Cu-Catalyzed Direct C7-Sulfonylation of Indolines with Arylsulfonyl Chlorides.
Zhi, Changlei; Wang, Qiuling; Liu, Shuang; Xue, Yuting; Shi, Linlin; Zhu, Xinju; Hao, Xin-Qi; Song, Mao-Ping; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02954

data_4037727
_publ_section_title
;
 Cu-Catalyzed Direct C7-Sulfonylation of Indolines with Arylsulfonyl
 Chlorides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02954
_journal_year                    2019
_chemical_formula_moiety         'C19 H17 N3 O2 S'
_chemical_formula_sum            'C19 H17 N3 O2 S'
_chemical_formula_weight         351.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-12-13
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3930(4)
_cell_length_b                   7.2772(2)
_cell_length_c                   16.8277(5)
_cell_measurement_reflns_used    2704
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8950
_cell_measurement_theta_min      4.7950
_cell_volume                     1683.51(9)
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega -103.00   -4.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -78.0000 -167.0000 99

  2 omega  -49.00   37.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -150.0000 86

  3 omega   60.00  109.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -120.0000 49

  4 omega   59.00   95.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 36

  5 omega   20.00   70.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 50

  6 omega    1.00  100.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000  120.0000 99

  7 omega   70.00   96.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 26

  8 omega   37.00   72.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 35

  9 omega   94.00  176.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  150.0000 82

 10 omega  122.00  173.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 51

 11 omega   37.00   70.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 33

 12 omega   47.00   91.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 44

 13 omega   40.00   69.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 29

 14 omega   47.00  107.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 60

 15 omega   49.00   74.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 25

 16 omega   51.00   99.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 48

 17 omega   70.00   99.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 29

 18 omega  107.00  159.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  120.0000 52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0969510000
_diffrn_orient_matrix_UB_12      -0.0098498000
_diffrn_orient_matrix_UB_13      -0.0211539000
_diffrn_orient_matrix_UB_21      -0.0492368000
_diffrn_orient_matrix_UB_22      -0.1163057000
_diffrn_orient_matrix_UB_23      -0.0775522000
_diffrn_orient_matrix_UB_31      -0.0269951000
_diffrn_orient_matrix_UB_32      0.1766675000
_diffrn_orient_matrix_UB_33      -0.0521807000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6233
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.558
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.857
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25146
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.1779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2537
_reflns_number_total             3002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02954_si_002.cif
_cod_data_source_block           201812485
_cod_original_cell_volume        1683.50(9)
_cod_database_code               4037727
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N3S1
_shelx_estimated_absorpt_t_max   0.836
_shelx_estimated_absorpt_t_min   0.781
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'