tert-Butyl 2-hy­droxy-3-(4-methyl­benzene­sulfonamido)­butano­ate

Fadlalla, M.I.; Friedrich, H.B.; Maguire, G.E.M.; Omondi, B.

doi:10.1107/S1600536811004934

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o648

doi:10.1107/S1600536811004934

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tert-Butyl 2-hydroxy-3-(4-methylbenzenesulfonamido)butanoate

Mohamed I. Fadlalla,^a Holger B. Friedrich,^a Glenn E. M. Maguire ^a and Bernard Omondi ^b ^*

^aSchool of Chemistry, University of KwaZulu–Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa, and ^bResearch Centre for Synthesis and Catalysis, Department of Chemistry, University of Johannesburg, PO Box 524 Auckland Park, Johannesburg 2006, South Africa
^*Correspondence e-mail: boowaga@uj.ac.za

(Received 3 February 2011; accepted 9 February 2011; online 19 February 2011)

In the crystal of the title compound, C₁₅H₂₃NO₅S, molecules are linked through N—H⋯O and O—H⋯O hydrogen-bond interactions, resulting in centrosymmetric dimers in which the N—H⋯O interactions generate R₂²(12) rings and the O—H⋯O interactions generate R₂²(14) rings. Weak intermolecular C—H⋯O interactions are also observed.

Related literature

For related structures of β-amino alcohols, see: Lohray et al. (2002 ); Bodkin et al. (2008 ). For the structures of tosylamino compounds, see: Coote et al. (2008 ); Liu et al. (2005 ); Fadlalla et al. (2010 ). For the synthesis of the title compound, see: Naicker et al. (2008 ); Govender et al. (2003 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₂₃NO₅S
M_r = 329.4
Triclinic, $[P \overline 1]$
a = 9.6038 (8) Å
b = 9.9059 (8) Å
c = 10.1064 (11) Å
α = 119.342 (2)°
β = 92.307 (2)°
γ = 93.422 (2)°
V = 833.95 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.22 × 0.18 × 0.14 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.954, T_max = 0.970
24635 measured reflections
4192 independent reflections
3712 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.083
S = 1.05
4192 reflections
209 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O2ⁱ	0.842 (16)	2.059 (16)	2.8625 (12)	159.5 (14)
O3—H3⋯O4ⁱ	0.84	2.40	3.2041 (12)	162
C1—H1C⋯O4ⁱⁱ	0.98	2.54	3.4936 (14)	164
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004934/hg2795sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004934/hg2795Isup2.hkl

checkCIF report

Comment top

The aminohydroxylation reaction of alkenes is the most simple, single step reaction in the production of β-amino alcohols. The product (β-amino alcohol) is present in many natural products and biologically active compounds (such as Acranil which is an antiprotozoal drug) (Bodkin et al., 2008, Lohray et al., 2002). Furthermore, β-amino alcohols are utilized in asymmetric catalysis in the synthesis of chiral ligands. As part of investigating new heterogeneous route to the aminohydroxylation reaction to produce β-amino alcohols, we report the crystal structure of the title compound (I). The molecular structure of (I) is related to that of (2,3)-Methyl 2-hydroxy-3-(4-methylbenzenesulfonamido)-3-phenylpropanoate (Fadlalla et al., (2010). Other related structures have been reported by Coote et al. (2008) and Liu et al., (2005).

Fig. I shows the asymetric unit of (I). The compound is chiral and has an S chirality at C6 and an R chirality at C7. In the crystal, adjacent molecules are connected by a pair of N—H···O and O—H···O hydrogen bonds (Fig. 2) that result in centrosymmetric dimers that can be described by R₂²(12) and R₂²(14) graph set notations (Bernstein et al. 1995) respectively. In addition, weak C—H···O intermolecular interactions (Table 1) contribute to the stability of the crystal lattice.

Related literature top

For related structures of β-amino alcohols, see: Lohray et al. (2002); Bodkin et al. (2008). For related structures of tosylamino compounds, see: Coote et al. (2008); Liu et al. (2005); Fadlalla et al. (2010). For the synthesis of the title compound, see: Naicker et al. (2008); Govender et al. (2003). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound (I) was obtained through a modified literature method (Naicker et al., 2008, Govender et al., 2003).To a nitrogen saturated Schlenk tube 6 ml of a mixture of acetonitrile and water (1:1 v/v), tert-butylcrotonate (76 µL, 0.478 mmol), chloramine-T (0.956 g, 0.956 mmol), hydrotalcite-like catalyst (0.03 g) were added in that order. The catalyst was gravity filtered off after 15 h. The reaction mixture was then washed with sodium sulfite (1 g in 20 ml of de-ionized water) followed by 15 ml of ethyl acetate. The aqueous layer was separated from the organic layer and further washed by 3x 15 ml of ethyl acetate. The solvent of the combined organic mixture was removed in vacuo. The resulting crude product was purified by preparative high preasure liquid chromatography to yield the title compound as a white solid. Crystals of I were obtained by slow evaporation of a hexane layered solution of the compound in dichloro methane at room temperature (m.p. 142–145 K).

Spectroscopic data: ¹H NMR (400 MHz, CDCl₃, δ. p.p.m.): = 0.9 (d, 3H), 1.5 (s, 9H), 2.4 (s, 3H), 3.2 (d, 1H), 3.8 (m, 2H), 4.7 (d, 1H), 7.3 (d, 2H), 7.7 (d, 2H). ¹³C NMR (100 MHz, CDCl₃, δ. p.p.m.): = 17.9 (s,1 C), 21.5 (s, 1 C), 27.9 (s, 3 C), 51.5 (s, 1 C), 73.6 (s, 1 C), 84.1 (s, 1 C), 126.9 (s, 2 C), 138.6 (s, 1 C), 143.3 (s, 1 C), 171.6 (s, 1 C). IR (cm^-1): = 3446 (m), (OH), 3260 (m), (NH), 2985 (w), 2919 (w), 1598 (w), (ar), 1716 (m), (C=O), 1048 (m), (S=O). Mass calculated = 329, MS = 351 m/z (M + Na).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus and XPREP (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I) (50% probability displacement ellipsoids). H atoms have been omited for clarity.
	Fig. 2. N—H···O and O—H···O hydrogen bond interactions in the crystal structure of (I). [Symmetry operators: (i) = 1 - x, 1 - y, 1 - z; (ii) = 1 - x, 2 - y, 2 - z]

tert-Butyl 2-hydroxy-3-(4-methylbenzenesulfonamido)butanoate top

Crystal data top

C₁₅H₂₃NO₅S	Z = 2
M_r = 329.4	F(000) = 352
Triclinic, P1	D_x = 1.312 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6038 (8) Å	Cell parameters from 24635 reflections
b = 9.9059 (8) Å	θ = 2.1–28.5°
c = 10.1064 (11) Å	µ = 0.22 mm⁻¹
α = 119.342 (2)°	T = 100 K
β = 92.307 (2)°	Block, colourless
γ = 93.422 (2)°	0.22 × 0.18 × 0.14 mm
V = 833.95 (13) Å³

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	3712 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
T_min = 0.954, T_max = 0.970	k = −13→13
24635 measured reflections	l = −13→13
4192 independent reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0395P)² + 0.3237P] where P = (F_o² + 2F_c²)/3
4192 reflections	(Δ/σ)_max = 0.005
209 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₅H₂₃NO₅S	γ = 93.422 (2)°
M_r = 329.4	V = 833.95 (13) Å³
Triclinic, P1	Z = 2
a = 9.6038 (8) Å	Mo Kα radiation
b = 9.9059 (8) Å	µ = 0.22 mm⁻¹
c = 10.1064 (11) Å	T = 100 K
α = 119.342 (2)°	0.22 × 0.18 × 0.14 mm
β = 92.307 (2)°

Data collection top

Bruker X8 APEXII 4K Kappa CCD diffractometer	4192 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3712 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.970	R_int = 0.031
24635 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.45 e Å⁻³
4192 reflections	Δρ_min = −0.39 e Å⁻³
209 parameters

Special details top

Experimental. The intensity data was collected on a Bruker X8 Apex 4 K CCD diffractometer using an exposure time of 15 sec/per frame. A total of 3328 frames were collected with a frame width of 0.5° covering upto θ = 28.45° with 99.8% completeness accomplished.

