organic compounds Acta Crystallographica Section E Z =6 T = 293 K Structure Reports Mo K radiation 0.25 Â 0.24 Â 0.22 mm À1 Online = 0.39 mm ISSN 1600-5368 Data collection Rigaku R-AXIS RAPID 12872 measured reflections diffractometer 5919 independent reflections Pyridine-2-carboximidamidate chloride Absorption correction: multi-scan 4550 reflections with I >2(I) (ABSCOR; Higashi, 1995) Rint = 0.024 monohydrate Tmin = 0.909, Tmax = 0.918 Qifan Chen,a Huidong Zhang,a Fang Zhangb and Fei Liub* Refinement R[F 2 >2(F 2)] = 0.035 418 parameters 2 aExperiment Center, Eastern Liaoning University, No. 325 Wenhua Road, Yuanbao wR(F ) = 0.117 All H-atom parameters refined ˚ À3 District, Dandong City, Liaoning Province 118003, People’s Republic of China, and S = 1.11 Ámax = 0.23 e A À3 b À ˚ College of Chemical Engineering & Materials, Eastern Liaoning University, No. 325 5919 reflections Ámin = 0.26 e A Wenhua Road, Yuanbao District, Dandong City, Liaoning Province 118003, People’s Republic of China Correspondence e-mail: [email protected] Table 1 Hydrogen-bond geometry (A˚ , ). Received 26 October 2010; accepted 9 November 2010 D—HÁÁÁAD—H HÁÁÁADÁÁÁAD—HÁÁÁA Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.003 A˚; N23—H23BÁÁÁO1i 0.87 (2) 1.97 (2) 2.829 (2) 173 (2) R factor = 0.035; wR factor = 0.117; data-to-parameter ratio = 14.2. N22—H22BÁÁÁCl1 0.89 (3) 2.31 (3) 3.187 (2) 169 (2) N12—H12BÁÁÁCl3ii 0.91 (2) 2.35 (2) 3.2522 (19) 170.2 (18) O1—H1BÁÁÁCl3 0.80 (3) 2.37 (3) 3.163 (2) 169 (2) iii The title compound, C H N +ÁClÀÁH O, crystallizes with three N2—H2AÁÁÁCl2 0.85 (3) 2.49 (3) 3.326 (2) 167 (2) 6 8 3 2 O1—H10ÁÁÁCl2iv 0.98 (4) 2.22 (4) 3.1902 (19) 173 (3) formula units in the asymmetric unit. The cations are non- N3—H3AÁÁÁO2 0.87 (2) 1.94 (2) 2.808 (2) 174.9 (19) N2—H2BÁÁÁCl1 0.96 (2) 2.32 (2) 3.2754 (17) 170.9 (17) planar with the –C(NH2)2 groups twisted out of the ring N12—H12AÁÁÁCl3v 0.89 (2) 2.43 (2) 3.313 (2) 171 (2) planes. Each pyridine carboximidamidate cation is linked to N23—H23AÁÁÁCl3vi 0.87 (2) 2.50 (2) 3.324 (2) 158 (2) another cation through N—HÁÁÁN hydrogen bonds, to N13—H13BÁÁÁO3ii 0.92 (2) 1.97 (2) 2.883 (2) 178 (2) iii ÁÁÁ N22—H22AÁÁÁCl2 0.91 (2) 2.43 (3) 3.3194 (18) 168 (2) chloride ions by N—H Cl hydrogen bonds, and to water N13—H13AÁÁÁCl1 0.91 (2) 2.48 (2) 3.335 (2) 156.9 (19) molecules by N—HÁÁÁO hydrogen bonds. Water molecules O3—H03BÁÁÁCl2iv 0.84 (4) 2.45 (4) 3.286 (2) 174 (3) and chloride ions are also linked together via O—HÁÁÁCl O2—H0BÁÁÁCl1 0.85 (3) 2.28 (3) 3.1171 (18) 172 (2) O2—H0AÁÁÁCl2 0.79 (3) 2.40 (3) 3.1833 (18) 175 (3) hydrogen bonds. In the crystal, all these intermolecular O3—H03AÁÁÁCl3 0.94 (4) 2.25 (4) 3.1586 (18) 164 (3) interactions result in a three-dimensional network. Symmetry codes: (i) x À 1; y; z; (ii) x; y À 1; z; (iii) Àx; Ày þ 1; Àz; (iv) Àx þ 1; Ày þ 1; Àz; (v) Àx þ 1; Ày þ 1; Àz þ 1; (vi) Àx; Ày þ 1; Àz þ 1. Related literature Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: For related structures, see: Guo et al. (2005); Fan et al. (2009); RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to Go´ker et al. (2005); Walther et al. (2006). solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999) and SHELXP97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97. The authors gratefully acknowledge financial support from the Education Department of Liaoning Province (2009 A 265) and Liaoning University. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2070). References Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Fan, P., Wang, L. & Zhang, H. (2009). Acta Cryst. E65, o2408. Experimental Go´ker, H., O´ zden, S., Yildiz, S. & Boykin, D. W. (2005). Eur. J. Med. Chem. 40, 1062–1069. Crystal data Guo, J., Wong, W.-K. & Wong, W.-Y. (2005). Polyhedron, 24, 927–939. + À ˚ Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. C6H8N3 ÁCl ÁH2O c = 16.862 (3) A Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Mr = 175.62 = 79.24 (3) Triclinic, P1 = 82.14 (3) Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. a = 7.2570 (15) A˚ = 78.34 (3) Walther, M., Wermann, H., Lutsche, M., Gu´nther, W., Go´rls, H. & Anders, E. b = 11.146 (2) A˚ V = 1305.3 (5) A˚ 3 (2006). J. Org. Chem. 71, 1399–1406. Acta Cryst. (2010). E66, o3169 doi:10.1107/S1600536810046106 Chen et al. o3169 supplementary materials supplementary materials Acta Cryst. (2010). E66, o3169 [ doi:10.1107/S1600536810046106 ] Pyridine-2-carboximidamidate chloride monohydrate Q. Chen, H. Zhang, F. Zhang and F. Liu Comment The pyridinecarboximidamidate derivatives have attracted a great attention due to their very potent antibacterial activities, interesting biological properties and applications in coordination chemistry, but a few samples have been reported (Guo et al., 2005; Góker et al., 2005; Walther et al., 2006; Fan et al., 2009). Here we report the structure of title compound + - C6H8N3 .Cl .H2O. The title compound is an organic salt and crystallizes with three formula units in the asymmetric unit (Fig. 1). The molecules are nonplanar with the C(NH2)2 groups twisted out of the ring planes. The bond lengths and angles exhibit normal values and are comparable with those in the related structures (Guo et al., 2005; Fan et al., 2009). In the crystal structure, pyridine carboximidamidate cations adopt three different connecting types (Fig. 2). Each pyridine carboximidamidate cation is linked to another cation through N—H···N hydrogen bonds, to chloride ions by N—H···Cl hydrogen bonds, and to water molecules by N—H···O hydrogen bonds. Water molecules and chloride ions are also linked together via O—H···Cl hydrogen bonds (Table 1). In the crystal structure, all these intermolecular interactions result in a three-dimensional network (Fig. 3). Experimental To a solution of sodium methoxide (5.15 mmol) in methanol (50 mL) was added 2-cyanopyridine (5.2 g, 4.99 mmol). The mixture was stirred at room temperature for 4 h. Then ammonium chloride (2.9 g, 5.42 mmol) was slowly added to the resulting solution and the mixture was stirred at room temperature for 68 h. The resulting suspension was filtered and the solvent was removed from the filtrate under reduced pressure. Purification by wash with ethyl ether gave 2-amidinopyridine hydrochloride (5.62 g, 92%) as an off-white solid. Colorless crystals were formed after several days. Refinement The H atoms were initially found in a difference Fourier map and their coordinates were refined freely. Figures Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids for non-H atoms. Fig. 2. View of the hydrogen bonding interactions in the title compound. sup-1 supplementary materials Fig. 3. Crystal packing of the title compound. Pyridine-2-carboximidamidate chloride monohydrate Crystal data + − C6H8N3 ·Cl ·H2O Z = 6 Mr = 175.62 F(000) = 552 −3 Triclinic, P1 Dx = 1.340 Mg m Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å a = 7.2570 (15) Å Cell parameters from 9445 reflections b = 11.146 (2) Å θ = 3.0–27.4° c = 16.862 (3) Å µ = 0.39 mm−1 α = 79.24 (3)° T = 293 K β = 82.14 (3)° Block, colourless γ = 78.34 (3)° 0.25 × 0.24 × 0.22 mm V = 1305.3 (5) Å3 Data collection Rigaku R-AXIS RAPID 5919 independent reflections diffractometer Radiation source: fine-focus sealed tube 4550 reflections with I > 2σ(I) graphite Rint = 0.024 -1 Detector resolution: 10 pixels mm θmax = 27.5°, θmin = 3.0° ω scans h = −9→9 Absorption correction: multi-scan k = −14→14 (ABSCOR; Higashi, 1995) Tmin = 0.909, Tmax = 0.918 l = −21→21 12872 measured reflections Refinement 2 Primary atom site location: structure-invariant direct Refinement on F methods Least-squares matrix: full Secondary atom site location: difference Fourier map 2 2 Hydrogen site location: inferred from neighbouring R[F > 2σ(F )] = 0.035 sites wR(F2) = 0.117 All H-atom parameters refined 2 2 2 w = 1/[σ (Fo ) + (0.0684P) ] S = 1.11 2 2 where P = (Fo + 2Fc )/3 5919 reflections (Δ/σ)max = 0.001 −3 418 parameters Δρmax = 0.23 e Å −3 0 restraints Δρmin = −0.26 e Å sup-2 supplementary materials Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance mat- rix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F2 against ALL reflections.