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In the title compound, C
24H
17N
3O, the dihedral angles between the planes of the two indole ring systems and the oxindole group are 77.7 (1) and 71.9 (1)°. The molecular packing in the crystal structure is stabilized by an intermolecular N—H
O hydrogen bond.
Supporting information
CCDC reference: 287459
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.050
- wR factor = 0.134
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2 ... ?
PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3 ... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
A mixture of indole (2.5 mmol), isatin (1.25 mmol) and gadolinium trifluoromethanesulfonate (55 mg, 0.093 mmol) was stirred in acetonitrile (6 ml). After completion of the reaction, water was added to quench the reaction, and the product was extracted with ethylacetate (3 × 10 ml) and washed with aqueous sodium bicarbonate and a sodium chloride solution; the combined organic layers were dried using anhydrous Na2SO4 and filtered, and the solvent was evaporated. The crude products were purified by column chromatography and eluted with an ethylacetate and hexane (3:1) mixture to afford the title compound. To obtain diffraction quality crystals, recrystallization was carried out using an ethylacetate and hexane (1:1) mixture.
The H atoms were positioned geometrically and were treated as riding on their parent C atoms with C—H distances of 0.93 Å, N—H distances of 0.86 Å and Uiso(H) = 1.2Ueq(C,N).
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: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
3,3-Bis(1
H-indol-3-yl)indolin-2-one
top
Crystal data top
C24H17N3O | F(000) = 1520 |
Mr = 363.41 | Dx = 1.332 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 9828 reflections |
a = 24.0578 (12) Å | θ = 2.5–26.6° |
b = 10.2342 (5) Å | µ = 0.08 mm−1 |
c = 18.1597 (9) Å | T = 293 K |
β = 125.861 (1)° | Block, colourless |
V = 3623.6 (3) Å3 | 0.24 × 0.22 × 0.20 mm |
Z = 8 | |
Data collection top
Bruker SMART APEX area-detector diffractometer | 3677 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 28.0°, θmin = 2.1° |
ω scans | h = −31→31 |
20359 measured reflections | k = −13→13 |
4278 independent reflections | l = −23→23 |
Refinement top
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0696P)2 + 1.847P] where P = (Fo2 + 2Fc2)/3 |
4278 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C24H17N3O | V = 3623.6 (3) Å3 |
Mr = 363.41 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 24.0578 (12) Å | µ = 0.08 mm−1 |
b = 10.2342 (5) Å | T = 293 K |
c = 18.1597 (9) Å | 0.24 × 0.22 × 0.20 mm |
β = 125.861 (1)° | |
Data collection top
Bruker SMART APEX area-detector diffractometer | 3677 reflections with I > 2σ(I) |
20359 measured reflections | Rint = 0.023 |
4278 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.31 e Å−3 |
4278 reflections | Δρmin = −0.22 e Å−3 |
253 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.36680 (6) | 0.34810 (10) | 0.47802 (8) | 0.0527 (3) | |
N1 | 0.19426 (7) | 0.10835 (13) | 0.42508 (9) | 0.0478 (3) | |
H1 | 0.1786 | 0.1034 | 0.4572 | 0.057* | |
N2 | 0.49456 (7) | −0.01347 (15) | 0.60660 (10) | 0.0585 (4) | |
H2 | 0.5370 | −0.0108 | 0.6522 | 0.070* | |
N3 | 0.35915 (7) | 0.31588 (11) | 0.34777 (9) | 0.0442 (3) | |
H3 | 0.3673 | 0.3948 | 0.3404 | 0.053* | |
C1 | 0.15557 (8) | 0.11366 (14) | 0.33255 (11) | 0.0421 (3) | |
C2 | 0.08467 (9) | 0.11248 (19) | 0.26935 (14) | 0.0606 (5) | |
H2A | 0.0560 | 0.1068 | 0.2880 | 0.073* | |
C3 | 0.05800 (9) | 0.11981 (18) | 0.17889 (14) | 0.0613 (5) | |
H3A | 0.0107 | 0.1180 | 0.1356 | 0.074* | |
C4 | 0.10087 (8) | 0.12999 (15) | 0.15087 (11) | 0.0497 (4) | |
H4 | 0.0816 | 0.1363 | 0.0892 | 0.060* | |
C5 | 0.17132 (7) | 0.13091 (13) | 0.21295 (10) | 0.0382 (3) | |
H5 | 0.1992 | 0.1380 | 0.1933 | 0.046* | |
C6 | 0.20042 (7) | 0.12108 (12) | 0.30600 (10) | 0.0335 (3) | |
C7 | 0.26870 (7) | 0.11893 (12) | 0.38898 (9) | 0.0320 (3) | |
C8 | 0.26183 (8) | 0.11228 (14) | 0.45823 (10) | 0.0397 (3) | |
H8 | 0.2982 | 0.1106 | 0.5196 | 0.048* | |
C9 | 0.45245 (8) | −0.11961 (16) | 0.58086 (10) | 0.0454 (4) | |
C10 | 0.46520 (9) | −0.24451 (19) | 0.61847 (12) | 0.0602 (5) | |
H10 | 0.5083 | −0.2671 | 0.6698 | 0.072* | |
C11 | 0.41269 (10) | −0.33243 (18) | 0.57782 (13) | 0.0598 (5) | |
H11 | 0.4203 | −0.4164 | 0.6015 | 0.072* | |
C12 | 0.34805 (9) | −0.29896 (15) | 0.50172 (12) | 0.0517 (4) | |
H12 | 0.3131 | −0.3607 | 0.4756 | 0.062* | |
C13 | 0.33481 (7) | −0.17591 (14) | 0.46412 (9) | 0.0393 (3) | |
H13 | 0.2913 | −0.1548 | 0.4131 | 0.047* | |
C14 | 0.38741 (7) | −0.08311 (13) | 0.50346 (9) | 0.0344 (3) | |
C15 | 0.39265 (7) | 0.05122 (13) | 0.48435 (9) | 0.0343 (3) | |
C16 | 0.45856 (8) | 0.08765 (17) | 0.54850 (11) | 0.0502 (4) | |
H16 | 0.4766 | 0.1698 | 0.5523 | 0.060* | |
C17 | 0.33740 (7) | 0.13018 (12) | 0.40370 (9) | 0.0316 (3) | |
C18 | 0.35667 (7) | 0.27795 (13) | 0.41715 (10) | 0.0379 (3) | |
C19 | 0.34700 (7) | 0.21277 (13) | 0.28932 (9) | 0.0358 (3) | |
C20 | 0.34793 (8) | 0.21436 (16) | 0.21404 (10) | 0.0459 (4) | |
H20 | 0.3555 | 0.2913 | 0.1939 | 0.055* | |
C21 | 0.33709 (9) | 0.09674 (17) | 0.16975 (11) | 0.0508 (4) | |
H21 | 0.3378 | 0.0945 | 0.1192 | 0.061* | |
C22 | 0.32518 (9) | −0.01725 (16) | 0.19913 (10) | 0.0475 (4) | |
H22 | 0.3181 | −0.0950 | 0.1683 | 0.057* | |
C23 | 0.32362 (7) | −0.01674 (13) | 0.27478 (9) | 0.0380 (3) | |
H23 | 0.3154 | −0.0934 | 0.2945 | 0.046* | |
C24 | 0.33440 (6) | 0.09928 (13) | 0.31944 (9) | 0.0315 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0733 (8) | 0.0406 (6) | 0.0699 (7) | −0.0152 (5) | 0.0562 (7) | −0.0197 (5) |
N1 | 0.0508 (7) | 0.0574 (8) | 0.0560 (8) | 0.0045 (6) | 0.0429 (7) | 0.0089 (6) |
N2 | 0.0322 (6) | 0.0699 (10) | 0.0507 (8) | −0.0035 (6) | 0.0116 (6) | 0.0013 (7) |
N3 | 0.0614 (8) | 0.0298 (6) | 0.0571 (8) | −0.0066 (5) | 0.0435 (7) | −0.0011 (5) |
C1 | 0.0430 (8) | 0.0380 (7) | 0.0562 (9) | 0.0056 (6) | 0.0352 (7) | 0.0106 (6) |
C2 | 0.0409 (8) | 0.0711 (12) | 0.0782 (12) | 0.0112 (8) | 0.0396 (9) | 0.0283 (9) |
C3 | 0.0344 (8) | 0.0641 (11) | 0.0722 (12) | 0.0063 (7) | 0.0238 (8) | 0.0257 (9) |
C4 | 0.0457 (8) | 0.0438 (8) | 0.0481 (9) | 0.0040 (6) | 0.0211 (7) | 0.0111 (7) |
C5 | 0.0413 (7) | 0.0319 (7) | 0.0434 (7) | 0.0018 (5) | 0.0261 (6) | 0.0046 (5) |
C6 | 0.0367 (7) | 0.0245 (6) | 0.0454 (7) | 0.0021 (5) | 0.0275 (6) | 0.0034 (5) |
C7 | 0.0378 (7) | 0.0278 (6) | 0.0384 (7) | 0.0003 (5) | 0.0267 (6) | 0.0003 (5) |
C8 | 0.0444 (8) | 0.0421 (7) | 0.0429 (7) | 0.0010 (6) | 0.0313 (7) | 0.0020 (6) |
C9 | 0.0359 (7) | 0.0550 (9) | 0.0412 (8) | 0.0031 (6) | 0.0203 (6) | 0.0014 (6) |
C10 | 0.0514 (10) | 0.0661 (11) | 0.0518 (9) | 0.0200 (8) | 0.0238 (8) | 0.0194 (8) |
C11 | 0.0693 (11) | 0.0463 (9) | 0.0615 (10) | 0.0119 (8) | 0.0370 (9) | 0.0174 (8) |
C12 | 0.0606 (10) | 0.0407 (8) | 0.0540 (9) | −0.0035 (7) | 0.0337 (8) | 0.0025 (7) |
C13 | 0.0417 (7) | 0.0389 (7) | 0.0357 (7) | −0.0023 (6) | 0.0218 (6) | −0.0006 (6) |
C14 | 0.0356 (6) | 0.0393 (7) | 0.0314 (6) | 0.0023 (5) | 0.0214 (5) | −0.0001 (5) |
C15 | 0.0346 (6) | 0.0379 (7) | 0.0350 (6) | −0.0040 (5) | 0.0230 (6) | −0.0044 (5) |
C16 | 0.0413 (8) | 0.0510 (9) | 0.0538 (9) | −0.0109 (7) | 0.0254 (7) | −0.0071 (7) |
C17 | 0.0380 (7) | 0.0287 (6) | 0.0368 (6) | −0.0031 (5) | 0.0267 (6) | −0.0034 (5) |
C18 | 0.0420 (7) | 0.0331 (7) | 0.0497 (8) | −0.0044 (5) | 0.0331 (7) | −0.0051 (6) |
C19 | 0.0364 (7) | 0.0354 (7) | 0.0413 (7) | 0.0000 (5) | 0.0259 (6) | 0.0017 (5) |
C20 | 0.0520 (9) | 0.0499 (9) | 0.0449 (8) | −0.0039 (7) | 0.0335 (7) | 0.0070 (7) |
C21 | 0.0599 (10) | 0.0642 (10) | 0.0396 (8) | −0.0024 (8) | 0.0355 (8) | −0.0010 (7) |
C22 | 0.0598 (9) | 0.0480 (9) | 0.0424 (8) | −0.0019 (7) | 0.0343 (7) | −0.0089 (6) |
C23 | 0.0451 (7) | 0.0347 (7) | 0.0399 (7) | −0.0002 (5) | 0.0281 (6) | −0.0004 (5) |
C24 | 0.0311 (6) | 0.0350 (6) | 0.0339 (6) | 0.0010 (5) | 0.0221 (5) | 0.0013 (5) |
Geometric parameters (Å, º) top
O1—C18 | 1.217 (2) | C9—C14 | 1.4096 (19) |
N1—C1 | 1.364 (2) | C10—C11 | 1.363 (3) |
N1—C8 | 1.3637 (19) | C10—H10 | 0.9300 |
N1—H1 | 0.8600 | C11—C12 | 1.388 (3) |
N2—C16 | 1.365 (2) | C11—H11 | 0.9300 |
N2—C9 | 1.367 (2) | C12—C13 | 1.378 (2) |
N2—H2 | 0.8600 | C12—H12 | 0.9300 |
N3—C18 | 1.3526 (18) | C13—C14 | 1.3980 (19) |
N3—C19 | 1.4007 (18) | C13—H13 | 0.9300 |
N3—H3 | 0.8600 | C14—C15 | 1.4415 (19) |
C1—C2 | 1.390 (2) | C15—C16 | 1.359 (2) |
C1—C6 | 1.4186 (19) | C15—C17 | 1.511 (2) |
C2—C3 | 1.372 (3) | C16—H16 | 0.9300 |
C2—H2A | 0.9300 | C17—C24 | 1.5221 (17) |
C3—C4 | 1.396 (3) | C17—C18 | 1.5585 (18) |
C3—H3A | 0.9300 | C19—C20 | 1.380 (2) |
C4—C5 | 1.380 (2) | C19—C24 | 1.3909 (18) |
C4—H4 | 0.9300 | C20—C21 | 1.385 (2) |
C5—C6 | 1.403 (2) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—C22 | 1.381 (2) |
C6—C7 | 1.4384 (19) | C21—H21 | 0.9300 |
C7—C8 | 1.3628 (18) | C22—C23 | 1.3961 (19) |
C7—C17 | 1.516 (2) | C22—H22 | 0.9300 |
C8—H8 | 0.9300 | C23—C24 | 1.3743 (18) |
C9—C10 | 1.396 (2) | C23—H23 | 0.9300 |
| | | |
C1—N1—C8 | 108.63 (12) | C13—C12—C11 | 121.18 (16) |
C1—N1—H1 | 125.7 | C13—C12—H12 | 119.4 |
C8—N1—H1 | 125.7 | C11—C12—H12 | 119.4 |
C16—N2—C9 | 109.30 (13) | C12—C13—C14 | 119.37 (14) |
C16—N2—H2 | 125.4 | C12—C13—H13 | 120.3 |
C9—N2—H2 | 125.4 | C14—C13—H13 | 120.3 |
C18—N3—C19 | 112.72 (11) | C13—C14—C9 | 118.25 (13) |
C18—N3—H3 | 123.6 | C13—C14—C15 | 134.88 (13) |
C19—N3—H3 | 123.6 | C9—C14—C15 | 106.87 (12) |
N1—C1—C2 | 129.67 (15) | C16—C15—C14 | 106.15 (13) |
N1—C1—C6 | 108.35 (13) | C16—C15—C17 | 127.32 (13) |
C2—C1—C6 | 121.98 (15) | C14—C15—C17 | 126.29 (11) |
C3—C2—C1 | 118.36 (15) | C15—C16—N2 | 110.37 (14) |
C3—C2—H2A | 120.8 | C15—C16—H16 | 124.8 |
C1—C2—H2A | 120.8 | N2—C16—H16 | 124.8 |
C2—C3—C4 | 120.91 (16) | C15—C17—C7 | 112.29 (10) |
C2—C3—H3A | 119.5 | C15—C17—C24 | 111.10 (10) |
C4—C3—H3A | 119.5 | C7—C17—C24 | 113.71 (11) |
C5—C4—C3 | 121.24 (16) | C15—C17—C18 | 110.79 (11) |
C5—C4—H4 | 119.4 | C7—C17—C18 | 107.14 (10) |
C3—C4—H4 | 119.4 | C24—C17—C18 | 101.17 (10) |
C4—C5—C6 | 119.40 (14) | O1—C18—N3 | 125.60 (13) |
C4—C5—H5 | 120.3 | O1—C18—C17 | 126.71 (13) |
C6—C5—H5 | 120.3 | N3—C18—C17 | 107.69 (11) |
C5—C6—C1 | 118.08 (13) | C20—C19—C24 | 122.21 (13) |
C5—C6—C7 | 136.10 (12) | C20—C19—N3 | 128.64 (13) |
C1—C6—C7 | 105.80 (12) | C24—C19—N3 | 109.14 (12) |
C8—C7—C6 | 106.63 (12) | C19—C20—C21 | 117.26 (13) |
C8—C7—C17 | 123.37 (12) | C19—C20—H20 | 121.4 |
C6—C7—C17 | 129.90 (11) | C21—C20—H20 | 121.4 |
C7—C8—N1 | 110.59 (13) | C22—C21—C20 | 121.41 (13) |
C7—C8—H8 | 124.7 | C22—C21—H21 | 119.3 |
N1—C8—H8 | 124.7 | C20—C21—H21 | 119.3 |
N2—C9—C10 | 130.82 (15) | C21—C22—C23 | 120.55 (14) |
N2—C9—C14 | 107.32 (14) | C21—C22—H22 | 119.7 |
C10—C9—C14 | 121.86 (15) | C23—C22—H22 | 119.7 |
C11—C10—C9 | 118.11 (15) | C24—C23—C22 | 118.65 (13) |
C11—C10—H10 | 120.9 | C24—C23—H23 | 120.7 |
C9—C10—H10 | 120.9 | C22—C23—H23 | 120.7 |
C10—C11—C12 | 121.24 (16) | C23—C24—C19 | 119.91 (12) |
C10—C11—H11 | 119.4 | C23—C24—C17 | 130.86 (12) |
C12—C11—H11 | 119.4 | C19—C24—C17 | 109.21 (11) |
| | | |
C8—N1—C1—C2 | −179.99 (16) | C16—C15—C17—C7 | −137.91 (14) |
C8—N1—C1—C6 | 0.08 (16) | C14—C15—C17—C7 | 48.44 (17) |
N1—C1—C2—C3 | 179.55 (16) | C16—C15—C17—C24 | 93.5 (2) |
C6—C1—C2—C3 | −0.5 (3) | C14—C15—C17—C24 | −80.16 (15) |
C1—C2—C3—C4 | −0.8 (3) | C16—C15—C17—C18 | −18.15 (19) |
C2—C3—C4—C5 | 1.0 (3) | C14—C15—C17—C18 | 168.21 (12) |
C3—C4—C5—C6 | 0.2 (2) | C8—C7—C17—C15 | 37.08 (17) |
C4—C5—C6—C1 | −1.48 (19) | C6—C7—C17—C15 | −147.15 (13) |
C4—C5—C6—C7 | −179.76 (14) | C8—C7—C17—C24 | 164.3 (1) |
N1—C1—C6—C5 | −178.37 (12) | C6—C7—C17—C24 | −19.93 (18) |
C2—C1—C6—C5 | 1.7 (2) | C8—C7—C17—C18 | −84.79 (15) |
N1—C1—C6—C7 | 0.39 (15) | C6—C7—C17—C18 | 90.98 (15) |
C2—C1—C6—C7 | −179.55 (14) | C19—N3—C18—O1 | 178.41 (14) |
C5—C6—C7—C8 | 177.71 (14) | C19—N3—C18—C17 | −2.54 (16) |
C1—C6—C7—C8 | −0.71 (14) | C15—C17—C18—O1 | −60.28 (18) |
C5—C6—C7—C17 | 1.4 (2) | C7—C17—C18—O1 | 62.52 (19) |
C1—C6—C7—C17 | −177.02 (12) | C24—C17—C18—O1 | −178.16 (15) |
C6—C7—C8—N1 | 0.79 (16) | C15—C17—C18—N3 | 120.68 (12) |
C17—C7—C8—N1 | 177.40 (12) | C7—C17—C18—N3 | −116.51 (12) |
C1—N1—C8—C7 | −0.55 (17) | C24—C17—C18—N3 | 2.81 (14) |
C16—N2—C9—C10 | −179.75 (18) | C18—N3—C19—C20 | −177.52 (15) |
C16—N2—C9—C14 | −0.05 (19) | C18—N3—C19—C24 | 1.10 (17) |
N2—C9—C10—C11 | −179.91 (18) | C24—C19—C20—C21 | −1.3 (2) |
C14—C9—C10—C11 | 0.4 (3) | N3—C19—C20—C21 | 177.16 (15) |
C9—C10—C11—C12 | −0.7 (3) | C19—C20—C21—C22 | 0.6 (2) |
C10—C11—C12—C13 | 0.5 (3) | C20—C21—C22—C23 | 0.1 (3) |
C11—C12—C13—C14 | −0.1 (2) | C21—C22—C23—C24 | −0.2 (2) |
C12—C13—C14—C9 | −0.1 (2) | C22—C23—C24—C19 | −0.4 (2) |
C12—C13—C14—C15 | −179.42 (15) | C22—C23—C24—C17 | −178.43 (14) |
N2—C9—C14—C13 | −179.78 (13) | C20—C19—C24—C23 | 1.2 (2) |
C10—C9—C14—C13 | 0.0 (2) | N3—C19—C24—C23 | −177.49 (12) |
N2—C9—C14—C15 | −0.29 (16) | C20—C19—C24—C17 | 179.62 (13) |
C10—C9—C14—C15 | 179.44 (15) | N3—C19—C24—C17 | 0.90 (15) |
C13—C14—C15—C16 | 179.88 (15) | C15—C17—C24—C23 | 58.30 (18) |
C9—C14—C15—C16 | 0.52 (15) | C7—C17—C24—C23 | −69.54 (18) |
C13—C14—C15—C17 | −5.4 (2) | C18—C17—C24—C23 | 175.95 (14) |
C9—C14—C15—C17 | 175.26 (12) | C15—C17—C24—C19 | −119.85 (12) |
C14—C15—C16—N2 | −0.56 (17) | C7—C17—C24—C19 | 112.30 (12) |
C17—C15—C16—N2 | −175.23 (13) | C18—C17—C24—C19 | −2.20 (14) |
C9—N2—C16—C15 | 0.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.08 | 2.913 (2) | 162 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |
Experimental details
Crystal data |
Chemical formula | C24H17N3O |
Mr | 363.41 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 24.0578 (12), 10.2342 (5), 18.1597 (9) |
β (°) | 125.861 (1) |
V (Å3) | 3623.6 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.24 × 0.22 × 0.20 |
|
Data collection |
Diffractometer | Bruker SMART APEX area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20359, 4278, 3677 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.661 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.134, 1.05 |
No. of reflections | 4278 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.22 |
Selected geometric parameters (Å, º) topO1—C18 | 1.217 (2) | C15—C17 | 1.511 (2) |
C7—C17 | 1.516 (2) | | |
| | | |
C16—C15—C17—C24 | 93.5 (2) | C8—C7—C17—C24 | 164.3 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.08 | 2.913 (2) | 162 |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |
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Indole, being an integral part of many natural products of therapeutic importance, possesses potentially reactive sites for a variety of chemical reactions to generate molecular diversity (Farhanullah et al., 2004). Indole derivatives are identified as interfering with a G protein-independent signaling pathway of CRTH2 receptor (Mathiesen et al., 2005). These derivatives also possess antiviral (Sechi et al., 2004) and antimalarial (Agarwal et al., 2005) activities. Oxindole derivatives possess antifungal activity (Strigacova et al., 2001) and act as orally active potent growth hormone secretagogues (Tokunaga et al., 2001). In view of its importance and to obtain more detailed information about the structural conformation of the molecule, the structure of the title compound, (I), was determined.
Compound (I) (Fig. 1) consists of two indole groups (A and B) and one oxindole group (C). Selected geometric parameters are presented in Table 1. The geometry of the indole rings is comparable to those reported for other indole derivatives (Karthick et al., 2005; Sonar et al., 2005).
The two indole rign systems are oriented with a dihedral angle of 68.4 (1)° with respect to each other. The dihedral angles between the oxindole plane and the indole planes (A and B) are 77.7 (1) and 71.9 (1)°, respectively.
In the crystal structure, two inversion-related molecules are linked via an N1—H1···O1i hydrogen bond (Table 2). As a result, an R22(14) graph-set dimer is formed.