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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2200.
Published online 2009 August 22. doi:  10.1107/S1600536809032449
PMCID: PMC2970121

N′-(2-Hydr­oxy-4-methoxy­benzyl­idene)-4-methoxy­benzohydrazide

Abstract

In the title compound, C16H16N2O4, the dihedral angle between the two benzene rings is 8.7 (2)°. The mol­ecule adopts an E configuration about the C=N bond, with an intra­molecular O—H(...)N hydrogen bond involving the hydr­oxy substituent and the hydrazide N atom. In the crystal structure, adjacent mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds, forming chains propagating in the b-axis direction.

Related literature

For related structures, see: Alhadi et al. (2008 [triangle]); Küçükgüzel et al. (2003 [triangle]); Mohd Lair et al. (2009a [triangle],b [triangle]); Li et al. (2009 [triangle]); Zhang et al. (2009 [triangle]). For a similar hydrazone compound, see: Zhang (2009 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2200-scheme1.jpg

Experimental

Crystal data

  • C16H16N2O4
  • M r = 300.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2200-efi1.jpg
  • a = 17.692 (2) Å
  • b = 5.4131 (7) Å
  • c = 14.933 (2) Å
  • β = 97.431 (7)°
  • V = 1418.1 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.23 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.977, T max = 0.980
  • 8164 measured reflections
  • 3069 independent reflections
  • 2001 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.129
  • S = 1.03
  • 3069 reflections
  • 205 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032449/su2137sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032449/su2137Isup2.hkl

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

supplementary crystallographic information

Comment

Hydrazone compounds are readily synthesized by the reaction of aldehydes with hydrazides. A large number of hydrazone compounds have been reported (Alhadi et al., 2008; Küçükgüzel et al., 2003; Li et al., 2009; Zhang et al., 2009). Recently, the author reported on the crystal structure of a hydrazone compound derived from the reaction of 2-methoxybenzaldehyde with 4-methoxybenzohydrazide (Zhang, 2009). Herein, the crystal structure of the new title hydrazone, prepared from the reaction of 2-hydroxy-4-methoxybenzaldehyde with 4-methoxybenzohydrazide, is reported on.

The molecule structure of the title compound is illustrated in Fig. 1. The molecule adopts an E configuration about the C═N bond. The dihedral angle involving the two benzene rings is 8.7 (2)°. There is an intramolecular O1—H1···N1 hydrogen bond, involving the hydroxyl substituent and the hydrazide N-atom (Table 1). All the bond lengths are within normal values (Allen et al., 1987) and are comparable with those observed in similar compounds (Mohd Lair et al., 2009a,b; Zhang, 2009).

In the crystal structure of the title compound adjacent molecules are linked through intermolecular N—H···O hydrogen bonds, forming chains propagating in b direction (Table 1 and Fig. 2).

Experimental

2-Hydroxy-4-methoxybenzaldehyde (1.0 mmol, 152.2 mg) and 4-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were mixed in a methanol solution, and the mixture was refluxed for 1 h. Colorless block-shaped crystals of the title compound were formed by slow evaporation of the solution in air.

Refinement

Atom H2 attached to N2 was located from a difference electron-density map and freely refined with Uiso(H) restrained to 0.08 (2) Å2. The other H-atoms were included in calculated positions and refined as riding atoms: d(C—H) = 0.93–0.96 Å, d(O—H) = 0.82 Å, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl and O).

Figures

Fig. 1.
A view of the molecular structure of the title compound, showing 30% displacement ellipsoids. The intramolecular N-H···O hydrogen bond is shown as a dashed line.
Fig. 2.
A perspective view, along the c-axis, illustrating the infinite chain structure of the title compound. O-H···N and N-H···O hydrogen bonds are shown as dashed lines [see Table 1 for details; H atoms not involved ...

Crystal data

C16H16N2O4F(000) = 632
Mr = 300.31Dx = 1.407 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1647 reflections
a = 17.692 (2) Åθ = 2.3–24.5°
b = 5.4131 (7) ŵ = 0.10 mm1
c = 14.933 (2) ÅT = 298 K
β = 97.431 (7)°Block, colorless
V = 1418.1 (3) Å30.23 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3069 independent reflections
Radiation source: fine-focus sealed tube2001 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −21→22
Tmin = 0.977, Tmax = 0.980k = −6→6
8164 measured reflectionsl = −17→19

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0559P)2 + 0.2712P] where P = (Fo2 + 2Fc2)/3
3069 reflections(Δ/σ)max < 0.001
205 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = −0.16 e Å3

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
O10.25296 (7)0.8356 (2)0.42022 (10)0.0497 (4)
H10.20790.79860.40790.075*
O20.03919 (7)0.9056 (3)0.38193 (10)0.0550 (4)
O30.49908 (7)0.5665 (3)0.36425 (10)0.0584 (4)
O4−0.29179 (7)0.4958 (3)0.40281 (9)0.0479 (4)
N10.13948 (8)0.5576 (3)0.35985 (10)0.0426 (4)
N20.06360 (9)0.5020 (3)0.35871 (12)0.0449 (4)
C10.26537 (10)0.4485 (3)0.34327 (12)0.0375 (4)
C20.29666 (10)0.6628 (3)0.38635 (12)0.0381 (4)
C30.37456 (10)0.7056 (3)0.39548 (13)0.0419 (5)
H30.39490.84540.42580.050*
C40.42197 (10)0.5403 (4)0.35937 (13)0.0425 (5)
C50.39204 (11)0.3296 (4)0.31433 (13)0.0464 (5)
H50.42370.22020.28890.056*
C60.31544 (11)0.2860 (4)0.30805 (13)0.0437 (5)
H60.29590.14300.27930.052*
C70.18490 (10)0.3929 (4)0.33728 (12)0.0422 (5)
H70.16650.23890.31720.051*
C80.01619 (10)0.6911 (4)0.37443 (12)0.0407 (4)
C9−0.06413 (10)0.6228 (3)0.38074 (12)0.0375 (4)
C10−0.10700 (10)0.7816 (4)0.42781 (13)0.0429 (5)
H10−0.08430.92260.45480.052*
C11−0.18213 (11)0.7328 (4)0.43479 (13)0.0435 (5)
H11−0.21000.83990.46660.052*
C12−0.21659 (10)0.5231 (3)0.39429 (12)0.0374 (4)
C13−0.17495 (10)0.3632 (4)0.34784 (13)0.0437 (5)
H13−0.19790.22280.32060.052*
C14−0.09899 (10)0.4126 (4)0.34193 (13)0.0436 (5)
H14−0.07090.30300.31140.052*
C150.53412 (11)0.7685 (4)0.41459 (18)0.0660 (7)
H15A0.51540.92090.38730.099*
H15B0.58840.75990.41500.099*
H15C0.52220.76090.47540.099*
C16−0.32941 (11)0.2764 (4)0.36696 (15)0.0531 (5)
H16A−0.32560.26510.30350.080*
H16B−0.38210.28230.37590.080*
H16C−0.30570.13460.39740.080*
H20.0500 (13)0.341 (2)0.3594 (16)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0404 (8)0.0411 (8)0.0694 (9)0.0031 (6)0.0135 (7)−0.0102 (7)
O20.0463 (8)0.0446 (9)0.0753 (10)−0.0066 (7)0.0117 (7)−0.0086 (8)
O30.0352 (8)0.0575 (10)0.0830 (11)0.0003 (6)0.0101 (7)−0.0097 (8)
O40.0360 (7)0.0486 (8)0.0610 (9)0.0001 (6)0.0130 (6)−0.0039 (7)
N10.0330 (8)0.0451 (10)0.0502 (9)0.0006 (7)0.0069 (7)0.0031 (8)
N20.0322 (8)0.0430 (10)0.0598 (10)−0.0019 (7)0.0074 (7)0.0010 (9)
C10.0369 (10)0.0346 (10)0.0410 (10)0.0016 (8)0.0054 (8)0.0025 (8)
C20.0395 (10)0.0329 (10)0.0429 (10)0.0051 (8)0.0088 (8)0.0012 (8)
C30.0398 (10)0.0364 (11)0.0494 (11)−0.0002 (8)0.0048 (8)−0.0029 (9)
C40.0333 (10)0.0451 (12)0.0496 (11)0.0048 (8)0.0069 (8)0.0050 (9)
C50.0439 (11)0.0431 (12)0.0531 (12)0.0092 (9)0.0095 (9)−0.0035 (10)
C60.0442 (11)0.0358 (11)0.0508 (11)0.0026 (8)0.0052 (9)−0.0037 (9)
C70.0409 (11)0.0375 (11)0.0476 (11)−0.0024 (8)0.0030 (8)−0.0010 (9)
C80.0372 (10)0.0443 (12)0.0407 (10)−0.0016 (9)0.0051 (8)−0.0024 (9)
C90.0349 (9)0.0374 (10)0.0401 (10)0.0016 (8)0.0043 (8)0.0009 (8)
C100.0426 (11)0.0377 (11)0.0482 (11)0.0003 (8)0.0046 (9)−0.0071 (9)
C110.0453 (11)0.0403 (11)0.0459 (11)0.0075 (9)0.0093 (9)−0.0057 (9)
C120.0341 (9)0.0388 (11)0.0398 (10)0.0034 (8)0.0061 (7)0.0028 (8)
C130.0399 (11)0.0380 (11)0.0534 (12)−0.0016 (8)0.0064 (9)−0.0093 (9)
C140.0390 (10)0.0405 (11)0.0521 (11)0.0032 (8)0.0096 (9)−0.0096 (9)
C150.0375 (12)0.0611 (15)0.0982 (19)−0.0027 (10)0.0041 (11)−0.0059 (14)
C160.0390 (11)0.0527 (13)0.0678 (14)−0.0066 (9)0.0072 (10)−0.0012 (11)

Geometric parameters (Å, °)

O1—C21.353 (2)C6—H60.9300
O1—H10.8200C7—H70.9300
O2—C81.231 (2)C8—C91.483 (2)
O3—C41.364 (2)C9—C141.385 (3)
O3—C151.423 (3)C9—C101.395 (2)
O4—C121.361 (2)C10—C111.372 (2)
O4—C161.431 (2)C10—H100.9300
N1—C71.274 (2)C11—C121.389 (3)
N1—N21.374 (2)C11—H110.9300
N2—C81.363 (2)C12—C131.380 (2)
N2—H20.903 (10)C13—C141.384 (2)
C1—C61.398 (2)C13—H130.9300
C1—C21.405 (3)C14—H140.9300
C1—C71.447 (2)C15—H15A0.9600
C2—C31.387 (2)C15—H15B0.9600
C3—C41.383 (2)C15—H15C0.9600
C3—H30.9300C16—H16A0.9600
C4—C51.393 (3)C16—H16B0.9600
C5—C61.367 (3)C16—H16C0.9600
C5—H50.9300
C2—O1—H1109.5C14—C9—C10118.38 (17)
C4—O3—C15118.20 (15)C14—C9—C8123.83 (17)
C12—O4—C16117.91 (14)C10—C9—C8117.79 (17)
C7—N1—N2119.46 (17)C11—C10—C9120.98 (18)
C8—N2—N1117.10 (16)C11—C10—H10119.5
C8—N2—H2123.5 (15)C9—C10—H10119.5
N1—N2—H2118.2 (15)C10—C11—C12119.92 (17)
C6—C1—C2117.41 (16)C10—C11—H11120.0
C6—C1—C7120.80 (17)C12—C11—H11120.0
C2—C1—C7121.77 (16)O4—C12—C13124.80 (17)
O1—C2—C3117.15 (17)O4—C12—C11115.29 (16)
O1—C2—C1122.13 (16)C13—C12—C11119.90 (17)
C3—C2—C1120.71 (16)C12—C13—C14119.78 (18)
C4—C3—C2119.92 (18)C12—C13—H13120.1
C4—C3—H3120.0C14—C13—H13120.1
C2—C3—H3120.0C13—C14—C9121.03 (17)
O3—C4—C3124.39 (18)C13—C14—H14119.5
O3—C4—C5115.21 (16)C9—C14—H14119.5
C3—C4—C5120.40 (17)O3—C15—H15A109.5
C6—C5—C4119.08 (17)O3—C15—H15B109.5
C6—C5—H5120.5H15A—C15—H15B109.5
C4—C5—H5120.5O3—C15—H15C109.5
C5—C6—C1122.43 (18)H15A—C15—H15C109.5
C5—C6—H6118.8H15B—C15—H15C109.5
C1—C6—H6118.8O4—C16—H16A109.5
N1—C7—C1119.14 (18)O4—C16—H16B109.5
N1—C7—H7120.4H16A—C16—H16B109.5
C1—C7—H7120.4O4—C16—H16C109.5
O2—C8—N2121.38 (17)H16A—C16—H16C109.5
O2—C8—C9122.52 (17)H16B—C16—H16C109.5
N2—C8—C9116.10 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.862.577 (2)146
N2—H2···O2i0.90 (1)2.39 (1)3.281 (2)168 (2)

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2137).

References

  • Alhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584. [PMC free article] [PubMed]
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  • Küçükgüzel, S. G., Mazi, A., Sahin, F., Öztürk, S. & Stables, J. (2003). Eur. J. Med. Chem.38, 1005–1013. [PubMed]
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