Enantioselective Friedel-Crafts alkylation for synthesis of 2-substituted indole derivatives
Yulong Zhang; Xiaohua Liu; Xiaohu Zhao; Jianlin Zhang; Lin Zhou; Lili Lin; Xiaoming Feng; Chem.Commun. 49 (2013) 11311–; doi:10.1039/c3cc45665j

data_7110062
_publ_section_title
;
 Enantioselective Friedel-Crafts alkylation for synthesis of 2-substituted
 indole derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              11311
_journal_paper_doi               10.1039/c3cc45665j
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 F N2 O3'
_chemical_formula_sum            'C21 H21 F N2 O3'
_chemical_formula_weight         368.40
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.40(4)
_cell_angle_beta                 77.72(5)
_cell_angle_gamma                82.79(5)
_cell_formula_units_Z            2
_cell_length_a                   7.509(7)
_cell_length_b                   9.895(6)
_cell_length_c                   13.071(6)
_cell_measurement_reflns_used    4210
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.20
_cell_volume                     931.6(11)
_computing_cell_refinement       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_collection       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_reduction        'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14843
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.50
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi March, 2001'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.55
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         5757
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0901
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+1.6117P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1885
_refine_ls_wR_factor_ref         0.1976
_reflns_number_gt                5074
_reflns_number_total             5757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc45665j.txt
_cod_data_source_block           sx3003
_cod_original_sg_symbol_H-M      P1
_cod_database_code               7110062