N'-(2,4-Dinitro-phen-yl)acetohydrazide.

In the title compound, C(8)H(8)N(4)O(5), the nitro groups ortho and para to the hydrazone group are twisted by 10.0 (2) and 3.6 (2)°, respectively, relative to the aromatic ring. The structure exhibits an intra-molecular N-H⋯O hydrogen bond between the hydrazide and ortho-nitro groups. There is a strong inter-molecular C=O⋯H-N hydrogen bond, giving rise to chains, and weaker ONO⋯NO(2) [2.944 (2) Å] and C-H⋯O-N inter-actions linking the mol-ecules into a three-dimensional network.

Related literature

For related literature, see: Domiano et al. (1984 ▶); Guo (2007 ▶); Li et al. (1988 ▶); Rudnicka & Osmialowska (1979 ▶); Sakamoto et al. (1993 ▶); Siddiqui et al. (2007 ▶); Zia-ur-Rehman et al. (2005 ▶, 2006 ▶).

Experimental

Crystal data

C8H8N4O5

M = 240.18

Orthorhombic,

a = 4.8585 (4) Å

b = 10.7703 (8) Å

c = 19.1059 (14) Å

V = 999.76 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 150 (2) K

0.57 × 0.09 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.927, T max = 0.992

11843 measured reflections

1794 independent reflections

1616 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.078

S = 1.03

1794 reflections

161 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019685/bt2733sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019685/bt2733Isup2.hkl

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

C8H8N4O5	F000 = 496
Mr = 240.18	Dx = 1.596 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3491 reflections
a = 4.8585 (4) Å	θ = 2.9–27.8º
b = 10.7703 (8) Å	µ = 0.14 mm−1
c = 19.1059 (14) Å	T = 150 (2) K
V = 999.76 (13) Å3	Lath, orange
Z = 4	0.57 × 0.09 × 0.06 mm

Bruker APEXII CCD diffractometer	1794 independent reflections
Radiation source: fine-focus sealed tube	1616 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 150(2) K	θmax = 30.6º
ω rotation with narrow frames scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	h = −6→6
Tmin = 0.927, Tmax = 0.992	k = −15→15
11843 measured reflections	l = −27→27

Refinement on F2	Secondary atom site location: all non-H atoms found by direct methods
Least-squares matrix: full	Hydrogen site location: geom except NH coords freely refined
R[F2 > 2σ(F2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0462P)2 + 0.078P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1794 reflections	Δρmax = 0.27 e Å−3
161 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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. 1255 Friedel pairs. Friedels merged.

	x	y	z	Uiso*/Ueq
C1	0.3396 (3)	0.64098 (13)	0.89834 (7)	0.0206 (3)
N1	0.1186 (2)	0.67553 (11)	0.94555 (6)	0.0239 (2)
O1	0.0352 (2)	0.78314 (10)	0.94499 (6)	0.0298 (2)
O2	0.0219 (2)	0.59512 (11)	0.98457 (6)	0.0349 (3)
C2	0.4679 (3)	0.73783 (13)	0.86286 (7)	0.0234 (3)
H2	0.4153	0.8215	0.8710	0.028*
C3	0.6722 (3)	0.70968 (14)	0.81593 (7)	0.0245 (3)
N2	0.8161 (3)	0.81093 (13)	0.78132 (7)	0.0323 (3)
O3	0.7483 (3)	0.91873 (12)	0.79517 (7)	0.0428 (3)
O4	1.0012 (3)	0.78354 (13)	0.73998 (7)	0.0462 (3)
C4	0.7508 (3)	0.58725 (15)	0.80240 (7)	0.0253 (3)
H4A	0.8903	0.5700	0.7689	0.030*
C5	0.6255 (3)	0.49242 (13)	0.83774 (7)	0.0231 (3)
H5	0.6791	0.4093	0.8283	0.028*
C6	0.4174 (3)	0.51517 (13)	0.88817 (7)	0.0200 (3)
N3	0.3089 (3)	0.42103 (11)	0.92557 (7)	0.0243 (3)
H3	0.172 (4)	0.4329 (16)	0.9508 (10)	0.029*
N4	0.3548 (3)	0.29805 (11)	0.90659 (7)	0.0222 (2)
H4	0.518 (4)	0.2710 (16)	0.9126 (10)	0.027*
C7	0.1401 (3)	0.21961 (13)	0.91490 (7)	0.0222 (3)
O5	−0.0894 (2)	0.25786 (10)	0.93114 (6)	0.0291 (2)
C8	0.2055 (4)	0.08501 (14)	0.90370 (9)	0.0310 (3)
H8A	0.1747	0.0392	0.9473	0.047*
H8B	0.3984	0.0764	0.8895	0.047*
H8C	0.0861	0.0515	0.8669	0.047*

	U11	U22	U33	U12	U13	U23
C1	0.0161 (6)	0.0247 (6)	0.0211 (6)	−0.0007 (5)	−0.0003 (5)	−0.0036 (5)
N1	0.0187 (5)	0.0254 (5)	0.0276 (6)	−0.0018 (5)	0.0007 (5)	−0.0083 (5)
O1	0.0243 (5)	0.0272 (5)	0.0380 (6)	0.0046 (4)	−0.0021 (5)	−0.0092 (4)
O2	0.0334 (6)	0.0304 (6)	0.0408 (6)	−0.0044 (5)	0.0178 (5)	−0.0053 (5)
C2	0.0218 (6)	0.0241 (6)	0.0242 (6)	−0.0029 (5)	−0.0050 (5)	0.0001 (5)
C3	0.0229 (6)	0.0303 (7)	0.0203 (6)	−0.0070 (6)	−0.0027 (5)	0.0046 (5)
N2	0.0323 (7)	0.0384 (7)	0.0262 (6)	−0.0125 (6)	−0.0069 (6)	0.0095 (5)
O3	0.0475 (8)	0.0320 (6)	0.0489 (7)	−0.0124 (6)	−0.0052 (6)	0.0114 (5)
O4	0.0430 (7)	0.0581 (8)	0.0374 (6)	−0.0177 (7)	0.0111 (6)	0.0105 (6)
C4	0.0203 (7)	0.0352 (7)	0.0203 (6)	−0.0025 (6)	0.0020 (5)	0.0001 (6)
C5	0.0205 (6)	0.0267 (6)	0.0221 (6)	0.0012 (5)	0.0029 (5)	−0.0024 (5)
C6	0.0161 (6)	0.0238 (6)	0.0200 (6)	−0.0007 (5)	−0.0006 (5)	−0.0014 (5)
N3	0.0210 (6)	0.0217 (5)	0.0301 (6)	0.0006 (5)	0.0084 (5)	−0.0019 (5)
N4	0.0154 (5)	0.0200 (5)	0.0312 (6)	0.0011 (4)	0.0006 (5)	−0.0004 (5)
C7	0.0182 (6)	0.0256 (6)	0.0228 (6)	−0.0011 (5)	−0.0022 (5)	0.0029 (5)
O5	0.0159 (5)	0.0339 (6)	0.0375 (6)	−0.0002 (4)	0.0012 (4)	0.0046 (5)
C8	0.0308 (8)	0.0235 (6)	0.0389 (8)	−0.0011 (6)	−0.0008 (7)	0.0019 (6)

C1—C2	1.3915 (19)	C5—C6	1.4178 (18)
C1—C6	1.4202 (19)	C5—H5	0.9500
C1—N1	1.4508 (18)	C6—N3	1.3477 (18)
N1—O1	1.2278 (16)	N3—N4	1.3913 (17)
N1—O2	1.2354 (16)	N3—H3	0.83 (2)
C2—C3	1.371 (2)	N4—C7	1.3519 (18)
C2—H2	0.9500	N4—H4	0.85 (2)
C3—C4	1.397 (2)	C7—O5	1.2282 (17)
C3—N2	1.4543 (19)	C7—C8	1.500 (2)
N2—O4	1.233 (2)	C8—H8A	0.9800
N2—O3	1.2355 (19)	C8—H8B	0.9800
C4—C5	1.367 (2)	C8—H8C	0.9800
C4—H4A	0.9500
C2—C1—C6	121.96 (13)	C6—C5—H5	119.2
C2—C1—N1	116.25 (12)	N3—C6—C5	120.61 (13)
C6—C1—N1	121.79 (12)	N3—C6—C1	122.76 (12)
O1—N1—O2	122.79 (12)	C5—C6—C1	116.59 (12)
O1—N1—C1	118.74 (12)	C6—N3—N4	121.01 (12)
O2—N1—C1	118.47 (12)	C6—N3—H3	120.3 (12)
C3—C2—C1	118.50 (13)	N4—N3—H3	115.2 (12)
C3—C2—H2	120.8	C7—N4—N3	116.14 (12)
C1—C2—H2	120.8	C7—N4—H4	119.2 (12)
C2—C3—C4	121.83 (13)	N3—N4—H4	116.0 (13)
C2—C3—N2	118.65 (14)	O5—C7—N4	121.37 (13)
C4—C3—N2	119.49 (13)	O5—C7—C8	123.55 (14)
O4—N2—O3	123.81 (14)	N4—C7—C8	115.07 (13)
O4—N2—C3	117.56 (14)	C7—C8—H8A	109.5
O3—N2—C3	118.63 (15)	C7—C8—H8B	109.5
C5—C4—C3	119.47 (13)	H8A—C8—H8B	109.5
C5—C4—H4A	120.3	C7—C8—H8C	109.5
C3—C4—H4A	120.3	H8A—C8—H8C	109.5
C4—C5—C6	121.60 (13)	H8B—C8—H8C	109.5
C4—C5—H5	119.2
C2—C1—N1—O1	9.02 (18)	N2—C3—C4—C5	176.53 (13)
C6—C1—N1—O1	−170.04 (13)	C3—C4—C5—C6	−0.2 (2)
C2—C1—N1—O2	−171.10 (12)	C4—C5—C6—N3	−175.76 (14)
C6—C1—N1—O2	9.84 (19)	C4—C5—C6—C1	2.1 (2)
C6—C1—C2—C3	1.1 (2)	C2—C1—C6—N3	175.25 (13)
N1—C1—C2—C3	−177.94 (12)	N1—C1—C6—N3	−5.7 (2)
C1—C2—C3—C4	0.9 (2)	C2—C1—C6—C5	−2.53 (19)
C1—C2—C3—N2	−177.00 (13)	N1—C1—C6—C5	176.47 (12)
C2—C3—N2—O4	179.13 (13)	C5—C6—N3—N4	−13.1 (2)
C4—C3—N2—O4	1.2 (2)	C1—C6—N3—N4	169.18 (13)
C2—C3—N2—O3	−0.3 (2)	C6—N3—N4—C7	−142.12 (14)
C4—C3—N2—O3	−178.27 (14)	N3—N4—C7—O5	7.5 (2)
C2—C3—C4—C5	−1.3 (2)	N3—N4—C7—C8	−171.84 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O2	0.83 (2)	2.001 (18)	2.5942 (16)	127.9 (16)
N4—H4···O5i	0.85 (2)	1.95 (2)	2.7748 (16)	164.0 (17)
C5—H5···O4ii	0.95	2.44	3.249 (2)	143
C8—H8A···O2iii	0.98	2.58	3.269 (2)	128
C8—H8C···O3iv	0.98	2.57	3.527 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O2	0.83 (2)	2.001 (18)	2.5942 (16)	127.9 (16)
N4—H4⋯O5i	0.85 (2)	1.95 (2)	2.7748 (16)	164.0 (17)
C5—H5⋯O4ii	0.95	2.44	3.249 (2)	143
C8—H8A⋯O2iii	0.98	2.58	3.269 (2)	128
C8—H8C⋯O3iv	0.98	2.57	3.527 (2)	165

Symmetry code: (i) ; (ii) ; (iii) ; (iv) .