Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK

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Small Molecule Crystallography Lab Department of Chemistry and Biochemistry University of Oklahoma 101 Stephenson Parkway Norman, OK 73019-5251 Sample: KP-XI-cinnamyl-chiral alcohol Lab ID: 12040 User: Kaushik Panigrahi Formula: C 14 H 19 F 2 O 4 P Date: May 11, 2012 For Prof. David Berkowitz

Table of Contents Figure 1. Thermal Ellipsoid Plot of Orientation A.. 3 Figure 2. Thermal Ellipsoid Plot of Orientation B.. 4 Figure 3. Packing Diagram 5 Comments.. 6 Experimental.. 6 Acknowledgements... 7 References. 7 Table 1. Crystal Data 8 Table 2. Atom Coordinates 9 Table 3. Bond Distances and Angles 10 Table 4. Anisotropic Displacement Parameters.. 12 Table 5. Hydrogen Atom Parameters 13 Table 6. Torsion Angles.. 14 Table 7. Hydrogen Bond Details 15 KP-XI-cinnamyl-chiral alcohol 12040 Page 2

KP-XI-cinnamyl-chiral alcohol 12040 Page 3

KP-XI-cinnamyl-chiral alcohol 12040 Page 4

KP-XI-cinnamyl-chiral alcohol 12040 Page 5

Comment The crystal structure exhibited disorder at atoms C4 and atoms C7 C14. The occupancies of C4 refined to 0.579(7) and 0.421(7) for the unprimed and primed atoms. The occupancies of C7 C14 refined to 0.504(3) and 0.496(3) for the unprimed and primed atoms. Restraints on the positional parameters of atoms C7 C14 were required. The displacement parameters of C4 and C4 were constrained to be equal. The displacement ellipsoids were drawn at the 50% probability level. Experimental A colorless block-shaped crystal of dimensions 0.40 x 0.38 x 0.32 mm was selected for structural analysis. Intensity data for this compound were collected using a diffractometer with a Bruker APEX ccd area detector (1) and graphite-monochromated Mo K radiation ( = 0.71073 Å). The sample was cooled to 100(2) K. Cell parameters were determined from a non-linear least squares fit of 5360 peaks in the range 2.48 < < 28.31. A total of 7836 data were measured in the range 1.63 < < 28.31 using and oscillation frames. The data were corrected for absorption by the empirical method (2) giving minimum and maximum transmission factors of 0.9213 and 0.9363. The data were merged to form a set of 3886 independent data with R(int) = 0.0207 and a coverage of 99.9 %. The monoclinic space group C2 was determined by systematic absences and statistical tests and verified by subsequent refinement. The structure was solved by direct methods and refined by full-matrix least-squares methods on F 2 (3). The positions of hydrogens bonded to carbons were initially determined by geometry and were refined with a riding model. The hydrogen bonded to O4 was located on a difference map, and its position was refined independently. Non-hydrogen atoms were refined with anisotropic displacement parameters. Hydrogen atom displacement parameters were set to 1.2 (1.5 for methyl) times the isotropic equivalent displacement parameters of the bonded atoms. A total of 268 parameters were refined against 144 restraints and 3886 data to give wr(f 2 ) = 0.0940 and S = 0.988 for weights of w = 1/[ 2 (F 2 ) + (0.0580 P) 2 + 0.4000 P], where P = [F o 2 + 2F c 2 ] / 3. The final R(F) was 0.0373 for the 3623 observed, [F > 4 (F)], data. The largest shift/s.u. was 0.000 in the final refinement cycle. The final difference map had maxima and minima of 0.275 and -0.196 e/å 3, respectively. The absolute structure was determined by refinement of the Flack parameter(4). KP-XI-cinnamyl-chiral alcohol 12040 Page 6

The polar axis restraint was taken from Flack and Schwarzenbach(5). Acknowledgment The authors thank the National Science Foundation (grant CHE-0130835) and the University of Oklahoma for funds to purchase of the X-ray instrument and computers. This structure was determined by Douglas R. Powell. References (1) (a) Data Collection: SMART Software Reference Manual (2007). Bruker-AXS, 5465 E. Cheryl Parkway, Madison, WI 53711-5373 USA. (b) Data Reduction: SAINT Software Reference Manual (2007). Bruker-AXS, 5465 E. Cheryl Parkway, Madison, WI 53711-5373 USA. (2) G. M. Sheldrick (2001). SADABS. Program for Empirical Absorption Correction of Area Detector Data. University of Göttingen, Germany. (3) G. M. Sheldrick (2008). Acta Cryst., A64, 112-122. (4) H. D. Flack (1983). Acta Cryst. A39, 876-881. (5) H. D. Flack and D. Schwarzenbach (1988). Acta Cryst. A44, 499-506. KP-XI-cinnamyl-chiral alcohol 12040 Page 7

Table 1. Crystal data and structure refinement for 12040. Empirical formula Formula weight 320.26 Crystal system Space group C 14 H 19 F 2 O 4 P monoclinic Unit cell dimensions a = 25.005(3) Å = 90 C2 Volume 1565.6(3) Å 3 Z, Z' 4, 1 Density (calculated) 1.359 Mg/m 3 Wavelength Temperature F(000) 672 b = 5.7568(7) Å = 90.027(2) c = 10.8764(13) Å = 90 0.71073 Å 100(2) K Absorption coefficient 0.208 mm -1 Absorption correction Semi-empirical from equivalents Max. and min. transmission 0.9363 and 0.9213 Theta range for data collection 1.63 to 28.31 Reflections collected 7836 Independent reflections 3886 [R(int) = 0.0207] Data / restraints / parameters 3886 / 144 / 268 wr(f 2 all data) wr2 = 0.0940 R(F obsd data) R1 = 0.0373 Goodness-of-fit on F 2 0.988 Observed data [I > 2 (I)] 3623 Absolute structure parameter 0.13(9) Largest and mean shift / s.u. 0.000and 0.000 Largest diff. peak and hole 0.275 and -0.196 e/å 3 ---------- wr2 = { [w(f 2 o - F 2 c ) 2 ] / [w(f 2 o ) 2 ] } 1/2 R1 = F o - F c / F o KP-XI-cinnamyl-chiral alcohol 12040 Page 8

Table 2. Atomic coordinates and equivalent isotropic displacement parameters for 12040. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) P(1) 0.173407(15) 0.84752(9) 0.72442(4) 0.02129(11) F(1) 0.23270(5) 0.5908(2) 0.87094(10) 0.0369(3) F(2) 0.27183(4) 0.9011(2) 0.80014(12) 0.0424(3) O(1) 0.17848(6) 1.0449(2) 0.64082(13) 0.0340(3) O(2) 0.14608(5) 0.8972(2) 0.85115(12) 0.0273(3) O(3) 0.14003(5) 0.6338(2) 0.68143(12) 0.0271(3) O(4) 0.26425(6) 0.7009(3) 0.56060(14) 0.0365(3) C(1) 0.16229(9) 1.0962(4) 0.9258(2) 0.0429(5) C(2) 0.11677(13) 1.2577(5) 0.9403(3) 0.0628(8) C(3) 0.12817(8) 0.5877(5) 0.55205(18) 0.0384(5) C(4) 0.08036(19) 0.4234(12) 0.5455(5) 0.0461(12) C(4') 0.0713(3) 0.5458(17) 0.5419(7) 0.0461(12) C(5) 0.23889(7) 0.7220(3) 0.76684(16) 0.0248(4) C(6) 0.26563(7) 0.5712(3) 0.66878(17) 0.0263(4) C(7) 0.31520(12) 0.4505(7) 0.7210(3) 0.0208(8) C(8) 0.36324(12) 0.5105(6) 0.6811(3) 0.0223(8) C(9) 0.41446(12) 0.4118(4) 0.7260(2) 0.0202(8) C(10) 0.46223(12) 0.4987(6) 0.6801(4) 0.0355(10) C(11) 0.51090(13) 0.4131(7) 0.7199(4) 0.0438(13) C(12) 0.51262(19) 0.2379(9) 0.8067(6) 0.0351(19) C(13) 0.46530(16) 0.1469(9) 0.8525(5) 0.0327(13) C(14) 0.41664(10) 0.2331(5) 0.8117(3) 0.0297(10) C(7') 0.32577(10) 0.5614(5) 0.6948(3) 0.0235(8) C(8') 0.34776(12) 0.3656(7) 0.7325(3) 0.0246(8) C(9') 0.40482(12) 0.3302(7) 0.7662(2) 0.0229(8) C(10') 0.44217(13) 0.5081(6) 0.7637(3) 0.0328(10) C(11') 0.49514(14) 0.4661(7) 0.7964(4) 0.0385(11) C(12') 0.5111(2) 0.2470(8) 0.8320(6) 0.0312(17) C(13') 0.47410(17) 0.0673(8) 0.8342(5) 0.0345(14) C(14') 0.42145(14) 0.1099(7) 0.8012(3) 0.0287(10) KP-XI-cinnamyl-chiral alcohol 12040 Page 9

