Ethyl 1-phenyl-sulfonyl-1H-indole-2-carboxyl-ate.

In the title compound, C(17)H(15)NO(4)S, the six-membered ring of the indole unit makes a dihedral angle of 72.40 (5)° with the phenyl ring. The mol-ecular structure features a short C-H⋯O contact.

Related literature

For the biological activity of Indole derivatives, see: Joshi & Chand (1982 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶); For a related structure, see: Chakkaravarthi et al. (2010 ▶).

Experimental

Crystal data

C17H15NO4S

M = 329.36

Monoclinic,

a = 10.6936 (6) Å

b = 7.5331 (4) Å

c = 19.5654 (12) Å

β = 96.647 (2)°

V = 1565.52 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.960

35524 measured reflections

4353 independent reflections

3245 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.129

S = 1.02

4353 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.23 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 datablock(s) global, I. DOI: 10.1107/S1600536811035392/bt5624sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035392/bt5624Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035392/bt5624Isup3.cml

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

C17H15NO4S	F(000) = 688
Mr = 329.36	Dx = 1.397 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2Yn	Cell parameters from 4353 reflections
a = 10.6936 (6) Å	θ = 2.1–29.5°
b = 7.5331 (4) Å	µ = 0.23 mm−1
c = 19.5654 (12) Å	T = 295 K
β = 96.647 (2)°	Block, colourless
V = 1565.52 (15) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	4353 independent reflections
Radiation source: fine-focus sealed tube	3245 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 0 pixels mm-1	θmax = 29.5°, θmin = 2.1°
ω and φ scans	h = −14→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.952, Tmax = 0.960	l = −26→27
35524 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0661P)2 + 0.3737P] where P = (Fo2 + 2Fc2)/3
4353 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.75477 (14)	0.1614 (2)	0.14296 (8)	0.0459 (3)
C2	0.76555 (18)	0.1553 (3)	0.07299 (10)	0.0595 (4)
H2	0.6951	0.1613	0.0404	0.071*
C3	0.8851 (2)	0.1399 (3)	0.05402 (12)	0.0707 (5)
H3	0.8950	0.1358	0.0075	0.085*
C4	0.99095 (19)	0.1305 (3)	0.10177 (13)	0.0746 (6)
H4	1.0700	0.1195	0.0868	0.090*
C5	0.98078 (17)	0.1371 (3)	0.16998 (12)	0.0667 (5)
H5	1.0523	0.1320	0.2019	0.080*
C6	0.86132 (15)	0.1518 (2)	0.19186 (9)	0.0500 (4)
C7	0.82011 (15)	0.1562 (2)	0.25786 (9)	0.0517 (4)
H7	0.8717	0.1525	0.2995	0.062*
C8	0.69340 (14)	0.1666 (2)	0.25026 (8)	0.0444 (3)
C9	0.61219 (15)	0.1458 (2)	0.30554 (9)	0.0479 (4)
C10	0.6183 (2)	0.1412 (3)	0.42624 (10)	0.0699 (5)
H10A	0.5795	0.0247	0.4225	0.084*
H10B	0.5535	0.2287	0.4314	0.084*
C11	0.7173 (3)	0.1476 (4)	0.48626 (12)	0.0924 (8)
H11A	0.7850	0.0694	0.4783	0.139*
H11B	0.6821	0.1109	0.5269	0.139*
H11C	0.7487	0.2667	0.4922	0.139*
C12	0.42232 (13)	0.0165 (2)	0.14176 (8)	0.0443 (3)
C13	0.31930 (15)	−0.0030 (3)	0.17714 (10)	0.0562 (4)
H13	0.2935	0.0894	0.2038	0.067*
C14	0.25463 (18)	−0.1627 (3)	0.17237 (11)	0.0653 (5)
H14	0.1838	−0.1774	0.1952	0.078*
C15	0.2945 (2)	−0.2984 (3)	0.13425 (11)	0.0682 (5)
H15	0.2515	−0.4060	0.1320	0.082*
C16	0.3978 (2)	−0.2779 (3)	0.09909 (11)	0.0661 (5)
H16	0.4242	−0.3715	0.0733	0.079*
C17	0.46224 (17)	−0.1190 (2)	0.10196 (9)	0.0558 (4)
H17	0.5311	−0.1034	0.0776	0.067*
N1	0.64889 (11)	0.17160 (18)	0.17945 (7)	0.0445 (3)
O1	0.51424 (12)	0.27385 (18)	0.07617 (7)	0.0626 (3)
O2	0.44931 (11)	0.33875 (16)	0.18971 (7)	0.0589 (3)
O3	0.50501 (12)	0.09756 (19)	0.29867 (7)	0.0646 (3)
O4	0.67930 (12)	0.17905 (19)	0.36602 (6)	0.0611 (3)
S1	0.50234 (3)	0.22047 (5)	0.14475 (2)	0.04621 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0410 (8)	0.0423 (7)	0.0540 (9)	0.0003 (6)	0.0037 (6)	0.0018 (6)
C2	0.0572 (10)	0.0664 (11)	0.0551 (10)	−0.0002 (8)	0.0071 (8)	0.0046 (8)
C3	0.0731 (13)	0.0750 (13)	0.0678 (12)	0.0045 (10)	0.0247 (10)	0.0025 (10)
C4	0.0519 (11)	0.0801 (14)	0.0961 (17)	0.0050 (10)	0.0263 (11)	0.0025 (12)
C5	0.0409 (9)	0.0747 (13)	0.0846 (14)	0.0047 (8)	0.0071 (9)	−0.0044 (10)
C6	0.0391 (7)	0.0463 (8)	0.0633 (10)	0.0011 (6)	0.0004 (7)	−0.0017 (7)
C7	0.0412 (8)	0.0554 (9)	0.0554 (9)	0.0053 (7)	−0.0068 (7)	−0.0053 (7)
C8	0.0407 (7)	0.0433 (7)	0.0472 (8)	0.0035 (6)	−0.0035 (6)	−0.0010 (6)
C9	0.0459 (8)	0.0452 (8)	0.0510 (9)	0.0076 (6)	−0.0011 (7)	0.0006 (6)
C10	0.0802 (14)	0.0781 (13)	0.0521 (11)	0.0125 (11)	0.0106 (9)	0.0039 (9)
C11	0.116 (2)	0.1060 (19)	0.0524 (12)	0.0233 (16)	−0.0021 (12)	0.0063 (12)
C12	0.0362 (7)	0.0461 (7)	0.0474 (8)	0.0036 (6)	−0.0083 (6)	0.0005 (6)
C13	0.0407 (8)	0.0596 (10)	0.0672 (11)	0.0006 (7)	0.0012 (7)	−0.0057 (8)
C14	0.0487 (10)	0.0690 (11)	0.0761 (13)	−0.0103 (8)	−0.0017 (9)	0.0078 (10)
C15	0.0701 (12)	0.0534 (10)	0.0747 (13)	−0.0123 (9)	−0.0188 (10)	0.0068 (9)
C16	0.0773 (13)	0.0498 (9)	0.0666 (12)	0.0052 (9)	−0.0111 (10)	−0.0081 (8)
C17	0.0544 (9)	0.0557 (9)	0.0551 (10)	0.0061 (7)	−0.0027 (7)	−0.0051 (7)
N1	0.0352 (6)	0.0516 (7)	0.0452 (7)	0.0011 (5)	−0.0015 (5)	0.0022 (5)
O1	0.0546 (7)	0.0708 (8)	0.0595 (8)	0.0042 (6)	−0.0051 (6)	0.0204 (6)
O2	0.0503 (7)	0.0461 (6)	0.0784 (9)	0.0119 (5)	−0.0001 (6)	−0.0040 (6)
O3	0.0481 (7)	0.0822 (9)	0.0629 (8)	−0.0033 (6)	0.0042 (6)	0.0031 (7)
O4	0.0590 (7)	0.0773 (8)	0.0458 (7)	0.0003 (6)	0.0003 (5)	−0.0031 (6)
S1	0.0382 (2)	0.0439 (2)	0.0542 (2)	0.00539 (14)	−0.00468 (15)	0.00506 (16)

