N-Cyclo­hexyl-N-ethyl­benzene­sulfonamide

Khan, I.U.; Haider, Z.; Zia-ur-Rehman, M.; Arshad, M.N.; Shafiq, M.

doi:10.1107/S1600536809044006

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2867

https://doi.org/10.1107/S1600536809044006

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N-Cyclohexyl-N-ethylbenzenesulfonamide

Islam Ullah Khan,^a ^* Zeeshan Haider,^a Muhammad Zia-ur-Rehman,^b Muhammad Nadeem Arshad ^a and Muhammad Shafiq ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpure Road, Lahore 54600, Pakistan.
^*Correspondence e-mail: rehman_pcsir@hotmail.com

(Received 22 October 2009; accepted 23 October 2009; online 28 October 2009)

The title compound, C₁₄H₂₁NO₂S, synthesized by N-methylation of cyclohexylamine sulfonamide with ethyl iodide is of interest as a precursor to biologically active sulfur-containing heterocyclic compounds. There are two independent molecules in the asymmetric unit. The dihedral angles between the mean planes of the phenyl ring and the cyclohexyl ring are 40.29 (11) and 37.91 (13)° in the two molecules.

Related literature

For the synthesis of related molecules, see: Arshad et al. (2009 ); Zia-ur-Rehman et al. (2009 ). For the biological activity of sulfonamides, see: Berredjem et al. (2000 ); Lee & Lee (2002 ); Soledade et al. (2006 ); Xiao & Timberlake (2000 ).

Experimental

Crystal data

C₁₄H₂₁NO₂S
M_r = 267.38
Monoclinic, P 2₁ /c
a = 18.195 (1) Å
b = 12.9799 (7) Å
c = 12.7327 (6) Å
β = 108.587 (3)°
V = 2850.2 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.42 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
32427 measured reflections
7061 independent reflections
3979 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.148
S = 0.99
7061 reflections
327 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809044006/bt5111sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044006/bt5111Isup2.hkl

checkCIF report

Comment top

Sulfonamide is an important functionality found in a number of synthetic as well as natural compounds possessing versatile type of biological activities e.g., herbicidal, anti-malarial, anti-convulsant and anti-hypertensive (Soledade et al., 2006; Xiao & Timberlake, 2000; Berredjem et al., 2000; Lee & Lee, 2002) activities.

As a part of our ongoing research program regarding the synthesis of sulfur containing heterocyclic compounds (Arshad et al., 2009; Zia-ur-Rehman et al. 2009), we, herein report the crystal structure of the title compound (Scheme and figure1). Bond lengths and bond angles are within the normal ranges. No significant hydrogen bond interactions are observed in the title molecule. The dihedral angles between the mean planes of the phenyl ring and the cyclohexyl ring are 40.29 (11)° and 37.91 (13)°, respectively, for the two molecules in the asymmetric unit.

Related literature top

For the synthesis of related molecules, see: Arshad et al. (2009); Zia-ur-Rehman et al. (2009). For the biological activity of sulfonamides, see: Berredjem et al. (2000); Lee & Lee (2002); Soledade et al. (2006); Xiao & Timberlake (2000).

Experimental top

A mixture of N-cyclohexylbenzene sulfonamide1(g, 0.43 mmol), sodium hydride (0.21 g; 0.88 mmoles) and N, N-dimethylformamide (10.0 ml) was stirred at room temperature for half an hour followed by addition of ethyl iodide (0.134 g; 0.86 mmoles). Stirring was continued further for a period of three hours and the contents were poured over crushed ice. The precipitated product was isolated, washed and crystallized from a methanol-water mixture (50: 50).

Structure description top

For the synthesis of related molecules, see: Arshad et al. (2009); Zia-ur-Rehman et al. (2009). For the biological activity of sulfonamides, see: Berredjem et al. (2000); Lee & Lee (2002); Soledade et al. (2006); Xiao & Timberlake (2000).

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) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids at the 50% probability level. H atoms have been omitted for clarity.

