Acta Cryst. (2010). E66, o2692 [ doi:10.1107/S1600536810038365 ]
In the title compound, C21H18N2O2, the amino group is involved in an intramolecular N-H
O hydrogen bond. The rings make dihedral angles of 37.9 (2), 64.4 (2) and 83.6 (2)°. In the crystal, intermolecular O-HN and O-HO hydrogen bonds link the molecules into chains running along [100].
Benzoin (5 mmol), benzohydrazide (5 mmol) and methanol (10 ml) were mixed in 50 ml flask. After stirring for 2 h at 373 K, the resulting mixture was recrystalized from methanol, affording the title compound as a colorless crystalline solid. Elemental analysis: calculated for C21H18N2O2: C 76.34, H 5.49, N 8.48%; found: C 76.21, H 5.56, N 8.54%.
All H atoms were placed in geometrically idealized positions (N—H 0.86, O—H= 0.82 and C—H = 0.93–0.98 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2U-1.5Ueq of the parent atom. Due to the absence of any significant anomalous scatterers in the molecule, the 1239 Friedel pairs were merged before the final refinement.
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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]](./cv2764fig1thm.gif)
| Fig. 1. lThe molecular structure of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids. |
| C21H18N2O2 | Dx = 1.300 Mg m−3 |
| Mr = 330.37 | Mo Kα radiation, λ = 0.71073 Å |
| Orthorhombic, P212121 | Cell parameters from 1315 reflections |
| a = 7.7318 (8) Å | θ = 2.8–19.7° |
| b = 11.0653 (12) Å | µ = 0.09 mm−1 |
| c = 19.725 (2) Å | T = 298 K |
| V = 1687.5 (3) Å3 | Needle, colourless |
| Z = 4 | 0.41 × 0.16 × 0.13 mm |
| F(000) = 696 |
| Bruker SMART APEX CCD area-detector diffractometer | 1729 independent reflections |
| Radiation source: fine-focus sealed tube | 1051 reflections with I > 2σ(I) |
| graphite | Rint = 0.054 |
| phi and ω scans | θmax = 25.0°, θmin = 2.1° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | h = −9→8 |
| Tmin = 0.966, Tmax = 0.989 | k = −13→13 |
| 7865 measured reflections | l = −10→23 |
| 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.097 | H-atom parameters constrained |
| S = 1.07 | w = 1/[σ2(Fo2) + (0.0315P)2 + 0.2666P] where P = (Fo2 + 2Fc2)/3 |
| 1729 reflections | (Δ/σ)max < 0.001 |
| 226 parameters | Δρmax = 0.14 e Å−3 |
| 0 restraints | Δρmin = −0.16 e Å−3 |
| C21H18N2O2 | V = 1687.5 (3) Å3 |
| Mr = 330.37 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 7.7318 (8) Å | µ = 0.09 mm−1 |
| b = 11.0653 (12) Å | T = 298 K |
| c = 19.725 (2) Å | 0.41 × 0.16 × 0.13 mm |
| Bruker SMART APEX CCD area-detector diffractometer | 1729 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 1051 reflections with I > 2σ(I) |
| Tmin = 0.966, Tmax = 0.989 | Rint = 0.054 |
| 7865 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
| wR(F2) = 0.097 | Δρmax = 0.14 e Å−3 |
| S = 1.07 | Δρmin = −0.16 e Å−3 |
| 1729 reflections | Absolute structure: ? |
