(Oligo-)Thiophene Functionalized Tetraazaperopyrenes: Donor-Acceptor Dyes and Ambipolar Organic Semiconductors.
Hahn, Lena; Hermannsdorfer, André; Günther, Benjamin; Wesp, Tobias; Bühler, Bastian; Zschieschang, Ute; Wadepohl, Hubert; Klauk, Hagen; Gade, Lutz H.; The Journal of organic chemistry 82 (2017) 12492–12502; doi:10.1021/acs.joc.7b02286

data_4033165
_publ_section_title
;
 (Oligo-)Thiophene Functionalized Tetraazaperopyrenes: Donor-Acceptor Dyes
 and Ambipolar Organic Semiconductors.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12492
_journal_page_last               12502
_journal_paper_doi               10.1021/acs.joc.7b02286
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C68 H64 F14 N4 S4'
_chemical_formula_weight         1331.47
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_ah1
_audit_creation_date
;
'Tue Oct 13 11:14:17 2015'
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Olex2 1.2
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;
_audit_update_record
'13.10.2015 11:17:13 CEST UTC+02:00  encif 1.35'
_cell_angle_alpha                107.5526(18)
_cell_angle_beta                 100.5745(16)
_cell_angle_gamma                111.0829(18)
_cell_formula_units_Z            3
_cell_length_a                   15.3304(3)
_cell_length_b                   17.3728(4)
_cell_length_c                   21.0398(4)
_cell_measurement_reflns_used    27623
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.3510
_cell_measurement_theta_min      4.4490
_cell_volume                     4708.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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'encif (Wadepohl, 2009-14); encifer 1.5 (CCDC, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9621
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
  1 omega  -21.00   55.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 76

  2 omega  -22.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -60.0000 91

  3 omega  -50.00  -19.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  150.0000 31

  4 omega  -28.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -30.0000 52

  5 omega  -19.00   42.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 61

  6 omega  -54.00  -29.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -30.0000 25

  7 omega  -40.00    2.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.0000  118.0000  144.2251 42

  8 omega  -26.00    9.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0000  111.0000  171.9231 35

  9 omega  -10.00   15.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000  103.0000  -15.4145 25

 10 omega    0.00   25.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   94.0000 -147.9720 25

 11 omega    5.00   30.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   90.0000  167.2694 25

 12 omega    6.00   31.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       42.0000   88.0000  116.8377 25

 13 omega   13.00   38.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   83.0000  -73.3873 25

 14 omega   12.00   37.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000  109.3278 25

 15 omega   12.00   37.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000   -3.5907 25

 16 omega   15.00   40.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   79.0000   31.9777 25

 17 omega   14.00   39.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   80.0000  -98.0474 25

 18 omega   12.00   37.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000  -41.7301 25

 19 omega   14.00   39.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   81.0000 -129.3967 25

 20 omega   13.00   38.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   83.0000   63.0820 25

 21 omega   12.00   37.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000 -177.0276 25

 22 omega   18.00   43.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000   39.3892 25

 23 omega   18.00   43.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000  -33.8269 25

 24 omega   18.00   43.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000  161.7605 25

 25 omega   19.00   44.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  122.5724 25

 26 omega   18.00   43.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   80.0000  -56.4243 25

 27 omega   26.00   51.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   76.0000  163.3748 25

 28 omega   24.00   51.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -171.6238 27

 29 omega   23.00  104.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  120.0000 81

 30 omega  -15.00   74.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 89

 31 omega   25.00   50.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000    0.0000 25

 32 omega  -16.00   82.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  150.0000 98

 33 omega   24.00   51.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -90.0000 27

 34 omega  -14.00   75.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -150.0000 89

 35 omega   23.00   48.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000  145.2783 25

 36 omega   25.00   52.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 27

 37 omega   23.00   48.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000 -136.3174 25

 38 omega   29.00   56.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 27

 39 omega   24.00   51.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   90.0000 27

 40 omega   23.00   48.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   96.5443 25

 41 omega   30.00   57.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  -65.3401 27

 42 omega   30.00   57.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  -50.7083 27

 43 omega   29.00   54.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   25.3440 25

 44 omega   33.00   60.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000 -136.4612 27

 45 omega   29.00   56.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000 -171.2117 27

 46 omega   30.00   57.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000   56.1331 27

 47 omega   30.00   55.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000    2.9090 25

 48 omega   29.00   77.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  152.6692 48

 49 omega   30.00   55.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000  106.5880 25

 50 omega   29.00   56.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   75.0000   39.1992 27

 51 omega   31.00   56.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  -96.8569 25

 52 omega   31.00   56.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  168.5809 25

 53 omega   31.00   58.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   60.3303 27

 54 omega   28.00   55.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -34.3697 27

 55 omega   31.00   61.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   74.0000  -79.2029 30

 56 omega   30.00   79.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -18.6930 49

 57 omega   34.00   59.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -167.2380 25

 58 omega  105.00  132.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -167.2380 27

 59 omega   34.00   61.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000   86.0046 27

 60 omega   37.00   64.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   74.0000  -12.9891 27

 61 omega   39.00   66.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   73.0000    1.3599 27

 62 omega   32.00   67.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   77.0000  103.5125 35

 63 omega   34.00   59.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -177.7179 25

 64 omega   36.00   64.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000   38.7279 28

 65 omega   35.00  124.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       62.0000   76.0000 -122.9728 89

 66 omega   37.00   62.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000 -160.0365 25

 67 omega   38.00   63.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   76.0000  -53.4415 25

 68 omega   38.00   64.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   74.0000   11.0768 26

 69 omega   43.00  105.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   72.0000 -150.0082 62

 70 omega   53.00   82.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   59.0000  -54.5353 29

 71 omega   43.00   71.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   74.0000   72.1838 28

 72 omega   47.00  132.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   64.0000  -92.2181 85

 73 omega   67.00  114.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   68.0000    4.8625 47

 74 omega   48.00   75.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   70.0000  -45.5248 27

 75 omega   48.00   74.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   70.0000  166.5734 26

 76 omega   52.00   82.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   62.0000 -101.9607 30

 77 omega   51.00   84.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   72.0000   -5.0936 33

 78 omega   58.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   58.0000   44.2272 31

 79 omega   50.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   74.0000  140.1085 31

 80 omega   52.00   79.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   70.0000  -89.4438 27

 81 omega   48.00   95.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   77.0000  110.2165 47

 82 omega   48.00   78.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   77.0000   92.0693 30

 83 omega   72.00   99.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   48.0000 -153.5996 27

 84 omega   55.00   90.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   72.0000 -152.7659 35

 85 omega   60.00   93.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   61.0000   84.9329 33

 86 omega   58.00   95.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   67.0000 -135.5913 37

 87 omega   62.00   88.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   54.0000  -72.4965 26

 88 omega   53.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   75.0000  157.9167 56

 89 omega   56.00   86.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   77.0000   17.1056 30

 90 omega   63.00   90.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   64.0000  -33.8681 27

 91 omega   66.00  134.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   58.0000 -136.8401 68

 92 omega   60.00   92.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   71.0000  113.1466 32

 93 omega   63.00   94.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   47.0000  -44.1464 31

 94 omega   71.00  111.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   51.0000   78.3241 40

 95 omega   64.00   91.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   70.0000  129.1253 27

 96 omega   61.00  112.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   75.0000   87.7324 51

 97 omega   69.00   96.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   67.0000  138.1014 27

 98 omega   65.00  140.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   70.0000 -126.2527 75

 99 omega   68.00   95.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   70.0000  -48.8158 27

100 omega   72.00  126.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   66.0000  -10.0646 54

101 omega   77.00  113.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   54.0000  108.7719 36

102 omega   74.00  127.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   67.0000 -170.9884 53

103 omega   73.00   99.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      102.0000   75.0000   45.9520 26

104 omega  121.00  163.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 42

105 omega   85.00  119.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  120.0000 34

106 omega   80.00  111.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 31

107 omega   78.00  104.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 26

108 omega   86.00  150.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -30.0000 64

109 omega   85.00  112.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000    0.0000 27

110 omega   79.00  106.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 27

111 omega   42.00  131.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -64.0000  150.0000 89

112 omega   85.00  174.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   30.0000 89

113 omega   78.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 99

114 omega   79.00  104.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 25

115 omega   78.00  105.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 27

116 omega  129.00  156.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 27

117 omega   79.00  106.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 27

118 omega  129.00  178.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 49

119 omega   78.00  128.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 50

120 omega  133.00  165.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 32

121 omega   78.00  105.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 27

122 omega   78.00  105.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 27

123 omega   80.00  171.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 91

124 omega   79.00  104.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 25

125 omega   85.00  171.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 86

126 omega   75.00  116.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 41

127 omega   37.00   62.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 25

128 omega   78.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 99

129 omega   84.00  155.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 71

130 omega  107.00  146.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -92.0000    0.0000 39

131 omega   36.00   97.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -92.0000    0.0000 61

132 omega   85.00  174.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -90.0000 89

133 omega  102.00  129.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -92.0000  -60.0000 27

134 omega   47.00  100.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -92.0000  -60.0000 53

135 omega   37.00  113.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 76

136 omega   85.00  174.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   66.0000  153.7385 89

137 omega   79.00  105.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   75.0000 -131.3930 26

138 omega   80.00  155.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   73.0000  138.4425 75

139 omega   83.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 26

140 omega   82.00  153.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -150.0000 71

141 omega   38.00  101.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 63

142 omega   86.00  111.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   90.0000 25

143 omega   85.00  171.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -60.0000 86

144 omega  -26.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -120.0000 98

145 omega  -72.00   26.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 98

146 omega  -30.00   70.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  120.0000 100

147 omega  -26.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000 -180.0000 98

148 omega  -21.00   69.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 90

149 omega  -26.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000  -30.0000 98

150 omega  -23.00    9.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0000  112.0000 -175.1799 32

151 omega  -29.00    1.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0000  121.0000  -40.5912 30

;
_diffrn_measurement_device       'four-circle 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      0.0162320000
_diffrn_orient_matrix_UB_12      0.0690906000
_diffrn_orient_matrix_UB_13      -0.0338013000
_diffrn_orient_matrix_UB_21      -0.1127706000
_diffrn_orient_matrix_UB_22      -0.0337996000
_diffrn_orient_matrix_UB_23      -0.0292085000
_diffrn_orient_matrix_UB_31      0.0043780000
_diffrn_orient_matrix_UB_32      0.0696046000
_diffrn_orient_matrix_UB_33      0.0679282000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            126219
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.994
_diffrn_reflns_theta_min         3.978
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.147
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       plate
_exptl_crystal_F_000             2070
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1240
_refine_ls_number_reflns         17947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0760P)^2^+3.7716P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13532
_reflns_number_total             17947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02286_si_002.cif
_cod_data_source_block           ga_ah1
_cod_depositor_comments
'Adding full bibliography for 4033164--4033168.cif.'
_cod_original_cell_volume        4708.83(17)
_cod_database_code               4033165
_audit_block_refno               2551
_audit_block_usercomment         'AH-012, plate, black'
_chemical_oxdiff_formula         'C68 H64 F14 N4 S4'
_chemical_oxdiff_usercomment     'AH-012, plate, black'
_shelx_estimated_absorpt_t_max   0.814
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_shelxl_version_number           2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,
 H37B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B),
 C47(H47A,H47B), C53(H53A,H53B), C54(H54A,H54B), C55(H55A,H55B), C56(H56A,H56B),
  C57(H57A,H57B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B), C66(H66A,
 H66B), C67(H67A,H67B), C133(H13A,H13B), C134(H13C,H13D), C135(H13E,H13F),
 C136(H13G,H13H), C137(H13I,H13J), C143(H14A,H14B), C144(H14C,H14D), C145(H14E,
 H14F), C146(H14G,H14H), C147(H14I,H14J)
2.b Aromatic/amide H refined with riding coordinates:
 C31(H31), C32(H32), C41(H41), C42(H42), C51(H51), C52(H52), C61(H61),
 C62(H62), C131(H131), C132(H132), C141(H141), C142(H142)
2.c Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C48(H48A,H48B,H48C), C58(H58A,H58B,H58C), C68(H68A,H68B,
 H68C), C138(H13K,H13L,H13M), C148(H14K,H14L,H14M)
;
_shelx_res_checksum              44540
_olex2_submission_special_instructions 'No special instructions were received'
_cell_oxdiff_length_a            15.3304(3)
_cell_oxdiff_length_b            17.3728(4)
_cell_oxdiff_length_c            21.0398(4)
_cell_oxdiff_angle_alpha         107.5526(18)
_cell_oxdiff_angle_beta          100.5745(16)
_cell_oxdiff_angle_gamma         111.0829(18)
_cell_oxdiff_volume              4708.84(16)
_cell_oxdiff_measurement_reflns_used 27623