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_2240994
_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          'C3 H6 N4 S'
_chemical_formula_moiety         'C3 H6 N4 S'
_chemical_formula_sum            'C3 H6 N4 S'
_chemical_formula_weight         130.18
_chemical_name_systematic
;
4-Amino-3-methyl-1<i>H</i>-1,2,4-triazole-5(4<i>H</i>)-thione
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           57
_space_group_name_Hall           '-P 2c 2b'
_space_group_name_H-M_alt        'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'
_symmetry_space_group_name_H-M   'P b c m'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8682(6)
_cell_length_b                   9.8230(6)
_cell_length_c                   6.5427(4)
_cell_measurement_reflns_used    753
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.298
_cell_measurement_theta_min      4.149
_cell_volume                     569.95(6)
_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 0.972
_diffrn_measured_fraction_theta_max 0.977
_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  0.0191
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5602
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_min         4.149
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.287
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     55
_refine_ls_number_reflns         753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0324P)^2^+0.3610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                687
_reflns_number_total             753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7466sup1.cif
_cod_data_source_block           I
_cod_database_code               2240994
_shelx_estimated_absorpt_t_min   0.899
_shelx_estimated_absorpt_t_max   0.935
_shelx_hkl_checksum              84770
_shelx_res_checksum              94604
_shelxl_version_number           2.014
_cod_database_fobs_code 2240994