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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1048
https://doi.org/10.1107/S1600536810012419

N′-(2,4-Di­chloro­benzyl­­idene)-2-hydr­­oxy-3-methyl­benzohydrazide

You-Yue Hana* and Qiu-Rong Zhaoa

aDepartment of Chemistry and Life Sciences, Chuzhou University, Chuzhou, Anhui 239000, People's Republic of China
*Correspondence e-mail: hanyouyue@126.com

(Received 30 March 2010; accepted 1 April 2010; online 10 April 2010)

In the title compound, C15H12Cl2N2O2, the dihedral angle between the two benzene rings is 6.3 (2)°. The mol­ecule adopts an E configuration with respect to the C=N bond. An intra­molecular O—H⋯O hydrogen bond is observed. In the crystal structure, the mol­ecules are linked through inter­molecular N—H⋯O and C—H⋯O hydrogen bonds to form chains running along [101].

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010[Patil, S. A., Naik, V. H., Kulkarni, A. D., Kamble, U., Bagihalli, G. B. & Badami, P. S. (2010). J. Coord. Chem. 63, 688-699.]); Cukurovali et al. (2006[Cukurovali, A., Yilmaz, I., Gur, S. & Kazaz, C. (2006). Eur. J. Med. Chem. 41, 201-207.]). For related structures, see: Mohd Lair et al. (2009[Mohd Lair, N., Mohd Ali, H. & Ng, S. W. (2009). Acta Cryst. E65, o190.]); Lin & Sang (2009[Lin, X.-S. & Sang, Y.-L. (2009). Acta Cryst. E65, o1650.]); Suleiman Gwaram et al. (2010[Suleiman Gwaram, N., Khaledi, H., Mohd Ali, H., Robinson, W. T. & Abdulla, M. A. (2010). Acta Cryst. E66, o721.]); Li & Ban (2009[Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o876.]); Lo & Ng (2009[Lo, K. M. & Ng, S. W. (2009). Acta Cryst. E65, o969.]); Ning & Xu (2009[Ning, J.-H. & Xu, X.-W. (2009). Acta Cryst. E65, o905-o906.]); Zhu et al. (2009[Zhu, C.-G., Wei, Y.-J. & Zhu, Q.-Y. (2009). Acta Cryst. E65, o85.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C15H12Cl2N2O2

  • Mr = 323.17

  • Monoclinic, P 21 /n

  • a = 7.137 (1) Å

  • b = 28.146 (2) Å

  • c = 8.130 (1) Å

  • β = 115.098 (1)°

  • V = 1478.9 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 298 K

  • 0.20 × 0.20 × 0.17 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.917, Tmax = 0.928

  • 8543 measured reflections

  • 3211 independent reflections

  • 2439 reflections with I > 2σ(I)

  • Rint = 0.080
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.130

  • S = 1.08

  • 3211 reflections

  • 195 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯O2 0.82 1.96 2.6689 (19) 144
N2—H2⋯O2i 0.90 (1) 2.13 (1) 2.9905 (19) 161 (2)
C7—H7⋯O2i 0.93 2.45 3.264 (2) 146
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT . Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810012419/ci5073sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012419/ci5073Isup2.hkl

checkCIF report


Comment top

Hydrazone compounds have been widely investigated for their biological properties (Patil et al., 2010; Cukurovali et al., 2006). Furthermore, the crystal structures of the hydrazone compounds have also attracted much attention in recent years (Mohd Lair et al., 2009; Lin & Sang, 2009; Suleiman Gwaram et al., 2010). In the present work, the title new hydrazone compound is reported.

In the title molecule (Fig. 1), the dihedral angle between the two benzene rings is 6.3 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular O—H···O hydrogen bond (Table 1) in the molecule. All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable to those observed in related structures (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

In the crystal structure, molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) to form chains running along the [101] (Fig. 2).

Related literature top

For the biological properties of hydrazone compounds, see: Patil et al. (2010); Cukurovali et al. (2006). For related structures, see: Mohd Lair et al. (2009); Lin & Sang (2009); Suleiman Gwaram et al. (2010); Li & Ban (2009); Lo & Ng (2009); Ning & Xu (2009); Zhu et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 2,4-dichlorobenzaldehyde (0.174 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 g, 1 mmol) in methanol (50 ml) was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, single crystals of the title compound, suitable for X-ray diffraction, were formed.

Refinement top

Atom H2 was located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. Other H atoms were positioned geometrically and refined using the riding-model approximation, with C–H = 0.93 or 0.96 Å, O–H = 0.82 Å, and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(methyl C and O).

Structure description top

Hydrazone compounds have been widely investigated for their biological properties (Patil et al., 2010; Cukurovali et al., 2006). Furthermore, the crystal structures of the hydrazone compounds have also attracted much attention in recent years (Mohd Lair et al., 2009; Lin & Sang, 2009; Suleiman Gwaram et al., 2010). In the present work, the title new hydrazone compound is reported.

In the title molecule (Fig. 1), the dihedral angle between the two benzene rings is 6.3 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular O—H···O hydrogen bond (Table 1) in the molecule. All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable to those observed in related structures (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

In the crystal structure, molecules are linked through intermolecular N—H···O and C—H···O hydrogen bonds (Table 1) to form chains running along the [101] (Fig. 2).

For the biological properties of hydrazone compounds, see: Patil et al. (2010); Cukurovali et al. (2006). For related structures, see: Mohd Lair et al. (2009); Lin & Sang (2009); Suleiman Gwaram et al. (2010); Li & Ban (2009); Lo & Ng (2009); Ning & Xu (2009); Zhu et al. (2009). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 30% probability displacement ellipsoids for non-H atoms. An intramolecular hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. The molecular packing of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines.
N'-(2,4-Dichlorobenzylidene)-2-hydroxy-3-methylbenzohydrazide top
Crystal data top
C15H12Cl2N2O2F(000) = 664
Mr = 323.17Dx = 1.451 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3312 reflections
a = 7.137 (1) Åθ = 2.7–26.7°
b = 28.146 (2) ŵ = 0.44 mm−1
c = 8.130 (1) ÅT = 298 K
β = 115.098 (1)°Block, colourless
V = 1478.9 (3) Å30.20 × 0.20 × 0.17 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer		3211 independent reflections
Radiation source: fine-focus sealed tube2439 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
ω scansθmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −7→9
Tmin = 0.917, Tmax = 0.928k = −35→29
8543 measured reflectionsl = −10→10
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.0634P)2 + 0.0199P]
where P = (Fo2 + 2Fc2)/3
3211 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.20 e Å−3
1 restraintΔρmin = −0.34 e Å−3
Crystal data top
C15H12Cl2N2O2V = 1478.9 (3) Å3
Mr = 323.17Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.137 (1) ŵ = 0.44 mm−1
b = 28.146 (2) ÅT = 298 K
c = 8.130 (1) Å0.20 × 0.20 × 0.17 mm
β = 115.098 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3211 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2439 reflections with I > 2σ(I)
Tmin = 0.917, Tmax = 0.928Rint = 0.080
8543 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0451 restraint
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.20 e Å−3
3211 reflectionsΔρmin = −0.34 e Å−3
195 parameters
Special details top

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) top
xyzUiso*/Ueq
Cl10.08171 (10)0.072034 (18)0.35298 (7)0.0675 (2)
Cl20.28271 (12)0.02969 (2)1.04608 (9)0.0896 (3)
N10.2165 (2)0.21754 (5)0.51447 (19)0.0456 (3)
N20.1732 (2)0.24652 (5)0.36590 (19)0.0461 (4)
O10.2584 (2)0.39071 (4)0.38436 (19)0.0607 (4)
H10.30240.37230.47060.091*
O20.3710 (2)0.30580 (5)0.54178 (17)0.0612 (4)
C10.1840 (3)0.13994 (6)0.6149 (2)0.0418 (4)
C20.1588 (3)0.09173 (6)0.5740 (2)0.0456 (4)
C30.1937 (3)0.05770 (7)0.7075 (3)0.0532 (5)
H30.18150.02550.67900.064*
C40.2466 (3)0.07250 (7)0.8822 (3)0.0564 (5)
C50.2684 (3)0.11985 (7)0.9281 (3)0.0571 (5)
H50.30250.12931.04700.068*
C60.2390 (3)0.15312 (7)0.7953 (2)0.0507 (4)
H60.25620.18510.82630.061*
C70.1512 (3)0.17531 (6)0.4737 (2)0.0447 (4)
H70.08140.16670.35220.054*
C80.2616 (3)0.28989 (6)0.3889 (2)0.0440 (4)
C90.2212 (2)0.31687 (6)0.2219 (2)0.0412 (4)
C100.2190 (3)0.36649 (6)0.2284 (2)0.0458 (4)
C110.1737 (3)0.39357 (7)0.0725 (3)0.0530 (5)
C120.1414 (3)0.36996 (7)−0.0855 (3)0.0598 (5)
H120.11240.3876−0.19020.072*
C130.1503 (3)0.32088 (8)−0.0946 (3)0.0595 (5)
H130.13060.3060−0.20280.071*
C140.1888 (3)0.29443 (6)0.0593 (2)0.0487 (4)
H140.19320.26150.05440.058*
C150.1625 (4)0.44689 (7)0.0806 (4)0.0719 (6)
H15A0.15340.4603−0.03120.108*
H15B0.28450.45860.17970.108*
H15C0.04250.45580.09830.108*
H20.077 (3)0.2377 (8)0.2565 (18)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1002 (5)0.0532 (3)0.0537 (3)−0.0007 (3)0.0369 (3)−0.0057 (2)
Cl20.1246 (6)0.0848 (5)0.0756 (4)0.0201 (4)0.0580 (4)0.0368 (3)
N10.0454 (8)0.0445 (8)0.0405 (7)−0.0003 (6)0.0122 (6)0.0052 (6)
N20.0480 (9)0.0424 (8)0.0379 (7)−0.0048 (6)0.0083 (6)0.0040 (6)
O10.0731 (10)0.0438 (7)0.0648 (9)−0.0015 (6)0.0290 (8)−0.0077 (6)
O20.0725 (9)0.0499 (8)0.0422 (7)−0.0099 (6)0.0060 (7)−0.0029 (6)
C10.0380 (9)0.0467 (9)0.0401 (9)0.0001 (7)0.0158 (7)0.0036 (7)
C20.0472 (10)0.0483 (10)0.0472 (9)0.0026 (7)0.0256 (8)0.0032 (7)
C30.0599 (12)0.0453 (10)0.0631 (12)0.0056 (8)0.0344 (10)0.0104 (9)
C40.0585 (12)0.0638 (13)0.0545 (11)0.0116 (9)0.0312 (10)0.0189 (9)
C50.0597 (12)0.0695 (13)0.0416 (9)0.0060 (9)0.0211 (9)0.0056 (9)
C60.0516 (11)0.0515 (11)0.0451 (10)−0.0009 (8)0.0168 (9)0.0011 (8)
C70.0437 (10)0.0457 (10)0.0409 (9)−0.0019 (7)0.0143 (8)0.0015 (7)
C80.0411 (9)0.0408 (9)0.0436 (9)0.0018 (7)0.0118 (8)0.0015 (7)
C90.0346 (8)0.0412 (9)0.0425 (9)−0.0015 (6)0.0111 (7)0.0013 (7)
C100.0369 (9)0.0419 (9)0.0550 (11)0.0006 (7)0.0159 (8)0.0032 (8)
C110.0398 (10)0.0487 (10)0.0666 (12)0.0021 (7)0.0188 (9)0.0103 (9)
C120.0507 (12)0.0641 (13)0.0593 (12)−0.0033 (9)0.0181 (10)0.0198 (10)
C130.0579 (12)0.0746 (14)0.0435 (10)−0.0112 (10)0.0191 (9)−0.0023 (9)
C140.0467 (10)0.0469 (10)0.0489 (10)−0.0041 (8)0.0167 (8)−0.0011 (8)
C150.0662 (14)0.0479 (12)0.0980 (17)0.0069 (9)0.0313 (13)0.0206 (11)
Geometric parameters (Å, º) top
Cl1—C21.7319 (18)C5—H50.93
Cl2—C41.7323 (18)C6—H60.93
N1—C71.268 (2)C7—H70.93
N1—N21.3795 (19)C8—C91.474 (2)
N2—C81.350 (2)C9—C141.393 (2)
N2—H20.898 (10)C9—C101.398 (2)
O1—C101.360 (2)C10—C111.394 (3)
O1—H10.82C11—C121.376 (3)
O2—C81.2376 (19)C11—C151.506 (3)
C1—C21.391 (3)C12—C131.386 (3)
C1—C61.398 (2)C12—H120.93
C1—C71.461 (2)C13—C141.379 (3)
C2—C31.389 (2)C13—H130.93
C3—C41.371 (3)C14—H140.93
C3—H30.93C15—H15A0.96
C4—C51.375 (3)C15—H15B0.96
C5—C61.376 (3)C15—H15C0.96
C7—N1—N2113.86 (14)O2—C8—C9122.17 (16)
C8—N2—N1119.69 (14)N2—C8—C9116.17 (14)
C8—N2—H2120.2 (15)C14—C9—C10119.26 (16)
N1—N2—H2119.8 (15)C14—C9—C8121.98 (16)
C10—O1—H1109.5C10—C9—C8118.75 (15)
C2—C1—C6117.41 (16)O1—C10—C11116.74 (17)
C2—C1—C7121.03 (15)O1—C10—C9122.35 (16)
C6—C1—C7121.56 (16)C11—C10—C9120.91 (17)
C3—C2—C1121.58 (17)C12—C11—C10117.83 (17)
C3—C2—Cl1117.58 (14)C12—C11—C15122.08 (19)
C1—C2—Cl1120.84 (13)C10—C11—C15120.09 (19)
C4—C3—C2118.68 (18)C11—C12—C13122.54 (18)
C4—C3—H3120.7C11—C12—H12118.7
C2—C3—H3120.7C13—C12—H12118.7
C3—C4—C5121.67 (17)C14—C13—C12119.04 (19)
C3—C4—Cl2118.12 (16)C14—C13—H13120.5
C5—C4—Cl2120.20 (15)C12—C13—H13120.5
C4—C5—C6119.02 (18)C13—C14—C9120.33 (18)
C4—C5—H5120.5C13—C14—H14119.8
C6—C5—H5120.5C9—C14—H14119.8
C5—C6—C1121.58 (17)C11—C15—H15A109.5
C5—C6—H6119.2C11—C15—H15B109.5
C1—C6—H6119.2H15A—C15—H15B109.5
N1—C7—C1120.98 (16)C11—C15—H15C109.5
N1—C7—H7119.5H15A—C15—H15C109.5
C1—C7—H7119.5H15B—C15—H15C109.5
O2—C8—N2121.66 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.962.6689 (19)144
N2—H2···O2i0.90 (1)2.13 (1)2.9905 (19)161 (2)
C7—H7···O2i0.932.453.264 (2)146
Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formulaC15H12Cl2N2O2
Mr323.17
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.137 (1), 28.146 (2), 8.130 (1)
β (°) 115.098 (1)
V (Å3)1478.9 (3)
Z4
Radiation typeMo Kα
µ (mm−1)0.44
Crystal size (mm)0.20 × 0.20 × 0.17
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.917, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections		8543, 3211, 2439
Rint0.080
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.130, 1.08
No. of reflections3211
No. of parameters195
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.20, −0.34

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.962.6689 (19)144
N2—H2···O2i0.90 (1)2.13 (1)2.9905 (19)161 (2)
C7—H7···O2i0.932.453.264 (2)146
Symmetry code: (i) x−1/2, −y+1/2, z−1/2.
 

Acknowledgements

This work was supported by the Applied Chemistry Key Subject of Anhui Province (grant No. 200802187 C). The authors thank Mr Gang Wu of Chuzhou University for his help with the crystal growth.

References

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ISSN: 2056-9890
Volume 66| Part 5| May 2010| Page o1048
https://doi.org/10.1107/S1600536810012419
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