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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2872.
Published online 2009 October 28. doi:  10.1107/S1600536809043530
PMCID: PMC2971161

N′-Diphenyl­methyl­ene-2-hydroxy­benzohydrazide

Abstract

The title compound, C20H16N2O2, was synthesized by the reaction of 2-hydroxy­benzohydrazide with diphenyl­methanone. The dihedral angle between the phenyl rings is 76.28 (11)°. The amino H atom is involved in an intra­molecular N—H(...)O hydrogen bond. In the crystal structure, the hydr­oxy groups and carbonyl O atoms form inter­molecular O—H(...)O hydrogen bonds, which link the mol­ecules into chains running along the b axis.

Related literature

For general background to Schiff bases in coordination chemistry, see: Garnovskii et al. (1993 [triangle]); Musie et al. (2001 [triangle]); Paul et al. (2002 [triangle]); Anderson et al. (1997 [triangle]). For a related structure, see Ji & Shi (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2872-scheme1.jpg

Experimental

Crystal data

  • C20H16N2O2
  • M r = 316.35
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2872-efi1.jpg
  • a = 15.4057 (18) Å
  • b = 12.5179 (15) Å
  • c = 8.8445 (10) Å
  • β = 103.777 (2)°
  • V = 1656.6 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 K
  • 0.15 × 0.12 × 0.10 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.988, T max = 0.992
  • 8538 measured reflections
  • 2934 independent reflections
  • 1910 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.126
  • S = 1.05
  • 2934 reflections
  • 219 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043530/cv2634sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043530/cv2634Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y06–2–08).

supplementary crystallographic information

Comment

In recent years, a number of Schiff-bases have been investigated in terms of their coordination chemistry (Garnovskii et al., 1993; Musie et al., 2001; Paul et al., 2002) and biological systems (Anderson et al., 1997). In order to search for new Schiff-bases with higher bioactivity, the title compound, (I), was synthesized and its crystal structure determined.

In (I) (Fig. 1), the bond lengths and angles are in a good agreement with those observed in the related compound (Ji & Shi, 2008). Intramolecular O—H···N hydrogen bond (Table 1) influences the molecular conformation. In the crystal structure, the molecules are linked into infinite chains by O—H···O hydrogen bonds (Table 1, Fig. 2).

Experimental

The title compound was synthesized by the reaction of 2-hydroxy-benzoic acid hydrazide(1 mmol, 152.2 mg) with diphenyl-methanone (1 mmol, 182.2 mg) in ethanol (20 ml) under reflux conditions (348 K) for 5 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After six days, colourless crystals suitable for X-ray diffraction study were obtained.

Refinement

All H atoms were placed in idealized positions (C—H = 0.93— 0.97 Å, N—H = 0.86 Å, O—H = 0.82 Å) and refined as riding atoms, with Uiso(H) = 1.2 or 1.5Ueq of the parent atom.

Figures

Fig. 1.
The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
A portion of the crystal packing showing the hydrogen-bonded (dashed lines) chain.

Crystal data

C20H16N2O2F(000) = 664
Mr = 316.35Dx = 1.268 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1519 reflections
a = 15.4057 (18) Åθ = 2.7–21.7°
b = 12.5179 (15) ŵ = 0.08 mm1
c = 8.8445 (10) ÅT = 295 K
β = 103.777 (2)°Block, colourless
V = 1656.6 (3) Å30.15 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer2934 independent reflections
Radiation source: fine-focus sealed tube1910 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] and ω scansθmax = 25.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −18→16
Tmin = 0.988, Tmax = 0.992k = −14→13
8538 measured reflectionsl = −10→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.126w = 1/[σ2(Fo2) + (0.0607P)2 + 0.0637P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2934 reflectionsΔρmax = 0.15 e Å3
219 parametersΔρmin = −0.15 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0070 (15)

