+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + SHELXL-97 - CRYSTAL STRUCTURE REFINEMENT - WinGX VERSION + + Copyright(C) George M. Sheldrick 1993-7 Release 97-2 + + 2008lsh050 started at 15:24:53 on 21-Jul-2008 + +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ TITL 2008lsh050 in Pna2(1) CELL 0.71073 10.5957 7.6655 9.2544 90.000 90.000 90.000 ZERR 4.00 0.0003 0.0003 0.0002 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, Z SYMM 1/2 - X, 1/2 + Y, 1/2 + Z SFAC C H N O UNIT 32 36 4 8 V = 751.65 F(000) = 320.0 Mu = 0.10 mm-1 Cell Wt = 604.65 Rho = 1.336 MERG 2 OMIT -3.00 55.00 OMIT 0 0 2 OMIT 2 0 2 OMIT 2 0 -1 EQIV $1 -x+1, -y, z-1/2 HTAB N1 O1_$1 FMAP 2 PLAN 5 SIZE 0.40 0.60 0.70 ACTA HTAB 2.00000 BOND $H WGHT 0.03420 0.13610 L.S. 6 TEMP -153.00 FVAR 2.24876 C1 1 0.575099 0.301797 0.109620 11.00000 0.01937 0.02143 = 0.01591 0.00269 -0.00343 0.00115 C2 1 0.544510 0.409711 0.226167 11.00000 0.02215 0.02252 = 0.01628 0.00268 0.00190 0.00196 AFIX 43 H2 2 0.488357 0.369696 0.299007 11.00000 -1.20000 AFIX 0 C3 1 0.596383 0.575312 0.235107 11.00000 0.02547 0.02328 = 0.01775 -0.00073 0.00179 0.00274 AFIX 43 H3 2 0.576346 0.647994 0.315026 11.00000 -1.20000 AFIX 0 C4 1 0.677538 0.636195 0.128167 11.00000 0.01968 0.02058 = 0.02077 0.00435 -0.00292 -0.00022 C5 1 0.705833 0.531250 0.009472 11.00000 0.02030 0.02894 = 0.01724 0.00546 0.00222 0.00014 AFIX 43 H5 2 0.759287 0.573247 -0.065240 11.00000 -1.20000 AFIX 0 C6 1 0.654827 0.364259 0.001776 11.00000 0.02291 0.02523 = 0.01560 -0.00058 -0.00003 0.00323 AFIX 43 H6 2 0.674700 0.291729 -0.078292 11.00000 -1.20000 AFIX 0 C7 1 0.490743 0.023653 0.201835 11.00000 0.02329 0.02195 = 0.02063 -0.00013 -0.00183 -0.00074 AFIX 43 H7 2 0.462835 -0.089545 0.174903 11.00000 -1.20000 AFIX 0 C8 1 0.789985 0.879518 0.031654 11.00000 0.02637 0.03042 = 0.03171 0.01043 -0.00190 -0.00579 AFIX 137 H8A 2 0.868140 0.815459 0.011870 11.00000 -1.50000 H8B 2 0.810183 1.000905 0.055521 11.00000 -1.50000 H8C 2 0.735646 0.876456 -0.054001 11.00000 -1.50000 AFIX 0 N1 3 0.524401 0.131330 0.094803 11.00000 0.02659 0.02195 = 0.01441 -0.00114 -0.00148 -0.00091 O1 4 0.492479 0.057207 0.331720 11.00000 0.03828 0.02608 = 0.01911 0.00199 0.00154 -0.00433 O2 4 0.725779 0.800353 0.150653 11.00000 0.03168 0.02465 = 0.02601 0.00320 -0.00114 -0.00601 H1N 2 0.522994 0.090181 0.006041 11.00000 0.03564 HKLF 4 1.0 0.00 0.00 1.00 1.00 0.00 0.00 0.00 1.00 0.00 Covalent radii and connectivity table for 2008lsh050 in Pna2(1) C 0.770 H 0.320 N 0.700 O 0.660 C1 - C6 C2 N1 C2 - C3 C1 C3 - C2 C4 C4 - O2 C3 C5 C5 - C6 C4 C6 - C5 C1 C7 - O1 N1 C8 - O2 N1 - C7 C1 O1 - C7 O2 - C4 C8 Operators for generating equivalent atoms: $1 -x+1, -y, z-1/2 Floating origin restraints generated h k l Fo^2 Sigma Why rejected 1 0 -1 7.50 1.85 observed but should be systematically absent 7319 Reflections read, of which 518 rejected -13 =< h =< 13, -9 =< k =< 9, -11 =< l =< 11, Max. 2-theta = 54.93 1 Systematic absence violations 0 Inconsistent equivalents 1663 Unique reflections, of which 0 suppressed R(int) = 0.0280 R(sigma) = 0.0261 Friedel opposites not merged Maximum memory for data reduction = 1252 / 16430 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 = 1534 / 136080 wR2 = 0.0713 before cycle 1 for 1663 data and 105 / 105 parameters GooF = S = 1.061; Restrained GooF = 1.060 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0342 * P )^2 + 0.14 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.24051 0.00442 -1.866 OSF Mean shift/esd = 0.394 Maximum = -1.866 for OSF Max. shift = 0.018 A for H1N Max. dU =-0.002 for H1N Least-squares cycle 2 Maximum vector length = 511 Memory required = 1534 / 136080 wR2 = 0.0706 before cycle 2 for 1663 data and 105 / 105 parameters GooF = S = 1.053; Restrained GooF = 1.053 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0342 * P )^2 + 0.14 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.23724 0.00437 -0.749 OSF Mean shift/esd = 0.129 Maximum = -0.749 for OSF Max. shift = 0.006 A for H1N Max. dU =-0.001 for H1N Least-squares cycle 3 Maximum vector length = 511 Memory required = 1534 / 136080 wR2 = 0.0705 before cycle 3 for 1663 data and 105 / 105 parameters GooF = S = 1.053; Restrained GooF = 1.053 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0342 * P )^2 + 0.14 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.23722 0.00436 -0.004 OSF Mean shift/esd = 0.004 Maximum = -0.026 for U11 H1N Max. shift = 0.000 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 4 Maximum vector length = 511 Memory required = 1534 / 136080 wR2 = 0.0705 before cycle 4 for 1663 data and 105 / 105 parameters GooF = S = 1.053; Restrained GooF = 1.053 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0342 * P )^2 + 0.14 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.23721 0.00436 -0.002 OSF Mean shift/esd = 0.002 Maximum = -0.007 for z C6 Max. shift = 0.000 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 5 Maximum vector length = 511 Memory required = 1534 / 136080 wR2 = 0.0705 before cycle 5 for 1663 data and 105 / 105 parameters GooF = S = 1.053; Restrained GooF = 1.053 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0342 * P )^2 + 0.14 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.23722 0.00436 0.001 OSF Mean shift/esd = 0.000 Maximum = 0.001 for OSF Max. shift = 0.000 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 6 Maximum vector length = 511 Memory required = 1534 / 136080 wR2 = 0.0705 before cycle 6 for 1663 data and 105 / 105 parameters GooF = S = 1.053; Restrained GooF = 1.053 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0342 * P )^2 + 0.14 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.23722 0.00436 0.000 OSF Mean shift/esd = 0.000 Maximum = 