Ethyl 2-benzene­sulfonamido-4-methyl­penta­noate

Arshad, M.N.; Danish, M.; Tahir, M.N.; Khalid, S.; Asiri, A.M.

doi:10.1107/S1600536812037658

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2874

https://doi.org/10.1107/S1600536812037658

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Ethyl 2-benzenesulfonamido-4-methylpentanoate

Muhammad Nadeem Arshad,^a ^* Muhammad Danish,^b ^* Muhammad Nawaz Tahir,^c Savera Khalid ^b and Abdullah M. Asiri ^d,^a

^aCenter of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bDepartment of Chemistry, University of Gujrat, Gujrat 50700, Pakistan, ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia
^*Correspondence e-mail: mnachemist@hotmail.com, drdanish62@gmail.com

(Received 6 August 2012; accepted 1 September 2012; online 8 September 2012)

In the title compound, C₁₄H₂₁NO₄S, the O—S—O angle is 120.06 (11)°, with the S atom adopting a distorted tetrahedral geometry. In the crystal, N—H⋯O hydrogen bonds connect the molecules 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_r = 299.38
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.098
S = 1.04
3081 reflections
223 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1220 Friedel pairs
Flack parameter: 0.01 (9)

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) x+1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812037658/bt5998sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037658/bt5998Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037658/bt5998Isup3.cml

checkCIF report

Comment top

We report the crystal structure of title compound in continuation to our work on synthesis of sulfonamide derived from amino acids (Arshad et al., 2010; Arshad et al., 2012).

The methylester moiety (C7/C8/O3/O4/C9/C10) is almost planer with r. m. s. deviation of 0.0113 (2) Å and is oriented at dihedral angle of 21.37 (13)° with respect to the aromatic ring (C1—C6). The S atom adopts a distorted tetrahedral geometry and the bond angles are in comparison with the already published compound 4-methyl-2- (2-nitrobenzenesulfonamido)pentanoic acid (Arshad et al., 2012). The crystal structure shows intermolecular N—H···O hydrogen bonds connecting the molecules to a chain running along the a axis (Table. 1, Fig. 2). The isobutyl group is disordered over two positions with occupancies of 0.504 (3):0.496 (3) for (C11A—C14A) & (C11B—C14B) respectively.

Related literature top

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

Experimental top

4-Methyl-2-[(phenylsulfonyl)amino]pentanoic acid (0.20 g, 0.738 mmol) added to the mixture of NaH (0.035g, 1.47 mmol) in dimethylformamide (5 mL). The mixture was stirred for 15 mins followed by addition of ethyliodide (0.135 g, 0.86 mmol). Stirring was continued for 3-4 h and then mixture was poured on ice, precipitate obtained was filtered off, washed with water and recrystalized in ethylacetate under slow evaporation to give yellow crystal.

Structure description top

We report the crystal structure of title compound in continuation to our work on synthesis of sulfonamide derived from amino acids (Arshad et al., 2010; Arshad et al., 2012).

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. The labelled molecular structure of (I) with 50% displacement ellipsoids.
	Fig. 2. Unit cell packing showing hydrogen bonds, drawn using dashed lines.

Ethyl 2-benzenesulfonamido-4-methylpentanoate top

Crystal data top

C₁₄H₂₁NO₄S	F(000) = 640
M_r = 299.38	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0506P)² + 0.2498P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3081 reflections	Δρ_max = 0.17 e Å⁻³
223 parameters	Δρ_min = −0.23 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 1220 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (9)

Crystal data top

C₁₄H₂₁NO₄S	V = 1587.66 (19) Å³
M_r = 299.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.3084 (3) Å	µ = 0.22 mm⁻¹
b = 9.5507 (7) Å	T = 296 K
c = 31.315 (2) Å	0.41 × 0.37 × 0.34 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3081 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2701 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.930	R_int = 0.024
12652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	Δρ_max = 0.17 e Å⁻³
S = 1.04	Δρ_min = −0.23 e Å⁻³
3081 reflections	Absolute structure: Flack (1983), 1220 Friedel pairs
223 parameters	Absolute structure parameter: 0.01 (9)
4 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₁NO₄S
M_r	299.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.3084 (3), 9.5507 (7), 31.315 (2)
V (Å³)	1587.66 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.41 × 0.37 × 0.34

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.917, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	12652, 3081, 2701
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.098, 1.04
No. of reflections	3081
No. of parameters	223
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.23
Absolute structure	Flack (1983), 1220 Friedel pairs
Absolute structure parameter	0.01 (9)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), WinGX (Farrugia, 1999) and X-SEED (Barbour, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.20	3.032 (2)	162.1

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors acknowledge the University of Sargodha, Pakistan, for providing diffraction facilities at the Department of Physics.

References

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