2-[(2-Hy-droxy-4-meth-oxy-benzyl-idene)aza-nium-yl]benzoate monohydrate.

In the title compound, C(15)H(13)NO(4)·H(2)O, the Schiff base exists in a zwitterionic form and a bifurcated intra-molecular N-H⋯(O,O) hydrogen bond generates two S(6) rings. The dihedral angle between the two benzene rings is 25.8 (2)°. The crystal structure is stabilized by inter-molecular O-H⋯O hydrogen bonds.

Related literature

For a related compound and background references to Schiff bases, see: Hang (2010 ▶). For related structures, see: Alpaslan et al. (2010a ▶,b ▶); Aritake et al. (2010 ▶); Bahron et al. (2010 ▶).

Experimental

Crystal data

C15H13NO4·H2O

M = 289.28

Triclinic,

a = 8.7240 (5) Å

b = 8.9252 (4) Å

c = 10.7967 (5) Å

α = 111.312 (2)°

β = 93.084 (3)°

γ = 117.500 (2)°

V = 669.24 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.30 × 0.28 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.968, T max = 0.970

4045 measured reflections

2810 independent reflections

1992 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.122

S = 1.08

2810 reflections

203 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023949/hb5506sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023949/hb5506Isup2.hkl

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

C15H13NO4·H2O	Z = 2
Mr = 289.28	F(000) = 304
Triclinic, P1	Dx = 1.436 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7240 (5) Å	Cell parameters from 1109 reflections
b = 8.9252 (4) Å	θ = 2.6–26.2°
c = 10.7967 (5) Å	µ = 0.11 mm−1
α = 111.312 (2)°	T = 298 K
β = 93.084 (3)°	Block, colorless
γ = 117.500 (2)°	0.30 × 0.28 × 0.28 mm
V = 669.24 (6) Å3

Bruker SMART CCD diffractometer	2810 independent reflections
Radiation source: fine-focus sealed tube	1992 reflections with I > 2σ(I)
graphite	Rint = 0.013
ω scans	θmax = 27.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→11
Tmin = 0.968, Tmax = 0.970	k = −11→11
4045 measured reflections	l = −13→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0595P)2 + 0.0161P] where P = (Fo2 + 2Fc2)/3
2810 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.15 e Å−3
5 restraints	Δρmin = −0.18 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
N1	0.91763 (18)	0.38037 (19)	0.21508 (14)	0.0364 (3)
O1	0.65275 (15)	0.22394 (15)	−0.01717 (12)	0.0446 (3)
O2	0.65944 (15)	0.04540 (16)	0.17602 (12)	0.0491 (3)
O3	0.65792 (17)	−0.01967 (18)	0.35525 (13)	0.0611 (4)
O4	0.59187 (15)	0.62901 (16)	−0.17000 (12)	0.0459 (3)
O5	0.68483 (19)	0.0450 (2)	0.63223 (16)	0.0715 (5)
C1	0.8648 (2)	0.5485 (2)	0.10069 (16)	0.0356 (4)
C2	0.7092 (2)	0.3956 (2)	−0.00735 (16)	0.0341 (4)
C3	0.6248 (2)	0.4303 (2)	−0.09650 (16)	0.0364 (4)
H3	0.5244	0.3306	−0.1682	0.044*
C4	0.6884 (2)	0.6120 (2)	−0.07994 (16)	0.0371 (4)
C5	0.8428 (2)	0.7642 (2)	0.02468 (18)	0.0431 (4)
H5	0.8866	0.8859	0.0346	0.052*
C6	0.9272 (2)	0.7302 (2)	0.11142 (18)	0.0430 (4)
H6	1.0301	0.8309	0.1805	0.052*
C7	0.9597 (2)	0.5313 (2)	0.19950 (17)	0.0377 (4)
H7	1.0645	0.6404	0.2605	0.045*
C8	1.0163 (2)	0.3714 (2)	0.31829 (16)	0.0371 (4)
C9	0.9308 (2)	0.2225 (2)	0.35416 (16)	0.0381 (4)
C10	1.0311 (2)	0.2180 (3)	0.45585 (19)	0.0486 (5)
H10	0.9764	0.1205	0.4813	0.058*
C11	1.2094 (3)	0.3539 (3)	0.5200 (2)	0.0542 (5)
H11	1.2743	0.3465	0.5865	0.065*
C12	1.2902 (2)	0.5003 (3)	0.48467 (19)	0.0520 (5)
H12	1.4098	0.5937	0.5289	0.062*
C13	1.1959 (2)	0.5100 (2)	0.38442 (18)	0.0449 (4)
H13	1.2520	0.6092	0.3608	0.054*
C14	0.7341 (2)	0.0706 (2)	0.29112 (17)	0.0408 (4)
C15	0.6600 (3)	0.8098 (3)	−0.1699 (2)	0.0545 (5)
H15A	0.6832	0.9017	−0.0787	0.082*
H15B	0.5730	0.8035	−0.2330	0.082*
H15C	0.7693	0.8447	−0.1978	0.082*
H5B	0.675 (3)	0.022 (3)	0.5468 (12)	0.080*
H5A	0.591 (2)	0.046 (3)	0.648 (2)	0.080*
H1	0.8112 (18)	0.2707 (19)	0.166 (2)	0.080*
H1A	0.5504 (18)	0.145 (3)	−0.0780 (19)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0349 (8)	0.0350 (8)	0.0348 (7)	0.0161 (6)	0.0043 (6)	0.0143 (6)
O1	0.0436 (7)	0.0320 (6)	0.0458 (7)	0.0131 (5)	−0.0044 (5)	0.0157 (5)
O2	0.0443 (7)	0.0412 (7)	0.0466 (7)	0.0112 (5)	−0.0061 (6)	0.0213 (6)
O3	0.0562 (8)	0.0592 (8)	0.0482 (8)	0.0121 (7)	0.0074 (6)	0.0288 (7)
O4	0.0474 (7)	0.0416 (7)	0.0490 (7)	0.0213 (6)	0.0037 (6)	0.0238 (6)
O5	0.0548 (9)	0.0918 (11)	0.0524 (9)	0.0265 (9)	0.0044 (7)	0.0331 (9)
C1	0.0335 (8)	0.0346 (9)	0.0336 (8)	0.0154 (7)	0.0053 (7)	0.0135 (7)
C2	0.0337 (8)	0.0306 (8)	0.0361 (9)	0.0151 (7)	0.0096 (7)	0.0148 (7)
C3	0.0325 (8)	0.0326 (8)	0.0355 (9)	0.0127 (7)	0.0043 (7)	0.0127 (7)
C4	0.0375 (9)	0.0389 (9)	0.0383 (9)	0.0203 (8)	0.0106 (7)	0.0196 (8)
C5	0.0433 (10)	0.0328 (9)	0.0494 (10)	0.0155 (8)	0.0090 (8)	0.0202 (8)
C6	0.0397 (9)	0.0320 (9)	0.0419 (10)	0.0098 (7)	0.0028 (7)	0.0137 (7)
C7	0.0339 (9)	0.0342 (9)	0.0366 (9)	0.0135 (7)	0.0056 (7)	0.0131 (7)
C8	0.0375 (9)	0.0398 (9)	0.0324 (8)	0.0225 (8)	0.0060 (7)	0.0114 (7)
C9	0.0403 (9)	0.0407 (9)	0.0338 (9)	0.0239 (8)	0.0072 (7)	0.0133 (7)
C10	0.0517 (11)	0.0553 (11)	0.0456 (10)	0.0313 (10)	0.0098 (8)	0.0246 (9)
C11	0.0513 (11)	0.0727 (13)	0.0441 (11)	0.0381 (11)	0.0041 (9)	0.0241 (10)
C12	0.0379 (10)	0.0631 (12)	0.0454 (11)	0.0255 (9)	0.0019 (8)	0.0164 (10)
C13	0.0374 (9)	0.0456 (10)	0.0439 (10)	0.0192 (8)	0.0061 (8)	0.0157 (8)
C14	0.0441 (10)	0.0373 (9)	0.0395 (9)	0.0207 (8)	0.0068 (8)	0.0163 (8)
C15	0.0688 (13)	0.0461 (11)	0.0553 (12)	0.0315 (10)	0.0085 (10)	0.0275 (9)

N1—C7	1.301 (2)	C5—C6	1.360 (2)
N1—C8	1.420 (2)	C5—H5	0.9300
N1—H1	0.912 (9)	C6—H6	0.9300
O1—C2	1.3346 (18)	C7—H7	0.9300
O1—H1A	0.863 (10)	C8—C13	1.393 (2)
O2—C14	1.2625 (19)	C8—C9	1.400 (2)
O3—C14	1.237 (2)	C9—C10	1.391 (2)
O4—C4	1.3474 (18)	C9—C14	1.517 (2)
O4—C15	1.438 (2)	C10—C11	1.379 (3)
O5—H5B	0.858 (9)	C10—H10	0.9300
O5—H5A	0.851 (9)	C11—C12	1.375 (3)
C1—C6	1.408 (2)	C11—H11	0.9300
C1—C7	1.410 (2)	C12—C13	1.377 (2)
C1—C2	1.424 (2)	C12—H12	0.9300
C2—C3	1.384 (2)	C13—H13	0.9300
C3—C4	1.384 (2)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.403 (2)	C15—H15C	0.9600
C7—N1—C8	125.26 (14)	C13—C8—C9	120.22 (15)
C7—N1—H1	121.8 (13)	C13—C8—N1	120.48 (15)
C8—N1—H1	112.5 (13)	C9—C8—N1	119.29 (14)
C2—O1—H1A	109.4 (15)	C10—C9—C8	117.87 (16)
C4—O4—C15	118.67 (13)	C10—C9—C14	118.71 (16)
H5B—O5—H5A	105.0 (17)	C8—C9—C14	123.39 (15)
C6—C1—C7	117.43 (14)	C11—C10—C9	121.89 (18)
C6—C1—C2	117.96 (14)	C11—C10—H10	119.1
C7—C1—C2	124.60 (14)	C9—C10—H10	119.1
O1—C2—C3	123.29 (14)	C12—C11—C10	119.34 (17)
O1—C2—C1	117.29 (14)	C12—C11—H11	120.3
C3—C2—C1	119.42 (14)	C10—C11—H11	120.3
C2—C3—C4	120.63 (14)	C11—C12—C13	120.63 (17)
C2—C3—H3	119.7	C11—C12—H12	119.7
C4—C3—H3	119.7	C13—C12—H12	119.7
O4—C4—C3	115.29 (14)	C12—C13—C8	120.03 (17)
O4—C4—C5	123.87 (14)	C12—C13—H13	120.0
C3—C4—C5	120.83 (14)	C8—C13—H13	120.0
C6—C5—C4	118.62 (15)	O3—C14—O2	124.52 (16)
C6—C5—H5	120.7	O3—C14—C9	118.27 (15)
C4—C5—H5	120.7	O2—C14—C9	117.21 (15)
C5—C6—C1	122.51 (15)	O4—C15—H15A	109.5
C5—C6—H6	118.7	O4—C15—H15B	109.5
C1—C6—H6	118.7	H15A—C15—H15B	109.5
N1—C7—C1	127.47 (15)	O4—C15—H15C	109.5
N1—C7—H7	116.3	H15A—C15—H15C	109.5
C1—C7—H7	116.3	H15B—C15—H15C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.91 (1)	2.14 (2)	2.7257 (17)	121 (2)
N1—H1···O2	0.91 (1)	1.88 (2)	2.6366 (17)	139 (2)
O1—H1A···O2i	0.86 (1)	1.72 (1)	2.5675 (16)	165 (2)
O5—H5A···O3ii	0.85 (1)	2.07 (1)	2.907 (2)	169 (2)
O5—H5B···O3	0.86 (1)	1.95 (1)	2.806 (2)	178 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.91 (1)	2.14 (2)	2.7257 (17)	121 (2)
N1—H1⋯O2	0.91 (1)	1.88 (2)	2.6366 (17)	139 (2)
O1—H1A⋯O2i	0.86 (1)	1.72 (1)	2.5675 (16)	165 (2)
O5—H5A⋯O3ii	0.85 (1)	2.07 (1)	2.907 (2)	169 (2)
O5—H5B⋯O3	0.86 (1)	1.95 (1)	2.806 (2)	178 (2)

Symmetry codes: (i) ; (ii) .