4-[1-(Hydroxy-imino)ethyl]-N-(4-nitro-benzyl-idene)aniline.

In the title compound, C(15)H(13)N(3)O(3), the dihedral angle formed by the two benzene rings is 44.23 (2)°. The crystal structure is stabilized by aromatic π-π stacking inter-actions, with centroid-centroid distances of 3.825 (3) and 3.870 (4) Å between the aniline and the nitro-benzene rings of neighbouring mol-ecules, respectively. In addition, the stacked mol-ecules exhibit inter-molecular C-H⋯N and C-H⋯O inter-actions.

Related literature

For background to Schiff bases, see: Lozier et al. (1975 ▶). For the synthesis, see: Rafiq et al. (2008 ▶); Duan et al. (2007 ▶); Dong et al. (2008 ▶). For related structures, see: Bomfim et al. (2005 ▶); Fun et al. (2008 ▶).

Experimental

Crystal data

C15H13N3O3

M = 283.28

Orthorhombic,

a = 7.375 (1) Å

b = 10.770 (2) Å

c = 16.906 (2) Å

V = 1342.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.50 × 0.35 × 0.10 mm

Data collection

Bruker SMART1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.990

7656 measured reflections

1700 independent reflections

899 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.03

1700 reflections

195 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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 datablocks 2, I. DOI: 10.1107/S1600536809033753/lx2109sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033753/lx2109Isup2.hkl

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

C15H13N3O3	F(000) = 592
Mr = 283.28	Dx = 1.401 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1209 reflections
a = 7.375 (1) Å	θ = 2.2–21.4°
b = 10.770 (2) Å	µ = 0.10 mm−1
c = 16.906 (2) Å	T = 298 K
V = 1342.8 (3) Å3	Block-like, pale-yellow
Z = 4	0.50 × 0.35 × 0.10 mm

Bruker SMART1000 CCD area-detector diffractometer	1700 independent reflections
Radiation source: fine-focus sealed tube	899 reflections with I > 2σ(I)
graphite	Rint = 0.068
phi and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.952, Tmax = 0.990	k = −13→13
7656 measured reflections	l = −14→21

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.0834P] where P = (Fo2 + 2Fc2)/3
1700 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.20 e Å−3
2 restraints	Δρmin = −0.17 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
N1	0.7084 (5)	0.5375 (3)	0.90756 (16)	0.0478 (9)
N2	0.6140 (4)	0.6960 (3)	0.54920 (16)	0.0389 (8)
N3	0.6281 (5)	0.8627 (4)	0.1831 (2)	0.0601 (11)
O1	0.7150 (4)	0.5267 (3)	0.99032 (15)	0.0636 (10)
H1	0.784 (6)	0.454 (4)	0.999 (3)	0.100 (18)*
O2	0.6733 (5)	0.9635 (3)	0.15589 (17)	0.0830 (11)
O3	0.5894 (6)	0.7723 (3)	0.14311 (17)	0.0939 (13)
C1	0.5534 (7)	0.7318 (4)	0.9402 (2)	0.0755 (15)
H1A	0.5821	0.7090	0.9936	0.113*
H1B	0.4241	0.7352	0.9339	0.113*
H1C	0.6046	0.8117	0.9286	0.113*
C2	0.6304 (5)	0.6371 (3)	0.8846 (2)	0.0384 (9)
C3	0.6214 (5)	0.6542 (3)	0.79802 (19)	0.0319 (9)
C4	0.5531 (5)	0.7611 (3)	0.76460 (19)	0.0394 (10)
H4	0.5084	0.8235	0.7972	0.047*
C5	0.5498 (5)	0.7776 (3)	0.6832 (2)	0.0391 (10)
H5	0.5041	0.8510	0.6621	0.047*
C6	0.6133 (5)	0.6869 (3)	0.63323 (19)	0.0328 (9)
C7	0.6787 (5)	0.5777 (3)	0.6663 (2)	0.0381 (10)
H7	0.7201	0.5145	0.6334	0.046*
C8	0.6832 (5)	0.5618 (3)	0.7469 (2)	0.0377 (9)
H8	0.7283	0.4880	0.7677	0.045*
C9	0.6249 (5)	0.8019 (3)	0.5170 (2)	0.0402 (10)
H9	0.6364	0.8719	0.5489	0.048*
C10	0.6198 (5)	0.8171 (3)	0.43071 (19)	0.0375 (10)
C11	0.6747 (5)	0.9298 (3)	0.3977 (2)	0.0454 (11)
H11	0.7098	0.9948	0.4305	0.055*
C12	0.6773 (5)	0.9453 (4)	0.3167 (2)	0.0466 (11)
H12	0.7156	1.0198	0.2944	0.056*
C13	0.6223 (5)	0.8484 (4)	0.2699 (2)	0.0407 (10)
C14	0.5622 (5)	0.7378 (3)	0.3007 (2)	0.0436 (11)
H14	0.5223	0.6743	0.2678	0.052*
C15	0.5627 (5)	0.7232 (3)	0.3816 (2)	0.0405 (10)
H15	0.5237	0.6485	0.4034	0.049*

	U11	U22	U33	U12	U13	U23
N1	0.069 (3)	0.0466 (19)	0.0279 (16)	0.0068 (19)	−0.0017 (17)	0.0065 (15)
N2	0.043 (2)	0.0377 (17)	0.0363 (18)	0.0016 (17)	0.0005 (16)	0.0021 (14)
N3	0.060 (3)	0.080 (3)	0.040 (2)	0.017 (3)	0.003 (2)	0.013 (2)
O1	0.097 (3)	0.0590 (19)	0.0348 (15)	0.014 (2)	−0.0051 (16)	0.0064 (14)
O2	0.100 (3)	0.094 (2)	0.0551 (19)	0.010 (2)	0.0065 (19)	0.0338 (19)
O3	0.139 (4)	0.100 (3)	0.0422 (19)	0.005 (3)	−0.002 (2)	−0.0081 (19)
C1	0.111 (4)	0.072 (3)	0.044 (2)	0.031 (3)	−0.003 (3)	−0.011 (2)
C2	0.043 (3)	0.034 (2)	0.038 (2)	−0.007 (2)	0.0012 (18)	−0.0009 (17)
C3	0.030 (2)	0.034 (2)	0.032 (2)	−0.0030 (19)	−0.0013 (17)	0.0024 (16)
C4	0.042 (3)	0.038 (2)	0.038 (2)	0.002 (2)	0.0005 (18)	−0.0033 (18)
C5	0.042 (3)	0.033 (2)	0.043 (2)	0.0047 (19)	−0.0014 (18)	0.0071 (17)
C6	0.034 (2)	0.037 (2)	0.027 (2)	−0.0009 (19)	0.0004 (17)	0.0015 (15)
C7	0.042 (3)	0.035 (2)	0.037 (2)	−0.001 (2)	0.0061 (19)	−0.0006 (17)
C8	0.043 (3)	0.0325 (19)	0.037 (2)	0.002 (2)	−0.0015 (18)	0.0024 (17)
C9	0.044 (3)	0.041 (2)	0.035 (2)	0.000 (2)	−0.0051 (19)	−0.0031 (17)
C10	0.038 (3)	0.039 (2)	0.035 (2)	0.0029 (19)	0.0034 (19)	−0.0022 (17)
C11	0.045 (3)	0.042 (2)	0.049 (2)	0.002 (2)	−0.005 (2)	0.0022 (18)
C12	0.048 (3)	0.042 (2)	0.050 (3)	0.004 (2)	0.000 (2)	0.0166 (19)
C13	0.039 (3)	0.051 (2)	0.032 (2)	0.013 (2)	0.0026 (18)	0.0079 (18)
C14	0.043 (3)	0.044 (2)	0.044 (2)	0.008 (2)	−0.0051 (18)	−0.0009 (19)
C15	0.039 (3)	0.042 (2)	0.041 (2)	0.003 (2)	0.0038 (18)	0.0064 (18)

N1—C2	1.278 (4)	C5—H5	0.9300
N1—O1	1.405 (4)	C6—C7	1.388 (4)
N2—C9	1.266 (4)	C7—C8	1.375 (5)
N2—C6	1.424 (4)	C7—H7	0.9300
N3—O3	1.219 (4)	C8—H8	0.9300
N3—O2	1.225 (4)	C9—C10	1.469 (5)
N3—C13	1.476 (5)	C9—H9	0.9300
O1—H1	0.95 (4)	C10—C15	1.375 (5)
C1—C2	1.498 (5)	C10—C11	1.396 (5)
C1—H1A	0.9600	C11—C12	1.378 (5)
C1—H1B	0.9600	C11—H11	0.9300
C1—H1C	0.9600	C12—C13	1.371 (5)
C2—C3	1.477 (4)	C12—H12	0.9300
C3—C4	1.378 (4)	C13—C14	1.374 (5)
C3—C8	1.395 (4)	C14—C15	1.376 (4)
C4—C5	1.388 (4)	C14—H14	0.9300
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.374 (5)
C2—N1—O1	112.8 (3)	C8—C7—C6	120.9 (3)
C9—N2—C6	119.4 (3)	C8—C7—H7	119.6
O3—N3—O2	124.2 (4)	C6—C7—H7	119.6
O3—N3—C13	117.5 (4)	C7—C8—C3	121.1 (3)
O2—N3—C13	118.3 (4)	C7—C8—H8	119.4
N1—O1—H1	104 (3)	C3—C8—H8	119.4
C2—C1—H1A	109.5	N2—C9—C10	121.7 (3)
C2—C1—H1B	109.5	N2—C9—H9	119.1
H1A—C1—H1B	109.5	C10—C9—H9	119.1
C2—C1—H1C	109.5	C15—C10—C11	119.1 (3)
H1A—C1—H1C	109.5	C15—C10—C9	121.7 (3)
H1B—C1—H1C	109.5	C11—C10—C9	119.2 (3)
N1—C2—C3	115.2 (3)	C12—C11—C10	120.4 (4)
N1—C2—C1	123.5 (3)	C12—C11—H11	119.8
C3—C2—C1	121.3 (3)	C10—C11—H11	119.8
C4—C3—C8	117.5 (3)	C13—C12—C11	118.5 (4)
C4—C3—C2	121.8 (3)	C13—C12—H12	120.8
C8—C3—C2	120.7 (3)	C11—C12—H12	120.8
C3—C4—C5	121.3 (3)	C12—C13—C14	122.4 (3)
C3—C4—H4	119.3	C12—C13—N3	119.1 (4)
C5—C4—H4	119.3	C14—C13—N3	118.5 (4)
C6—C5—C4	120.8 (3)	C13—C14—C15	118.4 (4)
C6—C5—H5	119.6	C13—C14—H14	120.8
C4—C5—H5	119.6	C15—C14—H14	120.8
C5—C6—C7	118.3 (3)	C10—C15—C14	121.1 (4)
C5—C6—N2	124.4 (3)	C10—C15—H15	119.5
C7—C6—N2	117.3 (3)	C14—C15—H15	119.5
O1—N1—C2—C3	179.3 (3)	C6—N2—C9—C10	−177.8 (3)
O1—N1—C2—C1	−0.3 (6)	N2—C9—C10—C15	15.0 (6)
N1—C2—C3—C4	−175.2 (3)	N2—C9—C10—C11	−164.9 (4)
C1—C2—C3—C4	4.4 (6)	C15—C10—C11—C12	−2.1 (6)
N1—C2—C3—C8	4.4 (5)	C9—C10—C11—C12	177.8 (3)
C1—C2—C3—C8	−175.9 (4)	C10—C11—C12—C13	1.0 (6)
C8—C3—C4—C5	−1.5 (5)	C11—C12—C13—C14	1.0 (6)
C2—C3—C4—C5	178.2 (4)	C11—C12—C13—N3	−178.7 (4)
C3—C4—C5—C6	0.6 (6)	O3—N3—C13—C12	175.4 (4)
C4—C5—C6—C7	0.8 (6)	O2—N3—C13—C12	−3.7 (6)
C4—C5—C6—N2	179.7 (3)	O3—N3—C13—C14	−4.3 (6)
C9—N2—C6—C5	28.3 (6)	O2—N3—C13—C14	176.5 (4)
C9—N2—C6—C7	−152.8 (4)	C12—C13—C14—C15	−1.9 (6)
C5—C6—C7—C8	−1.3 (6)	N3—C13—C14—C15	177.8 (4)
N2—C6—C7—C8	179.8 (3)	C11—C10—C15—C14	1.3 (6)
C6—C7—C8—C3	0.4 (6)	C9—C10—C15—C14	−178.6 (3)
C4—C3—C8—C7	1.0 (6)	C13—C14—C15—C10	0.7 (6)
C2—C3—C8—C7	−178.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.95 (4)	1.97 (4)	2.887 (4)	162 (4)
C1—H1A···O3ii	0.96	2.62	3.469 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.95 (4)	1.97 (4)	2.887 (4)	162 (4)
C1—H1A⋯O3ii	0.96	2.62	3.469 (5)	148

Symmetry codes: (i) ; (ii) .