The title compound, C
7H
9NO
5, was prepared by the nucleophilic substitution reaction of acryloyl chloride with aspartic acid. The asymmetric unit contains two molecules. In the crystal structure, intermolecular N—H
O and O—H
O hydrogen bonds link the molecules into a three-dimensional network, which may be effective in stabilizing the crystal structure.
Supporting information
CCDC reference: 633888
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.054
- wR factor = 0.157
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg.
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 ALERT type 3 Indicator that the structure quality may be low
0 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.
N-acryoylaspartic acid
top
Crystal data top
C7H9NO5 | Z = 4 |
Mr = 187.15 | F(000) = 392 |
Triclinic, P1 | Dx = 1.424 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1560 (16) Å | Cell parameters from 25 reflections |
b = 10.079 (2) Å | θ = 11–13° |
c = 11.084 (2) Å | µ = 0.12 mm−1 |
α = 90.16 (3)° | T = 294 K |
β = 94.17 (3)° | Plate, colorless |
γ = 104.99 (3)° | 0.40 × 0.30 × 0.10 mm |
V = 877.6 (3) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 2448 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.008 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
ω/2θ scans | h = −10→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.953, Tmax = 0.988 | l = 0→13 |
3434 measured reflections | 3 standard reflections every 200 reflections |
3433 independent reflections | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0853P)2 + 0.2474P] where P = (Fo2 + 2Fc2)/3 |
3433 reflections | (Δ/σ)max < 0.001 |
235 parameters | Δρmax = 0.25 e Å−3 |
2 restraints | Δρmin = −0.34 e Å−3 |
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 | −0.2120 (3) | 0.5594 (2) | 0.0427 (2) | 0.0647 (7) | |
O2 | 0.1320 (3) | 0.92418 (19) | 0.31801 (18) | 0.0537 (6) | |
H2C | 0.1529 | 1.0019 | 0.3477 | 0.081* | |
O3 | −0.0049 (3) | 1.01281 (18) | 0.17129 (17) | 0.0448 (5) | |
O4 | 0.3067 (3) | 0.9725 (2) | 0.0467 (2) | 0.0603 (6) | |
O5 | 0.4636 (3) | 0.8229 (2) | 0.0490 (2) | 0.0671 (7) | |
H5A | 0.5312 | 0.8871 | 0.0196 | 0.101* | |
N1 | −0.0692 (3) | 0.7816 (2) | 0.03214 (18) | 0.0365 (5) | |
H1A | −0.0517 | 0.8546 | −0.0102 | 0.044* | |
C1 | −0.4091 (5) | 0.5810 (3) | −0.1713 (3) | 0.0753 (11) | |
H1B | −0.4318 | 0.4959 | −0.1348 | 0.090* | |
H1C | −0.4712 | 0.5930 | −0.2423 | 0.090* | |
C2 | −0.2861 (3) | 0.6872 (3) | −0.1212 (2) | 0.0426 (6) | |
H2A | −0.2640 | 0.7721 | −0.1581 | 0.051* | |
C3 | −0.1871 (3) | 0.6702 (2) | −0.0094 (2) | 0.0373 (6) | |
C4 | 0.0304 (3) | 0.7844 (2) | 0.1455 (2) | 0.0343 (6) | |
H4A | −0.0356 | 0.7130 | 0.1955 | 0.041* | |
C5 | 0.0507 (3) | 0.9210 (2) | 0.2108 (2) | 0.0352 (6) | |
C6 | 0.2007 (3) | 0.7515 (3) | 0.1325 (2) | 0.0391 (6) | |
H6A | 0.2497 | 0.7376 | 0.2124 | 0.047* | |
H6B | 0.1804 | 0.6659 | 0.0867 | 0.047* | |
C7 | 0.3272 (3) | 0.8600 (3) | 0.0715 (2) | 0.0419 (6) | |
O6 | 1.2221 (2) | 0.15862 (19) | 0.44545 (18) | 0.0493 (5) | |
O7 | 1.0021 (3) | 0.51749 (19) | 0.32469 (18) | 0.0508 (5) | |
O8 | 0.8621 (3) | 0.3702 (2) | 0.17731 (18) | 0.0564 (6) | |
H8D | 0.8477 | 0.4403 | 0.1458 | 0.085* | |
O9 | 0.6782 (3) | 0.3262 (2) | 0.4319 (3) | 0.0736 (7) | |
O10 | 0.5240 (3) | 0.1121 (2) | 0.3949 (3) | 0.0753 (8) | |
H10A | 0.4457 | 0.1438 | 0.4128 | 0.113* | |
N2 | 1.0662 (3) | 0.3105 (2) | 0.46104 (19) | 0.0403 (5) | |
H2B | 1.0418 | 0.3720 | 0.5053 | 0.048* | |
C8 | 1.3796 (5) | 0.2431 (4) | 0.6800 (3) | 0.0701 (10) | |
H8A | 1.3944 | 0.1613 | 0.6495 | 0.084* | |
H8B | 1.4355 | 0.2797 | 0.7535 | 0.084* | |
C9 | 1.2773 (4) | 0.3086 (3) | 0.6176 (3) | 0.0477 (7) | |
H9A | 1.2634 | 0.3904 | 0.6490 | 0.057* | |
C10 | 1.1876 (3) | 0.2541 (2) | 0.5021 (2) | 0.0361 (6) | |
C11 | 0.9720 (3) | 0.2735 (2) | 0.3446 (2) | 0.0368 (6) | |
H11A | 1.0445 | 0.2362 | 0.2945 | 0.044* | |
C12 | 0.9470 (3) | 0.4016 (3) | 0.2835 (2) | 0.0385 (6) | |
C13 | 0.8067 (3) | 0.1621 (3) | 0.3500 (3) | 0.0429 (7) | |
H13A | 0.7702 | 0.1234 | 0.2692 | 0.051* | |
H13B | 0.8281 | 0.0892 | 0.4007 | 0.051* | |
C14 | 0.6657 (4) | 0.2112 (3) | 0.3980 (3) | 0.0469 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0705 (15) | 0.0334 (11) | 0.0746 (15) | −0.0058 (10) | −0.0279 (12) | 0.0139 (10) |
O2 | 0.0729 (15) | 0.0389 (11) | 0.0470 (12) | 0.0160 (10) | −0.0152 (10) | −0.0097 (9) |
O3 | 0.0581 (13) | 0.0348 (10) | 0.0449 (11) | 0.0185 (9) | 0.0018 (9) | −0.0007 (8) |
O4 | 0.0485 (12) | 0.0468 (12) | 0.0925 (17) | 0.0195 (10) | 0.0232 (11) | 0.0249 (11) |
O5 | 0.0539 (14) | 0.0618 (14) | 0.0983 (18) | 0.0300 (11) | 0.0333 (13) | 0.0291 (12) |
N1 | 0.0428 (13) | 0.0278 (10) | 0.0356 (11) | 0.0048 (9) | −0.0031 (9) | 0.0036 (8) |
C1 | 0.080 (3) | 0.054 (2) | 0.079 (3) | 0.0047 (18) | −0.037 (2) | −0.0044 (17) |
C2 | 0.0416 (15) | 0.0386 (15) | 0.0473 (16) | 0.0111 (12) | −0.0007 (12) | 0.0005 (12) |
C3 | 0.0379 (14) | 0.0285 (13) | 0.0442 (15) | 0.0070 (11) | 0.0002 (12) | −0.0005 (11) |
C4 | 0.0374 (14) | 0.0286 (12) | 0.0359 (13) | 0.0069 (10) | 0.0023 (11) | 0.0014 (10) |
C5 | 0.0365 (14) | 0.0321 (13) | 0.0360 (14) | 0.0063 (11) | 0.0054 (11) | 0.0007 (10) |
C6 | 0.0419 (15) | 0.0326 (13) | 0.0436 (15) | 0.0113 (11) | 0.0020 (12) | 0.0008 (11) |
C7 | 0.0386 (15) | 0.0457 (15) | 0.0431 (15) | 0.0143 (12) | 0.0033 (12) | 0.0032 (12) |
O6 | 0.0446 (11) | 0.0471 (11) | 0.0601 (12) | 0.0231 (9) | −0.0102 (9) | −0.0187 (9) |
O7 | 0.0675 (14) | 0.0359 (11) | 0.0491 (12) | 0.0159 (10) | −0.0028 (10) | −0.0008 (8) |
O8 | 0.0827 (16) | 0.0430 (11) | 0.0449 (12) | 0.0239 (11) | −0.0143 (11) | −0.0011 (9) |
O9 | 0.0621 (15) | 0.0555 (14) | 0.108 (2) | 0.0195 (12) | 0.0253 (14) | −0.0174 (13) |
O10 | 0.0454 (13) | 0.0568 (14) | 0.124 (2) | 0.0103 (11) | 0.0231 (14) | −0.0083 (14) |
N2 | 0.0473 (13) | 0.0407 (12) | 0.0377 (12) | 0.0216 (10) | −0.0020 (10) | −0.0076 (9) |
C8 | 0.073 (2) | 0.066 (2) | 0.071 (2) | 0.0269 (19) | −0.0299 (19) | −0.0178 (18) |
C9 | 0.0473 (17) | 0.0463 (16) | 0.0515 (17) | 0.0185 (13) | −0.0061 (13) | −0.0101 (13) |
C10 | 0.0347 (14) | 0.0319 (13) | 0.0419 (14) | 0.0100 (11) | −0.0004 (11) | −0.0024 (11) |
C11 | 0.0418 (15) | 0.0351 (13) | 0.0376 (14) | 0.0179 (11) | 0.0018 (11) | −0.0023 (10) |
C12 | 0.0437 (15) | 0.0385 (14) | 0.0365 (14) | 0.0163 (12) | 0.0035 (12) | −0.0006 (11) |
C13 | 0.0444 (16) | 0.0354 (14) | 0.0515 (16) | 0.0155 (12) | 0.0023 (13) | 0.0003 (12) |
C14 | 0.0446 (17) | 0.0455 (17) | 0.0538 (17) | 0.0173 (13) | 0.0038 (13) | 0.0025 (13) |
Geometric parameters (Å, º) top
O1—C3 | 1.235 (3) | O6—C10 | 1.249 (3) |
O2—C5 | 1.314 (3) | O7—C12 | 1.213 (3) |
O2—H2C | 0.8200 | O8—C12 | 1.315 (3) |
O3—C5 | 1.202 (3) | O8—H8D | 0.8200 |
O4—C7 | 1.218 (3) | O9—C14 | 1.195 (3) |
O5—C7 | 1.302 (3) | O10—C14 | 1.315 (4) |
O5—H5A | 0.8200 | O10—H10A | 0.8200 |
N1—C3 | 1.331 (3) | N2—C10 | 1.319 (3) |
N1—C4 | 1.441 (3) | N2—C11 | 1.449 (3) |
N1—H1A | 0.8600 | N2—H2B | 0.8600 |
C1—C2 | 1.349 (3) | C8—C9 | 1.347 (3) |
C1—H1B | 0.9300 | C8—H8A | 0.9300 |
C1—H1C | 0.9300 | C8—H8B | 0.9300 |
C2—C3 | 1.464 (4) | C9—C10 | 1.459 (4) |
C2—H2A | 0.9300 | C9—H9A | 0.9300 |
C4—C5 | 1.519 (3) | C11—C12 | 1.513 (3) |
C4—C6 | 1.526 (4) | C11—C13 | 1.520 (4) |
C4—H4A | 0.9800 | C11—H11A | 0.9800 |
C6—C7 | 1.497 (4) | C13—C14 | 1.494 (4) |
C6—H6A | 0.9700 | C13—H13A | 0.9700 |
C6—H6B | 0.9700 | C13—H13B | 0.9700 |
| | | |
C5—O2—H2C | 109.5 | C12—O8—H8D | 109.5 |
C7—O5—H5A | 109.5 | C14—O10—H10A | 109.5 |
C3—N1—C4 | 122.5 (2) | C10—N2—C11 | 122.8 (2) |
C3—N1—H1A | 118.8 | C10—N2—H2B | 118.6 |
C4—N1—H1A | 118.8 | C11—N2—H2B | 118.6 |
C2—C1—H1B | 120.0 | C9—C8—H8A | 120.0 |
C2—C1—H1C | 120.0 | C9—C8—H8B | 120.0 |
H1B—C1—H1C | 120.0 | H8A—C8—H8B | 120.0 |
C1—C2—C3 | 120.7 (3) | C8—C9—C10 | 121.5 (3) |
C1—C2—H2A | 119.6 | C8—C9—H9A | 119.3 |
C3—C2—H2A | 119.6 | C10—C9—H9A | 119.3 |
O1—C3—N1 | 122.4 (2) | O6—C10—N2 | 121.6 (2) |
O1—C3—C2 | 121.9 (2) | O6—C10—C9 | 122.3 (2) |
N1—C3—C2 | 115.7 (2) | N2—C10—C9 | 116.1 (2) |
N1—C4—C5 | 109.5 (2) | N2—C11—C12 | 109.5 (2) |
N1—C4—C6 | 113.6 (2) | N2—C11—C13 | 114.0 (2) |
C5—C4—C6 | 112.4 (2) | C12—C11—C13 | 112.8 (2) |
N1—C4—H4A | 107.0 | N2—C11—H11A | 106.6 |
C5—C4—H4A | 107.0 | C12—C11—H11A | 106.6 |
C6—C4—H4A | 107.0 | C13—C11—H11A | 106.6 |
O3—C5—O2 | 124.3 (2) | O7—C12—O8 | 124.7 (2) |
O3—C5—C4 | 124.4 (2) | O7—C12—C11 | 124.8 (2) |
O2—C5—C4 | 111.2 (2) | O8—C12—C11 | 110.5 (2) |
C7—C6—C4 | 114.4 (2) | C14—C13—C11 | 114.0 (2) |
C7—C6—H6A | 108.7 | C14—C13—H13A | 108.8 |
C4—C6—H6A | 108.7 | C11—C13—H13A | 108.8 |
C7—C6—H6B | 108.7 | C14—C13—H13B | 108.8 |
C4—C6—H6B | 108.7 | C11—C13—H13B | 108.8 |
H6A—C6—H6B | 107.6 | H13A—C13—H13B | 107.7 |
O4—C7—O5 | 123.1 (3) | O9—C14—O10 | 124.1 (3) |
O4—C7—C6 | 123.8 (2) | O9—C14—C13 | 124.6 (3) |
O5—C7—C6 | 113.1 (2) | O10—C14—C13 | 111.2 (2) |
| | | |
C4—N1—C3—O1 | −4.4 (4) | C11—N2—C10—O6 | −4.3 (4) |
C4—N1—C3—C2 | 175.4 (2) | C11—N2—C10—C9 | 176.4 (2) |
C1—C2—C3—O1 | 0.0 (5) | C8—C9—C10—O6 | −12.3 (5) |
C1—C2—C3—N1 | −179.9 (3) | C8—C9—C10—N2 | 167.0 (3) |
C3—N1—C4—C5 | −139.7 (2) | C10—N2—C11—C12 | −138.9 (2) |
C3—N1—C4—C6 | 93.8 (3) | C10—N2—C11—C13 | 93.6 (3) |
N1—C4—C5—O3 | −1.7 (3) | N2—C11—C12—O7 | 2.0 (4) |
C6—C4—C5—O3 | 125.5 (3) | C13—C11—C12—O7 | 130.2 (3) |
N1—C4—C5—O2 | 176.1 (2) | N2—C11—C12—O8 | 179.8 (2) |
C6—C4—C5—O2 | −56.7 (3) | C13—C11—C12—O8 | −52.0 (3) |
N1—C4—C6—C7 | 69.5 (3) | N2—C11—C13—C14 | 76.1 (3) |
C5—C4—C6—C7 | −55.5 (3) | C12—C11—C13—C14 | −49.7 (3) |
C4—C6—C7—O4 | 8.5 (4) | C11—C13—C14—O9 | −1.3 (4) |
C4—C6—C7—O5 | −172.5 (2) | C11—C13—C14—O10 | 176.9 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2C···O6i | 0.82 | 1.85 | 2.655 (3) | 166 |
O5—H5A···O4ii | 0.82 | 1.86 | 2.681 (3) | 177 |
N1—H1A···O3iii | 0.86 | 2.24 | 3.053 (3) | 159 |
O8—H8D···O1iv | 0.82 | 1.79 | 2.590 (3) | 164 |
O10—H10A···O6v | 0.82 | 1.93 | 2.719 (3) | 162 |
N2—H2B···O7vi | 0.86 | 2.28 | 3.102 (3) | 159 |
Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y+2, −z; (iii) −x, −y+2, −z; (iv) x+1, y, z; (v) x−1, y, z; (vi) −x+2, −y+1, −z+1. |