Pd-catalysed intramolecular transformations of indolylbenzenesulfonamides: ortho-sulfonamido-bi(hetero)aryls via C2-arylation and polycyclic sultams via C3 arylation
Sunke, Rajnikanth; Ahmed Khan, Shabbir; Kumara Swamy, K. C.; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01610A

data_7158979
_publ_section_title
;
 Pd-catalysed intramolecular transformations of
 indolylbenzenesulfonamides: ortho-sulfonamido-bi(hetero)aryls via
 C2-arylation and polycyclic sultams via C3 arylation
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01610A
_journal_year                    2022
_chemical_formula_moiety         'C16 H16 N2 O2 S2'
_chemical_formula_sum            'C16 H16 N2 O2 S2'
_chemical_formula_weight         332.43
_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     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2cxcf3
_audit_creation_date             2022-07-19
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_audit_update_record
;
2022-08-17 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.228(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3674(4)
_cell_length_b                   7.8969(3)
_cell_length_c                   19.6001(8)
_cell_measurement_reflns_used    6018
_cell_measurement_temperature    473(200)
_cell_measurement_theta_max      26.3530
_cell_measurement_theta_min      2.0590
_cell_volume                     1568.26(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      473(200)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -53.00 -27.00   0.50    5.00    --  -14.97 -30.00  30.00   52
  2  \w    -35.00  22.00   0.50    5.00    --  -14.97 -94.00  60.00  114
  3  \w    -24.00  19.00   0.50    5.00    --  -14.97 -94.00   0.00   86
  4  \w    -32.00  -7.00   0.50    5.00    --  -14.97 -93.00-107.00   50
  5  \w    -84.00 -56.00   0.50    5.00    --  -14.97 -30.00  30.00   56
  6  \w    -15.00  34.00   0.50    5.00    --  -14.97  93.00   5.00   98
  7  \w     -9.00  17.00   0.50    5.00    --   16.22  93.00   5.00   52
  8  \w    -25.00   5.00   0.50    5.00    --  -14.97  30.00 120.00   60
  9  \w     16.00  56.00   0.50    5.00    --  -14.97  30.00 120.00   80
 10  \w    -36.00 -10.00   0.50    5.00    --   16.22 -94.00 150.00   52
 11  \w     -5.00  53.00   0.50    5.00    --   16.22 -94.00 150.00  116
 12  \w    -34.00  43.00   0.50    5.00    --   16.22 -94.00 120.00  154
 13  \w    -30.00  -4.00   0.50    5.00    --   16.22 -93.00-107.00   52
 14  \w     11.00  42.00   0.50    5.00    --   16.22-125.00-120.00   62
 15  \w    -29.00  -4.00   0.50    5.00    --  -14.97 -94.00-180.00   50
 16  \w    -36.00  44.00   0.50    5.00    --   16.22 -94.00-120.00  160
 17  \w    -59.00 -18.00   0.50    5.00    --  -14.97 125.00-120.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0524739000
_diffrn_orient_matrix_UB_12      0.0518776000
_diffrn_orient_matrix_UB_13      -0.0058323000
_diffrn_orient_matrix_UB_21      0.0458726000
_diffrn_orient_matrix_UB_22      -0.0644825000
_diffrn_orient_matrix_UB_23      0.0136502000
_diffrn_orient_matrix_UB_31      -0.0067417000
_diffrn_orient_matrix_UB_32      -0.0348680000
_diffrn_orient_matrix_UB_33      -0.0339176000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12541
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.065
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0047(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0622P)^2^+0.3697P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2083
_reflns_number_total             2772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01610a2.cif
_cod_data_source_block           Compound12ag
_cod_database_code               7158979
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.68
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O1 \\sim S1: within 1.426A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(O1) = Uanis(S1)
4.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C12(H12), C5(H5), C4(H4), C11(H11)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              98641
_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 5.802
_oxdiff_exptl_absorpt_empirical_full_min 0.438