Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028278/ob6581sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028278/ob6581Isup2.hkl |
CCDC reference: 282603
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C)= 0.003 Å
- R factor = 0.035
- wR factor = 0.110
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
To a mixture of anthrone (2.0 g, 10 mmol) and 3,4-dimethoxybenzaldehyde (2.0 g, 12 mmol) were added pyridine (30 ml) and piperidine (0.5 g, 6 mmol). The reaction mixture was refluxed for 6 h and thin-layer chromatography showed that the reaction was complete. The mixture was cooled to room temperature, poured into methanol (75 ml) and placed in a refrigerator overnight. The precipitate which formed was collected and recrystallized twice from glacial acetic acid to afford orange crystals of (I) (2.4 g, yield 70.2%, m.p. 453–456 K). Crystals suitable for X-ray analysis were grown from an ethanol solution by slow evaparation.
H atoms were placed at calculated positions and refined using a riding model. H atoms were given isotropic displacement parameters equal to 1.2 times the equivalent isotropic displacement parameters of their parent atoms (1.5 for methyl H atoms) and C—H distances were constrained to 0.93 Å (0.96 Å for methyl H atoms).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD (McArdle, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C23H18O3 | F(000) = 720 |
Mr = 342.37 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/n | Melting point = 453–456 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 11.709 (3) Å | Cell parameters from 25 reflections |
b = 10.306 (2) Å | θ = 10.7–14.0° |
c = 14.847 (6) Å | µ = 0.09 mm−1 |
β = 103.36 (3)° | T = 295 K |
V = 1743.1 (9) Å3 | Prismatic, orange |
Z = 4 | 0.40 × 0.40 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.021 |
Radiation source: fine-focus sealed tube | θmax = 25.2°, θmin = 2.0° |
Graphite monochromator | h = −14→13 |
ω/2θ scans | k = 0→12 |
3529 measured reflections | l = −1→17 |
3136 independent reflections | 3 standard reflections every 60 min |
1832 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0484P)2 + 0.3183P] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
3136 reflections | Δρmax = 0.15 e Å−3 |
238 parameters | Δρmin = −0.13 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: 0.0133 (12) |
C23H18O3 | V = 1743.1 (9) Å3 |
Mr = 342.37 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.709 (3) Å | µ = 0.09 mm−1 |
b = 10.306 (2) Å | T = 295 K |
c = 14.847 (6) Å | 0.40 × 0.40 × 0.20 mm |
β = 103.36 (3)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.021 |
3529 measured reflections | 3 standard reflections every 60 min |
3136 independent reflections | intensity decay: none |
1832 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.15 e Å−3 |
3136 reflections | Δρmin = −0.13 e Å−3 |
238 parameters |
