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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2408.
Published online 2008 November 22. doi:  10.1107/S1600536808038464
PMCID: PMC2960056

(E)-N′-(5-Bromo-2-hydroxy­benzyl­idene)-3,4,5-trimethoxy­benzohydrazide

Abstract

The mol­ecule of the title compound, C17H17BrN2O5, assumes an E configuration, with the 5-bromo-2-hydroxy­phenyl and benzohydrazide units located on opposite sites of the C=N double bond. The dihedral angle between the planes of the two benzene rings is 32.48 (15)°. The crystal structure is stabilized by intra­molecular O—H(...)N and inter­molecular N—H(...)O hydrogen bonds.

Related literature

For related literature, see: Yang et al. (1996 [triangle]); Nawar & Hosny (2000 [triangle]); Pelagatti et al. (1999 [triangle]); Ainscough et al. (1998 [triangle]). For related structures, see: Diao & Yu (2006 [triangle]); Jing et al. (2005 [triangle]); Wang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2408-scheme1.jpg

Experimental

Crystal data

  • C17H17BrN2O5
  • M r = 409.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2408-efi1.jpg
  • a = 11.4157 (19) Å
  • b = 16.279 (3) Å
  • c = 9.3738 (16) Å
  • β = 100.210 (3)°
  • V = 1714.4 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.43 mm−1
  • T = 273 (2) K [Unusual. Please check]
  • 0.15 × 0.10 × 0.06 mm

Data collection

  • Bruker APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.712, T max = 0.868
  • 8954 measured reflections
  • 3037 independent reflections
  • 2065 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.097
  • S = 1.01
  • 3037 reflections
  • 228 parameters
  • H-atom parameters constrained
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.54 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [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 I, global. DOI: 10.1107/S1600536808038464/pv2120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038464/pv2120Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of China (grant No. 30571466).

supplementary crystallographic information

Comment

Salicyladelhyde hydrazones have received considerable attention because of their possible applications in catalysis and pharmacology (Yang et al., 1996; Nawar & Hosny, 2000; Pelagatti et al., 1999; Ainscough et al., 1998). As part of our ongoing investigation on acylhydrazone compounds (Wang et al., 2008) and their metal complexes, we have obtained the title compound, (I), from a condensation of 3,4,5-trimethoxybenzohydrazide and 5-bromo-2-hydroxybenzaldehyde, and report its crystal structure in this paper.

The molecular structure of (I) (Fig. 1) contains 3,4,5-trimethoxybenzohydrazide and 5-bromo-2-hydroxybenzaldehyde moities that are located on opposite sides of the C═N double bond exhibiting an E configuration about C═N. The dihedral angle between the mean-planes of the two benzene rings is 32.48 (15)°. The crystal structure involves an intramolecular hydrogen bond O1–H1···N2, and is further stabilized by an intermolecular hydrogen bonds N1–H1A···O2, resulting in chains of molecules extended along the c-axis; details are given in Table 1 and Fig. 2. The bond distances and bond angles in (I) are in agreement with the corresponding dimensions reported for some structures closely related to (I) (Diao & Yu, 2006; Jing et al., 2005; Wang et al., 2008). (

Experimental

An ethanol solution (50 ml) of 3,4,5-trimethoxybenzohydrazide (0.01 mol) and 5-bromo-2-hydroxybenzaldehyde (0.01 mol) was refluxed and stirred for 2h ; the mixture was cooled and the resulting solid product, (I), was collected by filtration. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in THF.

Refinement

All H atoms were placed geometrically at the distances: C—H(methyl) = 0.96, C—H(aryl) = 0.93, N—H = 0.86 and O—H = 0.82 Å and included in the refinement in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom.

Figures

Fig. 1.
A view of the molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
Fig. 2.
The packing of (I), showing the intermolecular hydrogen-bonded extended network.

Crystal data

C17H17BrN2O5F000 = 832
Mr = 409.24Dx = 1.586 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2452 reflections
a = 11.4157 (19) Åθ = 2.5–22.8º
b = 16.279 (3) ŵ = 2.43 mm1
c = 9.3738 (16) ÅT = 273 (2) K
β = 100.210 (3)ºBlock, colourless
V = 1714.4 (5) Å30.15 × 0.10 × 0.06 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer3037 independent reflections
Radiation source: fine-focus sealed tube2065 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 273(2) Kθmax = 25.1º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −13→12
Tmin = 0.712, Tmax = 0.868k = −19→19
8954 measured reflectionsl = −11→8

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037  w = 1/[σ2(Fo2) + (0.0439P)2 + 0.6769P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max = 0.002
S = 1.01Δρmax = 0.43 e Å3
3037 reflectionsΔρmin = −0.54 e Å3
228 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0171 (11)
Secondary atom site location: difference Fourier map

