N′-(1-Phenyl­ethyl­idene)isonicotinohydrazide

Jiang, J.; Chen, J.; Yang, J.; Jian, F.-F.

doi:10.1107/S1600536809048569

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3125

doi:10.1107/S1600536809048569

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N′-(1-Phenylethylidene)isonicotinohydrazide

Jin-he Jiang,^a Jing Chen,^b Jie Yang ^a and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China, and ^bEast China University of Science and Technology, School of Chemical Engineering, Shanghai 200237, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 12 November 2009; accepted 16 November 2009; online 21 November 2009)

The title compound, C₁₄H₁₃N₃O, was prepared from hypnone and isoniazid. The dihedral angle between the aromatic rings is 12.21 (2)°. In the crystal, N—H⋯O hydrogen bonds link the molecules into chains propagating in [001] and C—H⋯O interactions consolidate the packing.

Related literature

For background on Schiff bases, see: Cimerman et al. (1997 ). For a related structure, see: Chen et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₃N₃O
M_r = 239.27
Monoclinic, P 2₁ /c
a = 25.878 (5) Å
b = 5.7100 (11) Å
c = 8.3089 (17) Å
β = 90.94 (3)°
V = 1227.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.25 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
11394 measured reflections
2821 independent reflections
2024 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.205
S = 1.03
2821 reflections
167 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1ⁱ	0.87 (2)	2.04 (3)	2.914 (2)	177 (2)
C4—H4A⋯O1ⁱ	0.93	2.43	3.123 (3)	131
C7—H7A⋯O1ⁱ	0.96	2.31	3.095 (3)	138
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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 global, I. DOI: 10.1107/S1600536809048569/hb5224sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048569/hb5224Isup2.hkl

checkCIF report

Comment top

Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound(I) and report its crystal structure herein.

In the title compound (I) (Fig. 1), the C8=N2 bond, 1.285 (3) Å, and the C6—N3 bond, 1.351 (3) Å, are both longer than those in a related compound (Chen et al., 2006). All other bond lengths are within normal ranges. The dihedral angle between the benzene and pyridine rings is 12.21 (2)°. The structure of (I) is stabilized by C—H···O,N—H···O and C—H···N hydrogen bonds (Table 1).

Related literature top

For background on Schiff bases, see: Cimerman et al. (1997). For a related structure, see: Chen et al. (2006).

Experimental top

A mixture of the isoniazid (0.05 mol) and hypnone (0.05 mol) was stirred in refluxing ethanol(30 ml) for 2 h to afford the title compound (yield 78%). Colourless bars of (I) were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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) with displacement ellipsoids drawn at the 30% probability level.

N'-(1-Phenylethylidene)isonicotinohydrazide top

Crystal data top

C₁₄H₁₃N₃O	F(000) = 504
M_r = 239.27	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2024 reflections
a = 25.878 (5) Å	θ = 3.2–27.5°
b = 5.7100 (11) Å	µ = 0.09 mm⁻¹
c = 8.3089 (17) Å	T = 293 K
β = 90.94 (3)°	Bar, colourless
V = 1227.6 (4) Å³	0.35 × 0.25 × 0.25 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2024 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −33→33
11394 measured reflections	k = −7→7
2821 independent reflections	l = −9→10

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.205	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.1014P)² + 0.6215P] where P = (F_o² + 2F_c²)/3
2821 reflections	(Δ/σ)_max < 0.001
167 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₄H₁₃N₃O	V = 1227.6 (4) Å³
M_r = 239.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 25.878 (5) Å	µ = 0.09 mm⁻¹
b = 5.7100 (11) Å	T = 293 K
c = 8.3089 (17) Å	0.35 × 0.25 × 0.25 mm
β = 90.94 (3)°

