#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/46/7234654.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7234654
loop_
_publ_author_name
'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'
_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       'φ and ω 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 λ/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/[σ²(Fo²)+(0.0495P)²+1.0998P] where P=(Fo²+2Fc²)/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)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
_atom_site_disorder_group
O1 O 0.1112(3) 0.1562(6) 0.4332(2) 0.0632(12) Uani 1.000000 . .
C46 C 0.3763(3) 0.8314(8) 0.4099(3) 0.0456(16) Uani 1.000000 . .
H46 H 0.3336(3) 0.7449(8) 0.3843(3) 0.0548(19) Uiso 1.000000 R .
C42 C 0.4200(4) 0.7972(8) 0.4831(3) 0.0411(15) Uani 1.000000 . .
C43 C 0.4900(4) 0.9201(7) 0.5179(3) 0.0427(15) Uani 1.000000 . .
C44 C 0.5409(4) 0.8849(8) 0.5889(3) 0.0433(15) Uani 1.000000 . .
C39 C 0.5249(4) 0.7230(9) 0.6228(3) 0.0454(15) Uani 1.000000 . .
C40 C 0.4547(4) 0.6107(8) 0.5886(4) 0.0490(16) Uani 1.000000 . .
H40 H 0.4432(4) 0.5043(8) 0.6130(4) 0.0588(19) Uiso 1.000000 R .
C41 C 0.4005(4) 0.6446(8) 0.5210(3) 0.0436(15) Uani 1.000000 . .
C45 C 0.6061(4) 1.0155(9) 0.6245(3) 0.0474(16) Uani 1.000000 . .
H45 H 0.6378(4) 0.9958(9) 0.6729(3) 0.0569(19) Uiso 1.000000 R .
C47 C 0.3260(4) 0.5171(9) 0.4918(3) 0.0461(16) Uani 1.000000 . .
C52 C 0.2416(5) 0.5790(8) 0.4561(3) 0.0491(16) Uani 1.000000 . .
H52 H 0.2319(5) 0.7079(8) 0.4469(3) 0.0589(19) Uiso 1.000000 R .
C51 C 0.1711(4) 0.4566(10) 0.4336(3) 0.0514(17) Uani 1.000000 . .
H51 H 0.1143(4) 0.5003(10) 0.4081(3) 0.062(2) Uiso 1.000000 R .
C50 C 0.1855(5) 0.2713(10) 0.4492(3) 0.0511(16) Uani 1.000000 . .
C49 C 0.2672(5) 0.2051(8) 0.4834(3) 0.0479(16) Uani 1.000000 . .
H49 H 0.2761(5) 0.0760(8) 0.4924(3) 0.0575(19) Uiso 1.000000 R .
C48 C 0.3365(4) 0.3266(9) 0.5046(3) 0.0502(16) Uani 1.000000 . .
H48 H 0.3932(4) 0.2797(9) 0.5288(3) 0.0602(19) Uiso 1.000000 R .
C53 C 0.1004(4) 0.0256(9) 0.3792(3) 0.0505(16) Uani 1.000000 . .
C54 C 0.1519(4) 0.0210(9) 0.3335(3) 0.0560(17) Uani 1.000000 . .
H54 H 0.1985(4) 0.1073(9) 0.3381(3) 0.067(2) Uiso 1.000000 R .
C58 C 0.1337(4) -0.1134(10) 0.2805(3) 0.0545(17) Uani 1.000000 . .
H58 H 0.1704(4) -0.1242(10) 0.2502(3) 0.065(2) Uiso 1.000000 R .
C57 C 0.0636(5) -0.2298(10) 0.2718(3) 0.0671(19) Uani 1.000000 . .
H57 H 0.0499(5) -0.3173(10) 0.2340(3) 0.080(2) Uiso 1.000000 R .
C56 C 0.0122(4) -0.2210(10) 0.3177(4) 0.0642(19) Uani 1.000000 . .
H56 H -0.0362(4) -0.3034(10) 0.3116(4) 0.077(2) Uiso 1.000000 R .
C55 C 0.0305(4) -0.0955(9) 0.3713(3) 0.0488(16) Uani 1.000000 . .
H55 H -0.0043(4) -0.0908(9) 0.4033(3) 0.0586(19) Uiso 1.000000 R .
C36 C 0.5830(4) 0.6628(8) 0.6928(3) 0.0498(16) Uani 1.000000 . .
C35 C 0.5530(4) 0.6472(8) 0.7522(4) 0.0598(18) Uani 1.000000 . .
H35 H 0.4947(4) 0.6851(8) 0.7493(4) 0.072(2) Uiso 1.000000 R .
C34 C 0.6061(7) 0.5781(10) 0.8148(4) 0.079(2) Uani 1.000000 . .
H34 H 0.5854(7) 0.5695(10) 0.8554(4) 0.095(3) Uiso 1.000000 R .
C38 C 0.7238(5) 0.5390(11) 0.7611(5) 0.096(3) Uani 1.000000 . .
H38 H 0.7826(5) 0.5035(11) 0.7650(5) 0.115(3) Uiso 1.000000 R .
C37 C 0.6698(5) 0.6085(8) 0.6997(3) 0.0643(18) Uani 1.000000 . .
H37 H 0.6918(5) 0.6208(8) 0.6598(3) 0.077(2) Uiso 1.000000 R .
C33 C 0.6889(8) 0.5221(10) 0.8180(4) 0.098(3) Uani 1.000000 . .
O2 O 0.7172(9) 0.4281(17) 0.8903(6) 0.080(3) Uani 0.490(5) . 1
C27 C 0.7889(8) 0.2865(11) 0.8775(7) 0.050(3) Uani 0.490(5) . 1
C28 C 0.7269(6) 0.1541(14) 0.8440(6) 0.065413 Uani 0.490(5) G 1
H28 H 0.6690(6) 0.1913(14) 0.8184(6) 0.078496 Uiso 0.490(5) R 1
C29 C 0.7498(6) -0.0327(13) 0.8482(5) 0.0654134707219 Uani 0.490(5) G 1
H29 H 0.7075(6) -0.1232(13) 0.8254(5) 0.078496 Uiso 0.490(5) R 1
C30 C 0.8345(7) -0.0872(12) 0.8858(6) 0.050(3) Uani 0.490(5) G 1
H30 H 0.8502(7) -0.2149(12) 0.8886(6) 0.061(3) Uiso 0.490(5) R 1
C31a C 0.8965(6) 0.0453(16) 0.9192(7) 0.089(5) Uani 0.490(5) G 1
H31a H 0.9544(6) 0.0081(16) 0.9449(7) 0.106(6) Uiso 0.490(5) R 1
C2 C 0.8736(7) 0.2321(14) 0.9150(7) 0.063(4) Uani 0.490(5) G 1
H2 H 0.9159(7) 0.3226(14) 0.9379(7) 0.076(5) Uiso 0.490(5) R 1
O2A O 0.7636(7) 0.4870(15) 0.8763(5) 0.080(3) Uani 0.510(5) D 2
C30a C 0.7784(6) 0.3072(17) 0.8956(6) 0.077(6) Uani 0.510(5) . 2
C29a C 0.7509(5) 0.1317(19) 0.8687(5) 0.080(5) Uani 0.510(5) G 2
H29a H 0.6910(5) 0.1110(19) 0.8430(5) 0.096(6) Uiso 0.510(5) R 2
C34a C 0.8110(8) -0.0134(14) 0.8794(5) 0.073(5) Uani 0.510(5) G 2
H34a H 0.7923(8) -0.1333(14) 0.8611(5) 0.088(6) Uiso 0.510(5) R 2
C35a C 0.8987(7) 0.0169(12) 0.9170(6) 0.050(3) Uani 0.510(5) G 2
H35a H 0.9398(7) -0.0823(12) 0.9243(6) 0.061(3) Uiso 0.510(5) R 2
C32a C 0.9262(5) 0.1923(13) 0.9438(6) 0.089(5) Uani 0.510(5) G 2
H32a H 0.9861(5) 0.2130(13) 0.9695(6) 0.106(6) Uiso 0.510(5) R 2
C33a C 0.8661(7) 0.3375(12) 0.9331(6) 0.063(4) Uani 0.510(5) DG 2
H33a H 0.8849(7) 0.4573(12) 0.9515(6) 0.076(5) Uiso 0.510(5) R 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C53 O1 C50 118.8(4) . .
C45 C46 C42 122.0(5) 3_676 .
C43 C42 C46 117.2(5) . .
C41 C42 C46 123.4(6) . .
C41 C42 C43 119.3(5) . .
C43 C43 C42 121.1(7) 3_676 .
C44 C43 C42 120.1(5) . .
C39 C44 C43 119.1(5) . .
C45 C44 C43 119.4(6) . .
C45 C44 C39 121.5(6) . .
C40 C39 C44 119.1(5) . .
C36 C39 C44 122.3(6) . .
C36 C39 C40 118.5(6) . .
C41 C40 C39 123.7(5) . .
C40 C41 C42 118.4(6) . .
C47 C41 C42 123.6(6) . .
C47 C41 C40 118.1(6) . .
C44 C45 C46 121.0(5) . 3_676
C52 C47 C41 122.8(6) . .
C48 C47 C41 120.1(6) . .
C48 C47 C52 116.9(6) . .
C51 C52 C47 121.6(5) . .
C50 C51 C52 118.6(6) . .
C51 C50 O1 116.8(6) . .
C49 C50 O1 121.5(6) . .
C49 C50 C51 121.5(6) . .
C48 C49 C50 119.5(6) . .
C49 C48 C47 121.9(6) . .
C54 C53 O1 123.2(6) . .
C55 C53 O1 115.4(6) . .
C55 C53 C54 121.3(6) . .
C58 C54 C53 118.1(6) . .
C57 C58 C54 120.5(5) . .
C56 C57 C58 120.2(6) . .
C55 C56 C57 120.3(6) . .
C56 C55 C53 119.4(5) . .
C35 C36 C39 122.1(6) . .
C37 C36 C39 120.0(6) . .
C37 C36 C35 117.7(6) . .
C34 C35 C36 120.9(6) . .
C33 C34 C35 119.0(7) . .
C33 C38 C37 116.9(7) . .
C38 C37 C36 122.5(6) . .
C38 C33 C34 122.8(6) . .
C28 C27 O2 94.3 . .
C2 C27 O2 135.9 . .
C2 C27 C28 120.0 . .
C29 C28 C27 120.0 . .
C30 C29 C28 120.0 . .
C31a C30 C29 120.0 . .
C2 C31a C30 120.0 . .
C31a C2 C27 120.0 . .
C29a C30a O2A 139.0 . .
C33a C30a O2A 93.7 . .
C33a C30a C29a 120.0 . .
C34a C29a C30a 120.0 . .
C35a C34a C29a 120.0 . .
C32a C35a C34a 120.0 . .
C33a C32a C35a 120.0 . .
C32a C33a C30a 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C50 1.400(7) .
O1 C53 1.391(6) .
C46 C42 1.427(7) .
C46 C45 1.364(7) 3_676
C42 C43 1.430(7) .
C42 C41 1.411(7) .
C43 C43 1.431(10) 3_676
C43 C44 1.418(7) .
C44 C39 1.403(7) .
C44 C45 1.423(7) .
C39 C40 1.382(7) .
C39 C36 1.483(8) .
C40 C41 1.379(7) .
C41 C47 1.475(7) .
C47 C52 1.393(7) .
C47 C48 1.397(7) .
C52 C51 1.392(7) .
C51 C50 1.373(8) .
C50 C49 1.362(7) .
C49 C48 1.372(7) .
C53 C54 1.380(7) .
C53 C55 1.384(7) .
C54 C58 1.390(7) .
C58 C57 1.365(8) .
C57 C56 1.383(8) .
C56 C55 1.355(7) .
C36 C35 1.388(8) .
C36 C37 1.400(8) .
C35 C34 1.368(9) .
C34 C33 1.359(10) .
C38 C37 1.357(8) .
C38 C33 1.390(11) .
C33 O2 1.520(13) .
C33 O2A 1.412(12) .
O2 C27 1.601(16) .
C27 C28 1.3900 .
C27 C2 1.3900 .
C28 C29 1.3900 .
C29 C30 1.3900 .
C30 C31a 1.3900 .
C31a C2 1.3900 .
O2A C30a 1.351(14) .
C30a C29a 1.3900 .
C30a C33a 1.3900 .
C29a C34a 1.3900 .
C34a C35a 1.3900 .
C35a C32a 1.3900 .
C32a C33a 1.3900 .
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O2A C33a 1 2.0000 0.0010 0.0004
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 23109686
