data_1 _audit_creation_method SHELXL-97 _publ_contact_author_name 'Dr. Hicham Fenniri' _publ_contact_author_address ; Department of Chemistry University of Alberta Edmonton, Alberta T6G 2G2 Canada ; _publ_contact_author_email hicham.fenniri@nrc-cnrc.gc.ca _publ_contact_author_fax '1(780)6411750' _publ_contact_author_phone '1(780)6411601' _publ_contact_letter ; To: Cambridge Crystallographic Data Centre Please accept the following CIF data for a structure to be published in Energy & Fuels. Please forward any questions concerning this CIF to Bob McDonald (Bob.McDonald@ualberta.ca). ; _publ_requested_journal 'Energy & Fuels' _publ_section_title ; Pyrene derivatives of 2,2'-bipyridine as models for asphaltenes: synthesis, characterization, and supramolecular organization ; loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Tan, Xiaoli' . ; Department of Chemical and Materials Engineering University of Alberta Edmonton, Alberta T6G 2G6 Canada ; 'Fenniri, Hicham' . ; National Institute of Nanotechnology and Department of Chemistry University of Alberta Edmonton, Alberta T6G 2M9 Canada ; 'Gray, Murray R.' . ; Department of Chemical and Materials Engineering University of Alberta Edmonton, Alberta T6G 2G6 Canada ; _chemical_name_systematic ; 4,4'-bis(2-(4-pyrenyl)ethyl)-2,2'-bipyridine ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C46 H32 N2' _chemical_formula_sum 'C46 H32 N2' _chemical_formula_weight 612.74 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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' _cell_length_a 4.6343(11) _cell_length_b 14.097(3) _cell_length_c 23.290(5) _cell_angle_alpha 90.00 _cell_angle_beta 95.506(4) _cell_angle_gamma 90.00 _cell_volume 1514.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2972 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.74 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9741 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10235 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2685 _reflns_number_gt 1511 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0941P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2685 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1269 _refine_ls_R_factor_gt 0.0660 _refine_ls_wR_factor_ref 0.1834 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group 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_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N 0.0571(18) 0.0272(14) 0.0423(16) 0.0031(12) 0.0021(13) -0.0005(12) C1 0.0406(17) 0.0280(17) 0.0351(18) 0.0032(13) 0.0046(14) -0.0011(13) C2 0.0436(18) 0.0296(17) 0.0391(18) 0.0006(14) 0.0060(15) 0.0014(14) C3 0.0378(18) 0.0433(19) 0.0336(18) 0.0013(15) 0.0034(14) -0.0090(15) C4 0.057(2) 0.0302(17) 0.0417(19) -0.0052(15) 0.0045(16) -0.0108(16) C5 0.062(2) 0.0285(18) 0.047(2) -0.0028(15) 0.0026(17) -0.0024(16) C6 0.0437(19) 0.048(2) 0.0391(18) -0.0010(15) 0.0032(15) -0.0062(15) C7 0.0430(18) 0.0381(18) 0.0433(19) -0.0005(14) 0.0036(15) -0.0086(15) C11 0.0398(18) 0.0310(18) 0.0396(19) 0.0030(14) 0.0075(14) -0.0051(14) C12 0.051(2) 0.0306(18) 0.0452(19) -0.0048(15) 0.0057(16) -0.0074(15) C13 0.049(2) 0.0207(16) 0.052(2) 0.0005(14) 0.0125(16) 0.0017(14) C14 0.0439(18) 0.0256(16) 0.0377(18) 0.0059(14) 0.0087(14) 0.0004(14) C15 0.051(2) 0.0337(18) 0.047(2) 0.0122(16) 0.0092(17) 0.0067(16) C16 0.051(2) 0.048(2) 0.043(2) 0.0128(17) 0.0025(16) -0.0010(17) C17 0.0437(19) 0.0403(19) 0.0360(18) 0.0057(15) 0.0068(15) -0.0058(15) C18 0.055(2) 0.057(2) 0.042(2) 0.0008(17) 0.0011(17) -0.0145(18) C19 0.071(2) 0.044(2) 0.048(2) -0.0110(17) 0.0076(19) -0.0164(19) C20 0.062(2) 0.0317(18) 0.052(2) -0.0075(16) 0.0095(18) -0.0097(16) C21 0.0412(18) 0.0281(17) 0.0442(19) -0.0013(14) 0.0117(15) -0.0028(14) C22 0.052(2) 0.0225(16) 0.051(2) 0.0025(15) 0.0113(16) 0.0040(15) C23 0.0430(18) 0.0299(17) 0.0405(18) 0.0085(14) 0.0026(15) 0.0036(14) C24 0.0341(16) 0.0236(15) 0.0346(17) 0.0027(12) 0.0061(13) -0.0025(13) C25 0.0370(16) 0.0251(16) 0.0357(17) 0.0007(13) 0.0108(14) -0.0030(13) C26 0.0384(17) 0.0289(17) 0.0301(16) 0.0030(13) 0.0083(14) -0.0033(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag 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_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 _geom_angle_publ_flag 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_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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag 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 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.260 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.060