Bis(diisopropylphosphinomethyl)amine Nickel(II) and Nickel(0) Complexes: Coordination Chemistry, Reactivity, and Catalytic Decarbonylative C‒H Arylation of Benzoxazole
Kruckenberg, Achim; Wadepohl, Hubert; Gade, Lutz H.; Organometallics 32 (2013) 5153–; doi:10.1021/om400711d

data_4081441
_publ_section_title
;
 Bis(diisopropylphosphinomethyl)amine Nickel(II) and Nickel(0) Complexes:
 Coordination Chemistry, Reactivity, and Catalytic Decarbonylative C--H
 Arylation of Benzoxazole
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              5153
_journal_paper_doi               10.1021/om400711d
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C21 H41 N Ni O P2'
_chemical_formula_sum            'C21 H41 N Ni O P2'
_chemical_formula_weight         444.20
_chemical_properties_physical    air-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ak51
_audit_creation_date
;
'Mon Feb 04 15:45:11 2013'
;
_audit_update_record             'Thu Jul  4 12:02:56 CEST 2013'
_cell_angle_alpha                90
_cell_angle_beta                 99.531(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.62335(17)
_cell_length_b                   16.8000(3)
_cell_length_c                   18.4072(4)
_cell_measurement_reflns_used    12958
_cell_measurement_temperature    110(1)
_cell_measurement_theta_max      71.2330
_cell_measurement_theta_min      4.8660
_cell_volume                     2324.91(8)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
'encif (Wadepohl, 2009-13); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_temperature      110(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9241
_diffrn_detector_type            'Agilent EOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
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  2 omega  -10.00   69.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega  -69.00  -14.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -13.00   23.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega    7.00   36.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega  -25.00    0.00   0.5000   20.0000
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  7 omega   15.00   43.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   10.00   35.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   80.0000 -175.9263 50

  9 omega  -50.00  -12.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega  -71.00   27.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega  -57.00  -12.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   90.0000 90

 12 omega  -68.00  -15.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -150.0000 106

 13 omega  -93.00  -61.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega  -72.00   27.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   77.0000   30.0000 198

 15 omega   17.00   44.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   78.0000  -12.4688 54

 16 omega   14.00   42.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   15.00   40.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega   23.00   50.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   15.00   40.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000  -48.9147 50

 20 omega   18.00   43.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000   40.6915 50

 21 omega   19.00   45.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  107.1348 52

 22 omega   19.00   44.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  142.7677 50

 23 omega   19.00   44.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  -47.5822 50

 24 omega   19.00   44.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000   62.8639 50

 25 omega   19.00   45.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  122.2224 52

 26 omega   18.00   43.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000 -177.6820 50

 27 omega   27.00   54.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000   67.2267 54

 28 omega   23.00   48.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  -88.3147 50

 29 omega   27.00   52.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   73.0000 -171.9377 50

 30 omega   28.00   55.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000  -12.9662 54

 31 omega   30.00   55.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -42.2901 50

 32 omega   30.00   57.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  -32.0250 54

 33 omega   29.00   55.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   13.9408 52

 34 omega   28.00   55.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -57.2827 54

 35 omega   30.00   69.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  132.4511 78

 36 omega   37.00   64.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   72.0000 -146.7317 54

 37 omega   30.00   57.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -69.7413 54

 38 omega   38.00   65.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   68.0000  167.6392 54

 39 omega   36.00   61.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   71.0000   35.0496 50

 40 omega   34.00   61.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -172.6726 54

 41 omega   69.00   94.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000  -80.0000  -75.1193 50

 42 omega   32.00   59.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  111.5765 54

 43 omega  105.00  130.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   68.0000  167.6392 50

 44 omega   36.00   63.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   79.6465 54

 45 omega   86.00  113.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000   79.6465 54

 46 omega   47.00   75.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   52.0000  169.2065 56

 47 omega   77.00  133.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   71.0000 -113.4972 112

 48 omega   39.00   70.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
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 49 omega   65.00   92.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   52.0000  152.4653 54

 50 omega   53.00   80.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   60.0000  174.5834 54

 51 omega    0.00  102.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000  -80.0000   75.4945 204

 52 omega   48.00  101.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   63.0000  -39.6891 106

 53 omega  113.00  140.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   76.0000   63.9292 54

 54 omega   41.00   68.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   76.0000   63.9292 54

 55 omega   40.00   67.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000 -117.6678 54

 56 omega   45.00   72.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   75.0000   13.2719 54

 57 omega  106.00  133.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  -33.4456 54

 58 omega   44.00   92.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000  -33.4456 96

 59 omega   45.00   71.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   75.0000 -173.2552 52

 60 omega   44.00   71.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   77.0000 -154.6068 54

 61 omega   49.00   92.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   69.0000  -84.4389 86

 62 omega   48.00   75.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   77.0000 -132.9010 54

 63 omega   57.00  111.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   71.0000   69.5958 108

 64 omega   56.00  133.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   66.0000   -0.8161 154

 65 omega   53.00  146.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   71.0000  110.5868 186

 66 omega   38.00   85.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000  -80.0000 -112.6767 94

 67 omega   73.00  100.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000  -78.0000  -23.4721 54

 68 omega   53.00   80.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   77.0000    7.9994 54

 69 omega   63.00   94.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   51.0000 -155.1783 62

 70 omega   59.00   86.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   64.0000 -152.0687 54

 71 omega   69.00  150.00   0.5000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   52.0000  -51.3909 162

