Tetraaryl pyrenes: photophysical properties, computational studies, crystal structures, and application in OLEDs
Tarek H. El-Assaad; Manuel Auer; Raul Castaneda; Kassem M. Hallal; Fadi M. Jradi; Lorenzo Mosca; Rony S. Khnayzer; Digambara Patra; Tatiana V. Timofeeva; Jean-Luc Bredas; Emil J. W. List-Kratochvil; Brigitte Wex; Bilal R. Kaafarani; Journal of Materials Chemistry C 4 (2016) 3041–3058; doi:10.1039/C5TC02849C

data_7234654
_publ_section_title
;
 Tetraaryl pyrenes: photophysical properties, computational studies,
 crystal structures, and application in OLEDs
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3041
_journal_page_last               3058
_journal_paper_doi               10.1039/C5TC02849C
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C64 H42 O4'
_chemical_formula_sum            'C64 H42 O4'
_chemical_formula_weight         875.04
_chemical_name_systematic        'Pyrene, 1,3,6,8-tetrakis(4-phenoxyphenyl)-'
_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_Int_Tables_number      14
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 106.884(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.87(3)
_cell_length_b                   7.203(12)
_cell_length_c                   19.66(3)
_cell_measurement_reflns_used    620
_cell_measurement_temperature    100
_cell_measurement_theta_max      18.05
_cell_measurement_theta_min      4.22
_cell_volume                     2150(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9797
_diffrn_measured_fraction_theta_max 0.9747
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1045
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8092
_diffrn_reflns_theta_full        19.1772
_diffrn_reflns_theta_max         19.18
_diffrn_reflns_theta_min         4.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7443
_exptl_absorpt_correction_T_min  0.5685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;  
SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) 
was 0.0815 before and 0.0631 after correction. The Ratio of minimum to 
maximum transmission is 0.7638. The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3509
_exptl_crystal_density_meas      .
_exptl_crystal_description       needle
_exptl_crystal_F_000             916.4253
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.4110
_refine_diff_density_min         -0.3211
_refine_diff_density_rms         0.0696
_refine_ls_d_res_high            1.0818
_refine_ls_d_res_low             4.8261
_refine_ls_goodness_of_fit_ref   1.0903
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     304
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0900
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.0081
_refine_ls_shift/su_mean         0.0008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+1.0998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1143
_reflns_number_total             1736
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-3041.cif
_cod_data_source_block           KMH-I-12B
_cod_original_cell_volume        2151(6)
_cod_database_code               7234654
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O2A-C33a
 2 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(O2A)
Uanis(C27) = Uanis(C30)
Uanis(C28) = Uanis(C29)
Uanis(C29) = Uanis(C28)
Uanis(C30) = Uanis(C35a)
Uanis(C31a) = Uanis(C32a)
Uanis(C2) = Uanis(C33a)
4. Others
 Sof(O2A)=Sof(C30a)=Sof(C29a)=Sof(H29a)=Sof(C34a)=Sof(H34a)=Sof(C35a)=
 Sof(H35a)=Sof(C32a)=Sof(H32a)=Sof(C33a)=Sof(H33a)=1-FVAR(1)
 Sof(O2)=Sof(C27)=Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=
 Sof(C31a)=Sof(H31a)=Sof(C2)=Sof(H2)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C46(H46), C40(H40), C45(H45), C52(H52), C51(H51), C49(H49), C48(H48),
 C54(H54), C58(H58), C57(H57), C56(H56), C55(H55), C35(H35), C34(H34), C38(H38),
  C37(H37), C28(H28), C29(H29), C30(H30), C31a(H31a), C2(H2), C29a(H29a),
 C34a(H34a), C35a(H35a), C32a(H32a), C33a(H33a)
5.b Fitted hexagon refined as free rotating group:
 C27(C28,C29,C30,C31a,C2), C30a(C29a,C34a,C35a,C32a,C33a)
;