N'-(1-Phenyl-ethyl-idene)isonicotinohydrazide.

The title compound, C(14)H(13)N(3)O, 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 mol-ecules into chains propagating in [001] and C-H⋯O inter-actions 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 = 239.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.205

S = 1.03

2821 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048569/hb5224sup1.cif

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

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

C14H13N3O	F(000) = 504
Mr = 239.27	Dx = 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

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

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(Fo2) + (0.1014P)2 + 0.6215P] where P = (Fo2 + 2Fc2)/3
2821 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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

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

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) .