Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015350/cv6138sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015350/cv6138Isup2.hkl |
CCDC reference: 198332
Key indicators
- Single-crystal X-ray study
- T = 213 K
- Mean (C-C) = 0.003 Å
- R factor = 0.066
- wR factor = 0.155
- Data-to-parameter ratio = 17.3
checkCIF results
No syntax errors found Structure: I ------------ ADDSYM reports no extra symmetry
Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.794 RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.109
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The title compound was prepared by photoinduced oxygenation of 1,3-dibenzoyl-2-phenylindolizine in acetonitrile and was isolated by by column chromatography. Single crystals for X-ray measurement were obtained by slow evaporation of the solvent from a petroleum ether–ethyl acetate (5:1 v/v) solution.
The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); 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).
C28H19NO4 | Dx = 1.330 Mg m−3 |
Mr = 433.44 | Melting point: 416(1) K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1513 (4) Å | Cell parameters from 7367 reflections |
b = 9.7358 (3) Å | θ = 2.6–28.3° |
c = 16.9960 (5) Å | µ = 0.09 mm−1 |
β = 95.859 (1)° | T = 213 K |
V = 2164.8 (1) Å3 | Slab, colorless |
Z = 4 | 0.38 × 0.34 × 0.16 mm |
F(000) = 904 |
Siemens SMART CCD area-detector diffractometer | 2808 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.110 |
Graphite monochromator | θmax = 28.3°, θmin = 2.6° |
Detector resolution: 8.33 pixels mm-1 | h = −10→17 |
ω scans | k = −12→12 |
12406 measured reflections | l = −22→22 |
5164 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)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.156 | w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3 |
S = 0.79 | (Δ/σ)max = 0.001 |
5164 reflections | Δρmax = 0.34 e Å−3 |
299 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXTL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.021 (2) |
C28H19NO4 | V = 2164.8 (1) Å3 |
Mr = 433.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.1513 (4) Å | µ = 0.09 mm−1 |
b = 9.7358 (3) Å | T = 213 K |
c = 16.9960 (5) Å | 0.38 × 0.34 × 0.16 mm |
β = 95.859 (1)° |
Siemens SMART CCD area-detector diffractometer | 2808 reflections with I > 2σ(I) |
12406 measured reflections | Rint = 0.110 |
5164 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 0.79 | Δρmax = 0.34 e Å−3 |
5164 reflections | Δρmin = −0.28 e Å−3 |
