Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036987/is2199sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036987/is2199Isup2.hkl |
CCDC reference: 660185
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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.
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).
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).
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.
C18H15NO5S | F(000) = 744 |
Mr = 357.37 | Dx = 1.411 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8031 reflections |
a = 9.7005 (3) Å | θ = 2.2–31.5° |
b = 12.9924 (4) Å | µ = 0.22 mm−1 |
c = 13.4224 (3) Å | T = 295 K |
β = 96.189 (1)° | Block, colourless |
V = 1681.80 (8) Å3 | 0.20 × 0.16 × 0.16 mm |
Z = 4 |
Bruker Kappa APEX II diffractometer | 5550 independent reflections |
Radiation source: fine-focus sealed tube | 4082 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω and φ scans | θmax = 31.5°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.882, Tmax = 0.966 | k = −19→18 |
23482 measured reflections | l = −19→19 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H-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 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C18H15NO5S | V = 1681.80 (8) Å3 |
Mr = 357.37 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.7005 (3) Å | µ = 0.22 mm−1 |
b = 12.9924 (4) Å | T = 295 K |
c = 13.4224 (3) Å | 0.20 × 0.16 × 0.16 mm |
β = 96.189 (1)° |
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 = 0.966 | Rint = 0.024 |
23482 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.33 e Å−3 |
5550 reflections | Δρmin = −0.33 e Å−3 |
227 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.22348 (3) | 0.15223 (3) | 0.22741 (2) | 0.03990 (10) | |
O1 | 0.27574 (12) | 0.25315 (10) | 0.21547 (9) | 0.0561 (3) | |
O2 | 0.31128 (12) | 0.06594 (11) | 0.22066 (8) | 0.0573 (3) | |
O3 | 0.07775 (17) | 0.09577 (12) | 0.66431 (10) | 0.0759 (4) | |
O4 | 0.38110 (14) | 0.01270 (13) | 0.63615 (13) | 0.0854 (5) | |
O5 | 0.21156 (14) | −0.09720 (10) | 0.66195 (11) | 0.0674 (4) | |
N1 | 0.16706 (12) | 0.14918 (8) | 0.34140 (8) | 0.0370 (2) | |
C1 | 0.07180 (15) | 0.13594 (11) | 0.14580 (10) | 0.0418 (3) | |
C6 | 0.0345 (2) | 0.20882 (15) | 0.07398 (16) | 0.0675 (5) | |
H6 | 0.0864 | 0.2686 | 0.0701 | 0.081* | |
C5 | −0.0825 (3) | 0.1911 (2) | 0.00724 (19) | 0.0883 (7) | |
H5 | −0.1091 | 0.2392 | −0.0424 | 0.106* | |
C4 | −0.1588 (2) | 0.1040 (2) | 0.01384 (19) | 0.0791 (6) | |
H4 | −0.2368 | 0.0930 | −0.0315 | 0.095* | |
C3 | −0.1220 (2) | 0.03292 (19) | 0.08598 (17) | 0.0730 (6) | |
H3 | −0.1757 | −0.0259 | 0.0904 | 0.088* | |
C2 | −0.00486 (19) | 0.04757 (15) | 0.15289 (13) | 0.0579 (4) | |
H2 | 0.0216 | −0.0014 | 0.2018 | 0.069* | |
C7 | 0.08779 (13) | 0.23051 (10) | 0.37651 (9) | 0.0357 (3) | |
C8 | 0.03879 (17) | 0.32027 (12) | 0.32950 (11) | 0.0460 (3) | |
H8 | 0.0549 | 0.3353 | 0.2640 | 0.055* | |
C9 | −0.03507 (18) | 0.38639 (13) | 0.38433 (13) | 0.0531 (4) | |
H9 | −0.0692 | 0.4475 | 0.3552 | 0.064* | |
C10 | −0.05955 (18) | 0.36374 (13) | 0.48191 (13) | 0.0540 (4) | |
H10 | −0.1101 | 0.4098 | 0.5166 | 0.065* | |
C11 | −0.01053 (15) | 0.27462 (12) | 0.52831 (11) | 0.0455 (3) | |
H11 | −0.0275 | 0.2599 | 0.5937 | 0.055* | |
C12 | 0.06533 (13) | 0.20672 (10) | 0.47474 (10) | 0.0357 (3) | |
C13 | 0.13518 (13) | 0.11059 (10) | 0.49999 (10) | 0.0365 (3) | |
C14 | 0.19335 (13) | 0.07571 (10) | 0.41739 (10) | 0.0363 (3) | |
C15 | 0.26489 (19) | −0.02360 (12) | 0.40328 (13) | 0.0532 (4) | |
H15A | 0.3627 | −0.0117 | 0.4041 | 0.080* | |
H15B | 0.2295 | −0.0533 | 0.3402 | 0.080* | |
H15C | 0.2487 | −0.0699 | 0.4565 | 0.080* | |
C16 | 0.14712 (16) | 0.06658 (12) | 0.59968 (11) | 0.0452 (3) | |
C17 | 0.26169 (17) | −0.00983 (13) | 0.63236 (11) | 0.0493 (3) | |
C18 | 0.3109 (3) | −0.1732 (2) | 0.7043 (2) | 0.1025 (9) | |
H18A | 0.2623 | −0.2333 | 0.7232 | 0.154* | |
H18B | 0.3641 | −0.1449 | 0.7623 | 0.154* | |
H18C | 0.3718 | −0.1916 | 0.6554 | 0.154* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03642 (17) | 0.0496 (2) | 0.03534 (16) | −0.00086 (13) | 0.01146 (12) | −0.00074 (13) |
O1 | 0.0557 (6) | 0.0625 (7) | 0.0528 (6) | −0.0192 (5) | 0.0178 (5) | 0.0020 (5) |
O2 | 0.0503 (6) | 0.0744 (8) | 0.0496 (6) | 0.0197 (5) | 0.0165 (5) | −0.0029 (5) |
O3 | 0.0956 (10) | 0.0845 (10) | 0.0541 (7) | 0.0276 (8) | 0.0372 (7) | 0.0252 (7) |
O4 | 0.0485 (7) | 0.0996 (12) | 0.1047 (12) | −0.0061 (7) | −0.0072 (7) | 0.0266 (9) |
O5 | 0.0687 (8) | 0.0525 (7) | 0.0791 (9) | 0.0015 (6) | −0.0009 (7) | 0.0213 (6) |
N1 | 0.0418 (6) | 0.0379 (5) | 0.0323 (5) | 0.0055 (4) | 0.0089 (4) | 0.0006 (4) |
C1 | 0.0414 (7) | 0.0487 (7) | 0.0360 (6) | 0.0014 (6) | 0.0077 (5) | −0.0040 (5) |
C6 | 0.0771 (13) | 0.0509 (9) | 0.0697 (12) | 0.0030 (9) | −0.0141 (10) | 0.0070 (8) |
C5 | 0.0920 (16) | 0.0773 (14) | 0.0865 (16) | 0.0199 (13) | −0.0320 (13) | 0.0062 (12) |
C4 | 0.0535 (10) | 0.0934 (16) | 0.0852 (15) | 0.0111 (11) | −0.0156 (10) | −0.0224 (13) |
C3 | 0.0543 (10) | 0.0954 (15) | 0.0699 (12) | −0.0223 (10) | 0.0094 (9) | −0.0153 (11) |
C2 | 0.0584 (9) | 0.0706 (11) | 0.0453 (8) | −0.0178 (8) | 0.0088 (7) | 0.0030 (7) |
C7 | 0.0355 (6) | 0.0367 (6) | 0.0355 (6) | 0.0020 (5) | 0.0062 (5) | −0.0005 (5) |
C8 | 0.0529 (8) | 0.0445 (7) | 0.0411 (7) | 0.0079 (6) | 0.0073 (6) | 0.0063 (6) |
C9 | 0.0588 (9) | 0.0451 (8) | 0.0556 (9) | 0.0163 (7) | 0.0071 (7) | 0.0045 (7) |
C10 | 0.0546 (9) | 0.0527 (9) | 0.0565 (9) | 0.0165 (7) | 0.0137 (7) | −0.0065 (7) |
C11 | 0.0449 (7) | 0.0527 (8) | 0.0408 (7) | 0.0056 (6) | 0.0131 (6) | −0.0030 (6) |
C12 | 0.0340 (6) | 0.0386 (6) | 0.0351 (6) | −0.0002 (5) | 0.0066 (5) | 0.0001 (5) |
C13 | 0.0364 (6) | 0.0364 (6) | 0.0373 (6) | −0.0019 (5) | 0.0066 (5) | 0.0028 (5) |
C14 | 0.0359 (6) | 0.0347 (6) | 0.0385 (6) | −0.0001 (5) | 0.0052 (5) | 0.0010 (5) |
C15 | 0.0637 (10) | 0.0426 (8) | 0.0547 (9) | 0.0151 (7) | 0.0125 (7) | 0.0026 (6) |
C16 | 0.0475 (7) | 0.0473 (7) | 0.0417 (7) | −0.0019 (6) | 0.0092 (6) | 0.0086 (6) |
C17 | 0.0504 (8) | 0.0546 (8) | 0.0419 (7) | −0.0008 (7) | 0.0000 (6) | 0.0078 (6) |
C18 | 0.118 (2) | 0.0718 (14) | 0.114 (2) | 0.0262 (14) | −0.0091 (17) | 0.0351 (14) |
S1—O2 | 1.4167 (12) | C7—C8 | 1.3855 (19) |
S1—O1 | 1.4211 (12) | C7—C12 | 1.3940 (17) |
S1—N1 | 1.6800 (11) | C8—C9 | 1.381 (2) |
S1—C1 | 1.7498 (15) | C8—H8 | 0.9300 |
O3—C16 | 1.2146 (19) | C9—C10 | 1.388 (2) |
O4—C17 | 1.190 (2) | C9—H9 | 0.9300 |
O5—C17 | 1.313 (2) | C10—C11 | 1.375 (2) |
O5—C18 | 1.452 (3) | C10—H10 | 0.9300 |
N1—C14 | 1.4001 (17) | C11—C12 | 1.3968 (18) |
N1—C7 | 1.4171 (16) | C11—H11 | 0.9300 |
C1—C6 | 1.372 (2) | C12—C13 | 1.4437 (18) |
C1—C2 | 1.377 (2) | C13—C14 | 1.3740 (18) |
C6—C5 | 1.387 (3) | C13—C16 | 1.4482 (19) |
C6—H6 | 0.9300 | C14—C15 | 1.4868 (19) |
C5—C4 | 1.361 (4) | C15—H15A | 0.9600 |
C5—H5 | 0.9300 | C15—H15B | 0.9600 |
C4—C3 | 1.357 (3) | C15—H15C | 0.9600 |
C4—H4 | 0.9300 | C16—C17 | 1.519 (2) |
C3—C2 | 1.383 (3) | C18—H18A | 0.9600 |
C3—H3 | 0.9300 | C18—H18B | 0.9600 |
C2—H2 | 0.9300 | C18—H18C | 0.9600 |
O2—S1—O1 | 119.91 (8) | C8—C9—H9 | 119.2 |
O2—S1—N1 | 107.26 (6) | C10—C9—H9 | 119.2 |
O1—S1—N1 | 106.24 (6) | C11—C10—C9 | 121.33 (14) |
O2—S1—C1 | 109.57 (7) | C11—C10—H10 | 119.3 |
O1—S1—C1 | 109.09 (7) | C9—C10—H10 | 119.3 |
N1—S1—C1 | 103.46 (6) | C10—C11—C12 | 118.31 (13) |
C17—O5—C18 | 117.05 (18) | C10—C11—H11 | 120.8 |
C14—N1—C7 | 109.20 (10) | C12—C11—H11 | 120.8 |
C14—N1—S1 | 128.90 (9) | C7—C12—C11 | 119.45 (12) |
C7—N1—S1 | 121.80 (9) | C7—C12—C13 | 107.25 (11) |
C6—C1—C2 | 121.38 (16) | C11—C12—C13 | 133.27 (12) |
C6—C1—S1 | 119.78 (13) | C14—C13—C12 | 108.61 (11) |
C2—C1—S1 | 118.79 (12) | C14—C13—C16 | 128.05 (13) |
C1—C6—C5 | 118.3 (2) | C12—C13—C16 | 123.18 (12) |
C1—C6—H6 | 120.8 | C13—C14—N1 | 107.73 (11) |
C5—C6—H6 | 120.8 | C13—C14—C15 | 128.83 (12) |
C4—C5—C6 | 120.6 (2) | N1—C14—C15 | 123.34 (12) |
C4—C5—H5 | 119.7 | C14—C15—H15A | 109.5 |
C6—C5—H5 | 119.7 | C14—C15—H15B | 109.5 |
C3—C4—C5 | 120.62 (19) | H15A—C15—H15B | 109.5 |
C3—C4—H4 | 119.7 | C14—C15—H15C | 109.5 |
C5—C4—H4 | 119.7 | H15A—C15—H15C | 109.5 |
C4—C3—C2 | 120.3 (2) | H15B—C15—H15C | 109.5 |
C4—C3—H3 | 119.9 | O3—C16—C13 | 122.78 (14) |
C2—C3—H3 | 119.9 | O3—C16—C17 | 116.24 (14) |
C1—C2—C3 | 118.81 (18) | C13—C16—C17 | 120.53 (13) |
C1—C2—H2 | 120.6 | O4—C17—O5 | 126.15 (16) |
C3—C2—H2 | 120.6 | O4—C17—C16 | 121.99 (16) |
C8—C7—C12 | 122.44 (12) | O5—C17—C16 | 111.65 (14) |
C8—C7—N1 | 130.39 (12) | O5—C18—H18A | 109.5 |
C12—C7—N1 | 107.16 (11) | O5—C18—H18B | 109.5 |
C9—C8—C7 | 116.94 (14) | H18A—C18—H18B | 109.5 |
C9—C8—H8 | 121.5 | O5—C18—H18C | 109.5 |
C7—C8—H8 | 121.5 | H18A—C18—H18C | 109.5 |
C8—C9—C10 | 121.51 (14) | H18B—C18—H18C | 109.5 |
O2—S1—N1—C14 | −2.26 (14) | C8—C7—C12—C11 | 0.7 (2) |
O1—S1—N1—C14 | −131.63 (12) | N1—C7—C12—C11 | 179.80 (12) |
C1—S1—N1—C14 | 113.53 (13) | C8—C7—C12—C13 | −177.69 (13) |
O2—S1—N1—C7 | 173.58 (11) | N1—C7—C12—C13 | 1.38 (14) |
O1—S1—N1—C7 | 44.21 (12) | C10—C11—C12—C7 | −0.6 (2) |
C1—S1—N1—C7 | −70.63 (12) | C10—C11—C12—C13 | 177.32 (15) |
O2—S1—C1—C6 | −123.37 (15) | C7—C12—C13—C14 | −2.33 (15) |
O1—S1—C1—C6 | 9.72 (16) | C11—C12—C13—C14 | 179.56 (15) |
N1—S1—C1—C6 | 122.50 (15) | C7—C12—C13—C16 | 173.39 (13) |
O2—S1—C1—C2 | 54.13 (14) | C11—C12—C13—C16 | −4.7 (2) |
O1—S1—C1—C2 | −172.79 (12) | C12—C13—C14—N1 | 2.31 (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—C5 | 176.80 (18) | C16—C13—C14—C15 | 10.4 (2) |
C1—C6—C5—C4 | 0.6 (4) | C7—N1—C14—C13 | −1.47 (15) |
C6—C5—C4—C3 | 0.2 (4) | S1—N1—C14—C13 | 174.79 (10) |
C5—C4—C3—C2 | −1.0 (4) | C7—N1—C14—C15 | 175.23 (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—C1 | 1.0 (3) | C12—C13—C16—O3 | 14.6 (2) |
C14—N1—C7—C8 | 178.98 (15) | C14—C13—C16—C17 | 17.5 (2) |
S1—N1—C7—C8 | 2.4 (2) | C12—C13—C16—C17 | −157.34 (14) |
C14—N1—C7—C12 | 0.00 (15) | C18—O5—C17—O4 | 0.7 (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—O4 | 61.7 (2) |
C7—C8—C9—C10 | −0.3 (3) | O3—C16—C17—O5 | 64.3 (2) |
C8—C9—C10—C11 | 0.4 (3) | C13—C16—C17—O5 | −123.17 (16) |
C9—C10—C11—C12 | 0.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3i | 0.93 | 2.46 | 3.219 (2) | 139 |
C15—H15A···O4ii | 0.96 | 2.60 | 3.533 (2) | 164 |
C6—H6···O1 | 0.93 | 2.54 | 2.908 (2) | 104 |
C8—H8···O1 | 0.93 | 2.54 | 3.024 (2) | 113 |
C11—H11···O3 | 0.93 | 2.51 | 3.021 (2) | 115 |
C15—H15B···O2 | 0.96 | 2.42 | 2.793 (2) | 103 |
C4—H4···Cg3iii | 0.93 | 2.80 | 3.495 (2) | 132 |
C5—H5···Cg1iii | 0.93 | 2.88 | 3.526 (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. |
Experimental details
Crystal data | |
Chemical formula | C18H15NO5S |
Mr | 357.37 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 9.7005 (3), 12.9924 (4), 13.4224 (3) |
β (°) | 96.189 (1) |
V (Å3) | 1681.80 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.20 × 0.16 × 0.16 |
Data collection | |
Diffractometer | Bruker Kappa APEX II |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.882, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23482, 5550, 4082 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.734 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.132, 1.04 |
No. of reflections | 5550 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.33, −0.33 |
Computer programs: APEX2 (Bruker, 2004), APEX2, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O3i | 0.93 | 2.46 | 3.219 (2) | 139 |
C15—H15A···O4ii | 0.96 | 2.60 | 3.533 (2) | 164 |
C6—H6···O1 | 0.93 | 2.54 | 2.908 (2) | 104 |
C8—H8···O1 | 0.93 | 2.54 | 3.024 (2) | 113 |
C11—H11···O3 | 0.93 | 2.51 | 3.021 (2) | 115 |
C15—H15B···O2 | 0.96 | 2.42 | 2.793 (2) | 103 |
C4—H4···Cg3iii | 0.93 | 2.80 | 3.495 (2) | 132 |
C5—H5···Cg1iii | 0.93 | 2.88 | 3.526 (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. |
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.