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organic compounds
Ethyl 2-[(N-methoxy-N-methylcarbamoyl)methyl]-1-(phenylsulfonyl)-1H-indole-3-carboxylate
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
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 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
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell 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
10.1107/S1600536808014979/is2294sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808014979/is2294Isup2.hkl
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
(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.H atoms were positioned geometrically (C—H = 0.93 – 0.97 Å) and refined using riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The site occupancy factors for disordered C atom was refined as C21 = 0.635 (6) and C21A = 0.365 (6) during anisotropic
The bond distances C20—C21 and C20—C21A were restrained to be 1.5 (3) Å and anisotropic displacement parameters of atoms C20, C21 and C21A were refined with a similar displacement restraint (SIMU) in the final cycles of refinement.Data collection: APEX2 (Bruker, 2004); cell
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).C21H22N2O6S | F(000) = 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 = 2.4–29.8° |
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 |
Bruker KappaAPEX2 diffractometer | 7666 independent reflections |
Radiation source: fine-focus sealed tube | 3947 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω and ϕ scans | θmax = 32.9°, θmin = 1.9° |
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 | 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(Fo2) + (0.1138P)2 + 0.5762P] where P = (Fo2 + 2Fc2)/3 |
7666 reflections | (Δ/σ)max < 0.001 |
285 parameters | Δρmax = 0.82 e Å−3 |
20 restraints | Δρmin = −0.62 e Å−3 |
C21H22N2O6S | V = 2051.58 (14) Å3 |
Mr = 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)° |
Bruker KappaAPEX2 diffractometer | 7666 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3947 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.961 | Rint = 0.029 |
29808 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | 20 restraints |
wR(F2) = 0.238 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.82 e Å−3 |
7666 reflections | Δρmin = −0.62 e Å−3 |
285 parameters |
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 |
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 |
Mr | 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) |
Tmin, Tmax | 0.914, 0.961 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29808, 7666, 3947 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.82, −0.62 |
Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).
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
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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).