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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2472.
Published online 2009 September 16. doi:  10.1107/S1600536809036460
PMCID: PMC2970421

N′-[4-(Dimethyl­amino)benzyl­idene]benzohydrazide

Abstract

In the title mol­ecule, C16H17N3O, the two aromatic rings form a dihedral angle of 4.51 (18)°. In the crystal structure, inter­molecular N—H(...)O hydrogen bonds link mol­ecules related by translation along the a axis into ribbons.

Related literature

For the biological properties of Schiff base ligands, see Bedia et al. (2006 [triangle]). For related crystal structures, see: Fun et al. (2008 [triangle]); Alhadi et al. (2008 [triangle]); Nie (2008 [triangle]).

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Object name is e-65-o2472-scheme1.jpg

Experimental

Crystal data

  • C16H17N3O
  • M r = 267.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2472-efi1.jpg
  • a = 5.131 (3) Å
  • b = 8.446 (4) Å
  • c = 32.502 (16) Å
  • V = 1408.5 (13) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 K
  • 0.40 × 0.31 × 0.15 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.968, T max = 0.988
  • 6499 measured reflections
  • 1489 independent reflections
  • 768 reflections with I > 2σ(I)
  • R int = 0.072

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.066
  • S = 1.00
  • 1489 reflections
  • 183 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.11 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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 I, global. DOI: 10.1107/S1600536809036460/cv2609sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036460/cv2609Isup2.hkl

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

Acknowledgments

The authors acknowledge the financial support of the University Student Science and Technology Culture Foundation of Liaocheng University (grant No. SRT08041HX2).

supplementary crystallographic information

Comment

Schiff base ligands have received considerable attention during the last decades, mainly because of their structures or for their biological properties (Bedia et al., 2006). We report here the crystal structure of the title new Schiff base compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to the values observed in similar compounds (Nie et al., 2008; Fun et al., 2008; Alhadi et al., 2008). The dihedral angle between the two aromatic rings in the Schiff base molecule is 4.51 (18) °, indicating that two these rings are approximately coplanar.

Weak intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along axis a into ribbons.

Experimental

Benzohydrazide (5.0 mmol), 20 ml ethanol and 4-(dimethylamino)benzaldehyde (5.0 mmol) were mixed in 50 ml flash. After refluxing 3 h, the resulting mixture was cooled to room temperature, and recrystalized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C16H17N3O: C 71.89, H 6.41, N 15.72%; found: C 71.63, H 6.55, N 15.64%.

Refinement

All H atoms were placed in geometrically idealized positions (N—H 0.86 and C—H = 0.93–0.96 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2–1.5 Ueq(C, N). In the absence of any significant anomalous scatterers in the molecule, 1489 Friedel pairs were merged before the final refinement.

Figures

Fig. 1.
The molecular structure of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.

Crystal data

C16H17N3ODx = 1.261 Mg m3
Mr = 267.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 731 reflections
a = 5.131 (3) Åθ = 2.5–19.0°
b = 8.446 (4) ŵ = 0.08 mm1
c = 32.502 (16) ÅT = 298 K
V = 1408.5 (13) Å3Block, red
Z = 40.40 × 0.31 × 0.15 mm
F(000) = 568

Data collection

Bruker SMART APEX CCD area-detector diffractometer1489 independent reflections
Radiation source: fine-focus sealed tube768 reflections with I > 2σ(I)
graphiteRint = 0.072
[var phi] and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −6→5
Tmin = 0.968, Tmax = 0.988k = −10→5
6499 measured reflectionsl = −38→37

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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2)]
1489 reflections(Δ/σ)max = 0.045
183 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.11 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
N10.8782 (6)0.6093 (3)0.16374 (9)0.0668 (9)
H11.03230.60000.17380.080*
N20.8356 (6)0.5902 (4)0.12192 (9)0.0661 (9)
N31.0131 (7)0.4725 (4)−0.07166 (10)0.0921 (12)
O10.4487 (5)0.6576 (3)0.17584 (7)0.0753 (8)
C10.6729 (8)0.6429 (4)0.18839 (11)0.0584 (11)
C20.7361 (7)0.6580 (4)0.23326 (10)0.0527 (10)
C30.9403 (7)0.5772 (4)0.25149 (12)0.0708 (12)
H31.05000.51490.23550.085*
C40.9818 (8)0.5887 (5)0.29326 (12)0.0841 (13)
H41.11660.53210.30550.101*
C50.8242 (9)0.6838 (5)0.31681 (12)0.0825 (13)
H50.85570.69440.34480.099*
C60.6207 (9)0.7630 (4)0.29898 (12)0.0778 (13)
H60.51190.82590.31500.093*
C70.5770 (8)0.7494 (4)0.25716 (12)0.0696 (12)
H70.43790.80290.24520.084*
C81.0327 (7)0.5383 (4)0.10171 (11)0.0650 (12)
H81.18400.51080.11570.078*
C91.0231 (7)0.5218 (4)0.05744 (11)0.0597 (11)
C100.8437 (8)0.5959 (4)0.03323 (11)0.0690 (11)
H100.71800.65880.04580.083*
C110.8400 (9)0.5818 (4)−0.00856 (11)0.0784 (12)
H110.71360.6358−0.02350.094*
C121.0201 (9)0.4892 (5)−0.02920 (12)0.0674 (11)
C131.2002 (8)0.4120 (5)−0.00492 (13)0.0843 (13)
H131.32290.3462−0.01720.101*
C141.2020 (7)0.4303 (5)0.03710 (12)0.0813 (14)
H141.32970.37860.05230.098*
C151.2059 (9)0.3741 (5)−0.09163 (11)0.1262 (19)
H15A1.21640.2740−0.07770.189*
H15B1.37250.4257−0.09060.189*
H15C1.15680.3574−0.11980.189*
C160.8855 (10)0.5890 (4)−0.09662 (11)0.1149 (18)
H16A0.70580.5968−0.08870.172*
H16B0.89630.5584−0.12500.172*
H16C0.96900.6897−0.09290.172*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.052 (2)0.097 (2)0.052 (2)0.0054 (19)−0.0077 (19)0.0059 (18)
N20.062 (2)0.089 (2)0.047 (2)−0.001 (2)−0.0067 (19)−0.0006 (18)
N30.124 (3)0.094 (3)0.058 (2)−0.008 (3)0.015 (3)−0.004 (2)
O10.0489 (16)0.110 (2)0.0666 (17)0.0048 (17)−0.0071 (16)0.0070 (15)
C10.052 (3)0.063 (3)0.060 (3)−0.001 (3)0.000 (3)0.004 (2)
C20.051 (3)0.060 (3)0.047 (2)−0.004 (2)0.001 (2)0.001 (2)
C30.053 (3)0.097 (3)0.063 (3)0.013 (2)0.001 (2)0.012 (2)
C40.074 (3)0.117 (4)0.062 (3)0.008 (3)−0.015 (3)0.006 (3)
C50.086 (3)0.104 (4)0.058 (3)−0.010 (3)0.002 (3)0.000 (3)
C60.086 (4)0.082 (3)0.066 (3)0.012 (3)0.007 (3)−0.007 (2)
C70.072 (3)0.068 (3)0.069 (3)0.015 (3)0.003 (3)0.005 (2)
C80.055 (3)0.083 (3)0.057 (3)0.010 (3)−0.003 (2)0.005 (2)
C90.053 (3)0.079 (3)0.047 (2)0.003 (3)0.005 (2)0.005 (2)
C100.070 (3)0.075 (3)0.062 (3)0.015 (3)0.004 (3)−0.004 (2)
C110.091 (3)0.089 (3)0.056 (3)0.009 (3)−0.006 (3)0.007 (2)
C120.078 (3)0.069 (3)0.056 (3)−0.006 (3)0.012 (3)0.005 (2)
C130.081 (3)0.097 (3)0.075 (3)0.021 (3)0.020 (3)−0.002 (3)
C140.067 (3)0.111 (4)0.066 (3)0.032 (3)0.002 (3)0.006 (3)
C150.112 (4)0.196 (5)0.071 (3)−0.019 (4)0.028 (3)−0.033 (3)
C160.180 (5)0.099 (4)0.066 (3)−0.018 (4)−0.021 (3)0.014 (3)

Geometric parameters (Å, °)

N1—C11.353 (4)C7—H70.9300
N1—N21.386 (3)C8—C91.446 (4)
N1—H10.8600C8—H80.9300
N2—C81.283 (4)C9—C101.363 (4)
N3—C121.388 (4)C9—C141.370 (4)
N3—C161.433 (4)C10—C111.363 (4)
N3—C151.446 (4)C10—H100.9300
O1—C11.227 (4)C11—C121.384 (5)
C1—C21.499 (4)C11—H110.9300
C2—C71.366 (4)C12—C131.379 (4)
C2—C31.384 (4)C13—C141.374 (4)
C3—C41.378 (4)C13—H130.9300
C3—H30.9300C14—H140.9300
C4—C51.373 (4)C15—H15A0.9600
C4—H40.9300C15—H15B0.9600
C5—C61.369 (5)C15—H15C0.9600
C5—H50.9300C16—H16A0.9600
C6—C71.382 (4)C16—H16B0.9600
C6—H60.9300C16—H16C0.9600
C1—N1—N2118.8 (3)C10—C9—C14115.6 (4)
C1—N1—H1120.6C10—C9—C8123.6 (4)
N2—N1—H1120.6C14—C9—C8120.8 (4)
C8—N2—N1114.7 (3)C11—C10—C9123.0 (4)
C12—N3—C16120.3 (4)C11—C10—H10118.5
C12—N3—C15119.2 (4)C9—C10—H10118.5
C16—N3—C15116.9 (4)C10—C11—C12121.5 (4)
O1—C1—N1123.7 (3)C10—C11—H11119.2
O1—C1—C2121.1 (4)C12—C11—H11119.2
N1—C1—C2115.2 (3)C11—C12—C13115.9 (4)
C7—C2—C3119.2 (3)C11—C12—N3121.5 (4)
C7—C2—C1118.2 (4)C13—C12—N3122.5 (4)
C3—C2—C1122.6 (4)C14—C13—C12121.3 (4)
C4—C3—C2120.3 (4)C14—C13—H13119.4
C4—C3—H3119.9C12—C13—H13119.4
C2—C3—H3119.9C9—C14—C13122.6 (4)
C5—C4—C3120.0 (4)C9—C14—H14118.7
C5—C4—H4120.0C13—C14—H14118.7
C3—C4—H4120.0N3—C15—H15A109.5
C6—C5—C4120.0 (4)N3—C15—H15B109.5
C6—C5—H5120.0H15A—C15—H15B109.5
C4—C5—H5120.0N3—C15—H15C109.5
C5—C6—C7120.0 (4)H15A—C15—H15C109.5
C5—C6—H6120.0H15B—C15—H15C109.5
C7—C6—H6120.0N3—C16—H16A109.5
C2—C7—C6120.6 (4)N3—C16—H16B109.5
C2—C7—H7119.7H16A—C16—H16B109.5
C6—C7—H7119.7N3—C16—H16C109.5
N2—C8—C9121.0 (4)H16A—C16—H16C109.5
N2—C8—H8119.5H16B—C16—H16C109.5
C9—C8—H8119.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.192.982 (4)153

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2609).

References

  • Alhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584. [PMC free article] [PubMed]
  • Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem.41, 1253–1261. [PubMed]
  • Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595. [PMC free article] [PubMed]
  • Nie, Y. (2008). Acta Cryst. E64, o471. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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