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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 12| December 2013| Pages o1822-o1823

Benzene-1,3,5-triyl tribenzoate

aDepartment of Chemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA
*Correspondence e-mail: pcorfield@fordham.edu

(Received 8 November 2013; accepted 18 November 2013; online 27 November 2013)

The title compound, C27H18O6, commonly known as phloroglucinol tribenzoate, is a standard unit for the family of benzyl ether dendrimers. The central phloroglucinol residue is close to planar, with out-of-plane distances for the three oxygen atoms of up to 0.095 (3) Å, while the three attached benzoate groups are approximately planar. One benzoate group is twisted [C—C—O—C torsion angle = 98.2 (3)°] from the central plane, with its carbonyl O atom 2.226 (4) Å above that plane, while the other two benzoate groups are twisted in the opposite direction [C—C—O—C torsion angles = 24.7 (2) and 54.8 (2)°], so that their carbonyl O atoms are on the other side of, and closer to the central plane, with distances from the plane of 1.743 (4) and 1.206 (4) Å. One benzoate group is disordered between two conformers, with occupancies of 86.9 (3) and 13.1 (3)%, related by a 143 (1)° rotation about the bond to the central benzene ring. The phenyl groups of the two conformers occupy the same space. The mol­ecule packs in the crystal with two of the three benzoate phenyl rings stacked parallel to symmetry-related counterparts, with perpendicular distances of 3.715 (5) and 3.791 (5) Å. The parallel rings are slipped away from each other, however, with centroid–centroid distances of 4.122 (2) and 4.363 (2) Å, respectively.

Related literature

For a review of structural features of specific dendrimers, see: Stadler (2010[Stadler, A.-M. (2010). Cryst. Growth Des. 10, 5050-5065.]). For related crystal structures, see: Pigge et al. (2010[Pigge, F. C., Vangala, V. R., Swenson, D. C. & Rath, N. P. (2010). Cryst. Growth Des. 10, 224-231.]); Shi & Zhang (2006[Shi, J. & Zhang, Z.-T. (2006). Z. Kristallogr. 221, 176-178.]); Sasvari & Parkanyi (1980[Sasvari, K. & Parkanyi, L. (1980). Cryst. Struct. Commun. 9, 277-280.]). For related papers on the properties and synthesis of dendrimers, see: Monaco et al. (2013[Monaco, D. N., Tomas, S. C., Kirrane, M. K. & Balija, A. M. (2013). Beilstein J. Org. Chem. 9, 2320-2327.]); Moore & Stupp (1990[Moore, J. S. & Stupp, S. I. (1990). Macromolecules, 23, 65-70.]); Nagvekar & Gibson (1997[Nagvekar, D. S. & Gibson, H. W. (1997). Org. Prep. Proced. Int. 29, 240-242.]).

[Scheme 1]

Experimental

Crystal data
  • C27H18O6

  • Mr = 438.41

  • Monoclinic, P 21 /c

  • a = 23.128 (5) Å

  • b = 6.332 (2) Å

  • c = 15.030 (3) Å

  • β = 103.22 (2)°

  • V = 2142.8 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 295 K

  • 0.4 × 0.4 × 0.13 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • 4950 measured reflections

  • 3775 independent reflections

  • 2096 reflections with I > 2σ(I)

  • Rint = 0.021

  • 3 standard reflections every 120 min intensity decay: 0.5 (4)%

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.114

  • S = 1.03

  • 3775 reflections

  • 295 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.16 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction followed procedures in Corfield et al. (1973[Corfield, P. W. R., Dabrowiak, J. C. & Gore, E. S. (1973). Inorg. Chem. 12, 1734-1740.]) and data were averaged with a local version of SORTAV (Blessing, 1989[Blessing, R. H. (1989). J. Appl. Cryst. 22, 396-397.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA..]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Dendrimers are macromolecules whose composition and molecular weights are well defined. The present work is part of a systematic study examining how functional groups within a dendrimer family influence the ability to remove small organic pollutants from an aqueous environment (Monaco et al. 2013). The title compound is a model for larger dendrimer systems.

The central phloroglucinol residue is close to planar, with out-of-plane distances for the three oxygen atoms varying up to 0.09 Å. Deviations from planarity for the three benzoate groups are larger, with the carbonyl groups twisting to make their oxygen atoms 0.3–0.4 Å from the planes of the phenyl groups (see Fig.1). The benzoate group (C16–C21,C8,O5) is twisted approximately perpendicular to the central plane, with torsional angle C2–C3–O2–C8 = 98.2 (3)°, forcing its carbonyl oxygen atom 2.226 (4) Å Above the central plane. The other two benzoate groups are twisted less, and in the opposite sense, with torsional angles C6–C1–O1–C7 = -125.2 (2) and C4–C5–O3–C9A = -146.3 (2)°, and carbonyl oxygen atoms on the other side of and closer to the central plane. Similar torsional angles were observed in one of the two similar molecules in Shi and Zhang (2006), and in Sasvari and Parkanyi (1980).

Fig. 2 shows the packing of the phloroglucinol tribenzoate molecules in the crystal. There may be some interactions between aromatic rings C10–C15 and C16–C21 and their parallel counterparts related by centers of symmetry at 1/2,1/2,1/2 and 0,0,1/2. The perpendicular distances between the planes of the symmetry related rings are 3.715 (5) Å and 3.791 (5) Å respectively. There are few close contacts between the parallel rings, however, as the rings are slipped from direct opposition by 1.78 and 2.15 Å respectively. Indeed the shortest intermolecular contacts in the crystal occur between hydrogen atoms on parallel rings displaced by one unit cell in the direction of the b axis: H21.. H21 (-x,1 - y,1 - z) = 2.32 Å and H11.. H11(1 - x,-y,1 - z) = 2.74 Å. The disordered benzoate does not show any interaction between parallel phenyl rings.

Related literature top

For a review of structural features of specific dendrimers, see: Stadler (2010). For related crystal structures, see: Pigge et al. (2010); Shi & Zhang (2006); Sasvari & Parkanyi (1980). For related papers on the properties and synthesis of dendrimers, see: Monaco et al. (2013); Moore & Stupp (1990); Nagvekar & Gibson (1997).

Experimental top

The synthesis described below was performed under an argon gas atmosphere with oven dried glassware. Reagents were obtained from Aldrich. The reagent 2-(dimethylamino)pyridinium p-toluenesulfonate (DPTS) was synthesized as reported previously (Moore et al., 1990). Solvents and reagents were used without further purification except for the following: dichloromethane was distilled from CaH2 and phloroglucinol dihydrate was azeotroped 5 times with toluene prior to use. Eluent solvent ratios are reported in v/v.

1H NMR spectra were recorded at 300 MHz and 13C NMR spectra were recorded at 75 MHz on a Bruker AV-300 High Performance Digital NMR Spectrometer. Chemical shifts are reported in parts per million (p.p.m.) and coupling constants are reported in Hertz (Hz). 1H NMR spectra obtained in CDCl3 were referenced to 7.26 p.p.m. and 13C NMR spectra obtained in CDCl3 were referenced to 77.2 p.p.m.. Mass spectra were obtained from the University of Illinois Mass Spectrometry Center (Micromass Q-Tof Ultra, ESI).

The preparation of phloroglucinol tribenzoate was performed as follows: To a solution of 0.25 g (2.05 mmol) of benzoic acid in 10 ml of dichloromethane was added 0.08 g (0.62 mmol) of phloroglucinol, 0.47 g (2.26 mmol) of N,N'-dicyclohexylcarbodiimide, and 0.63 g (2.26 mmol) of DPTS. The reaction was stirred overnight, filtered, and washed with cold dichloromethane. After the solvent was removed in vacuo, the resulting material was purified by silica gel column chromatography (gradient system 2:1 petroleum ether:dichloromethane 1:1 petroleum ether:dichloromethane) to obtain 0.16 g (58% yield) of the product as a white solid. 1H NMR (CDCl3): σ 8.22 (d, J = 7.1, 6H), 7.67 (tt, J = 7.4, 1.6, 3H), 7.54 (t, J = 7.6, 6H), 7.19 (s, 3H). 13C NMR (CDCl3): σ 164.6, 151.8, 134.1, 130.4, 129.2, 128.9, 113.5. MS-ESI: m/z [M + Na+K]+2: 500.3. Spectral data were similar to previously reported data (Nagvekar et al., 1997). Single crystals appeared upon slow evaporation of a solution of phloroglucinol tribenzoate in dichloromethane.

Refinement top

Refinements with anisotropic temperature factors for C and O atoms and constrained hydrogen atom parameters converged smoothly to R(F2>2σ)=0.0563 for 299 variables.

The difference Fourier synthesis at this point showed two peaks of 0.78 and 0.55 e Å3 in the vicinity of the ester oxygen O3, with no other peak above 0.21 e Å3. We have interpreted these two peaks with a partially disordered structure in which the benzoate group O3–C9A(–O6)-(C22–C27) is rotated 149 (1)° about C5–O3 so that C9B and O6B, alternatives to C9A and O6A, fit on the two peaks. The rotated ring C22B–C27B occupies the same space as the original C22A–C27A ring. The relationship of the disordered rings is illustrated in Fig. 3.

In final refinements modeling this disorder, the bond lengths for O3—C9B and C9B—C27B were constrained, to avoid their refinement to unreasonable values. The disordered phenyl group C22B—C27B was constrained to a rigid hexagon with bond lengths 1.378 Å, a value chosen from results of refinements where this distance was increased incrementally. Joint anisotropic temperature factors were assigned for corresponding carbon atoms in the disordered phenyl groups. Atom O6B was allowed to vibrate anisotropically. To reduce the number of parameters varied, the benzoate phenyl groups C10—C15 and C16—C21 were also constrained as rigid hexagons. With these constraints, refinement converged with R(F2>2σ)=0.0401 for 295 variables. Occupancy factors for the disordered groups are 86.9 (3)% and 13.1 (3)%. The new final difference Fourier synthesis showed no peaks above 0.16 e Å3. Use of further restraints on distances in the disordered benzoate group did not improve the geometry.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: data reduction followed procedures in Corfield et al. (1973); data were averaged with a local version of SORTAV (Blessing, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The ORTEPIII drawing of the phloroglucinol tribenzoate molecule, with ellipsoids at the 50% level. The view is perpendicular to the central phenyl group, atoms C1–C6. Only the major component of the disordered benzoate group is shown, with atoms labeled A.
[Figure 2] Fig. 2. Packing diagram for the phloroglucinol tribenzoate structure, showing how two of the benzoate phenyl groups stack around centers of symmetry at (0,0,1/2) and (1/2,1/2,1/2). The molecule at (x,y,z) is boldly outlined. Ellipsoids are at the 30% level.
[Figure 3] Fig. 3. Part of the molecule of phloroglucinol tribenzoate, showing the disordered benzoate group.
Benzene-1,3,5-triyl tribenzoate top
Crystal data top
C27H18O6F(000) = 912
Mr = 438.41Dx = 1.359 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 23.128 (5) Åθ = 3.6–20.3°
b = 6.332 (2) ŵ = 0.10 mm1
c = 15.030 (3) ÅT = 295 K
β = 103.22 (2)°Plate cut from large crystal, colourless
V = 2142.8 (9) Å30.4 × 0.4 × 0.13 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.8°
Graphite monochromatorh = 2726
θ/2θ scansk = 07
4950 measured reflectionsl = 017
3775 independent reflections3 standard reflections every 120 min
2096 reflections with I > 2σ(I) intensity decay: 0.5(4)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 w = 1/[σ2(Fo2) + (0.P)2 + 0.450P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.114(Δ/σ)max < 0.001
S = 1.03Δρmax = 0.15 e Å3
3775 reflectionsΔρmin = 0.16 e Å3
295 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0067 (7)
Primary atom site location: structure-invariant direct methods
Crystal data top
C27H18O6V = 2142.8 (9) Å3
Mr = 438.41Z = 4
Monoclinic, P21/cMo Kα radiation
a = 23.128 (5) ŵ = 0.10 mm1
b = 6.332 (2) ÅT = 295 K
c = 15.030 (3) Å0.4 × 0.4 × 0.13 mm
β = 103.22 (2)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.021
4950 measured reflections3 standard reflections every 120 min
3775 independent reflections intensity decay: 0.5(4)
2096 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0402 restraints
wR(F2) = 0.114H-atom parameters constrained
S = 1.03Δρmax = 0.15 e Å3
3775 reflectionsΔρmin = 0.16 e Å3
295 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.

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
xyzUiso*/UeqOcc. (<1)
O10.35661 (7)0.5340 (3)0.49441 (10)0.0470 (4)
O20.15556 (7)0.3414 (3)0.35077 (11)0.0486 (4)
O30.24069 (7)0.9621 (3)0.25815 (12)0.0538 (5)
O40.37050 (8)0.2080 (3)0.44526 (14)0.0740 (6)
O50.11874 (8)0.5541 (3)0.44322 (14)0.0719 (6)
C10.30356 (10)0.5610 (4)0.42800 (15)0.0405 (6)
C20.25623 (10)0.4259 (4)0.42122 (16)0.0438 (6)
H20.25900.30500.45710.053*
C30.20481 (10)0.4767 (4)0.35957 (16)0.0421 (6)
C40.19981 (10)0.6514 (4)0.30364 (16)0.0436 (6)
H40.16460.68090.26140.052*
C50.24860 (10)0.7809 (4)0.31228 (15)0.0416 (6)
C60.30092 (10)0.7405 (4)0.37541 (15)0.0429 (6)
H60.33330.83120.38220.051*
C70.38779 (10)0.3519 (4)0.49572 (17)0.0455 (6)
C80.11408 (10)0.3985 (4)0.39679 (17)0.0466 (6)
C100.44494 (5)0.3584 (3)0.56490 (10)0.0428 (6)
C110.47896 (7)0.1775 (2)0.57685 (11)0.0577 (7)
H110.46460.05500.54530.069*
C120.53426 (7)0.1781 (3)0.63561 (13)0.0669 (8)
H120.55720.05600.64370.080*
C130.55554 (6)0.3595 (3)0.68242 (11)0.0650 (8)
H130.59290.35990.72210.078*
C140.52152 (7)0.5404 (3)0.67047 (11)0.0642 (8)
H140.53590.66290.70210.077*
C150.46622 (7)0.5399 (2)0.61171 (12)0.0551 (7)
H150.44330.66200.60360.066*
C160.06392 (6)0.2479 (2)0.38278 (11)0.0440 (6)
C170.06666 (6)0.0496 (3)0.34617 (11)0.0513 (7)
H170.10110.00560.32960.062*
C180.01834 (8)0.0835 (2)0.33404 (12)0.0607 (8)
H180.02020.21730.30930.073*
C190.03272 (7)0.0183 (3)0.35852 (13)0.0720 (9)
H190.06530.10810.35030.086*
C200.03546 (6)0.1800 (3)0.39513 (13)0.0749 (9)
H200.06990.22390.41160.090*
C210.01286 (7)0.3131 (2)0.40725 (12)0.0599 (8)
H210.01100.44690.43200.072*
C22A0.26207 (19)1.2348 (5)0.1664 (2)0.0428 (10)0.869 (3)
C23A0.30488 (14)1.3733 (8)0.1497 (2)0.0522 (9)0.869 (3)
H23A0.34491.34610.17380.063*0.869 (3)
C24A0.2879 (2)1.5522 (7)0.0970 (3)0.0608 (9)0.869 (3)
H24A0.31651.64710.08720.073*0.869 (3)
C25A0.2294 (3)1.5889 (6)0.0596 (3)0.0573 (9)0.869 (3)
H25A0.21831.70810.02360.069*0.869 (3)
C26A0.18673 (18)1.4519 (10)0.0746 (3)0.0561 (9)0.869 (3)
H26A0.14701.47740.04780.067*0.869 (3)
C27A0.20245 (17)1.2766 (7)0.1291 (3)0.0487 (10)0.869 (3)
H27A0.17331.18660.14080.058*0.869 (3)
C9A0.28368 (12)1.0471 (5)0.22254 (18)0.0428 (7)0.869 (3)
O6A0.33266 (8)0.9761 (4)0.23489 (14)0.0620 (7)0.869 (3)
C27B0.2213 (18)1.234 (3)0.1497 (18)0.0487 (10)0.131 (3)
C22B0.2801 (15)1.294 (4)0.1727 (14)0.0428 (10)0.131 (3)
H22B0.30761.21250.21320.051*0.131 (3)
C23B0.2982 (8)1.475 (5)0.136 (2)0.0522 (9)0.131 (3)
H23B0.33791.51490.15110.063*0.131 (3)
C24B0.2575 (17)1.595 (3)0.0756 (18)0.0608 (9)0.131 (3)
H24B0.26971.71730.05060.073*0.131 (3)
C25B0.1986 (14)1.536 (4)0.0526 (14)0.0573 (9)0.131 (3)
H25B0.17111.61740.01210.069*0.131 (3)
C26B0.1805 (8)1.355 (5)0.090 (2)0.0561 (9)0.131 (3)
H26B0.14081.31500.07420.067*0.131 (3)
O6B0.1535 (6)0.978 (2)0.1877 (11)0.077 (5)0.131 (3)
C9B0.1998 (8)1.048 (3)0.1964 (12)0.059 (6)*0.131 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0475 (9)0.0382 (10)0.0499 (10)0.0048 (8)0.0003 (8)0.0000 (8)
O20.0472 (9)0.0429 (10)0.0581 (10)0.0123 (9)0.0169 (8)0.0070 (9)
O30.0517 (10)0.0453 (11)0.0634 (11)0.0024 (9)0.0110 (9)0.0177 (9)
O40.0591 (12)0.0552 (13)0.0993 (16)0.0053 (10)0.0007 (11)0.0290 (12)
O50.0679 (12)0.0612 (13)0.0925 (15)0.0157 (10)0.0308 (11)0.0328 (12)
C10.0396 (13)0.0417 (15)0.0382 (13)0.0046 (11)0.0044 (10)0.0013 (12)
C20.0507 (15)0.0372 (14)0.0445 (13)0.0026 (12)0.0130 (11)0.0032 (12)
C30.0413 (13)0.0388 (14)0.0464 (14)0.0048 (12)0.0106 (11)0.0036 (12)
C40.0388 (13)0.0474 (15)0.0432 (14)0.0005 (12)0.0064 (10)0.0012 (13)
C50.0421 (14)0.0372 (14)0.0458 (14)0.0020 (11)0.0104 (11)0.0058 (12)
C60.0429 (13)0.0395 (15)0.0457 (13)0.0029 (12)0.0091 (11)0.0012 (12)
C70.0461 (14)0.0397 (15)0.0522 (15)0.0017 (13)0.0141 (12)0.0001 (13)
C80.0441 (14)0.0472 (17)0.0472 (14)0.0001 (12)0.0075 (12)0.0017 (13)
C100.0406 (13)0.0410 (15)0.0482 (14)0.0024 (12)0.0128 (11)0.0026 (12)
C110.0518 (16)0.0458 (17)0.0748 (19)0.0068 (13)0.0128 (14)0.0017 (15)
C120.0577 (18)0.060 (2)0.080 (2)0.0194 (16)0.0112 (15)0.0102 (17)
C130.0492 (16)0.082 (2)0.0601 (17)0.0045 (17)0.0057 (14)0.0026 (17)
C140.0582 (17)0.062 (2)0.0667 (18)0.0016 (16)0.0022 (14)0.0092 (16)
C150.0545 (16)0.0495 (17)0.0576 (16)0.0083 (14)0.0051 (13)0.0015 (14)
C160.0443 (14)0.0437 (16)0.0423 (13)0.0037 (12)0.0065 (11)0.0015 (12)
C170.0471 (15)0.0463 (17)0.0584 (16)0.0013 (13)0.0076 (12)0.0043 (14)
C180.0631 (18)0.0492 (18)0.0644 (18)0.0142 (15)0.0033 (15)0.0014 (15)
C190.0600 (18)0.080 (2)0.074 (2)0.0318 (18)0.0125 (15)0.0009 (18)
C200.0544 (17)0.091 (3)0.085 (2)0.0153 (18)0.0282 (16)0.002 (2)
C210.0575 (16)0.0639 (19)0.0622 (17)0.0062 (15)0.0220 (14)0.0067 (15)
C22A0.052 (3)0.038 (2)0.0378 (14)0.0008 (15)0.0095 (14)0.0018 (14)
C23A0.0564 (19)0.047 (2)0.0508 (18)0.006 (2)0.0064 (15)0.0091 (19)
C24A0.073 (3)0.048 (2)0.059 (2)0.010 (2)0.010 (2)0.0138 (18)
C25A0.075 (3)0.045 (2)0.0516 (18)0.0102 (19)0.015 (2)0.0108 (16)
C26A0.0589 (18)0.058 (3)0.0516 (19)0.0195 (19)0.0123 (15)0.004 (2)
C27A0.049 (2)0.0471 (19)0.052 (2)0.0086 (18)0.0165 (19)0.0037 (17)
C9A0.0424 (16)0.0424 (17)0.0438 (16)0.0015 (15)0.0103 (13)0.0017 (14)
O6A0.0471 (13)0.0663 (16)0.0751 (15)0.0141 (11)0.0191 (11)0.0256 (12)
C27B0.049 (2)0.0471 (19)0.052 (2)0.0086 (18)0.0165 (19)0.0037 (17)
C22B0.052 (3)0.038 (2)0.0378 (14)0.0008 (15)0.0095 (14)0.0018 (14)
C23B0.0564 (19)0.047 (2)0.0508 (18)0.006 (2)0.0064 (15)0.0091 (19)
C24B0.073 (3)0.048 (2)0.059 (2)0.010 (2)0.010 (2)0.0138 (18)
C25B0.075 (3)0.045 (2)0.0516 (18)0.0102 (19)0.015 (2)0.0108 (16)
C26B0.0589 (18)0.058 (3)0.0516 (19)0.0195 (19)0.0123 (15)0.004 (2)
O6B0.042 (8)0.069 (11)0.119 (13)0.003 (8)0.017 (8)0.032 (10)
Geometric parameters (Å, º) top
O1—C71.357 (3)C17—H170.9300
O1—C11.404 (3)C18—C191.3780
O2—C81.354 (3)C18—H180.9300
O2—C31.407 (3)C19—C201.3780
O3—C9B1.285 (15)C19—H190.9300
O3—C51.394 (3)C20—C211.3780
O3—C9A1.345 (3)C20—H200.9300
O4—C71.194 (3)C21—H210.9300
O5—C81.198 (3)C22A—C23A1.388 (4)
C1—C61.378 (3)C22A—C27A1.390 (4)
C1—C21.374 (3)C22A—C9A1.477 (4)
C2—C31.368 (3)C23A—C24A1.386 (4)
C2—H20.9300C23A—H23A0.9300
C3—C41.378 (3)C24A—C25A1.362 (5)
C4—C51.377 (3)C24A—H24A0.9300
C4—H40.9300C25A—C26A1.371 (5)
C5—C61.380 (3)C25A—H25A0.9300
C6—H60.9300C26A—C27A1.378 (5)
C7—C101.484 (3)C26A—H26A0.9300
C8—C161.479 (3)C27A—H27A0.9300
C10—C111.3780C9A—O6A1.193 (3)
C10—C151.3781C27B—C22B1.3780
C11—C121.3780C27B—C26B1.3781
C11—H110.9300C27B—C9B1.514 (16)
C12—C131.3780C22B—C23B1.3780
C12—H120.9300C22B—H22B0.9300
C13—C141.3780C23B—C24B1.3780
C13—H130.9300C23B—H23B0.9300
C14—C151.3781C24B—C25B1.3780
C14—H140.9300C24B—H24B0.9300
C15—H150.9300C25B—C26B1.3780
C16—C171.3780C25B—H25B0.9300
C16—C211.3781C26B—H26B0.9300
C17—C181.3780O6B—C9B1.14 (2)
C7—O1—C1119.26 (19)C19—C18—H18120.0
C8—O2—C3116.22 (19)C17—C18—H18120.0
C9B—O3—C5138.3 (9)C20—C19—C18120.0
C9B—O3—C9A91.9 (8)C20—C19—H19120.0
C5—O3—C9A123.5 (2)C18—C19—H19120.0
C6—C1—C2122.7 (2)C21—C20—C19120.0
C6—C1—O1115.2 (2)C21—C20—H20120.0
C2—C1—O1121.9 (2)C19—C20—H20120.0
C1—C2—C3117.3 (2)C20—C21—C16120.0
C1—C2—H2121.4C20—C21—H21120.0
C3—C2—H2121.4C16—C21—H21120.0
C4—C3—C2122.7 (2)C23A—C22A—C27A119.3 (3)
C4—C3—O2118.6 (2)C23A—C22A—C9A116.7 (4)
C2—C3—O2118.7 (2)C27A—C22A—C9A124.0 (4)
C3—C4—C5117.9 (2)C22A—C23A—C24A120.0 (3)
C3—C4—H4121.1C22A—C23A—H23A120.0
C5—C4—H4121.1C24A—C23A—H23A120.0
C4—C5—C6121.7 (2)C25A—C24A—C23A120.0 (3)
C4—C5—O3116.1 (2)C25A—C24A—H24A120.0
C6—C5—O3122.1 (2)C23A—C24A—H24A120.0
C1—C6—C5117.7 (2)C24A—C25A—C26A120.6 (3)
C1—C6—H6121.2C24A—C25A—H25A119.7
C5—C6—H6121.2C26A—C25A—H25A119.7
O4—C7—O1122.6 (2)C25A—C26A—C27A120.3 (3)
O4—C7—C10125.5 (2)C25A—C26A—H26A119.8
O1—C7—C10111.8 (2)C27A—C26A—H26A119.8
O5—C8—O2122.5 (2)C22A—C27A—C26A119.7 (3)
O5—C8—C16125.2 (2)C22A—C27A—H27A120.1
O2—C8—C16112.3 (2)C26A—C27A—H27A120.1
C11—C10—C15120.0O6A—C9A—O3123.3 (3)
C11—C10—C7117.32 (15)O6A—C9A—C22A125.3 (3)
C15—C10—C7122.53 (15)O3—C9A—C22A111.4 (3)
C12—C11—C10120.0C22B—C27B—C26B120.0
C12—C11—H11120.0C22B—C27B—C9B121 (3)
C10—C11—H11120.0C26B—C27B—C9B119 (3)
C11—C12—C13120.0C27B—C22B—C23B120.0
C11—C12—H12120.0C27B—C22B—H22B120.0
C13—C12—H12120.0C23B—C22B—H22B120.0
C12—C13—C14120.0C24B—C23B—C22B120.0
C12—C13—H13120.0C24B—C23B—H23B120.0
C14—C13—H13120.0C22B—C23B—H23B120.0
C15—C14—C13120.0C25B—C24B—C23B120.0
C15—C14—H14120.0C25B—C24B—H24B120.0
C13—C14—H14120.0C23B—C24B—H24B120.0
C14—C15—C10120.0C24B—C25B—C26B120.0
C14—C15—H15120.0C24B—C25B—H25B120.0
C10—C15—H15120.0C26B—C25B—H25B120.0
C17—C16—C21120.0C25B—C26B—C27B120.0
C17—C16—C8122.56 (15)C25B—C26B—H26B120.0
C21—C16—C8117.44 (15)C27B—C26B—H26B120.0
C16—C17—C18120.0O6B—C9B—O3115.8 (15)
C16—C17—H17120.0O6B—C9B—C27B131 (2)
C18—C17—H17120.0O3—C9B—C27B114 (2)
C19—C18—C17120.0
C6—C1—O1—C7125.2 (2)C4—C5—O3—C9A146.3 (2)
C1—O1—C7—O43.8 (4)C4—C5—O3—C9B3.1 (15)
C1—O1—C7—C10175.05 (18)C5—O3—C9A—O6A0.8 (4)
O1—C7—C10—C11175.99 (15)C5—O3—C9A—C22A178.6 (2)
O1—C7—C10—C158.5 (2)C5—O3—C9B—O6B12 (3)
C2—C3—O2—C898.2 (3)C5—O3—C9B—C22B169.2 (9)
C3—O2—C8—O50.6 (3)O3—C9A—C22A—C23A160.5 (3)
C3—O2—C8—C16179.54 (18)O3—C9A—C22A—C27A20.7 (4)
O2—C8—C16—C1714.8 (3)O3—C9B—C27B—C26B172.6 (13)
O2—C8—C16—C21164.75 (15)O3—C9B—C27B—C22B2 (2)

Experimental details

Crystal data
Chemical formulaC27H18O6
Mr438.41
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)23.128 (5), 6.332 (2), 15.030 (3)
β (°) 103.22 (2)
V3)2142.8 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.4 × 0.4 × 0.13
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4950, 3775, 2096
Rint0.021
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.114, 1.03
No. of reflections3775
No. of parameters295
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.15, 0.16

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), data reduction followed procedures in Corfield et al. (1973); data were averaged with a local version of SORTAV (Blessing, 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

 

Acknowledgements

We are grateful to the Office of the Dean at Fordham University for its generous financial support. We thank Fordham University students Sarah C. Tomas and Olivia N. Monaco for assistance with this work. The Q-Tof Ultima mass spectrometer (University of Illinois at Urbana-Champaign) was purchased in part with a grant from the NSF, Division of Biological Infrastructure (DBI-0100085).

References

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Volume 69| Part 12| December 2013| Pages o1822-o1823
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