Enantioselective dearomative [3 + 2] cycloadditions of indoles with azomethine ylides derived from alanine imino esters
Gerten, Anthony L.; Stanley, Levi M.; Organic Chemistry Frontiers 3 (2016) 339–; doi:10.1039/C5QO00346F

data_1553206
_publ_section_title
;
 Enantioselective dearomative [3 + 2] cycloadditions of indoles with
 azomethine ylides derived from alanine imino esters
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              339
_journal_paper_doi               10.1039/C5QO00346F
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H28 Br N3 O7 S'
_chemical_formula_weight         618.49
_chemical_name_systematic
'methyl (1S,3R,3aS,8bS)-1-(4-methoxyphenyl)-3-methyl-8b-nitro-4-tosyl-1,2,3,3a,4,8b-hexahydropyrrolo[3,4-b]indole-3-carboxylate'
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2015-10-30 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.4240(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0065(9)
_cell_length_b                   8.7880(7)
_cell_length_c                   14.4392(12)
_cell_measurement_reflns_used    6977
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      27.2914
_cell_measurement_theta_min      2.5380
_cell_volume                     1377.78(19)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2013)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2013)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2013)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ' full spere \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18104
_diffrn_reflns_theta_full        27.58
_diffrn_reflns_theta_max         27.58
_diffrn_reflns_theta_min         1.43
_diffrn_source                   'X-ray tuve'
_diffrn_source_type              'Sealed tube'
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_T_max  0.82
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and dichloromethane'
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.193
_refine_ls_abs_structure_details
;
Flack x determined using 2411 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         6360
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0275
_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^)+(0.0321P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                5705
_reflns_number_total             6360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5qo00346f2.cif
_cod_data_source_block           I
_cod_database_code               1553206
_shelx_res_checksum              48555
_shelx_hkl_checksum              46678