Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802006013/ci6111sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802006013/ci6111Isup2.hkl |
CCDC reference: 185779
The title compound was prepared by a photoinduced reaction of 1-acetylisatin with 1,4-diphenylbuta-1,4-diyne in benzene, and was isolated from the reaction mixtures by column chromatography on silica gel. Single crystals suitable for X-ray diffraction were grown by slow evaporation from a acetone–petroleum ether (2:1) mixture.
The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with aromatic C—H distances of 0.93 Å and methylene C—H distances of 0.96 Å.
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 title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. Packing of the title molecules, viewed down the b axis. |
C26H17NO3 | F(000) = 408 |
Mr = 391.41 | Dx = 1.311 Mg m−3 |
Triclinic, P1 | Melting point: 462(1)K K |
a = 8.5729 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3557 (4) Å | Cell parameters from 3782 reflections |
c = 13.7085 (6) Å | θ = 2.6–28.3° |
α = 107.284 (1)° | µ = 0.09 mm−1 |
β = 99.774 (1)° | T = 233 K |
γ = 102.644 (1)° | Needle, yellow |
V = 991.32 (8) Å3 | 0.44 × 0.20 × 0.14 mm |
Z = 2 |
Siemens SMART CCD area-detector diffractometer | 3529 independent reflections |
Radiation source: fine-focus sealed tube | 2673 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.5°, θmin = 2.6° |
ω scans | h = −10→10 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.963, Tmax = 0.988 | l = −16→15 |
9930 measured 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)] = 0.077 | H-atom parameters constrained |
wR(F2) = 0.210 | w = 1/[σ2(Fo2) + (0.1552P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
3529 reflections | Δρmax = 0.35 e Å−3 |
273 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.12 (2) |
C26H17NO3 | γ = 102.644 (1)° |
Mr = 391.41 | V = 991.32 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5729 (4) Å | Mo Kα radiation |
b = 9.3557 (4) Å | µ = 0.09 mm−1 |
c = 13.7085 (6) Å | T = 233 K |
α = 107.284 (1)° | 0.44 × 0.20 × 0.14 mm |
β = 99.774 (1)° |
Siemens SMART CCD area-detector diffractometer | 3529 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 2673 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.988 | Rint = 0.068 |
9930 measured reflections |
R[F2 > 2σ(F2)] = 0.077 | 0 restraints |
wR(F2) = 0.210 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.35 e Å−3 |
3529 reflections | Δρmin = −0.37 e Å−3 |
273 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 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 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 | ||
N1 | 0.6265 (2) | 0.1992 (2) | 0.04026 (14) | 0.0375 (5) | |
O1 | 0.4220 (2) | 0.3275 (2) | 0.05543 (14) | 0.0548 (5) | |
O2 | 0.7558 (3) | 0.1425 (3) | −0.08983 (15) | 0.0908 (9) | |
O3 | 0.6362 (2) | 0.4301 (2) | 0.44930 (13) | 0.0568 (5) | |
C1 | 0.5184 (3) | 0.2707 (2) | 0.09268 (17) | 0.0360 (5) | |
C2 | 0.7232 (3) | 0.1469 (2) | 0.11006 (17) | 0.0375 (5) | |
C3 | 0.8388 (3) | 0.0668 (3) | 0.0918 (2) | 0.0502 (6) | |
H3 | 0.8627 | 0.0380 | 0.0263 | 0.060* | |
C4 | 0.9181 (4) | 0.0307 (3) | 0.1744 (2) | 0.0600 (7) | |
H4 | 0.9966 | −0.0231 | 0.1639 | 0.072* | |
C5 | 0.8831 (3) | 0.0728 (4) | 0.2711 (2) | 0.0590 (7) | |
H5 | 0.9393 | 0.0485 | 0.3254 | 0.071* | |
C6 | 0.7656 (3) | 0.1507 (3) | 0.2889 (2) | 0.0499 (6) | |
H6 | 0.7412 | 0.1779 | 0.3543 | 0.060* | |
C7 | 0.6848 (3) | 0.1877 (2) | 0.20741 (17) | 0.0352 (5) | |
C8 | 0.5551 (3) | 0.2645 (2) | 0.20088 (16) | 0.0340 (5) | |
C9 | 0.4742 (3) | 0.3200 (2) | 0.27330 (17) | 0.0358 (5) | |
C10 | 0.5229 (3) | 0.3243 (2) | 0.38685 (16) | 0.0365 (5) | |
C11 | 0.4229 (3) | 0.2003 (2) | 0.41530 (16) | 0.0352 (5) | |
C12 | 0.3192 (3) | 0.0643 (3) | 0.33816 (17) | 0.0402 (5) | |
H12 | 0.3090 | 0.0519 | 0.2673 | 0.048* | |
C13 | 0.2310 (3) | −0.0526 (3) | 0.36567 (19) | 0.0492 (6) | |
H13 | 0.1640 | −0.1452 | 0.3137 | 0.059* | |
C14 | 0.2427 (4) | −0.0318 (3) | 0.4709 (2) | 0.0554 (7) | |
H14 | 0.1806 | −0.1095 | 0.4895 | 0.066* | |
C15 | 0.3446 (3) | 0.1020 (3) | 0.5479 (2) | 0.0547 (7) | |
H15 | 0.3517 | 0.1145 | 0.6185 | 0.066* | |
C16 | 0.4369 (3) | 0.2186 (3) | 0.52146 (18) | 0.0478 (6) | |
H16 | 0.5079 | 0.3087 | 0.5740 | 0.057* | |
C17 | 0.3417 (3) | 0.3830 (3) | 0.25509 (18) | 0.0398 (5) | |
C18 | 0.2260 (3) | 0.4358 (3) | 0.25216 (19) | 0.0425 (6) | |
C19 | 0.0901 (3) | 0.4988 (3) | 0.24792 (19) | 0.0424 (6) | |
C20 | 0.0166 (3) | 0.5209 (3) | 0.1569 (2) | 0.0558 (7) | |
H20 | 0.0564 | 0.4932 | 0.0970 | 0.067* | |
C21 | −0.1139 (4) | 0.5832 (4) | 0.1551 (3) | 0.0680 (9) | |
H21 | −0.1609 | 0.5995 | 0.0945 | 0.082* | |
C22 | −0.1755 (3) | 0.6215 (3) | 0.2421 (3) | 0.0676 (9) | |
H22 | −0.2655 | 0.6619 | 0.2399 | 0.081* | |
C23 | −0.1055 (3) | 0.6009 (3) | 0.3322 (3) | 0.0622 (8) | |
H23 | −0.1470 | 0.6287 | 0.3914 | 0.075* | |
C24 | 0.0255 (3) | 0.5397 (3) | 0.3359 (2) | 0.0495 (6) | |
H24 | 0.0719 | 0.5252 | 0.3974 | 0.059* | |
C25 | 0.6486 (3) | 0.1953 (3) | −0.05876 (17) | 0.0492 (6) | |
C26 | 0.5448 (4) | 0.2588 (4) | −0.1222 (2) | 0.0649 (8) | |
H26A | 0.4306 | 0.2043 | −0.1346 | 0.097* | |
H26B | 0.5730 | 0.2453 | −0.1886 | 0.097* | |
H26C | 0.5633 | 0.3680 | −0.0849 | 0.097* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0396 (10) | 0.0414 (10) | 0.0352 (10) | 0.0171 (8) | 0.0098 (8) | 0.0144 (8) |
O1 | 0.0601 (11) | 0.0714 (12) | 0.0516 (10) | 0.0400 (9) | 0.0152 (9) | 0.0322 (9) |
O2 | 0.1123 (19) | 0.147 (2) | 0.0458 (12) | 0.0874 (19) | 0.0362 (13) | 0.0353 (13) |
O3 | 0.0540 (11) | 0.0565 (11) | 0.0449 (10) | −0.0022 (9) | 0.0087 (8) | 0.0116 (8) |
C1 | 0.0363 (11) | 0.0364 (11) | 0.0388 (12) | 0.0150 (9) | 0.0086 (9) | 0.0152 (9) |
C2 | 0.0354 (11) | 0.0371 (11) | 0.0420 (12) | 0.0132 (9) | 0.0089 (9) | 0.0150 (9) |
C3 | 0.0523 (15) | 0.0594 (15) | 0.0518 (14) | 0.0317 (12) | 0.0226 (12) | 0.0208 (12) |
C4 | 0.0568 (16) | 0.0703 (18) | 0.0757 (19) | 0.0415 (14) | 0.0252 (14) | 0.0363 (15) |
C5 | 0.0553 (16) | 0.0818 (19) | 0.0653 (17) | 0.0402 (14) | 0.0184 (14) | 0.0450 (15) |
C6 | 0.0538 (15) | 0.0649 (16) | 0.0490 (14) | 0.0317 (12) | 0.0175 (12) | 0.0325 (12) |
C7 | 0.0318 (11) | 0.0356 (11) | 0.0423 (12) | 0.0127 (8) | 0.0098 (9) | 0.0166 (9) |
C8 | 0.0354 (11) | 0.0324 (10) | 0.0370 (11) | 0.0118 (8) | 0.0095 (9) | 0.0144 (9) |
C9 | 0.0365 (12) | 0.0324 (11) | 0.0400 (12) | 0.0103 (9) | 0.0096 (9) | 0.0144 (9) |
C10 | 0.0350 (11) | 0.0393 (12) | 0.0369 (11) | 0.0162 (9) | 0.0121 (9) | 0.0101 (9) |
C11 | 0.0386 (12) | 0.0368 (11) | 0.0337 (11) | 0.0167 (9) | 0.0095 (9) | 0.0127 (9) |
C12 | 0.0432 (13) | 0.0431 (12) | 0.0344 (11) | 0.0123 (10) | 0.0068 (9) | 0.0153 (9) |
C13 | 0.0512 (15) | 0.0436 (13) | 0.0472 (14) | 0.0075 (11) | 0.0039 (11) | 0.0172 (11) |
C14 | 0.0665 (17) | 0.0514 (15) | 0.0535 (15) | 0.0131 (13) | 0.0140 (13) | 0.0290 (12) |
C15 | 0.0717 (18) | 0.0594 (16) | 0.0406 (13) | 0.0195 (13) | 0.0190 (12) | 0.0249 (12) |
C16 | 0.0638 (16) | 0.0408 (13) | 0.0351 (12) | 0.0145 (11) | 0.0105 (11) | 0.0093 (10) |
C17 | 0.0394 (12) | 0.0412 (12) | 0.0415 (12) | 0.0153 (10) | 0.0114 (10) | 0.0150 (10) |
C18 | 0.0404 (13) | 0.0411 (12) | 0.0475 (13) | 0.0139 (10) | 0.0116 (10) | 0.0156 (10) |
C19 | 0.0372 (12) | 0.0360 (11) | 0.0544 (14) | 0.0128 (9) | 0.0124 (10) | 0.0141 (10) |
C20 | 0.0586 (16) | 0.0556 (15) | 0.0517 (15) | 0.0204 (13) | 0.0059 (12) | 0.0182 (12) |
C21 | 0.0615 (18) | 0.0611 (17) | 0.074 (2) | 0.0249 (14) | −0.0070 (16) | 0.0215 (15) |
C22 | 0.0413 (15) | 0.0561 (17) | 0.106 (3) | 0.0233 (12) | 0.0130 (16) | 0.0256 (16) |
C23 | 0.0528 (16) | 0.0522 (15) | 0.091 (2) | 0.0198 (12) | 0.0365 (16) | 0.0241 (15) |
C24 | 0.0471 (14) | 0.0467 (13) | 0.0632 (16) | 0.0156 (11) | 0.0224 (12) | 0.0251 (12) |
C25 | 0.0562 (15) | 0.0585 (15) | 0.0305 (11) | 0.0208 (12) | 0.0093 (11) | 0.0096 (11) |
C26 | 0.083 (2) | 0.081 (2) | 0.0418 (14) | 0.0350 (17) | 0.0153 (14) | 0.0287 (14) |
N1—C25 | 1.393 (3) | C12—H12 | 0.93 |
N1—C2 | 1.425 (3) | C13—C14 | 1.379 (4) |
N1—C1 | 1.426 (3) | C13—H13 | 0.93 |
O1—C1 | 1.198 (3) | C14—C15 | 1.366 (4) |
O2—C25 | 1.216 (3) | C14—H14 | 0.93 |
O3—C10 | 1.204 (3) | C15—C16 | 1.379 (3) |
C1—C8 | 1.484 (3) | C15—H15 | 0.93 |
C2—C3 | 1.380 (3) | C16—H16 | 0.93 |
C2—C7 | 1.392 (3) | C17—C18 | 1.201 (3) |
C3—C4 | 1.387 (4) | C18—C19 | 1.416 (3) |
C3—H3 | 0.93 | C19—C20 | 1.392 (4) |
C4—C5 | 1.372 (4) | C19—C24 | 1.397 (3) |
C4—H4 | 0.93 | C20—C21 | 1.370 (4) |
C5—C6 | 1.380 (4) | C20—H20 | 0.93 |
C5—H5 | 0.93 | C21—C22 | 1.368 (5) |
C6—C7 | 1.386 (3) | C21—H21 | 0.93 |
C6—H6 | 0.93 | C22—C23 | 1.365 (5) |
C7—C8 | 1.454 (3) | C22—H22 | 0.93 |
C8—C9 | 1.350 (3) | C23—C24 | 1.368 (4) |
C9—C17 | 1.409 (3) | C23—H23 | 0.93 |
C9—C10 | 1.528 (3) | C24—H24 | 0.93 |
C10—C11 | 1.477 (3) | C25—C26 | 1.475 (4) |
C11—C12 | 1.383 (3) | C26—H26A | 0.96 |
C11—C16 | 1.395 (3) | C26—H26B | 0.96 |
C12—C13 | 1.375 (3) | C26—H26C | 0.96 |
C25—N1—C2 | 124.5 (2) | C12—C13—H13 | 120.2 |
C25—N1—C1 | 126.08 (19) | C14—C13—H13 | 120.2 |
C2—N1—C1 | 109.10 (17) | C15—C14—C13 | 120.6 (2) |
O1—C1—N1 | 125.4 (2) | C15—C14—H14 | 119.7 |
O1—C1—C8 | 128.3 (2) | C13—C14—H14 | 119.7 |
N1—C1—C8 | 106.18 (17) | C14—C15—C16 | 120.4 (2) |
C3—C2—C7 | 121.2 (2) | C14—C15—H15 | 119.8 |
C3—C2—N1 | 129.2 (2) | C16—C15—H15 | 119.8 |
C7—C2—N1 | 109.57 (19) | C15—C16—C11 | 119.4 (2) |
C2—C3—C4 | 117.9 (2) | C15—C16—H16 | 120.3 |
C2—C3—H3 | 121.1 | C11—C16—H16 | 120.3 |
C4—C3—H3 | 121.1 | C18—C17—C9 | 171.4 (2) |
C5—C4—C3 | 121.3 (2) | C17—C18—C19 | 179.4 (3) |
C5—C4—H4 | 119.4 | C20—C19—C24 | 118.2 (2) |
C3—C4—H4 | 119.4 | C20—C19—C18 | 121.5 (2) |
C4—C5—C6 | 120.9 (2) | C24—C19—C18 | 120.3 (2) |
C4—C5—H5 | 119.6 | C21—C20—C19 | 120.4 (3) |
C6—C5—H5 | 119.6 | C21—C20—H20 | 119.8 |
C5—C6—C7 | 118.7 (2) | C19—C20—H20 | 119.8 |
C5—C6—H6 | 120.6 | C22—C21—C20 | 120.3 (3) |
C7—C6—H6 | 120.6 | C22—C21—H21 | 119.8 |
C6—C7—C2 | 120.0 (2) | C20—C21—H21 | 119.8 |
C6—C7—C8 | 131.6 (2) | C23—C22—C21 | 120.4 (3) |
C2—C7—C8 | 108.36 (18) | C23—C22—H22 | 119.8 |
C9—C8—C7 | 130.3 (2) | C21—C22—H22 | 119.8 |
C9—C8—C1 | 122.9 (2) | C22—C23—C24 | 120.3 (3) |
C7—C8—C1 | 106.74 (17) | C22—C23—H23 | 119.9 |
C8—C9—C17 | 125.1 (2) | C24—C23—H23 | 119.9 |
C8—C9—C10 | 122.07 (19) | C23—C24—C19 | 120.5 (3) |
C17—C9—C10 | 112.85 (18) | C23—C24—H24 | 119.8 |
O3—C10—C11 | 123.2 (2) | C19—C24—H24 | 119.8 |
O3—C10—C9 | 119.1 (2) | O2—C25—N1 | 119.0 (2) |
C11—C10—C9 | 117.65 (18) | O2—C25—C26 | 121.5 (2) |
C12—C11—C16 | 119.6 (2) | N1—C25—C26 | 119.5 (2) |
C12—C11—C10 | 120.90 (18) | C25—C26—H26A | 109.5 |
C16—C11—C10 | 119.5 (2) | C25—C26—H26B | 109.5 |
C13—C12—C11 | 120.4 (2) | H26A—C26—H26B | 109.5 |
C13—C12—H12 | 119.8 | C25—C26—H26C | 109.5 |
C11—C12—H12 | 119.8 | H26A—C26—H26C | 109.5 |
C12—C13—C14 | 119.6 (2) | H26B—C26—H26C | 109.5 |
C25—N1—C1—O1 | 5.9 (4) | C1—C8—C9—C10 | −175.06 (19) |
C2—N1—C1—O1 | 179.5 (2) | C8—C9—C10—O3 | 81.6 (3) |
C25—N1—C1—C8 | −172.1 (2) | C17—C9—C10—O3 | −96.9 (2) |
C2—N1—C1—C8 | 1.4 (2) | C8—C9—C10—C11 | −100.9 (2) |
C25—N1—C2—C3 | −8.9 (4) | C17—C9—C10—C11 | 80.7 (2) |
C1—N1—C2—C3 | 177.4 (2) | O3—C10—C11—C12 | −165.7 (2) |
C25—N1—C2—C7 | 171.5 (2) | C9—C10—C11—C12 | 16.9 (3) |
C1—N1—C2—C7 | −2.2 (2) | O3—C10—C11—C16 | 12.4 (3) |
C7—C2—C3—C4 | −1.2 (4) | C9—C10—C11—C16 | −165.1 (2) |
N1—C2—C3—C4 | 179.3 (2) | C16—C11—C12—C13 | −0.4 (3) |
C2—C3—C4—C5 | 0.1 (4) | C10—C11—C12—C13 | 177.7 (2) |
C3—C4—C5—C6 | 0.9 (5) | C11—C12—C13—C14 | 1.9 (4) |
C4—C5—C6—C7 | −0.8 (4) | C12—C13—C14—C15 | −1.9 (4) |
C5—C6—C7—C2 | −0.3 (4) | C13—C14—C15—C16 | 0.3 (4) |
C5—C6—C7—C8 | 178.4 (2) | C14—C15—C16—C11 | 1.3 (4) |
C3—C2—C7—C6 | 1.3 (3) | C12—C11—C16—C15 | −1.3 (4) |
N1—C2—C7—C6 | −179.1 (2) | C10—C11—C16—C15 | −179.4 (2) |
C3—C2—C7—C8 | −177.6 (2) | C24—C19—C20—C21 | 0.9 (4) |
N1—C2—C7—C8 | 2.0 (2) | C18—C19—C20—C21 | −179.5 (2) |
C6—C7—C8—C9 | −1.1 (4) | C19—C20—C21—C22 | −1.3 (4) |
C2—C7—C8—C9 | 177.7 (2) | C20—C21—C22—C23 | 1.3 (5) |
C6—C7—C8—C1 | −179.8 (2) | C21—C22—C23—C24 | −0.9 (4) |
C2—C7—C8—C1 | −1.1 (2) | C22—C23—C24—C19 | 0.5 (4) |
O1—C1—C8—C9 | 2.9 (4) | C20—C19—C24—C23 | −0.5 (4) |
N1—C1—C8—C9 | −179.10 (19) | C18—C19—C24—C23 | 179.8 (2) |
O1—C1—C8—C7 | −178.2 (2) | C2—N1—C25—O2 | 0.9 (4) |
N1—C1—C8—C7 | −0.2 (2) | C1—N1—C25—O2 | 173.4 (2) |
C7—C8—C9—C17 | −175.3 (2) | C2—N1—C25—C26 | −177.6 (2) |
C1—C8—C9—C17 | 3.2 (3) | C1—N1—C25—C26 | −5.0 (4) |
C7—C8—C9—C10 | 6.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2 | 0.93 | 2.27 | 2.806 (3) | 116 |
C12—H12···O2i | 0.93 | 2.45 | 3.247 (3) | 144 |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C26H17NO3 |
Mr | 391.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 233 |
a, b, c (Å) | 8.5729 (4), 9.3557 (4), 13.7085 (6) |
α, β, γ (°) | 107.284 (1), 99.774 (1), 102.644 (1) |
V (Å3) | 991.32 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.44 × 0.20 × 0.14 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.963, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9930, 3529, 2673 |
Rint | 0.068 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.077, 0.210, 0.99 |
No. of reflections | 3529 |
No. of parameters | 273 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.37 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
N1—C25 | 1.393 (3) | C8—C9 | 1.350 (3) |
N1—C2 | 1.425 (3) | C9—C17 | 1.409 (3) |
N1—C1 | 1.426 (3) | C9—C10 | 1.528 (3) |
O1—C1 | 1.198 (3) | C10—C11 | 1.477 (3) |
O2—C25 | 1.216 (3) | C17—C18 | 1.201 (3) |
O3—C10 | 1.204 (3) | C18—C19 | 1.416 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O2 | 0.93 | 2.27 | 2.806 (3) | 116 |
C12—H12···O2i | 0.93 | 2.45 | 3.247 (3) | 144 |
Symmetry code: (i) −x+1, −y, −z. |
The photoinduced reactions of 3H-indole-1,2-dione (isatin) with phenylacetylene and 1,2-diphenylacetylene have been investigated in our laboratory (Xue et al., 2000). In a continuation of these investigations, we have studied the photoinduced reactions of 1-acetylisatin with an excess of diphenylbuta-1,4-diyne in benzene. The title compound, (I), one of the isomers resulting from the above reaction, was isolated by column chromatography. The crystal structure analysis of the title compound was undertaken to elucidate the molecular conformation.
In (I), the bond lengths and angles within the benzoyl and phenylethynyl substituents agree with the corresponding values observed for the structure of 4-[α-benzoyl-α-(phenylethynyl)methylene]isoquinoline-1,3-dione (Usman et al., 2001). The increase in the C9—C10 bond distance [1.528 (3) Å] may be due to the steric effect of the bulky substitutents at C9.
The indole moiety is planar, with the atom N1 deviating a maximum of 0.026 (2) Å. The phenylethynyl and indole moieties are almost coplanar, with a dihedral angle of 6.0 (1)°. This facilitated the π-conjugation through the central C9 atom and resulted in a slight elongation of the C8—C9 and C17—C18 bonds and a shortening of the C9—C17 and C18—C19 bonds. The benzoyl phenyl ring is almost perpendicular to both the ethynyl phenyl ring and the indole moiety, with corresponding dihedral angles of 87.9 (1) and 85.7 (1)°, respectively.
In the title molecule, the acetyl O2 atom is invloved in an weak intramolecular C—H···O interaction (Table 2) which results in the formation a six-membered ring. The near coplanarity of the acetyl group with the indole plane [dihedral angle of 8.0 (1)°] may be due to this C—H···O interaction and the partial double-bond character of the N1—C25 bond. In the crystal, the molecules exist as C—H···O hydrogen-bonded dimers around inversion centres. The dimers translated along the a-cell direction are aligned so as to place the ethynylphenyl rings in close proximity to the five-membered rings (Fig. 2). The distance separating the ring centroids is calculated to be 3.550 (2) Å. The molecular packing is stabilized by these interactions along with the van der Waals interactions.