+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + SHELXL-97 - CRYSTAL STRUCTURE REFINEMENT - WinGX VERSION + + Copyright(C) George M. Sheldrick 1993-7 Release 97-2 + + shelxl started at 18:23:18 on 11-Nov-2010 + +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ TITL 2008lsh166 in P2(1)/n CELL 0.71073 4.7821 13.4170 13.9793 90.000 92.527 90.000 ZERR 4.00 0.0004 0.0016 0.0015 0.000 0.007 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O F UNIT 36 32 4 4 12 V = 896.06 F(000) = 416.0 Mu = 0.14 mm-1 Cell Wt = 812.66 Rho = 1.506 MERG 2 OMIT -3.00 55.00 OMIT 0 0 2 OMIT 0 2 0 FMAP 2 PLAN 5 ACTA DFIX 0.88 0.02 N1 H1N EQIV $1 x-1, y, z HTAB N1 O1_$1 HTAB N1 F3 HTAB SIZE 0.28 0.06 0.02 BOND $H L.S. 6 TEMP -153.00 WGHT 0.049600 0.605000 EXTI 0.033100 FVAR 0.83857 C1 1 0.561505 0.835795 0.041397 11.00000 0.01774 0.02699 = 0.02676 0.00084 0.00149 0.00246 C2 1 0.492897 0.738307 0.014082 11.00000 0.01979 0.02758 = 0.02952 0.00094 0.00139 -0.00091 C3 1 0.575747 0.701549 -0.073293 11.00000 0.03650 0.03149 = 0.03117 -0.00430 0.00337 -0.00117 AFIX 43 H3 2 0.528766 0.635327 -0.091911 11.00000 -1.20000 AFIX 0 C4 1 0.726564 0.761303 -0.133182 11.00000 0.04386 0.03741 = 0.02783 -0.00125 0.00971 0.00175 AFIX 43 H4 2 0.780123 0.736314 -0.193267 11.00000 -1.20000 AFIX 0 C5 1 0.799291 0.856932 -0.105933 11.00000 0.03603 0.03433 = 0.03241 0.00594 0.01016 0.00011 AFIX 43 H5 2 0.906243 0.897212 -0.146601 11.00000 -1.20000 AFIX 0 C6 1 0.716340 0.894320 -0.019176 11.00000 0.02397 0.02773 = 0.03548 0.00201 0.00424 -0.00038 AFIX 43 H6 2 0.765608 0.960447 -0.000920 11.00000 -1.20000 AFIX 0 C7 1 0.657852 0.920924 0.194089 11.00000 0.01813 0.02702 = 0.03251 0.00114 0.00153 0.00092 C8 1 0.531539 0.970455 0.277814 11.00000 0.02255 0.03709 = 0.03489 -0.00738 0.00128 -0.00106 AFIX 137 H8A 2 0.598834 0.937670 0.337100 11.00000 -1.50000 H8B 2 0.327148 0.965260 0.271495 11.00000 -1.50000 H8C 2 0.585904 1.040876 0.279687 11.00000 -1.50000 AFIX 0 C9 1 0.342907 0.671028 0.080051 11.00000 0.02761 0.02790 = 0.03407 -0.00145 0.00408 0.00068 N1 3 0.476451 0.876507 0.129896 11.00000 0.01555 0.02897 = 0.02871 -0.00361 0.00377 -0.00038 O1 4 0.912462 0.921250 0.184497 11.00000 0.01663 0.04342 = 0.04227 -0.00830 0.00272 0.00011 F1 5 0.495584 0.652665 0.161814 11.00000 0.03344 0.04893 = 0.03814 0.01541 0.00499 0.00677 F2 5 0.282275 0.581828 0.041484 11.00000 0.07056 0.03152 = 0.05230 -0.00880 0.02385 -0.01931 F3 5 0.100399 0.708971 0.108191 11.00000 0.02159 0.03845 = 0.04758 0.00436 0.00680 -0.00063 H1N 2 0.301431 0.879083 0.142204 11.00000 0.02961 HKLF 4 Covalent radii and connectivity table for 2008lsh166 in P2(1)/n C 0.770 H 0.320 N 0.700 O 0.660 F 0.640 C1 - C6 C2 N1 C2 - C3 C1 C9 C3 - C4 C2 C4 - C5 C3 C5 - C4 C6 C6 - C5 C1 C7 - O1 N1 C8 C8 - C7 C9 - F2 F3 F1 C2 N1 - C7 C1 O1 - C7 F1 - C9 F2 - C9 F3 - C9 Operators for generating equivalent atoms: $1 x-1, y, z 11785 Reflections read, of which 353 rejected -6 =< h =< 6, -17 =< k =< 17, -17 =< l =< 18, Max. 2-theta = 54.99 0 Systematic absence violations Inconsistent equivalents etc. h k l Fo^2 Sigma(Fo^2) N Esd of mean(Fo^2) -5 3 1 97.12 6.51 5 47.59 -4 6 3 12.09 0.82 6 4.36 -4 8 5 78.05 4.07 8 30.36 -3 11 5 62.74 4.36 7 38.54 -1 7 7 77.84 3.73 7 18.91 3 6 8 92.96 4.60 9 24.37 6 Inconsistent equivalents 2048 Unique reflections, of which 0 suppressed R(int) = 0.0906 R(sigma) = 0.0774 Friedel opposites merged Maximum memory for data reduction = 1378 / 20616 Default effective X-H distances for T = -153.0 C AFIX m = 1 2 3 4 4[N] 3[N] 15[B] 8[O] 9 9[N] 16 d(X-H) = 1.00 0.99 0.98 0.95 0.88 0.91 1.12 0.84 0.95 0.88 0.95 Note that these distances are chosen to give the best fit to the X-ray data and so avoid the introduction of systematic error. The true internuclear distances are longer and do not vary with temperature ! The apparent variation with temperature is caused by libration. Least-squares cycle 1 Maximum vector length = 511 Memory required = 1721 / 169120 wR2 = 0.1394 before cycle 1 for 2048 data and 133 / 133 parameters Summary of restraints applied in cycle 1 ANTIBUMP DFIX DANG SAME/SADI CHIV/Z CHIV/NZ FLAT DELU SIMU ISOR SUMP Number 0. 1. 0. 0. 0. 0. 0. 0. 0. 0. 0. rms sigma 0.000 0.020 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 rms deviation 0.000 0.017 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.061; Restrained GooF = 1.061 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0496 * P )^2 + 0.61 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.83857 0.00322 0.001 OSF 2 0.03310 0.00575 0.000 EXTI Mean shift/esd = 0.001 Maximum = -0.004 for U23 F2 Max. shift = 0.000 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 2 Maximum vector length = 511 Memory required = 1721 / 169120 wR2 = 0.1394 before cycle 2 for 2048 data and 133 / 133 parameters Summary of restraints applied in cycle 2 ANTIBUMP DFIX DANG SAME/SADI CHIV/Z CHIV/NZ FLAT DELU SIMU ISOR SUMP Number 0. 1. 0. 0. 0. 0. 0. 0. 0. 0. 0. rms sigma 0.000 0.020 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 rms deviation 0.000 0.017 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.061; Restrained GooF = 1.061 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0496 * P )^2 + 0.61 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.83857 0.00322 0.000 OSF 2 0.03310 0.00575 0.000 EXTI Mean shift/esd = 0.001 Maximum = -0.001 for U23 F2 Max. shift = 0.000 A for H8C Max. dU = 0.000 for C9 Least-squares cycle 3 Maximum vector length = 511 Memory required = 1721 / 169120 wR2 = 0.1394 before cycle 3 for 2048 data and 133 / 133 parameters Summary of restraints applied in cycle 3 ANTIBUMP DFIX DANG SAME/SADI CHIV/Z CHIV/NZ FLAT DELU SIMU ISOR SUMP Number 0. 1. 0. 0. 0. 0. 0. 0. 0. 0. 0. rms sigma 0.000 0.020 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 rms deviation 0.000 0.017 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.061; Restrained GooF = 1.061 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0496 * P )^2 + 0.61 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.83857 0.00322 0.000 OSF 2 0.03310 0.00575 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for y C5 Max. shift = 0.000 A for H8A Max. dU = 0.000 for H1N Least-squares cycle 4 Maximum vector length = 511 Memory required = 1721 / 169120 wR2 = 0.1394 before cycle 4 for 2048 data and 133 / 133 parameters Summary of restraints applied in cycle 4 ANTIBUMP DFIX DANG SAME/SADI CHIV/Z CHIV/NZ FLAT DELU SIMU ISOR SUMP Number 0. 1. 0. 0. 0. 0. 0. 0. 0. 0. 0. rms sigma 0.000 0.020 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 rms deviation 0.000 0.017 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.061; Restrained GooF = 1.061 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0496 * P )^2 + 0.61 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.83857 0.00322 0.000 OSF 2 0.03310 0.00575 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for y F1 Max. shift = 0.000 A for C3 Max. dU = 0.000 for H1N Least-squares cycle 5 Maximum vector length = 511 Memory required = 1721 / 169120 wR2 = 0.1394 before cycle 5 for 2048 data and 133 / 133 parameters Summary of restraints applied in cycle 5 ANTIBUMP DFIX DANG SAME/SADI CHIV/Z CHIV/NZ FLAT DELU SIMU ISOR SUMP Number 0. 1. 0. 0. 0. 0. 0. 0. 0. 0. 0. rms sigma 0.000 0.020 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 rms deviation 0.000 0.017 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.061; Restrained GooF = 1.061 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0496 * P )^2 + 0.61 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.83857 0.00322 0.000 OSF 2 0.03310 0.00575 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for OSF Max. shift = 0.000 A for H8B Max. dU = 0.000 for O1 Least-squares cycle 6 Maximum vector length = 511 Memory required = 1721 / 169120 wR2 = 0.1394 before cycle 6 for 2048 data and 133 / 133 parameters Summary of restraints applied in cycle 6 ANTIBUMP DFIX DANG SAME/SADI CHIV/Z CHIV/NZ FLAT DELU SIMU ISOR SUMP Number 0. 1. 0. 0. 0. 0. 0. 0. 0. 0. 0. rms sigma 0.000 0.020 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 rms deviation 0.000 0.017 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.061; Restrained GooF = 1.061 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0496 * P )^2 + 0.61 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.83857 0.00322 0.000 OSF 2 0.03310 0.00575 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for OSF Max. shift = 0.000 A for H1N Max. dU = 0.000 for C1 Largest correlation matrix elements 0.550 EXTI / OSF Idealized hydrogen atom generation before cycle 7 Name x y z AFIX d(X-H) shift Bonded to Conformation determined by H3 0.5288 0.6353 -0.0919 43 0.950 0.000 C3 C4 C2 H4 0.7801 0.7363 -0.1933 43 0.950 0.000 C4 C5 C3 H5 0.9062 0.8972 -0.1466 43 0.950 0.000 C5 C4 C6 H6 0.7656 0.9604 -0.0009 43 0.950 0.000 C6 C5 C1 H8A 0.5988 0.9377 0.3371 137 0.980 0.000 C8 C7 H8A H8B 0.3271 0.9653 0.2715 137 0.980 0.000 C8 C7 H8A H8C 0.5859 1.0409 0.2797 137 0.980 0.000 C8 C7 H8A 2008lsh166 in P2(1)/n ATOM x y z sof U11 U22 U33 U23 U13 U12 Ueq C1 0.56150 0.83580 0.04140 1.00000 0.01774 0.02699 0.02676 0.00084 0.00149 0.00246 0.02381 0.00385 0.00044 0.00017 0.00016 0.00000 0.00105 0.00121 0.00118 0.00092 0.00084 0.00087 0.00050 C2 0.49290 0.73831 0.01408 1.00000 0.01979 0.02758 0.02952 0.00093 0.00139 -0.00091 0.02562 0.00389 0.00044 0.00017 0.00016 0.00000 0.00110 0.00123 0.00127 0.00096 0.00087 0.00092 0.00052 C3 0.57575 0.70155 -0.07329 1.00000 0.03650 0.03149 0.03117 -0.00430 0.00337 -0.00117 0.03300 0.00440 0.00053 0.00019 0.00018 0.00000 0.00138 0.00135 0.00137 0.00106 0.00102 0.00108 0.00059 H3 0.52877 0.63533 -0.09191 1.00000 0.03960 0.00000 0.00000 C4 0.72656 0.76130 -0.13318 1.00000 0.04386 0.03741 0.02783 -0.00125 0.00971 0.00175 0.03613 0.00470 0.00056 0.00020 0.00018 0.00000 0.00152 0.00148 0.00132 0.00109 0.00105 0.00118 0.00062 H4 0.78012 0.73631 -0.19327 1.00000 0.04335 0.00000 0.00000 C5 0.79929 0.85693 -0.10593 1.00000 0.03603 0.03433 0.03241 0.00594 0.01016 0.00011 0.03400 0.00462 0.00053 0.00019 0.00018 0.00000 0.00136 0.00141 0.00135 0.00110 0.00104 0.00111 0.00059 H5 0.90624 0.89721 -0.14660 1.00000 0.04080 0.00000 0.00000 C6 0.71634 0.89432 -0.01918 1.00000 0.02397 0.02773 0.03548 0.00201 0.00424 -0.00038 0.02897 0.00423 0.00047 0.00018 0.00017 0.00000 0.00115 0.00126 0.00136 0.00101 0.00093 0.00095 0.00055 H6 0.76561 0.96045 -0.00092 1.00000 0.03477 0.00000 0.00000 C7 0.65785 0.92092 0.19409 1.00000 0.01813 0.02702 0.03251 0.00114 0.00153 0.00092 0.02587 0.00398 0.00044 0.00017 0.00017 0.00000 0.00110 0.00122 0.00125 0.00098 0.00086 0.00091 0.00052 C8 0.53154 0.97045 0.27781 1.00000 0.02255 0.03709 0.03489 -0.00738 0.00128 -0.00106 0.03151 0.00410 0.00047 0.00019 0.00017 0.00000 0.00117 0.00140 0.00135 0.00109 0.00094 0.00101 0.00057 H8A 0.59883 0.93767 0.33710 1.00000 0.04726 0.00000 0.00000 H8B 0.32715 0.96526 0.27149 1.00000 0.04726 0.00000 0.00000 H8C 0.58590 1.04088 0.27969 1.00000 0.04726 0.00000 0.00000 C9 0.34291 0.67103 0.08005 1.00000 0.02761 0.02790 0.03406 -0.00145 0.00408 0.00068 0.02978 0.00423 0.00049 0.00018 0.00018 0.00000 0.00126 0.00126 0.00135 0.00102 0.00098 0.00099 0.00056 N1 0.47645 0.87651 0.12990 1.00000 0.01555 0.02897 0.02871 -0.00361 0.00377 -0.00038 0.02433 0.00322 0.00037 0.00015 0.00013 0.00000 0.00094 0.00105 0.00104 0.00080 0.00073 0.00076 0.00045 O1 0.91246 0.92125 0.18450 1.00000 0.01663 0.04342 0.04227 -0.00830 0.00272 0.00011 0.03406 0.00285 0.00032 0.00013 0.00012 0.00000 0.00082 0.00109 0.00103 0.00080 0.00066 0.00071 0.00046 F1 0.49558 0.65267 0.16181 1.00000 0.03344 0.04893 0.03814 0.01541 0.00499 0.00677 0.04007 0.00278 0.00030 0.00012 0.00011 0.00000 0.00081 0.00097 0.00085 0.00069 0.00061 0.00067 0.00042 F2 0.28227 0.58183 0.04148 1.00000 0.07056 0.03152 0.05230 -0.00880 0.02385 -0.01931 0.05084 0.00285 0.00037 0.00012 0.00012 0.00000 0.00116 0.00086 0.00102 0.00072 0.00082 0.00078 0.00049 F3 0.10040 0.70897 0.10819 1.00000 0.02159 0.03845 0.04758 0.00436 0.00680 -0.00063 0.03572 0.00252 0.00027 0.00011 0.00011 0.00000 0.00071 0.00085 0.00090 0.00067 0.00059 0.00060 0.00040 H1N 0.30143 0.87908 0.14220 1.00000 0.02961 0.04288 0.00368 0.00198 0.00176 0.00000 0.00671 Final Structure Factor Calculation for 2008lsh166 in P2(1)/n Total number of l.s. parameters = 133 Maximum vector length = 511 Memory required = 1588 / 24017 wR2 = 0.1394 before cycle 7 for 2048 data and 0 / 133 parameters Summary of restraints applied in cycle 7 ANTIBUMP DFIX DANG SAME/SADI CHIV/Z CHIV/NZ FLAT DELU SIMU ISOR SUMP Number 0. 1. 0. 0. 0. 0. 0. 0. 0. 0. 0. rms sigma 0.000 0.020 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 rms deviation 0.000 0.017 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.061; Restrained GooF = 1.061 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0496 * P )^2 + 0.61 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 R1 = 0.0663 for 1485 Fo > 4sig(Fo) and 0.1021 for all 2048 data wR2 = 0.1394, GooF = S = 1.061, Restrained GooF = 1.061 for all data Occupancy sum of asymmetric unit = 14.00 for non-hydrogen and 8.00 for hydrogen atoms Principal mean square atomic displacements U 0.0282 0.0262 0.0171 C1 0.0299 0.0273 0.0196 C2 0.0381 0.0339 0.0270 C3 0.0471 0.0375 0.0238 C4 0.0443 0.0348 0.0230 C5 0.0365 0.0275 0.0230 C6 0.0327 0.0269 0.0180 C7 0.0435 0.0286 0.0225 C8 0.0351 0.0284 0.0258 C9 0.0327 0.0255 0.0148 N1 0.0512 0.0346 0.0165 O1 0.0615 0.0316 0.0271 F1 0.0908 0.0382 0.0236 F2 0.0499 0.0371 0.0202 F3 Analysis of variance for reflections employed in refinement K = Mean[Fo^2] / Mean[Fc^2] for group Fc/Fc(max) 0.000 0.008 0.017 0.025 0.034 0.045 0.058 0.078 0.105 0.155 1.000 Number in group 210. 225. 199. 203. 195. 200. 206. 201. 203. 206. GooF 1.169 1.156 1.017 1.106 1.103 1.046 1.036 0.932 0.912 1.085 K 36.535 5.800 1.432 1.956 1.156 0.986 0.983 0.994 1.010 1.022 Resolution(A) 0.77 0.80 0.83 0.87 0.91 0.97 1.05 1.15 1.32 1.64 inf Number in group 205. 213. 197. 208. 210. 199. 202. 207. 203. 204. GooF 1.067 0.940 1.054 1.086 1.079 1.073 1.127 1.027 0.958 1.179 K 1.197 1.186 1.049 1.034 1.342 1.025 1.037 1.045 1.041 1.012 R1 0.334 0.258 0.212 0.171 0.179 0.081 0.058 0.056 0.052 0.038 Recommended weighting scheme: WGHT 0.0398 0.5994 Note that in most cases convergence will be faster if fixed weights (e.g. the default WGHT 0.1) are retained until the refinement is virtually complete, and only then should the above recommended values be used. Most Disagreeable Reflections (* if suppressed or used for Rfree) h k l Fo^2 Fc^2 Delta(F^2)/esd Fc/Fc(max) Resolution(A) 1 12 0 67.62 26.04 4.57 0.042 1.09 0 1 2 2486.73 4080.28 4.11 0.529 6.19 -1 3 6 34.52 16.77 3.75 0.034 1.92 -1 14 1 49.62 13.41 3.45 0.030 0.94 2 14 0 19.19 0.04 3.38 0.002 0.89 0 4 0 2264.92 2869.52 3.18 0.443 3.35 3 9 1 16.84 4.79 3.15 0.018 1.08 1 13 1 47.55 21.55 2.87 0.038 1.01 -5 3 6 59.11 85.70 2.83 0.077 0.88 0 3 6 304.18 372.26 2.78 0.160 2.06 -3 10 7 1375.40 15.66 2.74 0.033 0.92 -2 1 15 9.31 23.22 2.73 0.040 0.88 -4 1 4 8.50 1.69 2.70 0.011 1.14 1 7 0 9.64 1.23 2.62 0.009 1.78 -2 7 11 37.90 21.02 2.62 0.038 0.98 5 6 8 62.44 112.71 2.62 0.088 0.77 -2 7 14 16.26 0.00 2.60 0.000 0.84 -4 6 1 190.71 144.03 2.59 0.099 1.05 -1 15 1 20.75 7.49 2.55 0.023 0.88 1 9 13 20.48 1.07 2.54 0.009 0.85 1 3 0 502.82 611.04 2.54 0.205 3.26 0 11 10 110.88 79.22 2.53 0.074 0.92 -1 10 12 16.13 0.96 2.53 0.008 0.87 2 9 3 15.65 6.25 2.52 0.021 1.21 -2 8 9 32.53 17.96 2.52 0.035 1.04 4 7 0 585.53 482.66 2.52 0.182 1.01 -4 4 1 8.37 0.02 2.51 0.001 1.13 1 12 4 51.69 72.50 2.50 0.070 1.04 0 12 3 13.19 25.06 2.49 0.041 1.09 4 13 1 33.03 8.61 2.48 0.024 0.78 -3 9 1 697.32 581.66 2.45 0.200 1.09 1 16 3 29.40 11.60 2.45 0.028 0.81 4 6 0 12.70 0.01 2.45 0.001 1.05 2 4 13 15.79 3.68 2.45 0.016 0.93 3 6 1 432.40 362.92 2.41 0.158 1.29 4 8 0 568.72 453.63 2.40 0.176 0.97 -3 8 1 183.88 140.61 2.40 0.098 1.15 1 0 3 17658.09 14592.69 2.38 1.000 3.26 3 13 0 23.28 45.93 2.37 0.056 0.87 1 12 2 62.53 84.55 2.36 0.076 1.07 -4 7 7 59.63 82.94 2.36 0.075 0.92 1 15 5 14.69 1.98 2.34 0.012 0.84 1 14 2 30.74 48.34 2.34 0.058 0.93 -5 7 8 53.14 96.82 2.34 0.081 0.78 4 10 8 30.49 0.11 2.30 0.003 0.78 -4 3 12 9.56 24.03 2.30 0.041 0.84 1 11 0 28.19 13.77 2.29 0.031 1.18 0 3 1 142.00 174.57 2.28 0.109 4.26 0 16 2 17.09 0.00 2.28 0.001 0.83 3 5 12 12.18 27.02 2.27 0.043 0.87 Bond lengths and angles C1 - Distance Angles C6 1.3918 (0.0033) C2 1.3976 (0.0032) 119.12 (0.21) N1 1.4278 (0.0029) 119.39 (0.21) 121.49 (0.20) C1 - C6 C2 C2 - Distance Angles C3 1.3910 (0.0034) C1 1.3976 (0.0032) 119.95 (0.22) C9 1.4960 (0.0033) 119.36 (0.22) 120.63 (0.21) C2 - C3 C1 C3 - Distance Angles C4 1.3846 (0.0036) C2 1.3910 (0.0034) 120.12 (0.24) H3 0.9500 119.94 119.94 C3 - C4 C2 C4 - Distance Angles C5 1.3786 (0.0036) C3 1.3846 (0.0036) 120.24 (0.24) H4 0.9500 119.88 119.88 C4 - C5 C3 C5 - Distance Angles C4 1.3786 (0.0036) C6 1.3865 (0.0034) 120.00 (0.23) H5 0.9500 120.00 120.00 C5 - C4 C6 C6 - Distance Angles C5 1.3865 (0.0034) C1 1.3918 (0.0033) 120.56 (0.23) H6 0.9500 119.72 119.72 C6 - C5 C1 C7 - Distance Angles O1 1.2308 (0.0027) N1 1.3580 (0.0029) 122.39 (0.22) C8 1.4962 (0.0033) 121.27 (0.21) 116.34 (0.19) C7 - O1 N1 C8 - Distance Angles C7 1.4962 (0.0033) H8A 0.9800 109.47 H8B 0.9800 109.47 109.47 H8C 0.9800 109.47 109.47 109.47 C8 - C7 H8A H8B C9 - Distance Angles F2 1.3391 (0.0028) F3 1.3413 (0.0027) 106.42 (0.19) F1 1.3515 (0.0028) 106.07 (0.20) 105.25 (0.19) C2 1.4960 (0.0033) 113.10 (0.20) 113.33 (0.20) 112.06 (0.19) C9 - F2 F3 F1 N1 - Distance Angles C7 1.3580 (0.0029) C1 1.4278 (0.0029) 122.84 (0.19) H1N 0.8626 (0.0167) 116.60 (1.73) 120.27 (1.72) N1 - C7 C1 O1 - Distance Angles C7 1.2308 (0.0027) O1 - F1 - Distance Angles C9 1.3515 (0.0028) F1 - F2 - Distance Angles C9 1.3391 (0.0028) F2 - F3 - Distance Angles C9 1.3413 (0.0027) F3 - Specified hydrogen bonds (with esds except fixed and riding H) D-H H...A D...A <(DHA) 0.863(17) 2.056(18) 2.898(2) 165(3) N1-H1N...O1_$1 0.863(17) 2.51(3) 2.886(2) 107(2) N1-H1N...F3 Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A)