+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + SHELXL-97 - CRYSTAL STRUCTURE REFINEMENT - WinGX VERSION + + Copyright(C) George M. Sheldrick 1993-7 Release 97-2 + + 2008lsh038 started at 11:45:44 on 18-Jul-2008 + +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ TITL 2008lsh038 in Pna2(1) CELL 0.71073 10.5129 17.0435 4.0675 90.000 90.000 90.000 ZERR 4.00 0.0004 0.0004 0.0001 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 = 728.80 F(000) = 320.0 Mu = 0.10 mm-1 Cell Wt = 604.65 Rho = 1.378 MERG 2 OMIT -3.00 55.00 FMAP 2 PLAN 5 ACTA EQIV $1 -x+2, -y+1, z+1/2 EQIV $2 -x+3/2, y+1/2, z-1/2 HTAB N1 O2_$1 HTAB O2 O1_$2 HTAB SIZE 0.4 0.14 0.06 BOND $H L.S. 6 TEMP -153.00 WGHT 0.0257 0.2166 FVAR 2.11368 C1 1 0.809628 0.404632 0.266919 11.00000 0.01826 0.01642 = 0.01894 0.00144 0.00409 0.00117 C2 1 0.694985 0.390980 0.103933 11.00000 0.02070 0.01634 = 0.02255 -0.00190 0.00082 -0.00287 AFIX 43 H2 2 0.659180 0.339836 0.096140 11.00000 -1.20000 AFIX 0 C3 1 0.634355 0.453850 -0.046719 11.00000 0.01741 0.02294 = 0.02302 -0.00077 -0.00185 0.00003 AFIX 43 H3 2 0.556050 0.444981 -0.157208 11.00000 -1.20000 AFIX 0 C4 1 0.684352 0.529098 -0.041133 11.00000 0.02059 0.01871 = 0.02332 0.00251 0.00147 0.00338 AFIX 43 H4 2 0.641199 0.571180 -0.146097 11.00000 -1.20000 AFIX 0 C5 1 0.799581 0.541817 0.122106 11.00000 0.01835 0.01521 = 0.02311 0.00089 0.00452 0.00032 C6 1 0.861035 0.480091 0.274876 11.00000 0.01644 0.01765 = 0.01957 0.00095 0.00109 -0.00027 AFIX 43 H6 2 0.939064 0.489129 0.386428 11.00000 -1.20000 AFIX 0 C7 1 0.849908 0.271469 0.499060 11.00000 0.01955 0.01590 = 0.02258 0.00140 0.00461 0.00078 C8 1 0.946228 0.227066 0.700709 11.00000 0.02643 0.01735 = 0.02742 0.00391 0.00077 0.00081 AFIX 137 H8A 2 0.902032 0.191971 0.853602 11.00000 -1.50000 H8B 2 0.998555 0.264259 0.825087 11.00000 -1.50000 H8C 2 1.000736 0.196090 0.554574 11.00000 -1.50000 AFIX 0 N1 3 0.881002 0.346607 0.434049 11.00000 0.01731 0.01529 = 0.02168 0.00162 -0.00046 -0.00100 O1 4 0.751513 0.240071 0.397520 11.00000 0.02348 0.01693 = 0.03976 0.00546 -0.00237 -0.00413 O2 4 0.857153 0.613519 0.137312 11.00000 0.02029 0.01373 = 0.04145 0.00488 -0.00144 -0.00005 H1N 2 0.954657 0.361776 0.516228 11.00000 0.02209 H2O 2 0.809403 0.651984 0.049579 11.00000 0.04477 HKLF 4 1.0 0.00 1.00 0.00 0.00 0.00 1.00 1.00 0.00 0.00 Covalent radii and connectivity table for 2008lsh038 in Pna2(1) C 0.770 H 0.320 N 0.700 O 0.660 C1 - C2 C6 N1 C2 - C3 C1 C3 - C4 C2 C4 - C3 C5 C5 - O2 C6 C4 C6 - C5 C1 C7 - O1 N1 C8 C8 - C7 N1 - C7 C1 O1 - C7 O2 - C5 Operators for generating equivalent atoms: $1 -x+2, -y+1, z+1/2 $2 -x+3/2, y+1/2, z-1/2 Floating origin restraints generated 6471 Reflections read, of which 310 rejected -13 =< h =< 10, -21 =< k =< 22, -5 =< l =< 4, Max. 2-theta = 54.97 0 Systematic absence violations 0 Inconsistent equivalents 1555 Unique reflections, of which 0 suppressed R(int) = 0.0246 R(sigma) = 0.0282 Friedel opposites not merged Maximum memory for data reduction = 1288 / 15537 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 = 1583 / 140606 wR2 = 0.0716 before cycle 1 for 1555 data and 109 / 109 parameters GooF = S = 1.051; Restrained GooF = 1.051 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0257 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.11506 0.00417 0.331 OSF Mean shift/esd = 0.110 Maximum = 0.362 for x H1N Max. shift = 0.006 A for H1N Max. dU = 0.001 for H2O Least-squares cycle 2 Maximum vector length = 511 Memory required = 1583 / 140606 wR2 = 0.0715 before cycle 2 for 1555 data and 109 / 109 parameters GooF = S = 1.051; Restrained GooF = 1.050 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0257 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.11531 0.00416 0.062 OSF Mean shift/esd = 0.040 Maximum = 0.167 for x H1N Max. shift = 0.003 A for H1N Max. dU = 0.000 for H2O Least-squares cycle 3 Maximum vector length = 511 Memory required = 1583 / 140606 wR2 = 0.0715 before cycle 3 for 1555 data and 109 / 109 parameters GooF = S = 1.050; Restrained GooF = 1.050 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0257 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.11536 0.00416 0.010 OSF Mean shift/esd = 0.003 Maximum = 0.027 for x H1N Max. shift = 0.001 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 4 Maximum vector length = 511 Memory required = 1583 / 140606 wR2 = 0.0715 before cycle 4 for 1555 data and 109 / 109 parameters GooF = S = 1.050; Restrained GooF = 1.050 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0257 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.11537 0.00416 0.002 OSF Mean shift/esd = 0.001 Maximum = 0.007 for x H1N Max. shift = 0.000 A for H1N Max. dU = 0.000 for H1N Least-squares cycle 5 Maximum vector length = 511 Memory required = 1583 / 140606 wR2 = 0.0715 before cycle 5 for 1555 data and 109 / 109 parameters GooF = S = 1.050; Restrained GooF = 1.050 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0257 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.11537 0.00416 0.001 OSF Mean shift/esd = 0.000 Maximum = 0.001 for x H1N Max. shift = 0.000 A for H1N Max. dU = 0.000 for H2O Least-squares cycle 6 Maximum vector length = 511 Memory required = 1583 / 140606 wR2 = 0.0715 before cycle 6 for 1555 data and 109 / 109 parameters GooF = S = 1.050; Restrained GooF = 1.050 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0257 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 2.11537 0.00416 0.000 OSF Mean shift/esd = 0.000 Maximum = 0.000 for y O2 Max. shift = 0.000 A for H2O Max. dU = 0.000 for H2O 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 0.6592 0.3399 0.0962 43 0.950 0.000 C2 C3 C1 H3 0.5561 0.4450 -0.1572 43 0.950 0.000 C3 C4 C2 H4 0.6412 0.5712 -0.1460 43 0.950 0.000 C4 C3 C5 H6 0.9391 0.4891 0.3862 43 0.950 0.000 C6 C5 C1 H8A 0.9020 0.1919 0.8531 137 0.980 0.000 C8 C7 H8A H8B 0.9984 0.2643 0.8255 137 0.980 0.000 C8 C7 H8A H8C 1.0009 0.1962 0.5545 137 0.980 0.000 C8 C7 H8A 2008lsh038 in Pna2(1) ATOM x y z sof U11 U22 U33 U23 U13 U12 Ueq C1 0.80960 0.40464 0.26692 1.00000 0.01819 0.01661 0.01890 0.00143 0.00409 0.00129 0.01790 0.00234 0.00011 0.00007 0.00037 0.00000 0.00057 0.00054 0.00065 0.00054 0.00056 0.00046 0.00027 C2 0.69500 0.39100 0.10397 1.00000 0.02057 0.01639 0.02266 -0.00186 0.00103 -0.00294 0.01987 0.00236 0.00012 0.00007 0.00038 0.00000 0.00060 0.00053 0.00074 0.00057 0.00058 0.00046 0.00028 H2 0.65919 0.33986 0.09621 1.00000 0.02385 0.00000 0.00000 C3 0.63436 0.45384 -0.04670 1.00000 0.01734 0.02325 0.02298 -0.00079 -0.00174 -0.00001 0.02119 0.00242 0.00012 0.00007 0.00041 0.00000 0.00057 0.00061 0.00073 0.00061 0.00058 0.00047 0.00029 H3 0.55607 0.44497 -0.15724 1.00000 0.02543 0.00000 0.00000 C4 0.68436 0.52911 -0.04106 1.00000 0.02043 0.01885 0.02322 0.00256 0.00152 0.00348 0.02084 0.00244 0.00012 0.00007 0.00038 0.00000 0.00061 0.00056 0.00075 0.00056 0.00063 0.00046 0.00029 H4 0.64122 0.57120 -0.14597 1.00000 0.02500 0.00000 0.00000 C5 0.79956 0.54179 0.12217 1.00000 0.01833 0.01536 0.02299 0.00093 0.00456 0.00023 0.01890 0.00237 0.00012 0.00007 0.00037 0.00000 0.00058 0.00051 0.00072 0.00056 0.00056 0.00045 0.00028 C6 0.86103 0.48010 0.27481 1.00000 0.01641 0.01780 0.01964 0.00087 0.00111 -0.00026 0.01795 0.00230 0.00011 0.00007 0.00037 0.00000 0.00057 0.00055 0.00068 0.00052 0.00054 0.00043 0.00027 H6 0.93908 0.48914 0.38624 1.00000 0.02154 0.00000 0.00000 C7 0.84989 0.27145 0.49907 1.00000 0.01962 0.01609 0.02258 0.00131 0.00473 0.00081 0.01943 0.00237 0.00013 0.00007 0.00036 0.00000 0.00062 0.00054 0.00075 0.00050 0.00055 0.00047 0.00029 C8 0.94621 0.22707 0.70065 1.00000 0.02653 0.01732 0.02736 0.00382 0.00079 0.00074 0.02374 0.00255 0.00014 0.00008 0.00039 0.00000 0.00068 0.00055 0.00083 0.00055 0.00057 0.00048 0.00032 H8A 0.90203 0.19186 0.85310 1.00000 0.03560 0.00000 0.00000 H8B 0.99836 0.26427 0.82552 1.00000 0.03560 0.00000 0.00000 H8C 1.00088 0.19622 0.55446 1.00000 0.03560 0.00000 0.00000 N1 0.88101 0.34659 0.43407 1.00000 0.01740 0.01517 0.02178 0.00163 -0.00049 -0.00096 0.01812 0.00215 0.00010 0.00006 0.00036 0.00000 0.00048 0.00046 0.00059 0.00048 0.00048 0.00038 0.00023 O1 0.75153 0.24005 0.39749 1.00000 0.02343 0.01699 0.03966 0.00545 -0.00233 -0.00412 0.02670 0.00187 0.00009 0.00005 0.00034 0.00000 0.00046 0.00041 0.00061 0.00049 0.00045 0.00035 0.00024 O2 0.85718 0.61351 0.13727 1.00000 0.02040 0.01377 0.04147 0.00490 -0.00157 -0.00011 0.02521 0.00177 0.00009 0.00005 0.00031 0.00000 0.00046 0.00040 0.00069 0.00044 0.00046 0.00035 0.00026 H1N 0.95555 0.36177 0.51653 1.00000 0.02257 0.02967 0.00158 0.00087 0.00449 0.00000 0.00420 H2O 0.80908 0.65170 0.04993 1.00000 0.04607 0.03420 0.00188 0.00115 0.00563 0.00000 0.00589 Final Structure Factor Calculation for 2008lsh038 in Pna2(1) Total number of l.s. parameters = 109 Maximum vector length = 511 Memory required = 1476 / 25046 wR2 = 0.0715 before cycle 7 for 1555 data and 2 / 109 parameters GooF = S = 1.050; Restrained GooF = 1.050 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0257 * P )^2 + 0.22 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 R1 = 0.0306 for 1497 Fo > 4sig(Fo) and 0.0322 for all 1555 data wR2 = 0.0715, GooF = S = 1.050, Restrained GooF = 1.050 for all data Flack x parameter = 0.2171 with esd 1.1373 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 0.0232 0.0161 0.0144 C1 0.0243 0.0207 0.0147 C2 0.0241 0.0226 0.0168 C3 0.0261 0.0205 0.0159 C4 0.0259 0.0157 0.0151 C5 0.0202 0.0177 0.0159 C6 0.0263 0.0162 0.0158 C7 0.0290 0.0262 0.0160 C8 0.0223 0.0175 0.0145 N1 0.0415 0.0243 0.0143 O1 0.0424 0.0203 0.0129 O2 Analysis of variance for reflections employed in refinement K = Mean[Fo^2] / Mean[Fc^2] for group Fc/Fc(max) 0.000 0.047 0.069 0.087 0.109 0.131 0.161 0.198 0.247 0.359 1.000 Number in group 157. 162. 154. 159. 146. 160. 152. 153. 156. 156. GooF 1.114 1.041 1.051 1.044 1.046 1.024 1.057 0.969 0.920 1.211 K 0.980 0.970 0.992 1.006 0.995 1.004 1.007 1.003 1.009 1.003 Resolution(A) 0.77 0.80 0.83 0.87 0.92 0.98 1.05 1.16 1.32 1.67 inf Number in group 164. 157. 150. 154. 157. 152. 157. 152. 158. 154. GooF 1.152 1.069 1.065 0.873 0.854 0.986 0.961 0.879 1.093 1.436 K 1.049 1.036 1.024 0.986 1.002 0.997 0.992 1.001 1.011 1.003 R1 0.075 0.057 0.057 0.038 0.032 0.028 0.025 0.019 0.025 0.023 Recommended weighting scheme: WGHT 0.0239 0.2138 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) 2 1 0 806.57 931.33 3.86 0.627 5.02 8 17 1 27.49 15.34 3.68 0.080 0.78 5 2 0 56.05 41.91 3.65 0.133 2.04 5 8 0 5.09 10.00 3.42 0.065 1.50 4 3 0 16.08 23.53 3.26 0.100 2.39 3 6 0 1103.36 992.53 3.23 0.647 2.21 2 10 0 22.57 31.05 3.19 0.114 1.62 2 2 0 490.06 550.83 3.17 0.482 4.47 8 5 4 4.67 1.14 3.14 0.022 0.78 1 2 0 524.98 597.23 3.07 0.502 6.62 12 8 1 49.60 35.05 3.06 0.122 0.79 4 17 0 78.65 95.39 3.06 0.201 0.94 1 3 0 287.19 324.22 3.04 0.370 5.00 4 14 0 10.32 6.15 3.03 0.051 1.10 