1,2-Bis(4-nitro-benzo-yl)hydrazine.

The title mol-ecule, C(14)H(10)N(4)O(6), crystallizes with one half-mol-ecule in the asymmetric unit; the mid-point of the N-N bond lies on an inversion centre. The nitro and amide groups are twisted with respect to the benzene ring, making dihedral angles of 14.6 (5) and 31.1 (5)°, respectively. In the crystal structure, mol-ecules are linked through N-H⋯O hydrogen bonding between the imino and carbonyl groups.

Related literature

For the biological activity of hydrazides, see: Cui et al. (2007 ▶); Li & Ban (2009 ▶). For related structures, see: Shang et al. (2005a ▶,b ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C14H10N4O6

M = 330.26

Monoclinic,

a = 4.7947 (6) Å

b = 9.8750 (11) Å

c = 14.9094 (17) Å

β = 99.05 (3)°

V = 697.13 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.975, T max = 0.988

1364 measured reflections

1364 independent reflections

673 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.220

S = 1.10

1364 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903181X/xu2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903181X/xu2587Isup2.hkl

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

C14H10N4O6	F(000) = 340
Mr = 330.26	Dx = 1.573 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 4.7947 (6) Å	θ = 8–12°
b = 9.8750 (11) Å	µ = 0.13 mm−1
c = 14.9094 (17) Å	T = 293 K
β = 99.05 (3)°	Block, colorless
V = 697.13 (14) Å3	0.20 × 0.10 × 0.10 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	673 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0000
graphite	θmax = 26.0°, θmin = 2.5°
ω/2θ scans	h = −5→5
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
Tmin = 0.975, Tmax = 0.988	l = 0→18
1364 measured reflections	3 standard reflections every 200 reflections
1364 independent reflections	intensity decay: none

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.220	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0632P)2 + 0.1296P] where P = (Fo2 + 2Fc2)/3
1364 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.15 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
O1	0.5717 (7)	−0.0146 (4)	0.4016 (2)	0.0940 (11)
O2	0.8216 (9)	0.1386 (5)	−0.0278 (3)	0.1227 (16)
O3	1.2216 (11)	0.2315 (5)	0.0270 (3)	0.1219 (15)
N1	1.0280 (8)	0.0187 (4)	0.4580 (2)	0.0842 (12)
H1A	1.1951	0.0419	0.4498	0.101*
N2	1.0017 (12)	0.1715 (5)	0.0358 (3)	0.0949 (13)
C1	0.8102 (10)	0.0176 (5)	0.3890 (3)	0.0794 (12)
C2	0.8783 (10)	0.0610 (5)	0.2994 (3)	0.0775 (12)
C3	0.7163 (12)	0.0022 (6)	0.2224 (4)	0.1007 (16)
H3A	0.5823	−0.0633	0.2297	0.121*
C4	0.7531 (11)	0.0399 (6)	0.1371 (3)	0.0920 (15)
H4A	0.6379	0.0047	0.0865	0.110*
C5	0.9622 (12)	0.1304 (6)	0.1272 (3)	0.0897 (14)
C6	1.1218 (12)	0.1918 (5)	0.2030 (4)	0.0926 (15)
H6A	1.2522	0.2587	0.1952	0.111*
C7	1.0864 (12)	0.1540 (5)	0.2868 (3)	0.0939 (15)
H7A	1.2021	0.1903	0.3370	0.113*

	U11	U22	U33	U12	U13	U23
O1	0.087 (2)	0.124 (3)	0.0660 (19)	−0.004 (2)	−0.0060 (16)	0.0027 (19)
O2	0.140 (3)	0.145 (4)	0.070 (2)	0.015 (3)	−0.024 (2)	0.009 (3)
O3	0.156 (4)	0.117 (3)	0.090 (3)	−0.013 (3)	0.010 (3)	0.015 (2)
N1	0.077 (2)	0.102 (3)	0.065 (2)	−0.004 (2)	−0.0141 (18)	0.012 (2)
N2	0.117 (3)	0.085 (3)	0.082 (3)	0.014 (3)	0.009 (3)	0.014 (2)
C1	0.086 (3)	0.076 (3)	0.070 (3)	0.000 (2)	−0.007 (2)	0.003 (2)
C2	0.081 (3)	0.079 (3)	0.064 (2)	0.006 (2)	−0.017 (2)	0.005 (2)
C3	0.109 (4)	0.098 (4)	0.080 (3)	−0.017 (3)	−0.029 (3)	0.002 (3)
C4	0.099 (3)	0.102 (4)	0.066 (3)	−0.008 (3)	−0.012 (3)	0.001 (3)
C5	0.113 (4)	0.079 (3)	0.070 (3)	0.017 (3)	−0.009 (3)	0.011 (3)
C6	0.114 (4)	0.075 (3)	0.079 (3)	−0.008 (3)	−0.017 (3)	0.005 (3)
C7	0.112 (4)	0.079 (3)	0.075 (3)	−0.005 (3)	−0.035 (3)	0.003 (3)

O1—C1	1.229 (5)	C2—C3	1.407 (7)
O2—N2	1.221 (6)	C3—C4	1.362 (7)
O3—N2	1.234 (5)	C3—H3A	0.9300
N1—C1	1.346 (6)	C4—C5	1.368 (7)
N1—N1i	1.372 (7)	C4—H4A	0.9300
N1—H1A	0.8600	C5—C6	1.400 (7)
N2—C5	1.462 (6)	C6—C7	1.340 (7)
C1—C2	1.488 (6)	C6—H6A	0.9300
C2—C7	1.390 (7)	C7—H7A	0.9300
C1—N1—N1i	117.1 (5)	C2—C3—H3A	119.6
C1—N1—H1A	121.5	C3—C4—C5	119.0 (5)
N1i—N1—H1A	121.5	C3—C4—H4A	120.5
O2—N2—O3	123.8 (5)	C5—C4—H4A	120.5
O2—N2—C5	118.0 (5)	C4—C5—C6	120.8 (5)
O3—N2—C5	118.1 (5)	C4—C5—N2	119.1 (5)
O1—C1—N1	121.0 (4)	C6—C5—N2	119.8 (5)
O1—C1—C2	123.5 (4)	C7—C6—C5	119.9 (5)
N1—C1—C2	115.5 (4)	C7—C6—H6A	120.0
C7—C2—C3	118.6 (5)	C5—C6—H6A	120.0
C7—C2—C1	125.1 (5)	C6—C7—C2	120.6 (5)
C3—C2—C1	116.3 (5)	C6—C7—H7A	119.7
C4—C3—C2	120.9 (5)	C2—C7—H7A	119.7
C4—C3—H3A	119.6
N1i—N1—C1—O1	0.7 (8)	C3—C4—C5—N2	−179.8 (5)
N1i—N1—C1—C2	179.0 (5)	O2—N2—C5—C4	10.3 (7)
O1—C1—C2—C7	148.0 (5)	O3—N2—C5—C4	−166.2 (5)
N1—C1—C2—C7	−30.3 (7)	O2—N2—C5—C6	−164.5 (5)
O1—C1—C2—C3	−31.9 (7)	O3—N2—C5—C6	19.0 (7)
N1—C1—C2—C3	149.8 (5)	C4—C5—C6—C7	5.5 (8)
C7—C2—C3—C4	−3.0 (8)	N2—C5—C6—C7	−179.8 (5)
C1—C2—C3—C4	176.9 (5)	C5—C6—C7—C2	−4.6 (8)
C2—C3—C4—C5	3.8 (9)	C3—C2—C7—C6	3.4 (8)
C3—C4—C5—C6	−5.0 (8)	C1—C2—C7—C6	−176.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ii	0.86	2.12	2.881 (5)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.12	2.881 (5)	147

Symmetry code: (i) .