2-Nitro-N'-[1-(pyridin-2-yl)ethyl-idene]benzohydrazide.

In the title compound, C(14)H(12)N(4)O(3), the dihedral angle between the benzene ring and the pyridine ring is 60.9 (2)°. The major twist in the mol-ecule occurs about the (NH)-(CO)-C(ar)-C(ar) (ar = aromatic) bond, the relevant torsion angle being 63.97 (12)°. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For related structures, see: Mangalam et al. (2009 ▶); Tang (2011 ▶).

Experimental

Crystal data

C14H12N4O3

M = 284.28

Monoclinic,

a = 10.8303 (8) Å

b = 8.9112 (7) Å

c = 14.9437 (11) Å

β = 101.483 (1)°

V = 1413.36 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.983

7984 measured reflections

3048 independent reflections

2358 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.126

S = 1.05

3048 reflections

194 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811049257/hb6488sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049257/hb6488Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049257/hb6488Isup3.cml

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

C14H12N4O3	F(000) = 592
Mr = 284.28	Dx = 1.336 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3300 reflections
a = 10.8303 (8) Å	θ = 2.6–28.3°
b = 8.9112 (7) Å	µ = 0.10 mm−1
c = 14.9437 (11) Å	T = 298 K
β = 101.483 (1)°	Block, yellow
V = 1413.36 (18) Å3	0.20 × 0.20 × 0.18 mm
Z = 4

Bruker SMART 1K CCD diffractometer	3048 independent reflections
Radiation source: fine-focus sealed tube	2358 reflections with I > 2σ(I)
graphite	Rint = 0.015
ω scan	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→9
Tmin = 0.981, Tmax = 0.983	k = −11→11
7984 measured reflections	l = −18→19

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.2704P] where P = (Fo2 + 2Fc2)/3
3048 reflections	(Δ/σ)max < 0.001
194 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.19 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	0.12218 (13)	1.12660 (15)	0.19162 (9)	0.0549 (3)
N2	0.13344 (11)	0.83590 (12)	0.03440 (8)	0.0444 (3)
N3	0.09007 (12)	0.69373 (13)	0.00993 (8)	0.0476 (3)
N4	0.39424 (14)	0.72128 (18)	0.02669 (11)	0.0702 (4)
O1	0.09268 (11)	0.50167 (12)	−0.08683 (8)	0.0591 (3)
O2	0.47052 (19)	0.8063 (2)	0.07159 (12)	0.1265 (8)
O3	0.36144 (14)	0.60537 (16)	0.05665 (10)	0.0845 (4)
C1	0.14756 (12)	1.05765 (15)	0.11797 (9)	0.0416 (3)
C2	0.21742 (15)	1.12613 (17)	0.06083 (11)	0.0535 (4)
H2	0.2356	1.0747	0.0109	0.064*
C3	0.25946 (17)	1.27091 (18)	0.07897 (13)	0.0629 (4)
H3A	0.3046	1.3194	0.0407	0.075*
C4	0.23368 (17)	1.34274 (18)	0.15460 (12)	0.0631 (5)
H4	0.2610	1.4404	0.1686	0.076*
C5	0.16671 (18)	1.26654 (19)	0.20863 (12)	0.0641 (5)
H5	0.1510	1.3147	0.2604	0.077*
C6	0.09516 (13)	0.90373 (15)	0.09935 (9)	0.0416 (3)
C7	0.00521 (17)	0.8435 (2)	0.15426 (12)	0.0616 (4)
H7A	−0.0685	0.8058	0.1140	0.092*
H7B	−0.0185	0.9222	0.1914	0.092*
H7C	0.0448	0.7637	0.1928	0.092*
C8	0.13068 (14)	0.62602 (15)	−0.05927 (10)	0.0452 (3)
C9	0.21832 (14)	0.71408 (15)	−0.10665 (10)	0.0460 (3)
C10	0.33825 (15)	0.76293 (16)	−0.06705 (11)	0.0519 (4)
C11	0.41041 (18)	0.8496 (2)	−0.11371 (14)	0.0666 (5)
H11	0.4896	0.8832	−0.0848	0.080*
C12	0.3637 (2)	0.8853 (2)	−0.20298 (15)	0.0751 (6)
H12	0.4120	0.9420	−0.2354	0.090*
C13	0.2465 (2)	0.8381 (2)	−0.24480 (14)	0.0759 (6)
H13	0.2152	0.8628	−0.3055	0.091*
C14	0.17386 (18)	0.7532 (2)	−0.19668 (11)	0.0611 (4)
H14	0.0939	0.7221	−0.2257	0.073*
H3	0.0368 (15)	0.640 (2)	0.0371 (13)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0659 (8)	0.0473 (7)	0.0524 (7)	−0.0064 (6)	0.0134 (6)	−0.0128 (6)
N2	0.0521 (7)	0.0348 (6)	0.0491 (7)	−0.0093 (5)	0.0172 (5)	−0.0071 (5)
N3	0.0570 (7)	0.0385 (6)	0.0534 (7)	−0.0140 (5)	0.0257 (6)	−0.0098 (5)
N4	0.0666 (9)	0.0687 (10)	0.0739 (10)	−0.0229 (8)	0.0109 (8)	0.0082 (8)
O1	0.0779 (8)	0.0422 (6)	0.0646 (7)	−0.0196 (5)	0.0320 (6)	−0.0173 (5)
O2	0.1304 (14)	0.1325 (16)	0.0997 (12)	−0.0800 (12)	−0.0180 (11)	0.0141 (11)
O3	0.0905 (10)	0.0725 (9)	0.0852 (9)	−0.0211 (7)	0.0049 (7)	0.0280 (7)
C1	0.0429 (7)	0.0365 (7)	0.0433 (7)	−0.0008 (5)	0.0038 (5)	−0.0034 (5)
C2	0.0646 (9)	0.0412 (8)	0.0570 (9)	−0.0072 (7)	0.0176 (7)	−0.0042 (7)
C3	0.0719 (11)	0.0439 (9)	0.0733 (11)	−0.0115 (7)	0.0154 (9)	0.0046 (8)
C4	0.0726 (11)	0.0378 (8)	0.0733 (11)	−0.0093 (7)	0.0007 (9)	−0.0071 (8)
C5	0.0777 (11)	0.0503 (9)	0.0618 (10)	−0.0057 (8)	0.0077 (8)	−0.0203 (8)
C6	0.0445 (7)	0.0398 (7)	0.0410 (7)	−0.0042 (5)	0.0094 (5)	−0.0038 (5)
C7	0.0698 (10)	0.0616 (10)	0.0604 (10)	−0.0224 (8)	0.0298 (8)	−0.0164 (8)
C8	0.0539 (8)	0.0367 (7)	0.0481 (8)	−0.0081 (6)	0.0179 (6)	−0.0062 (6)
C9	0.0601 (8)	0.0325 (7)	0.0516 (8)	−0.0031 (6)	0.0258 (7)	−0.0049 (6)
C10	0.0611 (9)	0.0394 (8)	0.0607 (9)	−0.0077 (6)	0.0255 (7)	0.0005 (7)
C11	0.0694 (11)	0.0533 (10)	0.0869 (13)	−0.0105 (8)	0.0394 (10)	0.0058 (9)
C12	0.0996 (15)	0.0567 (11)	0.0852 (13)	−0.0009 (10)	0.0576 (12)	0.0125 (9)
C13	0.1131 (17)	0.0669 (12)	0.0576 (10)	0.0116 (11)	0.0404 (11)	0.0133 (9)
C14	0.0751 (11)	0.0581 (10)	0.0540 (10)	0.0025 (8)	0.0225 (8)	−0.0023 (7)

N1—C1	1.3360 (18)	C4—H4	0.9300
N1—C5	1.343 (2)	C5—H5	0.9300
N2—C6	1.2805 (17)	C6—C7	1.493 (2)
N2—N3	1.3752 (15)	C7—H7A	0.9600
N3—C8	1.3446 (18)	C7—H7B	0.9600
N3—H3	0.903 (9)	C7—H7C	0.9600
N4—O3	1.2071 (19)	C8—C9	1.5118 (19)
N4—O2	1.219 (2)	C9—C14	1.380 (2)
N4—C10	1.459 (2)	C9—C10	1.386 (2)
O1—C8	1.2245 (16)	C10—C11	1.382 (2)
C1—C2	1.390 (2)	C11—C12	1.367 (3)
C1—C6	1.4892 (19)	C11—H11	0.9300
C2—C3	1.377 (2)	C12—C13	1.365 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.375 (3)	C13—C14	1.391 (3)
C3—H3A	0.9300	C13—H13	0.9300
C4—C5	1.368 (3)	C14—H14	0.9300
C1—N1—C5	117.26 (14)	C6—C7—H7B	109.5
C6—N2—N3	119.44 (11)	H7A—C7—H7B	109.5
C8—N3—N2	118.11 (11)	C6—C7—H7C	109.5
C8—N3—H3	116.5 (13)	H7A—C7—H7C	109.5
N2—N3—H3	125.4 (13)	H7B—C7—H7C	109.5
O3—N4—O2	123.02 (17)	O1—C8—N3	121.68 (13)
O3—N4—C10	118.49 (14)	O1—C8—C9	120.83 (12)
O2—N4—C10	118.48 (15)	N3—C8—C9	117.34 (11)
N1—C1—C2	122.05 (13)	C14—C9—C10	116.89 (14)
N1—C1—C6	116.38 (12)	C14—C9—C8	117.24 (14)
C2—C1—C6	121.56 (12)	C10—C9—C8	125.84 (14)
C3—C2—C1	119.31 (15)	C11—C10—C9	122.42 (16)
C3—C2—H2	120.3	C11—C10—N4	117.24 (15)
C1—C2—H2	120.3	C9—C10—N4	120.33 (13)
C4—C3—C2	119.00 (16)	C12—C11—C10	119.04 (18)
C4—C3—H3A	120.5	C12—C11—H11	120.5
C2—C3—H3A	120.5	C10—C11—H11	120.5
C5—C4—C3	118.18 (15)	C13—C12—C11	120.35 (17)
C5—C4—H4	120.9	C13—C12—H12	119.8
C3—C4—H4	120.9	C11—C12—H12	119.8
N1—C5—C4	124.17 (16)	C12—C13—C14	120.08 (18)
N1—C5—H5	117.9	C12—C13—H13	120.0
C4—C5—H5	117.9	C14—C13—H13	120.0
N2—C6—C1	114.05 (12)	C9—C14—C13	121.19 (18)
N2—C6—C7	126.30 (12)	C9—C14—H14	119.4
C1—C6—C7	119.65 (12)	C13—C14—H14	119.4
C6—C7—H7A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1i	0.90 (1)	2.13 (1)	3.0290 (15)	173.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1i	0.90 (1)	2.13 (1)	3.0290 (15)	173 (2)

Symmetry code: (i) .