(S)-2-[(2-Hy­droxy­benz­yl)aza­nium­yl]-4-(methyl­sulfan­yl)butano­ate

Brancatelli, G.; Bruno, G.; Nicoló, F.; Canfora, L.; Ruisi, G.

doi:10.1107/S1600536811016564

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1366-o1367

doi:10.1107/S1600536811016564

Open

access

(S)-2-[(2-Hydroxybenzyl)azaniumyl]-4-(methylsulfanyl)butanoate

Giovanna Brancatelli,^a ^* Giuseppe Bruno,^a Francesco Nicoló,^a Loredana Canfora ^b and Giuseppe Ruisi ^b

^aDip. di Chimica Inorganica Chimica Analitica e Chimica Fisica, Universitá degli Studi di Messina, Via Salita Sperone 31, I-98166 Vill. S. Agata–Messina, Italy, and ^bDip. di Chimica Inorganica e Analitica Stanislao Cannizzaro, Università di Palermo, Viale delle Scienze, I-90128 Palermo, Italy
^*Correspondence e-mail: gbrancatelli@unime.it

(Received 18 February 2011; accepted 2 May 2011; online 11 May 2011)

The zwitterionic title compound, C₁₂H₁₇NO₃S, is a reduced Schiff base derived from (S)-N-(2-hydroxybenzylidene)methionine. An intramolecular interaction between the N—H and carboxylate groups forms a roughly planar (r.m.s. deviation = 0.1405 Å) five-membered ring containing the H(N), N, Cα, C(carboxylate) and O atoms in a pentagonal conformation. In the crystal, a supramolecular triangle-shaped motif is generated by molecules held together by O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For transition metal complexes containing N-(2-hydroxybenzyl)-α-amino acids as ligands, see: Bandyopadhyay et al. (2006 ); Beltrán et al. (2002 ); Ganguly et al. (2008 ); Koh et al. (1996 ); Martell (1989 ); Maurya (2003 ); Nefkens & Zwanenburg (1985 ); Ritsma (1975 ); Shongwe et al. (1999 ); Sreenivasulu & Vittal (2004 ); Wilson (1990 ).

Experimental

Crystal data

C₁₂H₁₇NO₃S
M_r = 255.33
Triclinic, P 1
a = 5.3221 (2) Å
b = 5.8369 (2) Å
c = 10.5564 (5) Å
α = 98.200 (3)°
β = 90.780 (3)°
γ = 96.849 (3)°
V = 322.10 (2) Å³
Z = 1
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.53 × 0.44 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.679, T_max = 0.746
7430 measured reflections
2324 independent reflections
1966 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.179
S = 1.07
2324 reflections
156 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.79 e Å⁻³
Δρ_min = −0.41 e Å⁻³
Absolute structure: Assigned from the known absolute structure of the starting material; the Flack (1983 ) parameter is consistent with this assignment, 1119 Friedel pairs
Flack parameter: 0.12 (19)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.83	2.641 (3)	168
N1—H1A⋯O3ⁱⁱ	0.9	1.83	2.713 (3)	166
N1—H1B⋯O1ⁱⁱⁱ	0.9	2.14	2.916 (4)	144
N1—H1B⋯O2	0.9	2.35	2.687 (3)	102
Symmetry codes: (i) x-1, y+1, z; (ii) x, y+1, z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811016564/fy2002sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016564/fy2002Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016564/fy2002Isup3.cml

checkCIF report

Comment top

Considerable attention has been devoted to both Schiff bases and reduced Schiff bases derived from salicylaldehyde and α-amino acids, since their transition metal complexes are closely analogous to the metal-free systems formed as intermediates in many reactions involving the vitamin B6, such as transamination, decarboxylation, α- and β-elimination and racemization (Martell, 1989). In this regard, copper(II) complexes of N-(2-hydroxybenzyl)-α-amino acids have been studied as models for the intermediate species that occur in the biological reactions mentioned above (Koh et al., 1996) and such reduced Schiff bases have been used as chelating agents for organoboron (Nefkens et al., 1985; Beltrán et al., 2002) and transition metals such as copper (Koh et al., 1996), zinc (Ritsma, 1975), cobalt (Bandyopadhyay et al., 2006), nickel (Sreenivasulu et al., 2004), manganese (Shongwe et al., 1999), technetium (Wilson, 1990) and vanadium (Maurya, 2003). These ligands are more stable than the Schiff bases from which they originate and are suitable to provide conformationally flexible rings in complexation. This results in different solid state architectures, and the presence of hydrogen bond donors and acceptors enables the design and construction of supramolecular, three-dimensional networks (Ganguly et al., 2008). This paper describes the structural characterization of the reduced Schiff base (S)-N-(2-hydroxybenzyl)methionine (I).

Figure 1 shows the molecular structure of (I). The crystal structure analysis clearly indicates that the amino acid is a pure enantiomer, since the compound crystallizes in the chiral P1 space group. In Figure 1 the L-enantiomer is shown with S absolute configuration at C8, in agreement with the synthetic precursor, L-(S)-methionine. The carboxylic acid has been found in the deprotonated —(COO)^- form, with the C9—O2 and C9—O3 bond distances being very similar. Meanwhile, N1 is protonated in the NH₂⁺ form. Therefore compound (I) crystallizes as a zwitterion. The angle N1—C8—C9 is lower in comparison to the angles N1—C8—C10 and C10—C8—C9. This asymmetry in the angles at the C8 is due to the presence of an intramolecular interaction between the N—H and carboxylate groups forming a roughly planar five-membered ring containing H, N, Cα, C and O atoms in a pentagonal (C₅) conformation.

A very interesting feature encountered in the crystal lattice of (I) is related to the formation of supramolecular triangle-shaped motifs [R²₃(8)] involving molecules held together by O—H···O and N—H···O hydrogen bonds (Figure 2, Table 1). Other hydrogen bonding interactions govern the molecular arrangement in parallel strings extending along the (001) crystallographic plane (Figure 3).

Related literature top

For transition metal complexes containing N-(2-hydroxybenzyl)-α-amino acids as ligands, see: Bandyopadhyay et al. (2006); Beltrán et al. (2002); Ganguly et al. (2008); Koh et al. (1996); Martell (1989); Maurya (2003); Nefkens & Zwanenburg (1985); Ritsma (1975); Shongwe et al. (1999); Sreenivasulu & Vittal (2004); Wilson (1990).

Experimental top

The synthesis of the title compound (I) was performed according to the method previously employed for similar Schiff bases (Koh, et al., 1996), starting from L-(S)-metionine. Recrystallization of (I) from a methanol solution produced single crystals suitable for X-ray diffraction.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : ORTEP drawing with numbering of the atoms. Non H-atoms are represented as displacement ellipsoids plotted at the 50% probability level, while H-atoms bound to heteroatoms are shown as small spheres of arbitrary radius. The intramolecular H-bond is represented by a dashed line.
	Fig. 2. : Supramolecular arrangement of (I): a perpendicular view of the triangular-shaped ring [R²₃(8)], involving three molecules interconnected through the H-bonding interactions N1—H1A···O3, N1—H1B···O1 and O1—H1···O2. Dotted lines indicate H-bonding interactions.
	Fig. 3. : Crystal packing of (I): molecular arrangement in parallel strings extending along the (001) crystallographic plane.

(S)-2-[(2-Hydroxybenzyl)azaniumyl]-4-(methylsulfanyl)butanoate top

Crystal data top

C₁₂H₁₇NO₃S	Z = 1
M_r = 255.33	F(000) = 136
Triclinic, P1	D_x = 1.316 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3221 (2) Å	Cell parameters from 4292 reflections
b = 5.8369 (2) Å	θ = 3.6–27.0°
c = 10.5564 (5) Å	µ = 0.25 mm⁻¹
α = 98.200 (3)°	T = 296 K
β = 90.780 (3)°	Prysmatic, yellow
γ = 96.849 (3)°	0.53 × 0.44 × 0.16 mm
V = 322.10 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	1966 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 26°, θ_min = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.679, T_max = 0.746	k = −7→7
7430 measured reflections	l = −13→13
2324 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.179	w = 1/[σ²(F_o²) + (0.1065P)² + 0.1553P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2324 reflections	Δρ_max = 0.79 e Å⁻³
156 parameters	Δρ_min = −0.41 e Å⁻³
3 restraints	Absolute structure: Assigned from the known absolute structure of the starting material; the Flack (1983) parameter is consistent with this assignment, 1119 Friedel-pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.12 (19)

