4-{(Z)-2-[(E)-Benzyl-idenehydrazinyl-idene]-3,6-dihydro-2H-1,3,4-thia-diazin-5-yl}-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate.

The title compound, C(18)H(14)N(6)O(2)S, exists in trans and cis configurations with respect to the two acyclic C=N bonds [bond lengths = 1.2835 (9) and 1.3049 (9) Å]. The 3,6-dihydro-2H-1,3,4-thia-diazine ring adopts a half-boat conformation. The oxadiazol-3-ium ring makes dihedral angles of 53.70 (4) and 60.26 (4)° with the two phenyl rings. In the crystal, mol-ecules are linked via pairs of inter-molecular N-H⋯N hydrogen bonds, generating R(2) (2)(8) ring motifs, and are further linked via inter-molecular C-H⋯O and C-H⋯S hydrogen bonds into a three-dimensional network. The short inter-molecular distance between the oxadiazol-3-ium rings [3.4154 (4) Å] indicates the existence of a π-π inter-action.

Related literature

For general background to and the biological activity of sydnone derivatives, see: Newton & Ramsden (1982 ▶); Wagner & Hill (1974 ▶); Kalluraya & Rahiman (1997 ▶). For the preparation, see: Kalluraya et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C18H14N6O2S

M = 378.41

Triclinic,

a = 6.8752 (2) Å

b = 10.1335 (3) Å

c = 12.7374 (4) Å

α = 78.578 (1)°

β = 88.984 (1)°

γ = 85.874 (1)°

V = 867.58 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.58 × 0.27 × 0.08 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.885, T max = 0.982

29236 measured reflections

7567 independent reflections

6818 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.101

S = 1.03

7567 reflections

248 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.37 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/S1600536811010609/sj5123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010609/sj5123Isup2.hkl

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

C18H14N6O2S	Z = 2
Mr = 378.41	F(000) = 392
Triclinic, P1	Dx = 1.449 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8752 (2) Å	Cell parameters from 9935 reflections
b = 10.1335 (3) Å	θ = 2.9–37.5°
c = 12.7374 (4) Å	µ = 0.21 mm−1
α = 78.578 (1)°	T = 100 K
β = 88.984 (1)°	Block, yellow
γ = 85.874 (1)°	0.58 × 0.27 × 0.08 mm
V = 867.58 (5) Å3

Bruker SMART APEXII DUO CCD area-detector diffractometer	7567 independent reflections
Radiation source: fine-focus sealed tube	6818 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 35.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.885, Tmax = 0.982	k = −16→16
29236 measured reflections	l = −20→20

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0601P)2 + 0.2223P] where P = (Fo2 + 2Fc2)/3
7567 reflections	(Δ/σ)max = 0.001
248 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.30498 (3)	0.783931 (19)	0.313847 (14)	0.01687 (5)
O1	0.78647 (9)	1.04039 (5)	−0.06087 (4)	0.01590 (10)
O2	0.64969 (9)	1.17463 (5)	0.04865 (5)	0.01895 (11)
N1	0.14753 (10)	0.81808 (6)	0.50454 (5)	0.01503 (11)
N2	0.31270 (10)	0.89086 (6)	0.48880 (5)	0.01459 (11)
N3	0.57604 (10)	0.93168 (6)	0.37674 (5)	0.01437 (10)
N4	0.65689 (9)	0.96382 (6)	0.27631 (5)	0.01327 (10)
N5	0.83490 (10)	0.90536 (6)	−0.05820 (5)	0.01491 (11)
N6	0.78483 (9)	0.84631 (6)	0.03858 (5)	0.01194 (10)
C1	−0.17886 (12)	0.66190 (8)	0.55457 (6)	0.01753 (12)
H1A	−0.0967	0.6423	0.5001	0.021*
C2	−0.34245 (13)	0.58975 (8)	0.58220 (7)	0.02162 (14)
H2A	−0.3682	0.5208	0.5470	0.026*
C3	−0.46864 (12)	0.62002 (9)	0.66263 (7)	0.02278 (15)
H3A	−0.5789	0.5721	0.6802	0.027*
C4	−0.42941 (12)	0.72184 (8)	0.71643 (7)	0.02058 (14)
H4A	−0.5135	0.7423	0.7698	0.025*
C5	−0.26331 (11)	0.79319 (7)	0.68997 (6)	0.01674 (12)
H5A	−0.2362	0.8604	0.7267	0.020*
C6	−0.13718 (11)	0.76450 (7)	0.60870 (5)	0.01428 (11)
C7	0.03747 (11)	0.83958 (7)	0.58273 (6)	0.01507 (12)
H7A	0.0684	0.9026	0.6227	0.018*
C8	0.40347 (10)	0.87300 (7)	0.40132 (5)	0.01289 (11)
C9	0.52692 (13)	0.75797 (7)	0.23945 (6)	0.01832 (13)
H9A	0.6125	0.6886	0.2826	0.022*
H9B	0.4953	0.7268	0.1749	0.022*
C10	0.63071 (10)	0.88567 (7)	0.20958 (5)	0.01271 (11)
C11	0.70776 (10)	0.92958 (6)	0.10204 (5)	0.01202 (10)
C12	0.70589 (10)	1.06188 (7)	0.03802 (5)	0.01354 (11)
C13	0.82190 (10)	0.70199 (7)	0.06881 (5)	0.01254 (11)
C14	0.73006 (11)	0.61939 (7)	0.01353 (6)	0.01455 (11)
H14A	0.6507	0.6558	−0.0449	0.017*
C15	0.76016 (11)	0.48012 (7)	0.04823 (7)	0.01743 (13)
H15A	0.7000	0.4223	0.0128	0.021*
C16	0.87966 (12)	0.42727 (7)	0.13554 (7)	0.01914 (13)
H16A	0.8974	0.3343	0.1588	0.023*
C17	0.97311 (13)	0.51258 (8)	0.18857 (7)	0.01997 (14)
H17A	1.0547	0.4764	0.2461	0.024*
C18	0.94424 (11)	0.65205 (7)	0.15537 (6)	0.01683 (12)
H18A	1.0052	0.7101	0.1902	0.020*
H1N3	0.607 (2)	0.9855 (15)	0.4163 (12)	0.029 (3)*

