3-(p-Anis-yl)sydnone.

IN THE TITLE SYDNONE COMPOUND [SYSTEMATIC NAME: 3-(4-meth-oxy-phen-yl)-1,2,3-oxadiazol-3-ium-5-olate], C(9)H(8)N(2)O(3), the essentially planar oxadiazole ring [maximum deviation = 0.005 (1) Å] is inclined at a dihedral angle of 30.32 (8)° with respect to the benzene ring. In the crystal, adjacent mol-ecules are inter-connected by inter-molecular C-H⋯O hydrogen bonds into sheets lying parallel to (100). Weak inter-molecular π-π inter-actions [centroid-centroid distance = 3.5812 (8) Å] further stabilize the crystal packing.

Related literature

For general background to and applications of the title sydnone compound, see: Hegde et al. (2008 ▶); Kalluraya & Rahiman (1997 ▶); Kalluraya et al. (2002 ▶); Rai et al. (2008 ▶). For closely related sydnone structures, see: Goh et al. (2010a ▶,b ▶,c ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C9H8N2O3

M = 192.17

Orthorhombic,

a = 7.0505 (2) Å

b = 9.8220 (3) Å

c = 12.0934 (3) Å

V = 837.47 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.56 × 0.15 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.938, T max = 0.984

7384 measured reflections

1760 independent reflections

1577 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.100

S = 1.06

1760 reflections

159 parameters

All H-atom parameters refined

Δρmax = 0.32 e Å−3

Δρmin = −0.26 e Å−3

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; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047422/rz2524sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047422/rz2524Isup2.hkl

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

C9H8N2O3	F(000) = 400
Mr = 192.17	Dx = 1.524 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2851 reflections
a = 7.0505 (2) Å	θ = 3.4–32.4°
b = 9.8220 (3) Å	µ = 0.12 mm−1
c = 12.0934 (3) Å	T = 100 K
V = 837.47 (4) Å3	Needle, yellow
Z = 4	0.56 × 0.15 × 0.14 mm

Bruker SMART APEXII CCD area-detector diffractometer	1760 independent reflections
Radiation source: fine-focus sealed tube	1577 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 32.7°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.938, Tmax = 0.984	k = −14→14
7384 measured reflections	l = −18→18

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.0718P] where P = (Fo2 + 2Fc2)/3
1760 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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
O1	0.08268 (18)	0.95246 (11)	0.72517 (9)	0.0204 (2)
O2	0.15734 (19)	0.83477 (13)	0.88211 (9)	0.0252 (3)
O3	0.12932 (18)	0.57288 (10)	0.18145 (8)	0.0199 (2)
N1	0.0695 (2)	0.92968 (13)	0.61277 (11)	0.0199 (3)
N2	0.11891 (19)	0.80122 (12)	0.60181 (10)	0.0152 (2)
C1	0.1632 (2)	0.82919 (14)	0.40336 (11)	0.0157 (2)
C2	0.1665 (2)	0.77417 (15)	0.29712 (11)	0.0158 (3)
C3	0.1284 (2)	0.63583 (15)	0.28173 (12)	0.0160 (3)
C4	0.0868 (2)	0.55302 (15)	0.37253 (13)	0.0179 (3)
C5	0.0829 (2)	0.60641 (15)	0.47811 (12)	0.0165 (3)
C6	0.1211 (2)	0.74504 (16)	0.49222 (12)	0.0145 (2)
C7	0.1622 (2)	0.73661 (15)	0.69641 (12)	0.0173 (3)
C8	0.1394 (2)	0.83234 (16)	0.78201 (12)	0.0186 (3)
C9	0.1403 (3)	0.65840 (16)	0.08473 (12)	0.0205 (3)
H1A	0.192 (3)	0.928 (2)	0.4147 (15)	0.019 (5)*
H2A	0.194 (3)	0.831 (2)	0.2340 (16)	0.024 (5)*
H4A	0.070 (3)	0.457 (2)	0.3623 (16)	0.025 (5)*
H5A	0.047 (3)	0.5524 (19)	0.5411 (15)	0.015 (5)*
H7A	0.203 (3)	0.641 (2)	0.6995 (17)	0.026 (5)*
H9A	0.124 (3)	0.603 (2)	0.0190 (16)	0.020 (5)*
H9B	0.040 (3)	0.723 (2)	0.0852 (16)	0.023 (5)*
H9C	0.262 (4)	0.708 (3)	0.0800 (19)	0.041 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0255 (5)	0.0180 (5)	0.0179 (5)	0.0014 (5)	0.0003 (5)	−0.0028 (4)
O2	0.0316 (6)	0.0267 (5)	0.0172 (5)	−0.0033 (6)	−0.0014 (5)	−0.0011 (4)
O3	0.0290 (6)	0.0155 (5)	0.0151 (5)	0.0016 (4)	−0.0015 (4)	−0.0013 (3)
N1	0.0258 (6)	0.0151 (5)	0.0188 (6)	0.0035 (5)	−0.0003 (5)	−0.0016 (4)
N2	0.0152 (5)	0.0141 (5)	0.0163 (5)	−0.0003 (4)	−0.0002 (4)	0.0006 (4)
C1	0.0168 (6)	0.0136 (5)	0.0167 (6)	−0.0008 (5)	−0.0016 (5)	0.0004 (4)
C2	0.0168 (6)	0.0136 (6)	0.0169 (6)	−0.0011 (5)	−0.0010 (5)	0.0016 (4)
C3	0.0154 (6)	0.0158 (6)	0.0169 (6)	0.0007 (5)	−0.0016 (5)	−0.0013 (4)
C4	0.0213 (7)	0.0130 (5)	0.0195 (6)	−0.0017 (5)	0.0001 (5)	0.0000 (5)
C5	0.0166 (6)	0.0138 (5)	0.0191 (6)	−0.0013 (5)	0.0004 (6)	0.0010 (5)
C6	0.0138 (6)	0.0142 (5)	0.0154 (5)	0.0001 (5)	0.0004 (5)	−0.0003 (4)
C7	0.0190 (6)	0.0167 (6)	0.0164 (6)	−0.0002 (5)	−0.0007 (5)	0.0016 (5)
C8	0.0176 (6)	0.0188 (6)	0.0192 (6)	−0.0014 (6)	−0.0003 (6)	0.0006 (5)
C9	0.0256 (7)	0.0200 (6)	0.0159 (6)	0.0019 (6)	−0.0014 (6)	−0.0002 (5)

O1—N1	1.3807 (16)	C2—H2A	0.97 (2)
O1—C8	1.4227 (19)	C3—C4	1.398 (2)
O2—C8	1.2174 (18)	C4—C5	1.381 (2)
O3—C3	1.3613 (17)	C4—H4A	0.95 (2)
O3—C9	1.4421 (18)	C5—C6	1.398 (2)
N1—N2	1.3158 (16)	C5—H5A	0.961 (19)
N2—C7	1.3434 (17)	C7—C8	1.408 (2)
N2—C6	1.4356 (18)	C7—H7A	0.98 (2)
C1—C6	1.388 (2)	C9—H9A	0.97 (2)
C1—C2	1.3940 (19)	C9—H9B	0.95 (2)
C1—H1A	1.00 (2)	C9—H9C	0.99 (3)
C2—C3	1.3976 (19)
N1—O1—C8	111.11 (12)	C4—C5—C6	118.61 (13)
C3—O3—C9	117.27 (11)	C4—C5—H5A	121.9 (11)
N2—N1—O1	103.69 (12)	C6—C5—H5A	119.4 (11)
N1—N2—C7	115.30 (12)	C1—C6—C5	121.77 (14)
N1—N2—C6	117.68 (12)	C1—C6—N2	119.22 (13)
C7—N2—C6	127.02 (12)	C5—C6—N2	119.00 (13)
C6—C1—C2	119.11 (13)	N2—C7—C8	106.54 (13)
C6—C1—H1A	121.0 (11)	N2—C7—H7A	123.4 (12)
C2—C1—H1A	119.9 (11)	C8—C7—H7A	130.1 (12)
C1—C2—C3	119.76 (13)	O2—C8—C7	137.09 (16)
C1—C2—H2A	120.5 (13)	O2—C8—O1	119.56 (14)
C3—C2—H2A	119.8 (13)	C7—C8—O1	103.34 (12)
O3—C3—C4	115.89 (13)	O3—C9—H9A	109.4 (12)
O3—C3—C2	124.01 (13)	O3—C9—H9B	110.2 (12)
C4—C3—C2	120.10 (13)	H9A—C9—H9B	107.0 (17)
C5—C4—C3	120.65 (13)	O3—C9—H9C	112.3 (15)
C5—C4—H4A	119.4 (12)	H9A—C9—H9C	109.3 (18)
C3—C4—H4A	119.8 (12)	H9B—C9—H9C	108.5 (19)
C8—O1—N1—N2	−0.84 (16)	C4—C5—C6—C1	−0.2 (2)
O1—N1—N2—C7	0.46 (17)	C4—C5—C6—N2	−179.47 (14)
O1—N1—N2—C6	−179.58 (12)	N1—N2—C6—C1	30.90 (19)
C6—C1—C2—C3	−0.2 (2)	C7—N2—C6—C1	−149.14 (15)
C9—O3—C3—C4	169.99 (14)	N1—N2—C6—C5	−149.86 (15)
C9—O3—C3—C2	−10.3 (2)	C7—N2—C6—C5	30.1 (2)
C1—C2—C3—O3	−179.64 (13)	N1—N2—C7—C8	0.09 (18)
C1—C2—C3—C4	0.0 (2)	C6—N2—C7—C8	−179.87 (13)
O3—C3—C4—C5	179.72 (14)	N2—C7—C8—O2	−179.70 (19)
C2—C3—C4—C5	0.0 (2)	N2—C7—C8—O1	−0.58 (16)
C3—C4—C5—C6	0.1 (2)	N1—O1—C8—O2	−179.79 (14)
C2—C1—C6—C5	0.3 (2)	N1—O1—C8—C7	0.89 (17)
C2—C1—C6—N2	179.53 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	1.00 (2)	2.59 (2)	3.5441 (19)	159.1 (15)
C7—H7A···O3ii	0.98 (2)	2.42 (2)	3.3814 (18)	165.7 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	1.00 (2)	2.59 (2)	3.5441 (19)	159.1 (15)
C7—H7A⋯O3ii	0.98 (2)	2.42 (2)	3.3814 (18)	165.7 (17)

Symmetry codes: (i) ; (ii) .