4-(4-{[(2-Phenyl­quinazolin-4-yl)­oxy]methyl}-1H-1,2,3-triazol-1-yl)butan-1-ol hemihydrate

Abdelaaziz Ouahrouch; Hassan B Lazrek; Moha Taourirte; Mohamed El Azhari; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S1600536811027280

. 2011 Jul 13;67(Pt 8):o2029–o2030. doi: 10.1107/S1600536811027280

4-(4-{[(2-Phenylquinazolin-4-yl)oxy]methyl}-1H-1,2,3-triazol-1-yl)butan-1-ol hemihydrate

Abdelaaziz Ouahrouch ^a, Hassan B Lazrek ^b, Moha Taourirte ^a, Mohamed El Azhari ^c, Mohamed Saadi ^d, Lahcen El Ammari ^d,^*

PMCID: PMC3213479 PMID: 22091058

Abstract

The title compound, C₂₁H₂₁N₅O₂·0.5H₂O, has two fused six-membered rings linked to a benzene ring and to a triazole ring, which is connected to a butanol group. The quinazoline ring forms a dihedral angle of 7.88 (8)° with the benzene ring, while the triazole ring is approximately perpendicular to the benzene ring and to the quinazoline system, making dihedral angles of 84.38 (10) and 76.55 (8)°, respectively. The stereochemical arrangement of the butanol chain, with a C—C—C—C torsion angle of 178.34 (19)°, corresponds to an antiperiplanar conformation. However the position of the –OH group is split into two very close [O—O = 0.810(3) Å] positions of equal occupancy. The crystal structure features O—H⋯N and O—H⋯O hydrogen bonds, building an infinite three-dimensional network. The water molecule is located on a half-filled general position.

Related literature

For details of the synthesis, see: Krim et al. (2009 ▶); Mani Chandrika et al. (2010 ▶). For the biological activity of quinazolinone derivatives, see: Alvarez et al. (1994 ▶); Chan et al. (1997 ▶); De Clercq (1997 ▶, 2002 ▶); Dempcy & Skibo (1991 ▶); Gackenheimer et al. (1995 ▶).

Experimental

Crystal data

C₂₁H₂₁N₅O₂·0.5H₂O
M _r = 384.44
Monoclinic,
a = 11.359 (4) Å
b = 7.694 (3) Å
c = 22.817 (7) Å
β = 101.111 (16)°
V = 1956.9 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.55 × 0.31 × 0.28 mm

Data collection

Bruker X8 APEX Diffractometer
18195 measured reflections
3709 independent reflections
2879 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.127
S = 1.03
3709 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia,1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027280/fj2442sup1.cif

e-67-o2029-sup1.cif^{(30.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027280/fj2442Isup2.hkl

e-67-o2029-Isup2.hkl^{(181.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811027280/fj2442Isup3.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
O2B—H2B⋯N1ⁱ	0.86	2.08	2.935 (3)	170
O2A—H2A⋯O3Wⁱⁱ	0.86	1.90	2.757 (4)	176
O3W—H3WA⋯N3ⁱⁱⁱ	0.86	2.12	2.967 (3)	167
O3W—H3WB⋯N3	0.86	2.00	2.835 (3)	163

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

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

supplementary crystallographic information

Comment

The quinazolinone derivatives are an important class of compounds, as they are present in a large family of products with broad biological activities. For example: anticancers, diuretics, anti-inflammatories, anticonvulsants and antihypertensives (Chan et al. (1997); Gackenheimer et al. (1995); Dempcy et al. (1991)). Also, triazoles associated with various heterocycles are one of the research areas of interesting pharmacological activities, some analogues are used for the treatment of hepatitisC and HIV-1 (De Clercq, (1997); De Clercq, (2002); Alvarez et al. (1994)).

The molecule of the title compound is built up from two fused six-membered rings to a phenyl ring and to a five-membered ring which is connected to butanol group as shown in Fig.1. The fused rings are almost planar, with a maximum deviation of -0.0175 (15) Å and -0.0058 (15) Å for C8 and C1 respectively. The dihedral angle between the quinazoline mean plane and the phenyl ring amount to 7.88 (8)°. The triazol ring is approximately perpendicular to the phenyl ring and to the quinazoline system, with a dihedral angles of 84.38 (10)° and 76.55 (8)° respectively. The stereochemical arrangement of the butanol chain with C18—C19—C20—C21 torsion angles in the range of 178.34 (19) ° corresponds to an anti-periplanar conformation.

An intermolecular O—H···N and O—H···O hydrogen bonds, building an infinite three-dimensional network and ensure the cohesion of the crystal structure as schown in Fig.2 and Table 1.

Experimental

The title compound, 4-(4-((2-phenylquinazolin-4-yloxy)methyl)-1,2,3-triazol -1-yl)butan-1-ol was achieved by cycloaddition of propargylated quinazolinone and azide under microwave conditions with CuI as catalyst and without solvent. The product was obtained with quantitative yield (93%) and short reaction time (Mani Chandrika et al. (2010); Krim et al. (2009)). The crude product was purified passing through a column packed with silica gel. Crystal suitable for X-ray analysis was obtained by slow evaporation of a methanol / methylene chloride (1:4 v/v) solution. The melting point is about 371 - 372 K.