Crystal structure of 3′-benzyloxy-2′-naphthyl-l-bromo-2-naphthoate, C28H19Br3
| Autor: | E.-M. Peters, Karl Peters, A. Wuzik, R.-M. Pfeifer, Gerhard Bringmann |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2003 |
| Předmět: |
Bromine
Crystallography Bicyclic molecule Stereochemistry Substituent chemistry.chemical_element Crystal structure Dihedral angle Condensed Matter Physics Inorganic Chemistry chemistry.chemical_compound chemistry QD901-999 Benzyl group General Materials Science Single crystal Monoclinic crystal system |
| Zdroj: | Zeitschrift für Kristallographie-New Crystal Structures, Vol 218, Iss JG, Pp 221-222 (2003) |
| ISSN: | 2197-4578 1433-7266 |
| Popis: | C28H19BrO3, monoclinic, P121/c1 (No. 14), a = 13.769(1) A, b = 19.058(2) A, c = 8.716(1) A, = 107.964(6)°, V = 2175.7 A, Z = 4, Rgt(F) = 0.059, wRref(F) = 0.164, T = 293 K. Source of material The title compound was prepared according to [1] by esterification of the commercially available -1-bromonaphthoic acid [2] with the likewise known [3] 3-benzyloxy-2-naphthol. It is a useful intermediate in the synthesis of a twofold lactone bridged terayl [1]. Discussion Although the title compound is a useful synthetic precursor for the intramolecular biaryl coupling to link the bromine-bearing C-atom (C11) with C13 to give a six-membered lactone ring [1], it adopts a quite different conformation in the crystal, with C13 far away from the bromine (6.26 A). The bromine is, in turn, quite close to the aromatic ring of the benzyl group, with ca. 4.50 A distance as an average. Likewise remarkable is the non-coplanar array of the carboxyl unit (O1–C1–O12) with the naphthalene nucleus, with a significant dihedral angle between these two planes (58.1°), apparently due to the bulky bromine substituent at C11. Z. Kristallogr. NCS 218 (2003) 209–210 209 © by Oldenbourg Wissenschaftsverlag, Munchen Crystal: pale yellow plate, size 0.1 × 0.95 × 1.05 mm Wavelength: Mo K radiation (0.71073 A) : 19.18 cm Diffractometer, scan mode: Bruker AXS P4, 2 max: 55° N(hkl)measured, N(hkl)unique: 4866, 4593 Criterion for Iobs, N(hkl)gt: Iobs > 2 (Iobs), 3037 N(param)refined: 289 Program: SHELXTL [4] Table 1. Data collection and handling. H(3) 4e 0.4967 1.0220 0.3019 0.08 H(4) 4e 0.4214 1.0839 0.4565 0.08 H(6) 4e 0.2694 1.1172 0.5317 0.08 H(7) 4e 0.1008 1.1034 0.5058 0.08 H(8) 4e 0.0009 1.0273 0.3124 0.08 H(9) 4e 0.0718 0.9618 0.1547 0.08 H(13) 4e 0.6814 0.9326 0.1624 0.08 H(15) 4e 0.8556 0.9187 0.1273 0.08 H(16) 4e 0.9619 0.8617 0.0120 0.08 H(17) 4e 0.8995 0.7697 –0.1664 0.08 H(18) 4e 0.7372 0.7307 –0.2145 0.08 H(20) 4e 0.5691 0.7373 –0.1633 0.08 H(22A) 4e 0.4562 0.6817 –0.0682 0.08 H(22B) 4e 0.3905 0.7234 –0.2208 0.08 H(24) 4e 0.2105 0.7534 –0.2425 0.08 H(25) 4e 0.0637 0.7160 –0.1860 0.08 H(26) 4e 0.0779 0.6322 0.0130 0.08 H(27) 4e 0.2329 0.5887 0.1558 0.08 H(28) 4e 0.3764 0.6279 0.1057 0.08 Table 2. Atomic coordinates and displacement parameters (in A). Atom Site x y z Uiso |
| Databáze: | OpenAIRE |
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