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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1631.
Published online 2010 June 16. doi:  10.1107/S160053681002180X
PMCID: PMC3006787

N′-(5-Chloro-2-hy­droxy­benzyl­idene)-2-meth­oxy­benzohydrazide

Abstract

The title Schiff base compound, C15H13ClN2O3, was prepared by the reaction of equimolar quanti­ties of 5-chloro-2-hy­droxy­benzaldehyde with 2-meth­oxy­benzohydrazide in a methanol solution. The dihedral angle between the two benzene rings is 20.6 (3)°. An intra­molecular O—H(...)N hydrogen bond may influence the mol­ecular conformation. In the crystal structure, mol­ecules form chains along the b direction via inter­molecular N—H(...)O hydrogen bonds which are bifurcated involving an intra­molecular N—H(...)O hydrogen bond.

Related literature

For the pharmaceutical and medicinal activities of Schiff bases, see: Sriram et al. (2006 [triangle]); Karthikeyan et al. (2006 [triangle]); Dao et al. (2000 [triangle]). For the coordination chemistry of Schiff bases, see: Ali et al. (2008 [triangle]); Kargar et al. (2009 [triangle]); Yeap et al. (2009 [triangle]). For the crystal structures of Schiff base compounds, see: Fun et al. (2009 [triangle]); Nadeem et al. (2009 [triangle]); Eltayeb et al. (2008 [triangle]). For the structures of related Schiff base compounds previously reported by the author, see: Hao (2009a [triangle],b [triangle],c [triangle],d [triangle], 2010 [triangle]). For standard bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1631-scheme1.jpg

Experimental

Crystal data

  • C15H13ClN2O3
  • M r = 304.72
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1631-efi1.jpg
  • a = 15.392 (3) Å
  • b = 9.110 (2) Å
  • c = 20.128 (3) Å
  • V = 2822.4 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 298 K
  • 0.30 × 0.30 × 0.27 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.920, T max = 0.928
  • 9958 measured reflections
  • 3051 independent reflections
  • 1463 reflections with I > 2σ(I)
  • R int = 0.067

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.150
  • S = 0.99
  • 3051 reflections
  • 195 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.27 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/S160053681002180X/lh5065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002180X/lh5065Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff base compounds are a class of important materials used as pharmaceutical and medicinal fields (Sriram et al., 2006; Karthikeyan et al., 2006; Dao et al., 2000). Schiff bases have also been used as versatile ligands in coordination chemistry (Ali et al., 2008; Kargar et al., 2009; Yeap et al., 2009). Recently, the crystal structures of a large number of Schiff base compounds bearing the hydrazone groups have been reported (Fun et al., 2009; Nadeem et al., 2009; Eltayeb et al., 2008). As a continuous work (Hao, 2009a,b,c,d; Hao, 2010), in this paper, the title Schiff base compound, Fig. 1, is reported.

In the title compound, the dihedral angle between the two benzene rings is 20.6 (3)°. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the b direction (Fig. 2).

Experimental

5-Chloro-2-hydroxybenzaldehyde (0.1 mmol, 15.6 mg) and 2-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were refluxed in a 30 ml methanol solution for 30 min to give a clear colorless solution. Colorless block-shaped single crystals of the compound were formed by slow evaporation of the solvent over several days at room temperature.

Refinement

H2A was located from a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1)Å, and with Uiso fixed at 0.08Å2. Other H atoms were constrained to ideal geometries, with d(C—H) = 0.93-0.96Å, d(O—H) = 0.82Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and C15).

Figures

Fig. 1.
The molecular structure of the title compound with 30% probability ellipsoids. Intramolecular hydrogen bonds are drawn as dashed lines.
Fig. 2.
Molecular packing of the title compound with hydrogen bonds drawn as dashed lines.

Crystal data

C15H13ClN2O3F(000) = 1264
Mr = 304.72Dx = 1.434 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 868 reflections
a = 15.392 (3) Åθ = 2.4–24.5°
b = 9.110 (2) ŵ = 0.28 mm1
c = 20.128 (3) ÅT = 298 K
V = 2822.4 (9) Å3Block, colorless
Z = 80.30 × 0.30 × 0.27 mm

Data collection

Bruker SMART CCD area-detector diffractometer3051 independent reflections
Radiation source: fine-focus sealed tube1463 reflections with I > 2σ(I)
graphiteRint = 0.067
ω scansθmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −19→9
Tmin = 0.920, Tmax = 0.928k = −9→11
9958 measured reflectionsl = −21→25

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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H atoms treated by a mixture of independent and constrained refinement
S = 0.99w = 1/[σ2(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/3
3051 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.17 e Å3
1 restraintΔρmin = −0.27 e Å3

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
Cl11.23358 (6)1.00596 (10)0.43870 (5)0.0931 (4)
N10.83185 (15)1.0819 (2)0.38838 (11)0.0491 (6)
N20.76629 (15)1.0034 (2)0.35851 (13)0.0532 (7)
O10.89608 (14)1.2927 (2)0.46463 (12)0.0713 (7)
H10.85751.24520.44660.107*
O20.67478 (12)1.1960 (2)0.36350 (11)0.0626 (6)
O30.71657 (13)0.8451 (2)0.24964 (11)0.0675 (6)
C10.9728 (2)1.2226 (3)0.45691 (15)0.0547 (8)
C21.0460 (2)1.2825 (3)0.48644 (16)0.0670 (9)
H21.04101.36900.51070.080*
C31.1255 (2)1.2168 (4)0.48063 (16)0.0710 (10)
H31.17411.25790.50070.085*
C41.13245 (19)1.0896 (4)0.44478 (16)0.0600 (8)
C51.06147 (18)1.0276 (3)0.41535 (16)0.0557 (8)
H51.06760.94070.39160.067*
C60.97993 (17)1.0929 (3)0.42047 (14)0.0477 (7)
C70.90686 (18)1.0219 (3)0.38947 (14)0.0487 (7)
H70.91440.93050.36980.058*
C80.68942 (18)1.0680 (3)0.34816 (13)0.0467 (7)
C90.61993 (17)0.9746 (3)0.31858 (15)0.0494 (7)
C100.53588 (19)1.0005 (3)0.34012 (16)0.0573 (8)
H100.52591.07370.37140.069*
C110.4666 (2)0.9204 (4)0.31633 (18)0.0675 (9)
H110.41080.93750.33220.081*
C120.4811 (2)0.8159 (4)0.26919 (19)0.0721 (10)
H120.43460.76240.25240.086*
C130.5630 (2)0.7886 (3)0.24629 (17)0.0654 (9)
H130.57160.71700.21400.078*
C140.63371 (19)0.8664 (3)0.27054 (15)0.0519 (8)
C150.7318 (2)0.7299 (4)0.20290 (18)0.0821 (11)
H15A0.71090.63880.22080.123*
H15B0.79300.72220.19430.123*
H15C0.70180.75130.16220.123*
H2A0.7748 (19)0.9090 (14)0.3487 (15)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0545 (5)0.1169 (8)0.1077 (9)−0.0004 (5)−0.0070 (5)0.0248 (6)
N10.0517 (14)0.0446 (13)0.0510 (16)−0.0044 (11)−0.0067 (12)−0.0020 (12)
N20.0528 (14)0.0403 (13)0.0666 (18)0.0001 (12)−0.0152 (12)−0.0101 (13)
O10.0792 (16)0.0573 (13)0.0775 (17)0.0036 (11)0.0003 (13)−0.0150 (12)
O20.0662 (13)0.0397 (11)0.0821 (16)0.0041 (9)−0.0057 (11)−0.0110 (11)
O30.0613 (13)0.0702 (14)0.0709 (15)−0.0022 (10)−0.0046 (12)−0.0297 (12)
C10.070 (2)0.0471 (18)0.0470 (19)−0.0062 (15)0.0006 (16)0.0012 (15)
C20.092 (3)0.055 (2)0.053 (2)−0.0216 (18)−0.0115 (18)−0.0081 (17)
C30.068 (2)0.084 (3)0.062 (2)−0.029 (2)−0.0157 (18)0.012 (2)
C40.0542 (18)0.071 (2)0.055 (2)−0.0117 (16)−0.0066 (16)0.0146 (18)
C50.0583 (19)0.0567 (18)0.0521 (19)−0.0077 (14)−0.0017 (15)0.0031 (16)
C60.0528 (17)0.0460 (16)0.0443 (18)−0.0091 (13)−0.0031 (14)0.0041 (14)
C70.0556 (18)0.0408 (16)0.0497 (19)−0.0043 (13)0.0001 (14)−0.0026 (14)
C80.0556 (18)0.0415 (16)0.0428 (18)−0.0015 (13)−0.0012 (14)−0.0010 (14)
C90.0533 (17)0.0428 (16)0.0523 (19)0.0023 (13)−0.0116 (14)0.0046 (15)
C100.060 (2)0.0517 (18)0.060 (2)0.0040 (15)−0.0089 (16)0.0027 (15)
C110.0522 (19)0.071 (2)0.080 (3)−0.0043 (16)−0.0053 (18)0.012 (2)
C120.063 (2)0.070 (2)0.082 (3)−0.0143 (17)−0.0148 (19)0.006 (2)
C130.070 (2)0.0587 (19)0.068 (2)−0.0113 (16)−0.0126 (18)−0.0106 (17)
C140.0526 (18)0.0482 (17)0.055 (2)0.0008 (14)−0.0085 (15)−0.0001 (16)
C150.079 (2)0.079 (2)0.088 (3)0.0057 (18)−0.005 (2)−0.033 (2)

