The title compound, C
6H
9NO
3, was prepared by a nucleophilic substitution reaction of acryloyl chloride with
L-alanine. In the crystal structure, intermolecular N—H
O and O—H
O hydrogen bonds link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the crystal structure.
Supporting information
CCDC reference: 633887
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.082
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
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 25.97
From the CIF: _reflns_number_total 888
Count of symmetry unique reflns 889
Completeness (_total/calc) 99.89%
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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
0 ALERT type 5 Informative message, check
Data collection: CAD-4 Software (Enraf–Nonius, 1985); 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.
Crystal data top
C6H9NO3 | F(000) = 304 |
Mr = 143.14 | Dx = 1.251 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 8.3670 (17) Å | θ = 11–13° |
b = 8.7730 (18) Å | µ = 0.10 mm−1 |
c = 10.350 (2) Å | T = 294 K |
V = 759.7 (3) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.30 × 0.30 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 805 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 26.0°, θmin = 3.0° |
ω/2θ scans | h = −10→0 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→0 |
Tmin = 0.962, Tmax = 0.972 | l = −12→12 |
1686 measured reflections | 3 standard reflections every 200 reflections |
888 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.05P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
888 reflections | Δρmax = 0.18 e Å−3 |
92 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.317 (19) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.09773 (18) | 0.63916 (19) | 0.91853 (16) | 0.0617 (5) | |
O2 | 0.15140 (17) | 0.96009 (17) | 0.78132 (14) | 0.0522 (4) | |
O3 | 0.13615 (18) | 0.57691 (18) | 0.71336 (14) | 0.0569 (5) | |
H3 | 0.0454 | 0.5425 | 0.7197 | 0.085* | |
N1 | 0.34804 (18) | 0.85087 (17) | 0.89286 (15) | 0.0403 (4) | |
H1 | 0.4156 | 0.8568 | 0.9553 | 0.048* | |
C1 | 0.2072 (3) | 1.2358 (2) | 0.9254 (3) | 0.0691 (7) | |
H1A | 0.1462 | 1.2468 | 0.8509 | 0.083* | |
H1B | 0.2225 | 1.3186 | 0.9801 | 0.083* | |
C2 | 0.2716 (3) | 1.1042 (2) | 0.9532 (2) | 0.0504 (5) | |
H2 | 0.3322 | 1.0955 | 1.0282 | 0.060* | |
C3 | 0.2516 (2) | 0.9678 (2) | 0.86977 (17) | 0.0396 (5) | |
C4 | 0.3424 (2) | 0.7135 (2) | 0.81552 (18) | 0.0393 (5) | |
H4 | 0.3669 | 0.7393 | 0.7255 | 0.047* | |
C5 | 0.4649 (3) | 0.5992 (3) | 0.8644 (3) | 0.0584 (6) | |
H5A | 0.5697 | 0.6435 | 0.8601 | 0.088* | |
H5B | 0.4616 | 0.5092 | 0.8116 | 0.088* | |
H5C | 0.4409 | 0.5726 | 0.9522 | 0.088* | |
C6 | 0.1766 (2) | 0.6428 (2) | 0.82196 (18) | 0.0378 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0531 (9) | 0.0769 (11) | 0.0552 (8) | −0.0180 (8) | 0.0200 (7) | −0.0147 (8) |
O2 | 0.0489 (8) | 0.0579 (8) | 0.0498 (8) | 0.0137 (7) | −0.0146 (7) | −0.0049 (7) |
O3 | 0.0494 (8) | 0.0748 (10) | 0.0466 (8) | −0.0176 (8) | 0.0013 (7) | −0.0140 (7) |
N1 | 0.0362 (8) | 0.0420 (8) | 0.0427 (8) | −0.0015 (7) | −0.0112 (7) | 0.0016 (7) |
C1 | 0.0922 (18) | 0.0456 (12) | 0.0696 (14) | 0.0011 (13) | −0.0069 (15) | −0.0052 (12) |
C2 | 0.0560 (13) | 0.0480 (11) | 0.0472 (11) | −0.0055 (10) | −0.0046 (10) | −0.0017 (10) |
C3 | 0.0360 (9) | 0.0444 (11) | 0.0384 (9) | −0.0004 (9) | −0.0011 (8) | 0.0056 (9) |
C4 | 0.0345 (9) | 0.0454 (10) | 0.0380 (9) | 0.0010 (8) | 0.0020 (8) | 0.0004 (8) |
C5 | 0.0443 (10) | 0.0563 (12) | 0.0747 (14) | 0.0117 (10) | −0.0028 (11) | −0.0074 (13) |
C6 | 0.0355 (9) | 0.0375 (9) | 0.0406 (9) | 0.0001 (8) | 0.0018 (8) | −0.0016 (8) |
Geometric parameters (Å, º) top
N1—C3 | 1.327 (2) | O2—C3 | 1.243 (2) |
N1—C4 | 1.447 (2) | O3—C6 | 1.309 (2) |
N1—H1 | 0.8600 | O3—H3 | 0.8200 |
C1—C2 | 1.307 (3) | C4—C6 | 1.521 (2) |
C1—H1A | 0.9300 | C4—C5 | 1.521 (3) |
C1—H1B | 0.9300 | C4—H4 | 0.9800 |
O1—C6 | 1.198 (2) | C5—H5A | 0.9600 |
C2—C3 | 1.485 (3) | C5—H5B | 0.9600 |
C2—H2 | 0.9300 | C5—H5C | 0.9600 |
| | | |
C3—N1—C4 | 121.60 (15) | N1—C4—C5 | 110.07 (16) |
C3—N1—H1 | 119.2 | C6—C4—C5 | 109.35 (16) |
C4—N1—H1 | 119.2 | N1—C4—H4 | 109.1 |
C2—C1—H1A | 120.0 | C6—C4—H4 | 109.1 |
C2—C1—H1B | 120.0 | C5—C4—H4 | 109.1 |
H1A—C1—H1B | 120.0 | C4—C5—H5A | 109.5 |
C1—C2—C3 | 122.5 (2) | C4—C5—H5B | 109.5 |
C1—C2—H2 | 118.7 | H5A—C5—H5B | 109.5 |
C3—C2—H2 | 118.7 | C4—C5—H5C | 109.5 |
C6—O3—H3 | 109.5 | H5A—C5—H5C | 109.5 |
O2—C3—N1 | 120.06 (18) | H5B—C5—H5C | 109.5 |
O2—C3—C2 | 123.21 (17) | O1—C6—O3 | 124.20 (17) |
N1—C3—C2 | 116.73 (17) | O1—C6—C4 | 123.36 (18) |
N1—C4—C6 | 110.20 (15) | O3—C6—C4 | 112.24 (16) |
| | | |
C4—N1—C3—O2 | 1.2 (3) | C3—N1—C4—C5 | −179.64 (18) |
C4—N1—C3—C2 | −178.35 (17) | N1—C4—C6—O1 | −38.8 (3) |
C1—C2—C3—O2 | −13.2 (4) | C5—C4—C6—O1 | 82.3 (2) |
C1—C2—C3—N1 | 166.4 (2) | N1—C4—C6—O3 | 146.07 (16) |
C3—N1—C4—C6 | −59.0 (2) | C5—C4—C6—O3 | −92.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.01 | 2.861 (2) | 171 |
O3—H3···O2ii | 0.82 | 1.80 | 2.616 (2) | 175 |
Symmetry codes: (i) x+1/2, −y+3/2, −z+2; (ii) −x, y−1/2, −z+3/2. |