##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-11-07
_journal_date_accepted     2007-12-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o412
_journal_page_last     o412
_journal_paper_category     QO
_journal_coeditor_code     YA2060
_publ_contact_author_name     'Dr. Sai Bi'
_publ_contact_author_address
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
_publ_contact_author_email     qustchemistry@126.com
_publ_contact_author_fax     '+86 532 84022750'
_publ_contact_author_phone     '+86 532 84022750'
_publ_section_title
;\
3,3-Dimethyl-1-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3,4-thiadiazol-2-\
ylsulfanyl]butan-2-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Qing-Li Wei' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
    'Fu-Jin He' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
    'Fang Li' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
    'Sai Bi' ?
;     College of Chemistry and Molecular Engineering
      Qingdao University of Science and Technology
      266042 Qingdao, Shandong
      People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3,3-Dimethyl-1-[5-(1H-1,2,4-triazol-1-ylmethyl)-1,3,4-thiadiazol-2-\
ylsulfanyl]butan-2-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H15 N5 O S2'
_chemical_formula_sum     'C11 H15 N5 O S2'
_chemical_formula_iupac     'C11 H15 N5 O S2'
_chemical_formula_weight     297.40
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.9723(8)
_cell_length_b     10.1103(8)
_cell_length_c     10.1734(8)
_cell_angle_alpha     60.7280(10)
_cell_angle_beta     80.3400(10)
_cell_angle_gamma     65.4160(10)
_cell_volume     731.30(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2210
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     25.6
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.41
_exptl_crystal_size_mid     0.22
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.351
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     312
_exptl_absorpt_coefficient_mu     0.364
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.865
_exptl_absorpt_correction_T_max     0.938
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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
;
Siemens SMART 1000 CCD area-detector
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     8.33
_diffrn_reflns_number     3810
_diffrn_reflns_av_R_equivalents     0.010
_diffrn_reflns_av_sigmaI/netI     0.017
_diffrn_reflns_theta_min     2.3
_diffrn_reflns_theta_max     25.0
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2529
_reflns_number_gt     2246
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.055
_refine_ls_R_factor_gt     0.050
_refine_ls_wR_factor_gt     0.138
_refine_ls_wR_factor_ref     0.143
_refine_ls_goodness_of_fit_ref     1.05
_refine_ls_restrained_S_all     1.05
_refine_ls_number_reflns     2529
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0806P)²+0.357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.51
_refine_diff_density_min     -0.38
_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'
    'O' 'O' 0.0106 0.0060
                         '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     'SMART (Siemens, 1996)'
_computing_cell_refinement     'SAINT (Siemens, 1996)'
_computing_data_reduction     'SAINT  (Siemens, 1996)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 1997)'
_computing_publication_material
;
SHELXTL (Sheldrick, 1997), PARST (Nardelli, 1995) and PLATON
(Spek, 2003)
;
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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 0.5556(3) 0.4597(3) 0.7067(3) 0.0680(7) Uani d . 1 . .
    N N2 0.6886(3) 0.4050(3) 0.7986(3) 0.0670(6) Uani d . 1 . .
    N N3 0.2627(3) 0.8466(3) 0.4764(2) 0.0546(5) Uani d . 1 . .
    N N4 0.2154(4) 0.9710(3) 0.5103(3) 0.0718(7) Uani d . 1 . .
    N N5 0.2371(4) 1.0629(3) 0.2618(3) 0.0762(7) Uani d . 1 . .
    O O1 1.0413(3) 0.4947(2) 0.7133(2) 0.0746(6) Uani d . 1 . .
    S S1 0.49906(8) 0.68646(9) 0.77341(9) 0.0627(3) Uani d . 1 . .
    S S2 0.81659(9) 0.48127(9) 0.96116(8) 0.0609(2) Uani d . 1 . .
    C C1 0.6733(3) 0.5099(3) 0.8425(3) 0.0508(6) Uani d . 1 . .
    C C2 0.4489(3) 0.6004(3) 0.6854(3) 0.0548(6) Uani d . 1 . .
    C C3 0.2921(4) 0.6795(4) 0.5949(4) 0.0698(8) Uani d . 1 . .
    H H3A 0.2954 0.6133 0.5496 0.084 Uiso calc R 1 . .
    H H3B 0.2013 0.6817 0.6618 0.084 Uiso calc R 1 . .
    C C4 0.2003(4) 1.0979(3) 0.3766(3) 0.0657(7) Uani d . 1 . .
    H H4 0.1665 1.2043 0.3630 0.079 Uiso calc R 1 . .
    C C5 0.2751(4) 0.9038(4) 0.3298(3) 0.0695(8) Uani d . 1 . .
    H H5 0.3066 0.8398 0.2807 0.083 Uiso calc R 1 . .
    C C6 0.9842(3) 0.3090(3) 0.9519(3) 0.0543(6) Uani d . 1 . .
    H H6A 1.0658 0.2611 1.0311 0.065 Uiso calc R 1 . .
    H H6B 0.9439 0.2261 0.9711 0.065 Uiso calc R 1 . .
    C C7 1.0658(3) 0.3532(3) 0.8017(3) 0.0501(6) Uani d . 1 . .
    C C8 1.1780(4) 0.2127(3) 0.7691(3) 0.0629(7) Uani d . 1 . .
    C C9 1.2994(7) 0.0845(7) 0.8962(5) 0.199(4) Uani d . 1 . .
    H H9A 1.3660 0.1311 0.9096 0.298 Uiso calc R 1 . .
    H H9B 1.3679 -0.0042 0.8744 0.298 Uiso calc R 1 . .
    H H9C 1.2430 0.0437 0.9868 0.298 Uiso calc R 1 . .
    C C10 1.2626(5) 0.2749(5) 0.6225(4) 0.0910(11) Uani d . 1 . .
    H H10A 1.3325 0.3208 0.6317 0.136 Uiso calc R 1 . .
    H H10B 1.1816 0.3581 0.5422 0.136 Uiso calc R 1 . .
    H H10C 1.3272 0.1853 0.6008 0.136 Uiso calc R 1 . .
    C C11 1.0686(7) 0.1417(8) 0.7445(8) 0.154(3) Uani d . 1 . .
    H H11A 1.1360 0.0522 0.7235 0.231 Uiso calc R 1 . .
    H H11B 0.9921 0.2261 0.6609 0.231 Uiso calc R 1 . .
    H H11C 1.0097 0.1028 0.8338 0.231 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N1 0.0740(15) 0.0541(13) 0.0763(16) -0.0174(12) -0.0189(12) -0.0300(12)
    N2 0.0678(14) 0.0555(13) 0.0776(16) -0.0112(11) -0.0206(12) -0.0341(12)
    N3 0.0551(12) 0.0475(11) 0.0590(13) -0.0186(9) -0.0090(10) -0.0209(10)
    N4 0.0947(18) 0.0605(14) 0.0618(14) -0.0268(13) 0.0001(13) -0.0315(12)
    N5 0.0926(19) 0.0611(15) 0.0560(14) -0.0159(13) -0.0140(13) -0.0200(12)
    O1 0.0788(13) 0.0500(11) 0.0763(13) -0.0282(10) 0.0123(11) -0.0161(10)
    S1 0.0575(4) 0.0554(4) 0.0780(5) -0.0157(3) -0.0043(3) -0.0359(4)
    S2 0.0656(4) 0.0655(5) 0.0606(4) -0.0234(3) -0.0027(3) -0.0359(4)
    C1 0.0536(13) 0.0487(13) 0.0494(13) -0.0200(11) 0.0021(11) -0.0222(11)
    C2 0.0572(14) 0.0470(14) 0.0568(14) -0.0238(12) -0.0020(11) -0.0175(11)
    C3 0.0673(17) 0.0545(15) 0.0793(19) -0.0301(14) -0.0174(15) -0.0138(14)
    C4 0.0773(18) 0.0486(15) 0.0634(17) -0.0160(13) -0.0089(14) -0.0239(13)
    C5 0.0795(19) 0.0606(17) 0.0645(18) -0.0124(14) -0.0127(14) -0.0336(15)
    C6 0.0585(14) 0.0493(13) 0.0493(14) -0.0200(11) -0.0091(11) -0.0161(11)
    C7 0.0472(12) 0.0462(13) 0.0537(14) -0.0198(10) -0.0097(10) -0.0162(11)
    C8 0.0658(16) 0.0536(15) 0.0588(16) -0.0192(13) 0.0017(13) -0.0216(13)
    C9 0.181(6) 0.165(5) 0.085(3) 0.104(5) -0.051(3) -0.063(3)
    C10 0.095(3) 0.095(3) 0.082(2) -0.037(2) 0.021(2) -0.046(2)
    C11 0.170(5) 0.186(5) 0.237(7) -0.129(5) 0.117(5) -0.176(6)
_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
    N1 C2 . 1.274(3) ?
    N1 N2 . 1.387(3) ?
    N2 C1 . 1.290(3) ?
    N3 C5 . 1.313(4) ?
    N3 N4 . 1.347(3) ?
    N3 C3 . 1.456(3) ?
    N4 C4 . 1.314(4) ?
    N5 C5 . 1.310(4) ?
    N5 C4 . 1.332(4) ?
    O1 C7 . 1.205(3) ?
    S1 C1 . 1.715(3) ?
    S1 C2 . 1.728(3) ?
    S2 C1 . 1.751(3) ?
    S2 C6 . 1.799(3) ?
    C2 C3 . 1.498(4) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 H4 . 0.9300 ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.516(4) ?
    C6 H6A . 0.9700 ?
    C6 H6B . 0.9700 ?
    C7 C8 . 1.517(4) ?
    C8 C9 . 1.482(5) ?
    C8 C10 . 1.515(4) ?
    C8 C11 . 1.544(5) ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
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
    C2 N1 N2 . . 113.0(2) ?
    C1 N2 N1 . . 111.5(2) ?
    C5 N3 N4 . . 109.3(2) ?
    C5 N3 C3 . . 130.1(3) ?
    N4 N3 C3 . . 120.6(2) ?
    C4 N4 N3 . . 102.1(2) ?
    C5 N5 C4 . . 102.3(2) ?
    C1 S1 C2 . . 86.46(12) ?
    C1 S2 C6 . . 98.80(12) ?
    N2 C1 S1 . . 114.8(2) ?
    N2 C1 S2 . . 124.2(2) ?
    S1 C1 S2 . . 121.01(15) ?
    N1 C2 C3 . . 121.9(3) ?
    N1 C2 S1 . . 114.2(2) ?
    C3 C2 S1 . . 123.9(2) ?
    N3 C3 C2 . . 112.9(2) ?
    N3 C3 H3A . . 109.0 ?
    C2 C3 H3A . . 109.0 ?
    N3 C3 H3B . . 109.0 ?
    C2 C3 H3B . . 109.0 ?
    H3A C3 H3B . . 107.8 ?
    N4 C4 N5 . . 115.0(3) ?
    N4 C4 H4 . . 122.5 ?
    N5 C4 H4 . . 122.5 ?
    N5 C5 N3 . . 111.1(3) ?
    N5 C5 H5 . . 124.4 ?
    N3 C5 H5 . . 124.4 ?
    C7 C6 S2 . . 113.74(17) ?
    C7 C6 H6A . . 108.8 ?
    S2 C6 H6A . . 108.8 ?
    C7 C6 H6B . . 108.8 ?
    S2 C6 H6B . . 108.8 ?
    H6A C6 H6B . . 107.7 ?
    O1 C7 C6 . . 120.5(2) ?
    O1 C7 C8 . . 122.2(2) ?
    C6 C7 C8 . . 117.3(2) ?
    C9 C8 C10 . . 111.0(4) ?
    C9 C8 C7 . . 110.6(3) ?
    C10 C8 C7 . . 110.9(2) ?
    C9 C8 C11 . . 110.8(5) ?
    C10 C8 C11 . . 106.0(3) ?
    C7 C8 C11 . . 107.3(3) ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    C8 C10 H10A . . 109.5 ?
    C8 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C8 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C8 C11 H11A . . 109.5 ?
    C8 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C8 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C2 N1 N2 C1 . . . . 0.3(4) ?
    C5 N3 N4 C4 . . . . 0.9(3) ?
    C3 N3 N4 C4 . . . . -179.3(2) ?
    N1 N2 C1 S1 . . . . -1.4(3) ?
    N1 N2 C1 S2 . . . . 179.3(2) ?
    C2 S1 C1 N2 . . . . 1.6(2) ?
    C2 S1 C1 S2 . . . . -179.13(18) ?
    C6 S2 C1 N2 . . . . 13.2(3) ?
    C6 S2 C1 S1 . . . . -166.03(16) ?
    N2 N1 C2 C3 . . . . -177.4(3) ?
    N2 N1 C2 S1 . . . . 0.9(3) ?
    C1 S1 C2 N1 . . . . -1.4(2) ?
    C1 S1 C2 C3 . . . . 176.9(2) ?
    C5 N3 C3 C2 . . . . 105.8(3) ?
    N4 N3 C3 C2 . . . . -74.1(4) ?
    N1 C2 C3 N3 . . . . -127.9(3) ?
    S1 C2 C3 N3 . . . . 53.9(4) ?
    N3 N4 C4 N5 . . . . -1.1(4) ?
    C5 N5 C4 N4 . . . . 0.9(4) ?
    C4 N5 C5 N3 . . . . -0.3(4) ?
    N4 N3 C5 N5 . . . . -0.4(4) ?
    C3 N3 C5 N5 . . . . 179.8(3) ?
    C1 S2 C6 C7 . . . . 71.9(2) ?
    S2 C6 C7 O1 . . . . 15.0(3) ?
    S2 C6 C7 C8 . . . . -165.12(19) ?
    O1 C7 C8 C9 . . . . 129.1(4) ?
    C6 C7 C8 C9 . . . . -50.8(5) ?
    O1 C7 C8 C10 . . . . 5.4(4) ?
    C6 C7 C8 C10 . . . . -174.5(2) ?
    O1 C7 C8 C11 . . . . -109.9(4) ?
    C6 C7 C8 C11 . . . . 70.2(4) ?
