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The molecule of the title compound, C
50H
36O
8, lies on an inversion centre. Intermolecular C—H
O hydrogen bonds result in the formation of an intricate three-dimensional network.
Supporting information
CCDC reference: 606676
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.065
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 33 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for C17 - C18 .. 7.55 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for C24 - C25 .. 7.81 su
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.762
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.114
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
4 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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
C50H36O8 | F(000) = 800 |
Mr = 764.79 | Dx = 1.396 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1046 reflections |
a = 7.598 (2) Å | θ = 2.0–25.0° |
b = 19.448 (5) Å | µ = 0.09 mm−1 |
c = 12.541 (3) Å | T = 173 K |
β = 100.896 (6)° | Prism, colorless |
V = 1819.7 (8) Å3 | 0.45 × 0.35 × 0.25 mm |
Z = 2 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1046 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.114 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
φ and ω scans | h = −9→7 |
9367 measured reflections | k = −23→20 |
3190 independent reflections | l = −14→14 |
Refinement top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H-atom parameters constrained |
S = 0.76 | w = 1/[σ2(Fo2) + (0.0042P)2] where P = (Fo2 + 2Fc2)/3 |
3190 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
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. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O3 | 0.2307 (3) | −0.00234 (10) | 0.70255 (16) | 0.0557 (6) | |
O2 | −0.1370 (3) | 0.12673 (11) | 0.54371 (16) | 0.0653 (7) | |
O4 | 0.7292 (3) | 0.04863 (12) | 0.79148 (17) | 0.0733 (7) | |
O1 | −0.6319 (3) | 0.07826 (13) | 0.4297 (2) | 0.0946 (9) | |
C23 | 0.5866 (4) | −0.06138 (15) | 0.9215 (2) | 0.0416 (8) | |
C8 | −0.3666 (4) | 0.23894 (17) | 0.2711 (3) | 0.0513 (9) | |
C24 | 0.4916 (4) | −0.02386 (15) | 0.8296 (2) | 0.0365 (8) | |
C15 | 0.3103 (4) | −0.03642 (15) | 0.7936 (2) | 0.0408 (8) | |
C18 | 0.4914 (4) | −0.10888 (16) | 0.9742 (3) | 0.0429 (9) | |
C2 | −0.3869 (4) | 0.14881 (16) | 0.4047 (3) | 0.0454 (8) | |
C11 | −0.2084 (5) | 0.16110 (16) | 0.4502 (3) | 0.0470 (9) | |
C16 | 0.2163 (4) | −0.08291 (15) | 0.8477 (2) | 0.0498 (9) | |
H16 | 0.0941 | −0.0899 | 0.8239 | 0.060* | |
C19 | 0.5804 (5) | −0.14616 (16) | 1.0647 (2) | 0.0583 (10) | |
H19 | 0.5162 | −0.1767 | 1.0998 | 0.070* | |
C10 | −0.1085 (4) | 0.21114 (16) | 0.4084 (2) | 0.0593 (10) | |
H10 | 0.0099 | 0.2191 | 0.4415 | 0.071* | |
C22 | 0.7722 (4) | −0.05430 (15) | 0.9618 (2) | 0.0509 (9) | |
H22 | 0.8387 | −0.0236 | 0.9286 | 0.061* | |
C6 | −0.6193 (6) | 0.27144 (19) | 0.1346 (3) | 0.0775 (12) | |
H6 | −0.6702 | 0.2983 | 0.0754 | 0.093* | |
C7 | −0.4428 (5) | 0.27938 (16) | 0.1802 (3) | 0.0653 (11) | |
H7 | −0.3728 | 0.3112 | 0.1517 | 0.078* | |
C3 | −0.4704 (4) | 0.18975 (16) | 0.3133 (2) | 0.0457 (9) | |
C9 | −0.1841 (4) | 0.24849 (15) | 0.3188 (3) | 0.0589 (10) | |
H9 | −0.1152 | 0.2802 | 0.2893 | 0.071* | |
C17 | 0.3065 (5) | −0.11778 (15) | 0.9356 (3) | 0.0537 (9) | |
H17 | 0.2437 | −0.1485 | 0.9712 | 0.064* | |
C5 | −0.7234 (5) | 0.2232 (2) | 0.1767 (3) | 0.0757 (13) | |
H5 | −0.8433 | 0.2180 | 0.1443 | 0.091* | |
C4 | −0.6541 (4) | 0.18308 (18) | 0.2645 (3) | 0.0650 (11) | |
H4 | −0.7268 | 0.1518 | 0.2919 | 0.078* | |
C21 | 0.8560 (4) | −0.09208 (17) | 1.0492 (3) | 0.0598 (10) | |
H21 | 0.9786 | −0.0870 | 1.0741 | 0.072* | |
C20 | 0.7594 (5) | −0.13795 (18) | 1.1011 (3) | 0.0669 (11) | |
H20 | 0.8173 | −0.1630 | 1.1607 | 0.080* | |
C13 | 0.0161 (4) | 0.01804 (17) | 0.5461 (2) | 0.0463 (9) | |
C14 | 0.0442 (4) | −0.01548 (15) | 0.6570 (2) | 0.0541 (9) | |
H14A | −0.0334 | 0.0049 | 0.7015 | 0.065* | |
H14B | 0.0207 | −0.0645 | 0.6507 | 0.065* | |
C12 | 0.0364 (4) | 0.09585 (16) | 0.5510 (2) | 0.0574 (9) | |
H12A | 0.1134 | 0.1091 | 0.6187 | 0.069* | |
H12B | 0.0911 | 0.1117 | 0.4916 | 0.069* | |
C25 | 0.5753 (4) | 0.02883 (16) | 0.7731 (2) | 0.0557 (10) | |
H25 | 0.5005 | 0.0501 | 0.7152 | 0.067* | |
C1 | −0.4752 (5) | 0.09216 (17) | 0.4496 (3) | 0.0645 (11) | |
H1 | −0.4024 | 0.0638 | 0.4990 | 0.077* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3 | 0.0441 (15) | 0.0649 (17) | 0.0509 (15) | −0.0067 (11) | −0.0096 (13) | 0.0141 (12) |
O2 | 0.0626 (17) | 0.0771 (19) | 0.0547 (16) | 0.0223 (13) | 0.0070 (14) | 0.0113 (14) |
O4 | 0.0480 (16) | 0.093 (2) | 0.0741 (18) | −0.0142 (14) | −0.0017 (14) | 0.0230 (14) |
O1 | 0.0617 (18) | 0.095 (2) | 0.131 (2) | −0.0146 (15) | 0.0281 (19) | 0.0172 (17) |
C23 | 0.045 (2) | 0.040 (2) | 0.038 (2) | 0.0052 (18) | 0.0066 (19) | −0.0055 (17) |
C8 | 0.054 (3) | 0.047 (3) | 0.052 (3) | 0.007 (2) | 0.007 (2) | −0.0025 (19) |
C24 | 0.034 (2) | 0.042 (2) | 0.035 (2) | 0.0007 (16) | 0.0098 (18) | 0.0017 (17) |
C15 | 0.044 (2) | 0.043 (2) | 0.036 (2) | 0.0051 (17) | 0.008 (2) | 0.0012 (17) |
C18 | 0.043 (2) | 0.042 (2) | 0.043 (2) | 0.0059 (17) | 0.006 (2) | −0.0001 (17) |
C2 | 0.044 (2) | 0.044 (2) | 0.051 (2) | −0.0021 (18) | 0.014 (2) | −0.0059 (19) |
C11 | 0.054 (3) | 0.043 (2) | 0.044 (2) | 0.0035 (18) | 0.010 (2) | 0.0044 (18) |
C16 | 0.043 (2) | 0.057 (2) | 0.049 (2) | −0.0070 (18) | 0.0062 (19) | 0.0000 (19) |
C19 | 0.068 (3) | 0.050 (2) | 0.057 (3) | 0.009 (2) | 0.011 (2) | 0.013 (2) |
C10 | 0.054 (2) | 0.059 (3) | 0.060 (3) | −0.006 (2) | −0.004 (2) | −0.001 (2) |
C22 | 0.053 (2) | 0.050 (2) | 0.047 (2) | 0.0019 (18) | 0.002 (2) | 0.0021 (19) |
C6 | 0.088 (3) | 0.073 (3) | 0.064 (3) | 0.029 (3) | −0.003 (3) | −0.002 (2) |
C7 | 0.078 (3) | 0.054 (3) | 0.061 (3) | 0.017 (2) | 0.007 (2) | 0.000 (2) |
C3 | 0.044 (2) | 0.043 (2) | 0.048 (2) | 0.0053 (18) | 0.004 (2) | −0.0137 (19) |
C9 | 0.056 (3) | 0.055 (3) | 0.066 (3) | −0.0092 (19) | 0.014 (2) | 0.006 (2) |
C17 | 0.068 (3) | 0.042 (2) | 0.055 (3) | −0.0028 (18) | 0.019 (2) | 0.0043 (18) |
C5 | 0.061 (3) | 0.079 (3) | 0.076 (3) | 0.021 (2) | −0.014 (3) | −0.016 (2) |
C4 | 0.053 (3) | 0.061 (3) | 0.080 (3) | 0.003 (2) | 0.008 (2) | −0.015 (2) |
C21 | 0.049 (2) | 0.066 (3) | 0.059 (3) | 0.007 (2) | −0.005 (2) | 0.001 (2) |
C20 | 0.074 (3) | 0.066 (3) | 0.057 (3) | 0.022 (2) | 0.001 (2) | 0.013 (2) |
C13 | 0.0291 (18) | 0.056 (3) | 0.051 (3) | 0.0020 (16) | −0.0015 (19) | −0.0035 (18) |
C14 | 0.040 (2) | 0.063 (2) | 0.055 (2) | 0.0008 (17) | −0.0022 (19) | −0.0013 (19) |
C12 | 0.047 (2) | 0.056 (3) | 0.061 (2) | −0.0008 (18) | −0.0109 (19) | −0.0035 (19) |
C25 | 0.045 (2) | 0.071 (3) | 0.046 (2) | −0.001 (2) | −0.003 (2) | 0.0062 (19) |
C1 | 0.063 (3) | 0.056 (3) | 0.080 (3) | 0.001 (2) | 0.026 (3) | −0.001 (2) |
Geometric parameters (Å, º) top
O3—C15 | 1.359 (3) | C10—H10 | 0.9300 |
O3—C14 | 1.447 (3) | C22—C21 | 1.373 (3) |
O2—C11 | 1.369 (3) | C22—H22 | 0.9300 |
O2—C12 | 1.435 (3) | C6—C7 | 1.363 (4) |
O4—C25 | 1.211 (3) | C6—C5 | 1.394 (4) |
O1—C1 | 1.200 (3) | C6—H6 | 0.9300 |
C23—C18 | 1.412 (4) | C7—H7 | 0.9300 |
C23—C22 | 1.412 (3) | C3—C4 | 1.420 (4) |
C23—C24 | 1.438 (3) | C9—H9 | 0.9300 |
C8—C3 | 1.405 (4) | C17—H17 | 0.9300 |
C8—C9 | 1.415 (4) | C5—C4 | 1.371 (4) |
C8—C7 | 1.416 (4) | C5—H5 | 0.9300 |
C24—C15 | 1.388 (3) | C4—H4 | 0.9300 |
C24—C25 | 1.458 (4) | C21—C20 | 1.393 (4) |
C15—C16 | 1.404 (3) | C21—H21 | 0.9300 |
C18—C19 | 1.407 (4) | C20—H20 | 0.9300 |
C18—C17 | 1.407 (4) | C13—C13i | 1.335 (5) |
C2—C11 | 1.389 (4) | C13—C14 | 1.514 (4) |
C2—C3 | 1.440 (4) | C13—C12 | 1.521 (4) |
C2—C1 | 1.458 (4) | C14—H14A | 0.9700 |
C11—C10 | 1.396 (4) | C14—H14B | 0.9700 |
C16—C17 | 1.363 (3) | C12—H12A | 0.9700 |
C16—H16 | 0.9300 | C12—H12B | 0.9700 |
C19—C20 | 1.360 (4) | C25—H25 | 0.9300 |
C19—H19 | 0.9300 | C1—H1 | 0.9300 |
C10—C9 | 1.369 (4) | | |
| | | |
C15—O3—C14 | 119.5 (2) | C8—C3—C2 | 118.8 (3) |
C11—O2—C12 | 118.0 (2) | C4—C3—C2 | 122.8 (3) |
C18—C23—C22 | 117.5 (3) | C10—C9—C8 | 120.2 (3) |
C18—C23—C24 | 118.9 (3) | C10—C9—H9 | 119.9 |
C22—C23—C24 | 123.6 (3) | C8—C9—H9 | 119.9 |
C3—C8—C9 | 120.4 (3) | C16—C17—C18 | 122.2 (3) |
C3—C8—C7 | 120.5 (3) | C16—C17—H17 | 118.9 |
C9—C8—C7 | 119.1 (4) | C18—C17—H17 | 118.9 |
C15—C24—C23 | 119.2 (3) | C4—C5—C6 | 121.8 (4) |
C15—C24—C25 | 117.6 (3) | C4—C5—H5 | 119.1 |
C23—C24—C25 | 123.2 (3) | C6—C5—H5 | 119.1 |
O3—C15—C24 | 116.4 (3) | C5—C4—C3 | 119.4 (3) |
O3—C15—C16 | 122.3 (3) | C5—C4—H4 | 120.3 |
C24—C15—C16 | 121.3 (3) | C3—C4—H4 | 120.3 |
C19—C18—C17 | 120.7 (3) | C22—C21—C20 | 120.7 (3) |
C19—C18—C23 | 120.3 (3) | C22—C21—H21 | 119.7 |
C17—C18—C23 | 119.1 (3) | C20—C21—H21 | 119.7 |
C11—C2—C3 | 118.8 (3) | C19—C20—C21 | 120.0 (3) |
C11—C2—C1 | 117.1 (3) | C19—C20—H20 | 120.0 |
C3—C2—C1 | 124.0 (3) | C21—C20—H20 | 120.0 |
O2—C11—C2 | 117.8 (3) | C13i—C13—C14 | 122.7 (4) |
O2—C11—C10 | 120.5 (3) | C13i—C13—C12 | 124.0 (4) |
C2—C11—C10 | 121.5 (3) | C14—C13—C12 | 113.3 (2) |
C17—C16—C15 | 119.2 (3) | O3—C14—C13 | 104.2 (2) |
C17—C16—H16 | 120.4 | O3—C14—H14A | 110.9 |
C15—C16—H16 | 120.4 | C13—C14—H14A | 110.9 |
C20—C19—C18 | 120.5 (3) | O3—C14—H14B | 110.9 |
C20—C19—H19 | 119.7 | C13—C14—H14B | 110.9 |
C18—C19—H19 | 119.7 | H14A—C14—H14B | 108.9 |
C9—C10—C11 | 120.3 (3) | O2—C12—C13 | 109.2 (2) |
C9—C10—H10 | 119.8 | O2—C12—H12A | 109.8 |
C11—C10—H10 | 119.8 | C13—C12—H12A | 109.8 |
C21—C22—C23 | 121.0 (3) | O2—C12—H12B | 109.8 |
C21—C22—H22 | 119.5 | C13—C12—H12B | 109.8 |
C23—C22—H22 | 119.5 | H12A—C12—H12B | 108.3 |
C7—C6—C5 | 120.1 (4) | O4—C25—C24 | 128.7 (3) |
C7—C6—H6 | 120.0 | O4—C25—H25 | 115.7 |
C5—C6—H6 | 120.0 | C24—C25—H25 | 115.7 |
C6—C7—C8 | 119.6 (4) | O1—C1—C2 | 126.9 (4) |
C6—C7—H7 | 120.2 | O1—C1—H1 | 116.5 |
C8—C7—H7 | 120.2 | C2—C1—H1 | 116.5 |
C8—C3—C4 | 118.4 (3) | | |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14A···O4ii | 0.97 | 2.45 | 3.414 (4) | 171 |
C12—H12B···O1iii | 0.97 | 2.46 | 3.199 (4) | 132 |
Symmetry codes: (ii) x−1, y, z; (iii) x+1, y, z. |
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