Enantioselective synthesis of polycyclic nitrogen heterocycles by rh-catalyzed alkene hydroacylation: constructing six-membered rings in the absence of chelation assistance.
Du, Xiang-Wei; Ghosh, Avipsa; Stanley, Levi M.; Organic letters 16 (2014) 4036–4039; doi:10.1021/ol501869s

data_1517120
_publ_section_title
;
 Enantioselective synthesis of polycyclic nitrogen heterocycles by
 rh-catalyzed alkene hydroacylation: constructing six-membered rings in
 the absence of chelation assistance.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              4036
_journal_page_last               4039
_journal_paper_doi               10.1021/ol501869s
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_sum            'C13 H12 Br N O'
_chemical_formula_weight         278.15
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2012.4-3'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6803(4)
_cell_length_b                   10.1921(6)
_cell_length_c                   16.8279(10)
_cell_measurement_reflns_used    5726
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      28.4648
_cell_measurement_theta_min      2.3362
_cell_volume                     1145.75(12)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  ' BRUKER APEX2 CCD Diffractometer'
_diffrn_measurement_method       '\w scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12242
_diffrn_reflns_theta_full        28.80
_diffrn_reflns_theta_max         28.80
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    3.564
_exptl_absorpt_correction_T_max  0.52
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.396
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0253P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0497
_refine_ls_wR_factor_ref         0.0506
_reflns_number_gt                2684
_reflns_number_total             2966
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501869s_si_002.cif
_cod_data_source_block           I
_cod_depositor_comments          'Adding full bibliography for 1517120.cif.'
_cod_database_code               1517120