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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o875–o876.
Published online 2010 March 20. doi:  10.1107/S1600536810009645
PMCID: PMC2983793

N′-(2,4-Dichloro­benzyl­idene)-3-methoxy­benzohydrazide

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C15H12Cl2N2O2. The dihedral angle between the two benzene rings is 27.6 (4)° in one mol­ecule and 16.4 (4)° in the other. Both mol­ecules adopt an E configuration about the C=N bonds. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds, forming chains in the a-axis direction.

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 the structures of related Schiff bases previously reported by the author, see: Ren (2009a [triangle],b [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-66-0o875-scheme1.jpg

Experimental

Crystal data

  • C15H12Cl2N2O2
  • M r = 323.17
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o875-efi1.jpg
  • a = 8.298 (1) Å
  • b = 12.988 (2) Å
  • c = 14.138 (2) Å
  • α = 88.746 (3)°
  • β = 87.711 (2)°
  • γ = 84.020 (3)°
  • V = 1514.0 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.43 mm−1
  • T = 298 K
  • 0.10 × 0.08 × 0.08 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.958, T max = 0.966
  • 6065 measured reflections
  • 4120 independent reflections
  • 2565 reflections with I > 2σ(I)
  • R int = 0.024
  • θmax = 22.9°

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.121
  • S = 1.02
  • 4120 reflections
  • 381 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.21 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/S1600536810009645/sj2748sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810009645/sj2748Isup2.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). Recently, the author has reported a few Schiff bases (Ren, 2009a,b). In this paper, the title new Schiff base compound is reported.

In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 27.6 (4)° in one molecule and 16.4 (4)° in another molecule. 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).

In the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), forming chains toward the a direction (Fig. 2).

Experimental

All the starting materials were obtained with AR grade from Lancaster. 2,4-Dichlorobenzaldehyde (1.0 mmol, 174.0 mg) and 3-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were refluxed in a 30 ml me thanol solution for 30 min to give a clear colorless solution. Colorless needle-shaped single crystals of the compound were obtained by slow evaporation of the solution for a week at room temperature.

Refinement

H atoms were constrained to ideal geometries, with d(C–H) = 0.93 Å, d(N–H) = 0.86 Å, and with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(Cmethyl). The resolution is 22.92°, and the sin(theta)/Lambda < 0.6, which is caused by the weak diffraction of the crystal.

Figures

Fig. 1.
The molecular structure of the compound with 30% probability ellipsoids.
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

C15H12Cl2N2O2Z = 4
Mr = 323.17F(000) = 664
Triclinic, P1Dx = 1.418 Mg m3
a = 8.298 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.988 (2) ÅCell parameters from 1156 reflections
c = 14.138 (2) Åθ = 2.8–23.5°
α = 88.746 (3)°µ = 0.43 mm1
β = 87.711 (2)°T = 298 K
γ = 84.020 (3)°Block, colorless
V = 1514.0 (4) Å30.10 × 0.08 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer4120 independent reflections
Radiation source: fine-focus sealed tube2565 reflections with I > 2σ(I)
graphiteRint = 0.024
ω scansθmax = 22.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.958, Tmax = 0.966k = −10→14
6065 measured reflectionsl = −15→15

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0469P)2 + 0.2383P] where P = (Fo2 + 2Fc2)/3
4120 reflections(Δ/σ)max = 0.001
381 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.21 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 > 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
Cl10.30439 (13)0.32267 (9)1.09237 (7)0.0867 (4)
Cl20.83230 (16)0.50607 (10)1.16976 (8)0.1062 (5)
Cl30.1167 (2)0.70669 (11)0.60769 (9)0.1330 (6)
Cl4−0.35105 (15)0.45751 (9)0.67302 (8)0.1007 (4)
N10.4406 (3)0.2114 (2)0.75587 (19)0.0555 (8)
H10.34120.20330.77090.067*
N20.5340 (3)0.2588 (2)0.8166 (2)0.0531 (7)
N3−0.0370 (3)0.7340 (2)0.3205 (2)0.0556 (8)
N40.0573 (3)0.7900 (2)0.2608 (2)0.0574 (8)
H4A0.15000.80560.27770.069*
O10.6495 (3)0.18861 (18)0.64745 (16)0.0631 (7)
O20.3350 (4)0.1097 (3)0.3553 (2)0.1031 (10)
O30.2072 (4)0.9215 (3)−0.1371 (2)0.1031 (10)
O4−0.1296 (3)0.79782 (19)0.14806 (16)0.0669 (7)
C10.3271 (5)0.0976 (3)0.4518 (3)0.0720 (12)
C20.2182 (5)0.0314 (3)0.4875 (4)0.0827 (14)
H20.1565−0.00140.44620.099*
C30.2003 (5)0.0137 (3)0.5828 (3)0.0762 (12)
H30.1272−0.03130.60570.091*
C40.2901 (4)0.0622 (3)0.6454 (3)0.0595 (10)
H40.27640.05130.71030.071*
C50.4007 (4)0.1271 (2)0.6100 (2)0.0472 (8)
C60.4199 (4)0.1441 (3)0.5135 (2)0.0593 (10)
H60.49590.18700.49030.071*
C70.4439 (7)0.1770 (4)0.3170 (3)0.121 (2)
H7A0.41260.24580.33910.181*
H7B0.44200.17690.24920.181*
H7C0.55140.15410.33660.181*
C80.5085 (4)0.1778 (3)0.6720 (2)0.0502 (9)
C90.4671 (4)0.2843 (3)0.8961 (2)0.0542 (9)
H90.36170.26950.91090.065*
C100.5559 (4)0.3368 (2)0.9639 (2)0.0496 (9)
C110.7065 (4)0.3690 (3)0.9398 (2)0.0573 (10)
H110.75030.35660.87900.069*
C120.7937 (4)0.4184 (3)1.0020 (3)0.0647 (10)
H120.89550.43760.98400.078*
C130.7290 (5)0.4392 (3)1.0910 (3)0.0660 (11)
C140.5802 (5)0.4090 (3)1.1195 (3)0.0677 (11)
H140.53760.42221.18030.081*
C150.4949 (4)0.3583 (3)1.0553 (3)0.0568 (9)
C160.1987 (5)0.9281 (3)−0.0409 (3)0.0718 (11)
C170.1040 (4)0.8705 (3)0.0187 (3)0.0618 (10)
H170.03830.8248−0.00620.074*
C180.1085 (4)0.8818 (3)0.1148 (3)0.0525 (9)
C190.2046 (4)0.9498 (3)0.1527 (3)0.0704 (11)
H190.20850.95610.21790.084*
C200.2954 (5)1.0084 (3)0.0920 (4)0.0891 (14)
H200.35891.05560.11650.107*
C210.2917 (5)0.9971 (4)−0.0028 (4)0.0869 (14)
H210.35321.0368−0.04280.104*
C220.1221 (7)0.8470 (4)−0.1775 (3)0.1154 (19)
H22A0.15670.7799−0.15110.173*
H22B0.14320.8467−0.24470.173*
H22C0.00800.8632−0.16420.173*
C230.0139 (4)0.7167 (3)0.4036 (3)0.0564 (9)
H230.10820.74290.42120.068*
C24−0.0752 (4)0.6559 (3)0.4711 (2)0.0527 (9)
C25−0.0405 (5)0.6459 (3)0.5646 (3)0.0659 (10)
C26−0.1259 (5)0.5868 (3)0.6285 (3)0.0726 (12)
H26−0.10050.58200.69200.087*
C27−0.2481 (5)0.5360 (3)0.5956 (3)0.0683 (11)
C28−0.2864 (5)0.5438 (3)0.5027 (3)0.0778 (12)
H28−0.36980.50900.48100.093*
C29−0.2012 (4)0.6033 (3)0.4413 (3)0.0674 (11)
H29−0.22850.60870.37810.081*
C300.0012 (4)0.8200 (3)0.1750 (3)0.0531 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0859 (8)0.1052 (9)0.0706 (7)−0.0250 (7)0.0176 (6)−0.0033 (6)
Cl20.1145 (10)0.1176 (10)0.0918 (9)−0.0174 (8)−0.0375 (7)−0.0345 (7)
Cl30.1856 (15)0.1449 (12)0.0878 (9)−0.0930 (11)−0.0557 (9)0.0140 (8)
Cl40.1080 (10)0.1002 (9)0.0905 (9)−0.0132 (7)0.0349 (7)0.0183 (7)
N10.0392 (17)0.075 (2)0.0551 (19)−0.0155 (16)−0.0011 (15)−0.0138 (16)
N20.0478 (18)0.0611 (19)0.0521 (19)−0.0122 (15)−0.0036 (15)−0.0047 (15)
N30.0415 (18)0.067 (2)0.058 (2)−0.0088 (15)0.0041 (16)0.0035 (16)
N40.0361 (17)0.077 (2)0.061 (2)−0.0155 (16)−0.0023 (15)0.0086 (16)
O10.0404 (15)0.0914 (19)0.0610 (16)−0.0221 (14)0.0026 (12)−0.0127 (13)
O20.113 (3)0.130 (3)0.065 (2)0.007 (2)−0.0319 (18)−0.015 (2)
O30.123 (3)0.104 (3)0.075 (2)0.006 (2)0.031 (2)0.0132 (19)
O40.0465 (16)0.095 (2)0.0618 (16)−0.0221 (14)−0.0070 (13)0.0059 (14)
C10.069 (3)0.088 (3)0.055 (3)0.018 (3)−0.019 (2)−0.019 (2)
C20.053 (3)0.095 (3)0.102 (4)−0.002 (3)−0.029 (3)−0.035 (3)
C30.053 (3)0.076 (3)0.102 (4)−0.014 (2)−0.005 (2)−0.017 (3)
C40.042 (2)0.068 (2)0.069 (3)−0.007 (2)−0.0035 (19)−0.011 (2)
C50.038 (2)0.054 (2)0.049 (2)−0.0020 (18)−0.0058 (16)−0.0042 (17)
C60.052 (2)0.068 (3)0.057 (2)−0.001 (2)−0.0038 (19)−0.005 (2)
C70.180 (6)0.118 (4)0.058 (3)0.020 (4)−0.016 (3)0.007 (3)
C80.045 (2)0.056 (2)0.050 (2)−0.0073 (19)−0.0034 (18)−0.0003 (18)
C90.045 (2)0.062 (2)0.056 (2)−0.0084 (19)−0.0048 (18)−0.0019 (19)
C100.051 (2)0.049 (2)0.048 (2)−0.0026 (18)−0.0083 (18)−0.0001 (17)
C110.048 (2)0.065 (2)0.059 (2)−0.004 (2)−0.0059 (19)−0.0113 (19)
C120.057 (2)0.070 (3)0.069 (3)−0.011 (2)−0.009 (2)−0.006 (2)
C130.071 (3)0.058 (2)0.070 (3)−0.001 (2)−0.023 (2)−0.010 (2)
C140.086 (3)0.066 (3)0.050 (2)0.004 (2)−0.011 (2)−0.006 (2)
C150.060 (2)0.053 (2)0.056 (2)−0.0006 (19)−0.0043 (19)0.0035 (19)
C160.065 (3)0.079 (3)0.066 (3)0.012 (2)0.011 (2)0.012 (2)
C170.052 (2)0.066 (3)0.066 (3)−0.003 (2)0.008 (2)0.004 (2)
C180.038 (2)0.055 (2)0.062 (3)0.0000 (18)0.0044 (18)0.0057 (19)
C190.057 (3)0.075 (3)0.082 (3)−0.018 (2)−0.010 (2)0.012 (2)
C200.069 (3)0.085 (3)0.117 (4)−0.027 (3)−0.017 (3)0.019 (3)
C210.052 (3)0.094 (4)0.113 (4)−0.014 (3)0.002 (3)0.031 (3)
C220.180 (6)0.099 (4)0.059 (3)0.010 (4)0.023 (3)−0.003 (3)
C230.050 (2)0.063 (2)0.058 (2)−0.0098 (19)−0.004 (2)0.0012 (19)
C240.049 (2)0.054 (2)0.055 (2)−0.0016 (19)0.0003 (18)−0.0036 (18)
C250.082 (3)0.060 (2)0.057 (3)−0.012 (2)−0.010 (2)−0.002 (2)
C260.103 (4)0.066 (3)0.047 (2)−0.002 (3)−0.001 (2)0.001 (2)
C270.067 (3)0.063 (3)0.072 (3)−0.002 (2)0.024 (2)−0.001 (2)
C280.055 (3)0.108 (3)0.071 (3)−0.020 (2)0.007 (2)0.004 (3)
C290.054 (2)0.098 (3)0.051 (2)−0.016 (2)0.002 (2)0.003 (2)
C300.040 (2)0.061 (2)0.057 (2)−0.0032 (19)0.0033 (19)−0.0022 (19)

