Catalyst- and solvent-free synthesis of 2-fluoro-<i>N</i>-(3-methylsulfanyl-1<i>H</i>-1,2,4-triazol-5-yl)benzamide through a microwave-assisted Fries rearrangement: X-ray structural and theoretical studies
Moreno-Fuquen, Rodolfo; Arango-Daraviña, Kevin; Becerra, Diana; Castillo, Juan-Carlos; Kennedy, Alan R.; Macías, Mario A.; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S2053229619002572

data_2021526
_publ_section_title
;
 Catalyst- and solvent-free synthesis of
 2-fluoro-<i>N</i>-(3-methylsulfanyl-1<i>H</i>-1,2,4-triazol-5-yl)benzamide
 through a microwave-assisted Fries rearrangement: X-ray structural and
 theoretical studies
;
_journal_coeditor_code           YO3062
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229619002572
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C10 H9 F N4 O S'
_chemical_formula_moiety         'C10 H9 F N4 O S'
_chemical_formula_sum            'C10 H9 F N4 O S'
_chemical_formula_weight         252.27
_chemical_name_systematic
;
2-Fluoro-<i>N</i>-(3-methylsulfanyl-1<i>H</i>-1,2,4-triazol-5-yl)benzamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.12(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0509(11)
_cell_length_b                   26.640(5)
_cell_length_c                   8.0251(16)
_cell_measurement_reflns_used    3138
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.7370
_cell_measurement_theta_min      3.9540
_cell_volume                     1077.0(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3072
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
;
Agilent SuperNova Dual Source diffractometer with an Atlas detector
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.080
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5060
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.770
_diffrn_reflns_theta_min         3.059
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.053
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         5060
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1329P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.2371
_reflns_number_gt                3267
_reflns_number_total             5060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            yo3062sup1.cif
_cod_data_source_block           Compound_4
_cod_database_code               2021526
_cod_database_fobs_code          2021526
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.984
_shelx_hkl_checksum              67896
_shelx_res_checksum              25207