4-(2-{[4-Amino-6-(4-nitro­benz­yl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfan­yl}acet­yl)-3-phenyl­sydnone

Fun, H.-K.; Rosli, M.M.; Nithinchandra; Kalluraya, B.

doi:10.1107/S1600536811014504

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1196

doi:10.1107/S1600536811014504

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4-(2-{[4-Amino-6-(4-nitrobenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfanyl}acetyl)-3-phenylsydnone

Hoong-Kun Fun,^a ^*‡ Mohd Mustaqim Rosli,^a Nithinchandra ^b and Balakrishna Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 12 April 2011; accepted 18 April 2011; online 22 April 2011)

In the crystal, C₂₀H₁₅N₇O₆S, 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, molecules 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 intermolecular C—H⋯O interactions 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_r = 481.45
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.04
7793 reflections
315 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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⋯O3^iv	0.97	2.53	3.4443 (18)	157
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y, z; (iii) x+1, y, z-1; (iv) -x+2, -y+2, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014504/is2702sup1.cif

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

checkCIF report

Comment top

Sydnones are mesoionic heterocyclic aromatic compounds. The study of sydnones still remains a field of interest because of their electronic structures and also because of the varied types of biological activities displayed by some of them (Rai et al., 2008). Recently sydnone derivatives were found to exhibit promising antimicrobial properties (Kalluraya et al., 2008). Since their discovery, sydnones have shown diverse biological activities and it is thought that the meso-ionic nature of the sydnone ring promotes significant interactions with biological systems. Because of wide variety of properties displayed by sydnones ,we were prompted to synthesize a new S-substituted triazinones containing a sydnone ring.

Photochemical bromination of 3-aryl-4-acetylsydnone afforded 3-aryl-4 bromoacetylsydnones. Condensation of 4-amino-6-(p-nitrobenzyl)-3-sulfanyl-1,2,4-triazin-5(4H)-one with 3-phenyl-4-bromoacetylsydnones yielded S-substituted triazinone derivatives (Jyothi et al., 2008).

All parameters in (I), Fig. 1, are within normal ranges and comparable with the related structure (Fun et al., 2011). The dihedral angle between oxadiazole (C7/C8/N1/N2/O1) and triazine (C11/N3/C12/C13/N4/N5) groups is 86.94 (7)°. The oxadiazole and triazine groups make dihedral angles of 52.96 (8) and 83.08 (7)° with the C1–C6 phneyl ring and 9.51 (8) and 82.08 (7)° with the C15–C20 benzene ring, respectively.

In the crystal structure, the N7—H2N7···O4ⁱ, N7—H1N7···N4ⁱⁱ, N7—H1N7···N5ⁱⁱ, C3—H3A···O5ⁱⁱⁱ and C14—H14A···O3^iv intermolecular interactions (Table 1) link the molecules into two-dimensional sheets parallel to the ac-plane (Fig. 2).

Related literature top

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

Experimental top

To a solution of 4-bromoacetyl-3-phenylsydnone (0.01mol) and 4-amino-6-(p-nitrobenzyl)-3-sulfanyl-1,2,4-triazin-5(4H)-one (0.01mol) in ethanol, a catalytic amount of anhydrous sodium acetate was added. The solution was stirred at room temperature for 2-3 hours. The solid product that separated out was filtered and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from 1:2 mixtures of DMF and ethanol by slow evaporation.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal packing of (I) viewed along the a axis. Dashed lines indicate hydrogen bonds. H atoms not involved in the hydrogen bond interactions have been omitted for clarity.

4-(2-{[4-Amino-6-(4-nitrobenzyl)-5-oxo-4,5-dihydro-1,2,4- triazin-3-yl]sulfanyl}acetyl)-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate top

Crystal data top

C₂₀H₁₅N₇O₆S	Z = 2
M_r = 481.45	F(000) = 496
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0615P)² + 0.084P] where P = (F_o² + 2F_c²)/3
7793 reflections	(Δ/σ)_max < 0.001
315 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₅N₇O₆S	γ = 97.551 (1)°
M_r = 481.45	V = 1058.61 (3) Å³
Triclinic, P1	Z = 2
a = 6.4071 (1) Å	Mo Kα radiation
b = 10.1629 (2) Å	µ = 0.21 mm⁻¹
c = 17.1521 (3) Å	T = 297 K
α = 106.372 (1)°	0.51 × 0.34 × 0.17 mm
β = 92.400 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	7793 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5330 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.965	R_int = 0.030
21821 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.25 e Å⁻³
7793 reflections	Δρ_min = −0.23 e Å⁻³
315 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.97	2.53	3.4443 (18)	157

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z; (iii) x+1, y, z−1; (iv) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅N₇O₆S
M_r	481.45
Crystal system, space group	Triclinic, P1
Temperature (K)	297
a, b, c (Å)	6.4071 (1), 10.1629 (2), 17.1521 (3)
α, β, γ (°)	106.372 (1), 92.400 (1), 97.551 (1)
V (Å³)	1058.61 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.51 × 0.34 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.900, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	21821, 7793, 5330
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.763

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.131, 1.04
No. of reflections	7793
No. of parameters	315
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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	0.9300	2.5700	3.345 (3)	141.00
C14—H14A···O3^iv	0.9700	2.5300	3.4443 (18)	157.00

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z; (iii) x+1, y, z−1; (iv) −x+2, −y+2, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MMR thank USM for the Research University Grant (No. 1001/PFIZIK/811160).

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Quah, C. K., Nithinchandra, & Kalluraya, B. (2011). Acta Cryst. E67, o1004. Google Scholar
Jyothi, C. H., Girisha, K. S., Adithya, A. & Kalluraya, B. (2008). Eur. J. Med. Chem. 43, 2831–2834. Web of Science PubMed Google Scholar
Kalluraya, B., Nayak, J., Adhikari, A., Sujith, K. V., Shetty, N. S. & Winter, M. (2008a). Phosphorus Sulfur Silicon Relat. Elem. 183, 1870–1883. CrossRef CAS Google Scholar
Kalluraya, B., Rao, J. N. & Sujith, K. V. (2008b). Indian J. Heterocycl. Chem. 17, 359–362. CAS Google Scholar
Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem. 43, 1715–1720. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Page o1196

doi:10.1107/S1600536811014504

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-(2-{[4-Amino-6-(4-nitro­benz­yl)-5-oxo-4,5-di­hydro-1,2,4-triazin-3-yl]sulfan­yl}acet­yl)-3-phenyl­sydnone

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Experimental

Crystal data

Data collection

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Supporting information

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References

organic compounds

4-(2-{[4-Amino-6-(4-nitrobenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-3-yl]sulfanyl}acetyl)-3-phenylsydnone