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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/43/1504339.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_1504339
loop_
_publ_author_name
'Tan, Xiaoli'
'Fenniri, Hicham'
'Gray, Murray R.'
_publ_section_title
;
 Pyrene Derivatives of 2,2′-Bipyridine as Models for Asphaltenes:
 Synthesis, Characterization, and Supramolecular Organization†
;
_journal_issue                   2
_journal_name_full               'Energy & Fuels'
_journal_page_first              715
_journal_paper_doi               10.1021/ef700395g
_journal_volume                  22
_journal_year                    2008
_chemical_formula_moiety         'C46 H32 N2'
_chemical_formula_sum            'C46 H32 N2'
_chemical_formula_weight         612.74
_chemical_name_systematic
;

 4,4'-bis(2-(4-pyrenyl)ethyl)-2,2'-bipyridine

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.506(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.6343(11)
_cell_length_b                   14.097(3)
_cell_length_c                   23.290(5)
_cell_measurement_reflns_used    2972
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.74
_cell_measurement_theta_min      2.27
_cell_volume                     1514.5(6)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0835
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10235
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.69
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0941P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1834
_reflns_number_gt                1511
_reflns_number_total             2685
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ef700395g.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1504339
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N N -0.0685(5) 0.11840(17) 0.02329(10) 0.0424(7) Uani 1 1 d .
C1 C 0.0573(6) 0.0322(2) 0.02357(12) 0.0345(7) Uani 1 1 d .
C2 C 0.2759(6) 0.0057(2) 0.06465(12) 0.0373(8) Uani 1 1 d .
H2 H 0.3601 -0.0555 0.0630 0.045 Uiso 1 1 calc R
C3 C 0.3743(6) 0.0675(2) 0.10834(12) 0.0382(8) Uani 1 1 d .
C4 C 0.2421(7) 0.1563(2) 0.10780(13) 0.0431(8) Uani 1 1 d .
H4 H 0.3002 0.2018 0.1367 0.052 Uiso 1 1 calc R
C5 C 0.0289(7) 0.1772(2) 0.06539(13) 0.0460(8) Uani 1 1 d .
H5 H -0.0568 0.2384 0.0659 0.055 Uiso 1 1 calc R
C6 C 0.6039(6) 0.0396(2) 0.15424(12) 0.0436(8) Uani 1 1 d .
H6A H 0.7199 0.0963 0.1666 0.052 Uiso 1 1 calc R
H6B H 0.7351 -0.0068 0.1382 0.052 Uiso 1 1 calc R
C7 C 0.4803(6) -0.0038(2) 0.20650(12) 0.0415(8) Uani 1 1 d .
H7A H 0.3377 0.0407 0.2207 0.050 Uiso 1 1 calc R
H7B H 0.3769 -0.0631 0.1947 0.050 Uiso 1 1 calc R
C11 C 0.7093(6) -0.0250(2) 0.25431(12) 0.0366(8) Uani 1 1 d .
C12 C 0.8218(7) -0.1166(2) 0.26143(13) 0.0421(8) Uani 1 1 d .
H12 H 0.7441 -0.1655 0.2365 0.050 Uiso 1 1 calc R
C13 C 1.0403(7) -0.1382(2) 0.30318(13) 0.0401(8) Uani 1 1 d .
H13 H 1.1091 -0.2017 0.3065 0.048 Uiso 1 1 calc R
C14 C 1.1635(6) -0.07028(19) 0.34061(12) 0.0354(7) Uani 1 1 d .
C15 C 1.3924(6) -0.0888(2) 0.38400(13) 0.0436(8) Uani 1 1 d .
H15 H 1.4653 -0.1517 0.3883 0.052 Uiso 1 1 calc R
C16 C 1.5100(7) -0.0211(2) 0.41919(14) 0.0477(9) Uani 1 1 d .
H16 H 1.6642 -0.0367 0.4475 0.057 Uiso 1 1 calc R
C17 C 1.4056(6) 0.0747(2) 0.41463(12) 0.0398(8) Uani 1 1 d .
C18 C 1.5235(7) 0.1467(3) 0.45100(13) 0.0517(9) Uani 1 1 d .
H18 H 1.6799 0.1328 0.4792 0.062 Uiso 1 1 calc R
C19 C 1.4153(8) 0.2373(2) 0.44635(14) 0.0541(9) Uani 1 1 d .
H19 H 1.4949 0.2855 0.4717 0.065 Uiso 1 1 calc R
C20 C 1.1929(7) 0.2585(2) 0.40532(13) 0.0481(9) Uani 1 1 d .
H20 H 1.1208 0.3216 0.4027 0.058 Uiso 1 1 calc R
C21 C 1.0703(6) 0.1906(2) 0.36754(13) 0.0374(7) Uani 1 1 d .
C22 C 0.8417(6) 0.2095(2) 0.32496(13) 0.0413(8) Uani 1 1 d .
H22 H 0.7663 0.2722 0.3218 0.050 Uiso 1 1 calc R
C23 C 0.7249(6) 0.1430(2) 0.28851(13) 0.0379(8) Uani 1 1 d .
H23 H 0.5723 0.1598 0.2602 0.045 Uiso 1 1 calc R
C24 C 0.8277(6) 0.04610(18) 0.29170(11) 0.0306(7) Uani 1 1 d .
C25 C 1.0541(6) 0.02447(18) 0.33461(12) 0.0321(7) Uani 1 1 d .
C26 C 1.1779(6) 0.09581(19) 0.37239(11) 0.0321(7) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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_3
C5 N C1 116.3(3) .
N C1 C2 122.4(3) .
N C1 C1 115.1(3) 3
C2 C1 C1 122.5(3) 3
C1 C2 C3 120.7(3) .
C2 C3 C4 116.5(3) .
C2 C3 C6 121.7(3) .
C4 C3 C6 121.8(3) .
C5 C4 C3 119.3(3) .
N C5 C4 124.9(3) .
C3 C6 C7 112.5(2) .
C11 C7 C6 112.4(2) .
C12 C11 C24 117.9(3) .
C12 C11 C7 120.3(3) .
C24 C11 C7 121.8(3) .
C13 C12 C11 122.2(3) .
C12 C13 C14 121.8(3) .
C13 C14 C15 123.9(3) .
C13 C14 C25 117.7(3) .
C15 C14 C25 118.4(3) .
C16 C15 C14 122.5(3) .
C15 C16 C17 120.7(3) .
C18 C17 C26 119.6(3) .
C18 C17 C16 121.9(3) .
C26 C17 C16 118.5(3) .
C19 C18 C17 120.6(3) .
C20 C19 C18 120.2(3) .
C19 C20 C21 121.8(3) .
C20 C21 C22 123.5(3) .
C20 C21 C26 118.6(3) .
C22 C21 C26 117.9(3) .
C23 C22 C21 122.9(3) .
C22 C23 C24 121.1(3) .
C11 C24 C25 120.3(3) .
C11 C24 C23 122.4(3) .
C25 C24 C23 117.3(2) .
C24 C25 C26 121.0(2) .
C24 C25 C14 120.2(3) .
C26 C25 C14 118.8(3) .
C17 C26 C25 121.0(3) .
C17 C26 C21 119.2(3) .
C25 C26 C21 119.8(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N C5 1.329(4) .
N C1 1.348(4) .
C1 C2 1.376(4) .
C1 C1 1.482(5) 3
C2 C3 1.383(4) .
C3 C4 1.393(4) .
C3 C6 1.487(4) .
C4 C5 1.361(4) .
C6 C7 1.522(4) .
C7 C11 1.493(4) .
C11 C12 1.396(4) .
C11 C24 1.405(4) .
C12 C13 1.369(4) .
C13 C14 1.381(4) .
C14 C15 1.417(4) .
C14 C25 1.431(4) .
C15 C16 1.339(4) .
C16 C17 1.435(4) .
C17 C18 1.399(4) .
C17 C26 1.404(4) .
C18 C19 1.373(4) .
C19 C20 1.369(4) .
C20 C21 1.385(4) .
C21 C22 1.406(4) .
C21 C26 1.427(4) .
C22 C23 1.344(4) .
C23 C24 1.446(4) .
C24 C25 1.411(4) .
C25 C26 1.421(4) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C5 N C1 C2 -0.4(4) . . .
C5 N C1 C1 179.5(3) . . 3
N C1 C2 C3 0.7(4) . . .
C1 C1 C2 C3 -179.2(3) 3 . .
C1 C2 C3 C4 -0.4(4) . . .
C1 C2 C3 C6 178.1(2) . . .
C2 C3 C4 C5 -0.1(4) . . .
C6 C3 C4 C5 -178.6(3) . . .
C1 N C5 C4 -0.1(5) . . .
C3 C4 C5 N 0.4(5) . . .
C2 C3 C6 C7 -90.8(3) . . .
C4 C3 C6 C7 87.6(3) . . .
C3 C6 C7 C11 -175.7(2) . . .
C6 C7 C11 C12 -97.9(3) . . .
C6 C7 C11 C24 79.3(3) . . .
C24 C11 C12 C13 0.0(4) . . .
C7 C11 C12 C13 177.2(3) . . .
C11 C12 C13 C14 -0.3(4) . . .
C12 C13 C14 C15 -179.2(3) . . .
C12 C13 C14 C25 0.3(4) . . .
C13 C14 C15 C16 179.1(3) . . .
C25 C14 C15 C16 -0.3(4) . . .
C14 C15 C16 C17 0.5(5) . . .
C15 C16 C17 C18 179.7(3) . . .
C15 C16 C17 C26 -0.1(4) . . .
C26 C17 C18 C19 1.1(5) . . .
C16 C17 C18 C19 -178.7(3) . . .
C17 C18 C19 C20 -1.0(5) . . .
C18 C19 C20 C21 0.0(5) . . .
C19 C20 C21 C22 179.9(3) . . .
C19 C20 C21 C26 0.8(4) . . .
C20 C21 C22 C23 179.9(3) . . .
C26 C21 C22 C23 -1.0(4) . . .
C21 C22 C23 C24 0.8(5) . . .
C12 C11 C24 C25 0.4(4) . . .
C7 C11 C24 C25 -176.8(2) . . .
C12 C11 C24 C23 -179.3(3) . . .
C7 C11 C24 C23 3.6(4) . . .
C22 C23 C24 C11 179.8(3) . . .
C22 C23 C24 C25 0.2(4) . . .
C11 C24 C25 C26 179.4(2) . . .
C23 C24 C25 C26 -1.0(4) . . .
C11 C24 C25 C14 -0.4(4) . . .
C23 C24 C25 C14 179.2(3) . . .
C13 C14 C25 C24 0.1(4) . . .
C15 C14 C25 C24 179.6(2) . . .
C13 C14 C25 C26 -179.7(3) . . .
C15 C14 C25 C26 -0.3(4) . . .
C18 C17 C26 C25 179.7(3) . . .
C16 C17 C26 C25 -0.5(4) . . .
C18 C17 C26 C21 -0.2(4) . . .
C16 C17 C26 C21 179.6(3) . . .
C24 C25 C26 C17 -179.2(2) . . .
C14 C25 C26 C17 0.6(4) . . .
C24 C25 C26 C21 0.8(4) . . .
C14 C25 C26 C21 -179.4(3) . . .
C20 C21 C26 C17 -0.7(4) . . .
C22 C21 C26 C17 -179.8(3) . . .
C20 C21 C26 C25 179.3(3) . . .
C22 C21 C26 C25 0.2(4) . . .
N C1 C1 N 180.0 . 3 3
N C1 C1 C2 0.1(5) . 3 3
C2 C1 C1 C2 180.0 . 3 3
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 86211065
