(2S)-Methyl 2-(4-chloro-benzene-sulfon-amido)-4-(methyl-sulfan-yl)butanoate.

The enanti-omerically pure title compound, C(12)H(16)ClNO(4)S(2), contains a pyramidal N atom with an S-N bond length of 1.6306 (15) Å. Mol-ecules are linked to form chains parallel to the a axis by classical N-H⋯O hydrogen bonding involving a sulfonyl O atom, supported by three weak C-H⋯X inter-actions. (X = S, O).

Related literature

For the applications of esters in industry and as inter­mediates in the synthesis of heterocycles, see: Akhtar et al. (2007 ▶, 2008 ▶); Kashif et al. (2008 ▶); Serwar et al. (2009 ▶); Syed et al. (2009 ▶).

Experimental

Crystal data

C12H16ClNO4S2

M = 337.83

Orthorhombic,

a = 5.1814 (3) Å

b = 12.6089 (8) Å

c = 23.2137 (13) Å

V = 1516.59 (16) Å3

Z = 4

Cu Kα radiation

μ = 4.92 mm−1

T = 100 K

0.20 × 0.12 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur Nova A diffractometer

Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2008 ▶) T min = 0.548, T max = 1.000 (expected range = 0.408–0.744)

14469 measured reflections

3093 independent reflections

3027 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.062

S = 1.04

3093 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 1250 Friedel pairs

Flack parameter: 0.005 (12)

Data collection: CrysAlis Pro (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; 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/S1600536809018297/bt2959sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018297/bt2959Isup2.hkl

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

C12H16ClNO4S2	Dx = 1.480 Mg m−3
Mr = 337.83	Melting point = 331–333 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
a = 5.1814 (3) Å	Cell parameters from 10903 reflections
b = 12.6089 (8) Å	θ = 3.5–75.6°
c = 23.2137 (13) Å	µ = 4.92 mm−1
V = 1516.59 (16) Å3	T = 100 K
Z = 4	Tablet, colourless
F(000) = 704	0.20 × 0.12 × 0.06 mm

Oxford Diffraction Xcalibur Nova A diffractometer	3093 independent reflections
Radiation source: Nova (Cu) X-ray Source	3027 reflections with I > 2σ(I)
mirror	Rint = 0.033
Detector resolution: 10.3543 pixels mm-1	θmax = 75.7°, θmin = 3.8°
ω scans	h = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2008)	k = −15→15
Tmin = 0.548, Tmax = 1.000	l = −29→27
14469 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)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.062	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.6444P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
3093 reflections	Δρmax = 0.20 e Å−3
187 parameters	Δρmin = −0.35 e Å−3
0 restraints	Absolute structure: Flack (1983), 1250 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.005 (12)

