In the title compound, C24H18O2, the benzodifuran ring system is planar. The two phenyl rings make dihedral angles of 37.4 (2) and 40.8 (2)° with the benzodifuran ring system.
Supporting information
CCDC reference: 245299
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.084
- wR factor = 0.249
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: WinGX (Farrugia, 1999).
Crystal data top
C24H18O2 | Z = 2 |
Mr = 338.38 | F(000) = 356 |
Triclinic, P1 | Dx = 1.318 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6867 (19) Å | Cell parameters from 23 reflections |
b = 9.7435 (19) Å | θ = 8.3–15.8° |
c = 10.723 (2) Å | µ = 0.08 mm−1 |
α = 116.90 (3)° | T = 293 K |
β = 100.35 (3)° | Block, colorless |
γ = 99.36 (3)° | 0.26 × 0.2 × 0.17 mm |
V = 852.8 (4) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | θmax = 25.3°, θmin = 2.2° |
Non–profiled ω/2θ scans | h = 0→11 |
3278 measured reflections | k = −11→11 |
3080 independent reflections | l = −12→12 |
1234 reflections with I > 2σ(I) | 3 standard reflections every 400 reflections |
Rint = 0.051 | intensity decay: 2% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.085 | w = 1/[σ2(Fo2) + (0.1043P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.249 | (Δ/σ)max < 0.001 |
S = 0.98 | Δρmax = 0.35 e Å−3 |
3080 reflections | Δρmin = −0.25 e Å−3 |
235 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.2211 (4) | 0.9354 (5) | 0.4659 (4) | 0.0431 (12) | |
C2 | 0.2780 (7) | 1.0695 (7) | 0.6039 (7) | 0.0402 (17) | |
C3 | 0.2073 (6) | 1.0576 (7) | 0.6992 (6) | 0.0351 (15) | |
C4 | −0.0119 (6) | 0.8236 (7) | 0.6494 (6) | 0.0352 (15) | |
H4 | −0.0264 | 0.8663 | 0.7415 | 0.042* | |
O5 | −0.2075 (4) | 0.5783 (5) | 0.5433 (4) | 0.0399 (12) | |
C6 | −0.2624 (7) | 0.4441 (7) | 0.4069 (7) | 0.0380 (16) | |
C7 | −0.1917 (6) | 0.4533 (7) | 0.3132 (6) | 0.0317 (14) | |
C8 | 0.0274 (6) | 0.6888 (7) | 0.3605 (6) | 0.0373 (16) | |
H8 | 0.0408 | 0.6478 | 0.268 | 0.045* | |
C9 | 0.1100 (7) | 0.8343 (7) | 0.4744 (7) | 0.0384 (16) | |
C10 | 0.0970 (6) | 0.9051 (7) | 0.6174 (6) | 0.0345 (16) | |
C11 | −0.0949 (6) | 0.6777 (7) | 0.5365 (6) | 0.0305 (14) | |
C12 | −0.0795 (6) | 0.6055 (7) | 0.3933 (6) | 0.0343 (16) | |
C13 | 0.4006 (7) | 1.1912 (8) | 0.6142 (7) | 0.0518 (19) | |
H13A | 0.4185 | 1.1547 | 0.5207 | 0.078* | |
H13B | 0.4868 | 1.207 | 0.6849 | 0.078* | |
H13C | 0.3756 | 1.2905 | 0.6437 | 0.078* | |
C14 | 0.2379 (6) | 1.1751 (7) | 0.8545 (6) | 0.0322 (15) | |
C15 | 0.2687 (7) | 1.3386 (7) | 0.9044 (7) | 0.0420 (16) | |
H15 | 0.2719 | 1.3755 | 0.8384 | 0.05* | |
C16 | 0.2945 (8) | 1.4467 (8) | 1.0497 (7) | 0.0540 (19) | |