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
Br10.94048 (4)1.21831 (2)0.94475 (6)0.0865 (2)
O10.9086 (2)0.92631 (14)1.3259 (2)0.0609 (6)
H10.86770.88971.28240.091*
O20.74380 (19)0.70776 (12)1.2188 (2)0.0493 (5)
O30.6562 (2)0.42963 (12)0.9513 (2)0.0605 (6)
O40.4797 (2)0.47058 (14)0.7287 (2)0.0661 (7)
O50.42036 (19)0.62400 (14)0.6698 (2)0.0595 (6)
N10.7240 (2)0.78966 (13)1.0217 (2)0.0413 (6)
H1A0.69800.79440.93020.050*
N20.7787 (2)0.85483 (14)1.0984 (2)0.0392 (6)
C10.9120 (3)0.99080 (18)1.2363 (3)0.0446 (7)
C20.8549 (2)0.98993 (16)1.0913 (3)0.0400 (7)
C30.8637 (3)1.05886 (18)1.0069 (3)0.0485 (8)
H30.82521.05960.91070.058*
C40.9282 (3)1.12578 (18)1.0634 (4)0.0542 (8)
C50.9863 (3)1.1252 (2)1.2051 (4)0.0592 (9)
H51.03161.17021.24270.071*
C60.9772 (3)1.0587 (2)1.2899 (4)0.0573 (9)
H61.01581.05911.38610.069*
C70.7914 (2)0.91924 (17)1.0253 (3)0.0417 (7)
H70.75880.92060.92710.050*
C80.7105 (2)0.71797 (17)1.0892 (3)0.0369 (6)
C90.6508 (2)0.65335 (17)0.9912 (3)0.0381 (7)
C100.6826 (3)0.57283 (17)1.0217 (3)0.0416 (7)
H100.73970.56001.10230.050*
C110.6292 (3)0.51139 (17)0.9317 (3)0.0450 (7)
C120.5412 (3)0.52992 (18)0.8141 (3)0.0460 (7)
C130.5089 (3)0.61112 (19)0.7852 (3)0.0445 (7)
C140.5643 (2)0.67246 (18)0.8733 (3)0.0413 (7)
H140.54340.72700.85340.050*
C150.7519 (3)0.4079 (2)1.0611 (4)0.0713 (10)
H15A0.82330.43401.04310.107*
H15B0.76220.34931.06180.107*
H15C0.73550.42551.15330.107*
C160.5452 (4)0.4238 (2)0.6446 (4)0.0853 (12)
H16A0.57910.45950.58120.128*
H16B0.49350.38480.58800.128*
H16C0.60770.39520.70710.128*
C170.3907 (3)0.7059 (2)0.6315 (4)0.0697 (10)
H17A0.35380.73080.70520.105*
H17B0.33640.70700.54070.105*
H17C0.46160.73570.62250.105*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0686 (3)0.0506 (3)0.1438 (5)0.00267 (18)0.0284 (3)0.0265 (2)
O10.0746 (17)0.0646 (15)0.0377 (12)−0.0140 (12)−0.0059 (11)−0.0017 (11)
O20.0660 (14)0.0498 (12)0.0287 (11)0.0048 (10)−0.0008 (10)−0.0018 (9)
O30.0799 (16)0.0411 (12)0.0584 (14)−0.0084 (11)0.0066 (13)−0.0024 (11)
O40.0701 (16)0.0687 (15)0.0606 (15)−0.0312 (12)0.0147 (13)−0.0247 (12)
O50.0551 (14)0.0737 (16)0.0426 (13)−0.0110 (12)−0.0106 (11)−0.0072 (11)
N10.0504 (14)0.0429 (14)0.0266 (12)−0.0088 (11)−0.0039 (11)−0.0032 (11)
N20.0450 (14)0.0359 (13)0.0336 (13)−0.0029 (11)−0.0019 (11)−0.0071 (11)
C10.0470 (17)0.0485 (18)0.0377 (17)−0.0016 (14)0.0053 (15)−0.0063 (14)
C20.0383 (16)0.0407 (16)0.0394 (17)0.0028 (13)0.0032 (14)−0.0047 (13)
C30.0459 (18)0.0463 (18)0.0512 (19)0.0034 (14)0.0031 (15)0.0013 (15)
C40.0466 (19)0.0399 (17)0.079 (3)0.0017 (14)0.0184 (19)0.0001 (17)
C50.051 (2)0.0457 (19)0.082 (3)−0.0077 (15)0.0138 (19)−0.0220 (19)
C60.052 (2)0.063 (2)0.054 (2)−0.0096 (16)0.0002 (16)−0.0239 (18)
C70.0454 (17)0.0456 (17)0.0304 (15)−0.0010 (14)−0.0032 (13)−0.0056 (14)
C80.0372 (15)0.0422 (16)0.0308 (16)0.0025 (13)0.0051 (13)−0.0042 (13)
C90.0416 (16)0.0406 (16)0.0325 (15)−0.0050 (13)0.0077 (13)−0.0048 (13)
C100.0436 (17)0.0463 (17)0.0339 (16)−0.0040 (14)0.0043 (13)−0.0037 (13)
C110.0531 (19)0.0387 (16)0.0471 (18)−0.0075 (14)0.0194 (16)−0.0045 (14)
C120.0483 (18)0.0507 (18)0.0400 (18)−0.0182 (15)0.0107 (15)−0.0130 (15)
C130.0396 (17)0.060 (2)0.0333 (17)−0.0103 (14)0.0033 (14)−0.0069 (14)
C140.0429 (17)0.0436 (17)0.0371 (16)−0.0028 (13)0.0064 (14)−0.0015 (13)
C150.084 (3)0.0450 (19)0.083 (3)0.0038 (18)0.010 (2)0.0028 (18)
C160.113 (3)0.066 (2)0.075 (3)−0.008 (2)0.011 (3)−0.035 (2)
C170.056 (2)0.084 (3)0.061 (2)−0.0003 (19)−0.0123 (18)0.004 (2)

Geometric parameters (Å, °)

Br1—C41.892 (3)C5—H50.9300
O1—C11.350 (4)C6—H60.9300
O1—H10.8200C7—H70.9300
O2—C81.219 (3)C8—C91.481 (4)
O3—C111.371 (3)C9—C101.377 (4)
O3—C151.407 (4)C9—C141.381 (4)
O4—C121.366 (3)C10—C111.379 (4)
O4—C161.403 (4)C10—H100.9300
O5—C131.359 (3)C11—C121.386 (4)
O5—C171.406 (4)C12—C131.386 (4)
N1—C81.349 (3)C13—C141.376 (4)
N1—N21.369 (3)C14—H140.9300
N1—H1A0.8600C15—H15A0.9600
N2—C71.274 (3)C15—H15B0.9600
C1—C61.378 (4)C15—H15C0.9600
C1—C21.399 (4)C16—H16A0.9600
C2—C31.387 (4)C16—H16B0.9600
C2—C71.440 (4)C16—H16C0.9600
C3—C41.368 (4)C17—H17A0.9600
C3—H30.9300C17—H17B0.9600
C4—C51.375 (5)C17—H17C0.9600
C5—C61.357 (5)
C1—O1—H1109.5C14—C9—C8121.4 (3)
C11—O3—C15118.0 (2)C9—C10—C11119.4 (3)
C12—O4—C16116.3 (3)C9—C10—H10120.3
C13—O5—C17117.4 (2)C11—C10—H10120.3
C8—N1—N2120.2 (2)O3—C11—C10123.9 (3)
C8—N1—H1A119.9O3—C11—C12115.6 (3)
N2—N1—H1A119.9C10—C11—C12120.5 (3)
C7—N2—N1116.1 (2)O4—C12—C13117.9 (3)
O1—C1—C6118.1 (3)O4—C12—C11122.4 (3)
O1—C1—C2122.5 (3)C13—C12—C11119.5 (3)
C6—C1—C2119.4 (3)O5—C13—C14124.3 (3)
C3—C2—C1118.5 (3)O5—C13—C12115.9 (3)
C3—C2—C7118.9 (3)C14—C13—C12119.8 (3)
C1—C2—C7122.5 (3)C13—C14—C9120.3 (3)
C4—C3—C2120.8 (3)C13—C14—H14119.9
C4—C3—H3119.6C9—C14—H14119.9
C2—C3—H3119.6O3—C15—H15A109.5
C3—C4—C5120.2 (3)O3—C15—H15B109.5
C3—C4—Br1119.8 (3)H15A—C15—H15B109.5
C5—C4—Br1120.0 (3)O3—C15—H15C109.5
C6—C5—C4119.9 (3)H15A—C15—H15C109.5
C6—C5—H5120.1H15B—C15—H15C109.5
C4—C5—H5120.1O4—C16—H16A109.5
C5—C6—C1121.2 (3)O4—C16—H16B109.5
C5—C6—H6119.4H16A—C16—H16B109.5
C1—C6—H6119.4O4—C16—H16C109.5
N2—C7—C2121.6 (3)H16A—C16—H16C109.5
N2—C7—H7119.2H16B—C16—H16C109.5
C2—C7—H7119.2O5—C17—H17A109.5
O2—C8—N1123.0 (2)O5—C17—H17B109.5
O2—C8—C9123.3 (3)H17A—C17—H17B109.5
N1—C8—C9113.7 (2)O5—C17—H17C109.5
C10—C9—C14120.4 (3)H17A—C17—H17C109.5
C10—C9—C8118.2 (3)H17B—C17—H17C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N20.821.922.642 (3)145
N1—H1A···O2i0.862.142.888 (3)146

Symmetry codes: (i) x, −y+3/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2120).

References

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  • Nawar, N. & Hosny, N. M. (2000). Transition Met. Chem.25, 1–8.
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