N-(3-Methoxy­phen­yl)-tert-butane­sulfinamide

Datta, M.; Buglass, A.J.; Elsegood, M.R.J.

doi:10.1107/S1600536809052507

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o109

doi:10.1107/S1600536809052507

Open

access

N-(3-Methoxyphenyl)-tert-butanesulfinamide

Mrityunjoy Datta,^a Alan J. Buglass ^a ^* and Mark R. J. Elsegood ^b

^aDepartment of Chemistry, KAIST, Daejeon 305-701, Republic of Korea, and ^bChemistry Department, Loughborough University, Loughborough LE11 3TU, England
^*Correspondence e-mail: ajbuglass@kaist.ac.kr

(Received 27 November 2009; accepted 7 December 2009; online 12 December 2009)

In the title compound, C₁₁H₁₇NO₂S, the molecules interact in a head-to-tail fashion through pairs of N—H⋯O hydrogen bonds, giving discrete centrosymmetric dimers. The N(H)S(O)^tBu fragment is disordered over two sets of positions, with the major component comprising 90.0 (2)%.

Related literature

For N-arylalkanesulfinamides, see: Datta et al. (2008 , 2009 ). For N-alkylalkanesulfinamides, see: Sato et al. (1975 ); Ferreira et al. (2005 ); Schuckmann et al. (1978 ). For the synthesis, see: Stretter et al. (1969 ).

Experimental

Crystal data

C₁₁H₁₇NO₂S
M_r = 227.32
Monoclinic, P 2₁ /n
a = 12.4068 (13) Å
b = 7.3076 (8) Å
c = 12.9230 (13) Å
β = 93.2992 (15)°
V = 1169.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 150 K
0.37 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.911, T_max = 0.950
10627 measured reflections
2633 independent reflections
2237 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.07
2633 reflections
166 parameters
149 restraints
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.24	2.884 (2)	130
N1X—H1X⋯O1Xⁱⁱ	0.88	2.21	2.94 (2)	141
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052507/ng2698sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052507/ng2698Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound (I) exhibits disorder of the N(H)S(O)^tBu fragment over two sets of positions. The major component comprises 90.0 (2)% (Fig. 1), in which the N—C_arylbond length is 1.418 (2) Å, similar to that [1.4225 (14) Å] in N-(4-methoxyphenyl)-tert-butanesulfinamide (Datta et al., 2009). The corresponding bond length [1.457 (16) Å] in the minor component is longer, though far less precisely determined. This perhaps suggests weaker delocalization of electrons over N and the aromatic ring, which would correlate with the greater non-coplanarity of the aromatic ring and sulfinyl moiety in this component. In either case, however, the N—C_arylbond is shorter than the N—C_alkyl bonds [1.470–1.530 Å] observed in structures of N-alkylalkanesulfinamides (Sato et al., 1975; Schuckmann et al., 1978; Ferreira et al., 2005). The crystal packing of (I) shows head-to-tail interaction through NH···OS hydrogen bonds, forming discrete centrosymmetric dimers, as illustrated for the major component in Fig. 2. The hydrogen bonding data for both components are listed in Table 1. There is no evidence of hydrogen bonding involving the methoxy group, nor of weak CH···.OS hydrogen bonding, as observed in the packing of N-phenyladamantane-1-sulfinamide (Datta et al., 2008).

Related literature top

For N-arylalkanesulfinamides, see: Datta et al. (2008, 2009). For N-alkylalkanesulfinamides, see: Sato et al. (1975); Ferreira et al. (2005); Schuckmann et al. (1978). For the synthesis, see: Stretter et al. (1969).

Experimental top

Compound (I) was prepared by the method of Stretter et al. (1969), using tert-butanesulfinyl chloride (281 mg, 2 mmol) and 3-methoxyaniline (492 mg, 4 mmol) in dry ether (20 ml). After 5 h (with TLC monitoring) the colourless solid amine salt was fitered off and the solvent was removed under reduced pressure. Column chromatography (silica gel, 1% methanol-dichloromethane) provided (I) as colourless crystals (430 mg, 95%), m.p. 367 K. Single crystals suitable for X-ray analysis were obtained by evaporation of a solution of (I) in dichloromethane:hexane (1:1) at room temperature. Spectroscopic analysis: FTIR (KBr) (cm^-1) 3024, 1603, 1496, 1473, 1368, 1278, 1227, 1214, 1156, 1069, 953, 834. ¹H NMR (400 MHz, CDCl₃ p.p.m. with respect to TMS) δ 7.13 (dd, J = 8.0, 8.5 Hz, 1H), 6.58–6.53 (m, 3H), 5.41 (bs, 1H), 3.75 (d, J = 0.6 Hz, 3H), 1.30 (s, 9H). ¹³C (100 MHz, CDCl₃ p.p.m. with respect to TMS) δ 160.6, 143.3, 130.2, 110.6, 108.4, 104.2, 56.4. 55.2. 22.4. EIMS m/z (%) 228 (MH⁺, 85), 227 (M⁺, 25), 213 (17), 171 (MH⁺ - tBu, 100), 123 (MH⁺ - ^tBuSO, 6), 108 (MH⁺ - ^tBuSONH, 12), 95 (53). To our knowledge, these are the first reported analytical data for (I).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. Molecular structure of the major component of (I) with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Centrosymmetric dimer of (I) in the crystal packing of the major component, showing intermolecular hydrogen bonding. Symmetry code i = -x + 1, -y, -z + 1.

N-(3-Methoxyphenyl)-tert-butanesulfinamide top

Crystal data top

C₁₁H₁₇NO₂S	F(000) = 488
M_r = 227.32	D_x = 1.291 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4390 reflections
a = 12.4068 (13) Å	θ = 2.2–27.2°
b = 7.3076 (8) Å	µ = 0.26 mm⁻¹
c = 12.9230 (13) Å	T = 150 K
β = 93.2992 (15)°	Block, colourless
V = 1169.7 (2) Å³	0.37 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2633 independent reflections
Radiation source: fine-focus sealed tube	2237 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ω rotation with narrow frames scans	θ_max = 27.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −15→16
T_min = 0.911, T_max = 0.950	k = −9→9
10627 measured reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.056P)² + 0.7085P] where P = (F_o² + 2F_c²)/3
2633 reflections	(Δ/σ)_max = 0.001
166 parameters	Δρ_max = 0.62 e Å⁻³
149 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₁H₁₇NO₂S	V = 1169.7 (2) Å³
M_r = 227.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.4068 (13) Å	µ = 0.26 mm⁻¹
b = 7.3076 (8) Å	T = 150 K
c = 12.9230 (13) Å	0.37 × 0.22 × 0.20 mm
β = 93.2992 (15)°

Data collection top

Bruker APEXII CCD diffractometer	2633 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	2237 reflections with I > 2σ(I)
T_min = 0.911, T_max = 0.950	R_int = 0.032
10627 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	149 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.07	Δρ_max = 0.62 e Å⁻³
2633 reflections	Δρ_min = −0.40 e Å⁻³
166 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	Occ. (<1)
O1	0.54940 (10)	−0.05258 (18)	0.36978 (10)	0.0229 (3)	0.900 (2)
S1	0.50816 (3)	0.13248 (6)	0.33748 (3)	0.01938 (15)	0.900 (2)
N1	0.42312 (12)	0.2035 (3)	0.42415 (12)	0.0236 (4)	0.900 (2)
H1	0.4482	0.2281	0.4877	0.028*	0.900 (2)
C1	0.31128 (13)	0.2253 (2)	0.39789 (13)	0.0253 (4)
C2	0.24035 (14)	0.2103 (3)	0.47687 (14)	0.0277 (4)
H2	0.2669	0.1811	0.5453	0.033*
C3	0.13034 (14)	0.2383 (3)	0.45550 (14)	0.0289 (4)
O2	0.06872 (11)	0.2258 (3)	0.54029 (11)	0.0462 (4)
C11	−0.04594 (16)	0.2441 (4)	0.52212 (19)	0.0487 (6)
H11A	−0.0626	0.3643	0.4916	0.073*
H11B	−0.0808	0.2325	0.5879	0.073*
H11C	−0.0727	0.1480	0.4744	0.073*
C4	0.08935 (14)	0.2716 (3)	0.35566 (15)	0.0300 (4)
H4	0.0140	0.2867	0.3407	0.036*
C5	0.16122 (16)	0.2821 (3)	0.27816 (15)	0.0384 (5)
H5	0.1340	0.3040	0.2090	0.046*
C6	0.27117 (15)	0.2620 (3)	0.29758 (14)	0.0328 (4)
H6	0.3188	0.2731	0.2429	0.039*
C7	0.62017 (14)	0.2928 (3)	0.36663 (14)	0.0212 (4)	0.900 (2)
C8	0.57870 (17)	0.4793 (3)	0.32914 (18)	0.0314 (5)	0.900 (2)
H8A	0.5209	0.5198	0.3724	0.047*	0.900 (2)
H8B	0.5507	0.4698	0.2569	0.047*	0.900 (2)
H8C	0.6379	0.5682	0.3341	0.047*	0.900 (2)
C9	0.65533 (15)	0.2918 (3)	0.48138 (15)	0.0262 (4)	0.900 (2)
H9A	0.6810	0.1694	0.5015	0.039*	0.900 (2)
H9B	0.5939	0.3248	0.5220	0.039*	0.900 (2)
H9C	0.7137	0.3807	0.4945	0.039*	0.900 (2)
C10	0.7108 (2)	0.2247 (6)	0.3005 (2)	0.0282 (7)	0.900 (2)
H10A	0.7359	0.1048	0.3258	0.042*	0.900 (2)
H10B	0.7710	0.3118	0.3054	0.042*	0.900 (2)
H10C	0.6835	0.2141	0.2281	0.042*	0.900 (2)
O1X	0.5509 (11)	0.5520 (16)	0.3695 (10)	0.032 (3)*	0.100 (2)
S1X	0.5084 (4)	0.3681 (6)	0.3374 (3)	0.0303 (15)*	0.100 (2)
N1X	0.4214 (12)	0.288 (2)	0.4216 (13)	0.026 (4)*	0.100 (2)
H1X	0.4450	0.2833	0.4871	0.032*	0.100 (2)
C7X	0.6173 (12)	0.204 (2)	0.3663 (12)	0.029 (4)*	0.100 (2)
C8X	0.5762 (16)	0.016 (2)	0.3308 (16)	0.034 (4)*	0.100 (2)
H8D	0.5135	−0.0179	0.3694	0.052*	0.100 (2)
H8E	0.6335	−0.0751	0.3436	0.052*	0.100 (2)
H8F	0.5553	0.0197	0.2565	0.052*	0.100 (2)
C9X	0.6514 (16)	0.199 (3)	0.4840 (12)	0.032 (5)*	0.100 (2)
H9D	0.6766	0.3204	0.5065	0.048*	0.100 (2)
H9E	0.7096	0.1097	0.4964	0.048*	0.100 (2)
H9F	0.5893	0.1635	0.5231	0.048*	0.100 (2)
C10X	0.7138 (19)	0.269 (4)	0.308 (2)	0.025 (8)*	0.100 (2)
H10D	0.7374	0.3893	0.3344	0.038*	0.100 (2)
H10E	0.6927	0.2793	0.2338	0.038*	0.100 (2)
H10F	0.7731	0.1813	0.3179	0.038*	0.100 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0234 (6)	0.0218 (7)	0.0233 (6)	0.0001 (5)	0.0005 (5)	0.0005 (5)
S1	0.0152 (2)	0.0251 (2)	0.0179 (2)	0.00068 (16)	0.00179 (14)	0.00043 (17)
N1	0.0151 (8)	0.0366 (11)	0.0193 (8)	0.0024 (7)	0.0019 (6)	0.0015 (7)
C1	0.0168 (8)	0.0337 (10)	0.0254 (9)	0.0007 (6)	0.0014 (6)	0.0012 (7)
C2	0.0215 (9)	0.0385 (10)	0.0230 (8)	−0.0003 (7)	0.0009 (6)	0.0003 (7)
C3	0.0189 (8)	0.0400 (10)	0.0282 (9)	0.0001 (7)	0.0047 (7)	−0.0026 (7)
O2	0.0164 (7)	0.0900 (13)	0.0327 (8)	0.0034 (7)	0.0060 (5)	0.0010 (7)
C11	0.0156 (9)	0.0850 (19)	0.0464 (12)	0.0009 (10)	0.0083 (8)	−0.0025 (12)
C4	0.0180 (8)	0.0380 (10)	0.0336 (10)	0.0047 (7)	−0.0021 (7)	−0.0017 (8)
C5	0.0284 (10)	0.0603 (14)	0.0259 (9)	0.0128 (9)	−0.0022 (7)	0.0034 (9)
C6	0.0243 (9)	0.0504 (12)	0.0241 (9)	0.0076 (8)	0.0050 (7)	0.0068 (8)
C7	0.0165 (8)	0.0226 (10)	0.0251 (9)	−0.0010 (7)	0.0064 (6)	−0.0021 (8)
C8	0.0282 (10)	0.0240 (10)	0.0431 (12)	0.0031 (8)	0.0109 (9)	0.0028 (9)
C9	0.0187 (9)	0.0324 (12)	0.0277 (10)	−0.0042 (8)	0.0026 (7)	−0.0061 (8)
C10	0.0195 (12)	0.0340 (18)	0.0321 (14)	0.0012 (10)	0.0109 (8)	−0.0028 (13)

Geometric parameters (Å, º) top

O1—S1	1.4967 (14)	C8—H8B	0.9800
S1—N1	1.6652 (16)	C8—H8C	0.9800
S1—C7	1.8401 (19)	C9—H9A	0.9800
N1—C1	1.418 (2)	C9—H9B	0.9800
N1—H1	0.8800	C9—H9C	0.9800
C1—C6	1.388 (3)	C10—H10A	0.9800
C1—C2	1.390 (2)	C10—H10B	0.9800
C1—N1X	1.457 (16)	C10—H10C	0.9800
C2—C3	1.392 (2)	O1X—S1X	1.493 (12)
C2—H2	0.9500	S1X—N1X	1.681 (13)
C3—O2	1.375 (2)	S1X—C7X	1.828 (13)
C3—C4	1.381 (3)	N1X—H1X	0.8800
O2—C11	1.435 (2)	C7X—C8X	1.528 (16)
C11—H11A	0.9800	C7X—C10X	1.528 (16)
C11—H11B	0.9800	C7X—C9X	1.555 (15)
C11—H11C	0.9800	C8X—H8D	0.9800
C4—C5	1.381 (3)	C8X—H8E	0.9800
C4—H4	0.9500	C8X—H8F	0.9800
C5—C6	1.381 (3)	C9X—H9D	0.9800
C5—H5	0.9500	C9X—H9E	0.9800
C6—H6	0.9500	C9X—H9F	0.9800
C7—C9	1.522 (3)	C10X—H10D	0.9800
C7—C8	1.526 (3)	C10X—H10E	0.9800
C7—C10	1.534 (3)	C10X—H10F	0.9800
C8—H8A	0.9800

O1—S1—N1	108.28 (9)	H8B—C8—H8C	109.5
O1—S1—C7	106.04 (8)	C7—C9—H9A	109.5
N1—S1—C7	99.44 (9)	C7—C9—H9B	109.5
C1—N1—S1	121.54 (13)	H9A—C9—H9B	109.5
C1—N1—H1	119.2	C7—C9—H9C	109.5
S1—N1—H1	119.2	H9A—C9—H9C	109.5
C6—C1—C2	119.54 (16)	H9B—C9—H9C	109.5
C6—C1—N1	122.58 (16)	C7—C10—H10A	109.5
C2—C1—N1	117.88 (15)	C7—C10—H10B	109.5
C6—C1—N1X	114.7 (6)	H10A—C10—H10B	109.5
C2—C1—N1X	119.7 (6)	C7—C10—H10C	109.5
C1—C2—C3	119.86 (16)	H10A—C10—H10C	109.5
C1—C2—H2	120.1	H10B—C10—H10C	109.5
C3—C2—H2	120.1	O1X—S1X—N1X	111.3 (8)
O2—C3—C4	124.38 (16)	O1X—S1X—C7X	106.8 (8)
O2—C3—C2	114.58 (16)	N1X—S1X—C7X	97.7 (8)
C4—C3—C2	121.03 (17)	C1—N1X—S1X	127.0 (11)
C3—O2—C11	117.06 (16)	C1—N1X—H1X	116.5
O2—C11—H11A	109.5	S1X—N1X—H1X	116.5
O2—C11—H11B	109.5	C8X—C7X—C10X	112.9 (15)
H11A—C11—H11B	109.5	C8X—C7X—C9X	109.8 (14)
O2—C11—H11C	109.5	C10X—C7X—C9X	108.3 (16)
H11A—C11—H11C	109.5	C8X—C7X—S1X	107.4 (11)
H11B—C11—H11C	109.5	C10X—C7X—S1X	106.6 (14)
C5—C4—C3	117.97 (16)	C9X—C7X—S1X	111.8 (11)
C5—C4—H4	121.0	C7X—C8X—H8D	109.5
C3—C4—H4	121.0	C7X—C8X—H8E	109.5
C6—C5—C4	122.33 (17)	H8D—C8X—H8E	109.5
C6—C5—H5	118.8	C7X—C8X—H8F	109.5
C4—C5—H5	118.8	H8D—C8X—H8F	109.5
C5—C6—C1	119.20 (17)	H8E—C8X—H8F	109.5
C5—C6—H6	120.4	C7X—C9X—H9D	109.5
C1—C6—H6	120.4	C7X—C9X—H9E	109.5
C9—C7—C8	112.73 (17)	H9D—C9X—H9E	109.5
C9—C7—C10	111.27 (18)	C7X—C9X—H9F	109.5
C8—C7—C10	110.95 (19)	H9D—C9X—H9F	109.5
C9—C7—S1	111.54 (13)	H9E—C9X—H9F	109.5
C8—C7—S1	105.49 (13)	C7X—C10X—H10D	109.5
C10—C7—S1	104.40 (18)	C7X—C10X—H10E	109.5
C7—C8—H8A	109.5	H10D—C10X—H10E	109.5
C7—C8—H8B	109.5	C7X—C10X—H10F	109.5
H8A—C8—H8B	109.5	H10D—C10X—H10F	109.5
C7—C8—H8C	109.5	H10E—C10X—H10F	109.5
H8A—C8—H8C	109.5

O1—S1—N1—C1	−113.14 (17)	N1X—C1—C6—C5	−152.9 (8)
C7—S1—N1—C1	136.38 (17)	O1—S1—C7—C9	−59.63 (15)
S1—N1—C1—C6	−26.5 (3)	N1—S1—C7—C9	52.62 (15)
S1—N1—C1—C2	154.05 (16)	O1—S1—C7—C8	177.66 (12)
S1—N1—C1—N1X	−104.9 (15)	N1—S1—C7—C8	−70.09 (14)
C6—C1—C2—C3	−2.1 (3)	O1—S1—C7—C10	60.64 (17)
N1—C1—C2—C3	177.31 (18)	N1—S1—C7—C10	172.89 (16)
N1X—C1—C2—C3	149.0 (8)	C6—C1—N1X—S1X	−10.0 (16)
C1—C2—C3—O2	−177.99 (17)	C2—C1—N1X—S1X	−162.5 (9)
C1—C2—C3—C4	3.4 (3)	N1—C1—N1X—S1X	105 (2)
C4—C3—O2—C11	1.7 (3)	O1X—S1X—N1X—C1	125.7 (13)
C2—C3—O2—C11	−176.92 (19)	C7X—S1X—N1X—C1	−122.9 (14)
O2—C3—C4—C5	179.45 (19)	O1X—S1X—C7X—C8X	−178.2 (12)
C2—C3—C4—C5	−2.1 (3)	N1X—S1X—C7X—C8X	66.7 (13)
C3—C4—C5—C6	−0.5 (3)	O1X—S1X—C7X—C10X	−57.0 (15)
C4—C5—C6—C1	1.6 (3)	N1X—S1X—C7X—C10X	−172.0 (15)
C2—C1—C6—C5	−0.3 (3)	O1X—S1X—C7X—C9X	61.2 (14)
N1—C1—C6—C5	−179.7 (2)	N1X—S1X—C7X—C9X	−53.9 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.24	2.884 (2)	130
N1X—H1X···O1Xⁱⁱ	0.88	2.21	2.94 (2)	141

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇NO₂S
M_r	227.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	12.4068 (13), 7.3076 (8), 12.9230 (13)
β (°)	93.2992 (15)
V (Å³)	1169.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.37 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.911, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	10627, 2633, 2237
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.646

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.07
No. of reflections	2633
No. of parameters	166
No. of restraints	149
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.40

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.24	2.884 (2)	129.6
N1X—H1X···O1Xⁱⁱ	0.88	2.21	2.94 (2)	141.0

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

Acknowledgements

MD and AJB thank KAIST for financial assistance.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Datta, M., Buglass, A. J. & Elsegood, M. R. J. (2009). Acta Cryst. E65, o2823. Web of Science CSD CrossRef IUCr Journals Google Scholar
Datta, M., Buglass, A. J., Hong, C. S. & Lim, J. H. (2008). Acta Cryst. E64, o1393. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ferreira, F., Audoin, M. & Chemla, F. (2005). Chem. Eur. J. 11, 5269–5278. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sato, S., Yoshioka, T. & Tamura, C. (1975). Acta Cryst. B31, 1385–1392. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Schuckmann, W., Fuess, H., Mösinger, O. & Ried, W. (1978). Acta Cryst. B34, 1516–1520. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stretter, H., Krause, M. & Last, W.-D. (1969). Chem. Ber. 102, 3357–3363. Google Scholar