4-Amino-3-(1-naphthyl-oxymeth-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(13)H(12)N(4)OS, the dihedral angle between the triazole and naphthalene ring systems is 67.42 (5)°. In the crystal, adjacent mol-ecules are linked via two pairs of inter-molecular N-H⋯S inter-actions, forming R(2) (2)(8) and R(2) (2)(10) ring motifs. Weak C-H⋯S inter-actions generate infinite chains along [001] and the structure is further consolidated by C-H⋯π bonds and aromatic π⋯π stacking inter-actions [distance between the centroids of the triazole rings = 3.2479 (7) Å].

Related literature

For general background to and the pharmacological activity of triazole derivatives, see: Amir et al. (2008 ▶); Sztanke et al. (2008 ▶); Kuş et al. (2008 ▶); Padmavathi et al. (2008 ▶); Isloor et al. (2009 ▶). For a related structure, see: Fun et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the preparation, see: Suresh (1992 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C13H12N4OS

M = 272.33

Monoclinic,

a = 7.0023 (1) Å

b = 24.0785 (4) Å

c = 8.0915 (1) Å

β = 113.404 (1)°

V = 1252.02 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.38 × 0.23 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.908, T max = 0.983

24326 measured reflections

5826 independent reflections

4223 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.122

S = 1.03

5826 reflections

220 parameters

All H-atom parameters refined

Δρmax = 0.51 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809051368/hb5255sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051368/hb5255Isup2.hkl

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

C13H12N4OS	F(000) = 568
Mr = 272.33	Dx = 1.445 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5692 reflections
a = 7.0023 (1) Å	θ = 2.9–35.1°
b = 24.0785 (4) Å	µ = 0.26 mm−1
c = 8.0915 (1) Å	T = 100 K
β = 113.404 (1)°	Plate, yellow
V = 1252.02 (3) Å3	0.38 × 0.23 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	5826 independent reflections
Radiation source: fine-focus sealed tube	4223 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 35.8°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.908, Tmax = 0.983	k = −39→38
24326 measured reflections	l = −13→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.214P] where P = (Fo2 + 2Fc2)/3
5826 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.00629 (5)	0.044619 (13)	0.25791 (4)	0.01810 (8)
O1	0.52129 (13)	−0.11362 (4)	0.14188 (11)	0.01666 (16)
N1	0.22651 (15)	−0.04341 (4)	0.46060 (13)	0.01481 (17)
N2	0.38889 (16)	−0.07854 (4)	0.47914 (13)	0.01636 (18)
N3	0.33179 (15)	−0.01814 (4)	0.25913 (12)	0.01411 (17)
N4	0.37675 (18)	0.01243 (5)	0.13172 (14)	0.0193 (2)
C1	0.18602 (17)	−0.00623 (5)	0.32721 (14)	0.01419 (19)
C2	0.44981 (17)	−0.06189 (5)	0.35421 (15)	0.01418 (19)
C3	0.61978 (18)	−0.08762 (5)	0.31417 (15)	0.0162 (2)
C4	0.65096 (17)	−0.13872 (5)	0.07391 (14)	0.01338 (19)
C5	0.86351 (18)	−0.14187 (5)	0.16169 (16)	0.0165 (2)
C6	0.98108 (19)	−0.16981 (5)	0.07908 (17)	0.0195 (2)
C7	0.88492 (19)	−0.19351 (5)	−0.08729 (17)	0.0187 (2)
C8	0.66644 (18)	−0.19040 (5)	−0.18076 (15)	0.01484 (19)
C9	0.5615 (2)	−0.21540 (5)	−0.35253 (16)	0.0185 (2)
C10	0.3499 (2)	−0.21323 (5)	−0.43817 (16)	0.0199 (2)
C11	0.2304 (2)	−0.18580 (5)	−0.35758 (16)	0.0178 (2)
C12	0.32576 (18)	−0.16061 (5)	−0.19258 (15)	0.01452 (19)
C13	0.54499 (17)	−0.16261 (4)	−0.10061 (14)	0.01255 (18)
H3A	0.693 (2)	−0.1148 (6)	0.405 (2)	0.013 (3)*
H3B	0.715 (2)	−0.0602 (6)	0.310 (2)	0.015 (4)*
H5A	0.940 (3)	−0.1254 (7)	0.279 (2)	0.022 (4)*
H6A	1.131 (3)	−0.1723 (7)	0.134 (2)	0.029 (4)*
H7A	0.962 (3)	−0.2110 (7)	−0.143 (2)	0.026 (4)*
H9A	0.647 (3)	−0.2335 (7)	−0.404 (2)	0.031 (5)*
H10A	0.288 (3)	−0.2318 (7)	−0.550 (2)	0.028 (4)*
H11A	0.080 (3)	−0.1865 (7)	−0.414 (2)	0.023 (4)*
H12A	0.240 (3)	−0.1418 (7)	−0.142 (2)	0.022 (4)*
H1N1	0.162 (3)	−0.0455 (7)	0.536 (3)	0.031 (5)*
H1N4	0.284 (3)	0.0023 (8)	0.022 (3)	0.035 (5)*
H2N4	0.354 (3)	0.0475 (8)	0.153 (3)	0.035 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01841 (14)	0.02112 (15)	0.01629 (13)	0.00540 (10)	0.00852 (11)	0.00193 (10)
O1	0.0150 (4)	0.0207 (4)	0.0148 (3)	0.0010 (3)	0.0065 (3)	−0.0072 (3)
N1	0.0161 (4)	0.0159 (4)	0.0151 (4)	0.0006 (3)	0.0090 (4)	−0.0001 (3)
N2	0.0187 (4)	0.0159 (4)	0.0170 (4)	0.0015 (4)	0.0098 (4)	−0.0006 (3)
N3	0.0157 (4)	0.0156 (4)	0.0129 (4)	0.0004 (3)	0.0077 (3)	−0.0001 (3)
N4	0.0248 (5)	0.0216 (5)	0.0153 (4)	0.0013 (4)	0.0122 (4)	0.0031 (4)
C1	0.0144 (5)	0.0157 (5)	0.0133 (4)	−0.0014 (4)	0.0064 (4)	−0.0022 (3)
C2	0.0151 (5)	0.0143 (5)	0.0138 (4)	−0.0005 (4)	0.0064 (4)	−0.0029 (3)
C3	0.0157 (5)	0.0191 (5)	0.0135 (4)	0.0012 (4)	0.0056 (4)	−0.0044 (4)
C4	0.0141 (4)	0.0139 (5)	0.0140 (4)	0.0013 (3)	0.0076 (4)	−0.0015 (3)
C5	0.0148 (5)	0.0188 (5)	0.0156 (5)	0.0000 (4)	0.0057 (4)	−0.0023 (4)
C6	0.0145 (5)	0.0233 (6)	0.0218 (5)	0.0027 (4)	0.0085 (4)	−0.0006 (4)
C7	0.0187 (5)	0.0193 (5)	0.0218 (5)	0.0035 (4)	0.0118 (5)	−0.0007 (4)
C8	0.0187 (5)	0.0130 (5)	0.0159 (4)	0.0008 (4)	0.0100 (4)	0.0001 (4)
C9	0.0259 (6)	0.0157 (5)	0.0172 (5)	−0.0006 (4)	0.0120 (5)	−0.0034 (4)
C10	0.0261 (6)	0.0174 (5)	0.0153 (5)	−0.0032 (4)	0.0072 (5)	−0.0039 (4)
C11	0.0185 (5)	0.0177 (5)	0.0159 (5)	−0.0026 (4)	0.0054 (4)	0.0000 (4)
C12	0.0156 (5)	0.0137 (5)	0.0148 (4)	−0.0003 (4)	0.0066 (4)	−0.0003 (4)
C13	0.0145 (5)	0.0111 (4)	0.0129 (4)	0.0004 (3)	0.0065 (4)	−0.0003 (3)

S1—C1	1.6842 (12)	C5—C6	1.4192 (16)
O1—C4	1.3743 (12)	C5—H5A	0.971 (17)
O1—C3	1.4308 (13)	C6—C7	1.3678 (18)
N1—C1	1.3431 (14)	C6—H6A	0.964 (18)
N1—N2	1.3768 (13)	C7—C8	1.4138 (17)
N1—H1N1	0.894 (19)	C7—H7A	0.931 (17)
N2—C2	1.3066 (14)	C8—C9	1.4223 (16)
N3—C1	1.3691 (13)	C8—C13	1.4246 (15)
N3—C2	1.3710 (15)	C9—C10	1.3648 (19)
N3—N4	1.4005 (13)	C9—H9A	0.964 (17)
N4—H1N4	0.90 (2)	C10—C11	1.4123 (17)
N4—H2N4	0.888 (19)	C10—H10A	0.947 (18)
C2—C3	1.4872 (15)	C11—C12	1.3740 (16)
C3—H3A	0.966 (15)	C11—H11A	0.967 (17)
C3—H3B	0.948 (15)	C12—C13	1.4160 (16)
C4—C5	1.3732 (16)	C12—H12A	0.960 (16)
C4—C13	1.4294 (15)
C4—O1—C3	116.29 (9)	C4—C5—H5A	123.0 (10)
C1—N1—N2	113.50 (9)	C6—C5—H5A	117.3 (10)
C1—N1—H1N1	125.7 (12)	C7—C6—C5	120.69 (11)
N2—N1—H1N1	120.7 (12)	C7—C6—H6A	116.6 (10)
C2—N2—N1	103.67 (9)	C5—C6—H6A	122.6 (10)
C1—N3—C2	108.34 (9)	C6—C7—C8	120.62 (10)
C1—N3—N4	127.42 (10)	C6—C7—H7A	121.0 (11)
C2—N3—N4	123.73 (9)	C8—C7—H7A	118.4 (11)
N3—N4—H1N4	107.3 (12)	C7—C8—C9	121.97 (10)
N3—N4—H2N4	104.3 (12)	C7—C8—C13	119.74 (10)
H1N4—N4—H2N4	109.4 (18)	C9—C8—C13	118.27 (10)
N1—C1—N3	103.33 (9)	C10—C9—C8	121.01 (10)
N1—C1—S1	130.05 (8)	C10—C9—H9A	122.4 (11)
N3—C1—S1	126.60 (9)	C8—C9—H9A	116.6 (11)
N2—C2—N3	111.15 (10)	C9—C10—C11	120.41 (11)
N2—C2—C3	125.18 (11)	C9—C10—H10A	117.4 (10)
N3—C2—C3	123.64 (10)	C11—C10—H10A	122.2 (10)
O1—C3—C2	106.07 (9)	C12—C11—C10	120.45 (11)
O1—C3—H3A	110.6 (9)	C12—C11—H11A	119.1 (10)
C2—C3—H3A	109.9 (8)	C10—C11—H11A	120.4 (10)
O1—C3—H3B	110.0 (9)	C11—C12—C13	120.17 (10)
C2—C3—H3B	110.6 (9)	C11—C12—H12A	118.5 (10)
H3A—C3—H3B	109.6 (13)	C13—C12—H12A	121.4 (10)
C5—C4—O1	124.75 (10)	C12—C13—C8	119.68 (10)
C5—C4—C13	121.29 (9)	C12—C13—C4	122.31 (9)
O1—C4—C13	113.96 (9)	C8—C13—C4	117.98 (10)
C4—C5—C6	119.66 (11)
C1—N1—N2—C2	0.50 (13)	C4—C5—C6—C7	0.18 (19)
N2—N1—C1—N3	−0.61 (12)	C5—C6—C7—C8	0.32 (19)
N2—N1—C1—S1	−179.18 (9)	C6—C7—C8—C9	−178.92 (12)
C2—N3—C1—N1	0.48 (12)	C6—C7—C8—C13	−0.36 (18)
N4—N3—C1—N1	−171.51 (10)	C7—C8—C9—C10	178.15 (11)
C2—N3—C1—S1	179.11 (9)	C13—C8—C9—C10	−0.43 (17)
N4—N3—C1—S1	7.12 (17)	C8—C9—C10—C11	0.18 (18)
N1—N2—C2—N3	−0.17 (12)	C9—C10—C11—C12	0.48 (18)
N1—N2—C2—C3	−178.26 (11)	C10—C11—C12—C13	−0.87 (17)
C1—N3—C2—N2	−0.20 (13)	C11—C12—C13—C8	0.61 (16)
N4—N3—C2—N2	172.15 (10)	C11—C12—C13—C4	−177.82 (11)
C1—N3—C2—C3	177.92 (10)	C7—C8—C13—C12	−178.58 (11)
N4—N3—C2—C3	−9.73 (17)	C9—C8—C13—C12	0.03 (16)
C4—O1—C3—C2	177.76 (9)	C7—C8—C13—C4	−0.08 (16)
N2—C2—C3—O1	110.95 (12)	C9—C8—C13—C4	178.53 (10)
N3—C2—C3—O1	−66.91 (14)	C5—C4—C13—C12	179.03 (11)
C3—O1—C4—C5	2.21 (16)	O1—C4—C13—C12	−0.50 (15)
C3—O1—C4—C13	−178.28 (9)	C5—C4—C13—C8	0.57 (16)
O1—C4—C5—C6	178.85 (11)	O1—C4—C13—C8	−178.96 (9)
C13—C4—C5—C6	−0.63 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S1i	0.89 (2)	2.39 (2)	3.2857 (11)	176.2 (14)
N4—H1N4···S1ii	0.90 (2)	2.62 (2)	3.5075 (12)	167.3 (19)
C12—H12A···S1ii	0.96 (2)	2.836 (18)	3.5368 (13)	130.3 (12)
C9—H9A···Cg1iii	0.964 (17)	2.794 (18)	3.6345 (14)	146.8 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S1i	0.89 (2)	2.39 (2)	3.2857 (11)	176.2 (14)
N4—H1N4⋯S1ii	0.90 (2)	2.62 (2)	3.5075 (12)	167.3 (19)
C12—H12A⋯S1ii	0.96 (2)	2.836 (18)	3.5368 (13)	130.3 (12)
C9—H9A⋯Cg1iii	0.964 (17)	2.794 (18)	3.6345 (14)	146.8 (14)

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of C4–C8/C13 ring.