(S)-2-[(2-Hy-droxy-benz-yl)aza-nium-yl]-4-(methyl-sulfan-yl)butano-ate.

The zwitterionic title compound, C(12)H(17)NO(3)S, is a reduced Schiff base derived from (S)-N-(2-hy-droxy-benzyl-idene)methio-nine. An intra-molecular inter-action between the N-H and carboxyl-ate groups forms a roughly planar (r.m.s. deviation = 0.1405 Å) five-membered ring containing the H(N), N, Cα, C(carboxyl-ate) and O atoms in a penta-gonal conformation. In the crystal, a supra-molecular triangle-shaped motif is generated by mol-ecules 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 = 255.33

Triclinic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.179

S = 1.07

2324 reflections

156 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −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)

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.

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

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

Supplementary material file. DOI: 10.1107/S1600536811016564/fy2002Isup3.cml

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

C12H17NO3S	Z = 1
Mr = 255.33	F(000) = 136
Triclinic, P1	Dx = 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

Bruker APEXII CCD diffractometer	1966 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 26°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.679, Tmax = 0.746	k = −7→7
7430 measured reflections	l = −13→13
2324 independent reflections

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(Fo2) + (0.1065P)2 + 0.1553P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2324 reflections	Δρmax = 0.79 e Å−3
156 parameters	Δρmin = −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	Flack parameter: 0.12 (19)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .