(2-Methyl-1-phenyl­sulfonyl-1H-indol-3-yl)phenyl­methyl acetate

Saravanan, B.; Dhayalan, V.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536809044365

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2906

https://doi.org/10.1107/S1600536809044365

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(2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)phenylmethyl acetate

B. Saravanan,^a V. Dhayalan,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c and V. Manivannan ^a ^*

^aDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 22 October 2009; accepted 25 October 2009; online 28 October 2009)

In the title compound, C₂₄H₂₁NO₄S, the indole ring system makes dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the S- and C-bound phenyl rings. The molecular structure is stabilized by a weak intramolecular C—H⋯O hydrogen bond. In the crystal, a weak intermolecular C—H⋯O hydrogen bond and a C—H⋯π interaction are also observed.

Related literature

For the biological activity of indole derivatives, see: Chai et al. (2006 ); Olgen & Coban (2003 ). For related structures, see: Chakkaravarthi et al. (2007 , 2008 ).

Experimental

Crystal data

C₂₄H₂₁NO₄S
M_r = 419.48
Monoclinic, P 2₁ /n
a = 14.3655 (6) Å
b = 8.3432 (4) Å
c = 18.6261 (8) Å
β = 108.086 (2)°
V = 2122.12 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 295 K
0.28 × 0.24 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.951, T_max = 0.968
23327 measured reflections
4712 independent reflections
3030 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.146
S = 1.01
4712 reflections
273 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.39	2.977 (4)	121
C24—H24B⋯O2ⁱ	0.96	2.58	3.429 (4)	147
C15—H15A⋯Cg1ⁱⁱ	0.96	2.97	3.590 (3)	124
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x, -y, -z+1. Cg1 is the centroid of the C17–C22 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809044365/is2478sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044365/is2478Isup2.hkl

checkCIF report

Comment top

In continuation of our studies of indole derivatives, which are known to exhibit antihepatitis B virus (Chai et al., 2006) and anti-oxidant activity (Olgen & Coban, 2003), we report the crystal structure of the title compound, (I). The bond lengths and bond angles of the title compound are agree with the reported similar structures (Chakkaravarthi et al., 2007,2008).

The phenyl rings C1—C6 and C17—C22 make dihedral angles of 77.8 (1) and 85.4 (1)°, respectively, with the indole ring system. The two phenyl rings are inclined at an angle of 62.2 (1)° with respect to each other. The torsion angles C7—N1—S1—O2 and C14—N1—S1—O1 [-36.8 (2) and 51.1 (2)°, respectively] indicate a syn conformation of the sulfonyl moiety. The sum of the bond angles around N1 [351.2 (2)°] indicates that N1 is sp²-hybridized.

The molecular structure is controlled by a weak intramolecular C—H···O hydrogen bond and the crystal packing of (I) (Fig. 2) is through weak intermolecular C—H···O hydrogen bonds and C—H···π (Table 1) interactions.

Related literature top

For the biological activity of indole derivatives, see: Chai et al. (2006); Olgen & Coban (2003). For related structures, see: Chakkaravarthi et al. (2007, 2008). Cg1 is the centroid of the C17–C22 ring.

Experimental top

To a solution of 1-phenylsulfonyl-(2-methyl-1H-indol-3-yl) (phenyl)methanol (0.5 g, 1.32 mmol) in dry DCM (20 ml) acetic anhydride (0.27 g, 2.64 mmol) and pyridine (0.2 g, 2.52 mmol) were added. It was then stirred at room temperature for 7 h under N₂ atmosphere. The reaction mixture was poured over crushed ice (100 g) containing 2 ml of Conc. HCl, extracted with CHCl₃ (3 × 10 ml) and dried (Na₂SO₄). Removal of solvent followed by recrystallization from CDCl₃ afforded the compound as crystals.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

(2-Methyl-1-phenylsulfonyl-1H-indol-3-yl)phenylmethyl acetate top

Crystal data top

C₂₄H₂₁NO₄S	F(000) = 880
M_r = 419.48	D_x = 1.313 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6715 reflections
a = 14.3655 (6) Å	θ = 2.3–25.3°
b = 8.3432 (4) Å	µ = 0.18 mm⁻¹
c = 18.6261 (8) Å	T = 295 K
β = 108.086 (2)°	Block, colourless
V = 2122.12 (16) Å³	0.28 × 0.24 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	4712 independent reflections
Radiation source: fine-focus sealed tube	3030 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω and φ scans	θ_max = 27.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
T_min = 0.951, T_max = 0.968	k = −9→10
23327 measured reflections	l = −23→24

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0657P)² + 0.817P] where P = (F_o² + 2F_c²)/3
4712 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.26 e Å⁻³
2 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₄H₂₁NO₄S	V = 2122.12 (16) Å³
M_r = 419.48	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.3655 (6) Å	µ = 0.18 mm⁻¹
b = 8.3432 (4) Å	T = 295 K
c = 18.6261 (8) Å	0.28 × 0.24 × 0.18 mm
β = 108.086 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4712 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3030 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.968	R_int = 0.043
23327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	Δρ_max = 0.26 e Å⁻³
4712 reflections	Δρ_min = −0.35 e Å⁻³
273 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.39968 (15)	0.2073 (3)	0.58199 (12)	0.0515 (5)
C2	0.49717 (19)	0.1911 (4)	0.58978 (19)	0.0807 (8)
H2	0.5361	0.2802	0.5897	0.097*
C3	0.5362 (2)	0.0363 (4)	0.5978 (2)	0.0976 (10)
H3	0.6024	0.0216	0.6039	0.117*
C4	0.4786 (2)	−0.0927 (4)	0.59684 (17)	0.0836 (8)
H4	0.5056	−0.1949	0.6014	0.100*
C5	0.3827 (2)	−0.0755 (3)	0.58934 (16)	0.0741 (7)
H5	0.3439	−0.1652	0.5885	0.089*
C6	0.34286 (18)	0.0747 (3)	0.58297 (14)	0.0645 (7)
H6	0.2772	0.0875	0.5793	0.077*
C7	0.15867 (14)	0.3154 (3)	0.49542 (11)	0.0430 (5)
C8	0.11839 (14)	0.2508 (2)	0.42695 (11)	0.0416 (5)
C9	0.18128 (14)	0.2795 (3)	0.38139 (11)	0.0448 (5)
C10	0.17326 (19)	0.2446 (3)	0.30680 (13)	0.0623 (6)
H10	0.1193	0.1894	0.2762	0.075*
C11	0.2471 (2)	0.2937 (4)	0.27933 (16)	0.0780 (8)
H11	0.2429	0.2711	0.2295	0.094*
C12	0.3271 (2)	0.3760 (4)	0.32454 (18)	0.0768 (8)
H12	0.3758	0.4084	0.3044	0.092*
C13	0.33684 (17)	0.4113 (3)	0.39800 (16)	0.0624 (7)
H13	0.3913	0.4662	0.4283	0.075*
C14	0.26243 (14)	0.3622 (2)	0.42576 (12)	0.0450 (5)
C15	0.11753 (18)	0.3291 (4)	0.55899 (14)	0.0671 (7)
H15A	0.0505	0.2942	0.5427	0.101*
H15B	0.1207	0.4388	0.5752	0.101*
H15C	0.1547	0.2633	0.6002	0.101*
C16	0.02422 (14)	0.1601 (3)	0.40188 (11)	0.0441 (5)
H16	−0.0023	0.1524	0.4443	0.053*
C17	0.03687 (14)	−0.0071 (3)	0.37520 (12)	0.0462 (5)
C18	0.10644 (19)	−0.1056 (3)	0.42217 (16)	0.0698 (7)
H18	0.1445	−0.0681	0.4691	0.084*
C19	0.1201 (2)	−0.2590 (4)	0.4002 (2)	0.0888 (10)
H19	0.1675	−0.3240	0.4324	0.107*
C20	0.0652 (3)	−0.3164 (4)	0.3322 (2)	0.0871 (9)
H20	0.0751	−0.4199	0.3175	0.105*
C21	−0.0047 (2)	−0.2208 (4)	0.28573 (17)	0.0763 (8)
H21	−0.0434	−0.2600	0.2393	0.092*
C22	−0.01860 (17)	−0.0670 (3)	0.30661 (13)	0.0570 (6)
H22	−0.0661	−0.0028	0.2740	0.068*
C23	−0.13810 (17)	0.2461 (4)	0.33675 (15)	0.0638 (7)
C24	−0.1970 (2)	0.3458 (4)	0.27301 (16)	0.0905 (10)
H24A	−0.2652	0.3353	0.2684	0.136*
H24B	−0.1863	0.3107	0.2271	0.136*
H24C	−0.1777	0.4559	0.2822	0.136*
N1	0.24997 (11)	0.3880 (2)	0.49744 (10)	0.0460 (4)
O1	0.41254 (12)	0.5105 (2)	0.55926 (11)	0.0776 (6)
O2	0.31180 (12)	0.4240 (2)	0.63643 (10)	0.0722 (5)
O3	−0.04306 (10)	0.25213 (18)	0.34207 (8)	0.0521 (4)
O4	−0.16788 (13)	0.1681 (4)	0.37807 (14)	0.1077 (8)
S1	0.34717 (4)	0.39792 (7)	0.57453 (3)	0.0550 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0450 (12)	0.0497 (13)	0.0509 (12)	0.0019 (10)	0.0020 (9)	0.0002 (10)
C2	0.0482 (14)	0.0716 (19)	0.117 (2)	0.0010 (13)	0.0178 (15)	0.0069 (16)
C3	0.0590 (17)	0.089 (2)	0.143 (3)	0.0230 (13)	0.0295 (18)	0.018 (2)
C4	0.091 (2)	0.0648 (18)	0.093 (2)	0.0246 (12)	0.0245 (17)	0.0178 (15)
C5	0.0770 (18)	0.0534 (16)	0.0851 (19)	0.0061 (13)	0.0152 (15)	0.0120 (13)
C6	0.0546 (14)	0.0528 (15)	0.0786 (17)	0.0003 (11)	0.0098 (12)	0.0062 (12)
C7	0.0348 (10)	0.0437 (12)	0.0481 (11)	0.0009 (8)	0.0095 (8)	−0.0012 (9)
C8	0.0350 (10)	0.0425 (11)	0.0461 (11)	0.0017 (8)	0.0110 (8)	0.0030 (8)
C9	0.0403 (11)	0.0432 (12)	0.0510 (12)	0.0054 (9)	0.0142 (9)	0.0070 (9)
C10	0.0609 (14)	0.0761 (18)	0.0529 (13)	0.0012 (12)	0.0222 (11)	0.0023 (12)
C11	0.0809 (19)	0.101 (2)	0.0631 (15)	0.0118 (17)	0.0387 (15)	0.0146 (15)
C12	0.0630 (17)	0.089 (2)	0.093 (2)	0.0123 (15)	0.0453 (16)	0.0327 (17)
C13	0.0435 (12)	0.0586 (16)	0.0878 (18)	0.0013 (10)	0.0243 (12)	0.0209 (13)
C14	0.0359 (10)	0.0392 (12)	0.0596 (13)	0.0060 (8)	0.0146 (9)	0.0117 (9)
C15	0.0537 (14)	0.091 (2)	0.0574 (14)	−0.0115 (13)	0.0185 (11)	−0.0183 (13)
C16	0.0354 (10)	0.0514 (13)	0.0408 (10)	−0.0007 (9)	0.0050 (8)	0.0027 (9)
C17	0.0374 (10)	0.0471 (13)	0.0515 (12)	−0.0045 (9)	0.0102 (9)	0.0053 (9)
C18	0.0609 (15)	0.0552 (16)	0.0789 (17)	0.0024 (12)	0.0009 (13)	0.0109 (13)
C19	0.082 (2)	0.0535 (18)	0.121 (3)	0.0137 (15)	0.0171 (19)	0.0200 (17)
C20	0.103 (2)	0.0510 (17)	0.120 (3)	0.0054 (17)	0.052 (2)	−0.0065 (17)
C21	0.089 (2)	0.0676 (19)	0.0777 (18)	−0.0066 (16)	0.0334 (16)	−0.0204 (15)
C22	0.0571 (13)	0.0588 (15)	0.0527 (13)	0.0017 (11)	0.0135 (11)	−0.0047 (11)
C23	0.0402 (12)	0.0856 (19)	0.0601 (14)	0.0121 (12)	0.0077 (11)	−0.0171 (13)
C24	0.0653 (17)	0.114 (3)	0.0726 (17)	0.0443 (17)	−0.0071 (14)	−0.0203 (16)
N1	0.0352 (9)	0.0430 (10)	0.0556 (10)	−0.0032 (7)	0.0082 (7)	−0.0001 (8)
O1	0.0533 (10)	0.0505 (11)	0.1134 (15)	−0.0194 (8)	0.0033 (9)	−0.0008 (10)
O2	0.0649 (10)	0.0761 (12)	0.0635 (9)	0.0035 (9)	0.0021 (7)	−0.0289 (9)
O3	0.0376 (8)	0.0569 (10)	0.0549 (9)	0.0070 (6)	0.0041 (6)	0.0029 (7)
O4	0.0438 (10)	0.180 (3)	0.1018 (16)	0.0050 (13)	0.0256 (11)	0.0205 (17)
S1	0.0428 (3)	0.0439 (3)	0.0671 (4)	−0.0055 (2)	0.0009 (2)	−0.0092 (3)

