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_2240995
_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          'C12 H14 N4 O2 S'
_chemical_formula_moiety         'C12 H14 N4 O2 S'
_chemical_formula_sum            'C12 H14 N4 O2 S'
_chemical_formula_weight         278.33
_chemical_name_systematic
4-[(<i>E</i>)-(3,4-Dimethoxybenzylidene)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           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   7.3112(4)
_cell_length_b                   16.0793(9)
_cell_length_c                   22.8994(13)
_cell_measurement_reflns_used    3343
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.296
_cell_measurement_theta_min      3.096
_cell_volume                     2692.0(3)
_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 0.998
_diffrn_measured_fraction_theta_max 0.999
_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  0.0646
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.096
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.237
_refine_ls_extinction_coef       0.0037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0565
_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^)+(0.0344P)^2^+3.4410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                2319
_reflns_number_total             3090
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7466sup1.cif
_cod_data_source_block           II
_cod_database_code               2240995
_cod_database_fobs_code          2240995
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.974
_shelx_hkl_checksum              51236
_shelx_res_checksum              812
_shelxl_version_number           2.014