A Diels-Alder approach to the enantioselective construction of fluoromethylated stereogenic carbon centers
Kazutaka Shibatomi; Fumito Kobayashi; Akira Narayama; Ikuhide Fujisawa; Seiji Iwasa; Chem.Commun. 48 (2012) 413–; doi:10.1039/c1cc15889a

data_7107162
_publ_section_title
;
 A Diels-Alder approach to the enantioselective construction of
 fluoromethylated stereogenic carbon centers
;
_journal_name_full               Chem.Commun.
_journal_page_first              413
_journal_paper_doi               10.1039/c1cc15889a
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H16 Br F3 O3'
_chemical_formula_sum            'C21 H16 Br F3 O3'
_chemical_formula_weight         453.25
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.260(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0606(18)
_cell_length_b                   12.444(3)
_cell_length_c                   21.593(6)
_cell_measurement_reflns_used    5027
_cell_measurement_temperature    295.00
_cell_measurement_theta_max      30.3678
_cell_measurement_theta_min      2.5014
_cell_volume                     1892.0(8)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 2004 (Burla, Caliandro et al., 2005)'
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type
'4-circle diffractometer, Rigaku Mercury CCD camera(2x2 bin mode)'
_diffrn_measurement_method       dtintegrate.ref
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14279
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3590
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.6000
_exptl_crystal_size_mid          0.5000
_exptl_crystal_size_min          0.1000
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(8)
_refine_ls_extinction_coef       0.0092(15)
_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   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         6814
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0740P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1277
_reflns_number_gt                5343
_reflns_number_total             6814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc15889a.txt
_cod_data_source_block           shib32
_cod_original_cell_volume        1891.9(8)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7107162