Electronic supplementary information (ESI) · 2013. 10. 25. · 1 Electronic supplementary information (ESI) Construction of N,N -di(3-pyridyl)adipoamide-based Zn(II) and Cd(II) coordination

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Electronic supplementary information (ESI)

Construction of N,N-di(3-pyridyl)adipoamide-based Zn(II)

and Cd(II) coordination polymers by tuning the isomeric

effect of polycarboxylate ligands

Pei-Chi Cheng,a Ming-Hao Wu,a Ming-Yuan Xie,a Wun-Jhih Huang,a

Hsiu-Yi He,a Tsung-Tai Wu,a Yang-Chih Lo,a

Davide M. Proserpiob,c and Jhy-Der Chen*,a

aDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li,

Taiwan, R.O.C. bUniversità degli Studi di Milano, Dipartimento di Chimica, Via Golgi 19,

20133 Milano, Italy cSamara Center for Theoretical Materials Science (SCTMS), Samara State

University, Ac. Pavlov St. 1, Samara 443011, Russia

Electronic Supplementary Material (ESI) for CrystEngCommThis journal is © The Royal Society of Chemistry 2013

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Fig. S1. TGA curves for complexes 1 – 4.


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Fig. S2. TGA curves for complexes 5 – 8.


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Fig. S3. The 2D nets of 1 are linked by N-H---O and O-H---O hydrogen

bonds.

Symmetry transformations used to generate equivalent atoms: (A) x+1, y, z (B) x+1/2,

-y+1/2, z-1/2 (C) -x+2, -y, -z (D) -x+2, -y+1, -z

Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and <DHA > 110 deg.

D-H d(D-H) d(H..A) <DHA d(D..A) A

N2-H2A 0.860 1.969 166.07 2.812 O7 [ -x+2, -y+1, -z ]

O7-H7OB 0.874 1.886 175.55 2.758 O3

O7-H7OA 0.792 1.987 162.62 2.753 O5 [ x+1, y, z ]

O6-H6OB 0.770 2.021 175.29 2.789 O5 [ x+1/2, -y+1/2, z-1/2 ]

O6-H6OB 0.770 2.578 127.00 3.103 O4 [ x+1/2, -y+1/2, z-1/2 ]

O6-H6OA 0.899 1.873 173.09 2.768 O1 [ -x+2, -y, -z ]


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Fig. S4. The adjacent ladder chains of 3 are linked by the N-H---O and

O-H---O hydrogen bonds.

Symmetry transformations used to generate equivalent atoms: (A) -x+2, -y+1, -z+2

(B) -x+5/2, y-1/2, -z+5/2 (C) x, y-1, z (D) -x+2, -y, -z+2 (E) -x+5/2, y+1/2, -z+5/2

Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and <DHA > 110 deg.

D-H d(D-H) d(H..A) <DHA d(D..A) A

N2-H2A 0.860 2.058 161.28 2.886 O5 [ x-1/2, -y+1/2, z+1/2 ]

O6-H6B 0.867 1.835 171.95 2.696 O9

O6-H6C 0.757 1.966 172.77 2.719 O4 [ -x+2, -y+1, -z+2 ]

O7-H7D 0.673 2.233 164.51 2.886 O10 [ -x+5/2, y-1/2, -z+5/2 ]

O7-H7E 0.762 1.982 172.28 2.738 O3 [ -x+5/2, y-1/2, -z+5/2 ]

O8-H8D 0.805 1.935 154.65 2.684 O3 [ x, y-1, z ]

O8-H8E 0.798 2.062 161.74 2.830 O10

O9-H9D 0.928 1.835 167.94 2.749 O4 [ x, y-1, z ]

O9-H9E 0.785 2.180 168.26 2.952 O8 [ -x+2, -y, -z+2 ]

O10-H10B 0.779 1.998 155.79 2.727 O5

O10-H10C 0.884 1.981 143.39 2.742 O1 [ -x+5/2, y+1/2, -z+5/2 ]


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Fig. S5. The 1D double zigzag chains of 4 are linked by N-H---O

interactions.


