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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1084.
Published online 2010 April 14. doi:  10.1107/S1600536810012912
PMCID: PMC2979167

2-Hydr­oxy-N′-(2-hydr­oxy-3-meth­oxy-5-nitro­benzyl­idene)-3-methyl­benzo­hydrazide

Abstract

In the title compound, C16H15N3O6, the dihedral angle between the two benzene rings is 0.9 (2)°. The mol­ecule adopts an E configuration with respect to the C=N bond. There are intra­molecular O—H(...)N and O—H(...)O hydrogen bonds in the mol­ecule. In the crystal structure, mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds to form chains running along the c axis.

Related literature

For the biological properties of hydrazone compounds, see: Patil et al. (2010 [triangle]); Cukurovali et al. (2006 [triangle]). For the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 [triangle]); Lin & Sang (2009 [triangle]); Suleiman Gwaram et al. (2010 [triangle]). For the hydrazone compounds we reported recently, see: Han & Zhao (2010a [triangle],b [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For similar compounds, see: Li & Ban (2009 [triangle]); Lo & Ng (2009 [triangle]); Ning & Xu (2009 [triangle]); Zhu et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1084-scheme1.jpg

Experimental

Crystal data

  • C16H15N3O6
  • M r = 345.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1084-efi1.jpg
  • a = 7.482 (1) Å
  • b = 17.158 (1) Å
  • c = 12.250 (1) Å
  • β = 91.565 (1)°
  • V = 1572.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.10 × 0.07 × 0.05 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.989, T max = 0.994
  • 14545 measured reflections
  • 2612 independent reflections
  • 2165 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.108
  • S = 1.07
  • 2612 reflections
  • 233 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.14 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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/S1600536810012912/hg2671sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012912/hg2671Isup2.hkl

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

Acknowledgments

This work was supported by the Applied Chemistry Key Subject of Anhui Province (grant No. 200802187C).

supplementary crystallographic information

Comment

Hydrazone compounds have been widely investigated for their biological properties (Patil et al., 2010; Cukurovali et al., 2006). Furthermore, the crystal structures of the hydrazone compounds have also attracted much attention in recent years (Mohd Lair et al., 2009; Lin & Sang, 2009; Suleiman Gwaram et al., 2010). As a continuous work on the structural characterization of such compounds (Han & Zhao, 2010a,b), the title new hydrazone compound is reported.

In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 0.9 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There are intramolecular O—H···N and O—H···O hydrogen bonds in the molecule (Table 1). All the bond lengths are within normal ranges (Allen et al., 1987), and are comparable with those in the similar compounds (Li & Ban, 2009; Lo & Ng, 2009; Ning & Xu, 2009; Zhu et al., 2009).

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

Experimental

A mixture of 3-methoxy-5-nitrosalicylaldehyde (0.197 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 g, 1 mmol) in 50 ml methanol was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, single crystals of the title compound, suitable for X-ray diffraction, were formed.

Refinement

Amino H atom was located from a difference Fourier map and refined isotropically, with N—H distance restrained to 0.90 (1) Å. Other H atoms were positioned geometrically and refined using the riding-model approximation, with C—H = 0.93 or 0.96 Å, O—H = 0.82 Å, and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(methyl C and O).

Figures

Fig. 1.
The molecular structure of the title compound with atom labels and the 30% probability displacement ellipsoids for non-H atoms. Intramolecular hydrogen bonds are shown as dashed lines.
Fig. 2.
The molecular packing of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C16H15N3O6F(000) = 720
Mr = 345.31Dx = 1.459 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6384 reflections
a = 7.482 (1) Åθ = 2.4–28.1°
b = 17.158 (1) ŵ = 0.11 mm1
c = 12.250 (1) ÅT = 298 K
β = 91.565 (1)°Block, colourless
V = 1572.0 (3) Å30.10 × 0.07 × 0.05 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2612 independent reflections
Radiation source: fine-focus sealed tube2165 reflections with I > 2σ(I)
graphiteRint = 0.023
ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −8→8
Tmin = 0.989, Tmax = 0.994k = −20→19
14545 measured reflectionsl = −13→13

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.07w = 1/[σ2(Fo2) + (0.0597P)2 + 0.2485P] where P = (Fo2 + 2Fc2)/3
2612 reflections(Δ/σ)max = 0.001
233 parametersΔρmax = 0.14 e Å3
1 restraintΔρmin = −0.27 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 > 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
O10.91330 (15)0.99426 (5)0.21838 (9)0.0529 (3)
H10.86391.00750.16070.079*
O21.05158 (16)0.93423 (6)0.39521 (9)0.0569 (3)
O30.67111 (17)1.11702 (6)0.00680 (9)0.0596 (3)
O40.55183 (17)1.23435 (6)−0.09508 (10)0.0633 (3)
H40.59861.2096−0.04470.095*
O51.0371 (2)0.63937 (6)0.14205 (11)0.0805 (4)
O61.13335 (17)0.65067 (6)0.30689 (10)0.0654 (4)
N11.06881 (16)0.67848 (7)0.22311 (11)0.0481 (3)
N20.78019 (15)0.97366 (7)0.02075 (10)0.0428 (3)
N30.70013 (16)1.00078 (6)−0.07337 (10)0.0434 (3)
C10.91165 (17)0.87130 (8)0.12358 (11)0.0391 (3)
C20.94794 (18)0.91768 (8)0.21567 (12)0.0397 (3)
C31.02423 (19)0.88404 (8)0.31098 (12)0.0422 (3)
C41.06361 (18)0.80575 (8)0.31361 (12)0.0425 (4)
H4A1.11300.78300.37640.051*
C51.02806 (18)0.76137 (8)0.22055 (12)0.0406 (3)
C60.95409 (18)0.79211 (8)0.12723 (12)0.0423 (3)
H60.93210.76060.06650.051*
C71.1154 (3)0.90321 (10)0.49667 (14)0.0671 (5)
H7A1.03190.86540.52240.101*
H7B1.12810.94450.54910.101*
H7C1.22930.87880.48700.101*
C80.8290 (2)0.90257 (8)0.02500 (12)0.0444 (4)
H80.81130.8706−0.03570.053*
C90.64676 (18)1.07636 (8)−0.07544 (12)0.0398 (3)
C100.56400 (18)1.10707 (8)−0.17680 (12)0.0393 (3)
C110.52198 (18)1.18678 (8)−0.18113 (12)0.0433 (4)
C120.44698 (19)1.22062 (9)−0.27568 (13)0.0486 (4)
C130.4115 (2)1.17278 (10)−0.36333 (14)0.0566 (4)
H130.36041.1941−0.42660.068*
C140.4493 (2)1.09387 (10)−0.36069 (14)0.0587 (4)
H140.42301.0629−0.42140.070*
C150.5255 (2)1.06140 (9)−0.26864 (13)0.0493 (4)
H150.55191.0084−0.26730.059*
C160.4079 (2)1.30676 (10)−0.27722 (16)0.0659 (5)
H16A0.35631.3210−0.34700.099*
H16B0.51691.3352−0.26460.099*
H16C0.32551.3190−0.22100.099*
H30.686 (3)0.9691 (10)−0.1318 (12)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0724 (7)0.0306 (5)0.0552 (7)0.0048 (4)−0.0085 (5)−0.0008 (4)
O20.0815 (8)0.0413 (6)0.0468 (7)0.0050 (5)−0.0152 (5)−0.0065 (5)
O30.0876 (8)0.0438 (6)0.0464 (7)0.0091 (5)−0.0182 (6)−0.0042 (5)
O40.0868 (8)0.0393 (6)0.0628 (8)0.0129 (5)−0.0201 (6)−0.0052 (5)
O50.1370 (12)0.0401 (6)0.0630 (9)0.0209 (7)−0.0251 (8)−0.0099 (6)
O60.0919 (9)0.0429 (6)0.0603 (8)0.0125 (6)−0.0219 (6)0.0094 (5)
N10.0588 (8)0.0361 (6)0.0490 (9)0.0068 (5)−0.0062 (6)0.0023 (6)
N20.0485 (7)0.0384 (6)0.0413 (8)0.0007 (5)−0.0027 (5)0.0079 (5)
N30.0558 (7)0.0357 (6)0.0382 (8)0.0026 (5)−0.0060 (6)0.0050 (5)
C10.0416 (7)0.0353 (7)0.0401 (9)−0.0001 (5)−0.0008 (6)0.0039 (6)
C20.0417 (7)0.0320 (7)0.0455 (9)0.0005 (5)0.0009 (6)0.0020 (6)
C30.0455 (8)0.0390 (7)0.0417 (9)−0.0014 (6)−0.0026 (6)−0.0032 (6)
C40.0452 (8)0.0398 (7)0.0419 (9)0.0021 (6)−0.0059 (6)0.0043 (6)
C50.0443 (7)0.0320 (7)0.0453 (9)0.0034 (6)−0.0022 (6)0.0025 (6)
C60.0510 (8)0.0359 (7)0.0397 (9)0.0019 (6)−0.0029 (6)−0.0019 (6)
C70.0994 (14)0.0544 (10)0.0465 (11)0.0060 (9)−0.0192 (9)−0.0069 (8)
C80.0537 (9)0.0385 (7)0.0406 (9)0.0015 (6)−0.0034 (7)0.0017 (6)
C90.0436 (8)0.0359 (7)0.0396 (9)−0.0017 (6)−0.0019 (6)0.0019 (6)
C100.0418 (7)0.0381 (7)0.0381 (9)−0.0014 (6)0.0000 (6)0.0051 (6)
C110.0434 (7)0.0409 (7)0.0454 (9)0.0004 (6)−0.0010 (6)0.0033 (7)
C120.0448 (8)0.0495 (8)0.0514 (10)0.0019 (6)0.0005 (7)0.0149 (7)
C130.0556 (9)0.0691 (11)0.0449 (10)0.0022 (8)−0.0037 (7)0.0193 (8)
C140.0693 (11)0.0656 (11)0.0407 (10)−0.0021 (8)−0.0083 (8)−0.0010 (8)
C150.0588 (9)0.0442 (8)0.0447 (10)0.0004 (7)−0.0039 (7)0.0010 (7)
C160.0663 (11)0.0524 (10)0.0786 (13)0.0071 (8)−0.0083 (9)0.0239 (9)

Geometric parameters (Å, °)

O1—C21.3399 (16)C5—C61.363 (2)
O1—H10.8200C6—H60.9300
O2—C31.3553 (17)C7—H7A0.9600
O2—C71.423 (2)C7—H7B0.9600
O3—C91.2348 (17)C7—H7C0.9600
O4—C111.3469 (18)C8—H80.9300
O4—H40.8200C9—C101.470 (2)
O5—N11.2165 (16)C10—C151.395 (2)
O6—N11.2195 (16)C10—C111.4040 (19)
N1—C51.4547 (18)C11—C121.399 (2)
N2—C81.2739 (18)C12—C131.372 (2)
N2—N31.3664 (17)C12—C161.507 (2)
N3—C91.3569 (18)C13—C141.383 (2)
N3—H30.903 (9)C13—H130.9300
C1—C61.3958 (18)C14—C151.368 (2)
C1—C21.401 (2)C14—H140.9300
C1—C81.445 (2)C15—H150.9300
C2—C31.409 (2)C16—H16A0.9600
C3—C41.3754 (19)C16—H16B0.9600
C4—C51.391 (2)C16—H16C0.9600
C4—H4A0.9300
C2—O1—H1109.5H7A—C7—H7C109.5
C3—O2—C7117.87 (12)H7B—C7—H7C109.5
C11—O4—H4109.5N2—C8—C1120.36 (14)
O5—N1—O6122.35 (12)N2—C8—H8119.8
O5—N1—C5119.05 (12)C1—C8—H8119.8
O6—N1—C5118.60 (13)O3—C9—N3119.19 (13)
C8—N2—N3118.63 (13)O3—C9—C10122.42 (12)
C9—N3—N2117.60 (12)N3—C9—C10118.38 (13)
C9—N3—H3122.2 (13)C15—C10—C11118.41 (13)
N2—N3—H3120.2 (13)C15—C10—C9123.57 (12)
C6—C1—C2119.23 (13)C11—C10—C9118.02 (13)
C6—C1—C8118.69 (13)O4—C11—C12116.78 (13)
C2—C1—C8122.08 (12)O4—C11—C10121.90 (13)
O1—C2—C1122.93 (13)C12—C11—C10121.31 (14)
O1—C2—C3117.09 (13)C13—C12—C11117.67 (14)
C1—C2—C3119.98 (12)C13—C12—C16122.95 (15)
O2—C3—C4125.10 (14)C11—C12—C16119.39 (15)
O2—C3—C2114.82 (12)C12—C13—C14122.16 (15)
C4—C3—C2120.07 (13)C12—C13—H13118.9
C3—C4—C5118.66 (13)C14—C13—H13118.9
C3—C4—H4A120.7C15—C14—C13119.88 (16)
C5—C4—H4A120.7C15—C14—H14120.1
C6—C5—C4122.69 (12)C13—C14—H14120.1
C6—C5—N1118.46 (13)C14—C15—C10120.55 (14)
C4—C5—N1118.84 (13)C14—C15—H15119.7
C5—C6—C1119.37 (13)C10—C15—H15119.7
C5—C6—H6120.3C12—C16—H16A109.5
C1—C6—H6120.3C12—C16—H16B109.5
O2—C7—H7A109.5H16A—C16—H16B109.5
O2—C7—H7B109.5C12—C16—H16C109.5
H7A—C7—H7B109.5H16A—C16—H16C109.5
O2—C7—H7C109.5H16B—C16—H16C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O6i0.90 (1)2.22 (1)3.0190 (17)147 (2)
O4—H4···O30.821.792.5192 (15)148
O1—H1···N20.821.902.6166 (17)145

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2671).

References

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