3-Penta-none 2,4-dinitro-phenyl-hydrazone.

Crystals of the title compound, C(11)H(14)N(4)O(4), were obtained from a condensation reaction of 2,4-dinitro-phenyl-hydrazine and 3-penta-none. In the crystal structure, the mol-ecule, except one methyl group, displays a nearly planar structure. The imino group links to the adjacent nitro group via intra-molecular hydrogen bonding. The partially overlapped arrangement and face-to-face separation of 3.410 (9) Å between parallel benzene rings indicate the existence of π-π stacking between adjacent mol-ecules. The crystal structure also contains weak inter-molecular C-H⋯O hydrogen bonding.

Related literature

For general background, see: Okabe et al. (1993 ▶); Shan et al. (2003 ▶); Shan et al. (2006 ▶). For related structures, see: Shan et al. (2008a ▶,b ▶); Cotton & Wilkinson (1972 ▶).

Experimental

Crystal data

C11H14N4O4

M = 266.26

Monoclinic,

a = 12.5298 (15) Å

b = 14.089 (2) Å

c = 7.3983 (8) Å

β = 93.235 (12)°

V = 1303.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 294 (2) K

0.31 × 0.29 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: none

10943 measured reflections

2543 independent reflections

1130 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.136

S = 1.01

2543 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016887/xu2428sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016887/xu2428Isup2.hkl

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

C11H14N4O4	F000 = 560
Mr = 266.26	Dx = 1.356 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 2556 reflections
a = 12.5298 (15) Å	θ = 3.5–25.0º
b = 14.089 (2) Å	µ = 0.11 mm−1
c = 7.3983 (8) Å	T = 294 (2) K
β = 93.235 (12)º	Prism, red
V = 1303.9 (3) Å3	0.31 × 0.29 × 0.22 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2543 independent reflections
Radiation source: fine-focus sealed tube	1130 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
Detector resolution: 10.00 pixels mm-1	θmax = 26.0º
T = 294(2) K	θmin = 3.1º
ω scans	h = −15→15
Absorption correction: none	k = −17→17
10943 measured reflections	l = −9→8

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0627P)2 + 0.0303P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.15 e Å−3
2543 reflections	Δρmin = −0.12 e Å−3
179 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.014 (2)
Secondary atom site location: difference Fourier map

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	0.49005 (19)	0.29067 (16)	0.0607 (3)	0.0817 (6)
N2	0.79233 (17)	0.4911 (2)	0.2228 (3)	0.0928 (7)
N3	0.35067 (15)	0.43228 (17)	0.2123 (3)	0.0742 (6)
N4	0.28589 (14)	0.50533 (14)	0.2635 (2)	0.0758 (6)
O1	0.39384 (16)	0.27125 (13)	0.0591 (3)	0.1056 (6)
O2	0.55348 (16)	0.23773 (14)	−0.0069 (3)	0.1145 (7)
O3	0.84951 (15)	0.42733 (18)	0.1731 (3)	0.1230 (8)
O4	0.82618 (14)	0.56837 (18)	0.2750 (3)	0.1248 (8)
C1	0.45801 (16)	0.44522 (16)	0.2116 (2)	0.0610 (6)
C2	0.52770 (16)	0.37825 (16)	0.1427 (2)	0.0636 (6)
C3	0.63704 (17)	0.39319 (17)	0.1474 (3)	0.0707 (6)
H3	0.6823	0.3478	0.1019	0.085*
C4	0.67726 (16)	0.47555 (18)	0.2196 (3)	0.0687 (6)
C5	0.61123 (17)	0.54410 (17)	0.2870 (3)	0.0696 (6)
H5	0.6402	0.6000	0.3352	0.083*
C6	0.50387 (17)	0.52968 (16)	0.2827 (3)	0.0665 (6)
H6	0.4599	0.5763	0.3275	0.080*
C7	0.18529 (19)	0.4892 (2)	0.2520 (3)	0.0854 (7)
C8	0.11384 (19)	0.5688 (2)	0.3035 (4)	0.1065 (9)
H8A	0.0615	0.5796	0.2040	0.128*
H8B	0.0752	0.5485	0.4068	0.128*
C9	0.1670 (2)	0.6608 (2)	0.3497 (4)	0.1228 (11)
H9A	0.2204	0.6513	0.4462	0.184*
H9B	0.1148	0.7054	0.3874	0.184*
H9C	0.2001	0.6851	0.2453	0.184*
C10	0.1317 (2)	0.3981 (2)	0.1833 (4)	0.1104 (10)
H10A	0.0593	0.4123	0.1380	0.132*
H10B	0.1703	0.3733	0.0836	0.132*
C11	0.1285 (3)	0.3250 (3)	0.3265 (4)	0.1350 (11)
H11A	0.2002	0.3082	0.3670	0.202*
H11B	0.0920	0.2697	0.2788	0.202*
H11C	0.0914	0.3496	0.4264	0.202*
H3N	0.3286 (18)	0.3785 (18)	0.167 (3)	0.092 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0977 (15)	0.0693 (15)	0.0780 (13)	0.0007 (13)	0.0042 (12)	−0.0036 (11)
N2	0.0699 (15)	0.116 (2)	0.0930 (15)	−0.0022 (14)	0.0047 (11)	0.0069 (14)
N3	0.0693 (13)	0.0696 (15)	0.0838 (13)	−0.0045 (12)	0.0044 (10)	0.0017 (11)
N4	0.0664 (12)	0.0779 (15)	0.0833 (12)	0.0052 (10)	0.0063 (9)	0.0082 (10)
O1	0.1008 (13)	0.0832 (14)	0.1323 (15)	−0.0184 (11)	0.0006 (11)	−0.0159 (11)
O2	0.1273 (15)	0.0911 (15)	0.1265 (16)	0.0073 (12)	0.0198 (12)	−0.0373 (12)
O3	0.0742 (11)	0.143 (2)	0.1533 (19)	0.0159 (12)	0.0156 (11)	−0.0054 (14)
O4	0.0865 (13)	0.138 (2)	0.1503 (18)	−0.0311 (13)	0.0091 (11)	−0.0206 (15)
C1	0.0659 (13)	0.0637 (16)	0.0532 (11)	−0.0012 (11)	0.0020 (10)	0.0093 (10)
C2	0.0733 (14)	0.0604 (15)	0.0570 (12)	0.0004 (12)	0.0022 (10)	0.0053 (11)
C3	0.0761 (15)	0.0749 (17)	0.0613 (13)	0.0131 (12)	0.0072 (11)	0.0077 (11)
C4	0.0618 (13)	0.0807 (17)	0.0637 (13)	−0.0006 (13)	0.0040 (10)	0.0075 (12)
C5	0.0746 (15)	0.0700 (16)	0.0637 (12)	−0.0068 (12)	0.0010 (11)	0.0018 (11)
C6	0.0700 (14)	0.0647 (15)	0.0647 (13)	0.0042 (11)	0.0043 (10)	0.0014 (11)
C7	0.0660 (15)	0.099 (2)	0.0907 (17)	−0.0043 (14)	0.0038 (12)	0.0060 (14)
C8	0.0719 (16)	0.124 (3)	0.124 (2)	0.0170 (17)	0.0121 (15)	0.0007 (19)
C9	0.104 (2)	0.103 (3)	0.163 (3)	0.0176 (18)	0.0196 (19)	−0.003 (2)
C10	0.0770 (17)	0.136 (3)	0.118 (2)	−0.0064 (17)	0.0036 (16)	0.002 (2)
C11	0.147 (3)	0.123 (3)	0.135 (3)	−0.027 (2)	0.015 (2)	−0.001 (2)

N1—O2	1.218 (2)	C5—H5	0.9300
N1—O1	1.235 (2)	C6—H6	0.9300
N1—C2	1.442 (3)	C7—C8	1.497 (4)
N2—O3	1.219 (3)	C7—C10	1.523 (4)
N2—O4	1.222 (3)	C8—C9	1.489 (4)
N2—C4	1.457 (3)	C8—H8A	0.9700
N3—C1	1.358 (3)	C8—H8B	0.9700
N3—N4	1.377 (3)	C9—H9A	0.9600
N3—H3N	0.87 (2)	C9—H9B	0.9600
N4—C7	1.279 (3)	C9—H9C	0.9600
C1—C2	1.401 (3)	C10—C11	1.479 (4)
C1—C6	1.410 (3)	C10—H10A	0.9700
C2—C3	1.385 (3)	C10—H10B	0.9700
C3—C4	1.362 (3)	C11—H11A	0.9600
C3—H3	0.9300	C11—H11B	0.9600
C4—C5	1.383 (3)	C11—H11C	0.9600
C5—C6	1.359 (3)
O2—N1—O1	121.3 (2)	N4—C7—C8	116.9 (2)
O2—N1—C2	119.4 (2)	N4—C7—C10	125.9 (2)
O1—N1—C2	119.3 (2)	C8—C7—C10	117.2 (2)
O3—N2—O4	123.5 (2)	C9—C8—C7	116.4 (2)
O3—N2—C4	118.8 (3)	C9—C8—H8A	108.2
O4—N2—C4	117.7 (3)	C7—C8—H8A	108.2
C1—N3—N4	120.0 (2)	C9—C8—H8B	108.2
C1—N3—H3N	114.2 (16)	C7—C8—H8B	108.2
N4—N3—H3N	125.4 (16)	H8A—C8—H8B	107.4
C7—N4—N3	116.3 (2)	C8—C9—H9A	109.5
N3—C1—C2	123.3 (2)	C8—C9—H9B	109.5
N3—C1—C6	119.7 (2)	H9A—C9—H9B	109.5
C2—C1—C6	117.06 (19)	C8—C9—H9C	109.5
C3—C2—C1	121.6 (2)	H9A—C9—H9C	109.5
C3—C2—N1	116.1 (2)	H9B—C9—H9C	109.5
C1—C2—N1	122.2 (2)	C11—C10—C7	112.2 (2)
C4—C3—C2	118.9 (2)	C11—C10—H10A	109.2
C4—C3—H3	120.6	C7—C10—H10A	109.2
C2—C3—H3	120.6	C11—C10—H10B	109.2
C3—C4—C5	121.4 (2)	C7—C10—H10B	109.2
C3—C4—N2	118.6 (2)	H10A—C10—H10B	107.9
C5—C4—N2	120.0 (2)	C10—C11—H11A	109.5
C6—C5—C4	119.9 (2)	C10—C11—H11B	109.5
C6—C5—H5	120.0	H11A—C11—H11B	109.5
C4—C5—H5	120.0	C10—C11—H11C	109.5
C5—C6—C1	121.1 (2)	H11A—C11—H11C	109.5
C5—C6—H6	119.4	H11B—C11—H11C	109.5
C1—C6—H6	119.4

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1	0.87 (2)	1.91 (2)	2.606 (3)	136 (2)
C5—H5···O1i	0.93	2.58	3.399 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1	0.87 (2)	1.91 (2)	2.606 (3)	136 (2)
C5—H5⋯O1i	0.93	2.58	3.399 (3)	147

Symmetry code: (i) .