3-(Adamantan-1-yl)-4-ethyl-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(14)H(21)N(3)S, the 1,2,4-triazole ring is nearly planar, with a maximum deviation of 0.003 (4) Å. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯S hydrogen bonds.

Related literature

For the biological activity of adamantane derivatives, see: Al-Omar et al. (2010 ▶); Al-Deeb et al. (2006 ▶); El-Emam et al. (2004 ▶); Kadi et al. (2007 ▶, 2010 ▶); Vernier et al. (1969 ▶). For the synthesis of the title compound, see: El-Emam & Ibrahim (1991 ▶). For related structures of adamantane derivatives, see: Almutairi et al. (2012 ▶); Al-Tamimi et al. (2010 ▶); Rouchal et al. (2010 ▶); Wang et al. (2011 ▶); Al-Abdullah et al. (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H21N3S

M = 263.40

Monoclinic,

a = 13.8329 (7) Å

b = 7.3107 (4) Å

c = 17.5302 (12) Å

β = 128.157 (4)°

V = 1393.99 (16) Å3

Z = 4

Cu Kα radiation

μ = 1.94 mm−1

T = 296 K

0.58 × 0.12 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.228, T max = 0.906

8009 measured reflections

2448 independent reflections

1632 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.167

S = 1.13

2448 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014407/is5108sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014407/is5108Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014407/is5108Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H21N3S	F(000) = 568
Mr = 263.40	Dx = 1.255 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 592 reflections
a = 13.8329 (7) Å	θ = 4.1–66.5°
b = 7.3107 (4) Å	µ = 1.94 mm−1
c = 17.5302 (12) Å	T = 296 K
β = 128.157 (4)°	Needle, colourless
V = 1393.99 (16) Å3	0.58 × 0.12 × 0.05 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2448 independent reflections
Radiation source: fine-focus sealed tube	1632 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.093
φ and ω scans	θmax = 67.5°, θmin = 4.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.228, Tmax = 0.906	k = −8→6
8009 measured reflections	l = −20→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.0553P)2 + 1.0409P] where P = (Fo2 + 2Fc2)/3
2448 reflections	(Δ/σ)max = 0.001
168 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	−0.10923 (11)	0.88672 (13)	0.05119 (8)	0.0602 (4)
N1	0.0606 (3)	0.6128 (4)	0.1520 (2)	0.0452 (7)
N2	0.0957 (4)	0.7839 (4)	0.0738 (3)	0.0591 (10)
N3	0.1903 (3)	0.6609 (4)	0.1203 (2)	0.0571 (9)
C1	0.0152 (4)	0.7606 (4)	0.0913 (3)	0.0490 (10)
C2	0.1677 (4)	0.5561 (5)	0.1684 (3)	0.0479 (9)
C3	0.2544 (4)	0.4078 (5)	0.2347 (3)	0.0505 (9)
C4	0.3537 (4)	0.3859 (5)	0.2218 (4)	0.0733 (13)
H4A	0.3954	0.5018	0.2345	0.088*
H4B	0.3158	0.3509	0.1554	0.088*
C5	0.4475 (5)	0.2398 (6)	0.2914 (5)	0.0821 (15)
H5A	0.5104	0.2284	0.2822	0.099*
C6	0.5089 (5)	0.2972 (7)	0.3961 (5)	0.0953 (18)
H6A	0.5695	0.2068	0.4406	0.114*
H6B	0.5504	0.4136	0.4096	0.114*
C7	0.4113 (4)	0.3141 (6)	0.4098 (3)	0.0710 (12)
H7A	0.4502	0.3481	0.4771	0.085*
C8	0.3435 (4)	0.1329 (5)	0.3865 (3)	0.0660 (12)
H8A	0.2810	0.1455	0.3951	0.079*
H8B	0.4009	0.0391	0.4307	0.079*
C9	0.2836 (4)	0.0760 (5)	0.2820 (3)	0.0587 (11)
H9A	0.2415	−0.0414	0.2682	0.070*
C10	0.1908 (4)	0.2214 (5)	0.2139 (3)	0.0524 (10)
H10A	0.1279	0.2312	0.2223	0.063*
H10B	0.1512	0.1862	0.1473	0.063*
C11	0.3813 (5)	0.0576 (6)	0.2681 (4)	0.0781 (14)
H11A	0.3433	0.0231	0.2016	0.094*
H11B	0.4397	−0.0369	0.3106	0.094*
C12	0.3189 (4)	0.4605 (5)	0.3421 (3)	0.0595 (11)
H12A	0.3607	0.5768	0.3564	0.071*
H12B	0.2579	0.4739	0.3523	0.071*
C13	−0.0034 (4)	0.5359 (5)	0.1871 (3)	0.0486 (9)
H13A	−0.0375	0.6350	0.2006	0.058*
H13B	0.0553	0.4710	0.2474	0.058*
C14	−0.1058 (4)	0.4064 (5)	0.1148 (3)	0.0577 (10)
H14A	−0.1485	0.3664	0.1389	0.087*
H14B	−0.0717	0.3024	0.1056	0.087*
H14C	−0.1622	0.4682	0.0540	0.087*
H1N2	0.089 (3)	0.868 (5)	0.035 (3)	0.063 (12)*

	U11	U22	U33	U12	U13	U23
S1	0.0812 (8)	0.0444 (6)	0.0664 (7)	0.0174 (5)	0.0513 (6)	0.0157 (4)
N1	0.060 (2)	0.0367 (15)	0.0490 (17)	0.0075 (14)	0.0389 (16)	0.0066 (12)
N2	0.088 (3)	0.0436 (19)	0.069 (2)	0.0136 (17)	0.060 (2)	0.0182 (16)
N3	0.076 (2)	0.0419 (17)	0.074 (2)	0.0115 (16)	0.057 (2)	0.0146 (15)
C1	0.071 (3)	0.0329 (18)	0.048 (2)	0.0057 (17)	0.039 (2)	0.0031 (15)
C2	0.064 (3)	0.0383 (19)	0.053 (2)	0.0010 (17)	0.042 (2)	0.0002 (15)
C3	0.059 (3)	0.040 (2)	0.064 (2)	0.0053 (17)	0.043 (2)	0.0074 (16)
C4	0.086 (3)	0.051 (2)	0.120 (4)	0.012 (2)	0.082 (3)	0.020 (2)
C5	0.074 (3)	0.062 (3)	0.140 (5)	0.022 (2)	0.080 (4)	0.029 (3)
C6	0.061 (3)	0.071 (3)	0.127 (5)	0.005 (3)	0.045 (3)	0.025 (3)
C7	0.055 (3)	0.064 (3)	0.068 (3)	−0.004 (2)	0.025 (2)	0.005 (2)
C8	0.053 (3)	0.057 (3)	0.070 (3)	0.007 (2)	0.029 (2)	0.023 (2)
C9	0.061 (3)	0.037 (2)	0.078 (3)	0.0047 (18)	0.043 (2)	0.0093 (18)
C10	0.062 (3)	0.044 (2)	0.055 (2)	0.0045 (18)	0.038 (2)	0.0048 (16)
C11	0.081 (3)	0.052 (3)	0.118 (4)	0.022 (2)	0.070 (3)	0.020 (3)
C12	0.060 (3)	0.045 (2)	0.063 (3)	−0.0037 (18)	0.032 (2)	0.0001 (18)
C13	0.065 (3)	0.043 (2)	0.052 (2)	0.0083 (18)	0.043 (2)	0.0071 (16)
C14	0.060 (3)	0.049 (2)	0.067 (3)	−0.0003 (19)	0.041 (2)	−0.0006 (18)

