2-Cyano-N,N-dimethyl­acetamide

Abstract

In the crystal structure of the title compound, C₅H₈N₂O, mol­ecules are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For uses of 2-cyano-N, N-dimethyl­acetamide, see: Liu et al. (2011 ▶). For the synthesis, see: Liu et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

• C₅H₈N₂O

• M _r = 112.13

• Monoclinic,

• a = 4.1690 (8) Å

• b = 9.3940 (19) Å

• c = 15.880 (3) Å

• β = 92.67 (3)°

• V = 621.2 (2) ų

• Z = 4

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 298 K

• 0.30 × 0.20 × 0.10 mm

Data collection

• Enraf–Nonius CAD-4 diffractometer

• Absorption correction: ψ scan (North et al., 1968) ▶ T _min = 0.975, T _max = 0.991

• 1294 measured reflections

• 1129 independent reflections

• 666 reflections with I > 2σ(I)

• R _int = 0.051

• 3 standard reflections every 200 reflections intensity decay: 1%

Refinement

• R[F ² > 2σ(F ²)] = 0.068

• wR(F ²) = 0.167

• S = 1.01

• 1129 reflections

• 73 parameters

• H-atom parameters constrained

• Δρ_max = 0.22 e Å⁻³

• Δρ_min = −0.18 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1985) ▶; cell refinement: CAD-4 Software ▶; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812000748/lx2222Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯Oi	0.97	2.38	3.300 (3)	159
C4—H4B⋯Oii	0.97	2.41	3.141 (3)	132

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Comment

2-Cyano-N, N-dimethylacetamide is an important intermediate used to synthesize the herbicide of nicosulfuron (Liu et al., 2011). We report here the crystal structure of the title compound (Fig. 1).

In the title molecule, bond lengths (Allen et al. , 1987) and angles are within normal ranges. In the crystal packing (Fig. 2), molecules are linked by weak intermolecular C–H···O hydrogen bonds (see, Table 1).

Experimental

2-Cyano-N,N-dimethylacetamide was prepared by the method reported in literature (Liu et al., 2011). Single crystals were obtained by dissolving 2-Cyano-N, N-dimethylacetamide (0.50 g, 4.46 mmol) in ethyl acetate (30 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Refinement

H atoms were positioned geometrically, with O–H = 0.82 and C–H = 0.93Å for aromatic H, and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C/O), where x = 1.2 for aromatic H and x = 1.5 for other H.

Figures

Fig. 1.

The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 40% probability level. H atoms are presented as small spheres of arbitrary radius.

Fig. 2.

A view of the C–H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmter codes: (i) - x + 1, y + 1/2 , - z + 1/2; (ii) - x, y + 1/2, - z + 1/2; (iii) - x + 1, y - 1/2, - z + 1/2; (iv) - x , y -1/2, - z -1/2.]

Crystal data

C5H8N2O	F(000) = 240
Mr = 112.13	Dx = 1.199 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 4.1690 (8) Å	θ = 9–13°
b = 9.3940 (19) Å	µ = 0.09 mm−1
c = 15.880 (3) Å	T = 298 K
β = 92.67 (3)°	Block, brown
V = 621.2 (2) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	666 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
graphite	θmax = 25.4°, θmin = 2.5°
ω/2θ scans	h = 0→5
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.975, Tmax = 0.991	l = −19→19
1294 measured reflections	3 standard reflections every 200 reflections
1129 independent reflections	intensity decay: 1%

Refinement

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)] = 0.068	Hydrogen site location: difference Fourier map
wR(F2) = 0.167	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.09P)2 + 0.P] where P = (Fo2 + 2Fc2)/3
1129 reflections	(Δ/σ)max < 0.001
73 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O	0.2785 (4)	0.08459 (15)	0.22552 (10)	0.0789 (6)
C4	0.1898 (6)	0.3244 (2)	0.26152 (15)	0.0703 (7)
H4A	0.3718	0.3851	0.2766	0.084*
H4B	0.0286	0.3824	0.2319	0.084*
C3	0.2962 (6)	0.2083 (2)	0.20353 (15)	0.0617 (6)
N1	0.4071 (5)	0.2461 (2)	0.13046 (13)	0.0747 (7)
C5	0.0598 (7)	0.2697 (3)	0.33702 (18)	0.0758 (8)
C2	0.5089 (8)	0.1366 (3)	0.07292 (18)	0.0956 (9)
H2A	0.4964	0.0451	0.0995	0.143*
H2B	0.7263	0.1545	0.0585	0.143*
H2C	0.3715	0.1378	0.0227	0.143*
N2	−0.0412 (8)	0.2295 (3)	0.39639 (19)	0.1157 (10)
C1	0.4201 (9)	0.3936 (3)	0.09947 (19)	0.1010 (11)
H1A	0.3514	0.4574	0.1423	0.151*
H1B	0.2812	0.4033	0.0499	0.151*
H1C	0.6363	0.4163	0.0860	0.151*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O	0.1110 (14)	0.0480 (10)	0.0791 (12)	−0.0014 (10)	0.0192 (10)	0.0048 (8)
C4	0.0821 (16)	0.0537 (14)	0.0757 (17)	0.0009 (13)	0.0097 (13)	−0.0052 (11)
C3	0.0797 (16)	0.0448 (12)	0.0604 (14)	−0.0005 (12)	0.0003 (11)	0.0023 (10)
N1	0.1086 (18)	0.0552 (11)	0.0609 (12)	−0.0038 (12)	0.0102 (11)	0.0037 (9)
C5	0.0924 (18)	0.0651 (15)	0.0708 (18)	−0.0047 (15)	0.0125 (14)	−0.0105 (13)
C2	0.128 (2)	0.093 (2)	0.0672 (17)	0.0092 (19)	0.0192 (16)	−0.0067 (15)
N2	0.141 (2)	0.116 (2)	0.094 (2)	−0.0157 (19)	0.0406 (18)	−0.0064 (17)
C1	0.157 (3)	0.0709 (17)	0.0753 (19)	−0.015 (2)	0.0080 (18)	0.0182 (14)

Geometric parameters (Å, °)

O—C3	1.217 (2)	C5—N2	1.116 (3)
C4—C5	1.434 (4)	C2—H2A	0.9600
C4—C3	1.507 (3)	C2—H2B	0.9600
C4—H4A	0.9700	C2—H2C	0.9600
C4—H4B	0.9700	C1—H1A	0.9600
C3—N1	1.318 (3)	C1—H1B	0.9600
N1—C2	1.453 (3)	C1—H1C	0.9600
N1—C1	1.472 (3)
C5—C4—C3	112.6 (2)	N1—C2—H2A	109.5
C5—C4—H4A	109.1	N1—C2—H2B	109.5
C3—C4—H4A	109.1	H2A—C2—H2B	109.5
C5—C4—H4B	109.1	N1—C2—H2C	109.5
C3—C4—H4B	109.1	H2A—C2—H2C	109.5
H4A—C4—H4B	107.8	H2B—C2—H2C	109.5
O—C3—N1	122.6 (2)	N1—C1—H1A	109.5
O—C3—C4	119.5 (2)	N1—C1—H1B	109.5
N1—C3—C4	117.94 (19)	H1A—C1—H1B	109.5
C3—N1—C2	119.2 (2)	N1—C1—H1C	109.5
C3—N1—C1	124.6 (2)	H1A—C1—H1C	109.5
C2—N1—C1	116.1 (2)	H1B—C1—H1C	109.5
N2—C5—C4	178.7 (3)
C5—C4—C3—O	−3.2 (3)	O—C3—N1—C1	177.2 (3)
C5—C4—C3—N1	177.1 (2)	C4—C3—N1—C1	−3.1 (4)
O—C3—N1—C2	0.8 (4)	C3—C4—C5—N2	167 (15)
C4—C3—N1—C2	−179.5 (2)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Oi	0.97	2.38	3.300 (3)	159.
C4—H4B···Oii	0.97	2.41	3.141 (3)	132.

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x, y+1/2, −z+1/2.