N-Cyclohexyl-N-ethylbenzenesulfonamide top

Crystal data top

C₁₄H₂₁NO₂S	F(000) = 1152
M_r = 267.38	D_x = 1.246 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3394 reflections
a = 18.195 (1) Å	θ = 2.3–21.8°
b = 12.9799 (7) Å	µ = 0.22 mm⁻¹
c = 12.7327 (6) Å	T = 296 K
β = 108.587 (3)°	Needles, colourless
V = 2850.2 (3) Å³	0.42 × 0.11 × 0.08 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	3979 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.056
Graphite monochromator	θ_max = 28.3°, θ_min = 1.2°
φ and ω scans	h = −24→23
32427 measured reflections	k = −17→16
7061 independent reflections	l = −16→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0572P)² + 0.5289P] where P = (F_o² + 2F_c²)/3
7061 reflections	(Δ/σ)_max < 0.001
327 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₄H₂₁NO₂S	V = 2850.2 (3) Å³
M_r = 267.38	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.195 (1) Å	µ = 0.22 mm⁻¹
b = 12.9799 (7) Å	T = 296 K
c = 12.7327 (6) Å	0.42 × 0.11 × 0.08 mm
β = 108.587 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3979 reflections with I > 2σ(I)
32427 measured reflections	R_int = 0.056
7061 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 0.99	Δρ_max = 0.30 e Å⁻³
7061 reflections	Δρ_min = −0.24 e Å⁻³
327 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.36993 (4)	0.68047 (5)	0.03599 (5)	0.0533 (2)
O1	0.39686 (11)	0.64718 (16)	−0.05209 (14)	0.0755 (6)
O2	0.37154 (11)	0.78735 (14)	0.06200 (17)	0.0710 (6)
N1	0.28139 (11)	0.64066 (15)	0.00768 (15)	0.0464 (5)
C1	0.42614 (14)	0.61647 (19)	0.1568 (2)	0.0473 (6)
C2	0.46699 (15)	0.5285 (2)	0.1493 (2)	0.0574 (7)
H2	0.4652	0.5029	0.0803	0.069*
C3	0.51032 (18)	0.4790 (2)	0.2447 (3)	0.0751 (9)
H3	0.5381	0.4200	0.2401	0.090*
C4	0.5126 (2)	0.5163 (3)	0.3462 (3)	0.0848 (11)
H4	0.5420	0.4826	0.4103	0.102*
C5	0.47221 (19)	0.6025 (3)	0.3537 (2)	0.0793 (10)
H5	0.4737	0.6270	0.4230	0.095*
C6	0.42914 (16)	0.6539 (2)	0.2599 (2)	0.0614 (7)
H6	0.4022	0.7133	0.2657	0.074*
C7	0.23333 (13)	0.68049 (18)	0.07358 (17)	0.0409 (6)
H7	0.2614	0.7389	0.1167	0.049*
C8	0.15687 (14)	0.7218 (2)	−0.00157 (19)	0.0529 (7)
H8A	0.1276	0.6663	−0.0470	0.063*
H8B	0.1666	0.7735	−0.0505	0.063*
C9	0.10942 (16)	0.7692 (2)	0.0651 (2)	0.0637 (8)
H9A	0.1357	0.8302	0.1029	0.076*
H9B	0.0593	0.7902	0.0151	0.076*
C10	0.09773 (17)	0.6946 (2)	0.1492 (2)	0.0725 (9)
H10A	0.0714	0.7294	0.1944	0.087*
H10B	0.0650	0.6383	0.1110	0.087*
C11	0.17359 (17)	0.6522 (2)	0.2226 (2)	0.0701 (8)
H11A	0.1637	0.6011	0.2719	0.084*
H11B	0.2036	0.7074	0.2677	0.084*
C12	0.22025 (15)	0.6035 (2)	0.1559 (2)	0.0572 (7)
H12A	0.1928	0.5439	0.1164	0.069*
H12B	0.2699	0.5805	0.2056	0.069*
C13	0.26176 (16)	0.5405 (2)	−0.0484 (2)	0.0591 (7)
H13A	0.2257	0.5049	−0.0191	0.071*
H13B	0.3084	0.4990	−0.0317	0.071*
C14	0.2265 (2)	0.5491 (3)	−0.1719 (2)	0.0908 (11)
H14A	0.1821	0.5936	−0.1892	0.136*
H14B	0.2109	0.4821	−0.2028	0.136*
H14C	0.2640	0.5773	−0.2026	0.136*
S2	0.14463 (4)	0.28954 (5)	0.47894 (6)	0.0536 (2)
O3	0.12606 (12)	0.31641 (16)	0.57629 (15)	0.0769 (6)
O4	0.13794 (11)	0.18488 (13)	0.44305 (17)	0.0707 (6)
N2	0.23252 (11)	0.32654 (14)	0.49770 (15)	0.0455 (5)
C15	0.08332 (14)	0.36211 (19)	0.3684 (2)	0.0501 (6)
C16	0.07673 (16)	0.3370 (2)	0.2607 (2)	0.0635 (8)
H16	0.1030	0.2803	0.2456	0.076*
C17	0.03073 (18)	0.3967 (3)	0.1753 (3)	0.0799 (9)
H17	0.0267	0.3809	0.1024	0.096*
C18	−0.00889 (18)	0.4787 (3)	0.1970 (3)	0.0850 (10)
H18	−0.0405	0.5181	0.1391	0.102*
C19	−0.00210 (19)	0.5031 (3)	0.3045 (3)	0.0829 (10)
H19	−0.0291	0.5592	0.3192	0.099*
C20	0.04401 (17)	0.4456 (2)	0.3902 (3)	0.0670 (8)
H20	0.0488	0.4628	0.4630	0.080*
C21	0.27320 (13)	0.29122 (17)	0.42041 (17)	0.0398 (6)
H21	0.2384	0.2427	0.3690	0.048*
C22	0.29029 (15)	0.37719 (19)	0.35061 (19)	0.0498 (6)
H22A	0.2425	0.4123	0.3108	0.060*
H22B	0.3250	0.4269	0.3985	0.060*
C23	0.32733 (15)	0.3341 (2)	0.26870 (19)	0.0547 (7)
H23A	0.2902	0.2905	0.2157	0.066*
H23B	0.3408	0.3904	0.2282	0.066*
C24	0.39939 (15)	0.2723 (2)	0.3260 (2)	0.0601 (7)
H24A	0.4185	0.2408	0.2706	0.072*
H24B	0.4393	0.3181	0.3705	0.072*
C25	0.38391 (16)	0.1893 (2)	0.3992 (2)	0.0574 (7)
H25A	0.4324	0.1561	0.4398	0.069*
H25B	0.3501	0.1375	0.3533	0.069*
C26	0.34638 (14)	0.23229 (19)	0.48063 (19)	0.0489 (6)
H26A	0.3338	0.1762	0.5223	0.059*
H26B	0.3826	0.2777	0.5325	0.059*
C27	0.26849 (18)	0.4076 (2)	0.5788 (2)	0.0659 (8)
H27A	0.3243	0.4032	0.5960	0.079*
H27B	0.2567	0.3936	0.6466	0.079*
C28	0.2440 (2)	0.5137 (2)	0.5434 (3)	0.0844 (10)
H28A	0.2526	0.5275	0.4742	0.127*
H28B	0.2736	0.5613	0.5985	0.127*
H28C	0.1899	0.5215	0.5346	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0519 (4)	0.0526 (4)	0.0639 (4)	0.0001 (3)	0.0304 (3)	0.0080 (3)
O1	0.0719 (14)	0.1040 (16)	0.0669 (12)	0.0096 (12)	0.0452 (10)	0.0145 (11)
O2	0.0605 (13)	0.0438 (11)	0.1111 (15)	−0.0072 (10)	0.0307 (11)	0.0086 (10)
N1	0.0459 (13)	0.0466 (13)	0.0501 (11)	−0.0015 (10)	0.0200 (9)	−0.0048 (9)
C1	0.0412 (15)	0.0473 (16)	0.0577 (15)	−0.0071 (13)	0.0218 (12)	−0.0012 (12)
C2	0.0539 (18)	0.0514 (17)	0.0708 (18)	−0.0053 (15)	0.0256 (15)	0.0023 (14)
C3	0.059 (2)	0.062 (2)	0.106 (3)	0.0033 (16)	0.0268 (18)	0.0164 (19)
C4	0.064 (2)	0.096 (3)	0.082 (2)	−0.021 (2)	0.0061 (18)	0.029 (2)
C5	0.072 (2)	0.099 (3)	0.0605 (19)	−0.024 (2)	0.0135 (17)	0.0000 (19)
C6	0.0545 (18)	0.0647 (19)	0.0678 (18)	−0.0144 (15)	0.0236 (15)	−0.0111 (15)
C7	0.0436 (14)	0.0394 (14)	0.0427 (12)	−0.0033 (11)	0.0179 (11)	−0.0017 (10)
C8	0.0531 (16)	0.0558 (17)	0.0501 (13)	0.0040 (14)	0.0168 (12)	0.0076 (12)
C9	0.0546 (18)	0.070 (2)	0.0715 (17)	0.0138 (15)	0.0270 (14)	0.0101 (15)
C10	0.061 (2)	0.086 (2)	0.084 (2)	0.0137 (17)	0.0427 (16)	0.0132 (17)
C11	0.081 (2)	0.079 (2)	0.0640 (17)	0.0060 (18)	0.0433 (16)	0.0147 (15)
C12	0.0603 (18)	0.0580 (17)	0.0589 (15)	0.0040 (15)	0.0268 (13)	0.0149 (13)
C13	0.0666 (19)	0.0513 (17)	0.0613 (16)	0.0017 (14)	0.0228 (14)	−0.0094 (13)
C14	0.109 (3)	0.096 (3)	0.0632 (19)	0.005 (2)	0.0218 (18)	−0.0250 (18)
S2	0.0558 (4)	0.0487 (4)	0.0696 (4)	−0.0011 (3)	0.0386 (3)	0.0054 (3)
O3	0.0871 (15)	0.0920 (15)	0.0755 (12)	0.0103 (12)	0.0596 (11)	0.0152 (11)
O4	0.0642 (13)	0.0413 (11)	0.1158 (15)	−0.0094 (10)	0.0415 (11)	0.0017 (10)
N2	0.0521 (13)	0.0427 (12)	0.0492 (11)	−0.0066 (10)	0.0267 (9)	−0.0077 (9)
C15	0.0408 (15)	0.0497 (16)	0.0676 (16)	−0.0033 (13)	0.0283 (13)	−0.0019 (13)
C16	0.0528 (18)	0.069 (2)	0.0711 (18)	−0.0079 (16)	0.0239 (15)	−0.0120 (16)
C17	0.051 (2)	0.109 (3)	0.071 (2)	−0.010 (2)	0.0067 (16)	0.004 (2)
C18	0.047 (2)	0.083 (3)	0.112 (3)	−0.0060 (19)	0.0077 (19)	0.027 (2)
C19	0.061 (2)	0.067 (2)	0.121 (3)	0.0084 (18)	0.029 (2)	0.000 (2)
C20	0.0582 (19)	0.066 (2)	0.083 (2)	0.0117 (16)	0.0302 (16)	−0.0007 (17)
C21	0.0427 (14)	0.0390 (13)	0.0422 (12)	−0.0044 (11)	0.0197 (10)	−0.0044 (10)
C22	0.0575 (17)	0.0498 (15)	0.0476 (13)	0.0004 (13)	0.0245 (12)	0.0043 (12)
C23	0.0635 (18)	0.0614 (18)	0.0476 (13)	0.0016 (15)	0.0297 (13)	0.0063 (12)
C24	0.0572 (18)	0.0721 (19)	0.0619 (15)	0.0006 (15)	0.0344 (13)	0.0032 (14)
C25	0.0535 (17)	0.0617 (18)	0.0647 (15)	0.0106 (14)	0.0298 (13)	0.0053 (14)
C26	0.0500 (16)	0.0511 (16)	0.0496 (13)	0.0011 (13)	0.0217 (12)	0.0058 (12)
C27	0.085 (2)	0.0609 (19)	0.0617 (16)	−0.0021 (17)	0.0371 (15)	−0.0122 (15)
C28	0.115 (3)	0.060 (2)	0.085 (2)	0.0096 (19)	0.041 (2)	−0.0057 (17)

Geometric parameters (Å, º) top

S1—O2	1.4244 (19)	S2—O4	1.4261 (18)
S1—O1	1.4266 (18)	S2—O3	1.4280 (17)
S1—N1	1.619 (2)	S2—N2	1.613 (2)
S1—C1	1.761 (3)	S2—C15	1.764 (3)
N1—C13	1.472 (3)	N2—C27	1.473 (3)
N1—C7	1.485 (3)	N2—C21	1.480 (3)
C1—C2	1.382 (3)	C15—C20	1.375 (4)
C1—C6	1.384 (3)	C15—C16	1.377 (3)
C2—C3	1.378 (4)	C16—C17	1.379 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.368 (4)	C17—C18	1.363 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.359 (5)	C18—C19	1.371 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.374 (4)	C19—C20	1.367 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.513 (3)	C21—C26	1.515 (3)
C7—C12	1.520 (3)	C21—C22	1.519 (3)
C7—H7	0.9800	C21—H21	0.9800
C8—C9	1.520 (3)	C22—C23	1.517 (3)
C8—H8A	0.9700	C22—H22A	0.9700
C8—H8B	0.9700	C22—H22B	0.9700
C9—C10	1.508 (4)	C23—C24	1.512 (4)
C9—H9A	0.9700	C23—H23A	0.9700
C9—H9B	0.9700	C23—H23B	0.9700
C10—C11	1.503 (4)	C24—C25	1.508 (3)
C10—H10A	0.9700	C24—H24A	0.9700
C10—H10B	0.9700	C24—H24B	0.9700
C11—C12	1.517 (3)	C25—C26	1.519 (3)
C11—H11A	0.9700	C25—H25A	0.9700
C11—H11B	0.9700	C25—H25B	0.9700
C12—H12A	0.9700	C26—H26A	0.9700
C12—H12B	0.9700	C26—H26B	0.9700
C13—C14	1.501 (4)	C27—C28	1.474 (4)
C13—H13A	0.9700	C27—H27A	0.9700
C13—H13B	0.9700	C27—H27B	0.9700
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600

O2—S1—O1	119.41 (12)	O4—S2—O3	119.41 (12)
O2—S1—N1	107.93 (11)	O4—S2—N2	108.09 (11)
O1—S1—N1	107.15 (11)	O3—S2—N2	107.24 (11)
O2—S1—C1	107.05 (12)	O4—S2—C15	106.58 (12)
O1—S1—C1	107.14 (12)	O3—S2—C15	107.33 (12)
N1—S1—C1	107.67 (11)	N2—S2—C15	107.70 (11)
C13—N1—C7	119.10 (19)	C27—N2—C21	118.87 (19)
C13—N1—S1	117.41 (17)	C27—N2—S2	120.95 (16)
C7—N1—S1	119.11 (15)	C21—N2—S2	119.45 (15)
C2—C1—C6	119.8 (2)	C20—C15—C16	120.2 (3)
C2—C1—S1	120.3 (2)	C20—C15—S2	119.8 (2)
C6—C1—S1	120.0 (2)	C16—C15—S2	120.0 (2)
C3—C2—C1	119.5 (3)	C15—C16—C17	119.4 (3)
C3—C2—H2	120.3	C15—C16—H16	120.3
C1—C2—H2	120.3	C17—C16—H16	120.3
C4—C3—C2	120.3 (3)	C18—C17—C16	120.4 (3)
C4—C3—H3	119.8	C18—C17—H17	119.8
C2—C3—H3	119.8	C16—C17—H17	119.8
C5—C4—C3	120.2 (3)	C17—C18—C19	119.9 (3)
C5—C4—H4	119.9	C17—C18—H18	120.1
C3—C4—H4	119.9	C19—C18—H18	120.1
C4—C5—C6	120.7 (3)	C20—C19—C18	120.5 (3)
C4—C5—H5	119.7	C20—C19—H19	119.7
C6—C5—H5	119.7	C18—C19—H19	119.7
C5—C6—C1	119.5 (3)	C19—C20—C15	119.7 (3)
C5—C6—H6	120.2	C19—C20—H20	120.2
C1—C6—H6	120.2	C15—C20—H20	120.2
N1—C7—C8	110.77 (18)	N2—C21—C26	111.41 (18)
N1—C7—C12	114.24 (19)	N2—C21—C22	113.61 (19)
C8—C7—C12	110.8 (2)	C26—C21—C22	110.87 (19)
N1—C7—H7	106.9	N2—C21—H21	106.8
C8—C7—H7	106.9	C26—C21—H21	106.8
C12—C7—H7	106.9	C22—C21—H21	106.8
C7—C8—C9	111.2 (2)	C23—C22—C21	110.5 (2)
C7—C8—H8A	109.4	C23—C22—H22A	109.6
C9—C8—H8A	109.4	C21—C22—H22A	109.6
C7—C8—H8B	109.4	C23—C22—H22B	109.6
C9—C8—H8B	109.4	C21—C22—H22B	109.6
H8A—C8—H8B	108.0	H22A—C22—H22B	108.1
C10—C9—C8	111.7 (2)	C24—C23—C22	111.8 (2)
C10—C9—H9A	109.3	C24—C23—H23A	109.3
C8—C9—H9A	109.3	C22—C23—H23A	109.3
C10—C9—H9B	109.3	C24—C23—H23B	109.3
C8—C9—H9B	109.3	C22—C23—H23B	109.3
H9A—C9—H9B	107.9	H23A—C23—H23B	107.9
C11—C10—C9	111.5 (2)	C25—C24—C23	111.9 (2)
C11—C10—H10A	109.3	C25—C24—H24A	109.2
C9—C10—H10A	109.3	C23—C24—H24A	109.2
C11—C10—H10B	109.3	C25—C24—H24B	109.2
C9—C10—H10B	109.3	C23—C24—H24B	109.2
H10A—C10—H10B	108.0	H24A—C24—H24B	107.9
C10—C11—C12	111.8 (2)	C24—C25—C26	111.9 (2)
C10—C11—H11A	109.3	C24—C25—H25A	109.2
C12—C11—H11A	109.3	C26—C25—H25A	109.2
C10—C11—H11B	109.3	C24—C25—H25B	109.2
C12—C11—H11B	109.3	C26—C25—H25B	109.2
H11A—C11—H11B	107.9	H25A—C25—H25B	107.9
C11—C12—C7	110.5 (2)	C21—C26—C25	110.73 (19)
C11—C12—H12A	109.5	C21—C26—H26A	109.5
C7—C12—H12A	109.5	C25—C26—H26A	109.5
C11—C12—H12B	109.5	C21—C26—H26B	109.5
C7—C12—H12B	109.5	C25—C26—H26B	109.5
H12A—C12—H12B	108.1	H26A—C26—H26B	108.1
N1—C13—C14	113.5 (2)	N2—C27—C28	115.4 (2)
N1—C13—H13A	108.9	N2—C27—H27A	108.4
C14—C13—H13A	108.9	C28—C27—H27A	108.4
N1—C13—H13B	108.9	N2—C27—H27B	108.4
C14—C13—H13B	108.9	C28—C27—H27B	108.4
H13A—C13—H13B	107.7	H27A—C27—H27B	107.5
C13—C14—H14A	109.5	C27—C28—H28A	109.5
C13—C14—H14B	109.5	C27—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C13—C14—H14C	109.5	C27—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5

O2—S1—N1—C13	164.91 (17)	O4—S2—N2—C27	−151.80 (18)
O1—S1—N1—C13	35.1 (2)	O3—S2—N2—C27	−21.8 (2)
C1—S1—N1—C13	−79.84 (19)	C15—S2—N2—C27	93.4 (2)
O2—S1—N1—C7	−38.8 (2)	O4—S2—N2—C21	38.1 (2)
O1—S1—N1—C7	−168.55 (16)	O3—S2—N2—C21	168.11 (17)
C1—S1—N1—C7	76.49 (19)	C15—S2—N2—C21	−76.65 (19)
O2—S1—C1—C2	−148.1 (2)	O4—S2—C15—C20	144.5 (2)
O1—S1—C1—C2	−18.9 (2)	O3—S2—C15—C20	15.5 (2)
N1—S1—C1—C2	96.0 (2)	N2—S2—C15—C20	−99.7 (2)
O2—S1—C1—C6	32.3 (2)	O4—S2—C15—C16	−37.5 (2)
O1—S1—C1—C6	161.5 (2)	O3—S2—C15—C16	−166.5 (2)
N1—S1—C1—C6	−83.5 (2)	N2—S2—C15—C16	78.3 (2)
C6—C1—C2—C3	0.0 (4)	C20—C15—C16—C17	0.4 (4)
S1—C1—C2—C3	−179.6 (2)	S2—C15—C16—C17	−177.7 (2)
C1—C2—C3—C4	0.4 (4)	C15—C16—C17—C18	−1.1 (4)
C2—C3—C4—C5	0.0 (5)	C16—C17—C18—C19	1.0 (5)
C3—C4—C5—C6	−0.6 (5)	C17—C18—C19—C20	−0.2 (5)
C4—C5—C6—C1	0.9 (4)	C18—C19—C20—C15	−0.6 (5)
C2—C1—C6—C5	−0.6 (4)	C16—C15—C20—C19	0.5 (4)
S1—C1—C6—C5	179.0 (2)	S2—C15—C20—C19	178.5 (2)
C13—N1—C7—C8	−76.0 (3)	C27—N2—C21—C26	68.9 (3)
S1—N1—C7—C8	128.08 (19)	S2—N2—C21—C26	−120.80 (19)
C13—N1—C7—C12	49.9 (3)	C27—N2—C21—C22	−57.1 (3)
S1—N1—C7—C12	−106.0 (2)	S2—N2—C21—C22	113.1 (2)
N1—C7—C8—C9	−176.3 (2)	N2—C21—C22—C23	−176.43 (19)
C12—C7—C8—C9	55.9 (3)	C26—C21—C22—C23	57.2 (3)
C7—C8—C9—C10	−54.6 (3)	C21—C22—C23—C24	−55.4 (3)
C8—C9—C10—C11	53.9 (3)	C22—C23—C24—C25	53.6 (3)
C9—C10—C11—C12	−54.9 (3)	C23—C24—C25—C26	−53.3 (3)
C10—C11—C12—C7	56.1 (3)	N2—C21—C26—C25	175.45 (19)
N1—C7—C12—C11	177.6 (2)	C22—C21—C26—C25	−57.0 (3)
C8—C7—C12—C11	−56.5 (3)	C24—C25—C26—C21	55.0 (3)
C7—N1—C13—C14	107.4 (3)	C21—N2—C27—C28	93.3 (3)
S1—N1—C13—C14	−96.2 (3)	S2—N2—C27—C28	−76.8 (3)

Experimental details

Crystal data
Chemical formula	C₁₄H₂₁NO₂S
M_r	267.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.195 (1), 12.9799 (7), 12.7327 (6)
β (°)	108.587 (3)
V (Å³)	2850.2 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.42 × 0.11 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	32427, 7061, 3979
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.148, 0.99
No. of reflections	7061
No. of parameters	327
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008) and local programs.

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

Arshad, M. N., Zia-ur-Rehman, M. & Khan, I. U. (2009). Acta Cryst. E65, o2596. Web of Science CSD CrossRef IUCr Journals Google Scholar
Berredjem, M., Régainia, Z., Djahoudi, A., Aouf, N. E., Dewinter, G. & Montero, J. L. (2000). Phosphorus Sulfur Silicon Relat. Elem. 165, 249–264. Web of Science CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lee, J. S. & Lee, C. H. (2002). Bull. Korean Chem. Soc. 23, 167–169. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soledade, M., Pedras, C. & Jha, M. (2006). Bioorg. Med. Chem. 14, 4958–4979. Web of Science PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xiao, Z. & Timberlake, J. W. (2000). J. Heterocycl. Chem. 37, 773–777. CrossRef CAS Google Scholar
Zia-ur-Rehman, M., Choudary, J. A., Elsegood, M. R. J., Siddiqui, H. L. & Khan, K. M. (2009). Eur. J. Med. Chem. 44, 1311–1316. Web of Science PubMed CAS Google Scholar