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_1542914
_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-5 (pyren-1-yl)-1H-pyrazole'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-02-21
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Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
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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_formula_units_Z            4
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_cell_measurement_reflns_used    11712
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_computing_cell_refinement
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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)
(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)
(compiled Jan 14 2014,18:38:05)
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  1 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  2 omega -110.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega -110.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega   27.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  5 omega   36.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  6 omega   94.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   94.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   83.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega   32.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 10 omega   32.00   91.00   1.0000    1.0000
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 11 omega   13.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1984   77.0000    0.0000 102

 12 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1984  -99.0000  150.0000 81

 13 omega   13.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1984   77.0000  -90.0000 102

 14 omega   79.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130   61.0000    0.0000 95

 15 omega   65.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 16 omega   79.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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 17 omega   79.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130   61.0000  120.0000 64

 18 omega   25.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130  -94.0000 -120.0000 84
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_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_Laue_measured_fraction_full 0.992
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_diffrn_reflns_number            16576
_diffrn_reflns_point_group_measured_fraction_full 0.992
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_diffrn_reflns_theta_max         74.073
_diffrn_reflns_theta_min         4.134
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
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_exptl_crystal_description       prism
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_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/hexane'
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_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.0124(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
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_refine_ls_R_factor_all          0.0427
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_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+0.4294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6pp00009f2.cif
_cod_data_source_block           exp_195_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 1542913--1542914.cif.'
_cod_database_code               1542914
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C25 H16 N2'
_diffrn_oxdiff_twin_integration_method simultaneous
_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'