H16 | 0.3155 | 1.5556 | 1.0807 | 0.065* | |
C17 | 0.2898 (7) | 1.3956 (7) | 1.1511 (7) | 0.0436 (17) | |
H17 | 0.3064 | 1.4689 | 1.2492 | 0.052* | |
C18 | 0.2599 (6) | 1.2336 (7) | 1.1026 (6) | 0.0426 (16) | |
H18 | 0.2565 | 1.1973 | 1.1689 | 0.051* | |
C19 | 0.2348 (6) | 1.1244 (7) | 0.9569 (6) | 0.0377 (15) | |
H19 | 0.2156 | 1.0157 | 0.9266 | 0.045* | |
C20 | −0.3838 (7) | 0.3191 (8) | 0.3946 (7) | 0.0509 (19) | |
H20A | −0.4061 | 0.3561 | 0.4861 | 0.076* | |
H20B | −0.3549 | 0.2225 | 0.3699 | 0.076* | |
H20C | −0.4687 | 0.2981 | 0.3198 | 0.076* | |
C21 | −0.2221 (6) | 0.3349 (7) | 0.1567 (6) | 0.0307 (14) | |
C22 | −0.3622 (7) | 0.2495 (7) | 0.0666 (6) | 0.0403 (15) | |
H22 | −0.4408 | 0.2649 | 0.1051 | 0.048* | |
C23 | −0.3886 (7) | 0.1400 (7) | −0.0820 (7) | 0.0460 (17) | |
H23 | −0.4839 | 0.0835 | −0.1408 | 0.055* | |
C24 | −0.2750 (7) | 0.1162 (8) | −0.1404 (7) | 0.0466 (18) | |
H24 | −0.2924 | 0.0437 | −0.2388 | 0.056* | |
C25 | −0.1338 (8) | 0.2008 (8) | −0.0519 (7) | 0.0499 (18) | |
H25 | −0.0562 | 0.1857 | −0.0918 | 0.06* | |
C26 | −0.1063 (7) | 0.3078 (7) | 0.0951 (6) | 0.0405 (16) | |
H26 | −0.0105 | 0.362 | 0.1535 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.041 (3) | 0.044 (3) | 0.038 (2) | −0.007 (2) | 0.011 (2) | 0.020 (2) |
C2 | 0.043 (4) | 0.037 (4) | 0.038 (4) | 0.001 (3) | 0.005 (3) | 0.022 (3) |
C3 | 0.031 (3) | 0.039 (4) | 0.033 (3) | 0.002 (3) | 0.006 (3) | 0.020 (3) |
C4 | 0.036 (3) | 0.039 (4) | 0.031 (3) | 0.005 (3) | 0.010 (3) | 0.020 (3) |
O5 | 0.037 (2) | 0.035 (3) | 0.038 (2) | 0.000 (2) | 0.013 (2) | 0.013 (2) |
C6 | 0.032 (3) | 0.040 (4) | 0.034 (3) | 0.003 (3) | 0.009 (3) | 0.013 (3) |
C7 | 0.026 (3) | 0.032 (3) | 0.034 (3) | 0.009 (3) | 0.006 (3) | 0.014 (3) |
C8 | 0.035 (4) | 0.041 (4) | 0.027 (3) | 0.004 (3) | 0.010 (3) | 0.012 (3) |
C9 | 0.039 (4) | 0.036 (4) | 0.036 (4) | 0.003 (3) | 0.006 (3) | 0.018 (3) |
C10 | 0.032 (3) | 0.033 (4) | 0.027 (3) | 0.004 (3) | 0.000 (3) | 0.011 (3) |
C11 | 0.033 (3) | 0.032 (3) | 0.034 (3) | 0.007 (3) | 0.011 (3) | 0.023 (3) |
C12 | 0.034 (4) | 0.033 (4) | 0.031 (3) | 0.004 (3) | 0.010 (3) | 0.015 (3) |
C13 | 0.048 (4) | 0.052 (4) | 0.050 (4) | −0.007 (4) | 0.010 (4) | 0.029 (4) |
C14 | 0.022 (3) | 0.035 (4) | 0.033 (3) | 0.002 (3) | 0.001 (3) | 0.016 (3) |
C15 | 0.045 (4) | 0.035 (3) | 0.042 (4) | 0.009 (3) | 0.008 (3) | 0.018 (3) |
C16 | 0.066 (5) | 0.034 (4) | 0.053 (4) | 0.007 (3) | 0.010 (4) | 0.018 (4) |
C17 | 0.049 (4) | 0.034 (4) | 0.044 (4) | 0.009 (3) | 0.013 (3) | 0.018 (3) |
C18 | 0.043 (4) | 0.048 (4) | 0.033 (3) | 0.005 (3) | 0.011 (3) | 0.020 (3) |
C19 | 0.032 (3) | 0.039 (3) | 0.043 (4) | 0.006 (3) | 0.012 (3) | 0.021 (3) |
C20 | 0.049 (4) | 0.044 (4) | 0.042 (4) | −0.004 (3) | 0.013 (3) | 0.013 (3) |
C21 | 0.034 (3) | 0.029 (3) | 0.036 (3) | 0.008 (3) | 0.013 (3) | 0.021 (3) |
C22 | 0.037 (4) | 0.043 (4) | 0.041 (4) | 0.012 (3) | 0.015 (3) | 0.020 (3) |
C23 | 0.041 (4) | 0.039 (4) | 0.042 (4) | 0.001 (3) | 0.001 (3) | 0.014 (3) |
C24 | 0.052 (4) | 0.047 (4) | 0.034 (4) | 0.013 (4) | 0.014 (3) | 0.015 (3) |
C25 | 0.056 (4) | 0.056 (4) | 0.043 (4) | 0.021 (4) | 0.025 (3) | 0.024 (3) |
C26 | 0.032 (3) | 0.041 (4) | 0.046 (4) | 0.004 (3) | 0.008 (3) | 0.023 (3) |
Geometric parameters (Å, º) top
O1—C9 | 1.382 (7) | C14—C19 | 1.396 (8) |
O1—C2 | 1.387 (7) | C15—C16 | 1.375 (9) |
C2—C3 | 1.363 (8) | C15—H15 | 0.93 |
C2—C13 | 1.485 (8) | C16—C17 | 1.390 (8) |
C3—C10 | 1.445 (8) | C16—H16 | 0.93 |
C3—C14 | 1.469 (9) | C17—C18 | 1.379 (8) |
C4—C11 | 1.362 (8) | C17—H17 | 0.93 |
C4—C10 | 1.402 (8) | C18—C19 | 1.381 (8) |
C4—H4 | 0.93 | C18—H18 | 0.93 |
O5—C11 | 1.372 (6) | C19—H19 | 0.93 |
O5—C6 | 1.377 (7) | C20—H20A | 0.96 |
C6—C7 | 1.340 (8) | C20—H20B | 0.96 |
C6—C20 | 1.489 (8) | C20—H20C | 0.96 |
C7—C12 | 1.451 (7) | C21—C22 | 1.380 (8) |
C7—C21 | 1.482 (8) | C21—C26 | 1.403 (8) |
C8—C9 | 1.361 (8) | C22—C23 | 1.404 (9) |
C8—C12 | 1.404 (8) | C22—H22 | 0.93 |
C8—H8 | 0.93 | C23—C24 | 1.361 (9) |
C9—C10 | 1.409 (9) | C23—H23 | 0.93 |
C11—C12 | 1.419 (8) | C24—C25 | 1.382 (8) |
C13—H13A | 0.96 | C24—H24 | 0.93 |
C13—H13B | 0.96 | C25—C26 | 1.384 (8) |
C13—H13C | 0.96 | C25—H25 | 0.93 |
C14—C15 | 1.389 (8) | C26—H26 | 0.93 |
| | | |
C9—O1—C2 | 106.6 (5) | C19—C14—C3 | 120.4 (6) |
C3—C2—O1 | 111.5 (5) | C16—C15—C14 | 121.0 (6) |
C3—C2—C13 | 134.9 (6) | C16—C15—H15 | 119.5 |
O1—C2—C13 | 113.5 (6) | C14—C15—H15 | 119.5 |
C2—C3—C10 | 106.2 (5) | C15—C16—C17 | 121.0 (6) |
C2—C3—C14 | 127.1 (6) | C15—C16—H16 | 119.5 |
C10—C3—C14 | 126.7 (6) | C17—C16—H16 | 119.5 |
C11—C4—C10 | 115.4 (5) | C18—C17—C16 | 118.4 (6) |
C11—C4—H4 | 122.3 | C18—C17—H17 | 120.8 |
C10—C4—H4 | 122.3 | C16—C17—H17 | 120.8 |
C11—O5—C6 | 106.8 (4) | C17—C18—C19 | 121.0 (6) |
C7—C6—O5 | 112.0 (5) | C17—C18—H18 | 119.5 |
C7—C6—C20 | 133.5 (6) | C19—C18—H18 | 119.5 |
O5—C6—C20 | 114.5 (5) | C18—C19—C14 | 120.8 (6) |
C6—C7—C12 | 106.8 (5) | C18—C19—H19 | 119.6 |
C6—C7—C21 | 127.6 (6) | C14—C19—H19 | 119.6 |
C12—C7—C21 | 125.6 (6) | C6—C20—H20A | 109.5 |
C9—C8—C12 | 115.0 (5) | C6—C20—H20B | 109.5 |
C9—C8—H8 | 122.5 | H20A—C20—H20B | 109.5 |
C12—C8—H8 | 122.5 | C6—C20—H20C | 109.5 |
C8—C9—O1 | 124.4 (5) | H20A—C20—H20C | 109.5 |
C8—C9—C10 | 126.1 (6) | H20B—C20—H20C | 109.5 |
O1—C9—C10 | 109.5 (5) | C22—C21—C26 | 117.8 (5) |
C4—C10—C9 | 119.0 (5) | C22—C21—C7 | 122.2 (6) |
C4—C10—C3 | 134.8 (6) | C26—C21—C7 | 120.0 (5) |
C9—C10—C3 | 106.2 (5) | C21—C22—C23 | 121.2 (6) |
C4—C11—O5 | 125.2 (5) | C21—C22—H22 | 119.4 |
C4—C11—C12 | 125.4 (5) | C23—C22—H22 | 119.4 |
O5—C11—C12 | 109.4 (5) | C24—C23—C22 | 120.2 (6) |
C8—C12—C11 | 119.1 (5) | C24—C23—H23 | 119.9 |
C8—C12—C7 | 135.9 (5) | C22—C23—H23 | 119.9 |
C11—C12—C7 | 105.0 (5) | C23—C24—C25 | 119.4 (6) |
C2—C13—H13A | 109.5 | C23—C24—H24 | 120.3 |
C2—C13—H13B | 109.5 | C25—C24—H24 | 120.3 |
H13A—C13—H13B | 109.5 | C24—C25—C26 | 121.0 (6) |
C2—C13—H13C | 109.5 | C24—C25—H25 | 119.5 |
H13A—C13—H13C | 109.5 | C26—C25—H25 | 119.5 |
H13B—C13—H13C | 109.5 | C25—C26—C21 | 120.4 (6) |
C15—C14—C19 | 117.8 (6) | C25—C26—H26 | 119.8 |
C15—C14—C3 | 121.8 (6) | C21—C26—H26 | 119.8 |
| | | |
C9—O1—C2—C3 | −0.2 (7) | C4—C11—C12—C8 | −1.1 (10) |
C9—O1—C2—C13 | 179.6 (5) | O5—C11—C12—C8 | 178.4 (5) |
O1—C2—C3—C10 | 0.1 (8) | C4—C11—C12—C7 | −179.7 (6) |
C13—C2—C3—C10 | −179.6 (7) | O5—C11—C12—C7 | −0.2 (7) |
O1—C2—C3—C14 | 179.4 (6) | C6—C7—C12—C8 | −178.3 (7) |
C13—C2—C3—C14 | −0.3 (13) | C21—C7—C12—C8 | 0.3 (12) |
C11—O5—C6—C7 | −0.5 (7) | C6—C7—C12—C11 | −0.1 (7) |
C11—O5—C6—C20 | 178.2 (5) | C21—C7—C12—C11 | 178.5 (6) |
O5—C6—C7—C12 | 0.3 (8) | C2—C3—C14—C15 | 41.8 (10) |
C20—C6—C7—C12 | −178.0 (7) | C10—C3—C14—C15 | −139.0 (6) |
O5—C6—C7—C21 | −178.2 (6) | C2—C3—C14—C19 | −139.1 (7) |
C20—C6—C7—C21 | 3.5 (13) | C10—C3—C14—C19 | 40.1 (10) |
C12—C8—C9—O1 | 179.9 (6) | C19—C14—C15—C16 | −0.3 (9) |
C12—C8—C9—C10 | 0.0 (10) | C3—C14—C15—C16 | 178.8 (6) |
C2—O1—C9—C8 | −179.7 (7) | C14—C15—C16—C17 | −0.4 (11) |
C2—O1—C9—C10 | 0.2 (7) | C15—C16—C17—C18 | 0.6 (10) |
C11—C4—C10—C9 | 1.5 (8) | C16—C17—C18—C19 | −0.2 (10) |
C11—C4—C10—C3 | 179.9 (7) | C17—C18—C19—C14 | −0.5 (10) |
C8—C9—C10—C4 | −1.4 (11) | C15—C14—C19—C18 | 0.8 (9) |
O1—C9—C10—C4 | 178.7 (5) | C3—C14—C19—C18 | −178.4 (6) |
C8—C9—C10—C3 | 179.8 (6) | C6—C7—C21—C22 | 37.1 (10) |
O1—C9—C10—C3 | −0.1 (7) | C12—C7—C21—C22 | −141.2 (6) |
C2—C3—C10—C4 | −178.5 (7) | C6—C7—C21—C26 | −143.6 (7) |
C14—C3—C10—C4 | 2.1 (12) | C12—C7—C21—C26 | 38.1 (9) |
C2—C3—C10—C9 | 0.1 (8) | C26—C21—C22—C23 | −0.4 (9) |
C14—C3—C10—C9 | −179.3 (6) | C7—C21—C22—C23 | 178.8 (6) |
C10—C4—C11—O5 | −179.7 (6) | C21—C22—C23—C24 | −0.2 (10) |
C10—C4—C11—C12 | −0.3 (9) | C22—C23—C24—C25 | 0.0 (10) |
C6—O5—C11—C4 | 179.9 (6) | C23—C24—C25—C26 | 0.7 (10) |
C6—O5—C11—C12 | 0.4 (6) | C24—C25—C26—C21 | −1.4 (10) |
C9—C8—C12—C11 | 1.2 (8) | C22—C21—C26—C25 | 1.2 (9) |
C9—C8—C12—C7 | 179.2 (7) | C7—C21—C26—C25 | −178.1 (6) |