Ethyl 2-benzene-sulfonamido-4-methyl-penta-noate.

In the title compound, C(14)H(21)NO(4)S, the O-S-O angle is 120.06 (11)°, with the S atom adopting a distorted tetra-hedral geometry. In the crystal, N-H⋯O hydrogen bonds connect the mol-ecules along the a axis, generating an infinite chain. The disordered C atoms of the isobutyl group were refined with the C-C distances restrained to 1.52 (1) Å and the occupancy ratio refined to 0.504 (3):0.496 (3).

Related literature

For related structures, see: Arshad et al. (2010 ▶, 2012 ▶).

Experimental

Crystal data

C14H21NO4S

M = 299.38

Orthorhombic,

a = 5.3084 (3) Å

b = 9.5507 (7) Å

c = 31.315 (2) Å

V = 1587.66 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.41 × 0.37 × 0.34 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.917, T max = 0.930

12652 measured reflections

3081 independent reflections

2701 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.098

S = 1.04

3081 reflections

223 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1220 Friedel pairs

Flack parameter: 0.01 (9)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and X-SEED (Barbour, 2001 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037658/bt5998sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037658/bt5998Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037658/bt5998Isup3.cml

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

C14H21NO4S	F(000) = 640
Mr = 299.38	Dx = 1.252 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5078 reflections
a = 5.3084 (3) Å	θ = 2.5–24.4°
b = 9.5507 (7) Å	µ = 0.22 mm−1
c = 31.315 (2) Å	T = 296 K
V = 1587.66 (19) Å3	Prismatic, yellow
Z = 4	0.41 × 0.37 × 0.34 mm

Bruker Kappa APEXII CCD diffractometer	3081 independent reflections
Radiation source: fine-focus sealed tube	2701 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −6→6
Tmin = 0.917, Tmax = 0.930	k = −10→11
12652 measured reflections	l = −38→37

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.2498P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3081 reflections	Δρmax = 0.17 e Å−3
223 parameters	Δρmin = −0.23 e Å−3
4 restraints	Absolute structure: Flack (1983), 1220 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (9)

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 > 2sigma(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	Occ. (<1)
S1	0.68578 (10)	−0.19267 (6)	0.10068 (2)	0.05767 (18)
O1	0.4508 (3)	−0.18269 (19)	0.12304 (6)	0.0735 (5)
O2	0.7870 (4)	−0.32649 (16)	0.09014 (6)	0.0778 (5)
O3	0.9729 (3)	0.16642 (16)	0.09996 (6)	0.0655 (4)
O4	0.6446 (3)	0.22241 (16)	0.14150 (5)	0.0570 (4)
N1	0.8935 (3)	−0.11735 (19)	0.13029 (6)	0.0536 (5)
H1	1.0426	−0.1524	0.1315	0.064*
C1	0.6547 (4)	−0.0963 (2)	0.05333 (7)	0.0527 (5)
C2	0.8230 (5)	−0.1196 (3)	0.02036 (9)	0.0683 (7)
H2	0.9491	−0.1866	0.0232	0.082*
C3	0.8025 (6)	−0.0431 (3)	−0.01669 (9)	0.0783 (8)
H3	0.9157	−0.0582	−0.0389	0.094*
C4	0.6176 (6)	0.0547 (3)	−0.02112 (9)	0.0784 (8)
H4	0.6048	0.1058	−0.0463	0.094*
C5	0.4501 (6)	0.0782 (3)	0.01152 (9)	0.0757 (8)
H5	0.3238	0.1448	0.0083	0.091*
C6	0.4679 (5)	0.0031 (2)	0.04935 (9)	0.0626 (6)
H6	0.3558	0.0195	0.0716	0.075*
C7	0.8389 (4)	0.0075 (2)	0.15512 (7)	0.0510 (5)
H7A	0.6742	−0.0049	0.1687	0.061*	0.504 (3)
H7B	0.6744	−0.0049	0.1688	0.061*	0.496 (3)
C8	0.8294 (4)	0.1402 (2)	0.12817 (7)	0.0478 (5)
C9	0.6135 (5)	0.3561 (3)	0.11924 (8)	0.0707 (7)
H9A	0.5766	0.3403	0.0893	0.085*
H9B	0.7665	0.4112	0.1213	0.085*
C10	0.4024 (5)	0.4301 (3)	0.13998 (9)	0.0724 (7)
H10A	0.2535	0.3732	0.1385	0.109*
H10B	0.3728	0.5173	0.1256	0.109*
H10C	0.4434	0.4478	0.1693	0.109*
C11A	1.0382 (19)	0.0138 (11)	0.1901 (3)	0.060 (3)	0.504 (3)
H11A	1.2049	0.0103	0.1775	0.072*	0.504 (3)
H11B	1.0227	0.1010	0.2058	0.072*	0.504 (3)
C12A	1.0033 (10)	−0.1090 (5)	0.22027 (16)	0.0621 (13)	0.504 (3)
H12A	1.0898	−0.1889	0.2072	0.074*	0.504 (3)
C13A	1.1548 (15)	−0.0698 (8)	0.2604 (2)	0.109 (3)	0.504 (3)
H13A	1.3229	−0.0439	0.2522	0.164*	0.504 (3)
H13B	1.1612	−0.1486	0.2793	0.164*	0.504 (3)
H13C	1.0751	0.0076	0.2745	0.164*	0.504 (3)
C14A	0.7472 (11)	−0.1593 (7)	0.23266 (19)	0.088 (2)	0.504 (3)
H14A	0.6591	−0.1909	0.2077	0.131*	0.504 (3)
H14B	0.6551	−0.0840	0.2457	0.131*	0.504 (3)
H14C	0.7628	−0.2351	0.2526	0.131*	0.504 (3)
C11B	1.034 (3)	0.0378 (12)	0.1901 (3)	0.075 (4)	0.496 (3)
H11C	1.0500	−0.0496	0.2056	0.090*	0.496 (3)
H11D	1.1919	0.0496	0.1748	0.090*	0.496 (3)
C12B	1.0376 (9)	0.1504 (5)	0.22429 (16)	0.0629 (14)	0.496 (3)
H12B	1.0034	0.2396	0.2100	0.076*	0.496 (3)
C13B	0.8197 (16)	0.1219 (9)	0.2529 (2)	0.123 (3)	0.496 (3)
H13D	0.6658	0.1310	0.2370	0.185*	0.496 (3)
H13E	0.8201	0.1877	0.2761	0.185*	0.496 (3)
H13F	0.8327	0.0285	0.2640	0.185*	0.496 (3)
C14B	1.2773 (13)	0.1690 (8)	0.2491 (2)	0.099 (2)	0.496 (3)
H14D	1.4122	0.1911	0.2298	0.149*	0.496 (3)
H14E	1.3159	0.0840	0.2640	0.149*	0.496 (3)
H14F	1.2570	0.2439	0.2692	0.149*	0.496 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0400 (3)	0.0384 (3)	0.0946 (4)	−0.0045 (2)	0.0071 (3)	0.0040 (3)
O1	0.0384 (8)	0.0736 (12)	0.1084 (13)	−0.0082 (8)	0.0124 (8)	0.0184 (11)
O2	0.0729 (11)	0.0343 (9)	0.1263 (15)	−0.0015 (8)	0.0013 (11)	−0.0036 (9)
O3	0.0647 (10)	0.0535 (10)	0.0784 (10)	−0.0005 (8)	0.0242 (9)	0.0123 (8)
O4	0.0584 (9)	0.0451 (8)	0.0674 (9)	0.0129 (8)	0.0097 (8)	0.0148 (7)
N1	0.0340 (9)	0.0432 (10)	0.0836 (12)	0.0074 (8)	0.0088 (9)	0.0030 (9)
C1	0.0395 (11)	0.0409 (11)	0.0778 (14)	−0.0056 (9)	0.0017 (11)	−0.0087 (10)
C2	0.0552 (13)	0.0550 (14)	0.0947 (18)	0.0057 (13)	0.0089 (15)	−0.0115 (13)
C3	0.0778 (18)	0.085 (2)	0.0726 (16)	−0.0104 (19)	0.0109 (16)	−0.0110 (15)
C4	0.080 (2)	0.082 (2)	0.0730 (16)	−0.0125 (17)	−0.0117 (15)	0.0004 (15)
C5	0.0655 (16)	0.0669 (17)	0.0948 (19)	0.0050 (14)	−0.0179 (15)	0.0024 (15)
C6	0.0457 (13)	0.0556 (14)	0.0865 (17)	0.0043 (11)	0.0018 (12)	−0.0048 (13)
C7	0.0421 (11)	0.0433 (12)	0.0675 (12)	0.0079 (11)	0.0164 (10)	0.0092 (10)
C8	0.0422 (10)	0.0406 (11)	0.0606 (11)	−0.0042 (10)	0.0028 (11)	0.0013 (9)
C9	0.0836 (19)	0.0505 (13)	0.0781 (15)	0.0187 (13)	0.0113 (14)	0.0189 (12)
C10	0.0731 (17)	0.0505 (14)	0.0934 (18)	0.0137 (13)	0.0052 (15)	0.0107 (13)
C11A	0.086 (6)	0.036 (4)	0.057 (5)	0.014 (3)	0.016 (4)	0.002 (3)
C12A	0.061 (3)	0.054 (3)	0.071 (3)	0.005 (2)	−0.006 (2)	0.015 (2)
C13A	0.115 (6)	0.112 (5)	0.101 (4)	−0.035 (5)	−0.060 (5)	0.047 (4)
C14A	0.076 (4)	0.102 (5)	0.084 (4)	−0.003 (3)	−0.003 (3)	0.043 (3)
C11B	0.120 (9)	0.044 (5)	0.060 (6)	0.028 (5)	−0.023 (5)	0.008 (4)
C12B	0.058 (3)	0.051 (3)	0.080 (3)	0.007 (2)	0.008 (3)	−0.003 (2)
C13B	0.104 (5)	0.140 (7)	0.126 (6)	−0.042 (6)	0.058 (5)	−0.068 (5)
C14B	0.080 (4)	0.120 (6)	0.097 (4)	0.007 (4)	−0.023 (3)	−0.033 (4)

S1—O2	1.4251 (17)	C10—H10A	0.9600
S1—O1	1.4336 (16)	C10—H10B	0.9600
S1—N1	1.6104 (19)	C10—H10C	0.9600
S1—C1	1.753 (2)	C11A—C12A	1.517 (9)
O3—C8	1.193 (2)	C11A—H11A	0.9700
O4—C8	1.324 (3)	C11A—H11B	0.9700
O4—C9	1.464 (3)	C12A—C14A	1.493 (8)
N1—C7	1.453 (3)	C12A—C13A	1.537 (7)
N1—H1	0.8600	C12A—H12A	0.9800
C1—C6	1.378 (3)	C13A—H13A	0.9600
C1—C2	1.383 (3)	C13A—H13B	0.9600
C2—C3	1.376 (4)	C13A—H13C	0.9600
C2—H2	0.9300	C14A—H14A	0.9600
C3—C4	1.362 (4)	C14A—H14B	0.9600
C3—H3	0.9300	C14A—H14C	0.9600
C4—C5	1.373 (4)	C11B—C12B	1.519 (9)
C4—H4	0.9300	C11B—H11C	0.9700
C5—C6	1.388 (4)	C11B—H11D	0.9700
C5—H5	0.9300	C12B—C13B	1.488 (8)
C6—H6	0.9300	C12B—C14B	1.501 (8)
C7—C8	1.523 (3)	C12B—H12B	0.9800
C7—C11A	1.524 (7)	C13B—H13D	0.9600
C7—C11B	1.535 (8)	C13B—H13E	0.9600
C7—H7A	0.9800	C13B—H13F	0.9600
C7—H7B	0.9800	C14B—H14D	0.9600
C9—C10	1.475 (4)	C14B—H14E	0.9600
C9—H9A	0.9700	C14B—H14F	0.9600
C9—H9B	0.9700
O2—S1—O1	120.06 (11)	O4—C9—H9A	110.3
O2—S1—N1	106.01 (10)	C10—C9—H9A	110.3
O1—S1—N1	106.54 (11)	O4—C9—H9B	110.3
O2—S1—C1	108.08 (11)	C10—C9—H9B	110.3
O1—S1—C1	107.24 (11)	H9A—C9—H9B	108.6
N1—S1—C1	108.49 (10)	C9—C10—H10A	109.5
C8—O4—C9	116.81 (17)	C9—C10—H10B	109.5
C7—N1—S1	122.57 (14)	H10A—C10—H10B	109.5
C7—N1—H1	118.7	C9—C10—H10C	109.5
S1—N1—H1	118.7	H10A—C10—H10C	109.5
C6—C1—C2	120.5 (2)	H10B—C10—H10C	109.5
C6—C1—S1	120.38 (18)	C12A—C11A—C7	109.4 (6)
C2—C1—S1	119.06 (18)	C12A—C11A—H11A	109.8
C3—C2—C1	119.5 (3)	C7—C11A—H11A	109.8
C3—C2—H2	120.3	C12A—C11A—H11B	109.8
C1—C2—H2	120.3	C7—C11A—H11B	109.8
C4—C3—C2	120.5 (3)	H11A—C11A—H11B	108.2
C4—C3—H3	119.7	C14A—C12A—C11A	121.4 (5)
C2—C3—H3	119.7	C14A—C12A—C13A	110.0 (5)
C3—C4—C5	120.2 (3)	C11A—C12A—C13A	104.9 (5)
C3—C4—H4	119.9	C14A—C12A—H12A	106.5
C5—C4—H4	119.9	C11A—C12A—H12A	106.5
C4—C5—C6	120.5 (3)	C13A—C12A—H12A	106.5
C4—C5—H5	119.8	C12B—C11B—C7	130.2 (8)
C6—C5—H5	119.8	C12B—C11B—H11C	104.7
C1—C6—C5	118.8 (2)	C7—C11B—H11C	104.7
C1—C6—H6	120.6	C12B—C11B—H11D	104.7
C5—C6—H6	120.6	C7—C11B—H11D	104.7
N1—C7—C8	113.15 (17)	H11C—C11B—H11D	105.7
N1—C7—C11A	106.2 (5)	C13B—C12B—C14B	111.7 (5)
C8—C7—C11A	112.9 (4)	C13B—C12B—C11B	106.6 (7)
N1—C7—C11B	113.7 (5)	C14B—C12B—C11B	117.3 (6)
C8—C7—C11B	105.1 (5)	C13B—C12B—H12B	106.9
C11A—C7—C11B	8.6 (8)	C14B—C12B—H12B	106.9
N1—C7—H7A	108.2	C11B—C12B—H12B	106.9
C8—C7—H7A	108.2	C12B—C13B—H13D	109.5
C11A—C7—H7A	108.2	C12B—C13B—H13E	109.5
C11B—C7—H7A	108.4	H13D—C13B—H13E	109.5
N1—C7—H7B	108.2	C12B—C13B—H13F	109.5
C8—C7—H7B	108.2	H13D—C13B—H13F	109.5
C11A—C7—H7B	108.0	H13E—C13B—H13F	109.5
C11B—C7—H7B	108.2	C12B—C14B—H14D	109.5
H7A—C7—H7B	0.2	C12B—C14B—H14E	109.5
O3—C8—O4	125.57 (19)	H14D—C14B—H14E	109.5
O3—C8—C7	124.3 (2)	C12B—C14B—H14F	109.5
O4—C8—C7	110.08 (17)	H14D—C14B—H14F	109.5
O4—C9—C10	107.1 (2)	H14E—C14B—H14F	109.5
O2—S1—N1—C7	−166.24 (16)	C9—O4—C8—O3	0.7 (3)
O1—S1—N1—C7	−37.29 (19)	C9—O4—C8—C7	178.89 (19)
C1—S1—N1—C7	77.88 (18)	N1—C7—C8—O3	−41.0 (3)
O2—S1—C1—C6	150.11 (18)	C11A—C7—C8—O3	79.6 (5)
O1—S1—C1—C6	19.3 (2)	C11B—C7—C8—O3	83.6 (6)
N1—S1—C1—C6	−95.37 (19)	N1—C7—C8—O4	140.70 (18)
O2—S1—C1—C2	−31.1 (2)	C11A—C7—C8—O4	−98.7 (5)
O1—S1—C1—C2	−161.86 (19)	C11B—C7—C8—O4	−94.7 (6)
N1—S1—C1—C2	83.4 (2)	C8—O4—C9—C10	−178.8 (2)
C6—C1—C2—C3	−0.2 (4)	N1—C7—C11A—C12A	−65.9 (7)
S1—C1—C2—C3	−179.0 (2)	C8—C7—C11A—C12A	169.6 (5)
C1—C2—C3—C4	−0.2 (4)	C11B—C7—C11A—C12A	143 (7)
C2—C3—C4—C5	0.2 (4)	C7—C11A—C12A—C14A	−38.3 (10)
C3—C4—C5—C6	0.3 (4)	C7—C11A—C12A—C13A	−163.6 (7)
C2—C1—C6—C5	0.7 (3)	N1—C7—C11B—C12B	−175.5 (10)
S1—C1—C6—C5	179.49 (19)	C8—C7—C11B—C12B	60.3 (13)
C4—C5—C6—C1	−0.7 (4)	C11A—C7—C11B—C12B	−145 (7)
S1—N1—C7—C8	−76.4 (2)	C7—C11B—C12B—C13B	64.6 (14)
S1—N1—C7—C11A	159.2 (4)	C7—C11B—C12B—C14B	−169.4 (10)
S1—N1—C7—C11B	163.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.20	3.032 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.20	3.032 (2)	162

Symmetry code: (i) .