2-{[5-(Adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfan-yl}-N,N-dimethyl-ethanamine.

In the title compound, C(17)H(28)N(4)S, the 1,2,4-triazole ring is nearly planar [maximum deviation = 0.005 (2) Å]. There are no significant hydrogen bonds observed in the crystal structure. The crystal studied was a non-merohedral twin, the refined ratio of twin components being 0.281 (3):0.719 (3).

Related literature

For the biological activity of adamantyl 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 structures of related adamantyl-1,2,4-triazoles, see: Almutairi et al. (2012 ▶); Al-Tamimi et al. (2010 ▶); Al-Abdullah et al. (2012 ▶). For the structures of substituted sulfanyl-1,2,4-triazoles, see: Fun et al. (2011 ▶); Wang et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H28N4S

M = 320.49

Monoclinic,

a = 12.5133 (7) Å

b = 10.3779 (5) Å

c = 14.3044 (8) Å

β = 106.766 (3)°

V = 1778.63 (16) Å3

Z = 4

Cu Kα radiation

μ = 1.62 mm−1

T = 296 K

0.64 × 0.59 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.204, T max = 0.923

3267 measured reflections

3267 independent reflections

2846 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.184

S = 1.13

3267 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.37 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/S160053681201464X/rz2734sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201464X/rz2734Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201464X/rz2734Isup3.cml

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

C17H28N4S	F(000) = 696
Mr = 320.49	Dx = 1.197 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3932 reflections
a = 12.5133 (7) Å	θ = 7.7–69.2°
b = 10.3779 (5) Å	µ = 1.62 mm−1
c = 14.3044 (8) Å	T = 296 K
β = 106.766 (3)°	Plate, colourless
V = 1778.63 (16) Å3	0.64 × 0.59 × 0.05 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3267 independent reflections
Radiation source: fine-focus sealed tube	2846 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 69.8°, θmin = 7.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→14
Tmin = 0.204, Tmax = 0.923	k = −12→12
3267 measured reflections	l = 0→16

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.P)2 + 1.1111P] where P = (Fo2 + 2Fc2)/3
3267 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.37 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	0.59451 (7)	0.30472 (8)	0.05471 (7)	0.0589 (3)
N1	0.4306 (2)	0.2967 (2)	0.14471 (19)	0.0478 (6)
N4	0.7649 (3)	0.2967 (3)	−0.0644 (2)	0.0630 (7)
C9	0.2838 (2)	0.2248 (3)	0.2293 (2)	0.0476 (7)
C10	0.3344 (3)	0.2856 (4)	0.3307 (3)	0.0672 (9)
H10A	0.3944	0.2315	0.3689	0.081*
H10B	0.3653	0.3694	0.3234	0.081*
C6	0.2449 (4)	0.3001 (5)	0.3838 (3)	0.0814 (12)
H6A	0.2779	0.3402	0.4477	0.098*
C5	0.1995 (4)	0.1692 (5)	0.3976 (3)	0.0893 (14)
H5A	0.1441	0.1778	0.4328	0.107*
H5B	0.2594	0.1149	0.4359	0.107*
C4	0.1465 (4)	0.1071 (4)	0.2985 (3)	0.0765 (11)
H4A	0.1169	0.0222	0.3077	0.092*
C3	0.0526 (3)	0.1919 (5)	0.2391 (3)	0.0817 (13)
H3A	0.0183	0.1524	0.1761	0.098*
H3B	−0.0041	0.2011	0.2728	0.098*
C13	0.6508 (4)	0.1620 (4)	0.0134 (4)	0.0803 (12)
H13A	0.6560	0.0927	0.0600	0.096*
H13B	0.6015	0.1344	−0.0490	0.096*
C2	0.0985 (3)	0.3229 (4)	0.2249 (3)	0.0757 (11)
H2A	0.0375	0.3775	0.1869	0.091*
C7	0.1513 (4)	0.3853 (5)	0.3230 (4)	0.0861 (13)
H7A	0.0954	0.3977	0.3571	0.103*
H7B	0.1810	0.4691	0.3136	0.103*
C1	0.1858 (3)	0.3084 (4)	0.1699 (3)	0.0653 (9)
H1A	0.2132	0.3927	0.1586	0.078*
H1B	0.1520	0.2684	0.1069	0.078*
C8	0.2350 (3)	0.0923 (3)	0.2444 (3)	0.0666 (9)
H8A	0.2018	0.0521	0.1814	0.080*
H8B	0.2944	0.0367	0.2817	0.080*
C11	0.3702 (2)	0.2040 (3)	0.1772 (2)	0.0477 (7)
N2	0.4021 (2)	0.0897 (2)	0.1572 (2)	0.0577 (7)
N3	0.4859 (3)	0.1046 (3)	0.1120 (2)	0.0599 (7)
C12	0.5001 (3)	0.2289 (3)	0.1054 (2)	0.0516 (7)
C14	0.7641 (4)	0.1909 (5)	0.0031 (4)	0.0874 (14)
H14A	0.8139	0.2124	0.0669	0.105*
H14B	0.7930	0.1140	−0.0196	0.105*
C16	0.7117 (7)	0.2636 (6)	−0.1633 (5)	0.126 (2)
H16A	0.7180	0.3341	−0.2048	0.189*
H16B	0.6342	0.2457	−0.1713	0.189*
H16C	0.7468	0.1886	−0.1805	0.189*
C17	0.4269 (3)	0.4366 (3)	0.1495 (3)	0.0633 (9)
H17A	0.4899	0.4723	0.1330	0.095*
H17B	0.4292	0.4626	0.2145	0.095*
H17C	0.3593	0.4674	0.1043	0.095*
C15	0.8793 (5)	0.3349 (7)	−0.0500 (6)	0.120 (2)
H15A	0.8822	0.4023	−0.0951	0.181*
H15B	0.9217	0.2623	−0.0608	0.181*
H15C	0.9101	0.3655	0.0156	0.181*

	U11	U22	U33	U12	U13	U23
S1	0.0605 (5)	0.0553 (5)	0.0668 (6)	−0.0051 (3)	0.0278 (4)	−0.0023 (4)
N1	0.0524 (14)	0.0418 (13)	0.0497 (15)	0.0000 (10)	0.0156 (11)	0.0003 (10)
N4	0.0598 (17)	0.0665 (18)	0.0661 (19)	0.0050 (13)	0.0236 (14)	0.0030 (14)
C9	0.0478 (15)	0.0505 (16)	0.0430 (16)	0.0012 (12)	0.0105 (13)	−0.0010 (12)
C10	0.060 (2)	0.084 (2)	0.051 (2)	−0.0009 (18)	0.0042 (16)	−0.0097 (17)
C6	0.076 (3)	0.113 (4)	0.054 (2)	−0.003 (2)	0.0162 (19)	−0.021 (2)
C5	0.082 (3)	0.133 (4)	0.059 (3)	0.012 (3)	0.031 (2)	0.017 (2)
C4	0.079 (3)	0.078 (3)	0.083 (3)	−0.011 (2)	0.039 (2)	0.003 (2)
C3	0.056 (2)	0.123 (4)	0.070 (3)	−0.011 (2)	0.0232 (19)	−0.009 (2)
C13	0.081 (3)	0.064 (2)	0.114 (4)	0.0078 (19)	0.056 (3)	0.006 (2)
C2	0.057 (2)	0.095 (3)	0.073 (3)	0.0195 (19)	0.0154 (18)	0.007 (2)
C7	0.085 (3)	0.092 (3)	0.091 (3)	0.009 (2)	0.042 (3)	−0.018 (2)
C1	0.059 (2)	0.080 (2)	0.055 (2)	0.0125 (16)	0.0139 (16)	0.0096 (17)
C8	0.070 (2)	0.063 (2)	0.072 (2)	−0.0051 (16)	0.0289 (18)	0.0026 (17)
C11	0.0505 (16)	0.0440 (15)	0.0476 (17)	0.0002 (12)	0.0126 (13)	0.0023 (12)
N2	0.0657 (16)	0.0454 (14)	0.0686 (18)	0.0029 (12)	0.0299 (14)	0.0032 (12)
N3	0.0682 (17)	0.0466 (15)	0.0727 (19)	0.0041 (12)	0.0327 (15)	0.0027 (12)
C12	0.0531 (17)	0.0499 (17)	0.0499 (18)	0.0020 (13)	0.0118 (14)	0.0008 (13)
C14	0.080 (3)	0.094 (3)	0.096 (3)	0.024 (2)	0.038 (3)	0.024 (3)
C16	0.181 (6)	0.097 (4)	0.082 (4)	0.030 (4)	0.008 (4)	−0.013 (3)
C17	0.069 (2)	0.0442 (17)	0.080 (2)	−0.0017 (15)	0.0273 (18)	−0.0028 (15)
C15	0.082 (3)	0.137 (5)	0.151 (6)	0.003 (3)	0.047 (4)	0.032 (4)

S1—C12	1.742 (3)	C13—C14	1.498 (6)
S1—C13	1.811 (4)	C13—H13A	0.9700
N1—C12	1.361 (4)	C13—H13B	0.9700
N1—C11	1.384 (4)	C2—C7	1.513 (7)
N1—C17	1.455 (4)	C2—C1	1.527 (5)
N4—C16	1.421 (7)	C2—H2A	0.9800
N4—C15	1.441 (6)	C7—H7A	0.9700
N4—C14	1.464 (5)	C7—H7B	0.9700
C9—C11	1.495 (4)	C1—H1A	0.9700
C9—C10	1.539 (5)	C1—H1B	0.9700
C9—C1	1.542 (4)	C8—H8A	0.9700
C9—C8	1.546 (5)	C8—H8B	0.9700
C10—C6	1.531 (6)	C11—N2	1.310 (4)
C10—H10A	0.9700	N2—N3	1.390 (4)
C10—H10B	0.9700	N3—C12	1.309 (4)
C6—C5	1.508 (7)	C14—H14A	0.9700
C6—C7	1.524 (7)	C14—H14B	0.9700
C6—H6A	0.9800	C16—H16A	0.9600
C5—C4	1.524 (7)	C16—H16B	0.9600
C5—H5A	0.9700	C16—H16C	0.9600
C5—H5B	0.9700	C17—H17A	0.9600
C4—C3	1.517 (7)	C17—H17B	0.9600
C4—C8	1.531 (5)	C17—H17C	0.9600
C4—H4A	0.9800	C15—H15A	0.9600
C3—C2	1.513 (7)	C15—H15B	0.9600
C3—H3A	0.9700	C15—H15C	0.9600
C3—H3B	0.9700
C12—S1—C13	98.05 (17)	C7—C2—H2A	109.2
C12—N1—C11	104.8 (2)	C1—C2—H2A	109.2
C12—N1—C17	124.6 (3)	C2—C7—C6	109.8 (4)
C11—N1—C17	130.5 (3)	C2—C7—H7A	109.7
C16—N4—C15	111.7 (5)	C6—C7—H7A	109.7
C16—N4—C14	112.6 (4)	C2—C7—H7B	109.7
C15—N4—C14	107.9 (4)	C6—C7—H7B	109.7
C11—C9—C10	111.7 (3)	H7A—C7—H7B	108.2
C11—C9—C1	112.4 (3)	C2—C1—C9	110.2 (3)
C10—C9—C1	109.5 (3)	C2—C1—H1A	109.6
C11—C9—C8	108.2 (3)	C9—C1—H1A	109.6
C10—C9—C8	107.7 (3)	C2—C1—H1B	109.6
C1—C9—C8	107.1 (3)	C9—C1—H1B	109.6
C6—C10—C9	110.3 (3)	H1A—C1—H1B	108.1
C6—C10—H10A	109.6	C4—C8—C9	110.7 (3)
C9—C10—H10A	109.6	C4—C8—H8A	109.5
C6—C10—H10B	109.6	C9—C8—H8A	109.5
C9—C10—H10B	109.6	C4—C8—H8B	109.5
H10A—C10—H10B	108.1	C9—C8—H8B	109.5
C5—C6—C7	109.9 (4)	H8A—C8—H8B	108.1
C5—C6—C10	109.5 (4)	N2—C11—N1	109.0 (3)
C7—C6—C10	109.0 (4)	N2—C11—C9	123.3 (3)
C5—C6—H6A	109.5	N1—C11—C9	127.6 (3)
C7—C6—H6A	109.5	C11—N2—N3	108.6 (3)
C10—C6—H6A	109.5	C12—N3—N2	106.3 (3)
C6—C5—C4	109.8 (3)	N3—C12—N1	111.2 (3)
C6—C5—H5A	109.7	N3—C12—S1	126.8 (3)
C4—C5—H5A	109.7	N1—C12—S1	122.0 (2)
C6—C5—H5B	109.7	N4—C14—C13	113.7 (4)
C4—C5—H5B	109.7	N4—C14—H14A	108.8
H5A—C5—H5B	108.2	C13—C14—H14A	108.8
C3—C4—C5	109.5 (4)	N4—C14—H14B	108.8
C3—C4—C8	109.4 (4)	C13—C14—H14B	108.8
C5—C4—C8	109.2 (4)	H14A—C14—H14B	107.7
C3—C4—H4A	109.6	N4—C16—H16A	109.5
C5—C4—H4A	109.6	N4—C16—H16B	109.5
C8—C4—H4A	109.6	H16A—C16—H16B	109.5
C2—C3—C4	109.5 (3)	N4—C16—H16C	109.5
C2—C3—H3A	109.8	H16A—C16—H16C	109.5
C4—C3—H3A	109.8	H16B—C16—H16C	109.5
C2—C3—H3B	109.8	N1—C17—H17A	109.5
C4—C3—H3B	109.8	N1—C17—H17B	109.5
H3A—C3—H3B	108.2	H17A—C17—H17B	109.5
C14—C13—S1	109.7 (3)	N1—C17—H17C	109.5
C14—C13—H13A	109.7	H17A—C17—H17C	109.5
S1—C13—H13A	109.7	H17B—C17—H17C	109.5
C14—C13—H13B	109.7	N4—C15—H15A	109.5
S1—C13—H13B	109.7	N4—C15—H15B	109.5
H13A—C13—H13B	108.2	H15A—C15—H15B	109.5
C3—C2—C7	110.0 (4)	N4—C15—H15C	109.5
C3—C2—C1	109.7 (4)	H15A—C15—H15C	109.5
C7—C2—C1	109.6 (3)	H15B—C15—H15C	109.5
C3—C2—H2A	109.2
C11—C9—C10—C6	−177.5 (3)	C10—C9—C8—C4	58.6 (4)
C1—C9—C10—C6	57.3 (4)	C1—C9—C8—C4	−59.2 (4)
C8—C9—C10—C6	−58.8 (4)	C12—N1—C11—N2	−0.5 (4)
C9—C10—C6—C5	60.9 (4)	C17—N1—C11—N2	−179.8 (3)
C9—C10—C6—C7	−59.3 (5)	C12—N1—C11—C9	178.0 (3)
C7—C6—C5—C4	58.9 (5)	C17—N1—C11—C9	−1.3 (5)
C10—C6—C5—C4	−60.8 (5)	C10—C9—C11—N2	113.2 (4)
C6—C5—C4—C3	−59.6 (5)	C1—C9—C11—N2	−123.3 (4)
C6—C5—C4—C8	60.2 (5)	C8—C9—C11—N2	−5.3 (4)
C5—C4—C3—C2	59.8 (5)	C10—C9—C11—N1	−65.1 (4)
C8—C4—C3—C2	−59.8 (5)	C1—C9—C11—N1	58.4 (4)
C12—S1—C13—C14	−157.1 (3)	C8—C9—C11—N1	176.4 (3)
C4—C3—C2—C7	−59.9 (5)	N1—C11—N2—N3	0.8 (4)
C4—C3—C2—C1	60.7 (4)	C9—C11—N2—N3	−177.8 (3)
C3—C2—C7—C6	59.1 (5)	C11—N2—N3—C12	−0.8 (4)
C1—C2—C7—C6	−61.6 (5)	N2—N3—C12—N1	0.5 (4)
C5—C6—C7—C2	−58.6 (5)	N2—N3—C12—S1	−179.9 (3)
C10—C6—C7—C2	61.3 (5)	C11—N1—C12—N3	−0.1 (4)
C3—C2—C1—C9	−61.4 (4)	C17—N1—C12—N3	179.3 (3)
C7—C2—C1—C9	59.4 (5)	C11—N1—C12—S1	−179.7 (2)
C11—C9—C1—C2	178.2 (3)	C17—N1—C12—S1	−0.3 (5)
C10—C9—C1—C2	−57.1 (4)	C13—S1—C12—N3	3.1 (4)
C8—C9—C1—C2	59.5 (4)	C13—S1—C12—N1	−177.3 (3)
C3—C4—C8—C9	60.2 (5)	C16—N4—C14—C13	−69.9 (6)
C5—C4—C8—C9	−59.7 (5)	C15—N4—C14—C13	166.4 (5)
C11—C9—C8—C4	179.4 (3)	S1—C13—C14—N4	−58.1 (5)