2-[(2-Hy­droxy-4-meth­oxy­benzyl­idene)aza­nium­yl]benzoate monohydrate

Hang, Z.-X.; Dong, B.; Wang, X.-W.

doi:10.1107/S1600536810023949

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1776

doi:10.1107/S1600536810023949

Open

access

2-[(2-Hydroxy-4-methoxybenzylidene)azaniumyl]benzoate monohydrate

Zhi-Xi Hang,^a ^* Bo Dong ^b and Xing-Wen Wang ^c

^aCollege of Biological and Chemical Engineering, Anhui Polytechnic University, Wuhu 241000, People's Republic of China, ^bCollege of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, People's Republic of China, and ^cDepartment of Biological and Enviromental Engineering, Hefei University, Hefei 230022, People's Republic of China
^*Correspondence e-mail: hangzhx@163.com

(Received 18 June 2010; accepted 20 June 2010; online 26 June 2010)

In the title compound, C₁₅H₁₃NO₄·H₂O, the Schiff base exists in a zwitterionic form and a bifurcated intramolecular 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 intermolecular 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_r = 289.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.122
S = 1.08
2810 reflections
203 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) -x+1, -y, -z; (ii) -x+1, -y, -z+1.

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.

Supporting information

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

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

checkCIF report

Comment top

The crystal structures of Schiff bases have been widely reported (Alpaslan et al., 2010a,b; Aritake et al., 2010; Bahron et al., 2010). As a continuation of our work on Schiff bases (Hang, 2010), the present paper reports the title Schiff base compound.

The title compound contains a Schiff base molecule and a water molecule of crystallization (Fig. 1). There exist two intramolecular N–H···O hydrogen bonds in the molecule of the compound. The dihedral angle between the two benzene rings is 25.8 (2)°. The crystal structure is stabilized by intermolecular O–H···O hydrogen bonds (Table 1, Fig. 2).

Related literature top

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 top

Equimolar quantities (1 mmol each) of 2-aminobenzoic acid and 4-methoxysalicylaldehyde were mixed and stirred in methanol for 2 h at ambient temperature. The resulting mixture was concentrated under recuced pressure. The residue, purified by washing with cold methanol and diethyl ether, afforded the pure product of the hydrazone compound. Colorless blocks of (I) were obtained by recrystallization of the product from 95% ethanol.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Ellipsoid plot of the title compound at the 30% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. O–H···N hydrogen bond is drawn by a dashed line.
	Fig. 2. The molecular packing of the title compound, viewed along the c axis. Hydrogen bonds are drawn as dashed lines.

2-[(2-Hydroxy-4-methoxybenzylidene)azaniumyl]benzoate monohydrate top

Crystal data top

C₁₅H₁₃NO₄·H₂O	Z = 2
M_r = 289.28	F(000) = 304
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD diffractometer	2810 independent reflections
Radiation source: fine-focus sealed tube	1992 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→11
T_min = 0.968, T_max = 0.970	k = −11→11
4045 measured reflections	l = −13→13

Refinement top

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(F_o²) + (0.0595P)² + 0.0161P] where P = (F_o² + 2F_c²)/3
2810 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.15 e Å⁻³
5 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₅H₁₃NO₄·H₂O	γ = 117.500 (2)°
M_r = 289.28	V = 669.24 (6) Å³
Triclinic, P1	Z = 2
a = 8.7240 (5) Å	Mo Kα radiation
b = 8.9252 (4) Å	µ = 0.11 mm⁻¹
c = 10.7967 (5) Å	T = 298 K
α = 111.312 (2)°	0.30 × 0.28 × 0.28 mm
β = 93.084 (3)°

Data collection top

Bruker SMART CCD diffractometer	2810 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1992 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.970	R_int = 0.013
4045 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	5 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.15 e Å⁻³
2810 reflections	Δρ_min = −0.18 e Å⁻³
203 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₄·H₂O
M_r	289.28
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.7240 (5), 8.9252 (4), 10.7967 (5)
α, β, γ (°)	111.312 (2), 93.084 (3), 117.500 (2)
V (Å³)	669.24 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.28 × 0.28

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.968, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	4045, 2810, 1992
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.122, 1.08
No. of reflections	2810
No. of parameters	203
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.912 (9)	2.137 (19)	2.7257 (17)	121.4 (17)
N1—H1···O2	0.912 (9)	1.877 (16)	2.6366 (17)	139.3 (19)
O1—H1A···O2ⁱ	0.863 (10)	1.724 (11)	2.5675 (16)	165 (2)
O5—H5A···O3ⁱⁱ	0.851 (9)	2.068 (11)	2.907 (2)	169 (2)
O5—H5B···O3	0.858 (9)	1.948 (9)	2.806 (2)	178 (2)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y, −z+1.

Acknowledgements

The authors acknowledge the Pivot Construction Subject of Applied Chemistry and the Teaching Group of the Courses Construction on Engineering Course Chemistry for financial support.

References

Alpaslan, Y. B., Alpaslan, G., Agar, A. & Isik, S. (2010b). Acta Cryst. E66, o510. Web of Science CSD CrossRef IUCr Journals Google Scholar
Alpaslan, G., Macit, M., Büyükgüngör, O. & Erdönmez, A. (2010a). Acta Cryst. E66, o1178. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aritake, Y., Watanabe, Y. & Akitsu, T. (2010). Acta Cryst. E66, o749. Web of Science CrossRef IUCr Journals Google Scholar
Bahron, H., Bakar, S. N. A., Kassim, K., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o883. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hang, Z.-X. (2010). Acta Cryst. E66, o1650. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar