2-Hy-droxy-5-{[(E)-4-meth-oxy-benzyl-idene]aza-nium-yl}benzoate.

In the title zwitterion, C(15)H(13)NO(4), obtained from the condensation of 5-amino-salicylic acid and 4-meth-oxy-benz-alde-hyde, the 4-hydoxyanilinic group of the 5-amino-salicylic acid moiety and the 4-meth-oxy-benzaldehyde moiety are twisted with respect to one another, making a dihedral angle of 10.37 (7)°. The carboxyl-ate group makes a dihedral angle of 5.7 (2)° with the parent 4-hydoxyanilinic group. An intra-molecular O-H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, inter-molecular C-H⋯O and N-H⋯O hydrogen bonds with R(2) (1)(7) ring motifs link the mol-ecules into infinite chains extending along the c axis. The occurence of slipped π-π stacking between symmetry-related aromatic rings reinforces the packing.

Related literature

For the related structures, see: Ashiq et al. (2010 ▶); Bryan et al. (1978 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For π–π stacking, see: Janiak (2000 ▶).

Experimental

Crystal data

C15H13NO4

M = 271.26

Monoclinic,

a = 13.4369 (12) Å

b = 8.5619 (8) Å

c = 12.6653 (11) Å

β = 118.004 (3)°

V = 1286.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.26 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.982, T max = 0.987

9561 measured reflections

2320 independent reflections

1583 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.143

S = 1.02

2320 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 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 datablocks global, I. DOI: 10.1107/S1600536810036172/dn2599sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036172/dn2599Isup2.hkl

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

C15H13NO4	F(000) = 568
Mr = 271.26	Dx = 1.401 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1583 reflections
a = 13.4369 (12) Å	θ = 2.9–25.3°
b = 8.5619 (8) Å	µ = 0.10 mm−1
c = 12.6653 (11) Å	T = 296 K
β = 118.004 (3)°	Prism, light brown
V = 1286.5 (2) Å3	0.26 × 0.20 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2320 independent reflections
Radiation source: fine-focus sealed tube	1583 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.9°
ω scans	h = −15→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.982, Tmax = 0.987	l = −15→10
9561 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0831P)2 + 0.1187P] where P = (Fo2 + 2Fc2)/3
2320 reflections	(Δ/σ)max < 0.001
182 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.18 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 > 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	−0.19046 (12)	0.62390 (19)	0.15961 (12)	0.0667 (5)
O2	−0.03306 (11)	0.49725 (16)	0.27753 (10)	0.0510 (4)
O3	−0.29868 (11)	0.56256 (18)	−0.05677 (12)	0.0613 (5)
H3	−0.2728	0.6015	0.0176	0.092*
O4	0.50744 (13)	−0.1897 (2)	0.09919 (15)	0.0857 (6)
N1	0.04782 (11)	0.17725 (17)	−0.01733 (13)	0.0405 (4)
H1	0.0329	0.1255	−0.0813	0.049*
C1	−0.11320 (15)	0.5260 (2)	0.17761 (15)	0.0406 (5)
C2	−0.11993 (13)	0.4447 (2)	0.06936 (14)	0.0353 (4)
C3	−0.21322 (15)	0.4691 (2)	−0.04323 (16)	0.0437 (5)
C4	−0.21754 (16)	0.3965 (3)	−0.14312 (17)	0.0548 (6)
H4	−0.2793	0.4128	−0.2178	0.066*
C5	−0.13155 (15)	0.3009 (2)	−0.13273 (16)	0.0507 (5)
H5	−0.1350	0.2530	−0.2002	0.061*
C6	−0.03929 (14)	0.2756 (2)	−0.02139 (15)	0.0382 (4)
C7	−0.03399 (13)	0.3462 (2)	0.07921 (15)	0.0371 (4)
H7	0.0273	0.3276	0.1537	0.044*
C8	0.14683 (14)	0.1574 (2)	0.07203 (16)	0.0421 (5)
H8	0.1627	0.2105	0.1423	0.051*
C9	0.23438 (14)	0.0614 (2)	0.07311 (16)	0.0413 (5)
C10	0.33683 (16)	0.0561 (3)	0.17828 (17)	0.0548 (6)
H10	0.3447	0.1116	0.2449	0.066*
C11	0.42584 (16)	−0.0289 (3)	0.18534 (18)	0.0633 (7)
H11	0.4934	−0.0315	0.2562	0.076*
C12	0.41467 (16)	−0.1115 (3)	0.08600 (18)	0.0547 (6)
C13	0.31336 (17)	−0.1093 (3)	−0.01877 (18)	0.0541 (5)
H13	0.3056	−0.1665	−0.0846	0.065*
C14	0.22442 (16)	−0.0231 (2)	−0.02569 (17)	0.0476 (5)
H14	0.1570	−0.0209	−0.0967	0.057*
C15	0.5007 (2)	−0.2741 (4)	−0.0010 (3)	0.1025 (10)
H15A	0.5716	−0.3243	0.0206	0.154*
H15B	0.4836	−0.2032	−0.0660	0.154*
H15C	0.4424	−0.3515	−0.0250	0.154*

	U11	U22	U33	U12	U13	U23
O1	0.0623 (9)	0.0904 (12)	0.0448 (8)	0.0283 (9)	0.0230 (7)	−0.0037 (8)
O2	0.0533 (8)	0.0604 (9)	0.0315 (7)	0.0028 (7)	0.0135 (6)	0.0023 (6)
O3	0.0447 (8)	0.0827 (11)	0.0461 (8)	0.0220 (7)	0.0127 (7)	−0.0035 (7)
O4	0.0628 (10)	0.1237 (15)	0.0748 (11)	0.0473 (10)	0.0358 (9)	0.0216 (11)
N1	0.0403 (8)	0.0448 (9)	0.0360 (8)	0.0020 (7)	0.0176 (7)	−0.0029 (7)
C1	0.0401 (10)	0.0465 (11)	0.0365 (10)	−0.0018 (9)	0.0189 (9)	0.0033 (8)
C2	0.0337 (9)	0.0390 (10)	0.0332 (9)	−0.0022 (8)	0.0157 (8)	0.0026 (8)
C3	0.0361 (9)	0.0522 (12)	0.0392 (10)	0.0055 (9)	0.0147 (8)	0.0013 (9)
C4	0.0436 (11)	0.0728 (14)	0.0321 (10)	0.0118 (11)	0.0046 (9)	−0.0036 (10)
C5	0.0472 (11)	0.0620 (13)	0.0345 (10)	0.0066 (10)	0.0120 (9)	−0.0085 (9)
C6	0.0360 (9)	0.0402 (10)	0.0388 (10)	0.0019 (8)	0.0177 (8)	0.0009 (8)
C7	0.0320 (9)	0.0417 (10)	0.0332 (9)	−0.0005 (8)	0.0118 (8)	0.0050 (8)
C8	0.0408 (10)	0.0478 (11)	0.0362 (10)	−0.0014 (9)	0.0168 (8)	−0.0032 (8)
C9	0.0369 (10)	0.0465 (11)	0.0385 (10)	0.0012 (8)	0.0161 (8)	0.0009 (8)
C10	0.0445 (11)	0.0755 (15)	0.0372 (11)	0.0052 (10)	0.0131 (9)	−0.0055 (10)
C11	0.0399 (11)	0.0946 (18)	0.0445 (12)	0.0129 (11)	0.0108 (10)	0.0063 (12)
C12	0.0457 (11)	0.0698 (14)	0.0526 (13)	0.0199 (11)	0.0264 (10)	0.0174 (11)
C13	0.0569 (12)	0.0628 (13)	0.0435 (11)	0.0120 (11)	0.0243 (10)	0.0011 (10)
C14	0.0393 (10)	0.0557 (12)	0.0399 (10)	0.0071 (9)	0.0120 (9)	−0.0008 (9)
C15	0.103 (2)	0.123 (2)	0.107 (2)	0.0604 (19)	0.0700 (18)	0.0201 (19)

