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Acta Cryst. (2010). E66, o2620    [ doi:10.1107/S1600536810037293 ]

N'-[(1E)-1-(3,5-Dichloro-2-hydroxyphenyl)propylidene]-4-methoxybenzohydrazide monohydrate

C.-H. He, J.-P. Zhang and J.-G. Chang

Abstract top

The title compound, C17H16Cl2N2O3·H2O, displays a trans conformation with respect to the C=N double bond. The dihedral angle between the two benzene rings is 30.77 (5)° and there is one intramolecular N-H...O hydrogen bond. In the crystal, molecules are linked by hydrogen bonding to the water molecules of crystallization, which acts as both an acceptor and a donor, into a three-dimensional network.

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their ability to coordinate with metal ions (Salem, 1998) and their biological activity (Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives (Chang & Ji, 2007), the title compound, (I),was synthesized and its crystal structure is reported here.

(I) displays a trans conformation with respect to the C7=N1 double bond (Fig. 1). The N2-N1=C7-C6 torsion angle is -175.44 (18)°.The dihedral angle between the two benzene rings is 30.77 (molecules are linked into a three dimensional network by intermolecular N-H···O, O-H···O Hydrogen bonds involving the water molecule which acts as both a donor and an acceptor.( Table. 1, Fig. 1and Fig. 2).

Related literature top

For further details of the chemistry of the title compound, see: Carcelli et al. (1995); Salem (1998). For a related structure, see: Chang & Ji (2007).

Experimental top

4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (40 ml), and 1-(3,5-dichloro-2-hydroxyphenyl)propan-1-one (0.01 mol, 2.19 g) was added. The reaction mixture was refluxed for 6 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 82%). The compound (1.0 mmol, 0.37 g) was dissolved in dimethylformamide (15 ml) and kept at room temperature for 30 d to obtain colourless single crystals suitable for X-ray diffraction.

Refinement top

All H atoms were positioned geometrically and treated as riding on their parent atoms,with C—H(methyl) = 0.96 Å, C—H(methylene) = 0.97 Å,C—H(aromatic) = 0.93 Å, O—H = 0.82 Å, N—H =0.86 Å and with Uiso(H) =1.5Ueq(Cmethyl,O) and 1.2Ueq(Caromatic,Cmethylene,N).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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 compound (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.Dashed lines show intramolecular O–H···N hydrogen bonds.
[Figure 2] Fig. 2. Packing diagram of (I), showing intermolecular O—H···O and N—H···O hydrogen bonds with the water molecule (dashed lines).
N'-[(1E)-1-(3,5-Dichloro-2-hydroxyphenyl)propylidene]-4- methoxybenzohydrazide monohydrate top
Crystal data top
C17H16Cl2N2O3·H2OF(000) = 1600
Mr = 385.23Dx = 1.395 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2261 reflections
a = 32.925 (3) Åθ = 2.7–22.8°
b = 7.3733 (7) ŵ = 0.38 mm−1
c = 15.1252 (13) ÅT = 295 K
β = 92.319 (2)°Block, colourless
V = 3668.9 (6) Å30.21 × 0.16 × 0.11 mm
Z = 8
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3242 independent reflections
Radiation source: fine-focus sealed tube2320 reflections with I > 2σ(I)
graphiteRint = 0.027
φ and ω scansθmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −38→31
Tmin = 0.925, Tmax = 0.960k = −7→8
9328 measured reflectionsl = −17→18
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.0624P)2 + 2.1699P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3242 reflectionsΔρmax = 0.28 e Å−3
230 parametersΔρmin = −0.39 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0014 (2)
Crystal data top
C17H16Cl2N2O3·H2OV = 3668.9 (6) Å3
Mr = 385.23Z = 8
Monoclinic, C2/cMo Kα radiation
a = 32.925 (3) ŵ = 0.38 mm−1
b = 7.3733 (7) ÅT = 295 K
c = 15.1252 (13) Å0.21 × 0.16 × 0.11 mm
β = 92.319 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3242 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2320 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.960Rint = 0.027
9328 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.127Δρmax = 0.28 e Å−3
S = 1.01Δρmin = −0.39 e Å−3
3242 reflectionsAbsolute structure: ?
230 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
Cl10.90858 (2)0.20782 (14)0.56665 (4)0.0858 (3)
Cl20.96867 (2)0.10906 (15)0.90003 (5)0.0939 (4)
N10.78571 (6)0.0580 (3)0.76338 (12)0.0430 (5)
N20.74565 (5)0.0416 (3)0.78172 (11)0.0449 (5)
H20.73780.02010.83420.054*
O10.83142 (5)0.1268 (2)0.64024 (10)0.0538 (5)
H10.80970.11040.66350.081*
O20.73122 (5)0.0679 (2)0.63564 (10)0.0550 (5)
O30.55192 (6)0.1318 (3)0.76671 (15)0.0877 (7)
O40.28854 (6)0.0811 (2)0.04707 (10)0.0605 (5)
H180.28300.0895−0.00810.091*
H190.30500.16700.05970.091*
C10.86185 (7)0.1190 (3)0.70224 (14)0.0445 (6)
C20.90114 (8)0.1561 (4)0.67682 (15)0.0528 (6)
C30.93372 (8)0.1525 (4)0.73556 (18)0.0636 (7)
H30.95970.17860.71720.076*
C40.92734 (8)0.1095 (4)0.82283 (17)0.0596 (7)
C50.88941 (7)0.0692 (3)0.85008 (16)0.0503 (6)
H50.88600.03870.90900.060*
C60.85555 (7)0.0729 (3)0.79125 (14)0.0409 (5)
C70.81465 (7)0.0354 (3)0.82230 (14)0.0397 (5)
C80.80792 (7)−0.0152 (3)0.91630 (14)0.0437 (5)
H8A0.8310−0.08440.93940.052*
H8B0.7840−0.09160.91860.052*
C90.80230 (9)0.1511 (4)0.97375 (16)0.0606 (7)
H9A0.82750.21600.97990.091*
H9B0.79390.11411.03110.091*
H9C0.78190.22840.94660.091*
C100.71868 (7)0.0615 (3)0.71071 (14)0.0418 (5)
C110.67535 (7)0.0788 (3)0.72990 (14)0.0422 (5)
C120.66180 (7)0.1335 (3)0.81114 (15)0.0505 (6)
H120.68070.15690.85700.061*
C130.62131 (8)0.1540 (4)0.82595 (17)0.0584 (7)
H130.61300.19090.88120.070*
C140.59297 (8)0.1198 (4)0.75892 (19)0.0593 (7)
C150.60576 (8)0.0678 (4)0.67635 (18)0.0621 (7)
H150.58670.04580.63060.075*
C160.64623 (7)0.0488 (3)0.66187 (16)0.0522 (6)
H160.65450.01540.60610.063*
C170.53716 (10)0.1785 (6)0.8521 (2)0.1014 (12)
H17A0.54650.09030.89500.152*
H17B0.50800.18020.84910.152*
H17C0.54720.29620.86920.152*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0798 (6)0.1289 (8)0.0498 (4)−0.0187 (5)0.0173 (4)−0.0021 (4)
Cl20.0387 (4)0.1699 (10)0.0722 (5)0.0028 (4)−0.0099 (3)0.0112 (5)
N10.0393 (11)0.0532 (12)0.0363 (10)0.0011 (9)−0.0018 (8)0.0007 (9)
N20.0402 (11)0.0603 (13)0.0340 (10)−0.0005 (9)−0.0003 (8)0.0058 (9)
O10.0489 (10)0.0745 (12)0.0378 (9)−0.0036 (9)−0.0019 (7)0.0026 (8)
O20.0523 (10)0.0788 (12)0.0337 (9)0.0002 (9)−0.0012 (7)0.0023 (8)
O30.0422 (11)0.1199 (19)0.1009 (17)0.0046 (11)0.0012 (11)−0.0046 (14)
O40.0738 (12)0.0694 (12)0.0379 (9)−0.0159 (9)−0.0028 (8)0.0036 (8)
C10.0480 (14)0.0468 (13)0.0385 (12)0.0019 (11)−0.0019 (10)−0.0035 (10)
C20.0504 (15)0.0648 (16)0.0439 (13)0.0003 (12)0.0082 (11)−0.0045 (12)
C30.0432 (15)0.085 (2)0.0629 (17)0.0017 (13)0.0084 (13)−0.0052 (15)
C40.0411 (14)0.082 (2)0.0554 (15)0.0071 (13)−0.0029 (12)−0.0018 (14)
C50.0442 (14)0.0633 (16)0.0432 (13)0.0097 (11)−0.0017 (11)0.0019 (11)
C60.0415 (13)0.0423 (13)0.0388 (12)0.0050 (10)−0.0013 (9)−0.0020 (10)
C70.0445 (13)0.0384 (12)0.0359 (11)0.0038 (10)−0.0023 (10)−0.0016 (9)
C80.0425 (13)0.0489 (13)0.0395 (12)0.0017 (10)−0.0031 (10)0.0053 (10)
C90.0770 (18)0.0666 (17)0.0383 (13)−0.0001 (14)0.0055 (12)−0.0033 (12)
C100.0462 (13)0.0414 (13)0.0374 (13)−0.0004 (10)−0.0044 (10)0.0002 (10)
C110.0426 (13)0.0409 (12)0.0425 (12)−0.0026 (10)−0.0062 (10)0.0040 (10)
C120.0459 (14)0.0614 (16)0.0436 (13)0.0016 (12)−0.0049 (11)−0.0010 (11)
C130.0532 (16)0.0683 (18)0.0541 (15)0.0056 (13)0.0049 (13)0.0004 (13)
C140.0417 (14)0.0641 (17)0.0719 (18)0.0013 (12)0.0004 (13)0.0059 (14)
C150.0477 (16)0.0732 (19)0.0638 (17)−0.0041 (13)−0.0179 (13)−0.0016 (14)
C160.0525 (15)0.0557 (15)0.0476 (14)−0.0007 (12)−0.0073 (11)−0.0025 (11)
C170.0529 (19)0.139 (3)0.114 (3)0.009 (2)0.0225 (19)−0.006 (3)
Geometric parameters (Å, °) top
Cl1—C21.736 (2)C7—C81.495 (3)
Cl2—C41.757 (3)C8—C91.519 (3)
N1—C71.289 (3)C8—H8A0.9700
N1—N21.364 (3)C8—H8B0.9700
N2—C101.374 (3)C9—H9A0.9600
N2—H20.8600C9—H9B0.9600
O1—C11.346 (3)C9—H9C0.9600
O1—H10.8200C10—C111.473 (3)
O2—C101.225 (3)C11—C121.384 (3)
O3—C141.364 (3)C11—C161.395 (3)
O3—C171.440 (4)C12—C131.369 (3)
O4—H180.8499C12—H120.9300
O4—H190.8500C13—C141.373 (4)
C1—C21.392 (3)C13—H130.9300
C1—C61.412 (3)C14—C151.388 (4)
C2—C31.365 (3)C15—C161.366 (4)
C3—C41.382 (4)C15—H150.9300
C3—H30.9300C16—H160.9300
C4—C51.364 (3)C17—H17A0.9600
C5—C61.398 (3)C17—H17B0.9600
C5—H50.9300C17—H17C0.9600
C6—C71.470 (3)
C7—N1—N2122.80 (18)C8—C9—H9A109.5
N1—N2—C10115.55 (18)C8—C9—H9B109.5
N1—N2—H2122.2H9A—C9—H9B109.5
C10—N2—H2122.2C8—C9—H9C109.5
C1—O1—H1109.5H9A—C9—H9C109.5
C14—O3—C17117.7 (2)H9B—C9—H9C109.5
H18—O4—H19106.0O2—C10—N2119.8 (2)
O1—C1—C2118.2 (2)O2—C10—C11123.0 (2)
O1—C1—C6122.7 (2)N2—C10—C11117.13 (19)
C2—C1—C6119.0 (2)C12—C11—C16117.7 (2)
C3—C2—C1122.1 (2)C12—C11—C10123.3 (2)
C3—C2—Cl1119.4 (2)C16—C11—C10118.9 (2)
C1—C2—Cl1118.50 (18)C13—C12—C11121.9 (2)
C2—C3—C4118.7 (2)C13—C12—H12119.1
C2—C3—H3120.6C11—C12—H12119.1
C4—C3—H3120.6C12—C13—C14119.7 (2)
C5—C4—C3121.0 (2)C12—C13—H13120.1
C5—C4—Cl2119.5 (2)C14—C13—H13120.1
C3—C4—Cl2119.5 (2)O3—C14—C13124.8 (3)
C4—C5—C6121.3 (2)O3—C14—C15115.7 (2)
C4—C5—H5119.3C13—C14—C15119.5 (2)
C6—C5—H5119.3C16—C15—C14120.4 (2)
C5—C6—C1117.9 (2)C16—C15—H15119.8
C5—C6—C7120.7 (2)C14—C15—H15119.8
C1—C6—C7121.45 (19)C15—C16—C11120.7 (2)
N1—C7—C6114.57 (19)C15—C16—H16119.6
N1—C7—C8123.8 (2)C11—C16—H16119.6
C6—C7—C8121.57 (18)O3—C17—H17A109.5
C7—C8—C9111.64 (19)O3—C17—H17B109.5
C7—C8—H8A109.3H17A—C17—H17B109.5
C9—C8—H8A109.3O3—C17—H17C109.5
C7—C8—H8B109.3H17A—C17—H17C109.5
C9—C8—H8B109.3H17B—C17—H17C109.5
H8A—C8—H8B108.0
C7—N1—N2—C10−177.1 (2)C1—C6—C7—C8179.4 (2)
O1—C1—C2—C3179.5 (2)N1—C7—C8—C9−88.7 (3)
C6—C1—C2—C3−1.2 (4)C6—C7—C8—C988.0 (3)
O1—C1—C2—Cl1−0.7 (3)N1—N2—C10—O29.7 (3)
C6—C1—C2—Cl1178.64 (18)N1—N2—C10—C11−168.88 (19)
C1—C2—C3—C40.4 (4)O2—C10—C11—C12−157.1 (2)
Cl1—C2—C3—C4−179.4 (2)N2—C10—C11—C1221.4 (3)
C2—C3—C4—C50.7 (4)O2—C10—C11—C1619.2 (3)
C2—C3—C4—Cl2−178.6 (2)N2—C10—C11—C16−162.3 (2)
C3—C4—C5—C6−1.1 (4)C16—C11—C12—C131.4 (4)
Cl2—C4—C5—C6178.2 (2)C10—C11—C12—C13177.8 (2)
C4—C5—C6—C10.3 (4)C11—C12—C13—C140.0 (4)
C4—C5—C6—C7−177.8 (2)C17—O3—C14—C13−1.9 (4)
O1—C1—C6—C5−179.9 (2)C17—O3—C14—C15177.7 (3)
C2—C1—C6—C50.8 (3)C12—C13—C14—O3178.4 (2)
O1—C1—C6—C7−1.8 (3)C12—C13—C14—C15−1.1 (4)
C2—C1—C6—C7178.9 (2)O3—C14—C15—C16−178.9 (3)
N2—N1—C7—C6−175.44 (18)C13—C14—C15—C160.7 (4)
N2—N1—C7—C81.4 (3)C14—C15—C16—C110.8 (4)
C5—C6—C7—N1174.4 (2)C12—C11—C16—C15−1.9 (4)
C1—C6—C7—N1−3.6 (3)C10—C11—C16—C15−178.4 (2)
C5—C6—C7—C8−2.6 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.772.494 (2)146
N2—H2···O4i0.862.163.004 (2)168
O4—H18···O2ii0.851.972.815 (2)171
O4—H19···O1iii0.852.112.908 (2)155
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.772.494 (2)146
N2—H2···O4i0.862.163.004 (2)168
O4—H18···O2ii0.851.972.815 (2)171
O4—H19···O1iii0.852.112.908 (2)155
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2.
Acknowledgements top

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y05-2-09).

references
References top

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43–62.

Chang, J.-G. & Ji, C.-Y. (2007). Acta Cryst. E63, o3212.

Salem, A. A. (1998). Microchem. J. 60, 51–66.

Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.