Acta Cryst. (2011). E67, o880 [ doi:10.1107/S1600536811008932 ]
The molecule of the title Schiff base compound, C15H14N2O5, was obtained from a condensation reaction of 4-acetoxy-3-methoxybenzaldehyde and 2-furylcarbonylhydrazide. In the molecule, the furyl ring makes a dihedral angle of 14.63 (10)° with the benzene ring. In the crystal, intermolecular N-H
O hydrogen bonds link the molecules into chains along the b axis. Futhermore, weak C-HO interactions connect the chains, forming corrugated layers parallel to (001). The dihedral angle between the rings is 14.63 (10)°.
Furan-2-carbohydrazine (1 mmol, 0.126 g) was dissolved in anhydrous ethanol (10 ml), The mixture was stirred for several minitutes at 351k, 4-acetoxy-3-methoxybenzaldehyde (1 mmol, 0.194 g) in ethanol (10 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 3 h. The product was isolated and recrystallized from DMF, single crystals of (I) was obtained after one month.
All H atoms were positioned geometrically and refined as riding with C—H=0.93 (aromatic), 0.97(methylene), 0.96 Å(methyl) and N—H=0.86 Å, with Uiso(H)=1.2Ueq(CH, CH2 or NH) and Uiso(H)=1.5Ueq(C).
In the absence of significant anomalous scattering, the absolute structure could not be reliably determined and then any references to the Flack parameter were removed.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./dn2664fig1thm.gif)
| Fig. 1. Molecular view of (I) with the atom labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. |
![[Figure 2]](./dn2664fig2thm.gif)
| Fig. 2. Packing view of (I) projected down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity. |
| C15H14N2O5 | F(000) = 632 |
| Mr = 302.28 | Dx = 1.387 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 2890 reflections |
| a = 4.9987 (2) Å | θ = 2.8–25.0° |
| b = 13.4200 (5) Å | µ = 0.11 mm−1 |
| c = 21.5876 (8) Å | T = 296 K |
| V = 1448.15 (10) Å3 | Block, colorless |
| Z = 4 | 0.21 × 0.19 × 0.18 mm |
| Bruker SMART CCD area-detector diffractometer | 3626 independent reflections |
| Radiation source: fine-focus sealed tube | 2988 reflections with I > 2σ(I) |
| graphite | Rint = 0.037 |
| ω scans | θmax = 28.4°, θmin = 1.8° |
| Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −6→6 |
| Tmin = 0.973, Tmax = 0.977 | k = −17→17 |
| 39211 measured reflections | l = −28→28 |
| 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)] = 0.037 | H-atom parameters constrained |
| wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.1124P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max = 0.001 |
| 3626 reflections | Δρmax = 0.17 e Å−3 |
| 200 parameters | Δρmin = −0.12 e Å−3 |
| 0 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (2) |
| C15H14N2O5 | V = 1448.15 (10) Å3 |
