N'-[(E)-3-Pyridylmethyl-idene]benzo-hydrazide.

The title compound, C(13)H(11)N(3)O, 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 inter-molecular N-H⋯N hydrogen-bonding inter-actions.

Related literature

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

Experimental

Crystal data

C13H11N3O

M = 225.25

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.104

S = 1.18

1136 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903894X/gk2228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903894X/gk2228Isup2.hkl

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

C13H11N3O	F(000) = 472
Mr = 225.25	Dx = 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

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

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(Fo2) + (0.0242P)2 + 0.2399P] where P = (Fo2 + 2Fc2)/3
1136 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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

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

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) .