Application of 3-Methyl-2-vinylindoles in Catalytic Asymmetric Povarov Reaction: Diastereo- and Enantioselective Synthesis of Indole-Derived Tetrahydroquinolines.
Dai, Wei; Jiang, Xiao-Li; Tao, Ji-Yu; Shi, Feng; The Journal of organic chemistry 81 (2016) 185–192; doi:10.1021/acs.joc.5b02476

data_4031762
_publ_section_title
;
 Application of 3-Methyl-2-vinylindoles in Catalytic Asymmetric Povarov
 Reaction: Diastereo- and Enantioselective Synthesis of Indole-Derived
 Tetrahydroquinolines.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              185
_journal_page_last               192
_journal_paper_doi               10.1021/acs.joc.5b02476
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C31 H27 N3 O3'
_chemical_formula_sum            'C31 H27 N3 O3'
_chemical_formula_weight         489.55
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.265(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.5466(2)
_cell_length_b                   9.2228(3)
_cell_length_c                   20.4337(7)
_cell_measurement_reflns_used    5770
_cell_measurement_temperature    130
_cell_measurement_theta_max      68.862
_cell_measurement_theta_min      4.373
_cell_volume                     1220.93(7)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8792
_diffrn_reflns_point_group_measured_fraction_full 0.837
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.573
_diffrn_reflns_theta_min         2.185
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0564 after correction.
The Ratio of minimum to maximum transmission is 0.7181.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 1317 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0685
_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^)+(0.0947P)^2^+2.1435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2010
_refine_ls_wR_factor_ref         0.2015
_reflns_Friedel_coverage         0.577
_reflns_Friedel_fraction_full    0.664
_reflns_Friedel_fraction_max     0.639
_reflns_number_gt                3665
_reflns_number_total             3747
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b02476_si_002.cif
_cod_data_source_block           cu_dm15304_0m
_cod_depositor_comments          'Adding full bibliography for 4031762.cif.'
_cod_database_code               4031762
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C30(H30),
  C31(H31)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              54070
_shelx_hkl_checksum              33835
_olex2_submission_special_instructions 'No special instructions were received'