Geometric parameters (Å, °)

Cl1—C151.750 (4)C10—C111.387 (4)
Cl2—C131.733 (4)C10—C151.392 (4)
Cl3—C251.730 (4)C11—C121.371 (4)
Cl4—C271.739 (4)C11—H110.9300
N1—C81.353 (4)C12—C131.369 (5)
N1—N21.376 (3)C12—H120.9300
N1—H10.8600C13—C141.377 (5)
N2—C91.268 (4)C14—C151.390 (5)
N3—C231.272 (4)C14—H140.9300
N3—N41.376 (3)C16—C211.374 (5)
N4—C301.351 (4)C16—C171.389 (5)
N4—H4A0.8600C17—C181.372 (5)
O1—C81.229 (3)C17—H170.9300
O2—C11.369 (4)C18—C191.380 (5)
O2—C71.406 (5)C18—C301.490 (4)
O3—C161.363 (4)C19—C201.387 (5)
O3—C221.400 (5)C19—H190.9300
O4—C301.229 (4)C20—C211.354 (6)
C1—C61.376 (5)C20—H200.9300
C1—C21.385 (6)C21—H210.9300
C2—C31.366 (5)C22—H22A0.9600
C2—H20.9300C22—H22B0.9600
C3—C41.382 (5)C22—H22C0.9600
C3—H30.9300C23—C241.454 (4)
C4—C51.382 (4)C23—H230.9300
C4—H40.9300C24—C251.366 (5)
C5—C61.382 (4)C24—C291.390 (5)
C5—C81.488 (4)C25—C261.392 (5)
C6—H60.9300C26—C271.367 (5)
C7—H7A0.9600C26—H260.9300
C7—H7B0.9600C27—C281.363 (5)
C7—H7C0.9600C28—C291.374 (5)
C9—C101.455 (4)C28—H280.9300
C9—H90.9300C29—H290.9300
C8—N1—N2118.6 (3)C13—C14—H14120.7
C8—N1—H1120.7C15—C14—H14120.7
N2—N1—H1120.7C14—C15—C10122.0 (3)
C9—N2—N1116.1 (3)C14—C15—Cl1117.8 (3)
C23—N3—N4116.0 (3)C10—C15—Cl1120.2 (3)
C30—N4—N3118.6 (3)O3—C16—C21116.1 (4)
C30—N4—H4A120.7O3—C16—C17124.4 (4)
N3—N4—H4A120.7C21—C16—C17119.4 (4)
C1—O2—C7117.1 (4)C18—C17—C16119.3 (4)
C16—O3—C22117.3 (4)C18—C17—H17120.4
O2—C1—C6125.1 (4)C16—C17—H17120.4
O2—C1—C2115.8 (4)C17—C18—C19121.0 (3)
C6—C1—C2119.1 (4)C17—C18—C30116.8 (3)
C3—C2—C1120.7 (4)C19—C18—C30122.2 (3)
C3—C2—H2119.6C18—C19—C20119.0 (4)
C1—C2—H2119.6C18—C19—H19120.5
C2—C3—C4120.5 (4)C20—C19—H19120.5
C2—C3—H3119.7C21—C20—C19120.1 (4)
C4—C3—H3119.7C21—C20—H20119.9
C3—C4—C5118.9 (4)C19—C20—H20119.9
C3—C4—H4120.5C20—C21—C16121.2 (4)
C5—C4—H4120.5C20—C21—H21119.4
C6—C5—C4120.5 (3)C16—C21—H21119.4
C6—C5—C8117.1 (3)O3—C22—H22A109.5
C4—C5—C8122.4 (3)O3—C22—H22B109.5
C1—C6—C5120.2 (4)H22A—C22—H22B109.5
C1—C6—H6119.9O3—C22—H22C109.5
C5—C6—H6119.9H22A—C22—H22C109.5
O2—C7—H7A109.5H22B—C22—H22C109.5
O2—C7—H7B109.5N3—C23—C24120.0 (3)
H7A—C7—H7B109.5N3—C23—H23120.0
O2—C7—H7C109.5C24—C23—H23120.0
H7A—C7—H7C109.5C25—C24—C29116.8 (3)
H7B—C7—H7C109.5C25—C24—C23123.1 (3)
O1—C8—N1122.8 (3)C29—C24—C23120.1 (3)
O1—C8—C5121.5 (3)C24—C25—C26122.5 (4)
N1—C8—C5115.7 (3)C24—C25—Cl3120.0 (3)
N2—C9—C10119.8 (3)C26—C25—Cl3117.4 (3)
N2—C9—H9120.1C27—C26—C25118.5 (4)
C10—C9—H9120.1C27—C26—H26120.8
C11—C10—C15116.5 (3)C25—C26—H26120.8
C11—C10—C9121.1 (3)C28—C27—C26120.8 (4)
C15—C10—C9122.4 (3)C28—C27—Cl4119.9 (4)
C12—C11—C10122.6 (3)C26—C27—Cl4119.3 (3)
C12—C11—H11118.7C27—C28—C29119.6 (4)
C10—C11—H11118.7C27—C28—H28120.2
C13—C12—C11119.2 (4)C29—C28—H28120.2
C13—C12—H12120.4C28—C29—C24121.8 (4)
C11—C12—H12120.4C28—C29—H29119.1
C12—C13—C14121.0 (3)C24—C29—H29119.1
C12—C13—Cl2120.4 (3)O4—C30—N4122.4 (3)
C14—C13—Cl2118.6 (3)O4—C30—C18122.0 (3)
C13—C14—C15118.6 (3)N4—C30—C18115.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···O1i0.862.022.844 (4)161
N1—H1···O4ii0.862.062.880 (3)159

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2748).

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