O1—C1	1.269 (2)	C6—C7	1.381 (2)
O2—C1	1.242 (2)	C7—H7	0.9300
O3—C3	1.343 (2)	C8—C9	1.430 (2)
O3—H3	0.9015	C8—H8	0.9300
O4—C12	1.354 (2)	C9—C10	1.396 (2)
O4—C15	1.426 (3)	C9—C14	1.396 (3)
N1—C8	1.291 (2)	C10—C11	1.367 (3)
N1—C6	1.423 (2)	C10—H10	0.9300
N1—H1	0.8600	C11—C12	1.389 (3)
C1—C2	1.502 (2)	C11—H11	0.9300
C2—C7	1.388 (2)	C12—C13	1.385 (3)
C2—C3	1.404 (2)	C13—C14	1.372 (3)
C3—C4	1.386 (3)	C13—H13	0.9300
C4—C5	1.371 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.390 (2)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C3—O3—H3	101.5	N1—C8—H8	117.0
C12—O4—C15	118.07 (18)	C9—C8—H8	117.0
C8—N1—C6	126.96 (16)	C10—C9—C14	118.36 (17)
C8—N1—H1	116.5	C10—C9—C8	117.77 (17)
C6—N1—H1	116.5	C14—C9—C8	123.85 (16)
O2—C1—O1	123.99 (17)	C11—C10—C9	121.33 (19)
O2—C1—C2	119.34 (16)	C11—C10—H10	119.3
O1—C1—C2	116.65 (15)	C9—C10—H10	119.3
C7—C2—C3	119.37 (16)	C10—C11—C12	119.54 (18)
C7—C2—C1	120.59 (15)	C10—C11—H11	120.2
C3—C2—C1	120.04 (15)	C12—C11—H11	120.2
O3—C3—C4	118.93 (16)	O4—C12—C13	124.0 (2)
O3—C3—C2	121.38 (16)	O4—C12—C11	115.99 (18)
C4—C3—C2	119.68 (16)	C13—C12—C11	120.05 (18)
C5—C4—C3	120.52 (17)	C14—C13—C12	120.22 (19)
C5—C4—H4	119.7	C14—C13—H13	119.9
C3—C4—H4	119.7	C12—C13—H13	119.9
C4—C5—C6	120.05 (17)	C13—C14—C9	120.49 (17)
C4—C5—H5	120.0	C13—C14—H14	119.8
C6—C5—H5	120.0	C9—C14—H14	119.8
C7—C6—C5	120.18 (16)	O4—C15—H15A	109.5
C7—C6—N1	122.70 (15)	O4—C15—H15B	109.5
C5—C6—N1	117.12 (16)	H15A—C15—H15B	109.5
C6—C7—C2	120.18 (15)	O4—C15—H15C	109.5
C6—C7—H7	119.9	H15A—C15—H15C	109.5
C2—C7—H7	119.9	H15B—C15—H15C	109.5
N1—C8—C9	126.07 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.90	1.62	2.4816 (19)	159
N1—H1···O2i	0.86	1.90	2.7408 (19)	166
C8—H8···O1ii	0.93	2.47	3.179 (2)	133
C14—H14···O2i	0.93	2.30	3.183 (2)	159
C15—H15A···O3iii	0.96	2.56	3.393 (3)	145

Cg···Cg	centroid–centroid distance	mean interplanar distancea	slippage angleb
Cg1···Cg1i	3.7848 (13)	3.428 (1)	25.1
Cg1···Cg2ii	3.8456 (13)	3.567 (1)	22.0

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1	0.90	1.62	2.4816 (19)	159
N1—H1⋯O2i	0.86	1.90	2.7408 (19)	166
C8—H8⋯O1ii	0.93	2.47	3.179 (2)	133
C14—H14⋯O2i	0.93	2.30	3.183 (2)	159
C15—H15A⋯O3iii	0.96	2.56	3.393 (3)	145

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

Table 2

π–π stacking inter­actions (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C9–C14 rings, respectively.

Cg⋯Cg	centroid–centroid distance	mean inter­planar distancea	slippage angleb
Cg1⋯Cg1i	3.7848 (13)	3.428 (1)	25.1
Cg1⋯Cg2ii	3.8456 (13)	3.567 (1)	22.0

Symmetry codes: (i) −x, 1 − y, −z, (ii) −x, −y, −z. Notes: (a) distance from one plane to the neighbouring centroid; (b) angle subtended by the inter­centroid vector to the plane normal. For details, see: Janiak (2000 ▶).