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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): o2482.
Published online 2010 September 4. doi:  10.1107/S1600536810035063
PMCID: PMC2983165

N′-(4-Hy­droxy­benzyl­idene)-2-methyl­benzohydrazide

Abstract

The title hydrazone compound, C15H14N2O2, was prepared by the condensation of 4-hy­droxy­benzaldehyde with 2-methyl­benzohydrazide in methanol. The dihedral angle between the two benzene rings is 42.3 (2)°. In the crystal structure, mol­ecules are linked by inter­molecular O—H(...)O, O—H(...)N and N—H(...)O hydrogen bonds, forming a three-dimensional framework.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 [triangle]); Pyta et al. (2010 [triangle]); Angelusiu et al. (2010 [triangle]); Fun et al. (2008 [triangle]); Singh & Singh (2010 [triangle]); Ahmad et al. (2010 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2482-scheme1.jpg

Experimental

Crystal data

  • C15H14N2O2
  • M r = 254.28
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2482-efi1.jpg
  • a = 7.6900 (15) Å
  • b = 11.701 (2) Å
  • c = 14.471 (3) Å
  • V = 1302.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.20 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.983, T max = 0.984
  • 10755 measured reflections
  • 1634 independent reflections
  • 1502 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.101
  • S = 1.12
  • 1634 reflections
  • 177 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [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/S1600536810035063/ci5176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035063/ci5176Isup2.hkl

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

Acknowledgments

Financial support from the Jiaying University research fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Hydrazone compounds have been received much attention in biological chemistry and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). In the present paper, the author reports the crystal structure of the title new hydrazone compound (Fig. 1).

In the title molecule, the dihedral angle between the two benzene rings is 42.3 (2)°. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8 and N1—N2—C8—C9 are 2.9 (2), 0.9 (2), and 0.2 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through O–H···O, O–H···N, and N–H···O intermolecular hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2).

Experimental

4-Hydroxybenzaldehyde (0.1 mmol, 12.2 mg) and 3-methylbenzohydrazide (0.1 mmol, 15.0 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless block-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

Refinement

Atom H2 was located in a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å [Uiso(H) = 0.08 Å2]. Other H atoms were constrained to ideal geometries, with C–H = 0.93–0.96 Å, O–H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(C15 and O1). In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Figures

Fig. 1.
The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Molecular packing of the title compound, with hydrogen bonds shown as dashed lines.

Crystal data

C15H14N2O2F(000) = 536
Mr = 254.28Dx = 1.297 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4917 reflections
a = 7.6900 (15) Åθ = 2.2–27.1°
b = 11.701 (2) ŵ = 0.09 mm1
c = 14.471 (3) ÅT = 298 K
V = 1302.1 (4) Å3Block, colourless
Z = 40.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer1634 independent reflections
Radiation source: fine-focus sealed tube1502 reflections with I > 2σ(I)
graphiteRint = 0.024
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.983, Tmax = 0.984k = −14→14
10755 measured reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.12w = 1/[σ2(Fo2) + (0.0604P)2 + 0.1042P] where P = (Fo2 + 2Fc2)/3
1634 reflections(Δ/σ)max = 0.001
177 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = −0.23 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N10.1045 (2)0.76789 (13)0.47260 (10)0.0442 (4)
N20.1260 (2)0.70443 (13)0.55210 (10)0.0433 (4)
O10.1276 (2)1.15917 (11)0.16838 (8)0.0439 (3)
H10.06601.13230.12750.066*
O20.0277 (2)0.54745 (11)0.47842 (8)0.0480 (4)
C10.1310 (2)0.94736 (15)0.39752 (11)0.0369 (4)
C20.0694 (2)0.90743 (16)0.31255 (12)0.0397 (4)
H2A0.02880.83280.30800.048*
C30.0675 (2)0.97611 (15)0.23590 (12)0.0391 (4)
H30.02640.94820.17990.047*
C40.1276 (2)1.08777 (15)0.24249 (11)0.0345 (4)
C50.1884 (3)1.12934 (16)0.32573 (13)0.0416 (4)
H50.22831.20420.33000.050*
C60.1899 (3)1.05962 (16)0.40250 (12)0.0427 (4)
H60.23091.08800.45840.051*
C70.1410 (3)0.87360 (15)0.47796 (12)0.0402 (4)
H70.17470.90430.53450.048*
C80.0859 (2)0.59215 (15)0.54852 (11)0.0375 (4)
C90.1113 (2)0.52835 (15)0.63685 (12)0.0389 (4)
C100.1715 (3)0.41533 (17)0.63644 (15)0.0483 (5)
C110.1871 (3)0.3609 (2)0.7213 (2)0.0631 (7)
H110.22860.28630.72290.076*
C120.1439 (3)0.4126 (3)0.80218 (18)0.0703 (8)
H120.15590.37320.85760.084*
C130.0828 (3)0.5227 (2)0.80235 (14)0.0649 (7)
H130.05190.55790.85760.078*
C140.0678 (3)0.5808 (2)0.71959 (13)0.0498 (5)
H140.02800.65590.71940.060*
C150.2224 (4)0.3530 (2)0.5498 (2)0.0763 (8)
H15A0.11960.33060.51670.114*
H15B0.28860.28630.56560.114*
H15C0.29150.40240.51160.114*
H20.190 (3)0.733 (2)0.5994 (13)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0618 (10)0.0404 (8)0.0303 (7)−0.0046 (8)−0.0064 (7)0.0072 (6)
N20.0622 (10)0.0384 (8)0.0294 (7)−0.0076 (8)−0.0103 (7)0.0068 (6)
O10.0610 (8)0.0385 (6)0.0322 (6)−0.0012 (6)−0.0033 (6)0.0082 (5)
O20.0697 (9)0.0413 (7)0.0329 (6)−0.0064 (7)−0.0078 (6)−0.0010 (6)
C10.0426 (9)0.0353 (8)0.0327 (8)0.0014 (8)−0.0021 (7)0.0036 (7)
C20.0499 (10)0.0322 (8)0.0371 (9)−0.0036 (8)−0.0030 (8)0.0023 (7)
C30.0485 (10)0.0373 (9)0.0316 (8)0.0001 (8)−0.0038 (7)−0.0014 (7)
C40.0380 (8)0.0335 (8)0.0319 (8)0.0054 (7)0.0010 (7)0.0054 (7)
C50.0537 (11)0.0304 (8)0.0407 (9)−0.0019 (8)−0.0045 (8)0.0012 (7)
C60.0566 (11)0.0393 (9)0.0322 (8)−0.0018 (9)−0.0088 (8)−0.0008 (8)
C70.0504 (10)0.0396 (9)0.0305 (8)−0.0009 (8)−0.0039 (8)0.0016 (8)
C80.0437 (9)0.0370 (8)0.0317 (8)−0.0007 (8)−0.0010 (7)0.0020 (7)
C90.0414 (9)0.0390 (9)0.0361 (8)−0.0069 (8)−0.0055 (8)0.0068 (7)
C100.0468 (11)0.0388 (9)0.0592 (12)−0.0054 (8)−0.0076 (9)0.0087 (9)
C110.0553 (13)0.0510 (12)0.0831 (17)−0.0073 (10)−0.0172 (13)0.0303 (13)
C120.0643 (14)0.0870 (18)0.0594 (14)−0.0195 (15)−0.0179 (11)0.0431 (14)
C130.0711 (15)0.0877 (19)0.0361 (10)−0.0117 (14)−0.0034 (10)0.0141 (11)
C140.0590 (12)0.0541 (11)0.0364 (9)−0.0040 (10)−0.0023 (9)0.0065 (9)
C150.092 (2)0.0484 (12)0.0880 (18)0.0146 (14)−0.0047 (17)−0.0092 (14)

Geometric parameters (Å, °)

N1—C71.271 (2)C6—H60.93
N1—N21.379 (2)C7—H70.93
N2—C81.350 (2)C8—C91.493 (2)
N2—H20.907 (10)C9—C141.387 (3)
O1—C41.3594 (19)C9—C101.401 (3)
O1—H10.82C10—C111.389 (3)
O2—C81.226 (2)C10—C151.503 (3)
C1—C61.391 (3)C11—C121.358 (4)
C1—C21.398 (2)C11—H110.93
C1—C71.451 (2)C12—C131.371 (4)
C2—C31.370 (2)C12—H120.93
C2—H2A0.93C13—C141.382 (3)
C3—C41.389 (3)C13—H130.93
C3—H30.93C14—H140.93
C4—C51.381 (2)C15—H15A0.96
C5—C61.378 (2)C15—H15B0.96
C5—H50.93C15—H15C0.96
C7—N1—N2116.54 (15)O2—C8—C9122.87 (16)
C8—N2—N1117.68 (14)N2—C8—C9115.07 (15)
C8—N2—H2120.6 (17)C14—C9—C10120.08 (17)
N1—N2—H2119.9 (17)C14—C9—C8119.10 (17)
C4—O1—H1109.5C10—C9—C8120.77 (17)
C6—C1—C2118.12 (15)C11—C10—C9117.2 (2)
C6—C1—C7120.18 (16)C11—C10—C15119.6 (2)
C2—C1—C7121.65 (16)C9—C10—C15123.19 (19)
C3—C2—C1121.31 (16)C12—C11—C10122.5 (2)
C3—C2—H2A119.3C12—C11—H11118.8
C1—C2—H2A119.3C10—C11—H11118.8
C2—C3—C4119.52 (16)C11—C12—C13120.2 (2)
C2—C3—H3120.2C11—C12—H12119.9
C4—C3—H3120.2C13—C12—H12119.9
O1—C4—C5118.15 (16)C12—C13—C14119.3 (2)
O1—C4—C3121.59 (15)C12—C13—H13120.3
C5—C4—C3120.26 (15)C14—C13—H13120.3
C6—C5—C4119.83 (16)C13—C14—C9120.7 (2)
C6—C5—H5120.1C13—C14—H14119.7
C4—C5—H5120.1C9—C14—H14119.7
C5—C6—C1120.96 (16)C10—C15—H15A109.5
C5—C6—H6119.5C10—C15—H15B109.5
C1—C6—H6119.5H15A—C15—H15B109.5
N1—C7—C1121.21 (16)C10—C15—H15C109.5
N1—C7—H7119.4H15A—C15—H15C109.5
C1—C7—H7119.4H15B—C15—H15C109.5
O2—C8—N2122.01 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.962.7657 (18)166
O1—H1···N1i0.822.522.995 (2)118
N2—H2···O1ii0.91 (1)2.14 (1)2.995 (2)158 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5176).

References

  • Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976. [PMC free article] [PubMed]
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