Special details

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)

xyzUiso*/Ueq
O10.00834 (9)0.02500 (10)0.30160 (15)0.0574 (4)
H1−0.0088−0.03590.31250.086*
O20.06286 (9)0.32928 (10)0.16995 (15)0.0555 (4)
N10.12496 (10)0.18665 (12)0.30963 (18)0.0502 (4)
H1A0.12220.11970.32970.060*
N20.19612 (10)0.24715 (12)0.38673 (19)0.0528 (4)
C80.26326 (12)0.19876 (15)0.4739 (2)0.0482 (5)
C2−0.01536 (12)0.16611 (13)0.1159 (2)0.0422 (4)
C70.05922 (12)0.23391 (14)0.2017 (2)0.0434 (5)
C90.27034 (12)0.08062 (15)0.4971 (2)0.0484 (5)
C6−0.10938 (12)0.00942 (15)0.0696 (2)0.0502 (5)
H6−0.1254−0.05700.10160.060*
C1−0.03865 (12)0.06532 (14)0.1631 (2)0.0431 (5)
C150.34002 (12)0.26687 (16)0.5508 (2)0.0520 (5)
C3−0.06406 (13)0.20669 (15)−0.0252 (2)0.0521 (5)
H3−0.04960.2738−0.05700.063*
C160.34477 (13)0.37350 (16)0.5095 (2)0.0586 (6)
H160.29840.40330.43430.070*
C5−0.15573 (13)0.05148 (16)−0.0693 (2)0.0577 (5)
H5−0.20290.0133−0.13090.069*
C170.41724 (15)0.43560 (19)0.5786 (3)0.0684 (6)
H170.41930.50680.54990.082*
C200.41002 (13)0.22566 (19)0.6647 (3)0.0659 (6)
H200.40810.15480.69510.079*
C4−0.13280 (14)0.15061 (16)−0.1188 (2)0.0601 (6)
H4−0.16360.1785−0.21390.072*
C100.32717 (14)0.02240 (18)0.4281 (2)0.0635 (6)
H100.36090.05700.36850.076*
C140.22226 (14)0.02769 (16)0.5863 (3)0.0620 (6)
H140.18410.06580.63360.074*
C120.28481 (17)−0.13853 (18)0.5365 (3)0.0733 (7)
H120.2891−0.21230.54890.088*
C130.23000 (16)−0.08149 (18)0.6065 (3)0.0746 (7)
H130.1977−0.11630.66820.089*
C180.48636 (16)0.3929 (2)0.6896 (3)0.0767 (7)
H180.53560.43470.73480.092*
C110.33363 (16)−0.08721 (19)0.4479 (3)0.0739 (7)
H110.3713−0.12620.40080.089*
C190.48253 (15)0.2882 (2)0.7335 (3)0.0791 (7)
H190.52880.25930.80980.095*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0607 (9)0.0447 (8)0.0559 (9)−0.0078 (7)−0.0078 (7)0.0078 (7)
O20.0594 (9)0.0384 (7)0.0623 (9)−0.0028 (6)0.0021 (7)0.0022 (6)
N10.0429 (9)0.0383 (8)0.0611 (10)−0.0037 (7)−0.0043 (8)0.0002 (8)
N20.0446 (9)0.0491 (9)0.0586 (10)−0.0067 (8)0.0000 (8)−0.0011 (8)
C80.0404 (11)0.0523 (11)0.0488 (11)−0.0012 (9)0.0042 (9)0.0004 (9)
C20.0399 (10)0.0395 (10)0.0448 (11)0.0032 (8)0.0056 (8)−0.0019 (8)
C70.0413 (10)0.0396 (11)0.0472 (11)0.0028 (9)0.0059 (9)−0.0006 (9)
C90.0382 (10)0.0516 (11)0.0494 (12)0.0018 (9)−0.0011 (9)−0.0013 (9)
C60.0461 (11)0.0439 (11)0.0562 (12)−0.0032 (9)0.0038 (10)−0.0039 (9)
C10.0422 (10)0.0405 (10)0.0433 (11)0.0032 (8)0.0034 (9)−0.0025 (8)
C150.0426 (11)0.0608 (13)0.0500 (12)−0.0057 (10)0.0055 (9)−0.0017 (10)
C30.0526 (12)0.0480 (11)0.0514 (12)0.0015 (9)0.0038 (10)0.0028 (9)
C160.0492 (12)0.0623 (13)0.0614 (14)−0.0066 (11)0.0078 (10)0.0012 (11)
C50.0510 (12)0.0580 (13)0.0564 (13)−0.0049 (10)−0.0025 (10)−0.0116 (11)
C170.0616 (14)0.0704 (14)0.0731 (16)−0.0205 (12)0.0156 (13)−0.0029 (12)
C200.0542 (13)0.0691 (14)0.0652 (14)−0.0085 (11)−0.0041 (11)0.0014 (11)
C40.0604 (13)0.0600 (13)0.0493 (12)0.0007 (11)−0.0078 (10)0.0012 (10)
C100.0580 (14)0.0745 (15)0.0561 (13)0.0080 (12)0.0096 (11)−0.0011 (12)
C140.0535 (13)0.0533 (12)0.0791 (15)0.0034 (10)0.0157 (11)0.0031 (11)
C120.0687 (16)0.0562 (14)0.0826 (17)0.0063 (12)−0.0065 (14)−0.0007 (13)
C130.0647 (15)0.0598 (14)0.0981 (19)−0.0009 (12)0.0170 (14)0.0087 (13)
C180.0557 (15)0.0946 (19)0.0743 (16)−0.0265 (14)0.0043 (13)−0.0112 (14)
C110.0684 (16)0.0753 (16)0.0708 (16)0.0239 (13)0.0021 (13)−0.0180 (13)
C190.0538 (14)0.0948 (19)0.0756 (17)−0.0127 (13)−0.0108 (12)−0.0011 (14)

