1-Bromo­adamantane

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.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.032
• wR factor = 0.080
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
            Value of measurement temperature given =   200.000
            Value of melting point given =     0.000
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.04

Author Response: crystal is twinned, twinning was accounted for by TWIN 1 0 0 0 1 0 0 0 -1

PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          7

Author Response: situation checked, no obvious reason for alert

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. 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.

Related literature

The compound was obtained commercially (ACROS). For the crystal structure of the thiourea solvate of the compound, see Chao et al. (2003).

S2. 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.

S3. 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.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); 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 (Sheldrick, 2008).

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].

1-Bromoadamantane

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 = 4.40 mm^−1
c = 13.240 (3) Å	T = 200 K
β = 90.027 (17)°	Block, colourless
V = 921.5 (4) Å^3	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 monochromator	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 F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0393P)^2] where P = (Fo^2 + 2Fc^2)/3
1629 reflections	(Δ/σ)max < 0.001
101 parameters	Δρmax = 0.77 e Å^−3
0 restraints	Δρmin = −0.38 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)

	U^11	U^22	U^33	U^12	U^13	U^23
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, º)

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)