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_7159453
_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         'C37 H39 N O5 S2'
_chemical_formula_sum            'C37 H39 N O5 S2'
_chemical_formula_weight         641.81
_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
;
2023-03-30 deposited with the CCDC.	2023-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.109(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.294(2)
_cell_length_b                   19.579(4)
_cell_length_c                   17.114(3)
_cell_measurement_reflns_used    6766
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.555
_cell_measurement_theta_min      2.257
_cell_volume                     3405.8(11)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37337
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.258
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6733
_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_colour            COLORLESS
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile and Hexane (1:1)'
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7766
_refine_ls_number_restraints     210
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0445P)^2^+1.6167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1392
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4068
_reflns_number_total             7766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00861d2.cif
_cod_data_source_block           KB789_0m
_cod_original_cell_volume        3405.9(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159453
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.965
_shelx_res_checksum              29253