Enantioselective Iron-Catalyzed Azidation of β-Keto Esters and Oxindoles
Qing-Hai Deng; Tim Bleith; Hubert Wadepohl; Lutz H. Gade; Journal of the American Chemical Society 135 (2013) 5356–5359; doi:10.1021/ja402082p

data_4119572
_publ_section_title
;
 Enantioselective Iron-Catalyzed Azidation of \b-Keto Esters and Oxindoles
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5356
_journal_page_last               5359
_journal_paper_doi               10.1021/ja402082p
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H14 Br F N4 O'
_chemical_formula_weight         449.28
_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_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_qd15a
_audit_creation_date
;
'Thu Feb 21 10:59:54 2013'
;
_audit_creation_method           SHELXL-2012
_audit_update_record             'Thu Feb 21 11:08:59 CET 2013'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1115(4)
_cell_length_b                   12.3278(3)
_cell_length_c                   12.5525(4)
_cell_measurement_reflns_used    45985
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      70.7590
_cell_measurement_theta_min      5.0080
_cell_volume                     1874.19(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_publication_material
'encif (Wadepohl, 2012); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SIR2011 (Giacovazzo et al., 2011)'
_diffrn_ambient_temperature      110(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
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omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 27

  2 omega  -71.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000   30.0000 41

  3 omega  -19.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000   30.0000 28

  4 omega  -26.00   44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   64.0000  150.0000 70

  5 omega  -21.00   24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega  -73.00  -24.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   21.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega  -28.00   18.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   38.0000  -90.0000 46

  9 omega  -13.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0000   80.0000  -30.1613 32

 10 omega    5.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000   80.0000  -87.7503 27

 11 omega    7.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   79.0000  -21.8381 25

 12 omega    7.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   78.0000 -150.6635 25

 13 omega   13.00   38.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   80.0000   19.6620 25

 14 omega   11.00   41.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   79.0000   59.4079 30

 15 omega   13.00   40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   77.0000 -114.3579 27

 16 omega   19.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   77.0000   -6.4953 27

 17 omega   15.00   40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega   15.00   40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   15.00   40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000  -49.9247 25

 20 omega   74.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   77.0000  174.7335 42

 21 omega   77.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   77.0000   -6.4953 27

 22 omega   26.00   54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   77.0000  174.7335 28

 23 omega   22.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   76.0000 -126.9441 25

 24 omega   19.00   44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  159.2140 25

 25 omega   20.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000  -47.1129 27

 26 omega   18.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000  138.7535 25

 27 omega   18.00   43.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000   59.5734 25

 28 omega   21.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 29 omega  -14.00   20.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -78.0000  -65.4761 34

 30 omega   31.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -150.1460 25

 31 omega   29.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000    0.7305 28

 32 omega   30.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   29.4815 25

 33 omega   34.00   61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   68.0000  -49.4071 27

 34 omega   31.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000  157.0166 27

 35 omega   83.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -125.1973 39

 36 omega   31.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  -99.9588 25

 37 omega   29.00   54.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -125.1973 25

 38 omega   30.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000   65.8120 27

 39 omega   34.00   59.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  -13.6343 25

 40 omega   43.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   66.0000  110.2529 39

 41 omega  105.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   66.0000 -164.5698 25

 42 omega   47.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   66.0000 -164.5698 27

 43 omega   78.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000 -101.9548 49

 44 omega   50.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   55.0000  137.6042 27

 45 omega   37.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  -54.0614 26

 46 omega   38.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000 -101.9548 34

 47 omega   36.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000  -80.0000 -149.3906 39

 48 omega   36.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  161.5175 28

 49 omega   42.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000 -110.2555 25

 50 omega   42.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000  -47.6907 25

 51 omega   44.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   73.0000    1.0921 95

 52 omega   51.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   61.0000  152.0544 27

 53 omega   47.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   65.0000   50.7364 44

 54 omega   -1.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000  -80.0000  136.8113 102

 55 omega   88.00  125.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   56.0000  154.5598 37

 56 omega   53.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   56.0000  154.5598 30

 57 omega   52.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000  -38.2049 55

 58 omega    5.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000  -80.0000   -2.9865 87

 59 omega   51.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000  -80.0000   66.7540 27

 60 omega   55.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   67.0000 -105.5467 90

 61 omega   52.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   73.0000  -58.9071 27

 62 omega   49.00  147.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   75.0000   72.8454 98

 63 omega   56.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   61.0000  -70.3393 30

 64 omega   59.00   86.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   64.0000 -150.1170 27

 65 omega   53.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   77.0000 -144.4864 26

 66 omega   53.00   87.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   75.0000   38.6263 34

 67 omega   55.00   83.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   72.0000  174.6646 28

 68 omega   63.00   93.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   46.0000  143.9900 30

 69 omega   58.00  119.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   73.0000  142.3444 61

 70 omega   59.00   86.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000  -79.0000 -173.2585 27

 71 omega   16.00  117.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000  -80.0000  -52.1611 101

 72 omega   63.00   90.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   77.0000 -160.0885 27

 73 omega   67.00   93.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   73.0000  -71.3013 26

 74 omega   71.00  137.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   69.0000  -34.7080 66

 75 omega   72.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   49.0000 -154.3223 27

 76 omega   70.00   96.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   69.0000  -53.9897 26

 77 omega   68.00  128.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   77.0000   41.0985 60

 78 omega   76.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   72.0000 -103.8432 82

 79 omega   80.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   61.0000    6.1964 26

 80 omega   84.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000 -140.1467 27

 81 omega   37.00  139.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  103.1066 102

 82 omega   81.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 27

 83 omega   39.00  138.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  -95.0624 99

 84 omega  110.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 44

 85 omega   78.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 27

 86 omega   84.00  123.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  120.0000 39

 87 omega   85.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -30.0000 90

 88 omega   86.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -90.0000 88

 89 omega   73.00  100.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 27

 90 omega   87.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 27

 91 omega   85.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   30.0000 90

 92 omega  148.00  173.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 25

 93 omega   79.00  104.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 25

 94 omega  140.00  172.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 32

 95 omega   79.00  139.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 60

 96 omega   79.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 98

 97 omega  143.00  170.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 27

 98 omega   81.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 27

 99 omega  120.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 58

100 omega   78.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 27

101 omega   78.00  169.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 91

102 omega   86.00  113.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  150.0000 27

103 omega   85.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -120.0000 26

104 omega   78.00  165.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 87

105 omega   85.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 89

106 omega   84.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   70.0000   55.0000 37

107 omega   78.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 27

108 omega   78.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 100

109 omega   78.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 100

110 omega   85.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   90.0000 26

111 omega   75.00  102.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000    1.3705 27

112 omega   43.00   73.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -79.0000    1.3705 30

113 omega  152.00  177.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000  -68.7912 25

114 omega   80.00  106.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000  -68.7912 26

115 omega   84.00  119.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  -21.8789 35

116 omega   45.00  123.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -78.0000 -173.0789 78

117 omega  -73.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000  -30.0000 117

118 omega  -29.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       -3.5000   38.0000 -150.0000 98

119 omega  -13.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0000   79.0000  138.7943 60

120 omega    7.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   78.0000 -150.6635 42

121 omega    7.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   78.0000  -65.5664 42

122 omega    7.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   78.0000   59.7582 42

123 omega   15.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000  -49.9247 32

124 omega   15.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   78.0000  -87.9401 34

125 omega   18.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000  138.7535 28

126 omega   19.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  159.2140 28

127 omega   21.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   76.0000 -126.9441 99

128 omega   18.00   46.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000   59.5734 28

129 omega  -16.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 100

130 omega   30.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   73.0000 -150.1460 97

131 omega   30.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  -99.9588 98

132 omega   29.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   29.4815 99

133 omega   29.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000   65.8120 99

134 omega   39.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   66.0000  110.2529 91

135 omega   33.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  -13.6343 99

136 omega   -5.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000  -80.0000 -149.3906 103

137 omega   36.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  161.5175 100

138 omega   37.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000 -101.9548 99

139 omega   47.00  138.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   65.0000   50.7364 91

140 omega   41.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000 -110.2555 99

141 omega   41.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000  -47.6907 99

142 omega   53.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   56.0000  154.5598 90

143 omega   49.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000  -38.2049 93

144 omega    3.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000  -80.0000   66.7540 103

145 omega    3.00  106.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000  -80.0000   -2.9865 103

146 omega   48.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   38.0000 -166.8351 98

147 omega   54.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   67.0000 -105.5467 92

148 omega   56.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   61.0000  -70.3393 90

149 omega   50.00  147.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   73.0000  -58.9071 97

150 omega   49.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   75.0000   72.8454 99

151 omega   52.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   36.0000  137.3428 98

152 omega   57.00  147.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   56.0000 -133.9558 90

153 omega   53.00  152.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   75.0000   38.6263 99

154 omega   58.00  155.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   73.0000  142.3444 97

155 omega   60.00  160.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   77.0000 -160.0885 100

156 omega   38.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -78.0000 -173.0789 25

157 omega   78.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 100

158 omega   78.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 100

159 omega   85.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -90.0000 90

160 omega   78.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 100

161 omega   78.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 100

162 omega   37.00  140.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  -95.0624 103

163 omega   41.00  131.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -64.0000   30.0000 90

164 omega   86.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -180.0000 92

165 omega   74.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 104

166 omega   74.00  178.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -90.0000 104

167 omega   85.00  175.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 90

168 omega   38.00  138.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 100

169 omega   35.00   94.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 59

170 omega   35.00   94.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 59

171 omega   35.00   94.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 59

172 omega   35.00   94.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 59

173 omega   35.00   94.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 59

;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      0.0800927000
_diffrn_orient_matrix_UB_12      0.0028687000
_diffrn_orient_matrix_UB_13      0.0952863000
_diffrn_orient_matrix_UB_21      0.0259181000
_diffrn_orient_matrix_UB_22      -0.1208806000
_diffrn_orient_matrix_UB_23      -0.0180576000
_diffrn_orient_matrix_UB_31      0.0954851000
_diffrn_orient_matrix_UB_32      0.0316219000
_diffrn_orient_matrix_UB_33      -0.0750442000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0825
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            80965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.322
_diffrn_reflns_theta_min         5.028
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    3.261
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.1501
_exptl_crystal_size_mid          0.1307
_exptl_crystal_size_min          0.0894
_refine_diff_density_max         0.863
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.026(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0217P)^2^+2.4192P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.744
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3597
_reflns_number_total             3611
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja402082p_si_001_3.cif
_cod_data_source_block           ga_qd15a
_cod_original_cell_volume        1874.20(10)
_cod_database_code               4119572
_audit_block_refno               1779
_audit_block_usercomment         'd8-95 colourless plate'
_shelx_estimated_absorpt_t_min   0.736
_shelx_estimated_absorpt_t_max   0.736
_shelxl_version_number           2012-6
_shelx_res_checksum              88150
_cell_oxdiff_length_a            12.10263(15)
_cell_oxdiff_length_b            12.32687(13)
_cell_oxdiff_length_c            12.56325(15)
_cell_oxdiff_angle_alpha         90.3108(9)
_cell_oxdiff_angle_beta          89.9908(10)
_cell_oxdiff_angle_gamma         90.4185(9)
_cell_oxdiff_volume              1874.20(4)
_cell_oxdiff_measurement_reflns_used 45985
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1