Crystal structure of 1,8-bis[4-(4-pentylcyclohexyl)phenyl]-10- methoxyanthracene, C49H60O

C49H60O, triclinic, P1 (no. 2), a = 9.110(2) Å, b = 10.615(2) Å, c = 20.583(4) Å, 1 = 100.94(3)°, / = 90.97(3)°, . = 93.65(3)°, V = 1949.5 Å, Z = 2, Rgt(F) = 0.083, wRref(F) = 0.169, T = 293 K. Source of material The target compound was synthesized by Suzuki coupling reaction with Pd(PPh3)4 as the catalyst [1]. A mixture of 1,8-diiodo10-methoxyanthracene (6 mmol) and 1-bromo-4-(4-pentylcyclohexyl)benzene (15 mmol) was dissolved in benzene solution, and then sodium carbonate (36 mmol) and Pd(PPh3)4 (0.4 mmol) were added gradually. After the mixture was stirred for 0.5 h, it was heated at reflux at 80 °C under nitrogen atmosphere for 30 h. The crude product was extracted with dichloromethane, and then purified by chromatogrfic method with petroleum ether/chloroform (3:1, v/v). By crystallization from solution of chloroform/methanol, single crystals suitable for X-ray crystallography were obtained. Elemental analysis — found: C, 88.50 %; H, 9.0. %; calculated for C49H60O1: C, 88.21 %; H, 9.09 %. H NMR data are available in the CIF. Experimental details The diffraction intensity is relatively weak, which may be a reason for the larger R values. Additional molecules of solvent were not found. Discussion The earlier interest in 1,8-diphenylanthracene and its derivatives arose from the expectation of the favored conformation of this molecule, having both phenyl rings approximately perpendicular to the plane of the anthracene system. Such a conformation offers the possibility of conferring unusual physical and chemical properties [2-4]. Recently, increasing attention has been paid to 1,8diphenylanthracene based compounds as particular chelating ligands to transition metal complexes with Pd(II), Rh(I), Re(I) [5-7]. The crystal structure of the title compound has two long alkyl chains at the side phenyl rings, which crystallized in a longneedle fashion. The dihedral angle between the side phenyl groups (C16-C21, C33-C38) and the anthracene group are 50.4° and 126.4°, respectively. These are a little smaller than the corresponding twist angles (55 56°) in 1,8-diphenylanthracene [4]. Some interatomic distances between the two tails are as following: d(C16···C33) = 5.143 Å; d(C22···C39) = 5.583 Å; d(C28···C45) = 5.452 Å; d(C32···C49) = 5.204 Å, respectively. The methoxyl group is outside the plane of anthracene ring (C1C14) and the bond angle C15−O1−C6 is 113°. In the unit cell, the two molecules are head-to-head and the anthracene rings are approximately parallel. Due to the steric hindrance of methoxyl group, there is nearly no %-% stacking interaction in neighboring molecules. 512 Z. Kristallogr. NCS 224 (2009) 512-514 / DOI 10.1524/ncrs.2009.0224 © by Oldenbourg Wissenschaftsverlag, München Crystal: yellow needle, size 0.20 × 0.22 × 0.25 mm Wavelength: Mo K1 radiation (0.71073 Å) ': 0.65 cm−1 Diffractometer, scan mode: Bruker P4, 3 2#max: 50° N(hkl)measured, N(hkl)unique: 10950, 6752 Criterion for Iobs, N(hkl)gt: Iobs > 2 "(Iobs), 3926 N(param)refined: 445 Programs: SHELXS-97 [8], SHELXL-97 [9], SHELXTL [10] Table 1. Data collection and handling. H(2A) 2i 0.5282 0.3815 0.4607 0.079 H(3A) 2i 0.7475 0.2802 0.4480 0.087 H(4A) 2i 0.8584 0.2443 0.3497 0.080 H(8A) 2i 0.8560 0.2597 0.1107 0.096 H(9A) 2i 0.7402 0.3051 0.0209 0.106 H(10A) 2i 0.5236 0.4083 0.0300 0.099 H(13A) 2i 0.4093 0.4426 0.2500 0.070 H(15A) 2i 1.1162 0.2895 0.2332 0.133 H(15B) 2i 1.0273 0.3868 0.2816 0.133 H(15C) 2i 1.0227 0.3877 0.2055 0.133 H(17A) 2i 0.2588 0.3402 0.4250 0.071 H(18A) 2i 0.0449 0.4395 0.4455 0.070 H(20A) 2i 0.2009 0.7223 0.3575 0.075 H(21A) 2i 0.4136 0.6220 0.3369 0.074 Table 2. Atomic coordinates and displacement parameters (in Å). Atom Site x y z Uiso