2-Cyano-N,N-dimethyl­acetamide

Liu, S.; Zhu, H.-J.; Yu, G.-Q.; Du, G.; Lv, L.-Z.

doi:10.1107/S1600536812000748

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o457

doi:10.1107/S1600536812000748

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2-Cyano-N,N-dimethylacetamide

Shan Liu,^a ^* Hong-Jun Zhu,^b Guo-Quan Yu,^c Gang Du ^c and Liang-Zhong Lv ^c

^aNanjing College of Chemical Technology, No. 625, Geguan Road, Luhe, Nanjing 210048, People's Republic of China, ^bDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^cJiangsu Changqing Agrochemical Co. Ltd, No.1 Jiangling Road, Putou Town, Jiangdu City, Jiangsu 225218, People's Republic of China
^*Correspondence e-mail: dols80@163.com

(Received 26 December 2011; accepted 8 January 2012; online 18 January 2012)

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, P 2₁ /c
a = 4.1690 (8) Å
b = 9.3940 (19) Å
c = 15.880 (3) Å
β = 92.67 (3)°
V = 621.2 (2) Å³
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[F² > 2σ(F²)] = 0.068
wR(F²) = 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

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) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global, n1. DOI: 10.1107/S1600536812000748/lx2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000748/lx2222Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000748/lx2222Isup3.cml

checkCIF report

Comment top

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).

Related literature top

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 top

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.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); 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 (Sheldrick, 2008).

Figures top

	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.]

2-Cyano-N,N-dimethylacetamide top

Crystal data top

C₅H₈N₂O	F(000) = 240
M_r = 112.13	D_x = 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 top

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

Refinement top

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(F_o²) + (0.09P)² + 0.P] where P = (F_o² + 2F_c²)/3
1129 reflections	(Δ/σ)_max < 0.001
73 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₅H₈N₂O	V = 621.2 (2) Å³
M_r = 112.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.1690 (8) Å	µ = 0.09 mm⁻¹
b = 9.3940 (19) Å	T = 298 K
c = 15.880 (3) Å	0.30 × 0.20 × 0.10 mm
β = 92.67 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	666 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.051
T_min = 0.975, T_max = 0.991	3 standard reflections every 200 reflections
1294 measured reflections	intensity decay: 1%
1129 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
1129 reflections	Δρ_min = −0.18 e Å⁻³
73 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₅H₈N₂O
M_r	112.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	4.1690 (8), 9.3940 (19), 15.880 (3)
β (°)	92.67 (3)
V (Å³)	621.2 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.975, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	1294, 1129, 666
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.167, 1.01
No. of reflections	1129
No. of parameters	73
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Oⁱ	0.9700	2.3800	3.300 (3)	159.00
C4—H4B···Oⁱⁱ	0.9700	2.4100	3.141 (3)	132.00

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar