5-Hy-droxy-2-{(E)-[(3-nitro-phen-yl)iminio]meth-yl}phenolate.

The title compound, C(13)H(10)N(2)O(4), crystallized as the zwitterionic tautomer. As a result, the phenolate C-O(-) bond [1.296 (2) Å] is shorter than a normal Csp(2)-O(H) bond, and the azomethine C=N bond [1.314 (2) Å] is longer than a normal C=N double bond. The mol-ecule is nearly planar, the mean plane of the nitro-substituted benzene ring forming dihedral angles of 9.83 (7) and 8.45 (9)° with the other benzene ring and with the nitro group, respectively. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. In the crystal, strong O-H⋯O hydrogen bonds link the mol-ecules into double-stranded chains along the b-axis direction. Within the chains there are π-π interactions involving the benzene rings of adjacent molecules [centroid-centroid distance = 3.669 (1) Å]. The chains are linked via C-H⋯O hydrogen bonds, forming R(2) (1)(6), R(2) (1)(7) and R(2) (2)(10) ring motifs.

Related literature

For related structures, see: Yeap et al. (1992 ▶); Hijji et al. (2009 ▶). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10N2O4

M = 258.23

Monoclinic,

a = 12.8518 (9) Å

b = 7.8501 (5) Å

c = 24.1316 (18) Å

β = 101.593 (3)°

V = 2384.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.30 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.975, T max = 0.985

5601 measured reflections

2126 independent reflections

1569 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.02

2126 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033740/yk2068sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033740/yk2068Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033740/yk2068Isup3.cml

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

C13H10N2O4	F(000) = 1072
Mr = 258.23	Dx = 1.438 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1569 reflections
a = 12.8518 (9) Å	θ = 3.1–25.3°
b = 7.8501 (5) Å	µ = 0.11 mm−1
c = 24.1316 (18) Å	T = 296 K
β = 101.593 (3)°	Prism, orange
V = 2384.9 (3) Å3	0.30 × 0.25 × 0.22 mm
Z = 8

Bruker Kappa APEXII CCD area-detector diffractometer	2126 independent reflections
Radiation source: fine-focus sealed tube	1569 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −9→8
Tmin = 0.975, Tmax = 0.985	l = −28→27
5601 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.8634P] where P = (Fo2 + 2Fc2)/3
2126 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.15 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 e.s.d.'s 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	0.15456 (11)	−0.19142 (18)	0.02818 (6)	0.0662 (5)
O2	0.20746 (12)	0.03661 (18)	−0.00681 (6)	0.0724 (6)
O3	0.62612 (10)	0.43187 (15)	0.22353 (5)	0.0534 (4)
O4	0.76284 (11)	0.95669 (16)	0.17361 (5)	0.0575 (5)
N1	0.21457 (12)	−0.0694 (2)	0.03061 (7)	0.0496 (6)
N2	0.49661 (11)	0.26941 (19)	0.14644 (6)	0.0474 (5)
C1	0.43511 (13)	0.1203 (2)	0.13474 (7)	0.0410 (6)
C2	0.35653 (14)	0.1006 (2)	0.08681 (7)	0.0421 (6)
C3	0.29944 (13)	−0.0494 (2)	0.08125 (7)	0.0414 (6)
C4	0.31558 (15)	−0.1781 (2)	0.12040 (8)	0.0481 (6)
C5	0.39528 (16)	−0.1569 (3)	0.16724 (8)	0.0530 (7)
C6	0.45478 (14)	−0.0106 (3)	0.17409 (7)	0.0487 (6)
C7	0.50024 (13)	0.4025 (2)	0.11385 (7)	0.0447 (6)
C8	0.56478 (13)	0.5432 (2)	0.13102 (7)	0.0405 (6)
C9	0.62972 (13)	0.5521 (2)	0.18714 (7)	0.0403 (6)
C10	0.69554 (13)	0.6942 (2)	0.20049 (7)	0.0406 (6)
C11	0.69865 (13)	0.8209 (2)	0.16195 (7)	0.0416 (6)
C12	0.63360 (14)	0.8146 (2)	0.10705 (7)	0.0461 (6)
C13	0.56882 (14)	0.6792 (2)	0.09292 (7)	0.0459 (6)
H2	0.34268	0.18528	0.05936	0.0505*
H2A	0.53731	0.27396	0.17938	0.0569*
H4	0.27414	−0.27611	0.11547	0.0578*
H4A	0.79725	0.94912	0.20604	0.0862*
H5	0.40893	−0.24223	0.19446	0.0636*
H6	0.50928	0.00111	0.20566	0.0584*
H7	0.45787	0.40280	0.07774	0.0536*
H10	0.73819	0.70276	0.23640	0.0487*
H12	0.63551	0.90201	0.08126	0.0553*
H13	0.52555	0.67518	0.05708	0.0551*

	U11	U22	U33	U12	U13	U23
O1	0.0630 (9)	0.0603 (9)	0.0709 (10)	−0.0201 (8)	0.0033 (7)	−0.0121 (7)
O2	0.0882 (12)	0.0606 (9)	0.0540 (9)	−0.0102 (8)	−0.0198 (8)	0.0103 (8)
O3	0.0592 (8)	0.0484 (7)	0.0437 (8)	−0.0070 (6)	−0.0110 (6)	0.0081 (6)
O4	0.0692 (9)	0.0485 (8)	0.0460 (8)	−0.0139 (7)	−0.0092 (6)	0.0048 (6)
N1	0.0527 (10)	0.0446 (9)	0.0478 (10)	−0.0009 (8)	0.0010 (7)	−0.0077 (8)
N2	0.0451 (9)	0.0506 (9)	0.0399 (9)	−0.0003 (8)	−0.0072 (6)	−0.0014 (7)
C1	0.0396 (10)	0.0429 (10)	0.0386 (10)	0.0018 (8)	0.0037 (7)	−0.0030 (8)
C2	0.0469 (10)	0.0370 (10)	0.0389 (10)	0.0026 (8)	0.0002 (8)	0.0031 (7)
C3	0.0418 (10)	0.0400 (10)	0.0401 (10)	0.0022 (8)	0.0031 (8)	−0.0036 (8)
C4	0.0514 (11)	0.0426 (10)	0.0510 (11)	0.0008 (9)	0.0117 (9)	0.0057 (9)
C5	0.0567 (12)	0.0538 (12)	0.0484 (12)	0.0081 (10)	0.0103 (9)	0.0167 (9)
C6	0.0469 (11)	0.0619 (12)	0.0347 (10)	0.0056 (10)	0.0023 (8)	0.0053 (9)
C7	0.0391 (10)	0.0532 (11)	0.0374 (10)	0.0041 (9)	−0.0025 (8)	−0.0024 (9)
C8	0.0368 (9)	0.0432 (10)	0.0378 (10)	0.0029 (8)	−0.0016 (7)	−0.0044 (8)
C9	0.0391 (10)	0.0399 (10)	0.0385 (10)	0.0062 (8)	−0.0002 (7)	0.0001 (8)
C10	0.0414 (10)	0.0429 (10)	0.0318 (9)	0.0022 (8)	−0.0059 (7)	−0.0033 (8)
C11	0.0429 (10)	0.0391 (10)	0.0403 (10)	0.0018 (8)	0.0024 (8)	−0.0024 (8)
C12	0.0514 (11)	0.0479 (11)	0.0356 (10)	0.0027 (9)	0.0007 (8)	0.0050 (8)
C13	0.0462 (11)	0.0528 (11)	0.0337 (10)	0.0048 (9)	−0.0040 (8)	0.0004 (8)

O1—N1	1.224 (2)	C7—C8	1.393 (2)
O2—N1	1.218 (2)	C8—C13	1.417 (2)
O3—C9	1.296 (2)	C8—C9	1.443 (2)
O4—C11	1.343 (2)	C9—C10	1.398 (2)
O4—H4A	0.8200	C10—C11	1.368 (2)
N1—C3	1.474 (2)	C11—C12	1.418 (2)
N2—C7	1.314 (2)	C12—C13	1.351 (2)
N2—C1	1.409 (2)	C2—H2	0.9300
N2—H2A	0.8600	C4—H4	0.9300
C1—C6	1.388 (3)	C5—H5	0.9300
C1—C2	1.383 (2)	C6—H6	0.9300
C2—C3	1.380 (2)	C7—H7	0.9300
C3—C4	1.370 (2)	C10—H10	0.9300
C4—C5	1.375 (3)	C12—H12	0.9300
C5—C6	1.371 (3)	C13—H13	0.9300
C11—O4—H4A	109.00	C8—C9—C10	117.65 (14)
O1—N1—O2	123.14 (17)	C9—C10—C11	121.51 (15)
O1—N1—C3	118.52 (15)	O4—C11—C12	116.45 (14)
O2—N1—C3	118.35 (15)	O4—C11—C10	122.38 (15)
C1—N2—C7	128.80 (15)	C10—C11—C12	121.17 (15)
C7—N2—H2A	116.00	C11—C12—C13	118.74 (15)
C1—N2—H2A	116.00	C8—C13—C12	122.02 (16)
N2—C1—C2	123.13 (15)	C1—C2—H2	121.00
N2—C1—C6	117.42 (15)	C3—C2—H2	121.00
C2—C1—C6	119.45 (16)	C3—C4—H4	121.00
C1—C2—C3	117.49 (15)	C5—C4—H4	121.00
N1—C3—C2	117.52 (14)	C4—C5—H5	120.00
N1—C3—C4	118.52 (15)	C6—C5—H5	120.00
C2—C3—C4	123.95 (16)	C1—C6—H6	119.00
C3—C4—C5	117.53 (17)	C5—C6—H6	119.00
C4—C5—C6	120.39 (19)	N2—C7—H7	119.00
C1—C6—C5	121.15 (16)	C8—C7—H7	119.00
N2—C7—C8	122.88 (15)	C9—C10—H10	119.00
C7—C8—C13	120.11 (15)	C11—C10—H10	119.00
C7—C8—C9	121.00 (15)	C11—C12—H12	121.00
C9—C8—C13	118.88 (15)	C13—C12—H12	121.00
O3—C9—C8	120.53 (14)	C8—C13—H13	119.00
O3—C9—C10	121.82 (15)	C12—C13—H13	119.00
O1—N1—C3—C2	−171.10 (16)	C4—C5—C6—C1	1.1 (3)
O1—N1—C3—C4	7.6 (2)	N2—C7—C8—C9	−1.9 (3)
O2—N1—C3—C2	8.8 (2)	N2—C7—C8—C13	177.02 (16)
O2—N1—C3—C4	−172.56 (17)	C7—C8—C9—O3	−2.7 (3)
C7—N2—C1—C2	−8.0 (3)	C7—C8—C9—C10	177.49 (16)
C7—N2—C1—C6	172.80 (17)	C13—C8—C9—O3	178.36 (16)
C1—N2—C7—C8	179.59 (16)	C13—C8—C9—C10	−1.5 (2)
N2—C1—C2—C3	−177.80 (16)	C7—C8—C13—C12	−177.19 (17)
C6—C1—C2—C3	1.4 (3)	C9—C8—C13—C12	1.8 (3)
N2—C1—C6—C5	177.00 (17)	O3—C9—C10—C11	−179.76 (16)
C2—C1—C6—C5	−2.2 (3)	C8—C9—C10—C11	0.1 (2)
C1—C2—C3—N1	179.08 (15)	C9—C10—C11—O4	−178.67 (16)
C1—C2—C3—C4	0.5 (3)	C9—C10—C11—C12	1.1 (3)
N1—C3—C4—C5	179.88 (17)	O4—C11—C12—C13	178.96 (16)
C2—C3—C4—C5	−1.6 (3)	C10—C11—C12—C13	−0.9 (3)
C3—C4—C5—C6	0.7 (3)	C11—C12—C13—C8	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	1.87	2.5716 (19)	138
O4—H4A···O3i	0.82	1.79	2.6100 (17)	179
C2—H2···O2ii	0.93	2.54	3.446 (2)	164
C4—H4···O4iii	0.93	2.54	3.268 (2)	135
C7—H7···O2ii	0.93	2.49	3.355 (2)	154
C10—H10···O3i	0.93	2.56	3.226 (2)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.86	1.87	2.5716 (19)	138
O4—H4A⋯O3i	0.82	1.79	2.6100 (17)	179
C2—H2⋯O2ii	0.93	2.54	3.446 (2)	164
C4—H4⋯O4iii	0.93	2.54	3.268 (2)	135
C7—H7⋯O2ii	0.93	2.49	3.355 (2)	154
C10—H10⋯O3i	0.93	2.56	3.226 (2)	129

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