Supplementary materials
Xinmiao Wang • Chunyan Ren • Wentao Zhang • Xiang Zhou • Yang Liu • Ping Liu* • Yaoyu Wang
* Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of
Education, Shaanxi Key Laboratory of Physico-Inorganic Chemistry, College of Chemistry &
Materials Science, Northwest University, Xi'an 710069, Shanxi Province, P. R. China
Table S1 Crystal and structure refine data for complexes 1 and 2
Complex
Empirical formula
Formula mass
Crystal system
Space group
a [Å]
b [Å]
c [Å]
α/(°)
β/(°)
γ/(°)
V[Å3]
Z
Dcalcd.[g·cm-3]
µ[mm-1]
F[000]
θ [º]
Reflections collected
Goodness-of-fit on F2
Final Ra indices [I > 2σ(I)]
1
C10H13CuN3O6
334.77
monoclinic
P21/c
7.3929(9)
18.801(2)
9.4109(1)
90.00
106.502(2)
90.00
1254.2(3)
4
1.773
1.772
684
2.17-25.10
6327
1.040
R1=0.0394
wR2=0.0838
2
C12H15CuN3O6
360.81
monoclinic
P21/c
7.165(2)
22.07(5)
10.934(2)
90.00
125.970(4)
90.00
1399(5)
4
1.713
1.595
740
2.48-24.65
6420
1.015
R1=0.0529
wR2=0.1589
[a]R 1= Σ(|Fo|–|Fc|)/Σ|Fo|; wR2 = [Σw(Fo2 – Fc2)2/Σw(Fo2) 2]1/2
Table S2 Selected Bond Lengths (Å) and Angles (o) for Complex 1 and 2
1
Cu(1)-O(1)
1.933(2)
Cu(1)-N(1)
2.027(3)
Cu(1)-N(2)
1.941(3)
Cu(1)-O(1W)
2.328(3)
Cu(1)-O(2)
1.966(2)
O(1)-Cu(1)-N(2)
169.81(1)
O(2)-Cu(1)-O(1W)
93.04(9)
O(1)-Cu(1)-O(2)
84.64(9)
N(1)-Cu(1)-O(1W)
100.14(1)
N(2)-Cu(1)-O(2)
98.19(1)
C(10)-O(2)-Cu(1)
112.8(2)
O(1)-Cu(1)-N(1)
93.46(1)
C(9)-O(1)-Cu(1)
113.0(2)
N(2)-Cu(1)-N(1)
81.55(1)
C(8)-N(1)-Cu(1)
128.3(2)
O(2)-Cu(1)-N(1)
166.77(1)
C(4)-N(1)-Cu(1)
113.3(2)
O(1)-Cu(1)-O(1W)
93.29(1)
C(1)-N(2)-Cu(1)
114.9(2)
N(2)-Cu(1)-O(1W)
96.27(1)
C(2)-N(2)-Cu(1)
136.9(2)
2
Cu(1)-O(1)
1.938(6)
Cu(1)-N(1)
2.030(7)
Cu(1)-N(2)
1.963(6)
Cu(1)-O(4)#1
2.186(7)
Cu(1)-O(5)
1.990(6)
O(4)-Cu(1)#2
2.186(7)
O(1)-Cu(1)-N(2)
92.7(2)
O(5)-Cu(1)-O(4)#1
94.74(2)
O(1)-Cu(1)-O(5)
93.0(2)
N(1)-Cu(1)-O(4)#1
87.3(2)
N(2)-Cu(1)-O(5)
163.7(2)
C(1)-N(1)-Cu(1)
128.7(5)
O(1)-Cu(1)-N(1)
172.20(2)
C(5)-N(1)-Cu(1)
114.0(4)
N(2)-Cu(1)-N(1)
80.7(2)
C(6)-N(2)-Cu(1)
115.8(4)
O(5)-Cu(1)-N(1)
92.3(2)
C(8)-N(2)-Cu(1)
136.3(5)
O(1)-Cu(1)-O(4)#1
98.0(2)
C(9)-O(1)-Cu(1)
112.6(4)
N(2)-Cu(1)-O(4)#1
99.6(2)
C(12)-O(4)-Cu(1)#2
141.5(5)
Symmetry transformations used to generate equivalent atoms: #1 x + 1, − y + 1/2, z + 1/2; #2 x − 1,
− y + 1/2, z − 1/2
Table S3 Hydrogen bond geometries in the crystal structure of 1
1
D−H···A
O(2W) –H(2W1)···O(3)#3
O(2W)−H(2W2)···O(2)#1
N(3)−H(3)···O(4)#1
N(3)−H(3)···O(3)#1
O(1W)−H(1W1)···O(4)#4
O(1W)−H(1W2)···O(2W)#3
O(1W)−H(1W2)···O(1)#4
C(2)−H(2B)···O(2)#2
C(5)−H(5)···O(4)#1
C(8)−H(8)···O(2W)#3
D−H
0.84
0.85
0.85
0.85
0.84
0.84
0.85
0.96
0.93
0.93
H···A
2.07
1.99
2.09
2.63
2.06
1.99
2.61
2.57
2.28
2.53
D···A(Å)
2.924(3)
2.834(3)
2.951(4)
3.142(4)
2.887(3)
2.835(3)
3.286(3)
3.416(2)
3.194(1)
3.288(5)
D−H···A(o)
174.1
171.5
171.0
118.5
162.7
170.8
136.6
145.8
164.7
137.9
Symmetry transformations used to generate equivalent atoms: #1 x, y, z; #2 − x, y + 1/2, − z + 1/2;
#3 – x, − y, − z; #4 x, − y − 1/2, z − 1/2
Table S4 Hydrogen bond geometries in the crystal structure of 2
2
D−H···A
N(3)−H(3A)···O(3)#2
N(3)−H(3A)···O(4)#2
O(5)-H(5A)O(3)#4
O(5)-H(5B)O(6)
O(6)−H(6A)···O(1)#4
O(6)−H(6B)···O(2)#4
C(4)−H(4)···O(4)#3
D−H
0.82
0.82
0.82
0.86
0.86
0.85
0.93
H···A
2.57
2.32
1.80
1.93
2.33
1.97
2.42
D···A(Å)
3.058(1)
3.049(1)
2.605(8)
2.712(9)
2.889(8)
2.819(1)
3.213(4)
∠D−H···A(o)
164.2
139.1
168.1
169.0
179.4
179.0
142.0
Symmetry transformations used to generate equivalent atoms: #1 x, y, z; #2 − x, y + 1/2, − z + 1/2;
#3 – x, − y, − z; #4 x, − y − 1/2, z − 1/2
Fig. S1 (a) 1D B-type zigzag chain (b) 2D A-type layer formed by hydrogen bond interactions
(green dotted lines) and the hydrogen atoms are omitted for clarity
Fig. S2 3D supramolecular architecture of 2 via hydrogen bond interactions (green dotted lines)
and the hydrogen atoms are omitted for clarity