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

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

doi:10.1107/S1600536811007689

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o820

doi:10.1107/S1600536811007689

Open

access

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

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^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 28 February 2011; accepted 1 March 2011; online 9 March 2011)

In the title syndone (1,2,3-oxadiazol-3-ylium-5-olate) compound, C₂₁H₁₆ClN₅O₄S, the dihedral angle between the benzene and oxadiazole rings is 55.62 (11)° and that between the triazine and the chloro-substituted phenyl rings is 82.45 (9)°. There is an intramolecular C—H⋯S hydrogen bond, which generates an S(5) ring motif. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R₂²(20) loops. The dimers are connected by C—H⋯N and C—H⋯O hydrogen bonds.

Related literature

For applications of sydnones, see: Rai et al. (2008 ); Jyothi et al. (2008 ).

Experimental

Crystal data

C₂₁H₁₆ClN₅O₄S
M_r = 469.90
Triclinic, $[P \overline 1]$
a = 6.4604 (1) Å
b = 10.1634 (2) Å
c = 16.9901 (4) Å
α = 105.264 (1)°
β = 92.103 (1)°
γ = 97.363 (1)°
V = 1064.44 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 296 K
0.62 × 0.39 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.828, T_max = 0.959
21841 measured reflections
6389 independent reflections
4781 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.154
S = 1.05
6389 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O2ⁱ	0.97	2.52	3.429 (3)	157
C11—H11A⋯S1	0.96	2.12	2.7577 (17)	122
C11—H11B⋯N1ⁱⁱ	0.96	2.36	3.066 (2)	130
C11—H11B⋯N2ⁱⁱ	0.96	2.40	3.0304 (19)	123
C11—H11C⋯O1ⁱⁱⁱ	0.96	2.07	3.021 (2)	169
Symmetry codes: (i) -x+1, -y, -z; (ii) x+1, y, z; (iii) -x+2, -y, -z.

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/S1600536811007689/hb5811sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007689/hb5811Isup2.hkl

checkCIF report

Comment top

Sydnones (1,2,3-oxadiazol-3-ylium-5-olates) 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 being reported (Rai et al., 2008). Recently sydnone derivatives were found to exhibit promising anti-microbial properties (Jyothi 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. Photochemical bromination of 3-aryl-4-acetylsydnone afforded 3-aryl-4 bromoacetylsydnones. Condensation of 6-(4-chlorobenzyl)-4-methyl-3- sulfanyl-1,2,4-triazin-5(4H)-one with 3-aryl-4-bromoacetylsydnones yielded S-substituted triazinone derivatives (Jyothi et al., 2008).

In the title compound (Fig. 1), the rings A (C16–C21), B (N4/N5/O4/C14–C15), C (N1/N2/N3/C8–C10) and D (C1–C6) are essentially planar. The dihedral angle between the best planes of the rings are A/B = 55.62 (11)°, A/C = 83.22 (10)°, A/D = 49.75 (11)°, B/C = 87.81 (9)°, B/D = 8.97 (10)° and C/D = 82.45 (9)°.

In the crystal (Fig. 2), symmetry-related molecules are linked into centrosymmetic dimers via pairs of intermolecular C—H···O hydrogen bonds, generating an R²₂(20) ring. Furthermore, these dimers are connected via C—H···N and C—H···O hydrogen bonds. There is an intramolecular C—H···S hydrogen bond, which generates an S(5) ring motif.

Related literature top

For applications of sydnones, see: Rai et al. (2008); Jyothi et al. (2008).

Experimental top

To a mixture of 4-bromoacetyl-3-phenylsydnone (0.01 mol) and 6-(4-chlorobenzyl)-4-methyl-3-sulfanyl-1,2,4-triazin-5(4H)-one (0.01 mol) in ethanol, a catalytic amount of anhydrous sodium acetate was added. The solution was stirred at room temperature for 2-3hours. The solid product separated was filtered and dried. It was then recrystallized from ethanol. Colourless plates of (I) 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 asymmetric unit of the title compound, showing 30% probability displacement ellipsoids. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of the title compound (I).

