organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: cuichuansheng@lcu.edu.cn

(Received 28 August 2009; accepted 9 September 2009; online 16 September 2009)

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[Bedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253-1261.]). For related crystal structures, see: Fun et al. (2008[Fun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594-o1595.]); Alhadi et al. (2008[Alhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584.]); Nie (2008[Nie, Y. (2008). Acta Cryst. E64, o471.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17N3O

  • Mr = 267.33

  • Orthorhombic, P 21 21 21

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.968, Tmax = 0.988

  • 6499 measured reflections

  • 1489 independent reflections

  • 768 reflections with I > 2σ(I)

  • Rint = 0.072

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O1i 0.86 2.19 2.982 (4) 153
Symmetry code: (i) x+1, y, z.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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. The molecular structure of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.
N'-[4-(Dimethylamino)benzylidene]benzohydrazide top
Crystal data top
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 top
Bruker SMART APEX CCD area-detector
diffractometer
1489 independent reflections
Radiation source: fine-focus sealed tube768 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.072
ϕ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 65
Tmin = 0.968, Tmax = 0.988k = 105
6499 measured reflectionsl = 3837
Refinement top
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 = 1.00 w = 1/[σ2(Fo2)]
1489 reflections(Δ/σ)max = 0.045
183 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.11 e Å3
Crystal data top
C16H17N3OV = 1408.5 (13) Å3
Mr = 267.33Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.131 (3) ŵ = 0.08 mm1
b = 8.446 (4) ÅT = 298 K
c = 32.502 (16) Å0.40 × 0.31 × 0.15 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1489 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
768 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.988Rint = 0.072
6499 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.066H-atom parameters constrained
S = 1.00Δρmax = 0.13 e Å3
1489 reflectionsΔρmin = 0.11 e Å3
183 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
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)
H110.71360.63580.02350.094*
C121.0201 (9)0.4892 (5)0.02920 (12)0.0674 (11)
C131.2002 (8)0.4120 (5)0.00492 (13)0.0843 (13)
H131.32290.34620.01720.101*
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)
H15A1.21640.27400.07770.189*
H15B1.37250.42570.09060.189*
H15C1.15680.35740.11980.189*
C160.8855 (10)0.5890 (4)0.09662 (11)0.1149 (18)
H16A0.70580.59680.08870.172*
H16B0.89630.55840.12500.172*
H16C0.96900.68970.09290.172*
Atomic displacement parameters (Å2) top
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, º) top
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, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.192.982 (4)153
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC16H17N3O
Mr267.33
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)5.131 (3), 8.446 (4), 32.502 (16)
V3)1408.5 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.31 × 0.15
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.968, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
6499, 1489, 768
Rint0.072
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.066, 1.00
No. of reflections1489
No. of parameters183
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.11

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.192.982 (4)152.5
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

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

References

First citationAlhadi, A. A., Ali, H. M., Puvaneswary, S., Robinson, W. T. & Ng, S. W. (2008). Acta Cryst. E64, o1584.  Web of Science CSD CrossRef IUCr Journals
First citationBedia, K. K., Elcin, O., Seda, U., Fatma, K., Nathaly, S., Sevim, R. & Dimoglo, A. (2006). Eur. J. Med. Chem. 41, 1253–1261.  Web of Science CrossRef PubMed CAS
First citationFun, H.-K., Patil, P. S., Jebas, S. R., Sujith, K. V. & Kalluraya, B. (2008). Acta Cryst. E64, o1594–o1595.  Web of Science CSD CrossRef IUCr Journals
First citationNie, Y. (2008). Acta Cryst. E64, o471.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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