Stereochemical Surprises in the Lewis Acid-Mediated Allylation of Isatins
Devendra J. Vyas; Roland Fröhlich; Martin Oestreich; Journal of Organic Chemistry 75 (2010) 6720–6723; doi:10.1021/jo101420e

data_4025713
_publ_section_title
;
 Stereochemical Surprises in the Lewis Acid-Mediated Allylation of Isatins
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6720
_journal_page_last               6723
_journal_paper_doi               10.1021/jo101420e
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C26 H24 Cl N O2'
_chemical_formula_weight         417.91
_space_group_IT_number           2
_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                97.222(4)
_cell_angle_beta                 103.333(6)
_cell_angle_gamma                103.505(3)
_cell_formula_units_Z            2
_cell_length_a                   8.6136(6)
_cell_length_b                   9.3565(4)
_cell_length_c                   14.3087(13)
_cell_measurement_reflns_used    3194
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1071.24(14)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrcik, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12684
_diffrn_reflns_theta_full        67.21
_diffrn_reflns_theta_max         67.21
_diffrn_reflns_theta_min         4.95
_exptl_absorpt_coefficient_mu    1.750
_exptl_absorpt_correction_T_max  0.8444
_exptl_absorpt_correction_T_min  0.7552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0069(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0616
_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^)+(0.0683P)^2^+1.3196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1713
_reflns_number_gt                3199
_reflns_number_total             3595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101420e_si_001.cif
_cod_data_source_block           ost5591
_cod_original_cell_volume        1071.24(13)
_cod_database_code               4025713