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

Crystal data top

C₂₁H₁₆ClN₅O₄S	Z = 2
M_r = 469.90	F(000) = 484
Triclinic, P1	D_x = 1.466 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4604 (1) Å	Cell parameters from 9469 reflections
b = 10.1634 (2) Å	θ = 2.5–30.3°
c = 16.9901 (4) Å	µ = 0.32 mm⁻¹
α = 105.264 (1)°	T = 296 K
β = 92.103 (1)°	Plate, colourless
γ = 97.363 (1)°	0.62 × 0.39 × 0.13 mm
V = 1064.44 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6389 independent reflections
Radiation source: fine-focus sealed tube	4781 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 30.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
T_min = 0.828, T_max = 0.959	k = −14→14
21841 measured reflections	l = −24→23

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0757P)² + 0.3213P] where P = (F_o² + 2F_c²)/3
6389 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₁H₁₆ClN₅O₄S	γ = 97.363 (1)°
M_r = 469.90	V = 1064.44 (4) Å³
Triclinic, P1	Z = 2
a = 6.4604 (1) Å	Mo Kα radiation
b = 10.1634 (2) Å	µ = 0.32 mm⁻¹
c = 16.9901 (4) Å	T = 296 K
α = 105.264 (1)°	0.62 × 0.39 × 0.13 mm
β = 92.103 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6389 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4781 reflections with I > 2σ(I)
T_min = 0.828, T_max = 0.959	R_int = 0.020
21841 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.05	Δρ_max = 0.63 e Å⁻³
6389 reflections	Δρ_min = −0.49 e Å⁻³
290 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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
Cl1	0.62801 (16)	0.17208 (7)	−0.44701 (4)	0.0927 (3)
S1	0.74666 (7)	0.42674 (5)	0.10616 (3)	0.04942 (14)
O1	0.8261 (2)	−0.00776 (14)	−0.09214 (9)	0.0536 (3)
O2	0.4372 (2)	0.37342 (15)	0.22327 (10)	0.0631 (4)
O3	0.2131 (2)	0.70857 (15)	0.14094 (9)	0.0569 (4)
O4	−0.0096 (2)	0.68960 (14)	0.23895 (9)	0.0525 (3)
N1	0.3637 (2)	0.14727 (17)	−0.05789 (10)	0.0455 (3)
N2	0.4389 (2)	0.26204 (16)	0.00528 (9)	0.0432 (3)
N3	0.76804 (19)	0.18731 (14)	0.00212 (8)	0.0357 (3)
N4	−0.0422 (3)	0.61324 (17)	0.29404 (10)	0.0513 (4)
N5	0.1021 (2)	0.53269 (14)	0.28321 (9)	0.0391 (3)
C1	0.6273 (3)	−0.0406 (2)	−0.28017 (12)	0.0538 (5)
H1A	0.7109	−0.0981	−0.2639	0.065*
C2	0.6816 (4)	0.0139 (2)	−0.34463 (13)	0.0614 (5)
H2A	0.8010	−0.0068	−0.3715	0.074*
C3	0.5567 (4)	0.0987 (2)	−0.36822 (12)	0.0573 (5)
C4	0.3787 (4)	0.1282 (2)	−0.33058 (13)	0.0625 (6)
H4A	0.2938	0.1839	−0.3481	0.075*
C5	0.3265 (4)	0.0743 (2)	−0.26612 (13)	0.0559 (5)
H5A	0.2063	0.0950	−0.2398	0.067*
C6	0.4501 (3)	−0.01022 (17)	−0.23998 (11)	0.0429 (4)
C7	0.3994 (3)	−0.05628 (19)	−0.16429 (12)	0.0491 (4)
H7A	0.2491	−0.0782	−0.1632	0.059*
H7B	0.4621	−0.1381	−0.1645	0.059*
C8	0.4848 (3)	0.05888 (18)	−0.09049 (10)	0.0391 (3)
C9	0.7063 (3)	0.07191 (17)	−0.06296 (10)	0.0381 (3)
C10	0.6336 (2)	0.27910 (17)	0.03115 (10)	0.0351 (3)
C11	0.9776 (2)	0.22301 (18)	0.03403 (11)	0.0415 (4)
H11A	0.9900	0.3032	0.0799	0.062*
H11B	1.0642	0.2424	−0.0074	0.062*
H11C	1.0218	0.1478	0.0515	0.062*
C12	0.5200 (3)	0.51093 (19)	0.13034 (12)	0.0451 (4)
