#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/74/2227404.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227404
loop_
_publ_author_name
'Wang, Peng'
'Wan, Rong'
'Zhang, Jianqiang'
'Yu, Peng'
'He, Qiu'
_publ_section_title
;
 5-(2,3,4,5,6-Pentafluorophenyl)-1,3,4-thiadiazol-2-amine
;
_journal_coeditor_code           ER2081
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2765
_journal_paper_doi               10.1107/S1600536810039723
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C8 H2 F5 N3 S'
_chemical_formula_moiety         'C8 H2 F5 N3 S'
_chemical_formula_sum            'C8 H2 F5 N3 S'
_chemical_formula_weight         267.19
_chemical_melting_point_gt       523
_chemical_melting_point_lt       525
_chemical_name_systematic
;
5-(2,3,4,5,6-Pentafluorophenyl)-1,3,4-thiadiazol-2-amine
;
_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                 104.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.897(2)
_cell_length_b                   7.0680(14)
_cell_length_c                   11.553(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     939.8(3)
_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    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3428
_diffrn_reflns_theta_full        25.29
_diffrn_reflns_theta_max         25.29
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  0.9610
_exptl_absorpt_correction_T_min  0.8892
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.292
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0428
_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)+(0.0800P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                1283
_reflns_number_total             1709
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            er2081.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227404
_cod_database_fobs_code          2227404
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, 1/2-y, 1/2+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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.82940(7) 0.06662(10) 0.05893(6) 0.0461(3) Uani d . 1 . .
F F1 0.78775(15) -0.3360(2) -0.00245(14) 0.0569(5) Uani d . 1 . .
C C1 0.9155(2) 0.2602(4) 0.0479(2) 0.0404(6) Uani d . 1 . .
N N1 0.9659(2) 0.3683(4) 0.1416(2) 0.0524(6) Uani d . 1 . .
H H1A 1.0105 0.4601 0.1330 0.063 Uiso calc R 1 . .
H H1B 0.9537 0.3459 0.2106 0.063 Uiso calc R 1 . .
C C2 0.8165(2) 0.0294(4) -0.0925(2) 0.0389(6) Uani d . 1 . .
F F2 0.65099(17) -0.6042(2) -0.12921(18) 0.0685(6) Uani d . 1 . .
N N2 0.9298(2) 0.2855(4) -0.06011(19) 0.0472(6) Uani d . 1 . .
F F3 0.53266(17) -0.5342(3) -0.35867(18) 0.0747(6) Uani d . 1 . .
N N3 0.8725(2) 0.1519(3) -0.13946(19) 0.0451(6) Uani d . 1 . .
C C3 0.7437(2) -0.1198(4) -0.1630(2) 0.0387(6) Uani d . 1 . .
F F4 0.55308(16) -0.1942(3) -0.45890(14) 0.0689(6) Uani d . 1 . .
C C4 0.7312(2) -0.2972(4) -0.1154(2) 0.0429(6) Uani d . 1 . .
F F5 0.68393(17) 0.0780(2) -0.33282(15) 0.0609(5) Uani d . 1 . .
C C5 0.6609(3) -0.4358(4) -0.1800(3) 0.0489(7) Uani d . 1 . .
C C6 0.6009(2) -0.4016(4) -0.2954(3) 0.0502(7) Uani d . 1 . .
C C7 0.6116(2) -0.2282(4) -0.3459(2) 0.0482(7) Uani d . 1 . .
C C8 0.6812(2) -0.0900(4) -0.2800(2) 0.0453(7) 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'
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
C1 S C2 . . 87.05(12) ?
N2 C1 N1 . . 123.5(2) ?
N2 C1 S . . 113.5(2) ?
N1 C1 S . . 122.92(19) ?
C1 N1 H1A . . 120.0 ?
C1 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
N3 C2 C3 . . 122.8(2) ?
N3 C2 S . . 113.4(2) ?
C3 C2 S . . 123.72(19) ?
C1 N2 N3 . . 112.3(2) ?
C2 N3 N2 . . 113.8(2) ?
C8 C3 C4 . . 116.0(2) ?
C8 C3 C2 . . 121.8(2) ?
C4 C3 C2 . . 122.2(2) ?
F1 C4 C5 . . 118.0(3) ?
F1 C4 C3 . . 119.5(2) ?
C5 C4 C3 . . 122.4(3) ?
F2 C5 C6 . . 120.1(3) ?
F2 C5 C4 . . 120.0(3) ?
C6 C5 C4 . . 119.9(3) ?
F3 C6 C5 . . 120.5(3) ?
F3 C6 C7 . . 120.2(3) ?
C5 C6 C7 . . 119.3(2) ?
F4 C7 C6 . . 119.5(2) ?
F4 C7 C8 . . 120.3(3) ?
C6 C7 C8 . . 120.2(3) ?
F5 C8 C7 . . 117.2(2) ?
F5 C8 C3 . . 120.8(2) ?
C7 C8 C3 . . 122.1(3) ?
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
S C1 . 1.733(3) ?
S C2 . 1.737(3) ?
F1 C4 . 1.336(3) ?
C1 N2 . 1.313(3) ?
C1 N1 . 1.337(3) ?
N1 H1A . 0.8600 ?
N1 H1B . 0.8600 ?
C2 N3 . 1.292(3) ?
C2 C3 . 1.473(4) ?
F2 C5 . 1.345(3) ?
N2 N3 . 1.372(3) ?
F3 C6 . 1.331(3) ?
C3 C8 . 1.383(4) ?
C3 C4 . 1.392(4) ?
F4 C7 . 1.336(3) ?
C4 C5 . 1.379(4) ?
F5 C8 . 1.339(3) ?
C5 C6 . 1.365(5) ?
C6 C7 . 1.377(4) ?
C7 C8 . 1.379(4) ?
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 H1A N2 3_765 0.86 2.18 3.001(4) 160 yes
N1 H1B N3 4_555 0.86 2.19 3.013(3) 161 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 S C1 N2 . . . . -0.2(2) ?
C2 S C1 N1 . . . . -177.7(3) ?
C1 S C2 N3 . . . . 0.2(2) ?
C1 S C2 C3 . . . . -176.3(2) ?
N1 C1 N2 N3 . . . . 177.7(3) ?
S C1 N2 N3 . . . . 0.2(3) ?
C3 C2 N3 N2 . . . . 176.4(2) ?
S C2 N3 N2 . . . . -0.2(3) ?
C1 N2 N3 C2 . . . . 0.0(4) ?
N3 C2 C3 C8 . . . . -34.3(4) ?
S C2 C3 C8 . . . . 141.9(2) ?
N3 C2 C3 C4 . . . . 147.3(3) ?
S C2 C3 C4 . . . . -36.4(4) ?
C8 C3 C4 F1 . . . . -179.2(2) ?
C2 C3 C4 F1 . . . . -0.8(4) ?
C8 C3 C4 C5 . . . . 0.0(4) ?
C2 C3 C4 C5 . . . . 178.4(3) ?
F1 C4 C5 F2 . . . . -0.1(4) ?
C3 C4 C5 F2 . . . . -179.3(2) ?
F1 C4 C5 C6 . . . . 179.5(3) ?
C3 C4 C5 C6 . . . . 0.3(4) ?
F2 C5 C6 F3 . . . . -0.4(4) ?
C4 C5 C6 F3 . . . . -179.9(3) ?
F2 C5 C6 C7 . . . . 179.7(2) ?
C4 C5 C6 C7 . . . . 0.2(4) ?
F3 C6 C7 F4 . . . . 0.0(4) ?
C5 C6 C7 F4 . . . . 179.9(3) ?
F3 C6 C7 C8 . . . . 179.3(3) ?
C5 C6 C7 C8 . . . . -0.8(4) ?
F4 C7 C8 F5 . . . . 2.1(4) ?
C6 C7 C8 F5 . . . . -177.2(3) ?
F4 C7 C8 C3 . . . . -179.6(2) ?
C6 C7 C8 C3 . . . . 1.1(4) ?
C4 C3 C8 F5 . . . . 177.6(2) ?
C2 C3 C8 F5 . . . . -0.8(4) ?
C4 C3 C8 C7 . . . . -0.6(4) ?
C2 C3 C8 C7 . . . . -179.1(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26231149
