(E)-Ethyl 2-cyano-3-(1H-pyrrol-2-yl)acrylate.

All the non-H atoms of the title compound, C(10)H(10)N(2)O(2), are nearly in the same plane with a maximum deviation of 0.093 (1) Å. In the crystal, adjacent mol-ecules are linked by pairs of inter-molecular N-H⋯O hydrogen bonds, generating inversion dimers with R(2) (2)(14) ring motifs.

Related literature

For background to and applications of pyrrole derivatives, see: Fischer & Orth (1934 ▶). For the Knoevenagel condensation reaction and its applications, see: Knoevenagel (1898 ▶); Bigi et al. (1999 ▶). For the synthesis of related compounds, see: Knizhnikov et al. (2007 ▶); Sarda et al. (2009 ▶). For related structures, see: Ye et al. (2009 ▶); Wang & Jian (2008 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C10H10N2O2

M = 190.20

Monoclinic,

a = 6.2811 (2) Å

b = 9.4698 (3) Å

c = 16.3936 (5) Å

β = 92.645 (3)°

V = 974.06 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.971, T max = 0.986

18157 measured reflections

1908 independent reflections

1574 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.06

1908 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811028790/is2752sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028790/is2752Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028790/is2752Isup3.cml

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

C10H10N2O2	F(000) = 400
Mr = 190.20	Dx = 1.297 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7544 reflections
a = 6.2811 (2) Å	θ = 3.5–29.0°
b = 9.4698 (3) Å	µ = 0.09 mm−1
c = 16.3936 (5) Å	T = 293 K
β = 92.645 (3)°	Rectangular, light yellow
V = 974.06 (5) Å3	0.30 × 0.20 × 0.15 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1908 independent reflections
Radiation source: fine-focus sealed tube	1574 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
Tmin = 0.971, Tmax = 0.986	l = −20→20
18157 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.1138P] where P = (Fo2 + 2Fc2)/3
1908 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.19 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	−0.1517 (2)	0.73171 (17)	0.56284 (9)	0.0557 (4)
H1	−0.2260	0.7170	0.6099	0.067*
C2	−0.2045 (3)	0.82705 (18)	0.50230 (9)	0.0596 (4)
H2	−0.3208	0.8879	0.5007	0.072*
C3	−0.0526 (2)	0.81600 (16)	0.44393 (9)	0.0522 (4)
H3	−0.0488	0.8687	0.3962	0.063*
C4	0.0926 (2)	0.71274 (13)	0.46903 (7)	0.0403 (3)
C5	0.2764 (2)	0.65298 (13)	0.43588 (8)	0.0403 (3)
H5	0.3441	0.5838	0.4679	0.048*
C6	0.36856 (19)	0.68137 (13)	0.36460 (7)	0.0390 (3)
C7	0.2877 (2)	0.78645 (15)	0.30869 (8)	0.0433 (3)
C8	0.5592 (2)	0.60070 (14)	0.34340 (7)	0.0400 (3)
C9	0.8147 (2)	0.56123 (16)	0.24473 (8)	0.0502 (4)
H9A	0.7809	0.4614	0.2415	0.060*
H9B	0.9363	0.5737	0.2827	0.060*
C10	0.8645 (3)	0.61655 (18)	0.16209 (9)	0.0593 (4)
H10A	0.7448	0.6008	0.1247	0.089*
H10B	0.9870	0.5683	0.1429	0.089*
H10C	0.8937	0.7159	0.1657	0.089*
N1	0.02503 (19)	0.66332 (12)	0.54287 (7)	0.0472 (3)
H1A	0.0873	0.5982	0.5717	0.057*
N2	0.2208 (2)	0.87126 (15)	0.26485 (8)	0.0631 (4)
O1	0.63859 (15)	0.50906 (11)	0.38609 (6)	0.0539 (3)
O2	0.63298 (14)	0.64028 (10)	0.27206 (5)	0.0454 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0510 (8)	0.0684 (10)	0.0490 (8)	0.0055 (7)	0.0159 (6)	−0.0045 (7)
C2	0.0537 (9)	0.0672 (10)	0.0587 (9)	0.0183 (7)	0.0105 (7)	0.0000 (8)
C3	0.0544 (8)	0.0562 (9)	0.0464 (8)	0.0119 (7)	0.0072 (6)	0.0048 (6)
C4	0.0420 (7)	0.0431 (7)	0.0359 (6)	−0.0008 (6)	0.0034 (5)	−0.0025 (5)
C5	0.0402 (7)	0.0420 (7)	0.0386 (7)	0.0013 (5)	0.0018 (5)	−0.0001 (5)
C6	0.0375 (7)	0.0422 (7)	0.0375 (6)	−0.0014 (5)	0.0024 (5)	0.0005 (5)
C7	0.0414 (7)	0.0477 (8)	0.0412 (7)	0.0014 (6)	0.0068 (5)	0.0012 (6)
C8	0.0388 (7)	0.0434 (7)	0.0380 (7)	−0.0012 (5)	0.0032 (5)	0.0002 (5)
C9	0.0450 (7)	0.0541 (8)	0.0526 (8)	0.0072 (6)	0.0133 (6)	0.0026 (7)
C10	0.0608 (9)	0.0625 (10)	0.0565 (9)	0.0038 (7)	0.0227 (7)	0.0043 (7)
N1	0.0487 (7)	0.0524 (7)	0.0412 (6)	0.0062 (5)	0.0091 (5)	0.0043 (5)
N2	0.0660 (9)	0.0669 (8)	0.0570 (8)	0.0129 (7)	0.0092 (6)	0.0184 (7)
O1	0.0540 (6)	0.0611 (6)	0.0474 (6)	0.0163 (5)	0.0092 (4)	0.0123 (5)
O2	0.0425 (5)	0.0507 (6)	0.0437 (5)	0.0047 (4)	0.0120 (4)	0.0066 (4)