Data collection top

Bruker SMART CCD diffractometer	2024 reflections with I > 2σ(I)
11394 measured reflections	R_int = 0.046
2821 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.205	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.24 e Å⁻³
2821 reflections	Δρ_min = −0.29 e Å⁻³
167 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
N3	0.28050 (6)	0.2893 (3)	0.9742 (2)	0.0401 (4)
N2	0.23151 (7)	0.3104 (3)	1.0394 (2)	0.0414 (5)
C6	0.31164 (7)	0.1224 (4)	1.0382 (2)	0.0366 (5)
O1	0.30052 (6)	0.0099 (3)	1.15887 (18)	0.0472 (4)
C9	0.15153 (7)	0.4982 (4)	1.0663 (2)	0.0364 (5)
C8	0.20515 (8)	0.4938 (4)	1.0019 (2)	0.0356 (5)
C3	0.36258 (7)	0.0813 (4)	0.9583 (2)	0.0375 (5)
C4	0.38721 (8)	0.2432 (4)	0.8623 (3)	0.0446 (5)
H4A	0.3719	0.3870	0.8390	0.054*
C7	0.22348 (9)	0.6943 (4)	0.9029 (3)	0.0492 (6)
H7A	0.2583	0.6658	0.8704	0.074*
H7B	0.2223	0.8356	0.9654	0.074*
H7C	0.2016	0.7107	0.8092	0.074*
C10	0.13477 (8)	0.3243 (4)	1.1704 (3)	0.0476 (6)
H10A	0.1574	0.2058	1.2021	0.057*
C13	0.06659 (9)	0.6712 (5)	1.0781 (3)	0.0591 (7)
H13A	0.0437	0.7887	1.0468	0.071*
C11	0.08489 (9)	0.3254 (5)	1.2275 (3)	0.0564 (7)
H11A	0.0744	0.2092	1.2982	0.068*
C14	0.11683 (9)	0.6724 (5)	1.0213 (3)	0.0501 (6)
H14A	0.1273	0.7911	0.9524	0.060*
C2	0.38778 (9)	−0.1288 (5)	0.9907 (3)	0.0526 (6)
H2B	0.3728	−0.2414	1.0561	0.063*
N1	0.45942 (8)	−0.0143 (5)	0.8287 (3)	0.0630 (7)
C12	0.05063 (8)	0.4978 (5)	1.1801 (3)	0.0558 (7)
H12A	0.0169	0.4965	1.2170	0.067*
C5	0.43514 (9)	0.1864 (5)	0.8015 (3)	0.0564 (7)
H5A	0.4514	0.2966	0.7373	0.068*
C1	0.43566 (10)	−0.1669 (5)	0.9235 (4)	0.0658 (8)
H1B	0.4523	−0.3078	0.9460	0.079*
H3A	0.2875 (9)	0.349 (5)	0.881 (3)	0.045 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N3	0.0333 (9)	0.0442 (10)	0.0431 (9)	0.0044 (7)	0.0129 (7)	0.0055 (8)
N2	0.0334 (9)	0.0454 (11)	0.0459 (9)	0.0043 (7)	0.0134 (7)	0.0031 (8)
C6	0.0323 (9)	0.0408 (11)	0.0368 (9)	−0.0011 (8)	0.0055 (8)	−0.0025 (8)
O1	0.0431 (8)	0.0558 (11)	0.0431 (8)	0.0037 (7)	0.0106 (7)	0.0078 (7)
C9	0.0321 (9)	0.0400 (11)	0.0372 (10)	0.0010 (8)	0.0026 (8)	−0.0047 (8)
C8	0.0348 (10)	0.0366 (11)	0.0355 (9)	0.0004 (8)	0.0044 (8)	−0.0050 (8)
C3	0.0308 (9)	0.0431 (12)	0.0387 (10)	−0.0001 (8)	0.0042 (8)	−0.0065 (9)
C4	0.0328 (10)	0.0499 (13)	0.0513 (12)	−0.0003 (9)	0.0073 (9)	0.0020 (10)
C7	0.0497 (13)	0.0392 (13)	0.0590 (13)	0.0002 (9)	0.0154 (11)	0.0030 (10)
C10	0.0359 (11)	0.0496 (14)	0.0573 (13)	0.0044 (9)	0.0049 (10)	0.0088 (11)
C13	0.0416 (12)	0.0639 (18)	0.0720 (17)	0.0195 (11)	0.0061 (12)	0.0028 (13)
C11	0.0399 (12)	0.0642 (17)	0.0654 (15)	−0.0024 (11)	0.0128 (11)	0.0112 (13)
C14	0.0454 (12)	0.0478 (14)	0.0572 (13)	0.0081 (10)	0.0071 (11)	0.0061 (11)
C2	0.0435 (12)	0.0449 (14)	0.0697 (15)	0.0046 (10)	0.0102 (11)	0.0025 (12)
N1	0.0366 (10)	0.0716 (17)	0.0813 (16)	0.0040 (10)	0.0147 (10)	−0.0137 (13)
C12	0.0310 (10)	0.0702 (19)	0.0662 (15)	0.0045 (10)	0.0087 (10)	−0.0048 (13)
C5	0.0349 (11)	0.0729 (19)	0.0619 (14)	−0.0045 (11)	0.0135 (10)	0.0007 (13)
C1	0.0445 (13)	0.0534 (16)	0.100 (2)	0.0129 (11)	0.0110 (14)	−0.0080 (15)

Geometric parameters (Å, º) top

N3—C6	1.351 (3)	C7—H7C	0.9600
N3—N2	1.392 (2)	C10—C11	1.382 (3)
N3—H3A	0.87 (2)	C10—H10A	0.9300
N2—C8	1.285 (3)	C13—C12	1.371 (4)
C6—O1	1.229 (2)	C13—C14	1.391 (3)
C6—C3	1.504 (3)	C13—H13A	0.9300
C9—C14	1.387 (3)	C11—C12	1.378 (4)
C9—C10	1.391 (3)	C11—H11A	0.9300
C9—C8	1.496 (3)	C14—H14A	0.9300
C8—C7	1.492 (3)	C2—C1	1.385 (3)
C3—C4	1.384 (3)	C2—H2B	0.9300
C3—C2	1.390 (3)	N1—C5	1.324 (4)
C4—C5	1.385 (3)	N1—C1	1.332 (4)
C4—H4A	0.9300	C12—H12A	0.9300
C7—H7A	0.9600	C5—H5A	0.9300
C7—H7B	0.9600	C1—H1B	0.9300

C6—N3—N2	116.69 (17)	C11—C10—C9	120.8 (2)
C6—N3—H3A	119.8 (16)	C11—C10—H10A	119.6
N2—N3—H3A	121.1 (16)	C9—C10—H10A	119.6
C8—N2—N3	117.33 (18)	C12—C13—C14	120.4 (2)
O1—C6—N3	122.91 (18)	C12—C13—H13A	119.8
O1—C6—C3	119.80 (19)	C14—C13—H13A	119.8
N3—C6—C3	117.27 (18)	C12—C11—C10	120.4 (2)
C14—C9—C10	118.20 (19)	C12—C11—H11A	119.8
C14—C9—C8	121.05 (19)	C10—C11—H11A	119.8
C10—C9—C8	120.74 (18)	C9—C14—C13	120.6 (2)
N2—C8—C7	125.95 (18)	C9—C14—H14A	119.7
N2—C8—C9	114.75 (18)	C13—C14—H14A	119.7
C7—C8—C9	119.30 (18)	C1—C2—C3	118.5 (2)
C4—C3—C2	117.99 (19)	C1—C2—H2B	120.7
C4—C3—C6	124.4 (2)	C3—C2—H2B	120.7
C2—C3—C6	117.5 (2)	C5—N1—C1	116.4 (2)
C3—C4—C5	118.5 (2)	C13—C12—C11	119.6 (2)
C3—C4—H4A	120.8	C13—C12—H12A	120.2
C5—C4—H4A	120.8	C11—C12—H12A	120.2
C8—C7—H7A	109.5	N1—C5—C4	124.5 (2)
C8—C7—H7B	109.5	N1—C5—H5A	117.8
H7A—C7—H7B	109.5	C4—C5—H5A	117.8
C8—C7—H7C	109.5	N1—C1—C2	124.1 (3)
H7A—C7—H7C	109.5	N1—C1—H1B	117.9
H7B—C7—H7C	109.5	C2—C1—H1B	117.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1ⁱ	0.87 (2)	2.04 (3)	2.914 (2)	177 (2)
C4—H4A···O1ⁱ	0.93	2.43	3.123 (3)	131
C7—H7A···O1ⁱ	0.96	2.31	3.095 (3)	138

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₃O
M_r	239.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	25.878 (5), 5.7100 (11), 8.3089 (17)
β (°)	90.94 (3)
V (Å³)	1227.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11394, 2821, 2024
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.205, 1.03
No. of reflections	2821
No. of parameters	167
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.29

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
N3—H3A···O1ⁱ	0.87 (2)	2.04 (3)	2.914 (2)	177 (2)
C4—H4A···O1ⁱ	0.93	2.43	3.123 (3)	131
C7—H7A···O1ⁱ	0.96	2.31	3.095 (3)	138

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The authors would like to thank the National Natural Science Foundation of Shandong Province (Y2008B29) and the Yuandu Scholar Fund of Weifang City for support.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, S.-S., Zhang, S.-P., Huang, C.-B. & Shao, S.-C. (2006). Acta Cryst. E62, o31–o32. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar