cis-N-(2-Hydroxy­cyclo­hexyl)-p-toluene­sulfonamide

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

doi:10.1107/S1600536810002151

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o463

https://doi.org/10.1107/S1600536810002151

Open

access

cis-N-(2-Hydroxycyclohexyl)-p-toluenesulfonamide

Mohamed I. Fadlalla,^a Holger B. Friedrich,^a Glenn E. M. Maguire ^a and Muhammad D. Bala ^a ^*

^aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: bala@ukzn.ac.za

(Received 26 November 2009; accepted 18 January 2010; online 27 January 2010)

There are two symmetry-independent molecules in the asymmetric unit of the title compound, C₁₃H₁₉NO₃S. The cyclohexane rings in the two molecules adopt chair configurations. The hydroxy and amino groups on the cyclohexane ring assume axial and equatorial orientations, respectively, with respect to the plane of the ring. The crystal structure is stabilized by two intermolecular N—H⋯O and O—H⋯O hydrogen bonds from the two symmetry-independent molecules.

Related literature

For related structures of β-amino alcohols, see: Bergmeier (2000 ); Krzemiński & Wojtczak (2005 ). For related structures of tosylamino compounds, see: Coote et al. (2008 ); Liu et al. (2005 ); Chinnakali et al. (2007 ); Nan & Xing (2006 ). For the synthesis of the title compound, see: Naiker et al. (2008 ).

Experimental

Crystal data

C₁₃H₁₉NO₃S
M_r = 269.35
Triclinic, $[P \overline 1]$
a = 6.3031 (1) Å
b = 12.8355 (2) Å
c = 17.5367 (3) Å
α = 106.645 (1)°
β = 93.971 (1)°
γ = 100.047 (1)°
V = 1327.75 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.51 × 0.31 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
18458 measured reflections
6423 independent reflections
4837 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.111
S = 1.07
6423 reflections
343 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O6ⁱ	0.83 (2)	2.00 (2)	2.8255 (17)	175.0 (18)
N2—H2N⋯O3ⁱⁱ	0.82 (2)	2.00 (2)	2.8155 (18)	173.1 (19)
O3—H3O⋯O5ⁱⁱⁱ	0.83 (2)	1.93 (2)	2.7489 (15)	171 (2)
O6—H6O⋯O2^iv	0.83 (2)	1.98 (2)	2.8001 (15)	169 (2)
Symmetry codes: (i) x-1, y-1, z; (ii) x+1, y+1, z; (iii) x, y-1, z; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810002151/lx2131sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002151/lx2131Isup2.hkl

checkCIF report

Comment top

Molecules containing a β-amino alcohol system have been used as precursors for the synthesis of chiral ligands, aziridine and biologically active compounds (Bergmeier, 2000; Krzemiński & Wojtczak, 2005). As a part of study on this family of compounds, we report the crystal structure of the title compound (l) (Fig. 1).

The geometry of the benzenesulfonamide unit in (I) agrees with that for related structures (Chinnakali et al. 2007; Nan & Xing, 2006). The cyclohexane rings in the two molecules adopt the chair configuration. The hydroxy and amino groups on the cyclohexane ring respectively assume axial and equatorial orientations with respect to the plane of the ring. The crystal packing (Fig. 2) is stabilized by intermolecular N—H···O and O—H···O hydrogen bonds from the two neighbouring symmetry-independent molecules (Table 1).

Related literature top

For related structures of β-amino alcohol, see: Bergmeier (2000); Krzemiński & Wojtczak (2005). For related structures of tosylamino compounds, see: Coote et al. (2008); Liu et al. (2005); Chinnakali et al. (2007); Nan & Xing (2006). For the synthesis of the title compound, see: Naiker et al. (2008).

