True symmetry or pseudosymmetry: 5-amino-1-(4-methylphenylsulfonyl)-4-pyrazolin-3-one and a comparison with its 1-phenylsulfonyl analogue
Elgemeie, Galal H.; Sayed, Shahinaz H.; Jones, Peter G.; Acta Crystallographica Section C 69 (2013) 90–92; doi:10.1107/S0108270112049906

data_2018742
_publ_section_title
;
 True symmetry or pseudosymmetry:
 5-amino-1-(4-methylphenylsulfonyl)-4-pyrazolin-3-one and a comparison
 with its 1-phenylsulfonyl analogue
;
_journal_coeditor_code           FA3297
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              90
_journal_page_last               92
_journal_paper_doi               10.1107/S0108270112049906
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C10 H11 N3 O3 S'
_chemical_formula_moiety         'C10 H11 N3 O3 S'
_chemical_formula_sum            'C10 H11 N3 O3 S'
_chemical_formula_weight         253.28
_chemical_name_systematic
;
5-Amino-1-(4-methylphenylsulfonyl)-4-pyrazolin-3-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.778(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.9857(2)
_cell_length_b                   7.9094(2)
_cell_length_c                   11.6777(2)
_cell_measurement_reflns_used    20410
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7970
_cell_measurement_theta_min      2.3538
_cell_volume                     1104.64(4)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2011)'
_computing_data_collection       'CrysAlis PRO (Oxford Diffraction, 2011)'
_computing_data_reduction        'CrysAlis PRO (Oxford Diffraction, 2011)'
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Oxford Xcalibur Eos'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            55463
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.87
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.437
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.8152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0826
_reflns_number_gt                3081
_reflns_number_total             3349
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fa3297.cif
_cod_data_source_block           I
_cod_original_cell_volume        1104.63(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018742
_cod_database_fobs_code          2018742