Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008857/cv6186sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008857/cv6186Isup2.hkl |
CCDC reference: 214640
The title compound was separated by column chromatography on silica gel with petroleum ether–ethyl acetate as eluants. Single crystals suitable for X-ray diffraction measurement were obtained from slow evaporation of a petroleum ether–acetone solution.
All H atoms were located from difference Fourier maps and refined isotropically [C—H = 0.92 (2)–1.02 (2) Å]. Owing to large fraction of weak data at higher angles, the 2θ maximum was limited to 52°. The maximum and minimum electron-density peaks are located 0.98 Å from O3 and 1.29 Å from C6, respectively.
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, 2003).
Fig. 1. The structure of the compound (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. |
C29H19NO3 | F(000) = 448 |
Mr = 429.45 | Dx = 1.324 Mg m−3 |
Triclinic, P1 | Melting point: 466(1) K |
a = 8.3475 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.8671 (6) Å | Cell parameters from 4070 reflections |
c = 11.9106 (6) Å | θ = 2.6–28.3° |
α = 74.148 (1)° | µ = 0.09 mm−1 |
β = 89.736 (1)° | T = 293 K |
γ = 72.344 (1)° | Block, yellow |
V = 1077.59 (9) Å3 | 0.50 × 0.40 × 0.30 mm |
Z = 2 |
Siemens SMART CCD area-detector diffractometer | 3482 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 26.0°, θmin = 2.6° |
Detector resolution: 8.33 pixels mm-1 | h = −10→7 |
ω scans | k = −14→14 |
5771 measured reflections | l = −13→14 |
4110 independent reflections |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.1949P] where P = (Fo2 + 2Fc2)/3 |
4110 reflections | (Δ/σ)max < 0.001 |
374 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C29H19NO3 | γ = 72.344 (1)° |
Mr = 429.45 | V = 1077.59 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.3475 (4) Å | Mo Kα radiation |
b = 11.8671 (6) Å | µ = 0.09 mm−1 |
c = 11.9106 (6) Å | T = 293 K |
α = 74.148 (1)° | 0.50 × 0.40 × 0.30 mm |
β = 89.736 (1)° |
Siemens SMART CCD area-detector diffractometer | 3482 reflections with I > 2σ(I) |
5771 measured reflections | Rint = 0.016 |
4110 independent reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 1.08 | Δρmax = 0.20 e Å−3 |
4110 reflections | Δρmin = −0.19 e Å−3 |
374 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 | ||
O1 | 1.08581 (13) | 0.64435 (8) | 0.98562 (8) | 0.0474 (3) | |
O2 | 0.90521 (13) | 0.66549 (9) | 0.82385 (9) | 0.0516 (3) | |
O3 | 0.85720 (19) | 0.78044 (15) | 0.58936 (11) | 0.0969 (5) | |
N1 | 0.97931 (14) | 0.85379 (10) | 0.93414 (10) | 0.0432 (3) | |
