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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3240.
Published online 2010 November 20. doi:  10.1107/S160053681004701X
PMCID: PMC3011623

(E)-4-Meth­oxy-N′-(4-nitro­benzyl­idene)benzohydrazide methanol monosolvate

Abstract

The hydrazone mol­ecule of the title compound, C15H13N3O4·CH4O, is nearly planar, with a dihedral angle between the two benzene rings of 1.2 (4)°. The mol­ecule exists in a trans configuration with respect to the central methyl­idene unit. In the crystal, the benzohydrazide and methanol mol­ecules are linked through inter­molecular O—H(...)O, O—H(...)N and N—H(...)O hydrogen bonds, forming chains along the a axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 [triangle]); Raj et al. (2007 [triangle]); Jimenez-Pulido et al. (2008 [triangle]). For related structures, see: Ban & Li (2008a [triangle],b [triangle]); Li & Ban (2009a [triangle],b [triangle]); Yehye et al. (2008 [triangle]); Fun, Patil, Jebas et al., 2008 [triangle]; Fun, Patil, Rao et al., 2008 [triangle]; Yang et al. (2008 [triangle]); Ejsmont et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3240-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-66-o3240-efi1.jpg
  • a = 6.6482 (14) Å
  • b = 17.730 (3) Å
  • c = 13.898 (2) Å
  • β = 95.004 (3)°
  • V = 1631.9 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.20 × 0.17 × 0.17 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008 [triangle]) T min = 0.980, T max = 0.983
  • 12876 measured reflections
  • 3466 independent reflections
  • 1184 reflections with I > 2σ(I)
  • R int = 0.115

Refinement

  • R[F 2 > 2σ(F 2)] = 0.081
  • wR(F 2) = 0.204
  • S = 0.94
  • 3466 reflections
  • 222 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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/S160053681004701X/rz2522sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004701X/rz2522Isup2.hkl

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

Acknowledgments

The author acknowledges financial support by the Research Foundation of Liaoning Province (grant No. 2008470).

supplementary crystallographic information

Comment

Hydrazone compounds derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a large number of hydrazone compounds have been synthesized and structurally characterized (Yehye et al., 2008; Fun, Patil, Jebas et al., 2008; Fun, Patil, Rao et al., 2008; Yang et al., 2008; Ejsmont et al., 2008). Recently, we have reported a few such compounds (Ban & Li, 2008a,b; Li & Ban, 2009a,b). Herein the crystal structure of the title new compound is reported.

The asymmetric unit of the title compound consists of a hydrazone molecule and a methanol molecule (Fig. 1). The hydrazone molecule is nearly planar, the dihedral angle between the two benzene rings being 1.2 (4)°. The molecule exists in a trans configuration with respect to the central methylidene unit. In the crystal structure, the hydrazone molecules and the methanol molecules are linked through intermolecular O—H···O, O—H···N and N—H···O hydrogen bonds (Table 1), forming chains along the a axis (Fig. 2).

Experimental

The title compound was prepared by refluxing 4-nitrobenzaldehyde (1.0 mol) with 4-methoxybenzohydrazide (1.0 mol) in methanol (100 ml). Excess methanol was removed from the mixture by distillation. A colourless solid product was filtered, and washed three times with methanol. Colourless block-shaped crystals of the title compound were obtained from a methanol solution by slow evaporation in air.

Refinement

Atom H3A was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1)Å and Uiso fixed at 0.08 Å2. The remaining H atoms were placed in calculated positions (C—H = 0.93–0.96 Å and O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O and methyl C).

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
Fig. 2.
The packing diagram of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding are omitted for clarity.

Crystal data

C15H13N3O4·CH4OF(000) = 696
Mr = 331.33Dx = 1.349 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 794 reflections
a = 6.6482 (14) Åθ = 2.7–26.5°
b = 17.730 (3) ŵ = 0.10 mm1
c = 13.898 (2) ÅT = 298 K
β = 95.004 (3)°Block, colourless
V = 1631.9 (5) Å30.20 × 0.17 × 0.17 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3466 independent reflections
Radiation source: fine-focus sealed tube1184 reflections with I > 2σ(I)
graphiteRint = 0.115
ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)h = −8→8
Tmin = 0.980, Tmax = 0.983k = −22→22
12876 measured reflectionsl = −17→17

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)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204H atoms treated by a mixture of independent and constrained refinement
S = 0.94w = 1/[σ2(Fo2) + (0.0757P)2] where P = (Fo2 + 2Fc2)/3
3466 reflections(Δ/σ)max < 0.001
222 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = −0.27 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
N10.4536 (7)−0.3135 (2)0.1424 (3)0.0634 (12)
N20.1193 (5)0.0260 (2)0.1132 (2)0.0453 (9)
N30.0063 (5)0.0908 (2)0.1112 (3)0.0460 (9)
O10.3670 (6)−0.3698 (2)0.1665 (3)0.0923 (13)
O20.6283 (6)−0.3132 (2)0.1217 (3)0.0930 (13)
O30.2843 (4)0.15868 (16)0.0864 (2)0.0650 (10)
O4−0.3188 (4)0.43167 (16)0.0795 (2)0.0709 (10)
O50.5933 (4)0.05685 (17)0.1482 (3)0.0642 (10)
H50.48980.07670.12370.096*
C10.1378 (6)−0.1068 (2)0.1293 (3)0.0424 (11)
C20.3344 (6)−0.1112 (2)0.1018 (3)0.0529 (12)
H20.3964−0.06820.08010.063*
C30.4373 (6)−0.1786 (3)0.1064 (3)0.0549 (13)
H30.5680−0.18170.08760.066*
C40.3437 (7)−0.2407 (2)0.1391 (3)0.0493 (12)
C50.1521 (7)−0.2403 (3)0.1657 (3)0.0586 (13)
H5A0.0922−0.28400.18660.070*
C60.0480 (6)−0.1719 (3)0.1607 (3)0.0563 (13)
H6−0.0834−0.16990.17860.068*
C70.0276 (6)−0.0354 (3)0.1262 (3)0.0495 (12)
H7−0.1100−0.03500.13380.059*
C80.1041 (7)0.1569 (2)0.0971 (3)0.0461 (11)
C9−0.0195 (6)0.2263 (2)0.0959 (3)0.0449 (11)
C10−0.2157 (6)0.2311 (2)0.1201 (3)0.0508 (12)
H10−0.27850.18770.14030.061*
C11−0.3223 (6)0.2981 (2)0.1153 (3)0.0535 (12)
H11−0.45510.29980.13140.064*
C12−0.2287 (7)0.3619 (2)0.0864 (3)0.0540 (12)
C13−0.0345 (7)0.3593 (3)0.0605 (4)0.0829 (18)
H130.02770.40280.04020.100*
C140.0666 (7)0.2920 (3)0.0649 (4)0.0745 (16)
H140.19770.29040.04650.089*
C15−0.5263 (8)0.4384 (3)0.0967 (4)0.0833 (17)
H15A−0.60780.41150.04770.125*
H15B−0.56420.49070.09510.125*
H15C−0.54670.41770.15890.125*
C160.5721 (7)0.0414 (3)0.2467 (4)0.0823 (17)
H16A0.6181−0.00890.26170.123*
H16B0.43270.04590.25880.123*
H16C0.65120.07670.28630.123*
H3A−0.128 (2)0.087 (2)0.116 (3)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.077 (3)0.054 (3)0.060 (3)0.021 (3)0.006 (2)0.000 (2)
N20.041 (2)0.038 (2)0.056 (2)0.0098 (19)0.0024 (17)0.0028 (18)
N30.030 (2)0.039 (2)0.069 (3)0.0102 (19)0.0049 (19)0.0039 (19)
O10.117 (3)0.047 (2)0.115 (3)0.022 (2)0.025 (2)0.015 (2)
O20.078 (3)0.077 (3)0.128 (3)0.043 (2)0.031 (2)0.021 (2)
O30.0322 (17)0.053 (2)0.111 (3)0.0070 (15)0.0143 (17)0.0145 (18)
O40.056 (2)0.0407 (19)0.115 (3)0.0141 (17)−0.0002 (19)−0.0034 (19)
O50.0343 (18)0.056 (2)0.102 (3)0.0096 (16)0.0027 (17)0.017 (2)
C10.037 (3)0.040 (3)0.049 (3)0.002 (2)0.004 (2)0.001 (2)
C20.050 (3)0.036 (3)0.073 (3)0.004 (2)0.013 (2)0.000 (2)
C30.037 (3)0.050 (3)0.077 (4)0.005 (2)0.006 (2)0.002 (3)
C40.058 (3)0.042 (3)0.048 (3)0.017 (2)0.003 (2)0.003 (2)
C50.061 (3)0.044 (3)0.073 (3)−0.002 (3)0.017 (3)0.008 (2)
C60.048 (3)0.052 (3)0.070 (4)0.007 (3)0.017 (2)0.002 (3)
C70.034 (2)0.051 (3)0.063 (3)0.007 (2)0.004 (2)0.002 (2)
C80.042 (3)0.044 (3)0.053 (3)0.007 (2)0.001 (2)0.009 (2)
C90.035 (3)0.044 (3)0.056 (3)0.001 (2)−0.001 (2)0.002 (2)
C100.052 (3)0.031 (3)0.071 (3)0.003 (2)0.010 (2)0.007 (2)
C110.049 (3)0.039 (3)0.074 (3)0.008 (2)0.013 (2)0.009 (2)
C120.059 (3)0.034 (3)0.067 (3)0.013 (2)−0.005 (3)0.002 (2)
C130.051 (3)0.047 (3)0.152 (5)0.005 (3)0.020 (3)0.015 (3)
C140.037 (3)0.057 (3)0.131 (5)0.003 (3)0.012 (3)0.020 (3)
C150.091 (4)0.057 (3)0.106 (4)0.036 (3)0.029 (3)0.009 (3)
C160.069 (4)0.082 (4)0.094 (5)0.006 (3)−0.009 (3)−0.002 (3)

Geometric parameters (Å, °)

N1—O11.214 (4)C5—H5A0.9300
N1—O21.221 (5)C6—H60.9300
N1—C41.482 (5)C7—H70.9300
N2—C71.269 (5)C8—C91.479 (5)
N2—N31.372 (4)C9—C101.377 (5)
N3—C81.363 (5)C9—C141.383 (5)
N3—H3A0.902 (10)C10—C111.383 (5)
O3—C81.221 (4)C10—H100.9300
O4—C121.374 (5)C11—C121.367 (5)
O4—C151.426 (5)C11—H110.9300
O5—C161.415 (5)C12—C131.371 (6)
O5—H50.8200C13—C141.369 (6)
C1—C61.386 (5)C13—H130.9300
C1—C21.395 (5)C14—H140.9300
C1—C71.461 (5)C15—H15A0.9600
C2—C31.376 (5)C15—H15B0.9600
C2—H20.9300C15—H15C0.9600
C3—C41.362 (5)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.357 (5)C16—H16C0.9600
C5—C61.395 (5)
O1—N1—O2123.5 (4)N3—C8—C9116.5 (4)
O1—N1—C4118.7 (4)C10—C9—C14116.8 (4)
O2—N1—C4117.7 (5)C10—C9—C8125.8 (4)
C7—N2—N3116.9 (3)C14—C9—C8117.4 (4)
C8—N3—N2117.2 (3)C9—C10—C11122.2 (4)
C8—N3—H3A124 (3)C9—C10—H10118.9
N2—N3—H3A119 (3)C11—C10—H10118.9
C12—O4—C15119.1 (4)C12—C11—C10118.7 (4)
C16—O5—H5109.5C12—C11—H11120.7
C6—C1—C2118.6 (4)C10—C11—H11120.6
C6—C1—C7120.1 (4)C11—C12—C13120.9 (4)
C2—C1—C7121.3 (4)C11—C12—O4123.9 (4)
C3—C2—C1120.6 (4)C13—C12—O4115.2 (4)
C3—C2—H2119.7C14—C13—C12119.2 (5)
C1—C2—H2119.7C14—C13—H13120.4
C4—C3—C2118.5 (4)C12—C13—H13120.4
C4—C3—H3120.7C13—C14—C9122.2 (4)
C2—C3—H3120.7C13—C14—H14118.9
C5—C4—C3123.6 (4)C9—C14—H14118.9
C5—C4—N1118.0 (4)O4—C15—H15A109.5
C3—C4—N1118.4 (4)O4—C15—H15B109.5
C4—C5—C6117.7 (4)H15A—C15—H15B109.5
C4—C5—H5A121.2O4—C15—H15C109.5
C6—C5—H5A121.2H15A—C15—H15C109.5
C1—C6—C5120.9 (4)H15B—C15—H15C109.5
C1—C6—H6119.5O5—C16—H16A109.5
C5—C6—H6119.5O5—C16—H16B109.5
N2—C7—C1120.1 (4)H16A—C16—H16B109.5
N2—C7—H7120.0O5—C16—H16C109.5
C1—C7—H7120.0H16A—C16—H16C109.5
O3—C8—N3121.7 (4)H16B—C16—H16C109.5
O3—C8—C9121.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5···O30.822.032.812 (4)159
O5—H5···N20.822.613.194 (4)129
N3—H3A···O5i0.90 (1)2.02 (2)2.900 (4)166 (4)

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2522).

References

  • Ban, H.-Y. & Li, C.-M. (2008a). Acta Cryst. E64, o2177. [PMC free article] [PubMed]
  • Ban, H.-Y. & Li, C.-M. (2008b). Acta Cryst. E64, o2260. [PMC free article] [PubMed]
  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ejsmont, K., Zareef, M., Arfan, M., Bashir, S. A. & Zaleski, J. (2008). Acta Cryst. E64, o1128. [PMC free article] [PubMed]
  • Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. [PMC free article] [PubMed]
  • Fun, H.-K., Patil, P. S., Rao, J. N., Kalluraya, B. & Chantrapromma, S. (2008). Acta Cryst. E64, o1707. [PMC free article] [PubMed]
  • Jimenez-Pulido, S. B., Linares-Ordonez, F. M., Martinez-Martos, J. M., Moreno-Carretero, M. N., Quiros-Olozabal, M. & Ramirez-Exposito, M. J. (2008). J. Inorg. Biochem.102, 1677–1683. [PubMed]
  • Li, C.-M. & Ban, H.-Y. (2009a). Acta Cryst. E65, o876. [PMC free article] [PubMed]
  • Li, C.-M. & Ban, H.-Y. (2009b). Acta Cryst. E65, o883. [PMC free article] [PubMed]
  • Raj, K. K. V., Narayana, B., Ashalatha, B. V., Kumari, N. S. & Sarojini, B. K. (2007). Eur. J. Med. Chem.42, 425–429. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yang, T., Cao, G.-B., Xiang, J.-M. & Zhang, L.-H. (2008). Acta Cryst. E64, o1186. [PMC free article] [PubMed]
  • Yehye, W. A., Rahman, N. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o1824. [PMC free article] [PubMed]
  • Zhong, X., Wei, H.-L., Liu, W.-S., Wang, D.-Q. & Wang, X. (2007). Bioorg. Med. Chem. Lett.17, 3774–3777. [PubMed]

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