Acta Cryst. (2008). E64, o1117 [ doi:10.1107/S1600536808014591 ]
The non-H atoms of the title molecule, C10H8BrNO, are essentially coplanar. In the crystal structure, molecules are linked by weak intermolecular C-H
![[pi]](/logos/entities/pi_rmgif.gif)
(arene) interactions, forming one-dimensional chains along the a axis.
X-ray quality crystals were obtained by evaporation of a solution of the title compound (ECA International Corporation, Palatine, Illinois, USA) in chloroform.
H atoms were placed in calculated positions with C—H = 0.95Å (aryl) and 0.98Å (methyl) and were included in the refinement in the riding-model approximation with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C) for methyl H atoms.
Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003) and SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./pv2082fig1thm.gif)
| Fig. 1. Molecular structure showing 30% probability displacement ellipsoids (arbitrary spheres for H atoms). |
![[Figure 2]](./pv2082fig2thm.gif)
| Fig. 2. Part of the crystal structure showing weak C—H···π(arene) interactions as dashed lines. |
| C10H8BrNO | F000 = 472 |
| Mr = 238.08 | Dx = 1.773 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 6134 reflections |
| a = 5.1615 (1) Å | θ = 2.9–27.5º |
| b = 12.1337 (6) Å | µ = 4.56 mm−1 |
| c = 14.2436 (7) Å | T = 150 (1) K |
| V = 892.05 (6) Å3 | Needle, colourless |
| Z = 4 | 0.30 × 0.12 × 0.11 mm |
| Nonius KappaCCD diffractometer | 2026 independent reflections |
| Radiation source: fine-focus sealed tube | 1872 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.036 |
| Detector resolution: 9 pixels mm-1 | θmax = 27.5º |
| T = 150(2) K | θmin = 2.9º |
| φ scans and ω scans with κ offsets | h = −5→6 |
| Absorption correction: multi-scan (SORTAV; Blessing 1995) | k = −14→15 |
| Tmin = 0.545, Tmax = 0.607 | l = −18→18 |
| 6134 measured reflections |
| Refinement on F2 | H-atom parameters constrained |
| Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0306P)2 + 0.0333P] where P = (Fo2 + 2Fc2)/3 |
| R[F2 > 2σ(F2)] = 0.028 | (Δ/σ)max = 0.001 |
| wR(F2) = 0.059 | Δρmax = 0.38 e Å−3 |
| S = 1.01 | Δρmin = −0.40 e Å−3 |
| 2026 reflections | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 120 parameters | Extinction coefficient: 0.0062 (8) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 815 Friedel pairs |
| Secondary atom site location: difference Fourier map | Flack parameter: −0.017 (11) |
| Hydrogen site location: inferred from neighbouring sites |
| C10H8BrNO | V = 892.05 (6) Å3 |
| Mr = 238.08 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα |
| a = 5.1615 (1) Å | µ = 4.56 mm−1 |
| b = 12.1337 (6) Å | T = 150 (1) K |
| c = 14.2436 (7) Å | 0.30 × 0.12 × 0.11 mm |
| Nonius KappaCCD diffractometer | 2026 independent reflections |
| Absorption correction: multi-scan (SORTAV; Blessing 1995) | 1872 reflections with I > 2σ(I) |
| Tmin = 0.545, Tmax = 0.607 | Rint = 0.036 |
| 6134 measured reflections |
| R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
| wR(F2) = 0.059 | Δρmax = 0.38 e Å−3 |
| S = 1.01 | Δρmin = −0.40 e Å−3 |
| 2026 reflections | Absolute structure: Flack (1983), 815 Friedel pairs |
| 120 parameters | Flack parameter: −0.017 (11) |
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 > σ(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 | 1.02034 (5) | 0.36147 (2) | 0.509948 (18) | 0.02940 (11) | |
| O1 | 0.1007 (3) | 0.62674 (16) | 0.72708 (14) | 0.0259 (4) | |
| N1 | 0.4260 (4) | 0.64140 (17) | 0.58326 (14) | 0.0233 (4) | |
| C1 | 0.5884 (5) | 0.6481 (2) | 0.51287 (18) | 0.0278 (6) | |
| H1A | 0.5819 | 0.7126 | 0.4752 | 0.033* | |
| C2 | 0.7717 (5) | 0.5671 (2) | 0.48878 (19) | 0.0268 (6) | |
| H2A | 0.8842 | 0.5768 | 0.4366 | 0.032* | |
| C3 | 0.7833 (5) | 0.4746 (2) | 0.54217 (19) | 0.0239 (6) | |
| C4 | 0.6190 (5) | 0.4611 (2) | 0.62176 (17) | 0.0188 (5) | |
| C5 | 0.6239 (5) | 0.3694 (2) | 0.68244 (18) | 0.0232 (6) | |
| H5A | 0.7429 | 0.3109 | 0.6718 | 0.028* | |
| C6 | 0.4556 (5) | 0.3650 (2) | 0.75705 (17) | 0.0243 (6) | |
| H6A | 0.4624 | 0.3038 | 0.7986 | 0.029* | |
| C7 | 0.2739 (5) | 0.4487 (2) | 0.77325 (18) | 0.0235 (6) | |
| H7A | 0.1558 | 0.4424 | 0.8241 | 0.028* | |
| C8 | 0.2656 (5) | 0.5400 (2) | 0.71586 (17) | 0.0195 (5) | |
| C9 | 0.4408 (5) | 0.54916 (19) | 0.63810 (16) | 0.0199 (5) | |
| C10 | −0.0731 (5) | 0.6201 (2) | 0.80535 (18) | 0.0271 (7) | |
| H10C | −0.1784 | 0.6872 | 0.8083 | 0.041* | |
| H10D | 0.0269 | 0.6126 | 0.8635 | 0.041* | |
| H10A | −0.1865 | 0.5559 | 0.7978 | 0.041* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Br1 | 0.02472 (15) | 0.03108 (16) | 0.03239 (16) | 0.00303 (10) | 0.00306 (11) | −0.00756 (11) |
| O1 | 0.0264 (10) | 0.0255 (11) | 0.0259 (10) | 0.0030 (8) | 0.0047 (7) | 0.0004 (8) |
| N1 | 0.0281 (10) | 0.0212 (11) | 0.0206 (11) | −0.0009 (9) | −0.0021 (8) | 0.0001 (10) |
| C1 | 0.0339 (13) | 0.0259 (14) | 0.0237 (14) | −0.0019 (10) | 0.0030 (10) | 0.0087 (14) |
| C2 | 0.0265 (12) | 0.0299 (14) | 0.0240 (14) | −0.0065 (10) | 0.0049 (12) | 0.0001 (13) |
| C3 | 0.0215 (13) | 0.0257 (14) | 0.0246 (15) | −0.0015 (10) | −0.0025 (10) | −0.0078 (12) |
| C4 | 0.0210 (13) | 0.0184 (13) | 0.0169 (13) | −0.0037 (9) | −0.0018 (9) | −0.0016 (11) |
| C5 | 0.0224 (12) | 0.0215 (14) | 0.0257 (14) | 0.0016 (11) | −0.0064 (10) | −0.0019 (12) |
| C6 | 0.0328 (15) | 0.0176 (13) | 0.0225 (13) | −0.0037 (13) | −0.0074 (11) | 0.0035 (11) |
| C7 | 0.0257 (14) | 0.0258 (15) | 0.0191 (14) | −0.0088 (11) | 0.0018 (11) | −0.0010 (11) |
| C8 | 0.0208 (13) | 0.0185 (13) | 0.0193 (13) | −0.0003 (10) | −0.0021 (10) | −0.0014 (11) |
| C9 | 0.0207 (12) | 0.0204 (13) | 0.0186 (12) | −0.0042 (10) | −0.0046 (10) | 0.0010 (10) |
| C10 | 0.0240 (14) | 0.0314 (17) | 0.0258 (15) | 0.0015 (12) | 0.0047 (11) | −0.0028 (12) |
| Br1—C3 | 1.895 (2) | C4—C9 | 1.429 (3) |
| O1—C8 | 1.362 (3) | C5—C6 | 1.374 (4) |
| O1—C10 | 1.433 (3) | C5—H5A | 0.9500 |
| N1—C1 | 1.309 (3) | C6—C7 | 1.402 (4) |
| N1—C9 | 1.367 (3) | C6—H6A | 0.9500 |
| C1—C2 | 1.407 (4) | C7—C8 | 1.378 (4) |
| C1—H1A | 0.9500 | C7—H7A | 0.9500 |
| C2—C3 | 1.357 (3) | C8—C9 | 1.434 (3) |
| C2—H2A | 0.9500 | C10—H10C | 0.9800 |
| C3—C4 | 1.425 (3) | C10—H10D | 0.9800 |
| C4—C5 | 1.409 (4) | C10—H10A | 0.9800 |
| C8—O1—C10 | 116.0 (2) | C5—C6—H6A | 119.3 |
| C1—N1—C9 | 116.9 (2) | C7—C6—H6A | 119.3 |
| N1—C1—C2 | 125.0 (2) | C8—C7—C6 | 120.4 (2) |
| N1—C1—H1A | 117.5 | C8—C7—H7A | 119.8 |
| C2—C1—H1A | 117.5 | C6—C7—H7A | 119.8 |
| C3—C2—C1 | 118.1 (2) | O1—C8—C7 | 124.8 (2) |
| C3—C2—H2A | 121.0 | O1—C8—C9 | 115.1 (2) |
| C1—C2—H2A | 121.0 | C7—C8—C9 | 120.0 (2) |
| C2—C3—C4 | 121.0 (2) | N1—C9—C4 | 123.7 (2) |
| C2—C3—Br1 | 119.4 (2) | N1—C9—C8 | 118.0 (2) |
| C4—C3—Br1 | 119.58 (19) | C4—C9—C8 | 118.3 (2) |
| C5—C4—C3 | 124.6 (2) | O1—C10—H10C | 109.5 |
| C5—C4—C9 | 120.1 (2) | O1—C10—H10D | 109.5 |
| C3—C4—C9 | 115.3 (2) | H10C—C10—H10D | 109.5 |
| C6—C5—C4 | 119.6 (3) | O1—C10—H10A | 109.5 |
| C6—C5—H5A | 120.2 | H10C—C10—H10A | 109.5 |
| C4—C5—H5A | 120.2 | H10D—C10—H10A | 109.5 |
| C5—C6—C7 | 121.5 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C10—H10A···Cgi | 0.98 | 2.66 | 3.531 (3) | 148 |
| Symmetry codes: (i) x−1, y, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C10—H10A···Cgi | 0.98 | 2.66 | 3.531 (3) | 148 |
| Symmetry codes: (i) x−1, y, z. |
We thank Dr Peter P. Antich and Dr Frederick J. Bonte for helpful discussions and support. Financial support for this work was provided by the Natural Sciences and Engineering Research Council of Canada (NSERC).
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Quinoline derivatatives are established chelating agents and also have applications as precursors for pesticides and pharmaceuticals (Michael, 2008). Our laboratories are pursuing the development of radiohalogenated 8-hydroxyquinoline derivatives for positron emission tomography (PET) and single photon emission computed tomography (SPECT), specifically to image extracellular glial deposition of amyloid plaque protein in Alzheimer's disease and matrix metalloproteinases in tumours (Kulkarni et al., 2006). 4-Bromo-8-methoxyquinoline, first reported by Irving & Pinnington (1957) may be used as a precursor for radiohalogenation reactions to prepare labelled 8-hydroxyquinoline-based PET or SPECT radiopharmaceuticals. To our surprise, neutral compounds bearing a 4-halogen substituted, 8-phenoxyquinoline core have not yet been studied by single-crystal X-ray crystallography. In the present study we report the crystal structure of the title compound at 150 K.
The non-hydrogen atoms of title molecule (Fig. 1), C10H8BrNO, are essentially co-planar (r.m.s. deviation of all non-H atoms = 0.0242 Å). In the crystal structure, molecules are linked by weak intermolecuar C—H···π(arene) interactions to form one-dimensional chains along the a axis (Fig. 2). There are no other hydrogen bonds or π···π stacking interactions.