#------------------------------------------------------------------------------ #$Date: 2019-11-17 04:50:51 +0200 (Sun, 17 Nov 2019) $ #$Revision: 227957 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/00/1550035.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_1550035 loop_ _publ_author_name 'Zelenay, Benjamin' 'Besora, Maria' 'Monasterio, Zaira' 'Ventura-Espinosa, David' 'White, Andrew J. P.' 'Maseras, Feliu' 'D\'iez-Gonz\'alez, Silvia' _publ_section_title ; Copper-mediated reduction of azides under seemingly oxidising conditions: catalytic and computational studies ; _journal_issue 22 _journal_name_full 'Catalysis Science & Technology' _journal_page_first 5763 _journal_paper_doi 10.1039/C8CY00515J _journal_volume 8 _journal_year 2018 _chemical_formula_moiety 'C36 H44 Cu N4, C F3 O3 S' _chemical_formula_sum 'C37 H44 Cu F3 N4 O3 S' _chemical_formula_weight 745.36 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-11-03 deposited with the CCDC. 2018-08-30 downloaded from the CCDC. ; _cell_angle_alpha 89.693(4) _cell_angle_beta 79.192(4) _cell_angle_gamma 82.793(4) _cell_formula_units_Z 2 _cell_length_a 9.1002(5) _cell_length_b 10.9858(6) _cell_length_c 19.3481(7) _cell_measurement_reflns_used 2893 _cell_measurement_temperature 233(2) _cell_measurement_theta_max 26.5060 _cell_measurement_theta_min 2.5220 _cell_volume 1884.64(16) _computing_cell_refinement 'CrysAlisPro, Agilent Technologies' _computing_data_collection 'CrysAlisPro, Agilent Technologies' _computing_data_reduction 'CrysAlisPro, Agilent Technologies' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CIFTAB-2014 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 233(2) _diffrn_detector_area_resol_mean 16.0382 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.799 _diffrn_measurement_device_type 'Agilent Xcalibur 3 E' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_unetI/netI 0.0502 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.799 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 10872 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.799 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.199 _diffrn_reflns_theta_min 2.712 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.689 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_correction_T_min 0.794 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Red-brown _exptl_crystal_density_diffrn 1.313 _exptl_crystal_description blocks _exptl_crystal_F_000 780 _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.639 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 483 _refine_ls_number_reflns 7408 _refine_ls_number_restraints 139 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.0703 _refine_ls_R_factor_gt 0.0504 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+0.9974P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1138 _refine_ls_wR_factor_ref 0.1271 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5713 _reflns_number_total 7408 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8cy00515j2.cif _cod_data_source_block 8 _cod_depositor_comments 'Adding full bibliography for 1550033--1550035.cif.' _cod_database_code 1550035 _shelx_shelxl_version_number 2014/7 _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. ; _shelx_res_file ; SDG1517.res created by SHELXL-2014/7 TITL SDG1517 in P-1 REM P-1 (#2 in standard setting) REM BZ-452-2 CELL 0.71073 9.100243 10.985759 19.348071 89.6928 79.1925 82.7930 ZERR 2.00 0.000491 0.000565 0.000717 0.0037 0.0038 0.0044 LATT 1 SFAC C H Cu F N O S UNIT 74 88 2 6 8 6 2 TEMP -40 L.S. 6 OMIT 1 0 0 OMIT 1 0 1 FMAP 2 PLAN 10 ACTA REM 'C36 H44 Cu N4, C F3 O3 S' REM C37 H44 Cu F3 N4 O3 S SADI S50 C50 S50' C50' SADI S50 O51 S50 O52 S50 O53 S50' O51' S50' O52' S50' O53' SADI C50 F51 C50 F52 C50 F53 C50' F51' C50' F52' C50' F53' SADI O51 O52 O51 O53 O52 O53 O51' O52' O51' O53' O52' O53' SADI F51 F52 F51 F53 F52 F53 F51' F52' F51' F53' F52' F53' SADI S50 F51 S50 F52 S50 F53 S50' F51' S50' F52' S50' F53' SADI C50 O51 C50 O52 C50 O53 C50' O51' C50' O52' C50' O53' SIMU 0.02 0.02 1 S50 > F53' WGHT 0.051000 0.997400 FVAR 5.01572 0.75449 CU1 3 0.562276 0.766826 0.283571 11.00000 0.05547 0.02973 = 0.04595 0.00790 -0.00758 -0.01255 N1 5 0.375301 0.755826 0.360121 11.00000 0.05109 0.02720 = 0.03655 0.00054 -0.00616 -0.00423 C2 1 0.284072 0.843215 0.400479 11.00000 0.06827 0.02878 = 0.04995 -0.00473 -0.00793 -0.00235 AFIX 43 H2A 2 0.301124 0.925322 0.393078 11.00000 -1.20000 AFIX 0 C3 1 0.166893 0.818850 0.452117 11.00000 0.05831 0.04361 = 0.04274 -0.01266 -0.00431 0.00612 AFIX 43 H3A 2 0.105156 0.883230 0.479156 11.00000 -1.20000 AFIX 0 C4 1 0.140559 0.699896 0.463966 11.00000 0.05296 0.05332 = 0.04254 -0.00200 0.00122 -0.00320 AFIX 43 H4A 2 0.061150 0.681220 0.499371 11.00000 -1.20000 AFIX 0 C5 1 0.232855 0.607972 0.422925 11.00000 0.05265 0.03620 = 0.04540 0.00097 -0.00070 -0.00532 AFIX 43 H5A 2 0.217048 0.525444 0.429533 11.00000 -1.20000 AFIX 0 C6 1 0.348690 0.639427 0.372046 11.00000 0.04255 0.02845 = 0.03259 0.00047 -0.00729 -0.00476 C7 1 0.451843 0.547975 0.326160 11.00000 0.04466 0.02436 = 0.04042 -0.00034 -0.00553 -0.00440 AFIX 43 H7A 2 0.438532 0.464514 0.329336 11.00000 -1.20000 AFIX 0 N8 5 0.559954 0.582717 0.281834 11.00000 0.03706 0.02521 = 0.03567 0.00046 -0.00603 -0.00261 C9 1 0.658938 0.492405 0.236805 11.00000 0.03911 0.02651 = 0.04265 0.00216 0.00144 -0.00640 C10 1 0.608528 0.434192 0.183754 11.00000 0.04763 0.03782 = 0.04486 -0.00694 0.00250 -0.00797 C11 1 0.713874 0.349977 0.140505 11.00000 0.06806 0.04874 = 0.05748 -0.01412 0.00556 -0.00988 AFIX 43 H11A 2 0.684329 0.309942 0.103500 11.00000 -1.20000 AFIX 0 C12 1 0.858058 0.325012 0.151014 11.00000 0.05388 0.04491 = 0.08263 -0.01386 0.02020 0.00139 AFIX 43 H12A 2 0.925901 0.266626 0.121922 11.00000 -1.20000 AFIX 0 C13 1 0.905605 0.383406 0.203104 11.00000 0.04315 0.04395 = 0.09100 0.00363 0.00283 -0.00190 AFIX 43 H13A 2 1.005684 0.364511 0.209603 11.00000 -1.20000 AFIX 0 C14 1 0.808506 0.470268 0.246642 11.00000 0.04465 0.03336 = 0.06043 0.00864 -0.00634 -0.00601 C15 1 0.448202 0.460697 0.169967 11.00000 0.05352 0.06100 = 0.05034 -0.01951 -0.00949 -0.00823 AFIX 13 H15A 2 0.390129 0.519995 0.206431 11.00000 -1.20000 AFIX 0 C16 1 0.446604 0.518277 0.098521 11.00000 0.09747 0.12047 = 0.11273 0.03627 -0.05019 -0.03689 AFIX 137 H16A 2 0.484192 0.597165 0.097870 11.00000 -1.50000 H16B 2 0.344240 0.529640 0.089835 11.00000 -1.50000 H16C 2 0.510358 0.464796 0.062232 11.00000 -1.50000 AFIX 0 C17 1 0.372238 0.345425 0.175458 11.00000 0.07296 0.09059 = 0.08958 -0.00930 -0.00393 -0.03763 AFIX 137 H17A 2 0.431791 0.283546 0.142700 11.00000 -1.50000 H17B 2 0.272437 0.363732 0.164181 11.00000 -1.50000 H17C 2 0.363722 0.315002 0.223017 11.00000 -1.50000 AFIX 0 C18 1 0.860358 0.537745 0.303858 11.00000 0.05078 0.04296 = 0.07906 0.00449 -0.02560 -0.00190 AFIX 13 H18A 2 0.791645 0.615435 0.314082 11.00000 -1.20000 AFIX 0 C19 1 0.848717 0.466800 0.371501 11.00000 0.08802 0.09511 = 0.07197 0.00676 -0.01856 -0.02898 AFIX 137 H19A 2 0.744843 0.452920 0.387948 11.00000 -1.50000 H19B 2 0.881691 0.513466 0.406883 11.00000 -1.50000 H19C 2 0.912153 0.388532 0.363038 11.00000 -1.50000 AFIX 0 C20 1 1.018409 0.571369 0.281114 11.00000 0.08931 0.10638 = 0.10443 0.03021 -0.03887 -0.05395 AFIX 137 H20B 2 1.035979 0.632951 0.313334 11.00000 -1.50000 H20C 2 1.029445 0.603820 0.233954 11.00000 -1.50000 H20A 2 1.091047 0.498875 0.281487 11.00000 -1.50000 AFIX 0 N21 5 0.700631 0.879724 0.316602 11.00000 0.05025 0.03696 = 0.03796 0.00092 -0.01300 -0.00493 C22 1 0.758455 0.878028 0.374581 11.00000 0.07841 0.05148 = 0.04614 -0.00373 -0.02588 -0.00009 AFIX 43 H22A 2 0.751876 0.808913 0.403316 11.00000 -1.20000 AFIX 0 C23 1 0.827650 0.972712 0.394660 11.00000 0.07878 0.06569 = 0.05831 -0.01710 -0.03594 0.00271 AFIX 43 H23A 2 0.868507 0.967508 0.435899 11.00000 -1.20000 AFIX 0 C24 1 0.836281 1.074414 0.353943 11.00000 0.06562 0.06124 = 0.06919 -0.01851 -0.02146 -0.01951 AFIX 43 H24A 2 0.882934 1.140224 0.366818 11.00000 -1.20000 AFIX 0 C25 1 0.775992 1.079179 0.294067 11.00000 0.06020 0.04637 = 0.05578 -0.00032 -0.01212 -0.02281 AFIX 43 H25A 2 0.779879 1.148415 0.265338 11.00000 -1.20000 AFIX 0 C26 1 0.709417 0.980254 0.276774 11.00000 0.03814 0.03609 = 0.03804 0.00092 -0.00239 -0.00987 C27 1 0.646143 0.975164 0.213305 11.00000 0.04632 0.03569 = 0.04238 0.00957 -0.00994 -0.01394 AFIX 43 H27A 2 0.652422 1.039539 0.181105 11.00000 -1.20000 AFIX 0 N28 5 0.582225 0.882695 0.201826 11.00000 0.03656 0.03307 = 0.03297 0.00399 -0.00636 -0.00895 C29 1 0.535058 0.872289 0.135442 11.00000 0.04655 0.03549 = 0.03392 0.00746 -0.01125 -0.01497 C30 1 0.641312 0.823479 0.077668 11.00000 0.05051 0.04818 = 0.03794 0.00661 -0.00720 -0.01207 C31 1 0.592649 0.814048 0.014327 11.00000 0.06927 0.06240 = 0.03856 -0.00068 -0.00748 -0.01620 AFIX 43 H31A 2 0.661865 0.781941 -0.025638 11.00000 -1.20000 AFIX 0 C32 1 0.446260 0.850457 0.008866 11.00000 0.07359 0.06858 = 0.04606 0.00292 -0.02657 -0.02188 AFIX 43 H32A 2 0.416212 0.845085 -0.034810 11.00000 -1.20000 AFIX 0 C33 1 0.343251 0.894745 0.066872 11.00000 0.05378 0.05792 = 0.06195 0.00497 -0.02869 -0.01478 AFIX 43 H33A 2 0.242467 0.917986 0.062503 11.00000 -1.20000 AFIX 0 C34 1 0.383668 0.906249 0.131978 11.00000 0.04601 0.03950 = 0.04859 0.00153 -0.01427 -0.01334 C35 1 0.805093 0.780601 0.082404 11.00000 0.05191 0.08532 = 0.04274 -0.00295 -0.00619 -0.00184 AFIX 13 H35A 2 0.812797 0.780894 0.132766 11.00000 -1.20000 AFIX 0 C36 1 0.857972 0.650471 0.053246 11.00000 0.06990 0.08128 = 0.11244 0.00458 0.00518 0.00564 AFIX 137 H36B 2 0.958801 0.624434 0.061737 11.00000 -1.50000 H36C 2 0.859022 0.648908 0.003033 11.00000 -1.50000 H36A 2 0.789714 0.595338 0.076429 11.00000 -1.50000 AFIX 0 C37 1 0.907599 0.867747 0.045435 11.00000 0.06044 0.10016 = 0.12549 0.00255 -0.01773 -0.02847 AFIX 137 H37B 2 1.010353 0.840968 0.050999 11.00000 -1.50000 H37A 2 0.875829 0.949548 0.065695 11.00000 -1.50000 H37C 2 0.902686 0.868894 -0.004218 11.00000 -1.50000 AFIX 0 C38 1 0.267978 0.950828 0.195868 11.00000 0.04162 0.05827 = 0.05959 -0.00347 -0.01262 -0.00705 AFIX 13 H38A 2 0.322266 0.968294 0.233779 11.00000 -1.20000 AFIX 0 C39 1 0.169164 1.068265 0.182898 11.00000 0.07464 0.05248 = 0.11454 0.00331 0.00613 -0.00287 AFIX 137 H39A 2 0.232192 1.126577 0.159133 11.00000 -1.50000 H39B 2 0.113732 1.103397 0.227543 11.00000 -1.50000 H39C 2 0.098722 1.049511 0.153768 11.00000 -1.50000 AFIX 0 C40 1 0.168764 0.851475 0.221416 11.00000 0.06842 0.06401 = 0.08330 0.01337 0.00322 -0.01188 AFIX 137 H40A 2 0.113172 0.833555 0.185336 11.00000 -1.50000 H40B 2 0.098465 0.879938 0.264004 11.00000 -1.50000 H40C 2 0.231540 0.777728 0.231160 11.00000 -1.50000 AFIX 0 PART 1 S50 7 0.279653 0.199572 0.385683 21.00000 0.05132 0.02342 = 0.06310 -0.00057 0.00933 0.00068 O51 6 0.164577 0.143578 0.430795 21.00000 0.06648 0.04832 = 0.10843 0.00319 0.04203 -0.00971 O52 6 0.374197 0.115711 0.331943 21.00000 0.10109 0.04614 = 0.07514 -0.01381 0.01961 -0.00522 O53 6 0.235648 0.318624 0.359326 21.00000 0.07943 0.03103 = 0.08999 0.00750 -0.01104 0.00943 C50 1 0.414973 0.225797 0.438694 21.00000 0.09160 0.06154 = 0.10171 0.03420 0.00309 0.00935 F51 4 0.530037 0.280234 0.405710 21.00000 0.07717 0.08588 = 0.09892 0.01272 -0.02608 -0.02915 F52 4 0.343320 0.300978 0.494657 21.00000 0.19919 0.07854 = 0.08438 -0.01353 0.01035 -0.03448 F53 4 0.471365 0.122266 0.464486 21.00000 0.12173 0.08371 = 0.13692 0.05842 -0.02981 0.01993 PART 2 S50' 7 0.246059 0.219506 0.403909 -21.00000 0.07983 O51' 6 0.160670 0.147336 0.448800 -21.00000 0.06969 O52' 6 0.334681 0.137743 0.338289 -21.00000 0.07611 O53' 6 0.204909 0.333851 0.381306 -21.00000 0.06679 C50' 1 0.416769 0.232775 0.439004 -21.00000 0.05598 F51' 4 0.523933 0.260618 0.384617 -21.00000 0.07548 F52' 4 0.380666 0.323435 0.486324 -21.00000 0.07156 F53' 4 0.465559 0.131034 0.468240 -21.00000 0.09489 PART 0 HKLF 4 REM SDG1517 in P-1 REM R1 = 0.0504 for 5713 Fo > 4sig(Fo) and 0.0703 for all 7408 data REM 483 parameters refined using 139 restraints END WGHT 0.0510 0.9998 REM Highest difference peak 0.639, deepest hole -0.411, 1-sigma level 0.053 Q1 1 0.2064 0.3071 0.4772 11.00000 0.05 0.64 Q2 1 0.4092 0.1701 0.3811 11.00000 0.05 0.39 Q3 1 0.4059 0.5841 0.1494 11.00000 0.05 0.38 Q4 1 0.2117 0.2576 0.4267 11.00000 0.05 0.36 Q5 1 0.4738 0.0928 0.4128 11.00000 0.05 0.35 Q6 1 0.5179 0.2463 0.3548 11.00000 0.05 0.30 Q7 1 0.4915 0.1125 0.3608 11.00000 0.05 0.29 Q8 1 0.2681 0.2433 0.3507 11.00000 0.05 0.27 Q9 1 0.6745 0.7438 0.2592 11.00000 0.05 0.26 Q10 1 0.5455 0.4633 0.1580 11.00000 0.05 0.25 ; _shelx_res_checksum 63086 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 0.56228(4) 0.76683(3) 0.28357(2) 0.04338(13) Uani 1 1 d . . . . . N1 N 0.3753(3) 0.7558(2) 0.36012(11) 0.0386(5) Uani 1 1 d . . . . . C2 C 0.2841(4) 0.8432(3) 0.40048(16) 0.0497(8) Uani 1 1 d . . . . . H2A H 