Enantioselective synthesis of trifluoromethyl-substituted cyclopropanes.
Denton, Justin R.; Sukumaran, Dinesh; Davies, Huw M. L.; Organic letters 9 (2007) 2625–2628; doi:10.1021/ol070714f

data_1505410
_publ_section_title
;
 Enantioselective synthesis of trifluoromethyl-substituted cyclopropanes.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              2625
_journal_page_last               2628
_journal_paper_doi               10.1021/ol070714f
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H16 Br2 F3 N O'
_chemical_formula_sum            'C23 H16 Br2 F3 N O'
_chemical_formula_weight         539.19
_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                 113.2340(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.5320(5)
_cell_length_b                   5.4471(2)
_cell_length_c                   15.2633(6)
_cell_measurement_reflns_used    6102
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      31.684
_cell_measurement_theta_min      2.583
_cell_volume                     1033.82(7)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        SADABS(Sheldrick,2004)
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'APEXII CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32085
_diffrn_reflns_theta_full        33.24
_diffrn_reflns_theta_max         33.24
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    3.962
_exptl_absorpt_correction_T_max  0.6927
_exptl_absorpt_correction_T_min  0.5046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2004/1; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.338
_refine_diff_density_min         -1.727
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         7857
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0314P)^2^+1.2957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                6836
_reflns_number_total             7857
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070714fsi20070418_034814.cif
_cod_data_source_block           JD-4-BramideCyclopropaneCF3Br
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1505410