5′-Methyl-4′-oxo-7′-phenyl-3′,4′-dihydro-1′H-spiro­[cyclo­hexane-1,2′-quinazoline]-8′-carbonitrile

Jianhong Tang; Daxin Shi; Liupan Yan; Xuan Liu; Jiarong Li

doi:10.1107/S160053681102188X

. 2011 Jun 18;67(Pt 7):o1672. doi: 10.1107/S160053681102188X

5′-Methyl-4′-oxo-7′-phenyl-3′,4′-dihydro-1′H-spiro[cyclohexane-1,2′-quinazoline]-8′-carbonitrile

Jianhong Tang ^a,^b, Daxin Shi ^a, Liupan Yan ^a, Xuan Liu ^a, Jiarong Li ^a,^*

PMCID: PMC3152013 PMID: 21837071

Abstract

The title compound, C₂₁H₂₁N₃O, was obtained by cyclocondensation of 3-amino-5-methyl-[1,1′-biphenyl]-2,4-dicarbonitrile with cyclohexanone. The six-membered 1,3-diaza ring assumes an envelope conformation [with the flap atom displaced by 0.511 (7) Å from the plane through the other ring atoms] and the cyclohexane ring displays a chair conformation. The dihedral angle between the aromatic rings is 42.61 (7)°.In the crystal, the molecules form hydrogen-bonded bands along [011].

Related literature

For the medicinal and biological properities of dihydroquinazolin-4(3H)-one derivatives, see: Deng et al. (2000 ▶); Chenard et al. (2000 ▶); Bertrand et al. (2001 ▶); Welch et al. (2001 ▶). For a related structure, see Zhang et al. (2008 ▶)

Experimental

Crystal data

C₂₁H₂₁N₃O
M _r = 331.41
Triclinic,
a = 7.1824 (15) Å
b = 11.233 (3) Å
c = 11.430 (3) Å
α = 101.858 (8)°
β = 93.794 (9)°
γ = 104.606 (9)°
V = 866.6 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 153 K
0.35 × 0.27 × 0.27 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
9387 measured reflections
4521 independent reflections
3511 reflections with I > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.117
S = 1.00
4521 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrystalClear (Rigaku, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681102188X/ld2014sup1.cif

e-67-o1672-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102188X/ld2014Isup2.hkl

e-67-o1672-Isup2.hkl^{(221.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102188X/ld2014Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯Olⁱ	0.920 (17)	1.998 (14)	2.9010 (17)	171.68 (14)
N1—H1N⋯N3ⁱⁱ	0.875 (18)	2.281 (14)	3.1188 (19)	160.24 (15)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors thank Beijing Institute of Technology for the X-ray diffraction analysis.

supplementary crystallographic information

Comment

The molecular structure of (I) is represented on Fig. 1. The 1,3-diaza ring exists in an envelope conformation with its C6 atom displaced by 0.511 (7)Å from the rest of the atoms of the ring (planar within 0.025 (1) Å). The geometry of the fused rings compares well with the related spiro[cyclopentane-1,2'(1'H)-quinazolin]-4'(3')-one] (Zhang et al., 2008). The crystal packing is stabilized by intermolecular N—H···O and N—H···N hydrogen bonds forming alternating 8- and 12-membered centrosymmetric rings along [0 1 1] direction.

Experimental

3-Amino-5-methyl-biphenyl-2,4-dicarbonitrile (0.1 mmol) was added to a mixture of cyclohexanone (3 ml) and sodium hydroxide (0.03 mmol). The reagents were heated at 373 K for 1.5 h. The reaction mixture was cooled to room temperature with water (15 ml) and then filtered to give the title compound. The product was recrystallizated from a mixed solvent (ethanol:petroleum ether 1:3) to give pale-yellow crystals.

M.p. 572–573 K. Spectra data: IR (KBr): 3329, 3067, 2934, 2221,1660, 1560, 1403, 697 cm^-1; ¹H-NMR(DMSO, p.p.m.):1.34–1.85 (10H, m, C₅H₁₀), 2.64 (3H, d, J = 1.4 Hz, CH₃), 6.42(1H, s, NH), 6.71 (1H, s, ArH), 7.49–7.53 (5H, m, ArH), 8.26 (1H, s, NH); ESI-MS m/z: [M+H]⁺ 332.1; C₂₁H₂₁N₃O:calcd. C 76.11, H 6.39, N 12.68; found C 76.12, H 6.55, N 12.06.