Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines
Alam, Rauful; Das, Arindam; Huang, Genping; Eriksson, Lars; Himo, Fahmi; Szabó, Kálmán J.; Chemical Science 5 (2014) 2732–; doi:10.1039/c4sc00415a

data_1515886
_publ_section_title
;
 Stereoselective allylboration of imines and indoles under mild
 conditions. An in situ E/Z isomerization of imines by allylboroxines
;
_journal_issue                   7
_journal_name_full               'Chemical Science'
_journal_page_first              2732
_journal_paper_doi               10.1039/c4sc00415a
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C22 H20 Br N O2 S'
_chemical_formula_weight         442.36
_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                89.74(2)
_cell_angle_beta                 87.38(3)
_cell_angle_gamma                85.551(18)
_cell_formula_units_Z            4
_cell_length_a                   6.9028(18)
_cell_length_b                   11.787(2)
_cell_length_c                   25.657(12)
_cell_measurement_reflns_used    373
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.3240
_cell_measurement_theta_min      3.4250
_cell_volume                     2079.1(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.5467
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans at different \f to fill Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_av_sigmaI/netI    0.1675
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4148
_diffrn_reflns_theta_full        15.86
_diffrn_reflns_theta_max         15.86
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    2.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         2.144
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       0.0000(17)
_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   1.265
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         1937
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.257
_refine_ls_R_factor_all          0.2131
_refine_ls_R_factor_gt           0.1624
_refine_ls_shift/su_max          1.342
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3726
_refine_ls_wR_factor_ref         0.4133
_reflns_number_gt                1183
_reflns_number_total             1937
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c4sc00415a2.cif
_cod_data_source_block           r_3d
_cod_depositor_comments
'Adding full bibliography for 1515885--1515887.cif.'
_cod_original_cell_volume        2079.0(12)
_cod_database_code               1515886