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

Xuan Liu; Daxin Shi; Jianhong Tang; Deli Yang; Jiarong Li

doi:10.1107/S1600536811026948

. 2011 Jul 13;67(Pt 8):o2016. doi: 10.1107/S1600536811026948

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

Xuan Liu ^a, Daxin Shi ^a, Jianhong Tang ^a,^b, Deli Yang ^a, Jiarong Li ^a,^*

PMCID: PMC3213469 PMID: 22091048

Abstract

In the title compound, C₂₁H₂₁N₃OS·C₃H₇NO, the carbonitrile molecule is built up of two fused six-membered rings and one six-membered ring linked through a spiro C atom. The 1,3-diaza ring adopts an envelope conformation and the cyclohexane ring adopts a chair conformation. The dihedral angle between the aromatic rings is 46.7 (3)°. In the crystal, the components are linked by N—H⋯O hydrogen bonds.

Related literature

For medicinal and biological properties of dihydroquinazolin-3H-4-one derivatives, see: Alagarsamy & Murugesan (2007 ▶); Wang et al. (2007 ▶); Jatav et al. (2008 ▶); Markosyan et al. (2010 ▶). For a related structure, see Zhang et al. (2008 ▶).

Experimental

Crystal data

C₂₁H₂₁N₃OS·C₃H₇NO
M _r = 436.56
Triclinic,
a = 9.415 (3) Å
b = 10.615 (3) Å
c = 12.037 (3) Å
α = 95.092 (3)°
β = 98.156 (4)°
γ = 109.833 (3)°
V = 1108.0 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 153 K
0.31 × 0.31 × 0.12 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.947, T _max = 0.979
11758 measured reflections
5754 independent reflections
4274 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.117
S = 1.00
5754 reflections
291 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008) ▶; 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/S1600536811026948/aa2012sup1.cif

e-67-o2016-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026948/aa2012Isup2.hkl

e-67-o2016-Isup2.hkl^{(281.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026948/aa2012Isup3.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
N1—H11⋯N3ⁱ	0.838 (10)	2.328 (14)	3.120 (2)	157.96 (3)
N2—H21⋯O1ⁱⁱ	0.886 (10)	2.044 (18)	2.927 (3)	174.94 (3)

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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 5'-methylthio-4'-oxo-7'-phenyl-3',4'-dihydro-1'H-spiro[cyclohexane-1, 2'-quinazoline]-8'-carbonitrile(I) is built up with one six membered ring and two fused six membered rings and a six membered ring linked through a spiro C atom (Fig. 1). The ring of C1, C2, C3, C4, C5, C6 exists in an chair conformation, and the C6 atom displaced by 0.647 (6)Å from the ring of C1, C2, C4, C5 (planar within 0.019 (5) Å), while C3 atom displaced by 0.669 (8) Å. The 1,3-diaza ring exists in an envelope conformation, and the C6 atom displaced by 0.476 (5)Å from the rest of the atoms of the 1,3-diaza ring (planar within 0.013 (5) Å). The dihedral angle between the plane (C14, C15, C16, C17, C18, C19) and the plane (C8, C9, C10, C11, C12, C13) is 46.7 (3)°. The angle between C9, S1, C20 is 102.83 (8) Å. The geometry of the fused rings compares well with the related spiro[cyclopentane-1,2'(1'H)-quinazolin]-4'(3'H)-one] (Zhang et al., 2008). The crystal packing is stabilized by intermolecular N—H···O and N—H···N bonds.

Experimental

To a solution of cyclohexanone (3 ml) and sodium hydroxide (0.3 mmol) were added 3-amino-5-(methylthio)biphenyl-2,4-dicarbonitrile (0.1 mmol). The mixture was heated at 373 K for 2.0 h. The reaction mixture was cooled with ice water (20 ml) and then filtered to give the title compound. The product was recrystallizated from a mixed solvent (ethanol:N,N-dimethylformamide 1:3) to obtain colorless single crystals. M.p. 572–573 K. Spectra data: IR (KBr): 3317, 3219, 2933, 2216, 1650, 1585, 1550, 1413, 771, 709 cm^-1. ¹H-NMR (DMSO-d₆, p.p.m.): 0.92–1.84 (10H, m, C₅H₁₀), 2.38 (3H, s, SCH₃), 6.50(1H, s, NH), 6.61 (1H, s, ArH), 7.50–7.61 (5H, m, ArH), 8.29 (1H, s, NH). ESI-MS m/z: [M+H]⁺ 364.1. C₂₁H₂₁N₃OS: calcd. % C 69.39, H 5.82, N 11.56; found % C 69.28, H 5.68, N 11.31.