(4-Cyano­phenolato)(subphthalocyaninato)boronElectron-withdrawing groups in the para position of the phen­oxy mol­ecular fragment. Part 3. For Part 1, see: Paton et al. (2010b); for Part 2, see: Paton et al. (2011).

Paton, A.S.; Lough, A.J.; Bender, T.P.

doi:10.1107/S1600536811000869

Volume 67
Part 2
Pages o505-o506
February 2011

Received 29 October 2010
Accepted 6 January 2011
Online 29 January 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R = 0.049
wR = 0.141
Data-to-parameter ratio = 16.4
Details

(4-Cyanophenolato)(subphthalocyaninato)boron¹

Andrew S. Paton,^a Alan J. Lough ^b and Timothy P. Bender ^a ^*

^aDepartment of Chemical Engineering & Applied Chemistry, University of Toronto, 200 College Street, Toronto, Ontario, Canada M5S 3E5, and ^bDepartment of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6
Correspondence e-mail: tim.bender@utoronto.ca

The crystal structure of the title compound, C₃₁H₁₆BN₇O, (CNPhO-BsubPc) is characterized by pairs of [pi] - [pi] stacking interactions between the concave faces of inversion-related BsubPc fragments with a centroid-centroid distance of 3.600 (1) Å. In addition, these pairs of molecules are linked into chains along [101] through further weak [pi] - [pi] stacking interactions with a centroid-centroid distance of 3.8587 (9) Å. There are also weak C-H [pi] (arene) interactions within the chains.

Related literature

For a general review of boronsubphthalocyanine compounds (BsubPcs), see: Claessens et al. (2002). For the synthesis of boronsubphthalocyanine and its derivatives, see: Zyskowski & Kennedy (2000); Claessens et al. (2003); Paton et al. (2011b). For the application of BsubPcs in organic electronic devices, see: Morse et al. (2010) and references cited therein; Gommans et al. (2009). For related crystal structures of non-halogenated boronsubphthalocyanine derivatives, see: Potz et al. (2000); Paton et al. (2010, 2011a,b). For the treatment of disordered solvent molecules, see: Athimoolam et al. (2005); Cox et al. (2003); Mohamed et al. (2003); Stähler et al. (2001).

Experimental

Crystal data

C₃₁H₁₆BN₇O
M_r = 513.32
Monoclinic, C 2/c
a = 16.2310 (3) Å
b = 27.5129 (7) Å
c = 13.4385 (2) Å
= 119.4050 (12)°
V = 5228.00 (18) Å³
Z = 8
Mo K radiation
= 0.08 mm^-1
T = 150 K
0.40 × 0.30 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.711, T_max = 0.994
21404 measured reflections
5914 independent reflections
4290 reflections with I > 2(I)
R_int = 0.087

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.141
S = 1.06
5914 reflections
361 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C25-C30, N1/C1/C2/C7/C8 and N3/C9/C10/C15/C19 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C3-H3ACg1ⁱ	0.95	2.70	3.499 (3)	143
C20-H20ACg2ⁱⁱ	0.95	2.59	3.254 (4)	127
C21-H21ACg3ⁱⁱ	0.95	2.70	3.238 (4)	116
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2323 ).

Acknowledgements

We wish to acknowledge funding for this research from the Natural Sciences and Engineering Research Council (NSERC) of Canada.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Athimoolam, S., Kumar, J., Ramakrishnan, V. & Rajaram, R. K. (2005). Acta Cryst. E61, m2014-m2017.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Claessens, C. G., González-Rodríguez, D., del Rey, B. & Torres, T. (2002). Chem. Rev. 102, 835-853.
Claessens, C. G., González-Rodríguez, D., del Rey, B., Torres, T., Mark, G., Schuchmann, H.-P., von Sonntag, C., MacDonald, J. G. & Nohr, R. S. (2003). Eur. J. Org. Chem. pp. 2547-2551.
Cox, P. J., Kumarasamy, Y., Nahar, L., Sarker, S. D. & Shoeb, M. (2003). Acta Cryst. E59, o975-o977.
Gommans, H., Aernouts, T., Verreet, B., Heremans, P., Medina, A., Claessens, C. G. & Torres, T. (2009). Adv. Funct. Mater. 19, 3435-3439.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Mohamed, A. A., Krause Bauer, J. A., Bruce, A. E. & Bruce, M. R. M. (2003). Acta Cryst. C59, m84-m86.
Morse, G. E., Helander, M. G., Maka, J. F., Lu, Z. H. & Bender, T. P. (2010). Appl. Mater. Inter. 2, 1934-1944.
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Paton, A. S., Lough, A. J. & Bender, T. P. (2010). Acta Cryst. E66, o3246.
Paton, A. S., Lough, A. J. & Bender, T. P. (2011a). Acta Cryst. E67, o57.
Paton, A. S., Morse, G. E., Lough, A. J. & Bender, T. P. (2011b). CrystEngComm, 13, 914-919.
Potz, R., Goldner, M., Huckstadt, H., Cornelissen, U., Tutass, A. & Homborg, H. (2000). Z. Anorg. Allg. Chem. 626, 588-596.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Stähler, R., Näther, C. & Bensch, W. (2001). Acta Cryst. C57, 26-27.
Zyskowski, C. D. & Kennedy, V. O. (2000). J. Porphyrins Phthalocyanins, pp. 707-712.