Functionalization of the "Bay Region" of Perylene in Reaction with 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid: One-Step Approach to 1-Acyl-2-alkylbenzo[ ghi]perylenes.
Głodek, Marta; Makal, Anna; Plażuk, Damian; The Journal of organic chemistry 83 (2018) 14165–14174; doi:10.1021/acs.joc.8b02280

data_4034856
_publ_section_title
;
 Functionalization of the &quot;Bay Region&quot; of Perylene in Reaction
 with 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid:
 One-Step Approach to 1-Acyl-2-alkylbenzo[ ghi]perylenes.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14165
_journal_page_last               14174
_journal_paper_doi               10.1021/acs.joc.8b02280
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C29 H16 O'
_chemical_formula_sum            'C29 H16 O'
_chemical_formula_weight         380.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-10-07
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
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CrysAlisPro, Agilent Technologies,
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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  1 omega  -70.00   31.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega  -70.00   30.00   1.0000   25.0000
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  3 omega -110.00  -84.00   1.0000   25.0000
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  4 omega  -55.00   -9.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega  -50.00   33.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   14.00  102.00   1.0000   25.0000
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  7 omega   12.00  104.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   10.00   87.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   14.00   55.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6563   77.0000  120.0000 41

 10 omega   47.00   80.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6563 -125.0000  -60.0000 33

 11 omega    9.00  110.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6563   77.0000   60.0000 101

 12 omega   23.00   50.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6563   38.0000 -150.0000 27

 13 omega   77.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000   30.0000 101

 14 omega   77.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000   90.0000 101

 15 omega   74.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   24.00  108.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   31.00  115.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega   76.00  160.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   77.00  134.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   77.00  146.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   77.00  153.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000 -150.0000 76

 22 omega   74.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000   30.0000 25

 23 omega   74.00  112.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000 -180.0000 38

 24 omega  117.00  156.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000 -180.0000 39

 25 omega   74.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000 -120.0000 25

 26 omega  104.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000 -120.0000 74

 27 omega   77.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000  150.0000 101

 28 omega   74.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000  -30.0000 25

 29 omega   76.00  101.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   66.0000  -85.2226 25

 30 omega   34.00  131.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551  -61.0000  120.0000 97

 31 omega   76.00  175.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   66.0000  -28.9041 99

 32 omega   74.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000   90.0000 25

 33 omega   77.00  102.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000  -90.0000 25

 34 omega   76.00  160.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   68.0000  -59.6143 84

 35 omega   77.00  103.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000   60.0000 26

 36 omega   76.00  105.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551  -94.0000 -180.0000 29

 37 omega   74.00  100.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000  -60.0000 26

 38 omega   77.00  102.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000  120.0000 25

 39 omega   74.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000 -150.0000 25

 40 omega   75.00  101.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000  120.0000 26

 41 omega   77.00  102.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000 -180.0000 25

 42 omega   37.00  121.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551  -61.0000  -60.0000 84

 43 omega   80.00  107.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551  -94.0000    0.0000 27

 44 omega   74.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   77.0000  150.0000 25

 45 omega  140.00  166.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   76.0000   -7.2835 26

 46 omega   77.00  103.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   61.0000    0.0000 26

 47 omega   74.00  100.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   74.0000 -138.4294 26

 48 omega  150.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   52.0000 -102.8573 28

 49 omega   80.00  106.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      106.1551   52.0000 -102.8573 26
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_diffrn_source                   'sealed X-ray tube'
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear red'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_description       plate
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_exptl_crystal_recrystallization_method 'CHCl3 / MeOH'
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;
 w=1/[\s^2^(Fo^2^)+(0.0715P)^2^+0.8995P]
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_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29)
;
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