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_4037726
_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 H14 N4 O2 S'
_chemical_formula_sum            'C19 H14 N4 O2 S'
_chemical_formula_weight         362.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                111.608(7)
_cell_angle_beta                 93.223(6)
_cell_angle_gamma                100.174(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3315(4)
_cell_length_b                   10.8147(8)
_cell_length_c                   11.6977(9)
_cell_measurement_reflns_used    2879
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9660
_cell_measurement_theta_min      4.1020
_cell_volume                     841.26(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00  90.00   93
  2  \w   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00   0.00   93
  3  \w   -108.00 -32.00   1.00    1.00    --  -33.50 178.00   0.00   76
  4  \w    -34.00  59.00   1.00    1.00    --   36.47 -37.00 -60.00   93
  5  \w     57.00 110.00   1.00    1.00    --   36.47 178.00 150.00   53
  6  \w    -36.00  74.00   1.00    1.00    --   36.47 -19.00-120.00  110
  7  \w     -4.00  77.00   1.00    1.00    --   36.47 -99.00 150.00   81
  8  \w     33.00  77.00   1.00    1.00    --   36.47 -99.00   0.00   44
  9  \w     78.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   32
 10  \w    -33.00  57.00   1.00    1.00    --   36.47 -37.00-180.00   90
 11  \w     -2.00  73.00   1.00    1.00    --   36.47 -99.00 -30.00   75
 12  \w     83.00 108.00   1.00    1.00    --   36.47 178.00 -30.00   25
 13  \w     38.00 110.00   1.00    1.00    --  108.00-111.00 -60.00   72
 14  \w     42.00 126.00   1.00    1.00    --  108.00 -45.00 -30.00   84
 15  \w     64.00 124.00   1.00    1.00    --  108.00 -61.00-120.00   60
 16  \w     69.00 105.00   1.00    1.00    --  108.00 -94.00  60.00   36
 17  \w     65.00 124.00   1.00    1.00    --  108.00 -45.00  30.00   59
 18  \w     71.00  98.00   1.00    1.00    --  108.00 -61.00 150.00   27
 19  \w     54.00 112.00   1.00    1.00    --  108.00-111.00-180.00   58
 20  \w     93.00 176.00   1.00    1.00    --  108.00  45.00  60.00   83
 21  \w    104.00 130.00   1.00    1.00    --  108.00 -30.00-120.00   26
 22  \w     41.00  92.00   1.00    1.00    --  108.00 -30.00-120.00   51
 23  \w     38.00 126.00   1.00    1.00    --  108.00 -45.00 120.00   88
 24  \w     52.00  87.00   1.00    1.00    --  108.00 -94.00  30.00   35
 25  \w     37.00 175.00   1.00    1.00    --  108.00   0.00  30.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1118482000
_diffrn_orient_matrix_UB_12      0.0783695000
_diffrn_orient_matrix_UB_13      0.1301403000
_diffrn_orient_matrix_UB_21      -0.0289524000
_diffrn_orient_matrix_UB_22      -0.1324864000
_diffrn_orient_matrix_UB_23      0.0240460000
_diffrn_orient_matrix_UB_31      0.1817350000
_diffrn_orient_matrix_UB_32      -0.0298438000
_diffrn_orient_matrix_UB_33      -0.0538583000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5800
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.082
_diffrn_reflns_theta_max         67.082
_diffrn_reflns_theta_min         4.101
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0100(10)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0742P)^2^+0.1324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2596
_reflns_number_total             2983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02954_si_003.cif
_cod_data_source_block           201909212
_cod_database_code               4037726
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c20h20n4o4S1
_shelx_estimated_absorpt_t_max   0.833
_shelx_estimated_absorpt_t_min   0.790
_reflns_odcompleteness_completeness 99.67
_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
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
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)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.088
_oxdiff_exptl_absorpt_empirical_full_min 0.912