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

Cheng, X.-W.

doi:10.1107/S1600536808016772

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1212

doi:10.1107/S1600536808016772

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

Xiang-Wei Cheng ^a ^*

^aZhejiang Police College Experience Center, Zhejiang Police College, Hangzhou 310053, People's Republic of China
^*Correspondence e-mail: zpccxw@126.com

(Received 26 May 2008; accepted 2 June 2008; online 7 June 2008)

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, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.040
wR(F²) = 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)

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
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

2-(1-adamantyl)-4-bromomethoxybenzene top

Crystal data top

C₁₇H₂₁BrO	F(000) = 664
M_r = 321.25	D_x = 1.453 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2580 reflections
a = 7.3815 (11) Å	θ = 2–25.0°
b = 13.2067 (19) Å	µ = 2.79 mm⁻¹
c = 15.067 (2) Å	T = 123 K
V = 1468.8 (4) Å³	Block, colourless
Z = 4	0.30 × 0.26 × 0.25 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2580 independent reflections
Radiation source: fine-focus sealed tube	2279 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
T_min = 0.438, T_max = 0.492	k = −15→14
12697 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0694P)² + 1.9231P] where P = (F_o² + 2F_c²)/3
S = 0.86	(Δ/σ)_max < 0.001
2580 reflections	Δρ_max = 0.51 e Å⁻³
172 parameters	Δρ_min = −0.59 e Å⁻³
0 restraints	Absolute structure: Flack (1983), with 1072 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.340 (15)

Crystal data top

C₁₇H₂₁BrO	V = 1468.8 (4) Å³
M_r = 321.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3815 (11) Å	µ = 2.79 mm⁻¹
b = 13.2067 (19) Å	T = 123 K
c = 15.067 (2) Å	0.30 × 0.26 × 0.25 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2580 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	2279 reflections with I > 2σ(I)
T_min = 0.438, T_max = 0.492	R_int = 0.049
12697 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.106	Δρ_max = 0.51 e Å⁻³
S = 0.86	Δρ_min = −0.59 e Å⁻³
2580 reflections	Absolute structure: Flack (1983), with 1072 Friedel pairs
172 parameters	Absolute structure parameter: 0.340 (15)
0 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.49661 (7)	0.52137 (3)	0.02595 (3)	0.05940 (19)
O1	0.3914 (4)	0.9390 (2)	0.17914 (19)	0.0495 (7)
C8	0.1674 (5)	0.7808 (3)	0.2493 (2)	0.0306 (8)
C17	0.2606 (5)	0.8175 (3)	0.3350 (2)	0.0334 (8)
H17A	0.3496	0.7662	0.3548	0.040*
H17B	0.3269	0.8812	0.3228	0.040*
C2	0.4172 (5)	0.8448 (3)	0.1434 (2)	0.0363 (9)
C11	−0.2109 (5)	0.7762 (4)	0.3180 (3)	0.0512 (11)
H11A	−0.2768	0.7516	0.2650	0.061*
H11B	−0.2999	0.7871	0.3662	0.061*
C12	−0.0155 (7)	0.9143 (3)	0.3787 (3)	0.0495 (10)
H12A	0.0472	0.9785	0.3646	0.059*
H12B	−0.1034	0.9275	0.4270	0.059*
C9	0.0205 (6)	0.8587 (3)	0.2208 (2)	0.0403 (9)
H9A	0.0790	0.9237	0.2052	0.048*
H9B	−0.0441	0.8333	0.1677	0.048*
C7	0.3094 (5)	0.7656 (3)	0.1763 (2)	0.0307 (8)
C14	0.0274 (6)	0.7365 (3)	0.4301 (2)	0.0439 (10)
H14A	−0.0610	0.7469	0.4786	0.053*
H14B	0.1175	0.6858	0.4499	0.053*
C16	0.0668 (5)	0.6818 (3)	0.2726 (3)	0.0374 (9)
H16A	0.0037	0.6562	0.2191	0.045*
H16B	0.1559	0.6300	0.2913	0.045*
C6	0.3380 (5)	0.6697 (3)	0.1394 (2)	0.0346 (8)
H6	0.2673	0.6141	0.1594	0.042*
C4	0.5731 (6)	0.7319 (4)	0.0433 (3)	0.0469 (10)
H4	0.6633	0.7200	−0.0005	0.056*
C1	0.4924 (7)	1.0210 (3)	0.1470 (3)	0.0544 (10)
H1A	0.4601	1.0823	0.1800	0.082*
H1B	0.4660	1.0309	0.0839	0.082*
H1C	0.6219	1.0070	0.1547	0.082*
C3	0.5459 (6)	0.8275 (3)	0.0770 (3)	0.0472 (11)
H3	0.6155	0.8825	0.0549	0.057*
C15	−0.0708 (5)	0.6981 (3)	0.3467 (3)	0.0428 (9)
H15	−0.1328	0.6326	0.3604	0.051*
C13	0.1216 (5)	0.8356 (3)	0.4087 (2)	0.0380 (9)
H13	0.1854	0.8607	0.4629	0.046*
C10	−0.1150 (6)	0.8754 (4)	0.2966 (3)	0.0472 (11)
H10	−0.2068	0.9267	0.2777	0.057*
C5	0.4671 (5)	0.6541 (3)	0.0743 (2)	0.0400 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0757 (3)	0.0442 (3)	0.0583 (3)	0.0164 (3)	0.0146 (3)	−0.00538 (19)
O1	0.0647 (19)	0.0356 (16)	0.0483 (16)	−0.0131 (14)	0.0155 (15)	−0.0039 (14)
C8	0.0306 (19)	0.030 (2)	0.0313 (19)	0.0015 (15)	0.0001 (14)	0.0022 (15)
C17	0.0330 (18)	0.038 (2)	0.0294 (18)	−0.0019 (16)	−0.0002 (15)	0.0021 (16)
C2	0.041 (2)	0.037 (2)	0.0314 (18)	−0.0044 (18)	0.0016 (16)	0.0021 (16)
C11	0.029 (2)	0.071 (3)	0.053 (3)	0.001 (2)	0.0018 (19)	0.000 (2)
C12	0.056 (2)	0.050 (3)	0.043 (2)	0.014 (2)	0.009 (2)	−0.0064 (17)
C9	0.040 (2)	0.045 (2)	0.0352 (17)	0.006 (2)	−0.0033 (17)	0.0085 (15)
C7	0.0307 (17)	0.034 (2)	0.0274 (17)	−0.0012 (15)	−0.0032 (14)	0.0003 (15)
C14	0.040 (2)	0.057 (3)	0.0337 (18)	0.005 (2)	0.0062 (17)	0.0110 (17)
C16	0.036 (2)	0.034 (2)	0.043 (2)	−0.0045 (16)	0.0017 (15)	0.0047 (18)
C6	0.035 (2)	0.037 (2)	0.0327 (18)	−0.0003 (16)	0.0008 (14)	0.0045 (16)
C4	0.045 (2)	0.057 (3)	0.039 (2)	−0.002 (2)	0.0116 (17)	−0.0006 (19)
C1	0.056 (2)	0.040 (2)	0.068 (3)	−0.010 (3)	0.000 (2)	0.0100 (19)
C3	0.050 (3)	0.051 (3)	0.040 (2)	−0.013 (2)	0.0087 (18)	0.0027 (19)
C15	0.037 (2)	0.046 (2)	0.046 (2)	−0.0059 (17)	0.0053 (17)	0.0051 (19)
C13	0.040 (2)	0.046 (2)	0.0274 (18)	0.0017 (17)	0.0017 (16)	−0.0017 (17)
C10	0.036 (2)	0.060 (3)	0.046 (2)	0.018 (2)	−0.0030 (18)	0.007 (2)
C5	0.045 (2)	0.040 (2)	0.0353 (18)	0.0066 (18)	0.0013 (17)	−0.0023 (16)

Geometric parameters (Å, º) top

Br1—C5	1.911 (4)	C9—H9B	0.9900
O1—C2	1.369 (5)	C7—C6	1.399 (5)
O1—C1	1.400 (5)	C14—C13	1.516 (6)
C8—C7	1.533 (5)	C14—C15	1.536 (6)
C8—C17	1.541 (5)	C14—H14A	0.9900
C8—C16	1.544 (5)	C14—H14B	0.9900
C8—C9	1.555 (5)	C16—C15	1.525 (6)
C17—C13	1.531 (5)	C16—H16A	0.9900
C17—H17A	0.9900	C16—H16B	0.9900
C17—H17B	0.9900	C6—C5	1.383 (5)
C2—C3	1.398 (5)	C6—H6	0.9500
C2—C7	1.405 (5)	C4—C5	1.373 (6)
C11—C10	1.523 (7)	C4—C3	1.375 (6)
C11—C15	1.524 (6)	C4—H4	0.9500
C11—H11A	0.9900	C1—H1A	0.9800
C11—H11B	0.9900	C1—H1B	0.9800
C12—C13	1.519 (6)	C1—H1C	0.9800
C12—C10	1.528 (6)	C3—H3	0.9500
C12—H12A	0.9900	C15—H15	1.0000
C12—H12B	0.9900	C13—H13	1.0000
C9—C10	1.535 (6)	C10—H10	1.0000
C9—H9A	0.9900

C2—O1—C1	119.5 (3)	C15—C16—C8	111.5 (3)
C7—C8—C17	109.7 (3)	C15—C16—H16A	109.3
C7—C8—C16	112.4 (3)	C8—C16—H16A	109.3
C17—C8—C16	106.9 (3)	C15—C16—H16B	109.3
C7—C8—C9	111.4 (3)	C8—C16—H16B	109.3
C17—C8—C9	109.6 (3)	H16A—C16—H16B	108.0
C16—C8—C9	106.7 (3)	C5—C6—C7	121.4 (4)
C13—C17—C8	110.9 (3)	C5—C6—H6	119.3
C13—C17—H17A	109.4	C7—C6—H6	119.3
C8—C17—H17A	109.4	C5—C4—C3	118.5 (4)
C13—C17—H17B	109.4	C5—C4—H4	120.7
C8—C17—H17B	109.4	C3—C4—H4	120.7
H17A—C17—H17B	108.0	O1—C1—H1A	109.5
O1—C2—C3	121.6 (4)	O1—C1—H1B	109.5
O1—C2—C7	117.4 (3)	H1A—C1—H1B	109.5
C3—C2—C7	121.0 (4)	O1—C1—H1C	109.5
C10—C11—C15	109.1 (3)	H1A—C1—H1C	109.5
C10—C11—H11A	109.9	H1B—C1—H1C	109.5
C15—C11—H11A	109.9	C4—C3—C2	120.9 (4)
C10—C11—H11B	109.9	C4—C3—H3	119.6
C15—C11—H11B	109.9	C2—C3—H3	119.6
H11A—C11—H11B	108.3	C11—C15—C16	109.9 (3)
C13—C12—C10	109.3 (3)	C11—C15—C14	109.2 (4)
C13—C12—H12A	109.8	C16—C15—C14	109.4 (3)
C10—C12—H12A	109.8	C11—C15—H15	109.5
C13—C12—H12B	109.8	C16—C15—H15	109.5
C10—C12—H12B	109.8	C14—C15—H15	109.5
H12A—C12—H12B	108.3	C14—C13—C12	110.3 (3)
C10—C9—C8	110.1 (3)	C14—C13—C17	109.1 (3)
C10—C9—H9A	109.6	C12—C13—C17	109.7 (3)
C8—C9—H9A	109.6	C14—C13—H13	109.2
C10—C9—H9B	109.6	C12—C13—H13	109.2
C8—C9—H9B	109.6	C17—C13—H13	109.2
H9A—C9—H9B	108.2	C11—C10—C12	109.9 (4)
C6—C7—C2	116.7 (3)	C11—C10—C9	109.7 (4)
C6—C7—C8	120.5 (3)	C12—C10—C9	109.7 (3)
C2—C7—C8	122.8 (3)	C11—C10—H10	109.1
C13—C14—C15	109.1 (3)	C12—C10—H10	109.1
C13—C14—H14A	109.9	C9—C10—H10	109.1
C15—C14—H14A	109.9	C4—C5—C6	121.5 (4)
C13—C14—H14B	109.9	C4—C5—Br1	119.5 (3)
C15—C14—H14B	109.9	C6—C5—Br1	119.0 (3)
H14A—C14—H14B	108.3

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁BrO
M_r	321.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	123
a, b, c (Å)	7.3815 (11), 13.2067 (19), 15.067 (2)
V (Å³)	1468.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.79
Crystal size (mm)	0.30 × 0.26 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.438, 0.492
No. of measured, independent and observed [I > 2σ(I)] reflections	12697, 2580, 2279
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 0.86
No. of reflections	2580
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.59
Absolute structure	Flack (1983), with 1072 Friedel pairs
Absolute structure parameter	0.340 (15)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x−1/2, −y+1/2, −z+1.

Acknowledgements

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

References

Amoureux, J. P. & Bee, M. (1980). Acta Cryst. B36, 2636–2642. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Amoureux, J. P., Bee, M. & Damien, J. C. (1980). Acta Cryst. B36, 2633–2636. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Antibes, B. S., Grasse, J. E. & Nice, J. B. (1988). US Patent 4 717 720. Google Scholar
Bruker (2002). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chomienne, C., Ballerini, P., Balitrand, N., Amor, M., Bernard, J. F., Boivin, P., Daniel, M. T., Berger, R., Castaigne, S. & Degos, L. (1994). Lancet ii, 344, 746–747. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Nordman, C. E. & Schmitkons, D. L. (1965). Acta Cryst. 18, 764–767. CSD CrossRef IUCr Journals Web of Science Google Scholar
Pouwer, R. H., Harper, J. B., Vyakaranam, K., Michl, J., Williams, C. M., Jessen, C. H. & Bernhardt, P. V. (2007). Eur. J. Org. Chem. pp. 241–248. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar