##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section C, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 1898375'
_audit_creation_method     'SHELXL-2016/6'
_chemical_name_systematic
;\
(5-Amino-3-methylsulfanyl-1H-1,2,4-triazol-1-yl)(2-fluorophenyl)\
methanon
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H9 F N4 O S'
_chemical_formula_sum     'C10 H9 F N4 O S'
_chemical_formula_iupac     'C10 H9 F N4 O S'
_chemical_formula_weight     252.27
_chemical_melting_point     ?
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.6599(9)
_cell_length_b     7.8079(8)
_cell_length_c     10.0140(12)
_cell_angle_alpha     94.487(9)
_cell_angle_beta     108.668(11)
_cell_angle_gamma     97.565(9)
_cell_volume     557.83(12)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5358
_cell_measurement_theta_min     3.5530
_cell_measurement_theta_max     27.4530
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'parallelepiped'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.380
_exptl_crystal_size_mid     0.340
_exptl_crystal_size_min     0.220
_exptl_crystal_density_diffrn     1.502
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     260
_exptl_absorpt_coefficient_mu     0.292
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_absorpt_correction_T_min     0.85591
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     298(2)
_diffrn_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
;
Agilent SuperNova Dual Source diffractometer with an Atlas detector'
;
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'CCD plate'
_diffrn_detector_area_resol_mean     5.3072
_diffrn_reflns_number     12256
_diffrn_reflns_av_R_equivalents     0.0441
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_theta_min     2.846
_diffrn_reflns_theta_max     27.097
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_refine_special_details     ?
_reflns_number_total     2450
_reflns_number_gt     2107
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0491
_refine_ls_R_factor_gt     0.0424
_refine_ls_wR_factor_gt     0.1100
_refine_ls_wR_factor_ref     0.1164
_refine_ls_goodness_of_fit_ref     0.892
_refine_ls_restrained_S_all     0.875
_refine_ls_number_reflns     2450
_refine_ls_number_parameters     225
_refine_ls_number_restraints     159
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0563P)²+0.4216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.273
_refine_diff_density_min     -0.218
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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 1.02515(8) 0.25941(8) 1.09852(5) 0.05278(19) Uani d 1 . .
    H H1 1.373(3) 0.476(3) 0.7053(6) 0.063 Uiso d 1 . .
    H H2 1.4957(16) 0.518(3) 0.8587(18) 0.063 Uiso d 1 . .
    C C10A 0.8191(3) 0.2346(10) 0.5115(8) 0.0367(4) Uani d 0.633(3) A 1
    C C11A 0.7667(7) 0.1073(11) 0.3944(7) 0.0377(5) Uani d 0.633(3) A 1
    C C12A 0.5846(5) 0.0481(9) 0.3128(7) 0.0465(12) Uani d 0.633(3) A 1
    H H12A 0.554375 -0.037357 0.235294 0.056 Uiso calc 0.633(3) A 1
    C C13A 0.4464(5) 0.1184(5) 0.3483(4) 0.0399(5) Uani d 0.633(3) A 1
    H H13A 0.321606 0.079988 0.294066 0.048 Uiso calc 0.633(3) A 1
    C C14A 0.4925(5) 0.2463(5) 0.4645(4) 0.0391(4) Uani d 0.633(3) A 1
    H H14A 0.399095 0.295157 0.486343 0.047 Uiso calc 0.633(3) A 1
    C C15A 0.6781(2) 0.3005(7) 0.5474(5) 0.0380(4) Uani d 0.633(3) A 1
    H H15A 0.708397 0.381670 0.627779 0.046 Uiso calc 0.633(3) A 1
    F F1A 0.9121(3) 0.0504(3) 0.3615(2) 0.0532(6) Uani d 0.633(3) A 1
    C C10B 0.8175(4) 0.2377(16) 0.5144(14) 0.0371(4) Uani d 0.367(3) A 2
    C C11B 0.7981(9) 0.1168(17) 0.3994(10) 0.0371(16) Uani d 0.367(3) A 2
    H H11B 0.903845 0.091889 0.380400 0.045 Uiso calc 0.367(3) A 2
    C C12B 0.6220(13) 0.0324(17) 0.3122(13) 0.0390(5) Uani d 0.367(3) A 2
    H H12B 0.612361 -0.055916 0.241001 0.047 Uiso calc 0.367(3) A 2
    C C13B 0.4644(11) 0.0767(9) 0.3292(7) 0.0394(5) Uani d 0.367(3) A 2
    H H13B 0.347918 0.018856 0.269960 0.047 Uiso calc 0.367(3) A 2
    C C14B 0.4765(9) 0.2065(9) 0.4335(7) 0.0389(4) Uani d 0.367(3) A 2
    H H14B 0.368949 0.241264 0.442838 0.047 Uiso calc 0.367(3) A 2
    C C15B 0.6519(3) 0.2856(12) 0.5254(8) 0.0380(4) Uani d 0.367(3) A 2
    F F1B 0.6863(5) 0.4163(5) 0.6360(4) 0.0557(11) Uani d 0.367(3) A 2
    N N3 0.9653(2) 0.2605(2) 0.81764(16) 0.0400(4) Uani d 1 . .