Crystal data top

C₁₂H₁₇NO₃S	γ = 96.849 (3)°
M_r = 255.33	V = 322.10 (2) Å³
Triclinic, P1	Z = 1
a = 5.3221 (2) Å	Mo Kα radiation
b = 5.8369 (2) Å	µ = 0.25 mm⁻¹
c = 10.5564 (5) Å	T = 296 K
α = 98.200 (3)°	0.53 × 0.44 × 0.16 mm
β = 90.780 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2324 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1966 reflections with I > 2σ(I)
T_min = 0.679, T_max = 0.746	R_int = 0.016
7430 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.179	Δρ_max = 0.79 e Å⁻³
S = 1.07	Δρ_min = −0.41 e Å⁻³
2324 reflections	Absolute structure: Assigned from the known absolute structure of the starting material; the Flack (1983) parameter is consistent with this assignment, 1119 Friedel-pairs
156 parameters	Absolute structure parameter: 0.12 (19)
3 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.1397 (7)	0.8261 (5)	0.6478 (4)	0.0378 (8)
C2	0.1286 (8)	1.0229 (6)	0.7378 (4)	0.0480 (10)
H2	0.0037	1.1192	0.7301	0.058*
C3	0.3045 (9)	1.0752 (9)	0.8391 (4)	0.0595 (11)
H3	0.2993	1.2085	0.8984	0.071*
C4	0.4846 (11)	0.9326 (10)	0.8521 (5)	0.0719 (14)
H4	0.6064	0.9719	0.918	0.086*
C5	0.4866 (8)	0.7305 (8)	0.7677 (5)	0.0592 (11)
H5	0.6034	0.6289	0.7807	0.071*
C6	0.3176 (7)	0.6750 (6)	0.6635 (4)	0.0437 (9)
C7	0.3226 (7)	0.4586 (6)	0.5712 (5)	0.0523 (11)
H7A	0.1526	0.4057	0.5364	0.063*
H7B	0.3754	0.3381	0.6164	0.063*
N1	0.4971 (5)	0.4903 (4)	0.4628 (3)	0.0365 (7)
H1A	0.4664	0.6175	0.4288	0.044*
H1B	0.6586	0.5129	0.4927	0.044*
C12	0.982 (2)	0.7692 (13)	0.1065 (9)	0.125 (3)
H12A	0.8321	0.8384	0.0902	0.187*
H12B	1.1162	0.8272	0.0553	0.187*
H12C	1.0313	0.8083	0.1955	0.187*
C8	0.4605 (9)	0.2821 (6)	0.3620 (4)	0.0528 (11)
H8	0.2775	0.234	0.3533	0.063*
C9	0.5770 (7)	0.0784 (5)	0.4082 (4)	0.0396 (8)
O1	−0.0230 (5)	0.7724 (4)	0.5440 (3)	0.0481 (7)
H1	−0.0734	0.8918	0.5264	0.072*
O2	0.7473 (5)	0.1274 (4)	0.4933 (3)	0.0542 (8)
O3	0.4885 (6)	−0.1164 (4)	0.3543 (3)	0.0543 (8)
S1	0.9203 (4)	0.4659 (3)	0.0671 (2)	0.1140 (8)
C10	0.5426 (11)	0.3361 (8)	0.2347 (5)	0.0673 (14)
H10A	0.4849	0.2056	0.1691	0.081*
H10B	0.4698	0.472	0.2149	0.081*
C11	0.8008 (11)	0.3782 (9)	0.2368 (6)	0.0749 (15)
H11A	0.8727	0.24	0.2535	0.09*
H11B	0.8581	0.5041	0.3051	0.09*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0352 (18)	0.0332 (17)	0.047 (2)	0.0050 (13)	0.0058 (17)	0.0120 (14)
C2	0.049 (2)	0.0382 (19)	0.060 (2)	0.0137 (15)	0.015 (2)	0.0095 (17)
C3	0.064 (3)	0.068 (3)	0.045 (2)	0.008 (2)	0.007 (2)	0.0004 (19)
C4	0.070 (3)	0.091 (4)	0.054 (3)	0.013 (3)	0.000 (3)	0.005 (3)
C5	0.047 (2)	0.071 (3)	0.065 (3)	0.013 (2)	0.002 (2)	0.025 (2)
C6	0.0355 (19)	0.0368 (18)	0.063 (2)	0.0053 (14)	0.0139 (19)	0.0199 (16)
C7	0.037 (2)	0.0255 (16)	0.096 (3)	0.0053 (13)	0.014 (2)	0.0138 (19)
N1	0.0462 (16)	0.0128 (11)	0.0509 (17)	0.0053 (10)	−0.0084 (14)	0.0058 (10)
C12	0.183 (9)	0.078 (4)	0.121 (6)	0.010 (5)	0.017 (6)	0.043 (4)
C8	0.079 (3)	0.0190 (15)	0.059 (2)	0.0112 (16)	−0.025 (2)	0.0016 (15)
C9	0.052 (2)	0.0163 (15)	0.0514 (19)	0.0096 (13)	0.0019 (19)	0.0044 (13)
O1	0.0499 (16)	0.0286 (12)	0.0668 (18)	0.0114 (10)	−0.0099 (15)	0.0056 (11)
O2	0.0539 (16)	0.0272 (12)	0.082 (2)	0.0108 (10)	−0.0169 (16)	0.0075 (12)
O3	0.081 (2)	0.0182 (12)	0.0622 (17)	0.0056 (11)	−0.0112 (16)	0.0037 (11)
S1	0.1068 (14)	0.1004 (13)	0.1180 (14)	−0.0026 (10)	0.0483 (12)	−0.0327 (11)
C10	0.092 (4)	0.046 (2)	0.064 (3)	0.011 (2)	−0.016 (3)	0.007 (2)
C11	0.087 (4)	0.057 (3)	0.078 (3)	0.026 (2)	−0.033 (3)	−0.009 (2)

Geometric parameters (Å, º) top

C1—O1	1.365 (5)	N1—H1B	0.9
C1—C2	1.389 (5)	C12—S1	1.749 (8)
C1—C6	1.392 (5)	C12—H12A	0.96
C2—C3	1.387 (7)	C12—H12B	0.96
C2—H2	0.93	C12—H12C	0.96
C3—C4	1.360 (7)	C8—C10	1.483 (7)
C3—H3	0.93	C8—C9	1.539 (4)
C4—C5	1.375 (7)	C8—H8	0.98
C4—H4	0.93	C9—O3	1.232 (4)
C5—C6	1.388 (6)	C9—O2	1.246 (5)
C5—H5	0.93	O1—H1	0.82
C6—C7	1.484 (6)	S1—C11	2.023 (7)
C7—N1	1.502 (5)	C10—C11	1.366 (8)
C7—H7A	0.97	C10—H10A	0.97
C7—H7B	0.97	C10—H10B	0.97
N1—C8	1.489 (4)	C11—H11A	0.97
N1—H1A	0.9	C11—H11B	0.97

O1—C1—C2	121.9 (3)	S1—C12—H12A	109.5
O1—C1—C6	118.1 (3)	S1—C12—H12B	109.5
C2—C1—C6	120.0 (3)	H12A—C12—H12B	109.5
C3—C2—C1	119.7 (4)	S1—C12—H12C	109.5
C3—C2—H2	120.1	H12A—C12—H12C	109.5
C1—C2—H2	120.1	H12B—C12—H12C	109.5
C4—C3—C2	120.3 (4)	C10—C8—N1	112.6 (3)
C4—C3—H3	119.8	C10—C8—C9	115.0 (4)
C2—C3—H3	119.8	N1—C8—C9	109.9 (3)
C3—C4—C5	120.0 (5)	C10—C8—H8	106.2
C3—C4—H4	120	N1—C8—H8	106.2
C5—C4—H4	120	C9—C8—H8	106.2
C4—C5—C6	121.2 (4)	O3—C9—O2	127.9 (3)
C4—C5—H5	119.4	O3—C9—C8	114.6 (3)
C6—C5—H5	119.4	O2—C9—C8	117.5 (3)
C5—C6—C1	118.4 (4)	C1—O1—H1	109.5
C5—C6—C7	121.2 (4)	C12—S1—C11	100.5 (3)
C1—C6—C7	120.4 (4)	C11—C10—C8	108.8 (4)
C6—C7—N1	113.2 (3)	C11—C10—H10A	109.9
C6—C7—H7A	108.9	C8—C10—H10A	109.9
N1—C7—H7A	108.9	C11—C10—H10B	109.9
C6—C7—H7B	108.9	C8—C10—H10B	109.9
N1—C7—H7B	108.9	H10A—C10—H10B	108.3
H7A—C7—H7B	107.8	C10—C11—S1	110.1 (4)
C8—N1—C7	110.7 (3)	C10—C11—H11A	109.6
C8—N1—H1A	109.5	S1—C11—H11A	109.6
C7—N1—H1A	109.5	C10—C11—H11B	109.6
C8—N1—H1B	109.5	S1—C11—H11B	109.6
C7—N1—H1B	109.5	H11A—C11—H11B	108.1
H1A—N1—H1B	108.1

O1—C1—C2—C3	−177.5 (4)	C1—C6—C7—N1	91.8 (4)
C6—C1—C2—C3	3.7 (6)	C6—C7—N1—C8	−169.9 (3)
C1—C2—C3—C4	−1.2 (7)	C7—N1—C8—C10	156.6 (4)
C2—C3—C4—C5	−2.7 (8)	C7—N1—C8—C9	−73.8 (4)
C3—C4—C5—C6	4.3 (8)	C10—C8—C9—O3	−74.6 (5)
C4—C5—C6—C1	−1.8 (6)	N1—C8—C9—O3	157.1 (3)
C4—C5—C6—C7	179.0 (5)	C10—C8—C9—O2	105.0 (4)
O1—C1—C6—C5	178.9 (4)	N1—C8—C9—O2	−23.4 (5)
C2—C1—C6—C5	−2.2 (5)	N1—C8—C10—C11	71.0 (5)
O1—C1—C6—C7	−1.8 (5)	C9—C8—C10—C11	−55.9 (5)
C2—C1—C6—C7	177.1 (4)	C8—C10—C11—S1	−177.7 (3)
C5—C6—C7—N1	−89.0 (5)	C12—S1—C11—C10	100.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.83	2.641 (3)	168
N1—H1A···O3ⁱⁱ	0.9	1.83	2.713 (3)	166
N1—H1B···O1ⁱⁱⁱ	0.9	2.14	2.916 (4)	144
N1—H1B···O2	0.9	2.35	2.687 (3)	102

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇NO₃S
M_r	255.33
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.3221 (2), 5.8369 (2), 10.5564 (5)
α, β, γ (°)	98.200 (3), 90.780 (3), 96.849 (3)
V (Å³)	322.10 (2)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.53 × 0.44 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.679, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	7430, 2324, 1966
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.179, 1.07
No. of reflections	2324
No. of parameters	156
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.79, −0.41
Absolute structure	Assigned from the known absolute structure of the starting material; the Flack (1983) parameter is consistent with this assignment, 1119 Friedel-pairs
Absolute structure parameter	0.12 (19)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.83	2.641 (3)	168
N1—H1A···O3ⁱⁱ	0.9	1.83	2.713 (3)	166
N1—H1B···O1ⁱⁱⁱ	0.9	2.14	2.916 (4)	144
N1—H1B···O2	0.9	2.35	2.687 (3)	102

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

Acknowledgements

The authors thank the University of Messina and the MIUR (Ministero dell'Istruzione, dell'Universitá e della Ricerca) for financial support.

References

Bandyopadhyay, S., Mukherjee, G. N. & Drew, M. G. B. (2006). Inorg. Chim. Acta, 359, 3243–3251. CrossRef CAS Google Scholar
Beltrán, H. I., Zamudio-Rivera, L. S., Mancilla, T., Santillan, R. & Farfán, N. (2002). J. Organomet. Chem. 657, 194–204. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ganguly, R., Sreenivasulu, B. & Vittal, J. J. (2008). Coord. Chem. Rev. 252, 1027–1050. Web of Science CrossRef CAS Google Scholar
Koh, L. L., Ranford, J. O., Robinson, W. T., Svensson, J. O., Tan, A. L. C. & Wu, D. (1996). Inorg. Chem. 35, 6466–6472. CSD CrossRef PubMed CAS Web of Science Google Scholar
Martell, A. E. (1989). Acc. Chem. Res. 22, 115–124. CrossRef CAS Google Scholar
Maurya, M. R. (2003). Coord. Chem. Rev. 237, 163–181. CrossRef CAS Google Scholar
Nefkens, G. H. L. & Zwanenburg, B. (1985). Tetrahedron, 41, 6063–6066. CrossRef CAS Google Scholar
Ritsma, J. H. (1975). Rec. Trav. Chim. Pays-Bas, 94, 174–178. CrossRef CAS 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
Shongwe, M. S., Mikuriya, M., Nukada, R., Ainscough, E. W., Brodie, A. M. & Waters, J. M. (1999). Inorg. Chim. Acta, 290, 228–236. CrossRef CAS Google Scholar
Sreenivasulu, B. & Vittal, J. J. (2004). Angew. Chem. Int. Ed. 43, 5769–5772. Web of Science CSD CrossRef CAS Google Scholar
Wilson, J. G. (1990). Aust. J. Chem. 43, 1283–1289. CrossRef CAS Google Scholar