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Volume 69 
Part 12 
Pages o1822-o1823  
December 2013  

Received 8 November 2013
Accepted 18 November 2013
Online 27 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.040
wR = 0.114
Data-to-parameter ratio = 12.8
Details
Open access

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

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

  • [beta] = 103.22 (2)°

  • V = 2142.8 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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 > 2[sigma](I)

  • Rint = 0.021

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

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.114

  • S = 1.03

  • 3775 reflections

  • 295 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2503 ).


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

Blessing, R. H. (1989). J. Appl. Cryst. 22, 396-397.  [CrossRef] [IUCr Journals]
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA..
Corfield, P. W. R., Dabrowiak, J. C. & Gore, E. S. (1973). Inorg. Chem. 12, 1734-1740.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Monaco, D. N., Tomas, S. C., Kirrane, M. K. & Balija, A. M. (2013). Beilstein J. Org. Chem. 9, 2320-2327.  [CrossRef]
Moore, J. S. & Stupp, S. I. (1990). Macromolecules, 23, 65-70.  [CrossRef] [ChemPort] [Web of Science]
Nagvekar, D. S. & Gibson, H. W. (1997). Org. Prep. Proced. Int. 29, 240-242.  [CrossRef] [ChemPort]
Pigge, F. C., Vangala, V. R., Swenson, D. C. & Rath, N. P. (2010). Cryst. Growth Des. 10, 224-231.  [CSD] [CrossRef] [ChemPort]
Sasvari, K. & Parkanyi, L. (1980). Cryst. Struct. Commun. 9, 277-280.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Shi, J. & Zhang, Z.-T. (2006). Z. Kristallogr. 221, 176-178.  [ChemPort]
Stadler, A.-M. (2010). Cryst. Growth Des. 10, 5050-5065.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1822-o1823   [ doi:10.1107/S1600536813031462 ]

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