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_4130316
_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         'C18 H18 O2'
_chemical_formula_sum            'C18 H18 O2'
_chemical_formula_weight         266.32
_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
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_cell_measurement_temperature    180.00(14)
_cell_measurement_theta_max      73.3260
_cell_measurement_theta_min      4.1280
_cell_volume                     1409.477(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)
;
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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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;
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omega____ theta____ kappa____ phi______ frames
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  2 omega  -16.00   10.00   1.0000    1.0000
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  3 omega  -60.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega   48.00  107.00   1.0000    1.0000
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  5 omega   36.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega  117.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega  115.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega  148.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega -111.00  -85.00   1.0000    1.0000
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 10 omega  -60.00    2.00   1.0000    1.0000
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 11 omega  102.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   67.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 13 omega  142.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega  108.00  164.00   1.0000    1.0000
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 15 omega  -37.00   -5.00   1.0000    1.0000
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 16 omega  -99.00  -61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega  -46.00   -5.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega  -68.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega -115.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   56.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega  101.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 22 omega    4.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 23 omega    4.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 24 omega   13.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 25 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 26 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 27 omega   97.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 28 omega   27.00   68.00   1.0000    1.0000
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 29 omega   93.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 30 omega   28.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 31 omega   92.00  118.00   1.0000    1.0000
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 32 omega   29.00  108.00   1.0000    1.0000
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 33 omega   36.00   62.00   1.0000    1.0000
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 34 omega   30.00   63.00   1.0000    1.0000
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 35 omega   28.00   64.00   1.0000    1.0000
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 36 omega   37.00   89.00   1.0000    1.0000
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 37 omega   36.00   62.00   1.0000    1.0000
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 38 omega   62.00  101.00   1.0000    1.0000
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 39 omega   75.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 40 omega   74.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 41 omega  127.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 42 omega   74.00  119.00   1.0000    1.0000
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 43 omega   78.00  160.00   1.0000    1.0000
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 44 omega   78.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 45 omega  123.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 46 omega   77.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 47 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000  -90.0000 26

 48 omega   43.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 49 omega   74.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 50 omega   77.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 51 omega  118.00  144.00   1.0000    1.0000
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 52 omega  121.00  150.00   1.0000    1.0000
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 53 omega   74.00  100.00   1.0000    1.0000
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 54 omega   77.00  117.00   1.0000    1.0000
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 55 omega   77.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 56 omega   77.00  103.00   1.0000    1.0000
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 57 omega   59.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 58 omega   38.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 59 omega   76.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 60 omega   78.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 61 omega   74.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -30.0000 27

 62 omega   78.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 63 omega   75.00  174.00   1.0000    1.0000
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 64 omega   19.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 65 omega -129.00   54.00   1.0000    1.0000
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 66 omega -129.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 67 omega -129.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 68 omega -129.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615    0.0000  -60.0000 183

 69 omega -129.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 70 omega -129.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 71 omega -129.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.5615    0.0000  -90.0000 183

 72 omega    1.00  122.00   1.0000    1.0000
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    -       37.5615   77.0000 -180.0000 121

 73 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000    0.0000 183

 74 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000  -30.0000 183

 75 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000  -60.0000 183

 76 omega   57.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615  178.0000 -150.0000 73

 77 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000   60.0000 183

 78 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000   30.0000 183

 79 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000  -90.0000 183

 80 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000 -120.0000 183

 81 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000  150.0000 183

 82 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000  120.0000 183

 83 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000 -150.0000 183

 84 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000   90.0000 183

 85 omega  -54.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5615    0.0000 -180.0000 183

 86 omega   10.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   84.0000   81.4819 28

 87 omega   10.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   85.0000  -82.4542 26

 88 omega   15.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000 -104.1869 31

 89 omega   19.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   80.0000 -161.5918 27

 90 omega   28.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   75.0000  -26.9986 119

 91 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000   30.0000 104

 92 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  120.0000 104

 93 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000    0.0000 104

 94 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   61.0000 -150.0000 101

 95 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   77.0000  -60.0000 104

 96 omega   79.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      109.7499   45.0000 -180.0000 99
;
_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      0.0794547000
_diffrn_orient_matrix_UB_12      -0.1103396000
_diffrn_orient_matrix_UB_13      -0.0483401000
_diffrn_orient_matrix_UB_21      -0.1053507000
_diffrn_orient_matrix_UB_22      -0.1292801000
_diffrn_orient_matrix_UB_23      0.0308465000
_diffrn_orient_matrix_UB_31      -0.1598319000
_diffrn_orient_matrix_UB_32      0.0303661000
_diffrn_orient_matrix_UB_33      -0.0443445000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0099
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            48986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.421
_diffrn_reflns_theta_min         4.160
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.857
_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    1.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3332
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.1017
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
Hooft -0.06(4) using the student distribution
Pots-refinement Flack using the Parsons'method : -0.06(4), 1133 pairs

;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0055(5)
_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   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0315P)^2^+0.1928P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0646
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2753
_reflns_number_total             2831
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b02158_si_005.cif
_cod_data_source_block           vb415
_cod_original_cell_volume        1409.478(15)
_cod_database_code               4130316
_chemical_oxdiff_formula         'C18 H18 O2'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.1(2) -0.1(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C13(H13), C2(H2), C10(H10), C11(H11)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C15(H15), C6(H6), C20(H20), C19(H19), C16(H16), C7(H7)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C18(H18A,H18B,H18C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'