N′-[(E)-3-Pyridylmethyl­idene]benzo­hydrazide

Wen, L.; Yin, H.; Li, W.; Li, K.

doi:10.1107/S160053680903894X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2623

https://doi.org/10.1107/S160053680903894X

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N′-[(E)-3-Pyridylmethylidene]benzohydrazide

Liyuan Wen,^a Handong Yin,^a ^* Wenkuan Li ^a and Kang Li ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 22 September 2009; accepted 25 September 2009; online 3 October 2009)

The title compound, C₁₃H₁₁N₃O, was prepared by the reaction of benzohydrazide and nicotinaldehyde. The dihedral angle between the planes of the two aromatic rings is 47.78 (9)°. The crystal structure is stabilized by intermolecular N—H⋯N hydrogen-bonding interactions.

Related literature

For related structures, see: Yin et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₁N₃O
M_r = 225.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.6193 (13) Å
b = 10.6291 (17) Å
c = 13.530 (2) Å
V = 1095.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.21 × 0.18 × 0.08 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.981, T_max = 0.993
5473 measured reflections
1136 independent reflections
612 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.104
S = 1.18
1136 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3ⁱ	0.86	2.40	3.236 (5)	164
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S160053680903894X/gk2228sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680903894X/gk2228Isup2.hkl

checkCIF report

Comment top

Acylhydrazones, as an example of Schiff bases, and their metal complexes have been widely studied due to their versatile applications in the fields of analytical and medicinal chemistry and biotechnology. These ligands, owing to their facile keto-enol tautomerization and the availability of several potential donor sites, can coordinate with metals (Yin et al., 2008). We report here the synthesis and structure of the title compound. The molecular structure of the title compound is shown in Fig. 1. The hydrazone molecule crystallizes as an E isomer. In the crystal structure, there exist intermolecular N—H···N hydrogen bonds (Table 1). As seen in Fig. 2, the molecules are linked into one-dimensional extended chain structure.

Related literature top

For related structures, see: Yin et al. (2008).

Experimental top

A mixture of benzohydrazide (10 mmol) and nicotinaldehyde (10 mmol) was refluxed in ethanol (40 ml) for 2 h at 353K. After the solution had cooled down to room temperature yellow sediment appeared. The product was crystallized from a solution of methanol to yield yellow block-shaped crystals of the title compound (yield 78%). Anal. Calcd (%) for C₁₃H₁₁N₃O (Mr = 225.25): C,69.32; H, 4.92; N, 18.65. Found (%): C, 69.21; H, 4.97; N, 18.76.

Structure description top

For related structures, see: Yin et al. (2008).

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 molecule of the title compound, shown with 50% probability displacement ellipsoids.
	Fig. 2. A view of the one-dimensional extended chain structure in the title compound.

N'-[(E)-3-Pyridylmethylidene]benzohydrazide top

Crystal data top

C₁₃H₁₁N₃O	F(000) = 472
M_r = 225.25	D_x = 1.365 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 764 reflections
a = 7.6193 (13) Å	θ = 2.4–25.1°
b = 10.6291 (17) Å	µ = 0.09 mm⁻¹
c = 13.530 (2) Å	T = 298 K
V = 1095.7 (3) Å³	Block, yellow
Z = 4	0.21 × 0.18 × 0.08 mm

Data collection top

Siemens SMART CCD diffractometer	1136 independent reflections
Radiation source: fine-focus sealed tube	612 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
φ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
T_min = 0.981, T_max = 0.993	k = −12→11
5473 measured reflections	l = −12→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0242P)² + 0.2399P] where P = (F_o² + 2F_c²)/3
1136 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₃H₁₁N₃O	V = 1095.7 (3) Å³
M_r = 225.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.6193 (13) Å	µ = 0.09 mm⁻¹
b = 10.6291 (17) Å	T = 298 K
c = 13.530 (2) Å	0.21 × 0.18 × 0.08 mm

Data collection top

Siemens SMART CCD diffractometer	1136 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	612 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.993	R_int = 0.073
5473 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.18	Δρ_max = 0.20 e Å⁻³
1136 reflections	Δρ_min = −0.20 e Å⁻³
154 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.1276 (5)	0.7488 (3)	0.4106 (3)	0.0430 (12)
H1	0.1551	0.8129	0.3750	0.052*
N2	0.1085 (5)	0.7596 (4)	0.5111 (3)	0.0410 (11)
N3	0.1881 (5)	1.0185 (4)	0.7966 (3)	0.0450 (12)
O1	0.0701 (5)	0.5389 (3)	0.4181 (2)	0.0544 (10)
C1	0.1015 (7)	0.6334 (4)	0.3688 (4)	0.0386 (13)
C2	0.1109 (6)	0.6291 (4)	0.2602 (3)	0.0327 (12)
C3	0.0535 (7)	0.7257 (4)	0.2001 (4)	0.0438 (14)
H3	0.0107	0.7992	0.2285	0.053*
C4	0.0588 (7)	0.7150 (5)	0.0986 (4)	0.0523 (15)
H4	0.0175	0.7805	0.0594	0.063*
C5	0.1247 (7)	0.6078 (5)	0.0548 (4)	0.0559 (17)
H5	0.1301	0.6013	−0.0137	0.067*
C6	0.1826 (7)	0.5105 (4)	0.1136 (4)	0.0515 (15)
H6	0.2268	0.4376	0.0848	0.062*
C7	0.1748 (6)	0.5212 (4)	0.2156 (4)	0.0448 (14)
H7	0.2132	0.4547	0.2547	0.054*
C8	0.1525 (6)	0.8640 (5)	0.5499 (3)	0.0446 (14)
H8	0.1941	0.9288	0.5101	0.054*
C9	0.1968 (6)	0.9926 (4)	0.6998 (3)	0.0432 (14)
H9	0.2460	1.0533	0.6588	0.052*
C10	0.1383 (6)	0.8825 (4)	0.6558 (4)	0.0365 (13)
C11	0.0676 (6)	0.7933 (4)	0.7186 (4)	0.0416 (14)
H11	0.0272	0.7173	0.6933	0.050*
C12	0.0567 (7)	0.8168 (5)	0.8183 (4)	0.0492 (15)
H12	0.0094	0.7572	0.8610	0.059*
C13	0.1173 (6)	0.9306 (5)	0.8537 (4)	0.0497 (15)
H13	0.1080	0.9465	0.9211	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.066 (3)	0.036 (2)	0.026 (2)	−0.006 (2)	0.001 (2)	−0.0031 (19)
N2	0.051 (3)	0.039 (2)	0.033 (3)	−0.002 (2)	0.003 (2)	0.0001 (19)
N3	0.048 (3)	0.046 (2)	0.041 (3)	−0.003 (2)	0.001 (2)	−0.008 (2)
O1	0.080 (3)	0.0399 (19)	0.044 (2)	−0.009 (2)	−0.004 (2)	0.0059 (18)
C1	0.043 (3)	0.036 (3)	0.037 (3)	−0.005 (3)	−0.006 (3)	−0.003 (3)
C2	0.030 (3)	0.033 (3)	0.035 (3)	−0.004 (3)	0.002 (3)	−0.004 (2)
C3	0.057 (4)	0.033 (3)	0.042 (4)	0.004 (3)	0.005 (3)	−0.005 (3)
C4	0.063 (4)	0.054 (3)	0.040 (4)	−0.002 (3)	−0.007 (3)	0.003 (3)
C5	0.077 (4)	0.056 (4)	0.035 (3)	−0.002 (3)	0.002 (3)	−0.006 (3)
C6	0.063 (4)	0.037 (3)	0.055 (4)	0.004 (3)	0.005 (3)	−0.011 (3)
C7	0.050 (4)	0.036 (3)	0.049 (4)	−0.004 (3)	0.000 (3)	−0.001 (3)
C8	0.057 (4)	0.039 (3)	0.038 (3)	−0.003 (3)	0.001 (3)	0.003 (3)
C9	0.056 (4)	0.038 (3)	0.036 (3)	−0.002 (3)	0.002 (3)	0.000 (3)
C10	0.044 (3)	0.035 (3)	0.030 (3)	−0.002 (3)	0.000 (3)	0.002 (2)
C11	0.045 (4)	0.038 (3)	0.042 (4)	−0.002 (3)	0.000 (3)	−0.002 (3)
C12	0.060 (4)	0.048 (3)	0.039 (3)	−0.010 (3)	0.004 (3)	0.006 (3)
C13	0.052 (4)	0.061 (3)	0.037 (3)	−0.002 (3)	0.004 (3)	−0.006 (3)

Geometric parameters (Å, º) top

N1—C1	1.365 (5)	C5—H5	0.9300
N1—N2	1.372 (5)	C6—C7	1.386 (6)
N1—H1	0.8600	C6—H6	0.9300
N2—C8	1.273 (6)	C7—H7	0.9300
N3—C13	1.327 (6)	C8—C10	1.451 (6)
N3—C9	1.340 (5)	C8—H8	0.9300
O1—C1	1.229 (5)	C9—C10	1.386 (6)
C1—C2	1.473 (6)	C9—H9	0.9300
C2—C3	1.380 (6)	C10—C11	1.381 (6)
C2—C7	1.385 (6)	C11—C12	1.375 (6)
C3—C4	1.378 (6)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.381 (6)
C4—C5	1.379 (6)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.377 (6)

C1—N1—N2	118.1 (4)	C7—C6—H6	120.0
C1—N1—H1	121.0	C2—C7—C6	121.1 (5)
N2—N1—H1	121.0	C2—C7—H7	119.5
C8—N2—N1	117.0 (4)	C6—C7—H7	119.5
C13—N3—C9	116.4 (4)	N2—C8—C10	120.4 (5)
O1—C1—N1	122.5 (5)	N2—C8—H8	119.8
O1—C1—C2	121.7 (5)	C10—C8—H8	119.8
N1—C1—C2	115.7 (4)	N3—C9—C10	125.2 (4)
C3—C2—C7	118.1 (4)	N3—C9—H9	117.4
C3—C2—C1	123.4 (5)	C10—C9—H9	117.4
C7—C2—C1	118.5 (5)	C11—C10—C9	116.2 (4)
C4—C3—C2	121.1 (5)	C11—C10—C8	122.9 (5)
C4—C3—H3	119.5	C9—C10—C8	120.9 (5)
C2—C3—H3	119.5	C12—C11—C10	120.1 (5)
C3—C4—C5	120.5 (5)	C12—C11—H11	119.9
C3—C4—H4	119.8	C10—C11—H11	119.9
C5—C4—H4	119.8	C11—C12—C13	118.6 (5)
C6—C5—C4	119.2 (5)	C11—C12—H12	120.7
C6—C5—H5	120.4	C13—C12—H12	120.7
C4—C5—H5	120.4	N3—C13—C12	123.4 (5)
C5—C6—C7	120.0 (5)	N3—C13—H13	118.3
C5—C6—H6	120.0	C12—C13—H13	118.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3ⁱ	0.86	2.40	3.236 (5)	164

Symmetry code: (i) −x+1/2, −y+2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁N₃O
M_r	225.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.6193 (13), 10.6291 (17), 13.530 (2)
V (Å³)	1095.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.21 × 0.18 × 0.08

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.981, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5473, 1136, 612
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.104, 1.18
No. of reflections	1136
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

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···N3ⁱ	0.86	2.40	3.236 (5)	164

Symmetry code: (i) −x+1/2, −y+2, z−1/2.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (20771053), the Natural Science Foundation of Shandong Province (Y2008B48) and the Students Technology Cultural Innovation Fund of Liaocheng University (SRT08044HX2) for financial support.

References

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Yin, H., Cui, J. & Qiao, Y. (2008). Polyhedron, 27, 2157–2166. Web of Science CSD CrossRef CAS Google Scholar