1-Bromo­adamantane

Betz, R.; Klüfers, P.; Mayer, P.

doi:10.1107/S1600536808038452

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o101

doi:10.1107/S1600536808038452

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1-Bromoadamantane

Richard Betz,^a Peter Klüfers ^a ^* and Peter Mayer ^a

^aLudwig-Maximilians Universität, Department Chemie und Biochemie, Butenandtstrasse 5–13 (Haus D), 81377 München, Germany
^*Correspondence e-mail: kluef@cup.uni-muenchen.de

(Received 7 November 2008; accepted 18 November 2008; online 13 December 2008)

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, P 2₁ /c
a = 10.154 (3) Å
b = 6.8541 (11) Å
c = 13.240 (3) Å
β = 90.027 (17)°
V = 921.5 (4) Å³
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[F² > 2σ(F²)] = 0.032
wR(F²) = 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 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038452/hg2442sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038452/hg2442Isup2.hkl

checkCIF report

Comment top

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 top

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

Experimental top

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.

Computing details top

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 top

	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 top

Crystal data top

C₁₀H₁₅Br	F(000) = 440
M_r = 215.13	D_x = 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) Å³	0.21 × 0.16 × 0.13 mm
Z = 4

Data collection top

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

Refinement top

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(F_o²) + (0.0393P)²] where P = (F_o² + 2F_c²)/3
1629 reflections	(Δ/σ)_max < 0.001
101 parameters	Δρ_max = 0.77 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₀H₁₅Br	V = 921.5 (4) Å³
M_r = 215.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.154 (3) Å	µ = 4.40 mm⁻¹
b = 6.8541 (11) Å	T = 200 K
c = 13.240 (3) Å	0.21 × 0.16 × 0.13 mm
β = 90.027 (17)°

Data collection top

Oxford Xcalibur diffractometer	1629 independent reflections
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	1313 reflections with I > 2σ(I)
T_min = 0.462, T_max = 0.614	R_int = 0.054
4563 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.02	Δρ_max = 0.77 e Å⁻³
1629 reflections	Δρ_min = −0.38 e Å⁻³
101 parameters

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

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₀H₁₅Br
M_r	215.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	10.154 (3), 6.8541 (11), 13.240 (3)
β (°)	90.027 (17)
V (Å³)	921.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.40
Crystal size (mm)	0.21 × 0.16 × 0.13

Data collection
Diffractometer	Oxford Xcalibur diffractometer
Absorption correction	Analytical (de Meulenaer & Tompa, 1965)
T_min, T_max	0.462, 0.614
No. of measured, independent and observed [I > 2σ(I)] reflections	4563, 1629, 1313
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.080, 1.02
No. of reflections	1629
No. of parameters	101
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.77, −0.38

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Acknowledgements

Professor Dr Klapötke is thanked for generous allocation of measurement time on the diffractometer.

References

Chao, M.-H., Kariuki, B. M., Harris, K. D. M., Collins, S. P. & Laundy, D. (2003). Angew. Chem. Int. Ed. 42, 2982–2985. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Meulenaer, J. de & Tompa, H. (1965). Acta Cryst. 19, 1014–1018. CrossRef IUCr Journals Web of Science Google Scholar
Oxford Diffraction (2005). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar