Highly enantioselective monofluoromethylation of C2-arylindoles using FBSM under chiral phase-transfer catalysis.
Matsuzaki, Kohei; Furukawa, Tatsuya; Tokunaga, Etsuko; Matsumoto, Takashi; Shiro, Motoo; Shibata, Norio; Organic letters 15 (2013) 3282–3285; doi:10.1021/ol4013102

data_1556187
_publ_section_title
;
 Highly enantioselective monofluoromethylation of C2-arylindoles using
 FBSM under chiral phase-transfer catalysis.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3282
_journal_page_last               3285
_journal_paper_doi               10.1021/ol4013102
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H26 F N O4 S2'
_chemical_formula_sum            'C34 H26 F N O4 S2'
_chemical_formula_weight         595.70
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.641(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   9.5437(16)
_cell_length_b                   15.151(3)
_cell_length_c                   10.6193(19)
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    93
_cell_measurement_theta_max      50.27
_cell_measurement_theta_min      4.48
_cell_volume                     1427.3(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku, 2000-2010)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku, 2000-2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6636
_diffrn_reflns_theta_full        50.38
_diffrn_reflns_theta_max         50.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.088
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             620.00
_exptl_crystal_size_max          0.048
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.270
_refine_diff_density_min         -0.340
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1302 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     319
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     44
_refine_ls_R_factor_gt           0.0803
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1265P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2070
_reflns_number_gt                2359
_reflns_number_total             2854
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol4013102_si_001.cif
_cod_data_source_block           SX139
_cod_database_code               1556187
_verf_thetm01_alert_3_a
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
         Calculated sin(theta_max)/wavelength = 0.4996
RESPONSE: Low-resolution reflection data used, see _publ_section_
          exptl_refinement
;