Organocatalytic asymmetric reaction of indol-2-yl carbinols with enamides: synthesis of chiral 2-indole-substituted 1,1-diarylalkanes
Chao-You Liu; Fu-She Han; Chem.Commun. 51 (2015) 11844–; doi:10.1039/C5cc03345D

data_7117468
_publ_section_title
;
 Organocatalytic asymmetric reaction of indol-2-yl carbinols with
 enamides: synthesis of chiral 2-indole-substituted 1,1-diarylalkanes
;
_journal_name_full               Chem.Commun.
_journal_page_first              11844
_journal_paper_doi               10.1039/C5cc03345D
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C35 H36 Br N3 O3 S'
_chemical_formula_sum            'C35 H36 Br N3 O3 S'
_chemical_formula_weight         658.64
_chemical_name_systematic        lcy-Q-103
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-04 deposited with the CCDC.
2015-06-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.930(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4805(11)
_cell_length_b                   15.3417(19)
_cell_length_c                   11.8162(14)
_cell_measurement_temperature    293(2)
_cell_volume                     1594.3(3)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0814
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10385
_diffrn_reflns_theta_full        26.05
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    1.394
_exptl_absorpt_correction_T_max  0.8181
_exptl_absorpt_correction_T_min  0.7679
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            coloress
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Trichloromethane and petroleum ether'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.008(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6126
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0710P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                5145
_reflns_number_total             6126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc03345d2.cif
_cod_data_source_block           z063m
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7117468