1,2-Bis[(3,5-diphenyl-1H-pyrazol-1-yl)- methyl]benzene Lara C. Spencer, a Ilia A. Guzei, a,b * Tebogo V. Segapelo b and James Darkwa b a Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA, and b Department of Chemistry, University of Johannes- burg, Auckland Park Kingsway Campus, Johannesburg 2006, South Africa Correspondence e-mail: iguzei@chem.wisc.edu Received 5 July 2012; accepted 19 July 2012 Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 A ˚ ; R factor = 0.035; wR factor = 0.094; data-to-parameter ratio = 14.1. The title compound, C 38 H 30 N 4 , a potentially mono- and bidentate ligand, does not seem to form palladium complexes similar to other poly(pyrazol-1-ylmethyl)benzenes due to the large steric size of the phenyl substituents on the pyrazole rings. The pyrazole rings have a 21.09 (5)  angle between their mean planes and exhibit a trans-like geometry in which the in- plane lone pairs of electrons on the 2-N nitrogen atoms point in opposite directions. Related literature For information about poly(pyrazol-1-ylmethyl)benzenes and the metal complexes they form, see: Hartshorn & Steel (1995, 1997, 1998); Motsoane et al. (2007). For information on the related compounds 1,2-bis[(3-(2,2 0 -bipyridin-6-yl)pyrazol-1- yl)methyl]benzene and 2,3-bis[(3-(2-pyridyl)pyrazol-1-yl)- methyl]naphthalene, see: Al-Rasbi et al. (2007); Paul et al. (2003). Geometrical parameters were checked with Mogul (Bruno et al. , 2002). Experimental Crystal data C 38 H 30 N 4 M r = 542.66 Monoclinic, P2 1 =c a = 14.5338 (2) A ˚ b = 13.6779 (2) A ˚ c = 15.0051 (2) A ˚  = 110.102 (1)  V = 2801.18 (7) A ˚ 3 Z =4 Cu K radiation  = 0.59 mm 1 T = 100 K 0.25  0.18  0.15 mm Data collection Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007) T min = 0.891, T max = 0.943 44869 measured reflections 5337 independent reflections 4496 reflections with I >2(I) R int = 0.033 Refinement R[F 2 >2(F 2 )] = 0.035 wR(F 2 ) = 0.094 S = 1.00 5337 reflections 379 parameters H-atom parameters constrained Á max = 0.22 e A ˚ 3 Á min = 0.21 e A ˚ 3 Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL and FCF_filter (Guzei, 2007); molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL, publCIF (Westrip, 2010) and ModiCIFer (Guzei, 2007). The authors would like to thank the University of Johan- nesburg for support. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2175). References Al-Rasbi, N. K., Adams, H., Harding, L. P. & Ward, M. D. (2007). Eur. J. Inorg. Chem. pp. 4770–4780. Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Bruker (2007). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Bruno, I. J., Cole, J. C., Edgington, P. R., Kessler, M., Macrae, C. F., McCabe, P., Pearson, J. & Taylor, R. (2002). Acta Cryst. B58, 389–397. Guzei, I. A. (2007). In-house Crystallographic Programs: FCF_filter and ModiCIFer. Molecular Structure Laboratory, University of Wisconsin– Madison, Madison, Wisconsin, USA. Hartshorn, M. C. & Steel, P. J. (1995). Aust. J. Chem. 48, 1587–1599. Hartshorn, M. C. & Steel, P. J. (1997). Chem. Commun. pp. 541–542. Hartshorn, M. C. & Steel, P. J. (1998). Organometallics, 17, 3487–3496. Motsoane, N. M., Guzei, I. A.& Darkwa, J. (2007). Z. Naturforsch. Teil B, 60, 323-330. Paul, R. L., Bell, Z. R.,Jeffery, J. C., Harding, L. P., McCleverty, J. A. & Ward, M. D. (2003). Polyhedron, 22, 781–787. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. organic compounds o2584 Spencer et al. doi:10.1107/S1600536812032801 Acta Cryst. (2012). E68, o2584 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368