2,2,2-Trimethyl-N-(4-methyl­phenyl­sulfon­yl)acetamide

Gowda, B.T.; Foro, S.; Sowmya, B.P.; Nirmala, P.G.; Fuess, H.

doi:10.1107/S1600536808017790

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1274

doi:10.1107/S1600536808017790

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2,2,2-Trimethyl-N-(4-methylphenylsulfonyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b B. P. Sowmya,^a P. G. Nirmala ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 7 June 2008; accepted 12 June 2008; online 19 June 2008)

The bond parameters and conformations of the N—H and C=O bonds of the SO₂—NH—CO—C group in the title compound, C₁₂H₁₇NO₃S, anti to each other, are similar to what has been observed in related structures. The benzene ring and the SO₂—NH—CO—C group make a dihedral angle of 71.2 (1)°. Intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For related literature, see: Gowda et al. (2003 , 2007 , 2008 ).

Experimental

Crystal data

C₁₂H₁₇NO₃S
M_r = 255.34
Triclinic, $[P \overline 1]$
a = 6.695 (1) Å
b = 8.953 (2) Å
c = 12.040 (2) Å
α = 80.21 (1)°
β = 78.51 (1)°
γ = 88.98 (1)°
V = 696.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 299 (2) K
0.50 × 0.32 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.894, T_max = 0.978
8562 measured reflections
2827 independent reflections
1947 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.142
S = 1.02
2827 reflections
182 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.79 (3)	2.19 (3)	2.955 (2)	164 (3)
Symmetry code: (i) -x, -y+2, -z+2.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017790/rk2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017790/rk2096Isup2.hkl

checkCIF report

Comment top

The present work is a part of a study of the substituent effects on the solid state geometries of N–(aryl)–sulfonamides and substituted amides. The conformations of the N—H and C=O bonds of the SO₂—NH—CO—C group in N–(4–methylphenylsulfonyl)–2,2,2–trimethylacetamide, (I), are anti– to each other (Fig. 1), similar to that observed in N–(phenylsulfonyl)–2,2,2–trimethylacetamide, II, (Gowda et al., 2008). The bond parameters in I are similar to those in II, N–(aryl)–2,2,2–trimethylacetamides (Gowda et al., 2007) and 4–methylbenzenesulfonamide (Gowda et al., 2003). The packing diagram of molecules I shows the intermolecular hydrogen bonds N1—H1N···O1ⁱ which link the molecules into centrosymmetric dimers (Fig. 2). Symmetry code: (i) -x, -y+2, -z+2.

Related literature top

For related literature, see: Gowda et al. (2003, 2007, 2008).

Experimental top

The title compound was prepared by refluxing 4–methylbenzenesulfonamide with excess pivalyl chloride for about an hour on a water bath. The reaction mixture was cooled and poured into ice cold water. The resulting solid was separated, washed thoroughly with water and dissolved in warm sodium hydrogen carbonate solution. The title compound was precipitated by acidifying the filtered solution with glacial acetic acid. It was filtered, dried and recrystallized from ethanol. The purity of the compound was checked by determining its melting point. It was characterized by recording its IR– and NMR–spectra. Single crystals of the title compound were obtained from an ethanolic solution and used for X–ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXS97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii. Only one part of disordered moiety is shown.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines. Symmetry code: (i) -x, -y+2, -z+2.

2,2,2-Trimethyl-N-(4-methylphenylsulfonyl)acetamide top

Crystal data top

C₁₂H₁₇NO₃S	Z = 2
M_r = 255.34	F(000) = 272
Triclinic, P1	D_x = 1.217 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.695 (1) Å	Cell parameters from 1734 reflections
b = 8.953 (2) Å	θ = 2.3–28.0°
c = 12.040 (2) Å	µ = 0.23 mm⁻¹
α = 80.21 (1)°	T = 299 K
β = 78.51 (1)°	Plate, colourless
γ = 88.98 (1)°	0.50 × 0.32 × 0.10 mm
V = 696.8 (2) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2827 independent reflections
Radiation source: Fine–focus sealed tube	1947 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scans	θ_max = 26.4°, θ_min = 2.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −8→8
T_min = 0.894, T_max = 0.978	k = −11→11
8562 measured reflections	l = −14→15

Refinement top

Refinement on F²	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: Geom
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0808P)² + 0.1297P] where P = (F_o² + 2F_c²)/3
2827 reflections	(Δ/σ)_max = 0.038
182 parameters	Δρ_max = 0.33 e Å⁻³
3 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₂H₁₇NO₃S	γ = 88.98 (1)°
M_r = 255.34	V = 696.8 (2) Å³
Triclinic, P1	Z = 2
a = 6.695 (1) Å	Mo Kα radiation
b = 8.953 (2) Å	µ = 0.23 mm⁻¹
c = 12.040 (2) Å	T = 299 K
α = 80.21 (1)°	0.50 × 0.32 × 0.10 mm
β = 78.51 (1)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2827 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1947 reflections with I > 2σ(I)
T_min = 0.894, T_max = 0.978	R_int = 0.023
8562 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	3 restraints
wR(F²) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.33 e Å⁻³
2827 reflections	Δρ_min = −0.34 e Å⁻³
182 parameters

Special details top

Experimental. CrysAlis RED, Oxford Diffraction Ltd., 2007 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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 > 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)
C1	0.1874 (3)	0.8846 (2)	0.75440 (18)	0.0516 (5)
C2	0.3230 (3)	0.8778 (3)	0.65199 (19)	0.0594 (6)
H2	0.4609	0.8988	0.6453	0.071*
C3	0.2531 (4)	0.8401 (3)	0.5608 (2)	0.0683 (6)
H3	0.3445	0.8360	0.4923	0.082*
C4	0.0483 (4)	0.8079 (3)	0.5687 (2)	0.0709 (7)
C5	−0.0839 (4)	0.8185 (3)	0.6716 (3)	0.0791 (8)
H5	−0.2221	0.7987	0.6783	0.095*
C6	−0.0172 (3)	0.8569 (3)	0.7630 (2)	0.0678 (6)
H6	−0.1093	0.8643	0.8307	0.081*
C7	0.3855 (4)	1.2106 (3)	0.7911 (2)	0.0639 (6)
C8	0.3541 (4)	1.3752 (3)	0.8054 (2)	0.0701 (7)
C9A	0.1437 (11)	1.4233 (10)	0.7939 (9)	0.100 (3)	0.50
H9A	0.0464	1.3618	0.8524	0.120*	0.50
H9B	0.1219	1.4113	0.7195	0.120*	0.50
H9C	0.1274	1.5278	0.8025	0.120*	0.50
C10A	0.5538 (16)	1.4617 (14)	0.7800 (13)	0.177 (7)	0.50
H10A	0.6243	1.4556	0.7033	0.213*	0.50
H10B	0.6360	1.4187	0.8338	0.213*	0.50
H10C	0.5281	1.5660	0.7867	0.213*	0.50
C11A	0.3989 (18)	1.3949 (12)	0.9168 (9)	0.196 (10)	0.50
H11A	0.5374	1.3672	0.9193	0.235*	0.50
H11B	0.3084	1.3313	0.9777	0.235*	0.50
H11C	0.3802	1.4989	0.9262	0.235*	0.50
C9B	0.1959 (18)	1.4340 (12)	0.7407 (9)	0.261 (14)	0.50
H9D	0.0703	1.3790	0.7733	0.314*	0.50
H9E	0.2375	1.4234	0.6615	0.314*	0.50
