Table 1. Crystal data and structure refinement for ?. Identification code s92 Empirical formula C23 H26 N2 O3 Formula weight 378.46 Temperature 150(2) K Wavelength 0.71073 A Crystal system Monoclinic Space group P2(1)/n Unit cell dimensions a = 13.189(3) A alpha = 90 deg. b = 9.300(2) A beta = 102.79(3) deg. c = 16.258(3) A gamma = 90 deg. Volume 1944.7(7) A^3 Z 4 Density (calculated) 1.293 Mg/m^3 Absorption coefficient 0.086 mm^-1 F(000) 808 Crystal size 0.20 x 0.20 x 0.05 mm Theta range for data collection 2.57 to 25.25 deg. Index ranges -15<=h<=15, -11<=k<=11, -19<=l<=19 Reflections collected 11151 Independent reflections 3313 [R(int) = 0.1000] Max. and min. transmission 0.9957 and 0.9830 Refinement method Full-matrix least-squares on F^2 Data / restraints / parameters 3313 / 0 / 357 Goodness-of-fit on F^2 0.961 Final R indices [I>2sigma(I)] R1 = 0.0491, wR2 = 0.1124 R indices (all data) R1 = 0.0913, wR2 = 0.1324 Largest diff. peak and hole 0.260 and -0.294 e.A^-3 Table 2. Atomic coordinates ( x 10^4) and equivalent isotropic displacement parameters (A^2 x 10^3) for ?. U(eq) is defined as one third of the trace of the orthogonalized Uij tensor. ________________________________________________________________ x y z U(eq) ________________________________________________________________ O(1) 5518(1) -4199(2) -1401(1) 49(1) O(2) 2342(1) -6050(2) -907(1) 32(1) O(3) 1801(1) 2365(2) 1933(1) 50(1) N(1) 3321(1) -4511(2) -1905(1) 27(1) N(2) 2252(1) 166(2) 831(1) 28(1) C(1) 5053(2) -5569(3) -1614(2) 41(1) C(2) 4040(2) -5430(3) -2251(1) 33(1) C(3) 3805(2) -3090(2) -1699(2) 37(1) C(4) 4831(2) -3281(3) -1077(2) 45(1) C(5) 2288(2) -4420(2) -2463(1) 27(1) C(6) 2178(2) -4103(2) -3312(1) 32(1) C(7) 1204(2) -4079(3) -3849(2) 39(1) C(8) 332(2) -4338(2) -3532(1) 35(1) C(9) 440(2) -4622(2) -2685(1) 31(1) C(10) 1415(2) -4683(2) -2129(1) 26(1) C(11) 1525(2) -5023(2) -1187(1) 27(1) C(12) 573(2) -5715(2) -1035(1) 32(1) C(13) -173(2) -6273(3) -890(2) 40(1) C(14) 1728(2) -3629(2) -661(1) 25(1) C(15) 2500(2) -3560(2) 76(1) 28(1) C(16) 2662(2) -2315(2) 555(1) 28(1) C(17) 2066(1) -1085(2) 318(1) 25(1) C(18) 1300(2) -1154(2) -427(1) 26(1) C(19) 1138(2) -2413(2) -900(1) 26(1) C(20) 2227(2) -120(3) 1716(1) 41(1) C(21) 2493(2) 1219(3) 2238(2) 52(1) C(22) 1904(2) 2698(3) 1091(2) 42(1) C(23) 