##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1496665'
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2016-07-20
_journal_date_accepted     2016-07-29
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      8
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616012293
_journal_coeditor_code     TK4020
_publ_contact_author_name     'Youness El Bakri'
_publ_contact_author_address
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de compétences Pharmacochimie, Mohammed V University in Rabat,
BP 1014 Avenue Ibn Batouta, Rabat
Morocco
;
_publ_contact_author_email     'y_elbakri@yahoo.com'
_publ_contact_author_fax     '212 537 77 54 40'
_publ_contact_author_phone     '212 537 77 54 40'
_publ_section_title
;\
6-Methyl-7H-1,2,4-triazolo[4,3-b][1,2,4]triazepin-8(9H)-\
thione
;
loop_
    _publ_author_name
    _publ_author_address
    'El Bakri, Youness'
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat,
BP 1014 Avenue Ibn Batouta, Rabat
Morocco
;
    'Harmaoui, Abdallah'
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat,
BP 1014 Avenue Ibn Batouta, Rabat
Morocco
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique Hétérocyclique URAC 21,
Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat,
BP 1014 Avenue Ibn Batouta, Rabat
Morocco
;
    'Saadi, Mohamed'
;
Laboratoire de Chimie du Solide Appliquée,
Faculty of Sciences, Mohammed V University in Rabat
Avenue Ibn Battouta, BP 1014, Rabat,
Morocco
;
    'El Ammari, Lahcen'
;
Laboratoire de Chimie du Solide Appliquée,
Faculty of Sciences, Mohammed V University in Rabat
Avenue Ibn Battouta, BP 1014, Rabat,
Morocco
;
_publ_section_synopsis
;\
In
6-methyl-7H-1,2,4-triazolo[4,3-b][1,2,4]triazepin-8(9H)-\
thione, the triazepine ring displays a boat conformation. In the crystal,
molecules are linked into centrosymmetric dimers by N---H...N hydrogen bonds.
;
_chemical_name_systematic
;\
6-Methyl-7H-1,2,4-triazolo[4,3-b][1,2,4]triazepin-\
8(9H)-thione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H7 N5 S'
_chemical_formula_sum     'C6 H7 N5 S'
_chemical_formula_iupac     'C6 H7 N5 S'
_chemical_formula_weight     181.23
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.238(2)
_cell_length_b     7.234(3)
_cell_length_c     10.887(4)
_cell_angle_alpha     103.331(15)
_cell_angle_beta     92.329(16)
_cell_angle_gamma     113.846(15)
_cell_volume     432.3(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2287
_cell_measurement_theta_min     3.198
_cell_measurement_theta_max     29.563
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.26
_exptl_crystal_density_diffrn     1.392
_exptl_crystal_F_000     188
_exptl_absorpt_coefficient_mu     0.325
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_min     0.6444
_exptl_absorpt_correction_T_max     0.7467
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker X8 APEX'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     10195
_diffrn_reflns_av_R_equivalents     0.0324
_diffrn_reflns_theta_min     3.198
_diffrn_reflns_theta_max     29.563
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.943
_diffrn_measured_fraction_theta_full     0.951
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     15
_reflns_number_total     2287
_reflns_number_gt     2038
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0443
_refine_ls_R_factor_gt     0.0394
_refine_ls_wR_factor_gt     0.1145
_refine_ls_wR_factor_ref     0.1194
_refine_ls_goodness_of_fit_ref     1.073
_refine_ls_restrained_S_all     1.073
_refine_ls_number_reflns     2287
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0613P)²+0.1769P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.469
_refine_diff_density_min     -0.376
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'S' 'S' 0.1246 0.1234
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia,
2012)
;
_computing_publication_material
;
Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.5444(3) 0.3425(2) 0.76025(13) 0.0284(3) Uani d 1 . .
    C C2 0.3456(3) 0.4034(2) 0.79409(13) 0.0306(3) Uani d 1 . .
    H H2A 0.1951 0.2807 0.7656 0.037 Uiso calc 1 . .
    H H2B 0.3627 0.4553 0.8861 0.037 Uiso calc 1 . .
    C C3 0.3466(3) 0.5699(2) 0.73291(14) 0.0318(3) Uani d 1 . .
    C C4 0.4105(4) 0.7857(3) 0.81648(19) 0.0507(5) Uani d 1 . .
    H H4A 0.5692 0.8425 0.8607 0.076 Uiso calc 1 . .
    H H4B 0.3025 0.7790 0.8775 0.076 Uiso calc 1 . .
    H H4C 0.4007 0.8741 0.7650 0.076 Uiso calc 1 . .
    C C5 0.1097(3) 0.2566(2) 0.41943(15) 0.0344(3) Uani d 1 . .
    H H5 0.0219 0.3170 0.3869 0.041 Uiso calc 1 . .
    C C6 0.3465(2) 0.2043(2) 0.54244(13) 0.0253(3) Uani d 1 . .
    N N1 0.2954(2) 0.54000(18) 0.61292(13) 0.0324(3) Uani d 1 . .
    N N2 0.2479(2) 0.33992(17) 0.53619(11) 0.0275(2) Uani d 1 . .
    N N3 0.1165(2) 0.0823(2) 0.35948(12) 0.0345(3) Uani d 1 . .
    N N4 0.2688(2) 0.04725(18) 0.43825(11) 0.0295(3) Uani d 1 . .
    N N5 0.5193(2) 0.23657(19) 0.63695(11) 0.0290(3) Uani d 1 . .
    H H5N 0.6036 0.1688 0.6148 0.035 Uiso d 1 . .
    S S1 0.77311(8) 0.39546(8) 0.86328(4) 0.04839(17) Uani d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N5 . 1.3509(18) ?
    C1 C2 . 1.5072(19) ?
    C1 S1 . 1.6343(16) ?
    C2 C3 . 1.503(2) ?
    C2 H2A . 0.9700 ?
    C2 H2B . 0.9700 ?
    C3 N1 . 1.279(2) ?
    C3 C4 . 1.495(2) ?
    C4 H4A . 0.9600 ?
    C4 H4B . 0.9600 ?
    C4 H4C . 0.9600 ?
    C5 N3 . 1.298(2) ?
    C5 N2 . 1.3636(19) ?
    C5 H5 . 0.9300 ?
    C6 N4 . 1.3144(17) ?
    C6 N2 . 1.3647(17) ?
    C6 N5 . 1.3675(18) ?
    N1 N2 . 1.3986(16) ?
    N3 N4 . 1.3898(18) ?
    N5 H5N . 0.8599 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N5 C1 C2 . . 114.93(12) ?
    N5 C1 S1 . . 121.53(11) ?
    C2 C1 S1 . . 123.54(10) ?
    C3 C2 C1 . . 111.00(12) ?
    C3 C2 H2A . . 109.4 ?
    C1 C2 H2A . . 109.4 ?
    C3 C2 H2B . . 109.4 ?
    C1 C2 H2B . . 109.4 ?
    H2A C2 H2B . . 108.0 ?
    N1 C3 C4 . . 117.00(15) ?
    N1 C3 C2 . . 124.37(12) ?
    C4 C3 C2 . . 118.62(15) ?
    C3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    C3 C4 H4C . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    N3 C5 N2 . . 111.33(13) ?
    N3 C5 H5 . . 124.3 ?
    N2 C5 H5 . . 124.3 ?
    N4 C6 N2 . . 110.24(12) ?
    N4 C6 N5 . . 124.33(12) ?
    N2 C6 N5 . . 125.12(12) ?
    C3 N1 N2 . . 115.92(12) ?
    C5 N2 C6 . . 104.35(11) ?
    C5 N2 N1 . . 122.64(12) ?
    C6 N2 N1 . . 132.08(12) ?
    C5 N3 N4 . . 106.88(12) ?
    C6 N4 N3 . . 107.19(12) ?
    C1 N5 C6 . . 125.05(12) ?
    C1 N5 H5N . . 120.1 ?
    C6 N5 H5N . . 114.4 ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N5 H5N N4 2_656 0.86 2.01 2.8530(18) 167
    C2 H2A N3 2_556 0.97 2.56 3.487(2) 161
    C5 H5 N1 2_566 0.93 2.58 3.442(2) 155
