##############################################################################
###                                                                        ###
###        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.                                        #
#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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/  #
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data_global
_audit_creation_method     'SHELXL-97'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2009-04-02
_journal_date_accepted     2009-04-21
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     o1116
_journal_page_last     o1116
_journal_paper_category     QO
_journal_coeditor_code     ZL2192
_publ_contact_author_name     'Dr. Wen Lirong'
_publ_contact_author_address
;
College of Chemical and Molecular Technology
Qingdao University of Science and Technology
Qingdao
Zhengzhou road No 53, Qingdao
China
;
_publ_contact_author_email     wenlirong@qust.edu.cn
_publ_contact_author_fax     '86 532 840 239 27'
_publ_contact_author_phone     '86 532 840 229 90'
_publ_section_title
;\
7-(2,4-Dichlorophenyl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine-3-\
carbonitrile
;
loop_
    _publ_author_name
    _publ_author_address
    'Li-rong Wen'
;
College of Chemistry and Molecular Engineering,
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
    'Huai-yuan Xie'
;
College of Chemistry and Molecular Engineering,
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
    'Shu-wen Wang'
;
College of Chemistry and Molecular Engineering,
Qingdao University of Science and Technology,
Qingdao 266042,
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
7-(2,4-Dichlorophenyl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine-
3-carbonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H8 Cl2 N4 S'
_chemical_formula_sum     'C14 H8 Cl2 N4 S'
_chemical_formula_iupac     'C14 H8 Cl2 N4 S'
_chemical_formula_weight     335.20
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.230(2)
_cell_length_b     14.656(4)
_cell_length_c     12.667(4)
_cell_angle_alpha     90.00
_cell_angle_beta     108.460(5)
_cell_angle_gamma     90.00
_cell_volume     1449.3(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     970
_cell_measurement_theta_min     2.78
_cell_measurement_theta_max     26.28
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.26
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.536
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     680
_exptl_absorpt_coefficient_mu     0.589
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.814
_exptl_absorpt_correction_T_max     0.879
_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     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8252
_diffrn_reflns_av_R_equivalents     0.0324
_diffrn_reflns_av_sigmaI/netI     0.0389
_diffrn_reflns_theta_min     2.62
_diffrn_reflns_theta_max     26.42
_diffrn_reflns_theta_full     26.42
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -16
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     14
_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 >
σ(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     2965
_reflns_number_gt     2181
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0679
_refine_ls_R_factor_gt     0.0431
_refine_ls_wR_factor_gt     0.0861
_refine_ls_wR_factor_ref     0.0951
_refine_ls_goodness_of_fit_ref     1.044
_refine_ls_restrained_S_all     1.044
_refine_ls_number_reflns     2965
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0395P)²+0.5056P] 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     0.216
_refine_diff_density_min     -0.291
_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'
    '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, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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
    S S1 0.07522(9) 1.04589(4) 0.33961(6) 0.0515(2) Uani d . 1 . .
    Cl Cl1 0.27654(9) 0.56767(4) 0.47097(6) 0.0587(2) Uani d . 1 . .
    Cl Cl2 0.81796(7) 0.72025(5) 0.77238(6) 0.0570(2) Uani d . 1 . .
    N N1 0.1176(2) 0.88388(12) 0.44665(15) 0.0337(4) Uani d . 1 . .
    N N2 0.0148(2) 0.81205(12) 0.45471(14) 0.0304(4) Uani d . 1 . .
    N N4 -0.4254(3) 0.99138(17) 0.2170(2) 0.0694(8) Uani d . 1 . .
    C C1 0.3585(3) 0.65420(15) 0.56647(18) 0.0351(5) Uani d . 1 . .
    C C2 0.5304(3) 0.65097(16) 0.62770(19) 0.0399(6) Uani d . 1 . .
    H H2 0.5982 0.6025 0.6193 0.048 Uiso calc R 1 . .
    C C3 0.6000(3) 0.72040(16) 0.70121(19) 0.0373(5) Uani d . 1 . .
    C C4 0.4996(3) 0.79158(16) 0.71666(19) 0.0385(5) Uani d . 1 . .
    H H4 0.5468 0.8373 0.7681 0.046 Uiso calc R 1 . .
    C C5 0.3289(3) 0.79383(16) 0.65490(19) 0.0383(5) Uani d . 1 . .
    H H5 0.2616 0.8420 0.6648 0.046 Uiso calc R 1 . .
    C C6 0.2541(3) 0.72596(14) 0.57789(18) 0.0317(5) Uani d . 1 . .
    C C7 0.0708(3) 0.73292(15) 0.51216(18) 0.0335(5) Uani d . 1 . .
    C C8 -0.0531(3) 0.66876(16) 0.5045(2) 0.0437(6) Uani d . 1 . .
    H H8 -0.0243 0.6132 0.5411 0.052 Uiso calc R 1 . .
    C C9 -0.2230(3) 0.68669(18) 0.4416(2) 0.0479(6) Uani d . 1 . .
    H H9 -0.3036 0.6412 0.4376 0.057 Uiso calc R 1 . .
    N N3 -0.2771(2) 0.76324(14) 0.38782(17) 0.0427(5) Uani d . 1 . .
    C C10 -0.1555(3) 0.82588(15) 0.39444(18) 0.0336(5) Uani d . 1 . .
    C C11 -0.1611(3) 0.91130(15) 0.34518(18) 0.0352(5) Uani d . 1 . .
    C C12 0.0087(3) 0.94280(15) 0.38006(18) 0.0342(5) Uani d . 1 . .
    C C13 0.3024(4) 1.0381(2) 0.4068(3) 0.0697(9) Uani d . 1 . .
    H H13A 0.3249 1.0229 0.4838 0.105 Uiso calc R 1 . .
    H H13B 0.3547 1.0957 0.4012 0.105 Uiso calc R 1 . .
    H H13C 0.3489 0.9916 0.3714 0.105 Uiso calc R 1 . .
    C C14 -0.3084(3) 0.95536(16) 0.2741(2) 0.0429(6) Uani d . 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
    S1 0.0594(4) 0.0374(4) 0.0588(4) 0.0004(3) 0.0206(3) 0.0114(3)
    Cl1 0.0602(4) 0.0408(4) 0.0615(4) 0.0086(3) -0.0002(3) -0.0164(3)
    Cl2 0.0290(3) 0.0678(5) 0.0654(5) 0.0002(3) 0.0025(3) 0.0056(4)
    N1 0.0313(10) 0.0320(10) 0.0379(11) 0.0008(8) 0.0110(8) 0.0017(8)
    N2 0.0266(9) 0.0312(10) 0.0319(10) 0.0020(7) 0.0069(7) 0.0012(8)
    N4 0.0641(15) 0.0544(15) 0.0648(16) 0.0238(12) -0.0150(13) -0.0040(12)
    C1 0.0396(13) 0.0294(11) 0.0335(12) 0.0021(10) 0.0075(10) 0.0003(10)
    C2 0.0361(13) 0.0379(13) 0.0445(14) 0.0101(10) 0.0113(11) 0.0052(11)
    C3 0.0276(11) 0.0421(13) 0.0400(13) -0.0003(10) 0.0075(10) 0.0083(11)
    C4 0.0385(13) 0.0377(13) 0.0347(12) -0.0040(10) 0.0049(10) -0.0013(10)
    C5 0.0391(13) 0.0346(13) 0.0388(13) 0.0072(10) 0.0089(10) -0.0002(10)
    C6 0.0309(11) 0.0302(11) 0.0312(11) 0.0028(9) 0.0056(9) 0.0034(9)
    C7 0.0338(12) 0.0325(12) 0.0323(12) 0.0048(9) 0.0079(10) 0.0029(9)
    C8 0.0417(14) 0.0374(14) 0.0475(15) -0.0015(11) 0.0075(11) 0.0110(11)
    C9 0.0385(14) 0.0461(15) 0.0550(16) -0.0102(11) 0.0089(12) 0.0053(12)
    N3 0.0289(10) 0.0456(12) 0.0497(12) -0.0016(9) 0.0070(9) 0.0027(10)
    C10 0.0280(11) 0.0383(13) 0.0327(12) 0.0045(10) 0.0069(9) -0.0005(10)
    C11 0.0353(12) 0.0347(12) 0.0319(12) 0.0072(10) 0.0054(9) 0.0002(10)
    C12 0.0391(12) 0.0320(12) 0.0319(12) 0.0021(10) 0.0117(10) 0.0001(10)
    C13 0.0535(17) 0.0595(19) 0.104(3) -0.0107(14) 0.0367(17) 0.0076(18)
    C14 0.0450(14) 0.0362(13) 0.0393(13) 0.0077(11) 0.0016(11) -0.0040(11)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    S1 C12 . 1.739(2) ?
    S1 C13 . 1.796(3) ?
    Cl1 C1 . 1.735(2) ?
    Cl2 C3 . 1.734(2) ?
    N1 C12 . 1.335(3) ?
    N1 N2 . 1.375(2) ?
    N2 C7 . 1.369(3) ?
    N2 C10 . 1.383(3) ?
    N4 C14 . 1.135(3) ?
    C1 C2 . 1.382(3) ?
    C1 C6 . 1.394(3) ?
    C2 C3 . 1.376(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.383(3) ?
    C4 C5 . 1.375(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.393(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.478(3) ?
    C7 C8 . 1.368(3) ?
    C8 C9 . 1.398(3) ?
    C8 H8 . 0.9300 ?
    C9 N3 . 1.315(3) ?
    C9 H9 . 0.9300 ?
    N3 C10 . 1.341(3) ?
    C10 C11 . 1.393(3) ?
    C11 C12 . 1.404(3) ?
    C11 C14 . 1.416(3) ?
    C13 H13A . 0.9600 ?
    C13 H13B . 0.9600 ?
    C13 H13C . 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
    C12 S1 C13 . . 100.53(12) ?
    C12 N1 N2 . . 103.65(17) ?
    C7 N2 N1 . . 125.20(17) ?
    C7 N2 C10 . . 121.97(18) ?
    N1 N2 C10 . . 112.79(17) ?
    C2 C1 C6 . . 121.5(2) ?
    C2 C1 Cl1 . . 117.98(17) ?
    C6 C1 Cl1 . . 120.48(17) ?
    C3 C2 C1 . . 119.2(2) ?
    C3 C2 H2 . . 120.4 ?
    C1 C2 H2 . . 120.4 ?
    C2 C3 C4 . . 120.9(2) ?
    C2 C3 Cl2 . . 119.44(18) ?
    C4 C3 Cl2 . . 119.59(18) ?
    C5 C4 C3 . . 119.1(2) ?
    C5 C4 H4 . . 120.4 ?
    C3 C4 H4 . . 120.4 ?
    C4 C5 C6 . . 121.8(2) ?
    C4 C5 H5 . . 119.1 ?
    C6 C5 H5 . . 119.1 ?
    C5 C6 C1 . . 117.5(2) ?
    C5 C6 C7 . . 119.43(19) ?
    C1 C6 C7 . . 123.12(19) ?
    C8 C7 N2 . . 115.24(19) ?
    C8 C7 C6 . . 126.7(2) ?
    N2 C7 C6 . . 118.02(18) ?
    C7 C8 C9 . . 120.0(2) ?
    C7 C8 H8 . . 120.0 ?
    C9 C8 H8 . . 120.0 ?
    N3 C9 C8 . . 124.7(2) ?
    N3 C9 H9 . . 117.6 ?
    C8 C9 H9 . . 117.6 ?
    C9 N3 C10 . . 115.34(19) ?
    N3 C10 N2 . . 122.7(2) ?
    N3 C10 C11 . . 132.0(2) ?
    N2 C10 C11 . . 105.25(18) ?
    C10 C11 C12 . . 105.43(18) ?
    C10 C11 C14 . . 126.5(2) ?
    C12 C11 C14 . . 128.1(2) ?
    N1 C12 C11 . . 112.9(2) ?
    N1 C12 S1 . . 122.49(17) ?
    C11 C12 S1 . . 124.61(17) ?
    S1 C13 H13A . . 109.5 ?
    S1 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    S1 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    N4 C14 C11 . . 179.3(3) ?
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
    C12 N1 N2 C7 . . . . 177.7(2) ?
    C12 N1 N2 C10 . . . . -0.1(2) ?
    C6 C1 C2 C3 . . . . -0.3(3) ?
    Cl1 C1 C2 C3 . . . . 177.75(18) ?
    C1 C2 C3 C4 . . . . 1.8(4) ?
    C1 C2 C3 Cl2 . . . . -176.31(18) ?
    C2 C3 C4 C5 . . . . -1.9(4) ?
    Cl2 C3 C4 C5 . . . . 176.16(18) ?
    C3 C4 C5 C6 . . . . 0.6(4) ?
    C4 C5 C6 C1 . . . . 0.9(3) ?
    C4 C5 C6 C7 . . . . -178.7(2) ?
    C2 C1 C6 C5 . . . . -1.0(3) ?
    Cl1 C1 C6 C5 . . . . -179.02(18) ?
    C2 C1 C6 C7 . . . . 178.6(2) ?
    Cl1 C1 C6 C7 . . . . 0.6(3) ?
    N1 N2 C7 C8 . . . . -177.0(2) ?
    C10 N2 C7 C8 . . . . 0.7(3) ?
    N1 N2 C7 C6 . . . . 4.8(3) ?
    C10 N2 C7 C6 . . . . -177.55(19) ?
    C5 C6 C7 C8 . . . . -125.1(3) ?
    C1 C6 C7 C8 . . . . 55.3(3) ?
    C5 C6 C7 N2 . . . . 52.9(3) ?
    C1 C6 C7 N2 . . . . -126.7(2) ?
    N2 C7 C8 C9 . . . . -0.3(3) ?
    C6 C7 C8 C9 . . . . 177.8(2) ?
    C7 C8 C9 N3 . . . . -0.8(4) ?
    C8 C9 N3 C10 . . . . 1.3(4) ?
    C9 N3 C10 N2 . . . . -0.9(3) ?
    C9 N3 C10 C11 . . . . 176.2(2) ?
    C7 N2 C10 N3 . . . . -0.1(3) ?
    N1 N2 C10 N3 . . . . 177.8(2) ?
    C7 N2 C10 C11 . . . . -177.85(19) ?
    N1 N2 C10 C11 . . . . 0.1(2) ?
    N3 C10 C11 C12 . . . . -177.4(2) ?
    N2 C10 C11 C12 . . . . 0.0(2) ?
    N3 C10 C11 C14 . . . . 1.9(4) ?
    N2 C10 C11 C14 . . . . 179.4(2) ?
    N2 N1 C12 C11 . . . . 0.1(2) ?
    N2 N1 C12 S1 . . . . -178.37(15) ?
    C10 C11 C12 N1 . . . . -0.1(3) ?
    C14 C11 C12 N1 . . . . -179.5(2) ?
    C10 C11 C12 S1 . . . . 178.38(17) ?
    C14 C11 C12 S1 . . . . -1.0(3) ?
    C13 S1 C12 N1 . . . . 1.7(2) ?
    C13 S1 C12 C11 . . . . -176.7(2) ?
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
    _geom_hbond_publ_flag
    C8 H8 N4 4_676 0.93 2.61 3.474(3) 154.2 yes
