Enantioselective gem-chlorofluorination of active methylene compounds using a chiral spiro oxazoline ligand.
Shibatomi, Kazutaka; Narayama, Akira; Soga, Yoshinori; Muto, Tsubasa; Iwasa, Seiji; Organic letters 13 (2011) 2944–2947; doi:10.1021/ol201007e

data_1502220
_publ_section_title
;
 Enantioselective gem-chlorofluorination of active methylene compounds
 using a chiral spiro oxazoline ligand.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2944
_journal_page_last               2947
_journal_paper_doi               10.1021/ol201007e
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C11 H10 Cl F O4'
_chemical_formula_sum            'C11 H10 Cl F O4'
_chemical_formula_weight         260.64
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.709(11)
_cell_angle_beta                 76.761(10)
_cell_angle_gamma                81.899(9)
_cell_formula_units_Z            4
_cell_length_a                   8.3700(12)
_cell_length_b                   11.7321(19)
_cell_length_c                   12.650(2)
_cell_measurement_reflns_used    4485
_cell_measurement_temperature    293.1500
_cell_measurement_theta_max      27.0945
_cell_measurement_theta_min      2.4890
_cell_volume                     1194.8(3)
_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      293.1500
_diffrn_detector_area_resol_mean 14.7059
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_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_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7854
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.49
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7449
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.4000
_exptl_crystal_size_mid          0.4000
_exptl_crystal_size_min          0.2000
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+0.3187P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1123
_reflns_number_gt                2891
_reflns_number_total             3223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201007e_si_003.cif
_cod_data_source_block           shib13
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_database_code               1502220