    N N4 1.0763(2) 0.3271(2) 0.74015(16) 0.0392(4) Uani d 1 . .
    C C5 1.2529(3) 0.3998(3) 0.8343(2) 0.0426(4) Uani d 1 . .
    N N6 1.2581(2) 0.3836(2) 0.96490(18) 0.0466(4) Uani d 1 . .
    N N7 1.3908(3) 0.4744(3) 0.7944(2) 0.0603(5) Uani d 1 . .
    C C2 1.0807(3) 0.3004(3) 0.9475(2) 0.0412(4) Uani d 1 . .
    C C8 1.01785(18) 0.3102(2) 0.59287(17) 0.0372(4) Uani d 1 . .
    O O9 1.12866(18) 0.3549(2) 0.53342(15) 0.0490(4) Uani d 1 . .
    C C18 0.7830(3) 0.1643(3) 1.0186(2) 0.0593(6) Uani d 1 . .
    H H18A 0.724733 0.160853 1.090360 0.089 Uiso calc 1 . .
    H H18B 0.773136 0.047986 0.974666 0.089 Uiso calc 1 . .
    H H18C 0.721750 0.233088 0.948057 0.089 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 . 1.739(2) ?
    S1 C18 . 1.796(2) ?
    C10A C15A . 1.388(5) ?
    C10A C11A . 1.391(5) ?
    C10A C8 . 1.491(2) ?
    C11A C12A . 1.367(6) ?
    C11A F1A . 1.374(6) ?
    C12A C13A . 1.382(5) ?
    C12A H12A . 0.9300 ?
    C13A C14A . 1.392(4) ?
    C13A H13A . 0.9300 ?
    C14A C15A . 1.386(4) ?
    C14A H14A . 0.9300 ?
    C15A H15A . 0.9300 ?
    C10B C11B . 1.386(9) ?
    C10B C15B . 1.403(7) ?
    C10B C8 . 1.491(2) ?
    C11B C12B . 1.392(10) ?
    C11B H11B . 0.9300 ?
    C12B C13B . 1.356(9) ?
    C12B H12B . 0.9300 ?
    C13B C14B . 1.369(7) ?
    C13B H13B . 0.9300 ?
    C14B C15B . 1.391(6) ?
    C14B H14B . 0.9300 ?
    C15B F1B . 1.380(8) ?
    N3 C2 . 1.303(2) ?
    N3 N4 . 1.402(2) ?
    N4 C8 . 1.387(2) ?
    N4 C5 . 1.393(2) ?
    C5 N6 . 1.312(3) ?
    C5 N7 . 1.326(3) ?
    N6 C2 . 1.377(2) ?
    N7 H1 . 0.8600(11) ?
    N7 H2 . 0.8600(11) ?
    C8 O9 . 1.214(2) ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
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
    C2 S1 C18 . . 100.21(10) ?
    C15A C10A C11A . . 117.7(3) ?
    C15A C10A C8 . . 119.2(3) ?
    C11A C10A C8 . . 123.0(4) ?
    C12A C11A F1A . . 121.8(4) ?
    C12A C11A C10A . . 123.0(5) ?
    F1A C11A C10A . . 115.2(3) ?
    C11A C12A C13A . . 118.4(5) ?
    C11A C12A H12A . . 120.8 ?
    C13A C12A H12A . . 120.8 ?
    C12A C13A C14A . . 120.5(4) ?
    C12A C13A H13A . . 119.7 ?
    C14A C13A H13A . . 119.7 ?
    C15A C14A C13A . . 119.8(3) ?
    C15A C14A H14A . . 120.1 ?
    C13A C14A H14A . . 120.1 ?
    C14A C15A C10A . . 120.5(3) ?
    C14A C15A H15A . . 119.7 ?
    C10A C15A H15A . . 119.7 ?
    C11B C10B C15B . . 116.3(5) ?
    C11B C10B C8 . . 111.4(5) ?
    C15B C10B C8 . . 131.7(6) ?
    C10B C11B C12B . . 120.7(7) ?
    C10B C11B H11B . . 119.6 ?
    C12B C11B H11B . . 119.6 ?
    C13B C12B C11B . . 121.1(10) ?
    C13B C12B H12B . . 119.4 ?
    C11B C12B H12B . . 119.4 ?
    C12B C13B C14B . . 120.1(7) ?
    C12B C13B H13B . . 120.0 ?
    C14B C13B H13B . . 120.0 ?
    C13B C14B C15B . . 119.0(6) ?
    C13B C14B H14B . . 120.5 ?
    C15B C14B H14B . . 120.5 ?
    F1B C15B C14B . . 125.7(4) ?
    F1B C15B C10B . . 112.1(4) ?
    C14B C15B C10B . . 122.2(6) ?
    C2 N3 N4 . . 101.36(14) ?
    C8 N4 C5 . . 127.12(15) ?
    C8 N4 N3 . . 123.84(14) ?
    C5 N4 N3 . . 108.91(15) ?
    N6 C5 N7 . . 126.71(18) ?
    N6 C5 N4 . . 109.42(16) ?
    N7 C5 N4 . . 123.86(18) ?
    C5 N6 C2 . . 103.34(16) ?
    C5 N7 H1 . . 119.0(17) ?
    C5 N7 H2 . . 118.8(17) ?
    H1 N7 H2 . . 122(2) ?
    N3 C2 N6 . . 116.95(17) ?
    N3 C2 S1 . . 124.73(15) ?
    N6 C2 S1 . . 118.31(14) ?
    O9 C8 N4 . . 119.78(14) ?
    O9 C8 C10B . . 122.9(6) ?
    N4 C8 C10B . . 117.4(6) ?
    O9 C8 C10A . . 121.7(4) ?
    N4 C8 C10A . . 118.5(4) ?
    S1 C18 H18A . . 109.5 ?
    S1 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    S1 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
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
    C15A C10A C11A C12A . . . . 1.4(15) ?
    C8 C10A C11A C12A . . . . -174.5(8) ?
    C15A C10A C11A F1A . . . . 178.3(8) ?
    C8 C10A C11A F1A . . . . 2.4(14) ?
    F1A C11A C12A C13A . . . . -176.6(7) ?
    C10A C11A C12A C13A . . . . 0.1(14) ?
    C11A C12A C13A C14A . . . . 0.0(9) ?
    C12A C13A C14A C15A . . . . -1.6(7) ?
    C13A C14A C15A C10A . . . . 3.2(8) ?
    C11A C10A C15A C14A . . . . -3.1(12) ?
    C8 C10A C15A C14A . . . . 173.0(6) ?
    C15B C10B C11B C12B . . . . -8(2) ?
    C8 C10B C11B C12B . . . . 179.6(13) ?
    C10B C11B C12B C13B . . . . 6(2) ?
    C11B C12B C13B C14B . . . . 0.0(17) ?
