2-{(E)-[(2-Methyl-3-nitro-phen-yl)imino]-meth-yl}-4-nitro-phenol.

The title compound, C14H11N3O5, is a Schiff base that adopts the enol-imine tautomeric form in the solid state. The dihedral angle between the aromatic rings is 37.4 (3)° and the dihedral angles between the nitro groups and their attached rings are 4.0 (6) and 46.2 (8)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯N hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by C-H⋯O interactions, forming a two-dimensional network parallel to the bc plane.

Related literature

For the biological properties of Schiff bases, see: Aydoğan et al. (2001 ▶); Taggi et al. (2002 ▶); Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶); Cohen et al. (1964 ▶); Moustakali-Mavridis et al. (1978 ▶). For tautomeric forms of n class="Chemical">Schiff base compounds, see: Tanak et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Tanak (2011 ▶).

Experimental

Crystal data

C14H11N3O5

M = 301.26

Monoclinic,

a = 3.754 (5) Å

b = 15.696 (5) Å

c = 23.149 (5) Å

β = 93.491 (5)°

V = 1361.5 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.46 × 0.20 × 0.05 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.600, T max = 0.976

7609 measured reflections

2538 independent reflections

923 reflections with I > 2σ(I)

R int = 0.181

Refinement

R[F 2 > 2σ(F 2)] = 0.095

wR(F 2) = 0.229

S = 0.97

2538 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813015407/bt6911sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015407/bt6911Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015407/bt6911Isup3.cml

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

C14H11N3O5	F(000) = 624
Mr = 301.26	Dx = 1.470 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6502 reflections
a = 3.754 (5) Å	θ = 1.6–26.2°
b = 15.696 (5) Å	µ = 0.11 mm−1
c = 23.149 (5) Å	T = 296 K
β = 93.491 (5)°	Stick, yellow
V = 1361.5 (19) Å3	0.46 × 0.20 × 0.05 mm
Z = 4

Stoe IPDS II diffractometer	2538 independent reflections
Radiation source: fine-focus sealed tube	923 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.181
Detector resolution: 6.67 pixels mm-1	θmax = 25.7°, θmin = 1.6°
rotation method scans	h = −4→4
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −18→19
Tmin = 0.600, Tmax = 0.976	l = −22→28
7609 measured reflections

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)] = 0.095	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.229	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0591P)2] where P = (Fo2 + 2Fc2)/3
2538 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. 215 frames, detector distance = 130 mm

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
O3	0.7299 (11)	0.2631 (3)	0.1412 (2)	0.0806 (15)
H2	0.7392	0.2252	0.1656	0.121*
O2	0.0339 (12)	0.0664 (4)	−0.0715 (2)	0.0844 (15)
N2	0.6571 (12)	0.1125 (4)	0.1845 (2)	0.0592 (14)
N1	0.1412 (12)	0.1407 (4)	−0.0677 (2)	0.0635 (15)
C13	0.6662 (13)	0.0823 (4)	0.2872 (3)	0.0533 (16)
O1	0.1280 (16)	0.1866 (4)	−0.1100 (3)	0.110 (2)
C1	0.4754 (13)	0.1458 (4)	0.0866 (3)	0.0536 (16)
C7	0.5162 (13)	0.0880 (4)	0.1361 (3)	0.0579 (17)
H7	0.4371	0.0321	0.1321	0.070*
C10	0.8803 (16)	−0.0853 (5)	0.2670 (3)	0.0689 (19)
H10	0.9492	−0.1411	0.2600	0.083*
C11	0.8347 (15)	−0.0593 (5)	0.3228 (3)	0.0677 (18)
H11	0.8708	−0.0967	0.3537	0.081*
C5	0.2981 (13)	0.1707 (4)	−0.0126 (3)	0.0559 (16)
C6	0.3326 (13)	0.1173 (4)	0.0339 (3)	0.0564 (16)
H6	0.2586	0.0610	0.0299	0.068*
C12	0.7342 (14)	0.0238 (5)	0.3314 (3)	0.0610 (18)
O4	0.8401 (14)	0.1172 (4)	0.4082 (2)	0.1012 (18)
N3	0.7006 (16)	0.0501 (5)	0.3918 (3)	0.0765 (17)
C4	0.4026 (15)	0.2570 (5)	−0.0082 (3)	0.068 (2)
H4	0.3767	0.2933	−0.0400	0.082*
C2	0.5843 (14)	0.2325 (5)	0.0912 (3)	0.0608 (18)
C9	0.8248 (14)	−0.0294 (5)	0.2215 (3)	0.0643 (18)
H9	0.8636	−0.0472	0.1840	0.077*
C3	0.5415 (16)	0.2853 (5)	0.0436 (3)	0.0676 (19)
H3	0.6103	0.3421	0.0472	0.081*
O5	0.5514 (16)	0.0028 (5)	0.4243 (3)	0.114 (2)
C8	0.7111 (12)	0.0532 (4)	0.2312 (3)	0.0535 (16)
C14	0.5391 (16)	0.1734 (4)	0.2969 (3)	0.0726 (19)
H14A	0.5093	0.2023	0.2604	0.109*
H14B	0.7128	0.2029	0.3216	0.109*
H14C	0.3153	0.1720	0.3149	0.109*

	U11	U22	U33	U12	U13	U23
O3	0.091 (3)	0.065 (4)	0.083 (4)	−0.017 (2)	−0.011 (3)	−0.012 (3)
O2	0.107 (3)	0.066 (4)	0.079 (4)	−0.024 (3)	−0.002 (3)	−0.005 (3)
N2	0.056 (3)	0.057 (4)	0.064 (4)	−0.002 (2)	0.003 (3)	−0.007 (3)
N1	0.074 (3)	0.059 (5)	0.058 (4)	−0.002 (3)	0.005 (3)	0.003 (3)
C13	0.051 (3)	0.049 (4)	0.060 (4)	0.001 (3)	0.001 (3)	−0.007 (3)
O1	0.165 (5)	0.086 (5)	0.075 (4)	−0.011 (4)	−0.013 (3)	0.018 (3)
C1	0.049 (3)	0.049 (5)	0.062 (4)	−0.005 (3)	−0.001 (3)	−0.001 (3)
C7	0.051 (3)	0.053 (5)	0.069 (5)	0.000 (3)	0.002 (3)	−0.005 (4)
C10	0.078 (4)	0.051 (5)	0.076 (5)	0.007 (3)	−0.005 (4)	−0.002 (4)
C11	0.076 (4)	0.055 (5)	0.071 (5)	0.004 (3)	−0.005 (3)	0.003 (4)
C5	0.052 (3)	0.051 (5)	0.064 (5)	0.001 (3)	−0.002 (3)	−0.006 (4)
C6	0.056 (3)	0.047 (4)	0.066 (5)	−0.006 (3)	0.001 (3)	−0.001 (4)
C12	0.055 (3)	0.063 (5)	0.064 (5)	−0.002 (3)	−0.006 (3)	−0.007 (4)
O4	0.115 (4)	0.089 (5)	0.099 (4)	−0.007 (3)	−0.004 (3)	−0.027 (3)
N3	0.083 (4)	0.071 (5)	0.074 (5)	0.010 (3)	−0.005 (3)	−0.002 (4)
C4	0.061 (4)	0.054 (5)	0.090 (6)	0.003 (3)	0.002 (4)	0.003 (4)
C2	0.056 (3)	0.063 (5)	0.062 (5)	−0.003 (3)	−0.005 (3)	−0.008 (4)
C9	0.058 (3)	0.061 (5)	0.073 (5)	0.003 (3)	−0.003 (3)	−0.015 (4)
C3	0.076 (4)	0.054 (5)	0.072 (5)	−0.005 (3)	0.002 (4)	0.000 (4)
O5	0.140 (5)	0.112 (6)	0.093 (5)	−0.012 (4)	0.027 (4)	0.023 (4)
C8	0.040 (3)	0.060 (5)	0.059 (5)	−0.005 (3)	−0.006 (3)	−0.001 (4)
C14	0.077 (4)	0.060 (5)	0.081 (5)	0.015 (3)	0.001 (3)	−0.011 (4)

O3—C2	1.339 (7)	C11—C12	1.375 (9)
O3—H2	0.8200	C11—H11	0.9300
O2—N1	1.235 (7)	C5—C6	1.364 (9)
N2—C7	1.269 (7)	C5—C4	1.412 (9)
N2—C8	1.430 (8)	C6—H6	0.9300
N1—O1	1.214 (7)	C12—N3	1.469 (9)
N1—C5	1.451 (8)	O4—N3	1.228 (8)
C13—C12	1.388 (9)	N3—O5	1.217 (8)
C13—C8	1.395 (8)	C4—C3	1.353 (9)
C13—C14	1.528 (9)	C4—H4	0.9300
C1—C6	1.377 (8)	C2—C3	1.382 (9)
C1—C2	1.423 (9)	C9—C8	1.388 (9)
C1—C7	1.462 (9)	C9—H9	0.9300
C7—H7	0.9300	C3—H3	0.9300
C10—C11	1.374 (9)	C14—H14A	0.9600
C10—C9	1.377 (9)	C14—H14B	0.9600
C10—H10	0.9300	C14—H14C	0.9600
C2—O3—H2	109.5	C11—C12—N3	116.4 (6)
C7—N2—C8	120.2 (6)	C13—C12—N3	119.5 (7)
O1—N1—O2	120.5 (6)	O5—N3—O4	122.4 (8)
O1—N1—C5	120.7 (7)	O5—N3—C12	119.0 (7)
O2—N1—C5	118.8 (6)	O4—N3—C12	118.5 (7)
C12—C13—C8	116.2 (6)	C3—C4—C5	118.0 (7)
C12—C13—C14	123.7 (6)	C3—C4—H4	121.0
C8—C13—C14	120.0 (6)	C5—C4—H4	121.0
C6—C1—C2	118.1 (6)	O3—C2—C3	119.7 (7)
C6—C1—C7	120.7 (6)	O3—C2—C1	120.6 (6)
C2—C1—C7	121.2 (6)	C3—C2—C1	119.7 (6)
N2—C7—C1	121.6 (6)	C10—C9—C8	120.3 (7)
N2—C7—H7	119.2	C10—C9—H9	119.8
C1—C7—H7	119.2	C8—C9—H9	119.8
C11—C10—C9	120.5 (7)	C4—C3—C2	122.0 (7)
C11—C10—H10	119.7	C4—C3—H3	119.0
C9—C10—H10	119.7	C2—C3—H3	119.0
C10—C11—C12	118.0 (7)	C9—C8—C13	120.8 (6)
C10—C11—H11	121.0	C9—C8—N2	121.1 (6)
C12—C11—H11	121.0	C13—C8—N2	118.0 (6)
C6—C5—C4	121.3 (6)	C13—C14—H14A	109.5
C6—C5—N1	120.5 (6)	C13—C14—H14B	109.5
C4—C5—N1	118.1 (6)	H14A—C14—H14B	109.5
C5—C6—C1	120.9 (6)	C13—C14—H14C	109.5
C5—C6—H6	119.6	H14A—C14—H14C	109.5
C1—C6—H6	119.6	H14B—C14—H14C	109.5
C11—C12—C13	124.0 (7)
C8—N2—C7—C1	−176.5 (5)	C11—C12—N3—O4	132.5 (6)
C6—C1—C7—N2	177.9 (5)	C13—C12—N3—O4	−47.3 (8)
C2—C1—C7—N2	−1.6 (8)	C6—C5—C4—C3	0.5 (8)
C9—C10—C11—C12	−0.3 (9)	N1—C5—C4—C3	178.6 (5)
O1—N1—C5—C6	−176.0 (6)	C6—C1—C2—O3	−179.0 (5)
O2—N1—C5—C6	1.3 (8)	C7—C1—C2—O3	0.5 (8)
O1—N1—C5—C4	6.0 (8)	C6—C1—C2—C3	0.6 (8)
O2—N1—C5—C4	−176.8 (5)	C7—C1—C2—C3	−179.9 (5)
C4—C5—C6—C1	−0.9 (9)	C11—C10—C9—C8	−2.0 (9)
N1—C5—C6—C1	−178.9 (5)	C5—C4—C3—C2	0.4 (9)
C2—C1—C6—C5	0.3 (8)	O3—C2—C3—C4	178.6 (6)
C7—C1—C6—C5	−179.2 (5)	C1—C2—C3—C4	−0.9 (9)
C10—C11—C12—C13	1.9 (9)	C10—C9—C8—C13	2.8 (8)
C10—C11—C12—N3	−177.9 (5)	C10—C9—C8—N2	179.1 (5)
C8—C13—C12—C11	−1.1 (8)	C12—C13—C8—C9	−1.3 (7)
C14—C13—C12—C11	177.3 (6)	C14—C13—C8—C9	−179.7 (5)
C8—C13—C12—N3	178.7 (5)	C12—C13—C8—N2	−177.6 (5)
C14—C13—C12—N3	−3.0 (8)	C14—C13—C8—N2	3.9 (7)
C11—C12—N3—O5	−44.0 (8)	C7—N2—C8—C9	39.8 (7)
C13—C12—N3—O5	136.2 (6)	C7—N2—C8—C13	−143.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H2···N2	0.82	1.85	2.589 (8)	149
C6—H6···O2i	0.93	2.50	3.333 (9)	149
C4—H4···O4ii	0.93	2.59	3.274 (9)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H2⋯N2	0.82	1.85	2.589 (8)	149
C6—H6⋯O2i	0.93	2.50	3.333 (9)	149
C4—H4⋯O4ii	0.93	2.59	3.274 (9)	131

Symmetry codes: (i) ; (ii) .