Acta Cryst. (2010). E66, o695 [ doi:10.1107/S1600536810006604 ]
In the title compound, C6H8NO2+·Cl-, intermolecular O-H
Cl and N-HCl hydrogen bonds are observed in which each chloride anion links three adjacent cations into a hydrogen-bond network.
The H1A atom bonded with atom O1 was located in the difference synthesis and were refined isotropically. The other H atoms were placed in geometrically idealized positions and refined as riding, with C—H = 0.93–0.98 Å, N—H = 0.86 Å and O—H = 0.96 Å, Uiso(H) = 1.2Ueq(C), Uiso(H) = 1.2Ueq(N) and Uiso(H) = 1.5Ueq(O).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./bg2326fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./bg2326fig2thm.gif)
| Fig. 2. Perspective view of the hydrogen bonding interactions in the crystal packing of (I), where the hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) x - 1, -y+3/2, z + 1/2; (ii) x, y1/2, z + 1; (iii) x, -y+3/2, z + 1/2.] |
| C6H8NO2+·Cl− | F(000) = 336 |
| Mr = 161.58 | Dx = 1.455 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 776 reflections |
| a = 4.6879 (7) Å | θ = 2.4–21.0° |
| b = 15.557 (2) Å | µ = 0.45 mm−1 |
| c = 10.1199 (14) Å | T = 291 K |
| β = 91.181 (2)° | Block, colourless |
| V = 737.88 (18) Å3 | 0.12 × 0.12 × 0.10 mm |
| Z = 4 |
| Bruker SMART 1K CCD area-detector diffractometer | 1303 independent reflections |
| Radiation source: fine-focus sealed tube | 842 reflections with I > 2σ(I) |
| graphite | Rint = 0.058 |
| φ and ω scans | θmax = 25.0°, θmin = 2.4° |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −5→5 |
| Tmin = 0.948, Tmax = 0.956 | k = −12→18 |
| 3676 measured reflections | l = −12→10 |
| 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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.075 | H atoms treated by a mixture of independent and constrained refinement |
| S = 0.89 | w = 1/[σ2(Fo2) + (0.0272P)2] where P = (Fo2 + 2Fc2)/3 |
| 1303 reflections | (Δ/σ)max = 0.001 |
| 99 parameters | Δρmax = 0.22 e Å−3 |
| 2 restraints | Δρmin = −0.23 e Å−3 |
| C6H8NO2+·Cl− | V = 737.88 (18) Å3 |
| Mr = 161.58 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 4.6879 (7) Å | µ = 0.45 mm−1 |
| b = 15.557 (2) Å | T = 291 K |
| c = 10.1199 (14) Å | 0.12 × 0.12 × 0.10 mm |
| β = 91.181 (2)° |
| Bruker SMART 1K CCD area-detector diffractometer | 1303 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2000) | 842 reflections with I > 2σ(I) |
| Tmin = 0.948, Tmax = 0.956 | Rint = 0.058 |
| 3676 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.075 | Δρmax = 0.22 e Å−3 |
| S = 0.89 | Δρmin = −0.23 e Å−3 |
| 1303 reflections | Absolute structure: ? |
| 99 parameters | Flack parameter: ? |
| 2 restraints | Rogers parameter: ? |
Experimental. The structure was solved by direct methods (Bruker, 2000) and successive difference Fourier syntheses. |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
| C1 | 0.0342 (4) | 0.62701 (15) | 0.8930 (2) | 0.0395 (6) | |
| C2 | 0.1167 (5) | 0.54999 (16) | 0.8429 (2) | 0.0469 (6) | |
| H2 | 0.2515 | 0.5168 | 0.8883 | 0.056* | |
| C3 | 0.0002 (5) | 0.52104 (16) | 0.7246 (2) | 0.0544 (7) | |
| H3 | 0.0549 | 0.4681 | 0.6906 | 0.065* | |
| C4 | −0.1975 (5) | 0.57099 (17) | 0.6572 (2) | 0.0553 (7) | |
| H4 | −0.2792 | 0.5519 | 0.5780 | 0.066* | |
| C5 | −0.2716 (5) | 0.64860 (17) | 0.7082 (2) | 0.0504 (7) | |
| H5 | −0.4015 | 0.6836 | 0.6630 | 0.060* | |
| C6 | 0.1322 (5) | 0.66291 (15) | 1.0257 (2) | 0.0448 (6) | |
| H6 | 0.0102 | 0.6382 | 1.0935 | 0.054* | |
| Cl1 | 0.51126 (13) | 0.65293 (4) | 0.34503 (6) | 0.0572 (2) | |
| H1A | 0.442 (6) | 0.6405 (18) | 1.1316 (11) | 0.090 (11)* | |
| H2A | 0.211 (5) | 0.7784 (16) | 0.978 (2) | 0.080 (11)* | |
| N1 | −0.1571 (4) | 0.67433 (12) | 0.82335 (17) | 0.0424 (5) | |
| H1 | −0.2077 | 0.7233 | 0.8546 | 0.051* | |
| O1 | 0.4092 (3) | 0.63308 (12) | 1.04924 (17) | 0.0573 (5) | |
