#------------------------------------------------------------------------------ #$Date: 2021-10-29 02:37:40 +0300 (Fri, 29 Oct 2021) $ #$Revision: 270120 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/86/7708614.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7708614 loop_ _publ_author_name 'Horsley Downie, Thomas Mardale' 'Charman, Rex S. C.' 'Hall, Jonathan W.' 'Mahon, Mary F.' 'Lowe, John P.' 'Liptrot, David Jonathan' _publ_section_title ; A Stable Ring-Expanded NHC-Supported Copper Boryl and its Reactivity towards Heterocumulenes ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D1DT03540A _journal_year 2021 _chemical_formula_moiety 'C46 H66 B Cu N4 O3' _chemical_formula_sum 'C46 H66 B Cu N4 O3' _chemical_formula_weight 797.37 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-04-22 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-10-19 deposited with the CCDC. 2021-10-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 16.4325(2) _cell_length_b 21.3202(4) _cell_length_c 25.9216(5) _cell_measurement_reflns_used 12777 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 28.6360 _cell_measurement_theta_min 3.1140 _cell_volume 9081.5(3) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.1468 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.978 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'New Xcalibur, EosS2' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0621 _diffrn_reflns_av_unetI/netI 0.0518 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.978 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 78752 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.978 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.130 _diffrn_reflns_theta_min 2.935 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.523 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.87044 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.166 _exptl_crystal_description block _exptl_crystal_F_000 3424 _exptl_crystal_size_max 0.401 _exptl_crystal_size_mid 0.282 _exptl_crystal_size_min 0.162 _refine_diff_density_max 0.719 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 623 _refine_ls_number_reflns 11957 _refine_ls_number_restraints 293 _refine_ls_restrained_S_all 1.047 _refine_ls_R_factor_all 0.0996 _refine_ls_R_factor_gt 0.0512 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+7.7073P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1032 _refine_ls_wR_factor_ref 0.1241 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7591 _reflns_number_total 11957 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL e20djl04 CELL 0.71073 16.4325 21.3202 25.9216 90 90 90 ZERR 8 0.0002 0.0004 0.0005 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H B Cu N O UNIT 368 528 8 8 32 24 SADI 0.005 N1 C5 N1 C5A SADI 0.005 C6 C5 C7 C6 C8 C7 C9 C8 C9 C10 C5 C10 C6A C5A C7A C6A C8A C7A = C9A C8A C9A C10A C5A C10A SADI 0.005 C6 C11 C6A C11A C14A C10A C14 C10 SADI 0.005 C13 C11 C13A C11A C12A C11A C12 C11 C16A C14A C16 C14 C15A C14A = C15 C14 SIMU 0.02 0.01 2 C10A C10 C9A C9 C8A C8 C7A C6A C5A C5 C6 SIMU 0.02 0.01 2 C14A C14 C11A C11 SIMU 0.02 0.01 2 C15A C15 C16A C16 C13A C13 C12 C12A L.S. 10 PLAN 3 BOND LIST 6 fmap 2 TEMP -123 acta SHEL 999 0.73 OMIT 6 0 2 REM REM REM WGHT 0.038900 7.707300 FVAR 0.16403 CU1 4 0.638180 0.268328 0.412047 11.00000 0.02367 0.02830 = 0.01685 -0.00094 0.00039 0.00397 O1 6 0.595055 0.248045 0.612215 11.00000 0.10583 0.03598 = 0.02345 0.00138 0.01829 -0.01928 O2 6 0.600208 0.405210 0.489661 11.00000 0.03263 0.02691 = 0.03321 0.00367 0.00329 0.00678 O3 6 0.733935 0.377478 0.508287 11.00000 0.02917 0.02368 = 0.03262 0.00352 0.00365 0.00041 N1 5 0.558376 0.217609 0.323899 11.00000 0.02293 0.04072 = 0.02103 -0.00451 -0.00056 0.00130 N2 5 0.682737 0.257502 0.302525 11.00000 0.02759 0.03913 = 0.01966 -0.00170 0.00346 0.00218 N3 5 0.626084 0.246363 0.523053 11.00000 0.02892 0.02255 = 0.02156 -0.00343 -0.00019 -0.00087 N4 5 0.628924 0.337567 0.568248 11.00000 0.03756 0.02334 = 0.01862 -0.00314 0.00525 -0.00178 C1 1 0.626788 0.247518 0.338962 11.00000 0.02477 0.02534 = 0.01917 -0.00083 0.00058 0.00785 C2 1 0.536750 0.201801 0.270065 11.00000 0.04067 0.07278 = 0.02806 -0.01644 -0.00387 -0.00668 AFIX 23 H2A 2 0.542562 0.156949 0.264980 11.00000 -1.20000 H2B 2 0.480240 0.212666 0.263972 11.00000 -1.20000 AFIX 0 C3 1 0.588252 0.235024 0.232710 11.00000 0.05426 0.10043 = 0.02568 -0.01013 -0.00203 -0.00849 AFIX 23 H3A 2 0.570817 0.278371 0.230051 11.00000 -1.20000 H3B 2 0.582736 0.215766 0.198988 11.00000 -1.20000 AFIX 0 C4 1 0.675673 0.232572 0.249533 11.00000 0.04211 0.05971 = 0.02240 -0.00752 0.00286 0.00086 AFIX 23 H4A 2 0.695017 0.189604 0.248544 11.00000 -1.20000 H4B 2 0.708893 0.257329 0.226248 11.00000 -1.20000 AFIX 0 C17 1 0.755795 0.293565 0.312566 11.00000 0.02711 0.03616 = 0.02072 -0.00198 0.00730 0.00211 C18 1 0.760183 0.354645 0.292943 11.00000 0.03670 0.03727 = 0.02623 0.00343 0.01029 0.00632 C19 1 0.833794 0.386254 0.298431 11.00000 0.05000 0.03669 = 0.03902 0.00477 0.01666 -0.00361 AFIX 43 H19 2 0.838469 0.426938 0.285832 11.00000 -1.20000 AFIX 0 C20 1 0.899673 0.358878 0.321977 11.00000 0.03443 0.05237 = 0.04493 -0.00307 0.01037 -0.01104 AFIX 43 H20 2 0.948366 0.380864 0.324691 11.00000 -1.20000 AFIX 0 C21 1 0.893997 0.299264 0.341512 11.00000 0.02974 0.05202 = 0.03466 -0.00065 0.00369 0.00475 AFIX 43 H21 2 0.938959 0.281349 0.357565 11.00000 -1.20000 AFIX 0 C22 1 0.821675 0.264956 0.337688 11.00000 0.02835 0.03756 = 0.02612 -0.00031 0.00674 0.00456 C23 1 0.688877 0.386422 0.266029 11.00000 0.04888 0.04621 = 0.03373 0.01006 0.00439 0.01490 AFIX 13 H23 2 0.641073 0.359407 0.270181 11.00000 -1.20000 AFIX 0 C24 1 0.703773 0.394904 0.208083 11.00000 0.08518 0.07464 = 0.03572 0.01453 -0.00086 0.02696 AFIX 137 H24A 2 0.749308 0.422405 0.202915 11.00000 -1.50000 H24B 2 0.656219 0.412729 0.192340 11.00000 -1.50000 H24C 2 0.715123 0.354891 0.192698 11.00000 -1.50000 AFIX 0 C25 1 0.668770 0.449994 0.289615 11.00000 0.10709 0.07448 = 0.04495 0.00069 -0.00536 0.05431 AFIX 137 H25A 2 0.655895 0.444770 0.325483 11.00000 -1.50000 H25B 2 0.622914 0.467897 0.272017 11.00000 -1.50000 H25C 2 0.714830 0.477382 0.286212 11.00000 -1.50000 AFIX 0 C26 1 0.817752 0.199016 0.359110 11.00000 0.03196 0.03943 = 0.03780 0.00527 0.00463 0.00604 AFIX 13 H26 2 0.760236 0.187435 0.362138 11.00000 -1.20000 AFIX 0 C27 1 0.858191 0.152433 0.321841 11.00000 0.05461 0.04396 = 0.04803 0.00082 0.00548 0.01373 AFIX 137 H27A 2 0.831827 0.154641 0.288842 11.00000 -1.50000 H27B 2 0.853309 0.110688 0.335374 11.00000 -1.50000 H27C 2 0.914702 0.162867 0.318025 11.00000 -1.50000 AFIX 0 C28 1 0.855690 0.194581 0.412860 11.00000 0.05811 0.05435 = 0.03881 0.01068 0.00207 0.01319 AFIX 137 H28A 2 0.913099 0.202442 0.410565 11.00000 -1.50000 H28B 2 0.846745 0.153362 0.426646 11.00000 -1.50000 H28C 2 0.831039 0.225156 0.435108 11.00000 -1.50000 AFIX 0 C29 1 0.638377 0.285790 0.484902 11.00000 0.01899 0.02359 = 0.02067 -0.00012 0.00059 0.00295 C30 1 0.621632 0.175677 0.521660 11.00000 0.04168 0.02145 = 0.03005 -0.00260 -0.00359 0.00015 C31 1 0.639640 0.152430 0.467944 11.00000 0.08880 0.02239 = 0.03443 -0.00794 -0.00913 0.01269 AFIX 137 H31A 2 0.597734 0.166409 0.444843 11.00000 -1.50000 H31B 2 0.641441 0.107424 0.467999 11.00000 -1.50000 H31C 2 0.691213 0.168653 0.456779 11.00000 -1.50000 AFIX 0 C32 1 0.535273 0.155038 0.536363 11.00000 0.05854 0.03739 = 0.08743 -0.00843 0.01335 -0.01766 AFIX 137 H32A 2 0.525086 0.165384 0.571824 11.00000 -1.50000 H32B 2 0.530127 0.110552 0.531656 11.00000 -1.50000 H32C 2 0.496557 0.176262 0.514811 11.00000 -1.50000 AFIX 0 C33 1 0.685282 0.149144 0.558000 11.00000 0.07835 0.03174 = 0.04574 0.00338 -0.02721 0.00390 AFIX 137 H33A 2 0.738249 0.163320 0.547599 11.00000 -1.50000 H33B 2 0.683530 0.104156 0.556893 11.00000 -1.50000 H33C 2 0.674346 0.163165 0.592504 11.00000 -1.50000 AFIX 0 C34 1 0.615187 0.277228 0.574293 11.00000 0.04013 0.02929 = 0.01942 -0.00194 0.00523 -0.00373 C35 1 0.626700 0.377240 0.612340 11.00000 0.03635 0.02310 = 0.02044 -0.00210 0.00577 -0.00582 C36 1 0.696077 0.387122 0.641337 11.00000 0.03310 0.05215 = 0.03992 -0.01615 0.00169 -0.00032 AFIX 43 H36 2 0.744373 0.367182 0.632347 11.00000 -1.20000 AFIX 0 C37 1 0.693976 0.426473 0.683595 11.00000 0.04720 0.06695 = 0.04542 -0.02550 -0.00711 -0.00971 AFIX 43 H37 2 0.740794 0.432895 0.703049 11.00000 -1.20000 AFIX 0 C38 1 0.622696 0.456234 0.696998 11.00000 0.06587 0.04745 = 0.03760 -0.02213 0.00585 -0.00913 AFIX 43 H38 2 0.621452 0.482860 0.725405 11.00000 -1.20000 AFIX 0 C39 1 0.553134 0.446575 0.668311 11.00000 0.04406 0.04049 = 0.04593 -0.01367 0.01163 0.00037 AFIX 43 H39 2 0.504895 0.466488 0.677464 11.00000 -1.20000 AFIX 0 C40 1 0.555225 0.407180 0.625855 11.00000 0.03557 0.03350 = 0.03179 -0.00517 0.00068 -0.00194 AFIX 43 H40 2 0.508401 0.400857 0.606386 11.00000 -1.20000 AFIX 0 C41 1 0.649913 0.459360 0.481408 11.00000 0.04993 0.02457 = 0.04071 0.00892 0.01295 0.00710 C42 1 0.619154 0.494422 0.434430 11.00000 0.07186 0.05102 = 0.06607 0.02876 0.01680 0.02235 AFIX 137 H42A 2 0.611624 0.465505 0.406446 11.00000 -1.50000 H42B 2 0.658138 0.525774 0.424636 11.00000 -1.50000 H42C 2 0.568216 0.514197 0.442452 11.00000 -1.50000 AFIX 0 C43 1 0.644318 0.502688 0.528383 11.00000 0.07102 0.02517 = 0.06256 -0.00708 0.02726 -0.00210 AFIX 137 H43A 2 0.588187 0.511065 0.535992 11.00000 -1.50000 H43B 2 0.671843 0.541397 0.521070 11.00000 -1.50000 H43C 2 0.669417 0.482768 0.557537 11.00000 -1.50000 AFIX 0 C44 1 0.736398 0.430723 0.474999 11.00000 0.04030 0.02423 = 0.03616 0.00492 0.00946 -0.00246 C45 1 0.752885 0.407751 0.420183 11.00000 0.05803 0.04024 = 0.03995 0.00619 0.02081 0.00601 AFIX 137 H45A 2 0.800778 0.381966 0.420014 11.00000 -1.50000 H45B 2 0.761003 0.443135 0.397865 11.00000 -1.50000 H45C 2 0.707238 0.383711 0.408213 11.00000 -1.50000 AFIX 0 C46 1 0.806483 0.472585 0.492033 11.00000 0.05809 0.03602 = 0.07224 0.00033 0.01325 -0.01259 AFIX 137 H46A 2 0.800995 0.481959 0.528089 11.00000 -1.50000 H46B 2 0.805502 0.510877 0.472558 11.00000 -1.50000 H46C 2 0.857144 0.451316 0.486193 11.00000 -1.50000 AFIX 0 PART 1 C5 1 0.494018 0.211923 0.362115 10.63000 0.01932 0.04773 = 0.02190 0.00301 -0.00134 -0.00723 C6 1 0.457878 0.266527 0.380998 10.63000 0.01543 0.05383 = 0.02347 -0.00409 -0.00057 -0.00255 C7 1 0.395519 0.261373 0.416889 10.63000 0.02261 0.06785 = 0.04386 -0.00740 0.00438 -0.00702 AFIX 43 H7 2 0.372012 0.297441 0.430493 10.63000 -1.20000 AFIX 0 C8 1 0.367888 0.202833 0.432680 10.63000 0.02704 0.07745 = 0.04574 -0.00247 0.00973 -0.01702 AFIX 43 H8 2 0.326116 0.199961 0.456771 10.63000 -1.20000 AFIX 0 C9 1 0.402372 0.148669 0.412648 10.63000 0.02764 0.06431 = 0.04076 -0.00109 0.00200 -0.01816 AFIX 43 H9 2 0.382910 0.109560 0.422660 10.63000 -1.20000 AFIX 0 C10 1 0.466181 0.153025 0.377522 10.63000 0.02679 0.05280 = 0.02953 -0.00629 -0.00519 -0.00625 C11 1 0.478210 0.331306 0.360737 10.63000 0.02267 0.04561 = 0.04397 -0.00308 -0.00079 0.01121 AFIX 13 H11 2 0.537322 0.333344 0.356016 10.63000 -1.20000 AFIX 0 C12 1 0.438650 0.342266 0.307975 10.63000 0.06754 0.06233 = 0.04792 0.00332 -0.01155 0.02224 AFIX 137 H12A 2 0.456908 0.310727 0.284212 10.63000 -1.50000 H12B 2 0.453712 0.382963 0.295326 10.63000 -1.50000 H12C 2 0.380546 0.339976 0.311331 10.63000 -1.50000 AFIX 0 C13 1 0.453540 0.386100 0.395509 10.63000 0.06872 0.05394 = 0.05272 -0.00752 -0.01165 0.01406 AFIX 137 H13A 2 0.395426 0.386690 0.399268 10.63000 -1.50000 H13B 2 0.471329 0.424793 0.380292 10.63000 -1.50000 H13C 2 0.478388 0.381191 0.428783 10.63000 -1.50000 AFIX 0 C14 1 0.500607 0.092150 0.356569 10.63000 0.03830 0.05059 = 0.05199 -0.00469 -0.00979 -0.01008 AFIX 13 H14 2 0.552802 0.101758 0.340075 10.63000 -1.20000 AFIX 0 C15 1 0.444674 0.063191 0.315367 10.63000 0.06217 0.05595 = 0.05486 -0.01597 -0.01022 -0.01531 AFIX 137 H15A 2 0.394210 0.050811 0.331002 10.63000 -1.50000 H15B 2 0.470684 0.027123 0.300545 10.63000 -1.50000 H15C 2 0.434226 0.093566 0.288843 10.63000 -1.50000 AFIX 0 C16 1 0.516000 0.041263 0.397366 10.63000 0.08182 0.04405 = 0.08065 0.00165 -0.03382 -0.01415 AFIX 137 H16A 2 0.548325 0.058361 0.424822 10.63000 -1.50000 H16B 2 0.544367 0.006718 0.381845 10.63000 -1.50000 H16C 2 0.464927 0.026907 0.410926 10.63000 -1.50000 AFIX 0 PART 0 PART 2 C5A 1 0.495287 0.199229 0.360100 10.37000 0.02372 0.05783 = 0.02422 -0.00868 -0.00958 0.00205 C6A 1 0.448874 0.246006 0.383327 10.37000 0.01645 0.07704 = 0.04023 -0.00489 -0.00842 -0.00451 C7A 1 0.393999 0.227094 0.421068 10.37000 0.02385 0.08797 = 0.04049 -0.00122 0.00740 -0.00414 AFIX 43 H7A 2 0.363961 0.256493 0.439506 10.37000 -1.20000 AFIX 0 C8A 1 0.384975 0.163417 0.430659 10.37000 0.02480 0.08983 = 0.04488 -0.00376 0.00694 -0.01200 AFIX 43 H8A 2 0.348211 0.150808 0.455887 10.37000 -1.20000 AFIX 0 C9A 1 0.428448 0.117698 0.404229 10.37000 0.03386 0.08473 = 0.04396 -0.00838 -0.00155 -0.01631 AFIX 43 H9A 2 0.419386 0.075496 0.411257 10.37000 -1.20000 AFIX 0 C10A 1 0.485450 0.135000 0.367303 10.37000 0.02682 0.05688 = 0.02582 -0.00402 -0.00163 -0.01622 C11A 1 0.453878 0.314164 0.367061 10.37000 0.02287 0.09679 = 0.06333 -0.02591 -0.00295 0.02807 AFIX 13 H11A 2 0.506366 0.321286 0.350094 10.37000 -1.20000 AFIX 0 C12A 1 0.385532 0.327623 0.328279 10.37000 0.10272 0.08963 = 0.08426 -0.00710 -0.03690 0.03570 AFIX 137 H12D 2 0.333758 0.322797 0.344972 10.37000 -1.50000 H12E 2 0.389325 0.298739 0.299970 10.37000 -1.50000 H12F 2 0.390749 0.369752 0.315632 10.37000 -1.50000 AFIX 0 C13A 1 0.445577 0.360255 0.412164 10.37000 0.06906 0.07729 = 0.08026 -0.02084 -0.01950 0.02070 AFIX 137 H13D 2 0.453754 0.402276 0.399910 10.37000 -1.50000 H13E 2 0.485619 0.350659 0.437950 10.37000 -1.50000 H13F 2 0.392160 0.356687 0.426870 10.37000 -1.50000 AFIX 0 C14A 1 0.530951 0.083840 0.338805 