(2-Methyl-1-phenyl-sulfonyl-1H-indol-3-yl)phenyl-methyl acetate.

In the title compound, C(24)H(21)NO(4)S, 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 mol-ecular structure is stabilized by a weak intra-molecular C-H⋯O hydrogen bond. In the crystal, a weak inter-molecular C-H⋯O hydrogen bond and a C-H⋯π inter-action 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 = 419.48

Monoclinic,

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 (; 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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.146

S = 1.01

4712 reflections

273 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.35 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044365/is2478Isup2.hkl

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

C24H21NO4S	F(000) = 880
Mr = 419.48	Dx = 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

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

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(Fo2) + (0.0657P)2 + 0.817P] where P = (Fo2 + 2Fc2)/3
4712 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.35 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) . Cg1 is the centroid of the C17–C22 ring.