research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages 757-759
doi:10.1107/S2056989015010233

Crystal structure of N,N-di­methyl-2-[(4-methyl­benz­yl)sulfon­yl]ethanamine

Alan R. Kennedy,a Abedawn I. Khalaf,a Fraser J. Scotta* and Colin J. Sucklinga

aWestchem, Department of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland
*Correspondence e-mail: fraser.j.scott@strath.ac.uk

Edited by H. Ishida, Okayama University, Japan (Received 8 May 2015; accepted 27 May 2015; online 6 June 2015)

In the crystal, the title compound, C12H19NO2S, has a disordered structure with two equally populated conformations of the amine fragment. A pair of weak C—H⋯O inter­molecular inter­actions between the CH2 and SO2 groups gives a one-dimensional supra­molecular structure that propagates through translation along the a-axis direction.

CCDC reference: 1403422

1. Chemical context

Parasitic helminths possess a number of evolutionary strategies that facilitate their co-existence with their host and, as such, up to one third of the global population may suffer from helminthetic infections (de Silva et al., 2003[Silva, N. R. de, Brooker, S., Hotez, P. J., Montresor, A., Engels, D. & Savioli, L. (2003). Trends Parasitol. 19, 547-551.]). These parasites can secrete immunomodulatory mol­ecules that prevent the parasites' clearance from the host without leaving the host vulnerable to opportunistic infections (Hewitson et al., 2009[Hewitson, J. P., Grainger, J. R. & Maizels, R. M. (2009). Mol. Biochem. Parasitol. 167, 1-11.]). ES-62 is one such immunomodulatory mol­ecule, a protein, which was discovered in the secretions of the rodent filarial nematode Acanthocheilonema and demonstrated to induce an anti-inflammatory immunological phenotype (Harnett et al., 1989[Harnett, W., Grainger, M., Kapil, A., Worms, M. J. & Parkhouse, R. M. E. (1989). Parasitol. Today, 99, 229-239.]). ES-62 has been studied for its potential to treat human diseases relating to inflammation, for example collagen-induced arthritis or rheumatoid arthritis, and many positive outcomes have been demonstrated.

A number of the significant anti-inflammatory activities of ES-62 are associated with post-translational glycosyl­ation and subsequent esterification by phospho­rylcholine. However, ES-62 is an immunogenic protein and is thus unsuitable as a drug itself (Harnett & Harnett, 2009[Harnett, W. & Harnett, M. M. (2009). Adv. Exp. Med. Biol. 666, 88-94.]). We have sought to capitalize on the immuno­modulatory effects of ES-62 whilst avoiding its inherent undrugability through synthesizing a library of drug-like small mol­ecules based upon phospho­rylcholine, the active moiety of ES-62. A series of sulfone analogues (Fig. 1[link]) have proven to be of great significance in our investigations into collagen-induced arthritis. Despite the apparent simplicity of these mol­ecules, we are aware of no relevant crystallographic study. As such, and as the title compound is of particular inter­est to our ongoing work (Al-Riyami et al., 2013[Al-Riyami, L., Pineda, M. A., Rzepecka, J., Huggan, J. K., Khalaf, A. I., Suckling, C. J., Scott, F. J., Rodgers, D. T., Harnett, M. M. & Harnett, W. (2013). J. Med. Chem. 56, 9982-10002.]), we report herein on the solid-state structure of the title compound.

[Scheme 1]
[Figure 1]
Figure 1
General structure of sulfone analogues. R represents alkyl chains and X represents halogen substituents.

2. Structural commentary

The mol­ecular structure of the title compound is shown in Fig. 2[link]. The amine group is disordered over two equally occupied sites such that the lone pair of the pyramidal N atom is anti to O1 with respect to the plane defined by C1—S1—C9 for the conformer containing N1 but syn for the N1A conformer.