H12A	0.5638	0.6097	0.1483	0.054*
H12B	0.4277	0.4916	0.0811	0.054*
C13	0.3992 (3)	0.46689 (17)	0.19597 (10)	0.0396 (3)
C14	0.2332 (2)	0.54916 (16)	0.22475 (10)	0.0364 (3)
C15	0.1633 (3)	0.65315 (17)	0.19282 (11)	0.0421 (4)
C16	0.0970 (3)	0.44216 (18)	0.33652 (10)	0.0433 (4)
C17	0.2718 (4)	0.4479 (2)	0.38688 (13)	0.0567 (5)
H17A	0.3960	0.5035	0.3843	0.068*
C18	0.2562 (5)	0.3678 (3)	0.44141 (15)	0.0719 (7)
H18A	0.3719	0.3693	0.4760	0.086*
C19	0.0713 (5)	0.2859 (3)	0.44518 (15)	0.0728 (7)
H19A	0.0623	0.2345	0.4832	0.087*
C20	−0.1000 (5)	0.2797 (3)	0.39297 (16)	0.0711 (6)
H20A	−0.2230	0.2223	0.3947	0.085*
C21	−0.0893 (3)	0.3590 (2)	0.33778 (13)	0.0568 (5)
H21A	−0.2043	0.3564	0.3026	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1528 (8)	0.0725 (4)	0.0568 (4)	0.0023 (4)	0.0182 (4)	0.0294 (3)
S1	0.0344 (2)	0.0530 (3)	0.0574 (3)	0.01232 (18)	0.00630 (18)	0.0057 (2)
O1	0.0572 (8)	0.0531 (8)	0.0570 (8)	0.0312 (6)	0.0076 (6)	0.0144 (6)
O2	0.0748 (10)	0.0590 (9)	0.0762 (10)	0.0393 (8)	0.0273 (8)	0.0373 (8)
O3	0.0646 (9)	0.0527 (8)	0.0686 (9)	0.0205 (7)	0.0149 (7)	0.0356 (7)
O4	0.0538 (7)	0.0499 (7)	0.0648 (8)	0.0269 (6)	0.0156 (6)	0.0239 (6)
N1	0.0313 (7)	0.0565 (9)	0.0502 (8)	0.0091 (6)	0.0079 (6)	0.0148 (7)
N2	0.0291 (6)	0.0539 (8)	0.0484 (8)	0.0135 (6)	0.0088 (5)	0.0125 (7)
N3	0.0279 (6)	0.0444 (7)	0.0417 (7)	0.0138 (5)	0.0086 (5)	0.0188 (6)
N4	0.0519 (9)	0.0524 (9)	0.0575 (9)	0.0239 (7)	0.0160 (7)	0.0192 (7)
N5	0.0414 (7)	0.0383 (7)	0.0397 (7)	0.0121 (6)	0.0057 (5)	0.0105 (6)
C1	0.0592 (11)	0.0546 (11)	0.0531 (11)	0.0214 (9)	0.0073 (9)	0.0173 (9)
C2	0.0670 (13)	0.0644 (13)	0.0534 (12)	0.0163 (11)	0.0188 (10)	0.0119 (10)
C3	0.0891 (16)	0.0424 (10)	0.0387 (9)	0.0044 (10)	0.0046 (9)	0.0104 (8)
C4	0.0881 (16)	0.0538 (11)	0.0527 (11)	0.0292 (11)	0.0012 (11)	0.0184 (9)
C5	0.0625 (12)	0.0569 (11)	0.0535 (11)	0.0246 (10)	0.0068 (9)	0.0158 (9)
C6	0.0491 (9)	0.0370 (8)	0.0423 (9)	0.0083 (7)	0.0009 (7)	0.0094 (7)
C7	0.0521 (10)	0.0431 (9)	0.0537 (10)	0.0030 (8)	0.0048 (8)	0.0174 (8)
C8	0.0383 (8)	0.0416 (8)	0.0431 (8)	0.0066 (6)	0.0086 (6)	0.0204 (7)
C9	0.0416 (8)	0.0415 (8)	0.0406 (8)	0.0156 (7)	0.0108 (6)	0.0219 (7)
C10	0.0301 (7)	0.0432 (8)	0.0385 (8)	0.0127 (6)	0.0112 (5)	0.0178 (6)
C11	0.0232 (6)	0.0506 (9)	0.0503 (9)	0.0161 (6)	0.0015 (6)	0.0079 (7)
C12	0.0439 (9)	0.0445 (9)	0.0519 (10)	0.0170 (7)	0.0130 (7)	0.0155 (8)
C13	0.0411 (8)	0.0362 (8)	0.0438 (9)	0.0137 (6)	0.0056 (6)	0.0107 (7)
C14	0.0381 (8)	0.0344 (7)	0.0391 (8)	0.0107 (6)	0.0050 (6)	0.0115 (6)
C15	0.0439 (9)	0.0358 (8)	0.0501 (9)	0.0131 (7)	0.0062 (7)	0.0136 (7)
C16	0.0524 (10)	0.0429 (9)	0.0364 (8)	0.0105 (7)	0.0069 (7)	0.0117 (7)
C17	0.0613 (12)	0.0568 (11)	0.0534 (11)	0.0045 (9)	−0.0046 (9)	0.0204 (9)
C18	0.0925 (18)	0.0740 (15)	0.0542 (12)	0.0134 (14)	−0.0123 (12)	0.0280 (11)
C19	0.105 (2)	0.0678 (15)	0.0543 (13)	0.0086 (14)	0.0090 (12)	0.0322 (11)
C20	0.0845 (17)	0.0686 (15)	0.0654 (14)	−0.0010 (13)	0.0162 (12)	0.0313 (12)
C21	0.0565 (11)	0.0627 (12)	0.0536 (11)	0.0033 (9)	0.0070 (9)	0.0217 (10)