    C12B C13B C14B C15B . . . . -3.1(12) ?
    C13B C14B C15B F1B . . . . -179.4(8) ?
    C13B C14B C15B C10B . . . . 0.4(15) ?
    C11B C10B C15B F1B . . . . -175.0(13) ?
    C8 C10B C15B F1B . . . . -5(2) ?
    C11B C10B C15B C14B . . . . 5(2) ?
    C8 C10B C15B C14B . . . . 175.4(12) ?
    C2 N3 N4 C8 . . . . 177.04(17) ?
    C2 N3 N4 C5 . . . . 0.9(2) ?
    C8 N4 C5 N6 . . . . -176.37(18) ?
    N3 N4 C5 N6 . . . . -0.4(2) ?
    C8 N4 C5 N7 . . . . 4.2(3) ?
    N3 N4 C5 N7 . . . . -179.8(2) ?
    N7 C5 N6 C2 . . . . 179.1(2) ?
    N4 C5 N6 C2 . . . . -0.3(2) ?
    N4 N3 C2 N6 . . . . -1.2(2) ?
    N4 N3 C2 S1 . . . . 177.63(14) ?
    C5 N6 C2 N3 . . . . 1.0(2) ?
    C5 N6 C2 S1 . . . . -177.93(15) ?
    C18 S1 C2 N3 . . . . -1.9(2) ?
    C18 S1 C2 N6 . . . . 176.86(17) ?
    C5 N4 C8 O9 . . . . 3.3(3) ?
    N3 N4 C8 O9 . . . . -172.11(17) ?
    C5 N4 C8 C10B . . . . -176.2(6) ?
    N3 N4 C8 C10B . . . . 8.4(6) ?
    C5 N4 C8 C10A . . . . -177.5(4) ?
    N3 N4 C8 C10A . . . . 7.1(4) ?
    C11B C10B C8 O9 . . . . 44.0(16) ?
    C15B C10B C8 O9 . . . . -126.6(15) ?
    C11B C10B C8 N4 . . . . -136.5(11) ?
    C15B C10B C8 N4 . . . . 52.9(19) ?
    C15A C10A C8 O9 . . . . -130.7(7) ?
    C11A C10A C8 O9 . . . . 45.2(11) ?
    C15A C10A C8 N4 . . . . 50.1(9) ?
    C11A C10A C8 N4 . . . . -134.0(8) ?
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
    N7 H1 O9 . 0.8600(11) 2.14(2) 2.738(2) 126(2)
    C15A H15A N3 . 0.93 2.60 2.960(5) 104
    N7 H2 N6 2_867 0.859(17) 2.131(17) 2.987(3) 173.6(17)
    C14A H14A O9 1_455 0.93 2.36 3.275(4) 167
_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     0.897
_shelx_estimated_absorpt_T_max     0.939
data_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 1898376'
_audit_creation_method     'SHELXL-2016/6'
_chemical_name_systematic
;
2-Fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H9 F N4 O S'
_chemical_formula_sum     'C10 H9 F N4 O S'
_chemical_formula_iupac     'C10 H9 F N4 O S'
_chemical_formula_weight     252.27
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    'x+1/2, -y+1/2, z+1/2'
    '-x, -y, -z'
    '-x-1/2, y-1/2, -z-1/2'
_cell_length_a     5.0509(11)
_cell_length_b     26.640(5)
_cell_length_c     8.0251(16)
_cell_angle_alpha     90
_cell_angle_beta     94.12(2)
_cell_angle_gamma     90
_cell_volume     1077.0(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3138
_cell_measurement_theta_min     3.9540
_cell_measurement_theta_max     24.7370
_cell_measurement_temperature     298(2)
_exptl_crystal_description     'parallelepiped'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.228
_exptl_crystal_size_mid     0.078
_exptl_crystal_size_min     0.053
_exptl_crystal_density_diffrn     1.556
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.303
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_absorpt_correction_T_min     0.73397
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     298(2)
_diffrn_source     'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type
;
Agilent SuperNova Dual Source diffractometer with an Atlas detector
;
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'CCD plate'
_diffrn_detector_area_resol_mean     5.3072
_diffrn_reflns_number     5060
_diffrn_reflns_av_R_equivalents     0.080
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_theta_min     3.059
_diffrn_reflns_theta_max     26.770
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.977
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     6
_diffrn_reflns_limit_k_min     -33
_diffrn_reflns_limit_k_max     33
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     9
_refine_special_details
;
Refined as a 3-component twin
;
_reflns_number_total     5060
_reflns_number_gt     3267
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1032
_refine_ls_R_factor_gt     0.0711
_refine_ls_wR_factor_gt     0.2253
_refine_ls_wR_factor_ref     0.2371
_refine_ls_goodness_of_fit_ref     1.103
_refine_ls_restrained_S_all     1.103
_refine_ls_number_reflns     5060
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.1329P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.290
_refine_diff_density_min     -0.375
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'S' 'S' 0.1246 0.1234
                         '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'
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
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 0.1477(4) 0.27586(4) 0.0007(2) 0.0449(5) Uani d 1 . .
