(E)-1-(2,4-Dinitro-phen-yl)-2-pentyl-idenehydrazine.

The title compound, C(11)H(14)N(4)O(4), is essentially planar with an r.m.s. deviation for the 19 non-H atoms of 0.152 Å. The conformation about the C=N bond is E, and the mol-ecule has a U-shape as the butyl group folds over towards the aromatic system. An intra-molecular C-H⋯N inter-action occurs. The crystal packing is dominated by N-H⋯O hydrogen bonding and C-H⋯O contacts, leading to twisted zigzag supra-molecular chains along the c direction. The crystal packing brings two nitro O atoms into an unusually close proximity of 2.686 (4) Å. While the nature of this inter-action is not obvious, there are several precendents for such short nitro-nitro O⋯O contacts of less than 2.70 Å in the crystallographic literature.

Related literature

For background to the biological uses of hydrazones, see: Rollas & Küçükgüzel (2007 ▶). For background to the synthesis, see: Furniss et al. (1999 ▶); Neuenfeldt et al. (2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C11H14N4O4

M = 266.26

Monoclinic,

a = 31.162 (3) Å

b = 4.4930 (4) Å

c = 18.7329 (14) Å

β = 106.159 (4)°

V = 2519.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 120 K

0.32 × 0.03 × 0.02 mm

Data collection

-Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.628, T max = 1.000

8172 measured reflections

2174 independent reflections

1451 reflections with I > 2σ(I)

R int = 0.115

Refinement

R[F 2 > 2σ(F 2)] = 0.078

wR(F 2) = 0.183

S = 1.10

2174 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002102/fj2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002102/fj2271Isup2.hkl

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

C11H14N4O4	F(000) = 1120
Mr = 266.26	Dx = 1.404 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 14843 reflections
a = 31.162 (3) Å	θ = 2.9–27.5°
b = 4.4930 (4) Å	µ = 0.11 mm−1
c = 18.7329 (14) Å	T = 120 K
β = 106.159 (4)°	Needle, yellow
V = 2519.2 (4) Å3	0.32 × 0.03 × 0.02 mm
Z = 8

-Nonius KappaCCD area-detector diffractometer	2174 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1451 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.115
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −36→36
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −5→5
Tmin = 0.628, Tmax = 1.000	l = −22→22
8172 measured reflections

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0406P)2 + 14.6755P] where P = (Fo2 + 2Fc2)/3
2174 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.04985 (11)	−0.5722 (7)	0.23571 (16)	0.0294 (8)
O2	0.11770 (10)	−0.4264 (8)	0.24360 (16)	0.0360 (9)
O3	−0.03340 (10)	−0.1033 (7)	0.37999 (16)	0.0263 (8)
O4	−0.00644 (9)	0.2652 (7)	0.45386 (15)	0.0240 (7)
N1	0.07910 (11)	0.3841 (8)	0.49031 (18)	0.0194 (8)
H1N	0.0551 (14)	0.401 (10)	0.505 (2)	0.023*
N2	0.11897 (11)	0.5276 (8)	0.52633 (18)	0.0224 (9)
N3	0.08254 (13)	−0.4163 (9)	0.26201 (19)	0.0267 (9)
N4	−0.00244 (11)	0.0661 (8)	0.41033 (19)	0.0213 (8)
C1	0.07833 (13)	0.2003 (10)	0.4333 (2)	0.0197 (10)
C2	0.04022 (13)	0.0353 (10)	0.3940 (2)	0.0185 (9)
C3	0.04158 (14)	−0.1701 (9)	0.3391 (2)	0.0191 (9)
H3	0.0161	−0.2868	0.3159	0.023*
C4	0.08074 (14)	−0.2003 (10)	0.3192 (2)	0.0222 (10)
C5	0.11852 (14)	−0.0324 (10)	0.3534 (2)	0.0242 (10)
H5	0.1450	−0.0528	0.3381	0.029*
C6	0.11736 (14)	0.1613 (10)	0.4090 (2)	0.0230 (10)
H6	0.1434	0.2733	0.4321	0.028*
C7	0.11826 (14)	0.6629 (11)	0.5855 (2)	0.0248 (10)
H7	0.0922 (15)	0.660 (11)	0.604 (2)	0.030*
C8	0.15800 (14)	0.8254 (11)	0.6307 (2)	0.0281 (11)
H8A	0.1693	0.7207	0.6788	0.034*
H8B	0.1485	1.0266	0.6415	0.034*
C9	0.19629 (14)	0.8581 (12)	0.5957 (2)	0.0292 (11)
H9A	0.2041	0.6593	0.5802	0.035*
H9B	0.1863	0.9830	0.5505	0.035*
C10	0.23763 (15)	0.9966 (13)	0.6476 (3)	0.0382 (13)
H10A	0.2293	1.1896	0.6655	0.046*
H10B	0.2485	0.8654	0.6914	0.046*
C11	0.27528 (16)	1.0479 (14)	0.6126 (3)	0.0481 (15)
H11A	0.2826	0.8602	0.5921	0.072*
H11B	0.3016	1.1216	0.6503	0.072*
H11C	0.2660	1.1951	0.5727	0.072*

	U11	U22	U33	U12	U13	U23
O1	0.0374 (18)	0.0244 (18)	0.0233 (16)	0.0013 (17)	0.0035 (14)	−0.0058 (15)
O2	0.0333 (18)	0.050 (2)	0.0308 (17)	0.0130 (18)	0.0186 (15)	−0.0036 (17)
O3	0.0273 (16)	0.0281 (19)	0.0246 (15)	−0.0065 (15)	0.0090 (13)	−0.0059 (15)
O4	0.0244 (16)	0.0223 (18)	0.0265 (15)	0.0017 (13)	0.0093 (13)	−0.0074 (15)
N1	0.0163 (18)	0.019 (2)	0.0236 (18)	0.0000 (16)	0.0061 (15)	−0.0035 (17)
N2	0.0181 (17)	0.026 (2)	0.0231 (19)	−0.0029 (16)	0.0052 (15)	0.0018 (17)
N3	0.037 (2)	0.023 (2)	0.0218 (19)	0.010 (2)	0.0108 (18)	0.0006 (17)
N4	0.0228 (19)	0.020 (2)	0.0219 (18)	0.0005 (17)	0.0078 (16)	0.0023 (18)
C1	0.022 (2)	0.017 (2)	0.019 (2)	0.0026 (19)	0.0042 (18)	0.0026 (19)
C2	0.019 (2)	0.017 (2)	0.019 (2)	−0.0002 (18)	0.0047 (18)	0.0006 (19)
C3	0.024 (2)	0.010 (2)	0.021 (2)	0.0042 (18)	0.0025 (18)	0.0015 (18)
C4	0.029 (2)	0.018 (2)	0.021 (2)	0.005 (2)	0.0091 (19)	0.0028 (19)
C5	0.022 (2)	0.025 (3)	0.028 (2)	0.005 (2)	0.0105 (19)	0.009 (2)
C6	0.019 (2)	0.022 (3)	0.028 (2)	−0.0008 (19)	0.0082 (19)	0.006 (2)
C7	0.023 (2)	0.027 (3)	0.024 (2)	−0.004 (2)	0.0054 (19)	−0.003 (2)
C8	0.030 (2)	0.028 (3)	0.027 (2)	−0.008 (2)	0.009 (2)	−0.005 (2)
C9	0.027 (2)	0.033 (3)	0.027 (2)	−0.006 (2)	0.006 (2)	0.001 (2)
C10	0.032 (3)	0.043 (4)	0.033 (3)	−0.010 (2)	−0.002 (2)	0.004 (3)
C11	0.032 (3)	0.056 (4)	0.054 (3)	−0.008 (3)	0.009 (3)	0.010 (3)

O1—N3	1.221 (5)	C5—H5	0.9500
O2—N3	1.238 (4)	C6—H6	0.9500
O3—N4	1.236 (4)	C7—C8	1.483 (6)
O4—N4	1.240 (4)	C7—H7	0.96 (4)
N1—C1	1.345 (5)	C8—C9	1.521 (6)
N1—N2	1.396 (5)	C8—H8A	0.9900
N1—H1N	0.87 (4)	C8—H8B	0.9900
N2—C7	1.270 (5)	C9—C10	1.515 (6)
N3—C4	1.458 (5)	C9—H9A	0.9900
N4—C2	1.451 (5)	C9—H9B	0.9900
C1—C2	1.420 (6)	C10—C11	1.513 (6)
C1—C6	1.423 (5)	C10—H10A	0.9900
C2—C3	1.391 (6)	C10—H10B	0.9900
C3—C4	1.378 (5)	C11—H11A	0.9800
C3—H3	0.9500	C11—H11B	0.9800
C4—C5	1.395 (6)	C11—H11C	0.9800
C5—C6	1.365 (6)
C1—N1—N2	118.9 (3)	N2—C7—C8	121.3 (4)
C1—N1—H1N	119 (3)	N2—C7—H7	122 (3)
N2—N1—H1N	122 (3)	C8—C7—H7	117 (3)
C7—N2—N1	114.4 (3)	C7—C8—C9	115.5 (4)
O1—N3—O2	124.8 (4)	C7—C8—H8A	108.4
O1—N3—C4	118.7 (3)	C9—C8—H8A	108.4
O2—N3—C4	116.6 (4)	C7—C8—H8B	108.4
O3—N4—O4	122.6 (3)	C9—C8—H8B	108.4
O3—N4—C2	119.2 (3)	H8A—C8—H8B	107.5
O4—N4—C2	118.2 (3)	C10—C9—C8	113.0 (4)
N1—C1—C2	124.0 (4)	C10—C9—H9A	109.0
N1—C1—C6	120.1 (4)	C8—C9—H9A	109.0
C2—C1—C6	115.8 (4)	C10—C9—H9B	109.0
C3—C2—C1	122.5 (4)	C8—C9—H9B	109.0
C3—C2—N4	115.9 (4)	H9A—C9—H9B	107.8
C1—C2—N4	121.6 (4)	C11—C10—C9	114.0 (4)
C4—C3—C2	118.5 (4)	C11—C10—H10A	108.7
C4—C3—H3	120.8	C9—C10—H10A	108.7
C2—C3—H3	120.8	C11—C10—H10B	108.7
C3—C4—C5	121.3 (4)	C9—C10—H10B	108.7
C3—C4—N3	118.8 (4)	H10A—C10—H10B	107.6
C5—C4—N3	119.8 (4)	C10—C11—H11A	109.5
C6—C5—C4	119.8 (4)	C10—C11—H11B	109.5
C6—C5—H5	120.1	H11A—C11—H11B	109.5
C4—C5—H5	120.1	C10—C11—H11C	109.5
C5—C6—C1	121.9 (4)	H11A—C11—H11C	109.5
C5—C6—H6	119.0	H11B—C11—H11C	109.5
C1—C6—H6	119.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O4	0.87 (4)	1.99 (4)	2.616 (5)	128 (3)
N1—H1n···O4i	0.87 (4)	2.41 (4)	3.166 (5)	146 (4)
C3—H3···O1ii	0.95	2.39	3.335 (5)	176
C6—H6···N2	0.95	2.40	2.735 (5)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O4	0.87 (4)	1.99 (4)	2.616 (5)	128 (3)
N1—H1n⋯O4i	0.87 (4)	2.41 (4)	3.166 (5)	146 (4)
C3—H3⋯O1ii	0.95	2.39	3.335 (5)	176
C6—H6⋯N2	0.95	2.40	2.735 (5)	100

Symmetry codes: (i) ; (ii) .