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#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/85/2228522.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228522
loop_
_publ_author_name
'Mojzych, Mariusz'
'Karczmarzyk, Zbigniew'
'Wysocki, Waldemar'
_publ_section_title
;
 1,3-Dimethyl-5-methylsulfonyl-1H-pyrazolo[4,3-e][1,2,4]triazine
;
_journal_coeditor_code           PV2349
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3226
_journal_paper_doi               10.1107/S1600536810047264
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C7 H9 N5 O2 S'
_chemical_formula_moiety         'C7 H9 N5 O2 S'
_chemical_formula_sum            'C7 H9 N5 O2 S'
_chemical_formula_weight         227.25
_chemical_melting_point          444
_chemical_name_systematic
;
1,3-Dimethyl-5-methylsulfonyl-1H-pyrazolo[4,3-e][1,2,4]triazine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.9010(10)
_cell_length_b                   8.1268(7)
_cell_length_c                   14.203(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      4.43
_cell_volume                     2011.9(5)
_computing_cell_refinement
'KM4B8 (Gałdecki et al., 1996)'
_computing_data_collection
'KM4B8 (Gałdecki et al., 1996)'
_computing_data_reduction        'DATAPROC (Gałdecki et al., 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Kuma KM-4 four-circle'
_diffrn_measurement_method       'ω-2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.1960
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3688
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        1.39
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.719
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.2442
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.2267
_reflns_number_gt                1085
_reflns_number_total             2948
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2349.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2228522
_cod_database_fobs_code          2228522
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'
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_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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24784025
