Sulfonylation of Five-Membered Heterocycles via an SNAr Reaction
Shuai Liang; Ruo-Yi Zhang; Long-Yi Xi; Shan-Yong Chen; Xiao-Qi Yu; Journal of Organic Chemistry 78 (2013) 11874–11880; doi:10.1021/jo401828b

data_4028787
_publ_section_title
;
 Sulfonylation of Five-Membered Heterocycles via an SNAr Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11874
_journal_page_last               11880
_journal_paper_doi               10.1021/jo401828b
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C9 H7 N O2 S2'
_chemical_formula_sum            'C8 H7 N2 O2 S2'
_chemical_formula_weight         227.28
_chemical_name_systematic
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 ?
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_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
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Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
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SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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_computing_structure_solution
'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.8787
_diffrn_measurement_details
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  1 omega   -3.00   23.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3611  -99.0000  150.0000 26

  2 omega   12.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0799   57.0000    0.0000 57

  3 omega   -1.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       19.0799   57.0000  -90.0000 72
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_diffrn_orient_matrix_UB_31      -0.0044987000
_diffrn_orient_matrix_UB_32      -0.0067040000
_diffrn_orient_matrix_UB_33      0.0920250000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.973
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_diffrn_reflns_limit_l_min       -9
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_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.168
_diffrn_source                   'Enhance (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.511
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_exptl_absorpt_correction_T_min  0.94343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
empirical absorption correction using spherical harmonics,
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_exptl_crystal_colour
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_exptl_crystal_density_diffrn    1.525
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_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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;
 w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+0.6979P]
 where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
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_reflns_number_gt                1302
_reflns_number_total             1740
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           130927_s3_ls
_cod_original_cell_volume        1979.65(19)
_cod_database_code               4028787
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c3h4n2o2s1
_shelx_estimated_absorpt_t_max   0.941
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_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9)
;
_shelx_res_checksum              38449