Table 1. Crystal data and structure refinement for ls. Identification code shelxl Empirical formula C23 H16 F N3 O3 Formula weight 401.39 Temperature 296(2) K Wavelength 0.71073 A Crystal system, space group Monoclinic, P21/n Unit cell dimensions a = 12.6990(4) A alpha = 90 deg. b = 9.0798(3) A beta = 101.3230(10) deg. c = 16.4608(5) A gamma = 90 deg. Volume 1861.06(10) A^3 Z, Calculated density 4, 1.433 Mg/m^3 Absorption coefficient 0.104 mm^-1 F(000) 832 Crystal size 0.35 x 0.25 x 0.20 mm Theta range for data collection 1.86 to 28.30 deg. Limiting indices -16<=h<=16, -12<=k<=10, -19<=l<=21 Reflections collected / unique 20635 / 4583 [R(int) = 0.0323] Completeness to theta = 28.30 99.1 % Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.9796 and 0.9646 Refinement method Full-matrix least-squares on F^2 Data / restraints / parameters 4583 / 0 / 272 Goodness-of-fit on F^2 1.060 Final R indices [I>2sigma(I)] R1 = 0.0443, wR2 = 0.1191 R indices (all data) R1 = 0.0736, wR2 = 0.1442 Largest diff. peak and hole 0.242 and -0.266 e.A^-3 Table 2. Atomic coordinates ( x 10^4) and equivalent isotropic displacement parameters (A^2 x 10^3) for ls. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. ________________________________________________________________ x y z U(eq) ________________________________________________________________ F(1) 1584(1) 3522(1) 6772(1) 66(1) O(1) 374(1) 10259(1) 8946(1) 45(1) O(2) -2254(1) 7602(2) 8538(1) 48(1) O(3) -1341(1) 5686(1) 9133(1) 46(1) N(1) 2886(1) 6696(1) 10351(1) 37(1) N(2) 3344(1) 9118(2) 10187(1) 39(1) N(3) 2071(1) 10863(2) 9502(1) 45(1) C(1) -3442(2) 9470(3) 7908(1) 69(1) C(2) -2330(1) 9057(2) 8319(1) 47(1) C(3) -1472(1) 9923(2) 8472(1) 45(1) C(4) -462(1) 9297(2) 8838(1) 37(1) C(5) -355(1) 7860(2) 9047(1) 33(1) C(6) 719(1) 7130(2) 9344(1) 30(1) C(7) 1550(1) 8325(2) 9588(1) 30(1) C(8) 2603(1) 8050(2) 10038(1) 31(1) C(9) 3924(1) 6215(2) 10744(1) 34(1) C(10) 3992(1) 5169(2) 11359(1) 47(1) C(11) 4968(2) 4566(2) 11711(1) 55(1) C(12) 5889(1) 5013(2) 11464(1) 52(1) C(13) 1383(1) 4386(2) 7399(1) 40(1) C(14) 1261(1) 5861(2) 7265(1) 44(1) C(15) 1060(1) 6736(2) 7902(1) 39(1) C(16) 979(1) 6136(2) 8661(1) 30(1) C(17) 5824(1) 6070(2) 10861(1) 47(1) C(18) 4850(1) 6671(2) 10491(1) 40(1) C(19) 3030(1) 10441(2) 9901(1) 45(1) C(20) 1363(1) 9764(2) 9360(1) 35(1) C(21) -1299(1) 6961(2) 8932(1) 37(1) C(22) 1108(1) 4632(2) 8768(1) 36(1) C(23) 1318(1) 3744(2) 8136(1) 41(1) ________________________________________________________________ Table 3. Selected bond lengths [A] and angles [deg] for ls. _____________________________________________________________ _____________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 4. Bond lengths [A] and