metal-organic compounds
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
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 π–π 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.
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536811045995/vn2019sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045995/vn2019Isup2.hkl
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.
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.
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 π–π 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 π–π 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.
C2/c and every 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 weakFor related structures, see: Huang et al. (2001); Dong et al. (2008, 2009).
Data collection: SMART (Bruker, 2007); cell
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).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. | |
Fig. 2. : One-dimensional chain formed by C7—H7···N2 hydrogen bonding interactions. | |
Fig. 3. : The Cd2(HL)4Cl8 structural unit, as the result of C—H···Cl hydrogen bonding interactions. |
(C10H10N3O2S)2[CdCl4] | F(000) = 1448 |
Mr = 726.8 | Dx = 1.835 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1574 reflections |
a = 17.556 (3) Å | θ = 2.3–23.3° |
b = 10.9541 (15) Å | µ = 1.44 mm−1 |
c = 14.903 (2) Å | T = 293 K |
β = 113.354 (3)° | Block, yellow |
V = 2631.2 (7) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2576 independent reflections |
Radiation source: fine-focus sealed tube | 1857 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
φ and ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −15→21 |
Tmin = 0.573, Tmax = 0.773 | k = −13→13 |
6931 measured reflections | l = −18→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.070 | H 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 parameters | Δρmax = 0.77 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
(C10H10N3O2S)2[CdCl4] | V = 2631.2 (7) Å3 |
Mr = 726.8 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 17.556 (3) Å | µ = 1.44 mm−1 |
b = 10.9541 (15) Å | T = 293 K |
c = 14.903 (2) Å | 0.40 × 0.30 × 0.20 mm |
β = 113.354 (3)° |
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 = 0.773 | Rint = 0.049 |
6931 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.070 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | Δρmax = 0.77 e Å−3 |
2576 reflections | Δρmin = −0.41 e Å−3 |
173 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.5000 | 0.12498 (4) | 0.7500 | 0.04176 (15) | |
C1 | 0.2419 (2) | 0.9045 (3) | 0.6362 (2) | 0.0302 (9) | |
C2 | 0.2441 (3) | 1.0195 (3) | 0.5153 (3) | 0.0489 (11) | |
H2 | 0.2245 | 1.0847 | 0.4723 | 0.059* | |
C3 | 0.3059 (2) | 0.9485 (3) | 0.5089 (3) | 0.0447 (10) | |
H3 | 0.3287 | 0.9655 | 0.4637 | 0.054* | |
C4 | 0.3329 (2) | 0.8511 (3) | 0.5717 (2) | 0.0283 (8) | |
C5 | 0.3996 (2) | 0.7683 (3) | 0.5742 (2) | 0.0290 (8) | |
C6 | 0.4485 (2) | 0.7960 (3) | 0.5240 (2) | 0.0366 (9) | |
H6 | 0.4388 | 0.8673 | 0.4872 | 0.044* | |
C7 | 0.5264 (2) | 0.6184 (4) | 0.5778 (3) | 0.0439 (10) | |
H7 | 0.5701 | 0.5694 | 0.5790 | 0.053* | |
C8 | 0.4791 (3) | 0.5852 (3) | 0.6274 (3) | 0.0458 (11) | |
H8 | 0.4896 | 0.5123 | 0.6622 | 0.055* | |
C9 | 0.4163 (2) | 0.6599 (3) | 0.6257 (3) | 0.0394 (10) | |
H9 | 0.3842 | 0.6374 | 0.6598 | 0.047* | |
C10 | 0.2557 (3) | 0.7643 (3) | 0.7978 (3) | 0.0530 (12) | |
H10A | 0.2365 | 0.7479 | 0.8486 | 0.080* | |
H10B | 0.3123 | 0.7915 | 0.8265 | 0.080* | |
H10C | 0.2523 | 0.6912 | 0.7609 | 0.080* | |
Cl1 | 0.59743 (7) | 0.24503 (10) | 0.88918 (7) | 0.0569 (3) | |
Cl2 | 0.42718 (7) | 0.00141 (9) | 0.82725 (7) | 0.0551 (3) | |
N1 | 0.29884 (18) | 0.8269 (2) | 0.63567 (19) | 0.0297 (7) | |
N2 | 0.21071 (19) | 0.9999 (3) | 0.5800 (2) | 0.0396 (8) | |
N3 | 0.5089 (2) | 0.7219 (3) | 0.5280 (2) | 0.0425 (9) | |
O1 | 0.20050 (18) | 0.9854 (2) | 0.77554 (18) | 0.0516 (8) | |
O2 | 0.11304 (17) | 0.8336 (3) | 0.66480 (19) | 0.0639 (9) | |
S1 | 0.19469 (6) | 0.87679 (9) | 0.72123 (6) | 0.0359 (2) | |
H3A | 0.535 (2) | 0.739 (3) | 0.495 (2) | 0.038 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0430 (3) | 0.0412 (3) | 0.0413 (3) | 0.000 | 0.0170 (2) | 0.000 |
C1 | 0.033 (2) | 0.032 (2) | 0.028 (2) | 0.0004 (17) | 0.0141 (18) | −0.0027 (16) |
C2 | 0.065 (3) | 0.044 (2) | 0.043 (2) | 0.020 (2) | 0.028 (2) | 0.0165 (19) |
C3 | 0.052 (3) | 0.049 (2) | 0.046 (2) | 0.012 (2) | 0.035 (2) | 0.010 (2) |
C4 | 0.031 (2) | 0.028 (2) | 0.0273 (19) | −0.0006 (17) | 0.0133 (17) | −0.0039 (15) |
C5 | 0.028 (2) | 0.037 (2) | 0.0246 (19) | −0.0020 (18) | 0.0137 (17) | −0.0053 (16) |
C6 | 0.038 (2) | 0.037 (2) | 0.036 (2) | 0.0058 (19) | 0.016 (2) | 0.0017 (17) |
C7 | 0.040 (2) | 0.052 (3) | 0.042 (2) | 0.016 (2) | 0.019 (2) | −0.004 (2) |
C8 | 0.052 (3) | 0.046 (2) | 0.042 (2) | 0.017 (2) | 0.022 (2) | 0.0069 (19) |
C9 | 0.040 (2) | 0.046 (2) | 0.040 (2) | 0.008 (2) | 0.024 (2) | 0.0038 (18) |
C10 | 0.066 (3) | 0.055 (3) | 0.056 (3) | 0.019 (2) | 0.043 (3) | 0.022 (2) |
Cl1 | 0.0479 (7) | 0.0763 (8) | 0.0614 (7) | −0.0234 (6) | 0.0375 (6) | −0.0274 (6) |
Cl2 | 0.0647 (8) | 0.0508 (6) | 0.0542 (7) | −0.0139 (6) | 0.0282 (6) | −0.0008 (5) |
N1 | 0.0302 (18) | 0.0310 (16) | 0.0319 (17) | 0.0030 (14) | 0.0165 (15) | −0.0023 (13) |
N2 | 0.044 (2) | 0.0389 (18) | 0.0403 (19) | 0.0099 (16) | 0.0218 (17) | 0.0016 (15) |
N3 | 0.034 (2) | 0.062 (2) | 0.042 (2) | 0.0010 (19) | 0.0270 (19) | −0.0034 (18) |
O1 | 0.072 (2) | 0.0427 (16) | 0.0565 (17) | 0.0024 (15) | 0.0432 (17) | −0.0102 (13) |
O2 | 0.0387 (18) | 0.095 (2) | 0.0585 (19) | −0.0150 (17) | 0.0200 (16) | −0.0098 (16) |
S1 | 0.0347 (6) | 0.0400 (5) | 0.0393 (6) | 0.0047 (5) | 0.0212 (5) | −0.0014 (5) |
Cd1—Cl2i | 2.4410 (10) | C6—N3 | 1.319 (4) |
Cd1—Cl2 | 2.4410 (10) | C6—H6 | 0.9300 |
Cd1—Cl1 | 2.4787 (10) | C7—N3 | 1.322 (5) |
Cd1—Cl1i | 2.4787 (10) | C7—C8 | 1.362 (5) |
C1—N1 | 1.314 (4) | C7—H7 | 0.9300 |
C1—N2 | 1.315 (4) | C8—C9 | 1.366 (5) |
C1—S1 | 1.794 (3) | C8—H8 | 0.9300 |
C2—N2 | 1.329 (4) | C9—H9 | 0.9300 |
C2—C3 | 1.368 (5) | C10—S1 | 1.732 (3) |
C2—H2 | 0.9300 | C10—H10A | 0.9600 |
C3—C4 | 1.374 (4) | C10—H10B | 0.9600 |
C3—H3 | 0.9300 | C10—H10C | 0.9600 |
C4—N1 | 1.337 (4) | N3—H3A | 0.81 (3) |
C4—C5 | 1.470 (4) | O1—S1 | 1.420 (2) |
C5—C6 | 1.377 (4) | O2—S1 | 1.425 (3) |
C5—C9 | 1.380 (4) | ||
Cl2i—Cd1—Cl2 | 112.64 (5) | N3—C7—H7 | 120.7 |
Cl2i—Cd1—Cl1 | 111.85 (4) | C8—C7—H7 | 120.7 |
Cl2—Cd1—Cl1 | 102.49 (3) | C7—C8—C9 | 119.4 (4) |
Cl2i—Cd1—Cl1i | 102.49 (3) | C7—C8—H8 | 120.3 |
Cl2—Cd1—Cl1i | 111.85 (4) | C9—C8—H8 | 120.3 |
Cl1—Cd1—Cl1i | 115.92 (6) | C8—C9—C5 | 121.2 (3) |
N1—C1—N2 | 129.4 (3) | C8—C9—H9 | 119.4 |
N1—C1—S1 | 117.4 (2) | C5—C9—H9 | 119.4 |
N2—C1—S1 | 113.1 (3) | S1—C10—H10A | 109.5 |
N2—C2—C3 | 123.3 (3) | S1—C10—H10B | 109.5 |
N2—C2—H2 | 118.4 | H10A—C10—H10B | 109.5 |
C3—C2—H2 | 118.4 | S1—C10—H10C | 109.5 |
C2—C3—C4 | 117.6 (3) | H10A—C10—H10C | 109.5 |
C2—C3—H3 | 121.2 | H10B—C10—H10C | 109.5 |
C4—C3—H3 | 121.2 | C1—N1—C4 | 115.6 (3) |
N1—C4—C3 | 120.5 (3) | C1—N2—C2 | 113.5 (3) |
N1—C4—C5 | 115.9 (3) | C6—N3—C7 | 123.9 (4) |
C3—C4—C5 | 123.6 (3) | C6—N3—H3A | 118 (3) |
C6—C5—C9 | 116.8 (3) | C7—N3—H3A | 118 (3) |
C6—C5—C4 | 120.8 (3) | O1—S1—O2 | 116.28 (17) |
C9—C5—C4 | 122.4 (3) | O1—S1—C10 | 109.55 (18) |
N3—C6—C5 | 120.2 (3) | O2—S1—C10 | 111.57 (19) |
N3—C6—H6 | 119.9 | O1—S1—C1 | 108.19 (15) |
C5—C6—H6 | 119.9 | O2—S1—C1 | 106.10 (16) |
N3—C7—C8 | 118.5 (4) | C10—S1—C1 | 104.33 (17) |
Symmetry code: (i) −x+1, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···Cl1ii | 0.82 (3) | 2.26 (3) | 3.062 (4) | 170 (3) |
C2—H2···Cl1iii | 0.93 | 2.79 | 3.603 (4) | 146 |
C6—H6···Cl2ii | 0.93 | 2.72 | 3.577 (3) | 153 |
C7—H7···N2iv | 0.93 | 2.58 | 3.475 (5) | 162 |
C10—H10A···Cl1v | 0.96 | 2.74 | 3.552 (6) | 143 |
C10—H10C···O1vi | 0.96 | 2.53 | 3.433 (4) | 156 |
Symmetry codes: (ii) x, −y+1, z−1/2; (iii) x−1/2, −y+3/2, z−1/2; (iv) x+1/2, y−1/2, z; (v) x−1/2, y+1/2, z; (vi) −x+1/2, y−1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | (C10H10N3O2S)2[CdCl4] |
Mr | 726.8 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.556 (3), 10.9541 (15), 14.903 (2) |
β (°) | 113.354 (3) |
V (Å3) | 2631.2 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.44 |
Crystal size (mm) | 0.40 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.573, 0.773 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6931, 2576, 1857 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.070, 0.90 |
No. of reflections | 2576 |
No. of parameters | 173 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.77, −0.41 |
Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···Cl1i | 0.82 (3) | 2.26 (3) | 3.062 (4) | 170 (3) |
C2—H2···Cl1ii | 0.9300 | 2.7900 | 3.603 (4) | 146.00 |
C6—H6···Cl2i | 0.9300 | 2.7200 | 3.577 (3) | 153.00 |
C7—H7···N2iii | 0.9300 | 2.5800 | 3.475 (5) | 162.00 |
C10—H10A···Cl1iv | 0.9600 | 2.7400 | 3.552 (6) | 143.00 |
C10—H10C···O1v | 0.9600 | 2.5300 | 3.433 (4) | 156.00 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) x+1/2, y−1/2, z; (iv) x−1/2, y+1/2, z; (v) −x+1/2, y−1/2, −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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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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 π–π 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 π–π 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.