Table 1. Crystal data and structure refinement for marc. Identification code marc Empirical formula C17 H20 O4 Formula weight 288.33 Temperature 200(2) K Wavelength 0.71073 A Crystal system, space group Monoclinic, C 2/c Unit cell dimensions a = 24.445(7) A alpha = 90 deg. b = 7.241(2) A beta = 101.424(4) deg. c = 17.657(5) A gamma = 90 deg. Volume 3063.3(16) A^3 Z, Calculated density 8, 1.250 Mg/m^3 Absorption coefficient 0.088 mm^-1 F(000) 1232 Crystal size 0.600 x 0.557 x 0.440 mm Theta range for data collection 2.354 to 27.650 deg. Limiting indices -29<=h<=31, -9<=k<=9, -22<=l<=23 Reflections collected / unique 9710 / 3528 [R(int) = 0.0254] Completeness to theta = 25.000 99.3 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.7456 and 0.6892 Refinement method Full-matrix least-squares on F^2 Data / restraints / parameters 3528 / 0 / 194 Goodness-of-fit on F^2 1.039 Final R indices [I>2sigma(I)] R1 = 0.0451, wR2 = 0.1208 R indices (all data) R1 = 0.0551, wR2 = 0.1283 Extinction coefficient n/a Largest diff. peak and hole 0.343 and -0.276 e.A^-3 Table 2. Atomic coordinates ( x 10^4) and equivalent isotropic displacement parameters (A^2 x 10^3) for marc. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. ________________________________________________________________ x y z U(eq) ________________________________________________________________ O(1) 2031(1) 5587(2) 9153(1) 37(1) O(2) 1149(1) 5566(1) 8481(1) 26(1) O(3) 649(1) 5154(1) 10008(1) 32(1) O(4) -226(1) 7705(1) 9276(1) 30(1) C(1) 1212(1) 9341(2) 9314(1) 20(1) C(2) 1322(1) 7292(2) 9646(1) 20(1) C(3) 741(1) 6597(2) 9694(1) 21(1) C(4) 331(1) 7946(2) 9338(1) 21(1) C(5) 577(1) 9445(2) 9108(1) 22(1) C(6) 1194(1) 9356(2) 7859(1) 29(1) C(7) 1450(1) 9573(2) 7229(1) 39(1) C(8) 2002(1) 10118(3) 7338(1) 44(1) C(9) 2295(1) 10436(3) 8079(1) 43(1) C(10) 2040(1) 10221(2) 8712(1) 32(1) C(11) 1484(1) 9669(2) 8611(1) 23(1) C(12) 1410(1) 10817(2) 9937(1) 30(1) C(13) 1551(1) 6055(2) 9077(1) 22(1) C(14) 1330(1) 4626(2) 7844(1) 35(1) C(15) 835(1) 4470(3) 7195(1) 46(1) C(16) 1707(1) 7121(2) 10440(1) 31(1) C(17) 268(1) 11130(2) 8762(1) 33(1) ________________________________________________________________ Table 3. Bond lengths [A] and angles [deg] for marc. _____________________________________________________________ O(1)-C(13) 1.2024(17) O(2)-C(13) 1.3384(16) O(2)-C(14) 1.4571(18) O(3)-C(3) 1.2237(17) O(4)-C(4) 1.3553(16) O(4)-H(4A) 0.8400 C(1)-C(5) 1.5235(18) C(1)-C(11) 1.5381(18) C(1)-C(12) 1.5419(19) C(1)-C(2) 1.5987(18) C(2)-C(3) 1.5255(17) C(2)-C(16) 1.5301(18) C(2)-C(13) 1.5328(19) C(3)-C(4) 1.4500(18) C(4)-C(5) 1.3427(18) C(5)-C(17) 1.4995(19) C(6)-C(7) 1.390(2) C(6)-C(11) 1.393(2) C(6)-H(6A) 0.9500 C(7)-C(8) 1.381(3) C(7)-H(7A) 0.9500 C(8)-C(9) 1.382(3) C(8)-H(8A) 0.9500 C(9)-C(10) 1.391(2) C(9)-H(9A) 0.9500 C(10)-C(11) 1.394(2) C(10)-H(10) 0.9500 C(12)-H(12A) 0.9800 C(12)-H(12B) 0.9800 C(12)-H(12C) 0.9800 C(14)-C(15) 1.497(2) C(14)-H(14A) 0.9900 C(14)-H(14B) 0.9900 C(15)-H(15A) 0.9800 C(15)-H(15B) 0.9800 C(15)-H(15C) 0.9800 C(16)-H(16A) 0.9800 C(16)-H(16B) 0.9800 C(16)-H(16C) 0.9800 C(17)-H(17A) 0.9800 C(17)-H(17B) 0.9800 C(17)-H(17C) 0.9800 C(13)-O(2)-C(14) 116.24(11) C(4)-O(4)-H(4A) 109.5 C(5)-C(1)-C(11) 112.46(11) C(5)-C(1)-C(12) 107.26(11) C(11)-C(1)-C(12) 110.16(11) C(5)-C(1)-C(2) 102.89(10) C(11)-C(1)-C(2) 111.82(10) C(12)-C(1)-C(2) 111.99(11) C(3)-C(2)-C(16) 109.39(11) C(3)-C(2)-C(13) 107.97(10) C(16)-C(2)-C(13) 108.43(11) C(3)-C(2)-C(1) 103.62(10) C(16)-C(2)-C(1) 116.11(11) C(13)-C(2)-C(1) 110.98(10) O(3)-C(3)-C(4) 126.74(12) O(3)-C(3)-C(2) 124.30(12) C(4)-C(3)-C(2) 108.93(11) C(5)-C(4)-O(4) 125.65(12) C(5)-C(4)-C(3) 111.33(11) O(4)-C(4)-C(3) 122.99(12) C(4)-C(5)-C(17) 124.11(12) C(4)-C(5)-C(1) 112.57(11) C(17)-C(5)-C(1) 123.02(12) C(7)-C(6)-C(11) 121.30(15) C(7)-C(6)-H(6A) 119.3 C(11)-C(6)-H(6A) 119.3 C(8)-C(7)-C(6) 120.10(16) C(8)-C(7)-H(7A) 119.9 C(6)-C(7)-H(7A) 119.9 C(7)-C(8)-C(9) 119.36(15) C(7)-C(8)-H(8A) 120.3 C(9)-C(8)-H(8A) 120.3 C(8)-C(9)-C(10) 120.65(16) C(8)-C(9)-H(9A) 119.7 C(10)-C(9)-H(9A) 119.7 C(9)-C(10)-C(11) 120.70(15) C(9)-C(10)-H(10) 119.7 C(11)-C(10)-H(10) 119.7 C(6)-C(11)-C(10) 117.89(13) C(6)-C(11)-C(1) 121.57(12) C(10)-C(11)-C(1) 120.50(12) C(1)-C(12)-H(12A) 109.5 C(1)-C(12)-H(12B) 109.5 H(12A)-C(12)-H(12B) 109.5 C(1)-C(12)-H(12C) 109.5 H(12A)-C(12)-H(12C) 109.5 H(12B)-C(12)-H(12C) 109.5 O(1)-C(13)-O(2) 124.19(13) O(1)-C(13)-C(2) 124.46(13) O(2)-C(13)-C(2) 111.35(11) O(2)-C(14)-C(15) 107.61(14) O(2)-C(14)-H(14A) 110.2 C(15)-C(14)-H(14A) 110.2 O(2)-C(14)-H(14B) 110.2 C(15)-C(14)-H(14B) 110.2 H(14A)-C(14)-H(14B) 108.5 C(14)-C(15)-H(15A) 109.5 C(14)-C(15)-H(15B) 109.5 H(15A)-C(15)-H(15B) 109.5 C(14)-C(15)-H(15C) 109.5 H(15A)-C(15)-H(15C) 109.5 H(15B)-C(15)-H(15C) 109.5 C(2)-C(16)-H(16A) 109.5 C(2)-C(16)-H(16B) 109.5 H(16A)-C(16)-H(16B) 109.5 C(2)-C(16)-H(16C) 109.5 H(16A)-C(16)-H(16C) 109.5 H(16B)-C(16)-H(16C) 109.5 C(5)-C(17)-H(17A) 109.5 C(5)-C(17)-H(17B) 109.5 H(17A)-C(17)-H(17B) 109.5 C(5)-C(17)-H(17C) 109.5 H(17A)-C(17)-H(17C) 109.5 H(17B)-C(17)-H(17C) 109.5 _____________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 4. Anisotropic displacement parameters (A^2 x 10^3) for marc. 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 _______________________________________________________________________ O(1) 22(1) 39(1) 51(1) -5(1) 9(1) 6(1) O(2) 26(1) 28(1) 25(1) -3(1) 8(1) 0(1) O(3) 26(1) 29(1) 45(1) 13(1) 14(1) -1(1) O(4) 18(1) 34(1) 38(1) 10(1) 7(1) -1(1) C(1) 22(1) 20(1) 20(1) 1(1) 6(1) -1(1) C(2) 17(1) 22(1) 20(1) 3(1) 5(1) -1(1) C(3) 21(1) 24(1) 20(1) 0(1) 7(1) -2(1) C(4) 18(1) 27(1) 20(1) 0(1) 6(1) 1(1) C(5) 22(1) 25(1) 20(1) 0(1) 7(1) 2(1) C(6) 35(1) 28(1) 26(1) 3(1) 10(1) 0(1) C(7) 54(1) 41(1) 25(1) 7(1) 15(1) 9(1) C(8) 50(1) 53(1) 39(1) 21(1) 29(1) 17(1) C(9) 30(1) 57(1) 47(1) 22(1) 20(1) 9(1) C(10) 25(1) 38(1) 34(1) 12(1) 10(1) 4(1) C(11) 26(1) 20(1) 25(1) 5(1) 11(1) 3(1) C(12) 34(1) 28(1) 30(1) -7(1) 9(1) -6(1) C(13) 21(1) 19(1) 28(1) 5(1) 7(1) -2(1) C(14) 47(1) 31(1) 32(1) -6(1) 18(1) 4(1) C(15) 64(1) 44(1) 30(1) -8(1) 9(1) -3(1) C(16) 27(1) 38(1) 25(1) 6(1) -2(1) -3(1) C(17) 33(1) 29(1) 38(1) 8(1) 10(1) 7(1) _______________________________________________________________________ Table 5. Hydrogen coordinates ( x 10^4) and isotropic displacement parameters (A^2 x 10^3) for marc. ________________________________________________________________ x y z U(eq) ________________________________________________________________ H(4A) -283 6768 9530 44 H(6A) 814 8987 7776 35 H(7A) 1245 9346 6721 47 H(8A) 2177 10272 6908 53 H(9A) 2675 10804 8158 51 H(10) 2247 10453 9217 38 H(12A) 1345 12049 9708 46 H(12B) 1810 10655 10146 46 H(12C) 1202 10685 10355 46 H(14A) 1476 3383 8008 42 H(14B) 1631 5339 7676 42 H(15A) 542 3757 7367 69 H(15B) 945 3844 6756 69 H(15C) 695 5708 7037 69 H(16A) 1553 7843 10819 46 H(16B) 2078 7589 10413 46 H(16C) 1734 5821 10598 46 H(17A) -129 10837 8600 