angles [deg] for ls. _____________________________________________________________ F(1)-C(13) 1.3598(19) O(1)-C(4) 1.359(2) O(1)-C(20) 1.3812(19) O(2)-C(2) 1.368(2) O(2)-C(21) 1.3850(19) O(3)-C(21) 1.209(2) N(1)-C(8) 1.3543(19) N(1)-C(9) 1.4176(19) N(1)-H(1) 0.8600 N(2)-C(19) 1.322(2) N(2)-C(8) 1.3401(19) N(3)-C(19) 1.322(2) N(3)-C(20) 1.333(2) C(1)-C(2) 1.489(2) C(1)-H(1A) 0.9600 C(1)-H(1B) 0.9600 C(1)-H(1C) 0.9600 C(2)-C(3) 1.327(3) C(3)-C(4) 1.424(2) C(3)-H(3) 0.9300 C(4)-C(5) 1.349(2) C(5)-C(21) 1.431(2) C(5)-C(6) 1.509(2) C(6)-C(7) 1.512(2) C(6)-C(16) 1.527(2) C(6)-H(6) 0.9800 C(7)-C(20) 1.367(2) C(7)-C(8) 1.418(2) C(9)-C(10) 1.379(2) C(9)-C(18) 1.386(2) C(10)-C(11) 1.375(2) C(10)-H(10) 0.9300 C(11)-C(12) 1.372(3) C(11)-H(11) 0.9300 C(12)-C(17) 1.372(3) C(12)-H(12) 0.9300 C(13)-C(14) 1.361(2) C(13)-C(23) 1.364(2) C(14)-C(15) 1.380(2) C(14)-H(14) 0.9300 C(15)-C(16) 1.384(2) C(15)-H(15) 0.9300 C(16)-C(22) 1.383(2) C(17)-C(18) 1.380(2) C(17)-H(17) 0.9300 C(18)-H(18) 0.9300 C(19)-H(19) 0.9300 C(22)-C(23) 1.382(2) C(22)-H(22) 0.9300 C(23)-H(23) 0.9300 C(4)-O(1)-C(20) 117.80(12) C(2)-O(2)-C(21) 122.63(14) C(8)-N(1)-C(9) 127.36(13) C(8)-N(1)-H(1) 116.3 C(9)-N(1)-H(1) 116.3 C(19)-N(2)-C(8) 116.11(14) C(19)-N(3)-C(20) 113.18(15) C(2)-C(1)-H(1A) 109.5 C(2)-C(1)-H(1B) 109.5 H(1A)-C(1)-H(1B) 109.5 C(2)-C(1)-H(1C) 109.5 H(1A)-C(1)-H(1C) 109.5 H(1B)-C(1)-H(1C) 109.5 C(3)-C(2)-O(2) 120.60(15) C(3)-C(2)-C(1) 127.37(19) O(2)-C(2)-C(1) 112.03(17) C(2)-C(3)-C(4) 118.79(17) C(2)-C(3)-H(3) 120.6 C(4)-C(3)-H(3) 120.6 C(5)-C(4)-O(1) 123.48(14) C(5)-C(4)-C(3) 122.04(16) O(1)-C(4)-C(3) 114.47(15) C(4)-C(5)-C(21) 118.56(14) C(4)-C(5)-C(6) 123.08(14) C(21)-C(5)-C(6) 118.24(14) C(5)-C(6)-C(7) 108.11(12) C(5)-C(6)-C(16) 109.49(12) C(7)-C(6)-C(16) 112.31(12) C(5)-C(6)-H(6) 109.0 C(7)-C(6)-H(6) 109.0 C(16)-C(6)-H(6) 109.0 C(20)-C(7)-C(8) 113.98(14) C(20)-C(7)-C(6) 122.54(13) C(8)-C(7)-C(6) 123.42(13) N(2)-C(8)-N(1) 117.58(14) N(2)-C(8)-C(7) 121.67(14) N(1)-C(8)-C(7) 120.73(13) C(10)-C(9)-C(18) 119.49(15) C(10)-C(9)-N(1) 117.76(14) C(18)-C(9)-N(1) 122.57(15) C(11)-C(10)-C(9) 120.32(17) C(11)-C(10)-H(10) 119.8 C(9)-C(10)-H(10) 119.8 C(12)-C(11)-C(10) 120.54(18) C(12)-C(11)-H(11) 119.7 C(10)-C(11)-H(11) 119.7 C(17)-C(12)-C(11) 119.17(16) C(17)-C(12)-H(12) 120.4 C(11)-C(12)-H(12) 120.4 F(1)-C(13)-C(14) 118.45(15) F(1)-C(13)-C(23) 118.83(15) C(14)-C(13)-C(23) 122.72(16) C(13)-C(14)-C(15) 118.36(15) C(13)-C(14)-H(14) 120.8 C(15)-C(14)-H(14) 120.8 C(14)-C(15)-C(16) 121.14(15) C(14)-C(15)-H(15) 119.4 C(16)-C(15)-H(15) 119.4 C(22)-C(16)-C(15) 118.38(14) C(22)-C(16)-C(6) 121.85(13) C(15)-C(16)-C(6) 119.74(13) C(12)-C(17)-C(18) 121.20(17) C(12)-C(17)-H(17) 119.4 C(18)-C(17)-H(17) 119.4 C(17)-C(18)-C(9) 119.26(16) C(17)-C(18)-H(18) 120.4 C(9)-C(18)-H(18) 120.4 N(2)-C(19)-N(3) 128.62(16) N(2)-C(19)-H(19) 115.7 N(3)-C(19)-H(19) 115.7 N(3)-C(20)-C(7) 126.36(15) N(3)-C(20)-O(1) 111.04(14) C(7)-C(20)-O(1) 122.59(14) O(3)-C(21)-O(2) 116.71(15) O(3)-C(21)-C(5) 126.16(15) O(2)-C(21)-C(5) 117.11(15) C(23)-C(22)-C(16) 121.09(15) C(23)-C(22)-H(22) 119.5 C(16)-C(22)-H(22) 119.5 C(13)-C(23)-C(22) 118.30(15) C(13)-C(23)-H(23) 120.8 C(22)-C(23)-H(23) 120.8 _____________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 5. Anisotropic displacement parameters (A^2 x 10^3) for ls. 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) 91(1) 53(1) 58(1) -13(1) 24(1) 8(1) O(1) 39(1) 37(1) 57(1) 13(1) 2(1) 3(1) O(2) 29(1) 62(1) 49(1) 5(1) -3(1) 3(1) O(3) 33(1) 51(1) 53(1) 10(1) 2(1) -8(1) N(1) 24(1) 34(1) 51(1) 5(1) -2(1) -6(1) N(2) 33(1) 34(1) 48(1) 0(1) 6(1) -7(1) N(3) 45(1) 35(1) 54(1) 7(1) 7(1) -5(1) C(1) 42(1) 94(2) 63(1) 12(1) -9(1) 17(1) C(2) 34(1) 64(1) 39(1) 7(1) 1(1) 12(1) C(3) 43(1) 50(1) 42(1) 10(1) 5(1) 14(1) C(4) 32(1) 43(1) 35(1) 4(1) 6(1) 4(1) C(5) 27(1) 42(1) 30(1) 3(1) 5(1) 2(1) C(6) 27(1) 32(1) 31(1) 6(1) 4(1) -2(1) C(7) 28(1) 32(1) 30(1) 1(1) 6(1) -1(1) C(8) 30(1) 32(1) 33(1) 0(1) 8(1) -1(1) C(9) 28(1) 31(1) 40(1) -3(1) -1(1) -2(1) C(10) 34(1) 54(1) 52(1) 13(1) 4(1) -2(1) C(11) 46(1) 56(1) 58(1) 15(1) -4(1) 5(1) C(12) 32(1) 47(1) 70(1) -5(1) -8(1) 5(1) C(13) 37(1) 39(1) 42(1) -6(1) 6(1) 3(1) C(14) 52(1) 44(1) 37(1) 7(1) 13(1) 2(1) C(15) 46(1) 30(1) 42(1) 7(1) 11(1) 4(1) C(16) 23(1) 31(1) 34(1) 3(1) 1(1) -2(1) C(17) 29(1) 39(1) 72(1) -9(1) 7(1) -3(1) C(18) 32(1) 34(1) 53(1) -1(1) 7(1) -3(1) C(19) 41(1) 36(1) 59(1) 2(1) 9(1) -11(1) C(20) 33(1) 35(1) 36(1) 5(1) 7(1) 0(1) C(21) 28(1) 51(1) 31(1) 3(1) 4(1) 1(1) C(22) 35(1) 34(1) 36(1) 8(1) 1(1) -4(1) C(23) 42(1) 28(1) 50(1) 2(1) 2(1) 0(1) _______________________________________________________________________ Table 6. Hydrogen coordinates ( x 10^4) and isotropic displacement parameters (A^2 x 10^3) for ls. ________________________________________________________________ x y z U(eq) ________________________________________________________________ H(1) 2379 6055 10307 45 H(1A) -3490 10521 7849 103 H(1B) -3939 9138 8239 103 H(1C) -3612 9018 7371 103 H(3) -1529 10920 8342 54 H(6) 682 6528 9831 36 H(10) 3374 4870 11537 57 H(11) 5005 3850 12119 66 H(12) 6549 4604 11703 62 H(14) 1313 6269 6756 53 H(15) 976 7746 7821 46 H(17) 6448 6386 10699 57 H(18) 4815 7375 10076 48 H(19) 3553 11171 9994 54 H(22) 1053 4211 9273 43 H(23) 1411 2734 8212 49 ________________________________________________________________ Table 7. Selected torsion angles [deg] for ls. ________________________________________________________________