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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o197.
Published online 2007 December 6. doi:  10.1107/S160053680706357X
PMCID: PMC2915260

2-Hydr­oxy-N′-[(1Z)-1-(2-hydr­oxy-5-methyl­phen­yl)-2-methyl­propyl­idene]benzohydrazide

Abstract

The title compound, C18H20N2O3, adopts a cis conformation with respect to the C=N double bond. The crystal structure is stabilized by intra­molecular N—H(...)O and inter­molecular O—H(...)O hydrogen bonds.

Related literature

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

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Object name is e-64-0o197-scheme1.jpg

Experimental

Crystal data

  • C18H20N2O3
  • M r = 312.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o197-efi1.jpg
  • a = 11.2144 (11) Å
  • b = 11.2887 (11) Å
  • c = 13.6535 (13) Å
  • β = 107.000 (2)°
  • V = 1653.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 273 (2) K
  • 0.25 × 0.22 × 0.16 mm

Data collection

  • Bruker APEX2 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.987, T max = 0.991
  • 8523 measured reflections
  • 2924 independent reflections
  • 2094 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.139
  • S = 1.00
  • 2924 reflections
  • 210 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 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: SHELXS97 (Sheldrick, 1997a [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a [triangle]); molecular graphics: SHELXTL (Sheldrick, 1997b [triangle]); 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/S160053680706357X/pk2070sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706357X/pk2070Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

The chemistry of aroylhydrazones continues to attract much attention due to their ability to coordinate 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 cis conformation with respect to the C8=N2 double bond (Fig. 1). The dihedral angle between the two benzene rings is 75.01 (6)°. The crystal structure is stabilized by intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (Table 1. and Fig. 2).

Experimental

2-hydroxybenzohydrazide (0.01 mol,1.52 g) was dissolved in anhydrous ethanol (50 ml) and 1-(2-hydroxy-5-methylphenyl)-2-methylpropan-1-one (0.01 mol, 1.78 g) was added. The reaction mixture was refluxed for 6 h with stirring, and the resulting precipitate was collected by filtration, washed several times with ethanol and dried in vacuo (yield 85%). The compound (1.0 mmol, 0.31 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

All H atoms were positioned geometrically and treated as riding on their parent atoms, with CH(methyl) = 0.96 Å, C—H(tertiary) = 0.98 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, Ctertiary, N).

Figures

Fig. 1.
The molecular structure of the title compound showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A packing diagram showing intramolecular N—H···O and intermolecular O—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C18H20N2O3F000 = 664
Mr = 312.36Dx = 1.255 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2019 reflections
a = 11.2144 (11) Åθ = 2.6–23.2º
b = 11.2887 (11) ŵ = 0.09 mm1
c = 13.6535 (13) ÅT = 273 (2) K
β = 107.000 (2)ºBlock, yellow
V = 1653.0 (3) Å30.25 × 0.22 × 0.16 mm
Z = 4

