Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones.
Liang, Yufan; Fu, Gregory C.; Journal of the American Chemical Society 136 (2014) 5520–5524; doi:10.1021/ja501815p

data_4121570
_publ_section_title
;
 Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi
 Cross-Couplings of Racemic \a,\a-Dihaloketones.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5520
_journal_page_last               5524
_journal_paper_doi               10.1021/ja501815p
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H17 F O'
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_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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
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  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
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_cell_length_c                   17.2167(12)
_cell_measurement_reflns_used    44603
_cell_measurement_temperature    93
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_computing_cell_refinement
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CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
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_computing_data_collection
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CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
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CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
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SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
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_diffrn_ambient_temperature      93
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_diffrn_measured_fraction_theta_max 1.000
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AFC11 (Left): Eulerian 3 circle
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Rigaku Saturn944+ (2x2 bin mode)
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_diffrn_measurement_method       'profile data from \w-scans'
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_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
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_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_source                   'Rotating Anode'
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2009)'
_exptl_crystal_colour            colourless
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_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       Needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1128 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0224P)^2^+0.3900P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
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_reflns_number_gt                2761
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja501815p_si_001.cif
_cod_data_source_block           yfl01
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/rss-feeds/ACS/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 

 Adding full bibliography for 4121570--4121574.cif.
;
_cod_original_formula_sum        'C21 H17 F1 O1 '
_cod_database_code               4121570
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_shelxl_version_number           2013-2