1,3,6,8-Tetraazapyrenes: Synthesis, Solid-State Structures, and Properties as Redox-Active Materials
Sonja Geib; Susanne C. Martens; Ute Zschieschang; Florian Lombeck; Hubert Wadepohl; Hagen Klauk; Lutz H. Gade; Journal of Organic Chemistry 77 (2012) 6107–6116; doi:10.1021/jo300894p

data_4027310
_publ_section_title
;
 1,3,6,8-Tetraazapyrenes: Synthesis, Solid-State Structures, and
 Properties as Redox-Active Materials
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6107
_journal_page_last               6116
_journal_paper_doi               10.1021/jo300894p
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C28 H10 F10 N4 O'
_chemical_formula_weight         608.40
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   fmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_sh16
_audit_creation_date
;
'Thu Oct 27 16:07:30 2011'
;
_audit_creation_method
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_audit_update_record             'Fri Oct 28 11:39:08 CEST 2011'
_cell_angle_alpha                90.00
_cell_angle_beta                 92.620(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.2334(7)
_cell_length_b                   12.6047(3)
_cell_length_c                   8.5605(2)
_cell_measurement_reflns_used    15549
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      72.4739
_cell_measurement_theta_min      4.0764
_cell_volume                     2288.74(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_temperature      99.9(3)
_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 0.989
_diffrn_measurement_details
;
  1 omega   -9.00   21.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -90.0000 30

  2 omega  -37.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -90.0000 27

  3 omega   17.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.0000   77.0000   26.0000 27

  4 omega  -16.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       10.0000   77.0000   26.0000 26

  5 omega    3.00   28.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000   79.0000  -95.0000 25

  6 omega   11.00   36.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   79.0000   37.0000 25

  7 omega  -39.00  -13.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   30.0000 26

  8 omega -105.00  -57.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  120.0000 48

  9 omega  -46.00  -15.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -120.0000 31

 10 omega  -46.00   30.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000   90.0000 76

 11 omega  -72.00    5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   77.0000 -180.0000 77

 12 omega  -13.00   27.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   77.0000   90.0000 40

 13 omega  -53.00  -12.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000 -180.0000 41

 14 omega  -42.00  -13.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -30.0000 29

 15 omega  -47.00  -16.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  120.0000 31

 16 omega  -42.00   24.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  -60.0000 66

 17 omega   14.00   39.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000   72.0000 25

 18 omega   15.00   40.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000   22.0000 25

 19 omega   19.00   44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  170.0000 25

 20 omega   19.00   44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000   88.0000 25

 21 omega   28.00   54.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000 -173.0000 26

 22 omega   19.00   44.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  -49.0000 25

 23 omega   71.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   77.0000 -173.0000 27

 24 omega   72.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   -5.0000 51

 25 omega   23.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -135.0000 25

 26 omega   23.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   36.0000 25

 27 omega   24.00   50.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   -5.0000 26

 28 omega   23.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   26.0000 25

 29 omega   23.00   48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  134.0000 25

 30 omega   28.00   76.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1328  -77.0000  -90.0000 48

 31 omega   29.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  -49.0000 98

 32 omega   29.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  -98.0000 79

 33 omega   93.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  110.0000 34

 34 omega   31.00   56.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  110.0000 25

 35 omega   30.00   58.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   72.0000 28

 36 omega   33.00  131.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  142.0000 98

 37 omega   34.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   73.0000   63.0000 43

 38 omega   19.00  103.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000  -79.0000  -18.0000 84

 39 omega   51.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000  -80.0000  169.0000 58

 40 omega   69.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   19.0000  -87.0000 25

 41 omega  112.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000  -60.0000 65

 42 omega   80.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000  -60.0000 25

 43 omega   74.00  100.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -79.0000  -31.0000 26

 44 omega   89.00  117.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000 -120.0000 28

 45 omega   41.00   71.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -79.0000  -31.0000 30

 46 omega   69.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -79.0000  149.0000 26

 47 omega   71.00  112.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -80.0000  -66.0000 41

 48 omega  127.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000 -150.0000 49

 49 omega   80.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000 -150.0000 26

 50 omega   40.00   65.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -80.0000  -66.0000 25

 51 omega  128.00  159.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000  -30.0000 31

 52 omega   80.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000  -30.0000 26

 53 omega   89.00  148.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000  -60.0000 59

 54 omega  113.00  139.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -80.0000   32.0000 26

 55 omega  111.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000 -120.0000 66

 56 omega   82.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000 -120.0000 26

 57 omega   81.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000 -180.0000 25

 58 omega  112.00  177.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000 -180.0000 65

 59 omega   40.00   98.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -80.0000   32.0000 58

 60 omega  101.00  136.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   45.0000  -60.0000 35

 61 omega   88.00  113.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   45.0000  -90.0000 25

 62 omega   89.00  115.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000  -90.0000 26

 63 omega   87.00  112.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   45.0000 -120.0000 25

 64 omega  144.00  170.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000   60.0000 26

 65 omega   91.00  146.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000   90.0000 55

 66 omega  125.00  151.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000  120.0000 26

 67 omega   91.00  117.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000  -90.0000 26

 68 omega   91.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000   90.0000 85

