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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3350
https://doi.org/10.1107/S1600536811047027

Ethyl 2-[N-(tert-butyl­sulfin­yl)carbamo­yl]benzoate

Aurelien Honraedt,a,b Sonia Ladeira,a,b Thierry Berrangerc and Emmanuel Grasa,b*

aCNRS, LCC, 205 route de Narbonne, F-31077 Toulouse, France, bUniversité de Toulouse, UPS, INPT, LCC, F31077 Toulouse, France, and cMinakem, 145 Chemin des Lilas, F-59310 Beuvry-La-Foret, France
*Correspondence e-mail: emmanuel.gras@lcc-toulouse.fr

(Received 19 October 2011; accepted 7 November 2011; online 19 November 2011)

The title compound, C14H19NO4S, was obtained in quanti­tative yield by Lewis acid-catalysed alcoholysis of a phtalimide precursor. An intra­molecular C—H⋯O hydrogen bond occurs. In the crystal, centrosymmetric dimers are formed by pairs of N—H⋯O hydrogen bonds between the sulfinyl O atoms and the carbamoyl N—H group of a neighboring mol­ecule. C—H⋯O inter­actions feature in the crystal structure.

Related literature

For a related compound, see: Harpp & Back (1973[Harpp, D. N. & Back, T. G. (1973). J. Org. Chem. 38, 4328-4334.]). For hydrogen-bond motifs and graph-set notation, see: Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]); Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For potential applications of the title compound in the synthesis of enones, see: Wang et al. (2005[Wang, W., Mei, Y., Li, H. & Wang, J. (2005). Org. Lett. 7, 601-604.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C14H19NO4S

  • Mr = 297.37

  • Monoclinic, P 21 /c

  • a = 11.7881 (3) Å

  • b = 9.0056 (2) Å

  • c = 16.3296 (4) Å

  • β = 120.091 (2)°

  • V = 1499.91 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.23 mm−1

  • T = 180 K

  • 0.4 × 0.25 × 0.03 mm
Data collection

  • Oxford-Diffraction Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.930, Tmax = 0.990

  • 15187 measured reflections

  • 2744 independent reflections

  • 2334 reflections with I > 2s(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.029

  • wR(F2) = 0.088

  • S = 1.12

  • 2744 reflections

  • 188 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H101⋯O4i 0.86 (1) 2.00 (1) 2.857 (2) 173 (2)
C5—H5⋯O2ii 0.95 2.59 3.469 (3) 155
C13—H13C⋯O2 0.98 2.37 3.345 (2) 174
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: 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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: 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.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811047027/im2332sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811047027/im2332Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811047027/im2332Isup3.cml

checkCIF report


Comment top

In the course of our studies on tert-butylsulfinyl phtalimide we have uncovered an unusual access to ethyl 2-(tert-butylsulfinylcarbamoyl)benzoate (I) based on the Lewis acid activation (for example by Samarium (III) salts) of one C=O bond of the phtalimide moiety. The title compound has been obtained quantitative yield.

Interestingly (I) exhibits one hydrogen donor (NH) and 5 electronegative atoms featuring available lone pairs that therefore should be able to act as hydrogen acceptors (4 oxygen and one sulfur). The combination of these donors and acceptors can induce a wide variety of hydrogen-bond patterns. A preferred one can be indicative of higher H-bond acceptor ability of one group.

Moreover, these features are of interest for potential applications in organocatalysis. Indeed acidic imide hydrogen atoms have been shown to favour organocatalytic processes in the formation of enones under mild reaction conditions. (Wang et al. 2005)

The crystal structure clearly establishes N–H···O contacts between the O atoms of the sulfinyl groups and the NH groups since the N···O distance falls by more than 0.2Å below he sum of the van-der-Waals radii of the atoms involved. This is strongly indicative of the presence of two intermolecular hydrogen bonds. From that point, a cyclic dimer is observed with a R22(8) graph set (Fig. 2). Interestingly although isographic to the sulfinyl group (i.e. it has the same graph set but is chemically different), the carbonyl group of the amide is not involved in any hydrogen bond. This is a clear illustration of the higher polar character of the S=O bond making the sulfinyl oxygen a better H-bond acceptor than its carbonyl counterpart.

The R22(8) graph set is a six bonds ring system exhibiting a chair like conformation in which the two tert-butyl groups are in axial positions and the two carbamoyl units in equatorial positions (Fig. 2). An unexpectedly small distance (in the range of the sum of the van-der-Waals radii) is observed between the oxygen of the carboxyl group of the ester and the nitrogen. The observed conformation might be minimizing the repulsive coulombic interaction and steric repulsions. All bond lengths and angles are otherwise normal. (Allen et al. 1987) Finally as the reaction has been carried out on racemic tert-butylsulfinyl phtalimide, (I) has been obtained as a racemate. It can be seen from the crystal structure that (I) crystallizes as a racemic compound (i.e. the two enantiomers forming dimers in the crystal lattice) indicating that no spontaneous resolution happens (formation of conglomerates).

Related literature top

For a related compound, see: Harpp & Back (1973). For hydrogen-bond motifs and graph-set notation, see: Etter (1990); Bernstein et al. (1995). For potential applications of the title compound in the synthesis of enones, see: Wang et al. (2005).

For related literature, see: Allen et al. (1987).

Experimental top

To a suspension of 100 mg (0.398 mmol) of tert-butylsulfinyl phtalimide in 5 ml of ethanol stirred at room temperature is added a solution of 24 mg (0.04 mmol) of samarium(III) trifluoromethanesulfonate in 5 ml of ethanol. After 0.5 h of stirring at room temperature a complete solubilization is observed and a full conversion is confirmed by TLC (cyclohexane/diethyl ether: 2/8). After concentration of the reaction mixture under reduced pressure, the remainings are diluted with 10 ml of dichloromethane and washed twice with water (2x5 ml). The aqueous phases are extracted twice with 10 ml of dichloromethane. The combined organic phases are dried of sodium sulfate and concentrated to dryness under reduced pressure to give 118.1 mg (100% yield) of a white solid. Crystals of (I) suitable for X-ray diffraction were grown overnight at -20 °C in a 95/5 Diethyl ether/dichloromethane mixture.

Refinement top

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.98 Å (methyl) or 0.95 Å (aromatic) or 0.97 Å (methylene) with Uiso(H) = 1.2Ueq(C). The H attached to nitrogen has been located on difference Fourier and its coordinates were refined using N—H restraints of 0.88 (1) Å with Uiso(H) = 1.2Ueq(N).

Structure description top

In the course of our studies on tert-butylsulfinyl phtalimide we have uncovered an unusual access to ethyl 2-(tert-butylsulfinylcarbamoyl)benzoate (I) based on the Lewis acid activation (for example by Samarium (III) salts) of one C=O bond of the phtalimide moiety. The title compound has been obtained quantitative yield.

Interestingly (I) exhibits one hydrogen donor (NH) and 5 electronegative atoms featuring available lone pairs that therefore should be able to act as hydrogen acceptors (4 oxygen and one sulfur). The combination of these donors and acceptors can induce a wide variety of hydrogen-bond patterns. A preferred one can be indicative of higher H-bond acceptor ability of one group.

Moreover, these features are of interest for potential applications in organocatalysis. Indeed acidic imide hydrogen atoms have been shown to favour organocatalytic processes in the formation of enones under mild reaction conditions. (Wang et al. 2005)

The crystal structure clearly establishes N–H···O contacts between the O atoms of the sulfinyl groups and the NH groups since the N···O distance falls by more than 0.2Å below he sum of the van-der-Waals radii of the atoms involved. This is strongly indicative of the presence of two intermolecular hydrogen bonds. From that point, a cyclic dimer is observed with a R22(8) graph set (Fig. 2). Interestingly although isographic to the sulfinyl group (i.e. it has the same graph set but is chemically different), the carbonyl group of the amide is not involved in any hydrogen bond. This is a clear illustration of the higher polar character of the S=O bond making the sulfinyl oxygen a better H-bond acceptor than its carbonyl counterpart.

The R22(8) graph set is a six bonds ring system exhibiting a chair like conformation in which the two tert-butyl groups are in axial positions and the two carbamoyl units in equatorial positions (Fig. 2). An unexpectedly small distance (in the range of the sum of the van-der-Waals radii) is observed between the oxygen of the carboxyl group of the ester and the nitrogen. The observed conformation might be minimizing the repulsive coulombic interaction and steric repulsions. All bond lengths and angles are otherwise normal. (Allen et al. 1987) Finally as the reaction has been carried out on racemic tert-butylsulfinyl phtalimide, (I) has been obtained as a racemate. It can be seen from the crystal structure that (I) crystallizes as a racemic compound (i.e. the two enantiomers forming dimers in the crystal lattice) indicating that no spontaneous resolution happens (formation of conglomerates).

For a related compound, see: Harpp & Back (1973). For hydrogen-bond motifs and graph-set notation, see: Etter (1990); Bernstein et al. (1995). For potential applications of the title compound in the synthesis of enones, see: Wang et al. (2005).

For related literature, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. ORTEP representation of (I) (Mercury; Macrae et al., 2008) with ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Dimeric structure showing the pair of intermolecular H–bonds and the chair like conformation of the core of the dimer with the two tert-butyl groups in axial positions. Only hydrogens involved in the H–bonds are represented; others were omitted for clarity.
Ethyl 2-[N-(tert-butylsulfinyl)carbamoyl]benzoate top
Crystal data top
C14H19NO4SF(000) = 632
Mr = 297.37Dx = 1.317 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9878 reflections
a = 11.7881 (3) Åθ = 2.9–29.0°
b = 9.0056 (2) ŵ = 0.23 mm−1
c = 16.3296 (4) ÅT = 180 K
β = 120.091 (2)°Block, colourless
V = 1499.91 (7) Å30.4 × 0.25 × 0.03 mm
Z = 4
Data collection top
Oxford-Diffraction Gemini
diffractometer		2744 independent reflections
Radiation source: Enhance (Mo) X-ray Source2334 reflections with I > 2s(I)
Graphite monochromatorRint = 0.022
ω scanθmax = 25.4°, θmin = 2.9°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		h = −14→14
Tmin = 0.930, Tmax = 0.990k = −10→10
15187 measured reflectionsl = −19→18
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0508P)2 + 0.2576P]
where P = (Fo2 + 2Fc2)/3
2744 reflections(Δ/σ)max < 0.001
188 parametersΔρmax = 0.50 e Å−3
1 restraintΔρmin = −0.28 e Å−3
Crystal data top
C14H19NO4SV = 1499.91 (7) Å3
Mr = 297.37Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.7881 (3) ŵ = 0.23 mm−1
b = 9.0056 (2) ÅT = 180 K
c = 16.3296 (4) Å0.4 × 0.25 × 0.03 mm
β = 120.091 (2)°
Data collection top
Oxford-Diffraction Gemini
diffractometer		2744 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)		2334 reflections with I > 2s(I)
Tmin = 0.930, Tmax = 0.990Rint = 0.022
15187 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0291 restraint
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.50 e Å−3
2744 reflectionsΔρmin = −0.28 e Å−3
188 parameters
Special details top

Experimental. 1H NMR (CDCl3, 400?MHz): 8.01 (s, 1H); 7.61–7.55 (m, 4H); 4.40 (q, J 7.2?Hz, 2H); 1.40 (t, J 7.2?Hz, 3H); 1.33 (s, 9H). 13C NMR (CDCl3, 100.6?MHz, T= 233?K): 171.8; 165.6; 136.1; 132.5; 130.5; 130.1; 129.1; 127.6; 62.0; 57.8; 22.4; 14.0. MS (DCI, NH3): 315.0; IR (cm-1): 3068; 2971; 1710; 1688; 1428; 1247; 1062; 885;805; 703. MP: 129–131 °C.

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
xyzUiso*/Ueq
C10.9715 (2)0.8337 (3)0.54534 (15)0.0587 (6)
H1A0.88120.84630.49340.088*
H1B1.02810.80810.51950.088*
H1C1.00210.92650.58130.088*
C20.97629 (19)0.7127 (2)0.60890 (14)0.0419 (4)
H2A0.94510.61840.57330.05*
H2B1.06730.69820.66140.05*
C30.87361 (14)0.65483 (17)0.69751 (10)0.0262 (3)
C40.79014 (14)0.71356 (17)0.73504 (10)0.0241 (3)
C50.79902 (17)0.86253 (18)0.76008 (12)0.0328 (4)
H50.85540.92690.75070.039*
C60.72634 (19)0.9176 (2)0.79856 (13)0.0409 (4)
H60.73171.01970.81460.049*
C70.64604 (18)0.8236 (2)0.81356 (12)0.0386 (4)
H70.59650.86110.84030.046*
C80.63737 (16)0.67464 (19)0.78977 (11)0.0296 (4)
H80.58220.61060.80060.036*
C90.70872 (14)0.61845 (16)0.75018 (10)0.0224 (3)
C100.68801 (14)0.45713 (16)0.72159 (10)0.0224 (3)
C110.68034 (15)0.22686 (16)0.52516 (10)0.0255 (3)
C120.67874 (18)0.35133 (19)0.46180 (12)0.0344 (4)
H12A0.72990.32160.43220.052*
H12B0.71720.4410.49980.052*
H12C0.58810.37170.41250.052*
C130.81679 (16)0.20074 (19)0.60975 (12)0.0350 (4)
H13A0.87550.16650.58750.052*
H13B0.81210.12530.65120.052*
H13C0.85050.29370.6450.052*
C140.62431 (19)0.08368 (19)0.46900 (13)0.0410 (4)
H14A0.53370.10070.41860.062*
H14B0.62610.00550.51140.062*
H14C0.67720.0530.4410.062*
N10.63756 (12)0.43515 (13)0.62653 (8)0.0215 (3)
H1010.6177 (16)0.5099 (14)0.5890 (10)0.026*
O10.89198 (11)0.75638 (12)0.64578 (8)0.0332 (3)
O20.92023 (11)0.53207 (12)0.71343 (9)0.0365 (3)
O30.70681 (12)0.35692 (12)0.77681 (7)0.0352 (3)
O40.44238 (10)0.30802 (11)0.49210 (7)0.0278 (3)
S10.57360 (4)0.27051 (4)0.57391 (2)0.02149 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0548 (13)0.0834 (16)0.0556 (12)0.0132 (12)0.0408 (11)0.0184 (12)
C20.0404 (10)0.0503 (11)0.0517 (11)0.0016 (8)0.0355 (9)−0.0005 (9)
C30.0211 (8)0.0294 (9)0.0285 (8)−0.0069 (6)0.0128 (6)−0.0054 (6)
C40.0244 (8)0.0265 (8)0.0219 (7)−0.0029 (6)0.0119 (6)−0.0028 (6)
C50.0379 (9)0.0297 (9)0.0376 (9)−0.0096 (7)0.0239 (8)−0.0078 (7)
C60.0533 (12)0.0303 (9)0.0514 (11)−0.0087 (8)0.0353 (10)−0.0161 (8)
C70.0458 (11)0.0393 (10)0.0439 (10)−0.0035 (8)0.0325 (9)−0.0124 (8)
C80.0317 (9)0.0352 (9)0.0277 (8)−0.0055 (7)0.0192 (7)−0.0033 (7)
C90.0215 (7)0.0265 (8)0.0162 (7)−0.0014 (6)0.0073 (6)−0.0015 (6)
C100.0196 (7)0.0265 (8)0.0226 (7)−0.0011 (6)0.0116 (6)0.0008 (6)
C110.0301 (8)0.0229 (8)0.0280 (8)0.0013 (6)0.0180 (7)−0.0009 (6)
C120.0413 (10)0.0367 (10)0.0358 (9)0.0056 (7)0.0272 (8)0.0076 (7)
C130.0321 (9)0.0341 (9)0.0390 (9)0.0102 (7)0.0180 (8)0.0038 (7)
C140.0496 (11)0.0339 (9)0.0465 (10)−0.0044 (8)0.0294 (9)−0.0145 (8)
N10.0263 (7)0.0169 (6)0.0204 (6)−0.0014 (5)0.0111 (5)0.0015 (5)
O10.0352 (7)0.0354 (6)0.0407 (6)0.0007 (5)0.0276 (6)0.0012 (5)
O20.0307 (6)0.0293 (6)0.0570 (8)0.0010 (5)0.0275 (6)−0.0006 (5)
O30.0486 (7)0.0286 (6)0.0267 (6)−0.0010 (5)0.0177 (5)0.0059 (5)
O40.0244 (6)0.0241 (5)0.0290 (6)−0.0026 (4)0.0090 (5)−0.0013 (4)
S10.0251 (2)0.01767 (19)0.0227 (2)−0.00142 (13)0.01277 (16)0.00053 (13)
Geometric parameters (Å, º) top
C1—C21.486 (3)C9—C101.508 (2)
C1—H1A0.98C10—O31.2150 (18)
C1—H1B0.98C10—N11.3699 (19)
C1—H1C0.98C11—C121.519 (2)
C2—O11.451 (2)C11—C131.524 (2)
C2—H2A0.99C11—C141.527 (2)
C2—H2B0.99C11—S11.8373 (16)
C3—O21.2036 (19)C12—H12A0.98
C3—O11.3343 (19)C12—H12B0.98
C3—C41.493 (2)C12—H12C0.98
C4—C51.391 (2)C13—H13A0.98
C4—C91.398 (2)C13—H13B0.98
C5—C61.384 (2)C13—H13C0.98
C5—H50.95C14—H14A0.98
C6—C71.380 (3)C14—H14B0.98
C6—H60.95C14—H14C0.98
C7—C81.386 (2)N1—S11.6898 (12)
C7—H70.95N1—H1010.860 (9)
C8—C91.388 (2)O4—S11.4898 (11)
C8—H80.95
C2—C1—H1A109.5O3—C10—C9123.02 (13)
C2—C1—H1B109.5N1—C10—C9113.63 (12)
H1A—C1—H1B109.5C12—C11—C13112.22 (14)
C2—C1—H1C109.5C12—C11—C14111.10 (13)
H1A—C1—H1C109.5C13—C11—C14110.86 (14)
H1B—C1—H1C109.5C12—C11—S1111.09 (11)
O1—C2—C1107.28 (15)C13—C11—S1106.33 (10)
O1—C2—H2A110.3C14—C11—S1104.89 (11)
C1—C2—H2A110.3C11—C12—H12A109.5
O1—C2—H2B110.3C11—C12—H12B109.5
C1—C2—H2B110.3H12A—C12—H12B109.5
H2A—C2—H2B108.5C11—C12—H12C109.5
O2—C3—O1124.39 (15)H12A—C12—H12C109.5
O2—C3—C4124.08 (14)H12B—C12—H12C109.5
O1—C3—C4111.52 (13)C11—C13—H13A109.5
C5—C4—C9119.75 (14)C11—C13—H13B109.5
C5—C4—C3119.63 (14)H13A—C13—H13B109.5
C9—C4—C3120.52 (13)C11—C13—H13C109.5
C6—C5—C4120.43 (15)H13A—C13—H13C109.5
C6—C5—H5119.8H13B—C13—H13C109.5
C4—C5—H5119.8C11—C14—H14A109.5
C7—C6—C5119.79 (16)C11—C14—H14B109.5
C7—C6—H6120.1H14A—C14—H14B109.5
C5—C6—H6120.1C11—C14—H14C109.5
C6—C7—C8120.32 (16)H14A—C14—H14C109.5
C6—C7—H7119.8H14B—C14—H14C109.5
C8—C7—H7119.8C10—N1—S1122.17 (10)
C7—C8—C9120.43 (15)C10—N1—H101120.2 (11)
C7—C8—H8119.8S1—N1—H101115.6 (11)
C9—C8—H8119.8C3—O1—C2116.06 (13)
C8—C9—C4119.29 (14)O4—S1—N1104.78 (6)
C8—C9—C10116.97 (14)O4—S1—C11106.78 (7)
C4—C9—C10123.68 (13)N1—S1—C11100.38 (7)
O3—C10—N1123.21 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···O4i0.86 (1)2.00 (1)2.857 (2)173 (2)
C5—H5···O2ii0.952.593.469 (3)155
C13—H13C···O20.982.373.345 (2)174
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC14H19NO4S
Mr297.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)180
a, b, c (Å)11.7881 (3), 9.0056 (2), 16.3296 (4)
β (°) 120.091 (2)
V (Å3)1499.91 (7)
Z4
Radiation typeMo Kα
µ (mm−1)0.23
Crystal size (mm)0.4 × 0.25 × 0.03
Data collection
DiffractometerOxford-Diffraction Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.930, 0.990
No. of measured, independent and
observed [I > 2s(I)] reflections		15187, 2744, 2334
Rint0.022
(sin θ/λ)max (Å−1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.088, 1.12
No. of reflections2744
No. of parameters188
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.50, −0.28

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H101···O4i0.86 (1)2.00 (1)2.857 (2)173 (2)
C5—H5···O2ii0.95002.59003.469 (3)155.00
C13—H13C···O20.98002.37003.345 (2)174.00
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2.
 

Acknowledgements

Minakem is acknowledged for PhD funding (for AH). Dr J.-C. Daran is warmly acknowledged for his kind help during the preparation of this paper.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
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 First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3350
https://doi.org/10.1107/S1600536811047027
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