(E)-Ethyl 2-cyano-3-(3,4-dihydr-oxy-5-nitro-phen-yl)acrylate.

The title compound, C(12)H(10)N(2)O(6), was synthesized via a Knoevenagel condensation and crystallized from ethanol. In the crystal, strong classical inter-molecular O-H⋯O hydrogen bonds and weak C-H⋯N contacts link the mol-ecules into ribbons extending along [010]. Intra-molecular O-H⋯O and C-H⋯N contacts support the planar conformation of the mol-ecules (mean deivation 0.0270 Å).

Related literature

For the syntheses of some potent and selective catechol O-methyl­transferase inhibitors, see: Bäckström et al. (1989 ▶). For structure–activity relationships of catechol O-methyl­transferase inhibitors, see: Tervo et al. (2003 ▶). For Entacapone-related crystal structures, see: Zheng et al. (2007 ▶). For the synthesis and anti­cancer evaluation of E-2-cyano-(3-substituted phen­yl)acyl­amides, see: Zhou et al. (2009 ▶).

Experimental

Crystal data

C12H10N2O6

M = 278.22

Monoclinic,

a = 24.983 (9) Å

b = 13.485 (5) Å

c = 7.312 (3) Å

β = 105.911 (4)°

V = 2369.0 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 93 K

0.40 × 0.20 × 0.10 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

Absorption correction: none

9288 measured reflections

2714 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.118

S = 1.00

2714 reflections

190 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035132/si2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035132/si2196Isup2.hkl

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

C12H10N2O6	F(000) = 1152
Mr = 278.22	Dx = 1.560 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3450 reflections
a = 24.983 (9) Å	θ = 3.0–27.5°
b = 13.485 (5) Å	µ = 0.13 mm−1
c = 7.312 (3) Å	T = 93 K
β = 105.911 (4)°	Prism, yellow
V = 2369.0 (16) Å3	0.40 × 0.20 × 0.10 mm
Z = 8

Rigaku AFC10/Saturn724+ diffractometer	2134 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.042
graphite	θmax = 27.6°, θmin = 3.0°
Detector resolution: 28.5714 pixels mm-1	h = −28→32
multi–scan	k = −17→17
9288 measured reflections	l = −9→6
2714 independent 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0596P)2 + 0.69P] where P = (Fo2 + 2Fc2)/3
2714 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
O1	0.39296 (5)	0.60992 (8)	0.12800 (18)	0.0219 (3)
O2	0.45623 (5)	0.47578 (9)	0.04941 (17)	0.0222 (3)
O3	0.47644 (5)	0.28865 (9)	0.03118 (18)	0.0269 (3)
O4	0.41766 (5)	0.17833 (9)	0.07290 (19)	0.0292 (3)
O5	0.13633 (5)	0.39925 (8)	0.35194 (16)	0.0196 (3)
O6	0.17659 (5)	0.25177 (9)	0.32497 (17)	0.0251 (3)
N1	0.20946 (6)	0.59192 (11)	0.2676 (2)	0.0237 (3)
N2	0.43188 (6)	0.26508 (11)	0.0670 (2)	0.0222 (3)
C1	0.32709 (7)	0.48910 (12)	0.1768 (2)	0.0179 (4)
H1	0.3033	0.5391	0.2023	0.022*
C2	0.37531 (7)	0.51576 (12)	0.1344 (2)	0.0174 (4)
C3	0.41109 (7)	0.44238 (13)	0.0937 (2)	0.0180 (4)
C4	0.39609 (7)	0.34321 (12)	0.1026 (2)	0.0178 (4)
C5	0.34721 (7)	0.31586 (12)	0.1455 (2)	0.0189 (4)
H5	0.3379	0.2477	0.1489	0.023*
C6	0.31215 (7)	0.38778 (12)	0.1831 (2)	0.0177 (4)
C7	0.26290 (7)	0.35205 (12)	0.2309 (2)	0.0186 (4)
H7	0.2601	0.2819	0.2352	0.022*
C8	0.22018 (7)	0.40137 (12)	0.2704 (2)	0.0182 (4)
C9	0.17571 (7)	0.34244 (12)	0.3181 (2)	0.0188 (4)
C10	0.21410 (7)	0.50688 (13)	0.2690 (2)	0.0189 (4)
C11	0.09158 (7)	0.34963 (13)	0.4102 (2)	0.0216 (4)
H11A	0.1072	0.3013	0.5129	0.026*
H11B	0.0668	0.3138	0.3013	0.026*
C12	0.05971 (7)	0.42919 (13)	0.4796 (3)	0.0248 (4)
H12A	0.0840	0.4609	0.5927	0.030*
H12B	0.0276	0.3995	0.5119	0.030*
H12C	0.0467	0.4789	0.3795	0.030*
H2O	0.4735 (10)	0.4161 (19)	0.024 (3)	0.055 (7)*
H1O	0.3692 (11)	0.659 (2)	0.139 (3)	0.063 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0197 (6)	0.0149 (6)	0.0348 (7)	−0.0012 (5)	0.0136 (5)	0.0001 (5)
O2	0.0176 (6)	0.0218 (7)	0.0314 (7)	−0.0007 (5)	0.0138 (5)	0.0004 (5)
O3	0.0211 (7)	0.0268 (7)	0.0379 (7)	0.0035 (5)	0.0169 (6)	0.0005 (6)
O4	0.0312 (7)	0.0163 (6)	0.0449 (8)	0.0022 (5)	0.0184 (6)	−0.0011 (5)
O5	0.0177 (6)	0.0184 (6)	0.0259 (6)	−0.0003 (5)	0.0115 (5)	0.0015 (5)
O6	0.0243 (7)	0.0172 (6)	0.0395 (8)	−0.0008 (5)	0.0183 (6)	0.0000 (5)
N1	0.0206 (8)	0.0207 (8)	0.0323 (8)	0.0006 (6)	0.0117 (6)	0.0001 (6)
N2	0.0214 (8)	0.0199 (7)	0.0268 (8)	0.0047 (6)	0.0094 (6)	−0.0005 (6)
C1	0.0162 (8)	0.0175 (8)	0.0215 (8)	0.0014 (6)	0.0076 (7)	−0.0003 (6)
C2	0.0180 (9)	0.0144 (8)	0.0206 (8)	0.0010 (6)	0.0067 (7)	0.0008 (6)
C3	0.0154 (8)	0.0203 (8)	0.0195 (8)	0.0004 (6)	0.0068 (7)	0.0000 (6)
C4	0.0173 (8)	0.0164 (8)	0.0208 (8)	0.0039 (6)	0.0069 (7)	−0.0003 (6)
C5	0.0192 (8)	0.0176 (8)	0.0211 (8)	−0.0004 (7)	0.0074 (7)	−0.0004 (6)
C6	0.0169 (8)	0.0176 (8)	0.0198 (8)	−0.0014 (6)	0.0070 (7)	−0.0004 (6)
C7	0.0204 (9)	0.0157 (8)	0.0211 (8)	−0.0019 (6)	0.0081 (7)	0.0003 (6)
C8	0.0188 (8)	0.0170 (8)	0.0202 (8)	−0.0005 (6)	0.0076 (7)	−0.0003 (6)
C9	0.0183 (9)	0.0193 (8)	0.0206 (8)	−0.0007 (7)	0.0085 (7)	−0.0013 (7)
C10	0.0146 (8)	0.0216 (9)	0.0223 (8)	−0.0013 (7)	0.0082 (7)	−0.0005 (7)
C11	0.0194 (9)	0.0221 (9)	0.0274 (9)	−0.0044 (7)	0.0133 (7)	−0.0010 (7)
C12	0.0224 (10)	0.0227 (9)	0.0346 (10)	−0.0005 (7)	0.0167 (8)	−0.0016 (7)

O1—C2	1.3491 (19)	C3—C4	1.395 (2)
O1—H1O	0.90 (3)	C4—C5	1.391 (2)
O2—C3	1.334 (2)	C5—C6	1.384 (2)
O2—H2O	0.95 (3)	C5—H5	0.9500
O3—N2	1.2528 (19)	C6—C7	1.450 (2)
O4—N2	1.2266 (19)	C7—C8	1.354 (2)
O5—C9	1.322 (2)	C7—H7	0.9500
O5—C11	1.463 (2)	C8—C10	1.431 (2)
O6—C9	1.224 (2)	C8—C9	1.484 (2)
N1—C10	1.152 (2)	C11—C12	1.505 (2)
N2—C4	1.451 (2)	C11—H11A	0.9900
C1—C2	1.372 (2)	C11—H11B	0.9900
C1—C6	1.420 (2)	C12—H12A	0.9800
C1—H1	0.9500	C12—H12B	0.9800
C2—C3	1.419 (2)	C12—H12C	0.9800
C2—O1—H1O	117.0 (17)	C1—C6—C7	125.12 (15)
C3—O2—H2O	102.7 (15)	C8—C7—C6	131.17 (16)
C9—O5—C11	117.16 (13)	C8—C7—H7	114.4
O4—N2—O3	122.12 (14)	C6—C7—H7	114.4
O4—N2—C4	119.20 (15)	C7—C8—C10	125.13 (15)
O3—N2—C4	118.68 (14)	C7—C8—C9	118.16 (16)
C2—C1—C6	120.95 (15)	C10—C8—C9	116.71 (15)
C2—C1—H1	119.5	O6—C9—O5	125.26 (15)
C6—C1—H1	119.5	O6—C9—C8	122.58 (15)
O1—C2—C1	124.76 (15)	O5—C9—C8	112.16 (15)
O1—C2—C3	114.74 (15)	N1—C10—C8	179.64 (18)
C1—C2—C3	120.49 (15)	O5—C11—C12	106.83 (14)
O2—C3—C4	126.20 (15)	O5—C11—H11A	110.4
O2—C3—C2	116.01 (15)	C12—C11—H11A	110.4
C4—C3—C2	117.79 (15)	O5—C11—H11B	110.4
C5—C4—C3	121.88 (15)	C12—C11—H11B	110.4
C5—C4—N2	118.04 (15)	H11A—C11—H11B	108.6
C3—C4—N2	120.08 (15)	C11—C12—H12A	109.5
C6—C5—C4	120.10 (15)	C11—C12—H12B	109.5
C6—C5—H5	119.9	H12A—C12—H12B	109.5
C4—C5—H5	119.9	C11—C12—H12C	109.5
C5—C6—C1	118.76 (15)	H12A—C12—H12C	109.5
C5—C6—C7	116.10 (15)	H12B—C12—H12C	109.5
C6—C1—C2—O1	−179.03 (15)	C4—C5—C6—C1	0.1 (2)
C6—C1—C2—C3	0.7 (2)	C4—C5—C6—C7	−178.53 (15)
O1—C2—C3—O2	−1.9 (2)	C2—C1—C6—C5	0.0 (2)
C1—C2—C3—O2	178.35 (14)	C2—C1—C6—C7	178.44 (15)
O1—C2—C3—C4	178.37 (14)	C5—C6—C7—C8	−178.25 (17)
C1—C2—C3—C4	−1.4 (2)	C1—C6—C7—C8	3.3 (3)
O2—C3—C4—C5	−178.26 (15)	C6—C7—C8—C10	1.4 (3)
C2—C3—C4—C5	1.4 (2)	C6—C7—C8—C9	−178.89 (16)
O2—C3—C4—N2	1.8 (3)	C11—O5—C9—O6	2.8 (2)
C2—C3—C4—N2	−178.46 (14)	C11—O5—C9—C8	−176.96 (13)
O4—N2—C4—C5	1.1 (2)	C7—C8—C9—O6	0.8 (3)
O3—N2—C4—C5	−178.91 (14)	C10—C8—C9—O6	−179.52 (16)
O4—N2—C4—C3	−179.01 (15)	C7—C8—C9—O5	−179.44 (14)
O3—N2—C4—C3	1.0 (2)	C10—C8—C9—O5	0.3 (2)
C3—C4—C5—C6	−0.8 (2)	C9—O5—C11—C12	168.12 (14)
N2—C4—C5—C6	179.10 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O6i	0.91 (3)	1.76 (3)	2.6692 (18)	176 (2)
C5—H5···N1ii	0.95	2.57	3.467 (3)	159
O2—H2O···O3	0.96 (3)	1.72 (3)	2.584 (2)	149 (2)
C1—H1···N1	0.95	2.62	3.474 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O6i	0.91 (3)	1.76 (3)	2.6692 (18)	176 (2)
C5—H5⋯N1ii	0.95	2.57	3.467 (3)	159
O2—H2O⋯O3	0.96 (3)	1.72 (3)	2.584 (2)	149 (2)
C1—H1⋯N1	0.95	2.62	3.474 (3)	150

Symmetry codes: (i) ; (ii) .