| O2 | 0.1066 (4) | 0.75152 (12) | 1.03217 (17) | 0.0567 (5) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C1 | 0.0371 (13) | 0.0428 (15) | 0.0389 (13) | −0.0011 (11) | 0.0022 (11) | 0.0061 (11) |
| C2 | 0.0486 (14) | 0.0414 (15) | 0.0508 (15) | 0.0054 (12) | 0.0005 (12) | 0.0027 (12) |
| C3 | 0.0671 (17) | 0.0424 (16) | 0.0537 (17) | −0.0014 (14) | 0.0030 (14) | −0.0052 (13) |
| C4 | 0.0661 (18) | 0.0557 (18) | 0.0439 (15) | −0.0126 (15) | −0.0050 (13) | −0.0025 (13) |
| C5 | 0.0529 (16) | 0.0540 (17) | 0.0441 (15) | −0.0023 (13) | −0.0062 (12) | 0.0083 (13) |
| C6 | 0.0431 (14) | 0.0467 (16) | 0.0446 (14) | 0.0032 (13) | 0.0011 (11) | 0.0031 (12) |
| Cl1 | 0.0683 (5) | 0.0469 (4) | 0.0559 (4) | −0.0043 (3) | −0.0107 (3) | −0.0036 (3) |
| N1 | 0.0464 (12) | 0.0389 (12) | 0.0418 (12) | 0.0010 (10) | 0.0008 (9) | 0.0013 (9) |
| O1 | 0.0480 (11) | 0.0753 (14) | 0.0483 (12) | 0.0133 (9) | −0.0086 (9) | −0.0063 (9) |
| O2 | 0.0670 (13) | 0.0478 (12) | 0.0551 (12) | 0.0021 (10) | −0.0013 (10) | −0.0084 (9) |
| C1—N1 | 1.348 (3) | C5—N1 | 1.334 (3) |
| C1—C2 | 1.360 (3) | C5—H5 | 0.9300 |
| C1—C6 | 1.518 (3) | C6—O2 | 1.385 (3) |
| C2—C3 | 1.381 (3) | C6—O1 | 1.395 (3) |
| C2—H2 | 0.9300 | C6—H6 | 0.9800 |
| C3—C4 | 1.379 (3) | N1—H1 | 0.8600 |
| C3—H3 | 0.9300 | O1—H1A | 0.852 (10) |
| C4—C5 | 1.361 (3) | O2—H2A | 0.853 (10) |
| C4—H4 | 0.9300 | ||
| N1—C1—C2 | 118.5 (2) | N1—C5—H5 | 120.1 |
| N1—C1—C6 | 116.6 (2) | C4—C5—H5 | 120.1 |
| C2—C1—C6 | 124.8 (2) | O2—C6—O1 | 113.84 (19) |
| C1—C2—C3 | 120.0 (2) | O2—C6—C1 | 112.52 (18) |
| C1—C2—H2 | 120.0 | O1—C6—C1 | 106.99 (18) |
| C3—C2—H2 | 120.0 | O2—C6—H6 | 107.7 |
| C4—C3—C2 | 119.6 (2) | O1—C6—H6 | 107.7 |
| C4—C3—H3 | 120.2 | C1—C6—H6 | 107.7 |
| C2—C3—H3 | 120.2 | C5—N1—C1 | 123.0 (2) |
| C5—C4—C3 | 119.1 (2) | C5—N1—H1 | 118.5 |
| C5—C4—H4 | 120.4 | C1—N1—H1 | 118.5 |
| C3—C4—H4 | 120.4 | C6—O1—H1A | 105.8 (19) |
| N1—C5—C4 | 119.7 (2) | C6—O2—H2A | 114.0 (19) |
| N1—C1—C2—C3 | −1.4 (3) | C2—C1—C6—O2 | 157.6 (2) |
| C6—C1—C2—C3 | 175.9 (2) | N1—C1—C6—O1 | −150.91 (18) |
| C1—C2—C3—C4 | 0.6 (4) | C2—C1—C6—O1 | 31.8 (3) |
| C2—C3—C4—C5 | 0.8 (4) | C4—C5—N1—C1 | 0.7 (3) |
| C3—C4—C5—N1 | −1.4 (4) | C2—C1—N1—C5 | 0.7 (3) |
| N1—C1—C6—O2 | −25.2 (3) | C6—C1—N1—C5 | −176.7 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···Cl1i | 0.85 (1) | 2.24 (1) | 3.089 (2) | 176 (2) |
| O1—H1A···Cl1ii | 0.85 (1) | 2.19 (1) | 3.0374 (18) | 177 (3) |
| N1—H1···Cl1iii | 0.86 | 2.33 | 3.115 (2) | 151 |
| Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z+1; (iii) x−1, −y+3/2, z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2A···Cl1i | 0.85 (1) | 2.24 (1) | 3.089 (2) | 176 (2) |
| O1—H1A···Cl1ii | 0.85 (1) | 2.19 (1) | 3.0374 (18) | 177 (3) |
| N1—H1···Cl1iii | 0.86 | 2.33 | 3.115 (2) | 151 |
| Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z+1; (iii) x−1, −y+3/2, z+1/2. |
WH acknowledges the National Natural Science Foundation of China (No. 20871065) and the Jiangsu Province Department of Science and Technology (No. BK2009226) for financial aid.
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Mantero, D. G., Altaf, M., Neels, A. & Stoeckli-Evans, H. (2006). Acta Cryst. E62, o5204–o5206.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
The crystal structure of pyridin-4-ylmethanediol, namely the hydrated form of isonicotinaldehyde has been previously reported (Mantero et al., 2006). In this paper, we report the X-ray single-crystal structure of pyridin-2-ylmethanediol-1-ium chloride (I).
The molecular structure of (I) is illustrated in Fig. 1. The two hydroxyl groups lie at the same side of the aromatic ring. In the crystal packing, intermolecular O—H···Cl and N—H···Cl hydrogen bonding interactions are observed where every chloride anion links three adjacent molecules into a hydrogen-bond sustained network (Fig. 2).