4-Hy­droxy-6-(4-meth­oxy­phen­yl)-4-phenyl-1,3-diazinane-2-thione

H C Devarajegowda; K R Roopashree; Irfan Ali Mohammed; Mahalakshmi; Ravish Sankolli

doi:10.1107/S1600536811008002

. 2011 Mar 9;67(Pt 4):o815. doi: 10.1107/S1600536811008002

4-Hydroxy-6-(4-methoxyphenyl)-4-phenyl-1,3-diazinane-2-thione

H C Devarajegowda ^a,^*, K R Roopashree ^a, Irfan Ali Mohammed ^b, Mahalakshmi ^a, Ravish Sankolli ^c

PMCID: PMC3099814 PMID: 21754101

Abstract

In the title compound, C₁₇H₁₈N₂O₂S, the 1,3-diazinane-2-thione ring system is not coplanar with the benzene ring and methoxyphenyl ring system, the dihedral angle between the planes being 65.58 (13) and 89.18 (10)°, respectively. The crystal structure is characterized by intermolecular O—H⋯S, N—H⋯S, N—H⋯O and C—H⋯S hydrogen bonding.

Related literature

For general background to pyrimidines, see: Cheng (1969 ▶); Scott et al. (1959 ▶); Jonak et al. (1972 ▶); Falco et al. (1961 ▶); Ram (1990 ▶); Howells et al. (1981 ▶); Pershin et al. (1972 ▶); Matolcsy (1971 ▶); Prikazchikova et al. (1975 ▶). For the synthesis, see: Paghdar et al. (2007 ▶). For a related structure, see: Yamin et al. (2005 ▶).

Experimental

Crystal data

C₁₇H₁₈N₂O₂S
M _r = 314.39
Monoclinic,
a = 12.6016 (3) Å
b = 6.3375 (1) Å
c = 20.6637 (4) Å
β = 97.890 (2)°
V = 1634.64 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.18 × 0.16 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 ▶) T _min = 0.963, T _max = 1.000
18135 measured reflections
3547 independent reflections
2566 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.115
S = 1.08
3547 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008002/bv2177sup1.cif

e-67-0o815-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008002/bv2177Isup2.hkl

e-67-0o815-Isup2.hkl^{(170.4KB, hkl)}

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
O2—H2⋯S1ⁱ	0.88 (3)	2.51 (3)	3.3688 (18)	169 (2)
C14—H14⋯S1ⁱ	1.030 (19)	2.695 (18)	3.666 (2)	157.0 (14)
N4—H4⋯S1ⁱⁱ	0.86	2.47	3.2990 (19)	163
N5—H5⋯O3ⁱⁱⁱ	0.86	2.18	3.032 (2)	169
C20—H20⋯S1^iv	0.93	2.86	3.772 (2)	166

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

Acknowledgments

The authors thank Professor T. N. Guru Row and Mr Venkatesha R. Hathwar, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help with the data collection.

supplementary crystallographic information

Comment

Pyrimidines, being an integral part of DNA and RNA, exhibit diverse pharmacological properties as effective bactericide, fungicide, viricide, insecticide, and medicinal agents (Cheng, 1969; Scott et al., 1959). Certain pyrimidines and annulated pyrimidine derivatives are also known to display anticancer, antimalarial, antileishmanial and antifilarial activities (Jonak et al., 1972; Falco et al. 1961; Ram, 1990; Howells et al., 1981). Pyrimidines and thio-pyrimidines play an essential role in several biological processes and have a considerable chemical and pharmacological importance. In particular, the pyrimidine nucleus can be found in a broad variety of antibacterial and antitumor agents as well as in agrochemical and veterinary products (Pershin et al., 1972; Matolcsy, 1971; Prikazchikova et al., 1975).

The asymmetric unit of the 4-hydroxy-6-(4-methoxyphenyl)-4-phenyl tetrahydropyrimidine-2(1H)-thione contains one molecule (Fig. 1). The thio-tetrahydropyrimidine ring system is not coplanar with the benzene ring and methoxyphenyl ring system; the dihedral angle between the two planes 65.58 (13)° and 89.18 (10)° respectively. The crystal structure shows intermolecular O2—H2···S1, N4—H4···S1, N5—H5···O3, C14—H14···S1 & C20—H20···S1 and C6—H6···S1 intramolecular hydrogen bonds. Bond distances and bond angles within the aromatic rings are in agreement with those observed in a related structure (Yamin et al., 2005).

Experimental

A general procedure for the synthesis of 4-hydroxy-6-(4-methoxyphenyl)- 4-phenyl-3,4-dihydropyrimidine-2(1H)-thione is given in Paghdar et al., 2007. An equimolar mixture of (2E)-1,3-diphenylprop-2-en-1-one and thiourea (0.01 mol) were dissolved in minimum amount of ethanol. Potassium hydroxide solution (2.5 ml) was added slowly and the mixture stirred for 10 h until the entire mixture becomes very cloudy. Then the mixture was neutralized with 10% HCl and poured slowly into 100 ml of cold water with constant stirring. The precipitate obtained was filtered, washed and recrystallized from ethanol.