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_7158976
_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 S'
_chemical_formula_sum            'C16 H16 N2 O2 S'
_chemical_formula_weight         300.37
_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.cc2cxc9z
_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                 101.2610(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6333(5)
_cell_length_b                   11.3408(5)
_cell_length_c                   11.7715(5)
_cell_measurement_reflns_used    8609
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.07
_cell_measurement_theta_min      2.52
_cell_volume                     1523.13(11)
_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_temperature      293.23
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            49284
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.251
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             632
_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         0.396
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0044(8)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0377P)^2^+1.2416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2022
_reflns_number_total             2683
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01610a2.cif
_cod_data_source_block           Compound9ba
_cod_database_code               7158976
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C2(H2), C10(H10), N2(H2A), C11(H11), C7(H7), C4(H4), C3(H3),
 C12(H12), C5(H5)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              6929
_olex2_submission_special_instructions 'No special instructions were received'