#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:21:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180423 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/92/7209279.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_7209279
loop_
_publ_author_name
'Hoser, Anna A.'
'Kamiński, Daniel M.'
'Matwijczuk, Arkadiusz'
'Niewiadomy, Andrzej'
'Gagoś, Mariusz'
'Woźniak, Krzysztof'
_publ_section_title
;
 On polymorphism of
 2-(4-fluorophenylamino)-5-(2,4-dihydroxybenzeno)-1,3,4-thiadiazole (FABT)
 DMSO solvates
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              1978
_journal_paper_doi               10.1039/c3ce26778d
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C16 H16 F N3 O3 S2'
_chemical_formula_weight         381.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.410(5)
_cell_angle_beta                 86.768(5)
_cell_angle_gamma                82.386(5)
_cell_formula_units_Z            2
_cell_length_a                   6.4038(4)
_cell_length_b                   10.2494(6)
_cell_length_c                   13.1644(9)
_cell_measurement_temperature    100(2)
_cell_volume                     835.50(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10808
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.351
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0451P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2074
_reflns_number_total             2949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce26778d.txt
_cod_data_source_block           shelxl
_cod_database_code               7209279
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
H1N H 0.162(4) 0.084(3) 0.983(2) 0.028(8) Uiso 1 1 d .
H2O H -0.194(5) -0.170(3) 0.718(2) 0.046(11) Uiso 1 1 d .
H1O H -0.039(5) -0.279(3) 0.341(2) 0.055(10) Uiso 1 1 d .
S1 S 0.33382(9) 0.00848(6) 0.74641(5) 0.01609(17) Uani 1 1 d .
S2 S 0.72924(11) 0.50582(7) 1.34089(5) 0.0280(2) Uani 1 1 d .
F1 F 0.8581(2) 0.39603(15) 0.98340(11) 0.0313(4) Uani 1 1 d .
N3 N -0.0018(3) -0.10325(19) 0.79722(15) 0.0168(5) Uani 1 1 d .
O2 O -0.2260(3) -0.18987(18) 0.67072(14) 0.0213(4) Uani 1 1 d .
O1 O 0.0878(3) -0.25366(18) 0.34711(13) 0.0239(4) Uani 1 1 d .
N2 N 0.0285(3) -0.04343(19) 0.87850(15) 0.0170(5) Uani 1 1 d .
N1 N 0.2423(3) 0.0883(2) 0.93429(17) 0.0175(5) Uani 1 1 d .
C14 C 0.2990(4) -0.1321(2) 0.55359(18) 0.0166(5) Uani 1 1 d .
H14 H 0.4256 -0.1012 0.5678 0.020 Uiso 1 1 calc R
C8 C 0.1405(4) -0.0857(2) 0.72201(18) 0.0145(5) Uani 1 1 d .
C2 C 0.5303(4) 0.3164(2) 1.03331(19) 0.0211(6) Uani 1 1 d .
H2 H 0.5134 0.3660 1.0869 0.025 Uiso 1 1 calc R
C9 C 0.1300(4) -0.1340(2) 0.62644(17) 0.0138(5) Uani 1 1 d .
C7 C 0.1966(4) 0.0201(2) 0.86268(17) 0.0136(5) Uani 1 1 d .
O1S O 0.7262(3) 0.65585(17) 1.33001(14) 0.0344(5) Uani 1 1 d .
C5 C 0.5827(4) 0.1741(2) 0.87486(18) 0.0175(6) Uani 1 1 d .
H5 H 0.6004 0.1263 0.8201 0.021 Uiso 1 1 calc R
C10 C -0.0552(4) -0.1806(2) 0.60382(18) 0.0153(5) Uani 1 1 d .
C12 C 0.0971(4) -0.2159(2) 0.43953(18) 0.0171(6) Uani 1 1 d .
C11 C -0.0711(4) -0.2198(2) 0.51017(18) 0.0167(5) Uani 1 1 d .
H11 H -0.1978 -0.2493 0.4947 0.020 Uiso 1 1 calc R
C4 C 0.4038(4) 0.1661(2) 0.93975(18) 0.0146(5) Uani 1 1 d .
C3 C 0.3791(4) 0.2392(2) 1.01913(18) 0.0192(6) Uani 1 1 d .
H3 H 0.2567 0.2352 1.0634 0.023 Uiso 1 1 calc R
C6 C 0.7355(4) 0.2517(2) 0.88978(18) 0.0185(6) Uani 1 1 d .
H6 H 0.8585 0.2569 0.8460 0.022 Uiso 1 1 calc R
C13 C 0.2847(4) -0.1742(2) 0.46171(18) 0.0177(6) Uani 1 1 d .
H13 H 0.4018 -0.1747 0.4141 0.021 Uiso 1 1 calc R
C1 C 0.7062(4) 0.3204(2) 0.96859(19) 0.0197(6) Uani 1 1 d .
C2S C 0.8161(5) 0.4754(3) 1.2172(2) 0.0383(8) Uani 1 1 d .