	U11	U22	U33	U12	U13	U23
S1	0.01861 (9)	0.02017 (9)	0.01455 (8)	−0.00900 (6)	0.00407 (6)	−0.00768 (6)
O1	0.0196 (2)	0.0137 (2)	0.0136 (2)	−0.00159 (18)	0.00192 (18)	−0.00089 (16)
O2	0.0219 (3)	0.0114 (2)	0.0231 (3)	0.00014 (18)	0.0021 (2)	−0.00294 (18)
N1	0.0161 (3)	0.0161 (2)	0.0132 (2)	−0.0050 (2)	0.00206 (19)	−0.00282 (18)
N2	0.0162 (3)	0.0164 (2)	0.0120 (2)	−0.0053 (2)	0.00244 (19)	−0.00370 (18)
N3	0.0157 (3)	0.0175 (2)	0.0113 (2)	−0.0056 (2)	0.00213 (19)	−0.00495 (18)
N4	0.0143 (2)	0.0144 (2)	0.0118 (2)	−0.00285 (18)	0.00189 (18)	−0.00367 (17)
N5	0.0180 (3)	0.0141 (2)	0.0126 (2)	−0.00152 (19)	0.00223 (19)	−0.00250 (18)
N6	0.0129 (2)	0.0116 (2)	0.0117 (2)	−0.00116 (17)	0.00069 (18)	−0.00305 (17)
C1	0.0191 (3)	0.0174 (3)	0.0166 (3)	−0.0043 (2)	−0.0004 (2)	−0.0035 (2)
C2	0.0211 (3)	0.0196 (3)	0.0245 (3)	−0.0070 (3)	−0.0030 (3)	−0.0028 (3)
C3	0.0163 (3)	0.0216 (3)	0.0282 (4)	−0.0053 (3)	−0.0003 (3)	0.0020 (3)
C4	0.0157 (3)	0.0206 (3)	0.0228 (3)	−0.0006 (2)	0.0038 (3)	0.0016 (3)
C5	0.0169 (3)	0.0153 (3)	0.0170 (3)	−0.0006 (2)	0.0025 (2)	−0.0010 (2)
C6	0.0153 (3)	0.0135 (2)	0.0135 (2)	−0.0024 (2)	0.0004 (2)	−0.0008 (2)
C7	0.0171 (3)	0.0151 (3)	0.0134 (3)	−0.0038 (2)	0.0023 (2)	−0.0029 (2)
C8	0.0150 (3)	0.0125 (2)	0.0114 (2)	−0.0027 (2)	0.0007 (2)	−0.00234 (19)
C9	0.0240 (3)	0.0139 (3)	0.0188 (3)	−0.0064 (2)	0.0084 (3)	−0.0063 (2)
C10	0.0145 (3)	0.0114 (2)	0.0126 (2)	−0.0022 (2)	0.0021 (2)	−0.00294 (19)
C11	0.0133 (3)	0.0109 (2)	0.0122 (2)	−0.00156 (19)	0.0016 (2)	−0.00314 (18)
C12	0.0138 (3)	0.0126 (2)	0.0142 (3)	−0.0017 (2)	0.0007 (2)	−0.0023 (2)
C13	0.0131 (3)	0.0111 (2)	0.0136 (2)	−0.00038 (19)	0.0008 (2)	−0.00321 (19)
C14	0.0138 (3)	0.0141 (3)	0.0168 (3)	−0.0015 (2)	0.0006 (2)	−0.0055 (2)
C15	0.0155 (3)	0.0136 (3)	0.0242 (3)	−0.0027 (2)	0.0037 (2)	−0.0061 (2)
C16	0.0182 (3)	0.0134 (3)	0.0244 (3)	0.0003 (2)	0.0049 (3)	−0.0012 (2)
C17	0.0205 (3)	0.0171 (3)	0.0203 (3)	0.0034 (2)	−0.0016 (3)	−0.0006 (2)
C18	0.0173 (3)	0.0162 (3)	0.0170 (3)	0.0009 (2)	−0.0030 (2)	−0.0037 (2)

S1—C8	1.7400 (7)	C4—C5	1.3961 (11)
S1—C9	1.8126 (8)	C4—H4A	0.9300
O1—N5	1.3787 (8)	C5—C6	1.3996 (10)
O1—C12	1.4168 (9)	C5—H5A	0.9300
O2—C12	1.2120 (8)	C6—C7	1.4655 (10)
N1—C7	1.2835 (9)	C7—H7A	0.9300
N1—N2	1.3884 (9)	C9—C10	1.5022 (10)
N2—C8	1.3049 (9)	C9—H9A	0.9700
N3—C8	1.3689 (9)	C9—H9B	0.9700
N3—N4	1.3737 (8)	C10—C11	1.4567 (9)
N3—H1N3	0.852 (15)	C11—C12	1.4238 (9)
N4—C10	1.2940 (9)	C13—C14	1.3857 (10)
N5—N6	1.3110 (8)	C13—C18	1.3892 (10)
N6—C11	1.3553 (9)	C14—C15	1.3944 (10)
N6—C13	1.4418 (9)	C14—H14A	0.9300
C1—C2	1.3878 (11)	C15—C16	1.3898 (12)
C1—C6	1.4044 (10)	C15—H15A	0.9300
C1—H1A	0.9300	C16—C17	1.3940 (12)
C2—C3	1.3967 (13)	C16—H16A	0.9300
C2—H2A	0.9300	C17—C18	1.3935 (11)
C3—C4	1.3906 (13)	C17—H17A	0.9300
C3—H3A	0.9300	C18—H18A	0.9300
C8—S1—C9	96.96 (4)	N3—C8—S1	120.03 (5)
N5—O1—C12	111.40 (5)	C10—C9—S1	111.37 (5)
C7—N1—N2	115.29 (6)	C10—C9—H9A	109.4
C8—N2—N1	110.58 (6)	S1—C9—H9A	109.4
C8—N3—N4	125.97 (6)	C10—C9—H9B	109.4
C8—N3—H1N3	115.9 (11)	S1—C9—H9B	109.4
N4—N3—H1N3	111.4 (10)	H9A—C9—H9B	108.0
C10—N4—N3	118.01 (6)	N4—C10—C11	115.69 (6)
N6—N5—O1	103.91 (5)	N4—C10—C9	122.87 (6)
N5—N6—C11	115.66 (6)	C11—C10—C9	121.45 (6)
N5—N6—C13	118.02 (6)	N6—C11—C12	105.42 (6)
C11—N6—C13	126.28 (6)	N6—C11—C10	125.08 (6)
C2—C1—C6	120.13 (7)	C12—C11—C10	129.33 (6)
C2—C1—H1A	119.9	O2—C12—O1	120.16 (6)
C6—C1—H1A	119.9	O2—C12—C11	136.18 (7)
C1—C2—C3	120.37 (8)	O1—C12—C11	103.61 (5)
C1—C2—H2A	119.8	C14—C13—C18	122.93 (6)
C3—C2—H2A	119.8	C14—C13—N6	119.23 (6)
C4—C3—C2	120.01 (8)	C18—C13—N6	117.80 (6)
C4—C3—H3A	120.0	C13—C14—C15	118.00 (7)
C2—C3—H3A	120.0	C13—C14—H14A	121.0
C3—C4—C5	119.76 (8)	C15—C14—H14A	121.0
C3—C4—H4A	120.1	C16—C15—C14	120.34 (7)
C5—C4—H4A	120.1	C16—C15—H15A	119.8
C4—C5—C6	120.62 (7)	C14—C15—H15A	119.8
C4—C5—H5A	119.7	C15—C16—C17	120.51 (7)
C6—C5—H5A	119.7	C15—C16—H16A	119.7
C5—C6—C1	119.11 (7)	C17—C16—H16A	119.7
C5—C6—C7	119.85 (7)	C18—C17—C16	119.99 (7)
C1—C6—C7	121.04 (7)	C18—C17—H17A	120.0
N1—C7—C6	119.76 (6)	C16—C17—H17A	120.0
N1—C7—H7A	120.1	C13—C18—C17	118.21 (7)
C6—C7—H7A	120.1	C13—C18—H18A	120.9
N2—C8—N3	118.27 (6)	C17—C18—H18A	120.9
N2—C8—S1	121.63 (5)
C7—N1—N2—C8	−173.31 (7)	N5—N6—C11—C12	0.31 (8)
C8—N3—N4—C10	−33.94 (10)	C13—N6—C11—C12	178.09 (6)
C12—O1—N5—N6	0.31 (8)	N5—N6—C11—C10	175.83 (7)
O1—N5—N6—C11	−0.39 (8)	C13—N6—C11—C10	−6.39 (11)
O1—N5—N6—C13	−178.36 (6)	N4—C10—C11—N6	145.60 (7)
C6—C1—C2—C3	1.12 (12)	C9—C10—C11—N6	−34.74 (11)
C1—C2—C3—C4	−0.80 (13)	N4—C10—C11—C12	−39.98 (11)
C2—C3—C4—C5	−0.21 (12)	C9—C10—C11—C12	139.68 (8)
C3—C4—C5—C6	0.90 (12)	N5—O1—C12—O2	−177.78 (7)
C4—C5—C6—C1	−0.58 (11)	N5—O1—C12—C11	−0.14 (8)
C4—C5—C6—C7	−179.42 (7)	N6—C11—C12—O2	176.97 (9)
C2—C1—C6—C5	−0.43 (11)	C10—C11—C12—O2	1.70 (14)
C2—C1—C6—C7	178.40 (7)	N6—C11—C12—O1	−0.09 (7)
N2—N1—C7—C6	−177.89 (6)	C10—C11—C12—O1	−175.35 (7)
C5—C6—C7—N1	−176.39 (7)	N5—N6—C13—C14	−62.37 (9)
C1—C6—C7—N1	4.79 (11)	C11—N6—C13—C14	119.90 (8)
N1—N2—C8—N3	−176.40 (6)	N5—N6—C13—C18	119.82 (7)
N1—N2—C8—S1	6.57 (9)	C11—N6—C13—C18	−57.91 (10)
N4—N3—C8—N2	−156.39 (7)	C18—C13—C14—C15	1.16 (11)
N4—N3—C8—S1	20.70 (10)	N6—C13—C14—C15	−176.54 (6)
C9—S1—C8—N2	−164.38 (6)	C13—C14—C15—C16	−0.22 (11)
C9—S1—C8—N3	18.64 (6)	C14—C15—C16—C17	−0.92 (12)
C8—S1—C9—C10	−45.98 (6)	C15—C16—C17—C18	1.17 (12)
N3—N4—C10—C11	175.86 (6)	C14—C13—C18—C17	−0.91 (11)
N3—N4—C10—C9	−3.80 (11)	N6—C13—C18—C17	176.81 (7)
S1—C9—C10—N4	45.22 (9)	C16—C17—C18—C13	−0.27 (12)
S1—C9—C10—C11	−134.42 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N2i	0.852 (15)	2.015 (15)	2.8664 (9)	178.3 (11)
C14—H14A···O2ii	0.93	2.58	3.2303 (10)	127
C15—H15A···O2iii	0.93	2.51	3.2391 (9)	136
C18—H18A···S1iv	0.93	2.84	3.7061 (8)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N2i	0.852 (15)	2.015 (15)	2.8664 (9)	178.3 (11)
C14—H14A⋯O2ii	0.93	2.58	3.2303 (10)	127
C15—H15A⋯O2iii	0.93	2.51	3.2391 (9)	136
C18—H18A⋯S1iv	0.93	2.84	3.7061 (8)	155

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