+++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + SHELXL-97 - CRYSTAL STRUCTURE REFINEMENT - WinGX VERSION + + Copyright(C) George M. Sheldrick 1993-7 Release 97-2 + + 2009src0246p21c started at 13:05:41 on 06-Apr-2009 + +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ TITL 2009src0246p21c in P2(1)/c CELL 0.71073 10.8836 8.4697 7.9738 90.000 102.651 90.000 ZERR 4.00 0.0011 0.0009 0.0007 0.000 0.006 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O F CL UNIT 24 12 4 4 12 4 V = 717.19 F(000) = 392.0 Mu = 0.53 mm-1 Cell Wt = 790.18 Rho = 1.830 MERG 2 OMIT -3.00 55.00 SHEL 7 0.77 FMAP 2 PLAN 10 SIZE 0.17 0.23 0.33 ACTA BOND $H WGHT 0.07000 0.02430 L.S. 4 TEMP -153.00 FVAR 0.18383 MOLE 1 C2 1 0.197423 0.381962 -0.026444 11.00000 0.02959 0.02738 = 0.03000 0.00346 0.00619 0.00143 AFIX 43 H2 2 0.198348 0.269953 -0.032310 11.00000 -1.20000 AFIX 0 C3 1 0.290913 0.458772 0.083674 11.00000 0.02483 0.03184 = 0.02586 0.00158 0.00519 0.00300 C4 1 0.288054 0.625397 0.089442 11.00000 0.02775 0.02950 = 0.02773 -0.00435 0.00377 -0.00600 AFIX 43 H4 2 0.353173 0.681401 0.164896 11.00000 -1.20000 AFIX 0 C5 1 0.191969 0.705496 -0.013153 11.00000 0.03012 0.02316 = 0.02885 -0.00159 0.00785 -0.00185 C6 1 0.090057 0.626539 -0.130376 11.00000 0.02711 0.02525 = 0.03012 0.00242 0.00844 -0.00012 C7 1 0.395662 0.368998 0.191976 11.00000 0.03308 0.03834 = 0.03157 0.00274 0.00289 0.00207 N1 3 0.102511 0.463987 -0.128368 11.00000 0.02668 0.02469 = 0.03107 -0.00071 -0.00106 -0.00191 AFIX 43 H1 2 0.044284 0.409417 -0.198751 11.00000 -1.20000 AFIX 0 O6 4 -0.000208 0.691935 -0.224717 11.00000 0.02910 0.02985 = 0.04227 0.00434 -0.00356 0.00529 F7B 5 0.423685 0.420056 0.353970 11.00000 0.06368 0.07637 = 0.03220 -0.00789 -0.01168 0.02678 F7C 5 0.503818 0.379783 0.136980 11.00000 0.03009 0.06642 = 0.06062 0.02272 0.00915 0.01174 CL5 6 0.183436 0.908653 -0.010981 11.00000 0.04917 0.02323 = 0.04449 -0.00233 0.00946 -0.00195 F7A 5 0.371991 0.214498 0.198821 11.00000 0.04577 0.03787 = 0.06204 0.01561 -0.00516 0.00372 HKLF 4 Covalent radii and connectivity table for 2009src0246p21c in P2(1)/c C 0.770 H 0.320 N 0.700 O 0.660 F 0.640 CL 0.990 C2 - C3 N1 C3 - C2 C4 C7 C4 - C5 C3 C5 - C4 C6 Cl5 C6 - O6 N1 C5 C7 - F7B F7A F7C C3 N1 - C2 C6 O6 - C6 F7B - C7 F7C - C7 Cl5 - C5 F7A - C7 10120 Reflections read, of which 466 rejected -14 =< h =< 14, -10 =< k =< 10, -10 =< l =< 10, Max. 2-theta = 54.94 0 Systematic absence violations Inconsistent equivalents etc. h k l Fo^2 Sigma(Fo^2) N Su of mean(Fo^2) -5 1 4 8.24 0.29 10 1.92 1 Inconsistent equivalents 1630 Unique reflections, of which 0 suppressed R(int) = 0.0624 R(sigma) = 0.0520 Friedel opposites merged Maximum memory for data reduction = 1023 / 16190 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 = 1294 / 142650 wR2 = 0.1290 before cycle 1 for 1630 data and 109 / 109 parameters GooF = S = 1.054; Restrained GooF = 1.054 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0700 * P )^2 + 0.02 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value su shift/su parameter 1 0.18385 0.00065 0.024 OSF Mean shift/su = 0.010 Maximum = -0.036 for z F7B Max. shift = 0.000 A for C7 Max. dU = 0.000 for C3 Least-squares cycle 2 Maximum vector length = 511 Memory required = 1294 / 142650 wR2 = 0.1290 before cycle 2 for 1630 data and 109 / 109 parameters GooF = S = 1.054; Restrained GooF = 1.054 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0700 * P )^2 + 0.02 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value su shift/su parameter 1 0.18384 0.00065 -0.001 OSF Mean shift/su = 0.003 Maximum = -0.011 for z F7B Max. shift = 0.000 A for C7 Max. dU = 0.000 for C3 Least-squares cycle 3 Maximum vector length = 511 Memory required = 1294 / 142650 wR2 = 0.1290 before cycle 3 for 1630 data and 109 / 109 parameters GooF = S = 1.054; Restrained GooF = 1.054 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0700 * P )^2 + 0.02 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value su shift/su parameter 1 0.18384 0.00065 0.000 OSF Mean shift/su = 0.000 Maximum = -0.001 for x F7C Max. shift = 0.000 A for C5 Max. dU = 0.000 for C3 Least-squares cycle 4 Maximum vector length = 511 Memory required = 1294 / 142650 wR2 = 0.1290 before cycle 4 for 1630 data and 109 / 109 parameters GooF = S = 1.054; Restrained GooF = 1.054 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0700 * P )^2 + 0.02 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value su shift/su parameter 1 0.18384 0.00065 0.000 OSF Mean shift/su = 0.000 Maximum = 0.000 for y F7A Max. shift = 0.000 A for H4 Max. dU = 0.000 for O6 Largest correlation matrix elements 0.508 U22 Cl5 / OSF 0.506 U33 Cl5 / OSF Idealized hydrogen atom generation before cycle 5 Name x y z AFIX d(X-H) shift Bonded to Conformation determined by H2 0.1983 0.2700 -0.0323 43 0.950 0.000 C2 C3 N1 H4 0.3532 0.6814 0.1649 43 0.950 0.000 C4 C5 C3 H1 0.0443 0.4094 -0.1987 43 0.880 0.000 N1 C2 C6 2009src0246p21c in P2(1)/c ATOM x y z sof U11 U22 U33 U23 U13 U12 Ueq C2 0.19742 0.38197 -0.02645 1.00000 0.02960 0.02734 0.02997 0.00348 0.00619 0.00145 0.02902 0.00461 0.00022 0.00030 0.00030 0.00000 0.00135 0.00144 0.00129 0.00101 0.00110 0.00102 0.00060 H2 0.19835 0.26996 -0.03231 1.00000 0.03483 0.00000 0.00000 C3 0.29092 0.45877 0.08367 1.00000 0.02483 0.03180 0.02584 0.00159 0.00518 0.00300 0.02755 0.00468 0.00022 0.00029 0.00030 0.00000 0.00127 0.00138 0.00124 0.00106 0.00105 0.00104 0.00056 C4 0.28805 0.62540 0.08944 1.00000 0.02773 0.02952 0.02770 -0.00436 0.00377 -0.00601 0.02867 0.00457 0.00022 0.00028 0.00031 0.00000 0.00131 0.00138 0.00124 0.00107 0.00107 0.00105 0.00057 H4 0.35317 0.68141 0.16489 1.00000 0.03440 0.00000 0.00000 C5 0.19196 0.70550 -0.01315 1.00000 0.03013 0.02314 0.02882 -0.00158 0.00785 -0.00184 0.02715 0.00436 0.00021 0.00029 0.00029 0.00000 0.00134 0.00124 0.00123 0.00101 0.00108 0.00101 0.00055 C6 0.09006 0.62654 -0.13037 1.00000 0.02709 0.02525 0.03010 0.00242 0.00845 -0.00010 0.02714 0.00453 0.00022 0.00027 0.00031 0.00000 0.00127 0.00130 0.00127 0.00104 0.00108 0.00100 0.00055 C7 0.39567 0.36900 0.19198 1.00000 0.03308 0.03834 0.03156 0.00272 0.00287 0.00204 0.03497 0.00497 0.00024 0.00030 0.00033 0.00000 0.00141 0.00153 0.00137 0.00119 0.00111 0.00118 0.00062 N1 0.10251 0.46398 -0.12837 1.00000 0.02668 0.02468 0.03108 -0.00071 -0.00106 -0.00191 0.02861 0.00380 0.00018 0.00023 0.00025 0.00000 0.00113 0.00111 0.00110 0.00091 0.00090 0.00086 0.00049 H1 0.04428 0.40941 -0.19874 1.00000 0.03434 0.00000 0.00000 O6 -0.00021 0.69193 -0.22472 1.00000 0.02909 0.02984 0.04227 0.00433 -0.00355 0.00529 0.03547 0.00327 0.00016 0.00020 0.00022 0.00000 0.00096 0.00094 0.00102 0.00082 0.00081 0.00081 0.00045 F7B 0.42368 0.42005 0.35396 1.00000 0.06368 0.07636 0.03219 -0.00789 -0.01167 0.02678 0.06081 0.00318 0.00016 0.00020 0.00020 0.00000 0.00122 0.00129 0.00090 0.00080 0.00082 0.00095 0.00056 F7C 0.50381 0.37978 0.13698 1.00000 0.03008 0.06644 0.06060 0.02272 0.00916 0.01175 0.05249 0.00328 0.00014 0.00019 0.00022 0.00000 0.00086 0.00119 0.00107 0.00087 0.00077 0.00077 0.00050 Cl5 0.18344 0.90865 -0.01098 1.00000 0.04918 0.02324 0.04449 -0.00233 0.00946 -0.00195 0.03909 0.00124 0.00006 0.00007 0.00009 0.00000 0.00046 0.00036 0.00043 0.00027 0.00033 0.00028 0.00026 F7A 0.37199 0.21450 0.19882 1.00000 0.04577 0.03784 0.06203 0.01559 -0.00514 0.00373 0.05115 0.00312 0.00015 0.00018 0.00021 0.00000 0.00096 0.00096 0.00107 0.00081 0.00080 0.00076 0.00047 Final Structure Factor Calculation for 2009src0246p21c in P2(1)/c Total number of l.s. parameters = 109 Maximum vector length = 511 Memory required = 1185 / 25039 wR2 = 0.1290 before cycle 5 for 1630 data and 0 / 109 parameters GooF = S = 1.054; Restrained GooF = 1.054 for 0 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0700 * P )^2 + 0.02 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 R1 = 0.0513 for 1154 Fo > 4sig(Fo) and 0.0826 for all 1630 data wR2 = 0.1290, GooF = S = 1.054, Restrained GooF = 1.054 for all data Occupancy sum of asymmetric unit = 12.00 for non-hydrogen and 3.00 for hydrogen atoms Principal mean square atomic displacements U 0.0324 0.0299 0.0248 C2 0.0330 0.0261 0.0236 C3 0.0348 0.0305 0.0207 C4 0.0314 0.0276 0.0225 C5 0.0315 0.0264 0.0235 C6 0.0393 0.0377 0.0279 C7 0.0387 0.0257 0.0215 N1 0.0520 0.0339 0.0205 O6 0.1091 0.0489 0.0244 F7B 0.0865 0.0448 0.0262 F7C 0.0496 0.0447 0.0229 Cl5 0.0810 0.0460 0.0265 F7A Analysis of variance for reflections employed in refinement K = Mean[Fo^2] / Mean[Fc^2] for group Fc/Fc(max) 0.000 0.007 0.014 0.020 0.028 0.036 0.045 0.061 0.085 0.119 1.000 Number in group 175. 179. 139. 178. 159. 149. 163. 164. 162. 162. GooF 1.012 1.055 1.088 0.942 1.189 1.087 1.176 0.981 1.000 1.004 K 7.751 1.824 1.211 1.028 0.969 0.979 0.977 1.000 1.029 1.015 Resolution(A) 0.77 0.80 0.83 0.87 0.92 0.97 1.05 1.15 1.32 1.66 inf Number in group 166. 163. 167. 159. 161. 166. 159. 166. 160. 163. GooF 0.955 0.898 1.041 1.046 1.009 1.122 1.056 1.172 1.067 1.143 K 1.121 1.087 1.062 1.054 1.049 1.024 1.065 1.053 1.049 0.981 R1 0.265 0.227 0.180 0.117 0.103 0.082 0.059 0.048 0.035 0.030 Recommended weighting scheme: WGHT 0.0697 0.0284 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)/su Fc/Fc(max) Resolution(A) 5 3 1 10.49 3.05 4.02 0.010 1.60 -4 1 3 11.80 6.42 3.60 0.014 2.04 -4 1 9 57.70 92.19 3.43 0.053 0.88 -8 7 4 33.93 68.10 3.31 0.046 0.86 8 0 2 4974.57 3715.46 3.28 0.339 1.18 -1 8 2 21.17 35.67 3.21 0.033 1.02 -4 6 3 42.08 77.23 3.19 0.049 1.17 -4 4 1 -0.11 4.97 3.18 0.012 1.67 10 6 0 31.23 4.90 3.17 0.012 0.85 -9 1 5 24.92 41.45 3.12 0.036 1.05 -1 6 3 8.46 0.21 3.08 0.003 1.25 3 3 7 22.81 46.11 2.96 0.038 0.94 -4 6 1 32.86 45.50 2.89 0.037 1.25 -5 3 7 7.62 15.44 2.85 0.022 1.01 2 2 4 36.96 28.47 2.76 0.030 1.59 1 5 0 232.35 186.53 2.74 0.076 1.67 -5 3 1 52.78 40.57 2.72 0.035 1.72 7 5 4 17.89 42.68 2.72 0.036 0.91 2 3 1 3.61 0.03 2.71 0.001 2.31 -6 0 8 11.02 34.00 2.68 0.032 0.94 -1 9 2 645.01 519.69 2.65 0.127 0.92 1 1 6 24.61 32.84 2.65 0.032 1.24 1 10 1 83.23 47.25 2.65 0.038 0.84 -9 2 5 637.71 519.26 2.62 0.127 1.03 1 3 3 51.45 40.96 2.61 0.036 1.83 -1 5 2 40.61 53.40 2.59 0.041 1.56 -7 2 4 75.22 94.07 2.57 0.054 1.28 -8 1 7 112.59 80.54 2.55 0.050 0.96 5 1 1 4541.20 3777.24 2.50 0.341 1.89 -4 3 6 141.23 176.23 2.45 0.074 1.17 -6 2 2 109.94 133.86 2.42 0.064 1.63 10 0 0 2569.89 2101.88 2.40 0.255 1.06 8 1 3 341.63 277.30 2.39 0.093 1.08 3 5 4 7.31 20.10 2.38 0.025 1.15 -7 0 6 2342.87 1939.91 2.36 0.245 1.11 3 1 7 91.51 117.16 2.34 0.060 0.99 -3 4 5 46.85 62.37 2.34 0.044 1.25 10 2 3 186.52 145.80 2.33 0.067 0.89 9 1 1 32.47 45.33 2.32 0.037 1.12 3 6 2 199.38 144.50 2.31 0.067 1.21 -6 1 4 18.79 24.84 2.30 0.028 1.46 -1 7 2 282.28 340.09 2.29 0.102 1.16 9 4 3 59.58 96.17 2.28 0.054 0.90 -9 6 6 24.54 0.06 2.28 0.001 0.81 -4 2 2 42.40 34.45 2.27 0.033 2.13 -3 1 10 0.64 27.47 2.27 0.029 0.79 0 7 4 26.02 35.97 2.25 0.033 1.03 8 2 1 77.63 98.64 2.24 0.055 1.21 8 3 5 26.27 0.82 2.23 0.005 0.87 11 4 1 36.94 9.59 2.22 0.017 0.85 Bond lengths and angles C2 - Distance Angles C3 1.3558 (0.0035) N1 1.3573 (0.0031) 120.47 (0.24) H2 0.9500 119.77 119.77 C2 - C3 N1 C3 - Distance Angles C2 1.3558 (0.0035) C4 1.4126 (0.0033) 118.79 (0.23) C7 1.4807 (0.0035) 120.28 (0.24) 120.91 (0.23) C3 - C2 C4 C4 - Distance Angles C5 1.3595 (0.0034) C3 1.4126 (0.0033) 119.90 (0.22) H4 0.9500 120.05 120.05 C4 - C5 C3 C5 - Distance Angles C4 1.3595 (0.0034) C6 1.4480 (0.0033) 122.51 (0.22) Cl5 1.7235 (0.0025) 121.88 (0.18) 115.61 (0.18) C5 - C4 C6 C6 - Distance Angles O6 1.2306 (0.0028) N1 1.3832 (0.0029) 121.21 (0.22) C5 1.4480 (0.0033) 125.65 (0.22) 113.14 (0.21) C6 - O6 N1 C7 - Distance Angles F7B 1.3326 (0.0030) F7A 1.3371 (0.0029) 106.45 (0.21) F7C 1.3461 (0.0029) 105.25 (0.22) 105.65 (0.21) C3 1.4807 (0.0035) 112.47 (0.20) 113.31 (0.23) 113.06 (0.21) C7 - F7B F7A F7C N1 - Distance Angles C2 1.3573 (0.0031) C6 1.3832 (0.0029) 125.18 (0.21) H1 0.8800 117.41 117.41 N1 - C2 C6 O6 - Distance Angles C6 1.2306 (0.0028) O6 - F7B - Distance Angles C7 1.3326 (0.0030) F7B - F7C - Distance Angles C7 1.3461 (0.0029) F7C - Cl5 - Distance Angles C5 1.7235 (0.0025) Cl5 - F7A - Distance Angles C7 1.3371 (0.0029) F7A - FMAP and GRID set by program FMAP 2 3 12 GRID -2.778 -2 -2 2.778 2 2 R1 = 0.0819 for 1630 unique reflections after merging for Fourier Electron density synthesis with coefficients Fo-Fc Highest peak 0.31 at 0.1872 0.9119 -0.0133 [ 0.06 A from CL5 ] Deepest hole -0.32 at 0.8354 0.6213 0.1424 [ 0.92 A from C2 ] Mean = 0.00, Rms deviation from mean = 0.08 e/A^3, Highest memory used = 1362 / 14256 Fourier peaks appended to .res file x y z sof U Peak Distances to nearest atoms (including symmetry equivalents) Q1 1 -0.0966 0.6385 -0.3730 1.00000 0.05 0.26 1.47 O6 1.63 H2 2.27 CL5 2.39 C2 Q2 1 0.3050 0.5331 0.0375 1.00000 0.05 0.25 0.76 C3 0.92 C4 1.63 H4 1.73 C2 Q3 1 0.2217 0.8117 -0.1781 1.00000 0.05 0.24 1.68 C5 1.69 CL5 2.10 H4 2.20 C4 Q4 1 0.2362 0.9007 -0.1379 1.00000 0.05 0.23 1.27 CL5 2.04 C5 2.34 H4 2.37 C4 Q5 1 0.0682 0.3434 0.0031 1.00000 0.05 0.23 1.51 C2 1.57 N1 1.63 H2 1.67 H1 Q6 1 0.0119 0.3841 -0.2738 1.00000 0.05 0.23 0.66 H1 1.51 N1 1.63 O6 2.41 C6 Q7 1 0.5535 0.4110 0.4751 1.00000 0.05 0.23 1.53 F7B 1.95 F7B 2.54 C7 2.56 H4 Q8 1 0.1809 0.7975 0.0184 1.00000 0.05 0.23 0.84 C5 0.97 CL5 1.88 C4 1.99 C6 Q9 1 0.0950 0.5648 -0.1074 1.00000 0.05 0.22 0.55 C6 0.88 N1 1.55 H1 1.64 O6 Q10 1 0.4169 0.6993 0.0925 1.00000 0.05 0.22 1.01 H4 1.53 C4 2.29 F7C 2.41 C5 Shortest distances between peaks (including symmetry equivalents) 3 4 0.82 3 8 1.72 4 8 1.73 2 10 1.85 7 10 1.92 7 7 2.00 1 5 2.08 6 9 2.10 5 9 2.12 5 6 2.18 5 9 2.26 8 9 2.31 2 9 2.34 4 7 2.37 1 6 2.46 1 6 2.50 1 4 2.54 3 8 2.54 3 6 2.56 2 8 2.60 3 9 2.63 6 8 2.64 4 6 2.64 8 10 2.64 1 9 2.70 3 7 2.75 5 6 2.78 3 10 2.84 1 5 2.90 2 4 2.90 4 10 2.93 2 3 2.93 5 8 2.93 2 3 2.94 2 5 3.00 Time profile in seconds ----------------------- 0.03: Read and process instructions 0.00: Fit rigid groups 0.00: Interpret restraints etc. 0.00: Generate connectivity array 0.02: Analyse DFIX/DANG restraints 0.00: Analyse SAME/SADI restraints 0.00: Generate CHIV restraints 0.00: Check if bonds in residues restrained 0.00: Generate DELU restraints 0.00: Generate SIMU restraints 0.00: Generate ISOR restraints 0.00: Generate NCSY restraints 0.00: Analyse other restraints etc. 0.47: Read intensity data, sort/merge etc. 0.00: Set up constraints 0.00: OSF, H-atoms from difference map 0.00: Set up l.s. refinement 0.00: Generate idealized H-atoms 0.19: Structure factors and derivatives 0.16: Sum l.s. matrices 0.00: Generate and apply antibumping restraints 0.02: Apply other restraints 0.03: Solve l.s. equations 0.00: Generate HTAB table 0.02: Other dependent quantities, CIF, tables 0.03: Analysis of variance 0.02: Merge reflections for Fourier and .fcf 0.02: Fourier summations 0.02: Peaksearch 0.00: Analyse peaklist +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + 2009src0246p21c finished at 13:05:42 Total CPU time: 1.0 secs + +++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++