Data collection

Bruker APEX2 CCD area-detector diffractometer2924 independent reflections
Radiation source: fine-focus sealed tube2094 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 273(2) Kθmax = 25.1º
[var phi] and ω scansθmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −13→10
Tmin = 0.987, Tmax = 0.991k = −12→13
8523 measured reflectionsl = −10→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.0879P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
2924 reflectionsΔρmax = 0.20 e Å3
210 parametersΔρmin = −0.15 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
O10.14313 (13)0.32510 (11)0.31013 (11)0.0609 (4)
H10.15000.39650.32150.091*
O20.01561 (11)0.20180 (13)−0.04931 (10)0.0629 (4)
H20.04610.2149−0.09600.094*
O3−0.20731 (11)0.03822 (11)0.10448 (9)0.0555 (4)
N1−0.01360 (13)0.10594 (12)0.11865 (10)0.0445 (4)
H1A0.03460.14420.09100.053*
N20.03470 (14)0.05414 (12)0.21453 (11)0.0444 (4)
C10.21322 (16)0.29390 (14)0.24792 (13)0.0426 (4)
C20.21798 (15)0.17485 (15)0.22370 (12)0.0397 (4)
C30.28605 (16)0.14187 (17)0.15787 (14)0.0496 (5)
H30.28920.06230.14120.060*
C40.34956 (16)0.22417 (19)0.11622 (14)0.0546 (5)
C50.34352 (18)0.34066 (19)0.14234 (14)0.0566 (5)
H50.38570.39720.11560.068*
C60.27685 (18)0.37622 (17)0.20703 (14)0.0553 (5)
H60.27440.45600.22350.066*
C70.4215 (2)0.1856 (2)0.04319 (17)0.0788 (7)
H7A0.47350.24950.03370.118*
H7B0.36400.1644−0.02160.118*
H7C0.47250.11840.07130.118*
C80.14484 (16)0.08723 (14)0.26466 (13)0.0416 (4)
C90.20075 (18)0.03997 (16)0.37216 (14)0.0538 (5)
H90.21790.10890.41780.065*
C100.1119 (2)−0.0383 (2)0.40763 (17)0.0856 (8)
H10A0.03600.00420.40180.128*
H10B0.1495−0.06050.47770.128*
H10C0.0938−0.10810.36580.128*
C110.3253 (2)−0.0202 (2)0.38364 (17)0.0832 (7)
H11A0.3138−0.08530.33660.125*
H11B0.3584−0.04900.45240.125*
H11C0.38240.03570.36920.125*
C12−0.13535 (15)0.09610 (14)0.06947 (13)0.0399 (4)
C13−0.18372 (15)0.16196 (14)−0.02863 (12)0.0394 (4)
C14−0.11049 (17)0.21255 (15)−0.08482 (13)0.0443 (4)
C15−0.1663 (2)0.27366 (17)−0.17470 (15)0.0580 (5)
H15−0.11750.3059−0.21250.070*
C16−0.2935 (2)0.28657 (18)−0.20782 (16)0.0655 (6)
H16−0.33010.3283−0.26780.079*
C17−0.3677 (2)0.23870 (19)−0.15361 (16)0.0633 (6)
H17−0.45380.2483−0.17620.076*
C18−0.31253 (17)0.17651 (16)−0.06546 (15)0.0522 (5)
H18−0.36270.1431−0.02930.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0832 (10)0.0437 (7)0.0734 (9)0.0020 (7)0.0506 (8)−0.0056 (7)
O20.0526 (8)0.0929 (11)0.0496 (8)−0.0065 (7)0.0248 (7)0.0118 (7)
O30.0500 (8)0.0617 (8)0.0590 (8)−0.0089 (6)0.0224 (7)0.0137 (6)
N10.0446 (8)0.0515 (9)0.0388 (8)−0.0079 (6)0.0144 (7)0.0083 (7)
N20.0531 (9)0.0425 (8)0.0390 (8)−0.0005 (7)0.0159 (7)0.0044 (6)
C10.0462 (10)0.0433 (10)0.0424 (10)0.0036 (8)0.0193 (8)−0.0023 (8)
C20.0377 (9)0.0448 (10)0.0356 (9)0.0011 (7)0.0091 (7)−0.0026 (7)
C30.0451 (10)0.0563 (11)0.0489 (11)−0.0003 (8)0.0159 (9)−0.0156 (9)
C40.0395 (10)0.0822 (15)0.0439 (11)−0.0058 (9)0.0150 (9)−0.0101 (10)
C50.0545 (12)0.0673 (13)0.0523 (12)−0.0135 (10)0.0222 (10)0.0019 (10)
C60.0665 (13)0.0441 (10)0.0600 (12)−0.0056 (9)0.0258 (10)−0.0020 (9)
C70.0599 (13)0.119 (2)0.0680 (15)−0.0099 (12)0.0356 (12)−0.0210 (13)
C80.0488 (10)0.0365 (9)0.0405 (10)0.0040 (8)0.0145 (8)−0.0015 (8)
C90.0671 (13)0.0478 (11)0.0421 (11)0.0050 (9)0.0090 (9)0.0029 (8)
C100.103 (2)0.0882 (18)0.0617 (14)−0.0075 (14)0.0178 (14)0.0322 (13)
C110.0838 (17)0.0863 (17)0.0682 (15)0.0305 (13)0.0047 (13)0.0085 (13)
C120.0441 (10)0.0372 (9)0.0424 (10)−0.0035 (7)0.0189 (8)−0.0023 (7)
C130.0462 (10)0.0373 (9)0.0374 (9)−0.0018 (7)0.0161 (8)−0.0043 (7)
C140.0482 (10)0.0467 (10)0.0395 (10)−0.0063 (8)0.0154 (8)−0.0023 (8)
C150.0756 (15)0.0597 (12)0.0397 (11)−0.0133 (10)0.0185 (10)0.0026 (9)
C160.0818 (16)0.0580 (13)0.0460 (12)−0.0033 (11)0.0021 (11)0.0042 (9)
C170.0544 (12)0.0653 (13)0.0603 (13)0.0054 (10)0.0012 (10)−0.0001 (11)
C180.0468 (11)0.0572 (11)0.0542 (12)−0.0003 (9)0.0172 (9)−0.0044 (10)

Geometric parameters (Å, °)

O1—C11.3615 (19)C7—H7C0.9600
O1—H10.8200C8—C91.515 (2)
O2—C141.360 (2)C9—C101.513 (3)
O2—H20.8200C9—C111.519 (3)
O3—C121.2377 (19)C9—H90.9800
N1—C121.338 (2)C10—H10A0.9600
N1—N21.3909 (19)C10—H10B0.9600
N1—H1A0.8600C10—H10C0.9600
N2—C81.280 (2)C11—H11A0.9600
C1—C61.385 (2)C11—H11B0.9600
C1—C21.389 (2)C11—H11C0.9600
C2—C31.389 (2)C12—C131.489 (2)
C2—C81.494 (2)C13—C181.393 (2)
C3—C41.389 (3)C13—C141.399 (2)
C3—H30.9300C14—C151.387 (3)
C4—C51.369 (3)C15—C161.372 (3)
C4—C71.518 (2)C15—H150.9300
C5—C61.373 (3)C16—C171.376 (3)
C5—H50.9300C16—H160.9300
C6—H60.9300C17—C181.374 (3)
C7—H7A0.9600C17—H170.9300
C7—H7B0.9600C18—H180.9300
C1—O1—H1109.5C10—C9—H9106.6
C14—O2—H2109.5C8—C9—H9106.6
C12—N1—N2119.78 (13)C11—C9—H9106.6
C12—N1—H1A120.1C9—C10—H10A109.5
N2—N1—H1A120.1C9—C10—H10B109.5
C8—N2—N1115.46 (14)H10A—C10—H10B109.5
O1—C1—C6122.51 (15)C9—C10—H10C109.5
O1—C1—C2117.92 (15)H10A—C10—H10C109.5
C6—C1—C2119.56 (16)H10B—C10—H10C109.5
C1—C2—C3118.68 (16)C9—C11—H11A109.5
C1—C2—C8119.21 (14)C9—C11—H11B109.5
C3—C2—C8122.03 (15)H11A—C11—H11B109.5
C2—C3—C4122.00 (18)C9—C11—H11C109.5
C2—C3—H3119.0H11A—C11—H11C109.5
C4—C3—H3119.0H11B—C11—H11C109.5
C5—C4—C3117.72 (16)O3—C12—N1122.33 (15)
C5—C4—C7121.53 (18)O3—C12—C13120.26 (15)
C3—C4—C7120.74 (19)N1—C12—C13117.38 (13)
C4—C5—C6121.73 (17)C18—C13—C14117.82 (16)
C4—C5—H5119.1C18—C13—C12116.76 (14)
C6—C5—H5119.1C14—C13—C12125.40 (15)
C5—C6—C1120.31 (18)O2—C14—C15120.87 (16)
C5—C6—H6119.8O2—C14—C13118.95 (15)
C1—C6—H6119.8C15—C14—C13120.18 (17)
C4—C7—H7A109.5C16—C15—C14120.07 (18)
C4—C7—H7B109.5C16—C15—H15120.0
H7A—C7—H7B109.5C14—C15—H15120.0
C4—C7—H7C109.5C15—C16—C17121.00 (19)
H7A—C7—H7C109.5C15—C16—H16119.5
H7B—C7—H7C109.5C17—C16—H16119.5
N2—C8—C2122.85 (15)C18—C17—C16118.89 (19)
N2—C8—C9118.46 (15)C18—C17—H17120.6
C2—C8—C9118.62 (15)C16—C17—H17120.6
C10—C9—C8113.01 (17)C17—C18—C13122.03 (18)
C10—C9—C11112.20 (18)C17—C18—H18119.0
C8—C9—C11111.40 (16)C13—C18—H18119.0
C12—N1—N2—C8−166.53 (15)C2—C8—C9—C10174.27 (17)
O1—C1—C2—C3178.11 (16)N2—C8—C9—C11124.62 (19)
C6—C1—C2—C3−0.6 (3)C2—C8—C9—C11−58.3 (2)
O1—C1—C2—C81.2 (2)N2—N1—C12—O3−2.8 (2)
C6—C1—C2—C8−177.50 (16)N2—N1—C12—C13174.85 (14)
C1—C2—C3—C40.3 (3)O3—C12—C13—C1813.7 (2)
C8—C2—C3—C4177.10 (16)N1—C12—C13—C18−163.97 (15)
C2—C3—C4—C50.2 (3)O3—C12—C13—C14−168.03 (16)
C2—C3—C4—C7−179.04 (17)N1—C12—C13—C1414.3 (2)
C3—C4—C5—C6−0.3 (3)C18—C13—C14—O2178.59 (16)
C7—C4—C5—C6178.90 (19)C12—C13—C14—O20.4 (2)
C4—C5—C6—C10.0 (3)C18—C13—C14—C15−0.7 (2)
O1—C1—C6—C5−178.17 (18)C12—C13—C14—C15−178.97 (16)
C2—C1—C6—C50.5 (3)O2—C14—C15—C16−178.11 (17)
N1—N2—C8—C2−0.4 (2)C13—C14—C15—C161.2 (3)
N1—N2—C8—C9176.55 (14)C14—C15—C16—C17−0.6 (3)
C1—C2—C8—N293.6 (2)C15—C16—C17—C18−0.5 (3)
C3—C2—C8—N2−83.1 (2)C16—C17—C18—C130.9 (3)
C1—C2—C8—C9−83.3 (2)C14—C13—C18—C17−0.3 (3)
C3—C2—C8—C999.94 (19)C12—C13—C18—C17178.06 (17)
N2—C8—C9—C10−2.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.861.982.6413 (18)133
O2—H2···O1i0.821.962.7249 (17)155
O1—H1···O3ii0.821.902.6787 (18)158

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2070).

References

  • 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. [PubMed]
  • 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.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography