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catena-Poly[[[4,6-bis­­(2-pyrid­yl)-1,3,5-triazin-2-olato]copper(II)]-μ-chlorido]

aDepartment of Chemistry, Guangdong University of Education, Guangzhou 510303, People's Republic of China
*Correspondence e-mail: caoml@mail3.sysu.edu.cn

(Received 12 March 2011; accepted 5 May 2011; online 11 May 2011)

The title compound, [Cu(C13H8N5O)Cl]n, has a chain structure parallel to [100] with Cu2+ cations in a trigonal–bipyramidal coordination environment. The ligand adopts a tridentate tripyridyl coordination mode and a chloride ion acts as a bridge. The chains are linked via weak C—H⋯O and C—H⋯Cl hydrogen bonds into a three-dimensional supra­molecular network.

Related literature

For background to rigid multidentate polypyridyl ligands containing a triazine ring as a bridge, see: Zhou, Li, Zheng et al. (2006[Zhou, X.-P., Li, D., Zheng, S.-L., Zhang, X. & Wu, T. (2006). Inorg. Chem. 45, 7119-7125.]); Zhou, Li, Wu et al. (2006[Zhou, X.-P., Li, D., Wu, T. & Zhang, X. (2006). Discuss. Faraday Soc. p. 2435.]). For the synthesis of the ligand, see: Wieprecht et al. (2005[Wieprecht, T., Dubs, M.-J. & Schlingloff, G. (2005). Int. Patent WO 2005105303.]). For complexes based on the ligand, see: Cao et al. (2008[Cao, M.-L., Hao, H.-G., Zhang, W.-X. & Ye, B.-H. (2008). Inorg. Chem. 47, 8126-8133], 2009[Cao, M.-L., Wu, J.-J., Mo, H.-J. & Ye, B.-H. (2009). J. Am. Chem. Soc. 131, 3458-3459]).

[Scheme 1]

Experimental

Crystal data
  • [Cu(C13H8N5O)Cl]

  • Mr = 349.23

  • Monoclinic, P 21 /m

  • a = 3.7687 (13) Å

  • b = 13.698 (5) Å

  • c = 11.852 (4) Å

  • β = 92.851 (6)°

  • V = 611.1 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.01 mm−1

  • T = 293 K

  • 0.09 × 0.09 × 0.07 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.840, Tmax = 0.872

  • 3063 measured reflections

  • 1109 independent reflections

  • 952 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.085

  • S = 1.03

  • 1109 reflections

  • 103 parameters

  • H-atom parameters constrained

  • Δρmax = 0.49 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3A⋯O1i 0.96 2.37 3.145 (2) 138
C2—H2A⋯Cl1ii 0.96 2.89 3.836 (3) 170
Symmetry codes: (i) [-x+2, y+{\script{3\over 2}}, -z]; (ii) [-x, y+{\script{3\over 2}}, -z+1].

Data collection: SMART (Bruker, 2005[Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The rigid multidentate polypyridyl ligands containing a triazine ring as a bridge have attracted greatly our attention due to their coordination diversity (Zhou, Li, Zheng et al., 2006; Zhou, Li, Wu et al. 2006). Although coordination chemistry of the symmetrical ligands like TPT has been well explored, the observations on the asymmetric ligands containing triazine ring are still rare. As a contribution to the synthesis and structural studies of coordination abilities of 4,6-bis(2-pyridyl)-1,3,5-triazin-2-ol ligand (Wieprecht et al., 2005; Cao et al., 2008, 2009), I present here the crystal structure of the title compound (Fig. 1)- a new copper(II) complex with the ligand. Within the title compound, the copper(II) center is five-coordinated respectively by three N atoms [the distances of Cu—N are in the range of 1.896 (2) - 2.049 (2) Å] from the ligand and two Cl atoms [the bond lengths of Cu—Cl are 2.224 (1) Å and 2.778 (2) Å]. The complex is a chain structure, in which the ligand adopts a tridentate tripyridyl coordination mode and the chloride ion acts as a bridge (Fig. 2). The chains are linked via weak hydrogen bondings of C—H···O and C—H···Cl into a three-dimensional supramolecular network.

Related literature top

For background to rigid multidentate polypyridyl ligands containing a triazine ring as a bridge, see: Zhou, Li, Zheng et al. (2006); Zhou, Li, Wu et al. (2006). For the synthesis of the ligand, see: Wieprecht et al. (2005). For complexes based on the ligand, see: Cao et al. (2008, and 2009).

