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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1648.
Published online 2008 July 31. doi:  10.1107/S1600536808023702
PMCID: PMC2962154

N′-(4-Fluoro­benzyl­idene)-3,4,5-trimethoxy­benzohydrazide

Abstract

The title compound, C17H17FN2O4, is of inter­est due to its potential pharmaceutical and agrochemical activity. All three meth­oxy groups are twisted with respect to the attached aromatic ring [C—C—O—C torsion angles = 10.43 (18), 97.38 (14), −19.34 (17)°] and the phenyl ring makes a dihedral angle of 40.6 (2)° with the plane through the remaining atoms in the mol­ecule. Inter­molecular N—H(...)O hydrogen bonds link the mol­ecules into chains running along the c axis.

Related literature

For related literature, see: Bernardino et al. (2006 [triangle]); Ganjali et al. (2006 [triangle]); Gardner et al. (1991 [triangle]); Lin et al. (2005 [triangle]); Patole et al. (2003 [triangle]); Liu et al. (2006 [triangle]); Zhou et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1648-scheme1.jpg

Experimental

Crystal data

  • C17H17FN2O4
  • M r = 332.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1648-efi1.jpg
  • a = 7.9194 (4) Å
  • b = 26.2496 (13) Å
  • c = 8.1271 (4) Å
  • β = 105.5470 (10)°
  • V = 1627.65 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 173 (2) K
  • 0.48 × 0.37 × 0.25 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.935, T max = 0.974
  • 9603 measured reflections
  • 3558 independent reflections
  • 2856 reflections with I > 2σ(I)
  • R int = 0.018

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.104
  • S = 1.07
  • 3558 reflections
  • 220 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2003 [triangle]); data reduction: SAINT-Plus; 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 I, New_Global_Publ_Block. DOI: 10.1107/S1600536808023702/fl2210sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023702/fl2210Isup2.hkl

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

Acknowledgments

The authors thank the Natural Science Youth Foundation of South China University of Technology for financial assistance (E5050570).

supplementary crystallographic information

Comment

Molecules involving Schiff bases are of interest due to their biological activity as pharmaceuticals and agrochemicals (Bernardino et al., 2006; Ganjali et al., 2006; Gardner et al., 1991; Patole et al., 2003;). In addition, Schiff base ligands have attracted much attention because they can readily form stable complexes with most metal ions (Lin et al., 2005; Zhou et al., 2005). We report herein the synthesis and crystal structure of the Schiff base compound (I), obtained by the condensation of 3,4,5-trimethoxybenzohydrazide and 4-fluorobenzaldehyde.

All three methoxy groups are twisted with respect their attached aromatic ring (10.41°, 97.38°, -19.34°, respectively) and the phenyl ring itself makes a dihedral angle of 40.64° with the plane through the remaining atoms (C7 through F1) in the molecule(Fig. 1). Similar geometry has been observed in a related hydrazone analogue (Liu et al., 2006). The bond lengths and bond angles are within normal ranges. Intermolecular N—H···O hydrogen bonds link the molecules into chains running along the c axis that help stabilize the molecular structure (Fig. 2).

Experimental

A mixture of 3,4,5-trimethoxybenzohydrazide (1 mmol) and 4-fluorobenzaldehyde (1 mmol) in anhydrous ethanol (10 ml) was refluxed at 80 °C for 2 h. When the solution was cooled to room temperature(25 °C), some white needles separated out. After filtration, colorless single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature.

Refinement

All H atoms were placed in geometrically idealized positions and refined as riding, with N—H = 0.88 Å, C—H = 0.95 (aromatic and N=CH), 0.98 (methyl) Å and Uiso(H) = xUeq(C, N), where x = 1.5 for the methyl, x = 1.2 for all other H atoms.

Figures

Fig. 1.
The Structure of the title compound, with the atom numbering. Displacement ellipsoids are the 50% probability level.
Fig. 2.
The packing of the title compound, viewed down the a axis. The dashed lines represent the hydrogen bonding interactions.

Crystal data

C17H17FN2O4F000 = 696
Mr = 332.33Dx = 1.356 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5449 reflections
a = 7.9194 (4) Åθ = 2.7–27.0º
b = 26.2496 (13) ŵ = 0.11 mm1
c = 8.1271 (4) ÅT = 173 (2) K
β = 105.5470 (10)ºBlock, colorless
V = 1627.65 (14) Å30.48 × 0.37 × 0.25 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer3558 independent reflections
Radiation source: fine-focus sealed tube2856 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.018
T = 173(2) Kθmax = 27.1º
ω scansθmin = 2.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −10→6
Tmin = 0.935, Tmax = 0.974k = −33→33
9603 measured reflectionsl = −10→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.104  w = 1/[σ2(Fo2) + (0.0561P)2 + 0.3099P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3558 reflectionsΔρmax = 0.27 e Å3
220 parametersΔρmin = −0.20 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
C10.63386 (15)0.68413 (4)0.23670 (15)0.0213 (3)
C20.65648 (16)0.63159 (5)0.23753 (15)0.0234 (3)
H20.72220.61480.33780.028*
C30.58205 (16)0.60404 (5)0.09044 (16)0.0242 (3)
C40.48089 (16)0.62887 (5)−0.05539 (15)0.0240 (3)
C50.44513 (15)0.68070 (5)−0.04828 (15)0.0233 (3)
C60.52479 (15)0.70882 (4)0.09643 (15)0.0222 (3)
H60.50510.74450.09970.027*
C70.73648 (15)0.71281 (4)0.39003 (15)0.0214 (2)
C80.94162 (16)0.83150 (5)0.43795 (16)0.0249 (3)
H80.92180.83790.31920.030*
C91.03374 (16)0.86967 (5)0.56060 (16)0.0249 (3)
C101.06439 (16)0.86332 (5)0.73717 (17)0.0274 (3)
H101.02870.83270.78040.033*
C111.14578 (19)0.90092 (5)0.84950 (18)0.0335 (3)
H111.16720.89650.96940.040*
C121.19497 (19)0.94501 (5)0.78240 (19)0.0365 (3)
C131.1702 (2)0.95280 (5)0.6106 (2)0.0373 (3)
H131.20760.98340.56900.045*
C141.08883 (19)0.91458 (5)0.49972 (18)0.0324 (3)
H141.07040.91910.38020.039*
C150.6792 (2)0.52504 (5)0.22518 (19)0.0372 (3)
H15A0.80230.53520.26880.056*
H15B0.67270.48850.19990.056*
H15C0.61660.53240.31140.056*
C160.5363 (2)0.59696 (6)−0.30234 (19)0.0423 (4)
H16A0.55610.6304−0.34740.063*
H16B0.49030.5734−0.39740.063*
H16C0.64720.5838−0.23000.063*
C170.25329 (17)0.74833 (5)−0.17173 (17)0.0300 (3)
H17A0.20880.7471−0.07030.045*
H17B0.15610.7551−0.27290.045*
H17C0.34060.7755−0.15840.045*
F11.27194 (14)0.98260 (3)0.89208 (12)0.0556 (3)
N10.79692 (13)0.75849 (4)0.35482 (12)0.0224 (2)
H10.77900.76840.24810.027*
N20.88701 (13)0.78964 (4)0.48641 (13)0.0225 (2)
O10.60103 (13)0.55283 (3)0.07321 (12)0.0323 (2)
O20.41211 (12)0.60182 (3)−0.20300 (11)0.0294 (2)
O30.33239 (12)0.70067 (3)−0.19160 (11)0.0308 (2)
O40.76599 (13)0.69488 (3)0.53497 (11)0.0292 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0232 (6)0.0219 (6)0.0196 (6)−0.0017 (5)0.0073 (5)−0.0015 (4)
C20.0266 (6)0.0214 (6)0.0214 (6)−0.0002 (5)0.0049 (5)0.0018 (5)
C30.0279 (6)0.0181 (6)0.0265 (6)−0.0025 (5)0.0071 (5)−0.0009 (5)
C40.0250 (6)0.0233 (6)0.0224 (6)−0.0051 (5)0.0040 (5)−0.0036 (5)
C50.0218 (6)0.0253 (6)0.0216 (6)−0.0008 (5)0.0038 (5)0.0020 (5)
C60.0243 (6)0.0188 (6)0.0236 (6)0.0000 (5)0.0067 (5)0.0000 (5)
C70.0248 (6)0.0208 (6)0.0186 (6)0.0033 (5)0.0059 (5)−0.0009 (4)
C80.0272 (6)0.0243 (6)0.0217 (6)0.0010 (5)0.0039 (5)−0.0024 (5)
C90.0222 (6)0.0220 (6)0.0289 (7)0.0012 (5)0.0040 (5)−0.0035 (5)
C100.0257 (6)0.0251 (6)0.0296 (7)−0.0002 (5)0.0044 (5)−0.0019 (5)
C110.0352 (7)0.0342 (7)0.0276 (7)−0.0028 (6)0.0026 (6)−0.0050 (6)
C120.0365 (8)0.0271 (7)0.0398 (8)−0.0053 (6)−0.0002 (6)−0.0114 (6)
C130.0407 (8)0.0254 (7)0.0429 (8)−0.0066 (6)0.0061 (6)0.0000 (6)
C140.0369 (7)0.0286 (7)0.0295 (7)−0.0027 (6)0.0054 (6)0.0002 (5)
C150.0513 (9)0.0191 (6)0.0347 (8)0.0005 (6)0.0004 (6)0.0027 (5)
C160.0440 (9)0.0516 (9)0.0317 (8)−0.0087 (7)0.0109 (7)−0.0147 (7)
C170.0272 (7)0.0311 (7)0.0302 (7)0.0052 (5)0.0049 (5)0.0054 (5)
F10.0731 (7)0.0357 (5)0.0470 (6)−0.0186 (5)−0.0030 (5)−0.0153 (4)
N10.0281 (5)0.0222 (5)0.0156 (5)−0.0024 (4)0.0034 (4)−0.0018 (4)
N20.0227 (5)0.0221 (5)0.0208 (5)0.0009 (4)0.0026 (4)−0.0048 (4)
O10.0456 (6)0.0178 (4)0.0289 (5)−0.0011 (4)0.0021 (4)−0.0013 (4)
O20.0314 (5)0.0283 (5)0.0252 (5)−0.0056 (4)0.0018 (4)−0.0067 (4)
O30.0347 (5)0.0280 (5)0.0235 (5)0.0041 (4)−0.0028 (4)0.0004 (4)
O40.0448 (6)0.0223 (4)0.0186 (4)−0.0007 (4)0.0055 (4)0.0006 (3)

Geometric parameters (Å, °)

C1—C21.3905 (17)C11—C121.379 (2)
C1—C61.3921 (17)C11—H110.9500
C1—C71.4957 (16)C12—F11.3596 (15)
C2—C31.3862 (17)C12—C131.372 (2)
C2—H20.9500C13—C141.3866 (19)
C3—O11.3639 (14)C13—H130.9500
C3—C41.4008 (17)C14—H140.9500
C4—O21.3748 (14)C15—O11.4252 (16)
C4—C51.3941 (17)C15—H15A0.9800
C5—O31.3679 (14)C15—H15B0.9800
C5—C61.3886 (16)C15—H15C0.9800
C6—H60.9500C16—O21.4354 (17)
C7—O41.2312 (14)C16—H16A0.9800
C7—N11.3499 (15)C16—H16B0.9800
C8—N21.2808 (16)C16—H16C0.9800
C8—C91.4629 (17)C17—O31.4276 (15)
C8—H80.9500C17—H17A0.9800
C9—C141.3931 (18)C17—H17B0.9800
C9—C101.3997 (18)C17—H17C0.9800
C10—C111.3812 (18)N1—N21.3829 (13)
C10—H100.9500N1—H10.8800
C2—C1—C6121.11 (11)F1—C12—C11118.32 (13)
C2—C1—C7117.04 (10)C13—C12—C11123.28 (13)
C6—C1—C7121.82 (10)C12—C13—C14117.94 (13)
C3—C2—C1119.26 (11)C12—C13—H13121.0
C3—C2—H2120.4C14—C13—H13121.0
C1—C2—H2120.4C13—C14—C9121.10 (13)
O1—C3—C2124.72 (11)C13—C14—H14119.5
O1—C3—C4115.18 (11)C9—C14—H14119.5
C2—C3—C4120.10 (11)O1—C15—H15A109.5
O2—C4—C5120.19 (11)O1—C15—H15B109.5
O2—C4—C3120.06 (11)H15A—C15—H15B109.5
C5—C4—C3119.70 (11)O1—C15—H15C109.5
O3—C5—C6124.21 (11)H15A—C15—H15C109.5
O3—C5—C4115.61 (10)H15B—C15—H15C109.5
C6—C5—C4120.17 (11)O2—C16—H16A109.5
C5—C6—C1119.17 (11)O2—C16—H16B109.5
C5—C6—H6120.4H16A—C16—H16B109.5
C1—C6—H6120.4O2—C16—H16C109.5
O4—C7—N1123.72 (11)H16A—C16—H16C109.5
O4—C7—C1121.75 (11)H16B—C16—H16C109.5
N1—C7—C1114.51 (10)O3—C17—H17A109.5
N2—C8—C9121.72 (11)O3—C17—H17B109.5
N2—C8—H8119.1H17A—C17—H17B109.5
C9—C8—H8119.1O3—C17—H17C109.5
C14—C9—C10118.70 (12)H17A—C17—H17C109.5
C14—C9—C8118.95 (12)H17B—C17—H17C109.5
C10—C9—C8122.33 (12)C7—N1—N2120.01 (9)
C11—C10—C9120.96 (13)C7—N1—H1120.0
C11—C10—H10119.5N2—N1—H1120.0
C9—C10—H10119.5C8—N2—N1114.60 (10)
C12—C11—C10118.01 (13)C3—O1—C15116.73 (10)
C12—C11—H11121.0C4—O2—C16111.45 (10)
C10—C11—H11121.0C5—O3—C17116.46 (10)
F1—C12—C13118.41 (13)
C6—C1—C2—C36.01 (18)N2—C8—C9—C10−1.37 (19)
C7—C1—C2—C3−171.90 (11)C14—C9—C10—C110.73 (19)
C1—C2—C3—O1177.13 (12)C8—C9—C10—C11−177.48 (12)
C1—C2—C3—C4−1.92 (18)C9—C10—C11—C120.4 (2)
O1—C3—C4—O2−1.36 (17)C10—C11—C12—F1178.69 (12)
C2—C3—C4—O2177.77 (11)C10—C11—C12—C13−1.3 (2)
O1—C3—C4—C5176.35 (11)F1—C12—C13—C14−178.91 (13)
C2—C3—C4—C5−4.53 (18)C11—C12—C13—C141.1 (2)
O2—C4—C5—O33.48 (17)C12—C13—C14—C90.1 (2)
C3—C4—C5—O3−174.22 (11)C10—C9—C14—C13−1.0 (2)
O2—C4—C5—C6−175.29 (11)C8—C9—C14—C13177.31 (12)
C3—C4—C5—C67.01 (18)O4—C7—N1—N2−4.82 (18)
O3—C5—C6—C1178.34 (11)C1—C7—N1—N2177.12 (9)
C4—C5—C6—C1−3.01 (17)C9—C8—N2—N1177.75 (10)
C2—C1—C6—C5−3.55 (17)C7—N1—N2—C8178.47 (11)
C7—C1—C6—C5174.26 (11)C2—C3—O1—C1510.43 (18)
C2—C1—C7—O4−35.84 (16)C4—C3—O1—C15−170.49 (12)
C6—C1—C7—O4146.27 (12)C5—C4—O2—C1697.38 (14)
C2—C1—C7—N1142.27 (11)C3—C4—O2—C16−84.92 (15)
C6—C1—C7—N1−35.63 (16)C6—C5—O3—C17−19.34 (17)
N2—C8—C9—C14−179.58 (12)C4—C5—O3—C17161.96 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.881.962.8238 (13)167

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: FL2210).

References

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