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A Anexos

A.1

Dados Cristalográficos

A.1.1

Ligante H4L1

Tabela A1 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o Ligante H4L1.

O1-H1 0,820(2) H1-O1-C1 109,5(2)

O1-C1 1,368(4) C8-N1-C14 109,6(2)

N1-C8 1,470(3) C8-N1-C7 110,0(2)

N1-C14 1,470(4) C14-N1-C7 112,5(2)

N1-C7 1,468(4) C9-N2-C13 117,1(3)

N2-C9 1,318(4) H2-C2-C3 120,3(4)

N2-C13 1,337(7) H2-C2-C1 120,4(4)

C2-H2 0,931(4) C3-C2-C1 119,3(4)

C2-C3 1,369(7) N1-C8-H8a 108,8(2)

C2-C1 1,391(5) N1-C8-H8b 108,8(2)

C8-H8a 0,970(3) N1-C8-C9 113,5(2)

C8-H8b 0,970(3) H8a-C8-H8b 107,8(3)

C8-C9 1,500(4) H8a-C8-C9 108,8(2)

C5-H5 0,930(4) H8b-C8-C9 108,9(2)

C5-C4 1,380(6) H5-C5-C4 119,4(4)

C5-C6 1,381(5) H5-C5-C6 119,5(3)

C20-C15 1,391(3) C4-C5-C6 121,1(3)

C20-O2 1,354(3) C15-C20-O2 118,5(2)

C20-C19 1,408(3) C15-C20-C19 120,0(2)

C3-H3 0,930(5) O2-C20-C19 121,5(2)

Anexos 146

Tabela A1 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o Ligante H4L1. (continuação)

C3-C4 1,363(8) C2-C3-H3 119,7(5)

C14-H14a 0,970(3) C2-C3-C4 120,7(4)

C14-H14b 0,969(3) H3-C3-C4 119,6(5)

C14-C15 1,502(3) N1-C14-H14a 108,9(2)

C4-H4 0,931(5) N1-C14-H14b 108,9(2)

C1-C6 1,388(4) N1-C14-C15 113,5(2)

C7-H7a 0,970(3) H14a-C14-H14b 107,8(3)

C7-H7b 0,970(3) H14a-C14-C15 108,8(2)

C7-C6 1,507(4) H14b-C14-C15 108,9(2)

C15-C16 1,383(4) C5-C4-C3 119,9(4)

C9-C10 1,366(5) C5-C4-H4 120,1(5)

O2-H2a 0,820(2) C3-C4-H4 120,0(5)

N3-C22 1,270(4) O1-C1-C2 116,9(3)

N3-C23 1,484(4) O1-C1-C6 122,2(3)

C16-H16 0,930(3) C2-C1-C6 120,9(3)

C16-C17 1,390(3) N1-C7-H7a 109,1(2)

C17-C18 1,371(4) N1-C7-H7b 109,1(2)

C17-C21 1,514(4) N1-C7-C6 112,6(2)

C19-C22 1,448(4) H7a-C7-H7b 107,9(3)

C19-C18 1,390(4) H7a-C7-C6 109,1(3)

C10-H10 0,931(4) H7b-C7-C6 109,1(3)

C10-C11 1,373(5) C20-C15-C14 120,5(2)

C22-H22 0,930(3) C20-C15-C16 117,9(2)

C18-H18 0,930(2) C14-C15-C16 121,6(2)

C11-H11 0,930(4) C5-C6-C1 118,0(3)

C11-C12 1,362(7) C5-C6-C7 121,3(3)

C13-H13 0,929(4) C1-C6-C7 120,5(3)

C13-C12 1,341(8) N2-C9-C8 116,7(3)

C12-H12 0,931(5) N2-C9-C10 121,7(3)

C23-H23a 0,970(3) C8-C9-C10 121,6(3)

C23-H23b 0,971(3) C20-O2-H2a 109,4(2)

C23-C23 1,486(5) C22-N3-C23 118,2(3)

Anexos 147

Tabela A1 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o Ligante H4L1. (continuação)

C21-H21a 0,961(3) C15-C16-H16 118,1(3)

C21-H21b 0,960(3) C15-C16-C17 123,8(3)

C21-H21C 0,960(3) H16-C16-C17 118,1(3)

C21-H21d 0,960(3) C16-C17-C18 116,9(3)

C21-H21e 0,961(4) C16-C17-C21 121,7(3)

C21-H21f 0,960(3) C18-C17-C21 121,5(3)

O1-H1 0,820(2) C20-C19-C22 121,1(3)

O1-C1 1,368(4) C20-C19-C18 119,2(3)

N1-C8 1,470(3) C22-C19-C18 119,6(3)

N1-C14 1,470(4) C9-C10-H10 120,0(3)

N1-C7 1,468(4) C9-C10-C11 120,0(3)

N2-C9 1,318(4) H10-C10-C11 119,9(4)

N2-C13 1,337(7) N3-C22-C19 123,0(3)

C2-H2 0,931(4) N3-C22-H22 118,5(3)

C2-C3 1,369(7) C19-C22-H22 118,5(3)

C2-C1 1,391(5) C17-C18-C19 122,2(3)

C8-H8a 0,970(3) C17-C18-H18 118,9(3)

C8-H8b 0,970(3) C19-C18-H18 118,9(3)

C8-C9 1,500(4) C10-C11-H11 120,8(4)

C5-H5 0,930(4) C10-C11-C12 118,3(4)

C5-C4 1,380(6) H11-C11-C12 120,8(4)

C5-C6 1,381(5) N2-C13-H13 117,7(5)

C20-C15 1,391(3) N2-C13-C12 124,8(5)

C20-O2 1,354(3) H13-C13-C12 117,6(5)

C20-C19 1,408(3) C11-C12-C13 118,1(5)

C3-H3 0,930(5) C11-C12-H12 121,0(5)

C3-C4 1,363(8) C13-C12-H12 121,0(5)

C14-H14a 0,970(3) N3-C23-H23a 110,3(3)

C14-H14b 0,969(3) N3-C23-H23b 110,3(3)

C14-C15 1,502(3) N3-C23-C23 107,2(2)

C4-H4 0,931(5) H23a-C23-H23b 108,5(3)

C1-C6 1,388(4) H23a-C23-C23 110,3(3)

Anexos 148

Tabela A1 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o Ligante H4L1. (continuação)

C7-H7a 0,970(3) H23b-C23-C23 110,3(3)

C7-H7b 0,970(3) C17-C21-H21a 109,5(3)

C7-C6 1,507(4) C17-C21-H21b 109,5(3)

C15-C16 1,383(4) C17-C21-H21C 109,5(3)

C9-C10 1,366(5) C17-C21-H21d 109,5(3)

O2-H2a 0,820(2) C17-C21-H21e 109,4(3)

N3-C22 1,270(4) C17-C21-H21f 109,5(3)

N3-C23 1,484(4) H21a-C21-H21b 109,5(3)

C16-H16 0,930(3) H21a-C21-H21C 109,4(3)

C16-C17 1,390(3) H21a-C21-H21d 141,0(4)

C17-C18 1,371(4) H21a-C21-H21e 56,2(2)

C17-C21 1,514(4) H21a-C21-H21f 56,3(2)

C19-C22 1,448(4) H21b-C21-H21C 109,5(3)

C19-C18 1,390(4) H21b-C21-H21d 56,3(2)

C10-H10 0,931(4) H21b-C21-H21e 141,1(4)

C10-C11 1,373(5) H21b-C21-H21f 56,3(2)

C22-H22 0,930(3) H21C-C21-H21d 56,2(2)

C18-H18 0,930(2) H21C-C21-H21e 56,3(2)

C11-H11 0,930(4) H21C-C21-H21f 141,0(4)

C11-C12 1,362(7) H21d-C21-H21e 109,4(3)

C13-H13 0,929(4) H21d-C21-H21f 109,5(3)

Anexos 149

A.1.2

Complexo 1

Tabela A2 – Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 1

Cu1-Cl1 2,323(2) Cl1-Cu1-O2 85,4(1)

Cu1-O2 1,886(4) Cl1-Cu1-N1 98,2(1)

Cu1-N1 1,973(4) Cl1-Cu1-N2 172,1(1)

Cu1-N2 2,052(5) Cl1-Cu1-O1 85,9(1)

Cu1-O1 2,555(4) Cl1-Cu1-Cl1 95,77(6)

Cu1-Cl1 2,889(2) O2-Cu1-N1 176,1(2)

Cl1-Cu1 2,889(2) O2-Cu1-N2 91,7(2)

O2-C20 1,312(7) O2-Cu1-O1 96,7(2)

N1-C1 1,334(9) O2-Cu1-Cl1 89,3(1)

N1-C5 1,344(9) N1-Cu1-N2 85,0(2)

N2-C14 1,488(7) N1-Cu1-O1 85,1(2)

N2-C6 1,489(8) N1-Cu1-Cl1 88,8(1)

N2-C7 1,496(8) N2-Cu1-O1 87,2(2)

O1-C13 1,386(8) N2-Cu1-Cl1 91,5(1)

N3-H3 0,86 O1-Cu1-Cl1 173,9(1)

N3-C21 1,310(9) Cu1-Cl1-Cu1 84,23(6)

N3-C22 1,45(1) Cu1-O2-C20 132,0(4)

C20-C19 1,415(8) Cu1-N1-C1 127,1(4)

C20-C15 1,381(8) Cu1-N1-C5 113,9(4)

C19-C21 1,40(1) C1-N1-C5 118,7(5)

C19-C18 1,42(1) Cu1-N2-C14 109,7(3)

C15-C14 1,517(8) Cu1-N2-C6 104,6(4)

C15-C16 1,368(9) Cu1-N2-C7 113,4(4)

C21-H21 0,929 C14-N2-C6 108,2(5)

C1-H1 0,931 C14-N2-C7 110,5(5)

C1-C2 1,37(1) C6-N2-C7 110,2(5)

C8-C7 1,49(1) Cu1-O1-C13 108,7(3)

C8-C9 1,35(1) H3-N3-C21 117,6

C8-C13 1,38(1) H3-N3-C22 117,4

C14-H14A 0,97 C21-N3-C22 125,1(6)

Anexos 150

Tabela A2 – Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 1. (continuação)

C14-H14B 0,971 O2-C20-C19 116,8(5)

C16-H16 0,93 O2-C20-C15 123,3(5)

C16-C17 1,40(1) C19-C20-C15 119,9(6)

C5-C6 1,51(1) C20-C19-C21 121,9(6)

C5-C4 1,372(9) C20-C19-C18 118,7(6)

C18-H18 0,93 C21-C19-C18 119,4(6)

