(1E,2E)-1,2-Bis[1-(3-nitro-phen-yl)ethyl-idene]hydrazine.

The asymmetric unit of the title compound, C(16)H(14)N(4)O(4), contains one half-mol-ecule of (nitro-phen-yl)ethanimine and the complete mol-ecule is generated by a crystallographic inversion centre. The mol-ecule has an E conformation with respect to each C=N double bond. The central C=N-N=C plane is twisted from the benzene rings with a dihedral angle of 24.76 (11)°. In the crystal, C-H⋯O inter-actions link the molecules to form sheets that lie parallel to (10-4).

Related literature

For the biological acivity of hydrazones, see: Khanmohammadi et al. (2008 ▶); Luboch et al. (2009 ▶). For related structures, see: Chantrapromma et al. (2011 ▶); Fun, Jansrisewangwong et al. (2011 ▶); Fun, Nilwanna et al. (2011 ▶); Jansrisewangwong et al. (2010 ▶); Nilwanna et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14N4O4

M = 326.31

Monoclinic,

a = 3.9296 (3) Å

b = 7.4448 (5) Å

c = 26.3979 (19) Å

β = 94.022 (1)°

V = 770.37 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.34 × 0.17 × 0.10 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.966, T max = 0.990

15392 measured reflections

2254 independent reflections

1686 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.146

S = 1.06

2254 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536812004722/is5067sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004722/is5067Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004722/is5067Isup3.cml

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

C16H14N4O4	F(000) = 340
Mr = 326.31	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4585 reflections
a = 3.9296 (3) Å	θ = 2.8–28.3°
b = 7.4448 (5) Å	µ = 0.10 mm−1
c = 26.3979 (19) Å	T = 296 K
β = 94.022 (1)°	Block, yellow
V = 770.37 (10) Å3	0.34 × 0.17 × 0.10 mm
Z = 2

Bruker APEX DUO CCD area-detector diffractometer	2254 independent reflections
Radiation source: fine-focus sealed tube	1686 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 30.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.966, Tmax = 0.990	k = −10→10
15392 measured reflections	l = −37→37

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.069P)2 + 0.1466P] where P = (Fo2 + 2Fc2)/3
2254 reflections	(Δ/σ)max < 0.001
110 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.9642 (5)	0.1248 (2)	0.20045 (5)	0.1005 (6)
O2	0.8102 (4)	0.06399 (18)	0.12349 (5)	0.0867 (5)
N1	0.0796 (3)	0.47453 (16)	0.02358 (4)	0.0461 (3)
N2	0.8220 (3)	0.16404 (18)	0.15972 (5)	0.0572 (3)
C1	0.3995 (4)	0.6788 (2)	0.14058 (5)	0.0507 (3)
H1A	0.3117	0.7942	0.1362	0.061*
C2	0.5585 (4)	0.6293 (2)	0.18705 (6)	0.0583 (4)
H2A	0.5726	0.7113	0.2137	0.070*
C3	0.6956 (4)	0.4607 (2)	0.19421 (5)	0.0525 (4)
H3A	0.8039	0.4272	0.2252	0.063*
C4	0.6669 (3)	0.34261 (18)	0.15379 (5)	0.0429 (3)
C5	0.5072 (3)	0.38640 (17)	0.10740 (4)	0.0400 (3)
H5A	0.4914	0.3029	0.0811	0.048*
C6	0.3697 (3)	0.55758 (17)	0.10032 (4)	0.0390 (3)
C7	0.1991 (3)	0.60690 (18)	0.05020 (5)	0.0399 (3)
C8	0.1829 (5)	0.7991 (2)	0.03461 (6)	0.0643 (4)
H8A	0.1410	0.8068	−0.0016	0.096*
H8B	0.3956	0.8567	0.0447	0.096*
H8C	0.0016	0.8578	0.0507	0.096*

	U11	U22	U33	U12	U13	U23
O1	0.1420 (14)	0.0814 (10)	0.0708 (9)	0.0246 (9)	−0.0438 (9)	0.0216 (7)
O2	0.1242 (12)	0.0551 (7)	0.0763 (9)	0.0281 (7)	−0.0242 (8)	−0.0045 (6)
N1	0.0550 (6)	0.0460 (6)	0.0357 (5)	0.0002 (5)	−0.0080 (4)	0.0071 (4)
N2	0.0638 (8)	0.0518 (7)	0.0535 (7)	0.0030 (6)	−0.0133 (6)	0.0126 (6)
C1	0.0561 (8)	0.0465 (7)	0.0488 (8)	0.0046 (6)	−0.0020 (6)	−0.0061 (6)
C2	0.0696 (10)	0.0617 (9)	0.0424 (7)	−0.0022 (7)	−0.0053 (6)	−0.0130 (6)
C3	0.0576 (8)	0.0632 (9)	0.0350 (6)	−0.0071 (7)	−0.0088 (5)	0.0015 (6)
C4	0.0440 (6)	0.0450 (7)	0.0388 (6)	−0.0030 (5)	−0.0044 (5)	0.0058 (5)
C5	0.0430 (6)	0.0426 (7)	0.0338 (6)	−0.0013 (5)	−0.0024 (4)	0.0006 (5)
C6	0.0383 (6)	0.0425 (6)	0.0357 (6)	0.0002 (5)	−0.0007 (4)	0.0015 (5)
C7	0.0391 (6)	0.0426 (7)	0.0376 (6)	0.0045 (5)	0.0003 (4)	0.0042 (5)
C8	0.0847 (11)	0.0450 (8)	0.0600 (9)	0.0046 (8)	−0.0171 (8)	0.0064 (7)

O1—N2	1.2121 (16)	C3—C4	1.3808 (19)
O2—N2	1.2105 (19)	C3—H3A	0.9300
N1—C7	1.2803 (17)	C4—C5	1.3756 (17)
N1—N1i	1.406 (2)	C5—C6	1.3916 (18)
N2—C4	1.4663 (19)	C5—H5A	0.9300
C1—C2	1.387 (2)	C6—C7	1.4867 (17)
C1—C6	1.3930 (19)	C7—C8	1.489 (2)
C1—H1A	0.9300	C8—H8A	0.9600
C2—C3	1.374 (2)	C8—H8B	0.9600
C2—H2A	0.9300	C8—H8C	0.9600
C7—N1—N1i	113.69 (14)	C4—C5—C6	119.02 (12)
O2—N2—O1	122.84 (15)	C4—C5—H5A	120.5
O2—N2—C4	118.75 (12)	C6—C5—H5A	120.5
O1—N2—C4	118.38 (14)	C5—C6—C1	118.67 (11)
C2—C1—C6	120.76 (14)	C5—C6—C7	119.49 (11)
C2—C1—H1A	119.6	C1—C6—C7	121.84 (12)
C6—C1—H1A	119.6	N1—C7—C6	115.05 (11)
C3—C2—C1	120.81 (14)	N1—C7—C8	125.53 (12)
C3—C2—H2A	119.6	C6—C7—C8	119.41 (12)
C1—C2—H2A	119.6	C7—C8—H8A	109.5
C2—C3—C4	117.74 (12)	C7—C8—H8B	109.5
C2—C3—H3A	121.1	H8A—C8—H8B	109.5
C4—C3—H3A	121.1	C7—C8—H8C	109.5
C5—C4—C3	122.99 (13)	H8A—C8—H8C	109.5
C5—C4—N2	118.04 (12)	H8B—C8—H8C	109.5
C3—C4—N2	118.94 (12)
C6—C1—C2—C3	1.1 (2)	C4—C5—C6—C1	0.12 (19)
C1—C2—C3—C4	−0.5 (2)	C4—C5—C6—C7	179.49 (11)
C2—C3—C4—C5	−0.3 (2)	C2—C1—C6—C5	−0.9 (2)
C2—C3—C4—N2	177.71 (14)	C2—C1—C6—C7	179.72 (13)
O2—N2—C4—C5	1.6 (2)	N1i—N1—C7—C6	−179.90 (13)
O1—N2—C4—C5	179.73 (15)	N1i—N1—C7—C8	−0.7 (2)
O2—N2—C4—C3	−176.58 (16)	C5—C6—C7—N1	24.84 (17)
O1—N2—C4—C3	1.6 (2)	C1—C6—C7—N1	−155.80 (13)
C3—C4—C5—C6	0.5 (2)	C5—C6—C7—C8	−154.43 (14)
N2—C4—C5—C6	−177.55 (11)	C1—C6—C7—C8	24.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ii	0.93	2.57	3.239 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1i	0.93	2.57	3.239 (2)	129

Symmetry code: (i) .