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_1545459
_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_absolute_configuration ad
_chemical_formula_sum            'C18 H14 Br N2 O2'
_chemical_formula_weight         370.22
_chemical_name_common            FC-4d
_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
_cell_angle_alpha                90
_cell_angle_beta                 108.402(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0525(12)
_cell_length_b                   8.6536(12)
_cell_length_c                   10.8768(14)
_cell_measurement_reflns_used    2986
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.80
_cell_measurement_theta_min      2.37
_cell_volume                     808.48(19)
_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      296
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.928
_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  0.0172
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4611
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.418
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.553
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.458
_refine_ls_abs_structure_details
;
Flack x determined using 836 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2935
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0239
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0581
_reflns_number_gt                2732
_reflns_number_total             2935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03584_si_002.cif
_cod_data_source_block           I
_cod_database_code               1545459
_shelx_res_checksum              32075
_shelx_hkl_checksum              34825