Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013125/cf6102sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013125/cf6102Isup2.hkl |
CCDC reference: 172210
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.064
- wR factor = 0.169
- Data-to-parameter ratio = 12.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound, (I), was prepared by the photoinduced reaction (Peterno-Büchi reaction; Arnold, 1968) of a benzene solution (40 ml) of 1-acetylisatin (0.05 M) and 2-phenylbenzofuran (0.1 M) with a Pyrex-filtered light of a medium-pressure mercury lamp (500 W, λ > 400 nm). The reaction was carried out under constant nitrogen purging. After irradiation, the solvent was removed in vacuo and the residue was separated by column chromatography. Compound (I) was obtained as the main diastereomer of the product and was recrystallized from a mixture of petroleum ether and ethyl acetate.
After checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on the parent C atoms and refined isotropically. Due to a large fraction of weak data at higher angles, the 2θ maximum was limited to 50°.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C24H17NO4 | F(000) = 400 |
Mr = 383.39 | Dx = 1.370 Mg m−3 |
Triclinic, P1 | Melting point: 477 K |
a = 9.2136 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2904 (3) Å | Cell parameters from 3227 reflections |
c = 10.9603 (3) Å | θ = 2.0–28.3° |
α = 68.119 (1)° | µ = 0.09 mm−1 |
β = 80.830 (1)° | T = 293 K |
γ = 75.083 (1)° | Slab, colourless |
V = 929.47 (4) Å3 | 0.36 × 0.28 × 0.18 mm |
Z = 2 |
Siemens SMART CCD area-detector diffractometer | 2148 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
Detector resolution: 8.33 pixels mm-1 | h = −10→9 |
ω scans | k = −12→8 |
5322 measured reflections | l = −13→12 |
3231 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.169 | w = 1/[σ2(Fo2) + (0.0957P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
3231 reflections | Δρmax = 0.29 e Å−3 |
264 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.081 (8) |
C24H17NO4 | γ = 75.083 (1)° |
Mr = 383.39 | V = 929.47 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.2136 (2) Å | Mo Kα radiation |
b = 10.2904 (3) Å | µ = 0.09 mm−1 |
c = 10.9603 (3) Å | T = 293 K |
α = 68.119 (1)° | 0.36 × 0.28 × 0.18 mm |
β = 80.830 (1)° |
Siemens SMART CCD area-detector diffractometer | 2148 reflections with I > 2σ(I) |
5322 measured reflections | Rint = 0.048 |
3231 independent reflections |
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.29 e Å−3 |
3231 reflections | Δρmin = −0.31 e Å−3 |
264 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 | ||
O1 | 0.4871 (2) | 0.1249 (3) | 0.2689 (2) | 0.0686 (7) | |
O2 | 0.6613 (2) | 0.2085 (2) | 0.54998 (19) | 0.0495 (5) | |
O3 | 0.38393 (19) | 0.38228 (18) | 0.64948 (16) | 0.0403 (5) | |
O4 | 0.3178 (2) | 0.3650 (2) | 0.87177 (18) | 0.0472 (5) | |
N1 | 0.4705 (2) | 0.1806 (2) | 0.45250 (19) | 0.0332 (5) | |
C1 | 0.5315 (3) | 0.2088 (3) | 0.5471 (2) | 0.0336 (6) | |
C2 | 0.3150 (3) | 0.1753 (3) | 0.4911 (2) | 0.0328 (6) | |
C3 | 0.2134 (3) | 0.1497 (3) | 0.4279 (3) | 0.0437 (7) | |
H3A | 0.2424 | 0.1266 | 0.3520 | 0.052* | |
C4 | 0.0660 (3) | 0.1599 (3) | 0.4823 (3) | 0.0484 (7) | |
H4A | −0.0050 | 0.1429 | 0.4417 | 0.058* | |
C5 | 0.0217 (3) | 0.1945 (3) | 0.5946 (3) | 0.0509 (8) | |
H5A | −0.0782 | 0.2012 | 0.6283 | 0.061* | |
C6 | 0.1242 (3) | 0.2193 (3) | 0.6570 (3) | 0.0463 (7) | |
H6A | 0.0946 | 0.2429 | 0.7327 | 0.056* | |
C7 | 0.2721 (3) | 0.2086 (3) | 0.6059 (2) | 0.0357 (6) | |
C8 | 0.4033 (3) | 0.2369 (3) | 0.6491 (2) | 0.0347 (6) | |
C9 | 0.4514 (3) | 0.1737 (3) | 0.7929 (2) | 0.0329 (6) | |
H9A | 0.5527 | 0.1125 | 0.8058 | 0.039* | |
C10 | 0.3338 (3) | 0.1269 (3) | 0.9002 (2) | 0.0355 (6) | |
C11 | 0.2916 (3) | −0.0022 (3) | 0.9607 (2) | 0.0432 (7) | |
H11A | 0.3401 | −0.0808 | 0.9361 | 0.052* | |
C12 | 0.1750 (3) | −0.0135 (4) | 1.0594 (3) | 0.0560 (8) | |
H12A | 0.1449 | −0.1003 | 1.1009 | 0.067* | |
C13 | 0.1040 (4) | 0.1030 (4) | 1.0961 (3) | 0.0621 (9) | |
H13A | 0.0266 | 0.0935 | 1.1625 | 0.075* | |
C14 | 0.1454 (3) | 0.2346 (4) | 1.0360 (3) | 0.0545 (8) | |
H14A | 0.0969 | 0.3133 | 1.0604 | 0.065* | |
C15 | 0.2618 (3) | 0.2433 (3) | 0.9387 (2) | 0.0410 (7) | |
C16 | 0.4378 (3) | 0.3324 (3) | 0.7788 (2) | 0.0378 (7) | |
C17 | 0.5684 (3) | 0.3908 (3) | 0.7850 (2) | 0.0375 (6) | |
C18 | 0.6015 (3) | 0.3906 (3) | 0.9045 (3) | 0.0468 (7) | |
H18A | 0.5379 | 0.3608 | 0.9795 | 0.056* | |
C19 | 0.7282 (4) | 0.4345 (3) | 0.9125 (3) | 0.0572 (8) | |
H19A | 0.7497 | 0.4333 | 0.9930 | 0.069* | |
C20 | 0.8231 (4) | 0.4800 (3) | 0.8018 (3) | 0.0559 (8) | |
H20A | 0.9085 | 0.5090 | 0.8077 | 0.067* | |
C21 | 0.7908 (3) | 0.4822 (3) | 0.6834 (3) | 0.0494 (8) | |
H21A | 0.8550 | 0.5122 | 0.6089 | 0.059* | |
C22 | 0.6631 (3) | 0.4400 (3) | 0.6737 (3) | 0.0444 (7) | |
H22A | 0.6407 | 0.4446 | 0.5922 | 0.053* | |
C23 | 0.5448 (3) | 0.1673 (3) | 0.3331 (3) | 0.0431 (7) | |
C24 | 0.6938 (3) | 0.2084 (4) | 0.2925 (3) | 0.0580 (9) | |
H24C | 0.7254 | 0.2086 | 0.2046 | 0.087* | |
H24A | 0.7668 | 0.1407 | 0.3519 | 0.087* | |
H24B | 0.6853 | 0.3025 | 0.2947 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0626 (14) | 0.113 (2) | 0.0514 (13) | −0.0160 (13) | −0.0005 (11) | −0.0565 (14) |
O2 | 0.0356 (12) | 0.0732 (14) | 0.0490 (12) | −0.0110 (9) | 0.0006 (9) | −0.0336 (11) |
O3 | 0.0535 (11) | 0.0343 (10) | 0.0319 (10) | −0.0038 (8) | −0.0086 (8) | −0.0118 (8) |
O4 | 0.0573 (12) | 0.0472 (12) | 0.0394 (11) | −0.0095 (9) | 0.0094 (9) | −0.0240 (9) |
N1 | 0.0371 (12) | 0.0384 (12) | 0.0245 (11) | −0.0053 (9) | −0.0015 (9) | −0.0135 (9) |
C1 | 0.0369 (15) | 0.0363 (15) | 0.0285 (13) | −0.0059 (10) | −0.0028 (11) | −0.0134 (11) |
C2 | 0.0392 (15) | 0.0333 (14) | 0.0242 (13) | −0.0058 (11) | −0.0053 (11) | −0.0083 (11) |
C3 | 0.0491 (17) | 0.0462 (17) | 0.0385 (15) | −0.0082 (12) | −0.0071 (13) | −0.0178 (13) |
C4 | 0.0452 (17) | 0.0501 (18) | 0.0546 (18) | −0.0137 (13) | −0.0153 (14) | −0.0163 (14) |
C5 | 0.0377 (16) | 0.064 (2) | 0.0481 (18) | −0.0119 (13) | −0.0034 (13) | −0.0149 (15) |
C6 | 0.0390 (16) | 0.0587 (19) | 0.0390 (16) | −0.0063 (13) | −0.0020 (12) | −0.0175 (14) |
C7 | 0.0370 (14) | 0.0372 (15) | 0.0306 (14) | −0.0046 (11) | −0.0053 (11) | −0.0103 (11) |
C8 | 0.0402 (15) | 0.0367 (15) | 0.0281 (13) | −0.0043 (11) | −0.0044 (11) | −0.0142 (11) |
C9 | 0.0404 (14) | 0.0377 (15) | 0.0226 (12) | −0.0079 (11) | −0.0038 (10) | −0.0125 (11) |
C10 | 0.0431 (15) | 0.0432 (16) | 0.0201 (12) | −0.0087 (11) | −0.0054 (11) | −0.0102 (11) |
C11 | 0.0546 (18) | 0.0438 (17) | 0.0309 (14) | −0.0132 (13) | −0.0053 (13) | −0.0099 (12) |
C12 | 0.060 (2) | 0.070 (2) | 0.0394 (16) | −0.0295 (16) | 0.0032 (15) | −0.0131 (16) |
C13 | 0.056 (2) | 0.091 (3) | 0.0418 (17) | −0.0266 (18) | 0.0118 (15) | −0.0244 (18) |
C14 | 0.0515 (18) | 0.074 (2) | 0.0436 (17) | −0.0108 (15) | 0.0088 (14) | −0.0328 (16) |
C15 | 0.0460 (16) | 0.0508 (18) | 0.0284 (14) | −0.0110 (13) | −0.0023 (12) | −0.0158 (13) |
C16 | 0.0494 (16) | 0.0400 (16) | 0.0244 (13) | −0.0052 (12) | −0.0022 (11) | −0.0150 (11) |
C17 | 0.0516 (16) | 0.0296 (14) | 0.0325 (14) | −0.0088 (11) | −0.0025 (12) | −0.0122 (11) |
C18 | 0.066 (2) | 0.0441 (17) | 0.0354 (15) | −0.0178 (14) | −0.0022 (13) | −0.0157 (13) |
