Trienamine catalysed unprecedented remote olefin <i>E</i>/<i>Z</i> isomerisation/[4 + 2]-cycloaddition reaction to access spirooxindole hexahydroindoles.
Prasad, Madavi S.; Sivaprakash, Murugesan; Bharani, Sankar; Chowhan, L. Raju; Organic & biomolecular chemistry 21 (2023) 945–949; doi:10.1039/d2ob02228a

data_7159073
_publ_section_title
;
 Trienamine catalysed unprecedented remote olefin <i>E</i>/<i>Z</i>
 isomerisation/[4 + 2]-cycloaddition reaction to access spirooxindole
 hexahydroindoles.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              945
_journal_page_last               949
_journal_paper_doi               10.1039/d2ob02228a
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H35 Cl N2 O7 S'
_chemical_formula_sum            'C36 H35 Cl N2 O7 S'
_chemical_formula_weight         675.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-29 deposited with the CCDC.	2022-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.170(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.5446(12)
_cell_length_b                   7.9372(6)
_cell_length_c                   15.4692(13)
_cell_measurement_reflns_used    5557
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.91
_cell_volume                     1706.2(2)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       '\w and \f scan'
_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  0.1250
_diffrn_reflns_av_unetI/netI     0.0910
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30192
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         3.380
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.4388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       ROD
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.401
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1473 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6329
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0432P)^2^+0.0508P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1314
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4385
_reflns_number_total             6329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02228a4.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7159073.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159073
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              63787