4-Formyl-3-p-tolyl-sydnone.

In the title compound, C(10)H(8)N(2)O(3), the oxadiazole ring is essentially planar, with a maximum deviation of 0.006 (1) Å for the two-connected N atom. The mean planes through the aldehyde unit and the methyl-substituted phenyl ring make inter-planar angles of 13.60 (9) and 59.69 (4)°, respectively, with the oxadiazole ring. In the crystal structure, adjacent mol-ecules are inter-connected into a two-dimensional array parallel to (100) by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to and applications of sydnone compounds, see: Hedge et al. (2008 ▶); Rai et al. (2008 ▶). For related sydnone structures, see: Baker & Ollis (1957 ▶); Grossie et al. (2009 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H8N2O3

M = 204.18

Monoclinic,

a = 10.5663 (4) Å

b = 10.4088 (3) Å

c = 8.9630 (3) Å

β = 108.222 (1)°

V = 936.34 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.71 × 0.30 × 0.19 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.926, T max = 0.980

14437 measured reflections

4906 independent reflections

4091 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.132

S = 1.07

4906 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.31 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/S1600536810016417/fj2294sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016417/fj2294Isup2.hkl

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

C10H8N2O3	F(000) = 424
Mr = 204.18	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6788 reflections
a = 10.5663 (4) Å	θ = 2.8–38.9°
b = 10.4088 (3) Å	µ = 0.11 mm−1
c = 8.9630 (3) Å	T = 100 K
β = 108.222 (1)°	Block, brown
V = 936.34 (5) Å3	0.71 × 0.30 × 0.19 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4906 independent reflections
Radiation source: fine-focus sealed tube	4091 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 37.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −18→18
Tmin = 0.926, Tmax = 0.980	k = −17→17
14437 measured reflections	l = −15→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0747P)2 + 0.1421P] where P = (Fo2 + 2Fc2)/3
4906 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.31 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	0.34006 (6)	0.22147 (5)	0.96639 (6)	0.01912 (11)
O2	0.26550 (6)	0.39559 (5)	1.06918 (7)	0.02245 (12)
O3	0.53489 (6)	0.55203 (5)	1.23353 (7)	0.02190 (12)
N1	0.54958 (6)	0.24689 (5)	1.05402 (6)	0.01524 (10)
N2	0.45929 (7)	0.17063 (6)	0.96707 (7)	0.01825 (11)
C1	0.76823 (8)	0.30000 (7)	1.03217 (9)	0.02080 (13)
H1A	0.7346	0.3773	0.9839	0.025*
C2	0.90126 (8)	0.26687 (7)	1.05976 (10)	0.02297 (14)
H2A	0.9571	0.3228	1.0289	0.028*
C3	0.95243 (8)	0.15115 (7)	1.13297 (9)	0.02082 (13)
C4	0.86671 (8)	0.06713 (7)	1.17625 (9)	0.02117 (13)
H4A	0.8996	−0.0106	1.2238	0.025*
C5	0.73342 (8)	0.09745 (6)	1.14961 (8)	0.01803 (12)
H5A	0.6768	0.0411	1.1783	0.022*
C6	0.68736 (7)	0.21424 (6)	1.07890 (7)	0.01561 (11)
C7	0.35989 (7)	0.33640 (6)	1.05605 (8)	0.01719 (12)
C8	0.50088 (7)	0.34990 (6)	1.11215 (8)	0.01566 (11)
C9	0.58136 (8)	0.44999 (6)	1.20780 (8)	0.01744 (12)
H9A	0.6724	0.4362	1.2517	0.021*
C10	1.09685 (9)	0.11710 (10)	1.16471 (12)	0.03014 (17)
H10D	1.1460	0.1928	1.1562	0.045*
H10A	1.1048	0.0545	1.0895	0.045*
H10B	1.1319	0.0823	1.2687	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0194 (2)	0.0159 (2)	0.0216 (2)	0.00027 (17)	0.00558 (19)	−0.00320 (16)
O2	0.0212 (3)	0.0188 (2)	0.0285 (3)	0.00347 (18)	0.0094 (2)	−0.00196 (18)
O3	0.0306 (3)	0.0144 (2)	0.0250 (2)	−0.00230 (19)	0.0148 (2)	−0.00363 (17)
N1	0.0194 (3)	0.01228 (19)	0.0155 (2)	−0.00027 (17)	0.00755 (19)	−0.00047 (15)
N2	0.0206 (3)	0.0153 (2)	0.0194 (2)	−0.00021 (19)	0.0070 (2)	−0.00313 (17)
C1	0.0255 (3)	0.0152 (2)	0.0263 (3)	−0.0009 (2)	0.0148 (3)	0.0028 (2)
C2	0.0243 (3)	0.0202 (3)	0.0294 (3)	−0.0039 (2)	0.0157 (3)	−0.0007 (2)
C3	0.0195 (3)	0.0230 (3)	0.0216 (3)	−0.0007 (2)	0.0089 (2)	−0.0034 (2)
C4	0.0220 (3)	0.0192 (3)	0.0237 (3)	0.0025 (2)	0.0091 (3)	0.0025 (2)
C5	0.0207 (3)	0.0143 (2)	0.0211 (3)	0.0000 (2)	0.0095 (2)	0.00184 (19)
C6	0.0186 (3)	0.0133 (2)	0.0172 (2)	−0.00044 (19)	0.0088 (2)	−0.00029 (17)
C7	0.0210 (3)	0.0134 (2)	0.0179 (2)	0.0007 (2)	0.0072 (2)	−0.00046 (18)
C8	0.0195 (3)	0.0127 (2)	0.0166 (2)	0.0000 (2)	0.0083 (2)	−0.00152 (17)
C9	0.0220 (3)	0.0149 (2)	0.0178 (2)	−0.0033 (2)	0.0097 (2)	−0.00218 (19)
C10	0.0195 (3)	0.0387 (4)	0.0328 (4)	0.0012 (3)	0.0091 (3)	−0.0044 (3)

O1—N2	1.3647 (8)	C3—C4	1.3983 (11)
O1—C7	1.4197 (8)	C3—C10	1.5046 (12)
O2—C7	1.2089 (9)	C4—C5	1.3893 (11)
O3—C9	1.2220 (9)	C4—H4A	0.9300
N1—N2	1.2971 (8)	C5—C6	1.3870 (9)
N1—C8	1.3615 (8)	C5—H5A	0.9300
N1—C6	1.4428 (9)	C7—C8	1.4225 (10)
C1—C6	1.3878 (9)	C8—C9	1.4448 (9)
C1—C2	1.3924 (11)	C9—H9A	0.9300
C1—H1A	0.9300	C10—H10D	0.9600
C2—C3	1.3971 (11)	C10—H10A	0.9600
C2—H2A	0.9300	C10—H10B	0.9600
N2—O1—C7	110.58 (5)	C4—C5—H5A	121.0
N2—N1—C8	114.64 (6)	C5—C6—C1	122.72 (7)
N2—N1—C6	117.76 (5)	C5—C6—N1	118.03 (6)
C8—N1—C6	127.60 (6)	C1—C6—N1	119.25 (6)
N1—N2—O1	105.66 (5)	O2—C7—O1	120.29 (7)
C6—C1—C2	118.02 (7)	O2—C7—C8	136.05 (6)
C6—C1—H1A	121.0	O1—C7—C8	103.66 (5)
C2—C1—H1A	121.0	N1—C8—C7	105.44 (6)
C1—C2—C3	121.19 (7)	N1—C8—C9	124.90 (6)
C1—C2—H2A	119.4	C7—C8—C9	129.64 (6)
C3—C2—H2A	119.4	O3—C9—C8	122.82 (7)
C2—C3—C4	118.71 (7)	O3—C9—H9A	118.6
C2—C3—C10	120.83 (7)	C8—C9—H9A	118.6
C4—C3—C10	120.45 (7)	C3—C10—H10D	109.5
C5—C4—C3	121.34 (7)	C3—C10—H10A	109.5
C5—C4—H4A	119.3	H10D—C10—H10A	109.5
C3—C4—H4A	119.3	C3—C10—H10B	109.5
C6—C5—C4	118.01 (6)	H10D—C10—H10B	109.5
C6—C5—H5A	121.0	H10A—C10—H10B	109.5
C8—N1—N2—O1	−1.23 (7)	N2—N1—C6—C1	120.44 (7)
C6—N1—N2—O1	178.51 (5)	C8—N1—C6—C1	−59.85 (9)
C7—O1—N2—N1	1.09 (7)	N2—O1—C7—O2	179.97 (6)
C6—C1—C2—C3	−0.31 (11)	N2—O1—C7—C8	−0.58 (7)
C1—C2—C3—C4	1.07 (12)	N2—N1—C8—C7	0.88 (7)
C1—C2—C3—C10	−178.99 (8)	C6—N1—C8—C7	−178.84 (6)
C2—C3—C4—C5	−0.81 (11)	N2—N1—C8—C9	−178.07 (6)
C10—C3—C4—C5	179.25 (7)	C6—N1—C8—C9	2.22 (10)
C3—C4—C5—C6	−0.19 (11)	O2—C7—C8—N1	179.18 (8)
C4—C5—C6—C1	1.01 (11)	O1—C7—C8—N1	−0.13 (7)
C4—C5—C6—N1	−178.80 (6)	O2—C7—C8—C9	−1.94 (13)
C2—C1—C6—C5	−0.76 (11)	O1—C7—C8—C9	178.74 (6)
C2—C1—C6—N1	179.05 (6)	N1—C8—C9—O3	166.06 (6)
N2—N1—C6—C5	−59.74 (8)	C7—C8—C9—O3	−12.62 (11)
C8—N1—C6—C5	119.96 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.93	2.41	3.2847 (9)	156
C5—H5A···O3ii	0.93	2.60	3.3489 (11)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.93	2.41	3.2847 (9)	156
C5—H5A⋯O3ii	0.93	2.60	3.3489 (11)	138

Symmetry codes: (i) ; (ii) .