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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1609.
Published online 2009 June 17. doi:  10.1107/S1600536809022624
PMCID: PMC2969251

N′-(2,4-Dichloro­benzyl­idene)-4-methoxy­benzohydrazide methanol solvate

Abstract

In the title compound, C15H12Cl2N2O2·CH3OH, the hydrazone mol­ecule displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 4.6 (2)°. In the crystal structure, the hydrazone and methanol mol­ecules are linked into a chain propagating along the a axis via N—H(...)O and O—H(...)O hydrogen bonds.

Related literature

For the biological properties of hydrazone compounds, see: Küçükgüzel et al. (2003 [triangle]); Charkoudian et al. (2007 [triangle]). For the crystal structures of hydrazone compounds, see: Fun et al. (2008 [triangle]); Lo & Ng (2009 [triangle]); Ren (2009 [triangle]); Zhang (2009 [triangle]). For related structures, see: Wu (2009 [triangle]); Peng & Hou (2008 [triangle]); Mohd Lair et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1609-scheme1.jpg

Experimental

Crystal data

  • C15H12Cl2N2O2·CH4O
  • M r = 355.21
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1609-efi1.jpg
  • a = 6.7401 (11) Å
  • b = 8.9583 (14) Å
  • c = 14.567 (2) Å
  • α = 75.085 (2)°
  • β = 81.570 (2)°
  • γ = 83.445 (2)°
  • V = 838.1 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.40 mm−1
  • T = 298 K
  • 0.20 × 0.18 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.924, T max = 0.931
  • 4896 measured reflections
  • 3557 independent reflections
  • 2461 reflections with I > 2σ(I)
  • R int = 0.017

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.128
  • S = 1.03
  • 3557 reflections
  • 214 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [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 global, I. DOI: 10.1107/S1600536809022624/ci2826sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022624/ci2826Isup2.hkl

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

Acknowledgments

The authors acknowledge Qiqihar University for funding this study.

supplementary crystallographic information

Comment

Hydrazones possess excellent antibacterial, antifungal, and antitumor activities (Küçükgüzel et al., 2003; Charkoudian et al., 2007). Recently, the crystal structures of some hydrazone compounds have been reported (Fun et al., 2008; Lo & Ng, 2009; Ren, 2009; Zhang, 2009). We report herein the crystal structure of the title new hydrazone compound.

The asymmetric unit of the title compound contains a hydrazone molecule and a methanol molecule. In the hydrazone molecule, the dihedral angle between the two benzene rings is 4.6 (2)°. The hydrazone molecule exists in an E configuration with respect to the methylidene group. All the bond lengths are normal and comparable to those in similar hydrazone compounds (Wu, 2009; Peng & Hou, 2008; Mohd Lair et al., 2009).

In the crystal structure of the title compound, the hydrazone molecules are linked by the methanol molecules through N—H···O and O—H···O hydrogen bonds (Table 1), forming chains propagating along the a axis (Fig. 2).

Experimental

Equimolar quantities (1.0 mmol each) of 2,4-dichlorobenzaldehyde and 4-methoxybenzohydrazide were mixed and refluxed in methanol. The reaction mixture was cooled to room temperature to give a clear colourless solution. Colourless single crystals of the title compound were formed by slow evaporation of the solution in air.

Refinement

Atom H2 was located in a difference map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. Other H atoms were placed in calculated positions (C—H = 0.93–0.96 Å and O—H = 0.82 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O,Cmethyl).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids for the non-H atoms. H atoms are shown as spheres of arbitrary radius.
Fig. 2.
The packing diagram, viewed along the b axis. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

Crystal data

C15H12Cl2N2O2·CH4OZ = 2
Mr = 355.21F(000) = 368
Triclinic, P1Dx = 1.408 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7401 (11) ÅCell parameters from 1307 reflections
b = 8.9583 (14) Åθ = 2.3–26.7°
c = 14.567 (2) ŵ = 0.40 mm1
α = 75.085 (2)°T = 298 K
β = 81.570 (2)°Block, colourless
γ = 83.445 (2)°0.20 × 0.18 × 0.18 mm
V = 838.1 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer3557 independent reflections
Radiation source: fine-focus sealed tube2461 reflections with I > 2σ(I)
graphiteRint = 0.017
ω scansθmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −8→8
Tmin = 0.924, Tmax = 0.931k = −11→11
4896 measured reflectionsl = −18→16

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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.048P)2 + 0.3404P] where P = (Fo2 + 2Fc2)/3
3557 reflections(Δ/σ)max = 0.001
214 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = −0.31 e Å3

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
Cl10.24871 (10)0.73959 (10)1.31319 (5)0.0692 (2)
Cl20.81448 (12)0.99939 (9)1.42996 (5)0.0719 (3)
N10.6168 (3)0.8075 (2)1.04117 (13)0.0442 (5)
N20.5388 (3)0.7708 (2)0.96816 (13)0.0451 (5)
O10.8442 (2)0.7876 (2)0.88034 (12)0.0582 (5)
O20.4029 (3)0.5972 (2)0.58129 (13)0.0661 (5)
O30.1098 (3)0.7492 (2)0.01521 (13)0.0613 (5)
H30.01830.7737−0.01850.092*
C10.5714 (3)0.8617 (3)1.19309 (16)0.0415 (5)
C20.4710 (3)0.8331 (3)1.28613 (17)0.0451 (6)
C30.5433 (4)0.8734 (3)1.35947 (17)0.0502 (6)
H3A0.47480.85231.42100.060*
C40.7199 (4)0.9456 (3)1.33905 (17)0.0501 (6)
C50.8244 (4)0.9770 (3)1.24829 (17)0.0506 (6)
H50.94321.02621.23570.061*
C60.7498 (4)0.9343 (3)1.17690 (17)0.0469 (6)
H60.82050.95441.11580.056*
C70.4950 (4)0.8199 (3)1.11445 (16)0.0462 (6)
H70.36010.80291.11830.055*
C80.6669 (3)0.7618 (3)0.88846 (16)0.0416 (5)
C90.5841 (3)0.7173 (3)0.81095 (15)0.0411 (5)
C100.6995 (4)0.7383 (3)0.72207 (17)0.0490 (6)
H100.82260.78090.71300.059*
C110.6354 (4)0.6974 (3)0.64766 (17)0.0553 (7)
H110.71480.71290.58870.066*
C120.4530 (4)0.6333 (3)0.65966 (17)0.0487 (6)
C130.3364 (4)0.6112 (3)0.74703 (18)0.0557 (7)
H130.21350.56850.75590.067*
C140.4030 (4)0.6528 (3)0.82198 (17)0.0542 (7)
H140.32380.63700.88100.065*
C150.2166 (5)0.5339 (4)0.5880 (2)0.0752 (9)
H15A0.20990.44150.63910.113*
H15B0.20500.50920.52880.113*
H15C0.10840.60810.60080.113*
C160.0604 (5)0.6214 (3)0.0907 (2)0.0715 (8)
H16A0.17910.57530.11960.107*
H16B0.00610.54660.06660.107*
H16C−0.03770.65470.13760.107*
H20.4070 (17)0.761 (3)0.973 (2)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0488 (4)0.1016 (6)0.0583 (4)−0.0229 (4)0.0003 (3)−0.0181 (4)
Cl20.0865 (5)0.0888 (6)0.0534 (4)−0.0131 (4)−0.0237 (4)−0.0297 (4)
N10.0427 (11)0.0564 (12)0.0384 (10)−0.0082 (9)−0.0097 (8)−0.0159 (9)
N20.0362 (10)0.0655 (13)0.0396 (10)−0.0100 (10)−0.0066 (8)−0.0202 (9)
O10.0410 (10)0.0925 (14)0.0470 (10)−0.0223 (9)−0.0023 (7)−0.0221 (9)
O20.0677 (12)0.0936 (15)0.0495 (11)−0.0154 (11)−0.0066 (9)−0.0365 (10)
O30.0389 (10)0.0899 (14)0.0539 (11)−0.0146 (9)−0.0084 (8)−0.0097 (10)
C10.0419 (13)0.0438 (13)0.0402 (12)−0.0003 (10)−0.0089 (10)−0.0120 (10)
C20.0386 (12)0.0523 (15)0.0439 (13)−0.0012 (11)−0.0064 (10)−0.0114 (11)
C30.0509 (15)0.0626 (16)0.0381 (13)−0.0006 (12)−0.0054 (10)−0.0158 (11)
C40.0601 (16)0.0531 (15)0.0432 (13)0.0014 (12)−0.0188 (11)−0.0183 (11)
C50.0531 (15)0.0544 (15)0.0494 (14)−0.0124 (12)−0.0117 (11)−0.0152 (12)
C60.0495 (14)0.0539 (15)0.0386 (12)−0.0110 (11)−0.0029 (10)−0.0121 (11)
C70.0399 (13)0.0586 (15)0.0442 (13)−0.0076 (11)−0.0088 (10)−0.0164 (11)
C80.0399 (13)0.0474 (14)0.0384 (12)−0.0083 (10)−0.0066 (10)−0.0089 (10)
C90.0392 (12)0.0472 (13)0.0384 (12)−0.0056 (10)−0.0057 (9)−0.0116 (10)
C100.0406 (13)0.0641 (16)0.0443 (13)−0.0132 (11)−0.0016 (10)−0.0151 (12)
C110.0531 (15)0.0764 (19)0.0391 (13)−0.0106 (13)0.0034 (11)−0.0216 (13)
C120.0527 (15)0.0576 (15)0.0411 (13)−0.0039 (12)−0.0089 (11)−0.0198 (11)
C130.0486 (15)0.0778 (19)0.0495 (14)−0.0240 (13)−0.0027 (11)−0.0251 (13)
C140.0519 (15)0.0768 (18)0.0394 (13)−0.0224 (13)0.0029 (11)−0.0215 (12)
C150.071 (2)0.102 (2)0.0701 (19)−0.0163 (17)−0.0211 (16)−0.0415 (18)
C160.0693 (19)0.0626 (19)0.084 (2)−0.0067 (15)−0.0218 (16)−0.0125 (16)

Geometric parameters (Å, °)

Cl1—C21.745 (2)C6—H60.93
Cl2—C41.743 (2)C7—H70.93
N1—C71.268 (3)C8—C91.487 (3)
N1—N21.378 (2)C9—C141.380 (3)
N2—C81.356 (3)C9—C101.389 (3)
N2—H20.893 (10)C10—C111.369 (3)
O1—C81.226 (3)C10—H100.93
O2—C121.360 (3)C11—C121.385 (3)
O2—C151.417 (3)C11—H110.93
O3—C161.401 (3)C12—C131.374 (3)
O3—H30.82C13—C141.387 (3)
C1—C61.392 (3)C13—H130.93
C1—C21.397 (3)C14—H140.93
C1—C71.468 (3)C15—H15A0.96
C2—C31.378 (3)C15—H15B0.96
C3—C41.377 (4)C15—H15C0.96
C3—H3A0.93C16—H16A0.96
C4—C51.380 (3)C16—H16B0.96
C5—C61.373 (3)C16—H16C0.96
C5—H50.93
C7—N1—N2116.93 (19)C14—C9—C10117.8 (2)
C8—N2—N1117.23 (18)C14—C9—C8124.5 (2)
C8—N2—H2123.2 (19)C10—C9—C8117.7 (2)
N1—N2—H2119.4 (19)C11—C10—C9121.2 (2)
C12—O2—C15118.8 (2)C11—C10—H10119.4
C16—O3—H3109.5C9—C10—H10119.4
C6—C1—C2116.9 (2)C10—C11—C12120.4 (2)
C6—C1—C7120.4 (2)C10—C11—H11119.8
C2—C1—C7122.7 (2)C12—C11—H11119.8
C3—C2—C1122.3 (2)O2—C12—C13124.8 (2)
C3—C2—Cl1117.74 (19)O2—C12—C11115.8 (2)
C1—C2—Cl1119.93 (17)C13—C12—C11119.4 (2)
C4—C3—C2118.2 (2)C12—C13—C14119.7 (2)
C4—C3—H3A120.9C12—C13—H13120.2
C2—C3—H3A120.9C14—C13—H13120.2
C3—C4—C5121.8 (2)C9—C14—C13121.5 (2)
C3—C4—Cl2119.34 (19)C9—C14—H14119.2
C5—C4—Cl2118.9 (2)C13—C14—H14119.2
C6—C5—C4118.7 (2)O2—C15—H15A109.5
C6—C5—H5120.6O2—C15—H15B109.5
C4—C5—H5120.6H15A—C15—H15B109.5
C5—C6—C1122.1 (2)O2—C15—H15C109.5
C5—C6—H6119.0H15A—C15—H15C109.5
C1—C6—H6119.0H15B—C15—H15C109.5
N1—C7—C1118.6 (2)O3—C16—H16A109.5
N1—C7—H7120.7O3—C16—H16B109.5
C1—C7—H7120.7H16A—C16—H16B109.5
O1—C8—N2121.9 (2)O3—C16—H16C109.5
O1—C8—C9120.9 (2)H16A—C16—H16C109.5
N2—C8—C9117.20 (19)H16B—C16—H16C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.89 (1)2.01 (1)2.889 (3)167 (3)
O3—H3···O1ii0.821.992.780 (2)163

Symmetry codes: (i) x, y, z+1; (ii) x−1, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2826).

References

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