+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + SHELXL-97 - CRYSTAL STRUCTURE REFINEMENT - WinGX VERSION + + Copyright(C) George M. Sheldrick 1993-7 Release 97-2 + + shelxl started at 17:30:15 on 31-Mar-2009 + +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ TITL 2008lsh024 in Pnma CELL 0.71073 8.5936 7.2391 9.1897 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0002 0.0003 0.000 0.000 0.000 LATT 1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, - Z SYMM 1/2 + X, 1/2 - Y, 1/2 - Z SFAC C H N CL UNIT 24 24 4 4 V = 571.69 F(000) = 264.0 Mu = 0.54 mm-1 Cell Wt = 510.27 Rho = 1.482 MERG 2 OMIT -3.00 55.00 FMAP 2 PLAN 5 SIZE 0.12 0.16 0.16 ACTA EQIV $1 -x+1/2, -y, z-1/2 HTAB N1 Cl1_$1 HTAB BOND $H DFIX 0.88 0.02 N1 H1N L.S. 6 TEMP -153.00 WGHT 0.027000 0.217800 FVAR 1.15616 C1 1 0.121065 0.250000 0.395382 10.50000 0.01433 0.02262 = 0.01305 0.00000 0.00212 0.00000 C2 1 0.184862 0.083374 0.444975 11.00000 0.01735 0.01738 = 0.01700 -0.00264 0.00094 -0.00141 AFIX 43 H2 2 0.142483 -0.030517 0.412307 11.00000 -1.20000 AFIX 0 C3 1 0.309708 0.082822 0.541625 11.00000 0.01660 0.01596 = 0.01674 0.00091 0.00207 0.00160 AFIX 43 H3 2 0.352468 -0.030536 0.575000 11.00000 -1.20000 AFIX 0 C4 1 0.370868 0.250000 0.588569 10.50000 0.01304 0.01986 = 0.01209 0.00000 0.00015 0.00000 N1 3 0.000995 0.250000 0.293697 10.50000 0.02239 0.02238 = 0.02466 0.00000 -0.00822 0.00000 CL1 4 0.530944 0.250000 0.706426 10.50000 0.01653 0.02013 = 0.01711 0.00000 -0.00339 0.00000 H1N 2 -0.052521 0.149459 0.286372 11.00000 0.03621 HKLF 4 1.0 0.00 1.00 0.00 1.00 0.00 0.00 0.00 0.00 -1.00 Covalent radii and connectivity table for 2008lsh024 in Pnma C 0.770 H 0.320 N 0.700 CL 0.990 C1 - N1 C2_$2 C2 C2 - C3 C1 C3 - C4 C2 C4 - C3 C3_$2 Cl1 N1 - C1 Cl1 - C4 Operators for generating equivalent atoms: $1 -x+1/2, -y, z-1/2 $2 x, -y+1/2, z 5685 Reflections read, of which 368 rejected -11 =< h =< 9, -9 =< k =< 9, -11 =< l =< 9, Max. 2-theta = 54.96 0 Systematic absence violations 0 Inconsistent equivalents 704 Unique reflections, of which 0 suppressed R(int) = 0.0247 R(sigma) = 0.0207 Friedel opposites merged Maximum memory for data reduction = 825 / 6991 Special position constraints for C1 y = 0.2500 U23 = 0 U12 = 0 sof = 0.50000 Input constraints retained (at least in part) for sof Special position constraints for C4 y = 0.2500 U23 = 0 U12 = 0 sof = 0.50000 Input constraints retained (at least in part) for sof Special position constraints for N1 y = 0.2500 U23 = 0 U12 = 0 sof = 0.50000 Input constraints retained (at least in part) for sof Special position constraints for Cl1 y = 0.2500 U23 = 0 U12 = 0 sof = 0.50000 Input constraints retained (at least in part) for sof 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 = 962 / 72251 wR2 = 0.0655 before cycle 1 for 704 data and 47 / 47 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 0.016 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.189; Restrained GooF = 1.189 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0270 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.15126 0.00310 -1.582 OSF Mean shift/esd = 0.181 Maximum = -1.582 for OSF Max. shift = 0.009 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 2 Maximum vector length = 511 Memory required = 962 / 72251 wR2 = 0.0655 before cycle 2 for 704 data and 47 / 47 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 0.008 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.188; Restrained GooF = 1.187 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0270 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.15031 0.00309 -0.308 OSF Mean shift/esd = 0.058 Maximum = -0.308 for OSF Max. shift = 0.003 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 3 Maximum vector length = 511 Memory required = 962 / 72251 wR2 = 0.0655 before cycle 3 for 704 data and 47 / 47 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 0.005 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.188; Restrained GooF = 1.187 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0270 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.15030 0.00309 -0.003 OSF Mean shift/esd = 0.001 Maximum = 0.005 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 = 962 / 72251 wR2 = 0.0655 before cycle 4 for 704 data and 47 / 47 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 0.005 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.188; Restrained GooF = 1.187 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0270 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.15030 0.00309 0.000 OSF Mean shift/esd = 0.000 Maximum = 0.001 for z C4 Max. shift = 0.000 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 5 Maximum vector length = 511 Memory required = 962 / 72251 wR2 = 0.0655 before cycle 5 for 704 data and 47 / 47 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 0.005 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.188; Restrained GooF = 1.187 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0270 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.15030 0.00309 0.000 OSF Mean shift/esd = 0.000 Maximum = 0.000 for z Cl1 Max. shift = 0.000 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 6 Maximum vector length = 511 Memory required = 962 / 72251 wR2 = 0.0655 before cycle 6 for 704 data and 47 / 47 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 0.005 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.188; Restrained GooF = 1.187 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0270 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 1.15030 0.00309 0.000 OSF Mean shift/esd = 0.000 Maximum = 0.000 for z Cl1 Max. shift = 0.000 A for H1N Max. dU = 0.000 for Cl1 Largest correlation matrix elements 0.584 U11 Cl1 / OSF 0.575 U33 Cl1 / OSF 0.572 U22 Cl1 / OSF Idealized hydrogen atom generation before cycle 7 Name x y z AFIX d(X-H) shift Bonded to Conformation determined by H2 0.1425 -0.0305 0.4123 43 0.950 0.000 C2 C3 C1 H3 0.3524 -0.0305 0.5750 43 0.950 0.000 C3 C4 C2 2008lsh024 in Pnma ATOM x y z sof U11 U22 U33 U23 U13 U12 Ueq C1 0.12107 0.25000 0.39538 0.50000 0.01415 0.02243 0.01285 0.00000 0.00209 0.00000 0.01648 0.00211 0.00017 0.00000 0.00016 0.00000 0.00066 0.00078 0.00070 0.00000 0.00056 0.00000 0.00033 C2 0.18487 0.08337 0.44496 1.00000 0.01717 0.01719 0.01682 -0.00262 0.00092 -0.00141 0.01706 0.00185 0.00012 0.00016 0.00011 0.00000 0.00048 0.00054 0.00053 0.00041 0.00039 0.00040 0.00025 H2 0.14250 -0.03052 0.41228 1.00000 0.02047 0.00000 0.00000 C3 0.30970 0.08281 0.54162 1.00000 0.01640 0.01579 0.01656 0.00090 0.00205 0.00160 0.01625 0.00189 0.00012 0.00015 0.00011 0.00000 0.00048 0.00052 0.00053 0.00039 0.00038 0.00040 0.00025 H3 0.35244 -0.03054 0.57501 1.00000 0.01950 0.00000 0.00000 C4 0.37086 0.25000 0.58855 0.50000 0.01288 0.01965 0.01189 0.00000 0.00014 0.00000 0.01481 0.00204 0.00016 0.00000 0.00016 0.00000 0.00065 0.00075 0.00069 0.00000 0.00053 0.00000 0.00031 N1 0.00100 0.25000 0.29369 0.50000 0.02218 0.02239 0.02447 0.00000 -0.00823 0.00000 0.02302 0.00211 0.00020 0.00000 0.00016 0.00000 0.00068 0.00080 0.00084 0.00000 0.00057 0.00000 0.00034 Cl1 0.53095 0.25000 0.70643 0.50000 0.01631 0.01993 0.01690 0.00000 -0.00339 0.00000 0.01772 0.00049 0.00004 0.00000 0.00004 0.00000 0.00022 0.00023 0.00023 0.00000 0.00013 0.00000 0.00015 H1N -0.05282 0.14777 0.28616 1.00000 0.03691 0.02392 0.00176 0.00208 0.00162 0.00000 0.00469 Final Structure Factor Calculation for 2008lsh024 in Pnma Total number of l.s. parameters = 47 Maximum vector length = 511 Memory required = 915 / 22995 wR2 = 0.0655 before cycle 7 for 704 data and 0 / 47 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 0.005 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 0.000 GooF = S = 