4'-Phenyl-3,4-di-hydro-2H-spiro-[naph-tha-lene-1,3'-[1,2,4]triazole]-5'-thione.

In the title mol-ecule, C17H15N3S, the phenyl group makes a dihedral angle of 57.29 (11)° with the mean plane of the triazole ring, which in turn makes an angle of 86.83 (12)° with the plane of the aromatic portion of the tetra-hydro-naphthalene moiety. In the crystal, mol-ecules are linked by weak C-H⋯S hydrogen bonds into supra-molecular chains propagating along the a-axis direction. Weak C-H⋯π inter-actions are also observed.

Related literature

For the synthesis of different triazole thione compounds, see: Wujec et al. (2004 ▶); Zamani et al. (2004 ▶); Pitucha et al. (2007 ▶); Farghaly & El-Kashef (2006 ▶); Guelerman et al. (1998 ▶); Salgin-Gökşen et al. (2007 ▶). For the biological activity of triazole thio­nes, see: Amir & Kumar (2007 ▶); Gokce et al. (2001 ▶); Ezabadi et al. (2008 ▶); Mazzone et al. (1981 ▶); Küçükgüzel et al. (2008 ▶); Dogan et al. (2005 ▶); Kane et al. (1994 ▶); Kane et al. (1988 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H15N3S

M = 293.39

Orthorhombic,

a = 6.2091 (9) Å

b = 13.1804 (19) Å

c = 17.391 (3) Å

V = 1423.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 150 K

0.25 × 0.15 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.80, T max = 0.98

25736 measured reflections

3564 independent reflections

3274 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.085

S = 1.04

3564 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.15 e Å−3

Absolute structure: Flack x determined using 1312 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: −0.02 (3)

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814012409/xu5795sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012409/xu5795Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012409/xu5795Isup3.cml

CCDC reference: 1005633

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H15N3S	F(000) = 616
Mr = 293.39	Dx = 1.369 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9998 reflections
a = 6.2091 (9) Å	θ = 2.3–28.3°
b = 13.1804 (19) Å	µ = 0.22 mm−1
c = 17.391 (3) Å	T = 150 K
V = 1423.3 (4) Å3	Column, orange
Z = 4	0.25 × 0.15 × 0.08 mm

Bruker SMART APEX CCD diffractometer	3564 independent reflections
Radiation source: fine-focus sealed tube	3274 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 8.3660 pixels mm-1	θmax = 28.3°, θmin = 1.9°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −17→17
Tmin = 0.80, Tmax = 0.98	l = −23→23
25736 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.0378P)2 + 0.4193P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.085	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.26 e Å−3
3564 reflections	Δρmin = −0.15 e Å−3
190 parameters	Absolute structure: Flack x determined using 1312 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.02 (3)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.62076 (10)	0.54064 (5)	0.53367 (3)	0.0310 (2)
N1	0.6979 (4)	0.57824 (16)	0.68377 (12)	0.0330 (6)
N2	0.6462 (3)	0.54877 (15)	0.74954 (11)	0.0306 (6)
N3	0.4806 (3)	0.44434 (13)	0.66343 (10)	0.0222 (5)
C1	0.5921 (3)	0.51596 (16)	0.62549 (13)	0.0252 (6)
C2	0.5003 (3)	0.45985 (17)	0.74710 (12)	0.0231 (6)
C3	0.3302 (3)	0.37544 (16)	0.62918 (11)	0.0207 (6)
C4	0.3432 (3)	0.27253 (16)	0.64403 (12)	0.0240 (6)
C5	0.1925 (4)	0.20741 (17)	0.61087 (13)	0.0258 (6)
C6	0.0339 (4)	0.24503 (18)	0.56279 (12)	0.0266 (6)
C7	0.0221 (4)	0.34798 (18)	0.54906 (12)	0.0270 (6)
C8	0.1688 (3)	0.41375 (17)	0.58248 (12)	0.0241 (6)
C9	0.2844 (4)	0.48971 (19)	0.78250 (13)	0.0291 (7)
C10	0.3014 (4)	0.4969 (2)	0.86981 (14)	0.0346 (8)
C11	0.3616 (4)	0.39487 (19)	0.90331 (13)	0.0315 (7)
C12	0.5517 (4)	0.34643 (17)	0.86358 (12)	0.0243 (6)
C13	0.6703 (4)	0.27160 (18)	0.90093 (13)	0.0292 (7)
C14	0.8448 (4)	0.22515 (18)	0.86675 (14)	0.0314 (7)
C15	0.9049 (4)	0.25245 (18)	0.79299 (14)	0.0295 (7)
C16	0.7902 (4)	0.32656 (18)	0.75447 (12)	0.0245 (6)
C17	0.6145 (4)	0.37395 (16)	0.78893 (11)	0.0216 (5)
H4	0.45350	0.24650	0.67640	0.0290*
H5	0.19880	0.13670	0.62140	0.0310*
H6	−0.06640	0.20020	0.53940	0.0320*
H7	−0.08750	0.37400	0.51640	0.0320*
H8	0.15880	0.48470	0.57340	0.0290*
H9A	0.23820	0.55600	0.76150	0.0350*
H9B	0.17420	0.43860	0.76860	0.0350*
H10A	0.41200	0.54780	0.88390	0.0420*
H10B	0.16180	0.51930	0.89140	0.0420*
H11A	0.39580	0.40350	0.95850	0.0380*
H11B	0.23620	0.34880	0.89940	0.0380*
H13	0.62990	0.25190	0.95150	0.0350*
H14	0.92350	0.17460	0.89380	0.0380*
H15	1.02430	0.22040	0.76900	0.0350*
H16	0.83170	0.34540	0.70390	0.0290*

	U11	U22	U33	U12	U13	U23
S1	0.0328 (3)	0.0327 (3)	0.0274 (3)	0.0027 (3)	0.0043 (2)	0.0093 (2)
N1	0.0365 (11)	0.0290 (10)	0.0336 (11)	−0.0093 (9)	−0.0021 (9)	0.0033 (8)
N2	0.0339 (10)	0.0242 (10)	0.0336 (10)	−0.0065 (9)	−0.0046 (9)	−0.0017 (8)
N3	0.0257 (9)	0.0210 (10)	0.0199 (8)	−0.0036 (7)	−0.0028 (7)	0.0013 (7)
C1	0.0243 (10)	0.0216 (11)	0.0298 (11)	0.0001 (8)	−0.0004 (9)	0.0021 (8)
C2	0.0261 (9)	0.0217 (10)	0.0214 (10)	−0.0032 (9)	−0.0022 (8)	−0.0029 (8)
C3	0.0248 (10)	0.0223 (10)	0.0151 (9)	−0.0019 (8)	−0.0002 (8)	−0.0011 (8)
C4	0.0264 (10)	0.0238 (10)	0.0217 (9)	0.0010 (8)	−0.0047 (9)	0.0016 (8)
C5	0.0314 (11)	0.0214 (11)	0.0246 (10)	−0.0027 (9)	−0.0011 (9)	−0.0009 (8)
C6	0.0263 (10)	0.0311 (12)	0.0224 (10)	−0.0040 (9)	−0.0029 (8)	−0.0058 (9)
C7	0.0250 (10)	0.0332 (12)	0.0227 (11)	0.0036 (9)	−0.0061 (9)	−0.0018 (9)
C8	0.0286 (11)	0.0216 (10)	0.0221 (10)	0.0037 (8)	−0.0025 (9)	−0.0014 (8)
C9	0.0282 (11)	0.0299 (12)	0.0293 (11)	0.0035 (9)	−0.0017 (10)	−0.0044 (9)
C10	0.0372 (13)	0.0374 (14)	0.0292 (12)	0.0028 (11)	0.0060 (10)	−0.0088 (10)
C11	0.0334 (12)	0.0390 (14)	0.0221 (11)	−0.0033 (11)	0.0055 (10)	−0.0027 (9)
C12	0.0276 (10)	0.0264 (11)	0.0189 (10)	−0.0076 (8)	0.0006 (8)	−0.0037 (8)
C13	0.0398 (13)	0.0270 (12)	0.0207 (10)	−0.0064 (9)	−0.0014 (9)	0.0010 (9)
C14	0.0389 (13)	0.0255 (11)	0.0299 (11)	−0.0008 (9)	−0.0090 (10)	0.0028 (9)
C15	0.0269 (10)	0.0298 (12)	0.0318 (12)	0.0005 (9)	−0.0013 (9)	−0.0016 (9)
C16	0.0228 (9)	0.0305 (12)	0.0202 (10)	−0.0037 (9)	0.0012 (8)	0.0007 (9)
C17	0.0228 (9)	0.0240 (10)	0.0179 (9)	−0.0048 (9)	−0.0026 (8)	−0.0010 (8)

S1—C1	1.639 (2)	C13—C14	1.379 (3)
N1—N2	1.250 (3)	C14—C15	1.384 (3)
N1—C1	1.460 (3)	C15—C16	1.382 (3)
N2—C2	1.482 (3)	C16—C17	1.393 (3)
N3—C1	1.344 (3)	C4—H4	0.9500
N3—C2	1.475 (3)	C5—H5	0.9500
N3—C3	1.432 (3)	C6—H6	0.9500
C2—C9	1.527 (3)	C7—H7	0.9500
C2—C17	1.521 (3)	C8—H8	0.9500
C3—C4	1.383 (3)	C9—H9A	0.9900
C3—C8	1.385 (3)	C9—H9B	0.9900
C4—C5	1.395 (3)	C10—H10A	0.9900
C5—C6	1.384 (3)	C10—H10B	0.9900
C6—C7	1.380 (3)	C11—H11A	0.9900
C7—C8	1.385 (3)	C11—H11B	0.9900
C9—C10	1.525 (3)	C13—H13	0.9500
C10—C11	1.513 (4)	C14—H14	0.9500
C11—C12	1.509 (3)	C15—H15	0.9500
C12—C13	1.392 (3)	C16—H16	0.9500
C12—C17	1.403 (3)
N2—N1—C1	110.2 (2)	C12—C17—C16	120.0 (2)
N1—N2—C2	112.12 (19)	C3—C4—H4	120.00
C1—N3—C2	110.15 (17)	C5—C4—H4	120.00
C1—N3—C3	125.25 (18)	C4—C5—H5	120.00
C2—N3—C3	123.53 (17)	C6—C5—H5	120.00
S1—C1—N1	121.04 (16)	C5—C6—H6	120.00
S1—C1—N3	132.35 (17)	C7—C6—H6	120.00
N1—C1—N3	106.61 (19)	C6—C7—H7	120.00
N2—C2—N3	100.87 (16)	C8—C7—H7	120.00
N2—C2—C9	108.74 (18)	C3—C8—H8	120.00
N2—C2—C17	106.86 (16)	C7—C8—H8	120.00
N3—C2—C9	111.15 (17)	C2—C9—H9A	109.00
N3—C2—C17	114.04 (17)	C2—C9—H9B	109.00
C9—C2—C17	114.10 (18)	C10—C9—H9A	109.00
N3—C3—C4	120.40 (17)	C10—C9—H9B	109.00
N3—C3—C8	118.97 (19)	H9A—C9—H9B	108.00
C4—C3—C8	120.61 (19)	C9—C10—H10A	110.00
C3—C4—C5	119.16 (19)	C9—C10—H10B	110.00
C4—C5—C6	120.5 (2)	C11—C10—H10A	110.00
C5—C6—C7	119.7 (2)	C11—C10—H10B	110.00
C6—C7—C8	120.5 (2)	H10A—C10—H10B	108.00
C3—C8—C7	119.6 (2)	C10—C11—H11A	109.00
C2—C9—C10	110.90 (19)	C10—C11—H11B	109.00
C9—C10—C11	110.2 (2)	C12—C11—H11A	109.00
C10—C11—C12	113.14 (19)	C12—C11—H11B	109.00
C11—C12—C13	120.0 (2)	H11A—C11—H11B	108.00
C11—C12—C17	122.1 (2)	C12—C13—H13	119.00
C13—C12—C17	117.9 (2)	C14—C13—H13	119.00
C12—C13—C14	122.0 (2)	C13—C14—H14	120.00
C13—C14—C15	119.7 (2)	C15—C14—H14	120.00
C14—C15—C16	119.6 (2)	C14—C15—H15	120.00
C15—C16—C17	120.8 (2)	C16—C15—H15	120.00
C2—C17—C12	120.4 (2)	C15—C16—H16	120.00
C2—C17—C16	119.55 (18)	C17—C16—H16	120.00
C1—N1—N2—C2	1.3 (3)	N3—C2—C17—C16	38.4 (3)
N2—N1—C1—S1	176.99 (17)	C9—C2—C17—C12	−16.1 (3)
N2—N1—C1—N3	−2.6 (3)	C9—C2—C17—C16	167.6 (2)
N1—N2—C2—N3	0.3 (2)	N3—C3—C4—C5	178.98 (19)
N1—N2—C2—C9	−116.6 (2)	C8—C3—C4—C5	0.5 (3)
N1—N2—C2—C17	119.8 (2)	N3—C3—C8—C7	−179.93 (18)
C2—N3—C1—S1	−176.77 (17)	C4—C3—C8—C7	−1.4 (3)
C2—N3—C1—N1	2.7 (2)	C3—C4—C5—C6	1.0 (3)
C3—N3—C1—S1	−8.3 (3)	C4—C5—C6—C7	−1.5 (3)
C3—N3—C1—N1	171.17 (19)	C5—C6—C7—C8	0.6 (3)
C1—N3—C2—N2	−2.0 (2)	C6—C7—C8—C3	0.9 (3)
C1—N3—C2—C9	113.2 (2)	C2—C9—C10—C11	−61.8 (3)
C1—N3—C2—C17	−116.1 (2)	C9—C10—C11—C12	49.2 (3)
C3—N3—C2—N2	−170.63 (17)	C10—C11—C12—C13	159.1 (2)
C3—N3—C2—C9	−55.5 (3)	C10—C11—C12—C17	−21.2 (3)
C3—N3—C2—C17	75.2 (2)	C11—C12—C13—C14	179.9 (2)
C1—N3—C3—C4	130.6 (2)	C17—C12—C13—C14	0.1 (4)
C1—N3—C3—C8	−50.9 (3)	C11—C12—C17—C2	4.2 (3)
C2—N3—C3—C4	−62.4 (3)	C11—C12—C17—C16	−179.6 (2)
C2—N3—C3—C8	116.1 (2)	C13—C12—C17—C2	−176.1 (2)
N2—C2—C9—C10	−74.6 (2)	C13—C12—C17—C16	0.2 (3)
N3—C2—C9—C10	175.21 (19)	C12—C13—C14—C15	−0.4 (4)
C17—C2—C9—C10	44.5 (3)	C13—C14—C15—C16	0.4 (4)
N2—C2—C17—C12	104.1 (2)	C14—C15—C16—C17	−0.2 (4)
N2—C2—C17—C16	−72.2 (2)	C15—C16—C17—C2	176.1 (2)
N3—C2—C17—C12	−145.4 (2)	C15—C16—C17—C12	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···S1i	0.95	2.86	3.568 (3)	132
C6—H6···Cg3ii	0.95	2.84	3.602 (2)	138
C16—H16···Cg3iii	0.95	2.90	3.676 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the benzene ring of the 1,2,3,4-tetra­hydro­naphthalene group.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯S1i	0.95	2.86	3.568 (3)	132
C6—H6⋯Cg3ii	0.95	2.84	3.602 (2)	138
C16—H16⋯Cg3iii	0.95	2.90	3.676 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) .