Table 1. Crystal data and structure refinement for pr4. Identification code shelxl Empirical formula C32 H22 N2 O Formula weight 450.52 Temperature 293(2) K Wavelength 0.71073 A Crystal system, space group Monoclinic, P21/c Unit cell dimensions a = 12.3316(7) A alpha = 90 deg. b = 21.3475(11) A beta = 92.340(3) deg. c = 8.8212(5) A gamma = 90 deg. Volume 2320.2(2) A^3 Z, Calculated density 4, 1.290 Mg/m^3 Absorption coefficient 0.078 mm^-1 F(000) 944 Crystal size 0.35 x 0.30 x 0.25 mm Theta range for data collection 2.50 to 30.64 deg. Limiting indices -17<=h<=17, -28<=k<=30, -12<=l<=12 Reflections collected / unique 29016 / 7155 [R(int) = 0.0401] Completeness to theta = 30.64 99.8 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.9807 and 0.9232 Refinement method Full-matrix least-squares on F^2 Data / restraints / parameters 7155 / 0 / 317 Goodness-of-fit on F^2 1.024 Final R indices [I>2sigma(I)] R1 = 0.0528, wR2 = 0.1186 R indices (all data) R1 = 0.1092, wR2 = 0.1422 Largest diff. peak and hole 0.170 and -0.212 e.A^-3 Table 2. Atomic coordinates ( x 10^4) and equivalent isotropic displacement parameters (A^2 x 10^3) for pr4. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. ________________________________________________________________ x y z U(eq) ________________________________________________________________ C(1) 1654(1) 4554(1) 2458(2) 39(1) C(2) 1640(1) 4081(1) 1312(2) 40(1) C(3) 982(1) 4123(1) -15(2) 50(1) C(4) 1046(1) 3682(1) -1125(2) 58(1) C(5) 1750(1) 3179(1) -931(2) 60(1) C(6) 2372(1) 3119(1) 376(2) 53(1) C(7) 2346(1) 3565(1) 1541(2) 42(1) C(8) 3034(1) 3519(1) 2930(2) 41(1) C(9) 3779(1) 3025(1) 3160(2) 51(1) C(10) 4436(1) 2982(1) 4445(2) 56(1) C(11) 4355(1) 3419(1) 5585(2) 55(1) C(12) 3642(1) 3906(1) 5420(2) 49(1) C(13) 2995(1) 3979(1) 4086(2) 40(1) C(14) 2295(1) 4503(1) 3763(2) 38(1) C(15) 1398(1) 5400(1) 3680(2) 40(1) C(16) 1084(1) 6041(1) 4120(2) 42(1) C(17) 248(1) 6137(1) 5057(2) 57(1) C(18) -77(2) 6742(1) 5428(2) 73(1) C(19) 452(2) 7245(1) 4889(2) 71(1) C(20) 1333(1) 7174(1) 3941(2) 53(1) C(21) 1912(2) 7690(1) 3382(2) 71(1) C(22) 2749(2) 7607(1) 2459(2) 75(1) C(23) 3050(2) 7005(1) 2037(2) 68(1) C(24) 2521(1) 6492(1) 2551(2) 52(1) C(25) 1652(1) 6560(1) 3529(2) 42(1) C(26) 2632(1) 5255(1) 5967(2) 39(1) C(27) 3666(1) 5487(1) 5972(2) 47(1) C(28) 4200(1) 5653(1) 7318(2) 49(1) C(29) 3676(1) 5589(1) 8658(2) 46(1) C(30) 2620(1) 5373(1) 8645(2) 56(1) C(31) 2096(1) 5203(1) 7305(2) 50(1) C(32) 5238(1) 5931(1) 10120(2) 