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_4119571
_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 H19 Br2 N3 O3'
_chemical_formula_weight         533.22
_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_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_qd14
_audit_creation_date
;
'Mon Feb 11 10:55:59 2013'
;
_audit_creation_method           SHELXL-2012
_audit_update_record             'Mon Feb 11 14:20:43 CET 2013'
_cell_angle_alpha                90
_cell_angle_beta                 98.8603(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.82402(8)
_cell_length_b                   22.0575(4)
_cell_length_c                   8.42973(12)
_cell_measurement_reflns_used    26943
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      71.6770
_cell_measurement_theta_min      5.2900
_cell_volume                     1069.99(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_publication_material
'encif (Wadepohl, 2012); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_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 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
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omega____ theta____ kappa____ phi______ frames
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  2 omega  -20.00    7.00   1.0000    5.0000
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  3 omega  -13.00   14.00   1.0000    5.0000
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  4 omega  -40.00  -12.00   1.0000   10.0000
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  5 omega  -39.00  -14.00   1.0000   10.0000
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  6 omega  -47.00   29.00   1.0000   10.0000
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  7 omega  -47.00   30.00   1.0000   10.0000
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  8 omega  -45.00  -12.00   1.0000   10.0000
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  9 omega  -50.00  -15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 35

 10 omega  -39.00  -12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega -112.00  -72.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 40

 12 omega  -39.00  -12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 13 omega  -40.00  -13.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  150.0000 27

 14 omega  -39.00  -12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 27

 15 omega   15.00   40.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000   62.7743 25

 16 omega   15.00   40.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   19.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega   19.00   44.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   22.00   51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   74.0000   17.0893 29

 20 omega   25.00   58.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000  122.2919 33

 21 omega   23.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  -94.5906 26

 22 omega   23.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   52.3128 25

 23 omega   23.00   48.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -104.2069 25

 24 omega   26.00   53.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1171   77.0000 -120.0000 27

 25 omega  -16.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1171  -80.0000  -41.0396 102

 26 omega  102.00  128.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 27 omega   29.00   56.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 28 omega   37.00   64.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 29 omega   29.00   62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 30 omega  103.00  128.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   41.6094 25

 31 omega   44.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   41.6094 27

 32 omega   36.00   65.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000 -127.2419 29

 33 omega   34.00   63.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  -65.7769 29

 34 omega   46.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 35 omega   43.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   67.0000  -19.9571 41

 36 omega   90.00  117.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   63.0000   78.5967 27

 37 omega   62.00   89.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   61.0000 -106.4973 27

 38 omega   44.00   71.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   63.0000   78.5967 27

 39 omega   42.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   74.0000  127.4235 31

 40 omega   45.00  138.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   70.0000  171.6728 93

 41 omega   51.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   57.0000  104.7481 58

 42 omega   47.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   66.0000 -127.2530 31

 43 omega   54.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   48.0000    7.0367 28

 44 omega    4.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000  -80.0000   79.6371 101

 45 omega   52.00  101.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   65.0000  -90.3106 49

 46 omega   56.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   56.0000  -53.6881 27

 47 omega   45.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  147.3011 70

 48 omega   45.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 49 omega  110.00  137.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 50 omega   51.00   87.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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 51 omega   35.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000  -80.0000 -152.5418 58

 52 omega   62.00  150.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   59.0000  -54.8339 88

 53 omega   64.00  108.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   50.0000   21.3209 44

 54 omega   74.00  102.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   52.0000  120.6238 28

 55 omega   44.00  121.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -79.0000  121.0476 77

 56 omega   80.00  175.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000 -180.0000 95

 57 omega  112.00  176.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -30.0000 64

 58 omega   80.00  107.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -30.0000 27

 59 omega  138.00  168.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000   30.0000 30

 60 omega   89.00  114.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000   30.0000 25

 61 omega   80.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  150.0000 26

 62 omega   81.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -60.0000 25

 63 omega  131.00  158.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -90.0000 27

 64 omega   81.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -90.0000 25

 65 omega  117.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000    0.0000 61

 66 omega   80.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000    0.0000 26

 67 omega   98.00  143.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000   90.0000 45

 68 omega  135.00  177.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000 -150.0000 42

 69 omega   80.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000 -150.0000 26

 70 omega   96.00  147.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000  -60.0000 51

 71 omega   80.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  120.0000 26

 72 omega   89.00  117.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  -90.0000 28

 73 omega   85.00  124.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000  -30.0000 39

 74 omega   97.00  154.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000   60.0000 57

 75 omega   64.00  100.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -79.0000   66.0709 36

 76 omega   85.00  112.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000   60.0000 27

 77 omega   85.00  112.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000   30.0000 27

 78 omega   85.00  116.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000    0.0000 31

 79 omega   86.00  139.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000 -120.0000 53

 80 omega   89.00  174.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  120.0000 85

 81 omega   89.00  125.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  -30.0000 36

 82 omega  123.00  175.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  -60.0000 52

 83 omega   89.00  117.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  -60.0000 28

 84 omega   39.00  137.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000 -104.9906 98

 85 omega   86.00  131.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000   90.0000 45

 86 omega   43.00   96.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -77.0000   30.0000 53

 87 omega   80.00  107.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000   60.0000 27

 88 omega   61.00  104.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000  -32.1034 43

 89 omega   81.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000   30.0000 25

 90 omega   90.00  176.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  150.0000 86

 91 omega   89.00  175.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000   60.0000 86

 92 omega   98.00  125.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000  -30.0000 27

 93 omega   90.00  117.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000   30.0000 27

 94 omega   84.00  177.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000 -120.0000 93

 95 omega   73.00  100.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -78.0000  173.9967 27

 96 omega   41.00   69.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -78.0000  173.9967 28

 97 omega  122.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000   90.0000 56

 98 omega   81.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000   90.0000 25

 99 omega  -26.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  150.0000 98

100 omega  -30.00   70.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -90.0000 100

101 omega -113.00  -12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 101

102 omega -116.00   30.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   -6.0000   48.0000 146

103 omega -113.00  -12.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   30.0000 101

104 omega -111.00  -21.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -90.0000 90

105 omega -116.00   30.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   -6.0000   48.0000 146

106 omega   19.00   47.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  -59.7582 28

107 omega   22.00  120.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   74.0000   17.0893 98

108 omega   19.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  167.5277 30

109 omega   25.00  124.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000   97.5071 99

110 omega   23.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -104.2069 26

111 omega   23.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  -94.5906 26

112 omega   23.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   52.3128 26

113 omega  -14.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1171  -57.0000 -180.0000 91

114 omega  -15.00   86.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1171  -78.0000   82.3799 101

115 omega   34.00  124.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1171   57.0000  150.0000 90

116 omega   29.00  128.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  -54.0672 99

117 omega   28.00  128.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   87.8885 100

118 omega   44.00  134.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   63.0000   78.5967 90

119 omega   46.00  134.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   59.0000   29.6172 88

120 omega   42.00  134.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   67.0000  -19.9571 92

121 omega   -5.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000  -80.0000 -130.2830 103

122 omega   47.00  141.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
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123 omega   47.00  138.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   66.0000 -127.2530 91

124 omega   49.00  139.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   57.0000  104.7481 90

125 omega   42.00  140.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   74.0000  127.4235 98

126 omega   53.00  143.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   56.0000  -53.6881 90

127 omega   44.00  144.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  147.3011 100

128 omega   51.00  142.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   65.0000  -90.3106 91

129 omega   44.00  144.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000 -175.7981 100

130 omega   51.00  147.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   71.0000 -162.5775 96

131 omega   11.00  114.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000  -80.0000 -152.5418 103

132 omega   62.00  150.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   59.0000  -54.8339 88

133 omega   80.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  150.0000 98

134 omega   85.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000 -120.0000 93

135 omega   40.00  104.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -50.0000   90.0000 64

136 omega   37.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -25.0000  150.0000 57

137 omega   39.00  142.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000  -32.1034 103

138 omega   37.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -25.0000  -90.0000 57

139 omega   37.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -25.0000   30.0000 57

140 omega   40.00  116.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -77.0000   90.0000 76

141 omega   37.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -25.0000 -150.0000 57

;
_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      -0.0782348000
_diffrn_orient_matrix_UB_12      -0.0036965000
_diffrn_orient_matrix_UB_13      -0.1828412000
_diffrn_orient_matrix_UB_21      0.2558313000
_diffrn_orient_matrix_UB_22      -0.0038120000
_diffrn_orient_matrix_UB_23      -0.0256337000
_diffrn_orient_matrix_UB_31      -0.0097631000
_diffrn_orient_matrix_UB_32      -0.0696453000
_diffrn_orient_matrix_UB_33      0.0110949000
_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  0.0514
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            36574
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.969
_diffrn_reflns_theta_min         4.008
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    5.051
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
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)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       needle
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.1991
_exptl_crystal_size_mid          0.0555
_exptl_crystal_size_min          0.0206
_refine_diff_density_max         0.951
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1713 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.016(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0255
_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^)+(0.0396P)^2^+0.5929P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                3851
_reflns_number_total             3870
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja402082p_si_001_2.cif
_cod_data_source_block           ga_qd14
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4119571
_audit_block_refno               1697
_audit_block_usercomment         'd8-91 colorless needle'
_shelx_estimated_absorpt_t_min   0.632
_shelx_estimated_absorpt_t_max   0.632
_shelxl_version_number           2012-6
_shelx_res_checksum              1617
_cell_oxdiff_length_a            5.82443(7)
_cell_oxdiff_length_b            22.0562(3)
_cell_oxdiff_length_c            8.42997(10)
_cell_oxdiff_angle_alpha         90.0056(11)
_cell_oxdiff_angle_beta          98.8739(11)
_cell_oxdiff_angle_gamma         89.9805(12)
_cell_oxdiff_volume              1069.99(2)
_cell_oxdiff_measurement_reflns_used 26943
_reflns_odcompleteness_completeness 98.83
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1