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

Cui, C.; Meng, Q.; Wang, Y.

doi:10.1107/S1600536809036460

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2472

doi:10.1107/S1600536809036460

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

Chuansheng Cui,^a ^* Qingan Meng ^a and Yong Wang ^a

^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 ). For related crystal structures, see: Fun et al. (2008 ); Alhadi et al. (2008 ); Nie (2008 ).

Experimental

Crystal data

C₁₆H₁₇N₃O
M_r = 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 ) 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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.066
S = 1.00
1489 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036460/cv2609sup1.cif

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

checkCIF report

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%.

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

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

C₁₆H₁₇N₃O	D_x = 1.261 Mg m⁻³
M_r = 267.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 731 reflections
a = 5.131 (3) Å	θ = 2.5–19.0°
b = 8.446 (4) Å	µ = 0.08 mm⁻¹
c = 32.502 (16) Å	T = 298 K
V = 1408.5 (13) Å³	Block, red
Z = 4	0.40 × 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 tube	768 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→5
T_min = 0.968, T_max = 0.988	k = −10→5
6499 measured reflections	l = −38→37

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²)]
1489 reflections	(Δ/σ)_max = 0.045
183 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₁₆H₁₇N₃O	V = 1408.5 (13) Å³
M_r = 267.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.131 (3) Å	µ = 0.08 mm⁻¹
b = 8.446 (4) Å	T = 298 K
c = 32.502 (16) Å	0.40 × 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)
T_min = 0.968, T_max = 0.988	R_int = 0.072
6499 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.00	Δρ_max = 0.13 e Å⁻³
1489 reflections	Δρ_min = −0.11 e Å⁻³
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

	x	y	z	U_iso*/U_eq
N1	0.8782 (6)	0.6093 (3)	0.16374 (9)	0.0668 (9)
H1	1.0323	0.6000	0.1738	0.080*
N2	0.8356 (6)	0.5902 (4)	0.12192 (9)	0.0661 (9)
N3	1.0131 (7)	0.4725 (4)	−0.07166 (10)	0.0921 (12)
O1	0.4487 (5)	0.6576 (3)	0.17584 (7)	0.0753 (8)
C1	0.6729 (8)	0.6429 (4)	0.18839 (11)	0.0584 (11)
C2	0.7361 (7)	0.6580 (4)	0.23326 (10)	0.0527 (10)
C3	0.9403 (7)	0.5772 (4)	0.25149 (12)	0.0708 (12)
H3	1.0500	0.5149	0.2355	0.085*
C4	0.9818 (8)	0.5887 (5)	0.29326 (12)	0.0841 (13)
H4	1.1166	0.5321	0.3055	0.101*
C5	0.8242 (9)	0.6838 (5)	0.31681 (12)	0.0825 (13)
H5	0.8557	0.6944	0.3448	0.099*
C6	0.6207 (9)	0.7630 (4)	0.29898 (12)	0.0778 (13)
H6	0.5119	0.8259	0.3150	0.093*
C7	0.5770 (8)	0.7494 (4)	0.25716 (12)	0.0696 (12)
H7	0.4379	0.8029	0.2452	0.084*
C8	1.0327 (7)	0.5383 (4)	0.10171 (11)	0.0650 (12)
H8	1.1840	0.5108	0.1157	0.078*
C9	1.0231 (7)	0.5218 (4)	0.05744 (11)	0.0597 (11)
C10	0.8437 (8)	0.5959 (4)	0.03323 (11)	0.0690 (11)
H10	0.7180	0.6588	0.0458	0.083*
C11	0.8400 (9)	0.5818 (4)	−0.00856 (11)	0.0784 (12)
H11	0.7136	0.6358	−0.0235	0.094*
C12	1.0201 (9)	0.4892 (5)	−0.02920 (12)	0.0674 (11)
C13	1.2002 (8)	0.4120 (5)	−0.00492 (13)	0.0843 (13)
H13	1.3229	0.3462	−0.0172	0.101*
C14	1.2020 (7)	0.4303 (5)	0.03710 (12)	0.0813 (14)
H14	1.3297	0.3786	0.0523	0.098*
C15	1.2059 (9)	0.3741 (5)	−0.09163 (11)	0.1262 (19)
H15A	1.2164	0.2740	−0.0777	0.189*
H15B	1.3725	0.4257	−0.0906	0.189*
H15C	1.1568	0.3574	−0.1198	0.189*
C16	0.8855 (10)	0.5890 (4)	−0.09662 (11)	0.1149 (18)
H16A	0.7058	0.5968	−0.0887	0.172*
H16B	0.8963	0.5584	−0.1250	0.172*
H16C	0.9690	0.6897	−0.0929	0.172*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.052 (2)	0.097 (2)	0.052 (2)	0.0054 (19)	−0.0077 (19)	0.0059 (18)
N2	0.062 (2)	0.089 (2)	0.047 (2)	−0.001 (2)	−0.0067 (19)	−0.0006 (18)
N3	0.124 (3)	0.094 (3)	0.058 (2)	−0.008 (3)	0.015 (3)	−0.004 (2)
O1	0.0489 (16)	0.110 (2)	0.0666 (17)	0.0048 (17)	−0.0071 (16)	0.0070 (15)
C1	0.052 (3)	0.063 (3)	0.060 (3)	−0.001 (3)	0.000 (3)	0.004 (2)
C2	0.051 (3)	0.060 (3)	0.047 (2)	−0.004 (2)	0.001 (2)	0.001 (2)
C3	0.053 (3)	0.097 (3)	0.063 (3)	0.013 (2)	0.001 (2)	0.012 (2)
C4	0.074 (3)	0.117 (4)	0.062 (3)	0.008 (3)	−0.015 (3)	0.006 (3)
C5	0.086 (3)	0.104 (4)	0.058 (3)	−0.010 (3)	0.002 (3)	0.000 (3)
C6	0.086 (4)	0.082 (3)	0.066 (3)	0.012 (3)	0.007 (3)	−0.007 (2)
C7	0.072 (3)	0.068 (3)	0.069 (3)	0.015 (3)	0.003 (3)	0.005 (2)
C8	0.055 (3)	0.083 (3)	0.057 (3)	0.010 (3)	−0.003 (2)	0.005 (2)
C9	0.053 (3)	0.079 (3)	0.047 (2)	0.003 (3)	0.005 (2)	0.005 (2)
C10	0.070 (3)	0.075 (3)	0.062 (3)	0.015 (3)	0.004 (3)	−0.004 (2)
C11	0.091 (3)	0.089 (3)	0.056 (3)	0.009 (3)	−0.006 (3)	0.007 (2)
C12	0.078 (3)	0.069 (3)	0.056 (3)	−0.006 (3)	0.012 (3)	0.005 (2)
C13	0.081 (3)	0.097 (3)	0.075 (3)	0.021 (3)	0.020 (3)	−0.002 (3)
C14	0.067 (3)	0.111 (4)	0.066 (3)	0.032 (3)	0.002 (3)	0.006 (3)
C15	0.112 (4)	0.196 (5)	0.071 (3)	−0.019 (4)	0.028 (3)	−0.033 (3)
C16	0.180 (5)	0.099 (4)	0.066 (3)	−0.018 (4)	−0.021 (3)	0.014 (3)

