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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 12| December 2012| Pages o3363-o3364

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

(Received 30 October 2012; accepted 9 November 2012; online 17 November 2012)

The asymmetric unit of the title compound, C34H16O5, 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 ππ stacking interactions [centroid–centroid distances = 3.7572 (19), 3.6996 (19) and 3.7043 (19) Å] are also observed. The unit cell 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.

Related literature

1,3-Indandione undergoes self-condensation quite easily, see: Zargar & Khan (2012[Zargar, N. D. & Khan, K. Z. (2012). Global J. Sci. Frontier Res. B, XII, 45-48.]). For industrial and biological applications of indandion containing compounds see: Seniutinas et al. (2012[Seniutinas, G., Tomasiunas, R., Czapilicki, R., Sahraoui, B., Daskeviciene, M., Getaut, V. & Balveicius, Z. (2012). Dyes Pigm. 95, 33-40.]); Jin et al. (2009[Jin, M.-C., Cai, M.-Q. & Chen, X.-H. (2009). J. Anal. Toxicol. 33, 294-300.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C34H16O5

  • Mr = 504.47

  • Triclinic, [P \overline 1]

  • a = 12.230 (4) Å

  • b = 12.346 (3) Å

  • c = 16.794 (5) Å

  • α = 82.229 (7)°

  • β = 72.773 (6)°

  • γ = 81.181 (10)°

  • V = 2382.5 (12) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.28 × 0.18 × 0.14 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.987

  • 38137 measured reflections

  • 10895 independent reflections

  • 4858 reflections with I > 2σ(I)

  • Rint = 0.061

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.135

  • S = 0.94

  • 10895 reflections

  • 704 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339-340.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

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 ππ 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].

Related literature top

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 top

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.

Refinement top

All H atoms were located geometrically and treated as riding atoms with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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).

Figures top
[Figure 1] 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.
[Figure 2] 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.
[Figure 3] 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.
(I) top
Crystal data top
C34H16O5Z = 4
Mr = 504.47F(000) = 1040
Triclinic, P1Dx = 1.406 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.230 (4) ÅCell parameters from 182 reflections
b = 12.346 (3) Åθ = 3.3–21.5°
c = 16.794 (5) ŵ = 0.10 mm1
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
Data collection top
Bruker Kappa APEXII CCD
diffractometer
10895 independent reflections
Radiation source: fine-focus sealed tube4858 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 0.81 pixels mm-1θmax = 27.6°, θmin = 2.3°
ω scansh = 1515
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1616
Tmin = 0.980, Tmax = 0.987l = 2121
38137 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-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 reflectionsΔρmax = 0.19 e Å3
704 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0020 (4)
Crystal data top
C34H16O5γ = 81.181 (10)°
Mr = 504.47V = 2382.5 (12) Å3
Triclinic, P1Z = 4
a = 12.230 (4) ÅMo Kα radiation
b = 12.346 (3) ŵ = 0.10 mm1
c = 16.794 (5) ÅT = 296 K
α = 82.229 (7)°0.28 × 0.18 × 0.14 mm
β = 72.773 (6)°
Data collection top
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 = 0.987Rint = 0.061
38137 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 0.94Δρmax = 0.19 e Å3
10895 reflectionsΔρmin = 0.21 e Å3
704 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.30343 (13)0.59668 (14)0.68545 (12)0.0606 (7)
O20.36189 (17)0.52360 (19)0.56612 (14)0.0919 (10)
O30.65201 (14)0.36139 (15)0.71664 (13)0.0755 (8)
O40.31239 (15)0.02705 (15)0.72691 (12)0.0721 (8)
O50.12537 (14)0.48837 (16)0.91275 (12)0.0710 (8)
C10.36124 (18)0.5327 (2)0.80850 (17)0.0457 (9)
C20.3815 (2)0.5551 (3)0.88099 (18)0.0660 (11)
C30.3712 (2)0.6644 (3)0.8990 (2)0.0826 (16)
C40.3414 (2)0.7490 (3)0.8436 (3)0.0847 (16)
C50.3211 (2)0.7288 (2)0.7722 (2)0.0709 (13)
C60.33166 (19)0.6210 (2)0.75593 (17)0.0495 (10)
C70.3894 (2)0.5616 (2)0.61735 (19)0.0570 (11)
C80.5070 (2)0.5881 (2)0.61130 (15)0.0474 (9)
C90.5342 (3)0.6868 (2)0.56465 (18)0.0692 (12)
C100.6393 (3)0.7211 (3)0.5530 (2)0.0821 (14)
C110.7199 (3)0.6572 (3)0.5856 (2)0.0797 (15)
C120.6954 (2)0.5587 (2)0.63184 (18)0.0616 (11)
C130.58751 (19)0.5234 (2)0.64604 (15)0.0431 (9)
C140.57028 (19)0.4167 (2)0.69716 (16)0.0462 (9)
C150.45753 (17)0.36805 (19)0.72787 (14)0.0400 (9)
C160.36222 (19)0.41890 (19)0.78720 (15)0.0422 (9)
C170.26743 (18)0.3624 (2)0.82399 (14)0.0415 (9)
C180.26223 (18)0.2556 (2)0.80507 (14)0.0407 (8)
C190.35423 (18)0.20753 (19)0.74519 (14)0.0403 (8)
C200.45172 (18)0.2643 (2)0.70666 (15)0.0416 (9)
C210.53516 (18)0.1954 (2)0.64342 (15)0.0445 (9)
C220.6417 (2)0.2118 (2)0.58698 (17)0.0609 (10)
C230.6949 (2)0.1317 (2)0.53227 (18)0.0672 (11)
C240.6467 (2)0.0389 (2)0.53273 (18)0.0659 (11)
C250.5414 (2)0.0214 (2)0.58938 (17)0.0585 (10)
C260.48748 (19)0.1004 (2)0.64358 (15)0.0449 (9)
C270.3741 (2)0.0999 (2)0.70820 (16)0.0482 (10)
C280.1557 (2)0.3987 (2)0.88562 (16)0.0477 (9)
C290.08788 (19)0.3041 (2)0.90507 (15)0.0456 (9)
C300.02000 (19)0.2945 (2)0.95961 (16)0.0532 (10)
C310.0662 (2)0.1982 (2)0.96602 (17)0.0588 (10)
C320.0065 (2)0.1132 (2)0.91909 (16)0.0556 (10)
C330.10298 (19)0.1220 (2)0.86364 (15)0.0503 (9)
C340.15016 (18)0.2189 (2)0.85727 (15)0.0417 (9)
O61.00908 (13)0.17362 (14)0.77863 (11)0.0535 (7)
O70.90062 (15)0.12612 (16)0.90231 (12)0.0674 (8)
O80.63534 (16)0.13362 (14)0.72125 (13)0.0714 (8)
O90.68213 (15)0.30354 (15)0.88768 (11)0.0639 (7)
O101.11392 (14)0.04935 (15)0.60688 (12)0.0679 (7)
C350.94112 (18)0.11759 (19)0.65889 (16)0.0419 (9)
C360.9417 (2)0.1352 (2)0.57890 (17)0.0529 (10)
C371.0053 (2)0.2271 (2)0.54203 (17)0.0577 (10)
C381.0671 (2)0.3024 (2)0.5844 (2)0.0609 (10)
C391.06743 (19)0.2873 (2)0.66449 (19)0.0557 (10)
C401.00473 (18)0.1955 (2)0.69976 (16)0.0433 (9)
C410.9114 (2)0.1772 (2)0.84396 (18)0.0483 (10)
C420.83080 (18)0.25756 (19)0.84404 (15)0.0409 (8)
C430.8502 (2)0.3585 (2)0.88940 (15)0.0504 (10)
C440.7807 (2)0.4394 (2)0.89913 (17)0.0586 (11)
C450.6915 (2)0.4225 (2)0.86307 (17)0.0573 (10)
C460.67236 (19)0.3245 (2)0.81736 (16)0.0498 (10)
C470.74017 (18)0.23984 (19)0.80699 (14)0.0389 (8)
C480.70772 (19)0.1365 (2)0.75803 (16)0.0453 (9)
C490.76039 (18)0.03298 (19)0.75539 (15)0.0407 (8)
C500.87355 (18)0.02196 (19)0.70404 (14)0.0408 (8)
C510.91980 (18)0.0738 (2)0.70171 (14)0.0411 (8)
C520.85951 (18)0.16119 (19)0.74945 (14)0.0391 (8)
C530.74977 (18)0.14884 (18)0.80130 (14)0.0384 (8)
C540.69851 (18)0.05350 (19)0.80181 (14)0.0383 (8)
C550.57903 (18)0.0654 (2)0.85817 (15)0.0416 (8)
C560.49093 (19)0.0013 (2)0.87878 (16)0.0531 (10)
C570.3861 (2)0.0352 (2)0.93379 (17)0.0606 (11)
C580.3681 (2)0.1337 (3)0.96666 (17)0.0616 (10)
C590.4552 (2)0.2002 (2)0.94781 (15)0.0542 (10)
C600.55958 (19)0.1651 (2)0.89297 (15)0.0433 (9)
C610.66597 (19)0.2206 (2)0.86300 (15)0.0443 (9)
C621.0373 (2)0.1048 (2)0.65342 (16)0.0490 (10)
C631.03846 (19)0.2175 (2)0.67471 (15)0.0456 (9)
C641.1243 (2)0.2854 (2)0.64486 (16)0.0558 (10)
C651.1039 (2)0.3894 (3)0.67096 (18)0.0656 (11)
C660.9996 (2)0.4235 (2)0.72629 (18)0.0645 (11)
C670.9133 (2)0.3553 (2)0.75702 (16)0.0538 (10)
C680.93334 (19)0.2515 (2)0.73056 (15)0.0418 (9)
H20.401900.497700.917800.0790*
H30.384400.680000.947800.0990*
H40.335200.821400.855500.1020*
H50.300600.786100.735400.0850*
H90.480300.730100.541100.0830*
H100.656000.788200.522600.0980*
H110.791800.680400.576600.0960*
H120.750900.515400.653700.0740*
H220.676200.274300.585800.0730*
H230.766000.141800.494000.0810*
H240.684600.012500.495000.0790*
H250.508000.041800.590900.0700*
H300.060400.351700.991200.0640*
H310.139000.190101.002500.0710*
H320.039700.048700.924500.0670*
H330.142900.064600.832000.0600*
H360.899000.084800.549900.0630*
H371.005900.237800.488100.0690*
H381.109200.364300.559200.0730*
H391.109300.338400.693600.0670*
H430.911100.371000.913300.0610*
H440.793900.505800.930200.0700*
H450.644300.477300.869700.0690*
H460.612400.314200.792500.0600*
H560.501800.068400.856400.0640*
H570.326500.008800.948600.0730*
H580.296300.156301.002200.0740*
H590.444000.266500.971300.0650*
H641.194500.261400.607900.0670*
H651.160400.436700.651300.0790*
H660.986900.494000.743400.0770*
H670.843700.379100.794600.0650*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0502 (10)0.0595 (13)0.0732 (14)0.0036 (9)0.0241 (10)0.0066 (11)
O20.0874 (15)0.120 (2)0.0876 (17)0.0121 (13)0.0433 (13)0.0343 (15)
O30.0540 (11)0.0714 (14)0.1047 (17)0.0081 (10)0.0386 (11)0.0168 (12)
O40.0663 (12)0.0524 (13)0.0930 (16)0.0217 (10)0.0010 (11)0.0229 (11)
O50.0637 (11)0.0605 (14)0.0801 (15)0.0056 (10)0.0023 (10)0.0303 (12)
C10.0398 (13)0.0489 (18)0.0484 (17)0.0110 (12)0.0061 (12)0.0121 (15)
C20.0640 (17)0.079 (2)0.058 (2)0.0239 (16)0.0094 (15)0.0167 (18)
C30.074 (2)0.108 (3)0.071 (3)0.039 (2)0.0024 (18)0.046 (2)
C40.066 (2)0.070 (3)0.113 (3)0.0272 (18)0.009 (2)0.047 (3)
C50.0593 (18)0.045 (2)0.103 (3)0.0059 (14)0.0089 (18)0.0208 (19)
C60.0387 (13)0.0469 (19)0.060 (2)0.0056 (12)0.0047 (13)0.0153 (16)
C70.0576 (17)0.0535 (19)0.060 (2)0.0011 (14)0.0209 (16)0.0051 (16)
C80.0522 (15)0.0397 (17)0.0469 (17)0.0037 (13)0.0083 (13)0.0073 (14)
C90.078 (2)0.052 (2)0.065 (2)0.0009 (16)0.0078 (17)0.0024 (17)
C100.092 (2)0.048 (2)0.083 (3)0.0186 (19)0.014 (2)0.0023 (18)
C110.0650 (19)0.076 (3)0.090 (3)0.0323 (18)0.0043 (18)0.012 (2)
C120.0518 (16)0.063 (2)0.069 (2)0.0189 (14)0.0096 (14)0.0059 (17)
C130.0436 (13)0.0426 (16)0.0430 (16)0.0102 (12)0.0084 (12)0.0071 (13)
C140.0397 (13)0.0490 (17)0.0516 (17)0.0043 (12)0.0153 (12)0.0067 (14)
C150.0401 (13)0.0363 (16)0.0442 (16)0.0060 (11)0.0122 (12)0.0037 (13)
C160.0449 (13)0.0376 (16)0.0455 (16)0.0076 (11)0.0138 (12)0.0031 (13)
C170.0419 (13)0.0399 (16)0.0440 (16)0.0050 (11)0.0125 (12)0.0079 (13)
C180.0410 (13)0.0414 (16)0.0409 (15)0.0057 (11)0.0132 (12)0.0031 (13)
C190.0428 (13)0.0373 (16)0.0404 (15)0.0049 (11)0.0105 (12)0.0054 (12)
C200.0425 (13)0.0378 (16)0.0435 (16)0.0050 (11)0.0124 (12)0.0006 (13)
C210.0409 (13)0.0420 (17)0.0479 (17)0.0008 (12)0.0112 (12)0.0022 (13)
C220.0512 (15)0.0572 (19)0.066 (2)0.0088 (14)0.0021 (15)0.0073 (16)
C230.0484 (15)0.066 (2)0.071 (2)0.0019 (15)0.0081 (15)0.0130 (18)
C240.0563 (17)0.062 (2)0.065 (2)0.0077 (15)0.0011 (15)0.0147 (17)
C250.0583 (16)0.0475 (18)0.067 (2)0.0006 (13)0.0134 (15)0.0134 (16)
C260.0454 (13)0.0424 (17)0.0434 (16)0.0007 (12)0.0094 (12)0.0061 (13)
C270.0484 (14)0.0433 (18)0.0525 (18)0.0041 (13)0.0125 (13)0.0087 (14)
C280.0477 (14)0.0460 (18)0.0477 (17)0.0008 (13)0.0096 (12)0.0126 (14)
C290.0430 (13)0.0502 (18)0.0448 (16)0.0072 (12)0.0126 (12)0.0059 (14)
C300.0469 (15)0.062 (2)0.0496 (18)0.0067 (13)0.0094 (13)0.0110 (15)
C310.0500 (15)0.071 (2)0.0520 (19)0.0132 (15)0.0069 (13)0.0040 (16)
C320.0579 (16)0.059 (2)0.0522 (18)0.0233 (14)0.0149 (14)0.0039 (15)
C330.0492 (14)0.0487 (18)0.0512 (17)0.0084 (13)0.0101 (13)0.0046 (14)
C340.0432 (13)0.0412 (16)0.0413 (16)0.0084 (12)0.0123 (12)0.0014 (13)
O60.0445 (10)0.0616 (13)0.0568 (12)0.0101 (8)0.0177 (9)0.0017 (10)
O70.0801 (13)0.0696 (14)0.0628 (14)0.0236 (10)0.0230 (11)0.0188 (11)
O80.0838 (13)0.0526 (13)0.0974 (16)0.0077 (10)0.0588 (12)0.0003 (11)
O90.0766 (12)0.0522 (13)0.0598 (13)0.0122 (10)0.0051 (10)0.0212 (10)
O100.0512 (10)0.0734 (14)0.0675 (14)0.0011 (10)0.0048 (10)0.0224 (11)
C350.0390 (12)0.0360 (16)0.0491 (17)0.0022 (11)0.0097 (12)0.0078 (13)
C360.0554 (15)0.0476 (18)0.0556 (19)0.0014 (13)0.0173 (14)0.0066 (15)
C370.0607 (16)0.056 (2)0.0534 (18)0.0045 (14)0.0071 (14)0.0182 (16)
C380.0513 (16)0.0441 (18)0.076 (2)0.0000 (13)0.0015 (15)0.0173 (17)
C390.0391 (13)0.0434 (18)0.078 (2)0.0013 (12)0.0110 (14)0.0025 (16)
C400.0349 (12)0.0421 (17)0.0497 (17)0.0046 (11)0.0065 (12)0.0061 (14)
C410.0534 (16)0.0418 (17)0.0538 (19)0.0029 (13)0.0230 (15)0.0035 (15)
C420.0463 (13)0.0345 (15)0.0429 (16)0.0040 (11)0.0125 (12)0.0085 (13)
C430.0541 (15)0.0461 (18)0.0496 (17)0.0006 (13)0.0155 (13)0.0048 (14)
C440.0695 (18)0.0395 (18)0.062 (2)0.0041 (14)0.0153 (15)0.0013 (15)
C450.0615 (16)0.0373 (18)0.073 (2)0.0146 (13)0.0149 (15)0.0038 (15)
C460.0473 (14)0.0411 (17)0.0625 (19)0.0057 (12)0.0148 (13)0.0107 (14)
C470.0434 (13)0.0293 (14)0.0438 (15)0.0015 (11)0.0114 (11)0.0085 (12)
C480.0449 (14)0.0388 (17)0.0537 (17)0.0023 (12)0.0152 (13)0.0092 (13)
C490.0447 (13)0.0330 (15)0.0452 (16)0.0010 (11)0.0173 (12)0.0001 (12)
C500.0447 (13)0.0365 (16)0.0402 (15)0.0008 (12)0.0126 (12)0.0047 (12)
C510.0396 (13)0.0398 (16)0.0417 (15)0.0017 (12)0.0107 (11)0.0012 (13)
C520.0446 (13)0.0345 (15)0.0378 (15)0.0021 (11)0.0132 (12)0.0017 (12)
C530.0441 (13)0.0302 (15)0.0385 (15)0.0020 (11)0.0099 (11)0.0018 (12)
C540.0410 (12)0.0326 (15)0.0391 (15)0.0015 (11)0.0110 (11)0.0005 (12)
C550.0433 (13)0.0377 (16)0.0411 (15)0.0033 (12)0.0116 (11)0.0031 (13)
C560.0494 (15)0.0491 (18)0.0607 (19)0.0084 (13)0.0141 (14)0.0049 (14)
C570.0477 (16)0.069 (2)0.060 (2)0.0134 (14)0.0068 (14)0.0000 (17)
C580.0437 (15)0.081 (2)0.0511 (19)0.0006 (15)0.0039 (13)0.0053 (17)
C590.0556 (16)0.0553 (19)0.0451 (17)0.0032 (14)0.0065 (13)0.0103 (14)
C600.0468 (14)0.0416 (17)0.0359 (15)0.0014 (12)0.0077 (12)0.0020 (13)
C610.0544 (15)0.0363 (16)0.0381 (16)0.0004 (12)0.0098 (12)0.0035 (13)
C620.0439 (14)0.0572 (19)0.0432 (17)0.0035 (13)0.0097 (13)0.0041 (14)
C630.0490 (15)0.0465 (17)0.0412 (16)0.0106 (13)0.0118 (12)0.0005 (13)
C640.0530 (15)0.067 (2)0.0444 (17)0.0185 (15)0.0061 (13)0.0002 (15)
C650.0689 (19)0.063 (2)0.067 (2)0.0283 (16)0.0184 (17)0.0078 (17)
C660.079 (2)0.0478 (19)0.072 (2)0.0239 (16)0.0221 (18)0.0035 (16)
C670.0564 (15)0.0445 (18)0.0618 (19)0.0145 (13)0.0151 (14)0.0030 (15)
C680.0473 (14)0.0402 (16)0.0406 (15)0.0107 (12)0.0151 (12)0.0003 (13)
Geometric parameters (Å, º) top
O1—C61.407 (3)C24—H240.9300
O1—C71.372 (3)C25—H250.9300
O2—C71.184 (4)C30—H300.9300
O3—C141.223 (3)C31—H310.9300
O4—C271.212 (3)C32—H320.9300
O5—C281.217 (3)C33—H330.9300
O6—C401.405 (3)C35—C361.387 (4)
O6—C411.364 (3)C35—C401.382 (3)
O7—C411.200 (3)C35—C501.491 (3)
O8—C481.214 (3)C36—C371.382 (4)
O9—C611.219 (3)C37—C381.366 (4)
O10—C621.213 (3)C38—C391.384 (4)
C1—C161.493 (3)C39—C401.367 (4)
C1—C61.381 (4)C41—C421.502 (4)
C1—C21.382 (4)C42—C431.396 (3)
C2—C31.401 (5)C42—C471.400 (3)
C3—C41.382 (5)C43—C441.371 (4)
C4—C51.356 (5)C44—C451.374 (4)
C5—C61.374 (4)C45—C461.370 (4)
C7—C81.495 (4)C46—C471.393 (3)
C8—C131.386 (4)C47—C481.489 (3)
C8—C91.386 (4)C48—C491.507 (3)
C9—C101.366 (5)C49—C501.413 (3)
C10—C111.363 (5)C49—C541.396 (3)
C11—C121.375 (4)C50—C511.378 (3)
C12—C131.396 (4)C51—C521.411 (3)
C13—C141.480 (4)C51—C621.505 (4)
C14—C151.509 (3)C52—C531.385 (3)
C15—C201.392 (3)C52—C681.484 (3)
C15—C161.415 (3)C53—C541.414 (3)
C16—C171.385 (3)C53—C611.500 (3)
C17—C281.496 (3)C54—C551.485 (3)
C17—C181.412 (3)C55—C561.390 (3)
C18—C191.384 (3)C55—C601.391 (3)
C18—C341.491 (3)C56—C571.391 (4)
C19—C271.499 (3)C57—C581.364 (4)
C19—C201.417 (3)C58—C591.381 (4)
C20—C211.493 (3)C59—C601.381 (4)
C21—C221.391 (4)C60—C611.486 (4)
C21—C261.387 (3)C62—C631.486 (4)
C22—C231.393 (4)C63—C641.379 (4)
C23—C241.365 (4)C63—C681.391 (3)
C24—C251.384 (4)C64—C651.376 (4)
C25—C261.379 (4)C65—C661.381 (4)
C26—C271.487 (4)C66—C671.386 (4)
C28—C291.481 (4)C67—C681.376 (4)
C29—C301.377 (4)C36—H360.9300
C29—C341.397 (3)C37—H370.9300
C30—C311.371 (4)C38—H380.9300
C31—C321.380 (4)C39—H390.9300
C32—C331.397 (4)C43—H430.9300
C33—C341.384 (3)C44—H440.9300
C2—H20.9300C45—H450.9300
C3—H30.9300C46—H460.9300
C4—H40.9300C56—H560.9300
C5—H50.9300C57—H570.9300
C9—H90.9300C58—H580.9300
C10—H100.9300C59—H590.9300
C11—H110.9300C64—H640.9300
C12—H120.9300C65—H650.9300
C22—H220.9300C66—H660.9300
C23—H230.9300C67—H670.9300
C6—O1—C7119.8 (2)C34—C33—H33121.00
C40—O6—C41118.32 (19)C36—C35—C40117.6 (2)
C2—C1—C6117.7 (3)C36—C35—C50124.1 (2)
C6—C1—C16118.7 (2)C40—C35—C50118.3 (2)
C2—C1—C16123.5 (3)C35—C36—C37120.4 (2)
C1—C2—C3119.9 (3)C36—C37—C38120.3 (3)
C2—C3—C4119.5 (3)C37—C38—C39120.5 (2)
C3—C4—C5121.5 (3)C38—C39—C40118.4 (2)
C4—C5—C6117.9 (3)O6—C40—C35117.1 (2)
O1—C6—C1116.9 (2)O6—C40—C39120.0 (2)
C1—C6—C5123.5 (3)C35—C40—C39122.8 (2)
O1—C6—C5119.4 (2)O6—C41—O7118.8 (2)
O1—C7—C8115.4 (2)O6—C41—C42117.4 (2)
O2—C7—C8126.7 (3)O7—C41—C42123.2 (2)
O1—C7—O2117.5 (2)C41—C42—C43113.4 (2)
C7—C8—C9114.1 (3)C41—C42—C47127.3 (2)
C9—C8—C13119.6 (3)C43—C42—C47119.3 (2)
C7—C8—C13126.2 (2)C42—C43—C44120.9 (2)
C8—C9—C10120.6 (3)C43—C44—C45120.1 (2)
C9—C10—C11120.3 (3)C44—C45—C46119.7 (2)
C10—C11—C12120.4 (3)C45—C46—C47121.8 (2)
C11—C12—C13120.3 (3)C42—C47—C46118.2 (2)
C8—C13—C12118.9 (2)C42—C47—C48125.6 (2)
C12—C13—C14115.6 (2)C46—C47—C48116.3 (2)
C8—C13—C14125.5 (2)O8—C48—C47120.1 (2)
O3—C14—C13119.3 (2)O8—C48—C49118.8 (2)
C13—C14—C15124.9 (2)C47—C48—C49121.1 (2)
O3—C14—C15115.8 (2)C48—C49—C50119.7 (2)
C14—C15—C20119.5 (2)C48—C49—C54121.1 (2)
C16—C15—C20119.0 (2)C50—C49—C54119.2 (2)
C14—C15—C16120.9 (2)C35—C50—C49118.5 (2)
C1—C16—C17120.0 (2)C35—C50—C51122.5 (2)
C15—C16—C17118.8 (2)C49—C50—C51118.9 (2)
C1—C16—C15121.1 (2)C50—C51—C52122.8 (2)
C16—C17—C28129.3 (2)C50—C51—C62129.1 (2)
C18—C17—C28108.1 (2)C52—C51—C62108.1 (2)
C16—C17—C18122.7 (2)C51—C52—C53118.1 (2)
C17—C18—C19118.3 (2)C51—C52—C68108.5 (2)
C19—C18—C34133.3 (2)C53—C52—C68133.4 (2)
C17—C18—C34108.4 (2)C52—C53—C54120.1 (2)
C18—C19—C20119.8 (2)C52—C53—C61132.1 (2)
C20—C19—C27108.3 (2)C54—C53—C61107.9 (2)
C18—C19—C27132.0 (2)C49—C54—C53120.8 (2)
C15—C20—C21130.3 (2)C49—C54—C55130.5 (2)
C19—C20—C21108.3 (2)C53—C54—C55108.6 (2)
C15—C20—C19121.4 (2)C54—C55—C56132.4 (2)
C20—C21—C22132.7 (2)C54—C55—C60108.3 (2)
C20—C21—C26108.1 (2)C56—C55—C60119.3 (2)
C22—C21—C26119.1 (2)C55—C56—C57118.1 (2)
C21—C22—C23117.9 (2)C56—C57—C58121.9 (2)
C22—C23—C24122.5 (3)C57—C58—C59120.8 (3)
C23—C24—C25120.0 (2)C58—C59—C60117.9 (2)
C24—C25—C26118.1 (2)C55—C60—C59122.1 (2)
C21—C26—C25122.5 (2)C55—C60—C61109.5 (2)
C21—C26—C27110.1 (2)C59—C60—C61128.4 (2)
C25—C26—C27127.4 (2)O9—C61—C53128.1 (2)
O4—C27—C19128.0 (2)O9—C61—C60126.4 (2)
O4—C27—C26126.9 (2)C53—C61—C60105.4 (2)
C19—C27—C26105.1 (2)O10—C62—C51127.0 (2)
O5—C28—C29126.9 (2)O10—C62—C63127.8 (2)
C17—C28—C29105.9 (2)C51—C62—C63105.2 (2)
O5—C28—C17127.2 (2)C62—C63—C64128.8 (2)
C28—C29—C30128.9 (2)C62—C63—C68109.6 (2)
C30—C29—C34121.8 (2)C64—C63—C68121.6 (2)
C28—C29—C34109.3 (2)C63—C64—C65118.5 (2)
C29—C30—C31118.2 (2)C64—C65—C66120.0 (3)
C30—C31—C32121.0 (2)C65—C66—C67121.7 (3)
C31—C32—C33121.3 (2)C66—C67—C68118.3 (2)
C32—C33—C34117.9 (2)C52—C68—C63108.6 (2)
C18—C34—C29108.3 (2)C52—C68—C67131.6 (2)
C29—C34—C33119.8 (2)C63—C68—C67119.8 (2)
C18—C34—C33131.8 (2)C35—C36—H36120.00
C1—C2—H2120.00C37—C36—H36120.00
C3—C2—H2120.00C36—C37—H37120.00
C4—C3—H3120.00C38—C37—H37120.00
C2—C3—H3120.00C37—C38—H38120.00
C5—C4—H4119.00C39—C38—H38120.00
C3—C4—H4119.00C38—C39—H39121.00
C4—C5—H5121.00C40—C39—H39121.00
C6—C5—H5121.00C42—C43—H43120.00
C8—C9—H9120.00C44—C43—H43120.00
C10—C9—H9120.00C43—C44—H44120.00
C11—C10—H10120.00C45—C44—H44120.00
C9—C10—H10120.00C44—C45—H45120.00
C10—C11—H11120.00C46—C45—H45120.00
C12—C11—H11120.00C45—C46—H46119.00
C13—C12—H12120.00C47—C46—H46119.00
C11—C12—H12120.00C55—C56—H56121.00
C21—C22—H22121.00C57—C56—H56121.00
C23—C22—H22121.00C56—C57—H57119.00
C24—C23—H23119.00C58—C57—H57119.00
C22—C23—H23119.00C57—C58—H58120.00
C23—C24—H24120.00C59—C58—H58120.00
C25—C24—H24120.00C58—C59—H59121.00
C26—C25—H25121.00C60—C59—H59121.00
C24—C25—H25121.00C63—C64—H64121.00
C29—C30—H30121.00C65—C64—H64121.00
C31—C30—H30121.00C64—C65—H65120.00
C32—C31—H31119.00C66—C65—H65120.00
C30—C31—H31119.00C65—C66—H66119.00
C31—C32—H32119.00C67—C66—H66119.00
C33—C32—H32119.00C66—C67—H67121.00
C32—C33—H33121.00C68—C67—H67121.00
C7—O1—C6—C176.7 (3)C30—C31—C32—C330.2 (4)
C7—O1—C6—C5107.8 (3)C31—C32—C33—C340.2 (4)
C6—O1—C7—O2166.9 (2)C32—C33—C34—C18179.5 (2)
C6—O1—C7—C820.1 (3)C32—C33—C34—C290.5 (4)
C40—O6—C41—C4232.3 (3)C50—C35—C40—O65.5 (3)
C41—O6—C40—C3569.9 (3)C50—C35—C40—C39178.5 (2)
C41—O6—C40—C39114.0 (3)C36—C35—C50—C4990.7 (3)
C40—O6—C41—O7156.0 (2)C36—C35—C50—C5193.5 (3)
C16—C1—C6—C5175.9 (2)C40—C35—C50—C4987.4 (3)
C2—C1—C16—C15102.7 (3)C40—C35—C50—C5188.4 (3)
C2—C1—C16—C1779.1 (3)C36—C35—C40—O6176.3 (2)
C16—C1—C6—O10.5 (3)C36—C35—C40—C390.3 (4)
C16—C1—C2—C3175.6 (2)C40—C35—C36—C370.8 (4)
C2—C1—C6—O1175.7 (2)C50—C35—C36—C37178.9 (2)
C2—C1—C6—C50.3 (4)C35—C36—C37—C380.9 (4)
C6—C1—C16—C1581.4 (3)C36—C37—C38—C390.4 (4)
C6—C1—C16—C1796.8 (3)C37—C38—C39—C400.1 (4)
C6—C1—C2—C30.3 (4)C38—C39—C40—O6175.8 (2)
C1—C2—C3—C40.4 (4)C38—C39—C40—C350.1 (4)
C2—C3—C4—C50.4 (5)O6—C41—C42—C4393.9 (3)
C3—C4—C5—C60.4 (5)O6—C41—C42—C4788.4 (3)
C4—C5—C6—C10.3 (4)O7—C41—C42—C4377.4 (3)
C4—C5—C6—O1175.6 (3)O7—C41—C42—C47100.3 (3)
O2—C7—C8—C1398.7 (4)C41—C42—C43—C44176.9 (2)
O1—C7—C8—C992.2 (3)C47—C42—C43—C441.0 (4)
O1—C7—C8—C1389.0 (3)C41—C42—C47—C46177.4 (2)
O2—C7—C8—C980.1 (3)C41—C42—C47—C481.4 (4)
C13—C8—C9—C100.4 (4)C43—C42—C47—C460.2 (3)
C7—C8—C13—C12177.7 (2)C43—C42—C47—C48179.0 (2)
C7—C8—C9—C10179.3 (3)C42—C43—C44—C450.9 (4)
C7—C8—C13—C141.3 (4)C43—C44—C45—C460.0 (4)
C9—C8—C13—C121.1 (4)C44—C45—C46—C470.9 (4)
C9—C8—C13—C14179.9 (2)C45—C46—C47—C420.7 (4)
C8—C9—C10—C111.5 (5)C45—C46—C47—C48178.2 (2)
C9—C10—C11—C121.3 (5)C42—C47—C48—O8172.3 (2)
C10—C11—C12—C130.2 (5)C42—C47—C48—C499.8 (4)
C11—C12—C13—C81.4 (4)C46—C47—C48—O88.8 (4)
C11—C12—C13—C14179.5 (3)C46—C47—C48—C49169.1 (2)
C12—C13—C14—C15173.4 (2)O8—C48—C49—C50104.7 (3)
C12—C13—C14—O37.1 (4)O8—C48—C49—C5474.2 (3)
C8—C13—C14—O3172.0 (2)C47—C48—C49—C5077.4 (3)
C8—C13—C14—C157.5 (4)C47—C48—C49—C54103.8 (3)
O3—C14—C15—C2057.0 (3)C48—C49—C50—C354.8 (3)
C13—C14—C15—C1666.4 (3)C48—C49—C50—C51179.3 (2)
C13—C14—C15—C20122.5 (3)C54—C49—C50—C35176.3 (2)
O3—C14—C15—C16114.1 (3)C54—C49—C50—C510.4 (3)
C14—C15—C20—C19169.2 (2)C48—C49—C54—C53177.8 (2)
C14—C15—C20—C2112.7 (4)C48—C49—C54—C550.7 (4)
C16—C15—C20—C192.1 (3)C50—C49—C54—C533.3 (3)
C14—C15—C16—C112.4 (3)C50—C49—C54—C55178.1 (2)
C14—C15—C16—C17169.4 (2)C35—C50—C51—C52174.9 (2)
C20—C15—C16—C1176.5 (2)C35—C50—C51—C623.5 (4)
C20—C15—C16—C171.8 (3)C49—C50—C51—C520.9 (4)
C16—C15—C20—C21176.0 (2)C49—C50—C51—C62179.3 (2)
C15—C16—C17—C28177.8 (2)C50—C51—C52—C530.7 (3)
C1—C16—C17—C18178.6 (2)C50—C51—C52—C68178.8 (2)
C1—C16—C17—C280.4 (4)C62—C51—C52—C53177.9 (2)
C15—C16—C17—C180.4 (4)C62—C51—C52—C682.5 (3)
C16—C17—C18—C34178.5 (2)C50—C51—C62—O100.0 (4)
C28—C17—C18—C19176.3 (2)C50—C51—C62—C63179.6 (2)
C16—C17—C18—C192.3 (4)C52—C51—C62—O10178.5 (3)
C18—C17—C28—C293.2 (3)C52—C51—C62—C631.8 (3)
C16—C17—C28—O53.2 (4)C51—C52—C53—C543.6 (3)
C16—C17—C28—C29178.4 (2)C51—C52—C53—C61176.0 (2)
C28—C17—C18—C343.0 (3)C68—C52—C53—C54175.8 (2)
C18—C17—C28—O5175.2 (3)C68—C52—C53—C614.6 (5)
C17—C18—C19—C201.9 (3)C51—C52—C68—C632.3 (3)
C17—C18—C19—C27177.0 (2)C51—C52—C68—C67176.5 (3)
C19—C18—C34—C29177.5 (3)C53—C52—C68—C63178.3 (3)
C19—C18—C34—C331.7 (5)C53—C52—C68—C673.0 (5)
C17—C18—C34—C33179.3 (3)C52—C53—C54—C495.0 (3)
C34—C18—C19—C20179.1 (2)C52—C53—C54—C55176.2 (2)
C34—C18—C19—C272.1 (5)C61—C53—C54—C49174.7 (2)
C17—C18—C34—C291.6 (3)C61—C53—C54—C554.2 (3)
C18—C19—C20—C21178.3 (2)C52—C53—C61—O98.4 (4)
C27—C19—C20—C15179.3 (2)C52—C53—C61—C60175.4 (2)
C27—C19—C20—C210.9 (3)C54—C53—C61—O9171.2 (2)
C18—C19—C20—C150.2 (4)C54—C53—C61—C605.1 (3)
C18—C19—C27—O43.8 (5)C49—C54—C55—C563.9 (4)
C18—C19—C27—C26176.9 (2)C49—C54—C55—C60177.1 (2)
C20—C19—C27—O4177.3 (3)C53—C54—C55—C56177.5 (3)
C20—C19—C27—C262.1 (3)C53—C54—C55—C601.6 (3)
C15—C20—C21—C26177.5 (2)C54—C55—C56—C57178.9 (2)
C19—C20—C21—C22178.0 (3)C60—C55—C56—C570.1 (4)
C15—C20—C21—C220.3 (5)C54—C55—C60—C59179.4 (2)
C19—C20—C21—C260.8 (3)C54—C55—C60—C611.7 (3)
C20—C21—C26—C272.2 (3)C56—C55—C60—C590.2 (4)
C22—C21—C26—C27179.8 (2)C56—C55—C60—C61179.1 (2)
C26—C21—C22—C230.8 (4)C55—C56—C57—C580.6 (4)
C22—C21—C26—C250.4 (4)C56—C57—C58—C591.6 (4)
C20—C21—C22—C23176.2 (3)C57—C58—C59—C601.8 (4)
C20—C21—C26—C25177.3 (2)C58—C59—C60—C551.1 (4)
C21—C22—C23—C240.4 (4)C58—C59—C60—C61179.8 (2)
C22—C23—C24—C250.4 (4)C55—C60—C61—O9172.2 (2)
C23—C24—C25—C260.8 (4)C55—C60—C61—C534.1 (3)
C24—C25—C26—C210.4 (4)C59—C60—C61—O96.7 (4)
C24—C25—C26—C27179.0 (2)C59—C60—C61—C53177.0 (2)
C21—C26—C27—C192.6 (3)O10—C62—C63—C642.3 (5)
C25—C26—C27—O43.9 (4)O10—C62—C63—C68179.9 (3)
C21—C26—C27—O4176.7 (3)C51—C62—C63—C64177.4 (2)
C25—C26—C27—C19176.8 (2)C51—C62—C63—C680.4 (3)
C17—C28—C29—C342.2 (3)C62—C63—C64—C65177.1 (3)
C17—C28—C29—C30178.5 (2)C68—C63—C64—C650.5 (4)
O5—C28—C29—C303.1 (4)C62—C63—C68—C521.1 (3)
O5—C28—C29—C34176.2 (3)C62—C63—C68—C67177.9 (2)
C34—C29—C30—C310.3 (4)C64—C63—C68—C52179.1 (2)
C28—C29—C34—C180.4 (3)C64—C63—C68—C670.2 (4)
C28—C29—C34—C33178.8 (2)C63—C64—C65—C660.4 (4)
C28—C29—C30—C31179.0 (3)C64—C65—C66—C670.1 (4)
C30—C29—C34—C18179.8 (2)C65—C66—C67—C680.5 (4)
C30—C29—C34—C330.6 (4)C66—C67—C68—C52178.3 (3)
C29—C30—C31—C320.1 (4)C66—C67—C68—C630.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O30.932.372.693 (3)100
C22—H22···O30.932.503.081 (3)121
C24—H24···O10i0.932.563.302 (3)137
C30—H30···O5ii0.932.603.507 (3)166
C32—H32···O7iii0.932.493.398 (3)166
C33—H33···O40.932.323.087 (3)139
C39—H39···O1iv0.932.363.115 (3)139
C46—H46···O80.932.402.728 (3)101
C56—H56···O80.932.523.210 (3)131
C58—H58···O7v0.932.523.377 (3)154
C67—H67···O90.932.363.117 (3)139
Symmetry codes: (i) x+2, y, z+1; (ii) x, y+1, z+2; (iii) x1, y, z; (iv) x+1, y1, z; (v) x+1, y, z+2.

Experimental details

Crystal data
Chemical formulaC34H16O5
Mr504.47
Crystal system, space groupTriclinic, 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)
V3)2382.5 (12)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.28 × 0.18 × 0.14
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.980, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
38137, 10895, 4858
Rint0.061
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.135, 0.94
No. of reflections10895
No. of parameters704
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C24—H24···O10i0.932.563.302 (3)137.
C30—H30···O5ii0.932.603.507 (3)166.
C32—H32···O7iii0.932.493.398 (3)166.
C33—H33···O40.932.323.087 (3)139.
C39—H39···O1iv0.932.363.115 (3)139.
C56—H56···O80.932.523.210 (3)131.
C58—H58···O7v0.932.523.377 (3)154.
C67—H67···O90.932.363.117 (3)139.
Symmetry codes: (i) x+2, y, z+1; (ii) x, y+1, z+2; (iii) x1, y, z; (iv) x+1, y1, 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

First citationAltomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339–340.  Web of Science CrossRef CAS IUCr Journals
First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
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First citationJin, M.-C., Cai, M.-Q. & Chen, X.-H. (2009). J. Anal. Toxicol. 33, 294–300.  Web of Science CrossRef PubMed CAS
First citationSeniutinas, G., Tomasiunas, R., Czapilicki, R., Sahraoui, B., Daskeviciene, M., Getaut, V. & Balveicius, Z. (2012). Dyes Pigm. 95, 33–40.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals
First citationZargar, N. D. & Khan, K. Z. (2012). Global J. Sci. Frontier Res. B, XII, 45–48.

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Volume 68| Part 12| December 2012| Pages o3363-o3364
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