Acta Cryst. (2009). E65, o101 [ doi:10.1107/S1600536808038452 ]
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.
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.
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.
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).
![[Figure 1]](./hg2442fig1thm.gif)
| 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. |
![[Figure 2]](./hg2442fig2thm.gif)
| Fig. 2. The packing of the title compound, viewed along [010]. |
| 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 |
| 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 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 |
| C10H15Br | V = 921.5 (4) Å3 |
| Mr = 215.13 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 10.154 (3) Å | µ = 4.39 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)° |
| Oxford Xcalibur diffractometer | 1629 independent reflections |
| Absorption correction: analytical (de Meulenaer & Tompa, 1965) | 1313 reflections with I > 2σ(I) |
| Tmin = 0.462, Tmax = 0.614 | Rint = 0.054 |
| 4563 measured reflections | θmax = 25.3° |
| R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
| wR(F2) = 0.080 | Δρmax = 0.77 e Å−3 |
| S = 1.02 | Δρmin = −0.37 e Å−3 |
| 1629 reflections | Absolute structure: ? |
| 101 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
| 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* |
| 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) |
| 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) |
Professor Dr Klapötke is thanked for generous allocation of measurement time on the diffractometer.
Chao, M.-H., Kariuki, B. M., Harris, K. D. M., Collins, S. P. & Laundy, D. (2003). Angew. Chem. Int. Ed. 42, 2982–2985.
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.
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.