Table 1. Crystal data and structure refinement for a20611b. Identification code a20611b Empirical formula C23 H16 F N O2 Formula weight 357.37 Temperature 293(2) K Wavelength 0.71073 A Crystal system, space group Monoclinic, P2(1)/c Unit cell dimensions a = 17.532(4) A alpha = 90 deg. b = 7.5384(19) A beta = 100.059(4) deg. c = 13.756(3) A gamma = 90 deg. Volume 1790.1(8) A^3 Z, Calculated density 4, 1.326 Mg/m^3 Absorption coefficient 0.092 mm^-1 F(000) 744 Crystal size 0.12 x 0.10 x 0.08 mm Theta range for data collection 2.36 to 25.01 deg. Limiting indices -19<=h<=20, -6<=k<=8, -16<=l<=15 Reflections collected / unique 7089 / 3148 [R(int) = 0.1360] Completeness to theta = 25.01 99.9 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.9927 and 0.9891 Refinement method Full-matrix least-squares on F^2 Data / restraints / parameters 3148 / 0 / 244 Goodness-of-fit on F^2 0.922 Final R indices [I>2sigma(I)] R1 = 0.0694, wR2 = 0.1042 R indices (all data) R1 = 0.2367, wR2 = 0.1420 Largest diff. peak and hole 0.207 and -0.175 e.A^-3 Table 2. Atomic coordinates ( x 10^4) and equivalent isotropic displacement parameters (A^2 x 10^3) for a20611b. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. ________________________________________________________________ x y z U(eq) ________________________________________________________________ F(1) 296(2) 8954(4) 4040(2) 116(1) N(1) 4046(2) 1447(4) 604(2) 55(1) O(1) 3022(2) 5722(4) 2338(2) 66(1) O(2) 3061(2) 5697(3) 716(2) 49(1) C(1) 4766(3) 1963(6) 860(3) 59(1) C(2) 5001(3) 3706(6) 1141(3) 50(1) C(3) 5782(3) 4190(7) 1416(3) 59(1) C(4) 5976(3) 5894(8) 1670(3) 66(1) C(5) 5398(3) 7182(6) 1647(3) 60(1) C(6) 4637(3) 6770(6) 1373(3) 51(1) C(7) 4422(3) 5008(6) 1127(3) 45(1) C(8) 3656(3) 4405(6) 853(3) 45(1) C(9) 3474(3) 2685(6) 605(3) 48(1) C(10) 2787(2) 6254(6) 1532(4) 52(1) C(11) 2176(3) 7652(6) 1226(3) 75(2) C(12) 1668(3) 7998(6) 1974(3) 52(1) C(13) 926(3) 7384(6) 1842(3) 71(1) C(14) 458(3) 7716(7) 2534(5) 78(2) C(15) 750(3) 8668(7) 3341(4) 69(2) C(16) 1467(3) 9324(6) 3497(3) 67(1) C(17) 1927(2) 8999(6) 2806(4) 65(1) C(18) 2670(3) 2074(5) 255(3) 50(1) C(19) 2499(3) 1145(6) -618(3) 64(1) C(20) 1757(4) 583(6) -980(4) 78(2) C(21) 1174(3) 927(7) -461(5) 81(2) C(22) 1332(3) 1822(7) 423(4) 76(2) C(23) 2079(3) 2391(5) 776(3) 60(1) ________________________________________________________________ Table 3. Bond lengths [A] and angles [deg] for a20611b. _____________________________________________________________ F(1)-C(15) 1.369(5) N(1)-C(1) 1.309(4) N(1)-C(9) 1.370(5) O(1)-C(10) 1.183(4) O(2)-C(10) 1.363(4) O(2)-C(8) 1.414(4) C(1)-C(2) 1.410(5) C(2)-C(3) 1.404(5) C(2)-C(7) 1.410(5) C(3)-C(4) 1.359(6) C(4)-C(5) 1.399(5) C(5)-C(6) 