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ISSN: 2056-9890

Bis{3-[2-(methyl­sulfon­yl)pyrimidin-4-yl]pyridinium} tetra­chloridocadmium

aDepartment of City Science, Jiangsu City Vocation College, Nanjing 210003, People's Republic of China
*Correspondence e-mail: hudh@jstvu.edu.cn

(Received 1 October 2011; accepted 1 November 2011; online 23 November 2011)

In the title compound, (C10H10N3O2S)2[CdCl4], the CdII ion lies on a twofold axis and is coordinated by four chloride anions, with bond distances of 2.4787 (10) and 2.4410 (10) Å. A chain along the c axis is formed by C—H⋯N hydrogen-bonding inter­actions and a weak ππ inter­action is observed between the pyrimidine rings of two adjacent parallel chains [centroid–centroid distance = 3.722 (2) Å]. N—H⋯Cl, CN—H⋯Cl and N—H⋯O interactions also occur.

Related literature

For related structures, see: Huang et al. (2001[Huang, W., Gou, S., Hu, D., Chantrapromma, S., Fun, H. K. & Meng, Q. (2001). Inorg. Chem. 40, 1712-1715.]); Dong et al. (2008[Dong, H. Z., Zhu, H. B., Liu, X. & Gou, S. (2008). Polyhedron, 27, 2167-2174.], 2009[Dong, H. Z., Zhao, J., Gou, S. & Zhu, H. B. (2009). Polyhedron, 28, 1040-1048.]).

[Scheme 1]

Experimental

Crystal data
  • (C10H10N3O2S)2[CdCl4]

  • Mr = 726.8

  • Monoclinic, C 2/c

  • a = 17.556 (3) Å

  • b = 10.9541 (15) Å

  • c = 14.903 (2) Å

  • β = 113.354 (3)°

  • V = 2631.2 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.44 mm−1

  • T = 293 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.573, Tmax = 0.773

  • 6931 measured reflections

  • 2576 independent reflections

  • 1857 reflections with I > 2σ(I)

  • Rint = 0.049

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.070

  • S = 0.90

  • 2576 reflections

  • 173 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.77 e Å−3

  • Δρmin = −0.41 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯Cl1i 0.82 (3) 2.26 (3) 3.062 (4) 170 (3)
C2—H2⋯Cl1ii 0.93 2.79 3.603 (4) 146
C6—H6⋯Cl2i 0.93 2.72 3.577 (3) 153
C7—H7⋯N2iii 0.93 2.58 3.475 (5) 162
C10—H10A⋯Cl1iv 0.96 2.74 3.552 (6) 143
C10—H10C⋯O1v 0.96 2.53 3.433 (4) 156
Symmetry codes: (i) [x, -y+1, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iv) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (v) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Crystal engineering of coordination compounds has attracted a great deal of attention in the recent years because of their potential as functional materials (Huang et al., 2001; Dong et al., 2008, 2009). One of the most efficient and powerful strategies for constructing such compounds is directed self-assembly of designed organic ligands and inorganic metal ions. Although self-assembly directed by metal-containing species is mainly assisted by coordination bond-base approach, other non-covalent interactions such as hydrogen bonding and aromatic ππ stacking also have a significant impact on the architecture of the final product. One example is the dinuclear ZnII macrocyclic species reported by Huang et al. (2001). Here we describe the CdII title complex.

The title compound crystallizes in the monoclinic space group C2/c and every unit cell contains four CdII ions, eight 3-(2-methanesulfonyl-pyrimidin-4-yl)pyridinium cations (L) and sixteen chloride anions (Fig 1). Each Cd(II) ion is coordinated by four chloride anions, yielding a distorted tetrahedral coordination sphere with Cd—Cl1 and Cd—Cl2 distances in the range of 2.44–2.48Å and the corresponding Cl2—Cd—Cl1 bond angles are 112.64 (5)° (Cl2A—Cd1—Cl2), 111.85 (4)° (Cl2A—Cd1—Cl1), 102.49 (3)° (Cl2—Cd1—Cl1) and 102.49 (3)° (Cl2A—Cd1—Cl1A), respectively. A one-dimensional chain is formed by C7—H7···N2 hydrogen bonding interactions, as can be seen in Fig. 2; the corresponding bond length and bond angle are 3.474 (5)Å and 162°, respectively. A weak ππ interaction is observed between the pyrimidyl rings of two adjacent paralleled one-dimensional chains with the centroid-centroid separation of 3.722 (2) Å. A Cd2(HL)4Cl8 structural unit, as the result of C—H···Cl hydrogen bonding interaction, is formed and shown in Fig. 3, where the corresponding bond lengths and bond angles are 3.552 (6) Å, 143° (C10—H10A···Cl1); 3.603 (4) Å, 146° (C2—H2···Cl1); 3.577 (3) Å, 153° (C6—H6···Cl2) and 3.062 (4) Å, 170 (3)° (N3—H3A···Cl1), respectively.

Related literature top

For related structures, see: Huang et al. (2001); Dong et al. (2008, 2009).

Experimental top

All solvents and chemicals were of analytical grade and were purchased from Aldrich or ACROS. They were used without further purification. For the synthesis of the title compound, a solution of CdCl4 (6.4 mg, 0.025 mmol) in methanol (5 mL) was very slowly dropped on the top of a solution of L (11.76 mg, 0.05 mmol) in chloroform (5 mL) in a tube. Pale yellow single crystals formed after six days.

Refinement top

All hydrogen atoms were geometrically positioned (C—H 0.93–0.97 Å) and refined in riding motion, with Uiso(H)=1.2–1.5 Ueq of the parent atom. Proton H3a was refined freely.

Structure description top

Crystal engineering of coordination compounds has attracted a great deal of attention in the recent years because of their potential as functional materials (Huang et al., 2001; Dong et al., 2008, 2009). One of the most efficient and powerful strategies for constructing such compounds is directed self-assembly of designed organic ligands and inorganic metal ions. Although self-assembly directed by metal-containing species is mainly assisted by coordination bond-base approach, other non-covalent interactions such as hydrogen bonding and aromatic ππ stacking also have a significant impact on the architecture of the final product. One example is the dinuclear ZnII macrocyclic species reported by Huang et al. (2001). Here we describe the CdII title complex.

The title compound crystallizes in the monoclinic space group C2/c and every unit cell contains four CdII ions, eight 3-(2-methanesulfonyl-pyrimidin-4-yl)pyridinium cations (L) and sixteen chloride anions (Fig 1). Each Cd(II) ion is coordinated by four chloride anions, yielding a distorted tetrahedral coordination sphere with Cd—Cl1 and Cd—Cl2 distances in the range of 2.44–2.48Å and the corresponding Cl2—Cd—Cl1 bond angles are 112.64 (5)° (Cl2A—Cd1—Cl2), 111.85 (4)° (Cl2A—Cd1—Cl1), 102.49 (3)° (Cl2—Cd1—Cl1) and 102.49 (3)° (Cl2A—Cd1—Cl1A), respectively. A one-dimensional chain is formed by C7—H7···N2 hydrogen bonding interactions, as can be seen in Fig. 2; the corresponding bond length and bond angle are 3.474 (5)Å and 162°, respectively. A weak ππ interaction is observed between the pyrimidyl rings of two adjacent paralleled one-dimensional chains with the centroid-centroid separation of 3.722 (2) Å. A Cd2(HL)4Cl8 structural unit, as the result of C—H···Cl hydrogen bonding interaction, is formed and shown in Fig. 3, where the corresponding bond lengths and bond angles are 3.552 (6) Å, 143° (C10—H10A···Cl1); 3.603 (4) Å, 146° (C2—H2···Cl1); 3.577 (3) Å, 153° (C6—H6···Cl2) and 3.062 (4) Å, 170 (3)° (N3—H3A···Cl1), respectively.

For related structures, see: Huang et al. (2001); Dong et al. (2008, 2009).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering. Symmetry code for chlorine ions labelled A: -x,y,1/2-z.
[Figure 2] Fig. 2. : One-dimensional chain formed by C7—H7···N2 hydrogen bonding interactions.
[Figure 3] Fig. 3. : The Cd2(HL)4Cl8 structural unit, as the result of C—H···Cl hydrogen bonding interactions.
Bis{3-[2-(methylsulfonyl)pyrimidin-4-yl]pyridinium} tetrachloridocadmium top
Crystal data top
(C10H10N3O2S)2[CdCl4]F(000) = 1448
Mr = 726.8Dx = 1.835 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1574 reflections
a = 17.556 (3) Åθ = 2.3–23.3°
b = 10.9541 (15) ŵ = 1.44 mm1
c = 14.903 (2) ÅT = 293 K
β = 113.354 (3)°Block, yellow
V = 2631.2 (7) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2576 independent reflections
Radiation source: fine-focus sealed tube1857 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1521
Tmin = 0.573, Tmax = 0.773k = 1313
6931 measured reflectionsl = 1818
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.0212P)2]
where P = (Fo2 + 2Fc2)/3
2576 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.77 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
(C10H10N3O2S)2[CdCl4]V = 2631.2 (7) Å3
Mr = 726.8Z = 4
Monoclinic, C2/cMo Kα radiation
a = 17.556 (3) ŵ = 1.44 mm1
b = 10.9541 (15) ÅT = 293 K
c = 14.903 (2) Å0.40 × 0.30 × 0.20 mm
β = 113.354 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2576 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1857 reflections with I > 2σ(I)
Tmin = 0.573, Tmax = 0.773Rint = 0.049
6931 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.070H atoms treated by a mixture of independent and constrained refinement
S = 0.90Δρmax = 0.77 e Å3
2576 reflectionsΔρmin = 0.41 e Å3
173 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
Cd10.50000.12498 (4)0.75000.04176 (15)
C10.2419 (2)0.9045 (3)0.6362 (2)0.0302 (9)
C20.2441 (3)1.0195 (3)0.5153 (3)0.0489 (11)
H20.22451.08470.47230.059*
C30.3059 (2)0.9485 (3)0.5089 (3)0.0447 (10)
H30.32870.96550.46370.054*
C40.3329 (2)0.8511 (3)0.5717 (2)0.0283 (8)
C50.3996 (2)0.7683 (3)0.5742 (2)0.0290 (8)
C60.4485 (2)0.7960 (3)0.5240 (2)0.0366 (9)
H60.43880.86730.48720.044*
C70.5264 (2)0.6184 (4)0.5778 (3)0.0439 (10)
H70.57010.56940.57900.053*
C80.4791 (3)0.5852 (3)0.6274 (3)0.0458 (11)
H80.48960.51230.66220.055*
C90.4163 (2)0.6599 (3)0.6257 (3)0.0394 (10)
H90.38420.63740.65980.047*
C100.2557 (3)0.7643 (3)0.7978 (3)0.0530 (12)
H10A0.23650.74790.84860.080*
H10B0.31230.79150.82650.080*
H10C0.25230.69120.76090.080*
Cl10.59743 (7)0.24503 (10)0.88918 (7)0.0569 (3)
Cl20.42718 (7)0.00141 (9)0.82725 (7)0.0551 (3)
N10.29884 (18)0.8269 (2)0.63567 (19)0.0297 (7)
N20.21071 (19)0.9999 (3)0.5800 (2)0.0396 (8)
N30.5089 (2)0.7219 (3)0.5280 (2)0.0425 (9)
O10.20050 (18)0.9854 (2)0.77554 (18)0.0516 (8)
O20.11304 (17)0.8336 (3)0.66480 (19)0.0639 (9)
S10.19469 (6)0.87679 (9)0.72123 (6)0.0359 (2)
H3A0.535 (2)0.739 (3)0.495 (2)0.038 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0430 (3)0.0412 (3)0.0413 (3)0.0000.0170 (2)0.000
C10.033 (2)0.032 (2)0.028 (2)0.0004 (17)0.0141 (18)0.0027 (16)
C20.065 (3)0.044 (2)0.043 (2)0.020 (2)0.028 (2)0.0165 (19)
C30.052 (3)0.049 (2)0.046 (2)0.012 (2)0.035 (2)0.010 (2)
C40.031 (2)0.028 (2)0.0273 (19)0.0006 (17)0.0133 (17)0.0039 (15)
C50.028 (2)0.037 (2)0.0246 (19)0.0020 (18)0.0137 (17)0.0053 (16)
C60.038 (2)0.037 (2)0.036 (2)0.0058 (19)0.016 (2)0.0017 (17)
C70.040 (2)0.052 (3)0.042 (2)0.016 (2)0.019 (2)0.004 (2)
C80.052 (3)0.046 (2)0.042 (2)0.017 (2)0.022 (2)0.0069 (19)
C90.040 (2)0.046 (2)0.040 (2)0.008 (2)0.024 (2)0.0038 (18)
C100.066 (3)0.055 (3)0.056 (3)0.019 (2)0.043 (3)0.022 (2)
Cl10.0479 (7)0.0763 (8)0.0614 (7)0.0234 (6)0.0375 (6)0.0274 (6)
Cl20.0647 (8)0.0508 (6)0.0542 (7)0.0139 (6)0.0282 (6)0.0008 (5)
N10.0302 (18)0.0310 (16)0.0319 (17)0.0030 (14)0.0165 (15)0.0023 (13)
N20.044 (2)0.0389 (18)0.0403 (19)0.0099 (16)0.0218 (17)0.0016 (15)
N30.034 (2)0.062 (2)0.042 (2)0.0010 (19)0.0270 (19)0.0034 (18)
O10.072 (2)0.0427 (16)0.0565 (17)0.0024 (15)0.0432 (17)0.0102 (13)
O20.0387 (18)0.095 (2)0.0585 (19)0.0150 (17)0.0200 (16)0.0098 (16)
S10.0347 (6)0.0400 (5)0.0393 (6)0.0047 (5)0.0212 (5)0.0014 (5)
Geometric parameters (Å, º) top
Cd1—Cl2i2.4410 (10)C6—N31.319 (4)
Cd1—Cl22.4410 (10)C6—H60.9300
Cd1—Cl12.4787 (10)C7—N31.322 (5)
Cd1—Cl1i2.4787 (10)C7—C81.362 (5)
C1—N11.314 (4)C7—H70.9300
C1—N21.315 (4)C8—C91.366 (5)
C1—S11.794 (3)C8—H80.9300
C2—N21.329 (4)C9—H90.9300
C2—C31.368 (5)C10—S11.732 (3)
C2—H20.9300C10—H10A0.9600
C3—C41.374 (4)C10—H10B0.9600
C3—H30.9300C10—H10C0.9600
C4—N11.337 (4)N3—H3A0.81 (3)
C4—C51.470 (4)O1—S11.420 (2)
C5—C61.377 (4)O2—S11.425 (3)
C5—C91.380 (4)
Cl2i—Cd1—Cl2112.64 (5)N3—C7—H7120.7
Cl2i—Cd1—Cl1111.85 (4)C8—C7—H7120.7
Cl2—Cd1—Cl1102.49 (3)C7—C8—C9119.4 (4)
Cl2i—Cd1—Cl1i102.49 (3)C7—C8—H8120.3
Cl2—Cd1—Cl1i111.85 (4)C9—C8—H8120.3
Cl1—Cd1—Cl1i115.92 (6)C8—C9—C5121.2 (3)
N1—C1—N2129.4 (3)C8—C9—H9119.4
N1—C1—S1117.4 (2)C5—C9—H9119.4
N2—C1—S1113.1 (3)S1—C10—H10A109.5
N2—C2—C3123.3 (3)S1—C10—H10B109.5
N2—C2—H2118.4H10A—C10—H10B109.5
C3—C2—H2118.4S1—C10—H10C109.5
C2—C3—C4117.6 (3)H10A—C10—H10C109.5
C2—C3—H3121.2H10B—C10—H10C109.5
C4—C3—H3121.2C1—N1—C4115.6 (3)
N1—C4—C3120.5 (3)C1—N2—C2113.5 (3)
N1—C4—C5115.9 (3)C6—N3—C7123.9 (4)
C3—C4—C5123.6 (3)C6—N3—H3A118 (3)
C6—C5—C9116.8 (3)C7—N3—H3A118 (3)
C6—C5—C4120.8 (3)O1—S1—O2116.28 (17)
C9—C5—C4122.4 (3)O1—S1—C10109.55 (18)
N3—C6—C5120.2 (3)O2—S1—C10111.57 (19)
N3—C6—H6119.9O1—S1—C1108.19 (15)
C5—C6—H6119.9O2—S1—C1106.10 (16)
N3—C7—C8118.5 (4)C10—S1—C1104.33 (17)
Symmetry code: (i) x+1, y, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Cl1ii0.82 (3)2.26 (3)3.062 (4)170 (3)
C2—H2···Cl1iii0.932.793.603 (4)146
C6—H6···Cl2ii0.932.723.577 (3)153
C7—H7···N2iv0.932.583.475 (5)162
C10—H10A···Cl1v0.962.743.552 (6)143
C10—H10C···O1vi0.962.533.433 (4)156
Symmetry codes: (ii) x, y+1, z1/2; (iii) x1/2, y+3/2, z1/2; (iv) x+1/2, y1/2, z; (v) x1/2, y+1/2, z; (vi) x+1/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formula(C10H10N3O2S)2[CdCl4]
Mr726.8
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)17.556 (3), 10.9541 (15), 14.903 (2)
β (°) 113.354 (3)
V3)2631.2 (7)
Z4
Radiation typeMo Kα
µ (mm1)1.44
Crystal size (mm)0.40 × 0.30 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.573, 0.773
No. of measured, independent and
observed [I > 2σ(I)] reflections
6931, 2576, 1857
Rint0.049
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.070, 0.90
No. of reflections2576
No. of parameters173
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.77, 0.41

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···Cl1i0.82 (3)2.26 (3)3.062 (4)170 (3)
C2—H2···Cl1ii0.93002.79003.603 (4)146.00
C6—H6···Cl2i0.93002.72003.577 (3)153.00
C7—H7···N2iii0.93002.58003.475 (5)162.00
C10—H10A···Cl1iv0.96002.74003.552 (6)143.00
C10—H10C···O1v0.96002.53003.433 (4)156.00
Symmetry codes: (i) x, y+1, z1/2; (ii) x1/2, y+3/2, z1/2; (iii) x+1/2, y1/2, z; (iv) x1/2, y+1/2, z; (v) x+1/2, y1/2, z+3/2.
 

Acknowledgements

DH is indebted to the Natural Science Fund for Colleges and Universities in Jiangsu Province (09KJD150009) for financial support.

References

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