1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-5,6,7,8-tetra­hydro­quinolin-2-yl]thio­urea

Abdullah M Asiri; Hassan M Faidallah; Abdulrahman O Al-Youbi; Khalid A Alamry; Seik Weng Ng

doi:10.1107/S1600536811033046

. 2011 Aug 27;67(Pt 9):o2430. doi: 10.1107/S1600536811033046

1-Benzoyl-3-[3-cyano-8-methyl-4-(1-methyl-1H-pyrrol-2-yl)-5,6,7,8-tetrahydroquinolin-2-yl]thiourea

Abdullah M Asiri ^a,^b, Hassan M Faidallah ^a, Abdulrahman O Al-Youbi ^a, Khalid A Alamry ^a, Seik Weng Ng ^c,^a,^*

PMCID: PMC3200694 PMID: 22064903

Abstract

In the N-substituted benzoylthiourea, C₂₄H₂₃N₅OS, the benzoylthiourea unit is non-planar (r.m.s. deviation = 0.126 Å). The aliphatic part of the tetrahydroquinoline fused-ring system is disordered over two positions in a 0.592 (5):0.408 (5) ratio. The pyridine and pyrrole rings are twisted by 55.2 (1)° in order to avoid crowding of their respective substituents. Pairs of molecules are linked by N—H⋯N hydrogen bonds, forming centrosymmetric dimers. Furthermore, an intramolecular N—H⋯O hydrogen bond stabilizes the molecular conformation.

Related literature

For medicinal properties of cyanopyridines, see: Cocco et al. (2005 ▶); El-Hawash et al. (2006 ▶).

Experimental

Crystal data

C₂₄H₂₃N₅OS
M _r = 429.53
Triclinic,
a = 9.7072 (4) Å
b = 10.4928 (5) Å
c = 11.8828 (5) Å
α = 82.245 (4)°
β = 84.263 (3)°
γ = 63.671 (4)°
V = 1073.76 (8) Å³
Z = 2
Cu Kα radiation
μ = 1.55 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T _min = 0.654, T _max = 0.747
7386 measured reflections
4218 independent reflections
3897 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.146
S = 1.03
4218 reflections
294 parameters
20 restraints
H-atom parameters constrained
Δρ_max = 1.25 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033046/bt5613sup1.cif

e-67-o2430-sup1.cif^{(25.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033046/bt5613Isup2.hkl

e-67-o2430-Isup2.hkl^{(206.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033046/bt5613Isup3.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
N4—H4⋯O1	0.88	1.90	2.594 (2)	135
N5—H5⋯N3ⁱ	0.88	2.22	3.058 (2)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank King Abdulaziz University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

There are several studies on cyanopyridine derivatives as these compounds exhibit useful anticancer and antiviral activities Cocco et al., 2005; El-Hawash et al., 2006). If these compounds possess a primary amine group, then they can be reacted with phenyl isothiocyanate to yield cyanopyridine-benzoythiourea derivatives, yet another class of medicinal compounds. Because of the ease phenyl isothiocyanate reacts with primary amines, we have in this study used 2-amino-3-cyano–8-methyl-4-(N-methylpyrrolyl)-5,6,7,8-tetrahydroquinoline to synthesize the correponding N-substituted benzoylthiourea (Scheme I).

In the N-substituted benzoylthiourea, C₂₄H₂₃N₅OS, the benzoylthiourea portion is somewhat non-planar; the mean plane is aligned at 67.9 (1)° with respect the the mean-plane of the non-planar tetrahydroquinoline fused-ring. An intramolecular N–H···O hydrogen bond appears to prevent further twisting in the benzoylthiourea portion. The aliphatic portion of the tetrahydroquinoline fused-ring is disordered over two positions in a 0.592 (5): 0.408 ratio. The pyridine ring (which has a cyanide substituent) and the pyrrole ring (which has a methyl substitutent) are twisted by 55.2 (1) ° in order to avoid crowding of their respective substituents (Fig. 1). Two molecules are linked by an N–H···O hydrogen bonds to form a centrosymmetric dimer (Table 1).

Experimental

2-Amino-3-cyano–8-methyl-4-(N-methylpyrrolyl)-5,6,7,8-tetrahydroquinoline (10 mmol), potassium carbonate (20 mmol) in dry acetone (25 ml) was stirred and then treated with phenyl isothiocyanate (12 mmol). The mixture was heated for 10 h; the acetone was removed under pressure and the solid mass dissolved in water. The solution was acidified with 2 N hydrochloric acid. The crude product was purified by recrystallization from ethanol.