N'-(Di-2-pyridylmethyl-ene)benzo-hydrazide.

In the title Schiff base, C(18)H(14)N(4)O, the amido -NH- unit is connected to one of the two pyridyl N atoms at an N(-H)⋯N distance of 2.624 (2) Å. The mol-ecular packing features an inter-molecular C-H⋯N R(2) (2)(6) hydrogen-bonding ring motif.

Related literature

For medicinal applications of benzohydrazides, see: Raparti et al. (2009 ▶); Zhong et al. (2007 ▶). For a previous study on the synthesis of benzohyrazide derivatives, see: Abu-El-Halawa et al. (2007 ▶). For ring-motif analysis; see: Bernstein et al. (1995 ▶); Grell et al. (1999 ▶).

Experimental

Crystal data

C18H14N4O

M = 302.33

Monoclinic,

a = 8.2741 (5) Å

b = 22.1436 (14) Å

c = 8.8006 (5) Å

β = 108.974 (2)°

V = 1524.82 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.50 × 0.30 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007 ▶) T min = 0.968, T max = 0.989

33115 measured reflections

3491 independent reflections

2329 reflections with I > 2δ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.169

S = 0.99

3491 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶) and PLUTO (Motherwell et al., 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022090/ng2595sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022090/ng2595Isup2.hkl

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

C18H14N4O	F(000) = 632
Mr = 302.33	Dx = 1.317 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ybc	Cell parameters from 880 reflections
a = 8.2741 (5) Å	θ = 3.0–27.4°
b = 22.1436 (14) Å	µ = 0.09 mm−1
c = 8.8006 (5) Å	T = 295 K
β = 108.974 (2)°	Block, colourless
V = 1524.82 (15) Å3	0.50 × 0.30 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3491 independent reflections
Radiation source: fine-focus sealed tube	2329 reflections with I > 2δ(I)
graphite	Rint = 0.050
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007)	h = −10→10
Tmin = 0.968, Tmax = 0.989	k = −28→28
33115 measured reflections	l = −11→11

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1092P)2 + 0.076P] where P = (Fo2 + 2Fc2)/3
3491 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.24 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
O1	0.17708 (18)	0.55123 (6)	0.48480 (14)	0.0649 (4)
N1	0.21198 (18)	0.51374 (6)	0.73562 (16)	0.0485 (4)
H7	0.1902	0.5186	0.8240	0.058*
C1	0.1073 (2)	0.62760 (7)	0.8228 (2)	0.0513 (4)
H1	0.1787	0.6045	0.9058	0.062*
N2	0.29967 (18)	0.46379 (6)	0.71474 (16)	0.0472 (3)
C2	0.0312 (2)	0.67909 (8)	0.8581 (2)	0.0598 (5)
H2	0.0526	0.6907	0.9644	0.072*
N3	0.22378 (18)	0.47159 (6)	1.01763 (16)	0.0509 (4)
C3	−0.0768 (2)	0.71315 (8)	0.7347 (2)	0.0604 (5)
H3	−0.1280	0.7477	0.7583	0.072*
N4	0.4144 (2)	0.31839 (6)	0.84066 (19)	0.0550 (4)
C4	−0.1087 (2)	0.69618 (8)	0.5779 (2)	0.0590 (5)
H4	−0.1829	0.7189	0.4956	0.071*
C5	−0.0308 (2)	0.64538 (8)	0.5414 (2)	0.0524 (4)
H5	−0.0509	0.6346	0.4346	0.063*
C6	0.0777 (2)	0.61027 (7)	0.66396 (19)	0.0455 (4)
C7	0.1590 (2)	0.55591 (7)	0.61664 (19)	0.0485 (4)
C8	0.3333 (2)	0.42967 (7)	0.99547 (18)	0.0432 (4)
C9	0.4310 (2)	0.39466 (8)	1.1233 (2)	0.0527 (4)
H9	0.5048	0.3655	1.1072	0.063*
C10	0.4182 (3)	0.40325 (8)	1.2745 (2)	0.0572 (5)
H10	0.4845	0.3804	1.3609	0.069*
C11	0.3068 (2)	0.44583 (8)	1.2965 (2)	0.0533 (4)
H11	0.2958	0.4523	1.3971	0.064*
C12	0.2125 (2)	0.47854 (8)	1.1649 (2)	0.0551 (4)
H12	0.1363	0.5072	1.1789	0.066*
C13	0.3515 (2)	0.42534 (7)	0.83260 (18)	0.0433 (4)
C14	0.4492 (2)	0.37362 (7)	0.79543 (18)	0.0444 (4)
C15	0.5690 (2)	0.38299 (8)	0.71803 (19)	0.0514 (4)
H15	0.5880	0.4216	0.6856	0.062*
C16	0.6594 (2)	0.33445 (9)	0.6899 (2)	0.0611 (5)
H16	0.7415	0.3399	0.6399	0.073*
C17	0.6260 (3)	0.27757 (9)	0.7371 (2)	0.0645 (5)
H17	0.6853	0.2440	0.7199	0.077*
C18	0.5033 (3)	0.27192 (8)	0.8099 (2)	0.0617 (5)
H18	0.4802	0.2334	0.8399	0.074*

	U11	U22	U33	U12	U13	U23
O1	0.0939 (10)	0.0613 (8)	0.0480 (7)	0.0160 (7)	0.0345 (7)	0.0053 (6)
N1	0.0645 (9)	0.0402 (7)	0.0455 (8)	0.0074 (6)	0.0244 (7)	0.0017 (5)
C1	0.0561 (10)	0.0503 (9)	0.0458 (9)	0.0045 (7)	0.0141 (8)	0.0005 (7)
N2	0.0561 (8)	0.0404 (7)	0.0474 (8)	0.0030 (6)	0.0197 (6)	−0.0015 (6)
C2	0.0679 (12)	0.0604 (11)	0.0519 (10)	0.0054 (9)	0.0209 (9)	−0.0086 (8)
N3	0.0565 (9)	0.0531 (8)	0.0476 (8)	0.0065 (6)	0.0230 (6)	0.0016 (6)
C3	0.0657 (12)	0.0517 (10)	0.0663 (12)	0.0110 (8)	0.0251 (10)	−0.0015 (8)
N4	0.0674 (10)	0.0388 (7)	0.0649 (9)	−0.0004 (6)	0.0300 (8)	−0.0024 (6)
C4	0.0631 (11)	0.0563 (10)	0.0579 (11)	0.0115 (8)	0.0204 (9)	0.0128 (8)
C5	0.0606 (10)	0.0517 (9)	0.0463 (9)	0.0027 (8)	0.0192 (8)	0.0053 (7)
C6	0.0506 (9)	0.0430 (8)	0.0454 (9)	−0.0013 (7)	0.0192 (7)	0.0018 (6)
C7	0.0570 (10)	0.0464 (9)	0.0444 (9)	0.0018 (7)	0.0197 (7)	0.0023 (7)
C8	0.0476 (9)	0.0383 (8)	0.0456 (9)	−0.0028 (6)	0.0176 (7)	−0.0025 (6)
C9	0.0607 (10)	0.0493 (9)	0.0488 (9)	0.0084 (8)	0.0188 (8)	0.0000 (7)
C10	0.0720 (12)	0.0539 (10)	0.0439 (9)	0.0034 (8)	0.0165 (8)	0.0025 (7)
C11	0.0668 (11)	0.0527 (10)	0.0452 (9)	−0.0066 (8)	0.0249 (8)	−0.0041 (7)
C12	0.0623 (11)	0.0565 (10)	0.0538 (10)	0.0040 (8)	0.0289 (9)	−0.0021 (8)
C13	0.0477 (9)	0.0407 (8)	0.0427 (8)	−0.0021 (6)	0.0165 (7)	−0.0027 (6)
C14	0.0495 (9)	0.0417 (8)	0.0409 (8)	−0.0002 (6)	0.0132 (7)	−0.0025 (6)
C15	0.0564 (10)	0.0511 (9)	0.0487 (9)	−0.0005 (7)	0.0197 (8)	0.0007 (7)
C16	0.0597 (11)	0.0703 (12)	0.0584 (11)	0.0085 (9)	0.0264 (9)	−0.0030 (9)
C17	0.0699 (12)	0.0594 (11)	0.0622 (12)	0.0174 (9)	0.0189 (10)	−0.0082 (9)
C18	0.0770 (13)	0.0423 (9)	0.0672 (12)	0.0041 (8)	0.0255 (10)	−0.0031 (8)

