N,N'-Bis(2-quinolylcarbon-yl)hydrazine.

The title compound, C(20)H(14)N(4)O(2), crystallizes in the ortho-rhom-bic system with a crystallographic twofold axis through the N-N bond. The mol-ecule is non-planar and the dihedral angle between two amide groups is 74.9 (2)°. An intra-molecular N-H⋯N hydrogen bond is present. In the crystal, the mol-ecules are packed in chains running along the c axis through inter-molecular N-H⋯O hydrogen bonds. These chains are further stabilized by inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions leading to the formation of a three-dimensional network.

Related literature

For general background to the chemistry of N,N′-diacyl­hydrazines, see: Zhao & Bruke (1997 ▶); Knödler et al. (2004 ▶); Bernhardt et al. (2005 ▶). For the syntheses and structures of related compounds, see: Jasinskas et al. (1975 ▶); Shao et al. (1999 ▶); Xu et al. (2006 ▶); Zheng et al. (2007 ▶); Shanmuga Sundara Raj et al. (2000 ▶). For the synthesis of the title compound, see: Xie et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶);

Experimental

Crystal data

C20H14N4O2

M = 342.35

Orthorhombic,

a = 11.649 (4) Å

b = 17.023 (6) Å

c = 8.349 (3) Å

V = 1655.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.26 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.976, T max = 0.993

10346 measured reflections

1629 independent reflections

816 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.115

S = 0.95

1629 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809037842/rz2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037842/rz2361Isup2.hkl

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

C20H14N4O2	F(000) = 712
Mr = 342.35	Dx = 1.374 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 28 reflections
a = 11.649 (4) Å	θ = 2.1–26.6°
b = 17.023 (6) Å	µ = 0.09 mm−1
c = 8.349 (3) Å	T = 296 K
V = 1655.6 (10) Å3	Block, colourless
Z = 4	0.26 × 0.12 × 0.08 mm

Bruker APEXII CCD diffractometer	1629 independent reflections
Radiation source: fine-focus sealed tube	816 reflections with I > 2σ(I)
graphite	Rint = 0.082
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.976, Tmax = 0.993	k = −21→18
10346 measured reflections	l = −9→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0525P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max < 0.001
1629 reflections	Δρmax = 0.17 e Å−3
119 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

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	0.61559 (14)	0.28662 (9)	0.3812 (2)	0.0651 (5)
N1	0.69622 (14)	0.44375 (10)	0.1318 (2)	0.0424 (5)
N2	0.73777 (18)	0.28973 (9)	0.1733 (2)	0.0605 (6)
H2A	0.7745	0.3197	0.1080	0.073*
C1	0.62868 (17)	0.40522 (13)	0.2314 (3)	0.0432 (6)
C2	0.52811 (18)	0.43630 (14)	0.2994 (3)	0.0520 (7)
H2B	0.4841	0.4063	0.3694	0.062*
C3	0.49611 (18)	0.51056 (15)	0.2615 (3)	0.0549 (7)
H3A	0.4290	0.5317	0.3037	0.066*
C4	0.56521 (18)	0.55552 (12)	0.1576 (3)	0.0450 (6)
C5	0.5394 (2)	0.63312 (13)	0.1127 (3)	0.0599 (7)
H5A	0.4739	0.6573	0.1530	0.072*
C6	0.6091 (2)	0.67300 (14)	0.0114 (3)	0.0663 (8)
H6A	0.5908	0.7243	−0.0172	0.080*
C7	0.7083 (2)	0.63781 (14)	−0.0508 (3)	0.0615 (7)
H7A	0.7552	0.6658	−0.1205	0.074*
C8	0.73620 (19)	0.56297 (13)	−0.0097 (3)	0.0498 (6)
H8A	0.8025	0.5401	−0.0509	0.060*
C9	0.66544 (17)	0.51985 (12)	0.0947 (3)	0.0401 (6)
C10	0.65956 (19)	0.32223 (14)	0.2702 (3)	0.0471 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0692 (11)	0.0517 (10)	0.0743 (13)	−0.0141 (9)	0.0059 (10)	0.0116 (10)
N1	0.0396 (11)	0.0382 (11)	0.0495 (12)	−0.0009 (8)	−0.0004 (9)	−0.0006 (9)
N2	0.0861 (15)	0.0349 (10)	0.0605 (14)	0.0080 (12)	0.0094 (12)	0.0031 (10)
C1	0.0407 (13)	0.0388 (13)	0.0501 (15)	−0.0023 (11)	−0.0059 (11)	−0.0051 (11)
C2	0.0404 (14)	0.0547 (17)	0.0610 (17)	−0.0066 (12)	0.0063 (12)	−0.0029 (13)
C3	0.0387 (13)	0.0605 (18)	0.0657 (17)	0.0031 (12)	0.0043 (12)	−0.0063 (14)
C4	0.0379 (13)	0.0428 (14)	0.0543 (16)	0.0046 (10)	−0.0049 (11)	−0.0065 (12)
C5	0.0508 (15)	0.0484 (16)	0.080 (2)	0.0138 (13)	−0.0026 (14)	−0.0058 (15)
C6	0.0691 (18)	0.0403 (15)	0.089 (2)	0.0079 (13)	−0.0075 (16)	0.0060 (15)
C7	0.0599 (16)	0.0489 (16)	0.076 (2)	−0.0021 (13)	0.0032 (14)	0.0091 (14)
C8	0.0459 (14)	0.0458 (15)	0.0577 (16)	0.0004 (11)	0.0014 (11)	0.0027 (12)
C9	0.0362 (12)	0.0358 (12)	0.0483 (14)	0.0012 (10)	−0.0064 (11)	−0.0033 (11)
C10	0.0489 (14)	0.0433 (15)	0.0491 (15)	−0.0100 (12)	−0.0030 (12)	−0.0013 (12)

O1—C10	1.220 (3)	C3—H3A	0.9300
N1—C1	1.319 (3)	C4—C5	1.406 (3)
N1—C9	1.379 (2)	C4—C9	1.417 (3)
N2—C10	1.338 (3)	C5—C6	1.354 (3)
N2—N2i	1.382 (3)	C5—H5A	0.9300
N2—H2A	0.8600	C6—C7	1.401 (3)
C1—C2	1.405 (3)	C6—H6A	0.9300
C1—C10	1.493 (3)	C7—C8	1.359 (3)
C2—C3	1.355 (3)	C7—H7A	0.9300
C2—H2B	0.9300	C8—C9	1.406 (3)
C3—C4	1.409 (3)	C8—H8A	0.9300
C1—N1—C9	116.98 (18)	C6—C5—H5A	119.7
C10—N2—N2i	123.0 (2)	C4—C5—H5A	119.7
C10—N2—H2A	118.5	C5—C6—C7	120.7 (2)
N2i—N2—H2A	118.5	C5—C6—H6A	119.6
N1—C1—C2	124.4 (2)	C7—C6—H6A	119.6
N1—C1—C10	117.6 (2)	C8—C7—C6	120.3 (2)
C2—C1—C10	118.0 (2)	C8—C7—H7A	119.8
C3—C2—C1	119.1 (2)	C6—C7—H7A	119.8
C3—C2—H2B	120.5	C7—C8—C9	120.3 (2)
C1—C2—H2B	120.5	C7—C8—H8A	119.8
C2—C3—C4	119.5 (2)	C9—C8—H8A	119.8
C2—C3—H3A	120.2	N1—C9—C8	118.5 (2)
C4—C3—H3A	120.2	N1—C9—C4	122.2 (2)
C5—C4—C3	123.5 (2)	C8—C9—C4	119.3 (2)
C5—C4—C9	118.7 (2)	O1—C10—N2	122.7 (2)
C3—C4—C9	117.8 (2)	O1—C10—C1	122.3 (2)
C6—C5—C4	120.6 (2)	N2—C10—C1	115.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1	0.86	2.31	2.689 (2)	107
N2—H2A···O1ii	0.86	2.35	2.978 (3)	130
C5—H5A···O1iii	0.93	2.45	3.177 (3)	135
C8—H8A···Cg1iv	0.93	2.64	3.449	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1	0.86	2.31	2.689 (2)	107
N2—H2A⋯O1ii	0.86	2.35	2.978 (3)	130
C5—H5A⋯O1iii	0.93	2.45	3.177 (3)	135
C8—H8A⋯Cg1iv	0.93	2.64	3.449	146

Symmetry codes: (ii) ; (iii) ; (iv) . Cg1 is the centroid of the N1/C1–C4/C9 ring.