C19 | 0.077 (2) | 0.060 (2) | 0.0423 (17) | −0.0212 (16) | −0.0138 (16) | −0.0189 (15) |
C20 | 0.065 (2) | 0.0475 (19) | 0.059 (2) | −0.0215 (15) | −0.0082 (16) | −0.0154 (15) |
C21 | 0.0581 (19) | 0.0396 (17) | 0.0468 (17) | −0.0162 (13) | 0.0037 (14) | −0.0101 (13) |
C22 | 0.0611 (19) | 0.0374 (16) | 0.0325 (14) | −0.0115 (13) | −0.0025 (13) | −0.0096 (12) |
C23 | 0.0483 (17) | 0.0529 (18) | 0.0257 (14) | −0.0021 (13) | −0.0022 (12) | −0.0170 (13) |
C24 | 0.056 (2) | 0.082 (2) | 0.0345 (16) | −0.0188 (16) | 0.0116 (14) | −0.0216 (16) |
O1—C23 | 1.199 (3) | C10—C15 | 1.391 (4) |
O2—C1 | 1.201 (3) | C11—C12 | 1.393 (4) |
O3—C16 | 1.439 (3) | C11—H11A | 0.930 |
O3—C8 | 1.462 (3) | C12—C13 | 1.378 (4) |
O4—C15 | 1.378 (3) | C12—H12A | 0.930 |
O4—C16 | 1.442 (3) | C13—C14 | 1.390 (4) |
N1—C1 | 1.403 (3) | C13—H13A | 0.930 |
N1—C23 | 1.414 (3) | C14—C15 | 1.382 (4) |
N1—C2 | 1.437 (3) | C14—H14A | 0.930 |
C1—C8 | 1.541 (3) | C16—C17 | 1.497 (4) |
C2—C3 | 1.376 (4) | C17—C18 | 1.390 (4) |
C2—C7 | 1.396 (3) | C17—C22 | 1.391 (4) |
C3—C4 | 1.388 (4) | C18—C19 | 1.381 (4) |
C3—H3A | 0.930 | C18—H18A | 0.930 |
C4—C5 | 1.379 (4) | C19—C20 | 1.380 (4) |
C4—H4A | 0.930 | C19—H19A | 0.930 |
C5—C6 | 1.373 (4) | C20—C21 | 1.367 (4) |
C5—H5A | 0.930 | C20—H20A | 0.930 |
C6—C7 | 1.382 (4) | C21—C22 | 1.386 (4) |
C6—H6A | 0.930 | C21—H21A | 0.930 |
C7—C8 | 1.495 (3) | C22—H22A | 0.930 |
C8—C9 | 1.553 (3) | C23—C24 | 1.492 (4) |
C9—C10 | 1.493 (3) | C24—H24C | 0.960 |
C9—C16 | 1.555 (3) | C24—H24A | 0.960 |
C9—H9A | 0.980 | C24—H24B | 0.960 |
C10—C11 | 1.372 (4) | ||
C16—O3—C8 | 93.09 (16) | C13—C12—H12A | 119.8 |
C15—O4—C16 | 107.99 (19) | C11—C12—H12A | 119.8 |
C1—N1—C23 | 126.5 (2) | C12—C13—C14 | 121.5 (3) |
C1—N1—C2 | 109.43 (18) | C12—C13—H13A | 119.2 |
C23—N1—C2 | 124.0 (2) | C14—C13—H13A | 119.2 |
O2—C1—N1 | 126.2 (2) | C15—C14—C13 | 117.2 (3) |
O2—C1—C8 | 125.7 (2) | C15—C14—H14A | 121.4 |
N1—C1—C8 | 108.1 (2) | C13—C14—H14A | 121.4 |
C3—C2—C7 | 121.5 (2) | O4—C15—C14 | 124.2 (3) |
C3—C2—N1 | 128.8 (2) | O4—C15—C10 | 113.8 (2) |
C7—C2—N1 | 109.6 (2) | C14—C15—C10 | 121.9 (3) |
C2—C3—C4 | 117.2 (3) | O3—C16—O4 | 110.5 (2) |
C2—C3—H3A | 121.4 | O3—C16—C17 | 114.3 (2) |
C4—C3—H3A | 121.4 | O4—C16—C17 | 109.1 (2) |
C5—C4—C3 | 121.9 (3) | O3—C16—C9 | 91.08 (17) |
C5—C4—H4A | 119.1 | O4—C16—C9 | 107.13 (19) |
C3—C4—H4A | 119.1 | C17—C16—C9 | 123.4 (2) |
C6—C5—C4 | 120.3 (3) | C18—C17—C22 | 118.5 (3) |
C6—C5—H5A | 119.8 | C18—C17—C16 | 120.3 (2) |
C4—C5—H5A | 119.8 | C22—C17—C16 | 121.2 (2) |
C5—C6—C7 | 119.0 (3) | C19—C18—C17 | 120.4 (3) |
C5—C6—H6A | 120.5 | C19—C18—H18A | 119.8 |
C7—C6—H6A | 120.5 | C17—C18—H18A | 119.8 |
C6—C7—C2 | 120.0 (2) | C20—C19—C18 | 120.4 (3) |
C6—C7—C8 | 130.1 (2) | C20—C19—H19A | 119.8 |
C2—C7—C8 | 109.7 (2) | C18—C19—H19A | 119.8 |
O3—C8—C7 | 115.07 (19) | C21—C20—C19 | 119.6 (3) |
O3—C8—C1 | 110.00 (19) | C21—C20—H20A | 120.2 |
C7—C8—C1 | 102.86 (19) | C19—C20—H20A | 120.2 |
O3—C8—C9 | 90.29 (16) | C20—C21—C22 | 120.5 (3) |
C7—C8—C9 | 124.6 (2) | C20—C21—H21A | 119.7 |
C1—C8—C9 | 113.71 (19) | C22—C21—H21A | 119.7 |
C10—C9—C8 | 117.0 (2) | C21—C22—C17 | 120.4 (3) |
C10—C9—C16 | 103.13 (19) | C21—C22—H22A | 119.8 |
C8—C9—C16 | 85.28 (17) | C17—C22—H22A | 119.8 |
C10—C9—H9A | 115.6 | O1—C23—N1 | 119.8 (3) |
C8—C9—H9A | 115.6 | O1—C23—C24 | 122.8 (2) |
C16—C9—H9A | 115.6 | N1—C23—C24 | 117.5 (2) |
C11—C10—C15 | 120.1 (2) | C23—C24—H24C | 109.5 |
C11—C10—C9 | 132.1 (2) | C23—C24—H24A | 109.5 |
C15—C10—C9 | 107.9 (2) | H24C—C24—H24A | 109.5 |
C10—C11—C12 | 118.9 (3) | C23—C24—H24B | 109.5 |
C10—C11—H11A | 120.5 | H24C—C24—H24B | 109.5 |
C12—C11—H11A | 120.5 | H24A—C24—H24B | 109.5 |
C13—C12—C11 | 120.4 (3) | ||
C23—N1—C1—O2 | −9.9 (4) | C15—C10—C11—C12 | 0.7 (4) |
C2—N1—C1—O2 | 173.5 (2) | C9—C10—C11—C12 | −179.7 (3) |
C23—N1—C1—C8 | 171.4 (2) | C10—C11—C12—C13 | −0.4 (4) |
C2—N1—C1—C8 | −5.2 (3) | C11—C12—C13—C14 | 0.3 (5) |
C1—N1—C2—C3 | −179.5 (2) | C12—C13—C14—C15 | −0.5 (5) |
C23—N1—C2—C3 | 3.8 (4) | C16—O4—C15—C14 | 179.9 (3) |
C1—N1—C2—C7 | 3.6 (3) | C16—O4—C15—C10 | 0.3 (3) |
C23—N1—C2—C7 | −173.0 (2) | C13—C14—C15—O4 | −178.7 (3) |
C7—C2—C3—C4 | 0.6 (4) | C13—C14—C15—C10 | 0.9 (4) |
N1—C2—C3—C4 | −175.8 (2) | C11—C10—C15—O4 | 178.6 (2) |
C2—C3—C4—C5 | 0.2 (4) | C9—C10—C15—O4 | −1.1 (3) |
C3—C4—C5—C6 | −0.4 (5) | C11—C10—C15—C14 | −1.0 (4) |
C4—C5—C6—C7 | −0.2 (4) | C9—C10—C15—C14 | 179.3 (2) |
C5—C6—C7—C2 | 1.0 (4) | C8—O3—C16—O4 | −112.7 (2) |
C5—C6—C7—C8 | 176.5 (3) | C8—O3—C16—C17 | 123.9 (2) |
C3—C2—C7—C6 | −1.3 (4) | C8—O3—C16—C9 | −3.93 (17) |
N1—C2—C7—C6 | 175.8 (2) | C15—O4—C16—O3 | 98.4 (2) |
C3—C2—C7—C8 | −177.6 (2) | C15—O4—C16—C17 | −135.2 (2) |
N1—C2—C7—C8 | −0.5 (3) | C15—O4—C16—C9 | 0.6 (2) |
C16—O3—C8—C7 | 132.9 (2) | C10—C9—C16—O3 | −112.98 (19) |
C16—O3—C8—C1 | −111.5 (2) | C8—C9—C16—O3 | 3.71 (16) |
