Ethyl (2-methyl-1-phenyl­sulfonyl-1H-indole-3-carbon­yl)acetate

In the title compound, C₁₉H₁₇NO₅S, the phenyl ring forms a dihedral angle of 83.67 (4)° with the indole ring system. The mol­ecular structure is stabilized by weak intra­molecular C—H...O inter­actions and the crystal packing is stabilized by weak inter­molecular C—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.050
• wR factor = 0.161
• Data-to-parameter ratio = 25.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.06 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.04 Ratio
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C18    -   C19    ...       1.43 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C16    -   C17    ...       1.53 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Phenylsulfonyl-indole compounds inhibit the HIV-1 RT enzyme in vitro and HTLVIIIb viral spread in MT-4 human T-lymphoid cells (Williams et al., 1993). Indole-3-carboxylate derivatives exhibit significant antihepatitis B virus activities (Chai et al., 2006).

The geometric parameters in the title compound (Fig. 1) agree with the reported values of similar structures (Liu et al., 2007; Senthil Kumar et al., 2006). The phenyl ring forms dihedral angle of 83.67 (4)° with the indole ring system. The five- (N1/C7/C8/C9/C14) and six- (C9–C14) membered rings in the indane group are planar, with a dihedral angle of 1.90 (4)° between these rings.

The sum of the bond angles around N1 (359.95°) indicates that N1 is sp²-hybridized. The torsion angles O2—S1—N1—C14 and O1—S1—N1—C7 [-44.24 (14)° and 9.30 (15)°, respectively] indicate the syn conformation of the sulfonyl moiety.

The details of the hydrogen bonding are given in Table 1. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O interactions and C—H···π interactions involving the C1–C6 (centroid Cg1) and N1/C7–C14 (centroid Cg2) rings.

A similar compound with dibromomethyl group has been reported (Rinderspacher et al., 2007).

Related literature

For releted literature, see: Chai et al. (2006); Liu et al. (2007); Senthil Kumar et al. (2006); Williams et al. (1993). A similar compound with a dibromomethyl group has been reported recently (Rinderspacher et al., 2007).

S2. Experimental

To a solution of ethyl 2-(2-methyl-1H-indole-3-yl)-2-oxoacetate (10 g, 43.2 mmol) in dry dichloromethane (80 ml) under nitrogen, triethylamine (7.8 ml, 56.2 mmol) followed by dimethyl amino pyridine (0.52 g, 4.2 mmol) were added slowly and stirred at 273 K for 30 min. To this benzenesulfonyl chloride (8.3 ml, 64.9 mmol), dry dichloromethane (10 ml) was slowly added at 273 K for 30 min. Then the reaction mixture was stirred at room temperature and poured over crushed ice and extracted with dichloromethane (3 x 20 ml) and dried with sodium sulfate. The solvent was removed under vacuum. Then the crude product was recrystallized from methanol. Single crystals suitable for X-ray analysis were grown by slow evaporation of a methanol solution at room temperature.

S3. Refinement

H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and U_iso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and U_iso(H) = 1.2Ueq(C) for CH₂ and C—H = 0.96 Å and U_iso(H) = 1.5Ueq(C) for CH₃.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Ethyl (2-methyl-1-phenylsulfonyl-1H-indole-3-carbonyl)acetate

Crystal data

C19H17NO5S	F(000) = 776
Mr = 371.40	Dx = 1.410 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 26134 reflections
a = 9.6696 (4) Å	θ = 2.6–29.9°
b = 13.1526 (5) Å	µ = 0.22 mm^−1
c = 13.8048 (5) Å	T = 295 K
β = 94.898 (1)°	Block, colourless
V = 1749.29 (12) Å^3	0.24 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker Kappa APEXII diffractometer	6064 independent reflections
Radiation source: fine-focus sealed tube	4222 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω and φ scans	θmax = 32.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.929, Tmax = 0.958	k = −19→17
25430 measured reflections	l = −20→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0861P)^2 + 0.2836P] where P = (Fo^2 + 2Fc^2)/3
6064 reflections	(Δ/σ)max < 0.001
237 parameters	Δρmax = 0.64 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.22318 (4)	0.34233 (3)	0.23436 (3)	0.04290 (12)
O1	0.31603 (13)	0.42516 (11)	0.22844 (9)	0.0597 (3)
O2	0.26854 (14)	0.24114 (10)	0.21807 (9)	0.0583 (3)
O3	0.05279 (16)	0.40881 (12)	0.65463 (10)	0.0754 (5)
O4	0.37370 (15)	0.46654 (12)	0.63655 (13)	0.0749 (4)
O5	0.21527 (16)	0.58575 (10)	0.66369 (11)	0.0693 (4)
N1	0.17082 (13)	0.34280 (9)	0.34772 (9)	0.0388 (3)
C1	0.07099 (16)	0.36573 (12)	0.15947 (10)	0.0417 (3)
C2	0.0143 (2)	0.28885 (14)	0.10043 (15)	0.0578 (4)
H2	0.0542	0.2245	0.1016	0.069*
C3	−0.1034 (2)	0.31005 (19)	0.03940 (17)	0.0715 (6)
H3	−0.1422	0.2597	−0.0018	0.086*
C4	−0.1632 (2)	0.40435 (17)	0.03917 (16)	0.0676 (5)
H4	−0.2431	0.4172	−0.0014	0.081*
C5	−0.1066 (2)	0.47999 (17)	0.09798 (16)	0.0680 (5)
H5	−0.1480	0.5438	0.0972	0.082*
C6	0.0123 (2)	0.46155 (14)	0.15871 (13)	0.0546 (4)
H6	0.0520	0.5128	0.1983	0.066*
C7	0.19316 (14)	0.41714 (11)	0.42039 (10)	0.0371 (3)
C8	0.12836 (14)	0.38506 (11)	0.49973 (10)	0.0364 (3)
C9	0.05878 (14)	0.29003 (10)	0.47616 (10)	0.0357 (3)
C10	−0.01968 (16)	0.22449 (12)	0.52925 (11)	0.0446 (3)
H10	−0.0400	0.2408	0.5920	0.054*
C11	−0.06630 (19)	0.13474 (13)	0.48590 (14)	0.0539 (4)
H11	−0.1192	0.0903	0.5199	0.065*
C12	−0.0356 (2)	0.10986 (14)	0.39263 (14)	0.0564 (4)
H12	−0.0681	0.0487	0.3655	0.068*
C13	0.04189 (19)	0.17325 (13)	0.33887 (12)	0.0500 (4)
H13	0.0624	0.1560	0.2764	0.060*
C14	0.08790 (15)	0.26386 (11)	0.38203 (10)	0.0370 (3)
C15	0.2699 (2)	0.51382 (13)	0.40713 (13)	0.0523 (4)
H15A	0.2545	0.5597	0.4592	0.078*
H15B	0.2373	0.5443	0.3462	0.078*
H15C	0.3674	0.4997	0.4075	0.078*
C16	0.13428 (16)	0.43055 (12)	0.59581 (11)	0.0440 (3)
C17	0.25701 (18)	0.49730 (13)	0.63227 (12)	0.0484 (4)
C18	0.3215 (3)	0.6517 (2)	0.7133 (2)	0.0904 (8)
H18A	0.2796	0.6933	0.7609	0.109*
H18B	0.3928	0.6101	0.7474	0.109*
C19	0.3829 (4)	0.7157 (2)	0.6453 (3)	0.1093 (11)
H19A	0.4346	0.6749	0.6034	0.164*
H19B	0.4440	0.7634	0.6797	0.164*
H19C	0.3113	0.7519	0.6070	0.164*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.03753 (19)	0.0552 (2)	0.03706 (19)	0.00035 (15)	0.00942 (14)	−0.00083 (15)
O1	0.0494 (6)	0.0800 (9)	0.0516 (7)	−0.0196 (6)	0.0145 (5)	0.0025 (6)
O2	0.0546 (7)	0.0659 (8)	0.0556 (7)	0.0185 (6)	0.0124 (6)	−0.0068 (6)
O3	0.0830 (10)	0.0882 (11)	0.0598 (8)	−0.0327 (8)	0.0346 (7)	−0.0305 (7)
O4	0.0513 (8)	0.0735 (10)	0.0966 (12)	0.0002 (7)	−0.0132 (7)	−0.0058 (8)
O5	0.0733 (9)	0.0544 (8)	0.0792 (10)	−0.0107 (6)	0.0011 (7)	−0.0210 (7)
N1	0.0429 (6)	0.0405 (6)	0.0335 (5)	−0.0052 (5)	0.0057 (5)	−0.0013 (5)
C1	0.0420 (7)	0.0498 (8)	0.0342 (6)	0.0002 (6)	0.0075 (5)	−0.0003 (6)
C2	0.0576 (10)	0.0490 (9)	0.0651 (11)	−0.0013 (8)	−0.0049 (8)	−0.0049 (8)
C3	0.0626 (12)	0.0702 (13)	0.0780 (14)	−0.0122 (10)	−0.0152 (10)	−0.0110 (11)
C4	0.0507 (10)	0.0789 (14)	0.0708 (13)	0.0028 (10)	−0.0082 (9)	0.0054 (11)
C5	0.0670 (12)	0.0669 (12)	0.0688 (12)	0.0197 (10)	−0.0020 (10)	0.0006 (10)
C6	0.0629 (11)	0.0533 (10)	0.0470 (9)	0.0080 (8)	0.0011 (8)	−0.0075 (7)
C7	0.0357 (6)	0.0361 (7)	0.0392 (7)	−0.0022 (5)	0.0022 (5)	−0.0003 (5)
C8	0.0362 (6)	0.0362 (6)	0.0368 (6)	−0.0011 (5)	0.0032 (5)	−0.0026 (5)
C9	0.0332 (6)	0.0374 (7)	0.0363 (6)	−0.0025 (5)	0.0018 (5)	−0.0004 (5)
C10	0.0435 (8)	0.0490 (8)	0.0419 (7)	−0.0093 (6)	0.0072 (6)	0.0007 (6)
C11	0.0547 (9)	0.0502 (9)	0.0570 (10)	−0.0180 (7)	0.0062 (8)	0.0049 (7)
C12	0.0657 (11)	0.0451 (9)	0.0575 (10)	−0.0182 (8)	0.0005 (8)	−0.0070 (7)
C13	0.0599 (10)	0.0465 (8)	0.0436 (8)	−0.0096 (7)	0.0049 (7)	−0.0082 (6)
C14	0.0370 (6)	0.0371 (7)	0.0366 (6)	−0.0032 (5)	0.0020 (5)	0.0000 (5)
C15	0.0599 (10)	0.0434 (8)	0.0541 (9)	−0.0150 (7)	0.0090 (8)	0.0007 (7)
C16	0.0465 (8)	0.0431 (8)	0.0429 (7)	−0.0048 (6)	0.0066 (6)	−0.0088 (6)
C17	0.0514 (9)	0.0490 (8)	0.0435 (8)	−0.0063 (7)	−0.0031 (7)	−0.0027 (7)
C18	0.114 (2)	0.0722 (16)	0.0828 (17)	−0.0360 (14)	−0.0062 (15)	−0.0201 (12)
C19	0.109 (2)	0.0856 (19)	0.127 (3)	−0.0298 (17)	−0.028 (2)	0.0274 (17)

Geometric parameters (Å, º)

S1—O1	1.4185 (13)	C8—C9	1.4433 (19)
S1—O2	1.4251 (13)	C8—C16	1.452 (2)
S1—N1	1.6854 (12)	C9—C14	1.3960 (19)
S1—C1	1.7520 (16)	C9—C10	1.3967 (19)
O3—C16	1.2130 (19)	C10—C11	1.382 (2)
O4—C17	1.195 (2)	C10—H10	0.9300
O5—C17	1.317 (2)	C11—C12	1.385 (3)
O5—C18	1.468 (3)	C11—H11	0.9300
N1—C7	1.4042 (18)	C12—C13	1.379 (2)
N1—C14	1.4178 (18)	C12—H12	0.9300
C1—C6	1.382 (2)	C13—C14	1.389 (2)
C1—C2	1.382 (2)	C13—H13	0.9300
C2—C3	1.385 (3)	C15—H15A	0.9600
C2—H2	0.9300	C15—H15B	0.9600
C3—C4	1.368 (3)	C15—H15C	0.9600
C3—H3	0.9300	C16—C17	1.527 (2)
C4—C5	1.368 (3)	C18—C19	1.427 (4)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.385 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.3738 (19)	C19—H19C	0.9600
C7—C15	1.492 (2)
O1—S1—O2	120.22 (8)	C11—C10—H10	120.9
O1—S1—N1	107.01 (7)	C9—C10—H10	120.9
O2—S1—N1	105.72 (7)	C10—C11—C12	121.10 (15)
O1—S1—C1	109.57 (8)	C10—C11—H11	119.4
O2—S1—C1	108.98 (8)	C12—C11—H11	119.4
N1—S1—C1	104.09 (6)	C13—C12—C11	121.79 (16)
C17—O5—C18	116.98 (19)	C13—C12—H12	119.1
C7—N1—C14	109.15 (11)	C11—C12—H12	119.1
C7—N1—S1	128.74 (10)	C12—C13—C14	117.18 (15)
C14—N1—S1	122.06 (10)	C12—C13—H13	121.4
C6—C1—C2	121.39 (16)	C14—C13—H13	121.4
C6—C1—S1	119.23 (13)	C13—C14—C9	121.89 (13)
C2—C1—S1	119.36 (13)	C13—C14—N1	130.91 (13)
C1—C2—C3	118.37 (18)	C9—C14—N1	107.17 (12)
C1—C2—H2	120.8	C7—C15—H15A	109.5
C3—C2—H2	120.8	C7—C15—H15B	109.5
C4—C3—C2	120.57 (19)	H15A—C15—H15B	109.5
C4—C3—H3	119.7	C7—C15—H15C	109.5
C2—C3—H3	119.7	H15A—C15—H15C	109.5
C3—C4—C5	120.70 (19)	H15B—C15—H15C	109.5
C3—C4—H4	119.7	O3—C16—C8	122.50 (15)
C5—C4—H4	119.7	O3—C16—C17	116.49 (14)
C4—C5—C6	120.06 (19)	C8—C16—C17	120.47 (13)
C4—C5—H5	120.0	O4—C17—O5	126.67 (17)
C6—C5—H5	120.0	O4—C17—C16	121.70 (16)
C1—C6—C5	118.90 (17)	O5—C17—C16	111.42 (15)
C1—C6—H6	120.6	C19—C18—O5	110.8 (2)
C5—C6—H6	120.6	C19—C18—H18A	109.5
C8—C7—N1	107.63 (12)	O5—C18—H18A	109.5
C8—C7—C15	128.71 (14)	C19—C18—H18B	109.5
N1—C7—C15	123.62 (13)	O5—C18—H18B	109.5
C7—C8—C9	108.77 (12)	H18A—C18—H18B	108.1
C7—C8—C16	128.08 (13)	C18—C19—H19A	109.5
C9—C8—C16	122.96 (13)	C18—C19—H19B	109.5
C14—C9—C10	119.87 (13)	H19A—C19—H19B	109.5
C14—C9—C8	107.22 (12)	C18—C19—H19C	109.5
C10—C9—C8	132.83 (13)	H19A—C19—H19C	109.5
C11—C10—C9	118.15 (15)	H19B—C19—H19C	109.5
O1—S1—N1—C7	9.30 (15)	C16—C8—C9—C14	−173.10 (14)
O2—S1—N1—C7	138.55 (13)	C7—C8—C9—C10	178.99 (16)
C1—S1—N1—C7	−106.67 (14)	C16—C8—C9—C10	3.6 (3)
O1—S1—N1—C14	−173.50 (12)	C14—C9—C10—C11	0.0 (2)
O2—S1—N1—C14	−44.24 (14)	C8—C9—C10—C11	−176.40 (16)
C1—S1—N1—C14	70.53 (13)	C9—C10—C11—C12	0.4 (3)
O1—S1—C1—C6	−42.83 (15)	C10—C11—C12—C13	−0.3 (3)
O2—S1—C1—C6	−176.23 (13)	C11—C12—C13—C14	−0.2 (3)
N1—S1—C1—C6	71.33 (14)	C12—C13—C14—C9	0.6 (3)
O1—S1—C1—C2	135.39 (14)	C12—C13—C14—N1	178.30 (16)
O2—S1—C1—C2	1.99 (16)	C10—C9—C14—C13	−0.5 (2)
N1—S1—C1—C2	−110.45 (14)	C8—C9—C14—C13	176.71 (15)
C6—C1—C2—C3	0.3 (3)	C10—C9—C14—N1	−178.69 (13)
S1—C1—C2—C3	−177.86 (16)	C8—C9—C14—N1	−1.45 (16)
C1—C2—C3—C4	−1.2 (3)	C7—N1—C14—C13	−177.75 (16)
C2—C3—C4—C5	1.1 (4)	S1—N1—C14—C13	4.6 (2)
C3—C4—C5—C6	−0.1 (4)	C7—N1—C14—C9	0.18 (16)
C2—C1—C6—C5	0.7 (3)	S1—N1—C14—C9	−177.51 (10)
S1—C1—C6—C5	178.83 (15)	C7—C8—C16—O3	165.01 (17)
C4—C5—C6—C1	−0.8 (3)	C9—C8—C16—O3	−20.6 (3)
C14—N1—C7—C8	1.23 (16)	C7—C8—C16—C17	−23.7 (2)
S1—N1—C7—C8	178.72 (11)	C9—C8—C16—C17	150.71 (15)
C14—N1—C7—C15	−176.61 (14)	C18—O5—C17—O4	−3.1 (3)
S1—N1—C7—C15	0.9 (2)	C18—O5—C17—C16	171.70 (18)
N1—C7—C8—C9	−2.13 (16)	O3—C16—C17—O4	114.6 (2)
C15—C7—C8—C9	175.57 (15)	C8—C16—C17—O4	−57.2 (2)
N1—C7—C8—C16	172.93 (14)	O3—C16—C17—O5	−60.5 (2)
C15—C7—C8—C16	−9.4 (3)	C8—C16—C17—O5	127.69 (16)
C7—C8—C9—C14	2.26 (16)	C17—O5—C18—C19	89.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3^i	0.93	2.56	3.197 (2)	126
C2—H2···O2	0.93	2.52	2.897 (2)	104
C10—H10···O3	0.93	2.51	3.026 (2)	115
C13—H13···O2	0.93	2.48	3.001 (2)	116
C15—H15B···O1	0.96	2.43	2.798 (2)	103
C3—H3···Cg1^ii	0.93	2.70	3.524	148
C4—H4···Cg2^ii	0.93	2.90	3.619	135

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