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access3-(2-Hydroxybenzylideneamino)benzonitrile
aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: xuhj@seu.edu.cn
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)°.
Related literature
For related crystal structures, see: Kosar et al. (2005![[Ko˛sar, B., Albayrak, C., Odabaşoğlu, M. & Büyükgüngör (2005). Acta Cryst. E61, o2106-o2108.]](../../../../../../logos/arrows/e_arr.gif "Ko˛sar, B., Albayrak, C., Odabaşoğlu, M. & Büyükgüngör (2005). Acta Cryst. E61, o2106-o2108.")
); Cheng et al. (2005, 2006).
![[Scheme 1]](cv2384scheme1.gif)
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2005); cell CrystalClear; data reduction: CrystalClear; 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.
Supporting information
contains datablocks I, global. DOI: 10.1107/S1600536808005242/cv2384sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808005242/cv2384Isup2.hkl
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 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 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 | F(000) = 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 = 3.0–27.6° |
| b = 3.9211 (8) Å | µ = 0.09 mm−1 |
| c = 10.773 (2) Å | T = 293 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) |
| Graphite monochromator | Rint = 0.116 |
| Detector resolution: 13.6612 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
| 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 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0413P)2] where P = (Fo2 + 2Fc2)/3 |
| 1339 reflections | (Δ/σ)max < 0.001 |
| 160 parameters | Δρmax = 0.15 e Å−3 |
| 2 restraints | Δρmin = −0.16 e Å−3 |
| C14H10N2O | V = 1115.1 (4) Å3 |
| Mr = 222.24 | Z = 4 |
| Orthorhombic, Pca21 | Mo Kα radiation |
| a = 26.397 (5) Å | µ = 0.09 mm−1 |
| b = 3.9211 (8) Å | T = 293 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 | 2 restraints |
| wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | Δρmax = 0.15 e Å−3 |
| 1339 reflections | Δρmin = −0.16 e Å−3 |
| 160 parameters |
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) |
Experimental details
| Crystal data | |
| Chemical formula | C14H10N2O |
| Mr | 222.24 |
| Crystal system, space group | Orthorhombic, Pca21 |
| Temperature (K) | 293 |
| a, b, c (Å) | 26.397 (5), 3.9211 (8), 10.773 (2) |
| V (Å3) | 1115.1 (4) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.09 |
| Crystal size (mm) | 0.22 × 0.05 × 0.05 |
| Data collection | |
| Diffractometer | Rigaku Mercury2 diffractometer |
| Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
| Tmin, Tmax | 0.812, 1.00 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 9995, 1339, 901 |
| Rint | 0.116 |
| (sin θ/λ)max (Å−1) | 0.649 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.121, 1.05 |
| No. of reflections | 1339 |
| No. of parameters | 160 |
| No. of restraints | 2 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
| 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) |
Acknowledgements
HJX acknowledges a Start-up Grant from Southeast University, People's Republic of China.
References
Cheng, K., You, Z.-L., Li, Y.-G. & Zhu, H.-L. (2005). Acta Cryst. E61, o1137–o1138. Web of Science CrossRef IUCr Journals Google Scholar
Cheng, K., Zhu, H. L., Li, Z. B. & Yan, Z. (2006). Acta Cryst. E62, o2417–o2418. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ko˛sar, B., Albayrak, C., Odabaşoğlu, M. & Büyükgüngör (2005). Acta Cryst. E61, o2106–o2108. Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
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.