Catalytic Asymmetric Synthesis of Chiral 2-Vinylindole Scaffolds by Friedel-Crafts Reaction.
Arai, Takayoshi; Tsuchida, Akiko; Miyazaki, Tomoya; Awata, Atsuko; Organic letters 19 (2017) 758–761; doi:10.1021/acs.orglett.6b03584

data_1545171
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Chiral 2-Vinylindole Scaffolds by
 Friedel-Crafts Reaction.
;
_journal_issue                   4
_journal_name_full               'Organic letters'
_journal_page_first              758
_journal_page_last               761
_journal_paper_doi               10.1021/acs.orglett.6b03584
_journal_volume                  19
_journal_year                    2017
_chemical_formula_sum            'C20 H17 N2 O4'
_chemical_formula_weight         349.35
_chemical_name_common            Tsuchida-02
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 107.296(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.711(5)
_cell_length_b                   5.6403(7)
_cell_length_c                   9.9643(13)
_cell_measurement_reflns_used    2943
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.6620
_cell_measurement_theta_min      2.6086
_cell_volume                     1755.3(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5088
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.570
_diffrn_reflns_theta_min         1.30
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.700
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.355
_refine_ls_abs_structure_details
;
Flack x determined using 949 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(10)
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3335
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.241
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.9214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                3022
_reflns_number_total             3335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03584_si_003.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1545171.cif.'
_cod_database_code               1545171
_shelx_res_checksum              4603
_shelx_hkl_checksum              33823