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1 metal-organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Oxo-1,2-dihydropyrimidin-3-ium di-l- chlorido-bis{dichloridobis[pyrimidin- 2(1H)-one-jN 3 ]cuprate(ii)} dihydrate Mukhtar A. Kurawa, Christopher J. Adams and A. Guy Orpen* School of Chemistry, University of Bristol, Bristol BS8 1TS, England Correspondence guy.orpen@bristol.ac.uk Experimental Crystal data (C 4 H 5 N 2 O) 2 [Cu 2 Cl 6 (C 4 H 4 N 2 O) 2 ]- 2H 2 O M r = Triclinic, P1 a = (4) Å b = (3) Å c = (4) Å = (3) Data collection Oxford Diffraction Gemini R Ultra diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) T min = 0.433, T max = 0.71 = (4) = (4) V = (5) Å 3 Z =1 Mo K radiation = 2.26 mm 1 T = 100 (2) K mm measured reflections 3902 independent reflections 3269 reflections with I > 2(I) R int = Received 9 June 2008; accepted 10 June 2008 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; R factor = 0.024; wr factor = 0.070; data-to-parameter ratio = The asymmetric unit of the title compound, (C 4 H 5 N 2 O) 2 - [Cu 2 Cl 6 (C 4 H 4 N 2 O) 2 ]2H 2 O, consists of one cation, one half of a centrosymmetric dianion and one water molecule. The centrosymmetric dianion formed by dimerization in the crystal structure has neutral pyrimidin-2-one ligands coordinated to each copper(ii) centre through Cu N bonds. The Cu atoms each have a distorted trigonal bipyramidal geometry, with the N atom of the pyrimidin-2-one ligand in an axial position, and dimerize by sharing two equatorial Cl atoms. N HCl, O HCl and N HO hydrogen bonds connect the anions, cations and water molecules, forming a three-dimensional network. Related literature The anion has an essentially similar coordination environment to that of the related compound [{(C 5 H 5 N)NH 2 }CuCl 3 ] 2 which has 3-aminopyridinium cations (Blanchette & Willett, 1988) as the nitrogen donors and is thus neutral, while the crystal structure of the cation was described by Furberg & Aas (1975) as its chloride salt. Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 180 parameters 2 restraints Table 1 Selected bond lengths (Å). Cu1 N (12) Cu1 Cl (4) Cu1 Cl (4) Symmetry code: (i) x; y þ 1; z þ 2. Table 2 Hydrogen-bond geometry (Å, ). H atoms treated by a mixture of independent and constrained refinement max = 0.49 e Å 3 min = 0.57 e Å 3 Cu1 Cl2 i (4) Cu1 Cl (4) D HA D H HA DA D HA N2 H2BCl1 ii (14) 171 N3 H3AO3 iii (18) 168 N4 H2ACl2 iv (14) 165 O3 H1Cl1 v (16) (17) (13) 166 (2) O3 H2Cl3 vi (17) (18) (13) 162 (2) Symmetry codes: (ii) x; y 1; z; (iii) x; y þ 1; z; (iv) x; y; z 1; (v) x þ 1; y þ 1; z þ 1; (vi) x þ 1; y; z. Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL). MAK thanks Bayero University, Kano, Nigeria, for funding. Oxford Diffraction Ltd are thanked for the loan of an Oxford Gemini R Ultra diffractometer to the University of Bristol. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SG2250). m924 Kurawa et al. doi: /s
2 metal-organic compounds References Blanchette, J. T. & Willett, R. D. (1988). Inorg. Chem. 27, Furberg, S. & Aas, J. B. (1975). Acta Chem. Scand. A29, Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Sheldrick, G. M. (2008). Acta Cryst. A64, Kurawa et al. (C 4 H 5 N 2 O) 2 [Cu 2 Cl 6 (C 4 H 4 N 2 O) 2 ]2H 2 O m925
3 supporting information [doi: /s ] 2-Oxo-1,2-dihydropyrimidin-3-ium di-µ-chlorido-bis- {dichloridobis[pyrimidin-2(1h)-one-κn 3 ]cuprate(ii)} dihydrate Mukhtar A. Kurawa, Christopher J. Adams and A. Guy Orpen S1. Comment N H Cl interactions have been extensively used in crystal engineering to design and synthesize materials with desired structures. We sought to further utilize these interactions by reacting 2-hydroxypyrimidine hydrochloride and copper(ii) chloride in a 2:1 ratio with the aim of synthesizing [C 4 H 5 N 2 O] 2 [CuCl 4 ]. However, the title compound I was obtained, which crystallizes in the triclinic system with the P1 space group. The copper coordination centres are similar to those described by Blanchette and Willett (1988) in [{(C 5 H 5 N)NH 2 }CuCl 3 ] 2. The H 2 O molecules and the [C 4 H 5 N 2 O] + cations (having both N atoms protonated and the O atoms atom deprotonated) are packed between the anions along the c-axis, the water forming O H Cl bridges between the anions while the cations form N H Cl and N H O bonds with the anions and water molecules respectively (Fig. 2). For related literature, see Blanchette & Willett (1988) and Furberg & Aas (1975). S2. Experimental Copper(II) chloride dihydrate and 2-hydroxypyrimidine hydrochloride in a 1:2 molar ratio were dissolved in concentrated hydrochloric acid solution. The solution was left to evaporate slowly at room temperature and resulted in the formation of green crystals after a few days. S3. Refinement H atoms bonded to O atoms were located in the difference map and refined with distance restraints of O H = 0.84 (2) Å with U iso (H) = 1.2U eq (O). Other H atoms were positioned geometrically and refined using a riding model, with C H = 0.93 Å and N H = 0.86 Å, with U iso (H) = 1.2 times U eq (C, N). sup-1
4 Figure 1 The molecular structure of I showing one dimeric dianion, one cation and a molecule of water of crystallization, with atom labels and 50% probability displacement ellipsoids for non-h atoms. sup-2
5 Figure 2 Packing of I in the ac plane, with O H Cl bridges between the water molecules and the dianions, N H O hydrogen bonds between cations and water molecules, and N H Cl hydrogen bonds between the anions and cations. 2-Oxo-1,2-dihydropyrimidin-3-ium di-µ-chlorido-bis{dichloridobis[pyrimidin-2(1h)-one-κn 3 ]cuprate(ii)} dihydrate Crystal data (C 4 H 5 N 2 O) 2 [Cu 2 Cl 6 (C 4 H 4 N 2 O) 2 ] 2H 2 O M r = Triclinic, P1 a = (4) Å b = (3) Å c = (4) Å α = (3) β = (4) γ = (4) V = (5) Å 3 Data collection Oxford Diffraction Gemini-R Ultra diffractometer Radiation source: fine-focus sealed tube Graphite monochromator ω (1 width) scans Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) T min = 0.433, T max = 0.71 Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections 180 parameters 2 restraints Z = 1 F(000) = 382 D x = Mg m 3 Mo Kα radiation, λ = Å Cell parameters from reflections θ = µ = 2.26 mm 1 T = 100 K Block, green mm measured reflections 3902 independent reflections 3269 reflections with I > 2σ(I) R int = θ max = 30.1, θ min = 2.4 h = k = l = Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H atoms treated by a mixture of independent and constrained refinement sup-3
6 w = 1/[σ 2 (F o2 ) + (0.0422P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max = Δρ max = 0.49 e Å 3 Δρ min = 0.57 e Å 3 Special details Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version (release CrysAlis171.NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 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 matrix. 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 F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 ) x y z U iso */U eq Cu (3) (2) (17) (6) Cl (5) (4) (3) (8) Cl (5) (4) (3) (8) Cl (6) (5) (4) (9) N (18) (15) (12) (2) N (19) (15) (13) (3) H2B * N (19) (16) (12) (3) H3A * N (19) (16) (13) (3) H2A * O (18) (15) (12) (3) O (17) (14) (11) (2) O (18) (15) (12) (3) C (2) (17) (15) (3) C (2) (18) (14) (3) H2C * C (2) (18) (15) (3) H3B * C (2) (18) (15) (3) H4A * C (2) (19) (15) (3) C (2) (19) (15) (3) H6A * C (2) (19) (15) (3) H7A * C (2) (19) (15) (3) H8A * H (3) (3) (19) (7)* H (3) (3) (2) (8)* sup-4
7 Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 Cu (11) (9) (10) (7) (7) (7) Cl (19) (16) (17) (13) (14) (12) Cl (17) (15) (16) (13) (13) (12) Cl (19) (18) (18) (14) (14) (14) N (6) (5) (6) (5) (5) (4) N (7) (5) (6) (5) (5) (5) N (6) (6) (6) (5) (5) (5) N (6) (6) (6) (5) (5) (5) O (7) (6) (6) (5) (5) (5) O (6) (5) (5) (5) (5) (4) O (7) (6) (6) (5) (5) (5) C (7) (6) (7) (5) (6) (5) C (7) (7) (7) (6) (6) (5) C (8) (7) (7) (6) (6) (5) C (8) (7) (7) (6) (6) (6) C (8) (7) (7) (6) (6) (6) C (8) (7) (7) (6) (6) (5) C (8) (7) (7) (6) (6) (5) C (8) (7) (7) (6) (6) (6) Geometric parameters (Å, º) Cu1 N (12) N4 H2A Cu1 Cl (4) O1 C (19) Cu1 Cl (4) O2 C (2) Cu1 Cl2 i (4) O3 H (16) Cu1 Cl (4) O3 H (17) Cl2 Cu1 i (4) C2 C (2) N1 C (2) C2 H2C N1 C (19) C3 C (2) N2 C (2) C3 H3B N2 C (19) C4 H4A N2 H2B C6 C (2) N3 C (2) C6 H6A N3 C (2) C7 C (2) N3 H3A C7 H7A N4 C (2) C8 H8A N4 C (2) N1 Cu1 Cl (4) O2 C1 N (14) N1 Cu1 Cl (4) O2 C1 N (14) Cl3 Cu1 Cl (15) N1 C1 N (13) N1 Cu1 Cl2 i (4) N1 C2 C (14) Cl3 Cu1 Cl2 i (16) N1 C2 H2C Cl1 Cu1 Cl2 i (15) C3 C2 H2C sup-5
8 N1 Cu1 Cl (4) C4 C3 C (15) Cl3 Cu1 Cl (15) C4 C3 H3B Cl1 Cu1 Cl (14) C2 C3 H3B Cl2 i Cu1 Cl (14) N2 C4 C (14) Cu1 i Cl2 Cu (14) N2 C4 H4A C2 N1 C (13) C3 C4 H4A C2 N1 Cu (10) O1 C5 N (15) C1 N1 Cu (10) O1 C5 N (15) C4 N2 C (13) N4 C5 N (13) C4 N2 H2B N3 C6 C (15) C1 N2 H2B N3 C6 H6A C6 N3 C (14) C7 C6 H6A C6 N3 H3A C6 C7 C (15) C5 N3 H3A C6 C7 H7A C8 N4 C (14) C8 C7 H7A C8 N4 H2A N4 C8 C (15) C5 N4 H2A N4 C8 H8A H1 O3 H2 109 (2) C7 C8 H8A N1 Cu1 Cl2 Cu1 i (4) C4 N2 C1 N1 6.1 (2) Cl3 Cu1 Cl2 Cu1 i (16) C1 N1 C2 C3 2.4 (2) Cl1 Cu1 Cl2 Cu1 i (15) Cu1 N1 C2 C (11) Cl2 i Cu1 Cl2 Cu1 i 0.0 N1 C2 C3 C4 2.5 (2) Cl3 Cu1 N1 C (13) C1 N2 C4 C3 1.5 (2) Cl2 i Cu1 N1 C (13) C2 C3 C4 N2 2.9 (2) Cl2 Cu1 N1 C (13) C8 N4 C5 O (16) Cl3 Cu1 N1 C (10) C8 N4 C5 N3 2.3 (2) Cl2 i Cu1 N1 C (10) C6 N3 C5 O (16) Cl2 Cu1 N1 C (10) C6 N3 C5 N4 3.2 (2) C2 N1 C1 O (15) C5 N3 C6 C7 2.4 (2) Cu1 N1 C1 O2 4.8 (2) N3 C6 C7 C8 0.4 (2) C2 N1 C1 N2 6.4 (2) C5 N4 C8 C7 0.7 (2) Cu1 N1 C1 N (10) C6 C7 C8 N4 0.4 (2) C4 N2 C1 O (15) Symmetry code: (i) x, y+1, z+2. Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A N2 H2B Cl1 ii (14) 171 N3 H3A O3 iii (18) 168 N4 H2A Cl2 iv (14) 165 O3 H1 Cl1 v 0.82 (2) 2.43 (2) (13) 166 (2) O3 H2 Cl3 vi 0.84 (2) 2.45 (2) (13) 162 (2) Symmetry codes: (ii) x, y 1, z; (iii) x, y+1, z; (iv) x, y, z 1; (v) x+1, y+1, z+1; (vi) x+1, y, z. sup-6
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