Ethyl 2-acetoxy-methyl-1-phenyl-sulfonyl-1H-indole-3-carboxyl-ate.

In the title compound, C(20)H(19)NO(6)S, the phenyl ring of the phenyl-sulfonyl group makes a dihedral angle of 83.35 (5)° with the indole ring system. The mol-ecular structure exhibits a number of short intramolecular C-H⋯O contacts.

Related literature

For the biological activity of indole derivatives, see: Andreani et al. (2001 ▶); Quetin-Leclercq (1994 ▶); Mukhopadhyay et al. (1981 ▶); Singh et al. (2000 ▶). For related structures, see: Chakkaravarthi et al. (2007 ▶, 2008 ▶); Gunasekaran et al. (2009 ▶); For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H19NO6S

M = 401.42

Orthorhombic,

a = 18.9097 (6) Å

b = 7.9737 (2) Å

c = 24.7877 (7) Å

V = 3737.50 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.21 mm−1

T = 295 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.949, T max = 0.959

28247 measured reflections

5788 independent reflections

3533 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.153

S = 1.01

5788 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.28 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/S1600536809029985/gk2226sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809029985/gk2226Isup2.hkl

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

C20H19NO6S	F(000) = 1680
Mr = 401.42	Dx = 1.427 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6552 reflections
a = 18.9097 (6) Å	θ = 2.7–27.1°
b = 7.9737 (2) Å	µ = 0.21 mm−1
c = 24.7877 (7) Å	T = 295 K
V = 3737.50 (18) Å3	Block, colourless
Z = 8	0.25 × 0.20 × 0.20 mm

Bruker APEXII CCD diffractometer	5788 independent reflections
Radiation source: fine-focus sealed tube	3533 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 0 pixels mm-1	θmax = 31.6°, θmin = 2.0°
ω and φ scans	h = −27→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→8
Tmin = 0.949, Tmax = 0.959	l = −36→36
28247 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0697P)2 + 1.0858P] where P = (Fo2 + 2Fc2)/3
5788 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.68111 (9)	0.2922 (2)	0.13401 (7)	0.0409 (4)
C2	0.66359 (10)	0.3751 (3)	0.18121 (7)	0.0483 (4)
H2	0.6165	0.3879	0.1913	0.058*
C3	0.71703 (11)	0.4382 (3)	0.21287 (8)	0.0541 (5)
H3	0.7062	0.4961	0.2444	0.065*
C4	0.78647 (11)	0.4159 (3)	0.19792 (9)	0.0558 (5)
H4	0.8224	0.4567	0.2199	0.067*
C5	0.80341 (11)	0.3345 (3)	0.15112 (9)	0.0552 (5)
H5	0.8506	0.3214	0.1413	0.066*
C6	0.75066 (11)	0.2720 (3)	0.11846 (8)	0.0483 (4)
H6	0.7617	0.2170	0.0865	0.058*
C7	0.60056 (10)	0.4924 (2)	0.03978 (6)	0.0428 (4)
C8	0.66197 (11)	0.4833 (3)	0.00964 (7)	0.0541 (5)
H8	0.6895	0.3868	0.0088	0.065*
C9	0.68026 (13)	0.6250 (3)	−0.01919 (8)	0.0637 (6)
H9	0.7214	0.6239	−0.0397	0.076*
C10	0.63942 (13)	0.7675 (3)	−0.01839 (8)	0.0625 (6)
H10	0.6535	0.8601	−0.0385	0.075*
C11	0.57857 (12)	0.7761 (3)	0.01128 (7)	0.0525 (5)
H11	0.5511	0.8729	0.0114	0.063*
C12	0.55875 (10)	0.6358 (2)	0.04138 (6)	0.0430 (4)
C13	0.49985 (10)	0.6010 (2)	0.07648 (6)	0.0413 (4)
C14	0.50652 (9)	0.4409 (2)	0.09542 (6)	0.0404 (4)
C15	0.44401 (11)	0.7252 (3)	0.08755 (7)	0.0494 (5)
C16	0.33828 (13)	0.7855 (4)	0.13344 (13)	0.0798 (8)
H16A	0.3227	0.8383	0.1002	0.096*
H16B	0.3533	0.8727	0.1582	0.096*
C17	0.28112 (17)	0.6899 (4)	0.15688 (15)	0.1048 (11)
H17A	0.2638	0.6106	0.1309	0.157*
H17B	0.2436	0.7644	0.1671	0.157*
H17C	0.2980	0.6313	0.1882	0.157*
C18	0.45723 (10)	0.3415 (3)	0.12950 (7)	0.0471 (4)
H18A	0.4095	0.3849	0.1262	0.057*
H18B	0.4573	0.2250	0.1182	0.057*
C19	0.45014 (11)	0.2553 (3)	0.22036 (8)	0.0537 (5)
C20	0.48239 (14)	0.2728 (4)	0.27501 (9)	0.0738 (7)
H20A	0.4577	0.2020	0.3001	0.111*
H20B	0.4789	0.3874	0.2866	0.111*
H20C	0.5312	0.2403	0.2735	0.111*
N1	0.56802 (8)	0.37097 (19)	0.07288 (6)	0.0430 (3)
O1	0.56787 (8)	0.10956 (18)	0.12805 (7)	0.0627 (4)
O2	0.64517 (9)	0.13016 (19)	0.04850 (6)	0.0663 (4)
O3	0.44205 (10)	0.8600 (2)	0.06699 (8)	0.0857 (6)
O4	0.39629 (8)	0.6727 (2)	0.12256 (6)	0.0641 (4)
O5	0.48159 (7)	0.35577 (17)	0.18482 (5)	0.0502 (3)
O6	0.40269 (11)	0.1643 (3)	0.20854 (7)	0.0913 (6)
S1	0.61405 (3)	0.20341 (6)	0.09468 (2)	0.04808 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0439 (9)	0.0323 (10)	0.0464 (8)	0.0010 (7)	−0.0041 (7)	0.0052 (7)
C2	0.0451 (10)	0.0481 (12)	0.0516 (9)	0.0023 (9)	0.0002 (8)	0.0016 (8)
C3	0.0603 (12)	0.0513 (13)	0.0508 (10)	−0.0009 (10)	−0.0050 (9)	−0.0036 (9)
C4	0.0541 (12)	0.0504 (13)	0.0631 (11)	−0.0073 (9)	−0.0138 (9)	0.0040 (9)
C5	0.0441 (10)	0.0516 (13)	0.0698 (12)	−0.0025 (9)	0.0003 (9)	0.0104 (10)
C6	0.0504 (10)	0.0405 (12)	0.0541 (9)	0.0027 (8)	0.0030 (8)	0.0026 (8)
C7	0.0524 (10)	0.0400 (11)	0.0359 (7)	−0.0054 (8)	−0.0076 (7)	−0.0011 (7)
C8	0.0604 (12)	0.0565 (13)	0.0454 (9)	−0.0010 (10)	0.0001 (8)	−0.0051 (9)
C9	0.0693 (14)	0.0767 (17)	0.0452 (10)	−0.0160 (12)	0.0061 (9)	−0.0028 (10)
C10	0.0826 (15)	0.0570 (15)	0.0478 (10)	−0.0208 (12)	−0.0024 (10)	0.0080 (9)
C11	0.0728 (13)	0.0397 (12)	0.0450 (9)	−0.0074 (9)	−0.0084 (9)	0.0026 (8)
C12	0.0551 (10)	0.0391 (11)	0.0348 (7)	−0.0054 (8)	−0.0106 (7)	−0.0035 (7)
C13	0.0491 (10)	0.0381 (10)	0.0366 (7)	−0.0010 (8)	−0.0114 (7)	−0.0010 (7)
C14	0.0420 (9)	0.0404 (11)	0.0389 (8)	−0.0030 (7)	−0.0104 (7)	0.0011 (7)
C15	0.0537 (11)	0.0463 (13)	0.0482 (9)	0.0039 (9)	−0.0120 (8)	0.0002 (8)
C16	0.0608 (14)	0.0734 (19)	0.1053 (19)	0.0158 (13)	0.0051 (14)	−0.0091 (15)
C17	0.084 (2)	0.087 (2)	0.144 (3)	0.0024 (17)	0.0415 (19)	−0.005 (2)
C18	0.0438 (9)	0.0490 (12)	0.0485 (9)	−0.0053 (8)	−0.0103 (7)	0.0048 (8)
C19	0.0529 (11)	0.0520 (13)	0.0562 (10)	−0.0001 (10)	0.0086 (9)	0.0086 (9)
C20	0.0858 (17)	0.0825 (18)	0.0532 (11)	−0.0016 (14)	0.0033 (11)	0.0150 (12)
N1	0.0468 (8)	0.0363 (9)	0.0459 (7)	−0.0002 (6)	−0.0071 (6)	0.0036 (6)
O1	0.0561 (8)	0.0387 (9)	0.0933 (11)	−0.0070 (6)	−0.0113 (8)	0.0163 (7)
O2	0.0780 (10)	0.0467 (9)	0.0743 (9)	0.0083 (7)	−0.0106 (8)	−0.0226 (7)
O3	0.0919 (13)	0.0588 (12)	0.1065 (14)	0.0256 (10)	0.0135 (11)	0.0258 (10)
O4	0.0605 (9)	0.0577 (10)	0.0741 (9)	0.0132 (7)	0.0094 (7)	0.0034 (8)
O5	0.0545 (8)	0.0515 (8)	0.0445 (6)	−0.0091 (6)	−0.0059 (6)	0.0084 (6)
O6	0.0865 (12)	0.1080 (15)	0.0792 (11)	−0.0482 (12)	0.0073 (10)	0.0148 (11)
S1	0.0519 (3)	0.0306 (3)	0.0617 (3)	0.0003 (2)	−0.0106 (2)	−0.0024 (2)

C1—C6	1.380 (3)	C13—C15	1.473 (3)
C1—C2	1.384 (3)	C14—N1	1.406 (2)
C1—S1	1.7492 (18)	C14—C18	1.487 (3)
C2—C3	1.375 (3)	C15—O3	1.190 (3)
C2—H2	0.9300	C15—O4	1.320 (2)
C3—C4	1.376 (3)	C16—O4	1.444 (3)
C3—H3	0.9300	C16—C17	1.445 (4)
C4—C5	1.367 (3)	C16—H16A	0.9700
C4—H4	0.9300	C16—H16B	0.9700
C5—C6	1.378 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C7—C8	1.383 (3)	C18—O5	1.451 (2)
C7—C12	1.390 (3)	C18—H18A	0.9700
C7—N1	1.411 (2)	C18—H18B	0.9700
C8—C9	1.380 (3)	C19—O6	1.190 (3)
C8—H8	0.9300	C19—O5	1.331 (2)
C9—C10	1.374 (4)	C19—C20	1.492 (3)
C9—H9	0.9300	C20—H20A	0.9600
C10—C11	1.367 (3)	C20—H20B	0.9600
C10—H10	0.9300	C20—H20C	0.9600
C11—C12	1.396 (3)	N1—S1	1.6838 (16)
C11—H11	0.9300	O1—S1	1.4166 (15)
C12—C13	1.440 (3)	O2—S1	1.4136 (16)
C13—C14	1.366 (3)
C6—C1—C2	121.34 (17)	O3—C15—O4	123.1 (2)
C6—C1—S1	119.21 (14)	O3—C15—C13	123.3 (2)
C2—C1—S1	119.39 (14)	O4—C15—C13	113.56 (17)
C3—C2—C1	118.77 (18)	O4—C16—C17	108.4 (2)
C3—C2—H2	120.6	O4—C16—H16A	110.0
C1—C2—H2	120.6	C17—C16—H16A	110.0
C2—C3—C4	120.01 (19)	O4—C16—H16B	110.0
C2—C3—H3	120.0	C17—C16—H16B	110.0
C4—C3—H3	120.0	H16A—C16—H16B	108.4
C5—C4—C3	120.91 (19)	C16—C17—H17A	109.5
C5—C4—H4	119.5	C16—C17—H17B	109.5
C3—C4—H4	119.5	H17A—C17—H17B	109.5
C4—C5—C6	120.04 (19)	C16—C17—H17C	109.5
C4—C5—H5	120.0	H17A—C17—H17C	109.5
C6—C5—H5	120.0	H17B—C17—H17C	109.5
C5—C6—C1	118.91 (18)	O5—C18—C14	107.23 (14)
C5—C6—H6	120.5	O5—C18—H18A	110.3
C1—C6—H6	120.5	C14—C18—H18A	110.3
C8—C7—C12	122.42 (18)	O5—C18—H18B	110.3
C8—C7—N1	130.14 (18)	C14—C18—H18B	110.3
C12—C7—N1	107.44 (16)	H18A—C18—H18B	108.5
C9—C8—C7	116.6 (2)	O6—C19—O5	122.7 (2)
C9—C8—H8	121.7	O6—C19—C20	126.1 (2)
C7—C8—H8	121.7	O5—C19—C20	111.21 (19)
C10—C9—C8	121.9 (2)	C19—C20—H20A	109.5
C10—C9—H9	119.1	C19—C20—H20B	109.5
C8—C9—H9	119.1	H20A—C20—H20B	109.5
C11—C10—C9	121.5 (2)	C19—C20—H20C	109.5
C11—C10—H10	119.3	H20A—C20—H20C	109.5
C9—C10—H10	119.3	H20B—C20—H20C	109.5
C10—C11—C12	118.2 (2)	C14—N1—C7	108.65 (15)
C10—C11—H11	120.9	C14—N1—S1	127.94 (12)
C12—C11—H11	120.9	C7—N1—S1	120.40 (13)
C7—C12—C11	119.40 (18)	C15—O4—C16	116.42 (19)
C7—C12—C13	107.40 (16)	C19—O5—C18	115.88 (15)
C11—C12—C13	133.20 (19)	O2—S1—O1	120.74 (10)
C14—C13—C12	108.42 (16)	O2—S1—N1	106.44 (9)
C14—C13—C15	129.06 (18)	O1—S1—N1	106.73 (8)
C12—C13—C15	122.52 (17)	O2—S1—C1	108.47 (9)
C13—C14—N1	108.09 (16)	O1—S1—C1	109.60 (9)
C13—C14—C18	129.45 (17)	N1—S1—C1	103.45 (8)
N1—C14—C18	122.22 (16)
C6—C1—C2—C3	0.1 (3)	C12—C13—C15—O4	−177.13 (16)
S1—C1—C2—C3	177.33 (15)	C13—C14—C18—O5	−97.2 (2)
C1—C2—C3—C4	−1.1 (3)	N1—C14—C18—O5	89.02 (19)
C2—C3—C4—C5	1.5 (3)	C13—C14—N1—C7	0.88 (18)
C3—C4—C5—C6	−0.7 (3)	C18—C14—N1—C7	175.80 (14)
C4—C5—C6—C1	−0.4 (3)	C13—C14—N1—S1	160.98 (12)
C2—C1—C6—C5	0.7 (3)	C18—C14—N1—S1	−24.1 (2)
S1—C1—C6—C5	−176.58 (15)	C8—C7—N1—C14	179.48 (17)
C12—C7—C8—C9	0.1 (3)	C12—C7—N1—C14	−0.79 (18)
N1—C7—C8—C9	179.75 (17)	C8—C7—N1—S1	17.6 (2)
C7—C8—C9—C10	−0.5 (3)	C12—C7—N1—S1	−162.66 (12)
C8—C9—C10—C11	0.2 (3)	O3—C15—O4—C16	2.7 (3)
C9—C10—C11—C12	0.4 (3)	C13—C15—O4—C16	−177.34 (18)
C8—C7—C12—C11	0.6 (3)	C17—C16—O4—C15	160.9 (2)
N1—C7—C12—C11	−179.20 (14)	O6—C19—O5—C18	−3.3 (3)
C8—C7—C12—C13	−179.84 (16)	C20—C19—O5—C18	176.40 (18)
N1—C7—C12—C13	0.40 (18)	C14—C18—O5—C19	−170.56 (16)
C10—C11—C12—C7	−0.8 (3)	C14—N1—S1—O2	150.20 (15)
C10—C11—C12—C13	179.76 (18)	C7—N1—S1—O2	−51.75 (15)
C7—C12—C13—C14	0.13 (18)	C14—N1—S1—O1	20.02 (18)
C11—C12—C13—C14	179.66 (18)	C7—N1—S1—O1	178.06 (13)
C7—C12—C13—C15	−179.64 (15)	C14—N1—S1—C1	−95.58 (16)
C11—C12—C13—C15	−0.1 (3)	C7—N1—S1—C1	62.47 (14)
C12—C13—C14—N1	−0.62 (18)	C6—C1—S1—O2	−4.02 (18)
C15—C13—C14—N1	179.14 (16)	C2—C1—S1—O2	178.69 (15)
C12—C13—C14—C18	−175.05 (16)	C6—C1—S1—O1	129.69 (16)
C15—C13—C14—C18	4.7 (3)	C2—C1—S1—O1	−47.59 (17)
C14—C13—C15—O3	−176.9 (2)	C6—C1—S1—N1	−116.77 (15)
C12—C13—C15—O3	2.8 (3)	C2—C1—S1—N1	65.94 (16)
C14—C13—C15—O4	3.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O5	0.93	2.57	3.446 (2)	157
C6—H6···O2	0.93	2.50	2.875 (3)	105
C8—H8···O2	0.93	2.42	2.993 (3)	120
C11—H11···O3	0.93	2.48	3.003 (3)	116
C18—H18A···O4	0.97	2.31	2.886 (3)	117
C18—H18B···O1	0.97	2.30	2.793 (3)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O5	0.93	2.57	3.446 (2)	157
C6—H6⋯O2	0.93	2.50	2.875 (3)	105
C8—H8⋯O2	0.93	2.42	2.993 (3)	120
C11—H11⋯O3	0.93	2.48	3.003 (3)	116
C18—H18A⋯O4	0.97	2.31	2.886 (3)	117
C18—H18B⋯O1	0.97	2.30	2.793 (3)	111