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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2729–o2730.
Published online 2010 October 9. doi:  10.1107/S1600536810038857
PMCID: PMC3009357

4-Chloro-N′-(4-meth­oxy­benzyl­idene)benzohydrazide methanol monosolvate

Abstract

The title compound, C15H13ClN2O2·CH4O, consists of a 4-chloro-N′-(4-meth­oxy­benzyl­idene)benzohydrazide (CMB) mol­ecule and a methanol mol­ecule of crystallization. It was obtained by the condensation of 4-meth­oxy­benzaldehyde with 4-chloro­benzohydrazide. In the CMB mol­ecule, the dihedral angle between the two benzene rings is 50.1 (3)°. The methanol mol­ecule is linked to the CMB mol­ecule through O—H(...)O and O—H(...)N hydrogen bonds. In the crystal, CMB mol­ecules are linked through inter­molecular N—H(...)O hydrogen bonds, involving the methanol mol­ecule, forming chains propagating along [010].

Related literature

For background to compounds obtained by the condensation of aldehydes with benzohydrazides, see: Qiu & Zhao (2008 [triangle]); Yathirajan et al. (2007 [triangle]); Salhin et al. (2007 [triangle]). For their biological properties, see: Bedia et al. (2006 [triangle]); Terzioglu & Gürsoy (2003 [triangle]); Küçükgüzel et al. (2003 [triangle]); Charkoudian et al. (2007 [triangle]). For similar compounds reported by our group, see: Huang (2009 [triangle]); Wu (2009 [triangle]). For other similar structures, see: Fun et al. (2008 [triangle]); Liu & Li (2004 [triangle]); Lei et al. (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2729-scheme1.jpg

Experimental

Crystal data

  • C15H13ClN2O2·CH4O
  • M r = 320.77
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2729-efi1.jpg
  • a = 10.914 (3) Å
  • b = 6.459 (2) Å
  • c = 11.358 (2) Å
  • β = 93.000 (3)°
  • V = 799.6 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 298 K
  • 0.17 × 0.13 × 0.12 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.958, T max = 0.970
  • 6424 measured reflections
  • 1865 independent reflections
  • 1030 reflections with I > 2σ(I)
  • R int = 0.074

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.123
  • S = 1.00
  • 1865 reflections
  • 201 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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/S1600536810038857/su2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038857/su2215Isup2.hkl

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

Acknowledgments

This work was supported by Qiqihar Medical University.

supplementary crystallographic information

Comment

In the last few years considerable attention has been focused on compounds derived from the condensation of aldehydes with benzohydrazides, especially for their crystal structures (Lei et al., 2008; Qiu & Zhao, 2008; Yathirajan et al., 2007; Salhin et al., 2007; Fun et al., 2008; Liu & Li, 2004) or for their biological properties (Bedia et al., 2006; Terzioglu & Gürsoy, 2003; Küçükgüzel et al., 2003; Charkoudian et al., 2007). Continueing our research on the synthesis and crystal structures of such compounds (Huang, 2009; Wu, 2009), herein we report on the crystal structure of the title compound, obtained by the condensation of 4-methoxybenzaldehyde with 4-chlorobenzohydrazide.

The title compound consists of a 4-chloro-N'-(4-methoxybenzylidene)benzohydrazide (CMB) molecule and a methanol solvent molecule (Fig. 1). The methanol molecule is linked to the CMB molecule through intermolecular O—H···O and O—H···N hydrogen bonds (Table 1). In the CMB molecule the dihedral angle between the two benzene rings is 50.1 (3)°. The bond distances (Allen et al., 1987) and bond angles are normal and similar to those reported for the above mentioned compounds.

In the crystal molecules are linked, via the methanol molecule, through intermolecular N—H···O hydrogen bonds (Table 1), so forming chains propagating along the b axis (Fig. 2).

Experimental

The title compound was prepared by the condensation of 4-methoxybenzaldehyde (0.1 mol) and 4-chlorobenzohydrazide (0.1 mol) in ethanol (20 ml). The excess ethanol was removed by distillation. The colou; rless solid obtained was filtered and washed with ethanol. Single crystals, suitable for X-ray diffraction, were obtained on slow evaporation of a solution of the title compound in methanol.

Refinement

As there is no asymmetric center in the title molecule in the final cycles of least-squares refinement 1371 Friedel pairs were merged and Δf" set to zero, rather than refining the structure as a inversion twin. The H-atoms were positioned geometrically and treated as riding atoms: O—H = 0.82 Å, N—H = 0.86 Å, C—H = 0.93 and 0.96 Å, for CH and CH3 H-atoms, respectively, with Uiso(H) = k × Ueq(O–, N–, C-parent atom), where k = 1.5 for OH and CH3 H-atoms and k = 1.2 for all other H-atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
Fig. 2.
The crystal packing of the title compound viewed along the c axis. Hydrogen bonds are shown as dashed lines - see Table 1 for details (H-atoms not involved in hydrogen bonding have been omitted for clarity).

Crystal data

C15H13ClN2O2·CH4OF(000) = 336
Mr = 320.77Dx = 1.332 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 640 reflections
a = 10.914 (3) Åθ = 2.5–24.3°
b = 6.459 (2) ŵ = 0.25 mm1
c = 11.358 (2) ÅT = 298 K
β = 93.000 (3)°Block, colorless
V = 799.6 (4) Å30.17 × 0.13 × 0.12 mm
Z = 2

Data collection

Bruker APEXII CCD area-detector diffractometer1865 independent reflections
Radiation source: fine-focus sealed tube1030 reflections with I > 2σ(I)
graphiteRint = 0.074
ω scansθmax = 27.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.958, Tmax = 0.970k = −7→8
6424 measured reflectionsl = −14→14

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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3
1865 reflections(Δ/σ)max < 0.001
201 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = −0.19 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
Cl10.58789 (14)1.0709 (3)1.25398 (13)0.0754 (6)
O10.7358 (4)0.4112 (6)0.8320 (3)0.0689 (13)
O21.0029 (3)0.3682 (6)0.1329 (3)0.0573 (11)
N10.7495 (4)0.7047 (7)0.7275 (4)0.0502 (12)
H10.74470.83760.72570.060*
N20.7810 (4)0.5948 (7)0.6283 (4)0.0493 (12)
C10.6292 (5)0.9354 (10)1.1301 (5)0.0505 (15)
C20.6174 (5)1.0320 (9)1.0215 (5)0.0571 (16)
H20.58861.16731.01560.069*
C30.6487 (5)0.9259 (9)0.9215 (5)0.0559 (15)
H3A0.64020.99080.84840.067*
C40.6922 (4)0.7256 (8)0.9284 (5)0.0395 (13)
C50.7063 (5)0.6364 (9)1.0389 (5)0.0561 (16)
H50.73930.50391.04560.067*
C60.6732 (5)0.7365 (10)1.1399 (5)0.0592 (17)
H60.68050.67081.21280.071*
C70.7264 (5)0.5997 (10)0.8265 (5)0.0500 (14)
C80.8292 (5)0.7001 (9)0.5487 (5)0.0482 (15)
H80.83900.84180.56050.058*
C90.8700 (4)0.6108 (9)0.4395 (4)0.0424 (13)
C100.9473 (5)0.7190 (8)0.3688 (5)0.0482 (14)
H100.97000.85320.39010.058*
C110.9914 (5)0.6360 (9)0.2693 (5)0.0504 (15)
H111.04490.71160.22480.060*
C120.9561 (5)0.4384 (9)0.2346 (5)0.0441 (14)
C130.8792 (5)0.3255 (8)0.3021 (4)0.0448 (14)
H130.85580.19250.27910.054*
C140.8365 (5)0.4103 (9)0.4045 (5)0.0492 (15)
H140.78520.33290.45030.059*
C150.9668 (6)0.1704 (10)0.0893 (5)0.076 (2)
H15A0.98270.06820.14960.115*
H15B1.01250.13720.02180.115*
H15C0.88070.17180.06700.115*
O30.7025 (4)0.1217 (6)0.6473 (4)0.0689 (12)
H30.72360.23460.67450.103*
C160.5831 (6)0.1364 (13)0.5954 (5)0.092 (2)
H16A0.57720.25650.54560.139*
H16B0.52540.14810.65600.139*
H16C0.56510.01470.54910.139*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0776 (11)0.0881 (14)0.0620 (10)−0.0048 (11)0.0168 (8)−0.0320 (10)
O10.111 (4)0.035 (2)0.063 (3)0.008 (3)0.018 (2)−0.002 (2)
O20.074 (3)0.051 (3)0.049 (2)0.004 (2)0.024 (2)−0.004 (2)
N10.069 (3)0.030 (3)0.052 (3)0.004 (2)0.014 (2)−0.009 (2)
N20.064 (3)0.035 (3)0.050 (3)0.003 (3)0.011 (2)−0.006 (3)
C10.041 (3)0.065 (4)0.046 (4)−0.003 (3)0.006 (3)−0.023 (3)
C20.065 (4)0.044 (4)0.064 (4)0.000 (3)0.018 (3)−0.009 (3)
C30.075 (4)0.038 (3)0.056 (4)0.004 (3)0.017 (3)0.001 (3)
C40.044 (3)0.034 (3)0.040 (3)0.001 (3)0.004 (3)−0.008 (3)
C50.053 (4)0.048 (4)0.068 (4)0.014 (3)0.004 (3)0.003 (3)
C60.055 (4)0.071 (5)0.052 (4)0.009 (4)0.007 (3)0.001 (4)
C70.054 (4)0.042 (4)0.054 (4)0.004 (3)0.008 (3)0.001 (3)
C80.058 (4)0.033 (3)0.054 (4)0.001 (3)0.002 (3)−0.007 (3)
C90.047 (3)0.038 (3)0.041 (3)0.002 (3)−0.001 (3)−0.004 (3)
C100.056 (4)0.034 (3)0.054 (4)−0.008 (3)0.000 (3)0.003 (3)
C110.059 (4)0.045 (4)0.048 (4)−0.003 (3)0.010 (3)0.007 (3)
C120.046 (3)0.045 (4)0.041 (3)0.006 (3)−0.002 (3)−0.001 (3)
C130.057 (4)0.035 (3)0.044 (3)−0.008 (3)0.010 (3)−0.008 (3)
C140.060 (4)0.037 (3)0.051 (4)−0.007 (3)0.009 (3)−0.001 (3)
C150.102 (6)0.058 (5)0.071 (5)0.001 (4)0.017 (4)−0.022 (4)
O30.095 (3)0.031 (3)0.080 (3)0.005 (2)0.003 (2)−0.006 (2)
C160.102 (6)0.087 (6)0.087 (5)−0.001 (5)−0.004 (4)−0.013 (5)

Geometric parameters (Å, °)

Cl1—C11.736 (5)C8—H80.9300
O1—C71.224 (7)C9—C101.384 (7)
O2—C121.364 (6)C9—C141.398 (8)
O2—C151.419 (7)C10—C111.362 (7)
N1—C71.349 (6)C10—H100.9300
N1—N21.389 (5)C11—C121.385 (7)
N1—H10.8600C11—H110.9300
N2—C81.268 (6)C12—C131.375 (7)
C1—C61.374 (8)C13—C141.389 (6)
C1—C21.383 (7)C13—H130.9300
C2—C31.384 (7)C14—H140.9300
C2—H20.9300C15—H15A0.9600
C3—C41.379 (7)C15—H15B0.9600
C3—H3A0.9300C15—H15C0.9600
C4—C51.383 (7)O3—C161.406 (6)
C4—C71.477 (7)O3—H30.8200
C5—C61.381 (7)C16—H16A0.9600
C5—H50.9300C16—H16B0.9600
C6—H60.9300C16—H16C0.9600
C8—C91.458 (7)
C12—O2—C15119.0 (4)C10—C9—C8121.1 (5)
C7—N1—N2119.0 (4)C14—C9—C8121.4 (5)
C7—N1—H1120.5C11—C10—C9122.4 (5)
N2—N1—H1120.5C11—C10—H10118.8
C8—N2—N1115.7 (5)C9—C10—H10118.8
C6—C1—C2120.6 (5)C10—C11—C12119.6 (5)
C6—C1—Cl1120.7 (5)C10—C11—H11120.2
C2—C1—Cl1118.7 (5)C12—C11—H11120.2
C1—C2—C3119.6 (6)O2—C12—C13124.2 (5)
C1—C2—H2120.2O2—C12—C11115.9 (5)
C3—C2—H2120.2C13—C12—C11119.9 (5)
C4—C3—C2121.1 (6)C12—C13—C14120.0 (5)
C4—C3—H3A119.4C12—C13—H13120.0
C2—C3—H3A119.4C14—C13—H13120.0
C3—C4—C5117.6 (5)C13—C14—C9120.6 (5)
C3—C4—C7124.9 (5)C13—C14—H14119.7
C5—C4—C7117.5 (5)C9—C14—H14119.7
C6—C5—C4122.5 (5)O2—C15—H15A109.5
C6—C5—H5118.7O2—C15—H15B109.5
C4—C5—H5118.7H15A—C15—H15B109.5
C1—C6—C5118.4 (6)O2—C15—H15C109.5
C1—C6—H6120.8H15A—C15—H15C109.5
C5—C6—H6120.8H15B—C15—H15C109.5
O1—C7—N1121.6 (5)C16—O3—H3109.5
O1—C7—C4122.1 (5)O3—C16—H16A109.5
N1—C7—C4116.3 (5)O3—C16—H16B109.5
N2—C8—C9123.5 (5)H16A—C16—H16B109.5
N2—C8—H8118.3O3—C16—H16C109.5
C9—C8—H8118.3H16A—C16—H16C109.5
C10—C9—C14117.5 (5)H16B—C16—H16C109.5
C7—N1—N2—C8−164.0 (5)C5—C4—C7—N1−159.7 (5)
C6—C1—C2—C30.9 (8)N1—N2—C8—C9178.9 (4)
Cl1—C1—C2—C3−179.4 (4)N2—C8—C9—C10−164.4 (5)
C1—C2—C3—C4−0.4 (9)N2—C8—C9—C1413.1 (8)
C2—C3—C4—C5−1.5 (8)C14—C9—C10—C11−0.7 (8)
C2—C3—C4—C7179.2 (5)C8—C9—C10—C11176.9 (5)
C3—C4—C5—C63.1 (8)C9—C10—C11—C121.7 (8)
C7—C4—C5—C6−177.6 (5)C15—O2—C12—C133.0 (8)
C2—C1—C6—C50.6 (8)C15—O2—C12—C11−177.5 (5)
Cl1—C1—C6—C5−179.2 (4)C10—C11—C12—O2179.0 (5)
C4—C5—C6—C1−2.7 (9)C10—C11—C12—C13−1.5 (8)
N2—N1—C7—O12.0 (8)O2—C12—C13—C14179.9 (5)
N2—N1—C7—C4−179.4 (4)C11—C12—C13—C140.4 (8)
C3—C4—C7—O1−161.9 (5)C12—C13—C14—C90.6 (8)
C5—C4—C7—O118.8 (8)C10—C9—C14—C13−0.5 (7)
C3—C4—C7—N119.5 (8)C8—C9—C14—C13−178.1 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···N20.822.473.184 (6)146
O3—H3···O10.822.122.820 (6)143
N1—H1···O3i0.862.082.880 (6)154

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2215).

References

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