2-[(6-Nitro-1,3-benzodioxol-5-yl)methyl-idene]malononitrile.

In the title compound, C(11)H(5)N(3)O(4), the nitro group is rotated by 29.91 (16)° out of the plane of the adjacent aryl ring. The 1,3-benzodioxole ring is nearly planar, with a maximium deviation of 0.0562 (10) Å. The dioxolene ring adopts an envelope conformation on the O-C-O C atom. In the crystal, mol-ecules are linked via C-H⋯O inter-actions, resulting in R(2) (2)(6) and R(2) (2)(12) graph-set motifs.

Related literature

For applications of malononitrile derivatives, see: Brimblecombe et al. (1972 ▶). For related structure, see: Loghmani–Khouzani et al. (2009 ▶). For comparison of mol­ecular dimensions, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For graph–set motif notations, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H5N3O4

M = 243.18

Triclinic,

a = 7.0953 (2) Å

b = 8.8847 (3) Å

c = 9.2212 (3) Å

α = 84.470 (2)°

β = 67.634 (2)°

γ = 78.874 (2)°

V = 527.30 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.30 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

13806 measured reflections

3494 independent reflections

2700 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.142

S = 1.03

3494 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al. 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049816/rk2314sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049816/rk2314Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049816/rk2314Isup3.cml

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

C11H5N3O4	Z = 2
Mr = 243.18	F(000) = 248
Triclinic, P1	Dx = 1.532 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0953 (2) Å	Cell parameters from 3494 reflections
b = 8.8847 (3) Å	θ = 1.0–31.6°
c = 9.2212 (3) Å	µ = 0.12 mm−1
α = 84.470 (2)°	T = 295 K
β = 67.634 (2)°	Block, yellow
γ = 78.874 (2)°	0.30 × 0.28 × 0.25 mm
V = 527.30 (3) Å3

Bruker Kappa APEXII CCD diffractometer	2700 reflections with I > 2σ(I)
Radiation source: fine–focus sealed tube	Rint = 0.025
graphite	θmax = 31.6°, θmin = 2.3°
ω scans	h = −10→10
13806 measured reflections	k = −12→12
3494 independent reflections	l = −13→13

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0779P)2 + 0.0833P] where P = (Fo2 + 2Fc2)/3
3494 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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 > σ(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
C1	0.1956 (2)	0.45131 (18)	0.79855 (15)	0.0499 (3)
H1A	0.2553	0.3433	0.7969	0.060*
H1B	0.2182	0.4995	0.8792	0.060*
C2	0.13009 (16)	0.60560 (13)	0.61230 (12)	0.0335 (2)
C3	0.13982 (17)	0.70725 (13)	0.48999 (12)	0.0345 (2)
H3	0.2663	0.7286	0.4190	0.041*
C4	−0.04642 (16)	0.77900 (12)	0.47404 (12)	0.0309 (2)
C5	−0.23081 (16)	0.74097 (12)	0.58573 (13)	0.0331 (2)
C6	−0.24088 (17)	0.63890 (13)	0.71134 (13)	0.0373 (2)
H6	−0.3660	0.6171	0.7842	0.045*
C7	−0.05588 (18)	0.57270 (13)	0.72113 (12)	0.0351 (2)
C8	−0.04545 (17)	0.90159 (12)	0.35650 (13)	0.0347 (2)
H8	−0.1612	0.9786	0.3818	0.042*
C9	0.10476 (19)	0.91503 (13)	0.21576 (14)	0.0386 (2)
C10	0.0900 (2)	1.05218 (15)	0.12130 (16)	0.0478 (3)
C11	0.2814 (2)	0.79907 (17)	0.14691 (15)	0.0491 (3)
N1	−0.42888 (15)	0.80802 (11)	0.57275 (13)	0.0417 (2)
N2	0.0804 (3)	1.16093 (16)	0.04706 (18)	0.0707 (4)
N3	0.4220 (2)	0.7081 (2)	0.09043 (17)	0.0760 (5)
O1	−0.02108 (14)	0.46924 (11)	0.82958 (10)	0.0483 (2)
O2	0.28869 (13)	0.52328 (11)	0.64860 (10)	0.0457 (2)
O3	−0.43369 (15)	0.84163 (11)	0.44228 (12)	0.0507 (3)
O4	−0.58153 (15)	0.82535 (14)	0.69255 (14)	0.0674 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0424 (7)	0.0658 (8)	0.0332 (6)	0.0027 (6)	−0.0132 (5)	0.0108 (5)
C2	0.0307 (5)	0.0392 (5)	0.0288 (5)	−0.0007 (4)	−0.0115 (4)	−0.0001 (4)
C3	0.0298 (5)	0.0412 (5)	0.0304 (5)	−0.0058 (4)	−0.0101 (4)	0.0036 (4)
C4	0.0308 (5)	0.0307 (5)	0.0304 (5)	−0.0039 (4)	−0.0114 (4)	0.0004 (4)
C5	0.0279 (5)	0.0323 (5)	0.0367 (5)	−0.0011 (4)	−0.0111 (4)	−0.0009 (4)
C6	0.0306 (5)	0.0396 (6)	0.0343 (5)	−0.0040 (4)	−0.0056 (4)	0.0033 (4)
C7	0.0364 (5)	0.0372 (5)	0.0272 (5)	−0.0026 (4)	−0.0094 (4)	0.0024 (4)
C8	0.0349 (5)	0.0324 (5)	0.0388 (5)	−0.0057 (4)	−0.0167 (4)	0.0030 (4)
C9	0.0410 (6)	0.0401 (6)	0.0386 (6)	−0.0114 (5)	−0.0190 (5)	0.0086 (4)
C10	0.0602 (8)	0.0460 (7)	0.0449 (7)	−0.0211 (6)	−0.0253 (6)	0.0122 (5)
C11	0.0415 (7)	0.0632 (8)	0.0361 (6)	−0.0077 (6)	−0.0108 (5)	0.0109 (5)
N1	0.0309 (5)	0.0360 (5)	0.0550 (6)	−0.0031 (4)	−0.0153 (4)	0.0051 (4)
N2	0.1052 (13)	0.0544 (7)	0.0656 (9)	−0.0313 (8)	−0.0436 (9)	0.0243 (6)
N3	0.0539 (8)	0.0989 (12)	0.0516 (8)	0.0105 (8)	−0.0062 (6)	0.0049 (8)
O1	0.0414 (5)	0.0590 (6)	0.0362 (4)	−0.0034 (4)	−0.0116 (4)	0.0164 (4)
O2	0.0336 (4)	0.0603 (6)	0.0375 (4)	0.0003 (4)	−0.0141 (3)	0.0121 (4)
O3	0.0472 (5)	0.0499 (5)	0.0639 (6)	−0.0064 (4)	−0.0329 (5)	0.0056 (4)
O4	0.0323 (5)	0.0746 (7)	0.0705 (7)	0.0072 (5)	−0.0034 (5)	0.0157 (6)

C1—O1	1.4319 (17)	C5—N1	1.4614 (14)
C1—O2	1.4334 (15)	C6—C7	1.3635 (15)
C1—H1A	0.9700	C6—H6	0.9300
C1—H1B	0.9700	C7—O1	1.3525 (13)
C2—O2	1.3547 (13)	C8—C9	1.3420 (16)
C2—C3	1.3641 (15)	C8—H8	0.9300
C2—C7	1.3850 (16)	C9—C11	1.4342 (19)
C3—C4	1.4068 (14)	C9—C10	1.4388 (16)
C3—H3	0.9300	C10—N2	1.1355 (18)
C4—C5	1.4016 (15)	C11—N3	1.138 (2)
C4—C8	1.4597 (14)	N1—O4	1.2145 (15)
C5—C6	1.3887 (15)	N1—O3	1.2230 (14)
O1—C1—O2	107.04 (9)	C7—C6—H6	122.1
O1—C1—H1A	110.3	C5—C6—H6	122.1
O2—C1—H1A	110.3	O1—C7—C6	128.09 (10)
O1—C1—H1B	110.3	O1—C7—C2	110.03 (10)
O2—C1—H1B	110.3	C6—C7—C2	121.87 (10)
H1A—C1—H1B	108.6	C9—C8—C4	126.91 (10)
O2—C2—C3	128.07 (10)	C9—C8—H8	116.5
O2—C2—C7	109.65 (9)	C4—C8—H8	116.5
C3—C2—C7	122.28 (10)	C8—C9—C11	124.80 (11)
C2—C3—C4	118.30 (10)	C8—C9—C10	119.43 (12)
C2—C3—H3	120.9	C11—C9—C10	115.74 (11)
C4—C3—H3	120.9	N2—C10—C9	179.14 (15)
C5—C4—C3	117.50 (9)	N3—C11—C9	179.09 (15)
C5—C4—C8	121.96 (9)	O4—N1—O3	123.24 (11)
C3—C4—C8	120.12 (9)	O4—N1—C5	118.09 (11)
C6—C5—C4	124.20 (10)	O3—N1—C5	118.67 (10)
C6—C5—N1	115.70 (10)	C7—O1—C1	105.81 (9)
C4—C5—N1	120.10 (10)	C2—O2—C1	105.89 (9)
C7—C6—C5	115.83 (10)
O2—C2—C3—C4	179.32 (11)	C3—C2—C7—C6	0.79 (18)
C7—C2—C3—C4	−0.78 (17)	C5—C4—C8—C9	−154.85 (11)
C2—C3—C4—C5	0.01 (16)	C3—C4—C8—C9	32.75 (16)
C2—C3—C4—C8	172.74 (10)	C4—C8—C9—C11	8.72 (19)
C3—C4—C5—C6	0.80 (17)	C4—C8—C9—C10	−173.31 (10)
C8—C4—C5—C6	−171.78 (10)	C6—C5—N1—O4	29.91 (16)
C3—C4—C5—N1	−178.10 (9)	C4—C5—N1—O4	−151.10 (12)
C8—C4—C5—N1	9.32 (16)	C6—C5—N1—O3	−148.95 (11)
C4—C5—C6—C7	−0.81 (17)	C4—C5—N1—O3	30.04 (15)
N1—C5—C6—C7	178.14 (10)	C6—C7—O1—C1	−173.03 (12)
C5—C6—C7—O1	−179.34 (11)	C2—C7—O1—C1	7.55 (14)
C5—C6—C7—C2	0.01 (17)	O2—C1—O1—C7	−12.15 (14)
O2—C2—C7—O1	0.17 (14)	C3—C2—O2—C1	172.11 (12)
C3—C2—C7—O1	−179.75 (10)	C7—C2—O2—C1	−7.80 (14)
O2—C2—C7—C6	−179.29 (10)	O1—C1—O2—C2	12.26 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1i	0.97	2.53	3.2692 (16)	133
C8—H8···O4ii	0.93	2.52	3.3640 (17)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1i	0.97	2.53	3.2692 (16)	133
C8—H8⋯O4ii	0.93	2.52	3.3640 (17)	152

Symmetry codes: (i) ; (ii) .