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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1466.
Published online 2009 June 6. doi:  10.1107/S1600536809020066
PMCID: PMC2969308

(E)-4-Hydr­oxy-N′-(4-nitro­benzyl­idene)benzohydrazide

Abstract

The mol­ecule of the title compound, C14H11N3O4, is approximately planar, the dihedral angle between the planes of the two substituted benzene rings being 2.54 (7)°. The mol­ecule exists in a trans configuration with respect to the central methyl­idene unit. In the crystal structure, mol­ecules are linked through inter­molecular O—H(...)O, N—H(...)O and C—H(...)O hydrogen bonds, forming layers parallel to (101). The O/N—H(...)O and C—H(...)O inter­actions form a pair of bifurcated acceptor bonds involving the cabon­yl/nitro O atom, generating an R 2 1(6) motif.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 [triangle]); Raj et al. (2007 [triangle]); Jimenez-Pulido et al. (2008 [triangle]). For related structures, see: Ban & Li (2008a [triangle],b [triangle]); Li & Ban (2009a [triangle],b [triangle]); Yehye et al. (2008 [triangle]); Fun et al. (2008a [triangle],b [triangle]); Yang et al. (2008 [triangle]); Ejsmont et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1466-scheme1.jpg

Experimental

Crystal data

  • C14H11N3O4
  • M r = 285.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1466-efi1.jpg
  • a = 7.659 (1) Å
  • b = 13.587 (2) Å
  • c = 12.561 (2) Å
  • β = 92.784 (5)°
  • V = 1305.6 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.20 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.979, T max = 0.981
  • 7862 measured reflections
  • 2835 independent reflections
  • 2109 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.111
  • S = 1.04
  • 2835 reflections
  • 195 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020066/ci2812sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020066/ci2812Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Schiff bases derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a great deal of Schiff bases have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported a few such compounds (Ban & Li, 2008a,b; Li & Ban, 2009a,b). We report here the crystal structure of the title new compound.

The title Schiff base molecule (Fig. 1) is nearly planar, with the dihedral angle between the two benzene rings being 2.54 (7)°. The molecule exists in a trans configuration with respect to the central methylidene (C7═N1) unit. The N2—N1—C7—C1 torsion angle is 179.12 (14)°.

In the crystal structure, the molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1), forming layers parallel to the (101) (Fig. 2). Within the layer, C—H···O hydrogen bonds are also observed.

Experimental

The title compound was prepared by refluxing 4-nitrobenzaldehyde (1.0 mol) with 4-hydroxybenzohydrazide (1.0 mol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. A colourless solid product was filtered, and washed three times with methanol. Colourless block-shaped crystals of the title compound were obtained from a methanol solution by slow evaporation in air.

Refinement

Atom H2B was located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1)Å and Uiso fixed at 0.08 Å2. The remaining H atoms were placed in calculated positions (C–H = 0.93 Å and O–H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
Fig. 2.
The packing diagram of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Crystal data

C14H11N3O4F(000) = 592
Mr = 285.26Dx = 1.451 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2390 reflections
a = 7.659 (1) Åθ = 3.0–30.5°
b = 13.587 (2) ŵ = 0.11 mm1
c = 12.561 (2) ÅT = 298 K
β = 92.784 (5)°Block, colourless
V = 1305.6 (3) Å30.20 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2835 independent reflections
Radiation source: fine-focus sealed tube2109 reflections with I > 2σ(I)
graphiteRint = 0.027
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.979, Tmax = 0.981k = −17→15
7862 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111w = 1/[σ2(Fo2) + (0.0467P)2 + 0.3196P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2835 reflectionsΔρmax = 0.21 e Å3
195 parametersΔρmin = −0.13 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0104 (15)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.20673 (17)0.97706 (9)1.04460 (10)0.0410 (3)
N20.26363 (19)1.05171 (9)0.98149 (10)0.0431 (3)
N30.0157 (2)0.54652 (10)1.21921 (11)0.0504 (4)
O10.18428 (15)1.16731 (8)1.09824 (8)0.0472 (3)
O20.51173 (18)1.44263 (8)0.75115 (9)0.0541 (3)
H20.55481.41940.69820.081*
O30.0321 (2)0.46801 (10)1.17422 (12)0.0883 (6)
O4−0.04623 (18)0.55386 (9)1.30667 (10)0.0611 (4)
C10.1672 (2)0.80400 (11)1.06387 (12)0.0391 (4)
C20.1011 (2)0.80979 (11)1.16524 (12)0.0423 (4)
H2A0.08980.87071.19800.051*
C30.0527 (2)0.72557 (12)1.21665 (12)0.0418 (4)
H30.00850.72881.28420.050*
C40.0707 (2)0.63608 (11)1.16619 (12)0.0402 (4)
C50.1366 (2)0.62796 (12)1.06648 (13)0.0455 (4)
H50.14830.56681.03440.055*
C60.1845 (2)0.71259 (12)1.01580 (12)0.0450 (4)
H60.22900.70870.94840.054*
C70.2198 (2)0.89103 (11)1.00586 (13)0.0439 (4)
H70.26420.88350.93870.053*
C80.25098 (19)1.14649 (11)1.01458 (11)0.0354 (3)
C90.32220 (19)1.22217 (11)0.94326 (11)0.0348 (3)
C100.3187 (2)1.32057 (11)0.97329 (12)0.0404 (4)
H100.27341.33781.03810.048*
C110.3812 (2)1.39297 (11)0.90850 (13)0.0447 (4)
H110.37721.45850.92980.054*
C120.4503 (2)1.36889 (11)0.81144 (12)0.0390 (4)
C130.4543 (2)1.27096 (11)0.78040 (12)0.0410 (4)
H130.49951.25380.71560.049*
C140.3915 (2)1.19946 (11)0.84559 (12)0.0403 (4)
H140.39521.13400.82400.048*
H2B0.303 (3)1.0358 (15)0.9176 (10)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0486 (8)0.0377 (7)0.0377 (7)−0.0014 (6)0.0127 (6)0.0081 (6)
N20.0616 (9)0.0335 (7)0.0359 (7)−0.0021 (6)0.0200 (6)0.0028 (5)
N30.0650 (10)0.0397 (8)0.0477 (8)−0.0055 (7)0.0146 (7)0.0081 (6)
O10.0630 (7)0.0441 (6)0.0364 (6)0.0005 (5)0.0217 (5)−0.0009 (5)
O20.0760 (9)0.0361 (6)0.0525 (7)−0.0056 (6)0.0280 (6)0.0047 (5)
O30.1579 (16)0.0359 (7)0.0749 (10)−0.0156 (9)0.0465 (10)−0.0013 (7)
O40.0814 (9)0.0505 (7)0.0537 (7)−0.0059 (6)0.0289 (7)0.0118 (6)
C10.0401 (8)0.0381 (8)0.0395 (8)−0.0015 (6)0.0068 (6)0.0070 (6)
C20.0511 (10)0.0350 (8)0.0413 (9)−0.0008 (7)0.0087 (7)0.0012 (6)
C30.0477 (9)0.0425 (9)0.0358 (8)0.0001 (7)0.0103 (7)0.0051 (7)
C40.0440 (9)0.0364 (8)0.0408 (8)−0.0029 (7)0.0073 (7)0.0076 (6)
C50.0563 (10)0.0368 (8)0.0446 (9)−0.0019 (7)0.0129 (8)0.0002 (7)
C60.0546 (10)0.0436 (9)0.0379 (8)−0.0008 (7)0.0141 (7)0.0029 (7)
C70.0526 (10)0.0418 (9)0.0384 (8)−0.0023 (7)0.0135 (7)0.0047 (7)
C80.0375 (8)0.0388 (8)0.0307 (7)0.0026 (6)0.0091 (6)0.0001 (6)
C90.0378 (8)0.0342 (7)0.0331 (7)0.0017 (6)0.0095 (6)−0.0003 (6)
C100.0495 (9)0.0379 (8)0.0352 (8)0.0012 (7)0.0158 (7)−0.0050 (6)
C110.0568 (10)0.0313 (8)0.0473 (9)−0.0003 (7)0.0161 (7)−0.0051 (7)
C120.0432 (9)0.0333 (7)0.0414 (8)−0.0014 (6)0.0111 (7)0.0027 (6)
C130.0516 (9)0.0385 (8)0.0345 (8)−0.0003 (7)0.0178 (7)−0.0022 (6)
C140.0529 (9)0.0302 (7)0.0394 (8)−0.0006 (6)0.0165 (7)−0.0034 (6)

Geometric parameters (Å, °)

N1—C71.272 (2)C4—C51.377 (2)
N1—N21.3714 (17)C5—C61.373 (2)
N2—C81.3581 (19)C5—H50.93
N2—H2B0.899 (9)C6—H60.93
N3—O31.2164 (18)C7—H70.93
N3—O41.2219 (17)C8—C91.4848 (19)
N3—C41.4590 (19)C9—C101.390 (2)
O1—C81.2237 (16)C9—C141.395 (2)
O2—C121.3539 (17)C10—C111.377 (2)
O2—H20.82C10—H100.93
C1—C61.390 (2)C11—C121.392 (2)
C1—C21.395 (2)C11—H110.93
C1—C71.456 (2)C12—C131.387 (2)
C2—C31.374 (2)C13—C141.373 (2)
C2—H2A0.93C13—H130.93
C3—C41.381 (2)C14—H140.93
C3—H30.93
C7—N1—N2115.18 (12)C1—C6—H6119.5
C8—N2—N1119.67 (12)N1—C7—C1121.73 (14)
C8—N2—H2B122.3 (14)N1—C7—H7119.1
N1—N2—H2B117.9 (14)C1—C7—H7119.1
O3—N3—O4122.86 (14)O1—C8—N2121.40 (13)
O3—N3—C4118.74 (14)O1—C8—C9122.61 (13)
O4—N3—C4118.40 (14)N2—C8—C9115.99 (12)
C12—O2—H2109.5C10—C9—C14117.70 (13)
C6—C1—C2119.55 (14)C10—C9—C8119.34 (13)
C6—C1—C7118.28 (14)C14—C9—C8122.96 (13)
C2—C1—C7122.18 (14)C11—C10—C9120.99 (14)
C3—C2—C1120.02 (14)C11—C10—H10119.5
C3—C2—H2A120.0C9—C10—H10119.5
C1—C2—H2A120.0C10—C11—C12120.51 (14)
C2—C3—C4118.84 (14)C10—C11—H11119.7
C2—C3—H3120.6C12—C11—H11119.7
C4—C3—H3120.6O2—C12—C13122.66 (13)
C5—C4—C3122.48 (14)O2—C12—C11118.25 (13)
C5—C4—N3118.35 (14)C13—C12—C11119.09 (14)
C3—C4—N3119.16 (13)C14—C13—C12119.87 (13)
C6—C5—C4118.20 (15)C14—C13—H13120.1
C6—C5—H5120.9C12—C13—H13120.1
C4—C5—H5120.9C13—C14—C9121.84 (14)
C5—C6—C1120.91 (14)C13—C14—H14119.1
C5—C6—H6119.5C9—C14—H14119.1

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.822.022.8131 (15)164
N2—H2B···O4ii0.90 (1)2.22 (1)3.0513 (17)155 (2)
C7—H7···O4ii0.932.413.235 (2)148
C13—H13···O1i0.932.353.0713 (19)134

Symmetry codes: (i) x+1/2, −y+5/2, z−1/2; (ii) x+1/2, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2812).

References

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