1,3,5,7-Tetra-bromo-adamantane.

In the pyramidal-shaped mol-ecule of the title compound, C(10)H(12)Br(4), the four terminal Br-C bond distances are nearly identical, ranging from 1.964 (4) to 1.974 (4) Å. The Br⋯Br distance of 3.6553 (7) Å indicates van der Waals contacts between mol-ecules in the crystal structure.

Related literature

For applications of adamantane compounds, see: Kim et al. (2001 ▶); Kozhushkov et al. (2005 ▶); Li et al. (2003 ▶). For related structures, see: Pedireddi et al. (1994 ▶); Reddy et al. (1995 ▶). For the synthesis, see: Murray et al. (1989 ▶); Migulin & Menger (2001 ▶).

Experimental

Crystal data

C10H12Br4

M = 451.84

Monoclinic,

a = 11.7669 (4) Å

b = 9.0612 (3) Å

c = 12.1493 (4) Å

β = 98.529 (2)°

V = 1281.06 (7) Å3

Z = 4

Mo Kα radiation

μ = 12.53 mm−1

T = 296 K

0.35 × 0.32 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.097, T max = 0.153

7087 measured reflections

2511 independent reflections

1892 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.077

S = 1.01

2511 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.67 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054474/xu5115sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054474/xu5115Isup2.hkl

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

C10H12Br4	F(000) = 848
Mr = 451.84	Dx = 2.343 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2005 reflections
a = 11.7669 (4) Å	θ = 2.6–25.9°
b = 9.0612 (3) Å	µ = 12.53 mm−1
c = 12.1493 (4) Å	T = 296 K
β = 98.529 (2)°	Block, colourless
V = 1281.06 (7) Å3	0.35 × 0.32 × 0.24 mm
Z = 4

Bruker APEXII CCD diffractometer	2511 independent reflections
Radiation source: fine-focus sealed tube	1892 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −13→14
Tmin = 0.097, Tmax = 0.153	k = −11→9
7087 measured reflections	l = −14→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0333P)2 + 0.419P] where P = (Fo2 + 2Fc2)/3
2511 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.67 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 > 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.

	x	y	z	Uiso*/Ueq
Br1	1.09687 (5)	0.62981 (5)	0.32537 (5)	0.05014 (17)
Br2	1.16582 (4)	0.01485 (5)	0.39605 (5)	0.05204 (18)
Br3	0.71851 (4)	0.26097 (6)	0.35978 (5)	0.05166 (17)
Br4	0.94466 (5)	0.22452 (6)	−0.02140 (4)	0.04818 (16)
C1	1.0321 (4)	0.4324 (5)	0.2896 (4)	0.0313 (10)
C2	1.1152 (4)	0.3177 (5)	0.3482 (4)	0.0366 (11)
H2A	1.1892	0.3251	0.3226	0.044*
H2B	1.1262	0.3336	0.4280	0.044*
C3	1.0625 (3)	0.1664 (4)	0.3203 (4)	0.0311 (10)
C4	0.9471 (4)	0.1532 (5)	0.3643 (4)	0.0365 (11)
H4A	0.9144	0.0558	0.3487	0.044*
H4B	0.9576	0.1691	0.4441	0.044*
C5	0.8681 (4)	0.2707 (5)	0.3050 (4)	0.0335 (10)
C6	0.9174 (4)	0.4244 (5)	0.3321 (4)	0.0352 (11)
H6A	0.8656	0.4991	0.2963	0.042*
H6B	0.9279	0.4411	0.4118	0.042*
C7	0.8488 (3)	0.2456 (5)	0.1789 (4)	0.0341 (11)
H7A	0.8154	0.1490	0.1614	0.041*
H7B	0.7971	0.3198	0.1422	0.041*
C8	0.9661 (4)	0.2567 (4)	0.1403 (4)	0.0312 (10)
C9	1.0165 (4)	0.4106 (5)	0.1642 (4)	0.0329 (10)
H9A	1.0899	0.4188	0.1373	0.039*
H9B	0.9650	0.4848	0.1274	0.039*
C10	1.0470 (4)	0.1384 (4)	0.1955 (4)	0.0351 (11)
H10A	1.1204	0.1438	0.1685	0.042*
H10B	1.0145	0.0411	0.1787	0.042*

	U11	U22	U33	U12	U13	U23
Br1	0.0643 (4)	0.0367 (3)	0.0492 (3)	−0.0179 (2)	0.0078 (3)	−0.0076 (2)
Br2	0.0501 (3)	0.0462 (3)	0.0589 (4)	0.0088 (2)	0.0049 (3)	0.0190 (3)
Br3	0.0371 (3)	0.0639 (3)	0.0582 (4)	−0.0055 (2)	0.0214 (3)	−0.0025 (3)
Br4	0.0573 (3)	0.0577 (3)	0.0292 (3)	−0.0008 (2)	0.0054 (2)	−0.0053 (2)
C1	0.033 (2)	0.026 (2)	0.035 (3)	−0.0085 (18)	0.005 (2)	−0.004 (2)
C2	0.031 (2)	0.046 (3)	0.032 (3)	−0.006 (2)	0.002 (2)	−0.001 (2)
C3	0.030 (2)	0.028 (2)	0.034 (3)	0.0008 (18)	0.002 (2)	0.007 (2)
C4	0.043 (3)	0.039 (3)	0.029 (3)	−0.007 (2)	0.009 (2)	0.003 (2)
C5	0.030 (2)	0.036 (2)	0.036 (3)	−0.0030 (19)	0.012 (2)	−0.002 (2)
C6	0.042 (3)	0.032 (2)	0.032 (3)	0.000 (2)	0.005 (2)	−0.007 (2)
C7	0.029 (2)	0.037 (2)	0.036 (3)	−0.0058 (19)	0.006 (2)	−0.001 (2)
C8	0.038 (2)	0.034 (2)	0.020 (2)	−0.0029 (19)	−0.001 (2)	−0.0001 (19)
C9	0.036 (2)	0.034 (2)	0.028 (2)	−0.0040 (19)	0.005 (2)	0.003 (2)
C10	0.037 (2)	0.031 (2)	0.039 (3)	−0.0036 (19)	0.010 (2)	−0.004 (2)

Br1—C1	1.967 (4)	C4—H4B	0.9700
Br2—C3	1.969 (4)	C5—C6	1.526 (6)
Br3—C5	1.974 (4)	C5—C7	1.532 (6)
Br4—C8	1.964 (4)	C6—H6A	0.9700
C1—C6	1.517 (5)	C6—H6B	0.9700
C1—C9	1.520 (6)	C7—C8	1.525 (6)
C1—C2	1.529 (6)	C7—H7A	0.9700
C2—C3	1.522 (6)	C7—H7B	0.9700
C2—H2A	0.9700	C8—C10	1.522 (6)
C2—H2B	0.9700	C8—C9	1.527 (6)
C3—C10	1.522 (6)	C9—H9A	0.9700
C3—C4	1.537 (6)	C9—H9B	0.9700
C4—C5	1.522 (6)	C10—H10A	0.9700
C4—H4A	0.9700	C10—H10B	0.9700
C6—C1—C9	110.7 (4)	C1—C6—C5	107.4 (3)
C6—C1—C2	110.4 (4)	C1—C6—H6A	110.2
C9—C1—C2	110.6 (3)	C5—C6—H6A	110.2
C6—C1—Br1	107.6 (3)	C1—C6—H6B	110.2
C9—C1—Br1	109.0 (3)	C5—C6—H6B	110.2
C2—C1—Br1	108.4 (3)	H6A—C6—H6B	108.5
C3—C2—C1	107.3 (3)	C8—C7—C5	107.0 (3)
C3—C2—H2A	110.3	C8—C7—H7A	110.3
C1—C2—H2A	110.3	C5—C7—H7A	110.3
C3—C2—H2B	110.3	C8—C7—H7B	110.3
C1—C2—H2B	110.3	C5—C7—H7B	110.3
H2A—C2—H2B	108.5	H7A—C7—H7B	108.6
C2—C3—C10	110.9 (4)	C10—C8—C7	110.7 (3)
C2—C3—C4	110.1 (3)	C10—C8—C9	111.0 (3)
C10—C3—C4	110.6 (4)	C7—C8—C9	110.2 (3)
C2—C3—Br2	108.7 (3)	C10—C8—Br4	108.4 (3)
C10—C3—Br2	108.9 (3)	C7—C8—Br4	108.1 (3)
C4—C3—Br2	107.4 (3)	C9—C8—Br4	108.3 (3)
C5—C4—C3	106.9 (3)	C1—C9—C8	107.2 (3)
C5—C4—H4A	110.3	C1—C9—H9A	110.3
C3—C4—H4A	110.3	C8—C9—H9A	110.3
C5—C4—H4B	110.3	C1—C9—H9B	110.3
C3—C4—H4B	110.3	C8—C9—H9B	110.3
H4A—C4—H4B	108.6	H9A—C9—H9B	108.5
C4—C5—C6	110.5 (4)	C8—C10—C3	107.3 (3)
C4—C5—C7	111.1 (3)	C8—C10—H10A	110.3
C6—C5—C7	110.3 (4)	C3—C10—H10A	110.3
C4—C5—Br3	108.8 (3)	C8—C10—H10B	110.3
C6—C5—Br3	107.3 (3)	C3—C10—H10B	110.3
C7—C5—Br3	108.9 (3)	H10A—C10—H10B	108.5
C6—C1—C2—C3	61.7 (5)	C4—C5—C7—C8	−61.2 (4)
C9—C1—C2—C3	−61.2 (4)	C6—C5—C7—C8	61.6 (4)
Br1—C1—C2—C3	179.3 (3)	Br3—C5—C7—C8	179.0 (3)
C1—C2—C3—C10	61.1 (4)	C5—C7—C8—C10	61.3 (4)
C1—C2—C3—C4	−61.7 (5)	C5—C7—C8—C9	−61.9 (4)
C1—C2—C3—Br2	−179.2 (3)	C5—C7—C8—Br4	179.8 (3)
C2—C3—C4—C5	61.8 (5)	C6—C1—C9—C8	−61.7 (4)
C10—C3—C4—C5	−61.2 (4)	C2—C1—C9—C8	61.1 (4)
Br2—C3—C4—C5	−179.9 (3)	Br1—C1—C9—C8	−179.9 (3)
C3—C4—C5—C6	−61.7 (4)	C10—C8—C9—C1	−61.1 (4)
C3—C4—C5—C7	61.0 (4)	C7—C8—C9—C1	61.9 (4)
C3—C4—C5—Br3	−179.2 (3)	Br4—C8—C9—C1	180.0 (3)
C9—C1—C6—C5	61.4 (5)	C7—C8—C10—C3	−62.0 (4)
C2—C1—C6—C5	−61.4 (5)	C9—C8—C10—C3	60.8 (4)
Br1—C1—C6—C5	−179.6 (3)	Br4—C8—C10—C3	179.7 (3)
C4—C5—C6—C1	61.8 (5)	C2—C3—C10—C8	−60.8 (4)
C7—C5—C6—C1	−61.3 (4)	C4—C3—C10—C8	61.7 (4)
Br3—C5—C6—C1	−179.7 (3)	Br2—C3—C10—C8	179.5 (3)