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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3063.
Published online 2010 November 6. doi:  10.1107/S1600536810043710
PMCID: PMC3011553

N′-(2,4-Dichloro­benzyl­idene)-2-methyl­benzohydrazide

Abstract

In the title hydrazone compound, C15H12Cl2N2O, the dihedral angle between the two benzene rings is 12.2 (2)°. In the crystal, mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds, forming forming C(4) chains propagating in [001].

Related literature

For general background to hydrazones, see: Rasras et al. (2010 [triangle]); Pyta et al. (2010 [triangle]); Angelusiu et al. (2010 [triangle]). For the crystal structures of related compounds, see: Fun et al. (2008 [triangle]); Singh & Singh (2010 [triangle]); Ahmad et al. (2010 [triangle]); Tang (2010 [triangle]). For reference bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3063-scheme1.jpg

Experimental

Crystal data

  • C15H12Cl2N2O
  • M r = 307.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3063-efi1.jpg
  • a = 7.563 (1) Å
  • b = 25.729 (2) Å
  • c = 8.174 (2) Å
  • β = 115.771 (2)°
  • V = 1432.4 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.45 mm−1
  • T = 298 K
  • 0.15 × 0.13 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.936, T max = 0.957
  • 7436 measured reflections
  • 3040 independent reflections
  • 1529 reflections with I > 2σ(I)
  • R int = 0.089

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.097
  • S = 0.85
  • 3040 reflections
  • 185 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043710/wn2414sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043710/wn2414Isup2.hkl

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

Acknowledgments

Financial support from the Jiaying University Research Fund is gratefully acknowledged.

supplementary crystallographic information

Comment

Hydrazone compounds have received much attention in biological and structural chemistry in the last few years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). In the present paper, the author reports the crystal structure of the new title hydrazone compound (Fig. 1).

In the title molecule, the dihedral angle between the two benzene rings is 12.2 (2)°. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8 and N1—N2—C8—C9 are 3.1 (2), 12.2 (2), and 3.0 (2)°, respectively. All the bond lengths have normal values (Allen et al., 1987) and are comparable to those in the similar hydrazone compound reported recently (Tang, 2010).

In the crystal structure of the title compound, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the c axis (Fig. 2).

Experimental

2,4-Dichlorobenzaldehyde (0.1 mmol, 19.1 mg) and 2-methylbenzohydrazide (0.1 mmol, 15.0 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless block-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

Refinement

Atom H2 was located in a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å [Uiso(H) = 0.08 Å2]. Other H atoms were constrained to ideal geometries and refined as riding, with Csp2—H = 0.93 Å and C(methyl)—H = 0.96 Å; Uiso(H) = kUeq(C), where k = 1.5 for methyl H and 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radius.
Fig. 2.
Molecular packing of the title compound, with hydrogen bonds shown as dashed lines.

Crystal data

C15H12Cl2N2OF(000) = 632
Mr = 307.17Dx = 1.424 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.563 (1) ÅCell parameters from 1160 reflections
b = 25.729 (2) Åθ = 2.7–24.3°
c = 8.174 (2) ŵ = 0.45 mm1
β = 115.771 (2)°T = 298 K
V = 1432.4 (4) Å3Block, colourless
Z = 40.15 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer3040 independent reflections
Radiation source: fine-focus sealed tube1529 reflections with I > 2σ(I)
graphiteRint = 0.089
ω scansθmax = 27.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→6
Tmin = 0.936, Tmax = 0.957k = −32→28
7436 measured reflectionsl = −10→10

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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 0.85w = 1/[σ2(Fo2) + (0.0246P)2] where P = (Fo2 + 2Fc2)/3
3040 reflections(Δ/σ)max < 0.001
185 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = −0.18 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
Cl10.30785 (12)0.05472 (3)0.66289 (10)0.0762 (3)
Cl2−0.23133 (11)0.02731 (3)−0.01806 (10)0.0694 (3)
H20.424 (4)0.2371 (10)0.803 (2)0.080*
N10.3080 (3)0.21618 (9)0.5418 (2)0.0400 (5)
N20.4152 (3)0.24626 (9)0.6931 (3)0.0412 (6)
O10.4719 (3)0.30767 (7)0.5227 (2)0.0506 (5)
C10.1513 (3)0.13548 (10)0.4312 (3)0.0354 (6)
C20.1547 (3)0.08202 (11)0.4558 (3)0.0411 (7)
C30.0400 (4)0.04854 (11)0.3178 (3)0.0455 (7)
H30.04740.01280.33630.055*
C4−0.0840 (3)0.06916 (12)0.1541 (3)0.0422 (7)
C5−0.0965 (4)0.12162 (12)0.1234 (3)0.0473 (7)
H5−0.18320.13500.01140.057*
C60.0214 (4)0.15428 (11)0.2613 (3)0.0438 (7)
H60.01420.18990.24030.053*
C70.2715 (3)0.17057 (11)0.5775 (3)0.0392 (7)
H70.32150.15950.69760.047*
C80.4929 (4)0.29150 (10)0.6711 (3)0.0375 (6)
C90.6141 (4)0.31927 (10)0.8446 (3)0.0367 (6)
C100.5972 (4)0.37312 (11)0.8577 (3)0.0419 (7)
C110.7197 (5)0.39632 (12)1.0223 (4)0.0587 (8)
H110.70960.43201.03530.070*
C120.8536 (5)0.36888 (15)1.1652 (4)0.0649 (9)
H120.93440.38591.27200.078*
C130.8691 (4)0.31614 (14)1.1512 (4)0.0601 (9)
H130.96020.29721.24820.072*
C140.7481 (4)0.29148 (11)0.9917 (3)0.0472 (7)
H140.75640.25560.98270.057*
C150.4557 (4)0.40581 (11)0.7048 (4)0.0604 (9)
H15A0.43800.43860.75160.091*
H15B0.33170.38820.64750.091*
H15C0.50680.41150.61740.091*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0772 (6)0.0571 (6)0.0563 (5)−0.0056 (4)−0.0065 (4)0.0130 (4)
Cl20.0518 (5)0.0768 (6)0.0616 (5)−0.0099 (4)0.0080 (4)−0.0297 (4)
N10.0466 (14)0.0428 (15)0.0341 (12)−0.0087 (12)0.0208 (10)−0.0055 (11)
N20.0559 (14)0.0402 (15)0.0316 (12)−0.0128 (12)0.0229 (12)−0.0057 (11)
O10.0797 (14)0.0437 (13)0.0342 (10)−0.0083 (10)0.0301 (10)0.0013 (8)
C10.0309 (14)0.0418 (18)0.0359 (15)−0.0042 (13)0.0169 (12)−0.0042 (12)
C20.0340 (15)0.0457 (19)0.0390 (15)−0.0025 (13)0.0116 (12)−0.0008 (13)
C30.0380 (16)0.0406 (19)0.0550 (17)−0.0034 (13)0.0175 (14)−0.0038 (14)
C40.0309 (15)0.051 (2)0.0421 (16)−0.0033 (13)0.0134 (13)−0.0131 (14)
C50.0403 (16)0.062 (2)0.0339 (15)0.0094 (15)0.0113 (13)−0.0041 (14)
C60.0496 (17)0.0418 (19)0.0391 (16)0.0049 (14)0.0185 (14)0.0018 (13)
C70.0411 (16)0.0446 (19)0.0303 (14)−0.0041 (14)0.0139 (12)−0.0009 (13)
C80.0429 (16)0.0371 (18)0.0369 (15)0.0020 (13)0.0213 (13)−0.0031 (13)
C90.0420 (16)0.0399 (19)0.0355 (15)−0.0059 (13)0.0236 (13)−0.0013 (12)
C100.0492 (17)0.0383 (19)0.0520 (17)−0.0061 (14)0.0348 (15)−0.0031 (14)
C110.076 (2)0.050 (2)0.066 (2)−0.0191 (18)0.046 (2)−0.0198 (18)
C120.074 (2)0.079 (3)0.0475 (19)−0.032 (2)0.0317 (19)−0.0183 (19)
C130.056 (2)0.077 (3)0.0438 (18)−0.0152 (18)0.0183 (16)0.0042 (17)
C140.0507 (17)0.0504 (19)0.0431 (16)−0.0092 (15)0.0228 (14)−0.0014 (15)
C150.065 (2)0.043 (2)0.079 (2)0.0056 (16)0.0376 (19)0.0034 (17)

Geometric parameters (Å, °)

Cl1—C21.731 (2)C7—H70.9300
Cl2—C41.737 (2)C8—C91.494 (3)
N1—C71.268 (3)C9—C141.387 (3)
N1—N21.383 (3)C9—C101.400 (3)
N2—C81.351 (3)C10—C111.393 (4)
N2—H20.901 (10)C10—C151.501 (4)
O1—C81.226 (3)C11—C121.364 (4)
C1—C21.389 (3)C11—H110.9300
C1—C61.393 (3)C12—C131.371 (4)
C1—C71.458 (3)C12—H120.9300
C2—C31.384 (3)C13—C141.379 (3)
C3—C41.364 (3)C13—H130.9300
C3—H30.9300C14—H140.9300
C4—C51.368 (3)C15—H15A0.9600
C5—C61.377 (3)C15—H15B0.9600
C5—H50.9300C15—H15C0.9600
C6—H60.9300
C7—N1—N2114.4 (2)O1—C8—C9122.6 (2)
C8—N2—N1118.9 (2)N2—C8—C9114.1 (2)
C8—N2—H2120.6 (18)C14—C9—C10120.0 (2)
N1—N2—H2120.3 (18)C14—C9—C8119.5 (2)
C2—C1—C6116.7 (2)C10—C9—C8120.5 (2)
C2—C1—C7121.9 (2)C11—C10—C9116.9 (3)
C6—C1—C7121.4 (3)C11—C10—C15119.9 (3)
C3—C2—C1122.2 (2)C9—C10—C15123.2 (2)
C3—C2—Cl1117.4 (2)C12—C11—C10122.7 (3)
C1—C2—Cl1120.39 (19)C12—C11—H11118.7
C4—C3—C2118.5 (3)C10—C11—H11118.7
C4—C3—H3120.7C11—C12—C13120.0 (3)
C2—C3—H3120.7C11—C12—H12120.0
C3—C4—C5121.8 (2)C13—C12—H12120.0
C3—C4—Cl2118.6 (2)C12—C13—C14119.2 (3)
C5—C4—Cl2119.6 (2)C12—C13—H13120.4
C4—C5—C6118.9 (2)C14—C13—H13120.4
C4—C5—H5120.5C13—C14—C9121.1 (3)
C6—C5—H5120.5C13—C14—H14119.4
C5—C6—C1121.9 (3)C9—C14—H14119.4
C5—C6—H6119.0C10—C15—H15A109.5
C1—C6—H6119.0C10—C15—H15B109.5
N1—C7—C1120.3 (2)H15A—C15—H15B109.5
N1—C7—H7119.9C10—C15—H15C109.5
C1—C7—H7119.9H15A—C15—H15C109.5
O1—C8—N2123.2 (2)H15B—C15—H15C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.90 (1)2.03 (1)2.892 (3)159 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2414).

References

  • Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976. [PMC free article] [PubMed]
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