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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1503–o1504.
Published online 2009 June 6. doi:  10.1107/S1600536809020820
PMCID: PMC2969228

4-Hydr­oxy-N′-(3,5-dichloro-2-hydroxy­benzyl­idene)benzohydrazide

Abstract

In the title compound, C14H10Cl2N2O3, the dihedral angle between the two benzene rings is 5.1 (2)°. The mol­ecule adopts an E configuration with respect to the C=N bond and an intra­molecular O—H(...)N inter­action is present. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O and O—H(...)O hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999 [triangle]); Ren et al. (2002 [triangle]); Eltayeb et al. (2008 [triangle]); Sinha et al. (2008 [triangle]). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008 [triangle]); Prabhakaran et al. (2006 [triangle]); Dhar et al. (2005 [triangle]). For related structures, see: Cui et al. (2007 [triangle]); Jing et al. (2007 [triangle]); Ma et al. (2008 [triangle]); Salhin et al. (2007 [triangle]); Lin et al. (2007 [triangle]); Alhadi et al. (2008 [triangle]); Xue et al. (2008 [triangle]); Wang et al. (2008 [triangle]); Lu (2008 [triangle]); Diao et al. (2008 [triangle]); Qiu (2009 [triangle]); Mohd Lair et al. (2009a [triangle],b [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1503-scheme1.jpg

Experimental

Crystal data

  • C14H10Cl2N2O3
  • M r = 325.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1503-efi1.jpg
  • a = 8.030 (1) Å
  • b = 13.546 (2) Å
  • c = 13.433 (2) Å
  • β = 107.247 (2)°
  • V = 1395.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.48 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 = 0.911, T max = 0.919
  • 8463 measured reflections
  • 3039 independent reflections
  • 2324 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.107
  • S = 1.03
  • 3039 reflections
  • 195 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020820/bx2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020820/bx2214Isup2.hkl

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

Acknowledgments

The author acknowledges Zaozhuang University for funding this study.

supplementary crystallographic information

Comment

The Schiff base compounds show excellent biological properties (Jeewoth et al., 1999; Ren et al., 2002; Eltayeb et al., 2008; Sinha et al., 2008). Moreover, the Schiff base compounds have been widely used as versatile ligands in coordination chemistry (Shivakumar et al., 2008; Prabhakaran et al., 2006; Dhar et al., 2005). We report here the crystal structure of the title compound. In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 5.1 (2)°. All the bond lengths are within normal values (Allen et al., 1987) and comparable to those in other similar compounds (Cui et al., 2007; Jing et al., 2007; Ma et al., 2008; Salhin et al., 2007; Lin et al., 2007; Alhadi et al., 2008; Xue et al., 2008; Wang et al., 2008; Lu, 2008; Diao et al., 2008; Qiu, 2009; Mohd Lair et al., 2009a,b). —H···N OIn the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), Fig. 2.

Experimental

All the starting materials were obtained with AR grade from Lancaster. 3,5-Dichloro-2-hydroxybenzaldehyde (1.0 mmol, 192.2 mg) and 4-hydroxybenzohydrazide (1.0 mmol, 152.2 mg) were refluxed in 30 ml methanol solution for 30 min giving a clear yellow solution. Yellow block-shaped single crystals of the compound were obtained by slow evaporation of the solution for a week at room temperature.

Refinement

H2 was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å, and with Uiso restrained to 0.08 Å2. Other H atoms were constrained to ideal geometries, with d(C–H) = 0.93 Å, d(O–H) = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the compound with 30% probability ellipsoids. The intramolecular O–H···N hydrogen bond is shown as a dashed line.
Fig. 2.
Molecular packing of the compound with hydrogen bonds drawn as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

Crystal data

C14H10Cl2N2O3F(000) = 664
Mr = 325.14Dx = 1.547 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2634 reflections
a = 8.030 (1) Åθ = 2.2–26.0°
b = 13.546 (2) ŵ = 0.48 mm1
c = 13.433 (2) ÅT = 298 K
β = 107.247 (2)°Block, yellow
V = 1395.5 (3) Å30.20 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3039 independent reflections
Radiation source: fine-focus sealed tube2324 reflections with I > 2σ(I)
graphiteRint = 0.023
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→9
Tmin = 0.911, Tmax = 0.919k = −17→17
8463 measured reflectionsl = −17→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0503P)2 + 0.3954P] where P = (Fo2 + 2Fc2)/3
3039 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = −0.36 e Å3

Special details

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.

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

xyzUiso*/Ueq
Cl1−0.05205 (8)0.19042 (4)1.13049 (5)0.0682 (2)
Cl20.17799 (11)0.43904 (5)1.45283 (5)0.0843 (2)
N10.25047 (18)0.49746 (11)1.00303 (11)0.0382 (3)
N20.31078 (19)0.56552 (10)0.94624 (11)0.0387 (3)
O10.08301 (19)0.33479 (10)1.01678 (10)0.0512 (3)
H10.13140.37450.98850.077*
O20.26379 (19)0.45814 (10)0.81320 (10)0.0540 (4)
O30.55673 (19)0.80001 (10)0.59831 (10)0.0512 (3)
H30.62000.84330.63220.077*
C10.1834 (2)0.45241 (12)1.15726 (13)0.0369 (4)
C20.1046 (2)0.36288 (13)1.11609 (14)0.0384 (4)
C30.0458 (2)0.30054 (13)1.18096 (15)0.0422 (4)
C40.0667 (2)0.32330 (14)1.28362 (15)0.0467 (5)
H40.02750.28041.32590.056*
C50.1470 (3)0.41115 (15)1.32275 (14)0.0479 (5)
C60.2037 (2)0.47558 (14)1.26095 (14)0.0436 (4)
H60.25580.53481.28850.052*
C70.2478 (2)0.52136 (13)1.09426 (13)0.0388 (4)
H70.28730.58331.12080.047*
C80.3119 (2)0.54031 (13)0.84892 (13)0.0366 (4)
C90.3736 (2)0.61545 (12)0.78824 (13)0.0354 (4)
C100.3425 (3)0.59603 (15)0.68236 (14)0.0468 (4)
H100.27990.54000.65320.056*
C110.4035 (3)0.65890 (16)0.62059 (14)0.0497 (5)
H110.38150.64540.55000.060*
C120.4974 (2)0.74196 (13)0.66340 (13)0.0402 (4)
C130.5276 (2)0.76339 (13)0.76825 (13)0.0404 (4)
H130.58930.81990.79690.049*
C140.4656 (2)0.70024 (13)0.82994 (13)0.0383 (4)
H140.48560.71470.90020.046*
H20.352 (3)0.6232 (11)0.9766 (18)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0753 (4)0.0500 (3)0.0806 (4)−0.0224 (3)0.0252 (3)−0.0019 (3)
Cl20.1359 (6)0.0822 (5)0.0491 (3)−0.0081 (4)0.0492 (4)−0.0052 (3)
N10.0398 (8)0.0373 (7)0.0391 (8)0.0010 (6)0.0143 (6)0.0045 (6)
N20.0462 (8)0.0364 (8)0.0361 (8)−0.0036 (6)0.0165 (7)0.0022 (6)
O10.0629 (9)0.0480 (8)0.0433 (7)−0.0110 (6)0.0165 (6)−0.0057 (6)
O20.0730 (10)0.0428 (7)0.0462 (8)−0.0120 (7)0.0174 (7)−0.0068 (6)
O30.0679 (10)0.0503 (8)0.0392 (7)0.0019 (6)0.0218 (7)0.0104 (6)
C10.0357 (9)0.0358 (9)0.0422 (9)0.0033 (7)0.0160 (7)0.0027 (7)
C20.0340 (9)0.0394 (9)0.0421 (9)0.0042 (7)0.0117 (7)0.0021 (7)
C30.0347 (9)0.0383 (9)0.0543 (11)0.0006 (7)0.0140 (8)0.0040 (8)
C40.0438 (10)0.0478 (11)0.0553 (11)0.0066 (8)0.0249 (9)0.0130 (9)
C50.0563 (12)0.0525 (11)0.0413 (10)0.0068 (9)0.0241 (9)0.0032 (8)
C60.0500 (11)0.0404 (9)0.0452 (10)0.0000 (8)0.0212 (9)−0.0030 (8)
C70.0399 (9)0.0355 (9)0.0427 (10)−0.0012 (7)0.0147 (8)−0.0003 (7)
C80.0359 (9)0.0382 (9)0.0343 (9)0.0031 (7)0.0080 (7)0.0008 (7)
C90.0345 (9)0.0392 (9)0.0326 (8)0.0059 (7)0.0102 (7)0.0010 (7)
C100.0527 (11)0.0510 (11)0.0347 (9)−0.0067 (9)0.0098 (8)−0.0043 (8)
C110.0588 (12)0.0615 (12)0.0276 (9)−0.0009 (10)0.0107 (8)−0.0009 (8)
C120.0453 (10)0.0419 (10)0.0351 (9)0.0116 (8)0.0144 (7)0.0106 (7)
C130.0468 (10)0.0376 (9)0.0373 (9)0.0016 (8)0.0132 (8)0.0003 (7)
C140.0453 (10)0.0412 (9)0.0299 (8)0.0037 (7)0.0135 (7)−0.0014 (7)

