1,8-Diazabicyclo[5.4.0]undec-7-en-8- ium bromido(phthalocyaninato)zincate Bartosz Przybyl and Jan Janczak* Institute of Low Temperature and Structural Research, Polish Academy of Sciences, Oko ´ lna 2, Wroclaw, 50-422, Poland Correspondence e-mail: j.janczak@int.pan.wroc.pl Received 24 April 2014; accepted 19 May 2014 Key indicators: single-crystal X-ray study; T = 295 K; mean (C–C) = 0.006 A ˚ ; R factor = 0.057; wR factor = 0.143; data-to-parameter ratio = 17.8. The title compound, (C 9 H 17 N 2 )[ZnBr(C 32 H 16 N 8 )], contains a bromido(phthalocyaninato)zincate anion and a protonated 1,8-diazabicyclo[5.4.0]undece-7-ene cation, [DBUH] + . The central Zn II atom has a distorted square-pyramidal geometry, with four isoindole N atoms of the macrocycle in equatorial positions and a bromide ion in the axial position. The latter has a relatively high displacement parameter, but no evidence for disorder was obtained. The central Zn II atom is displaced by 0.488 (3) A ˚ from the mean plane defined by the four isoindole N atoms. The [DBUH] + cation is involved in an almost linear N—HBr hydrogen bond. In the crystal, – interactions lead to a relatively short distance of 3.366 (3) A ˚ between the phthalocyaninate rings. Related literature For background information on phthalocyanines, see: Nyokong et al. (1987); Gregory (2000); Leznoff & Lever (1996); Tedesco et al. (2003); Ormond & Freeman (2013). For related structures, see: Kobayashi et al. (1971); Mossoyan- Deneux et al. (1985); Zeng et al. (2005); Del Sole et al. (2005); Kubiak et al. (2007); Yang et al. (2008); Janczak et al. (2009, 2011); Janczak & Kubiak (2009); Li et al. (2011); Przybyl & Janczak (2014). Experimental Crystal data (C 9 H 17 N 2 )[ZnBr(C 32 H 16 N 8 )] M r = 811.05 Monoclinic, P2 1 =n a = 12.4336 (8) A ˚ b = 22.9278 (16) A ˚ c = 13.3267 (9) A ˚ = 113.266 (4) V = 3490.2 (4) A ˚ 3 Z =4 Mo K radiation = 1.90 mm 1 T = 295 K 0.35 0.21 0.19 mm Data collection Kuma KM-4 with CCD detector diffractometer Absorption correction: numerical (CrysAlis RED; Oxford Diffrac- tion, 2008) T min = 0.562, T max = 0.725 42041 measured reflections 8492 independent reflections 4908 reflections with I >2(I) R int = 0.045 Refinement R[F 2 >2(F 2 )] = 0.057 wR(F 2 ) = 0.143 S = 1.00 8492 reflections 478 parameters H atoms treated by a mixture of independent and constrained refinement Á max = 0.76 e A ˚ 3 Á min = 1.26 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—HA D—H HA DA D—HA N10—H10Br1 0.87 (2) 2.44 (2) 3.281 (4) 163 (2) Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduc- tion: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXL97. This work was supported by the Ministry of Science and Higher Education (grant No. N N204 397540). Supporting information for this paper is available from the IUCr electronic archives (Reference: FJ2673). References Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Del Sole, R., De Luca, A., Mele, G. & Vasapollo, G. (2005). J. Porphyrins Phthalocyanines, 9, 519–527. Gregory, P. (2000). J. Porphyrins Phthalocyanines, 4, 432–437. Janczak, J. & Kubiak, R. (2009). Polyhedron, 28, 2391–2396. Janczak, J., Kubiak, R. & Bukowska, E. (2009). J. Mol. Struct. 937, 25–33. Janczak, J., Kubiak, R. & Lisowski, J. (2011). Polyhedron, 30, 253–258. Kobayashi, T., Ashida, W., Uyeda, N., Suito, E. & Makudo, M. (1971). Bull. Chem. Soc. Jpn, 44, 2095–2103. Kubiak, R., Janczak, J., S ´ ledz ´, M. & Bukowska, E. (2007). Polyhedron, 26, 4179–4186. Li, X., He, X., Chen, Y., Fan, X. & Zeng, Q. (2011). J. Mol. Struct. 1002, 145– 150. Leznoff, C. C. & Lever, A. B. P. (1996). Editors. Phthalocyanines: Properties and Applications, Vol. 4. New York: VCH Publishers. Mossoyan-Deneux, M., Benlian, D., Pierrot, M., Fournel, A. & Sorbier, J. P. (1985). Inorg. Chem. 24, 1878–1882. metal-organic compounds Acta Cryst. (2014). E70, m231–m232 doi:10.1107/S160053681401157X Przybyl and Janczak m231 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368