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
C1	0.74584 (13)	1.08296 (13)	0.93414 (13)	0.0208 (2)
H1A	0.6562	1.118	0.9193	0.031*
H1B	0.8195	1.1223	0.8942	0.031*
H1C	0.7685	1.1225	1.0431	0.031*
C2	0.87462 (12)	0.84588 (14)	0.86348 (14)	0.0241 (2)
H2A	0.9444	0.8772	0.8132	0.036*
H2B	0.8629	0.7322	0.8145	0.036*
H2C	0.9061	0.8896	0.9712	0.036*
C3	0.61532 (13)	0.83957 (14)	0.90149 (13)	0.0222 (2)
H3A	0.6156	0.7262	0.8517	0.033*
H3B	0.5263	0.8661	0.8736	0.033*
H3C	0.627	0.8836	1.0122	0.033*
C4	0.73538 (11)	0.90605 (13)	0.85019 (12)	0.0165 (2)
C5	0.68030 (10)	0.71782 (12)	0.58068 (12)	0.0145 (2)
C6	0.63194 (11)	0.69956 (12)	0.42678 (12)	0.0151 (2)
H6	0.7064	0.7491	0.3939	0.018*
C7	0.49600 (11)	0.77696 (12)	0.43670 (12)	0.0152 (2)
H7	0.5149	0.891	0.5094	0.018*
C8	0.44465 (12)	0.75423 (15)	0.28179 (13)	0.0223 (2)
H8A	0.3603	0.8085	0.2919	0.033*
H8B	0.4228	0.643	0.2101	0.033*
H8C	0.5178	0.7965	0.2438	0.033*
C9	0.12195 (11)	0.73713 (13)	0.43575 (12)	0.0166 (2)
C10	0.05152 (11)	0.58888 (13)	0.37062 (13)	0.0177 (2)
H10	0.0739	0.5198	0.4067	0.021*
C11	−0.05154 (11)	0.54303 (14)	0.25272 (13)	0.0197 (2)
H11	−0.0984	0.4414	0.2071	0.024*
C12	−0.08741 (11)	0.64442 (15)	0.19995 (13)	0.0209 (2)
C13	−0.01768 (12)	0.79315 (15)	0.26927 (14)	0.0233 (2)
H13	−0.0425	0.8639	0.2362	0.028*
C14	0.08753 (12)	0.84021 (14)	0.38584 (14)	0.0215 (2)
H14	0.1352	0.9413	0.4308	0.026*
C15	−0.19933 (13)	0.59239 (18)	0.07100 (15)	0.0296 (3)
H15A	−0.1592	0.5302	−0.0263	0.044*
H15B	−0.2358	0.6838	0.0733	0.044*
H15C	−0.2756	0.5295	0.0824	0.044*
N1	0.39695 (9)	0.71013 (11)	0.50168 (10)	0.01484 (18)
O1	0.70108 (8)	0.86607 (8)	0.68847 (8)	0.01528 (15)
O2	0.69788 (8)	0.60683 (9)	0.59739 (9)	0.01913 (17)
O3	0.60741 (8)	0.53975 (9)	0.31707 (9)	0.01922 (17)
H3	0.6564	0.4879	0.3431	0.029*
O4	0.21687 (9)	0.71817 (10)	0.66814 (9)	0.02355 (18)
O5	0.29082 (9)	0.95624 (10)	0.65376 (10)	0.02641 (19)
S1	0.25877 (3)	0.79036 (3)	0.58022 (3)	0.01691 (8)
H1D	0.3859 (16)	0.6124 (18)	0.4581 (17)	0.025 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0283 (6)	0.0164 (5)	0.0150 (5)	−0.0004 (4)	−0.0005 (4)	0.0059 (4)
C2	0.0216 (5)	0.0238 (6)	0.0233 (6)	0.0015 (4)	−0.0067 (4)	0.0095 (5)
C3	0.0261 (6)	0.0222 (5)	0.0196 (5)	0.0003 (4)	0.0039 (4)	0.0114 (5)
C4	0.0196 (5)	0.0169 (5)	0.0124 (5)	0.0001 (4)	−0.0021 (4)	0.0072 (4)
C5	0.0108 (4)	0.0148 (5)	0.0162 (5)	0.0007 (4)	0.0006 (4)	0.0065 (4)
C6	0.0152 (5)	0.0141 (5)	0.0140 (5)	0.0003 (4)	0.0008 (4)	0.0055 (4)
C7	0.0159 (5)	0.0144 (5)	0.0160 (5)	0.0000 (4)	−0.0002 (4)	0.0083 (4)
C8	0.0221 (5)	0.0290 (6)	0.0201 (5)	0.0010 (4)	−0.0021 (4)	0.0159 (5)
C9	0.0138 (5)	0.0186 (5)	0.0178 (5)	0.0042 (4)	0.0029 (4)	0.0088 (4)
C10	0.0153 (5)	0.0201 (5)	0.0206 (5)	0.0044 (4)	0.0031 (4)	0.0119 (4)
C11	0.0152 (5)	0.0230 (5)	0.0211 (5)	0.0016 (4)	0.0018 (4)	0.0112 (5)
C12	0.0135 (5)	0.0337 (6)	0.0211 (5)	0.0060 (4)	0.0051 (4)	0.0171 (5)
C13	0.0196 (5)	0.0310 (6)	0.0306 (6)	0.0089 (5)	0.0064 (5)	0.0229 (5)
C14	0.0192 (5)	0.0197 (5)	0.0287 (6)	0.0046 (4)	0.0042 (4)	0.0140 (5)
C15	0.0204 (6)	0.0507 (8)	0.0263 (6)	0.0044 (5)	0.0003 (5)	0.0256 (6)
N1	0.0145 (4)	0.0121 (4)	0.0174 (4)	0.0014 (3)	0.0016 (3)	0.0068 (4)
O1	0.0187 (4)	0.0130 (3)	0.0129 (3)	0.0001 (3)	−0.0015 (3)	0.0058 (3)
O2	0.0199 (4)	0.0148 (4)	0.0221 (4)	0.0016 (3)	−0.0027 (3)	0.0090 (3)
O3	0.0220 (4)	0.0143 (4)	0.0157 (4)	0.0026 (3)	−0.0009 (3)	0.0031 (3)
O4	0.0227 (4)	0.0316 (5)	0.0163 (4)	0.0011 (3)	0.0028 (3)	0.0118 (4)
O5	0.0257 (4)	0.0159 (4)	0.0268 (4)	0.0034 (3)	0.0006 (3)	0.0022 (3)
S1	0.01644 (13)	0.01627 (13)	0.01483 (13)	0.00257 (9)	0.00163 (9)	0.00506 (10)