1620(2) 1425(2) 513(1) 32(1) ________________________________________________________________ Table 3. Bond lengths [A] and angles [deg] for ?. _____________________________________________________________ O(1)-C(1) 1.424(3) O(1)-C(4) 1.428(3) O(2)-C(11) 1.436(2) O(2)-H(2O) 1.02(3) O(3)-C(21) 1.420(3) O(3)-C(22) 1.440(3) N(1)-C(5) 1.462(2) N(1)-C(3) 1.474(3) N(1)-C(2) 1.477(3) N(1)-H(2O) 1.74(3) N(2)-C(17) 1.421(3) N(2)-C(23) 1.464(3) N(2)-C(20) 1.471(3) C(1)-C(2) 1.504(3) C(1)-H(1A) 1.00(2) C(1)-H(1B) 1.03(3) C(2)-H(2A) 1.04(2) C(2)-H(2B) 1.02(2) C(3)-C(4) 1.510(3) C(3)-H(3A) 1.03(2) C(3)-H(3B) 1.01(2) C(4)-H(4A) 1.05(2) C(4)-H(4B) 1.00(2) C(5)-C(6) 1.388(3) C(5)-C(10) 1.399(3) C(6)-C(7) 1.384(3) C(6)-H(6) 1.02(2) C(7)-C(8) 1.381(3) C(7)-H(7) 0.95(2) C(8)-C(9) 1.378(3) C(8)-H(8) 0.99(2) C(9)-C(10) 1.399(3) C(9)-H(9) 0.93(2) C(10)-C(11) 1.539(3) C(11)-C(12) 1.480(3) C(11)-C(14) 1.543(3) C(12)-C(13) 1.182(3) C(13)-H(13) 0.95(2) C(14)-C(19) 1.379(3) C(14)-C(15) 1.392(3) C(15)-C(16) 1.386(3) C(15)-H(15) 0.92(2) C(16)-C(17) 1.393(3) C(16)-H(16) 0.976(19) C(17)-C(18) 1.396(3) C(18)-C(19) 1.391(3) C(18)-H(18) 0.97(2) C(19)-H(19) 0.97(2) C(20)-C(21) 1.504(3) C(20)-H(20A) 0.99(2) C(20)-H(20B) 1.03(2) C(21)-H(21A) 0.98(3) C(21)-H(21B) 1.03(2) C(22)-C(23) 1.507(3) C(22)-H(22A) 1.01(2) C(22)-H(22B) 0.98(3) C(23)-H(23A) 0.94(2) C(23)-H(23B) 1.04(2) C(1)-O(1)-C(4) 110.54(18) C(11)-O(2)-H(2O) 97.8(18) C(21)-O(3)-C(22) 107.7(2) C(5)-N(1)-C(3) 112.67(16) C(5)-N(1)-C(2) 112.70(16) C(3)-N(1)-C(2) 108.81(16) C(5)-N(1)-H(2O) 93.8(10) C(3)-N(1)-H(2O) 122.5(11) C(2)-N(1)-H(2O) 105.6(10) C(17)-N(2)-C(23) 115.83(16) C(17)-N(2)-C(20) 112.83(16) C(23)-N(2)-C(20) 110.88(18) O(1)-C(1)-C(2) 111.09(19) O(1)-C(1)-H(1A) 108.3(13) C(2)-C(1)-H(1A) 110.3(12) O(1)-C(1)-H(1B) 107.5(13) C(2)-C(1)-H(1B) 108.1(14) H(1A)-C(1)-H(1B) 111.6(19) N(1)-C(2)-C(1) 109.60(19) N(1)-C(2)-H(2A) 108.5(12) C(1)-C(2)-H(2A) 110.0(12) N(1)-C(2)-H(2B) 109.7(12) C(1)-C(2)-H(2B) 108.1(12) H(2A)-C(2)-H(2B) 110.9(18) N(1)-C(3)-C(4) 109.00(19) N(1)-C(3)-H(3A) 107.9(11) C(4)-C(3)-H(3A) 110.8(11) N(1)-C(3)-H(3B) 110.4(12) C(4)-C(3)-H(3B) 109.9(11) H(3A)-C(3)-H(3B) 108.8(16) O(1)-C(4)-C(3) 111.8(2) O(1)-C(4)-H(4A) 106.8(12) C(3)-C(4)-H(4A) 112.3(12) O(1)-C(4)-H(4B) 107.1(13) C(3)-C(4)-H(4B) 110.3(14) H(4A)-C(4)-H(4B) 108.3(18) C(6)-C(5)-C(10) 120.58(19) C(6)-C(5)-N(1) 120.53(18) C(10)-C(5)-N(1) 118.88(18) C(7)-C(6)-C(5) 120.6(2) C(7)-C(6)-H(6) 118.9(12) C(5)-C(6)-H(6) 120.5(12) C(8)-C(7)-C(6) 119.7(2) C(8)-C(7)-H(7) 120.2(12) C(6)-C(7)-H(7) 120.1(12) C(9)-C(8)-C(7) 119.7(2) C(9)-C(8)-H(8) 118.5(11) C(7)-C(8)-H(8) 121.6(11) C(8)-C(9)-C(10) 122.0(2) C(8)-C(9)-H(9) 121.7(13) C(10)-C(9)-H(9) 116.3(13) C(5)-C(10)-C(9) 117.39(19) C(5)-C(10)-C(11) 121.14(17) C(9)-C(10)-C(11) 121.47(18) O(2)-C(11)-C(12) 105.23(16) O(2)-C(11)-C(10) 110.57(15) C(12)-C(11)-C(10) 111.00(16) O(2)-C(11)-C(14) 110.92(16) C(12)-C(11)-C(14) 108.80(16) C(10)-C(11)-C(14) 110.21(16) C(13)-C(12)-C(11) 178.1(2) C(12)-C(13)-H(13) 178.9(13) C(19)-C(14)-C(15) 117.65(19) C(19)-C(14)-C(11) 121.02(17) C(15)-C(14)-C(11) 121.32(18) C(16)-C(15)-C(14) 121.0(2) C(16)-C(15)-H(15) 120.0(12) C(14)-C(15)-H(15) 119.0(12) C(15)-C(16)-C(17) 121.5(2) C(15)-C(16)-H(16) 120.2(11) C(17)-C(16)-H(16) 118.2(11) C(16)-C(17)-C(18) 117.25(19) C(16)-C(17)-N(2) 119.71(17) C(18)-C(17)-N(2) 123.04(18) C(19)-C(18)-C(17) 120.8(2) C(19)-C(18)-H(18) 118.1(12) C(17)-C(18)-H(18) 121.2(12) C(14)-C(19)-C(18) 121.78(19) C(14)-C(19)-H(19) 119.2(12) C(18)-C(19)-H(19) 118.9(12) N(2)-C(20)-C(21) 110.4(2) N(2)-C(20)-H(20A) 109.2(13) C(21)-C(20)-H(20A) 108.0(13) N(2)-C(20)-H(20B) 111.2(11) C(21)-C(20)-H(20B) 107.1(12) H(20A)-C(20)-H(20B) 111.0(19) O(3)-C(21)-C(20) 111.9(2) O(3)-C(21)-H(21A) 106.2(14) C(20)-C(21)-H(21A) 108.5(14) O(3)-C(21)-H(21B) 109.0(14) C(20)-C(21)-H(21B) 108.9(14) H(21A)-C(21)-H(21B) 112.3(19) O(3)-C(22)-C(23) 111.2(2) O(3)-C(22)-H(22A) 108.2(12) C(23)-C(22)-H(22A) 110.7(13) O(3)-C(22)-H(22B) 108.7(14) C(23)-C(22)-H(22B) 107.4(14) H(22A)-C(22)-H(22B) 110.7(19) N(2)-C(23)-C(22) 111.37(18) N(2)-C(23)-H(23A) 109.7(13) C(22)-C(23)-H(23A) 109.1(12) N(2)-C(23)-H(23B) 110.7(11) C(22)-C(23)-H(23B) 107.3(11) H(23A)-C(23)-H(23B) 108.6(17) _____________________________________________________________ Symmetry transformations used to generate equivalent atoms: Table 4. Anisotropic displacement parameters (A^2 x 10^3) for ?. 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) 30(1) 46(1) 66(1) 5(1) 1(1) -3(1) O(2) 37(1) 26(1) 33(1) 4(1) 10(1) 6(1) O(3) 53(1) 47(1) 42(1) -16(1) -3(1) 16(1) N(1) 25(1) 26(1) 31(1) 0(1) 6(1) 0(1) N(2) 31(1) 25(1) 28(1) -1(1) 4(1) 3(1) C(1) 32(1) 39(2) 49(2) 3(1) 2(1) 4(1) C(2) 31(1) 33(1) 37(1) 1(1) 8(1) 5(1) C(3) 37(1) 30(1) 43(2) -1(1) 6(1) -2(1) C(4) 40(1) 36(2) 53(2) -6(1) -3(1) -7(1) C(5) 28(1) 24(1) 28(1) -1(1) 6(1) 4(1) C(6) 37(1) 29(1) 32(1) 4(1) 11(1) 7(1) C(7) 47(1) 41(1) 26(1) 3(1) 5(1) 12(1) C(8) 34(1) 34(1) 32(1) -4(1) -3(1) 9(1) C(9) 31(1) 25(1) 38(1) -4(1) 8(1) 3(1) C(10) 29(1) 20(1) 28(1) -4(1) 7(1) 4(1) C(11) 27(1) 25(1) 31(1) 0(1) 8(1) 1(1) C(12) 37(1) 28(1) 31(1) -2(1) 11(1) 0(1) C(13) 39(1) 39(2) 44(2) 2(1) 13(1) -3(1) C(14) 26(1) 25(1) 25(1) 2(1) 9(1) 0(1) C(15) 26(1) 24(1) 34(1) 3(1) 6(1) 4(1) C(16) 23(1) 29(1) 29(1) 1(1) 2(1) 1(1) C(17) 24(1) 26(1) 25(1) 0(1) 7(1) -2(1) C(18) 30(1) 24(1) 24(1) 6(1) 6(1) 5(1) C(19) 28(1) 27(1) 22(1) 0(1) 4(1) 0(1) C(20) 56(2) 36(2) 27(1) -4(1) 3(1) 7(1) C(21) 63(2) 52(2) 35(2) -10(1) -3(1) 18(2) C(22) 40(1) 35(2) 49(2) -6(1) 3(1) 4(1) C(23) 31(1) 28(1) 34(1) 0(1) 3(1) 3(1) _______________________________________________________________________ Table 5. Hydrogen coordinates ( x 10^4) and isotropic displacement parameters (A^2 x 10^3) for ?. ________________________________________________________________ x y z U(iso) ________________________________________________________________ H(2O) 2900(2) -5570(4) -1160(2) 108(12) H(1A) 4938(16) -6030(2) -1085(15) 40(6) H(1B) 5553(19) -6160(3) -1883(16) 55(7) H(2A) 4164(17) -4960(2) -2797(14) 48(7) H(2B) 3730(16) -6430(2) -2372(13) 40(6) H(3A) 3306(16) -2480(2) -1444(12) 30(5) H(3B) 3919(15) -2610(2) -2224(13) 33(6) H(4A) 5224(17) -2300(3) -921(13) 44(6) H(4B) 4719(18) -3730(3) -548(16) 54(7) H(6) 2814(16) -3900(2) -3553(13) 38(6) H(7) 1136(15) -3900(2) -4432(14) 37(6) H(8) -366(16) -4410(2) -3904(12) 29(5) H(9) -131(17) -4790(2) -2452(13) 39(6) H(13) -782(18) -6710(2) -782(14) 45(7) H(15) 2897(15) -4360(2) 248(12) 28(6) H(16) 3189(15) -2290(2) 1081(12) 27(5) H(18) 850(16) -340(2) -622(12) 36(6) H(19) 572(16) -2450(2) -1394(13) 34(6) H(20A) 2751(18) -860(3) 1945(15) 51(7) H(20B) 1493(18) -440(2) 1772(13) 39(6) H(21A) 2414(18) 1020(3) 2809(17) 54(7) H(21B) 3242(19) 1530(3) 2223(14) 53(7) H(22A) 2648(18) 3000(2) 1119(13) 47(6) H(22B) 1420(19) 3480(3) 867(15) 57(8) H(23A) 913(17) 1210(2) 462(12) 29(6) H(23B) 1733(15) 1720(2) -74(14) 35(6) ________________________________________________________________