#------------------------------------------------------------------------------ #$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $ #$Revision: 966 $ #$URL: svn://www.crystallography.net/cod/cif/2/2202504.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_2202504 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2003 _journal_volume 59 _journal_page_first o1748 _journal_page_last o1750 _publ_section_title ; 4,5-Bis(1-naphthoxy)phthalonitrile ; loop_ _publ_author_name 'Karakurt, Tuncay' 'Din\,cer, Muharrem' 'Nesuhi, Akdemir' 'Kantar, Cihan' 'A\(gar, Erbil' _chemical_formula_moiety 'C28 H16 N2 O2' _chemical_formula_sum 'C28 H16 N2 O2' _chemical_formula_iupac 'C28 H16 N2 O2' _chemical_formula_weight 412.43 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9667(14) _cell_length_b 10.4946(15) _cell_length_c 11.2637(16) _cell_angle_alpha 116.931(11) _cell_angle_beta 99.441(11) _cell_angle_gamma 93.570(12) _cell_volume 1023.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _exptl_crystal_density_diffrn 1.338 _diffrn_ambient_temperature 293(2) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 0.49340(14) 0.74607(14) 0.05429(13) 0.0515(4) Uani d . 1 . . O O2 0.68250(14) 0.73471(14) 0.24528(14) 0.0570(4) Uani d . 1 . . O N1 0.0331(2) 0.4099(2) 0.0951(2) 0.0783(7) Uani d . 1 . . N N2 0.3128(2) 0.4235(2) 0.4124(2) 0.0856(7) Uani d . 1 . . N C1 0.4542(2) 0.6767(2) 0.1247(2) 0.0462(5) Uani d . 1 . . C C2 0.3205(2) 0.6088(2) 0.0916(2) 0.0484(6) Uani d . 1 . . C C3 0.2824(2) 0.53677(19) 0.1609(2) 0.0476(6) Uani d . 1 . . C C4 0.3782(2) 0.53688(19) 0.2657(2) 0.0469(5) Uani d . 1 . . C C5 0.5139(2) 0.6031(2) 0.2981(2) 0.0495(6) Uani d . 1 . . C C6 0.1432(3) 0.4648(2) 0.1256(2) 0.0594(6) Uani d . 1 . . C C7 0.3379(2) 0.4710(2) 0.3449(2) 0.0575(6) Uani d . 1 . . C C8 0.5520(2) 0.67022(19) 0.2256(2) 0.0461(5) Uani d . 1 . . C C9 0.5321(2) 0.8979(2) 0.1315(2) 0.0472(6) Uani d . 1 . . C C10 0.4707(3) 0.9800(3) 0.2325(3) 0.0597(7) Uani d . 1 . . C C11 0.5131(3) 1.1311(3) 0.3027(3) 0.0717(8) Uani d . 1 . . C C12 0.6118(3) 1.1931(3) 0.2671(3) 0.0669(8) Uani d . 1 . . C C13 0.6744(2) 1.1090(2) 0.1608(2) 0.0510(6) Uani d . 1 . . C C14 0.6360(2) 0.9574(2) 0.0909(2) 0.0445(5) Uani d . 1 . . C C15 0.6994(2) 0.8740(3) -0.0135(2) 0.0555(6) Uani d . 1 . . C C16 0.7986(3) 0.9372(3) -0.0503(3) 0.0692(7) Uani d . 1 . . C C17 0.8361(3) 1.0876(3) 0.0190(3) 0.0748(8) Uani d . 1 . . C C18 0.7778(3) 1.1712(3) 0.1213(3) 0.0668(8) Uani d . 