organic compounds
Dibenzo[b,g]indeno[1′,2′:3,4]fluoreno[1,2-d]oxonine-5,11,16,21-tetraone
aChemistry Department, Faculty of Science, Minia University, Egypt, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt
*Correspondence e-mail: akkurt@erciyes.edu.tr, dmntahir_uos@yahoo.com
The 34H16O5, contains two independent molecules (A and B) with similar conformations. The two benzene rings attached to the nine-membered ring are inclined to one another at 63.62 (14)° in molecule A and 68.23 (12)° in molecule B. One intramoleculer C—H⋯O hydrogen bond occurs in molecule A and two are observed in molecule B. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming a three-dimensional network structure with R22(10) and R22(24) ring motifs. Aromatic π–π stacking interactions [centroid–centroid distances = 3.7572 (19), 3.6996 (19) and 3.7043 (19) Å] are also observed. The contains a pair of voids of 37 (2) Å3 about an inversion centre but the residual electron density (highest peak = 0.19 e Å−3 and deepest hole = −0.20 e Å−3) in the difference Fourier map suggests that no solvent molecule occupies this void.
of the title compound, CRelated literature
1,3-Indandione undergoes self-condensation quite easily, see: Zargar & Khan (2012). For industrial and biological applications of indandion containing compounds see: Seniutinas et al. (2012); Jin et al. (2009). For ring conformations, see: Cremer & Pople (1975).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
10.1107/S1600536812046363/xu5643sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812046363/xu5643Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812046363/xu5643Isup3.cml
The title compound was obtained from a reaction mixture of 4 mmol (576 mg) indandione and 2 mmol (244 mg) salicylaldehyde in presence of 1 mmol (90 mg) 1,3-diaminopropan-2-ol in 50 ml e thanol. The reaction mixture was refluxed for 6 h at 350 K. The excess solvent was evaporated under vacum and the obtained solid was recrystallized from acetic acid to afford a good yield (82%) of dark green crystals (m.p. 575 K) suitable for X-ray diffraction.
All H atoms were located geometrically and treated as riding atoms with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).Fig. 1. View of the molecule A of two molecules of (I) in the asymmetric unit. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. | |
Fig. 2. View of the molecule B of two molecules of (I) in the asymmetric unit. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. | |
Fig. 3. View of the molecular packing of (I) down the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity. |
C34H16O5 | Z = 4 |
Mr = 504.47 | F(000) = 1040 |
Triclinic, P1 | Dx = 1.406 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.230 (4) Å | Cell parameters from 182 reflections |
b = 12.346 (3) Å | θ = 3.3–21.5° |
c = 16.794 (5) Å | µ = 0.10 mm−1 |
α = 82.229 (7)° | T = 296 K |
β = 72.773 (6)° | Prism, dark green |
γ = 81.181 (10)° | 0.28 × 0.18 × 0.14 mm |
V = 2382.5 (12) Å3 |
Bruker Kappa APEXII CCD diffractometer | 10895 independent reflections |
Radiation source: fine-focus sealed tube | 4858 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
Detector resolution: 0.81 pixels mm-1 | θmax = 27.6°, θmin = 2.3° |
ω scans | h = −15→15 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −16→16 |
Tmin = 0.980, Tmax = 0.987 | l = −21→21 |
38137 measured 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)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0501P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
10895 reflections | Δρmax = 0.19 e Å−3 |
704 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0020 (4) |
C34H16O5 | γ = 81.181 (10)° |
Mr = 504.47 | V = 2382.5 (12) Å3 |
Triclinic, P1 | Z = 4 |
a = 12.230 (4) Å | Mo Kα radiation |
b = 12.346 (3) Å | µ = 0.10 mm−1 |
c = 16.794 (5) Å | T = 296 K |
α = 82.229 (7)° | 0.28 × 0.18 × 0.14 mm |
β = 72.773 (6)° |
Bruker Kappa APEXII CCD diffractometer | 10895 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 4858 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.987 | Rint = 0.061 |
38137 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.19 e Å−3 |
10895 reflections | Δρmin = −0.21 e Å−3 |
704 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | 0.30343 (13) | 0.59668 (14) | 0.68545 (12) | 0.0606 (7) | |
O2 | 0.36189 (17) | 0.52360 (19) | 0.56612 (14) | 0.0919 (10) | |
O3 | 0.65201 (14) | 0.36139 (15) | 0.71664 (13) | 0.0755 (8) | |
O4 | 0.31239 (15) | 0.02705 (15) | 0.72691 (12) | 0.0721 (8) | |
