(E)-4-{[(3-Propyl-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-4-yl)imino]-meth-yl}-3-(p-tol-yl)-1,2,3-oxadiazol-3-ium-5-olate.

The title compound, C(15)H(16)N(6)O(2)S, exists in a trans configuration with respect to the acyclic N=C bond. The 1,2,3-oxadiazol-3-ium ring makes dihedral angles of 10.59 (8) and 73.94 (8)°, respectively, with the 1,2,4-triazole and benzene rings. The mol-ecular structure is stabilized by an intra-molecular C-H⋯S hydrogen bond, which generates an S(6) ring motif. In the crystal, mol-ecules are linked into inversion dimers by pairs of inter-molecular N-H⋯S hydrogen bonds, generating eight-membered R(2) (2)(8) ring motifs. The dimers are further connected by C-H⋯O hydrogen bonds, forming a sheet parallel to the bc plane. The ethyl group is disordered over two sets of sites with occupancies of 0.744 (7) and 0.256 (7).

Related literature

For general background to and applications of sydnone derivatives, see: Baker et al. (1949 ▶); Hedge et al. (2008 ▶); Rai et al. (2008 ▶); Kalluraya et al. (2002 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For a related structure, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C15H16N6O2S

M = 344.40

Monoclinic,

a = 13.4220 (11) Å

b = 6.2411 (5) Å

c = 21.1374 (16) Å

β = 104.575 (2)°

V = 1713.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.51 × 0.17 × 0.08 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.865, T max = 0.983

18912 measured reflections

5003 independent reflections

3637 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.123

S = 1.04

5003 reflections

243 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.21 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/S1600536811037287/is2776sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037287/is2776Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037287/is2776Isup3.cml

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

C15H16N6O2S	F(000) = 720
Mr = 344.40	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5356 reflections
a = 13.4220 (11) Å	θ = 2.2–27.6°
b = 6.2411 (5) Å	µ = 0.21 mm−1
c = 21.1374 (16) Å	T = 296 K
β = 104.575 (2)°	Needle, colourless
V = 1713.7 (2) Å3	0.51 × 0.17 × 0.08 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	5003 independent reflections
Radiation source: fine-focus sealed tube	3637 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.865, Tmax = 0.983	k = −8→8
18912 measured reflections	l = −29→29

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0622P)2 + 0.2043P] where P = (Fo2 + 2Fc2)/3
5003 reflections	(Δ/σ)max = 0.001
243 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 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	Occ. (<1)
S1	1.08849 (3)	1.22661 (6)	0.061779 (16)	0.04353 (11)
O1	1.07417 (9)	0.32936 (18)	0.22957 (5)	0.0546 (3)
O2	0.90860 (8)	0.41866 (18)	0.18192 (5)	0.0532 (3)
N1	1.15527 (9)	0.59146 (19)	0.20345 (5)	0.0412 (3)
N2	1.17089 (11)	0.4104 (2)	0.23528 (7)	0.0560 (3)
N3	0.93160 (9)	0.8734 (2)	0.11642 (5)	0.0419 (3)
N4	0.90503 (8)	1.05639 (18)	0.07899 (5)	0.0372 (2)
N5	0.88806 (10)	1.3345 (2)	0.01976 (6)	0.0487 (3)
N6	0.78985 (10)	1.2811 (2)	0.02200 (7)	0.0552 (3)
C1	1.26773 (13)	0.9030 (3)	0.23096 (9)	0.0590 (4)
H1A	1.2297	0.9496	0.2595	0.071*
C2	1.34955 (13)	1.0220 (3)	0.22159 (10)	0.0661 (5)
H2A	1.3667	1.1500	0.2443	0.079*
C3	1.40617 (13)	0.9549 (4)	0.17941 (9)	0.0676 (5)
C4	1.37997 (16)	0.7634 (4)	0.14644 (10)	0.0825 (7)
H4A	1.4184	0.7155	0.1182	0.099*
C5	1.29812 (14)	0.6417 (4)	0.15446 (9)	0.0684 (5)
H5A	1.2804	0.5142	0.1316	0.082*
C6	1.24376 (11)	0.7144 (2)	0.19713 (7)	0.0443 (3)
C7	0.99772 (11)	0.4668 (2)	0.19272 (6)	0.0411 (3)
C8	1.05554 (10)	0.6411 (2)	0.17668 (6)	0.0361 (3)
C9	1.02620 (10)	0.8309 (2)	0.13889 (6)	0.0386 (3)
H9A	1.0762	0.9226	0.1308	0.046*
C10	0.96113 (10)	1.2042 (2)	0.05372 (6)	0.0373 (3)
C11	0.80236 (11)	1.1116 (3)	0.05860 (7)	0.0474 (3)
C12	0.71870 (12)	0.9897 (3)	0.07693 (11)	0.0679 (5)
H12A	0.6594	1.0797	0.0726	0.081*	0.744 (7)
H12B	0.7412	0.9443	0.1217	0.081*	0.744 (7)
H12C	0.6567	1.0756	0.0638	0.081*	0.256 (7)
H12D	0.7358	0.9814	0.1243	0.081*	0.256 (7)
C13A	0.6932 (7)	0.7918 (14)	0.0331 (4)	0.102 (3)	0.744 (7)
H13A	0.7545	0.7043	0.0384	0.123*	0.744 (7)
H13B	0.6718	0.8368	−0.0122	0.123*	0.744 (7)
C14A	0.6070 (3)	0.6572 (8)	0.0496 (3)	0.164 (3)	0.744 (7)
H14A	0.6042	0.5194	0.0290	0.245*	0.744 (7)
H14B	0.5423	0.7291	0.0340	0.245*	0.744 (7)
H14C	0.6209	0.6390	0.0961	0.245*	0.744 (7)
C13B	0.6925 (14)	0.770 (4)	0.0589 (11)	0.082 (6)	0.256 (7)
H13C	0.6474	0.7109	0.0839	0.098*	0.256 (7)
H13D	0.7538	0.6814	0.0658	0.098*	0.256 (7)
C14B	0.6399 (10)	0.782 (2)	−0.0107 (6)	0.111 (5)	0.256 (7)
H14D	0.6068	0.6475	−0.0247	0.166*	0.256 (7)
H14E	0.6892	0.8125	−0.0354	0.166*	0.256 (7)
H14F	0.5892	0.8937	−0.0175	0.166*	0.256 (7)
C15	1.49528 (18)	1.0890 (5)	0.16902 (14)	0.1059 (9)
H15A	1.4908	1.2311	0.1855	0.159*
H15B	1.4921	1.0958	0.1232	0.159*
H15C	1.5592	1.0247	0.1919	0.159*
H1N5	0.8984 (13)	1.445 (3)	−0.0018 (8)	0.053 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.04646 (19)	0.0376 (2)	0.04930 (19)	−0.00191 (14)	0.01724 (14)	0.00811 (15)
O1	0.0733 (7)	0.0373 (6)	0.0597 (6)	0.0047 (5)	0.0290 (5)	0.0156 (5)
O2	0.0634 (7)	0.0455 (6)	0.0582 (6)	−0.0161 (5)	0.0295 (5)	−0.0057 (5)
N1	0.0470 (6)	0.0360 (6)	0.0430 (5)	0.0075 (5)	0.0159 (5)	0.0074 (5)
N2	0.0652 (8)	0.0450 (8)	0.0605 (7)	0.0138 (6)	0.0207 (6)	0.0192 (6)
N3	0.0436 (6)	0.0370 (6)	0.0467 (6)	0.0015 (5)	0.0143 (5)	0.0112 (5)
N4	0.0403 (5)	0.0317 (6)	0.0409 (5)	0.0015 (4)	0.0127 (4)	0.0046 (4)
N5	0.0514 (7)	0.0394 (7)	0.0548 (7)	0.0039 (6)	0.0128 (5)	0.0145 (6)
N6	0.0474 (7)	0.0497 (8)	0.0666 (8)	0.0070 (6)	0.0108 (6)	0.0151 (7)
C1	0.0542 (8)	0.0500 (10)	0.0791 (10)	0.0052 (7)	0.0286 (8)	−0.0071 (8)
C2	0.0557 (9)	0.0518 (10)	0.0933 (13)	−0.0060 (8)	0.0234 (9)	−0.0122 (10)
C3	0.0485 (9)	0.0806 (14)	0.0764 (11)	−0.0124 (9)	0.0203 (8)	−0.0046 (10)
C4	0.0672 (11)	0.1099 (19)	0.0830 (12)	−0.0267 (12)	0.0424 (10)	−0.0313 (13)
C5	0.0622 (10)	0.0821 (14)	0.0679 (10)	−0.0176 (10)	0.0293 (8)	−0.0269 (10)
C6	0.0396 (6)	0.0440 (8)	0.0494 (7)	0.0044 (6)	0.0115 (5)	0.0046 (6)
C7	0.0599 (8)	0.0309 (7)	0.0384 (6)	−0.0021 (6)	0.0234 (5)	−0.0015 (5)
C8	0.0436 (6)	0.0301 (6)	0.0379 (6)	0.0011 (5)	0.0161 (5)	0.0017 (5)
C9	0.0425 (6)	0.0309 (6)	0.0454 (6)	−0.0014 (5)	0.0167 (5)	0.0051 (5)
C10	0.0480 (7)	0.0305 (6)	0.0346 (5)	0.0000 (5)	0.0126 (5)	0.0005 (5)
C11	0.0424 (7)	0.0443 (8)	0.0555 (8)	0.0043 (6)	0.0119 (6)	0.0050 (7)
C12	0.0438 (8)	0.0637 (12)	0.0984 (13)	0.0038 (8)	0.0222 (8)	0.0150 (11)
C13A	0.079 (3)	0.067 (4)	0.172 (8)	−0.012 (3)	0.054 (5)	−0.010 (4)
C14A	0.109 (3)	0.099 (3)	0.316 (8)	−0.047 (3)	0.115 (4)	−0.049 (4)
C13B	0.045 (5)	0.052 (6)	0.137 (15)	−0.018 (4)	0.004 (7)	0.034 (9)
C14B	0.080 (7)	0.132 (11)	0.102 (8)	−0.029 (7)	−0.013 (6)	0.001 (7)
C15	0.0746 (14)	0.125 (2)	0.130 (2)	−0.0437 (15)	0.0464 (14)	−0.0228 (18)

S1—C10	1.6805 (14)	C7—C8	1.4260 (18)
O1—N2	1.3698 (18)	C8—C9	1.4273 (18)
O1—C7	1.4118 (18)	C9—H9A	0.9300
O2—C7	1.1982 (17)	C11—C12	1.486 (2)
N1—N2	1.3051 (17)	C12—C13B	1.45 (2)
N1—C8	1.3515 (17)	C12—C13A	1.530 (10)
N1—C6	1.4482 (18)	C12—H12A	0.9600
N3—C9	1.2669 (17)	C12—H12B	0.9600
N3—N4	1.3838 (16)	C12—H12C	0.9700
N4—C11	1.3800 (17)	C12—H12D	0.9700
N4—C10	1.3806 (16)	C13A—C14A	1.539 (8)
N5—C10	1.3355 (19)	C13A—H13A	0.9700
N5—N6	1.3720 (18)	C13A—H13B	0.9700
N5—H1N5	0.855 (18)	C14A—H14A	0.9600
N6—C11	1.296 (2)	C14A—H14B	0.9600
C1—C6	1.373 (2)	C14A—H14C	0.9600
C1—C2	1.381 (2)	C13B—C14B	1.46 (2)
C1—H1A	0.9300	C13B—H13C	0.9700
C2—C3	1.374 (3)	C13B—H13D	0.9700
C2—H2A	0.9300	C14B—H14D	0.9600
C3—C4	1.384 (3)	C14B—H14E	0.9600
C3—C15	1.520 (3)	C14B—H14F	0.9600
C4—C5	1.381 (3)	C15—H15A	0.9600
C4—H4A	0.9300	C15—H15B	0.9600
C5—C6	1.372 (2)	C15—H15C	0.9600
C5—H5A	0.9300
N2—O1—C7	111.44 (10)	N6—C11—C12	125.49 (14)
N2—N1—C8	115.36 (12)	N4—C11—C12	123.46 (14)
N2—N1—C6	118.51 (12)	C13B—C12—C11	124.6 (8)
C8—N1—C6	126.06 (12)	C11—C12—C13A	108.9 (3)
N1—N2—O1	104.38 (11)	C13B—C12—H12A	113.0
C9—N3—N4	118.50 (11)	C11—C12—H12A	109.8
C11—N4—C10	108.14 (11)	C13A—C12—H12A	111.1
C11—N4—N3	118.55 (11)	C13B—C12—H12B	88.6
C10—N4—N3	133.28 (11)	C11—C12—H12B	109.7
C10—N5—N6	114.54 (13)	C13A—C12—H12B	109.0
C10—N5—H1N5	125.4 (12)	H12A—C12—H12B	108.4
N6—N5—H1N5	120.0 (12)	C13B—C12—H12C	108.4
C11—N6—N5	103.75 (12)	C11—C12—H12C	107.0
C6—C1—C2	118.49 (15)	C13A—C12—H12C	103.1
C6—C1—H1A	120.8	H12B—C12—H12C	118.7
C2—C1—H1A	120.8	C13B—C12—H12D	101.6
C3—C2—C1	121.25 (18)	C11—C12—H12D	107.3
C3—C2—H2A	119.4	C13A—C12—H12D	122.7
C1—C2—H2A	119.4	H12A—C12—H12D	96.0
C2—C3—C4	118.55 (17)	H12C—C12—H12D	106.8
C2—C3—C15	120.6 (2)	C12—C13A—C14A	111.7 (6)
C4—C3—C15	120.82 (18)	C12—C13A—H13A	109.3
C5—C4—C3	121.52 (17)	C14A—C13A—H13A	109.3
C5—C4—H4A	119.2	C12—C13A—H13B	109.3
C3—C4—H4A	119.2	C14A—C13A—H13B	109.3
C6—C5—C4	118.02 (18)	H13A—C13A—H13B	107.9
C6—C5—H5A	121.0	C12—C13B—C14B	103.8 (12)
C4—C5—H5A	121.0	C12—C13B—H13C	111.0
C5—C6—C1	122.16 (15)	C14B—C13B—H13C	111.0
C5—C6—N1	118.00 (14)	C12—C13B—H13D	111.0
C1—C6—N1	119.76 (13)	C14B—C13B—H13D	111.0
O2—C7—O1	120.32 (12)	H13C—C13B—H13D	109.0
O2—C7—C8	136.30 (14)	C13B—C14B—H14D	109.5
O1—C7—C8	103.37 (12)	C13B—C14B—H14E	109.5
N1—C8—C7	105.45 (12)	H14D—C14B—H14E	109.5
N1—C8—C9	121.96 (12)	C13B—C14B—H14F	109.5
C7—C8—C9	132.54 (12)	H14D—C14B—H14F	109.5
N3—C9—C8	119.54 (12)	H14E—C14B—H14F	109.5
N3—C9—H9A	120.2	C3—C15—H15A	109.5
C8—C9—H9A	120.2	C3—C15—H15B	109.5
N5—C10—N4	102.51 (12)	H15A—C15—H15B	109.5
N5—C10—S1	126.47 (11)	C3—C15—H15C	109.5
N4—C10—S1	131.01 (10)	H15A—C15—H15C	109.5
N6—C11—N4	111.05 (13)	H15B—C15—H15C	109.5
C8—N1—N2—O1	0.29 (16)	O1—C7—C8—N1	0.69 (13)
C6—N1—N2—O1	−176.84 (11)	O2—C7—C8—C9	−1.1 (3)
C7—O1—N2—N1	0.21 (15)	O1—C7—C8—C9	177.93 (13)
C9—N3—N4—C11	−175.21 (13)	N4—N3—C9—C8	−178.92 (11)
C9—N3—N4—C10	7.3 (2)	N1—C8—C9—N3	−177.96 (12)
C10—N5—N6—C11	−0.05 (18)	C7—C8—C9—N3	5.2 (2)
C6—C1—C2—C3	0.1 (3)	N6—N5—C10—N4	0.44 (16)
C1—C2—C3—C4	−0.4 (3)	N6—N5—C10—S1	−179.18 (11)
C1—C2—C3—C15	179.3 (2)	C11—N4—C10—N5	−0.64 (14)
C2—C3—C4—C5	0.9 (3)	N3—N4—C10—N5	177.05 (13)
C15—C3—C4—C5	−178.8 (2)	C11—N4—C10—S1	178.95 (11)
C3—C4—C5—C6	−1.0 (3)	N3—N4—C10—S1	−3.4 (2)
C4—C5—C6—C1	0.7 (3)	N5—N6—C11—N4	−0.38 (17)
C4—C5—C6—N1	177.43 (18)	N5—N6—C11—C12	179.64 (16)
C2—C1—C6—C5	−0.2 (3)	C10—N4—C11—N6	0.68 (17)
C2—C1—C6—N1	−176.94 (15)	N3—N4—C11—N6	−177.41 (12)
N2—N1—C6—C5	73.94 (19)	C10—N4—C11—C12	−179.35 (15)
C8—N1—C6—C5	−102.85 (18)	N3—N4—C11—C12	2.6 (2)
N2—N1—C6—C1	−109.20 (17)	N6—C11—C12—C13B	116.8 (9)
C8—N1—C6—C1	74.02 (19)	N4—C11—C12—C13B	−63.2 (9)
N2—O1—C7—O2	178.68 (12)	N6—C11—C12—C13A	100.0 (4)
N2—O1—C7—C8	−0.57 (14)	N4—C11—C12—C13A	−80.0 (4)
N2—N1—C8—C7	−0.65 (15)	C13B—C12—C13A—C14A	40 (2)
C6—N1—C8—C7	176.23 (12)	C11—C12—C13A—C14A	179.8 (5)
N2—N1—C8—C9	−178.25 (12)	C11—C12—C13B—C14B	−74.1 (13)
C6—N1—C8—C9	−1.4 (2)	C13A—C12—C13B—C14B	−26 (2)
O2—C7—C8—N1	−178.37 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H1N5···S1i	0.857 (18)	2.440 (18)	3.2933 (13)	174.3 (16)
C1—H1A···O2ii	0.93	2.48	3.346 (2)	154
C9—H9A···S1	0.93	2.42	3.1845 (13)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H1N5⋯S1i	0.857 (18)	2.440 (18)	3.2933 (13)	174.3 (16)
C1—H1A⋯O2ii	0.93	2.48	3.346 (2)	154
C9—H9A⋯S1	0.93	2.42	3.1845 (13)	139

Symmetry codes: (i) ; (ii) .