Ethyl 2-[(N-meth­oxy-N-methyl­carbamo­yl)meth­yl]-1-(phenyl­sulfon­yl)-1H-indole-3-carboxyl­ate

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

doi:10.1107/S1600536808014979

organic compounds

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Volume 64| Part 6| June 2008| Page o1139

doi:10.1107/S1600536808014979

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Ethyl 2-[(N-methoxy-N-methylcarbamoyl)methyl]-1-(phenylsulfonyl)-1H-indole-3-carboxylate

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

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 14 May 2008; accepted 17 May 2008; online 21 May 2008)

In the title compound, C₂₁H₂₂N₂O₆S, the phenyl ring forms a dihedral angle of 83.17 (7)° with the indole ring system. The methyl group of the ester unit is disordered over two positions with site occupancies of 0.635 (6) and 0.365 (6). In the crystal structure, weak intramolecular C—H⋯O interactions and intermolecular C—H⋯O, C—H⋯N and C—H⋯π interactions are observed.

Related literature

For biological activity, see: Merck (1973 , 1974 ); Hendi & Basangoudar (1981 ); Kolocouris et al. (1994 ); Uchida et al. (1989 ); Shaaban et al. (1977 ). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 , 2008 ).

Experimental

Crystal data

C₂₁H₂₂N₂O₆S
M_r = 430.47
Monoclinic, P 2₁ /c
a = 8.5827 (3) Å
b = 11.0783 (5) Å
c = 21.7433 (8) Å
β = 97.091 (2)°
V = 2051.58 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 295 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.914, T_max = 0.961
29808 measured reflections
7666 independent reflections
3947 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.238
S = 1.04
7666 reflections
285 parameters
20 restraints
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.62 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2	0.93	2.54	2.896 (3)	103
C6—H6⋯O3	0.93	2.37	3.218 (3)	152
C10—H10⋯O6	0.93	2.46	2.969 (4)	114
C13—H13⋯O2	0.93	2.51	3.039 (4)	117
C15—H15A⋯O5	0.97	2.39	2.844 (3)	108
C15—H15B⋯O1	0.97	2.17	2.847 (3)	126
C17—H17B⋯O5ⁱ	0.96	2.47	3.420 (3)	173
C20—H20C⋯N1ⁱⁱ	0.97	2.45	3.351 (4)	155
C20—H20C⋯O2ⁱⁱ	0.97	2.53	3.343 (4)	142
C21A—H21F⋯Cgⁱⁱⁱ	0.96	2.80	3.196 (13)	105
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+2; (iii) -x, -y+2, -z. Cg is the centroid of the C1–C6 phenyl ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014979/is2294sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014979/is2294Isup2.hkl

checkCIF report

Comment top

In continuation of our studies of indole derivatives, which are found to possess antihypertensive (Merck, 1973), muscle-relaxant (Hendi & Basangoudar, 1981), antiviral (Kolocouris et al., 1994) antiulcer (Uchida et al., 1989) and analgesic (Shaaban et al., 1977) activities, we determined the crystal structure of the title compound, (I). The geometric parameters of the molecule of (I) (Fig. 1) agree well with those reported for similar structures (Chakkaravarthi et al., 2007, 2008).

The plane of phenyl ring forms 83.17 (7)° with the indole ring system. The plane of N1—S1—C1 forms the dihedral angles of 39.36 (9)° and 69.28 (9)°, respectively, with the phenyl ring and the indole ring. The carboxylate group and N-methoxy-N-methylcarbamide group are approximately orthogonal to each other [dihedral angle 88.45 (1)°] and makes the dihedral angles of 18.61 (14)° and 84.81 (7)°, respectively, with the indole ring. The sum of bond angles around N1 (359.69°) indicates that N1 is sp²-hybridized. The torsion angles O1—S1—N1—C7 and O2—S1—N1—C14 [-9.9 (2)° and 48.3 (2)°, respectively] indicate the syn conformation of the sulfonyl moiety.

The methyl C atom of the ester group is disordered over two positions with occupancies of 0.635 (6) and 0.365 (6). The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing (Fig. 2) exhibits weak intermolecular C—H···O, C—H···N interactions and a C—H···π interaction involving the ring C1—C6 (centroid Cg) (Table 1).

Related literature top

For biological activity, see: Merck (1973, 1974); Hendi & Basangoudar (1981); Kolocouris et al. (1994); Uchida et al. (1989); Shaaban et al. (1977). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008). Cg is the centroid of the C1–C6 phenyl ring.

Experimental top

CO gas was passed through the stirred solution of Ethyl-1-phenylsulfonyl-2-bromomethylindole-3-carboxylate (5.0 g, 11.84 mmol) in CH₃CN (60 ml). To this, PdCl₂ (200 mg, 1.12 mmol) and an in situ prepared HN(OMe)Me solution [HCl.HN(OMe)Me (230 mg, 23.71 mmol) in CH₃CN (30 ml)], K₂CO₃ (3.27 g, 23.69 mmol) and H₂O (0.5 ml) were added, stirred for 1 h and filtered] were added. Usual work up followed by evaporation of solvent to give sticky product and the crude product was purified by column chromatography (silica gel) using hexane and ethyl acetate mixture (7:3). Crystals suitable for X-ray analysis were grown by slow evaporation of ethyl acetate solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	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 c axis. Intermolecular Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

Ethyl 2-[(N-methoxy-N-methylcarbamoyl)methyl]-1-(phenylsulfonyl)- 1H-indole-3-carboxylate top

Crystal data top

C₂₁H₂₂N₂O₆S	F(000) = 904
M_r = 430.47	D_x = 1.394 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8381 reflections
a = 8.5827 (3) Å	θ = 2.4–29.8°
b = 11.0783 (5) Å	µ = 0.20 mm⁻¹
c = 21.7433 (8) Å	T = 295 K
β = 97.091 (2)°	Block, colourless
V = 2051.58 (14) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker KappaAPEX2 diffractometer	7666 independent reflections
Radiation source: fine-focus sealed tube	3947 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scans	θ_max = 32.9°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
T_min = 0.914, T_max = 0.961	k = −16→16
29808 measured reflections	l = −33→32

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.238	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1138P)² + 0.5762P] where P = (F_o² + 2F_c²)/3
7666 reflections	(Δ/σ)_max < 0.001
285 parameters	Δρ_max = 0.82 e Å⁻³
20 restraints	Δρ_min = −0.62 e Å⁻³

Crystal data top

C₂₁H₂₂N₂O₆S	V = 2051.58 (14) Å³
M_r = 430.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5827 (3) Å	µ = 0.20 mm⁻¹
b = 11.0783 (5) Å	T = 295 K
c = 21.7433 (8) Å	0.30 × 0.20 × 0.20 mm
β = 97.091 (2)°

Data collection top

Bruker KappaAPEX2 diffractometer	7666 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3947 reflections with I > 2σ(I)
T_min = 0.914, T_max = 0.961	R_int = 0.029
29808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	20 restraints
wR(F²) = 0.238	H-atom parameters constrained
S = 1.04	Δρ_max = 0.82 e Å⁻³
7666 reflections	Δρ_min = −0.62 e Å⁻³
285 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.67495 (6)	0.03757 (6)	0.79732 (2)	0.05333 (19)
O1	0.5718 (2)	0.1330 (2)	0.77694 (8)	0.0696 (5)
O2	0.6406 (2)	−0.08033 (19)	0.77500 (8)	0.0702 (5)
O3	0.7525 (2)	0.34032 (17)	0.89517 (10)	0.0685 (5)
O4	0.36103 (19)	0.42442 (18)	0.88546 (8)	0.0636 (5)
O5	0.5791 (3)	0.2410 (2)	1.02766 (10)	0.0887 (7)
N1	0.6850 (2)	0.03196 (17)	0.87461 (8)	0.0500 (4)
N2	0.5241 (2)	0.4359 (2)	0.89484 (10)	0.0581 (5)
C1	0.8659 (2)	0.0746 (2)	0.78344 (10)	0.0515 (5)
C2	0.9197 (3)	0.0215 (3)	0.73297 (13)	0.0733 (8)
H2	0.8590	−0.0352	0.7093	0.088*
C3	1.0668 (4)	0.0543 (4)	0.71811 (17)	0.0957 (11)
H3	1.1061	0.0188	0.6845	0.115*
C4	1.1538 (3)	0.1389 (3)	0.75290 (16)	0.0841 (9)
H4	1.2520	0.1606	0.7426	0.101*
C5	1.0981 (3)	0.1920 (3)	0.80265 (15)	0.0694 (7)
H5	1.1588	0.2494	0.8258	0.083*
C6	0.9522 (3)	0.1609 (2)	0.81871 (12)	0.0602 (6)
H6	0.9133	0.1971	0.8523	0.072*
C7	0.6276 (2)	0.1142 (2)	0.91567 (10)	0.0484 (5)
C8	0.6784 (3)	0.0778 (2)	0.97433 (10)	0.0508 (5)
C9	0.7702 (3)	−0.0301 (2)	0.97205 (10)	0.0500 (5)
C10	0.8521 (3)	−0.1040 (3)	1.01676 (12)	0.0647 (7)
H10	0.8514	−0.0882	1.0587	0.078*
C11	0.9338 (4)	−0.2009 (3)	0.99756 (16)	0.0754 (8)
H11	0.9901	−0.2504	1.0269	0.090*
C12	0.9333 (4)	−0.2257 (3)	0.93565 (16)	0.0764 (8)
H12	0.9885	−0.2926	0.9242	0.092*
C13	0.8548 (3)	−0.1556 (2)	0.89043 (14)	0.0668 (7)
H13	0.8556	−0.1728	0.8486	0.080*
C14	0.7736 (3)	−0.0572 (2)	0.90994 (11)	0.0515 (5)
C15	0.5211 (3)	0.2171 (2)	0.89660 (11)	0.0553 (5)
H15A	0.4437	0.2243	0.9253	0.066*
H15B	0.4659	0.2011	0.8558	0.066*
C16	0.6103 (3)	0.3346 (2)	0.89525 (10)	0.0524 (5)
C17	0.5823 (4)	0.5537 (3)	0.88116 (14)	0.0696 (7)
H17A	0.6936	0.5570	0.8936	0.104*
H17B	0.5312	0.6139	0.9034	0.104*
H17C	0.5610	0.5689	0.8375	0.104*
C18	0.2965 (4)	0.4541 (3)	0.94111 (15)	0.0785 (8)
H18A	0.3349	0.3983	0.9732	0.118*
H18B	0.1841	0.4495	0.9338	0.118*
H18C	0.3273	0.5346	0.9537	0.118*
C19	0.6408 (3)	0.1433 (3)	1.02879 (12)	0.0629 (6)
O6	0.6834 (2)	0.0827 (2)	1.08088 (8)	0.0821 (6)
C20	0.6451 (4)	0.1324 (5)	1.13690 (14)	0.1112 (13)
H20A	0.6224	0.0677	1.1645	0.133*	0.635 (6)
H20B	0.5515	0.1816	1.1284	0.133*	0.635 (6)
H20C	0.5409	0.1042	1.1426	0.133*	0.365 (6)
H20D	0.6384	0.2193	1.1316	0.133*	0.365 (6)
C21	0.7741 (6)	0.2069 (7)	1.1677 (3)	0.1115 (15)	0.635 (6)
H21A	0.8666	0.1582	1.1767	0.167*	0.635 (6)
H21B	0.7445	0.2389	1.2056	0.167*	0.635 (6)
H21C	0.7952	0.2722	1.1409	0.167*	0.635 (6)
C21A	0.7493 (10)	0.1083 (14)	1.1950 (3)	0.1106 (15)	0.365 (6)
H21D	0.7271	0.0296	1.2102	0.166*	0.365 (6)
H21E	0.7315	0.1680	1.2254	0.166*	0.365 (6)
H21F	0.8568	0.1118	1.1872	0.166*	0.365 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0435 (3)	0.0740 (4)	0.0426 (3)	−0.0057 (2)	0.0057 (2)	−0.0026 (2)
O1	0.0498 (9)	0.1027 (14)	0.0557 (9)	0.0104 (9)	0.0048 (7)	0.0120 (9)
O2	0.0692 (11)	0.0873 (13)	0.0553 (10)	−0.0237 (10)	0.0127 (8)	−0.0188 (9)
O3	0.0493 (9)	0.0661 (11)	0.0919 (13)	0.0024 (8)	0.0161 (8)	−0.0005 (10)
O4	0.0513 (9)	0.0826 (12)	0.0564 (9)	0.0145 (8)	0.0052 (7)	−0.0038 (8)
O5	0.1006 (16)	0.0973 (17)	0.0711 (13)	0.0049 (13)	0.0215 (11)	−0.0281 (12)
N1	0.0524 (10)	0.0554 (11)	0.0425 (9)	0.0009 (8)	0.0065 (7)	−0.0044 (8)
N2	0.0512 (10)	0.0622 (12)	0.0624 (12)	0.0070 (9)	0.0126 (9)	0.0021 (9)
C1	0.0411 (10)	0.0663 (14)	0.0475 (11)	−0.0022 (9)	0.0073 (8)	0.0010 (10)
C2	0.0582 (14)	0.100 (2)	0.0646 (15)	−0.0152 (14)	0.0181 (12)	−0.0212 (15)
C3	0.0676 (18)	0.140 (3)	0.086 (2)	−0.015 (2)	0.0361 (16)	−0.026 (2)
C4	0.0518 (14)	0.110 (3)	0.093 (2)	−0.0117 (15)	0.0209 (14)	0.0050 (19)
C5	0.0463 (12)	0.0724 (17)	0.0877 (19)	−0.0074 (11)	0.0009 (12)	−0.0014 (14)
C6	0.0494 (12)	0.0692 (15)	0.0617 (14)	−0.0006 (10)	0.0059 (10)	−0.0083 (11)
C7	0.0442 (10)	0.0533 (12)	0.0487 (11)	−0.0063 (9)	0.0099 (8)	−0.0046 (9)
C8	0.0495 (11)	0.0593 (13)	0.0441 (10)	−0.0119 (9)	0.0079 (8)	−0.0049 (9)
C9	0.0477 (10)	0.0534 (12)	0.0486 (11)	−0.0140 (9)	0.0045 (8)	0.0002 (9)
C10	0.0635 (14)	0.0711 (16)	0.0574 (13)	−0.0178 (12)	−0.0003 (11)	0.0120 (12)
C11	0.0720 (17)	0.0644 (17)	0.086 (2)	−0.0079 (13)	−0.0068 (14)	0.0207 (15)
C12	0.0746 (18)	0.0573 (15)	0.096 (2)	0.0052 (13)	0.0070 (15)	0.0031 (15)
C13	0.0689 (15)	0.0629 (15)	0.0688 (16)	0.0048 (12)	0.0093 (12)	−0.0071 (12)
C14	0.0495 (11)	0.0527 (12)	0.0522 (12)	−0.0051 (9)	0.0052 (9)	0.0000 (9)
C15	0.0435 (10)	0.0647 (14)	0.0580 (13)	0.0024 (10)	0.0067 (9)	−0.0059 (11)
C16	0.0504 (11)	0.0612 (13)	0.0462 (11)	0.0039 (10)	0.0080 (8)	−0.0028 (10)
C17	0.0807 (18)	0.0645 (16)	0.0678 (16)	0.0088 (13)	0.0265 (13)	0.0075 (12)
C18	0.0718 (17)	0.091 (2)	0.0787 (19)	0.0057 (15)	0.0315 (14)	−0.0056 (16)
C19	0.0539 (13)	0.0821 (18)	0.0542 (13)	−0.0131 (12)	0.0123 (10)	−0.0155 (12)
O6	0.0712 (12)	0.1331 (19)	0.0432 (9)	−0.0085 (12)	0.0115 (8)	−0.0107 (10)
C20	0.0693 (16)	0.209 (4)	0.0573 (15)	0.010 (2)	0.0169 (12)	−0.032 (2)
C21	0.0722 (19)	0.205 (4)	0.0585 (18)	0.007 (2)	0.0138 (15)	−0.036 (2)
C21A	0.071 (2)	0.206 (4)	0.057 (2)	0.008 (2)	0.0164 (17)	−0.034 (2)

Geometric parameters (Å, º) top

S1—O2	1.412 (2)	C10—H10	0.9300
S1—O1	1.415 (2)	C11—C12	1.373 (5)
S1—N1	1.6732 (19)	C11—H11	0.9300
S1—C1	1.751 (2)	C12—C13	1.364 (4)
O3—C16	1.222 (3)	C12—H12	0.9300
O4—N2	1.395 (3)	C13—C14	1.388 (4)
O4—C18	1.430 (3)	C13—H13	0.9300
O5—C19	1.204 (4)	C15—C16	1.513 (3)
N1—C7	1.407 (3)	C15—H15A	0.9700
N1—C14	1.414 (3)	C15—H15B	0.9700
N2—C16	1.343 (3)	C17—H17A	0.9600
N2—C17	1.442 (4)	C17—H17B	0.9600
C1—C2	1.374 (4)	C17—H17C	0.9600
C1—C6	1.383 (3)	C18—H18A	0.9600
C2—C3	1.390 (4)	C18—H18B	0.9600
C2—H2	0.9300	C18—H18C	0.9600
C3—C4	1.366 (5)	C19—O6	1.328 (4)
C3—H3	0.9300	O6—C20	1.412 (3)
C4—C5	1.368 (5)	C20—C21	1.474 (3)
C4—H4	0.9300	C20—C21A	1.479 (3)
C5—C6	1.385 (4)	C20—H20A	0.9700
C5—H5	0.9300	C20—H20B	0.9700
C6—H6	0.9300	C20—H20C	0.9700
C7—C8	1.358 (3)	C20—H20D	0.9700
C7—C15	1.487 (3)	C21—H21A	0.9600
C8—C9	1.435 (3)	C21—H21B	0.9600
C8—C19	1.458 (3)	C21—H21C	0.9600
C9—C14	1.387 (3)	C21A—H21D	0.9600
C9—C10	1.393 (3)	C21A—H21E	0.9600
C10—C11	1.375 (5)	C21A—H21F	0.9600

O2—S1—O1	119.21 (13)	C14—C13—H13	121.7
O2—S1—N1	107.07 (11)	C9—C14—C13	122.6 (2)
O1—S1—N1	107.15 (10)	C9—C14—N1	107.6 (2)
O2—S1—C1	108.50 (12)	C13—C14—N1	129.7 (2)
O1—S1—C1	109.49 (12)	C7—C15—C16	111.70 (18)
N1—S1—C1	104.39 (10)	C7—C15—H15A	109.3
N2—O4—C18	110.0 (2)	C16—C15—H15A	109.3
C7—N1—C14	108.36 (18)	C7—C15—H15B	109.3
C7—N1—S1	129.40 (16)	C16—C15—H15B	109.3
C14—N1—S1	121.93 (15)	H15A—C15—H15B	107.9
C16—N2—O4	117.8 (2)	O3—C16—N2	120.4 (2)
C16—N2—C17	123.6 (2)	O3—C16—C15	123.5 (2)
O4—N2—C17	114.8 (2)	N2—C16—C15	116.1 (2)
C2—C1—C6	121.9 (2)	N2—C17—H17A	109.5
C2—C1—S1	116.83 (19)	N2—C17—H17B	109.5
C6—C1—S1	121.00 (18)	H17A—C17—H17B	109.5
C1—C2—C3	118.6 (3)	N2—C17—H17C	109.5
C1—C2—H2	120.7	H17A—C17—H17C	109.5
C3—C2—H2	120.7	H17B—C17—H17C	109.5
C4—C3—C2	120.0 (3)	O4—C18—H18A	109.5
C4—C3—H3	120.0	O4—C18—H18B	109.5
C2—C3—H3	120.0	H18A—C18—H18B	109.5
C3—C4—C5	120.8 (3)	O4—C18—H18C	109.5
C3—C4—H4	119.6	H18A—C18—H18C	109.5
C5—C4—H4	119.6	H18B—C18—H18C	109.5
C4—C5—C6	120.5 (3)	O5—C19—O6	123.1 (3)
C4—C5—H5	119.8	O5—C19—C8	124.9 (3)
C6—C5—H5	119.8	O6—C19—C8	112.1 (3)
C1—C6—C5	118.1 (2)	C19—O6—C20	118.0 (3)
C1—C6—H6	120.9	O6—C20—C21	111.7 (3)
C5—C6—H6	120.9	O6—C20—C21A	119.1 (5)
C8—C7—N1	107.8 (2)	C21—C20—C21A	51.1 (6)
C8—C7—C15	127.3 (2)	O6—C20—H20A	109.3
N1—C7—C15	124.8 (2)	C21—C20—H20A	109.3
C7—C8—C9	109.2 (2)	O6—C20—H20B	109.3
C7—C8—C19	122.5 (2)	C21—C20—H20B	109.3
C9—C8—C19	128.3 (2)	H20A—C20—H20B	108.0
C14—C9—C10	118.8 (2)	O6—C20—H20C	107.5
C14—C9—C8	106.96 (19)	C21A—C20—H20C	107.5
C10—C9—C8	134.2 (2)	O6—C20—H20D	107.5
C11—C10—C9	118.7 (3)	C21A—C20—H20D	107.5
C11—C10—H10	120.7	H20C—C20—H20D	107.0
C9—C10—H10	120.7	C20—C21—H21A	109.5
C12—C11—C10	120.9 (3)	C20—C21—H21B	109.5
C12—C11—H11	119.6	C20—C21—H21C	109.5
C10—C11—H11	119.6	C20—C21A—H21D	109.5
C13—C12—C11	122.3 (3)	C20—C21A—H21E	109.5
C13—C12—H12	118.9	H21D—C21A—H21E	109.5
C11—C12—H12	118.9	C20—C21A—H21F	109.5
C12—C13—C14	116.7 (3)	H21D—C21A—H21F	109.5
C12—C13—H13	121.7	H21E—C21A—H21F	109.5

O2—S1—N1—C7	−138.9 (2)	C19—C8—C9—C10	−1.3 (4)
O1—S1—N1—C7	−9.9 (2)	C14—C9—C10—C11	0.3 (3)
C1—S1—N1—C7	106.2 (2)	C8—C9—C10—C11	−177.9 (2)
O2—S1—N1—C14	48.3 (2)	C9—C10—C11—C12	−0.9 (4)
O1—S1—N1—C14	177.31 (18)	C10—C11—C12—C13	0.9 (5)
C1—S1—N1—C14	−66.6 (2)	C11—C12—C13—C14	−0.3 (4)
C18—O4—N2—C16	111.0 (3)	C10—C9—C14—C13	0.3 (3)
C18—O4—N2—C17	−90.2 (3)	C8—C9—C14—C13	178.9 (2)
O2—S1—C1—C2	29.4 (3)	C10—C9—C14—N1	−178.86 (19)
O1—S1—C1—C2	−102.2 (2)	C8—C9—C14—N1	−0.3 (2)
N1—S1—C1—C2	143.3 (2)	C12—C13—C14—C9	−0.3 (4)
O2—S1—C1—C6	−155.9 (2)	C12—C13—C14—N1	178.7 (3)
O1—S1—C1—C6	72.4 (2)	C7—N1—C14—C9	0.2 (2)
N1—S1—C1—C6	−42.0 (2)	S1—N1—C14—C9	174.29 (15)
C6—C1—C2—C3	1.4 (5)	C7—N1—C14—C13	−178.9 (2)
S1—C1—C2—C3	176.0 (3)	S1—N1—C14—C13	−4.8 (3)
C1—C2—C3—C4	−0.8 (6)	C8—C7—C15—C16	85.8 (3)
C2—C3—C4—C5	0.2 (6)	N1—C7—C15—C16	−98.8 (2)
C3—C4—C5—C6	0.0 (5)	O4—N2—C16—O3	170.5 (2)
C2—C1—C6—C5	−1.2 (4)	C17—N2—C16—O3	13.6 (4)
S1—C1—C6—C5	−175.6 (2)	O4—N2—C16—C15	−10.3 (3)
C4—C5—C6—C1	0.5 (4)	C17—N2—C16—C15	−167.1 (2)
C14—N1—C7—C8	0.0 (2)	C7—C15—C16—O3	16.2 (3)
S1—N1—C7—C8	−173.54 (16)	C7—C15—C16—N2	−163.0 (2)
C14—N1—C7—C15	−176.2 (2)	C7—C8—C19—O5	−9.2 (4)
S1—N1—C7—C15	10.3 (3)	C9—C8—C19—O5	170.6 (3)
N1—C7—C8—C9	−0.2 (2)	C7—C8—C19—O6	171.1 (2)
C15—C7—C8—C9	175.9 (2)	C9—C8—C19—O6	−9.1 (3)
N1—C7—C8—C19	179.7 (2)	O5—C19—O6—C20	4.1 (4)
C15—C7—C8—C19	−4.3 (4)	C8—C19—O6—C20	−176.2 (2)
C7—C8—C9—C14	0.3 (2)	C19—O6—C20—C21	−93.0 (5)
C19—C8—C9—C14	−179.6 (2)	C19—O6—C20—C21A	−149.5 (7)
C7—C8—C9—C10	178.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.54	2.896 (3)	103
C6—H6···O3	0.93	2.37	3.218 (3)	152
C10—H10···O6	0.93	2.46	2.969 (4)	114
C13—H13···O2	0.93	2.51	3.039 (4)	117
C15—H15A···O5	0.97	2.39	2.844 (3)	108
C15—H15B···O1	0.97	2.17	2.847 (3)	126
C17—H17B···O5ⁱ	0.96	2.47	3.420 (3)	173
C20—H20C···N1ⁱⁱ	0.97	2.45	3.351 (4)	155
C20—H20C···O2ⁱⁱ	0.97	2.53	3.343 (4)	142
C21A—H21F···Cgⁱⁱⁱ	0.96	2.80	3.196 (13)	105

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂N₂O₆S
M_r	430.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.5827 (3), 11.0783 (5), 21.7433 (8)
β (°)	97.091 (2)
V (Å³)	2051.58 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker KappaAPEX2 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.914, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	29808, 7666, 3947
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.764

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.238, 1.04
No. of reflections	7666
No. of parameters	285
No. of restraints	20
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.62

Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.54	2.896 (3)	103
C6—H6···O3	0.93	2.37	3.218 (3)	152
C10—H10···O6	0.93	2.46	2.969 (4)	114
C13—H13···O2	0.93	2.51	3.039 (4)	117
C15—H15A···O5	0.97	2.39	2.844 (3)	108
C15—H15B···O1	0.97	2.17	2.847 (3)	126
C17—H17B···O5ⁱ	0.96	2.47	3.420 (3)	173
C20—H20C···N1ⁱⁱ	0.97	2.45	3.351 (4)	155
C20—H20C···O2ⁱⁱ	0.97	2.53	3.343 (4)	142
C21A—H21F···Cgⁱⁱⁱ	0.96	2.80	3.196 (13)	105

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

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

References

Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o4724. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o392. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hendi, S. & Basangoudar, L. D. (1981). Indian J. Chem. 208, 285–288. Google Scholar
Kolocouris, N., Foscolos, G. B., Kolocouris, A., Marakos, P., Pouli, N., Fytas, G., Ikeda, S. & De Clercq, E. (1994). J. Med. Chem. 37, 2896–2902. CrossRef CAS PubMed Web of Science Google Scholar
Merck (1973). French Patent 2 163 554. Google Scholar
Merck (1974). Chem. Abstr. 80, 27298. Google Scholar
Shaaban, M. A., Ghoneim, K. M. & Khalifa, M. (1977). Pharmazie, 32, 90–92. CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Uchida, M., Chihiro, M., Morita, S., Kanbe, T., Yamashita, H., Yamasaki, K., Yabuuchi, Y. & Nakagawa, K. (1989). Chem. Pharm. Bull. (Tokyo), 37, 2109–2116. CrossRef CAS PubMed Web of Science Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 2-[(N-meth­­oxy-N-methyl­carbamo­yl)meth­yl]-1-(phenyl­sulfon­yl)-1H-indole-3-carboxyl­ate

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Experimental

Crystal data

Data collection

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organic compounds

Ethyl 2-[(N-methoxy-N-methylcarbamoyl)methyl]-1-(phenylsulfonyl)-1H-indole-3-carboxylate