O5 | 0.12537 (14) | 0.48837 (16) | 0.91275 (12) | 0.0710 (8) | |
C1 | 0.36124 (18) | 0.5327 (2) | 0.80850 (17) | 0.0457 (9) | |
C2 | 0.3815 (2) | 0.5551 (3) | 0.88099 (18) | 0.0660 (11) | |
C3 | 0.3712 (2) | 0.6644 (3) | 0.8990 (2) | 0.0826 (16) | |
C4 | 0.3414 (2) | 0.7490 (3) | 0.8436 (3) | 0.0847 (16) | |
C5 | 0.3211 (2) | 0.7288 (2) | 0.7722 (2) | 0.0709 (13) | |
C6 | 0.33166 (19) | 0.6210 (2) | 0.75593 (17) | 0.0495 (10) | |
C7 | 0.3894 (2) | 0.5616 (2) | 0.61735 (19) | 0.0570 (11) | |
C8 | 0.5070 (2) | 0.5881 (2) | 0.61130 (15) | 0.0474 (9) | |
C9 | 0.5342 (3) | 0.6868 (2) | 0.56465 (18) | 0.0692 (12) | |
C10 | 0.6393 (3) | 0.7211 (3) | 0.5530 (2) | 0.0821 (14) | |
C11 | 0.7199 (3) | 0.6572 (3) | 0.5856 (2) | 0.0797 (15) | |
C12 | 0.6954 (2) | 0.5587 (2) | 0.63184 (18) | 0.0616 (11) | |
C13 | 0.58751 (19) | 0.5234 (2) | 0.64604 (15) | 0.0431 (9) | |
C14 | 0.57028 (19) | 0.4167 (2) | 0.69716 (16) | 0.0462 (9) | |
C15 | 0.45753 (17) | 0.36805 (19) | 0.72787 (14) | 0.0400 (9) | |
C16 | 0.36222 (19) | 0.41890 (19) | 0.78720 (15) | 0.0422 (9) | |
C17 | 0.26743 (18) | 0.3624 (2) | 0.82399 (14) | 0.0415 (9) | |
C18 | 0.26223 (18) | 0.2556 (2) | 0.80507 (14) | 0.0407 (8) | |
C19 | 0.35423 (18) | 0.20753 (19) | 0.74519 (14) | 0.0403 (8) | |
C20 | 0.45172 (18) | 0.2643 (2) | 0.70666 (15) | 0.0416 (9) | |
C21 | 0.53516 (18) | 0.1954 (2) | 0.64342 (15) | 0.0445 (9) | |
C22 | 0.6417 (2) | 0.2118 (2) | 0.58698 (17) | 0.0609 (10) | |
C23 | 0.6949 (2) | 0.1317 (2) | 0.53227 (18) | 0.0672 (11) | |
C24 | 0.6467 (2) | 0.0389 (2) | 0.53273 (18) | 0.0659 (11) | |
C25 | 0.5414 (2) | 0.0214 (2) | 0.58938 (17) | 0.0585 (10) | |
C26 | 0.48748 (19) | 0.1004 (2) | 0.64358 (15) | 0.0449 (9) | |
C27 | 0.3741 (2) | 0.0999 (2) | 0.70820 (16) | 0.0482 (10) | |
C28 | 0.1557 (2) | 0.3987 (2) | 0.88562 (16) | 0.0477 (9) | |
C29 | 0.08788 (19) | 0.3041 (2) | 0.90507 (15) | 0.0456 (9) | |
C30 | −0.02000 (19) | 0.2945 (2) | 0.95961 (16) | 0.0532 (10) | |
C31 | −0.0662 (2) | 0.1982 (2) | 0.96602 (17) | 0.0588 (10) | |
C32 | −0.0065 (2) | 0.1132 (2) | 0.91909 (16) | 0.0556 (10) | |
C33 | 0.10298 (19) | 0.1220 (2) | 0.86364 (15) | 0.0503 (9) | |
C34 | 0.15016 (18) | 0.2189 (2) | 0.85727 (15) | 0.0417 (9) | |
O6 | 1.00908 (13) | −0.17362 (14) | 0.77863 (11) | 0.0535 (7) | |
O7 | 0.90062 (15) | −0.12612 (16) | 0.90231 (12) | 0.0674 (8) | |
O8 | 0.63534 (16) | −0.13362 (14) | 0.72125 (13) | 0.0714 (8) | |
O9 | 0.68213 (15) | 0.30354 (15) | 0.88768 (11) | 0.0639 (7) | |
O10 | 1.11392 (14) | 0.04935 (15) | 0.60688 (12) | 0.0679 (7) | |
C35 | 0.94112 (18) | −0.11759 (19) | 0.65889 (16) | 0.0419 (9) | |
C36 | 0.9417 (2) | −0.1352 (2) | 0.57890 (17) | 0.0529 (10) | |
C37 | 1.0053 (2) | −0.2271 (2) | 0.54203 (17) | 0.0577 (10) | |
C38 | 1.0671 (2) | −0.3024 (2) | 0.5844 (2) | 0.0609 (10) | |
C39 | 1.06743 (19) | −0.2873 (2) | 0.66449 (19) | 0.0557 (10) | |
C40 | 1.00473 (18) | −0.1955 (2) | 0.69976 (16) | 0.0433 (9) | |
C41 | 0.9114 (2) | −0.1772 (2) | 0.84396 (18) | 0.0483 (10) | |
C42 | 0.83080 (18) | −0.25756 (19) | 0.84404 (15) | 0.0409 (8) | |
C43 | 0.8502 (2) | −0.3585 (2) | 0.88940 (15) | 0.0504 (10) | |
C44 | 0.7807 (2) | −0.4394 (2) | 0.89913 (17) | 0.0586 (11) | |
C45 | 0.6915 (2) | −0.4225 (2) | 0.86307 (17) | 0.0573 (10) | |
C46 | 0.67236 (19) | −0.3245 (2) | 0.81736 (16) | 0.0498 (10) | |
C47 | 0.74017 (18) | −0.23984 (19) | 0.80699 (14) | 0.0389 (8) | |
C48 | 0.70772 (19) | −0.1365 (2) | 0.75803 (16) | 0.0453 (9) | |
C49 | 0.76039 (18) | −0.03298 (19) | 0.75539 (15) | 0.0407 (8) | |
C50 | 0.87355 (18) | −0.02196 (19) | 0.70404 (14) | 0.0408 (8) | |
C51 | 0.91980 (18) | 0.0738 (2) | 0.70171 (14) | 0.0411 (8) | |
C52 | 0.85951 (18) | 0.16119 (19) | 0.74945 (14) | 0.0391 (8) | |
C53 | 0.74977 (18) | 0.14884 (18) | 0.80130 (14) | 0.0384 (8) | |
C54 | 0.69851 (18) | 0.05350 (19) | 0.80181 (14) | 0.0383 (8) | |
C55 | 0.57903 (18) | 0.0654 (2) | 0.85817 (15) | 0.0416 (8) | |
C56 | 0.49093 (19) | −0.0013 (2) | 0.87878 (16) | 0.0531 (10) | |
C57 | 0.3861 (2) | 0.0352 (2) | 0.93379 (17) | 0.0606 (11) | |
C58 | 0.3681 (2) | 0.1337 (3) | 0.96666 (17) | 0.0616 (10) | |
C59 | 0.4552 (2) | 0.2002 (2) | 0.94781 (15) | 0.0542 (10) | |
C60 | 0.55958 (19) | 0.1651 (2) | 0.89297 (15) | 0.0433 (9) | |
C61 | 0.66597 (19) | 0.2206 (2) | 0.86300 (15) | 0.0443 (9) | |
C62 | 1.0373 (2) | 0.1048 (2) | 0.65342 (16) | 0.0490 (10) | |
C63 | 1.03846 (19) | 0.2175 (2) | 0.67471 (15) | 0.0456 (9) | |
C64 | 1.1243 (2) | 0.2854 (2) | 0.64486 (16) | 0.0558 (10) | |
C65 | 1.1039 (2) | 0.3894 (3) | 0.67096 (18) | 0.0656 (11) | |
C66 | 0.9996 (2) | 0.4235 (2) | 0.72629 (18) | 0.0645 (11) | |
C67 | 0.9133 (2) | 0.3553 (2) | 0.75702 (16) | 0.0538 (10) | |
C68 | 0.93334 (19) | 0.2515 (2) | 0.73056 (15) | 0.0418 (9) | |
H2 | 0.40190 | 0.49770 | 0.91780 | 0.0790* | |
H3 | 0.38440 | 0.68000 | 0.94780 | 0.0990* | |
H4 | 0.33520 | 0.82140 | 0.85550 | 0.1020* | |
H5 | 0.30060 | 0.78610 | 0.73540 | 0.0850* | |
H9 | 0.48030 | 0.73010 | 0.54110 | 0.0830* | |
H10 | 0.65600 | 0.78820 | 0.52260 | 0.0980* | |
H11 | 0.79180 | 0.68040 | 0.57660 | 0.0960* | |
H12 | 0.75090 | 0.51540 | 0.65370 | 0.0740* | |
H22 | 0.67620 | 0.27430 | 0.58580 | 0.0730* | |
H23 | 0.76600 | 0.14180 | 0.49400 | 0.0810* | |
H24 | 0.68460 | −0.01250 | 0.49500 | 0.0790* | |
H25 | 0.50800 | −0.04180 | 0.59090 | 0.0700* | |
H30 | −0.06040 | 0.35170 | 0.99120 | 0.0640* | |
H31 | −0.13900 | 0.19010 | 1.00250 | 0.0710* | |
H32 | −0.03970 | 0.04870 | 0.92450 | 0.0670* | |
H33 | 0.14290 | 0.06460 | 0.83200 | 0.0600* | |
H36 | 0.89900 | −0.08480 | 0.54990 | 0.0630* | |
H37 | 1.00590 | −0.23780 | 0.48810 | 0.0690* | |
H38 | 1.10920 | −0.36430 | 0.55920 | 0.0730* | |
H39 | 1.10930 | −0.33840 | 0.69360 | 0.0670* | |
H43 | 0.91110 | −0.37100 | 0.91330 | 0.0610* | |
H44 | 0.79390 | −0.50580 | 0.93020 | 0.0700* | |
H45 | 0.64430 | −0.47730 | 0.86970 | 0.0690* | |
H46 | 0.61240 | −0.31420 | 0.79250 | 0.0600* | |
H56 | 0.50180 | −0.06840 | 0.85640 | 0.0640* | |
H57 | 0.32650 | −0.00880 | 0.94860 | 0.0730* | |
H58 | 0.29630 | 0.15630 | 1.00220 | 0.0740* | |
H59 | 0.44400 | 0.26650 | 0.97130 | 0.0650* | |
H64 | 1.19450 | 0.26140 | 0.60790 | 0.0670* | |
H65 | 1.16040 | 0.43670 | 0.65130 | 0.0790* | |
H66 | 0.98690 | 0.49400 | 0.74340 | 0.0770* | |
H67 | 0.84370 | 0.37910 | 0.79460 | 0.0650* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0502 (10) | 0.0595 (13) | 0.0732 (14) | 0.0036 (9) | −0.0241 (10) | −0.0066 (11) |
O2 | 0.0874 (15) | 0.120 (2) | 0.0876 (17) | −0.0121 (13) | −0.0433 (13) | −0.0343 (15) |
O3 | 0.0540 (11) | 0.0714 (14) | 0.1047 (17) | −0.0081 (10) | −0.0386 (11) | 0.0168 (12) |
O4 | 0.0663 (12) | 0.0524 (13) | 0.0930 (16) | −0.0217 (10) | −0.0010 (11) | −0.0229 (11) |
O5 | 0.0637 (11) | 0.0605 (14) | 0.0801 (15) | −0.0056 (10) | 0.0023 (10) | −0.0303 (12) |
C1 | 0.0398 (13) | 0.0489 (18) | 0.0484 (17) | −0.0110 (12) | −0.0061 (12) | −0.0121 (15) |
C2 | 0.0640 (17) | 0.079 (2) | 0.058 (2) | −0.0239 (16) | −0.0094 (15) | −0.0167 (18) |
C3 | 0.074 (2) | 0.108 (3) | 0.071 (3) | −0.039 (2) | 0.0024 (18) | −0.046 (2) |
C4 | 0.066 (2) | 0.070 (3) | 0.113 (3) | −0.0272 (18) | 0.009 (2) | −0.047 (3) |
C5 | 0.0593 (18) | 0.045 (2) | 0.103 (3) | −0.0059 (14) | −0.0089 (18) | −0.0208 (19) |
C6 | 0.0387 (13) | 0.0469 (19) | 0.060 (2) | −0.0056 (12) | −0.0047 (13) | −0.0153 (16) |
C7 | 0.0576 (17) | 0.0535 (19) | 0.060 (2) | 0.0011 (14) | −0.0209 (16) | −0.0051 (16) |
C8 | 0.0522 (15) | 0.0397 (17) | 0.0469 (17) | −0.0037 (13) | −0.0083 (13) | −0.0073 (14) |
C9 | 0.078 (2) | 0.052 (2) | 0.065 (2) | −0.0009 (16) | −0.0078 (17) | 0.0024 (17) |
C10 | 0.092 (2) | 0.048 (2) | 0.083 (3) | −0.0186 (19) | 0.014 (2) | −0.0023 (18) |
C11 | 0.0650 (19) | 0.076 (3) | 0.090 (3) | −0.0323 (18) | 0.0043 (18) | −0.012 (2) |
C12 | 0.0518 (16) | 0.063 (2) | 0.069 (2) | −0.0189 (14) | −0.0096 (14) | −0.0059 (17) |
C13 | 0.0436 (13) | 0.0426 (16) | 0.0430 (16) | −0.0102 (12) | −0.0084 (12) | −0.0071 (13) |
C14 | 0.0397 (13) | 0.0490 (17) | 0.0516 (17) | −0.0043 (12) | −0.0153 (12) | −0.0067 (14) |
C15 | 0.0401 (13) | 0.0363 (16) | 0.0442 (16) | −0.0060 (11) | −0.0122 (12) | −0.0037 (13) |
C16 | 0.0449 (13) | 0.0376 (16) | 0.0455 (16) | −0.0076 (11) | −0.0138 (12) | −0.0031 (13) |
C17 | 0.0419 (13) | 0.0399 (16) | 0.0440 (16) | −0.0050 (11) | −0.0125 (12) | −0.0079 (13) |
C18 | 0.0410 (13) | 0.0414 (16) | 0.0409 (15) | −0.0057 (11) | −0.0132 (12) | −0.0031 (13) |
C19 | 0.0428 (13) | 0.0373 (16) | 0.0404 (15) | −0.0049 (11) | −0.0105 (12) | −0.0054 (12) |
C20 | 0.0425 (13) | 0.0378 (16) | 0.0435 (16) | −0.0050 (11) | −0.0124 (12) | 0.0006 (13) |
C21 | 0.0409 (13) | 0.0420 (17) | 0.0479 (17) | −0.0008 (12) | −0.0112 (12) | −0.0022 (13) |
C22 | 0.0512 (15) | 0.0572 (19) | 0.066 (2) | −0.0088 (14) | −0.0021 (15) | −0.0073 (16) |
C23 | 0.0484 (15) | 0.066 (2) | 0.071 (2) | −0.0019 (15) | 0.0081 (15) | −0.0130 (18) |
C24 | 0.0563 (17) | 0.062 (2) | 0.065 (2) | 0.0077 (15) | 0.0011 (15) | −0.0147 (17) |
C25 | 0.0583 (16) | 0.0475 (18) | 0.067 (2) | 0.0006 (13) | −0.0134 (15) | −0.0134 (16) |
C26 | 0.0454 (13) | 0.0424 (17) | 0.0434 (16) | 0.0007 (12) | −0.0094 (12) | −0.0061 (13) |
C27 | 0.0484 (14) | 0.0433 (18) | 0.0525 (18) | −0.0041 (13) | −0.0125 (13) | −0.0087 (14) |
C28 | 0.0477 (14) | 0.0460 (18) | 0.0477 (17) | −0.0008 (13) | −0.0096 (12) | −0.0126 (14) |
C29 | 0.0430 (13) | 0.0502 (18) | 0.0448 (16) | −0.0072 (12) | −0.0126 (12) | −0.0059 (14) |
C30 | 0.0469 (15) | 0.062 (2) | 0.0496 (18) | −0.0067 (13) | −0.0094 (13) | −0.0110 (15) |
C31 | 0.0500 (15) | 0.071 (2) | 0.0520 (19) | −0.0132 (15) | −0.0069 (13) | −0.0040 (16) |
C32 | 0.0579 (16) | 0.059 (2) | 0.0522 (18) | −0.0233 (14) | −0.0149 (14) | 0.0039 (15) |
C33 | 0.0492 (14) | 0.0487 (18) | 0.0512 (17) | −0.0084 (13) | −0.0101 (13) | −0.0046 (14) |
C34 | 0.0432 (13) | 0.0412 (16) | 0.0413 (16) | −0.0084 (12) | −0.0123 (12) | −0.0014 (13) |
O6 | 0.0445 (10) | 0.0616 (13) | 0.0568 (12) | −0.0101 (8) | −0.0177 (9) | −0.0017 (10) |
O7 | 0.0801 (13) | 0.0696 (14) | 0.0628 (14) | −0.0236 (10) | −0.0230 (11) | −0.0188 (11) |
O8 | 0.0838 (13) | 0.0526 (13) | 0.0974 (16) | −0.0077 (10) | −0.0588 (12) | −0.0003 (11) |
O9 | 0.0766 (12) | 0.0522 (13) | 0.0598 (13) | −0.0122 (10) | −0.0051 (10) | −0.0212 (10) |
O10 | 0.0512 (10) | 0.0734 (14) | 0.0675 (14) | −0.0011 (10) | 0.0048 (10) | −0.0224 (11) |
C35 | 0.0390 (12) | 0.0360 (16) | 0.0491 (17) | −0.0022 (11) | −0.0097 (12) | −0.0078 (13) |
C36 | 0.0554 (15) | 0.0476 (18) | 0.0556 (19) | −0.0014 (13) | −0.0173 (14) | −0.0066 (15) |
C37 | 0.0607 (16) | 0.056 (2) | 0.0534 (18) | −0.0045 (14) | −0.0071 (14) | −0.0182 (16) |
C38 | 0.0513 (16) | 0.0441 (18) | 0.076 (2) | 0.0000 (13) | 0.0015 (15) | −0.0173 (17) |
C39 | 0.0391 (13) | 0.0434 (18) | 0.078 (2) | 0.0013 (12) | −0.0110 (14) | −0.0025 (16) |
C40 | 0.0349 (12) | 0.0421 (17) | 0.0497 (17) | −0.0046 (11) | −0.0065 (12) | −0.0061 (14) |
C41 | 0.0534 (16) | 0.0418 (17) | 0.0538 (19) | −0.0029 (13) | −0.0230 (15) | −0.0035 (15) |
C42 | 0.0463 (13) | 0.0345 (15) | 0.0429 (16) | −0.0040 (11) | −0.0125 (12) | −0.0085 (13) |
C43 | 0.0541 (15) | 0.0461 (18) | 0.0496 (17) | 0.0006 (13) | −0.0155 (13) | −0.0048 (14) |
C44 | 0.0695 (18) | 0.0395 (18) | 0.062 (2) | −0.0041 (14) | −0.0153 (15) | 0.0013 (15) |
C45 | 0.0615 (16) | 0.0373 (18) | 0.073 (2) | −0.0146 (13) | −0.0149 (15) | −0.0038 (15) |
C46 | 0.0473 (14) | 0.0411 (17) | 0.0625 (19) | −0.0057 (12) | −0.0148 (13) | −0.0107 (14) |
C47 | 0.0434 (13) | 0.0293 (14) | 0.0438 (15) | −0.0015 (11) | −0.0114 (11) | −0.0085 (12) |
C48 | 0.0449 (14) | 0.0388 (17) | 0.0537 (17) | −0.0023 (12) | −0.0152 (13) | −0.0092 (13) |
C49 | 0.0447 (13) | 0.0330 (15) | 0.0452 (16) | −0.0010 (11) | −0.0173 (12) | 0.0001 (12) |
C50 | 0.0447 (13) | 0.0365 (16) | 0.0402 (15) | 0.0008 (12) | −0.0126 (12) | −0.0047 (12) |
C51 | 0.0396 (13) | 0.0398 (16) | 0.0417 (15) | −0.0017 (12) | −0.0107 (11) | −0.0012 (13) |
C52 | 0.0446 (13) | 0.0345 (15) | 0.0378 (15) | −0.0021 (11) | −0.0132 (12) | −0.0017 (12) |
C53 | 0.0441 (13) | 0.0302 (15) | 0.0385 (15) | −0.0020 (11) | −0.0099 (11) | −0.0018 (12) |
C54 | 0.0410 (12) | 0.0326 (15) | 0.0391 (15) | −0.0015 (11) | −0.0110 (11) | 0.0005 (12) |
C55 | 0.0433 (13) | 0.0377 (16) | 0.0411 (15) | −0.0033 (12) | −0.0116 (11) | 0.0031 (13) |
C56 | 0.0494 (15) | 0.0491 (18) | 0.0607 (19) | −0.0084 (13) | −0.0141 (14) | −0.0049 (14) |
C57 | 0.0477 (16) | 0.069 (2) | 0.060 (2) | −0.0134 (14) | −0.0068 (14) | 0.0000 (17) |
C58 | 0.0437 (15) | 0.081 (2) | 0.0511 (19) | 0.0006 (15) | −0.0039 (13) | −0.0053 (17) |
C59 | 0.0556 (16) | 0.0553 (19) | 0.0451 (17) | 0.0032 (14) | −0.0065 (13) | −0.0103 (14) |
C60 | 0.0468 (14) | 0.0416 (17) | 0.0359 (15) | −0.0014 (12) | −0.0077 (12) | 0.0020 (13) |
C61 | 0.0544 (15) | 0.0363 (16) | 0.0381 (16) | 0.0004 (12) | −0.0098 (12) | −0.0035 (13) |
C62 | 0.0439 (14) | 0.0572 (19) | 0.0432 (17) | −0.0035 (13) | −0.0097 (13) | −0.0041 (14) |
C63 | 0.0490 (15) | 0.0465 (17) | 0.0412 (16) | −0.0106 (13) | −0.0118 (12) | −0.0005 (13) |
C64 | 0.0530 (15) | 0.067 (2) | 0.0444 (17) | −0.0185 (15) | −0.0061 (13) | 0.0002 (15) |
C65 | 0.0689 (19) | 0.063 (2) | 0.067 (2) | −0.0283 (16) | −0.0184 (17) | 0.0078 (17) |
C66 | 0.079 (2) | 0.0478 (19) | 0.072 (2) | −0.0239 (16) | −0.0221 (18) | −0.0035 (16) |
C67 | 0.0564 (15) | 0.0445 (18) | 0.0618 (19) | −0.0145 (13) | −0.0151 (14) | −0.0030 (15) |
C68 | 0.0473 (14) | 0.0402 (16) | 0.0406 (15) | −0.0107 (12) | −0.0151 (12) | −0.0003 (13) |
O1—C6 | 1.407 (3) | C24—H24 | 0.9300 |
O1—C7 | 1.372 (3) | C25—H25 | 0.9300 |
O2—C7 | 1.184 (4) | C30—H30 | 0.9300 |
O3—C14 | 1.223 (3) | C31—H31 | 0.9300 |
O4—C27 | 1.212 (3) | C32—H32 | 0.9300 |
O5—C28 | 1.217 (3) | C33—H33 | 0.9300 |
O6—C40 | 1.405 (3) | C35—C36 | 1.387 (4) |
O6—C41 | 1.364 (3) | C35—C40 | 1.382 (3) |
O7—C41 | 1.200 (3) | C35—C50 | 1.491 (3) |
O8—C48 | 1.214 (3) | C36—C37 | 1.382 (4) |
O9—C61 | 1.219 (3) | C37—C38 | 1.366 (4) |
O10—C62 | 1.213 (3) | C38—C39 | 1.384 (4) |
C1—C16 | 1.493 (3) | C39—C40 | 1.367 (4) |
C1—C6 | 1.381 (4) | C41—C42 | 1.502 (4) |
C1—C2 | 1.382 (4) | C42—C43 | 1.396 (3) |
C2—C3 | 1.401 (5) | C42—C47 | 1.400 (3) |
C3—C4 | 1.382 (5) | C43—C44 | 1.371 (4) |
C4—C5 | 1.356 (5) | C44—C45 | 1.374 (4) |
C5—C6 | 1.374 (4) | C45—C46 | 1.370 (4) |
C7—C8 | 1.495 (4) | C46—C47 | 1.393 (3) |
C8—C13 | 1.386 (4) | C47—C48 | 1.489 (3) |
C8—C9 | 1.386 (4) | C48—C49 | 1.507 (3) |
C9—C10 | 1.366 (5) | C49—C50 | 1.413 (3) |
C10—C11 | 1.363 (5) | C49—C54 | 1.396 (3) |
C11—C12 | 1.375 (4) | C50—C51 | 1.378 (3) |
C12—C13 | 1.396 (4) | C51—C52 | 1.411 (3) |
C13—C14 | 1.480 (4) | C51—C62 | 1.505 (4) |
C14—C15 | 1.509 (3) | C52—C53 | 1.385 (3) |
C15—C20 | 1.392 (3) | C52—C68 | 1.484 (3) |
C15—C16 | 1.415 (3) | C53—C54 | 1.414 (3) |
C16—C17 | 1.385 (3) | C53—C61 | 1.500 (3) |
C17—C28 | 1.496 (3) | C54—C55 | 1.485 (3) |
C17—C18 | 1.412 (3) | C55—C56 | 1.390 (3) |
C18—C19 | 1.384 (3) | C55—C60 | 1.391 (3) |
C18—C34 | 1.491 (3) | C56—C57 | 1.391 (4) |
C19—C27 | 1.499 (3) | C57—C58 | 1.364 (4) |
C19—C20 | 1.417 (3) | C58—C59 | 1.381 (4) |
C20—C21 | 1.493 (3) | C59—C60 | 1.381 (4) |
C21—C22 | 1.391 (4) | C60—C61 | 1.486 (4) |
C21—C26 | 1.387 (3) | C62—C63 | 1.486 (4) |
C22—C23 | 1.393 (4) | C63—C64 | 1.379 (4) |
C23—C24 | 1.365 (4) | C63—C68 | 1.391 (3) |
C24—C25 | 1.384 (4) | C64—C65 | 1.376 (4) |
C25—C26 | 1.379 (4) | C65—C66 | 1.381 (4) |
C26—C27 | 1.487 (4) | C66—C67 | 1.386 (4) |
C28—C29 | 1.481 (4) | C67—C68 | 1.376 (4) |
C29—C30 | 1.377 (4) | C36—H36 | 0.9300 |
C29—C34 | 1.397 (3) | C37—H37 | 0.9300 |
C30—C31 | 1.371 (4) | C38—H38 | 0.9300 |
C31—C32 | 1.380 (4) | C39—H39 | 0.9300 |
C32—C33 | 1.397 (4) | C43—H43 | 0.9300 |
C33—C34 | 1.384 (3) | C44—H44 | 0.9300 |
C2—H2 | 0.9300 | C45—H45 | 0.9300 |
C3—H3 | 0.9300 | C46—H46 | 0.9300 |
C4—H4 | 0.9300 | C56—H56 | 0.9300 |
C5—H5 | 0.9300 | C57—H57 | 0.9300 |
C9—H9 | 0.9300 | C58—H58 | 0.9300 |
C10—H10 | 0.9300 | C59—H59 | 0.9300 |
C11—H11 | 0.9300 | C64—H64 | 0.9300 |
C12—H12 | 0.9300 | C65—H65 | 0.9300 |
C22—H22 | 0.9300 | C66—H66 | 0.9300 |
C23—H23 | 0.9300 | C67—H67 | 0.9300 |
C6—O1—C7 | 119.8 (2) | C34—C33—H33 | 121.00 |
C40—O6—C41 | 118.32 (19) | C36—C35—C40 | 117.6 (2) |
C2—C1—C6 | 117.7 (3) | C36—C35—C50 | 124.1 (2) |
C6—C1—C16 | 118.7 (2) | C40—C35—C50 | 118.3 (2) |
C2—C1—C16 | 123.5 (3) | C35—C36—C37 | 120.4 (2) |
C1—C2—C3 | 119.9 (3) | C36—C37—C38 | 120.3 (3) |
C2—C3—C4 | 119.5 (3) | C37—C38—C39 | 120.5 (2) |
C3—C4—C5 | 121.5 (3) | C38—C39—C40 | 118.4 (2) |
C4—C5—C6 | 117.9 (3) | O6—C40—C35 | 117.1 (2) |
O1—C6—C1 | 116.9 (2) | O6—C40—C39 | 120.0 (2) |
C1—C6—C5 | 123.5 (3) | C35—C40—C39 | 122.8 (2) |
O1—C6—C5 | 119.4 (2) | O6—C41—O7 | 118.8 (2) |
O1—C7—C8 | 115.4 (2) | O6—C41—C42 | 117.4 (2) |
O2—C7—C8 | 126.7 (3) | O7—C41—C42 | 123.2 (2) |
O1—C7—O2 | 117.5 (2) | C41—C42—C43 | 113.4 (2) |
C7—C8—C9 | 114.1 (3) | C41—C42—C47 | 127.3 (2) |
C9—C8—C13 | 119.6 (3) | C43—C42—C47 | 119.3 (2) |
C7—C8—C13 | 126.2 (2) | C42—C43—C44 | 120.9 (2) |
C8—C9—C10 | 120.6 (3) | C43—C44—C45 | 120.1 (2) |
C9—C10—C11 | 120.3 (3) | C44—C45—C46 | 119.7 (2) |
C10—C11—C12 | 120.4 (3) | C45—C46—C47 | 121.8 (2) |
C11—C12—C13 | 120.3 (3) | C42—C47—C46 | 118.2 (2) |
C8—C13—C12 | 118.9 (2) | C42—C47—C48 | 125.6 (2) |
C12—C13—C14 | 115.6 (2) | C46—C47—C48 | 116.3 (2) |
C8—C13—C14 | 125.5 (2) | O8—C48—C47 | 120.1 (2) |
O3—C14—C13 | 119.3 (2) | O8—C48—C49 | 118.8 (2) |
C13—C14—C15 | 124.9 (2) | C47—C48—C49 | 121.1 (2) |
O3—C14—C15 | 115.8 (2) | C48—C49—C50 | 119.7 (2) |
C14—C15—C20 | 119.5 (2) | C48—C49—C54 | 121.1 (2) |
C16—C15—C20 | 119.0 (2) | C50—C49—C54 | 119.2 (2) |
C14—C15—C16 | 120.9 (2) | C35—C50—C49 | 118.5 (2) |
C1—C16—C17 | 120.0 (2) | C35—C50—C51 | 122.5 (2) |
C15—C16—C17 | 118.8 (2) | C49—C50—C51 | 118.9 (2) |
C1—C16—C15 | 121.1 (2) | C50—C51—C52 | 122.8 (2) |
C16—C17—C28 | 129.3 (2) | C50—C51—C62 | 129.1 (2) |
C18—C17—C28 | 108.1 (2) | C52—C51—C62 | 108.1 (2) |
C16—C17—C18 | 122.7 (2) | C51—C52—C53 | 118.1 (2) |
C17—C18—C19 | 118.3 (2) | C51—C52—C68 | 108.5 (2) |
C19—C18—C34 | 133.3 (2) | C53—C52—C68 | 133.4 (2) |
C17—C18—C34 | 108.4 (2) | C52—C53—C54 | 120.1 (2) |
C18—C19—C20 | 119.8 (2) | C52—C53—C61 | 132.1 (2) |
C20—C19—C27 | 108.3 (2) | C54—C53—C61 | 107.9 (2) |
C18—C19—C27 | 132.0 (2) | C49—C54—C53 | 120.8 (2) |
C15—C20—C21 | 130.3 (2) | C49—C54—C55 | 130.5 (2) |
C19—C20—C21 | 108.3 (2) | C53—C54—C55 | 108.6 (2) |
C15—C20—C19 | 121.4 (2) | C54—C55—C56 | 132.4 (2) |
C20—C21—C22 | 132.7 (2) | C54—C55—C60 | 108.3 (2) |
C20—C21—C26 | 108.1 (2) | C56—C55—C60 | 119.3 (2) |
C22—C21—C26 | 119.1 (2) | C55—C56—C57 | 118.1 (2) |
C21—C22—C23 | 117.9 (2) | C56—C57—C58 | 121.9 (2) |
C22—C23—C24 | 122.5 (3) | C57—C58—C59 | 120.8 (3) |
C23—C24—C25 | 120.0 (2) | C58—C59—C60 | 117.9 (2) |
C24—C25—C26 | 118.1 (2) | C55—C60—C59 | 122.1 (2) |
C21—C26—C25 | 122.5 (2) | C55—C60—C61 | 109.5 (2) |
C21—C26—C27 | 110.1 (2) | C59—C60—C61 | 128.4 (2) |
C25—C26—C27 | 127.4 (2) | O9—C61—C53 | 128.1 (2) |
O4—C27—C19 | 128.0 (2) | O9—C61—C60 | 126.4 (2) |
O4—C27—C26 | 126.9 (2) | C53—C61—C60 | 105.4 (2) |
C19—C27—C26 | 105.1 (2) | O10—C62—C51 | 127.0 (2) |
O5—C28—C29 | 126.9 (2) | O10—C62—C63 | 127.8 (2) |
C17—C28—C29 | 105.9 (2) | C51—C62—C63 | 105.2 (2) |
O5—C28—C17 | 127.2 (2) | C62—C63—C64 | 128.8 (2) |
C28—C29—C30 | 128.9 (2) | C62—C63—C68 | 109.6 (2) |
C30—C29—C34 | 121.8 (2) | C64—C63—C68 | 121.6 (2) |
C28—C29—C34 | 109.3 (2) | C63—C64—C65 | 118.5 (2) |
C29—C30—C31 | 118.2 (2) | C64—C65—C66 | 120.0 (3) |
C30—C31—C32 | 121.0 (2) | C65—C66—C67 | 121.7 (3) |
C31—C32—C33 | 121.3 (2) | C66—C67—C68 | 118.3 (2) |
C32—C33—C34 | 117.9 (2) | C52—C68—C63 | 108.6 (2) |
C18—C34—C29 | 108.3 (2) | C52—C68—C67 | 131.6 (2) |
C29—C34—C33 | 119.8 (2) | C63—C68—C67 | 119.8 (2) |
C18—C34—C33 | 131.8 (2) | C35—C36—H36 | 120.00 |
C1—C2—H2 | 120.00 | C37—C36—H36 | 120.00 |
C3—C2—H2 | 120.00 | C36—C37—H37 | 120.00 |
C4—C3—H3 | 120.00 | C38—C37—H37 | 120.00 |
C2—C3—H3 | 120.00 | C37—C38—H38 | 120.00 |
C5—C4—H4 | 119.00 | C39—C38—H38 | 120.00 |
C3—C4—H4 | 119.00 | C38—C39—H39 | 121.00 |
C4—C5—H5 | 121.00 | C40—C39—H39 | 121.00 |
C6—C5—H5 | 121.00 | C42—C43—H43 | 120.00 |
C8—C9—H9 | 120.00 | C44—C43—H43 | 120.00 |
C10—C9—H9 | 120.00 | C43—C44—H44 | 120.00 |
C11—C10—H10 | 120.00 | C45—C44—H44 | 120.00 |
C9—C10—H10 | 120.00 | C44—C45—H45 | 120.00 |
C10—C11—H11 | 120.00 | C46—C45—H45 | 120.00 |
C12—C11—H11 | 120.00 | C45—C46—H46 | 119.00 |
C13—C12—H12 | 120.00 | C47—C46—H46 | 119.00 |
C11—C12—H12 | 120.00 | C55—C56—H56 | 121.00 |
C21—C22—H22 | 121.00 | C57—C56—H56 | 121.00 |
C23—C22—H22 | 121.00 | C56—C57—H57 | 119.00 |
C24—C23—H23 | 119.00 | C58—C57—H57 | 119.00 |
C22—C23—H23 | 119.00 | C57—C58—H58 | 120.00 |
C23—C24—H24 | 120.00 | C59—C58—H58 | 120.00 |
C25—C24—H24 | 120.00 | C58—C59—H59 | 121.00 |
C26—C25—H25 | 121.00 | C60—C59—H59 | 121.00 |
C24—C25—H25 | 121.00 | C63—C64—H64 | 121.00 |
C29—C30—H30 | 121.00 | C65—C64—H64 | 121.00 |
C31—C30—H30 | 121.00 | C64—C65—H65 | 120.00 |
C32—C31—H31 | 119.00 | C66—C65—H65 | 120.00 |
C30—C31—H31 | 119.00 | C65—C66—H66 | 119.00 |
C31—C32—H32 | 119.00 | C67—C66—H66 | 119.00 |
C33—C32—H32 | 119.00 | C66—C67—H67 | 121.00 |
C32—C33—H33 | 121.00 | C68—C67—H67 | 121.00 |
C7—O1—C6—C1 | −76.7 (3) | C30—C31—C32—C33 | 0.2 (4) |
C7—O1—C6—C5 | 107.8 (3) | C31—C32—C33—C34 | 0.2 (4) |
C6—O1—C7—O2 | 166.9 (2) | C32—C33—C34—C18 | −179.5 (2) |
C6—O1—C7—C8 | −20.1 (3) | C32—C33—C34—C29 | −0.5 (4) |
C40—O6—C41—C42 | 32.3 (3) | C50—C35—C40—O6 | −5.5 (3) |
C41—O6—C40—C35 | 69.9 (3) | C50—C35—C40—C39 | 178.5 (2) |
C41—O6—C40—C39 | −114.0 (3) | C36—C35—C50—C49 | 90.7 (3) |
C40—O6—C41—O7 | −156.0 (2) | C36—C35—C50—C51 | −93.5 (3) |
C16—C1—C6—C5 | 175.9 (2) | C40—C35—C50—C49 | −87.4 (3) |
C2—C1—C16—C15 | −102.7 (3) | C40—C35—C50—C51 | 88.4 (3) |
C2—C1—C16—C17 | 79.1 (3) | C36—C35—C40—O6 | 176.3 (2) |
C16—C1—C6—O1 | 0.5 (3) | C36—C35—C40—C39 | 0.3 (4) |
C16—C1—C2—C3 | −175.6 (2) | C40—C35—C36—C37 | −0.8 (4) |
C2—C1—C6—O1 | −175.7 (2) | C50—C35—C36—C37 | −178.9 (2) |
C2—C1—C6—C5 | −0.3 (4) | C35—C36—C37—C38 | 0.9 (4) |
C6—C1—C16—C15 | 81.4 (3) | C36—C37—C38—C39 | −0.4 (4) |
C6—C1—C16—C17 | −96.8 (3) | C37—C38—C39—C40 | −0.1 (4) |
C6—C1—C2—C3 | 0.3 (4) | C38—C39—C40—O6 | −175.8 (2) |
C1—C2—C3—C4 | −0.4 (4) | C38—C39—C40—C35 | 0.1 (4) |
C2—C3—C4—C5 | 0.4 (5) | O6—C41—C42—C43 | 93.9 (3) |
C3—C4—C5—C6 | −0.4 (5) | O6—C41—C42—C47 | −88.4 (3) |
C4—C5—C6—C1 | 0.3 (4) | O7—C41—C42—C43 | −77.4 (3) |
C4—C5—C6—O1 | 175.6 (3) | O7—C41—C42—C47 | 100.3 (3) |
O2—C7—C8—C13 | −98.7 (4) | C41—C42—C43—C44 | 176.9 (2) |
O1—C7—C8—C9 | −92.2 (3) | C47—C42—C43—C44 | −1.0 (4) |
O1—C7—C8—C13 | 89.0 (3) | C41—C42—C47—C46 | −177.4 (2) |
O2—C7—C8—C9 | 80.1 (3) | C41—C42—C47—C48 | 1.4 (4) |
C13—C8—C9—C10 | −0.4 (4) | C43—C42—C47—C46 | 0.2 (3) |
C7—C8—C13—C12 | 177.7 (2) | C43—C42—C47—C48 | 179.0 (2) |
C7—C8—C9—C10 | −179.3 (3) | C42—C43—C44—C45 | 0.9 (4) |
C7—C8—C13—C14 | −1.3 (4) | C43—C44—C45—C46 | 0.0 (4) |
C9—C8—C13—C12 | −1.1 (4) | C44—C45—C46—C47 | −0.9 (4) |
C9—C8—C13—C14 | 179.9 (2) | C45—C46—C47—C42 | 0.7 (4) |
C8—C9—C10—C11 | 1.5 (5) | C45—C46—C47—C48 | −178.2 (2) |
C9—C10—C11—C12 | −1.3 (5) | C42—C47—C48—O8 | 172.3 (2) |
C10—C11—C12—C13 | −0.2 (5) | C42—C47—C48—C49 | −9.8 (4) |
C11—C12—C13—C8 | 1.4 (4) | C46—C47—C48—O8 | −8.8 (4) |
C11—C12—C13—C14 | −179.5 (3) | C46—C47—C48—C49 | 169.1 (2) |
C12—C13—C14—C15 | 173.4 (2) | O8—C48—C49—C50 | −104.7 (3) |
C12—C13—C14—O3 | −7.1 (4) | O8—C48—C49—C54 | 74.2 (3) |
C8—C13—C14—O3 | 172.0 (2) | C47—C48—C49—C50 | 77.4 (3) |
C8—C13—C14—C15 | −7.5 (4) | C47—C48—C49—C54 | −103.8 (3) |
O3—C14—C15—C20 | −57.0 (3) | C48—C49—C50—C35 | −4.8 (3) |
C13—C14—C15—C16 | −66.4 (3) | C48—C49—C50—C51 | 179.3 (2) |
C13—C14—C15—C20 | 122.5 (3) | C54—C49—C50—C35 | 176.3 (2) |
O3—C14—C15—C16 | 114.1 (3) | C54—C49—C50—C51 | 0.4 (3) |
C14—C15—C20—C19 | 169.2 (2) | C48—C49—C54—C53 | 177.8 (2) |
C14—C15—C20—C21 | −12.7 (4) | C48—C49—C54—C55 | −0.7 (4) |
C16—C15—C20—C19 | −2.1 (3) | C50—C49—C54—C53 | −3.3 (3) |
C14—C15—C16—C1 | 12.4 (3) | C50—C49—C54—C55 | 178.1 (2) |
C14—C15—C16—C17 | −169.4 (2) | C35—C50—C51—C52 | −174.9 (2) |
C20—C15—C16—C1 | −176.5 (2) | C35—C50—C51—C62 | 3.5 (4) |
C20—C15—C16—C17 | 1.8 (3) | C49—C50—C51—C52 | 0.9 (4) |
C16—C15—C20—C21 | 176.0 (2) | C49—C50—C51—C62 | 179.3 (2) |
C15—C16—C17—C28 | −177.8 (2) | C50—C51—C52—C53 | 0.7 (3) |
C1—C16—C17—C18 | 178.6 (2) | C50—C51—C52—C68 | −178.8 (2) |
C1—C16—C17—C28 | 0.4 (4) | C62—C51—C52—C53 | −177.9 (2) |
C15—C16—C17—C18 | 0.4 (4) | C62—C51—C52—C68 | 2.5 (3) |
C16—C17—C18—C34 | 178.5 (2) | C50—C51—C62—O10 | 0.0 (4) |
C28—C17—C18—C19 | 176.3 (2) | C50—C51—C62—C63 | 179.6 (2) |
C16—C17—C18—C19 | −2.3 (4) | C52—C51—C62—O10 | 178.5 (3) |
C18—C17—C28—C29 | 3.2 (3) | C52—C51—C62—C63 | −1.8 (3) |
C16—C17—C28—O5 | 3.2 (4) | C51—C52—C53—C54 | −3.6 (3) |
C16—C17—C28—C29 | −178.4 (2) | C51—C52—C53—C61 | 176.0 (2) |
C28—C17—C18—C34 | −3.0 (3) | C68—C52—C53—C54 | 175.8 (2) |
C18—C17—C28—O5 | −175.2 (3) | C68—C52—C53—C61 | −4.6 (5) |
C17—C18—C19—C20 | 1.9 (3) | C51—C52—C68—C63 | −2.3 (3) |
C17—C18—C19—C27 | −177.0 (2) | C51—C52—C68—C67 | 176.5 (3) |
C19—C18—C34—C29 | −177.5 (3) | C53—C52—C68—C63 | 178.3 (3) |
C19—C18—C34—C33 | 1.7 (5) | C53—C52—C68—C67 | −3.0 (5) |
C17—C18—C34—C33 | −179.3 (3) | C52—C53—C54—C49 | 5.0 (3) |
C34—C18—C19—C20 | −179.1 (2) | C52—C53—C54—C55 | −176.2 (2) |
C34—C18—C19—C27 | 2.1 (5) | C61—C53—C54—C49 | −174.7 (2) |
C17—C18—C34—C29 | 1.6 (3) | C61—C53—C54—C55 | 4.2 (3) |
C18—C19—C20—C21 | −178.3 (2) | C52—C53—C61—O9 | −8.4 (4) |
C27—C19—C20—C15 | 179.3 (2) | C52—C53—C61—C60 | 175.4 (2) |
C27—C19—C20—C21 | 0.9 (3) | C54—C53—C61—O9 | 171.2 (2) |
C18—C19—C20—C15 | 0.2 (4) | C54—C53—C61—C60 | −5.1 (3) |
C18—C19—C27—O4 | −3.8 (5) | C49—C54—C55—C56 | −3.9 (4) |
C18—C19—C27—C26 | 176.9 (2) | C49—C54—C55—C60 | 177.1 (2) |
C20—C19—C27—O4 | 177.3 (3) | C53—C54—C55—C56 | 177.5 (3) |
C20—C19—C27—C26 | −2.1 (3) | C53—C54—C55—C60 | −1.6 (3) |
C15—C20—C21—C26 | −177.5 (2) | C54—C55—C56—C57 | −178.9 (2) |
C19—C20—C21—C22 | 178.0 (3) | C60—C55—C56—C57 | 0.1 (4) |
C15—C20—C21—C22 | −0.3 (5) | C54—C55—C60—C59 | 179.4 (2) |
C19—C20—C21—C26 | 0.8 (3) | C54—C55—C60—C61 | −1.7 (3) |
C20—C21—C26—C27 | −2.2 (3) | C56—C55—C60—C59 | 0.2 (4) |
C22—C21—C26—C27 | −179.8 (2) | C56—C55—C60—C61 | 179.1 (2) |
C26—C21—C22—C23 | 0.8 (4) | C55—C56—C57—C58 | 0.6 (4) |
C22—C21—C26—C25 | −0.4 (4) | C56—C57—C58—C59 | −1.6 (4) |
C20—C21—C22—C23 | −176.2 (3) | C57—C58—C59—C60 | 1.8 (4) |
C20—C21—C26—C25 | 177.3 (2) | C58—C59—C60—C55 | −1.1 (4) |
C21—C22—C23—C24 | −0.4 (4) | C58—C59—C60—C61 | −179.8 (2) |
C22—C23—C24—C25 | −0.4 (4) | C55—C60—C61—O9 | −172.2 (2) |
C23—C24—C25—C26 | 0.8 (4) | C55—C60—C61—C53 | 4.1 (3) |
C24—C25—C26—C21 | −0.4 (4) | C59—C60—C61—O9 | 6.7 (4) |
C24—C25—C26—C27 | 179.0 (2) | C59—C60—C61—C53 | −177.0 (2) |
C21—C26—C27—C19 | 2.6 (3) | O10—C62—C63—C64 | 2.3 (5) |
C25—C26—C27—O4 | 3.9 (4) | O10—C62—C63—C68 | −179.9 (3) |
C21—C26—C27—O4 | −176.7 (3) | C51—C62—C63—C64 | −177.4 (2) |
C25—C26—C27—C19 | −176.8 (2) | C51—C62—C63—C68 | 0.4 (3) |
C17—C28—C29—C34 | −2.2 (3) | C62—C63—C64—C65 | 177.1 (3) |
C17—C28—C29—C30 | 178.5 (2) | C68—C63—C64—C65 | −0.5 (4) |
O5—C28—C29—C30 | −3.1 (4) | C62—C63—C68—C52 | 1.1 (3) |
O5—C28—C29—C34 | 176.2 (3) | C62—C63—C68—C67 | −177.9 (2) |
C34—C29—C30—C31 | −0.3 (4) | C64—C63—C68—C52 | 179.1 (2) |
C28—C29—C34—C18 | 0.4 (3) | C64—C63—C68—C67 | 0.2 (4) |
C28—C29—C34—C33 | −178.8 (2) | C63—C64—C65—C66 | 0.4 (4) |
C28—C29—C30—C31 | 179.0 (3) | C64—C65—C66—C67 | 0.1 (4) |
C30—C29—C34—C18 | 179.8 (2) | C65—C66—C67—C68 | −0.5 (4) |
C30—C29—C34—C33 | 0.6 (4) | C66—C67—C68—C52 | −178.3 (3) |
C29—C30—C31—C32 | −0.1 (4) | C66—C67—C68—C63 | 0.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O3 | 0.93 | 2.37 | 2.693 (3) | 100 |
C22—H22···O3 | 0.93 | 2.50 | 3.081 (3) | 121 |
C24—H24···O10i | 0.93 | 2.56 | 3.302 (3) | 137 |
C30—H30···O5ii | 0.93 | 2.60 | 3.507 (3) | 166 |
C32—H32···O7iii | 0.93 | 2.49 | 3.398 (3) | 166 |
C33—H33···O4 | 0.93 | 2.32 | 3.087 (3) | 139 |
C39—H39···O1iv | 0.93 | 2.36 | 3.115 (3) | 139 |
C46—H46···O8 | 0.93 | 2.40 | 2.728 (3) | 101 |
C56—H56···O8 | 0.93 | 2.52 | 3.210 (3) | 131 |
C58—H58···O7v | 0.93 | 2.52 | 3.377 (3) | 154 |
C67—H67···O9 | 0.93 | 2.36 | 3.117 (3) | 139 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x, −y+1, −z+2; (iii) x−1, y, z; (iv) x+1, y−1, z; (v) −x+1, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C34H16O5 |
Mr | 504.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 12.230 (4), 12.346 (3), 16.794 (5) |
α, β, γ (°) | 82.229 (7), 72.773 (6), 81.181 (10) |
V (Å3) | 2382.5 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.28 × 0.18 × 0.14 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.980, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38137, 10895, 4858 |
Rint | 0.061 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.135, 0.94 |
No. of reflections | 10895 |
No. of parameters | 704 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.21 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24···O10i | 0.93 | 2.56 | 3.302 (3) | 137. |
C30—H30···O5ii | 0.93 | 2.60 | 3.507 (3) | 166. |
C32—H32···O7iii | 0.93 | 2.49 | 3.398 (3) | 166. |
C33—H33···O4 | 0.93 | 2.32 | 3.087 (3) | 139. |
C39—H39···O1iv | 0.93 | 2.36 | 3.115 (3) | 139. |
C56—H56···O8 | 0.93 | 2.52 | 3.210 (3) | 131. |
C58—H58···O7v | 0.93 | 2.52 | 3.377 (3) | 154. |
C67—H67···O9 | 0.93 | 2.36 | 3.117 (3) | 139. |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x, −y+1, −z+2; (iii) x−1, y, z; (iv) x+1, y−1, z; (v) −x+1, −y, −z+2. |
Acknowledgements
The authors are grateful to the Higher Education Ministry of Egypt, Manchester Metropolitan University, Erciyes University and the University of Sargodha for supporting this study.
References
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1,3-indandione is an important member of class of 1,3-diketo compounds. It is a very strong C-nucleophile. It undergoes self-condensation quite easily, resulting in a dimer e.g. bindone and trimer (Zargar & Khan, 2012). Due to such unusual chemical reactivity, 1,3-indandione showed a wide range of industrial and pharmaceutical applications. It is a founder structure in most of non linear optical (NLO) compounds, chromophores (Seniutinas et al., 2012) and pesticide molecules such as diphacinone, chlorophacinone, valone, and Pindone (Jin et al., 2009). Such facts prompted us to synthesize and study the crystal determination of the title compound (I).
Figures 1 and 2 show two enantiomeric molecules (A with O1 and B with O6) of the title compound in the asymmetric unit. The values of the geometric parameters of both molecules A and B are similar with each other. In molecule A, the two benzene rings (C1–C6 and C8–C13) which are attached to the nine-membered ring are inclined to one another by 63.62 (14)°, and in molecule B, the two benzene rings (C35–C40 and C42–C47) by 68.23 (12)°.
In molecule A, the puckering parameters for the nine-membered ring (O1/C1/C6—C8/C13—C16) are Q(2) = 1.880 (3) Å, ϕ (2) = 58.83 (8)°; Q(3) = 0.189 (2) Å, ϕ (3) = 10.2 (8)°; Q(4) = 0.118 (3) Å, ϕ (4) = 136.5 (12) ° and QT (total puckering amplitude) = 1.893 (3) Å (Cremer & Pople, 1975). In molecule B, the puckering parameters for the nine-membered ring (O6/C35/C40—C42/C47—C50) are Q(2) = 1.864 (3) Å, ϕ (2) = 246.61 (7) °; Q(3) = 0.223 (2) Å, ϕ (3) = 177.7 (7) °; Q(4) = 0.143 (2) Å, ϕ (4) = 313.4 (10) ° and QT (total puckering amplitude) = 1.882 (3) Å.
In the crystal, C—H···O hydrogen bonds link the A and B molecules (Fig. 3, Table 1). The crystal packing is stabilized by additional three π–π stacking interactions [Cg5···Cg31 (x, y, z) = 3.7572 (19) Å, Cg7···Cg32(-1 + x, y, z) = 3.6996 (19) Å and Cg31···Cg31(1 - x, -y, 2 - z) = 3.7043 (19) Å; where Cg5, Cg7, Cg31 and Cg32 are the centroids of the C15–C20, C29–C34, C55–C60 and C63–C68 rings, respectively].