H23S H 0.9664 0.4852 1.2066 0.058 Uiso 1 1 calc R
H22S H 0.7361 0.5403 1.1629 0.058 Uiso 1 1 calc R
H21S H 0.7940 0.3838 1.2135 0.058 Uiso 1 1 calc R
C1S C 0.4612(4) 0.4817(3) 1.3372(3) 0.0449(8) Uani 1 1 d .
H11S H 0.4506 0.3856 1.3441 0.067 Uiso 1 1 calc R
H13S H 0.4027 0.5322 1.2708 0.067 Uiso 1 1 calc R
H12S H 0.3819 0.5139 1.3947 0.067 Uiso 1 1 calc R
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
C7 S1 C8 87.12(11)
O1S S2 C2S 104.77(12)
O1S S2 C1S 104.81(12)
C2S S2 C1S 99.17(16)
C8 N3 N2 114.24(19)
C7 N2 N3 111.93(18)
C7 N1 C4 132.6(2)
C13 C14 C9 121.2(2)
N3 C8 C9 122.8(2)
N3 C8 S1 112.66(17)
C9 C8 S1 124.48(17)
C3 C2 C1 118.8(2)
C14 C9 C10 118.3(2)
C14 C9 C8 121.8(2)
C10 C9 C8 119.9(2)
N2 C7 N1 118.7(2)
N2 C7 S1 114.03(17)
N1 C7 S1 127.28(18)
C6 C5 C4 120.2(2)
O2 C10 C11 116.9(2)
O2 C10 C9 122.8(2)
C11 C10 C9 120.4(2)
O1 C12 C11 121.9(2)
O1 C12 C13 117.6(2)
C11 C12 C13 120.5(2)
C12 C11 C10 120.1(2)
C5 C4 N1 125.4(2)
C5 C4 C3 119.0(2)
N1 C4 C3 115.6(2)
C2 C3 C4 120.6(2)
C1 C6 C5 118.9(2)
C14 C13 C12 119.4(2)
C6 C1 F1 118.7(2)
C6 C1 C2 122.5(2)
F1 C1 C2 118.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.740(2)
S1 C8 1.751(2)
S2 O1S 1.5106(18)
S2 C2S 1.770(3)
S2 C1S 1.771(3)
F1 C1 1.368(3)
N3 C8 1.307(3)
N3 N2 1.378(2)
O2 C10 1.365(3)
O1 C12 1.361(3)
N2 C7 1.314(3)
N1 C7 1.355(3)
N1 C4 1.401(3)
C14 C13 1.381(3)
C14 C9 1.404(3)
C8 C9 1.457(3)
C2 C3 1.373(3)
C2 C1 1.373(3)
C9 C10 1.405(3)
C5 C6 1.387(3)
C5 C4 1.390(3)
C10 C11 1.390(3)
C12 C11 1.382(3)
C12 C13 1.393(3)
C4 C3 1.403(3)
C6 C1 1.367(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O N3 0.75(3) 1.93(3) 2.622(3) 153(3) .
O1 H1O O1S 0.90(3) 1.75(3) 2.644(3) 174(3) 1_444
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
C8 N3 N2 C7 0.3(3)
N2 N3 C8 C9 -176.26(19)
N2 N3 C8 S1 0.6(2)
C7 S1 C8 N3 -0.97(18)
C7 S1 C8 C9 175.9(2)
C13 C14 C9 C10 0.3(3)
C13 C14 C9 C8 -178.0(2)
N3 C8 C9 C14 -170.4(2)
S1 C8 C9 C14 13.1(3)
N3 C8 C9 C10 11.4(3)
S1 C8 C9 C10 -165.08(17)
N3 N2 C7 N1 177.52(19)
N3 N2 C7 S1 -1.0(2)
C4 N1 C7 N2 -178.9(2)
C4 N1 C7 S1 -0.5(4)
C8 S1 C7 N2 1.13(18)
C8 S1 C7 N1 -177.3(2)
C14 C9 C10 O2 178.2(2)
C8 C9 C10 O2 -3.6(3)
C14 C9 C10 C11 -1.8(3)
C8 C9 C10 C11 176.4(2)
O1 C12 C11 C10 179.9(2)
C13 C12 C11 C10 0.7(3)
O2 C10 C11 C12 -178.6(2)
C9 C10 C11 C12 1.4(3)
C6 C5 C4 N1 -178.0(2)
C6 C5 C4 C3 1.0(3)
C7 N1 C4 C5 -10.8(4)
C7 N1 C4 C3 170.1(2)
C1 C2 C3 C4 -0.2(4)
C5 C4 C3 C2 -0.7(3)
N1 C4 C3 C2 178.4(2)
C4 C5 C6 C1 -0.5(3)
C9 C14 C13 C12 1.8(3)
O1 C12 C13 C14 178.5(2)
C11 C12 C13 C14 -2.3(3)
C5 C6 C1 F1 179.6(2)
C5 C6 C1 C2 -0.4(4)
C3 C2 C1 C6 0.8(4)
C3 C2 C1 F1 -179.2(2)
