PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1649.
Published online 2008 July 31. doi:  10.1107/S1600536808023891
PMCID: PMC2962188

N′-(2-Chloro­benzyl­idene)-3,4,5-tri­methoxy­benzohydrazide methanol solvate

Abstract

In the title compound, C17H17ClN2O4·CH4O, the dihedral angle between the benzene ring planes is 5.29 (6)°. Inter­molecular N—H(...)O and O—H(...)O hydrogen bonds link the mol­ecules into a chain along the a axis.

Related literature

For related literature, see: Allen et al. (1987 [triangle]), Bernardino et al. (2006 [triangle]); Ganjali et al. (2006 [triangle]); Gardner et al. (1991 [triangle]); Patole et al. (2003 [triangle])

An external file that holds a picture, illustration, etc.
Object name is e-64-o1649-scheme1.jpg

Experimental

Crystal data

  • C17H17ClN2O4·CH4O
  • M r = 380.82
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1649-efi1.jpg
  • a = 12.9356 (7) Å
  • b = 4.8718 (3) Å
  • c = 29.4119 (16) Å
  • V = 1853.53 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 173 (2) K
  • 0.48 × 0.40 × 0.39 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.895, T max = 0.913
  • 9008 measured reflections
  • 3916 independent reflections
  • 3561 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.080
  • S = 1.09
  • 3916 reflections
  • 240 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.17 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1846 Friedel pairs
  • Flack parameter: 0.04 (5)

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/S1600536808023891/hb2761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023891/hb2761Isup2.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 have attracted much attention due to their diverse range of bioactivities in pharmaceutical and agrochemical field (e.g. Bernardino et al., 2006; Ganjali et al., 2006). We now report the synthesis and structure of the title compound, (I), obtained by the condensation of 3,4,5-trimethoxybenzohydrazide with 2-chlorobenzaldehyde as a methanol solvate (Fig. 1).

The bond lengths and bond angles for (I) are within normal ranges (Allen et al., 1987). The two benzene rings are approximately planar, with a dihedral angle of 5.29 (6)°. The methanol molecules in the crystal are lined to the Schiff base moieties through intermolecular N—H···O and O—H···O hydrogen bonds to form a chain along the a axis, which helps to consolidate the packing (Fig 2).

Experimental

A mixture of 3,4,5-trimethoxybenzohydrazide (1 mmol) and 2-chlorobenzaldehyde in anhydrous ethanol (10 ml) was refluxed for 2 h. When the solution was cooled to room temperature, some white needles separated out. After filtration, colorless blocks of (I) were obtained by slow evaporation of a methanol solution.

Refinement

All H atoms were placed in geometrically idealized positions and allowed to ride on their parent atoms, with N—H = 0.88 Å, O—H = 0.84 Å, C—H = 0.95 (aromatic and N=CH), 0.98 (methyl) Å) and Uiso(H) = xUeq(C, N, O), where x = 1.5 for the methyl and hydroxyl groups, x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 50% probability level.
Fig. 2.
The packing of (I), viewed down the b axis. The dashed lines represent the hydrogen bonding interactions.

Crystal data

C17H17ClN2O4·CH4OF000 = 800
Mr = 380.82Dx = 1.365 Mg m3
Orthorhombic, Pna21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 5318 reflections
a = 12.9356 (7) Åθ = 2.6–27.0º
b = 4.8718 (3) ŵ = 0.24 mm1
c = 29.4119 (16) ÅT = 173 (2) K
V = 1853.53 (18) Å3Block, colorless
Z = 40.48 × 0.40 × 0.39 mm

Data collection

Bruker SMART 1000 CCD diffractometer3916 independent reflections
Radiation source: fine-focus sealed tube3561 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 173(2) Kθmax = 27.0º
ω scansθmin = 2.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −16→8
Tmin = 0.895, Tmax = 0.913k = −5→6
9008 measured reflectionsl = −37→36

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031  w = 1/[σ2(Fo2) + (0.039P)2 + 0.3064P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080(Δ/σ)max = 0.012
S = 1.09Δρmax = 0.20 e Å3
3916 reflectionsΔρmin = −0.17 e Å3
240 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 1846 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (5)
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 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
Cl10.88399 (4)−0.29291 (12)0.98890 (2)0.04522 (15)
C10.93423 (13)0.2105 (4)0.75620 (6)0.0215 (3)
C20.85309 (13)0.0229 (4)0.75340 (6)0.0211 (3)
H20.8352−0.08660.77890.025*
C30.79858 (12)−0.0025 (3)0.71285 (6)0.0213 (3)
C40.82468 (13)0.1595 (3)0.67522 (6)0.0209 (3)
C50.90935 (13)0.3386 (4)0.67796 (6)0.0221 (3)
C60.96347 (13)0.3656 (4)0.71860 (6)0.0216 (3)
H61.02010.48920.72070.026*
C70.99585 (13)0.2484 (4)0.79886 (6)0.0231 (4)
C80.96354 (14)0.0864 (4)0.91319 (7)0.0308 (4)
H80.89490.01740.91210.037*
C91.02227 (15)0.0827 (4)0.95597 (6)0.0286 (4)
C100.99287 (15)−0.0824 (4)0.99280 (7)0.0319 (4)
C111.04956 (19)−0.0869 (5)1.03275 (7)0.0403 (5)
H111.0289−0.20291.05710.048*
C121.13525 (18)0.0753 (5)1.03723 (7)0.0435 (5)
H121.17310.07531.06490.052*
C131.16701 (18)0.2405 (5)1.00118 (7)0.0416 (5)
H131.22700.35171.00410.050*
C141.11093 (16)0.2419 (5)0.96120 (7)0.0362 (5)
H141.13340.35410.93670.043*
C150.69115 (15)−0.3585 (4)0.74240 (6)0.0260 (4)
H15A0.7517−0.46610.75150.039*
H15B0.6361−0.48270.73240.039*
H15C0.6668−0.24970.76830.039*
C160.71561 (18)0.3559 (4)0.61922 (7)0.0386 (5)
H16A0.65810.39540.63990.058*
H16B0.68840.31750.58880.058*
H16C0.76190.51500.61790.058*
C171.01472 (14)0.6703 (4)0.63995 (7)0.0302 (4)
H17A0.99890.81110.66270.045*
H17B1.02170.75650.61000.045*
H17C1.07960.57850.64800.045*
C181.2215 (2)0.7735 (5)0.86998 (9)0.0501 (6)
H18A1.19030.77800.90030.075*
H18B1.17390.85690.84800.075*
H18C1.28660.87630.87030.075*
N10.94896 (12)0.1728 (3)0.83814 (5)0.0268 (3)
H10.88410.11850.83850.032*
N21.00645 (11)0.1840 (3)0.87756 (5)0.0269 (3)
O10.71872 (9)−0.1791 (3)0.70587 (4)0.0259 (3)
O20.77131 (9)0.1235 (3)0.63530 (4)0.0259 (3)
O30.93290 (10)0.4729 (3)0.63872 (4)0.0308 (3)
O41.08391 (10)0.3399 (3)0.79778 (4)0.0298 (3)
O51.24118 (9)0.4964 (3)0.85732 (5)0.0328 (3)
H51.19000.43380.84310.049*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0469 (3)0.0485 (3)0.0403 (3)−0.0043 (2)0.0087 (2)0.0094 (3)
C10.0212 (8)0.0249 (9)0.0183 (8)0.0027 (7)−0.0023 (7)−0.0007 (7)
C20.0216 (8)0.0220 (8)0.0196 (8)0.0027 (6)0.0005 (7)0.0018 (7)
C30.0197 (8)0.0211 (8)0.0231 (8)0.0018 (6)0.0002 (7)−0.0038 (7)
C40.0212 (8)0.0242 (9)0.0171 (8)0.0044 (7)−0.0033 (6)−0.0027 (6)
C50.0219 (8)0.0239 (9)0.0205 (8)0.0015 (7)0.0007 (6)0.0009 (7)
C60.0205 (8)0.0243 (8)0.0201 (8)−0.0005 (7)−0.0017 (6)−0.0003 (7)
C70.0219 (8)0.0280 (9)0.0195 (8)0.0017 (7)−0.0028 (7)−0.0007 (7)
C80.0255 (9)0.0425 (11)0.0244 (9)−0.0010 (8)−0.0022 (7)0.0010 (8)
C90.0308 (10)0.0370 (10)0.0179 (8)0.0040 (8)−0.0003 (7)−0.0002 (8)
C100.0353 (10)0.0339 (10)0.0266 (9)0.0074 (8)0.0055 (8)−0.0001 (8)
C110.0580 (14)0.0406 (12)0.0221 (9)0.0135 (11)0.0047 (9)0.0069 (9)
C120.0540 (14)0.0538 (14)0.0227 (9)0.0139 (11)−0.0115 (9)−0.0045 (10)
C130.0419 (12)0.0519 (14)0.0309 (11)0.0028 (10)−0.0109 (9)−0.0042 (10)
C140.0397 (11)0.0458 (12)0.0233 (9)−0.0009 (10)−0.0031 (8)0.0043 (9)
C150.0269 (9)0.0232 (9)0.0278 (9)−0.0019 (7)0.0025 (7)−0.0004 (7)
C160.0433 (12)0.0374 (11)0.0351 (11)0.0081 (10)−0.0179 (9)−0.0010 (9)
C170.0269 (9)0.0345 (10)0.0293 (9)−0.0029 (8)−0.0006 (8)0.0078 (8)
C180.0638 (15)0.0453 (13)0.0412 (13)0.0120 (12)−0.0099 (12)−0.0078 (11)
N10.0206 (7)0.0415 (9)0.0184 (7)−0.0044 (6)−0.0041 (6)0.0019 (6)
N20.0257 (7)0.0370 (9)0.0180 (7)0.0010 (6)−0.0053 (6)0.0009 (6)
O10.0263 (6)0.0282 (7)0.0232 (6)−0.0049 (5)−0.0047 (5)0.0008 (5)
O20.0292 (6)0.0276 (6)0.0208 (6)0.0011 (5)−0.0064 (5)−0.0028 (5)
O30.0309 (6)0.0399 (7)0.0217 (6)−0.0096 (6)−0.0052 (6)0.0076 (6)
O40.0243 (6)0.0426 (8)0.0225 (7)−0.0089 (6)−0.0040 (5)0.0029 (6)
O50.0231 (6)0.0405 (7)0.0347 (7)0.0025 (6)−0.0042 (5)−0.0078 (6)

Geometric parameters (Å, °)

Cl1—C101.746 (2)C12—H120.9500
C1—C61.392 (2)C13—C141.382 (3)
C1—C21.394 (2)C13—H130.9500
C1—C71.498 (2)C14—H140.9500
C2—C31.391 (2)C15—O11.430 (2)
C2—H20.9500C15—H15A0.9800
C3—O11.360 (2)C15—H15B0.9800
C3—C41.401 (2)C15—H15C0.9800
C4—O21.373 (2)C16—O21.423 (2)
C4—C51.402 (2)C16—H16A0.9800
C5—O31.361 (2)C16—H16B0.9800
C5—C61.391 (2)C16—H16C0.9800
C6—H60.9500C17—O31.430 (2)
C7—O41.224 (2)C17—H17A0.9800
C7—N11.356 (2)C17—H17B0.9800
C8—N21.278 (2)C17—H17C0.9800
C8—C91.470 (2)C18—O51.423 (3)
C8—H80.9500C18—H18A0.9800
C9—C141.393 (3)C18—H18B0.9800
C9—C101.402 (3)C18—H18C0.9800
C10—C111.385 (3)N1—N21.378 (2)
C11—C121.368 (3)N1—H10.8800
C11—H110.9500O5—H50.8400
C12—C131.393 (3)
C6—C1—C2120.90 (15)C14—C13—H13120.1
C6—C1—C7117.00 (15)C12—C13—H13120.1
C2—C1—C7122.07 (14)C13—C14—C9121.6 (2)
C3—C2—C1119.38 (15)C13—C14—H14119.2
C3—C2—H2120.3C9—C14—H14119.2
C1—C2—H2120.3O1—C15—H15A109.5
O1—C3—C2124.80 (15)O1—C15—H15B109.5
O1—C3—C4114.85 (15)H15A—C15—H15B109.5
C2—C3—C4120.34 (15)O1—C15—H15C109.5
O2—C4—C3118.83 (15)H15A—C15—H15C109.5
O2—C4—C5121.43 (15)H15B—C15—H15C109.5
C3—C4—C5119.55 (14)O2—C16—H16A109.5
O3—C5—C6124.76 (15)O2—C16—H16B109.5
O3—C5—C4115.15 (14)H16A—C16—H16B109.5
C6—C5—C4120.09 (15)O2—C16—H16C109.5
C5—C6—C1119.63 (16)H16A—C16—H16C109.5
C5—C6—H6120.2H16B—C16—H16C109.5
C1—C6—H6120.2O3—C17—H17A109.5
O4—C7—N1122.52 (16)O3—C17—H17B109.5
O4—C7—C1121.23 (15)H17A—C17—H17B109.5
N1—C7—C1116.24 (15)O3—C17—H17C109.5
N2—C8—C9118.82 (17)H17A—C17—H17C109.5
N2—C8—H8120.6H17B—C17—H17C109.5
C9—C8—H8120.6O5—C18—H18A109.5
C14—C9—C10117.21 (17)O5—C18—H18B109.5
C14—C9—C8120.89 (18)H18A—C18—H18B109.5
C10—C9—C8121.89 (18)O5—C18—H18C109.5
C11—C10—C9121.40 (19)H18A—C18—H18C109.5
C11—C10—Cl1118.27 (16)H18B—C18—H18C109.5
C9—C10—Cl1120.33 (15)C7—N1—N2117.68 (14)
C12—C11—C10120.1 (2)C7—N1—H1121.2
C12—C11—H11119.9N2—N1—H1121.2
C10—C11—H11119.9C8—N2—N1116.16 (15)
C11—C12—C13119.97 (19)C3—O1—C15117.56 (13)
C11—C12—H12120.0C4—O2—C16115.90 (14)
C13—C12—H12120.0C5—O3—C17117.86 (14)
C14—C13—C12119.7 (2)C18—O5—H5109.5
C6—C1—C2—C3−2.2 (2)C14—C9—C10—C110.1 (3)
C7—C1—C2—C3179.86 (15)C8—C9—C10—C11179.16 (19)
C1—C2—C3—O1179.51 (15)C14—C9—C10—Cl1−178.94 (15)
C1—C2—C3—C4−0.2 (2)C8—C9—C10—Cl10.2 (3)
O1—C3—C4—O2−1.7 (2)C9—C10—C11—C121.1 (3)
C2—C3—C4—O2178.07 (15)Cl1—C10—C11—C12−179.86 (17)
O1—C3—C4—C5−176.74 (15)C10—C11—C12—C13−1.5 (3)
C2—C3—C4—C53.0 (2)C11—C12—C13—C140.7 (3)
O2—C4—C5—O30.7 (2)C12—C13—C14—C90.5 (3)
C3—C4—C5—O3175.62 (15)C10—C9—C14—C13−0.8 (3)
O2—C4—C5—C6−178.40 (16)C8—C9—C14—C13−180.0 (2)
C3—C4—C5—C6−3.5 (2)O4—C7—N1—N2−4.4 (3)
O3—C5—C6—C1−177.87 (16)C1—C7—N1—N2174.82 (16)
C4—C5—C6—C11.1 (3)C9—C8—N2—N1177.74 (17)
C2—C1—C6—C51.7 (3)C7—N1—N2—C8−173.39 (17)
C7—C1—C6—C5179.79 (15)C2—C3—O1—C15−2.3 (2)
C6—C1—C7—O4−21.9 (3)C4—C3—O1—C15177.43 (14)
C2—C1—C7—O4156.15 (17)C3—C4—O2—C16118.71 (19)
C6—C1—C7—N1158.87 (16)C5—C4—O2—C16−66.3 (2)
C2—C1—C7—N1−23.1 (2)C6—C5—O3—C17−4.5 (3)
N2—C8—C9—C1416.3 (3)C4—C5—O3—C17176.48 (15)
N2—C8—C9—C10−162.78 (19)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.882.012.8673 (19)165
O5—H5···O40.841.972.7904 (18)166

Symmetry codes: (i) x−1/2, −y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2761).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin. Trans. 2, pp. S1–19.
  • Bernardino, A. M. R., Gomes, A. O., Charret, K. S., Freita, A. C. C., Machado, G. M. C., Canto-Cavalheiro, M. M., Leon, L. L. & Amaral, V. F. (2006). Eur. J. Med. Chem.41, 80–87. [PubMed]
  • Bruker (2001). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2003). SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Ganjali, M. R., Faridbod, F., Norouzi, P. & Adib, M. (2006). Sens. Actuators B, 120, 119–124.
  • Gardner, T. S., Weins, R. & Lee, J. (1991). J. Org. Chem.26, 1514–1530.
  • Patole, J., Sandbhor, U., Padhye, S., Deobagkar, D. N., Anson, C. E. & Powell, A. (2003). Bioorg. Med. Chem. Lett.13, 51–55. [PubMed]
  • Sheldrick, G. M. (2003). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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