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Acta Cryst. (2007). E63, o3675    [ doi:10.1107/S1600536807036975 ]

2-(4-Bromophenyl)-3-phenylbenzo[f]quinoline

X.-S. Wang, Q. Li, M.-M. Zhang and S.-J. Tu

Abstract top

The title compound, C25H16BrN, was synthesized by the reaction of N-arylidenenaphthalen-2-amine and phenylacetaldehyde in the presence of iodine. In the molecular structure, the benzoquinoline ring system makes dihedral angles of 61.1 (1) and 39.8 (1)°, respectively, with the phenyl and bromophenyl rings. The dihedral angle between these rings is 57.6 (1)°.

Comment top

Quinoline and its derivatives represent an important class of nitrogen-containing heterocycles as they constitute useful intermediates in organic synthesis and are useful dyes (Brock et al., 1999). They are well known in the pharmaceutical industry and have been shown to possess a broad spectrum of biological activities including antiasthmatic activity (Sawada et al., 2004), anti-inflammatory activity (Fokialakis et al., 2002), antimalarial activity (Fossa et al., 2002) and anthelmintic agents (Sakata et al., 1988). We report here the crystal structure of the title compound, (I).

In (I), the benzoquinoline ring system (C1—C5/N1/C18—C25) makes dihedral angles of 61.1 (1) and 39.8 (1)° with the phenyl (C12—C17) and benzene (C6—C11) rings, respectively. The dihedral angle between the phenyl (C12—C17) and benzene (C6—C11) rings is 57.6 (1)°. There is no intermolecular hydrogen bond in the crystal.

Related literature top

For related literature, see: Brock et al. (1999); Fokialakis et al. (2002); Fossa et al. (2002); Sakata et al. (1988); Sawada et al. (2004).

Experimental top

The title compound was prepared by the reaction of N-arylidenenaphthalen-2-amine (0.62 g, 2 mmol) and phenylacetaldehyde (0.24 g, 2 mmol) in the presence of iodine (0.05 g) in THF at 340 K for 5 h (yield 72%; m.p. 478–480 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a DMF solution.

Elemental analysis calculated: C 73.18, H 3.93, N, 3.41%; found: C 73.25, H 3.88, N 3.20%. 1H NMR (DMSO-d6): 7.38 (d, J = 8.4 Hz, 2H, ArH), 7.39 (s, 5H, ArH), 7.52 (d, J = 8.4 Hz, 2H, ArH), 7.74–7.76 (m, 2H, ArH), 7.99 (d, J = 8.8 Hz, 1H, ArH), 8.09–8.11 (m, 1H, ArH), 8.17 (d, J = 8.8 Hz, 1H, ArH), 9.19 (d, J = 7.6 Hz, 1H, ArH), 9.21 (s, 1H, ArH); IR (cm−1): 3056(ArH), 1678(C=N), 1603, 1584, 1566, 1487, 1472, 1431(phenyl ring).

Refinement top

The H atoms were calculated geometrically (C—H = 0.95 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (please check); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
2-(4-Bromophenyl)-3-phenylbenzo[f]quinoline top
Crystal data top
C25H16BrNF000 = 832
Mr = 410.30Dx = 1.497 Mg m−3
Monoclinic, P21/cMelting point: 478-480 K
Hall symbol: -P 2ybcMo Kα radiation
λ = 0.71070 Å
a = 12.704 (2) ÅCell parameters from 6717 reflections
b = 9.4917 (14) Åθ = 3.0–25.3º
c = 15.142 (3) ŵ = 2.27 mm−1
β = 94.612 (4)ºT = 193 (2) K
V = 1819.9 (5) Å3Block, colorless
Z = 40.78 × 0.55 × 0.17 mm
Data collection top
Rigaku Mercury CCD
diffractometer		3336 independent reflections
Radiation source: fine-focus sealed tube3034 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.042
Detector resolution: 7.31 pixels mm-1θmax = 25.4º
T = 193(2) Kθmin = 3.0º
ω scansh = −15→13
Absorption correction: multi-scan
(Jacobson, 1998)		k = −11→11
Tmin = 0.298, Tmax = 0.679l = −18→17
17280 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.084  w = 1/[σ2(Fo2) + (0.0252P)2 + 1.5016P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max < 0.001
3336 reflectionsΔρmax = 0.36 e Å−3
245 parametersΔρmin = −0.29 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C25H16BrNV = 1819.9 (5) Å3
Mr = 410.30Z = 4
Monoclinic, P21/cMo Kα
a = 12.704 (2) ŵ = 2.27 mm−1
b = 9.4917 (14) ÅT = 193 (2) K
c = 15.142 (3) Å0.78 × 0.55 × 0.17 mm
β = 94.612 (4)º
Data collection top
Rigaku Mercury CCD
diffractometer		3336 independent reflections
Absorption correction: multi-scan
(Jacobson, 1998)		3034 reflections with I > 2σ(I)
Tmin = 0.298, Tmax = 0.679Rint = 0.042
17280 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042245 parameters
wR(F2) = 0.084H-atom parameters constrained
S = 1.17Δρmax = 0.36 e Å−3
3336 reflectionsΔρmin = −0.29 e Å−3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.41136 (3)−0.18517 (3)0.83655 (2)0.04218 (13)
N10.03956 (17)0.1754 (2)0.57827 (14)0.0277 (5)
C10.1407 (2)0.1676 (3)0.56232 (17)0.0257 (6)
C20.1811 (2)0.2330 (3)0.48741 (17)0.0245 (6)
C30.1113 (2)0.3102 (3)0.43206 (17)0.0270 (6)
H30.13670.35690.38250.032*
C40.0041 (2)0.3215 (3)0.44696 (17)0.0247 (6)
C5−0.0276 (2)0.2501 (3)0.52243 (17)0.0268 (6)
C60.2081 (2)0.0849 (3)0.62874 (17)0.0258 (6)
C70.1673 (2)−0.0381 (3)0.66346 (18)0.0294 (6)
H70.0978−0.06770.64380.035*
C80.2262 (2)−0.1175 (3)0.72588 (18)0.0303 (6)
H80.1980−0.20120.74910.036*
C90.3270 (2)−0.0729 (3)0.75395 (17)0.0286 (6)
C100.3691 (2)0.0492 (3)0.72268 (18)0.0304 (6)
H100.43780.07930.74380.036*
C110.3088 (2)0.1277 (3)0.65955 (17)0.0271 (6)
H110.33710.21190.63720.033*
C120.2918 (2)0.2181 (3)0.46368 (17)0.0251 (6)
C130.3338 (2)0.0866 (3)0.44567 (18)0.0312 (7)
H130.29250.00410.45130.037*
C140.4349 (2)0.0755 (3)0.41985 (19)0.0354 (7)
H140.4621−0.01450.40630.042*
C150.4972 (2)0.1933 (3)0.41337 (19)0.0339 (7)
H150.56740.18450.39660.041*
C160.4569 (2)0.3239 (3)0.43142 (19)0.0331 (7)
H160.49940.40560.42750.040*
C170.3545 (2)0.3359 (3)0.45528 (18)0.0294 (6)
H170.32660.42660.46610.035*
C18−0.1360 (2)0.2552 (3)0.54188 (19)0.0311 (7)
H18−0.15730.20860.59300.037*
C19−0.2081 (2)0.3251 (3)0.48871 (19)0.0325 (7)
H19−0.27940.32690.50310.039*
C20−0.1798 (2)0.3970 (3)0.41076 (18)0.0293 (6)
C21−0.2560 (2)0.4670 (3)0.35408 (19)0.0360 (7)
H21−0.32740.46870.36850.043*
C22−0.2291 (3)0.5324 (3)0.2787 (2)0.0408 (8)
H22−0.28150.57990.24150.049*
C23−0.1256 (3)0.5294 (4)0.2567 (2)0.0435 (8)
H23−0.10730.57360.20380.052*
C24−0.0491 (2)0.4632 (3)0.3106 (2)0.0389 (7)
H240.02170.46280.29460.047*
C25−0.0736 (2)0.3956 (3)0.38919 (17)0.0276 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0505 (2)0.0406 (2)0.03533 (19)0.01776 (15)0.00243 (14)0.00900 (15)
N10.0279 (13)0.0312 (13)0.0238 (12)−0.0001 (10)0.0016 (10)0.0020 (10)
C10.0287 (15)0.0247 (14)0.0237 (14)−0.0015 (11)0.0011 (12)−0.0027 (12)
C20.0261 (14)0.0255 (14)0.0219 (14)−0.0035 (11)0.0015 (11)−0.0030 (11)
C30.0311 (15)0.0282 (14)0.0216 (14)−0.0030 (12)0.0015 (12)0.0012 (12)
C40.0249 (14)0.0258 (14)0.0230 (14)−0.0012 (11)0.0004 (11)−0.0034 (12)
C50.0282 (15)0.0282 (15)0.0236 (14)−0.0028 (12)0.0002 (12)−0.0031 (12)
C60.0305 (15)0.0256 (14)0.0217 (14)0.0043 (12)0.0045 (12)−0.0017 (12)
C70.0334 (16)0.0292 (15)0.0260 (15)−0.0020 (12)0.0042 (12)−0.0014 (12)
C80.0439 (18)0.0227 (14)0.0254 (15)0.0043 (13)0.0086 (13)−0.0001 (12)
C90.0340 (16)0.0309 (15)0.0209 (14)0.0113 (13)0.0027 (12)0.0005 (12)
C100.0299 (16)0.0349 (16)0.0264 (15)0.0027 (12)0.0025 (12)−0.0009 (13)
C110.0320 (16)0.0261 (14)0.0233 (14)−0.0017 (12)0.0022 (12)0.0021 (12)
C120.0252 (14)0.0320 (15)0.0175 (13)−0.0002 (12)−0.0012 (11)0.0015 (12)
C130.0315 (16)0.0310 (16)0.0303 (15)−0.0037 (13)−0.0029 (13)−0.0039 (13)
C140.0339 (17)0.0361 (17)0.0360 (17)0.0065 (14)0.0015 (14)−0.0086 (14)
C150.0244 (15)0.0477 (19)0.0299 (15)0.0039 (14)0.0038 (12)−0.0037 (14)
C160.0331 (16)0.0351 (17)0.0318 (16)−0.0052 (13)0.0070 (13)0.0004 (13)
C170.0310 (16)0.0284 (15)0.0294 (15)0.0019 (12)0.0065 (13)0.0007 (12)
C180.0293 (16)0.0371 (16)0.0272 (15)−0.0006 (13)0.0043 (13)−0.0006 (13)
C190.0261 (15)0.0397 (17)0.0324 (16)0.0007 (13)0.0068 (13)−0.0073 (14)
C200.0298 (15)0.0301 (15)0.0273 (15)0.0039 (12)−0.0016 (12)−0.0083 (13)
C210.0328 (16)0.0414 (18)0.0332 (17)0.0085 (14)−0.0023 (13)−0.0060 (14)
C220.0439 (19)0.0441 (19)0.0324 (17)0.0140 (15)−0.0098 (14)−0.0032 (15)
C230.044 (2)0.050 (2)0.0352 (18)0.0071 (16)−0.0035 (15)0.0135 (15)
C240.0341 (17)0.0475 (19)0.0349 (17)−0.0005 (14)0.0011 (14)0.0095 (15)
C250.0286 (15)0.0284 (15)0.0252 (14)−0.0003 (12)−0.0022 (12)−0.0023 (12)
Geometric parameters (Å, °) top
Br1—C91.906 (3)C13—C141.376 (4)
N1—C11.328 (3)C13—H130.9500
N1—C51.353 (3)C14—C151.379 (4)
C1—C21.424 (4)C14—H140.9500
C1—C61.491 (4)C15—C161.376 (4)
C2—C31.380 (4)C15—H150.9500
C2—C121.485 (4)C16—C171.383 (4)
C3—C41.403 (4)C16—H160.9500
C3—H30.9500C17—H170.9500
C4—C51.415 (4)C18—C191.344 (4)
C4—C251.448 (4)C18—H180.9500
C5—C181.432 (4)C19—C201.434 (4)
C6—C111.387 (4)C19—H190.9500
C6—C71.398 (4)C20—C211.407 (4)
C7—C81.381 (4)C20—C251.414 (4)
C7—H70.9500C21—C221.366 (4)
C8—C91.383 (4)C21—H210.9500
C8—H80.9500C22—C231.383 (4)
C9—C101.376 (4)C22—H220.9500
C10—C111.392 (4)C23—C241.370 (4)
C10—H100.9500C23—H230.9500
C11—H110.9500C24—C251.409 (4)
C12—C171.385 (4)C24—H240.9500
C12—C131.393 (4)
C1—N1—C5119.1 (2)C14—C13—H13119.8
N1—C1—C2122.5 (2)C12—C13—H13119.8
N1—C1—C6114.7 (2)C13—C14—C15120.8 (3)
C2—C1—C6122.8 (2)C13—C14—H14119.6
C3—C2—C1117.4 (2)C15—C14—H14119.6
C3—C2—C12118.5 (2)C16—C15—C14119.4 (3)
C1—C2—C12124.1 (2)C16—C15—H15120.3
C2—C3—C4121.8 (2)C14—C15—H15120.3
C2—C3—H3119.1C15—C16—C17119.9 (3)
C4—C3—H3119.1C15—C16—H16120.0
C3—C4—C5115.9 (2)C17—C16—H16120.0
C3—C4—C25124.3 (2)C16—C17—C12121.2 (3)
C5—C4—C25119.7 (2)C16—C17—H17119.4
N1—C5—C4123.3 (2)C12—C17—H17119.4
N1—C5—C18117.3 (2)C19—C18—C5120.9 (3)
C4—C5—C18119.4 (2)C19—C18—H18119.6
C11—C6—C7118.6 (3)C5—C18—H18119.6
C11—C6—C1122.5 (2)C18—C19—C20121.6 (3)
C7—C6—C1118.9 (2)C18—C19—H19119.2
C8—C7—C6121.0 (3)C20—C19—H19119.2
C8—C7—H7119.5C21—C20—C25119.1 (3)
C6—C7—H7119.5C21—C20—C19121.4 (3)
C7—C8—C9118.8 (3)C25—C20—C19119.5 (3)
C7—C8—H8120.6C22—C21—C20121.2 (3)
C9—C8—H8120.6C22—C21—H21119.4
C10—C9—C8121.8 (3)C20—C21—H21119.4
C10—C9—Br1118.9 (2)C21—C22—C23119.8 (3)
C8—C9—Br1119.3 (2)C21—C22—H22120.1
C9—C10—C11118.7 (3)C23—C22—H22120.1
C9—C10—H10120.7C24—C23—C22120.6 (3)
C11—C10—H10120.7C24—C23—H23119.7
C6—C11—C10121.1 (3)C22—C23—H23119.7
C6—C11—H11119.5C23—C24—C25121.2 (3)
C10—C11—H11119.5C23—C24—H24119.4
C17—C12—C13118.2 (2)C25—C24—H24119.4
C17—C12—C2120.5 (2)C24—C25—C20118.1 (3)
C13—C12—C2121.2 (2)C24—C25—C4123.1 (3)
C14—C13—C12120.4 (3)C20—C25—C4118.8 (2)
C5—N1—C1—C2−1.2 (4)C1—C2—C12—C17−122.9 (3)
C5—N1—C1—C6179.0 (2)C3—C2—C12—C13−117.5 (3)
N1—C1—C2—C32.1 (4)C1—C2—C12—C1359.9 (4)
C6—C1—C2—C3−178.2 (2)C17—C12—C13—C14−0.3 (4)
N1—C1—C2—C12−175.3 (2)C2—C12—C13—C14177.0 (3)
C6—C1—C2—C124.4 (4)C12—C13—C14—C151.6 (4)
C1—C2—C3—C4−1.7 (4)C13—C14—C15—C16−1.2 (4)
C12—C2—C3—C4175.9 (2)C14—C15—C16—C17−0.4 (4)
C2—C3—C4—C50.5 (4)C15—C16—C17—C121.7 (4)
C2—C3—C4—C25−177.1 (3)C13—C12—C17—C16−1.3 (4)
C1—N1—C5—C40.0 (4)C2—C12—C17—C16−178.6 (2)
C1—N1—C5—C18179.7 (2)N1—C5—C18—C19−178.8 (3)
C3—C4—C5—N10.4 (4)C4—C5—C18—C191.0 (4)
C25—C4—C5—N1178.2 (2)C5—C18—C19—C200.1 (4)
C3—C4—C5—C18−179.4 (2)C18—C19—C20—C21178.3 (3)
C25—C4—C5—C18−1.6 (4)C18—C19—C20—C25−0.4 (4)
N1—C1—C6—C11−138.9 (3)C25—C20—C21—C220.4 (4)
C2—C1—C6—C1141.3 (4)C19—C20—C21—C22−178.4 (3)
N1—C1—C6—C739.0 (3)C20—C21—C22—C230.6 (5)
C2—C1—C6—C7−140.8 (3)C21—C22—C23—C24−1.1 (5)
C11—C6—C7—C8−1.2 (4)C22—C23—C24—C250.5 (5)
C1—C6—C7—C8−179.3 (2)C23—C24—C25—C200.5 (4)
C6—C7—C8—C90.2 (4)C23—C24—C25—C4178.5 (3)
C7—C8—C9—C101.2 (4)C21—C20—C25—C24−0.9 (4)
C7—C8—C9—Br1−177.56 (19)C19—C20—C25—C24177.9 (3)
C8—C9—C10—C11−1.5 (4)C21—C20—C25—C4−179.0 (2)
Br1—C9—C10—C11177.3 (2)C19—C20—C25—C4−0.2 (4)
C7—C6—C11—C101.0 (4)C3—C4—C25—C240.8 (4)
C1—C6—C11—C10178.9 (2)C5—C4—C25—C24−176.8 (3)
C9—C10—C11—C60.4 (4)C3—C4—C25—C20178.8 (3)
C3—C2—C12—C1759.8 (3)C5—C4—C25—C201.2 (4)
Acknowledgements top

We thank the Foundation of Natural Sciences of Xuzhou Normal University (06XLA10 and 06PYL04) for financial support.

references
References top

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