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The title compound, expected to be a betaine, 4-hydroxy­pyridinio­acetate, HOC5H4N+CH2CO2 or C7H7NO3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011110/bt6460sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011110/bt6460Isup2.hkl
Contains datablock I

CCDC reference: 242328

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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
C7H7NO3F(000) = 320
Mr = 153.14Dx = 1.484 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6039 reflections
a = 4.7413 (17) Åθ = 4.5–27.3°
b = 9.595 (5) ŵ = 0.12 mm1
c = 15.069 (7) ÅT = 293 K
V = 685.5 (5) Å3Prism, yellow
Z = 40.32 × 0.25 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
945 independent reflections
Radiation source: fine-focus sealed tube857 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 65
Tmin = 0.963, Tmax = 0.977k = 1212
6046 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.19 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11.1616 (5)0.6560 (2)0.6131 (2)0.0584 (6)
O20.8553 (5)0.4920 (3)0.5715 (1)0.0645 (7)
O30.6411 (5)0.2388 (2)0.2267 (1)0.0506 (6)
N11.0913 (5)0.4646 (2)0.4077 (2)0.0432 (6)
C11.0631 (6)0.5640 (3)0.5603 (2)0.0404 (6)
C21.2403 (7)0.5460 (3)0.4760 (2)0.0519 (8)
C31.1232 (7)0.3239 (3)0.4024 (2)0.0473 (7)
C40.9744 (7)0.2474 (3)0.3430 (2)0.0458 (7)
C50.7811 (6)0.3124 (3)0.2848 (2)0.0409 (6)
C60.7482 (7)0.4585 (3)0.2935 (2)0.0432 (6)
C70.9035 (7)0.5294 (3)0.3544 (2)0.0454 (7)
H11.04010.67770.64930.070*
H2a1.28680.63710.45230.062*
H2b1.41540.49930.49100.062*
H31.24940.27940.44020.057*
H40.99970.15130.34050.055*
H60.62060.50580.25750.052*
H70.87980.62530.35950.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.058 (1)0.061 (1)0.056 (1)0.016 (1)0.014 (1)0.018 (1)
O20.063 (1)0.080 (2)0.050 (1)0.031 (1)0.013 (1)0.011 (1)
O30.063 (1)0.041 (1)0.048 (1)0.003 (1)0.008 (1)0.003 (1)
N10.047 (1)0.047 (1)0.036 (1)0.002 (1)0.004 (1)0.002 (1)
C10.044 (1)0.039 (1)0.039 (1)0.005 (1)0.001 (1)0.003 (1)
C20.055 (2)0.059 (2)0.042 (1)0.015 (2)0.004 (1)0.006 (1)
C30.051 (2)0.050 (1)0.041 (1)0.010 (1)0.001 (1)0.003 (1)
C40.055 (2)0.036 (1)0.047 (1)0.009 (1)0.003 (1)0.002 (1)
C50.051 (2)0.037 (1)0.035 (1)0.002 (1)0.005 (1)0.001 (1)
C60.051 (1)0.038 (1)0.041 (1)0.005 (1)0.001 (1)0.004 (1)
C70.058 (2)0.036 (1)0.043 (1)0.001 (1)0.007 (1)0.001 (1)
Geometric parameters (Å, º) top
O1—C11.276 (3)C5—C61.417 (4)
O2—C11.215 (4)C6—C71.359 (4)
O3—C51.306 (3)O1—H10.82
N1—C21.473 (4)C2—H2a0.97
N1—C31.360 (4)C2—H2b0.97
N1—C71.351 (4)C3—H30.93
C1—C21.533 (4)C4—H40.93
C3—C41.356 (4)C6—H60.93
C4—C51.414 (4)C7—H70.93
C2—N1—C3120.9 (3)C1—O1—H1109.5
C2—N1—C7119.2 (2)N1—C2—H2a109.2
C3—N1—C7119.7 (3)C1—C2—H2a109.2
O1—C1—O2127.1 (3)N1—C2—H2b109.2
O1—C1—C2113.2 (2)C1—C2—H2b109.2
O2—C1—C2119.6 (2)H2a—C2—H2b107.9
N1—C2—C1112.1 (2)C4—C3—H3119.4
N1—C3—C4121.2 (3)N1—C3—H3119.4
C3—C4—C5120.5 (2)C3—C4—H4119.7
O3—C5—C4120.4 (2)C5—C4—H4119.7
O3—C5—C6122.8 (3)C7—C6—H6120.1
C4—C5—C6116.8 (3)C5—C6—H6120.1
C5—C6—C7119.9 (3)N1—C7—H7119.1
N1—C7—C6121.9 (2)C6—C7—H7119.1
C7—N1—C2—C182.6 (3)C3—C4—C5—O3178.9 (3)
C3—N1—C2—C192.0 (3)C3—C4—C5—C61.4 (4)
O2—C1—C2—N114.4 (4)O3—C5—C6—C7179.0 (3)
O1—C1—C2—N1166.9 (3)C4—C5—C6—C71.4 (4)
C7—N1—C3—C41.6 (5)C3—N1—C7—C61.6 (4)
C2—N1—C3—C4176.2 (3)C2—N1—C7—C6176.3 (3)
N1—C3—C4—C50.1 (5)C5—C6—C7—N10.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.821.662.451 (3)163
Symmetry code: (i) x+3/2, y+1, z+1/2.
Bond distances and angles from the experimental OC(CHCH)2N—CH2—CO2H structure and the geometry-optimized OC(CHCH)2N—CH2—CO2H structure top
BondX-rayGeometry optimized
O1—C11.276 (3)1.350
O2—C11.215 (4)1.217
O3—C51.306 (3)1.223
N1—C21.473 (4)1.476
N1—C31.360 (4)1.416
N1—C71.351 (4)1.416
C1—C21.533 (4)1.519
C3—C41.356 (4)1.348
C4—C51.414 (4)1.472
C5—C61.417 (4)1.472
C6—C71.359 (4)1.348
C2—N1—C3120.9 (3)119.0
C2—N1—C7119.2 (2)118.9
C3—N1—C7119.7 (3)119.1
O1—C1—O2127.1 (3)116.2
O1—C1—C2113.2 (2)117.6
O2—C1—C2119.6 (2)126.3
N1—C2—C1112.1 (2)117.0
N1—C3—C4121.2 (3)121.1
C3—C4—C5120.5 (2)121.4
O3—C5—C4120.4 (2)122.4
O3—C5—C6122.8 (3)122.4
C4—C5—C6116.8 (3)115.2
C5—C6—C7119.9 (3)121.4
N1—C7—C6121.9 (2)121.1
 

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