C18-C17 1,37(1) C20-C15-C14 119,9(5)

C6-H6A 0,97 C20-C15-C16 119,1(6)

C6-H6B 0,972 C14-C15-C16 120,6(6)

C4-H4 0,93 N3-C21-C19 124,6(6)

C4-C3 1,39(1) N3-C21-H21 117,8

C17-C23 1,52(1) C19-C21-H21 117,6

C7-H7A 0,97 N1-C1-H1 118,8

C7-H7B 0,971 N1-C1-C2 122,4(7)

C22-H22A 0,969 H1-C1-C2 118,8

C22-H22B 0,971 C7-C8-C9 120,6(7)

C22-C22 1,48(1) C7-C8-C13 121,3(6)

C3-H3A 0,931 C9-C8-C13 118,1(7)

C3-C2 1,36(1) N2-C14-C15 115,1(5)

C9-H9 0,93 N2-C14-H14A 108,6

C9-C10 1,39(1) N2-C14-H14B 108,5

C13-C12 1,39(1) C15-C14-H14A 108,5

C2-H2 0,931 C15-C14-H14B 108,4

C12-H12 0,93 H14A-C14-H14B 107,5

C12-C11 1,35(1) C15-C16-H16 118,4

C10-H10 0,93 C15-C16-C17 123,4(7)

C10-C11 1,37(2) H16-C16-C17 118,2

C11-H11 0,93 N1-C5-C6 115,0(5)

C23-H23A 0,96 N1-C5-C4 122,2(6)

C23-H23B 0,96 C6-C5-C4 122,7(6)

C23-H23C 0,96 C19-C18-H18 119,2

O2-C20 1,312(7) C19-C18-C17 121,5(7)

O2-Cu1 1,886(4) H18-C18-C17 119,3

Anexos 151

Tabela A2 – Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 1. (continuação)

N1-C1 1,334(9) N2-C6-C5 112,1(5)

N1-C5 1,344(9) N2-C6-H6A 109,2

N1-Cu1 1,973(4) N2-C6-H6B 109,2

N2-C14 1,488(7) C5-C6-H6A 109,2

N2-C6 1,489(8) C5-C6-H6B 109,2

N2-C7 1,496(8) H6A-C6-H6B 107,7

N2-Cu1 2,052(5) C5-C4-H4 121,1

O1-C13 1,386(8) C5-C4-C3 117,8(8)

O1-Cu1 2,555(4) H4-C4-C3 121,1

N3-H3 0,86 C16-C17-C18 117,4(7)

N3-C21 1,310(9) C16-C17-C23 122,2(8)

N3-C22 1,45(1) C18-C17-C23 120,5(8)

C20-C19 1,415(8) N2-C7-C8 114,8(5)

C20-C15 1,381(8) N2-C7-H7A 108,6

C19-C21 1,40(1) N2-C7-H7B 108,5

C19-C18 1,42(1) C8-C7-H7A 108,7

C15-C14 1,517(8) C8-C7-H7B 108,5

C15-C16 1,368(9) H7A-C7-H7B 107,5

C21-H21 0,929 N3-C22-H22A 109,6

C1-H1 0,931 N3-C22-H22B 109,6

C1-C2 1,37(1) N3-C22-C22 110,3(6)

C8-C7 1,49(1) H22A-C22-H22B 108,1

C8-C9 1,35(1) H22A-C22-C22 109,6

C8-C13 1,38(1) H22B-C22-C22 109,5

C14-H14A 0,97 C4-C3-H3A 120

C14-H14B 0,971 C4-C3-C2 120,1(9)

C16-H16 0,93 H3A-C3-C2 120

C16-C17 1,40(1) C8-C9-H9 119,3

C5-C6 1,51(1) C8-C9-C10 121,6(8)

C5-C4 1,372(9) H9-C9-C10 119,1

C18-H18 0,93 O1-C13-C8 118,5(6)

C18-C17 1,37(1) O1-C13-C12 119,9(6)

C6-H6A 0,97 C8-C13-C12 121,5(7)

Anexos 152

Tabela A2 – Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 1. (continuação)

C6-H6B 0,972 C1-C2-C3 118,8(8)

C4-H4 0,93 C1-C2-H2 120,6

C4-C3 1,39(1) C3-C2-H2 120,6

C17-C23 1,52(1) C13-C12-H12 120,7

C7-H7A 0,97 C13-C12-C11 118,5(8)

C7-H7B 0,971 H12-C12-C11 120,8

C22-H22A 0,969 C9-C10-H10 121

C22-H22B 0,971 C9-C10-C11 118(1)

C3-H3A 0,931 H10-C10-C11 121

C3-C2 1,36(1) C12-C11-C10 122(1)

C9-H9 0,93 C12-C11-H11 119

C9-C10 1,39(1) C10-C11-H11 119

C13-C12 1,39(1) C17-C23-H23A 109,5

C2-H2 0,931 C17-C23-H23B 109,5

C12-H12 0,93 C17-C23-H23C 109,5

C12-C11 1,35(1) H23A-C23-H23B 109

C10-H10 0,93 H23A-C23-H23C 110

C10-C11 1,37(2) H23B-C23-H23C 109

C11-H11 0,93 C20-O2-Cu1 132,0(4)

C23-H23A 0,96 C1-N1-C5 118,7(5)

C23-H23B 0,96 C1-N1-Cu1 127,1(4)

C23-H23C 0,96 C5-N1-Cu1 113,9(4)

Cu1-Cl1 2,323(2) C14-N2-C6 108,2(5)

Cu1-Cl1 2,889(2) C14-N2-C7 110,5(5)

Cl1-Cu1 2,889(2) C14-N2-Cu1 109,7(3)

Cu1-Cl1 2,323(2) C6-N2-C7 110,2(5)

Cu1-Cl1 2,323(2) C6-N2-Cu1 104,6(4)

O4W-H4WA 0,849 C7-N2-Cu1 113,4(4)

O4W-H4WB 0,8509 C13-O1-Cu1 108,7(3)

O3W-H3WA 0,85 H3-N3-C21 117,6

O3W-H3WB 0,85 H3-N3-C22 117,4

O1W-H1WA 0,85 C21-N3-C22 125,1(6)

O1W-H1WB 0,85 O2-C20-C19 116,8(5)

Anexos 153

Tabela A2 – Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 1. (continuação)

O2W-H2WA 0,851 O2-C20-C15 123,3(5)

O2W-H2WB 0,85 C19-C20-C15 119,9(6)

O5W-H5WA 0,849 C20-C19-C21 121,9(6)

O5W-H5WB 0,85 C20-C19-C18 118,7(6)

C21-C19-C18 119,4(6)

C20-C15-C14 119,9(5)

C20-C15-C16 119,1(6)

C14-C15-C16 120,6(6)

N3-C21-C19 124,6(6)

N3-C21-H21 117,8

C19-C21-H21 117,6

N1-C1-H1 118,8

N1-C1-C2 122,4(7)

H1-C1-C2 118,8

C7-C8-C9 120,6(7)

C7-C8-C13 121,3(6)

C9-C8-C13 118,1(7)

N2-C14-C15 115,1(5)

N2-C14-H14A 108,6

N2-C14-H14B 108,5

C15-C14-H14A 108,5

C15-C14-H14B 108,4

H14A-C14-H14B 107,5

C15-C16-H16 118,4

C15-C16-C17 123,4(7)

H16-C16-C17 118,2

N1-C5-C6 115,0(5)

N1-C5-C4 122,2(6)

C6-C5-C4 122,7(6)

C19-C18-H18 119,2

C19-C18-C17 121,5(7)

H18-C18-C17 119,3

N2-C6-C5 112,1(5)

Anexos 154

Tabela A2 – Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 1. (continuação)

N2-C6-H6A 109,2

N2-C6-H6B 109,2

C5-C6-H6A 109,2

C5-C6-H6B 109,2

H6A-C6-H6B 107,7

C5-C4-H4 121,1

C5-C4-C3 117,8(8)

H4-C4-C3 121,1

C16-C17-C18 117,4(7)

C16-C17-C23 122,2(8)

C18-C17-C23 120,5(8)

N2-C7-C8 114,8(5)

N2-C7-H7A 108,6

N2-C7-H7B 108,5

C8-C7-H7A 108,7

C8-C7-H7B 108,5

H7A-C7-H7B 107,5

C22-C22-N3 110,3(6)

C22-C22-H22A 109,6

C22-C22-H22B 109,5

N3-C22-H22A 109,6

N3-C22-H22B 109,6

H22A-C22-H22B 108,1

C4-C3-H3A 120

C4-C3-C2 120,1(9)

H3A-C3-C2 120

C8-C9-H9 119,3

C8-C9-C10 121,6(8)

H9-C9-C10 119,1

O1-C13-C8 118,5(6)

O1-C13-C12 119,9(6)

C8-C13-C12 121,5(7)

C1-C2-C3 118,8(8)

Anexos 155

Tabela A2 – Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 1. (continuação)

C1-C2-H2 120,6

C3-C2-H2 120,6

C13-C12-H12 120,7

C13-C12-C11 118,5(8)

H12-C12-C11 120,8

C9-C10-H10 121

C9-C10-C11 118(1)

H10-C10-C11 121

C12-C11-C10 122(1)

C12-C11-H11 119

C10-C11-H11 119

C17-C23-H23A 109,5

C17-C23-H23B 109,5

C17-C23-H23C 109,5

H23A-C23-H23B 109

H23A-C23-H23C 110

H23B-C23-H23C 109

O2-Cu1-N1 176,1(2)

O2-Cu1-N2 91,7(2)

O2-Cu1-O1 96,7(2)

O2-Cu1-Cl1 85,4(1)

O2-Cu1-Cl1 89,3(1)

N1-Cu1-N2 85,0(2)

N1-Cu1-O1 85,1(2)

N1-Cu1-Cl1 98,2(1)

N1-Cu1-Cl1 88,8(1)

N2-Cu1-O1 87,2(2)

N2-Cu1-Cl1 172,1(1)

N2-Cu1-Cl1 91,5(1)

O1-Cu1-Cl1 85,9(1)

O1-Cu1-Cl1 173,9(1)

Cl1-Cu1-Cl1 95,77(6)

Cu1-Cl1-Cu1 84,23(6)

Anexos 156

Tabela A2 – Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 1. (continuação)

Cl1-Cu1-Cl1 95,77(6)

Cl1-Cu1-Cl1 95,77(6)

Cu1-Cl1-Cu1 84,23(6)

Cu1-Cl1-Cu1 84,23(6)

