4-[2-(2-Benzyl­idene­hydrazin­ylidene)-3,6-dihydro-2H-1,3,4-thia­diazin-5-yl]-3-(4-meth­oxy­phen­yl)­sydnone

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

doi:10.1107/S1600536811009329

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o902

doi:10.1107/S1600536811009329

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4-[2-(2-Benzylidenehydrazinylidene)-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl]-3-(4-methoxyphenyl)sydnone

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 2 March 2011; accepted 11 March 2011; online 19 March 2011)

In the title compound, C₁₉H₁₆N₆O₃S, the 3,6-dihydro-1,3,4-thiadiazine ring adopts a twist-boat conformation. The dihedral angle between the methoxy-substituted benzene ring and the oxadiazole ring is 71.91 (7)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers via pairs of intermolecular N—H⋯N hydrogen bonds, generating R₂²(8) ring motifs. There is an intramolecular C—H⋯O hydrogen bond which generates an S(6) ring motif.

Related literature

For applications of sydnones, see: Baker et al. (1949 ); Hedge et al. (2008 ); Rai et al. (2008 ); Kalluraya et al. (2003 ). For the definition of ring-puckering parameters, see: Cremer & Pople (1975 ). For the definition of graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₆N₆O₃S
M_r = 408.44
Monoclinic, P 2₁ /n
a = 14.9236 (15) Å
b = 5.9331 (7) Å
c = 21.425 (2) Å
β = 99.338 (2)°
V = 1871.9 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.77 × 0.07 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.856, T_max = 0.992
15668 measured reflections
4269 independent reflections
2889 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.106
S = 1.03
4269 reflections
267 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N2ⁱ	0.87 (3)	2.04 (3)	2.905 (2)	173 (2)
C9—H9B⋯O2	0.97	2.39	3.057 (3)	126
Symmetry code: (i) -x+1, -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/S1600536811009329/rz2567sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811009329/rz2567Isup2.hkl

checkCIF report

Comment top

Sydnones constitute a well defined class of mesoionic compounds consisting of 1,2,3-oxadiazole ring system. The introduction of the concept of mesoionic structure for certain heterocyclic compounds in the year 1949 has proved to be a fruitful development in heterocyclic chemistry (Baker et al., 1949). The study of sydnones still remains a field of interest because of their electronic structures and also because of the various types of biological activities displayed by some of them. Interest in sydnone derivatives has also been encouraged by the discovery that they exhibit various pharmacological activities (Hedge et al., 2008; Rai et al., 2008). Encouraged by these reports and in continuation of our research for biologically active nitrogen-containing heterocycles, a thiadiazine moiety at the 4-position of the phenylsydnone was introduced. A series of thiadiazines were synthesized by the condensation of 4-bromoacetyl-3-arylsydnones with N'-[phenylmethylidene]carbonohydrazide. 4-Bromoacetyl-3-arylsydnones were in turn obtained by the photochemical bromination of 4-acetyl-3-arylsydnones (Kalluraya et al., 2003).

In the title compound (Fig. 1), the 3,6-dihydro-1,3,4-thiadiazine ring (C8–C10/N3/N4/S1) adopts twist-boat conformation, with puckering parameters Q = 0.5852 (18) Å, Θ = 109.67 (18)° and ϕ = 138.84 (19)° (Cremer & Pople, 1975). The dihedral angle between the methoxy-substituted benzene ring (C13–C18) and the oxadiazole ring (C11–C12/O1/N5–N6) is 71.91 (7)°. In the crystal structure (Fig. 2), centrosymmetrically related molecules are linked into dimers via pairs of intermolecular N—H···N hydrogen bonds, generating an R²₂(8) ring motif. There is an intramolecular C—H···O hydrogen bond which generates an S(6) ring motif.

