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Supplementary Data
DBSA catalyzed cyclotrimerization of acetophenones: An efficient synthesis of 1,3,5-triarylbenzenes under solvent-free conditions

Davinder Prasad, Amreeta Preetam, Mahendra Nath*
Department of Chemistry, University of Delhi, Delhi 110 007, India
*E-mail: mnath@chemistry.du.ac.in (M. Nath)






Figure 1.1H NMR spectrum of 2a

Figure 2. 13C NMR spectrum of 2a

Figure 3. 1H NMR spectrum of 2b

Figure 4. 13C NMR spectrum of 2b

Figure 5. 1H NMR spectrum of 2c

Figure 6. 13C NMR spectrum of 2c

Figure 7. 1H NMR spectrum of 2d

Figure 8. 13C NMR spectrum of 2d

Figure 9. 1H NMR spectrum of 2e




Figure 10. 13C NMR spectrum of 2e




Figure 11. 1H NMR spectrum of 2f

Figure 12. 13C NMR spectrum of 2f

Figure 13. 1H NMR spectrum of 2g

Figure 14. 13C NMR spectrum of 2g

Figure 15. 1H NMR spectrum of 2h

Figure 16. 1H NMR spectrum of 2i

Figure 17. 13C NMR spectrum of 2i

Figure 18. 1H NMR spectrum of 2j

Figure 19. 13C NMR spectrum of 2j

Figure 20. 1H NMR spectrum of 2k

Figure 21. 13C NMR spectrum of 2k


Figure 22. 1H NMR spectrum of 2l




Figure 23. 13C NMR spectrum of 2l




Figure 24. 1H NMR spectrum of 2m




Figure 25. 13C NMR spectrum of 2m



Figure 26. 1H NMR spectrum of 2n

Figure 27. 13C NMR spectrum of 2n



Table 1. Crystal data and structure refinement for compound 2a
Empirical formula 	C24 H18
Formula weight 	306.38
Temperature 	293(2) K
Wavelength 	0.71073 Å
Crystal system 	Orthorhombic
Space group 	P n 21 a
a 	7.6204(15) Å
b 	11.2653(17) Å
c 	19.772(5) Å
α	90°
β	90°
γ 	90°
Volume	1697.3(6) Å3
Z	4
Density (calculated)	1.199 Mg/m3
Absorption coefficient	0.068 mm-1
F(000)	648
Crystal size	0.22 x 0.19 x 0.18 mm3
Theta range for data collection	3.38 to 24.99°
Index ranges	-9 ≤ h ≤ 9, -13 ≤ k ≤ 8, -23 ≤ l ≤ 20
Reflections collected	4147
Independent reflections	2148 [R(int) = 0.0185]
Completeness to theta = 24.99°	99.8 % 
Absorption correction	Semi-empirical from equivalents
Max. and min. transmission	0.9879 and 0.9853
Refinement method	Full-matrix least-squares on F2
Data / restraints / parameters	2148 / 1 / 217
Goodness-of-fit on F2	1.000
Final R indices [I>2sigma(I)]a, b	R1 = 0.0397, wR2 = 0.0866
R indices (all data)	R1 = 0.0462, wR2 = 0.0909
Largest diff. peak and hole	0.094 and -0.156 e.Å-3
aR = ∑(║Fo│– │Fc║)/∑│Fo│; bRW = {∑[w(Fo2 ─ Fc2)2]/∑[w(Fo2)2]}1/2
 Figure 1. Structure of compound 2a
The intensity data for compound 2a was collected on an Oxford Xcalibur CCD diffractometer equipped with graphite monochromatic Mo-Ka radiation (λ = 0.71073 Ǻ) at 293(2) K [1]. A multi-scan correction was applied. The structure was solved by the direct methods using SIR-92 and refined by full-matrix least-squares refinement techniques on F2 using SHELXL97 [2]. The hydrogen atoms were placed into the calculated positions and included in the last cycles of the refinement. All calculations were done using Wingx software package [3].

1.	CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (2011).
2.	G. M. Sheldrick, Acta Cryst., 2008, A64, 112-122.
3.	L. J. Farrugia, WinGX Version 1.80.05, An integrated system of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data; Department of Chemistry, University of Glasgow (1997-2009).



5





DBSA catalyzed cyclotrimerization of acetophenones: An efficient synthesis of 1,3,5-triarylbenzenes under solvent-free conditions

Jon D. Silversides

Benjamin P. Burke

Stephen J. Archibald

S1
Supplementary Data
Rapid synthesis of cross-bridged cyclam chelators for copper(II) complex
formation
Jon D. Silversides, Benjamin P. Burke and Stephen J. Archibald*
CONTENTS:
1. Alternative view of the X-ray crystal structure of [Cu2Cl2] S2
2. Description of crystal packing S2-S4
3. Full tables of bond lengths and angles for X-ray crystal structures S5-S6
4. References S7
S2
5. Alternative view of the X-ray crystal structure of [Cu2Cl2]
2. Description of crystal packing
[Cu1NO3]NO3.CH3OH has a cationic macrocyclic unit with an unbound nitrate counter anion.
As the triclinic unit cell is centrosymmetric, there are two macrocyclic units and two nitrate
residues per unit cell. Planes of macrocyclic units lie parallel to the diagonal of (010) and (001),
see Figure S2. The cavities of the macrocycles in adjacent planes are oriented towards each
other. As a result, the aryl groups of adjacent molecular units lie at an angle to each other. This
reduces electrostatic repulsion between the two adjacent π-systems.[1] 
The two chloride counterions coordinated to the metal centre in [Cu2Cl2] result in the complex
being a neutral species with no unbound ions in the crystal lattice. The extra symmetry of the
molecule is reflected in the more symmetrical monoclinic unit cell. Planes of macrocyclic units
run parallel to all three faces of the unit cell, showing regular packing of the macrocycles. In
contrast to [Cu1NO3]NO3.CH3OH, the cavities of the macrocycles are not oriented towards each
other.  The coplanar aryl groups run parallel to (001), with the π-systems arranged above each 
other, see Figure S3.  The staggered nature of the aryl groups shows π-stacking between adjacent 
planes.[1] The distance between two adjacent aryl groups is approximately 3.6 Å, which is an
appropriate distance for π-stacking.[1, 2]  
Figure S1. View of [Cu2Cl2] showing the twist of Cl1-Cu1-Cl2 plane vs, N1-Cu1-N3 plane
S3
Figure S2. Unit cell of [Cu1NO3]NO3CH3OH, shown normal to (100). Unit cell outline shown
in green
S4
Figure S3. Unit cell of [Cu2Cl2], viewed normal to (010) (above) and (001). Unit cell outline
shown in green
S5
3. Full tables of bond lengths and angles for X-ray crystal structures
C(2)-N(2) 1.477(5) N(5)-O(2) 1.235(4) O(1)-Cu(1)-N(1) 168.55(11)
C(2)-C(1) 1.500(5) N(5)-O(3) 1.258(4) O(1)-Cu(1)-N(2) 88.40(11)
C(1)-N(1) 1.493(5) N(5)-O(1) 1.297(4) N(1)-Cu(1)-N(2) 85.19(12)
C(10)-N(1) 1.495(4) N(6)-O(6) 1.216(5) O(1)-Cu(1)-N(4) 93.42(11)
C(10)-C(9) 1.501(5) N(6)-O(4) 1.234(5) N(1)-Cu(1)-N(4) 93.21(12)
C(9)-C(8) 1.516(5) N(6)-O(5) 1.247(5) N(2)-Cu(1)-N(4) 177.83(12)
C(8)-N(4) 1.489(4) O(1)-Cu(1)-N(3) 102.99(11)
C(7)-N(4) 1.487(4) N(2)-C(2)-C(1) 109.0(3) N(1)-Cu(1)-N(3) 86.86(11)
C(7)-C(6) 1.510(5) N(1)-C(1)-C(2) 109.9(3) N(2)-Cu(1)-N(3) 93.18(11)
C(6)-N(3) 1.481(5) N(1)-C(10)-C(9) 116.0(3) N(4)-Cu(1)-N(3) 85.27(11)
C(5)-N(3) 1.481(4) C(10)-C(9)-C(8) 116.7(3) C(2)-N(2)-C(3) 111.7(3)
C(5)-C(4) 1.520(5) N(4)-C(8)-C(9) 115.5(3) C(2)-N(2)-C(13) 110.6(3)
C(4)-C(3) 1.513(5) N(4)-C(7)-C(6) 110.2(3) C(3)-N(2)-C(13) 108.6(3)
C(3)-N(2) 1.499(4) N(3)-C(6)-C(7) 111.6(3) C(2)-N(2)-Cu(1) 106.6(2)
C(11)-N(1) 1.503(4) N(3)-C(5)-C(4) 115.2(3) C(3)-N(2)-Cu(1) 111.2(2)
C(11)-C(12) 1.534(5) C(3)-C(4)-C(5) 118.1(3) C(13)-N(2)-Cu(1) 108.1(2)
C(12)-N(3) 1.473(5) N(2)-C(3)-C(4) 116.7(3) C(1)-N(1)-C(10) 107.8(3)
C(13)-N(2) 1.509(5) N(1)-C(11)-C(12) 114.7(3) C(1)-N(1)-C(11) 109.8(3)
C(13)-C(14) 1.509(5) N(3)-C(12)-C(11) 114.7(3) C(10)-N(1)-C(11) 110.7(3)
C(14)-C(15) 1.381(5) N(2)-C(13)-C(14) 117.9(3) C(1)-N(1)-Cu(1) 106.3(2)
C(14)-C(19) 1.387(5) C(15)-C(14)-C(19) 117.6(3) C(10)-N(1)-Cu(1) 113.0(2)
C(15)-C(16) 1.381(6) C(15)-C(14)-C(13) 121.4(3) C(11)-N(1)-Cu(1) 109.0(2)
C(16)-C(17) 1.389(6) C(19)-C(14)-C(13) 120.8(3) C(7)-N(4)-C(8) 111.6(3)
C(17)-C(18) 1.380(6) C(14)-C(15)-C(16) 121.3(3) C(7)-N(4)-C(21) 109.6(3)
C(17)-C(20) 1.506(6) C(15)-C(16)-C(17) 121.3(4) C(8)-N(4)-C(21) 107.0(3)
C(18)-C(19) 1.384(5) C(18)-C(17)-C(16) 117.3(4) C(7)-N(4)-Cu(1) 105.2(2)
C(21)-N(4) 1.509(4) C(18)-C(17)-C(20) 120.4(4) C(8)-N(4)-Cu(1) 112.3(2)
C(21)-C(22) 1.513(5) C(16)-C(17)-C(20) 122.3(4) C(21)-N(4)-Cu(1) 111.2(2)
C(22)-C(23) 1.383(5) C(17)-C(18)-C(19) 121.5(3) C(12)-N(3)-C(6) 112.2(3)
C(22)-C(27) 1.395(5) C(18)-C(19)-C(14) 121.0(3) C(12)-N(3)-C(5) 112.6(3)
C(23)-C(24) 1.380(5) N(4)-C(21)-C(22) 117.4(3) C(6)-N(3)-C(5) 109.4(3)
C(24)-C(25) 1.400(5) C(23)-C(22)-C(27) 117.4(3) C(12)-N(3)-Cu(1) 106.9(2)
C(25)-C(26) 1.395(5) C(23)-C(22)-C(21) 121.8(3) C(6)-N(3)-Cu(1) 102.77(19)
C(25)-C(28) 1.491(5) C(27)-C(22)-C(21) 120.4(3) C(5)-N(3)-Cu(1) 112.6(2)
C(26)-C(27) 1.374(5) C(24)-C(23)-C(22) 121.5(3) O(2)-N(5)-O(3) 124.6(3)
C(29)-O(7) 1.335(9) C(23)-C(24)-C(25) 121.3(3) O(2)-N(5)-O(1) 118.1(3)
Cu(1)-O(1) 1.989(3) C(26)-C(25)-C(24) 116.8(3) O(3)-N(5)-O(1) 117.3(3)
Cu(1)-N(1) 2.038(3) C(26)-C(25)-C(28) 121.7(3) O(6)-N(6)-O(4) 118.3(4)
Cu(1)-N(2) 2.096(3) C(24)-C(25)-C(28) 121.5(3) O(6)-N(6)-O(5) 121.9(5)
Cu(1)-N(4) 2.131(3) C(27)-C(26)-C(25) 121.5(3) O(4)-N(6)-O(5) 119.7(3)
Cu(1)-N(3) 2.154(3) C(26)-C(27)-C(22) 121.4(3) N(5)-O(1)-Cu(1) 112.5(2)
Table S1. Bond lengths (Å) and angles (°) for [Cu1NO3]NO3.CH3OH
S6
C(1)-N(1) 1.502(11) Cu(1)-Cl(2) 2.302(2) C(11)-N(1)-C(10) 110.6(7)
C(1)-C(2) 1.546(14) Cu(1)-Cl(1) 2.322(2) C(11)-N(1)-C(1) 108.0(7)
C(2)-N(2) 1.459(12) C(10)-N(1)-C(1) 105.7(6)
C(3)-N(2) 1.507(11) N(1)-C(1)-C(2) 110.6(6) C(11)-N(1)-Cu(1) 112.4(5)
C(3)-C(4) 1.514(13) N(2)-C(2)-C(1) 112.6(8) C(10)-N(1)-Cu(1) 112.7(6)
C(4)-C(5) 1.487(13) N(2)-C(3)-C(4) 115.6(8) C(1)-N(1)-Cu(1) 107.0(5)
C(5)-N(3) 1.464(12) C(5)-C(4)-C(3) 119.6(8) C(2)-N(2)-C(13) 114.4(6)
C(6)-C(7) 1.537(14) N(3)-C(5)-C(4) 114.6(7) C(2)-N(2)-C(3) 112.4(7)
C(6)-N(3) 1.543(11) C(7)-C(6)-N(3) 111.1(6) C(13)-N(2)-C(3) 109.5(7)
C(7)-N(4) 1.426(11) N(4)-C(7)-C(6) 115.1(8) C(2)-N(2)-Cu(1) 103.9(5)
C(8)-C(9) 1.468(14) C(9)-C(8)-N(4) 118.6(8) C(13)-N(2)-Cu(1) 105.3(5)
C(8)-N(4) 1.515(12) C(8)-C(9)-C(10) 119.6(8) C(3)-N(2)-Cu(1) 111.0(5)
C(9)-C(10) 1.550(13) N(1)-C(10)-C(9) 113.9(7) C(5)-N(3)-C(12) 110.6(7)
C(10)-N(1) 1.488(12) N(1)-C(11)-C(12) 113.1(7) C(5)-N(3)-C(6) 104.5(6)
C(11)-N(1) 1.488(11) N(3)-C(12)-C(11) 112.9(7) C(12)-N(3)-C(6) 106.9(7)
C(11)-C(12) 1.505(11) N(2)-C(13)-C(14) 114.2(7) C(5)-N(3)-Cu(1) 115.5(6)
C(12)-N(3) 1.493(11) C(19)-C(14)-C(15) 118.8(7) C(12)-N(3)-Cu(1) 111.5(4)
C(13)-N(2) 1.472(11) C(19)-C(14)-C(13) 120.3(7) C(6)-N(3)-Cu(1) 107.2(5)
C(13)-C(14) 1.529(11) C(15)-C(14)-C(13) 120.9(7) C(7)-N(4)-C(20) 115.2(7)