 69 omega   80.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000  120.0000 26

 70 omega   41.00  141.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -80.0000 -151.0000 100

 71 omega  124.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000   30.0000 52

 72 omega   63.00  138.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -80.0000   87.0000 75

 73 omega   80.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000  -90.0000 26

 74 omega   88.00  151.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   45.0000   90.0000 63

 75 omega   83.00  112.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000 -150.0000 29

 76 omega   89.00  115.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000 -150.0000 26

 77 omega   90.00  122.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000   30.0000 32

 78 omega   80.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000    0.0000 26

 79 omega   88.00  113.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000    0.0000 25

 80 omega   87.00  113.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000   30.0000 26

 81 omega   89.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000    0.0000 89

 82 omega   90.00  115.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000  -30.0000 25

 83 omega   80.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000   90.0000 26

 84 omega   80.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   77.0000  150.0000 26

 85 omega   89.00  115.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000  120.0000 26

 86 omega   88.00  113.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   45.0000 -150.0000 25

 87 omega   90.00  119.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000   60.0000 29

 88 omega   88.00  113.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   45.0000   60.0000 25

 89 omega   86.00  156.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000 -180.0000 70

 90 omega   87.00  112.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000  150.0000 25

 91 omega   89.00  118.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000 -180.0000 29

 92 omega  121.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000  150.0000 55

 93 omega  142.00  174.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000  -90.0000 32

 94 omega   89.00  115.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   61.0000  150.0000 26

 95 omega  -73.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -19.0000  104.0000 117

 96 omega  -13.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       18.0000   78.0000   -2.0000 62

 97 omega    3.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000   79.0000  -95.0000 44

 98 omega  -48.00   30.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000   60.0000 78

 99 omega  -63.00   26.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000  -90.0000 89

100 omega -111.00  -21.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  150.0000 90

101 omega  -48.00   30.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -180.0000 78

102 omega   18.00   46.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000  -19.0000 28

103 omega   19.00   49.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000   88.0000 30

104 omega   19.00   47.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   79.0000  -49.0000 28

105 omega   19.00   49.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  170.0000 30

106 omega   25.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000  -80.0000 99

107 omega   23.00   49.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -135.0000 26

108 omega   23.00   49.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  134.0000 26

109 omega   23.00   49.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   26.0000 26

110 omega   24.00  124.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   -5.0000 100

111 omega  -18.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1328    0.0000  120.0000 146

112 omega  -18.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1328    0.0000  240.0000 146

113 omega  -18.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1328    0.0000  120.0000 146

114 omega  -18.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1328    0.0000    0.0000 146

115 omega  -18.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       55.1328    0.0000    0.0000 146

116 omega   29.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  -98.0000 99

117 omega   28.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   72.0000 100

118 omega   30.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000   88.0000 98

119 omega   34.00  131.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   73.0000   63.0000 97

120 omega   33.00  132.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   75.0000  142.0000 99

121 omega    3.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000  -79.0000  -18.0000 102

122 omega    7.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000  -80.0000  169.0000 103

123 omega   39.00  142.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -80.0000   32.0000 103

124 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -30.0000 -120.0000 53

125 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -30.0000  -60.0000 53

126 omega   81.00  128.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000   60.0000 47

127 omega   87.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   45.0000  -90.0000 91

128 omega   81.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657   30.0000  120.0000 97

129 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -30.0000  -30.0000 53

130 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -30.0000  150.0000 53

131 omega   38.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -30.0000   30.0000 53

132 omega   40.00  140.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.2657  -77.0000 -120.0000 100

;
_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      -0.0183581000
_diffrn_orient_matrix_UB_12      0.1157670000
_diffrn_orient_matrix_UB_13      0.0325933000
_diffrn_orient_matrix_UB_21      0.0023468000
_diffrn_orient_matrix_UB_22      -0.0235409000
_diffrn_orient_matrix_UB_23      0.1768379000
_diffrn_orient_matrix_UB_31      0.0702721000
_diffrn_orient_matrix_UB_32      0.0310371000
_diffrn_orient_matrix_UB_33      0.0113845000
_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  0.0534
_diffrn_reflns_av_sigmaI/netI    0.1061
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            35335
_diffrn_reflns_theta_full        66.97
_diffrn_reflns_theta_max         72.4739
_diffrn_reflns_theta_min         4.0764
_diffrn_source                   'Agilent SuperNova (Cu) x-ray Source'
_exptl_absorpt_coefficient_mu    1.485
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1216
_exptl_crystal_recrystallization_method thf
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
;
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+1.6717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                2084
_reflns_number_total             2260
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300894p_si_002_07.cif
_cod_data_source_block           ga_sh16-sr
_cod_original_cell_volume        2288.76(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4027310
_audit_block_refno               1350
_cell_oxdiff_length_a            21.2234(8)
_cell_oxdiff_length_b            12.6125(6)
_cell_oxdiff_length_c            8.5598(4)
_cell_oxdiff_angle_alpha         89.905(4)
_cell_oxdiff_angle_beta          92.700(4)
_cell_oxdiff_angle_gamma         90.008(4)
_cell_oxdiff_volume              2288.76(18)
_cell_oxdiff_measurement_reflns_used 15549
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1