Geometric parameters (Å, °)

O1—C11.363 (2)C16—C171.378 (3)
O1—H10.8200C16—H160.9300
O2—C71.231 (2)C5—C41.389 (3)
N1—C71.352 (2)C5—H50.9300
N1—N21.373 (2)C17—C181.373 (3)
N1—H1A0.8600C17—H170.9300
N2—C81.285 (2)C20—C191.381 (3)
C8—C151.485 (3)C20—H200.9300
C8—C91.493 (3)C4—H40.9300
C2—C31.390 (3)C10—C111.384 (3)
C2—C11.402 (2)C10—H100.9300
C2—C71.483 (2)C14—C131.380 (3)
C9—C141.374 (3)C14—H140.9300
C9—C101.388 (3)C12—C131.362 (3)
C6—C51.371 (3)C12—C111.369 (3)
C6—C11.390 (3)C12—H120.9300
C6—H60.9300C13—H130.9300
C15—C201.388 (3)C18—C191.372 (3)
C15—C161.390 (3)C18—H180.9300
C3—C41.372 (3)C11—H110.9300
C3—H30.9300C19—H190.9300
C1—O1—H1109.5C6—C5—H5119.7
C7—N1—N2119.00 (15)C4—C5—H5119.7
C7—N1—H1A120.5C18—C17—C16120.4 (2)
N2—N1—H1A120.5C18—C17—H17119.8
C8—N2—N1118.12 (16)C16—C17—H17119.8
N2—C8—C15116.33 (17)C19—C20—C15121.1 (2)
N2—C8—C9124.85 (17)C19—C20—H20119.5
C15—C8—C9118.78 (16)C15—C20—H20119.5
C3—C2—C1118.30 (17)C3—C4—C5118.98 (19)
C3—C2—C7115.88 (16)C3—C4—H4120.5
C1—C2—C7125.80 (16)C5—C4—H4120.5
O2—C7—N1121.23 (17)C11—C10—C9119.9 (2)
O2—C7—C2120.69 (16)C11—C10—H10120.0
N1—C7—C2118.00 (16)C9—C10—H10120.0
C14—C9—C10118.84 (19)C9—C14—C13120.7 (2)
C14—C9—C8121.65 (17)C9—C14—H14119.7
C10—C9—C8119.51 (18)C13—C14—H14119.7
C5—C6—C1120.47 (18)C13—C12—C11119.9 (2)
C5—C6—H6119.8C13—C12—H12120.0
C1—C6—H6119.8C11—C12—H12120.0
O1—C1—C6121.44 (16)C12—C13—C14120.3 (2)
O1—C1—C2118.79 (16)C12—C13—H13119.9
C6—C1—C2119.76 (17)C14—C13—H13119.9
C20—C15—C16117.83 (19)C19—C18—C17119.7 (2)
C20—C15—C8121.03 (18)C19—C18—H18120.1
C16—C15—C8121.13 (18)C17—C18—H18120.1
C4—C3—C2121.93 (18)C12—C11—C10120.4 (2)
C4—C3—H3119.0C12—C11—H11119.8
C2—C3—H3119.0C10—C11—H11119.8
C17—C16—C15120.9 (2)C18—C19—C20120.1 (2)
C17—C16—H16119.6C18—C19—H19120.0
C15—C16—H16119.6C20—C19—H19120.0
C6—C5—C4120.55 (19)
C7—N1—N2—C8−171.19 (17)C9—C8—C15—C16167.06 (18)
N1—N2—C8—C15177.98 (15)C1—C2—C3—C4−0.7 (3)
N1—N2—C8—C90.5 (3)C7—C2—C3—C4177.72 (17)
N2—N1—C7—O21.2 (3)C20—C15—C16—C170.7 (3)
N2—N1—C7—C2177.88 (15)C8—C15—C16—C17−178.39 (18)
C3—C2—C7—O217.5 (3)C1—C6—C5—C4−0.1 (3)
C1—C2—C7—O2−164.16 (17)C15—C16—C17—C180.2 (3)
C3—C2—C7—N1−159.20 (16)C16—C15—C20—C19−0.7 (3)
C1—C2—C7—N119.1 (3)C8—C15—C20—C19178.36 (19)
N2—C8—C9—C14−73.8 (3)C2—C3—C4—C51.6 (3)
C15—C8—C9—C14108.8 (2)C6—C5—C4—C3−1.2 (3)
N2—C8—C9—C10106.6 (2)C14—C9—C10—C110.9 (3)
C15—C8—C9—C10−70.8 (2)C8—C9—C10—C11−179.48 (19)
C5—C6—C1—O1180.00 (17)C10—C9—C14—C13−0.3 (3)
C5—C6—C1—C20.9 (3)C8—C9—C14—C13−179.9 (2)
C3—C2—C1—O1−179.66 (16)C11—C12—C13—C141.1 (4)
C7—C2—C1—O12.1 (3)C9—C14—C13—C12−0.8 (4)
C3—C2—C1—C6−0.5 (3)C16—C17—C18—C19−1.0 (4)
C7—C2—C1—C6−178.80 (16)C13—C12—C11—C10−0.5 (4)
N2—C8—C15—C20170.39 (19)C9—C10—C11—C12−0.6 (3)
C9—C8—C15—C20−12.0 (3)C17—C18—C19—C201.0 (4)
N2—C8—C15—C16−10.6 (3)C15—C20—C19—C18−0.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.902.7204 (17)173
N1—H1A···O10.862.082.696 (2)128

Symmetry codes: (i) −x, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2634).

References

  • Anderson, O. P., Cour, A. L., Findeisen, M., Hennig, L., Simonsen, O., Taylor, L. & Toflund, H. (1997). J. Chem. Soc. Dalton Trans. pp. 111–120.
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Garnovskii, A. D., Nivorozhkin, A. L. & Minkin, V. I. (1993). Coord. Chem. Rev.126, 1–69.
  • Ji, N.-N. & Shi, Z.-Q. (2008). Acta Cryst. E64, o1918. [PMC free article] [PubMed]
  • Musie, G. T., Wei, M., Subramaniam, B. & Busch, D. H. (2001). Inorg. Chem 40, 3336–3341. [PubMed]
  • Paul, S., Barik, A. K., Peng, S. M. & Kar, S. K. (2002). Inorg. Chem.41, 5803–5809. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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