    F F1 0.1660(7) 0.53895(10) 0.1032(4) 0.0505(9) Uani d 1 . .
    H H1 0.223(15) 0.461(2) 0.206(8) 0.06(2) Uiso d 1 . .
    O O1 0.8265(8) 0.46221(12) 0.2805(5) 0.0404(10) Uani d 1 . .
    N N1 0.5883(9) 0.32664(13) 0.1083(6) 0.0357(11) Uani d 1 . .
    C C1 0.4195(13) 0.23505(19) -0.0417(9) 0.0544(18) Uani d 1 . .
    H H1A 0.351155 0.204771 -0.093496 0.082 Uiso calc 1 . .
    H H1B 0.519322 0.226953 0.061054 0.082 Uiso calc 1 . .
    H H1C 0.532742 0.251692 -0.115383 0.082 Uiso calc 1 . .
    C C2 0.3270(11) 0.32716(16) 0.0838(6) 0.0303(11) Uani d 1 . .
    N N2 0.6408(10) 0.37462(14) 0.1623(6) 0.0344(11) Uani d 1 . .
    C C3 0.4156(10) 0.40049(16) 0.1636(6) 0.0301(12) Uani d 1 . .
    N N3 0.2102(9) 0.37196(14) 0.1168(6) 0.0358(11) Uani d 1 . .
    C C4 0.6041(11) 0.48003(17) 0.2559(6) 0.0307(12) Uani d 1 . .
    H H4 0.81(2) 0.386(3) 0.187(12) 0.11(3) Uiso d 1 . .
    N N4 0.3965(9) 0.45071(14) 0.1992(6) 0.0342(10) Uani d 1 . .
    C C6 0.3445(12) 0.56183(17) 0.2127(7) 0.0361(13) Uani d 1 . .
    C C5 0.5514(10) 0.53388(16) 0.2864(6) 0.0305(12) Uani d 1 . .
    C C7 0.3142(13) 0.61226(18) 0.2366(7) 0.0448(15) Uani d 1 . .
    H H7 0.173297 0.629657 0.182589 0.054 Uiso calc 1 . .
    C C9 0.7035(14) 0.60997(19) 0.4223(8) 0.0497(16) Uani d 1 . .
    H H9 0.824367 0.626244 0.496651 0.060 Uiso calc 1 . .
    C C8 0.4989(14) 0.63664(19) 0.3431(8) 0.0520(17) Uani d 1 . .
    H H8 0.484520 0.670992 0.361139 0.062 Uiso calc 1 . .
    C C10 0.7318(12) 0.55995(18) 0.3933(7) 0.0388(13) Uani d 1 . .
    H H10 0.874783 0.542851 0.446041 0.047 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C2 . 1.746(5) ?
    S1 C1 . 1.803(6) ?
    F1 C6 . 1.357(6) ?
    O1 C4 . 1.222(6) ?
    N1 C2 . 1.320(7) ?
    N1 N2 . 1.370(6) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 N3 . 1.366(6) ?
    N2 C3 . 1.331(7) ?
    N2 H4 . 0.90(10) ?
    C3 N3 . 1.319(7) ?
    C3 N4 . 1.373(6) ?
    C4 N4 . 1.360(7) ?
    C4 C5 . 1.483(7) ?
    N4 H1 . 0.93(7) ?
    C6 C7 . 1.367(7) ?
    C6 C5 . 1.381(7) ?
    C5 C10 . 1.391(7) ?
    C7 C8 . 1.381(9) ?
    C7 H7 . 0.9300 ?
    C9 C10 . 1.362(7) ?
    C9 C8 . 1.372(9) ?
    C9 H9 . 0.9300 ?
    C8 H8 . 0.9300 ?
    C10 H10 . 0.9300 ?
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
    C2 S1 C1 . . 99.4(3) ?
    C2 N1 N2 . . 101.9(4) ?
    S1 C1 H1A . . 109.5 ?
    S1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    S1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 N3 . . 114.9(4) ?
    N1 C2 S1 . . 122.3(3) ?
    N3 C2 S1 . . 122.6(4) ?
    C3 N2 N1 . . 109.8(4) ?
    C3 N2 H4 . . 128(5) ?
    N1 N2 H4 . . 122(5) ?
    N3 C3 N2 . . 110.8(4) ?
    N3 C3 N4 . . 123.7(5) ?
    N2 C3 N4 . . 125.4(5) ?
    C3 N3 C2 . . 102.5(4) ?
    O1 C4 N4 . . 120.6(4) ?
    O1 C4 C5 . . 121.5(5) ?
    N4 C4 C5 . . 117.9(5) ?
    C4 N4 C3 . . 124.4(5) ?
    C4 N4 H1 . . 121(4) ?
    C3 N4 H1 . . 113(4) ?
    F1 C6 C7 . . 117.2(5) ?
    F1 C6 C5 . . 118.8(4) ?
    C7 C6 C5 . . 124.0(5) ?
    C6 C5 C10 . . 115.9(4) ?
    C6 C5 C4 . . 126.2(5) ?
    C10 C5 C4 . . 117.9(5) ?
    C6 C7 C8 . . 118.1(6) ?
    C6 C7 H7 . . 120.9 ?
    C8 C7 H7 . . 120.9 ?
    C10 C9 C8 . . 120.8(6) ?
    C10 C9 H9 . . 119.6 ?
    C8 C9 H9 . . 119.6 ?
    C9 C8 C7 . . 119.7(5) ?
    C9 C8 H8 . . 120.1 ?
    C7 C8 H8 . . 120.1 ?
    C9 C10 C5 . . 121.4(5) ?
    C9 C10 H10 . . 119.3 ?
    C5 C10 H10 . . 119.3 ?
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
    N2 N1 C2 N3 . . . . 0.6(6) ?
    N2 N1 C2 S1 . . . . 176.0(4) ?
    C1 S1 C2 N1 . . . . -3.9(5) ?
    C1 S1 C2 N3 . . . . 171.2(4) ?
    C2 N1 N2 C3 . . . . -1.3(5) ?
    N1 N2 C3 N3 . . . . 1.6(6) ?
    N1 N2 C3 N4 . . . . -175.0(4) ?
    N2 C3 N3 C2 . . . . -1.2(5) ?
    N4 C3 N3 C2 . . . . 175.5(5) ?
    N1 C2 N3 C3 . . . . 0.3(6) ?
    S1 C2 N3 C3 . . . . -175.0(4) ?
    O1 C4 N4 C3 . . . . -0.8(8) ?
    C5 C4 N4 C3 . . . . 179.2(4) ?
    N3 C3 N4 C4 . . . . 176.4(5) ?
    N2 C3 N4 C4 . . . . -7.4(8) ?
    F1 C6 C5 C10 . . . . 178.1(5) ?
    C7 C6 C5 C10 . . . . 1.4(8) ?
    F1 C6 C5 C4 . . . . 1.2(8) ?