[Figure 2]
Figure 2
The mol­ecular structure of the title compound with non-H atoms shown as 50% probability displacement ellipsoids. For the disordered fragment, the atoms labelled with the suffix `a' have been shown with hollow bonds whilst all other bonds are shown as solid lines.

3. Supra­molecular features

Neighbouring mol­ecules related by translation along the a-axis direction are connected by two weak C—H⋯O hydrogen bonds involving O1 and C1 and C9/C9A (Table 1[link] and Fig. 3[link]). This gives one-dimensional supra­molecular chains of mol­ecules that propagate parallel to the crystallographic a-axis direction.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1A⋯O1i 0.99 2.60 3.493 (2) 150
C9—H9A⋯O1i 0.99 2.49 3.415 (2) 155
C9A—H9C⋯O1i 0.99 2.61 3.415 (2) 138
Symmetry code: (i) x-1, y, z.
[Figure 3]
Figure 3
Part of the mol­ecular chain formed by translation along a highlighting the C—H⋯O contacts. Only one of the two disordered conformations is shown.

Other close inter­actions involve the disordered fragment. Thus the methyl group of C11A approaches the aromatic ring, giving a C—ċπ interaction [closest contact C6⋯C11A = 3.345 (5) Å] whilst C11 forms unfeasibly short inter­molecular inter­actions with its centrosymmetrically related self – an inter­action that is relieved by the observed disorder.

4. Synthesis and crystallization

A mixture of 2-[(4-methyl­benz­yl)sulfon­yl]ethyl methane­sulfonate and 1-methyl-4-[(vinyl­sulfon­yl)meth­yl]benzene (4.880 g) was dissolved in di­chloro­methane (50 ml, dry) to which di­methyl­amine (4 ml, 2M in THF) was added at room temperature with stirring. The stirring was continued at room temperature overnight. The reaction mixture was extracted with a saturated solution of sodium carbonate. The organic layer was collected, dried over MgSO4, filtered and the solvents were removed under reduced pressure and the crude product was applied to a silica gel column chromatography using first ethyl acetate/n-hexane (1/1, RF = 0.1) and then ethyl acetate/methanol (9/1). The product was obtained as a white solid which was recrystallized from ethyl acetate/n-hexane (2.200 g) (m.p. 341–343 K). HRESIMS: calculated for C12H19NO2S, 241.1136; found: 241.1139.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. Models where the site occupancy factors of the disordered groups were allowed to refine gave occupancies equal to 50%. So in the final model, occupancies of all the disordered atoms were set to this value. The C9—C10 and C9A—C10A distances were restrained to be 1.53 (1) Å. All H atoms were placed in idealized positions and were refined in riding modes with C—H equal to 0.95, 0.98 and 0.99 Å for CH, CH2 and CH3 groups, respectively, and Uiso(H) = 1.5Ueq(C) for methyl groups and 1.2Ueq(C) for all other groups.

Table 2
Experimental details

Crystal data
Chemical formula C12H19NO2S
Mr 241.34
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 123
a, b, c (Å) 5.3642 (3), 10.3773 (6), 12.1784 (7)
α, β, γ (°) 99.572 (5), 95.498 (5), 104.645 (5)
V (Å3) 639.98 (6)
Z 2
Radiation type Cu Kα
μ (mm−1) 2.14
Crystal size (mm) 0.30 × 0.10 × 0.03
 
Data collection
Diffractometer Oxford Diffraction Gemini S
Absorption correction Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.])
Tmin, Tmax 0.459, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections 5846, 2491, 2360
Rint 0.023
(sin θ/λ)max (Å−1) 0.620
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.121, 1.08
No. of reflections 2491
No. of parameters 186
No. of restraints 2
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.48, −0.36
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]), SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Supporting information

CCDC reference: 1403422

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2056989015010233/is5399sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015010233/is5399Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015010233/is5399Isup3.cml

checkCIF report


Chemical context top

Parasitic helminths possess a number of evolutionary strategies that facilitate their co-existence with their host and, as such, up to one third of the global population may suffer from helminthetic infections (de Silva et al., 2003). These parasites can secrete immunomodulatory molecules that prevent the parasites' clearance from the host without leaving the host vulnerable to opportunistic infections (Hewitson et al., 2009). ES-62 is one such immunomodulatory molecule, a protein, which was discovered in the secretions of the rodent filarial nematode Acanthocheilonema and demonstrated to induce an anti-inflammatory immunological phenotype (Harnett et al., 1989). ES-62 has been studied for its potential to treat human diseases relating to inflammation, for example collagen-induced arthritis or rheumatoid arthritis, and many positive outcomes have been demonstrated. A number of the significant anti-inflammatory activities of ES-62 are associated with post-translational glycosyl­ation and subsequent esterification by phospho­rylcholine. However, ES-62 is an immunogenic protein and is thus unsuitable as a drug itself (Harnett & Harnett, 2009). We have sought to capitalize on the immunomodulatory effects of ES-62 whilst avoiding its inherent undrugability through synthesizing a library of drug-like small molecules based upon phospho­rylcholine, the active moiety of ES-62. A series of sulfone analogues (Fig. 1) have proven to be of great significance in our investigations into collagen-induced arthritis. Despite the apparent simplicity of these molecules, we are aware of no relevant crystallographic study. As such, and as the title compound is of particular inter­est to our ongoing work (Al-Riyami et al., 2013), we report herein on the solid-state structure of the title compound.

Structural commentary top

The molecular structure of the title compound is shown in Fig. 2. The amine group is disordered over two equally occupied sites such that the lone pair of the pyramidal N atom is anti to O1 with respect to the plane defined by C1—S1—C9 for the conformer containing N1 but syn for the N1A conformer.

Supra­molecular features top

Neighbouring molecules related by translation along the a-axis direction are connected by two weak C—H···O hydrogen bonds involving O1 and C1 and C9/C9A (Table 1 and Fig. 3). This gives one-dimensional supra­molecular chains of molecules that propagate parallel to the crystallographic a-axis direction.

Other close inter­actions involve the disordered fragment. Thus the methyl group of C11A approaches the aromatic ring in a π geometry [closest contact C6···C11A = 3.345 (5) Å] whilst C11 forms unfeasibly short inter­molecular inter­actions with its centrosymmetrically related self – an inter­action that is relieved by the observed disorder.

Synthesis and crystallization top

A mixture of 2-[(4-methyl­benzyl)­sulfonyl]­ethyl methane­sulfonate and 1-methyl-4-[(vinyl­sulfonyl)­methyl]­benzene (4.880 g) was dissolved in di­chloro­methane (50 ml, dry) to which di­methyl­amine (4 ml, 2M in THF) was added at room temperature with stirring. The stirring was continued at room temperature overnight. The reaction mixture was extracted with a saturated solution of sodium carbonate. The organic layer was collected, dried over MgSO4, filtered and the solvents were removed under reduced pressure and the crude product was applied to a silica gel column chromatography using first ethyl acetate/n-hexane (1/1, RF = 0.1) and then ethyl acetate/methanol (9/1). The product was obtained as a white solid which was recrystallized from ethyl acetate/n-hexane (2.200 g) (m.p. 341–343 K). HRESIMS: calculated for C12H19NO2S, 241.1136; found: 241.1139.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. Models where the site occupancy factors of the disordered groups were allowed to refine gave occupancies equal to 50%. So in the final model, occupancies of all the disordered atoms were set to this value. The C9—C10 and C9A—C10A distances were restrained to be 1.53 (1) Å. All H atoms were placed in idealized positions and were refined in riding modes with C—H equal to 0.95, 0.98 and 0.99 Å for CH, CH2 and CH3 groups, respectively, and Uiso(H) = 1.5Ueq(C) for methyl groups and 1.2Ueq(C) for other groups.

