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

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ISSN: 2056-9890

N′-[(1E)-1-(5-Chloro-2-hy­droxy­phen­yl)propyl­­idene]-4-meth­oxy­benzohydrazide

aDepartment of Material Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China, and bDepartment of Architecture and Mechanical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
*Correspondence e-mail: tsucjg@163.com

(Received 29 November 2009; accepted 9 December 2009; online 16 December 2009)

The title compound, C17H17ClN2O3, has a trans conformation about the C=N double bond and an intra­molecular O—H⋯N occurs. The crystal structure is stabilized by inter­molecular N—H⋯O hydrogen bonds.

Related literature

For further details of the chemistry of the title compound, see Carcelli et al. (1995[Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43-62.]); Salem (1998[Salem, A. A. (1998). Microchem. J. 60, 51-66.]).

[Scheme 1]

Experimental

Crystal data
  • C17H17ClN2O3

  • Mr = 332.78

  • Monoclinic, P 21

  • a = 8.6313 (13) Å

  • b = 4.9373 (8) Å

  • c = 19.610 (3) Å

  • β = 102.359 (3)°

  • V = 816.3 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.25 mm−1

  • T = 295 K

  • 0.25 × 0.17 × 0.12 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003[Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, WI, USA.]) Tmin = 0.940, Tmax = 0.971

  • 4350 measured reflections

  • 2837 independent reflections

  • 2047 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.098

  • S = 1.05

  • 2837 reflections

  • 209 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.13 e Å−3

  • Δρmin = −0.19 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1207 Friedel pairs

  • Flack parameter: 0.13 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N2 0.82 1.81 2.526 (3) 145
N1—H1A⋯O2i 0.86 2.23 2.934 (3) 140
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The chemistry of aroylhydrazones continues to attract attention due to their coordination ability to metal ions (Salem, 1998) and their biological activity (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=N2 double bond (Fig. 1). The dihedral angle between the two benzene rings is 3.0 (2)°. The crystal structure is stabilized by intramolecular O—H···N and intermolecular N—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).

