First Catalytic Reductive Coupling of 1,3-Diynes to Carbonyl Partners: A New Regio- and Enantioselective C-C Bond Forming Hydrogenation
Ryan R. Huddleston; Hye-Young Jang; Michael J. Krische; Journal of the American Chemical Society 125 (2003) 11488–11489; doi:10.1021/ja030415v

data_4114175
_publ_section_title
;
 First Catalytic Reductive Coupling of 1,3-Diynes to Carbonyl Partners: A
 New Regio- and Enantioselective C-C Bond Forming Hydrogenation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11488
_journal_page_last               11489
_journal_paper_doi               10.1021/ja030415v
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C24 H18 O2'
_chemical_formula_weight         338.38
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7781(2)
_cell_length_b                   15.2090(4)
_cell_length_c                   20.4982(7)
_cell_measurement_temperature    153(2)
_cell_volume                     1801.36(10)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4102
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'faint yellow'
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       'clusters of needles'
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_coef       0.031(2)
_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   1.143
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0190P)^2^+0.8230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                2760
_reflns_number_total             4102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja030415v.cif
_cod_data_source_block           JA030415V
_cod_database_code               4114175