74(1) N(1) 1092(1) 5114(1) 2416(1) 44(1) N(2) 2117(1) 5053(1) 4559(1) 40(1) O(1) 4144(1) 5719(1) 10058(1) 67(1) ________________________________________________________________ Table 3. Bond lengths [A] and angles [deg] for pr4. _____________________________________________________________ C(1)-C(14) 1.3744(18) C(1)-N(1) 1.3809(16) C(1)-C(2) 1.4279(18) C(2)-C(3) 1.3998(19) C(2)-C(7) 1.4142(19) C(3)-C(4) 1.363(2) C(3)-H(3) 0.9300 C(4)-C(5) 1.386(2) C(4)-H(4) 0.9300 C(5)-C(6) 1.364(2) C(5)-H(5) 0.9300 C(6)-C(7) 1.4025(19) C(6)-H(6) 0.9300 C(7)-C(8) 1.4649(19) C(8)-C(9) 1.4073(19) C(8)-C(13) 1.4180(19) C(9)-C(10) 1.370(2) C(9)-H(9) 0.9300 C(10)-C(11) 1.378(2) C(10)-H(10) 0.9300 C(11)-C(12) 1.366(2) C(11)-H(11) 0.9300 C(12)-C(13) 1.4028(19) C(12)-H(12) 0.9300 C(13)-C(14) 1.4349(18) C(14)-N(2) 1.3897(16) C(15)-N(1) 1.3132(17) C(15)-N(2) 1.3710(17) C(15)-C(16) 1.4779(18) C(16)-C(17) 1.363(2) C(16)-C(25) 1.4214(19) C(17)-C(18) 1.395(2) C(17)-H(17) 0.9300 C(18)-C(19) 1.353(3) C(18)-H(18) 0.9300 C(19)-C(20) 1.405(2) C(19)-H(19) 0.9300 C(20)-C(21) 1.413(2) C(20)-C(25) 1.4195(19) C(21)-C(22) 1.352(3) C(21)-H(21) 0.9300 C(22)-C(23) 1.393(2) C(22)-H(22) 0.9300 C(23)-C(24) 1.360(2) C(23)-H(23) 0.9300 C(24)-C(25) 1.411(2) C(24)-H(24) 0.9300 C(26)-C(27) 1.3681(19) C(26)-C(31) 1.380(2) C(26)-N(2) 1.4375(16) C(27)-C(28) 1.3799(19) C(27)-H(27) 0.9300 C(28)-C(29) 1.377(2) C(28)-H(28) 0.9300 C(29)-O(1) 1.3696(16) C(29)-C(30) 1.382(2) C(30)-C(31) 1.372(2) C(30)-H(30) 0.9300 C(31)-H(31) 0.9300 C(32)-O(1) 1.423(2) C(32)-H(32A) 0.9600 C(32)-H(32B) 0.9600 C(32)-H(32C) 0.9600 C(14)-C(1)-N(1) 111.22(11) C(14)-C(1)-C(2) 121.82(12) N(1)-C(1)-C(2) 126.92(12) C(3)-C(2)-C(7) 120.12(13) C(3)-C(2)-C(1) 122.49(12) C(7)-C(2)-C(1) 117.38(12) C(4)-C(3)-C(2) 120.54(14) C(4)-C(3)-H(3) 119.7 C(2)-C(3)-H(3) 119.7 C(3)-C(4)-C(5) 120.03(15) C(3)-C(4)-H(4) 120.0 C(5)-C(4)-H(4) 120.0 C(6)-C(5)-C(4) 120.31(15) C(6)-C(5)-H(5) 119.8 C(4)-C(5)-H(5) 119.8 C(5)-C(6)-C(7) 121.81(14) C(5)-C(6)-H(6) 119.1 C(7)-C(6)-H(6) 119.1 C(6)-C(7)-C(2) 117.13(13) C(6)-C(7)-C(8) 122.54(13) C(2)-C(7)-C(8) 120.30(12) C(9)-C(8)-C(13) 117.15(13) C(9)-C(8)-C(7) 121.55(13) C(13)-C(8)-C(7) 121.28(12) C(10)-C(9)-C(8) 122.04(15) C(10)-C(9)-H(9) 119.0 C(8)-C(9)-H(9) 119.0 C(9)-C(10)-C(11) 119.98(14) C(9)-C(10)-H(10) 120.0 C(11)-C(10)-H(10) 120.0 C(12)-C(11)-C(10) 120.25(15) C(12)-C(11)-H(11) 119.9 C(10)-C(11)-H(11) 119.9 C(11)-C(12)-C(13) 121.00(14) C(11)-C(12)-H(12) 119.5 C(13)-C(12)-H(12) 119.5 C(12)-C(13)-C(8) 