0.3011 0.9253 0.3931 0.060 Uiso 1 1 calc R U . . . C3 C 0.1669(4) 0.8189(3) 0.45212(15) 0.0499(8) Uani 1 1 d . . . . . H3A H 0.1052 0.8832 0.4792 0.060 Uiso 1 1 calc R U . . . C4 C 0.1406(4) 0.6999(3) 0.46397(15) 0.0512(8) Uani 1 1 d . . . . . H4A H 0.0612 0.6812 0.4994 0.061 Uiso 1 1 calc R U . . . C5 C 0.2329(3) 0.6080(3) 0.42292(15) 0.0459(7) Uani 1 1 d . . . . . H5A H 0.2170 0.5254 0.4295 0.055 Uiso 1 1 calc R U . . . C6 C 0.3487(3) 0.6394(2) 0.37205(13) 0.0345(6) Uani 1 1 d . . . . . C7 C 0.4518(3) 0.5480(2) 0.32616(13) 0.0368(6) Uani 1 1 d . . . . . H7A H 0.4385 0.4645 0.3293 0.044 Uiso 1 1 calc R U . . . N8 N 0.5600(2) 0.58272(19) 0.28183(11) 0.0329(5) Uani 1 1 d . . . . . C9 C 0.6589(3) 0.4924(2) 0.23680(14) 0.0371(6) Uani 1 1 d . . . . . C10 C 0.6085(3) 0.4342(3) 0.18375(15) 0.0447(7) Uani 1 1 d . . . . . C11 C 0.7139(4) 0.3500(3) 0.14050(18) 0.0601(9) Uani 1 1 d . . . . . H11A H 0.6843 0.3099 0.1035 0.072 Uiso 1 1 calc R U . . . C12 C 0.8581(4) 0.3250(3) 0.1510(2) 0.0654(10) Uani 1 1 d . . . . . H12A H 0.9259 0.2666 0.1219 0.078 Uiso 1 1 calc R U . . . C13 C 0.9056(4) 0.3834(3) 0.2031(2) 0.0617(9) Uani 1 1 d . . . . . H13A H 1.0057 0.3645 0.2096 0.074 Uiso 1 1 calc R U . . . C14 C 0.8085(3) 0.4703(3) 0.24664(16) 0.0465(7) Uani 1 1 d . . . . . C15 C 0.4482(4) 0.4607(3) 0.16997(16) 0.0548(8) Uani 1 1 d . . . . . H15A H 0.3901 0.5200 0.2064 0.066 Uiso 1 1 calc R U . . . C16 C 0.4466(6) 0.5183(5) 0.0985(3) 0.1044(16) Uani 1 1 d . . . . . H16A H 0.4842 0.5972 0.0979 0.157 Uiso 1 1 calc R U . . . H16B H 0.3442 0.5296 0.0898 0.157 Uiso 1 1 calc R U . . . H16C H 0.5104 0.4648 0.0622 0.157 Uiso 1 1 calc R U . . . C17 C 0.3722(5) 0.3454(4) 0.1755(2) 0.0835(13) Uani 1 1 d . . . . . H17A H 0.4318 0.2835 0.1427 0.125 Uiso 1 1 calc R U . . . H17B H 0.2724 0.3637 0.1642 0.125 Uiso 1 1 calc R U . . . H17C H 0.3637 0.3150 0.2230 0.125 Uiso 1 1 calc R U . . . C18 C 0.8604(4) 0.5377(3) 0.30386(19) 0.0562(8) Uani 1 1 d . . . . . H18A H 0.7916 0.6154 0.3141 0.067 Uiso 1 1 calc R U . . . C19 C 0.8487(5) 0.4668(4) 0.3715(2) 0.0831(12) Uani 1 1 d . . . . . H19A H 0.7448 0.4529 0.3879 0.125 Uiso 1 1 calc R U . . . H19B H 0.8817 0.5135 0.4069 0.125 Uiso 1 1 calc R U . . . H19C H 0.9122 0.3885 0.3630 0.125 Uiso 1 1 calc R U . . . C20 C 1.0184(5) 0.5714(5) 0.2811(2) 0.0939(15) Uani 1 1 d . . . . . H20B H 1.0360 0.6330 0.3133 0.141 Uiso 1 1 calc R U . . . H20C H 1.0294 0.6038 0.2340 0.141 Uiso 1 1 calc R U . . . H20A H 1.0910 0.4989 0.2815 0.141 Uiso 1 1 calc R U . . . N21 N 0.7006(3) 0.8797(2) 0.31660(11) 0.0412(6) Uani 1 1 d . . . . . C22 C 0.7585(4) 0.8780(3) 0.37458(16) 0.0575(9) Uani 1 1 d . . . . . H22A H 0.7519 0.8089 0.4033 0.069 Uiso 1 1 calc R U . . . C23 C 0.8277(4) 0.9727(4) 0.39466(19) 0.0655(10) Uani 1 1 d . . . . . H23A H 0.8685 0.9675 0.4359 0.079 Uiso 1 1 calc R U . . . C24 C 0.8363(4) 1.0744(4) 0.35394(19) 0.0631(10) Uani 1 1 d . . . . . H24A H 0.8829 1.1402 0.3668 0.076 Uiso 1 1 calc R U . . . C25 C 0.7760(4) 1.0792(3) 0.29407(17) 0.0526(8) Uani 1 1 d . . . . . H25A H 0.7799 1.1484 0.2653 0.063 Uiso 1 1 calc R U . . . C26 C 0.7094(3) 0.9803(3) 0.27677(14) 0.0376(6) Uani 1 1 d . . . . . C27 C 0.6461(3) 0.9752(3) 0.21330(14) 0.0405(7) Uani 1 1 d . . . . . H27A H 0.6524 1.0395 0.1811 0.049 Uiso 1 1 calc R U . . . N28 N 0.5822(2) 0.8827(2) 0.20183(11) 0.0338(5) Uani 1 1 d . . . . . C29 C 0.5351(3) 0.8723(3) 0.13544(13) 0.0374(6) Uani 1 1 d . . . . . C30 C 0.6413(3) 0.8235(3) 0.07767(14) 0.0452(7) Uani 1 1 d . . . . . C31 C 0.5926(4) 0.8140(3) 0.01433(16) 0.0564(9) Uani 1 1 d . . . . . H31A H 0.6619 0.7819 -0.0256 0.068 Uiso 1 1 calc R U . . . C32 C 0.4463(4) 0.8505(3) 0.00887(17) 0.0596(9) Uani 1 1 d . . . . . H32A H 0.4162 0.8451 -0.0348 0.072 Uiso 1 1 calc R U . . . C33 C 0.3433(4) 0.8947(3) 0.06687(17) 0.0549(8) Uani 1 1 d . . . . . H33A H 0.2425 0.9180 0.0625 0.066 Uiso 1 1 calc R U . . . C34 C 0.3837(3) 0.9062(3) 0.13198(15) 0.0433(7) Uani 1 1 d . . . . . C35 C 0.8051(4) 0.7806(4) 0.08240(17) 0.0609(9) Uani 1 1 d . . . . . H35A H 0.8128 0.7809 0.1328 0.073 Uiso 1 1 calc R U . . . C36 C 0.8580(5) 0.6505(4) 0.0532(3) 0.0921(14) Uani 1 1 d . . . . . H36B H 0.9588 0.6244 0.0617 0.138 Uiso 1 1 calc R U . . . H36C H 0.8590 0.6489 0.0030 0.138 Uiso 1 1 calc R U . . . H36A H 0.7897 0.5953 0.0764 0.138 Uiso 1 1 calc R U . . . C37 C 0.9076(5) 0.8677(4) 0.0454(3) 0.0938(14) Uani 1 1 d . . . . . H37B H 1.0104 0.8410 0.0510 0.141 Uiso 1 1 calc R U . . . H37A H 0.8758 0.9495 0.0657 0.141 Uiso 1 1 calc R U . . . H37C H 0.9027 0.8689 -0.0042 0.141 Uiso 1 1 calc R U . . . C38 C 0.2680(3) 0.9508(3) 0.19587(17) 0.0527(8) Uani 1 1 d . . . . . H38A H 0.3223 0.9683 0.2338 0.063 Uiso 1 1 calc R U . . . C39 C 0.1692(5) 1.0683(4) 0.1829(2) 0.0841(12) Uani 1 1 d . . . . . H39A H 0.2322 1.1266 0.1591 0.126 Uiso 1 1 calc R U . . . H39B H 0.1137 1.1034 0.2275 0.126 Uiso 1 1 calc R U . . . H39C H 0.0987 1.0495 0.1538 0.126 Uiso 1 1 calc R U . . . C40 C 0.1688(4) 0.8515(4) 0.2214(2) 0.0739(11) Uani 1 1 d . . . . . H40A H 0.1132 0.8336 0.1853 0.111 Uiso 1 1 calc R U . . . H40B H 0.0985 0.8799 0.2640 0.111 Uiso 1 1 calc R U . . . H40C H 0.2315 0.7777 0.2312 0.111 Uiso 1 1 calc R U . . . S50 S 0.2797(3) 0.19957(14) 0.38568(16) 0.0490(6) Uani 0.754(13) 1 d D U P A 1 O51 O 0.1646(7) 0.1436(5) 0.4308(4) 0.082(2) Uani 0.754(13) 1 d D U P A 1 O52 O 0.3742(8) 0.1157(5) 0.3319(3) 0.0792(16) Uani 0.754(13) 1 d D U P A 1 O53 O 0.2356(6) 0.3186(3) 0.3593(4) 0.0689(13) Uani 0.754(13) 1 d D U P A 1 C50 C 0.4150(8) 0.2258(7) 0.4387(4) 0.089(4) Uani 0.754(13) 1 d D U P A 1 F51 F 0.5300(5) 0.2802(5) 0.4057(4) 0.0845(14) Uani 0.754(13) 1 d D U P A 1 F52 F 0.3433(9) 0.3010(5) 0.4947(3) 0.124(2) Uani 0.754(13) 1 d D U P A 1 F53 F 0.4714(9) 0.1223(6) 0.4645(4) 0.116(3) Uani 0.754(13) 1 d D U P A 1 S50' S 0.2461(12) 0.2195(11) 0.4039(6) 0.080(2) Uiso 0.246(13) 1 d D U P A 2 O51' O 0.161(2) 0.1473(19) 0.4488(10) 0.070(5) Uiso 0.246(13) 1 d D U P A 2 O52' O 0.335(2) 0.1377(17) 0.3383(8) 0.076(5) Uiso 0.246(13) 1 d D U P A 2 O53' O 0.2049(19) 0.3339(13) 0.3813(8) 0.067(5) Uiso 0.246(13) 1 d D U P A 2 C50' C 0.4168(15) 0.2328(14) 0.4390(7) 0.056(7) Uiso 0.246(13) 1 d D U P A 2 F51' F 0.5239(15) 0.2606(16) 0.3846(7) 0.075(5) Uiso 0.246(13) 1 d D U P A 2 F52' F 0.3807(16) 0.3234(15) 0.4863(7) 0.072(4) Uiso 0.246(13) 1 d D U P A 2 F53' F 0.466(2) 0.1310(15) 0.4682(11) 0.095(7) Uiso 0.246(13) 1 d D U P A 2 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 0.0555(2) 0.0297(2) 0.0460(2) 0.00790(15) -0.00758(17) -0.01255(16) N1 0.0511(14) 0.0272(12) 0.0366(12) 0.0005(9) -0.0062(11) -0.0042(11) C2 0.068(2) 0.0288(16) 0.0500(17) -0.0047(13) -0.0079(16) -0.0024(15) C3 0.0583(19) 0.0436(19) 0.0427(16) -0.0127(14) -0.0043(15) 0.0061(15) C4 0.0530(19) 0.053(2) 0.0425(16) -0.0020(14) 0.0012(14) -0.0032(16) C5 0.0526(18) 0.0362(17) 0.0454(16) 0.0010(13) -0.0007(14) -0.0053(14) C6 0.0426(15) 0.0285(14) 0.0326(13) 0.0005(11) -0.0073(12) -0.0048(12) C7 0.0447(16) 0.0244(14) 0.0404(14) -0.0003(11) -0.0055(13) -0.0044(12) N8 0.0371(12) 0.0252(11) 0.0357(11) 0.0005(9) -0.0060(10) -0.0026(9) C9 0.0391(15) 0.0265(14) 0.0427(14) 0.0022(11) 0.0014(12) -0.0064(12) C10 0.0476(17) 0.0378(17) 0.0449(15) -0.0069(13) 0.0025(14) -0.0080(14) C11 0.068(2) 0.049(2) 0.0575(19) -0.0141(16) 0.0056(18) -0.0099(18) C12 0.054(2) 0.045(2) 0.083(2) -0.0139(18) 0.0202(19) 0.0014(17) C13 0.0432(18) 0.044(2) 0.091(3) 0.0036(19) 0.0028(18) -0.0019(16) C14 0.0446(17) 0.0334(16) 0.0604(18) 0.0086(14) -0.0063(15) -0.0060(13) C15 0.0535(19) 0.061(2) 0.0503(18) -0.0195(16) -0.0095(15) -0.0082(16) C16 0.097(3) 0.120(4) 0.113(4) 0.036(3) -0.050(3) -0.037(3) C17 0.073(3) 0.091(3) 0.090(3) -0.009(2) -0.004(2) -0.038(2) C18 0.0508(19) 0.0430(19) 0.079(2) 0.0045(17) -0.0256(17) -0.0019(15) C19 0.088(3) 0.095(3) 0.072(2) 0.007(2) -0.019(2) -0.029(3) C20 0.089(3) 0.106(4) 0.104(3) 0.030(3) -0.039(3) -0.054(3) N21 0.0502(14) 0.0370(14) 0.0380(12) 0.0009(10) -0.0130(11) -0.0049(11) C22 0.078(2) 0.051(2) 0.0461(17) -0.0037(15) -0.0259(17) -0.0001(18) C23 0.079(2) 0.066(3) 0.058(2) -0.0171(19) -0.0359(19) 0.003(2) C24 0.066(2) 0.061(2) 0.069(2) -0.0185(19) -0.0215(19) -0.0195(19) C25 0.060(2) 0.0464(19) 0.0558(18) -0.0003(15) -0.0121(16) -0.0228(16) C26 0.0381(15) 0.0361(16) 0.0380(14) 0.0009(12) -0.0024(12) -0.0099(12) C27 0.0463(16) 0.0357(16) 0.0424(15) 0.0096(12) -0.0099(13) -0.0139(13) N28 0.0366(12) 0.0331(13) 0.0330(11) 0.0040(9) -0.0064(10) -0.0090(10) C29 0.0466(16) 0.0355(15) 0.0339(13) 0.0075(11) -0.0112(13) -0.0150(13) C30 0.0505(18) 0.0482(19) 0.0379(15) 0.0066(13) -0.0072(14) -0.0121(15) C31 0.069(2) 0.062(2) 0.0386(16) -0.0007(15) -0.0075(16) -0.0162(18) C32 0.074(2) 0.069(2) 0.0461(18) 0.0029(16) -0.0266(18) -0.0219(19) C33 0.0538(19) 0.058(2) 0.062(2) 0.0050(17) -0.0287(17) -0.0148(16) C34 0.0460(17) 0.0395(17) 0.0486(16) 0.0015(13) -0.0143(14) -0.0133(13) C35 0.052(2) 0.085(3) 0.0427(17) -0.0029(17) -0.0062(15) -0.0018(19) C36 0.070(3) 0.081(3) 0.112(3) 0.005(3) 0.005(3) 0.006(2) C37 0.060(2) 0.100(4) 0.125(4) 0.003(3) -0.018(3) -0.028(2) C38 0.0416(17) 0.058(2) 0.0596(19) -0.0035(16) -0.0126(15) -0.0070(15) C39 0.075(3) 0.052(2) 0.115(3) 0.003(2) 0.006(2) -0.003(2) C40 0.068(2) 0.064(3) 0.083(3) 0.013(2) 0.003(2) -0.012(2) S50 0.0513(9) 0.0234(8) 0.0631(10) -0.0006(6) 0.0093(8) 0.0007(5) O51 0.066(3) 0.048(2) 0.108(4) 0.003(3) 0.042(3) -0.0097(17) O52 0.101(4) 0.046(3) 0.075(3) -0.0138(18) 0.020(2) -0.005(2) O53 0.079(3) 0.0310(19) 0.090(4) 0.008(2) -0.011(3) 0.0094(17) C50 0.092(5) 0.062(4) 0.102(6) 0.034(4) 0.003(4) 0.009(3) F51 0.077(2) 0.086(3) 0.099(3) 0.013(3) -0.026(2) -0.0292(19) F52 0.199(6) 0.079(3) 0.084(3) -0.014(2) 0.010(3) -0.034(3) F53 0.122(4) 0.084(3) 0.137(4) 0.058(3) -0.030(3) 0.020(2) 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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 N28 Cu1 N8 128.58(8) N28 Cu1 N1 127.33(9) N8 Cu1 N1 80.98(9) N28 Cu1 N21 80.75(9) N8 Cu1 N21 134.02(9) N1 Cu1 N21 110.44(9) C2 N1 C6 117.1(2) C2 N1 Cu1 130.7(2) C6 N1 Cu1 112.06(18) N1 C2 C3 123.1(3) C4 C3 C2 119.4(3) C3 C4 C5 118.7(3) C6 C5 C4 118.7(3) N1 C6 C5 123.0(3) N1 C6 C7 114.6(2) C5 C6 C7 122.4(3) N8 C7 C6 119.2(2) C7 N8 C9 118.6(2) C7 N8 Cu1 112.99(18) C9 N8 Cu1 128.37(17) C10 C9 C14 122.2(3) C10 C9 N8 120.6(2) C14 C9 N8 117.2(2) C9 C10 C11 117.0(3) C9 C10 C15 123.2(3) C11 C10 C15 119.8(3) C12 C11 C10 121.2(3) C11 C12 C13 120.9(3) C12 C13 C14 120.9(3) C13 C14 C9 117.7(3) C13 C14 C18 121.6(3) C9 C14 C18 120.7(3) C17 C15 C16 110.4(3) C17 C15 C10 111.0(3) C16 C15 C10 111.1(3) C19 C18 C14 112.0(3) C19 C18 C20 110.3(3) C14 C18 C20 112.6(3) C22 N21 C26 117.5(3) C22 N21 Cu1 130.5(2) C26 N21 Cu1 110.98(17) N21 C22 C23 123.0(3) C24 C23 C22 119.2(3) C23 C24 C25 119.1(3) C24 C25 C26 118.7(3) N21 C26 C25 122.6(3) N21 C26 C27 114.6(2) C25 C26 C27 122.7(3) N28 C27 C26 119.3(2) C27 N28 C29 118.7(2) C27 N28 Cu1 112.68(18) C29 N28 Cu1 128.60(17) C30 C29 C34 122.5(2) C30 C29 N28 118.6(2) C34 C29 N28 118.9(2) C31 C30 C29 117.4(3) C31 C30 C35 120.2(3) C29 C30 C35 122.4(3) C32 C31 C30 121.3(3) C31 C32 C33 120.1(3) C32 C33 C34 121.7(3) C33 C34 C29 116.9(3) C33 C34 C38 121.1(3) C29 C34 C38 122.0(3) C37 C35 C30 110.8(3) C37 C35 C36 110.0(3) C30 C35 C36 112.6(3) C34 C38 C40 110.5(3) C34 C38 C39 112.9(3) C40 C38 C39 109.6(3) O51 S50 O53 116.8(3) O51 S50 O52 113.7(3) O53 S50 O52 113.5(3) O51 S50 C50 106.0(4) O53 S50 C50 104.4(3) O52 S50 C50 100.2(3) F53 C50 F51 107.6(6) F53 C50 F52 107.6(6) F51 C50 F52 106.8(6) F53 C50 S50 111.4(5) F51 C50 S50 114.7(5) F52 C50 S50 108.5(5) O53' S50' O51' 128.5(10) O53' S50' O52' 108.6(9) O51' S50' O52' 108.6(9) O53' S50' C50' 104.6(8) O51' S50' C50' 107.4(8) O52' S50' C50' 93.4(7) F53' C50' F52' 110.2(11) F53' C50' F51' 109.7(12) F52' C50' F51' 110.9(11) F53' C50' S50' 112.4(10) F52' C50' S50' 106.1(9) F51' C50' S50' 107.4(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cu1 N28 2.021(2) Cu1 N8 2.026(2) Cu1 N1 2.051(2) Cu1 N21 2.058(2) N1 C2 1.336(4) N1 C6 1.342(3) C2 C3 1.370(4) C3 C4 1.368(4) C4 C5 1.379(4) C5 C6 1.378(4) C6 C7 1.463(4) C7 N8 1.274(3) N8 C9 1.430(3) C9 C10 1.389(4) C9 C14 1.401(4) C10 C11 1.400(4) C10 C15 1.524(4) C11 C12 1.359(5) C12 C13 1.362(5) C13 C14 1.385(4) C14 C18 1.513(4) C15 C17 1.511(5) C15 C16 1.519(5) C18 C19 1.513(5) C18 C20 1.514(5) N21 C22 1.325(4) N21 C26 1.345(3) C22 C23 1.375(5) C23 C24 1.365(5) C24 C25 1.370(5) C25 C26 1.380(4) C26 C27 1.455(4) C27 N28 1.272(3) N28 C29 1.438(3) C29 C30 1.394(4) C29 C34 1.395(4) C30 C31 1.388(4) C30 C35 1.525(4) C31 C32 1.365(5) C32 C33 1.368(5) C33 C34 1.387(4) C34 C38 1.505(4) C35 C37 1.505(5) C35 C36 1.526(6) C38 C40 1.525(5) C38 C39 1.525(5) S50 O51 1.432(4) S50 O53 1.438(3) S50 O52 1.465(4) S50 C50 1.794(7) C50 F53 1.323(6) C50 F51 1.328(7) C50 F52 1.375(7) S50' O53' 1.359(10) S50' O51' 1.371(11) S50' O52' 1.586(11) S50' C50' 1.830(11) C50' F53' 1.315(12) C50' F52' 1.324(12) C50' F51' 1.356(12)