Atom-economical and workup-free multiparticipation of p-TsOH in yne-ynamide skeletal reshuffle: access to regiospecific, chemospecific, and stereospecific (E)-alkenyl sulfonate/ketone-tethered indoles
Mutra, Mohana Reddy; Chandana, T. L.; Wang, Jeh-Jeng; Green Chemistry 27 (2025) 1062–1072; doi:10.1039/D4GC05876C

data_7249694
_publ_section_title
;
 Atom-economical and workup-free multiparticipation of p-TsOH in
 yne-ynamide skeletal reshuffle: access to regiospecific, chemospecific,
 and stereospecific (E)-alkenyl sulfonate/ketone-tethered indoles
;
_journal_issue                   4
_journal_name_full               'Green Chemistry'
_journal_page_first              1062
_journal_page_last               1072
_journal_paper_doi               10.1039/D4GC05876C
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C29 H23 N O3 S'
_chemical_formula_sum            'C29 H23 N O3 S'
_chemical_formula_weight         465.54
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2024-08-13 deposited with the CCDC.	2024-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.4449(14)
_cell_length_b                   8.4715(3)
_cell_length_c                   17.0615(7)
_cell_measurement_reflns_used    8803
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.76
_cell_measurement_theta_min      2.49
_cell_volume                     4689.5(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26420
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_correction_T_min  0.9305
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+0.8769P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1296
_reflns_number_gt                3478
_reflns_number_total             4300
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4gc05876c2.cif
_cod_data_source_block           d25047
_cod_depositor_comments
'Adding full bibliography for 7249694--7249695.cif.'
_cod_database_code               7249694