119.45(12) C(12)-C(13)-C(14) 124.72(12) C(8)-C(13)-C(14) 115.81(12) C(1)-C(14)-N(2) 105.01(11) C(1)-C(14)-C(13) 123.28(12) N(2)-C(14)-C(13) 131.68(12) N(1)-C(15)-N(2) 112.69(12) N(1)-C(15)-C(16) 125.77(12) N(2)-C(15)-C(16) 121.43(12) C(17)-C(16)-C(25) 120.09(13) C(17)-C(16)-C(15) 120.72(13) C(25)-C(16)-C(15) 119.17(12) C(16)-C(17)-C(18) 120.86(15) C(16)-C(17)-H(17) 119.6 C(18)-C(17)-H(17) 119.6 C(19)-C(18)-C(17) 120.34(16) C(19)-C(18)-H(18) 119.8 C(17)-C(18)-H(18) 119.8 C(18)-C(19)-C(20) 121.23(15) C(18)-C(19)-H(19) 119.4 C(20)-C(19)-H(19) 119.4 C(19)-C(20)-C(21) 122.48(15) C(19)-C(20)-C(25) 118.78(14) C(21)-C(20)-C(25) 118.75(15) C(22)-C(21)-C(20) 121.17(16) C(22)-C(21)-H(21) 119.4 C(20)-C(21)-H(21) 119.4 C(21)-C(22)-C(23) 119.98(17) C(21)-C(22)-H(22) 120.0 C(23)-C(22)-H(22) 120.0 C(24)-C(23)-C(22) 121.09(17) C(24)-C(23)-H(23) 119.5 C(22)-C(23)-H(23) 119.5 C(23)-C(24)-C(25) 120.57(15) C(23)-C(24)-H(24) 119.7 C(25)-C(24)-H(24) 119.7 C(24)-C(25)-C(20) 118.44(13) C(24)-C(25)-C(16) 122.89(13) C(20)-C(25)-C(16) 118.67(13) C(27)-C(26)-C(31) 120.31(13) C(27)-C(26)-N(2) 119.36(12) C(31)-C(26)-N(2) 120.32(12) C(26)-C(27)-C(28) 120.55(13) C(26)-C(27)-H(27) 119.7 C(28)-C(27)-H(27) 119.7 C(29)-C(28)-C(27) 119.24(13) C(29)-C(28)-H(28) 120.4 C(27)-C(28)-H(28) 120.4 O(1)-C(29)-C(28) 123.97(13) O(1)-C(29)-C(30) 115.94(13) C(28)-C(29)-C(30) 120.08(13) C(31)-C(30)-C(29) 120.38(13) C(31)-C(30)-H(30) 119.8 C(29)-C(30)-H(30) 119.8 C(30)-C(31)-C(26) 119.39(13) C(30)-C(31)-H(31) 120.3 C(26)-C(31)-H(31) 120.3 O(1)-C(32)-H(32A) 109.5 O(1)-C(32)-H(32B) 109.5 H(32A)-C(32)-H(32B) 109.5 O(1)-C(32)-H(32C) 109.5 H(32A)-C(32)-H(32C) 109.5 H(32B)-C(32)-H(32C) 109.5 C(15)-N(1)-C(1) 104.66(11) C(15)-N(2)-C(14) 106.41(11) C(15)-N(2)-C(26) 125.40(11) C(14)-N(2)-C(26) 128.04(11) C(29)-O(1)-C(32) 117.59(12) _____________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 4. Anisotropic displacement parameters (A^2 x 10^3) for pr4. 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) 38(1) 39(1) 40(1) 2(1) 2(1) -2(1) C(2) 41(1) 40(1) 40(1) 0(1) 4(1) -6(1) C(3) 54(1) 47(1) 48(1) 1(1) -7(1) -3(1) C(4) 66(1) 59(1) 48(1) -5(1) -10(1) -12(1) C(5) 68(1) 56(1) 55(1) -15(1) 1(1) -10(1) C(6) 55(1) 48(1) 57(1) -10(1) 5(1) -1(1) C(7) 40(1) 43(1) 43(1) -2(1) 7(1) -6(1) C(8) 38(1) 40(1) 46(1) 2(1) 7(1) -2(1) C(9) 54(1) 44(1) 56(1) 1(1) 10(1) 4(1) C(10) 51(1) 50(1) 66(1) 10(1) 4(1) 12(1) C(11) 55(1) 54(1) 56(1) 11(1) -7(1) 4(1) C(12) 51(1) 48(1) 47(1) 3(1) -3(1) 2(1) C(13) 36(1) 41(1) 42(1) 3(1) 