Acta Cryst. (2008). E64, o1918 [ doi:10.1107/S1600536808028481 ]
In molecule of the title compound, C16H14N2O2, the two aromatic rings form a dihedral angle of 6.93 (3)° and an intramolecular N-H
O hydrogen bond occurs. In the crystal structure, intermolecular O-HO hydrogen bonds link the molecules into zigzag chains running in the [10
] direction.
The title compound was synthesized by the reaction of 2-Hydroxy-benzoic acid hydrazide(1 mmol, 152.2 mg) with 3-Phenyl-propenal (1 mmol, 132.2 mg) in ethanol(20 ml) under reflux conditions (348 K) for 6 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After six days colorless crystals suitable for X-ray diffraction study were obtained. Yield, 226.3 mg, 85%. m.p. 239–241 K. Analysis calculated for C16H14N2O2: C 72.16, H 5.30, N 10.52%; found: C 71.73, H 5.34, N 10.48%.
All H atoms were placed in idealized positions (C—H = 0.93— 0.97 Å, N—H = 0.86 Å) and refined as riding, with Uiso(H) = 1.2 or 1.5Ueq(C, N).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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]](./cv2440fig1thm.gif)
| Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. |
| C16H14N2O2 | F(000) = 560 |
| Mr = 266.29 | Dx = 1.298 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 932 reflections |
| a = 4.8892 (6) Å | θ = 3.6–21.4° |
| b = 26.563 (3) Å | µ = 0.09 mm−1 |
| c = 10.7367 (13) Å | T = 295 K |
| β = 102.305 (2)° | Block, colourless |
| V = 1362.4 (3) Å3 | 0.15 × 0.12 × 0.10 mm |
| Z = 4 |
| Bruker SMART CCD area-detector diffractometer | 2395 independent reflections |
| Radiation source: fine-focus sealed tube | 1354 reflections with I > 2σ(I) |
| graphite | Rint = 0.038 |
| φ and ω scans | θmax = 25.1°, θmin = 2.5° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→5 |
| Tmin = 0.987, Tmax = 0.991 | k = −21→31 |
| 7141 measured reflections | l = −12→12 |
| 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)] = 0.047 | H-atom parameters constrained |
| wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 2395 reflections | Δρmax = 0.14 e Å−3 |
| 183 parameters | Δρmin = −0.13 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.008 (2) |
| C16H14N2O2 | V = 1362.4 (3) Å3 |
| Mr = 266.29 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 4.8892 (6) Å | µ = 0.09 mm−1 |
| b = 26.563 (3) Å | T = 295 K |
| c = 10.7367 (13) Å | 0.15 × 0.12 × 0.10 mm |
| β = 102.305 (2)° |
| Bruker SMART CCD area-detector diffractometer | 2395 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1354 reflections with I > 2σ(I) |
| Tmin = 0.987, Tmax = 0.991 | Rint = 0.038 |
