The title compound, C
6H
5NO
2, a tautomer of 2-hydroxynicotinic acid, adopts a planar conformation. An intramolecular O—H
O hydrogen bond of 2.504 (2) Å is found. The compound forms one-dimensional hydrogen-bonded chains along the [
01] direction
via an intermolecular N—H
O hydrogen bond of 2.810 (2) Å.
Supporting information
CCDC reference: 630044
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.002 Å
- R factor = 0.045
- wR factor = 0.130
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 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
0 ALERT type 3 Indicator that the structure quality may be low
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0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97 and local procedures.
2-Oxo-1,2-dihydropyridine-3-carboxylic acid
top
Crystal data top
C6H5NO3 | Dx = 1.621 Mg m−3 |
Mr = 139.11 | Melting point = 532–535 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 3.640 (1) Å | Cell parameters from 1370 reflections |
b = 11.584 (3) Å | θ = 1.0–27.5° |
c = 13.565 (3) Å | µ = 0.13 mm−1 |
β = 94.64 (1)° | T = 90 K |
V = 570.1 (2) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.20 × 0.15 mm |
F(000) = 288 | |
Data collection top
Nonius KappaCCD diffractometer | 1307 independent reflections |
Radiation source: fine-focus sealed tube | 971 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 2.3° |
ω scans at fixed χ = 55° | h = −4→4 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −15→15 |
Tmin = 0.961, Tmax = 0.980 | l = −17→17 |
2539 measured reflections | |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0761P)2 + 0.1679P] where P = (Fo2 + 2Fc2)/3 |
1307 reflections | (Δ/σ)max < 0.001 |
92 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.28 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 | |
C2 | 0.5633 (4) | 0.25484 (14) | 0.33937 (12) | 0.0161 (4) | |
C3 | 0.4124 (4) | 0.18122 (14) | 0.41096 (12) | 0.0149 (4) | |
C4 | 0.3141 (4) | 0.06996 (14) | 0.38714 (12) | 0.0160 (4) | |
H4 | 0.2153 | 0.0222 | 0.4354 | 0.019* | |
C5 | 0.3568 (4) | 0.02535 (15) | 0.29270 (12) | 0.0185 (4) | |
H5 | 0.2937 | −0.0524 | 0.2768 | 0.022* | |
C6 | 0.4913 (4) | 0.09673 (15) | 0.22447 (12) | 0.0179 (4) | |
H6 | 0.5201 | 0.0685 | 0.1598 | 0.021* | |
C7 | 0.3601 (4) | 0.22936 (15) | 0.51047 (12) | 0.0175 (4) | |
N1 | 0.5846 (4) | 0.20702 (13) | 0.24719 (10) | 0.0174 (3) | |
H1 | 0.6636 | 0.2508 | 0.2003 | 0.021* | |
O8 | 0.4619 (4) | 0.33727 (10) | 0.52644 (9) | 0.0218 (3) | |
H8 | 0.5445 | 0.3644 | 0.4752 | 0.033* | |
O9 | 0.2246 (3) | 0.17228 (10) | 0.57449 (8) | 0.0216 (3) | |
O10 | 0.6713 (3) | 0.35672 (10) | 0.35588 (9) | 0.0209 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C2 | 0.0139 (8) | 0.0182 (9) | 0.0161 (8) | 0.0024 (6) | 0.0007 (6) | 0.0022 (7) |
C3 | 0.0129 (8) | 0.0182 (8) | 0.0136 (8) | 0.0011 (6) | 0.0009 (6) | 0.0015 (6) |
C4 | 0.0126 (7) | 0.0188 (9) | 0.0167 (8) | 0.0014 (6) | 0.0018 (6) | 0.0031 (6) |
C5 | 0.0177 (8) | 0.0174 (9) | 0.0202 (9) | 0.0015 (7) | 0.0003 (7) | −0.0016 (7) |
C6 | 0.0172 (8) | 0.0213 (9) | 0.0149 (8) | 0.0040 (7) | 0.0000 (6) | −0.0025 (7) |
C7 | 0.0165 (8) | 0.0191 (9) | 0.0168 (8) | 0.0025 (6) | 0.0000 (6) | 0.0004 (7) |
N1 | 0.0181 (7) | 0.0207 (8) | 0.0136 (7) | 0.0002 (6) | 0.0034 (5) | 0.0030 (5) |
O8 | 0.0286 (7) | 0.0202 (7) | 0.0168 (6) | −0.0013 (5) | 0.0038 (5) | −0.0020 (5) |
O9 | 0.0269 (7) | 0.0232 (7) | 0.0154 (6) | 0.0014 (5) | 0.0066 (5) | 0.0014 (5) |
O10 | 0.0242 (7) | 0.0170 (7) | 0.0217 (6) | −0.0017 (5) | 0.0031 (5) | 0.0018 (5) |
Geometric parameters (Å, º) top
C2—O10 | 1.258 (2) | C5—H5 | 0.9500 |
C2—N1 | 1.376 (2) | C6—N1 | 1.351 (2) |
C2—C3 | 1.435 (2) | C6—H6 | 0.9500 |
C3—C4 | 1.369 (2) | C7—O9 | 1.2264 (19) |
C3—C7 | 1.487 (2) | C7—O8 | 1.317 (2) |
C4—C5 | 1.402 (2) | N1—H1 | 0.8800 |
C4—H4 | 0.9500 | O8—H8 | 0.8400 |
C5—C6 | 1.362 (2) | | |
| | | |
O10—C2—N1 | 119.98 (14) | C4—C5—H5 | 121.0 |
O10—C2—C3 | 124.63 (14) | N1—C6—C5 | 121.11 (15) |
N1—C2—C3 | 115.40 (15) | N1—C6—H6 | 119.4 |
C4—C3—C2 | 120.45 (15) | C5—C6—H6 | 119.4 |
C4—C3—C7 | 121.13 (15) | O9—C7—O8 | 121.29 (15) |
C2—C3—C7 | 118.41 (15) | O9—C7—C3 | 121.94 (15) |
C3—C4—C5 | 121.11 (15) | O8—C7—C3 | 116.77 (14) |
C3—C4—H4 | 119.4 | C6—N1—C2 | 123.82 (14) |
C5—C4—H4 | 119.4 | C6—N1—H1 | 118.1 |
C6—C5—C4 | 118.03 (16) | C2—N1—H1 | 118.1 |
C6—C5—H5 | 121.0 | C7—O8—H8 | 109.5 |
| | | |
O10—C2—C3—C4 | −177.69 (15) | C4—C3—C7—O9 | −0.7 (3) |
N1—C2—C3—C4 | 2.5 (2) | C2—C3—C7—O9 | 178.23 (15) |
O10—C2—C3—C7 | 3.4 (2) | C4—C3—C7—O8 | −179.82 (15) |
N1—C2—C3—C7 | −176.41 (14) | C2—C3—C7—O8 | −0.9 (2) |
C2—C3—C4—C5 | −0.2 (2) | C5—C6—N1—C2 | 2.0 (2) |
C7—C3—C4—C5 | 178.73 (15) | O10—C2—N1—C6 | 176.74 (15) |
C3—C4—C5—C6 | −1.5 (2) | C3—C2—N1—C6 | −3.5 (2) |
C4—C5—C6—N1 | 0.6 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O9i | 0.88 | 1.95 | 2.8100 (18) | 164 |
O8—H8···O10 | 0.84 | 1.72 | 2.5040 (17) | 154 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |