Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039899/ci6720sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039899/ci6720Isup2.hkl |
CCDC reference: 296541
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.052
- wR factor = 0.145
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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
A solution of 2-methyl-3-methylindole (4 mmol) in dry tetrahydrofuran (THF, 10 ml) was added slowly to a stirred suspension of 50% sodium hydride (0.24 g, 10 mmol) in dry THF (4 ml) under nitrogen atmosphere at room temperature. The reaction mixture was refluxed for 3 h and cooled to 268 K. A solution of phenylsulfonyl chloride (0.86 ml, 6 mmol) in dry THF (8.0 ml) was then added slowly. The reaction mixture was stirred at 268 K for 6 h. The solution was then treated with saturated ammonium chloride solution (20 ml) and the organic layer was separated. The aqueous layer was extracted with chloroform (4 × 15 ml), and the combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give a white oil. It was crystallized from ethyl acetate and hexane (2:8) to give a white crystalline colourless solid (yield 81%, m.p. 413 K). IR (KBr): 1380, 1140 cm−1.
H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H = 0.93 or 0.96 Å and Uiso(H) = 1.2–1.5Ueq(C).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C16H15NO2S | Z = 2 |
Mr = 285.35 | F(000) = 300 |
Triclinic, P1 | Dx = 1.346 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8800 (13) Å | Cell parameters from 2540 reflections |
b = 9.6020 (16) Å | θ = 2.1–28.0° |
c = 9.9864 (17) Å | µ = 0.23 mm−1 |
α = 82.210 (3)° | T = 293 K |
β = 81.487 (3)° | Block, yellow |
γ = 71.087 (3)° | 0.23 × 0.21 × 0.19 mm |
V = 703.8 (2) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 3284 independent reflections |
Radiation source: fine-focus sealed tube | 2540 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 28.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.948, Tmax = 0.957 | k = −12→12 |
8276 measured reflections | l = −13→13 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0803P)2 + 0.1221P] where P = (Fo2 + 2Fc2)/3 |
3284 reflections | (Δ/σ)max = 0.001 |
183 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C16H15NO2S | γ = 71.087 (3)° |
Mr = 285.35 | V = 703.8 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8800 (13) Å | Mo Kα radiation |
b = 9.6020 (16) Å | µ = 0.23 mm−1 |
c = 9.9864 (17) Å | T = 293 K |
α = 82.210 (3)° | 0.23 × 0.21 × 0.19 mm |
β = 81.487 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 3284 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2540 reflections with I > 2σ(I) |
Tmin = 0.948, Tmax = 0.957 | Rint = 0.017 |
8276 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.31 e Å−3 |
3284 reflections | Δρmin = −0.19 e Å−3 |
183 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 | ||
S1 | 0.64895 (7) | 0.26735 (6) | 0.29715 (5) | 0.04878 (19) | |
O1 | 0.5211 (2) | 0.3495 (2) | 0.39625 (15) | 0.0666 (4) | |
O2 | 0.6228 (2) | 0.14126 (18) | 0.25539 (18) | 0.0693 (5) | |
N1 | 0.6570 (2) | 0.38450 (16) | 0.16001 (15) | 0.0423 (4) | |
C2 | 0.7372 (3) | 0.3440 (2) | 0.02641 (19) | 0.0466 (4) | |
C3 | 0.7743 (3) | 0.4608 (2) | −0.0462 (2) | 0.0522 (5) | |
C4 | 0.7265 (3) | 0.5795 (2) | 0.0400 (2) | 0.0519 (5) | |
C5 | 0.6564 (2) | 0.5308 (2) | 0.1672 (2) | 0.0445 (4) | |
C6 | 0.5997 (3) | 0.6209 (2) | 0.2737 (2) | 0.0592 (6) | |
H6 | 0.5524 | 0.5881 | 0.3585 | 0.071* | |
C7 | 0.6165 (4) | 0.7602 (3) | 0.2483 (4) | 0.0809 (9) | |
H7 | 0.5813 | 0.8221 | 0.3181 | 0.097* | |
C8 | 0.6837 (4) | 0.8110 (3) | 0.1230 (4) | 0.0924 (10) | |
H8 | 0.6915 | 0.9065 | 0.1096 | 0.111* | |
C9 | 0.7390 (4) | 0.7233 (3) | 0.0180 (3) | 0.0797 (8) | |
H9 | 0.7843 | 0.7584 | −0.0665 | 0.096* | |
C10 | 0.8644 (3) | 0.2158 (2) | 0.3528 (2) | 0.0507 (5) | |
C11 | 0.8989 (3) | 0.2984 (3) | 0.4425 (2) | 0.0650 (6) | |
H11 | 0.8089 | 0.3798 | 0.4757 | 0.078* | |
C12 | 1.0709 (4) | 0.2564 (4) | 0.4814 (3) | 0.0819 (8) | |
H12 | 1.0967 | 0.3103 | 0.5421 | 0.098* | |
C13 | 1.2032 (4) | 0.1377 (4) | 0.4327 (3) | 0.0894 (10) | |
H13 | 1.3188 | 0.1123 | 0.4587 | 0.107* | |
C14 | 1.1660 (4) | 0.0558 (4) | 0.3453 (3) | 0.0920 (10) | |
H14 | 1.2561 | −0.0261 | 0.3132 | 0.110* | |
C15 | 0.9958 (3) | 0.0943 (3) | 0.3047 (3) | 0.0726 (7) | |
H15 | 0.9702 | 0.0386 | 0.2456 | 0.087* | |
C16 | 0.7607 (4) | 0.1980 (3) | −0.0208 (3) | 0.0699 (7) | |
H16A | 0.8007 | 0.1997 | −0.1164 | 0.105* | |
H16B | 0.6476 | 0.1774 | −0.0043 | 0.105* | |
H16C | 0.8488 | 0.1225 | 0.0278 | 0.105* | |
C17 | 0.8497 (4) | 0.4709 (4) | −0.1925 (2) | 0.0827 (8) | |
H17A | 0.8684 | 0.3790 | −0.2293 | 0.124* | |
H17B | 0.9627 | 0.4907 | −0.1997 | 0.124* | |
H17C | 0.7664 | 0.5493 | −0.2425 | 0.124* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0484 (3) | 0.0565 (3) | 0.0449 (3) | −0.0246 (2) | −0.0030 (2) | 0.0018 (2) |
O1 | 0.0532 (9) | 0.0957 (12) | 0.0495 (8) | −0.0267 (8) | 0.0076 (7) | −0.0071 (8) |
O2 | 0.0780 (11) | 0.0621 (10) | 0.0818 (11) | −0.0429 (8) | −0.0145 (9) | 0.0038 (8) |
N1 | 0.0478 (8) | 0.0411 (8) | 0.0381 (8) | −0.0139 (7) | −0.0035 (6) | −0.0054 (6) |
C2 | 0.0427 (10) | 0.0533 (11) | 0.0411 (10) | −0.0085 (8) | −0.0058 (8) | −0.0103 (8) |
C3 | 0.0421 (10) | 0.0690 (13) | 0.0425 (10) | −0.0157 (9) | −0.0048 (8) | 0.0014 (9) |
C4 | 0.0448 (10) | 0.0527 (11) | 0.0593 (12) | −0.0180 (9) | −0.0123 (9) | 0.0057 (9) |
C5 | 0.0398 (9) | 0.0420 (10) | 0.0523 (11) | −0.0108 (8) | −0.0104 (8) | −0.0051 (8) |
C6 | 0.0562 (12) | 0.0529 (12) | 0.0675 (14) | −0.0052 (10) | −0.0175 (10) | −0.0202 (10) |
C7 | 0.0755 (17) | 0.0538 (14) | 0.117 (2) | −0.0026 (12) | −0.0394 (17) | −0.0326 (16) |
C8 | 0.098 (2) | 0.0469 (14) | 0.146 (3) | −0.0280 (14) | −0.050 (2) | −0.0009 (17) |
C9 | 0.0770 (17) | 0.0654 (16) | 0.103 (2) | −0.0361 (13) | −0.0269 (15) | 0.0228 (15) |
C10 | 0.0496 (11) | 0.0592 (12) | 0.0429 (10) | −0.0220 (9) | −0.0049 (8) | 0.0091 (9) |
C11 | 0.0687 (14) | 0.0699 (15) | 0.0617 (14) | −0.0288 (12) | −0.0182 (11) | 0.0062 (11) |
C12 | 0.0818 (18) | 0.100 (2) | 0.0783 (18) | −0.0450 (17) | −0.0346 (15) | 0.0151 (15) |
C13 | 0.0552 (15) | 0.135 (3) | 0.0742 (18) | −0.0334 (17) | −0.0195 (14) | 0.0274 (18) |
C14 | 0.0607 (16) | 0.116 (2) | 0.0743 (18) | 0.0030 (15) | −0.0081 (14) | 0.0019 (17) |
C15 | 0.0664 (15) | 0.0834 (17) | 0.0585 (14) | −0.0105 (13) | −0.0098 (11) | −0.0034 (13) |
C16 | 0.0851 (17) | 0.0620 (14) | 0.0601 (14) | −0.0097 (12) | −0.0133 (12) | −0.0239 (11) |
C17 | 0.0644 (15) | 0.124 (2) | 0.0481 (13) | −0.0241 (15) | 0.0029 (11) | 0.0073 (14) |
S1—O2 | 1.4166 (16) | C9—H9 | 0.93 |
S1—O1 | 1.4203 (16) | C10—C15 | 1.373 (3) |
S1—N1 | 1.6577 (16) | C10—C11 | 1.382 (3) |
S1—C10 | 1.760 (2) | C11—C12 | 1.382 (4) |
N1—C5 | 1.415 (2) | C11—H11 | 0.93 |
N1—C2 | 1.436 (2) | C12—C13 | 1.361 (4) |
C2—C3 | 1.341 (3) | C12—H12 | 0.93 |
C2—C16 | 1.486 (3) | C13—C14 | 1.370 (4) |
C3—C4 | 1.440 (3) | C13—H13 | 0.93 |
C3—C17 | 1.497 (3) | C14—C15 | 1.378 (4) |
C4—C5 | 1.392 (3) | C14—H14 | 0.93 |
C4—C9 | 1.401 (3) | C15—H15 | 0.93 |
C5—C6 | 1.391 (3) | C16—H16A | 0.96 |
C6—C7 | 1.373 (4) | C16—H16B | 0.96 |
C6—H6 | 0.93 | C16—H16C | 0.96 |
C7—C8 | 1.375 (5) | C17—H17A | 0.96 |
C7—H7 | 0.93 | C17—H17B | 0.96 |
C8—C9 | 1.365 (4) | C17—H17C | 0.96 |
C8—H8 | 0.93 | ||
O2—S1—O1 | 119.53 (10) | C4—C9—H9 | 120.6 |
O2—S1—N1 | 107.47 (9) | C15—C10—C11 | 121.3 (2) |
O1—S1—N1 | 106.42 (9) | C15—C10—S1 | 118.94 (18) |
O2—S1—C10 | 108.74 (10) | C11—C10—S1 | 119.72 (18) |
O1—S1—C10 | 108.58 (10) | C10—C11—C12 | 118.0 (3) |
N1—S1—C10 | 105.17 (8) | C10—C11—H11 | 121.0 |
C5—N1—C2 | 107.40 (15) | C12—C11—H11 | 121.0 |
C5—N1—S1 | 122.51 (13) | C13—C12—C11 | 121.2 (3) |
C2—N1—S1 | 125.43 (13) | C13—C12—H12 | 119.4 |
C3—C2—N1 | 108.72 (17) | C11—C12—H12 | 119.4 |
C3—C2—C16 | 127.63 (19) | C12—C13—C14 | 120.0 (3) |
N1—C2—C16 | 123.54 (18) | C12—C13—H13 | 120.0 |
C2—C3—C4 | 108.48 (18) | C14—C13—H13 | 120.0 |
C2—C3—C17 | 127.0 (2) | C13—C14—C15 | 120.3 (3) |
C4—C3—C17 | 124.5 (2) | C13—C14—H14 | 119.8 |
C5—C4—C9 | 119.3 (2) | C15—C14—H14 | 119.8 |
C5—C4—C3 | 108.07 (18) | C10—C15—C14 | 119.1 (3) |
C9—C4—C3 | 132.7 (2) | C10—C15—H15 | 120.4 |
C6—C5—C4 | 121.7 (2) | C14—C15—H15 | 120.4 |
C6—C5—N1 | 131.1 (2) | C2—C16—H16A | 109.5 |
C4—C5—N1 | 107.23 (17) | C2—C16—H16B | 109.5 |
C7—C6—C5 | 117.1 (3) | H16A—C16—H16B | 109.5 |
C7—C6—H6 | 121.4 | C2—C16—H16C | 109.5 |
C5—C6—H6 | 121.4 | H16A—C16—H16C | 109.5 |
C6—C7—C8 | 122.1 (3) | H16B—C16—H16C | 109.5 |
C6—C7—H7 | 119.0 | C3—C17—H17A | 109.5 |
C8—C7—H7 | 119.0 | C3—C17—H17B | 109.5 |
C9—C8—C7 | 121.0 (3) | H17A—C17—H17B | 109.5 |
C9—C8—H8 | 119.5 | C3—C17—H17C | 109.5 |
C7—C8—H8 | 119.5 | H17A—C17—H17C | 109.5 |
C8—C9—C4 | 118.8 (3) | H17B—C17—H17C | 109.5 |
C8—C9—H9 | 120.6 | ||
O2—S1—N1—C5 | 170.86 (15) | C2—N1—C5—C4 | 2.6 (2) |
O1—S1—N1—C5 | 41.69 (17) | S1—N1—C5—C4 | 159.52 (14) |
C10—S1—N1—C5 | −73.40 (16) | C4—C5—C6—C7 | −0.3 (3) |
O2—S1—N1—C2 | −36.42 (18) | N1—C5—C6—C7 | −179.86 (19) |
O1—S1—N1—C2 | −165.58 (15) | C5—C6—C7—C8 | 1.0 (4) |
C10—S1—N1—C2 | 79.32 (17) | C6—C7—C8—C9 | −0.8 (4) |
C5—N1—C2—C3 | −3.2 (2) | C7—C8—C9—C4 | −0.1 (4) |
S1—N1—C2—C3 | −159.27 (14) | C5—C4—C9—C8 | 0.7 (3) |
C5—N1—C2—C16 | −179.53 (18) | C3—C4—C9—C8 | −179.0 (2) |
S1—N1—C2—C16 | 24.4 (3) | O2—S1—C10—C15 | 24.3 (2) |
N1—C2—C3—C4 | 2.5 (2) | O1—S1—C10—C15 | 155.85 (18) |
C16—C2—C3—C4 | 178.6 (2) | N1—S1—C10—C15 | −90.57 (19) |
N1—C2—C3—C17 | −176.6 (2) | O2—S1—C10—C11 | −156.27 (17) |
C16—C2—C3—C17 | −0.4 (4) | O1—S1—C10—C11 | −24.72 (19) |
C2—C3—C4—C5 | −0.9 (2) | N1—S1—C10—C11 | 88.87 (18) |