Geometric parameters (Å, °)

Cl1—C41.737 (3)C5—H50.9300
N1—C71.278 (3)C6—C71.439 (4)
N1—N21.375 (3)C7—H70.9300
N2—C81.338 (3)C8—C91.491 (4)
N2—H2A0.892 (10)C9—C101.385 (4)
O1—C11.351 (3)C9—C141.397 (4)
O1—H10.8200C10—C111.377 (4)
O2—C81.227 (3)C10—H100.9300
O3—C141.357 (3)C11—C121.363 (5)
O3—C151.429 (3)C11—H110.9300
C1—C21.386 (4)C12—C131.365 (4)
C1—C61.395 (4)C12—H120.9300
C2—C31.367 (5)C13—C141.387 (4)
C2—H20.9300C13—H130.9300
C3—C41.369 (4)C15—H15A0.9600
C3—H30.9300C15—H15B0.9600
C4—C51.365 (4)C15—H15C0.9600
C5—C61.393 (4)
C7—N1—N2116.6 (2)O2—C8—N2122.8 (2)
C8—N2—N1119.2 (2)O2—C8—C9120.8 (2)
C8—N2—H2A121 (2)N2—C8—C9116.5 (2)
N1—N2—H2A119 (2)C10—C9—C14118.6 (3)
C1—O1—H1109.5C10—C9—C8116.6 (3)
C14—O3—C15117.6 (2)C14—C9—C8124.8 (3)
O1—C1—C2118.4 (3)C11—C10—C9121.6 (3)
O1—C1—C6122.0 (3)C11—C10—H10119.2
C2—C1—C6119.6 (3)C9—C10—H10119.2
C3—C2—C1121.3 (3)C12—C11—C10119.1 (3)
C3—C2—H2119.4C12—C11—H11120.5
C1—C2—H2119.4C10—C11—H11120.5
C2—C3—C4119.0 (3)C11—C12—C13120.9 (3)
C2—C3—H3120.5C11—C12—H12119.6
C4—C3—H3120.5C13—C12—H12119.6
C5—C4—C3121.1 (3)C12—C13—C14120.8 (3)
C5—C4—Cl1120.4 (3)C12—C13—H13119.6
C3—C4—Cl1118.6 (3)C14—C13—H13119.6
C4—C5—C6120.9 (3)O3—C14—C13123.7 (3)
C4—C5—H5119.6O3—C14—C9117.3 (2)
C6—C5—H5119.6C13—C14—C9119.0 (3)
C5—C6—C1118.1 (3)O3—C15—H15A109.5
C5—C6—C7118.7 (3)O3—C15—H15B109.5
C1—C6—C7123.1 (3)H15A—C15—H15B109.5
N1—C7—C6121.4 (3)O3—C15—H15C109.5
N1—C7—H7119.3H15A—C15—H15C109.5
C6—C7—H7119.3H15B—C15—H15C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.932.649 (3)145
N2—H2A···O2i0.89 (1)2.11 (2)2.946 (3)155 (3)
N2—H2A···O30.89 (1)2.26 (3)2.733 (3)113 (2)

Symmetry codes: (i) −x+3/2, y−1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5065).

References

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