1-(Adamantan-1-ylcarbon­yl)-3-(2,6-difluoro-4-hy­droxy­phen­yl)thio­urea

Shaaban K Mohamed; Abdel-Aal M Jaber; Sohail Saeed; Khuram Shahzad Ahmad; Wing-Tak Wong

doi:10.1107/S1600536812018806

. 2012 May 2;68(Pt 6):o1597. doi: 10.1107/S1600536812018806

1-(Adamantan-1-ylcarbonyl)-3-(2,6-difluoro-4-hydroxyphenyl)thiourea

Shaaban K Mohamed ^a, Abdel-Aal M Jaber ^b, Sohail Saeed ^c,^*, Khuram Shahzad Ahmad ^c, Wing-Tak Wong ^d

PMCID: PMC3379207 PMID: 22719405

Abstract

In the title molecule, C₁₈H₂₀F₂N₂O₂S, the 2,6-difluoro-4-hydroxyphenyl ring and the carbonylthiourea group are each essentially planar, with maximum deviations of atoms from their mean planes of 0.0113 (14) and 0.1017 (15) Å, respectively; the dihedral angle between these two planes is 71.03 (6)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, N—H⋯O and O—H⋯S hydrogen bonds connect the molecules into chains running diagonally across the bc plane. C—H⋯S and C—H⋯F contacts are also observed.

Related literature

For background studies of thiourea derivatives, see: Saeed et al. (2011 ▶). For a related structure, see: Saeed et al. (2010 ▶).

Experimental

Crystal data

C₁₈H₂₀F₂N₂O₂S
M _r = 366.42
Triclinic,
a = 7.3985 (9) Å
b = 10.4953 (13) Å
c = 12.4094 (15) Å
α = 65.554 (2)°
β = 79.372 (2)°
γ = 89.766 (2)°
V = 859.34 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.38 × 0.36 × 0.08 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.920, T _max = 0.982
4824 measured reflections
2976 independent reflections
2399 reflections with I > 2σ(I)
R _int = 0.010

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.100
S = 1.04
2976 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812018806/pv2537sup1.cif

e-68-o1597-sup1.cif^{(25.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018806/pv2537Isup2.hkl

e-68-o1597-Isup2.hkl^{(146.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018806/pv2537Isup3.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
N1—H1⋯O2	0.79 (2)	2.09 (2)	2.692 (2)	133 (2)
N1—H1⋯O2ⁱ	0.79 (2)	2.52 (2)	3.185 (3)	142 (2)
O1—H1O⋯S1ⁱⁱ	0.87 (3)	2.36 (3)	3.212 (2)	169 (3)
C14—H14A⋯S1ⁱⁱⁱ	0.97	2.84	3.761 (2)	159
C14—H14B⋯F1^iv	0.97	2.45	3.354 (3)	155

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

Acknowledgments

SS is thankful to the University of Hong Kong for providing the facility for crystallographic studies.

supplementary crystallographic information

Comment

In continuation of our studies on structural chemistry of N,N'-disubstituted thiourea (Saeed, et al., 2011), the structure of the title compound is described in this article.

In the title molecule (Fig. 1), the 2,6-difluoro-4-hydroxy-phenyl ring (C1–C6/O1/F1/F2) and the carbonyl thiourea group (S1/N1/N2/O2/C7/C8) are individually more or less planar, with maximum deviations of atoms from their mean planes being 0.0113 (14) Å for O1 and 0.1017 (15) Å for N2, respectively; the dihedral angle between these two planes is 71.03 (6)°.

Hydrogen bonding interactions were observed in the crystal lattice which connect the molecules into 1-D chains running diagonally across the b-c-plane (Table 1 and Fig. 2).

Experimental

A mixture of adamantane-1-carbonyl chloride (199 mg, 1 mmol), 4-amino-3,5-difluorophenol (145 mg, 1 mmol) and potassium thiocyanate (100 mg) was heated for 30 minutes in ethanol (5 ml) at 351 K. The reaction mixture was left overnight to cool down at room temperature to afford a solid product which was filtered off, washed and recrystallized from ethanol. Colorless crystals suitable for X-ray crystallographic studies were collected and dried (yield = 82%; m. p. = 455-456 K).