(E)-1-(2,4-Di-nitro-phen-yl)-2-(3-eth-oxy-4-hy-droxy-benzyl-idene)hydrazine.

The mol-ecule of the title hydrazine derivative, C15H14N4O6, is essentially planar, the dihedral angle between the substituted benzene rings being 2.25 (9)°. The eth-oxy and hy-droxy groups are almost coplanar with their bound benzene ring [r.m.s. deviation = 0.0153 (2) Å for the ten non-H atoms]. Intra-molecular N-H⋯O and O-H⋯Oeth-oxy hydrogen bonds generate S(6) and S(5) ring motifs, respectively. In the crystal, mol-ecules are linked by O-H⋯Onitro hydrogen bonds into chains propagating in [010]. Weak aromatic π-π inter-actions, with centroid-centroid distances of 3.8192 (19) and 4.0491 (19) Å, are also observed.

Related literature

For a related structure and background to hydrazones, see: Fun et al. (2013 ▶). For other related structures, see: Fun et al. (2011 ▶, 2012 ▶). For the measurement of anti-oxidant activity, see: Molyneux (2004 ▶).

Experimental

Crystal data

C15H14N4O6

M = 346.30

Monoclinic,

a = 10.245 (4) Å

b = 13.679 (5) Å

c = 14.184 (5) Å

β = 129.15 (2)°

V = 1541.5 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.52 × 0.37 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.941, T max = 0.992

16113 measured reflections

4060 independent reflections

2183 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.131

S = 1.01

4060 reflections

235 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.22 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, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033989/hb7175sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033989/hb7175Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033989/hb7175Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H14N4O6	F(000) = 720
Mr = 346.30	Dx = 1.492 Mg m−3
Monoclinic, P21/c	Melting point = 515–516 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.245 (4) Å	Cell parameters from 4060 reflections
b = 13.679 (5) Å	θ = 2.4–29.0°
c = 14.184 (5) Å	µ = 0.12 mm−1
β = 129.15 (2)°	T = 298 K
V = 1541.5 (11) Å3	Plate, orange
Z = 4	0.52 × 0.37 × 0.07 mm

Bruker APEXII CCD diffractometer	4060 independent reflections
Radiation source: sealed tube	2183 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 29.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.941, Tmax = 0.992	k = −18→18
16113 measured reflections	l = −13→19

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) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.0702P] where P = (Fo2 + 2Fc2)/3
4060 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.22 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	1.20079 (13)	−0.22891 (8)	0.16025 (12)	0.0622 (4)
O2	1.05019 (14)	−0.35272 (9)	0.13142 (13)	0.0736 (5)
O3	0.46877 (15)	−0.32518 (12)	−0.07366 (14)	0.0814 (5)
O4	0.36011 (15)	−0.18505 (11)	−0.08629 (13)	0.0767 (4)
O5	1.01832 (12)	0.42468 (8)	0.13492 (11)	0.0532 (3)
O6	1.32309 (16)	0.49799 (9)	0.24070 (13)	0.0580 (4)
H1O6	1.230 (3)	0.5246 (19)	0.209 (2)	0.121 (10)*
N1	1.09605 (18)	−0.05017 (10)	0.15152 (14)	0.0489 (4)
H1N1	1.183 (2)	−0.0854 (13)	0.1800 (17)	0.065 (6)*
N2	1.10133 (17)	0.05030 (9)	0.15757 (13)	0.0472 (4)
N3	1.06865 (16)	−0.26439 (10)	0.13050 (13)	0.0494 (4)
N4	0.47883 (17)	−0.23628 (13)	−0.05806 (14)	0.0594 (4)
C1	0.94828 (19)	−0.09698 (11)	0.10069 (14)	0.0411 (4)
C2	0.93039 (18)	−0.19991 (11)	0.09135 (14)	0.0409 (4)
C3	0.77777 (19)	−0.24509 (12)	0.04025 (14)	0.0452 (4)
H3A	0.7692	−0.3129	0.0357	0.054*
C4	0.63954 (19)	−0.18842 (12)	−0.00355 (15)	0.0463 (4)
C5	0.6511 (2)	−0.08732 (13)	0.00279 (16)	0.0523 (5)
H5A	0.5558	−0.0499	−0.0284	0.063*
C6	0.8015 (2)	−0.04225 (12)	0.05462 (16)	0.0509 (4)
H6A	0.8077	0.0256	0.0598	0.061*
C7	1.2451 (2)	0.08997 (12)	0.20969 (15)	0.0474 (4)
H7A	1.3388	0.0507	0.2419	0.057*
C8	1.26408 (19)	0.19596 (11)	0.21919 (14)	0.0432 (4)
C9	1.12420 (19)	0.25734 (11)	0.17161 (15)	0.0437 (4)
H9A	1.0192	0.2301	0.1360	0.052*
C10	1.14273 (18)	0.35742 (11)	0.17773 (15)	0.0432 (4)
C11	1.30253 (19)	0.39867 (12)	0.23335 (15)	0.0448 (4)
C12	1.43888 (19)	0.33878 (12)	0.28036 (16)	0.0510 (5)
H12A	1.5442	0.3661	0.3172	0.061*
C13	1.42040 (19)	0.23804 (12)	0.27326 (15)	0.0485 (4)
H13A	1.5134	0.1982	0.3049	0.058*
C14	0.84992 (18)	0.38972 (12)	0.07237 (16)	0.0509 (4)
H14A	0.8445	0.3497	0.1263	0.061*
H14B	0.8145	0.3504	0.0029	0.061*
C15	0.7378 (2)	0.47736 (13)	0.03131 (17)	0.0573 (5)
H15A	0.6249	0.4563	−0.0071	0.086*
H15B	0.7392	0.5143	−0.0256	0.086*
H15C	0.7775	0.5175	0.1003	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0395 (7)	0.0560 (8)	0.0861 (10)	0.0018 (5)	0.0373 (7)	−0.0034 (7)
O2	0.0515 (8)	0.0417 (8)	0.1069 (12)	0.0051 (6)	0.0401 (8)	0.0016 (7)
O3	0.0537 (8)	0.0706 (10)	0.1065 (12)	−0.0078 (7)	0.0442 (9)	0.0088 (9)
O4	0.0417 (7)	0.0993 (11)	0.0876 (11)	0.0102 (7)	0.0400 (8)	0.0084 (8)
O5	0.0389 (6)	0.0431 (6)	0.0697 (8)	−0.0035 (5)	0.0305 (6)	−0.0059 (6)
O6	0.0490 (7)	0.0453 (7)	0.0754 (9)	−0.0079 (6)	0.0373 (7)	−0.0069 (6)
N1	0.0437 (8)	0.0400 (8)	0.0605 (10)	0.0040 (6)	0.0317 (8)	0.0026 (7)
N2	0.0511 (8)	0.0400 (8)	0.0540 (9)	0.0007 (6)	0.0349 (8)	0.0014 (6)
N3	0.0402 (8)	0.0443 (9)	0.0555 (9)	0.0026 (6)	0.0264 (7)	−0.0023 (7)
N4	0.0415 (8)	0.0740 (11)	0.0609 (10)	0.0004 (8)	0.0314 (8)	0.0091 (9)
C1	0.0416 (9)	0.0437 (9)	0.0409 (9)	0.0031 (7)	0.0273 (8)	0.0016 (7)
C2	0.0359 (8)	0.0435 (9)	0.0430 (9)	0.0053 (7)	0.0248 (8)	0.0021 (7)
C3	0.0439 (9)	0.0476 (9)	0.0433 (10)	0.0018 (7)	0.0272 (8)	0.0024 (8)
C4	0.0373 (8)	0.0572 (11)	0.0457 (10)	0.0029 (7)	0.0269 (8)	0.0042 (8)
C5	0.0443 (10)	0.0602 (12)	0.0538 (11)	0.0141 (8)	0.0316 (9)	0.0064 (9)
C6	0.0512 (10)	0.0449 (10)	0.0597 (12)	0.0094 (8)	0.0364 (10)	0.0022 (8)
C7	0.0459 (9)	0.0479 (10)	0.0477 (10)	0.0039 (7)	0.0292 (9)	0.0029 (8)
C8	0.0438 (9)	0.0453 (10)	0.0411 (9)	−0.0005 (7)	0.0271 (8)	0.0018 (7)
C9	0.0369 (8)	0.0462 (10)	0.0449 (10)	−0.0053 (7)	0.0243 (8)	−0.0035 (8)
C10	0.0388 (8)	0.0470 (10)	0.0432 (10)	0.0001 (7)	0.0257 (8)	−0.0017 (8)
C11	0.0434 (9)	0.0459 (10)	0.0454 (10)	−0.0060 (7)	0.0282 (8)	−0.0048 (8)
C12	0.0386 (9)	0.0563 (11)	0.0564 (12)	−0.0071 (8)	0.0292 (9)	−0.0023 (9)
C13	0.0378 (9)	0.0538 (10)	0.0511 (11)	0.0038 (7)	0.0268 (8)	0.0042 (8)
C14	0.0371 (9)	0.0534 (10)	0.0586 (11)	−0.0046 (7)	0.0285 (9)	−0.0071 (9)
C15	0.0494 (10)	0.0560 (11)	0.0656 (13)	0.0055 (8)	0.0359 (10)	0.0026 (9)

O1—N3	1.2349 (16)	C5—C6	1.366 (2)
O2—N3	1.2243 (17)	C5—H5A	0.9300
O3—N4	1.229 (2)	C6—H6A	0.9300
O4—N4	1.2312 (18)	C7—C8	1.458 (2)
O5—C10	1.3647 (18)	C7—H7A	0.9300
O5—C14	1.4351 (18)	C8—C13	1.390 (2)
O6—C11	1.369 (2)	C8—C9	1.412 (2)
O6—H1O6	0.84 (3)	C9—C10	1.377 (2)
N1—C1	1.358 (2)	C9—H9A	0.9300
N1—N2	1.3759 (18)	C10—C11	1.411 (2)
N1—H1N1	0.858 (17)	C11—C12	1.375 (2)
N2—C7	1.279 (2)	C12—C13	1.386 (2)
N3—C2	1.4490 (19)	C12—H12A	0.9300
N4—C4	1.459 (2)	C13—H13A	0.9300
C1—C2	1.415 (2)	C14—C15	1.500 (2)
C1—C6	1.417 (2)	C14—H14A	0.9700
C2—C3	1.386 (2)	C14—H14B	0.9700
C3—C4	1.372 (2)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.386 (2)	C15—H15C	0.9600
C10—O5—C14	118.10 (12)	C8—C7—H7A	119.6
C11—O6—H1O6	108.7 (18)	C13—C8—C9	119.05 (15)
C1—N1—N2	119.40 (13)	C13—C8—C7	120.17 (15)
C1—N1—H1N1	117.7 (12)	C9—C8—C7	120.77 (14)
N2—N1—H1N1	122.9 (12)	C10—C9—C8	120.21 (14)
C7—N2—N1	116.45 (14)	C10—C9—H9A	119.9
O2—N3—O1	121.84 (13)	C8—C9—H9A	119.9
O2—N3—C2	118.99 (13)	O5—C10—C9	126.10 (14)
O1—N3—C2	119.17 (14)	O5—C10—C11	114.04 (14)
O3—N4—O4	123.46 (15)	C9—C10—C11	119.86 (14)
O3—N4—C4	118.54 (14)	O6—C11—C12	119.61 (14)
O4—N4—C4	118.00 (17)	O6—C11—C10	120.53 (14)
N1—C1—C2	123.64 (14)	C12—C11—C10	119.86 (15)
N1—C1—C6	119.91 (15)	C11—C12—C13	120.44 (15)
C2—C1—C6	116.45 (14)	C11—C12—H12A	119.8
C3—C2—C1	121.96 (14)	C13—C12—H12A	119.8
C3—C2—N3	115.85 (14)	C12—C13—C8	120.57 (15)
C1—C2—N3	122.15 (13)	C12—C13—H13A	119.7
C4—C3—C2	119.08 (16)	C8—C13—H13A	119.7
C4—C3—H3A	120.5	O5—C14—C15	107.50 (14)
C2—C3—H3A	120.5	O5—C14—H14A	110.2
C3—C4—C5	120.88 (15)	C15—C14—H14A	110.2
C3—C4—N4	118.90 (16)	O5—C14—H14B	110.2
C5—C4—N4	120.22 (14)	C15—C14—H14B	110.2
C6—C5—C4	120.41 (15)	H14A—C14—H14B	108.5
C6—C5—H5A	119.8	C14—C15—H15A	109.5
C4—C5—H5A	119.8	C14—C15—H15B	109.5
C5—C6—C1	121.21 (16)	H15A—C15—H15B	109.5
C5—C6—H6A	119.4	C14—C15—H15C	109.5
C1—C6—H6A	119.4	H15A—C15—H15C	109.5
N2—C7—C8	120.86 (15)	H15B—C15—H15C	109.5
N2—C7—H7A	119.6
C1—N1—N2—C7	177.98 (15)	N1—C1—C6—C5	179.86 (16)
N2—N1—C1—C2	−179.34 (15)	C2—C1—C6—C5	−0.8 (2)
N2—N1—C1—C6	0.0 (2)	N1—N2—C7—C8	178.99 (14)
N1—C1—C2—C3	179.14 (16)	N2—C7—C8—C13	−178.30 (15)
C6—C1—C2—C3	−0.2 (2)	N2—C7—C8—C9	0.3 (2)
N1—C1—C2—N3	−3.1 (3)	C13—C8—C9—C10	0.7 (2)
C6—C1—C2—N3	177.54 (15)	C7—C8—C9—C10	−177.94 (16)
O2—N3—C2—C3	−9.4 (2)	C14—O5—C10—C9	−3.1 (2)
O1—N3—C2—C3	169.55 (15)	C14—O5—C10—C11	177.49 (14)
O2—N3—C2—C1	172.77 (16)	C8—C9—C10—O5	179.66 (15)
O1—N3—C2—C1	−8.3 (2)	C8—C9—C10—C11	−0.9 (2)
C1—C2—C3—C4	0.6 (2)	O5—C10—C11—O6	−0.2 (2)
N3—C2—C3—C4	−177.29 (15)	C9—C10—C11—O6	−179.65 (15)
C2—C3—C4—C5	0.0 (2)	O5—C10—C11—C12	179.98 (15)
C2—C3—C4—N4	179.57 (15)	C9—C10—C11—C12	0.5 (3)
O3—N4—C4—C3	−7.0 (2)	O6—C11—C12—C13	−179.69 (16)
O4—N4—C4—C3	173.20 (15)	C10—C11—C12—C13	0.1 (3)
O3—N4—C4—C5	172.60 (17)	C11—C12—C13—C8	−0.4 (3)
O4—N4—C4—C5	−7.2 (2)	C9—C8—C13—C12	−0.1 (2)
C3—C4—C5—C6	−1.0 (3)	C7—C8—C13—C12	178.60 (16)
N4—C4—C5—C6	179.47 (16)	C10—O5—C14—C15	−178.05 (14)
C4—C5—C6—C1	1.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H1O6···O2i	0.84 (3)	2.21 (3)	2.986 (2)	155 (3)
O6—H1O6···O5	0.84 (3)	2.19 (3)	2.663 (3)	116 (2)
N1—H1N1···O1	0.86 (2)	2.007 (18)	2.641 (2)	130.0 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H1O6⋯O2i	0.84 (3)	2.21 (3)	2.986 (2)	155 (3)
O6—H1O6⋯O5	0.84 (3)	2.19 (3)	2.663 (3)	116 (2)
N1—H1N1⋯O1	0.86 (2)	2.007 (18)	2.641 (2)	130.0 (18)

Symmetry code: (i) .