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Volume 68 
Part 1 
Pages o97-o98  
January 2012  

Received 27 October 2011
Accepted 30 November 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.006 Å
R = 0.056
wR = 0.162
Data-to-parameter ratio = 10.0
Details
Open access

6,12,18,24-Tetramethoxy-4,10,16,22-tetrakis[(methoxycarbonyl)methoxy]-2,8,14,20-tetrakis(2-phenylethyl)resorcin[4]arene

aSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa
Correspondence e-mail: maguireg@ukzn.ac.za

The title compound, C76H80O16, is a macrocyclic structure. This novel resorcin[4]arene derivative has (methoxycarbonyl)methoxy `head' groups on the upper rim. The compound has a C2v `boat' geometry and there are a range of C-H...O contacts in the crystal structure.

Related literature

For applications of resorcin[4]arenes, see: Ajami et al. (2011[Ajami, D., Dube, H. & Rebek, J. (2011). J. Am. Chem. Soc. 133, 9689-9691.]); Sun et al. (2010[Sun, Y., Yong, Y., Yan, C., Han, Y. & Shen, M. (2010). ACS NANO, 4, 2129-2141.]); Arnott et al. (2006[Arnott, G., Hunter, R. & Su, H. (2006). Tetrahedron, 62, 977-991.]); Sokoliess et al. (2002[Sokoliess, T., Menyes, U., Roth, U. & Jira, T. (2002). J. Chromatogr. A, 948, 309-319.]). For structural information, see: Wiegmann & Mattay (2011[Wiegmann, S. & Mattay, J. (2011). Org. Lett. 13, 3226-3228.]); Pansuriya et al. (2011[Pansuriya, P. B., Friedrich, H. B. & Maguire, G. E. M. (2011). Acta Cryst. E67, o2565.]). For details of C-H...[pi] interactions, see: Nishio (2004[Nishio, M. (2004). CrystEngComm, 6, 130-158.]). For the synthesis of tetramethoxy resorcin[4]arenes: Mclldowie et al. (2000[Mclldowie, M. J., Mocerino, M., Skelton, B. W. & White, A. H. (2000). Org. Lett. 2, 3869-3871.]).

[Scheme 1]

Experimental

Crystal data
  • C76H80O16

  • Mr = 1249.40

  • Monoclinic, P 21

  • a = 14.1361 (7) Å

  • b = 32.2264 (17) Å

  • c = 28.9417 (16) Å

  • [beta] = 90.572 (1)°

  • V = 13183.9 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.41 × 0.33 × 0.29 mm

Data collection
  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.965, Tmax = 0.975

  • 126671 measured reflections

  • 33391 independent reflections

  • 23289 reflections with I > 2[sigma](I)

  • Rint = 0.072

Refinement
  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.162

  • S = 1.02

  • 33391 reflections

  • 3345 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C14B-H14B...O16Ai 1.00 2.59 3.440 (4) 142
C30B-H30C...O11Ai 0.99 2.49 3.464 (6) 169
C30C-H30F...O8Dii 0.99 2.55 3.259 (4) 128
C30D-H30G...O8Ciii 0.99 2.56 3.270 (5) 129
C44A-H44B...O10Biv 0.98 2.54 3.292 (5) 133
C56C-H56H...O7Bv 0.98 2.55 3.375 (9) 141
C56D-H56K...O15Avi 0.98 2.37 3.251 (8) 149
C62C-H62C...O7Cvii 0.95 2.46 3.313 (6) 149
C62D-H62D...O7Dvii 0.95 2.59 3.421 (7) 146
C63A-H63A...O3Bviii 0.95 2.37 3.267 (7) 156
Symmetry codes: (i) x, y+1, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+2]; (iii) [-x+1, y+{\script{1\over 2}}, -z+2]; (iv) [-x+2, y-{\script{1\over 2}}, -z+1]; (v) [-x+2, y-{\script{1\over 2}}, -z+2]; (vi) [-x+2, y+{\script{1\over 2}}, -z+2]; (vii) x+1, y, z; (viii) x-1, y-1, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5129 ).


Acknowledgements

The authors wish to thank Dr Hong Su from the Chemistry Department of the University of Cape Town for her assistance with the data collection and refinement and the DST - National Research Foundation Centre of Excellence in Catalysis, c*change for financial support. PBP is thankful to the University of KwaZulu-Natal for a postdoctoral fellowship.

References

Ajami, D., Dube, H. & Rebek, J. (2011). J. Am. Chem. Soc. 133, 9689-9691.  [CrossRef] [ChemPort] [PubMed]
Arnott, G., Hunter, R. & Su, H. (2006). Tetrahedron, 62, 977-991.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2006). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Mclldowie, M. J., Mocerino, M., Skelton, B. W. & White, A. H. (2000). Org. Lett. 2, 3869-3871.  [PubMed]
Nishio, M. (2004). CrystEngComm, 6, 130-158.  [ISI] [CrossRef] [ChemPort]
Pansuriya, P. B., Friedrich, H. B. & Maguire, G. E. M. (2011). Acta Cryst. E67, o2565.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sokoliess, T., Menyes, U., Roth, U. & Jira, T. (2002). J. Chromatogr. A, 948, 309-319.  [ISI] [PubMed] [ChemPort]
Sun, Y., Yong, Y., Yan, C., Han, Y. & Shen, M. (2010). ACS NANO, 4, 2129-2141.  [CrossRef] [ChemPort] [PubMed]
Wiegmann, S. & Mattay, J. (2011). Org. Lett. 13, 3226-3228.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o97-o98   [ doi:10.1107/S1600536811051567 ]

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