Methyl (2E)-2-cyano-3-(dimethyl-amino)-prop-2-enoate.

In the title compound, C(7)H(10)N(2)O(2), the dimethyl-amino group is twisted slightly relative to the acrylate fragment, forming a dihedral angle of 11.6 (1)°. In the crystal, molecules are linked via pairs of bifurcated C-H/H⋯O hydrogen bonds, forming inversion dimers, which are further connected by C-H⋯N hydrogen bonds into chains along the a-axis direction.

Related literature

For applications of enamines, see: Huang et al. (2007 ▶); Michael et al. (1999 ▶). For a related structure, see: Gupta et al. (2007 ▶).

Experimental

Crystal data

C7H10N2O2

M = 154.17

Triclinic,

a = 7.1102 (5) Å

b = 7.8170 (5) Å

c = 8.2454 (6) Å

α = 97.270 (6)°

β = 93.431 (6)°

γ = 115.680 (7)°

V = 406.31 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.830, T max = 1.000

6682 measured reflections

1593 independent reflections

1126 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.03

1593 reflections

103 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812042304/gk2525sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042304/gk2525Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042304/gk2525Isup3.cml

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

C7H10N2O2	Z = 2
Mr = 154.17	F(000) = 164
Triclinic, P1	Dx = 1.260 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1102 (5) Å	Cell parameters from 2720 reflections
b = 7.8170 (5) Å	θ = 3.5–29.0°
c = 8.2454 (6) Å	µ = 0.09 mm−1
α = 97.270 (6)°	T = 293 K
β = 93.431 (6)°	Block, white
γ = 115.680 (7)°	0.3 × 0.2 × 0.2 mm
V = 406.31 (5) Å3

Oxford Diffraction Xcalibur Sapphire3 diffractometer	1593 independent reflections
Radiation source: fine-focus sealed tube	1126 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.5°
ω scan	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −9→9
Tmin = 0.830, Tmax = 1.000	l = −10→10
6682 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) = 0.134	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0618P)2 + 0.0587P] where P = (Fo2 + 2Fc2)/3
1593 reflections	(Δ/σ)max = 0.001
103 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.13 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.0160 (2)	0.6248 (2)	0.82511 (17)	0.0648 (5)
O2	0.20619 (19)	0.77535 (19)	0.63425 (16)	0.0535 (4)
C1	0.1860 (3)	0.7109 (2)	0.7792 (2)	0.0438 (4)
C2	0.3885 (3)	0.7570 (2)	0.8695 (2)	0.0405 (4)
N1	0.5414 (2)	0.7293 (2)	1.13299 (19)	0.0475 (4)
N2	0.7150 (3)	0.9493 (3)	0.7343 (2)	0.0733 (6)
C3	0.3876 (3)	0.7106 (2)	1.0252 (2)	0.0423 (4)
H3	0.2552	0.6567	1.0599	0.051*
C4	0.5009 (3)	0.6883 (3)	1.2987 (3)	0.0666 (6)
H4A	0.3525	0.6365	1.3051	0.100*
H4B	0.5737	0.8051	1.3773	0.100*
H4C	0.5498	0.5964	1.3228	0.100*
C5	0.7594 (3)	0.7984 (3)	1.1018 (3)	0.0616 (6)
H5A	0.7642	0.7414	0.9929	0.092*
H5B	0.8346	0.7633	1.1813	0.092*
H5C	0.8230	0.9360	1.1107	0.092*
C6	0.5718 (3)	0.8620 (3)	0.7958 (2)	0.0478 (5)
C7	0.0158 (3)	0.7445 (3)	0.5374 (3)	0.0611 (6)
H7A	−0.0765	0.6090	0.5118	0.092*
H7B	0.0491	0.7950	0.4371	0.092*
H7C	−0.0524	0.8090	0.5988	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.0394 (8)	0.0845 (10)	0.0603 (9)	0.0136 (7)	0.0073 (7)	0.0287 (8)
O2	0.0476 (8)	0.0646 (9)	0.0472 (8)	0.0215 (6)	0.0059 (6)	0.0186 (6)
C1	0.0443 (11)	0.0417 (9)	0.0417 (10)	0.0157 (8)	0.0064 (8)	0.0071 (7)
C2	0.0356 (9)	0.0396 (9)	0.0435 (10)	0.0140 (7)	0.0079 (8)	0.0061 (7)
N1	0.0395 (8)	0.0516 (9)	0.0457 (9)	0.0151 (7)	0.0027 (7)	0.0095 (7)
N2	0.0502 (11)	0.0953 (15)	0.0766 (13)	0.0263 (10)	0.0241 (10)	0.0380 (11)
C3	0.0369 (10)	0.0385 (9)	0.0467 (10)	0.0122 (8)	0.0069 (8)	0.0073 (7)
C4	0.0583 (13)	0.0804 (15)	0.0516 (12)	0.0205 (11)	0.0027 (10)	0.0200 (11)
C5	0.0422 (11)	0.0738 (14)	0.0650 (14)	0.0223 (10)	0.0028 (10)	0.0140 (11)
C6	0.0430 (10)	0.0534 (11)	0.0475 (11)	0.0210 (9)	0.0086 (9)	0.0114 (9)
C7	0.0567 (13)	0.0726 (14)	0.0569 (13)	0.0298 (11)	0.0024 (10)	0.0200 (11)

O1—C1	1.213 (2)	C3—H3	0.9300
O2—C1	1.346 (2)	C4—H4A	0.9600
O2—C7	1.438 (2)	C4—H4B	0.9600
C1—C2	1.454 (2)	C4—H4C	0.9600
C2—C3	1.377 (2)	C5—H5A	0.9600
C2—C6	1.427 (2)	C5—H5B	0.9600
N1—C3	1.311 (2)	C5—H5C	0.9600
N1—C5	1.455 (2)	C7—H7A	0.9600
N1—C4	1.460 (2)	C7—H7B	0.9600
N2—C6	1.143 (2)	C7—H7C	0.9600
C1—O2—C7	116.82 (15)	N1—C4—H4C	109.5
O1—C1—O2	122.40 (17)	H4A—C4—H4C	109.5
O1—C1—C2	125.53 (17)	H4B—C4—H4C	109.5
O2—C1—C2	112.07 (15)	N1—C5—H5A	109.5
C3—C2—C6	125.51 (17)	N1—C5—H5B	109.5
C3—C2—C1	117.00 (15)	H5A—C5—H5B	109.5
C6—C2—C1	117.21 (16)	N1—C5—H5C	109.5
C3—N1—C5	124.10 (16)	H5A—C5—H5C	109.5
C3—N1—C4	120.07 (15)	H5B—C5—H5C	109.5
C5—N1—C4	115.77 (16)	N2—C6—C2	177.6 (2)
N1—C3—C2	131.07 (16)	O2—C7—H7A	109.5
N1—C3—H3	114.5	O2—C7—H7B	109.5
C2—C3—H3	114.5	H7A—C7—H7B	109.5
N1—C4—H4A	109.5	O2—C7—H7C	109.5
N1—C4—H4B	109.5	H7A—C7—H7C	109.5
H4A—C4—H4B	109.5	H7B—C7—H7C	109.5
C7—O2—C1—O1	2.5 (3)	O2—C1—C2—C6	0.9 (2)
C7—O2—C1—C2	−177.56 (15)	C5—N1—C3—C2	−4.1 (3)
O1—C1—C2—C3	−4.8 (3)	C4—N1—C3—C2	173.00 (19)
O2—C1—C2—C3	175.27 (15)	C6—C2—C3—N1	−8.1 (3)
O1—C1—C2—C6	−179.14 (17)	C1—C2—C3—N1	178.06 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.56	3.370 (2)	146
C4—H4A···O1i	0.96	2.58	3.415 (3)	145
C7—H7C···N2ii	0.96	2.58	3.535 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.56	3.370 (2)	146
C4—H4A⋯O1i	0.96	2.58	3.415 (3)	145
C7—H7C⋯N2ii	0.96	2.58	3.535 (3)	172

Symmetry codes: (i) ; (ii) .