2(1) -2(1) C(14) 37(1) 39(1) 37(1) 0(1) 3(1) -3(1) C(15) 38(1) 41(1) 41(1) 1(1) 2(1) 0(1) C(16) 41(1) 45(1) 40(1) -2(1) -3(1) 3(1) C(17) 54(1) 58(1) 61(1) -3(1) 14(1) -1(1) C(18) 67(1) 72(1) 81(1) -14(1) 27(1) 9(1) C(19) 75(1) 54(1) 85(1) -18(1) 13(1) 13(1) C(20) 55(1) 46(1) 58(1) -6(1) -3(1) 2(1) C(21) 85(1) 44(1) 83(1) -2(1) -4(1) -3(1) C(22) 82(1) 58(1) 86(1) 13(1) 7(1) -17(1) C(23) 62(1) 71(1) 73(1) 10(1) 14(1) -8(1) C(24) 51(1) 51(1) 55(1) 2(1) 6(1) 2(1) C(25) 42(1) 44(1) 41(1) -1(1) -4(1) 3(1) C(26) 41(1) 40(1) 37(1) -1(1) 0(1) -2(1) C(27) 45(1) 58(1) 38(1) 0(1) 6(1) -9(1) C(28) 42(1) 59(1) 45(1) -3(1) 2(1) -13(1) C(29) 51(1) 51(1) 37(1) -4(1) -2(1) -4(1) C(30) 54(1) 77(1) 37(1) -2(1) 11(1) -12(1) C(31) 41(1) 63(1) 45(1) -1(1) 6(1) -11(1) C(32) 64(1) 95(1) 61(1) -14(1) -16(1) -16(1) N(1) 45(1) 42(1) 44(1) -1(1) -4(1) 1(1) N(2) 39(1) 42(1) 38(1) -2(1) 0(1) -1(1) O(1) 64(1) 94(1) 41(1) -11(1) -2(1) -17(1) _______________________________________________________________________ Table 5. Hydrogen coordinates ( x 10^4) and isotropic displacement parameters (A^2 x 10^3) for pr4. ________________________________________________________________ x y z U(eq) ________________________________________________________________ H(3) 497 4454 -141 60 H(4) 617 3718 -2013 69 H(5) 1799 2882 -1695 72 H(6) 2825 2773 497 63 H(9) 3827 2719 2415 61 H(10) 4937 2657 4549 67 H(11) 4787 3382 6469 66 H(12) 3584 4194 6204 59 H(17) -111 5795 5455 69 H(18) -660 6800 6049 87 H(19) 229 7645 5150 85 H(21) 1714 8094 3654 85 H(22) 3124 7952 2106 90 H(23) 3621 6952 1393 82 H(24) 2735 6095 2256 63 H(27) 4011 5534 5061 56 H(28) 4906 5806 7319 58 H(30) 2261 5342 9549 67 H(31) 1387 5055 7298 60 H(32A) 5687 5630 9635 111 H(32B) 5484 5979 11160 111 H(32C) 5283 6326 9607 111 ________________________________________________________________ Table 6. Torsion angles [deg] for pr4. ________________________________________________________________ C(14)-C(1)-C(2)-C(3) 179.25(13) N(1)-C(1)-C(2)-C(3) -3.2(2) C(14)-C(1)-C(2)-C(7) -2.35(19) N(1)-C(1)-C(2)-C(7) 175.17(12) C(7)-C(2)-C(3)-C(4) -2.7(2) C(1)-C(2)-C(3)-C(4) 175.66(13) C(2)-C(3)-C(4)-C(5) 1.4(2) C(3)-C(4)-C(5)-C(6) 0.8(2) C(4)-C(5)-C(6)-C(7) -1.7(2) C(5)-C(6)-C(7)-C(2) 0.4(2) C(5)-C(6)-C(7)-C(8) -177.93(14) C(3)-C(2)-C(7)-C(6) 1.77(19) C(1)-C(2)-C(7)-C(6) -176.67(12) C(3)-C(2)-C(7)-C(8) -179.86(12) C(1)-C(2)-C(7)-C(8) 1.71(18) C(6)-C(7)-C(8)-C(9) 1.1(2) C(2)-C(7)-C(8)-C(9) -177.15(13) C(6)-C(7)-C(8)-C(13) 179.65(13) C(2)-C(7)-C(8)-C(13) 1.36(19) C(13)-C(8)-C(9)-C(10) 0.6(2) C(7)-C(8)-C(9)-C(10) 179.18(13) C(8)-C(9)-C(10)-C(11) 2.1(2) C(9)-C(10)-C(11)-C(12) -1.8(2) C(10)-C(11)-C(12)-C(13) -1.2(2) C(11)-C(12)-C(13)-C(8) 3.9(2) C(11)-C(12)-C(13)-C(14) -174.40(13) C(9)-C(8)-C(13)-C(12) -3.53(19) C(7)-C(8)-C(13)-C(12) 177.90(12) C(9)-C(8)-C(13)-C(14) 174.92(12) C(7)-C(8)-C(13)-C(14) -3.66(18) N(1)-C(1)-C(14)-N(2) 0.24(14) C(2)-C(1)-C(14)-N(2) 178.12(11) N(1)-C(1)-C(14)-C(13) -177.98(11) C(2)-C(1)-C(14)-C(13) -0.1(2) C(12)-C(13)-C(14)-C(1) -178.54(13) C(8)-C(13)-C(14)-C(1) 3.11(19) C(12)-C(13)-C(14)-N(2) 3.8(2) C(8)-C(13)-C(14)-N(2) -174.60(13) N(1)-C(15)-C(16)-C(17) 97.27(18) N(2)-C(15)-C(16)-C(17) -86.86(17) N(1)-C(15)-C(16)-C(25) -81.47(18) N(2)-C(15)-C(16)-C(25) 94.40(16) C(25)-C(16)-C(17)-C(18) 1.2(2) C(15)-C(16)-C(17)-C(18) -177.51(15) C(16)-C(17)-C(18)-C(19) -1.6(3) C(17)-C(18)-C(19)-C(20) 0.4(3) C(18)-C(19)-C(20)-C(21) -178.89(18) C(18)-C(19)-C(20)-C(25) 1.1(3) C(19)-C(20)-C(21)-C(22) -179.33(18) C(25)-C(20)-C(21)-C(22) 0.7(3) C(20)-C(21)-C(22)-C(23) 0.3(3) C(21)-C(22)-C(23)-C(24) -0.7(3) C(22)-C(23)-C(24)-C(25) 0.0(3) C(23)-C(24)-C(25)-C(20) 1.0(2) C(23)-C(24)-C(25)-C(16) -178.90(14) C(19)-C(20)-C(25)-C(24) 178.66(15) C(21)-C(20)-C(25)-C(24) -1.3(2) C(19)-C(20)-C(25)-C(16) -1.4(2) C(21)-C(20)-C(25)-C(16) 178.58(14) C(17)-C(16)-C(25)-C(24) -179.80(14) C(15)-C(16)-C(25)-C(24) -1.1(2) C(17)-C(16)-C(25)-C(20) 0.3(2) C(15)-C(16)-C(25)-C(20) 179.02(12) C(31)-C(26)-C(27)-C(28) 2.2(2) N(2)-C(26)-C(27)-C(28) -176.51(12) C(26)-C(27)-C(28)-C(29) -0.8(2) C(27)-C(28)-C(29)-O(1) 177.63(14) C(27)-C(28)-C(29)-C(30) -1.2(2) O(1)-C(29)-C(30)-C(31) -177.10(14) C(28)-C(29)-C(30)-C(31) 1.9(2) C(29)-C(30)-C(31)-C(26) -0.5(2) C(27)-C(26)-C(31)-C(30) -1.6(2) N(2)-C(26)-C(31)-C(30) 177.13(13) N(2)-C(15)-N(1)-C(1) -0.98(15) C(16)-C(15)-N(1)-C(1) 175.20(13) C(14)-C(1)-N(1)-C(15) 0.43(15) C(2)-C(1)-N(1)-C(15) -177.31(13) N(1)-C(15)-N(2)-C(14) 1.15(15) C(16)-C(15)-N(2)-C(14) -175.22(11) N(1)-C(15)-N(2)-C(26) 176.90(11) C(16)-C(15)-N(2)-C(26) 0.5(2) C(1)-C(14)-N(2)-C(15) -0.80(14) C(13)-C(14)-N(2)-C(15) 177.21(13) C(1)-C(14)-N(2)-C(26) -176.39(12) C(13)-C(14)-N(2)-C(26) 1.6(2) C(27)-C(26)-N(2)-C(15) -98.37(16) C(31)-C(26)-N(2)-C(15) 82.92(17) C(27)-C(26)-N(2)-C(14) 76.45(17) C(31)-C(26)-N(2)-C(14) -102.27(17) C(28)-C(29)-O(1)-C(32) -0.2(2) C(30)-C(29)-O(1)-C(32) 178.73(15) ________________________________________________________________ Symmetry transformations used to generate equivalent atoms: