(Z)-Ethyl 2-cyano-3-(1H-imidazol-2-yl)acrylate.

The crystal structure of the title compound, C9H9N3O2, features N-H⋯N and C-H⋯O inter-actions. The N-H⋯N inter-action generates a chain running along the a axis and the C-H⋯O inter-action generates a chain along the c axis. An intra-molecular C-H⋯O inter-action is also observed.

Related literature

For background references and the biological importance of related compounds, see: Bigi et al. (1999 ▶); Yu et al. (2000 ▶). For the synthesis, see: Knoevenagel (1898 ▶); Yadav et al. (2004 ▶).

Experimental

Crystal data

C9H9N3O2

M = 191.19

Orthorhombic,

a = 10.0768 (7) Å

b = 12.0387 (8) Å

c = 7.7047 (6) Å

V = 934.67 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.4 × 0.23 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.980, T max = 0.984

7118 measured reflections

1436 independent reflections

1189 reflections with ( > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.145

S = 0.83

1436 reflections

128 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813018278/fj2635sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018278/fj2635Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018278/fj2635Isup3.cml

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

C9H9N3O2	F(000) = 400
Mr = 191.19	Dx = 1.359 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	θ = 2.6–25.0°
a = 10.0768 (7) Å	µ = 0.10 mm−1
b = 12.0387 (8) Å	T = 293 K
c = 7.7047 (6) Å	Needle, pale yellow
V = 934.67 (12) Å3	0.4 × 0.23 × 0.2 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1436 independent reflections
Radiation source: fine-focus sealed tube	1189 reflections with ( > 2σ(I)
Graphite monochromator	Rint = 0.033
phi and ω scans	θmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −13→14
Tmin = 0.980, Tmax = 0.984	k = −16→12
7118 measured reflections	l = −10→10

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 0.83	w = 1/[σ2(Fo2) + (0.1215P)2 + 0.160P] where P = (Fo2 + 2Fc2)/3
1436 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.22 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
C1	0.1765 (3)	−0.1284 (2)	−0.3293 (4)	0.0457 (6)
H1	0.1447	−0.1956	−0.3719	0.055*
C2	0.3054 (2)	−0.0942 (2)	−0.3241 (4)	0.0447 (6)
H2	0.3770	−0.1355	−0.3647	0.054*
C3	0.1905 (2)	0.03689 (18)	−0.2134 (3)	0.0364 (5)
C4	0.1407 (2)	0.13759 (19)	−0.1392 (4)	0.0394 (5)
H4	0.0487	0.1416	−0.1308	0.047*
C5	0.20598 (19)	0.22724 (19)	−0.0798 (4)	0.0366 (4)
C6	0.1238 (2)	0.32086 (19)	−0.0127 (4)	0.0416 (5)
C7	0.1271 (3)	0.4938 (2)	0.1330 (5)	0.0623 (9)
H7A	0.0624	0.5220	0.0509	0.075*
H7B	0.0806	0.4701	0.2368	0.075*
C8	0.2242 (4)	0.5808 (3)	0.1760 (6)	0.0696 (10)
H8A	0.2917	0.5503	0.2499	0.104*
H8B	0.1802	0.6406	0.2350	0.104*
H8C	0.2641	0.6082	0.0713	0.104*
C9	0.3471 (2)	0.23680 (19)	−0.0740 (4)	0.0421 (5)
N1	0.10482 (18)	−0.04511 (16)	−0.2601 (3)	0.0420 (5)
H1A	0.0200	−0.0440	−0.2477	0.050*
N2	0.31525 (19)	0.00888 (17)	−0.2512 (3)	0.0396 (5)
N3	0.4589 (2)	0.2480 (2)	−0.0668 (5)	0.0642 (8)
O1	0.00530 (18)	0.32337 (16)	−0.0221 (4)	0.0626 (7)
O2	0.19908 (17)	0.40053 (15)	0.0574 (3)	0.0515 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0384 (11)	0.0307 (12)	0.0680 (15)	0.0007 (9)	−0.0019 (11)	−0.0053 (12)
C2	0.0371 (11)	0.0332 (12)	0.0637 (15)	0.0045 (9)	0.0035 (10)	−0.0040 (12)
C3	0.0309 (9)	0.0250 (10)	0.0533 (13)	−0.0030 (8)	0.0008 (8)	0.0027 (9)
C4	0.0323 (9)	0.0308 (11)	0.0551 (12)	−0.0001 (8)	0.0024 (10)	0.0029 (9)
C5	0.0348 (9)	0.0251 (9)	0.0500 (12)	0.0025 (7)	−0.0003 (9)	0.0015 (9)
C6	0.0371 (10)	0.0286 (11)	0.0591 (14)	−0.0003 (8)	0.0065 (10)	0.0011 (10)
C7	0.0554 (16)	0.0366 (14)	0.095 (2)	0.0014 (11)	0.0195 (16)	−0.0130 (15)
C8	0.086 (3)	0.0436 (15)	0.079 (2)	−0.0112 (15)	0.017 (2)	−0.0204 (16)
C9	0.0397 (11)	0.0264 (10)	0.0602 (14)	0.0028 (8)	−0.0018 (11)	−0.0017 (10)
N1	0.0291 (8)	0.0292 (9)	0.0677 (13)	−0.0027 (7)	0.0001 (9)	−0.0027 (10)
N2	0.0323 (9)	0.0297 (10)	0.0566 (11)	−0.0022 (7)	0.0014 (9)	0.0001 (8)
N3	0.0388 (10)	0.0502 (14)	0.103 (2)	0.0028 (9)	−0.0041 (14)	−0.0151 (15)
O1	0.0395 (9)	0.0418 (10)	0.1065 (19)	0.0051 (8)	0.0059 (10)	−0.0154 (11)
O2	0.0434 (9)	0.0291 (8)	0.0819 (15)	−0.0001 (6)	0.0067 (9)	−0.0126 (9)

C1—N1	1.346 (3)	C6—O1	1.197 (3)
C1—C2	1.363 (3)	C6—O2	1.337 (3)
C1—H1	0.9300	C7—C8	1.472 (5)
C2—N2	1.366 (3)	C7—O2	1.458 (3)
C2—H2	0.9300	C7—H7A	0.9700
C3—N2	1.334 (3)	C7—H7B	0.9700
C3—N1	1.360 (3)	C8—H8A	0.9600
C3—C4	1.431 (3)	C8—H8B	0.9600
C4—C5	1.344 (3)	C8—H8C	0.9600
C4—H4	0.9300	C9—N3	1.135 (3)
C5—C9	1.428 (3)	N1—H1A	0.8600
C5—C6	1.491 (3)
N1—C1—C2	105.9 (2)	C8—C7—O2	107.9 (3)
N1—C1—H1	127.0	C8—C7—H7A	110.1
C2—C1—H1	127.0	O2—C7—H7A	110.1
N2—C2—C1	110.8 (2)	C8—C7—H7B	110.1
N2—C2—H2	124.6	O2—C7—H7B	110.1
C1—C2—H2	124.6	H7A—C7—H7B	108.4
N2—C3—N1	110.9 (2)	C7—C8—H8A	109.5
N2—C3—C4	129.2 (2)	C7—C8—H8B	109.5
N1—C3—C4	119.9 (2)	H8A—C8—H8B	109.5
C5—C4—C3	130.1 (2)	C7—C8—H8C	109.5
C5—C4—H4	114.9	H8A—C8—H8C	109.5
C3—C4—H4	114.9	H8B—C8—H8C	109.5
C4—C5—C9	124.3 (2)	N3—C9—C5	177.6 (3)
C4—C5—C6	116.95 (19)	C1—N1—C3	107.74 (18)
C9—C5—C6	118.8 (2)	C1—N1—H1A	126.1
O1—C6—O2	124.9 (2)	C3—N1—H1A	126.1
O1—C6—C5	123.5 (2)	C3—N2—C2	104.54 (19)
O2—C6—C5	111.56 (19)	C6—O2—C7	115.6 (2)
N1—C1—C2—N2	0.6 (4)	C2—C1—N1—C3	−0.5 (3)
N2—C3—C4—C5	−4.1 (5)	N2—C3—N1—C1	0.2 (3)
N1—C3—C4—C5	177.9 (3)	C4—C3—N1—C1	178.6 (3)
C3—C4—C5—C9	−2.6 (5)	N1—C3—N2—C2	0.1 (3)
C3—C4—C5—C6	178.8 (3)	C4—C3—N2—C2	−178.1 (3)
C4—C5—C6—O1	−6.1 (5)	C1—C2—N2—C3	−0.4 (3)
C9—C5—C6—O1	175.1 (3)	O1—C6—O2—C7	2.7 (5)
C4—C5—C6—O2	174.2 (3)	C5—C6—O2—C7	−177.6 (3)
C9—C5—C6—O2	−4.5 (4)	C8—C7—O2—C6	−170.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.38	2.771 (3)	105
N1—H1A···N2i	0.86	2.11	2.951 (3)	167
C1—H1···O1ii	0.93	2.45	3.328 (4)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1	0.93	2.38	2.771 (3)	105
N1—H1A⋯N2i	0.86	2.11	2.951 (3)	167
C1—H1⋯O1ii	0.93	2.45	3.328 (4)	158

Symmetry codes: (i) ; (ii) .