O1—C7	1.2217 (18)	C6—C7	1.502 (2)
N1—C7	1.365 (2)	C8—C9	1.389 (2)
N1—N2	1.3677 (17)	C8—C13	1.492 (2)
N1—H7	0.8600	C9—C10	1.382 (2)
C1—C2	1.386 (2)	C9—H9	0.9300
C1—C6	1.392 (2)	C10—C11	1.375 (2)
C1—H1	0.9300	C10—H10	0.9300
N2—C13	1.302 (2)	C11—C12	1.374 (2)
C2—C3	1.384 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—H12	0.9300
N3—C12	1.338 (2)	C13—C14	1.498 (2)
N3—C8	1.355 (2)	C14—C15	1.389 (2)
C3—C4	1.371 (3)	C15—C16	1.377 (2)
C3—H3	0.9300	C15—H15	0.9300
N4—C18	1.343 (2)	C16—C17	1.382 (3)
N4—C14	1.3458 (19)	C16—H16	0.9300
C4—C5	1.385 (2)	C17—C18	1.371 (3)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.394 (2)	C18—H18	0.9300
C5—H5	0.9300
C7—N1—N2	120.17 (13)	C10—C9—C8	119.78 (15)
C7—N1—H7	119.9	C10—C9—H9	120.1
N2—N1—H7	119.9	C8—C9—H9	120.1
C2—C1—C6	120.52 (16)	C11—C10—C9	119.62 (16)
C2—C1—H1	119.7	C11—C10—H10	120.2
C6—C1—H1	119.7	C9—C10—H10	120.2
C13—N2—N1	118.27 (12)	C12—C11—C10	117.75 (15)
C3—C2—C1	119.78 (16)	C12—C11—H11	121.1
C3—C2—H2	120.1	C10—C11—H11	121.1
C1—C2—H2	120.1	N3—C12—C11	123.82 (16)
C12—N3—C8	118.61 (14)	N3—C12—H12	118.1
C4—C3—C2	120.29 (16)	C11—C12—H12	118.1
C4—C3—H3	119.9	N2—C13—C8	127.81 (14)
C2—C3—H3	119.9	N2—C13—C14	112.79 (13)
C18—N4—C14	116.92 (15)	C8—C13—C14	119.29 (13)
C3—C4—C5	120.30 (16)	N4—C14—C15	122.42 (15)
C3—C4—H4	119.8	N4—C14—C13	116.60 (14)
C5—C4—H4	119.8	C15—C14—C13	120.98 (14)
C4—C5—C6	120.28 (16)	C16—C15—C14	119.18 (16)
C4—C5—H5	119.9	C16—C15—H15	120.4
C6—C5—H5	119.9	C14—C15—H15	120.4
C1—C6—C5	118.80 (15)	C15—C16—C17	118.97 (17)
C1—C6—C7	123.43 (14)	C15—C16—H16	120.5
C5—C6—C7	117.76 (14)	C17—C16—H16	120.5
O1—C7—N1	124.24 (15)	C18—C17—C16	118.30 (17)
O1—C7—C6	122.38 (14)	C18—C17—H17	120.8
N1—C7—C6	113.37 (13)	C16—C17—H17	120.9
N3—C8—C9	120.41 (14)	N4—C18—C17	124.18 (17)
N3—C8—C13	117.62 (13)	N4—C18—H18	117.9
C9—C8—C13	121.88 (14)	C17—C18—H18	117.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···N3	0.86	1.94	2.624 (2)	136
C9—H9···N4	0.93	2.45	2.973 (2)	115

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H7⋯N3	0.86	1.94	2.624 (2)	136
C9—H9⋯N4	0.93	2.45	2.973 (2)	115