4-Dimethyl-amino-N'-(3-pyridyl-methyl-idene)benzohydrazide.

The title compound, C(15)H(16)N(4)O, was prepared by the reaction of pyridine-3-carbaldehyde with 4-dimethyl-amino-benzo-hydrazide in methanol. The dihedral angle between the pyridine and the benzene rings is 5.1 (3)°. In the crystal structure, the hydrazone mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For the synthesis and biological applications of hydrazone compounds, see: Alvarez et al. (2008 ▶); Angelusiu et al. (2010 ▶); Ajani et al. (2010 ▶); El-Dissouky et al. (2010 ▶); Avaji et al. (2009 ▶); Fouda et al. (2008 ▶). For the crystal structures of similar hydrazone compounds, see: Wen et al. (2009 ▶); Fun et al. (2008 ▶); Ji & Lu (2010 ▶); Ahmad et al. (2010 ▶); Cui et al. (2009 ▶).

Experimental

Crystal data

C15H16N4O

M = 268.32

Orthorhombic,

a = 11.513 (2) Å

b = 7.898 (2) Å

c = 30.359 (3) Å

V = 2760.5 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.10 × 0.07 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.992, T max = 0.996

20776 measured reflections

2991 independent reflections

1163 reflections with I > 2σ(I)

R int = 0.190

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.151

S = 0.79

2991 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810037670/rz2491sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037670/rz2491Isup2.hkl

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

C15H16N4O	F(000) = 1136
Mr = 268.32	Dx = 1.291 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1003 reflections
a = 11.513 (2) Å	θ = 2.3–24.0°
b = 7.898 (2) Å	µ = 0.09 mm−1
c = 30.359 (3) Å	T = 298 K
V = 2760.5 (9) Å3	Block, colourless
Z = 8	0.10 × 0.07 × 0.05 mm

Bruker SMART CCD area-detector diffractometer	2991 independent reflections
Radiation source: fine-focus sealed tube	1163 reflections with I > 2σ(I)
graphite	Rint = 0.190
ω scans	θmax = 27.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→14
Tmin = 0.992, Tmax = 0.996	k = −10→9
20776 measured reflections	l = −38→37

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 0.79	w = 1/[σ2(Fo2) + (0.0518P)2] where P = (Fo2 + 2Fc2)/3
2991 reflections	(Δ/σ)max < 0.001
186 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.25 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
N1	0.7015 (2)	0.4212 (3)	0.79621 (8)	0.0715 (8)
N2	0.74617 (19)	0.2877 (3)	0.66360 (7)	0.0442 (6)
N3	0.7654 (2)	0.2199 (3)	0.62206 (7)	0.0462 (6)
N4	0.8832 (2)	0.0665 (3)	0.41884 (7)	0.0548 (7)
O1	0.89752 (16)	0.4234 (2)	0.60695 (5)	0.0494 (5)
C1	0.6436 (2)	0.2668 (4)	0.73145 (8)	0.0425 (7)
C2	0.5449 (3)	0.2126 (4)	0.75284 (10)	0.0636 (9)
H2	0.4923	0.1416	0.7387	0.076*
C3	0.5253 (3)	0.2652 (4)	0.79551 (10)	0.0677 (10)
H3A	0.4595	0.2296	0.8107	0.081*
C4	0.6033 (3)	0.3691 (4)	0.81491 (10)	0.0664 (10)
H4	0.5871	0.4069	0.8433	0.080*
C5	0.7181 (3)	0.3692 (4)	0.75487 (9)	0.0581 (9)
H5	0.7854	0.4050	0.7407	0.070*
C6	0.6688 (2)	0.2116 (4)	0.68628 (9)	0.0459 (8)
H6	0.6283	0.1210	0.6742	0.055*
C7	0.8431 (2)	0.2965 (4)	0.59507 (9)	0.0405 (7)
C8	0.8553 (2)	0.2255 (3)	0.55060 (8)	0.0374 (7)
C9	0.7769 (2)	0.1128 (3)	0.53203 (8)	0.0416 (7)
H9	0.7157	0.0732	0.5491	0.050*
C10	0.7866 (2)	0.0575 (3)	0.48906 (8)	0.0456 (7)
H10	0.7325	−0.0185	0.4778	0.055*
C11	0.8776 (2)	0.1154 (3)	0.46229 (9)	0.0423 (7)
C12	0.9577 (2)	0.2268 (4)	0.48112 (9)	0.0506 (8)
H12	1.0198	0.2656	0.4643	0.061*
C13	0.9464 (2)	0.2797 (3)	0.52384 (9)	0.0470 (8)
H13	1.0012	0.3540	0.5354	0.056*
C14	0.8071 (3)	−0.0613 (4)	0.40150 (9)	0.0736 (10)
H14A	0.8202	−0.1660	0.4168	0.110*
H14B	0.8225	−0.0765	0.3707	0.110*
H14C	0.7279	−0.0266	0.4055	0.110*
C15	0.9728 (3)	0.1326 (4)	0.38994 (9)	0.0780 (11)
H15A	0.9755	0.2537	0.3924	0.117*
H15B	0.9556	0.1018	0.3601	0.117*
H15C	1.0467	0.0859	0.3982	0.117*
H3	0.728 (2)	0.124 (2)	0.6156 (9)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.084 (2)	0.094 (2)	0.0365 (16)	−0.0072 (18)	0.0065 (15)	−0.0122 (15)
N2	0.0460 (15)	0.0567 (17)	0.0298 (13)	0.0026 (13)	0.0005 (11)	−0.0049 (12)
N3	0.0557 (17)	0.0556 (18)	0.0274 (12)	−0.0044 (13)	0.0040 (11)	−0.0085 (12)
N4	0.0619 (17)	0.0693 (18)	0.0331 (14)	−0.0091 (15)	0.0156 (13)	−0.0065 (13)
O1	0.0555 (13)	0.0565 (13)	0.0363 (12)	−0.0069 (11)	−0.0072 (9)	−0.0053 (10)
C1	0.0428 (17)	0.0533 (19)	0.0313 (16)	0.0044 (15)	0.0021 (13)	0.0008 (14)
C2	0.050 (2)	0.087 (3)	0.054 (2)	−0.0078 (18)	0.0038 (16)	−0.0122 (18)
C3	0.058 (2)	0.103 (3)	0.042 (2)	0.004 (2)	0.0161 (17)	−0.0005 (19)
C4	0.078 (3)	0.088 (3)	0.0328 (18)	0.018 (2)	0.0087 (19)	−0.0037 (18)
C5	0.062 (2)	0.076 (2)	0.0366 (18)	−0.0078 (18)	0.0079 (16)	−0.0041 (16)
C6	0.0441 (18)	0.055 (2)	0.0382 (17)	0.0024 (15)	−0.0041 (14)	−0.0068 (15)
C7	0.0432 (18)	0.0435 (19)	0.0348 (17)	0.0083 (15)	−0.0065 (14)	0.0014 (15)
C8	0.0382 (16)	0.0434 (18)	0.0305 (16)	0.0019 (14)	−0.0009 (12)	0.0024 (13)
C9	0.0453 (18)	0.0491 (19)	0.0304 (15)	−0.0046 (15)	0.0082 (13)	0.0051 (13)
C10	0.0497 (18)	0.053 (2)	0.0340 (16)	−0.0088 (15)	0.0014 (14)	−0.0004 (14)
C11	0.0454 (18)	0.0516 (19)	0.0301 (16)	0.0027 (15)	0.0065 (14)	0.0013 (14)
C12	0.0433 (18)	0.064 (2)	0.0445 (18)	−0.0057 (16)	0.0133 (14)	−0.0009 (16)
C13	0.0407 (18)	0.057 (2)	0.0431 (18)	−0.0047 (15)	−0.0024 (14)	−0.0050 (15)
C14	0.102 (3)	0.087 (3)	0.0322 (18)	−0.014 (2)	0.0041 (18)	−0.0140 (17)
C15	0.088 (3)	0.098 (3)	0.047 (2)	−0.010 (2)	0.0301 (19)	−0.0022 (18)

N1—C4	1.331 (4)	C6—H6	0.9300
N1—C5	1.334 (3)	C7—C8	1.469 (3)
N2—C6	1.276 (3)	C8—C9	1.388 (3)
N2—N3	1.388 (3)	C8—C13	1.394 (3)
N3—C7	1.356 (3)	C9—C10	1.380 (3)
N3—H3	0.894 (10)	C9—H9	0.9300
N4—C11	1.376 (3)	C10—C11	1.402 (3)
N4—C14	1.436 (3)	C10—H10	0.9300
N4—C15	1.451 (3)	C11—C12	1.397 (3)
O1—C7	1.236 (3)	C12—C13	1.369 (3)
C1—C2	1.377 (4)	C12—H12	0.9300
C1—C5	1.377 (4)	C13—H13	0.9300
C1—C6	1.468 (3)	C14—H14A	0.9600
C2—C3	1.379 (4)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.352 (4)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—H5	0.9300
C4—N1—C5	115.3 (3)	C9—C8—C7	123.8 (2)
C6—N2—N3	114.8 (2)	C13—C8—C7	119.4 (3)
C7—N3—N2	118.8 (2)	C10—C9—C8	122.3 (2)
C7—N3—H3	124.4 (19)	C10—C9—H9	118.8
N2—N3—H3	116.7 (19)	C8—C9—H9	118.8
C11—N4—C14	121.3 (2)	C9—C10—C11	120.3 (3)
C11—N4—C15	120.8 (3)	C9—C10—H10	119.8
C14—N4—C15	117.7 (2)	C11—C10—H10	119.8
C2—C1—C5	116.9 (3)	N4—C11—C12	122.5 (2)
C2—C1—C6	120.8 (3)	N4—C11—C10	119.9 (3)
C5—C1—C6	122.3 (3)	C12—C11—C10	117.5 (2)
C1—C2—C3	119.0 (3)	C13—C12—C11	121.2 (2)
C1—C2—H2	120.5	C13—C12—H12	119.4
C3—C2—H2	120.5	C11—C12—H12	119.4
C4—C3—C2	118.9 (3)	C12—C13—C8	122.0 (3)
C4—C3—H3A	120.6	C12—C13—H13	119.0
C2—C3—H3A	120.6	C8—C13—H13	119.0
N1—C4—C3	124.5 (3)	N4—C14—H14A	109.5
N1—C4—H4	117.8	N4—C14—H14B	109.5
C3—C4—H4	117.8	H14A—C14—H14B	109.5
N1—C5—C1	125.3 (3)	N4—C14—H14C	109.5
N1—C5—H5	117.4	H14A—C14—H14C	109.5
C1—C5—H5	117.4	H14B—C14—H14C	109.5
N2—C6—C1	120.1 (3)	N4—C15—H15A	109.5
N2—C6—H6	119.9	N4—C15—H15B	109.5
C1—C6—H6	119.9	H15A—C15—H15B	109.5
O1—C7—N3	121.4 (3)	N4—C15—H15C	109.5
O1—C7—C8	122.0 (3)	H15A—C15—H15C	109.5
N3—C7—C8	116.6 (3)	H15B—C15—H15C	109.5
C9—C8—C13	116.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.89 (1)	2.16 (1)	3.035 (3)	166 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.89 (1)	2.16 (1)	3.035 (3)	166 (3)

Symmetry code: (i) .