N-Benzyl-N-cyclo­hexyl-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536809048193

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3109

doi:10.1107/S1600536809048193

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N-Benzyl-N-cyclohexyl-4-methylbenzenesulfonamide

Islam Ullah Khan,^a Zeeshan Haider,^a Muhammad Zia-ur-Rehman,^b ^* Muhammad Shafiq ^a and Muhammad Nadeem Arshad ^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 12 November 2009; accepted 13 November 2009; online 18 November 2009)

In the title compound, C₂₀H₂₅NO₂S, the cyclohexyl ring exists in a chair form and the mean plane through all six atoms makes dihedral angles of 56.12 (9) and 55.19 (10)° with the benzene and phenyl rings, respectively. The dihedral angle between the two aromatic rings is 77.23 (7)°. A weak intramolecular C—H⋯O interaction occurs.

Related literature

For the biological activity of sulfonamides, see: Ozbek et al. (2007 ); Parari et al. (2008 ); Ratish et al. (2009 ); Selnam et al. (2001 ). For related structures, see: Khan et al. (2009 ); Zia-ur-Rehman et al. (2009 ); Gowda et al. (2007a ,b ,c ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₂₅NO₂S
M_r = 343.47
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.0702 (4) Å
b = 11.1054 (5) Å
c = 18.1971 (8) Å
V = 1832.96 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.24 × 0.18 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.956, T_max = 0.976
11619 measured reflections
4493 independent reflections
2764 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.097
S = 0.98
4493 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³
Absolute structure: Flack (1983 ), 1915 Friedel pairs
Flack parameter: 0.04 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1	0.98	2.38	2.903 (3)	113

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: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809048193/is2488sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048193/is2488Isup2.hkl

checkCIF report

Comment top

Sulfonamides are well known as anti-inflamatory (Ratish et al., 2009), anti-microbial (Ozbek et al., 2007; Parari et al., 2008), anti HIV (Selnam et al., 2001) compounds. In continuation of our work regarding the synthesis of various sulfur containing heterocycles (Zia-ur-Rehman et al., 2009; Khan et al., 2009), the structure of N-benzyl-N-cyclohexyl-4-methyl benzene sulfonamide, (I), has been determined.

Bond lengths and bond angles of the title molecule (Fig. 1) are almost similar to those in the related molecules (Gowda et al., 2007a,b,c) and are within the normal ranges (Allen et al., 1987). The two aromatic rings as usual are essentially planar, while the cyclohexane ring is in a chair form. The dihedral angles between the two aromatic rings (C1—C6) & (C14—C19), the benzene (C1—C6) ring & the mean plane of cyclohexyl ring (C7—C12), and the phenyl (C14—C19) ring & the mean plane cyclohexyl ring (C7—C12) are 77.23 (7), 56.12 (9) and 55.19 (10)°, respectively, while the r.m.s. deviations for the (C1—C6), (C7—C12) & (C14—C19) rings are 0.0056, 0.2320 and 0.0046 Å, respectively. An intramolecular C—H···O hydrogen bond gives rise to a five membered hydrogen bonded ring (Table 1).

Related literature top

For the biological activity of sulfonamides, see: Ozbek et al. (2007); Parari et al. (2008); Ratish et al. (2009); Selnam et al. (2001). For related structures, see: Khan et al. (2009); Zia-ur-Rehman et al. (2009); Gowda et al. (2007a,b,c). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of N-cyclohexyl-4-methyl benzene sulfonamide (1.089 g, 4.3 mmol), sodium hydride (0.21 g, 0.88 mmol) and N, N-dimethylformamide (10 ml) was stirred at room temperature for half an hour followed by addition of benzyl chloride (1.14 g, 9.0 mmol). Stirring was continued further for a period of three hours and the contents were poured over crushed ice. Precipitated product was isolated, washed and crystallized from a methanol solution.

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: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I), with displacement ellipsoids at the 50% probability level.

N-Benzyl-N-cyclohexyl-4-methylbenzenesulfonamide top

Crystal data top

C₂₀H₂₅NO₂S	F(000) = 736
M_r = 343.47	D_x = 1.245 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2246 reflections
a = 9.0702 (4) Å	θ = 2.9–20.7°
b = 11.1054 (5) Å	µ = 0.19 mm⁻¹
c = 18.1971 (8) Å	T = 296 K
V = 1832.96 (14) Å³	Blocks, yellow
Z = 4	0.24 × 0.18 × 0.13 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4493 independent reflections
Radiation source: fine-focus sealed tube	2764 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.956, T_max = 0.976	k = −14→7
11619 measured reflections	l = −24→22

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0397P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
4493 reflections	Δρ_max = 0.16 e Å⁻³
218 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1915 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (8)

Crystal data top

C₂₀H₂₅NO₂S	V = 1832.96 (14) Å³
M_r = 343.47	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.0702 (4) Å	µ = 0.19 mm⁻¹
b = 11.1054 (5) Å	T = 296 K
c = 18.1971 (8) Å	0.24 × 0.18 × 0.13 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4493 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2764 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.976	R_int = 0.036
11619 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.097	Δρ_max = 0.16 e Å⁻³
S = 0.98	Δρ_min = −0.25 e Å⁻³
4493 reflections	Absolute structure: Flack (1983), 1915 Friedel pairs
218 parameters	Absolute structure parameter: 0.04 (8)
0 restraints

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	0.13668 (7)	0.35270 (6)	0.83512 (3)	0.04431 (17)
O1	0.0611 (2)	0.45762 (15)	0.86060 (9)	0.0603 (5)
O2	0.28860 (18)	0.36124 (17)	0.81433 (9)	0.0604 (5)
N1	0.04730 (19)	0.30283 (17)	0.76418 (9)	0.0396 (5)
C1	0.1256 (3)	0.2456 (2)	0.90607 (11)	0.0386 (5)
C2	0.2185 (3)	0.1481 (2)	0.90729 (13)	0.0520 (6)
H2	0.2872	0.1375	0.8699	0.062*
C3	0.2102 (3)	0.0660 (2)	0.96364 (14)	0.0556 (7)
H3	0.2729	−0.0002	0.9632	0.067*
C4	0.1123 (3)	0.0789 (2)	1.02044 (13)	0.0492 (6)
C5	0.0189 (3)	0.1763 (3)	1.01803 (13)	0.0634 (8)
H5	−0.0498	0.1867	1.0554	0.076*
C6	0.0247 (3)	0.2591 (3)	0.96159 (13)	0.0607 (8)
H6	−0.0399	0.3241	0.9612	0.073*
C7	−0.1161 (2)	0.3031 (2)	0.76700 (11)	0.0404 (6)
H7	−0.1444	0.3559	0.8078	0.049*
C8	−0.1825 (2)	0.1808 (2)	0.78275 (15)	0.0573 (7)
H8A	−0.1451	0.1507	0.8292	0.069*
H8B	−0.1539	0.1246	0.7445	0.069*
C9	−0.3505 (3)	0.1892 (3)	0.78615 (16)	0.0700 (8)
H9A	−0.3916	0.1094	0.7933	0.084*
H9B	−0.3790	0.2385	0.8278	0.084*
C10	−0.4124 (3)	0.2434 (3)	0.71630 (16)	0.0723 (9)
H10A	−0.3913	0.1904	0.6752	0.087*
H10B	−0.5186	0.2508	0.7207	0.087*
C11	−0.3468 (3)	0.3647 (3)	0.70192 (14)	0.0630 (8)
H11A	−0.3752	0.4195	0.7409	0.076*
H11B	−0.3852	0.3961	0.6560	0.076*
C12	−0.1796 (2)	0.3582 (3)	0.69771 (13)	0.0556 (7)
H12A	−0.1509	0.3100	0.6556	0.067*
H12B	−0.1398	0.4385	0.6911	0.067*
C13	0.1222 (3)	0.2229 (2)	0.71193 (11)	0.0423 (6)
H13A	0.0613	0.1522	0.7043	0.051*
H13B	0.2143	0.1964	0.7336	0.051*
C14	0.1544 (2)	0.2793 (2)	0.63832 (12)	0.0412 (6)
C15	0.2396 (3)	0.3820 (2)	0.63277 (14)	0.0582 (8)
H15	0.2745	0.4194	0.6751	0.070*
C16	0.2731 (3)	0.4293 (3)	0.56453 (18)	0.0753 (9)
H16	0.3311	0.4981	0.5614	0.090*
C17	0.2222 (4)	0.3763 (3)	0.50164 (17)	0.0773 (10)
H17	0.2457	0.4082	0.4559	0.093*
C18	0.1365 (4)	0.2759 (3)	0.50727 (15)	0.0756 (9)
H18	0.1007	0.2393	0.4649	0.091*
C19	0.1022 (3)	0.2279 (2)	0.57493 (14)	0.0572 (7)
H19	0.0430	0.1597	0.5777	0.069*
C20	0.1098 (3)	−0.0076 (3)	1.08385 (14)	0.0736 (9)
H20A	0.0270	0.0100	1.1149	0.110*
H20B	0.1993	0.0003	1.1116	0.110*
H20C	0.1015	−0.0884	1.0656	0.110*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0498 (4)	0.0418 (3)	0.0414 (3)	−0.0050 (3)	−0.0074 (3)	−0.0030 (3)
O1	0.0852 (13)	0.0385 (10)	0.0573 (12)	0.0057 (9)	−0.0130 (9)	−0.0102 (9)
O2	0.0487 (10)	0.0769 (14)	0.0555 (11)	−0.0207 (10)	−0.0072 (8)	0.0060 (10)
N1	0.0385 (11)	0.0467 (13)	0.0337 (11)	0.0014 (9)	−0.0024 (8)	−0.0059 (9)
C1	0.0404 (13)	0.0399 (14)	0.0353 (12)	−0.0011 (12)	−0.0071 (11)	−0.0064 (10)
C2	0.0575 (15)	0.0552 (16)	0.0432 (15)	0.0053 (15)	0.0086 (11)	−0.0058 (15)
C3	0.0648 (17)	0.0481 (17)	0.0538 (17)	0.0098 (14)	−0.0022 (14)	−0.0005 (14)
C4	0.0535 (17)	0.0530 (17)	0.0413 (14)	−0.0061 (14)	−0.0065 (13)	0.0013 (12)
C5	0.0583 (17)	0.089 (3)	0.0429 (16)	0.0123 (17)	0.0101 (12)	0.0069 (16)
C6	0.0546 (17)	0.078 (2)	0.0499 (16)	0.0238 (15)	0.0055 (13)	0.0068 (15)
C7	0.0394 (14)	0.0433 (14)	0.0385 (12)	0.0043 (11)	0.0007 (11)	−0.0047 (10)
C8	0.0416 (16)	0.0557 (19)	0.0747 (19)	−0.0022 (12)	0.0023 (12)	0.0114 (15)
C9	0.0506 (16)	0.070 (2)	0.089 (2)	−0.0053 (15)	0.0082 (16)	0.0075 (17)
C10	0.0379 (16)	0.104 (3)	0.075 (2)	0.0028 (16)	−0.0055 (13)	−0.010 (2)
C11	0.0489 (16)	0.084 (2)	0.0561 (16)	0.0138 (17)	−0.0051 (12)	0.0061 (17)
C12	0.0495 (16)	0.0620 (18)	0.0552 (16)	0.0061 (14)	−0.0051 (11)	0.0098 (16)
C13	0.0404 (13)	0.0429 (15)	0.0437 (14)	0.0034 (12)	0.0023 (11)	−0.0019 (11)
C14	0.0426 (14)	0.0415 (15)	0.0396 (13)	0.0057 (12)	0.0020 (11)	−0.0025 (11)
C15	0.0599 (18)	0.062 (2)	0.0528 (16)	−0.0095 (15)	−0.0029 (13)	0.0043 (14)
C16	0.073 (2)	0.078 (2)	0.075 (2)	−0.0156 (18)	0.0113 (18)	0.022 (2)
C17	0.094 (2)	0.090 (3)	0.0482 (19)	0.011 (2)	0.0187 (16)	0.0196 (19)
C18	0.102 (2)	0.079 (2)	0.0459 (17)	0.015 (2)	0.0012 (18)	−0.0021 (16)
C19	0.0699 (19)	0.0531 (18)	0.0486 (16)	0.0012 (14)	0.0012 (13)	−0.0011 (14)
C20	0.093 (2)	0.066 (2)	0.0620 (18)	−0.0067 (18)	−0.0045 (16)	0.0123 (16)

Geometric parameters (Å, º) top

S1—O1	1.4291 (17)	C10—C11	1.495 (4)
S1—O2	1.4321 (17)	C10—H10A	0.9700
S1—N1	1.6219 (18)	C10—H10B	0.9700
S1—C1	1.758 (2)	C11—C12	1.520 (3)
N1—C13	1.467 (3)	C11—H11A	0.9700
N1—C7	1.483 (3)	C11—H11B	0.9700
C1—C6	1.371 (3)	C12—H12A	0.9700
C1—C2	1.372 (3)	C12—H12B	0.9700
C2—C3	1.374 (3)	C13—C14	1.507 (3)
C2—H2	0.9300	C13—H13A	0.9700
C3—C4	1.370 (3)	C13—H13B	0.9700
C3—H3	0.9300	C14—C19	1.372 (3)
C4—C5	1.374 (3)	C14—C15	1.381 (3)
C4—C20	1.502 (3)	C15—C16	1.382 (4)
C5—C6	1.379 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.367 (4)
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.513 (3)	C17—C18	1.364 (4)
C7—C12	1.515 (3)	C17—H17	0.9300
C7—H7	0.9800	C18—C19	1.377 (4)
C8—C9	1.528 (3)	C18—H18	0.9300
C8—H8A	0.9700	C19—H19	0.9300
C8—H8B	0.9700	C20—H20A	0.9600
C9—C10	1.514 (4)	C20—H20B	0.9600
C9—H9A	0.9700	C20—H20C	0.9600
C9—H9B	0.9700

O1—S1—O2	119.55 (12)	C9—C10—H10A	109.5
O1—S1—N1	107.27 (10)	C11—C10—H10B	109.5
O2—S1—N1	107.05 (10)	C9—C10—H10B	109.5
O1—S1—C1	106.61 (10)	H10A—C10—H10B	108.0
O2—S1—C1	107.08 (11)	C10—C11—C12	111.3 (2)
N1—S1—C1	108.96 (10)	C10—C11—H11A	109.4
C13—N1—C7	119.09 (18)	C12—C11—H11A	109.4
C13—N1—S1	119.41 (15)	C10—C11—H11B	109.4
C7—N1—S1	118.11 (14)	C12—C11—H11B	109.4
C6—C1—C2	118.9 (2)	H11A—C11—H11B	108.0
C6—C1—S1	120.3 (2)	C7—C12—C11	110.9 (2)
C2—C1—S1	120.71 (18)	C7—C12—H12A	109.5
C1—C2—C3	120.1 (2)	C11—C12—H12A	109.5
C1—C2—H2	119.9	C7—C12—H12B	109.5
C3—C2—H2	119.9	C11—C12—H12B	109.5
C4—C3—C2	121.9 (2)	H12A—C12—H12B	108.1
C4—C3—H3	119.0	N1—C13—C14	114.46 (18)
C2—C3—H3	119.0	N1—C13—H13A	108.6
C3—C4—C5	117.2 (2)	C14—C13—H13A	108.6
C3—C4—C20	121.5 (3)	N1—C13—H13B	108.6
C5—C4—C20	121.3 (2)	C14—C13—H13B	108.6
C4—C5—C6	121.7 (2)	H13A—C13—H13B	107.6
C4—C5—H5	119.2	C19—C14—C15	118.4 (2)
C6—C5—H5	119.2	C19—C14—C13	120.5 (2)
C1—C6—C5	120.1 (3)	C15—C14—C13	121.1 (2)
C1—C6—H6	120.0	C14—C15—C16	120.2 (3)
C5—C6—H6	120.0	C14—C15—H15	119.9
N1—C7—C8	113.73 (19)	C16—C15—H15	119.9
N1—C7—C12	110.59 (18)	C17—C16—C15	121.0 (3)
C8—C7—C12	111.7 (2)	C17—C16—H16	119.5
N1—C7—H7	106.8	C15—C16—H16	119.5
C8—C7—H7	106.8	C18—C17—C16	118.8 (3)
C12—C7—H7	106.8	C18—C17—H17	120.6
C7—C8—C9	110.4 (2)	C16—C17—H17	120.6
C7—C8—H8A	109.6	C17—C18—C19	120.8 (3)
C9—C8—H8A	109.6	C17—C18—H18	119.6
C7—C8—H8B	109.6	C19—C18—H18	119.6
C9—C8—H8B	109.6	C14—C19—C18	120.9 (3)
H8A—C8—H8B	108.1	C14—C19—H19	119.6
C10—C9—C8	111.1 (2)	C18—C19—H19	119.6
C10—C9—H9A	109.4	C4—C20—H20A	109.5
C8—C9—H9A	109.4	C4—C20—H20B	109.5
C10—C9—H9B	109.4	H20A—C20—H20B	109.5
C8—C9—H9B	109.4	C4—C20—H20C	109.5
H9A—C9—H9B	108.0	H20A—C20—H20C	109.5
C11—C10—C9	110.9 (2)	H20B—C20—H20C	109.5
C11—C10—H10A	109.5

O1—S1—N1—C13	159.58 (16)	S1—N1—C7—C8	−101.8 (2)
O2—S1—N1—C13	30.12 (19)	C13—N1—C7—C12	−69.2 (3)
C1—S1—N1—C13	−85.37 (18)	S1—N1—C7—C12	131.65 (18)
O1—S1—N1—C7	−41.37 (19)	N1—C7—C8—C9	178.9 (2)
O2—S1—N1—C7	−170.83 (17)	C12—C7—C8—C9	−55.1 (3)
C1—S1—N1—C7	73.68 (19)	C7—C8—C9—C10	55.6 (3)
O1—S1—C1—C6	16.6 (2)	C8—C9—C10—C11	−56.8 (3)
O2—S1—C1—C6	145.7 (2)	C9—C10—C11—C12	56.8 (3)
N1—S1—C1—C6	−98.9 (2)	N1—C7—C12—C11	−177.1 (2)
O1—S1—C1—C2	−162.71 (19)	C8—C7—C12—C11	55.2 (3)
O2—S1—C1—C2	−33.6 (2)	C10—C11—C12—C7	−56.0 (3)
N1—S1—C1—C2	81.8 (2)	C7—N1—C13—C14	91.6 (2)
C6—C1—C2—C3	−0.3 (4)	S1—N1—C13—C14	−109.5 (2)
S1—C1—C2—C3	179.01 (18)	N1—C13—C14—C19	−123.0 (2)
C1—C2—C3—C4	−1.0 (4)	N1—C13—C14—C15	58.5 (3)
C2—C3—C4—C5	1.6 (4)	C19—C14—C15—C16	−1.3 (4)
C2—C3—C4—C20	−176.6 (2)	C13—C14—C15—C16	177.2 (2)
C3—C4—C5—C6	−1.0 (4)	C14—C15—C16—C17	0.4 (5)
C20—C4—C5—C6	177.2 (3)	C15—C16—C17—C18	0.4 (5)
C2—C1—C6—C5	0.9 (4)	C16—C17—C18—C19	−0.4 (5)
S1—C1—C6—C5	−178.4 (2)	C15—C14—C19—C18	1.3 (4)
C4—C5—C6—C1	−0.2 (4)	C13—C14—C19—C18	−177.2 (3)
C13—N1—C7—C8	57.3 (3)	C17—C18—C19—C14	−0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.98	2.38	2.903 (3)	113

Experimental details

Crystal data
Chemical formula	C₂₀H₂₅NO₂S
M_r	343.47
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	9.0702 (4), 11.1054 (5), 18.1971 (8)
V (Å³)	1832.96 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.24 × 0.18 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	11619, 4493, 2764
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.097, 0.98
No. of reflections	4493
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25
Absolute structure	Flack (1983), 1915 Friedel pairs
Absolute structure parameter	0.04 (8)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.9800	2.3800	2.903 (3)	113.00

Acknowledgements

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

References

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