3 2 0 36.03 46.73 2.99 0.140 3.24 5 19 0 2.10 0.12 2.78 0.007 0.83 4 15 0 175.48 199.70 2.74 0.290 1.04 7 4 0 -0.39 1.22 2.74 0.023 1.42 10 0 -1 36.15 46.73 2.72 0.140 1.02 0 12 0 95.41 111.36 2.70 0.217 1.42 1 8 0 2.40 0.83 2.69 0.019 2.09 3 8 0 1558.45 1429.99 2.66 0.777 1.82 1 17 3 115.19 90.16 2.64 0.195 0.80 6 2 0 952.74 867.13 2.64 0.605 1.72 7 9 3 3.86 7.66 2.59 0.057 0.89 5 3 -1 212.15 188.75 2.56 0.282 1.77 2 3 0 2176.67 2371.17 2.56 1.000 3.86 7 17 -1 106.37 90.81 2.47 0.196 0.82 8 3 0 83.57 96.86 2.45 0.202 1.28 7 2 -2 77.07 89.87 2.43 0.195 1.20 5 3 1 210.49 189.07 2.42 0.282 1.77 6 0 -1 321.79 361.30 2.41 0.390 1.61 1 10 0 274.36 248.60 2.41 0.324 1.68 5 19 1 52.76 42.67 2.36 0.134 0.81 4 2 1 36.61 29.92 2.33 0.112 2.14 9 10 2 28.93 19.68 2.31 0.091 0.87 11 9 2 59.35 44.61 2.29 0.137 0.79 8 15 -1 36.32 28.03 2.29 0.109 0.84 7 13 -1 23.22 29.45 2.28 0.111 0.96 6 16 0 68.19 80.31 2.27 0.184 0.91 1 4 -2 396.37 363.46 2.26 0.392 1.81 4 2 -1 36.41 29.91 2.25 0.112 2.14 8 3 -4 25.99 34.65 2.24 0.121 0.80 8 15 0 32.16 40.40 2.22 0.131 0.86 2 13 4 28.99 39.26 2.22 0.129 0.79 4 16 0 77.57 89.10 2.22 0.194 0.99 3 7 0 1.71 3.63 2.22 0.039 2.00 8 17 -1 23.37 15.32 2.21 0.080 0.78 8 0 -1 81.08 69.08 2.18 0.171 1.25 11 12 0 2.15 0.01 2.17 0.002 0.79 Bond lengths and angles C1 - Distance Angles C2 1.3946 (0.0019) C6 1.3954 (0.0017) 119.95 (0.12) N1 1.4160 (0.0018) 124.73 (0.11) 115.32 (0.12) C1 - C2 C6 C2 - Distance Angles C3 1.3889 (0.0019) C1 1.3946 (0.0019) 118.53 (0.11) H2 0.9500 120.73 120.73 C2 - C3 C1 C3 - Distance Angles C4 1.3864 (0.0017) C2 1.3889 (0.0019) 122.15 (0.13) H3 0.9500 118.92 118.92 C3 - C4 C2 C4 - Distance Angles C3 1.3864 (0.0017) C5 1.3979 (0.0019) 118.65 (0.12) H4 0.9500 120.68 120.68 C4 - C3 C5 C5 - Distance Angles O2 1.3655 (0.0015) C6 1.3815 (0.0018) 116.97 (0.12) C4 1.3979 (0.0019) 122.96 (0.12) 120.06 (0.11) C5 - O2 C6 C6 - Distance Angles C5 1.3815 (0.0018) C1 1.3954 (0.0017) 120.65 (0.12) H6 0.9500 119.67 119.67 C6 - C5 C1 C7 - Distance Angles O1 1.2355 (0.0016) N1 1.3478 (0.0016) 123.31 (0.13) C8 1.5066 (0.0019) 121.80 (0.11) 114.87 (0.12) C7 - O1 N1 C8 - Distance Angles C7 1.5066 (0.0019) 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 1.3478 (0.0016) C1 1.4160 (0.0018) 129.01 (0.12) H1N 0.8908 (0.0170) 114.56 (1.01) 116.37 (1.00) N1 - C7 C1 O1 - Distance Angles C7 1.2355 (0.0017) O1 - O2 - Distance Angles C5 1.3655 (0.0015) H2O 0.8975 (0.0209) 112.43 (1.22) O2 - C5 Specified hydrogen bonds (with esds except fixed and riding H) D-H H...A D...A <(DHA) 0.891(17) 2.072(17) 2.9532(15) 169.7(16) N1-H1N...O2_$1 0.90(2) 1.75(2) 2.6285(13) 166.0(18) O2-H2O...O1_$2 Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. D-H d(D-H) d(H..A)