C1—N1	1.3386 (18)	C6—C8	1.4753 (18)
C1—C2	1.371 (2)	C7—N2	1.1447 (17)
C1—H1	0.9300	C8—O1	1.2080 (15)
C2—C3	1.386 (2)	C8—O2	1.3316 (15)
C2—H2	0.9300	C9—O2	1.4528 (16)
C3—C4	1.3869 (19)	C9—C10	1.4991 (19)
C3—H3	0.9300	C9—H9A	0.9700
C4—N1	1.3827 (16)	C9—H9B	0.9700
C4—C5	1.4165 (18)	C10—H10A	0.9600
C5—C6	1.3546 (18)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C6—C7	1.4301 (18)	N1—H1A	0.8600
N1—C1—C2	108.49 (12)	O1—C8—O2	124.05 (12)
N1—C1—H1	125.8	O1—C8—C6	123.60 (11)
C2—C1—H1	125.8	O2—C8—C6	112.35 (11)
C1—C2—C3	107.40 (13)	O2—C9—C10	107.37 (12)
C1—C2—H2	126.3	O2—C9—H9A	110.2
C3—C2—H2	126.3	C10—C9—H9A	110.2
C2—C3—C4	108.22 (13)	O2—C9—H9B	110.2
C2—C3—H3	125.9	C10—C9—H9B	110.2
C4—C3—H3	125.9	H9A—C9—H9B	108.5
N1—C4—C3	105.90 (12)	C9—C10—H10A	109.5
N1—C4—C5	119.30 (12)	C9—C10—H10B	109.5
C3—C4—C5	134.80 (12)	H10A—C10—H10B	109.5
C6—C5—C4	129.78 (12)	C9—C10—H10C	109.5
C6—C5—H5	115.1	H10A—C10—H10C	109.5
C4—C5—H5	115.1	H10B—C10—H10C	109.5
C5—C6—C7	122.53 (12)	C1—N1—C4	110.00 (12)
C5—C6—C8	118.95 (11)	C1—N1—H1A	125.0
C7—C6—C8	118.53 (11)	C4—N1—H1A	125.0
N2—C7—C6	178.93 (14)	C8—O2—C9	115.85 (10)
N1—C1—C2—C3	−0.38 (18)	C7—C6—C8—O1	−179.34 (12)
C1—C2—C3—C4	0.31 (18)	C5—C6—C8—O2	−179.66 (11)
C2—C3—C4—N1	−0.12 (16)	C7—C6—C8—O2	0.57 (17)
C2—C3—C4—C5	178.72 (15)	C2—C1—N1—C4	0.31 (18)
N1—C4—C5—C6	178.23 (12)	C3—C4—N1—C1	−0.11 (16)
C3—C4—C5—C6	−0.5 (3)	C5—C4—N1—C1	−179.17 (12)
C4—C5—C6—C7	1.1 (2)	O1—C8—O2—C9	2.78 (19)
C4—C5—C6—C8	−178.64 (12)	C6—C8—O2—C9	−177.13 (10)
C5—C6—C8—O1	0.4 (2)	C10—C9—O2—C8	176.96 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.09	2.874 (2)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.09	2.874 (2)	151

Symmetry code: (i) .