Crystal structure of adamantylammonium bicarbonate, [C10H18NJHCO3

Abstract

C11H19NO3, orthorhombic, P212121 (no. 19), a = 6.3919(1) A, b = 7.3659(2) A, c = 22.8347(5) A, V = 1075.1 A, Z = 4, Rgt(F) = 0.044, wRref(F) = 0.129, T = 296 K. Source of material Reagents and solvents usedwere of commercially available quality. Adamantaneamine was not a primary reactant in this investigation. It was produced from decomposition of theN-2-hydroxy3-methoxy-benzaldehyde-1-aminoadamanantane. The latter was synthesized according to [1]. NaHCO3 (2 mmol) and N-2hydroxy-3-methoxybenzaldehyde-1-aminoadamanantane (2 mmol) were dissolved in methanol (30 ml) solution and the mixture was stirred for 8 h at room temperature. The yellow solution was kept aside, and the yellow crystal was obtained after several days. Experimental details The crystal structurewas solved by directmethods and successive Fourier difference syntheses. The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [d(Caliphatic—H) = 0.97(2) A and d(N—H) = 0.86 A, Uiso(H) = 1.2 Ueq(C)]. The H atoms bonded to O atoms were located in a difference Fourier maps and refined with O—H distance restraints of 0.85(2) A and Uiso(H) = 1.5 Ueq(O). Discussion Adamantane has a highly-symmetric and steady structure. Adamantaneamine has an obvious effect on controlling the exuviating the influenzaA virus. Especially, it can be used to prevent virus going into host cells and influenza A2 in asia. In addition it can alleviate the Parkinson symptom [2]. The title crystal structure is formed by adamantaneamine cations and bicarbonate anions. All the C—C bonds (C1-C10) are in the range of 1.516(3)A 1.535(3)A in the adamantyl group, with C$ C$C bond angles of 108.7(2)°110.3(2)°, which is consistent with diamond-like unit. TheC—Nbond length is 1.503(3)A. The bicarbonate anion and the adamantaneamine cation are connected with each otherwith hydrogen bonds. These hydrogen bonds contribute to the formation of a two-dimensional network. Z. Kristallogr. NCS 224 (2009) 69-70 / DOI 10.1524/ncrs.2009.0028 69 © by Oldenbourg Wissenschaftsverlag, Munchen Crystal: yellow block, size 0.089 × 0.108 × 0.297 mm Wavelength: Mo K0 radiation (0.71073 A) %: 0.95 cm Diffractometer, scan mode: Bruker APEX-II, 2 2max: 49.98° N(hkl)measured, N(hkl)unique: 4726, 1905 Criterion for Iobs, N(hkl)gt: Iobs > 2 !(Iobs), 1593 N(param)refined: 145 Programs: SHELXS-97 [3], SHELDXL-97 [4], SHELXTL [5] Table 1. Data collection and handling. H(3D) 4a 0.0607 0.0226 0.3060 0.086 H(2A) 4a $0.1910 0.1037 0.1604 0.050 H(2B) 4a $0.0512 $0.0423 0.1919 0.050 H(3A) 4a 0.3342 $0.0594 0.1702 0.051 H(3B) 4a 0.4354 0.0766 0.1253 0.051 H(4A) 4a 0.2103 0.3116 0.0755 0.049 H(4B) 4a $0.0306 0.3207 0.0891 0.049 H(5A) 4a 0.2046 $0.1062 $0.0045 0.057 H(5B) 4a 0.3558 0.0473 0.0177 0.057 H(6A) 4a 0.3860 $0.2097 0.0794 0.054 H(7A) 4a 0.0421 $0.3222 0.0671 0.057 H(7B) 4a 0.0921 $0.3052 0.1343 0.057 H(8A) 4a $0.2406 $0.1817 0.1150 0.053 H(9A) 4a $0.1792 $0.0873 0.0173 0.057 H(9B) 4a $0.2682 0.0768 0.0535 0.057 H(10A) 4a 0.0222 0.1737 $0.0020 0.052 H(1A) 4a 0.057(5) 0.348(4) 0.201(1) 0.053 H(1B) 4a 0.282(4) 0.338(4) 0.181(1) 0.053 H(1C) 4a 0.170(4) 0.197(4) 0.228(1) 0.053 Table 2. Atomic coordinates and displacement parameters (in A). Atom Site x y z Uiso