| 226 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 | ||
| N1 | 0.6095 (4) | 0.7285 (3) | 0.07224 (14) | 0.0466 (9) | |
| H1 | 0.5711 | 0.6582 | 0.0833 | 0.056* | |
| N2 | 0.6267 (4) | 0.7612 (3) | 0.00542 (16) | 0.0445 (9) | |
| O1 | 0.7060 (4) | 0.9121 (2) | 0.10546 (13) | 0.0550 (8) | |
| O2 | 0.3956 (3) | 0.5524 (2) | 0.02563 (13) | 0.0547 (8) | |
| H2 | 0.3161 | 0.5939 | 0.0110 | 0.082* | |
| C1 | 0.6551 (5) | 0.8107 (4) | 0.1207 (2) | 0.0441 (10) | |
| C2 | 0.6408 (5) | 0.7712 (3) | 0.19238 (19) | 0.0424 (10) | |
| C3 | 0.5837 (6) | 0.6586 (4) | 0.2127 (2) | 0.0538 (12) | |
| H3 | 0.5485 | 0.6025 | 0.1805 | 0.065* | |
| C4 | 0.5787 (6) | 0.6288 (4) | 0.2806 (2) | 0.0634 (13) | |
| H4 | 0.5385 | 0.5531 | 0.2939 | 0.076* | |
| C5 | 0.6324 (6) | 0.7097 (4) | 0.3285 (2) | 0.0638 (13) | |
| H5 | 0.6309 | 0.6890 | 0.3742 | 0.077* | |
| C6 | 0.6885 (7) | 0.8213 (4) | 0.3087 (2) | 0.0666 (14) | |
| H6 | 0.7230 | 0.8774 | 0.3410 | 0.080* | |
| C7 | 0.6939 (5) | 0.8510 (4) | 0.2408 (2) | 0.0543 (11) | |
| H7 | 0.7344 | 0.9267 | 0.2279 | 0.065* | |
| C8 | 0.5919 (5) | 0.6798 (3) | −0.03926 (18) | 0.0416 (10) | |
| C9 | 0.5351 (5) | 0.5513 (3) | −0.0227 (2) | 0.0443 (10) | |
| H9 | 0.4936 | 0.5132 | −0.0645 | 0.053* | |
| C10 | 0.6779 (5) | 0.4743 (3) | 0.00625 (18) | 0.0404 (10) | |
| C11 | 0.8474 (5) | 0.4869 (3) | −0.0146 (2) | 0.0513 (11) | |
| H11 | 0.8759 | 0.5474 | −0.0453 | 0.062* | |
| C12 | 0.9764 (6) | 0.4104 (4) | 0.0096 (2) | 0.0650 (13) | |
| H12 | 1.0900 | 0.4197 | −0.0050 | 0.078* | |
| C13 | 0.9345 (7) | 0.3213 (4) | 0.0551 (2) | 0.0692 (14) | |
| H13 | 1.0199 | 0.2697 | 0.0714 | 0.083* | |
| C14 | 0.7678 (7) | 0.3084 (4) | 0.0766 (3) | 0.0781 (15) | |
| H14 | 0.7401 | 0.2484 | 0.1077 | 0.094* | |
| C15 | 0.6399 (6) | 0.3839 (4) | 0.0523 (2) | 0.0622 (12) | |
| H15 | 0.5267 | 0.3739 | 0.0672 | 0.075* | |
| C16 | 0.6030 (5) | 0.7188 (3) | −0.11073 (19) | 0.0414 (10) | |
| C17 | 0.6508 (6) | 0.6403 (4) | −0.16168 (19) | 0.0547 (11) | |
| H17 | 0.6767 | 0.5604 | −0.1512 | 0.066* | |
| C18 | 0.6607 (6) | 0.6793 (4) | −0.2285 (2) | 0.0632 (13) | |
| H18 | 0.6950 | 0.6262 | −0.2624 | 0.076* | |
| C19 | 0.6194 (6) | 0.7971 (4) | −0.2443 (2) | 0.0664 (14) | |
| H19 | 0.6252 | 0.8235 | −0.2890 | 0.080* | |
| C20 | 0.5702 (6) | 0.8749 (4) | −0.1946 (2) | 0.0565 (12) | |
| H20 | 0.5415 | 0.9543 | −0.2053 | 0.068* | |
| C21 | 0.5628 (5) | 0.8365 (3) | −0.1283 (2) | 0.0511 (11) | |
| H21 | 0.5301 | 0.8907 | −0.0947 | 0.061* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.062 (3) | 0.0403 (18) | 0.038 (2) | −0.0013 (18) | −0.0013 (18) | 0.0009 (16) |
| N2 | 0.053 (2) | 0.0448 (18) | 0.0352 (18) | 0.0040 (18) | 0.0059 (17) | 0.0001 (15) |
| O1 | 0.066 (2) | 0.0506 (16) | 0.0487 (17) | −0.0063 (15) | −0.0034 (16) | 0.0039 (15) |
| O2 | 0.0445 (17) | 0.0555 (16) | 0.0642 (18) | −0.0006 (14) | 0.0037 (16) | 0.0091 (14) |
| C1 | 0.040 (2) | 0.045 (3) | 0.047 (3) | 0.007 (2) | 0.001 (2) | 0.001 (2) |
| C2 | 0.040 (3) | 0.050 (2) | 0.037 (2) | 0.001 (2) | 0.000 (2) | 0.005 (2) |
| C3 | 0.064 (3) | 0.050 (3) | 0.048 (3) | −0.004 (2) | −0.004 (2) | 0.000 (2) |
| C4 | 0.074 (4) | 0.064 (3) | 0.052 (3) | −0.009 (3) | −0.001 (3) | 0.015 (3) |
| C5 | 0.073 (4) | 0.072 (3) | 0.047 (3) | 0.005 (3) | −0.001 (3) | 0.012 (3) |
| C6 | 0.090 (4) | 0.064 (3) | 0.045 (3) | 0.000 (3) | −0.003 (3) | −0.005 (2) |
| C7 | 0.060 (3) | 0.054 (3) | 0.050 (3) | −0.002 (2) | −0.005 (2) | 0.000 (2) |
| C8 | 0.046 (3) | 0.039 (2) | 0.040 (2) | 0.003 (2) | −0.001 (2) | −0.002 (2) |
| C9 | 0.043 (2) | 0.047 (2) | 0.043 (2) | −0.005 (2) | −0.002 (2) | 0.000 (2) |
| C10 | 0.043 (2) | 0.041 (2) | 0.037 (2) | −0.0017 (19) | −0.006 (2) | −0.004 (2) |
| C11 | 0.051 (3) | 0.045 (2) | 0.057 (3) | −0.003 (2) | 0.000 (3) | −0.002 (2) |
| C12 | 0.056 (3) | 0.059 (3) | 0.080 (3) | 0.002 (3) | −0.012 (3) | −0.012 (3) |
| C13 | 0.067 (4) | 0.063 (3) | 0.078 (3) | 0.015 (3) | −0.029 (3) | −0.003 (3) |
| C14 | 0.080 (4) | 0.079 (4) | 0.075 (3) | 0.006 (3) | −0.013 (3) | 0.028 (3) |
| C15 | 0.059 (3) | 0.070 (3) | 0.057 (3) | 0.001 (3) | −0.002 (3) | 0.018 (3) |
| C16 | 0.042 (3) | 0.043 (2) | 0.040 (2) | −0.001 (2) | 0.004 (2) | 0.000 (2) |
| C17 | 0.064 (3) | 0.051 (2) | 0.049 (2) | 0.004 (3) | 0.002 (2) | −0.002 (2) |
| C18 | 0.075 (3) | 0.067 (3) | 0.047 (3) | −0.014 (3) | 0.007 (3) | −0.005 (3) |
| C19 | 0.070 (3) | 0.084 (4) | 0.045 (3) | −0.015 (3) | 0.000 (3) | 0.008 (3) |
| C20 | 0.064 (3) | 0.056 (3) | 0.049 (3) | −0.006 (3) | 0.002 (2) | 0.015 (2) |
| C21 | 0.057 (3) | 0.049 (3) | 0.047 (3) | −0.003 (2) | 0.004 (2) | −0.003 (2) |
| N1—C1 | 1.366 (4) | C10—C11 | 1.380 (5) |
| N1—N2 | 1.373 (4) | C10—C15 | 1.383 (5) |
| N1—H1 | 0.8600 | C11—C12 | 1.392 (5) |
| N2—C8 | 1.288 (4) | C11—H11 | 0.9300 |
| O1—C1 | 1.226 (4) | C12—C13 | 1.372 (6) |
| O2—C9 | 1.439 (4) | C12—H12 | 0.9300 |
| O2—H2 | 0.8200 | C13—C14 | 1.365 (7) |
| C1—C2 | 1.485 (5) | C13—H13 | 0.9300 |
| C2—C7 | 1.365 (5) | C14—C15 | 1.379 (6) |
| C2—C3 | 1.381 (5) | C14—H14 | 0.9300 |
| C3—C4 | 1.380 (5) | C15—H15 | 0.9300 |
| C3—H3 | 0.9300 | C16—C17 | 1.379 (5) |
| C4—C5 | 1.366 (5) | C16—C21 | 1.383 (5) |
| C4—H4 | 0.9300 | C17—C18 | 1.389 (5) |
| C5—C6 | 1.366 (6) | C17—H17 | 0.9300 |
| C5—H5 | 0.9300 | C18—C19 | 1.378 (6) |
| C6—C7 | 1.378 (5) | C18—H18 | 0.9300 |
| C6—H6 | 0.9300 | C19—C20 | 1.359 (5) |
| C7—H7 | 0.9300 | C19—H19 | 0.9300 |
| C8—C16 | 1.477 (5) | C20—C21 | 1.375 (5) |
| C8—C9 | 1.524 (5) | C20—H20 | 0.9300 |
| C9—C10 | 1.507 (5) | C21—H21 | 0.9300 |
| C9—H9 | 0.9800 | ||
| C1—N1—N2 | 118.1 (3) | C11—C10—C9 | 121.7 (3) |
| C1—N1—H1 | 121.0 | C15—C10—C9 | 120.1 (4) |
| N2—N1—H1 | 121.0 | C10—C11—C12 | 121.1 (4) |
| C8—N2—N1 | 116.9 (3) | C10—C11—H11 | 119.4 |
| C9—O2—H2 | 109.5 | C12—C11—H11 | 119.4 |
| O1—C1—N1 | 121.4 (4) | C13—C12—C11 | 119.4 (4) |
| O1—C1—C2 | 121.8 (4) | C13—C12—H12 | 120.3 |
| N1—C1—C2 | 116.8 (4) | C11—C12—H12 | 120.3 |
| C7—C2—C3 | 118.4 (4) | C14—C13—C12 | 120.1 (4) |
| C7—C2—C1 | 117.0 (3) | C14—C13—H13 | 120.0 |
| C3—C2—C1 | 124.5 (4) | C12—C13—H13 | 120.0 |
| C4—C3—C2 | 120.4 (4) | C13—C14—C15 | 120.4 (4) |
| C4—C3—H3 | 119.8 | C13—C14—H14 | 119.8 |
| C2—C3—H3 | 119.8 | C15—C14—H14 | 119.8 |
| C5—C4—C3 | 120.3 (4) | C14—C15—C10 | 120.9 (4) |
| C5—C4—H4 | 119.8 | C14—C15—H15 | 119.6 |
| C3—C4—H4 | 119.8 | C10—C15—H15 | 119.6 |
| C4—C5—C6 | 119.5 (4) | C17—C16—C21 | 118.1 (4) |
| C4—C5—H5 | 120.3 | C17—C16—C8 | 121.8 (3) |
| C6—C5—H5 | 120.3 | C21—C16—C8 | 120.1 (3) |
| C5—C6—C7 | 120.2 (4) | C16—C17—C18 | 120.7 (4) |
| C5—C6—H6 | 119.9 | C16—C17—H17 | 119.7 |
| C7—C6—H6 | 119.9 | C18—C17—H17 | 119.7 |
| C2—C7—C6 | 121.1 (4) | C19—C18—C17 | 119.7 (4) |
| C2—C7—H7 | 119.5 | C19—C18—H18 | 120.1 |
| C6—C7—H7 | 119.5 | C17—C18—H18 | 120.1 |
| N2—C8—C16 | 115.9 (3) | C20—C19—C18 | 120.1 (4) |
| N2—C8—C9 | 124.4 (3) | C20—C19—H19 | 120.0 |
| C16—C8—C9 | 119.6 (3) | C18—C19—H19 | 120.0 |
| O2—C9—C10 | 107.7 (3) | C19—C20—C21 | 120.1 (4) |
| O2—C9—C8 | 110.5 (3) | C19—C20—H20 | 120.0 |
| C10—C9—C8 | 113.5 (3) | C21—C20—H20 | 120.0 |
| O2—C9—H9 | 108.4 | C20—C21—C16 | 121.3 (4) |
| C10—C9—H9 | 108.4 | C20—C21—H21 | 119.3 |
| C8—C9—H9 | 108.4 | C16—C21—H21 | 119.3 |
| C11—C10—C15 | 118.1 (4) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···O1i | 0.82 | 2.45 | 2.998 (4) | 125 |
| O2—H2···N2i | 0.82 | 2.20 | 2.992 (4) | 164 |
| N1—H1···O2 | 0.86 | 2.12 | 2.715 (4) | 126 |
| Symmetry codes: (i) x−1/2, −y+3/2, −z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H2···O1i | 0.82 | 2.45 | 2.998 (4) | 125 |
| O2—H2···N2i | 0.82 | 2.20 | 2.992 (4) | 164 |
| N1—H1···O2 | 0.86 | 2.12 | 2.715 (4) | 126 |
| Symmetry codes: (i) x−1/2, −y+3/2, −z. |
The authors acknowledge financial support by the Foundation of Binzhou University (grant No. BZXYQNLG2005013).
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Schiff bases and their metal complexes were reported to exhibit fungicidal, bactericidal, antiviral, and antitubercular activity (Chakraborty et al., 1996; Jeewoth et al., 1999). Herewith we present the title compound (I), which is a new Shiff base compound.
In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in similar compounds (Nie et al., 2008; Fun et al., 2008) The C=N (C8=N2) bond length in the molecule is 1.287 (3) Å. Two benzene rings - C2—C7 and C16—C21, respectively - form a dihedral angle of 37.94 (7) °. The amino group is involved in formation of intramolecular N—H···O hydrogen bond (Table 1), while intermolecular O—H···N and O—H···O hydrogen bonds (Table 1) link the molecules into chains running in direction [100].