S1—C1	1.677 (4)	C7—C12	1.521 (5)
N1—C1	1.367 (4)	C7—C8	1.526 (5)
N1—C2	1.386 (5)	C7—H7A	0.9800
N1—C13	1.468 (4)	C8—C9	1.530 (6)
N2—C1	1.337 (5)	C8—H8A	0.9700
N2—N3	1.366 (4)	C8—H8B	0.9700
N2—H1N2	0.87 (4)	C9—C10	1.520 (5)
N3—C2	1.312 (4)	C9—C11	1.522 (6)
C2—C3	1.497 (5)	C9—H9A	0.9800
C3—C4	1.533 (5)	C10—H10A	0.9700
C3—C10	1.539 (5)	C10—H10B	0.9700
C3—C12	1.553 (5)	C11—H11A	0.9700
C4—C5	1.535 (6)	C11—H11B	0.9700
C4—H4A	0.9700	C12—H12A	0.9700
C4—H4B	0.9700	C12—H12B	0.9700
C5—C11	1.522 (6)	C13—C14	1.514 (5)
C5—C6	1.530 (7)	C13—H13A	0.9700
C5—H5A	0.9800	C13—H13B	0.9700
C6—C7	1.515 (7)	C14—H14A	0.9600
C6—H6A	0.9700	C14—H14B	0.9600
C6—H6B	0.9700	C14—H14C	0.9600
C1—N1—C2	108.5 (3)	C7—C8—C9	110.2 (3)
C1—N1—C13	121.5 (3)	C7—C8—H8A	109.6
C2—N1—C13	130.0 (3)	C9—C8—H8A	109.6
C1—N2—N3	113.9 (3)	C7—C8—H8B	109.6
C1—N2—H1N2	124 (3)	C9—C8—H8B	109.6
N3—N2—H1N2	122 (3)	H8A—C8—H8B	108.1
C2—N3—N2	104.3 (3)	C10—C9—C11	109.8 (3)
N2—C1—N1	103.4 (3)	C10—C9—C8	108.7 (3)
N2—C1—S1	128.2 (3)	C11—C9—C8	109.8 (4)
N1—C1—S1	128.3 (3)	C10—C9—H9A	109.5
N3—C2—N1	109.9 (3)	C11—C9—H9A	109.5
N3—C2—C3	121.8 (3)	C8—C9—H9A	109.5
N1—C2—C3	128.2 (3)	C9—C10—C3	110.6 (3)
C2—C3—C4	108.8 (3)	C9—C10—H10A	109.5
C2—C3—C10	113.0 (3)	C3—C10—H10A	109.5
C4—C3—C10	107.9 (3)	C9—C10—H10B	109.5
C2—C3—C12	110.2 (3)	C3—C10—H10B	109.5
C4—C3—C12	108.0 (3)	H10A—C10—H10B	108.1
C10—C3—C12	108.8 (3)	C9—C11—C5	109.0 (3)
C3—C4—C5	110.5 (3)	C9—C11—H11A	109.9
C3—C4—H4A	109.6	C5—C11—H11A	109.9
C5—C4—H4A	109.6	C9—C11—H11B	109.9
C3—C4—H4B	109.6	C5—C11—H11B	109.9
C5—C4—H4B	109.6	H11A—C11—H11B	108.3
H4A—C4—H4B	108.1	C7—C12—C3	110.3 (3)
C11—C5—C6	111.0 (4)	C7—C12—H12A	109.6
C11—C5—C4	108.8 (4)	C3—C12—H12A	109.6
C6—C5—C4	109.4 (4)	C7—C12—H12B	109.6
C11—C5—H5A	109.2	C3—C12—H12B	109.6
C6—C5—H5A	109.2	H12A—C12—H12B	108.1
C4—C5—H5A	109.2	N1—C13—C14	112.5 (3)
C7—C6—C5	108.9 (4)	N1—C13—H13A	109.1
C7—C6—H6A	109.9	C14—C13—H13A	109.1
C5—C6—H6A	109.9	N1—C13—H13B	109.1
C7—C6—H6B	109.9	C14—C13—H13B	109.1
C5—C6—H6B	109.9	H13A—C13—H13B	107.8
H6A—C6—H6B	108.3	C13—C14—H14A	109.5
C6—C7—C12	109.6 (4)	C13—C14—H14B	109.5
C6—C7—C8	110.4 (4)	H14A—C14—H14B	109.5
C12—C7—C8	108.7 (3)	C13—C14—H14C	109.5
C6—C7—H7A	109.4	H14A—C14—H14C	109.5
C12—C7—H7A	109.4	H14B—C14—H14C	109.5
C8—C7—H7A	109.4
C1—N2—N3—C2	0.3 (4)	C11—C5—C6—C7	−59.4 (5)
N3—N2—C1—N1	−0.6 (4)	C4—C5—C6—C7	60.7 (5)
N3—N2—C1—S1	177.7 (3)	C5—C6—C7—C12	−61.3 (5)
C2—N1—C1—N2	0.6 (4)	C5—C6—C7—C8	58.3 (5)
C13—N1—C1—N2	−178.0 (3)	C6—C7—C8—C9	−58.9 (5)
C2—N1—C1—S1	−177.7 (3)	C12—C7—C8—C9	61.4 (5)
C13—N1—C1—S1	3.8 (5)	C7—C8—C9—C10	−61.4 (4)
N2—N3—C2—N1	0.1 (4)	C7—C8—C9—C11	58.8 (4)
N2—N3—C2—C3	−176.4 (3)	C11—C9—C10—C3	−60.1 (4)
C1—N1—C2—N3	−0.4 (4)	C8—C9—C10—C3	60.0 (4)
C13—N1—C2—N3	177.9 (3)	C2—C3—C10—C9	178.9 (3)
C1—N1—C2—C3	175.8 (3)	C4—C3—C10—C9	58.6 (4)
C13—N1—C2—C3	−5.9 (6)	C12—C3—C10—C9	−58.3 (4)
N3—C2—C3—C4	−8.8 (5)	C10—C9—C11—C5	60.7 (5)
N1—C2—C3—C4	175.4 (4)	C8—C9—C11—C5	−58.8 (5)
N3—C2—C3—C10	−128.6 (4)	C6—C5—C11—C9	59.8 (5)
N1—C2—C3—C10	55.6 (5)	C4—C5—C11—C9	−60.7 (5)
N3—C2—C3—C12	109.5 (4)	C6—C7—C12—C3	61.0 (5)
N1—C2—C3—C12	−66.3 (5)	C8—C7—C12—C3	−59.7 (5)
C2—C3—C4—C5	177.9 (4)	C2—C3—C12—C7	−177.4 (3)
C10—C3—C4—C5	−59.2 (5)	C4—C3—C12—C7	−58.7 (4)
C12—C3—C4—C5	58.2 (5)	C10—C3—C12—C7	58.2 (4)
C3—C4—C5—C11	61.2 (5)	C1—N1—C13—C14	82.7 (4)
C3—C4—C5—C6	−60.3 (5)	C2—N1—C13—C14	−95.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1i	0.88 (4)	2.47 (4)	3.338 (4)	170 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1i	0.88 (4)	2.47 (4)	3.338 (4)	170 (4)

Symmetry code: (i) .