10.37000 0.05151 0.03580 = 0.04360 -0.00389 -0.00793 -0.01170 AFIX 13 H14A 2 0.569012 0.104377 0.315103 10.37000 -1.20000 AFIX 0 C15A 1 0.471969 0.044640 0.306033 10.37000 0.07459 0.07159 = 0.04623 -0.01683 -0.00390 -0.03489 AFIX 137 H15D 2 0.432113 0.025471 0.328048 10.37000 -1.50000 H15E 2 0.501741 0.012636 0.288075 10.37000 -1.50000 H15F 2 0.445192 0.071313 0.281495 10.37000 -1.50000 AFIX 0 C16A 1 0.580752 0.039969 0.373441 10.37000 0.12272 0.06659 = 0.08851 -0.02211 -0.03602 0.01663 AFIX 137 H16D 2 0.627682 0.061869 0.386170 10.37000 -1.50000 H16E 2 0.597897 0.004094 0.353876 10.37000 -1.50000 H16F 2 0.547860 0.026473 0.401965 10.37000 -1.50000 AFIX 0 PART 0 B1 3 0.650012 0.356104 0.511006 11.00000 0.02933 0.02421 = 0.01950 0.00193 0.00249 0.00273 HKLF 4 REM e20djl04 REM R1 = 0.0512 for 7591 Fo > 4sig(Fo) and 0.0996 for all 11957 data REM 623 parameters refined using 293 restraints END WGHT 0.0389 7.7070 REM Highest difference peak 0.719, deepest hole -0.394, 1-sigma level 0.060 Q1 1 0.6344 0.2211 0.4132 11.00000 0.05 0.72 Q2 1 0.6233 0.1890 0.2406 11.00000 0.05 0.67 Q3 1 0.6505 0.2408 0.6181 11.00000 0.05 0.54 REM The information below was added by Olex2. REM REM R1 = 0.0512 for 7591 Fo > 4sig(Fo) and 0.0996 for all 83523 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.72, deepest hole -0.39 REM Mean Shift 0, Max Shift 0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0996 REM R1_gt = 0.0512 REM wR_ref = 0.1241 REM GOOF = 1.052 REM Shift_max = 0.001 REM Shift_mean = 0 REM Reflections_all = 83523 REM Reflections_gt = 7591 REM Parameters = n/a REM Hole = -0.39 REM Peak = 0.72 REM Flack = n/a ; _cod_data_source_file d1dt03540a2.cif _cod_data_source_block e20djl04-cpd5 _cod_database_code 7708614 _shelxl_version_number 2014-3 _chemical_oxdiff_usercomment 'pale yellow blocks' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N1-C5 \\sim N1-C5A with sigma of 0.005 C6-C5 \\sim C7-C6 \\sim C8-C7 \\sim C9-C8 \\sim C9-C10 \\sim C5-C10 \\sim C6A-C5A \\sim C7A-C6A \\sim C8A-C7A \\sim C9A-C8A \\sim C9A-C10A \\sim C5A-C10A with sigma of 0.005 C6-C11 \\sim C6A-C11A \\sim C14A-C10A \\sim C14-C10 with sigma of 0.005 C13-C11 \\sim C13A-C11A \\sim C12A-C11A \\sim C12-C11 \\sim C16A-C14A \\sim C16-C14 \\sim C15A-C14A ~ C15-C14 with sigma of 0.005 3. Uiso/Uaniso restraints and constraints C10A \\sim C10 \\sim C9A \\sim C9 \\sim C8A \\sim C8 \\sim C7A \\sim C6A \\sim C5A \\sim C5 \\sim C6: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.01 C14A \\sim C14 \\sim C11A \\sim C11: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.01 C15A \\sim C15 \\sim C16A \\sim C16 \\sim C13A \\sim C13 \\sim C12 \\sim C12A: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.01 4. Others Fixed Sof: C5(0.63) C6(0.63) C7(0.63) H7(0.63) C8(0.63) H8(0.63) C9(0.63) H9(0.63) C10(0.63) C11(0.63) H11(0.63) C12(0.63) H12A(0.63) H12B(0.63) H12C(0.63) C13(0.63) H13A(0.63) H13B(0.63) H13C(0.63) C14(0.63) H14(0.63) C15(0.63) H15A(0.63) H15B(0.63) H15C(0.63) C16(0.63) H16A(0.63) H16B(0.63) H16C(0.63) C5A(0.37) C6A(0.37) C7A(0.37) H7A(0.37) C8A(0.37) H8A(0.37) C9A(0.37) H9A(0.37) C10A(0.37) C11A(0.37) H11A(0.37) C12A(0.37) H12D(0.37) H12E(0.37) H12F(0.37) C13A(0.37) H13D(0.37) H13E(0.37) H13F(0.37) C14A(0.37) H14A(0.37) C15A(0.37) H15D(0.37) H15E(0.37) H15F(0.37) C16A(0.37) H16D(0.37) H16E(0.37) H16F(0.37) 5.a Ternary CH refined with riding coordinates: C23(H23), C26(H26), C11(H11), C14(H14), C11A(H11A), C14A(H14A) 5.b Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B) 5.c Aromatic/amide H refined with riding coordinates: C19(H19), C20(H20), C21(H21), C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C7(H7), C8(H8), C9(H9), C7A(H7A), C8A(H8A), C9A(H9A) 5.d Idealised Me refined as rotating group: C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B, H28C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C42(H42A, H42B,H42C), C43(H43A,H43B,H43C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B, H16C), C12A(H12D,H12E,H12F), C13A(H13D,H13E,H13F), C15A(H15D,H15E,H15F), C16A(H16D,H16E,H16F) ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.63818(2) 0.26833(2) 0.41205(2) 0.02294(8) Uani 1 1 d . . . . . O1 O 0.59506(15) 0.24804(9) 0.61222(7) 0.0551(6) Uani 1 1 d . . . . . O2 O 0.60021(10) 0.40521(8) 0.48966(6) 0.0309(4) Uani 1 1 d . . . . . O3 O 0.73394(9) 0.37748(7) 0.50829(6) 0.0285(4) Uani 1 1 d . . . . . N1 N 0.55838(11) 0.21761(9) 0.32390(7) 0.0282(4) Uani 1 1 d D . . . . N2 N 0.68274(11) 0.25750(10) 0.30252(7) 0.0288(4) Uani 1 1 d . . . . . N3 N 0.62608(11) 0.24636(9) 0.52305(7) 0.0243(4) Uani 1 1 d . . . . . N4 N 0.62892(12) 0.33757(9) 0.56825(7) 0.0265(4) Uani 1 1 d . . . . . C1 C 0.62679(12) 0.24752(10) 0.33896(8) 0.0231(4) Uani 1 1 d . . . . . C2 C 0.53675(17) 0.20180(16) 0.27007(10) 0.0472(7) Uani 1 1 d . . . . . H2A H 0.5426 0.1569 0.2650 0.057 Uiso 1 1 calc R . . . . H2B H 0.4802 0.2127 0.2640 0.057 Uiso 1 1 calc R . . . . C3 C 0.58825(19) 0.23502(19) 0.23271(11) 0.0601(9) Uani 1 1 d . . . . . H3A H 0.5708 0.2784 0.2301 0.072 Uiso 1 1 calc R . . . . H3B H 0.5827 0.2158 0.1990 0.072 Uiso 1 1 calc R . . . . C4 C 0.67567(16) 0.23257(15) 0.24953(10) 0.0414(6) Uani 1 1 d . . . . . H4A H 0.6950 0.1896 0.2485 0.050 Uiso 1 1 calc R . . . . H4B H 0.7089 0.2573 0.2262 0.050 Uiso 1 1 calc R . . . . C17 C 0.75580(14) 0.29356(12) 0.31257(9) 0.0280(5) Uani 1 1 d . . . . . C18 C 0.76018(15) 0.35464(12) 0.29294(9) 0.0334(6) Uani 1 1 d . . . . . C19 C 0.83379(17) 0.38625(13) 0.29843(11) 0.0419(7) Uani 1 1 d . . . . . H19 H 0.8385 0.4269 0.2858 0.050 Uiso 1 1 calc R . . . . C20 C 0.89967(17) 0.35888(14) 0.32198(11) 0.0439(7) Uani 1 1 d . . . . . H20 H 0.9484 0.3809 0.3247 0.053 Uiso 1 1 calc R . . . . C21 C 0.89400(16) 0.29926(14) 0.34151(10) 0.0388(6) Uani 1 1 d . . . . . H21 H 0.9390 0.2813 0.3576 0.047 Uiso 1 1 calc R . . . . C22 C 0.82168(14) 0.26496(12) 0.33769(9) 0.0307(5) Uani 1 1 d . . . . . C23 C 0.68888(18) 0.38642(14) 0.26603(10) 0.0429(7) Uani 1 1 d . . . . . H23 H 0.6411 0.3594 0.2702 0.052 Uiso 1 1 calc R . . . . C24 C 0.7038(2) 0.39490(17) 0.20808(11) 0.0652(10) Uani 1 1 d . . . . . H24A H 0.7493 0.4224 0.2029 0.098 Uiso 1 1 calc GR . . . . H24B H 0.6562 0.4127 0.1923 0.098 Uiso 1 1 calc GR . . . . H24C H 0.7151 0.3549 0.1927 0.098 Uiso 1 1 calc GR . . . . C25 C 0.6688(3) 0.44999(17) 0.28962(13) 0.0755(12) Uani 1 1 d . . . . . H25A H 0.6559 0.4448 0.3255 0.113 Uiso 1 1 calc GR . . . . H25B H 0.6229 0.4679 0.2720 0.113 Uiso 1 1 calc GR . . . . H25C H 0.7148 0.4774 0.2862 0.113 Uiso 1 1 calc GR . . . . C26 C 0.81775(15) 0.19902(13) 0.35911(10) 0.0364(6) Uani 1 1 d . . . . . H26 H 0.7602 0.1874 0.3621 0.044 Uiso 1 1 calc R . . . . C27 C 0.85819(18) 0.15243(14) 0.32184(12) 0.0489(7) Uani 1 1 d . . . . . H27A H 0.8318 0.1546 0.2888 0.073 Uiso 1 1 calc GR . . . . H27B H 0.8533 0.1107 0.3354 0.073 Uiso 1 1 calc GR . . . . H27C H 0.9147 0.1629 0.3180 0.073 Uiso 1 1 calc GR . . . . C28 C 0.85569(19) 0.19458(15) 0.41286(11) 0.0504(7) Uani 1 1 d . . . . . H28A H 0.9131 0.2024 0.4106 0.076 Uiso 1 1 calc GR . . . . H28B H 0.8467 0.1534 0.4266 0.076 Uiso 1 1 calc GR . . . . H28C H 0.8310 0.2252 0.4351 0.076 Uiso 1 1 calc GR . . . . C29 C 0.63838(12) 0.28579(10) 0.48490(8) 0.0211(4) Uani 1 1 d . . . . . C30 C 0.62163(15) 0.17568(11) 0.52166(10) 0.0311(5) Uani 1 1 d . . . . . C31 C 0.6396(2) 0.15243(12) 0.46794(10) 0.0485(8) Uani 1 1 d . . . . . H31A H 0.5977 0.1664 0.4448 0.073 Uiso 1 1 calc GR . . . . H31B H 0.6414 0.1074 0.4680 0.073 Uiso 1 1 calc GR . . . . H31C H 0.6912 0.1687 0.4568 0.073 Uiso 1 1 calc GR . . . . C32 C 0.5353(2) 0.15504(14) 0.53636(15) 0.0611(9) Uani 1 1 d . . . . . H32A H 0.5251 0.1654 0.5718 0.092 Uiso 1 1 calc GR . . . . H32B H 0.5301 0.1106 0.5317 0.092 Uiso 1 1 calc GR . . . . H32C H 0.4966 0.1763 0.5148 0.092 Uiso 1 1 calc GR . . . . C33 C 0.6853(2) 0.14914(13) 0.55800(12) 0.0519(8) Uani 1 1 d . . . . . H33A H 0.7382 0.1633 0.5476 0.078 Uiso 1 1 calc GR . . . . H33B H 0.6835 0.1042 0.5569 0.078 Uiso 1 1 calc GR . . . . H33C H 0.6743 0.1632 0.5925 0.078 Uiso 1 1 calc GR . . . . C34 C 0.61519(15) 0.27723(11) 0.57429(9) 0.0296(5) Uani 1 1 d . . . . . C35 C 0.62670(14) 0.37724(11) 0.61234(9) 0.0266(5) Uani 1 1 d . . . . . C36 C 0.69608(16) 0.38712(14) 0.64134(11) 0.0417(7) Uani 1 1 d . . . . . H36 H 0.7444 0.3672 0.6323 0.050 Uiso 1 1 calc R . . . . C37 C 0.69398(18) 0.42647(15) 0.68360(12) 0.0532(8) Uani 1 1 d . . . . . H37 H 0.7408 0.4329 0.7030 0.064 Uiso 1 1 calc R . . . . C38 C 0.62270(19) 0.45623(14) 0.69700(11) 0.0503(8) Uani 1 1 d . . . . . H38 H 0.6215 0.4829 0.7254 0.060 Uiso 1 1 calc R . . . . C39 C 0.55313(17) 0.44658(13) 0.66831(11) 0.0435(7) Uani 1 1 d . . . . . H39 H 0.5049 0.4665 0.6775 0.052 Uiso 1 1 calc R . . . . C40 C 0.55523(15) 0.40718(12) 0.62586(10) 0.0336(6) Uani 1 1 d . . . . . H40 H 0.5084 0.4009 0.6064 0.040 Uiso 1 1 calc R . . . . C41 C 0.64991(17) 0.45936(12) 0.48141(11) 0.0384(6) Uani 1 1 d . . . . . C42 C 0.6192(2) 0.49442(16) 0.43443(13) 0.0630(10) Uani 1 1 d . . . . . H42A H 0.6116 0.4655 0.4064 0.094 Uiso 1 1 calc GR . . . . H42B H 0.6581 0.5258 0.4246 0.094 Uiso 1 1 calc GR . . . . H42C H 0.5682 0.5142 0.4425 0.094 Uiso 1 1 calc GR . . . . C43 C 0.6443(2) 0.50269(13) 0.52838(12) 0.0529(8) Uani 1 1 d . . . . . H43A H 0.5882 0.5111 0.5360 0.079 Uiso 1 1 calc GR . . . . H43B H 0.6718 0.5414 0.5211 0.079 Uiso 1 1 calc GR . . . . H43C H 0.6694 0.4828 0.5575 0.079 Uiso 1 1 calc GR . . . . C44 C 0.73640(15) 0.43072(11) 0.47500(10) 0.0336(6) Uani 1 1 d . . . . . C45 C 0.75288(19) 0.40775(14) 0.42018(10) 0.0461(7) Uani 1 1 d . . . . . H45A H 0.8008 0.3820 0.4200 0.069 Uiso 1 1 calc GR . . . . H45B H 0.7610 0.4431 0.3979 0.069 Uiso 1 1 calc GR . . . . H45C H 0.7072 0.3837 0.4082 0.069 Uiso 1 1 calc GR . . . . C46 C 0.80648(19) 0.47259(14) 0.49203(13) 0.0555(8) Uani 1 1 d . . . . . H46A H 0.8010 0.4820 0.5281 0.083 Uiso 1 1 calc GR . . . . H46B H 0.8055 0.5109 0.4726 0.083 Uiso 1 1 calc GR . . . . H46C H 0.8571 0.4513 0.4862 0.083 Uiso 1 1 calc GR . . . . C5 C 0.4940(10) 0.2119(3) 0.3621(7) 0.0297(16) Uani 0.63 1 d D U P A 1 C6 C 0.4579(5) 0.2665(3) 0.3810(3) 0.0309(14) Uani 0.63 1 d D U P A 1 C7 C 0.3955(3) 0.2614(3) 0.4169(2) 0.0448(13) Uani 0.63 1 d D . P A 1 H7 H 0.3720 0.2974 0.4305 0.054 Uiso 0.63 1 calc R . P A 1 C8 C 0.3679(3) 0.2028(2) 0.4327(2) 0.0501(15) Uani 0.63 1 d D U P A 1 H8 H 0.3261 0.2000 0.4568 0.060 Uiso 0.63 1 calc R . P A 1 C9 C 0.4024(3) 0.1487(3) 0.4126(2) 0.0442(15) Uani 0.63 1 d D U P A 1 H9 H 0.3829 0.1096 0.4227 0.053 Uiso 0.63 1 calc R . P A 1 C10 C 0.4662(4) 0.1530(3) 0.3775(3) 0.0364(14) Uani 0.63 1 d D U P A 1 C11 C 0.4782(3) 0.3313(3) 0.3607(2) 0.0374(15) Uani 0.63 1 d D U P A 1 H11 H 0.5373 0.3333 0.3560 0.045 Uiso 0.63 1 calc R . P A 1 C12 C 0.4387(4) 0.3423(3) 0.30798(19) 0.0593(15) Uani 0.63 1 d D U P A 1 H12A H 0.4569 0.3107 0.2842 0.089 Uiso 0.63 1 calc GR . P A 1 H12B H 0.4537 0.3830 0.2953 0.089 Uiso 0.63 1 calc GR . P A 1 H12C H 0.3805 0.3400 0.3113 0.089 Uiso 0.63 1 calc GR . P A 1 C13 C 0.4535(6) 0.3861(3) 0.3955(3) 0.0585(18) Uani 0.63 1 d D U P A 1 H13A H 0.3954 0.3867 0.3993 0.088 Uiso 0.63 1 calc GR . P A 1 H13B H 0.4713 0.4248 0.3803 0.088 Uiso 0.63 1 calc GR . P A 1 H13C H 0.4784 0.3812 0.4288 0.088 Uiso 0.63 1 calc GR . P A 1 C14 C 0.5006(4) 0.0922(3) 0.3566(2) 0.0470(15) Uani 0.63 1 d D U P A 1 H14 H 0.5528 0.1018 0.3401 0.056 Uiso 0.63 1 calc R . P A 1 C15 C 0.4447(4) 0.0632(4) 0.3154(3) 0.058(2) Uani 0.63 1 d D U P A 1 H15A H 0.3942 0.0508 0.3310 0.086 Uiso 0.63 1 calc GR . P A 1 H15B H 0.4707 0.0271 0.3005 0.086 Uiso 0.63 1 calc GR . P A 1 H15C H 0.4342 0.0936 0.2888 0.086 Uiso 0.63 1 calc GR . P A 1 C16 C 0.5160(4) 0.0413(3) 0.3974(2) 0.0688(17) Uani 0.63 1 d D U P A 1 H16A H 0.5483 0.0584 0.4248 0.103 Uiso 0.63 1 calc GR . P A 1 H16B H 0.5444 0.0067 0.3818 0.103 Uiso 0.63 1 calc GR . P A 1 H16C H 0.4649 0.0269 0.4109 0.103 Uiso 0.63 1 calc GR . P A 1 C5A C 0.4953(17) 0.1992(5) 0.3601(12) 0.035(3) Uani 0.37 1 d D U P A 2 C6A C 0.4489(10) 0.2460(5) 0.3833(7) 0.045(3) Uani 0.37 1 d D U P A 2 C7A C 0.3940(7) 0.2271(5) 0.4211(4) 0.051(3) Uani 0.37 1 d D U P A 2 H7A H 0.3640 0.2565 0.4395 0.061 Uiso 0.37 1 calc R . P A 2 C8A C 0.3850(7) 0.1634(5) 0.4307(4) 0.053(3) Uani 0.37 1 d D U P A 2 H8A H 0.3482 0.1508 0.4559 0.064 Uiso 0.37 1 calc R . P A 2 C9A C 0.4284(5) 0.1177(5) 0.4042(3) 0.054(2) Uani 0.37 1 d D U P A 2 H9A H 0.4194 0.0755 0.4113 0.065 Uiso 0.37 1 calc R . P A 2 C10A C 0.4855(7) 0.1350(4) 0.3673(4) 0.037(2) Uani 0.37 1 d D U P A 2 C11A C 0.4539(6) 0.3142(6) 0.3671(4) 0.061(4) Uani 0.37 1 d D U P A 2 H11A H 0.5064 0.3213 0.3501 0.073 Uiso 0.37 1 calc R . P A 2 C12A C 0.3855(8) 0.3276(7) 0.3283(5) 0.092(3) Uani 0.37 1 d D U P A 2 H12D H 0.3338 0.3228 0.3450 0.138 Uiso 0.37 1 calc GR . P A 2 H12E H 0.3893 0.2987 0.3000 0.138 Uiso 0.37 1 calc GR . P A 2 H12F H 0.3907 0.3698 0.3156 0.138 Uiso 0.37 1 calc GR . P A 2 C13A C 0.4456(11) 0.3603(6) 0.4122(5) 0.076(4) Uani 0.37 1 d D U P A 2 H13D H 0.4538 0.4023 0.3999 0.113 Uiso 0.37 1 calc GR . P A 2 H13E H 0.4856 0.3507 0.4379 0.113 Uiso 0.37 1 calc GR . P A 2 H13F H 0.3922 0.3567 0.4269 0.113 Uiso 0.37 1 calc GR . P A 2 C14A C 0.5310(6) 0.0838(4) 0.3388(3) 0.044(2) Uani 0.37 1 d D U P A 2 H14A H 0.5690 0.1044 0.3151 0.052 Uiso 0.37 1 calc R . P A 2 C15A C 0.4720(7) 0.0446(8) 0.3060(6) 0.064(4) Uani 0.37 1 d D U P A 2 H15D H 0.4321 0.0255 0.3280 0.096 Uiso 0.37 1 calc GR . P A 2 H15E H 0.5017 0.0126 0.2881 0.096 Uiso 0.37 1 calc GR . P A 2 H15F H 0.4452 0.0713 0.2815 0.096 Uiso 0.37 1 calc GR . P A 2 C16A C 0.5808(9) 0.0400(5) 0.3734(5) 0.093(3) Uani 0.37 1 d D U P A 2 H16D H 0.6277 0.0619 0.3862 0.139 Uiso 0.37 1 calc GR . P A 2 H16E H 0.5979 0.0041 0.3539 0.139 Uiso 0.37 1 calc GR . P A 2 H16F H 0.5479 0.0265 0.4020 0.139 Uiso 0.37 1 calc GR . P A 2 B1 B 0.65001(15) 0.35610(12) 0.51101(10) 0.0243(5) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02367(13) 0.02830(14) 0.01685(13) -0.00094(11) 0.00039(11) 0.00397(12) O1 0.1058(18) 0.0360(11) 0.0234(10) 0.0014(8) 0.0183(11) -0.0193(11) O2 0.0326(9) 0.0269(9) 0.0332(9) 0.0037(7) 0.0033(7) 0.0068(7) O3 0.0292(8) 0.0237(8) 0.0326(9) 0.0035(7) 0.0036(7) 0.0004(7) N1 0.0229(9) 0.0407(12) 0.0210(10) -0.0045(8) -0.0006(8) 0.0013(8) N2 0.0276(10) 0.0391(12) 0.0197(10) -0.0017(8) 0.0035(8) 0.0022(9) N3 0.0289(10) 0.0225(9) 0.0216(9) -0.0034(7) -0.0002(8) -0.0009(8) N4 0.0376(11) 0.0233(10) 0.0186(9) -0.0031(8) 0.0053(8) -0.0018(8) C1 0.0248(10) 0.0253(11) 0.0192(10) -0.0008(8) 0.0006(9) 0.0079(9) C2 0.0407(15) 0.073(2) 0.0281(14) -0.0164(14) -0.0039(12) -0.0067(15) C3 0.0543(18) 0.100(3) 0.0257(14) -0.0101(17) -0.0020(13) -0.0085(19) C4 0.0421(14) 0.0597(18) 0.0224(12) -0.0075(13) 0.0029(11) 0.0009(14) C17 0.0271(11) 0.0362(13) 0.0207(11) -0.0020(10) 0.0073(9) 0.0021(10) C18 0.0367(13) 0.0373(14) 0.0262(13) 0.0034(11) 0.0103(10) 0.0063(11) C19 0.0500(16) 0.0367(15) 0.0390(16) 0.0048(12) 0.0167(13) -0.0036(13) C20 0.0344(14) 0.0524(18) 0.0449(17) -0.0031(14) 0.0104(12) -0.0110(13) C21 0.0297(12) 0.0520(17) 0.0347(14) -0.0007(13) 0.0037(11) 0.0047(12) C22 0.0283(11) 0.0376(14) 0.0261(12) -0.0003(11) 0.0067(9) 0.0046(11) C23 0.0489(16) 0.0462(17) 0.0337(15) 0.0101(12) 0.0044(12) 0.0149(13) C24 0.085(2) 0.075(2) 0.0357(17) 0.0145(16) -0.0009(17) 0.027(2) C25 0.107(3) 0.074(3) 0.045(2) 0.0007(18) -0.0054(19) 0.054(2) C26 0.0320(13) 0.0394(15) 0.0378(15) 0.0053(12) 0.0046(11) 0.0060(11) C27 0.0546(18) 0.0440(17) 0.0480(17) 0.0008(14) 0.0055(14) 0.0137(14) C28 0.0581(18) 0.0543(18) 0.0388(16) 0.0107(14) 0.0021(14) 0.0132(15) C29 0.0190(9) 0.0236(11) 0.0207(10) -0.0001(8) 0.0006(9) 0.0029(9) C30 0.0417(14) 0.0214(12) 0.0301(13) -0.0026(10) -0.0036(10) 0.0001(10) C31 0.089(2) 0.0224(13) 0.0344(15) -0.0079(11) -0.0091(15) 0.0127(14) C32 0.059(2) 0.0374(17) 0.087(3) -0.0084(17) 0.0133(18) -0.0177(15) C33 0.078(2) 0.0317(15) 0.0457(18) 0.0034(13) -0.0272(16) 0.0039(15) C34 0.0401(13) 0.0293(13) 0.0194(11) -0.0019(9) 0.0052(9) -0.0037(10) C35 0.0363(13) 0.0231(11) 0.0204(11) -0.0021(9) 0.0058(9) -0.0058(10) C36 0.0331(13) 0.0522(18) 0.0399(16) -0.0162(13) 0.0017(12) -0.0003(12) C37 0.0472(17) 0.067(2) 0.0454(18) -0.0255(16) -0.0071(14) -0.0097(15) C38 0.066(2) 0.0474(17) 0.0376(16) -0.0221(13) 0.0059(14) -0.0091(15) C39 0.0441(15) 0.0405(16) 0.0459(17) -0.0137(13) 0.0116(13) 0.0004(13) C40 0.0356(13) 0.0335(14) 0.0318(13) -0.0052(11) 0.0007(11) -0.0019(11) C41 0.0499(16) 0.0246(13) 0.0407(15) 0.0089(11) 0.0130(12) 0.0071(12) C42 0.072(2) 0.051(2) 0.066(2) 0.0288(17) 0.0168(18) 0.0224(17) C43 0.071(2) 0.0252(14) 0.063(2) -0.0071(13) 0.0273(17) -0.0021(14) C44 0.0403(14) 0.0242(13) 0.0362(14) 0.0049(11) 0.0095(11) -0.0025(11) C45 0.0580(17) 0.0402(16) 0.0399(16) 0.0062(13) 0.0208(14) 0.0060(14) C46 0.0581(19) 0.0360(17) 0.072(2) 0.0003(15) 0.0133(17) -0.0126(14) C5 0.019(3) 0.048(3) 0.022(3) 0.003(3) -0.001(2) -0.007(3) C6 0.015(3) 0.054(4) 0.023(2) -0.004(3) -0.0006(18) -0.003(3) C7 0.023(2) 0.068(4) 0.044(3) -0.007(3) 0.004(2) -0.007(3) C8 0.027(3) 0.077(4) 0.046(3) -0.002(3) 0.010(2) -0.017(3) C9 0.028(4) 0.064(4) 0.041(4) -0.001(3) 0.002(3) -0.018(3) C10 0.027(3) 0.053(4) 0.030(3) -0.006(3) -0.005(2) -0.006(3) C11 0.023(3) 0.046(3) 0.044(3) -0.003(2) -0.001(2) 0.011(2) C12 0.068(4) 0.062(4) 0.048(3) 0.003(3) -0.012(3) 0.022(3) C13 0.069(4) 0.054(4) 0.053(4) -0.008(3) -0.012(3) 0.014(4) C14 0.038(3) 0.051(4) 0.052(4) -0.005(3) -0.010(3) -0.010(3) C15 0.062(4) 0.056(5) 0.055(4) -0.016(3) -0.010(4) -0.015(3) C16 0.082(4) 0.044(3) 0.081(4) 0.002(3) -0.034(3) -0.014(3) C5A 0.024(5) 0.058(6) 0.024(5) -0.009(6) -0.010(4) 0.002(6) C6A 0.016(4) 0.077(7) 0.040(5) -0.005(6) -0.008(4) -0.005(6) C7A 0.024(4) 0.088(7) 0.040(5) -0.001(6) 0.007(4) -0.004(6) C8A 0.025(5) 0.090(7) 0.045(6) -0.004(6) 0.007(4) -0.012(5) C9A 0.034(5) 0.085(7) 0.044(5) -0.008(5) -0.002(4) -0.016(5) C10A 0.027(5) 0.057(6) 0.026(5) -0.004(5) -0.002(3) -0.016(5) C11A 0.023(6) 0.097(11) 0.063(7) -0.026(7) -0.003(5) 0.028(6) C12A 0.103(8) 0.090(7) 0.084(7) -0.007(6) -0.037(6) 0.036(7) C13A 0.069(6) 0.077(8) 0.080(8) -0.021(6) -0.020(6) 0.021(7) C14A 0.052(6) 0.036(5) 0.044(6) -0.004(4) -0.008(4) -0.012(4) C15A 0.075(8) 0.072(9) 0.046(6) -0.017(5) -0.004(6) -0.035(6) C16A 0.123(8) 0.067(6) 0.089(7) -0.022(6) -0.036(7) 0.017(6) B1 0.0293(13) 0.0242(13) 0.0195(12) 0.0019(10) 0.0025(10) 0.0027(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C29 Cu1 C1 174.23(9) . . ? C41 O2 B1 108.66(18) . . ? C44 O3 B1 107.79(18) . . ? C1 N1 C2 125.5(2) . . ? C1 N1 C5 116.6(8) . . ? C1 N1 C5A 122.3(15) . . ? C5 N1 C2 116.7(9) . . ? C5A N1 C2 112.1(15) . . ? C1 N2 C4 123.1(2) . . ? C1 N2 C17 121.87(19) . . ? C17 N2 C4 115.02(18) . . ? C29 N3 C30 128.94(19) . . ? C29 N3 C34 113.96(18) . . ? C34 N3 C30 117.10(18) . . ? C34 N4 C35 118.78(19) . . ? C34 N4 B1 113.30(18) . . ? C35 N4 B1 127.86(19) . . ? N1 C1 Cu1 117.85(16) . . ? N2 C1 Cu1 125.70(16) . . ? N2 C1 N1 116.4(2) . . ? C3 C2 N1 112.0(2) . . ? C2 C3 C4 110.1(3) . . ? N2 C4 C3 109.4(2) . . ? C18 C17 N2 118.1(2) . . ? C18 C17 C22 122.2(2) . . ? C22 C17 N2 119.5(2) . . ? C17 C18 C23 122.7(2) . . ? C19 C18 C17 117.3(2) . . ? C19 C18 C23 120.0(2) . . ? C20 C19 C18 121.7(3) . . ? C21 C20 C19 120.3(3) . . ? C20 C21 C22 121.1(3) . . ? C17 C22 C26 122.8(2) . . ? C21 C22 C17 117.5(2) . . ? C21 C22 C26 119.7(2) . . ? C18 C23 C24 112.2(2) . . ? C18 C23 C25 112.3(3) . . ? C25 C23 C24 108.8(3) . . ? C22 C26 C27 110.6(2) . . ? C22 C26 C28 112.0(2) . . ? C28 C26 C27 110.9(2) . . ? N3 C29 Cu1 127.92(16) . . ? N3 C29 B1 106.83(18) . . ? B1 C29 Cu1 125.19(15) . . ? N3 C30 C32 109.0(2) . . ? N3 C30 C33 108.9(2) . . ? C31 C30 N3 109.9(2) . . ? C31 C30 C32 108.5(2) . . ? C31 C30 C33 108.4(2) . . ? C33 C30 C32 112.1(2) . . ? O1 C34 N3 121.9(2) . . ? O1 C34 N4 130.3(2) . . ? N4 C34 N3 107.73(19) . . ? C36 C35 N4 120.4(2) . . ? C36 C35 C40 119.5(2) . . ? C40 C35 N4 120.0(2) . . ? C37 C36 C35 120.3(3) . . ? C38 C37 C36 120.1(3) . . ? C37 C38 C39 120.0(3) . . ? C38 C39 C40 119.9(3) . . ? C35 C40 C39 120.2(2) . . ? O2 C41 C42 109.1(2) . . ? O2 C41 C43 109.5(2) . . ? O2 C41 C44 102.76(18) . . ? C42 C41 C43 108.7(2) . . ? C42 C41 C44 114.4(2) . . ? C43 C41 C44 112.1(2) . . ? O3 C44 C41 102.82(18) . . ? O3 C44 C45 108.2(2) . . ? O3 C44 C46 108.2(2) . . ? C45 C44 C41 112.8(2) . . ? C46 C44 C41 115.5(2) . . ? C46 C44 C45 108.9(2) . . ? C6 C5 N1 118.6(4) . . ? C10 C5 N1 120.6(4) . . ? C10 C5 C6 120.7(4) . . ? C5 C6 C11 123.0(5) . . ? C7 C6 C5 118.9(5) . . ? C7 C6 C11 117.9(4) . . ? C6 C7 C8 120.6(5) . . ? C9 C8 C7 120.3(5) . . ? C8 C9 C10 119.8(5) . . ? C5 C10 C14 123.1(4) . . ? C9 C10 C5 119.6(5) . . ? C9 C10 C14 117.3(5) . . ? C6 C11 C12 110.8(6) . . ? C6 C11 C13 115.7(5) . . ? C13 C11 C12 107.3(5) . . ? C10 C14 C15 111.7(5) . . ? C10 C14 C16 114.8(5) . . ? C16 C14 C15 107.0(6) . . ? C6A C5A N1 118.5(7) . . ? C10A C5A N1 115.8(7) . . ? C10A C5A C6A 125.7(7) . . ? C5A C6A C11A 122.5(9) . . ? C7A C6A C5A 116.9(9) . . ? C7A C6A C11A 120.6(9) . . ? C8A C7A C6A 118.6(9) . . ? C7A C8A C9A 122.9(10) . . ? C10A C9A C8A 120.0(9) . . ? C5A C10A C14A 125.9(8) . . ? C9A C10A C5A 115.6(8) . . ? C9A C10A C14A 118.5(7) . . ? C6A C11A C12A 108.8(13) . . ? C6A C11A C13A 113.4(10) . . ? C13A C11A C12A 108.3(10) . . ? C10A C14A C15A 110.5(9) . . ? C10A C14A C16A 114.7(9) . . ? C16A C14A C15A 109.2(10) . . ? O2 B1 O3 107.02(19) . . ? O2 B1 N4 114.82(19) . . ? O2 B1 C29 115.83(19) . . ? O3 B1 N4 109.46(19) . . ? O3 B1 C29 111.93(18) . . ? N4 B1 C29 97.61(17) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.955(2) . ? Cu1 C29 1.925(2) . ? O1 C34 1.209(3) . ? O2 C41 1.430(3) . ? O2 B1 1.439(3) . ? O3 C44 1.426(3) . ? O3 B1 1.454(3) . ? N1 C1 1.350(3) . ? N1 C2 1.479(3) . ? N1 C5 1.454(4) . ? N1 C5A 1.452(5) . ? N2 C1 1.335(3) . ? N2 C4 1.477(3) . ? N2 C17 1.449(3) . ? N3 C29 1.314(3) . ? N3 C30 1.509(3) . ? N3 C34 1.493(3) . ? N4 C34 1.315(3) . ? N4 C35 1.422(3) . ? N4 B1 1.574(3) . ? C2 C3 1.468(4) . ? C3 C4 1.502(4) . ? C17 C18 1.400(3) . ? C17 C22 1.403(3) . ? C18 C19 1.392(4) . ? C18 C23 1.523(4) . ? C19 C20 1.373(4) . ? C20 C21 1.371(4) . ? C21 C22 1.399(4) . ? C22 C26 1.513(3) . ? C23 C24 1.533(4) . ? C23 C25 1.523(4) . ? C26 C27 1.537(4) . ? C26 C28 1.529(4) . ? C29 B1 1.656(3) . ? C30 C31 1.507(4) . ? C30 C32 1.534(4) . ? C30 C33 1.517(4) . ? C35 C36 1.382(3) . ? C35 C40 1.382(3) . ? C36 C37 1.380(4) . ? C37 C38 1.377(4) . ? C38 C39 1.379(4) . ? C39 C40 1.385(3) . ? C41 C42 1.516(4) . ? C41 C43 1.531(4) . ? C41 C44 1.556(4) . ? C44 C45 1.527(4) . ? C44 C46 1.522(4) . ? C5 C6 1.396(4) . ? C5 C10 1.395(4) . ? C6 C7 1.388(4) . ? C6 C11 1.515(5) . ? C7 C8 1.390(4) . ? C8 C9 1.387(4) . ? C9 C10 1.392(4) . ? C10 C14 1.516(5) . ? C11 C12 1.532(4) . ? C11 C13 1.530(4) . ? C14 C15 1.538(4) . ? C14 C16 1.536(4) . ? C5A C6A 1.392(4) . ? C5A C10A 1.391(4) . ? C6A C7A 1.390(4) . ? C6A C11A 1.515(6) . ? C7A C8A 1.388(4) . ? C8A C9A 1.389(4) . ? C9A C10A 1.389(4) . ? C10A C14A 1.515(6) . ? C11A C12A 1.534(4) . ? C11A C13A 1.533(4) . ? C14A C15A 1.536(4) . ? C14A C16A 1.533(4) . ?