#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:03:16 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238273 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/50/1555019.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1555019
loop_
_publ_author_name
'Hahn, Lena'
'Wadepohl, Hubert'
'Gade, Lutz H.'
_publ_section_title
;
 Tetralithiated tetraazaperopyrene as a key intermediate for the synthesis
 of functionalized derivatives.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2266
_journal_page_last               2269
_journal_paper_doi               10.1021/acs.orglett.5b00942
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C32 H4 F26 N4'
_chemical_formula_sum            'C32 H4 F26 N4'
_chemical_formula_weight         938.39
_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_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_block_code                ga_lh10
_audit_creation_date
;
'Fri Sep 26 15:17:22 2014'
;
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
'26.09.2014 15:19:50 CEST UTC+02:00  by encif'
_cell_angle_alpha                103.878(3)
_cell_angle_beta                 100.265(2)
_cell_angle_gamma                98.230(3)
_cell_formula_units_Z            1
_cell_length_a                   6.15317(18)
_cell_length_b                   9.3804(3)
_cell_length_c                   13.8177(4)
_cell_measurement_reflns_used    7785
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      70.4210
_cell_measurement_theta_min      4.9430
_cell_volume                     747.31(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
'encif (Wadepohl, 2009-14); encifer 1.4 (CCDC, 2011)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus, 2007-2009)'
_diffrn_ambient_environment      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 0.983
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -72.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega    2.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0000   78.0000  -82.6278 26

#__ type_ start__ end____ width___ exp.time_
  6 omega    9.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       30.0000   79.0000 -149.6426 28

#__ type_ start__ end____ width___ exp.time_
  7 omega    2.00   27.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       34.0000   80.0000   65.8336 25

#__ type_ start__ end____ width___ exp.time_
  8 omega    7.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   78.0000   92.6666 25

#__ type_ start__ end____ width___ exp.time_
  9 omega    7.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   79.0000 -136.4025 25

#__ type_ start__ end____ width___ exp.time_
 10 omega    6.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   80.0000  129.8525 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   21.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   75.0000  125.6454 51

#__ type_ start__ end____ width___ exp.time_
 12 omega   15.00   40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   78.0000  -72.1337 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   19.00   44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       50.0000   78.0000  -34.8195 25

#__ type_ start__ end____ width___ exp.time_
 14 omega  -17.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -79.0000   97.3656 100

#__ type_ start__ end____ width___ exp.time_
 15 omega   25.00   51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega  -16.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000 -150.0000 99

#__ type_ start__ end____ width___ exp.time_
 17 omega   24.00   51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega   27.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   28.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 20 omega   24.00   50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   23.00   48.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   79.4631 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   29.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega  -13.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -120.0000 87

#__ type_ start__ end____ width___ exp.time_
 24 phi    242.00  327.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
  54.0000   54.0000  -40.0000     -     85

#__ type_ start__ end____ width___ exp.time_
 25 omega   27.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   29.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   67.5280 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   33.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  133.3857 52

#__ type_ start__ end____ width___ exp.time_
 28 omega   93.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -83.5751 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   29.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -14.1496 28

#__ type_ start__ end____ width___ exp.time_
 30 omega   42.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   73.4532 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   30.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -83.5751 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   50.0000   44.4372 26

#__ type_ start__ end____ width___ exp.time_
 33 omega  107.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   50.0000   44.4372 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   36.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -70.1817 26

#__ type_ start__ end____ width___ exp.time_
 35 omega   37.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   29.0000 -146.9669 25

#__ type_ start__ end____ width___ exp.time_
 36 omega   38.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   75.0000  175.6913 45

#__ type_ start__ end____ width___ exp.time_
 37 omega   75.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   69.0000  -10.6321 30

#__ type_ start__ end____ width___ exp.time_
 38 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   69.0000  -10.6321 26

#__ type_ start__ end____ width___ exp.time_
 39 omega   43.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   75.0000  -63.3302 49

#__ type_ start__ end____ width___ exp.time_
 40 omega   90.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   62.0000 -130.7695 26

#__ type_ start__ end____ width___ exp.time_
 41 omega   48.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   62.0000 -130.7695 38

#__ type_ start__ end____ width___ exp.time_
 42 omega   52.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   62.0000   99.9541 33

#__ type_ start__ end____ width___ exp.time_
 43 omega   51.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       74.0000   47.0000   90.2834 35

#__ type_ start__ end____ width___ exp.time_
 44 omega   60.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       78.0000   53.0000   40.9300 26

#__ type_ start__ end____ width___ exp.time_
 45 omega   60.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   66.0000 -110.1582 35

#__ type_ start__ end____ width___ exp.time_
 46 omega   24.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000  -80.0000    0.0537 84

#__ type_ start__ end____ width___ exp.time_
 47 omega   59.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       86.0000   71.0000   47.3096 26

#__ type_ start__ end____ width___ exp.time_
 48 omega   63.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       90.0000   73.0000  -50.0199 64

#__ type_ start__ end____ width___ exp.time_
 49 omega   67.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       94.0000   73.0000   87.0706 39

#__ type_ start__ end____ width___ exp.time_
 50 omega   77.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   61.0000 -174.0762 26

#__ type_ start__ end____ width___ exp.time_
 51 omega  112.00  163.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   73.0000  -92.2682 51

#__ type_ start__ end____ width___ exp.time_
 52 omega   71.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   73.0000  -92.2682 36

#__ type_ start__ end____ width___ exp.time_
 53 omega   75.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   68.0000  124.2388 31

#__ type_ start__ end____ width___ exp.time_
 54 omega  149.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 55 omega  118.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 56 omega   80.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 57 omega   78.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 58 omega   42.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   78.00  163.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
 60 omega   80.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 61 omega   78.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 99

#__ type_ start__ end____ width___ exp.time_
 62 omega   86.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
 63 omega   85.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
 64 omega   48.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -78.0000  141.8375 26

#__ type_ start__ end____ width___ exp.time_
 65 omega   83.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 66 omega   85.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
 67 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 68 omega  148.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 69 omega   86.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
 70 omega   85.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 71 omega   87.00  166.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
 72 omega   77.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000   36.5623 59

#__ type_ start__ end____ width___ exp.time_
 73 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 74 omega   40.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  175.5739 83

#__ type_ start__ end____ width___ exp.time_
 75 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 76 omega   78.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 77 omega   41.00   67.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000   36.5623 26

#__ type_ start__ end____ width___ exp.time_
 78 omega   79.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
 79 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 80 omega   86.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
 81 omega  138.00  166.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 82 omega   83.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 76

#__ type_ start__ end____ width___ exp.time_
 83 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 84 omega   77.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 85 omega  142.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 86 omega   72.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 87 omega   38.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 88 omega   38.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  -61.7736 101

;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω and π scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_orient_matrix_UB_11      0.0217401000
_diffrn_orient_matrix_UB_12      -0.0096320000
_diffrn_orient_matrix_UB_13      0.1109536000
_diffrn_orient_matrix_UB_21      0.2084570000
_diffrn_orient_matrix_UB_22      -0.0719432000
_diffrn_orient_matrix_UB_23      -0.0075541000
_diffrn_orient_matrix_UB_31      0.1528461000
_diffrn_orient_matrix_UB_32      0.1564504000
_diffrn_orient_matrix_UB_33      0.0387325000
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12788
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.741
_diffrn_reflns_theta_min         3.378
_diffrn_source                   'microfocus X-Ray tube'
_diffrn_source_type              'Agilent SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.211
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34k (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,16:31:05)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.085
_exptl_crystal_description       needle
_exptl_crystal_F_000             458
_exptl_crystal_size_max          0.3660
_exptl_crystal_size_mid          0.1406
_exptl_crystal_size_min          0.0581
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2809
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0290
_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/[σ²(Fo²)+(0.0454P)²+0.3208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2581
_reflns_number_total             2809
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b00942_si_002.cif
_cod_data_source_block           ga_lh10
_cod_original_cell_volume        747.30(4)
_cod_database_code               1555019
_audit_block_refno               2190
_audit_block_usercomment         'LH535, needle ,yellow'
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C32 H4 F26 N4'
_chemical_oxdiff_usercomment     'LH535, needle ,yellow'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.809
_shelx_estimated_absorpt_t_min   0.809
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_olex2_submission_special_instructions 'No special instructions were received'
_cell_oxdiff_length_a            6.15317(18)
_cell_oxdiff_length_b            9.3804(3)
_cell_oxdiff_length_c            13.8177(4)
_cell_oxdiff_angle_alpha         103.878(2)
_cell_oxdiff_angle_beta          100.265(2)
_cell_oxdiff_angle_gamma         98.231(2)
_cell_oxdiff_volume              747.30(4)
_cell_oxdiff_measurement_reflns_used 7785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
F1 F 0.20826(15) 0.42227(10) 0.85617(7) 0.0268(2) Uani 1 1 d .
F2 F 0.00561(14) 0.25769(11) 0.71874(7) 0.0260(2) Uani 1 1 d .
F3 F 0.11427(15) 0.14314(11) 0.87493(7) 0.0284(2) Uani 1 1 d .
F4 F 0.26197(15) 0.05543(10) 0.74618(7) 0.0275(2) Uani 1 1 d .
F5 F 0.66634(15) 0.22562(12) 0.84675(8) 0.0330(2) Uani 1 1 d .
F6 F 0.52225(18) 0.08446(13) 0.92972(9) 0.0429(3) Uani 1 1 d .
F7 F 0.53174(17) 0.32176(13) 0.97533(7) 0.0400(3) Uani 1 1 d .
F8 F 0.90805(17) 0.63545(11) 0.93428(7) 0.0320(2) Uani 1 1 d .
F9 F 1.08369(17) 0.82708(12) 0.90150(7) 0.0362(3) Uani 1 1 d .
F10 F 0.72198(17) 0.78582(11) 0.87485(7) 0.0333(2) Uani 1 1 d .
F11 F 0.28128(15) -0.01690(10) 0.45554(8) 0.0317(2) Uani 1 1 d .
F12 F 0.26226(16) 0.04003(11) 0.31271(7) 0.0347(2) Uani 1 1 d .
F13 F 0.07095(14) 0.13394(10) 0.41862(7) 0.0264(2) Uani 1 1 d .
N1 N 0.5410(2) 0.47133(14) 0.76538(9) 0.0198(3) Uani 1 1 d .
N2 N 0.3405(2) 0.26947(14) 0.61992(9) 0.0194(3) Uani 1 1 d .
C1 C 0.6942(2) 0.50731(16) 0.71254(11) 0.0182(3) Uani 1 1 d .
C2 C 0.8829(2) 0.62801(16) 0.76055(10) 0.0197(3) Uani 1 1 d .
C3 C 0.9564(2) 0.33963(17) 0.29069(11) 0.0196(3) Uani 1 1 d .
H3 H 0.836(3) 0.260(2) 0.2558(14) 0.023 Uiso 1 1 d R
C4 C 0.9718(2) 0.41960(16) 0.39537(11) 0.0177(3) Uani 1 1 d .
C5 C 0.8400(2) 0.46404(15) 0.55457(10) 0.0166(3) Uani 1 1 d .
C6 C 0.6762(2) 0.42652(16) 0.60995(10) 0.0175(3) Uani 1 1 d .
C7 C 0.4904(2) 0.30774(16) 0.56591(11) 0.0175(3) Uani 1 1 d .
C8 C 0.4639(2) 0.22517(16) 0.46075(11) 0.0181(3) Uani 1 1 d .
C9 C 0.6161(2) 0.26298(16) 0.40647(11) 0.0186(3) Uani 1 1 d .
H9 H 0.593(3) 0.206(2) 0.3372(14) 0.022 Uiso 1 1 d R
C10 C 0.8086(2) 0.38218(16) 0.45066(10) 0.0172(3) Uani 1 1 d .
C21 C 0.3792(2) 0.35431(16) 0.71572(11) 0.0192(3) Uani 1 1 d .
C23 C 0.2159(2) 0.30603(17) 0.77863(11) 0.0206(3) Uani 1 1 d .
C24 C 0.2721(2) 0.17681(17) 0.82396(11) 0.0210(3) Uani 1 1 d .
C25 C 0.5041(3) 0.20450(19) 0.89672(12) 0.0259(3) Uani 1 1 d .
C26 C 0.8996(3) 0.71923(18) 0.86897(11) 0.0248(3) Uani 1 1 d .
C27 C 0.2682(2) 0.09432(17) 0.41176(11) 0.0199(3) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2 4 0 0.0538 2.0015 3.9980 0.0048 0.0055 0.1296 0.9316
-3 3 -5 0.1178 -3.0005 3.0013 -4.9982 -0.6487 -0.8036 -0.1826
-2 -3 -1 0.0477 -2.0015 -2.9981 -1.0039 -0.1260 -0.1940 -0.8139
1 4 -8 0.0084 0.9979 3.9998 -7.9972 -0.9041 -0.0193 0.4685
-1 -3 8 0.0299 -0.9974 -3.0001 7.9983 0.8947 -0.0525 -0.3120
-4 1 2 0.1414 -3.9979 1.0011 2.0010 0.1255 -0.9205 -0.3769
4 -3 -3 0.1533 3.9965 -3.0004 -3.0035 -0.2175 1.0716 0.0251
-2 -4 1 0.0455 -2.0011 -3.9982 0.9954 0.1055 -0.1370 -0.8928
2 -4 5 0.1340 2.0002 -4.0006 4.9969 0.6364 0.6670 -0.1266
-1 -5 -1 0.1042 -1.0026 -4.9980 -1.0061 -0.0853 0.1582 -0.9742
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C21 N1 C1 115.40(12) .
C21 N2 C7 114.98(13) .
N1 C1 C2 120.10(13) .
N1 C1 C6 121.29(14) .
C6 C1 C2 118.60(12) .
C1 C2 C26 119.16(12) .
C3 C2 C1 120.41(13) 2_766
C3 C2 C26 120.43(14) 2_766
C2 C3 H3 117.0(11) 2_766
C2 C3 C4 121.97(14) 2_766
C4 C3 H3 120.9(11) .
C5 C4 C3 118.63(13) 2_766
C5 C4 C10 119.14(13) 2_766
C10 C4 C3 122.19(14) .
C4 C5 C6 119.18(13) 2_766
C4 C5 C10 122.30(13) 2_766
C10 C5 C6 118.52(13) .
C1 C6 C5 121.12(13) .
C7 C6 C1 116.93(12) .
C7 C6 C5 121.94(13) .
N2 C7 C6 121.60(13) .
N2 C7 C8 119.97(13) .
C6 C7 C8 118.43(12) .
C7 C8 C27 119.69(12) .
C9 C8 C7 119.99(13) .
C9 C8 C27 120.31(13) .
C8 C9 H9 117.6(11) .
C8 C9 C10 122.32(13) .
C10 C9 H9 120.1(11) .
C4 C10 C5 118.56(14) .
C4 C10 C9 122.67(13) .
C5 C10 C9 118.76(13) .
N1 C21 N2 129.73(13) .
N1 C21 C23 115.29(12) .
N2 C21 C23 114.95(13) .
F1 C23 F2 107.49(11) .
F1 C23 C21 110.67(12) .
F1 C23 C24 107.98(11) .
F2 C23 C21 109.56(11) .
F2 C23 C24 106.52(12) .
C21 C23 C24 114.33(11) .
F3 C24 F4 108.17(12) .
F3 C24 C23 108.34(11) .
F3 C24 C25 107.82(11) .
F4 C24 C23 108.51(11) .
F4 C24 C25 106.87(12) .
C25 C24 C23 116.85(13) .
F5 C25 C24 109.90(12) .
F6 C25 F5 108.02(13) .
F6 C25 C24 108.83(13) .
F7 C25 F5 108.92(13) .
F7 C25 F6 109.37(13) .
F7 C25 C24 111.73(13) .
F8 C26 F9 107.41(13) .
F8 C26 F10 107.87(12) .
F8 C26 C2 112.07(13) .
F9 C26 F10 107.19(13) .
F9 C26 C2 111.36(12) .
F10 C26 C2 110.72(12) .
F11 C27 F12 107.87(12) .
F11 C27 F13 106.89(11) .
F11 C27 C8 112.00(12) .
F12 C27 C8 110.77(12) .
F13 C27 F12 107.15(12) .
F13 C27 C8 111.92(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C23 1.3459(17) .
F2 C23 1.3547(17) .
F3 C24 1.3422(16) .
F4 C24 1.3506(17) .
F5 C25 1.3292(17) .
F6 C25 1.3238(19) .
F7 C25 1.3139(19) .
F8 C26 1.3304(18) .
F9 C26 1.3345(19) .
F10 C26 1.3395(19) .
F11 C27 1.3306(17) .
F12 C27 1.3329(17) .
F13 C27 1.3315(16) .
N1 C1 1.3450(18) .
N1 C21 1.323(2) .
N2 C7 1.3476(18) .
N2 C21 1.3306(19) .
C1 C2 1.435(2) .
C1 C6 1.414(2) .
C2 C3 1.356(2) 2_766
C2 C26 1.5138(19) .
C3 C2 1.356(2) 2_766
C3 H3 0.940(19) .
C3 C4 1.4401(19) .
C4 C5 1.415(2) 2_766
C4 C10 1.4199(19) .
C5 C4 1.415(2) 2_766
C5 C6 1.4240(19) .
C5 C10 1.4206(19) .
C6 C7 1.407(2) .
C7 C8 1.4414(19) .
C8 C9 1.3594(19) .
C8 C27 1.517(2) .
C9 H9 0.953(19) .
C9 C10 1.436(2) .
C21 C23 1.5296(18) .
C23 C24 1.545(2) .
C24 C25 1.541(2) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
F1 C23 C24 F3 57.79(15) . .
F1 C23 C24 F4 175.02(10) . .
F1 C23 C24 C25 -64.15(15) . .
F2 C23 C24 F3 -57.41(14) . .
F2 C23 C24 F4 59.81(13) . .
F2 C23 C24 C25 -179.36(11) . .
F3 C24 C25 F5 174.67(12) . .
F3 C24 C25 F6 56.56(16) . .
F3 C24 C25 F7 -64.31(16) . .
F4 C24 C25 F5 58.58(16) . .
F4 C24 C25 F6 -59.52(15) . .
F4 C24 C25 F7 179.60(11) . .
N1 C1 C2 C3 176.89(13) . 2_766
N1 C1 C2 C26 -3.4(2) . .
N1 C1 C6 C5 -179.39(12) . .
N1 C1 C6 C7 0.3(2) . .
N1 C21 C23 F1 25.45(17) . .
N1 C21 C23 F2 143.81(12) . .
N1 C21 C23 C24 -96.73(15) . .
N2 C7 C8 C9 -179.49(13) . .
N2 C7 C8 C27 -0.64(19) . .
N2 C21 C23 F1 -156.33(12) . .
N2 C21 C23 F2 -37.96(16) . .
N2 C21 C23 C24 81.49(16) . .
C1 N1 C21 N2 -2.6(2) . .
C1 N1 C21 C23 175.35(12) . .
C1 C2 C26 F8 60.06(18) . .
C1 C2 C26 F9 -179.59(13) . .
C1 C2 C26 F10 -60.43(18) . .
C1 C6 C7 N2 -2.1(2) . .
C1 C6 C7 C8 178.60(12) . .
C2 C1 C6 C5 -0.5(2) . .
C2 C1 C6 C7 179.22(12) . .
C2 C3 C4 C5 0.5(2) 2_766 2_766
C2 C3 C4 C10 -177.40(13) 2_766 .
C3 C2 C26 F8 -120.22(15) 2_766 .
C3 C2 C26 F9 0.1(2) 2_766 .
C3 C2 C26 F10 119.29(15) 2_766 .
C3 C4 C10 C5 178.21(12) . .
C3 C4 C10 C9 -0.4(2) . .
C4 C5 C6 C1 2.5(2) 2_766 .
C4 C5 C6 C7 -177.20(12) 2_766 .
C4 C5 C10 C4 -0.4(2) 2_766 .
C4 C5 C10 C9 178.28(12) 2_766 .
C5 C4 C10 C5 0.4(2) 2_766 .
C5 C4 C10 C9 -178.24(12) 2_766 .
C5 C6 C7 N2 177.59(12) . .
C5 C6 C7 C8 -1.7(2) . .
C6 C1 C2 C3 -2.0(2) . 2_766
C6 C1 C2 C26 177.68(13) . .
C6 C5 C10 C4 179.96(12) . .
C6 C5 C10 C9 -1.38(19) . .
C6 C7 C8 C9 -0.2(2) . .
C6 C7 C8 C27 178.66(12) . .
C7 N2 C21 N1 0.9(2) . .
C7 N2 C21 C23 -177.06(12) . .
C7 C8 C9 C10 1.3(2) . .
C7 C8 C27 F11 -64.37(16) . .
C7 C8 C27 F12 175.16(12) . .
C7 C8 C27 F13 55.65(17) . .
C8 C9 C10 C4 178.15(13) . .
C8 C9 C10 C5 -0.5(2) . .
C9 C8 C27 F11 114.47(15) . .
C9 C8 C27 F12 -6.00(19) . .
C9 C8 C27 F13 -125.51(14) . .
C10 C5 C6 C1 -177.83(12) . .
C10 C5 C6 C7 2.5(2) . .
C21 N1 C1 C2 -177.11(12) . .
C21 N1 C1 C6 1.8(2) . .
C21 N2 C7 C6 1.60(19) . .
C21 N2 C7 C8 -179.12(12) . .
C21 C23 C24 F3 -178.57(12) . .
C21 C23 C24 F4 -61.34(16) . .
C21 C23 C24 C25 59.49(17) . .
C23 C24 C25 F5 -63.11(17) . .
C23 C24 C25 F6 178.78(12) . .
C23 C24 C25 F7 57.91(17) . .
C27 C8 C9 C10 -177.58(12) . .
