Crystal structure of (E)-4-hy-droxy-3-{1-[(4-hy-droxy-phen-yl)imino]-eth-yl}-6-methyl-2H-pyran-2-one.

In the title Schiff base, C14H13NO4, which adopts the phenol-imine tautomeric form, the dihedral angle between the planes of the benzene and heterocyclic (r.m.s. deviation = 0.037 Å) rings is 53.31 (11)°. An intra-molecular O-H⋯N hydrogen bond closes an S(6) ring. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds to generate C(11) chains propagating in the [010] direction. A weak C-H⋯O link is also observed, leading to the formation of R (5) 5(32) rings extending parallel to the (101) plane.

Related literature

For photochromic and thermochromic properties of hy­droxy Schiff bases, see: Garnovskii et al. (1993 ▸); Hadjoudis et al. (2004 ▸). For potential materials for optical memory and switch devices, see: Zhao et al. (2007 ▸). For proton-transfer processes, see: Lussier et al. (1987 ▸). For Schiff base structures, see: Djedouani et al. (2007 ▸, 2008 ▸). For Schiff base bond lengths and angles, see: Girija & Begum (2004 ▸); Girija et al. (2004 ▸); Bai & Jing (2007 ▸).

Experimental

Crystal data

C14H13NO4

M = 259.26

Monoclinic,

a = 7.8730 (5) Å

b = 11.7930 (8) Å

c = 13.5330 (8) Å

β = 99.896 (2)°

V = 1237.79 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.10 × 0.06 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▸) T min = 0.875, T max = 0.947

17976 measured reflections

2582 independent reflections

2061 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.148

S = 1.07

2582 reflections

173 parameters

All H-atom parameters refined

Δρmax = 0.54 e Å−3

Δρmin = −0.38 e Å−3

Data collection: COLLECT (Nonius, 2002 ▸); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▸); data reduction: EVALCCD (Duisenberg et al., 2003 ▸); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: OLEX2.refine (Dolomanov et al., 2009 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2006 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and PARST (Nardelli, 1995 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015012840/hb7460sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012840/hb7460Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012840/hb7460Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012840/hb7460fig1.tif

The structure of the title compound in 50% probability ellipsoids.

Click here for additional data file.

S . DOI: 10.1107/S2056989015012840/hb7460fig2.tif

Part of the crystal structure of (I), showing the formation of S(6) rings with dashed red lines. N—H⋯O and O—H⋯O hydrogen bonds are shown as blue dashed lines.

CCDC reference: 1410367

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

C14H13NO4	F(000) = 544.3271
Mr = 259.26	Dx = 1.391 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 0 reflections
a = 7.8730 (5) Å	θ = 2.9–27.5°
b = 11.7930 (8) Å	µ = 0.10 mm−1
c = 13.5330 (8) Å	T = 293 K
β = 99.896 (2)°	Block, yellow
V = 1237.79 (14) Å3	0.10 × 0.06 × 0.03 mm
Z = 4

Nonius KappaCCD diffractometer	2582 independent reflections
Radiation source: Enraf–Nonius FR590	2061 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 9 pixels mm-1	θmax = 26.7°, θmin = 2.3°
CCD rotation images, thin slices scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −14→14
Tmin = 0.875, Tmax = 0.947	l = −17→17
17976 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	All H-atom parameters refined
S = 1.07	w = 1/[σ2(Fo2) + (0.0655P)2 + 0.6848P] where P = (Fo2 + 2Fc2)/3
2582 reflections	(Δ/σ)max = 0.005
173 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.6637 (2)	−0.08723 (12)	0.50633 (10)	0.0520 (4)
H1	0.6696 (2)	−0.05535 (12)	0.45317 (10)	0.0779 (6)*
O2	0.4993 (2)	0.21003 (13)	−0.00201 (10)	0.0543 (4)
H2	0.4624 (2)	0.27519 (13)	−0.00450 (10)	0.0815 (7)*
O3	1.0343 (3)	0.20593 (17)	0.65333 (13)	0.0814 (7)
O4	0.92760 (19)	0.08216 (12)	0.74439 (9)	0.0443 (4)
C1	0.6821 (3)	0.11371 (17)	0.29043 (13)	0.0390 (4)
C2	0.7568 (3)	−0.07161 (18)	0.67874 (15)	0.0444 (5)
H2a	0.7031 (3)	−0.13959 (18)	0.68968 (15)	0.0533 (6)*
C3	0.6279 (3)	0.07382 (18)	0.11415 (14)	0.0433 (5)
H3	0.6333 (3)	0.02421 (18)	0.06136 (14)	0.0520 (6)*
C4	0.7488 (3)	−0.03156 (16)	0.57810 (14)	0.0391 (4)
C5	0.8305 (3)	0.12191 (16)	0.46720 (14)	0.0382 (4)
C6	0.6138 (3)	0.22135 (17)	0.27136 (14)	0.0416 (5)
H6	0.6089 (3)	0.27092 (17)	0.32425 (14)	0.0499 (6)*
C7	0.5531 (3)	0.25514 (17)	0.17428 (14)	0.0416 (5)
H7	0.5074 (3)	0.32751 (17)	0.16191 (14)	0.0499 (6)*
C8	0.8390 (3)	−0.01396 (17)	0.75665 (14)	0.0407 (5)
C9	0.9259 (3)	0.22691 (19)	0.44950 (16)	0.0489 (5)
H9a	0.9215 (18)	0.2372 (8)	0.37874 (17)	0.0733 (8)*
H9b	0.8738 (13)	0.2909 (3)	0.4764 (11)	0.0733 (8)*
H9c	1.0438 (6)	0.2203 (6)	0.4820 (10)	0.0733 (8)*
C10	0.5598 (3)	0.18172 (17)	0.09476 (13)	0.0389 (4)
C11	0.9398 (3)	0.12553 (18)	0.65006 (15)	0.0454 (5)
C12	0.8492 (3)	−0.0416 (2)	0.86465 (15)	0.0554 (6)
H12a	0.9678 (4)	−0.0434 (15)	0.8967 (3)	0.0831 (9)*
H12b	0.789 (2)	0.0151 (9)	0.8959 (3)	0.0831 (9)*
H12c	0.797 (2)	−0.1144 (7)	0.87109 (15)	0.0831 (9)*
C13	0.6877 (3)	0.03998 (17)	0.21150 (15)	0.0419 (5)
H13	0.7319 (3)	−0.03271 (17)	0.22414 (15)	0.0502 (6)*
C14	0.8397 (2)	0.07122 (16)	0.56378 (13)	0.0368 (4)
N1	0.7321 (2)	0.07168 (14)	0.39048 (12)	0.0434 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0748 (11)	0.0408 (8)	0.0347 (7)	−0.0120 (7)	−0.0066 (7)	0.0022 (6)
O2	0.0822 (11)	0.0507 (9)	0.0265 (7)	0.0122 (8)	−0.0009 (7)	0.0018 (6)
O3	0.1131 (16)	0.0775 (13)	0.0444 (9)	−0.0536 (12)	−0.0125 (9)	0.0064 (9)
O4	0.0563 (9)	0.0434 (8)	0.0295 (7)	−0.0021 (6)	−0.0029 (6)	−0.0003 (6)
C1	0.0454 (11)	0.0404 (10)	0.0286 (9)	−0.0016 (8)	−0.0009 (7)	0.0027 (8)
C2	0.0565 (13)	0.0373 (10)	0.0383 (10)	−0.0024 (9)	0.0051 (9)	0.0042 (8)
C3	0.0508 (12)	0.0445 (11)	0.0329 (10)	0.0055 (9)	0.0021 (8)	−0.0065 (8)
C4	0.0466 (11)	0.0347 (10)	0.0332 (9)	0.0032 (8)	−0.0009 (8)	−0.0006 (8)
C5	0.0431 (10)	0.0367 (10)	0.0329 (9)	0.0046 (8)	0.0012 (8)	0.0004 (8)
C6	0.0557 (12)	0.0394 (10)	0.0290 (9)	0.0000 (9)	0.0052 (8)	−0.0029 (8)
C7	0.0532 (12)	0.0359 (10)	0.0343 (10)	0.0040 (9)	0.0036 (8)	0.0028 (8)
C8	0.0475 (11)	0.0389 (10)	0.0346 (10)	0.0077 (8)	0.0046 (8)	0.0027 (8)
C9	0.0536 (13)	0.0506 (12)	0.0397 (11)	−0.0060 (10)	0.0007 (9)	0.0079 (9)
C10	0.0451 (11)	0.0425 (11)	0.0275 (9)	0.0004 (8)	0.0018 (7)	0.0032 (8)
C11	0.0555 (13)	0.0423 (11)	0.0348 (10)	−0.0052 (10)	−0.0028 (9)	0.0032 (8)
C12	0.0773 (16)	0.0557 (14)	0.0329 (11)	0.0044 (12)	0.0088 (10)	0.0034 (9)
C13	0.0462 (11)	0.0379 (10)	0.0385 (10)	0.0066 (8)	−0.0008 (8)	0.0005 (8)
C14	0.0439 (11)	0.0336 (9)	0.0306 (9)	0.0029 (8)	−0.0002 (8)	0.0021 (7)
N1	0.0560 (10)	0.0414 (9)	0.0290 (8)	−0.0014 (8)	−0.0033 (7)	0.0036 (7)

O1—H1	0.82	C5—C9	1.489 (3)
O1—C4	1.265 (2)	C5—C14	1.428 (3)
O2—H2	0.82	C5—N1	1.324 (2)
O2—C10	1.356 (2)	C6—H6	0.93
O3—C11	1.201 (3)	C6—C7	1.377 (3)
O4—C8	1.356 (2)	C7—H7	0.93
O4—C11	1.394 (2)	C7—C10	1.389 (3)
C1—C6	1.385 (3)	C8—C12	1.486 (3)
C1—C13	1.384 (3)	C9—H9a	0.96
C1—N1	1.432 (2)	C9—H9b	0.96
C2—H2a	0.93	C9—H9c	0.96
C2—C4	1.433 (3)	C11—C14	1.442 (3)
C2—C8	1.326 (3)	C12—H12a	0.96
C3—H3	0.93	C12—H12b	0.96
C3—C10	1.388 (3)	C12—H12c	0.96
C3—C13	1.380 (3)	C13—H13	0.93
C4—C14	1.438 (3)
C4—O1—H1	109.5	C12—C8—C2	127.3 (2)
C10—O2—H2	109.5	H9a—C9—C5	109.5
C11—O4—C8	122.46 (15)	H9b—C9—C5	109.5
C13—C1—C6	119.66 (17)	H9b—C9—H9a	109.5
N1—C1—C6	121.88 (17)	H9c—C9—C5	109.5
N1—C1—C13	118.18 (18)	H9c—C9—H9a	109.5
C4—C2—H2a	119.25 (12)	H9c—C9—H9b	109.5
C8—C2—H2a	119.25 (12)	C3—C10—O2	117.93 (17)
C8—C2—C4	121.5 (2)	C7—C10—O2	122.75 (18)
C10—C3—H3	119.90 (11)	C7—C10—C3	119.31 (17)
C13—C3—H3	119.90 (12)	O4—C11—O3	113.30 (18)
C13—C3—C10	120.19 (18)	C14—C11—O3	129.00 (19)
C2—C4—O1	119.33 (18)	C14—C11—O4	117.69 (18)
C14—C4—O1	122.99 (17)	H12a—C12—C8	109.5
C14—C4—C2	117.68 (17)	H12b—C12—C8	109.5
C14—C5—C9	123.23 (17)	H12b—C12—H12a	109.5
N1—C5—C9	119.29 (17)	H12c—C12—C8	109.5
N1—C5—C14	117.48 (18)	H12c—C12—H12a	109.5
H6—C6—C1	119.91 (11)	H12c—C12—H12b	109.5
C7—C6—C1	120.17 (18)	C3—C13—C1	120.30 (18)
C7—C6—H6	119.91 (12)	H13—C13—C1	119.85 (11)
H7—C7—C6	119.82 (12)	H13—C13—C3	119.85 (12)
C10—C7—C6	120.36 (18)	C5—C14—C4	121.89 (17)
C10—C7—H7	119.82 (11)	C11—C14—C4	118.74 (17)
C2—C8—O4	121.50 (18)	C11—C14—C5	119.35 (18)
C12—C8—O4	111.21 (18)	C5—N1—C1	127.99 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.83	2.560 (2)	147
O2—H2···O1i	0.82	1.90	2.710 (2)	169
C12—H12B···O3ii	0.96	2.55	3.137 (3)	120

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1N1	0.82	1.83	2.560(2)	147
O2H2O1i	0.82	1.90	2.710(2)	169
C12H12BO3ii	0.96	2.55	3.137(3)	120

Symmetry codes: (i) ; (ii) .