(E)-3-[(3-Eth-oxy-2-hy-droxy-benzyl-idene)amino]-benzoic acid.

In the title compound, C(16)H(15)NO(4), a potential bidentate N,O-donor Schiff base ligand, the benzene rings are inclined to one another by 4.24 (12)°. The mol-ecule has an E conformation about the C=N bond. An intra-molecular O-H⋯N hydrogen bond makes an S(6) ring motif. In the crystal, pairs of O-H⋯O hydrogen bonds link the mol-ecules, forming inversion dimers with R(2) (2)(8) ring motifs. These dimers are further connected by C-H⋯O inter-actions, forming a sheet in (104). There is also a C-H⋯π inter-action present involving neighbouring mol-ecules.

Related literature

For background to Schiff bases ligands and their metal complexes, see: Kargar et al. (2011 ▶, 2012 ▶); Kia et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H15NO4

M = 285.29

Triclinic,

a = 5.0306 (3) Å

b = 7.1847 (4) Å

c = 19.6856 (13) Å

α = 94.956 (4)°

β = 93.310 (4)°

γ = 102.299 (4)°

V = 690.45 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.22 × 0.12 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.979, T max = 0.992

11954 measured reflections

3331 independent reflections

1429 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.150

S = 0.95

3331 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009968/su2387sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009968/su2387Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009968/su2387Isup3.cml

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

C16H15NO4	Z = 2
Mr = 285.29	F(000) = 300
Triclinic, P1	Dx = 1.372 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0306 (3) Å	Cell parameters from 2760 reflections
b = 7.1847 (4) Å	θ = 2.6–27.7°
c = 19.6856 (13) Å	µ = 0.10 mm−1
α = 94.956 (4)°	T = 296 K
β = 93.310 (4)°	Block, pale-yellow
γ = 102.299 (4)°	0.22 × 0.12 × 0.08 mm
V = 690.45 (7) Å3

Bruker SMART APEXII CCD area-detector diffractometer	3331 independent reflections
Radiation source: fine-focus sealed tube	1429 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.058
φ and ω scans	θmax = 28.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.979, Tmax = 0.992	k = −9→9
11954 measured reflections	l = −25→25

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0577P)2] where P = (Fo2 + 2Fc2)/3
3331 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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
C1	−0.7756 (4)	0.3599 (4)	0.95116 (13)	0.0401 (6)
C2	−0.6137 (4)	0.2435 (3)	0.91234 (12)	0.0381 (6)
C3	−0.6380 (5)	0.0522 (3)	0.92180 (13)	0.0491 (7)
H3B	−0.7556	−0.0044	0.9526	0.059*
C4	−0.4873 (5)	−0.0532 (4)	0.88541 (14)	0.0581 (8)
H4A	−0.5024	−0.1818	0.8916	0.070*
C5	−0.3131 (5)	0.0305 (4)	0.83961 (13)	0.0514 (7)
H5A	−0.2132	−0.0429	0.8149	0.062*
C6	−0.2848 (5)	0.2212 (4)	0.82988 (12)	0.0394 (6)
C7	−0.4376 (5)	0.3274 (3)	0.86627 (12)	0.0419 (6)
H7A	−0.4226	0.4559	0.8599	0.050*
C8	−0.0261 (5)	0.4639 (4)	0.77162 (12)	0.0450 (7)
H8A	−0.1074	0.5525	0.7949	0.054*
C9	0.1761 (4)	0.5293 (3)	0.72375 (12)	0.0404 (6)
C10	0.3028 (5)	0.3975 (3)	0.68892 (13)	0.0418 (6)
C11	0.4947 (5)	0.4626 (4)	0.64210 (13)	0.0461 (7)
C12	0.5568 (5)	0.6515 (4)	0.63127 (13)	0.0515 (7)
H12A	0.6851	0.6933	0.6006	0.062*
C13	0.4304 (5)	0.7824 (4)	0.66551 (14)	0.0559 (8)
H13A	0.4725	0.9106	0.6574	0.067*
C14	0.2425 (5)	0.7208 (4)	0.71145 (13)	0.0516 (7)
H14A	0.1590	0.8084	0.7346	0.062*
C15	0.7861 (5)	0.3715 (4)	0.55931 (14)	0.0554 (8)
H15A	0.9426	0.4700	0.5781	0.067*
H15B	0.6947	0.4196	0.5221	0.067*
C16	0.8758 (6)	0.1926 (4)	0.53405 (16)	0.0740 (9)
H16A	1.0043	0.2217	0.5002	0.111*
H16B	0.7201	0.0979	0.5142	0.111*
H16C	0.9603	0.1441	0.5717	0.111*
N1	−0.0939 (4)	0.2889 (3)	0.78237 (10)	0.0452 (6)
O1	−0.9217 (3)	0.2754 (2)	0.99589 (9)	0.0551 (5)
H1A	−1.0308	0.3568	1.0191	0.083*
O2	−0.7718 (3)	0.5279 (2)	0.93998 (9)	0.0527 (5)
O3	0.2460 (3)	0.2104 (2)	0.69762 (9)	0.0583 (5)
H3A	0.0815	0.1769	0.7229	0.087*
O4	0.6037 (4)	0.3213 (2)	0.61093 (9)	0.0613 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0324 (14)	0.0490 (16)	0.0379 (16)	0.0025 (11)	0.0121 (11)	0.0089 (12)
C2	0.0340 (14)	0.0450 (16)	0.0359 (16)	0.0074 (11)	0.0103 (11)	0.0064 (12)
C3	0.0483 (16)	0.0466 (17)	0.0541 (19)	0.0064 (12)	0.0205 (13)	0.0137 (14)
C4	0.0690 (19)	0.0396 (16)	0.071 (2)	0.0141 (14)	0.0290 (16)	0.0115 (14)
C5	0.0498 (16)	0.0517 (18)	0.056 (2)	0.0152 (13)	0.0189 (13)	0.0039 (14)
C6	0.0334 (13)	0.0479 (16)	0.0394 (16)	0.0106 (11)	0.0117 (11)	0.0085 (12)
C7	0.0420 (14)	0.0428 (15)	0.0440 (17)	0.0104 (11)	0.0149 (12)	0.0104 (12)
C8	0.0422 (15)	0.0557 (18)	0.0397 (17)	0.0146 (12)	0.0152 (12)	0.0024 (13)
C9	0.0340 (14)	0.0496 (16)	0.0395 (17)	0.0100 (11)	0.0123 (11)	0.0058 (12)
C10	0.0374 (14)	0.0463 (17)	0.0442 (17)	0.0102 (12)	0.0107 (11)	0.0119 (13)
C11	0.0409 (15)	0.0562 (18)	0.0459 (18)	0.0161 (12)	0.0183 (12)	0.0077 (13)
C12	0.0415 (16)	0.0612 (19)	0.0542 (19)	0.0099 (13)	0.0232 (13)	0.0103 (14)
C13	0.0570 (18)	0.0477 (17)	0.064 (2)	0.0069 (13)	0.0199 (15)	0.0106 (15)
C14	0.0528 (17)	0.0498 (18)	0.054 (2)	0.0133 (13)	0.0196 (14)	0.0005 (14)
C15	0.0464 (16)	0.080 (2)	0.0456 (18)	0.0209 (14)	0.0204 (13)	0.0118 (15)
C16	0.068 (2)	0.084 (2)	0.073 (2)	0.0216 (17)	0.0306 (17)	−0.0062 (17)
N1	0.0406 (12)	0.0528 (15)	0.0460 (15)	0.0125 (10)	0.0169 (10)	0.0111 (11)
O1	0.0545 (11)	0.0557 (12)	0.0635 (13)	0.0175 (8)	0.0359 (9)	0.0186 (9)
O2	0.0548 (11)	0.0448 (11)	0.0638 (13)	0.0126 (8)	0.0298 (9)	0.0149 (9)
O3	0.0578 (12)	0.0537 (12)	0.0724 (15)	0.0200 (9)	0.0338 (10)	0.0179 (10)
O4	0.0587 (12)	0.0651 (12)	0.0676 (14)	0.0196 (9)	0.0376 (10)	0.0117 (10)

C1—O2	1.242 (3)	C10—O3	1.342 (2)
C1—O1	1.289 (3)	C10—C11	1.409 (3)
C1—C2	1.482 (3)	C11—C12	1.365 (3)
C2—C3	1.384 (3)	C11—O4	1.370 (3)
C2—C7	1.389 (3)	C12—C13	1.392 (3)
C3—C4	1.369 (3)	C12—H12A	0.9300
C3—H3B	0.9300	C13—C14	1.377 (3)
C4—C5	1.379 (3)	C13—H13A	0.9300
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.378 (3)	C15—O4	1.426 (3)
C5—H5A	0.9300	C15—C16	1.505 (3)
C6—C7	1.380 (3)	C15—H15A	0.9700
C6—N1	1.420 (3)	C15—H15B	0.9700
C7—H7A	0.9300	C16—H16A	0.9600
C8—N1	1.270 (3)	C16—H16B	0.9600
C8—C9	1.458 (3)	C16—H16C	0.9600
C8—H8A	0.9300	O1—H1A	0.9862
C9—C14	1.391 (3)	O3—H3A	0.9867
C9—C10	1.403 (3)
O2—C1—O1	122.6 (2)	C9—C10—C11	119.0 (2)
O2—C1—C2	121.30 (19)	C12—C11—O4	125.9 (2)
O1—C1—C2	116.1 (2)	C12—C11—C10	120.2 (2)
C3—C2—C7	120.1 (2)	O4—C11—C10	113.9 (2)
C3—C2—C1	120.2 (2)	C11—C12—C13	120.8 (2)
C7—C2—C1	119.7 (2)	C11—C12—H12A	119.6
C4—C3—C2	119.4 (2)	C13—C12—H12A	119.6
C4—C3—H3B	120.3	C14—C13—C12	119.6 (2)
C2—C3—H3B	120.3	C14—C13—H13A	120.2
C3—C4—C5	120.3 (2)	C12—C13—H13A	120.2
C3—C4—H4A	119.9	C13—C14—C9	120.9 (2)
C5—C4—H4A	119.9	C13—C14—H14A	119.6
C6—C5—C4	121.1 (2)	C9—C14—H14A	119.6
C6—C5—H5A	119.4	O4—C15—C16	107.0 (2)
C4—C5—H5A	119.4	O4—C15—H15A	110.3
C5—C6—C7	118.7 (2)	C16—C15—H15A	110.3
C5—C6—N1	114.9 (2)	O4—C15—H15B	110.3
C7—C6—N1	126.4 (2)	C16—C15—H15B	110.3
C6—C7—C2	120.4 (2)	H15A—C15—H15B	108.6
C6—C7—H7A	119.8	C15—C16—H16A	109.5
C2—C7—H7A	119.8	C15—C16—H16B	109.5
N1—C8—C9	121.7 (2)	H16A—C16—H16B	109.5
N1—C8—H8A	119.2	C15—C16—H16C	109.5
C9—C8—H8A	119.2	H16A—C16—H16C	109.5
C14—C9—C10	119.5 (2)	H16B—C16—H16C	109.5
C14—C9—C8	120.8 (2)	C8—N1—C6	123.1 (2)
C10—C9—C8	119.8 (2)	C1—O1—H1A	113.1
O3—C10—C9	122.6 (2)	C10—O3—H3A	110.9
O3—C10—C11	118.3 (2)	C11—O4—C15	117.80 (19)
O2—C1—C2—C3	−174.8 (2)	C14—C9—C10—C11	−0.1 (4)
O1—C1—C2—C3	4.2 (3)	C8—C9—C10—C11	179.1 (2)
O2—C1—C2—C7	5.1 (4)	O3—C10—C11—C12	179.4 (2)
O1—C1—C2—C7	−175.9 (2)	C9—C10—C11—C12	0.3 (4)
C7—C2—C3—C4	0.0 (4)	O3—C10—C11—O4	−0.6 (3)
C1—C2—C3—C4	179.9 (2)	C9—C10—C11—O4	−179.7 (2)
C2—C3—C4—C5	−0.1 (4)	O4—C11—C12—C13	179.3 (3)
C3—C4—C5—C6	0.6 (4)	C10—C11—C12—C13	−0.7 (4)
C4—C5—C6—C7	−0.9 (4)	C11—C12—C13—C14	0.7 (4)
C4—C5—C6—N1	178.6 (2)	C12—C13—C14—C9	−0.4 (4)
C5—C6—C7—C2	0.8 (4)	C10—C9—C14—C13	0.1 (4)
N1—C6—C7—C2	−178.7 (2)	C8—C9—C14—C13	−179.0 (2)
C3—C2—C7—C6	−0.3 (4)	C9—C8—N1—C6	178.4 (2)
C1—C2—C7—C6	179.8 (2)	C5—C6—N1—C8	−173.9 (2)
N1—C8—C9—C14	178.4 (2)	C7—C6—N1—C8	5.6 (4)
N1—C8—C9—C10	−0.7 (4)	C12—C11—O4—C15	−4.1 (4)
C14—C9—C10—O3	−179.1 (2)	C10—C11—O4—C15	175.9 (2)
C8—C9—C10—O3	0.0 (4)	C16—C15—O4—C11	179.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N1	0.99	1.75	2.570 (3)	138
O1—H1A···O2i	0.99	1.63	2.610 (2)	174
C3—H3B···O1ii	0.93	2.58	3.453 (3)	157
C4—H4A···O2iii	0.93	2.53	3.341 (3)	146
C15—H15A···Cg2iv	0.97	2.75	3.610 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N1	0.99	1.75	2.570 (3)	138
O1—H1A⋯O2i	0.99	1.63	2.610 (2)	174
C3—H3B⋯O1ii	0.93	2.58	3.453 (3)	157
C4—H4A⋯O2iii	0.93	2.53	3.341 (3)	146
C15—H15A⋯Cg2iv	0.97	2.75	3.610 (3)	148

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