Dibenzo-18-crown-6–picric acid–water (1/2/3) Muhammad Idiris Saleh, a Eny Kusrini, a Mohd Mustaqim Rosli b and Hoong-Kun Fun b * a School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and b X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia Correspondence e-mail: hkfun@usm.my Received 16 June 2008; accepted 18 June 2008 Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.004 A ˚ ; R factor = 0.044; wR factor = 0.110; data-to-parameter ratio = 9.9. In the crown ether ring of the title compound, C 20 H 24 O 6 - 2C 6 H 3 N 3 O 7 3H 2 O, the O—C(H 2 )—C(H 2 )—O torsion angles indicate a gauche conformation of the ethyleneoxy units, while the C—O—C—C torsion angles indicate planarity of these segments; the dihedral angle between the two benzene rings is 44.53 (13) . In both picric acid molecules, one of the nitro groups is twisted away from the attached ring. The molecules are linked into chains along the b axis via intermolecular O— HO hydrogen bonds. In addition, the crystal structure is stabilized by C—HO hydrogen bonds and – interactions [centroid–centroid distance between benzene rings = 3.5697 (16) A ˚ ]. Related literature For bond-length data, see: Allen et al. (1987). For related literature, see: Bush & Truter (1971); Colquhoun et al. (1986); Kanters et al. (1986); Lu et al. (1993a,b); Robinson et al. (1987); Saleh et al. (1996, 1997); You et al. (2002); Zhou et al. (1996). Experimental Crystal data C 20 H 24 O 6 2C 6 H 3 N 3 O 7 3H 2 O M r = 872.67 Orthorhombic, Pna2 1 a = 16.4192 (2) A ˚ b = 7.0845 (1) A ˚ c = 31.4135 (4) A ˚ V = 3654.08 (8) A ˚ 3 Z =4 Mo K radiation = 0.14 mm 1 T = 100.0 (1) K 0.36 0.32 0.16 mm Data collection Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005) T min = 0.952, T max = 0.979 37248 measured reflections 5431 independent reflections 4559 reflections with I >2(I) R int = 0.045 Refinement R[F 2 >2(F 2 )] = 0.044 wR(F 2 ) = 0.110 S = 1.06 5431 reflections 550 parameters 1 restraint H-atom parameters constrained Á max = 0.40 e A ˚ 3 Á min = 0.33 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ , ). D—HA D—H HA DA D—HA O7—H1O7O3W 1.00 1.92 2.618 (3) 124 O7—H1O7O13 1.00 1.84 2.664 (3) 138 O7—H1O7N3 1.00 2.49 2.985 (3) 110 O1W—H1W1O6 0.87 2.14 2.978 (3) 162 O1W—H2W1O2W 0.94 2.03 2.900 (4) 152 O2W—H1W2O1 i 0.85 2.56 3.215 (3) 135 O2W—H1W2O2 i 0.85 2.45 3.265 (3) 162 O2W—H2W2O4 i 0.85 2.42 3.198 (3) 152 O2W—H2W2O5 i 0.85 2.43 3.155 (3) 144 O3W—H1W3O3 0.85 2.02 2.861 (3) 173 O3W—H2W3O1W 0.95 1.96 2.881 (3) 163 O14—H14BO1W 0.78 2.06 2.732 (3) 144 O14—H14BO20 0.78 2.05 2.632 (3) 131 C3—H3AO11 ii 0.93 2.60 3.323 (4) 136 C7—H7AO6 iii 0.97 2.58 3.393 (3) 142 C7—H7BO19 iv 0.97 2.59 3.135 (4) 116 C9—H9AO12 iii 0.97 2.39 3.341 (4) 165 C19—H19AO19 v 0.97 2.53 3.301 (3) 137 Symmetry codes: (i) x; y þ 1; z; (ii) x þ 1 2 ; y 1 2 ; z þ 1 2 ; (iii) x 1 2 ; y þ 1 2 ; z; (iv) x; y 1; z; (v) x þ 1 2 ; y þ 1 2 ; z. Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003). The authors thank the Malaysian Government and Universiti Sains Malaysia for providing SAGA (No. 304/ PKIMIA/653010/A118) and FRGS (No.203/PKIMIA/671020) research grants. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2617). organic compounds o1318 Saleh et al. doi:10.1107/S1600536808018485 Acta Cryst. (2008). E64, o1318–o1319 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368