##############################################################################
###                                                                        ###
###        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/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_journal_date_recd_electronic     2005-09-27
_journal_date_accepted     2005-10-18
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     11
_journal_page_first     o3852
_journal_page_last     o3854
_journal_paper_category     EO
_journal_coeditor_code     AC6208
_publ_contact_author
;
      Dr Viktor Kettmann
      Faculty of Pharmacy
      Comenius University
      Odbojarov 10
      Bratislava   83232
      Slovak Republic
;
_publ_contact_author_email     kettmann@fpharm.uniba.sk
_publ_contact_author_phone     '00421250117254'
_publ_section_title
;
5-Amino-4-methylsulfonyl-1-phenyl-1H-pyrazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Viktor Kettmann '
;
Faculty of Pharmacy
Comenius University
Odbojarov 10
Bratislava 83232
Slovak Republic
;
    'Jan Lokaj'
;
Faculty of Food and Chemical Technology
Slovak Technical University
Radlinskeho 9
Bratislava 81237
Slovak Republic
;
    'Viktor Milata'
;
Faculty of Food and Chemical Technology
Slovak Technical University
Radlinskeho 9
Bratislava 81237
Slovak Republic
;
    "Petra C̆ernuchová"
;
Faculty of Food and Chemical Technology
Slovak Technical University
Radlinskeho 9
Bratislava 81237
Slovak Republic
;
    "André Loupy"
;
Laboratory of Selective Reactions on Supports
ICMMO, CNRS UMR 8615, Building 410
Paris-South University
Orsay Cedex 91405
France
;
    'Giang Vo-Thanh'
;
Laboratory of Selective Reactions on Supports
ICMMO, CNRS UMR 8615, Building 410
Paris-South University
Orsay Cedex 91405
France
;
data_I
_chemical_name_systematic
;
5-Amino-4-methylsulfonyl-1-phenyl-1H-pyrazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H11 N3 O2 S'
_chemical_formula_sum     'C10 H11 N3 O2 S'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C10 H11 N3 O2 S'
_chemical_formula_weight     237.28
_chemical_melting_point     407
_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     8.083(2)
_cell_length_b     12.274(3)
_cell_length_c     11.040(3)
_cell_angle_alpha     90.00
_cell_angle_beta     95.20(3)
_cell_angle_gamma     90.00
_cell_volume     1090.8(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     20
_cell_measurement_theta_min     7
_cell_measurement_theta_max     20
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.445
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu     0.285
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_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 P4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3298
_diffrn_reflns_av_R_equivalents     0.0386
_diffrn_reflns_av_sigmaI/netI     0.0378
_diffrn_reflns_theta_min     2.49
_diffrn_reflns_theta_max     27.49
_diffrn_reflns_theta_full     27.49
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -1
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -1
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     3
_diffrn_standards_interval_count     97
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     2
_reflns_number_total     2504
_reflns_number_gt     2080
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0488
_refine_ls_R_factor_gt     0.0383
_refine_ls_wR_factor_gt     0.0992
_refine_ls_wR_factor_ref     0.1055
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     2504
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w = 1/[σ²(Fo²)+(0.051P)²+0.3P] 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_diff_density_max     0.251
_refine_diff_density_min     -0.268
_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     'XSCANS (Siemens, 1991)'
_computing_cell_refinement     'XSCANS'
_computing_data_reduction     'XSCANS'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLUTON92 (Spek, 1992)'
_computing_publication_material     'SHELXL97'
loop_
    _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
    _atom_site_type_symbol
    N1 0.58298(17) 0.67943(12) 0.44428(12) 0.0327(3) Uani d . 1 . . N
    N2 0.60842(18) 0.70948(13) 0.56571(13) 0.0393(3) Uani d . 1 . . N
    C3 0.4813(2) 0.77146(15) 0.58330(15) 0.0375(4) Uani d . 1 . . C
    H3 0.4640 0.8029 0.6578 0.045 Uiso calc R 1 . . H
    C4 0.37345(19) 0.78532(13) 0.47696(14) 0.0309(3) Uani d . 1 . . C
    C5 0.44344(19) 0.72442(13) 0.38750(14) 0.0293(3) Uani d . 1 . . C
    C6 0.6987(2) 0.60653(14) 0.39555(14) 0.0332(3) Uani d . 1 . . C
    C7 0.8652(2) 0.63415(15) 0.40759(17) 0.0412(4) Uani d . 1 . . C
    H7 0.9000 0.6995 0.4442 0.049 Uiso calc R 1 . . H
    C8 0.9792(3) 0.56350(18) 0.3646(2) 0.0515(5) Uani d . 1 . . C
    H8 1.0916 0.5811 0.3723 0.062 Uiso calc R 1 . . H
    C9 0.9269(3) 0.46736(18) 0.3106(2) 0.0559(5) Uani d . 1 . . C
    H9 1.0041 0.4199 0.2819 0.067 Uiso calc R 1 . . H
    C10 0.7608(3) 0.44073(17) 0.2984(2) 0.0559(5) Uani d . 1 . . C
    H10 0.7268 0.3756 0.2610 0.067 Uiso calc R 1 . . H
    C11 0.6437(2) 0.50997(16) 0.34145(18) 0.0455(4) Uani d . 1 . . C
    H11 0.5315 0.4919 0.3341 0.055 Uiso calc R 1 . . H
    S1 0.19650(5) 0.86328(3) 0.46018(4) 0.03279(14) Uani d . 1 . . S
    O1 0.11200(17) 0.83895(13) 0.34374(12) 0.0520(4) Uani d . 1 . . O
    O2 0.10668(17) 0.85023(12) 0.56575(12) 0.0494(4) Uani d . 1 . . O
    C12 0.2621(3) 1.00009(16) 0.4589(2) 0.0505(5) Uani d . 1 . . C
    H12A 0.3241 1.0122 0.3900 0.076 Uiso calc R 1 . . H
    H12B 0.3311 1.0155 0.5323 0.076 Uiso calc R 1 . . H
    H12C 0.1668 1.0471 0.4537 0.076 Uiso calc R 1 . . H
    N3 0.39312(18) 0.70690(13) 0.26915(13) 0.0404(4) Uani d . 1 . . N
    H3A 0.4504 0.6655 0.2260 0.048 Uiso calc R 1 . . H
    H3B 0.3038 0.7371 0.2369 0.048 Uiso calc R 1 . . H
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 0.0318(7) 0.0383(7) 0.0277(6) 0.0024(6) 0.0012(5) -0.0022(6)
    N2 0.0397(8) 0.0494(9) 0.0278(7) 0.0026(7) -0.0029(6) -0.0029(6)
    C3 0.0407(9) 0.0444(9) 0.0273(8) 0.0005(7) 0.0020(6) -0.0047(7)
    C4 0.0303(8) 0.0353(8) 0.0275(7) -0.0013(6) 0.0038(6) -0.0018(6)
    C5 0.0280(7) 0.0322(8) 0.0279(7) -0.0035(6) 0.0029(5) 0.0008(6)
    C6 0.0349(8) 0.0335(8) 0.0311(8) 0.0033(6) 0.0030(6) 0.0029(6)
    C7 0.0377(9) 0.0427(9) 0.0434(9) -0.0010(8) 0.0049(7) 0.0025(8)
    C8 0.0398(10) 0.0601(13) 0.0561(12) 0.0114(9) 0.0127(8) 0.0119(10)
    C9 0.0664(14) 0.0496(11) 0.0546(12) 0.0221(10) 0.0212(10) 0.0071(10)
    C10 0.0733(15) 0.0378(10) 0.0577(12) 0.0075(10) 0.0123(11) -0.0065(9)
    C11 0.0463(10) 0.0393(10) 0.0509(11) -0.0003(8) 0.0042(8) -0.0036(8)
    S1 0.0264(2) 0.0411(2) 0.0316(2) -0.00034(16) 0.00733(14) -0.00084(16)
    O1 0.0391(7) 0.0732(10) 0.0421(7) 0.0080(7) -0.0054(6) -0.0076(7)
    O2 0.0426(7) 0.0634(9) 0.0455(8) 0.0007(6) 0.0223(6) 0.0021(6)
    C12 0.0449(11) 0.0391(10) 0.0690(14) 0.0039(8) 0.0143(9) 0.0054(9)
    N3 0.0385(8) 0.0544(9) 0.0276(7) 0.0108(7) -0.0009(5) -0.0067(6)
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 C5 . 1.357(2) yes
    N1 N2 . 1.388(2) yes
    N1 C6 . 1.434(2) yes
    N2 C3 . 1.307(2) yes
    C3 C4 . 1.408(2) yes
    C3 H3 . 0.9300 ?
    C4 C5 . 1.398(2) yes
    C4 S1 . 1.717(2) yes
    C5 N3 . 1.350(2) yes
    C6 C7 . 1.383(2) ?
    C6 C11 . 1.382(3) ?
    C7 C8 . 1.380(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.372(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.376(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.388(3) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    S1 O1 . 1.4314(14) yes
    S1 O2 . 1.4368(14) yes
    S1 C12 . 1.761(2) ?
    C12 H12A . 0.9600 ?
    C12 H12B . 0.9600 ?
    C12 H12C . 0.9600 ?
    N3 H3A . 0.8600 ?
    N3 H3B . 0.8600 ?
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
    C5 N1 N2 . . 112.47(13) yes
    C5 N1 C6 . . 128.59(14) yes
    N2 N1 C6 . . 118.93(13) yes
    C3 N2 N1 . . 104.39(13) yes
    N2 C3 C4 . . 112.46(15) yes
    N2 C3 H3 . . 123.8 ?
    C4 C3 H3 . . 123.8 ?
    C5 C4 C3 . . 105.36(14) yes
    C5 C4 S1 . . 127.45(12) yes
    C3 C4 S1 . . 127.17(13) yes
    N3 C5 N1 . . 123.17(15) yes
    N3 C5 C4 . . 131.53(15) yes
    N1 C5 C4 . . 105.29(14) ?
    C7 C6 C11 . . 121.60(17) ?
    C7 C6 N1 . . 118.25(16) ?
    C11 C6 N1 . . 120.11(16) ?
    C8 C7 C6 . . 119.16(18) ?
    C8 C7 H7 . . 120.4 ?
    C6 C7 H7 . . 120.4 ?
    C9 C8 C7 . . 120.1(2) ?
    C9 C8 H8 . . 120.0 ?
    C7 C8 H8 . . 120.0 ?
    C8 C9 C10 . . 120.41(19) ?
    C8 C9 H9 . . 119.8 ?
    C10 C9 H9 . . 119.8 ?
    C9 C10 C11 . . 120.7(2) ?
    C9 C10 H10 . . 119.6 ?
    C11 C10 H10 . . 119.6 ?
    C6 C11 C10 . . 118.04(19) ?
    C6 C11 H11 . . 121.0 ?
    C10 C11 H11 . . 121.0 ?
    O1 S1 O2 . . 118.04(9) yes
    O1 S1 C4 . . 107.80(8) yes
    O2 S1 C4 . . 109.12(8) yes
    O1 S1 C12 . . 108.13(11) ?
    O2 S1 C12 . . 106.70(10) ?
    C4 S1 C12 . . 106.48(9) ?
    S1 C12 H12A . . 109.5 ?
    S1 C12 H12B . . 109.5 ?
    H12A C12 H12B . . 109.5 ?
    S1 C12 H12C . . 109.5 ?
    H12A C12 H12C . . 109.5 ?
    H12B C12 H12C . . 109.5 ?
    C5 N3 H3A . . 120.0 ?
    C5 N3 H3B . . 120.0 ?
    H3A N3 H3B . . 120.0 ?
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
    C5 N1 N2 C3 . . . . 1.27(19) ?
    C6 N1 N2 C3 . . . . -177.58(15) ?
    N1 N2 C3 C4 . . . . -1.1(2) ?
    N2 C3 C4 C5 . . . . 0.6(2) ?
    N2 C3 C4 S1 . . . . -177.98(13) ?
    N2 N1 C5 N3 . . . . -179.98(15) ?
    C6 N1 C5 N3 . . . . -1.3(3) ?
    N2 N1 C5 C4 . . . . -0.94(18) ?
    C6 N1 C5 C4 . . . . 177.78(16) ?
    C3 C4 C5 N3 . . . . 179.18(18) ?
    S1 C4 C5 N3 . . . . -2.3(3) ?
    C3 C4 C5 N1 . . . . 0.25(18) ?
    S1 C4 C5 N1 . . . . 178.78(12) ?
    C5 N1 C6 C7 . . . . 126.59(18) ?
    N2 N1 C6 C7 . . . . -54.8(2) yes
    C5 N1 C6 C11 . . . . -55.3(2) ?
    N2 N1 C6 C11 . . . . 123.36(18) ?
    C11 C6 C7 C8 . . . . -0.1(3) ?
    N1 C6 C7 C8 . . . . 178.04(16) ?
    C6 C7 C8 C9 . . . . 0.1(3) ?
    C7 C8 C9 C10 . . . . 0.2(3) ?
    C8 C9 C10 C11 . . . . -0.6(3) ?
    C7 C6 C11 C10 . . . . -0.3(3) ?
    N1 C6 C11 C10 . . . . -178.36(17) ?
    C9 C10 C11 C6 . . . . 0.6(3) ?
    C5 C4 S1 O1 . . . . 11.38(18) yes
    C3 C4 S1 O1 . . . . -170.40(16) ?
    C5 C4 S1 O2 . . . . 140.72(15) ?
    C3 C4 S1 O2 . . . . -41.06(18) ?
    C5 C4 S1 C12 . . . . -104.46(17) ?
    C3 C4 S1 C12 . . . . 73.77(18) ?
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
    N3 H3A O2 4_675 0.86 2.27 3.036(2) 148
    N3 H3B O1 . 0.86 2.38 2.968(2) 126
    N3 H3B N2 4_575 0.86 2.44 3.234(2) 154