C17—C3—C4—C5 | 178.2 (2) | C15—C10—C11—C12 | 0.9 (3) |
C2—C3—C4—C9 | 178.8 (2) | S1—C10—C11—C12 | −178.54 (18) |
C17—C3—C4—C9 | −2.0 (4) | C10—C11—C12—C13 | 0.3 (4) |
C9—C4—C5—C6 | −0.5 (3) | C11—C12—C13—C14 | −1.2 (4) |
C3—C4—C5—C6 | 179.25 (18) | C12—C13—C14—C15 | 1.0 (5) |
C9—C4—C5—N1 | 179.13 (18) | C11—C10—C15—C14 | −1.1 (4) |
C3—C4—C5—N1 | −1.1 (2) | S1—C10—C15—C14 | 178.3 (2) |
C2—N1—C5—C6 | −177.85 (19) | C13—C14—C15—C10 | 0.2 (4) |
S1—N1—C5—C6 | −20.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.36 | 2.938 (3) | 120 |
C6—H6···O1i | 0.93 | 2.54 | 3.317 (3) | 141 |
C15—H15···O2 | 0.93 | 2.58 | 2.932 (3) | 103 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C16H15NO2S |
Mr | 285.35 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.8800 (13), 9.6020 (16), 9.9864 (17) |
α, β, γ (°) | 82.210 (3), 81.487 (3), 71.087 (3) |
V (Å3) | 703.8 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.23 × 0.21 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.948, 0.957 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8276, 3284, 2540 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.660 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.145, 1.04 |
No. of reflections | 3284 |
No. of parameters | 183 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.19 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), PLATON (Spek, 2003).
S1—O2 | 1.4166 (16) | S1—C10 | 1.760 (2) |
S1—O1 | 1.4203 (16) | N1—C5 | 1.415 (2) |
S1—N1 | 1.6577 (16) | N1—C2 | 1.436 (2) |
O2—S1—O1 | 119.53 (10) | C5—C4—C9 | 119.3 (2) |
N1—S1—C10 | 105.17 (8) | C6—C5—C4 | 121.7 (2) |
C16—C2—C3—C4 | 178.6 (2) | C17—C3—C4—C5 | 178.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1 | 0.93 | 2.36 | 2.938 (3) | 120 |
C6—H6···O1i | 0.93 | 2.54 | 3.317 (3) | 141 |
C15—H15···O2 | 0.93 | 2.58 | 2.932 (3) | 103 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Indole compounds can be used as bioactive drugs (Stevenson et al., 2000). Indole derivatives exhibit anti-allergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). Indoles have also been proved to display high aldose reductase inhibitory activity (Rajeswaran et al., 1999). In view of this biological importance, an X-ray study of the title compound, (I), was carrried out.
A ZORTEP (Zsolnai, 1997) plot of the molecule is shown in Fig. 1. The longer C—N distances in the indole moiety are due to the electron-withdrawing character of the phenylsulfonyl group (Govindasamy et al., 1997, 1998). The endocyclic bond angles at atoms C4 and C5 deviate from the normal value as a result of the fusion of smaller pyrrole and benzene rings (Sethusankar et al., 2002). The widening of the O—S—O and the resultant narrowing of the N—S—C angles (Table 1) from the ideal tetrahedral value are attributed to the Thorpe–Ingold effect (Bassindale, 1984). The dihedral angle between the C10–C15 phenyl ring and the indole ring system is 86.80 (6)°.
In the crystal structure, the molecules form centrosymmetric dimers via C—H···O hydrogen bonds (Table 2 and Fig. 2). In addition, a π–π stacking interaction involving the pyrrole ring (centroid Cg1) with a Cg1···Cg1(1 − x, 1 − y, −z) distance of 3.594 (2) Å is observed.