#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/13/2211359.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_2211359
loop_
_publ_author_name
'Wan, Rong'
'Han, Feng'
'Wu, Feng'
'Zhang, Jin-Jun'
'Wang, Jin-Tang'
_publ_section_title
;
 5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-ylamine
;
_journal_coeditor_code           DN2063
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5547
_journal_page_last               o5548
_journal_paper_doi               10.1107/S1600536806039729
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C8 H6 F N3 S'
_chemical_formula_moiety         'C8 H6 F N3 S'
_chemical_formula_sum            'C8 H6 F N3 S'
_chemical_formula_weight         195.22
_chemical_melting_point          513
_chemical_name_systematic
;
5-(4-Fluorophenyl)-1,3,4-thiadiazol-2-ylamine
;
_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                 97.19(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8020(18)
_cell_length_b                   8.9610(18)
_cell_length_c                   11.035(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     863.5(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996),
ORTEP-3 for Windows (Farrugia, 1997)
and PLATON (Spek, 2003)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       10
_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            1810
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.9666
_exptl_absorpt_correction_T_min  0.8754
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0480
_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)+(0.0831P)²+0.1422P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                1378
_reflns_number_total             1699
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2063.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211359
_cod_database_fobs_code          2211359
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
S S 0.67382(8) 0.64217(7) 0.65161(5) 0.0479(2) Uani d . 1
F F 0.9517(3) 0.0642(2) 0.3617(2) 0.1045(8) Uani d . 1
N N1 0.6516(3) 0.6979(2) 0.42360(17) 0.0498(5) Uani d . 1
N N2 0.5926(3) 0.8231(2) 0.47480(18) 0.0526(5) Uani d . 1
N N3 0.5430(3) 0.9128(3) 0.66437(19) 0.0647(7) Uani d . 1
H H3A 0.5042 0.9942 0.6330 0.078 Uiso calc R 1
H H3B 0.5479 0.8979 0.7418 0.078 Uiso calc R 1
C C1 0.8926(4) 0.1949(3) 0.3983(3) 0.0659(8) Uani d . 1
C C2 0.9109(3) 0.3208(4) 0.3321(3) 0.0634(7) Uani d . 1
H H2 0.9639 0.3178 0.2644 0.076 Uiso calc R 1
C C3 0.8490(3) 0.4523(3) 0.3681(2) 0.0545(6) Uani d . 1
H H3 0.8611 0.5396 0.3247 0.065 Uiso calc R 1
C C4 0.7685(3) 0.4555(3) 0.4690(2) 0.0434(5) Uani d . 1
C C5 0.7544(3) 0.3254(3) 0.5345(2) 0.0541(6) Uani d . 1
H H5 0.7034 0.3274 0.6034 0.065 Uiso calc R 1
C C6 0.8154(4) 0.1928(3) 0.4984(3) 0.0682(8) Uani d . 1
H H6 0.8042 0.1047 0.5410 0.082 Uiso calc R 1
C C7 0.6987(3) 0.5958(3) 0.50219(19) 0.0421(5) Uani d . 1
C C8 0.5957(3) 0.8094(3) 0.5929(2) 0.0454(5) 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 0.0684(4) 0.0426(4) 0.0327(3) 0.0115(3) 0.0057(3) 0.0049(2)
F 0.1419(19) 0.0732(13) 0.1000(15) 0.0494(13) 0.0213(13) -0.0206(11)
N1 0.0748(13) 0.0407(11) 0.0340(10) 0.0096(10) 0.0075(9) 0.0009(8)
N2 0.0832(15) 0.0391(11) 0.0347(10) 0.0134(10) 0.0045(10) 0.0031(8)
N3 0.1062(19) 0.0526(13) 0.0340(10) 0.0287(13) 0.0030(11) -0.0025(9)
C1 0.0777(19) 0.0557(16) 0.0631(17) 0.0241(15) 0.0043(14) -0.0160(14)
C2 0.0644(17) 0.0737(19) 0.0531(15) 0.0136(14) 0.0112(13) -0.0101(14)
C3 0.0628(16) 0.0521(15) 0.0492(14) 0.0045(12) 0.0097(12) 0.0011(11)
C4 0.0495(13) 0.0405(12) 0.0395(11) 0.0032(10) 0.0021(9) -0.0027(10)
C5 0.0695(16) 0.0432(14) 0.0503(14) 0.0091(12) 0.0111(12) 0.0047(11)
C6 0.091(2) 0.0430(14) 0.0710(18) 0.0145(14) 0.0110(16) 0.0054(13)
C7 0.0540(13) 0.0379(12) 0.0337(11) 0.0014(10) 0.0031(9) 0.0007(9)
C8 0.0609(14) 0.0388(12) 0.0351(11) 0.0076(10) 0.0003(10) 0.0021(9)
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
C8 S C7 86.75(11)
C7 N1 N2 113.85(18)
C8 N2 N1 111.63(19)
C8 N3 H3A 120.0
C8 N3 H3B 120.0
H3A N3 H3B 120.0
F C1 C2 118.5(3)
F C1 C6 118.3(3)
C2 C1 C6 123.2(3)
C1 C2 C3 118.4(2)
C1 C2 H2 120.8
C3 C2 H2 120.8
C2 C3 C4 120.4(2)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 119.2(2)
C5 C4 C7 121.5(2)
C3 C4 C7 119.2(2)
C6 C5 C4 120.6(3)
C6 C5 H5 119.7
C4 C5 H5 119.7
C1 C6 C5 118.1(3)
C1 C6 H6 121.0
C5 C6 H6 121.0
N1 C7 C4 123.3(2)
N1 C7 S 113.51(17)
C4 C7 S 123.23(17)
N2 C8 N3 123.9(2)
N2 C8 S 114.25(18)
N3 C8 S 121.82(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S C8 1.740(2)
S C7 1.741(2)
F C1 1.363(3)
N1 C7 1.293(3)
N1 N2 1.386(3)
N2 C8 1.306(3)
N3 C8 1.337(3)
N3 H3A 0.8600
N3 H3B 0.8600
C1 C2 1.364(4)
C1 C6 1.368(4)
C2 C3 1.378(4)
C2 H2 0.9300
C3 C4 1.392(3)
C3 H3 0.9300
C4 C5 1.385(3)
C4 C7 1.467(3)
C5 C6 1.383(4)
C5 H5 0.9300
C6 H6 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
N3 H3B N1 4_576 0.86 2.27 3.065(3) 154.5
N3 H3A N2 3_676 0.86 2.14 2.987(3) 170.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 481931
