2-Methyl-N'-[1-(2-pyrid-yl)ethyl-idene]benzohydrazide.

In the title compound, C(15)H(15)N(3)O, the dihedral angle between the pyridine and benzene rings is 36.3 (2)°. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ▶); Pyta et al. (2010 ▶); Angelusiu et al. (2010 ▶). For related structures, see: Fun et al. (2008 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶); Tang (2010 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H15N3O

M = 253.30

Orthorhombic,

a = 19.296 (3) Å

b = 8.1417 (18) Å

c = 17.294 (3) Å

V = 2716.8 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.986

13661 measured reflections

2966 independent reflections

1539 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.158

S = 1.02

2966 reflections

177 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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/S1600536810054267/sj5083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054267/sj5083Isup2.hkl

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

C15H15N3O	Dx = 1.239 Mg m−3
Mr = 253.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 1243 reflections
a = 19.296 (3) Å	θ = 2.5–24.6°
b = 8.1417 (18) Å	µ = 0.08 mm−1
c = 17.294 (3) Å	T = 298 K
V = 2716.8 (9) Å3	Block, colourless
Z = 8	0.20 × 0.20 × 0.18 mm
F(000) = 1072

Bruker SMART CCD area-detector diffractometer	2966 independent reflections
Radiation source: fine-focus sealed tube	1539 reflections with I > 2σ(I)
graphite	Rint = 0.069
ω scans	θmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
Tmin = 0.984, Tmax = 0.986	k = −10→10
13661 measured reflections	l = −13→22

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.5475P] where P = (Fo2 + 2Fc2)/3
2966 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N1	0.26051 (10)	0.9439 (2)	0.05651 (11)	0.0451 (5)
N2	0.28738 (9)	1.0589 (2)	0.00578 (11)	0.0450 (5)
N3	0.43437 (11)	1.1437 (2)	−0.10682 (12)	0.0623 (6)
O1	0.17755 (8)	1.12421 (19)	0.09416 (11)	0.0613 (5)
C1	0.16962 (11)	0.8519 (3)	0.14164 (13)	0.0423 (5)
C2	0.10054 (12)	0.8104 (3)	0.12641 (14)	0.0513 (6)
C3	0.07187 (15)	0.6857 (4)	0.17027 (18)	0.0751 (9)
H3	0.0266	0.6531	0.1602	0.090*
C4	0.10778 (18)	0.6085 (4)	0.22804 (19)	0.0832 (10)
H4	0.0866	0.5263	0.2569	0.100*
C5	0.17470 (16)	0.6520 (3)	0.24329 (16)	0.0689 (8)
H5	0.1990	0.6005	0.2829	0.083*
C6	0.20621 (13)	0.7725 (3)	0.19965 (14)	0.0536 (6)
H6	0.2521	0.8007	0.2092	0.064*
C7	0.05886 (13)	0.8927 (4)	0.06421 (16)	0.0682 (8)
H7A	0.0192	0.8263	0.0520	0.102*
H7B	0.0870	0.9060	0.0188	0.102*
H7C	0.0437	0.9984	0.0820	0.102*
C8	0.20235 (11)	0.9857 (3)	0.09561 (13)	0.0423 (5)
C9	0.34432 (13)	1.0263 (3)	−0.02897 (14)	0.0508 (6)
C10	0.36834 (13)	1.1545 (3)	−0.08374 (13)	0.0499 (6)
C11	0.32524 (14)	1.2794 (3)	−0.10794 (15)	0.0644 (7)
H11	0.2792	1.2825	−0.0921	0.077*
C12	0.35119 (18)	1.3991 (4)	−0.15583 (18)	0.0836 (10)
H12	0.3231	1.4851	−0.1723	0.100*
C13	0.41887 (19)	1.3901 (4)	−0.17897 (18)	0.0831 (10)
H13	0.4377	1.4695	−0.2114	0.100*
C14	0.45800 (16)	1.2616 (4)	−0.15322 (16)	0.0735 (9)
H14	0.5040	1.2561	−0.1690	0.088*
C15	0.38792 (17)	0.8767 (4)	−0.0182 (2)	0.1043 (13)
H15A	0.4022	0.8692	0.0349	0.156*
H15B	0.4281	0.8838	−0.0508	0.156*
H15C	0.3615	0.7810	−0.0317	0.156*
H1	0.2784 (13)	0.8410 (17)	0.0589 (16)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0503 (11)	0.0302 (10)	0.0547 (12)	0.0008 (9)	0.0072 (10)	0.0072 (10)
N2	0.0514 (11)	0.0343 (10)	0.0492 (12)	−0.0062 (9)	0.0018 (10)	0.0042 (9)
N3	0.0678 (14)	0.0579 (14)	0.0611 (14)	−0.0096 (11)	0.0209 (11)	−0.0052 (11)
O1	0.0568 (10)	0.0342 (9)	0.0930 (14)	0.0044 (8)	0.0086 (9)	0.0081 (9)
C1	0.0511 (14)	0.0319 (12)	0.0438 (13)	−0.0001 (10)	0.0069 (11)	−0.0016 (10)
C2	0.0489 (14)	0.0517 (15)	0.0533 (15)	−0.0068 (11)	0.0079 (12)	−0.0033 (12)
C3	0.0606 (17)	0.083 (2)	0.081 (2)	−0.0229 (16)	0.0119 (16)	0.0115 (18)
C4	0.090 (2)	0.078 (2)	0.082 (2)	−0.0174 (18)	0.0242 (19)	0.0276 (18)
C5	0.088 (2)	0.0617 (18)	0.0567 (17)	0.0042 (16)	0.0064 (15)	0.0158 (14)
C6	0.0614 (15)	0.0422 (14)	0.0573 (16)	0.0013 (12)	0.0007 (13)	0.0023 (12)
C7	0.0512 (15)	0.082 (2)	0.0719 (18)	−0.0008 (14)	−0.0049 (14)	0.0016 (16)
C8	0.0439 (13)	0.0300 (12)	0.0531 (14)	−0.0024 (10)	−0.0038 (11)	0.0020 (11)
C9	0.0557 (14)	0.0390 (14)	0.0576 (15)	0.0000 (11)	0.0078 (12)	0.0013 (12)
C10	0.0613 (16)	0.0434 (14)	0.0450 (14)	−0.0095 (12)	0.0070 (12)	−0.0049 (11)
C11	0.0624 (16)	0.0629 (17)	0.0678 (18)	−0.0059 (14)	−0.0004 (14)	0.0220 (15)
C12	0.092 (2)	0.081 (2)	0.078 (2)	−0.0112 (18)	−0.0011 (18)	0.0332 (18)
C13	0.105 (3)	0.081 (2)	0.0635 (19)	−0.032 (2)	0.0128 (18)	0.0146 (17)
C14	0.084 (2)	0.075 (2)	0.0621 (19)	−0.0227 (18)	0.0271 (16)	−0.0054 (17)
C15	0.090 (2)	0.076 (2)	0.147 (3)	0.0296 (18)	0.052 (2)	0.046 (2)

