2-(1-Adamant­yl)-4-bromo­anisole at 123 K

Xiang-Wei Cheng

doi:10.1107/S1600536808016772

. 2008 Jun 7;64(Pt 7):o1212. doi: 10.1107/S1600536808016772

2-(1-Adamantyl)-4-bromoanisole at 123 K

Xiang-Wei Cheng ^a,^*

PMCID: PMC2961646 PMID: 21202851

Abstract

In the title compound [systematic name: 2-(1-adamantyl)-4-bromo-1-methoxybenzene], C₁₇H₂₁BrO, two weak intramolecular C—H⋯O hydrogen bonds influence the molecular conformation. The crystal packing exhibits C—H⋯π interactions, with a relatively short intermolecular C⋯Cg contact of 3.568 (5) Å, where Cg is the centroid of the benzene ring. The crystal studied exhibited inversion twinning.

Related literature

For related crystal structures, see: Nordman & Schmitkons (1965 ▶); Amoureux et al. (1980 ▶); Amoureux & Bee (1980 ▶); Pouwer et al. (2007 ▶). For general background, see: Chomienne et al. (1994 ▶). For synthesis, see: Antibes et al. (1988 ▶).

Experimental

Crystal data

C₁₇H₂₁BrO
M _r = 321.25
Orthorhombic,
a = 7.3815 (11) Å
b = 13.2067 (19) Å
c = 15.067 (2) Å
V = 1468.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.79 mm⁻¹
T = 123 (2) K
0.30 × 0.26 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.438, T _max = 0.492
12697 measured reflections
2580 independent reflections
2279 reflections with I > 2σ(I)
R _int = 0.049

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.106
S = 0.86
2580 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.59 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1072 Friedel pairs
Flack parameter: 0.340 (15)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808016772/cv2416sup1.cif

e-64-o1212-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016772/cv2416Isup2.hkl

e-64-o1212-Isup2.hkl^{(124.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O1	0.99	2.35	3.003 (5)	123
C17—H17B⋯O1	0.99	2.35	3.004 (4)	123
C4—H4⋯Cgⁱ	0.95	2.66	3.568 (5)	161

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Symmetry code: (i) Inline graphic .

Acknowledgments

The author acknowledges financial support from Zhejiang Police College, China.

supplementary crystallographic information

Comment

The molecule of adamantane has high symmetry, Td, and adamantane crystallizes in the highest space group, Fm3 m (Nordman & Schmitkons, 1965; Amoureux et al., 1980; Amoureux & Bee, 1980). In view of the development of crystal structure systems and the design of organic crystals, it is of interest to study the effects of some simple functional substituents having hydrogen-bonding ability on the symmetry of the crystals of adamantane derivatives. The title compound is an important intermediate of adapalene, which is a new synthetic retinoid of the naphthoic acid series, and was developed for the topical treatment of Acne vulgaris and prevention of some forms of cancer, including the acute promyelocytic leukaemia (Chomienne et al., 1994). Here we report the crystal structure of the title compound (Fig. 1).

In the title compound, the structural parameters of the adamantyl are closely comparable to those found in reported molecule (Pouwer et al., 2007). The C atoms of the adamantine moiety have Csp³ hybridized orbitals, with C—C—C angles in the range 106.6 (4)–111.6 (4)°. The methoxy group and bromo group are coplanar with the benzene ring.

It is of note that the O atoms of the methoxy group participates in formation of two intramolecular C—H···O interactions,and both intramolecular C—H···O interactions are nearly the same (Table.1). Meanwhile, in the crystal structure, an intermolecular C—H···π interaction involving the benzene ring (with the centroid Cg) is observed (Table 1).

Experimental

The title compound was prepared according to the literature method (Antibes et al., 1988). Crystals suitable for X-ray analysis were obtained by slow evaporation of an 2-propanol solution at 295 K.