Diastereoselective synthesis of <i>trans</i>-2,3-dihydroindoles <i>via</i> formal [4 + 1] annulation reactions of a sulfonium ylide.
Jain, Anshul; Kumari, Akanksha; Metre, Ramesh K.; Rana, Nirmal K.; Organic & biomolecular chemistry 22 (2024) 621–632; doi:10.1039/d3ob01793a

data_7159723
_publ_section_title
;
 Diastereoselective synthesis of <i>trans</i>-2,3-dihydroindoles
 <i>via</i> formal [4 + 1] annulation reactions of a sulfonium ylide.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              621
_journal_page_last               632
_journal_paper_doi               10.1039/d3ob01793a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C30 H25 N O4 S'
_chemical_formula_sum            'C30 H25 N O4 S'
_chemical_formula_weight         495.57
_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     direct
_audit_creation_date             2022-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-06-11 deposited with the CCDC.	2023-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.685(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1168(14)
_cell_length_b                   17.929(3)
_cell_length_c                   16.686(3)
_cell_measurement_reflns_used    9132
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.45
_cell_volume                     2420.1(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.987
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            35876
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.392
_diffrn_reflns_theta_min         2.762
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1065 before and 0.0639 after correction.
The Ratio of minimum to maximum transmission is 0.9338.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       block
_exptl_crystal_F_000             1040.0
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0444
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1522
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5223
_reflns_number_total             5987
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01793a2.cif
_cod_data_source_block           23apra_0m
_cod_depositor_comments          'Adding full bibliography for 7159723.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7159723
_shelx_shelxl_version_number     2018/3
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C28(H28), C29(H29)
2.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_shelx_res_checksum              73197
_olex2_submission_special_instructions 'No special instructions were received'