H9F	0.1766	1.5393	0.7460	0.314*	0.50
C10B	0.4889 (17)	1.4674 (8)	0.6990 (9)	0.127 (4)	0.50
H10D	0.4484	1.4464	0.6310	0.152*	0.50
H10E	0.6287	1.4400	0.6971	0.152*	0.50
H10F	0.4742	1.5735	0.7022	0.152*	0.50
C11B	0.2711 (16)	1.3977 (11)	0.9308 (7)	0.099 (3)	0.50
H11D	0.3680	1.3606	0.9775	0.119*	0.50
H11E	0.1444	1.3427	0.9599	0.119*	0.50
H11F	0.2494	1.5035	0.9328	0.119*	0.50
C12	−0.0265 (5)	0.7606 (4)	0.4700 (3)	0.1004 (10)
H12A	−0.0457	0.6525	0.4840	0.120*
H12B	0.0722	0.7904	0.4002	0.120*
H12C	−0.1536	0.8087	0.4627	0.120*
N1	0.2641 (3)	1.1039 (2)	0.87314 (17)	0.0608 (5)
H1N	0.171 (4)	1.125 (3)	0.919 (2)	0.073*
O1	0.1327 (3)	0.85718 (17)	0.97613 (13)	0.0685 (5)
O2	0.4839 (2)	0.87466 (19)	0.86454 (14)	0.0702 (5)
O3	0.5046 (3)	1.1703 (2)	0.71397 (17)	0.0929 (6)
S1	0.27716 (8)	0.91984 (6)	0.87499 (4)	0.0559 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0458 (11)	0.0419 (10)	0.0596 (12)	0.0075 (8)	0.0015 (9)	−0.0024 (9)
C2	0.0520 (12)	0.0601 (13)	0.0604 (13)	0.0020 (10)	0.0012 (10)	−0.0089 (10)
C3	0.0722 (16)	0.0665 (15)	0.0615 (14)	0.0057 (12)	−0.0020 (12)	−0.0114 (11)
C4	0.0814 (17)	0.0575 (14)	0.0755 (16)	0.0051 (12)	−0.0248 (14)	−0.0057 (12)
C5	0.0550 (14)	0.0894 (19)	0.0890 (19)	0.0024 (13)	−0.0138 (14)	−0.0047 (15)
C6	0.0512 (13)	0.0781 (16)	0.0664 (15)	0.0075 (11)	0.0001 (11)	−0.0052 (12)
C7	0.0625 (14)	0.0571 (13)	0.0663 (14)	−0.0074 (11)	−0.0023 (12)	−0.0058 (11)
C8	0.0807 (17)	0.0509 (13)	0.0763 (16)	−0.0078 (12)	−0.0163 (13)	−0.0027 (11)
C9A	0.086 (4)	0.065 (4)	0.154 (8)	0.005 (3)	−0.031 (5)	−0.022 (4)
C10A	0.134 (8)	0.151 (9)	0.228 (14)	−0.094 (7)	0.083 (9)	−0.110 (10)
C11A	0.37 (3)	0.084 (6)	0.205 (15)	0.025 (12)	−0.223 (19)	−0.044 (8)
C9B	0.51 (3)	0.132 (10)	0.268 (18)	0.156 (15)	−0.32 (2)	−0.113 (11)
C10B	0.138 (8)	0.044 (3)	0.164 (9)	−0.010 (4)	0.031 (7)	0.006 (4)
C11B	0.152 (8)	0.055 (4)	0.091 (5)	−0.010 (4)	−0.010 (5)	−0.023 (4)
C12	0.124 (3)	0.088 (2)	0.099 (2)	0.0007 (19)	−0.048 (2)	−0.0169 (17)
N1	0.0642 (12)	0.0479 (10)	0.0605 (11)	0.0012 (8)	0.0108 (9)	−0.0086 (8)
O1	0.0794 (11)	0.0538 (9)	0.0583 (9)	0.0055 (8)	0.0097 (8)	0.0015 (7)
O2	0.0580 (10)	0.0762 (11)	0.0751 (11)	0.0184 (8)	−0.0113 (8)	−0.0134 (8)
O3	0.0956 (14)	0.0753 (12)	0.0865 (13)	−0.0155 (10)	0.0340 (11)	−0.0132 (10)
S1	0.0568 (4)	0.0479 (3)	0.0556 (3)	0.0077 (2)	0.0021 (2)	−0.0040 (2)

Geometric parameters (Å, º) top

C1—C6	1.377 (3)	C9A—H9C	0.9600
C1—C2	1.388 (3)	C10A—H10A	0.9600
C1—S1	1.755 (2)	C10A—H10B	0.9600
C2—C3	1.370 (3)	C10A—H10C	0.9600
C2—H2	0.9300	C11A—H11A	0.9600
C3—C4	1.387 (4)	C11A—H11B	0.9600
C3—H3	0.9300	C11A—H11C	0.9600
C4—C5	1.388 (4)	C9B—H9D	0.9600
C4—C12	1.503 (4)	C9B—H9E	0.9600
C5—C6	1.363 (4)	C9B—H9F	0.9600
C5—H5	0.9300	C10B—H10D	0.9600
C6—H6	0.9300	C10B—H10E	0.9600
C7—O3	1.199 (3)	C10B—H10F	0.9600
C7—N1	1.391 (3)	C11B—H11D	0.9600
C7—C8	1.519 (3)	C11B—H11E	0.9600
C8—C9B	1.474 (8)	C11B—H11F	0.9600
C8—C11A	1.471 (8)	C12—H12A	0.9600
C8—C9A	1.492 (7)	C12—H12B	0.9600
C8—C10A	1.508 (8)	C12—H12C	0.9600
C8—C10B	1.530 (7)	N1—S1	1.645 (2)
C8—C11B	1.548 (8)	N1—H1N	0.79 (3)
C9A—H9A	0.9600	O1—S1	1.4322 (15)
C9A—H9B	0.9600	O2—S1	1.4226 (16)

C6—C1—C2	119.9 (2)	H9C—C9A—H9D	124.4
C6—C1—S1	119.81 (17)	C8—C9A—H9F	99.8
C2—C1—S1	120.19 (17)	H9A—C9A—H9F	143.6
C3—C2—C1	119.7 (2)	H9B—C9A—H9F	79.1
C3—C2—H2	120.1	H9C—C9A—H9F	38.1
C1—C2—H2	120.1	H9D—C9A—H9F	115.2
C2—C3—C4	121.2 (2)	C8—C10A—H10A	109.5
C2—C3—H3	119.4	C8—C10A—H10B	109.5
C4—C3—H3	119.4	H10A—C10A—H10B	109.5
C3—C4—C5	117.6 (2)	C8—C10A—H10C	109.5
C3—C4—C12	121.0 (3)	H10A—C10A—H10C	109.5
C5—C4—C12	121.3 (3)	H10B—C10A—H10C	109.5
C6—C5—C4	122.0 (2)	C8—C11A—H11A	109.5
C6—C5—H5	119.0	C8—C11A—H11B	109.5
C4—C5—H5	119.0	H11A—C11A—H11B	109.5
C5—C6—C1	119.5 (2)	C8—C11A—H11C	109.5
C5—C6—H6	120.3	H11A—C11A—H11C	109.5
C1—C6—H6	120.3	H11B—C11A—H11C	109.5
O3—C7—N1	119.9 (2)	C8—C9B—H9D	109.6
O3—C7—C8	123.8 (2)	C8—C9B—H9E	110.1
N1—C7—C8	116.3 (2)	H9D—C9B—H9E	109.5
C9B—C8—C11A	133.9 (8)	C8—C9B—H9F	108.6
C9B—C8—C9A	25.6 (7)	H9D—C9B—H9F	109.5
C11A—C8—C9A	112.1 (6)	H9E—C9B—H9F	109.5
C9B—C8—C10A	118.0 (9)	C8—C10B—H10D	109.5
C11A—C8—C10A	73.2 (8)	C8—C10B—H10E	109.5
C9A—C8—C10A	132.1 (7)	H10D—C10B—H10E	109.5
C9B—C8—C7	106.9 (4)	C8—C10B—H10F	109.5
C11A—C8—C7	109.0 (4)	H10D—C10B—H10F	109.5
C9A—C8—C7	110.8 (4)	H10E—C10B—H10F	109.5
C10A—C8—C7	111.7 (5)	C8—C11B—H11D	109.5
C9B—C8—C10B	80.5 (7)	C8—C11B—H11E	109.5
C11A—C8—C10B	115.8 (8)	H11D—C11B—H11E	109.5
C9A—C8—C10B	103.5 (6)	C8—C11B—H11F	109.5
C10A—C8—C10B	44.0 (6)	H11D—C11B—H11F	109.5
C7—C8—C10B	105.3 (4)	H11E—C11B—H11F	109.5
C9B—C8—C11B	105.6 (7)	C4—C12—H12A	109.5
C11A—C8—C11B	32.2 (6)	C4—C12—H12B	109.5
C9A—C8—C11B	81.3 (6)	H12A—C12—H12B	109.5
C10A—C8—C11B	100.5 (6)	C4—C12—H12C	109.5
C7—C8—C11B	114.1 (4)	H12A—C12—H12C	109.5
C10B—C8—C11B	135.7 (5)	H12B—C12—H12C	109.5
C8—C9A—H9A	109.5	C7—N1—S1	124.02 (17)
C8—C9A—H9B	109.5	C7—N1—H1N	124.0 (19)
H9A—C9A—H9B	109.5	S1—N1—H1N	111.5 (19)
C8—C9A—H9C	109.5	O2—S1—O1	118.88 (10)
H9A—C9A—H9C	109.5	O2—S1—N1	109.50 (10)
H9B—C9A—H9C	109.5	O1—S1—N1	103.95 (9)
C8—C9A—H9D	125.1	O2—S1—C1	108.79 (10)
H9A—C9A—H9D	64.0	O1—S1—C1	108.34 (10)
H9B—C9A—H9D	45.5	N1—S1—C1	106.71 (10)

C6—C1—C2—C3	−1.5 (3)	N1—C7—C8—C10A	139.4 (7)
S1—C1—C2—C3	175.60 (17)	O3—C7—C8—C10B	4.5 (6)
C1—C2—C3—C4	−0.2 (4)	N1—C7—C8—C10B	−174.6 (5)
C2—C3—C4—C5	1.3 (4)	O3—C7—C8—C11B	−154.7 (5)
C2—C3—C4—C12	−177.6 (2)	N1—C7—C8—C11B	26.3 (5)
C3—C4—C5—C6	−0.9 (4)	O3—C7—N1—S1	2.2 (4)
C12—C4—C5—C6	178.0 (2)	C8—C7—N1—S1	−178.70 (17)
C4—C5—C6—C1	−0.8 (4)	C7—N1—S1—O2	49.4 (2)
C2—C1—C6—C5	2.0 (3)	C7—N1—S1—O1	177.46 (19)
S1—C1—C6—C5	−175.16 (18)	C7—N1—S1—C1	−68.1 (2)
O3—C7—C8—C9B	88.9 (6)	C6—C1—S1—O2	152.78 (18)
N1—C7—C8—C9B	−90.1 (6)	C2—C1—S1—O2	−24.3 (2)
O3—C7—C8—C11A	−120.5 (6)	C6—C1—S1—O1	22.2 (2)
N1—C7—C8—C11A	60.5 (6)	C2—C1—S1—O1	−154.90 (17)
O3—C7—C8—C9A	115.7 (5)	C6—C1—S1—N1	−89.16 (19)
N1—C7—C8—C9A	−63.3 (5)	C2—C1—S1—N1	93.72 (18)
O3—C7—C8—C10A	−41.6 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.79 (3)	2.19 (3)	2.955 (2)	164 (3)

Symmetry code: (i) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₇NO₃S
M_r	255.34
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	6.695 (1), 8.953 (2), 12.040 (2)
α, β, γ (°)	80.21 (1), 78.51 (1), 88.98 (1)
V (Å³)	696.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.50 × 0.32 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.894, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	8562, 2827, 1947
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.142, 1.02
No. of reflections	2827
No. of parameters	182
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.34

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.79 (3)	2.19 (3)	2.955 (2)	164 (3)

Symmetry code: (i) −x, −y+2, −z+2.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

Gowda, B. T., Foro, S., Sowmya, B. P., Nirmala, P. G. & Fuess, H. (2008). Acta Cryst. E64. Submitted. CrossRef IUCr Journals Google Scholar
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Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
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