N-Acryloylglycine

In the crystal structure of the title compound, C₅H₇NO₃, inter­molecular hydrogen bonds, link the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.102
• Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.66
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.42

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.02
           From the CIF: _reflns_number_total                666
           Count of symmetry unique reflns          668
           Completeness (_total/calc)             99.70%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; 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.

N-Acryloyl glycine

Crystal data

C5H7NO3	Dx = 1.365 Mg m^−3
Mr = 129.12	Melting point: 401 K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 25 reflections
a = 18.212 (4) Å	θ = 10–12°
b = 18.318 (4) Å	µ = 0.11 mm^−1
c = 7.5330 (15) Å	T = 294 K
V = 2513.0 (9) Å^3	Block, colorless
Z = 16	0.30 × 0.20 × 0.10 mm
F(000) = 1088

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.054
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 3.1°
Graphite monochromator	h = −22→0
ω scans	k = −22→22
1307 measured reflections	l = 0→9
666 independent reflections	3 standard reflections every 200 reflections
614 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.5439P] where P = (Fo^2 + 2Fc^2)/3
666 reflections	(Δ/σ)max < 0.001
87 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.34 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
C1	0.13765 (13)	0.17628 (12)	0.2606 (4)	0.0366 (6)
C2	0.18236 (12)	0.10849 (13)	0.2338 (4)	0.0396 (6)
H2A	0.1881	0.0834	0.3464	0.047*
H2B	0.1569	0.0760	0.1528	0.047*
C3	0.29783 (12)	0.07597 (13)	0.0921 (4)	0.0380 (6)
C4	0.37050 (15)	0.10227 (16)	0.0293 (4)	0.0467 (6)
H4	0.3798	0.1522	0.0274	0.056*
C5	0.42144 (16)	0.05757 (19)	−0.0232 (6)	0.0654 (10)
H5A	0.4130	0.0075	−0.0222	0.079*
H5B	0.4664	0.0756	−0.0619	0.079*
N1	0.25391 (11)	0.12621 (10)	0.1625 (4)	0.0402 (5)
O1	0.15986 (10)	0.23722 (9)	0.2332 (3)	0.0569 (6)
O2	0.07119 (10)	0.16096 (9)	0.3184 (3)	0.0481 (6)
H2	0.0475	0.1988	0.3284	0.072*
O3	0.28002 (10)	0.01096 (9)	0.0815 (4)	0.0576 (6)
H1	0.2688 (17)	0.1728 (17)	0.174 (5)	0.055 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0303 (11)	0.0281 (11)	0.0514 (14)	0.0012 (9)	−0.0015 (11)	−0.0023 (10)
C2	0.0297 (11)	0.0274 (10)	0.0616 (15)	0.0009 (9)	−0.0011 (14)	−0.0003 (11)
C3	0.0303 (12)	0.0304 (10)	0.0531 (14)	0.0003 (9)	−0.0059 (11)	−0.0058 (11)
C4	0.0368 (13)	0.0407 (13)	0.0625 (15)	−0.0057 (11)	0.0012 (13)	−0.0034 (12)
C5	0.0375 (14)	0.0564 (17)	0.103 (3)	−0.0034 (14)	0.0145 (18)	−0.0052 (19)
N1	0.0314 (10)	0.0272 (9)	0.0620 (12)	−0.0003 (7)	0.0012 (10)	−0.0049 (10)
O1	0.0433 (9)	0.0254 (8)	0.1019 (16)	−0.0019 (7)	0.0175 (12)	0.0001 (10)
O2	0.0313 (9)	0.0300 (8)	0.0831 (15)	−0.0002 (7)	0.0085 (10)	−0.0008 (9)
O3	0.0339 (9)	0.0321 (9)	0.1068 (17)	−0.0044 (7)	0.0057 (12)	−0.0219 (12)

Geometric parameters (Å, º)

C1—O1	1.205 (3)	C3—C4	1.486 (4)
C1—O2	1.317 (3)	C4—C5	1.299 (4)
C1—C2	1.498 (3)	C4—H4	0.9300
C2—N1	1.446 (3)	C5—H5A	0.9300
C2—H2A	0.9700	C5—H5B	0.9300
C2—H2B	0.9700	N1—H1	0.90 (3)
C3—O3	1.237 (3)	O2—H2	0.8200
C3—N1	1.330 (3)
O1—C1—O2	124.2 (2)	N1—C3—C4	116.0 (2)
O1—C1—C2	124.2 (2)	C5—C4—C3	121.9 (3)
O2—C1—C2	111.55 (19)	C5—C4—H4	119.0
N1—C2—C1	110.70 (19)	C3—C4—H4	119.0
N1—C2—H2A	109.5	C4—C5—H5A	120.0
C1—C2—H2A	109.5	C4—C5—H5B	120.0
N1—C2—H2B	109.5	H5A—C5—H5B	120.0
C1—C2—H2B	109.5	C3—N1—C2	122.3 (2)
H2A—C2—H2B	108.1	C3—N1—H1	121 (2)
O3—C3—N1	122.3 (2)	C2—N1—H1	117 (2)
O3—C3—C4	121.7 (2)	C1—O2—H2	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.90 (3)	2.35 (3)	2.712 (3)	104 (2)
N1—H1···O1^i	0.90 (3)	2.14 (3)	3.001 (3)	159.00
C2—H2A···O3^ii	0.97	2.54	3.481 (4)	163

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