Acta Cryst. (2009). E65, o2107 [ doi:10.1107/S1600536809030621 ]
The title compound, C15H14N2O3, was synthesized by the reaction of 4-methoxybenzaldehyde with 4-hydroxybenzohydrazide in methanol. The molecule adopts an E configuration about the C=N bond. The two benzene rings make a dihedral angle of 46.6 (2)°. In the crystal structure, molecules are linked into a two-dimensional network parallel to (001) through O-H
O and N-HO hydrogen bonds.
4-Methoxybenzaldehyde (13.6 mg, 0.1 mmol) and 4-hydroxybenzohydrazide (15.2 mg, 0.1 mmol) were mixed and refluxed in a methanol solution. After 30 min, the clear solution was evaporated to give colourless crystallites, which were recrystallized from methanol to form single crystals.
Atom H2A was located in a difference Fourier map and refined isotropically, with the N-H distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions [O-H = 0.82 Å and C-H = 0.93–0.96 Å] and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and C7).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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]](./ci2875fig1thm.gif)
| Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./ci2875fig2thm.gif)
| Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines. |
| C15H14N2O3 | F(000) = 1136 |
| Mr = 270.28 | Dx = 1.351 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 2853 reflections |
| a = 11.947 (2) Å | θ = 2.6–25.0° |
| b = 7.555 (1) Å | µ = 0.10 mm−1 |
| c = 29.452 (2) Å | T = 298 K |
| V = 2658.3 (6) Å3 | Block, colourless |
| Z = 8 | 0.20 × 0.20 × 0.17 mm |
| Bruker SMART CCD area-detector diffractometer | 2897 independent reflections |
| Radiation source: fine-focus sealed tube | 2030 reflections with I > 2σ(I) |
| graphite | Rint = 0.035 |
| ω scans | θmax = 27.0°, θmin = 1.4° |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −13→15 |
| Tmin = 0.981, Tmax = 0.984 | k = −9→9 |
| 15205 measured reflections | l = −33→37 |
| 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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0418P)2 + 0.5702P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max = 0.001 |
| 2897 reflections | Δρmax = 0.18 e Å−3 |
| 187 parameters | Δρmin = −0.15 e Å−3 |
| 1 restraint | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0025 (7) |
| C15H14N2O3 | V = 2658.3 (6) Å3 |
| Mr = 270.28 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 11.947 (2) Å | µ = 0.10 mm−1 |
| b = 7.555 (1) Å | T = 298 K |
| c = 29.452 (2) Å | 0.20 × 0.20 × 0.17 mm |
| Bruker SMART CCD area-detector diffractometer | 2897 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2030 reflections with I > 2σ(I) |
| Tmin = 0.981, Tmax = 0.984 | Rint = 0.035 |
| 15205 measured reflections | θmax = 27.0° |
| R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.103 | Δρmax = 0.18 e Å−3 |
| S = 1.04 | Δρmin = −0.15 e Å−3 |
| 2897 reflections | Absolute structure: ? |
| 187 parameters | Flack parameter: ? |
| 1 restraint | 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 | 0.77001 (10) | 0.20495 (17) | 0.58903 (4) | 0.0428 (3) | |
| N2 | 0.75665 (11) | 0.28526 (17) | 0.63096 (4) | 0.0427 (3) | |
| O1 | 0.93859 (13) | 0.00418 (19) | 0.39100 (4) | 0.0755 (4) | |
| O2 | 0.60541 (8) | 0.11510 (14) | 0.64634 (3) | 0.0460 (3) | |
| O3 | 0.61014 (9) | 0.54911 (17) | 0.82831 (3) | 0.0535 (3) | |
| H3 | 0.5439 | 0.5709 | 0.8329 | 0.080* | |
| C1 | 0.86784 (12) | 0.2014 (2) | 0.51899 (5) | 0.0407 (4) | |
| C2 | 0.79314 (13) | 0.0874 (2) | 0.49804 (5) | 0.0487 (4) | |
| H2 | 0.7279 | 0.0556 | 0.5132 | 0.058* | |
| C3 | 0.81269 (14) | 0.0203 (2) | 0.45558 (5) | 0.0535 (4) | |
| H3A | 0.7616 | −0.0568 | 0.4423 | 0.064* | |
| C4 | 0.90936 (15) | 0.0683 (2) | 0.43253 (5) | 0.0518 (4) | |
| C5 | 0.98315 (15) | 0.1872 (2) | 0.45215 (6) | 0.0567 (5) | |
| H5 | 1.0465 | 0.2232 | 0.4363 | 0.068* | |
| C6 | 0.96304 (14) | 0.2522 (2) | 0.49499 (6) | 0.0498 (4) | |
| H6 | 1.0135 | 0.3308 | 0.5081 | 0.060* | |
| C7 | 0.8819 (2) | −0.1482 (3) | 0.37488 (7) | 0.0800 (6) | |
| H7A | 0.8849 | −0.2396 | 0.3975 | 0.120* | |
| H7B | 0.9171 | −0.1893 | 0.3476 | 0.120* | |
| H7C | 0.8052 | −0.1190 | 0.3687 | 0.120* | |
| C8 | 0.84886 (12) | 0.2682 (2) | 0.56475 (5) | 0.0426 (4) | |
| H8 | 0.8944 | 0.3574 | 0.5763 | 0.051* | |
| C9 | 0.67022 (11) | 0.23670 (19) | 0.65719 (5) | 0.0363 (3) | |
| C10 | 0.65784 (11) | 0.33283 (19) | 0.70077 (5) | 0.0359 (3) | |
| C11 | 0.74372 (12) | 0.3390 (2) | 0.73227 (5) | 0.0418 (4) | |
| H11 | 0.8139 | 0.2948 | 0.7247 | 0.050* | |
| C12 | 0.72609 (12) | 0.4102 (2) | 0.77481 (5) | 0.0460 (4) | |
| H12 | 0.7839 | 0.4114 | 0.7960 | 0.055* | |
| C13 | 0.62246 (12) | 0.4800 (2) | 0.78614 (5) | 0.0391 (4) | |
| C14 | 0.53678 (12) | 0.4772 (2) | 0.75443 (5) | 0.0414 (4) | |
| H14 | 0.4675 | 0.5261 | 0.7615 | 0.050* | |
| C15 | 0.55430 (12) | 0.4021 (2) | 0.71250 (5) | 0.0422 (4) | |
| H15 | 0.4958 | 0.3977 | 0.6917 | 0.051* | |
| H2A | 0.8008 (14) | 0.3787 (19) | 0.6374 (6) | 0.080* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0453 (7) | 0.0455 (8) | 0.0375 (7) | −0.0003 (6) | 0.0089 (6) | −0.0040 (6) |
| N2 | 0.0450 (7) | 0.0437 (7) | 0.0393 (7) | −0.0044 (6) | 0.0098 (6) | −0.0066 (6) |
| O1 | 0.1010 (11) | 0.0751 (10) | 0.0503 (8) | −0.0109 (8) | 0.0234 (7) | −0.0152 (6) |
| O2 | 0.0436 (6) | 0.0499 (7) | 0.0447 (6) | −0.0074 (5) | 0.0081 (5) | −0.0078 (5) |
| O3 | 0.0464 (6) | 0.0737 (8) | 0.0404 (6) | 0.0078 (6) | 0.0045 (5) | −0.0117 (5) |
| C1 | 0.0425 (8) | 0.0401 (8) | 0.0396 (8) | 0.0018 (7) | 0.0081 (6) | 0.0033 (6) |
| C2 | 0.0471 (9) | 0.0513 (10) | 0.0478 (9) | −0.0039 (8) | 0.0096 (7) | 0.0015 (7) |
| C3 | 0.0601 (11) | 0.0542 (10) | 0.0464 (9) | −0.0064 (8) | 0.0015 (8) | −0.0035 (8) |
| C4 | 0.0642 (11) | 0.0501 (10) | 0.0412 (9) | 0.0023 (9) | 0.0109 (8) | 0.0001 (7) |
| C5 | 0.0597 (10) | 0.0585 (11) | 0.0519 (10) | −0.0062 (9) | 0.0217 (8) | −0.0006 (8) |
| C6 | 0.0501 (9) | 0.0482 (9) | 0.0512 (9) | −0.0069 (8) | 0.0115 (7) | −0.0013 (7) |
| C7 | 0.1133 (17) | 0.0747 (14) | 0.0520 (11) | −0.0059 (14) | 0.0008 (11) | −0.0156 (10) |
| C8 | 0.0411 (8) | 0.0418 (9) | 0.0449 (8) | −0.0003 (7) | 0.0058 (7) | 0.0002 (7) |
| C9 | 0.0356 (7) | 0.0365 (8) | 0.0369 (8) | 0.0022 (6) | 0.0015 (6) | 0.0018 (6) |
| C10 | 0.0359 (7) | 0.0355 (8) | 0.0363 (7) | −0.0006 (6) | 0.0051 (6) | 0.0011 (6) |
| C11 | 0.0320 (7) | 0.0495 (9) | 0.0438 (8) | 0.0056 (7) | 0.0050 (6) | −0.0003 (7) |
| C12 | 0.0364 (8) | 0.0616 (11) | 0.0401 (8) | 0.0057 (7) | −0.0030 (6) | −0.0039 (7) |
| C13 | 0.0401 (8) | 0.0411 (8) | 0.0360 (8) | 0.0000 (7) | 0.0059 (6) | 0.0005 (6) |
| C14 | 0.0319 (7) | 0.0442 (9) | 0.0480 (9) | 0.0034 (6) | 0.0056 (6) | −0.0051 (7) |
| C15 | 0.0339 (8) | 0.0477 (9) | 0.0449 (8) | 0.0021 (7) | −0.0019 (6) | −0.0039 (7) |
| N1—C8 | 1.2758 (18) | C5—H5 | 0.93 |
| N1—N2 | 1.3850 (16) | C6—H6 | 0.93 |
| N2—C9 | 1.3408 (18) | C7—H7A | 0.96 |
| N2—H2A | 0.901 (9) | C7—H7B | 0.96 |
| O1—C4 | 1.3610 (19) | C7—H7C | 0.96 |
| O1—C7 | 1.418 (2) | C8—H8 | 0.93 |
| O2—C9 | 1.2431 (17) | C9—C10 | 1.4822 (19) |
| O3—C13 | 1.3554 (17) | C10—C11 | 1.3841 (19) |
| O3—H3 | 0.82 | C10—C15 | 1.3868 (19) |
| C1—C2 | 1.385 (2) | C11—C12 | 1.3797 (19) |
| C1—C6 | 1.393 (2) | C11—H11 | 0.93 |
| C1—C8 | 1.457 (2) | C12—C13 | 1.386 (2) |
| C2—C3 | 1.370 (2) | C12—H12 | 0.93 |
| C2—H2 | 0.93 | C13—C14 | 1.386 (2) |
| C3—C4 | 1.388 (2) | C14—C15 | 1.375 (2) |
| C3—H3A | 0.93 | C14—H14 | 0.93 |
| C4—C5 | 1.385 (2) | C15—H15 | 0.93 |
| C5—C6 | 1.375 (2) | ||
| C8—N1—N2 | 114.89 (13) | O1—C7—H7C | 109.5 |
| C9—N2—N1 | 118.86 (13) | H7A—C7—H7C | 109.5 |
| C9—N2—H2A | 123.0 (12) | H7B—C7—H7C | 109.5 |
| N1—N2—H2A | 117.5 (12) | N1—C8—C1 | 120.25 (14) |
| C4—O1—C7 | 117.85 (15) | N1—C8—H8 | 119.9 |
| C13—O3—H3 | 109.5 | C1—C8—H8 | 119.9 |
| C2—C1—C6 | 118.11 (14) | O2—C9—N2 | 122.26 (13) |
| C2—C1—C8 | 121.81 (13) | O2—C9—C10 | 121.50 (12) |
| C6—C1—C8 | 120.08 (14) | N2—C9—C10 | 116.22 (13) |
| C3—C2—C1 | 121.80 (15) | C11—C10—C15 | 118.78 (13) |
| C3—C2—H2 | 119.1 | C11—C10—C9 | 121.54 (12) |
| C1—C2—H2 | 119.1 | C15—C10—C9 | 119.31 (13) |
| C2—C3—C4 | 119.46 (16) | C12—C11—C10 | 120.58 (13) |
| C2—C3—H3A | 120.3 | C12—C11—H11 | 119.7 |
| C4—C3—H3A | 120.3 | C10—C11—H11 | 119.7 |
| O1—C4—C5 | 116.26 (15) | C11—C12—C13 | 120.21 (13) |
| O1—C4—C3 | 124.07 (16) | C11—C12—H12 | 119.9 |
| C5—C4—C3 | 119.67 (15) | C13—C12—H12 | 119.9 |
| C6—C5—C4 | 120.22 (15) | O3—C13—C14 | 122.91 (13) |
| C6—C5—H5 | 119.9 | O3—C13—C12 | 117.64 (13) |
| C4—C5—H5 | 119.9 | C14—C13—C12 | 119.44 (13) |
| C5—C6—C1 | 120.67 (16) | C15—C14—C13 | 119.94 (13) |
| C5—C6—H6 | 119.7 | C15—C14—H14 | 120.0 |
| C1—C6—H6 | 119.7 | C13—C14—H14 | 120.0 |
| O1—C7—H7A | 109.5 | C14—C15—C10 | 121.01 (13) |
| O1—C7—H7B | 109.5 | C14—C15—H15 | 119.5 |
| H7A—C7—H7B | 109.5 | C10—C15—H15 | 119.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O2i | 0.82 | 1.91 | 2.7271 (15) | 171 |
| N2—H2A···O2ii | 0.90 (1) | 2.12 (1) | 3.0216 (17) | 173 (2) |
| Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, y+1/2, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O3—H3···O2i | 0.82 | 1.91 | 2.7271 (15) | 171 |
| N2—H2A···O2ii | 0.90 (1) | 2.12 (1) | 3.0216 (17) | 173 (2) |
| Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+3/2, y+1/2, z. |
Abdul Alhadi, A. A., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o908.
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.
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cao, G.-B. & Lu, X.-H. (2009). Acta Cryst. E65, o1600.
Cukurovali, A., Yilmaz, I., Gur, S. & Kazaz, C. (2006). Eur. J. Med. Chem. 41, 201–207.
Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o189.
Qu, L.-Z. & Cao, G.-B. (2009). Acta Cryst. E65, o1705.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Hydrazone compounds are a kind of important materials in biological and medicinal chemistry. They have been widely investigated for their antibacterial activities (Cukurovali et al., 2006). Recently, a number of hydrazone compounds have been prepared and structurally characterized (Abdul Alhadi et al., 2009; Mohd Lair et al., 2009; Cao & Lu, 2009; Qu & Cao, 2009). In this paper, the author reports the crystal structure of the title hydrazone compound.
The molecule of the title compound adopts an E configuration about the C═N bond (Fig. 1). The two benzene rings make a dihedral angle of 46.56 (7)°. The C8/N1/N2/C9/O2 plane makes dihedral angles of 8.2 (1) and 54.5 (1)°, respectively, with the C1—C6 and C10—C15 benzene rings. All the bond lengths are normal (Allen et al., 1987).
In the crystal structure, molecules are linked through N—H···O and O—H···O hydrogen bonds (Table 1), forming a two-dimensional network parallel to the (001) [Fig. 2].