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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...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036987/is2199sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036987/is2199Isup2.hkl
Contains datablock I

CCDC reference: 660185

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.132
  • Data-to-parameter ratio = 24.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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).

Structure description 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.

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).

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
C18H15NO5SF(000) = 744
Mr = 357.37Dx = 1.411 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8031 reflections
a = 9.7005 (3) Åθ = 2.2–31.5°
b = 12.9924 (4) ŵ = 0.22 mm1
c = 13.4224 (3) ÅT = 295 K
β = 96.189 (1)°Block, 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)
Graphite monochromatorRint = 0.024
ω and φ scansθmax = 31.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.882, Tmax = 0.966k = 1918
23482 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0649P)2 + 0.3886P]
where P = (Fo2 + 2Fc2)/3
5550 reflections(Δ/σ)max < 0.001
227 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C18H15NO5SV = 1681.80 (8) Å3
Mr = 357.37Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.7005 (3) ŵ = 0.22 mm1
b = 12.9924 (4) ÅT = 295 K
c = 13.4224 (3) Å0.20 × 0.16 × 0.16 mm
β = 96.189 (1)°
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)] = 0.0430 restraints
wR(F2) = 0.132H-atom parameters constrained
S = 1.04Δρmax = 0.33 e Å3
5550 reflectionsΔρmin = 0.33 e Å3
227 parameters
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*
C50.0825 (3)0.1911 (2)0.00724 (19)0.0883 (7)
H50.10910.23920.04240.106*
C40.1588 (2)0.1040 (2)0.01384 (19)0.0791 (6)
H40.23680.09300.03150.095*
C30.1220 (2)0.03292 (19)0.08598 (17)0.0730 (6)
H30.17570.02590.09040.088*
C20.00486 (19)0.04757 (15)0.15289 (13)0.0579 (4)
H20.02160.00140.20180.069*
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*
C90.03507 (18)0.38639 (13)0.38433 (13)0.0531 (4)
H90.06920.44750.35520.064*
C100.05955 (18)0.36374 (13)0.48191 (13)0.0540 (4)
H100.11010.40980.51660.065*
C110.01053 (15)0.27462 (12)0.52831 (11)0.0455 (3)
H110.02750.25990.59370.055*
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)
H15A0.36270.01170.40410.080*
H15B0.22950.05330.34020.080*
H15C0.24870.06990.45650.080*
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)
H18A0.26230.23330.72320.154*
H18B0.36410.14490.76230.154*
H18C0.37180.19160.65540.154*
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, º) 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—C142.26 (14)C8—C7—C12—C110.7 (2)
O1—S1—N1—C14131.63 (12)N1—C7—C12—C11179.80 (12)
C1—S1—N1—C14113.53 (13)C8—C7—C12—C13177.69 (13)
O2—S1—N1—C7173.58 (11)N1—C7—C12—C131.38 (14)
O1—S1—N1—C744.21 (12)C10—C11—C12—C70.6 (2)
C1—S1—N1—C770.63 (12)C10—C11—C12—C13177.32 (15)
O2—S1—C1—C6123.37 (15)C7—C12—C13—C142.33 (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—C164.7 (2)
O1—S1—C1—C2172.79 (12)C12—C13—C14—N12.31 (15)
N1—S1—C1—C260.00 (13)C16—C13—C14—N1173.13 (13)
C2—C1—C6—C50.6 (3)C12—C13—C14—C15174.14 (14)
S1—C1—C6—C5176.80 (18)C16—C13—C14—C1510.4 (2)
C1—C6—C5—C40.6 (4)C7—N1—C14—C131.47 (15)
C6—C5—C4—C30.2 (4)S1—N1—C14—C13174.79 (10)
C5—C4—C3—C21.0 (4)C7—N1—C14—C15175.23 (13)
C6—C1—C2—C30.2 (3)S1—N1—C14—C158.5 (2)
S1—C1—C2—C3177.64 (14)C14—C13—C16—O3170.51 (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—C17157.34 (14)
C14—N1—C7—C120.00 (15)C18—O5—C17—O40.7 (3)
S1—N1—C7—C12176.57 (9)C18—O5—C17—C16174.17 (19)
C12—C7—C8—C90.3 (2)O3—C16—C17—O4110.8 (2)
N1—C7—C8—C9179.13 (15)C13—C16—C17—O461.7 (2)
C7—C8—C9—C100.3 (3)O3—C16—C17—O564.3 (2)
C8—C9—C10—C110.4 (3)C13—C16—C17—O5123.17 (16)
C9—C10—C11—C120.1 (3)
Hydrogen-bond geometry (Å, º) 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) x1/2, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC18H15NO5S
Mr357.37
Crystal system, space groupMonoclinic, P21/n
Temperature (K)295
a, b, c (Å)9.7005 (3), 12.9924 (4), 13.4224 (3)
β (°) 96.189 (1)
V3)1681.80 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.20 × 0.16 × 0.16
Data collection
DiffractometerBruker Kappa APEX II
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.882, 0.966
No. of measured, independent and
observed [I > 2σ(I)] reflections
23482, 5550, 4082
Rint0.024
(sin θ/λ)max1)0.734
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.132, 1.04
No. of reflections5550
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.33

Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) 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) x1/2, y+1/2, z1/2.
 

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