Related literature top

For the immunomodulatory role of ES-62, see: de Silva et al. (2003); Harnett et al. (1989); Harnett & Harnett (2009); Hewitson et al. (2009). For sulfones and collagen-induced arthritis, see: Al-Riyami et al. (2013)

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. General structure of sulfone analogues. R represents alkyl chains and X represents halogen substituents.
[Figure 2] Fig. 2. The molecular structure of the title compound with non-H atoms shown as 50% probability ellipsoids. For the disordered fragment, the atoms labelled with the suffix `a' have been shown with hollow bonds whilst all other bonds are shown as solid lines.
[Figure 3] Fig. 3. Part of the molecular chain formed by translation along a highlighting the C—H···O contacts. Only one of the two disordered conformations is shown.
N,N-Dimethyl-2-[(4-methylbenzyl)sulfonyl]ethanamine top
Crystal data top
C12H19NO2SZ = 2
Mr = 241.34F(000) = 260
Triclinic, P1Dx = 1.252 Mg m−3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 5.3642 (3) ÅCell parameters from 3570 reflections
b = 10.3773 (6) Åθ = 5.2–72.9°
c = 12.1784 (7) ŵ = 2.14 mm−1
α = 99.572 (5)°T = 123 K
β = 95.498 (5)°Plate, colourless
γ = 104.645 (5)°0.30 × 0.10 × 0.03 mm
V = 639.98 (6) Å3
Data collection top
Oxford Diffraction Gemini S
diffractometer		2491 independent reflections
Radiation source: fine-focus sealed tube2360 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
ω scansθmax = 72.9°, θmin = 3.7°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		h = −4→6
Tmin = 0.459, Tmax = 0.938k = −12→11
5846 measured reflectionsl = −15→14
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0758P)2 + 0.2621P]
where P = (Fo2 + 2Fc2)/3
2491 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.48 e Å−3
2 restraintsΔρmin = −0.35 e Å−3
Crystal data top
C12H19NO2Sγ = 104.645 (5)°
Mr = 241.34V = 639.98 (6) Å3
Triclinic, P1Z = 2
a = 5.3642 (3) ÅCu Kα radiation
b = 10.3773 (6) ŵ = 2.14 mm−1
c = 12.1784 (7) ÅT = 123 K
α = 99.572 (5)°0.30 × 0.10 × 0.03 mm
β = 95.498 (5)°
Data collection top
Oxford Diffraction Gemini S
diffractometer		2491 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)		2360 reflections with I > 2σ(I)
Tmin = 0.459, Tmax = 0.938Rint = 0.023
5846 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0432 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.08Δρmax = 0.48 e Å−3
2491 reflectionsΔρmin = −0.35 e Å−3
186 parameters
Special details top

Experimental. 1H NMR (DMSO-d6): δ 7.28 (2H, d, J = 8.0 Hz), 7.21 (2H, d, J = 8.0 Hz), 4.44 (2H, s), 3.17 (2H, t, J = 14.3 Hz), 2.65 (2H, t, J = 14.3 Hz), 2.31 (3H, s), 2.16 (6H, s). 13C NMR (DMSO-d6): δ 137.7, 130.8, 129.0, 125.4, 58.4, 51.6, 49.0, 44.9, 20.7. IR (KBr): 1511, 1463, 1399, 1380, 1314, 1258, 1156, 1119, 1050, 892, 853, 822, 749 cm-1.

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
xyzUiso*/UeqOcc. (<1)
S10.89090 (7)0.52015 (4)0.66118 (3)0.02154 (16)
O11.1289 (2)0.48170 (12)0.68167 (11)0.0307 (3)
O20.9042 (2)0.63679 (12)0.60940 (10)0.0295 (3)
C10.6462 (3)0.38079 (16)0.57471 (13)0.0223 (3)
H1A0.47630.40210.57400.027*
H1B0.68660.37060.49660.027*
C20.6217 (3)0.24813 (16)0.61229 (13)0.0211 (3)
C30.7832 (3)0.16706 (17)0.57982 (14)0.0252 (4)
H30.91140.19610.53380.030*
C40.7579 (3)0.04422 (17)0.61421 (14)0.0259 (4)
H40.8692−0.01010.59120.031*
C50.5729 (3)−0.00109 (17)0.68174 (14)0.0262 (4)
C60.4119 (4)0.08042 (18)0.71320 (16)0.0300 (4)
H60.28380.05130.75920.036*
C70.4342 (3)0.20319 (17)0.67902 (14)0.0253 (4)
H70.32110.25680.70120.030*
C80.5437 (4)−0.13542 (19)0.71811 (18)0.0377 (5)
H8A0.5787−0.12010.80040.057*
H8B0.6676−0.18020.68560.057*
H8C0.3659−0.19330.69200.057*
C90.7696 (3)0.55043 (17)0.79112 (14)0.0248 (4)0.50
H9A0.58830.55620.77680.030*0.50
H9B0.76920.47410.83040.030*0.50
N10.8311 (7)0.7301 (3)0.9652 (3)0.0333 (7)0.50
C100.9410 (19)0.6837 (8)0.8655 (9)0.0264 (18)0.50
H10A1.11320.67110.89000.032*0.50
H10B0.96890.75540.82000.032*0.50
C110.9697 (14)0.8715 (5)1.0135 (4)0.0648 (15)0.50
H11A0.88220.90601.07430.097*0.50
H11B0.97070.92610.95510.097*0.50
H11C1.14920.87741.04350.097*0.50
C120.8399 (16)0.6456 (6)1.0475 (5)0.0683 (18)0.50
H12A0.74640.55121.01340.102*0.50
H12B0.75770.67701.11140.102*0.50
H12C1.02160.65131.07370.102*0.50
N1A0.9175 (6)0.6553 (3)0.9889 (3)0.0297 (7)0.50
C9A0.7696 (3)0.55043 (17)0.79112 (14)0.0248 (4)0.50
H9C0.61060.58130.77970.030*0.50
H9D0.72400.46540.82070.030*0.50
C10A0.9780 (18)0.6589 (8)0.8749 (8)0.0231 (17)0.50
H10C1.15040.64230.86880.028*0.50
H10D0.98480.74960.85780.028*0.50
C11A1.1294 (9)0.7511 (4)1.0688 (3)0.0394 (9)0.50
H11D1.29310.72841.05820.059*0.50
H11E1.09400.74611.14570.059*0.50
H11F1.14340.84341.05630.059*0.50
C12A0.6727 (9)0.6851 (5)1.0055 (4)0.0424 (10)0.50
H12D0.64510.68511.08390.064*0.50
H12E0.53010.61580.95540.064*0.50
H12F0.67720.77460.98840.064*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0207 (2)0.0219 (2)0.0214 (2)0.00508 (16)0.00401 (15)0.00319 (16)
O10.0228 (6)0.0307 (7)0.0357 (7)0.0074 (5)0.0033 (5)−0.0006 (5)
O20.0357 (7)0.0258 (6)0.0264 (6)0.0050 (5)0.0073 (5)0.0071 (5)
C10.0221 (8)0.0237 (8)0.0190 (7)0.0053 (6)0.0001 (6)0.0018 (6)
C20.0199 (7)0.0219 (8)0.0182 (7)0.0031 (6)−0.0027 (6)0.0016 (6)
C30.0220 (8)0.0285 (9)0.0240 (8)0.0066 (7)0.0043 (6)0.0018 (7)
C40.0231 (8)0.0255 (8)0.0267 (8)0.0084 (6)−0.0005 (6)−0.0011 (7)
C50.0261 (8)0.0231 (8)0.0258 (8)0.0039 (6)−0.0023 (6)0.0031 (6)
C60.0275 (9)0.0309 (9)0.0327 (9)0.0060 (7)0.0102 (7)0.0094 (7)
C70.0218 (8)0.0274 (8)0.0265 (8)0.0079 (7)0.0041 (6)0.0029 (7)
C80.0437 (11)0.0273 (9)0.0433 (11)0.0098 (8)0.0056 (9)0.0110 (8)
C90.0252 (8)0.0284 (8)0.0200 (8)0.0062 (7)0.0042 (6)0.0043 (6)
N10.045 (2)0.0337 (17)0.0244 (16)0.0202 (16)0.0042 (15)0.0002 (13)
C100.024 (3)0.034 (3)0.022 (3)0.013 (2)−0.0005 (19)0.001 (2)
C110.106 (5)0.042 (3)0.037 (2)0.017 (3)0.006 (3)−0.011 (2)
C120.121 (6)0.066 (4)0.033 (3)0.045 (4)0.025 (3)0.016 (3)
N1A0.0366 (17)0.0302 (17)0.0197 (17)0.0083 (14)−0.0003 (13)0.0013 (13)
C9A0.0252 (8)0.0284 (8)0.0200 (8)0.0062 (7)0.0042 (6)0.0043 (6)
C10A0.023 (3)0.027 (3)0.019 (2)0.009 (2)−0.0031 (18)0.003 (2)
C11A0.046 (2)0.040 (2)0.0253 (18)0.0098 (18)−0.0103 (16)−0.0028 (16)
C12A0.046 (2)0.053 (3)0.028 (2)0.020 (2)0.0083 (19)−0.0024 (18)
Geometric parameters (Å, º) top
S1—O11.4426 (13)C9—H9B0.9900
S1—O21.4446 (12)N1—C121.442 (6)
S1—C91.7780 (16)N1—C111.460 (6)
S1—C11.7867 (16)N1—C101.462 (12)
C1—C21.501 (2)C10—H10A0.9900
C1—H1A0.9900C10—H10B0.9900
C1—H1B0.9900C11—H11A0.9800
C2—C71.391 (2)C11—H11B0.9800
C2—C31.392 (2)C11—H11C0.9800
C3—C41.386 (2)C12—H12A0.9800
C3—H30.9500C12—H12B0.9800
C4—C51.390 (3)C12—H12C0.9800
C4—H40.9500N1A—C12A1.448 (6)
C5—C61.390 (2)N1A—C11A1.457 (5)
C5—C81.507 (2)N1A—C10A1.460 (12)
C6—C71.385 (2)C10A—H10C0.9900
C6—H60.9500C10A—H10D0.9900
C7—H70.9500C11A—H11D0.9800
C8—H8A0.9800C11A—H11E0.9800
C8—H8B0.9800C11A—H11F0.9800
C8—H8C0.9800C12A—H12D0.9800
C9—C101.536 (7)C12A—H12E0.9800
C9—H9A0.9900C12A—H12F0.9800
O1—S1—O2117.10 (8)H8B—C8—H8C109.5
O1—S1—C9108.51 (8)C10—C9—S1109.9 (5)
O2—S1—C9108.29 (8)C10—C9—H9A109.7
O1—S1—C1109.89 (7)S1—C9—H9A109.7
O2—S1—C1107.22 (7)C10—C9—H9B109.7
C9—S1—C1105.17 (8)S1—C9—H9B109.7
C2—C1—S1113.98 (11)H9A—C9—H9B108.2
C2—C1—H1A108.8C12—N1—C11110.8 (4)
S1—C1—H1A108.8C12—N1—C10111.7 (5)
C2—C1—H1B108.8C11—N1—C10109.5 (5)
S1—C1—H1B108.8N1—C10—C9113.9 (8)
H1A—C1—H1B107.7N1—C10—H10A108.8
C7—C2—C3118.87 (15)C9—C10—H10A108.8
C7—C2—C1120.38 (14)N1—C10—H10B108.8
C3—C2—C1120.74 (14)C9—C10—H10B108.8
C4—C3—C2120.35 (15)H10A—C10—H10B107.7
C4—C3—H3119.8C12A—N1A—C11A110.2 (3)
C2—C3—H3119.8C12A—N1A—C10A112.8 (4)
C3—C4—C5121.28 (15)C11A—N1A—C10A109.0 (4)
C3—C4—H4119.4N1A—C10A—H10C109.8
C5—C4—H4119.4N1A—C10A—H10D109.8
C4—C5—C6117.86 (16)H10C—C10A—H10D108.2
C4—C5—C8121.24 (16)N1A—C11A—H11D109.5
C6—C5—C8120.90 (16)N1A—C11A—H11E109.5
C7—C6—C5121.50 (16)H11D—C11A—H11E109.5
C7—C6—H6119.3N1A—C11A—H11F109.5
C5—C6—H6119.3H11D—C11A—H11F109.5
C6—C7—C2120.15 (15)H11E—C11A—H11F109.5
C6—C7—H7119.9N1A—C12A—H12D109.5
C2—C7—H7119.9N1A—C12A—H12E109.5
C5—C8—H8A109.5H12D—C12A—H12E109.5
C5—C8—H8B109.5N1A—C12A—H12F109.5
H8A—C8—H8B109.5H12D—C12A—H12F109.5
C5—C8—H8C109.5H12E—C12A—H12F109.5
H8A—C8—H8C109.5
O1—S1—C1—C247.30 (14)C8—C5—C6—C7−179.06 (16)
O2—S1—C1—C2175.57 (11)C5—C6—C7—C2−0.4 (3)
C9—S1—C1—C2−69.31 (13)C3—C2—C7—C60.7 (2)
S1—C1—C2—C796.45 (16)C1—C2—C7—C6179.81 (14)
S1—C1—C2—C3−84.47 (17)O1—S1—C9—C1072.2 (3)
C7—C2—C3—C4−0.4 (2)O2—S1—C9—C10−55.9 (3)
C1—C2—C3—C4−179.51 (14)C1—S1—C9—C10−170.2 (3)
C2—C3—C4—C5−0.2 (3)C12—N1—C10—C971.5 (7)
C3—C4—C5—C60.5 (3)C11—N1—C10—C9−165.3 (5)
C3—C4—C5—C8179.36 (16)S1—C9—C10—N1169.5 (4)
C4—C5—C6—C7−0.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O1i0.992.603.493 (2)150
C9—H9A···O1i0.992.493.415 (2)155
C9A—H9C···O1i0.992.613.415 (2)138
Symmetry code: (i) x−1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···O1i0.992.603.493 (2)150
C9—H9A···O1i0.992.493.415 (2)155
C9A—H9C···O1i0.992.613.415 (2)138
Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formulaC12H19NO2S
Mr241.34
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)5.3642 (3), 10.3773 (6), 12.1784 (7)
α, β, γ (°)99.572 (5), 95.498 (5), 104.645 (5)
V (Å3)639.98 (6)
Z2
Radiation typeCu Kα
µ (mm−1)2.14
Crystal size (mm)0.30 × 0.10 × 0.03
Data collection
DiffractometerOxford Diffraction Gemini S
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.459, 0.938
No. of measured, independent and
observed [I > 2σ(I)] reflections		5846, 2491, 2360
Rint0.023
(sin θ/λ)max (Å−1)0.620
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.121, 1.08
No. of reflections2491
No. of parameters186
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.48, −0.35

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008).

 

References

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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSilva, N. R. de, Brooker, S., Hotez, P. J., Montresor, A., Engels, D. & Savioli, L. (2003). Trends Parasitol. 19, 547–551.  Web of Science PubMed Google Scholar

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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages 757-759
doi:10.1107/S2056989015010233
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