Enantioselective synthesis of fluorinated branched allylic compounds via Ir-catalyzed allylations of functionalized fluorinated methylene derivatives.
Zhang, Hongbo; Chen, Jiteng; Zhao, Xiao-Ming; Organic & biomolecular chemistry 14 (2016) 7183–7186; doi:10.1039/c6ob01246a

data_7155182
_publ_section_title
;
 Enantioselective synthesis of fluorinated branched allylic compounds via
 Ir-catalyzed allylations of functionalized fluorinated methylene
 derivatives.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7183
_journal_page_last               7186
_journal_paper_doi               10.1039/c6ob01246a
_journal_volume                  14
_journal_year                    2016
_chemical_compound_source        'man made'
_chemical_formula_moiety         'C14 H14 Br F O4'
_chemical_formula_sum            'C14 H14 Br F O4'
_chemical_formula_weight         345.16
_chemical_name_common            no
_chemical_name_systematic
'Dimethyl-2-(1-(4-bromophenyl)allyl)-2-fluoromalonate '
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-05-09 deposited with the CCDC.
2016-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.578(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6347(7)
_cell_length_b                   5.7454(4)
_cell_length_c                   25.1891(15)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.54
_cell_measurement_theta_min      4.17
_cell_volume                     1534.16(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-III COMS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13577
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        66.586
_diffrn_reflns_theta_max         66.585
_diffrn_reflns_theta_min         3.520
_exptl_absorpt_coefficient_mu    3.854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       sheet
_exptl_crystal_F_000             696
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.080
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.4584
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 1947 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.014(14)
_refine_ls_extinction_coef       0.0056(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5247
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0519
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0840P)^2^+0.5010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1461
_refine_ls_wR_factor_ref         0.1493
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                4945
_reflns_number_total             5247
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ob01246a2.cif
_cod_data_source_block           cu_160121a
_cod_depositor_comments          'Adding full bibliography for 7155182.cif.'
_cod_database_code               7155182
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.249
_shelx_estimated_absorpt_t_max   0.748
_shelx_res_checksum              2637