1.188; Restrained GooF = 1.187 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0270 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 R1 = 0.0244 for 678 Fo > 4sig(Fo) and 0.0254 for all 704 data wR2 = 0.0655, GooF = S = 1.188, Restrained GooF = 1.187 for all data Occupancy sum of asymmetric unit = 4.00 for non-hydrogen and 3.00 for hydrogen atoms Principal mean square atomic displacements U 0.0224 0.0157 0.0113 C1 0.0205 0.0164 0.0143 C2 0.0194 0.0152 0.0141 C3 0.0197 0.0129 0.0119 C4 0.0316 0.0224 0.0150 N1 0.0200 0.0199 0.0132 Cl1 Analysis of variance for reflections employed in refinement K = Mean[Fo^2] / Mean[Fc^2] for group Fc/Fc(max) 0.000 0.021 0.040 0.059 0.084 0.107 0.132 0.164 0.207 0.269 1.000 Number in group 71. 73. 67. 75. 68. 69. 73. 69. 68. 71. GooF 1.489 1.165 1.246 1.241 0.837 1.053 1.240 0.726 1.353 1.303 K 1.378 0.922 0.953 0.977 1.005 0.997 1.001 1.002 1.014 0.991 Resolution(A) 0.77 0.80 0.83 0.87 0.92 0.98 1.05 1.17 1.35 1.71 inf Number in group 75. 70. 68. 71. 71. 69. 70. 69. 70. 71. GooF 1.304 1.290 0.998 0.869 0.939 1.027 0.840 0.954 1.234 1.965 K 0.994 1.003 1.011 1.012 0.998 1.010 1.002 0.999 1.017 0.977 R1 0.055 0.039 0.025 0.024 0.025 0.022 0.016 0.016 0.021 0.027 Recommended weighting scheme: WGHT 0.0240 0.2161 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) 3 1 2 6.24 1.09 5.57 0.012 2.30 3 3 1 529.20 439.38 4.62 0.239 1.81 1 3 3 499.53 423.22 4.08 0.235 1.85 4 0 3 244.54 200.43 4.05 0.162 1.76 10 0 4 4.85 13.02 3.99 0.041 0.80 0 2 4 4.74 11.35 3.92 0.038 1.94 3 5 3 13.42 21.38 3.24 0.053 1.19 2 6 4 27.19 37.84 2.96 0.070 1.04 3 7 3 11.57 18.42 2.96 0.049 0.93 0 0 2 77.52 61.46 2.93 0.089 4.59 2 0 5 824.82 735.41 2.92 0.309 1.69 2 2 1 113.37 134.27 2.85 0.132 2.65 8 2 7 37.97 28.29 2.70 0.061 0.81 7 7 1 5.20 2.08 2.69 0.016 0.79 6 0 5 82.52 99.87 2.67 0.114 1.13 3 3 3 378.03 337.02 2.64 0.209 1.58 0 2 0 4040.14 4478.83 2.58 0.764 3.62 1 7 7 8.63 13.88 2.53 0.043 0.81 0 6 6 77.17 94.28 2.50 0.111 0.95 6 1 9 3.16 0.26 2.48 0.006 0.83 4 6 0 156.35 134.62 2.48 0.132 1.05 1 3 1 897.34 819.67 2.43 0.327 2.25 8 0 7 38.30 49.23 2.43 0.080 0.83 2 4 2 537.03 591.52 2.39 0.278 1.57 10 2 4 4.25 7.81 2.33 0.032 0.79 4 8 3 173.15 151.27 2.31 0.140 0.80 6 6 6 6.13 10.33 2.26 0.037 0.79 4 7 6 1.80 4.86 2.25 0.025 0.80 0 2 2 5633.47 6138.68 2.25 0.894 2.84 2 4 9 2.20 4.96 2.24 0.025 0.87 2 7 6 1.94 0.07 2.21 0.003 0.84 5 7 2 27.45 34.83 2.21 0.067 0.87 7 5 6 4.59 2.14 2.19 0.017 0.80 0 4 4 1.65 0.26 2.16 0.006 1.42 8 4 4 3.01 0.79 2.13 0.010 0.86 6 0 6 39.51 31.74 2.10 0.064 1.05 1 3 5 378.77 345.94 2.09 0.212 1.44 4 4 1 185.72 206.41 2.07 0.164 1.37 3 5 2 5.27 2.91 2.06 0.019 1.24 1 1 3 384.22 351.94 2.04 0.214 2.68 1 7 5 75.24 87.23 2.00 0.107 0.90 8 6 1 229.71 204.37 1.98 0.163 0.80 9 4 1 10.44 15.03 1.96 0.044 0.84 7 1 4 40.87 48.55 1.92 0.080 1.07 3 9 1 48.83 39.74 1.90 0.072 0.77 2 4 1 9.60 13.32 1.90 0.042 1.64 7 7 2 34.30 41.77 1.89 0.074 0.78 6 2 8 0.65 2.38 1.87 0.018 0.87 1 3 2 1253.79 1174.35 1.82 0.391 2.07 0 3 1 772.42 828.34 1.76 0.328 2.33 Bond lengths and angles C1 - Distance Angles N1 1.3922 (0.0021) C2_$2 1.4012 (0.0013) 120.55 (0.07) C2 1.4012 (0.0013) 120.55 (0.07) 118.83 (0.14) C1 - N1 C2_$2 C2 - Distance Angles C3 1.3927 (0.0015) C1 1.4012 (0.0013) 120.75 (0.10) H2 0.9500 119.63 119.63 C2 - C3 C1 C3 - Distance Angles C4 1.3882 (0.0013) C2 1.3927 (0.0015) 119.16 (0.10) H3 0.9500 120.42 120.42 C3 - C4 C2 C4 - Distance Angles C3 1.3882 (0.0013) C3_$2 1.3882 (0.0013) 121.35 (0.14) Cl1 1.7510 (0.0015) 119.32 (0.07) 119.32 (0.07) C4 - C3 C3_$2 N1 - Distance Angles C1 1.3922 (0.0021) H1N 0.8754 (0.0134) 116.40 (1.06) N1 - C1 Cl1 - Distance Angles C4 1.7510 (0.0015) Cl1 - Specified hydrogen bonds (with esds except fixed and riding H) D-H H...A D...A <(DHA) 0.875(13) 2.977(15) 3.7175(4) 143.5(13) N1-H1N...Cl1_$1 Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A)