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

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(E)-4-Chloro-N′-[1-(4-hy­droxy­phenyl)­ethyl­idene]benzohydrazide

aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721007, People's Republic of China
*Correspondence e-mail: desuoyang@yahoo.com.cn

(Received 16 August 2008; accepted 21 August 2008; online 30 August 2008)

The mol­ecule of the title compound, C15H13ClN2O2, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 15.1 (3)°. A strong intra­molecular O—H⋯N hydrogen bond is observed. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains running along [101].

Related literature

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-S19.]). For related structures, see: Yang (2007[Yang, D.-S. (2007). J. Chem. Crystallogr. 37, 343-348.], 2008a[Yang, D.-S. (2008a). Acta Cryst. E64, o1758.],b[Yang, D.-S. (2008b). Acta Cryst. E64, o1759.]). For general background, see: Bernardo et al. (1996[Bernardo, K., Leppard, S., Robert, A., Commenges, G., Dahan, F. & Meunier, B. (1996). Inorg. Chem. 35, 387-396.]); Musie et al. (2001[Musie, G. T., Wei, M., Subramaniam, B. & Busch, D. H. (2001). Inorg. Chem. 40, 3336-3341.]); Paul et al. (2002[Paul, S., Barik, A. K., Peng, S. M. & Kar, S. K. (2002). Inorg. Chem. 41, 5803-5809.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13ClN2O2

  • Mr = 288.72

  • Monoclinic, P 21 /n

  • a = 7.241 (3) Å

  • b = 23.653 (4) Å

  • c = 8.744 (3) Å

  • β = 113.682 (3)°

  • V = 1371.5 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 298 (2) K

  • 0.32 × 0.30 × 0.28 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.915, Tmax = 0.925

  • 11286 measured reflections

  • 2961 independent reflections

  • 1543 reflections with I > 2σ(I)

  • Rint = 0.071

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.143

  • S = 0.99

  • 2961 reflections

  • 186 parameters

  • 1 restraint

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

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯N2 0.82 1.80 2.513 (3) 145
N1—H1⋯O1i 0.90 (1) 2.074 (11) 2.968 (3) 176 (3)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2002[Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SAINT and SMART. 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: SHELXL97.

Supporting information


Comment top

Schiff base compounds have been of great interest for a long time. These compounds play an important role in the development of coordination chemistry (Musie et al., 2001; Bernardo et al., 1996; Paul et al., 2002). Recently, we have reported a few Schiff base compounds (Yang, 2007, 2008a,b). As a further investigation of this work, the crystal structure of the title compound is reported here.

The molecule of the title compound displays a trans configuration with respect to the C?N double bond (Fig. 1). The dihedral angle between the two benzene rings is 15.1 (3)°. All the bond lengths are within normal ranges (Allen et al., 1987). The C8N2 bond length of 1.287 (3) Å conforms to the value for a double bond. The N1—C7 bond length of 1.355 (3) Å is intermediate between a C—N single bond and a C?N double bond, because of conjugation effects in the molecule. There is a strong intramolecular hydrogen bond between the hydroxyl hydrogen and N2.

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains running along the [1 0 1] direction (Fig. 2).

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Yang (2007, 2008a,b). For general background, see: Bernardo et al. (1996); Musie et al. (2001); Paul et al. (2002).

Experimental top

1-(2-Hydroxyphenyl)ethanone (0.1 mmol, 13.6 mg) and 4-chlorobenzohydrazide (0.1 mmol, 17.0 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature to give a clear colourless solution. Single crystals of the title compound were obtained by gradual evaporation of the solvent over a period of 12 d at room temperature.

Refinement top

Atom H1 was located in a difference Fourier map and refined isotropically, with N—H distance restrained to 0.90 (1) Å and with a Uiso value of 0.08 Å2. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with a O—H distance of 0.82 Å, C—H distances of 0.93–0.96 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O2 and C15).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

