Acta Cryst. (2007). E63, o3971 [ doi:10.1107/S1600536807042602 ]
In the title compound, C8H8Br2, the bond lengths and angles are in the normal range. All non-H atoms are coplanar.
The title compound was synthesized according to a method described previously (Lawson et al., 1968). The reaction solution was diluted with diethyl ether and washed with brine. The organic solution was dried over MgSO4 and the solvent removed. Recrystallization in MeOH to give product as white crystals. 1H-NMR (300 MHz, CDCl3): (p.p.m.) = 7.35 (s, 2H), 2.17 (s, 6H). Analysis calculated for C8H8Br2: C 36.40, H 3.05; found (%): C 35.92, H 3.38.
The structure was solved by direct methods. All H atoms were placed at geometrically idealized positions and were treated as riding atoms, with C—H = 0.93 Å (aromatic) or 0.96 Å (methyl), and Uiso(H) = 1.2Ueq for aromatic and 1.5Ueq for methyl H atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: XPREP (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
![[Figure 1]](./bx2106fig1thm.gif)
| Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. |
| C8H8Br2 | F000 = 504 |
| Mr = 263.96 | Dx = 1.980 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: -P2yn | Cell parameters from 1764 reflections |
| a = 9.383 (4) Å | θ = 2.4–25.1º |
| b = 7.918 (3) Å | µ = 9.08 mm−1 |
| c = 12.612 (5) Å | T = 298 (2) K |
| β = 109.041 (6)º | Block, white |
| V = 885.7 (6) Å3 | 0.20 × 0.12 × 0.10 mm |
| Z = 4 |
| Bruker SMART CCD diffractometer | 1735 independent reflections |
| Radiation source: fine-focus sealed tube | 1346 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.024 |
| T = 298(2) K | θmax = 26.0º |
| ω scans | θmin = 2.4º |
| Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −8→11 |
| Tmin = 0.264, Tmax = 0.464 | k = −7→9 |
| 4542 measured reflections | l = −15→15 |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0481P)2 + 0.5399P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max = 0.001 |
| 1735 reflections | Δρmax = 0.69 e Å−3 |
| 93 parameters | Δρmin = −0.34 e Å−3 |
| Primary atom site location: structure-invariant direct methods | Extinction correction: none |
| C8H8Br2 | V = 885.7 (6) Å3 |
| Mr = 263.96 | Z = 4 |
| Monoclinic, P21/n | Mo Kα |
| a = 9.383 (4) Å | µ = 9.08 mm−1 |
| b = 7.918 (3) Å | T = 298 (2) K |
| c = 12.612 (5) Å | 0.20 × 0.12 × 0.10 mm |
| β = 109.041 (6)º |
| Bruker SMART CCD diffractometer | 1735 independent reflections |
| Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 1346 reflections with I > 2σ(I) |
| Tmin = 0.264, Tmax = 0.464 | Rint = 0.024 |
| 4542 measured reflections |
| R[F2 > 2σ(F2)] = 0.036 | 93 parameters |
| wR(F2) = 0.097 | H-atom parameters constrained |
| S = 1.07 | Δρmax = 0.69 e Å−3 |
| 1735 reflections | Δρmin = −0.34 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| Br1 | −0.20495 (5) | 0.21958 (7) | 0.68821 (4) | 0.0680 (2) | |
| Br2 | 0.06751 (6) | 0.44884 (7) | 0.87503 (4) | 0.0710 (2) | |
| C3 | 0.2076 (5) | 0.4319 (5) | 0.7077 (4) | 0.0524 (11) | |
| H3 | 0.2817 | 0.4961 | 0.7588 | 0.063* | |
| C1 | −0.0297 (4) | 0.2898 (5) | 0.6581 (3) | 0.0445 (9) | |
| C2 | 0.0831 (5) | 0.3833 (5) | 0.7341 (3) | 0.0460 (9) | |
| C5 | 0.1127 (5) | 0.2935 (5) | 0.5291 (4) | 0.0473 (10) | |
| C4 | 0.2257 (5) | 0.3871 (5) | 0.6057 (4) | 0.0513 (10) | |
| C6 | −0.0124 (5) | 0.2452 (5) | 0.5561 (3) | 0.0481 (10) | |
| H6 | −0.0870 | 0.1814 | 0.5051 | 0.058* | |
| C8 | 0.3680 (6) | 0.4447 (6) | 0.5815 (5) | 0.0670 (13) | |
| H8A | 0.3400 | 0.5149 | 0.5159 | 0.101* | |
| H8B | 0.4219 | 0.3476 | 0.5691 | 0.101* | |
| H8C | 0.4312 | 0.5075 | 0.6444 | 0.101* | |
| C7 | 0.1231 (6) | 0.2415 (6) | 0.4139 (4) | 0.0561 (11) | |
| H7A | 0.2090 | 0.1695 | 0.4246 | 0.084* | |
| H7B | 0.1336 | 0.3406 | 0.3732 | 0.084* | |
| H7C | 0.0332 | 0.1819 | 0.3721 | 0.084* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.0524 (3) | 0.0926 (4) | 0.0663 (3) | −0.0102 (2) | 0.0294 (2) | −0.0049 (3) |
| Br2 | 0.0788 (4) | 0.0802 (4) | 0.0534 (3) | 0.0011 (3) | 0.0206 (3) | −0.0182 (2) |
| C3 | 0.043 (2) | 0.044 (2) | 0.063 (3) | 0.0005 (18) | 0.008 (2) | 0.0017 (19) |
| C1 | 0.041 (2) | 0.047 (2) | 0.048 (2) | 0.0053 (17) | 0.0171 (18) | 0.0016 (17) |
| C2 | 0.046 (2) | 0.045 (2) | 0.044 (2) | 0.0071 (18) | 0.0109 (18) | −0.0016 (17) |
| C5 | 0.051 (2) | 0.043 (2) | 0.051 (2) | 0.0062 (19) | 0.0201 (19) | 0.0062 (18) |
| C4 | 0.043 (2) | 0.043 (2) | 0.072 (3) | 0.0071 (18) | 0.025 (2) | 0.010 (2) |
| C6 | 0.047 (2) | 0.051 (2) | 0.046 (2) | −0.0028 (18) | 0.0147 (19) | −0.0035 (17) |
| C8 | 0.055 (3) | 0.062 (3) | 0.095 (4) | −0.006 (2) | 0.040 (3) | 0.013 (3) |
| C7 | 0.064 (3) | 0.068 (3) | 0.048 (2) | 0.006 (2) | 0.034 (2) | 0.008 (2) |
| Br1—C1 | 1.889 (4) | C5—C7 | 1.544 (6) |
| Br2—C2 | 1.902 (4) | C4—C8 | 1.532 (6) |
| C3—C2 | 1.371 (6) | C6—H6 | 0.9300 |
| C3—C4 | 1.398 (6) | C8—H8A | 0.9600 |
| C3—H3 | 0.9300 | C8—H8B | 0.9600 |
| C1—C2 | 1.387 (6) | C8—H8C | 0.9600 |
| C1—C6 | 1.393 (6) | C7—H7A | 0.9600 |
| C5—C6 | 1.380 (6) | C7—H7B | 0.9600 |
| C5—C4 | 1.392 (6) | C7—H7C | 0.9600 |
| C2—C3—C4 | 121.5 (4) | C5—C6—C1 | 121.5 (4) |
| C2—C3—H3 | 119.3 | C5—C6—H6 | 119.2 |
| C4—C3—H3 | 119.3 | C1—C6—H6 | 119.2 |
| C2—C1—C6 | 118.8 (4) | C4—C8—H8A | 109.5 |
| C2—C1—Br1 | 122.4 (3) | C4—C8—H8B | 109.5 |
| C6—C1—Br1 | 118.8 (3) | H8A—C8—H8B | 109.5 |
| C3—C2—C1 | 120.0 (4) | C4—C8—H8C | 109.5 |
| C3—C2—Br2 | 118.8 (3) | H8A—C8—H8C | 109.5 |
| C1—C2—Br2 | 121.2 (3) | H8B—C8—H8C | 109.5 |
| C6—C5—C4 | 119.5 (4) | C5—C7—H7A | 109.5 |
| C6—C5—C7 | 118.6 (4) | C5—C7—H7B | 109.5 |
| C4—C5—C7 | 121.9 (4) | H7A—C7—H7B | 109.5 |
| C5—C4—C3 | 118.7 (4) | C5—C7—H7C | 109.5 |
| C5—C4—C8 | 122.4 (4) | H7A—C7—H7C | 109.5 |
| C3—C4—C8 | 118.9 (4) | H7B—C7—H7C | 109.5 |
| Br1—C1 | 1.889 (4) | C5—C7 | 1.544 (6) |
| Br2—C2 | 1.902 (4) | C4—C8 | 1.532 (6) |
| C2—C1—Br1 | 122.4 (3) | C4—C5—C7 | 121.9 (4) |
| C1—C2—Br2 | 121.2 (3) | C5—C4—C8 | 122.4 (4) |
The author gratefully acknowledges the support of Jingchu University of Technology and Wuhan University for the data collection.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Lawson, D. W., McOmie, J. F. W. & West, D. E. (1968). J. Chem. Soc. 2, 2414–2415.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (2000). SHELXTL. Version 6.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Siemens (1994). SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Siemens (1996). SMART and XPREP. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Skakle, J. M. S., et al. (2006).
Stoddart, J. F. (1989). Annu. Rep. Prog. Chem. B86, 353–387.
Molecules which possess novel belt-like and cage-like structures have played a central role in the development of supramolecular chemistry (Stoddart, 1989). Since maleimide derivatives are used frequently as the dienophiles in Diels-Alder cycloadditions, we are investigating methods of incorporating the maleimide moiety into 2-amino-1,2,3-triazolequinone derivatives. Considering the strategy synthetic in where the compound (I) it is used like precursor, we report here the structrure of (I), Fig.1.