Ethyl 2-[(N-meth-oxy-N-methyl-carbamo-yl)meth-yl]-1-(phenyl-sulfon-yl)-1H-indole-3-carboxyl-ate.

In the title compound, C(21)H(22)N(2)O(6)S, 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 intra-molecular C-H⋯O inter-actions and inter-molecular C-H⋯O, C-H⋯N and C-H⋯π inter-actions 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 = 430.47

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.238

S = 1.04

7666 reflections

285 parameters

20 restraints

H-atom parameters constrained

Δρmax = 0.82 e Å−3

Δρmin = −0.62 e Å−3

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.

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

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

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

C21H22N2O6S	F000 = 904
Mr = 430.47	Dx = 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 = 2.4–29.8º
b = 11.0783 (5) Å	µ = 0.20 mm−1
c = 21.7433 (8) Å	T = 295 (2) K
β = 97.091 (2)º	Block, colourless
V = 2051.58 (14) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker KappaAPEX2 diffractometer	7666 independent reflections
Radiation source: fine-focus sealed tube	3947 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
T = 295(2) K	θmax = 32.9º
ω and φ scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.914, Tmax = 0.961	k = −16→16
29808 measured reflections	l = −33→32

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H-atom parameters constrained
wR(F2) = 0.238	w = 1/[σ2(Fo2) + (0.1138P)2 + 0.5762P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
7666 reflections	Δρmax = 0.82 e Å−3
285 parameters	Δρmin = −0.62 e Å−3
20 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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

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) ; (ii) ; (iii) . Cg is the centroid of the C1–C6 phenyl ring.