Branch-Selective Reductive Coupling of 2-Vinyl Pyridines and Imines via Rhodium Catalyzed C-C Bond Forming Hydrogenation
Venukrishnan Komanduri; Christopher D. Grant; Michael J. Krische; Journal of the American Chemical Society 130 (2008) 12592–12593; doi:10.1021/ja805056g

data_4108374
_publ_section_title
;
 Branch-Selective Reductive Coupling of 2-Vinyl Pyridines and Imines via
 Rhodium Catalyzed C-C Bond Forming Hydrogenation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12592
_journal_page_last               12593
_journal_paper_doi               10.1021/ja805056g
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C19 H19 Br N2 O2 S2'
_chemical_formula_weight         451.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.334(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6171(3)
_cell_length_b                   12.0557(4)
_cell_length_c                   15.7265(7)
_cell_measurement_reflns_used    4255
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1910.76(12)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w-scans
_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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8165
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    2.386
_exptl_absorpt_correction_T_max  0.56
_exptl_absorpt_correction_T_min  0.47
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       prisms
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0010(3)
_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   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0321P)^2^+1.1485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                3645
_reflns_number_total             4366
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja805056g_si_001.cif
_cod_data_source_block           br1
_cod_database_code               4108374