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 | −0.07769 (13) | 0.91670 (16) | 0.26699 (11) | 0.0853 (5) | |
O2 | 0.48952 (12) | 0.24924 (13) | 0.60172 (9) | 0.0618 (4) | |
O3 | 0.45078 (12) | 0.13957 (13) | 0.44370 (9) | 0.0628 (4) | |
C1 | 0.07187 (19) | 1.0518 (2) | 0.41341 (15) | 0.0614 (6) | |
H1 | 0.0141 | 1.1001 | 0.3740 | 0.074* | |
C2 | 0.1505 (2) | 1.1133 (2) | 0.48267 (16) | 0.0665 (6) | |
H2 | 0.1465 | 1.2026 | 0.4902 | 0.080* | |
C3 | 0.2351 (2) | 1.0416 (2) | 0.54095 (16) | 0.0669 (6) | |
H3 | 0.2884 | 1.0828 | 0.5886 | 0.080* | |
C4 | 0.24224 (17) | 0.90959 (18) | 0.52979 (15) | 0.0587 (5) | |
H4 | 0.3006 | 0.8631 | 0.5701 | 0.070* | |
C5 | 0.17147 (15) | 0.70174 (17) | 0.44396 (12) | 0.0448 (4) | |
C6 | 0.03917 (17) | 0.5061 (2) | 0.40338 (14) | 0.0565 (5) | |
H6 | 0.0957 | 0.4547 | 0.4414 | 0.068* | |
C7 | −0.0657 (2) | 0.4513 (2) | 0.35799 (16) | 0.0725 (7) | |
H7 | −0.0794 | 0.3636 | 0.3659 | 0.087* | |
C8 | −0.1508 (2) | 0.5259 (3) | 0.30062 (17) | 0.0828 (8) | |
H8 | −0.2210 | 0.4883 | 0.2694 | 0.099* | |
C9 | −0.13106 (18) | 0.6547 (3) | 0.29017 (16) | 0.0739 (7) | |
H9 | −0.1883 | 0.7047 | 0.2516 | 0.089* | |
C10 | −0.01277 (16) | 0.8539 (2) | 0.32866 (14) | 0.0576 (5) | |
C11 | 0.16388 (14) | 0.84343 (17) | 0.45934 (12) | 0.0454 (5) | |
C12 | 0.06211 (15) | 0.63806 (18) | 0.39324 (12) | 0.0451 (4) | |
C13 | −0.02637 (15) | 0.7128 (2) | 0.33644 (13) | 0.0523 (5) | |
C14 | 0.07668 (16) | 0.91733 (18) | 0.40075 (13) | 0.0481 (5) | |
C15 | 0.27495 (15) | 0.64083 (18) | 0.47521 (14) | 0.0533 (5) | |
H15 | 0.3329 | 0.6926 | 0.5114 | 0.064* | |
C16 | 0.31284 (15) | 0.50738 (18) | 0.46252 (13) | 0.0489 (5) | |
C17 | 0.38052 (15) | 0.44288 (18) | 0.53917 (13) | 0.0476 (5) | |
H17 | 0.3966 | 0.4832 | 0.5968 | 0.057* | |
C18 | 0.42387 (15) | 0.32021 (17) | 0.53070 (13) | 0.0467 (5) | |
C19 | 0.40288 (16) | 0.25983 (18) | 0.44413 (13) | 0.0494 (5) | |
C20 | 0.33782 (16) | 0.3241 (2) | 0.36780 (14) | 0.0546 (5) | |
H20 | 0.3239 | 0.2850 | 0.3098 | 0.066* | |
C21 | 0.29319 (17) | 0.4466 (2) | 0.37722 (14) | 0.0570 (5) | |
H21 | 0.2492 | 0.4887 | 0.3253 | 0.068* | |
C22 | 0.5087 (2) | 0.3023 (2) | 0.69236 (13) | 0.0698 (6) | |
H22A | 0.5503 | 0.3829 | 0.6946 | 0.105* | |
H22B | 0.5542 | 0.2426 | 0.7359 | 0.105* | |
H22C | 0.4346 | 0.3172 | 0.7078 | 0.105* | |
C23 | 0.4107 (2) | 0.0596 (2) | 0.36466 (14) | 0.0699 (6) | |
H23A | 0.3265 | 0.0549 | 0.3507 | 0.105* | |
H23B | 0.4429 | −0.0260 | 0.3771 | 0.105* | |
H23C | 0.4356 | 0.0958 | 0.3128 | 0.105* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0625 (9) | 0.1013 (13) | 0.0794 (11) | 0.0244 (9) | −0.0095 (8) | 0.0270 (9) |
O2 | 0.0731 (9) | 0.0504 (8) | 0.0519 (8) | 0.0149 (7) | −0.0063 (7) | 0.0021 (6) |
O3 | 0.0668 (9) | 0.0524 (9) | 0.0625 (9) | 0.0157 (7) | 0.0013 (7) | −0.0076 (7) |
C1 | 0.0639 (13) | 0.0565 (13) | 0.0679 (14) | 0.0192 (11) | 0.0233 (12) | 0.0193 (11) |
C2 | 0.0793 (15) | 0.0455 (12) | 0.0806 (16) | 0.0017 (11) | 0.0310 (13) | 0.0040 (12) |
C3 | 0.0685 (14) | 0.0534 (13) | 0.0768 (15) | −0.0080 (11) | 0.0126 (12) | −0.0049 (11) |
C4 | 0.0511 (11) | 0.0513 (13) | 0.0680 (14) | 0.0001 (10) | 0.0022 (10) | 0.0022 (10) |
C5 | 0.0391 (10) | 0.0456 (11) | 0.0468 (10) | 0.0013 (8) | 0.0038 (8) | 0.0056 (8) |
C6 | 0.0514 (11) | 0.0573 (12) | 0.0617 (13) | −0.0074 (10) | 0.0146 (10) | −0.0070 (10) |
C7 | 0.0646 (14) | 0.0737 (15) | 0.0836 (16) | −0.0243 (13) | 0.0260 (13) | −0.0247 (13) |
C8 | 0.0466 (12) | 0.108 (2) | 0.0897 (18) | −0.0194 (15) | 0.0080 (12) | −0.0369 (17) |
C9 | 0.0409 (11) | 0.105 (2) | 0.0680 (15) | 0.0044 (13) | −0.0044 (10) | −0.0178 (14) |
C10 | 0.0402 (10) | 0.0776 (15) | 0.0537 (13) | 0.0170 (11) | 0.0084 (9) | 0.0113 (11) |
C11 | 0.0383 (9) | 0.0463 (11) | 0.0506 (11) | 0.0025 (9) | 0.0082 (8) | 0.0060 (9) |
C12 | 0.0369 (9) | 0.0536 (12) | 0.0439 (10) | 0.0004 (9) | 0.0078 (8) | −0.0030 (9) |
C13 | 0.0367 (10) | 0.0701 (14) | 0.0479 (11) | 0.0040 (9) | 0.0054 (9) | −0.0040 (10) |
C14 | 0.0424 (10) | 0.0509 (12) | 0.0523 (11) | 0.0096 (9) | 0.0135 (9) | 0.0089 (9) |
C15 | 0.0420 (10) | 0.0475 (12) | 0.0626 (13) | 0.0007 (9) | −0.0040 (9) | 0.0010 (9) |
C16 | 0.0373 (9) | 0.0460 (11) | 0.0589 (12) | 0.0030 (8) | 0.0016 (9) | 0.0040 (9) |
C17 | 0.0412 (10) | 0.0457 (11) | 0.0512 (11) | 0.0002 (8) | 0.0010 (8) | −0.0023 (9) |
C18 | 0.0391 (9) | 0.0438 (11) | 0.0524 (11) | 0.0016 (8) | 0.0003 (8) | 0.0034 (9) |
C19 | 0.0433 (10) | 0.0477 (11) | 0.0550 (12) | 0.0048 (9) | 0.0071 (9) | 0.0010 (9) |
C20 | 0.0519 (11) | 0.0604 (13) | 0.0475 (11) | 0.0054 (10) | 0.0029 (9) | −0.0025 (10) |
C21 | 0.0492 (11) | 0.0601 (13) | 0.0552 (12) | 0.0092 (10) | −0.0012 (9) | 0.0093 (11) |
C22 | 0.0871 (16) | 0.0647 (14) | 0.0482 (12) | 0.0083 (12) | −0.0040 (11) | 0.0039 (11) |
C23 | 0.0906 (17) | 0.0575 (13) | 0.0605 (14) | 0.0118 (12) | 0.0149 (12) | −0.0117 (11) |
O1—C10 | 1.230 (2) | C9—C13 | 1.394 (3) |
O2—C18 | 1.365 (2) | C9—H9 | 0.9300 |
O2—C22 | 1.421 (2) | C10—C14 | 1.467 (3) |
O3—C19 | 1.361 (2) | C10—C13 | 1.471 (3) |
O3—C23 | 1.422 (2) | C11—C14 | 1.403 (2) |
C1—C2 | 1.367 (3) | C12—C13 | 1.405 (2) |
C1—C14 | 1.401 (3) | C15—C16 | 1.471 (3) |
C1—H1 | 0.9300 | C15—H15 | 0.9300 |
C2—C3 | 1.371 (3) | C16—C21 | 1.384 (3) |
C2—H2 | 0.9300 | C16—C17 | 1.396 (2) |
C3—C4 | 1.376 (3) | C17—C18 | 1.379 (2) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C11 | 1.399 (3) | C18—C19 | 1.398 (3) |
C4—H4 | 0.9300 | C19—C20 | 1.380 (3) |
C5—C15 | 1.348 (2) | C20—C21 | 1.386 (3) |
C5—C12 | 1.480 (2) | C20—H20 | 0.9300 |
C5—C11 | 1.484 (3) | C21—H21 | 0.9300 |
C6—C7 | 1.378 (3) | C22—H22A | 0.9599 |
C6—C12 | 1.401 (3) | C22—H22B | 0.9599 |
C6—H6 | 0.9300 | C22—H22C | 0.9599 |
C7—C8 | 1.385 (3) | C23—H23A | 0.9599 |
C7—H7 | 0.9300 | C23—H23B | 0.9599 |
C8—C9 | 1.362 (3) | C23—H23C | 0.9599 |
C8—H8 | 0.9300 | ||
C18—O2—C22 | 117.57 (15) | C9—C13—C10 | 118.97 (19) |
C19—O3—C23 | 118.29 (15) | C12—C13—C10 | 120.73 (17) |
C2—C1—C14 | 121.2 (2) | C1—C14—C11 | 119.97 (19) |
C2—C1—H1 | 119.4 | C1—C14—C10 | 119.62 (18) |
C14—C1—H1 | 119.4 | C11—C14—C10 | 120.35 (17) |
C1—C2—C3 | 119.2 (2) | C5—C15—C16 | 131.69 (18) |
C1—C2—H2 | 120.4 | C5—C15—H15 | 114.2 |
C3—C2—H2 | 120.4 | C16—C15—H15 | 114.2 |
C2—C3—C4 | 120.8 (2) | C21—C16—C17 | 118.28 (17) |
C2—C3—H3 | 119.6 | C21—C16—C15 | 123.32 (17) |
C4—C3—H3 | 119.6 | C17—C16—C15 | 118.17 (18) |
C3—C4—C11 | 121.65 (19) | C18—C17—C16 | 120.92 (18) |
C3—C4—H4 | 119.2 | C18—C17—H17 | 119.5 |
C11—C4—H4 | 119.2 | C16—C17—H17 | 119.5 |
C15—C5—C12 | 124.86 (17) | O2—C18—C17 | 125.05 (17) |
C15—C5—C11 | 119.09 (16) | O2—C18—C19 | 114.82 (16) |
C12—C5—C11 | 116.04 (15) | C17—C18—C19 | 120.12 (17) |
C7—C6—C12 | 121.1 (2) | O3—C19—C20 | 125.66 (18) |
C7—C6—H6 | 119.4 | O3—C19—C18 | 115.12 (16) |
C12—C6—H6 | 119.4 | C20—C19—C18 | 119.21 (18) |
C6—C7—C8 | 120.4 (2) | C19—C20—C21 | 120.25 (19) |
C6—C7—H7 | 119.8 | C19—C20—H20 | 119.9 |
C8—C7—H7 | 119.8 | C21—C20—H20 | 119.9 |
C9—C8—C7 | 119.6 (2) | C16—C21—C20 | 121.20 (18) |
C9—C8—H8 | 120.2 | C16—C21—H21 | 119.4 |
C7—C8—H8 | 120.2 | C20—C21—H21 | 119.4 |
C8—C9—C13 | 121.0 (2) | O2—C22—H22A | 109.5 |
C8—C9—H9 | 119.5 | O2—C22—H22B | 109.5 |
C13—C9—H9 | 119.5 | H22A—C22—H22B | 109.5 |
O1—C10—C14 | 121.6 (2) | O2—C22—H22C | 109.5 |
O1—C10—C13 | 121.3 (2) | H22A—C22—H22C | 109.5 |
C14—C10—C13 | 117.08 (16) | H22B—C22—H22C | 109.5 |
C4—C11—C14 | 117.16 (17) | O3—C23—H23A | 109.5 |
C4—C11—C5 | 122.85 (16) | O3—C23—H23B | 109.5 |
C14—C11—C5 | 119.97 (16) | H23A—C23—H23B | 109.5 |
C6—C12—C13 | 117.61 (18) | O3—C23—H23C | 109.5 |
C6—C12—C5 | 122.71 (17) | H23A—C23—H23C | 109.5 |
C13—C12—C5 | 119.57 (17) | H23B—C23—H23C | 109.5 |
C9—C13—C12 | 120.2 (2) | ||
C14—C1—C2—C3 | −0.3 (3) | C4—C11—C14—C1 | 0.9 (3) |
C1—C2—C3—C4 | 0.6 (3) | C5—C11—C14—C1 | −177.93 (17) |
C2—C3—C4—C11 | −0.2 (3) | C4—C11—C14—C10 | −176.50 (17) |
C12—C6—C7—C8 | 0.4 (3) | C5—C11—C14—C10 | 4.7 (3) |
C6—C7—C8—C9 | −0.9 (4) | O1—C10—C14—C1 | 14.9 (3) |
C7—C8—C9—C13 | 0.0 (4) | C13—C10—C14—C1 | −161.51 (17) |
C3—C4—C11—C14 | −0.6 (3) | O1—C10—C14—C11 | −167.72 (18) |
C3—C4—C11—C5 | 178.21 (19) | C13—C10—C14—C11 | 15.9 (3) |
C15—C5—C11—C4 | −22.9 (3) | C12—C5—C15—C16 | 6.5 (3) |
C12—C5—C11—C4 | 157.81 (17) | C11—C5—C15—C16 | −172.7 (2) |
C15—C5—C11—C14 | 155.82 (18) | C5—C15—C16—C21 | 48.2 (3) |
C12—C5—C11—C14 | −23.5 (2) | C5—C15—C16—C17 | −137.3 (2) |
C7—C6—C12—C13 | 1.0 (3) | C21—C16—C17—C18 | −1.9 (3) |
C7—C6—C12—C5 | 177.26 (18) | C15—C16—C17—C18 | −176.59 (16) |
C15—C5—C12—C6 | 26.4 (3) | C22—O2—C18—C17 | 4.1 (3) |
C11—C5—C12—C6 | −154.39 (17) | C22—O2—C18—C19 | −176.72 (18) |
C15—C5—C12—C13 | −157.46 (19) | C16—C17—C18—O2 | −179.21 (17) |
C11—C5—C12—C13 | 21.8 (2) | C16—C17—C18—C19 | 1.6 (3) |
C8—C9—C13—C12 | 1.5 (3) | C23—O3—C19—C20 | −15.3 (3) |
C8—C9—C13—C10 | −175.3 (2) | C23—O3—C19—C18 | 164.97 (18) |
C6—C12—C13—C9 | −2.0 (3) | O2—C18—C19—O3 | 0.1 (2) |
C5—C12—C13—C9 | −178.32 (17) | C17—C18—C19—O3 | 179.34 (16) |
C6—C12—C13—C10 | 174.80 (17) | O2—C18—C19—C20 | −179.68 (17) |
C5—C12—C13—C10 | −1.5 (3) | C17—C18—C19—C20 | −0.4 (3) |
O1—C10—C13—C9 | −17.1 (3) | O3—C19—C20—C21 | 179.76 (18) |
C14—C10—C13—C9 | 159.28 (18) | C18—C19—C20—C21 | −0.5 (3) |
O1—C10—C13—C12 | 166.05 (18) | C17—C16—C21—C20 | 0.9 (3) |
C14—C10—C13—C12 | −17.5 (3) | C15—C16—C21—C20 | 175.36 (18) |
C2—C1—C14—C11 | −0.5 (3) | C19—C20—C21—C16 | 0.2 (3) |
C2—C1—C14—C10 | 176.92 (18) |
Experimental details
Crystal data | |
Chemical formula | C23H18O3 |
Mr | 342.37 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 11.709 (3), 10.306 (2), 14.847 (6) |
β (°) | 103.36 (3) |
V (Å3) | 1743.1 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.40 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3529, 3136, 1832 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.110, 0.99 |
No. of reflections | 3136 |
No. of parameters | 238 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.13 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD (McArdle, 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.
O1—C10 | 1.230 (2) | C10—C14 | 1.467 (3) |
C5—C15 | 1.348 (2) | C10—C13 | 1.471 (3) |
C5—C12 | 1.480 (2) | C11—C14 | 1.403 (2) |
C5—C11 | 1.484 (3) | C12—C13 | 1.405 (2) |
C15—C5—C12 | 124.86 (17) | C21—C16—C15 | 123.32 (17) |
C15—C5—C11 | 119.09 (16) | C17—C16—C15 | 118.17 (18) |
C5—C15—C16 | 131.69 (18) | ||
C11—C5—C12—C13 | 21.8 (2) | C5—C11—C14—C10 | 4.7 (3) |
C5—C12—C13—C10 | −1.5 (3) | C12—C5—C15—C16 | 6.5 (3) |
C14—C10—C13—C12 | −17.5 (3) | C5—C15—C16—C21 | 48.2 (3) |
10-Substituted benzylideneanthrones have been known for a long time for their widespread use as functional dyes and disperse dyes (Day, 1963). Recently, however, some 10-substituted benzylideneanthrones have been found to possess high antitumor activity (Paull et al., 1992; Prinz et al., 2003). Owing to our interest in this area, we have prepared a series of 10-substituted benzylideneanthrones and evaluated their anticancer activity. Our study on the structure–activity relationship (SAR) showed that a substitutent in the benzene moiety of the molecule affects the antitumor activity (Hu & Zhou, 2004). In a continuation of our research on SAR, we prepared the title compound, (I), and investigated its structure.
The molecular structure of (I) is illustrated in Fig. 1, and selected bond lengths and angles are listed in Table 1. The three rings of the anthraquinone moiety are not coplanar, the dihedral angle between the two outer benzene rings being 24.68 (9)°. In the central six-membered ring, atoms C11/C12/C13/C14 are planar within 0.0083 (9) Å, atoms C5 and C10 deviating from the plane by 0.262 (3) and 0.190 (3) Å, respectively; the ring assumes an asymmetric boat conformation.