4-Phenyl-1,2,4-tri-aza-spiro-[4.5]dec-1-ene-3-thione.

In the title compound, C13H15N3S, the 4,5-di-hydro-3H-1,2,4-triazole ring is nearly planar [maximum deviation = 0.020 (1) Å], while the cyclo-hexane ring adopts a chair conformation. The dihedral angle between the 4,5-di-hydro-3H-1,2,4-triazole ring and the phenyl ring is 74.68 (7)°. No specific inter-molecular inter-actions are discerned in the crystal packing.

Related literature

For wide-spectrum medicinal applications of spiro compounds incorporating heterocyclic substructures, see: Patil et al. (2010 ▶); Pawar et al. (2009 ▶); Thadhaney et al. (2010 ▶); Chin et al. (2008 ▶); Wang et al. (2007 ▶); Chande et al. (2005 ▶); Obniska et al. (2006 ▶); Kamiński et al. (2008 ▶); Sarma et al. (2010 ▶); Shimakawa et al. (2003 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H15N3S

M = 245.34

Orthorhombic,

a = 9.4952 (9) Å

b = 7.4845 (7) Å

c = 34.692 (3) Å

V = 2465.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.24 mm−1

T = 150 K

0.28 × 0.22 × 0.17 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.810, T max = 0.960

41202 measured reflections

3168 independent reflections

2899 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.104

S = 1.10

3168 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019120/tk5237sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019120/tk5237Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019120/tk5237Isup3.cml

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

C13H15N3S	F(000) = 1040
Mr = 245.34	Dx = 1.322 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9973 reflections
a = 9.4952 (9) Å	θ = 2.5–28.6°
b = 7.4845 (7) Å	µ = 0.24 mm−1
c = 34.692 (3) Å	T = 150 K
V = 2465.5 (4) Å3	Block, red-brown
Z = 8	0.28 × 0.22 × 0.17 mm

Bruker SMART APEX CCD diffractometer	3168 independent reflections
Radiation source: fine-focus sealed tube	2899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
Detector resolution: 8.3660 pixels mm-1	θmax = 28.7°, θmin = 2.4°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −10→10
Tmin = 0.810, Tmax = 0.960	l = −46→46
41202 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H-atom parameters constrained
S = 1.10	W = 1/[Σ2(FO2) + (0.0483P)2 + 1.0447P] where P = (FO2 + 2FC2)/3
3168 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.25 e Å−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	0.53002 (4)	1.40579 (5)	0.84564 (2)	0.0310 (1)
N1	0.50442 (11)	1.06645 (14)	0.87249 (3)	0.0199 (3)
N2	0.53364 (11)	1.27385 (15)	0.91860 (3)	0.0252 (3)
N3	0.51796 (11)	1.13018 (15)	0.93661 (3)	0.0233 (3)
C1	0.52216 (12)	1.24250 (17)	0.87698 (4)	0.0219 (3)
C2	0.49469 (12)	0.97820 (16)	0.91027 (3)	0.0188 (3)
C3	0.60868 (13)	0.83732 (18)	0.91727 (4)	0.0241 (3)
C4	0.59589 (15)	0.75735 (19)	0.95773 (4)	0.0282 (4)
C5	0.44880 (15)	0.68348 (18)	0.96539 (4)	0.0280 (4)
C6	0.33484 (14)	0.82248 (17)	0.95781 (3)	0.0240 (3)
C7	0.34706 (13)	0.90101 (16)	0.91725 (3)	0.0209 (3)
C8	0.47802 (13)	0.97938 (17)	0.83642 (3)	0.0208 (3)
C9	0.58094 (15)	0.87142 (18)	0.82019 (4)	0.0273 (4)
C10	0.55240 (17)	0.7858 (2)	0.78557 (4)	0.0346 (4)
C11	0.42447 (19)	0.8099 (2)	0.76734 (4)	0.0377 (5)
C12	0.32316 (18)	0.9190 (2)	0.78367 (4)	0.0369 (4)
C13	0.34905 (15)	1.00429 (19)	0.81847 (4)	0.0283 (4)
H3A	0.70270	0.89270	0.91420	0.0290*
H3B	0.59970	0.74110	0.89790	0.0290*
H4A	0.66580	0.66010	0.96070	0.0340*
H4B	0.61770	0.85060	0.97710	0.0340*
H5A	0.43240	0.57840	0.94860	0.0340*
H5B	0.44270	0.64330	0.99250	0.0340*
H6A	0.34290	0.91980	0.97700	0.0290*
H6B	0.24110	0.76650	0.96090	0.0290*
H7A	0.27600	0.99650	0.91390	0.0250*
H7B	0.32760	0.80660	0.89800	0.0250*
H9	0.66940	0.85640	0.83260	0.0330*
H10	0.62130	0.71000	0.77430	0.0410*
H11	0.40610	0.75150	0.74360	0.0450*
H12	0.23540	0.93560	0.77100	0.0440*
H13	0.27940	1.07870	0.82980	0.0340*

	U11	U22	U33	U12	U13	U23
S1	0.0373 (2)	0.0214 (2)	0.0344 (2)	−0.0050 (1)	0.0002 (1)	0.0067 (1)
N1	0.0234 (5)	0.0179 (5)	0.0183 (5)	−0.0008 (4)	−0.0003 (4)	0.0003 (4)
N2	0.0254 (5)	0.0214 (5)	0.0287 (6)	−0.0028 (4)	0.0010 (4)	−0.0045 (4)
N3	0.0255 (5)	0.0209 (5)	0.0235 (5)	−0.0009 (4)	−0.0004 (4)	−0.0056 (4)
C1	0.0190 (5)	0.0195 (6)	0.0272 (6)	−0.0014 (4)	0.0011 (4)	−0.0011 (5)
C2	0.0230 (5)	0.0172 (6)	0.0162 (5)	−0.0001 (4)	−0.0014 (4)	−0.0013 (4)
C3	0.0240 (6)	0.0248 (6)	0.0235 (6)	0.0054 (5)	−0.0030 (5)	−0.0015 (5)
C4	0.0337 (7)	0.0276 (7)	0.0234 (6)	0.0075 (6)	−0.0077 (5)	0.0000 (5)
C5	0.0406 (7)	0.0218 (6)	0.0215 (6)	0.0034 (5)	−0.0025 (5)	0.0022 (5)
C6	0.0308 (6)	0.0208 (6)	0.0204 (6)	−0.0017 (5)	0.0018 (5)	0.0011 (4)
C7	0.0216 (5)	0.0200 (5)	0.0210 (6)	−0.0004 (5)	−0.0011 (4)	0.0011 (4)
C8	0.0263 (6)	0.0189 (6)	0.0172 (5)	−0.0034 (5)	0.0008 (4)	0.0014 (4)
C9	0.0313 (7)	0.0269 (6)	0.0236 (6)	0.0007 (5)	0.0058 (5)	0.0003 (5)
C10	0.0504 (9)	0.0281 (7)	0.0252 (7)	−0.0031 (6)	0.0146 (6)	−0.0030 (5)
C11	0.0607 (10)	0.0340 (8)	0.0185 (6)	−0.0168 (7)	0.0013 (6)	−0.0025 (5)
C12	0.0434 (8)	0.0404 (8)	0.0268 (7)	−0.0093 (7)	−0.0107 (6)	0.0008 (6)
C13	0.0302 (7)	0.0298 (7)	0.0250 (6)	−0.0013 (5)	−0.0029 (5)	0.0006 (5)

S1—C1	1.6375 (14)	C11—C12	1.383 (2)
N1—C1	1.3375 (17)	C12—C13	1.388 (2)
N1—C2	1.4706 (15)	C3—H3A	0.9900
N1—C8	1.4330 (15)	C3—H3B	0.9900
N2—N3	1.2525 (16)	C4—H4A	0.9900
N2—C1	1.4669 (17)	C4—H4B	0.9900
N3—C2	1.4757 (16)	C5—H5A	0.9900
C2—C3	1.5305 (17)	C5—H5B	0.9900
C2—C7	1.5354 (17)	C6—H6A	0.9900
C3—C4	1.531 (2)	C6—H6B	0.9900
C4—C5	1.525 (2)	C7—H7A	0.9900
C5—C6	1.5239 (19)	C7—H7B	0.9900
C6—C7	1.5293 (15)	C9—H9	0.9500
C8—C9	1.3874 (19)	C10—H10	0.9500
C8—C13	1.3864 (19)	C11—H11	0.9500
C9—C10	1.388 (2)	C12—H12	0.9500
C10—C11	1.381 (2)	C13—H13	0.9500
C1—N1—C2	110.28 (10)	H3A—C3—H3B	108.00
C1—N1—C8	124.87 (11)	C3—C4—H4A	109.00
C2—N1—C8	124.27 (10)	C3—C4—H4B	109.00
N3—N2—C1	110.17 (10)	C5—C4—H4A	109.00
N2—N3—C2	111.76 (10)	C5—C4—H4B	109.00
S1—C1—N1	131.58 (11)	H4A—C4—H4B	108.00
S1—C1—N2	122.06 (10)	C4—C5—H5A	109.00
N1—C1—N2	106.36 (11)	C4—C5—H5B	109.00
N1—C2—N3	101.32 (9)	C6—C5—H5A	109.00
N1—C2—C3	113.98 (10)	C6—C5—H5B	109.00
N1—C2—C7	111.53 (9)	H5A—C5—H5B	108.00
N3—C2—C3	109.08 (9)	C5—C6—H6A	109.00
N3—C2—C7	109.21 (9)	C5—C6—H6B	109.00
C3—C2—C7	111.19 (10)	C7—C6—H6A	109.00
C2—C3—C4	111.03 (10)	C7—C6—H6B	109.00
C3—C4—C5	111.97 (11)	H6A—C6—H6B	108.00
C4—C5—C6	111.88 (11)	C2—C7—H7A	109.00
C5—C6—C7	111.55 (10)	C2—C7—H7B	109.00
C2—C7—C6	111.04 (10)	C6—C7—H7A	110.00
N1—C8—C9	119.74 (11)	C6—C7—H7B	109.00
N1—C8—C13	119.05 (11)	H7A—C7—H7B	108.00
C9—C8—C13	121.21 (11)	C8—C9—H9	120.00
C8—C9—C10	118.85 (13)	C10—C9—H9	121.00
C9—C10—C11	120.50 (14)	C9—C10—H10	120.00
C10—C11—C12	120.08 (13)	C11—C10—H10	120.00
C11—C12—C13	120.31 (15)	C10—C11—H11	120.00
C8—C13—C12	119.04 (13)	C12—C11—H11	120.00
C2—C3—H3A	109.00	C11—C12—H12	120.00
C2—C3—H3B	109.00	C13—C12—H12	120.00
C4—C3—H3A	110.00	C8—C13—H13	121.00
C4—C3—H3B	109.00	C12—C13—H13	120.00
C2—N1—C1—S1	−175.88 (10)	N2—N3—C2—C7	−116.28 (11)
C2—N1—C1—N2	3.52 (12)	N1—C2—C3—C4	177.48 (10)
C8—N1—C1—S1	−4.33 (19)	N3—C2—C3—C4	65.07 (13)
C8—N1—C1—N2	175.07 (10)	C7—C2—C3—C4	−55.43 (13)
C1—N1—C2—N3	−3.14 (12)	N1—C2—C7—C6	−175.60 (10)
C1—N1—C2—C3	−120.14 (11)	N3—C2—C7—C6	−64.44 (12)
C1—N1—C2—C7	112.94 (11)	C3—C2—C7—C6	55.98 (13)
C8—N1—C2—N3	−174.76 (10)	C2—C3—C4—C5	54.36 (15)
C8—N1—C2—C3	68.24 (14)	C3—C4—C5—C6	−53.80 (15)
C8—N1—C2—C7	−58.67 (14)	C4—C5—C6—C7	54.12 (14)
C1—N1—C8—C9	110.43 (14)	C5—C6—C7—C2	−55.15 (13)
C1—N1—C8—C13	−69.89 (16)	N1—C8—C9—C10	178.89 (12)
C2—N1—C8—C9	−79.16 (15)	C13—C8—C9—C10	−0.8 (2)
C2—N1—C8—C13	100.51 (14)	N1—C8—C13—C12	−179.57 (12)
C1—N2—N3—C2	0.53 (13)	C9—C8—C13—C12	0.1 (2)
N3—N2—C1—S1	176.89 (9)	C8—C9—C10—C11	1.0 (2)
N3—N2—C1—N1	−2.58 (13)	C9—C10—C11—C12	−0.5 (2)
N2—N3—C2—N1	1.50 (12)	C10—C11—C12—C13	−0.2 (2)
N2—N3—C2—C3	122.02 (11)	C11—C12—C13—C8	0.4 (2)