Synthesis of a-fluoro-B-hydroxy esters by an enantioselective Reformatsky-type reaction
Michal Fornalczyk; Kuldip Singh; Alison M. Stuart; Chem.Commun. 48 (2012) 3500–; doi:10.1039/c2cc17985g

data_7107515
_publ_section_title
;
 Synthesis of a-fluoro-B-hydroxy esters by an enantioselective
 Reformatsky-type reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              3500
_journal_paper_doi               10.1039/c2cc17985g
_journal_volume                  48
_journal_year                    2012
_chemical_absolute_configuration ,syn
_chemical_formula_moiety         'C18 H20 F N O2'
_chemical_formula_sum            'C18 H20 F N O2'
_chemical_formula_weight         301.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.306(3)
_cell_length_b                   9.746(3)
_cell_length_c                   18.935(6)
_cell_measurement_reflns_used    685
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      20.337
_cell_measurement_theta_min      2.351
_cell_volume                     1532.8(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0879
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11981
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
absorption correction based on 4760 reflections(SADABS);Rint 0.0806 before
correction and 0.0454 after.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0374P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                1506
_reflns_number_total             1750
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc17985g.txt
_cod_data_source_block           11009
_cod_original_cell_volume        1532.7(8)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7107515