C1 | 0.98666 (17) | 0.81986 (13) | 0.82579 (12) | 0.0426 (3) | |
C2 | 1.03276 (16) | 0.75302 (12) | 1.01582 (11) | 0.0405 (3) | |
C3 | 1.06025 (17) | 0.67794 (12) | 0.85985 (11) | 0.0430 (3) | |
C4 | 1.21255 (18) | 0.60787 (12) | 0.81193 (12) | 0.0454 (3) | |
C5 | 1.3727 (2) | 0.59056 (17) | 0.85888 (15) | 0.0631 (4) | |
C6 | 1.5136 (2) | 0.5288 (2) | 0.81309 (18) | 0.0765 (6) | |
C7 | 1.4954 (3) | 0.48210 (18) | 0.72151 (17) | 0.0731 (5) | |
C8 | 1.3372 (2) | 0.50072 (17) | 0.67356 (16) | 0.0666 (5) | |
C9 | 1.1951 (2) | 0.56434 (14) | 0.71752 (14) | 0.0535 (4) | |
C10 | 1.04697 (16) | 0.73900 (13) | 1.14238 (12) | 0.0425 (3) | |
C11 | 1.0550 (2) | 0.83739 (15) | 1.18159 (14) | 0.0529 (4) | |
C12 | 1.0688 (2) | 0.82331 (18) | 1.30035 (15) | 0.0644 (4) | |
C13 | 1.0712 (2) | 0.71390 (19) | 1.37997 (15) | 0.0665 (5) | |
C14 | 1.0635 (3) | 0.61655 (19) | 1.34128 (15) | 0.0690 (5) | |
C15 | 1.0529 (2) | 0.62783 (16) | 1.22244 (14) | 0.0570 (4) | |
C16 | 0.82167 (18) | 0.79788 (14) | 0.78354 (12) | 0.0469 (3) | |
C17 | 0.79287 (19) | 0.84497 (17) | 0.65087 (14) | 0.0587 (4) | |
C18 | 0.69292 (19) | 0.97626 (16) | 0.60449 (13) | 0.0563 (4) | |
C19 | 0.7150 (3) | 1.0433 (2) | 0.49258 (16) | 0.0713 (5) | |
C20 | 0.6258 (3) | 1.1661 (2) | 0.4495 (2) | 0.0845 (6) | |
C21 | 0.5138 (3) | 1.2228 (2) | 0.5172 (2) | 0.0870 (6) | |
C22 | 0.4880 (3) | 1.15793 (19) | 0.62716 (19) | 0.0745 (5) | |
C23 | 0.57677 (19) | 1.03246 (15) | 0.67361 (14) | 0.0551 (4) | |
C24 | 0.54650 (18) | 0.95677 (15) | 0.78832 (14) | 0.0532 (4) | |
C25 | 0.4010 (2) | 0.9967 (2) | 0.84388 (18) | 0.0679 (5) | |
C26 | 0.3734 (3) | 0.9247 (2) | 0.9491 (2) | 0.0780 (6) | |
C27 | 0.4883 (3) | 0.8113 (2) | 1.00138 (18) | 0.0732 (5) | |
C28 | 0.6343 (2) | 0.76805 (18) | 0.94782 (15) | 0.0604 (4) | |
C29 | 0.66309 (18) | 0.84068 (15) | 0.84179 (13) | 0.0494 (3) | |
H1 | 1.0359 (18) | 0.8693 (13) | 0.7644 (13) | 0.041 (4)* | |
H5 | 1.386 (2) | 0.6223 (17) | 0.9221 (17) | 0.075 (5)* | |
H6 | 1.625 (3) | 0.520 (2) | 0.8462 (19) | 0.092 (7)* | |
H7 | 1.589 (3) | 0.4390 (19) | 0.6928 (18) | 0.082 (6)* | |
H8 | 1.324 (3) | 0.4689 (18) | 0.6075 (19) | 0.082 (6)* | |
H9 | 1.081 (2) | 0.5797 (16) | 0.6823 (16) | 0.069 (5)* | |
H11 | 1.050 (2) | 0.9136 (17) | 1.1238 (16) | 0.065 (5)* | |
H12 | 1.073 (2) | 0.8896 (18) | 1.3272 (17) | 0.076 (6)* | |
H13 | 1.079 (2) | 0.7062 (17) | 1.4609 (18) | 0.077 (6)* | |
H14 | 1.071 (3) | 0.534 (2) | 1.4001 (19) | 0.088 (6)* | |
H15 | 1.049 (2) | 0.5582 (18) | 1.1932 (17) | 0.073 (5)* | |
H19 | 0.790 (2) | 0.9980 (18) | 0.4487 (17) | 0.073 (6)* | |
H20 | 0.642 (3) | 1.211 (2) | 0.372 (2) | 0.108 (8)* | |
H21 | 0.452 (3) | 1.312 (2) | 0.485 (2) | 0.110 (8)* | |
H22 | 0.403 (3) | 1.199 (2) | 0.672 (2) | 0.094 (7)* | |
H25 | 0.316 (3) | 1.078 (2) | 0.8064 (19) | 0.089 (6)* | |
H26 | 0.275 (3) | 0.953 (2) | 0.9878 (19) | 0.090 (6)* | |
H27 | 0.472 (3) | 0.759 (2) | 1.075 (2) | 0.090 (7)* | |
H28 | 0.715 (2) | 0.6907 (17) | 0.9787 (15) | 0.059 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0659 (6) | 0.0389 (5) | 0.0360 (5) | −0.0129 (4) | 0.0062 (4) | −0.0122 (4) |
O2 | 0.0535 (6) | 0.0510 (6) | 0.0561 (6) | −0.0175 (5) | 0.0062 (5) | −0.0235 (5) |
O3 | 0.0951 (10) | 0.1126 (11) | 0.0513 (7) | 0.0254 (8) | −0.0011 (7) | −0.0376 (7) |
N1 | 0.0474 (6) | 0.0415 (6) | 0.0423 (6) | −0.0140 (5) | 0.0048 (5) | −0.0145 (5) |
C1 | 0.0445 (7) | 0.0424 (7) | 0.0387 (7) | −0.0115 (6) | 0.0056 (5) | −0.0101 (6) |
C2 | 0.0422 (7) | 0.0414 (7) | 0.0423 (7) | −0.0156 (6) | 0.0082 (5) | −0.0162 (6) |
C3 | 0.0499 (7) | 0.0434 (7) | 0.0357 (7) | −0.0136 (6) | 0.0037 (5) | −0.0125 (5) |
C4 | 0.0536 (8) | 0.0383 (7) | 0.0389 (7) | −0.0079 (6) | 0.0041 (6) | −0.0098 (5) |
C5 | 0.0570 (9) | 0.0701 (11) | 0.0548 (9) | −0.0014 (8) | −0.0040 (7) | −0.0266 (8) |
C6 | 0.0527 (10) | 0.0897 (14) | 0.0727 (12) | 0.0038 (9) | −0.0028 (9) | −0.0292 (10) |
C7 | 0.0657 (11) | 0.0695 (11) | 0.0676 (11) | 0.0067 (9) | 0.0143 (9) | −0.0248 (9) |
C8 | 0.0775 (12) | 0.0648 (11) | 0.0578 (10) | −0.0115 (9) | 0.0136 (9) | −0.0302 (8) |
C9 | 0.0613 (9) | 0.0534 (9) | 0.0485 (8) | −0.0156 (7) | 0.0091 (7) | −0.0218 (7) |
C10 | 0.0408 (7) | 0.0498 (8) | 0.0404 (7) | −0.0153 (6) | 0.0081 (5) | −0.0174 (6) |
C11 | 0.0586 (9) | 0.0521 (9) | 0.0510 (8) | −0.0151 (7) | 0.0053 (7) | −0.0222 (7) |
C12 | 0.0736 (11) | 0.0702 (11) | 0.0571 (10) | −0.0171 (9) | 0.0050 (8) | −0.0365 (9) |
C13 | 0.0696 (11) | 0.0920 (14) | 0.0418 (8) | −0.0213 (9) | 0.0116 (7) | −0.0298 (9) |
C14 | 0.0891 (13) | 0.0810 (13) | 0.0429 (9) | −0.0386 (10) | 0.0156 (8) | −0.0140 (8) |
C15 | 0.0745 (11) | 0.0620 (10) | 0.0442 (8) | −0.0333 (8) | 0.0120 (7) | −0.0177 (7) |
C16 | 0.0457 (7) | 0.0525 (8) | 0.0440 (7) | −0.0127 (6) | 0.0043 (6) | −0.0191 (6) |
C17 | 0.0457 (8) | 0.0797 (11) | 0.0469 (8) | −0.0067 (8) | 0.0024 (6) | −0.0264 (8) |
C18 | 0.0481 (8) | 0.0724 (10) | 0.0476 (8) | −0.0153 (7) | −0.0027 (6) | −0.0196 (7) |
C19 | 0.0682 (11) | 0.0910 (14) | 0.0502 (9) | −0.0203 (10) | 0.0012 (8) | −0.0183 (9) |
C20 | 0.0982 (16) | 0.0856 (15) | 0.0619 (12) | −0.0316 (13) | −0.0036 (11) | −0.0053 (11) |
C21 | 0.0973 (16) | 0.0685 (13) | 0.0815 (15) | −0.0177 (12) | −0.0035 (12) | −0.0084 (11) |
C22 | 0.0709 (12) | 0.0674 (12) | 0.0811 (13) | −0.0126 (9) | 0.0052 (10) | −0.0247 (10) |
C23 | 0.0461 (8) | 0.0636 (10) | 0.0573 (9) | −0.0150 (7) | −0.0014 (7) | −0.0222 (7) |
C24 | 0.0425 (7) | 0.0656 (10) | 0.0590 (9) | −0.0173 (7) | 0.0061 (6) | −0.0295 (8) |
C25 | 0.0480 (9) | 0.0800 (13) | 0.0818 (12) | −0.0176 (9) | 0.0163 (8) | −0.0357 (10) |
C26 | 0.0579 (11) | 0.0999 (16) | 0.0936 (15) | −0.0319 (11) | 0.0328 (10) | −0.0480 (13) |
C27 | 0.0767 (12) | 0.0946 (15) | 0.0687 (12) | −0.0479 (12) | 0.0312 (10) | −0.0330 (11) |
C28 | 0.0625 (10) | 0.0700 (11) | 0.0579 (10) | −0.0283 (9) | 0.0129 (8) | −0.0246 (8) |
C29 | 0.0456 (7) | 0.0637 (9) | 0.0492 (8) | −0.0224 (7) | 0.0088 (6) | −0.0271 (7) |
O1—C2 | 1.376 (2) | C13—C14 | 1.374 (3) |
O1—C3 | 1.440 (2) | C13—H13 | 0.94 (2) |
O2—C3 | 1.427 (2) | C14—C15 | 1.386 (2) |
O2—C16 | 1.453 (2) | C14—H14 | 1.02 (2) |
O3—C17 | 1.210 (2) | C15—H15 | 0.99 (2) |
N1—C2 | 1.273 (2) | C16—C29 | 1.506 (2) |
N1—C1 | 1.449 (2) | C16—C17 | 1.519 (2) |
C1—C3 | 1.543 (2) | C17—C18 | 1.475 (2) |
C1—C16 | 1.586 (2) | C18—C19 | 1.397 (2) |
C1—H1 | 0.98 (1) | C18—C23 | 1.401 (2) |
C2—C10 | 1.472 (2) | C19—C20 | 1.370 (3) |
C3—C4 | 1.498 (2) | C19—H19 | 0.95 (2) |
C4—C9 | 1.384 (2) | C20—C21 | 1.373 (3) |
C4—C5 | 1.386 (2) | C20—H20 | 0.97 (3) |
C5—C6 | 1.381 (2) | C21—C22 | 1.379 (3) |
C5—H5 | 0.95 (2) | C21—H21 | 0.99 (3) |
C6—C7 | 1.380 (3) | C22—C23 | 1.399 (3) |
C6—H6 | 0.98 (2) | C22—H22 | 0.97 (2) |
C7—C8 | 1.371 (3) | C23—C24 | 1.484 (2) |
C7—H7 | 0.92 (2) | C24—C25 | 1.397 (2) |
C8—C9 | 1.385 (2) | C24—C29 | 1.401 (2) |
C8—H8 | 0.98 (2) | C25—C26 | 1.373 (3) |
C9—H9 | 0.98 (2) | C25—H25 | 1.00 (2) |
C10—C15 | 1.388 (2) | C26—C27 | 1.373 (3) |
C10—C11 | 1.390 (2) | C26—H26 | 0.95 (2) |
C11—C12 | 1.379 (2) | C27—C28 | 1.395 (3) |
C11—H11 | 0.97 (2) | C27—H27 | 0.96 (2) |
C12—C13 | 1.377 (3) | C28—C29 | 1.387 (2) |
C12—H12 | 0.93 (2) | C28—H28 | 0.94 (2) |
C2—O1—C3 | 106.21 (10) | C15—C14—H14 | 119.5 (12) |
C3—O2—C16 | 93.61 (10) | C14—C15—C10 | 119.59 (16) |
C2—N1—C1 | 106.09 (11) | C14—C15—H15 | 121.4 (11) |
N1—C1—C3 | 106.41 (11) | C10—C15—H15 | 119.0 (11) |
N1—C1—C16 | 115.48 (11) | O2—C16—C29 | 113.76 (12) |
C3—C1—C16 | 84.30 (10) | O2—C16—C17 | 111.97 (12) |
N1—C1—H1 | 113.5 (8) | C29—C16—C17 | 112.09 (12) |
C3—C1—H1 | 119.1 (8) | O2—C16—C1 | 89.65 (10) |
C16—C1—H1 | 114.9 (8) | C29—C16—C1 | 117.80 (11) |
N1—C2—O1 | 118.30 (12) | C17—C16—C1 | 109.71 (12) |
N1—C2—C10 | 126.70 (12) | O3—C17—C18 | 123.45 (15) |
O1—C2—C10 | 114.99 (11) | O3—C17—C16 | 121.60 (15) |
O2—C3—O1 | 110.99 (10) | C18—C17—C16 | 114.79 (13) |
O2—C3—C4 | 114.51 (11) | C19—C18—C23 | 120.70 (17) |
O1—C3—C4 | 109.77 (11) | C19—C18—C17 | 119.86 (16) |
O2—C3—C1 | 92.36 (10) | C23—C18—C17 | 119.44 (14) |
O1—C3—C1 | 102.96 (10) | C20—C19—C18 | 120.5 (2) |
C4—C3—C1 | 124.72 (11) | C20—C19—H19 | 123.4 (12) |
C9—C4—C5 | 119.37 (14) | C18—C19—H19 | 116.1 (12) |
C9—C4—C3 | 120.52 (13) | C19—C20—C21 | 119.4 (2) |
C5—C4—C3 | 120.05 (13) | C19—C20—H20 | 119.6 (15) |
C6—C5—C4 | 120.31 (17) | C21—C20—H20 | 121.0 (15) |
C6—C5—H5 | 119.7 (12) | C20—C21—C22 | 121.1 (2) |
C4—C5—H5 | 120.0 (12) | C20—C21—H21 | 118.0 (15) |
C7—C6—C5 | 120.05 (19) | C22—C21—H21 | 120.8 (15) |
C7—C6—H6 | 121.1 (13) | C21—C22—C23 | 120.9 (2) |
C5—C6—H6 | 118.8 (13) | C21—C22—H22 | 119.8 (13) |
C8—C7—C6 | 119.83 (17) | C23—C22—H22 | 119.3 (13) |
C8—C7—H7 | 120.4 (13) | C22—C23—C18 | 117.40 (17) |
C6—C7—H7 | 119.8 (13) | C22—C23—C24 | 123.02 (16) |
C7—C8—C9 | 120.58 (17) | C18—C23—C24 | 119.50 (15) |
C7—C8—H8 | 119.8 (12) | C25—C24—C29 | 118.46 (16) |
C9—C8—H8 | 119.6 (12) | C25—C24—C23 | 121.60 (16) |
C4—C9—C8 | 119.82 (16) | C29—C24—C23 | 119.92 (13) |
C4—C9—H9 | 119.2 (11) | C26—C25—C24 | 120.96 (19) |
C8—C9—H9 | 120.9 (11) | C26—C25—H25 | 119.7 (13) |
C15—C10—C11 | 120.01 (14) | C24—C25—H25 | 119.3 (13) |
C15—C10—C2 | 120.19 (13) | C27—C26—C25 | 120.36 (18) |
C11—C10—C2 | 119.80 (13) | C27—C26—H26 | 118.7 (13) |
C12—C11—C10 | 119.41 (16) | C25—C26—H26 | 120.9 (13) |
C12—C11—H11 | 122.5 (11) | C26—C27—C28 | 120.21 (19) |
C10—C11—H11 | 118.1 (11) | C26—C27—H27 | 122.2 (13) |
C13—C12—C11 | 120.70 (17) | C28—C27—H27 | 117.6 (13) |
C13—C12—H12 | 119.5 (12) | C29—C28—C27 | 119.61 (19) |
C11—C12—H12 | 119.7 (12) | C29—C28—H28 | 116.8 (11) |
C14—C13—C12 | 119.92 (16) | C27—C28—H28 | 123.6 (11) |
C14—C13—H13 | 120.4 (12) | C28—C29—C24 | 120.39 (15) |
C12—C13—H13 | 119.6 (12) | C28—C29—C16 | 120.79 (15) |
C13—C14—C15 | 120.35 (17) | C24—C29—C16 | 118.80 (13) |
C13—C14—H14 | 120.1 (12) | ||
C2—N1—C1—C3 | −1.50 (14) | C3—C1—C16—O2 | 1.97 (9) |
C2—N1—C1—C16 | 89.97 (14) | N1—C1—C16—C29 | 13.38 (18) |
C1—N1—C2—O1 | 1.84 (16) | C3—C1—C16—C29 | 118.86 (13) |
C1—N1—C2—C10 | −179.09 (12) | N1—C1—C16—C17 | 143.21 (12) |
C3—O1—C2—N1 | −1.36 (16) | C3—C1—C16—C17 | −111.31 (12) |
C3—O1—C2—C10 | 179.47 (11) | O2—C16—C17—O3 | −10.6 (2) |
C16—O2—C3—O1 | 107.03 (11) | C29—C16—C17—O3 | −139.84 (18) |
C16—O2—C3—C4 | −128.00 (12) | C1—C16—C17—O3 | 87.3 (2) |
C16—O2—C3—C1 | 2.19 (10) | O2—C16—C17—C18 | 173.94 (12) |
C2—O1—C3—O2 | −97.46 (12) | C29—C16—C17—C18 | 44.69 (18) |
C2—O1—C3—C4 | 134.95 (11) | C1—C16—C17—C18 | −88.16 (15) |
C2—O1—C3—C1 | 0.22 (13) | O3—C17—C18—C19 | −22.2 (3) |
N1—C1—C3—O2 | 112.91 (11) | C16—C17—C18—C19 | 153.13 (15) |
C16—C1—C3—O2 | −2.0 (1) | O3—C17—C18—C23 | 157.90 (18) |
N1—C1—C3—O1 | 0.8 (1) | C16—C17—C18—C23 | −26.7 (2) |
C16—C1—C3—O1 | −114.18 (11) | C23—C18—C19—C20 | 1.4 (3) |
N1—C1—C3—C4 | −124.83 (13) | C17—C18—C19—C20 | −178.45 (17) |
C16—C1—C3—C4 | 120.25 (14) | C18—C19—C20—C21 | −0.3 (3) |
O2—C3—C4—C9 | 16.42 (19) | C19—C20—C21—C22 | −0.8 (4) |
O1—C3—C4—C9 | 142.02 (13) | C20—C21—C22—C23 | 0.7 (4) |
C1—C3—C4—C9 | −95.36 (17) | C21—C22—C23—C18 | 0.4 (3) |
O2—C3—C4—C5 | −166.27 (14) | C21—C22—C23—C24 | −176.27 (18) |
O1—C3—C4—C5 | −40.67 (18) | C19—C18—C23—C22 | −1.5 (2) |
C1—C3—C4—C5 | 81.95 (18) | C17—C18—C23—C22 | 178.39 (15) |
C9—C4—C5—C6 | −1.0 (3) | C19—C18—C23—C24 | 175.37 (15) |
C3—C4—C5—C6 | −178.33 (17) | C17—C18—C23—C24 | −4.8 (2) |
C4—C5—C6—C7 | −1.1 (3) | C22—C23—C24—C25 | 16.2 (2) |
C5—C6—C7—C8 | 2.2 (3) | C18—C23—C24—C25 | −160.47 (15) |
C6—C7—C8—C9 | −1.1 (3) | C22—C23—C24—C29 | −165.68 (15) |
C5—C4—C9—C8 | 2.1 (2) | C18—C23—C24—C29 | 17.7 (2) |
C3—C4—C9—C8 | 179.40 (14) | C29—C24—C25—C26 | 0.8 (3) |
C7—C8—C9—C4 | −1.0 (3) | C23—C24—C25—C26 | 178.93 (17) |
N1—C2—C10—C15 | 158.65 (15) | C24—C25—C26—C27 | −0.5 (3) |
O1—C2—C10—C15 | −22.26 (19) | C25—C26—C27—C28 | −0.1 (3) |
N1—C2—C10—C11 | −21.5 (2) | C26—C27—C28—C29 | 0.4 (3) |
O1—C2—C10—C11 | 157.56 (13) | C27—C28—C29—C24 | −0.1 (2) |
C15—C10—C11—C12 | 0.0 (2) | C27—C28—C29—C16 | 178.35 (15) |
C2—C10—C11—C12 | −179.80 (14) | C25—C24—C29—C28 | −0.4 (2) |
C10—C11—C12—C13 | −1.4 (3) | C23—C24—C29—C28 | −178.63 (14) |
C11—C12—C13—C14 | 1.4 (3) | C25—C24—C29—C16 | −178.96 (14) |
C12—C13—C14—C15 | −0.1 (3) | C23—C24—C29—C16 | 2.8 (2) |
C13—C14—C15—C10 | −1.2 (3) | O2—C16—C29—C28 | 20.00 (19) |
C11—C10—C15—C14 | 1.3 (2) | C17—C16—C29—C28 | 148.30 (15) |
C2—C10—C15—C14 | −178.93 (15) | C1—C16—C29—C28 | −82.98 (18) |
C3—O2—C16—C29 | −122.58 (12) | O2—C16—C29—C24 | −161.49 (12) |
C3—O2—C16—C17 | 109.05 (12) | C17—C16—C29—C24 | −33.18 (19) |
C3—O2—C16—C1 | −2.13 (10) | C1—C16—C29—C24 | 95.53 (16) |
N1—C1—C16—O2 | −103.51 (12) |
Experimental details
Crystal data | |
Chemical formula | C29H19NO3 |
Mr | 429.45 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.3475 (4), 11.8671 (6), 11.9106 (6) |
α, β, γ (°) | 74.148 (1), 89.736 (1), 72.344 (1) |
V (Å3) | 1077.59 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.40 × 0.30 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5771, 4110, 3482 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.117, 1.08 |
No. of reflections | 4110 |
No. of parameters | 374 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.20, −0.19 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 1996), SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
O1—C2 | 1.376 (2) | N1—C1 | 1.449 (2) |
O1—C3 | 1.440 (2) | C1—C3 | 1.543 (2) |
O2—C3 | 1.427 (2) | C1—C16 | 1.586 (2) |
O2—C16 | 1.453 (2) | C16—C29 | 1.506 (2) |
N1—C2 | 1.273 (2) | C16—C17 | 1.519 (2) |
C16—C1—C3—O2 | −2.0 (1) | N1—C1—C16—C29 | 13.38 (18) |
N1—C1—C3—O1 | 0.8 (1) |
In our ongoing research on the photocycloaddition reactions of α-dicarbonyl compounds with oxazole derivatives (Zhang et al., 2003), we have carried out the photoreactions of 9,10-phenanthrenedione with 2,5-diphenyloxazole and isolated the title compound, (I). We have also structurally analysed (I) and the results are presented here.
The bond lengths and angles in (I) (Fig. 1) are within normal ranges (Allen et al., 1987). Those within the spiroxetane–oxazole system (C1/C16/O2/C3/O1,/2/N1) are comparable to the corresponding values in the related structure, spiro[indole-3,2'-(2'aH,5'aH)oxeto[5,4-b]oxazol]-2(1H)-one derivatives (Usman et al., 2003). Similar to these related structures are the elongation of Csp3—Csp3 for the C1–C16 moiety and the planarity of the spiroxetane ring. The dihedral angle between the O2/C3/C1 and O2/C1/C16 planes is 177.0 (1)° [176.9 (3)–178.6 (2)°; Usman et al., 2003].
The planes through the oxetane and oxazole rings make a dihedral angle of 113.4 (1)°. This is conditioned by the eclipsed configuration of the sp3 state of the shared atoms C1 and C3. The relative configurations of the phenyl rings C4–C9 and C10–C15 with respect to the oxetane-oxazole system are determined by their attached atoms C3 (sp3) and C2 (sp2), respectively. The two phenyl rings make dihedral angles of 68.1 (1) and 22.4 (1)°, respectively, with the oxazole.
The phenanthrene is out of planarity with its dihydrobenzene ring (C16–C18/C23/C24/C29) having a half-chair conformation. Atoms C16 and C17 by 0.209 (2) and 0.374 (2) Å in opposite directions from the C18/C23/C24/C29 plane. This plane makes dihedral angles of 11.8 (1) and 8.0 (1)° with the fused benzene rings C18–C23 and C24–C29, respectively. The dihydrobenzene mean plane is nearly orthogonal to the oxetane ring with a dihedral angle of 82.2 (1)°. This is conditioned by the sp3 state of the shared atom C16. Ketone atom O3 attached to the C17 deviates by 0.715 (2) Å from the dihydrobenzene mean plane.