C1—C2	1.388 (2)	C10—H10A	0.9700
C1—C6	1.402 (2)	C10—H10B	0.9700
C1—N1	1.409 (2)	C11—H11A	0.9600
C2—C3	1.376 (3)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.384 (3)	C12—C13	1.375 (2)
C3—H3	0.9300	C12—C17	1.381 (2)
C4—C5	1.352 (3)	C12—S1	1.7567 (16)
C4—H4	0.9300	C13—C14	1.386 (3)
C5—C6	1.398 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.363 (3)
C6—C7	1.412 (3)	C14—H14	0.9300
C7—C8	1.348 (2)	C15—C16	1.376 (3)
C7—H7	0.9300	C15—H15	0.9300
C8—N1	1.412 (2)	C16—C17	1.379 (3)
C8—C9	1.472 (2)	C16—H16	0.9300
C9—O3	1.195 (2)	C17—H17	0.9300
C9—O4	1.335 (2)	N1—S1	1.6752 (13)
C10—O4	1.440 (2)	O1—S1	1.4204 (13)
C10—C11	1.488 (3)	O2—S1	1.4159 (13)
C2—C1—C6	121.18 (16)	C10—C11—H11B	109.5
C2—C1—N1	131.69 (15)	H11A—C11—H11B	109.5
C6—C1—N1	107.11 (14)	C10—C11—H11C	109.5
C3—C2—C1	117.02 (18)	H11A—C11—H11C	109.5
C3—C2—H2	121.5	H11B—C11—H11C	109.5
C1—C2—H2	121.5	C13—C12—C17	121.55 (16)
C2—C3—C4	122.4 (2)	C13—C12—S1	119.47 (13)
C2—C3—H3	118.8	C17—C12—S1	118.95 (13)
C4—C3—H3	118.8	C12—C13—C14	118.77 (18)
C5—C4—C3	120.76 (18)	C12—C13—H13	120.6
C5—C4—H4	119.6	C14—C13—H13	120.6
C3—C4—H4	119.6	C15—C14—C13	120.20 (19)
C4—C5—C6	119.07 (19)	C15—C14—H14	119.9
C4—C5—H5	120.5	C13—C14—H14	119.9
C6—C5—H5	120.5	C14—C15—C16	120.64 (18)
C5—C6—C1	119.62 (18)	C14—C15—H15	119.7
C5—C6—C7	132.45 (17)	C16—C15—H15	119.7
C1—C6—C7	107.92 (14)	C15—C16—C17	120.23 (18)
C8—C7—C6	108.45 (15)	C15—C16—H16	119.9
C8—C7—H7	125.8	C17—C16—H16	119.9
C6—C7—H7	125.8	C16—C17—C12	118.60 (18)
C7—C8—N1	109.27 (14)	C16—C17—H17	120.7
C7—C8—C9	125.71 (15)	C12—C17—H17	120.7
N1—C8—C9	124.28 (13)	C1—N1—C8	107.24 (12)
O3—C9—O4	124.55 (16)	C1—N1—S1	125.14 (11)
O3—C9—C8	126.12 (16)	C8—N1—S1	126.64 (11)
O4—C9—C8	109.22 (14)	C9—O4—C10	116.12 (15)
O4—C10—C11	106.90 (19)	O2—S1—O1	119.66 (8)
O4—C10—H10A	110.3	O2—S1—N1	108.04 (7)
C11—C10—H10A	110.3	O1—S1—N1	105.26 (7)
O4—C10—H10B	110.3	O2—S1—C12	110.04 (8)
C11—C10—H10B	110.3	O1—S1—C12	108.23 (8)
H10A—C10—H10B	108.6	N1—S1—C12	104.50 (7)
C10—C11—H11A	109.5
C6—C1—C2—C3	−0.2 (3)	C13—C12—C17—C16	−1.2 (2)
N1—C1—C2—C3	−178.06 (18)	S1—C12—C17—C16	−179.06 (14)
C1—C2—C3—C4	0.1 (3)	C2—C1—N1—C8	177.65 (17)
C2—C3—C4—C5	−0.4 (3)	C6—C1—N1—C8	−0.45 (17)
C3—C4—C5—C6	0.7 (3)	C2—C1—N1—S1	−13.1 (3)
C4—C5—C6—C1	−0.7 (3)	C6—C1—N1—S1	168.80 (11)
C4—C5—C6—C7	177.8 (2)	C7—C8—N1—C1	0.77 (18)
C2—C1—C6—C5	0.5 (3)	C9—C8—N1—C1	−169.90 (14)
N1—C1—C6—C5	178.83 (16)	C7—C8—N1—S1	−168.27 (12)
C2—C1—C6—C7	−178.36 (16)	C9—C8—N1—S1	21.1 (2)
N1—C1—C6—C7	−0.01 (18)	O3—C9—O4—C10	4.4 (2)
C5—C6—C7—C8	−178.14 (19)	C8—C9—O4—C10	−171.90 (15)
C1—C6—C7—C8	0.49 (19)	C11—C10—O4—C9	167.30 (18)
C6—C7—C8—N1	−0.78 (19)	C1—N1—S1—O2	−137.60 (13)
C6—C7—C8—C9	169.72 (15)	C8—N1—S1—O2	29.58 (15)
C7—C8—C9—O3	−153.97 (18)	C1—N1—S1—O1	−8.67 (15)
N1—C8—C9—O3	15.2 (3)	C8—N1—S1—O1	158.50 (13)
C7—C8—C9—O4	22.3 (2)	C1—N1—S1—C12	105.25 (14)
N1—C8—C9—O4	−168.58 (14)	C8—N1—S1—C12	−87.58 (14)
C17—C12—C13—C14	0.0 (2)	C13—C12—S1—O2	3.79 (15)
S1—C12—C13—C14	177.82 (13)	C17—C12—S1—O2	−178.30 (12)
C12—C13—C14—C15	1.2 (3)	C13—C12—S1—O1	−128.64 (13)
C13—C14—C15—C16	−1.2 (3)	C17—C12—S1—O1	49.27 (14)
C14—C15—C16—C17	−0.1 (3)	C13—C12—S1—N1	119.56 (13)
C15—C16—C17—C12	1.3 (3)	C17—C12—S1—N1	−62.53 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.29	2.839 (2)	117.
C13—H13···O2	0.93	2.55	2.923 (2)	105.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1	0.93	2.29	2.839 (2)	117