3-[2-Hy­droxy-3-(2,4,6-trimethyl­phen­yl)prop­yl]-3-methyl-1-phenyl­thio­urea

Abel M Maharramov; Ali N Khalilov; Nurlana D Sadikhova; Atash V Gurbanov; Seik Weng Ng

doi:10.1107/S1600536811012736

. 2011 Apr 13;67(Pt 5):o1087. doi: 10.1107/S1600536811012736

3-[2-Hydroxy-3-(2,4,6-trimethylphenyl)propyl]-3-methyl-1-phenylthiourea

Abel M Maharramov ^a, Ali N Khalilov ^a, Nurlana D Sadikhova ^a, Atash V Gurbanov ^a, Seik Weng Ng ^b,^*

PMCID: PMC3089238 PMID: 21754408

Abstract

In the title compound, C₂₀H₂₆N₂OS, four non-H atoms of the thiourea unit are approximately planar (r.m.s. deviation = 0.005 Å); the phenyl and benzene rings are twisted out of this plane by 28.55 (7) and 60.00 (7)°, respectively. An intramolecular N—H⋯O hydrogen bond occurs. The hydroxy group is hydrogen bonded to the double-bond S atom of an inversion-related molecule, generating a hydrogen-bonded dimer in the crystal structure.

Related literature

The title compund was prepared by a reaction of 1-methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol and phenyl isothiocyanate; for the structure of the reactant 1-methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol, see: Maharramov et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₂₆N₂OS
M _r = 342.49
Monoclinic,
a = 14.6313 (11) Å
b = 8.1579 (6) Å
c = 16.4455 (12) Å
β = 109.040 (1)°
V = 1855.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.947, T _max = 0.964
10052 measured reflections
4160 independent reflections
3542 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.112
S = 1.04
4160 reflections
229 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.24 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012736/xu5185sup1.cif

e-67-o1087-sup1.cif^{(19.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012736/xu5185Isup2.hkl

e-67-o1087-Isup2.hkl^{(203.9KB, 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
O1—H1⋯S1ⁱ	0.83 (1)	2.50 (1)	3.219 (1)	146 (2)
N2—H2⋯O1	0.88 (1)	1.89 (1)	2.739 (2)	165 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank Baku State University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

We have recently reported the synthesis and crystal structure of 1-methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol (Maharramov et al., 2011). This secondary amine behaves like a conventional secondary amine in its reaction with phenyl isothiocyanate to furnish a thiourea (Scheme I). The four-atoms N–C(═S)–N unit of C₂₀H₂₆N₂OS is planar [r.m.s. deviation 0.005 Å]; the phenyl ring connected to one of the two flanking N atoms is twisted out of this plane 28.6 (1)° (Fig. 1). The propyl chain connected to the other N atom bears a hydroxy substituent; this serves as hydrogen-bond donor acceptor to the double-bond S atom of an inversion-related molecule to generate a hydrogen-bonded dimer.

Experimental

1-Methylamino-3-(2,4,6-trimethylphenyl)propan-2-ol was synthesized as reported (Maharramov et al., 2011). The compound (10 mmol) and phenyl isothiocyanate (10 mmol) were heated in benzene (50 mol) for 10 h. The solvent was removed and the product recrystallized from ethanol to yield colorless crystals, m.p. 413–414 K; yield 90%.