H4WA-O4W-

H4WB 109,36

H3WA-O3W-

H3WB 109,5

H1WA-O1W-

H1WB 109,4

H2WA-O2W-

H2WB 109,6

H5WA-O5W-

H5WB 109,6

Anexos 157

A.1.3

Complexo 3

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3

O1W-H1Wa 0,8499

H1WA-O1W-

H1WB 109.44

O1W-H1Wb 0,85 O1-Cu1-O2 78.5(2)

Cu1-O1 2,1629(1) O1-Cu1-O4 101.3(2)

Cu1-O2 1,9415(1) O1-Cu1-N1 110.3(2)

Cu1-O4 1,9657(1) O1-Cu1-N2 93.7(2)

Cu1-N1 2,0049(1) O2-Cu1-O4 96.8(2)

Cu1-N2 2,0493(1) O2-Cu1-N1 93.6(2)

Cu2-O1 1,9541(1) O2-Cu1-N2 169.6(2)

Cu2-O2 2,1267(1) O4-Cu1-N1 148.1(2)

Cu2-O3 1,9922(1) O4-Cu1-N2 91.5(2)

Cu2-N5 2,0208(1) N1-Cu1-N2 82.5(2)

Cu2-N6 1,9873(1) O1-Cu2-O2 79.1(2)

Cu3-O3 1,8398(1) O1-Cu2-O3 94.9(2)

Cu3-O4 1,9117(1) O1-Cu2-N5 171.5(2)

Cu3-N3 1,8774(1) O1-Cu2-N6 94.3(2)

Cu3-N4 1,8278(1) O2-Cu2-O3 99.7(2)

O1-C1 1,3294(1) O2-Cu2-N5 95.5(2)

O2-C46 1,3576(1) O2-Cu2-N6 114.8(2)

O3-H3 0,84 O3-Cu2-N5 92.5(2)

O3-C31 1,3483(1) O3-Cu2-N6 145.4(2)

O4-H4 0,84 N5-Cu2-N6 81.9(2)

O4-C20 1,3448(1) O3-Cu3-O4 112.5(4)

N1-C9 1,3664(1) O3-Cu3-N3 135.3(4)

N1-C13 1,3420(1) O3-Cu3-N4 90.2(4)

N2-C7 1,5038(1) O4-Cu3-N3 86.7(3)

N2-C8 1,4820(1) O4-Cu3-N4 128.2(4)

N2-C14 1,4876(1) N3-Cu3-N4 109.5(4)

N3-H3a 1,0000(1) Cu1-O1-Cu2 97.9(2)

N3-C22 1,4885(1) Cu1-O1-C1 121.0(4)

N3-C23 1,4915(1) Cu2-O1-C1 127.0(4)

Anexos 158

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3. (continuação)

N4-H4a 1,0000(1) Cu1-O2-Cu2 99.5(2)

N4-C24 1,4953(1) Cu1-O2-C46 127.9(4)

N4-C25 1,4831(1) Cu2-O2-C46 122.1(3)

N5-C33 1,4966(1) Cu2-O3-Cu3 124.4(3)

N5-C34 1,4782(1) Cu2-O3-C31 117.3(3)

N5-C40 1,5058(1) Cu3-O3-C31 117.1(4)

N6-C35 1,3385(1) Cu1-O4-Cu3 122.0(3)

N6-C391 1,4164(1) Cu1-O4-C20 116.9(4)

N6-C392 13.557 Cu3-O4-C20 120.8(4)

C1-C2 1,3949(1) Cu1-N1-C9 113.8(4)

C1-C6 1,4058(1) Cu1-N1-C13 126.6(4)

C2-H2 0,9500(1) C9-N1-C13 119.4(5)

C2-C3 1,3926(1) Cu1-N2-C7 107.6(3)

C3-H3b 0,95 Cu1-N2-C8 105.6(3)

C3-C4 1,3897(1) Cu1-N2-C14 115.2(3)

C4-H4b 0,95 C7-N2-C8 108.6(4)

C4-C5 1,3904(1) C7-N2-C14 109.3(4)

C5-H5 0,9500(1) C8-N2-C14 110.2(4)

C5-C6 1,3725(1) Cu3-N3-H3A 107.8

C7-H7a 0,9900(1) Cu3-N3-C22 129.6(5)

C7-H7b 0,99 Cu3-N3-C23 88.0(4)

C7-C6 1,5099(1) H3A-N3-C22 107.8

C8-H8a 0,99 H3A-N3-C23 107.7

C8-H8b 0,99 C22-N3-C23 113.3(5)

C8-C9 1,4815(1) Cu3-N4-H4A 109.1

C9-C10 1,3832(1) Cu3-N4-C24 88.3(4)

C10-H10 0,9500(1) Cu3-N4-C25 127.2(5)

C10-C11 1,3919(1) H4A-N4-C24 109.2

C11-H11 0,9500(1) H4A-N4-C25 109.1

C11-C12 1,3686(1) C24-N4-C25 111.6(5)

C12-H12 0,95 Cu2-N5-C33 115.1(4)

C12-C13 1,3925(1) Cu2-N5-C34 107.4(4)

C13-H13 0,9500(1) Cu2-N5-C40 107.2(4)

Anexos 159

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3. (continuação)

C14-H14a 0,9900(1) C33-N5-C34 109.5(5)

C14-H14b 0,9900(1) C33-N5-C40 108.1(5)

C14-C15 1,5007(1) C34-N5-C40 109.5(5)

C15-C16 1,3920(1) Cu2-N6-C35 115.1(5)

