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

In the title compound, C(15)H(13)NO(4), the dihedral angle between the substituted benzene rings is 9.9 (8)°. Part of the mol-ecule (the salicylaldimine segment) is disordered over two sets of sites, with a refined site-occupancy ratio of 0.550 (14):0.450 (14). Intra-molecular O-H⋯N hydrogen bonds form S(6) ring motifs. In the crystal, pairs of O-H⋯O hydrogen bonds link mol-ecules into centrosymmetric dimers with R(2) (2)(8) ring motifs. The crystal packing also features C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C15H13NO4

M = 271.26

Triclinic,

a = 5.2738 (9) Å

b = 10.978 (2) Å

c = 12.084 (2) Å

α = 107.044 (10)°

β = 100.776 (11)°

γ = 97.539 (10)°

V = 644.1 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.19 × 0.12 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.981, T max = 0.991

8775 measured reflections

2308 independent reflections

1253 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.081

wR(F 2) = 0.258

S = 1.05

2308 reflections

279 parameters

405 restraints

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812010549/bq2344sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010549/bq2344Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010549/bq2344Isup3.cml

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

C15H13NO4	Z = 2
Mr = 271.26	F(000) = 284
Triclinic, P1	Dx = 1.399 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2738 (9) Å	Cell parameters from 1456 reflections
b = 10.978 (2) Å	θ = 2.8–28.8°
c = 12.084 (2) Å	µ = 0.10 mm−1
α = 107.044 (10)°	T = 296 K
β = 100.776 (11)°	Block, pale-yellow
γ = 97.539 (10)°	0.19 × 0.12 × 0.09 mm
V = 644.1 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2308 independent reflections
Radiation source: fine-focus sealed tube	1253 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 25.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.981, Tmax = 0.991	k = −13→13
8775 measured reflections	l = −14→14

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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.258	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1461P)2 + 0.0613P] where P = (Fo2 + 2Fc2)/3
2308 reflections	(Δ/σ)max < 0.001
279 parameters	Δρmax = 0.59 e Å−3
405 restraints	Δρmin = −0.28 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	Occ. (<1)
C1	0.2047 (6)	−0.0156 (3)	0.3825 (3)	0.0503 (9)
C2	0.3579 (6)	−0.0263 (3)	0.2901 (3)	0.0469 (8)
C3	0.3065 (7)	−0.1382 (3)	0.1929 (3)	0.0605 (10)
H3A	0.1755	−0.2078	0.1850	0.073*
C4	0.4508 (7)	−0.1461 (3)	0.1075 (3)	0.0659 (11)
H4A	0.4174	−0.2212	0.0421	0.079*
C5	0.6418 (7)	−0.0437 (3)	0.1192 (3)	0.0537 (9)
H5A	0.7389	−0.0505	0.0616	0.064*
C6	0.6948 (6)	0.0696 (3)	0.2142 (3)	0.0461 (8)
C7	0.5508 (6)	0.0785 (3)	0.3021 (3)	0.0472 (8)
H7A	0.5847	0.1537	0.3675	0.057*
O1	0.0350 (5)	−0.1160 (2)	0.3720 (2)	0.0663 (8)
O2	0.2431 (5)	0.0872 (2)	0.4652 (2)	0.0699 (8)
H2	0.1331	0.0870	0.5202	0.105*
N1	0.868 (3)	0.1754 (14)	0.215 (2)	0.038 (3)	0.550 (14)
C8	0.997 (2)	0.2711 (10)	0.3133 (11)	0.051 (3)	0.550 (14)
H8A	0.9624	0.2715	0.3861	0.061*	0.550 (14)
C9	1.192 (2)	0.3752 (9)	0.3088 (10)	0.054 (4)	0.550 (14)
C10	1.307 (8)	0.363 (2)	0.213 (3)	0.044 (5)	0.550 (14)
C11	1.473 (4)	0.4714 (14)	0.2060 (17)	0.058 (5)	0.550 (14)
C12	1.552 (7)	0.5805 (19)	0.305 (3)	0.062 (6)	0.550 (14)
H12A	1.6724	0.6497	0.3034	0.075*	0.550 (14)
C13	1.459 (2)	0.5914 (9)	0.4063 (10)	0.075 (3)	0.550 (14)
H13A	1.5152	0.6665	0.4722	0.090*	0.550 (14)
C14	1.281 (2)	0.4882 (9)	0.4072 (9)	0.073 (3)	0.550 (14)
H14A	1.2184	0.4940	0.4752	0.088*	0.550 (14)
C15	1.752 (2)	0.5546 (13)	0.0982 (14)	0.080 (4)	0.550 (14)
H15A	1.8146	0.5250	0.0272	0.121*	0.550 (14)
H15B	1.8972	0.5807	0.1667	0.121*	0.550 (14)
H15C	1.6696	0.6273	0.0964	0.121*	0.550 (14)
O3	1.207 (2)	0.2641 (12)	0.1078 (10)	0.065 (3)	0.550 (14)
H3	1.0896	0.2127	0.1154	0.097*	0.550 (14)
O4	1.565 (2)	0.4519 (10)	0.1044 (8)	0.080 (3)	0.550 (14)
N1A	0.929 (4)	0.1671 (17)	0.222 (3)	0.038 (3)	0.450 (14)
C8A	0.922 (2)	0.2889 (10)	0.2830 (11)	0.038 (3)	0.450 (14)
H8AA	0.7868	0.3062	0.3209	0.045*	0.450 (14)
C9A	1.128 (3)	0.3943 (10)	0.2899 (12)	0.044 (3)	0.450 (14)
C10A	1.287 (10)	0.374 (2)	0.210 (4)	0.041 (4)	0.450 (14)
C11A	1.503 (5)	0.4729 (15)	0.2231 (19)	0.044 (3)	0.450 (14)
C12A	1.521 (9)	0.595 (2)	0.300 (3)	0.062 (5)	0.450 (14)
H12B	1.6540	0.6625	0.3042	0.074*	0.450 (14)
C13A	1.344 (3)	0.6185 (9)	0.3695 (10)	0.061 (3)	0.450 (14)
H13B	1.3546	0.7023	0.4197	0.073*	0.450 (14)
C14A	1.151 (2)	0.5199 (7)	0.3662 (9)	0.057 (3)	0.450 (14)
H14B	1.0346	0.5371	0.4153	0.068*	0.450 (14)
C15A	1.854 (3)	0.5432 (16)	0.1425 (16)	0.077 (4)	0.450 (14)
H15D	1.9220	0.5133	0.0732	0.115*	0.450 (14)
H15E	1.9947	0.5697	0.2127	0.115*	0.450 (14)
H15F	1.7723	0.6156	0.1387	0.115*	0.450 (14)
O3A	1.295 (3)	0.2529 (14)	0.1380 (15)	0.062 (4)	0.450 (14)
H3B	1.1719	0.1997	0.1393	0.093*	0.450 (14)
O4A	1.661 (2)	0.4394 (11)	0.1466 (11)	0.062 (3)	0.450 (14)

	U11	U22	U33	U12	U13	U23
C1	0.049 (2)	0.0358 (17)	0.064 (2)	−0.0037 (15)	0.0263 (17)	0.0113 (16)
C2	0.0416 (18)	0.0415 (17)	0.061 (2)	0.0011 (15)	0.0226 (16)	0.0186 (16)
C3	0.058 (2)	0.0408 (18)	0.076 (2)	−0.0084 (16)	0.029 (2)	0.0086 (17)
C4	0.074 (3)	0.0459 (19)	0.069 (2)	−0.0080 (18)	0.035 (2)	0.0019 (17)
C5	0.054 (2)	0.0481 (19)	0.054 (2)	−0.0007 (16)	0.0273 (17)	0.0053 (16)
C6	0.0400 (18)	0.0430 (17)	0.057 (2)	0.0004 (14)	0.0226 (16)	0.0162 (15)
C7	0.0413 (18)	0.0389 (17)	0.059 (2)	−0.0023 (14)	0.0248 (16)	0.0097 (15)
O1	0.0638 (16)	0.0449 (13)	0.0852 (18)	−0.0150 (11)	0.0389 (14)	0.0117 (12)
O2	0.0772 (18)	0.0519 (15)	0.0748 (18)	−0.0139 (13)	0.0489 (14)	0.0046 (13)
N1	0.017 (7)	0.044 (2)	0.053 (3)	0.003 (3)	0.015 (5)	0.013 (2)
C8	0.045 (6)	0.055 (5)	0.046 (5)	−0.002 (4)	0.012 (4)	0.010 (4)
C9	0.048 (6)	0.050 (4)	0.057 (5)	0.001 (4)	0.025 (5)	0.003 (4)
C10	0.038 (8)	0.038 (6)	0.047 (5)	−0.002 (6)	0.014 (5)	0.002 (5)
C11	0.038 (6)	0.054 (5)	0.065 (7)	−0.007 (5)	0.025 (6)	−0.004 (5)
C12	0.045 (8)	0.051 (7)	0.080 (7)	−0.014 (7)	0.027 (6)	0.007 (6)
C13	0.058 (6)	0.057 (5)	0.082 (6)	−0.015 (4)	0.037 (5)	−0.018 (4)
C14	0.063 (6)	0.068 (5)	0.070 (5)	−0.015 (4)	0.038 (5)	−0.005 (4)
C15	0.057 (7)	0.079 (6)	0.105 (10)	−0.012 (5)	0.043 (7)	0.027 (6)
O3	0.057 (7)	0.052 (5)	0.067 (5)	−0.018 (4)	0.037 (5)	−0.009 (4)
O4	0.073 (6)	0.073 (4)	0.075 (5)	−0.030 (4)	0.040 (4)	0.004 (4)
N1A	0.017 (7)	0.044 (2)	0.053 (3)	0.003 (3)	0.015 (5)	0.013 (2)
C8A	0.027 (5)	0.042 (4)	0.047 (7)	0.008 (3)	0.021 (4)	0.010 (4)
C9A	0.040 (6)	0.034 (4)	0.057 (6)	0.000 (4)	0.020 (5)	0.013 (4)
C10A	0.030 (7)	0.033 (5)	0.062 (8)	0.004 (5)	0.021 (6)	0.013 (5)
C11A	0.042 (7)	0.042 (5)	0.054 (7)	0.001 (4)	0.017 (5)	0.023 (5)
C12A	0.055 (10)	0.044 (6)	0.077 (8)	−0.006 (6)	0.020 (7)	0.009 (6)
C13A	0.071 (7)	0.036 (4)	0.066 (6)	−0.004 (4)	0.022 (5)	0.005 (4)
C14A	0.060 (6)	0.039 (4)	0.070 (6)	0.006 (4)	0.028 (5)	0.010 (4)
C15A	0.067 (9)	0.069 (7)	0.099 (11)	−0.017 (7)	0.035 (7)	0.039 (7)
O3A	0.059 (8)	0.038 (4)	0.084 (8)	−0.002 (5)	0.041 (6)	0.002 (5)
O4A	0.050 (5)	0.064 (4)	0.076 (7)	−0.009 (4)	0.039 (5)	0.024 (4)

C1—O2	1.232 (4)	C13—C14	1.378 (9)
C1—O1	1.284 (4)	C13—H13A	0.9300
C1—C2	1.482 (5)	C14—H14A	0.9300
C2—C3	1.382 (4)	C15—O4	1.426 (9)
C2—C7	1.385 (4)	C15—H15A	0.9600
C3—C4	1.382 (5)	C15—H15B	0.9600
C3—H3A	0.9300	C15—H15C	0.9600
C4—C5	1.361 (4)	O3—H3	0.8200
C4—H4A	0.9300	N1A—C8A	1.333 (13)
C5—C6	1.376 (4)	C8A—C9A	1.450 (10)
C5—H5A	0.9300	C8A—H8AA	0.9300
C6—N1	1.38 (2)	C9A—C10A	1.382 (12)
C6—C7	1.405 (4)	C9A—C14A	1.391 (10)
C6—N1A	1.49 (3)	C10A—O3A	1.368 (19)
C7—H7A	0.9300	C10A—C11A	1.419 (14)
O2—H2	0.9612	C11A—O4A	1.362 (12)
N1—C8	1.329 (13)	C11A—C12A	1.367 (16)
C8—C9	1.454 (9)	C12A—C13A	1.374 (17)
C8—H8A	0.9300	C12A—H12B	0.9300
C9—C10	1.383 (11)	C13A—C14A	1.370 (10)
C9—C14	1.395 (9)	C13A—H13B	0.9300
C10—O3	1.365 (18)	C14A—H14B	0.9300
C10—C11	1.418 (13)	C15A—O4A	1.443 (10)
C11—C12	1.370 (15)	C15A—H15D	0.9600
C11—O4	1.373 (11)	C15A—H15E	0.9600
C12—C13	1.384 (16)	C15A—H15F	0.9600
C12—H12A	0.9300	O3A—H3B	0.8200
O2—C1—O1	122.7 (3)	C11—C12—H12A	118.8
O2—C1—C2	119.7 (3)	C13—C12—H12A	118.8
O1—C1—C2	117.6 (3)	C14—C13—C12	118.3 (8)
C3—C2—C7	120.6 (3)	C14—C13—H13A	120.9
C3—C2—C1	120.5 (3)	C12—C13—H13A	120.9
C7—C2—C1	118.9 (3)	C13—C14—C9	121.8 (7)
C2—C3—C4	119.7 (3)	C13—C14—H14A	119.1
C2—C3—H3A	120.2	C9—C14—H14A	119.1
C4—C3—H3A	120.2	C11—O4—C15	118.0 (9)
C5—C4—C3	120.0 (3)	C8A—N1A—C6	113.9 (18)
C5—C4—H4A	120.0	N1A—C8A—C9A	119.6 (14)
C3—C4—H4A	120.0	N1A—C8A—H8AA	120.2
C4—C5—C6	121.7 (3)	C9A—C8A—H8AA	120.2
C4—C5—H5A	119.2	C10A—C9A—C14A	118.6 (10)
C6—C5—H5A	119.2	C10A—C9A—C8A	119.5 (9)
C5—C6—N1	119.2 (10)	C14A—C9A—C8A	121.5 (10)
C5—C6—C7	118.9 (3)	O3A—C10A—C9A	123.2 (14)
N1—C6—C7	121.5 (9)	O3A—C10A—C11A	115 (2)
C5—C6—N1A	115.4 (10)	C9A—C10A—C11A	119.5 (10)
N1—C6—N1A	13.2 (17)	O4A—C11A—C12A	125.1 (11)
C7—C6—N1A	125.2 (11)	O4A—C11A—C10A	115.2 (10)
C2—C7—C6	119.2 (3)	C12A—C11A—C10A	119.3 (16)
C2—C7—H7A	120.4	C11A—C12A—C13A	120.0 (13)
C6—C7—H7A	120.4	C11A—C12A—H12B	120.0
C1—O2—H2	114.7	C13A—C12A—H12B	120.0
C8—N1—C6	123 (2)	C14A—C13A—C12A	120.9 (10)
N1—C8—C9	120.7 (14)	C14A—C13A—H13B	119.5
N1—C8—H8A	119.6	C12A—C13A—H13B	119.5
C9—C8—H8A	119.6	C13A—C14A—C9A	120.4 (9)
C10—C9—C14	118.3 (8)	C13A—C14A—H14B	119.8
C10—C9—C8	122.2 (8)	C9A—C14A—H14B	119.8
C14—C9—C8	119.4 (8)	O4A—C15A—H15D	109.5
O3—C10—C9	121.7 (12)	O4A—C15A—H15E	109.5
O3—C10—C11	115.0 (19)	H15D—C15A—H15E	109.5
C9—C10—C11	120.3 (8)	O4A—C15A—H15F	109.5
C12—C11—O4	125.4 (9)	H15D—C15A—H15F	109.5
C12—C11—C10	118.0 (14)	H15E—C15A—H15F	109.5
O4—C11—C10	116.1 (9)	C10A—O3A—H3B	109.5
C11—C12—C13	122.4 (10)	C11A—O4A—C15A	116.8 (11)
O2—C1—C2—C3	−176.1 (3)	O4—C11—C12—C13	−177 (3)
O1—C1—C2—C3	3.8 (5)	C10—C11—C12—C13	−5 (7)
O2—C1—C2—C7	3.1 (5)	C11—C12—C13—C14	0 (5)
O1—C1—C2—C7	−177.1 (3)	C12—C13—C14—C9	−1 (3)
C7—C2—C3—C4	0.6 (5)	C10—C9—C14—C13	7 (3)
C1—C2—C3—C4	179.8 (3)	C8—C9—C14—C13	−177.9 (9)
C2—C3—C4—C5	−0.2 (6)	C12—C11—O4—C15	−2 (4)
C3—C4—C5—C6	−0.7 (6)	C10—C11—O4—C15	−174 (3)
C4—C5—C6—N1	−172.3 (11)	C5—C6—N1A—C8A	156.3 (18)
C4—C5—C6—C7	1.2 (5)	N1—C6—N1A—C8A	46 (7)
C4—C5—C6—N1A	173.4 (14)	C7—C6—N1A—C8A	−32 (3)
C3—C2—C7—C6	−0.1 (5)	C6—N1A—C8A—C9A	−175.4 (16)
C1—C2—C7—C6	−179.3 (3)	N1A—C8A—C9A—C10A	17 (4)
C5—C6—C7—C2	−0.7 (5)	N1A—C8A—C9A—C14A	−170.5 (19)
N1—C6—C7—C2	172.6 (11)	C14A—C9A—C10A—O3A	175 (4)
N1A—C6—C7—C2	−172.2 (14)	C8A—C9A—C10A—O3A	−13 (7)
C5—C6—N1—C8	−157.2 (13)	C14A—C9A—C10A—C11A	13 (7)
C7—C6—N1—C8	29 (2)	C8A—C9A—C10A—C11A	−174 (4)
N1A—C6—N1—C8	−81 (10)	O3A—C10A—C11A—O4A	11 (6)
C6—N1—C8—C9	175.3 (12)	C9A—C10A—C11A—O4A	174 (4)
N1—C8—C9—C10	−19 (3)	O3A—C10A—C11A—C12A	−176 (4)
N1—C8—C9—C14	165.7 (13)	C9A—C10A—C11A—C12A	−13 (8)
C14—C9—C10—O3	−171 (3)	O4A—C11A—C12A—C13A	177 (3)
C8—C9—C10—O3	14 (5)	C10A—C11A—C12A—C13A	5 (8)
C14—C9—C10—C11	−12 (5)	C11A—C12A—C13A—C14A	2 (7)
C8—C9—C10—C11	173 (3)	C12A—C13A—C14A—C9A	−1 (3)
O3—C10—C11—C12	172 (4)	C10A—C9A—C14A—C13A	−6 (4)
C9—C10—C11—C12	11 (7)	C8A—C9A—C14A—C13A	−178.7 (11)
O3—C10—C11—O4	−16 (5)	C12A—C11A—O4A—C15A	−3 (5)
C9—C10—C11—O4	−176 (3)	C10A—C11A—O4A—C15A	169 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.96	1.69	2.638 (4)	169
O3—H3···N1	0.82	1.92	2.64 (2)	147
C15A—H15E···Cg1ii	0.96	2.90	3.757 (11)	139
C15A—H15E···Cg2ii	0.96	2.83	3.680 (12)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9–C14 and C9A–C14A rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.96	1.69	2.638 (4)	169
O3—H3⋯N1	0.82	1.92	2.64 (2)	147
C15A—H15E⋯Cg1ii	0.96	2.90	3.757 (11)	139
C15A—H15E⋯Cg2ii	0.96	2.83	3.680 (12)	139

Symmetry codes: (i) ; (ii) .