Experimental top

The synthesis of the title compound was carried out using a modified literature method (Naiker et al. 2008) using a catalytic process. To a nitrogen saturated Schlenk tube, toluene (6 ml), water (172 µl) chloroamine-T (0.21 g, 0.956 mmol), cyclohexene (0.478 mmol) and catalyst (0.03 g) were added in that order. After the complete conversion of the starting material the catalyst was gravity filtered. The reaction mixture was washed with 15 ml of sodium sulfite (1 g in 15 ml of de-ionized water), followed by 15 ml of ethyl acetate. Then the aqueous layer was separated from the organic layer and washed further with 3 × 15 ml of ethyl acetate. The solvent was removed in vacuo, and the crude product was purified using preparative high pressure liquid chromatography to yield the title compound as a white solid. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in acetonitrile/water (1:1 v/v) at room temperature. (mp; 414–416 K) Spectroscopic analysis: ¹³C NMR (400 MHz, CDCl₃, δ, p.p.m): = 19.76 (s, 1 C), 21.54 (s, 2 C), 27.98 (s, 1 C), 31.46(s, 1 C), 55.10 (s, 1 C), 68.76 (s, 1 C), 126.97 (s, 2 C), 129.74 (s, 2 C), 137.98(s, 1 C), 143.39 (s, 143.39).. MS m/z –[fragment]–(%): 291.8 (M + Na⁺) calculated = 291.8 for C₁₃H₁₉NO₃SNa⁺.

FT–IR (cm^-1): = 3414(m), (OH), 3137(m), (NH), 2938(w), 2849(w), 1598(m), (ar), 1059(m), (S=O).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50 % probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. N—H···O and O—H···O hydrogen bonding interactions (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) x - 1, y - 1, z; (ii) x + 1, y + 1, z; (iii) x, y - 1, z; (iv) x, y + 1, z; (v) x + 1, y + 1, z; (vi) x - 1, y - 1, z; (vii) x, y + 1, z; (viii) x, y - 1, z.]

cis-N-(2-Hydroxycyclohexyl)-p-toluenesulfonamide cis-2-Tosylaminocyclohexanol top

Crystal data top

C₁₃H₁₉NO₃S	Z = 4
M_r = 269.35	F(000) = 576
Triclinic, P1	D_x = 1.347 Mg m⁻³
Hall symbol: -P 1	Melting point = 414–416 K
a = 6.3031 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.8355 (2) Å	Cell parameters from 6946 reflections
c = 17.5367 (3) Å	θ = 2.4–28.3°
α = 106.645 (1)°	µ = 0.24 mm⁻¹
β = 93.971 (1)°	T = 173 K
γ = 100.047 (1)°	Block, colourless
V = 1327.75 (4) Å³	0.51 × 0.31 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	4837 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 28.0°, θ_min = 1.2°
φ and ω scans	h = −8→8
18458 measured reflections	k = −16→16
6423 independent reflections	l = −23→23