Table 3. Bond lengths [Å] and angles [ ] for 12040. P(1)-O(1) 1.4609(14) P(1)-O(3) 1.5582(14) P(1)-O(2) 1.5651(13) P(1)-C(5) 1.8480(17) F(1)-C(5) 1.370(2) F(2)-C(5) 1.368(2) O(2)-C(1) 1.462(3) O(3)-C(3) 1.462(2) O(4)-C(6) 1.394(2) O(4)-H(4) 0.74(3) C(1)-C(2) 1.478(4) C(1)-H(1A) 0.9900 C(1)-H(1B) 0.9900 C(2)-H(2A) 0.9800 C(2)-H(2B) 0.9800 C(2)-H(2C) 0.9800 C(3)-C(4') 1.447(7) C(3)-C(4) 1.526(6) C(3)-H(3A) 0.9900 C(3)-H(3B) 0.9900 C(4)-H(4A) 0.9800 C(4)-H(4B) 0.9800 C(4)-H(4C) 0.9800 C(4')-H(4D) 0.9800 C(4')-H(4E) 0.9800 C(4')-H(4F) 0.9800 C(5)-C(6) 1.529(2) C(6)-C(7) 1.530(3) C(6)-C(7') 1.531(3) C(6)-H(6) 1.0000 C(6)-H(6') 1.0000 O(1)-P(1)-O(3) 118.29(8) O(1)-P(1)-O(2) 116.36(8) O(3)-P(1)-O(2) 100.05(7) O(1)-P(1)-C(5) 112.48(9) O(3)-P(1)-C(5) 103.92(8) O(2)-P(1)-C(5) 103.82(8) C(1)-O(2)-P(1) 120.76(13) C(3)-O(3)-P(1) 122.72(13) C(6)-O(4)-H(4) 109(2) O(2)-C(1)-C(2) 109.8(2) C(7)-C(8) 1.324(4) C(7)-H(7) 0.9500 C(8)-C(9) 1.484(4) C(8)-H(8) 0.9500 C(9)-C(10) 1.388(3) C(9)-C(14) 1.389(3) C(10)-C(11) 1.382(3) C(10)-H(10) 0.9500 C(11)-C(12) 1.382(4) C(11)-H(11) 0.9500 C(12)-C(13) 1.387(4) C(12)-H(12) 0.9500 C(13)-C(14) 1.387(3) C(13)-H(13) 0.9500 C(14)-H(14) 0.9500 C(7')-C(8') 1.319(4) C(7')-H(7') 0.9500 C(8')-C(9') 1.487(4) C(8')-H(8') 0.9500 C(9')-C(10') 1.387(3) C(9')-C(14') 1.388(4) C(10')-C(11') 1.393(3) C(10')-H(10') 0.9500 C(11')-C(12') 1.379(4) C(11')-H(11') 0.9500 C(12')-C(13') 1.388(4) C(12')-H(12') 0.9500 C(13')-C(14') 1.386(4) C(13')-H(13') 0.9500 C(14')-H(14') 0.9500 O(2)-C(1)-H(1A) 109.7 C(2)-C(1)-H(1A) 109.7 O(2)-C(1)-H(1B) 109.7 C(2)-C(1)-H(1B) 109.7 H(1A)-C(1)-H(1B) 108.2 C(1)-C(2)-H(2A) 109.5 C(1)-C(2)-H(2B) 109.5 H(2A)-C(2)-H(2B) 109.5 C(1)-C(2)-H(2C) 109.5 H(2A)-C(2)-H(2C) 109.5 KP-XI-cinnamyl-chiral alcohol 12040 Page 10

H(2B)-C(2)-H(2C) 109.5 C(4')-C(3)-O(3) 107.6(3) O(3)-C(3)-C(4) 108.4(2) O(3)-C(3)-H(3A) 110.0 C(4)-C(3)-H(3A) 110.0 O(3)-C(3)-H(3B) 110.0 C(4)-C(3)-H(3B) 110.0 H(3A)-C(3)-H(3B) 108.4 C(3)-C(4)-H(4A) 109.5 C(3)-C(4)-H(4B) 109.5 H(4A)-C(4)-H(4B) 109.5 C(3)-C(4)-H(4C) 109.5 H(4A)-C(4)-H(4C) 109.5 H(4B)-C(4)-H(4C) 109.5 C(3)-C(4')-H(4D) 109.5 C(3)-C(4')-H(4E) 109.5 H(4D)-C(4')-H(4E) 109.5 C(3)-C(4')-H(4F) 109.5 H(4D)-C(4')-H(4F) 109.5 H(4E)-C(4')-H(4F) 109.5 F(2)-C(5)-F(1) 105.35(14) F(2)-C(5)-C(6) 110.42(14) F(1)-C(5)-C(6) 108.26(16) F(2)-C(5)-P(1) 107.74(13) F(1)-C(5)-P(1) 108.75(11) C(6)-C(5)-P(1) 115.82(12) O(4)-C(6)-C(5) 105.92(15) O(4)-C(6)-C(7) 125.2(2) C(5)-C(6)-C(7) 110.69(18) O(4)-C(6)-C(7') 101.53(17) C(5)-C(6)-C(7') 108.77(17) O(4)-C(6)-H(6) 104.4 C(5)-C(6)-H(6) 104.4 C(7)-C(6)-H(6) 104.4 O(4)-C(6)-H(6') 113.3 C(5)-C(6)-H(6') 113.3 C(7')-C(6)-H(6') 113.3 C(8)-C(7)-C(6) 119.6(3) C(8)-C(7)-H(7) 120.2 C(6)-C(7)-H(7) 120.2 C(7)-C(8)-C(9) 125.1(3) C(7)-C(8)-H(8) 117.4 C(9)-C(8)-H(8) 117.4 C(10)-C(9)-C(14) 118.3(3) C(10)-C(9)-C(8) 119.1(3) C(14)-C(9)-C(8) 122.6(3) C(11)-C(10)-C(9) 121.1(3) C(11)-C(10)-H(10) 119.5 C(9)-C(10)-H(10) 119.5 C(12)-C(11)-C(10) 120.1(3) C(12)-C(11)-H(11) 120.0 C(10)-C(11)-H(11) 120.0 C(11)-C(12)-C(13) 119.7(4) C(11)-C(12)-H(12) 120.2 C(13)-C(12)-H(12) 120.2 C(12)-C(13)-C(14) 119.9(4) C(12)-C(13)-H(13) 120.1 C(14)-C(13)-H(13) 120.1 C(13)-C(14)-C(9) 120.9(3) C(13)-C(14)-H(14) 119.5 C(9)-C(14)-H(14) 119.5 C(8')-C(7')-C(6) 119.9(3) C(8')-C(7')-H(7') 120.1 C(6)-C(7')-H(7') 120.1 C(7')-C(8')-C(9') 126.4(3) C(7')-C(8')-H(8') 116.8 C(9')-C(8')-H(8') 116.8 C(10')-C(9')-C(14') 118.6(3) C(10')-C(9')-C(8') 122.7(3) C(14')-C(9')-C(8') 118.7(3) C(9')-C(10')-C(11') 120.5(3) C(9')-C(10')-H(10') 119.8 C(11')-C(10')-H(10') 119.8 C(12')-C(11')-C(10') 120.4(3) C(12')-C(11')-H(11') 119.8 C(10')-C(11')-H(11') 119.8 C(11')-C(12')-C(13') 119.5(4) C(11')-C(12')-H(12') 120.2 C(13')-C(12')-H(12') 120.2 C(14')-C(13')-C(12') 119.8(4) C(14')-C(13')-H(13') 120.1 C(12')-C(13')-H(13') 120.1 C(13')-C(14')-C(9') 121.1(3) C(13')-C(14')-H(14') 119.4 C(9')-C(14')-H(14') 119.4 KP-XI-cinnamyl-chiral alcohol 12040 Page 11

Table 4. Anisotropic displacement parameters (Å 2 x 10 3 ) for 12040. The anisotropic displacement factor exponent takes the form: -2 2 [ h 2 a* 2 U 11 +... + 2 h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 P(1) 19(1) 23(1) 22(1) 1(1) 4(1) 3(1) F(1) 39(1) 51(1) 21(1) 2(1) -4(1) 16(1) F(2) 24(1) 55(1) 48(1) -28(1) 4(1) -11(1) O(1) 43(1) 28(1) 31(1) 7(1) 11(1) 8(1) O(2) 25(1) 32(1) 24(1) -4(1) 5(1) 1(1) O(3) 23(1) 36(1) 22(1) -1(1) -4(1) -2(1) O(4) 51(1) 29(1) 29(1) -2(1) 17(1) 6(1) C(1) 47(1) 44(1) 38(1) -17(1) 10(1) -5(1) C(2) 76(2) 43(1) 70(2) -11(1) 34(2) 11(1) C(3) 31(1) 62(1) 22(1) -5(1) -4(1) -6(1) C(4) 27(2) 77(4) 35(1) -16(3) -6(1) -5(2) C(4') 27(2) 77(4) 35(1) -16(3) -6(1) -5(2) C(5) 18(1) 32(1) 24(1) -6(1) -2(1) 1(1) C(6) 20(1) 33(1) 26(1) -6(1) -5(1) 6(1) C(7) 18(2) 19(2) 26(2) 2(1) 0(1) 1(2) C(8) 21(2) 21(2) 25(2) 3(1) 1(1) 2(1) C(9) 17(2) 18(2) 25(2) 2(2) 0(2) 0(1) C(10) 21(2) 33(2) 53(3) 18(2) 6(2) 4(2) C(11) 21(2) 45(3) 66(3) 22(2) 7(2) 3(2) C(12) 20(3) 47(4) 39(3) 3(2) -3(2) 2(3) C(13) 28(2) 35(3) 35(3) 11(2) -2(2) 5(2) C(14) 17(2) 34(3) 38(3) 17(2) 1(2) -1(2) C(7') 21(2) 26(2) 24(2) -2(2) 0(1) 0(2) C(8') 21(2) 29(2) 24(2) -5(2) -1(1) 1(2) C(9') 20(2) 29(2) 19(2) 1(2) 2(2) 1(2) C(10') 29(2) 32(2) 37(2) 2(2) -2(2) 7(2) C(11') 23(2) 51(3) 42(3) 4(2) -5(2) -4(2) C(12') 22(3) 41(4) 31(3) 6(2) 1(2) 11(3) C(13') 29(2) 43(3) 32(3) 6(2) -3(2) 12(2) C(14') 30(2) 32(2) 25(2) 7(2) -1(2) 8(2) KP-XI-cinnamyl-chiral alcohol 12040 Page 12

Table 5. Hydrogen coordinates and isotropic displacement parameters for 12040. x y z U(eq) H(4) 0.2769(10) 0.632(5) 0.511(3) 0.044 H(1A) 0.1925 1.1775 0.8857 0.051 H(1B) 0.1744 1.0421 1.0076 0.051 H(2A) 0.1070 1.3220 0.8599 0.094 H(2B) 0.1270 1.3843 0.9958 0.094 H(2C) 0.0861 1.1739 0.9748 0.094 H(3A) 0.1596 0.5160 0.5117 0.046 H(3B) 0.1198 0.7348 0.5090 0.046 H(4A) 0.0500 0.4924 0.5892 0.069 H(4B) 0.0898 0.2748 0.5838 0.069 H(4C) 0.0706 0.3975 0.4593 0.069 H(4D) 0.0619 0.4051 0.5878 0.069 H(4E) 0.0617 0.5255 0.4552 0.069 H(4F) 0.0517 0.6785 0.5758 0.069 H(6) 0.2396 0.4422 0.6542 0.032 H(6') 0.2489 0.4143 0.6602 0.032 H(7) 0.3115 0.3331 0.7818 0.025 H(8) 0.3651 0.6257 0.6187 0.027 H(10) 0.4615 0.6189 0.6203 0.043 H(11) 0.5432 0.4748 0.6876 0.053 H(12) 0.5460 0.1801 0.8348 0.042 H(13) 0.4662 0.0257 0.9117 0.039 H(14) 0.3844 0.1690 0.8427 0.036 H(7') 0.3472 0.6960 0.6839 0.028 H(8') 0.3249 0.2343 0.7386 0.030 H(10') 0.4315 0.6598 0.7394 0.039 H(11') 0.5204 0.5893 0.7943 0.046 H(12') 0.5472 0.2191 0.8549 0.037 H(13') 0.4848-0.0843 0.8583 0.041 H(14') 0.3963-0.0138 0.8026 0.034 KP-XI-cinnamyl-chiral alcohol 12040 Page 13

Table 6. Torsion angles [ ] for 12040. O(1)-P(1)-O(2)-C(1) -48.01(17) O(3)-P(1)-O(2)-C(1) -176.69(15) C(5)-P(1)-O(2)-C(1) 76.15(16) O(1)-P(1)-O(3)-C(3) 19.99(17) O(2)-P(1)-O(3)-C(3) 147.40(15) C(5)-P(1)-O(3)-C(3) -105.52(15) P(1)-O(2)-C(1)-C(2) 117.40(19) P(1)-O(3)-C(3)-C(4') -130.2(4) P(1)-O(3)-C(3)-C(4) -160.4(3) O(1)-P(1)-C(5)-F(2) 47.88(14) O(3)-P(1)-C(5)-F(2) 177.01(11) O(2)-P(1)-C(5)-F(2) -78.75(13) O(1)-P(1)-C(5)-F(1) 161.59(12) O(3)-P(1)-C(5)-F(1) -69.28(13) O(2)-P(1)-C(5)-F(1) 34.96(14) O(1)-P(1)-C(5)-C(6) -76.28(16) O(3)-P(1)-C(5)-C(6) 52.84(16) O(2)-P(1)-C(5)-C(6) 157.08(14) F(2)-C(5)-C(6)-O(4) -73.16(18) F(1)-C(5)-C(6)-O(4) 171.99(14) P(1)-C(5)-C(6)-O(4) 49.60(18) F(2)-C(5)-C(6)-C(7) 65.3(2) F(1)-C(5)-C(6)-C(7) -49.6(2) P(1)-C(5)-C(6)-C(7) -171.96(19) F(2)-C(5)-C(6)-C(7') 35.3(2) F(1)-C(5)-C(6)-C(7') -79.6(2) P(1)-C(5)-C(6)-C(7') 158.05(16) O(4)-C(6)-C(7)-C(8) 16.8(4) C(5)-C(6)-C(7)-C(8) -111.9(3) C(6)-C(7)-C(8)-C(9) 178.4(2) C(7)-C(8)-C(9)-C(10) -177.0(4) C(7)-C(8)-C(9)-C(14) 3.8(4) C(14)-C(9)-C(10)-C(11) -1.2(4) C(8)-C(9)-C(10)-C(11) 179.6(3) C(9)-C(10)-C(11)-C(12) 0.1(6) C(10)-C(11)-C(12)-C(13) 0.7(8) C(11)-C(12)-C(13)-C(14) -0.4(8) C(12)-C(13)-C(14)-C(9) -0.7(6) C(10)-C(9)-C(14)-C(13) 1.5(4) C(8)-C(9)-C(14)-C(13) -179.3(3) O(4)-C(6)-C(7')-C(8') -137.9(3) C(5)-C(6)-C(7')-C(8') 110.7(3) C(6)-C(7')-C(8')-C(9') -177.41(19) C(7')-C(8')-C(9')-C(10') 1.3(3) C(7')-C(8')-C(9')-C(14') -178.5(3) C(14')-C(9')-C(10')-C(11') -0.4(4) C(8')-C(9')-C(10')-C(11') 179.8(2) C(9')-C(10')-C(11')-C(12') -0.1(6) C(10')-C(11')-C(12')-C(13') 0.4(8) C(11')-C(12')-C(13')-C(14') -0.3(8) C(12')-C(13')-C(14')-C(9') -0.2(6) C(10')-C(9')-C(14')-C(13') 0.6(5) C(8')-C(9')-C(14')-C(13') -179.7(3) KP-XI-cinnamyl-chiral alcohol 12040 Page 14

Table 7. Hydrogen bonds for 12040[Å and ]. D-H...A d(d-h) d(h...a) d(d...a) <(DHA) O(4)-H(4)...O(1)#1 0.74(3) 2.06(3) 2.768(2) 161(3) Symmetry transformations used to generate equivalent atoms: #1 -x+1/2, y-1/2, -z+1 KP-XI-cinnamyl-chiral alcohol 12040 Page 15

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