Asymmetric synthesis of N,O-heterocycles via enantioselective iridium-catalysed intramolecular allylic amidation
Zhao, Depeng; Fañanás-Mastral, Martín; Chang, Mu-Chieh; Otten, Edwin; Feringa, Ben L.; Chem. Sci. 5 (2014) 4216–; doi:10.1039/C4SC01940G

data_1517195
_publ_section_title
;
 Asymmetric synthesis of N,O-heterocycles via enantioselective
 iridium-catalysed intramolecular allylic amidation
;
_journal_issue                   11
_journal_name_full               'Chem. Sci.'
_journal_page_first              4216
_journal_paper_doi               10.1039/C4SC01940G
_journal_volume                  5
_journal_year                    2014
_chemical_formula_sum            'C16 H12 Br N O'
_chemical_formula_weight         314.18
_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                85.222(3)
_cell_angle_beta                 78.520(3)
_cell_angle_gamma                70.043(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3154(5)
_cell_length_b                   8.1371(7)
_cell_length_c                   14.3362(12)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      53.933
_cell_measurement_theta_min      5.801
_cell_volume                     678.53(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0332
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31603
_diffrn_reflns_theta_full        27.13
_diffrn_reflns_theta_max         27.13
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    3.019
_exptl_absorpt_correction_T_max  0.7728
_exptl_absorpt_correction_T_min  0.5697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.972
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5756
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0552
_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^)+(0.1061P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1434
_reflns_number_gt                4785
_reflns_number_total             5756
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc01940g2.cif
_cod_data_source_block           mo_molan093c_0m
_cod_depositor_comments
'Adding full bibliography for 1517194--1517195.cif.'
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1517195