Synthesis and crystal structure of 3-(adamantan-1-yl)-4-(2-bromo-4-fluorophenyl)-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
Abdelrazeq, Alaa S.; Ghabbour, Hazem A.; El-Emam, Ali A.; Osman, Doaa Ahmed; Garcia-Granda, Santiago; Acta Crystallographica Section E 76 (2020) 162–166; doi:10.1107/S2056989020000092

data_2243242
_publ_section_title
;
 Synthesis and crystal structure of
 3-(adamantan-1-yl)-4-(2-bromo-4-fluorophenyl)-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
;
_journal_coeditor_code           XI2020
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              162
_journal_page_last               166
_journal_paper_doi               10.1107/S2056989020000092
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C18 H19 Br F N3 S'
_chemical_formula_moiety         'C18 H19 Br F N3 S'
_chemical_formula_sum            'C18 H19 Br F N3 S'
_chemical_formula_weight         408.32
_chemical_name_systematic
3-(Adamantan-1-yl)-4-(2-bromo-4-fluorophenyl)-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.84730(10)
_cell_length_b                   12.5587(2)
_cell_length_c                   19.8090(3)
_cell_measurement_reflns_used    5537
_cell_measurement_temperature    150.6(9)
_cell_measurement_theta_max      74.5840
_cell_measurement_theta_min      4.1520
_cell_volume                     1703.44(4)
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012), Mercury (Macrae <i>et al.</i>,
2008),
SCHAKAL (Keller, 1989), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
WINGX (Farrugia, 2012), PARST (Nardelli, 1995), publCIF
(Westrip, 2010),
enCIFer (Allen <i>et al.</i>,  2004) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015)
;
_computing_structure_solution
;
<i>SIR2011</i> (Burla <i>et al.</i>,  2012)
;
_diffrn_ambient_temperature      150.6(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2673
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent Excalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13191
_diffrn_reflns_theta_full        67.5
_diffrn_reflns_theta_max         76.25
_diffrn_reflns_theta_min         4.17
_exptl_absorpt_coefficient_mu    4.56
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Agilent 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.356
_refine_ls_abs_structure_details
;
Flack (1983)
;
_refine_ls_abs_structure_Flack   0.50(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+1.0546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0812
_reflns_number_gt                3244
_reflns_number_total             3572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xi2020sup1.cif
_cod_data_source_block           I
_cod_database_code               2243242
_cod_database_fobs_code          2243242