.59(18) ?
C5 N1 C6 C11 . . . . 62.53(19) ?
N2 N1 C6 C11 . . . . -122.21(15) ?
C11 C6 C7 F1 . . . . -178.12(12) ?
N1 C6 C7 F1 . . . . 1.09(18) ?
C11 C6 C7 C8 . . . . 0.5(2) ?
N1 C6 C7 C8 . . . . 179.75(13) ?
F1 C7 C8 C9 . . . . 177.56(13) ?
C6 C7 C8 C9 . . . . -1.1(2) ?
C7 C8 C9 C10 . . . . 0.7(2) ?
C8 C9 C10 C11 . . . . 0.3(2) ?
C9 C10 C11 C6 . . . . -0.9(2) ?
C7 C6 C11 C10 . . . . 0.4(2) ?
N1 C6 C11 C10 . . . . -178.76(12) ?

_cod_database_fobs_code 2243423