C15-C20 1,4100(1) Cu2-N6-C391 122.4(8)

C16-H16 0,95 C35-N6-C391 121.1(9)

C16-C17 13.785 O1-C1-C2 122.2(5)

C17-C18 1,3941(1) O1-C1-C6 119.2(5)

C17-C21 1,5101(1) C2-C1-C6 118.6(5)

C18-H18 0,95 C1-C2-H2 119.7

C18-C19 1,3929(1) C1-C2-C3 120.6(5)

C19-C20 14.123 H2-C2-C3 119.7

C19-C22 1,4967(1) C2-C3-H3B 119.6

C21-H21a 0,98 C2-C3-C4 120.8(6)

C21-H21b 0,9800(1) H3B-C3-C4 119.7

C21-H21C 0,98 C3-C4-H4B 121.0

C22-H22a 0,99 C3-C4-C5 118.0(6)

C22-H22b 0,99 H4B-C4-C5 121.0

C23-H23a 0,99 C4-C5-H5 118.8

C23-H23b 0,9900(1) C4-C5-C6 122.3(6)

C23-C24 1,4941(1) H5-C5-C6 118.9

C24-H24a 0,9900(1) N2-C7-H7A 108.6

C24-H24b 0,9900(1) N2-C7-H7B 108.5

C25-H25a 0,9900(1) N2-C7-C6 115.0(5)

C25-H25b 0,99 H7A-C7-H7B 107.5

C25-C26 1,4932(1) H7A-C7-C6 108.6

C26-C27 1,4029(1) H7B-C7-C6 108.5

C26-C31 1,4042(1) C1-C6-C5 119.7(5)

C27-H27 0,95 C1-C6-C7 120.1(5)

C27-C28 1,3827(1) C5-C6-C7 120.0(5)

C28-C29 1,3956(1) N2-C8-H8A 109.4

C28-C32 1,5181(1) N2-C8-H8B 109.4

C29-H29 0,9500(1) N2-C8-C9 111.0(5)

Anexos 160

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3. (continuação)

C29-C30 1,3968(1) H8A-C8-H8B 108.1

C30-C31 1,4035(1) H8A-C8-C9 109.4

C30-C33 1,5079(1) H8B-C8-C9 109.4

C32-H32a 0,98 N1-C9-C8 114.3(5)

C32-H32b 0,98 N1-C9-C10 120.9(6)

C32-H32C 0,98 C8-C9-C10 124.8(6)

C33-H33a 0,9900(1) C9-C10-H10 120.6

C33-H33b 0,99 C9-C10-C11 118.8(7)

C34-H34a 0,99 H10-C10-C11 120.6

C34-H34b 0,9900(1) C10-C11-H11 119.8

C34-C35 1,4972(1) C10-C11-C12 120.5(7)

C35-C361 1,4243(1) H11-C11-C12 119.7

C35-C362 1,4083(1) C11-C12-H12 120.9

C361-H361 0,9500(1) C11-C12-C13 118.2(7)

C361-C371 1,3563(1) H12-C12-C13 120.9

C361-C362 0,6491 N1-C13-C12 122.1(6)

C361-H362 1,3415(1) N1-C13-H13 119.0

C361-C372 1,4205(1) C12-C13-H13 118.9

H361-C362 1,0886(1) N2-C14-H14A 109.0

C371-H371 0,95 N2-C14-H14B 108.9

C371-C381 1,3536(1) N2-C14-C15 112.9(5)

C371-C372 0,8506 H14A-C14-H14B 107.8

C371-H372 1,3295(1) H14A-C14-C15 109.1

H371-C372 1,2927(1) H14B-C14-C15 109.0

C381-H381 0,95 C14-C15-C16 122.5(5)

C381-C391 1,4033(1) C14-C15-C20 118.3(5)

C381-C382 0,9063 C16-C15-C20 119.0(5)

C381-C392 1,4764(1) C15-C16-H16 118.6

H381-C382 1,3580(1) C15-C16-C17 122.9(6)

C391-H391 0,9500(1) H16-C16-C17 118.5

C391-C392 0,718 C16-C17-C18 117.1(6)

C391-H392 1,1223(1) C16-C17-C21 121.3(6)

C362-H362 0,9500(1) C18-C17-C21 121.6(6)

Anexos 161

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3. (continuação)

C362-C372 1,4102(1) C17-C18-H18 118.6

C372-H372 0,95 C17-C18-C19 122.8(6)

C372-C382 1,3886(1) H18-C18-C19 118.6

C382-H382 0,95 C18-C19-C20 118.7(6)

C382-C392 1,3936(1) C18-C19-C22 122.4(6)

C392-H392 0,9500(1) C20-C19-C22 118.9(6)

C40-H40a 0,99 O4-C20-C15 120.2(5)

C40-H40b 0,9900(1) O4-C20-C19 120.4(5)

C40-C41 1,5023(1) C15-C20-C19 119.2(5)

C41-C42 1,3987(1) C17-C21-H21A 109.4

C41-C46 1,4077(1) C17-C21-H21B 109.5

C42-H42 0,9500(1) C17-C21-H21C 109.5

C42-C43 1,3689(1) H21A-C21-H21B 109.5

C43-H43 0,95 H21A-C21-H21C 109.5

C43-C44 1,3942(1) H21B-C21-H21C 109.5

C44-H44 0,95 N3-C22-C19 109.2(5)

C44-C45 1,3909(1) N3-C22-H22A 109.9

C45-H45 0,9500(1) N3-C22-H22B 109.9

C45-C46 1,3816(1) C19-C22-H22A 109.8

Cl1-O13 1,4162(1) C19-C22-H22B 109.9

Cl1-O14 1,4223(1) H22A-C22-H22B 108.3

Cl1-O11 1,4195(1) N3-C23-H23A 109.2

Cl1-O12 1,3968(1) N3-C23-H23B 109.2

Cl22-O25 1,3962(1) N3-C23-C24 112.2(5)

Cl22-O26 1,3991(1) H23A-C23-H23B 107.8

Cl22-O27 1,3955(1) H23A-C23-C24 109.2

Cl22-O28 1,4395(1) H23B-C23-C24 109.2

Cl22-O21 1,5977(1) N4-C24-C23 111.4(5)

Cl22-O22 1,2350(1) N4-C24-H24A 109.3

Cl22-O23 1,6497(1) N4-C24-H24B 109.4

Cl22-O24 1,2659(1) C23-C24-H24A 109.4

O25-CL21 1,6476(1) C23-C24-H24B 109.3

O25-O22 1,5816(1) H24A-C24-H24B 107.9

Anexos 162

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3. (continuação)

O25-O24 1,7154(1) N4-C25-H25A 109.9

O26-CL21 1,4768(1) N4-C25-H25B 109.9

O26-O23 1,7803(1) N4-C25-C26 109.4(5)

O26-O24 0,9691(1) H25A-C25-H25B 108.2

O27-CL21 1,3843(1) H25A-C25-C26 109.8

O27-O22 0,8609 H25B-C25-C26 109.6

O27-O23 1,7071(1) C25-C26-C27 121.9(6)

O28-CL21 1,1995(1) C25-C26-C31 119.6(6)

O28-O21 0,7121 C27-C26-C31 118.5(6)

Cl21-O21 1,4233(1) C26-C27-H27 118.8

Cl21-O22 1,3936(1) C26-C27-C28 122.5(7)

Cl21-O23 1,4213(1) H27-C27-C28 118.8

Cl21-O24 13.928 C27-C28-C29 118.0(7)

O1D-C1D 1,2273(1) C27-C28-C32 120.6(7)

C1D-H1D 0,95 C29-C28-C32 121.4(6)

C1D-N1D 1,2978(1) C28-C29-H29 119.4

N1D-C3D 1,4458(1) C28-C29-C30 121.3(6)

N1D-C2D 1,4353(1) H29-C29-C30 119.4

C3D-H3Da 0,98 C29-C30-C31 119.7(6)

C3D-H3Db 0,9800(1) C29-C30-C33 121.5(5)

C3D-H3DC 0,98 C31-C30-C33 118.5(5)

C2D-H2Da 0,98 O3-C31-C26 119.5(5)

C2D-H2Db 0,9800(1) O3-C31-C30 120.6(5)

C2D-H2DC 0,98 C26-C31-C30 119.7(5)

C28-C32-H32A 109.4

C28-C32-H32B 109.5

C28-C32-H32C 109.5

H32A-C32-H32B 109.5

H32A-C32-H32C 109.4

H32B-C32-H32C 109.5

N5-C33-C30 112.6(5)

N5-C33-H33A 109.1

N5-C33-H33B 109.1

Anexos 163

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3. (continuação)

C30-C33-H33A 109.1

C30-C33-H33B 108.9

H33A-C33-H33B 107.9

N5-C34-H34A 109.5

N5-C34-H34B 109.5

N5-C34-C35 110.5(6)

H34A-C34-H34B 108.1

H34A-C34-C35 109.6

H34B-C34-C35 109.6

N6-C35-C34 114.6(7)

N6-C35-C361 119(1)

C34-C35-C361 125.0(9)

C35-C361-H361 120

C35-C361-C371 120(2)

H361-C361-C371 120

C361-C371-H371 120

C361-C371-C381 119(2)

H371-C371-C381 120

C371-C381-H381 119

C371-C381-C391 122(2)

H381-C381-C391 119

N6-C391-C381 116(1)

N6-C391-H391 122

C381-C391-H391 122

N5-C40-H40A 108.4

N5-C40-H40B 108.4

N5-C40-C41 115.5(5)

H40A-C40-H40B 107.5

H40A-C40-C41 108.4

H40B-C40-C41 108.4

C40-C41-C42 119.8(5)

C40-C41-C46 122.1(5)

C42-C41-C46 118.0(5)

Anexos 164

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3. (continuação)

C41-C42-H42 119.2

C41-C42-C43 121.6(6)

H42-C42-C43 119.2

C42-C43-H43 120.2

C42-C43-C44 119.8(6)

H43-C43-C44 120.0

C43-C44-H44 120.1

C43-C44-C45 119.7(6)

H44-C44-C45 120.2

C44-C45-H45 119.8

C44-C45-C46 120.3(6)

H45-C45-C46 119.9

O2-C46-C41 118.2(5)

O2-C46-C45 121.5(5)

C41-C46-C45 120.4(5)

O13-Cl1-O14 110.0(3)

O13-Cl1-O11 110.5(4)

O13-Cl1-O12 109.5(4)

O14-Cl1-O11 107.8(4)

O14-Cl1-O12 110.6(4)

O11-Cl1-O12 108.4(4)

O1D-C1D-H1D 117.7

O1D-C1D-N1D 124.6(8)

H1D-C1D-N1D 117.7

C1D-N1D-C3D 121.9(8)

C1D-N1D-C2D 120.3(8)

C3D-N1D-C2D 117.6(8)

N1D-C3D-H3DA 109.6

N1D-C3D-H3DB 109.5

N1D-C3D-H3DC 109.5

H3DA-C3D-H3DB 109.4

H3DA-C3D-H3DC 109.4

H3DB-C3D-H3DC 109.4

Anexos 165

Tabela A3 - Comprimentos (Å, esquerda) e ângulos (˚, direita) de ligação

para o complexo 3. (continuação)

N1D-C2D-H2DA 109

N1D-C2D-H2DB 109

N1D-C2D-H2DC 109

H2DA-C2D-H2DB 110

H2DA-C2D-H2DC 109

H2DB-C2D-H2DC 109

Anexos 166

A.2

RMN

A.2.1

HBPA

Figura A1 – Espectro de RMN 1H HBPA em DMSO-d6 a temperatura

ambiente entre (6,6 – 8,8) ppm.

Figura A2 – Espectro de RMN 1H HBPA em DMSO-d6 a temperatura

ambiente entre (1,0 – 6,0) ppm.

Anexos 167

A.2.2

2,5-Bis(clorometil)-1,4-dimetoxibenzeno

Figura A3- Espectro de RMN 1H para o 2,5-Bis(clorometil)-1,4-

dimetoxibenzeno em DMSO-d6 a temperatura ambiente.

Anexos 168

A.2.3

Hbpamff

Figura A4- Espectro de RMN 1H para o Hbpamff em DMSO-d6 a temperatura

ambiente entre (6,5-10,2) ppm.

Figura A5- Espectro de RMN 1H para o Hbpamff em DMSO-d6 a temperatura

ambiente entre (2,0-6,0) ppm.

Anexos 169

A.3

Espectros de infravermelho

A.3.1

HBPA / Hbpamff / 2,5-Bis(clorometil)-1,4-dimetoxibenzeno

Figura A6- Espectro de infravermelho do HBPA na região (4000-450) cm-1

em pastilha de KBr.

Figura A7- Espectro de infravermelho do Hbpamff na região (4000-450) cm-1

em pastilha de KBr.

Anexos 170

Figura A8- Espectro de infravermelho do 2,5-Bis(clorometil)-1,4-

dimetoxibenzeno na região (4000-450) cm-1 em pastilha de KBr.

A.3.2

Segunda derivada dos espectros dos ligantes

Figura A9 - Espectro experimental do ligante H4L1 e segunda derivada na

região (3500-2500) cm-1.

Anexos 171

Figura A10 - Espectro experimental do ligante H4L1 e segunda derivada na

região (1750-1100) cm-1.

Figura A11 - Espectro experimental do ligante H4L2 e segunda derivada na

região (1650-1400) cm-1.

Anexos 172

Figura A12 - Espectro experimental do ligante H2L3 e segunda derivada na

região (3200-2600) cm-1.

Figura A13 - Espectro experimental do ligante H2L3 e segunda derivada na

região (1700 - 1400) cm-1.

Anexos 173

A.3.3

Espectros de infravermelho dos complexos da região (4000-450) cm-1

Figura A14 - Espectro de infravermelho do complexo 1 na região (4000-450)

cm-1 em pastilha de KBr.

Figura A15 - Espectro de infravermelho do Complexo 2 na região (4000-450)

cm-1 em pastilha de KBr.

Anexos 174

Figura A16 - Espectro de infravermelho do complexo 3 na região (4000-450)

cm-1 em pastilha de KBr.

Figura A17 - Espectro de infravermelho do complexo 4 na região (4000-450)

cm-1 em pastilha de KBr.

Anexos 175

A.3.4

Espectros de infravermelho dos complexos da região (700-30) cm-1

Figura A18 - Espectro de infravermelho do ligante H4L1 na região (700-30)

cm-1 em pastilha de polietileno.

Figura A19 - Espectro de infravermelho do ligante H4L2 na região (700-30)

cm-1 em pastilha de polietileno.

Anexos 176

Figura A20 - Espectro de infravermelho do ligante H4L3 na região (700-30)

cm-1 em pastilha de polietileno.

Anexos 177

A.4

Ressonância Paramagnética Eletrônica dos Complexos de Cobre

Figura A21 - RPE do Complexo 1 no estado sólido.

Figura A22 - RPE do Complexo 3 no estado sólido.

Anexos 178

Figura A23 - RPE do complexo 1 em solução à temperatura ambiente.

Figura A24 - RPE do complexo 3 em solução à temperatura ambiente.

Anexos 179

Figura A25 - RPE do complexo 1 em solução à N2 líquido.

Figura A26 - RPE do complexo 3 em solução à N2 líquido.

Anexos 180

Figura A27 - RPE do complexo 5 no estado sólido.

Figura A28 - RPE do complexo 5 à temperatura ambiente.

Anexos 181

Figura A29 - RPE do complexo 5 em N2 líquido.

Anexos 182

A.5

Publicação em periódico

Anexos 183

Anexos 184

Anexos 185

Anexos 186

Anexos 187

Anexos 188

Anexos 189

Anexos 190

Anexos 191

Anexos 192

Anexos 193

Anexos 194

Anexos 195

Anexos 196

Anexos 197

Anexos 198