Geometric parameters (Å, °)

Cl1—C31.7281 (19)C4—C51.381 (3)
Cl2—C51.7321 (19)C4—H40.9300
N1—C71.274 (2)C5—C61.372 (3)
N1—N21.3732 (19)C6—H60.9300
N2—C81.354 (2)C7—H70.9300
N2—H20.899 (10)C8—C91.478 (2)
O1—C21.348 (2)C9—C141.390 (2)
O1—H10.8200C9—C101.394 (2)
O2—C81.228 (2)C10—C111.376 (3)
O3—C121.363 (2)C10—H100.9300
O3—H30.8200C11—C121.381 (3)
C1—C61.389 (2)C11—H110.9300
C1—C21.403 (2)C12—C131.387 (2)
C1—C71.455 (2)C13—C141.383 (2)
C2—C31.393 (2)C13—H130.9300
C3—C41.374 (3)C14—H140.9300
C7—N1—N2118.23 (15)N1—C7—C1120.45 (16)
C8—N2—N1118.12 (14)N1—C7—H7119.8
C8—N2—H2123.3 (16)C1—C7—H7119.8
N1—N2—H2118.5 (16)O2—C8—N2120.98 (16)
C2—O1—H1109.5O2—C8—C9121.77 (15)
C12—O3—H3109.5N2—C8—C9117.26 (15)
C6—C1—C2119.72 (16)C14—C9—C10118.68 (16)
C6—C1—C7118.80 (16)C14—C9—C8124.85 (15)
C2—C1—C7121.47 (15)C10—C9—C8116.40 (16)
O1—C2—C3118.68 (16)C11—C10—C9120.67 (18)
O1—C2—C1123.01 (16)C11—C10—H10119.7
C3—C2—C1118.30 (16)C9—C10—H10119.7
C4—C3—C2121.93 (17)C10—C11—C12120.06 (16)
C4—C3—Cl1119.57 (14)C10—C11—H11120.0
C2—C3—Cl1118.49 (15)C12—C11—H11120.0
C3—C4—C5118.66 (17)O3—C12—C11117.03 (15)
C3—C4—H4120.7O3—C12—C13122.78 (17)
C5—C4—H4120.7C11—C12—C13120.19 (16)
C6—C5—C4121.27 (17)C14—C13—C12119.56 (17)
C6—C5—Cl2119.84 (16)C14—C13—H13120.2
C4—C5—Cl2118.89 (15)C12—C13—H13120.2
C5—C6—C1120.10 (17)C13—C14—C9120.82 (15)
C5—C6—H6120.0C13—C14—H14119.6
C1—C6—H6120.0C9—C14—H14119.6
C7—N1—N2—C8−179.36 (15)C6—C1—C7—N1171.54 (16)
C6—C1—C2—O1−178.94 (16)C2—C1—C7—N1−7.3 (3)
C7—C1—C2—O1−0.1 (3)N1—N2—C8—O2−1.5 (2)
C6—C1—C2—C31.3 (2)N1—N2—C8—C9178.67 (14)
C7—C1—C2—C3−179.91 (16)O2—C8—C9—C14−164.75 (17)
O1—C2—C3—C4178.59 (17)N2—C8—C9—C1415.1 (2)
C1—C2—C3—C4−1.6 (3)O2—C8—C9—C1012.3 (2)
O1—C2—C3—Cl10.0 (2)N2—C8—C9—C10−167.92 (16)
C1—C2—C3—Cl1179.75 (13)C14—C9—C10—C110.8 (3)
C2—C3—C4—C50.6 (3)C8—C9—C10—C11−176.42 (17)
Cl1—C3—C4—C5179.25 (14)C9—C10—C11—C120.3 (3)
C3—C4—C5—C60.7 (3)C10—C11—C12—O3178.78 (17)
C3—C4—C5—Cl2−178.61 (15)C10—C11—C12—C13−1.3 (3)
C4—C5—C6—C1−1.0 (3)O3—C12—C13—C14−179.03 (16)
Cl2—C5—C6—C1178.29 (14)C11—C12—C13—C141.0 (3)
C2—C1—C6—C50.0 (3)C12—C13—C14—C90.1 (3)
C7—C1—C6—C5−178.85 (16)C10—C9—C14—C13−1.0 (3)
N2—N1—C7—C1179.32 (14)C8—C9—C14—C13175.92 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.902.6164 (19)145
O3—H3···O2i0.821.852.658 (2)168
N2—H2···O3ii0.90 (1)2.20 (2)3.000 (2)147 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2214).

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