Allylureas: Potent Argentophiles with a Marked Propensity to Form

Solomon W. Kelemu and Peter J. Steel*. Department of Chemistry, University of Canterbury, Christchurch 8140, New Zealand. Cryst. Growth Des. , 2014, 1...
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Allylureas: Potent Argentophiles with a Marked Propensity to Form One-Dimensional Coordination Polymers Solomon W. Kelemu and Peter J. Steel* Department of Chemistry, University of Canterbury, Christchurch 8140, New Zealand S Supporting Information *

ABSTRACT: 1,3-Diallylurea and tetraallylurea react with various silver salts to consistently generate one-dimensional coordination polymers in which the allyl arms and urea oxygen atoms are coordinated to silver atoms. Most commonly, ladderlike assemblies are produced.

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Structural Database10 revealed that no metal complexes of either of these ligands have been reported. We now show that both these ligands have a strong affinity for silver(I) and consistently assemble into one-dimensional (1D) coordination polymers in which (usually) all available allyl arms and the urea oxygen strongly bind to silver.

INTRODUCTION Metallosupramolecular chemistry1 uses combinations of bridging organic ligands and metal atoms to self-assemble discrete and polymeric species with various topologies.2 Coordination polymers of varying dimensionality have been the subject of much study over the last two decades.3 Within this field, silver(I) has proven to be particluarly popular as a metal for engineering the assembly of coordination polymers of varying dimensionality.4 For some years now, we have championed the use of the silver− alkene interaction as a useful synthon in metallosupramolecular chemistry.5 For example, we recently reported the synthesis and crystal structures of three silver complexes of triallylisocyanurate (1) (Scheme 1), in which we showed that the ligand

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RESULTS AND DISCUSSION Ligand 3 was prepared in 63% yield from commercially available 2 by reaction with allyl bromide in the presence of sodium hydride in refluxing THF. Potential ligands 2 and 3 were each then reacted with a variety of silver(I) salts. Five such reactions furnished crystals suitable for single crystal X-ray structure determination. The complex (4) [Ag(2)(OTf)]n from reaction with silver triflate crystallizes in the triclinic space group P1̅. The asymmetric unit contains one full ligand molecule, one silver atom, and a coordinated triflate counteranion, revealing a 1:1 M:L (metal:ligand) ratio. One of the allyl arms and the urea oxygen coordinate with silver, while the other allyl arm is noncoordinated and disordered over two sites with dominant position occupancy of 60% (Figure 1). The silver atom is five-coordinate, binding to one allyl group, two urea oxygens from different ligands, and two oxygens from different triflates. The geometry of the silver atom is intermediate between trigonal bipyramidal and square pyramidal, with a τ5 value11 of 0.44. The urea oxygen bridges two silver atoms separated by a distance of 3.768(1) Å and symmetry-related triflates bridge two silvers separated by 5.770(1) Å. As a result, the structure grows into a 1D coordination polymer, a section of which is shown in Figure 2. Silver-based 1D coordination

Scheme 1

consistently used only two of its three allyl arms for coordination.6 The coordinating subunit of this structure is represented by 1,3-diallylurea (2), which we decided to investigate as a ligand itself, along with the more heavily armed ligand tetraallylurea (3). Ureas have long been recognized as useful supramolecular synthons for crystal engineering,7 due to their propensity to form intermolecular hydrogen bonds. Ligands containing urea subunits have found use in many applications, such as anion binding and recognition,8 including examples of silver complexes.9 Despite the fact that 2 is commercially available, and 3 is readily prepared from it, a search of the Cambridge © 2014 American Chemical Society

Received: November 24, 2013 Revised: January 19, 2014 Published: January 24, 2014 1245

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Figure 3. One of the two Ag2L2 units in the asymmetric unit in the Xray crystal structure of complex 5. Atoms in adjacent asymmetric units are shown with broken bonds. All hydrogen atoms and the noncoordinated tetrafluoroborate counteranions have been omitted for clarity. Selected bond lengths (Å): Ag1−O1, 2.425(2); Ag1−O2, 2.400(2); Ag1−C6,C7, 2.261(3); Ag1−C8,C9, 2.285(3); Ag2−O1, 2.412(2); Ag2−C1,C2, 2.250(3); Ag2−O2A, 2.406(2); Ag2− C13,C14, 2.266(3).

Figure 1. The asymmetric unit in the X-ray crystal structure of complex 4. Atoms in adjacent asymmetric units and the minor component of the disordered allyl arm are shown with broken bonds. All hydrogen atoms have been omitted for clarity. Selected bond lengths (Å) and angles (deg) (note that CX,CY represents the midpoint of the bond between CX and CY): Ag1−O1 2.495(1), Ag1− O1A 2.315(1), Ag1−O2 2.411(1), Ag1−O3A 2.586(1), Ag1−C1,C2 2.295(2), O1−Ag1−O1A 76.9(4), Ag1−O1−Ag1A 103.1(4), O1− Ag1−O2 78.6(4), O1−Ag1−O3A 158.0(4), O1−Ag1−C1,C2 93.1(2), O2−Ag1−O1A 94.9(4), O2−Ag1−O3A 92.1(4), O2−Ag1−C1,C2 129.5(2), O1A−Ag1−C1,C2 131.9(2), O3A−Ag1−C1,C2 108.0(2).

independent silver atoms and the structure grows into a 1D coordination polymer. All four independent silver atoms are four-coordinate, being bound to two allyl groups and two oxygen atoms from different ligands. The geometries are all seesaw-shaped, with τ4 values14 falling in the range of 0.71−0.74. The silver atoms are separated by distances of 4.458(1) and 4.456(1) Å for the two independent units. These both extend into helical 1D coordination polymers, one of which is shown in Figure 4. Within these

Figure 2. A section of the 1D polymeric structure of complex 4.

polymers have been particularly well-studied in recent years,4 including examples involving organometallic 1D polymers.12 Within the polymer chain, ligand 2 uses one allyl arm and the carbonyl oxygen to chelate to one silver atom. The carbonyl oxygen also bridges to a second silver atom; thus, the ligand is both chelating and bridging (i.e., ambivergent).13 The chain consists of silver atoms linked by alternating pairs of triflates and diallylurea bridges. Since the urea oxygen atom is bonded to two silver atoms, there is no possibility of it being involved in the N−H···O hydrogen bonding commonly observed with other urea derivatives.7 Instead, one of the two N−H hydrogens is involved in a relatively strong hydrogen bond to the noncoordinated oxygen of the triflate group, with a N···O separation of 2.898(2) Å. Attempts to prepare single crystals of a complex of ligand 2 with silver(I) perchlorate invariably led to highly twinned crystals that failed to furnish useful diffraction data. The complex (5) [Ag(2)(BF4)]n, obtained by reaction of 2 with silver(I) tetrafluoroborate, crystallizes in the monoclinic space group P21/c, with the asymmetric unit containing four full molecules of 2, four silver(I) atoms, and four noncoordinated tetrafluoroborate counteranions, one of which is disordered. There are two independent Ag2L2 units, one of which is shown in Figure 3. This time both allyl arms of the ligand are coordinated with silver atoms through the alkene functional groups, helped by the fact that, unlike triflate, the tetrafluoroborate anion has a very weak affinity for silver. This results in ligand 2 forming two chelate rings. Once again, the urea carbonyl oxygen bridges two

Figure 4. Ball-and-stick (top) and space-filling (bottom) representations of the single-stranded helical chain of complex 5.

helical chains, the ligand acts in a tetradentate manner using all available donors. The twist required to generate the helical assembly is provided by the ligand adopting an “S-shaped” conformation. The complex (6) [Ag2(3)(ClO4)2]n, formed by reaction of tetraallylurea (3) with silver(I) perchlorate, crystallizes in the orthorhombic space group P21212. The complex has a 2:1 M:L stoichiometry, and the asymmetric unit contains half a molecule of 3, one silver atom, and a coordinated perchlorate anion (Figure 5). The silver atom is four-coordinate being bound to two allyl arms of different ligands, one urea oxygen atom, and one oxygen atom from the perchlorate counterion. The geometry is close to trigonal pyramidal with a τ4 value of 0.81. The Ag−O bond distance to the urea oxygen [2.568(1) Å] is relatively long, possibly because the oxygen uses both lone pairs for coordination. 1246

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Figure 8. A section of the 1D polymeric structure of complex 7. Hydrogen atoms and the minor component of the disordered triflate anion are not shown.

Figure 5. The asymmetric unit in the X-ray crystal structure of complex 6. Atoms in adjacent asymmetric units are shown with broken bonds. Selected bond lengths (Å) and angles (deg): Ag1−C1,C2, 2.340(2); Ag1−O5, 2.568(1); Ag1−O1, 2.410(1); Ag1−C6A,C7A, 2.309(2); C1,C2−Ag1−O5, 85.3(2); C1,C2−Ag1−O1, 117.3(2); O5−Ag1−O1, 86.0(4); C1,C2−Ag1−C6A,C7A, 128.7(2); O5− Ag1−C6A,C7A, 113.6(2); O1−Ag1−C6A,C7A, 111.5(2).

Figure 9. Schematic representation of the binding modes observed in complex 6 (top) and 7 (bottom).

Figure 6. A section of the 1D polymeric structure of complex 6.

Figure 10. The asymmetric unit in the X-ray crystal structure of complex 8. Atoms in adjacent asymmetric units are shown with broken bonds. The minor component of the disordered tetrafluoroborate and CH hydrogen atoms have been omitted for clarity. Selected bond lengths (Å): Ag1−C1,C2, 2.329(2); Ag1−O1, 2.574(1); Ag1−O2, 2.277(2); Ag1−C6A,C7A, 2.309(2); C1,C2−Ag1−O1, 81.8(2); C1,C2−Ag1−O2, 116.6(2); O1−Ag1−O2, 89.1(2); C1,C2−Ag1− C6A,C7A, 128.9(2); O1−Ag1−C6A,C7A, 111.9(2); O2−Ag1− C6A,C7A, 112.7(2).

Figure 7. The asymmetric unit in the X-ray crystal structure of complex 7. Atoms in adjacent asymmetric units are shown with broken bonds. All hydrogen atoms have been omitted for clarity. Selected bond lengths (Å): Ag1−C1,C2, 2.248(4); Ag1−O3, 2.314(2); Ag1− O4, 2.345(3); Ag1−O10, 2.593(4); Ag2−O3, 2.514(2); Ag2−O5, 2.372(3); Ag2−O6A, 2.443(3); Ag2−C6A,C7A, 2.276(3); Ag2−O7A, 2.501(2).

The ligand lies on a 2-fold rotation axis that passes through the carbonyl group, and it uses all four allyl arms to coordinate to four different silver atoms, two of which are also bridged by the urea oxygen atom. As a result, the structure extends into a 1D ladderlike coordination polymer, a section of which is shown in Figure 6. This consists of pairs of silver atoms bridged by a urea oxygen atom with a separation of 4.230(1) Å, which are linked to the next pair by coordination through the two arms of a diallylamino group, separated by 7.854(1) Å, the length of the c axis. Complex (7) [Ag4(3)(OTf)4]n, formed by reaction of 3 with silver(I) triflate, crystallizes in the monoclinic space group C2/c

Figure 11. A section of the 1D polymeric structure of complex 8.

and has a 4:1 M:L stoichiometry. The asymmetric unit contains half a molecule of 3, two silver atoms, and two coordinated triflate counteranions, one of which has a disordered CF3 group (Figure 7). The two independent silver atoms are separated by 3.784(1) Å, being bridged by two triflates using one and two oxygens, respectively. One silver atom is five-coordinate being bonded to one allyl arm, one carbonyl oxygen atom, and an oxygen of three different triflates, and has geometry intermediate 1247

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reflections collected independent reflections completeness data/restraints/parameters goodness-of-fit on F2 final R indexes [I ≥ 2σ(I)] final R indexes (all data)

5 C14H24B2N4O2F8Ag2 669.73 113 monoclinic P21/c 19.3527(8) 13.8767(5) 18.9763(7) 90 118.192(2) 90 4491.6(3) 8 1.981 1.828 2624 0.9 × 0.28 × 0.18 2.38 to 62.6° −28 ≤ h ≤ 28, −20 ≤ k ≤ 20, −27 ≤ l ≤ 27 126314 14560[R(int) = 0.0680] 99.1 14560/0/599 1.178 R1 = 0.0375, wR2 = 0.0900 R1 = 0.0441, wR2 = 0.0925

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C8H12N2O4F3SAg 397.13 110 triclinic P1̅ 8.0040(2) 8.3349(2) 11.4974(3) 84.431(1) 88.860(1) 62.795(1) 678.69(3) 2 1.943 1.684 392 0.40 × 0.34 × 0.16 5.52 to 50.1° −9 ≤ h ≤ 9, −9 ≤ k ≤ 9, −13 ≤ l ≤ 13 10743 2394[R(int) = 0.0334] 99.8 2394/0/186 1.042 R1 = 0.0172, wR2 = 0.0414 R1 = 0.0180, wR2 = 0.0418

complex

empirical formula formula weight temperature (K) crystal system space group a (Å) b (Å) c (Å) α (deg) β (deg) γ (deg) volume (Å3) Z ρcalc (mg mm−3) μ (mm−1) F(000) crystal size (mm3) 2θ range for data collection index ranges

Table 1. Crystal Data and Structure Refinements for 4−8 6 C13H20N2O9Cl2Ag2 634.95 110 orthorhombic P21212 8.3985(3) 15.0933(5) 7.8538(2) 90 90 90 995.56(5) 2 2.118 2.284 624 0.55 × 0.47 × 0.28 5.18 to 55.0° −10 ≤ h ≤ 10, −19 ≤ k ≤ 19, −10 ≤ l ≤ 10 42471 2285[R(int) = 0.0288] 100 2285/0/129 1.237 R1 = 0.0123, wR2 = 0.0330 R1 = 0.0144, wR2 = 0.0332

7 C17H22N2O14F12S4Ag4 1266.09 112 monoclinic C2/c 24.2984(7) 11.5154(3) 15.6844(4) 90 124.665(1) 90 3609.6(2) 4 2.330 2.492 2440 0.72 × 0.52 × 0.4 5.22 to 50.1° −28 ≤ h ≤ 28, −13 ≤ k ≤ 13, −18 ≤ l ≤ 18 33211 3193[R(int) = 0.0306] 99.9 3193/0/256 1.063 R1 = 0.0287, wR2 = 0.0704 R1 = 0.0319, wR2 = 0.0729

8 C13H28B2N2O5F8Ag2 681.73 113 orthorhombic Fdd2 18.4679(5) 31.8923(9) 7.8966(2) 90 90 90 4651.0(2) 8 1.947 1.774 2688 0.68 × 0.58 × 0.38 5.1 to 55.0° −23 ≤ h ≤ 23, −41 ≤ k ≤ 41, −10 ≤ l ≤ 10 31237 2665[R(int) = 0.0307] 99.9 2665/1/191 1.115 R1 = 0.0142, wR2 = 0.0345 R1 = 0.0145, wR2 = 0.0346

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between trigonal bipyramidal and square pyramidal with a τ5 value of 0.49. The second is four-coordinate with coordination to one alkene functional group, one carbonyl oxygen atom, one triflate oxygen, and a water molecule, and has a seesaw geometry with a τ4 value of 0.71. Once again the structure extends into a ladderlike 1D polymer (Figure 8) that propagates along the b axis about a 2-fold rotation axis and within which the ligand bridges silver atoms separated by 7.741(1) Å. The structure combines some of the features of complexes 4 and 6. As in complex 6, ligand 3 uses all available binding sites to bridge four silver atoms using the four allyl arms and the urea oxygen. The chain also contains subunits of four silver atoms bridged by two tridentate and two bidentate triflate anions. The relationship between complexes 6 and 7 is shown in Figure 9, which shows that ligand 3 adopts the same bridging mode in both structures. However, in complex 6 there is a continuous chain of bridging ligands, whereas in complex 7 these are interrupted by the multidentate triflate bridges. Finally, ligand 3 was reacted with silver tetrafluoroborate to produce a complex (8) [Ag2(3)(BF4)2(H2O)2]n with a 2:1 M:L stoichiometry. It crystallizes in the orthorhombic space group Fdd2, with an asymmetric unit comprising half a molecule of 3, one silver atom, a disordered noncoordinated tetrafluoroborate anion, a coordinated water molecule, and a noncoordinated water molecule, as shown in Figure 10. The silver atom is fourcoordinate binding to two olefinic groups, the carbonyl oxygen atom, and a water molecule and has a trigonal pyramidal shape with a τ4 value of 0.82. Complex 8 is also a 1D polymer that has a very similar connectivity to complex 6, with the ligand bridging four silver atoms using all available donors and the chain lying on a 2-fold rotation axis (Figure 11). The ligand separates silver atoms at a distance of 7.897(1) Å, slightly longer than in the other two complexes. The difference between complexes 6 and 8 is that the coordinated perchlorate anion in complex 6 has been replaced by a coordinated water molecule in 8, due to the low affinity of tetrafluoroborate for silver. Although the connectivity is almost identical in complexes 6 and 8, the presence of the water molecules plays an active role in the crystal packing of complex 8. There exists a complex network of hydrogen bonds that interconnects the polymer chains, the water molecules, and the tetrafluoroborate anions in a 2D array. All four OH hydrogen atoms are involved in relatively strong hydrogen bonds to either oxygen or fluorine atoms with D···A distances lying in the range of 2.693(2)−2.848(2) Å.

refluxed for two days. The reaction was cooled to room temperature and residual NaH was quenched with 30 mL of 1 M aqueous NH4Cl solution. The organic layer was extracted with 3 × 40 mL of diethyl ether. The ethereal extract was washed with water and brine and dried over MgSO4. Evaporation of diethyl ether under reduced pressure gave an impure white oily liquid. Purification of the crude product with silica gel column chromatography, using 30:70 ethyl acetate:petroleum ether, gave 3 as a red brown oily liquid (0.69 g, 63%). 1H NMR (300 MHz, CDCl3): δ 3.71 (8H, d, J = 5.7 Hz, H2), 5.10−5.16 (8H, m, H4), 5.72−5.83 (4H, m, H3). 13C NMR (75 MHz, CDCl3): δ 50.40, C2; 117.31, C4; 134.22, C3; 164.66, C1. IR(cm−1): 3079, 3009, 2982, 2927, 2860, 1847, 1738, 1643, 1462, 1433, 1404, 1360, 1278, 1230, 1196, 1132, 1048, 994, 921, 771, 732. ESI-MS: found MH+ = 221.1645; C13H21N2O requires MH+ = 221.1648. Synthesis of Complex 4 [Ag(2)(OTf)]n. 1,3-Diallylurea (0.028 g, 0.200 mmol) was dissolved in 1 mL of acetone and added to silver(I) triflate (0.103 g, 0.399 mmol) dissolved in 1 mL of acetone. The solution was left in darkness at room temperature and petroleum ether was allowed to diffuse into the solution. This enabled the isolation of colorless crystals suitable for single crystal X-ray structure analysis. Yield: 0.025 g, 31%. Mp: 119−121 °C. IR (cm−1): 3330, 2983, 2865, 1627, 1590, 1419, 1250, 1173, 1047, 993, 918, 766, 653. Elemental anal. Found: C, 24.40; H, 2.99; N, 6.95. Calcd for C7H12N2O·AgSO3CF3: C, 24.20; H, 3.05; N, 7.05. Synthesis of complex 5 [Ag(2)(BF4)]n. 1,3-Diallylurea (0.014 g, 0.100 mmol) was dissolved in 1 mL of acetone and added to silver(I) tetrafluoroborate (0.020 g, 0.100 mmol) dissolved in 1 mL of acetone. The solution was left in darkness at room temperature, and petroleum ether was allowed to diffuse into the solution. This enabled the isolation of colorless crystals suitable for single crystal X-ray structure analysis. Yield: 0.026 g, 76%. Mp: 137−139 °C. IR (cm−1): 3079, 2924, 2850, 1646, 1569, 1496, 1457, 1364, 1302, 1233, 1007, 963, 778, 765, 639. Elemental Anal. Found: C, 24.98; H, 3.99; N, 8.75. Calcd for C7H12N2O·AgBF4: C, 25.11; H, 3.61; N, 8.37. Synthesis of Complex 6 [Ag2(3)(ClO4)2]n. Tetraallylurea (0.022 g, 0.100 mmol) was dissolved in 1 mL of acetone and added to a solution of silver(I) perchlorate (0.042 g, 0.200 mmol) in 1 mL acetone. The solution was left in darkness at room temperature and diethyl ether was allowed to diffuse into the solution. This enabled the isolation of colorless crystals suitable for single crystal X-ray structure determination. Yield: 0.050 g, 78%. Mp: 139−141 °C. IR (cm−1): 3082, 2989, 2852, 1642, 1605, 1571, 1476, 1411, 1370, 1251, 1092, 1032, 943, 920, 764, 727, 615. Elemental Anal. Found: C, 24.95; H, 3.13; N, 4.44. Calcd for C13H20N2O·2AgClO4: C, 24.59; H, 3.17; N, 4.41. Synthesis of Complex 7 [Ag4(3)(OTf)4]n. Tetraallylurea (0.022 g, 0.100 mmol) was dissolved in 1 mL of acetone and was added to silver(I) triflate (0.051 g, 0.200 mmol) also dissolved in 1 mL acetone. The solution was left in darkness at room temperature, where diethyl ether was allowed to diffuse into the solution. This enabled the isolation of colorless crystals suitable for single crystal X-ray structure analysis. Yield: 0.034 g, 54%. Mp: 59−61 °C. IR (cm−1): 3392, 3078, 2989, 2854, 1647, 1600, 1567, 1481, 1424, 1365, 1225, 1160, 1025, 962, 927, 764, 724, 633. Elem. Anal. Found: C, 16.56; H, 1.95; N, 2.36. Calcd for C13H20N2O·4Ag(SO3CF3): C, 16.36; H, 1.62; N, 2.24. Synthesis of Complex 8 [Ag2(3)(BF4)2(H2O)2]n. Tetraallylurea (0.022 g, 0.100 mmol) was dissolved in 1 mL of acetone and added to a solution of silver(I) tetrafluoroborate (0.039 g, 0.200 mmol) in acetone. The solution was left in darkness at room temperature and diethyl ether was allowed to diffuse into the solution. This enabled the isolation of colorless crystals suitable for single crystal X-ray structure analysis. Yield: 0.036 g, 59%. Mp: 85−87 °C. IR (cm−1): 3079, 2924, 2852, 1647, 1596, 1486, 1418, 1364, 1258, 1159, 1013, 980, 927, 767, 727, 612. Elemental Anal. Found: C, 25.21; H, 3.76; N, 4.47. Calcd for C13H20N2O·2AgBF4·H2O: C, 24.88; H, 3.53; N, 4.46. X-ray Crystallography. X-ray crystallographic data collection was carried out with a Bruker APEXII instrument, using graphitemonochromated Mo Kα (λ = 0.71073 Å) radiation. All structures were solved using direct methods with SHELXS and refined on F2 using all data by full matrix least-squares procedures with SHELXL.15 All nonhydrogen atoms were refined with anisotropic displacement

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CONCLUSION Ligand 2 forms 1:1 M:L complexes with silver salts, which were shown to be a 1D polymeric ladderlike assembly with silver triflate and a single-stranded helix with silver tetrafluoroborate. Reaction of ligand 3 consistently produces ladderlike 1D polymers using all available binding sites of the ligand, irrespective of the counterion. There are no unusual features in the crystal packing and the bond lengths of the coordinated CC bonds show no correlation to the environment of the attached silver atoms.

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EXPERIMENTAL SECTION

Synthesis of Ligand 3. A mixture of 1,3-diallylurea (0.70 g, 5 mmol) and NaH (0.48 g, 20 mmol) was stirred in dry THF (50 mL) at 0 °C. Allylbromide (0.91 mL, 10.5 mmol) was added dropwise to the mixture, which was then warmed to room temperature and 1249

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parameters. Hydrogen atoms were included in calculated positions with isotropic displacement parameters 1.2 or 1.5 times the isotropic equivalent of their carrier atoms. Experimental details are listed in Table 1.

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ASSOCIATED CONTENT

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AUTHOR INFORMATION

(c) Dawn, S.; Salpage, S. R.; Smith, M. D.; Sharma, S. K.; Shimizu, L. S. Inorg. Chem. Commun. 2012, 15, 88. (d) Braga, D.; d’Agostino, S.; D’Amen, E.; Grepioni, F.; Genovese, D.; Prodi, L.; Sgarzi, M. Dalton Trans. 2013, 42, 16949. (10) Allen, F. H. Acta Crystallogr., Sect. B 2002, 58, 380. (11) Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349. (12) (a) Dong, Y.-B.; Jin, G.-X.; Smith, M. D.; Huang, R.-Q.; Tang, B.; zur Loye, H.-C. Inorg. Chem. 2002, 41, 4909. (b) Munakata, M.; Ning, G. L.; Suenaga, Y.; Kuroda-Sowa, T.; Maekawa, M.; Ohta, T. Angew. Chem., Int. Ed. 2000, 39, 4555. (c) Cheng, P.-S.; Marivel, S.; Zang, S.-Q.; Gao, G.-G.; Mak, T. C. W. Cryst. Growth Des. 2012, 12, 4519. (d) Li, B.; Wang, W.-K.; Zang, S.-Q.; Mak, T. C. W. J. Organomet. Chem. 2013, 745−746, 173. (e) Munakata, M.; Wen, M.; Suenaga, Y.; Kuroda-Sowa, T.; Maekawa, M.; Anahata, M. Polyhedron 2001, 20, 2321. (f) Ortiz, A. M.; Gómez-Sal, P.; Flores, J. C.; de Jesús, E. Organometallics 2014, 33, 600. (g) Munakata, M.; Wu, L. P.; Ning, G. L.; Kuroda-Sowa, T.; Maekawa, M.; Suenaga, Y.; Maeno, N. J. Am. Chem. Soc. 1999, 121, 4968. (h) Ning, G. L.; Munakata, M.; Wu, L. P.; Maekawa, M.; Suenaga, Y.; Kuroda-Sowa, T.; Sugimoto, K. Inorg. Chem. 1999, 38, 5668. (i) Mak, T.; Zhao, C. W. L. Chem.−Asian J. 2007, 2, 456. (j) Sabounchei, S. J.; Bagherjeri, F. A.; Mozafari, Z.; Boskovic, C.; Gable, R. W.; Karamian, R.; Asadbegy, M. Dalton Trans. 2013, 42, 2520. (k) Zhang, T.; Song, H.; Dai, X.; Meng, M. Dalton Trans. 2009, 7688. (l) Akhbari, K.; Morsali, A. Cryst. Growth Des. 2007, 7, 2024. (m) Zhang, Q.-L.; Zhu, B.-X.; Zhang, Y.-Q.; Tao, Z.; Clegg, J. K.; Lindoy, L. F.; Wei, G. Cryst. Growth Des. 2011, 11, 5688. (n) Hau, S. C. K; Mak, T. C. W. Chem.Eur. J. 2013, 19, 5387. (13) Fitchett, C. M.; Steel, P. J. Polyhedron 2007, 26, 400. (14) Yang, L.; Powell, D. R.; Houser, R. P. Dalton Trans. 2007, 955. (15) Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112.

S Supporting Information *

CIF files giving crystallographic data for 4−8. This material is available free of charge via the Internet at http://pubs.acs.org. Corresponding Author

*E-mail: [email protected]. Notes

The authors declare no competing financial interest.

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ACKNOWLEDGMENTS The authors thank the University of Canterbury, College of Science, for a doctoral scholarship and the RSNZ Marsden fund for generous financial support.

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dx.doi.org/10.1021/cg4017678 | Cryst. Growth Des. 2014, 14, 1245−1250