299 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 | 0.83526 (14) | 0.90749 (16) | 0.20400 (11) | 0.0486 (5) | |
O2 | 0.92115 (12) | 0.66777 (17) | 0.33075 (9) | 0.0361 (4) | |
O3 | 0.67590 (11) | 0.71080 (14) | 0.22032 (8) | 0.0264 (4) | |
O4 | 0.49983 (11) | 0.61336 (17) | 0.27233 (10) | 0.0392 (4) | |
N1 | 0.81182 (13) | 0.49306 (18) | 0.19663 (10) | 0.0263 (4) | |
C1 | 0.9665 (2) | 0.8357 (3) | 0.09045 (15) | 0.0440 (7) | |
H1 | 0.9237 | 0.9109 | 0.0797 | 0.053* | |
C2 | 1.0363 (2) | 0.7997 (3) | 0.03841 (17) | 0.0566 (8) | |
H2 | 1.0387 | 0.8487 | −0.0083 | 0.068* | |
C3 | 1.1024 (2) | 0.6912 (3) | 0.05578 (16) | 0.0486 (7) | |
H3 | 1.1501 | 0.6685 | 0.0211 | 0.058* | |
C4 | 1.09795 (19) | 0.6166 (3) | 0.12394 (14) | 0.0404 (6) | |
H4 | 1.1428 | 0.5438 | 0.1355 | 0.048* | |
C5 | 1.02657 (17) | 0.6497 (2) | 0.17546 (13) | 0.0316 (5) | |
H5 | 1.0230 | 0.5983 | 0.2212 | 0.038* | |
C6 | 0.96051 (16) | 0.7591 (2) | 0.15902 (12) | 0.0275 (5) | |
C7 | 0.88147 (17) | 0.7990 (2) | 0.21090 (13) | 0.0294 (5) | |
C8 | 0.85547 (17) | 0.7092 (2) | 0.28065 (12) | 0.0249 (5) | |
C9 | 0.74207 (15) | 0.7085 (2) | 0.29277 (11) | 0.0210 (4) | |
C10 | 0.71388 (16) | 0.7979 (2) | 0.35897 (12) | 0.0239 (5) | |
C11 | 0.76665 (17) | 0.7884 (2) | 0.43381 (12) | 0.0304 (5) | |
H11 | 0.8193 | 0.7249 | 0.4434 | 0.037* | |
C12 | 0.7411 (2) | 0.8733 (2) | 0.49448 (14) | 0.0377 (6) | |
H12 | 0.7761 | 0.8652 | 0.5447 | 0.045* | |
C13 | 0.6650 (2) | 0.9688 (3) | 0.48098 (15) | 0.0437 (7) | |
H13 | 0.6489 | 1.0260 | 0.5218 | 0.052* | |
C14 | 0.6119 (2) | 0.9804 (3) | 0.40648 (16) | 0.0464 (7) | |
H14 | 0.5600 | 1.0450 | 0.3974 | 0.056* | |
C15 | 0.63636 (18) | 0.8950 (2) | 0.34505 (14) | 0.0361 (6) | |
H15 | 0.6010 | 0.9029 | 0.2950 | 0.043* | |
C16 | 0.67753 (15) | 0.5858 (2) | 0.26576 (12) | 0.0216 (4) | |
C17 | 0.72551 (15) | 0.4641 (2) | 0.22897 (11) | 0.0220 (4) | |
C18 | 0.85871 (17) | 0.3884 (2) | 0.16420 (13) | 0.0306 (5) | |
H18 | 0.9178 | 0.4070 | 0.1403 | 0.037* | |
C19 | 0.82440 (17) | 0.2545 (2) | 0.16420 (13) | 0.0324 (5) | |
H19 | 0.8609 | 0.1845 | 0.1427 | 0.039* | |
C20 | 0.73523 (18) | 0.2268 (2) | 0.19662 (13) | 0.0339 (5) | |
H20 | 0.7098 | 0.1377 | 0.1968 | 0.041* | |
C21 | 0.68369 (17) | 0.3330 (2) | 0.22905 (12) | 0.0281 (5) | |
H21 | 0.6224 | 0.3171 | 0.2504 | 0.034* | |
C22 | 0.57872 (15) | 0.5610 (2) | 0.30276 (12) | 0.0243 (5) | |
C23 | 0.57974 (16) | 0.4714 (2) | 0.37314 (12) | 0.0254 (5) | |
C24 | 0.66999 (18) | 0.4470 (2) | 0.42211 (13) | 0.0328 (5) | |
H24 | 0.7316 | 0.4828 | 0.4090 | 0.039* | |
C25 | 0.6673 (2) | 0.3698 (3) | 0.48981 (14) | 0.0454 (7) | |
H25 | 0.7271 | 0.3555 | 0.5230 | 0.054* | |
C26 | 0.5767 (2) | 0.3136 (3) | 0.50886 (15) | 0.0474 (7) | |
H26 | 0.5755 | 0.2625 | 0.5550 | 0.057* | |
C27 | 0.4878 (2) | 0.3332 (3) | 0.45943 (16) | 0.0441 (7) | |
H27 | 0.4272 | 0.2924 | 0.4712 | 0.053* | |
C28 | 0.48887 (19) | 0.4135 (2) | 0.39230 (14) | 0.0364 (6) | |
H28 | 0.4286 | 0.4288 | 0.3599 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0510 (12) | 0.0288 (10) | 0.0709 (13) | 0.0073 (8) | 0.0296 (10) | 0.0055 (8) |
O2 | 0.0186 (8) | 0.0565 (11) | 0.0322 (9) | 0.0007 (7) | −0.0020 (7) | −0.0023 (8) |
O3 | 0.0256 (8) | 0.0261 (8) | 0.0261 (7) | 0.0029 (6) | −0.0042 (6) | 0.0033 (6) |
O4 | 0.0160 (8) | 0.0451 (10) | 0.0550 (11) | 0.0062 (7) | −0.0044 (8) | 0.0036 (8) |
N1 | 0.0194 (10) | 0.0310 (10) | 0.0288 (9) | 0.0010 (8) | 0.0047 (8) | −0.0033 (7) |
C1 | 0.0403 (15) | 0.0440 (15) | 0.0505 (15) | 0.0043 (12) | 0.0175 (13) | 0.0145 (12) |
C2 | 0.058 (2) | 0.064 (2) | 0.0530 (17) | 0.0033 (15) | 0.0274 (15) | 0.0168 (14) |
C3 | 0.0387 (16) | 0.0563 (18) | 0.0549 (17) | −0.0005 (13) | 0.0248 (14) | −0.0006 (13) |
C4 | 0.0277 (14) | 0.0475 (15) | 0.0474 (15) | 0.0056 (11) | 0.0101 (12) | 0.0001 (12) |
C5 | 0.0235 (12) | 0.0359 (13) | 0.0351 (12) | −0.0004 (10) | 0.0022 (10) | −0.0008 (10) |
C6 | 0.0213 (12) | 0.0287 (12) | 0.0328 (11) | −0.0063 (9) | 0.0036 (9) | −0.0025 (9) |
C7 | 0.0277 (13) | 0.0238 (12) | 0.0375 (12) | −0.0040 (9) | 0.0071 (10) | −0.0044 (9) |
C8 | 0.0228 (12) | 0.0240 (11) | 0.0281 (11) | −0.0008 (9) | 0.0033 (9) | −0.0054 (8) |
C9 | 0.0157 (10) | 0.0240 (11) | 0.0225 (10) | 0.0024 (8) | −0.0018 (8) | 0.0009 (8) |
C10 | 0.0214 (11) | 0.0215 (11) | 0.0293 (11) | −0.0020 (8) | 0.0054 (9) | −0.0009 (8) |
C11 | 0.0272 (13) | 0.0317 (12) | 0.0322 (12) | 0.0028 (9) | 0.0015 (10) | −0.0050 (9) |
C12 | 0.0430 (16) | 0.0394 (14) | 0.0311 (13) | −0.0055 (11) | 0.0049 (11) | −0.0093 (10) |
C13 | 0.0546 (18) | 0.0355 (14) | 0.0440 (15) | −0.0004 (12) | 0.0189 (13) | −0.0140 (11) |
C14 | 0.0450 (17) | 0.0384 (15) | 0.0569 (17) | 0.0167 (12) | 0.0109 (14) | −0.0090 (12) |
C15 | 0.0317 (14) | 0.0355 (13) | 0.0406 (13) | 0.0075 (10) | 0.0018 (11) | −0.0043 (10) |
C16 | 0.0157 (10) | 0.0233 (11) | 0.0250 (10) | 0.0029 (8) | −0.0021 (8) | 0.0001 (8) |
C17 | 0.0153 (10) | 0.0288 (11) | 0.0209 (10) | 0.0011 (8) | −0.0023 (8) | −0.0019 (8) |
C18 | 0.0220 (12) | 0.0392 (13) | 0.0315 (12) | 0.0021 (10) | 0.0064 (10) | −0.0068 (10) |
C19 | 0.0261 (13) | 0.0368 (13) | 0.0341 (12) | 0.0080 (10) | 0.0017 (10) | −0.0089 (10) |
C20 | 0.0336 (14) | 0.0280 (12) | 0.0396 (13) | −0.0014 (10) | 0.0016 (11) | −0.0078 (10) |
C21 | 0.0206 (12) | 0.0305 (12) | 0.0336 (12) | −0.0031 (9) | 0.0043 (9) | −0.0062 (9) |
C22 | 0.0132 (10) | 0.0268 (11) | 0.0319 (11) | 0.0010 (8) | −0.0033 (9) | −0.0064 (8) |
C23 | 0.0200 (11) | 0.0247 (11) | 0.0325 (12) | 0.0001 (9) | 0.0075 (9) | −0.0060 (9) |
C24 | 0.0260 (13) | 0.0385 (13) | 0.0346 (13) | 0.0053 (10) | 0.0058 (10) | 0.0022 (10) |
C25 | 0.0475 (17) | 0.0504 (16) | 0.0394 (14) | 0.0162 (13) | 0.0102 (13) | 0.0103 (12) |
C26 | 0.067 (2) | 0.0333 (14) | 0.0461 (15) | 0.0097 (13) | 0.0273 (15) | 0.0060 (11) |
C27 | 0.0478 (17) | 0.0324 (14) | 0.0572 (17) | −0.0095 (12) | 0.0297 (14) | −0.0076 (12) |
C28 | 0.0263 (13) | 0.0372 (14) | 0.0471 (14) | −0.0051 (10) | 0.0101 (11) | −0.0119 (11) |
O1—C7 | 1.218 (3) | C12—H12 | 0.9300 |
O2—C8 | 1.218 (3) | C13—C14 | 1.387 (4) |
O3—C9 | 1.434 (2) | C13—H13 | 0.9300 |
O3—C16 | 1.441 (2) | C14—C15 | 1.398 (3) |
O4—C22 | 1.222 (2) | C14—H14 | 0.9300 |
N1—C18 | 1.339 (3) | C15—H15 | 0.9300 |
N1—C17 | 1.341 (2) | C16—C17 | 1.507 (3) |
C1—C2 | 1.383 (3) | C16—C22 | 1.520 (3) |
C1—C6 | 1.393 (3) | C17—C21 | 1.390 (3) |
C1—H1 | 0.9300 | C18—C19 | 1.379 (3) |
C2—C3 | 1.381 (4) | C18—H18 | 0.9300 |
C2—H2 | 0.9300 | C19—C20 | 1.372 (3) |
C3—C4 | 1.374 (3) | C19—H19 | 0.9300 |
C3—H3 | 0.9300 | C20—C21 | 1.381 (3) |
C4—C5 | 1.386 (3) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—H21 | 0.9300 |
C5—C6 | 1.385 (3) | C22—C23 | 1.479 (3) |
C5—H5 | 0.9300 | C23—C28 | 1.390 (3) |
C6—C7 | 1.482 (3) | C23—C24 | 1.399 (3) |
C7—C8 | 1.539 (3) | C24—C25 | 1.378 (3) |
C8—C9 | 1.526 (3) | C24—H24 | 0.9300 |
C9—C10 | 1.499 (3) | C25—C26 | 1.379 (4) |
C9—C16 | 1.509 (3) | C25—H25 | 0.9300 |
C10—C11 | 1.389 (3) | C26—C27 | 1.382 (4) |
C10—C15 | 1.392 (3) | C26—H26 | 0.9300 |
C11—C12 | 1.389 (3) | C27—C28 | 1.385 (3) |
C11—H11 | 0.9300 | C27—H27 | 0.9300 |
C12—C13 | 1.368 (4) | C28—H28 | 0.9300 |
C9—O3—C16 | 63.36 (12) | C15—C14—H14 | 120.0 |
C18—N1—C17 | 116.97 (18) | C10—C15—C14 | 119.8 (2) |
C2—C1—C6 | 119.8 (2) | C10—C15—H15 | 120.1 |
C2—C1—H1 | 120.1 | C14—C15—H15 | 120.1 |
C6—C1—H1 | 120.1 | O3—C16—C17 | 115.18 (15) |
C3—C2—C1 | 120.1 (2) | O3—C16—C9 | 58.09 (12) |
C3—C2—H2 | 120.0 | C17—C16—C9 | 120.12 (17) |
C1—C2—H2 | 120.0 | O3—C16—C22 | 112.92 (16) |
C4—C3—C2 | 120.4 (2) | C17—C16—C22 | 117.30 (17) |
C4—C3—H3 | 119.8 | C9—C16—C22 | 118.55 (16) |
C2—C3—H3 | 119.8 | N1—C17—C21 | 123.03 (19) |
C3—C4—C5 | 120.0 (2) | N1—C17—C16 | 114.36 (18) |
C3—C4—H4 | 120.0 | C21—C17—C16 | 122.60 (18) |
C5—C4—H4 | 120.0 | N1—C18—C19 | 123.7 (2) |
C6—C5—C4 | 120.2 (2) | N1—C18—H18 | 118.1 |
C6—C5—H5 | 119.9 | C19—C18—H18 | 118.1 |
C4—C5—H5 | 119.9 | C20—C19—C18 | 118.6 (2) |
C5—C6—C1 | 119.6 (2) | C20—C19—H19 | 120.7 |
C5—C6—C7 | 123.0 (2) | C18—C19—H19 | 120.7 |
C1—C6—C7 | 117.4 (2) | C19—C20—C21 | 119.2 (2) |
O1—C7—C6 | 122.9 (2) | C19—C20—H20 | 120.4 |
O1—C7—C8 | 114.74 (19) | C21—C20—H20 | 120.4 |
C6—C7—C8 | 122.26 (19) | C20—C21—C17 | 118.5 (2) |
O2—C8—C9 | 122.47 (18) | C20—C21—H21 | 120.8 |
O2—C8—C7 | 121.9 (2) | C17—C21—H21 | 120.8 |
C9—C8—C7 | 113.81 (18) | O4—C22—C23 | 121.69 (19) |
O3—C9—C10 | 117.42 (16) | O4—C22—C16 | 118.90 (19) |
O3—C9—C16 | 58.55 (12) | C23—C22—C16 | 119.38 (17) |
C10—C9—C16 | 120.90 (17) | C28—C23—C24 | 119.3 (2) |
O3—C9—C8 | 113.57 (15) | C28—C23—C22 | 119.4 (2) |
C10—C9—C8 | 114.73 (17) | C24—C23—C22 | 121.21 (19) |
C16—C9—C8 | 119.33 (16) | C25—C24—C23 | 119.8 (2) |
C11—C10—C15 | 119.31 (19) | C25—C24—H24 | 120.1 |
C11—C10—C9 | 120.68 (18) | C23—C24—H24 | 120.1 |
C15—C10—C9 | 120.0 (2) | C24—C25—C26 | 120.6 (3) |
C10—C11—C12 | 120.3 (2) | C24—C25—H25 | 119.7 |
C10—C11—H11 | 119.9 | C26—C25—H25 | 119.7 |
C12—C11—H11 | 119.9 | C25—C26—C27 | 120.0 (2) |
C13—C12—C11 | 120.5 (2) | C25—C26—H26 | 120.0 |
C13—C12—H12 | 119.7 | C27—C26—H26 | 120.0 |
C11—C12—H12 | 119.7 | C26—C27—C28 | 120.0 (2) |
C12—C13—C14 | 120.0 (2) | C26—C27—H27 | 120.0 |
C12—C13—H13 | 120.0 | C28—C27—H27 | 120.0 |
C14—C13—H13 | 120.0 | C27—C28—C23 | 120.2 (2) |
C13—C14—C15 | 120.1 (2) | C27—C28—H28 | 119.9 |
C13—C14—H14 | 120.0 | C23—C28—H28 | 119.9 |
C6—C1—C2—C3 | −2.3 (4) | C10—C9—C16—O3 | 105.3 (2) |
C1—C2—C3—C4 | 1.3 (5) | C8—C9—C16—O3 | −101.19 (18) |
C2—C3—C4—C5 | 0.3 (4) | O3—C9—C16—C17 | 102.61 (18) |
C3—C4—C5—C6 | −0.9 (4) | C10—C9—C16—C17 | −152.14 (18) |
C4—C5—C6—C1 | −0.1 (4) | C8—C9—C16—C17 | 1.4 (3) |
C4—C5—C6—C7 | 179.1 (2) | O3—C9—C16—C22 | −100.58 (18) |
C2—C1—C6—C5 | 1.7 (4) | C10—C9—C16—C22 | 4.7 (3) |
C2—C1—C6—C7 | −177.6 (2) | C8—C9—C16—C22 | 158.24 (18) |
C5—C6—C7—O1 | 167.3 (2) | C18—N1—C17—C21 | −0.8 (3) |
C1—C6—C7—O1 | −13.4 (3) | C18—N1—C17—C16 | 178.94 (18) |
C5—C6—C7—C8 | −9.4 (3) | O3—C16—C17—N1 | 42.7 (2) |
C1—C6—C7—C8 | 169.8 (2) | C9—C16—C17—N1 | −23.6 (3) |
O1—C7—C8—O2 | −125.2 (2) | C22—C16—C17—N1 | 179.31 (17) |
C6—C7—C8—O2 | 51.8 (3) | O3—C16—C17—C21 | −137.6 (2) |
O1—C7—C8—C9 | 40.0 (3) | C9—C16—C17—C21 | 156.13 (19) |
C6—C7—C8—C9 | −143.0 (2) | C22—C16—C17—C21 | −1.0 (3) |
C16—O3—C9—C10 | −111.15 (19) | C17—N1—C18—C19 | −1.6 (3) |
C16—O3—C9—C8 | 111.08 (18) | N1—C18—C19—C20 | 2.4 (4) |
O2—C8—C9—O3 | −157.78 (19) | C18—C19—C20—C21 | −0.9 (3) |
C7—C8—C9—O3 | 37.1 (2) | C19—C20—C21—C17 | −1.3 (3) |
O2—C8—C9—C10 | 63.3 (3) | N1—C17—C21—C20 | 2.2 (3) |
C7—C8—C9—C10 | −101.9 (2) | C16—C17—C21—C20 | −177.50 (19) |
O2—C8—C9—C16 | −91.9 (2) | O3—C16—C22—O4 | 24.6 (3) |
C7—C8—C9—C16 | 103.0 (2) | C17—C16—C22—O4 | −113.0 (2) |
O3—C9—C10—C11 | 171.87 (17) | C9—C16—C22—O4 | 89.6 (2) |
C16—C9—C10—C11 | 103.9 (2) | O3—C16—C22—C23 | −157.05 (17) |
C8—C9—C10—C11 | −50.8 (2) | C17—C16—C22—C23 | 65.4 (2) |
O3—C9—C10—C15 | −10.3 (3) | C9—C16—C22—C23 | −92.1 (2) |
C16—C9—C10—C15 | −78.3 (3) | O4—C22—C23—C28 | 18.5 (3) |
C8—C9—C10—C15 | 127.0 (2) | C16—C22—C23—C28 | −159.85 (18) |
C15—C10—C11—C12 | 1.1 (3) | O4—C22—C23—C24 | −159.6 (2) |
C9—C10—C11—C12 | 178.9 (2) | C16—C22—C23—C24 | 22.0 (3) |
C10—C11—C12—C13 | −1.1 (4) | C28—C23—C24—C25 | −2.0 (3) |
C11—C12—C13—C14 | 0.7 (4) | C22—C23—C24—C25 | 176.1 (2) |
C12—C13—C14—C15 | −0.3 (4) | C23—C24—C25—C26 | 1.5 (4) |
C11—C10—C15—C14 | −0.7 (3) | C24—C25—C26—C27 | 0.7 (4) |
C9—C10—C15—C14 | −178.5 (2) | C25—C26—C27—C28 | −2.4 (4) |
C13—C14—C15—C10 | 0.3 (4) | C26—C27—C28—C23 | 1.9 (3) |
C9—O3—C16—C17 | −111.12 (19) | C24—C23—C28—C27 | 0.3 (3) |
C9—O3—C16—C22 | 110.36 (18) | C22—C23—C28—C27 | −177.82 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O2 | 0.93 | 2.50 | 3.109 (3) | 124 |
C11—H11···O2 | 0.93 | 2.51 | 3.050 (3) | 117 |
C21—H21···O4i | 0.93 | 2.56 | 3.223 (3) | 129 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C28H19NO4 |
Mr | 433.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 213 |
a, b, c (Å) | 13.1513 (4), 9.7358 (3), 16.9960 (5) |
β (°) | 95.859 (1) |
V (Å3) | 2164.8 (1) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.38 × 0.34 × 0.16 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12406, 5164, 2808 |
Rint | 0.110 |
(sin θ/λ)max (Å−1) | 0.666 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.156, 0.79 |
No. of reflections | 5164 |
No. of parameters | 299 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.34, −0.28 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 1996), SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
O3—C9 | 1.434 (2) | O3—C16 | 1.441 (2) |
O3—C9—C10 | 117.42 (16) | O3—C16—C17 | 115.18 (15) |
C10—C9—C16 | 120.90 (17) | C17—C16—C9 | 120.12 (17) |
O3—C9—C8 | 113.57 (15) | O3—C16—C22 | 112.92 (16) |
C10—C9—C8 | 114.73 (17) | C17—C16—C22 | 117.30 (17) |
C16—C9—C8 | 119.33 (16) | C9—C16—C22 | 118.55 (16) |
Photoinduced oxygenation reactions of indolizine derivatives have been investigated intensively in our previous study (Tian et al., 2001). In continuation of that work, we have isolated the title compound, (I), which was obtained from the photo-oxygenation reactions of 1,3-dibenzoyl-2-phenylindolizine. We report here an X-ray crystallographic analysis at 213 K of (I), which was undertaken to establish its conformation and stereochemistry.
The bond lengths and angles observed in (I) (Fig. 1) are within normal ranges (Allen et al., 1987). The values within the oxirane (O3/C9/C16) agree with those of a related structure studied previously (Krishnakumar et al., 2002), except for a slight elongation of the C9—C16 bond [1.509 (3) Å versus 1.488 (4) Å (Krishnakumar et al., 2002)] due to the bulky substituents attached at atoms C9 and C16. The configurations of the substituents are conditioned by these two Csp3 atoms. Except for the bond angles within the oxirane, the average bond angles subtended at atoms C9 and C16 are 117.2 and 116.8°, respectively, while the two atoms are eclipsed, as determined by the torsion angles C8—C9—C16—C17 = 1.4 (3)° and C10—C9—C16—C22 = 4.7 (3)°.
In the dioxophenylethylene moiety (O1/O2/C1–C9), the two carbonyl groups form O1/C6/C7/C8 and O2/C7/C8/C9 planes. These two planes are twisted out of the phenyl ring by 11.7 (1) and 38.8 (1)°, respectively. The O2/C7/C8/C9 plane and the C10–C15 phenyl ring attached at atom C9 form dihedral angles of 56.1 (1) and 63.6 (2)°, respectivley, with the oxirane ring plane.
The pyridine ring (N1/C17–C21) attached at atom C16 is perpendicular to the oxirane ring plane, with a dihedral angle of 88.6 (2)°. The carbonyl group of the benzoyl moiety (O4/C22–C28) attached at the same atom is twisted from its aromatic ring by an angle of 20.8 (1)° and the O4/C16/C22/C23 plane makes a dihedral angle of 61.8 (2)° with the oxirane ring plane.
In the packing, the molecules are interconnected by C21—H21···O4i interactions [H21···O4i 2.56 Å and C21—H21···O4i 129°; symmetry code: (i) 1 − x, y − 1/2, 1/2 − z] into zig-ag molecular chains along the b direction (Fig. 2). These interactions, along with the dipole–dipole and van der Waals interactions, stabilize the packing.