(4-Nitro­phenolato)(subphthalo­cyaninato)boron(III)Electron withdrawing groups in the para position of the phen­oxy mol­ecular fragment. Part 2. For Part 1, see Paton et al. (2010a).

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

doi:10.1107/S1600536810050580

Volume 67
Part 1
Page o57
January 2011

Received 29 October 2010
Accepted 2 December 2010
Online 8 December 2010

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R = 0.049
wR = 0.141
Data-to-parameter ratio = 14.6
Details

(4-Nitrophenolato)(subphthalocyaninato)boron(III)¹

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 main feature of the structure of the title compound, C₃₀H₁₆BN₇O₃ or NO₂PhO-BsubPc, are pairs of molecules linked through [pi] -interactions between the concave faces of the BsubPc fragments at a distance of 3.5430 (11) Å across an inversion centre. However, the angle between the planes of the five- and six-menbered rings involved in this interaction is 1.44 (10)°, causing the interacting BsubPcs units to be slightly askew rather than parallel as is typical for [pi] -stacking interactions.

Related literature

For a general review of boronsubphthalocyanine compounds (BsubPcs), see: Claessens et al. (2002). For synthesis of BsubPcs and their derivatives, see: Zyskowski & Kennedy (2000); Claessens et al. (2003); Paton et al. (2010). For the application of BsubPcs in organic electronic devices, see: Morse et al. (2010) and references cited therein; Gommans et al. (2007). For related structures of non-halogenated BsubPc derivatives, see: Potz et al. (2000); Paton et al. (2010a,b).

Experimental

Crystal data

C₃₀H₁₆BN₇O₃
M_r = 533.31
Monoclinic, P 2₁ /n
a = 15.6597 (4) Å
b = 8.2959 (1) Å
c = 19.5409 (5) Å
= 110.3060 (9)°
V = 2380.82 (9) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 150 K
0.40 × 0.26 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.786, T_max = 1.000
19982 measured reflections
5413 independent reflections
3646 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.049
wR(F²) = 0.141
S = 1.03
5413 reflections
371 parameters
H-atom parameters constrained
_max = 0.27 e Å^-3
_min = -0.33 e Å^-3

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); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2204 ).

Acknowledgements

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

References

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