0.000 for OSF Max. shift = 0.000 A for H1N Max. dU = 0.000 for H1N No correlation matrix elements larger than 0.500 Idealized hydrogen atom generation before cycle 7 Name x y z AFIX d(X-H) shift Bonded to Conformation determined by H2 0.4884 0.3697 0.2989 43 0.950 0.000 C2 C3 C1 H3 0.5764 0.6478 0.3148 43 0.950 0.000 C3 C2 C4 H5 0.7594 0.5734 -0.0650 43 0.950 0.000 C5 C6 C4 H6 0.6747 0.2918 -0.0782 43 0.950 0.000 C6 C5 C1 H7 0.4627 -0.0894 0.1748 43 0.950 0.000 C7 O1 N1 H8A 0.8677 0.8149 0.0114 137 0.980 0.000 C8 O2 H8A H8B 0.8109 1.0006 0.0560 137 0.980 0.000 C8 O2 H8A H8C 0.7354 0.8776 -0.0537 137 0.980 0.000 C8 O2 H8A 2008lsh050 in Pna2(1) ATOM x y z sof U11 U22 U33 U23 U13 U12 Ueq C1 0.57506 0.30188 0.10969 1.00000 0.01894 0.02077 0.01529 0.00259 -0.00351 0.00112 0.01834 0.00204 0.00011 0.00016 0.00012 0.00000 0.00057 0.00064 0.00057 0.00049 0.00046 0.00045 0.00026 C2 0.54454 0.40964 0.22607 1.00000 0.02185 0.02222 0.01590 0.00264 0.00213 0.00204 0.01999 0.00217 0.00011 0.00017 0.00013 0.00000 0.00055 0.00060 0.00057 0.00050 0.00046 0.00049 0.00026 H2 0.48839 0.36967 0.29894 1.00000 0.02399 0.00000 0.00000 C3 0.59646 0.57516 0.23493 1.00000 0.02499 0.02245 0.01727 -0.00103 0.00149 0.00278 0.02157 0.00224 0.00012 0.00017 0.00014 0.00000 0.00057 0.00062 0.00059 0.00049 0.00047 0.00049 0.00026 H3 0.57643 0.64784 0.31485 1.00000 0.02588 0.00000 0.00000 C4 0.67754 0.63608 0.12817 1.00000 0.01921 0.01988 0.02063 0.00414 -0.00343 -0.00010 0.01991 0.00218 0.00012 0.00016 0.00013 0.00000 0.00054 0.00063 0.00066 0.00051 0.00046 0.00045 0.00027 C5 0.70587 0.53137 0.00964 1.00000 0.01980 0.02875 0.01696 0.00576 0.00232 0.00028 0.02184 0.00228 0.00011 0.00017 0.00014 0.00000 0.00053 0.00066 0.00060 0.00051 0.00050 0.00050 0.00027 H5 0.75937 0.57339 -0.06502 1.00000 0.02621 0.00000 0.00000 C6 0.65483 0.36433 0.00188 1.00000 0.02248 0.02483 0.01520 -0.00014 -0.00009 0.00311 0.02084 0.00218 0.00011 0.00017 0.00013 0.00000 0.00058 0.00070 0.00059 0.00050 0.00049 0.00047 0.00027 H6 0.67471 0.29182 -0.07819 1.00000 0.02500 0.00000 0.00000 C7 0.49068 0.02372 0.20178 1.00000 0.02279 0.02132 0.02082 0.00002 -0.00190 -0.00077 0.02164 0.00228 0.00011 0.00017 0.00014 0.00000 0.00061 0.00061 0.00068 0.00053 0.00048 0.00047 0.00027 H7 0.46265 -0.08941 0.17484 1.00000 0.02597 0.00000 0.00000 C8 0.78997 0.87960 0.03173 1.00000 0.02599 0.03009 0.03121 0.01025 -0.00181 -0.00607 0.02910 0.00251 0.00013 0.00019 0.00016 0.00000 0.00062 0.00070 0.00072 0.00061 0.00056 0.00057 0.00031 H8A 0.86772 0.81487 0.01137 1.00000 0.04365 0.00000 0.00000 H8B 0.81089 1.00063 0.05603 1.00000 0.04365 0.00000 0.00000 H8C 0.73536 0.87762 -0.05371 1.00000 0.04365 0.00000 0.00000 N1 0.52435 0.13132 0.09478 1.00000 0.02644 0.02150 0.01397 -0.00136 -0.00156 -0.00101 0.02063 0.00194 0.00010 0.00015 0.00012 0.00000 0.00051 0.00055 0.00053 0.00044 0.00043 0.00042 0.00023 O1 0.49252 0.05719 0.33169 1.00000 0.03780 0.02580 0.01865 0.00179 0.00156 -0.00438 0.02742 0.00177 0.00009 0.00012 0.00012 0.00000 0.00061 0.00049 0.00047 0.00042 0.00039 0.00044 0.00024 O2 0.72572 0.80037 0.15064 1.00000 0.03141 0.02408 0.02565 0.00320 -0.00133 -0.00609 0.02704 0.00162 0.00009 0.00013 0.00010 0.00000 0.00046 0.00048 0.00051 0.00038 0.00042 0.00039 0.00023 H1N 0.52382 0.08874 0.00818 1.00000 0.03263 0.03255 0.00158 0.00222 0.00216 0.00000 0.00449 Final Structure Factor Calculation for 2008lsh050 in Pna2(1) Total number of l.s. parameters = 105 Maximum vector length = 511 Memory required = 1431 / 25046 wR2 = 0.0705 before cycle 7 for 1663 data and 2 / 105 parameters GooF = S = 1.053; Restrained GooF = 1.053 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0342 * P )^2 + 0.14 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 R1 = 0.0287 for 1577 Fo > 4sig(Fo) and 0.0313 for all 1663 data wR2 = 0.0705, GooF = S = 1.053, Restrained GooF = 1.053 for all data Flack x parameter = 0.5452 with esd 0.9853 Expected values are 0 (within 3 esd's) for correct and +1 for inverted absolute structure. Note that this rough estimate ignores correlation with other parameters; if the above value differs significantly from zero, it is ESSENTIAL to test the inverted structure or refine x as a full-matrix parameter using TWIN and BASF Absolute structure cannot be determined reliably Occupancy sum of asymmetric unit = 11.00 for non-hydrogen and 9.00 for hydrogen atoms Principal mean square atomic displacements U 0.0219 0.0209 0.0122 C1 0.0253 0.0200 0.0147 C2 0.0268 0.0213 0.0165 C3 0.0256 0.0194 0.0148 C4 0.0312 0.0204 0.0139 C5 0.0270 0.0203 0.0152 C6 0.0241 0.0212 0.0196 C7 0.0428 0.0258 0.0187 C8 0.0268 0.0216 0.0135 N1 0.0393 0.0251 0.0179 O1 0.0356 0.0257 0.0198 O2 Analysis of variance for reflections employed in refinement K = Mean[Fo^2] / Mean[Fc^2] for group Fc/Fc(max) 0.000 0.049 0.077 0.097 0.119 0.148 0.181 0.219 0.275 0.369 1.000 Number in group 170. 174. 155. 168. 166. 165. 166. 166. 169. 164. GooF 1.113 1.205 1.093 1.077 1.048 0.965 0.915 0.960 0.881 1.216 K 0.993 0.968 0.969 0.973 0.992 1.001 1.004 1.019 1.013 0.993 Resolution(A) 0.77 0.81 0.84 0.87 0.92 0.98 1.05 1.15 1.31 1.66 inf Number in group 169. 165. 165. 166. 175. 159. 167. 164. 168. 165. GooF 0.985 1.141 0.925 1.003 0.831 0.876 0.942 0.830 1.135 1.628 K 1.007 0.997 1.008 1.001 1.006 1.007 0.998 1.018 1.015 0.984 R1 0.063 0.078 0.050 0.042 0.027 0.024 0.020 0.018 0.023 0.027 Recommended weighting scheme: WGHT 0.0292 0.1377 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) 4 0 -3 16.89 9.25 4.55 0.068 2.01 4 0 3 15.92 9.24 4.30 0.068 2.01 1 3 -3 4.25 1.60 4.09 0.028 1.93 1 3 3 4.54 1.61 3.78 0.028 1.93 2 0 0 595.12 688.07 3.50 0.586 5.30 7 4 9 15.73 28.67 3.48 0.120 0.78 2 4 0 11.03 6.36 3.42 0.056 1.80 4 3 0 12.77 18.61 3.31 0.096 1.84 1 7 8 95.03 72.23 3.30 0.190 0.79 5 3 0 1.88 0.23 3.24 0.011 1.63 3 2 0 165.59 191.68 3.12 0.309 2.60 2 2 0 1389.87 1562.72 3.09 0.883 3.11 4 3 4 21.36 15.81 3.03 0.089 1.44 8 6 5 9.65 3.30 2.97 0.041 0.82 1 4 7 23.96 17.83 2.90 0.094 1.08 1 1 1 525.98 602.77 2.89 0.549 5.16 9 1 -8 63.45 50.78 2.85 0.159 0.82 2 2 5 365.13 324.76 2.81 0.403 1.59 1 2 -4 119.48 103.60 2.80 0.227 1.95 1 7 0 22.61 29.41 2.75 0.121 1.09 10 0 5 1.61 4.62 2.74 0.048 0.92 3 4 0 31.93 39.41 2.74 0.140 1.68 11 5 3 13.72 20.08 2.69 0.100 0.79 2 1 -2 778.59 864.56 2.67 0.657 3.17 6 3 -8 3.10 5.92 2.64 0.054 0.90 8 3 8 167.63 142.86 2.62 0.267 0.82 0 3 -3 14.77 10.82 2.61 0.074 1.97 2 1 0 298.46 333.66 2.60 0.408 4.36 1 1 -1 542.34 602.70 2.56 0.549 5.16 2 7 0 21.83 28.17 2.54 0.119 1.07 10 6 0 -0.30 1.93 2.46 0.031 0.82 5 3 7 42.54 51.13 2.45 0.160 1.03 5 6 0 115.85 132.00 2.42 0.257 1.09 1 4 -7 23.65 17.80 2.41 0.094 1.08 2 1 2 786.77 864.85 2.41 0.657 3.17 4 0 11 16.28 23.54 2.38 0.108 0.80 4 7 -1 18.75 14.05 2.37 0.084 1.01 1 1 5 104.52 92.15 2.36 0.215 1.77 0 4 -10 23.84 30.83 2.35 0.124 0.83 6 3 8 3.05 5.89 2.35 0.054 0.90 2 4 2 29.37 24.06 2.34 0.110 1.68 4 8 1 6.54 9.87 2.34 0.070 0.90 5 5 -7 13.10 17.44 2.33 0.093 0.91 8 0 0 1.66 0.44 2.33 0.015 1.32 0 3 3 14.55 10.78 2.33 0.073 1.97 5 6 2 47.67 56.14 2.33 0.167 1.06 0 7 7 54.09 42.33 2.32 0.145 0.84 4 7 1 18.33 14.05 2.30 0.084 1.01 6 3 5 6.94 9.90 2.29 0.070 1.14 1 4 2 244.81 220.85 2.28 0.332 1.75 Bond lengths and angles C1 - Distance Angles C6 1.3925 (0.0016) C2 1.3953 (0.0017) 119.36 (0.12) N1 1.4202 (0.0017) 118.46 (0.11) 122.16 (0.11) C1 - C6 C2 C2 - Distance Angles C3 1.3853 (0.0018) C1 1.3953 (0.0017) 119.72 (0.11) H2 0.9500 120.14 120.14 C2 - C3 C1 C3 - Distance Angles C2 1.3853 (0.0018) C4 1.3901 (0.0017) 120.74 (0.12) H3 0.9500 119.63 119.63 C3 - C2 C4 C4 - Distance Angles O2 1.3747 (0.0015) C3 1.3901 (0.0017) 115.45 (0.11) C5 1.3920 (0.0019) 124.57 (0.11) 119.97 (0.12) C4 - O2 C3 C5 - Distance Angles C6 1.3918 (0.0018) C4 1.3920 (0.0019) 119.17 (0.12) H5 0.9500 120.42 120.42 C5 - C6 C4 C6 - Distance Angles C5 1.3918 (0.0019) C1 1.3925 (0.0016) 121.01 (0.12) H6 0.9500 119.50 119.50 C6 - C5 C1 C7 - Distance Angles O1 1.2294 (0.0017) N1 1.3372 (0.0017) 126.24 (0.13) H7 0.9500 116.88 116.88 C7 - O1 N1 C8 - Distance Angles O2 1.4294 (0.0016) H8A 0.9800 109.47 H8B 0.9800 109.47 109.47 H8C 0.9800 109.47 109.47 109.47 C8 - O2 H8A H8B N1 - Distance Angles C7 1.3372 (0.0017) C1 1.4202 (0.0017) 126.64 (0.11) H1N 0.8654 (0.0198) 116.83 (1.14) 116.08 (1.14) N1 - C7 C1 O1 - Distance Angles C7 1.2294 (0.0017) O1 - O2 - Distance Angles C4 1.3747 (0.0015) C8 1.4294 (0.0016) 116.72 (0.11) O2 - C4 Specified hydrogen bonds (with esds except fixed and riding H) D-H H...A D...A <(DHA) 0.87(2) 1.99(2) 2.8369(16) 166.9(16) N1-H1N...O1_$1 Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A)