Alpha-hydroxy esters via enantioselective hydrogen-mediated C-C coupling: regiocontrolled reactions of silyl-substituted 1,3-diynes.
Cho, Chang-Woo; Krische, Michael J.; Organic letters 8 (2006) 3873–3876; doi:10.1021/ol061485k

data_1506154
_publ_section_title
;
 Alpha-hydroxy esters via enantioselective hydrogen-mediated C-C coupling:
 regiocontrolled reactions of silyl-substituted 1,3-diynes.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3873
_journal_page_last               3876
_journal_paper_doi               10.1021/ol061485k
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C27 H29 N O2 Si'
_chemical_formula_weight         427.60
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 96.885(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.0952(3)
_cell_length_b                   16.8339(8)
_cell_length_c                   11.9653(6)
_cell_measurement_temperature    153(2)
_cell_volume                     1218.86(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    0.0539
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5399
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.9698
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_extinction_coef       0.022(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   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5399
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.565
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0339P)^2^+0.0940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0859
_reflns_number_gt                4393
_reflns_number_total             5399
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061485krom20060616_123023.cif
_cod_data_source_block           tms606
_cod_database_code               1506154