(E)-4-Nitro-N'-(3-nitro-benzyl-idene)benzohydrazide.

The title compound, C(14)H(10)N(4)O(5), has an E conformation with respect to the C=N bond. The dihedral angle between the benzene rings is 2.41 (14)°. In the crystal, mol-ecules are linked through N-H⋯O hydrogen bonds to form chains along the c axis. C-H⋯O inter-actions are also present, linking the chains to form a three-dimensional network.

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶). For the crystal structures of similar compounds, reported on by the author, see: Li (2011a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C14H10N4O5

M = 314.26

Monoclinic,

a = 11.856 (2) Å

b = 14.116 (3) Å

c = 8.6263 (19) Å

β = 95.193 (2)°

V = 1437.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.987

10319 measured reflections

2671 independent reflections

1288 reflections with I > 2σ(I)

R int = 0.104

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.123

S = 0.84

2671 reflections

211 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAIn class="Chemical">NT; 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004540/su2375sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004540/su2375Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004540/su2375Isup3.cml

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

C14H10N4O5	F(000) = 648
Mr = 314.26	Dx = 1.452 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 979 reflections
a = 11.856 (2) Å	θ = 2.3–26.3°
b = 14.116 (3) Å	µ = 0.11 mm−1
c = 8.6263 (19) Å	T = 298 K
β = 95.193 (2)°	Block, yellow
V = 1437.8 (5) Å3	0.17 × 0.13 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2671 independent reflections
Radiation source: fine-focus sealed tube	1288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.104
ω scans	θmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.981, Tmax = 0.987	k = −17→16
10319 measured reflections	l = −10→10

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 0.84	w = 1/[σ2(Fo2) + (0.0424P)2] where P = (Fo2 + 2Fc2)/3
2671 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.1287 (3)	1.33204 (17)	0.1686 (3)	0.1354 (15)
O2	0.2448 (3)	1.26884 (18)	0.0245 (4)	0.1188 (15)
O3	0.23263 (15)	0.65945 (12)	0.1876 (2)	0.0537 (7)
O4	0.4769 (3)	0.3590 (2)	−0.3204 (4)	0.1556 (18)
O5	0.5842 (3)	0.4737 (2)	−0.3733 (3)	0.1211 (14)
N1	0.17622 (18)	0.83659 (16)	0.0848 (2)	0.0491 (8)
N2	0.22711 (19)	0.76953 (16)	−0.0036 (2)	0.0483 (9)
N3	0.1702 (3)	1.2632 (2)	0.1105 (4)	0.0899 (16)
N4	0.5047 (3)	0.4393 (3)	−0.3104 (4)	0.0936 (16)
C1	0.1348 (2)	1.00191 (19)	0.1080 (3)	0.0425 (10)
C2	0.1696 (2)	1.0919 (2)	0.0706 (3)	0.0522 (11)
C3	0.1282 (3)	1.1686 (2)	0.1461 (4)	0.0581 (12)
C4	0.0505 (3)	1.1592 (2)	0.2540 (4)	0.0726 (14)
C5	0.0174 (3)	1.0690 (2)	0.2908 (4)	0.0689 (12)
C6	0.0592 (2)	0.9917 (2)	0.2202 (3)	0.0544 (11)
C7	0.1814 (2)	0.9203 (2)	0.0303 (3)	0.0486 (10)
C8	0.2553 (2)	0.68447 (18)	0.0579 (3)	0.0405 (10)
C9	0.3200 (2)	0.62217 (18)	−0.0417 (3)	0.0387 (9)
C10	0.3076 (2)	0.52468 (18)	−0.0295 (3)	0.0478 (10)
C11	0.3684 (3)	0.4655 (2)	−0.1197 (4)	0.0605 (11)
C12	0.4412 (3)	0.5048 (2)	−0.2157 (3)	0.0608 (11)
C13	0.4570 (2)	0.5997 (2)	−0.2249 (3)	0.0623 (12)
C14	0.3961 (2)	0.6581 (2)	−0.1383 (3)	0.0524 (11)
H2	0.22020	1.10040	−0.00440	0.0630*
H2A	0.245 (2)	0.7813 (19)	−0.1021 (16)	0.0800*
H4	0.02120	1.21200	0.30070	0.0870*
H5	−0.03420	1.06070	0.36470	0.0820*
H6	0.03660	0.93130	0.24770	0.0650*
H7	0.21570	0.92980	−0.06130	0.0580*
H10	0.25910	0.49930	0.03850	0.0570*
H11	0.35970	0.40020	−0.11490	0.0720*
H13	0.50850	0.62460	−0.28920	0.0750*
H14	0.40610	0.72330	−0.14440	0.0630*

	U11	U22	U33	U12	U13	U23
O1	0.204 (3)	0.0522 (16)	0.154 (3)	0.0280 (19)	0.039 (2)	−0.0131 (18)
O2	0.128 (3)	0.0639 (18)	0.169 (3)	−0.0092 (17)	0.039 (2)	0.0148 (18)
O3	0.0739 (14)	0.0488 (12)	0.0407 (11)	−0.0012 (10)	0.0178 (10)	0.0052 (10)
O4	0.157 (3)	0.110 (2)	0.196 (4)	0.058 (2)	−0.004 (2)	−0.077 (3)
O5	0.108 (2)	0.174 (3)	0.083 (2)	0.079 (2)	0.0178 (17)	−0.0014 (19)
N1	0.0579 (15)	0.0459 (15)	0.0454 (14)	0.0112 (12)	0.0145 (12)	−0.0004 (12)
N2	0.0655 (17)	0.0451 (14)	0.0371 (14)	0.0116 (12)	0.0198 (12)	0.0010 (12)
N3	0.116 (3)	0.051 (2)	0.101 (3)	0.012 (2)	0.000 (2)	0.0029 (19)
N4	0.080 (3)	0.125 (3)	0.072 (2)	0.054 (3)	−0.0140 (19)	−0.019 (2)
C1	0.0389 (16)	0.0469 (18)	0.0411 (16)	0.0061 (14)	0.0011 (13)	−0.0036 (14)
C2	0.0483 (19)	0.0519 (19)	0.0563 (19)	0.0063 (15)	0.0035 (15)	0.0006 (15)
C3	0.067 (2)	0.045 (2)	0.061 (2)	0.0126 (17)	−0.0010 (17)	−0.0018 (16)
C4	0.082 (3)	0.062 (2)	0.073 (2)	0.022 (2)	0.002 (2)	−0.0110 (19)
C5	0.061 (2)	0.079 (2)	0.068 (2)	0.022 (2)	0.0138 (17)	−0.005 (2)
C6	0.0494 (18)	0.058 (2)	0.0562 (19)	0.0044 (15)	0.0064 (15)	−0.0017 (16)
C7	0.0488 (18)	0.0550 (19)	0.0426 (17)	0.0011 (15)	0.0078 (14)	−0.0057 (15)
C8	0.0452 (17)	0.0394 (17)	0.0374 (16)	−0.0084 (13)	0.0061 (13)	0.0025 (13)
C9	0.0395 (16)	0.0402 (16)	0.0365 (15)	0.0007 (13)	0.0038 (13)	0.0013 (13)
C10	0.0509 (18)	0.0423 (17)	0.0494 (18)	−0.0025 (15)	0.0000 (14)	0.0004 (14)
C11	0.066 (2)	0.0439 (18)	0.067 (2)	0.0093 (17)	−0.0183 (18)	−0.0127 (17)
C12	0.059 (2)	0.074 (2)	0.0479 (19)	0.0325 (19)	−0.0027 (16)	−0.0147 (18)
C13	0.059 (2)	0.076 (2)	0.054 (2)	0.0204 (18)	0.0167 (17)	0.0064 (18)
C14	0.0540 (19)	0.0489 (18)	0.0566 (19)	0.0053 (15)	0.0176 (15)	0.0063 (15)

O1—N3	1.218 (4)	C5—C6	1.365 (4)
O2—N3	1.207 (5)	C8—C9	1.490 (4)
O3—C8	1.226 (3)	C9—C14	1.379 (4)
O4—N4	1.181 (5)	C9—C10	1.389 (4)
O5—N4	1.229 (5)	C10—C11	1.387 (4)
N1—N2	1.387 (3)	C11—C12	1.367 (5)
N1—C7	1.275 (4)	C12—C13	1.356 (4)
N2—C8	1.343 (3)	C13—C14	1.363 (4)
N3—C3	1.467 (4)	C2—H2	0.9300
N4—C12	1.483 (5)	C4—H4	0.9300
N2—H2A	0.910 (16)	C5—H5	0.9300
C1—C6	1.385 (4)	C6—H6	0.9300
C1—C7	1.466 (4)	C7—H7	0.9300
C1—C2	1.383 (4)	C10—H10	0.9300
C2—C3	1.377 (4)	C11—H11	0.9300
C3—C4	1.374 (5)	C13—H13	0.9300
C4—C5	1.378 (4)	C14—H14	0.9300
N2—N1—C7	113.1 (2)	C8—C9—C14	122.0 (2)
N1—N2—C8	119.87 (19)	C9—C10—C11	119.4 (2)
O1—N3—O2	123.1 (3)	C10—C11—C12	119.0 (3)
O1—N3—C3	118.9 (3)	N4—C12—C13	120.3 (3)
O2—N3—C3	118.0 (3)	N4—C12—C11	117.4 (3)
O4—N4—O5	124.5 (4)	C11—C12—C13	122.3 (3)
O4—N4—C12	119.1 (3)	C12—C13—C14	118.9 (3)
O5—N4—C12	116.4 (4)	C9—C14—C13	121.1 (3)
C8—N2—H2A	117.5 (17)	C1—C2—H2	120.00
N1—N2—H2A	122.6 (17)	C3—C2—H2	121.00
C2—C1—C7	118.9 (2)	C3—C4—H4	121.00
C2—C1—C6	119.0 (2)	C5—C4—H4	121.00
C6—C1—C7	122.2 (2)	C4—C5—H5	120.00
C1—C2—C3	119.0 (2)	C6—C5—H5	120.00
N3—C3—C4	119.4 (3)	C1—C6—H6	120.00
N3—C3—C2	118.3 (3)	C5—C6—H6	120.00
C2—C3—C4	122.3 (3)	N1—C7—H7	119.00
C3—C4—C5	117.9 (3)	C1—C7—H7	119.00
C4—C5—C6	120.9 (3)	C9—C10—H10	120.00
C1—C6—C5	120.9 (3)	C11—C10—H10	120.00
N1—C7—C1	121.8 (2)	C10—C11—H11	120.00
O3—C8—C9	121.5 (2)	C12—C11—H11	121.00
N2—C8—C9	115.0 (2)	C12—C13—H13	121.00
O3—C8—N2	123.4 (2)	C14—C13—H13	120.00
C10—C9—C14	119.3 (2)	C9—C14—H14	119.00
C8—C9—C10	118.5 (2)	C13—C14—H14	119.00
C7—N1—N2—C8	162.4 (2)	C1—C2—C3—C4	−2.2 (5)
N2—N1—C7—C1	−178.7 (2)	N3—C3—C4—C5	−176.6 (3)
N1—N2—C8—O3	4.4 (4)	C2—C3—C4—C5	2.6 (5)
N1—N2—C8—C9	−173.9 (2)	C3—C4—C5—C6	−1.1 (5)
O1—N3—C3—C2	175.1 (3)	C4—C5—C6—C1	−0.9 (5)
O1—N3—C3—C4	−5.6 (5)	O3—C8—C9—C10	31.6 (4)
O2—N3—C3—C2	−4.9 (5)	O3—C8—C9—C14	−144.7 (3)
O2—N3—C3—C4	174.3 (4)	N2—C8—C9—C10	−150.0 (2)
O4—N4—C12—C11	12.8 (5)	N2—C8—C9—C14	33.7 (3)
O4—N4—C12—C13	−167.8 (3)	C8—C9—C10—C11	−179.1 (3)
O5—N4—C12—C11	−166.9 (3)	C14—C9—C10—C11	−2.7 (4)
O5—N4—C12—C13	12.5 (5)	C8—C9—C14—C13	178.0 (2)
C6—C1—C2—C3	0.1 (4)	C10—C9—C14—C13	1.8 (4)
C7—C1—C2—C3	−178.4 (3)	C9—C10—C11—C12	1.6 (4)
C2—C1—C6—C5	1.4 (4)	C10—C11—C12—N4	−180.0 (3)
C7—C1—C6—C5	179.9 (3)	C10—C11—C12—C13	0.7 (5)
C2—C1—C7—N1	162.1 (2)	N4—C12—C13—C14	179.0 (3)
C6—C1—C7—N1	−16.4 (4)	C11—C12—C13—C14	−1.7 (4)
C1—C2—C3—N3	177.1 (3)	C12—C13—C14—C9	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.91 (2)	1.99 (2)	2.853 (3)	158 (2)
C6—H6···O1ii	0.93	2.57	3.369 (4)	145
C7—H7···O5iii	0.93	2.56	3.287 (4)	135
C7—H7···O3i	0.93	2.53	3.271 (3)	137
C14—H14···O4iii	0.93	2.40	3.246 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.91 (2)	1.99 (2)	2.853 (3)	158 (2)
C6—H6⋯O1ii	0.93	2.57	3.369 (4)	145
C7—H7⋯O5iii	0.93	2.56	3.287 (4)	135
C7—H7⋯O3i	0.93	2.53	3.271 (3)	137
C14—H14⋯O4iii	0.93	2.40	3.246 (4)	151

Symmetry codes: (i) ; (ii) ; (iii) .