Catalytic Enantioselective Grignard Nozaki-Hiyama Methallylation from the Alcohol Oxidation Level: Chloride Compensates for p-Complex Instability
Abbas Hassan; Ian A. Townsend; Michael Krische; Chem.Commun. 47 (2011) 10028–; doi:10.1039/c1cc14392a

data_7106831
_publ_section_title
;
 Catalytic Enantioselective Grignard Nozaki-Hiyama Methallylation from the
 Alcohol Oxidation Level: Chloride Compensates for p-Complex Instability
;
_journal_name_full               Chem.Commun.
_journal_page_first              10028
_journal_paper_doi               10.1039/c1cc14392a
_journal_volume                  47
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H13 Br O'
_chemical_formula_sum            'C11 H13 Br O'
_chemical_formula_weight         241.12
_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                90.00
_cell_angle_beta                 105.335(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.2407(9)
_cell_length_b                   5.1056(6)
_cell_length_c                   11.6424(12)
_cell_measurement_reflns_used    1629
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.0
_cell_volume                     529.72(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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     0.71075
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8793
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    3.839
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_correction_T_min  0.413
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
N.W. Alcock (1970). Cryst. Computing, p271
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.036(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3030
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0223P)^2^+0.3520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                2188
_reflns_number_total             3030
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc14392a.txt
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7106831