(E)-4-Hy-droxy-2-[(2-hy-droxy-phen-yl)iminiometh-yl]phenolate.

The title compound, C(13)H(11)NO(3), crystallizes in a zwitterionic form and has a trans configuration about the C=N bond. The mol-ecule is almost planar, the dihedral angle between the two benzene rings being 4.32 (8)°. The two hy-droxy substit-uents are coplanar with each of their attached benzene rings [r.m.s. deviations of 0.0053 (2) and 0.0052 (2) Å]. An intra-molecular N-H⋯O hydrogen bond formed between the iminium N and the phenolate O atom generates an S(6) ring motif. In the crystal, the mol-ecules are linked through O-H⋯O hydrogen bonds into chains along [110]. Two neighbouring chains are further connected through O-H⋯O hydrogen bonds in an anti-parallel manner. π-π inter-actions are also observed, with centroid-centroid distances of 3.7115 (19) and 3.743 (2) Å.

Related literature

For background to Schiff bases and their applications, see: Dao et al. (2000 ▶); Kagkelari et al. (2009 ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶). For related structures, see: Eltayeb et al. (2009 ▶, 2010a ▶,b ▶); Tan & Liu (2009 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H11NO3

M = 229.23

Monoclinic,

a = 11.048 (5) Å

b = 8.187 (3) Å

c = 22.858 (10) Å

β = 102.242 (13)°

V = 2020.5 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.35 × 0.12 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.996

15107 measured reflections

2967 independent reflections

2122 reflections with I > 2σ(I)

R int = 0.087

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.173

S = 1.06

2967 reflections

198 parameters

All H-atom parameters refined

Δρmax = 0.48 e Å−3

Δρmin = −0.28 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020295/rz2453sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020295/rz2453Isup2.hkl

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

C13H11NO3	F(000) = 960
Mr = 229.23	Dx = 1.507 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2967 reflections
a = 11.048 (5) Å	θ = 1.8–30.1°
b = 8.187 (3) Å	µ = 0.11 mm−1
c = 22.858 (10) Å	T = 100 K
β = 102.242 (13)°	Plate, red
V = 2020.5 (15) Å3	0.35 × 0.12 × 0.04 mm
Z = 8

Bruker APEXII DUO CCD area-detector diffractometer	2967 independent reflections
Radiation source: sealed tube	2122 reflections with I > 2σ(I)
graphite	Rint = 0.087
φ and ω scans	θmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.963, Tmax = 0.996	k = −11→11
15107 measured reflections	l = −32→32

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	All H-atom parameters refined
S = 1.06	w = 1/[σ2(Fo2) + (0.1024P)2 + 0.2914P] where P = (Fo2 + 2Fc2)/3
2967 reflections	(Δ/σ)max = 0.001
198 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.33647 (12)	0.68246 (15)	0.56400 (5)	0.0181 (3)
H1O1	0.339 (3)	0.792 (4)	0.5686 (14)	0.049 (8)*
O2	0.19184 (11)	0.49929 (14)	0.43502 (5)	0.0172 (3)
O3	−0.15299 (12)	0.01393 (15)	0.36222 (6)	0.0195 (3)
H1O3	−0.212 (3)	0.001 (3)	0.3867 (14)	0.045 (8)*
N1	0.18126 (13)	0.43402 (17)	0.54431 (6)	0.0136 (3)
H1N1	0.213 (2)	0.484 (3)	0.5165 (12)	0.034 (7)*
C1	0.22799 (14)	0.47819 (19)	0.60450 (7)	0.0137 (3)
C2	0.30862 (15)	0.6115 (2)	0.61334 (7)	0.0147 (3)
C3	0.35926 (16)	0.6624 (2)	0.67122 (8)	0.0167 (3)
H3	0.413 (2)	0.755 (3)	0.6766 (10)	0.024 (6)*
C4	0.32876 (16)	0.5824 (2)	0.71942 (8)	0.0177 (3)
H4	0.363 (2)	0.614 (3)	0.7600 (11)	0.026 (6)*
C5	0.24766 (16)	0.4510 (2)	0.71042 (8)	0.0178 (3)
H5	0.227 (2)	0.393 (3)	0.7447 (11)	0.028 (6)*
C6	0.19743 (16)	0.3972 (2)	0.65277 (7)	0.0161 (3)
H6	0.1437 (19)	0.309 (3)	0.6478 (9)	0.016 (5)*
C7	0.09838 (15)	0.32381 (19)	0.52344 (7)	0.0142 (3)
H7	0.0643 (18)	0.254 (2)	0.5512 (9)	0.013 (5)*
C8	0.05807 (15)	0.29461 (19)	0.46077 (7)	0.0139 (3)
C9	0.10800 (15)	0.38498 (19)	0.41820 (7)	0.0139 (3)
C10	0.06509 (16)	0.3443 (2)	0.35726 (7)	0.0160 (3)
H10	0.101 (2)	0.405 (3)	0.3290 (11)	0.027 (6)*
C11	−0.02034 (15)	0.2222 (2)	0.34016 (7)	0.0156 (3)
H11	−0.049 (2)	0.192 (3)	0.2956 (11)	0.025 (6)*
C12	−0.06925 (15)	0.1342 (2)	0.38267 (7)	0.0144 (3)
C13	−0.03095 (15)	0.17081 (19)	0.44220 (7)	0.0146 (3)
H13	−0.066 (2)	0.111 (3)	0.4732 (10)	0.024 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0240 (7)	0.0158 (6)	0.0154 (6)	−0.0033 (5)	0.0063 (5)	0.0012 (4)
O2	0.0194 (6)	0.0153 (6)	0.0168 (6)	−0.0061 (5)	0.0040 (5)	−0.0009 (4)
O3	0.0194 (6)	0.0202 (6)	0.0198 (6)	−0.0099 (5)	0.0062 (5)	−0.0055 (5)
N1	0.0137 (6)	0.0136 (6)	0.0131 (6)	−0.0001 (5)	0.0018 (5)	0.0008 (5)
C1	0.0141 (7)	0.0136 (7)	0.0128 (7)	0.0030 (6)	0.0014 (6)	−0.0005 (5)
C2	0.0157 (7)	0.0140 (7)	0.0146 (7)	0.0013 (6)	0.0037 (6)	0.0021 (6)
C3	0.0169 (8)	0.0139 (7)	0.0182 (8)	−0.0009 (6)	0.0014 (6)	−0.0019 (6)
C4	0.0205 (8)	0.0174 (8)	0.0139 (7)	0.0026 (6)	0.0011 (6)	−0.0008 (6)
C5	0.0203 (8)	0.0185 (8)	0.0150 (7)	0.0031 (7)	0.0045 (6)	0.0021 (6)
C6	0.0168 (8)	0.0151 (8)	0.0163 (8)	−0.0005 (6)	0.0036 (6)	0.0016 (6)
C7	0.0134 (7)	0.0131 (7)	0.0164 (7)	0.0011 (6)	0.0037 (6)	0.0015 (6)
C8	0.0133 (7)	0.0130 (7)	0.0152 (7)	−0.0002 (6)	0.0025 (6)	−0.0010 (6)
C9	0.0119 (7)	0.0127 (7)	0.0172 (7)	0.0002 (6)	0.0032 (6)	−0.0001 (6)
C10	0.0176 (8)	0.0159 (7)	0.0153 (7)	−0.0014 (6)	0.0049 (6)	0.0010 (6)
C11	0.0143 (7)	0.0175 (7)	0.0151 (7)	0.0004 (6)	0.0035 (6)	−0.0011 (6)
C12	0.0125 (7)	0.0123 (7)	0.0183 (8)	−0.0021 (6)	0.0031 (6)	−0.0016 (6)
C13	0.0155 (7)	0.0134 (7)	0.0158 (7)	−0.0012 (6)	0.0052 (6)	0.0010 (6)

O1—C2	1.3608 (19)	C5—C6	1.389 (2)
O1—H1O1	0.91 (3)	C5—H5	0.98 (2)
O2—C9	1.316 (2)	C6—H6	0.93 (2)
O3—C12	1.364 (2)	C7—C8	1.427 (2)
O3—H1O3	0.95 (3)	C7—H7	0.99 (2)
N1—C7	1.302 (2)	C8—C13	1.413 (2)
N1—C1	1.410 (2)	C8—C9	1.423 (2)
N1—H1N1	0.89 (3)	C9—C10	1.413 (2)
C1—C6	1.389 (2)	C10—C11	1.373 (2)
C1—C2	1.396 (2)	C10—H10	0.97 (2)
C2—C3	1.387 (2)	C11—C12	1.406 (2)
C3—C4	1.383 (2)	C11—H11	1.03 (2)
C3—H3	0.96 (2)	C12—C13	1.370 (2)
C4—C5	1.387 (3)	C13—H13	1.00 (2)
C4—H4	0.96 (2)
C2—O1—H1O1	109.4 (19)	C1—C6—H6	122.1 (13)
C12—O3—H1O3	112.0 (17)	N1—C7—C8	121.96 (15)
C7—N1—C1	128.22 (15)	N1—C7—H7	120.0 (12)
C7—N1—H1N1	114.2 (17)	C8—C7—H7	118.0 (12)
C1—N1—H1N1	117.6 (17)	C13—C8—C9	120.89 (14)
C6—C1—C2	120.88 (14)	C13—C8—C7	118.07 (14)
C6—C1—N1	123.52 (15)	C9—C8—C7	121.02 (15)
C2—C1—N1	115.60 (14)	O2—C9—C10	121.61 (14)
O1—C2—C3	123.09 (15)	O2—C9—C8	121.39 (14)
O1—C2—C1	117.61 (14)	C10—C9—C8	116.99 (15)
C3—C2—C1	119.28 (15)	C11—C10—C9	121.25 (15)
C4—C3—C2	120.03 (16)	C11—C10—H10	122.8 (14)
C4—C3—H3	121.6 (14)	C9—C10—H10	116.0 (14)
C2—C3—H3	118.3 (14)	C10—C11—C12	121.19 (15)
C3—C4—C5	120.51 (15)	C10—C11—H11	120.5 (12)
C3—C4—H4	122.0 (14)	C12—C11—H11	118.3 (12)
C5—C4—H4	117.5 (14)	O3—C12—C13	122.86 (14)
C4—C5—C6	120.17 (16)	O3—C12—C11	117.72 (15)
C4—C5—H5	120.3 (14)	C13—C12—C11	119.42 (15)
C6—C5—H5	119.5 (14)	C12—C13—C8	120.25 (14)
C5—C6—C1	119.12 (16)	C12—C13—H13	120.8 (13)
C5—C6—H6	118.8 (13)	C8—C13—H13	119.0 (13)
C7—N1—C1—C6	5.5 (3)	N1—C7—C8—C9	0.4 (2)
C7—N1—C1—C2	−174.41 (15)	C13—C8—C9—O2	−179.28 (14)
C6—C1—C2—O1	178.56 (15)	C7—C8—C9—O2	−0.7 (2)
N1—C1—C2—O1	−1.6 (2)	C13—C8—C9—C10	−0.4 (2)
C6—C1—C2—C3	0.5 (2)	C7—C8—C9—C10	178.20 (15)
N1—C1—C2—C3	−179.68 (14)	O2—C9—C10—C11	178.48 (15)
O1—C2—C3—C4	−178.66 (15)	C8—C9—C10—C11	−0.4 (2)
C1—C2—C3—C4	−0.7 (2)	C9—C10—C11—C12	0.6 (3)
C2—C3—C4—C5	0.0 (3)	C10—C11—C12—O3	−179.51 (15)
C3—C4—C5—C6	0.8 (3)	C10—C11—C12—C13	0.0 (2)
C4—C5—C6—C1	−1.0 (3)	O3—C12—C13—C8	178.68 (14)
C2—C1—C6—C5	0.4 (2)	C11—C12—C13—C8	−0.8 (2)
N1—C1—C6—C5	−179.48 (15)	C9—C8—C13—C12	1.0 (2)
C1—N1—C7—C8	178.69 (15)	C7—C8—C13—C12	−177.65 (15)
N1—C7—C8—C13	179.06 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2i	0.90 (3)	1.74 (3)	2.625 (2)	166 (3)
O3—H1O3···O2ii	0.95 (3)	1.69 (3)	2.633 (2)	173 (2)
N1—H1N1···O2	0.89 (3)	1.83 (3)	2.581 (2)	141 (2)
C13—H13···O1ii	1.00 (2)	2.60 (2)	3.411 (3)	137.8 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2i	0.90 (3)	1.74 (3)	2.625 (2)	166 (3)
O3—H1O3⋯O2ii	0.95 (3)	1.69 (3)	2.633 (2)	173 (2)
N1—H1N1⋯O2	0.89 (3)	1.83 (3)	2.581 (2)	141 (2)
C13—H13⋯O1ii	1.00 (2)	2.60 (2)	3.411 (3)	137.8 (18)

Symmetry codes: (i) ; (ii) .