Experimental top

4-methoxybenzohydrazide (0.01 mol,1.66 g) was dissolved in anhydrous ethanol (50 ml), and 1-(5-chloro-2-hydroxyphenyl)propan-1-one (0.01 mol, 1.84 g) was added. The reaction mixture was refluxed for 4 h with stirring, then the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 87%). The compound (1.0 mmol, 0.33 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 showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Packing diagram showing intramolecular O—H···N and intermolecular N—H···O hydrogen bonds (dashed lines).
N'-[(1E)-1-(5-Chloro-2-hydroxyphenyl)propylidene]- 4-methoxybenzohydrazide top
Crystal data top
C17H17ClN2O3F(000) = 348
Mr = 332.78Dx = 1.354 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 982 reflections
a = 8.6313 (13) Åθ = 2.8–21.4°
b = 4.9373 (8) ŵ = 0.25 mm1
c = 19.610 (3) ÅT = 295 K
β = 102.359 (3)°Block, colourless
V = 816.3 (2) Å30.25 × 0.17 × 0.12 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2837 independent reflections
Radiation source: fine-focus sealed tube2047 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 25.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 107
Tmin = 0.940, Tmax = 0.971k = 55
4350 measured reflectionsl = 1523
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0334P)2 + 0.0867P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2837 reflectionsΔρmax = 0.13 e Å3
209 parametersΔρmin = 0.19 e Å3
1 restraintAbsolute structure: Flack (1983), 1207 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.13 (9)
Crystal data top
C17H17ClN2O3V = 816.3 (2) Å3
Mr = 332.78Z = 2
Monoclinic, P21Mo Kα radiation
a = 8.6313 (13) ŵ = 0.25 mm1
b = 4.9373 (8) ÅT = 295 K
c = 19.610 (3) Å0.25 × 0.17 × 0.12 mm
β = 102.359 (3)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
2837 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2047 reflections with I > 2σ(I)
Tmin = 0.940, Tmax = 0.971Rint = 0.024
4350 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.098Δρmax = 0.13 e Å3
S = 1.05Δρmin = 0.19 e Å3
2837 reflectionsAbsolute structure: Flack (1983), 1207 Friedel pairs
209 parametersAbsolute structure parameter: 0.13 (9)
1 restraint
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
Cl10.70397 (10)0.5956 (2)0.50973 (4)0.0773 (3)
O10.5785 (2)0.0599 (5)0.75880 (12)0.0668 (6)
H10.50500.13020.77270.100*
O20.2166 (3)0.0098 (4)0.82097 (12)0.0690 (7)
O30.3408 (3)0.4662 (5)0.95022 (12)0.0740 (7)
N10.2158 (3)0.4370 (5)0.78114 (13)0.0541 (7)
H1A0.17330.59530.77630.065*
N20.3433 (3)0.3712 (5)0.75179 (13)0.0528 (7)
C10.6042 (4)0.1967 (6)0.70286 (16)0.0529 (8)
C20.5080 (3)0.4145 (6)0.67236 (15)0.0451 (7)
C30.5434 (3)0.5345 (7)0.61244 (14)0.0494 (8)
H30.48140.67710.59090.059*
C40.6678 (4)0.4446 (7)0.58540 (16)0.0552 (9)
C50.7620 (4)0.2322 (8)0.61561 (19)0.0635 (9)
H50.84540.17140.59650.076*
C60.7307 (3)0.1117 (8)0.67442 (18)0.0639 (9)
H60.79510.02890.69560.077*
C70.3708 (3)0.5104 (6)0.69966 (15)0.0452 (7)
C80.1611 (4)0.2390 (7)0.81801 (16)0.0520 (8)
C90.0293 (3)0.3162 (6)0.85165 (14)0.0445 (7)
C100.0777 (4)0.5202 (7)0.82750 (16)0.0574 (9)
H100.06420.62300.78950.069*
C110.2041 (3)0.5764 (7)0.85793 (15)0.0587 (8)
H110.27620.71190.84010.070*
C120.2215 (4)0.4274 (7)0.91544 (15)0.0525 (8)
C130.1146 (4)0.2243 (7)0.94116 (16)0.0577 (9)
H130.12640.12510.98000.069*
C140.0089 (4)0.1689 (6)0.90945 (15)0.0544 (8)
H140.07990.03100.92680.065*
C150.2677 (3)0.7379 (7)0.66588 (15)0.0536 (8)
H15A0.33000.86090.64400.064*
H15B0.22830.83800.70120.064*
C160.1279 (4)0.6325 (11)0.61111 (19)0.0939 (13)
H16A0.16650.54440.57440.141*
H16B0.06080.78130.59210.141*
H16C0.06840.50560.63230.141*
C170.4560 (4)0.6733 (9)0.9258 (2)0.0895 (13)
H17A0.40430.84640.92890.134*
H17B0.53420.67420.95400.134*
H17C0.50650.63770.87800.134*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0774 (6)0.0948 (7)0.0677 (5)0.0054 (6)0.0335 (4)0.0015 (6)
O10.0718 (15)0.0543 (16)0.0764 (14)0.0118 (13)0.0205 (12)0.0138 (14)
O20.1008 (18)0.0361 (15)0.0827 (16)0.0085 (12)0.0477 (15)0.0034 (12)
O30.0694 (15)0.085 (2)0.0769 (16)0.0074 (14)0.0363 (13)0.0030 (14)
N10.0677 (17)0.0358 (15)0.0667 (16)0.0042 (13)0.0319 (14)0.0035 (13)
N20.0639 (17)0.0403 (16)0.0606 (16)0.0001 (13)0.0278 (14)0.0000 (14)
C10.0542 (19)0.041 (2)0.062 (2)0.0043 (16)0.0091 (17)0.0025 (17)
C20.0453 (17)0.0380 (17)0.0522 (18)0.0049 (14)0.0108 (14)0.0051 (16)
C30.0473 (17)0.050 (2)0.0519 (17)0.0014 (16)0.0116 (14)0.0026 (16)
C40.0522 (18)0.059 (2)0.0562 (19)0.0078 (18)0.0162 (16)0.0090 (18)
C50.0491 (19)0.056 (2)0.089 (3)0.0005 (19)0.0211 (19)0.013 (2)
C60.0515 (18)0.052 (2)0.087 (2)0.0091 (18)0.0129 (17)0.004 (2)
C70.0491 (17)0.0347 (17)0.0529 (18)0.0037 (14)0.0134 (15)0.0061 (15)
C80.069 (2)0.0380 (19)0.053 (2)0.0046 (18)0.0224 (17)0.0020 (16)
C90.0575 (19)0.0341 (17)0.0447 (18)0.0021 (15)0.0169 (15)0.0039 (14)
C100.069 (2)0.053 (2)0.0545 (18)0.0021 (18)0.0208 (16)0.0090 (17)
C110.0565 (18)0.057 (2)0.0637 (19)0.007 (2)0.0151 (16)0.001 (2)
C120.0558 (19)0.055 (2)0.0492 (18)0.0047 (18)0.0173 (16)0.0069 (18)
C130.072 (2)0.053 (2)0.0514 (19)0.0018 (19)0.0227 (17)0.0089 (17)
C140.069 (2)0.046 (2)0.0505 (18)0.0060 (16)0.0188 (16)0.0054 (16)
C150.057 (2)0.0478 (19)0.062 (2)0.0037 (17)0.0244 (17)0.0041 (17)
C160.056 (2)0.113 (4)0.106 (3)0.006 (2)0.004 (2)0.010 (3)
C170.074 (3)0.099 (4)0.104 (3)0.013 (3)0.039 (2)0.002 (3)
Geometric parameters (Å, º) top
Cl1—C41.747 (3)C8—C91.481 (4)
O1—C11.346 (3)C9—C101.380 (4)
O1—H10.8200C9—C141.389 (4)
O2—C81.225 (4)C10—C111.379 (4)
O3—C121.364 (3)C10—H100.9300
O3—C171.435 (4)C11—C121.381 (4)
N1—C81.359 (4)C11—H110.9300
N1—N21.385 (3)C12—C131.383 (4)
N1—H1A0.8600C13—C141.372 (4)
N2—C71.295 (3)C13—H130.9300
C1—C61.393 (4)C14—H140.9300
C1—C21.411 (4)C15—C161.525 (4)
C2—C31.407 (4)C15—H15A0.9700
C2—C71.478 (4)C15—H15B0.9700
C3—C41.369 (4)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.381 (5)C16—H16C0.9600
C5—C61.375 (5)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—H60.9300C17—H17C0.9600
C7—C151.497 (4)
C1—O1—H1109.5C11—C10—C9122.1 (3)
C12—O3—C17118.4 (3)C11—C10—H10118.9
C8—N1—N2116.7 (2)C9—C10—H10118.9
C8—N1—H1A121.6C10—C11—C12118.7 (3)
N2—N1—H1A121.6C10—C11—H11120.6
C7—N2—N1120.0 (3)C12—C11—H11120.6
O1—C1—C6117.1 (3)O3—C12—C11124.0 (3)
O1—C1—C2122.9 (3)O3—C12—C13115.8 (3)
C6—C1—C2120.0 (3)C11—C12—C13120.2 (3)
C3—C2—C1117.5 (3)C14—C13—C12120.1 (3)
C3—C2—C7120.2 (3)C14—C13—H13119.9
C1—C2—C7122.3 (3)C12—C13—H13119.9
C4—C3—C2121.1 (3)C13—C14—C9120.8 (3)
C4—C3—H3119.5C13—C14—H14119.6
C2—C3—H3119.5C9—C14—H14119.6
C3—C4—C5121.2 (3)C7—C15—C16111.2 (3)
C3—C4—Cl1119.2 (3)C7—C15—H15A109.4
C5—C4—Cl1119.5 (3)C16—C15—H15A109.4
C6—C5—C4119.0 (3)C7—C15—H15B109.4
C6—C5—H5120.5C16—C15—H15B109.4
C4—C5—H5120.5H15A—C15—H15B108.0
C5—C6—C1121.2 (3)C15—C16—H16A109.5
C5—C6—H6119.4C15—C16—H16B109.5
C1—C6—H6119.4H16A—C16—H16B109.5
N2—C7—C2114.3 (3)C15—C16—H16C109.5
N2—C7—C15123.8 (3)H16A—C16—H16C109.5
C2—C7—C15121.8 (3)H16B—C16—H16C109.5
O2—C8—N1120.8 (3)O3—C17—H17A109.5
O2—C8—C9123.1 (3)O3—C17—H17B109.5
N1—C8—C9116.0 (3)H17A—C17—H17B109.5
C10—C9—C14118.0 (3)O3—C17—H17C109.5
C10—C9—C8123.8 (3)H17A—C17—H17C109.5
C14—C9—C8118.1 (3)H17B—C17—H17C109.5
C8—N1—N2—C7158.5 (3)N2—N1—C8—O24.4 (5)
O1—C1—C2—C3177.6 (3)N2—N1—C8—C9177.4 (3)
C6—C1—C2—C31.3 (4)O2—C8—C9—C10151.6 (3)
O1—C1—C2—C70.1 (4)N1—C8—C9—C1026.5 (4)
C6—C1—C2—C7179.0 (3)O2—C8—C9—C1426.0 (5)
C1—C2—C3—C40.7 (4)N1—C8—C9—C14155.8 (3)
C7—C2—C3—C4178.5 (3)C14—C9—C10—C111.4 (4)
C2—C3—C4—C50.5 (5)C8—C9—C10—C11176.3 (3)
C2—C3—C4—Cl1178.6 (2)C9—C10—C11—C121.6 (5)
C3—C4—C5—C60.8 (5)C17—O3—C12—C110.3 (5)
Cl1—C4—C5—C6178.8 (3)C17—O3—C12—C13179.7 (3)
C4—C5—C6—C11.3 (5)C10—C11—C12—O3179.4 (3)
O1—C1—C6—C5177.4 (3)C10—C11—C12—C130.7 (5)
C2—C1—C6—C51.6 (5)O3—C12—C13—C14179.6 (3)
N1—N2—C7—C2178.6 (2)C11—C12—C13—C140.3 (5)
N1—N2—C7—C152.6 (4)C12—C13—C14—C90.5 (5)
C3—C2—C7—N2175.1 (3)C10—C9—C14—C130.3 (4)
C1—C2—C7—N22.6 (4)C8—C9—C14—C13177.5 (3)
C3—C2—C7—C151.0 (4)N2—C7—C15—C1684.3 (4)
C1—C2—C7—C15178.7 (3)C2—C7—C15—C1691.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.812.526 (3)145
N1—H1A···O2i0.862.232.934 (3)140
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H17ClN2O3
Mr332.78
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)8.6313 (13), 4.9373 (8), 19.610 (3)
β (°) 102.359 (3)
V3)816.3 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.25 × 0.17 × 0.12
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.940, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
4350, 2837, 2047
Rint0.024
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.098, 1.05
No. of reflections2837
No. of parameters209
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.19
Absolute structureFlack (1983), 1207 Friedel pairs
Absolute structure parameter0.13 (9)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.812.526 (3)144.7
N1—H1A···O2i0.862.232.934 (3)139.5
Symmetry code: (i) x, y+1, z.
 

Acknowledgements

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

References

First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCarcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43–62.  CrossRef CAS PubMed Web of Science Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSalem, A. A. (1998). Microchem. J. 60, 51–66.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, WI, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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