Palladium-Catalyzed Enantioselective Intermolecular Carboetherification of Dihydrofurans.
Borrajo-Calleja, Gustavo M; Bizet, Vincent; Mazet, Clément; Journal of the American Chemical Society 138 (2016) 4014–4017; doi:10.1021/jacs.6b02158

data_4130314
_publ_section_title
;
 Palladium-Catalyzed Enantioselective Intermolecular Carboetherification
 of Dihydrofurans.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4014
_journal_page_last               4017
_journal_paper_doi               10.1021/jacs.6b02158
_journal_volume                  138
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H8 F2 O2'
_chemical_formula_sum            'C10 H8 F2 O2'
_chemical_formula_weight         198.16
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                71.243(16)
_cell_angle_beta                 75.321(16)
_cell_angle_gamma                76.523(18)
_cell_formula_units_Z            2
_cell_length_a                   5.4814(12)
_cell_length_b                   8.5363(17)
_cell_length_c                   10.1397(17)
_cell_measurement_reflns_used    4838
_cell_measurement_temperature    180.1(2)
_cell_measurement_theta_max      76.2660
_cell_measurement_theta_min      8.4730
_cell_volume                     428.59(15)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -12.00   34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega   -4.00   21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   80.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  -30.0000 98

  4 omega  132.00  159.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000 -150.0000 27

  5 omega  112.00  150.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  -60.0000 38

  6 omega  108.00  135.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000    0.0000 27

  7 omega  115.00  153.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000   30.0000 38

  8 omega  109.00  136.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   60.0000 27

  9 omega  124.00  151.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000  120.0000 27

 10 omega  114.00  177.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  150.0000 63

 11 omega  100.00  171.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  111.0000   60.0000 71

 12 omega   85.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000   60.0000 26

 13 omega   85.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000   30.0000 27

 14 omega   85.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000    0.0000 26

 15 omega   83.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000    0.0000 26

 16 omega   83.00  144.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000   30.0000 61

 17 omega   85.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000  120.0000 26

 18 omega   83.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000  150.0000 26

 19 omega   83.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000  120.0000 26

 20 omega   85.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000  150.0000 26

 21 omega   80.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  120.0000 98

 22 omega   86.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000  -60.0000 25

 23 omega   83.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000  -30.0000 28

 24 omega   87.00  114.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000 -150.0000 27

 25 omega   83.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000 -180.0000 28

 26 omega   85.00  111.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   45.0000 -180.0000 26

 27 omega   80.00  162.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -120.0000 82

 28 omega   83.00  110.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000 -150.0000 27

 29 omega   83.00  147.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000 -120.0000 64

 30 omega   80.00  177.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  -90.0000 97

 31 omega   83.00  112.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000   60.0000 29

 32 omega   80.00  175.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   30.0000 95

 33 omega   83.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000   90.0000 26

 34 omega   80.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  150.0000 26

 35 omega   80.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   90.0000 26

 36 omega   80.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000   60.0000 26

 37 omega   80.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000    0.0000 26

 38 omega   80.00  106.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000  -60.0000 26

 39 omega   83.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000  -60.0000 26

 40 omega   83.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   61.0000  -90.0000 26

 41 omega   80.00  110.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -150.0000 30

 42 omega   80.00  176.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   77.0000 -180.0000 96

 43 omega   29.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -94.0000 -120.0000 80

 44 omega   89.00  130.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       38.9365 -178.0000  -90.0000 41

 45 omega   67.00  124.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -129.0000   71.2439 57

 46 omega   40.00  114.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000 -111.0000  150.0000 74

 47 omega   29.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -94.0000   90.0000 55

 48 omega   29.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -94.0000  -30.0000 62

 49 omega   29.00  103.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000  -94.0000 -180.0000 74

 50 omega   78.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      116.0000   30.0000  120.0000 26

 51 omega  -41.00   -3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -77.0000   60.0000 38

 52 omega  -59.00   -6.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -77.0000  -60.0000 53

 53 omega  -67.00   -6.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000    0.0000 61

 54 omega  -60.00   -6.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000   90.0000 54

 55 omega  -70.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365   38.0000  150.0000 105

 56 omega  -65.00  -38.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365   57.0000   30.0000 27

 57 omega -117.00  -71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000    0.0000 46

 58 omega  -95.00  -34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  178.0000 -180.0000 61

 59 omega -130.00  -48.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  178.0000  -90.0000 82

 60 omega -130.00  -48.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  178.0000   90.0000 82

 61 omega -106.00   -7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000 -120.0000 99

 62 omega -103.00  -75.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -77.0000  -60.0000 28

 63 omega -123.00  -48.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -77.0000   60.0000 75

 64 omega -102.00  -62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -57.0000   90.0000 40

 65 omega -123.00   -4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  -77.0000 -180.0000 119

 66 omega  -63.00  -38.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.9365  109.0000   43.0000 25

 67 omega    9.00   34.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   86.0000  171.2039 25

 68 omega   19.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000   64.2202 25

 69 omega   19.00   44.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000  -74.8491 25

 70 omega   19.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   82.0000  -49.8976 26

 71 omega   32.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   59.8029 35

 72 omega   32.00   60.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -165.0388 28

 73 omega   32.00   73.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000    9.1042 41

 74 omega   33.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   76.0000 -128.4477 29

 75 omega   33.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000  140.6993 34

 76 omega   36.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  110.5334 47

 77 omega   36.00   70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       72.0000   77.0000  -66.4022 34

 78 omega   49.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   73.0000  -32.4497 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0423326000
_diffrn_orient_matrix_UB_12      -0.1926148000
_diffrn_orient_matrix_UB_13      0.0352093000
_diffrn_orient_matrix_UB_21      0.2195688000
_diffrn_orient_matrix_UB_22      -0.0127768000
_diffrn_orient_matrix_UB_23      0.0746189000
_diffrn_orient_matrix_UB_31      -0.1925543000
_diffrn_orient_matrix_UB_32      -0.0076628000
_diffrn_orient_matrix_UB_33      0.1413242000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_unetI/netI     0.0053
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3423
_diffrn_reflns_point_group_measured_fraction_full 0.773
_diffrn_reflns_point_group_measured_fraction_max 0.755
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         76.204
_diffrn_reflns_theta_min         4.695
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       plate
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.6143
_exptl_crystal_size_mid          0.2488
_exptl_crystal_size_min          0.1202
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
Non-merohedral 
twinned data. The flack parameter was refined on
each individual twin component.
;
_refine_ls_abs_structure_Flack   -0.03(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0865P)^2^+0.0434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.523
_reflns_Friedel_fraction_full    0.546
_reflns_Friedel_fraction_max     0.519
_reflns_number_gt                3359
_reflns_number_total             3423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02158_si_004.cif
_cod_data_source_block           gb930
_cod_original_cell_volume        428.59(16)
_cod_database_code               4130314
_chemical_oxdiff_formula         'C10 F2 O2 H8'
_diffrn_oxdiff_twin_integration_method simultaneous
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5380(16) 0.4620(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C30(H30), C34(H34), C14(H14), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C12(H12A,H12B), C32(H32A,H32B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C28(H28), C25(H25), C5(H5)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'