| 7141 measured reflections | θmax = 25.1° |
| R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
| wR(F2) = 0.124 | Δρmax = 0.14 e Å−3 |
| S = 1.05 | Δρmin = −0.13 e Å−3 |
| 2395 reflections | Absolute structure: ? |
| 183 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 | ||
| O1 | 0.5440 (4) | 0.26610 (6) | 0.08347 (14) | 0.0702 (5) | |
| H1 | 0.6201 | 0.2633 | 0.0227 | 0.105* | |
| O2 | 0.4213 (4) | 0.27755 (6) | 0.45173 (13) | 0.0687 (5) | |
| N1 | 0.2766 (4) | 0.24015 (6) | 0.26236 (15) | 0.0508 (5) | |
| H1A | 0.2861 | 0.2378 | 0.1835 | 0.061* | |
| N2 | 0.1041 (4) | 0.20892 (7) | 0.31262 (16) | 0.0513 (5) | |
| C1 | 0.6656 (4) | 0.30391 (8) | 0.15959 (19) | 0.0483 (6) | |
| C2 | 0.6118 (4) | 0.30864 (8) | 0.28157 (18) | 0.0450 (5) | |
| C3 | 0.7379 (5) | 0.34777 (9) | 0.3569 (2) | 0.0634 (7) | |
| H3 | 0.7048 | 0.3513 | 0.4386 | 0.076* | |
| C4 | 0.9102 (6) | 0.38164 (9) | 0.3154 (2) | 0.0736 (8) | |
| H4 | 0.9898 | 0.4080 | 0.3676 | 0.088* | |
| C5 | 0.9638 (5) | 0.37611 (9) | 0.1959 (2) | 0.0662 (7) | |
| H5 | 1.0826 | 0.3986 | 0.1674 | 0.079* | |
| C6 | 0.8438 (5) | 0.33774 (9) | 0.1184 (2) | 0.0606 (7) | |
| H6 | 0.8818 | 0.3343 | 0.0375 | 0.073* | |
| C7 | 0.4304 (5) | 0.27445 (8) | 0.33872 (19) | 0.0476 (6) | |
| C8 | −0.0380 (5) | 0.17709 (8) | 0.2358 (2) | 0.0529 (6) | |
| H8 | −0.0220 | 0.1766 | 0.1510 | 0.064* | |
| C9 | −0.2215 (5) | 0.14220 (8) | 0.2788 (2) | 0.0530 (6) | |
| H9 | −0.2416 | 0.1442 | 0.3628 | 0.064* | |
| C10 | −0.3630 (5) | 0.10743 (9) | 0.2044 (2) | 0.0576 (6) | |
| H10 | −0.3419 | 0.1072 | 0.1203 | 0.069* | |
| C11 | −0.5490 (5) | 0.06929 (8) | 0.2383 (2) | 0.0529 (6) | |
| C12 | −0.6805 (5) | 0.03509 (10) | 0.1480 (2) | 0.0739 (8) | |
| H12 | −0.6499 | 0.0369 | 0.0655 | 0.089* | |
| C13 | −0.8563 (6) | −0.00161 (11) | 0.1777 (3) | 0.0842 (9) | |
| H13 | −0.9404 | −0.0244 | 0.1156 | 0.101* | |
| C14 | −0.9071 (6) | −0.00457 (10) | 0.2973 (3) | 0.0761 (8) | |
| H14 | −1.0287 | −0.0288 | 0.3169 | 0.091* | |
| C15 | −0.7772 (6) | 0.02847 (10) | 0.3879 (3) | 0.0807 (8) | |
| H15 | −0.8084 | 0.0264 | 0.4702 | 0.097* | |
| C16 | −0.6002 (5) | 0.06496 (9) | 0.3590 (2) | 0.0670 (7) | |
| H16 | −0.5137 | 0.0871 | 0.4223 | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0858 (13) | 0.0893 (13) | 0.0482 (9) | −0.0339 (10) | 0.0428 (9) | −0.0229 (9) |
| O2 | 0.0900 (14) | 0.0857 (12) | 0.0392 (9) | −0.0137 (9) | 0.0337 (8) | −0.0060 (8) |
| N1 | 0.0615 (13) | 0.0615 (12) | 0.0363 (9) | −0.0068 (10) | 0.0257 (9) | 0.0017 (9) |
| N2 | 0.0587 (13) | 0.0596 (12) | 0.0424 (10) | −0.0030 (10) | 0.0263 (9) | 0.0069 (9) |
| C1 | 0.0531 (15) | 0.0568 (14) | 0.0384 (12) | −0.0055 (11) | 0.0174 (10) | −0.0034 (10) |
| C2 | 0.0509 (15) | 0.0505 (13) | 0.0366 (11) | 0.0016 (11) | 0.0158 (10) | 0.0003 (10) |
| C3 | 0.083 (2) | 0.0703 (17) | 0.0416 (13) | −0.0132 (14) | 0.0247 (12) | −0.0088 (12) |
| C4 | 0.097 (2) | 0.0700 (18) | 0.0568 (16) | −0.0233 (15) | 0.0219 (15) | −0.0121 (13) |
| C5 | 0.0740 (19) | 0.0696 (17) | 0.0575 (15) | −0.0225 (14) | 0.0192 (14) | 0.0020 (13) |
| C6 | 0.0701 (18) | 0.0765 (17) | 0.0412 (12) | −0.0134 (13) | 0.0252 (12) | 0.0026 (12) |
| C7 | 0.0552 (15) | 0.0547 (14) | 0.0383 (12) | 0.0047 (11) | 0.0218 (11) | 0.0002 (11) |
| C8 | 0.0614 (17) | 0.0631 (15) | 0.0377 (12) | −0.0015 (12) | 0.0183 (11) | 0.0042 (11) |
| C9 | 0.0580 (16) | 0.0613 (15) | 0.0440 (13) | −0.0030 (12) | 0.0205 (11) | 0.0068 (11) |
| C10 | 0.0613 (17) | 0.0687 (16) | 0.0444 (13) | −0.0007 (13) | 0.0151 (12) | 0.0044 (12) |
| C11 | 0.0528 (16) | 0.0563 (15) | 0.0501 (14) | 0.0024 (12) | 0.0118 (11) | 0.0029 (12) |
| C12 | 0.079 (2) | 0.086 (2) | 0.0571 (16) | −0.0149 (16) | 0.0147 (14) | −0.0071 (14) |
| C13 | 0.082 (2) | 0.082 (2) | 0.085 (2) | −0.0215 (16) | 0.0086 (17) | −0.0090 (16) |
| C14 | 0.0696 (19) | 0.0665 (19) | 0.093 (2) | −0.0088 (14) | 0.0189 (16) | 0.0139 (16) |
| C15 | 0.092 (2) | 0.082 (2) | 0.0768 (18) | −0.0177 (16) | 0.0376 (17) | 0.0056 (16) |
| C16 | 0.076 (2) | 0.0684 (17) | 0.0609 (16) | −0.0142 (13) | 0.0244 (14) | −0.0028 (12) |
| O1—C1 | 1.350 (2) | C8—C9 | 1.433 (3) |
| O1—H1 | 0.8200 | C8—H8 | 0.9300 |
| O2—C7 | 1.226 (2) | C9—C10 | 1.317 (3) |
| N1—C7 | 1.344 (2) | C9—H9 | 0.9300 |
| N1—N2 | 1.373 (2) | C10—C11 | 1.458 (3) |
| N1—H1A | 0.8600 | C10—H10 | 0.9300 |
| N2—C8 | 1.278 (2) | C11—C16 | 1.376 (3) |
| C1—C6 | 1.388 (3) | C11—C12 | 1.383 (3) |
| C1—C2 | 1.395 (3) | C12—C13 | 1.381 (3) |
| C2—C3 | 1.379 (3) | C12—H12 | 0.9300 |
| C2—C7 | 1.490 (3) | C13—C14 | 1.361 (3) |
| C3—C4 | 1.370 (3) | C13—H13 | 0.9300 |
| C3—H3 | 0.9300 | C14—C15 | 1.362 (3) |
| C4—C5 | 1.371 (3) | C14—H14 | 0.9300 |
| C4—H4 | 0.9300 | C15—C16 | 1.378 (3) |
| C5—C6 | 1.366 (3) | C15—H15 | 0.9300 |
| C5—H5 | 0.9300 | C16—H16 | 0.9300 |
| C6—H6 | 0.9300 | ||
| C1—O1—H1 | 109.5 | N2—C8—H8 | 119.6 |
| C7—N1—N2 | 118.73 (17) | C9—C8—H8 | 119.6 |
| C7—N1—H1A | 120.6 | C10—C9—C8 | 122.9 (2) |
| N2—N1—H1A | 120.6 | C10—C9—H9 | 118.6 |
| C8—N2—N1 | 116.17 (17) | C8—C9—H9 | 118.6 |
| O1—C1—C6 | 120.93 (18) | C9—C10—C11 | 127.6 (2) |
| O1—C1—C2 | 119.23 (18) | C9—C10—H10 | 116.2 |
| C6—C1—C2 | 119.8 (2) | C11—C10—H10 | 116.2 |
| C3—C2—C1 | 117.9 (2) | C16—C11—C12 | 117.0 (2) |
| C3—C2—C7 | 116.66 (18) | C16—C11—C10 | 122.8 (2) |
| C1—C2—C7 | 125.41 (19) | C12—C11—C10 | 120.2 (2) |
| C4—C3—C2 | 122.2 (2) | C13—C12—C11 | 121.4 (2) |
| C4—C3—H3 | 118.9 | C13—C12—H12 | 119.3 |
| C2—C3—H3 | 118.9 | C11—C12—H12 | 119.3 |
| C3—C4—C5 | 119.2 (2) | C14—C13—C12 | 120.4 (3) |
| C3—C4—H4 | 120.4 | C14—C13—H13 | 119.8 |
| C5—C4—H4 | 120.4 | C12—C13—H13 | 119.8 |
| C6—C5—C4 | 120.5 (2) | C13—C14—C15 | 119.0 (3) |
| C6—C5—H5 | 119.8 | C13—C14—H14 | 120.5 |
| C4—C5—H5 | 119.8 | C15—C14—H14 | 120.5 |
| C5—C6—C1 | 120.4 (2) | C14—C15—C16 | 120.8 (3) |
| C5—C6—H6 | 119.8 | C14—C15—H15 | 119.6 |
| C1—C6—H6 | 119.8 | C16—C15—H15 | 119.6 |
| O2—C7—N1 | 121.0 (2) | C11—C16—C15 | 121.3 (2) |
| O2—C7—C2 | 121.1 (2) | C11—C16—H16 | 119.3 |
| N1—C7—C2 | 117.84 (17) | C15—C16—H16 | 119.3 |
| N2—C8—C9 | 120.8 (2) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1 | 0.86 | 1.97 | 2.6348 (19) | 133. |
| O1—H1···O2i | 0.82 | 2.10 | 2.804 (3) | 144. |
| O1—H1···N2i | 0.82 | 2.36 | 3.057 (3) | 144. |
| Symmetry codes: (i) x+1/2, −y+1/2, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O1 | 0.86 | 1.97 | 2.6348 (19) | 133. |
| O1—H1···O2i | 0.82 | 2.10 | 2.804 (3) | 144. |
| Symmetry codes: (i) x+1/2, −y+1/2, z−1/2. |
This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y06-2-08).
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
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Garnovskii, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev. 126, 1–69.
Musie, G. T., Wei, M., Subramaniam, B. & Busch, D. H. (2001). Inorg. Chem. 40, 3336–3341.
Paul, S., Barik, A. K., Peng, S. M. & Kar, S. K. (2002). Inorg. Chem. 41, 5803–5809.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Shi, Z.-Q., Ji, N.-N., Zheng, Z.-B. & Li, J.-K. (2007). Acta Cryst. E63, o4561.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
In recent years, a number of Schiff-bases have been investigated in terms of their coordination chemistry (Garnovskii et al., 1993; Musie et al., 2001; Paul et al., 2002; Shi et al., 2007;) and biological systems (Anderson et al., 1997). In order to search for new Schiff-bases with higher bioactivity, the title compound, (I), was synthesized and its crystal structure determined.
In (I) (Fig. 1), the bond lengths and angles are in good agreement with the expected values (Allen et al., 1987). The intramolecular N—H···O hydrogen bond (Table 1) influences the molecular conformation. In the crystal, the molecules are linked into infinite chains along direction [10-1] by O—H···O hydrogen bonds (Table 1).