tert-Butyl Hydroperoxide (TBHP)-Initiated Vicinal Sulfonamination of Alkynes: A Radical Annulation toward 3-Sulfonylindoles.
Chen, Fei; Meng, Qiang; Han, Shang-Qing; Han, Bing; Organic letters 18 (2016) 3330–3333; doi:10.1021/acs.orglett.6b01427

data_1543527
_publ_section_title
;
 tert-Butyl Hydroperoxide (TBHP)-Initiated Vicinal Sulfonamination of
 Alkynes: A Radical Annulation toward 3-Sulfonylindoles.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3330
_journal_page_last               3333
_journal_paper_doi               10.1021/acs.orglett.6b01427
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C20 H15 N O2 S'
_chemical_formula_sum            'C20 H15 N O2 S'
_chemical_formula_weight         333.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-04-27
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7582(3)
_cell_length_b                   15.1305(5)
_cell_length_c                   20.2832(7)
_cell_measurement_reflns_used    2645
_cell_measurement_temperature    294.59(10)
_cell_measurement_theta_max      28.1610
_cell_measurement_theta_min      3.7850
_cell_volume                     3301.64(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.59(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -13.00   16.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8979  -91.0000  152.0000 29

  2 omega  -45.00   55.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8979  -19.0000 -150.0000 100

  3 omega  -46.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8979  -57.0000 -180.0000 65

  4 omega   52.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       20.8979  178.0000  150.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0396322000
_diffrn_orient_matrix_UB_12      0.0027278000
_diffrn_orient_matrix_UB_13      -0.0278614000
_diffrn_orient_matrix_UB_21      -0.0348973000
_diffrn_orient_matrix_UB_22      -0.0336725000
_diffrn_orient_matrix_UB_23      -0.0157849000
_diffrn_orient_matrix_UB_31      -0.0394773000
_diffrn_orient_matrix_UB_32      0.0325260000
_diffrn_orient_matrix_UB_33      -0.0140195000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12374
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.44
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3239
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0493P)^2^+0.9378P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1240
_reflns_number_gt                2402
_reflns_number_total             3239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b01427_si_002.cif
_cod_data_source_block           chenfei_0419
_cod_depositor_comments          'Adding full bibliography for 1543527.cif.'
_cod_original_cell_volume        3301.66(19)
_cod_database_code               1543527
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
;
_olex2_date_sample_data_collection 2016-04-22
_olex2_submission_special_instructions 'No special instructions were received'