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_4130315
_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         'C11 H12 O2'
_chemical_formula_sum            'C11 H12 O2'
_chemical_formula_weight         176.21
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-26
_audit_creation_method
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Olex2 1.2-beta
(compiled 2016.02.16 svn.r3264 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7621(2)
_cell_length_b                   8.4156(4)
_cell_length_c                   22.4052(12)
_cell_measurement_reflns_used    2686
_cell_measurement_temperature    181(2)
_cell_measurement_theta_max      72.7720
_cell_measurement_theta_min      5.5870
_cell_volume                     897.91(7)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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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)'
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_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      181(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4679
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    8.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.8115   38.0000   60.0000 110

  2 omega  102.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000  -60.0000 66

  3 omega  111.00  138.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  111.0000 -180.0000 27

  4 omega   77.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -60.0000 68

  5 omega   90.00  147.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000 -150.0000 57

  6 omega   82.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000  -90.0000 27

  7 omega   53.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000 -150.0000 55

  8 omega   37.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000 -150.0000 48

  9 omega   36.00  129.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -61.0000 -120.0000 93

 10 omega   24.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -94.0000   90.0000 85

 11 omega   47.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499  -30.0000  120.0000 92

 12 omega   32.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   15.0000  120.0000 132

 13 omega   85.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.8115  178.0000   60.0000 27

 14 omega  -24.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.8115  -38.0000 -120.0000 77

 15 omega    1.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       38.8115  -99.0000   60.0000 73

 16 omega -112.00  -85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.8115  -99.0000 -150.0000 27

 17 omega -109.00  -82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.8115  -99.0000  -90.0000 27

 18 omega -113.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.8115  -57.0000 -150.0000 104
;
_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      -0.0142921000
_diffrn_orient_matrix_UB_12      -0.0863782000
_diffrn_orient_matrix_UB_13      0.0605547000
_diffrn_orient_matrix_UB_21      0.2857126000
_diffrn_orient_matrix_UB_22      -0.0784316000
_diffrn_orient_matrix_UB_23      -0.0127067000
_diffrn_orient_matrix_UB_31      0.1510822000
_diffrn_orient_matrix_UB_32      0.1408930000
_diffrn_orient_matrix_UB_33      0.0301029000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         72.896
_diffrn_reflns_theta_min         3.946
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   analytical
_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)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.303
_exptl_crystal_description       irregular
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.6694
_exptl_crystal_size_mid          0.2407
_exptl_crystal_size_min          0.0855
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
Hooft -0.03(15)
Flack (Parson) -0.19(15)
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0789P)^2^+0.0802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.650
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_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1676
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02158_si_003.cif
_cod_data_source_block           gb905
_cod_original_cell_volume        897.91(8)
_cod_database_code               4130315
_chemical_oxdiff_formula         'C11 H12 O2'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.2(4) -0.2(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C11(H11), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C5(H5)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'