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organic compounds
Trimethyl 1-(2-methyl-1-phenylsulfonyl-1H-indol-3-yl)propane-1,2,3-tricarboxylate
aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600025, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600025, India.
*Correspondence e-mail: mnpsy2004@yahoo.com
In the title compound, C24H25NO8S, the indole unit is planar and makes a dihedral angle of 79.73 (11)° with the phenyl ring of the sulfonyl substituent. The molecules in the are stabilized by C—H⋯O and C—H⋯π intermolecular interactions in addition to van der Waals forces.
Related literature
For the bological activity and applications of indole derivatives, see: Ho et al. (1986); Rajeswaran et al. (1999
); Stevenson et al. (2000
). For the Thorpe-Ingold effect, see: Bassindale (1984
). For bond-length data, see: Allen et al. (1987
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004
); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP (Farrugia, 1997
); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003
).
Supporting information
10.1107/S1600536808043286/bt2840sup1.cif
contains datablocks I, rsb357. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808043286/bt2840Isup2.hkl
To a stirred solution of dimethyl 2-(2-methyl-1-(phenylsulfonyl)-1H-indol-3-yl) maleate (0.4 g, 0.96 mmol) in dry DMF (1.5 ml), dimethyl acetamide dimethyl acetal (257 mg, 1.9 mmol) was added. Reaction mixture was heated to 110° C for 3hrs under nitrogen atmosphere. Then it was poured to 2% aqueous HCl (15 ml) solution and extracted with CHCl3. Organic layer was dried over Na2SO4 and evaporated. The crude compound was recrystallized from methanol.
H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(Cmethyl) and 1.2Ueq(C). The components of the anisotropic displacement parameters of C11 and C12 in the direction of the bond between them were restrained to be equal within an effective standard deviation of 0.001.
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).C24H25NO8S | F(000) = 1024 |
Mr = 487.51 | Dx = 1.365 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5592 reflections |
a = 11.0975 (3) Å | θ = 2.3–27.8° |
b = 9.8255 (3) Å | µ = 0.19 mm−1 |
c = 22.0027 (6) Å | T = 293 K |
β = 98.605 (2)° | Needle, colourless |
V = 2372.13 (12) Å3 | 0.40 × 0.30 × 0.15 mm |
Z = 4 |
Bruker KAPPA APEXII diffractometer | 5592 independent reflections |
Radiation source: fine-focus sealed tube | 3885 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω and ϕ scan | θmax = 27.8°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −14→14 |
Tmin = 0.835, Tmax = 0.973 | k = −12→12 |
25507 measured reflections | l = −28→28 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0566P)2 + 0.8871P] where P = (Fo2 + 2Fc2)/3 |
5592 reflections | (Δ/σ)max < 0.001 |
308 parameters | Δρmax = 0.25 e Å−3 |
1 restraint | Δρmin = −0.27 e Å−3 |
C24H25NO8S | V = 2372.13 (12) Å3 |
Mr = 487.51 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.0975 (3) Å | µ = 0.19 mm−1 |
b = 9.8255 (3) Å | T = 293 K |
c = 22.0027 (6) Å | 0.40 × 0.30 × 0.15 mm |
β = 98.605 (2)° |
Bruker KAPPA APEXII diffractometer | 5592 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 3885 reflections with I > 2σ(I) |
Tmin = 0.835, Tmax = 0.973 | Rint = 0.027 |
25507 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 1 restraint |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.25 e Å−3 |
5592 reflections | Δρmin = −0.27 e Å−3 |
308 parameters |
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 | ||
C2 | 0.20679 (17) | 0.1921 (2) | 0.08315 (8) | 0.0503 (4) | |
C3 | 0.19449 (15) | 0.11193 (18) | 0.13178 (8) | 0.0433 (4) | |
C4 | 0.29851 (15) | 0.13314 (17) | 0.17830 (8) | 0.0418 (4) | |
C5 | 0.37387 (16) | 0.22937 (18) | 0.15615 (8) | 0.0433 (4) | |
C6 | 0.48157 (17) | 0.2729 (2) | 0.19067 (9) | 0.0539 (5) | |
H6 | 0.5319 | 0.3352 | 0.1750 | 0.065* | |
C7 | 0.51138 (19) | 0.2207 (2) | 0.24880 (10) | 0.0604 (5) | |
H7 | 0.5826 | 0.2495 | 0.2731 | 0.072* | |
C8 | 0.4380 (2) | 0.1263 (2) | 0.27211 (9) | 0.0600 (5) | |
H8 | 0.4602 | 0.0934 | 0.3118 | 0.072* | |
C9 | 0.33297 (17) | 0.0807 (2) | 0.23731 (8) | 0.0508 (4) | |
H9 | 0.2851 | 0.0154 | 0.2529 | 0.061* | |
C10 | 0.46121 (19) | 0.2643 (2) | 0.00851 (9) | 0.0540 (5) | |
C11 | 0.4134 (3) | 0.2268 (3) | −0.04999 (10) | 0.0781 (7) | |
H11 | 0.3367 | 0.2565 | −0.0680 | 0.094* | |
C12 | 0.4830 (4) | 0.1428 (4) | −0.08160 (13) | 0.1017 (10) | |
H12 | 0.4531 | 0.1172 | −0.1217 | 0.122* | |
C13 | 0.5936 (3) | 0.0974 (3) | −0.05521 (16) | 0.0975 (9) | |
H13 | 0.6381 | 0.0395 | −0.0769 | 0.117* | |
C14 | 0.6397 (3) | 0.1361 (3) | 0.00258 (16) | 0.0978 (9) | |
H14 | 0.7161 | 0.1052 | 0.0204 | 0.117* | |
C15 | 0.5745 (2) | 0.2208 (3) | 0.03505 (12) | 0.0742 (6) | |
H15 | 0.6067 | 0.2483 | 0.0746 | 0.089* | |
C16 | 0.1242 (2) | 0.2032 (3) | 0.02344 (10) | 0.0815 (7) | |
H16A | 0.0582 | 0.1397 | 0.0228 | 0.122* | |
H16B | 0.1688 | 0.1831 | −0.0096 | 0.122* | |
H16C | 0.0921 | 0.2940 | 0.0187 | 0.122* | |
C17 | 0.08720 (16) | 0.02092 (19) | 0.13676 (9) | 0.0485 (4) | |
H17 | 0.0281 | 0.0318 | 0.0993 | 0.058* | |
C18 | 0.12894 (18) | −0.1261 (2) | 0.14060 (10) | 0.0561 (5) | |
C19 | 0.1671 (3) | −0.3195 (3) | 0.08387 (17) | 0.1092 (11) | |
H19A | 0.1599 | −0.3499 | 0.0420 | 0.164* | |
H19B | 0.1187 | −0.3768 | 0.1060 | 0.164* | |
H19C | 0.2508 | −0.3241 | 0.1026 | 0.164* | |
C20 | 0.02316 (16) | 0.0556 (2) | 0.19188 (9) | 0.0493 (4) | |
H20 | 0.0750 | 0.0199 | 0.2284 | 0.059* | |
C21 | −0.09641 (18) | −0.0204 (2) | 0.18689 (11) | 0.0588 (5) | |
C22 | −0.2746 (2) | −0.0409 (3) | 0.23308 (17) | 0.1057 (11) | |
H22A | −0.3099 | −0.0019 | 0.2663 | 0.159* | |
H22B | −0.2635 | −0.1370 | 0.2397 | 0.159* | |
H22C | −0.3278 | −0.0257 | 0.1951 | 0.159* | |
C23 | 0.00794 (17) | 0.2075 (2) | 0.20302 (9) | 0.0510 (4) | |
H23A | −0.0237 | 0.2193 | 0.2415 | 0.061* | |
H23B | 0.0876 | 0.2503 | 0.2076 | 0.061* | |
C24 | −0.0740 (2) | 0.2789 (2) | 0.15365 (10) | 0.0601 (5) | |
C25 | −0.1514 (3) | 0.4926 (3) | 0.11907 (15) | 0.1146 (12) | |
H25A | −0.1432 | 0.5867 | 0.1308 | 0.172* | |
H25B | −0.2346 | 0.4647 | 0.1181 | 0.172* | |
H25C | −0.1283 | 0.4809 | 0.0791 | 0.172* | |
N1 | 0.31622 (14) | 0.26844 (17) | 0.09733 (7) | 0.0501 (4) | |
O1 | 0.45912 (16) | 0.45716 (15) | 0.08815 (7) | 0.0753 (5) | |
O2 | 0.27957 (16) | 0.42841 (17) | 0.00952 (7) | 0.0764 (5) | |
O3 | 0.16646 (16) | −0.18474 (16) | 0.18733 (8) | 0.0770 (5) | |
O4 | 0.12431 (16) | −0.17999 (17) | 0.08525 (8) | 0.0783 (5) | |
O5 | −0.12856 (16) | −0.1090 (2) | 0.15146 (9) | 0.0887 (6) | |
O6 | −0.15876 (13) | 0.02166 (17) | 0.23022 (8) | 0.0749 (5) | |
O7 | −0.13414 (19) | 0.2252 (2) | 0.11119 (9) | 0.1051 (7) | |
O8 | −0.07383 (19) | 0.41121 (17) | 0.16292 (8) | 0.0862 (5) | |
S1 | 0.37776 (5) | 0.37135 (5) | 0.04991 (2) | 0.05603 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0531 (10) | 0.0538 (11) | 0.0440 (9) | 0.0028 (8) | 0.0067 (8) | −0.0011 (8) |
C3 | 0.0434 (9) | 0.0440 (9) | 0.0427 (9) | 0.0047 (7) | 0.0073 (7) | −0.0023 (7) |
C4 | 0.0428 (9) | 0.0397 (9) | 0.0436 (9) | 0.0063 (7) | 0.0084 (7) | −0.0009 (7) |
C5 | 0.0472 (9) | 0.0412 (9) | 0.0422 (9) | 0.0056 (7) | 0.0090 (7) | −0.0009 (7) |
C6 | 0.0508 (10) | 0.0504 (11) | 0.0605 (11) | −0.0032 (8) | 0.0086 (9) | −0.0026 (9) |
C7 | 0.0528 (11) | 0.0553 (12) | 0.0676 (13) | 0.0011 (9) | −0.0090 (9) | −0.0034 (10) |
C8 | 0.0663 (12) | 0.0561 (12) | 0.0525 (11) | 0.0088 (10) | −0.0078 (9) | 0.0088 (9) |
C9 | 0.0538 (10) | 0.0478 (10) | 0.0500 (10) | 0.0038 (8) | 0.0050 (8) | 0.0081 (8) |
C10 | 0.0688 (12) | 0.0471 (10) | 0.0494 (10) | −0.0065 (9) | 0.0200 (9) | 0.0035 (8) |
C11 | 0.0970 (18) | 0.0868 (18) | 0.0511 (12) | 0.0039 (14) | 0.0131 (11) | −0.0042 (11) |
C12 | 0.131 (3) | 0.112 (2) | 0.0685 (16) | −0.0052 (19) | 0.0349 (17) | −0.0295 (16) |