| Mr = 302.28 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 4.9987 (2) Å | µ = 0.11 mm−1 |
| b = 13.4200 (5) Å | T = 296 K |
| c = 21.5876 (8) Å | 0.21 × 0.19 × 0.18 mm |
| Bruker SMART CCD area-detector diffractometer | 3626 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2988 reflections with I > 2σ(I) |
| Tmin = 0.973, Tmax = 0.977 | Rint = 0.037 |
| 39211 measured reflections | θmax = 28.4° |
| R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
| wR(F2) = 0.105 | Δρmax = 0.17 e Å−3 |
| S = 1.04 | Δρmin = −0.12 e Å−3 |
| 3626 reflections | Absolute structure: ? |
| 200 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 | ||
| N2 | 0.1299 (3) | 0.82093 (8) | 0.14030 (6) | 0.0421 (3) | |
| N1 | 0.1018 (3) | 0.91747 (9) | 0.16153 (6) | 0.0457 (3) | |
| H1A | −0.0498 | 0.9473 | 0.1583 | 0.055* | |
| O4 | −0.0888 (3) | 0.40544 (8) | 0.00497 (5) | 0.0589 (3) | |
| O1 | 0.4391 (3) | 1.11568 (9) | 0.23940 (6) | 0.0614 (3) | |
| O3 | 0.2649 (3) | 0.44319 (8) | 0.09449 (6) | 0.0607 (3) | |
| O2 | 0.5320 (2) | 0.92740 (9) | 0.19504 (6) | 0.0548 (3) | |
| C5 | 0.3114 (3) | 0.96497 (10) | 0.18735 (7) | 0.0399 (3) | |
| C9 | 0.1023 (4) | 0.51982 (10) | 0.07856 (7) | 0.0452 (3) | |
| C8 | 0.1028 (3) | 0.61391 (10) | 0.10565 (7) | 0.0433 (3) | |
| H8A | 0.2245 | 0.6285 | 0.1370 | 0.052* | |
| C6 | −0.0733 (3) | 0.78742 (11) | 0.11141 (7) | 0.0432 (3) | |
| H6A | −0.2222 | 0.8282 | 0.1063 | 0.052* | |
| C7 | −0.0777 (3) | 0.68616 (10) | 0.08613 (7) | 0.0420 (3) | |
| C10 | −0.0806 (4) | 0.50087 (11) | 0.03118 (7) | 0.0474 (4) | |
| C4 | 0.2508 (3) | 1.06823 (10) | 0.20534 (7) | 0.0428 (3) | |
| O5 | 0.2054 (4) | 0.45208 (11) | −0.06712 (7) | 0.0836 (5) | |
| C12 | −0.2646 (4) | 0.66377 (12) | 0.04072 (8) | 0.0505 (4) | |
| H12A | −0.3910 | 0.7111 | 0.0291 | 0.061* | |
| C11 | −0.2631 (4) | 0.57083 (12) | 0.01263 (7) | 0.0525 (4) | |
| H11A | −0.3851 | 0.5561 | −0.0186 | 0.063* | |
| C3 | 0.0474 (4) | 1.12983 (14) | 0.19440 (10) | 0.0670 (5) | |
| H3A | −0.1064 | 1.1157 | 0.1718 | 0.080* | |
| C14 | 0.0652 (4) | 0.38936 (12) | −0.04507 (8) | 0.0552 (4) | |
| C2 | 0.1111 (5) | 1.22134 (14) | 0.22389 (11) | 0.0748 (6) | |
| H2B | 0.0064 | 1.2786 | 0.2247 | 0.090* | |
| C15 | 0.0306 (6) | 0.28530 (14) | −0.06886 (9) | 0.0775 (6) | |
| H15A | 0.1423 | 0.2757 | −0.1045 | 0.116* | |
| H15B | −0.1531 | 0.2749 | −0.0801 | 0.116* | |
| H15C | 0.0803 | 0.2387 | −0.0372 | 0.116* | |
| C13 | 0.4284 (5) | 0.45684 (14) | 0.14794 (9) | 0.0655 (5) | |
| H13A | 0.5339 | 0.3981 | 0.1547 | 0.098* | |
| H13B | 0.3168 | 0.4687 | 0.1834 | 0.098* | |
| H13C | 0.5444 | 0.5129 | 0.1417 | 0.098* | |
| C1 | 0.3456 (5) | 1.20943 (13) | 0.24976 (9) | 0.0657 (5) | |
| H1B | 0.4358 | 1.2582 | 0.2721 | 0.079* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N2 | 0.0475 (7) | 0.0290 (5) | 0.0499 (6) | 0.0012 (5) | 0.0038 (5) | −0.0045 (5) |
| N1 | 0.0406 (6) | 0.0314 (6) | 0.0650 (8) | 0.0019 (5) | −0.0017 (6) | −0.0106 (6) |
| O4 | 0.0856 (9) | 0.0378 (6) | 0.0534 (6) | −0.0175 (6) | 0.0034 (6) | −0.0124 (5) |
| O1 | 0.0652 (8) | 0.0464 (6) | 0.0725 (8) | −0.0082 (6) | −0.0158 (7) | −0.0114 (6) |
| O3 | 0.0807 (8) | 0.0366 (5) | 0.0648 (7) | 0.0077 (6) | −0.0113 (7) | −0.0101 (5) |
| O2 | 0.0457 (6) | 0.0441 (6) | 0.0746 (8) | 0.0061 (5) | −0.0080 (6) | −0.0052 (5) |
| C5 | 0.0438 (8) | 0.0336 (7) | 0.0424 (7) | 0.0003 (6) | 0.0013 (6) | −0.0016 (5) |
| C9 | 0.0554 (9) | 0.0327 (7) | 0.0474 (8) | −0.0036 (6) | 0.0012 (7) | −0.0045 (6) |
| C8 | 0.0485 (8) | 0.0353 (7) | 0.0460 (7) | −0.0037 (6) | −0.0013 (6) | −0.0068 (6) |
| C6 | 0.0444 (7) | 0.0354 (7) | 0.0498 (8) | 0.0016 (6) | 0.0015 (7) | −0.0050 (6) |
| C7 | 0.0469 (8) | 0.0353 (7) | 0.0439 (7) | −0.0050 (6) | 0.0033 (6) | −0.0034 (6) |
| C10 | 0.0622 (10) | 0.0349 (7) | 0.0451 (8) | −0.0106 (7) | 0.0036 (7) | −0.0079 (6) |
| C4 | 0.0462 (8) | 0.0349 (7) | 0.0475 (8) | −0.0037 (6) | −0.0005 (6) | −0.0056 (6) |
| O5 | 0.1165 (13) | 0.0615 (8) | 0.0730 (9) | −0.0209 (9) | 0.0306 (9) | −0.0194 (7) |
| C12 | 0.0532 (9) | 0.0444 (8) | 0.0539 (9) | −0.0024 (7) | −0.0056 (7) | −0.0015 (7) |
| C11 | 0.0616 (10) | 0.0474 (8) | 0.0483 (8) | −0.0122 (8) | −0.0087 (7) | −0.0041 (7) |
| C3 | 0.0597 (10) | 0.0470 (9) | 0.0944 (14) | 0.0113 (8) | −0.0142 (11) | −0.0217 (9) |
| C14 | 0.0775 (11) | 0.0424 (8) | 0.0457 (8) | −0.0024 (8) | −0.0066 (8) | −0.0082 (7) |
| C2 | 0.0847 (15) | 0.0432 (9) | 0.0965 (15) | 0.0123 (10) | 0.0050 (13) | −0.0206 (10) |
| C15 | 0.1201 (18) | 0.0464 (9) | 0.0660 (11) | −0.0009 (11) | −0.0085 (12) | −0.0196 (9) |
| C13 | 0.0848 (13) | 0.0467 (9) | 0.0648 (11) | 0.0133 (9) | −0.0169 (10) | −0.0028 (8) |
| C1 | 0.0883 (14) | 0.0406 (9) | 0.0682 (11) | −0.0136 (9) | 0.0057 (11) | −0.0161 (8) |
| N2—C6 | 1.2742 (19) | C10—C11 | 1.369 (3) |
| N2—N1 | 1.3814 (16) | C4—C3 | 1.331 (2) |
| N1—C5 | 1.3471 (19) | O5—C14 | 1.194 (2) |
| N1—H1A | 0.8600 | C12—C11 | 1.387 (2) |
| O4—C14 | 1.344 (2) | C12—H12A | 0.9300 |
| O4—C10 | 1.4007 (17) | C11—H11A | 0.9300 |
| O1—C4 | 1.3537 (18) | C3—C2 | 1.419 (3) |
| O1—C1 | 1.361 (2) | C3—H3A | 0.9300 |
| O3—C9 | 1.355 (2) | C14—C15 | 1.498 (2) |
| O3—C13 | 1.426 (2) | C2—C1 | 1.308 (3) |
| O2—C5 | 1.2242 (18) | C2—H2B | 0.9300 |
| C5—C4 | 1.4706 (19) | C15—H15A | 0.9600 |
| C9—C8 | 1.3915 (19) | C15—H15B | 0.9600 |
| C9—C10 | 1.395 (2) | C15—H15C | 0.9600 |
| C8—C7 | 1.390 (2) | C13—H13A | 0.9600 |
| C8—H8A | 0.9300 | C13—H13B | 0.9600 |
| C6—C7 | 1.4644 (19) | C13—H13C | 0.9600 |
| C6—H6A | 0.9300 | C1—H1B | 0.9300 |
| C7—C12 | 1.387 (2) | ||
| C6—N2—N1 | 114.35 (12) | C11—C12—H12A | 120.0 |
| C5—N1—N2 | 120.13 (12) | C7—C12—H12A | 120.0 |
| C5—N1—H1A | 119.9 | C10—C11—C12 | 119.52 (15) |
| N2—N1—H1A | 119.9 | C10—C11—H11A | 120.2 |
| C14—O4—C10 | 117.05 (13) | C12—C11—H11A | 120.2 |
| C4—O1—C1 | 106.58 (15) | C4—C3—C2 | 106.64 (17) |
| C9—O3—C13 | 116.85 (12) | C4—C3—H3A | 126.7 |
| O2—C5—N1 | 124.19 (13) | C2—C3—H3A | 126.7 |
| O2—C5—C4 | 122.54 (14) | O5—C14—O4 | 122.91 (15) |
| N1—C5—C4 | 113.27 (13) | O5—C14—C15 | 126.03 (19) |
| O3—C9—C8 | 125.51 (15) | O4—C14—C15 | 111.05 (17) |
| O3—C9—C10 | 116.14 (13) | C1—C2—C3 | 106.66 (18) |
| C8—C9—C10 | 118.34 (15) | C1—C2—H2B | 126.7 |
| C7—C8—C9 | 120.29 (15) | C3—C2—H2B | 126.7 |
| C7—C8—H8A | 119.9 | C14—C15—H15A | 109.5 |
| C9—C8—H8A | 119.9 | C14—C15—H15B | 109.5 |
| N2—C6—C7 | 121.46 (14) | H15A—C15—H15B | 109.5 |
| N2—C6—H6A | 119.3 | C14—C15—H15C | 109.5 |
| C7—C6—H6A | 119.3 | H15A—C15—H15C | 109.5 |
| C12—C7—C8 | 120.03 (13) | H15B—C15—H15C | 109.5 |
| C12—C7—C6 | 118.33 (14) | O3—C13—H13A | 109.5 |
| C8—C7—C6 | 121.63 (14) | O3—C13—H13B | 109.5 |
| C11—C10—C9 | 121.73 (13) | H13A—C13—H13B | 109.5 |
| C11—C10—O4 | 119.31 (15) | O3—C13—H13C | 109.5 |
| C9—C10—O4 | 118.82 (15) | H13A—C13—H13C | 109.5 |
| C3—C4—O1 | 109.59 (13) | H13B—C13—H13C | 109.5 |
| C3—C4—C5 | 134.06 (15) | C2—C1—O1 | 110.52 (17) |
| O1—C4—C5 | 116.33 (13) | C2—C1—H1B | 124.7 |
| C11—C12—C7 | 120.00 (16) | O1—C1—H1B | 124.7 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O2i | 0.86 | 2.25 | 2.9414 (18) | 137 |
| C1—H1B···O2ii | 0.93 | 2.38 | 3.217 (2) | 149 |
| Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O2i | 0.86 | 2.25 | 2.9414 (18) | 137 |
| C1—H1B···O2ii | 0.93 | 2.38 | 3.217 (2) | 149 |
| Symmetry codes: (i) x−1, y, z; (ii) −x+1, y+1/2, −z+1/2. |
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Several phenylhydrazone derivatives have been shown to be potentially DNA-damaging and are mutagenic agents (Okabe et al. 1993). As part of our ongoing studies of Schiff bases, in this paper, we have synthesized the title compound and report the crystal structure.
The molecule adopts an E geometry with respect to the C=N bond (Fig. 1). The molecule is not planar, the dihedral angle between the furyl ring and the benzene ring is 14.63 (10)°, Bond lengths and bond angles agree with those of other hydrazone derivatives (Ohba, 1996; Baughman et al., 2004; Yao & Jing et al., 2007; Bakir & Gyles, 2003)
In the Crystal, Intermolecular N—H···O hydrogen bond link the molecules to form chains along the b axis. The chains are further connected to form corrugated layers parallel to the (0 0 1) plane (Table 1, Fig. 2).