N1—C8	1.354 (3)	C6—H6	0.9300
N1—N2	1.384 (2)	C7—H7A	0.9600
N1—H1	0.907 (10)	C7—H7B	0.9600
N2—C9	1.280 (3)	C7—H7C	0.9600
N3—C14	1.332 (3)	C9—C10	1.484 (3)
N3—C10	1.338 (3)	C9—C15	1.492 (3)
O1—C8	1.225 (2)	C10—C11	1.379 (3)
C1—C6	1.386 (3)	C11—C12	1.374 (4)
C1—C2	1.400 (3)	C11—H11	0.9300
C1—C8	1.490 (3)	C12—C13	1.368 (4)
C2—C3	1.383 (3)	C12—H12	0.9300
C2—C7	1.501 (3)	C13—C14	1.365 (4)
C3—C4	1.369 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.365 (4)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.379 (3)	C15—H15C	0.9600
C5—H5	0.9300
C8—N1—N2	117.17 (17)	H7B—C7—H7C	109.5
C8—N1—H1	121.7 (17)	O1—C8—N1	123.0 (2)
N2—N1—H1	120.7 (18)	O1—C8—C1	121.2 (2)
C9—N2—N1	118.60 (19)	N1—C8—C1	115.71 (19)
C14—N3—C10	117.3 (2)	N2—C9—C10	114.9 (2)
C6—C1—C2	120.6 (2)	N2—C9—C15	126.5 (2)
C6—C1—C8	120.8 (2)	C10—C9—C15	118.5 (2)
C2—C1—C8	118.7 (2)	N3—C10—C11	122.2 (2)
C3—C2—C1	117.1 (2)	N3—C10—C9	116.2 (2)
C3—C2—C7	120.4 (2)	C11—C10—C9	121.6 (2)
C1—C2—C7	122.5 (2)	C12—C11—C10	119.1 (3)
C4—C3—C2	122.3 (3)	C12—C11—H11	120.4
C4—C3—H3	118.8	C10—C11—H11	120.4
C2—C3—H3	118.8	C13—C12—C11	119.1 (3)
C5—C4—C3	120.1 (3)	C13—C12—H12	120.4
C5—C4—H4	120.0	C11—C12—H12	120.4
C3—C4—H4	120.0	C14—C13—C12	118.3 (3)
C4—C5—C6	119.7 (3)	C14—C13—H13	120.9
C4—C5—H5	120.1	C12—C13—H13	120.9
C6—C5—H5	120.1	N3—C14—C13	124.0 (3)
C5—C6—C1	120.2 (2)	N3—C14—H14	118.0
C5—C6—H6	119.9	C13—C14—H14	118.0
C1—C6—H6	119.9	C9—C15—H15A	109.5
C2—C7—H7A	109.5	C9—C15—H15B	109.5
C2—C7—H7B	109.5	H15A—C15—H15B	109.5
H7A—C7—H7B	109.5	C9—C15—H15C	109.5
C2—C7—H7C	109.5	H15A—C15—H15C	109.5
H7A—C7—H7C	109.5	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.91 (1)	2.05 (1)	2.937 (2)	165 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.91 (1)	2.05 (1)	2.937 (2)	165 (3)

Symmetry code: (i) .