C13 | 0.108 (2) | 0.086 (2) | 0.113 (2) | −0.0005 (17) | 0.060 (2) | −0.0206 (18) |
C14 | 0.0734 (17) | 0.112 (2) | 0.115 (2) | 0.0110 (16) | 0.0366 (17) | −0.009 (2) |
C15 | 0.0618 (13) | 0.0907 (18) | 0.0722 (14) | −0.0026 (12) | 0.0165 (11) | −0.0093 (13) |
C16 | 0.0815 (16) | 0.107 (2) | 0.0499 (12) | −0.0113 (15) | −0.0089 (11) | 0.0143 (13) |
C17 | 0.0444 (9) | 0.0502 (10) | 0.0501 (10) | 0.0013 (8) | 0.0050 (8) | −0.0035 (8) |
C18 | 0.0487 (10) | 0.0503 (11) | 0.0705 (13) | −0.0022 (9) | 0.0124 (9) | −0.0050 (10) |
C19 | 0.117 (2) | 0.0646 (17) | 0.148 (3) | 0.0101 (16) | 0.027 (2) | −0.0415 (19) |
C20 | 0.0422 (9) | 0.0526 (11) | 0.0536 (10) | 0.0018 (8) | 0.0085 (8) | 0.0017 (8) |
C21 | 0.0488 (10) | 0.0526 (12) | 0.0760 (14) | 0.0018 (9) | 0.0121 (10) | 0.0042 (11) |
C22 | 0.0609 (14) | 0.092 (2) | 0.175 (3) | −0.0002 (14) | 0.0522 (18) | 0.017 (2) |
C23 | 0.0485 (10) | 0.0534 (11) | 0.0521 (10) | −0.0001 (8) | 0.0107 (8) | −0.0055 (9) |
C24 | 0.0615 (12) | 0.0592 (13) | 0.0586 (12) | 0.0057 (10) | 0.0053 (10) | −0.0031 (10) |
C25 | 0.156 (3) | 0.079 (2) | 0.099 (2) | 0.031 (2) | −0.010 (2) | 0.0267 (17) |
N1 | 0.0567 (9) | 0.0531 (9) | 0.0413 (8) | −0.0020 (7) | 0.0102 (7) | 0.0041 (7) |
O1 | 0.1135 (13) | 0.0496 (9) | 0.0662 (9) | −0.0231 (8) | 0.0248 (9) | −0.0078 (7) |
O2 | 0.0989 (12) | 0.0637 (10) | 0.0682 (9) | 0.0233 (9) | 0.0176 (9) | 0.0220 (8) |
O3 | 0.0903 (12) | 0.0548 (9) | 0.0878 (11) | 0.0109 (8) | 0.0190 (9) | 0.0118 (9) |
O4 | 0.0842 (11) | 0.0650 (10) | 0.0850 (11) | 0.0087 (8) | 0.0105 (9) | −0.0285 (9) |
O5 | 0.0715 (10) | 0.0827 (12) | 0.1152 (14) | −0.0247 (9) | 0.0244 (10) | −0.0281 (11) |
O6 | 0.0568 (8) | 0.0733 (10) | 0.1017 (12) | −0.0007 (7) | 0.0357 (8) | −0.0018 (9) |
O7 | 0.1096 (15) | 0.0845 (13) | 0.1019 (14) | 0.0232 (11) | −0.0467 (12) | −0.0187 (11) |
O8 | 0.1247 (15) | 0.0551 (9) | 0.0718 (10) | 0.0118 (10) | −0.0082 (10) | 0.0064 (8) |
S1 | 0.0792 (4) | 0.0419 (3) | 0.0498 (3) | 0.0007 (2) | 0.0190 (2) | 0.0046 (2) |
C2—C3 | 1.352 (3) | C17—C18 | 1.516 (3) |
C2—N1 | 1.421 (2) | C17—C20 | 1.533 (3) |
C2—C16 | 1.489 (3) | C17—H17 | 0.9800 |
C3—C4 | 1.439 (2) | C18—O3 | 1.198 (3) |
C3—C17 | 1.506 (3) | C18—O4 | 1.322 (3) |
C4—C9 | 1.396 (2) | C19—O4 | 1.452 (3) |
C4—C5 | 1.397 (2) | C19—H19A | 0.9600 |
C5—C6 | 1.384 (3) | C19—H19B | 0.9600 |
C5—N1 | 1.408 (2) | C19—H19C | 0.9600 |
C6—C7 | 1.372 (3) | C20—C21 | 1.512 (3) |
C6—H6 | 0.9300 | C20—C23 | 1.526 (3) |
C7—C8 | 1.382 (3) | C20—H20 | 0.9800 |
C7—H7 | 0.9300 | C21—O5 | 1.187 (3) |
C8—C9 | 1.371 (3) | C21—O6 | 1.325 (3) |
C8—H8 | 0.9300 | C22—O6 | 1.434 (3) |
C9—H9 | 0.9300 | C22—H22A | 0.9600 |
