Introduction 1 2 3 1 x y z 3 Fig. 1 Bacillus cereus 4  3 5 6 8 9 22 carboxylato 23 24 25 9 12 11 18 19 9 2 22 26 28 27 28 26 2 2 2 2 2 Fig. 2 2 2 2 2 2 2 2  Materials and methods 2 2 2 1 13 2 2 29 2 2 4 2 27 2 26 30 Benzyl bis(1-methylimidazol-2-yl)acetate 2 2 n 2 4 2 2 1 3 δ H 3 H 2 H H im H im H Ph 17 18 4 2  ν −1 m z + 2 2 2 3 2 2 2 2 1 2 δ J H 2 H 3 J H 2 H im H im 13 1 2 δ 22 26 8 4 ν −1 m/z + + + 2 2 2 2 1 2 δ J H 2 H 3 2 H H im H im 13 1 2 δ 11 13 4 2 ν −1 m z + + 2+ + + + 2 2 2 2 2 2 11 15 4 3 ν −1 2 2 2 2 2 1 2 δ J H 3 3 J 3 H 3 J H 3 2 J H 2 3 H 3 3 J H 3 3 J H 3 J H 2 im 13 1 3 δ 19 29 4 2 ν −1 m z 2+ + + 2+ + + + 2 2 2 2 2 2 2 2 1 3 δ H 3 H 2 H J H im J H im H Ph H Ph 13 1 3 δ 17 18 2 4 2 ν −1 m z + 2 2 2 2 2 2 2 24 26 8 8 2 2 ν −1 2 2 2 2 2 2 2 2 2 2 2 2  2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 λ 31 F 2 32 1 Table 1 2 2 2 2 2 2 2 2 2 2 2 2 Compound 2 2 2 2 2 2 2 2 2 2 2 2 Formula 11 15 4 3 19 29 4 2 17 18 2 4 2 9 12 2 4 24 26 8 8 2 2 FW 352.09 446.28 446.62 312.50 793.36 3 0.30 × 0.12 × 0.09 0.18 × 0.03 × 0.03 0.60 × 0.03 × 0.03 0.30 × 0.15 × 0.06 0.24 × 0.18 × 0.09 Crystal color Colorless Colorless Colorless Colorless Colorless Crystal system Orthorhombic Monoclinic Monoclinic Monoclinic Triclinic Space group P 1 1 1 Cc C c P 1 c  \documentclass[12pt]{minimal}
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\begin{document}$$P\bar{1}\;(\text{no. 2})$$\end{document} a 8.7159(1) 10.1766(2) 35.5761(4) 7.3547(1) 9.9634(7) b 10.1124(1) 23.8561(6) 7.4531(1) 14.9538(2) 12.0617(11) c 15.1177(2) 9.1995(2) 14.6106(2) 12.3489(2) 14.8889(9) α – – – – 113.021(3) β – 107.0078(14) 101.8858(5) 117.5968(6) 90.365(3) γ – – – – 102.513(3) V 1332.45(3) 2135.72(8) 3790.97(8) 1203.62(3) 1599.4(2) Z 4 4 8 4 2 D calc. −3 1.755 1.388 1.565 1.724 1.647 μ −1 2.056 1.296 1.597 2.461 1.580 Absorption correction Multiscan Multiscan Multiscan Multiscan Multiscan Absorption correction range 0.71–0.84 0.86–0.96 0.85–0.96 0.74–0.86 0.64–0.87 θ λ max −1 0.65 0.65 0.60 0.65 0.65 Reflections (measured/unique) 21,618/3,063 11,758/4,644 28,566/3,424 27,341/2,759 35,709/7,342 Parameters/restraints 241/0 251/2 237/0 193/0 438/0 I σ I 0.0182/0.0447 0.0312/0.0694 0.0309/0.0704 0.0306/0.0793 0.0389/0.0867 R1/wR2 (all reflections) 0.0190/0.0452 0.0384/0.0723 0.0512/0.0786 0.0389/0.0852 0.0540/0.0947 S 1.062 1.041 1.081 1.089 1.083 37 −0.006(7) 0.305(9) – – – e −3 −0.36/0.19 −0.27/0.41 −0.31/0.43 −0.54/1.23 −0.79/0.51 MIm 2 Pr iPrEtIm 2 Pr BnMIm 2 Ac 2 2 2 2 33 2 34 2 2 34 2 2 2 35 2 2 2 2 c 36 34 2 2 2 2 2 2 2 2 2 2 2 2 http://www.ccdc.cam.ac.uk Results 2 2 2 2 2 2 2 2 2 2 2 2 1 2 3 Fig. 3 1 2 2 2 a 2 b 2 2 c 2 2 Asterisks  2 2 2 2 2 2 2 2 2 + 4 + 2 3 2 2 30 3 2 2 2 2 2 2 2 2 2 4 II 2 2 27 2 27 ν as ν s −1 ν as ν s −1 ionic 38 2 2 + Fig. 4 2 2  2 2 2 2 1 2 2 5 2 Fig. 5 1 2 2  5 1 2 1 3 1 2 −1 ν as ν s −1 2 2 2 2 + 2 + 2 + 2 2+ 2 + 2 2 2 2 2 2 2 2 2 2 2 6 2 Fig. 6 2 2 c x y z  Table 2 2 2 Bond Bond length Angle Bond angle Angle Bond angle Zn1–N2 2.1203 (15) N4–Zn1–N2 88.05 (6) N2–Zn1–O1a 92.41 (5) Zn1–N4 2.0517 (14) N2–Zn1–O3 173.58 (5) O1a–Zn1–O3 82.24 (5) Zn1–O1a 1.9975 (11) O3–Zn1–N4 90.38 (5) N4–Zn1–Cl1 119.50 (4) Zn1–Cl1 2.2844 (4) O3–Zn1–Cl1 90.23 (4) Cl1–Zn1–O1a 130.40 (4) Zn1–O3 2.1860 (13) Cl1–Zn1–N2 95.97 (4) O1a–Zn1–N4 109.55 (5) x y z 2 c 2 2 2 26 27 39 τ 40 angles carboxylato tBu2,Me2 2 12 tBu2,Me2 tert 2 2 2 2 41 tBu,Me 2 4 11 tBu,Me tert- 2 2 P 1 1 1 2 2 7 3 2 2 Fig. 7 2 2 x y z x y z  Table 3 2 2 Donor–H···acceptor D–H H···A D···A D–H···A i 0.78 (3) 1.95 (3) 2.7307 (19) 176 (3) ii 0.84 (3) 2.31 (3) 3.1472 (15) 171 (3) x y z x y z 2 2 2 2 2 2 −1 ν as ν s −1 2 2 2 2 2 8 4 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 9 11 12 18 2 2 2 Fig. 8 2 x y z  Table 4 2 Bond Bond length Angle Bond angle Angle Bond angle Zn1–N2 2.038 (2) Cl1–Zn1–N2 116.85 (7) N2–Zn1–O1a 108.85 (8) Zn1–N4 2.045 (2) Cl1–Zn1–N4 112.12 (7) N4–Zn1–O1a 103.15 (9) Zn1–O1a 1.9628 (19) Cl1–Zn1–O1a 119.66 (6)   Zn1–Cl1 2.2146 (7) N2–Zn1–N4 91.90 (9)   x y  z 2 2 1 1 2 2 9 Fig. 9 1 2 2 3 a 2 2 b 2 2 c 2 2 d 2 2 Asterisks 2  1 2 9 2 2 2 1 2 2 2 3 2 2 2 + 2 2 2 2 + 3 2 3 3 + 2 2 2 2 3 9 2 2 2 1 2 2 2 2 2 + 2 2 2+ 2 2 10 thiolate 2 tert 2 2 2 H 42 43 2 2 2 2 2 2 2 Fig. 10 2 2 44  Attempted synthesis of a zinc bis(1-methylimidazol-2-yl)acetate complex 9 11 12 18 19 2 2 2 11 Fig. 11 2 2 bpa 2 2 2 2 2  2 2 2 45 39 2 2 46 2 2 2 2 2 2 2 12 2 2 2 2 2 2 2 2 2 2 12 2 Fig. 12 2 2 top 2 2 2 bottom 2 2 2 2 2  Reaction of [Zn(MIm2Pr)Cl] with sodium pyruvate: oxalate formation 2 2 2 2 1 13 2 2 2 + 2 2 2 + 2 Fig. 13 1 2 2 asterisk  2 2 13 2 2 2 2 2 2 2 2 2 + oxalato 2 2 2 2 2 4 2 2 2 2 2 2 2 2 −1 2 2 2 47 2 2 2 2 2 2 2 2 2 2 2 2 2 14 5 1 2 2 2 2 2 2 2 Fig. 14 2 2 2 2  Table 5 2 2 2 2 Bond Bond length Angle Bond angle Angle Bond angle Zn1–O31 2.258 (2) O11–Zn1–O31 89.48 (8) O21–Zn2–O41 90.33 (8) Zn1–O32 2.018 (2) O11–Zn1–O32 124.09 (9) O21–Zn2–O42 125.19 (8) Zn1–O11 1.9694 (19) O11–Zn1–N22b 108.91 (9) O21–Zn2–N12 109.08 (9) Zn1–N24b 2.046 (2) O11–Zn1–N24b 107.61 (9) O21–Zn2–N14 107.85 (9) Zn1–N22b 2.088 (2) O31–Zn1–O32 77.16 (9) O41–Zn2–O42 77.84 (8) Zn2–O41 2.233 (2) O31–Zn1–N22b 161.43 (9) O41–Zn2–N12 160.51 (8) Zn2–O42 2.0179 (19) O31–Zn1–N24b 87.69 (9) O41–Zn2–N14 87.24 (9) Zn2–O21 1.9630 (19) O32–Zn1–N22b 89.94 (8) O42–Zn2–N12 89.12 (8) Zn2–N12 2.089 (2) O32–Zn1–N24b 125.38 (9) O42–Zn2–N14 124.42 (9) Zn2–N14 2.052 (2) N22b–Zn1–N24b 89.06 (9) N12–Zn2–N14 88.34 (9) C31–O31 1.248 (4)   C41–O41 1.250 (3) C31d–O32 1.252 (4)   C41c–O42 1.254 (3) C31–C31d 1.544 (6)   C41–C41c 1.537 (6) x y z x y z x y z τ 40 10 48 2 2 2 2 2 2 2 15 Fig. 15 2 2 2 2  Discussion 2 2 2 27 28 26 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 2 16 2 2 2 2 2 Fig. 16 2 2 top 2 bottom  2 2 2 2 1 2 51 α α α Scheme 1 2  2 2 2 2 2 2 2 2 2 52 53 d 3 1 2 2 52 53 52 54 α 2 55 56 57 58 61 2 α 55 56 59 63 2 3 Conclusions 2 2 2 2 2 2 2