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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0582P)² + 0.0739P] where P = (F_o² + 2F_c²)/3
6423 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₃H₁₉NO₃S	γ = 100.047 (1)°
M_r = 269.35	V = 1327.75 (4) Å³
Triclinic, P1	Z = 4
a = 6.3031 (1) Å	Mo Kα radiation
b = 12.8355 (2) Å	µ = 0.24 mm⁻¹
c = 17.5367 (3) Å	T = 173 K
α = 106.645 (1)°	0.51 × 0.31 × 0.25 mm
β = 93.971 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4837 reflections with I > 2σ(I)
18458 measured reflections	R_int = 0.033
6423 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.40 e Å⁻³
6423 reflections	Δρ_min = −0.41 e Å⁻³
343 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
C1	0.3149 (2)	0.39725 (12)	0.35318 (8)	0.0230 (3)
H1	0.4155	0.4675	0.3860	0.028*
C2	0.4327 (2)	0.30139 (12)	0.34741 (9)	0.0227 (3)
H2	0.5706	0.3156	0.3236	0.027*
C3	0.4842 (3)	0.28788 (14)	0.42986 (9)	0.0303 (4)
H3A	0.5896	0.3543	0.4639	0.036*
H3B	0.5522	0.2225	0.4240	0.036*
C4	0.2795 (3)	0.27272 (15)	0.47095 (10)	0.0344 (4)
H4A	0.1800	0.2022	0.4399	0.041*
H4B	0.3195	0.2684	0.5254	0.041*
C5	0.1644 (3)	0.36911 (14)	0.47692 (9)	0.0337 (4)
H5A	0.2583	0.4384	0.5127	0.040*
H5B	0.0285	0.3557	0.5009	0.040*
C6	0.1107 (3)	0.38351 (13)	0.39456 (9)	0.0266 (3)
H6A	0.0034	0.3178	0.3607	0.032*
H6B	0.0449	0.4497	0.4010	0.032*
C7	0.3445 (2)	0.63056 (12)	0.29981 (8)	0.0212 (3)
C8	0.5061 (2)	0.72537 (12)	0.31511 (9)	0.0238 (3)
H8	0.6421	0.7204	0.2956	0.029*
C9	0.4672 (3)	0.82718 (12)	0.35906 (9)	0.0282 (3)
H9	0.5775	0.8920	0.3693	0.034*
C10	0.2692 (3)	0.83612 (13)	0.38840 (9)	0.0290 (4)
C11	0.1103 (3)	0.74045 (14)	0.37164 (10)	0.0310 (4)
H11	−0.0257	0.7454	0.3911	0.037*
C12	0.1439 (3)	0.63787 (13)	0.32735 (9)	0.0284 (3)
H12	0.0320	0.5735	0.3159	0.034*
C13	0.2270 (4)	0.94682 (16)	0.43611 (11)	0.0459 (5)
H13A	0.0900	0.9582	0.4130	0.069*
H13B	0.3460	1.0061	0.4345	0.069*
H13C	0.2173	0.9480	0.4919	0.069*
N1	0.2596 (2)	0.40722 (10)	0.27298 (8)	0.0243 (3)
O1	0.30664 (19)	0.48034 (9)	0.15979 (6)	0.0319 (3)
O2	0.62179 (17)	0.50634 (9)	0.26023 (7)	0.0322 (3)
O3	0.29042 (18)	0.20373 (9)	0.29512 (6)	0.0262 (2)
S1	0.39239 (6)	0.50145 (3)	0.24179 (2)	0.02302 (10)
H1N	0.134 (3)	0.3817 (15)	0.2496 (11)	0.039 (5)*
H3O	0.364 (3)	0.1556 (18)	0.2813 (12)	0.050 (6)*
C14	0.7984 (3)	1.13220 (12)	0.14293 (9)	0.0260 (3)
H14	0.6960	1.0621	0.1109	0.031*
C15	0.6821 (2)	1.22875 (12)	0.14932 (8)	0.0221 (3)
H15	0.5435	1.2142	0.1726	0.026*
C16	0.6321 (3)	1.24306 (13)	0.06696 (9)	0.0275 (3)
H16A	0.5649	1.3087	0.0729	0.033*
H16B	0.5267	1.1769	0.0325	0.033*
C17	0.8384 (3)	1.25814 (14)	0.02681 (9)	0.0311 (4)
H17A	0.8013	1.2657	−0.0269	0.037*
H17B	0.9405	1.3268	0.0594	0.037*
C18	0.9460 (3)	1.15881 (15)	0.01851 (10)	0.0382 (4)
H18A	1.0803	1.1699	−0.0068	0.046*
H18B	0.8468	1.0909	−0.0167	0.046*
C19	1.0017 (3)	1.14389 (14)	0.10043 (10)	0.0322 (4)
H19A	1.1115	1.2088	0.1339	0.039*
H19B	1.0647	1.0768	0.0934	0.039*
C20	0.7614 (2)	0.89890 (11)	0.20252 (8)	0.0214 (3)
C21	0.5911 (3)	0.82342 (12)	0.15054 (9)	0.0253 (3)
H21	0.4570	0.8445	0.1409	0.030*
C22	0.6186 (3)	0.71642 (13)	0.11252 (9)	0.0290 (3)
H22	0.5021	0.6643	0.0769	0.035*
C23	0.8145 (3)	0.68457 (12)	0.12593 (9)	0.0276 (3)
C24	0.9834 (3)	0.76236 (13)	0.17751 (9)	0.0276 (3)
H24	1.1182	0.7418	0.1867	0.033*
C25	0.9594 (3)	0.86956 (13)	0.21587 (9)	0.0260 (3)
H25	1.0767	0.9221	0.2508	0.031*
C26	0.8384 (3)	0.56743 (14)	0.08535 (11)	0.0414 (4)
H26A	0.7230	0.5151	0.0976	0.062*
H26B	0.9802	0.5569	0.1048	0.062*
H26C	0.8275	0.5541	0.0272	0.062*
N2	0.8567 (2)	1.12308 (11)	0.22299 (8)	0.0285 (3)
O4	0.81390 (19)	1.05591 (9)	0.33850 (6)	0.0326 (3)
O5	0.49416 (18)	1.02921 (9)	0.23866 (7)	0.0345 (3)
O6	0.82296 (18)	1.32622 (9)	0.20231 (6)	0.0246 (2)
S2	0.72262 (6)	1.03181 (3)	0.25663 (2)	0.02444 (11)
H2N	0.981 (3)	1.1520 (16)	0.2453 (11)	0.040 (6)*
H6O	0.751 (4)	1.3754 (19)	0.2141 (13)	0.061 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0245 (8)	0.0189 (7)	0.0237 (7)	0.0036 (6)	−0.0012 (6)	0.0050 (6)
C2	0.0177 (7)	0.0233 (7)	0.0270 (8)	0.0037 (6)	0.0014 (6)	0.0080 (6)
C3	0.0286 (9)	0.0345 (9)	0.0307 (8)	0.0111 (7)	−0.0005 (7)	0.0128 (7)
C4	0.0389 (10)	0.0442 (10)	0.0277 (8)	0.0158 (8)	0.0068 (7)	0.0177 (7)
C5	0.0375 (10)	0.0382 (9)	0.0257 (8)	0.0127 (8)	0.0057 (7)	0.0068 (7)
C6	0.0293 (9)	0.0256 (8)	0.0260 (8)	0.0117 (7)	0.0049 (6)	0.0054 (6)
C7	0.0221 (8)	0.0212 (7)	0.0237 (7)	0.0071 (6)	0.0046 (6)	0.0099 (6)
C8	0.0237 (8)	0.0256 (8)	0.0240 (7)	0.0051 (6)	0.0049 (6)	0.0099 (6)
C9	0.0337 (9)	0.0227 (8)	0.0275 (8)	0.0039 (7)	0.0026 (7)	0.0080 (6)
C10	0.0394 (10)	0.0282 (8)	0.0226 (8)	0.0152 (7)	0.0027 (7)	0.0080 (6)
C11	0.0286 (9)	0.0383 (9)	0.0344 (9)	0.0170 (7)	0.0114 (7)	0.0164 (7)
C12	0.0235 (8)	0.0280 (8)	0.0382 (9)	0.0074 (6)	0.0069 (7)	0.0153 (7)
C13	0.0564 (13)	0.0389 (10)	0.0413 (11)	0.0240 (9)	0.0051 (9)	0.0021 (8)
N1	0.0210 (7)	0.0224 (6)	0.0285 (7)	−0.0005 (5)	−0.0031 (5)	0.0106 (5)
O1	0.0401 (7)	0.0300 (6)	0.0254 (6)	0.0060 (5)	0.0061 (5)	0.0087 (5)
O2	0.0210 (6)	0.0244 (6)	0.0502 (7)	0.0075 (5)	0.0079 (5)	0.0073 (5)
O3	0.0234 (6)	0.0204 (5)	0.0322 (6)	0.0070 (5)	0.0023 (5)	0.0026 (4)
S1	0.0216 (2)	0.01999 (19)	0.0284 (2)	0.00532 (14)	0.00508 (15)	0.00776 (15)
C14	0.0291 (8)	0.0184 (7)	0.0274 (8)	0.0021 (6)	−0.0020 (6)	0.0051 (6)
C15	0.0173 (7)	0.0232 (7)	0.0245 (7)	0.0023 (6)	0.0009 (6)	0.0069 (6)
C16	0.0258 (8)	0.0306 (8)	0.0256 (8)	0.0063 (7)	−0.0013 (6)	0.0084 (6)
C17	0.0329 (9)	0.0383 (9)	0.0236 (8)	0.0084 (7)	0.0055 (6)	0.0106 (7)
C18	0.0422 (11)	0.0415 (10)	0.0282 (9)	0.0140 (8)	0.0095 (8)	0.0022 (7)
C19	0.0356 (10)	0.0278 (8)	0.0343 (9)	0.0167 (7)	0.0075 (7)	0.0045 (7)
C20	0.0232 (8)	0.0187 (7)	0.0243 (7)	0.0055 (6)	0.0056 (6)	0.0085 (6)
C21	0.0230 (8)	0.0252 (8)	0.0289 (8)	0.0071 (6)	0.0026 (6)	0.0090 (6)
C22	0.0328 (9)	0.0240 (8)	0.0274 (8)	0.0046 (7)	0.0011 (7)	0.0048 (6)
C23	0.0380 (9)	0.0250 (8)	0.0261 (8)	0.0130 (7)	0.0150 (7)	0.0112 (6)
C24	0.0256 (8)	0.0324 (8)	0.0333 (8)	0.0140 (7)	0.0107 (6)	0.0167 (7)
C25	0.0219 (8)	0.0279 (8)	0.0302 (8)	0.0050 (6)	0.0033 (6)	0.0119 (6)
C26	0.0559 (13)	0.0276 (9)	0.0450 (11)	0.0177 (8)	0.0194 (9)	0.0092 (8)
N2	0.0258 (8)	0.0223 (7)	0.0366 (8)	−0.0015 (6)	−0.0052 (6)	0.0133 (6)
O4	0.0412 (7)	0.0254 (6)	0.0288 (6)	0.0038 (5)	0.0057 (5)	0.0059 (5)
O5	0.0235 (6)	0.0230 (6)	0.0539 (8)	0.0081 (5)	0.0060 (5)	0.0047 (5)
O6	0.0234 (6)	0.0209 (5)	0.0268 (6)	0.0066 (5)	0.0010 (4)	0.0023 (4)
S2	0.0242 (2)	0.01775 (18)	0.0308 (2)	0.00465 (15)	0.00403 (15)	0.00618 (15)

Geometric parameters (Å, º) top

C1—N1	1.472 (2)	C14—N2	1.4690 (19)
C1—C2	1.528 (2)	C14—C15	1.528 (2)
C1—C6	1.529 (2)	C14—C19	1.532 (2)
C1—H1	1.0000	C14—H14	1.0000
C2—O3	1.4325 (17)	C15—O6	1.4316 (17)
C2—C3	1.525 (2)	C15—C16	1.526 (2)
C2—H2	1.0000	C15—H15	1.0000
C3—C4	1.531 (2)	C16—C17	1.530 (2)
C3—H3A	0.9900	C16—H16A	0.9900
C3—H3B	0.9900	C16—H16B	0.9900
C4—C5	1.522 (2)	C17—C18	1.522 (2)
C4—H4A	0.9900	C17—H17A	0.9900
C4—H4B	0.9900	C17—H17B	0.9900
C5—C6	1.530 (2)	C18—C19	1.528 (2)
C5—H5A	0.9900	C18—H18A	0.9900
C5—H5B	0.9900	C18—H18B	0.9900
C6—H6A	0.9900	C19—H19A	0.9900
C6—H6B	0.9900	C19—H19B	0.9900
C7—C8	1.390 (2)	C20—C21	1.385 (2)
C7—C12	1.393 (2)	C20—C25	1.389 (2)
C7—S1	1.7674 (14)	C20—S2	1.7665 (14)
C8—C9	1.387 (2)	C21—C22	1.391 (2)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.393 (2)	C22—C23	1.392 (2)
C9—H9	0.9500	C22—H22	0.9500
C10—C11	1.386 (2)	C23—C24	1.388 (2)
C10—C13	1.507 (2)	C23—C26	1.507 (2)
C11—C12	1.384 (2)	C24—C25	1.387 (2)
C11—H11	0.9500	C24—H24	0.9500
C12—H12	0.9500	C25—H25	0.9500
C13—H13A	0.9800	C26—H26A	0.9800
C13—H13B	0.9800	C26—H26B	0.9800
C13—H13C	0.9800	C26—H26C	0.9800
N1—S1	1.5975 (13)	N2—S2	1.5982 (13)
N1—H1N	0.83 (2)	N2—H2N	0.82 (2)
O1—S1	1.4322 (11)	O4—S2	1.4343 (12)
O2—S1	1.4461 (11)	O5—S2	1.4452 (12)
O3—H3O	0.83 (2)	O6—H6O	0.83 (2)

N1—C1—C2	110.49 (11)	N2—C14—C15	110.28 (12)
N1—C1—C6	110.35 (12)	N2—C14—C19	109.93 (13)
C2—C1—C6	111.65 (12)	C15—C14—C19	112.15 (12)
N1—C1—H1	108.1	N2—C14—H14	108.1
C2—C1—H1	108.1	C15—C14—H14	108.1
C6—C1—H1	108.1	C19—C14—H14	108.1
O3—C2—C3	110.68 (12)	O6—C15—C16	110.75 (12)
O3—C2—C1	106.45 (11)	O6—C15—C14	107.06 (11)
C3—C2—C1	110.94 (12)	C16—C15—C14	110.71 (12)
O3—C2—H2	109.6	O6—C15—H15	109.4
C3—C2—H2	109.6	C16—C15—H15	109.4
C1—C2—H2	109.6	C14—C15—H15	109.4
C2—C3—C4	111.59 (13)	C15—C16—C17	111.19 (13)
C2—C3—H3A	109.3	C15—C16—H16A	109.4
C4—C3—H3A	109.3	C17—C16—H16A	109.4
C2—C3—H3B	109.3	C15—C16—H16B	109.4
C4—C3—H3B	109.3	C17—C16—H16B	109.4
H3A—C3—H3B	108.0	H16A—C16—H16B	108.0
C5—C4—C3	110.62 (14)	C18—C17—C16	110.11 (14)
C5—C4—H4A	109.5	C18—C17—H17A	109.6
C3—C4—H4A	109.5	C16—C17—H17A	109.6
C5—C4—H4B	109.5	C18—C17—H17B	109.6
C3—C4—H4B	109.5	C16—C17—H17B	109.6
H4A—C4—H4B	108.1	H17A—C17—H17B	108.2
C4—C5—C6	111.54 (13)	C17—C18—C19	110.83 (13)
C4—C5—H5A	109.3	C17—C18—H18A	109.5
C6—C5—H5A	109.3	C19—C18—H18A	109.5
C4—C5—H5B	109.3	C17—C18—H18B	109.5
C6—C5—H5B	109.3	C19—C18—H18B	109.5
H5A—C5—H5B	108.0	H18A—C18—H18B	108.1
C1—C6—C5	110.98 (13)	C18—C19—C14	110.71 (14)
C1—C6—H6A	109.4	C18—C19—H19A	109.5
C5—C6—H6A	109.4	C14—C19—H19A	109.5
C1—C6—H6B	109.4	C18—C19—H19B	109.5
C5—C6—H6B	109.4	C14—C19—H19B	109.5
H6A—C6—H6B	108.0	H19A—C19—H19B	108.1
C8—C7—C12	120.34 (14)	C21—C20—C25	120.81 (14)
C8—C7—S1	119.33 (11)	C21—C20—S2	119.75 (11)
C12—C7—S1	120.29 (11)	C25—C20—S2	119.36 (11)
C9—C8—C7	119.46 (14)	C20—C21—C22	119.29 (14)
C9—C8—H8	120.3	C20—C21—H21	120.4
C7—C8—H8	120.3	C22—C21—H21	120.4
C8—C9—C10	121.16 (15)	C21—C22—C23	120.93 (15)
C8—C9—H9	119.4	C21—C22—H22	119.5
C10—C9—H9	119.4	C23—C22—H22	119.5
C11—C10—C9	118.17 (14)	C24—C23—C22	118.55 (14)
C11—C10—C13	120.69 (16)	C24—C23—C26	121.60 (15)
C9—C10—C13	121.13 (16)	C22—C23—C26	119.84 (16)
C12—C11—C10	121.93 (15)	C25—C24—C23	121.41 (14)
C12—C11—H11	119.0	C25—C24—H24	119.3
C10—C11—H11	119.0	C23—C24—H24	119.3
C11—C12—C7	118.92 (15)	C24—C25—C20	119.00 (14)
C11—C12—H12	120.5	C24—C25—H25	120.5
C7—C12—H12	120.5	C20—C25—H25	120.5
C10—C13—H13A	109.5	C23—C26—H26A	109.5
C10—C13—H13B	109.5	C23—C26—H26B	109.5
H13A—C13—H13B	109.5	H26A—C26—H26B	109.5
C10—C13—H13C	109.5	C23—C26—H26C	109.5
H13A—C13—H13C	109.5	H26A—C26—H26C	109.5
H13B—C13—H13C	109.5	H26B—C26—H26C	109.5
C1—N1—S1	122.50 (10)	C14—N2—S2	122.76 (11)
C1—N1—H1N	119.7 (13)	C14—N2—H2N	117.8 (13)
S1—N1—H1N	113.8 (13)	S2—N2—H2N	116.7 (13)
C2—O3—H3O	107.3 (15)	C15—O6—H6O	107.3 (16)
O1—S1—O2	118.31 (7)	O4—S2—O5	119.25 (7)
O1—S1—N1	107.26 (7)	O4—S2—N2	106.51 (7)
O2—S1—N1	108.38 (7)	O5—S2—N2	107.95 (7)
O1—S1—C7	109.32 (7)	O4—S2—C20	108.22 (7)
O2—S1—C7	105.55 (7)	O5—S2—C20	105.34 (7)
N1—S1—C7	107.60 (7)	N2—S2—C20	109.34 (7)

N1—C1—C2—O3	−57.65 (14)	N2—C14—C15—O6	56.00 (15)
C6—C1—C2—O3	65.57 (15)	C19—C14—C15—O6	−66.87 (15)
N1—C1—C2—C3	−178.14 (12)	N2—C14—C15—C16	176.81 (12)
C6—C1—C2—C3	−54.92 (16)	C19—C14—C15—C16	53.94 (16)
O3—C2—C3—C4	−62.41 (17)	O6—C15—C16—C17	62.91 (16)
C1—C2—C3—C4	55.53 (17)	C14—C15—C16—C17	−55.68 (16)
C2—C3—C4—C5	−56.05 (19)	C15—C16—C17—C18	58.13 (18)
C3—C4—C5—C6	55.88 (19)	C16—C17—C18—C19	−58.33 (19)
N1—C1—C6—C5	178.09 (12)	C17—C18—C19—C14	56.40 (19)
C2—C1—C6—C5	54.80 (16)	N2—C14—C19—C18	−177.42 (13)
C4—C5—C6—C1	−55.44 (18)	C15—C14—C19—C18	−54.35 (17)
C12—C7—C8—C9	0.9 (2)	C25—C20—C21—C22	1.2 (2)
S1—C7—C8—C9	178.53 (11)	S2—C20—C21—C22	−175.50 (11)
C7—C8—C9—C10	0.2 (2)	C20—C21—C22—C23	−0.1 (2)
C8—C9—C10—C11	−0.8 (2)	C21—C22—C23—C24	−0.7 (2)
C8—C9—C10—C13	−179.95 (15)	C21—C22—C23—C26	178.69 (14)
C9—C10—C11—C12	0.2 (2)	C22—C23—C24—C25	0.6 (2)
C13—C10—C11—C12	179.39 (15)	C26—C23—C24—C25	−178.82 (14)
C10—C11—C12—C7	0.9 (2)	C23—C24—C25—C20	0.4 (2)
C8—C7—C12—C11	−1.5 (2)	C21—C20—C25—C24	−1.3 (2)
S1—C7—C12—C11	−179.05 (12)	S2—C20—C25—C24	175.38 (11)
C2—C1—N1—S1	−103.58 (13)	C15—C14—N2—S2	102.29 (14)
C6—C1—N1—S1	132.45 (12)	C19—C14—N2—S2	−133.55 (12)
C1—N1—S1—O1	175.08 (11)	C14—N2—S2—O4	−174.30 (12)
C1—N1—S1—O2	46.28 (13)	C14—N2—S2—O5	−45.13 (14)
C1—N1—S1—C7	−67.40 (13)	C14—N2—S2—C20	68.98 (14)
C8—C7—S1—O1	−95.15 (13)	C21—C20—S2—O4	134.13 (12)
C12—C7—S1—O1	82.45 (13)	C25—C20—S2—O4	−42.57 (13)
C8—C7—S1—O2	33.11 (14)	C21—C20—S2—O5	5.55 (14)
C12—C7—S1—O2	−149.29 (12)	C25—C20—S2—O5	−171.15 (11)
C8—C7—S1—N1	148.68 (12)	C21—C20—S2—N2	−110.23 (12)
C12—C7—S1—N1	−33.72 (14)	C25—C20—S2—N2	73.07 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6ⁱ	0.83 (2)	2.00 (2)	2.8255 (17)	175.0 (18)
N2—H2N···O3ⁱⁱ	0.82 (2)	2.00 (2)	2.8155 (18)	173.1 (19)
O3—H3O···O5ⁱⁱⁱ	0.83 (2)	1.93 (2)	2.7489 (15)	171 (2)
O6—H6O···O2^iv	0.83 (2)	1.98 (2)	2.8001 (15)	169 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₉NO₃S
M_r	269.35
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	6.3031 (1), 12.8355 (2), 17.5367 (3)
α, β, γ (°)	106.645 (1), 93.971 (1), 100.047 (1)
V (Å³)	1327.75 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.51 × 0.31 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	18458, 6423, 4837
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.111, 1.07
No. of reflections	6423
No. of parameters	343
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.41

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O6ⁱ	0.83 (2)	2.00 (2)	2.8255 (17)	175.0 (18)
N2—H2N···O3ⁱⁱ	0.82 (2)	2.00 (2)	2.8155 (18)	173.1 (19)
O3—H3O···O5ⁱⁱⁱ	0.83 (2)	1.93 (2)	2.7489 (15)	171 (2)
O6—H6O···O2^iv	0.83 (2)	1.98 (2)	2.8001 (15)	169 (2)

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

Acknowledgements

We wish to thank Dr Manuel Fernandes (University of the Witwatersrand) for the data collection, and the NRF, THRIP and the University of KwaZulu-Natal for financial support.

References

Bergmeier, S. (2000). Tetrahedron, 56, 2561–2576. Web of Science CrossRef CAS Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chinnakali, K., Poornachandran, M., Raghunathan, R. & Fun, H.-K. (2007). Acta Cryst. E63, o1030–o1031. Web of Science CSD CrossRef IUCr Journals Google Scholar
Coote, S. C., O'Brien, P. & Whitwood, A. C. (2008). Org. Biomol. Chem. 6, 4299–4314. Web of Science CSD CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Krzemiński, M. P. & Wojtczak, A. (2005). Tetrahedron Lett. 46, 8299–8302. Google Scholar
Liu, Z., Fan, Y., Li, R., Zhou, B. & Wu, L. (2005). Tetrahedron Lett. 46, 1023–1025. Web of Science CSD CrossRef CAS Google Scholar
Naiker, T., Datye, A. & Friedrich, H. B. (2008). Appl. Catal. A, 350, 96–102. Google Scholar
Nan, Z.-H. & Xing, J.-D. (2006). Acta Cryst. E62, o1978–o1979. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar