N-Acryloylglycylglycine monohydrate

The title compound [systematic name: 2-(2-acrylamido­acetamido)­acetic acid monohydrate], C₇H₁₀N₂O₄·H₂O, was prepared by the nucleophilic substitution reaction of acryloyl chloride with glycylglycine. Excluding H atoms, the main chain of the mol­ecule is nearly planar. In the crystal structure, O—H...O, N—H...O and C—H...O hydrogen bonds link the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.053
• wR factor = 0.163
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.85 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.28
PLAT415_ALERT_2_C Short Inter D-H..H-X       H1B    ..  HWB     ..       2.10 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

N-acryloylglycylglycine(I) is one of the useful synthetic intermediates and free radical addition monomers. The crystal structure determination of the title compound, (I), has been carried out in order to elucidate its molecular conformation.

In the molecule of the title compound, (I), (Fig.1) the bond lengths and angles are within normal ranges (Allen et al., 1987). The main chain of the molecule is nearly planar.

In the crystal structure, O—H···O, N—H···O and C—H···O hydrogen bonds (Table 1) link the molecules into a three dimensional network, in which they may be effective in the stabilization of the structure.

Related literature

For bond-length data, see: Allen et al. (1987).

S2. Experimental

For the preparation of the title compound, acryloyl chloride (1.1 ml) containing diphenylpicrylhydrazyl polymerization inhibitor (0.01%) and sodium hydroxide solution [0.61 g, in H₂O (5 ml)] were added dropwise simultaneously over a 30 min period to a well stirred aqueous solution of glycylglycine [2.0 g, in H₂O (30 ml)] and sodium hydroxide [0.61 g, in H₂O (5 ml)], and then stirred 1 h more. The reaction of the mixture was kept at 273 K in an ice-water bath. The solution was acidified to pH = 2 with 6 N HCl and the resulting solid was filtered off and crystallized from ethanol (95%) (yield; 63%, m.p. 421–423 K).

S3. Refinement

H atoms (for H₂O) were located in difference syntheses and constrained to ride on their parent atom [O—H = 0.8543, 0.8553 Å and U_iso(H) = 1.2U_eq(O)]. The remaining H atoms were positioned geometrically, with N—H = 0.86 Å (for NH), O—H = 0.82 Å (for OH) and C—H = 0.93, 0.93 and 0.97 Å, for aromatic and methylene H atoms and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C,N,O), where x = 1.5 for OH H and x = 1.2 for all other H atoms.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

2-(2-acrylamidoacetamido)acetic acid monohydrate

Crystal data

C7H10N2O4·H2O	F(000) = 432
Mr = 204.19	Dx = 1.403 Mg m^−3
Monoclinic, P21/n	Melting point: 422 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.332 (3) Å	Cell parameters from 25 reflections
b = 5.149 (1) Å	θ = 9–13°
c = 14.458 (3) Å	µ = 0.12 mm^−1
β = 103.09 (3)°	T = 294 K
V = 966.7 (4) Å^3	Block, colorless
Z = 4	0.40 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1424 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 25.9°, θmin = 1.9°
ω/2θ scans	h = 0→16
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
Tmin = 0.954, Tmax = 0.988	l = −17→17
1959 measured reflections	3 standard reflections every 120 min
1875 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.163	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 0.2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
1875 reflections	Δρmax = 0.20 e Å^−3
127 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Extinction correction: SHELXL97
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (5)