C(14)-C(19) 1.378(10) C(16)-C(15)-C(14) 118.4(7) C(7)-N(4)-C(8) 111.7(8)
C(14)-C(15) 1.418(11) C(17)-C(16)-C(15) 123.8(7) C(20)-N(4)-C(8) 111.5(7)
C(15)-C(16) 1.371(12) C(17)-C(16)-Br(1) 117.8(6) C(7)-N(4)-Cu(1) 103.1(6)
C(16)-C(17) 1.368(10) C(15)-C(16)-Br(1) 118.3(5) C(20)-N(4)-Cu(1) 108.8(5)
C(16)-Br(1) 1.909(8) C(16)-C(17)-C(18) 117.0(7) C(8)-N(4)-Cu(1) 105.7(5)
C(17)-C(18) 1.394(11) C(19)-C(18)-C(17) 121.3(6) N(1)-Cu(1)-N(3) 83.2(3)
C(18)-C(19) 1.383(11) C(19)-C(18)-Br(2) 120.2(6) N(1)-Cu(1)-Cl(2) 168.5(2)
C(18)-Br(2) 1.880(7) C(17)-C(18)-Br(2) 118.5(6) N(3)-Cu(1)-Cl(2) 93.3(2)
C(20)-N(4) 1.477(11) C(14)-C(19)-C(18) 120.6(7) N(1)-Cu(1)-Cl(1) 92.47(18)
C(20)-C(21) 1.519(11) N(4)-C(20)-C(21) 115.5(7) N(3)-Cu(1)-Cl(1) 167.8(2)
C(21)-C(22) 1.386(11) C(22)-C(21)-C(26) 118.2(7) Cl(2)-Cu(1)-Cl(1) 93.12(8)
C(21)-C(26) 1.390(10) C(22)-C(21)-C(20) 121.8(6) N(1)-Cu(1)-N(2) 79.3(3)
C(22)-C(23) 1.380(11) C(26)-C(21)-C(20) 119.9(7) N(3)-Cu(1)-N(2) 92.0(3)
C(23)-C(24) 1.392(10) C(23)-C(22)-C(21) 119.8(6) Cl(2)-Cu(1)-N(2) 89.94(18)
C(23)-Br(3) 1.900(8) C(22)-C(23)-C(24) 122.3(7) Cl(1)-Cu(1)-N(2) 98.41(17)
C(24)-C(25) 1.378(11) C(22)-C(23)-Br(3) 119.8(5) N(1)-Cu(1)-N(4) 95.9(3)
C(25)-C(26) 1.367(12) C(24)-C(23)-Br(3) 117.9(6) N(3)-Cu(1)-N(4) 79.8(3)
C(25)-Br(4) 1.898(7) C(25)-C(24)-C(23) 116.6(7) Cl(2)-Cu(1)-N(4) 94.14(19)
N(1)-Cu(1) 2.071(7) C(26)-C(25)-C(24) 122.1(6) Cl(1)-Cu(1)-N(4) 89.43(17)
N(2)-Cu(1) 2.455(8) C(26)-C(25)-Br(4) 120.4(6) N(2)-Cu(1)-N(4) 171.0(2)
N(3)-Cu(1) 2.091(7) C(24)-C(25)-Br(4) 117.3(6)
N(4)-Cu(1) 2.495(8) C(25)-C(26)-C(21) 120.9(7)
Table S2. Bond lengths (Å) and angles (°) for [Cu2Cl2]
S7
4. References
[1] C.A. Hunter and J.K.M. Sanders, J. Am. Chem. Soc. 112 (1990) 5525.
[2] B.H. Ye, X.M. Chen, G.Q. Xue and L.N. Ji, Dalton Trans. (1998) 2827.


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Inclusion complexes of ortho-anisidine and β-cyclodextrin: A quantum mechanical calculation

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Structural characterization and activation energy of NiTiO3 nanopowders prepared by the co-precipitation and impregnation with calcinations

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Effect of physical chemistry parameters in photocatalytic properties of TiO<sub>2</sub> nanocrystals

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