1-(4,6-Dimethyl­pyrimidin-2-yl)-3-(3,5-dinitro­benzo­yl)thio­urea monohydrate

Sohail Saeed; Naghmana Rashid; Wing-Tak Wong; Rizwan Hussain

doi:10.1107/S1600536811012323

. 2011 Apr 13;67(Pt 5):o1094. doi: 10.1107/S1600536811012323

1-(4,6-Dimethylpyrimidin-2-yl)-3-(3,5-dinitrobenzoyl)thiourea monohydrate

Sohail Saeed ^a,^*, Naghmana Rashid ^a, Wing-Tak Wong ^b, Rizwan Hussain ^c

PMCID: PMC3089191 PMID: 21754414

Abstract

The organic molecule in the title molecule, C₁₄H₁₂N₆O₅S·H₂O, is roughly planar with a maximum deviation of 0.156 (2) Å. An intramolecular N—H⋯N hydrogen bond occurs. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen-bonding interactions connect the molecules into a two-dimensional network that lies parallel to (101).

Related literature

For background to this study and our previous work on the structural chemistry of N,N′-disubstituted thiourea, see: Saeed et al. (2011 ▶).

Experimental

Crystal data

C₁₄H₁₂N₆O₅S·H₂O
M _r = 394.37
Monoclinic,
a = 6.7892 (6) Å
b = 10.1823 (9) Å
c = 24.267 (2) Å
β = 92.901 (1)°
V = 1675.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 297 K
0.40 × 0.16 × 0.14 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.909, T _max = 0.967
9067 measured reflections
2942 independent reflections
2499 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.105
S = 1.06
2942 reflections
263 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012323/pv2402sup1.cif

e-67-o1094-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012323/pv2402Isup2.hkl

e-67-o1094-Isup2.hkl^{(144.4KB, 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
N4—H4N⋯O6	0.88 (2)	1.97 (2)	2.849 (2)	171.9 (19)
N3—H3N⋯N6	0.83 (2)	2.00 (2)	2.705 (2)	141.8 (19)
O6—H6A⋯O3ⁱ	0.82 (4)	2.32 (4)	3.119 (3)	168 (4)
O6—H6B⋯O2ⁱⁱ	0.73 (4)	2.44 (4)	3.143 (3)	164 (4)
O6—H6B⋯O1ⁱⁱ	0.73 (4)	2.62 (4)	3.248 (3)	146 (4)

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

Acknowledgments

The authors are grateful to Allama Iqbal Open University, Islamabad, Pakistan, for the allocation of research and analytical laboratory facilities.

supplementary crystallographic information

Comment

The background to this study has been described in our previous work on the structural chemistry of N,N'-disubstituted thiourea (Saeed et al., 2011). In continuation of our studies, the crystal structure of the title compound, is presented in this paper.

In the title molecule (Fig. 1), the nitro groups N1/O1/O2 and N2/O3/O4 are oriented are 5.05 (11) and 9.40 (15)°, respectively, with rest to the mean-plane of the phenyl ring C1—C6. Moreover, the 4,6-dimethyl-pyrimidinyl ring plane, C9—C14/N5/N6, makes a dihedral angle of 1.31 (5)° with the the plane formed by the atoms C7/O5/N3/C8/S1/N4.

The structure is stabilized by intra-molecular N—H···O and N—H···N hydrogen bonding interactions. The inter-molecular hydrogen bonds O—H···O link the molecules into a two dimensinal network (Tab. 1 and Fig. 2).

Experimental

A solution of 3,5-dinitrobenzoyl chloride (0.01 mol) in anhydrous acetone (75 ml) and 3% tetrabutylammonium bromide as a phase-transfer catalyst in anhydrous acetone was added dropwise to a suspension of dry potassium thiocyanate (0.01 mol) in acetone (50 ml) and the reaction mixture was refluxed for 50 min. After cooling to room temperature, a solution of 2-amino-4,6-dimethylpyrimidine (0.01 mol) in anhydrous acetone (25 ml) was added dropwise and the resulting mixture refluxed for 3 h. Hydrochloric acid (0.1 N, 300 ml) was added, and the solution was filtered. The solid product was washed with water and purified by re-crystallization from ethanol.