4-[(2,4-Dihydroxy­benzyl­idene)ammonio]benzene­sulfonate trihydrate

Yeap, C.S.; Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536810004526

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Pages o580-o581

doi:10.1107/S1600536810004526

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4-[(2,4-Dihydroxybenzylidene)ammonio]benzenesulfonate trihydrate

Chin Sing Yeap,^a ‡ Madhukar Hemamalini ^a and Hoong-Kun Fun ^a ^*§

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 27 January 2010; accepted 4 February 2010; online 10 February 2010)

The title Schiff base compound, C₁₃H₁₁NO₅S·3H₂O, formed from sulfanilic acid and 2,4-dihydroxybenzaldehyde, crystallized out as a zwitterion with the N atom protonated. The asymmetric unit consists of one 4-[(2,4-dihydroxybenzylidene)ammonio]benzenesulfonate and three water molecules. The zwitterion exists in an E configuration with respect to the central C=N double bond. The two benzene rings of the molecule are oriented at a dihedral angle of 27.33 (8)°. An intramolecular N–H⋯O hydrogen bond stabilizes the molecular structure. In the crystal, the zwitterions are linked into chains along [101] by intermolecular O—H⋯O and N—H⋯O hydrogen bonds. The three water molecules link these chains into a three-dimensional framework by additional intermolecular O—H⋯O hydrogen bonds. A π⋯π interaction [3.5485 (9) Å] further stabilizes the crystal structure.

Related literature

For Schiff bases and their applications, see: Singh et al. (1975 ); Elmali et al. (1999 ); Patel et al. (1999 ). For details of sulfanilic acid, see: Rae & Maslen (1962 ); Banu & Golzar Hossain (2006 ); Hempel et al. (1999 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₁NO₅S·3H₂O
M_r = 347.34
Triclinic, $[P \overline 1]$
a = 7.7855 (1) Å
b = 9.0820 (1) Å
c = 11.8526 (2) Å
α = 70.022 (1)°
β = 79.271 (1)°
γ = 76.141 (1)°
V = 759.70 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.36 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.914, T_max = 0.980
19799 measured reflections
5420 independent reflections
4177 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.147
S = 1.05
5420 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3ⁱ	0.89	2.17	3.020 (3)	161
O1W—H1W1⋯O4ⁱ	0.89	2.39	3.083 (3)	135
O1W—H2W1⋯O2W	0.84	2.02	2.817 (4)	158
O2W—H2W2⋯O2	0.95	1.89	2.812 (3)	161
O3W—H1W3⋯O5ⁱⁱ	0.96	1.83	2.756 (2)	161
O3W—H2W3⋯O1W	0.86	1.86	2.701 (3)	166
N1—H1N1⋯O1	0.86 (3)	2.07 (2)	2.6601 (18)	126 (2)
N1—H1N1⋯O5ⁱⁱⁱ	0.86 (3)	2.19 (3)	2.948 (2)	148 (2)
O1—H1O1⋯O3W	0.90 (3)	1.64 (4)	2.543 (2)	173 (4)
O2—H1O2⋯O3^iv	0.80 (3)	1.85 (3)	2.627 (2)	164 (2)
Symmetry codes: (i) x-1, y, z-1; (ii) x, y, z-1; (iii) -x+1, -y+1, -z+2; (iv) x-1, y+1, z-1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810004526/sj2719sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004526/sj2719Isup2.hkl

checkCIF report

Comment top

Schiff bases derived from aromatic amines and aromatic aldehydes have a wide variety of applications in many fields, e.g., biological, inorganic and analytical chemistry (Singh et al., 1975; Elmali et al., 1999; Patel et al., 1999). Schiff base compounds have been of great interest for many years. p-aminobenzenesulfonic acid is known as sulfanilic acid, which contains NH₃⁺ and SO₃^- groups. Sulfanilic acid is a salt, but of a rather special kind, called a zwitterion. It is the product of the reaction between an acidic group and a basic group that are part of the same molecule. The hydrogen is attached to nitrogen rather than oxygen simply because the NH₂ group is a stronger base than the SO₃^- substituent. A zwitterionic structure was also observed in the crystal structure of sulfanilic acid monohydrate (Rae & Maslen, 1962; Banu & Golzar, 2006). The crystal structure of the Schiff base formed from sulfanilic acid and dimethylformamide has also been reported in the literature (Hempel et al., 1999). The present work is part of a structural study of compounds of Schiff base systems and we report here the structure of the title compound, (I).

The 4-[(2,4-dihydroxybenzylidene)-amino]benzenesulfonic acid molecule crystallized out as a zwitterion, 4-[(2,4-dihydroxybenzylidene)-ammonio]benzenesulfonate. The asymmetric unit consists of one 4-[(2,4-dihydroxybenzylidene)-ammonio]benzenesulfonate and three water molecules (Fig. 1). The zwitterion exists in an E configuration with respect to the central C=N double bond. The two benzene rings [C1–C6 and C8–C13] are oriented at 27.33 (8)°. An intramolecular N1–H1N1···O1 hydrogen bond forms a six-membered ring, generating S(6) ring motif (Bernstein et al., 1995). The zwitterions are linked into chains along [101] by intermolecular O2–H1O2···O3 and N1–H1N1···O5 hydrogen bonds. The three water molecules linked these chains into a three-dimensional framework by intermolecular O–H···O hydrogen bonds (Fig. 2, Table 2). An unusually short H2W1···H1W2 distance is also observed. A Cg1···Cg1 interaction of 3.5485 (9) Å; -x, 2-y, 1-z, further stabilizes the crystal structure [Cg1 is the centroid of the C1–C6 benzene ring].

Related literature top

For Schiff bases and their applications, see: Singh et al. (1975); Elmali et al. (1999); Patel et al. (1999). For details of sulfanilic acid, see: Rae & Maslen (1962); Banu & Golzar (2006); Hempel et al. (1999). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

2,4-Dihydroxybenzaldehyde (0.069 g) and sulfanilic acid (0.861 g) in ethanol/water (40 ml) were heated under reflux for 2 h with stirring. The colour of the solution gradually changed from colourless to lemon yellow. The solution was then cooled to room temperature. After few days, slow evaporation of the solvent yielded yellow crystals of compound (I).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with atom labels and 50% probability ellipsoids for non-H atoms. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. The crystal packing of (I), viewed down the b axis, showing the molecules linked into a 3-dimensional framework. Intermolecular hydrogen bonds are shown as dashed lines.

4-[(2,4-Dihydroxybenzylidene)ammonio]benzenesulfonate trihydrate top

Crystal data top

C₁₃H₁₁NO₅S·3H₂O	Z = 2
M_r = 347.34	F(000) = 364
Triclinic, P1	D_x = 1.518 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7855 (1) Å	Cell parameters from 7701 reflections
b = 9.0820 (1) Å	θ = 2.6–32.1°
c = 11.8526 (2) Å	µ = 0.26 mm⁻¹
α = 70.022 (1)°	T = 100 K
β = 79.271 (1)°	Block, yellow
γ = 76.141 (1)°	0.36 × 0.16 × 0.08 mm
V = 759.70 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5420 independent reflections
Radiation source: fine-focus sealed tube	4177 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 32.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.914, T_max = 0.980	k = −13→13
19799 measured reflections	l = −17→17

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.070P)² + 0.4045P] where P = (F_o² + 2F_c²)/3
5420 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₁₃H₁₁NO₅S·3H₂O	γ = 76.141 (1)°
M_r = 347.34	V = 759.70 (2) Å³
Triclinic, P1	Z = 2
a = 7.7855 (1) Å	Mo Kα radiation
b = 9.0820 (1) Å	µ = 0.26 mm⁻¹
c = 11.8526 (2) Å	T = 100 K
α = 70.022 (1)°	0.36 × 0.16 × 0.08 mm
β = 79.271 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5420 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4177 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.980	R_int = 0.027
19799 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.61 e Å⁻³
5420 reflections	Δρ_min = −0.60 e Å⁻³
220 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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

	x	y	z	U_iso*/U_eq
S1	0.71640 (6)	0.60676 (5)	1.18660 (4)	0.02504 (12)
O1	0.33982 (17)	0.77778 (14)	0.52286 (11)	0.0226 (2)
O2	0.00861 (17)	1.21132 (17)	0.24684 (11)	0.0256 (3)
O3	0.89905 (19)	0.52191 (18)	1.16735 (13)	0.0371 (3)
O4	0.7119 (3)	0.75067 (16)	1.21434 (16)	0.0530 (5)
O5	0.60457 (18)	0.50241 (15)	1.27306 (10)	0.0267 (3)
N1	0.41704 (17)	0.82152 (16)	0.71713 (11)	0.0170 (2)
C1	0.2641 (2)	0.93133 (18)	0.48282 (13)	0.0170 (3)
C2	0.1775 (2)	0.99664 (19)	0.37933 (13)	0.0190 (3)
H2A	0.1728	0.9331	0.3333	0.023*
C3	0.0980 (2)	1.15723 (19)	0.34488 (13)	0.0195 (3)
C4	0.1103 (2)	1.25788 (19)	0.40959 (14)	0.0207 (3)
H4A	0.0593	1.3658	0.3843	0.025*
C5	0.1987 (2)	1.19458 (18)	0.51051 (14)	0.0188 (3)
H5A	0.2090	1.2609	0.5528	0.023*
C6	0.2748 (2)	1.02971 (17)	0.55143 (13)	0.0162 (3)
C7	0.3521 (2)	0.97063 (18)	0.66134 (13)	0.0171 (3)
H7A	0.3572	1.0454	0.6975	0.021*
C8	0.4854 (2)	0.76888 (17)	0.83072 (13)	0.0169 (3)
C9	0.4177 (2)	0.85045 (19)	0.91434 (14)	0.0212 (3)
H9A	0.3246	0.9379	0.8979	0.025*
C10	0.4905 (2)	0.79988 (19)	1.02271 (14)	0.0219 (3)
H10A	0.4466	0.8537	1.0793	0.026*
C11	0.6291 (2)	0.66864 (18)	1.04650 (14)	0.0197 (3)
C12	0.6933 (2)	0.58417 (18)	0.96441 (14)	0.0203 (3)
H12A	0.7847	0.4954	0.9817	0.024*
C13	0.6196 (2)	0.63345 (18)	0.85627 (14)	0.0188 (3)
H13A	0.6595	0.5765	0.8014	0.023*
O1W	0.1128 (3)	0.7226 (3)	0.22066 (18)	0.0639 (6)
H1W1	0.0299	0.6832	0.2044	0.096*
H2W1	0.0754	0.8189	0.1836	0.096*
O2W	0.0858 (3)	1.0446 (3)	0.0769 (2)	0.0815 (7)
H1W2	0.1929	0.9994	0.0628	0.122*
H2W2	0.0424	1.1170	0.1224	0.122*
O3W	0.3001 (2)	0.59375 (18)	0.41308 (14)	0.0368 (3)
H1W3	0.4180	0.5558	0.3796	0.055*
H2W3	0.2254	0.6348	0.3604	0.055*
H1N1	0.415 (3)	0.747 (3)	0.689 (2)	0.041 (7)*
H1O1	0.327 (4)	0.719 (4)	0.478 (3)	0.057 (8)*
H1O2	−0.027 (3)	1.305 (3)	0.236 (2)	0.036 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0369 (2)	0.01588 (18)	0.0241 (2)	−0.00608 (15)	−0.01801 (17)	−0.00021 (14)
O1	0.0310 (6)	0.0164 (5)	0.0212 (5)	−0.0008 (4)	−0.0084 (5)	−0.0063 (4)
O2	0.0257 (6)	0.0297 (7)	0.0188 (5)	−0.0058 (5)	−0.0101 (5)	−0.0001 (5)
O3	0.0291 (7)	0.0386 (8)	0.0338 (7)	−0.0045 (6)	−0.0170 (6)	0.0066 (6)
O4	0.0943 (14)	0.0183 (6)	0.0590 (10)	−0.0066 (7)	−0.0542 (10)	−0.0072 (6)
O5	0.0367 (7)	0.0239 (6)	0.0173 (5)	−0.0029 (5)	−0.0064 (5)	−0.0037 (4)
N1	0.0192 (6)	0.0167 (6)	0.0146 (5)	−0.0028 (5)	−0.0048 (4)	−0.0031 (5)
C1	0.0172 (6)	0.0175 (6)	0.0165 (6)	−0.0047 (5)	−0.0019 (5)	−0.0047 (5)
C2	0.0198 (7)	0.0228 (7)	0.0158 (6)	−0.0070 (5)	−0.0033 (5)	−0.0051 (5)
C3	0.0176 (7)	0.0241 (7)	0.0145 (6)	−0.0066 (5)	−0.0037 (5)	−0.0004 (5)
C4	0.0208 (7)	0.0186 (7)	0.0195 (7)	−0.0035 (5)	−0.0043 (6)	−0.0008 (5)
C5	0.0219 (7)	0.0161 (6)	0.0175 (6)	−0.0034 (5)	−0.0042 (5)	−0.0033 (5)
C6	0.0177 (6)	0.0159 (6)	0.0145 (6)	−0.0032 (5)	−0.0035 (5)	−0.0031 (5)
C7	0.0193 (7)	0.0165 (6)	0.0152 (6)	−0.0035 (5)	−0.0047 (5)	−0.0031 (5)
C8	0.0174 (6)	0.0165 (6)	0.0150 (6)	−0.0039 (5)	−0.0044 (5)	−0.0012 (5)
C9	0.0247 (7)	0.0184 (7)	0.0182 (7)	0.0005 (6)	−0.0065 (6)	−0.0039 (5)
C10	0.0288 (8)	0.0176 (7)	0.0183 (7)	−0.0018 (6)	−0.0067 (6)	−0.0038 (5)
C11	0.0234 (7)	0.0158 (6)	0.0194 (7)	−0.0068 (5)	−0.0082 (6)	0.0004 (5)
C12	0.0192 (7)	0.0170 (7)	0.0211 (7)	−0.0025 (5)	−0.0063 (5)	−0.0002 (5)
C13	0.0195 (7)	0.0176 (6)	0.0178 (6)	−0.0031 (5)	−0.0025 (5)	−0.0038 (5)
O1W	0.0496 (11)	0.1022 (17)	0.0610 (12)	−0.0363 (11)	−0.0095 (9)	−0.0358 (12)
O2W	0.0746 (15)	0.120 (2)	0.0831 (16)	−0.0358 (15)	0.0051 (12)	−0.0697 (16)
O3W	0.0402 (8)	0.0364 (7)	0.0420 (8)	−0.0097 (6)	0.0007 (6)	−0.0238 (6)

Geometric parameters (Å, º) top

S1—O4	1.4441 (14)	C5—H5A	0.9300
S1—O5	1.4512 (14)	C6—C7	1.417 (2)
S1—O3	1.4636 (15)	C7—H7A	0.9300
S1—C11	1.7706 (16)	C8—C9	1.389 (2)
O1—C1	1.3325 (18)	C8—C13	1.394 (2)
O1—H1O1	0.90 (3)	C9—C10	1.388 (2)
O2—C3	1.3500 (18)	C9—H9A	0.9300
O2—H1O2	0.80 (3)	C10—C11	1.390 (2)
N1—C7	1.3083 (19)	C10—H10A	0.9300
N1—C8	1.4247 (19)	C11—C12	1.389 (2)
N1—H1N1	0.85 (3)	C12—C13	1.390 (2)
C1—C2	1.389 (2)	C12—H12A	0.9300
C1—C6	1.422 (2)	C13—H13A	0.9300
C2—C3	1.390 (2)	O1W—H1W1	0.8863
C2—H2A	0.9300	O1W—H2W1	0.8403
C3—C4	1.408 (2)	O2W—H1W2	0.8500
C4—C5	1.372 (2)	O2W—H2W2	0.9519
C4—H4A	0.9300	O3W—H1W3	0.9617
C5—C6	1.419 (2)	O3W—H2W3	0.8594

O4—S1—O5	113.78 (10)	C7—C6—C1	123.35 (13)
O4—S1—O3	111.65 (11)	C5—C6—C1	118.67 (13)
O5—S1—O3	111.87 (8)	N1—C7—C6	126.60 (14)
O4—S1—C11	106.23 (8)	N1—C7—H7A	116.7
O5—S1—C11	106.54 (8)	C6—C7—H7A	116.7
O3—S1—C11	106.16 (8)	C9—C8—C13	121.03 (14)
C1—O1—H1O1	114.3 (19)	C9—C8—N1	120.33 (13)
C3—O2—H1O2	106.3 (18)	C13—C8—N1	118.64 (13)
C7—N1—C8	123.83 (13)	C10—C9—C8	119.21 (14)
C7—N1—H1N1	121.2 (17)	C10—C9—H9A	120.4
C8—N1—H1N1	114.9 (17)	C8—C9—H9A	120.4
O1—C1—C2	123.11 (14)	C9—C10—C11	119.89 (15)
O1—C1—C6	116.94 (13)	C9—C10—H10A	120.1
C2—C1—C6	119.94 (14)	C11—C10—H10A	120.1
C1—C2—C3	119.77 (14)	C12—C11—C10	120.89 (14)
C1—C2—H2A	120.1	C12—C11—S1	120.66 (12)
C3—C2—H2A	120.1	C10—C11—S1	118.41 (12)
O2—C3—C2	116.77 (15)	C11—C12—C13	119.41 (14)
O2—C3—C4	121.90 (15)	C11—C12—H12A	120.3
C2—C3—C4	121.33 (14)	C13—C12—H12A	120.3
C5—C4—C3	119.07 (14)	C12—C13—C8	119.48 (14)
C5—C4—H4A	120.5	C12—C13—H13A	120.3
C3—C4—H4A	120.5	C8—C13—H13A	120.3
C4—C5—C6	121.14 (14)	H1W1—O1W—H2W1	97.0
C4—C5—H5A	119.4	H1W2—O2W—H2W2	127.8
C6—C5—H5A	119.4	H1W3—O3W—H2W3	113.2
C7—C6—C5	117.94 (13)

O1—C1—C2—C3	178.43 (14)	C7—N1—C8—C13	−150.63 (15)
C6—C1—C2—C3	−1.5 (2)	C13—C8—C9—C10	2.8 (2)
C1—C2—C3—O2	−176.86 (14)	N1—C8—C9—C10	−177.92 (15)
C1—C2—C3—C4	3.1 (2)	C8—C9—C10—C11	−0.2 (2)
O2—C3—C4—C5	178.14 (14)	C9—C10—C11—C12	−1.7 (3)
C2—C3—C4—C5	−1.8 (2)	C9—C10—C11—S1	−179.29 (13)
C3—C4—C5—C6	−1.1 (2)	O4—S1—C11—C12	146.08 (15)
C4—C5—C6—C7	−175.27 (15)	O5—S1—C11—C12	−92.28 (15)
C4—C5—C6—C1	2.5 (2)	O3—S1—C11—C12	27.10 (16)
O1—C1—C6—C7	−3.5 (2)	O4—S1—C11—C10	−36.33 (17)
C2—C1—C6—C7	176.45 (14)	O5—S1—C11—C10	85.31 (14)
O1—C1—C6—C5	178.82 (14)	O3—S1—C11—C10	−155.30 (14)
C2—C1—C6—C5	−1.2 (2)	C10—C11—C12—C13	1.1 (2)
C8—N1—C7—C6	−176.86 (14)	S1—C11—C12—C13	178.61 (12)
C5—C6—C7—N1	174.98 (15)	C11—C12—C13—C8	1.5 (2)
C1—C6—C7—N1	−2.7 (3)	C9—C8—C13—C12	−3.4 (2)
C7—N1—C8—C9	30.1 (2)	N1—C8—C13—C12	177.29 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3ⁱ	0.89	2.17	3.020 (3)	161
O1W—H1W1···O4ⁱ	0.89	2.39	3.083 (3)	135
O1W—H2W1···O2W	0.84	2.02	2.817 (4)	158
O2W—H2W2···O2	0.95	1.89	2.812 (3)	161
O3W—H1W3···O5ⁱⁱ	0.96	1.83	2.756 (2)	161
O3W—H2W3···O1W	0.86	1.86	2.701 (3)	166
N1—H1N1···O1	0.86 (3)	2.07 (2)	2.6601 (18)	126 (2)
N1—H1N1···O5ⁱⁱⁱ	0.86 (3)	2.19 (3)	2.948 (2)	148 (2)
O1—H1O1···O3W	0.90 (3)	1.64 (4)	2.543 (2)	173 (4)
O2—H1O2···O3^iv	0.80 (3)	1.85 (3)	2.627 (2)	164 (2)

Symmetry codes: (i) x−1, y, z−1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+2; (iv) x−1, y+1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₁NO₅S·3H₂O
M_r	347.34
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.7855 (1), 9.0820 (1), 11.8526 (2)
α, β, γ (°)	70.022 (1), 79.271 (1), 76.141 (1)
V (Å³)	759.70 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.36 × 0.16 × 0.08

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.914, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	19799, 5420, 4177
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.754

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.147, 1.05
No. of reflections	5420
No. of parameters	220
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.60

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3ⁱ	0.8900	2.1700	3.020 (3)	161.00
O1W—H1W1···O4ⁱ	0.8900	2.3900	3.083 (3)	135.00
O1W—H2W1···O2W	0.8400	2.0200	2.817 (4)	158.00
O2W—H2W2···O2	0.9500	1.8900	2.812 (3)	161.00
O3W—H1W3···O5ⁱⁱ	0.9600	1.8300	2.756 (2)	161.00
O3W—H2W3···O1W	0.8600	1.8600	2.701 (3)	166.00
N1—H1N1···O1	0.86 (3)	2.07 (2)	2.6601 (18)	126 (2)
N1—H1N1···O5ⁱⁱⁱ	0.86 (3)	2.19 (3)	2.948 (2)	148 (2)
O1—H1O1···O3W	0.90 (3)	1.64 (4)	2.543 (2)	173 (4)
O2—H1O2···O3^iv	0.80 (3)	1.85 (3)	2.627 (2)	164 (2)

Symmetry codes: (i) x−1, y, z−1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z+2; (iv) x−1, y+1, z−1.

Footnotes

‡Thomson Reuters ResearcherID: A-5523-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

MH and HKF thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH thanks USM for a post-doctoral research fellowship and CSY thanks USM for the award of a USM Fellowship.

References

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