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The title compound, expected to be a betaine, 4-hydroxypyridinioacetate, HOC
5H
4N
+CH
2CO
2− or C
7H
7NO
3, on the basis of its synthesis by the nucleophilic displacement of chloride from the chloroacetate ion in water, exists as (4-oxo-1,4-dihydropyridin-1-yl)acetic acid. The acid H atom interacts with the oxo O atom of an adjacent molecule to form a linear helical chain [O
O = 2.451 (3) Å].
Supporting information
CCDC reference: 242328
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.044
- wR factor = 0.146
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for O1 - C1 .. 18.28 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C5 .. 11.25 su
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 5.93 su
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O3
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 27.50
From the CIF: _reflns_number_total 945
Count of symmetry unique reflns 951
Completeness (_total/calc) 99.37%
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
2 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
(4-Oxo-1,4-dihydropyridin-1-yl)acetic acid
top
Crystal data top
C7H7NO3 | F(000) = 320 |
Mr = 153.14 | Dx = 1.484 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6039 reflections |
a = 4.7413 (17) Å | θ = 4.5–27.3° |
b = 9.595 (5) Å | µ = 0.12 mm−1 |
c = 15.069 (7) Å | T = 293 K |
V = 685.5 (5) Å3 | Prism, yellow |
Z = 4 | 0.32 × 0.25 × 0.20 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 945 independent reflections |
Radiation source: fine-focus sealed tube | 857 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −6→5 |
Tmin = 0.963, Tmax = 0.977 | k = −12→12 |
6046 measured reflections | l = −19→19 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0871P)2 + 0.1698P] where P = (Fo2 + 2Fc2)/3 |
945 reflections | (Δ/σ)max = 0.001 |
101 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.1616 (5) | 0.6560 (2) | 0.6131 (2) | 0.0584 (6) | |
O2 | 0.8553 (5) | 0.4920 (3) | 0.5715 (1) | 0.0645 (7) | |
O3 | 0.6411 (5) | 0.2388 (2) | 0.2267 (1) | 0.0506 (6) | |
N1 | 1.0913 (5) | 0.4646 (2) | 0.4077 (2) | 0.0432 (6) | |
C1 | 1.0631 (6) | 0.5640 (3) | 0.5603 (2) | 0.0404 (6) | |
C2 | 1.2403 (7) | 0.5460 (3) | 0.4760 (2) | 0.0519 (8) | |
C3 | 1.1232 (7) | 0.3239 (3) | 0.4024 (2) | 0.0473 (7) | |
C4 | 0.9744 (7) | 0.2474 (3) | 0.3430 (2) | 0.0458 (7) | |
C5 | 0.7811 (6) | 0.3124 (3) | 0.2848 (2) | 0.0409 (6) | |
C6 | 0.7482 (7) | 0.4585 (3) | 0.2935 (2) | 0.0432 (6) | |
C7 | 0.9035 (7) | 0.5294 (3) | 0.3544 (2) | 0.0454 (7) | |
H1 | 1.0401 | 0.6777 | 0.6493 | 0.070* | |
H2a | 1.2868 | 0.6371 | 0.4523 | 0.062* | |
H2b | 1.4154 | 0.4993 | 0.4910 | 0.062* | |
H3 | 1.2494 | 0.2794 | 0.4402 | 0.057* | |
H4 | 0.9997 | 0.1513 | 0.3405 | 0.055* | |
H6 | 0.6206 | 0.5058 | 0.2575 | 0.052* | |
H7 | 0.8798 | 0.6253 | 0.3595 | 0.054* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.058 (1) | 0.061 (1) | 0.056 (1) | −0.016 (1) | −0.014 (1) | 0.018 (1) |
O2 | 0.063 (1) | 0.080 (2) | 0.050 (1) | −0.031 (1) | −0.013 (1) | 0.011 (1) |