Experimental top

The ligand 4,6-bis(2-pyridyl)-1,3,5-triazin-2-ol was prepared according to previously reported procedures (Wieprecht et al., 2005), yield 56%. The ligand (0.125 g, 0.5 mmol), CuCl2(0.07 g, 0.5 mmol), 7 ml distilled water and 7 ml ethanol were put into a 25 ml Teflon-lined Parr. The mixture was heated to 100 °C for 48 h, and then cooled to room temperature at a rate of 5 °C/h. The obtained mixture was filtered and green crystals were obtained. Yield: 0.108 g, 62% (base on the ligand). Anal. Calcd. for C13H8ClCuN5O (%): C 44.71, H 2.31, N 20.05; Found(%): C 44.52, H 2.43, N 19.91

Refinement top

All H atoms were calculated geometrically and treated as riding with C—H = 0.96 Å and Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i): x, 0.5 - y, z; (ii): 1 + x, y, z].
[Figure 2] Fig. 2. The chain structure in the title compound, H atoms are omitted for clarity. [Symmetry codes: (i): x, 0.5 - y, z; (ii): 1 + x, y, z; (iii): 1 + x, 0.5 - y, z; (iv): 2 + x, y, z; (v): 2 + x, 0.5 - y, z; (vi): 3 + x, y, z].
catena-Poly[[4,6-bis(2-pyridyl)-1,3,5-triazin-2-olato]copper(II)]- µ-chlorido] top
Crystal data top
[Cu(C13H8N5O)Cl]F(000) = 350
Mr = 349.23Dx = 1.898 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 1109 reflections
a = 3.7687 (13) Åθ = 2.3–25.0°
b = 13.698 (5) ŵ = 2.01 mm1
c = 11.852 (4) ÅT = 293 K
β = 92.851 (6)°Block, green
V = 611.1 (4) Å30.09 × 0.09 × 0.07 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1109 independent reflections
Radiation source: fine-focus sealed tube952 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ϕ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 44
Tmin = 0.840, Tmax = 0.872k = 1616
3063 measured reflectionsl = 1413
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0528P)2]
where P = (Fo2 + 2Fc2)/3
1109 reflections(Δ/σ)max < 0.001
103 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
[Cu(C13H8N5O)Cl]V = 611.1 (4) Å3
Mr = 349.23Z = 2
Monoclinic, P21/mMo Kα radiation
a = 3.7687 (13) ŵ = 2.01 mm1
b = 13.698 (5) ÅT = 293 K
c = 11.852 (4) Å0.09 × 0.09 × 0.07 mm
β = 92.851 (6)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1109 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
952 reflections with I > 2σ(I)
Tmin = 0.840, Tmax = 0.872Rint = 0.030
3063 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.03Δρmax = 0.49 e Å3
1109 reflectionsΔρmin = 0.27 e Å3
103 parameters
Special details top

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 F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 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 (Å2) top
xyzUiso*/Ueq
Cu10.39787 (13)0.25000.32504 (4)0.0267 (2)
Cl10.0169 (3)0.25000.46244 (8)0.0325 (3)
O11.0547 (10)0.25000.1071 (3)0.0457 (9)
N10.4310 (6)0.39688 (17)0.29470 (19)0.0252 (5)
N20.6066 (9)0.25000.1827 (3)0.0288 (8)
N30.8356 (7)0.33967 (17)0.03443 (19)0.0295 (6)
C10.3326 (8)0.4686 (2)0.3618 (3)0.0294 (7)
H1A0.22820.45230.43160.035*
C20.3786 (8)0.5661 (2)0.3345 (2)0.0353 (8)
H2A0.30900.61680.38490.042*
C30.5252 (9)0.5888 (2)0.2342 (3)0.0357 (8)
H3A0.55380.65590.21300.043*
C40.6294 (8)0.5153 (2)0.1635 (2)0.0304 (7)
H4A0.73500.52980.09340.036*
C50.5795 (7)0.4205 (2)0.1963 (2)0.0249 (7)
C60.6831 (8)0.3335 (2)0.1299 (2)0.0249 (6)
C70.9152 (11)0.25000.0159 (3)0.0308 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0324 (3)0.0226 (3)0.0256 (3)0.0000.0083 (2)0.000
Cl10.0327 (6)0.0348 (6)0.0312 (6)0.0000.0117 (4)0.000
O10.063 (2)0.0376 (19)0.0392 (19)0.0000.0247 (16)0.000
N10.0264 (14)0.0236 (13)0.0257 (12)0.0008 (10)0.0025 (10)0.0006 (10)
N20.042 (2)0.0183 (18)0.0272 (19)0.0000.0114 (16)0.000
N30.0319 (15)0.0318 (15)0.0254 (13)0.0008 (11)0.0069 (11)0.0019 (10)
C10.0306 (17)0.0287 (17)0.0290 (15)0.0014 (13)0.0031 (12)0.0039 (12)
C20.0368 (19)0.0290 (17)0.0400 (19)0.0052 (14)0.0000 (15)0.0083 (14)
C30.039 (2)0.0246 (17)0.0434 (19)0.0013 (13)0.0019 (15)0.0045 (13)
C40.0325 (18)0.0238 (16)0.0347 (17)0.0035 (13)0.0011 (14)0.0032 (12)
C50.0224 (16)0.0266 (16)0.0255 (15)0.0002 (12)0.0012 (12)0.0005 (11)
C60.0222 (15)0.0254 (16)0.0268 (15)0.0009 (12)0.0020 (12)0.0016 (12)
C70.030 (2)0.038 (3)0.024 (2)0.0000.0038 (18)0.000
Geometric parameters (Å, º) top
Cu1—N21.896 (3)N3—C71.405 (3)
Cu1—N1i2.049 (2)C1—C21.387 (4)
Cu1—N12.049 (2)C1—H1A0.9602
Cu1—Cl12.2239 (12)C2—C31.371 (4)
Cu1—Cl1ii2.778 (2)C2—H2A0.9602
O1—C71.225 (5)C3—C41.380 (4)
N1—C11.329 (4)C3—H3A0.9603
N1—C51.358 (4)C4—C51.371 (4)
N2—C6i1.343 (3)C4—H4A0.9602
N2—C61.343 (3)C5—C61.491 (4)
N3—C61.297 (4)C7—N3i1.405 (3)
N2—Cu1—N1i79.18 (7)C3—C2—C1118.8 (3)
N2—Cu1—N179.18 (7)C3—C2—H2A120.6
N1i—Cu1—N1158.25 (13)C1—C2—H2A120.6
N2—Cu1—Cl1164.32 (11)C2—C3—C4120.0 (3)
N1i—Cu1—Cl1100.12 (7)C2—C3—H3A120.0
N1—Cu1—Cl1100.12 (7)C4—C3—H3A120.0
Cl1ii—Cu1—Cl1100.12 (7)C5—C4—C3118.2 (3)
Cl1ii—Cu1—N1100.12 (7)C5—C4—H4A120.6
Cl1ii—Cu1—N2100.12 (7)C3—C4—H4A121.2
C1—N1—C5118.5 (3)N1—C5—C4122.5 (3)
C1—N1—Cu1126.9 (2)N1—C5—C6113.1 (2)
C5—N1—Cu1114.60 (19)C4—C5—C6124.3 (3)
C6i—N2—C6116.9 (3)N3—C6—N2125.2 (3)
C6i—N2—Cu1121.53 (17)N3—C6—C5123.2 (2)
C6—N2—Cu1121.53 (17)N2—C6—C5111.5 (3)
C6—N3—C7115.3 (2)O1—C7—N3119.01 (17)
N1—C1—C2122.1 (3)O1—C7—N3i119.01 (17)
N1—C1—H1A118.8N3—C7—N3i122.0 (3)
C2—C1—H1A119.1
Symmetry codes: (i) x, y+1/2, z; (ii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O1iii0.962.373.145 (2)138
C2—H2A···Cl1iv0.962.893.836 (3)170
Symmetry codes: (iii) x+2, y+3/2, z; (iv) x, y+3/2, z+1.

Experimental details

Crystal data
Chemical formula[Cu(C13H8N5O)Cl]
Mr349.23
Crystal system, space groupMonoclinic, P21/m
Temperature (K)293
a, b, c (Å)3.7687 (13), 13.698 (5), 11.852 (4)
β (°) 92.851 (6)
V3)611.1 (4)
Z2
Radiation typeMo Kα
µ (mm1)2.01
Crystal size (mm)0.09 × 0.09 × 0.07
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.840, 0.872
No. of measured, independent and
observed [I > 2σ(I)] reflections
3063, 1109, 952
Rint0.030
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.085, 1.03
No. of reflections1109
No. of parameters103
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.49, 0.27

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3A···O1i0.962.3663.145 (2)138
C2—H2A···Cl1ii0.962.893.836 (3)170
Symmetry codes: (i) x+2, y+3/2, z; (ii) x, y+3/2, z+1.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 21001031) and the Special Research Fund for PhD of Guangdong University of Education (grant No. 10ARF05).

References

First citationBruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCao, M.-L., Hao, H.-G., Zhang, W.-X. & Ye, B.-H. (2008). Inorg. Chem. 47, 8126–8133  Web of Science CrossRef PubMed CAS Google Scholar
First citationCao, M.-L., Wu, J.-J., Mo, H.-J. & Ye, B.-H. (2009). J. Am. Chem. Soc. 131, 3458–3459  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWieprecht, T., Dubs, M.-J. & Schlingloff, G. (2005). Int. Patent WO 2005105303.  Google Scholar
First citationZhou, X.-P., Li, D., Wu, T. & Zhang, X. (2006). Discuss. Faraday Soc. p. 2435.  Google Scholar
First citationZhou, X.-P., Li, D., Zheng, S.-L., Zhang, X. & Wu, T. (2006). Inorg. Chem. 45, 7119–7125.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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