Acta Cryst. (2008). E64, o638 [ doi:10.1107/S1600536808005242 ]
In the title molecule, C14H10N2O, an intramolecular O-H
N hydrogen bond contributes to the essential coplanarity of the two benzene rings, which form a dihedral angle of 6.04 (18)°.
3-Aminobenzonitrile and salicylaldehyde were available commercially and were used without further purification. 3-Aminobenzonitrile (1.18 g, 10 mmol) and salicylaldehyde (1.22 g, 10 mmol) were dissolved in ethanol (20 ml). The mixture was heated to reflux for 4 h, then cooled to room temperature overnight and large amounts of a yellow precipitate were formed. Yellow crystals were obtained by recrystallization from ethyl alcohol (yield: 82%). For the X-ray diffraction analysis, suitable single crystals were obtained after one week by slow evaporation from an ethyl alcohol solution.
C-bound H atoms were geometrically positioned (C—H 0.93 Å) and refined as riding with Uiso(H)= 1.2Ueq(C). Atom H1B was located on a difference map and refined isotropically with bon restraint O1—H1B = 0.82 (2) Å. In the absence of significant anomalous scatterers, 1124 Friedel pairs were merged.
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./cv2384fig1thm.gif)
| Fig. 1. The molecular structure of the title compound with atomic numbering and displacement ellipsoids drawn at the 30% probability level. |
| C14H10N2O | F000 = 464 |
| Mr = 222.24 | Dx = 1.324 Mg m−3 |
| Orthorhombic, Pca21 | Mo Kα radiation λ = 0.71073 Å |
| Hall symbol: P 2c -2ac | Cell parameters from 8294 reflections |
| a = 26.397 (5) Å | θ = 3.0–27.6º |
| b = 3.9211 (8) Å | µ = 0.09 mm−1 |
| c = 10.773 (2) Å | T = 293 (2) K |
| V = 1115.1 (4) Å3 | Stick, yellow |
| Z = 4 | 0.22 × 0.05 × 0.05 mm |
| Rigaku Mercury2 diffractometer | 1339 independent reflections |
| Radiation source: fine-focus sealed tube | 901 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.116 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5º |
| T = 293(2) K | θmin = 3.1º |
| ω scans | h = −34→34 |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −5→5 |
| Tmin = 0.812, Tmax = 1.00 | l = −13→13 |
| 9995 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0413P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 1339 reflections | Δρmax = 0.15 e Å−3 |
| 160 parameters | Δρmin = −0.16 e Å−3 |
| 2 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| C14H10N2O | V = 1115.1 (4) Å3 |
| Mr = 222.24 | Z = 4 |
| Orthorhombic, Pca21 | Mo Kα |
| a = 26.397 (5) Å | µ = 0.09 mm−1 |
| b = 3.9211 (8) Å | T = 293 (2) K |
| c = 10.773 (2) Å | 0.22 × 0.05 × 0.05 mm |
| Rigaku Mercury2 diffractometer | 1339 independent reflections |
| Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 901 reflections with I > 2σ(I) |
| Tmin = 0.812, Tmax = 1.00 | Rint = 0.116 |
| 9995 measured reflections |
| R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.121 | Δρmax = 0.15 e Å−3 |
| S = 1.05 | Δρmin = −0.16 e Å−3 |
| 1339 reflections | Absolute structure: ? |
| 160 parameters | Flack parameter: ? |
| 2 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 | ||
| N1 | 0.45687 (11) | 0.2218 (7) | 0.2697 (3) | 0.0473 (8) | |
| C1 | 0.54425 (12) | 0.2407 (8) | 0.3273 (3) | 0.0427 (8) | |
| C9 | 0.37076 (12) | 0.2616 (9) | 0.2071 (3) | 0.0457 (9) | |
| H9A | 0.3823 | 0.3718 | 0.1360 | 0.055* | |
| C6 | 0.57995 (14) | 0.1614 (9) | 0.4188 (3) | 0.0559 (10) | |
| H6A | 0.5694 | 0.0602 | 0.4924 | 0.067* | |
| C8 | 0.40534 (12) | 0.1480 (8) | 0.2952 (3) | 0.0451 (8) | |
| C7 | 0.49124 (12) | 0.1608 (8) | 0.3501 (3) | 0.0460 (9) | |
| H7A | 0.4821 | 0.0624 | 0.4254 | 0.055* | |
| C3 | 0.61133 (14) | 0.4649 (10) | 0.2017 (3) | 0.0570 (11) | |
| H3A | 0.6223 | 0.5715 | 0.1294 | 0.068* | |
| C2 | 0.56072 (13) | 0.3894 (9) | 0.2167 (3) | 0.0468 (9) | |
| C12 | 0.33597 (14) | −0.0682 (10) | 0.4162 (4) | 0.0601 (10) | |
| H12A | 0.3245 | −0.1800 | 0.4869 | 0.072* | |
| C10 | 0.31905 (13) | 0.2118 (9) | 0.2243 (3) | 0.0510 (10) | |
| C11 | 0.30193 (13) | 0.0476 (9) | 0.3297 (3) | 0.0572 (11) | |
| H11A | 0.2674 | 0.0157 | 0.3421 | 0.069* | |
| C14 | 0.28378 (13) | 0.3427 (10) | 0.1343 (4) | 0.0585 (10) | |
| O1 | 0.52789 (11) | 0.4688 (8) | 0.1250 (3) | 0.0683 (8) | |
| C5 | 0.63050 (14) | 0.2312 (10) | 0.4013 (4) | 0.0629 (11) | |
| H5A | 0.6540 | 0.1756 | 0.4622 | 0.076* | |
| C4 | 0.64585 (14) | 0.3839 (10) | 0.2928 (4) | 0.0632 (11) | |
| H4A | 0.6800 | 0.4331 | 0.2808 | 0.076* | |
| C13 | 0.38733 (13) | −0.0193 (10) | 0.3986 (3) | 0.0542 (10) | |
| H13A | 0.4101 | −0.1006 | 0.4575 | 0.065* | |
| N2 | 0.25591 (14) | 0.4542 (10) | 0.0648 (4) | 0.0896 (13) | |
| H1B | 0.4999 (10) | 0.396 (12) | 0.145 (7) | 0.13 (2)* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0426 (18) | 0.0517 (18) | 0.0474 (16) | 0.0006 (13) | −0.0038 (14) | −0.0007 (13) |
| C1 | 0.038 (2) | 0.0449 (17) | 0.045 (2) | 0.0021 (14) | 0.0015 (17) | −0.0035 (16) |
| C9 | 0.042 (2) | 0.048 (2) | 0.046 (2) | 0.0029 (16) | 0.0022 (17) | −0.0027 (17) |
| C6 | 0.053 (2) | 0.058 (2) | 0.057 (2) | 0.0006 (18) | −0.005 (2) | 0.0031 (19) |
| C8 | 0.0392 (19) | 0.0456 (19) | 0.051 (2) | −0.0018 (15) | 0.0032 (17) | −0.0088 (17) |
| C7 | 0.052 (2) | 0.0445 (19) | 0.042 (2) | 0.0000 (16) | 0.0045 (17) | 0.0015 (17) |
| C3 | 0.054 (3) | 0.061 (3) | 0.056 (2) | −0.0065 (18) | 0.0091 (19) | −0.0002 (19) |
| C2 | 0.047 (2) | 0.051 (2) | 0.042 (2) | −0.0009 (16) | 0.0012 (16) | −0.0012 (18) |
| C12 | 0.056 (2) | 0.065 (3) | 0.060 (2) | −0.0083 (19) | 0.006 (2) | 0.006 (2) |
| C10 | 0.042 (2) | 0.054 (2) | 0.057 (2) | 0.0035 (17) | 0.0024 (19) | −0.0148 (19) |
| C11 | 0.0399 (19) | 0.061 (2) | 0.071 (3) | −0.0074 (17) | 0.0068 (19) | −0.013 (2) |
| C14 | 0.044 (2) | 0.065 (3) | 0.067 (2) | 0.0038 (18) | −0.006 (2) | −0.011 (2) |
| O1 | 0.0590 (17) | 0.092 (2) | 0.0540 (15) | −0.0015 (16) | −0.0059 (17) | 0.0190 (16) |
| C5 | 0.049 (2) | 0.070 (3) | 0.070 (3) | 0.007 (2) | −0.011 (2) | 0.002 (2) |
| C4 | 0.047 (2) | 0.064 (2) | 0.079 (3) | −0.0066 (19) | 0.004 (2) | −0.008 (2) |
| C13 | 0.047 (2) | 0.060 (2) | 0.056 (2) | −0.0005 (17) | 0.0015 (18) | 0.007 (2) |
| N2 | 0.066 (2) | 0.097 (3) | 0.105 (3) | 0.012 (2) | −0.032 (2) | −0.004 (2) |
| N1—C7 | 1.277 (4) | C3—H3A | 0.9300 |
| N1—C8 | 1.418 (4) | C2—O1 | 1.351 (4) |
| C1—C2 | 1.396 (4) | C12—C11 | 1.372 (5) |
| C1—C6 | 1.398 (5) | C12—C13 | 1.382 (5) |
| C1—C7 | 1.455 (4) | C12—H12A | 0.9300 |
| C9—C8 | 1.390 (4) | C10—C11 | 1.381 (5) |
| C9—C10 | 1.391 (4) | C10—C14 | 1.439 (5) |
| C9—H9A | 0.9300 | C11—H11A | 0.9300 |
| C6—C5 | 1.375 (5) | C14—N2 | 1.137 (5) |
| C6—H6A | 0.9300 | O1—H1B | 0.82 (2) |
| C8—C13 | 1.377 (5) | C5—C4 | 1.374 (5) |
| C7—H7A | 0.9300 | C5—H5A | 0.9300 |
| C3—C4 | 1.376 (5) | C4—H4A | 0.9300 |
| C3—C2 | 1.378 (4) | C13—H13A | 0.9300 |
| C7—N1—C8 | 120.8 (3) | C3—C2—C1 | 119.5 (3) |
| C2—C1—C6 | 119.0 (3) | C11—C12—C13 | 120.2 (3) |
| C2—C1—C7 | 122.2 (3) | C11—C12—H12A | 119.9 |
| C6—C1—C7 | 118.8 (3) | C13—C12—H12A | 119.9 |
| C8—C9—C10 | 120.5 (3) | C11—C10—C9 | 119.8 (3) |
| C8—C9—H9A | 119.7 | C11—C10—C14 | 120.6 (3) |
| C10—C9—H9A | 119.7 | C9—C10—C14 | 119.6 (4) |
| C5—C6—C1 | 120.9 (4) | C12—C11—C10 | 119.9 (3) |
| C5—C6—H6A | 119.6 | C12—C11—H11A | 120.1 |
| C1—C6—H6A | 119.6 | C10—C11—H11A | 120.1 |
| C13—C8—C9 | 118.6 (3) | N2—C14—C10 | 178.2 (5) |
| C13—C8—N1 | 125.8 (3) | C2—O1—H1B | 108 (5) |
| C9—C8—N1 | 115.6 (3) | C4—C5—C6 | 119.3 (4) |
| N1—C7—C1 | 121.9 (3) | C4—C5—H5A | 120.4 |
| N1—C7—H7A | 119.0 | C6—C5—H5A | 120.4 |
| C1—C7—H7A | 119.0 | C3—C4—C5 | 120.8 (3) |
| C4—C3—C2 | 120.5 (4) | C3—C4—H4A | 119.6 |
| C4—C3—H3A | 119.7 | C5—C4—H4A | 119.6 |
| C2—C3—H3A | 119.7 | C12—C13—C8 | 121.0 (3) |
| O1—C2—C3 | 119.1 (3) | C12—C13—H13A | 119.5 |
| O1—C2—C1 | 121.4 (3) | C8—C13—H13A | 119.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1B···N1 | 0.82 (2) | 1.89 (4) | 2.623 (4) | 149 (7) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1B···N1 | 0.82 (2) | 1.89 (4) | 2.623 (4) | 149 (7) |
HJX acknowledges a Start-up Grant from Southeast University, People's Republic of China.
Cheng, K., You, Z.-L., Li, Y.-G. & Zhu, H.-L. (2005). Acta Cryst. E61, o1137–o1138.
Cheng, K., Zhu, H. L., Lib, Z. B. & Yan, Z. (2006). Acta Cryst. E62, o2156–o2157. Please check reference. Do you mean Cheng, K., Zhu, H. L., Li, Z. B. & Yan, Z. (2006). Acta Cryst.E62, o2417–o2418?
Ko˛sar, B., Albayrak, C., Odabaşoğlu, M. & Büyükgüngör (2005). Acta Cryst. E61, o2106–o2108.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Schiff base compounds have attracted great attention for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism, photochromism and thermochromism. Here, we report the crystal structure of the title compound.
In the title compound (Fig. 1), all bond lengths are within normal ranges. The C7=N1 bond length of 1.277 (4)Å is a typical double bond, similar to the corresponding bond lengths in 4-methoxy-2-[(4-nitrophenyl)iminomethyl]phenol (Kosar et al., 2005). The molecule is almost planar and displays a trans configuration with respect to the C7=N1 double bond. The dihedral angle between the benzene rings is 6.04 (18)°. Strong intramolecular O—H···N hydrogen-bond interaction (Talbe I), similar to the reported earlier (Cheng et al., 2005, 2006), is observed in the molecule.