4-(2-{[4-Amino-6-(4-nitro-benz-yl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan-yl}acet-yl)-3-phenyl-sydnone.

In the crystal, C(20)H(15)N(7)O(6)S, the dihedral angle between the oxadiazole and triazine rings is 86.94 (7)°. The oxadiazole ring makes a dihedral angle of 52.96 (8)° with the phenyl ring, while the triazine ring makes a dihedral angle of 82.08 (7)° with the benzene ring. In the structure, mol-ecules are linked by a pair of N-H⋯O hydrogen bonds, forming an inversion dimer. The dimers are further stacked along the a axis via N-H⋯N hydrogen bonds. Weak inter-molecular C-H⋯O inter-actions are also observed.

Related literature

For the biological activity of sydnone derivatives, see: Rai et al. (2008 ▶); Jyothi et al. (2008 ▶); Kalluraya et al. (2008a ▶,b ▶). For a related structure, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C20H15N7O6S

M = 481.45

Triclinic,

a = 6.4071 (1) Å

b = 10.1629 (2) Å

c = 17.1521 (3) Å

α = 106.372 (1)°

β = 92.400 (1)°

γ = 97.551 (1)°

V = 1058.61 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 297 K

0.51 × 0.34 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.900, T max = 0.965

21821 measured reflections

7793 independent reflections

5330 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.131

S = 1.04

7793 reflections

315 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.23 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 datablocks global, I. DOI: 10.1107/S1600536811014504/is2702sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014504/is2702Isup2.hkl

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

C20H15N7O6S	Z = 2
Mr = 481.45	F(000) = 496
Triclinic, P1	Dx = 1.510 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4071 (1) Å	Cell parameters from 5430 reflections
b = 10.1629 (2) Å	θ = 3.7–30.1°
c = 17.1521 (3) Å	µ = 0.21 mm−1
α = 106.372 (1)°	T = 297 K
β = 92.400 (1)°	Block, yellow
γ = 97.551 (1)°	0.51 × 0.34 × 0.17 mm
V = 1058.61 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	7793 independent reflections
Radiation source: fine-focus sealed tube	5330 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 32.8°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.900, Tmax = 0.965	k = −15→15
21821 measured reflections	l = −26→26

