Rhodium-catalyzed regioselective opening of vinyl epoxides with Et3N·3HF reagent – formation of allylic fluorohydrins
Zhang, Qi; Nguyen, Hien M.; Chemical Science 5 (2014) 291–; doi:10.1039/c3sc51949j

data_1513712
_publ_section_title
;
 Rhodium-catalyzed regioselective opening of vinyl epoxides with
 Et3N&#x00B7;3HF reagent -- formation of allylic fluorohydrins
;
_journal_issue                   1
_journal_name_full               'Chemical Science'
_journal_page_first              291
_journal_paper_doi               10.1039/c3sc51949j
_journal_volume                  5
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H13 Br F2 O2'
_chemical_formula_sum            'C17 H13 Br F2 O2'
_chemical_formula_weight         367.18
_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                 93.183(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.0913(18)
_cell_length_b                   7.5678(8)
_cell_length_c                   22.361(2)
_cell_measurement_reflns_used    13636
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.0
_cell_volume                     3056.8(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL v6.1  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.1  (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL v6.1  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL v6.1  (Sheldrick, 2008)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ccd 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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            72549
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.714
_exptl_absorpt_correction_T_max  0.7730
_exptl_absorpt_correction_T_min  0.4678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     815
_refine_ls_number_reflns         13519
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+0.6688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0856
_reflns_number_gt                9917
_reflns_number_total             13519
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc51949j.txt
_cod_data_source_block           ngu131a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_Hall     'P 2yb '
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               1513712