#------------------------------------------------------------------------------ #$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $ #$Revision: 26029 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2014635.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_2014635 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2005 _journal_volume 61 _journal_page_first o35 _journal_page_last o37 _publ_section_title ; 4'-Hydroxybiphenyl-4-carbonitrile ; loop_ _publ_author_name 'Britton, Doyle' _chemical_formula_moiety 'C13 H9 N O' _chemical_formula_sum 'C13 H9 N O' _chemical_formula_iupac 'C13 H9 N O' _chemical_formula_weight 195.21 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'C -1' _symmetry_space_group_name_Hall '-C 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, y+1/2, z' '-x, -y, -z' '-x+1/2, -y+1/2, -z' _cell_length_a 12.936(3) _cell_length_b 33.696(8) _cell_length_c 10.604(3) _cell_angle_alpha 90.350(10) _cell_angle_beta 120.670(10) _cell_angle_gamma 89.600(10) _cell_volume 3975.5(17) _cell_formula_units_Z 16 _cell_measurement_temperature 174(2) _exptl_crystal_density_diffrn 1.305 _diffrn_ambient_temperature 174(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 C1A 0.98745(17) 0.12082(6) 0.0517(2) 0.0366(4) Uani d . 1 . . C C2A 0.94088(19) 0.08990(6) 0.0936(2) 0.0447(5) Uani d . 1 . . C H2A 0.9881 0.0669 0.1388 0.054 Uiso calc R 1 . . H C3A 0.82539(18) 0.09281(6) 0.0692(2) 0.0411(5) Uani d . 1 . . C H3A 0.7943 0.0717 0.0988 0.049 Uiso calc R 1 . . H C4A 0.75349(16) 0.12605(5) 0.0022(2) 0.0310(4) Uani d . 1 . . C C5A 0.80250(17) 0.15683(5) -0.0392(2) 0.0350(4) Uani d . 1 . . C H5A 0.7552 0.1797 -0.0854 0.042 Uiso calc R 1 . . H C6A 0.91787(18) 0.15447(6) -0.0143(2) 0.0383(4) Uani d . 1 . . C H6A 0.9498 0.1758 -0.0420 0.046 Uiso calc R 1 . . H C7A 0.62863(16) 0.12885(5) -0.0268(2) 0.0308(4) Uani d . 1 . . C C8A 0.59531(17) 0.11127(5) 0.0666(2) 0.0320(4) Uani d . 1 . . C H8A 0.6539 0.0971 0.1502 0.038 Uiso calc R 1 . . H C9A 0.47871(17) 0.11411(5) 0.0399(2) 0.0334(4) Uani d . 1 . . C H9A 0.4581 0.1020 0.1049 0.040 Uiso calc R 1 . . H C10A 0.39205(16) 0.13470(5) -0.0823(2) 0.0336(4) Uani d . 1 . . C C11A 0.42366(17) 0.15250(6) -0.1756(2) 0.0360(4) Uani d . 1 . . C H11A 0.3650 0.1667 -0.2589 0.043 Uiso calc R 1 . . H C12A 0.53984(17) 0.14960(5) -0.1480(2) 0.0344(4) Uani d . 1 . . C H12A 0.5600 0.1620 -0.2128 0.041 Uiso calc R 1 . . H C13A 1.10525(19) 0.11767(6) 0.0696(2) 0.0422(5) Uani d . 1 . . C N14A 1.19775(17) 0.11542(6) 0.0797(2) 0.0544(5) Uani d . 1 . . N O15A 0.27569(13) 0.13834(5) -0.11598(17) 0.0448(4) Uani d . 1 . . O H15A 0.258(3) 0.1273(9) -0.053(3) 0.080(10) Uiso d . 