(S,E)-3-[(2-Hy­droxy­benzyl­idene)amino]-2-(2-hy­droxy­phen­yl)-2,3-dihydro­quinazolin-4(1H)-one

Daniel Tinguiano; Adama Sy; Ibrahima Elhadj Thiam; Mohamed Gaye; Pascal Retailleau

doi:10.1107/S1600536812030012

. 2012 Jul 7;68(Pt 8):o2374–o2375. doi: 10.1107/S1600536812030012

(S,E)-3-[(2-Hydroxybenzylidene)amino]-2-(2-hydroxyphenyl)-2,3-dihydroquinazolin-4(1H)-one

Daniel Tinguiano ^a, Adama Sy ^a, Ibrahima Elhadj Thiam ^a, Mohamed Gaye ^a,^*, Pascal Retailleau ^b

PMCID: PMC3414304 PMID: 22904837

Abstract

In the title compound, C₂₁H₁₇N₃O₃, the dihydroquinazoline ring adopts a screw-boat conformation and its stereogenic C atom has an S configuration. The dihedral angle between the mean planes of the two hydroxyphenyl rings is 86.61 (12)°. The amino H atom forms an intramolecular hydrogen bond with a phenol O atom, while the hydrazine N atom acts as an acceptor for the H atom of the other phenol group. In the crystal, O—H⋯N and O—H⋯O hydrogen bonds and weak C—H⋯centroid(π-ring) intermolecular interactions are observed, forming chains along [1-10] and [110].

Related literature

For related structures and their biological properties, see: Rádl et al. (2000 ▶); Andries et al. (2005 ▶); Alagarsamy et al. (2006 ▶); Ghorab et al. (2007 ▶); El-Azab et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For determination of the absolute configuration, see: Flack (1983 ▶); Hooft et al. (2008 ▶).

Experimental

Crystal data

C₂₁H₁₇N₃O₃
M _r = 359.38
Orthorhombic,
a = 13.344 (15) Å
b = 10.693 (14) Å
c = 23.537 (13) Å
V = 3358 (6) Å³
Z = 8
Cu Kα radiation
μ = 0.79 mm⁻¹
T = 193 K
0.41 × 0.34 × 0.16 mm

Data collection

Rigaku RAPID II R-AXIS conversion diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.720, T _max = 0.889
15117 measured reflections
2947 independent reflections
2758 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.098
S = 1.07
2947 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), with 1258 Friedel pairs
Flack parameter: 0.0 (2)

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) interfaced by CRYSTALBUILDER (Welter, 2006 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030012/jj2144sup1.cif

e-68-o2374-sup1.cif^{(28.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030012/jj2144Isup2.hkl

e-68-o2374-Isup2.hkl^{(144.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812030012/jj2144Isup3.cml

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

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

Cg3 is the centroid of the C16–C21 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯N3	0.84	1.95	2.704 (4)	148
O2—H2O⋯O1ⁱ	0.84	1.73	2.555 (3)	168
C4—H4⋯Cg3ⁱⁱ	0.93	2.64	3.546 (5)	160
C5—H5⋯Cg3ⁱⁱⁱ	0.93	2.91	3.705 (5)	141

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

supplementary crystallographic information

Comment

Quinazolinone derivatives give rise to a large spectrum of biological properties such as analgesic (Rádl et al., 2000), antitubercular (Andries et al., 2005), antibacterial (Alagarsamy et al., 2006), anticancer activities (Ghorab et al., 2007) and anti-convulsant activity (El-Azab et al., 2010). We report here the crystal structure of the title compound, (I), and its absolute configuration. In the asymmetric unit of (I), the dihydroquinazolin ring adopts a screw-boat conformation with puckering parameters Q, θ, and φ of 0.4408 (18) Å, 64.1 (2)° and 41.9 (3)°, respectively (Cremer & Pople, 1975). The compound assumes an E configuration about the C═N double bond and its stereogenic C atom has an S configuration (Flack, 1983; Hooft et al., 2008) (Fig. 1). The amino H atom forms an intramolecular hydrogen bond with a phenolic O atom while the hydrazino N acts as acceptor for the H atom of the other phenolic group. The dihedral angle between the 2-hydroxyphenyl rings is 86.61 (12)°. O—H···N and O—H···O hydrogen bonds and weak C—H···Cgπ-ring intermolecular interactions are observed (Table 1) forming chains along [110] and [110] showing a corrugated layered structure in the ab plane which contributes to crystal packing stability (Fig. 2).

Experimental

o-Aminobenzoylhydrazine (0.302 g, 2 mmol) was dissolved in 5 ml ethanol and salicylaldehyde (0.488 g, 4 mmol) was added with thorough shaking. The mixture was heated under reflux during 2 h. On cooling, crystals that separated from the yellow solution were filtered off and recrystallized in methanol. Crystals suitable for X-ray analysis were obtained after 2 d. Yield: 73.5%. Anal. Calc. for [C₂₁H₁₇N₃O₃] (%): C, 70.18; H, 4.77; N, 11.69. Found: C, 70.16; H, 4.75; N, 11.71.