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Fig. S6. The 2D nets of 5 are linked by π-π and N-H---O interactions.


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Fig. S7. Emission spectra of (a) H3BTC ligands, (b) complexes 1 – 4, (c)

complexes 5 – 8 in the solid.

(a)

(b)

(c)


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Fig. S8. The PXRD patterns of (a) simulated single-crystal X-ray data of

compound 1, (b) bulk materials as synthesized for compound 1.


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(a)

(b)




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Table 2. Selected bond distances (Å) and angles (o) for 1 – 8.

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Zn-N(1) 2.128(2) Zn-N(3A) 2.162(2)

Zn-O(2) 2.021(2) Zn-O(4A) 2.032(2)

Zn-O(6) 2.042(2)

N(1)-Zn-N(3A) 166.02(9) O(4A)-Zn-N(1) 88.35(8)

O(2)-Zn-N(1) 95.00(9) O(4A)-Zn-N(3A) 77.69(8)

O(2)-Zn-N(3A) 96.27(9) O(4A)-Zn-O(6) 112.43(9)

O(2)-Zn-O(4A) 146.20(9) O(6)-Zn-N(1) 92.27(10)

O(2)-Zn-O(6) 101.05(9) O(6)-Zn-N(3A) 93.65(10)

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Zn-N(1) 2.029(2) Zn-N(3) 2.014(2)

Zn-O(2) 2.278(2) Zn-O(3A) 1.959(2)

Zn-O(4) 2.099(2)

N(1)-Zn-O(2) 95.37(7) O(3A)-Zn-N(1) 113.97(7)

N(1)-Zn-O(4) 95.88(7) O(3A)-Zn-N(3) 136.10(7)

N(3)-Zn-N(1) 109.63(7) O(3A)-Zn-O(2) 96.36(7)

N(3)-Zn-O(2) 74.37(6) O(3A)-Zn-O(4) 100.98(7)

N(3)-Zn-O(4) 79.09(7) O(4)-Zn-O(2) 153.34(6)

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Zn-N(1) 2.155(2) Zn-N(3) 2.131(2)

Zn-O(2A) 2.066(2) Zn-O(6) 2.073(2)

Zn-O(7) 2.139(2) Zn-O(8) 2.265(2)

N(1)-Zn-O(8) 171.96(9) N(3)-Zn-N(1) 98.75(9)

N(3)-Zn-O(7) 87.25(10) N(3)-Zn-O(8) 86.55(9)

O(2A)-Zn-N(1) 88.74(8) O(2A)-Zn-N(3) 172.23(8)

O(2A)-Zn-O(6) 91.04(9) O(2A)-Zn-O(7) 91.18(9)

O(2A)-Zn-O(8) 85.79(8) O(6)-Zn-N(1) 92.61(9)

O(6)-Zn-N(3) 90.70(9) O(6)-Zn-O(7) 177.51(10)

O(6)-Zn-O(8) 93.37(9) O(7)-Zn-N(1) 86.31(10)

O(7)-Zn-O(8) 87.92(9)

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Cd-N(1) 2.367(2) Cd-N(4A) 2.353(2)

Cd-N(5) 2.351(2) Cd-O(3) 2.438(2)

Cd-O(5) 2.469(2) Cd-O(5B) 2.429(1)

Cd-O(7) 2.299(2)

N(1)-Cd-O(3) 96.54(7) N(1)-Cd-O(5) 86.19(6)

N(1)-Cd-O(5B) 87.28(6) N(4A)-Cd-N(1) 175.41(6)


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N(4A)-Cd-O(3) 88.04(7) N(4A)-Cd-O(5) 90.69(6)

N(4A)-Cd-O(5B) 88.51(5) N(5)-Cd-N(1) 89.59(6)

N(5)-Cd-N(4A) 92.33(6) N(5)-Cd-O(3) 67.64(6)

N(5)-Cd-O(5) 67.56(5) N(5)-Cd-O(5B) 138.10(6)

O(3)-Cd-O(5) 135.08(5) O(5B)-Cd-O(3) 154.17(6)

O(5B)-Cd-O(5) 70.54(5) O(7)-Cd-N(1) 87.97(7)

O(7)-Cd-N(4A) 93.14(7) O(7)-Cd-N(5) 141.18(7)

O(7)-Cd-O(3) 74.17(6) O(7)-Cd-O(5) 150.65(6)

O(7)-Cd-O(5B) 80.47(6)

Table 2. Selected bond distances (Å) and angles (o) for 1 – 9. (cont.)

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Zn-N(1) 2.034(2) Zn-O(3) 1.935(2)

Zn-N(3) 2.061(2) Zn-O(8A) 1.918(2)

N(1)-Zn-N(3) 101.58(8) O(8A)-Zn-N(1) 107.99(8)

O(3)-Zn-N(1) 123.26(8) O(8A)-Zn-N(3) 101.15(8)

O(3)-Zn-N(3) 106.85(8) O(8A)-Zn-O(3) 113.07(7)

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Cd(1)-N(1) 2.363(6) Cd(2)-N(4C) 2.470(6)

Cd(1)-N(8A) 2.410(6) Cd(2)-N(5) 2.350(6)

Cd(1)-O(5) 2.258(6) Cd(2)-O(7) 2.258(5)

Cd(1)-O(6) 2.619(6) Cd(2)-O(13B) 2.591(5)

Cd(1)-O(11) 2.215(6) Cd(2)-O(14B) 2.302(5)

Cd(1)-O(17) 2.299(5) Cd(2)-O(18) 2.310(5)

N(1)-Cd(1)-N(8A) 162.6(2) N(4C)-Cd(2)-O(13B) 86.03(19)

N(1)-Cd(1)-O(6) 89.43(19) N(5)-Cd(2)-N(4C) 164.1(2)

N(8A)-Cd(1)-O(6) 92.8(2) N(5)-Cd(2)-O(13B) 101.02(19)

O(5)-Cd(1)-N(1) 81.2(2) O(7)-Cd(2)-N(5) 103.2(2)

O(5)-Cd(1)-N(8A) 86.5(2) O(7)-Cd(2)-N(4C) 85.7(2)

O(5)-Cd(1)-O(6) 52.77(19) O(7)-Cd(2)-O(13B) 117.29(18)

O(5)-Cd(1)-O(17) 114.4(2) O(7)-Cd(2)-O(14B) 166.60(19)

O(11)-Cd(1)-N(1) 110.1(2) O(7)-Cd(2)-O(18) 94.7(2)

O(11)-Cd(1)-N(8A) 86.9(2) O(14B)-Cd(2)-N(4C) 84.3(2)

O(11)-Cd(1)-O(5) 146.6(2) O(14B)-Cd(2)-N(5) 88.6(2)

O(11)-Cd(1)-O(6) 95.03(19) O(14B)-Cd(2)-O(13B) 53.11(17)

O(11)-Cd(1)-O(17) 97.7(2) O(14B)-Cd(2)-O(18) 92.0(2)

O(17)-Cd(1)-N(1) 87.34(19) O(18)-Cd(2)-N(4C) 78.1(2)


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O(17)-Cd(1)-N(8A) 86.7(2) O(18)-Cd(2)-N(5) 88.0(2)

O(17)-Cd(1)-O(6) 167.2(2) O(18)-Cd(2)-O(13B) 143.10(19)

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Cd-N(1) 2.337(2) Cd-O(2) 2.298(1)

Cd-O(3) 2.495(1) Cd-O(5B) 2.340(1)

Cd-O(6A) 2.510(1) Cd-O(7A) 2.336(1)

Cd-O(8) 2.290(2)

N(1)-Cd-O(3) 90.92(6) N(1)-Cd-O(5B) 95.75(7)

N(1)-Cd-O(6A) 95.88(6) O(2)-Cd-N(1) 88.58(6)