Related literature top

For applications of sydnones, see: Baker et al. (1949); Hedge et al. (2008); Rai et al. (2008); Kalluraya et al. (2003). For the definition of ring-puckering parameters, see: Cremer & Pople (1975). For the definition of graph-set notation, see: Bernstein et al. (1995). [Please note added references and correct as necessary]

Experimental top

To a mixture of 4-bromoacetyl-3-(p-anisyl)sydnone (0.01 mol) and N'-(phenylmethylidene) carbonohydrazide (0.01 mol) 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 by slow evaporation of a DMF/ethanol solution (1:2 v/v).

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 viewed along the a axis. Intermolecular hydrogen bonds are shown as dashed lines.

4-[2-(2-Benzylidenehydrazinylidene)-3,6-dihydro-2H-1,3,4-thiadiazin- 5-yl]-3-(4-methoxyphenyl)-1,2,3-oxadiazol-3-ylium-5-olate top

Crystal data top

C₁₉H₁₆N₆O₃S	F(000) = 848
M_r = 408.44	D_x = 1.449 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1908 reflections
a = 14.9236 (15) Å	θ = 3.0–27.3°
b = 5.9331 (7) Å	µ = 0.21 mm⁻¹
c = 21.425 (2) Å	T = 296 K
β = 99.338 (2)°	Needle, orange
V = 1871.9 (4) Å³	0.77 × 0.07 × 0.04 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4269 independent reflections
Radiation source: fine-focus sealed tube	2889 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.062
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
T_min = 0.856, T_max = 0.992	k = −7→7
15668 measured reflections	l = −27→27

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0401P)² + 0.4767P] where P = (F_o² + 2F_c²)/3
4269 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₉H₁₆N₆O₃S	V = 1871.9 (4) Å³
M_r = 408.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.9236 (15) Å	µ = 0.21 mm⁻¹
b = 5.9331 (7) Å	T = 296 K
c = 21.425 (2) Å	0.77 × 0.07 × 0.04 mm
β = 99.338 (2)°

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	4269 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2889 reflections with I > 2σ(I)
T_min = 0.856, T_max = 0.992	R_int = 0.062
15668 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
4269 reflections	Δρ_min = −0.29 e Å⁻³
267 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
S1	0.51196 (3)	0.06066 (11)	0.18109 (2)	0.02408 (16)
O1	0.29051 (9)	−0.7158 (3)	0.24009 (6)	0.0274 (4)
O2	0.43051 (9)	−0.5875 (3)	0.28329 (6)	0.0261 (4)
O3	0.03886 (9)	−0.2449 (3)	−0.06332 (6)	0.0302 (4)
N1	0.58722 (11)	0.3462 (3)	0.10107 (7)	0.0197 (4)
N2	0.53281 (10)	0.1897 (3)	0.06401 (7)	0.0203 (4)
N3	0.45763 (11)	−0.1430 (3)	0.06974 (7)	0.0189 (4)
N4	0.39709 (10)	−0.2843 (3)	0.09276 (7)	0.0185 (4)
N5	0.26615 (11)	−0.5345 (3)	0.15329 (7)	0.0202 (4)
N6	0.22703 (11)	−0.6811 (4)	0.18620 (7)	0.0264 (5)
C1	0.73234 (13)	0.6171 (4)	0.16329 (9)	0.0242 (5)
H1A	0.7205	0.4846	0.1837	0.029*
C2	0.79578 (14)	0.7681 (5)	0.19293 (10)	0.0320 (6)
H2A	0.8264	0.7369	0.2334	0.038*
C3	0.81414 (15)	0.9647 (5)	0.16313 (11)	0.0339 (6)
H3A	0.8574	1.0645	0.1833	0.041*
C4	0.76819 (14)	1.0137 (5)	0.10314 (10)	0.0287 (6)
H4A	0.7796	1.1476	0.0833	0.034*
C5	0.70513 (13)	0.8620 (4)	0.07295 (9)	0.0230 (5)
H5A	0.6753	0.8936	0.0323	0.028*
C6	0.68565 (13)	0.6638 (4)	0.10230 (8)	0.0199 (5)
C7	0.62003 (13)	0.5032 (4)	0.06982 (8)	0.0204 (5)
H7A	0.6018	0.5142	0.0263	0.025*
C8	0.50177 (12)	0.0383 (4)	0.09904 (8)	0.0181 (5)
C9	0.49414 (13)	−0.2359 (4)	0.19578 (8)	0.0221 (5)
H9A	0.5470	−0.3213	0.1886	0.026*
H9B	0.4866	−0.2566	0.2395	0.026*
C10	0.41158 (12)	−0.3220 (4)	0.15311 (8)	0.0191 (5)
C11	0.34998 (13)	−0.4661 (4)	0.18046 (8)	0.0189 (5)
C12	0.36813 (13)	−0.5822 (4)	0.23935 (8)	0.0220 (5)
C13	0.21053 (12)	−0.4579 (4)	0.09497 (8)	0.0199 (5)
C14	0.17263 (14)	−0.2452 (4)	0.09297 (9)	0.0240 (5)
H14A	0.1857	−0.1480	0.1273	0.029*
C15	0.11479 (14)	−0.1796 (5)	0.03878 (9)	0.0266 (5)
H15A	0.0881	−0.0376	0.0365	0.032*
C16	0.09668 (13)	−0.3280 (5)	−0.01245 (8)	0.0227 (5)
C17	0.13592 (13)	−0.5395 (5)	−0.00988 (9)	0.0247 (5)
H17A	0.1242	−0.6363	−0.0444	0.030*
C18	0.19321 (13)	−0.6064 (4)	0.04498 (9)	0.0234 (5)
H18A	0.2194	−0.7490	0.0478	0.028*
C19	0.01814 (14)	−0.3879 (5)	−0.11771 (9)	0.0340 (7)
H19A	−0.0240	−0.3128	−0.1496	0.051*
H19B	−0.0084	−0.5258	−0.1059	0.051*
H19C	0.0729	−0.4210	−0.1340	0.051*
H1N3	0.4553 (16)	−0.161 (5)	0.0291 (12)	0.041 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0287 (3)	0.0285 (4)	0.0149 (2)	−0.0068 (3)	0.00304 (18)	−0.0044 (2)
O1	0.0302 (8)	0.0318 (12)	0.0200 (6)	−0.0042 (8)	0.0033 (6)	0.0077 (7)
O2	0.0281 (7)	0.0319 (12)	0.0177 (6)	0.0013 (8)	0.0016 (5)	0.0023 (7)
O3	0.0242 (7)	0.0414 (13)	0.0238 (7)	0.0037 (8)	0.0003 (6)	0.0051 (7)
N1	0.0198 (8)	0.0190 (12)	0.0199 (7)	−0.0040 (9)	0.0022 (6)	−0.0060 (8)
N2	0.0207 (8)	0.0229 (13)	0.0170 (7)	−0.0048 (9)	0.0018 (6)	−0.0034 (8)
N3	0.0239 (8)	0.0198 (12)	0.0134 (7)	−0.0055 (9)	0.0043 (6)	−0.0014 (7)
N4	0.0185 (8)	0.0200 (12)	0.0176 (7)	−0.0032 (8)	0.0046 (6)	−0.0006 (7)
N5	0.0213 (8)	0.0217 (12)	0.0186 (7)	−0.0008 (9)	0.0059 (6)	0.0017 (8)
N6	0.0282 (9)	0.0287 (14)	0.0218 (8)	−0.0087 (10)	0.0021 (7)	0.0045 (8)
C1	0.0245 (10)	0.0246 (16)	0.0233 (9)	0.0005 (11)	0.0030 (8)	0.0008 (10)
C2	0.0273 (11)	0.0363 (19)	0.0287 (10)	−0.0002 (13)	−0.0061 (9)	−0.0048 (11)
C3	0.0263 (11)	0.0294 (18)	0.0441 (12)	−0.0085 (12)	0.0003 (10)	−0.0118 (12)
C4	0.0258 (10)	0.0220 (16)	0.0404 (11)	−0.0015 (11)	0.0113 (9)	−0.0006 (11)
C5	0.0225 (10)	0.0235 (15)	0.0237 (9)	0.0006 (11)	0.0063 (8)	0.0005 (10)
C6	0.0188 (9)	0.0213 (15)	0.0203 (9)	−0.0011 (10)	0.0052 (7)	−0.0033 (9)
C7	0.0216 (9)	0.0217 (15)	0.0175 (8)	0.0005 (10)	0.0021 (7)	−0.0023 (9)
C8	0.0156 (8)	0.0227 (14)	0.0156 (8)	0.0003 (10)	0.0011 (7)	−0.0040 (9)
C9	0.0215 (9)	0.0277 (16)	0.0166 (8)	−0.0040 (11)	0.0018 (7)	0.0024 (9)
C10	0.0187 (9)	0.0217 (15)	0.0173 (8)	0.0001 (10)	0.0042 (7)	−0.0026 (9)
C11	0.0191 (9)	0.0207 (14)	0.0172 (8)	0.0008 (10)	0.0039 (7)	−0.0004 (9)
C12	0.0259 (10)	0.0223 (15)	0.0196 (9)	0.0026 (11)	0.0093 (8)	−0.0001 (9)
C13	0.0165 (9)	0.0244 (15)	0.0187 (8)	−0.0056 (10)	0.0026 (7)	−0.0009 (9)
C14	0.0274 (10)	0.0234 (15)	0.0219 (9)	−0.0004 (12)	0.0059 (8)	−0.0014 (10)
C15	0.0297 (11)	0.0238 (16)	0.0271 (10)	0.0012 (12)	0.0069 (8)	0.0014 (10)
C16	0.0161 (9)	0.0309 (17)	0.0215 (9)	−0.0018 (11)	0.0047 (7)	0.0035 (10)
C17	0.0235 (10)	0.0282 (16)	0.0226 (9)	−0.0046 (12)	0.0041 (8)	−0.0049 (10)
C18	0.0211 (9)	0.0241 (16)	0.0251 (9)	−0.0014 (11)	0.0039 (8)	−0.0023 (10)
C19	0.0268 (11)	0.051 (2)	0.0227 (10)	−0.0061 (13)	−0.0011 (8)	0.0030 (11)

Geometric parameters (Å, º) top

S1—C8	1.7448 (17)	C4—C5	1.384 (3)
S1—C9	1.814 (3)	C4—H4A	0.9300
O1—N6	1.385 (2)	C5—C6	1.387 (3)
O1—C12	1.406 (3)	C5—H5A	0.9300
O2—C12	1.212 (2)	C6—C7	1.459 (3)
O3—C16	1.368 (2)	C7—H7A	0.9300
O3—C19	1.434 (3)	C9—C10	1.500 (3)
N1—C7	1.289 (3)	C9—H9A	0.9700
N1—N2	1.394 (2)	C9—H9B	0.9700
N2—C8	1.303 (3)	C10—C11	1.447 (3)
N3—C8	1.360 (3)	C11—C12	1.425 (3)
N3—N4	1.381 (2)	C13—C18	1.379 (3)
N3—H1N3	0.87 (2)	C13—C14	1.381 (3)
N4—C10	1.295 (2)	C14—C15	1.385 (3)
N5—N6	1.314 (2)	C14—H14A	0.9300
N5—C11	1.354 (2)	C15—C16	1.399 (3)
N5—C13	1.456 (2)	C15—H15A	0.9300
C1—C2	1.381 (3)	C16—C17	1.382 (3)
C1—C6	1.405 (3)	C17—C18	1.394 (3)
C1—H1A	0.9300	C17—H17A	0.9300
C2—C3	1.378 (4)	C18—H18A	0.9300
C2—H2A	0.9300	C19—H19A	0.9600
C3—C4	1.386 (3)	C19—H19B	0.9600
C3—H3A	0.9300	C19—H19C	0.9600

C8—S1—C9	96.30 (10)	C10—C9—H9A	109.5
N6—O1—C12	111.11 (15)	S1—C9—H9A	109.5
C16—O3—C19	117.3 (2)	C10—C9—H9B	109.5
C7—N1—N2	114.88 (15)	S1—C9—H9B	109.5
C8—N2—N1	111.09 (15)	H9A—C9—H9B	108.1
C8—N3—N4	127.66 (15)	N4—C10—C11	119.49 (18)
C8—N3—H1N3	119.9 (18)	N4—C10—C9	122.47 (18)
N4—N3—H1N3	111.0 (17)	C11—C10—C9	117.88 (16)
C10—N4—N3	116.66 (16)	N5—C11—C12	105.40 (18)
N6—N5—C11	115.31 (16)	N5—C11—C10	127.34 (17)
N6—N5—C13	115.21 (16)	C12—C11—C10	127.04 (17)
C11—N5—C13	129.33 (17)	O2—C12—O1	120.48 (19)
N5—N6—O1	104.03 (15)	O2—C12—C11	135.4 (2)
C2—C1—C6	119.9 (2)	O1—C12—C11	104.12 (16)
C2—C1—H1A	120.0	C18—C13—C14	122.39 (19)
C6—C1—H1A	120.0	C18—C13—N5	118.4 (2)
C3—C2—C1	120.6 (2)	C14—C13—N5	119.06 (18)
C3—C2—H2A	119.7	C13—C14—C15	118.6 (2)
C1—C2—H2A	119.7	C13—C14—H14A	120.7
C2—C3—C4	120.1 (2)	C15—C14—H14A	120.7
C2—C3—H3A	120.0	C14—C15—C16	119.7 (2)
C4—C3—H3A	120.0	C14—C15—H15A	120.1
C5—C4—C3	119.6 (2)	C16—C15—H15A	120.1
C5—C4—H4A	120.2	O3—C16—C17	124.6 (2)
C3—C4—H4A	120.2	O3—C16—C15	114.5 (2)
C4—C5—C6	121.07 (19)	C17—C16—C15	120.89 (19)
C4—C5—H5A	119.5	C16—C17—C18	119.3 (2)
C6—C5—H5A	119.5	C16—C17—H17A	120.3
C5—C6—C1	118.7 (2)	C18—C17—H17A	120.3
C5—C6—C7	120.74 (18)	C13—C18—C17	119.0 (2)
C1—C6—C7	120.5 (2)	C13—C18—H18A	120.5
N1—C7—C6	120.39 (17)	C17—C18—H18A	120.5
N1—C7—H7A	119.8	O3—C19—H19A	109.5
C6—C7—H7A	119.8	O3—C19—H19B	109.5
N2—C8—N3	118.03 (16)	H19A—C19—H19B	109.5
N2—C8—S1	123.16 (17)	O3—C19—H19C	109.5
N3—C8—S1	118.79 (15)	H19A—C19—H19C	109.5
C10—C9—S1	110.72 (15)	H19B—C19—H19C	109.5

C7—N1—N2—C8	−179.44 (19)	N6—N5—C11—C10	174.4 (2)
C8—N3—N4—C10	−33.8 (3)	C13—N5—C11—C10	−10.3 (4)
C11—N5—N6—O1	−0.5 (2)	N4—C10—C11—N5	−14.9 (4)
C13—N5—N6—O1	−176.51 (17)	C9—C10—C11—N5	169.6 (2)
C12—O1—N6—N5	1.3 (2)	N4—C10—C11—C12	158.9 (2)
C6—C1—C2—C3	−0.2 (3)	C9—C10—C11—C12	−16.6 (3)
C1—C2—C3—C4	0.7 (4)	N6—O1—C12—O2	178.8 (2)
C2—C3—C4—C5	−1.3 (3)	N6—O1—C12—C11	−1.6 (2)
C3—C4—C5—C6	1.4 (3)	N5—C11—C12—O2	−179.3 (3)
C4—C5—C6—C1	−1.0 (3)	C10—C11—C12—O2	5.8 (4)
C4—C5—C6—C7	−179.12 (19)	N5—C11—C12—O1	1.2 (2)
C2—C1—C6—C5	0.4 (3)	C10—C11—C12—O1	−173.7 (2)
C2—C1—C6—C7	178.52 (19)	N6—N5—C13—C18	−71.5 (2)
N2—N1—C7—C6	−173.51 (17)	C11—N5—C13—C18	113.2 (3)
C5—C6—C7—N1	−164.7 (2)	N6—N5—C13—C14	104.6 (2)
C1—C6—C7—N1	17.2 (3)	C11—N5—C13—C14	−70.7 (3)
N1—N2—C8—N3	−171.36 (17)	C18—C13—C14—C15	0.3 (3)
N1—N2—C8—S1	10.1 (2)	N5—C13—C14—C15	−175.62 (17)
N4—N3—C8—N2	−158.81 (19)	C13—C14—C15—C16	−0.5 (3)
N4—N3—C8—S1	19.8 (3)	C19—O3—C16—C17	−0.3 (3)
C9—S1—C8—N2	−160.46 (18)	C19—O3—C16—C15	179.43 (17)
C9—S1—C8—N3	21.05 (18)	C14—C15—C16—O3	−179.88 (18)
C8—S1—C9—C10	−49.20 (14)	C14—C15—C16—C17	−0.1 (3)
N3—N4—C10—C11	179.15 (19)	O3—C16—C17—C18	−179.35 (17)
N3—N4—C10—C9	−5.5 (3)	C15—C16—C17—C18	1.0 (3)
S1—C9—C10—N4	48.2 (3)	C14—C13—C18—C17	0.5 (3)
S1—C9—C10—C11	−136.34 (18)	N5—C13—C18—C17	176.44 (17)
N6—N5—C11—C12	−0.4 (3)	C16—C17—C18—C13	−1.1 (3)
C13—N5—C11—C12	174.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N2ⁱ	0.87 (3)	2.04 (3)	2.905 (2)	173 (2)
C9—H9B···O2	0.97	2.39	3.057 (3)	126

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆N₆O₃S
M_r	408.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	14.9236 (15), 5.9331 (7), 21.425 (2)
β (°)	99.338 (2)
V (Å³)	1871.9 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.77 × 0.07 × 0.04

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.856, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	15668, 4269, 2889
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.106, 1.03
No. of reflections	4269
No. of parameters	267
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.29

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
N3—H1N3···N2ⁱ	0.87 (3)	2.04 (3)	2.905 (2)	173 (2)
C9—H9B···O2	0.9700	2.3900	3.057 (3)	126.00

Symmetry code: (i) −x+1, −y, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

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

References

Baker, W., Ollis, W. D. & Poole, V. D. (1949). J. Chem. Soc. pp. 307–314. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Hedge, J. C., Girisha, K. S., Adhikari, A. & Kalluraya, B. (2008). Eur. J. Med. Chem. 43, 2831–2834. Web of Science PubMed Google Scholar
Kalluraya, B., Vishwanatha, P., Hedge, J. C., Priya, V. F. & Rai, G. (2003). Indian J. Heterocycl. Chem. 12, 355–356. 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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4-[2-(2-Benzyl­­idene­hydrazin­yl­idene)-3,6-di­hydro-2H-1,3,4-thia­diazin-5-yl]-3-(4-meth­­oxy­phen­yl)­sydnone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-[2-(2-Benzylidenehydrazinylidene)-3,6-dihydro-2H-1,3,4-thiadiazin-5-yl]-3-(4-methoxyphenyl)sydnone