Table 1 Identification code marc002 Empirical formula C20 H17 Br O4 Formula weight 401.24 Temperature 200(2) K Wavelength 1.54178 A Crystal system, space group Monoclinic, P2(1) Unit cell dimensions a = 6.8349(3) A alpha = 90 deg. b = 7.3672(3) A beta = 100.593(2) deg. c = 18.3255(8) A gamma = 90 deg. Volume 907.04(7) A^3 Z, Calculated density 2, 1.469 Mg/m^3 Absorption coefficient 3.269 mm^-1 F(000) 408 Crystal size 0.453 x 0.371 x 0.086 mm Theta range for data collection 2.453 to 74.779 deg. Limiting indices -8<=h<=8, -9<=k<=9, -22<=l<=22 Reflections collected / unique 19560 / 3698 [R(int) = 0.0685] Completeness to theta = 67.679 99.8 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.7538 and 0.4614 Refinement method Full-matrix least-squares on F^2 Data / restraints / parameters 3698 / 1 / 232 Goodness-of-fit on F^2 1.114 Final R indices [I>2sigma(I)] R1 = 0.0441, wR2 = 0.1201 R indices (all data) R1 = 0.0455, wR2 = 0.1214 Absolute structure parameter -0.01(3) Extinction coefficient 0.0098(15) Largest diff. peak and hole 0.634 and -0.412 e.A^-3 Table 2 displacement parameters (A^2 x 10^3) for marc002. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. ________________________________________________________________ x y z U(eq) ________________________________________________________________ C(1) 6532(6) 4414(6) 3727(2) 27(1) C(2) 6327(6) 5490(7) 4422(3) 31(1) C(3) 7719(6) 7007(7) 4489(3) 32(1) C(4) 8755(6) 7012(6) 3940(3) 30(1) C(5) 8057(6) 5548(6) 3372(2) 27(1) C(6) 4501(6) 4208(5) 3231(2) 28(1) C(7) 2662(8) 3247(8) 1448(3) 44(1) C(8) 970(10) 2723(11) 937(4) 59(2) C(9) -472(10) 1670(9) 1173(4) 60(2) C(10) -262(9) 1152(8) 1898(4) 53(1) C(11) 1402(8) 1658(7) 2409(3) 43(1) C(12) 2838(6) 2695(6) 2160(3) 32(1) C(13) 7362(7) 2524(7) 3963(3) 36(1) C(14) 10427(7) 8248(7) 3861(3) 40(1) C(15) 8098(7) 5961(7) 2007(3) 32(1) C(16) 7352(7) 6672(7) 1312(3) 37(1) C(17) 5735(8) 7821(7) 1230(3) 37(1) C(18) 4866(8) 8301(7) 1825(3) 39(1) C(19) 5658(7) 7619(7) 2520(3) 35(1) C(20) 7246(6) 6391(6) 2618(3) 29(1) O(1) 2980(5) 4896(6) 3333(2) 44(1) O(2) 4621(4) 3107(5) 2656(2) 34(1) O(3) 5286(5) 5081(6) 4871(2) 44(1) O(4) 8048(5) 8140(6) 5088(2) 44(1) Br(1) 4664(1) 8809(1) 282(1) 55(1) ________________________________________________________________ Table 3 _____________________________________________________________ C(1)-C(6) 1.520(6) C(1)-C(2) 1.527(6) C(1)-C(13) 1.536(6) C(1)-C(5) 1.568(5) C(2)-O(3) 1.222(5) C(2)-C(3) 1.458(7) C(3)-C(4) 1.332(6) C(3)-O(4) 1.365(6) C(4)-C(14) 1.489(6) C(4)-C(5) 1.514(6) C(5)-C(20) 1.523(6) C(5)-H(5) 1.0000 C(6)-O(1) 1.202(5) C(6)-O(2) 1.344(5) C(7)-C(12) 1.351(7) C(7)-C(8) 1.402(8) C(7)-H(7) 0.9500 C(8)-C(9) 1.385(11) C(8)-H(8) 0.9500 C(9)-C(10) 1.364(10) C(9)-H(9) 0.9500 C(10)-C(11) 1.385(8) C(10)-H(10) 0.9500 C(11)-C(12) 1.386(7) C(11)-H(11) 0.9500 C(12)-O(2) 1.413(5) C(13)-H(13A) 0.9800 C(13)-H(13B) 0.9800 C(13)-H(13C) 0.9800 C(14)-H(14A) 0.9800 C(14)-H(14B) 0.9800 C(14)-H(14C) 0.9800 C(15)-C(16) 1.385(7) C(15)-C(20) 1.391(6) C(15)-H(15) 0.9500 C(16)-C(17) 1.378(7) C(16)-H(16) 0.9500 C(17)-C(18) 1.381(7) C(17)-Br(1) 1.902(5) C(18)-C(19) 1.382(7) C(18)-H(18) 0.9500 C(19)-C(20) 1.399(6) C(19)-H(19) 0.9500 O(4)-H(4) 0.77(8) C(6)-C(1)-C(2) 109.7(3) C(6)-C(1)-C(13) 109.1(4) C(2)-C(1)-C(13) 108.8(4) C(6)-C(1)-C(5) 114.1(4) C(2)-C(1)-C(5) 103.9(3) C(13)-C(1)-C(5) 111.1(3) O(3)-C(2)-C(3) 125.7(5) O(3)-C(2)-C(1) 126.0(5) C(3)-C(2)-C(1) 108.0(3) C(4)-C(3)-O(4) 125.1(4) C(4)-C(3)-C(2) 111.6(4) O(4)-C(3)-C(2) 123.0(4) C(3)-C(4)-C(14) 126.8(4) C(3)-C(4)-C(5) 111.9(4) C(14)-C(4)-C(5) 121.3(4) C(4)-C(5)-C(20) 110.5(4) C(4)-C(5)-C(1) 104.1(3) C(20)-C(5)-C(1) 115.8(3) C(4)-C(5)-H(5) 108.8 C(20)-C(5)-H(5) 108.8 C(1)-C(5)-H(5) 108.8 O(1)-C(6)-O(2) 123.8(4) O(1)-C(6)-C(1) 125.8(4) O(2)-C(6)-C(1) 110.4(3) C(12)-C(7)-C(8) 118.6(5) C(12)-C(7)-H(7) 120.7 C(8)-C(7)-H(7) 120.7 C(9)-C(8)-C(7) 119.5(6) C(9)-C(8)-H(8) 120.3 C(7)-C(8)-H(8) 120.3 C(10)-C(9)-C(8) 120.5(6) C(10)-C(9)-H(9) 119.7 C(8)-C(9)-H(9) 119.7 C(9)-C(10)-C(11) 120.7(6) C(9)-C(10)-H(10) 119.7 C(11)-C(10)-H(10) 119.7 C(10)-C(11)-C(12) 117.9(6) C(10)-C(11)-H(11) 121.0 C(12)-C(11)-H(11) 121.0 C(7)-C(12)-C(11) 122.8(5) C(7)-C(12)-O(2) 118.0(4) C(11)-C(12)-O(2) 119.0(5) C(1)-C(13)-H(13A) 109.5 C(1)-C(13)-H(13B) 109.5 H(13A)-C(13)-H(13B) 109.5 C(1)-C(13)-H(13C) 109.5 H(13A)-C(13)-H(13C) 109.5 H(13B)-C(13)-H(13C) 109.5 C(4)-C(14)-H(14A) 109.5 C(4)-C(14)-H(14B) 109.5 H(14A)-C(14)-H(14B) 109.5 C(4)-C(14)-H(14C) 109.5 H(14A)-C(14)-H(14C) 109.5 H(14B)-C(14)-H(14C) 109.5 C(16)-C(15)-C(20) 121.1(4) C(16)-C(15)-H(15) 119.5 C(20)-C(15)-H(15) 119.5 C(17)-C(16)-C(15) 119.0(4) C(17)-C(16)-H(16) 120.5 C(15)-C(16)-H(16) 120.5 C(16)-C(17)-C(18) 121.6(5) C(16)-C(17)-Br(1) 120.0(4) C(18)-C(17)-Br(1) 118.3(4) C(17)-C(18)-C(19) 118.8(5) C(17)-C(18)-H(18) 120.6 C(19)-C(18)-H(18) 120.6 C(18)-C(19)-C(20) 121.1(4) C(18)-C(19)-H(19) 119.4 C(20)-C(19)-H(19) 119.4 C(15)-C(20)-C(19) 118.3(4) C(15)-C(20)-C(5) 120.1(4) C(19)-C(20)-C(5) 121.7(4) C(6)-O(2)-C(12) 117.7(3) C(3)-O(4)-H(4) 111(6) _____________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 4 The anisotropic displacement factor exponent takes the form: -2 pi^2 [ h^2 a*^2 U11 + ... + 2 h k a* b* U12 ] _______________________________________________________________________ U11 U22 U33 U23 U13 U12 _______________________________________________________________________ C(1) 21(2) 31(2) 30(2) -2(2) 7(2) 3(2) C(2) 21(2) 42(2) 30(2) -4(2) 4(2) 1(2) C(3) 23(2) 38(2) 34(2) -8(2) 1(2) 4(2) C(4) 23(2) 32(2) 32(2) -3(2) 2(2) 4(2) C(5) 20(2) 30(2) 31(2) -4(2) 6(1) -1(2) C(6) 23(2) 29(2) 31(2) -3(2) 6(2) 0(1) C(7) 42(3) 52(3) 37(3) -6(2) 6(2) -3(2) C(8) 62(4) 70(4) 40(3) -10(3) -6(3) -1(3) C(9) 48(3) 55(4) 70(4) -16(3) -11(3) -6(3) C(10) 40(3) 44(3) 68(4) -6(3) -6(2) -11(2) C(11) 41(3) 36(2) 49(3) 0(2) 2(2) -10(2) C(12) 26(2) 32(2) 38(2) -7(2) 3(2) 0(2) C(13) 31(2) 33(2) 44(3) 7(2) 4(2) 5(2) C(14) 32(2) 40(2) 47(3) -6(2) 8(2) -8(2) C(15) 32(2) 32(2) 34(2) -4(2) 9(2) 3(2) C(16) 40(2) 37(2) 33(2) -2(2) 8(2) -2(2) C(17) 44(3) 33(2) 31(2) -1(2) -2(2) -6(2) C(18) 36(2) 34(2) 44(3) 2(2) 2(2) 5(2) C(19) 34(2) 36(2) 36(2) -2(2) 8(2) 6(2) C(20) 24(2) 29(2) 32(2) 0(2) 4(2) 1(2) O(1) 22(1) 57(2) 51(2) -16(2) 4(1) 6(2) O(2) 23(1) 41(2) 36(2) -10(1) 3(1) 2(1) O(3) 37(2) 63(2) 34(2) -6(2) 14(1) -8(2) O(4) 28(2) 60(2) 42(2) -23(2) 3(1) 1(2) Br(1) 75(1) 46(1) 36(1) 6(1) -8(1) 5(1) _______________________________________________________________________ Table 5 displacement parameters (A^2 x 10^3) for marc002. ________________________________________________________________ x y z U(eq) ________________________________________________________________ H(5) 9214 4755 3325 32 H(7) 3664 3974 1297 53 H(8) 813 3088 432 71 H(9) -1615 1304 827 72 H(10) -1267 438 2053 63 H(11) 1554 1306 2915 51 H(13A) 6446 1894 4231 54 H(13B) 8665 2648 4288 54 H(13C) 7504 1822 3522 54 H(14A) 10351 9348 4156 59 H(14B) 10334 8578 3338 59 H(14C) 11696 7633 4039 59 H(15) 9211 5166 2067 39 H(16) 7945 6372 897 44 H(18) 3745 9086 1759 46 H(19) 5114 7990 2937 42 H(4) 7070(120) 8530(120) 5170(40) 65 ________________________________________________________________ Table 6 ________________________________________________________________ C(6)-C(1)-C(2)-O(3) 58.3(6) C(13)-C(1)-C(2)-O(3) -60.9(6) C(5)-C(1)-C(2)-O(3) -179.4(5) C(6)-C(1)-C(2)-C(3) -126.5(4) C(13)-C(1)-C(2)-C(3) 114.3(4) C(5)-C(1)-C(2)-C(3) -4.2(5) O(3)-C(2)-C(3)-C(4) 174.9(5) C(1)-C(2)-C(3)-C(4) -0.3(5) O(3)-C(2)-C(3)-O(4) 1.6(8) C(1)-C(2)-C(3)-O(4) -173.7(4) O(4)-C(3)-C(4)-C(14) -1.1(8) C(2)-C(3)-C(4)-C(14) -174.2(4) O(4)-C(3)-C(4)-C(5) 178.2(4) C(2)-C(3)-C(4)-C(5) 5.1(6) C(3)-C(4)-C(5)-C(20) 117.4(4) C(14)-C(4)-C(5)-C(20) -63.2(5) C(3)-C(4)-C(5)-C(1) -7.5(5) C(14)-C(4)-C(5)-C(1) 171.9(4) C(6)-C(1)-C(5)-C(4) 126.0(4) C(2)-C(1)-C(5)-C(4) 6.7(4) C(13)-C(1)-C(5)-C(4) -110.1(4) C(6)-C(1)-C(5)-C(20) 4.6(5) C(2)-C(1)-C(5)-C(20) -114.8(4) C(13)-C(1)-C(5)-C(20) 128.4(4) C(2)-C(1)-C(6)-O(1) 5.3(6) C(13)-C(1)-C(6)-O(1) 124.4(5) C(5)-C(1)-C(6)-O(1) -110.7(5) C(2)-C(1)-C(6)-O(2) -173.6(4) C(13)-C(1)-C(6)-O(2) -54.6(4) C(5)-C(1)-C(6)-O(2) 70.4(4) C(12)-C(7)-C(8)-C(9) 0.3(9) C(7)-C(8)-C(9)-C(10) 0.5(10) C(8)-C(9)-C(10)-C(11) -0.5(10) C(9)-C(10)-C(11)-C(12) -0.2(9) C(8)-C(7)-C(12)-C(11) -1.1(8) C(8)-C(7)-C(12)-O(2) 175.0(5) C(10)-C(11)-C(12)-C(7) 1.0(8) C(10)-C(11)-C(12)-O(2) -175.0(5) C(20)-C(15)-C(16)-C(17) -0.1(7) C(15)-C(16)-C(17)-C(18) 1.1(7) C(15)-C(16)-C(17)-Br(1) -179.6(4) C(16)-C(17)-C(18)-C(19) 0.6(8) Br(1)-C(17)-C(18)-C(19) -178.8(4) C(17)-C(18)-C(19)-C(20) -3.2(8) C(16)-C(15)-C(20)-C(19) -2.4(7) C(16)-C(15)-C(20)-C(5) 178.2(4) C(18)-C(19)-C(20)-C(15) 4.1(7) C(18)-C(19)-C(20)-C(5) -176.6(4) C(4)-C(5)-C(20)-C(15) 120.8(4) C(1)-C(5)-C(20)-C(15) -121.3(4) C(4)-C(5)-C(20)-C(19) -58.5(5) C(1)-C(5)-C(20)-C(19) 59.4(5) O(1)-C(6)-O(2)-C(12) -2.1(7) C(1)-C(6)-O(2)-C(12) 176.8(4) C(7)-C(12)-O(2)-C(6) 116.6(5) C(11)-C(12)-O(2)-C(6) -67.2(6) ________________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 7 ____________________________________________________________________________ D-H...A d(D-H) d(H...A) d(D...A) <(DHA) O(4)-H(4)...O(3)#1 0.77(8) 1.96(8) 2.703(5) 162(8) ____________________________________________________________________________ Symmetry transformations used to generate equivalent atoms: #1 -x+1,y+1/2,-z+1