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
OW	0.23119 (13)	1.4675 (4)	0.32683 (15)	0.0778 (7)
HWA	0.1700	1.5204	0.3028	0.093*
HWB	0.2821	1.5271	0.3067	0.093*
O1	−0.09533 (11)	0.1547 (3)	0.75924 (12)	0.0549 (5)
O2	0.22255 (11)	0.4246 (3)	0.68108 (11)	0.0471 (4)
O3	0.26156 (12)	1.1329 (4)	0.45810 (13)	0.0596 (5)
H3A	0.2427	1.2454	0.4178	0.089*
O4	0.09464 (11)	1.1214 (3)	0.46083 (12)	0.0524 (5)
N1	0.06626 (12)	0.2081 (4)	0.73869 (12)	0.0394 (4)
H1A	0.1293	0.1580	0.7550	0.047*
N2	0.12573 (12)	0.7266 (3)	0.59002 (12)	0.0401 (5)
H2A	0.0655	0.7923	0.5697	0.048*
C1	−0.0148 (2)	−0.2397 (8)	0.8963 (3)	0.1003 (14)
H1B	−0.0855	−0.2131	0.8852	0.120*
H1C	0.0166	−0.3632	0.9403	0.120*
C2	0.03980 (18)	−0.1049 (5)	0.85048 (17)	0.0520 (6)
H2B	0.1103	−0.1356	0.8630	0.062*
C3	−0.00320 (16)	0.0949 (4)	0.77944 (15)	0.0392 (5)
C4	0.03959 (15)	0.4106 (4)	0.66844 (15)	0.0408 (5)
H4A	0.0015	0.5463	0.6919	0.049*
H4B	−0.0036	0.3403	0.6107	0.049*
C5	0.13773 (14)	0.5225 (4)	0.64742 (14)	0.0352 (5)
C6	0.21375 (16)	0.8398 (5)	0.56131 (17)	0.0463 (6)
H6A	0.2508	0.7044	0.5363	0.056*
H6B	0.2601	0.9146	0.6164	0.056*
C7	0.18165 (15)	1.0451 (4)	0.48762 (15)	0.0386 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
OW	0.0528 (11)	0.0893 (15)	0.1042 (16)	0.0224 (10)	0.0447 (10)	0.0482 (13)
O1	0.0335 (8)	0.0620 (11)	0.0732 (11)	0.0044 (7)	0.0204 (7)	0.0196 (9)
O2	0.0321 (8)	0.0464 (9)	0.0635 (10)	0.0015 (7)	0.0121 (7)	0.0119 (8)
O3	0.0356 (9)	0.0713 (12)	0.0752 (12)	0.0008 (8)	0.0194 (8)	0.0283 (10)
O4	0.0324 (9)	0.0629 (11)	0.0634 (10)	0.0051 (7)	0.0144 (7)	0.0182 (8)
N1	0.0292 (9)	0.0432 (10)	0.0472 (9)	−0.0002 (7)	0.0116 (7)	0.0040 (8)
N2	0.0290 (9)	0.0410 (10)	0.0515 (10)	0.0013 (7)	0.0116 (7)	0.0072 (8)
C1	0.0625 (19)	0.128 (3)	0.117 (3)	0.017 (2)	0.0358 (19)	0.078 (3)
C2	0.0392 (12)	0.0551 (15)	0.0633 (15)	0.0032 (10)	0.0147 (11)	0.0164 (12)
C3	0.0325 (10)	0.0421 (12)	0.0456 (11)	−0.0012 (9)	0.0141 (9)	0.0001 (9)
C4	0.0332 (11)	0.0448 (12)	0.0457 (11)	−0.0024 (9)	0.0114 (9)	0.0029 (10)
C5	0.0295 (10)	0.0375 (11)	0.0389 (10)	−0.0028 (8)	0.0088 (8)	−0.0052 (9)
C6	0.0320 (11)	0.0467 (13)	0.0614 (13)	0.0004 (9)	0.0130 (9)	0.0124 (11)
C7	0.0308 (10)	0.0410 (11)	0.0453 (12)	−0.0047 (9)	0.0116 (8)	−0.0014 (9)

Geometric parameters (Å, º)

OW—HWA	0.8553	N2—H2A	0.8600
OW—HWB	0.8543	C1—C2	1.292 (4)
O1—C3	1.235 (3)	C1—H1B	0.9300
O2—C5	1.233 (2)	C1—H1C	0.9300
O3—C7	1.314 (2)	C2—C3	1.475 (3)
O3—H3A	0.8200	C2—H2B	0.9300
O4—C7	1.203 (2)	C4—C5	1.522 (3)
N1—C3	1.338 (3)	C4—H4A	0.9700
N1—C4	1.443 (3)	C4—H4B	0.9700
N1—H1A	0.8600	C6—C7	1.493 (3)
N2—C5	1.326 (3)	C6—H6A	0.9700
N2—C6	1.452 (3)	C6—H6B	0.9700
HWA—OW—HWB	120.4	N1—C4—H4A	109.8
C3—N1—C4	122.67 (17)	C5—C4—H4A	109.8
C3—N1—H1A	118.7	N1—C4—H4B	109.8
C4—N1—H1A	118.7	C5—C4—H4B	109.8
C2—C1—H1B	120.0	H4A—C4—H4B	108.3
C2—C1—H1C	120.0	O2—C5—N2	122.73 (18)
H1B—C1—H1C	120.0	O2—C5—C4	121.30 (19)
C5—N2—C6	120.40 (17)	N2—C5—C4	115.96 (17)
C5—N2—H2A	119.8	N2—C6—C7	111.62 (18)
C6—N2—H2A	119.8	N2—C6—H6A	109.3
C1—C2—C3	123.8 (2)	C7—C6—H6A	109.3
C1—C2—H2B	118.1	N2—C6—H6B	109.3
C3—C2—H2B	118.1	C7—C6—H6B	109.3
C7—O3—H3A	109.5	H6A—C6—H6B	108.0
O1—C3—N1	122.5 (2)	O4—C7—O3	125.2 (2)
O1—C3—C2	123.19 (19)	O4—C7—C6	124.11 (19)
N1—C3—C2	114.31 (18)	O3—C7—C6	110.66 (18)
N1—C4—C5	109.16 (16)
C4—N1—C3—O1	0.5 (3)	C6—N2—C5—C4	−176.70 (19)
C4—N1—C3—C2	−179.1 (2)	N1—C4—C5—O2	6.8 (3)
C1—C2—C3—O1	1.7 (5)	N1—C4—C5—N2	−174.33 (17)
C1—C2—C3—N1	−178.6 (3)	C5—N2—C6—C7	172.89 (18)
C3—N1—C4—C5	171.95 (18)	N2—C6—C7—O4	5.4 (3)
C6—N2—C5—O2	2.2 (3)	N2—C6—C7—O3	−175.83 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···O1^i	0.86	2.05	2.755 (3)	140
N1—H1A···O2^ii	0.86	2.32	3.150 (2)	163
N2—H2A···O4^i	0.86	2.13	2.968 (2)	166
C2—H2B···O2^ii	0.93	2.47	3.305 (3)	149

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1/2, y−1/2, −z+3/2.