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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o101.
Published online 2008 December 13. doi:  10.1107/S1600536808038452
PMCID: PMC2968026

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 [triangle]).

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Object name is e-65-0o101-scheme1.jpg

Experimental

Crystal data

  • C10H15Br
  • M r = 215.13
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o101-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.77 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

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

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

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

Acknowledgments

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

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 1.2Ueq(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

C10H15BrF(000) = 440
Mr = 215.13Dx = 1.551 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2345 reflections
a = 10.154 (3) Åθ = 3.9–26.3°
b = 6.8541 (11) ŵ = 4.39 mm1
c = 13.240 (3) ÅT = 200 K
β = 90.027 (17)°Block, colourless
V = 921.5 (4) Å30.21 × 0.16 × 0.13 mm
Z = 4

Data collection

Oxford Xcalibur diffractometer1629 independent reflections
Radiation source: fine-focus sealed tube1313 reflections with I > 2σ(I)
graphiteRint = 0.054
ω scansθmax = 25.3°, θmin = 3.9°
Absorption correction: analytical (de Meulenaer & Tompa, 1965)h = −12→11
Tmin = 0.462, Tmax = 0.614k = −8→8
4563 measured reflectionsl = −15→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0393P)2] where P = (Fo2 + 2Fc2)/3
1629 reflections(Δ/σ)max < 0.001
101 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = −0.37 e Å3

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

xyzUiso*/Ueq
Br10.23244 (6)0.64478 (6)0.19046 (4)0.04391 (18)
C10.2412 (4)0.4548 (6)0.3057 (3)0.0281 (9)
C20.3872 (4)0.4075 (6)0.3225 (4)0.0361 (11)
H210.43690.52790.33860.043*
H220.42550.34810.26100.043*
C30.1789 (4)0.5508 (7)0.3973 (3)0.0315 (11)
H310.08590.58400.38290.038*
H320.22660.67240.41440.038*
C40.1651 (5)0.2707 (7)0.2754 (3)0.0330 (11)
H410.20420.21200.21400.040*
H420.07190.30310.26120.040*
C50.1743 (6)0.1266 (7)0.3651 (4)0.0356 (14)
H50.12510.00480.34770.043*
C60.3174 (6)0.0759 (8)0.3849 (5)0.0418 (15)
H610.35630.01470.32410.050*
H620.3233−0.01850.44130.050*
C70.3940 (4)0.2628 (8)0.4118 (4)0.0372 (13)
H70.48800.22940.42610.045*
C80.3321 (6)0.3549 (7)0.5051 (4)0.0345 (14)
H810.38070.47520.52290.041*
H820.33900.26330.56270.041*
C90.1869 (6)0.4047 (7)0.4865 (4)0.0317 (13)
H90.14800.46480.54860.038*
C100.1118 (5)0.2199 (8)0.4592 (4)0.0369 (13)
H1010.01840.25190.44540.044*
H1020.11490.12680.51630.044*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0506 (3)0.0472 (3)0.0339 (2)−0.0028 (3)−0.0007 (3)0.0092 (2)
C10.030 (2)0.0264 (19)0.0282 (19)−0.0018 (18)0.003 (4)0.0013 (18)
C20.027 (2)0.040 (3)0.042 (3)−0.006 (2)0.007 (2)−0.002 (2)
C30.031 (3)0.026 (2)0.037 (3)0.000 (2)0.001 (2)−0.005 (2)
C40.029 (2)0.037 (3)0.033 (2)−0.008 (2)−0.001 (2)−0.009 (2)
C50.042 (3)0.023 (3)0.042 (3)−0.010 (2)0.000 (3)−0.003 (2)
C60.050 (4)0.029 (3)0.046 (3)0.001 (3)0.006 (3)−0.002 (3)
C70.024 (2)0.040 (3)0.048 (4)−0.006 (3)−0.005 (2)0.002 (3)
C80.035 (3)0.036 (3)0.033 (3)−0.012 (3)−0.009 (2)0.002 (2)
C90.036 (3)0.031 (3)0.029 (3)−0.007 (2)0.003 (2)−0.003 (2)
C100.033 (3)0.035 (3)0.043 (3)−0.008 (2)0.004 (3)0.001 (2)

Geometric parameters (Å, °)

Br1—C12.008 (4)C5—C101.538 (8)
C1—C31.518 (6)C5—H51.0000
C1—C41.533 (6)C6—C71.540 (8)
C1—C21.533 (6)C6—H610.9900
C2—C71.545 (7)C6—H620.9900
C2—H210.9900C7—C81.523 (8)
C2—H220.9900C7—H71.0000
C3—C91.551 (6)C8—C91.533 (7)
C3—H310.9900C8—H810.9900
C3—H320.9900C8—H820.9900
C4—C51.547 (7)C9—C101.522 (7)
C4—H410.9900C9—H91.0000
C4—H420.9900C10—H1010.9900
C5—C61.517 (8)C10—H1020.9900
C3—C1—C4110.8 (4)C5—C6—C7109.4 (5)
C3—C1—C2112.3 (4)C5—C6—H61109.8
C4—C1—C2110.6 (4)C7—C6—H61109.8
C3—C1—Br1107.9 (3)C5—C6—H62109.8
C4—C1—Br1108.2 (3)C7—C6—H62109.8
C2—C1—Br1106.9 (3)H61—C6—H62108.2
C1—C2—C7106.8 (4)C8—C7—C6108.9 (4)
C1—C2—H21110.4C8—C7—C2109.6 (4)
C7—C2—H21110.4C6—C7—C2109.6 (4)
C1—C2—H22110.4C8—C7—H7109.6
C7—C2—H22110.4C6—C7—H7109.6
H21—C2—H22108.6C2—C7—H7109.6
C1—C3—C9107.9 (4)C7—C8—C9111.1 (5)
C1—C3—H31110.1C7—C8—H81109.4
C9—C3—H31110.1C9—C8—H81109.4
C1—C3—H32110.1C7—C8—H82109.4
C9—C3—H32110.1C9—C8—H82109.4
H31—C3—H32108.4H81—C8—H82108.0
C1—C4—C5107.1 (4)C10—C9—C8109.5 (5)
C1—C4—H41110.3C10—C9—C3109.3 (4)
C5—C4—H41110.3C8—C9—C3108.4 (4)
C1—C4—H42110.3C10—C9—H9109.9
C5—C4—H42110.3C8—C9—H9109.9
H41—C4—H42108.5C3—C9—H9109.9
C6—C5—C10110.5 (5)C9—C10—C5109.4 (4)
C6—C5—C4109.7 (5)C9—C10—H101109.8
C10—C5—C4109.4 (4)C5—C10—H101109.8
C6—C5—H5109.1C9—C10—H102109.8
C10—C5—H5109.1C5—C10—H102109.8
C4—C5—H5109.1H101—C10—H102108.2
C3—C1—C2—C761.4 (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—C7179.5 (3)C1—C2—C7—C660.6 (5)
C4—C1—C3—C962.2 (5)C6—C7—C8—C9−59.1 (6)
C2—C1—C3—C9−62.0 (5)C2—C7—C8—C960.7 (5)
Br1—C1—C3—C9−179.5 (3)C7—C8—C9—C1059.1 (5)
C3—C1—C4—C5−62.2 (5)C7—C8—C9—C3−60.0 (5)
C2—C1—C4—C562.9 (5)C1—C3—C9—C10−60.4 (5)
Br1—C1—C4—C5179.6 (3)C1—C3—C9—C858.9 (5)
C1—C4—C5—C6−60.9 (6)C8—C9—C10—C5−58.0 (6)
C1—C4—C5—C1060.5 (5)C3—C9—C10—C560.6 (5)
C10—C5—C6—C7−60.0 (6)C6—C5—C10—C959.7 (6)
C4—C5—C6—C760.7 (6)C4—C5—C10—C9−61.2 (5)
C5—C6—C7—C859.1 (6)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2442).

References

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography