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

The mol-ecule of the title compound, C(15)H(14)N(4)O(5), is in an E conformation with respect to the C=N double bond and the dihedral angle between the two benzene rings is 37.83 (7)°. The ethyl-idenehydrazine plane makes dihedral angles of 4.93 (9) and 42.38 (9)° with the two benzene rings. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions into chains along the c axis which are stacked along the b axis by aromatic π-π inter-actions with a centroid-centroid distance of 3.5927 (10) Å.

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 ▶); Jansrisewangwong et al. (2010 ▶); Nilwanna et al. (2011 ▶). For background to the biological activity of hydro­zones, see: Bendre et al. (1998 ▶); Cui et al. (2010 ▶); Gokce et al. (2009 ▶); Khan et al. (2007 ▶); Loncle et al. (2004 ▶); Wang et al. (2009 ▶).

Experimental

Crystal data

C15H14N4O5

M = 330.30

Monoclinic,

a = 33.105 (5) Å

b = 7.1288 (10) Å

c = 13.4964 (19) Å

β = 107.170 (2)°

V = 3043.2 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 297 K

0.35 × 0.33 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.962, T max = 0.977

11675 measured reflections

4013 independent reflections

2945 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.124

S = 1.04

4013 reflections

223 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 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/S1600536811045417/hb6478sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045417/hb6478Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045417/hb6478Isup3.cml

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

C15H14N4O5	F(000) = 1376
Mr = 330.30	Dx = 1.442 Mg m−3
Monoclinic, C2/c	Melting point = 462–463 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 33.105 (5) Å	Cell parameters from 4013 reflections
b = 7.1288 (10) Å	θ = 2.6–29.0°
c = 13.4964 (19) Å	µ = 0.11 mm−1
β = 107.170 (2)°	T = 297 K
V = 3043.2 (8) Å3	Block, orange
Z = 8	0.35 × 0.33 × 0.21 mm

Bruker APEXII CCD diffractometer	4013 independent reflections
Radiation source: sealed tube	2945 reflections with I > 2σ(I)
graphite	Rint = 0.019
φ and ω scans	θmax = 29.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −44→43
Tmin = 0.962, Tmax = 0.977	k = −7→9
11675 measured reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0564P)2 + 1.0718P] where P = (Fo2 + 2Fc2)/3
4013 reflections	(Δ/σ)max = 0.001
223 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 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	0.07338 (3)	0.25310 (17)	0.98816 (8)	0.0590 (3)
O2	0.10350 (4)	0.20839 (19)	1.15077 (8)	0.0675 (3)
O3	0.24539 (4)	−0.0059 (3)	1.28175 (9)	0.0877 (5)
O4	0.28280 (4)	−0.0482 (2)	1.17821 (10)	0.0851 (4)
O5	0.03857 (3)	0.18362 (17)	0.48812 (7)	0.0560 (3)
N1	0.11540 (4)	0.21520 (17)	0.85348 (8)	0.0444 (3)
H1N1	0.0924 (6)	0.258 (2)	0.8644 (13)	0.057 (5)*
N2	0.12306 (4)	0.22293 (16)	0.75869 (8)	0.0433 (3)
N3	0.10449 (4)	0.20867 (17)	1.06074 (8)	0.0455 (3)
N4	0.24971 (4)	−0.0049 (2)	1.19497 (10)	0.0585 (3)
C1	0.14719 (4)	0.16224 (18)	0.93741 (9)	0.0385 (3)
C2	0.14337 (4)	0.15613 (19)	1.03938 (9)	0.0390 (3)
C3	0.17682 (4)	0.10245 (19)	1.12370 (9)	0.0429 (3)
H3A	0.1738	0.1001	1.1900	0.052*
C4	0.21432 (4)	0.0530 (2)	1.10768 (10)	0.0446 (3)
C5	0.21945 (4)	0.0566 (2)	1.00856 (10)	0.0489 (3)
H5A	0.2451	0.0222	0.9991	0.059*
C6	0.18673 (4)	0.1105 (2)	0.92606 (10)	0.0469 (3)
H6A	0.1905	0.1134	0.8605	0.056*
C7	0.09330 (4)	0.28669 (19)	0.68182 (9)	0.0412 (3)
C8	0.10499 (4)	0.29961 (18)	0.58364 (9)	0.0399 (3)
C9	0.07723 (4)	0.24861 (19)	0.48709 (9)	0.0415 (3)
C10	0.09020 (5)	0.2587 (2)	0.39813 (10)	0.0482 (3)
H10A	0.0718	0.2241	0.3343	0.058*
C11	0.13047 (5)	0.3199 (2)	0.40454 (11)	0.0545 (4)
H11A	0.1390	0.3269	0.3449	0.065*
C12	0.15792 (5)	0.3706 (2)	0.49859 (12)	0.0546 (4)
H12A	0.1850	0.4119	0.5026	0.066*
C13	0.14525 (4)	0.3602 (2)	0.58725 (11)	0.0474 (3)
H13A	0.1641	0.3945	0.6506	0.057*
C14	0.05141 (5)	0.3552 (3)	0.68823 (11)	0.0571 (4)
H14A	0.0558	0.4461	0.7429	0.086*
H14B	0.0355	0.2515	0.7024	0.086*
H14C	0.0361	0.4121	0.6235	0.086*
C15	0.00827 (5)	0.1403 (3)	0.39214 (12)	0.0672 (5)
H15A	−0.0176	0.1009	0.4043	0.101*
H15B	0.0189	0.0410	0.3586	0.101*
H15C	0.0031	0.2495	0.3486	0.101*

	U11	U22	U33	U12	U13	U23
O1	0.0455 (5)	0.0817 (8)	0.0507 (6)	0.0075 (5)	0.0154 (5)	0.0039 (5)
O2	0.0637 (7)	0.1012 (9)	0.0455 (6)	0.0124 (6)	0.0285 (5)	0.0024 (6)
O3	0.0624 (7)	0.1543 (14)	0.0456 (6)	0.0142 (8)	0.0147 (5)	0.0277 (7)
O4	0.0485 (6)	0.1397 (13)	0.0658 (8)	0.0201 (7)	0.0149 (6)	0.0156 (8)
O5	0.0498 (6)	0.0784 (8)	0.0372 (5)	−0.0142 (5)	0.0087 (4)	−0.0049 (5)
N1	0.0461 (6)	0.0533 (7)	0.0342 (5)	0.0014 (5)	0.0127 (5)	−0.0016 (5)
N2	0.0496 (6)	0.0477 (6)	0.0325 (5)	−0.0008 (5)	0.0121 (4)	−0.0010 (4)
N3	0.0464 (6)	0.0521 (7)	0.0414 (6)	−0.0002 (5)	0.0183 (5)	−0.0005 (5)
N4	0.0457 (7)	0.0816 (10)	0.0463 (6)	0.0003 (6)	0.0106 (5)	0.0125 (6)
C1	0.0426 (6)	0.0387 (7)	0.0342 (6)	−0.0055 (5)	0.0112 (5)	−0.0019 (5)
C2	0.0415 (6)	0.0413 (7)	0.0365 (6)	−0.0044 (5)	0.0153 (5)	−0.0021 (5)
C3	0.0465 (7)	0.0486 (8)	0.0352 (6)	−0.0058 (6)	0.0143 (5)	0.0012 (5)
C4	0.0415 (7)	0.0525 (8)	0.0386 (6)	−0.0056 (6)	0.0098 (5)	0.0038 (5)
C5	0.0421 (7)	0.0627 (9)	0.0449 (7)	−0.0013 (6)	0.0172 (6)	0.0012 (6)
C6	0.0470 (7)	0.0595 (9)	0.0374 (6)	−0.0027 (6)	0.0173 (5)	−0.0012 (6)
C7	0.0452 (7)	0.0411 (7)	0.0361 (6)	−0.0033 (5)	0.0101 (5)	−0.0048 (5)
C8	0.0442 (7)	0.0388 (7)	0.0357 (6)	0.0040 (5)	0.0104 (5)	0.0025 (5)
C9	0.0458 (7)	0.0414 (7)	0.0356 (6)	0.0027 (6)	0.0094 (5)	0.0033 (5)
C10	0.0583 (8)	0.0498 (8)	0.0353 (6)	0.0055 (6)	0.0120 (6)	0.0043 (5)
C11	0.0655 (9)	0.0573 (9)	0.0475 (7)	0.0078 (7)	0.0272 (7)	0.0096 (6)
C12	0.0481 (8)	0.0565 (9)	0.0630 (9)	0.0004 (7)	0.0225 (7)	0.0094 (7)
C13	0.0448 (7)	0.0478 (8)	0.0465 (7)	−0.0003 (6)	0.0088 (6)	0.0031 (6)
C14	0.0512 (8)	0.0737 (11)	0.0454 (7)	0.0067 (7)	0.0128 (6)	−0.0095 (7)
C15	0.0522 (9)	0.0965 (14)	0.0443 (8)	−0.0065 (9)	0.0012 (7)	−0.0053 (8)

O1—N3	1.2347 (15)	C6—H6A	0.9300
O2—N3	1.2251 (14)	C7—C8	1.4889 (16)
O3—N4	1.2212 (16)	C7—C14	1.497 (2)
O4—N4	1.2215 (17)	C8—C13	1.3880 (19)
O5—C9	1.3649 (17)	C8—C9	1.4029 (17)
O5—C15	1.4186 (17)	C9—C10	1.3914 (17)
N1—C1	1.3526 (17)	C10—C11	1.381 (2)
N1—N2	1.3768 (14)	C10—H10A	0.9300
N1—H1N1	0.871 (18)	C11—C12	1.373 (2)
N2—C7	1.2845 (17)	C11—H11A	0.9300
N3—C2	1.4490 (16)	C12—C13	1.3819 (19)
N4—C4	1.4546 (18)	C12—H12A	0.9300
C1—C6	1.4110 (18)	C13—H13A	0.9300
C1—C2	1.4193 (15)	C14—H14A	0.9600
C2—C3	1.3869 (18)	C14—H14B	0.9600
C3—C4	1.3678 (18)	C14—H14C	0.9600
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.3976 (18)	C15—H15B	0.9600
C5—C6	1.3597 (19)	C15—H15C	0.9600
C5—H5A	0.9300
C9—O5—C15	118.48 (11)	C8—C7—C14	121.33 (12)
C1—N1—N2	118.56 (11)	C13—C8—C9	118.18 (12)
C1—N1—H1N1	117.2 (11)	C13—C8—C7	119.15 (11)
N2—N1—H1N1	123.6 (11)	C9—C8—C7	122.65 (12)
C7—N2—N1	117.18 (11)	O5—C9—C10	123.75 (12)
O2—N3—O1	121.81 (11)	O5—C9—C8	115.96 (11)
O2—N3—C2	118.84 (11)	C10—C9—C8	120.24 (12)
O1—N3—C2	119.35 (10)	C11—C10—C9	120.03 (13)
O3—N4—O4	122.78 (13)	C11—C10—H10A	120.0
O3—N4—C4	118.94 (13)	C9—C10—H10A	120.0
O4—N4—C4	118.27 (12)	C12—C11—C10	120.27 (13)
N1—C1—C6	119.96 (11)	C12—C11—H11A	119.9
N1—C1—C2	123.41 (11)	C10—C11—H11A	119.9
C6—C1—C2	116.63 (11)	C11—C12—C13	119.94 (13)
C3—C2—C1	121.74 (11)	C11—C12—H12A	120.0
C3—C2—N3	116.67 (10)	C13—C12—H12A	120.0
C1—C2—N3	121.58 (11)	C12—C13—C8	121.33 (13)
C4—C3—C2	118.91 (11)	C12—C13—H13A	119.3
C4—C3—H3A	120.5	C8—C13—H13A	119.3
C2—C3—H3A	120.5	C7—C14—H14A	109.5
C3—C4—C5	121.27 (12)	C7—C14—H14B	109.5
C3—C4—N4	119.79 (11)	H14A—C14—H14B	109.5
C5—C4—N4	118.94 (12)	C7—C14—H14C	109.5
C6—C5—C4	119.77 (12)	H14A—C14—H14C	109.5
C6—C5—H5A	120.1	H14B—C14—H14C	109.5
C4—C5—H5A	120.1	O5—C15—H15A	109.5
C5—C6—C1	121.68 (11)	O5—C15—H15B	109.5
C5—C6—H6A	119.2	H15A—C15—H15B	109.5
C1—C6—H6A	119.2	O5—C15—H15C	109.5
N2—C7—C8	113.69 (11)	H15A—C15—H15C	109.5
N2—C7—C14	124.87 (12)	H15B—C15—H15C	109.5
C1—N1—N2—C7	−175.05 (13)	N1—C1—C6—C5	179.97 (13)
N2—N1—C1—C6	−2.06 (19)	C2—C1—C6—C5	0.3 (2)
N2—N1—C1—C2	177.53 (12)	N1—N2—C7—C8	176.97 (11)
N1—C1—C2—C3	−179.48 (13)	N1—N2—C7—C14	0.9 (2)
C6—C1—C2—C3	0.13 (19)	N2—C7—C8—C13	−39.91 (17)
N1—C1—C2—N3	−0.5 (2)	C14—C7—C8—C13	136.32 (15)
C6—C1—C2—N3	179.12 (12)	N2—C7—C8—C9	138.53 (14)
O2—N3—C2—C3	2.10 (19)	C14—C7—C8—C9	−45.24 (19)
O1—N3—C2—C3	−178.19 (13)	C15—O5—C9—C10	−6.2 (2)
O2—N3—C2—C1	−176.94 (13)	C15—O5—C9—C8	176.37 (14)
O1—N3—C2—C1	2.8 (2)	C13—C8—C9—O5	177.73 (12)
C1—C2—C3—C4	−0.4 (2)	C7—C8—C9—O5	−0.73 (19)
N3—C2—C3—C4	−179.47 (12)	C13—C8—C9—C10	0.2 (2)
C2—C3—C4—C5	0.3 (2)	C7—C8—C9—C10	−178.24 (12)
C2—C3—C4—N4	−179.60 (13)	O5—C9—C10—C11	−177.64 (13)
O3—N4—C4—C3	−1.0 (2)	C8—C9—C10—C11	−0.3 (2)
O4—N4—C4—C3	179.99 (15)	C9—C10—C11—C12	0.2 (2)
O3—N4—C4—C5	179.15 (16)	C10—C11—C12—C13	0.1 (2)
O4—N4—C4—C5	0.1 (2)	C11—C12—C13—C8	−0.2 (2)
C3—C4—C5—C6	0.2 (2)	C9—C8—C13—C12	0.0 (2)
N4—C4—C5—C6	−179.93 (14)	C7—C8—C13—C12	178.55 (13)
C4—C5—C6—C1	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1	0.87 (2)	1.952 (18)	2.6086 (17)	131.1 (15)
C6—H6A···O3i	0.93	2.48	3.218 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1	0.87 (2)	1.952 (18)	2.6086 (17)	131.1 (15)
C6—H6A⋯O3i	0.93	2.48	3.218 (2)	136

Symmetry code: (i) .