C10—C11 | 1.368 (3) | C22—H22B | 0.9600 |
C10—C15 | 1.373 (3) | C22—H22C | 0.9600 |
C10—S1 | 1.745 (2) | C23—C24 | 1.484 (3) |
C11—C12 | 1.386 (4) | C23—H23A | 0.9700 |
C11—H11 | 0.9300 | C23—H23B | 0.9700 |
C12—C13 | 1.353 (4) | C24—O7 | 1.188 (3) |
C12—H12 | 0.9300 | C24—O8 | 1.316 (3) |
C13—C14 | 1.352 (4) | C25—O8 | 1.436 (3) |
C13—H13 | 0.9300 | C25—H25A | 0.9600 |
C14—C15 | 1.371 (4) | C25—H25B | 0.9600 |
C14—H14 | 0.9300 | C25—H25C | 0.9600 |
C15—H15 | 0.9300 | N1—S1 | 1.6706 (16) |
C16—H16A | 0.9600 | O1—S1 | 1.4165 (16) |
C16—H16B | 0.9600 | O2—S1 | 1.4148 (16) |
C16—H16C | 0.9600 | ||
C3—C2—N1 | 108.53 (16) | C20—C17—H17 | 108.1 |
C3—C2—C16 | 128.23 (19) | O3—C18—O4 | 124.0 (2) |
N1—C2—C16 | 123.25 (18) | O3—C18—C17 | 124.8 (2) |
C2—C3—C4 | 108.26 (16) | O4—C18—C17 | 111.16 (19) |
C2—C3—C17 | 125.32 (16) | O4—C19—H19A | 109.5 |
C4—C3—C17 | 126.38 (16) | O4—C19—H19B | 109.5 |
C9—C4—C5 | 118.63 (16) | H19A—C19—H19B | 109.5 |
C9—C4—C3 | 133.41 (17) | O4—C19—H19C | 109.5 |
C5—C4—C3 | 107.95 (15) | H19A—C19—H19C | 109.5 |
C6—C5—C4 | 122.01 (17) | H19B—C19—H19C | 109.5 |
C6—C5—N1 | 131.02 (17) | C21—C20—C23 | 112.17 (16) |
C4—C5—N1 | 106.95 (15) | C21—C20—C17 | 109.78 (16) |
C7—C6—C5 | 117.66 (19) | C23—C20—C17 | 114.83 (16) |
C7—C6—H6 | 121.2 | C21—C20—H20 | 106.5 |
C5—C6—H6 | 121.2 | C23—C20—H20 | 106.5 |
C6—C7—C8 | 121.56 (19) | C17—C20—H20 | 106.5 |
C6—C7—H7 | 119.2 | O5—C21—O6 | 124.3 (2) |
C8—C7—H7 | 119.2 | O5—C21—C20 | 125.7 (2) |
C9—C8—C7 | 120.73 (18) | O6—C21—C20 | 109.94 (19) |
C9—C8—H8 | 119.6 | O6—C22—H22A | 109.5 |
C7—C8—H8 | 119.6 | O6—C22—H22B | 109.5 |
C8—C9—C4 | 119.37 (18) | H22A—C22—H22B | 109.5 |
C8—C9—H9 | 120.3 | O6—C22—H22C | 109.5 |
C4—C9—H9 | 120.3 | H22A—C22—H22C | 109.5 |
C11—C10—C15 | 121.2 (2) | H22B—C22—H22C | 109.5 |
C11—C10—S1 | 119.50 (18) | C24—C23—C20 | 114.51 (17) |
C15—C10—S1 | 119.32 (17) | C24—C23—H23A | 108.6 |
C10—C11—C12 | 117.8 (3) | C20—C23—H23A | 108.6 |
C10—C11—H11 | 121.1 | C24—C23—H23B | 108.6 |
C12—C11—H11 | 121.1 | C20—C23—H23B | 108.6 |
C13—C12—C11 | 121.3 (3) | H23A—C23—H23B | 107.6 |
C13—C12—H12 | 119.4 | O7—C24—O8 | 123.3 (2) |
C11—C12—H12 | 119.4 | O7—C24—C23 | 125.2 (2) |
C14—C13—C12 | 120.2 (3) | O8—C24—C23 | 111.51 (18) |
C14—C13—H13 | 119.9 | O8—C25—H25A | 109.5 |
C12—C13—H13 | 119.9 | O8—C25—H25B | 109.5 |
C13—C14—C15 | 120.4 (3) | H25A—C25—H25B | 109.5 |
C13—C14—H14 | 119.8 | O8—C25—H25C | 109.5 |
C15—C14—H14 | 119.8 | H25A—C25—H25C | 109.5 |
C14—C15—C10 | 119.2 (3) | H25B—C25—H25C | 109.5 |
C14—C15—H15 | 120.4 | C5—N1—C2 | 108.28 (15) |
C10—C15—H15 | 120.4 | C5—N1—S1 | 124.53 (13) |