Geometric parameters (Å, º) top

Cl1—C3	1.744 (2)	C5—H5A	0.9300
S1—C10	1.7472 (18)	C6—C7	1.513 (3)
S1—C12	1.7960 (17)	C7—C8	1.503 (3)
O1—C9	1.2159 (19)	C7—H7A	0.9700
O2—C13	1.209 (2)	C7—H7B	0.9700
O3—C15	1.197 (2)	C8—C9	1.468 (2)
O4—N4	1.370 (2)	C11—H11A	0.9600
O4—C15	1.420 (2)	C11—H11B	0.9600
N1—C8	1.295 (2)	C11—H11C	0.9600
N1—N2	1.381 (2)	C12—C13	1.513 (2)
N2—C10	1.292 (2)	C12—H12A	0.9700
N3—C10	1.3655 (18)	C12—H12B	0.9700
N3—C9	1.386 (2)	C13—C14	1.463 (2)
N3—C11	1.4055 (19)	C14—C15	1.422 (2)
N4—N5	1.3046 (19)	C16—C17	1.377 (3)
N5—C14	1.358 (2)	C16—C21	1.383 (3)
N5—C16	1.449 (2)	C17—C18	1.383 (3)
C1—C6	1.381 (3)	C17—H17A	0.9300
C1—C2	1.388 (3)	C18—C19	1.379 (4)
C1—H1A	0.9300	C18—H18A	0.9300
C2—C3	1.375 (3)	C19—C20	1.377 (4)
C2—H2A	0.9300	C19—H19A	0.9300
C3—C4	1.365 (3)	C20—C21	1.386 (3)
C4—C5	1.382 (3)	C20—H20A	0.9300
C4—H4A	0.9300	C21—H21A	0.9300
C5—C6	1.387 (3)

