Tosyl cyanide as a C-sulfinylating agent: 3-sulfinylation of 4-hydroxycoumarins and related heterocycles
Akula, Ramulu; Ibrahim, Hasim; RSC Advances 3 (2013) 25719–; doi:10.1039/c3ra45987j

data_7239418
_publ_section_title
;
 Tosyl cyanide as a C-sulfinylating agent: 3-sulfinylation of
 4-hydroxycoumarins and related heterocycles
;
_journal_issue                   48
_journal_name_full               'RSC Advances'
_journal_page_first              25719
_journal_paper_doi               10.1039/c3ra45987j
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C17 H14 O4 S'
_chemical_formula_sum            'C17 H14 O4 S'
_chemical_formula_weight         314.34
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.959(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.2101(6)
_cell_length_b                   7.1147(2)
_cell_length_c                   15.2952(7)
_cell_measurement_reflns_used    13566
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8776
_cell_measurement_theta_min      3.4278
_cell_volume                     1401.94(11)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Aug  2 2010,13:00:58) 
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Aug  2 2010,13:00:58) 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Aug  2 2010,13:00:58) 
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16011
_diffrn_reflns_theta_full        77.01
_diffrn_reflns_theta_max         77.01
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    2.204
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Aug  2 2010,13:00:58) 
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.1946
_exptl_crystal_size_mid          0.1512
_exptl_crystal_size_min          0.0507
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0467P)^2^+0.6866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0824
_reflns_number_gt                2765
_reflns_number_total             2820
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c3ra45987j.txt
_cod_data_source_block           c:\data\has27\rechnung\has27
_cod_original_cell_volume        1401.94(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7239418