PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o2032.
Published online 2008 September 27. doi:  10.1107/S1600536808030894
PMCID: PMC2959387

4-Hydr­oxy-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)benzohydrazide mono­hydrate

Abstract

In the title compound, C15H14N2O4·H2O, the dihedral angle between the two aromatic rings is 33.3 (5)°. The meth­oxy group is twisted slightly away from the attached benzene ring [C—O—C—C = 13.8 (9)°]. An intra­molecular O—H(...)N hydrogen bond is observed. In the crystal structure, the mol­ecules are linked into a two-dimensional network parallel to the (010) plane by inter­molecular N—H(...)O, O—H(...)O and C—H(...)O hydrogen bonds

Related literature

For related structures, see: Lu et al. (2008a [triangle],b [triangle],c [triangle]); Nie (2008 [triangle]); He (2008 [triangle]); Shi et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2032-scheme1.jpg

Experimental

Crystal data

  • C15H14N2O4·H2O
  • M r = 304.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2032-efi1.jpg
  • a = 4.891 (2) Å
  • b = 12.171 (5) Å
  • c = 12.371 (5) Å
  • β = 95.724 (7)°
  • V = 732.8 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.08 × 0.07 × 0.07 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.992, T max = 0.993
  • 5972 measured reflections
  • 1582 independent reflections
  • 791 reflections with I > 2σ(I)
  • R int = 0.086

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.119
  • S = 0.92
  • 1582 reflections
  • 211 parameters
  • 6 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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/S1600536808030894/ci2678sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030894/ci2678Isup2.hkl

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

Acknowledgments

The author thanks the Scientific Research Foundation of Shaanxi University of Technology for financial support (project No. SLGQD0708).

supplementary crystallographic information

Comment

As part of our investigation of the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report here the crystal structure of the title new Schiff base compound.

The asymmetric unit of the title compound (Fig. 1), consists of a Schiff base molecule and a water molecule of crystallization. The bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings is 33.3 (5)°, indicating that the Schiff base molecule is twisted. An intramolecular O—H···N hydrogen bond is observed.

In the crystal structure, the molecules are linked into a two-dimensional network parallel to the (010) by intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds (Table 1).

Experimental

The title compound was prepared by the Schiff base condensation of 2-hydroxy-3-methoxybenzaldehyde (0.1 mol) and 4-hydroxybenzohydrazide (0.1 mmol) in 95% ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obatined by slow evaporation of a 95% ethanol solution at room temperature.

Refinement

The imino and water H atoms were located in a difference map and refined with N-H, O-H and H···H distances restrained to 0.90 (1), 0.85 (1), and 1.37 (2) Å, respectively. The other H atoms were positioned geometrically (C-H = 0.93-0.96 Å and O-H = 0.82 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl and O). A rotating group model was used for methyl and hydroxyl groups. In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates a hydrogen bond.
Fig. 2.
The crystal packing of the title compound, viewed along the c axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Crystal data

C15H14N2O4·H2OF(000) = 320
Mr = 304.30Dx = 1.379 Mg m3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yacCell parameters from 623 reflections
a = 4.891 (2) Åθ = 2.3–24.0°
b = 12.171 (5) ŵ = 0.11 mm1
c = 12.371 (5) ÅT = 298 K
β = 95.724 (7)°Block, colourless
V = 732.8 (5) Å30.08 × 0.07 × 0.07 mm
Z = 2

Data collection

Bruker APEXII CCD area-detector diffractometer1582 independent reflections
Radiation source: fine-focus sealed tube791 reflections with I > 2σ(I)
graphiteRint = 0.086
ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −6→6
Tmin = 0.992, Tmax = 0.993k = −15→15
5972 measured reflectionsl = −15→15

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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 0.92w = 1/[σ2(Fo2) + (0.0473P)2] where P = (Fo2 + 2Fc2)/3
1582 reflections(Δ/σ)max = 0.001
211 parametersΔρmax = 0.14 e Å3
6 restraintsΔρmin = −0.15 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
O10.2886 (8)0.7446 (3)0.9901 (3)0.0588 (11)
H10.21670.80480.97820.088*
O20.6029 (9)0.5752 (3)1.0195 (4)0.0747 (13)
O3−0.1590 (7)1.0380 (3)0.9939 (3)0.0564 (10)
O4−0.9973 (10)1.3626 (4)0.7359 (3)0.0823 (15)
H4−1.01971.36190.66940.123*
O50.3665 (9)1.0067 (4)0.0948 (3)0.0717 (13)
N10.1007 (8)0.9097 (3)0.8590 (3)0.0460 (11)
N2−0.0723 (9)0.9954 (4)0.8239 (3)0.0454 (11)
C10.4174 (11)0.7745 (4)0.8075 (5)0.0494 (14)
C20.4327 (11)0.7168 (4)0.9064 (5)0.0463 (14)
C30.6063 (12)0.6245 (5)0.9194 (5)0.0579 (17)
C40.7584 (13)0.5927 (5)0.8385 (6)0.072 (2)
H4A0.87320.53190.84840.087*
C50.7435 (13)0.6500 (6)0.7418 (6)0.073 (2)
H50.84840.62790.68700.088*
C60.5746 (12)0.7393 (5)0.7267 (5)0.0594 (16)
H60.56470.77710.66110.071*
C70.2392 (11)0.8680 (4)0.7868 (4)0.0485 (14)
H70.22430.89930.71800.058*
C8−0.2022 (10)1.0526 (4)0.8945 (5)0.0421 (13)
C9−0.4033 (10)1.1358 (4)0.8497 (4)0.0410 (13)
C10−0.5053 (12)1.2129 (5)0.9167 (5)0.0589 (16)
H10−0.43891.21380.98980.071*
C11−0.6996 (13)1.2877 (5)0.8800 (5)0.0694 (19)
H11−0.76501.33810.92770.083*
C12−0.7996 (11)1.2885 (5)0.7710 (5)0.0558 (16)
C13−0.7035 (13)1.2128 (5)0.7021 (5)0.0655 (18)
H13−0.76981.21250.62890.079*
C14−0.5079 (11)1.1370 (5)0.7412 (4)0.0549 (16)
H14−0.44501.08570.69380.066*
C150.8230 (15)0.4970 (7)1.0500 (8)0.107 (3)
H15A0.79830.43291.00480.160*
H15B0.81850.47631.12460.160*
H15C0.99700.53021.04050.160*
H2−0.076 (13)1.017 (5)0.7543 (17)0.080*
H5A0.211 (5)0.997 (5)0.058 (4)0.080*
H5B0.490 (7)0.992 (5)0.054 (4)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.063 (3)0.055 (2)0.057 (2)0.014 (2)0.001 (2)0.002 (2)
O20.071 (3)0.059 (2)0.090 (3)0.024 (2)−0.013 (3)0.007 (2)
O30.056 (3)0.081 (3)0.032 (2)0.017 (2)0.0050 (18)0.007 (2)
O40.090 (4)0.068 (3)0.086 (3)0.044 (3)−0.002 (3)−0.005 (2)
O50.054 (3)0.122 (4)0.038 (2)−0.011 (3)0.003 (2)0.005 (2)
N10.042 (3)0.043 (3)0.051 (3)0.004 (2)−0.004 (2)−0.003 (2)
N20.048 (3)0.050 (3)0.039 (3)0.009 (2)0.007 (2)0.002 (2)
C10.043 (3)0.046 (3)0.057 (4)0.004 (3)−0.004 (3)−0.022 (3)
C20.041 (4)0.046 (3)0.050 (3)0.001 (3)−0.001 (3)−0.014 (3)
C30.047 (4)0.047 (3)0.076 (5)0.010 (3)−0.012 (4)−0.010 (3)
C40.056 (5)0.063 (4)0.097 (6)0.025 (4)−0.001 (4)−0.027 (4)
C50.052 (4)0.076 (5)0.091 (6)0.011 (4)0.011 (4)−0.035 (4)
C60.048 (3)0.065 (4)0.064 (4)0.001 (3)0.000 (3)−0.017 (3)
C70.050 (4)0.055 (4)0.041 (3)0.003 (3)0.001 (3)−0.009 (3)
C80.034 (3)0.042 (3)0.051 (4)−0.001 (3)0.003 (3)−0.005 (3)
C90.041 (3)0.040 (3)0.042 (3)0.003 (3)0.002 (3)−0.002 (2)
C100.065 (4)0.068 (4)0.043 (3)0.009 (4)−0.001 (3)−0.007 (3)
C110.078 (5)0.070 (4)0.059 (5)0.037 (4)0.008 (4)−0.014 (3)
C120.052 (4)0.049 (3)0.064 (4)0.017 (3)−0.004 (3)−0.001 (3)
C130.076 (5)0.072 (4)0.047 (4)0.023 (4)−0.003 (3)0.004 (3)
C140.057 (4)0.063 (4)0.044 (3)0.025 (3)0.001 (3)−0.007 (3)
C150.066 (5)0.088 (5)0.160 (8)0.039 (4)−0.015 (5)0.028 (5)

Geometric parameters (Å, °)

O1—C21.352 (6)C4—H4A0.93
O1—H10.82C5—C61.367 (8)
O2—C31.377 (7)C5—H50.93
O2—C151.459 (7)C6—H60.93
O3—C81.240 (6)C7—H70.93
O4—C121.361 (6)C8—C91.480 (7)
O4—H40.82C9—C101.378 (7)
O5—H5A0.86 (3)C9—C141.388 (6)
O5—H5B0.84 (4)C10—C111.361 (7)
N1—C71.279 (6)C10—H100.93
N1—N21.385 (6)C11—C121.388 (8)
N2—C81.328 (6)C11—H110.93
N2—H20.90 (3)C12—C131.369 (7)
C1—C61.388 (7)C13—C141.381 (7)
C1—C21.407 (7)C13—H130.93
C1—C71.440 (7)C14—H140.93
C2—C31.407 (7)C15—H15A0.96
C3—C41.362 (8)C15—H15B0.96
C4—C51.379 (8)C15—H15C0.96
C2—O1—H1109.5C1—C7—H7118.5
C3—O2—C15116.3 (5)O3—C8—N2122.1 (5)
C12—O4—H4109.5O3—C8—C9120.7 (5)
H5A—O5—H5B108 (3)N2—C8—C9117.1 (5)
C7—N1—N2115.5 (4)C10—C9—C14117.0 (5)
C8—N2—N1120.4 (4)C10—C9—C8120.5 (5)
C8—N2—H2121 (4)C14—C9—C8122.5 (5)
N1—N2—H2118 (4)C11—C10—C9122.5 (5)
C6—C1—C2119.2 (5)C11—C10—H10118.8
C6—C1—C7119.0 (6)C9—C10—H10118.8
C2—C1—C7121.8 (5)C10—C11—C12119.7 (5)
O1—C2—C3117.8 (5)C10—C11—H11120.2
O1—C2—C1123.7 (5)C12—C11—H11120.2
C3—C2—C1118.5 (5)O4—C12—C13121.6 (5)
C4—C3—O2126.4 (6)O4—C12—C11119.0 (5)
C4—C3—C2120.7 (6)C13—C12—C11119.4 (5)
O2—C3—C2112.9 (5)C12—C13—C14120.0 (6)
C3—C4—C5120.5 (6)C12—C13—H13120.0
C3—C4—H4A119.7C14—C13—H13120.0
C5—C4—H4A119.7C13—C14—C9121.5 (5)
C6—C5—C4120.0 (6)C13—C14—H14119.3
C6—C5—H5120.0C9—C14—H14119.3
C4—C5—H5120.0O2—C15—H15A109.5
C5—C6—C1121.1 (6)O2—C15—H15B109.5
C5—C6—H6119.4H15A—C15—H15B109.5
C1—C6—H6119.4O2—C15—H15C109.5
N1—C7—C1122.9 (5)H15A—C15—H15C109.5
N1—C7—H7118.5H15B—C15—H15C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.992.687 (5)142
N2—H2···O5i0.90 (3)1.99 (3)2.820 (5)154 (5)
O4—H4···O2ii0.822.152.872 (7)147
O5—H5A···O3iii0.86 (3)1.97 (3)2.769 (6)156 (6)
O5—H5B···O3iv0.84 (4)2.01 (3)2.769 (6)148 (5)
C7—H7···O5i0.932.483.229 (7)138
C14—H14···O5i0.932.343.218 (7)158

Symmetry codes: (i) x−1/2, −y+2, z+1/2; (ii) x−3/2, −y+2, z−1/2; (iii) x, y, z−1; (iv) x+1, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2678).

References

  • 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.
  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • He, L. (2008). Acta Cryst. E64, o82. [PMC free article] [PubMed]
  • Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008a). Acta Cryst. E64, o1693. [PMC free article] [PubMed]
  • Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694. [PMC free article] [PubMed]
  • Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008c). Acta Cryst. E64, o1695. [PMC free article] [PubMed]
  • Nie, Y. (2008). Acta Cryst. E64, o471. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shi, X.-F., Liu, C.-Y., Liu, B. & Yuan, C.-C. (2007). Acta Cryst. E63, o1295–o1296.

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