Tetralithiated tetraazaperopyrene as a key intermediate for the synthesis of functionalized derivatives.
Hahn, Lena; Wadepohl, Hubert; Gade, Lutz H.; Organic letters 17 (2015) 2266–2269; doi:10.1021/acs.orglett.5b00942

data_1555019
_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
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;
'Fri Sep 26 15:17:22 2014'
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Olex2 1.2
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;
_audit_update_record             '26.09.2014 15:19:50 CEST UTC+02:00  by encif'
_cell_angle_alpha                103.878(3)
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_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)
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_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)'
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'encif (Wadepohl, 2009-14); encifer 1.4 (CCDC, 2011)'
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_diffrn_ambient_environment      N~2~
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_diffrn_measurement_details
;
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omega____ theta____ kappa____ phi______ frames
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  2 omega    2.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega  -17.00   15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega  -72.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega    2.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega    9.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega    2.00   27.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega    7.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega    7.00   32.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega    6.00   31.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   21.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   15.00   40.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   78.0000  -72.1337 25

 13 omega   19.00   44.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega  -17.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 15 omega   25.00   51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega  -16.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   24.00   51.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega   27.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   28.00   58.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 30

 20 omega   24.00   50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -180.0000 26

 21 omega   23.00   48.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   78.0000   79.4631 25

 22 omega   29.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 26

 23 omega  -13.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -120.0000 87

 24 phi    242.00  327.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
  54.0000   54.0000  -40.0000     -     85

 25 omega   27.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -120.0000 26

 26 omega   29.00   55.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000   67.5280 26

 27 omega   33.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  133.3857 52

 28 omega   93.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -83.5751 26

 29 omega   29.00   57.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   77.0000  -14.1496 28

 30 omega   42.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000   73.4532 26

 31 omega   30.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       58.0000   76.0000  -83.5751 26

 32 omega   44.00   70.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   50.0000   44.4372 26

 33 omega  107.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   50.0000   44.4372 26

 34 omega   36.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   77.0000  -70.1817 26

 35 omega   37.00   62.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       66.0000   29.0000 -146.9669 25

 36 omega   38.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 37 omega   75.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 38 omega   43.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 39 omega   43.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 40 omega   90.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 41 omega   48.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 42 omega   52.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 43 omega   51.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 44 omega   60.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
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 45 omega   60.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       82.0000   66.0000 -110.1582 35

 46 omega   24.00  108.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 47 omega   59.00   85.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 48 omega   63.00  127.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 49 omega   67.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 50 omega   77.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       98.0000   61.0000 -174.0762 26

 51 omega  112.00  163.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 52 omega   71.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 53 omega   75.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 54 omega  149.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 55 omega  118.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 27

 56 omega   80.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26

 57 omega   78.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 27

 58 omega   42.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 26

 59 omega   78.00  163.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 85

 60 omega   80.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 26

 61 omega   78.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 62 omega   86.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 63 omega   85.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  -30.0000 90

 64 omega   48.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -78.0000  141.8375 26

 65 omega   83.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 94

 66 omega   85.00  174.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000  150.0000 89

 67 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 68 omega  148.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 69 omega   86.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000   30.0000 30

 70 omega   85.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000    0.0000 26

 71 omega   87.00  166.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -180.0000 79

 72 omega   77.00  136.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000   36.5623 59

 73 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 74 omega   40.00  123.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000  175.5739 83

 75 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 26

 76 omega   78.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 27

 77 omega   41.00   67.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -80.0000   36.5623 26

 78 omega   79.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 98

 79 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 26

 80 omega   86.00  171.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   64.0000 -150.0000 85

 81 omega  138.00  166.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 28

 82 omega   83.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 76

 83 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

 84 omega   77.00  135.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 58

 85 omega  142.00  168.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

 86 omega   72.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 26

 87 omega   38.00   64.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 26

 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       '\w and \p scans'
_diffrn_measurement_specimen_support 'polyimid foil'
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_diffrn_orient_matrix_UB_21      0.2084570000
_diffrn_orient_matrix_UB_22      -0.0719432000
_diffrn_orient_matrix_UB_23      -0.0075541000
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_diffrn_orient_matrix_UB_32      0.1564504000
_diffrn_orient_matrix_UB_33      0.0387325000
_diffrn_radiation_monochromator  mirror
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_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
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_diffrn_source                   'microfocus X-Ray tube'
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;
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
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_exptl_crystal_F_000             458
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_exptl_crystal_size_mid          0.1406
_exptl_crystal_size_min          0.0581
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_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refxyz
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_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0314
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_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0454P)^2^+0.3208P] where P=(Fo^2^+2Fc^2^)/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
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_reflns_threshold_expression     'I > 2\s(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_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
;
_shelx_res_checksum              23543
_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