Geometric parameters (Å, º) top

C1—C4	1.5218 (15)	C8—H8B	0.98
C1—H1A	0.98	C8—H8C	0.98
C1—H1B	0.98	C9—C14	1.3921 (15)
C1—H1C	0.98	C9—C10	1.3949 (15)
C2—C4	1.5235 (15)	C9—S1	1.7733 (11)
C2—H2A	0.98	C10—C11	1.3881 (15)
C2—H2B	0.98	C10—H10	0.95
C2—H2C	0.98	C11—C12	1.4012 (16)
C3—C4	1.5245 (16)	C11—H11	0.95
C3—H3A	0.98	C12—C13	1.3938 (18)
C3—H3B	0.98	C12—C15	1.5106 (16)
C3—H3C	0.98	C13—C14	1.3914 (17)
C4—O1	1.4978 (12)	C13—H13	0.95
C5—O2	1.2115 (13)	C14—H14	0.95
C5—O1	1.3277 (12)	C15—H15A	0.98
C5—C6	1.5244 (14)	C15—H15B	0.98
C6—O3	1.4161 (12)	C15—H15C	0.98
C6—C7	1.5353 (14)	N1—S1	1.6172 (9)
C6—H6	1	N1—H1D	0.842 (16)
C7—N1	1.4750 (13)	O3—H3	0.84
C7—C8	1.5245 (15)	O4—S1	1.4422 (9)
C7—H7	1	O5—S1	1.4393 (9)
C8—H8A	0.98

C4—C1—H1A	109.5	C7—C8—H8B	109.5
C4—C1—H1B	109.5	H8A—C8—H8B	109.5
H1A—C1—H1B	109.5	C7—C8—H8C	109.5
C4—C1—H1C	109.5	H8A—C8—H8C	109.5
H1A—C1—H1C	109.5	H8B—C8—H8C	109.5
H1B—C1—H1C	109.5	C14—C9—C10	120.57 (10)
C4—C2—H2A	109.5	C14—C9—S1	120.59 (9)
C4—C2—H2B	109.5	C10—C9—S1	118.82 (8)
H2A—C2—H2B	109.5	C11—C10—C9	119.49 (10)
C4—C2—H2C	109.5	C11—C10—H10	120.3
H2A—C2—H2C	109.5	C9—C10—H10	120.3
H2B—C2—H2C	109.5	C10—C11—C12	120.95 (11)
C4—C3—H3A	109.5	C10—C11—H11	119.5
C4—C3—H3B	109.5	C12—C11—H11	119.5
H3A—C3—H3B	109.5	C13—C12—C11	118.43 (10)
C4—C3—H3C	109.5	C13—C12—C15	121.30 (11)
H3A—C3—H3C	109.5	C11—C12—C15	120.27 (11)
H3B—C3—H3C	109.5	C14—C13—C12	121.41 (10)
O1—C4—C1	102.44 (8)	C14—C13—H13	119.3
O1—C4—C2	109.60 (9)	C12—C13—H13	119.3
C1—C4—C2	111.41 (9)	C13—C14—C9	119.13 (11)
O1—C4—C3	108.99 (9)	C13—C14—H14	120.4
C1—C4—C3	111.22 (9)	C9—C14—H14	120.4
C2—C4—C3	112.66 (10)	C12—C15—H15A	109.5
O2—C5—O1	125.85 (10)	C12—C15—H15B	109.5
O2—C5—C6	122.05 (9)	H15A—C15—H15B	109.5
O1—C5—C6	112.09 (9)	C12—C15—H15C	109.5
O3—C6—C5	109.87 (8)	H15A—C15—H15C	109.5
O3—C6—C7	108.58 (8)	H15B—C15—H15C	109.5
C5—C6—C7	110.83 (8)	C7—N1—S1	123.52 (7)
O3—C6—H6	109.2	C7—N1—H1D	116.2 (10)
C5—C6—H6	109.2	S1—N1—H1D	112.5 (10)
C7—C6—H6	109.2	C5—O1—C4	119.50 (8)
N1—C7—C8	114.28 (9)	C6—O3—H3	109.5
N1—C7—C6	105.79 (8)	O5—S1—O4	120.06 (5)
C8—C7—C6	110.98 (9)	O5—S1—N1	107.61 (5)
N1—C7—H7	108.5	O4—S1—N1	105.57 (5)
C8—C7—H7	108.5	O5—S1—C9	108.09 (5)
C6—C7—H7	108.5	O4—S1—C9	106.33 (5)
C7—C8—H8A	109.5	N1—S1—C9	108.80 (5)

O2—C5—C6—O3	2.43 (14)	S1—C9—C14—C13	178.17 (9)
O1—C5—C6—O3	−178.31 (8)	C8—C7—N1—S1	−76.81 (11)
O2—C5—C6—C7	122.43 (11)	C6—C7—N1—S1	160.79 (7)
O1—C5—C6—C7	−58.31 (11)	O2—C5—O1—C4	−6.69 (15)
O3—C6—C7—N1	67.16 (10)	C6—C5—O1—C4	174.08 (8)
C5—C6—C7—N1	−53.61 (11)	C1—C4—O1—C5	−178.29 (9)
O3—C6—C7—C8	−57.32 (11)	C2—C4—O1—C5	63.33 (12)
C5—C6—C7—C8	−178.09 (9)	C3—C4—O1—C5	−60.39 (12)
C14—C9—C10—C11	1.46 (16)	C7—N1—S1—O5	−33.34 (10)
S1—C9—C10—C11	−177.12 (8)	C7—N1—S1—O4	−162.69 (8)
C9—C10—C11—C12	−1.07 (17)	C7—N1—S1—C9	83.54 (9)
C10—C11—C12—C13	−0.37 (17)	C14—C9—S1—O5	15.26 (11)
C10—C11—C12—C15	179.70 (10)	C10—C9—S1—O5	−166.16 (9)
C11—C12—C13—C14	1.47 (17)	C14—C9—S1—O4	145.40 (9)
C15—C12—C13—C14	−178.60 (11)	C10—C9—S1—O4	−36.01 (10)
C12—C13—C14—C9	−1.10 (18)	C14—C9—S1—N1	−101.32 (10)
C10—C9—C14—C13	−0.39 (17)	C10—C9—S1—N1	77.26 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2ⁱ	0.842 (16)	2.059 (16)	2.8625 (12)	159.5 (14)
O3—H3···O4ⁱ	0.84	2.40	3.2041 (12)	162
C1—H1C···O4ⁱⁱ	0.98	2.54	3.4936 (14)	164

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

Experimental details

Crystal data
Chemical formula	C₁₅H₂₃NO₅S
M_r	329.4
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.6038 (8), 9.9059 (8), 10.1064 (11)
α, β, γ (°)	119.342 (2), 92.307 (2), 93.422 (2)
V (Å³)	833.95 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.22 × 0.18 × 0.14

Data collection
Diffractometer	Bruker X8 APEXII 4K Kappa CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.954, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	24635, 4192, 3712
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.083, 1.05
No. of reflections	4192
No. of parameters	209
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SAINT-Plus and XPREP (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005) and ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2ⁱ	0.842 (16)	2.059 (16)	2.8625 (12)	159.5 (14)
O3—H3···O4ⁱ	0.84	2.40	3.2041 (12)	162
C1—H1C···O4ⁱⁱ	0.98	2.54	3.4936 (14)	164

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

Acknowledgements

Financial assistance from Mintek and THRIP is gratefully acknowledged.

References

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