Palladium-Catalyzed Diastereoselective Synthesis of 3-Arylbutanoic Acid Derivatives.
Zhi, Wubin; Li, Jingya; Zou, Dapeng; Wu, Yusheng; Wu, Yangjie; The Journal of organic chemistry 82 (2017) 12286–12293; doi:10.1021/acs.joc.7b02104

data_4033036
_publ_section_title
;
 Palladium-Catalyzed Diastereoselective Synthesis of 3-Arylbutanoic Acid
 Derivatives.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12286
_journal_page_last               12293
_journal_paper_doi               10.1021/acs.joc.7b02104
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H22 N2 O3'
_chemical_formula_sum            'C18 H22 N2 O3'
_chemical_formula_weight         314.37
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-15
_audit_creation_method
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Olex2 1.2
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                90
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_cell_formula_units_Z            2
_cell_length_a                   7.2555(4)
_cell_length_b                   6.3055(4)
_cell_length_c                   19.0027(10)
_cell_measurement_reflns_used    2281
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.4960
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_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)'
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;
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omega____ theta____ kappa____ phi______ frames
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  2 omega  -47.00  -22.00   1.0000    1.0000
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  3 omega   34.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega   19.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega    4.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   59.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   19.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   58.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   -8.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   24.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 26

 11 omega   58.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 52

 12 omega  -27.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000 -180.0000 74

 13 omega   62.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega   39.00   73.00   1.0000    1.0000
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 15 omega   -3.00   33.00   1.0000    1.0000
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 16 omega   11.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   20.00   47.00   1.0000    1.0000
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 18 omega    2.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   64.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   27.00   61.00   1.0000    1.0000
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 21 omega   80.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 22 omega   89.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 23 omega   68.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   30.0000 31

 24 omega   80.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 27

 25 omega   89.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   90.0000 32

 26 omega   83.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   90.0000 72

 27 omega   89.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 28 omega   80.00  105.00   1.0000    1.5000
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    -      108.0000   77.0000    0.0000 25

 29 omega   40.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 55

 30 omega   85.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 33

 31 omega   79.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 27

 32 omega   89.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 25

 33 omega   79.00  105.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

 34 omega   39.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

 35 omega   88.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 29

 36 omega   91.00  144.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 53

 37 omega  118.00  146.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 28

 38 omega  118.00  145.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 27

 39 omega   86.00  118.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 40 omega   80.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 27

 41 omega  125.00  166.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   60.0000 41

 42 omega   89.00  115.00   1.0000    1.5000
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    -      108.0000   61.0000   60.0000 26

 43 omega  119.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 56

 44 omega   62.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 45 omega   81.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
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 46 omega   89.00  167.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 78

 47 omega   89.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 25

 48 omega   88.00  114.00   1.0000    1.5000
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 49 omega   80.00  105.00   1.0000    1.5000
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 50 omega   92.00  119.00   1.0000    1.5000
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 51 omega  144.00  170.00   1.0000    1.5000
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 52 omega  128.00  171.00   1.0000    1.5000
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 53 omega   63.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 29
;
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_diffrn_orient_matrix_UB_11      -0.2129811000
_diffrn_orient_matrix_UB_12      -0.0214595000
_diffrn_orient_matrix_UB_13      -0.0069389000
_diffrn_orient_matrix_UB_21      -0.0076712000
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_diffrn_orient_matrix_UB_33      -0.0002850000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
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_diffrn_reflns_number            7018
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_diffrn_reflns_theta_full        67.078
_diffrn_reflns_theta_max         67.078
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93436
_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.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.152
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_refine_ls_abs_structure_details
;
 Flack x determined using 875 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(16)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2716
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0550P)^2^+0.0328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0942
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_reflns_Friedel_fraction_full    0.729
_reflns_Friedel_fraction_max     0.729
_reflns_number_gt                2504
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02104_si_002.cif
_cod_data_source_block           201611172
_cod_depositor_comments          'Adding full bibliography for 4033036.cif.'
_cod_original_cell_volume        863.06(8)
_cod_database_code               4033036
_chemical_oxdiff_formula         C20H20N4O2
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. 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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              77850
_shelx_hkl_checksum              86176
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'