Acrylamide

In the crystal structure of the title compound, C₃H₅NO, the mol­ecules are linked through N—H...O hydrogen bonds, forming a two-dimensional supra­molecular network.

Key indicators

• Single-crystal X-ray study
• T = 113 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.107
• Data-to-parameter ratio = 17.5

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S1. Comment

In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).

The expected geometric parameters are observed in (I) (Fig. 1). The molecules are linked through N—H···O hydrogen bonds (Table 2), forming a two-dimensional supramolecular network which leads to stable crystal structure. Fig. 2 shows a portion of this extensively hydrogen-bonded supramolecular assembly.

Related literature

For related literature, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).

S2. Experimental

Acrylamide (1 g) was added to a Trichloro-methane (50 ml), with stirring at 350 K. The resulting colourless solution was filtered and the filtrate was allowed to stand in air at room temperature for 10 d, yielding colourless crystals of (I).

S3. Refinement

The H atoms of the NH₂ group were found from a difference Fourier map and refined freely. C-bound H atoms were placed in calculated positions with C—H = 0.93 Å and refined using a riding model, with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I), viewed down the a axis. Hydrogen bonds are indicated by dashed lines.

Acrylamide

Crystal data

C3H5NO	F(000) = 152
Mr = 71.08	Dx = 1.187 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1254 reflections
a = 8.2062 (16) Å	θ = 2.3–25.0°
b = 5.7480 (11) Å	µ = 0.09 mm^−1
c = 9.0527 (18) Å	T = 113 K
β = 111.37 (3)°	Block, colourless
V = 397.65 (16) Å^3	0.10 × 0.08 × 0.06 mm
Z = 4

Data collection

Rigaku Saturn diffractometer	943 independent reflections
Radiation source: rotating anode	832 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.030
Detector resolution: 7.31 pixels mm^-1	θmax = 27.9°, θmin = 2.9°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→7
Tmin = 0.991, Tmax = 0.995	l = −11→11
2936 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0533P)^2 + 0.053P] where P = (Fo^2 + 2Fc^2)/3
943 reflections	(Δ/σ)max < 0.001
54 parameters	Δρmax = 0.20 e Å^−3
3 restraints	Δρmin = −0.19 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
O1	0.01963 (11)	0.26267 (14)	0.86873 (9)	0.0303 (3)
N1	0.21481 (13)	0.36721 (18)	1.10725 (11)	0.0281 (3)
C1	0.15782 (14)	0.2263 (2)	0.98265 (12)	0.0226 (3)
C2	0.26969 (15)	0.0222 (2)	0.98707 (13)	0.0283 (3)
H2	0.3754	0.0058	1.0719	0.034*
C3	0.22422 (19)	−0.1360 (2)	0.87512 (16)	0.0383 (4)
H3A	0.1189	−0.1220	0.7896	0.046*
H3B	0.2972	−0.2623	0.8812	0.046*
H1A	0.3147 (13)	0.344 (2)	1.1876 (13)	0.032 (3)*
H1B	0.1520 (16)	0.492 (2)	1.1129 (17)	0.041 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0228 (4)	0.0377 (6)	0.0219 (4)	0.0031 (3)	−0.0021 (3)	−0.0051 (3)
N1	0.0226 (5)	0.0298 (6)	0.0221 (5)	0.0056 (4)	−0.0034 (4)	−0.0023 (4)
C1	0.0191 (5)	0.0277 (6)	0.0189 (5)	−0.0011 (4)	0.0045 (4)	0.0016 (4)
C2	0.0284 (6)	0.0317 (7)	0.0256 (6)	0.0058 (5)	0.0109 (5)	0.0057 (5)
C3	0.0482 (8)	0.0314 (7)	0.0399 (7)	0.0052 (6)	0.0215 (7)	0.0008 (5)

Geometric parameters (Å, º)

O1—C1	1.2413 (14)	C2—C3	1.3106 (18)
N1—C1	1.3275 (14)	C2—H2	0.9300
N1—H1A	0.886 (8)	C3—H3A	0.9300
N1—H1B	0.894 (8)	C3—H3B	0.9300
C1—C2	1.4815 (16)
C1—N1—H1A	122.6 (9)	C3—C2—C1	121.98 (12)
C1—N1—H1B	120.3 (9)	C3—C2—H2	119.0
H1A—N1—H1B	117.1 (11)	C1—C2—H2	119.0
O1—C1—N1	122.39 (11)	C2—C3—H3A	120.0
O1—C1—C2	121.69 (10)	C2—C3—H3B	120.0
N1—C1—C2	115.93 (10)	H3A—C3—H3B	120.0
O1—C1—C2—C3	−3.48 (18)	N1—C1—C2—C3	176.71 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.89 (1)	1.97 (1)	2.8465 (16)	170 (1)
N1—H1B···O1^ii	0.89 (1)	2.04 (1)	2.9291 (13)	171 (2)

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