#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/18/2221888.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_2221888
loop_
_publ_author_name
'Wang, Yao'
'Wan, Rong'
'Han, Feng'
'Wang, Peng'
_publ_section_title
;
 5-(2-Fluoro-4-nitrophenyl)-1,3,4-thiadiazole-2-amine
;
_journal_coeditor_code           AT2775
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1250
_journal_paper_doi               10.1107/S1600536809016614
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H5 F N4 O2 S'
_chemical_formula_moiety         'C8 H5 F N4 O2 S'
_chemical_formula_sum            'C8 H5 F N4 O2 S'
_chemical_formula_weight         240.22
_chemical_melting_point          476
_chemical_name_systematic
;
5-(2-Fluoro-4-nitrophenyl)-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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.55(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1780(18)
_cell_length_b                   9.3720(19)
_cell_length_c                   11.413(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     958.2(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1832
_diffrn_reflns_theta_full        25.23
_diffrn_reflns_theta_max         25.23
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_correction_T_min  0.9345
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.467
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1720
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0557
_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)+(0.1000P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1944
_reflns_number_gt                1301
_reflns_number_total             1720
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2775.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2221888
_cod_database_fobs_code          2221888
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_disorder_assembly
_atom_site_disorder_group
S S 0.65883(14) 0.15613(12) 0.66472(10) 0.0442(4) Uani d . 1 . .
F F 0.6863(3) -0.1515(3) 0.6466(2) 0.0539(8) Uani d . 1 . .
N N1 0.9259(5) -0.4021(5) 0.3718(4) 0.0537(11) Uani d . 1 . .
C C1 0.8706(5) -0.2697(4) 0.4162(4) 0.0404(10) Uani d . 1 . .
O O1 1.0171(6) -0.3935(5) 0.3093(4) 0.0892(15) Uani d . 1 . .
O O2 0.8765(4) -0.5153(4) 0.4009(4) 0.0656(11) Uani d . 1 . .
N N2 0.6452(5) 0.2128(4) 0.4420(3) 0.0449(9) Uani d . 1 . .
C C2 0.8888(5) -0.1427(5) 0.3565(4) 0.0448(11) Uani d . 1 . .
H H2B 0.9387 -0.1415 0.2938 0.054 Uiso calc R 1 . .
N N3 0.5854(5) 0.3311(4) 0.4867(3) 0.0475(10) Uani d . 1 . .
C C3 0.8298(5) -0.0180(5) 0.3938(4) 0.0412(10) Uani d . 1 . .
H H3B 0.8386 0.0674 0.3544 0.049 Uiso calc R 1 . .
N N4 0.5320(5) 0.4162(4) 0.6663(3) 0.0535(11) Uani d . 1 . .
H H4A 0.4951 0.4943 0.6329 0.064 Uiso calc R 1 . .
H H4B 0.5347 0.4016 0.7412 0.064 Uiso calc R 1 . .
C C4 0.7568(5) -0.0197(4) 0.4903(4) 0.0358(10) Uani d . 1 . .
C C5 0.7505(5) -0.1484(5) 0.5495(4) 0.0388(10) Uani d . 1 . .
C C6 0.8026(5) -0.2754(5) 0.5131(4) 0.0421(10) Uani d . 1 . .
H H6A 0.7925 -0.3609 0.5519 0.050 Uiso calc R 1 . .
C C7 0.6885(5) 0.1134(4) 0.5224(4) 0.0367(10) Uani d . 1 . .
C C8 0.5851(5) 0.3175(4) 0.6019(4) 0.0378(10) Uani d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S 0.0663(8) 0.0343(6) 0.0343(6) 0.0124(5) 0.0166(5) 0.0053(4)
F 0.0753(19) 0.0440(16) 0.0517(16) 0.0078(13) 0.0340(14) 0.0074(12)
N1 0.069(3) 0.038(2) 0.054(2) 0.013(2) 0.012(2) -0.0076(19)
C1 0.047(2) 0.031(2) 0.042(2) 0.0064(19) 0.0066(19) -0.0057(19)
O1 0.125(4) 0.067(3) 0.096(3) 0.032(3) 0.068(3) -0.003(2)
O2 0.075(3) 0.041(2) 0.075(3) 0.0038(18) 0.003(2) -0.0161(19)
N2 0.068(3) 0.0328(19) 0.0379(19) 0.0120(18) 0.0200(18) 0.0030(16)
C2 0.053(3) 0.040(3) 0.045(2) 0.006(2) 0.019(2) -0.005(2)
N3 0.073(3) 0.0292(19) 0.045(2) 0.0150(18) 0.0237(19) 0.0044(16)
C3 0.055(3) 0.032(2) 0.038(2) 0.0018(19) 0.014(2) 0.0020(18)
N4 0.084(3) 0.040(2) 0.039(2) 0.020(2) 0.018(2) 0.0030(17)
C4 0.040(2) 0.032(2) 0.034(2) 0.0034(18) 0.0068(18) -0.0020(17)
C5 0.043(2) 0.037(2) 0.038(2) 0.0015(19) 0.0131(18) -0.0014(18)
C6 0.056(3) 0.030(2) 0.041(2) 0.003(2) 0.012(2) 0.0016(18)
C7 0.042(2) 0.031(2) 0.038(2) 0.0026(18) 0.0120(19) 0.0016(18)
C8 0.048(2) 0.032(2) 0.035(2) 0.0058(18) 0.0101(19) 0.0053(17)
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'
O O 0.0106 0.0060 '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
C8 S C7 . . 86.65(19) ?
O1 N1 O2 . . 124.0(4) ?
O1 N1 C1 . . 118.6(4) ?
O2 N1 C1 . . 117.4(4) ?
C6 C1 C2 . . 123.0(4) ?
C6 C1 N1 . . 119.4(4) ?
C2 C1 N1 . . 117.6(4) ?
C7 N2 N3 . . 113.4(3) ?
C3 C2 C1 . . 118.0(4) ?
C3 C2 H2B . . 121.0 ?
C1 C2 H2B . . 121.0 ?
C8 N3 N2 . . 112.1(3) ?
C2 C3 C4 . . 120.8(4) ?
C2 C3 H3B . . 119.6 ?
C4 C3 H3B . . 119.6 ?
C8 N4 H4A . . 120.0 ?
C8 N4 H4B . . 120.0 ?
H4A N4 H4B . . 120.0 ?
C5 C4 C3 . . 117.9(4) ?
C5 C4 C7 . . 123.2(4) ?
C3 C4 C7 . . 118.9(4) ?
F C5 C6 . . 117.7(4) ?
F C5 C4 . . 119.0(4) ?
C6 C5 C4 . . 123.3(4) ?
C5 C6 C1 . . 116.9(4) ?
C5 C6 H6A . . 121.5 ?
C1 C6 H6A . . 121.5 ?
N2 C7 C4 . . 120.6(4) ?
N2 C7 S . . 113.8(3) ?
C4 C7 S . . 125.7(3) ?
N3 C8 N4 . . 124.0(4) ?
N3 C8 S . . 114.1(3) ?
N4 C8 S . . 121.9(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 C8 . 1.746(4) ?
S C7 . 1.750(4) ?
F C5 . 1.363(5) ?
N1 O1 . 1.214(6) ?
N1 O2 . 1.227(5) ?
N1 C1 . 1.472(6) ?
C1 C6 . 1.384(6) ?
C1 C2 . 1.400(6) ?
N2 C7 . 1.308(5) ?
N2 N3 . 1.382(5) ?
C2 C3 . 1.392(6) ?
C2 H2B . 0.9300 ?
N3 C8 . 1.321(6) ?
C3 C4 . 1.409(6) ?
C3 H3B . 0.9300 ?
N4 C8 . 1.338(6) ?
N4 H4A . 0.8600 ?
N4 H4B . 0.8600 ?
C4 C5 . 1.389(6) ?
C4 C7 . 1.478(6) ?
C5 C6 . 1.381(6) ?
C6 H6A . 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 H4A N3 3_666 0.8600 2.1600 3.000(5) 167.00 yes
C3 H3B O1 2_755 0.9300 2.5400 3.182(7) 126.00 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 N1 C1 C6 . . . . -161.4(5) ?
O2 N1 C1 C6 . . . . 18.5(6) ?
O1 N1 C1 C2 . . . . 19.2(7) ?
O2 N1 C1 C2 . . . . -161.0(5) ?
C6 C1 C2 C3 . . . . -2.8(7) ?
N1 C1 C2 C3 . . . . 176.7(4) ?
C7 N2 N3 C8 . . . . 0.0(6) ?
C1 C2 C3 C4 . . . . 1.3(7) ?
C2 C3 C4 C5 . . . . 2.2(7) ?
C2 C3 C4 C7 . . . . -176.6(4) ?
C3 C4 C5 F . . . . 177.2(4) ?
C7 C4 C5 F . . . . -4.0(7) ?
C3 C4 C5 C6 . . . . -4.7(7) ?
C7 C4 C5 C6 . . . . 174.1(4) ?
F C5 C6 C1 . . . . -178.5(4) ?
C4 C5 C6 C1 . . . . 3.3(7) ?
C2 C1 C6 C5 . . . . 0.5(7) ?
N1 C1 C6 C5 . . . . -178.9(4) ?
N3 N2 C7 C4 . . . . -179.2(4) ?
N3 N2 C7 S . . . . 0.2(5) ?
C5 C4 C7 N2 . . . . -153.1(4) ?
C3 C4 C7 N2 . . . . 25.6(6) ?
C5 C4 C7 S . . . . 27.5(6) ?
C3 C4 C7 S . . . . -153.7(4) ?
C8 S C7 N2 . . . . -0.2(4) ?
C8 S C7 C4 . . . . 179.2(4) ?
N2 N3 C8 N4 . . . . -179.3(4) ?
N2 N3 C8 S . . . . -0.2(5) ?
C7 S C8 N3 . . . . 0.2(4) ?
C7 S C8 N4 . . . . 179.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742319
