1-Bromo­adamantane

Abstract

The mol­ecule of the title compound, C₁₀H₁₅Br, shows noncrystallographic mirror symmetry. In the crystal structure, no inter­molecular inter­actions with distances less than the sum of the van der Waals radii of the respective atoms are present.

Related literature

For the crystal structure of the thio­urea solvate of the compound, see Chao et al. (2003 ▶).

Experimental

Crystal data

• C₁₀H₁₅Br

• M _r = 215.13

• Monoclinic,

• a = 10.154 (3) Å

• b = 6.8541 (11) Å

• c = 13.240 (3) Å

• β = 90.027 (17)°

• V = 921.5 (4) ų

• Z = 4

• Mo Kα radiation

• μ = 4.40 mm⁻¹

• T = 200 (2) K

• 0.21 × 0.16 × 0.13 mm

Data collection

• Oxford Xcalibur diffractometer

• Absorption correction: analytical (de Meulenaer & Tompa, 1965 ▶) T _min = 0.462, T _max = 0.614

• 4563 measured reflections

• 1629 independent reflections

• 1313 reflections with I > 2σ(I)

• R _int = 0.054

Refinement

• R[F ² > 2σ(F ²)] = 0.032

• wR(F ²) = 0.080

• S = 1.02

• 1629 reflections

• 101 parameters

• H-atom parameters constrained

• Δρ_max = 0.77 e Å⁻³

• Δρ_min = −0.38 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

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

supplementary crystallographic information

Comment

The structure of the title compound was elucidated for comparison of the influence of different substituents on the geometry of the adamantane framework.

In the molecule the Br atom is bonded to one of the bridgehead positions of the carbocycle (Fig. 1). Bond lengths are normal.

In the crystal structure, only dispersive interactions are present. No intermolecular contacts whose range falls below the sum of the van der Waals radii of the respective atoms are existent.

A similar structure, the thiourea solvate of the compound, has been described by Chao et al. (2003) but showed disorder among the 1-bromoadamantane moiety. However, a comparison of both molecules shows good agreement in terms of bond lengths and angles.

The packing of the compound is shown in Fig. 2.

Experimental

The compound was obtained commercially (ACROS). Crystals suitable for X-ray analysis were obtained upon free evaporation of a solution of the compound in diethyl ether.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.99 Å for methylene groups and C—H 1.00 Å for bridgehead positions) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U_eq(C).

The crystal measured is refined as a twin with a twin-plane perpendicular to [001] (Ebenenzwilling). The volume-to-volume-ratio for the two individuals is found at approximately 1:1 with a batch-scale factor of approximately 0.46.

Figures

Fig. 1.

The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.

Fig. 2.

The packing of the title compound, viewed along [010].

Crystal data

C10H15Br	F(000) = 440
Mr = 215.13	Dx = 1.551 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2345 reflections
a = 10.154 (3) Å	θ = 3.9–26.3°
b = 6.8541 (11) Å	µ = 4.39 mm−1
c = 13.240 (3) Å	T = 200 K
β = 90.027 (17)°	Block, colourless
V = 921.5 (4) Å3	0.21 × 0.16 × 0.13 mm
Z = 4

Data collection

Oxford Xcalibur diffractometer	1629 independent reflections
Radiation source: fine-focus sealed tube	1313 reflections with I > 2σ(I)
graphite	Rint = 0.054
ω scans	θmax = 25.3°, θmin = 3.9°
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	h = −12→11
Tmin = 0.462, Tmax = 0.614	k = −8→8
4563 measured reflections	l = −15→14

Refinement

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0393P)2] where P = (Fo2 + 2Fc2)/3
1629 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.77 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.23244 (6)	0.64478 (6)	0.19046 (4)	0.04391 (18)
C1	0.2412 (4)	0.4548 (6)	0.3057 (3)	0.0281 (9)
C2	0.3872 (4)	0.4075 (6)	0.3225 (4)	0.0361 (11)
H21	0.4369	0.5279	0.3386	0.043*
H22	0.4255	0.3481	0.2610	0.043*
C3	0.1789 (4)	0.5508 (7)	0.3973 (3)	0.0315 (11)
H31	0.0859	0.5840	0.3829	0.038*
H32	0.2266	0.6724	0.4144	0.038*
C4	0.1651 (5)	0.2707 (7)	0.2754 (3)	0.0330 (11)
H41	0.2042	0.2120	0.2140	0.040*
H42	0.0719	0.3031	0.2612	0.040*
C5	0.1743 (6)	0.1266 (7)	0.3651 (4)	0.0356 (14)
H5	0.1251	0.0048	0.3477	0.043*
C6	0.3174 (6)	0.0759 (8)	0.3849 (5)	0.0418 (15)
H61	0.3563	0.0147	0.3241	0.050*
H62	0.3233	−0.0185	0.4413	0.050*
C7	0.3940 (4)	0.2628 (8)	0.4118 (4)	0.0372 (13)
H7	0.4880	0.2294	0.4261	0.045*
C8	0.3321 (6)	0.3549 (7)	0.5051 (4)	0.0345 (14)
H81	0.3807	0.4752	0.5229	0.041*
H82	0.3390	0.2633	0.5627	0.041*
C9	0.1869 (6)	0.4047 (7)	0.4865 (4)	0.0317 (13)
H9	0.1480	0.4648	0.5486	0.038*
C10	0.1118 (5)	0.2199 (8)	0.4592 (4)	0.0369 (13)
H101	0.0184	0.2519	0.4454	0.044*
H102	0.1149	0.1268	0.5163	0.044*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Br1	0.0506 (3)	0.0472 (3)	0.0339 (2)	−0.0028 (3)	−0.0007 (3)	0.0092 (2)
C1	0.030 (2)	0.0264 (19)	0.0282 (19)	−0.0018 (18)	0.003 (4)	0.0013 (18)
C2	0.027 (2)	0.040 (3)	0.042 (3)	−0.006 (2)	0.007 (2)	−0.002 (2)
C3	0.031 (3)	0.026 (2)	0.037 (3)	0.000 (2)	0.001 (2)	−0.005 (2)
C4	0.029 (2)	0.037 (3)	0.033 (2)	−0.008 (2)	−0.001 (2)	−0.009 (2)
C5	0.042 (3)	0.023 (3)	0.042 (3)	−0.010 (2)	0.000 (3)	−0.003 (2)
C6	0.050 (4)	0.029 (3)	0.046 (3)	0.001 (3)	0.006 (3)	−0.002 (3)
C7	0.024 (2)	0.040 (3)	0.048 (4)	−0.006 (3)	−0.005 (2)	0.002 (3)
C8	0.035 (3)	0.036 (3)	0.033 (3)	−0.012 (3)	−0.009 (2)	0.002 (2)
C9	0.036 (3)	0.031 (3)	0.029 (3)	−0.007 (2)	0.003 (2)	−0.003 (2)
C10	0.033 (3)	0.035 (3)	0.043 (3)	−0.008 (2)	0.004 (3)	0.001 (2)

Geometric parameters (Å, °)

Br1—C1	2.008 (4)	C5—C10	1.538 (8)
C1—C3	1.518 (6)	C5—H5	1.0000
C1—C4	1.533 (6)	C6—C7	1.540 (8)
C1—C2	1.533 (6)	C6—H61	0.9900
C2—C7	1.545 (7)	C6—H62	0.9900
C2—H21	0.9900	C7—C8	1.523 (8)
C2—H22	0.9900	C7—H7	1.0000
C3—C9	1.551 (6)	C8—C9	1.533 (7)
C3—H31	0.9900	C8—H81	0.9900
C3—H32	0.9900	C8—H82	0.9900
C4—C5	1.547 (7)	C9—C10	1.522 (7)
C4—H41	0.9900	C9—H9	1.0000
C4—H42	0.9900	C10—H101	0.9900
C5—C6	1.517 (8)	C10—H102	0.9900
C3—C1—C4	110.8 (4)	C5—C6—C7	109.4 (5)
C3—C1—C2	112.3 (4)	C5—C6—H61	109.8
C4—C1—C2	110.6 (4)	C7—C6—H61	109.8
C3—C1—Br1	107.9 (3)	C5—C6—H62	109.8
C4—C1—Br1	108.2 (3)	C7—C6—H62	109.8
C2—C1—Br1	106.9 (3)	H61—C6—H62	108.2
C1—C2—C7	106.8 (4)	C8—C7—C6	108.9 (4)
C1—C2—H21	110.4	C8—C7—C2	109.6 (4)
C7—C2—H21	110.4	C6—C7—C2	109.6 (4)
C1—C2—H22	110.4	C8—C7—H7	109.6
C7—C2—H22	110.4	C6—C7—H7	109.6
H21—C2—H22	108.6	C2—C7—H7	109.6
C1—C3—C9	107.9 (4)	C7—C8—C9	111.1 (5)
C1—C3—H31	110.1	C7—C8—H81	109.4
C9—C3—H31	110.1	C9—C8—H81	109.4
C1—C3—H32	110.1	C7—C8—H82	109.4
C9—C3—H32	110.1	C9—C8—H82	109.4
H31—C3—H32	108.4	H81—C8—H82	108.0
C1—C4—C5	107.1 (4)	C10—C9—C8	109.5 (5)
C1—C4—H41	110.3	C10—C9—C3	109.3 (4)
C5—C4—H41	110.3	C8—C9—C3	108.4 (4)
C1—C4—H42	110.3	C10—C9—H9	109.9
C5—C4—H42	110.3	C8—C9—H9	109.9
H41—C4—H42	108.5	C3—C9—H9	109.9
C6—C5—C10	110.5 (5)	C9—C10—C5	109.4 (4)
C6—C5—C4	109.7 (5)	C9—C10—H101	109.8
C10—C5—C4	109.4 (4)	C5—C10—H101	109.8
C6—C5—H5	109.1	C9—C10—H102	109.8
C10—C5—H5	109.1	C5—C10—H102	109.8
C4—C5—H5	109.1	H101—C10—H102	108.2
C3—C1—C2—C7	61.4 (5)	C5—C6—C7—C2	−60.8 (6)
C4—C1—C2—C7	−62.9 (5)	C1—C2—C7—C8	−58.8 (5)
Br1—C1—C2—C7	179.5 (3)	C1—C2—C7—C6	60.6 (5)
C4—C1—C3—C9	62.2 (5)	C6—C7—C8—C9	−59.1 (6)
C2—C1—C3—C9	−62.0 (5)	C2—C7—C8—C9	60.7 (5)
Br1—C1—C3—C9	−179.5 (3)	C7—C8—C9—C10	59.1 (5)
C3—C1—C4—C5	−62.2 (5)	C7—C8—C9—C3	−60.0 (5)
C2—C1—C4—C5	62.9 (5)	C1—C3—C9—C10	−60.4 (5)
Br1—C1—C4—C5	179.6 (3)	C1—C3—C9—C8	58.9 (5)
C1—C4—C5—C6	−60.9 (6)	C8—C9—C10—C5	−58.0 (6)
C1—C4—C5—C10	60.5 (5)	C3—C9—C10—C5	60.6 (5)
C10—C5—C6—C7	−60.0 (6)	C6—C5—C10—C9	59.7 (6)
C4—C5—C6—C7	60.7 (6)	C4—C5—C10—C9	−61.2 (5)
C5—C6—C7—C8	59.1 (6)