+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + SHELXL-97 - CRYSTAL STRUCTURE REFINEMENT - WinGX VERSION + + Copyright(C) George M. Sheldrick 1993-7 Release 97-2 + + 2008lsh058 started at 18:39:13 on 22-Jul-2008 + +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ TITL 2008lsh058 in P2(1)/n CELL 0.71073 4.6154 5.3698 31.2699 90.000 91.978 90.000 ZERR 4.00 0.0002 0.0002 0.0013 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O UNIT 32 40 8 4 V = 774.52 F(000) = 320.0 Mu = 0.09 mm-1 Cell Wt = 600.72 Rho = 1.288 MERG 2 OMIT -3.00 55.00 OMIT 0 1 5 OMIT 0 4 16 FMAP 2 PLAN 5 ACTA EQIV $1 x+1, y, z EQIV $2 -x+3/2, y+1/2, -z+1/2 HTAB N1 O1_$1 HTAB N2 O1_$1 HTAB N2 O1_$2 HTAB SIZE 0.6 0.08 0.06 BOND $H L.S. 6 TEMP -153.00 WGHT 0.0844 0.4576 FVAR 1.41586 C1 1 0.933856 0.695928 0.140889 11.00000 0.01580 0.02236 = 0.02034 -0.00272 -0.00142 0.00194 C2 1 0.733302 0.512971 0.150098 11.00000 0.03329 0.02602 = 0.01998 0.00115 -0.00001 -0.00475 AFIX 43 H2 2 0.674259 0.490964 0.178657 11.00000 -1.20000 AFIX 0 C3 1 0.618616 0.361962 0.117726 11.00000 0.04456 0.02520 = 0.02713 -0.00128 -0.00075 -0.01221 AFIX 43 H3 2 0.478857 0.239374 0.124418 11.00000 -1.20000 AFIX 0 C4 1 0.703830 0.386158 0.075683 11.00000 0.03232 0.02132 = 0.02278 -0.00133 -0.00449 0.00156 C5 1 0.904721 0.569945 0.067146 11.00000 0.03583 0.03896 = 0.02130 -0.00552 0.00572 -0.00574 AFIX 43 H5 2 0.965596 0.590710 0.038652 11.00000 -1.20000 AFIX 0 C6 1 1.019452 0.724459 0.099020 11.00000 0.03079 0.04038 = 0.02557 -0.00520 0.00727 -0.01548 AFIX 43 H6 2 1.156146 0.849391 0.092224 11.00000 -1.20000 AFIX 0 C7 1 0.915954 0.977805 0.202857 11.00000 0.01415 0.02038 = 0.01709 0.00322 0.00112 -0.00074 C8 1 0.580695 0.219289 0.040691 11.00000 0.05351 0.03131 = 0.02920 -0.00813 -0.00628 -0.00718 AFIX 137 H8A 2 0.643632 0.278927 0.012884 11.00000 -1.50000 H8B 2 0.368495 0.221994 0.041087 11.00000 -1.50000 H8C 2 0.650044 0.048651 0.045391 11.00000 -1.50000 AFIX 0 N1 3 1.064706 0.848462 0.173368 11.00000 0.01254 0.03099 = 0.02248 -0.00631 0.00174 -0.00044 N2 3 1.079075 1.116775 0.230273 11.00000 0.01284 0.03043 = 0.02394 -0.00904 0.00106 0.00035 O1 4 0.646966 0.965877 0.205054 11.00000 0.01218 0.02529 = 0.02069 0.00002 0.00159 -0.00045 H1N 2 1.264842 0.879546 0.173638 11.00000 0.02797 H2AN 2 1.272630 1.122985 0.226223 11.00000 0.02511 H2BN 2 0.988330 1.219496 0.249529 11.00000 0.03891 HKLF 4 Covalent radii and connectivity table for 2008lsh058 in P2(1)/n C 0.770 H 0.320 N 0.700 O 0.660 C1 - C2 C6 N1 C2 - C1 C3 C3 - C2 C4 C4 - C5 C3 C8 C5 - C4 C6 C6 - C5 C1 C7 - O1 N2 N1 C8 - C4 N1 - C7 C1 N2 - C7 O1 - C7 Operators for generating equivalent atoms: $1 x+1, y, z $2 -x+3/2, y+1/2, -z+1/2 6482 Reflections read, of which 508 rejected -5 =< h =< 4, -6 =< k =< 6, -40 =< l =< 40, Max. 2-theta = 54.98 0 Systematic absence violations 0 Inconsistent equivalents 1722 Unique reflections, of which 0 suppressed R(int) = 0.0419 R(sigma) = 0.0460 Friedel opposites merged Maximum memory for data reduction = 1339 / 16873 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 = 1638 / 145148 wR2 = 0.1635 before cycle 1 for 1722 data and 113 / 113 parameters GooF = S = 1.063; Restrained GooF = 1.063 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0844 * P )^2 + 0.46 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.41671 0.00613 0.139 OSF Mean shift/esd = 0.191 Maximum = 0.644 for x C7 Max. shift = 0.006 A for H1N Max. dU = 0.001 for H2BN Least-squares cycle 2 Maximum vector length = 511 Memory required = 1638 / 145148 wR2 = 0.1632 before cycle 2 for 1722 data and 113 / 113 parameters GooF = S = 1.064; Restrained GooF = 1.064 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0844 * P )^2 + 0.46 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.41572 0.00611 -0.163 OSF Mean shift/esd = 0.067 Maximum = 0.233 for x C7 Max. shift = 0.003 A for H2AN Max. dU = 0.001 for H2BN Least-squares cycle 3 Maximum vector length = 511 Memory required = 1638 / 145148 wR2 = 0.1632 before cycle 3 for 1722 data and 113 / 113 parameters GooF = S = 1.064; Restrained GooF = 1.064 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0844 * P )^2 + 0.46 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.41572 0.00611 0.000 OSF Mean shift/esd = 0.005 Maximum = 0.019 for y H2AN Max. shift = 0.000 A for H2AN Max. dU = 0.000 for H2BN Least-squares cycle 4 Maximum vector length = 511 Memory required = 1638 / 145148 wR2 = 0.1632 before cycle 4 for 1722 data and 113 / 113 parameters GooF = S = 1.064; Restrained GooF = 1.064 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0844 * P )^2 + 0.46 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.41575 0.00611 0.006 OSF Mean shift/esd = 0.001 Maximum = 0.008 for U33 C6 Max. shift = 0.000 A for H1N Max. dU = 0.000 for H2BN Least-squares cycle 5 Maximum vector length = 511 Memory required = 1638 / 145148 wR2 = 0.1632 before cycle 5 for 1722 data and 113 / 113 parameters GooF = S = 1.064; Restrained GooF = 1.064 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0844 * P )^2 + 0.46 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.41575 0.00611 0.000 OSF Mean shift/esd = 0.000 Maximum = -0.001 for y H1N Max. shift = 0.000 A for H1N Max. dU = 0.000 for H2BN Least-squares cycle 6 Maximum vector length = 511 Memory required = 1638 / 145148 wR2 = 0.1632 before cycle 6 for 1722 data and 113 / 113 parameters GooF = S = 1.064; Restrained GooF = 1.064 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0844 * P )^2 + 0.46 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.41575 0.00611 0.000 OSF