Crystal structure of 2-cyano-N-(furan-2-ylmeth-yl)acetamide.

In the title compound, C8H8N2O2, the acetamide unit is inclined to the furan ring by 76.7 (1)°. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds, generating C(4) chains along [100]. The carbonyl O atom is a bifurcated acceptor and an R (1) 2(6) ring is formed.

Related literature

For examples of biological properties of furan derivatives, see: Anupam et al. (2011 ▸). For the biological activities of some heterocyclic derivatives containing the acetamide moiety, see: Fallah-Tafti et al. (2011 ▸); Shams et al. (2011 ▸). For a related acetamide structure, see: Jasinski et al. (2013 ▸). For the crystal structure of similar compound, 2-cyano-N-furfuryl-3-(2-fur­yl)acryl­amide, see: Pomés Hernández et al. (1996 ▸).

Experimental

Crystal data

C8H8N2O2

M = 164.16

Monoclinic,

a = 4.8093 (4) Å

b = 14.9495 (16) Å

c = 11.4969 (11) Å

β = 93.482 (3)°

V = 825.06 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.946, T max = 0.986

7302 measured reflections

1455 independent reflections

1175 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.111

S = 1.09

1455 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL2014/7 and PLATON.

Crystal structure: contains datablock(s) I, globa. DOI: 10.1107/S2056989015010488/su5145sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015010488/su5145Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015010488/su5145Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015010488/su5145fig1.tif

The mol­ecular structure of the title compound, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015010488/su5145fig2.tif

A view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1404031

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H8N2O2	F(000) = 344
Mr = 164.16	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.8093 (4) Å	Cell parameters from 1455 reflections
b = 14.9495 (16) Å	θ = 2.2–25.0°
c = 11.4969 (11) Å	µ = 0.10 mm−1
β = 93.482 (3)°	T = 293 K
V = 825.06 (14) Å3	Block, colourless
Z = 4	0.3 × 0.2 × 0.2 mm

Bruker APEXII CCD diffractometer	1455 independent reflections
Radiation source: fine-focus sealed tube	1175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.0216 pixels mm-1	θmax = 25.0°, θmin = 2.2°
ω and φ scan	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −17→17
Tmin = 0.946, Tmax = 0.986	l = −12→13
7302 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0542P)2 + 0.1342P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1455 reflections	Δρmax = 0.14 e Å−3
109 parameters	Δρmin = −0.13 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.

	x	y	z	Uiso*/Ueq
C1	0.6009 (4)	0.71318 (14)	0.26789 (17)	0.0705 (5)
H1A	0.7123	0.7616	0.2502	0.085*
C2	0.6246 (4)	0.65991 (17)	0.37051 (16)	0.0816 (6)
H2	0.7549	0.6667	0.4330	0.098*
C3	0.4271 (5)	0.59926 (15)	0.36003 (17)	0.0777 (6)
H3	0.3942	0.5558	0.4154	0.093*
C4	0.3883 (3)	0.68024 (10)	0.20223 (13)	0.0483 (4)
C5	0.2563 (3)	0.70388 (11)	0.08709 (13)	0.0575 (4)
H5A	0.0559	0.7057	0.0925	0.069*
H5B	0.3170	0.7633	0.0660	0.069*
C6	0.1307 (3)	0.59915 (10)	−0.07049 (12)	0.0443 (4)
C7	0.2372 (3)	0.54182 (11)	−0.16707 (12)	0.0506 (4)
H7A	0.4373	0.5489	−0.1694	0.061*
H7B	0.1983	0.4793	−0.1522	0.061*
C8	0.1019 (4)	0.56845 (11)	−0.27806 (15)	0.0590 (4)
N1	0.3219 (2)	0.64139 (9)	−0.00467 (10)	0.0467 (3)
H1	0.4942	0.6316	−0.0164	0.056*
N2	−0.0079 (5)	0.59089 (12)	−0.36283 (16)	0.0947 (6)
O1	0.2779 (2)	0.60909 (8)	0.25698 (10)	0.0649 (4)
O2	−0.1197 (2)	0.60352 (9)	−0.05760 (11)	0.0713 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0617 (10)	0.0790 (13)	0.0714 (12)	−0.0144 (9)	0.0087 (9)	−0.0277 (10)
C2	0.0772 (13)	0.1118 (17)	0.0535 (11)	0.0191 (13)	−0.0147 (9)	−0.0260 (11)
C3	0.1019 (15)	0.0806 (14)	0.0500 (10)	0.0116 (12)	−0.0012 (10)	−0.0002 (9)
C4	0.0465 (8)	0.0503 (9)	0.0491 (8)	0.0010 (7)	0.0112 (6)	−0.0087 (7)
C5	0.0624 (10)	0.0576 (10)	0.0535 (9)	0.0132 (8)	0.0110 (7)	−0.0042 (7)
C6	0.0312 (7)	0.0565 (9)	0.0455 (8)	0.0070 (6)	0.0038 (6)	0.0080 (7)
C7	0.0404 (7)	0.0614 (10)	0.0497 (9)	0.0038 (7)	0.0004 (6)	−0.0016 (7)
C8	0.0713 (11)	0.0528 (10)	0.0526 (10)	−0.0083 (8)	0.0015 (8)	0.0013 (8)
N1	0.0339 (6)	0.0611 (8)	0.0458 (7)	0.0072 (5)	0.0079 (5)	−0.0030 (6)
N2	0.1407 (18)	0.0789 (12)	0.0611 (10)	−0.0056 (11)	−0.0226 (11)	0.0125 (9)
O1	0.0713 (8)	0.0667 (8)	0.0568 (7)	−0.0098 (6)	0.0037 (6)	0.0023 (6)
O2	0.0304 (6)	0.1024 (10)	0.0816 (9)	0.0076 (6)	0.0088 (5)	−0.0081 (7)

C1—C4	1.328 (2)	C5—H5A	0.9700
C1—C2	1.422 (3)	C5—H5B	0.9700
C1—H1A	0.9300	C6—O2	1.2238 (16)
C2—C3	1.314 (3)	C6—N1	1.3162 (18)
C2—H2	0.9300	C6—C7	1.516 (2)
C3—O1	1.355 (2)	C7—C8	1.452 (2)
C3—H3	0.9300	C7—H7A	0.9700
C4—O1	1.3602 (19)	C7—H7B	0.9700
C4—C5	1.476 (2)	C8—N2	1.131 (2)
C5—N1	1.4579 (19)	N1—H1	0.8600
C4—C1—C2	106.51 (18)	C4—C5—H5B	108.9
C4—C1—H1A	126.7	H5A—C5—H5B	107.7
C2—C1—H1A	126.7	O2—C6—N1	124.26 (14)
C3—C2—C1	106.82 (17)	O2—C6—C7	119.83 (13)
C3—C2—H2	126.6	N1—C6—C7	115.90 (12)
C1—C2—H2	126.6	C8—C7—C6	109.59 (13)
C2—C3—O1	110.29 (18)	C8—C7—H7A	109.8
C2—C3—H3	124.9	C6—C7—H7A	109.8
O1—C3—H3	124.9	C8—C7—H7B	109.8
C1—C4—O1	109.60 (15)	C6—C7—H7B	109.8
C1—C4—C5	134.05 (17)	H7A—C7—H7B	108.2
O1—C4—C5	116.34 (13)	N2—C8—C7	178.0 (2)
N1—C5—C4	113.30 (13)	C6—N1—C5	123.31 (12)
N1—C5—H5A	108.9	C6—N1—H1	118.3
C4—C5—H5A	108.9	C5—N1—H1	118.3
N1—C5—H5B	108.9	C3—O1—C4	106.78 (14)
C4—C1—C2—C3	−0.1 (2)	N1—C6—C7—C8	−125.10 (14)
C1—C2—C3—O1	0.5 (2)	O2—C6—N1—C5	−4.5 (2)
C2—C1—C4—O1	−0.39 (19)	C7—C6—N1—C5	175.82 (13)
C2—C1—C4—C5	−179.82 (17)	C4—C5—N1—C6	124.16 (16)
C1—C4—C5—N1	105.9 (2)	C2—C3—O1—C4	−0.7 (2)
O1—C4—C5—N1	−73.48 (17)	C1—C4—O1—C3	0.70 (18)
O2—C6—C7—C8	55.19 (19)	C5—C4—O1—C3	−179.76 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	1.99	2.846 (1)	175
C7—H7A···O2i	0.97	2.55	3.395 (2)	145

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1O2i	0.86	1.99	2.846(1)	175
C7H7AO2i	0.97	2.55	3.395(2)	145

Symmetry code: (i) .