Methyl (E)-2-cyano-3-(6-nitro-1,3-benzodioxol-5-yl)acrylate.

In the title compound, C(12)H(8)N(2)O(6), the 1,3-benzodioxole ring system is essentially planar [maximum deviation = 0.036 (2) Å] and the nitro group is oriented at a dihedral angle of 15.4 (1)° with respect to its mean plane. In the crystal, moleucles are linked into C(8) [101] chains by C-H⋯O hydrogen bonds, and weak aromatic π-π stacking [centroid-centroid distance = 3.887 (1) Å] also occurs.

Related literature

For a related structure and background references, see: Karthikeyan et al. (2011 ▶); Loghmani-Khouzani et al. (2009 ▶).

Experimental

Crystal data

C12H8N2O6

M = 276.20

Monoclinic,

a = 10.8191 (9) Å

b = 7.3220 (6) Å

c = 15.4133 (13) Å

β = 91.691 (2)°

V = 1220.47 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.23 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.979

14190 measured reflections

3567 independent reflections

2286 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.129

S = 1.03

3567 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043164/hb6968sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043164/hb6968Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812043164/hb6968Isup3.cml

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

C12H8N2O6	F(000) = 568
Mr = 276.20	Dx = 1.503 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3589 reflections
a = 10.8191 (9) Å	θ = 2.3–30.1°
b = 7.3220 (6) Å	µ = 0.12 mm−1
c = 15.4133 (13) Å	T = 293 K
β = 91.691 (2)°	Block, colourless
V = 1220.47 (18) Å3	0.23 × 0.22 × 0.17 mm
Z = 4

Bruker APEXII CCD diffractometer	3567 independent reflections
Radiation source: fine-focus sealed tube	2286 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 30.1°, θmin = 2.3°
ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→10
Tmin = 0.972, Tmax = 0.979	l = −21→19
14190 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0569P)2 + 0.1956P] where P = (Fo2 + 2Fc2)/3
3567 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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
C1	0.34825 (14)	0.0705 (2)	0.14286 (9)	0.0415 (3)
H1	0.3194	0.0163	0.1929	0.050*
C2	0.44834 (14)	0.1836 (2)	0.14611 (9)	0.0408 (3)
C3	0.60882 (16)	0.3581 (3)	0.18676 (11)	0.0560 (4)
H3A	0.5974	0.4774	0.2126	0.067*
H3B	0.6912	0.3149	0.2026	0.067*
C4	0.49334 (13)	0.26561 (19)	0.07304 (10)	0.0395 (3)
C5	0.43953 (14)	0.2399 (2)	−0.00694 (9)	0.0406 (3)
H5	0.4697	0.2955	−0.0563	0.049*
C6	0.33678 (13)	0.12542 (19)	−0.01065 (8)	0.0372 (3)
C7	0.28993 (13)	0.03817 (19)	0.06181 (9)	0.0375 (3)
C8	0.18022 (14)	−0.0796 (2)	0.05853 (9)	0.0428 (3)
H8	0.1115	−0.0384	0.0266	0.051*
C9	0.17142 (13)	−0.2415 (2)	0.09786 (9)	0.0414 (3)
C10	0.05270 (16)	−0.3443 (2)	0.09545 (10)	0.0481 (4)
C11	−0.0446 (2)	−0.6111 (3)	0.14488 (14)	0.0865 (8)
H11A	−0.0937	−0.5637	0.1906	0.130*
H11B	−0.0215	−0.7349	0.1579	0.130*
H11C	−0.0917	−0.6077	0.0911	0.130*
C12	0.27569 (16)	−0.3259 (2)	0.14154 (11)	0.0484 (4)
N1	0.35768 (15)	−0.3935 (2)	0.17628 (12)	0.0710 (5)
N2	0.28260 (12)	0.09294 (19)	−0.09677 (8)	0.0472 (3)
O1	0.51784 (12)	0.23313 (16)	0.21683 (7)	0.0566 (3)
O2	0.59385 (11)	0.36932 (17)	0.09442 (7)	0.0549 (3)
O3	0.21209 (14)	−0.03492 (18)	−0.10801 (8)	0.0666 (4)
O4	0.31029 (14)	0.1961 (2)	−0.15503 (8)	0.0796 (5)
O5	−0.03967 (12)	−0.2902 (2)	0.06023 (9)	0.0704 (4)
O6	0.06541 (12)	−0.50122 (16)	0.13725 (8)	0.0589 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0503 (9)	0.0418 (8)	0.0322 (6)	−0.0033 (7)	0.0004 (6)	0.0053 (6)
C2	0.0479 (8)	0.0384 (8)	0.0357 (7)	0.0000 (6)	−0.0082 (6)	0.0024 (6)
C3	0.0527 (10)	0.0612 (10)	0.0530 (9)	−0.0109 (8)	−0.0154 (8)	0.0049 (8)
C4	0.0381 (7)	0.0362 (7)	0.0440 (7)	−0.0009 (6)	−0.0040 (6)	0.0060 (6)
C5	0.0440 (8)	0.0405 (7)	0.0374 (7)	0.0013 (6)	0.0008 (6)	0.0083 (6)
C6	0.0411 (7)	0.0374 (7)	0.0327 (6)	0.0029 (6)	−0.0050 (6)	0.0023 (6)
C7	0.0390 (7)	0.0346 (7)	0.0389 (7)	0.0005 (6)	−0.0001 (6)	0.0027 (6)
C8	0.0398 (8)	0.0483 (8)	0.0403 (7)	−0.0002 (7)	−0.0014 (6)	−0.0014 (6)
C9	0.0381 (7)	0.0464 (8)	0.0400 (7)	−0.0044 (6)	0.0054 (6)	−0.0008 (6)
C10	0.0468 (9)	0.0586 (10)	0.0395 (7)	−0.0135 (8)	0.0091 (7)	−0.0080 (7)
C11	0.0961 (16)	0.0936 (16)	0.0707 (13)	−0.0623 (14)	0.0181 (11)	−0.0093 (12)
C12	0.0437 (9)	0.0436 (8)	0.0584 (9)	−0.0069 (7)	0.0090 (7)	0.0084 (7)
N1	0.0541 (9)	0.0636 (10)	0.0951 (13)	0.0040 (8)	0.0009 (9)	0.0224 (9)
N2	0.0523 (8)	0.0526 (8)	0.0364 (6)	−0.0010 (7)	−0.0047 (6)	0.0011 (6)
O1	0.0685 (8)	0.0590 (7)	0.0412 (6)	−0.0174 (6)	−0.0175 (5)	0.0084 (5)
O2	0.0505 (7)	0.0605 (7)	0.0529 (6)	−0.0165 (6)	−0.0125 (5)	0.0109 (6)
O3	0.0882 (9)	0.0585 (8)	0.0520 (7)	−0.0219 (7)	−0.0152 (6)	−0.0052 (6)
O4	0.0919 (10)	0.1096 (12)	0.0367 (6)	−0.0364 (9)	−0.0120 (6)	0.0199 (7)
O5	0.0437 (7)	0.0963 (10)	0.0708 (8)	−0.0157 (7)	−0.0048 (6)	0.0024 (7)
O6	0.0640 (8)	0.0560 (7)	0.0575 (7)	−0.0254 (6)	0.0143 (6)	−0.0048 (6)

C1—C2	1.363 (2)	C7—C8	1.467 (2)
C1—C7	1.403 (2)	C8—C9	1.336 (2)
C1—H1	0.9300	C8—H8	0.9300
C2—O1	1.3553 (17)	C9—C12	1.436 (2)
C2—C4	1.378 (2)	C9—C10	1.488 (2)
C3—O2	1.430 (2)	C10—O5	1.191 (2)
C3—O1	1.431 (2)	C10—O6	1.323 (2)
C3—H3A	0.9700	C11—O6	1.444 (2)
C3—H3B	0.9700	C11—H11A	0.9600
C4—O2	1.3589 (18)	C11—H11B	0.9600
C4—C5	1.361 (2)	C11—H11C	0.9600
C5—C6	1.392 (2)	C12—N1	1.136 (2)
C5—H5	0.9300	N2—O3	1.2169 (17)
C6—C7	1.3949 (19)	N2—O4	1.2177 (17)
C6—N2	1.4547 (18)
C2—C1—C7	118.11 (13)	C1—C7—C8	118.17 (13)
C2—C1—H1	120.9	C9—C8—C7	125.06 (14)
C7—C1—H1	120.9	C9—C8—H8	117.5
O1—C2—C1	127.85 (13)	C7—C8—H8	117.5
O1—C2—C4	109.86 (13)	C8—C9—C12	121.93 (14)
C1—C2—C4	122.29 (13)	C8—C9—C10	120.68 (14)
O2—C3—O1	107.47 (12)	C12—C9—C10	117.36 (14)
O2—C3—H3A	110.2	O5—C10—O6	125.79 (15)
O1—C3—H3A	110.2	O5—C10—C9	123.73 (16)
O2—C3—H3B	110.2	O6—C10—C9	110.48 (15)
O1—C3—H3B	110.2	O6—C11—H11A	109.5
H3A—C3—H3B	108.5	O6—C11—H11B	109.5
O2—C4—C5	127.95 (13)	H11A—C11—H11B	109.5
O2—C4—C2	110.18 (13)	O6—C11—H11C	109.5
C5—C4—C2	121.88 (13)	H11A—C11—H11C	109.5
C4—C5—C6	116.13 (13)	H11B—C11—H11C	109.5
C4—C5—H5	121.9	N1—C12—C9	179.57 (18)
C6—C5—H5	121.9	O3—N2—O4	122.63 (13)
C5—C6—C7	123.46 (13)	O3—N2—C6	119.32 (13)
C5—C6—N2	115.83 (12)	O4—N2—C6	118.05 (13)
C7—C6—N2	120.64 (13)	C2—O1—C3	106.34 (11)
C6—C7—C1	118.12 (13)	C4—O2—C3	105.99 (12)
C6—C7—C8	123.67 (13)	C10—O6—C11	116.71 (16)
C7—C1—C2—O1	179.97 (15)	C7—C8—C9—C12	−6.3 (2)
C7—C1—C2—C4	−0.1 (2)	C7—C8—C9—C10	175.68 (13)
O1—C2—C4—O2	0.51 (18)	C8—C9—C10—O5	−0.7 (2)
C1—C2—C4—O2	−179.41 (14)	C12—C9—C10—O5	−178.88 (16)
O1—C2—C4—C5	−179.43 (13)	C8—C9—C10—O6	179.10 (13)
C1—C2—C4—C5	0.7 (2)	C12—C9—C10—O6	0.96 (19)
O2—C4—C5—C6	179.86 (14)	C5—C6—N2—O3	163.45 (14)
C2—C4—C5—C6	−0.2 (2)	C7—C6—N2—O3	−13.6 (2)
C4—C5—C6—C7	−0.7 (2)	C5—C6—N2—O4	−16.5 (2)
C4—C5—C6—N2	−177.74 (13)	C7—C6—N2—O4	166.40 (15)
C5—C6—C7—C1	1.2 (2)	C1—C2—O1—C3	−178.04 (16)
N2—C6—C7—C1	178.11 (13)	C4—C2—O1—C3	2.05 (18)
C5—C6—C7—C8	178.73 (13)	O2—C3—O1—C2	−3.74 (18)
N2—C6—C7—C8	−4.4 (2)	C5—C4—O2—C3	177.10 (16)
C2—C1—C7—C6	−0.8 (2)	C2—C4—O2—C3	−2.83 (17)
C2—C1—C7—C8	−178.41 (13)	O1—C3—O2—C4	4.01 (18)
C6—C7—C8—C9	135.22 (16)	O5—C10—O6—C11	−3.8 (2)
C1—C7—C8—C9	−47.3 (2)	C9—C10—O6—C11	176.34 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···O4i	0.97	2.51	3.247 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯O4i	0.97	2.51	3.247 (2)	132

Symmetry code: (i) .