Acta Cryst. (2007). E63, o2784 [ doi:10.1107/S1600536807020958 ]
The title compound, C6H5NO3, commonly known as 6-hydroxynicotinic acid, is found to be a tautomer of it. Four molecules, all adopting a planar conformation, are found in the asymmetric unit. The compound forms hydrogen-bonded sheets parallel to the [001] direction via intermolecular N-H
O and O-HO hydrogen bonds. Each sheet consists of interconnected dimers created by R22(8) N-HO hydrogen-bonded motifs and infinite chains formed by C(7) hydrogen-bonded motifs. Alternatively, these sheets can be viewed as infinitely fused 32-membered hydrogen-bonded rings.
6-Hydroxynicotinic acid was purchased from Alfa Aesar. Crystals of the title compound were grown from dimethylsulfoxide solution by slow evaporation.
Data collection: COLLECT (Nonius, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1995); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 1995) and local procedures.
![[Figure 1]](./fl2129fig1thm.gif)
| Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms). |
![[Figure 2]](./fl2129fig2thm.gif)
| Fig. 2. A packing diagram of (I) along a axis. |
| C6H5NO3 | Z = 8 |
| Mr = 139.11 | F(000) = 576 |
| Triclinic, P1 | Dx = 1.580 Mg m−3 |
| a = 6.8130 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
| b = 11.1340 (3) Å | Cell parameters from 5285 reflections |
| c = 16.2780 (4) Å | θ = 1.0–27.5° |
| α = 82.5570 (9)° | µ = 0.13 mm−1 |
| β = 78.106 (1)° | T = 90 K |
| γ = 76.251 (1)° | Irregular block, colourless |
| V = 1169.43 (5) Å3 | 0.30 × 0.20 × 0.10 mm |
| Nonius KappaCCD diffractometer | 5330 independent reflections |
| Radiation source: fine-focus sealed tube | 3206 reflections with I > 2σ(I) |
| graphite | Rint = 0.042 |
| Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 1.3° |
| ω scans at fixed χ = 55° | h = −8→8 |
| Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −14→14 |
| Tmin = 0.962, Tmax = 0.987 | l = −21→21 |
| 10567 measured reflections |
| 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.156 | H-atom parameters constrained |
| S = 1.00 | w = 1/[σ2(Fo2) + (0.0889P)2] where P = (Fo2 + 2Fc2)/3 |
| 5330 reflections | (Δ/σ)max < 0.001 |
| 365 parameters | Δρmax = 0.44 e Å−3 |
| 0 restraints | Δρmin = −0.33 e Å−3 |
| C6H5NO3 | γ = 76.251 (1)° |
| Mr = 139.11 | V = 1169.43 (5) Å3 |
| Triclinic, P1 | Z = 8 |
| a = 6.8130 (1) Å | Mo Kα radiation |
| b = 11.1340 (3) Å | µ = 0.13 mm−1 |
| c = 16.2780 (4) Å | T = 90 K |
| α = 82.5570 (9)° | 0.30 × 0.20 × 0.10 mm |
| β = 78.106 (1)° |
| Nonius KappaCCD diffractometer | 5330 independent reflections |
| Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 3206 reflections with I > 2σ(I) |
| Tmin = 0.962, Tmax = 0.987 | Rint = 0.042 |
| 10567 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
| wR(F2) = 0.156 | Δρmax = 0.44 e Å−3 |
| S = 1.00 | Δρmin = −0.33 e Å−3 |
| 5330 reflections | Absolute structure: ? |
| 365 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| O1A | −0.2663 (2) | 0.02267 (12) | 0.12836 (9) | 0.0246 (4) | |
| N1A | 0.0776 (2) | −0.31841 (14) | 0.28713 (10) | 0.0172 (4) | |
| H1A | 0.1450 | −0.3964 | 0.2874 | 0.021* | |
| O2A | −0.0747 (2) | −0.14740 (12) | 0.06663 (9) | 0.0228 (4) | |
| H2A | −0.1243 | −0.1118 | 0.0244 | 0.034* | |
| C2A | 0.0217 (3) | −0.26190 (18) | 0.21448 (12) | 0.0170 (4) | |
| H2A1 | 0.0576 | −0.3062 | 0.1655 | 0.020* | |
| O3A | 0.0935 (2) | −0.32412 (12) | 0.42539 (8) | 0.0208 (3) | |
| C3A | −0.0858 (3) | −0.14206 (18) | 0.21055 (12) | 0.0167 (4) | |
| C4A | −0.1339 (3) | −0.07843 (18) | 0.28476 (13) | 0.0190 (5) | |
| H4A | −0.2095 | 0.0051 | 0.2837 | 0.023* | |
| C5A | −0.0734 (3) | −0.13532 (18) | 0.35741 (13) | 0.0202 (5) | |
| H5A | −0.1038 | −0.0908 | 0.4061 | 0.024* | |
| C6A | 0.0358 (3) | −0.26180 (18) | 0.36048 (12) | 0.0178 (5) | |
| C7A | −0.1531 (3) | −0.07933 (18) | 0.13204 (12) | 0.0184 (5) | |
| O1B | 0.3848 (2) | −0.08869 (13) | 0.40114 (9) | 0.0266 (4) | |
| N1B | 0.6711 (2) | −0.43693 (14) | 0.57089 (10) | 0.0178 (4) | |
| H1B | 0.7396 | −0.5146 | 0.5717 | 0.021* | |
| O2B | 0.5393 (2) | −0.27162 (12) | 0.34799 (9) | 0.0223 (3) | |
| H2B | 0.5115 | −0.2324 | 0.3027 | 0.033* | |
| C2B | 0.6289 (3) | −0.37921 (18) | 0.49640 (12) | 0.0177 (5) | |
| H2B1 | 0.6717 | −0.4232 | 0.4473 | 0.021* | |
| O3B | 0.6605 (2) | −0.44604 (12) | 0.71141 (9) | 0.0225 (4) | |
| C3B | 0.5257 (3) | −0.25881 (18) | 0.49095 (12) | 0.0173 (4) | |
| C4B | 0.4673 (3) | −0.19573 (19) | 0.56541 (13) | 0.0190 (5) | |
| H4B | 0.3986 | −0.1108 | 0.5629 | 0.023* | |
| C5B | 0.5084 (3) | −0.25521 (17) | 0.64043 (13) | 0.0179 (4) | |
| H5B | 0.4665 | −0.2120 | 0.6899 | 0.021* | |
| C6B | 0.6141 (3) | −0.38239 (19) | 0.64511 (13) | 0.0184 (5) | |
| C7B | 0.4748 (3) | −0.19628 (18) | 0.40984 (13) | 0.0194 (5) | |
| N1C | 0.4331 (2) | −0.18372 (15) | 0.06937 (10) | 0.0177 (4) | |
| H1C | 0.3515 | −0.1095 | 0.0698 | 0.021* | |
| O1C | 0.7973 (2) | −0.51108 (12) | −0.09714 (9) | 0.0256 (4) | |
| O2C | 0.5683 (2) | −0.35163 (12) | −0.14625 (9) | 0.0249 (4) | |
| H2C | 0.6060 | −0.3885 | −0.1906 | 0.037* | |
| C2C | 0.4836 (3) | −0.23954 (18) | −0.00307 (12) | 0.0169 (4) | |
| H2C1 | 0.4297 | −0.1989 | −0.0512 | 0.020* | |
| O3C | 0.4444 (2) | −0.17246 (12) | 0.20599 (8) | 0.0204 (3) | |
| C3C | 0.6111 (3) | −0.35363 (17) | −0.00764 (12) | 0.0167 (4) | |
| C4C | 0.6874 (3) | −0.41203 (18) | 0.06576 (13) | 0.0198 (5) | |
| H4C | 0.7786 | −0.4912 | 0.0638 | 0.024* | |
| C5C | 0.6310 (3) | −0.35561 (17) | 0.13909 (13) | 0.0189 (5) | |
| H5C | 0.6791 | −0.3970 | 0.1883 | 0.023* | |
| C6C | 0.5007 (3) | −0.23520 (18) | 0.14232 (12) | 0.0165 (4) | |
| C7C | 0.6702 (3) | −0.41509 (18) | −0.08724 (13) | 0.0186 (5) | |
| O1D | −0.1487 (2) | 0.40702 (12) | 0.36990 (9) | 0.0247 (4) | |
| N1D | 0.2167 (2) | 0.07385 (15) | 0.20876 (10) | 0.0185 (4) | |
| H1D | 0.3099 | 0.0039 | 0.2075 | 0.022* | |
| O2D | 0.0118 (2) | 0.22789 (12) | 0.43099 (9) | 0.0243 (4) | |
| H2D | −0.0248 | 0.2668 | 0.4744 | 0.036* | |
| C2D | 0.1569 (3) | 0.12889 (17) | 0.28185 (12) | 0.0174 (5) | |
| H2D1 | 0.2118 | 0.0904 | 0.3302 | 0.021* | |
| O3D | 0.2057 (2) | 0.05834 (12) | 0.07258 (8) | 0.0202 (3) | |
| C3D | 0.0185 (3) | 0.23908 (18) | 0.28634 (12) | 0.0170 (4) | |
| C4D | −0.0627 (3) | 0.29300 (18) | 0.21338 (13) | 0.0202 (5) | |
| H4D | −0.1589 | 0.3704 | 0.2152 | 0.024* | |
| C5D | −0.0047 (3) | 0.23539 (18) | 0.14063 (13) | 0.0197 (5) | |
| H5D | −0.0617 | 0.2721 | 0.0924 | 0.024* | |
| C6D | 0.1415 (3) | 0.12008 (18) | 0.13673 (12) | 0.0170 (4) | |
| C7D | −0.0489 (3) | 0.30178 (18) | 0.36576 (13) | 0.0182 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1A | 0.0280 (8) | 0.0195 (8) | 0.0241 (9) | 0.0008 (6) | −0.0087 (7) | 0.0007 (7) |
| N1A | 0.0215 (9) | 0.0129 (9) | 0.0154 (10) | 0.0005 (7) | −0.0047 (7) | −0.0013 (7) |
| O2A | 0.0314 (9) | 0.0193 (8) | 0.0170 (8) | 0.0006 (6) | −0.0106 (7) | −0.0011 (6) |
| C2A | 0.0202 (11) | 0.0195 (11) | 0.0112 (11) | −0.0026 (9) | −0.0043 (8) | −0.0021 (8) |
| O3A | 0.0283 (8) | 0.0190 (8) | 0.0135 (8) | 0.0012 (6) | −0.0068 (6) | −0.0025 (6) |
| C3A | 0.0181 (10) | 0.0159 (10) | 0.0161 (11) | −0.0040 (8) | −0.0040 (8) | 0.0004 (8) |
| C4A | 0.0197 (11) | 0.0140 (10) | 0.0223 (12) | −0.0004 (8) | −0.0042 (9) | −0.0036 (9) |
| C5A | 0.0237 (11) | 0.0180 (11) | 0.0185 (12) | −0.0021 (9) | −0.0028 (9) | −0.0058 (9) |
| C6A | 0.0184 (10) | 0.0215 (11) | 0.0140 (11) | −0.0038 (8) | −0.0045 (9) | −0.0015 (9) |
| C7A | 0.0180 (11) | 0.0201 (12) | 0.0189 (12) | −0.0058 (9) | −0.0047 (9) | −0.0030 (9) |
| O1B | 0.0340 (9) | 0.0199 (8) | 0.0220 (9) | 0.0033 (7) | −0.0083 (7) | 0.0003 (6) |
| N1B | 0.0218 (9) | 0.0135 (9) | 0.0168 (10) | 0.0006 (7) | −0.0053 (7) | −0.0024 (7) |
| O2B | 0.0308 (8) | 0.0209 (8) | 0.0142 (8) | −0.0014 (7) | −0.0076 (7) | −0.0003 (6) |
| C2B | 0.0214 (11) | 0.0187 (11) | 0.0134 (11) | −0.0033 (9) | −0.0052 (9) | −0.0016 (8) |
| O3B | 0.0296 (8) | 0.0199 (8) | 0.0159 (8) | 0.0021 (6) | −0.0081 (6) | −0.0017 (6) |
| C3B | 0.0181 (10) | 0.0174 (11) | 0.0164 (11) | −0.0036 (8) | −0.0049 (9) | 0.0005 (8) |
| C4B | 0.0190 (11) | 0.0154 (10) | 0.0218 (12) | −0.0008 (8) | −0.0053 (9) | −0.0017 (9) |
| C5B | 0.0193 (11) | 0.0178 (11) | 0.0153 (11) | −0.0004 (8) | −0.0019 (8) | −0.0056 (8) |
| C6B | 0.0184 (11) | 0.0238 (11) | 0.0133 (11) | −0.0042 (9) | −0.0032 (9) | −0.0039 (9) |
| C7B | 0.0203 (11) | 0.0188 (12) | 0.0187 (12) | −0.0030 (9) | −0.0045 (9) | −0.0005 (9) |
| N1C | 0.0211 (9) | 0.0155 (9) | 0.0145 (9) | 0.0016 (7) | −0.0055 (7) | −0.0011 (7) |
| O1C | 0.0300 (9) | 0.0208 (8) | 0.0240 (9) | 0.0026 (7) | −0.0065 (7) | −0.0073 (7) |
| O2C | 0.0326 (9) | 0.0223 (8) | 0.0174 (8) | 0.0035 (7) | −0.0086 (7) | −0.0045 (6) |
| C2C | 0.0206 (11) | 0.0182 (11) | 0.0119 (11) | −0.0038 (8) | −0.0043 (8) | −0.0003 (8) |
| O3C | 0.0259 (8) | 0.0187 (8) | 0.0154 (8) | −0.0010 (6) | −0.0044 (6) | −0.0037 (6) |
| C3C | 0.0193 (11) | 0.0166 (11) | 0.0140 (11) | −0.0034 (8) | −0.0026 (8) | −0.0026 (8) |
| C4C | 0.0215 (11) | 0.0130 (10) | 0.0236 (12) | 0.0003 (8) | −0.0057 (9) | −0.0015 (9) |
| C5C | 0.0238 (11) | 0.0143 (11) | 0.0178 (11) | 0.0006 (8) | −0.0092 (9) | 0.0014 (8) |
| C6C | 0.0200 (11) | 0.0188 (11) | 0.0115 (11) | −0.0063 (8) | −0.0031 (8) | −0.0001 (9) |
| C7C | 0.0217 (11) | 0.0169 (11) | 0.0181 (11) | −0.0049 (9) | −0.0042 (9) | −0.0022 (9) |
| O1D | 0.0304 (8) | 0.0187 (8) | 0.0230 (9) | 0.0010 (7) | −0.0040 (7) | −0.0072 (6) |
| N1D | 0.0226 (9) | 0.0160 (9) | 0.0152 (9) | 0.0015 (7) | −0.0049 (7) | −0.0033 (7) |
| O2D | 0.0311 (9) | 0.0237 (8) | 0.0161 (8) | 0.0019 (7) | −0.0060 (7) | −0.0065 (6) |
| C2D | 0.0236 (11) | 0.0163 (11) | 0.0133 (11) | −0.0050 (9) | −0.0047 (9) | −0.0011 (8) |
| O3D | 0.0270 (8) | 0.0171 (8) | 0.0156 (8) | −0.0006 (6) | −0.0052 (6) | −0.0044 (6) |
| C3D | 0.0190 (11) | 0.0166 (11) | 0.0157 (11) | −0.0042 (8) | −0.0020 (9) | −0.0039 (8) |
| C4D | 0.0208 (11) | 0.0158 (11) | 0.0226 (12) | 0.0003 (8) | −0.0061 (9) | −0.0017 (9) |
| C5D | 0.0236 (11) | 0.0184 (11) | 0.0170 (11) | −0.0035 (9) | −0.0073 (9) | 0.0027 (9) |
| C6D | 0.0224 (11) | 0.0154 (10) | 0.0146 (11) | −0.0059 (8) | −0.0046 (9) | −0.0008 (8) |
| C7D | 0.0177 (10) | 0.0183 (11) | 0.0190 (12) | −0.0025 (9) | −0.0042 (9) | −0.0036 (9) |
| O1A—C7A | 1.214 (2) | N1C—C2C | 1.348 (2) |
| N1A—C2A | 1.348 (2) | N1C—C6C | 1.369 (2) |
| N1A—C6A | 1.369 (2) | N1C—H1C | 0.8800 |
| N1A—H1A | 0.8800 | O1C—C7C | 1.211 (2) |
| O2A—C7A | 1.333 (2) | O2C—C7C | 1.330 (2) |
| O2A—H2A | 0.8400 | O2C—H2C | 0.8400 |
| C2A—C3A | 1.361 (3) | C2C—C3C | 1.359 (3) |
| C2A—H2A1 | 0.9500 | C2C—H2C1 | 0.9500 |
| O3A—C6A | 1.267 (2) | O3C—C6C | 1.267 (2) |
| C3A—C4A | 1.420 (3) | C3C—C4C | 1.419 (3) |
| C3A—C7A | 1.480 (3) | C3C—C7C | 1.481 (3) |
| C4A—C5A | 1.361 (3) | C4C—C5C | 1.363 (3) |
| C4A—H4A | 0.9500 | C4C—H4C | 0.9500 |
| C5A—C6A | 1.428 (3) | C5C—C6C | 1.422 (3) |
| C5A—H5A | 0.9500 | C5C—H5C | 0.9500 |
| O1B—C7B | 1.214 (2) | O1D—C7D | 1.209 (2) |
| N1B—C2B | 1.349 (2) | N1D—C2D | 1.352 (2) |
| N1B—C6B | 1.365 (2) | N1D—C6D | 1.367 (2) |
| N1B—H1B | 0.8800 | N1D—H1D | 0.8800 |
| O2B—C7B | 1.331 (2) | O2D—C7D | 1.330 (2) |
| O2B—H2B | 0.8400 | O2D—H2D | 0.8400 |
| C2B—C3B | 1.359 (3) | C2D—C3D | 1.358 (3) |
| C2B—H2B1 | 0.9500 | C2D—H2D1 | 0.9500 |
| O3B—C6B | 1.266 (2) | O3D—C6D | 1.269 (2) |
| C3B—C4B | 1.418 (3) | C3D—C4D | 1.416 (3) |
| C3B—C7B | 1.478 (3) | C3D—C7D | 1.485 (3) |
| C4B—C5B | 1.361 (3) | C4D—C5D | 1.361 (3) |
| C4B—H4B | 0.9500 | C4D—H4D | 0.9500 |
| C5B—C6B | 1.428 (3) | C5D—C6D | 1.425 (3) |
| C5B—H5B | 0.9500 | C5D—H5D | 0.9500 |
| C2A—N1A—C6A | 123.93 (17) | C2C—N1C—C6C | 124.17 (17) |
| C2A—N1A—H1A | 118.0 | C2C—N1C—H1C | 117.9 |
| C6A—N1A—H1A | 118.0 | C6C—N1C—H1C | 117.9 |
| C7A—O2A—H2A | 109.5 | C7C—O2C—H2C | 109.5 |
| N1A—C2A—C3A | 120.71 (18) | N1C—C2C—C3C | 120.42 (18) |
| N1A—C2A—H2A1 | 119.6 | N1C—C2C—H2C1 | 119.8 |
| C3A—C2A—H2A1 | 119.6 | C3C—C2C—H2C1 | 119.8 |
| C2A—C3A—C4A | 117.94 (18) | C2C—C3C—C4C | 118.25 (18) |
| C2A—C3A—C7A | 121.57 (18) | C2C—C3C—C7C | 120.91 (18) |
| C4A—C3A—C7A | 120.48 (17) | C4C—C3C—C7C | 120.84 (17) |
| C5A—C4A—C3A | 121.00 (18) | C5C—C4C—C3C | 120.62 (18) |
| C5A—C4A—H4A | 119.5 | C5C—C4C—H4C | 119.7 |
| C3A—C4A—H4A | 119.5 | C3C—C4C—H4C | 119.7 |
| C4A—C5A—C6A | 120.07 (18) | C4C—C5C—C6C | 120.38 (18) |
| C4A—C5A—H5A | 120.0 | C4C—C5C—H5C | 119.8 |
| C6A—C5A—H5A | 120.0 | C6C—C5C—H5C | 119.8 |
| O3A—C6A—N1A | 118.68 (17) | O3C—C6C—N1C | 118.10 (17) |
| O3A—C6A—C5A | 124.99 (18) | O3C—C6C—C5C | 125.77 (18) |
| N1A—C6A—C5A | 116.33 (18) | N1C—C6C—C5C | 116.12 (17) |
| O1A—C7A—O2A | 124.41 (18) | O1C—C7C—O2C | 124.41 (18) |
| O1A—C7A—C3A | 123.34 (19) | O1C—C7C—C3C | 123.70 (18) |
| O2A—C7A—C3A | 112.25 (16) | O2C—C7C—C3C | 111.89 (16) |
| C2B—N1B—C6B | 124.13 (17) | C2D—N1D—C6D | 124.12 (16) |
| C2B—N1B—H1B | 117.9 | C2D—N1D—H1D | 117.9 |
| C6B—N1B—H1B | 117.9 | C6D—N1D—H1D | 117.9 |
| C7B—O2B—H2B | 109.5 | C7D—O2D—H2D | 109.5 |
| N1B—C2B—C3B | 120.68 (18) | N1D—C2D—C3D | 120.23 (18) |
| N1B—C2B—H2B1 | 119.7 | N1D—C2D—H2D1 | 119.9 |
| C3B—C2B—H2B1 | 119.7 | C3D—C2D—H2D1 | 119.9 |
| C2B—C3B—C4B | 117.98 (18) | C2D—C3D—C4D | 118.41 (18) |
| C2B—C3B—C7B | 120.79 (18) | C2D—C3D—C7D | 121.28 (18) |
| C4B—C3B—C7B | 121.23 (17) | C4D—C3D—C7D | 120.30 (17) |
| C5B—C4B—C3B | 120.88 (18) | C5D—C4D—C3D | 120.83 (18) |
| C5B—C4B—H4B | 119.6 | C5D—C4D—H4D | 119.6 |
| C3B—C4B—H4B | 119.6 | C3D—C4D—H4D | 119.6 |
| C4B—C5B—C6B | 120.28 (18) | C4D—C5D—C6D | 120.13 (19) |
| C4B—C5B—H5B | 119.9 | C4D—C5D—H5D | 119.9 |
| C6B—C5B—H5B | 119.9 | C6D—C5D—H5D | 119.9 |
| O3B—C6B—N1B | 118.63 (18) | O3D—C6D—N1D | 118.35 (17) |
| O3B—C6B—C5B | 125.34 (18) | O3D—C6D—C5D | 125.40 (18) |
| N1B—C6B—C5B | 116.02 (18) | N1D—C6D—C5D | 116.25 (17) |
| O1B—C7B—O2B | 124.30 (19) | O1D—C7D—O2D | 124.66 (18) |
| O1B—C7B—C3B | 123.60 (19) | O1D—C7D—C3D | 123.49 (18) |
| O2B—C7B—C3B | 112.10 (16) | O2D—C7D—C3D | 111.84 (16) |
| C6A—N1A—C2A—C3A | −1.1 (3) | C6C—N1C—C2C—C3C | −0.8 (3) |
| N1A—C2A—C3A—C4A | 0.9 (3) | N1C—C2C—C3C—C4C | 0.5 (3) |
| N1A—C2A—C3A—C7A | −178.44 (17) | N1C—C2C—C3C—C7C | −179.07 (17) |
| C2A—C3A—C4A—C5A | 0.4 (3) | C2C—C3C—C4C—C5C | 1.0 (3) |
| C7A—C3A—C4A—C5A | 179.77 (17) | C7C—C3C—C4C—C5C | −179.38 (17) |
| C3A—C4A—C5A—C6A | −1.6 (3) | C3C—C4C—C5C—C6C | −2.3 (3) |
| C2A—N1A—C6A—O3A | 179.19 (17) | C2C—N1C—C6C—O3C | 179.05 (16) |
| C2A—N1A—C6A—C5A | −0.1 (3) | C2C—N1C—C6C—C5C | −0.4 (3) |
| C4A—C5A—C6A—O3A | −177.83 (19) | C4C—C5C—C6C—O3C | −177.47 (19) |
| C4A—C5A—C6A—N1A | 1.4 (3) | C4C—C5C—C6C—N1C | 2.0 (3) |
| C2A—C3A—C7A—O1A | 172.31 (19) | C2C—C3C—C7C—O1C | 173.01 (19) |
| C4A—C3A—C7A—O1A | −7.0 (3) | C4C—C3C—C7C—O1C | −6.6 (3) |
| C2A—C3A—C7A—O2A | −7.9 (3) | C2C—C3C—C7C—O2C | −6.5 (3) |
| C4A—C3A—C7A—O2A | 172.71 (16) | C4C—C3C—C7C—O2C | 173.96 (17) |
| C6B—N1B—C2B—C3B | 0.8 (3) | C6D—N1D—C2D—C3D | −2.2 (3) |
| N1B—C2B—C3B—C4B | 1.0 (3) | N1D—C2D—C3D—C4D | 1.0 (3) |
| N1B—C2B—C3B—C7B | −178.48 (17) | N1D—C2D—C3D—C7D | −179.68 (17) |
| C2B—C3B—C4B—C5B | −1.8 (3) | C2D—C3D—C4D—C5D | 0.5 (3) |
| C7B—C3B—C4B—C5B | 177.66 (17) | C7D—C3D—C4D—C5D | −178.90 (17) |
| C3B—C4B—C5B—C6B | 0.9 (3) | C3D—C4D—C5D—C6D | −0.8 (3) |
| C2B—N1B—C6B—O3B | 179.36 (17) | C2D—N1D—C6D—O3D | −178.20 (16) |
| C2B—N1B—C6B—C5B | −1.8 (3) | C2D—N1D—C6D—C5D | 1.8 (3) |
| C4B—C5B—C6B—O3B | 179.67 (19) | C4D—C5D—C6D—O3D | 179.71 (18) |
| C4B—C5B—C6B—N1B | 0.9 (3) | C4D—C5D—C6D—N1D | −0.3 (3) |
| C2B—C3B—C7B—O1B | −179.27 (19) | C2D—C3D—C7D—O1D | 169.38 (19) |
| C4B—C3B—C7B—O1B | 1.3 (3) | C4D—C3D—C7D—O1D | −11.3 (3) |
| C2B—C3B—C7B—O2B | 0.7 (3) | C2D—C3D—C7D—O2D | −11.3 (3) |
| C4B—C3B—C7B—O2B | −178.76 (17) | C4D—C3D—C7D—O2D | 168.02 (17) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2A—H2A···O3Di | 0.84 | 1.76 | 2.5971 (18) | 171 |
| N1D—H1D···O3C | 0.88 | 1.96 | 2.813 (2) | 163 |
| O2D—H2D···O3Aii | 0.84 | 1.76 | 2.5925 (19) | 171 |
| O2B—H2B···O3C | 0.84 | 1.74 | 2.5681 (19) | 171 |
| N1B—H1B···O3Aiii | 0.88 | 1.88 | 2.761 (2) | 175 |
| N1A—H1A···O3Biii | 0.88 | 1.93 | 2.800 (2) | 169 |
| O2C—H2C···O3Biv | 0.84 | 1.73 | 2.5661 (19) | 172 |
| N1C—H1C···O3D | 0.88 | 1.90 | 2.772 (2) | 173 |
| Symmetry codes: (i) −x, −y, −z; (ii) −x, −y, −z+1; (iii) −x+1, −y−1, −z+1; (iv) x, y, z−1. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2A—H2A···O3Di | 0.84 | 1.76 | 2.5971 (18) | 171 |
| N1D—H1D···O3C | 0.88 | 1.96 | 2.813 (2) | 163 |
| O2D—H2D···O3Aii | 0.84 | 1.76 | 2.5925 (19) | 171 |
| O2B—H2B···O3C | 0.84 | 1.74 | 2.5681 (19) | 171 |
| N1B—H1B···O3Aiii | 0.88 | 1.88 | 2.761 (2) | 175 |
| N1A—H1A···O3Biii | 0.88 | 1.93 | 2.800 (2) | 169 |
| O2C—H2C···O3Biv | 0.84 | 1.73 | 2.5661 (19) | 172 |
| N1C—H1C···O3D | 0.88 | 1.90 | 2.772 (2) | 173 |
| Symmetry codes: (i) −x, −y, −z; (ii) −x, −y, −z+1; (iii) −x+1, −y−1, −z+1; (iv) x, y, z−1. |
The authors appreciate Dr Sean Parkin for providing support and laboratory facilities. The authors also thank NSF for financial support (DMR-0449633).
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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
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The title compound (I), along with 2-hydroxynicotinic acid (II), are useful intermediates for the synthesis of pharmaceuticals and agrochemicals. Microbial production of both compounds from just nicotinic acid has been investigated by different groups. Bacteria which can regio-selectively hydrolyze nicotinic acid at positions 2 and 6 have been isolated successfully (Tinschert et al., 1997). The spectral characteristics of II, and the factors affecting it, have been studied by Dogra (2005). The presence of II was found to be insignificant in various types of solvents because tautomerization led to 1,2-dihydro-2-oxo-3-pyridinecarboxylic acid, the tautomer of II. We reported the first crystal structure of II previously (Long et al., 2006). The solid state structure of II turned out to be 1,2-dihydro-2-oxo-3-pyridinecarboxylic acid. That was in agreement with Dogra's findings. In addition, the compound formed one-dimensional hydrogen-bonded chains along the [-1 0 1] direction via intermolecular N—H···O hydrogen bonds. Intramolecular R11(6) O—H···O hydrogen bonds were also found (Etter, 1990).
To systematically study the solid state structures of hydroxynicotinic acids, we further examined the crystal structure of 6-hydroxynicotinic acid, a structural isomer of II in this report.
The asymmetric unit of (I), (Fig. 1), contains four molecules and all the molecules have an almost perfectly planar conformation. Like II, the molecule was measured as 1,6-dihydro-6-oxo-3-pyridinecarboxylic acid, the tautomer of 6-hydroxynicotinic acid. Unlike 1,2-dihydro-2-oxo-3-pyridinecarboxylic acid, whose carboxyl group has an anti conformation, the carboxyl group of I has a syn conformation.
The hydrogen bonding network in the crystal (I) is more complicated compared with that of 1,2-dihydro-2-oxo-3-pyridinecarboxylic acid. In the title compound, the hydrogen bonding network can be described as hydrogen-bonded sheets along the [0 0 1] direction via intermolecular N—H···O and O—H···O hydrogen bonds (Table 1, Fig. 2). Careful examination of the sheets finds that each sheet consists of inter-connected dimers created by R22(8) N—H···O hydrogen-bonded motifs and infinite chains formed by C(7) hydrogen-bonded motifs according to Etter's notation. Alternately, these sheets can be viewed as infinitely fused 32-membered hydrogen bonded rings.