O3 | 0.063 (1) | 0.041 (1) | 0.048 (1) | −0.003 (1) | 0.008 (1) | 0.003 (1) |
N1 | 0.047 (1) | 0.047 (1) | 0.036 (1) | −0.002 (1) | −0.004 (1) | 0.002 (1) |
C1 | 0.044 (1) | 0.039 (1) | 0.039 (1) | −0.005 (1) | −0.001 (1) | −0.003 (1) |
C2 | 0.055 (2) | 0.059 (2) | 0.042 (1) | −0.015 (2) | −0.004 (1) | 0.006 (1) |
C3 | 0.051 (2) | 0.050 (1) | 0.041 (1) | 0.010 (1) | 0.001 (1) | −0.003 (1) |
C4 | 0.055 (2) | 0.036 (1) | 0.047 (1) | 0.009 (1) | 0.003 (1) | −0.002 (1) |
C5 | 0.051 (2) | 0.037 (1) | 0.035 (1) | 0.002 (1) | −0.005 (1) | −0.001 (1) |
C6 | 0.051 (1) | 0.038 (1) | 0.041 (1) | 0.005 (1) | 0.001 (1) | −0.004 (1) |
C7 | 0.058 (2) | 0.036 (1) | 0.043 (1) | 0.001 (1) | −0.007 (1) | 0.001 (1) |
Geometric parameters (Å, º) top
O1—C1 | 1.276 (3) | C5—C6 | 1.417 (4) |
O2—C1 | 1.215 (4) | C6—C7 | 1.359 (4) |
O3—C5 | 1.306 (3) | O1—H1 | 0.82 |
N1—C2 | 1.473 (4) | C2—H2a | 0.97 |
N1—C3 | 1.360 (4) | C2—H2b | 0.97 |
N1—C7 | 1.351 (4) | C3—H3 | 0.93 |
C1—C2 | 1.533 (4) | C4—H4 | 0.93 |
C3—C4 | 1.356 (4) | C6—H6 | 0.93 |
C4—C5 | 1.414 (4) | C7—H7 | 0.93 |
| | | |
C2—N1—C3 | 120.9 (3) | C1—O1—H1 | 109.5 |
C2—N1—C7 | 119.2 (2) | N1—C2—H2a | 109.2 |
C3—N1—C7 | 119.7 (3) | C1—C2—H2a | 109.2 |
O1—C1—O2 | 127.1 (3) | N1—C2—H2b | 109.2 |
O1—C1—C2 | 113.2 (2) | C1—C2—H2b | 109.2 |
O2—C1—C2 | 119.6 (2) | H2a—C2—H2b | 107.9 |
N1—C2—C1 | 112.1 (2) | C4—C3—H3 | 119.4 |
N1—C3—C4 | 121.2 (3) | N1—C3—H3 | 119.4 |
C3—C4—C5 | 120.5 (2) | C3—C4—H4 | 119.7 |
O3—C5—C4 | 120.4 (2) | C5—C4—H4 | 119.7 |
O3—C5—C6 | 122.8 (3) | C7—C6—H6 | 120.1 |
C4—C5—C6 | 116.8 (3) | C5—C6—H6 | 120.1 |
C5—C6—C7 | 119.9 (3) | N1—C7—H7 | 119.1 |
N1—C7—C6 | 121.9 (2) | C6—C7—H7 | 119.1 |
| | | |
C7—N1—C2—C1 | 82.6 (3) | C3—C4—C5—O3 | 178.9 (3) |
C3—N1—C2—C1 | −92.0 (3) | C3—C4—C5—C6 | −1.4 (4) |
O2—C1—C2—N1 | 14.4 (4) | O3—C5—C6—C7 | −179.0 (3) |
O1—C1—C2—N1 | −166.9 (3) | C4—C5—C6—C7 | 1.4 (4) |
C7—N1—C3—C4 | 1.6 (5) | C3—N1—C7—C6 | −1.6 (4) |
C2—N1—C3—C4 | 176.2 (3) | C2—N1—C7—C6 | −176.3 (3) |
N1—C3—C4—C5 | −0.1 (5) | C5—C6—C7—N1 | 0.1 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 1.66 | 2.451 (3) | 163 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |
Bond distances and angles from the experimental
O═C(CH═CH)2N—CH2—CO2H structure and the geometry-optimized
O═C(CH═CH)2N—CH2—CO2H structure topBond | X-ray | Geometry optimized |
O1—C1 | 1.276 (3) | 1.350 |
O2—C1 | 1.215 (4) | 1.217 |
O3—C5 | 1.306 (3) | 1.223 |
N1—C2 | 1.473 (4) | 1.476 |
N1—C3 | 1.360 (4) | 1.416 |
N1—C7 | 1.351 (4) | 1.416 |
C1—C2 | 1.533 (4) | 1.519 |
C3—C4 | 1.356 (4) | 1.348 |
C4—C5 | 1.414 (4) | 1.472 |
C5—C6 | 1.417 (4) | 1.472 |
C6—C7 | 1.359 (4) | 1.348 |
C2—N1—C3 | 120.9 (3) | 119.0 |
C2—N1—C7 | 119.2 (2) | 118.9 |
C3—N1—C7 | 119.7 (3) | 119.1 |
O1—C1—O2 | 127.1 (3) | 116.2 |
O1—C1—C2 | 113.2 (2) | 117.6 |
O2—C1—C2 | 119.6 (2) | 126.3 |
N1—C2—C1 | 112.1 (2) | 117.0 |
N1—C3—C4 | 121.2 (3) | 121.1 |
C3—C4—C5 | 120.5 (2) | 121.4 |
O3—C5—C4 | 120.4 (2) | 122.4 |
O3—C5—C6 | 122.8 (3) | 122.4 |
C4—C5—C6 | 116.8 (3) | 115.2 |
C5—C6—C7 | 119.9 (3) | 121.4 |
N1—C7—C6 | 121.9 (2) | 121.1 |
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