49 H(17B) 417 11533 8313 49 H(17C) 315 12121 9148 49 ________________________________________________________________ Table 6. Torsion angles [deg] for marc. ________________________________________________________________ C(5)-C(1)-C(2)-C(3) -7.79(12) C(11)-C(1)-C(2)-C(3) -128.72(11) C(12)-C(1)-C(2)-C(3) 107.09(12) C(5)-C(1)-C(2)-C(16) -127.74(12) C(11)-C(1)-C(2)-C(16) 111.33(13) C(12)-C(1)-C(2)-C(16) -12.86(15) C(5)-C(1)-C(2)-C(13) 107.86(11) C(11)-C(1)-C(2)-C(13) -13.06(14) C(12)-C(1)-C(2)-C(13) -137.26(11) C(16)-C(2)-C(3)-O(3) -46.57(18) C(13)-C(2)-C(3)-O(3) 71.24(16) C(1)-C(2)-C(3)-O(3) -171.00(13) C(16)-C(2)-C(3)-C(4) 131.43(12) C(13)-C(2)-C(3)-C(4) -110.77(12) C(1)-C(2)-C(3)-C(4) 7.00(13) O(3)-C(3)-C(4)-C(5) 174.64(13) C(2)-C(3)-C(4)-C(5) -3.29(15) O(3)-C(3)-C(4)-O(4) -3.5(2) C(2)-C(3)-C(4)-O(4) 178.59(11) O(4)-C(4)-C(5)-C(17) 1.9(2) C(3)-C(4)-C(5)-C(17) -176.16(13) O(4)-C(4)-C(5)-C(1) 175.74(12) C(3)-C(4)-C(5)-C(1) -2.32(16) C(11)-C(1)-C(5)-C(4) 127.01(12) C(12)-C(1)-C(5)-C(4) -111.72(13) C(2)-C(1)-C(5)-C(4) 6.53(14) C(11)-C(1)-C(5)-C(17) -59.06(16) C(12)-C(1)-C(5)-C(17) 62.20(16) C(2)-C(1)-C(5)-C(17) -179.55(12) C(11)-C(6)-C(7)-C(8) -0.3(2) C(6)-C(7)-C(8)-C(9) 0.3(3) C(7)-C(8)-C(9)-C(10) -0.3(3) C(8)-C(9)-C(10)-C(11) 0.4(3) C(7)-C(6)-C(11)-C(10) 0.4(2) C(7)-C(6)-C(11)-C(1) -176.99(13) C(9)-C(10)-C(11)-C(6) -0.5(2) C(9)-C(10)-C(11)-C(1) 176.97(14) C(5)-C(1)-C(11)-C(6) -23.64(17) C(12)-C(1)-C(11)-C(6) -143.24(13) C(2)-C(1)-C(11)-C(6) 91.55(14) C(5)-C(1)-C(11)-C(10) 159.01(12) C(12)-C(1)-C(11)-C(10) 39.42(17) C(2)-C(1)-C(11)-C(10) -85.79(15) C(14)-O(2)-C(13)-O(1) -8.78(19) C(14)-O(2)-C(13)-C(2) 170.95(11) C(3)-C(2)-C(13)-O(1) -142.83(13) C(16)-C(2)-C(13)-O(1) -24.41(17) C(1)-C(2)-C(13)-O(1) 104.24(15) C(3)-C(2)-C(13)-O(2) 37.44(14) C(16)-C(2)-C(13)-O(2) 155.86(11) C(1)-C(2)-C(13)-O(2) -75.49(13) C(13)-O(2)-C(14)-C(15) -171.29(12) ________________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 7. Hydrogen bonds for marc [A and deg.]. ____________________________________________________________________________ D-H...A d(D-H) d(H...A) d(D...A) <(DHA) O(4)-H(4A)...O(3)#1 0.84 1.92 2.7340(15) 162.4 ____________________________________________________________________________ Symmetry transformations used to generate equivalent atoms: #1 -x,-y+1,-z+2