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ISSN: 2056-9890

(E)-N′-(4-Chloro­benzyl­­idene)-3,4,5-tri­meth­oxy­benzohydrazide

aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
*Correspondence e-mail: minwangyu@126.com

(Received 19 November 2008; accepted 21 November 2008; online 26 November 2008)

The title compound, C17H17ClN2O4, was synthesized from 3,4,5-trimethoxy­benzohydrazide and 4-chloro­benzaldehyde. In the crystal structure, packing is stabilized by intramolecular C—H⋯O and inter­molecular N—H⋯O and C—H⋯O hydrogen-bonding inter­actions.

Related literature

For related literature, see: Yang et al. (1996[Yang, Z. Y., Yang, R. D. & Yu, K. B. (1996). Polyhedron, 15, 3749-3753.]); Nawar et al. (2000[Nawar, N. & Hosny, N. M. (2000). Transition Met. Chem. 25, 1-8.]); Gardner et al. (1991[Gardner, T. S., Weins, R. & Lee, J. (1991). J. Org. Chem. 26, 1514-1530.]); Labouta et al. (1989[Labouta, I. M., Hassan, A. M., Aboulwafa, O. M. & Kader, O. (1989). Monatsh. Chem. 120, 571-574.]); Wang et al. (2008[Wang, Y.-M., Zhao, Z.-D., Chen, Y.-X. & Bi, L.-W. (2008). Acta Cryst. E64, o1009.]); Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H17ClN2O4

  • Mr = 348.78

  • Triclinic, [P \overline 1]

  • a = 5.119 (2) Å

  • b = 8.210 (4) Å

  • c = 20.276 (9) Å

  • α = 101.055 (7)°

  • β = 92.362 (7)°

  • γ = 101.459 (7)°

  • V = 816.9 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.26 mm−1

  • T = 273 (2) K

  • 0.12 × 0.10 × 0.06 mm

Data collection
  • Bruker APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.970, Tmax = 0.985

  • 4307 measured reflections

  • 2860 independent reflections

  • 2497 reflections with I > 2σ(I)

  • Rint = 0.017

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.128

  • S = 1.03

  • 2860 reflections

  • 218 parameters

  • H-atom parameters constrained

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O1i 0.86 2.18 2.943 (3) 147
C8—H8C⋯O4 0.96 2.26 2.896 (4) 123
C11—H11⋯O1i 0.93 2.43 3.145 (3) 134
C16—H16⋯O1ii 0.93 2.57 3.368 (3) 144
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

3,4,5-Trimethoxybenzohydrazide and their deviatives show moderate fungicidal and anti-bacterial activities (Gardner et al., 1991). The antibacterial activity of formylhydrazines and formylhydrazones has been reported by Labouta et al. (1989). Many derivatives of formylhydrazines have interesting biological properties. So we synthesized several derivatives of 3,4,5-trimethoxybenzohydrazide. In our previous paper we have reported the crystal structure of (E)—N'-(2-hydroxybenzylidene)-3,4,5-trimethoxybenzohydrazide (Wang et al., 2008). Now we synthesized the title compound (I) and report here its crystal structure.

The molecular structure of (I) is shown in Fig. 1. All bond lengths and angles in (I) are normal (Allen et al., 1987). In the crystal structure, there exist intramolecular C—H···O, and intermolecular N—H···O and C—H···O hydrogen bonding interactions (Table 1, Fig. 2).

Related literature top

For related literature, see: Yang et al. (1996); Nawar et al. (2000); Gardner et al. (1991); Labouta et al. (1989); Wang et al. (2008); Allen et al. (1987). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···. etc. Please revise this section as indicated.

Experimental top

An ethanol solution (50 ml) of 3,4,5-trimethoxybenzohydrazide (0.01 mol) and 4-chlorobenzaldehyde (0.01 mol) was refluxed and stirred for 2 h; 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 top

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

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title structure.
(E)-N'-(4-Chlorobenzylidene)-3,4,5-trimethoxybenzohydrazide top
Crystal data top
C17H17ClN2O4Z = 2
Mr = 348.78F(000) = 364
Triclinic, P1Dx = 1.418 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.119 (2) ÅCell parameters from 2557 reflections
b = 8.210 (4) Åθ = 2.6–28.3°
c = 20.276 (9) ŵ = 0.26 mm1
α = 101.055 (7)°T = 273 K
β = 92.362 (7)°Block, yellow
γ = 101.459 (7)°0.12 × 0.10 × 0.06 mm
V = 816.9 (7) Å3
Data collection top
Bruker APEX CCD area-detector
diffractometer
2860 independent reflections
Radiation source: fine-focus sealed tube2497 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ϕ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.970, Tmax = 0.985k = 99
4307 measured reflectionsl = 1824
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0602P)2 + 0.4783P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2860 reflectionsΔρmax = 0.59 e Å3
218 parametersΔρmin = 0.39 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.060 (5)
Crystal data top
C17H17ClN2O4γ = 101.459 (7)°
Mr = 348.78V = 816.9 (7) Å3
Triclinic, P1Z = 2
a = 5.119 (2) ÅMo Kα radiation
b = 8.210 (4) ŵ = 0.26 mm1
c = 20.276 (9) ÅT = 273 K
α = 101.055 (7)°0.12 × 0.10 × 0.06 mm
β = 92.362 (7)°
Data collection top
Bruker APEX CCD area-detector
diffractometer
2860 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2497 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.985Rint = 0.017
4307 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.03Δρmax = 0.59 e Å3
2860 reflectionsΔρmin = 0.39 e Å3
218 parameters
Special details top

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) top
xyzUiso*/Ueq
Cl10.98386 (15)0.10593 (8)0.26691 (3)0.0637 (2)
O10.5118 (3)0.4117 (2)0.66278 (7)0.0510 (4)
O20.5848 (4)0.5136 (2)0.92020 (8)0.0634 (5)
O30.9795 (4)0.7795 (3)0.95374 (9)0.0883 (7)
O41.3253 (4)0.8754 (2)0.86389 (9)0.0703 (6)
N10.8782 (3)0.3395 (2)0.57654 (8)0.0396 (4)
N20.9449 (3)0.4260 (2)0.64227 (8)0.0393 (4)
H21.10990.46300.65720.047*
C10.8360 (4)0.5329 (2)0.75470 (9)0.0365 (4)
C20.6692 (4)0.4815 (3)0.80214 (10)0.0408 (5)
H2A0.51690.39610.78880.049*
C30.7298 (4)0.5574 (3)0.86935 (10)0.0457 (5)
C40.9504 (5)0.6916 (3)0.88879 (11)0.0520 (6)
C51.1177 (4)0.7419 (3)0.84062 (11)0.0480 (5)
C61.0627 (4)0.6603 (3)0.77344 (10)0.0412 (5)
H61.17710.69090.74140.049*
C70.3631 (6)0.3744 (4)0.90386 (13)0.0673 (7)
H7A0.23450.39940.87360.101*
H7B0.28210.35490.94430.101*
H7C0.42250.27480.88270.101*
C81.2015 (8)0.7925 (6)0.99320 (16)0.1086 (14)
H8A1.20110.68601.00610.163*
H8B1.20730.87911.03280.163*
H8C1.35540.82200.96900.163*
C91.5185 (5)0.9198 (3)0.81913 (13)0.0563 (6)
H9A1.58260.82110.79900.084*
H9B1.66511.00470.84350.084*
H9C1.43920.96390.78450.084*
C100.7487 (4)0.4520 (2)0.68292 (10)0.0363 (4)
C111.0749 (4)0.3316 (3)0.54076 (10)0.0421 (5)
H111.24480.39150.55850.050*
C121.0395 (4)0.2302 (3)0.47225 (10)0.0378 (4)
C131.2396 (5)0.2560 (3)0.42946 (11)0.0527 (6)
H131.38980.34240.44380.063*
C141.2205 (5)0.1556 (3)0.36576 (11)0.0542 (6)
H141.35530.17490.33710.065*
C151.0009 (5)0.0277 (3)0.34555 (10)0.0433 (5)
C160.7968 (5)0.0006 (3)0.38638 (12)0.0540 (6)
H160.64710.08710.37170.065*
C170.8181 (4)0.1019 (3)0.44969 (11)0.0488 (5)
H170.68030.08410.47770.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0910 (5)0.0539 (4)0.0397 (3)0.0153 (3)0.0094 (3)0.0077 (3)
O10.0337 (8)0.0722 (11)0.0394 (8)0.0075 (7)0.0002 (6)0.0034 (7)
O20.0650 (11)0.0788 (12)0.0361 (9)0.0015 (9)0.0168 (7)0.0009 (8)
O30.0691 (12)0.1269 (19)0.0400 (10)0.0058 (12)0.0062 (9)0.0264 (11)
O40.0600 (11)0.0767 (12)0.0477 (10)0.0183 (9)0.0098 (8)0.0190 (8)
N10.0417 (9)0.0440 (9)0.0293 (8)0.0095 (7)0.0003 (7)0.0018 (7)
N20.0339 (8)0.0504 (10)0.0288 (8)0.0084 (7)0.0004 (6)0.0029 (7)
C10.0368 (10)0.0400 (10)0.0318 (10)0.0128 (8)0.0031 (8)0.0002 (8)
C20.0386 (11)0.0433 (11)0.0361 (11)0.0070 (9)0.0043 (8)0.0009 (9)
C30.0458 (12)0.0555 (13)0.0341 (11)0.0120 (10)0.0102 (9)0.0027 (9)
C40.0493 (12)0.0641 (15)0.0329 (11)0.0084 (11)0.0046 (9)0.0106 (10)
C50.0415 (11)0.0534 (13)0.0393 (11)0.0042 (10)0.0022 (9)0.0080 (10)
C60.0380 (11)0.0472 (12)0.0343 (10)0.0081 (9)0.0062 (8)0.0015 (9)
C70.0720 (17)0.0708 (17)0.0523 (15)0.0019 (14)0.0221 (13)0.0100 (13)
C80.092 (2)0.168 (4)0.0460 (17)0.008 (2)0.0029 (16)0.005 (2)
C90.0467 (13)0.0550 (14)0.0567 (14)0.0008 (10)0.0047 (11)0.0024 (11)
C100.0349 (10)0.0385 (10)0.0331 (10)0.0072 (8)0.0017 (8)0.0020 (8)
C110.0402 (11)0.0479 (12)0.0333 (10)0.0037 (9)0.0022 (8)0.0024 (9)
C120.0421 (11)0.0393 (10)0.0314 (10)0.0108 (8)0.0033 (8)0.0037 (8)
C130.0483 (13)0.0572 (14)0.0417 (12)0.0043 (10)0.0096 (10)0.0020 (10)
C140.0599 (14)0.0586 (14)0.0400 (12)0.0062 (11)0.0178 (10)0.0033 (10)
C150.0584 (13)0.0389 (11)0.0329 (10)0.0161 (9)0.0037 (9)0.0019 (8)
C160.0534 (13)0.0481 (13)0.0493 (13)0.0013 (10)0.0046 (10)0.0054 (10)
C170.0457 (12)0.0510 (13)0.0425 (12)0.0015 (10)0.0118 (9)0.0013 (10)
Geometric parameters (Å, º) top
Cl1—C151.742 (2)C7—H7A0.9600
O1—C101.223 (2)C7—H7B0.9600
O2—C31.357 (3)C7—H7C0.9600
O2—C71.419 (3)C8—H8A0.9600
O3—C81.337 (4)C8—H8B0.9600
O3—C41.362 (3)C8—H8C0.9600
O4—C51.361 (3)C9—H9A0.9600
O4—C91.411 (3)C9—H9B0.9600
N1—C111.270 (3)C9—H9C0.9600
N1—N21.379 (2)C11—C121.460 (3)
N2—C101.349 (3)C11—H110.9300
N2—H20.8600C12—C171.379 (3)
C1—C21.383 (3)C12—C131.380 (3)
C1—C61.383 (3)C13—C141.381 (3)
C1—C101.489 (3)C13—H130.9300
C2—C31.380 (3)C14—C151.365 (3)
C2—H2A0.9300C14—H140.9300
C3—C41.395 (3)C15—C161.371 (3)
C4—C51.393 (3)C16—C171.381 (3)
C5—C61.388 (3)C16—H160.9300
C6—H60.9300C17—H170.9300
C3—O2—C7117.98 (18)O3—C8—H8C109.5
C8—O3—C4120.7 (3)H8A—C8—H8C109.5
C5—O4—C9118.23 (18)H8B—C8—H8C109.5
C11—N1—N2114.90 (17)O4—C9—H9A109.5
C10—N2—N1119.35 (16)O4—C9—H9B109.5
C10—N2—H2120.3H9A—C9—H9B109.5
N1—N2—H2120.3O4—C9—H9C109.5
C2—C1—C6121.06 (18)H9A—C9—H9C109.5
C2—C1—C10116.43 (18)H9B—C9—H9C109.5
C6—C1—C10122.40 (18)O1—C10—N2122.65 (18)
C3—C2—C1119.68 (19)O1—C10—C1121.16 (17)
C3—C2—H2A120.2N2—C10—C1116.20 (17)
C1—C2—H2A120.2N1—C11—C12121.29 (19)
O2—C3—C2124.6 (2)N1—C11—H11119.4
O2—C3—C4115.37 (19)C12—C11—H11119.4
C2—C3—C4120.01 (19)C17—C12—C13118.34 (19)
O3—C4—C5122.0 (2)C17—C12—C11122.11 (18)
O3—C4—C3118.0 (2)C13—C12—C11119.44 (19)
C5—C4—C3119.73 (19)C12—C13—C14121.1 (2)
O4—C5—C6124.2 (2)C12—C13—H13119.4
O4—C5—C4115.72 (19)C14—C13—H13119.4
C6—C5—C4120.0 (2)C15—C14—C13119.0 (2)
C1—C6—C5119.33 (19)C15—C14—H14120.5
C1—C6—H6120.3C13—C14—H14120.5
C5—C6—H6120.3C14—C15—C16121.5 (2)
O2—C7—H7A109.5C14—C15—Cl1119.15 (17)
O2—C7—H7B109.5C16—C15—Cl1119.30 (17)
H7A—C7—H7B109.5C15—C16—C17118.7 (2)
O2—C7—H7C109.5C15—C16—H16120.7
H7A—C7—H7C109.5C17—C16—H16120.7
H7B—C7—H7C109.5C12—C17—C16121.3 (2)
O3—C8—H8A109.5C12—C17—H17119.3
O3—C8—H8B109.5C16—C17—H17119.3
H8A—C8—H8B109.5
C11—N1—N2—C10175.22 (19)O4—C5—C6—C1175.8 (2)
C6—C1—C2—C30.3 (3)C4—C5—C6—C12.2 (3)
C10—C1—C2—C3176.58 (19)N1—N2—C10—O15.0 (3)
C7—O2—C3—C23.4 (4)N1—N2—C10—C1174.86 (16)
C7—O2—C3—C4178.0 (2)C2—C1—C10—O133.9 (3)
C1—C2—C3—O2178.0 (2)C6—C1—C10—O1142.3 (2)
C1—C2—C3—C43.4 (3)C2—C1—C10—N2145.93 (19)
C8—O3—C4—C563.6 (4)C6—C1—C10—N237.9 (3)
C8—O3—C4—C3122.7 (3)N2—N1—C11—C12173.85 (18)
O2—C3—C4—O38.6 (3)N1—C11—C12—C1719.4 (3)
C2—C3—C4—O3170.1 (2)N1—C11—C12—C13164.4 (2)
O2—C3—C4—C5177.6 (2)C17—C12—C13—C140.4 (4)
C2—C3—C4—C53.7 (4)C11—C12—C13—C14176.0 (2)
C9—O4—C5—C69.0 (4)C12—C13—C14—C150.8 (4)
C9—O4—C5—C4172.9 (2)C13—C14—C15—C161.5 (4)
O3—C4—C5—O45.4 (4)C13—C14—C15—Cl1176.79 (19)
C3—C4—C5—O4179.0 (2)C14—C15—C16—C171.0 (4)
O3—C4—C5—C6172.7 (2)Cl1—C15—C16—C17177.36 (19)
C3—C4—C5—C60.9 (4)C13—C12—C17—C161.0 (3)
C2—C1—C6—C52.5 (3)C11—C12—C17—C16175.3 (2)
C10—C1—C6—C5173.5 (2)C15—C16—C17—C120.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.182.943 (3)147
C8—H8C···O40.962.262.896 (4)123
C11—H11···O1i0.932.433.145 (3)134
C16—H16···O1ii0.932.573.368 (3)144
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC17H17ClN2O4
Mr348.78
Crystal system, space groupTriclinic, P1
Temperature (K)273
a, b, c (Å)5.119 (2), 8.210 (4), 20.276 (9)
α, β, γ (°)101.055 (7), 92.362 (7), 101.459 (7)
V3)816.9 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.26
Crystal size (mm)0.12 × 0.10 × 0.06
Data collection
DiffractometerBruker APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.970, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
4307, 2860, 2497
Rint0.017
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.128, 1.03
No. of reflections2860
No. of parameters218
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.59, 0.39

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.862.182.943 (3)147
C8—H8C···O40.962.262.896 (4)123
C11—H11···O1i0.932.433.145 (3)134
C16—H16···O1ii0.932.573.368 (3)144
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1.
 

Acknowledgements

This work was supported by the Natural Science Fund of Jiangsu Province (No. BK2006011).

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