1 . . H C1B 0.34477(17) 0.24397(6) 0.1938(2) 0.0357(4) Uani d . 1 . . C C2B 0.39675(18) 0.21186(6) 0.1629(2) 0.0374(4) Uani d . 1 . . C H2B 0.3544 0.1876 0.1287 0.045 Uiso calc R 1 . . H C3B 0.51035(17) 0.21554(6) 0.1823(2) 0.0342(4) Uani d . 1 . . C H3B 0.5450 0.1937 0.1598 0.041 Uiso calc R 1 . . H C4B 0.57512(16) 0.25072(5) 0.23438(19) 0.0298(4) Uani d . 1 . . C C5B 0.52048(17) 0.28283(6) 0.2635(2) 0.0350(4) Uani d . 1 . . C H5B 0.5629 0.3071 0.2979 0.042 Uiso calc R 1 . . H C6B 0.40679(18) 0.27986(6) 0.2432(2) 0.0383(4) Uani d . 1 . . C H6B 0.3709 0.3019 0.2626 0.046 Uiso calc R 1 . . H C7B 0.69957(16) 0.25411(5) 0.2629(2) 0.0301(4) Uani d . 1 . . C C8B 0.73681(18) 0.23553(5) 0.1745(2) 0.0346(4) Uani d . 1 . . C H8B 0.6810 0.2201 0.0929 0.042 Uiso calc R 1 . . H C9B 0.85427(18) 0.23923(6) 0.2039(2) 0.0359(4) Uani d . 1 . . C H9B 0.8774 0.2270 0.1411 0.043 Uiso calc R 1 . . H C10B 0.93750(17) 0.26085(5) 0.3250(2) 0.0345(4) Uani d . 1 . . C C11B 0.90259(18) 0.27900(5) 0.4155(2) 0.0356(4) Uani d . 1 . . C H11B 0.9593 0.2937 0.4989 0.043 Uiso calc R 1 . . H C12B 0.78543(17) 0.27570(5) 0.3841(2) 0.0334(4) Uani d . 1 . . C H12B 0.7625 0.2884 0.4463 0.040 Uiso calc R 1 . . H C13B 0.22787(19) 0.24024(6) 0.1782(2) 0.0412(5) Uani d . 1 . . C N14B 0.13566(17) 0.23775(6) 0.1682(2) 0.0517(5) Uani d . 1 . . N O15B 1.05447(13) 0.26516(5) 0.36076(18) 0.0464(4) Uani d . 1 . . O H15B 1.070(3) 0.2544(9) 0.292(3) 0.082(10) Uiso d . 1 . . H C1C 0.25715(17) 0.36860(6) 0.5480(2) 0.0362(4) Uani d . 1 . . C C2C 0.33740(19) 0.33700(6) 0.5826(2) 0.0435(5) Uani d . 1 . . C H2C 0.3262 0.3131 0.6211 0.052 Uiso calc R 1 . . H C3C 0.43298(19) 0.34073(6) 0.5603(2) 0.0408(5) Uani d . 1 . . C H3C 0.4881 0.3193 0.5855 0.049 Uiso calc R 1 . . H C4C 0.45071(17) 0.37520(5) 0.5019(2) 0.0334(4) Uani d . 1 . . C C5C 0.36890(18) 0.40654(6) 0.4672(2) 0.0374(4) Uani d . 1 . . C H5C 0.3792 0.4303 0.4271 0.045 Uiso calc R 1 . . H C6C 0.27332(18) 0.40338(6) 0.4904(2) 0.0385(5) Uani d . 1 . . C H6C 0.2189 0.4249 0.4671 0.046 Uiso calc R 1 . . H C7C 0.55200(17) 0.37875(5) 0.4750(2) 0.0320(4) Uani d . 1 . . C C8C 0.66464(17) 0.36213(6) 0.5691(2) 0.0353(4) Uani d . 1 . . C H8C 0.6772 0.3480 0.6530 0.042 Uiso calc R 1 . . H C9C 0.75901(18) 0.36586(6) 0.5428(2) 0.0365(4) Uani d . 1 . . C H9C 0.8353 0.3545 0.6088 0.044 Uiso calc R 1 . . H C10C 0.74152(17) 0.38616(6) 0.4201(2) 0.0357(4) Uani d . 1 . . C C11C 0.63037(18) 0.40299(6) 0.3251(2) 0.0378(4) Uani d . 1 . . C H11C 0.6182 0.4170 0.2410 0.045 Uiso calc R 1 . . H C12C 0.53746(18) 0.39950(5) 0.3524(2) 0.0355(4) Uani d . 1 . . C H12C 0.4620 0.4114 0.2869 0.043 Uiso calc R 1 . . H C13C 0.15359(19) 0.36513(6) 0.5643(2) 0.0412(5) Uani d . 1 . . C N14C 0.06959(17) 0.36321(6) 0.5746(2) 0.0514(5) Uani d . 1 . . N O15C 0.83044(14) 0.39063(5) 0.38768(18) 0.0475(4) Uani d . 1 . . O H15C 0.900(2) 0.3789(8) 0.457(3) 0.072(9) Uiso d . 1 . . H C1D 1.11473(18) 0.49599(6) 0.6949(2) 0.0392(5) Uani d . 1 . . C C2D 1.03733(19) 0.46372(6) 0.6595(2) 0.0422(5) Uani d . 1 . . C H2D 1.0521 0.4398 0.6231 0.051 Uiso calc R 1 . . H C3D 0.93916(18) 0.46674(6) 0.6778(2) 0.0391(5) Uani d . 1 . . C H3D 0.8862 0.4448 0.6523 0.047 Uiso calc R 1 . . H C4D 0.91615(17) 0.50113(5) 0.7327(2) 0.0340(4) Uani d . 1 . . C C5D 0.99403(18) 0.53363(6) 0.7654(2) 0.0384(5) Uani d . 1 . . C H5D 0.9789 0.5576 0.8010 0.046 Uiso calc R 1 . . H C6D 1.09171(18) 0.53120(6) 0.7465(2) 0.0407(5) Uani d . 1 . . C H6D 1.1431 0.5534 0.7685 0.049 Uiso calc R 1 . . H C7D 0.81565(17) 0.50391(5) 0.7615(2) 0.0341(4) Uani d . 1 . . C C8D 0.70321(18) 0.48708(6) 0.6693(2) 0.0383(4) Uani d . 1 . . C H8D 0.6897 0.4727 0.5849 0.046 Uiso calc R 1 . . H C9D 0.61057(18) 0.49103(6) 0.6988(2) 0.0421(5) Uani d . 1 . . C H9D 0.5342 0.4797 0.6343 0.050 Uiso calc R 1 . . H C10D 0.62971(19) 0.51157(6) 0.8228(2) 0.0402(5) Uani d . 1 . . C C11D 0.74151(19) 0.52809(6) 0.9170(2) 0.0416(5) Uani d . 1 . . C H11D 0.7551 0.5420 1.0023 0.050 Uiso calc R 1 . . H C12D 0.83264(18) 0.52422(6) 0.8864(2) 0.0396(5) Uani d . 1 . . C H12D 0.9088 0.5356 0.9516 0.047 Uiso calc R 1 . . H C13D 1.2198(2) 0.49270(7) 0.6818(2) 0.0461(5) Uani d . 1 . . C N14D 1.30501(19) 0.49029(6) 0.6741(2) 0.0592(5) Uani d . 1 . . N O15D 0.54339(16) 0.51658(5) 0.8601(2) 0.0536(4) Uani d . 1 . . O H15D 0.471(2) 0.5073(7) 0.784(3) 0.058(8) 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 C1A 0.0357(10) 0.0432(11) 0.0328(10) -0.0024(8) 0.0189(9) -0.0040(8) C2A 0.0409(12) 0.0405(12) 0.0521(13) 0.0063(9) 0.0233(10) 0.0112(10) C3A 0.0393(11) 0.0358(11) 0.0481(12) 0.0008(9) 0.0221(10) 0.0112(9) C4A 0.0353(10) 0.0283(9) 0.0290(9) -0.0036(7) 0.0160(8) -0.0011(7) C5A 0.0408(11) 0.0282(10) 0.0359(10) 0.0000(8) 0.0195(9) 0.0033(8) C6A 0.0441(12) 0.0361(11) 0.0406(11) -0.0055(9) 0.0259(10) 0.0011(8) C7A 0.0338(10) 0.0244(9) 0.0315(9) -0.0034(7) 0.0148(8) -0.0030(7) C8A 0.0355(10) 0.0275(9) 0.0291(9) -0.0017(7) 0.0135(8) 0.0011(7) C9A 0.0392(10) 0.0293(9) 0.0336(10) -0.0056(8) 0.0198(9) -0.0035(8) C10A 0.0319(10) 0.0306(10) 0.0347(10) -0.0019(8) 0.0145(8) -0.0077(8) C11A 0.0375(11) 0.0333(10) 0.0311(10) 0.0031(8) 0.0131(8) 0.0021(8) C12A 0.0404(11) 0.0298(10) 0.0322(10) -0.0016(8) 0.0179(9) 0.0026(8) C13A 0.0416(12) 0.0488(12) 0.0371(11) -0.0026(9) 0.0208(9) -0.0047(9) N14A 0.0443(11) 0.0699(14) 0.0553(12) -0.0017(9) 0.0300(10) -0.0078(10) O15A 0.0351(8) 0.0503(9) 0.0484(9) 0.0033(6) 0.0209(7) -0.0002(7) C1B 0.0341(10) 0.0423(11) 0.0310(10) 0.0018(8) 0.0168(8) 0.0053(8) C2B 0.0400(11) 0.0349(10) 0.0356(10) -0.0060(8) 0.0180(9) -0.0033(8) C3B 0.0394(11) 0.0298(10) 0.0338(10) 0.0014(8) 0.0189(9) -0.0016(8) C4B 0.0369(10) 0.0288(9) 0.0236(9) 0.0013(7) 0.0152(8) 0.0034(7) C5B 0.0403(11) 0.0275(9) 0.0386(11) -0.0006(8) 0.0211(9) -0.0007(8) C6B 0.0434(11) 0.0344(10) 0.0402(11) 0.0060(8) 0.0236(9) 0.0020(8) C7B 0.0365(10) 0.0237(9) 0.0305(9) 0.0023(7) 0.0174(8) 0.0049(7) C8B 0.0415(11) 0.0291(9) 0.0331(10) 0.0012(8) 0.0189(9) 0.0001(8) C9B 0.0440(11) 0.0327(10) 0.0373(10) 0.0077(8) 0.0253(9) 0.0037(8) C10B 0.0363(10) 0.0299(10) 0.0387(11) 0.0048(8) 0.0201(9) 0.0112(8) C11B 0.0398(11) 0.0303(10) 0.0349(10) -0.0034(8) 0.0177(9) 0.0016(8) C12B 0.0415(11) 0.0293(9) 0.0338(10) -0.0013(8) 0.0225(9) -0.0016(8) C13B 0.0424(12) 0.0468(12) 0.0362(11) 0.0012(9) 0.0214(9) 0.0052(9) N14B 0.0456(11) 0.0622(13) 0.0556(12) 0.0006(9) 0.0319(10) 0.0094(10) O15B 0.0388(8) 0.0493(9) 0.0558(10) 0.0033(7) 0.0276(8) 0.0082(7) C1C 0.0354(10) 0.0372(11) 0.0319(10) -0.0002(8) 0.0143(8) -0.0019(8) C2C 0.0508(13) 0.0361(11) 0.0465(12) 0.0063(9) 0.0268(10) 0.0115(9) C3C 0.0461(12) 0.0348(11) 0.0436(11) 0.0125(9) 0.0245(10) 0.0107(9) C4C 0.0368(10) 0.0302(10) 0.0282(9) 0.0024(8) 0.0131(8) -0.0003(7) C5C 0.0411(11) 0.0271(10) 0.0406(11) 0.0015(8) 0.0183(9) 0.0025(8) C6C 0.0364(11) 0.0312(10) 0.0415(11) 0.0043(8) 0.0152(9) -0.0001(8) C7C 0.0370(10) 0.0270(9) 0.0287(9) 0.0002(7) 0.0143(8) -0.0027(7) C8C 0.0411(11) 0.0323(10) 0.0285(9) 0.0029(8) 0.0149(8) 0.0020(8) C9C 0.0352(10) 0.0334(10) 0.0340(10) 0.0033(8) 0.0125(8) 0.0001(8) C10C 0.0373(11) 0.0316(10) 0.0375(11) -0.0058(8) 0.0187(9) -0.0053(8) C11C 0.0438(11) 0.0335(10) 0.0328(10) -0.0025(8) 0.0171(9) 0.0018(8) C12C 0.0379(10) 0.0291(10) 0.0334(10) 0.0023(8) 0.0137(8) 0.0032(8) C13C 0.0417(12) 0.0370(11) 0.0405(11) -0.0012(9) 0.0178(10) -0.0021(9) N14C 0.0429(11) 0.0485(11) 0.0644(13) -0.0035(8) 0.0284(10) -0.0051(9) O15C 0.0429(9) 0.0526(9) 0.0499(9) -0.0024(7) 0.0257(8) 0.0030(7) C1D 0.0397(11) 0.0404(11) 0.0342(10) -0.0015(9) 0.0164(9) 0.0006(8) C2D 0.0482(12) 0.0343(11) 0.0419(12) -0.0014(9) 0.0213(10) -0.0039(9) C3D 0.0450(12) 0.0286(10) 0.0392(11) -0.0054(8) 0.0183(9) -0.0020(8) C4D 0.0356(10) 0.0288(9) 0.0284(9) 0.0002(8) 0.0096(8) 0.0029(7) C5D 0.0421(11) 0.0287(10) 0.0394(11) -0.0024(8) 0.0170(9) -0.0033(8) C6D 0.0423(11) 0.0354(11) 0.0392(11) -0.0082(9) 0.0170(9) -0.0017(8) C7D 0.0369(10) 0.0253(9) 0.0335(10) 0.0007(8) 0.0132(8) 0.0053(7) C8D 0.0425(11) 0.0320(10) 0.0345(10) -0.0049(8) 0.0151(9) 0.0033(8) C9D 0.0374(11) 0.0369(11) 0.0421(12) -0.0046(9) 0.0130(9) 0.0075(9) C10D 0.0420(11) 0.0330(10) 0.0469(12) 0.0067(8) 0.0236(10) 0.0150(9) C11D 0.0477(12) 0.0359(11) 0.0389(11) 0.0055(9) 0.0204(10) 0.0034(9) C12D 0.0387(11) 0.0328(10) 0.0391(11) 0.0003(8) 0.0139(9) 0.0004(8) C13D 0.0477(13) 0.0460(13) 0.0431(12) -0.0033(10) 0.0220(10) -0.0014(10) N14D 0.0547(13) 0.0660(14) 0.0639(14) -0.0049(10) 0.0353(11) -0.0072(11) O15D 0.0501(10) 0.0534(10) 0.0644(11) 0.0050(8) 0.0342(9) 0.0120(8) 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 C1A C2A . 1.391(3) ? C1A C6A . 1.392(3) ? C1A C13A . 1.439(3) ? C2A C3A . 1.383(3) ? C2A H2A . 0.9500 ? C3A C4A . 1.395(3) ? C3A H3A . 0.9500 ? C4A C5A . 1.403(2) ? C4A C7A . 1.485(3) ? C5A C6A . 1.378(3) ? C5A H5A . 0.9500 ? C6A H6A . 0.9500 ? C7A C12A . 1.398(3) ? C7A C8A . 1.402(3) ? C8A C9A . 1.388(3) ? C8A H8A . 0.9500 ? C9A C10A . 1.391(3) ? C9A H9A . 0.9500 ? C10A O15A . 1.363(2) ? C10A C11A . 1.389(3) ? C11A C12A . 1.379(3) ? C11A H11A . 0.9500 ? C12A H12A . 0.9500 ? C13A N14A . 1.148(3) ? O15A H15A . 0.89(3) ? C1B C2B . 1.393(3) ? C1B C6B . 1.399(3) ? C1B C13B . 1.441(3) ? C2B C3B . 1.382(3) ? C2B H2B . 0.9500 ? C3B C4B . 1.395(3) ? C3B H3B . 0.9500 ? C4B C5B . 1.405(3) ? C4B C7B . 1.484(3) ? C5B C6B . 1.378(3) ? C5B H5B . 0.9500 ? C6B H6B . 0.9500 ? C7B C8B . 1.397(3) ? C7B C12B . 1.399(3) ? C8B C9B . 1.393(3) ? C8B H8B . 0.9500 ? C9B C10B . 1.388(3) ? C9B H9B . 0.9500 ? C10B O15B . 1.368(2) ? C10B C11B . 1.390(3) ? C11B C12B . 1.381(3) ? C11B H11B . 0.9500 ? C12B H12B . 0.9500 ? C13B N14B . 1.146(3) ? O15B H15B . 0.92(3) ? C1C C6C . 1.390(3) ? C1C C2C . 1.395(3) ? C1C C13C . 1.441(3) ? C2C C3C . 1.378(3) ? C2C H2C . 0.9500 ? C3C C4C . 1.394(3) ? C3C H3C . 0.9500 ? C4C C5C . 1.401(3) ? C4C C7C . 1.482(3) ? C5C C6C . 1.383(3) ? C5C H5C . 0.9500 ? C6C H6C . 0.9500 ? C7C C8C . 1.395(3) ? C7C C12C . 1.405(3) ? C8C C9C . 1.391(3) ? C8C H8C . 0.9500 ? C9C C10C . 1.386(3) ? C9C H9C . 0.9500 ? C10C O15C . 1.368(2) ? C10C C11C . 1.386(3) ? C11C C12C . 1.378(3) ? C11C H11C . 0.9500 ? C12C H12C . 0.9500 ? C13C N14C . 1.148(3) ? O15C H15C . 0.91(3) ? C1D C2D . 1.397(3) ? C1D C6D . 1.396(3) ? C1D C13D . 1.439(3) ? C2D C3D . 1.382(3) ? C2D H2D . 0.9500 ? C3D C4D . 1.391(3) ? C3D H3D . 0.9500 ? C4D C5D . 1.410(3) ? C4D C7D . 1.481(3) ? C5D C6D . 1.378(3) ? C5D H5D . 0.9500 ? C6D H6D . 0.9500 ? C7D C8D . 1.396(3) ? C7D C12D . 1.402(3) ? C8D C9D . 1.390(3) ? C8D H8D . 0.9500 ? C9D C10D . 1.388(3) ? C9D H9D . 0.9500 ? C10D O15D . 1.371(3) ? C10D C11D . 1.389(3) ? C11D C12D . 1.378(3) ? C11D H11D . 0.9500 ? C12D H12D . 0.9500 ? C13D N14D . 1.148(3) ? O15D H15D . 0.92(3) ? _cod_database_code 2014635