Stephen F. Nelsen, Asgeir E. Konradsson, Rustem F. Ismagilov, Ilia A. Guzei N N

Transcription

1 Supporting information for: Crystallographic characterization of the geometry changes upon electron loss from 2-tertbutyl-3-aryl-2,3-diazabicyclo[2.2.2]octanes Stephen F. Nelsen, Asgeir E. Konradsson, Rustem F. Ismagilov, Ilia A. Guzei Discussion: R 4 N 2 (0,+1) geometry changes characterized by x-ray crystallography Although R 4 N + 2 persist for hours in solution, S1 they cannot be isolated as salts unless special alkyl groups are present that limit the rate of proton transfer between the tiny amount of the disproportionation products, R 4 N 0 2 and R 4 N 2+ 2, formed upon intermolecular transfer between R 4 N + 2, a process which is about 20 kcal/mol endoenergetic for many examples. This was first achieved using Bredt s rule kinetic protection, placing the nitrogens in N,N-bicyclic systems so the α-hydrogens in the dications were at bridgehead carbons for which proton loss is kinetically inhibited. S2 The large α-branched alkyl groups in these compounds destabilize the electronically preferred θ ~ 90 neutral conformation so much that they exist in anti θ = 180 conformations in both their 0 and +1 oxidation levels. S3 Although Bredt s rule protection led to radical cation crystals that diffracted, undetected disorder led to incorrect assignment of the nitrogens as being planar, which misled us about the nature of these species for a few years. We finally realized our error when the dimeric diazabicyclooctane salt 1 + PF - 6 was disordered in the same way as the 2 + originally studied, and were able to characterize N N N N N N S1 (32N) 2 S2 (33N) 2 S3 (AdN) 2 the geometry change upon electron removal in three N,N -bis-bicyclic systems (See Table 1). The most interesting thing conformationally about 1 is that it crystallizes in the diaxial conformation (each NR 2 axial to the adjacent six-membered ring) shown, despite Table S1. N,N -bis(bicyclic) hydrazines (θ 0 ~ 180 ) (321N) a 1 + NO - 3 H 2 O a Difference d(nn), Å 1.469(2) 1.323(4) (9.9%) α av, 12.1(1) 4.4(2) -7.7 (73%) θ (331N) b 2 + OTs - c d(nn), Å 1.505(3) 1.357(4) (9.8%) α av, 12.0(1) 3.7(3) -8.3 (79%) θ (AdN) d 3 + TsO - d d(nn), Å 1.512(2) 1.353(5) A (10.5%) 1.360(6) B (10.1%) α av, 11.65(12) 3.4(3) A (79%) 3.3(4) B (80%) θ a. Ref. S4. b. Ref. S3. c. previously unpublished. d. Ref. S5.

2 the fact that this is the least stable of the three θ = 180 o conformations in solution. S4 It is the most compact conformation according to calculations. The bis(azaadamantane) 3, S5 which has not been discussed previously shows rather similar geometrical changes to 2. Discovery of the proton-driven Diels-Alder reaction S6 allowed preparation of bis(n,n - bicyclic) (sequibicyclic) hydrazines, which have close to 0 θ values in their neutral forms, and x-ray characterization of both 0 and +1 oxidation levels of 4-6. S7,S8 N N S4 22/u22 N N S6 21/22 N N S5 22/22 N N S6 + 21/22 N N S7 22/31 N N S7 + 22/31 The dication 5 2+ is uniquely stable, S9 and not only could an x-ray structure be obtained, S7 but its deprotonation and hydride reduction of the resulting aminoaziridinium cation allowed preparation of 7 and structural characterization of both of its oxidation levels (see Table 2). S and 7 + are examples of several sesquibicyclic hydrazines for which Table S2. N,N -bis(bicyclic) hydrazines (θ 0 ~ 0 ) 22/u a a NO 3 d(nn), Å 1.497(4) 1.349(1) (9.9%) α av, 7.8(3),8.0(3) 2.5(1), 2.2(1) -5.6 (53%) θ NN, 0.2(4) 0.6(1) / a 5 + TsO - a d(nn), Å 1.492(2) (14)[A] 1.325(13)[B] (10.7%) α av, 6.5(1) 0.7(10),1.4(10)[A] (52%) 1.5(9),2.0(9)[B] θ N, 15.0(2) 1.9(1.4) [A] 5.5(1.2) [B] 21/ b c NO (45%) d(nn), Å 1.514(2) 1.341(3) [A] (11.4%)[A] 1.335(4) [B] (11.8%)[B] α av, 9.7(1) 1.7(2),2.1(3)[A] (76%)[A] 10.0(1) 1.7(3),1.4(3)[B] 8.3(79%[B] θ N, 1.0(2) 2.0(3) [A],-1.2(4)[B] (-1, -0.2) 22/13 7 d 7 + TsO - d d(nn), Å 1.500(3) 1.328(3) (11.5%) α av, 9.3 (2) (N 1 ) 9.7 (2) (N 2 ) 0.9 (2) (both) -8.6 (82%) θ NN, 4.3 (2) 0.7 (3) -3.6

3 a. Ref. S7. b. Ref. S8. c. Ref. S5. d. Ref. S10. the neutral form and radical cation exist in different double nitrogen inversion forms. The flatter nitrogens of the radical cation decrease 1,3 interactions and increase 1,2 interactions (bridgehead hydrogen NR 2 interaction is the important interaction) enough that which ring reversal form is most stable changes upon electron removal. Because the two ring reversal forms of the radical cation have different nitrogen pyramidalities, properties like the optical absorption spectra, which are especially sensitive to α av are rather different for the two double nitrogen inversion forms. Chen s discovery S11 that Bredt s rule protection is not necessary to allow radical cation isolation because tetra-α-branching suffices allows obtaining crystal structures for which the θ values of 0 and +1 oxidation levels are substantially different. S12 Compounds S8-S10 have been studied. These systems have significant flattening at the nitrogens ipr N N ipr N N N N S8 33NNiPr 2 S9 ipr 2 NNiPr 2 S10 chx 2 NNcHx 2 of the neutral oxidation level, leading to considerably smaller changes in both d(nn) and in α av than for the θ 0 ~ 0 or ~180 systems (see Table 3). The unlinked α-branched alkyl Table S3. Neutral θ 0 ~ 90 systems (33N)NiPr 2 S8(0) a - a S8(+) NO 3 difference d(nn), Å 1.420(2) 1.346(3) (-5.2%) α av, 4.7 (33N) 3.1 (33N) -1.6 (15%) 2.3 (NiPr 2 ) 1.2 (NiPr 2 ) -1.1 (10%) φ NN, ipr 2 NNiPr 2 S9(0) b S9(+) TsO - CH 3 CN d(nn), Å 1.394(4) [major] 1.399(5) [minor] 1.333(4) (-4.4% α av, 4.2 (3) [major] 4.2 (5) [minor] 0.1; (38%) φ NN, 88.5 (5) [major] [major] (8) [minor] 78.6 [minor] chx 2 NNcHx 2 S10(0) b S10(+) c - B[C 6 H 3 (CF 3 ) 2 ] 4 d(nn), Å 1.389(7) 1.333(9) (4.0%) α av, 3.3(5) [N 1 ] 0.0(3) 3.3 (31%) 3.4(5) [N 2 ] 3.4 (32%) φ NN, 89.4(7) 0.1(6) a. Ref. S11. b. Ref. S12. c. Ref. S5. groups adopt conformations been studied. Despite θ values near 90, that put one HCNN twist angle near 0 and the other at the same nitrogen near 180, to minimize non-bonded steric interactions. For S9 + each C α H bond is tucked between the substitutents of the adjacent alkyl groups, as indicated diagramatically below, which makes S9 + nearly isostructural with tetraisopropylethylene. S13 Although the nearly colorless tetrakis-

4 H H N N H S9 + (m,m -bis(trifluoromethyl)phenyl)borate salt of S10 + is in the same conformation, its dark red TsO -, and NO 3 - and SbF 6 - salts are in a twisted conformation because the alkyl groups are in a different conformation than S9 +. S5 Crystallographic Experimental Section HyDU + NO - 3 (97264) H

5 Table 1. Crystal data and structure refinement for Identification code Empirical formula C20 H32 N3 O3 Formula weight Temperature 133(2) K Wavelength Å Crystal system Monoclinic Space group P2 1 /c Unit cell dimensions a = (4) Å α= 90. b = (2) Å β= (2). c = (5) Å γ = 90. Volume (9) Å 3 Z 4 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 788 Crystal size 0.48 x 0.41 x 0.29 mm 3 Theta range for data collection 2.45 to Index ranges -20<=h<=21, -6<=k<=10, -12<=l<=21 Reflections collected 8955 Independent reflections 4393 [R(int) = ] Completeness to theta = % Absorption correction Multi-scan with SADABS Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4393 / 0 / 235 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq)

6 N(1) 7609(1) 6453(1) 5598(1) 15(1) N(2) 8315(1) 6936(1) 5407(1) 15(1) C(1) 9220(1) 6105(1) 5989(1) 18(1) C(2) 9484(1) 6482(2) 6977(1) 24(1) C(3) 8673(1) 5910(2) 7177(1) 25(1) C(4) 7896(1) 5176(1) 6320(1) 19(1) C(5) 9090(1) 4219(1) 5833(1) 20(1) C(6) 8263(1) 3649(1) 6019(1) 21(1) C(7) 6618(1) 6552(1) 4978(1) 16(1) C(8) 6263(1) 5843(1) 4119(1) 18(1) C(9) 5286(1) 5951(1) 3575(1) 21(1) C(10) 4716(1) 6693(1) 3910(1) 23(1) C(11) 5072(1) 7329(1) 4777(1) 20(1) C(12) 6045(1) 7292(1) 5324(1) 17(1) C(13) 6860(1) 4952(2) 3760(1) 23(1) C(14) 4846(1) 5253(2) 2636(1) 31(1) C(15) 4401(1) 8041(2) 5108(1) 28(1) C(16) 6458(1) 8047(2) 6253(1) 24(1) C(17) 8337(1) 8544(1) 4938(1) 18(1) C(18) 8704(1) 8108(2) 4257(1) 37(1) C(19) 7389(1) 9410(2) 4477(1) 34(1) C(20) 9024(1) 9738(1) 5641(1) 27(1) N(3) 1787(1) 8127(2) 1950(1) 29(1) O(1) 1246(1) 7504(1) 1209(1) 38(1) O(2) 2516(1) 7368(2) 2445(1) 67(1) O(3) 1585(1) 9487(2) 2177(1) 58(1) Table 3. Bond lengths [Å] and angles [ ] for N(1)-N(2) (12) N(1)-C(7) (13) N(1)-C(4) (13) N(2)-C(1) (13) N(2)-C(17) (13) C(1)-C(5) (15) C(1)-C(2) (15) C(1)-H(1) C(2)-C(3) (17) C(2)-H(2A) C(2)-H(2B) C(3)-C(4) (16) C(3)-H(3A) C(3)-H(3B) C(4)-C(6) (15) C(4)-H(4) C(5)-C(6) (15) C(5)-H(5A) C(5)-H(5B) C(6)-H(6A) C(6)-H(6B) C(7)-C(8) (15) C(7)-C(12) (14) C(8)-C(9) (15) C(8)-C(13) (15) C(9)-C(10) (17) C(9)-C(14) (16) C(10)-C(11) (17) C(10)-H(10) C(11)-C(12) (15) C(11)-C(15) (16) C(12)-C(16) (15) C(13)-H(13A) C(13)-H(13B) C(13)-H(13C) C(14)-H(14A) C(14)-H(14B) C(14)-H(14C) C(15)-H(15A) C(15)-H(15B) C(15)-H(15C) C(16)-H(16A) C(16)-H(16B) C(16)-H(16C) C(17)-C(19) (16) C(17)-C(18) (16) C(17)-C(20) (15) C(18)-H(18A) C(18)-H(18B) C(18)-H(18C) C(19)-H(19A) C(19)-H(19B) C(19)-H(19C) C(20)-H(20A)

7 C(20)-H(20B) C(20)-H(20C) N(3)-O(2) (15) N(2)-N(1)-C(7) (8) N(2)-N(1)-C(4) (8) C(7)-N(1)-C(4) (8) N(1)-N(2)-C(1) (8) N(1)-N(2)-C(17) (8) C(1)-N(2)-C(17) (8) N(2)-C(1)-C(5) (8) N(2)-C(1)-C(2) (9) C(5)-C(1)-C(2) (9) N(2)-C(1)-H(1) C(5)-C(1)-H(1) C(2)-C(1)-H(1) C(3)-C(2)-C(1) (9) C(3)-C(2)-H(2A) C(1)-C(2)-H(2A) C(3)-C(2)-H(2B) C(1)-C(2)-H(2B) H(2A)-C(2)-H(2B) C(4)-C(3)-C(2) (9) C(4)-C(3)-H(3A) C(2)-C(3)-H(3A) C(4)-C(3)-H(3B) C(2)-C(3)-H(3B) H(3A)-C(3)-H(3B) N(1)-C(4)-C(3) (9) N(1)-C(4)-C(6) (9) C(3)-C(4)-C(6) (9) N(1)-C(4)-H(4) C(3)-C(4)-H(4) C(6)-C(4)-H(4) C(1)-C(5)-C(6) (9) C(1)-C(5)-H(5A) C(6)-C(5)-H(5A) C(1)-C(5)-H(5B) C(6)-C(5)-H(5B) H(5A)-C(5)-H(5B) C(4)-C(6)-C(5) (9) C(4)-C(6)-H(6A) C(5)-C(6)-H(6A) C(4)-C(6)-H(6B) C(5)-C(6)-H(6B) H(6A)-C(6)-H(6B) C(8)-C(7)-C(12) (10) C(8)-C(7)-N(1) (9) C(12)-C(7)-N(1) (9) C(7)-C(8)-C(9) (10) C(7)-C(8)-C(13) (10) C(9)-C(8)-C(13) (10) C(10)-C(9)-C(8) (10) C(10)-C(9)-C(14) (10) C(8)-C(9)-C(14) (11) C(11)-C(10)-C(9) (10) N(3)-O(3) (17) N(3)-O(1) (15) C(11)-C(10)-H(10) C(9)-C(10)-H(10) C(10)-C(11)-C(12) (10) C(10)-C(11)-C(15) (10) C(12)-C(11)-C(15) (11) C(11)-C(12)-C(7) (10) C(11)-C(12)-C(16) (10) C(7)-C(12)-C(16) (10) C(8)-C(13)-H(13A) C(8)-C(13)-H(13B) H(13A)-C(13)-H(13B) C(8)-C(13)-H(13C) H(13A)-C(13)-H(13C) H(13B)-C(13)-H(13C) C(9)-C(14)-H(14A) C(9)-C(14)-H(14B) H(14A)-C(14)-H(14B) C(9)-C(14)-H(14C) H(14A)-C(14)-H(14C) H(14B)-C(14)-H(14C) C(11)-C(15)-H(15A) C(11)-C(15)-H(15B) H(15A)-C(15)-H(15B) C(11)-C(15)-H(15C) H(15A)-C(15)-H(15C) H(15B)-C(15)-H(15C) C(12)-C(16)-H(16A) C(12)-C(16)-H(16B) H(16A)-C(16)-H(16B) C(12)-C(16)-H(16C) H(16A)-C(16)-H(16C) H(16B)-C(16)-H(16C) N(2)-C(17)-C(19) (9) N(2)-C(17)-C(18) (9) C(19)-C(17)-C(18) (11) N(2)-C(17)-C(20) (9) C(19)-C(17)-C(20) (10) C(18)-C(17)-C(20) (10) C(17)-C(18)-H(18A) C(17)-C(18)-H(18B) H(18A)-C(18)-H(18B) C(17)-C(18)-H(18C) H(18A)-C(18)-H(18C) H(18B)-C(18)-H(18C) C(17)-C(19)-H(19A) C(17)-C(19)-H(19B) H(19A)-C(19)-H(19B) C(17)-C(19)-H(19C) H(19A)-C(19)-H(19C) H(19B)-C(19)-H(19C) C(17)-C(20)-H(20A) C(17)-C(20)-H(20B) 109.5

8 H(20A)-C(20)-H(20B) C(17)-C(20)-H(20C) H(20A)-C(20)-H(20C) H(20B)-C(20)-H(20C) O(2)-N(3)-O(3) (14) O(2)-N(3)-O(1) (14) O(3)-N(3)-O(1) (12)

9 Symmetry transformations used to generate equivalent atoms: Table 4. Anisotropic displacement parameters (Å 2 x 10 3 ) for The anisotropic displacement factor exponent takes the form: -2π 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 N(1) 14(1) 17(1) 14(1) 1(1) 7(1) 1(1) N(2) 13(1) 16(1) 15(1) 0(1) 6(1) 0(1) C(1) 13(1) 20(1) 19(1) 1(1) 5(1) 2(1) C(2) 22(1) 25(1) 17(1) -1(1) 1(1) 1(1) C(3) 28(1) 30(1) 13(1) 2(1) 7(1) 6(1) C(4) 20(1) 21(1) 18(1) 6(1) 10(1) 4(1) C(5) 19(1) 18(1) 22(1) 0(1) 9(1) 4(1) C(6) 23(1) 18(1) 24(1) 3(1) 11(1) 1(1) C(7) 13(1) 15(1) 17(1) 1(1) 6(1) 0(1) C(8) 19(1) 16(1) 18(1) 0(1) 8(1) -1(1) C(9) 20(1) 18(1) 20(1) 1(1) 4(1) -3(1) C(10) 14(1) 20(1) 29(1) 4(1) 4(1) -1(1) C(11) 17(1) 16(1) 30(1) 4(1) 12(1) 2(1) C(12) 18(1) 15(1) 21(1) 1(1) 10(1) 1(1) C(13) 23(1) 26(1) 19(1) -6(1) 9(1) -1(1) C(14) 27(1) 34(1) 22(1) -3(1) 1(1) -4(1) C(15) 21(1) 24(1) 45(1) 3(1) 20(1) 3(1) C(16) 25(1) 26(1) 23(1) -3(1) 13(1) 4(1) C(17) 20(1) 18(1) 18(1) 2(1) 9(1) -3(1) C(18) 65(1) 29(1) 36(1) -3(1) 39(1) -9(1) C(19) 22(1) 26(1) 43(1) 19(1) 5(1) 0(1) C(20) 26(1) 18(1) 29(1) -1(1) 5(1) -4(1) N(3) 19(1) 42(1) 27(1) 12(1) 11(1) -4(1) O(1) 28(1) 50(1) 34(1) -3(1) 11(1) 1(1) O(2) 22(1) 105(1) 59(1) 57(1) 6(1) 6(1) O(3) 53(1) 57(1) 76(1) -26(1) 39(1) -20(1) Table 5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for x y z U(eq) H(1) H(2A) H(2B) H(3A) H(3B) H(4) H(5A) H(5B) H(6A) H(6B) H(10) H(13A) H(13B) H(13C) H(14A)

10 H(14B) H(14C) H(15A) H(15B) H(15C) H(16A) H(16B) H(16C) H(18A) H(18B) H(18C) H(19A) H(19B) H(19C) H(20A) H(20B) H(20C) Table 6. Torsion angles [ ] for C(7)-N(1)-N(2)-C(1) (9) C(4)-N(1)-N(2)-C(1) -1.79(11) C(7)-N(1)-N(2)-C(17) 45.14(14) C(4)-N(1)-N(2)-C(17) (9) N(1)-N(2)-C(1)-C(5) 60.96(11) C(17)-N(2)-C(1)-C(5) (9) N(1)-N(2)-C(1)-C(2) (11) C(17)-N(2)-C(1)-C(2) (10) N(2)-C(1)-C(2)-C(3) 56.59(12) C(5)-C(1)-C(2)-C(3) (11) C(1)-C(2)-C(3)-C(4) -0.10(13) N(2)-N(1)-C(4)-C(3) 60.56(11) C(7)-N(1)-C(4)-C(3) (9) N(2)-N(1)-C(4)-C(6) (11) C(7)-N(1)-C(4)-C(6) 98.14(10) C(2)-C(3)-C(4)-N(1) (12) C(2)-C(3)-C(4)-C(6) 61.72(12) N(2)-C(1)-C(5)-C(6) (11) C(2)-C(1)-C(5)-C(6) 62.64(11) N(1)-C(4)-C(6)-C(5) 57.96(11) C(3)-C(4)-C(6)-C(5) (12) C(1)-C(5)-C(6)-C(4) -1.77(12) N(2)-N(1)-C(7)-C(8) 53.23(14) C(4)-N(1)-C(7)-C(8) (11) N(2)-N(1)-C(7)-C(12) (10) C(4)-N(1)-C(7)-C(12) 74.45(12) C(12)-C(7)-C(8)-C(9) 2.52(16) N(1)-C(7)-C(8)-C(9) (9) C(12)-C(7)-C(8)-C(13) (10) N(1)-C(7)-C(8)-C(13) -0.76(16) C(7)-C(8)-C(9)-C(10) -1.93(16) C(13)-C(8)-C(9)-C(10) (10) C(7)-C(8)-C(9)-C(14) (10) C(13)-C(8)-C(9)-C(14) -2.55(16) C(8)-C(9)-C(10)-C(11) -0.69(17) C(14)-C(9)-C(10)-C(11) (11)

11 C(9)-C(10)-C(11)-C(12) 2.84(17) C(9)-C(10)-C(11)-C(15) (10) C(10)-C(11)-C(12)-C(7) -2.23(15) C(15)-C(11)-C(12)-C(7) (10) C(10)-C(11)-C(12)-C(16) (10) C(15)-C(11)-C(12)-C(16) -3.01(16) C(8)-C(7)-C(12)-C(11) -0.44(16) N(1)-C(7)-C(12)-C(11) (9) C(8)-C(7)-C(12)-C(16) (10) N(1)-C(7)-C(12)-C(16) 4.69(14) N(1)-N(2)-C(17)-C(19) (15) C(1)-N(2)-C(17)-C(19) (10) N(1)-N(2)-C(17)-C(18) (11) C(1)-N(2)-C(17)-C(18) 66.35(12) N(1)-N(2)-C(17)-C(20) (11) C(1)-N(2)-C(17)-C(20) (12) Symmetry transformations used to generate equivalent atoms: Hy 1 NA + SbF 6 - (98001)

12 Table 1. Crystal data and structure refinement for Identification code Empirical formula C20 H26 F6 N2 Sb Formula weight Temperature 133(2) K Wavelength Å Crystal system Orthorhombic Space group Pbca Unit cell dimensions a = (18) Å α= 90. b = (16) Å β= 90. c = (17) Å γ = 90. Volume (8) Å 3 Z 8 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 2120 Crystal size 0.42 x 0.14 x 0.01 mm 3 Theta range for data collection 2.78 to Index ranges -15<=h<=18, -19<=k<=11, -19<=l<=13 Reflections collected Independent reflections 3763 [R(int) = ] Completeness to theta = % Absorption correction Multi-scan with SADABS Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 3763 / 0 / 262 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3

13 Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) Sb(1) 6854(1) 3277(1) 5962(1) 35(1) F(1) 7854(3) 3500(3) 6520(3) 54(2) F(2) 5845(4) 3083(4) 5409(4) 93(3) F(3) 6529(5) 4368(4) 6137(5) 92(2) F(4) 7144(4) 2179(4) 5884(4) 76(2) F(5) 6313(4) 3001(4) 6933(3) 72(2) F(6) 7330(4) 3554(5) 4981(3) 96(3) C(1) 4156(4) 4810(5) 7491(5) 31(2) N(2) 4857(4) 5405(3) 7539(3) 21(1) N(3) 4810(4) 5992(4) 6966(3) 23(1) C(4) 4068(5) 5895(5) 6433(4) 28(2) C(5) 4103(5) 5050(5) 6018(5) 37(2) C(6) 4187(5) 4403(5) 6663(5) 32(2) C(7) 3318(5) 5263(5) 7598(5) 31(2) C(8) 3270(4) 5941(5) 6964(4) 30(2) C(9) 5181(5) 5601(5) 8346(4) 24(2) C(10) 4879(5) 6270(5) 8734(5) 32(2) C(11) 5188(5) 6430(6) 9532(5) 41(2) C(12) 5756(6) 5929(6) 9886(5) 46(2) C(13) 6670(5) 4694(7) 9828(5) 51(3) C(14) 6967(6) 4037(7) 9419(6) 56(3) C(15) 6668(5) 3840(5) 8619(6) 41(2) C(16) 6087(5) 4358(5) 8274(5) 33(2) C(17) 5768(4) 5040(5) 8686(4) 26(2) C(18) 6068(5) 5222(6) 9487(4) 34(2) C(19) 5544(4) 6530(4) 6712(4) 21(2) C(20) 5774(5) 6311(5) 5838(4) 32(2) C(21) 5243(5) 7415(5) 6767(5) 37(2) C(22) 6322(5) 6395(5) 7234(5) 35(2)

14 Table 3. Bond lengths [Å] and angles [ ] for Sb(1)-F(6) 1.841(5) C(10)-C(11) 1.428(11) Sb(1)-F(4) 1.859(6) C(10)-H(10) Sb(1)-F(1) 1.866(5) C(11)-C(12) 1.349(12) Sb(1)-F(2) 1.866(5) C(11)-H(11) Sb(1)-F(5) 1.872(5) C(12)-C(18) 1.420(13) Sb(1)-F(3) 1.881(6) C(12)-H(12) C(1)-N(2) 1.479(9) C(13)-C(14) 1.354(14) C(1)-C(6) 1.522(11) C(13)-C(18) 1.403(12) C(1)-C(7) 1.529(10) C(13)-H(13) C(1)-H(1) C(14)-C(15) 1.437(14) N(2)-N(3) 1.349(8) C(14)-H(14) N(2)-C(9) 1.462(8) C(15)-C(16) 1.374(10) N(3)-C(4) 1.474(9) C(15)-H(15) N(3)-C(19) 1.517(9) C(16)-C(17) 1.401(11) C(4)-C(8) 1.538(10) C(16)-H(16) C(4)-C(5) 1.544(11) C(17)-C(18) 1.436(10) C(4)-H(4) C(19)-C(22) 1.517(10) C(5)-C(6) 1.507(11) C(19)-C(21) 1.528(10) C(5)-H(5A) C(19)-C(20) 1.529(10) C(5)-H(5B) C(20)-H(20A) C(6)-H(6A) C(20)-H(20B) C(6)-H(6B) C(20)-H(20C) C(7)-C(8) 1.527(10) C(21)-H(21A) C(7)-H(7A) C(21)-H(21B) C(7)-H(7B) C(21)-H(21C) C(8)-H(8A) C(22)-H(22A) C(8)-H(8B) C(22)-H(22B) C(9)-C(10) 1.356(11) C(22)-H(22C) C(9)-C(17) 1.421(10) F(6)-Sb(1)-F(4) 94.4(3) F(6)-Sb(1)-F(1) 92.2(3) F(4)-Sb(1)-F(1) 90.8(2) F(6)-Sb(1)-F(2) 87.8(3) F(4)-Sb(1)-F(2) 90.7(3) F(1)-Sb(1)-F(2) 178.4(3) F(6)-Sb(1)-F(5) 176.9(3) F(4)-Sb(1)-F(5) 86.5(3) F(1)-Sb(1)-F(5) 90.7(3) F(2)-Sb(1)-F(5) 89.2(3) F(6)-Sb(1)-F(3) 90.7(4) F(4)-Sb(1)-F(3) 174.8(3) F(1)-Sb(1)-F(3) 88.3(3) F(2)-Sb(1)-F(3) 90.2(3) F(5)-Sb(1)-F(3) 88.5(3) N(2)-C(1)-C(6) 108.2(6) N(2)-C(1)-C(7) 108.9(6) C(6)-C(1)-C(7) 110.1(6) N(2)-C(1)-H(1) C(6)-C(1)-H(1) C(7)-C(1)-H(1) N(3)-N(2)-C(9) 120.1(6) N(3)-N(2)-C(1) 113.0(6) C(9)-N(2)-C(1) 117.1(6) N(2)-N(3)-C(4) 112.7(6) N(2)-N(3)-C(19) 124.3(5) C(4)-N(3)-C(19) 120.5(5) N(3)-C(4)-C(8) 107.9(5) N(3)-C(4)-C(5) 109.5(6) C(8)-C(4)-C(5) 109.0(6) N(3)-C(4)-H(4) C(8)-C(4)-H(4) C(5)-C(4)-H(4) C(6)-C(5)-C(4) 108.7(6) C(6)-C(5)-H(5A) C(4)-C(5)-H(5A) C(6)-C(5)-H(5B) C(4)-C(5)-H(5B) H(5A)-C(5)-H(5B) C(5)-C(6)-C(1) 108.8(6) C(5)-C(6)-H(6A) C(1)-C(6)-H(6A) C(5)-C(6)-H(6B) C(1)-C(6)-H(6B) H(6A)-C(6)-H(6B) C(8)-C(7)-C(1) 108.4(6) C(8)-C(7)-H(7A) C(1)-C(7)-H(7A) 110.0

15 C(8)-C(7)-H(7B) C(1)-C(7)-H(7B) H(7A)-C(7)-H(7B) C(7)-C(8)-C(4) 108.3(6) C(7)-C(8)-H(8A) C(4)-C(8)-H(8A) C(7)-C(8)-H(8B) C(4)-C(8)-H(8B) H(8A)-C(8)-H(8B) C(10)-C(9)-C(17) 124.5(7) C(10)-C(9)-N(2) 118.9(7) C(17)-C(9)-N(2) 116.5(6) C(9)-C(10)-C(11) 117.6(8) C(9)-C(10)-H(10) C(11)-C(10)-H(10) C(12)-C(11)-C(10) 121.0(8) C(12)-C(11)-H(11) C(10)-C(11)-H(11) C(11)-C(12)-C(18) 121.8(7) C(11)-C(12)-H(12) C(18)-C(12)-H(12) C(14)-C(13)-C(18) 121.6(8) C(14)-C(13)-H(13) C(18)-C(13)-H(13) C(13)-C(14)-C(15) 121.5(8) C(13)-C(14)-H(14) C(15)-C(14)-H(14) C(16)-C(15)-C(14) 117.4(9) C(16)-C(15)-H(15) C(14)-C(15)-H(15) C(15)-C(16)-C(17) 122.2(8) C(15)-C(16)-H(16) C(17)-C(16)-H(16) C(16)-C(17)-C(9) 124.0(7) C(16)-C(17)-C(18) 119.5(7) C(9)-C(17)-C(18) 116.4(7) C(13)-C(18)-C(12) 123.6(8) C(13)-C(18)-C(17) 117.7(9) C(12)-C(18)-C(17) 118.7(7) C(22)-C(19)-N(3) 112.3(5) C(22)-C(19)-C(21) 111.0(6) N(3)-C(19)-C(21) 107.2(6) C(22)-C(19)-C(20) 108.0(6) N(3)-C(19)-C(20) 107.8(6) C(21)-C(19)-C(20) 110.6(6) C(19)-C(20)-H(20A) C(19)-C(20)-H(20B) H(20A)-C(20)-H(20B) C(19)-C(20)-H(20C) H(20A)-C(20)-H(20C) H(20B)-C(20)-H(20C) C(19)-C(21)-H(21A) C(19)-C(21)-H(21B) H(21A)-C(21)-H(21B) C(19)-C(21)-H(21C) H(21A)-C(21)-H(21C) H(21B)-C(21)-H(21C) C(19)-C(22)-H(22A) C(19)-C(22)-H(22B) H(22A)-C(22)-H(22B) C(19)-C(22)-H(22C) H(22A)-C(22)-H(22C) H(22B)-C(22)-H(22C) 109.5

16 Symmetry transformations used to generate equivalent atoms:

17 Table 4. Anisotropic displacement parameters (Å 2 x 10 3 ) for The anisotropic displacement factor exponent takes the form: -2π 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 Sb(1) 27(1) 40(1) 39(1) 8(1) -6(1) 5(1) F(1) 47(3) 64(4) 50(3) -10(3) -19(3) -3(3) F(2) 47(4) 120(6) 112(5) 64(5) -46(4) -26(4) F(3) 93(5) 47(4) 136(6) 19(4) -3(5) 25(3) F(4) 83(4) 59(4) 87(4) -38(3) -36(4) 26(3) F(5) 86(5) 69(4) 60(4) 2(3) 29(3) -13(3) F(6) 68(4) 181(8) 39(3) 19(4) 5(3) -44(5) C(1) 22(4) 36(4) 33(4) 10(4) -1(4) -4(4) N(2) 17(3) 20(3) 26(3) -2(3) -4(3) 3(2) N(3) 18(3) 33(4) 19(3) 8(3) -2(3) 1(3) C(4) 22(4) 44(5) 16(4) 15(4) -3(3) -3(4) C(5) 30(4) 54(5) 27(4) -18(4) 5(4) -5(4) C(6) 23(4) 29(4) 43(5) -4(4) -10(4) -9(4) C(7) 24(5) 41(5) 29(4) 7(4) -2(3) -10(4) C(8) 15(4) 42(5) 31(4) 5(4) 0(3) 3(4) C(9) 23(4) 39(5) 10(3) 1(3) -1(3) -12(4) C(10) 32(5) 33(5) 32(4) -2(4) 3(4) -3(4) C(11) 33(5) 58(6) 32(5) -20(4) 3(4) -11(4) C(12) 43(6) 76(7) 18(4) -4(5) -5(4) -16(5) C(13) 34(6) 93(8) 27(5) 28(5) -10(4) -15(5) C(14) 31(5) 69(7) 68(6) 57(6) -14(5) -14(5) C(15) 28(5) 33(5) 63(6) 17(4) -13(4) 3(4) C(16) 26(5) 23(4) 51(5) 18(4) -8(4) -8(4) C(17) 19(4) 34(5) 25(4) 20(3) 0(3) -8(3) C(18) 18(4) 65(6) 20(4) 17(4) -7(3) -18(4) C(19) 20(4) 20(4) 24(4) 7(3) 3(3) -2(3) C(20) 20(4) 43(5) 34(5) 2(4) 5(3) -3(4) C(21) 44(5) 29(5) 38(5) 9(4) 11(4) 0(4) C(22) 17(4) 55(5) 34(4) 18(4) -2(3) -8(4)

18 Table 5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for x y z U(eq) H(1) H(4) H(5A) H(5B) H(6A) H(6B) H(7A) H(7B) H(8A) H(8B) H(10) H(11) H(12) H(13) H(14) H(15) H(16) H(20A) H(20B) H(20C) H(21A) H(21B) H(21C) H(22A) H(22B) H(22C)

19 Table 6. Torsion angles [ ] for C(6)-C(1)-N(2)-N(3) 60.0(8) C(7)-C(1)-N(2)-N(3) -59.7(8) C(6)-C(1)-N(2)-C(9) (6) C(7)-C(1)-N(2)-C(9) 86.2(7) C(9)-N(2)-N(3)-C(4) (6) C(1)-N(2)-N(3)-C(4) 0.0(8) C(9)-N(2)-N(3)-C(19) 53.4(9) C(1)-N(2)-N(3)-C(19) (6) N(2)-N(3)-C(4)-C(8) 60.2(8) C(19)-N(3)-C(4)-C(8) (6) N(2)-N(3)-C(4)-C(5) -58.3(7) C(19)-N(3)-C(4)-C(5) 104.4(7) N(3)-C(4)-C(5)-C(6) 54.3(8) C(8)-C(4)-C(5)-C(6) -63.6(8) C(4)-C(5)-C(6)-C(1) 3.3(8) N(2)-C(1)-C(6)-C(5) -59.2(8) C(7)-C(1)-C(6)-C(5) 59.8(8) N(2)-C(1)-C(7)-C(8) 55.4(8) C(6)-C(1)-C(7)-C(8) -63.0(8) C(1)-C(7)-C(8)-C(4) 2.1(8) N(3)-C(4)-C(8)-C(7) -59.0(8) C(5)-C(4)-C(8)-C(7) 59.8(8) N(3)-N(2)-C(9)-C(10) 48.0(9) C(1)-N(2)-C(9)-C(10) -95.4(8) N(3)-N(2)-C(9)-C(17) (6) C(1)-N(2)-C(9)-C(17) 81.5(8) C(17)-C(9)-C(10)-C(11) 1.5(11) N(2)-C(9)-C(10)-C(11) 178.1(6) C(9)-C(10)-C(11)-C(12) -0.4(12) C(10)-C(11)-C(12)-C(18) -0.3(13) C(18)-C(13)-C(14)-C(15) -1.1(13) C(13)-C(14)-C(15)-C(16) 1.9(12) C(14)-C(15)-C(16)-C(17) -2.1(11) C(15)-C(16)-C(17)-C(9) 178.6(7) C(15)-C(16)-C(17)-C(18) 1.6(11) C(10)-C(9)-C(17)-C(16) (7) N(2)-C(9)-C(17)-C(16) 4.5(10) C(10)-C(9)-C(17)-C(18) -1.8(10) N(2)-C(9)-C(17)-C(18) (6) C(14)-C(13)-C(18)-C(12) (8) C(14)-C(13)-C(18)-C(17) 0.5(12) C(11)-C(12)-C(18)-C(13) 178.8(8) C(11)-C(12)-C(18)-C(17) 0.0(12) C(16)-C(17)-C(18)-C(13) -0.7(10) C(9)-C(17)-C(18)-C(13) (7) C(16)-C(17)-C(18)-C(12) 178.2(7) C(9)-C(17)-C(18)-C(12) 1.0(10) N(2)-N(3)-C(19)-C(22) -5.8(9) C(4)-N(3)-C(19)-C(22) (6) N(2)-N(3)-C(19)-C(21) (7) C(4)-N(3)-C(19)-C(21) 71.6(8) N(2)-N(3)-C(19)-C(20) 113.0(7) C(4)-N(3)-C(19)-C(20) -47.5(8)

20

21 Hy 2 NA + SbF - 6 (Nel011) Data Collection A black crystal with approximate dimensions 0.41 x 0.38 x 0.35 mm 3 was selected under oil under ambient conditions and attached to the tip of a nylon loop. The crystal was mounted in a stream of cold nitrogen at 100(2) K and centered in the X-ray beam by using a video camera. The crystal evaluation and data collection were performed on a Bruker CCD-1000 diffractometer with Mo K α (λ = Å) radiation and the diffractometer to crystal distance of 4.9 cm. The initial cell constants were obtained from three series of ω scans at different starting angles. Each series consisted of 20 frames collected at intervals of 0.3º in a 6º range about ω with the exposure time of 10 seconds per frame. A total of 54 reflections was obtained. The reflections were successfully indexed by an automated indexing routine built in the SMART program. The final cell constants were calculated from a set of 6454 strong reflections from the actual data collection. The data were collected by using the hemisphere data collection routine. The reciprocal space was surveyed to the extent of a full sphere to a resolution of 0.80 Å. A total of data were harvested by collecting three sets of frames with 0.3º scans in ω with an exposure time eight seconds per frame. These highly redundant datasets were corrected for Lorentz and polarization effects. The absorption correction was based on fitting a function to the empirical transmission surface as sampled by multiple equivalent measurements. 14 Structure Solution and Refinement The systematic absences in the diffraction data were consistent for the space groups Cc and C2/c. The E-statistics strongly suggested the centrosymmetric space group C2/c that yielded chemically reasonable and computationally stable results of refinement [1]. A successful solution by the direct methods provided most non-hydrogen atoms from the E-map. The remaining non-hydrogen atoms were located in an alternating series of least-squares cycles and difference Fourier maps. All non-hydrogen atoms were refined with anisotropic displacement coefficients. All hydrogen atoms were included in the structure factor calculation at idealized positions and were allowed to ride on the neighboring atoms with relative isotropic displacement

22 coefficients. There are two half-ions of SbF - 6 in the asymmetric unit. The Sb(1) anion occupies a crystallographic 2-fold axis while the Sb(2) anion resides on a crystallographic inversion center. Atoms F(2), F(3), and F(4) are equally disordered over two positions each; the Sb(1) moiety was refined with soft restraints. The final least-squares refinement of 572 parameters against 6071 data resulted in residuals R (based on F 2 for I 2σ) and wr (based on F 2 for all data) of and , respectively. The final difference Fourier map was featureless. Table 1. Crystal data and structure refinement for nel11. Identification code nel11 Empirical formula C 20 H 26 F 6 N 2 Sb Formula weight Temperature 100(2) K Wavelength Å Crystal system Monoclinic Space group C2/c Unit cell dimensions a = (3) Å α= 90. b = (18) Å β= (2). c = (2) Å γ = 90. Volume (10) Å 3 Z 8 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 2120 Crystal size 0.41 x 0.38 x 0.35 mm 3 Theta range for data collection 2.20 to Index ranges -28<=h<=27, -17<=k<=17, -20<=l<=20 Reflections collected Independent reflections 4386 [R(int) = ] Completeness to theta = % Absorption correction Multiscan with SADABS Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4386 / 6 / 291 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for nel11. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) Sb(1) (1) (1) Sb(2) (1) F(1) 1008(1) 1636(2) 3204(2) 38(1) F(2) -43(9) 2923(2) 2256(9) 65(3) F(3) -73(6) 1916(6) 1329(5) 54(2)

23 F(3A) -76(5) 1386(7) 1327(4) 67(3) F(4) -93(6) 391(2) 2184(6) 73(4) F(5) 2793(1) 1245(2) 333(2) 30(1) F(6) 2429(2) 2581(2) 1095(2) 31(1) F(7) 3458(1) 2898(2) 815(2) 34(1) N(1) 2824(1) 4270(2) 3464(2) 14(1) N(2) 2684(2) 4687(2) 2624(2) 16(1) C(1) 2347(2) 3512(2) 3457(3) 16(1) C(2) 2771(2) 2586(2) 3764(3) 23(1) C(3) 2186(2) 3795(3) 4221(3) 24(1) C(4) 1654(2) 3377(2) 2412(3) 23(1) C(5) 3586(2) 4363(2) 4329(3) 18(1) C(6) 3735(2) 5417(3) 4503(3) 23(1) C(7) 3628(2) 5855(2) 3555(3) 25(1) C(8) 3336(2) 5086(3) 2741(3) 21(1) C(9) 3876(2) 4292(3) 3055(3) 26(1) C(10) 4084(2) 3915(3) 4077(3) 22(1) C(11) 2011(2) 5162(2) 1958(2) 16(1) C(12) 1693(2) 5655(2) 2332(3) 16(1) C(13) 1023(2) 6105(2) 1662(3) 17(1) C(14) 661(2) 6611(2) 2006(3) 21(1) C(15) 14(2) 7033(3) 1339(3) 23(1) C(16) -306(2) 6972(3) 300(3) 25(1) C(17) 31(2) 6500(2) -57(3) 22(1) C(18) 701(2) 6050(2) 609(3) 18(1) C(19) 1065(2) 5549(2) 263(3) 20(1) C(20) 1703(2) 5110(2) 912(3) 20(1)

24 Table 3. Bond lengths [Å] and angles [ ] for nel11. Sb(1)-F(2)# (3) N(2)-C(11) 1.437(4) Sb(1)-F(2) 1.847(3) N(2)-C(8) 1.486(4) Sb(1)-F(3)# (3) C(1)-C(4) 1.527(5) Sb(1)-F(3) 1.847(3) C(1)-C(3) 1.529(5) Sb(1)-F(3A) 1.847(3) C(1)-C(2) 1.537(5) Sb(1)-F(3A)# (3) C(5)-C(6) 1.531(5) Sb(1)-F(4) 1.847(3) C(5)-C(10) 1.538(5) Sb(1)-F(4)# (3) C(6)-C(7) 1.544(5) Sb(1)-F(1) 1.877(2) C(7)-C(8) 1.544(5) Sb(1)-F(1)# (2) C(8)-C(9) 1.523(5) Sb(2)-F(7)# (2) C(9)-C(10) 1.537(5) Sb(2)-F(7) 1.868(2) C(11)-C(12) 1.368(5) Sb(2)-F(6) 1.875(2) C(11)-C(20) 1.421(5) Sb(2)-F(6)# (2) C(12)-C(13) 1.417(5) Sb(2)-F(5)# (2) C(13)-C(14) 1.419(5) Sb(2)-F(5) 1.878(2) C(13)-C(18) 1.425(5) F(2)-F(2)# (17) C(14)-C(15) 1.366(5) F(3)-F(3A) 0.757(12) C(15)-C(16) 1.406(5) F(4)-F(4)# (18) C(16)-C(17) 1.365(6) N(1)-N(2) 1.347(4) C(17)-C(18) 1.416(5) N(1)-C(5) 1.482(4) C(18)-C(19) 1.424(5) N(1)-C(1) 1.521(4) C(19)-C(20) 1.360(5)

25 F(2)#1-Sb(1)-F(2) 21.8(5) F(2)#1-Sb(1)-F(3)#1 67.4(4) F(2)-Sb(1)-F(3)#1 89.0(4) F(2)#1-Sb(1)-F(3) 89.0(4) F(2)-Sb(1)-F(3) 67.4(4) F(3)#1-Sb(1)-F(3) 156.4(5) F(2)#1-Sb(1)-F(3A) 112.6(4) F(2)-Sb(1)-F(3A) 91.1(4) F(3)#1-Sb(1)-F(3A) 179.8(6) F(3)-Sb(1)-F(3A) 23.6(4) F(2)#1-Sb(1)-F(3A)#1 91.1(4) F(2)-Sb(1)-F(3A)# (4) F(3)#1-Sb(1)-F(3A)#1 23.6(4) F(3)-Sb(1)-F(3A)# (6) F(3A)-Sb(1)-F(3A)# (6) F(2)#1-Sb(1)-F(4) 176.7(5) F(2)-Sb(1)-F(4) 155.8(4) F(3)#1-Sb(1)-F(4) 114.4(5) F(3)-Sb(1)-F(4) 89.1(5) F(3A)-Sb(1)-F(4) 65.5(5) F(3A)#1-Sb(1)-F(4) 90.9(5) F(2)#1-Sb(1)-F(4)# (4) F(2)-Sb(1)-F(4)# (5) F(3)#1-Sb(1)-F(4)#1 89.1(5) F(3)-Sb(1)-F(4)# (5) F(3A)-Sb(1)-F(4)#1 90.9(5) F(3A)#1-Sb(1)-F(4)#1 65.5(5) F(4)-Sb(1)-F(4)#1 26.9(6) F(2)#1-Sb(1)-F(1) 89.0(6) F(2)-Sb(1)-F(1) 92.2(6) F(3)#1-Sb(1)-F(1) 90.6(4) F(3)-Sb(1)-F(1) 89.6(4) F(3A)-Sb(1)-F(1) 89.6(3) F(3A)#1-Sb(1)-F(1) 90.1(3) F(4)-Sb(1)-F(1) 93.7(4) F(4)#1-Sb(1)-F(1) 85.1(4) F(2)#1-Sb(1)-F(1)#1 92.2(6) F(2)-Sb(1)-F(1)#1 89.0(6) F(3)#1-Sb(1)-F(1)#1 89.6(4) F(3)-Sb(1)-F(1)#1 90.6(4) F(3A)-Sb(1)-F(1)#1 90.1(3) F(3A)#1-Sb(1)-F(1)#1 89.6(3) F(4)-Sb(1)-F(1)#1 85.1(4) F(4)#1-Sb(1)-F(1)#1 93.7(4) F(1)-Sb(1)-F(1)# (16) F(7)#2-Sb(2)-F(7) (11) F(7)#2-Sb(2)-F(6) 89.86(11) F(7)-Sb(2)-F(6) 90.14(11) F(7)#2-Sb(2)-F(6)# (11) F(7)-Sb(2)-F(6)# (11) F(6)-Sb(2)-F(6)# (2) F(7)#2-Sb(2)-F(5)# (11) F(7)-Sb(2)-F(5)# (11) F(6)-Sb(2)-F(5)# (9) F(6)#2-Sb(2)-F(5)# (9) F(7)#2-Sb(2)-F(5) 89.42(11)

26 F(7)-Sb(2)-F(5) 90.58(11) F(6)-Sb(2)-F(5) 89.58(9) F(6)#2-Sb(2)-F(5) 90.42(9) F(5)#2-Sb(2)-F(5) F(2)#1-F(2)-Sb(1) 79.1(3) F(3A)-F(3)-Sb(1) 78.2(2) F(3)-F(3A)-Sb(1) 78.2(2) F(4)#1-F(4)-Sb(1) 76.6(3) N(2)-N(1)-C(5) 113.1(3) N(2)-N(1)-C(1) 123.3(3) C(5)-N(1)-C(1) 120.4(3) N(1)-N(2)-C(11) 120.3(3) N(1)-N(2)-C(8) 113.4(3) C(11)-N(2)-C(8) 117.5(3) N(1)-C(1)-C(4) 111.8(3) N(1)-C(1)-C(3) 107.5(3) C(4)-C(1)-C(3) 111.4(3) N(1)-C(1)-C(2) 107.5(3) C(4)-C(1)-C(2) 107.8(3) C(3)-C(1)-C(2) 110.9(3) N(1)-C(5)-C(6) 106.1(3) N(1)-C(5)-C(10) 110.0(3) C(6)-C(5)-C(10) 109.9(3) C(5)-C(6)-C(7) 108.7(3) C(6)-C(7)-C(8) 108.2(3) N(2)-C(8)-C(9) 107.7(3) N(2)-C(8)-C(7) 106.9(3) C(9)-C(8)-C(7) 111.8(3) C(8)-C(9)-C(10) 108.4(3) C(5)-C(10)-C(9) 108.6(3) C(12)-C(11)-C(20) 122.1(3) C(12)-C(11)-N(2) 120.5(3) C(20)-C(11)-N(2) 117.4(3) C(11)-C(12)-C(13) 119.7(3) C(14)-C(13)-C(12) 122.1(3) C(14)-C(13)-C(18) 118.9(3) C(12)-C(13)-C(18) 119.0(3) C(15)-C(14)-C(13) 120.6(3) C(14)-C(15)-C(16) 120.5(4) C(17)-C(16)-C(15) 120.5(3) C(16)-C(17)-C(18) 120.7(3) C(17)-C(18)-C(19) 122.2(3) C(17)-C(18)-C(13) 118.8(3) C(19)-C(18)-C(13) 119.0(3) C(20)-C(19)-C(18) 121.5(3) C(19)-C(20)-C(11) 118.7(3) Symmetry transformations used to generate equivalent atoms: #1 -x,y,-z+1/2 #2 -x+1/2,-y+1/2,-z

27 Table 4. Anisotropic displacement parameters (Å 2 x 10 3 ) for nel11. The anisotropic displacement factor exponent takes the form: -2π 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 Sb(1) 20(1) 19(1) 20(1) 0 13(1) 0 Sb(2) 21(1) 12(1) 18(1) 2(1) 13(1) 3(1) F(1) 18(1) 56(2) 36(1) 7(1) 13(1) -3(1) F(2) 59(5) 36(3) 111(12) 43(4) 55(10) 14(5) F(3) 57(5) 89(6) 29(3) 10(4) 32(3) -10(5) F(3A) 25(3) 147(9) 27(3) -28(4) 14(3) 7(6) F(4) 33(6) 25(2) 139(11) -12(3) 37(8) 1(3) F(5) 47(2) 16(1) 35(1) 8(1) 28(1) 10(1) F(6) 50(2) 27(1) 30(1) 5(1) 31(1) 7(1) F(7) 22(1) 36(1) 34(1) 7(1) 9(1) -5(1) N(1) 15(1) 10(1) 16(1) 1(1) 9(1) -1(1) N(2) 19(2) 12(1) 19(2) 0(1) 12(1) -1(1) C(1) 19(2) 10(2) 21(2) 0(1) 12(2) -4(1) C(2) 28(2) 10(2) 30(2) 4(1) 16(2) 2(1) C(3) 30(2) 23(2) 25(2) -1(2) 20(2) -3(2) C(4) 23(2) 15(2) 26(2) 0(2) 12(2) -7(1) C(5) 16(2) 17(2) 20(2) 1(1) 9(2) 1(1) C(6) 21(2) 18(2) 27(2) -7(2) 11(2) -4(2) C(7) 23(2) 17(2) 32(2) -1(2) 14(2) -7(2) C(8) 20(2) 21(2) 26(2) 4(2) 15(2) -1(2) C(9) 24(2) 30(2) 32(2) 1(2) 19(2) 4(2) C(10) 18(2) 19(2) 32(2) 3(2) 15(2) 4(1) C(11) 18(2) 10(2) 19(2) 1(1) 10(1) -2(1) C(12) 20(2) 11(2) 17(2) -1(1) 10(1) -3(1) C(13) 19(2) 11(2) 18(2) -1(1) 9(2) -3(1) C(14) 22(2) 20(2) 20(2) 0(1) 11(2) 0(1) C(15) 22(2) 21(2) 30(2) 2(2) 16(2) 1(2) C(16) 17(2) 19(2) 32(2) 7(2) 10(2) -1(2) C(17) 20(2) 20(2) 18(2) 4(2) 5(2) -2(1) C(18) 17(2) 11(2) 22(2) 0(1) 8(2) -6(1) C(19) 24(2) 15(2) 15(2) -1(1) 8(2) -4(1) C(20) 25(2) 16(2) 24(2) -3(1) 17(2) -4(2) Table 5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for nel11. x y z U(eq) H(2A) H(2B) H(2C) H(3A) H(3B) H(3C) H(4A) H(4B) H(4C) H(5) H(6A) H(6B)

28 H(7A) H(7B) H(8) H(9A) H(9B) H(10A) H(10B) H(12) H(14) H(15) H(16) H(17) H(19) H(20) Table 6. Torsion angles [ ] for nel11.

29 F(3)#1-Sb(1)-F(2)-F(2)#1 9(3) F(3)-Sb(1)-F(2)-F(2)#1-170(3) F(3A)-Sb(1)-F(2)-F(2)#1-171(3) F(3A)#1-Sb(1)-F(2)-F(2)#1 9(3) F(4)-Sb(1)-F(2)-F(2)# (19) F(4)#1-Sb(1)-F(2)-F(2)#1-46(12) F(1)-Sb(1)-F(2)-F(2)#1-82(3) F(1)#1-Sb(1)-F(2)-F(2)#1 99(3) F(2)#1-Sb(1)-F(3)-F(3A) 178.8(16) F(2)-Sb(1)-F(3)-F(3A) (17) F(3)#1-Sb(1)-F(3)-F(3A) (15) F(3A)#1-Sb(1)-F(3)-F(3A) 87(100) F(4)-Sb(1)-F(3)-F(3A) -3.9(15) F(4)#1-Sb(1)-F(3)-F(3A) 5.4(17) F(1)-Sb(1)-F(3)-F(3A) 89.8(15) F(1)#1-Sb(1)-F(3)-F(3A) -89.0(15) F(2)#1-Sb(1)-F(3A)-F(3) -1.3(17) F(2)-Sb(1)-F(3A)-F(3) 2.2(16) F(3)#1-Sb(1)-F(3A)-F(3) 94(100) F(3A)#1-Sb(1)-F(3A)-F(3) (15) F(4)-Sb(1)-F(3A)-F(3) 175.7(16) F(4)#1-Sb(1)-F(3A)-F(3) (15) F(1)-Sb(1)-F(3A)-F(3) -90.1(15) F(1)#1-Sb(1)-F(3A)-F(3) 91.2(15) F(2)#1-Sb(1)-F(4)-F(4)#1-144(9) F(2)-Sb(1)-F(4)-F(4)# (16) F(3)#1-Sb(1)-F(4)-F(4)#1-21(2) F(3)-Sb(1)-F(4)-F(4)# (19) F(3A)-Sb(1)-F(4)-F(4)#1 159(2) F(3A)#1-Sb(1)-F(4)-F(4)#1-18.7(19) F(1)-Sb(1)-F(4)-F(4)#1 71.5(19) F(1)#1-Sb(1)-F(4)-F(4)# (19) C(5)-N(1)-N(2)-C(11) (3) C(1)-N(1)-N(2)-C(11) 57.4(4) C(5)-N(1)-N(2)-C(8) 3.9(4) C(1)-N(1)-N(2)-C(8) (3) N(2)-N(1)-C(1)-C(4) -7.2(4) C(5)-N(1)-C(1)-C(4) (3) N(2)-N(1)-C(1)-C(3) (3) C(5)-N(1)-C(1)-C(3) 71.7(4) N(2)-N(1)-C(1)-C(2) 110.9(3) C(5)-N(1)-C(1)-C(2) -47.7(4) N(2)-N(1)-C(5)-C(6) 58.9(3) C(1)-N(1)-C(5)-C(6) (3) N(2)-N(1)-C(5)-C(10) -59.8(3) C(1)-N(1)-C(5)-C(10) 100.8(3) N(1)-C(5)-C(6)-C(7) -61.7(4) C(10)-C(5)-C(6)-C(7) 57.2(4) C(5)-C(6)-C(7)-C(8) 5.6(4) N(1)-N(2)-C(8)-C(9) 57.7(4) C(11)-N(2)-C(8)-C(9) (3) N(1)-N(2)-C(8)-C(7) -62.6(3) C(11)-N(2)-C(8)-C(7) 85.1(4) C(6)-C(7)-C(8)-N(2) 53.8(4) C(6)-C(7)-C(8)-C(9) -63.8(4) N(2)-C(8)-C(9)-C(10) -62.3(4)

30 C(7)-C(8)-C(9)-C(10) 54.7(4) N(1)-C(5)-C(10)-C(9) 49.8(4) C(6)-C(5)-C(10)-C(9) -66.6(4) C(8)-C(9)-C(10)-C(5) 9.0(4) N(1)-N(2)-C(11)-C(12) 36.6(4) C(8)-N(2)-C(11)-C(12) (4) N(1)-N(2)-C(11)-C(20) (3) C(8)-N(2)-C(11)-C(20) 70.3(4) C(20)-C(11)-C(12)-C(13) 2.1(5) N(2)-C(11)-C(12)-C(13) (3) C(11)-C(12)-C(13)-C(14) 178.8(3) C(11)-C(12)-C(13)-C(18) -1.3(5) C(12)-C(13)-C(14)-C(15) (3) C(18)-C(13)-C(14)-C(15) 0.4(5) C(13)-C(14)-C(15)-C(16) 0.1(5) C(14)-C(15)-C(16)-C(17) -0.8(6) C(15)-C(16)-C(17)-C(18) 1.0(5) C(16)-C(17)-C(18)-C(19) 179.7(3) C(16)-C(17)-C(18)-C(13) -0.6(5) C(14)-C(13)-C(18)-C(17) -0.1(5) C(12)-C(13)-C(18)-C(17) 179.9(3) C(14)-C(13)-C(18)-C(19) 179.6(3) C(12)-C(13)-C(18)-C(19) -0.4(5) C(17)-C(18)-C(19)-C(20) (3) C(13)-C(18)-C(19)-C(20) 1.2(5) C(18)-C(19)-C(20)-C(11) -0.4(5) C(12)-C(11)-C(20)-C(19) -1.3(5) N(2)-C(11)-C(20)-C(19) 179.6(3) Symmetry transformations used to generate equivalent atoms: #1 -x,y,-z+1/2 #2 -x+1/2,-y+1/2,-z

31 Hy 15 2 NA 2+ (BF - 4 ) 2 (nel06) Data Collection A crystal with approximate dimensions 0.21 x 0.14 x 0.10 mm 3 was selected under oil under ambient conditions and attached to the tip of a glass capillary. The crystal was mounted in a stream of cold nitrogen at 100(2) K and centered in the X-ray beam by using a video camera. The crystal evaluation and data collection were performed on a Bruker CCD-1000 diffractometer with Mo K α (λ = Å) radiation and the diffractometer to crystal distance of 4.9 cm. The initial cell constants were obtained from three series of ω scans at different starting angles. Each series consisted of 20 frames collected at intervals of 0.3º in a 6º range about ω with the exposure time of 10 seconds per frame. A total of 44 reflections was obtained. The reflections were successfully indexed by an automated indexing routine built in the SMART program. The final cell constants were calculated from a set of strong reflections from the actual data collection. The data were collected by using the hemisphere data collection routine. The reciprocal space was surveyed to the extent of a full sphere to a resolution of 0.80 Å. A total of data were harvested by collecting three sets of frames with 0.3º scans in ω with an exposure time 70 sec per frame. These highly redundant datasets were corrected for Lorentz and polarization effects. The absorption correction was based on fitting a function to the empirical transmission surface as sampled by multiple equivalent measurements. 15 Structure Solution and Refinement The systematic absences in the diffraction data were uniquely consistent for the space group P2 1 /c that yielded chemically reasonable and computationally stable results of refinement. 16 A successful solution by the direct methods provided most non-hydrogen atoms from the E-map. The remaining non-hydrogen atoms were located in an alternating series of least-squares cycles and difference Fourier maps. All non-hydrogen atoms were refined with anisotropic displacement coefficients. All hydrogen atoms were included in the structure factor calculation at idealized positions and were allowed to ride on the neighboring atoms with relative isotropic displacement coefficients. The cation occupies a crystallographic inversion center.

32 The final least-squares refinement of 382 parameters against 4700 data resulted in residuals R (based on F 2 for I 2σ) and wr (based on F 2 for all data) of and , respectively. The final difference Fourier map was featureless. Table 1. Crystal data and structure refinement for nel06. Identification code nel06 Empirical formula C 78 H 84 B 2 N 4 Formula weight Temperature 100(2) K Wavelength Å Crystal system Monoclinic Space group P2 1 /c Unit cell dimensions a = (16) Å α= 90. b = (18) Å β= (2). c = (3) Å γ = 90. Volume (7) Å 3 Z 2 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 1180 Crystal size 0.21 x 0.14 x 0.10 mm 3 Theta range for data collection 2.14 to Index ranges -13<=h<=13, -15<=k<=15, -22<=l<=22 Reflections collected Independent reflections 4700 [R(int) = ] Completeness to theta = % Absorption correction Empirical with SADABS Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 4700 / 0 / 382 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Largest diff. peak and hole and e.å -3 Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for nel06. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. (nel06) x y z U(eq) N(1) 1911(2) 6568(2) 524(1) 25(1) N(2) 2040(2) 7511(2) 772(1) 20(1) B(1) 7594(3) 7247(2) 2565(2) 16(1) C(1) 456(2) 5335(2) -31(2) 17(1) C(2) 889(3) 5990(2) 548(2) 20(1) C(3) 428(3) 6011(2) 1134(2) 20(1) C(4) -477(2) 5348(2) 1177(2) 18(1) C(5) -893(2) 4683(2) 649(2) 18(1) C(6) 1162(3) 8339(2) 491(2) 27(1) C(7) 1791(3) 9154(3) 165(2) 33(1) C(8) 755(3) 8748(2) 1119(2) 27(1) C(9) 163(3) 7953(3) -70(2) 35(1)

33 C(10) 3230(3) 7760(2) 1153(2) 25(1) C(11) 3545(3) 6999(2) 1756(2) 28(1) C(12) 3527(3) 5938(3) 1438(2) 29(1) C(13) 3048(3) 6013(2) 651(2) 25(1) C(14) 3829(3) 6631(2) 287(2) 26(1) C(15) 4079(3) 7648(2) 666(2) 27(1) C(16) 7155(2) 8200(2) 2035(2) 17(1) C(17) 7576(3) 8370(2) 1428(2) 20(1) C(18) 7141(3) 9099(2) 935(2) 24(1) C(19) 6263(3) 9732(2) 1034(2) 28(1) C(20) 5841(3) 9621(2) 1640(2) 26(1) C(21) 6283(3) 8872(2) 2124(2) 21(1) C(22) 7155(2) 7418(2) 3302(2) 17(1) C(23) 6103(2) 7043(2) 3409(2) 17(1) C(24) 5726(3) 7197(2) 4022(2) 21(1) C(25) 6389(3) 7762(2) 4564(2) 21(1) C(26) 7413(3) 8172(2) 4475(2) 22(1) C(27) 7784(3) 8008(2) 3856(2) 20(1) C(28) 9022(3) 7163(2) 2752(1) 18(1) C(29) 9746(3) 8007(2) 2785(2) 21(1) C(30) 10949(3) 7945(2) 2971(2) 26(1) C(31) 11488(3) 7025(3) 3137(2) 29(1) C(32) 10813(3) 6166(3) 3110(2) 27(1) C(33) 9615(3) 6248(2) 2922(2) 22(1) C(34) 7053(2) 6191(2) 2169(2) 16(1) C(35) 6862(2) 5327(2) 2540(2) 19(1) C(36) 6435(3) 4434(2) 2209(2) 21(1) C(37) 6198(3) 4353(2) 1486(2) 20(1) C(38) 6395(2) 5180(2) 1100(2) 18(1) C(39) 6802(2) 6071(2) 1437(2) 16(1) Table 3. Bond lengths [Å] and angles [ ] for nel06.

34 N(1)-N(2) 1.342(3) N(1)-C(2) 1.444(4) N(1)-C(13) 1.507(4) N(2)-C(10) 1.476(4) N(2)-C(6) 1.530(4) B(1)-C(16) 1.645(4) B(1)-C(22) 1.650(4) B(1)-C(28) 1.653(4) B(1)-C(34) 1.662(4) C(1)-C(5)# (4) C(1)-C(2) 1.426(4) C(1)-C(1)# (6) C(2)-C(3) 1.374(4) C(3)-C(4) 1.406(4) C(4)-C(5) 1.363(4) C(5)-C(1)# (4) C(6)-C(9) 1.510(5) C(6)-C(8) 1.516(4) C(6)-C(7) 1.533(5) C(10)-C(11) 1.533(4) C(10)-C(15) 1.539(4) C(11)-C(12) 1.540(5) C(12)-C(13) 1.516(4) C(13)-C(14) 1.529(4) C(14)-C(15) 1.539(4) C(16)-C(17) 1.405(4) C(16)-C(21) 1.407(4) C(17)-C(18) 1.381(4) C(18)-C(19) 1.385(5) C(19)-C(20) 1.391(5) C(20)-C(21) 1.392(4) C(22)-C(23) 1.402(4) C(22)-C(27) 1.406(4) C(23)-C(24) 1.384(4) C(24)-C(25) 1.387(4) C(25)-C(26) 1.378(4) C(26)-C(27) 1.394(4) C(28)-C(29) 1.406(4) C(28)-C(33) 1.407(4) C(29)-C(30) 1.392(4) C(30)-C(31) 1.386(5) C(31)-C(32) 1.390(5) C(32)-C(33) 1.389(4) C(34)-C(39) 1.401(4) C(34)-C(35) 1.403(4) C(35)-C(36) 1.392(4) C(36)-C(37) 1.378(4) C(37)-C(38) 1.384(4) C(38)-C(39) 1.388(4) N(2)-N(1)-C(2) 120.9(2) N(2)-N(1)-C(13) 112.0(2) C(2)-N(1)-C(13) 117.4(2) N(1)-N(2)-C(10) 114.2(2) N(1)-N(2)-C(6) 122.2(2) C(10)-N(2)-C(6) 120.9(2)

35 C(16)-B(1)-C(22) 108.9(2) C(16)-B(1)-C(28) 110.7(2) C(22)-B(1)-C(28) 109.1(2) C(16)-B(1)-C(34) 109.0(2) C(22)-B(1)-C(34) 111.0(2) C(28)-B(1)-C(34) 108.2(2) C(5)#1-C(1)-C(2) 123.3(3) C(5)#1-C(1)-C(1)# (3) C(2)-C(1)-C(1)# (3) C(3)-C(2)-C(1) 122.1(3) C(3)-C(2)-N(1) 120.7(3) C(1)-C(2)-N(1) 117.0(3) C(2)-C(3)-C(4) 119.3(3) C(5)-C(4)-C(3) 120.9(3) C(4)-C(5)-C(1)# (3) C(9)-C(6)-C(8) 111.6(3) C(9)-C(6)-N(2) 111.9(3) C(8)-C(6)-N(2) 106.5(2) C(9)-C(6)-C(7) 108.4(3) C(8)-C(6)-C(7) 110.8(3) N(2)-C(6)-C(7) 107.6(3) N(2)-C(10)-C(11) 106.1(2) N(2)-C(10)-C(15) 110.6(2) C(11)-C(10)-C(15) 109.2(3) C(10)-C(11)-C(12) 108.6(3) C(13)-C(12)-C(11) 108.4(3) N(1)-C(13)-C(12) 108.4(2) N(1)-C(13)-C(14) 105.8(2) C(12)-C(13)-C(14) 112.2(3) C(13)-C(14)-C(15) 108.7(3) C(14)-C(15)-C(10) 107.5(3) C(17)-C(16)-C(21) 114.4(3) C(17)-C(16)-B(1) 122.2(3) C(21)-C(16)-B(1) 123.3(3) C(18)-C(17)-C(16) 123.5(3) C(17)-C(18)-C(19) 120.3(3) C(18)-C(19)-C(20) 118.6(3) C(19)-C(20)-C(21) 120.0(3) C(20)-C(21)-C(16) 123.1(3) C(23)-C(22)-C(27) 114.7(3) C(23)-C(22)-B(1) 123.2(3) C(27)-C(22)-B(1) 122.0(3) C(24)-C(23)-C(22) 123.3(3) C(23)-C(24)-C(25) 120.0(3) C(26)-C(25)-C(24) 118.9(3) C(25)-C(26)-C(27) 120.4(3) C(26)-C(27)-C(22) 122.5(3) C(29)-C(28)-C(33) 114.4(3) C(29)-C(28)-B(1) 122.7(3) C(33)-C(28)-B(1) 122.8(3) C(30)-C(29)-C(28) 122.9(3) C(31)-C(30)-C(29) 120.3(3) C(30)-C(31)-C(32) 119.1(3) C(33)-C(32)-C(31) 119.4(3) C(32)-C(33)-C(28) 123.9(3) C(39)-C(34)-C(35) 114.3(3)

36 C(39)-C(34)-B(1) 122.8(2) C(35)-C(34)-B(1) 122.9(2) C(36)-C(35)-C(34) 123.0(3) C(37)-C(36)-C(35) 120.7(3) C(36)-C(37)-C(38) 118.3(3) C(37)-C(38)-C(39) 120.3(3) C(38)-C(39)-C(34) 123.5(3) Symmetry transformations used to generate equivalent atoms: #1 -x,-y+1,-z Table 4. Anisotropic displacement parameters (Å 2 x 10 3 ) for nel06. The anisotropic displacement factor exponent takes the form: -2π 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 N(1) 33(2) 22(1) 22(1) -4(1) 11(1) -8(1) N(2) 20(1) 20(1) 20(1) -8(1) 6(1) -3(1) B(1) 20(2) 16(2) 12(2) 0(1) 3(1) -2(1) C(1) 21(2) 17(2) 15(2) 2(1) 7(1) 5(1) C(2) 24(2) 16(2) 21(2) -1(1) 7(1) -5(1) C(3) 26(2) 18(2) 17(2) -3(1) 6(1) -1(1) C(4) 21(2) 22(2) 12(2) -1(1) 7(1) 1(1) C(5) 16(2) 19(2) 18(2) 3(1) 5(1) -2(1) C(6) 30(2) 23(2) 27(2) 2(1) 5(1) 2(1) C(7) 40(2) 27(2) 33(2) 8(2) 8(2) 1(2) C(8) 26(2) 22(2) 30(2) -1(1) 2(1) 5(1) C(9) 43(2) 26(2) 31(2) 6(2) 0(2) -3(2) C(10) 25(2) 26(2) 21(2) -3(1) 2(1) -4(1) C(11) 30(2) 30(2) 24(2) 1(1) 4(1) 2(2) C(12) 26(2) 33(2) 31(2) 4(2) 9(2) 1(2) C(13) 20(2) 23(2) 33(2) -7(1) 7(1) 3(1) C(14) 23(2) 31(2) 24(2) -3(1) 5(1) 1(1) C(15) 24(2) 29(2) 29(2) -1(1) 6(1) -4(1) C(16) 21(2) 14(2) 16(2) -4(1) 2(1) -6(1) C(17) 23(2) 13(2) 23(2) -3(1) 3(1) -4(1) C(18) 33(2) 19(2) 20(2) 1(1) 7(1) -8(1) C(19) 41(2) 18(2) 23(2) 6(1) -1(2) -1(2) C(20) 32(2) 17(2) 25(2) -1(1) 1(1) 6(1) C(21) 26(2) 19(2) 19(2) -4(1) 3(1) -2(1) C(22) 19(2) 15(2) 16(2) 2(1) 2(1) 4(1) C(23) 20(2) 16(2) 14(2) 0(1) -1(1) 3(1) C(24) 20(2) 20(2) 23(2) 4(1) 7(1) 4(1) C(25) 25(2) 25(2) 15(2) 1(1) 6(1) 7(1) C(26) 27(2) 20(2) 16(2) -6(1) 1(1) 3(1) C(27) 18(2) 21(2) 20(2) -1(1) 4(1) 1(1) C(28) 24(2) 22(2) 8(1) -1(1) 7(1) 1(1) C(29) 25(2) 21(2) 19(2) -3(1) 7(1) -2(1) C(30) 24(2) 31(2) 25(2) -4(1) 10(1) -8(1) C(31) 16(2) 44(2) 27(2) -2(2) 6(1) 2(2) C(32) 23(2) 29(2) 28(2) 1(1) 5(1) 8(1) C(33) 25(2) 21(2) 20(2) 1(1) 6(1) -1(1) C(34) 14(1) 17(2) 17(2) 0(1) 4(1) 4(1) C(35) 22(2) 18(2) 17(2) 2(1) 4(1) 3(1) C(36) 25(2) 16(2) 24(2) 3(1) 7(1) 0(1) C(37) 19(2) 14(2) 26(2) -5(1) 5(1) 1(1)