Synthesis, regioselective aerobic Pd(ii)-catalyzed C-H bond alkenylation and the photophysical properties of pyrenylphenylpyrazoles.
Flamholc, Rafał; Zakrzewski, Janusz; Makal, Anna; Brosseau, Arnaud; Métivier, Rémi; Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 15 (2016) 580–588; doi:10.1039/c6pp00009f

data_1542913
_publ_section_title
;
 Synthesis, regioselective aerobic Pd(ii)-catalyzed C-H bond alkenylation
 and the photophysical properties of pyrenylphenylpyrazoles.
;
_journal_issue                   4
_journal_name_full
'Photochemical &amp; photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              580
_journal_page_last               588
_journal_paper_doi               10.1039/c6pp00009f
_journal_volume                  15
_journal_year                    2016
_chemical_formula_moiety         'C25 H16 N2'
_chemical_formula_sum            'C25 H16 N2'
_chemical_formula_weight         344.40
_chemical_name_systematic        '1-phenyl-3 (pyren-1-yl)-1H-pyrazole'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
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Olex2 1.2
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2015-03-16 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_measurement_reflns_used    54769
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_cell_measurement_theta_min      2.1380
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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omega____ theta____ kappa____ phi______ frames
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  5 omega  -25.00   79.00   1.0000   35.0000
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  7 omega   18.00  125.00   1.0000   35.0000
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 10 omega   20.00  123.00   1.0000   35.0000
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 11 omega  -29.00   83.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 12 omega   65.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 13 omega    2.00   96.00   1.0000   35.0000
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 14 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   57.0000 -150.0000 103

 15 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   73.00  124.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   73.00  124.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559  125.0000  150.0000 51

 18 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   57.0000    0.0000 103

 19 omega   18.00  124.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 20 omega   16.00  128.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   77.0000  -30.0000 112

 21 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   57.0000   60.0000 103

 22 omega  -80.00   23.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 23 omega  -45.00  -16.00   1.0000   35.0000
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 24 omega  -46.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 25 omega  -45.00  -16.00   1.0000   35.0000
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 26 omega  -46.00  -16.00   1.0000   35.0000
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 27 omega -108.00  -23.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 28 omega  -46.00  -16.00   1.0000   35.0000
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 29 omega  -45.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 30 omega  -45.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
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 31 omega -108.00  -23.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  125.0000  150.0000 85
;
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_diffrn_radiation_wavelength     0.71073
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;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
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Numerical absorption correction based on gaussian integration over
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Empirical absorption correction using spherical harmonics,
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_exptl_crystal_colour            'clear yellow'
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'Re-crystallisation from solvent: dichloromethane/hexane'
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_refine_ls_structure_factor_coef Fsqd
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;
 w=1/[\s^2^(Fo^2^)+(0.0482P)^2^+1.0913P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6pp00009f2.cif
_cod_data_source_block           RFpirazA_exp_198
_cod_depositor_comments
'Adding full bibliography for 1542913--1542914.cif.'
_cod_database_code               1542913
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C25 H16 N2'
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'