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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o668.
Published online 2008 March 5. doi:  10.1107/S1600536808005813
PMCID: PMC2960903

N′-(4-Methoxy­benzyl­idene)-4-nitro­benzo­hydrazide methanol solvate

Abstract

The title compound, C15H13N3O4·CH4O, was synthesized from the reaction of 4-methoxy­benzaldehyde with 4-nitro­benzohydrazide in methanol. The benzene rings of the Schiff base mol­ecule are nearly coplanar, making a dihedral angle of 7.0 (3)°. The methanol solvent mol­ecules are linked to the Schiff base mol­ecules by N—H(...)O, O—H(...)N and O—H(...)O hydrogen bonds, forming chains running parallel to the b axis.

Related literature

For related structures, see: Brückner et al. (2000 [triangle]); Diao (2007 [triangle]); Diao et al. (2007 [triangle], 2008 [triangle]); Harrop et al. (2003 [triangle]); Huang et al. (2007 [triangle]); Li et al. (2007 [triangle]); Ren et al. (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o668-scheme1.jpg

Experimental

Crystal data

  • C15H13N3O4·CH4O
  • M r = 331.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o668-efi1.jpg
  • a = 14.719 (3) Å
  • b = 6.631 (2) Å
  • c = 18.002 (3) Å
  • β = 113.17 (3)°
  • V = 1615.3 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.27 × 0.23 × 0.23 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.973, T max = 0.977
  • 9171 measured reflections
  • 3351 independent reflections
  • 1493 reflections with I > 2σ(I)
  • R int = 0.065

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.172
  • S = 0.95
  • 3351 reflections
  • 224 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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/S1600536808005813/rz2199sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005813/rz2199Isup2.hkl

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

Acknowledgments

This project is supported by a research grant from Dalian Medical University.

supplementary crystallographic information

Comment

Schiff base compounds have been found to have potential pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). Recently, a few Schiff base compounds derived from the reaction of aldehydes with benzohydrazides have been reported (Diao et al., 2008; Diao et al., 2007; Diao, 2007; Li et al., 2007; Huang et al., 2007). As a further study of such compounds, we report here the structure of the title compound.

The title compound (Fig. 1) consists of a Schiff base molecule and a lattice methanol molecule. The Schiff base molecule is nearly planar with the dihedral angle between the two phenyl rings of 7.0 (3)°. The dihedral angle between the C1—C6 phenyl ring and the O1/N1/O2 nitryl plane is 5.1 (3)°. The torsion angles C9—C8—N3—N2 and C4—C7—N2—N3 are 1.4 (3) and 1.6 (3)°, respectively. The methanol molecules are linked to the Schiff base molecules by N–H···O, O–H···N and O–H···O hydrogen bonds (Table 1) forming chains running parallel to the b axis.

Experimental

4-Methoxybenzaldehyde (0.1 mmol, 13.6 mg) and 4-nitrobenzohydrazide (0.1 mmol, 18.1 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 1 h and cooled to room temperature. After keeping the solution in air for five days, yellow block-like crystals were formed on slow evaporation of the solvent.

Refinement

H2A was located from a difference Fourier map and refined isotropically, with the N–H distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions and constrained to ride on their parent atoms, with C–H distances of 0.93–0.96 Å, O–H distance of 0.82 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and methyl C).

Figures

Fig. 1.
The structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

Crystal data

C15H13N3O4·CH4OF000 = 696
Mr = 331.33Dx = 1.362 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 670 reflections
a = 14.719 (3) Åθ = 2.4–24.5º
b = 6.631 (2) ŵ = 0.10 mm1
c = 18.002 (3) ÅT = 298 (2) K
β = 113.17 (3)ºBlock, yellow
V = 1615.3 (7) Å30.27 × 0.23 × 0.23 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3351 independent reflections
Radiation source: fine-focus sealed tube1493 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.065
T = 298(2) Kθmax = 26.5º
ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −18→18
Tmin = 0.973, Tmax = 0.977k = −8→7
9171 measured reflectionsl = −17→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.172  w = 1/[σ2(Fo2) + (0.07P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
3351 reflectionsΔρmax = 0.17 e Å3
224 parametersΔρmin = −0.17 e Å3
1 restraintExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0051 (12)

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
N10.3893 (2)0.1141 (5)0.43054 (18)0.0628 (8)
N20.37993 (17)0.4842 (3)0.09474 (14)0.0480 (6)
N30.38196 (16)0.5979 (3)0.03071 (14)0.0481 (6)
O10.35466 (19)−0.0546 (4)0.41861 (15)0.0913 (9)
O20.4269 (2)0.1901 (4)0.49761 (15)0.0915 (9)
O30.38954 (18)0.7649 (3)0.16870 (13)0.0712 (7)
O40.37929 (16)0.8238 (3)−0.31725 (12)0.0643 (6)
O50.34226 (17)0.0632 (3)0.04415 (13)0.0643 (6)
H50.3646−0.03900.07080.096*
C10.3883 (2)0.2315 (4)0.36036 (17)0.0474 (8)
C20.4211 (2)0.4269 (5)0.37219 (18)0.0587 (8)
H20.44420.48470.42340.070*
C30.4188 (2)0.5348 (5)0.30657 (18)0.0570 (8)
H30.44020.66800.31360.068*
C40.38535 (19)0.4503 (4)0.23005 (16)0.0433 (7)
C50.3527 (2)0.2511 (4)0.22030 (18)0.0500 (8)
H5A0.33030.19160.16950.060*
C60.3537 (2)0.1412 (4)0.28616 (18)0.0520 (8)
H60.33110.00880.27990.062*
C70.3851 (2)0.5799 (4)0.16214 (17)0.0484 (7)
C80.3756 (2)0.4971 (4)−0.03121 (18)0.0492 (7)
H80.36860.3578−0.03050.059*
C90.37877 (19)0.5910 (4)−0.10321 (16)0.0432 (7)
C100.3555 (2)0.4751 (5)−0.17273 (17)0.0525 (8)
H100.33930.3398−0.17170.063*
C110.3559 (2)0.5571 (4)−0.24324 (18)0.0535 (8)
H110.33890.4783−0.28950.064*
C120.3818 (2)0.7574 (4)−0.24426 (17)0.0475 (7)
C130.4075 (2)0.8738 (4)−0.17570 (17)0.0497 (8)
H130.42631.0075−0.17620.060*
C140.4054 (2)0.7901 (4)−0.10576 (17)0.0495 (8)
H140.42210.8695−0.05970.059*
C150.3969 (2)1.0303 (5)−0.3251 (2)0.0705 (10)
H15A0.34801.1096−0.31560.106*
H15B0.39331.0560−0.37870.106*
H15C0.46141.0657−0.28640.106*
C160.2426 (3)0.0315 (5)−0.0070 (2)0.0854 (11)
H16A0.20530.00160.02500.128*
H16B0.2380−0.0796−0.04250.128*
H16C0.21660.1508−0.03830.128*
H2A0.377 (2)0.3496 (16)0.0892 (19)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0707 (18)0.072 (2)0.0519 (19)0.0074 (16)0.0308 (16)0.0221 (16)
N20.0678 (16)0.0380 (13)0.0453 (15)−0.0013 (12)0.0298 (13)0.0086 (12)
N30.0634 (15)0.0436 (14)0.0426 (15)0.0012 (12)0.0266 (13)0.0089 (12)
O10.1079 (19)0.0897 (19)0.0742 (18)−0.0230 (16)0.0335 (15)0.0321 (15)
O20.137 (2)0.096 (2)0.0475 (16)0.0115 (16)0.0432 (16)0.0156 (15)
O30.128 (2)0.0367 (12)0.0565 (14)−0.0021 (12)0.0437 (14)0.0032 (10)
O40.0934 (16)0.0610 (14)0.0450 (13)−0.0019 (12)0.0342 (12)0.0065 (11)
O50.0883 (16)0.0432 (13)0.0554 (15)−0.0041 (12)0.0218 (13)0.0050 (10)
C10.0540 (18)0.0532 (19)0.0393 (18)0.0052 (15)0.0230 (15)0.0101 (15)
C20.081 (2)0.060 (2)0.0378 (18)−0.0057 (18)0.0263 (16)−0.0037 (15)
C30.080 (2)0.0474 (18)0.0464 (19)−0.0068 (16)0.0277 (17)0.0011 (15)
C40.0526 (17)0.0442 (17)0.0360 (17)0.0037 (14)0.0208 (14)0.0049 (13)
C50.0615 (19)0.0465 (18)0.0440 (18)−0.0040 (15)0.0229 (16)−0.0025 (14)
C60.0664 (19)0.0466 (18)0.050 (2)−0.0042 (15)0.0306 (16)0.0039 (15)
C70.0634 (19)0.0404 (18)0.0434 (18)−0.0016 (15)0.0231 (16)0.0035 (15)
C80.0605 (19)0.0452 (17)0.0458 (18)−0.0016 (15)0.0253 (16)0.0052 (15)
C90.0489 (16)0.0420 (16)0.0404 (17)−0.0004 (14)0.0194 (14)0.0058 (13)
C100.0657 (19)0.0420 (17)0.052 (2)−0.0042 (14)0.0247 (16)−0.0003 (15)
C110.072 (2)0.0487 (19)0.0405 (18)−0.0036 (16)0.0231 (16)−0.0042 (15)
C120.0551 (18)0.0543 (19)0.0362 (17)0.0042 (15)0.0214 (15)0.0052 (15)
C130.0638 (19)0.0410 (17)0.0476 (18)−0.0050 (14)0.0254 (16)0.0036 (14)
C140.0620 (19)0.0472 (19)0.0417 (18)−0.0036 (15)0.0231 (15)0.0004 (14)
C150.087 (2)0.066 (2)0.067 (2)−0.0062 (19)0.040 (2)0.0200 (18)
C160.092 (3)0.075 (3)0.087 (3)−0.002 (2)0.032 (2)0.000 (2)

Geometric parameters (Å, °)

N1—O11.213 (3)C5—H5A0.9300
N1—O21.222 (3)C6—H60.9300
N1—C11.479 (4)C8—C91.455 (4)
N2—C71.345 (3)C8—H80.9300
N2—N31.388 (3)C9—C141.383 (4)
N2—H2A0.897 (10)C9—C101.392 (4)
N3—C81.271 (3)C10—C111.383 (4)
O3—C71.232 (3)C10—H100.9300
O4—C121.372 (3)C11—C121.384 (4)
O4—C151.411 (3)C11—H110.9300
O5—C161.407 (4)C12—C131.376 (4)
O5—H50.8200C13—C141.388 (4)
C1—C61.366 (4)C13—H130.9300
C1—C21.370 (4)C14—H140.9300
C2—C31.370 (4)C15—H15A0.9600
C2—H20.9300C15—H15B0.9600
C3—C41.386 (4)C15—H15C0.9600
C3—H30.9300C16—H16A0.9600
C4—C51.392 (4)C16—H16B0.9600
C4—C71.493 (4)C16—H16C0.9600
C5—C61.387 (4)
O1—N1—O2123.4 (3)C9—C8—H8118.7
O1—N1—C1118.2 (3)C14—C9—C10118.0 (3)
O2—N1—C1118.4 (3)C14—C9—C8123.2 (3)
C7—N2—N3118.7 (2)C10—C9—C8118.8 (3)
C7—N2—H2A123 (2)C11—C10—C9121.3 (3)
N3—N2—H2A118 (2)C11—C10—H10119.3
C8—N3—N2115.1 (2)C9—C10—H10119.3
C12—O4—C15118.0 (2)C10—C11—C12119.3 (3)
C16—O5—H5109.5C10—C11—H11120.3
C6—C1—C2122.6 (3)C12—C11—H11120.3
C6—C1—N1118.6 (3)O4—C12—C13125.0 (3)
C2—C1—N1118.7 (3)O4—C12—C11114.6 (3)
C1—C2—C3118.2 (3)C13—C12—C11120.4 (3)
C1—C2—H2120.9C12—C13—C14119.5 (3)
C3—C2—H2120.9C12—C13—H13120.2
C2—C3—C4121.6 (3)C14—C13—H13120.2
C2—C3—H3119.2C9—C14—C13121.3 (3)
C4—C3—H3119.2C9—C14—H14119.3
C3—C4—C5118.6 (3)C13—C14—H14119.3
C3—C4—C7117.8 (3)O4—C15—H15A109.5
C5—C4—C7123.6 (3)O4—C15—H15B109.5
C6—C5—C4120.2 (3)H15A—C15—H15B109.5
C6—C5—H5A119.9O4—C15—H15C109.5
C4—C5—H5A119.9H15A—C15—H15C109.5
C1—C6—C5118.7 (3)H15B—C15—H15C109.5
C1—C6—H6120.7O5—C16—H16A109.5
C5—C6—H6120.7O5—C16—H16B109.5
O3—C7—N2122.6 (3)H16A—C16—H16B109.5
O3—C7—C4120.8 (3)O5—C16—H16C109.5
N2—C7—C4116.6 (2)H16A—C16—H16C109.5
N3—C8—C9122.6 (3)H16B—C16—H16C109.5
N3—C8—H8118.7

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O50.897 (10)2.049 (13)2.921 (3)164 (3)
O5—H5···N3i0.822.563.167 (3)133
O5—H5···O3i0.822.102.863 (3)154

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2199).

References

  • Brückner, C., Rettig, S. J. & Dolphin, D. (2000). Inorg. Chem.39, 6100–6106. [PubMed]
  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Diao, Y.-P. (2007). Acta Cryst. E63, m1453–m1454.
  • Diao, Y.-P., Shu, X.-H., Zhang, B.-J., Zhen, Y.-H. & Kang, T.-G. (2007). Acta Cryst. E63, m1816.
  • Diao, Y.-P., Zhen, Y.-H., Han, X. & Deng, S. (2008). Acta Cryst. E64, o101. [PMC free article] [PubMed]
  • Harrop, T. C., Olmstead, M. M. & Mascharak, P. K. (2003). Chem. Commun. pp. 410–411. [PubMed]
  • Huang, S.-S., Zhou, Q. & Diao, Y.-P. (2007). Acta Cryst. E63, o4659.
  • Li, K., Huang, S.-S., Zhang, B.-J., Meng, D.-L. & Diao, Y.-P. (2007). Acta Cryst. E63, m2291.
  • Ren, S., Wang, R., Komatsu, K., Bonaz-Krause, P., Zyrianov, Y., McKenna, C. E., Csipke, C., Tokes, Z. A. & Lien, E. J. (2002). J. Med. Chem.45, 410–419. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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