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. Molecular packing as viewed along the c axis. Hydrogen bonds are shown as dashed lines.
(E)-4-Chloro-N'-[1-(4-hydroxyphenyl)ethylidene]benzohydrazide top
Crystal data top
C15H13ClN2O2F(000) = 600
Mr = 288.72Dx = 1.398 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 872 reflections
a = 7.241 (3) Åθ = 2.6–24.5°
b = 23.653 (4) ŵ = 0.28 mm1
c = 8.744 (3) ÅT = 298 K
β = 113.682 (3)°Block, colourless
V = 1371.5 (8) Å30.32 × 0.30 × 0.28 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2961 independent reflections
Radiation source: fine-focus sealed tube1543 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.916, Tmax = 0.926k = 2930
11286 measured reflectionsl = 1011
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0561P)2]
where P = (Fo2 + 2Fc2)/3
2961 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 0.26 e Å3
1 restraintΔρmin = 0.22 e Å3
Crystal data top
C15H13ClN2O2V = 1371.5 (8) Å3
Mr = 288.72Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.241 (3) ŵ = 0.28 mm1
b = 23.653 (4) ÅT = 298 K
c = 8.744 (3) Å0.32 × 0.30 × 0.28 mm
β = 113.682 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2961 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
1543 reflections with I > 2σ(I)
Tmin = 0.916, Tmax = 0.926Rint = 0.071
11286 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0581 restraint
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.26 e Å3
2961 reflectionsΔρmin = 0.22 e Å3
186 parameters
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
Cl10.37849 (13)0.06661 (4)1.09548 (11)0.0828 (4)
O10.1545 (3)0.20127 (8)0.3759 (2)0.0617 (6)
O20.2459 (4)0.30219 (8)0.1123 (2)0.0631 (6)
H20.25240.28880.20080.095*
N10.3189 (3)0.27241 (9)0.5512 (3)0.0434 (6)
N20.3039 (3)0.30449 (9)0.4155 (3)0.0420 (6)
C10.2803 (4)0.18339 (11)0.6672 (3)0.0435 (7)
C20.2877 (4)0.20451 (11)0.8154 (3)0.0478 (7)
H2A0.27310.24320.82650.057*
C30.3166 (4)0.16914 (12)0.9483 (4)0.0524 (8)
H30.31970.18341.04830.063*
C40.3408 (4)0.11202 (12)0.9296 (4)0.0503 (8)
C50.3352 (4)0.08999 (12)0.7838 (4)0.0563 (8)
H50.35330.05140.77420.068*
C60.3026 (4)0.12538 (12)0.6515 (3)0.0502 (7)
H60.29520.11060.55060.060*
C70.2461 (4)0.21899 (11)0.5182 (3)0.0438 (7)
C80.3356 (4)0.35814 (11)0.4314 (3)0.0382 (6)
C90.3192 (4)0.38770 (10)0.2801 (3)0.0374 (6)
C100.2770 (4)0.35866 (11)0.1294 (3)0.0460 (7)
C110.2624 (5)0.38790 (14)0.0107 (4)0.0678 (9)
H110.23410.36840.10990.081*
C120.2887 (5)0.44553 (14)0.0070 (4)0.0739 (10)
H120.27940.46470.10270.089*
C130.3289 (5)0.47455 (13)0.1384 (4)0.0662 (9)
H130.34620.51360.14160.079*
C140.3432 (4)0.44635 (11)0.2775 (4)0.0520 (8)
H140.37020.46670.37500.062*
C150.3841 (4)0.38928 (11)0.5915 (3)0.0533 (8)
H15A0.32030.37080.65530.080*
H15B0.33570.42740.56790.080*
H15C0.52750.38960.65430.080*
H10.418 (3)0.2788 (12)0.651 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0724 (6)0.0858 (7)0.0841 (7)0.0001 (5)0.0252 (5)0.0420 (5)
O10.0699 (14)0.0514 (12)0.0387 (12)0.0031 (10)0.0045 (11)0.0021 (10)
O20.0910 (16)0.0491 (13)0.0491 (13)0.0110 (11)0.0281 (13)0.0078 (10)
N10.0459 (14)0.0396 (13)0.0356 (13)0.0033 (11)0.0068 (11)0.0045 (11)
N20.0423 (14)0.0440 (14)0.0352 (13)0.0002 (11)0.0109 (11)0.0046 (11)
C10.0350 (16)0.0387 (17)0.0471 (18)0.0031 (12)0.0064 (13)0.0007 (13)
C20.0458 (18)0.0406 (16)0.0527 (19)0.0054 (13)0.0152 (15)0.0022 (14)
C30.0468 (19)0.061 (2)0.0483 (19)0.0079 (15)0.0176 (15)0.0026 (15)
C40.0351 (16)0.055 (2)0.054 (2)0.0018 (14)0.0112 (14)0.0203 (15)
C50.0476 (19)0.0370 (17)0.075 (2)0.0006 (13)0.0151 (17)0.0109 (16)
C60.0485 (18)0.0444 (18)0.0493 (18)0.0050 (13)0.0109 (14)0.0002 (14)
C70.0409 (16)0.0411 (17)0.0418 (17)0.0016 (13)0.0086 (14)0.0030 (13)
C80.0313 (15)0.0397 (16)0.0386 (16)0.0016 (12)0.0088 (12)0.0008 (12)
C90.0321 (14)0.0415 (16)0.0361 (15)0.0031 (12)0.0109 (12)0.0035 (12)
C100.0499 (18)0.0441 (18)0.0441 (17)0.0026 (13)0.0190 (14)0.0020 (14)
C110.089 (3)0.073 (2)0.0403 (19)0.0044 (19)0.0249 (17)0.0029 (16)
C120.093 (3)0.069 (2)0.055 (2)0.005 (2)0.0241 (19)0.0206 (18)
C130.080 (2)0.050 (2)0.062 (2)0.0014 (17)0.0216 (19)0.0116 (17)
C140.061 (2)0.0421 (18)0.0490 (18)0.0039 (14)0.0184 (15)0.0048 (14)
C150.070 (2)0.0473 (18)0.0411 (17)0.0005 (15)0.0204 (15)0.0006 (14)
Geometric parameters (Å, º) top
Cl1—C41.736 (3)C5—H50.93
O1—C71.225 (3)C6—H60.93
O2—C101.353 (3)C8—C91.459 (3)
O2—H20.82C8—C151.493 (3)
N1—C71.355 (3)C9—C141.400 (3)
N1—N21.375 (3)C9—C101.406 (3)
N1—H10.896 (10)C10—C111.373 (4)
N2—C81.287 (3)C11—C121.375 (4)
C1—C21.370 (4)C11—H110.93
C1—C61.395 (4)C12—C131.369 (4)
C1—C71.486 (4)C12—H120.93
C2—C31.377 (4)C13—C141.354 (4)
C2—H2A0.93C13—H130.93
C3—C41.381 (4)C14—H140.93
C3—H30.93C15—H15A0.96
C4—C51.363 (4)C15—H15B0.96
C5—C61.369 (4)C15—H15C0.96
C10—O2—H2109.5N2—C8—C15123.5 (2)
C7—N1—N2116.2 (2)C9—C8—C15121.1 (2)
C7—N1—H1117 (2)C14—C9—C10116.8 (2)
N2—N1—H1120 (2)C14—C9—C8121.6 (2)
C8—N2—N1120.1 (2)C10—C9—C8121.6 (2)
C2—C1—C6119.3 (3)O2—C10—C11116.7 (3)
C2—C1—C7123.5 (2)O2—C10—C9123.3 (2)
C6—C1—C7117.1 (3)C11—C10—C9120.0 (3)
C1—C2—C3120.8 (3)C10—C11—C12121.2 (3)
C1—C2—H2A119.6C10—C11—H11119.4
C3—C2—H2A119.6C12—C11—H11119.4
C2—C3—C4118.6 (3)C13—C12—C11119.6 (3)
C2—C3—H3120.7C13—C12—H12120.2
C4—C3—H3120.7C11—C12—H12120.2
C5—C4—C3121.8 (3)C14—C13—C12119.9 (3)
C5—C4—Cl1118.7 (2)C14—C13—H13120.1
C3—C4—Cl1119.5 (2)C12—C13—H13120.1
C4—C5—C6119.1 (3)C13—C14—C9122.5 (3)
C4—C5—H5120.4C13—C14—H14118.7
C6—C5—H5120.4C9—C14—H14118.7
C5—C6—C1120.4 (3)C8—C15—H15A109.5
C5—C6—H6119.8C8—C15—H15B109.5
C1—C6—H6119.8H15A—C15—H15B109.5
O1—C7—N1122.7 (2)C8—C15—H15C109.5
O1—C7—C1121.9 (2)H15A—C15—H15C109.5
N1—C7—C1115.4 (2)H15B—C15—H15C109.5
N2—C8—C9115.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N20.821.802.513 (3)145
N1—H1···O1i0.90 (1)2.07 (1)2.968 (3)176 (3)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H13ClN2O2
Mr288.72
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)7.241 (3), 23.653 (4), 8.744 (3)
β (°) 113.682 (3)
V3)1371.5 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.32 × 0.30 × 0.28
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.916, 0.926
No. of measured, independent and
observed [I > 2σ(I)] reflections
11286, 2961, 1543
Rint0.071
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.144, 0.99
No. of reflections2961
No. of parameters186
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.26, 0.22

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N20.821.802.513 (3)145
N1—H1···O1i0.90 (1)2.074 (11)2.968 (3)176 (3)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

The author acknowledges Key Laboratory Construction Support from the Education Office of Shanxi Province (project No. 05JS43).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19.  CrossRef Web of Science Google Scholar
First citationBernardo, K., Leppard, S., Robert, A., Commenges, G., Dahan, F. & Meunier, B. (1996). Inorg. Chem. 35, 387–396.  CSD CrossRef PubMed CAS Web of Science Google Scholar
First citationBruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationMusie, G. T., Wei, M., Subramaniam, B. & Busch, D. H. (2001). Inorg. Chem. 40, 3336–3341.  Web of Science CrossRef PubMed CAS Google Scholar
First citationPaul, S., Barik, A. K., Peng, S. M. & Kar, S. K. (2002). Inorg. Chem. 41, 5803–5809.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYang, D.-S. (2007). J. Chem. Crystallogr. 37, 343–348.  Web of Science CSD CrossRef CAS Google Scholar
First citationYang, D.-S. (2008a). Acta Cryst. E64, o1758.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYang, D.-S. (2008b). Acta Cryst. E64, o1759.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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