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
C1	0.6060 (3)	0.70856 (13)	0.30125 (7)	0.0157 (3)
C2	0.7658 (3)	0.64578 (13)	0.25767 (7)	0.0149 (3)
H2	0.9529	0.6527	0.2676	0.018*
C3	0.7198 (3)	0.69178 (13)	0.19720 (7)	0.0157 (3)
H3A	0.5399	0.6770	0.1853	0.019*
H3B	0.7427	0.7697	0.1984	0.019*
C4	0.9040 (3)	0.64498 (13)	0.15292 (7)	0.0175 (3)
H4A	0.8724	0.5677	0.1501	0.021*
H4B	1.0834	0.6552	0.1665	0.021*
C5	0.5616 (4)	0.65296 (18)	0.06022 (8)	0.0279 (4)
H5A	0.5565	0.5761	0.0662	0.042*
H5B	0.5334	0.6687	0.0194	0.042*
H5C	0.4261	0.6868	0.0833	0.042*
C6	0.5679 (4)	0.87023 (14)	0.34955 (8)	0.0267 (4)
H6A	0.3949	0.8791	0.3332	0.040*
H6B	0.6529	0.9395	0.3522	0.040*
H6C	0.5541	0.8390	0.3881	0.040*
C11	0.7949 (3)	0.48637 (13)	0.37042 (7)	0.0166 (3)
C12	0.9359 (3)	0.56678 (13)	0.39648 (7)	0.0194 (3)
H12	1.0801	0.5972	0.3774	0.023*
C13	0.8635 (4)	0.60215 (14)	0.45083 (8)	0.0230 (3)
H13	0.9576	0.6570	0.4694	0.028*
C14	0.6511 (4)	0.55597 (14)	0.47751 (7)	0.0225 (3)
C15	0.5128 (4)	0.47418 (15)	0.45226 (8)	0.0224 (4)
H15	0.3716	0.4425	0.4719	0.027*
C16	0.5837 (3)	0.43950 (13)	0.39798 (7)	0.0192 (3)
H16	0.4898	0.3843	0.3796	0.023*
O1	0.4034 (3)	0.67950 (10)	0.32058 (5)	0.0225 (3)
O2	0.7177 (2)	0.80112 (10)	0.31298 (5)	0.0202 (3)
O3	1.1274 (2)	0.47165 (9)	0.28709 (5)	0.0187 (2)
O4	0.7538 (2)	0.34783 (10)	0.28792 (5)	0.0199 (3)
S1	0.87182 (9)	0.70331 (3)	0.081959 (17)	0.02100 (10)
S2	0.86006 (8)	0.45109 (3)	0.298219 (16)	0.01470 (9)
Cl	0.55423 (10)	0.60320 (4)	0.54465 (2)	0.03195 (12)
N	0.6935 (3)	0.53293 (11)	0.25852 (6)	0.0151 (3)
H01	0.540 (6)	0.521 (2)	0.2616 (12)	0.041 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0189 (8)	0.0141 (7)	0.0140 (7)	0.0002 (7)	−0.0010 (7)	0.0023 (6)
C2	0.0149 (7)	0.0120 (7)	0.0176 (8)	−0.0009 (6)	−0.0006 (6)	−0.0011 (6)
C3	0.0160 (7)	0.0143 (7)	0.0168 (8)	0.0003 (6)	−0.0005 (6)	0.0005 (6)
C4	0.0157 (8)	0.0201 (8)	0.0168 (7)	0.0025 (6)	0.0004 (6)	0.0016 (6)
C5	0.0225 (9)	0.0396 (10)	0.0216 (9)	0.0020 (8)	−0.0013 (7)	0.0023 (8)
C6	0.0365 (11)	0.0214 (8)	0.0223 (8)	0.0063 (8)	0.0019 (8)	−0.0074 (7)
C11	0.0165 (8)	0.0140 (7)	0.0192 (8)	0.0022 (6)	−0.0011 (6)	0.0035 (6)
C12	0.0187 (8)	0.0184 (8)	0.0212 (8)	−0.0017 (6)	0.0012 (6)	0.0032 (6)
C13	0.0266 (9)	0.0195 (8)	0.0228 (8)	−0.0008 (8)	−0.0022 (8)	−0.0008 (7)
C14	0.0259 (9)	0.0222 (8)	0.0194 (8)	0.0043 (8)	0.0005 (7)	0.0026 (6)
C15	0.0211 (8)	0.0249 (8)	0.0211 (8)	−0.0006 (7)	0.0031 (7)	0.0068 (7)
C16	0.0189 (8)	0.0168 (8)	0.0219 (8)	−0.0030 (7)	−0.0019 (7)	0.0025 (6)
O1	0.0205 (7)	0.0197 (6)	0.0272 (6)	−0.0006 (5)	0.0076 (5)	−0.0008 (5)
O2	0.0254 (6)	0.0149 (6)	0.0204 (6)	−0.0018 (5)	0.0014 (5)	−0.0049 (5)
O3	0.0154 (5)	0.0161 (5)	0.0246 (6)	0.0007 (5)	0.0006 (5)	−0.0021 (4)
O4	0.0214 (6)	0.0126 (6)	0.0256 (6)	−0.0028 (5)	0.0000 (5)	−0.0004 (5)
S1	0.01868 (19)	0.0276 (2)	0.01674 (19)	0.00114 (18)	0.00273 (16)	0.00482 (15)
S2	0.01470 (18)	0.01144 (17)	0.01797 (18)	−0.00017 (15)	0.00043 (15)	0.00026 (13)
Cl	0.0416 (3)	0.0336 (2)	0.0206 (2)	0.0050 (2)	0.00561 (18)	−0.00285 (18)
N	0.0140 (6)	0.0128 (6)	0.0186 (7)	−0.0027 (5)	−0.0002 (5)	0.0000 (5)

C1—O1	1.199 (2)	O4—S2	1.4337 (13)
C1—O2	1.331 (2)	S2—N	1.6306 (15)
C1—C2	1.528 (2)	C2—H2	1.0000
C2—N	1.472 (2)	C3—H3A	0.9900
C2—C3	1.538 (2)	C3—H3B	0.9900
C3—C4	1.522 (2)	C4—H4A	0.9900
C4—S1	1.8117 (17)	C4—H4B	0.9900
C5—S1	1.800 (2)	C5—H5A	0.9800
C6—O2	1.443 (2)	C5—H5B	0.9800
C11—C12	1.388 (2)	C5—H5C	0.9800
C11—C16	1.398 (2)	C6—H6A	0.9800
C11—S2	1.7667 (18)	C6—H6B	0.9800
C12—C13	1.390 (2)	C6—H6C	0.9800
C13—C14	1.391 (3)	C12—H12	0.9500
C14—C15	1.386 (3)	C13—H13	0.9500
C14—Cl	1.7422 (18)	C15—H15	0.9500
C15—C16	1.384 (2)	C16—H16	0.9500
O3—S2	1.4327 (13)	N—H01	0.81 (3)
O1—C1—O2	124.89 (16)	C2—C3—H3A	109.2
O1—C1—C2	124.31 (15)	C4—C3—H3B	109.2
O2—C1—C2	110.75 (14)	C2—C3—H3B	109.2
N—C2—C1	110.74 (13)	H3A—C3—H3B	107.9
N—C2—C3	109.73 (13)	C3—C4—H4A	108.9
C1—C2—C3	108.97 (13)	S1—C4—H4A	108.9
C4—C3—C2	111.92 (14)	C3—C4—H4B	108.9
C3—C4—S1	113.52 (11)	S1—C4—H4B	108.9
C12—C11—C16	121.41 (16)	H4A—C4—H4B	107.7
C12—C11—S2	119.77 (13)	S1—C5—H5A	109.5
C16—C11—S2	118.50 (13)	S1—C5—H5B	109.5
C11—C12—C13	119.20 (17)	H5A—C5—H5B	109.5
C12—C13—C14	118.92 (17)	S1—C5—H5C	109.5
C15—C14—C13	122.17 (17)	H5A—C5—H5C	109.5
C15—C14—Cl	118.93 (14)	H5B—C5—H5C	109.5
C13—C14—Cl	118.90 (14)	O2—C6—H6A	109.5
C16—C15—C14	118.88 (17)	O2—C6—H6B	109.5
C15—C16—C11	119.40 (16)	H6A—C6—H6B	109.5
C1—O2—C6	114.59 (14)	O2—C6—H6C	109.5
C5—S1—C4	101.18 (9)	H6A—C6—H6C	109.5
O3—S2—O4	120.36 (7)	H6B—C6—H6C	109.5
O3—S2—N	107.18 (7)	C11—C12—H12	120.4
O4—S2—N	106.09 (7)	C13—C12—H12	120.4
O3—S2—C11	108.08 (8)	C12—C13—H13	120.5
O4—S2—C11	108.27 (8)	C14—C13—H13	120.5
N—S2—C11	106.00 (7)	C16—C15—H15	120.6
C2—N—S2	118.99 (11)	C14—C15—H15	120.6
N—C2—H2	109.1	C15—C16—H16	120.3
C1—C2—H2	109.1	C11—C16—H16	120.3
C3—C2—H2	109.1	C2—N—H01	115.6 (19)
C4—C3—H3A	109.2	S2—N—H01	110.5 (19)
O1—C1—C2—N	−20.6 (2)	S2—C11—C16—C15	−173.17 (13)
O2—C1—C2—N	161.73 (13)	O1—C1—O2—C6	−3.3 (2)
O1—C1—C2—C3	100.19 (18)	C2—C1—O2—C6	174.33 (14)
O2—C1—C2—C3	−77.48 (16)	C3—C4—S1—C5	−69.77 (14)
N—C2—C3—C4	−67.63 (17)	C12—C11—S2—O3	29.75 (15)
C1—C2—C3—C4	170.97 (14)	C16—C11—S2—O3	−156.70 (13)
C2—C3—C4—S1	−176.06 (11)	C12—C11—S2—O4	161.63 (13)
C16—C11—C12—C13	−0.7 (3)	C16—C11—S2—O4	−24.82 (15)
S2—C11—C12—C13	172.62 (13)	C12—C11—S2—N	−84.90 (15)
C11—C12—C13—C14	−0.1 (3)	C16—C11—S2—N	88.66 (14)
C12—C13—C14—C15	1.5 (3)	C1—C2—N—S2	−94.83 (15)
C12—C13—C14—Cl	−177.99 (13)	C3—C2—N—S2	144.83 (12)
C13—C14—C15—C16	−2.0 (3)	O3—S2—N—C2	−47.30 (14)
Cl—C14—C15—C16	177.52 (14)	O4—S2—N—C2	−177.08 (12)
C14—C15—C16—C11	1.1 (3)	C11—S2—N—C2	67.96 (14)
C12—C11—C16—C15	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H01···O3i	0.81 (3)	2.30 (3)	3.1048 (18)	169 (3)
C2—H2···O1ii	1.00	2.66	3.637 (2)	166
C12—H12···O1ii	0.95	2.37	3.315 (2)	173
C3—H3B···O3iii	0.99	2.66	3.635 (2)	170
C5—H5B···S1iv	0.98	2.97	3.892 (2)	157
C5—H5C···S1i	0.98	2.88	3.665 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H01⋯O3i	0.81 (3)	2.30 (3)	3.1048 (18)	169 (3)
C2—H2⋯O1ii	1.00	2.66	3.637 (2)	166
C12—H12⋯O1ii	0.95	2.37	3.315 (2)	173
C3—H3B⋯O3iii	0.99	2.66	3.635 (2)	170
C5—H5B⋯S1iv	0.98	2.97	3.892 (2)	157
C5—H5C⋯S1i	0.98	2.88	3.665 (2)	138

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