++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ + SHELXTL XLMP CRYSTAL STRUCTURE REFINEMENT - MULTI-CPU VERSION + + Copyright(c) Bruker AXS Inc. 1993-2014 Version 2014/7 + + marc002 started at 11:48:47 on 27-Feb-2015 + ++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++++ Command line parameters: marc002 -a50000 -b3000 -c624 -t2 -a sets the approximate maximum number of atoms including hydrogens. -b sets the maximum number of full-matrix parameters (leave unchanged for CGLS). For example -b9000 allows refinement of 1000 anisotropic atoms or 3000 with BLOC 1. For a 32-bit version, -b times the square root of the number of threads should not exceed about 65500. -c sets the reflection buffer size. This depends on the CPU cache size but will rarely need changing. -t sets the number of threads, otherwise the multi-CPU version sets this equal to the number of available CPUs. For optimal performance on systems with hyperthreading, usually the hyperthreading should be switched off or -t used to halve the number of threads; e.g. -t4 rather than -t8 for an Intel i7 processor. Running 2 threads on 2 processors marc002.res created by SHELXL-2014/7 TITL marc002 in P2(1) CELL 1.54178 6.83490 7.36720 18.32550 90.0000 100.5931 90.0000 ZERR 2.00 0.00030 0.00030 0.00080 0.0000 0.0022 0.0000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H O Br UNIT 40 34 8 2 V = 907.04 F(000) = 408.0 Mu = 3.27 mm-1 Cell Wt = 802.49 Rho = 1.469 L.S. 10 BOND $H FMAP 2 PLAN 20 SIZE 0.086 0.371 0.453 TEMP -73.150 HTAB EQIV $1 -x+1, y+1/2, -z+1 HTAB O4 O3_$1 OMIT -2 -5 19 OMIT 0 1 14 OMIT -6 -6 5 OMIT -1 -1 2 OMIT 1 0 0 OMIT -1 1 2 OMIT 1 2 1 OMIT 1 0 4 OMIT 3 2 18 CONF ACTA WGHT 0.0749 0.0991 EXTI 0.009775 FVAR 0.31799 C1 1 0.653162 0.441435 0.372745 11.00000 0.02133 0.03057 = 0.03032 -0.00209 0.00666 0.00269 C2 1 0.632678 0.549004 0.442167 11.00000 0.02066 0.04177 = 0.02950 -0.00350 0.00402 0.00137 C3 1 0.771952 0.700696 0.448886 11.00000 0.02287 0.03820 = 0.03427 -0.00770 0.00133 0.00379 C4 1 0.875453 0.701196 0.394004 11.00000 0.02318 0.03232 = 0.03243 -0.00288 0.00171 0.00346 C5 1 0.805703 0.554793 0.337184 11.00000 0.01952 0.02998 = 0.03102 -0.00423 0.00597 -0.00090 AFIX 13 H5 2 0.921449 0.475467 0.332468 11.00000 -1.20000 AFIX 0 C6 1 0.450150 0.420831 0.323110 11.00000 0.02273 0.02921 = 0.03106 -0.00285 0.00606 -0.00021 C7 1 0.266236 0.324675 0.144785 11.00000 0.04250 0.05215 = 0.03658 -0.00584 0.00607 -0.00346 AFIX 43 H7 2 0.366411 0.397423 0.129670 11.00000 -1.20000 AFIX 0 C8 1 0.096994 0.272313 0.093654 11.00000 0.06208 0.06962 = 0.03969 -0.00968 -0.00562 -0.00083 AFIX 43 H8 2 0.081357 0.308831 0.043195 11.00000 -1.20000 AFIX 0 C9 1 -0.047167 0.166959 0.117281 11.00000 0.04811 0.05502 = 0.06966 -0.01620 -0.01094 -0.00607 AFIX 43 H9 2 -0.161552 0.130425 0.082734 11.00000 -1.20000 AFIX 0 C10 1 -0.026202 0.115231 0.189779 11.00000 0.03997 0.04443 = 0.06844 -0.00580 -0.00561 -0.01135 AFIX 43 H10 2 -0.126724 0.043797 0.205349 11.00000 -1.20000 AFIX 0 C11 1 0.140184 0.165817 0.240920 11.00000 0.04082 0.03610 = 0.04878 -0.00006 0.00195 -0.01012 AFIX 43 H11 2 0.155380 0.130546 0.291513 11.00000 -1.20000 AFIX 0 C12 1 0.283811 0.269494 0.215979 11.00000 0.02618 0.03190 = 0.03820 -0.00750 0.00275 -0.00012 C13 1 0.736147 0.252370 0.396335 11.00000 0.03125 0.03269 = 0.04364 0.00653 0.00375 0.00543 AFIX 137 H13A 2 0.644577 0.189418 0.423108 11.00000 -1.50000 H13B 2 0.866448 0.264817 0.428780 11.00000 -1.50000 H13C 2 0.750369 0.182229 0.352172 11.00000 -1.50000 AFIX 0 C14 1 1.042689 0.824836 0.386126 11.00000 0.03236 0.03991 = 0.04701 -0.00609 0.00830 -0.00823 AFIX 137 H14A 2 1.035058 0.934875 0.415519 11.00000 -1.50000 H14B 2 1.033430 0.857685 0.333781 11.00000 -1.50000 H14C 2 1.169631 0.763310 0.403893 11.00000 -1.50000 AFIX 0 C15 1 0.809846 0.596093 0.200665 11.00000 0.03161 0.03217 = 0.03430 -0.00372 0.00884 0.00340 AFIX 43 H15 2 0.921139 0.516647 0.206689 11.00000 -1.20000 AFIX 0 C16 1 0.735178 0.667204 0.131155 11.00000 0.03967 0.03730 = 0.03336 -0.00242 0.00805 -0.00202 AFIX 43 H16 2 0.794500 0.637233 0.089734 11.00000 -1.20000 AFIX 0 C17 1 0.573520 0.782095 0.123008 11.00000 0.04414 0.03302 = 0.03113 -0.00125 -0.00255 -0.00599 C18 1 0.486628 0.830098 0.182536 11.00000 0.03630 0.03352 = 0.04391 0.00222 0.00200 0.00511 AFIX 43 H18 2 0.374487 0.908602 0.175905 11.00000 -1.20000 AFIX 0 C19 1 0.565756 0.761862 0.251966 11.00000 0.03357 0.03606 = 0.03616 -0.00249 0.00829 0.00647 AFIX 43 H19 2 0.511370 0.798973 0.293704 11.00000 -1.20000 AFIX 0 C20 1 0.724588 0.639068 0.261797 11.00000 0.02447 0.02877 = 0.03232 -0.00041 0.00403 0.00106 O1 3 0.298011 0.489643 0.333351 11.00000 0.02216 0.05736 = 0.05106 -0.01600 0.00421 0.00598 O2 3 0.462119 0.310681 0.265621 11.00000 0.02345 0.04083 = 0.03566 -0.01017 0.00331 0.00158 O3 3 0.528549 0.508089 0.487150 11.00000 0.03710 0.06252 = 0.03400 -0.00614 0.01388 -0.00762 O4 3 0.804814 0.813999 0.508821 11.00000 0.02767 0.05995 = 0.04185 -0.02308 0.00332 0.00122 REM AFIX 83 H4 2 0.707101 0.853226 0.516774 11.00000 -1.50000 REM AFIX 0 BR1 4 0.466382 0.880881 0.028174 11.00000 0.07483 0.04642 = 0.03622 0.00564 -0.00796 0.00458 HKLF 4 Covalent radii and connectivity table for marc002 in P2(1) C 0.770 H 0.320 O 0.660 BR 1.140 C1 - C6 C2 C13 C5 C2 - O3 C3 C1 C3 - C4 O4 C2 C4 - C3 C14 C5 C5 - C4 C20 C1 C6 - O1 O2 C1 C7 - C12 C8 C8 - C9 C7 C9 - C10 C8 C10 - C9 C11 C11 - C10 C12 C12 - C7 C11 O2 C13 - C1 C14 - C4 C15 - C16 C20 C16 - C17 C15 C17 - C16 C18 Br1 C18 - C17 C19 C19 - C18 C20 C20 - C15 C19 C5 O1 - C6 O2 - C6 C12 O3 - C2 O4 - C3 Br1 - C17 Operators for generating equivalent atoms: $1 -x+1, y+1/2, -z+1 Floating origin restraints generated 19617 Reflections read, of which 57 rejected -8 =< h =< 8, -9 =< k =< 9, -22 =< l =< 22, Max. 2-theta = 149.56 0 Systematic absence violations 0 Inconsistent equivalents 3698 Unique reflections, of which 0 suppressed R(int) = 0.0685 R(sigma) = 0.0490 Friedel opposites not merged Maximum memory for data reduction = 2827 / 36886 Number of data for d > 0.799A (CIF: max) and d > 0.833A (CIF: full) (ignoring systematic absences): Unique reflections found (point group) 3698 3265 Unique reflections possible (point group) 3737 3279 Unique reflections found (Laue group) 2011 1774 Unique reflections possible (Laue group) 2019 1777 Unique Friedel pairs found 1687 1491 Unique Friedel pairs possible 1718 1502 Default effective X-H and X-D distances for T = -73.2C 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 = 623 Memory required = 3434 / 344599 wR2 = 0.1213 before cycle 1 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31797 0.00137 -0.015 OSF 2 0.00976 0.00154 -0.007 EXTI Mean shift/esd = 0.003 Maximum = -0.017 for U22 Br1 Max. shift = 0.000 A for H4 Max. dU = 0.000 for C10 Least-squares cycle 2 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 2 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 -0.004 OSF 2 0.00976 0.00154 -0.002 EXTI Mean shift/esd = 0.001 Maximum = -0.006 for U22 Br1 Max. shift = 0.000 A for H14A Max. dU = 0.000 for C10 Least-squares cycle 3 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 3 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 0.000 OSF 2 0.00976 0.00154 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.002 for tors H14A Max. shift = 0.000 A for H14C Max. dU = 0.000 for C8 Least-squares cycle 4 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 4 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 0.000 OSF 2 0.00976 0.00154 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.001 for tors H14A Max. shift = 0.000 A for H14C Max. dU = 0.000 for C10 Least-squares cycle 5 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 5 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 0.000 OSF 2 0.00976 0.00154 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.001 for tors H14A Max. shift = 0.000 A for H14A Max. dU = 0.000 for C8 Least-squares cycle 6 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 6 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 0.000 OSF 2 0.00976 0.00154 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for tors H14A Max. shift = 0.000 A for H14A Max. dU = 0.000 for O3 Least-squares cycle 7 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 7 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 0.000 OSF 2 0.00976 0.00154 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for tors H14A Max. shift = 0.000 A for H14C Max. dU = 0.000 for C14 Least-squares cycle 8 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 8 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 0.000 OSF 2 0.00976 0.00154 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for x Br1 Max. shift = 0.000 A for H14C Max. dU = 0.000 for C7 Least-squares cycle 9 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 9 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 0.000 OSF 2 0.00976 0.00154 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for x Br1 Max. shift = 0.000 A for H14C Max. dU = 0.000 for C18 Least-squares cycle 10 Maximum vector length = 623 Memory required = 3434 / 344599 wR2 = 0.1214 before cycle 10 for 3698 data and 232 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 N value esd shift/esd parameter 1 0.31796 0.00137 0.000 OSF 2 0.00976 0.00154 0.000 EXTI Mean shift/esd = 0.000 Maximum = 0.000 for OSF Max. shift = 0.000 A for H4 Max. dU = 0.000 for C8 Largest correlation matrix elements 0.651 EXTI / OSF 0.619 U33 Br1 / OSF 0.629 U22 Br1 / OSF 0.569 U11 Br1 / OSF Idealized hydrogen atom generation before cycle 11 Name x y z AFIX d(X-H) shift Bonded to Conformation determined by H5 0.9214 0.4755 0.3325 13 1.000 0.000 C5 C4 C20 C1 H7 0.3664 0.3974 0.1297 43 0.950 0.000 C7 C12 C8 H8 0.0813 0.3088 0.0432 43 0.950 0.000 C8 C9 C7 H9 -0.1615 0.1304 0.0827 43 0.950 0.000 C9 C10 C8 H10 -0.1267 0.0438 0.2053 43 0.950 0.000 C10 C9 C11 H11 0.1554 0.1306 0.2915 43 0.950 0.000 C11 C10 C12 H13A 0.6446 0.1894 0.4231 137 0.980 0.000 C13 C1 H13A H13B 0.8665 0.2648 0.4288 137 0.980 0.000 C13 C1 H13A H13C 0.7504 0.1822 0.3522 137 0.980 0.000 C13 C1 H13A H14A 1.0351 0.9348 0.4156 137 0.980 0.000 C14 C4 H14A H14B 1.0334 0.8578 0.3338 137 0.980 0.000 C14 C4 H14A H14C 1.1696 0.7633 0.4039 137 0.980 0.000 C14 C4 H14A H15 0.9211 0.5166 0.2067 43 0.950 0.000 C15 C16 C20 H16 0.7945 0.6372 0.0897 43 0.950 0.000 C16 C17 C15 H18 0.3745 0.9086 0.1759 43 0.950 0.000 C18 C17 C19 H19 0.5114 0.7990 0.2937 43 0.950 0.000 C19 C18 C20 marc002 in P2(1) ATOM x y z sof U11 U22 U33 U23 U13 U12 Ueq C1 0.65316 0.44143 0.37275 1.00000 0.02134 0.03056 0.03030 -0.00209 0.00666 0.00269 0.02716 0.00832 0.00058 0.00058 0.00024 0.00000 0.00167 0.00198 0.00215 0.00160 0.00151 0.00149 0.00084 C2 0.63268 0.54901 0.44217 1.00000 0.02065 0.04176 0.02951 -0.00350 0.00402 0.00136 0.03072 0.00868 0.00060 0.00067 0.00026 0.00000 0.00170 0.00236 0.00226 0.00182 0.00150 0.00168 0.00091 C3 0.77195 0.70069 0.44888 1.00000 0.02286 0.03820 0.03426 -0.00770 0.00132 0.00378 0.03227 0.00851 0.00061 0.00069 0.00026 0.00000 0.00175 0.00230 0.00236 0.00184 0.00152 0.00169 0.00092 C4 0.87545 0.70120 0.39401 1.00000 0.02317 0.03231 0.03242 -0.00288 0.00171 0.00347 0.02973 0.00812 0.00058 0.00061 0.00025 0.00000 0.00178 0.00209 0.00229 0.00174 0.00151 0.00166 0.00088 C5 0.80570 0.55479 0.33719 1.00000 0.01950 0.02999 0.03102 -0.00422 0.00597 -0.00089 0.02667 0.00802 0.00057 0.00058 0.00025 0.00000 0.00163 0.00195 0.00218 0.00161 0.00145 0.00146 0.00083 H5 0.92145 0.47547 0.33247 1.00000 0.03200 0.00000 0.00000 C6 0.45014 0.42083 0.32311 1.00000 0.02274 0.02920 0.03106 -0.00284 0.00607 -0.00021 0.02752 0.00783 0.00058 0.00054 0.00024 0.00000 0.00173 0.00222 0.00204 0.00151 0.00146 0.00144 0.00087 C7 0.26624 0.32467 0.14479 1.00000 0.04248 0.05214 0.03656 -0.00584 0.00607 -0.00346 0.04388 0.01022 0.00080 0.00080 0.00030 0.00000 0.00259 0.00303 0.00261 0.00212 0.00194 0.00217 0.00117 H7 0.36642 0.39741 0.12967 1.00000 0.05266 0.00000 0.00000 C8 0.09698 0.27231 0.09365 1.00000 0.06205 0.06961 0.03970 -0.00966 -0.00564 -0.00080 0.05902 0.01213 0.00104 0.00107 0.00036 0.00000 0.00360 0.00422 0.00315 0.00286 0.00258 0.00303 0.00159 H8 0.08133 0.30884 0.04319 1.00000 0.07083 0.00000 0.00000 C9 -0.04716 0.16696 0.11728 1.00000 0.04810 0.05503 0.06964 -0.01620 -0.01093 -0.00609 0.06035 0.01150 0.00096 0.00094 0.00042 0.00000 0.00314 0.00358 0.00446 0.00326 0.00274 0.00278 0.00167 H9 -0.16154 0.13042 0.08273 1.00000 0.07242 0.00000 0.00000 C10 -0.02620 0.11523 0.18977 1.00000 0.03997 0.04443 0.06840 -0.00580 -0.00561 -0.01134 0.05291 0.01111 0.00087 0.00084 0.00040 0.00000 0.00278 0.00296 0.00410 0.00271 0.00247 0.00235 0.00143 H10 -0.12672 0.04379 0.20534 1.00000 0.06349 0.00000 0.00000 C11 0.14018 0.16582 0.24092 1.00000 0.04081 0.03609 0.04880 -0.00006 0.00194 -0.01012 0.04270 0.00998 0.00079 0.00072 0.00033 0.00000 0.00251 0.00242 0.00304 0.00217 0.00210 0.00208 0.00112 H11 0.15537 0.13056 0.29151 1.00000 0.05123 0.00000 0.00000 C12 0.28381 0.26949 0.21598 1.00000 0.02616 0.03189 0.03820 -0.00750 0.00274 -0.00011 0.03249 0.00834 0.00063 0.00062 0.00027 0.00000 0.00193 0.00216 0.00245 0.00176 0.00168 0.00164 0.00093 C13 0.73615 0.25237 0.39634 1.00000 0.03125 0.03268 0.04363 0.00652 0.00373 0.00543 0.03625 0.00972 0.00069 0.00066 0.00030 0.00000 0.00212 0.00225 0.00273 0.00196 0.00184 0.00181 0.00100 H13A 0.64458 0.18942 0.42311 1.00000 0.05438 0.00000 0.00000 H13B 0.86645 0.26482 0.42878 1.00000 0.05438 0.00000 0.00000 H13C 0.75038 0.18223 0.35217 1.00000 0.05438 0.00000 0.00000 C14 1.04269 0.82484 0.38613 1.00000 0.03234 0.03991 0.04701 -0.00610 0.00830 -0.00823 0.03963 0.00925 0.00069 0.00071 0.00030 0.00000 0.00226 0.00246 0.00289 0.00201 0.00193 0.00192 0.00111 H14A 1.03511 0.93483 0.41555 1.00000 0.05944 0.00000 0.00000 H14B 1.03337 0.85776 0.33379 1.00000 0.05944 0.00000 0.00000 H14C 1.16963 0.76328 0.40386 1.00000 0.05944 0.00000 0.00000 C15 0.80984 0.59609 0.20067 1.00000 0.03159 0.03216 0.03431 -0.00371 0.00882 0.00340 0.03234 0.00920 0.00068 0.00065 0.00027 0.00000 0.00206 0.00206 0.00242 0.00181 0.00174 0.00173 0.00092 H15 0.92114 0.51665 0.20669 1.00000 0.03881 0.00000 0.00000 C16 0.73518 0.66720 0.13116 1.00000 0.03965 0.03729 0.03336 -0.00243 0.00805 -0.00201 0.03660 0.00933 0.00073 0.00068 0.00028 0.00000 0.00234 0.00234 0.00244 0.00188 0.00183 0.00198 0.00098 H16 0.79450 0.63723 0.08973 1.00000 0.04391 0.00000 0.00000 C17 0.57353 0.78210 0.12301 1.00000 0.04416 0.03301 0.03112 -0.00126 -0.00254 -0.00600 0.03730 0.00887 0.00076 0.00066 0.00027 0.00000 0.00252 0.00235 0.00240 0.00188 0.00182 0.00194 0.00101 C18 0.48662 0.83010 0.18254 1.00000 0.03629 0.03351 0.04391 0.00222 0.00200 0.00511 0.03858 0.01003 0.00076 0.00066 0.00030 0.00000 0.00230 0.00245 0.00278 0.00184 0.00186 0.00174 0.00107 H18 0.37448 0.90860 0.17590 1.00000 0.04630 0.00000 0.00000 C19 0.56576 0.76186 0.25197 1.00000 0.03356 0.03605 0.03616 -0.00250 0.00829 0.00646 0.03502 0.00943 0.00070 0.00065 0.00028 0.00000 0.00211 0.00233 0.00249 0.00183 0.00177 0.00184 0.00098 H19 0.51137 0.79897 0.29371 1.00000 0.04202 0.00000 0.00000 C20 0.72459 0.63907 0.26180 1.00000 0.02446 0.02877 0.03231 -0.00041 0.00403 0.00106 0.02867 0.00832 0.00061 0.00058 0.00026 0.00000 0.00186 0.00200 0.00227 0.00167 0.00156 0.00157 0.00086 O1 0.29801 0.48964 0.33335 1.00000 0.02216 0.05735 0.05105 -0.01601 0.00420 0.00598 0.04384 0.00684 0.00047 0.00057 0.00022 0.00000 0.00144 0.00225 0.00217 0.00177 0.00134 0.00148 0.00088 O2 0.46212 0.31068 0.26562 1.00000 0.02344 0.04083 0.03565 -0.01018 0.00331 0.00159 0.03357 0.00595 0.00043 0.00048 0.00018 0.00000 0.00136 0.00159 0.00180 0.00140 0.00119 0.00126 0.00070 O3 0.52855 0.50809 0.48715 1.00000 0.03709 0.06252 0.03400 -0.00614 0.01388 -0.00762 0.04360 0.00737 0.00051 0.00064 0.00021 0.00000 0.00172 0.00238 0.00182 0.00172 0.00136 0.00161 0.00087 O4 0.80482 0.81400 0.50882 1.00000 0.02767 0.05993 0.04185 -0.02309 0.00333 0.00122 0.04354 0.00661 0.00051 0.00058 0.00021 0.00000 0.00151 0.00217 0.00195 0.00167 0.00129 0.00154 0.00087 H4 0.70713 0.85316 0.51678 1.00000 0.06531 0.14933 0.01172 0.01190 0.00417 0.00000 0.00000 Br1 0.46638 0.88088 0.02817 1.00000 0.07483 0.04641 0.03622 0.00564 -0.00796 0.00458 0.05479 0.00111 0.00010 0.00009 0.00003 0.00000 0.00044 0.00034 0.00031 0.00025 0.00022 0.00030 0.00026 Final Structure Factor Calculation for marc002 in P2(1) Total number of l.s. parameters = 232 Maximum vector length = 623 Memory required = 3204 / 30534 wR2 = 0.1214 before cycle 11 for 3698 data and 2 / 232 parameters GooF = S = 1.114; Restrained GooF = 1.114 for 1 restraints Weight = 1 / [ sigma^2(Fo^2) + ( 0.0749 * P )^2 + 0.10 * P ] where P = ( Max ( Fo^2, 0 ) + 2 * Fc^2 ) / 3 R1 = 0.0441 for 3523 Fo > 4sig(Fo) and 0.0455 for all 3698 data wR2 = 0.1214, GooF = S = 1.114, Restrained GooF = 1.114 for all data Flack x = -0.025(31) by classical fit to all intensities -0.014(26) from 1495 selected quotients (Parsons' method) Occupancy sum of asymmetric unit = 25.00 for non-hydrogen and 17.00 for H and D atoms Principal mean square atomic displacements U 0.0328 0.0293 0.0195 C1 0.0429 0.0287 0.0205 C2 0.0466 0.0284 0.0219 C3 0.0379 0.0295 0.0218 C4 0.0348 0.0263 0.0190 C5 0.0331 0.0272 0.0223 C6 0.0545 0.0428 0.0344 C7 0.0767 0.0679 0.0325 C8 0.0916 0.0584 0.0310 C9 0.0788 0.0527 0.0272 C10 0.0558 0.0444 0.0279 C11 0.0443 0.0279 0.0252 C12 0.0470 0.0367 0.0250 C13 0.0512 0.0406 0.0271 C14 0.0372 0.0348 0.0251 C15 0.0412 0.0366 0.0320 C16 0.0525 0.0336 0.0258 C17 0.0479 0.0391 0.0287 C18 0.0418 0.0368 0.0264 C19 0.0329 0.0289 0.0242 C20 0.0727 0.0380 0.0208 O1 0.0496 0.0278 0.0233 O2 0.0659 0.0385 0.0264 O3 0.0767 0.0279 0.0259 O4 0.0863 0.0488 0.0294 Br1 0 atoms may be split and 0 atoms NPD Analysis of variance for reflections employed in refinement K = Mean[Fo^2] / Mean[Fc^2] for group Fc/Fc(max) 0.000 0.030 0.045 0.059 0.072 0.088 0.108 0.132 0.173 0.250 1.000 Number in group 382. 358. 387. 355. 371. 369. 367. 367. 373. 369. GooF 0.861 1.151 1.389 1.375 1.206 0.977 0.968 1.056 1.050 0.984 K 1.010 1.006 1.008 1.032 1.019 1.018 1.001 0.996 1.000 1.012 Resolution(A) 0.80 0.83 0.86 0.90 0.95 1.01 1.08 1.20 1.37 1.71 inf Number in group 372. 373. 374. 370. 359. 373. 368. 372. 366. 371. GooF 1.492 1.203 1.133 0.995 0.977 0.950 0.968 0.956 1.094 1.242 K 0.950 1.006 1.015 1.020 1.015 1.015 1.014 1.004 1.007 1.009 R1 0.111 0.074 0.064 0.049 0.045 0.041 0.040 0.037 0.038 0.038 Recommended weighting scheme: WGHT 0.0749 0.1020 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). Error/esd is calculated as sqrt(wD^2/) where w is given by the weight formula, D = Fo^2-Fc^2 and <> refers to the average over all reflections. h k l Fo^2 Fc^2 Error/esd Fc/Fc(max) Resolution(A) 4 3 15 109.68 222.59 4.90 0.136 0.85 4 1 17 36.69 91.10 4.81 0.087 0.82 2 -5 17 8.77 26.46 4.81 0.047 0.80 -5 6 12 15.85 35.21 4.35 0.054 0.82 -1 -9 3 7.49 24.02 4.34 0.045 0.81 5 3 14 24.87 55.57 4.33 0.068 0.81 -6 1 6 214.42 384.77 4.30 0.179 1.11 -2 6 17 19.42 61.23 4.25 0.071 0.81 -4 -7 12 3.75 13.41 4.23 0.033 0.80 -5 -3 19 9.19 30.64 4.16 0.050 0.80 2 1 5 56.14 32.89 4.13 0.052 2.16 -7 -4 9 15.69 33.53 4.09 0.053 0.83 -2 -4 19 22.38 53.17 3.95 0.066 0.85 -1 9 3 13.45 27.34 3.87 0.048 0.81 -1 9 1 22.12 37.75 3.77 0.056 0.81 3 3 17 59.32 116.51 3.64 0.098 0.84 -1 -8 11 52.17 87.83 3.63 0.085 0.81 1 9 2 16.83 32.33 3.58 0.052 0.81 -5 6 7 26.17 47.12 3.53 0.063 0.89 -6 5 7 21.80 43.26 3.49 0.060 0.88 2 -1 5 51.27 32.00 3.48 0.052 2.16 -1 8 10 16.25 28.18 3.46 0.048 0.82 5 3 3 42.01 92.47 3.43 0.088 1.12 0 -1 16 62.77 145.30 3.40 0.110 1.11 -5 6 8 25.52 52.88 3.38 0.066 0.88 6 -4 9 21.05 38.76 3.37 0.057 0.81 -4 0 16 64.83 39.47 3.36 0.057 1.03 -1 0 7 13.71 23.15 3.36 0.044 2.57 -3 6 16 22.37 39.82 3.31 0.057 0.81 6 -4 0 19.70 50.58 3.19 0.065 0.96 1 -4 14 97.64 68.91 3.08 0.076 1.02 -1 9 2 14.82 26.80 3.07 0.047 0.81 -1 8 11 57.44 91.20 3.05 0.087 0.81 3 2 16 45.78 96.63 3.05 0.090 0.91 5 -6 5 40.33 81.02 3.05 0.082 0.85 -5 2 14 97.26 55.72 3.05 0.068 0.99 5 -2 15 37.97 66.69 2.99 0.074 0.80 2 8 0 35.87 59.77 2.98 0.070 0.89 0 -2 20 165.77 254.07 2.91 0.145 0.87 1 -5 0 254.85 194.61 2.90 0.127 1.44 -1 -5 1 279.95 214.29 2.89 0.133 1.44 0 8 5 51.33 78.02 2.84 0.080 0.89 -6 2 16 33.24 19.50 2.80 0.040 0.85 5 -2 2 51.01 81.00 2.78 0.082 1.22 -2 -3 1 1891.06 1484.48 2.78 0.351 1.99 5 6 4 79.30 52.18 2.76 0.066 0.87 1 -3 0 140.99 109.44 2.76 0.095 2.31 -6 0 13 19.14 11.37 2.75 0.031 0.96 -1 1 9 433.26 559.35 2.74 0.215 1.95 4 -8 0 54.42 37.24 2.71 0.056 0.81 Bond lengths and angles C1 - Distance Angles C6 1.5204 (0.0058) C2 1.5270 (0.0058) 109.69 (0.31) C13 1.5358 (0.0064) 109.09 (0.36) 108.78 (0.39) C5 1.5681 (0.0052) 114.08 (0.36) 103.86 (0.34) 111.14 (0.32) C1 - C6 C2 C13 C2 - Distance Angles O3 1.2217 (0.0053) C3 1.4584 (0.0066) 125.75 (0.45) C1 1.5270 (0.0058) 126.02 (0.45) 108.04 (0.34) C2 - O3 C3 C3 - Distance Angles C4 1.3317 (0.0062) O4 1.3649 (0.0057) 125.05 (0.44) C2 1.4584 (0.0066) 111.56 (0.41) 123.02 (0.41) C3 - C4 O4 C4 - Distance Angles C3 1.3317 (0.0062) C14 1.4892 (0.0062) 126.77 (0.44) C5 1.5141 (0.0061) 111.93 (0.38) 121.29 (0.37) C4 - C3 C14 C5 - Distance Angles C4 1.5141 (0.0061) C20 1.5231 (0.0063) 110.46 (0.35) C1 1.5681 (0.0052) 104.06 (0.33) 115.79 (0.35) H5 1.0000 108.76 108.76 108.76 C5 - C4 C20 C1 C6 - Distance Angles O1 1.2021 (0.0052) O2 1.3442 (0.0050) 123.78 (0.40) C1 1.5204 (0.0058) 125.80 (0.39) 110.41 (0.31) C6 - O1 O2 C7 - Distance Angles C12 1.3506 (0.0073) C8 1.4024 (0.0080) 118.60 (0.54) H7 0.9500 120.70 120.70 C7 - C12 C8 C8 - Distance Angles C9 1.3847 (0.0106) C7 1.4024 (0.0080) 119.48 (0.63) H8 0.9500 120.26 120.26 C8 - C9 C7 C9 - Distance Angles C10 1.3640 (0.0104) C8 1.3847 (0.0106) 120.52 (0.57) H9 0.9500 119.74 119.74 C9 - C10 C8 C10 - Distance Angles C9 1.3640 (0.0104) C11 1.3852 (0.0079) 120.66 (0.57) H10 0.9500 119.67 119.67 C10 - C9 C11 C11 - Distance Angles C10 1.3852 (0.0079) C12 1.3860 (0.0068) 117.92 (0.55) H11 0.9500 121.04 121.04 C11 - C10 C12 C12 - Distance Angles C7 1.3506 (0.0073) C11 1.3860 (0.0068) 122.81 (0.47) O2 1.4133 (0.0053) 118.05 (0.41) 119.03 (0.46) C12 - C7 C11 C13 - Distance Angles C1 1.5358 (0.0064) H13A 0.9800 109.47 H13B 0.9800 109.47 109.47 H13C 0.9800 109.47 109.47 109.47 C13 - C1 H13A H13B C14 - Distance Angles C4 1.4892 (0.0062) H14A 0.9800 109.47 H14B 0.9800 109.47 109.47 H14C 0.9800 109.47 109.47 109.47 C14 - C4 H14A H14B C15 - Distance Angles C16 1.3851 (0.0072) C20 1.3910 (0.0062) 121.10 (0.43) H15 0.9500 119.45 119.45 C15 - C16 C20 C16 - Distance Angles C17 1.3780 (0.0073) C15 1.3851 (0.0072) 118.98 (0.43) H16 0.9500 120.51 120.51 C16 - C17 C15 C17 - Distance Angles C16 1.3780 (0.0073) C18 1.3806 (0.0070) 121.64 (0.47) Br1 1.9022 (0.0050) 120.02 (0.38) 118.33 (0.39) C17 - C16 C18 C18 - Distance Angles C17 1.3806 (0.0070) C19 1.3824 (0.0072) 118.80 (0.45) H18 0.9500 120.60 120.60 C18 - C17 C19 C19 - Distance Angles C18 1.3824 (0.0071) C20 1.3991 (0.0061) 121.11 (0.43) H19 0.9500 119.45 119.45 C19 - C18 C20 C20 - Distance Angles C15 1.3910 (0.0062) C19 1.3991 (0.0061) 118.26 (0.44) C5 1.5231 (0.0063) 120.08 (0.38) 121.65 (0.38) C20 - C15 C19 O1 - Distance Angles C6 1.2021 (0.0052) O1 - O2 - Distance Angles C6 1.3442 (0.0050) C12 1.4133 (0.0053) 117.68 (0.31) O2 - C6 O3 - Distance Angles C2 1.2217 (0.0053) O3 - O4 - Distance Angles C3 1.3649 (0.0057) H4 0.7656 (0.0783) 111.32 (6.08) O4 - C3 Br1 - Distance Angles C17 1.9022 (0.0050) Br1 - Selected torsion angles 58.33 ( 0.62) C6 - C1 - C2 - O3 -60.92 ( 0.60) C13 - C1 - C2 - O3 -179.36 ( 0.47) C5 - C1 - C2 - O3 -126.49 ( 0.38) C6 - C1 - C2 - C3 114.26 ( 0.40) C13 - C1 - C2 - C3 -4.17 ( 0.47) C5 - C1 - C2 - C3 174.85 ( 0.49) O3 - C2 - C3 - C4 -0.35 ( 0.54) C1 - C2 - C3 - C4 1.55 ( 0.78) O3 - C2 - C3 - O4 -173.65 ( 0.40) C1 - C2 - C3 - O4 -1.10 ( 0.79) O4 - C3 - C4 - C14 -174.24 ( 0.45) C2 - C3 - C4 - C14 178.23 ( 0.43) O4 - C3 - C4 - C5 5.09 ( 0.55) C2 - C3 - C4 - C5 117.42 ( 0.40) C3 - C4 - C5 - C20 -63.21 ( 0.50) C14 - C4 - C5 - C20 -7.48 ( 0.50) C3 - C4 - C5 - C1 171.89 ( 0.40) C14 - C4 - C5 - C1 126.02 ( 0.36) C6 - C1 - C5 - C4 6.66 ( 0.43) C2 - C1 - C5 - C4 -110.14 ( 0.40) C13 - C1 - C5 - C4 4.61 ( 0.49) C6 - C1 - C5 - C20 -114.76 ( 0.40) C2 - C1 - C5 - C20 128.45 ( 0.40) C13 - C1 - C5 - C20 5.30 ( 0.61) C2 - C1 - C6 - O1 124.35 ( 0.49) C13 - C1 - C6 - O1 -110.71 ( 0.49) C5 - C1 - C6 - O1 -173.61 ( 0.35) C2 - C1 - C6 - O2 -54.56 ( 0.44) C13 - C1 - C6 - O2 70.37 ( 0.44) C5 - C1 - C6 - O2 0.30 ( 0.95) C12 - C7 - C8 - C9 0.49 ( 1.05) C7 - C8 - C9 - C10 -0.52 ( 1.05) C8 - C9 - C10 - C11 -0.22 ( 0.93) C9 - C10 - C11 - C12 -1.08 ( 0.83) C8 - C7 - C12 - C11 175.01 ( 0.51) C8 - C7 - C12 - O2 1.05 ( 0.82) C10 - C11 - C12 - C7 -175.00 ( 0.47) C10 - C11 - C12 - O2 -0.09 ( 0.74) C20 - C15 - C16 - C17 1.06 ( 0.75) C15 - C16 - C17 - C18 -179.62 ( 0.37) C15 - C16 - C17 - Br1 0.57 ( 0.76) C16 - C17 - C18 - C19 -178.76 ( 0.38) Br1 - C17 - C18 - C19 -3.21 ( 0.75) C17 - C18 - C19 - C20 -2.43 ( 0.70) C16 - C15 - C20 - C19 178.23 ( 0.42) C16 - C15 - C20 - C5 4.12 ( 0.71) C18 - C19 - C20 - C15 -176.56 ( 0.43) C18 - C19 - C20 - C5 120.81 ( 0.43) C4 - C5 - C20 - C15 -121.27 ( 0.43) C1 - C5 - C20 - C15 -58.50 ( 0.51) C4 - C5 - C20 - C19 59.42 ( 0.55) C1 - C5 - C20 - C19 -2.12 ( 0.65) O1 - C6 - O2 - C12 176.82 ( 0.37) C1 - C6 - O2 - C12 116.57 ( 0.49) C7 - C12 - O2 - C6 -67.20 ( 0.56) C11 - C12 - O2 - C6 Specified hydrogen bonds (with esds except fixed and riding H) D-H H...A D...A <(DHA) 0.77(8) 1.96(8) 2.703(5) 162(8) O4-H4...O3_$1 Hydrogen bonds with H..A < r(A) + 2.000 Angstroms and 110 deg. Appropriate HTAB instructions appended to .res file for future use. D-H d(D-H) d(H..A)