C16—O3—C8—C9 | 3.94 (18) | C10—C9—C16—O4 | −1.2 (2) |
C6—C7—C8—O3 | −58.7 (4) | C8—C9—C16—O4 | 115.5 (2) |
C2—C7—C8—O3 | 117.2 (2) | C10—C9—C16—C17 | 126.7 (2) |
C6—C7—C8—C1 | −178.3 (3) | C8—C9—C16—C17 | −116.6 (2) |
C2—C7—C8—C1 | −2.5 (3) | O3—C16—C17—C18 | 159.5 (2) |
C6—C7—C8—C9 | 50.5 (4) | O4—C16—C17—C18 | 35.3 (3) |
C2—C7—C8—C9 | −133.6 (2) | C9—C16—C17—C18 | −91.7 (3) |
O2—C1—C8—O3 | 62.9 (3) | O3—C16—C17—C22 | −23.6 (3) |
N1—C1—C8—O3 | −118.4 (2) | O4—C16—C17—C22 | −147.8 (2) |
O2—C1—C8—C7 | −174.1 (3) | C9—C16—C17—C22 | 85.2 (3) |
N1—C1—C8—C7 | 4.6 (3) | C22—C17—C18—C19 | −1.8 (4) |
O2—C1—C8—C9 | −36.7 (4) | C16—C17—C18—C19 | 175.2 (3) |
N1—C1—C8—C9 | 142.0 (2) | C17—C18—C19—C20 | 0.4 (5) |
O3—C8—C9—C10 | 98.7 (2) | C18—C19—C20—C21 | 0.3 (5) |
C7—C8—C9—C10 | −22.5 (3) | C19—C20—C21—C22 | 0.5 (5) |
C1—C8—C9—C10 | −149.2 (2) | C20—C21—C22—C17 | −1.9 (4) |
O3—C8—C9—C16 | −3.65 (16) | C18—C17—C22—C21 | 2.6 (4) |
C7—C8—C9—C16 | −124.9 (2) | C16—C17—C22—C21 | −174.4 (2) |
C1—C8—C9—C16 | 108.4 (2) | C1—N1—C23—O1 | 170.4 (3) |
C8—C9—C10—C11 | 90.3 (3) | C2—N1—C23—O1 | −13.5 (4) |
C16—C9—C10—C11 | −178.3 (3) | C1—N1—C23—C24 | −9.9 (4) |
C8—C9—C10—C15 | −90.1 (3) | C2—N1—C23—C24 | 166.2 (2) |
C16—C9—C10—C15 | 1.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1 | 0.93 | 2.29 | 2.839 (4) | 117 |
C22—H22A···O3 | 0.93 | 2.53 | 2.857 (3) | 100 |
Experimental details
Crystal data | |
Chemical formula | C24H17NO4 |
Mr | 383.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.2136 (2), 10.2904 (3), 10.9603 (3) |
α, β, γ (°) | 68.119 (1), 80.830 (1), 75.083 (1) |
V (Å3) | 929.47 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.36 × 0.28 × 0.18 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5322, 3231, 2148 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.169, 0.94 |
No. of reflections | 3231 |
No. of parameters | 264 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.31 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
O3—C16 | 1.439 (3) | C2—C7 | 1.396 (3) |
O3—C8 | 1.462 (3) | C7—C8 | 1.495 (3) |
O4—C15 | 1.378 (3) | C8—C9 | 1.553 (3) |
O4—C16 | 1.442 (3) | C9—C10 | 1.493 (3) |
N1—C1 | 1.403 (3) | C9—C16 | 1.555 (3) |
N1—C2 | 1.437 (3) | C10—C15 | 1.391 (4) |
C1—C8 | 1.541 (3) | C16—C17 | 1.497 (4) |
C16—O3—C8 | 93.09 (16) | O3—C8—C9 | 90.29 (16) |
C15—O4—C16 | 107.99 (19) | O3—C16—C9 | 91.08 (17) |
C1—N1—C2 | 109.43 (18) | O4—C16—C9 | 107.13 (19) |
N1—C1—C8 | 108.1 (2) | C17—C16—C9 | 123.4 (2) |
C7—C8—C1 | 102.86 (19) | ||
C1—N1—C2—C3 | −179.5 (2) | C16—C9—C10—C11 | −178.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1 | 0.93 | 2.2913 | 2.839 (4) | 117 |
C22—H22A···O3 | 0.93 | 2.5318 | 2.857 (3) | 100 |
The photoinduced reactions of 1H-indole-2,3-dione (isatin) derivatives, which are compounds of interest mainly due to their biological activities (Bieck et al., 1993) and their widespread use as synthetic precursors of many natural and unnatural products (Popp, 1975; Shvekhgeimer, 1996), have been investigated intensively (Ling et al., 1998; Xue et al., 2000, 2001) in order to extend the scope of the photoinduced reactions of carbonyl compounds. The title compound, (I), was one of the two diastereomers obtained in the photoinduced reaction of 1-acetylisatin with 2-phenylbenzofuran. To confirm its conformation and stereochemistry an X-ray structure determination of (I) was undertaken.
The bond lengths and angles observed in the title compound show normal values (Allen et al., 1987). These values within the indole and oxetene moieties agree with those of the corresponding related structures previously studied (Zukerman-Schpector et al., 1992; Prakash et al., 1997). The oxetane ring shows a slight puckering and therefore deviates from planarity, with a maximum deviation of -0.025 (3) Å and a dihedral angle of 174.6 (3)° between the O3/C8/C16 and C8/C9/C16 planes. Non-planar oxetanes also are observed in other derivatives (Morris et al., 1987; Khan et al., 1991; Prakash et al., 1997). The benzofuran and indole moieties are almost planar and make dihedral angles of 65.5 (2) and 89.0 (2)° with the mean plane through the oxetane. This corresponds to the synclinal configuration for the two moieties with respect to the oxetane. The angle C9—C16—C17 is 123.4 (2)°, implying that the attached phenyl ring is pushed slightly away from the benzofuran and indole moieties, and it forms a dihedral angle of 68.0 (2)° with the oxetane ring. Atom O2 deviates by -0.092 (2) Å from the mean plane of the indole moiety, while the acetyl group attached at N1 is twisted by 13.9 (2)° from the plane. The O1 atom of the acetyl group and the O2 atom show weak intramolecular hydrogen-bond interactions (Table 2) forming closed rings O1—C23—N1—C2—C3—H3A and O3—C16—C17—C22—H22A. These interactions stabilize the molecular structure.