The crystal structures of three 3-methyl-1<i>H</i>-1,2,4-triazole-5-thiones, including a second polymorph of 4-[(<i>E</i>)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione and a redetermination of 4-amino-3-methyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
Manjula, Padmanabha S.; Sarojini, Balladka K.; Yathirajan, Hemmige S.; Akkurt, Mehmet; Ersanlı, Cem Cüneyt; Glidewell, Christopher; Acta Crystallographica Section E 71 (2015) 1003–1009; doi:10.1107/S205698901501422X

data_2240996
_publ_section_title
;
 The crystal structures of three
 3-methyl-1<i>H</i>-1,2,4-triazole-5-thiones, including a second polymorph
 of
 4-[(<i>E</i>)-(5-bromo-2-hydroxybenzylidene)amino]-3-methyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
 and a redetermination of
 4-amino-3-methyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
;
_journal_coeditor_code           HB7466
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1003
_journal_page_last               1009
_journal_paper_doi               10.1107/S205698901501422X
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C10 H9 Br N4 O S'
_chemical_formula_moiety         'C10 H9 Br N4 O S'
_chemical_formula_sum            'C10 H9 Br N4 O S'
_chemical_formula_weight         313.17
_chemical_name_systematic
4-[(<i>E</i>)-(5-Bromo-2-hydroxybenzylidene)amino]-3-methyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL2014
_cell_angle_alpha                90
_cell_angle_beta                 95.828(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4122(4)
_cell_length_b                   14.7450(13)
_cell_length_c                   18.7911(16)
_cell_measurement_reflns_used    3002
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.311
_cell_measurement_theta_min      3.520
_cell_volume                     1216.19(19)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22155
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.548
_diffrn_reflns_theta_min         3.520
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.540
_exptl_absorpt_correction_T_max  0.588
_exptl_absorpt_correction_T_min  0.376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.574
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.273
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.273
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+5.4069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                1913
_reflns_number_total             2270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7466sup1.cif
_cod_data_source_block           III
_cod_database_code               2240996
_cod_database_fobs_code          2240996
_shelx_estimated_absorpt_t_min   0.510
_shelx_estimated_absorpt_t_max   0.619
_shelx_hkl_checksum              5024
_shelx_res_checksum              80788
_shelxl_version_number           2.014