Asymmetric Organocatalytic Monofluorovinylations
Jacobsen, Christian Borch; Nielsen, Martin; Worgull, Dennis; Zweifel, Theo; Fisker, Esben; Jørgensen, Karl Anker; Journal of the American Chemical Society 133 (2011) 7398–7404; doi:10.1021/ja110624k

data_4121888
_publ_section_title
;
 Asymmetric Organocatalytic Monofluorovinylations
;
_journal_coden_ASTM              JACSAT
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7398
_journal_page_last               7404
_journal_paper_doi               10.1021/ja110624k
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H14 Br F O'
_chemical_formula_weight         297.16
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date
;
'Thu Oct 28 09:35:23 2010'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
;
_cell_angle_alpha                70.347(2)
_cell_angle_beta                 89.0054(19)
_cell_angle_gamma                83.0633(19)
_cell_formula_units_Z            2
_cell_length_a                   5.60760(13)
_cell_length_b                   9.3875(2)
_cell_length_c                   12.8524(3)
_cell_measurement_reflns_used    13978
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2630
_cell_measurement_theta_min      2.3164
_cell_volume                     632.30(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3590
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27513
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.33
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.39 (release 18-08-2010 CrysAlis171 .NET)
(compiled Aug 18 2010,17:42:00)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.043
_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   0.826
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         6201
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.826
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                5156
_reflns_number_total             6201
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4106130
_cod_data_source_file            ja110624k_si_002.cif
_cod_data_source_block           shelxl
_cod_database_code               4121888