2 ; y þ 2 ; z þ 2 ; (ii) x þ 2 ; y þ 2 ; z þ 2 ; (iii) x þ 1; y; z.

1. organic compounds Acta Crystallographica Section E Structure Reports Online Experimental Crystal data C8H12N Cl ISSN 1600-5368 A second monoclinic polymorph of 2,4-dimethylanilinium chloride Soudeh Hossein Zadeh,a Mohamad Reza Talei Bavil Olyai,b* Hossein Biglari Mazlaghania and Behrouz Notashc aDepartment of Chemistry, Islamic Azad University, Karaj Branch, Karaj, Iran, bDepartment of Chemistry, Islamic Azad University, South Tehran Branch, Tehran, Iran, and cDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran Correspondence e-mail: talei3@gmail.com Received 14 October 2011; accepted 29 October 2011 Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.002 A˚ ; R factor = 0.042; wR factor = 0.104; data-to-parameter ratio = 21.7. Mr = 157.64 Monoclinic, P21 =n a = 5.3651 (11) A˚ b = 18.631 (4) A˚ c = 8.5428 (17) A˚ = 94.48 (3) Data collection Stoe IPDS 2T diffractometer 5557 measured reflections 2276 independent reflections Refinement R[F 2 > 2 (F 2)] = 0.042 wR(F 2) = 0.104 S = 1.09 2276 reflections 105 parameters Table 1 Hydrogen-bond geometry (A˚ , ). Z = 4 Mo K radiation = 0.38 mm 1 T = 298 K 0.45 0.4 0.34 mm 1838 reflections with I > 2 (I) Rint = 0.031 H atoms treated by a mixture of independent and constrained refinement max = 0.22 e A˚ 3 min = 0.17 e A˚ 3 A second monoclinic polymorph of 2,4-dimethylanilinium + D—H A D—H H A D A D—H A N1—H1A Cl1i 0.91 (2) 2.28 (2) 3.1721 (17) 164.4 (17) chloride, C8H12N Cl , (I), is reported. The unit-cell dimen- N1—H1B Cl1ii 0.88 (2) 2.35 (2) 3.2228 (17) 172.1 (18) iii sions differ from those of the first reported monoclinic form, N1—H1C Cl1 0.94 (2) 2.23 (2) 3.1630 (16) 172.8 (19) (II) [Yao (2010). Acta Cryst. E66, o1563]. Nevertheless, both Symmetry codes: (i) x þ 1 3 1 3 3 1 compounds crystallize in the monoclinic space group P21/n. As in (II), the protonated amine group in (I) acts as a hydrogen- bond donor to the chloride ion, forming three N—H Cl hydrogen bonds. The result is a two-dimensional network in the ac plane. The difference in the hydrogen-bond pattern is that in (I) only 12-membered rings are formed whereas in (II), eight-membered and 16-membered rings are formed. 2; y þ 2; z þ 2; (ii) x þ 2; y þ 2; z þ 2; (iii) x þ 1; y; z. + Related literature For another monoclinic polymorph of the title compound, see: Yao (2010). For properties of compounds containing inorganic anions and organic cations, see: Masse et al. (1993); Xiao et al. (2005). Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X- AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999). The authors wish to acknowledge Islamic Azad University, Karaj Branch for financial support. http://www.kiau.ac.ir Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5679). References Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. Masse, R., Bagieu-Beucher, M., Pecault, J., Levy, J. P. & Zyss, J. (1993). Nonlin. Opt. 5, 413–423. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Stoe & Cie (2005). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Xiao, D., An, H., Wang, E. & Xu, L. (2005). J. Mol. Struct. 738, 217–225. Yao, J.-Y. (2010). Acta Cryst. E66, o1563. o3190 Hossein Zadeh et al. doi:10.1107/S160053681104551X Acta Cryst. (2011). E67, o3190 electronic reprint