Geometric parameters (Å, º) top

N1—C1	1.353 (4)	C7—H7	0.9300
N1—N2	1.386 (3)	C8—C9	1.446 (4)
N1—H1	0.8600	C8—H8	0.9300
N2—C8	1.283 (4)	C9—C10	1.363 (4)
N3—C12	1.388 (4)	C9—C14	1.370 (4)
N3—C16	1.433 (4)	C10—C11	1.363 (4)
N3—C15	1.446 (4)	C10—H10	0.9300
O1—C1	1.227 (4)	C11—C12	1.384 (5)
C1—C2	1.499 (4)	C11—H11	0.9300
C2—C7	1.366 (4)	C12—C13	1.379 (4)
C2—C3	1.384 (4)	C13—C14	1.374 (4)
C3—C4	1.378 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.373 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.369 (5)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.382 (4)	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600

C1—N1—N2	118.8 (3)	C10—C9—C14	115.6 (4)
C1—N1—H1	120.6	C10—C9—C8	123.6 (4)
N2—N1—H1	120.6	C14—C9—C8	120.8 (4)
C8—N2—N1	114.7 (3)	C11—C10—C9	123.0 (4)
C12—N3—C16	120.3 (4)	C11—C10—H10	118.5
C12—N3—C15	119.2 (4)	C9—C10—H10	118.5
C16—N3—C15	116.9 (4)	C10—C11—C12	121.5 (4)
O1—C1—N1	123.7 (3)	C10—C11—H11	119.2
O1—C1—C2	121.1 (4)	C12—C11—H11	119.2
N1—C1—C2	115.2 (3)	C11—C12—C13	115.9 (4)
C7—C2—C3	119.2 (3)	C11—C12—N3	121.5 (4)
C7—C2—C1	118.2 (4)	C13—C12—N3	122.5 (4)
C3—C2—C1	122.6 (4)	C14—C13—C12	121.3 (4)
C4—C3—C2	120.3 (4)	C14—C13—H13	119.4
C4—C3—H3	119.9	C12—C13—H13	119.4
C2—C3—H3	119.9	C9—C14—C13	122.6 (4)
C5—C4—C3	120.0 (4)	C9—C14—H14	118.7
C5—C4—H4	120.0	C13—C14—H14	118.7
C3—C4—H4	120.0	N3—C15—H15A	109.5
C6—C5—C4	120.0 (4)	N3—C15—H15B	109.5
C6—C5—H5	120.0	H15A—C15—H15B	109.5
C4—C5—H5	120.0	N3—C15—H15C	109.5
C5—C6—C7	120.0 (4)	H15A—C15—H15C	109.5
C5—C6—H6	120.0	H15B—C15—H15C	109.5
C7—C6—H6	120.0	N3—C16—H16A	109.5
C2—C7—C6	120.6 (4)	N3—C16—H16B	109.5
C2—C7—H7	119.7	H16A—C16—H16B	109.5
C6—C7—H7	119.7	N3—C16—H16C	109.5
N2—C8—C9	121.0 (4)	H16A—C16—H16C	109.5
N2—C8—H8	119.5	H16B—C16—H16C	109.5
C9—C8—H8	119.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.19	2.982 (4)	153

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O
M_r	267.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	5.131 (3), 8.446 (4), 32.502 (16)
V (Å³)	1408.5 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.31 × 0.15

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	6499, 1489, 768
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.066, 1.00
No. of reflections	1489
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.19	2.982 (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

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