1-(Bromo-meth-yl)adamantane.

The title compound, C(11)H(17)Br, has crystallographically imposed mirror symmetry in the solid state with mol-ecules bis-ected by mirror planes parallel to the crystallographic ac plane (five C atoms, three H atoms and the Br atom lie on the mirror plane). The asymmetric unit contains one half-mol-ecule. The crystal packing is stabilized only via weak non-specific van der Waals inter-actions.

Related literature

For the synthetic procedure, see: Nordlander et al. (1966 ▶). For the structure of a related non-polar adamantane derivate, see: Rouchal et al. (2010 ▶).

Experimental

Crystal data

C11H17Br

M = 229.16

Monoclinic,

a = 10.7250 (3) Å

b = 7.0066 (3) Å

c = 13.4479 (4) Å

β = 101.801 (3)°

V = 989.19 (6) Å3

Z = 4

Mo Kα radiation

μ = 4.10 mm−1

T = 120 K

0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.480, T max = 1.000

5102 measured reflections

951 independent reflections

900 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.048

S = 1.08

951 reflections

64 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023695/jh2298sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023695/jh2298Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023695/jh2298Isup3.cml

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

C11H17Br	F(000) = 472
Mr = 229.16	Dx = 1.539 Mg m−3
Monoclinic, C2/m	Melting point: 315 K
Hall symbol: -C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 10.7250 (3) Å	Cell parameters from 4311 reflections
b = 7.0066 (3) Å	θ = 3.1–27.2°
c = 13.4479 (4) Å	µ = 4.10 mm−1
β = 101.801 (3)°	T = 120 K
V = 989.19 (6) Å3	Block, colourless
Z = 4	0.40 × 0.40 × 0.30 mm

Oxford Diffraction Xcalibur Sapphire2 diffractometer	951 independent reflections
Radiation source: Enhance (Mo) X-ray Source	900 reflections with I > 2σ(I)
graphite	Rint = 0.014
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −8→4
Tmin = 0.480, Tmax = 1.000	l = −15→15
5102 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.017	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.029P)2 + 0.8238P] where P = (Fo2 + 2Fc2)/3
951 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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 > 2σ(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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.35255 (2)	0.0000	0.046661 (18)	0.02707 (11)
C1	0.1776 (2)	0.0000	0.18798 (16)	0.0146 (5)
C2	0.0362 (2)	0.0000	0.19634 (17)	0.0175 (5)
H2A	−0.0068	0.1144	0.1621	0.021*	0.50
H2B	−0.0068	−0.1144	0.1621	0.021*	0.50
C3	0.0259 (2)	0.0000	0.30840 (17)	0.0188 (5)
H3	−0.0660	0.0000	0.3130	0.023*
C4	0.09066 (14)	0.1784 (3)	0.36097 (12)	0.0199 (4)
H4A	0.0834	0.1794	0.4332	0.024*
H4B	0.0483	0.2943	0.3279	0.024*
C5	0.23165 (14)	0.1783 (3)	0.35368 (12)	0.0169 (4)
H5	0.2742	0.2948	0.3878	0.020*
C6	0.24109 (14)	0.1789 (2)	0.24137 (12)	0.0163 (3)
H6A	0.1988	0.2942	0.2077	0.020*
H6B	0.3318	0.1824	0.2360	0.020*
C7	0.2966 (2)	0.0000	0.40589 (17)	0.0183 (5)
H7A	0.3878	0.0000	0.4021	0.022*
H7B	0.2908	0.0000	0.4784	0.022*
C8	0.1790 (2)	0.0000	0.07521 (18)	0.0202 (5)
H8A	0.1329	0.1141	0.0435	0.024*	0.50
H8B	0.1329	−0.1141	0.0435	0.024*	0.50

	U11	U22	U33	U12	U13	U23
Br1	0.03772 (17)	0.02270 (17)	0.02531 (16)	0.000	0.01703 (11)	0.000
C1	0.0154 (10)	0.0148 (12)	0.0125 (11)	0.000	0.0004 (8)	0.000
C2	0.0128 (10)	0.0162 (12)	0.0204 (12)	0.000	−0.0037 (9)	0.000
C3	0.0106 (10)	0.0236 (13)	0.0214 (12)	0.000	0.0015 (9)	0.000
C4	0.0163 (7)	0.0228 (10)	0.0203 (8)	0.0031 (7)	0.0034 (6)	−0.0032 (7)
C5	0.0148 (7)	0.0176 (9)	0.0173 (8)	−0.0026 (7)	0.0010 (6)	−0.0046 (7)
C6	0.0157 (7)	0.0145 (8)	0.0178 (8)	−0.0012 (7)	0.0014 (6)	−0.0001 (7)
C7	0.0132 (10)	0.0273 (14)	0.0135 (11)	0.000	0.0004 (8)	0.000
C8	0.0230 (11)	0.0195 (13)	0.0167 (11)	0.000	0.0010 (9)	0.000

Br1—C8	1.975 (2)	C4—H4A	0.9900
C1—C8	1.520 (3)	C4—H4B	0.9900
C1—C6	1.533 (2)	C5—C7	1.529 (2)
C1—C6i	1.533 (2)	C5—C6	1.534 (2)
C1—C2	1.544 (3)	C5—H5	1.0000
C2—C3	1.533 (3)	C6—H6A	0.9900
C2—H2A	0.9900	C6—H6B	0.9900
C2—H2B	0.9900	C7—C5i	1.529 (2)
C3—C4	1.531 (2)	C7—H7A	0.9900
C3—C4i	1.531 (2)	C7—H7B	0.9900
C3—H3	1.0000	C8—H8A	0.9900
C4—C5	1.535 (2)	C8—H8B	0.9900
C8—C1—C6	111.91 (12)	C7—C5—C6	109.78 (14)
C8—C1—C6i	111.91 (12)	C7—C5—C4	109.45 (14)
C6—C1—C6i	109.67 (17)	C6—C5—C4	109.09 (12)
C8—C1—C2	106.47 (17)	C7—C5—H5	109.5
C6—C1—C2	108.36 (12)	C6—C5—H5	109.5
C6i—C1—C2	108.36 (12)	C4—C5—H5	109.5
C3—C2—C1	109.91 (17)	C1—C6—C5	110.28 (14)
C3—C2—H2A	109.7	C1—C6—H6A	109.6
C1—C2—H2A	109.7	C5—C6—H6A	109.6
C3—C2—H2B	109.7	C1—C6—H6B	109.6
C1—C2—H2B	109.7	C5—C6—H6B	109.6
H2A—C2—H2B	108.2	H6A—C6—H6B	108.1
C4—C3—C4i	109.48 (18)	C5i—C7—C5	109.57 (17)
C4—C3—C2	109.69 (12)	C5i—C7—H7A	109.8
C4i—C3—C2	109.69 (12)	C5—C7—H7A	109.8
C4—C3—H3	109.3	C5i—C7—H7B	109.8
C4i—C3—H3	109.3	C5—C7—H7B	109.8
C2—C3—H3	109.3	H7A—C7—H7B	108.2
C3—C4—C5	109.26 (14)	C1—C8—Br1	113.35 (15)
C3—C4—H4A	109.8	C1—C8—H8A	108.9
C5—C4—H4A	109.8	Br1—C8—H8A	108.9
C3—C4—H4B	109.8	C1—C8—H8B	108.9
C5—C4—H4B	109.8	Br1—C8—H8B	108.9
H4A—C4—H4B	108.3	H8A—C8—H8B	107.7