Design and development of intramolecular doubly vinylogous Michael addition to access 3-aryl substituted 2-alkenyl-benzofurans and -indoles.
Subbi Reddy, Manyam; Nanubolu, Jagadeesh Babu; Suresh, Surisetti; Organic & biomolecular chemistry 21 (2023) 5387–5397; doi:10.1039/d3ob00861d

data_7159452
_publ_section_title
;
 Design and development of intramolecular doubly vinylogous Michael
 addition to access 3-aryl substituted 2-alkenyl-benzofurans and -indoles.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5387
_journal_page_last               5397
_journal_paper_doi               10.1039/d3ob00861d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C31 H34 O4 S'
_chemical_formula_sum            'C31 H34 O4 S'
_chemical_formula_weight         502.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-06-27 deposited with the CCDC.	2023-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.593(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6839(9)
_cell_length_b                   11.2101(6)
_cell_length_c                   15.0773(7)
_cell_measurement_reflns_used    6225
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.520
_cell_measurement_theta_min      2.403
_cell_volume                     2864.4(3)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            55165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.178
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform and Dichloromethane'
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         6585
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1352
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0648P)^2^+1.5797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1720
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3360
_reflns_number_total             6585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00861d2.cif
_cod_data_source_block           kb314_0m_sq
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159452
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              27390
_shelx_fab_checksum              63914