O(2)-Cd-O(3) 54.46(4) O(2)-Cd-O(5B) 136.31(5)

O(2)-Cd-O(6A) 91.81(4) O(2)-Cd-O(7A) 145.28(5)

O(3)-Cd-O(6A) 145.46(4) O(5B)-Cd-O(3) 81.96(5)

O(5B)-Cd-O(6A) 130.60(4) O(7B)-Cd-N(1) 92.62(6)

O(7A)-Cd-O(3) 160.00(5) O(7A)-Cd-O(5B) 78.10(5)

O(7A)-Cd-O(6A) 53.54(4) O(8)-Cd-N(1) 175.20(7)

O(8)-Cd-O(2) 88.33(6) O(8)-Cd-O(3) 90.26(6)

O(8)-Cd-O(5B) 89.01(6) O(8)-Cd-O(6A) 80.55(6)

O(8)-Cd-O(7A) 87.85(6)

Table 2. Selected bond distances (Å) and angles (o) for 1 – 9. (cont.)

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Zn(1)-N(1) 2.053(3) Zn(1)-O(2) 1.975(2)

Zn(1)-O(4A) 1.963(2) Zn(1)-O(6B) 2.170(3)

Zn(1)-O(7B) 2.252(3) Zn(2)-O(3) 2.090(2)

Zn(2)-O(3C) 2.090(2) Zn(2)-O(8) 2.150(3)

Zn(2)-O(8C) 2.150(3) Zn(2)-O(9) 2.063(4)

Zn(2)-O(9C) 2.063(4)

N(1)-Zn(1)-O(6B) 104.26(12) N(1)-Zn(1)-O(7B) 95.86(13)

O(2)-Zn(1)-N(1) 117.90(11) O(2)-Zn(1)-O(6B) 127.72(10)

O(2)-Zn(1)-O(7B) 86.72(11) O(4A)-Zn(1)-N(1) 97.24(11)

O(4A)-Zn(1)-O(2) 104.72(10) O(4A)-Zn(1)-O(6B) 98.76(11)

O(4A)-Zn(1)-O(7B) 155.87(12) O(6B)-Zn(1)-O(7B) 58.26(11)

O(3)-Zn(2)-O(8) 95.69(11) O(3)-Zn(2)-O(8C) 84.31(11)

O(3C)-Zn(2)-O(3) 180.00(9) O(3C)-Zn(2)-O(8) 84.31(11)

O(3C)-Zn(2)-O(8C) 95.69(11) O(8C)-Zn(2)-O(8) 180.00(17)

O(9)-Zn(2)-O(3) 94.64(12) O(9)-Zn(2)-O(3C) 85.36(12)


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O(9)-Zn(2)-O(8) 91.44(15) O(9)-Zn(2)-O(8C) 88.56(14)

O(9C)-Zn(2)-O(3) 85.36(12) O(9C)-Zn(2)-O(3C) 94.64(12)

O(9C)-Zn(2)-O(8) 88.56(14) O(9C)-Zn(2)-O(8C) 91.44(15)

O(9C)-Zn(2)-O(9) 180.00(13)

Symmetry transformations used to generate equivalent atoms:

(A) -x+3/2,y-1/2,-z+1/2 for 1; (A) -x+1,y+1/2,-z+1/2 for 2; (A) x,y-1,z for 3; (A)

x+1,y-1,z-1; (B) -x+3,-y,-z+1 for 4; (A) x+1/2,-y+3/2,z-1/2 for 5; (A) -x-2,y+1/2,-z;

(B) x+1,y,z; (C) -x+1,y-1/2,-z+1 for 6; (A) x,-y+3,z-1/2; (B) x,-y+2,z-1/2 for 7; (A)

x+1,y,z; (B) x+1/2,-y+1/2,z+1/2; (C) -x,-y,-z+2 for 8.


Electronic supplementary information (ESI) · 2013. 10. 25. · 1 Electronic supplementary information (ESI) Construction of N,N -di(3-pyridyl)adipoamide-based Zn(II) and Cd(II) coordination

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