+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + SHELXL-97 - CRYSTAL STRUCTURE REFINEMENT - WinGX VERSION + + Copyright(C) George M. Sheldrick 1993-7 Release 97-2 + + shelxl started at 22:50:35 on 13-Nov-2010 + +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ TITL 2008lsh039 in P2(1)2(1)2(1) CELL 0.71073 4.9076 9.7504 18.6116 90.000 90.000 90.000 ZERR 4.00 0.0005 0.0008 0.0011 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O I UNIT 32 32 4 4 4 V = 890.58 F(000) = 496.0 Mu = 3.54 mm-1 Cell Wt = 1044.22 Rho = 1.947 MERG 2 OMIT -3.00 55.00 OMIT 0 10 0 EQIV $1 -x-1, y+1/2, -z+3/2 HTAB N1 O1_$1 FMAP 2 PLAN 5 SIZE 0.02 0.04 0.40 ACTA HTAB 2.00000 BOND $H WGHT 0.03640 5.66610 L.S. 6 TEMP -153.00 FVAR 0.44611 C1 1 -0.155715 1.218837 0.669625 11.00000 0.02635 0.03286 = 0.02008 0.00110 -0.00170 0.00099 C2 1 -0.099682 1.093451 0.637053 11.00000 0.03958 0.01718 = 0.02961 0.00335 -0.00440 -0.00584 AFIX 43 H2 2 -0.202162 1.014061 0.649109 11.00000 -1.20000 AFIX 0 C3 1 0.109820 1.086272 0.586321 11.00000 0.03248 0.02963 = 0.02190 -0.00193 -0.00214 0.00535 C4 1 0.256627 1.199864 0.565916 11.00000 0.02746 0.04122 = 0.02779 0.00270 -0.00310 -0.00071 AFIX 43 H4 2 0.395731 1.193381 0.530582 11.00000 -1.20000 AFIX 0 C5 1 0.194993 1.326011 0.598855 11.00000 0.04629 0.03705 = 0.03830 0.00054 -0.00437 -0.01497 AFIX 43 H5 2 0.295031 1.405954 0.586383 11.00000 -1.20000 AFIX 0 C6 1 -0.010806 1.333679 0.649296 11.00000 0.03638 0.02466 = 0.03382 -0.00269 -0.00235 -0.00182 AFIX 43 H6 2 -0.053427 1.419749 0.670413 11.00000 -1.20000 AFIX 0 C7 1 -0.497226 1.142291 0.758943 11.00000 0.03463 0.02917 = 0.02508 -0.00218 -0.00209 -0.00040 C8 1 -0.699526 1.194523 0.813228 11.00000 0.04576 0.02399 = 0.03369 -0.00250 0.00468 0.00086 AFIX 137 H8A 2 -0.878513 1.153788 0.803758 11.00000 -1.50000 H8B 2 -0.712407 1.294585 0.809617 11.00000 -1.50000 H8C 2 -0.639365 1.169201 0.861653 11.00000 -1.50000 AFIX 0 N1 3 -0.358559 1.237758 0.721911 11.00000 0.03059 0.03043 = 0.03227 -0.00134 0.00245 0.00171 AFIX 43 H1 2 -0.400371 1.323504 0.731716 11.00000 -1.20000 AFIX 0 O1 4 -0.465268 1.016876 0.750403 11.00000 0.04565 0.02616 = 0.04610 0.00363 0.01201 0.00168 I1 5 0.198006 0.896336 0.538865 11.00000 0.04849 0.03703 = 0.03594 -0.00806 0.00575 0.00620 HKLF 4 Covalent radii and connectivity table for 2008lsh039 in P2(1)2(1)2(1) C 0.770 H 0.320 N 0.700 O 0.660 I 1.330 C1 - C6 C2 N1 C2 - C1 C3 C3 - C4 C2 I1 C4 - C3 C5 C5 - C6 C4 C6 - C1 C5 C7 - O1 N1 C8 C8 - C7 N1 - C7 C1 O1 - C7 I1 - C3 Operators for generating equivalent atoms: $1 -x-1, y+1/2, -z+3/2 4208 Reflections read, of which 24 rejected -6 =< h =< 6, -12 =< k =< 11, -23 =< l =< 24, Max. 2-theta = 54.99 0 Systematic absence violations 0 Inconsistent equivalents 1755 Unique reflections, of which 0 suppressed R(int) = 0.0541 R(sigma) = 0.0642 Friedel opposites not merged Maximum memory for data reduction = 1224 / 18116 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 = 1502 / 132592 wR2 = 0.1264 before cycle 1 for 1755 data and 101 / 101 parameters GooF = S = 1.100; Restrained GooF = 1.100 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0364 * P )^2 + 5.67 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.44618 0.00141 0.047 OSF Mean shift/esd = 0.009 Maximum = 0.047 for OSF Max. shift = 0.001 A for H8B Max. dU = 0.000 for C3 Least-squares cycle 2 Maximum vector length = 511 Memory required = 1502 / 132592 wR2 = 0.1264 before cycle 2 for 1755 data and 101 / 101 parameters GooF = S = 1.100; Restrained GooF = 1.100 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0364 * P )^2 + 5.67 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.44617 0.00141 -0.006 OSF Mean shift/esd = 0.003 Maximum = -0.013 for U23 I1 Max. shift = 0.001 A for H8B Max. dU = 0.000 for C3 Least-squares cycle 3 Maximum vector length = 511 Memory required = 1502 / 132592 wR2 = 0.1264 before cycle 3 for 1755 data and 101 / 101 parameters GooF = S = 1.100; Restrained GooF = 1.100 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0364 * P )^2 + 5.67 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.44617 0.00141 0.000 OSF Mean shift/esd = 0.000 Maximum = -0.002 for tors H8A Max. shift = 0.000 A for H8C Max. dU = 0.000 for C4 Least-squares cycle 4 Maximum vector length = 511 Memory required = 1502 / 132592 wR2 = 0.1264 before cycle 4 for 1755 data and 101 / 101 parameters GooF = S = 1.100; Restrained GooF = 1.100 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0364 * P )^2 + 5.67 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.44617 0.00141 0.000 OSF Mean shift/esd = 0.000 Maximum = -0.001 for tors H8A Max. shift = 0.000 A for H8C Max. dU = 0.000 for C5 Least-squares cycle 5 Maximum vector length = 511 Memory required = 1502 / 132592 wR2 = 0.1264 before cycle 5 for 1755 data and 101 / 101 parameters GooF = S = 1.100; Restrained GooF = 1.100 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0364 * P )^2 + 5.67 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.44617 0.00141 0.000 OSF Mean shift/esd = 0.000 Maximum = 0.000 for z I1 Max. shift = 0.000 A for H8B Max. dU = 0.000 for O1 Least-squares cycle 6 Maximum vector length = 511 Memory required = 1502 / 132592 wR2 = 0.1264 before cycle 6 for 1755 data and 101 / 101 parameters GooF = S = 1.100; Restrained GooF = 1.100 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0364 * P )^2 + 5.67 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.44617 0.00141 0.000 OSF Mean shift/esd = 0.000 Maximum = 0.000 for z I1 Max. shift = 0.000 A for H8C Max. dU = 0.000 for O1 Largest correlation matrix elements 0.565 U22 I1 / OSF 0.561 U33 I1 / OSF 0.552 U11 I1 / OSF Idealized hydrogen atom generation before cycle 7 Name x y z AFIX d(X-H) shift Bonded to Conformation determined by H2 -0.2022 1.0141 0.6491 43 0.950 0.000 C2 C1 C3 H4 0.3958 1.1934 0.5306 43 0.950 0.000 C4 C3 C5 H5 0.2951 1.4060 0.5864 43 0.950 0.000 C5 C6 C4 H6 -0.0534 1.4197 0.6704 43 0.950 0.000 C6 C1 C5 H8A -0.8786 1.1539 0.8037 137 0.980 0.000 C8 C7 H8A H8B -0.7121 1.2946 0.8097 137 0.980 0.000 C8 C7 H8A H8C -0.6395 1.1691 0.8617 137 0.980 0.000 C8 C7 H8A H1 -0.4004 1.3235 0.7317 43 0.880 0.000 N1 C7 C1 2008lsh039 in P2(1)2(1)2(1) ATOM x y z sof U11 U22 U33 U23 U13 U12 Ueq C1 -0.15571 1.21883 0.66963 1.00000 0.02635 0.03284 0.02008 0.00112 -0.00175 0.00091 0.02643 0.01400 0.00176 0.00083 0.00039 0.00000 0.00444 0.00432 0.00310 0.00296 0.00318 0.00354 0.00171 C2 -0.09968 1.09345 0.63705 1.00000 0.03951 0.01722 0.02964 0.00341 -0.00441 -0.00583 0.02879 0.01375 0.00183 0.00085 0.00041 0.00000 0.00435 0.00360 0.00347 0.00318 0.00329 0.00364 0.00164 H2 -0.20219 1.01406 0.64910 1.00000 0.03455 0.00000 0.00000 C3 0.10978 1.08625 0.58633 1.00000 0.03242 0.02963 0.02185 -0.00193 -0.00216 0.00537 0.02797 0.01426 0.00180 0.00087 0.00039 0.00000 0.00420 0.00440 0.00316 0.00315 0.00300 0.00363 0.00172 C4 0.25668 1.19988 0.56591 1.00000 0.02747 0.04128 0.02780 0.00271 -0.00309 -0.00070 0.03219 0.01490 0.00174 0.00093 0.00043 0.00000 0.00500 0.00468 0.00335 0.00339 0.00309 0.00381 0.00190 H4 0.39579 1.19338 0.53058 1.00000 0.03862 0.00000 0.00000 C5 0.19506 1.32601 0.59885 1.00000 0.04624 0.03703 0.03837 0.00053 -0.00430 -0.01496 0.04055 0.01625 0.00243 0.00096 0.00049 0.00000 0.00503 0.00481 0.00431 0.00362 0.00478 0.00496 0.00206 H5 0.29509 1.40596 0.58637 1.00000 0.04866 0.00000 0.00000 C6 -0.01079 1.33367 0.64931 1.00000 0.03635 0.02468 0.03376 -0.00273 -0.00234 -0.00180 0.03159 0.01530 0.00199 0.00090 0.00049 0.00000 0.00495 0.00434 0.00421 0.00335 0.00381 0.00359 0.00191 H6 -0.05341 1.41974 0.67043 1.00000 0.03791 0.00000 0.00000 C7 -0.49725 1.14228 0.75894 1.00000 0.03447 0.02929 0.02511 -0.00222 -0.00206 -0.00038 0.02962 0.01590 0.00222 0.00090 0.00044 0.00000 0.00448 0.00421 0.00382 0.00306 0.00355 0.00330 0.00182 C8 -0.69952 1.19454 0.81323 1.00000 0.04583 0.02385 0.03373 -0.00263 0.00471 0.00085 0.03447 0.01657 0.00225 0.00085 0.00043 0.00000 0.00484 0.00393 0.00390 0.00311 0.00425 0.00442 0.00181 H8A -0.87859 1.15393 0.80372 1.00000 0.05171 0.00000 0.00000 H8B -0.71215 1.29462 0.80968 1.00000 0.05171 0.00000 0.00000 H8C -0.63950 1.16908 0.86165 1.00000 0.05171 0.00000 0.00000 N1 -0.35855 1.23775 0.72191 1.00000 0.03063 0.03045 0.03220 -0.00134 0.00248 0.00172 0.03109 0.01246 0.00152 0.00074 0.00039 0.00000 0.00439 0.00359 0.00341 0.00288 0.00308 0.00303 0.00164 H1 -0.40037 1.32349 0.73171 1.00000 0.03731 0.00000 0.00000 O1 -0.46525 1.01688 0.75041 1.00000 0.04566 0.02613 0.04607 0.00367 0.01205 0.00168 0.03928 0.01280 0.00155 0.00063 0.00037 0.00000 0.00431 0.00328 0.00359 0.00276 0.00315 0.00304 0.00163 I1 0.19801 0.89634 0.53887 1.00000 0.04849 0.03702 0.03594 -0.00807 0.00575 0.00620 0.04048 0.00111 0.00014 0.00006 0.00003 0.00000 0.00036 0.00034 0.00028 0.00025 0.00027 0.00027 0.00021 Final Structure Factor Calculation for 2008lsh039 in P2(1)2(1)2(1) Total number of l.s. parameters = 101 Maximum vector length = 511 Memory required = 1403 / 26068 wR2 = 0.1264 before cycle 7 for 1755 data and 2 / 101 parameters GooF = S = 1.100; Restrained GooF = 1.100 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0364 * P )^2 + 5.67 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 R1 = 0.0459 for 1633 Fo > 4sig(Fo) and 0.0518 for all 1755 data wR2 = 0.1264, GooF = S = 1.100, Restrained GooF = 1.100 for all data Flack x parameter = 0.1221 with esd 0.0808 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 Occupancy sum of asymmetric unit = 11.00 for non-hydrogen and 8.00 for hydrogen atoms Principal mean square atomic displacements U 0.0330 0.0268 0.0195 C1 0.0429 0.0280 0.0154 C2 0.0371 0.0255 0.0213 C3 0.0419 0.0302 0.0244 C4 0.0580 0.0380 0.0256 C5 0.0377 0.0336 0.0235 C6 0.0349 0.0302 0.0238 C7 0.0474 0.0330 0.0230 C8 0.0340 0.0320 0.0273 N1 0.0584 0.0340 0.0255 O1 0.0516 0.0445 0.0253 I1 Analysis of variance for reflections employed in refinement K = Mean[Fo^2] / Mean[Fc^2] for group Fc/Fc(max) 0.000 0.034 0.053 0.071 0.089 0.104 0.125 0.153 0.195 0.264 1.000 Number in group 180. 173. 176. 186. 170. 170. 173. 177. 173. 177. GooF 1.149 1.066 1.035 1.089 1.268 1.065 1.015 0.846 1.010 1.374 K 1.083 1.002 1.011 1.010 1.006 0.990 0.984 1.016 1.021 1.020 Resolution(A) 0.77 0.81 0.86 0.90 0.95 1.01 1.08 1.19 1.36 1.69 inf Number in group 179. 185. 171. 171. 174. 172. 176. 175. 175. 177. GooF 1.241 1.309 1.108 1.006 1.133 0.911 0.827 1.022 0.940 1.357 K 1.091 1.067 1.041 1.025 0.992 0.999 1.007 0.999 1.015 1.019 R1 0.142 0.118 0.080 0.065 0.060 0.044 0.037 0.034 0.030 0.033 Recommended weighting scheme: WGHT 0.0361 5.6618 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 1 10 2043.06 3551.62 7.04 0.271 1.83 1 11 4 36.87 412.91 6.70 0.092 0.86 0 10 2 856.85 2129.84 6.65 0.210 0.97 0 1 5 2323.85 3966.34 6.63 0.286 3.48 -1 1 12 2963.29 4940.77 5.80 0.320 1.46 5 0 11 6.23 247.38 5.69 0.072 0.85 -2 1 1 2064.54 3438.77 5.63 0.267 2.36 -2 4 11 252.13 543.59 4.26 0.106 1.21 0 6 10 336.52 854.31 4.16 0.133 1.22 0 10 4 181.70 405.25 4.11 0.092 0.95 2 7 9 234.45 676.73 4.09 0.118 1.05 1 7 11 372.54 684.33 3.57 0.119 1.05 6 1 7 390.22 198.68 3.44 0.064 0.78 0 8 4 760.60 1160.92 3.43 0.155 1.18 0 2 14 485.66 761.42 3.42 0.125 1.28 -1 11 10 19.09 132.35 3.40 0.052 0.79 0 8 3 293.67 520.16 3.34 0.104 1.20 -1 9 10 484.36 757.55 3.19 0.125 0.92 4 1 17 539.06 320.72 3.16 0.081 0.81 4 4 16 141.27 33.25 3.11 0.026 0.80 2 4 11 283.51 511.49 3.08 0.103 1.21 0 3 23 175.77 327.17 2.85 0.082 0.79 0 10 3 170.19 309.01 2.81 0.080 0.96 3 7 13 66.57 6.41 2.76 0.012 0.85 0 2 4 1844.96 1466.49 2.76 0.174 3.37 2 0 20 91.68 0.33 2.72 0.003 0.87 -1 1 13 235.85 379.66 2.72 0.089 1.36 4 0 13 1233.96 1648.06 2.69 0.185 0.93 3 0 13 201.24 369.37 2.64 0.087 1.08 -3 5 8 150.50 262.31 2.63 0.074 1.10 3 2 13 635.77 884.38 2.54 0.135 1.05 5 2 12 659.71 453.35 2.53 0.097 0.82 4 2 14 182.79 88.24 2.49 0.043 0.89 2 4 21 69.42 168.00 2.43 0.059 0.79 4 6 13 630.41 412.61 2.41 0.092 0.81 6 1 1 187.07 70.64 2.40 0.038 0.81 1 9 7 313.51 499.17 2.39 0.102 0.98 4 5 11 102.19 196.29 2.37 0.064 0.89 4 4 15 646.42 467.45 2.35 0.098 0.82 5 2 11 -31.78 30.32 2.33 0.025 0.84 -2 4 7 1866.47 2454.26 2.32 0.225 1.45 1 0 1 -3.69 19.95 2.27 0.020 4.75 -1 11 8 95.30 199.25 2.25 0.064 0.82 1 11 6 22.43 84.87 2.24 0.042 0.84 6 0 1 628.47 411.16 2.23 0.092 0.82 0 1 8 9679.64 11390.34 2.22 0.485 2.26 5 5 11 669.55 493.30 2.21 0.101 0.78 6 3 1 151.31 66.30 2.20 0.037 0.79 -4 5 9 837.25 1074.95 2.20 0.149 0.93 -6 1 1 164.37 71.92 2.20 0.039 0.81 Bond lengths and angles C1 - Distance Angles C6 1.3794 (0.0123) C2 1.3920 (0.0115) 119.45 (0.78) N1 1.4042 (0.0111) 116.67 (0.76) 123.86 (0.78) C1 - C6 C2 C2 - Distance Angles C1 1.3920 (0.0115) C3 1.3974 (0.0124) 118.93 (0.77) H2 0.9500 120.54 120.54 C2 - C1 C3 C3 - Distance Angles C4 1.3754 (0.0124) C2 1.3974 (0.0124) 122.12 (0.78) I1 2.0968 (0.0081) 119.13 (0.61) 118.74 (0.64) C3 - C4 C2 C4 - Distance Angles C3 1.3754 (0.0124) C5 1.4070 (0.0129) 118.11 (0.82) H4 0.9500 120.95 120.95 C4 - C3 C5 C5 - Distance Angles C6 1.3814 (0.0148) C4 1.4070 (0.0129) 120.04 (0.86) H5 0.9500 119.98 119.98 C5 - C6 C4 C6 - Distance Angles C1 1.3794 (0.0123) C5 1.3814 (0.0148) 121.31 (0.82) H6 0.9500 119.35 119.35 C6 - C1 C5 C7 - Distance Angles O1 1.2430 (0.0110) N1 1.3434 (0.0116) 123.51 (0.91) C8 1.5054 (0.0131) 120.13 (0.83) 116.36 (0.77) C7 - O1 N1 C8 - Distance Angles C7 1.5054 (0.0132) 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 N1 - Distance Angles C7 1.3434 (0.0117) C1 1.4042 (0.0111) 128.58 (0.77) H1 0.8800 115.71 115.71 N1 - C7 C1 O1 - Distance Angles C7 1.2430 (0.0110) O1 - I1 - Distance Angles C3 2.0968 (0.0081) I1 - Specified hydrogen bonds (with esds except fixed and riding H) D-H H...A D...A <(DHA) 0.88 2.03 2.902(10) 174.1 N1-H1...O1_$1 Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A)