1 . . C C19 0.7855(2) 0.7367(2) 0.3483(2) 0.0498(6) Uani d . 1 . . C C20 0.8495(2) 0.6190(3) 0.3210(3) 0.0624(7) Uani d . 1 . . C C21 0.9568(3) 0.6250(3) 0.4212(3) 0.0706(8) Uani d . 1 . . C C22 0.9975(3) 0.7458(3) 0.5419(3) 0.0683(8) Uani d . 1 . . C C23 0.9328(2) 0.8701(2) 0.5708(2) 0.0542(6) Uani d . 1 . . C C24 0.8232(2) 0.8648(2) 0.4706(2) 0.0485(6) Uani d . 1 . . C C25 0.7611(3) 0.9889(3) 0.4968(3) 0.0621(7) Uani d . 1 . . C C26 0.8075(3) 1.1115(3) 0.6154(3) 0.0763(8) Uani d . 1 . . C C27 0.9148(4) 1.1178(3) 0.7154(3) 0.0854(9) Uani d . 1 . . C C28 0.9749(3) 0.9996(3) 0.6929(3) 0.0746(8) Uani d . 1 . . C H2 0.259(2) 0.6063(18) 0.0161(19) 0.052(6) Uiso d . 1 . . H H5 0.5742(19) 0.6033(17) 0.3686(18) 0.044(6) Uiso d . 1 . . H H10 0.401(2) 0.940(2) 0.261(2) 0.080(8) Uiso d . 1 . . H H11 0.467(2) 1.184(2) 0.369(2) 0.076(9) Uiso d . 1 . . H H12 0.637(2) 1.296(2) 0.315(2) 0.084(8) Uiso d . 1 . . H H15 0.671(2) 0.769(2) -0.0599(19) 0.062(6) Uiso d . 1 . . H H16 0.836(3) 0.876(3) -0.131(3) 0.107(10) Uiso d . 1 . . H H17 0.903(3) 1.135(3) -0.005(3) 0.113(10) Uiso d . 1 . . H H18 0.801(2) 1.273(2) 0.166(2) 0.067(7) Uiso d . 1 . . H H20 0.822(2) 0.529(2) 0.226(2) 0.085(7) Uiso d . 1 . . H H21 0.993(3) 0.540(2) 0.400(2) 0.089(9) Uiso d . 1 . . H H22 1.062(2) 0.756(2) 0.611(2) 0.064(7) Uiso d . 1 . . H H25 0.700(2) 0.986(2) 0.429(2) 0.072(8) Uiso d . 1 . . H H26 0.761(3) 1.192(3) 0.622(3) 0.109(11) Uiso d . 1 . . H H27 0.950(3) 1.206(3) 0.792(2) 0.090(8) Uiso d . 1 . . H H28 1.045(3) 0.999(2) 0.753(2) 0.084(9) Uiso d . 1 . . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0586(10) 0.0491(9) 0.0480(9) -0.0042(7) 0.0007(7) 0.0289(7) O2 0.0465(10) 0.0669(10) 0.0621(10) -0.0082(7) -0.0046(8) 0.0417(8) N1 0.0576(14) 0.0731(14) 0.1016(17) -0.0088(11) 0.0069(12) 0.0445(12) N2 0.0949(17) 0.0954(16) 0.0957(16) 0.0100(12) 0.0330(14) 0.0661(14) C1 0.0499(14) 0.0439(12) 0.0451(12) -0.0003(10) 0.0023(11) 0.0248(10) C2 0.0506(15) 0.0437(12) 0.0457(13) 0.0007(11) -0.0022(12) 0.0217(11) C3 0.0494(14) 0.0372(11) 0.0504(13) 0.0007(10) 0.0079(11) 0.0174(10) C4 0.0523(15) 0.0405(12) 0.0490(13) 0.0014(10) 0.0095(12) 0.0233(10) C5 0.0535(16) 0.0486(13) 0.0492(14) 0.0037(11) 0.0019(12) 0.0290(12) C6 0.0570(16) 0.0466(13) 0.0707(17) -0.0002(12) 0.0094(14) 0.0267(12) C7 0.0604(16) 0.0561(14) 0.0618(15) 0.0066(11) 0.0165(13) 0.0319(13) C8 0.0438(14) 0.0435(12) 0.0489(13) 0.0002(10) 0.0020(11) 0.0235(10) C9 0.0468(14) 0.0431(12) 0.0508(13) 0.0039(11) -0.0028(12) 0.0262(11) C10 0.0592(17) 0.0633(17) 0.0649(17) 0.0135(14) 0.0174(14) 0.0356(14) C11 0.081(2) 0.0579(18) 0.0737(19) 0.0294(16) 0.0189(17) 0.0260(15) C12 0.075(2) 0.0452(16) 0.0741(19) 0.0097(14) -0.0028(16) 0.0290(15) C13 0.0537(15) 0.0444(13) 0.0526(14) 0.0022(12) -0.0057(12) 0.0271(12) C14 0.0400(13) 0.0458(13) 0.0503(13) 0.0018(10) -0.0032(11) 0.0296(11) C15 0.0545(16) 0.0571(16) 0.0574(16) 0.0044(13) 0.0070(13) 0.0312(14) C16 0.0652(18) 0.0792(19) 0.0687(18) 0.0017(15) 0.0135(15) 0.0410(16) C17 0.066(2) 0.081(2) 0.082(2) -0.0123(16) 0.0019(17) 0.0503(18) C18 0.0666(18) 0.0530(17) 0.0779(19) -0.0105(15) -0.0121(16) 0.0399(16) C19 0.0407(13) 0.0593(14) 0.0539(14) -0.0010(11) 0.0015(11) 0.0345(12) C20 0.0662(17) 0.0551(15) 0.0640(17) 0.0061(13) 0.0040(14) 0.0299(14) C21 0.0711(19) 0.0656(18) 0.081(2) 0.0193(15) 0.0093(16) 0.0411(17) C22 0.0524(17) 0.088(2) 0.0697(19) 0.0077(15) -0.0021(15) 0.0472(17) C23 0.0467(14) 0.0628(15) 0.0505(14) -0.0069(12) 0.0031(12) 0.0288(12) C24 0.0421(13) 0.0555(14) 0.0503(13) 0.0009(11) 0.0110(11) 0.0274(12) C25 0.0624(18) 0.0632(17) 0.0654(18) 0.0099(14) 0.0205(15) 0.0320(15) C26 0.093(2) 0.068(2) 0.069(2) 0.0127(17) 0.0336(18) 0.0278(18) C27 0.108(3) 0.071(2) 0.0592(19) -0.013(2) 0.0270(19) 0.0155(17) C28 0.070(2) 0.088(2) 0.0568(18) -0.0106(17) 0.0057(16) 0.0324(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.379(2) yes O1 C9 . 1.415(2) yes O2 C8 . 1.363(2) yes O2 C19 . 1.409(2) yes N1 C6 . 1.128(3) yes N2 C7 . 1.130(3) yes C1 C2 . 1.378(3) ? C1 C8 . 1.401(3) ? C2 C3 . 1.386(3) ? C2 H2 . 0.951(19) ? C3 C4 . 1.391(3) ? C3 C6 . 1.439(3) ? C4 C5 . 1.391(3) ? C4 C7 . 1.441(3) ? C5 C8 . 1.377(3) ? C5 H5 . 0.913(18) ? C9 C10 . 1.348(3) ? C9 C14 . 1.416(3) ? C10 C11 . 1.410(3) ? C10 H10 . 0.96(2) ? C11 C12 . 1.356(3) ? C11 H11 . 0.92(2) ? C12 C13 . 1.400(3) ? C12 H12 . 0.95(2) ? C13 C14 . 1.410(3) ? C13 C18 . 1.420(3) ? C14 C15 . 1.389(3) ? C15 C16 . 1.375(3) ? C15 H15 . 0.976(18) ? C16 C17 . 1.398(3) ? C16 H16 . 0.99(2) ? C17 C18 . 1.343(3) ? C17 H17 . 0.95(3) ? C18 H18 . 0.948(19) ? C19 C20 . 1.358(3) ? C19 C24 . 1.391(3) ? C20 C21 . 1.397(3) ? C20 H20 . 1.03(2) ? C21 C22 . 1.347(3) ? C21 H21 . 0.92(2) ? C22 C23 . 1.419(3) ? C22 H22 . 0.88(2) ? C23 C28 . 1.401(3) ? C23 C24 . 1.414(3) ? C24 C25 . 1.407(3) ? C25 C26 . 1.349(3) ? C25 H25 . 0.88(2) ? C26 C27 . 1.395(4) ? C26 H26 . 0.97(3) ? C27 C28 . 1.349(4) ? C27 H27 . 0.93(2) ? C28 H28 . 0.90(2) ? _cod_database_code 2202504