 72 omega   67.00  115.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   52.0000 -179.9263 96

 73 omega   60.00  143.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   74.0000  -95.2977 166

 74 omega   59.00   91.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   72.0000  -38.0475 64

 75 omega   58.00   85.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   75.0000   38.3320 54

 76 omega   61.00   86.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   73.0000 -125.5040 50

 77 omega   62.00   89.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   67.0000 -141.4336 54

 78 omega   68.00  102.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   54.0000  102.6459 68

 79 omega   61.00   87.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   76.0000 -141.5889 52

 80 omega   68.00   95.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   51.0000   21.3216 54

 81 omega   60.00   89.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   77.0000  -32.9704 58

 82 omega   77.00  109.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   50.0000   38.8456 64

 83 omega  127.00  154.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   54.0000 -130.7659 54

 84 omega   79.00  110.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   54.0000 -130.7659 62

 85 omega   76.00  103.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   65.0000 -114.6225 54

 86 omega   79.00  108.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   67.0000  -59.7868 58

 87 omega   87.00  114.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000 -180.0000 54

 88 omega   89.00  124.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  150.0000 70

 89 omega   89.00  178.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000    0.0000 178

 90 omega   74.00  139.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -79.0000 -173.0566 130

 91 omega   82.00  109.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -30.0000 54

 92 omega   41.00   67.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -79.0000 -173.0566 52

 93 omega   86.00  157.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000    0.0000 142

 94 omega   89.00  127.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000 -180.0000 76

 95 omega   44.00  114.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000  137.9753 140

 96 omega  121.00  178.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000   90.0000 114

 97 omega   89.00  116.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000   90.0000 54

 98 omega   88.00  122.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  120.0000 68

 99 omega   89.00  178.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000   30.0000 178

100 omega  147.00  176.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000 -120.0000 58

101 omega   88.00  115.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000 -120.0000 54

102 omega  139.00  166.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000 -180.0000 54

103 omega   81.00  106.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000 -180.0000 50

104 omega   79.00  106.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000  -23.4854 54

105 omega   82.00  177.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -60.0000 190

106 omega   82.00  139.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -79.0000  -59.3550 114

107 omega   42.00   74.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -79.0000  -59.3550 64

108 omega  110.00  177.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  150.0000 134

109 omega   80.00  107.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  150.0000 54

110 omega  143.00  170.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  -30.0000 54

111 omega   89.00  118.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  -30.0000 58

112 omega   80.00  106.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  -90.0000 52

113 omega   81.00  106.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000    0.0000 50

114 omega   80.00  107.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000   90.0000 54

115 omega  140.00  167.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  120.0000 54

116 omega   83.00  110.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000  120.0000 54

117 omega   80.00  106.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000   30.0000 52

118 omega   81.00  177.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   77.0000 -150.0000 192

119 omega   88.00  132.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000  -90.0000 88

120 omega   89.00  177.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000   60.0000 176

121 omega   98.00  125.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000 -180.0000 54

122 omega   89.00  177.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   64.0000  -90.0000 176

123 omega   98.00  176.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   50.0000  120.0000 156

124 omega   75.00  100.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000   78.8260 50

125 omega   43.00  114.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -79.0000   34.2013 142

126 omega   88.00  160.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000 -150.0000 144

127 omega   87.00  114.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000  100.3321 54

128 omega   42.00   69.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000  100.3321 54

129 omega   40.00  140.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342  -80.0000 -116.6825 200

130 omega   89.00  138.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000  150.0000 98

131 omega   86.00  113.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2342   38.0000  -90.0000 54

132 omega  -69.00    7.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -90.0000 152

;
_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      -0.0487615000
_diffrn_orient_matrix_UB_12      -0.0117023000
_diffrn_orient_matrix_UB_13      -0.0839098000
_diffrn_orient_matrix_UB_21      0.1479107000
_diffrn_orient_matrix_UB_22      0.0586175000
_diffrn_orient_matrix_UB_23      -0.0119582000
_diffrn_orient_matrix_UB_31      0.1331324000
_diffrn_orient_matrix_UB_32      -0.0695543000
_diffrn_orient_matrix_UB_33      0.0040882000
_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  0.084
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            62862
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.940
_diffrn_reflns_theta_min         3.585
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.566
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77409
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.2457
_exptl_crystal_size_mid          0.0720
_exptl_crystal_size_min          0.0110
_refine_diff_density_max         0.890
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         8565
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0635
_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^)+(0.0958P)^2^+2.1706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6715
_reflns_number_total             8565
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om400711d_si_002.cif
_cod_data_source_block           ga_ak51_5
_cod_original_cell_volume        2324.91(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4081441
_audit_block_refno               1693
_audit_block_usercomment         'AK555, needle, colourless'
_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. Restrained distances
 C20-H20A \\sim C20-H20B \\sim C21-H21A \\sim C21-H21B
 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_shelx_estimated_absorpt_t_max   0.783
_shelx_estimated_absorpt_t_min   0.783
_shelx_res_checksum              32255
_shelxl_version_number           2013-3
_cell_oxdiff_length_a            7.62338(18)
_cell_oxdiff_length_b            16.7982(4)
_cell_oxdiff_length_c            18.4070(5)
_cell_oxdiff_angle_alpha         89.9846(19)
_cell_oxdiff_angle_beta          99.492(2)
_cell_oxdiff_angle_gamma         89.9450(19)
_cell_oxdiff_volume              2324.91(10)
_cell_oxdiff_measurement_reflns_used 12958
_cell_oxdiff_twin_number         2