(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(2-nitro-phen-yl)ethyl-idene]hydrazine.

The title compound, C(14)H(11)N(5)O(6), was obtained from the condensation reaction of 2,4-dinitro-phenyl-hydrazine and 2-nitro-acetophenone. The mol-ecule displays an E conformation about the C=N double bond and an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. The dihedral angle between the benzene rings is 7.84 (6)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and π-π stacking inter-actions [centroid-centroid distance = 3.6447 (8) Å] into a three-dimensional network.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2011 ▶); Shan et al. (2003 ▶). For background to and the physiological and biological activity of hydro­zones, see: Bendre et al. (1998 ▶); Nakamura & Goto (1996 ▶); Rollas & Küçükgüzel (2007 ▶); Singh et al. (2005 ▶); Yacorb (1999 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H11N5O6

M = 345.28

Monoclinic,

a = 11.9313 (9) Å

b = 8.6700 (7) Å

c = 15.2363 (9) Å

β = 112.455 (5)°

V = 1456.61 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 100 K

0.40 × 0.16 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.951, T max = 0.984

16360 measured reflections

4244 independent reflections

3361 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.04

4244 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811042620/rz2643sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042620/rz2643Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042620/rz2643Isup3.cml

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

C14H11N5O6	F(000) = 712
Mr = 345.28	Dx = 1.574 Mg m−3
Monoclinic, P21/c	Melting point = 443–444 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.9313 (9) Å	Cell parameters from 4244 reflections
b = 8.6700 (7) Å	θ = 1.9–30.0°
c = 15.2363 (9) Å	µ = 0.13 mm−1
β = 112.455 (5)°	T = 100 K
V = 1456.61 (19) Å3	Block, yellow
Z = 4	0.40 × 0.16 × 0.13 mm

Bruker APEXII CCD area-detector diffractometer	4244 independent reflections
Radiation source: sealed tube	3361 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
Tmin = 0.951, Tmax = 0.984	k = −9→12
16360 measured reflections	l = −21→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0493P)2 + 0.498P] where P = (Fo2 + 2Fc2)/3
4244 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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	1.32132 (8)	0.59779 (12)	0.77977 (6)	0.0221 (2)
O2	1.14527 (9)	0.70362 (12)	0.74461 (6)	0.0233 (2)
O3	1.44309 (8)	0.36901 (13)	0.55130 (7)	0.0265 (2)
O4	1.33701 (8)	0.39821 (12)	0.40099 (6)	0.0229 (2)
O5	0.76820 (8)	0.73691 (11)	0.30121 (6)	0.0191 (2)
O6	0.87386 (8)	0.93847 (12)	0.29701 (6)	0.0200 (2)
N1	1.01173 (9)	0.76742 (13)	0.56858 (7)	0.0166 (2)
H1	1.0252	0.7860	0.6283	0.020*
N2	0.91649 (9)	0.83451 (13)	0.49714 (7)	0.0160 (2)
N3	1.22384 (9)	0.64213 (13)	0.72129 (7)	0.0168 (2)
N4	1.35479 (9)	0.42076 (13)	0.48519 (7)	0.0168 (2)
N5	0.79296 (9)	0.87393 (13)	0.31434 (7)	0.0147 (2)
C1	1.09536 (10)	0.68522 (15)	0.54842 (8)	0.0145 (2)
C2	1.19951 (11)	0.62140 (14)	0.62097 (8)	0.0143 (2)
C3	1.28425 (10)	0.53651 (14)	0.59994 (8)	0.0151 (2)
H3A	1.3523	0.4966	0.6483	0.018*
C4	1.26628 (10)	0.51219 (15)	0.50638 (8)	0.0151 (2)
C5	1.16558 (11)	0.57308 (15)	0.43212 (8)	0.0170 (2)
H5A	1.1555	0.5560	0.3693	0.020*
C6	1.08201 (11)	0.65806 (16)	0.45296 (8)	0.0171 (2)
H6A	1.0153	0.6987	0.4037	0.021*
C7	0.83449 (11)	0.89627 (15)	0.52181 (8)	0.0152 (2)
C8	0.73396 (10)	0.97562 (15)	0.44578 (8)	0.0156 (2)
C9	0.71612 (10)	0.97024 (14)	0.34927 (8)	0.0143 (2)
C10	0.62471 (11)	1.04965 (15)	0.27935 (9)	0.0182 (3)
H10A	0.6165	1.0430	0.2163	0.022*
C11	0.54516 (11)	1.13956 (16)	0.30456 (10)	0.0207 (3)
H11A	0.4835	1.1942	0.2585	0.025*
C12	0.55861 (11)	1.14699 (17)	0.39886 (10)	0.0214 (3)
H12A	0.5048	1.2056	0.4159	0.026*
C13	0.65176 (11)	1.06765 (16)	0.46806 (9)	0.0192 (3)
H13A	0.6600	1.0757	0.5311	0.023*
C14	0.83892 (12)	0.89321 (17)	0.62186 (9)	0.0212 (3)
H14A	0.8708	0.7959	0.6507	0.032*
H14B	0.7586	0.9067	0.6209	0.032*
H14C	0.8902	0.9750	0.6578	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0217 (4)	0.0283 (6)	0.0134 (4)	0.0021 (4)	0.0035 (3)	0.0030 (4)
O2	0.0306 (5)	0.0261 (6)	0.0165 (4)	0.0090 (4)	0.0126 (4)	0.0021 (4)
O3	0.0211 (4)	0.0347 (6)	0.0202 (5)	0.0117 (4)	0.0041 (4)	0.0004 (4)
O4	0.0234 (4)	0.0294 (6)	0.0170 (4)	0.0045 (4)	0.0091 (4)	−0.0032 (4)
O5	0.0240 (4)	0.0140 (5)	0.0189 (4)	−0.0013 (4)	0.0079 (4)	−0.0031 (3)
O6	0.0177 (4)	0.0241 (5)	0.0204 (4)	−0.0010 (4)	0.0098 (3)	0.0028 (4)
N1	0.0187 (5)	0.0190 (6)	0.0121 (4)	0.0042 (4)	0.0059 (4)	0.0001 (4)
N2	0.0165 (4)	0.0168 (6)	0.0141 (4)	0.0026 (4)	0.0053 (4)	0.0002 (4)
N3	0.0218 (5)	0.0157 (6)	0.0134 (4)	0.0002 (4)	0.0074 (4)	0.0019 (4)
N4	0.0160 (4)	0.0171 (6)	0.0177 (5)	0.0008 (4)	0.0070 (4)	−0.0014 (4)
N5	0.0150 (4)	0.0171 (6)	0.0113 (4)	0.0008 (4)	0.0042 (4)	0.0006 (4)
C1	0.0166 (5)	0.0130 (6)	0.0147 (5)	−0.0006 (4)	0.0067 (4)	−0.0006 (4)
C2	0.0178 (5)	0.0138 (6)	0.0116 (5)	−0.0004 (4)	0.0060 (4)	0.0009 (4)
C3	0.0156 (5)	0.0140 (6)	0.0151 (5)	−0.0008 (4)	0.0053 (4)	0.0013 (4)
C4	0.0159 (5)	0.0146 (6)	0.0160 (5)	0.0006 (4)	0.0073 (4)	−0.0005 (4)
C5	0.0193 (5)	0.0185 (7)	0.0133 (5)	0.0008 (5)	0.0065 (4)	−0.0008 (5)
C6	0.0183 (5)	0.0192 (7)	0.0128 (5)	0.0024 (5)	0.0047 (4)	−0.0003 (5)
C7	0.0186 (5)	0.0128 (6)	0.0164 (5)	−0.0011 (4)	0.0091 (4)	−0.0011 (4)
C8	0.0155 (5)	0.0143 (6)	0.0182 (5)	−0.0016 (4)	0.0078 (4)	−0.0018 (4)
C9	0.0135 (5)	0.0119 (6)	0.0183 (5)	−0.0013 (4)	0.0070 (4)	−0.0026 (4)
C10	0.0166 (5)	0.0175 (7)	0.0182 (5)	−0.0004 (5)	0.0040 (4)	−0.0016 (5)
C11	0.0149 (5)	0.0167 (7)	0.0263 (6)	0.0011 (5)	0.0030 (5)	−0.0016 (5)
C12	0.0159 (5)	0.0193 (7)	0.0303 (7)	0.0011 (5)	0.0102 (5)	−0.0051 (5)
C13	0.0190 (5)	0.0180 (7)	0.0237 (6)	−0.0003 (5)	0.0118 (5)	−0.0035 (5)
C14	0.0239 (6)	0.0262 (8)	0.0172 (6)	0.0030 (5)	0.0121 (5)	0.0011 (5)

O1—N3	1.2259 (13)	C5—C6	1.3710 (17)
O2—N3	1.2424 (14)	C5—H5A	0.9300
O3—N4	1.2309 (14)	C6—H6A	0.9300
O4—N4	1.2332 (13)	C7—C8	1.4807 (17)
O5—N5	1.2220 (14)	C7—C14	1.5051 (16)
O6—N5	1.2284 (13)	C8—C13	1.4029 (16)
N1—C1	1.3535 (15)	C8—C9	1.4037 (16)
N1—N2	1.3672 (14)	C9—C10	1.3824 (17)
N1—H1	0.8766	C10—C11	1.3909 (18)
N2—C7	1.2909 (15)	C10—H10A	0.9300
N3—C2	1.4539 (14)	C11—C12	1.3849 (19)
N4—C4	1.4521 (15)	C11—H11A	0.9300
N5—C9	1.4812 (15)	C12—C13	1.3874 (18)
C1—C6	1.4210 (16)	C12—H12A	0.9300
C1—C2	1.4224 (16)	C13—H13A	0.9300
C2—C3	1.3835 (16)	C14—H14A	0.9600
C3—C4	1.3744 (16)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C4—C5	1.4014 (16)
C1—N1—N2	120.26 (10)	C5—C6—H6A	119.4
C1—N1—H1	118.2	C1—C6—H6A	119.4
N2—N1—H1	121.0	N2—C7—C8	116.26 (10)
C7—N2—N1	115.88 (10)	N2—C7—C14	123.38 (11)
O1—N3—O2	122.46 (10)	C8—C7—C14	120.34 (10)
O1—N3—C2	118.58 (10)	C13—C8—C9	115.60 (11)
O2—N3—C2	118.96 (10)	C13—C8—C7	120.47 (11)
O3—N4—O4	123.16 (10)	C9—C8—C7	123.89 (11)
O3—N4—C4	119.00 (10)	C10—C9—C8	123.37 (11)
O4—N4—C4	117.84 (10)	C10—C9—N5	114.72 (10)
O5—N5—O6	124.63 (10)	C8—C9—N5	121.88 (10)
O5—N5—C9	117.57 (10)	C9—C10—C11	119.14 (12)
O6—N5—C9	117.73 (10)	C9—C10—H10A	120.4
N1—C1—C6	121.03 (11)	C11—C10—H10A	120.4
N1—C1—C2	121.97 (10)	C12—C11—C10	119.46 (12)
C6—C1—C2	117.01 (11)	C12—C11—H11A	120.3
C3—C2—C1	121.72 (10)	C10—C11—H11A	120.3
C3—C2—N3	116.05 (10)	C11—C12—C13	120.47 (12)
C1—C2—N3	122.23 (10)	C11—C12—H12A	119.8
C4—C3—C2	118.92 (11)	C13—C12—H12A	119.8
C4—C3—H3A	120.5	C12—C13—C8	121.95 (12)
C2—C3—H3A	120.5	C12—C13—H13A	119.0
C3—C4—C5	121.71 (11)	C8—C13—H13A	119.0
C3—C4—N4	118.41 (10)	C7—C14—H14A	109.5
C5—C4—N4	119.88 (10)	C7—C14—H14B	109.5
C6—C5—C4	119.37 (11)	H14A—C14—H14B	109.5
C6—C5—H5A	120.3	C7—C14—H14C	109.5
C4—C5—H5A	120.3	H14A—C14—H14C	109.5
C5—C6—C1	121.27 (11)	H14B—C14—H14C	109.5
C1—N1—N2—C7	172.81 (11)	C2—C1—C6—C5	0.48 (19)
N2—N1—C1—C6	−4.25 (18)	N1—N2—C7—C8	177.22 (10)
N2—N1—C1—C2	176.20 (11)	N1—N2—C7—C14	−1.52 (18)
N1—C1—C2—C3	179.52 (11)	N2—C7—C8—C13	−169.40 (12)
C6—C1—C2—C3	−0.04 (18)	C14—C7—C8—C13	9.39 (18)
N1—C1—C2—N3	−0.93 (19)	N2—C7—C8—C9	8.14 (18)
C6—C1—C2—N3	179.51 (11)	C14—C7—C8—C9	−173.07 (12)
O1—N3—C2—C3	7.08 (17)	C13—C8—C9—C10	0.25 (18)
O2—N3—C2—C3	−172.76 (11)	C7—C8—C9—C10	−177.40 (12)
O1—N3—C2—C1	−172.51 (12)	C13—C8—C9—N5	−177.90 (11)
O2—N3—C2—C1	7.65 (18)	C7—C8—C9—N5	4.45 (18)
C1—C2—C3—C4	−0.68 (19)	O5—N5—C9—C10	−96.72 (13)
N3—C2—C3—C4	179.74 (11)	O6—N5—C9—C10	80.43 (13)
C2—C3—C4—C5	1.00 (19)	O5—N5—C9—C8	81.58 (14)
C2—C3—C4—N4	−178.99 (11)	O6—N5—C9—C8	−101.27 (13)
O3—N4—C4—C3	−0.47 (18)	C8—C9—C10—C11	−0.28 (19)
O4—N4—C4—C3	179.19 (11)	N5—C9—C10—C11	177.99 (11)
O3—N4—C4—C5	179.54 (12)	C9—C10—C11—C12	−0.39 (19)
O4—N4—C4—C5	−0.81 (17)	C10—C11—C12—C13	1.1 (2)
C3—C4—C5—C6	−0.6 (2)	C11—C12—C13—C8	−1.1 (2)
N4—C4—C5—C6	179.41 (12)	C9—C8—C13—C12	0.45 (18)
C4—C5—C6—C1	−0.2 (2)	C7—C8—C13—C12	178.18 (12)
N1—C1—C6—C5	−179.09 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.88	1.94	2.6026 (13)	131
C10—H10A···O4i	0.93	2.42	3.2313 (16)	146
C12—H12A···O4ii	0.93	2.55	3.4353 (18)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.88	1.94	2.6026 (13)	131
C10—H10A⋯O4i	0.93	2.42	3.2313 (16)	146
C12—H12A⋯O4ii	0.93	2.55	3.4353 (18)	159

Symmetry codes: (i) ; (ii) .