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Acta Cryst. (2007). E63, o3673    [ doi:10.1107/S1600536807036987 ]

Methyl (2-methyl-1-phenylsulfonyl-1H-indol-3-yl)glyoxylate

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

Abstract top

In the title compound, C18H15NO5S, the phenyl ring makes a dihedral angle of 85.33 (5)° 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...[pi] interactions.

Comment top

The derivatives of pyrrolidine have been found to exhibit antifungal and antimicrobial activities (Amal Raj et al., 2003) and inhibit human immunodeficiency virus type-I (HIV-I) (Jiang et al., 2004).

The geometric parameters in the title compound, (I), agree with the reported values of similar structures (Palani et al., 2006; Senthil Kumar et al., 2006). The phenyl ring makes a dihedral angle of 85.33 (5)° with the indole ring system (Fig. 1). The five-membered N1/C7/C12/C13/C14 and six-membered C7—C12 rings in the indole group are planar, with a dihedral angle of 1.19 (5)° between these rings. The sum of the bond angles around N1 (359.9°) indicates that N1 is sp2-hybridized. The torsion angles O2—S1—N1—C14 and O1—S1—N1—C7 [−2.26 (14)° and 44.21 (12)°, 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 of (I) (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 Cg3) rings.

Related literature top

For related literature, see: Amal Raj et al. (2003); Jiang et al. (2004); Palani et al. (2006); Senthil Kumar et al. (2006). A similar phenylsulfonylindole compound with a nitro group has been reported (Kishbaugh et al., 2006).

Experimental top

To a solution of methyl 2-(2-methyl-1H-indole-3-yl)-2-oxo acetate (10 g, 43.0 mmol) in dry dichloromethane (80 ml) under nitrogen, triethylamine (8.3 ml, 59.9 mmol) followed by dimethyl amino pyridine (0.56 g, 4.6 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, poured over crushed ice and then extracted with dichloromethane (3 × 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.

Refinement top

H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å) and refined using riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

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 top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. A packing scheme of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.
Methyl (2-methyl-1-phenylsulfonyl-1H-indol-3-yl)glyoxylate top
Crystal data top
C18H15NO5SF000 = 744
Mr = 357.37Dx = 1.411 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8031 reflections
a = 9.7005 (3) Åθ = 2.2–31.5º
b = 12.9924 (4) ŵ = 0.22 mm−1
c = 13.4224 (3) ÅT = 295 (2) K
β = 96.189 (1)ºBlock, colourless
V = 1681.80 (8) Å30.20 × 0.16 × 0.16 mm
Z = 4
Data collection top
Bruker Kappa APEX II
diffractometer		5550 independent reflections
Radiation source: fine-focus sealed tube4082 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.024
T = 295(2) Kθmax = 31.5º
ω and φ scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→14
Tmin = 0.882, Tmax = 0.966k = −19→18
23482 measured reflectionsl = −19→19
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.132  w = 1/[σ2(Fo2) + (0.0649P)2 + 0.3886P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
5550 reflectionsΔρmax = 0.33 e Å−3
227 parametersΔρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C18H15NO5SV = 1681.80 (8) Å3
Mr = 357.37Z = 4
Monoclinic, P21/nMo Kα
a = 9.7005 (3) ŵ = 0.22 mm−1
b = 12.9924 (4) ÅT = 295 (2) K
c = 13.4224 (3) Å0.20 × 0.16 × 0.16 mm
β = 96.189 (1)º
Data collection top
Bruker Kappa APEX II
diffractometer		5550 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4082 reflections with I > 2σ(I)
Tmin = 0.882, Tmax = 0.966Rint = 0.024
23482 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043227 parameters
wR(F2) = 0.132H-atom parameters constrained
S = 1.04Δρmax = 0.33 e Å−3
5550 reflectionsΔρmin = −0.33 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.22348 (3)0.15223 (3)0.22741 (2)0.03990 (10)
O10.27574 (12)0.25315 (10)0.21547 (9)0.0561 (3)
O20.31128 (12)0.06594 (11)0.22066 (8)0.0573 (3)
O30.07775 (17)0.09577 (12)0.66431 (10)0.0759 (4)
O40.38110 (14)0.01270 (13)0.63615 (13)0.0854 (5)
O50.21156 (14)−0.09720 (10)0.66195 (11)0.0674 (4)
N10.16706 (12)0.14918 (8)0.34140 (8)0.0370 (2)
C10.07180 (15)0.13594 (11)0.14580 (10)0.0418 (3)
C60.0345 (2)0.20882 (15)0.07398 (16)0.0675 (5)
H60.08640.26860.07010.081*
C5−0.0825 (3)0.1911 (2)0.00724 (19)0.0883 (7)
H5−0.10910.2392−0.04240.106*
C4−0.1588 (2)0.1040 (2)0.01384 (19)0.0791 (6)
H4−0.23680.0930−0.03150.095*
C3−0.1220 (2)0.03292 (19)0.08598 (17)0.0730 (6)
H3−0.1757−0.02590.09040.088*
C2−0.00486 (19)0.04757 (15)0.15289 (13)0.0579 (4)
H20.0216−0.00140.20180.069*
C70.08779 (13)0.23051 (10)0.37651 (9)0.0357 (3)
C80.03879 (17)0.32027 (12)0.32950 (11)0.0460 (3)
H80.05490.33530.26400.055*
C9−0.03507 (18)0.38639 (13)0.38433 (13)0.0531 (4)
H9−0.06920.44750.35520.064*
C10−0.05955 (18)0.36374 (13)0.48191 (13)0.0540 (4)
H10−0.11010.40980.51660.065*
C11−0.01053 (15)0.27462 (12)0.52831 (11)0.0455 (3)
H11−0.02750.25990.59370.055*
C120.06533 (13)0.20672 (10)0.47474 (10)0.0357 (3)
C130.13518 (13)0.11059 (10)0.49999 (10)0.0365 (3)
C140.19335 (13)0.07571 (10)0.41739 (10)0.0363 (3)
C150.26489 (19)−0.02360 (12)0.40328 (13)0.0532 (4)
H15A0.3627−0.01170.40410.080*
H15B0.2295−0.05330.34020.080*
H15C0.2487−0.06990.45650.080*
C160.14712 (16)0.06658 (12)0.59968 (11)0.0452 (3)
C170.26169 (17)−0.00983 (13)0.63236 (11)0.0493 (3)
C180.3109 (3)−0.1732 (2)0.7043 (2)0.1025 (9)
H18A0.2623−0.23330.72320.154*
H18B0.3641−0.14490.76230.154*
H18C0.3718−0.19160.65540.154*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03642 (17)0.0496 (2)0.03534 (16)−0.00086 (13)0.01146 (12)−0.00074 (13)
O10.0557 (6)0.0625 (7)0.0528 (6)−0.0192 (5)0.0178 (5)0.0020 (5)
O20.0503 (6)0.0744 (8)0.0496 (6)0.0197 (5)0.0165 (5)−0.0029 (5)
O30.0956 (10)0.0845 (10)0.0541 (7)0.0276 (8)0.0372 (7)0.0252 (7)
O40.0485 (7)0.0996 (12)0.1047 (12)−0.0061 (7)−0.0072 (7)0.0266 (9)
O50.0687 (8)0.0525 (7)0.0791 (9)0.0015 (6)−0.0009 (7)0.0213 (6)
N10.0418 (6)0.0379 (5)0.0323 (5)0.0055 (4)0.0089 (4)0.0006 (4)
C10.0414 (7)0.0487 (7)0.0360 (6)0.0014 (6)0.0077 (5)−0.0040 (5)
C60.0771 (13)0.0509 (9)0.0697 (12)0.0030 (9)−0.0141 (10)0.0070 (8)
C50.0920 (16)0.0773 (14)0.0865 (16)0.0199 (13)−0.0320 (13)0.0062 (12)
C40.0535 (10)0.0934 (16)0.0852 (15)0.0111 (11)−0.0156 (10)−0.0224 (13)
C30.0543 (10)0.0954 (15)0.0699 (12)−0.0223 (10)0.0094 (9)−0.0153 (11)
C20.0584 (9)0.0706 (11)0.0453 (8)−0.0178 (8)0.0088 (7)0.0030 (7)
C70.0355 (6)0.0367 (6)0.0355 (6)0.0020 (5)0.0062 (5)−0.0005 (5)
C80.0529 (8)0.0445 (7)0.0411 (7)0.0079 (6)0.0073 (6)0.0063 (6)
C90.0588 (9)0.0451 (8)0.0556 (9)0.0163 (7)0.0071 (7)0.0045 (7)
C100.0546 (9)0.0527 (9)0.0565 (9)0.0165 (7)0.0137 (7)−0.0065 (7)
C110.0449 (7)0.0527 (8)0.0408 (7)0.0056 (6)0.0131 (6)−0.0030 (6)
C120.0340 (6)0.0386 (6)0.0351 (6)−0.0002 (5)0.0066 (5)0.0001 (5)
C130.0364 (6)0.0364 (6)0.0373 (6)−0.0019 (5)0.0066 (5)0.0028 (5)
C140.0359 (6)0.0347 (6)0.0385 (6)−0.0001 (5)0.0052 (5)0.0010 (5)
C150.0637 (10)0.0426 (8)0.0547 (9)0.0151 (7)0.0125 (7)0.0026 (6)
C160.0475 (7)0.0473 (7)0.0417 (7)−0.0019 (6)0.0092 (6)0.0086 (6)
C170.0504 (8)0.0546 (8)0.0419 (7)−0.0008 (7)0.0000 (6)0.0078 (6)
C180.118 (2)0.0718 (14)0.114 (2)0.0262 (14)−0.0091 (17)0.0351 (14)
Geometric parameters (Å, °) top
S1—O21.4167 (12)C7—C81.3855 (19)
S1—O11.4211 (12)C7—C121.3940 (17)
S1—N11.6800 (11)C8—C91.381 (2)
S1—C11.7498 (15)C8—H80.9300
O3—C161.2146 (19)C9—C101.388 (2)
O4—C171.190 (2)C9—H90.9300
O5—C171.313 (2)C10—C111.375 (2)
O5—C181.452 (3)C10—H100.9300
N1—C141.4001 (17)C11—C121.3968 (18)
N1—C71.4171 (16)C11—H110.9300
C1—C61.372 (2)C12—C131.4437 (18)
C1—C21.377 (2)C13—C141.3740 (18)
C6—C51.387 (3)C13—C161.4482 (19)
C6—H60.9300C14—C151.4868 (19)
C5—C41.361 (4)C15—H15A0.9600
C5—H50.9300C15—H15B0.9600
C4—C31.357 (3)C15—H15C0.9600
C4—H40.9300C16—C171.519 (2)
C3—C21.383 (3)C18—H18A0.9600
C3—H30.9300C18—H18B0.9600
C2—H20.9300C18—H18C0.9600
O2—S1—O1119.91 (8)C8—C9—H9119.2
O2—S1—N1107.26 (6)C10—C9—H9119.2
O1—S1—N1106.24 (6)C11—C10—C9121.33 (14)
O2—S1—C1109.57 (7)C11—C10—H10119.3
O1—S1—C1109.09 (7)C9—C10—H10119.3
N1—S1—C1103.46 (6)C10—C11—C12118.31 (13)
C17—O5—C18117.05 (18)C10—C11—H11120.8
C14—N1—C7109.20 (10)C12—C11—H11120.8
C14—N1—S1128.90 (9)C7—C12—C11119.45 (12)
C7—N1—S1121.80 (9)C7—C12—C13107.25 (11)
C6—C1—C2121.38 (16)C11—C12—C13133.27 (12)
C6—C1—S1119.78 (13)C14—C13—C12108.61 (11)
C2—C1—S1118.79 (12)C14—C13—C16128.05 (13)
C1—C6—C5118.3 (2)C12—C13—C16123.18 (12)
C1—C6—H6120.8C13—C14—N1107.73 (11)
C5—C6—H6120.8C13—C14—C15128.83 (12)
C4—C5—C6120.6 (2)N1—C14—C15123.34 (12)
C4—C5—H5119.7C14—C15—H15A109.5
C6—C5—H5119.7C14—C15—H15B109.5
C3—C4—C5120.62 (19)H15A—C15—H15B109.5
C3—C4—H4119.7C14—C15—H15C109.5
C5—C4—H4119.7H15A—C15—H15C109.5
C4—C3—C2120.3 (2)H15B—C15—H15C109.5
C4—C3—H3119.9O3—C16—C13122.78 (14)
C2—C3—H3119.9O3—C16—C17116.24 (14)
C1—C2—C3118.81 (18)C13—C16—C17120.53 (13)
C1—C2—H2120.6O4—C17—O5126.15 (16)
C3—C2—H2120.6O4—C17—C16121.99 (16)
C8—C7—C12122.44 (12)O5—C17—C16111.65 (14)
C8—C7—N1130.39 (12)O5—C18—H18A109.5
C12—C7—N1107.16 (11)O5—C18—H18B109.5
C9—C8—C7116.94 (14)H18A—C18—H18B109.5
C9—C8—H8121.5O5—C18—H18C109.5
C7—C8—H8121.5H18A—C18—H18C109.5
C8—C9—C10121.51 (14)H18B—C18—H18C109.5
O2—S1—N1—C14−2.26 (14)C8—C7—C12—C110.7 (2)
O1—S1—N1—C14−131.63 (12)N1—C7—C12—C11179.80 (12)
C1—S1—N1—C14113.53 (13)C8—C7—C12—C13−177.69 (13)
O2—S1—N1—C7173.58 (11)N1—C7—C12—C131.38 (14)
O1—S1—N1—C744.21 (12)C10—C11—C12—C7−0.6 (2)
C1—S1—N1—C7−70.63 (12)C10—C11—C12—C13177.32 (15)
O2—S1—C1—C6−123.37 (15)C7—C12—C13—C14−2.33 (15)
O1—S1—C1—C69.72 (16)C11—C12—C13—C14179.56 (15)
N1—S1—C1—C6122.50 (15)C7—C12—C13—C16173.39 (13)
O2—S1—C1—C254.13 (14)C11—C12—C13—C16−4.7 (2)
O1—S1—C1—C2−172.79 (12)C12—C13—C14—N12.31 (15)
N1—S1—C1—C2−60.00 (13)C16—C13—C14—N1−173.13 (13)
C2—C1—C6—C5−0.6 (3)C12—C13—C14—C15−174.14 (14)
S1—C1—C6—C5176.80 (18)C16—C13—C14—C1510.4 (2)
C1—C6—C5—C40.6 (4)C7—N1—C14—C13−1.47 (15)
C6—C5—C4—C30.2 (4)S1—N1—C14—C13174.79 (10)
C5—C4—C3—C2−1.0 (4)C7—N1—C14—C15175.23 (13)
C6—C1—C2—C3−0.2 (3)S1—N1—C14—C15−8.5 (2)
S1—C1—C2—C3−177.64 (14)C14—C13—C16—O3−170.51 (16)
C4—C3—C2—C11.0 (3)C12—C13—C16—O314.6 (2)
C14—N1—C7—C8178.98 (15)C14—C13—C16—C1717.5 (2)
S1—N1—C7—C82.4 (2)C12—C13—C16—C17−157.34 (14)
C14—N1—C7—C120.00 (15)C18—O5—C17—O40.7 (3)
S1—N1—C7—C12−176.57 (9)C18—O5—C17—C16−174.17 (19)
C12—C7—C8—C9−0.3 (2)O3—C16—C17—O4−110.8 (2)
N1—C7—C8—C9−179.13 (15)C13—C16—C17—O461.7 (2)
C7—C8—C9—C10−0.3 (3)O3—C16—C17—O564.3 (2)
C8—C9—C10—C110.4 (3)C13—C16—C17—O5−123.17 (16)
C9—C10—C11—C120.1 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.932.463.219 (2)139
C15—H15A···O4ii0.962.603.533 (2)164
C6—H6···O10.932.542.908 (2)104
C8—H8···O10.932.543.024 (2)113
C11—H11···O30.932.513.021 (2)115
C15—H15B···O20.962.422.793 (2)103
C4—H4···Cg3iii0.932.803.495 (2)132
C5—H5···Cg1iii0.932.883.526 (3)128
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1/2, −y+1/2, z−1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O3i0.932.463.219 (2)139
C15—H15A···O4ii0.962.603.533 (2)164
C6—H6···O10.932.542.908 (2)104
C8—H8···O10.932.543.024 (2)113
C11—H11···O30.932.513.021 (2)115
C15—H15B···O20.962.422.793 (2)103
C4—H4···Cg3iii0.932.803.495 (2)132
C5—H5···Cg1iii0.932.883.526 (3)128
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1; (iii) x−1/2, −y+1/2, z−1/2.
Acknowledgements top

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

references
References top

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