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0615P)2 + 0.084P] where P = (Fo2 + 2Fc2)/3
7793 reflections	(Δ/σ)max < 0.001
315 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 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	0.76158 (5)	0.56912 (4)	0.39458 (2)	0.04815 (10)
N1	1.40303 (17)	0.45428 (11)	0.21692 (6)	0.0388 (2)
N2	1.5454 (2)	0.37194 (13)	0.20533 (8)	0.0525 (3)
N3	0.73930 (15)	0.81262 (11)	0.49757 (6)	0.0362 (2)
N4	1.14452 (17)	0.85392 (13)	0.56156 (7)	0.0460 (3)
N5	1.06998 (16)	0.73678 (12)	0.49822 (7)	0.0430 (2)
N6	0.8522 (4)	0.87248 (18)	0.93514 (10)	0.0851 (6)
N7	0.52842 (19)	0.77429 (15)	0.46377 (9)	0.0531 (3)
O1	1.51411 (17)	0.29797 (10)	0.26042 (7)	0.0531 (3)
O2	1.29331 (18)	0.28459 (11)	0.35900 (7)	0.0565 (3)
O3	1.07909 (19)	0.62369 (11)	0.28170 (7)	0.0604 (3)
O4	0.68160 (17)	1.01247 (11)	0.58890 (6)	0.0536 (3)
O5	0.6980 (4)	0.9118 (2)	0.96790 (12)	0.1335 (8)
O6	0.9522 (4)	0.7945 (2)	0.95653 (11)	0.1279 (8)
C1	1.2266 (3)	0.54038 (16)	0.11647 (9)	0.0520 (3)
H1A	1.1003	0.4875	0.1210	0.062*
C2	1.2384 (3)	0.61847 (18)	0.06204 (10)	0.0643 (4)
H2A	1.1181	0.6198	0.0302	0.077*
C3	1.4275 (3)	0.69420 (17)	0.05489 (10)	0.0653 (5)
H3A	1.4347	0.7444	0.0171	0.078*
C4	1.6052 (3)	0.69646 (18)	0.10286 (11)	0.0660 (4)
H4A	1.7315	0.7491	0.0980	0.079*
C5	1.5974 (3)	0.62030 (16)	0.15882 (10)	0.0541 (3)
H5A	1.7166	0.6213	0.1919	0.065*
C6	1.4068 (2)	0.54316 (13)	0.16354 (7)	0.0412 (3)
C7	1.3425 (2)	0.33732 (13)	0.30715 (8)	0.0411 (3)
C8	1.27298 (19)	0.44150 (12)	0.27599 (7)	0.0352 (2)
C9	1.1124 (2)	0.52770 (12)	0.30653 (7)	0.0382 (2)
C10	0.9904 (2)	0.48508 (14)	0.37157 (8)	0.0438 (3)
H10A	1.0834	0.5066	0.4210	0.053*
H10B	0.9464	0.3855	0.3535	0.053*
C11	0.87411 (17)	0.71923 (13)	0.47012 (7)	0.0347 (2)
C12	0.8018 (2)	0.93081 (13)	0.56189 (7)	0.0380 (2)
C13	1.0230 (2)	0.94417 (13)	0.59158 (7)	0.0392 (3)
C14	1.1084 (2)	1.06316 (14)	0.66524 (8)	0.0484 (3)
H14A	1.0497	1.1456	0.6635	0.058*
H14B	1.2609	1.0831	0.6662	0.058*
C15	1.0474 (2)	1.02257 (13)	0.74039 (8)	0.0418 (3)
C16	0.8680 (3)	1.05963 (15)	0.77747 (9)	0.0516 (3)
H16A	0.7898	1.1176	0.7592	0.062*
C17	0.8036 (3)	1.01111 (17)	0.84163 (10)	0.0592 (4)
H17A	0.6821	1.0350	0.8663	0.071*
C18	0.9234 (3)	0.92666 (15)	0.86812 (9)	0.0575 (4)
C19	1.1038 (3)	0.89030 (17)	0.83385 (10)	0.0652 (5)
H19A	1.1834	0.8342	0.8533	0.078*
C20	1.1651 (3)	0.93889 (16)	0.76961 (9)	0.0559 (4)
H20A	1.2875	0.9151	0.7455	0.067*
H2N7	0.492 (3)	0.848 (2)	0.4511 (12)	0.084 (6)*
H1N7	0.456 (3)	0.764 (2)	0.5051 (13)	0.077 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.03577 (16)	0.0519 (2)	0.0551 (2)	0.01356 (13)	0.00911 (13)	0.00898 (15)
N1	0.0436 (5)	0.0376 (5)	0.0387 (5)	0.0140 (4)	0.0093 (4)	0.0123 (4)
N2	0.0569 (7)	0.0522 (7)	0.0586 (7)	0.0271 (5)	0.0224 (6)	0.0211 (6)
N3	0.0302 (4)	0.0467 (5)	0.0407 (5)	0.0173 (4)	0.0105 (4)	0.0210 (4)
N4	0.0339 (5)	0.0572 (7)	0.0483 (6)	0.0106 (5)	0.0098 (4)	0.0150 (5)
N5	0.0310 (5)	0.0536 (6)	0.0477 (6)	0.0155 (4)	0.0102 (4)	0.0147 (5)
N6	0.1383 (18)	0.0596 (9)	0.0504 (8)	−0.0176 (10)	0.0025 (10)	0.0201 (7)
N7	0.0326 (5)	0.0653 (8)	0.0628 (8)	0.0238 (5)	0.0036 (5)	0.0135 (6)
O1	0.0586 (6)	0.0485 (5)	0.0657 (6)	0.0301 (5)	0.0198 (5)	0.0259 (5)
O2	0.0658 (7)	0.0529 (6)	0.0680 (6)	0.0225 (5)	0.0167 (5)	0.0374 (5)
O3	0.0766 (7)	0.0571 (6)	0.0694 (7)	0.0392 (6)	0.0293 (6)	0.0371 (5)
O4	0.0598 (6)	0.0541 (6)	0.0554 (6)	0.0336 (5)	0.0097 (5)	0.0177 (5)
O5	0.181 (2)	0.1328 (17)	0.1005 (13)	0.0027 (15)	0.0624 (14)	0.0588 (12)
O6	0.212 (2)	0.1014 (12)	0.0919 (11)	0.0126 (13)	0.0041 (13)	0.0687 (11)
C1	0.0579 (8)	0.0514 (8)	0.0478 (7)	0.0030 (6)	−0.0001 (6)	0.0193 (6)
C2	0.0845 (12)	0.0638 (10)	0.0494 (8)	0.0089 (9)	−0.0052 (8)	0.0264 (7)
C3	0.0971 (14)	0.0556 (9)	0.0515 (8)	0.0105 (9)	0.0159 (9)	0.0280 (7)
C4	0.0753 (11)	0.0606 (10)	0.0676 (10)	0.0017 (8)	0.0239 (9)	0.0287 (8)
C5	0.0531 (8)	0.0571 (8)	0.0553 (8)	0.0070 (7)	0.0109 (6)	0.0209 (7)
C6	0.0510 (7)	0.0393 (6)	0.0364 (6)	0.0113 (5)	0.0102 (5)	0.0131 (5)
C7	0.0440 (6)	0.0350 (6)	0.0491 (7)	0.0139 (5)	0.0080 (5)	0.0157 (5)
C8	0.0373 (6)	0.0334 (5)	0.0390 (6)	0.0113 (4)	0.0073 (4)	0.0139 (4)
C9	0.0417 (6)	0.0365 (6)	0.0401 (6)	0.0141 (5)	0.0074 (5)	0.0126 (5)
C10	0.0462 (7)	0.0436 (7)	0.0486 (7)	0.0187 (5)	0.0152 (5)	0.0178 (5)
C11	0.0305 (5)	0.0442 (6)	0.0386 (5)	0.0149 (4)	0.0137 (4)	0.0211 (5)
C12	0.0436 (6)	0.0423 (6)	0.0388 (6)	0.0177 (5)	0.0119 (5)	0.0230 (5)
C13	0.0400 (6)	0.0438 (6)	0.0413 (6)	0.0083 (5)	0.0116 (5)	0.0221 (5)
C14	0.0534 (8)	0.0445 (7)	0.0499 (7)	0.0040 (6)	0.0077 (6)	0.0190 (6)
C15	0.0499 (7)	0.0350 (6)	0.0403 (6)	0.0085 (5)	0.0014 (5)	0.0102 (5)
C16	0.0597 (9)	0.0499 (8)	0.0527 (8)	0.0211 (6)	0.0097 (6)	0.0205 (6)
C17	0.0697 (10)	0.0567 (9)	0.0513 (8)	0.0109 (7)	0.0181 (7)	0.0132 (7)
C18	0.0912 (12)	0.0417 (7)	0.0373 (6)	−0.0004 (7)	0.0020 (7)	0.0130 (5)
C19	0.0953 (13)	0.0524 (8)	0.0544 (9)	0.0241 (9)	−0.0070 (9)	0.0219 (7)
C20	0.0632 (9)	0.0554 (8)	0.0547 (8)	0.0252 (7)	0.0043 (7)	0.0177 (7)

S1—C11	1.7448 (13)	C3—C4	1.370 (3)
S1—C10	1.7951 (13)	C3—H3A	0.9300
N1—N2	1.3013 (15)	C4—C5	1.391 (2)
N1—C8	1.3616 (15)	C4—H4A	0.9300
N1—C6	1.4550 (16)	C5—C6	1.380 (2)
N2—O1	1.3693 (15)	C5—H5A	0.9300
N3—C11	1.3660 (14)	C7—C8	1.4242 (16)
N3—C12	1.3820 (17)	C8—C9	1.4572 (16)
N3—N7	1.4079 (15)	C9—C10	1.5165 (17)
N4—C13	1.2914 (17)	C10—H10A	0.9700
N4—N5	1.3797 (16)	C10—H10B	0.9700
N5—C11	1.2966 (15)	C12—C13	1.4615 (18)
N6—O6	1.205 (3)	C13—C14	1.5049 (19)
N6—O5	1.214 (3)	C14—C15	1.5112 (18)
N6—C18	1.472 (2)	C14—H14A	0.9700
N7—H2N7	0.90 (2)	C14—H14B	0.9700
N7—H1N7	0.89 (2)	C15—C16	1.381 (2)
O1—C7	1.4212 (16)	C15—C20	1.3856 (19)
O2—C7	1.1937 (16)	C16—C17	1.384 (2)
O3—C9	1.2083 (15)	C16—H16A	0.9300
O4—C12	1.2156 (15)	C17—C18	1.377 (2)
C1—C6	1.373 (2)	C17—H17A	0.9300
C1—C2	1.384 (2)	C18—C19	1.366 (3)
C1—H1A	0.9300	C19—C20	1.380 (2)
C2—C3	1.377 (3)	C19—H19A	0.9300
C2—H2A	0.9300	C20—H20A	0.9300
C11—S1—C10	100.23 (6)	O3—C9—C10	123.28 (11)
N2—N1—C8	114.78 (10)	C8—C9—C10	113.88 (10)
N2—N1—C6	114.59 (10)	C9—C10—S1	113.41 (9)
C8—N1—C6	130.62 (10)	C9—C10—H10A	108.9
N1—N2—O1	105.29 (10)	S1—C10—H10A	108.9
C11—N3—C12	121.18 (10)	C9—C10—H10B	108.9
C11—N3—N7	116.60 (11)	S1—C10—H10B	108.9
C12—N3—N7	121.80 (10)	H10A—C10—H10B	107.7
C13—N4—N5	120.91 (11)	N5—C11—N3	123.75 (12)
C11—N5—N4	118.18 (11)	N5—C11—S1	121.37 (9)
O6—N6—O5	122.9 (2)	N3—C11—S1	114.86 (9)
O6—N6—C18	118.8 (2)	O4—C12—N3	122.00 (12)
O5—N6—C18	118.2 (2)	O4—C12—C13	125.50 (12)
N3—N7—H2N7	106.2 (14)	N3—C12—C13	112.50 (10)
N3—N7—H1N7	104.2 (14)	N4—C13—C12	123.40 (12)
H2N7—N7—H1N7	107.5 (19)	N4—C13—C14	118.21 (12)
N2—O1—C7	110.84 (9)	C12—C13—C14	118.20 (11)
C6—C1—C2	118.12 (15)	C13—C14—C15	108.09 (10)
C6—C1—H1A	120.9	C13—C14—H14A	110.1
C2—C1—H1A	120.9	C15—C14—H14A	110.1
C3—C2—C1	120.27 (16)	C13—C14—H14B	110.1
C3—C2—H2A	119.9	C15—C14—H14B	110.1
C1—C2—H2A	119.9	H14A—C14—H14B	108.4
C4—C3—C2	120.72 (14)	C16—C15—C20	119.09 (13)
C4—C3—H3A	119.6	C16—C15—C14	121.16 (12)
C2—C3—H3A	119.6	C20—C15—C14	119.60 (13)
C3—C4—C5	120.24 (16)	C15—C16—C17	120.48 (14)
C3—C4—H4A	119.9	C15—C16—H16A	119.8
C5—C4—H4A	119.9	C17—C16—H16A	119.8
C6—C5—C4	117.79 (16)	C18—C17—C16	118.61 (16)
C6—C5—H5A	121.1	C18—C17—H17A	120.7
C4—C5—H5A	121.1	C16—C17—H17A	120.7
C1—C6—C5	122.84 (13)	C19—C18—C17	122.36 (14)
C1—C6—N1	119.32 (12)	C19—C18—N6	119.06 (17)
C5—C6—N1	117.71 (13)	C17—C18—N6	118.58 (19)
O2—C7—O1	120.32 (11)	C18—C19—C20	118.29 (15)
O2—C7—C8	136.17 (13)	C18—C19—H19A	120.9
O1—C7—C8	103.50 (10)	C20—C19—H19A	120.9
N1—C8—C7	105.59 (10)	C19—C20—C15	121.14 (16)
N1—C8—C9	126.62 (10)	C19—C20—H20A	119.4
C7—C8—C9	127.47 (11)	C15—C20—H20A	119.4
O3—C9—C8	122.84 (12)
C8—N1—N2—O1	−0.65 (15)	C12—N3—C11—N5	−3.89 (17)
C6—N1—N2—O1	−179.61 (10)	N7—N3—C11—N5	−176.56 (12)
C13—N4—N5—C11	−0.56 (18)	C12—N3—C11—S1	174.64 (8)
N1—N2—O1—C7	0.50 (15)	N7—N3—C11—S1	1.97 (14)
C6—C1—C2—C3	1.2 (3)	C10—S1—C11—N5	−5.61 (11)
C1—C2—C3—C4	−1.7 (3)	C10—S1—C11—N3	175.82 (8)
C2—C3—C4—C5	0.9 (3)	C11—N3—C12—O4	−177.39 (11)
C3—C4—C5—C6	0.4 (3)	N7—N3—C12—O4	−5.09 (18)
C2—C1—C6—C5	0.1 (2)	C11—N3—C12—C13	2.88 (15)
C2—C1—C6—N1	−175.51 (14)	N7—N3—C12—C13	175.17 (11)
C4—C5—C6—C1	−0.9 (2)	N5—N4—C13—C12	−0.10 (18)
C4—C5—C6—N1	174.80 (13)	N5—N4—C13—C14	174.79 (11)
N2—N1—C6—C1	124.32 (14)	O4—C12—C13—N4	179.22 (12)
C8—N1—C6—C1	−54.43 (19)	N3—C12—C13—N4	−1.05 (16)
N2—N1—C6—C5	−51.51 (17)	O4—C12—C13—C14	4.33 (18)
C8—N1—C6—C5	129.74 (15)	N3—C12—C13—C14	−175.94 (10)
N2—O1—C7—O2	−179.23 (13)	N4—C13—C14—C15	−92.98 (14)
N2—O1—C7—C8	−0.19 (14)	C12—C13—C14—C15	82.18 (14)
N2—N1—C8—C7	0.54 (15)	C13—C14—C15—C16	−94.98 (15)
C6—N1—C8—C7	179.29 (12)	C13—C14—C15—C20	80.63 (16)
N2—N1—C8—C9	174.43 (12)	C20—C15—C16—C17	−1.6 (2)
C6—N1—C8—C9	−6.8 (2)	C14—C15—C16—C17	174.06 (13)
O2—C7—C8—N1	178.62 (16)	C15—C16—C17—C18	0.7 (2)
O1—C7—C8—N1	−0.19 (13)	C16—C17—C18—C19	0.6 (2)
O2—C7—C8—C9	4.8 (3)	C16—C17—C18—N6	−178.61 (14)
O1—C7—C8—C9	−174.00 (12)	O6—N6—C18—C19	−1.9 (3)
N1—C8—C9—O3	−0.7 (2)	O5—N6—C18—C19	176.04 (19)
C7—C8—C9—O3	171.92 (13)	O6—N6—C18—C17	177.31 (17)
N1—C8—C9—C10	178.87 (12)	O5—N6—C18—C17	−4.7 (3)
C7—C8—C9—C10	−8.56 (19)	C17—C18—C19—C20	−1.0 (3)
O3—C9—C10—S1	10.82 (18)	N6—C18—C19—C20	178.23 (14)
C8—C9—C10—S1	−168.69 (9)	C18—C19—C20—C15	0.1 (2)
C11—S1—C10—C9	−88.06 (10)	C16—C15—C20—C19	1.2 (2)
N4—N5—C11—N3	2.54 (18)	C14—C15—C20—C19	−174.51 (14)
N4—N5—C11—S1	−175.89 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H2N7···O4i	0.89 (2)	2.15 (2)	3.0152 (19)	163.5 (18)
N7—H1N7···N4ii	0.89 (2)	2.43 (2)	3.1019 (17)	133.1 (17)
N7—H1N7···N5ii	0.89 (2)	2.45 (2)	3.0166 (16)	122.5 (16)
C3—H3A···O5iii	0.93	2.57	3.345 (3)	141.
C14—H14A···O3iv	0.97	2.53	3.4443 (18)	157.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H2N7⋯O4i	0.89 (2)	2.15 (2)	3.0152 (19)	163.5 (18)
N7—H1N7⋯N4ii	0.89 (2)	2.43 (2)	3.1019 (17)	133.1 (17)
N7—H1N7⋯N5ii	0.89 (2)	2.45 (2)	3.0166 (16)	122.5 (16)
C3—H3A⋯O5iii	0.93	2.57	3.345 (3)	141
C14—H14A⋯O3iv	0.97	2.53	3.4443 (18)	157

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