Stereoselective Construction of Halogenated Quaternary Stereogenic Centers via Catalytic Asymmetric Diels−Alder Reaction
Shibatomi, Kazutaka; Futatsugi, Kentaro; Kobayashi, Fumito; Iwasa, Seiji; Yamamoto, Hisashi; Journal of the American Chemical Society 132 (2010) 5625–5627; doi:10.1021/ja1018628

data_4119117
_publ_section_title
;
 Stereoselective Construction of Halogenated Quaternary Stereogenic
 Centers via Catalytic Asymmetric Diels&#x2212;Alder Reaction
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5625
_journal_page_last               5627
_journal_paper_doi               10.1021/ja1018628
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C19 H23 Br F N O'
_chemical_formula_weight         380.29
_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                 103.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3406(19)
_cell_length_b                   12.461(3)
_cell_length_c                   15.759(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1782.4(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0741
_diffrn_reflns_av_sigmaI/netI    0.1112
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14208
_diffrn_reflns_theta_full        23.51
_diffrn_reflns_theta_max         23.51
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    2.320
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.048(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.683
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5209
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.683
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.188
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1103P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1302
_reflns_number_gt                3743
_reflns_number_total             5209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja1018628sup2.cif
_cod_data_source_block           hyamaz
_cod_original_cell_volume        1782.4(6)
_cod_database_code               4119117