    C7 C6 C5 C4 . . . . -175.5(5) ?
    O1 C4 C5 C6 . . . . 155.9(5) ?
    N4 C4 C5 C6 . . . . -24.1(7) ?
    O1 C4 C5 C10 . . . . -21.0(7) ?
    N4 C4 C5 C10 . . . . 159.0(5) ?
    F1 C6 C7 C8 . . . . -177.9(5) ?
    C5 C6 C7 C8 . . . . -1.2(8) ?
    C10 C9 C8 C7 . . . . 2.0(9) ?
    C6 C7 C8 C9 . . . . -0.6(9) ?
    C8 C9 C10 C5 . . . . -1.7(9) ?
    C6 C5 C10 C9 . . . . 0.0(8) ?
    C4 C5 C10 C9 . . . . 177.2(5) ?
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
    N4 H1 F1 . 0.92(7) 2.25(6) 2.710(5) 111(5)
    N2 H4 O1 . 0.92(10) 2.16(8) 2.664(5) 114(7)
    N4 H1 O1 1_455 0.92(7) 2.13(8) 3.013(6) 159(5)
    N2 H4 N3 1_655 0.92(10) 2.17(10) 2.926(7) 140(8)
    C10 H10 O1 3_766 0.93 2.58 3.367(7) 143
    C1 H1A N1 2_454 0.96 2.78 3.566(8) 140
_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     0.934
_shelx_estimated_absorpt_T_max     0.984
data_global
_journal_date_recd_electronic     2018-12-18
_journal_date_accepted     2019-02-20
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2019
_journal_volume     75
_journal_issue      3
_journal_page_first     359
_journal_page_last     371
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229619002572
_journal_coeditor_code     YO3062
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Mario A. Macías'
;
Department of Chemistry
Universidad de los Andes
Cra. 1 N 18-A-12
111711 Bogotá
Colombia
;
 'ma.maciasl@uniandes.edu.co'
    'Moreno-Fuquen, Rodolfo'
;
Department of Chemistry
Universidad del Valle
AA 25360
Santiago de Cali
Colombia
;
 'rodolfo.moreno@correounivalle.edu.co'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Catalyst- and solvent-free synthesis of
2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide
through a microwave-assisted Fries rearrangement: X-ray structural and
theoretical studies
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Moreno-Fuquen, Rodolfo' .
;
Department of Chemistry
Universidad del Valle
AA 25360
Santiago de Cali
Colombia
;
    'Arango-Daraviña, Kevin' .
;
Department of Chemistry
Universidad del Valle
AA 25360
Santiago de Cali
Colombia
;
    'Becerra, Diana' .
;
Grupo de Catálisis
Escuela de Ciencias Químicas
Universidad Pedagógica y Tecnológica de Colombia
UPTC
Avenida Central del Norte
Tunja
Colombia
;
    'Castillo, Juan-Carlos' .
;
Grupo de Catálisis
Escuela de Ciencias Químicas
Universidad Pedagógica y Tecnológica de Colombia
UPTC
Avenida Central del Norte
Tunja
Colombia
Bioorganic Compounds Research Group
Department of Chemistry
Universidad de los Andes
Carrera 1 No. 18A-10
Bogotá
Colombia
;
    'Kennedy, Alan R.' .
;
WestCHEM
Department of Pure and Applied Chemistry
University of Strathclyde
295 Cathedral Street
Glasgow G1 1XL
Scotland
;
    'Macías, Mario A.' .
;
Department of Chemistry
Universidad de los Andes
Cra. 1 N 18-A-12
111711 Bogotá
Colombia
;
_publ_section_synopsis
;\
A catalyst- and solvent-free approach for the regioselective synthesis of
2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide
through a microwave-assisted Fries rearrangement of
(5-amino-3-methylsulfanyl-1H-1,2,4-triazol-1-yl)(2-fluorophenyl)\
methanone is provided. The structures of the synthesized amides, tautomerism
and mechanistic pathway were determined by X-ray structural and theoretical
studies.
;
