#------------------------------------------------------------------------------ #$Date: 2018-10-17 00:57:20 +0300 (Wed, 17 Oct 2018) $ #$Revision: 211474 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/00/1550034.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_1550034 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_name_full 'Catalysis Science & Technology' _journal_paper_doi 10.1039/C8CY00515J _journal_year 2018 _chemical_formula_moiety 'C32 H40 Cu N4, C F3 O3 S, 0.5(C H2 Cl2)' _chemical_formula_sum 'C33.5 H41 Cl Cu F3 N4 O3 S' _chemical_formula_weight 735.75 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 90 _cell_angle_beta 102.996(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.3905(3) _cell_length_b 19.0233(5) _cell_length_c 14.4810(3) _cell_measurement_reflns_used 4254 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 73.5040 _cell_measurement_theta_min 3.8830 _cell_volume 3325.86(14) _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 173(2) _diffrn_detector_area_resol_mean 10.4115 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.949 _diffrn_measurement_device_type 'Agilent Xcalibur PX Ultra A' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_unetI/netI 0.0484 _diffrn_reflns_Laue_measured_fraction_full 0.983 _diffrn_reflns_Laue_measured_fraction_max 0.949 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 10945 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.949 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.783 _diffrn_reflns_theta_min 3.901 _diffrn_source 'Enhance Ultra (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.744 _exptl_absorpt_correction_T_max 0.957 _exptl_absorpt_correction_T_min 0.604 _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 _exptl_crystal_density_diffrn 1.469 _exptl_crystal_description 'platy needles' _exptl_crystal_F_000 1532 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.438 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.060 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 479 _refine_ls_number_reflns 6376 _refine_ls_number_restraints 134 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0397 _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^)+(0.0516P)^2^+0.1585P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0984 _refine_ls_wR_factor_ref 0.1092 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4921 _reflns_number_total 6376 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8cy00515j2.cif _cod_data_source_block 7 _cod_original_cell_volume 3325.85(14) _cod_original_formula_sum 'C33.50 H41 Cl Cu F3 N4 O3 S' _cod_database_code 1550034 _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 ; SDG1603.res created by SHELXL-2014/7 TITL SDG1603 in P2(1)/n REM P2(1)/n (#14 in standard setting) REM BZ-511 CELL 1.54184 12.390501 19.023271 14.480985 90.0000 102.9961 90.0000 ZERR 4.00 0.000260 0.000549 0.000316 0.0000 0.0021 0.0000 LATT 1 SYMM -x+1/2, y+1/2,-z+1/2 SFAC C H Cu F N O S Cl UNIT 134 164 4 12 16 12 4 4 TEMP -100 L.S. 6 FMAP 2 PLAN 10 ACTA REM 'C32 H40 Cu N4, C F3 O3 S, 0.5(C H2 Cl2)' REM C33.5 H41 Cu F3 N4 O3 S Cl SADI S40 C40 S40' C40' SADI S40 O41 S40 O42 S40 O43 = S40' O41' S40' O42' S40' O43' SADI C40 F41 C40 F42 C40 F43 = C40' F41' C40' F42' C40' F43' SADI S40 F41 S40 F42 S40 F43 = S40' F41' S40' F42' S40' F43' SADI C40 O41 C40 O42 C40 O43 = C40' O41' C40' O42' C40' O43' SIMU 0.02 0.02 1 S40 S40' SIMU 0.02 0.02 4 O41 O41' SIMU 0.01 0.01 1 O42 O42' SIMU 0.02 0.02 1 O43 O43' SIMU 0.02 0.02 1 C40 C40' SIMU 0.02 0.02 4 F41 F41' SIMU 0.01 0.01 1 F42 F42' SIMU 0.02 0.02 1 F43 F43' SADI C50 CL1 C50 CL2 = C50' CL1' C50' CL2' SADI CL1 CL2 CL1' CL2' SIMU 0.02 0.02 1 C50 > CL2' WGHT 0.051600 0.158500 FVAR 3.12851 0.91246 0.84202 CU1 3 0.446826 0.254096 0.665149 11.00000 0.02711 0.03362 = 0.01381 -0.00041 0.00491 0.00034 N1 5 0.335114 0.197266 0.564101 11.00000 0.02564 0.02632 = 0.02035 -0.00099 0.00614 -0.00115 C2 1 0.249392 0.155951 0.571569 11.00000 0.03021 0.02869 = 0.02812 0.00050 0.01102 -0.00286 AFIX 43 H2A 2 0.234791 0.148726 0.632521 11.00000 -1.20000 AFIX 0 C3 1 0.181287 0.123387 0.494085 11.00000 0.03055 0.03346 = 0.03901 -0.00342 0.01065 -0.00814 AFIX 43 H3A 2 0.120784 0.095088 0.501865 11.00000 -1.20000 AFIX 0 C4 1 0.203283 0.132967 0.404966 11.00000 0.03141 0.03899 = 0.03043 -0.01053 0.00472 -0.00685 AFIX 43 H4A 2 0.158700 0.110724 0.350907 11.00000 -1.20000 AFIX 0 C5 1 0.291281 0.175480 0.396166 11.00000 0.02989 0.03849 = 0.02216 -0.00540 0.00626 -0.00395 AFIX 43 H5A 2 0.307803 0.183005 0.335971 11.00000 -1.20000 AFIX 0 C6 1 0.354994 0.206939 0.476993 11.00000 0.02555 0.02655 = 0.01901 -0.00210 0.00517 0.00050 C7 1 0.447006 0.254482 0.472646 11.00000 0.02468 0.03129 = 0.01686 -0.00033 0.00659 0.00060 AFIX 43 H7A 2 0.467245 0.262999 0.414139 11.00000 -1.20000 AFIX 0 N8 5 0.499408 0.284197 0.548444 11.00000 0.02129 0.02598 = 0.01757 0.00205 0.00472 0.00149 C9 1 0.593105 0.332168 0.545890 11.00000 0.02024 0.02526 = 0.01816 0.00047 0.00409 -0.00103 C10 1 0.624990 0.336517 0.450050 11.00000 0.02874 0.03410 = 0.02412 -0.00081 0.00703 -0.00210 AFIX 23 H10A 2 0.560892 0.353350 0.401261 11.00000 -1.20000 H10B 2 0.645462 0.289205 0.431193 11.00000 -1.20000 AFIX 0 C11 1 0.560916 0.405349 0.574634 11.00000 0.02629 0.03198 = 0.03159 -0.00187 0.00895 0.00125 AFIX 23 H11A 2 0.541372 0.402759 0.637181 11.00000 -1.20000 H11B 2 0.495232 0.422403 0.527745 11.00000 -1.20000 AFIX 0 C12 1 0.694027 0.306504 0.621079 11.00000 0.02572 0.03630 = 0.02605 0.00805 0.00268 0.00099 AFIX 23 H12A 2 0.716153 0.259143 0.603827 11.00000 -1.20000 H12B 2 0.674234 0.303195 0.683472 11.00000 -1.20000 AFIX 0 C13 1 0.723353 0.387165 0.456124 11.00000 0.03023 0.03678 = 0.02540 0.00295 0.01042 -0.00253 AFIX 13 H13A 2 0.743757 0.389522 0.393194 11.00000 -1.20000 AFIX 0 C14 1 0.657830 0.457036 0.579798 11.00000 0.03587 0.02518 = 0.03709 -0.00349 0.01039 -0.00178 AFIX 13 H14A 2 0.635967 0.504913 0.597518 11.00000 -1.20000 AFIX 0 C15 1 0.791761 0.358239 0.627512 11.00000 0.02401 0.04238 = 0.02956 0.00819 -0.00005 -0.00140 AFIX 13 H15A 2 0.856842 0.341504 0.676660 11.00000 -1.20000 AFIX 0 C16 1 0.688827 0.459832 0.482960 11.00000 0.03666 0.03663 = 0.03564 0.00996 0.00824 -0.00133 AFIX 23 H16A 2 0.624579 0.476521 0.434210 11.00000 -1.20000 H16B 2 0.750552 0.493369 0.485643 11.00000 -1.20000 AFIX 0 C17 1 0.757337 0.430620 0.654234 11.00000 0.03823 0.04728 = 0.02615 -0.00440 0.00720 -0.01419 AFIX 23 H17A 2 0.819950 0.463772 0.659064 11.00000 -1.20000 H17B 2 0.737840 0.428405 0.716824 11.00000 -1.20000 AFIX 0 C18 1 0.822376 0.361043 0.531069 11.00000 0.02672 0.04206 = 0.03968 0.00305 0.01247 0.00191 AFIX 23 H18A 2 0.886084 0.393075 0.534274 11.00000 -1.20000 H18B 2 0.844177 0.313626 0.513739 11.00000 -1.20000 AFIX 0 N21 5 0.560908 0.201328 0.769503 11.00000 0.02881 0.02833 = 0.01848 0.00142 0.00627 0.00388 C22 1 0.648182 0.161383 0.764853 11.00000 0.03988 0.03177 = 0.02934 0.00487 0.01362 0.00843 AFIX 43 H22A 2 0.661600 0.150972 0.704256 11.00000 -1.20000 AFIX 0 C23 1 0.720179 0.134382 0.844496 11.00000 0.03583 0.03535 = 0.04021 0.01149 0.01203 0.01262 AFIX 43 H23A 2 0.782035 0.106711 0.838431 11.00000 -1.20000 AFIX 0 C24 1 0.700244 0.148473 0.932581 11.00000 0.03194 0.03872 = 0.03237 0.01445 0.00392 0.00622 AFIX 43 H24A 2 0.747514 0.129890 0.988095 11.00000 -1.20000 AFIX 0 C25 1 0.610161 0.190191 0.939200 11.00000 0.03067 0.03908 = 0.02086 0.00695 0.00456 0.00074 AFIX 43 H25A 2 0.594518 0.200464 0.999052 11.00000 -1.20000 AFIX 0 C26 1 0.543478 0.216532 0.856071 11.00000 0.02440 0.02898 = 0.02001 0.00341 0.00512 -0.00274 C27 1 0.452958 0.265139 0.858148 11.00000 0.02531 0.03423 = 0.01468 0.00008 0.00530 0.00004 AFIX 43 H27A 2 0.433562 0.276250 0.916297 11.00000 -1.20000 AFIX 0 N28 5 0.399957 0.292643 0.780130 11.00000 0.02054 0.02636 = 0.01688 -0.00161 0.00403 -0.00253 C29 1 0.307796 0.342394 0.780536 11.00000 0.02078 0.02709 = 0.01738 -0.00189 0.00573 -0.00046 C30 1 0.282290 0.355010 0.877707 11.00000 0.03240 0.05349 = 0.01868 -0.00012 0.00887 0.01141 AFIX 23 H30A 2 0.348372 0.374700 0.921558 11.00000 -1.20000 H30B 2 0.263416 0.309886 0.904280 11.00000 -1.20000 AFIX 0 C31 1 0.336119 0.412628 0.739600 11.00000 0.03158 0.02875 = 0.04213 0.00350 0.01705 -0.00066 AFIX 23 H31A 2 0.352316 0.404740 0.676504 11.00000 -1.20000 H31B 2 0.402964 0.433015 0.781629 11.00000 -1.20000 AFIX 0 C32 1 0.204547 0.311682 0.713380 11.00000 0.02382 0.03251 = 0.02991 -0.00627 0.00127 -0.00204 AFIX 23 H32A 2 0.185194 0.266082 0.738381 11.00000 -1.20000 H32B 2 0.220209 0.303376 0.650180 11.00000 -1.20000 AFIX 0 C33 1 0.184664 0.406476 0.868097 11.00000 0.03821 0.05775 = 0.02541 -0.00297 0.01320 0.01396 AFIX 13 H33A 2 0.168691 0.414635 0.931931 11.00000 -1.20000 AFIX 0 C34 1 0.238586 0.464066 0.730517 11.00000 0.04288 0.03006 = 0.05367 0.00526 0.02242 0.00365 AFIX 13 H34A 2 0.257923 0.509821 0.704306 11.00000 -1.20000 AFIX 0 C35 1 0.106750 0.363131 0.704368 11.00000 0.02323 0.04339 = 0.03339 -0.00511 0.00033 0.00465 AFIX 13 H35A 2 0.039891 0.342813 0.660695 11.00000 -1.20000 AFIX 0 C36 1 0.214856 0.475978 0.828483 11.00000 0.03965 0.04231 = 0.05269 -0.01902 0.00901 0.00647 AFIX 23 H36A 2 0.281089 0.496126 0.871626 11.00000 -1.20000 H36B 2 0.152984 0.509705 0.823645 11.00000 -1.20000 AFIX 0 C37 1 0.135828 0.433210 0.664773 11.00000 0.04067 0.05024 = 0.03037 0.00909 0.01078 0.01862 AFIX 23 H37A 2 0.150025 0.426046 0.600832 11.00000 -1.20000 H37B 2 0.072964 0.466259 0.659154 11.00000 -1.20000 AFIX 0 C38 1 0.081885 0.375280 0.801771 11.00000 0.02890 0.04821 = 0.04279 0.00606 0.01728 0.00564 AFIX 23 H38A 2 0.061957 0.330212 0.827812 11.00000 -1.20000 H38B 2 0.018551 0.407954 0.796167 11.00000 -1.20000 AFIX 0 PART 1 S40 7 0.518394 0.661525 0.822080 21.00000 0.03093 0.03785 = 0.01943 -0.00177 0.00586 0.00112 O41 6 0.408403 0.637819 0.778412 21.00000 0.02811 0.06873 = 0.03032 -0.00431 0.00551 0.00117 O42 6 0.579328 0.694308 0.758687 21.00000 0.04464 0.05250 = 0.03035 0.00699 0.01069 -0.00622 O43 6 0.530336 0.694737 0.914045 21.00000 0.06141 0.04396 = 0.02318 -0.00679 0.00623 0.00495 C40 1 0.592513 0.579052 0.851700 21.00000 0.04182 0.04707 = 0.03613 -0.00018 0.01481 0.00563 F41 4 0.699395 0.589605 0.891735 21.00000 0.03675 0.10558 = 0.06299 0.01662 0.00494 0.02113 F42 4 0.551260 0.540748 0.913051 21.00000 0.07633 0.04720 = 0.05448 0.01715 0.02575 0.00726 F43 4 0.588669 0.538563 0.775557 21.00000 0.08797 0.05624 = 0.05358 -0.01289 0.02626 0.02120 PART 2 S40' 7 0.584312 0.666517 0.848213 -21.00000 0.02860 O41' 6 0.697027 0.646186 0.892972 -21.00000 0.03649 O42' 6 0.559316 0.704215 0.758479 -21.00000 0.02378 O43' 6 0.512722 0.700837 0.900494 -21.00000 0.02168 C40' 1 0.517298 0.582839 0.816365 -21.00000 0.03729 F41' 4 0.409031 0.589707 0.778780 -21.00000 0.06127 F42' 4 0.521406 0.540050 0.889944 -21.00000 0.05414 F43' 4 0.555515 0.548635 0.749424 -21.00000 0.04125 PART -1 C50 1 0.450707 0.020948 0.479911 30.50000 0.06802 0.05320 = 0.06915 0.01363 0.04638 0.00578 AFIX 23 H50A 2 0.453520 0.058084 0.432615 30.50000 -1.20000 H50B 2 0.373934 0.018246 0.488895 30.50000 -1.20000 AFIX 0 CL1 8 0.540209 0.041785 0.586300 30.50000 0.10526 0.12178 = 0.09193 -0.03785 0.05175 -0.07373 CL2 8 0.488748 -0.060525 0.438387 30.50000 0.05934 0.05042 = 0.07633 -0.01026 0.03134 0.00478 PART -2 C50' 1 0.477485 0.054836 0.531516 -30.50000 0.06959 AFIX 23 H50C 2 0.418146 0.064420 0.565572 -30.50000 -1.20000 H50D 2 0.504818 0.100505 0.513212 -30.50000 -1.20000 AFIX 0 CL1' 8 0.585686 0.010358 0.606638 -30.50000 0.07457 CL2' 8 0.423631 0.006189 0.430278 -30.50000 0.08596 PART 0 HKLF 4 REM SDG1603 in P2(1)/n REM R1 = 0.0397 for 4921 Fo > 4sig(Fo) and 0.0549 for all 6376 data REM 479 parameters refined using 134 restraints END WGHT 0.0515 0.1640 REM Highest difference peak 0.438, deepest hole -0.280, 1-sigma level 0.060 Q1 1 0.6553 0.2534 1.0144 11.00000 0.05 0.44 Q2 1 0.5811 0.1971 0.8969 11.00000 0.05 0.38 Q3 1 0.6137 0.3361 0.5032 11.00000 0.05 0.35 Q4 1 0.6400 0.3227 0.5761 11.00000 0.05 0.30 Q5 1 0.6041 0.1996 0.7646 11.00000 0.05 0.28 Q6 1 0.5554 0.3867 0.4723 11.00000 0.05 0.28 Q7 1 0.5125 0.2857 0.6186 11.00000 0.05 0.27 Q8 1 0.6829 0.4645 0.5394 11.00000 0.05 0.27 Q9 1 0.5463 0.2116 0.7306 11.00000 0.05 0.27 Q10 1 0.3221 0.1951 0.4396 11.00000 0.05 0.26 ; _shelx_res_checksum 31145 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 0.44683(2) 0.25410(2) 0.66515(2) 0.02480(10) Uani 1 1 d . . . . . N1 N 0.33511(14) 0.19727(10) 0.56410(12) 0.0240(4) Uani 1 1 d . . . . . C2 C 0.24939(19) 0.15595(12) 0.57157(16) 0.0283(4) Uani 1 1 d . . . . . H2A H 0.2348 0.1487 0.6325 0.034 Uiso 1 1 calc R U . . . C3 C 0.1813(2) 0.12339(14) 0.49408(18) 0.0339(5) Uani 1 1 d . . . . . H3A H 0.1208 0.0951 0.5019 0.041 Uiso 1 1 calc R U . . . C4 C 0.20328(19) 0.13297(14) 0.40497(17) 0.0340(5) Uani 1 1 d . . . . . H4A H 0.1587 0.1107 0.3509 0.041 Uiso 1 1 calc R U . . . C5 C 0.29128(19) 0.17548(13) 0.39617(15) 0.0301(5) Uani 1 1 d . . . . . H5A H 0.3078 0.1830 0.3360 0.036 Uiso 1 1 calc R U . . . C6 C 0.35499(17) 0.20694(12) 0.47699(14) 0.0237(4) Uani 1 1 d . . . . . C7 C 0.44701(17) 0.25448(12) 0.47265(14) 0.0240(4) Uani 1 1 d . . . . . H7A H 0.4672 0.2630 0.4141 0.029 Uiso 1 1 calc R U . . . N8 N 0.49941(14) 0.28420(10) 0.54844(12) 0.0216(3) Uani 1 1 d . . . . . C9 C 0.59311(16) 0.33217(11) 0.54589(14) 0.0213(4) Uani 1 1 d . . . . . C10 C 0.62499(18) 0.33652(13) 0.45005(15) 0.0288(4) Uani 1 1 d . . . . . H10A H 0.5609 0.3533 0.4013 0.035 Uiso 1 1 calc R U . . . H10B H 0.6455 0.2892 0.4312 0.035 Uiso 1 1 calc R U . . . C11 C 0.56092(18) 0.40535(13) 0.57463(16) 0.0296(5) Uani 1 1 d . . . . . H11A H 0.5414 0.4028 0.6372 0.035 Uiso 1 1 calc R U . . . H11B H 0.4952 0.4224 0.5277 0.035 Uiso 1 1 calc R U . . . C12 C 0.69403(18) 0.30650(13) 0.62108(15) 0.0299(5) Uani 1 1 d . . . . . H12A H 0.7162 0.2591 0.6038 0.036 Uiso 1 1 calc R U . . . H12B H 0.6742 0.3032 0.6835 0.036 Uiso 1 1 calc R U . . . C13 C 0.72335(19) 0.38716(13) 0.45612(15) 0.0301(5) Uani 1 1 d . . . . . H13A H 0.7438 0.3895 0.3932 0.036 Uiso 1 1 calc R U . . . C14 C 0.6578(2) 0.45704(13) 0.57980(17) 0.0324(5) Uani 1 1 d . . . . . H14A H 0.6360 0.5049 0.5975 0.039 Uiso 1 1 calc R U . . . C15 C 0.79176(18) 0.35824(14) 0.62751(17) 0.0329(5) Uani 1 1 d . . . . . H15A H 0.8568 0.3415 0.6767 0.040 Uiso 1 1 calc R U . . . C16 C 0.6888(2) 0.45983(14) 0.48296(18) 0.0363(5) Uani 1 1 d . . . . . H16A H 0.6246 0.4765 0.4342 0.044 Uiso 1 1 calc R U . . . H16B H 0.7506 0.4934 0.4856 0.044 Uiso 1 1 calc R U . . . C17 C 0.7573(2) 0.43062(15) 0.65423(17) 0.0372(6) Uani 1 1 d . . . . . H17A H 0.8199 0.4638 0.6591 0.045 Uiso 1 1 calc R U . . . H17B H 0.7378 0.4284 0.7168 0.045 Uiso 1 1 calc R U . . . C18 C 0.82238(19) 0.36104(15) 0.53107(18) 0.0354(5) Uani 1 1 d . . . . . H18A H 0.8861 0.3931 0.5343 0.042 Uiso 1 1 calc R U . . . H18B H 0.8442 0.3136 0.5137 0.042 Uiso 1 1 calc R U . . . N21 N 0.56091(15) 0.20133(10) 0.76950(12) 0.0251(4) Uani 1 1 d . . . . . C22 C 0.6482(2) 0.16138(13) 0.76485(17) 0.0327(5) Uani 1 1 d . . . . . H22A H 0.6616 0.1510 0.7043 0.039 Uiso 1 1 calc R U . . . C23 C 0.7202(2) 0.13438(14) 0.84450(18) 0.0366(5) Uani 1 1 d . . . . . H23A H 0.7820 0.1067 0.8384 0.044 Uiso 1 1 calc R U . . . C24 C 0.7002(2) 0.14847(14) 0.93258(17) 0.0349(5) Uani 1 1 d . . . . . H24A H 0.7475 0.1299 0.9881 0.042 Uiso 1 1 calc R U . . . C25 C 0.61016(19) 0.19019(14) 0.93920(15) 0.0304(5) Uani 1 1 d . . . . . H25A H 0.5945 0.2005 0.9991 0.036 Uiso 1 1 calc R U . . . C26 C 0.54348(17) 0.21653(12) 0.85607(15) 0.0244(4) Uani 1 1 d . . . . . C27 C 0.45296(17) 0.26514(12) 0.85815(14) 0.0246(4) Uani 1 1 d . . . . . H27A H 0.4336 0.2763 0.9163 0.030 Uiso 1 1 calc R U . . . N28 N 0.39996(13) 0.29264(10) 0.78013(11) 0.0213(3) Uani 1 1 d . . . . . C29 C 0.30780(16) 0.34239(11) 0.78054(13) 0.0215(4) Uani 1 1 d . . . . . C30 C 0.28229(19) 0.35501(15) 0.87771(15) 0.0344(5) Uani 1 1 d . . . . . H30A H 0.3484 0.3747 0.9216 0.041 Uiso 1 1 calc R U . . . H30B H 0.2634 0.3099 0.9043 0.041 Uiso 1 1 calc R U . . . C31 C 0.3361(2) 0.41263(13) 0.73960(18) 0.0328(5) Uani 1 1 d . . . . . H31A H 0.3523 0.4047 0.6765 0.039 Uiso 1 1 calc R U . . . H31B H 0.4030 0.4330 0.7816 0.039 Uiso 1 1 calc R U . . . C32 C 0.20455(18) 0.31168(13) 0.71338(16) 0.0295(5) Uani 1 1 d . . . . . H32A H 0.1852 0.2661 0.7384 0.035 Uiso 1 1 calc R U . . . H32B H 0.2202 0.3034 0.6502 0.035 Uiso 1 1 calc R U . . . C33 C 0.1847(2) 0.40648(17) 0.86810(17) 0.0395(6) Uani 1 1 d . . . . . H33A H 0.1687 0.4146 0.9319 0.047 Uiso 1 1 calc R U . . . C34 C 0.2386(2) 0.46407(14) 0.7305(2) 0.0404(6) Uani 1 1 d . . . . . H34A H 0.2579 0.5098 0.7043 0.048 Uiso 1 1 calc R U . . . C35 C 0.10675(18) 0.36313(15) 0.70437(17) 0.0343(5) Uani 1 1 d . . . . . H35A H 0.0399 0.3428 0.6607 0.041 Uiso 1 1 calc R U . . . C36 C 0.2149(2) 0.47598(16) 0.8285(2) 0.0451(6) Uani 1 1 d . . . . . H36A H 0.2811 0.4961 0.8716 0.054 Uiso 1 1 calc R U . . . H36B H 0.1530 0.5097 0.8236 0.054 Uiso 1 1 calc R U . . . C37 C 0.1358(2) 0.43321(16) 0.66477(17) 0.0400(6) Uani 1 1 d . . . . . H37A H 0.1500 0.4260 0.6008 0.048 Uiso 1 1 calc R U . . . H37B H 0.0730 0.4663 0.6592 0.048 Uiso 1 1 calc R U . . . C38 C 0.0819(2) 0.37528(16) 0.80177(19) 0.0385(6) Uani 1 1 d . . . . . H38A H 0.0620 0.3302 0.8278 0.046 Uiso 1 1 calc R U . . . H38B H 0.0186 0.4080 0.7962 0.046 Uiso 1 1 calc R U . . . S40 S 0.51839(5) 0.66153(4) 0.82208(4) 0.02938(19) Uani 0.912(2) 1 d D U P A 1 O41 O 0.40840(15) 0.63782(14) 0.77841(14) 0.0426(5) Uani 0.912(2) 1 d D U P A 1 O42 O 0.5793(3) 0.69431(18) 0.7587(2) 0.0421(9) Uani 0.912(2) 1 d D U P A 1 O43 O 0.5303(3) 0.69474(18) 0.9140(2) 0.0434(10) Uani 0.912(2) 1 d D U P A 1 C40 C 0.5925(2) 0.57905(17) 0.8517(2) 0.0407(6) Uani 0.912(2) 1 d D U P A 1 F41 F 0.69940(16) 0.58960(16) 0.89173(16) 0.0694(7) Uani 0.912(2) 1 d D U P A 1 F42 F 0.5513(3) 0.54075(13) 0.91305(19) 0.0576(7) Uani 0.912(2) 1 d D U P A 1 F43 F 0.5887(3) 0.53856(13) 0.77556(19) 0.0643(7) Uani 0.912(2) 1 d D U P A 1 S40' S 0.5843(6) 0.6665(3) 0.8482(5) 0.0286(19) Uiso 0.088(2) 1 d D U P A 2 O41' O 0.6970(11) 0.6462(11) 0.8930(14) 0.036(4) Uiso 0.088(2) 1 d D U P A 2 O42' O 0.559(3) 0.7042(14) 0.7585(18) 0.024(5) Uiso 0.088(2) 1 d D U P A 2 O43' O 0.513(3) 0.7008(14) 0.900(3) 0.022(6) Uiso 0.088(2) 1 d D U P A 2 C40' C 0.5173(13) 0.5828(8) 0.8164(12) 0.037(5) Uiso 0.088(2) 1 d D U P A 2 F41' F 0.4090(13) 0.5897(13) 0.7788(16) 0.061(5) Uiso 0.088(2) 1 d D U P A 2 F42' F 0.521(3) 0.5401(12) 0.890(2) 0.054(5) Uiso 0.088(2) 1 d D U P A 2 F43' F 0.5555(19) 0.5486(10) 0.7494(15) 0.041(6) Uiso 0.088(2) 1 d D U P A 2 C50 C 0.4507(8) 0.0209(4) 0.4799(7) 0.059(2) Uani 0.421(5) 1 d D U P B -1 H50A H 0.4535 0.0581 0.4326 0.070 Uiso 0.421(5) 1 calc R U P B -1 H50B H 0.3739 0.0182 0.4889 0.070 Uiso 0.421(5) 1 calc R U P B -1 Cl1 Cl 0.5402(8) 0.0418(6) 0.5863(5) 0.102(4) Uani 0.421(5) 1 d D U P B -1 Cl2 Cl 0.4887(4) -0.0605(3) 0.4384(4) 0.0595(11) Uani 0.421(5) 1 d D . P B -1 C50' C 0.477(5) 0.055(3) 0.532(3) 0.070(11) Uiso 0.079(5) 1 d D U P B -2 H50C H 0.4181 0.0644 0.5656 0.084 Uiso 0.079(5) 1 calc R U P B -2 H50D H 0.5048 0.1005 0.5132 0.084 Uiso 0.079(5) 1 calc R U P B -2 Cl1' Cl 0.5857(17) 0.0104(13) 0.6066(13) 0.075(5) Uiso 0.079(5) 1 d D U P B -2 Cl2' Cl 0.4236(15) 0.0062(13) 0.4303(14) 0.086(5) Uiso 0.079(5) 1 d D U P B -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 0.02711(17) 0.03362(18) 0.01381(15) -0.00041(12) 0.00491(11) 0.00034(13) N1 0.0256(8) 0.0263(9) 0.0204(8) -0.0010(7) 0.0061(6) -0.0011(7) C2 0.0302(10) 0.0287(11) 0.0281(11) 0.0005(9) 0.0110(8) -0.0029(9) C3 0.0306(11) 0.0335(12) 0.0390(12) -0.0034(10) 0.0107(9) -0.0081(10) C4 0.0314(11) 0.0390(13) 0.0304(11) -0.0105(10) 0.0047(9) -0.0068(10) C5 0.0299(11) 0.0385(12) 0.0222(10) -0.0054(9) 0.0063(8) -0.0039(9) C6 0.0256(9) 0.0265(10) 0.0190(9) -0.0021(8) 0.0052(7) 0.0005(8) C7 0.0247(9) 0.0313(11) 0.0169(9) -0.0003(8) 0.0066(7) 0.0006(8) N8 0.0213(8) 0.0260(9) 0.0176(7) 0.0020(7) 0.0047(6) 0.0015(7) C9 0.0202(9) 0.0253(10) 0.0182(9) 0.0005(7) 0.0041(7) -0.0010(8) C10 0.0287(10) 0.0341(12) 0.0241(10) -0.0008(9) 0.0070(8) -0.0021(9) C11 0.0263(10) 0.0320(11) 0.0316(11) -0.0019(9) 0.0089(8) 0.0013(9) C12 0.0257(10) 0.0363(12) 0.0260(10) 0.0081(9) 0.0027(8) 0.0010(9) C13 0.0302(11) 0.0368(12) 0.0254(10) 0.0029(9) 0.0104(8) -0.0025(9) C14 0.0359(12) 0.0252(11) 0.0371(12) -0.0035(9) 0.0104(9) -0.0018(9) C15 0.0240(10) 0.0424(13) 0.0296(11) 0.0082(10) 0.0000(8) -0.0014(9) C16 0.0367(12) 0.0366(13) 0.0356(12) 0.0100(10) 0.0082(10) -0.0013(10) C17 0.0382(12) 0.0473(15) 0.0262(11) -0.0044(10) 0.0072(9) -0.0142(11) C18 0.0267(11) 0.0421(13) 0.0397(13) 0.0031(11) 0.0125(9) 0.0019(10) N21 0.0288(9) 0.0283(9) 0.0185(8) 0.0014(7) 0.0063(6) 0.0039(7) C22 0.0399(12) 0.0318(12) 0.0293(11) 0.0049(9) 0.0136(9) 0.0084(10) C23 0.0358(12) 0.0353(12) 0.0402(13) 0.0115(11) 0.0120(10) 0.0126(10) C24 0.0319(11) 0.0387(13) 0.0324(12) 0.0145(10) 0.0039(9) 0.0062(10) C25 0.0307(11) 0.0391(13) 0.0209(10) 0.0070(9) 0.0046(8) 0.0007(10) C26 0.0244(9) 0.0290(11) 0.0200(9) 0.0034(8) 0.0051(7) -0.0027(8) C27 0.0253(9) 0.0342(11) 0.0147(9) 0.0001(8) 0.0053(7) 0.0000(8) N28 0.0205(8) 0.0264(9) 0.0169(7) -0.0016(6) 0.0040(6) -0.0025(7) C29 0.0208(9) 0.0271(10) 0.0174(9) -0.0019(8) 0.0057(7) -0.0005(8) C30 0.0324(11) 0.0535(15) 0.0187(10) -0.0001(10) 0.0089(8) 0.0114(11) C31 0.0316(11) 0.0287(11) 0.0421(12) 0.0035(10) 0.0171(9) -0.0007(9) C32 0.0238(10) 0.0325(12) 0.0299(11) -0.0063(9) 0.0013(8) -0.0020(9) C33 0.0382(12) 0.0578(17) 0.0254(11) -0.0030(11) 0.0132(9) 0.0140(12) C34 0.0429(13) 0.0301(12) 0.0537(15) 0.0053(11) 0.0224(11) 0.0037(11) C35 0.0232(10) 0.0434(14) 0.0334(12) -0.0051(10) 0.0003(8) 0.0047(10) C36 0.0397(13) 0.0423(15) 0.0527(16) -0.0190(13) 0.0090(11) 0.0065(12) C37 0.0407(13) 0.0502(16) 0.0304(11) 0.0091(11) 0.0108(10) 0.0186(12) C38 0.0289(11) 0.0482(15) 0.0428(13) 0.0061(12) 0.0173(10) 0.0056(10) S40 0.0309(4) 0.0379(3) 0.0194(3) -0.0018(2) 0.0059(2) 0.0011(2) O41 0.0281(9) 0.0687(16) 0.0303(9) -0.0043(10) 0.0055(7) 0.0012(9) O42 0.045(2) 0.0525(17) 0.0303(10) 0.0070(10) 0.0107(10) -0.0062(15) O43 0.061(2) 0.0440(15) 0.0232(14) -0.0068(12) 0.0062(14) 0.0050(13) C40 0.0418(15) 0.0471(17) 0.0361(14) -0.0002(13) 0.0148(11) 0.0056(13) F41 0.0368(10) 0.106(2) 0.0630(12) 0.0166(13) 0.0049(8) 0.0211(11) F42 0.076(2) 0.0472(12) 0.0545(15) 0.0172(10) 0.0257(13) 0.0073(11) F43 0.0880(19) 0.0562(14) 0.0536(13) -0.0129(11) 0.0263(13) 0.0212(13) C50 0.068(5) 0.053(5) 0.069(6) 0.014(4) 0.046(5) 0.006(4) Cl1 0.105(6) 0.122(7) 0.092(4) -0.038(5) 0.052(5) -0.074(6) Cl2 0.0593(17) 0.0504(13) 0.076(3) -0.0103(14) 0.0313(18) 0.0048(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 142.27(8) N28 Cu1 N1 119.99(7) N8 Cu1 N1 81.25(7) N28 Cu1 N21 81.42(7) N8 Cu1 N21 116.67(7) N1 Cu1 N21 119.79(8) C2 N1 C6 117.88(18) C2 N1 Cu1 131.35(15) C6 N1 Cu1 110.75(14) N1 C2 C3 122.9(2) C2 C3 C4 118.8(2) C5 C4 C3 119.0(2) C4 C5 C6 118.9(2) N1 C6 C5 122.6(2) N1 C6 C7 115.50(18) C5 C6 C7 121.89(19) N8 C7 C6 119.11(18) C7 N8 C9 120.07(17) C7 N8 Cu1 113.32(15) C9 N8 Cu1 126.51(13) N8 C9 C10 114.80(16) N8 C9 C11 107.42(16) C10 C9 C11 109.51(18) N8 C9 C12 107.62(17) C10 C9 C12 108.93(17) C11 C9 C12 108.39(18) C9 C10 C13 110.17(18) C9 C11 C14 110.22(18) C9 C12 C15 109.93(18) C16 C13 C18 109.9(2) C16 C13 C10 108.56(19) C18 C13 C10 109.6(2) C17 C14 C16 109.1(2) C17 C14 C11 108.7(2) C16 C14 C11 109.27(19) C17 C15 C18 110.1(2) C17 C15 C12 109.36(19) C18 C15 C12 108.6(2) C13 C16 C14 110.1(2) C15 C17 C14 110.30(19) C13 C18 C15 109.63(19) C22 N21 C26 117.97(19) C22 N21 Cu1 131.56(15) C26 N21 Cu1 110.28(14) N21 C22 C23 123.0(2) C24 C23 C22 118.8(2) C23 C24 C25 119.2(2) C24 C25 C26 118.4(2) N21 C26 C25 122.6(2) N21 C26 C27 116.04(18) C25 C26 C27 121.3(2) N28 C27 C26 118.92(18) C27 N28 C29 119.88(17) C27 N28 Cu1 113.10(15) C29 N28 Cu1 126.78(12) N28 C29 C30 114.97(17) N28 C29 C31 108.11(16) C30 C29 C31 109.36(19) N28 C29 C32 106.66(17) C30 C29 C32 109.08(18) C31 C29 C32 108.46(18) C29 C30 C33 109.74(18) C29 C31 C34 110.10(18) C29 C32 C35 109.81(19) C36 C33 C38 109.9(2) C36 C33 C30 109.4(2) C38 C33 C30 109.6(2) C37 C34 C36 109.2(2) C37 C34 C31 109.8(2) C36 C34 C31 109.1(2) C37 C35 C38 109.2(2) C37 C35 C32 109.8(2) C38 C35 C32 109.6(2) C33 C36 C34 109.6(2) C34 C37 C35 109.6(2) C35 C38 C33 109.01(19) O41 S40 O43 115.50(18) O41 S40 O42 115.58(17) O43 S40 O42 115.6(2) O41 S40 C40 102.19(15) O43 S40 C40 102.54(18) O42 S40 C40 102.27(18) F41 C40 F42 106.5(3) F41 C40 F43 107.0(3) F42 C40 F43 106.6(3) F41 C40 S40 111.8(2) F42 C40 S40 112.2(2) F43 C40 S40 112.3(2) O43' S40' O41' 121.9(19) O43' S40' O42' 102(2) O41' S40' O42' 121.3(19) O43' S40' C40' 103.3(11) O41' S40' C40' 102.7(9) O42' S40' C40' 102.3(11) F42' C40' F41' 104(2) F42' C40' F43' 109(2) F41' C40' F43' 103.8(18) F42' C40' S40' 113.7(13) F41' C40' S40' 112.3(12) F43' C40' S40' 113.3(12) Cl1 C50 Cl2 109.8(6) Cl2' C50' Cl1' 111.3(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cu1 N28 2.0204(17) Cu1 N8 2.0258(17) Cu1 N1 2.0772(18) Cu1 N21 2.0805(18) N1 C2 1.345(3) N1 C6 1.351(3) C2 C3 1.389(3) C3 C4 1.390(4) C4 C5 1.386(3) C5 C6 1.391(3) C6 C7 1.468(3) C7 N8 1.275(3) N8 C9 1.484(3) C9 C10 1.528(3) C9 C11 1.531(3) C9 C12 1.541(3) C10 C13 1.541(3) C11 C14 1.541(3) C12 C15 1.547(3) C13 C16 1.523(4) C13 C18 1.527(3) C14 C17 1.529(4) C14 C16 1.536(3) C15 C17 1.517(4) C15 C18 1.528(3) N21 C22 1.336(3) N21 C26 1.350(3) C22 C23 1.388(3) C23 C24 1.379(4) C24 C25 1.390(4) C25 C26 1.391(3) C26 C27 1.459(3) C27 N28 1.284(3) N28 C29 1.484(3) C29 C30 1.529(3) C29 C31 1.534(3) C29 C32 1.538(3) C30 C33 1.538(3) C31 C34 1.537(3) C32 C35 1.540(3) C33 C36 1.521(4) C33 C38 1.532(4) C34 C37 1.525(4) C34 C36 1.529(4) C35 C37 1.526(4) C35 C38 1.527(3) S40 O41 1.440(2) S40 O43 1.451(3) S40 O42 1.454(3) S40 C40 1.820(3) C40 F41 1.336(4) C40 F42 1.336(4) C40 F43 1.337(4) S40' O43' 1.445(15) S40' O41' 1.454(13) S40' O42' 1.455(15) S40' C40' 1.807(14) C40' F42' 1.333(15) C40' F41' 1.336(14) C40' F43' 1.339(14) C50 Cl1 1.730(11) C50 Cl2 1.764(9) C50' Cl2' 1.735(18) C50' Cl1' 1.744(18)