Mean shift/esd = 0.000 Maximum = 0.001 for tors H8A Max. shift = 0.000 A for H8A 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 0.6742 0.4911 0.1786 43 0.950 0.000 C2 C1 C3 H3 0.4791 0.2393 0.1244 43 0.950 0.000 C3 C2 C4 H5 0.9654 0.5909 0.0387 43 0.950 0.000 C5 C4 C6 H6 1.1562 0.8491 0.0923 43 0.950 0.000 C6 C5 C1 H8A 0.6440 0.2783 0.0129 137 0.980 0.000 C8 C4 H8A H8B 0.3686 0.2222 0.0411 137 0.980 0.000 C8 C4 H8A H8C 0.6497 0.0484 0.0455 137 0.980 0.000 C8 C4 H8A 2008lsh058 in P2(1)/n ATOM x y z sof U11 U22 U33 U23 U13 U12 Ueq C1 0.93390 0.69574 0.14091 1.00000 0.01583 0.02202 0.02011 -0.00273 -0.00174 0.00214 0.01937 0.00306 0.00037 0.00035 0.00005 0.00000 0.00083 0.00095 0.00087 0.00071 0.00062 0.00067 0.00041 C2 0.73343 0.51303 0.15008 1.00000 0.03340 0.02582 0.01970 0.00116 -0.00007 -0.00473 0.02633 0.00337 0.00044 0.00039 0.00006 0.00000 0.00110 0.00105 0.00088 0.00078 0.00075 0.00081 0.00047 H2 0.67425 0.49112 0.17864 1.00000 0.03159 0.00000 0.00000 C3 0.61880 0.36198 0.11774 1.00000 0.04418 0.02489 0.02724 -0.00118 -0.00115 -0.01221 0.03216 0.00355 0.00050 0.00040 0.00006 0.00000 0.00124 0.00109 0.00102 0.00084 0.00085 0.00092 0.00051 H3 0.47910 0.23934 0.12443 1.00000 0.03859 0.00000 0.00000 C4 0.70411 0.38629 0.07567 1.00000 0.03235 0.02090 0.02269 -0.00152 -0.00442 0.00171 0.02544 0.00332 0.00043 0.00037 0.00006 0.00000 0.00106 0.00100 0.00095 0.00076 0.00076 0.00077 0.00046 C5 0.90461 0.56992 0.06718 1.00000 0.03612 0.03880 0.02058 -0.00504 0.00573 -0.00582 0.03173 0.00371 0.00047 0.00045 0.00006 0.00000 0.00115 0.00125 0.00093 0.00085 0.00080 0.00091 0.00051 H5 0.96536 0.59089 0.03868 1.00000 0.03807 0.00000 0.00000 C6 1.01940 0.72421 0.09905 1.00000 0.03052 0.03984 0.02526 -0.00479 0.00744 -0.01503 0.03172 0.00352 0.00045 0.00044 0.00006 0.00000 0.00108 0.00127 0.00100 0.00090 0.00080 0.00091 0.00052 H6 1.15620 0.84906 0.09225 1.00000 0.03807 0.00000 0.00000 C7 0.91627 0.97771 0.20287 1.00000 0.01405 0.02017 0.01678 0.00347 0.00105 -0.00053 0.01699 0.00300 0.00036 0.00034 0.00005 0.00000 0.00081 0.00092 0.00079 0.00068 0.00061 0.00065 0.00040 C8 0.58077 0.21914 0.04072 1.00000 0.05373 0.03106 0.02895 -0.00790 -0.00644 -0.00686 0.03809 0.00366 0.00055 0.00044 0.00007 0.00000 0.00145 0.00119 0.00107 0.00093 0.00096 0.00104 0.00056 H8A 0.64398 0.27830 0.01290 1.00000 0.05714 0.00000 0.00000 H8B 0.36857 0.22220 0.04110 1.00000 0.05714 0.00000 0.00000 H8C 0.64973 0.04845 0.04550 1.00000 0.05714 0.00000 0.00000 N1 1.06477 0.84854 0.17335 1.00000 0.01221 0.03132 0.02199 -0.00637 0.00169 -0.00076 0.02182 0.00267 0.00032 0.00032 0.00005 0.00000 0.00074 0.00094 0.00078 0.00066 0.00055 0.00063 0.00039 N2 1.07892 1.11676 0.23027 1.00000 0.01279 0.03014 0.02377 -0.00889 0.00120 0.00028 0.02222 0.00273 0.00033 0.00032 0.00005 0.00000 0.00075 0.00092 0.00079 0.00068 0.00057 0.00063 0.00039 O1 0.64690 0.96583 0.20503 1.00000 0.01172 0.02537 0.02062 0.00021 0.00162 -0.00070 0.01921 0.00213 0.00025 0.00025 0.00004 0.00000 0.00059 0.00073 0.00064 0.00051 0.00044 0.00049 0.00034 H1N 1.26321 0.87961 0.17362 1.00000 0.02832 0.04017 0.00504 0.00438 0.00068 0.00000 0.00581 H2AN 1.27178 1.12432 0.22628 1.00000 0.02618 0.03960 0.00504 0.00445 0.00066 0.00000 0.00568 H2BN 0.98964 1.21877 0.24945 1.00000 0.04113 0.04336 0.00522 0.00510 0.00079 0.00000 0.00690 Final Structure Factor Calculation for 2008lsh058 in P2(1)/n Total number of l.s. parameters = 113 Maximum vector length = 511 Memory required = 1525 / 22995 wR2 = 0.1632 before cycle 7 for 1722 data and 0 / 113 parameters GooF = S = 1.064; Restrained GooF = 1.064 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0844 * P )^2 + 0.46 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 R1 = 0.0529 for 1338 Fo > 4sig(Fo) and 0.0721 for all 1722 data wR2 = 0.1632, GooF = S = 1.064, Restrained GooF = 1.064 for all data Occupancy sum of asymmetric unit = 11.00 for non-hydrogen and 10.00 for hydrogen atoms Principal mean square atomic displacements U 0.0251 0.0183 0.0147 C1 0.0358 0.0237 0.0195 C2 0.0503 0.0276 0.0186 C3 0.0353 0.0212 0.0198 C4 0.0452 0.0315 0.0185 C5 0.0528 0.0243 0.0181 C6 0.0223 0.0151 0.0135 C7 0.0571 0.0380 0.0192 C8 0.0346 0.0188 0.0121 N1 0.0364 0.0176 0.0127 N2 0.0254 0.0207 0.0115 O1 Analysis of variance for reflections employed in refinement K = Mean[Fo^2] / Mean[Fc^2] for group Fc/Fc(max) 0.000 0.013 0.026 0.040 0.055 0.074 0.094 0.118 0.158 0.230 1.000 Number in group 174. 180. 165. 172. 170. 175. 172. 169. 172. 173. GooF 0.882 0.970 1.025 1.149 1.199 1.198 1.013 1.056 1.162 0.941 K 1.079 0.982 0.971 0.956 0.965 1.006 1.018 1.020 1.011 0.995 Resolution(A) 0.77 0.80 0.83 0.87 0.91 0.97 1.05 1.15 1.32 1.66 inf Number in group 174. 173. 175. 169. 173. 171. 177. 167. 170. 173. GooF 1.004 0.945 1.017 0.858 1.143 0.864 1.319 0.950 1.064 1.340 K 1.039 1.045 1.022 1.027 0.979 1.045 0.996 0.985 1.026 0.985 R1 0.145 0.150 0.112 0.097 0.094 0.057 0.067 0.045 0.048 0.044 Recommended weighting scheme: WGHT 0.0810 0.4946 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) 0 4 18 55.05 191.78 8.20 0.194 1.06 0 4 14 1.29 28.61 7.10 0.075 1.15 0 1 4 593.42 1515.55 6.51 0.546 4.43 -2 5 25 1.98 27.17 5.77 0.073 0.77 -1 5 14 -0.03 15.26 5.04 0.055 0.95 0 5 16 60.75 119.10 4.83 0.153 0.94 4 3 1 84.26 144.47 4.04 0.169 0.97 1 1 24 11.10 28.20 4.01 0.074 1.21 1 1 13 26.59 12.65 3.95 0.050 1.96 2 4 19 -2.19 13.63 3.89 0.052 0.94 0 4 21 3.36 18.52 3.72 0.060 1.00 0 3 18 85.81 141.46 3.64 0.167 1.25 2 2 22 55.93 104.91 3.40 0.144 1.09 0 1 1 649.87 936.68 3.36 0.429 5.29 -1 0 17 94.14 63.47 3.30 0.112 1.73 1 5 16 0.94 19.22 3.18 0.061 0.92 2 2 2 7.92 0.82 3.02 0.013 1.73 -2 2 6 152.57 110.85 3.01 0.148 1.67 -1 2 4 51.02 33.96 2.96 0.082 2.24 -5 2 4 7.82 20.83 2.94 0.064 0.87 -3 0 33 -2.85 5.30 2.83 0.032 0.82 -5 2 8 11.39 1.52 2.80 0.017 0.86 5 0 11 3.61 10.64 2.76 0.046 0.87 2 2 27 9.54 0.64 2.72 0.011 0.95 -2 1 11 64.03 45.36 2.71 0.094 1.73 1 3 33 13.43 5.32 2.63 0.032 0.82 -2 4 21 30.69 49.01 2.62 0.098 0.92 1 6 17 6.58 18.07 2.62 0.060 0.79 0 4 0 7.46 3.01 2.60 0.024 1.34 -2 2 2 2.67 0.18 2.57 0.006 1.74 -3 3 6 62.20 41.73 2.54 0.091 1.14 2 2 6 4.23 0.90 2.51 0.013 1.65 -3 5 3 26.80 13.61 2.49 0.052 0.88 -2 5 19 10.41 2.41 2.48 0.022 0.84 -1 4 11 -0.28 18.85 2.48 0.061 1.18 1 6 12 1.11 8.40 2.45 0.041 0.83 3 5 8 43.44 65.89 2.45 0.114 0.86 2 1 25 -1.10 10.62 2.44 0.046 1.06 3 1 17 2.70 0.03 2.41 0.002 1.13 -1 3 9 31.98 21.86 2.39 0.066 1.51 0 3 2 3.63 1.17 2.37 0.015 1.78 4 4 18 35.62 19.21 2.37 0.061 0.77 -3 1 3 11.28 5.48 2.35 0.033 1.47 -3 4 19 52.59 35.27 2.30 0.083 0.87 -1 2 17 19.58 29.34 2.27 0.076 1.45 -1 4 13 1.15 5.70 2.24 0.034 1.14 4 4 2 67.18 49.37 2.23 0.099 0.87 -4 3 4 13.75 5.49 2.19 0.033 0.97 3 0 3 125.09 97.67 2.17 0.139 1.51 2 0 4 330.25 267.13 2.17 0.229 2.19 Bond lengths and angles C1 - Distance Angles C2 1.3854 (0.0027) C6 1.3886 (0.0025) 119.13 (0.17) N1 1.4230 (0.0023) 122.06 (0.16) 118.76 (0.17) C1 - C2 C6 C2 - Distance Angles C1 1.3854 (0.0027) C3 1.3871 (0.0027) 120.25 (0.18) H2 0.9500 119.88 119.88 C2 - C1 C3 C3 - Distance Angles C2 1.3871 (0.0027) C4 1.3922 (0.0027) 121.40 (0.19) H3 0.9500 119.30 119.30 C3 - C2 C4 C4 - Distance Angles C5 1.3842 (0.0030) C3 1.3922 (0.0027) 117.44 (0.18) C8 1.5103 (0.0026) 121.49 (0.18) 121.07 (0.19) C4 - C5 C3 C5 - Distance Angles C4 1.3842 (0.0030) C6 1.3870 (0.0029) 121.94 (0.18) H5 0.9500 119.03 119.03 C5 - C4 C6 C6 - Distance Angles C5 1.3870 (0.0029) C1 1.3886 (0.0025) 119.84 (0.18) H6 0.9500 120.08 120.08 C6 - C5 C1 C7 - Distance Angles O1 1.2491 (0.0021) N2 1.3456 (0.0023) 121.90 (0.16) N1 1.3590 (0.0022) 122.47 (0.16) 115.62 (0.15) C7 - O1 N2 C8 - Distance Angles C4 1.5103 (0.0026) H8A 0.9800 109.47 H8B 0.9800 109.47 109.47 H8C 0.9800 109.47 109.47 109.47 C8 - C4 H8A H8B N1 - Distance Angles C7 1.3590 (0.0022) C1 1.4230 (0.0023) 124.54 (0.15) H1N 0.9307 (0.0232) 114.94 (1.39) 120.21 (1.37) N1 - C7 C1 N2 - Distance Angles C7 1.3456 (0.0023) H2AN 0.9040 (0.0230) 117.88 (1.41) H2BN 0.9201 (0.0268) 119.53 (1.53) 121.89 (2.07) N2 - C7 H2AN O1 - Distance Angles C7 1.2491 (0.0021) O1 - Specified hydrogen bonds (with esds except fixed and riding H) D-H H...A D...A <(DHA) 0.93(2) 2.05(2) 2.9005(19) 151.5(19) N1-H1N...O1_$1 0.90(2) 2.06(2) 2.880(2) 150(2) N2-H2AN...O1_$1 0.92(3) 2.06(3) 2.973(2) 171(2) N2-H2BN...O1_$2 Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A)