Table 1. Crystal data and structure refinement for Compound 6a. Identification code 170OHA11 (Solved by: R. A. Toscano) Project Title Compound 6a Empirical formula C20 H19 Br O7 Formula weight 451.26 Temperature 298(2) K Wavelength 0.71073 Å Crystal system Orthorhombic Space group P 21 21 21 Unit cell dimensions a = 7.503(1) Å a= 90° b = 8.168(2) Å ß= 90° c = 31.10(1) Å . = 90° Volume 1906.2(6) Å3 Z 4 Density (calculated) 1.572 Mg/m3 Absorption coefficient 2.197 mm-1 F(000) 920 Crystal size / color / shape 0.458 x 0.092 x 0.062 mm / colorless / prism Theta range for data collection 2.58 to 25.34° Index ranges -8= h =9, -9= k =9, -37= l =37 Reflections collected 13237 Independent reflections 3473 [R(int) = 0.0735] Completeness to theta = 25.34° 99.8 % Measurement device Bruker Smart Apex CCD diffractometer 01-670 Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.8751 and 0.5612 Refinement method Full-matrix least-squares on F2 Data / restraints / parameters 3473 / 1 / 257 Goodness-of-fit on F2 1.018 Final R indices [I>2s(I)] R1 = 0.0579, wR2 = 0.1381 R indices (all data) R1 = 0.1120, wR2 = 0.1636 Absolute structure parameter 0.02(2) Largest diff. peak and hole 0.661 and -0.377 e.Å-3 Table 2. Atomic coordinates ( x 104) and equivalent isotropic displacement parameters (Å2x 103) for Compound 6a. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. x y z U(eq) Br(1) 3234(1) 5081(1) 4460(1) 83(1) O(1) 6467(6) 5177(6) 6158(1) 57(1) O(2) 3873(8) 627(7) 6769(2) 72(2) O(3) 1367(7) 2550(6) 5662(2) 64(1) O(4) -262(7) 5929(7) 4623(2) 74(2) O(5) 1704(8) 314(7) 6052(2) 80(2) O(6) 9059(9) 3861(8) 7719(2) 92(2) O(7) 6246(8) 3028(6) 7577(2) 68(2) C(1) 5799(9) 6538(8) 6412(2) 49(2) C(2) 7203(10) 7325(9) 6681(2) 56(2) C(3) 7973(10) 6230(10) 6999(2) 59(2) C(4) 7492(9) 4704(8) 7068(2) 49(2) C(5) 5963(9) 3869(8) 6846(2) 43(2) C(6) 6514(11) 2174(8) 6650(2) 54(2) C(7) 4939(10) 1322(8) 6441(2) 52(2) C(8) 3946(9) 2391(7) 6129(2) 45(2) C(9) 3426(9) 4175(8) 6288(2) 48(2) C(10) 5131(7) 4878(9) 6489(2) 42(1) C(11) 2818(9) 5168(10) 5882(2) 63(2) C(12) 2220(10) 4046(9) 5507(2) 60(2) C(13) 941(9) 4825(11) 5212(2) 61(2) C(14) -926(10) 5205(13) 5290(3) 77(2) C(15) -1590(12) 5853(12) 4928(3) 82(3) C(16) 1226(9) 5274(10) 4806(2) 60(2) C(17) 2274(10) 1649(9) 5944(2) 57(2) C(18) 7784(13) 3868(10) 7475(3) 71(3) C(19) 4932(10) 3502(8) 7267(2) 49(2) C(20) 1919(10) 4169(10) 6611(2) 63(2) Table 3. Bond lengths [Å] and angles [°] for Compound 6a. Br(1)-C(16) 1.857(7) C(4)-C(5) 1.503(9) O(1)-C(1) 1.453(8) C(5)-C(10) 1.517(9) O(1)-C(10) 1.458(6) C(5)-C(19) 1.550(9) O(2)-C(7) 1.415(9) C(5)-C(6) 1.568(9) O(3)-C(17) 1.332(9) C(6)-C(7) 1.518(10) O(3)-C(12) 1.461(9) C(7)-C(8) 1.504(9) O(4)-C(16) 1.362(8) C(8)-C(17) 1.507(10) O(4)-C(15) 1.379(10) C(8)-C(9) 1.587(9) O(5)-C(17) 1.219(8) C(9)-C(20) 1.512(9) O(6)-C(18) 1.221(9) C(9)-C(10) 1.535(9) O(7)-C(18) 1.380(11) C(9)-C(11) 1.567(9) O(7)-C(19) 1.434(8) C(11)-C(12) 1.550(10) C(1)-C(10) 1.465(10) C(12)-C(13) 1.472(10) C(1)-C(2) 1.492(9) C(13)-C(16) 1.334(10) C(2)-C(3) 1.453(10) C(13)-C(14) 1.455(11) C(3)-C(4) 1.315(11) C(14)-C(15) 1.339(11) C(4)-C(18) 1.456(10) C(1)-O(1)-C(10) 60.4(4) C(10)-C(5)-C(6) 107.7(5) C(17)-O(3)-C(12) 117.1(6) C(19)-C(5)-C(6) 106.8(5) C(16)-O(4)-C(15) 106.6(6) C(7)-C(6)-C(5) 111.5(6) C(18)-O(7)-C(19) 106.6(5) O(2)-C(7)-C(8) 114.7(6) O(1)-C(1)-C(10) 59.9(4) O(2)-C(7)-C(6) 108.4(6) O(1)-C(1)-C(2) 113.0(6) C(8)-C(7)-C(6) 113.3(6) C(10)-C(1)-C(2) 123.2(6) C(7)-C(8)-C(17) 115.2(6) C(3)-C(2)-C(1) 113.5(6) C(7)-C(8)-C(9) 117.0(5) C(4)-C(3)-C(2) 125.8(7) C(17)-C(8)-C(9) 106.5(5) C(3)-C(4)-C(18) 123.0(7) C(20)-C(9)-C(10) 110.8(5) C(3)-C(4)-C(5) 124.4(6) C(20)-C(9)-C(11) 108.5(6) C(18)-C(4)-C(5) 107.6(6) C(10)-C(9)-C(11) 112.1(5) C(4)-C(5)-C(10) 113.8(5) C(20)-C(9)-C(8) 112.8(6) C(4)-C(5)-C(19) 94.6(5) C(10)-C(9)-C(8) 105.4(5) C(10)-C(5)-C(19) 121.2(5) C(11)-C(9)-C(8) 107.2(5) C(4)-C(5)-C(6) 112.2(6) O(1)-C(10)-C(1) 59.6(4) O(1)-C(10)-C(5) 109.0(5) C(15)-C(14)-C(13) 107.6(7) C(1)-C(10)-C(5) 118.8(5) C(14)-C(15)-O(4) 109.2(7) O(1)-C(10)-C(9) 110.4(4) C(13)-C(16)-O(4) 111.9(6) C(1)-C(10)-C(9) 124.4(6) C(13)-C(16)-Br(1) 130.9(6) C(5)-C(10)-C(9) 115.9(6) O(4)-C(16)-Br(1) 117.1(5) C(12)-C(11)-C(9) 112.6(6) O(5)-C(17)-O(3) 119.9(7) O(3)-C(12)-C(13) 106.3(6) O(5)-C(17)-C(8) 123.1(7) O(3)-C(12)-C(11) 111.9(6) O(3)-C(17)-C(8) 117.0(6) C(13)-C(12)-C(11) 113.7(6) O(6)-C(18)-O(7) 120.7(8) C(16)-C(13)-C(14) 104.7(7) O(6)-C(18)-C(4) 131.3(10) C(16)-C(13)-C(12) 127.2(7) O(7)-C(18)-C(4) 107.9(7) C(14)-C(13)-C(12) 128.1(7) O(7)-C(19)-C(5) 106.1(6) Table 4. Anisotropic displacement parameters (Å2x 103)for Compound 6a. The anisotropic displacement factor exponent takes the form: -2p2[ h2a*2U11 + ... + 2 h k a* b* U12] U11 U22 U33 U23 U13 U12 Br(1) 70(1) 120(1) 59(1) -5(1) 5(1) 18(1) O(1) 56(3) 56(3) 59(2) 2(3) 15(2) -2(3) O(2) 87(4) 70(4) 60(3) 15(3) -1(3) -18(3) O(3) 63(3) 73(3) 57(3) -1(3) -10(3) -15(3) O(4) 60(3) 108(4) 53(3) -6(3) -7(3) 22(3) O(5) 94(4) 58(3) 89(4) 5(3) -19(3) -32(4) O(6) 85(4) 85(4) 106(5) -9(4) -39(4) 30(4) O(7) 91(4) 62(3) 51(3) -4(2) -15(3) 7(3) C(1) 54(4) 34(4) 59(4) -3(3) -10(4) -2(3) C(2) 52(5) 47(4) 70(5) 4(4) 6(4) -16(4) C(3) 37(4) 74(6) 64(5) -13(4) -4(4) 2(4) C(4) 46(3) 38(4) 64(4) -17(4) -7(3) 10(3) C(5) 47(4) 42(4) 40(4) -5(3) -1(3) 1(3) C(6) 64(5) 40(4) 57(4) -11(3) 7(4) 8(4) C(7) 65(5) 43(4) 46(4) 6(3) 6(4) 1(4) C(8) 53(4) 36(4) 48(4) -5(3) 8(3) -5(3) C(9) 45(4) 43(4) 56(4) -7(3) -2(4) -6(3) C(10) 41(3) 46(4) 39(3) -1(4) 10(3) 1(4) C(11) 61(4) 53(4) 75(4) 8(4) -13(4) 11(4) C(12) 61(5) 61(4) 58(4) 4(4) 3(4) -4(4) C(13) 56(4) 76(5) 51(4) -7(5) -1(3) 4(5) C(14) 60(5) 103(7) 67(5) -9(6) 9(4) 14(6) C(15) 55(5) 122(7) 69(5) -15(5) -12(5) 25(5) C(16) 51(4) 74(5) 56(4) -3(4) -9(3) 14(4) C(17) 58(5) 53(5) 59(5) -14(4) 0(4) -9(4) C(18) 79(7) 53(5) 82(6) -20(5) -36(5) 29(5) C(19) 60(5) 44(4) 42(4) -3(3) 6(4) -8(4) C(20) 50(4) 71(5) 67(5) -19(4) 10(4) 5(4) Table 5. Hydrogen coordinates ( x 104) and isotropic displacement parameters (Å2x 103) for Compound 6a. x y z U(eq) H(2) 2770(30) 580(120) 6710(30) 109 H(1) 4980 7285 6264 59 H(2A) 8145 7724 6495 68 H(2B) 6690 8261 6828 68 H(3) 8887 6646 7169 70 H(6A) 7443 2339 6438 64 H(6B) 6992 1482 6876 64 H(7) 5426 407 6274 62 H(8) 4752 2550 5885 55 H(11A) 1838 5880 5962 76 H(11B) 3796 5852 5786 76 H(12) 3280 3737 5342 72 H(14) -1546 5029 5545 92 H(15) -2760 6198 4890 98 H(19A) 4294 4468 7363 58 H(19B) 4080 2625 7222 58 H(20A) 1996 5128 6788 94 H(20B) 2004 3209 6788 94 H(20C) 799 4165 6461 94 Table 6. Hydrogen bonds for Compound 6a [Å and °]. D-H...A d(D-H) d(H...A) d(D...A) <(DHA) O(2)-H(2)...O(5) 0.850(5) 2.20(8) 2.771(8) 124(8) O(2)-H(2)...O(6)#1 0.850(5) 2.65(9) 3.076(9) 112(8) Symmetry transformations used to generate equivalent atoms: #1 -x+1,y-1/2,-z+3/2