1.358(5) C(6)-C(7) 1.406(5) C(7)-C(8) 1.406(5) C(8)-C(9) 1.364(5) C(9)-C(18) 1.480(5) C(10)-C(11) 1.510(5) C(11)-C(12) 1.497(5) C(12)-C(13) 1.362(5) C(12)-C(17) 1.379(5) C(13)-C(14) 1.384(6) C(14)-C(15) 1.346(6) C(15)-C(16) 1.333(6) C(16)-C(17) 1.371(5) C(18)-C(19) 1.377(5) C(18)-C(23) 1.381(5) C(19)-C(20) 1.376(5) C(20)-C(21) 1.371(6) C(21)-C(22) 1.375(6) C(22)-C(23) 1.383(5) C(1)-N(1)-C(9) 118.0(4) C(10)-O(2)-C(8) 117.4(3) N(1)-C(1)-C(2) 124.9(4) C(3)-C(2)-C(7) 119.2(4) C(3)-C(2)-C(1) 122.7(5) C(7)-C(2)-C(1) 118.1(4) C(4)-C(3)-C(2) 120.3(4) C(3)-C(4)-C(5) 120.1(4) C(6)-C(5)-C(4) 121.4(4) C(5)-C(6)-C(7) 119.4(4) C(6)-C(7)-C(8) 125.0(4) C(6)-C(7)-C(2) 119.5(4) C(8)-C(7)-C(2) 115.5(4) C(9)-C(8)-C(7) 123.0(4) C(9)-C(8)-O(2) 119.1(4) C(7)-C(8)-O(2) 117.4(4) C(8)-C(9)-N(1) 120.5(4) C(8)-C(9)-C(18) 123.0(4) N(1)-C(9)-C(18) 116.3(4) O(1)-C(10)-O(2) 123.5(4) O(1)-C(10)-C(11) 127.7(4) O(2)-C(10)-C(11) 108.7(4) C(12)-C(11)-C(10) 114.1(3) C(13)-C(12)-C(17) 117.7(4) C(13)-C(12)-C(11) 121.1(5) C(17)-C(12)-C(11) 121.1(5) C(12)-C(13)-C(14) 120.9(5) C(15)-C(14)-C(13) 118.6(5) C(16)-C(15)-C(14) 122.9(5) C(16)-C(15)-F(1) 118.5(5) C(14)-C(15)-F(1) 118.6(6) C(15)-C(16)-C(17) 118.3(4) C(16)-C(17)-C(12) 121.6(4) C(19)-C(18)-C(23) 118.2(4) C(19)-C(18)-C(9) 119.5(4) C(23)-C(18)-C(9) 122.3(4) C(20)-C(19)-C(18) 121.4(5) C(21)-C(20)-C(19) 119.8(5) C(20)-C(21)-C(22) 120.1(5) C(21)-C(22)-C(23) 119.6(5) C(18)-C(23)-C(22) 121.0(4) _____________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 4. Anisotropic displacement parameters (A^2 x 10^3) for a20611b. 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 _______________________________________________________________________ F(1) 106(2) 129(3) 130(2) 16(2) 73(2) 33(2) N(1) 67(3) 39(3) 62(2) 5(2) 20(2) 13(2) O(1) 81(2) 71(2) 48(2) 8(2) 17(2) 21(2) O(2) 59(2) 44(2) 46(2) 5(2) 17(1) 11(2) C(1) 61(4) 51(4) 66(3) 9(3) 16(3) 19(3) C(2) 55(3) 49(4) 46(3) 6(2) 15(2) 9(3) C(3) 54(3) 70(4) 53(3) 9(3) 9(2) 10(3) C(4) 60(4) 72(4) 65(3) 4(3) 7(2) -7(3) C(5) 71(4) 52(3) 56(3) 2(2) 12(3) -3(3) C(6) 60(4) 50(4) 44(3) -3(2) 10(2) 1(3) C(7) 53(3) 46(3) 37(2) 3(2) 14(2) 3(3) C(8) 54(3) 46(3) 39(3) 8(2) 20(2) 17(3) C(9) 62(4) 41(3) 42(3) 3(2) 15(2) 4(3) C(10) 59(3) 46(3) 54(3) 4(3) 21(3) 7(2) C(11) 97(4) 61(3) 70(3) 15(3) 27(3) 37(3) C(12) 50(3) 51(3) 59(3) 8(3) 18(3) 14(3) C(13) 71(4) 66(4) 71(4) -3(3) 0(3) 3(3) C(14) 42(3) 82(4) 108(4) 15(4) 4(3) -7(3) C(15) 59(4) 68(4) 86(4) 9(3) 34(3) 18(3) C(16) 60(4) 73(4) 71(3) -21(3) 15(3) 0(3) C(17) 46(3) 62(3) 86(4) -8(3) 14(3) -9(3) C(18) 67(4) 38(3) 50(3) 8(2) 19(3) 2(3) C(19) 75(4) 59(3) 61(3) -3(3) 19(3) -6(3) C(20) 88(4) 66(4) 77(4) -1(3) 8(4) -17(4) C(21) 72(4) 61(4) 105(4) 13(4) 2(4) -6(3) C(22) 70(4) 61(4) 102(4) 9(3) 31(3) 6(3) C(23) 70(4) 47(3) 67(3) 1(2) 20(3) -4(3) _______________________________________________________________________ Table 5. Hydrogen coordinates ( x 10^4) and isotropic displacement parameters (A^2 x 10^3) for a20611b. ________________________________________________________________ x y z U(eq) ________________________________________________________________ H(1) 5152 1117 858 70 H(3) 6168 3342 1424 71 H(4) 6494 6205 1861 79 H(5) 5539 8344 1822 72 H(6) 4261 7647 1350 62 H(11A) 2429 8751 1099 89 H(11B) 1853 7285 613 89 H(13) 731 6734 1279 85 H(14) -47 7291 2444 94 H(16) 1651 9985 4060 81 H(17) 2425 9464 2901 78 H(19) 2893 891 -969 77 H(20) 1652 -28 -1576 93 H(21) 672 554 -706 97 H(22) 938 2043 781 91 H(23) 2184 2995 1374 72 ________________________________________________________________ Table 6. Torsion angles [deg] for a20611b. ________________________________________________________________ C(9)-N(1)-C(1)-C(2) 0.0(6) N(1)-C(1)-C(2)-C(3) 179.6(4) N(1)-C(1)-C(2)-C(7) -1.4(6) C(7)-C(2)-C(3)-C(4) 0.3(6) C(1)-C(2)-C(3)-C(4) 179.3(4) C(2)-C(3)-C(4)-C(5) -0.9(6) C(3)-C(4)-C(5)-C(6) 0.1(6) C(4)-C(5)-C(6)-C(7) 1.2(6) C(5)-C(6)-C(7)-C(8) 178.6(4) C(5)-C(6)-C(7)-C(2) -1.7(5) C(3)-C(2)-C(7)-C(6) 0.9(5) C(1)-C(2)-C(7)-C(6) -178.1(4) C(3)-C(2)-C(7)-C(8) -179.4(3) C(1)-C(2)-C(7)-C(8) 1.6(5) C(6)-C(7)-C(8)-C(9) 179.1(4) C(2)-C(7)-C(8)-C(9) -0.6(5) C(6)-C(7)-C(8)-O(2) 6.9(5) C(2)-C(7)-C(8)-O(2) -172.8(3) C(10)-O(2)-C(8)-C(9) 102.9(4) C(10)-O(2)-C(8)-C(7) -84.6(4) C(7)-C(8)-C(9)-N(1) -0.7(6) O(2)-C(8)-C(9)-N(1) 171.3(3) C(7)-C(8)-C(9)-C(18) -175.9(4) O(2)-C(8)-C(9)-C(18) -3.9(5) C(1)-N(1)-C(9)-C(8) 1.0(5) C(1)-N(1)-C(9)-C(18) 176.5(3) C(8)-O(2)-C(10)-O(1) 0.4(6) C(8)-O(2)-C(10)-C(11) 178.7(4) O(1)-C(10)-C(11)-C(12) -18.7(7) O(2)-C(10)-C(11)-C(12) 163.1(4) C(10)-C(11)-C(12)-C(13) -105.1(5) C(10)-C(11)-C(12)-C(17) 77.0(5) C(17)-C(12)-C(13)-C(14) -1.7(7) C(11)-C(12)-C(13)-C(14) -179.7(4) C(12)-C(13)-C(14)-C(15) 0.3(7) C(13)-C(14)-C(15)-C(16) 0.9(7) C(13)-C(14)-C(15)-F(1) -178.2(4) C(14)-C(15)-C(16)-C(17) -0.5(7) F(1)-C(15)-C(16)-C(17) 178.5(4) C(15)-C(16)-C(17)-C(12) -1.0(7) C(13)-C(12)-C(17)-C(16) 2.1(7) C(11)-C(12)-C(17)-C(16) -179.9(4) C(8)-C(9)-C(18)-C(19) 126.9(4) N(1)-C(9)-C(18)-C(19) -48.4(5) C(8)-C(9)-C(18)-C(23) -53.5(6) N(1)-C(9)-C(18)-C(23) 131.1(4) C(23)-C(18)-C(19)-C(20) 1.8(6) C(9)-C(18)-C(19)-C(20) -178.7(4) C(18)-C(19)-C(20)-C(21) -1.0(7) C(19)-C(20)-C(21)-C(22) -0.4(7) C(20)-C(21)-C(22)-C(23) 0.8(7) C(19)-C(18)-C(23)-C(22) -1.3(6) C(9)-C(18)-C(23)-C(22) 179.2(4) C(21)-C(22)-C(23)-C(18) 0.0(7) ________________________________________________________________ Symmetry transformations used to generate equivalent atoms: