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###                                                                        ###
###        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):       #
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#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
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# Software is freely available for graphical display of the structure(s) in  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1,3-Dimethyl-5-methylsulfonyl-1H-pyrazolo[4,3-e][1,2,4]triazine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H9 N5 O2 S'
_chemical_formula_sum     'C7 H9 N5 O2 S'
_chemical_formula_iupac     'C7 H9 N5 O2 S'
_chemical_formula_weight     227.25
_chemical_melting_point     '444'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     17.9010(10)
_cell_length_b     8.1268(7)
_cell_length_c     14.203(3)
_cell_angle_alpha     90.00
_cell_angle_beta     103.170(10)
_cell_angle_gamma     90.00
_cell_volume     2011.9(5)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     4.43
_cell_measurement_theta_max     25.16
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.500
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     944
_exptl_absorpt_coefficient_mu     0.311
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.860
_exptl_absorpt_correction_T_max     0.980
_exptl_special_details
;
Yield: 95% and m.p. 444 K.
¹H NMR (CDCl₃) δ: 2.77 (s, 3H), 3.57 (s,
3H), 4.39 (s, 3H);
IR (KBr,ν, cm⁻¹): 2920, 1330, 1120;
MS (m/z, %): 227(8) [M⁺], 199(32), 120(21), 95(51), 79(94),
67(28), 52(100).
Analysis calculated for C₇H₉N₅O₂S: C 37.00, H 3.99, N
30.82%; found: C 37.01, H 3.85, N 30.76%.
;
_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     'Kuma KM-4 four-circle'
_diffrn_measurement_method     'ω-2θ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3688
_diffrn_reflns_av_R_equivalents     0.0638
_diffrn_reflns_av_sigmaI/netI     0.1960
_diffrn_reflns_theta_min     2.34
_diffrn_reflns_theta_max     30.07
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -25
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -1
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     2
_diffrn_standards_interval_count     100
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     1.39
_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     2948
_reflns_number_gt     1085
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.2442
_refine_ls_R_factor_gt     0.0693
_refine_ls_wR_factor_gt     0.1746
_refine_ls_wR_factor_ref     0.2267
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_restrained_S_all     1.018
_refine_ls_number_reflns     2948
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.1000P)²] 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     0.806
_refine_diff_density_min     -0.719
_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     'KM4B8 (Gałdecki et al., 1996)'
_computing_cell_refinement     'KM4B8 (Gałdecki et al., 1996)'
_computing_data_reduction     'DATAPROC (Gałdecki et al., 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                         'SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999)'
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 S12 0.15935(7) 0.15917(15) 0.19815(10) 0.0433(4) Uani d . 1 . .
    O O13 0.1310(2) 0.0271(5) 0.1348(3) 0.0748(13) Uani d . 1 . .
    O O14 0.1737(2) 0.1313(5) 0.3001(3) 0.0765(13) Uani d . 1 . .
    N N1 0.0756(2) 0.6040(5) 0.1881(3) 0.0412(10) Uani d . 1 . .
    N N2 0.1192(2) 0.4699(5) 0.2062(3) 0.0373(9) Uani d . 1 . .
    N N4 0.02186(19) 0.2860(5) 0.1191(3) 0.0361(9) Uani d . 1 . .
    N N7 -0.0502(2) 0.6833(5) 0.0994(3) 0.0388(9) Uani d . 1 . .
    N N8 -0.1138(2) 0.6061(5) 0.0483(3) 0.0435(10) Uani d . 1 . .
    C C3 0.0915(2) 0.3259(5) 0.1696(3) 0.0317(9) Uani d . 1 . .
    C C5 -0.0227(2) 0.4200(5) 0.1003(3) 0.0336(10) Uani d . 1 . .
    C C6 0.0051(2) 0.5751(5) 0.1322(3) 0.0332(10) Uani d . 1 . .
    C C9 -0.0993(2) 0.4447(6) 0.0469(3) 0.0377(11) Uani d . 1 . .
    C C10 -0.0494(3) 0.8619(6) 0.1113(4) 0.0586(15) Uani d . 1 . .
    H H10A -0.0770 0.8909 0.1594 0.088 Uiso calc R 1 . .
    H H10B -0.0732 0.9128 0.0509 0.088 Uiso calc R 1 . .
    H H10C 0.0027 0.8995 0.1315 0.088 Uiso calc R 1 . .
    C C11 -0.1567(3) 0.3236(6) -0.0021(4) 0.0567(14) Uani d . 1 . .
    H H11A -0.2011 0.3804 -0.0381 0.085 Uiso calc R 1 . .
    H H11B -0.1712 0.2539 0.0453 0.085 Uiso calc R 1 . .
    H H11C -0.1350 0.2579 -0.0454 0.085 Uiso calc R 1 . .
    C C15 0.2416(3) 0.2357(8) 0.1689(5) 0.0646(17) Uani d . 1 . .
    H H15A 0.2807 0.1526 0.1803 0.097 Uiso calc R 1 . .
    H H15B 0.2593 0.3302 0.2083 0.097 Uiso calc R 1 . .
    H H15C 0.2303 0.2669 0.1020 0.097 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
    S12 0.0358(6) 0.0407(7) 0.0504(7) 0.0015(6) 0.0035(5) 0.0050(6)
    O13 0.058(2) 0.044(2) 0.108(3) 0.0052(19) -0.011(2) -0.022(2)
    O14 0.075(3) 0.096(3) 0.057(2) 0.030(2) 0.012(2) 0.036(2)
    N1 0.0313(19) 0.047(2) 0.042(2) -0.0005(18) 0.0021(16) -0.0085(19)
    N2 0.0316(18) 0.038(2) 0.039(2) 0.0034(17) 0.0013(15) 0.0006(18)
    N4 0.0315(18) 0.040(2) 0.035(2) -0.0049(16) 0.0025(16) 0.0024(17)
    N7 0.0339(19) 0.040(2) 0.040(2) 0.0048(18) 0.0033(16) -0.0033(18)
    N8 0.0247(18) 0.063(3) 0.041(2) 0.0028(18) 0.0028(16) 0.000(2)
    C3 0.0264(18) 0.036(2) 0.031(2) -0.0035(19) 0.0035(16) 0.001(2)
    C5 0.0250(19) 0.045(3) 0.030(2) 0.000(2) 0.0058(16) 0.003(2)
    C6 0.027(2) 0.041(3) 0.030(2) 0.0020(19) 0.0049(16) -0.006(2)
    C9 0.025(2) 0.051(3) 0.035(3) -0.004(2) 0.0017(18) 0.007(2)
    C10 0.057(3) 0.052(3) 0.061(4) 0.014(3) 0.000(3) -0.003(3)
    C11 0.036(2) 0.065(3) 0.062(3) -0.022(3) -0.005(2) 0.006(3)
    C15 0.035(3) 0.073(4) 0.089(4) 0.009(3) 0.020(3) 0.023(3)
_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
    S12 O13 . 1.418(4) ?
    S12 O14 . 1.430(4) ?
    S12 C15 . 1.733(5) ?
    S12 C3 . 1.803(4) ?
    N1 N2 . 1.331(5) ?
    N1 C6 . 1.350(5) ?
    N2 C3 . 1.330(5) ?
    N4 C3 . 1.329(5) ?
    N4 C5 . 1.340(5) ?
    N7 C6 . 1.326(5) ?
    N7 N8 . 1.357(5) ?
    N7 C10 . 1.461(6) ?
    N8 C9 . 1.338(6) ?
    C5 C6 . 1.393(6) ?
    C5 C9 . 1.423(6) ?
    C9 C11 . 1.476(6) ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 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
    O13 S12 O14 . . 118.6(3) ?
    O13 S12 C15 . . 108.7(3) ?
    O14 S12 C15 . . 109.4(3) ?
    O13 S12 C3 . . 107.5(2) ?
    O14 S12 C3 . . 107.6(2) ?
    C15 S12 C3 . . 104.0(2) ?
    N2 N1 C6 . . 113.5(4) ?
    N1 N2 C3 . . 119.7(3) ?
    C3 N4 C5 . . 110.6(4) ?
    C6 N7 N8 . . 110.5(4) ?
    C6 N7 C10 . . 129.1(4) ?
    N8 N7 C10 . . 120.4(4) ?
    C9 N8 N7 . . 108.6(3) ?
    N4 C3 N2 . . 130.3(4) ?
    N4 C3 S12 . . 116.0(3) ?
    N2 C3 S12 . . 113.6(3) ?
    N4 C5 C6 . . 121.3(4) ?
    N4 C5 C9 . . 132.7(4) ?
    C6 C5 C9 . . 106.0(4) ?
    N7 C6 N1 . . 127.9(4) ?
    N7 C6 C5 . . 107.7(4) ?
    N1 C6 C5 . . 124.4(4) ?
    N8 C9 C5 . . 107.3(4) ?
    N8 C9 C11 . . 123.0(4) ?
    C5 C9 C11 . . 129.8(4) ?
    N7 C10 H10A . . 109.5 ?
    N7 C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    N7 C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    C9 C11 H11A . . 109.5 ?
    C9 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C9 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    S12 C15 H15A . . 109.5 ?
    S12 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    S12 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 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
    C6 N1 N2 C3 . . . . 0.2(6) ?
    C6 N7 N8 C9 . . . . -0.8(5) ?
    C10 N7 N8 C9 . . . . 179.0(4) ?
    C5 N4 C3 N2 . . . . 4.2(6) ?
    C5 N4 C3 S12 . . . . -178.4(3) ?
    N1 N2 C3 N4 . . . . -4.5(7) ?
    N1 N2 C3 S12 . . . . 178.1(3) ?
    O13 S12 C3 N4 . . . . 17.9(4) ?
    O14 S12 C3 N4 . . . . -110.9(4) ?
    C15 S12 C3 N4 . . . . 133.0(4) ?
    O13 S12 C3 N2 . . . . -164.3(3) ?
    O14 S12 C3 N2 . . . . 66.9(4) ?
    C15 S12 C3 N2 . . . . -49.2(4) ?
    C3 N4 C5 C6 . . . . 0.0(6) ?
    C3 N4 C5 C9 . . . . 177.3(4) ?
    N8 N7 C6 N1 . . . . -177.9(4) ?
    C10 N7 C6 N1 . . . . 2.4(8) ?
    N8 N7 C6 C5 . . . . 1.0(5) ?
    C10 N7 C6 C5 . . . . -178.8(5) ?
    N2 N1 C6 N7 . . . . -177.7(4) ?
    N2 N1 C6 C5 . . . . 3.7(6) ?
    N4 C5 C6 N7 . . . . 177.2(4) ?
    C9 C5 C6 N7 . . . . -0.8(5) ?
    N4 C5 C6 N1 . . . . -3.9(7) ?
    C9 C5 C6 N1 . . . . 178.1(4) ?
    N7 N8 C9 C5 . . . . 0.2(5) ?
    N7 N8 C9 C11 . . . . 179.5(4) ?
    N4 C5 C9 N8 . . . . -177.3(4) ?
    C6 C5 C9 N8 . . . . 0.3(5) ?
    N4 C5 C9 C11 . . . . 3.5(8) ?
    C6 C5 C9 C11 . . . . -178.9(5) ?
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
    C10 H10C O13 1_565 0.96 2.51 3.442(7) 163 y
    C11 H11B O14 2_555 0.96 2.42 3.341(7) 161 y
    C15 H15A N2 4_545 0.96 2.59 3.466(7) 152 y
    Cg(pyrazole) . Cg(triazine) 2_555 . . 3.778(3) . n
    Cg(pyrazole) . Cg(triazine) 3_565 . . 3.416(3) . n
data_global
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-10-28
_journal_date_accepted     2010-11-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue     12
_journal_page_first     o3226
_journal_page_last     o3226
_journal_paper_category     QO
_journal_coeditor_code     PV2349
_publ_contact_author_name     'Zbigniew Karczmarzyk'
_publ_contact_author_address
;
Department of Chemistry
University of Podlasie
ul. 3 Maja 54
08-100 siedlce, Poland
;
_publ_contact_author_email     kar@uph.edu.pl
_publ_contact_author_fax     '48 25 644 20 45'
_publ_contact_author_phone     '48 25 643 10 17'
_publ_section_title
;
1,3-Dimethyl-5-methylsulfonyl-1H-pyrazolo[4,3-e][1,2,4]triazine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mojzych, Mariusz' .
;
Department of Chemistry
University of Podlasie
ul. 3 Maja 54
08-110 Siedlce, Poland
;
    'Karczmarzyk, Zbigniew' .
;
Department of Chemistry
University of Podlasie
ul. 3 Maja 54
08-110 Siedlce, Poland
;
    'Wysocki, Waldemar' .
;
Department of Chemistry
University of Podlasie
ul. 3 Maja 54
08-110 Siedlce, Poland
;
_publ_section_synopsis     .
