supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers buy article online

pk2040 scheme

Acta Cryst. (2007). E63, o4022    [ doi:10.1107/S1600536807043590 ]

N'-[(1E)-(5-Chloro-2-hydroxyphenyl)(phenyl)methylene]-4-methoxybenzohydrazide

J.-G. Chang and R.-D. Yang

Abstract top

The title compound, C21H17ClN2O3, displays a trans configuration with respect to the C=N double bond. The crystal structure is stabilized by intramolecular O-H...N and intermolecular C-H...O hydrogen bonds.

Comment top

The chemistry of aroylhydrazones continues to attract much attention due to their coordination ability to metal ions (Singh et al., 1982; Salem, 1998) and their biological activity (Singh et al., 1982; Carcelli et al., 1995). As an extension of work on the structural characterization of aroylhydrazone derivatives, the title compound was synthesized and its crystal structure is reported here.

The title molecule displays a trans conformation with respect to the C7=N1 double bond (Fig. 1). The three benzene rings, C1—C6 (A), C8—C13 (B) and C15—C20 (C), make dihedral angles of 74.21 (7) ° (A/B), 79.58 (7) ° (B/C) and 16.85 (12) ° (A/C). The crystal structure is stabilized by intramolecular N—H···O and intermolecular C—H···O hydrogen bonds (Table 1. and Fig. 2).

Related literature top

For further details of the chemistry of the title compound, see: Carcelli et al. (1995); Salem (1998); Singh et al. (1982).

Experimental top

4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (50 ml), and (5-chloro-2-hydroxyphenyl)(phenyl)methanone (0.01 mol, 2.32 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 81%). The compound (1.0 mmol,0.38 g) was dissolved in dimethylformamide (20 ml) and kept at room temperature for 45 d to obtain yellow single crystals suitable for X-ray diffraction.

Refinement top

All H atoms were positioned geometrically and treated as riding on their parent atoms, with CMe—H = 0.96 Å, CAr—H = 0.93 Å, O—H = 0.82 Å, and N—H = 0.86 Å and with Uiso(H) = 1.5Ueq(CMe, O) and 1.2Ueq(CAr, 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, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound, viewed roughly along the b axis. Dashed lines show intra-and intermolecular hydrogen bonds.
N'-[(1E)-(5-chloro-2-hydroxyphenyl)(phenyl)methylene]-4- methoxybenzohydrazide top
Crystal data top
C21H17ClN2O3F000 = 792
Mr = 380.82Dx = 1.360 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3423 reflections
a = 9.2861 (19) Åθ = 2.4–21.3º
b = 13.026 (3) ŵ = 0.23 mm−1
c = 15.722 (3) ÅT = 273 (2) K
β = 102.089 (8)ºPlate, yellow
V = 1859.6 (7) Å30.33 × 0.24 × 0.13 mm
Z = 4
Data collection top
Bruker APEX II CCD area-detector
diffractometer		3259 independent reflections
Radiation source: fine-focus sealed tube2262 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.045
T = 273(2) Kθmax = 25.0º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −10→11
Tmin = 0.945, Tmax = 0.966k = −15→15
16781 measured reflectionsl = −18→18
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043  w = 1/[σ2(Fo2) + (0.0962P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.150(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.20 e Å−3
3259 reflectionsΔρmin = −0.26 e Å−3
247 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (3)
Secondary atom site location: difference Fourier map
Crystal data top
C21H17ClN2O3V = 1859.6 (7) Å3
Mr = 380.82Z = 4
Monoclinic, P21/nMo Kα
a = 9.2861 (19) ŵ = 0.23 mm−1
b = 13.026 (3) ÅT = 273 (2) K
c = 15.722 (3) Å0.33 × 0.24 × 0.13 mm
β = 102.089 (8)º
Data collection top
Bruker APEX II CCD area-detector
diffractometer		3259 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		2262 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.966Rint = 0.045
16781 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043247 parameters
wR(F2) = 0.150H-atom parameters constrained
S = 1.00Δρmax = 0.20 e Å−3
3259 reflectionsΔρmin = −0.26 e Å−3
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 > 2σ(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
Cl10.13352 (7)0.88139 (5)0.18144 (5)0.0801 (3)
O10.6354 (2)0.60874 (13)0.30330 (11)0.0705 (5)
H10.69750.61340.27330.106*
O20.99011 (18)0.55710 (13)0.21902 (10)0.0674 (5)
O31.35103 (16)0.55585 (13)−0.08113 (10)0.0647 (5)
N10.74992 (19)0.67796 (14)0.17801 (11)0.0530 (5)
N20.85754 (19)0.67454 (14)0.13064 (12)0.0566 (5)
H210.85260.71460.08660.068*
C10.2845 (2)0.80152 (17)0.21698 (15)0.0570 (6)
C20.3986 (2)0.80150 (16)0.17394 (14)0.0533 (5)
H20.39480.84490.12660.064*
C30.5204 (2)0.73755 (15)0.19997 (13)0.0471 (5)
C40.5222 (3)0.67327 (16)0.27222 (14)0.0538 (5)
C50.4053 (3)0.67538 (19)0.31437 (15)0.0643 (7)
H50.40740.63270.36200.077*
C60.2874 (3)0.7384 (2)0.28777 (15)0.0664 (7)
H60.21000.73880.31690.080*
C70.6397 (2)0.73889 (16)0.15167 (13)0.0473 (5)
C80.6309 (2)0.80770 (15)0.07446 (13)0.0458 (5)
C90.7175 (2)0.89464 (16)0.07990 (14)0.0557 (6)
H90.77890.91210.13250.067*
C100.7133 (3)0.95584 (18)0.00764 (15)0.0643 (6)
H100.77221.01410.01190.077*
C110.6227 (3)0.93109 (18)−0.07028 (15)0.0612 (6)
H110.62070.9719−0.11900.073*
C120.5354 (3)0.8458 (2)−0.07564 (15)0.0643 (6)
H120.47280.8294−0.12820.077*
C130.5392 (2)0.78388 (18)−0.00424 (13)0.0585 (6)
H130.47980.7258−0.00900.070*
C140.9726 (2)0.60810 (16)0.15275 (13)0.0492 (5)
C151.0706 (2)0.60199 (15)0.08952 (13)0.0472 (5)
C161.1987 (2)0.54446 (18)0.11171 (15)0.0592 (6)
H161.22300.51410.16640.071*
C171.2902 (2)0.53153 (19)0.05433 (15)0.0626 (6)
H171.37640.49360.07070.075*
C181.2549 (2)0.57464 (17)−0.02765 (13)0.0504 (5)
C191.1298 (2)0.63223 (18)−0.05077 (14)0.0603 (6)
H191.10590.6625−0.10550.072*
C201.0394 (3)0.64517 (19)0.00765 (15)0.0605 (6)
H200.95440.6844−0.00870.073*
C211.3176 (3)0.5988 (2)−0.16640 (15)0.0705 (7)
H21A1.22450.5729−0.19730.106*
H21B1.39310.5803−0.19690.106*
H21C1.31260.6722−0.16240.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0543 (4)0.0815 (5)0.1113 (6)0.0072 (3)0.0332 (4)−0.0043 (4)
O10.0758 (12)0.0759 (12)0.0649 (11)0.0089 (9)0.0260 (9)0.0189 (8)
O20.0651 (10)0.0873 (12)0.0523 (9)0.0141 (9)0.0184 (7)0.0135 (8)
O30.0530 (9)0.0840 (12)0.0633 (10)0.0063 (8)0.0263 (8)−0.0002 (8)
N10.0519 (10)0.0576 (11)0.0548 (10)0.0021 (9)0.0232 (8)−0.0006 (8)
N20.0537 (11)0.0623 (12)0.0605 (11)0.0105 (9)0.0269 (9)0.0088 (9)
C10.0490 (13)0.0548 (13)0.0726 (15)−0.0083 (10)0.0250 (11)−0.0100 (11)
C20.0540 (13)0.0506 (13)0.0604 (13)−0.0049 (10)0.0240 (10)−0.0018 (10)
C30.0490 (12)0.0449 (11)0.0510 (11)−0.0057 (9)0.0186 (9)−0.0040 (9)
C40.0599 (13)0.0514 (13)0.0534 (12)−0.0057 (11)0.0194 (10)−0.0013 (10)
C50.0748 (16)0.0673 (16)0.0582 (14)−0.0141 (13)0.0310 (12)0.0019 (11)
C60.0611 (15)0.0736 (16)0.0737 (16)−0.0130 (13)0.0355 (12)−0.0107 (13)
C70.0471 (12)0.0481 (12)0.0497 (11)−0.0017 (10)0.0166 (9)−0.0045 (9)
C80.0418 (11)0.0497 (12)0.0508 (12)0.0022 (9)0.0212 (9)−0.0018 (9)
C90.0558 (13)0.0575 (14)0.0541 (13)−0.0076 (11)0.0125 (10)−0.0019 (10)
C100.0713 (16)0.0550 (14)0.0705 (16)−0.0094 (12)0.0237 (12)0.0038 (11)
C110.0741 (16)0.0592 (14)0.0554 (13)0.0080 (13)0.0252 (12)0.0065 (11)
C120.0650 (15)0.0789 (16)0.0495 (13)−0.0035 (13)0.0131 (11)−0.0033 (11)
C130.0601 (14)0.0641 (14)0.0528 (13)−0.0151 (12)0.0155 (11)−0.0056 (11)
C140.0452 (12)0.0560 (13)0.0465 (12)−0.0004 (10)0.0094 (9)−0.0022 (9)
C150.0423 (11)0.0502 (12)0.0497 (12)−0.0001 (9)0.0107 (9)−0.0020 (9)
C160.0525 (13)0.0745 (15)0.0511 (12)0.0092 (12)0.0122 (10)0.0092 (11)
C170.0461 (12)0.0785 (16)0.0637 (14)0.0166 (12)0.0123 (10)0.0070 (12)
C180.0432 (12)0.0554 (13)0.0547 (13)−0.0034 (10)0.0153 (10)−0.0045 (10)
C190.0583 (14)0.0733 (15)0.0533 (13)0.0133 (12)0.0205 (11)0.0111 (11)
C200.0563 (13)0.0699 (15)0.0580 (13)0.0215 (12)0.0180 (11)0.0119 (11)
C210.0718 (16)0.0882 (18)0.0580 (15)−0.0049 (14)0.0285 (12)−0.0033 (12)
Geometric parameters (Å, °) top
Cl1—C11.741 (2)C9—C101.382 (3)
O1—C41.355 (3)C9—H90.9300
O1—H10.8200C10—C111.371 (3)
O2—C141.217 (2)C10—H100.9300
O3—C181.371 (3)C11—C121.368 (3)
O3—C211.426 (3)C11—H110.9300
N1—C71.293 (3)C12—C131.377 (3)
N1—N21.367 (2)C12—H120.9300
N2—C141.362 (3)C13—H130.9300
N2—H210.8600C14—C151.484 (3)
C1—C21.372 (3)C15—C201.379 (3)
C1—C61.379 (3)C15—C161.387 (3)
C2—C31.395 (3)C16—C171.373 (3)
C2—H20.9300C16—H160.9300
C3—C41.409 (3)C17—C181.381 (3)
C3—C71.468 (3)C17—H170.9300
C4—C51.385 (3)C18—C191.366 (3)
C5—C61.362 (3)C19—C201.378 (3)
C5—H50.9300C19—H190.9300
C6—H60.9300C20—H200.9300
C7—C81.497 (3)C21—H21A0.9600
C8—C91.381 (3)C21—H21B0.9600
C8—C131.382 (3)C21—H21C0.9600
C4—O1—H1109.5C12—C11—C10119.4 (2)
C18—O3—C21117.72 (18)C12—C11—H11120.3
C7—N1—N2117.75 (17)C10—C11—H11120.3
C14—N2—N1120.38 (17)C11—C12—C13120.8 (2)
C14—N2—H21119.8C11—C12—H12119.6
N1—N2—H21119.8C13—C12—H12119.6
C2—C1—C6120.7 (2)C12—C13—C8120.3 (2)
C2—C1—Cl1119.68 (19)C12—C13—H13119.9
C6—C1—Cl1119.60 (17)C8—C13—H13119.9
C1—C2—C3121.2 (2)O2—C14—N2121.46 (19)
C1—C2—H2119.4O2—C14—C15123.61 (19)
C3—C2—H2119.4N2—C14—C15114.92 (18)
C2—C3—C4117.59 (19)C20—C15—C16117.21 (19)
C2—C3—C7119.61 (18)C20—C15—C14124.38 (19)
C4—C3—C7122.79 (19)C16—C15—C14118.31 (18)
O1—C4—C5117.8 (2)C17—C16—C15121.1 (2)
O1—C4—C3122.5 (2)C17—C16—H16119.4
C5—C4—C3119.7 (2)C15—C16—H16119.4
C6—C5—C4121.7 (2)C16—C17—C18120.3 (2)
C6—C5—H5119.2C16—C17—H17119.8
C4—C5—H5119.2C18—C17—H17119.8
C5—C6—C1119.1 (2)C19—C18—O3124.16 (19)
C5—C6—H6120.5C19—C18—C17119.6 (2)
C1—C6—H6120.5O3—C18—C17116.23 (19)
N1—C7—C3117.34 (18)C18—C19—C20119.5 (2)
N1—C7—C8122.16 (18)C18—C19—H19120.2
C3—C7—C8120.49 (18)C20—C19—H19120.2
C9—C8—C13118.7 (2)C19—C20—C15122.2 (2)
C9—C8—C7120.57 (18)C19—C20—H20118.9
C13—C8—C7120.66 (18)C15—C20—H20118.9
C8—C9—C10120.4 (2)O3—C21—H21A109.5
C8—C9—H9119.8O3—C21—H21B109.5
C10—C9—H9119.8H21A—C21—H21B109.5
C11—C10—C9120.3 (2)O3—C21—H21C109.5
C11—C10—H10119.8H21A—C21—H21C109.5
C9—C10—H10119.8H21B—C21—H21C109.5
C7—N1—N2—C14−176.75 (18)C7—C8—C9—C10177.5 (2)
C6—C1—C2—C30.4 (3)C8—C9—C10—C110.2 (3)
Cl1—C1—C2—C3−179.18 (15)C9—C10—C11—C120.6 (4)
C1—C2—C3—C4−0.2 (3)C10—C11—C12—C13−1.0 (4)
C1—C2—C3—C7179.33 (19)C11—C12—C13—C80.5 (4)
C2—C3—C4—O1−179.54 (18)C9—C8—C13—C120.3 (3)
C7—C3—C4—O10.9 (3)C7—C8—C13—C12−177.8 (2)
C2—C3—C4—C50.0 (3)N1—N2—C14—O2−6.7 (3)
C7—C3—C4—C5−179.49 (19)N1—N2—C14—C15172.13 (17)
O1—C4—C5—C6179.6 (2)O2—C14—C15—C20168.4 (2)
C3—C4—C5—C60.0 (3)N2—C14—C15—C20−10.5 (3)
C4—C5—C6—C10.1 (4)O2—C14—C15—C16−7.9 (3)
C2—C1—C6—C5−0.3 (3)N2—C14—C15—C16173.28 (18)
Cl1—C1—C6—C5179.25 (17)C20—C15—C16—C170.1 (3)
N2—N1—C7—C3176.48 (17)C14—C15—C16—C17176.7 (2)
N2—N1—C7—C8−2.7 (3)C15—C16—C17—C18−1.0 (4)
C2—C3—C7—N1−179.70 (18)C21—O3—C18—C19−0.3 (3)
C4—C3—C7—N1−0.2 (3)C21—O3—C18—C17179.7 (2)
C2—C3—C7—C8−0.5 (3)C16—C17—C18—C191.4 (4)
C4—C3—C7—C8179.07 (18)C16—C17—C18—O3−178.6 (2)
N1—C7—C8—C9−74.2 (3)O3—C18—C19—C20179.1 (2)
C3—C7—C8—C9106.6 (2)C17—C18—C19—C20−1.0 (3)
N1—C7—C8—C13103.9 (2)C18—C19—C20—C150.1 (4)
C3—C7—C8—C13−75.3 (3)C16—C15—C20—C190.3 (4)
C13—C8—C9—C10−0.7 (3)C14—C15—C20—C19−176.0 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.589 (2)146
C11—H11···O2i0.932.603.287 (3)130
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.872.589 (2)146
C11—H11···O2i0.932.603.287 (3)130
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2.
Acknowledgements top

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

references
References top

Bruker (2005). APEX2 (Version 1.27) and SAINT (Version 7.12). Bruker AXS Inc., Madison, Wisconsin, USA.

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

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

Sheldrick, G. M. (1997a). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2003). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA.

Singh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77–84.