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Volume 69 
Part 5 
Page o680  
May 2013  

Received 21 March 2013
Accepted 27 March 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.039
wR = 0.100
Data-to-parameter ratio = 18.4
Details
Open access

2,2',2''-[(2,4,6-Trimethoxybenzene-1,3,5-triyl)tris(methylene)]tris(isoindole-1,3-dione)

aInstitut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
Correspondence e-mail: monika.mazik@chemie.tu-freiberg.de

The title molecule, C36H27N3O9, adopts an almost symmetric conformation in which the mean planes of the phthalimido units are inclined at dihedral angles of 81.1 (1), 85.3 (1) and 86.3 (1)° with respect to the plane of the central aromatic ring. The O atoms are involved in intra- and intermolecular C-H...O hydrogen bonding. The crystal structure also features [pi]-[pi] arene interactions [minimum ring centroid separation = 3.683 (2) Å]. The present mode of non-covalent interactions leads to a three-dimensional supramolecular architecture.

Related literature

For hydrogen bonds in the solid state, see: Desiraju (2002[Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.]); Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural Chemistry and Biology. IUCR Monographs on Crystallography, Vol. 9. New York: Oxford University Press.]); Steiner (2002[Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.]). For C-H...O hydrogen bonds in ketones carrying a terminal pyridine subunit, see: Mazik et al. (2001[Mazik, M., Bläser, D. & Boese, R. (2001). Tetrahedron, 57, 5791-5797.]). For a review on acyclic receptors based on a benzene-derived core, see: Mazik (2009[Mazik, M. (2009). Chem. Soc. Rev. 38, 935-956.]).

[Scheme 1]

Experimental

Crystal data
  • C36H27N3O9

  • Mr = 645.61

  • Triclinic, [P \overline 1]

  • a = 10.2370 (3) Å

  • b = 10.3671 (3) Å

  • c = 14.6501 (4) Å

  • [alpha] = 79.804 (1)°

  • [beta] = 79.512 (1)°

  • [gamma] = 83.874 (1)°

  • V = 1500.20 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.51 × 0.50 × 0.28 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.949, Tmax = 0.971

  • 29692 measured reflections

  • 8026 independent reflections

  • 6992 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.100

  • S = 0.96

  • 8026 reflections

  • 436 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7A...O8i 0.98 2.47 3.2068 (15) 132
C8-H8B...O5i 0.98 2.34 3.2920 (15) 165
C9-H9A...O4ii 0.98 2.56 3.4742 (15) 156
C9-H9C...O9 0.98 2.38 3.2684 (19) 151
C10-H10A...O4 0.99 2.54 2.9144 (14) 102
C10-H10B...O3 0.99 2.32 2.8017 (15) 109
C19-H19A...O7 0.99 2.54 2.9200 (15) 103
C19-H19B...O2 0.99 2.36 2.8457 (14) 109
C23-H23...O1iii 0.95 2.45 3.3231 (16) 153
C28-H28A...O8 0.99 2.52 2.9187 (16) 103
C28-H28B...O3 0.99 2.34 2.8289 (16) 109
C32-H32...O2iv 0.95 2.56 3.2917 (16) 134
C34-H34...O7v 0.95 2.46 3.4066 (15) 172
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z; (iv) -x+1, -y, -z+1; (v) x, y-1, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2198 ).


References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. (2002). Acc. Chem. Res. 35, 565-573.  [ISI] [CrossRef] [PubMed] [ChemPort]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond In Structural Chemistry and Biology. IUCR Monographs on Crystallography, Vol. 9. New York: Oxford University Press.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Mazik, M. (2009). Chem. Soc. Rev. 38, 935-956.  [ISI] [CrossRef] [PubMed] [ChemPort]
Mazik, M., Bläser, D. & Boese, R. (2001). Tetrahedron, 57, 5791-5797.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48-76.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o680  [ doi:10.1107/S1600536813008428 ]

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