C2—C16—H16A | 109.5 | C2—N1—S1 | 126.71 (13) |
C2—C16—H16B | 109.5 | C18—O4—C19 | 115.4 (2) |
H16A—C16—H16B | 109.5 | C21—O6—C22 | 117.8 (2) |
C2—C16—H16C | 109.5 | C24—O8—C25 | 117.3 (2) |
H16A—C16—H16C | 109.5 | O2—S1—O1 | 119.99 (11) |
H16B—C16—H16C | 109.5 | O2—S1—N1 | 106.49 (9) |
C3—C17—C18 | 109.37 (15) | O1—S1—N1 | 105.85 (8) |
C3—C17—C20 | 113.00 (15) | O2—S1—C10 | 109.26 (10) |
C18—C17—C20 | 109.98 (16) | O1—S1—C10 | 109.13 (10) |
C3—C17—H17 | 108.1 | N1—S1—C10 | 105.05 (9) |
C18—C17—H17 | 108.1 | ||
N1—C2—C3—C4 | −1.3 (2) | C3—C17—C20—C23 | 41.5 (2) |
C16—C2—C3—C4 | 178.3 (2) | C18—C17—C20—C23 | 164.05 (16) |
N1—C2—C3—C17 | 176.42 (16) | C23—C20—C21—O5 | 139.6 (2) |
C16—C2—C3—C17 | −4.0 (3) | C17—C20—C21—O5 | 10.7 (3) |
C2—C3—C4—C9 | 178.73 (19) | C23—C20—C21—O6 | −43.5 (2) |
C17—C3—C4—C9 | 1.1 (3) | C17—C20—C21—O6 | −172.46 (17) |
C2—C3—C4—C5 | 0.2 (2) | C21—C20—C23—C24 | −60.8 (2) |
C17—C3—C4—C5 | −177.43 (16) | C17—C20—C23—C24 | 65.5 (2) |
C9—C4—C5—C6 | 0.6 (3) | C20—C23—C24—O7 | 7.2 (3) |
C3—C4—C5—C6 | 179.38 (16) | C20—C23—C24—O8 | −173.73 (18) |
C9—C4—C5—N1 | −177.85 (15) | C6—C5—N1—C2 | −179.95 (19) |
C3—C4—C5—N1 | 0.92 (19) | C4—C5—N1—C2 | −1.68 (19) |
C4—C5—C6—C7 | −1.6 (3) | C6—C5—N1—S1 | 7.5 (3) |
N1—C5—C6—C7 | 176.41 (19) | C4—C5—N1—S1 | −174.21 (12) |
C5—C6—C7—C8 | 1.0 (3) | C3—C2—N1—C5 | 1.8 (2) |
C6—C7—C8—C9 | 0.6 (3) | C16—C2—N1—C5 | −177.8 (2) |
C7—C8—C9—C4 | −1.7 (3) | C3—C2—N1—S1 | 174.17 (14) |
C5—C4—C9—C8 | 1.1 (3) | C16—C2—N1—S1 | −5.4 (3) |
C3—C4—C9—C8 | −177.31 (19) | O3—C18—O4—C19 | 0.8 (3) |
C15—C10—C11—C12 | 0.2 (4) | C17—C18—O4—C19 | 177.7 (2) |
S1—C10—C11—C12 | 179.3 (2) | O5—C21—O6—C22 | −2.2 (4) |
C10—C11—C12—C13 | 1.1 (5) | C20—C21—O6—C22 | −179.2 (2) |
C11—C12—C13—C14 | −1.5 (5) | O7—C24—O8—C25 | 0.3 (4) |
C12—C13—C14—C15 | 0.5 (5) | C23—C24—O8—C25 | −178.8 (2) |
C13—C14—C15—C10 | 0.8 (5) | C5—N1—S1—O2 | −156.71 (15) |
C11—C10—C15—C14 | −1.2 (4) | C2—N1—S1—O2 | 32.14 (19) |
S1—C10—C15—C14 | 179.7 (2) | C5—N1—S1—O1 | −27.97 (18) |
C2—C3—C17—C18 | 116.4 (2) | C2—N1—S1—O1 | 160.89 (16) |
C4—C3—C17—C18 | −66.4 (2) | C5—N1—S1—C10 | 87.45 (16) |
C2—C3—C17—C20 | −120.8 (2) | C2—N1—S1—C10 | −83.70 (18) |
C4—C3—C17—C20 | 56.5 (2) | C11—C10—S1—O2 | −13.0 (2) |
C3—C17—C18—O3 | 88.7 (2) | C15—C10—S1—O2 | 166.18 (18) |
C20—C17—C18—O3 | −36.0 (3) | C11—C10—S1—O1 | −145.95 (18) |
C3—C17—C18—O4 | −88.3 (2) | C15—C10—S1—O1 | 33.2 (2) |
C20—C17—C18—O4 | 147.10 (17) | C11—C10—S1—N1 | 100.93 (19) |
C3—C17—C20—C21 | 169.00 (15) | C15—C10—S1—N1 | −79.91 (19) |
C18—C17—C20—C21 | −68.48 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23A···O3i | 0.97 | 2.57 | 3.476 (3) | 156 |
C13—H13···Cg1ii | 0.93 | 2.73 | 3.633 (3) | 163 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C24H25NO8S |
Mr | 487.51 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 11.0975 (3), 9.8255 (3), 22.0027 (6) |
β (°) | 98.605 (2) |
V (Å3) | 2372.13 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.40 × 0.30 × 0.15 |
Data collection | |
Diffractometer | Bruker KAPPA APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.835, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25507, 5592, 3885 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.656 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.135, 1.02 |
No. of reflections | 5592 |
No. of parameters | 308 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.27 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), ORTEP (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23A···O3i | 0.97 | 2.57 | 3.476 (3) | 155.8 |
C13—H13···Cg1ii | 0.93 | 2.73 | 3.633 (3) | 162.7 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, −y, −z. |
Acknowledgements
TK thanks Dr Babu Varghese, SAIF, IIT–Madras, Chennai, India, for his help with 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.
Indole derivatives are used as bioactive drugs (Stevenson et al., 2000) and they exibit anti-allergic, central nervous system depressant and muscle relaxant properties (Ho et al., 1986). Indoles also have been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999).
The bond lengths N1- C2 [1.421 (2) Å] and N1- C5 [1.408 (2) Å] are longer than the mean value of 1.355 (1) Å reported for the indole moiety (Allen et al., 1987). The S atom shows a distorted tetrahedral geometry, with O1—S1—O2 [119.99 (11)°] and N1—S1—C10 [105.05 (9)°] angles deviating from ideal tetrahedral values, are attributed to the Thorpe-Ingold effect (Bassindale, 1984). The indole ring is planar and the sulfonyl bound phenyl ring is almost perpendicular to the indole ring system, with a dihedral angle of 79.73 (11)°. The sum of bond angles around N1 (359.5°) indicates that N1 is in sp2 hybridization. The ester groups attached to the indole ring system assume extended conformation [C23- C24- O8- C25 = -178.8 (2)°; C20- C21- O6- C22 = -179.2 (2)° and C17- C18- O4- C19 = 177.7 (2)°].
The molecules in the crystal structure extend along the b axis via intermolecular C—H···O hydrogen bonds involving atoms C23 and O3 (-x,y + 1/2,- z + 1/2). Dimerization of the molecules occurs through C—H···π interactions [C13—H13 =0.93, H13···Cg1 = 2.7340, C13···Cg1 = 3.633 (3) Å and C13—H13···Cg1 = 162.73 °, where Cg1 is the centroid of the ring N1—C5].