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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3143.
Published online 2010 November 13. doi:  10.1107/S1600536810045502
PMCID: PMC3011548

N′-(2,4-Dichloro­benzyl­idene)-4-hy­droxy­benzohydrazide

Abstract

The title hydrazone compound, C14H10Cl2N2O2, was synthesized by the reaction of 2,4-dichloro­benzaldehyde and 4-hy­droxy­benzohydrazide. The mol­ecule adopts an E geometry with respect to the azomethine group and the dihedral angle between the aromatic rings is 7.0 (2)°. In the crystal, mol­ecules are linked through inter­molecular N—H(...)Cl and O—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

For the structures and properties of hydrazones, see: Carvalho et al. (2010 [triangle]); Liu (2010 [triangle]); Fun et al. (2008 [triangle]); Wang et al. (2010 [triangle]); Singh et al. (2009 [triangle]); Zhu et al. (2009 [triangle]); Vijayakumar et al. (2009 [triangle]); Tameem et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3143-scheme1.jpg

Experimental

Crystal data

  • C14H10Cl2N2O2
  • M r = 309.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3143-efi1.jpg
  • a = 7.6687 (11) Å
  • b = 11.9591 (17) Å
  • c = 15.043 (2) Å
  • β = 103.200 (2)°
  • V = 1343.2 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.49 mm−1
  • T = 298 K
  • 0.17 × 0.13 × 0.13 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.922, T max = 0.940
  • 6784 measured reflections
  • 2838 independent reflections
  • 2385 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.114
  • S = 1.05
  • 2838 reflections
  • 185 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.58 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/S1600536810045502/hb5726sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045502/hb5726Isup2.hkl

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

Acknowledgments

This work was supported by Yichun University.

supplementary crystallographic information

Comment

The hydrazone compounds bearing –CH=N—NH—C(O)- groups have been received much attention for their structures (Carvalho et al., 2010; Liu, 2010; Fun et al., 2008; Wang et al., 2010) and properties (Singh et al., 2009; Zhu et al., 2009; Vijayakumar et al., 2009; Tameem et al., 2010). In this paper, the title new hydrazone compound is reported.

The molecular structure of the title compound is shown in Fig. 1. The molecule adopts an E geometry with respect to the azomethine group. The dihedral angle between the two aromatic rings C1—C6 and C9—C14 is 7.0 (2)°. In the crystal structure, molecules are linked through intermolecular N–H···Cl and O–H···O hydrogen bonds to form a three-dimensional network (Table 1, Fig. 2).

Experimental

Equimolar quantities (0.1 mmol each) of 2,4-dichlorobenzaldehyde and 4-hydroxybenzohydrazide were mixed and stirred in methanol for 30 min at reflux. After keeping the filtrate in air for a few days, colorless blocks of the title compound were formed.

Refinement

H2 attached to N2 was located from a difference Fourier map, and refined with N–H distance restrained to 0.90 (1) Å, and with Uiso restrained to 0.08 Å2. The remaining H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C—H distances of 0.93 Å, O—H distance of 0.85 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).

Figures

Fig. 1.
Molecular structure of the title compound, with 30% ellipsoids.
Fig. 2.
The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are drawn as thin dashed lines.

Crystal data

C14H10Cl2N2O2F(000) = 632
Mr = 309.14Dx = 1.529 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3439 reflections
a = 7.6687 (11) Åθ = 2.2–28.1°
b = 11.9591 (17) ŵ = 0.49 mm1
c = 15.043 (2) ÅT = 298 K
β = 103.200 (2)°Block, colorless
V = 1343.2 (3) Å30.17 × 0.13 × 0.13 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2838 independent reflections
Radiation source: fine-focus sealed tube2385 reflections with I > 2σ(I)
graphiteRint = 0.019
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.922, Tmax = 0.940k = −7→15
6784 measured reflectionsl = −19→17

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0636P)2 + 0.4165P] where P = (Fo2 + 2Fc2)/3
2838 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.37 e Å3
1 restraintΔρmin = −0.58 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
Cl11.05089 (9)0.19236 (5)0.07396 (3)0.0590 (2)
Cl20.99147 (8)0.02938 (5)−0.26115 (4)0.05604 (19)
N10.7367 (2)0.47578 (12)−0.05039 (10)0.0350 (3)
N20.7130 (2)0.55434 (12)0.01223 (10)0.0363 (3)
O10.5166 (2)0.65200 (12)−0.09421 (8)0.0476 (4)
O20.5103 (2)0.96168 (11)0.24525 (9)0.0472 (4)
H2A0.53290.93600.29710.071*
C10.8721 (2)0.30387 (14)−0.07778 (12)0.0322 (4)
C20.9708 (2)0.20915 (15)−0.04294 (12)0.0360 (4)
C31.0075 (2)0.12484 (15)−0.09862 (12)0.0388 (4)
H31.07450.0628−0.07410.047*
C40.9423 (2)0.13500 (15)−0.19144 (12)0.0372 (4)
C50.8419 (2)0.22625 (15)−0.22950 (12)0.0385 (4)
H50.79840.2313−0.29240.046*
C60.8074 (2)0.30948 (15)−0.17268 (12)0.0351 (4)
H60.73950.3709−0.19790.042*
C70.8350 (2)0.39312 (15)−0.01809 (12)0.0365 (4)
H70.88400.38920.04440.044*
C80.5992 (2)0.64163 (14)−0.01442 (11)0.0325 (4)
C90.5824 (2)0.72236 (13)0.05731 (11)0.0307 (4)
C100.6378 (2)0.70117 (15)0.15075 (12)0.0358 (4)
H100.69070.63290.17040.043*
C110.6154 (2)0.77948 (15)0.21432 (11)0.0375 (4)
H110.65300.76370.27630.045*
C120.5367 (2)0.88225 (14)0.18611 (11)0.0338 (4)
C130.4802 (3)0.90445 (15)0.09322 (12)0.0391 (4)
H130.42760.97290.07360.047*
C140.5020 (3)0.82533 (14)0.03025 (11)0.0370 (4)
H140.46230.8408−0.03170.044*
H20.767 (3)0.542 (2)0.0707 (8)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0820 (4)0.0559 (3)0.0333 (3)0.0123 (3)0.0010 (2)−0.0002 (2)
Cl20.0620 (3)0.0532 (3)0.0521 (3)0.0072 (2)0.0113 (2)−0.0228 (2)
N10.0433 (8)0.0303 (7)0.0336 (7)−0.0054 (6)0.0135 (6)−0.0062 (6)
N20.0461 (8)0.0315 (7)0.0307 (7)0.0008 (6)0.0074 (6)−0.0064 (6)
O10.0696 (10)0.0455 (8)0.0266 (6)0.0091 (7)0.0087 (6)−0.0004 (5)
O20.0715 (9)0.0374 (7)0.0341 (7)0.0030 (6)0.0149 (7)−0.0066 (5)
C10.0344 (9)0.0301 (8)0.0339 (8)−0.0059 (6)0.0117 (7)−0.0039 (7)
C20.0391 (9)0.0356 (9)0.0327 (8)−0.0034 (7)0.0071 (7)−0.0019 (7)
C30.0398 (10)0.0332 (9)0.0426 (10)0.0007 (7)0.0077 (8)−0.0033 (7)
C40.0367 (9)0.0364 (9)0.0406 (9)−0.0051 (7)0.0132 (7)−0.0114 (7)
C50.0429 (10)0.0425 (10)0.0308 (8)−0.0025 (8)0.0098 (7)−0.0034 (7)
C60.0377 (9)0.0326 (9)0.0360 (9)−0.0027 (7)0.0106 (7)0.0006 (7)
C70.0433 (10)0.0348 (9)0.0321 (8)−0.0041 (7)0.0097 (7)−0.0045 (7)
C80.0410 (9)0.0302 (8)0.0279 (8)−0.0062 (7)0.0111 (7)0.0000 (6)
C90.0356 (9)0.0285 (8)0.0291 (8)−0.0048 (6)0.0098 (6)−0.0003 (6)
C100.0418 (10)0.0357 (9)0.0299 (8)0.0070 (7)0.0082 (7)0.0037 (7)
C110.0443 (10)0.0422 (10)0.0251 (8)0.0050 (8)0.0060 (7)0.0015 (7)
C120.0416 (9)0.0304 (8)0.0314 (8)−0.0062 (7)0.0124 (7)−0.0032 (7)
C130.0576 (11)0.0261 (8)0.0342 (9)0.0001 (8)0.0117 (8)0.0045 (7)
C140.0528 (11)0.0319 (9)0.0259 (8)−0.0026 (7)0.0082 (7)0.0037 (6)

Geometric parameters (Å, °)

Cl1—C21.7369 (18)C5—C61.377 (2)
Cl2—C41.7372 (18)C5—H50.9300
N1—C71.270 (2)C6—H60.9300
N1—N21.372 (2)C7—H70.9300
N2—C81.361 (2)C8—C91.475 (2)
N2—H20.894 (10)C9—C101.396 (2)
O1—C81.229 (2)C9—C141.396 (2)
O2—C121.348 (2)C10—C111.377 (2)
O2—H2A0.8200C10—H100.9300
C1—C21.396 (2)C11—C121.392 (2)
C1—C61.402 (2)C11—H110.9300
C1—C71.464 (2)C12—C131.391 (2)
C2—C31.380 (2)C13—C141.376 (2)
C3—C41.377 (3)C13—H130.9300
C3—H30.9300C14—H140.9300
C4—C51.382 (3)
C7—N1—N2115.49 (14)N1—C7—H7119.5
C8—N2—N1119.98 (14)C1—C7—H7119.5
C8—N2—H2122.6 (18)O1—C8—N2121.20 (16)
N1—N2—H2117.1 (18)O1—C8—C9122.47 (16)
C12—O2—H2A109.5N2—C8—C9116.33 (14)
C2—C1—C6117.17 (16)C10—C9—C14117.80 (15)
C2—C1—C7121.73 (15)C10—C9—C8124.10 (15)
C6—C1—C7121.09 (16)C14—C9—C8118.08 (14)
C3—C2—C1122.21 (16)C11—C10—C9121.24 (16)
C3—C2—Cl1117.13 (14)C11—C10—H10119.4
C1—C2—Cl1120.66 (14)C9—C10—H10119.4
C4—C3—C2118.28 (17)C10—C11—C12120.19 (15)
C4—C3—H3120.9C10—C11—H11119.9
C2—C3—H3120.9C12—C11—H11119.9
C3—C4—C5121.92 (16)O2—C12—C13117.99 (16)
C3—C4—Cl2117.99 (14)O2—C12—C11122.74 (15)
C5—C4—Cl2120.08 (14)C13—C12—C11119.26 (16)
C6—C5—C4118.79 (16)C14—C13—C12120.10 (16)
C6—C5—H5120.6C14—C13—H13120.0
C4—C5—H5120.6C12—C13—H13120.0
C5—C6—C1121.61 (17)C13—C14—C9121.41 (15)
C5—C6—H6119.2C13—C14—H14119.3
C1—C6—H6119.2C9—C14—H14119.3
N1—C7—C1120.95 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···Cl2i0.89 (1)2.85 (1)3.7228 (16)167 (2)
O2—H2A···O1ii0.821.972.7624 (19)162

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5726).

References

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