tert-Butyl Nitrite Promoted Oxidative Intermolecular Sulfonamination of Alkynes to Synthesize Substituted Sulfonyl Pyrroles from the Alkynylamines and Sulfinic Acids.
Qi, Zhenjie; Jiang, Yong; Wang, Yanyan; Yan, Rulong; The Journal of organic chemistry 83 (2018) 8636–8644; doi:10.1021/acs.joc.8b00741

data_4035616
_publ_section_title
;
 tert-Butyl Nitrite Promoted Oxidative Intermolecular Sulfonamination of
 Alkynes to Synthesize Substituted Sulfonyl Pyrroles from the
 Alkynylamines and Sulfinic Acids.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8636
_journal_page_last               8644
_journal_paper_doi               10.1021/acs.joc.8b00741
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H28 O3 S'
_chemical_formula_sum            'C21 H28 O3 S'
_chemical_formula_weight         360.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-10-31
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
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_cell_length_c                   23.0771(8)
_cell_measurement_reflns_used    2643
_cell_measurement_temperature    293.38(10)
_cell_measurement_theta_max      26.2440
_cell_measurement_theta_min      3.6580
_cell_volume                     2125.31(15)
_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)
;
_computing_data_collection
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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)
;
_computing_data_reduction
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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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.38(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega -101.00  -72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  178.0000    0.0000 29

  2 omega  -99.00  -73.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  178.0000 -120.0000 26

  3 omega  -10.00   43.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -99.0000  150.0000 53

  4 omega  -35.00   84.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   19.0000   30.0000 119
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0824142000
_diffrn_orient_matrix_UB_12      -0.0046466000
_diffrn_orient_matrix_UB_13      -0.0105598000
_diffrn_orient_matrix_UB_21      0.0144912000
_diffrn_orient_matrix_UB_22      0.0593526000
_diffrn_orient_matrix_UB_23      0.0073933000
_diffrn_orient_matrix_UB_31      0.0273675000
_diffrn_orient_matrix_UB_32      -0.0174581000
_diffrn_orient_matrix_UB_33      0.0279068000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7911
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.53
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45823
_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,
 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    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0397P)^2^+0.3789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                3435
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00741_si_003.cif
_cod_data_source_block           yanrl_1030
_cod_original_cell_volume        2125.31(14)
_cod_database_code               4035616
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C),
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_olex2_date_sample_data_collection 2017-10-31
_olex2_submission_special_instructions 'No special instructions were received'