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

Pansuriya, P.B.; Friedrich, H.B.; Maguire, G.E.M.

doi:10.1107/S1600536811051567

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 (C-C) = 0.006 Å
R = 0.056
wR = 0.162
Data-to-parameter ratio = 10.0
Details

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

Pramod B. Pansuriya,^a Holger B. Friedrich ^a and Glenn E. M. Maguire ^a ^*

^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 C_2v `boat' geometry and there are a range of C-HO contacts in the crystal structure.

Related literature

For applications of resorcin[4]arenes, see: Ajami et al. (2011); Sun et al. (2010); Arnott et al. (2006); Sokoliess et al. (2002). For structural information, see: Wiegmann & Mattay (2011); Pansuriya et al. (2011). For details of C-H [pi] interactions, see: Nishio (2004). For the synthesis of tetramethoxy resorcin[4]arenes: Mclldowie et al. (2000).

Experimental

Crystal data

C₇₆H₈₀O₁₆
M_r = 1249.40
Monoclinic, P 2₁
a = 14.1361 (7) Å
b = 32.2264 (17) Å
c = 28.9417 (16) Å
= 90.572 (1)°
V = 13183.9 (12) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.965, T_max = 0.975
126671 measured reflections
33391 independent reflections
23289 reflections with I > 2(I)
R_int = 0.072

Refinement

R[F² > 2(F²)] = 0.056
wR(F²) = 0.162
S = 1.02
33391 reflections
3345 parameters
1 restraint
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C14B-H14BO16Aⁱ	1.00	2.59	3.440 (4)	142
C30B-H30CO11Aⁱ	0.99	2.49	3.464 (6)	169
C30C-H30FO8Dⁱⁱ	0.99	2.55	3.259 (4)	128
C30D-H30GO8Cⁱⁱⁱ	0.99	2.56	3.270 (5)	129
C44A-H44BO10B^iv	0.98	2.54	3.292 (5)	133
C56C-H56HO7B^v	0.98	2.55	3.375 (9)	141
C56D-H56KO15A^vi	0.98	2.37	3.251 (8)	149
C62C-H62CO7C^vii	0.95	2.46	3.313 (6)	149
C62D-H62DO7D^vii	0.95	2.59	3.421 (7)	146
C63A-H63AO3B^viii	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); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); 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.
Arnott, G., Hunter, R. & Su, H. (2006). Tetrahedron, 62, 977-991.
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.
Mclldowie, M. J., Mocerino, M., Skelton, B. W. & White, A. H. (2000). Org. Lett. 2, 3869-3871.
Nishio, M. (2004). CrystEngComm, 6, 130-158.
Pansuriya, P. B., Friedrich, H. B. & Maguire, G. E. M. (2011). Acta Cryst. E67, o2565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sokoliess, T., Menyes, U., Roth, U. & Jira, T. (2002). J. Chromatogr. A, 948, 309-319.
Sun, Y., Yong, Y., Yan, C., Han, Y. & Shen, M. (2010). ACS NANO, 4, 2129-2141.
Wiegmann, S. & Mattay, J. (2011). Org. Lett. 13, 3226-3228.

organic compounds