C10—S1—C12	100.06 (8)	N2—C10—S1	121.47 (12)
N4—O4—C15	110.86 (12)	N3—C10—S1	114.61 (11)
C8—N1—N2	120.99 (14)	N3—C11—H11A	109.5
C10—N2—N1	118.28 (14)	N3—C11—H11B	109.5
C10—N3—C9	121.17 (13)	H11A—C11—H11B	109.5
C10—N3—C11	117.25 (14)	N3—C11—H11C	109.5
C9—N3—C11	121.14 (13)	H11A—C11—H11C	109.5
N5—N4—O4	105.20 (13)	H11B—C11—H11C	109.5
N4—N5—C14	114.60 (14)	C13—C12—S1	113.61 (12)
N4—N5—C16	114.42 (14)	C13—C12—H12A	108.8
C14—N5—C16	130.97 (13)	S1—C12—H12A	108.8
C6—C1—C2	120.63 (18)	C13—C12—H12B	108.8
C6—C1—H1A	119.7	S1—C12—H12B	108.8
C2—C1—H1A	119.7	H12A—C12—H12B	107.7
C3—C2—C1	119.2 (2)	O2—C13—C14	122.62 (16)
C3—C2—H2A	120.4	O2—C13—C12	123.39 (15)
C1—C2—H2A	120.4	C14—C13—C12	113.98 (14)
C4—C3—C2	121.4 (2)	N5—C14—C15	105.91 (13)
C4—C3—Cl1	119.07 (17)	N5—C14—C13	126.38 (14)
C2—C3—Cl1	119.57 (19)	C15—C14—C13	127.49 (15)
C3—C4—C5	119.04 (19)	O3—C15—O4	120.05 (15)
C3—C4—H4A	120.5	O3—C15—C14	136.52 (17)
C5—C4—H4A	120.5	O4—C15—C14	103.43 (14)
C4—C5—C6	121.2 (2)	C17—C16—C21	122.79 (18)
C4—C5—H5A	119.4	C17—C16—N5	119.23 (17)
C6—C5—H5A	119.4	C21—C16—N5	117.87 (16)
C1—C6—C5	118.58 (18)	C16—C17—C18	117.6 (2)
C1—C6—C7	121.61 (17)	C16—C17—H17A	121.2
C5—C6—C7	119.59 (17)	C18—C17—H17A	121.2
C8—C7—C6	108.29 (14)	C19—C18—C17	120.9 (2)
C8—C7—H7A	110.0	C19—C18—H18A	119.5
C6—C7—H7A	110.0	C17—C18—H18A	119.5
C8—C7—H7B	110.0	C20—C19—C18	120.3 (2)
C6—C7—H7B	110.0	C20—C19—H19A	119.8
H7A—C7—H7B	108.4	C18—C19—H19A	119.8
N1—C8—C9	123.14 (16)	C19—C20—C21	120.1 (2)
N1—C8—C7	118.42 (16)	C19—C20—H20A	120.0
C9—C8—C7	118.25 (15)	C21—C20—H20A	120.0
O1—C9—N3	122.23 (16)	C16—C21—C20	118.2 (2)
O1—C9—C8	125.41 (17)	C16—C21—H21A	120.9
N3—C9—C8	112.36 (13)	C20—C21—H21A	120.9
N2—C10—N3	123.91 (16)

C8—N1—N2—C10	0.0 (2)	C11—N3—C10—S1	−1.28 (19)
C15—O4—N4—N5	−0.1 (2)	C12—S1—C10—N2	4.33 (16)
O4—N4—N5—C14	0.5 (2)	C12—S1—C10—N3	−176.91 (12)
O4—N4—N5—C16	179.66 (14)	C10—S1—C12—C13	87.66 (14)
C6—C1—C2—C3	0.0 (3)	S1—C12—C13—O2	−7.7 (2)
C1—C2—C3—C4	−1.3 (3)	S1—C12—C13—C14	171.37 (13)
C1—C2—C3—Cl1	177.98 (17)	N4—N5—C14—C15	−0.7 (2)
C2—C3—C4—C5	1.7 (3)	C16—N5—C14—C15	−179.67 (17)
Cl1—C3—C4—C5	−177.58 (17)	N4—N5—C14—C13	−175.56 (16)
C3—C4—C5—C6	−0.8 (3)	C16—N5—C14—C13	5.5 (3)
C2—C1—C6—C5	0.8 (3)	O2—C13—C14—N5	−0.6 (3)
C2—C1—C6—C7	−173.70 (19)	C12—C13—C14—N5	−179.66 (16)
C4—C5—C6—C1	−0.4 (3)	O2—C13—C14—C15	−174.35 (19)
C4—C5—C6—C7	174.22 (19)	C12—C13—C14—C15	6.6 (3)
C1—C6—C7—C8	94.1 (2)	N4—O4—C15—O3	179.13 (17)
C5—C6—C7—C8	−80.3 (2)	N4—O4—C15—C14	−0.28 (19)
N2—N1—C8—C9	0.8 (3)	N5—C14—C15—O3	−178.7 (2)
N2—N1—C8—C7	−174.08 (15)	C13—C14—C15—O3	−3.9 (4)
C6—C7—C8—N1	91.90 (19)	N5—C14—C15—O4	0.54 (18)
C6—C7—C8—C9	−83.27 (19)	C13—C14—C15—O4	175.34 (16)
C10—N3—C9—O1	176.61 (15)	N4—N5—C16—C17	−122.28 (19)
C11—N3—C9—O1	4.5 (2)	C14—N5—C16—C17	56.7 (3)
C10—N3—C9—C8	−3.8 (2)	N4—N5—C16—C21	54.0 (2)
C11—N3—C9—C8	−175.91 (14)	C14—N5—C16—C21	−127.0 (2)
N1—C8—C9—O1	−179.33 (17)	C21—C16—C17—C18	−1.0 (3)
C7—C8—C9—O1	−4.4 (2)	N5—C16—C17—C18	175.10 (19)
N1—C8—C9—N3	1.0 (2)	C16—C17—C18—C19	−0.3 (4)
C7—C8—C9—N3	175.98 (14)	C17—C18—C19—C20	1.7 (4)
N1—N2—C10—N3	−2.9 (2)	C18—C19—C20—C21	−1.8 (4)
N1—N2—C10—S1	175.76 (12)	C17—C16—C21—C20	0.8 (3)
C9—N3—C10—N2	5.0 (2)	N5—C16—C21—C20	−175.31 (19)
C11—N3—C10—N2	177.45 (16)	C19—C20—C21—C16	0.6 (4)
C9—N3—C10—S1	−173.73 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O2ⁱ	0.97	2.52	3.429 (3)	157
C11—H11A···S1	0.96	2.12	2.7577 (17)	122
C11—H11B···N1ⁱⁱ	0.96	2.36	3.066 (2)	130
C11—H11B···N2ⁱⁱ	0.96	2.40	3.0304 (19)	123
C11—H11C···O1ⁱⁱⁱ	0.96	2.07	3.021 (2)	169

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆ClN₅O₄S
M_r	469.90
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.4604 (1), 10.1634 (2), 16.9901 (4)
α, β, γ (°)	105.264 (1), 92.103 (1), 97.363 (1)
V (Å³)	1064.44 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.62 × 0.39 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.828, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	21841, 6389, 4781
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.713

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.154, 1.05
No. of reflections	6389
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.49

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
C7—H7B···O2ⁱ	0.97	2.52	3.429 (3)	157
C11—H11A···S1	0.96	2.12	2.7577 (17)	122
C11—H11B···N1ⁱⁱ	0.96	2.36	3.066 (2)	130
C11—H11B···N2ⁱⁱ	0.96	2.40	3.0304 (19)	123
C11—H11C···O1ⁱⁱⁱ	0.96	2.07	3.021 (2)	169

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. 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
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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o820

doi:10.1107/S1600536811007689

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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