Crystal structure of 2-cyano-N-(furan-2-ylmeth­yl)acetamide

Abstract

In the title compound, C₈H₈N₂O₂, the acetamide unit is inclined to the furan ring by 76.7 (1)°. In the crystal, mol­ecules 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 _r = 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) ų

• 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

• Δρ_max = 0.14 e Å⁻³

• Δρ_min = −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.

Supplementary Material

CCDC reference: 1404031

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

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) .

supplementary crystallographic information

S1. Structural commentary

Furan derivatives are gaining importance for their wide pharmacological activities like anti­bacterial, anti­tumor, anti-inflammatory, anti­fungal, and analgesic (Anupam et al., 2011). Acetamide derivatives have been shown to possess various biological properties, and recently, the synthesis and biological activities of some heterocyclic derivatives containing the acetamide moiety have been reported (Fallah-Tafti et al., 2011; Shams et al., 2011). In continuation of our work on the synthesis of acetamide derivatives (Jasinski et al., 2013), we report herein on the synthesis and crystal structure of the title compound.

The title molecule, Fig. 1, is Z-shaped. The furan ring (O1/C1—C4) is nearly perpendicular with the mean plane of the acetamide group (O2/N1/C6/C7) with a dihedral angle of 76.7 (1)°. The aceto­nitrile moiety is inclined to the mean plane of the acetamide group by 54 (6) °. The bond lengths and angles are close to those reported for a very similar structure, 2-cyano-N-furfuryl-3-(2-furyl)acryl­amide (Pomés Hernández et al., 1996).

The crystal packing is stabilized by N—H···O and C—H···O hydrogen bonds (Table 1 and Fig. 2). Atoms N1 and C7 act as donors to a bifurcated acceptor O-atom, O2, generating C(4) chains along the a-axis and, as a consequence, an R₂¹(6) ring is formed.

S2. Synthesis and crystallization

An equimolar mixture of furfuryl amine and ethyl cyano acetate were mixed in a conical flask and the mixture was heated under microwave irradiation at 700 W for 3 min with an inter­val of 20 seconds each time. The mixture was then poured to a beaker and cooled giving a solid whose size reduced, washed with ethanol. It was recrystallized from an acetone/water mixture (7:3), yielding colourless block-like crystals on slow evaporation of the solvent.

S3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The NH and C-bound H atoms were included in calculated positions and refined using a riding model: N—H = 0.86 Å, C—H = 0.93 - 0.97 Å with U_iso(H) = 1.2U_eq (N,C).

Figures

Fig. 1.

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

Fig. 2.

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).

Crystal data

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

Data collection

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

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

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.

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

	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)

Atomic displacement parameters (Ų)

	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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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

Symmetry code: (i) x+1, y, z.