##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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.                                        #
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# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2007-11-23
_journal_date_accepted     2007-11-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      1
_journal_page_first     o45
_journal_page_last     o45
_journal_paper_category     QO
_journal_coeditor_code     HK2399
_publ_contact_author_name     'Qiong Chen'
_publ_contact_author_address
;
Key Laboratory of Pesticides and Chemical Biology of the Ministry of
Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
_publ_contact_author_email     qchen@mail.ccnu.edu.cn
_publ_contact_author_fax     '86 27 67867706'
_publ_contact_author_phone     '86 27 67867141'
_publ_section_title
;\
Ethyl
5-chloromethyl-2-methylsulfanyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-\
a]pyrimidine-6-carboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Dan-Dan Song' .
; College of Chemistry
  Central China Normal University
  Wuhan 430079
  People's Republic of China
;
    'Qiong Chen' .
; Key Laboratory of Pesticides and Chemical Biology of the Ministry of
 Education,
  College of Chemistry,
  Central China Normal University,
  Wuhan 430079
  People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Ethyl 5-chloromethyl-2-methylsulfanyl-7-phenyl-4,7-dihydro-
1,2,4-triazolo[1,5-a]pyrimidine-6-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H17 Cl N4 O2 S'
_chemical_formula_sum     'C16 H17 Cl N4 O2 S'
_chemical_formula_iupac     'C16 H17 Cl N4 O2 S'
_chemical_formula_weight     364.85
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.9280(8)
_cell_length_b     9.8217(9)
_cell_length_c     11.3775(10)
_cell_angle_alpha     106.022(2)
_cell_angle_beta     102.631(2)
_cell_angle_gamma     109.919(2)
_cell_volume     845.85(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1660
_cell_measurement_theta_min     2.39
_cell_measurement_theta_max     22.49
_cell_measurement_temperature     292(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.433
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     380
_exptl_absorpt_coefficient_mu     0.366
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     292(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 SMART 4K CCD area-detector diffractometer'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6662
_diffrn_reflns_av_R_equivalents     0.0297
_diffrn_reflns_av_sigmaI/netI     0.0495
_diffrn_reflns_theta_min     2.39
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     0.990
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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     3281
_reflns_number_gt     2295
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0813
_refine_ls_R_factor_gt     0.0553
_refine_ls_wR_factor_gt     0.1423
_refine_ls_wR_factor_ref     0.1555
_refine_ls_goodness_of_fit_ref     1.020
_refine_ls_restrained_S_all     1.020
_refine_ls_number_reflns     3281
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'calc w=1/[σ²(Fo²)+(0.0839P)²P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.396
_refine_diff_density_min     -0.418
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL (Bruker, 2001)'
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
    Cl Cl1 0.52275(12) 0.20019(13) 0.21023(8) 0.0802(4) Uani d . 1 . .
    S S1 0.33719(10) 0.12878(9) 0.82617(8) 0.0506(3) Uani d . 1 . .
    O O1 0.7924(2) 0.7426(2) 0.57614(18) 0.0458(5) Uani d . 1 . .
    O O2 0.8859(3) 0.6249(3) 0.4314(2) 0.0745(8) Uani d . 1 . .
    N N1 0.5299(3) 0.3688(3) 0.7737(2) 0.0399(6) Uani d . 1 . .
    N N2 0.4832(3) 0.1259(2) 0.6417(2) 0.0394(6) Uani d . 1 . .
    N N3 0.6027(3) 0.3760(2) 0.6786(2) 0.0378(5) Uani d . 1 . .
    N N4 0.6300(3) 0.2107(3) 0.5023(2) 0.0423(6) Uani d . 1 . .
    H H4 0.603(4) 0.119(4) 0.448(3) 0.051 Uiso d . 1 . .
    C C1 0.3128(5) 0.2917(4) 0.9220(4) 0.0875(14) Uani d . 1 . .
    H H1A 0.4175 0.3619 0.9926 0.131 Uiso calc R 1 . .
    H H1B 0.2245 0.2552 0.9564 0.131 Uiso calc R 1 . .
    H H1C 0.2831 0.3456 0.8687 0.131 Uiso calc R 1 . .
    C C2 0.4589(3) 0.2173(3) 0.7451(3) 0.0372(6) Uani d . 1 . .
    C C3 0.5739(3) 0.2331(3) 0.6044(2) 0.0355(6) Uani d . 1 . .
    C C4 0.6994(3) 0.3357(3) 0.4670(3) 0.0396(7) Uani d . 1 . .
    C C5 0.7350(3) 0.4840(3) 0.5433(3) 0.0373(6) Uani d . 1 . .
    C C6 0.7104(3) 0.5239(3) 0.6746(3) 0.0371(6) Uani d . 1 . .
    H H6 0.6505 0.5913 0.6795 0.045 Uiso calc R 1 . .
    C C7 0.7226(4) 0.2871(3) 0.3381(3) 0.0480(8) Uani d . 1 . .
    H H7A 0.7719 0.2125 0.3329 0.058 Uiso calc R 1 . .
    H H7B 0.7995 0.3778 0.3290 0.058 Uiso calc R 1 . .
    C C8 0.8112(4) 0.6191(3) 0.5077(3) 0.0434(7) Uani d . 1 . .
    C C9 0.8778(4) 0.8879(3) 0.5616(3) 0.0488(8) Uani d . 1 . .
    H H9A 0.8284 0.8785 0.4733 0.059 Uiso calc R 1 . .
    H H9B 0.9972 0.9124 0.5791 0.059 Uiso calc R 1 . .
    C C10 0.8580(4) 1.0149(4) 0.6559(3) 0.0606(9) Uani d . 1 . .
    H H10A 0.7394 0.9875 0.6405 0.091 Uiso calc R 1 . .
    H H10B 0.9090 1.1114 0.6446 0.091 Uiso calc R 1 . .
    H H10C 0.9127 1.0274 0.7433 0.091 Uiso calc R 1 . .
    C C11 0.8775(3) 0.6081(3) 0.7886(3) 0.0361(6) Uani d . 1 . .
    C C12 0.9729(4) 0.5313(4) 0.8217(3) 0.0583(9) Uani d . 1 . .
    H H12 0.9337 0.4245 0.7752 0.070 Uiso calc R 1 . .
    C C13 1.1272(5) 0.6119(5) 0.9238(4) 0.0715(11) Uani d . 1 . .
    H H13 1.1902 0.5587 0.9461 0.086 Uiso calc R 1 . .
    C C14 1.1866(4) 0.7682(5) 0.9914(3) 0.0668(10) Uani d . 1 . .
    H H14 1.2904 0.8218 1.0595 0.080 Uiso calc R 1 . .
    C C15 1.0946(4) 0.8466(4) 0.9596(3) 0.0609(9) Uani d . 1 . .
    H H15 1.1353 0.9536 1.0058 0.073 Uiso calc R 1 . .
    C C16 0.9403(4) 0.7662(3) 0.8584(3) 0.0489(8) Uani d . 1 . .
    H H16 0.8778 0.8202 0.8371 0.059 Uiso calc R 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
    N1 N3 . 1.385(3) ?
    N4 H4 . 0.85(3) ?
    C1 S1 . 1.782(4) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 N1 . 1.312(3) ?
    C2 N2 . 1.378(3) ?
    C2 S1 . 1.740(3) ?
    C3 N3 . 1.324(3) ?
    C3 N2 . 1.326(3) ?
    C3 N4 . 1.356(3) ?
    C4 C5 . 1.357(4) ?
    C4 N4 . 1.384(3) ?
    C4 C7 . 1.495(4) ?
    C5 C8 . 1.480(4) ?
    C5 C6 . 1.521(4) ?
    C6 N3 . 1.463(3) ?
    C6 C11 . 1.521(4) ?
    C6 H6 . 0.9800 ?
    C7 Cl1 . 1.780(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 O2 . 1.207(3) ?
    C8 O1 . 1.334(3) ?
    C9 O1 . 1.446(3) ?
    C9 C10 . 1.494(4) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 C16 . 1.374(4) ?
    C11 C12 . 1.376(4) ?
    C12 C13 . 1.387(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.358(5) ?
    C13 H13 . 0.9300 ?
    C14 C15 . 1.361(5) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.382(4) ?
    C15 H15 . 0.9300 ?
    C16 H16 . 0.9300 ?
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 S1 C1 . . 99.99(15) ?
    C8 O1 C9 . . 116.3(2) ?
    C2 N1 N3 . . 101.5(2) ?
    C3 N2 C2 . . 101.5(2) ?
    C3 N3 N1 . . 109.8(2) ?
    C3 N3 C6 . . 127.0(2) ?
    N1 N3 C6 . . 122.9(2) ?
    C3 N4 C4 . . 119.2(2) ?
    C3 N4 H4 . . 121(2) ?
    C4 N4 H4 . . 118(2) ?
    S1 C1 H1A . . 109.5 ?
    S1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    S1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    N1 C2 N2 . . 115.8(2) ?
    N1 C2 S1 . . 124.5(2) ?
    N2 C2 S1 . . 119.64(19) ?
    N3 C3 N2 . . 111.5(2) ?
    N3 C3 N4 . . 120.3(2) ?
    N2 C3 N4 . . 128.2(2) ?
    C5 C4 N4 . . 121.2(2) ?
    C5 C4 C7 . . 125.8(3) ?
    N4 C4 C7 . . 113.0(2) ?
    C4 C5 C8 . . 121.9(2) ?
    C4 C5 C6 . . 122.5(2) ?
    C8 C5 C6 . . 115.5(2) ?
    N3 C6 C11 . . 111.1(2) ?
    N3 C6 C5 . . 106.7(2) ?
    C11 C6 C5 . . 112.6(2) ?
    N3 C6 H6 . . 108.8 ?
    C11 C6 H6 . . 108.8 ?
    C5 C6 H6 . . 108.8 ?
    C4 C7 Cl1 . . 109.7(2) ?
    C4 C7 H7A . . 109.7 ?
    Cl1 C7 H7A . . 109.7 ?
    C4 C7 H7B . . 109.7 ?
    Cl1 C7 H7B . . 109.7 ?
    H7A C7 H7B . . 108.2 ?
    O2 C8 O1 . . 122.2(3) ?
    O2 C8 C5 . . 127.1(3) ?
    O1 C8 C5 . . 110.6(2) ?
    O1 C9 C10 . . 108.3(2) ?
    O1 C9 H9A . . 110.0 ?
    C10 C9 H9A . . 110.0 ?
    O1 C9 H9B . . 110.0 ?
    C10 C9 H9B . . 110.0 ?
    H9A C9 H9B . . 108.4 ?
    C9 C10 H10A . . 109.5 ?
    C9 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    C9 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C16 C11 C12 . . 118.2(3) ?
    C16 C11 C6 . . 120.1(3) ?
    C12 C11 C6 . . 121.7(2) ?
    C11 C12 C13 . . 120.5(3) ?
    C11 C12 H12 . . 119.8 ?
    C13 C12 H12 . . 119.8 ?
    C14 C13 C12 . . 120.3(3) ?
    C14 C13 H13 . . 119.9 ?
    C12 C13 H13 . . 119.9 ?
    C13 C14 C15 . . 120.2(3) ?
    C13 C14 H14 . . 119.9 ?
    C15 C14 H14 . . 119.9 ?
    C14 C15 C16 . . 119.7(3) ?
    C14 C15 H15 . . 120.2 ?
    C16 C15 H15 . . 120.2 ?
    C11 C16 C15 . . 121.3(3) ?
    C11 C16 H16 . . 119.4 ?
    C15 C16 H16 . . 119.4 ?
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
    N4 C4 C5 C8 . . . . 179.2(3) ?
    C7 C4 C5 C8 . . . . -3.1(4) ?
    N4 C4 C5 C6 . . . . 3.4(4) ?
    C7 C4 C5 C6 . . . . -179.0(3) ?
    C4 C5 C6 N3 . . . . -15.7(4) ?
    C8 C5 C6 N3 . . . . 168.2(2) ?
    C4 C5 C6 C11 . . . . 106.4(3) ?
    C8 C5 C6 C11 . . . . -69.7(3) ?
    C5 C4 C7 Cl1 . . . . -102.2(3) ?
    N4 C4 C7 Cl1 . . . . 75.7(3) ?
    C4 C5 C8 O2 . . . . -18.9(5) ?
    C6 C5 C8 O2 . . . . 157.3(3) ?
    C4 C5 C8 O1 . . . . 163.3(3) ?
    C6 C5 C8 O1 . . . . -20.5(3) ?
    N3 C6 C11 C16 . . . . -135.1(3) ?
    C5 C6 C11 C16 . . . . 105.3(3) ?
    N3 C6 C11 C12 . . . . 47.4(4) ?
    C5 C6 C11 C12 . . . . -72.2(3) ?
    C16 C11 C12 C13 . . . . 0.7(5) ?
    C6 C11 C12 C13 . . . . 178.2(3) ?
    C11 C12 C13 C14 . . . . -0.7(6) ?
    C12 C13 C14 C15 . . . . 0.4(6) ?
    C13 C14 C15 C16 . . . . 0.0(6) ?
    C12 C11 C16 C15 . . . . -0.3(5) ?
    C6 C11 C16 C15 . . . . -177.8(3) ?
    C14 C15 C16 C11 . . . . -0.1(5) ?
    N2 C2 N1 N3 . . . . 1.7(3) ?
    S1 C2 N1 N3 . . . . -177.30(19) ?
    N3 C3 N2 C2 . . . . 0.4(3) ?
    N4 C3 N2 C2 . . . . -177.2(3) ?
    N1 C2 N2 C3 . . . . -1.3(3) ?
    S1 C2 N2 C3 . . . . 177.67(19) ?
    N2 C3 N3 N1 . . . . 0.6(3) ?
    N4 C3 N3 N1 . . . . 178.4(2) ?
    N2 C3 N3 C6 . . . . 174.0(2) ?
    N4 C3 N3 C6 . . . . -8.2(4) ?
    C2 N1 N3 C3 . . . . -1.3(3) ?
    C2 N1 N3 C6 . . . . -175.0(2) ?
    C11 C6 N3 C3 . . . . -104.4(3) ?
    C5 C6 N3 C3 . . . . 18.7(4) ?
    C11 C6 N3 N1 . . . . 68.2(3) ?
    C5 C6 N3 N1 . . . . -168.8(2) ?
    N3 C3 N4 C4 . . . . -7.7(4) ?
    N2 C3 N4 C4 . . . . 169.7(3) ?
    C5 C4 N4 C3 . . . . 9.7(4) ?
    C7 C4 N4 C3 . . . . -168.2(2) ?
    O2 C8 O1 C9 . . . . -4.6(4) ?
    C5 C8 O1 C9 . . . . 173.3(2) ?
    C10 C9 O1 C8 . . . . -173.8(2) ?
    N1 C2 S1 C1 . . . . 10.4(3) ?
    N2 C2 S1 C1 . . . . -168.5(3) ?
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
    N4 H4 N2 2_656 0.85(3) 2.11(3) 2.939(3) 164(3)
    C7 H7B O2 . 0.97 2.15 2.888(4) 132.0
