(2S)-Methyl 2-(p-toluenesulfonamido)propanoate.

The enanti-omerically pure title compound, C(11)H(15)NO(4)S, contains a pyramidal N atom with an S-N bond length of 1.6262 (8) Å. In the crystal, mol-ecules are linked to form chains parallel to the a axis by the hydrogen bond from NH to the carbonyl oxygen. C-H⋯O inter-actions are also present.

Related literature

For the applications of esters in the food and cosmetics industries, see: Soni et al. (2002 ▶). For their use as inter­mediates in the synthesis of heterocyclic compounds, see: Akhtar et al. (2007 ▶); Chen et al. (2007 ▶); Kucukguzel et al. (2007 ▶). For their use in the pharmaceutical industry, see: Iqbal & Chaudhry (2008 ▶). For the pharmacological activity of sulfonamides, see:Akhtar et al. (2008 ▶); Zareef et al. (2007 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C11H15NO4S

M = 257.30

Orthorhombic,

a = 7.1948 (2) Å

b = 11.2552 (3) Å

c = 15.3311 (4) Å

V = 1241.50 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 100 K

0.35 × 0.30 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur E diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.972, T max = 1.000 (expected range = 0.922–0.949)

55416 measured reflections

4284 independent reflections

4060 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.063

S = 1.05

4284 reflections

161 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.31 e Å−3

Absolute structure: Flack (1983 ▶), 1818 Friedel pairs

Flack parameter: 0.01 (4)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017371/hg2507sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017371/hg2507Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H15NO4S	Dx = 1.377 Mg m−3
Mr = 257.30	Melting point = 363–365 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 40101 reflections
a = 7.1948 (2) Å	θ = 2.2–32.6°
b = 11.2552 (3) Å	µ = 0.26 mm−1
c = 15.3311 (4) Å	T = 100 K
V = 1241.50 (6) Å3	Irregular block, colourless
Z = 4	0.35 × 0.30 × 0.20 mm
F(000) = 544

Oxford Diffraction Xcalibur E diffractometer	4284 independent reflections
Radiation source: fine-focus sealed tube	4060 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 16.1419 pixels mm-1	θmax = 32.0°, θmin = 2.2°
ω–scan	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −16→16
Tmin = 0.972, Tmax = 1.000	l = −22→22
55416 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.0628P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4284 reflections	Δρmax = 0.37 e Å−3
161 parameters	Δρmin = −0.31 e Å−3
0 restraints	Absolute structure: Flack (1983), 1818 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (4)

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.

	x	y	z	Uiso*/Ueq
S	0.77287 (3)	0.499255 (18)	0.576519 (12)	0.01308 (5)
O1	0.26383 (10)	0.24453 (5)	0.58832 (5)	0.01963 (14)
O2	0.29792 (10)	0.39044 (5)	0.68639 (4)	0.01622 (12)
O3	0.95092 (9)	0.44220 (6)	0.58061 (5)	0.02115 (14)
O4	0.70626 (11)	0.56695 (6)	0.64934 (4)	0.02111 (14)
C1	0.31824 (12)	0.34256 (7)	0.60812 (5)	0.01252 (14)
C2	0.42632 (12)	0.42436 (7)	0.54745 (5)	0.01322 (14)
H2	0.4070	0.5085	0.5662	0.016*
C3	0.36297 (14)	0.41083 (10)	0.45331 (6)	0.0239 (2)
H3A	0.4314	0.4668	0.4164	0.036*
H3B	0.2295	0.4275	0.4493	0.036*
H3C	0.3872	0.3295	0.4336	0.036*
C4	0.19070 (16)	0.32121 (10)	0.74852 (7)	0.0258 (2)
H4A	0.0614	0.3160	0.7288	0.039*
H4B	0.1950	0.3598	0.8058	0.039*
H4C	0.2433	0.2411	0.7529	0.039*
C5	0.77229 (12)	0.59314 (7)	0.48448 (5)	0.01268 (14)
C6	0.69566 (12)	0.70659 (7)	0.48923 (5)	0.01463 (14)
H6	0.6427	0.7348	0.5421	0.018*
C7	0.69813 (12)	0.77808 (7)	0.41487 (6)	0.01543 (15)
H7	0.6459	0.8555	0.4174	0.019*
C8	0.77573 (13)	0.73814 (7)	0.33690 (5)	0.01487 (15)
C9	0.84746 (13)	0.62251 (8)	0.33331 (6)	0.01649 (16)
H9	0.8974	0.5933	0.2801	0.020*
C10	0.84653 (12)	0.55006 (7)	0.40655 (6)	0.01525 (15)
H10	0.8959	0.4719	0.4037	0.018*
C11	0.78446 (17)	0.81761 (9)	0.25811 (6)	0.02262 (18)
H11A	0.6738	0.8683	0.2564	0.034*
H11B	0.7893	0.7689	0.2052	0.034*
H11C	0.8960	0.8674	0.2614	0.034*
N	0.62422 (10)	0.39329 (6)	0.55827 (5)	0.01262 (13)
H01	0.661 (2)	0.3437 (14)	0.5189 (10)	0.032 (4)*

	U11	U22	U33	U12	U13	U23
S	0.01306 (9)	0.01406 (8)	0.01212 (8)	−0.00207 (7)	−0.00239 (6)	0.00121 (7)
O1	0.0243 (3)	0.0136 (3)	0.0210 (3)	−0.0038 (2)	−0.0008 (3)	−0.0026 (2)
O2	0.0175 (3)	0.0183 (3)	0.0129 (3)	−0.0021 (2)	0.0007 (2)	−0.0013 (2)
O3	0.0131 (3)	0.0248 (3)	0.0256 (3)	−0.0009 (2)	−0.0058 (3)	0.0072 (3)
O4	0.0310 (4)	0.0199 (3)	0.0125 (3)	−0.0053 (3)	0.0004 (3)	−0.0036 (2)
C1	0.0109 (3)	0.0130 (3)	0.0137 (3)	0.0008 (3)	−0.0016 (3)	0.0000 (3)
C2	0.0113 (3)	0.0137 (3)	0.0146 (3)	0.0008 (3)	−0.0005 (3)	0.0020 (3)
C3	0.0167 (4)	0.0388 (5)	0.0163 (4)	−0.0023 (4)	−0.0046 (3)	0.0078 (4)
C4	0.0269 (5)	0.0319 (5)	0.0187 (4)	−0.0047 (4)	0.0050 (4)	0.0060 (4)
C5	0.0123 (3)	0.0128 (3)	0.0129 (3)	−0.0013 (3)	−0.0004 (3)	0.0003 (2)
C6	0.0141 (3)	0.0140 (3)	0.0158 (3)	0.0005 (3)	0.0016 (3)	−0.0013 (3)
C7	0.0145 (3)	0.0128 (3)	0.0190 (4)	0.0006 (3)	−0.0003 (3)	0.0004 (3)
C8	0.0150 (3)	0.0153 (3)	0.0143 (3)	−0.0032 (3)	−0.0031 (3)	0.0019 (3)
C9	0.0194 (4)	0.0164 (4)	0.0137 (4)	−0.0014 (3)	0.0022 (3)	−0.0011 (3)
C10	0.0167 (4)	0.0129 (3)	0.0162 (4)	0.0009 (3)	0.0014 (3)	−0.0012 (3)
C11	0.0299 (5)	0.0199 (4)	0.0180 (4)	−0.0044 (4)	−0.0027 (4)	0.0050 (3)
N	0.0112 (3)	0.0109 (3)	0.0157 (3)	0.0003 (2)	−0.0002 (2)	−0.0002 (2)

S—O4	1.4341 (7)	C9—C10	1.3878 (12)
S—O3	1.4344 (7)	C2—H2	1.0000
S—N	1.6262 (8)	C3—H3A	0.9800
S—C5	1.7628 (8)	C3—H3B	0.9800
O1—C1	1.2094 (10)	C3—H3C	0.9800
O2—C1	1.3235 (10)	C4—H4A	0.9800
O2—C4	1.4525 (11)	C4—H4B	0.9800
C1—C2	1.5223 (11)	C4—H4C	0.9800
C2—N	1.4755 (11)	C6—H6	0.9500
C2—C3	1.5213 (13)	C7—H7	0.9500
C5—C6	1.3929 (11)	C9—H9	0.9500
C5—C10	1.3956 (11)	C10—H10	0.9500
C6—C7	1.3955 (11)	C11—H11A	0.9800
C7—C8	1.3938 (12)	C11—H11B	0.9800
C8—C9	1.4012 (12)	C11—H11C	0.9800
C8—C11	1.5043 (12)	N—H01	0.865 (16)
O4—S—O3	120.15 (5)	C2—C3—H3B	109.5
O4—S—N	107.69 (4)	H3A—C3—H3B	109.5
O3—S—N	105.46 (4)	C2—C3—H3C	109.5
O4—S—C5	107.69 (4)	H3A—C3—H3C	109.5
O3—S—C5	107.79 (4)	H3B—C3—H3C	109.5
N—S—C5	107.48 (4)	O2—C4—H4A	109.5
C1—O2—C4	115.78 (7)	O2—C4—H4B	109.5
O1—C1—O2	124.28 (8)	H4A—C4—H4B	109.5
O1—C1—C2	124.32 (8)	O2—C4—H4C	109.5
O2—C1—C2	111.35 (7)	H4A—C4—H4C	109.5
N—C2—C3	111.84 (7)	H4B—C4—H4C	109.5
N—C2—C1	106.32 (7)	C5—C6—H6	120.6
C3—C2—C1	111.48 (7)	C7—C6—H6	120.6
C6—C5—C10	120.98 (7)	C8—C7—H7	119.3
C6—C5—S	120.57 (6)	C6—C7—H7	119.3
C10—C5—S	118.43 (6)	C10—C9—H9	119.6
C5—C6—C7	118.74 (7)	C8—C9—H9	119.6
C8—C7—C6	121.32 (7)	C9—C10—H10	120.3
C7—C8—C9	118.74 (7)	C5—C10—H10	120.3
C7—C8—C11	120.90 (8)	C8—C11—H11A	109.5
C9—C8—C11	120.36 (8)	C8—C11—H11B	109.5
C10—C9—C8	120.81 (8)	H11A—C11—H11B	109.5
C9—C10—C5	119.37 (8)	C8—C11—H11C	109.5
C2—N—S	118.70 (6)	H11A—C11—H11C	109.5
N—C2—H2	109.0	H11B—C11—H11C	109.5
C3—C2—H2	109.0	C2—N—H01	111.8 (10)
C1—C2—H2	109.0	S—N—H01	113.1 (10)
C2—C3—H3A	109.5
C4—O2—C1—O1	−4.64 (13)	C5—C6—C7—C8	−0.17 (13)
C4—O2—C1—C2	177.89 (8)	C6—C7—C8—C9	1.82 (13)
O1—C1—C2—N	−87.54 (10)	C6—C7—C8—C11	−177.58 (9)
O2—C1—C2—N	89.93 (8)	C7—C8—C9—C10	−1.88 (13)
O1—C1—C2—C3	34.58 (12)	C11—C8—C9—C10	177.52 (9)
O2—C1—C2—C3	−147.95 (8)	C8—C9—C10—C5	0.29 (13)
O4—S—C5—C6	−6.70 (9)	C6—C5—C10—C9	1.42 (13)
O3—S—C5—C6	−137.70 (7)	S—C5—C10—C9	−179.99 (7)
N—S—C5—C6	109.07 (7)	C3—C2—N—S	108.25 (8)
O4—S—C5—C10	174.70 (7)	C1—C2—N—S	−129.86 (6)
O3—S—C5—C10	43.70 (8)	O4—S—N—C2	52.67 (7)
N—S—C5—C10	−69.53 (8)	O3—S—N—C2	−177.90 (6)
C10—C5—C6—C7	−1.48 (13)	C5—S—N—C2	−63.10 (7)
S—C5—C6—C7	179.97 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N—H01···O1i	0.865 (16)	2.057 (16)	2.9097 (10)	168.6 (14)
C10—H10···O1i	0.95	2.62	3.3696 (11)	136
C9—H9···O2ii	0.95	2.63	3.4065 (11)	140
C7—H7···O3iii	0.95	2.67	3.6167 (11)	172
C4—H4C···O4iv	0.98	2.49	3.3453 (13)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H01⋯O1i	0.865 (16)	2.057 (16)	2.9097 (10)	168.6 (14)
C10—H10⋯O1i	0.95	2.62	3.3696 (11)	136
C9—H9⋯O2ii	0.95	2.63	3.4065 (11)	140
C7—H7⋯O3iii	0.95	2.67	3.6167 (11)	172
C4—H4C⋯O4iv	0.98	2.49	3.3453 (13)	145

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .