Catalytic enantioselective addition of terminal alkynes to aromatic aldehydes using zinc-hydroxyamide complexes
Blay, Gonzalo; Cardona, Luz; Fernández, Isabel; Marco-Aleixandre, Alícia; Muñoz, M. Carmen; Pedro, José R.; Organic & Biomolecular Chemistry 7 (2009) 4301–4308; doi:10.1039/b911592g

data_7150744
_publ_section_title
;
 Catalytic enantioselective addition of terminal alkynes to aromatic
 aldehydes using zinc-hydroxyamide complexes
;
_journal_issue                   20
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4301
_journal_page_last               4308
_journal_paper_doi               10.1039/b911592g
_journal_volume                  7
_journal_year                    2009
_chemical_formula_sum            'C22 H25 N O2'
_chemical_formula_weight         335.43
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_cell_angle_beta                 108.2480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9740(3)
_cell_length_b                   8.8110(3)
_cell_length_c                   12.1490(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1013.97(6)
_computing_cell_refinement       'HKL DENZO'
_computing_data_collection       COLLECT
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0957
_diffrn_reflns_av_sigmaI/netI    0.0988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8581
_diffrn_reflns_theta_full        26.74
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.070
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.054
_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       0.025(9)
_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   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0683
_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^)+(0.1126P)^2^+0.0977P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.2119
_reflns_number_gt                2557
_reflns_number_total             4178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b911592g.txt
_cod_data_source_block           ja489
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7150744