Geometric parameters (Å, º) top

C1—C2	1.369 (3)	C14—N1	1.418 (3)
C1—C6	1.378 (3)	C15—H15A	0.9600
C1—S1	1.747 (2)	C15—H15B	0.9600
C2—C3	1.398 (4)	C15—H15C	0.9600
C2—H2	0.9300	C16—O3	1.448 (2)
C3—C4	1.354 (5)	C16—C17	1.510 (3)
C3—H3	0.9300	C16—H16	0.9800
C4—C5	1.349 (4)	C17—C22	1.373 (3)
C4—H4	0.9300	C17—C18	1.377 (3)
C5—C6	1.368 (4)	C18—C19	1.376 (4)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.354 (5)
C7—C8	1.339 (3)	C19—H19	0.9300
C7—N1	1.434 (3)	C20—C21	1.362 (4)
C7—C15	1.483 (3)	C20—H20	0.9300
C8—C9	1.438 (3)	C21—C22	1.373 (4)
C8—C16	1.493 (3)	C21—H21	0.9300
C9—C14	1.386 (3)	C22—H22	0.9300
C9—C10	1.389 (3)	C23—O4	1.184 (3)
C10—C11	1.375 (4)	C23—O3	1.339 (3)
C10—H10	0.9300	C23—C24	1.481 (4)
C11—C12	1.379 (4)	C24—H24A	0.9600
C11—H11	0.9300	C24—H24B	0.9600
C12—C13	1.364 (4)	C24—H24C	0.9600
C12—H12	0.9300	N1—S1	1.6653 (17)
C13—C14	1.386 (3)	O1—S1	1.4181 (18)
C13—H13	0.9300	O2—S1	1.4137 (19)

C2—C1—C6	120.7 (2)	H15A—C15—H15C	109.5
C2—C1—S1	120.0 (2)	H15B—C15—H15C	109.5
C6—C1—S1	119.25 (18)	O3—C16—C8	107.17 (17)
C1—C2—C3	117.7 (3)	O3—C16—C17	110.88 (16)
C1—C2—H2	121.1	C8—C16—C17	112.41 (17)
C3—C2—H2	121.1	O3—C16—H16	108.8
C4—C3—C2	120.7 (3)	C8—C16—H16	108.8
C4—C3—H3	119.7	C17—C16—H16	108.8
C2—C3—H3	119.7	C22—C17—C18	118.1 (2)
C5—C4—C3	121.1 (3)	C22—C17—C16	123.24 (19)
C5—C4—H4	119.4	C18—C17—C16	118.7 (2)
C3—C4—H4	119.4	C19—C18—C17	120.5 (3)
C4—C5—C6	119.5 (3)	C19—C18—H18	119.7
C4—C5—H5	120.2	C17—C18—H18	119.7
C6—C5—H5	120.2	C20—C19—C18	120.8 (3)
C5—C6—C1	120.2 (2)	C20—C19—H19	119.6
C5—C6—H6	119.9	C18—C19—H19	119.6
C1—C6—H6	119.9	C19—C20—C21	119.2 (3)
C8—C7—N1	108.42 (17)	C19—C20—H20	120.4
C8—C7—C15	129.05 (19)	C21—C20—H20	120.4
N1—C7—C15	122.29 (18)	C20—C21—C22	120.7 (3)
C7—C8—C9	109.27 (18)	C20—C21—H21	119.6
C7—C8—C16	125.70 (18)	C22—C21—H21	119.6
C9—C8—C16	125.02 (18)	C21—C22—C17	120.7 (2)
C14—C9—C10	119.6 (2)	C21—C22—H22	119.6
C14—C9—C8	107.29 (18)	C17—C22—H22	119.6
C10—C9—C8	133.1 (2)	O4—C23—O3	122.6 (2)
C11—C10—C9	118.4 (3)	O4—C23—C24	126.7 (3)
C11—C10—H10	120.8	O3—C23—C24	110.7 (3)
C9—C10—H10	120.8	C23—C24—H24A	109.5
C10—C11—C12	121.0 (3)	C23—C24—H24B	109.5
C10—C11—H11	119.5	H24A—C24—H24B	109.5
C12—C11—H11	119.5	C23—C24—H24C	109.5
C13—C12—C11	121.8 (2)	H24A—C24—H24C	109.5
C13—C12—H12	119.1	H24B—C24—H24C	109.5
C11—C12—H12	119.1	C14—N1—C7	107.05 (16)
C12—C13—C14	117.4 (2)	C14—N1—S1	120.16 (13)
C12—C13—H13	121.3	C7—N1—S1	123.97 (14)
C14—C13—H13	121.3	C23—O3—C16	117.29 (19)
C9—C14—C13	121.9 (2)	O2—S1—O1	119.30 (12)
C9—C14—N1	107.96 (17)	O2—S1—N1	107.07 (10)
C13—C14—N1	130.1 (2)	O1—S1—N1	106.87 (10)
C7—C15—H15A	109.5	O2—S1—C1	109.33 (11)
C7—C15—H15B	109.5	O1—S1—C1	108.81 (11)
H15A—C15—H15B	109.5	N1—S1—C1	104.41 (9)
C7—C15—H15C	109.5

C6—C1—C2—C3	0.7 (4)	C8—C16—C17—C18	53.1 (3)
S1—C1—C2—C3	178.1 (2)	C22—C17—C18—C19	0.6 (4)
C1—C2—C3—C4	0.8 (5)	C16—C17—C18—C19	179.7 (2)
C2—C3—C4—C5	−1.1 (5)	C17—C18—C19—C20	−0.3 (5)
C3—C4—C5—C6	−0.3 (5)	C18—C19—C20—C21	−0.5 (5)
C4—C5—C6—C1	1.9 (4)	C19—C20—C21—C22	1.1 (5)
C2—C1—C6—C5	−2.1 (4)	C20—C21—C22—C17	−0.8 (4)
S1—C1—C6—C5	−179.5 (2)	C18—C17—C22—C21	−0.1 (3)
N1—C7—C8—C9	−0.4 (2)	C16—C17—C22—C21	−179.1 (2)
C15—C7—C8—C9	174.1 (2)	C9—C14—N1—C7	0.9 (2)
N1—C7—C8—C16	178.36 (18)	C13—C14—N1—C7	178.2 (2)
C15—C7—C8—C16	−7.1 (4)	C9—C14—N1—S1	149.55 (15)
C7—C8—C9—C14	0.9 (2)	C13—C14—N1—S1	−33.1 (3)
C16—C8—C9—C14	−177.81 (19)	C8—C7—N1—C14	−0.3 (2)
C7—C8—C9—C10	−177.2 (2)	C15—C7—N1—C14	−175.3 (2)
C16—C8—C9—C10	4.0 (4)	C8—C7—N1—S1	−147.47 (16)
C14—C9—C10—C11	0.1 (4)	C15—C7—N1—S1	37.6 (3)
C8—C9—C10—C11	178.1 (2)	O4—C23—O3—C16	−0.8 (4)
C9—C10—C11—C12	−0.2 (4)	C24—C23—O3—C16	−179.9 (2)
C10—C11—C12—C13	0.4 (5)	C8—C16—O3—C23	−146.89 (19)
C11—C12—C13—C14	−0.5 (4)	C17—C16—O3—C23	90.1 (2)
C10—C9—C14—C13	−0.3 (3)	C14—N1—S1—O2	−179.98 (16)
C8—C9—C14—C13	−178.72 (19)	C7—N1—S1—O2	−36.81 (19)
C10—C9—C14—N1	177.35 (19)	C14—N1—S1—O1	51.11 (18)
C8—C9—C14—N1	−1.1 (2)	C7—N1—S1—O1	−165.73 (17)
C12—C13—C14—C9	0.4 (3)	C14—N1—S1—C1	−64.10 (17)
C12—C13—C14—N1	−176.6 (2)	C7—N1—S1—C1	79.06 (18)
C7—C8—C16—O3	115.6 (2)	C2—C1—S1—O2	−117.5 (2)
C9—C8—C16—O3	−65.9 (2)	C6—C1—S1—O2	59.9 (2)
C7—C8—C16—C17	−122.4 (2)	C2—C1—S1—O1	14.3 (3)
C9—C8—C16—C17	56.2 (3)	C6—C1—S1—O1	−168.25 (19)
O3—C16—C17—C22	−7.9 (3)	C2—C1—S1—N1	128.2 (2)
C8—C16—C17—C22	−127.9 (2)	C6—C1—S1—N1	−54.4 (2)
O3—C16—C17—C18	173.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.39	2.977 (4)	121
C24—H24B···O2ⁱ	0.96	2.58	3.429 (4)	147
C15—H15A···Cg1ⁱⁱ	0.96	2.97	3.590 (3)	124

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₁NO₄S
M_r	419.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	14.3655 (6), 8.3432 (4), 18.6261 (8)
β (°)	108.086 (2)
V (Å³)	2122.12 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.28 × 0.24 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.951, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	23327, 4712, 3030
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.146, 1.01
No. of reflections	4712
No. of parameters	273
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.35

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.39	2.977 (4)	121
C24—H24B···O2ⁱ	0.96	2.58	3.429 (4)	147
C15—H15A···Cg1ⁱⁱ	0.96	2.97	3.590 (3)	124

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x, −y, −z+1.

Acknowledgements

The authors acknowledge SAIF, IIT, Madras, for the data collection.

References

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