#------------------------------------------------------------------------------ #$Date: 2021-01-14 07:06:55 +0200 (Thu, 14 Jan 2021) $ #$Revision: 260948 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560090.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_1560090 loop_ _publ_author_name 'Payne, Jack' 'McKeown, Paul' 'Driscoll, Oliver' 'Kociok-K\"ohn, Gabriele' 'Emanuelsson, Emma Anna Carolina' 'Jones, Matthew' _publ_section_title ; Make or Break: Mg(II)- and Zn(II)-Catalen Complexes for PLA Production and Recycling of Commodity Polyesters ; _journal_name_full 'Polymer Chemistry' _journal_paper_doi 10.1039/D0PY01519A _journal_year 2021 _chemical_formula_sum 'C30 H36 Br2 N2 O2 Zn' _chemical_formula_weight 681.80 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2020-10-29 deposited with the CCDC. 2020-12-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.646(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.0556(3) _cell_length_b 14.2825(3) _cell_length_c 20.6880(4) _cell_measurement_reflns_used 10106 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 72.7070 _cell_measurement_theta_min 3.1060 _cell_volume 2956.78(12) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565' _computing_publication_material ; 'WinGX publication routines, Farrugia, L. J., J. Appl. Crystallogr., 1999, 32, 837-838 ; _computing_structure_refinement ; SHELXL-2014/8 (Sheldrick, 2014) Sheldrick GM (2008) Acta Crystallogr A64:112-122 and C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich ShelXle: a Qt graphical user interface for SHELXL J. Appl. Cryst., 44, (2011) 1281-1284. ; _computing_structure_solution ; SHELXT Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. ; _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.1150 _diffrn_detector_type EosS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, EosS2' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_unetI/netI 0.0215 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 15599 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 72.128 _diffrn_reflns_theta_min 3.767 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 4.541 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.91249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.532 _exptl_crystal_description cube _exptl_crystal_F_000 1384 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 2.145 _refine_diff_density_min -1.312 _refine_diff_density_rms 0.082 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 372 _refine_ls_number_reflns 5840 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0408 _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^)+(0.0438P)^2^+6.4600P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1003 _refine_ls_wR_factor_ref 0.1019 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5538 _reflns_number_total 5840 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0py01519a2.cif _cod_data_source_block Zn(3)2 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1560090 _shelx_shelxl_version_number 2017/1 _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. ; _oxdiff_exptl_absorpt_empirical_full_min 0.831 _oxdiff_exptl_absorpt_empirical_full_max 1.140 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; REM Old TITL s20mdj5 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.117, Rweak 0.023, Alpha 0.044, Orientation as input REM Formula found by SHELXT: C31 N4 O2 Zn Br2 REM shelxt_a.res in P2(1)/c REM R1 = 0.0531 for 4906 Fo > 4sig(Fo) and 0.0556 for all 5224 data REM 335 parameters refined using 0 restraints REM Highest difference peak 2.297, deepest hole -1.100, 1-sigma level 0.121 REM shelxt_a.res in P2(1)/c REM R1 = 0.0386 for 5538 Fo > 4sig(Fo) and 0.0404 for all 5840 data REM 376 parameters refined using 0 restraints REM Highest difference peak 2.059, deepest hole -1.315, 1-sigma level 0.078 REM shelxt_a.res in P2(1)/c REM R1 = 0.0422 for 5538 Fo > 4sig(Fo) and 0.0440 for all 5840 data REM 372 parameters refined using 0 restraints REM Highest difference peak 2.393, deepest hole -1.301, 1-sigma level 0.087 TITL shelxt_a.res in P2(1)/c C:\WORK\XSTALS\2020\s20mdj5\s20mdj5.res created by SHELXL-2017/1 at 17:09:49 on 24-Feb-2020 CELL 1.54184 10.0556 14.2825 20.6880 90.000 95.646 90.000 ZERR 4.0000 0.0003 0.0003 0.0004 0.000 0.002 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O ZN BR UNIT 120 144 8 8 4 8 MERG 2 SHEL 99999.00 0.81 FMAP GRID PLAN TEMP -123 BOND $H L.S. 20 ACTA WGHT 0.043800 6.460000 FVAR 2.92955 0.00000 BR1 6 -0.014722 0.245127 0.322198 11.00000 0.06112 0.02736 = 0.04373 -0.00515 0.00924 -0.01762 ZN1 5 0.041401 0.539358 0.442864 11.00000 0.02240 0.01815 = 0.02806 0.00258 -0.00850 -0.00586 O1 4 0.139438 0.484256 0.525518 11.00000 0.01987 0.01745 = 0.02844 0.00065 -0.00849 -0.00421 N1 3 0.073246 0.664824 0.505141 11.00000 0.02014 0.01833 = 0.03567 0.00283 -0.01088 -0.00194 AFIX 13 H1 2 -0.000243 0.671496 0.534056 11.00000 -1.20000 AFIX 0 C1 1 0.227007 0.549004 0.553466 11.00000 0.01783 0.01892 = 0.02474 -0.00033 -0.00389 -0.00453 BR2 6 0.219508 0.409568 0.112774 11.00000 0.05367 0.05154 = 0.03997 -0.00374 0.01181 -0.01002 O2 4 0.040451 0.433313 0.381745 11.00000 0.03421 0.02156 = 0.03144 -0.00123 0.00007 -0.00747 N2 3 0.120337 0.626267 0.379326 11.00000 0.02514 0.02087 = 0.03398 0.00456 -0.00881 -0.00643 C2 1 0.345438 0.522733 0.591050 11.00000 0.01829 0.02021 = 0.02223 0.00178 -0.00292 -0.00067 C3 1 0.429694 0.594616 0.616007 11.00000 0.01611 0.02640 = 0.02474 0.00051 -0.00485 -0.00188 AFIX 43 H3 2 0.509861 0.577650 0.641470 11.00000 -1.20000 AFIX 0 C4 1 0.403669 0.689495 0.605943 11.00000 0.01932 0.02333 = 0.02444 -0.00370 -0.00316 -0.00508 C5 1 0.285622 0.713191 0.568371 11.00000 0.02373 0.01757 = 0.02961 -0.00053 -0.00332 -0.00227 AFIX 43 H5 2 0.264432 0.777172 0.560105 11.00000 -1.20000 AFIX 0 C6 1 0.199375 0.644164 0.543121 11.00000 0.01656 0.02142 = 0.02794 0.00063 -0.00603 -0.00119 C7 1 0.380625 0.419407 0.604374 11.00000 0.02181 0.02267 = 0.03177 0.00363 -0.00620 0.00071 C8 1 0.275472 0.374503 0.643630 11.00000 0.03171 0.03037 = 0.04419 0.01339 -0.00331 -0.00306 AFIX 137 H8A 2 0.188465 0.374771 0.617727 11.00000 -1.50000 H8B 2 0.269360 0.410228 0.683672 11.00000 -1.50000 H8C 2 0.301481 0.309852 0.654543 11.00000 -1.50000 AFIX 0 C9 1 0.517111 0.408438 0.643692 11.00000 0.02684 0.03053 = 0.05913 0.01119 -0.01659 0.00196 AFIX 137 H9A 2 0.535891 0.341814 0.651361 11.00000 -1.50000 H9B 2 0.516143 0.440769 0.685425 11.00000 -1.50000 H9C 2 0.586549 0.435719 0.619423 11.00000 -1.50000 AFIX 0 C10 1 0.387778 0.366880 0.540479 11.00000 0.04698 0.02799 = 0.04368 -0.00470 -0.00191 0.01158 AFIX 137 H10A 2 0.300471 0.369355 0.514913 11.00000 -1.50000 H10B 2 0.412258 0.301457 0.549633 11.00000 -1.50000 H10C 2 0.455195 0.396134 0.515906 11.00000 -1.50000 AFIX 0 C11 1 0.499821 0.764929 0.635609 11.00000 0.02483 0.02796 = 0.03298 -0.00746 -0.00477 -0.00794 PART 1 C12 1 0.618649 0.728788 0.675508 10.50000 0.04151 0.03844 = 0.08460 -0.00681 -0.03815 -0.00706 AFIX 137 H12A 2 0.590163 0.689933 0.710677 10.50000 -1.50000 H12B 2 0.672155 0.781404 0.694025 10.50000 -1.50000 H12C 2 0.672473 0.691048 0.648294 10.50000 -1.50000 AFIX 0 C13 1 0.423186 0.832268 0.675660 10.50000 0.03967 0.06309 = 0.08021 -0.04556 -0.00438 -0.00435 AFIX 137 H13A 2 0.378052 0.796810 0.707680 10.50000 -1.50000 H13B 2 0.356647 0.866296 0.646861 10.50000 -1.50000 H13C 2 0.485666 0.876922 0.698147 10.50000 -1.50000 AFIX 0 C14 1 0.544902 0.825029 0.579976 10.50000 0.06189 0.04708 = 0.06020 -0.00016 -0.00722 -0.03547 AFIX 137 H14A 2 0.598752 0.877696 0.598154 10.50000 -1.50000 H14B 2 0.466189 0.848940 0.553366 10.50000 -1.50000 H14C 2 0.598462 0.786714 0.552989 10.50000 -1.50000 PART 0 AFIX 0 C15 1 0.072034 0.743850 0.459252 11.00000 0.03038 0.01602 = 0.04142 0.00376 -0.01385 -0.00120 AFIX 23 H15A 2 0.107869 0.800618 0.482264 11.00000 -1.20000 H15B 2 -0.020848 0.757001 0.441059 11.00000 -1.20000 AFIX 0 C16 1 0.156634 0.719891 0.404817 11.00000 0.03431 0.01796 = 0.03840 0.00667 -0.00909 -0.00935 AFIX 23 H16A 2 0.141795 0.766839 0.369640 11.00000 -1.20000 H16B 2 0.252436 0.721093 0.421312 11.00000 -1.20000 AFIX 0 C17 1 0.151398 0.602939 0.323022 11.00000 0.02146 0.02500 = 0.03677 0.01031 -0.00723 -0.00522 AFIX 43 H17 2 0.191667 0.649792 0.298814 11.00000 -1.20000 AFIX 0 C18 1 0.131111 0.511954 0.292577 11.00000 0.02011 0.02660 = 0.03361 0.00321 -0.00732 -0.00333 C19 1 0.173145 0.502931 0.230321 11.00000 0.02510 0.03385 = 0.03559 0.00656 -0.00326 -0.00549 AFIX 43 H19 2 0.211187 0.555431 0.210777 11.00000 -1.20000 AFIX 0 C20 1 0.160613 0.420292 0.197121 11.00000 0.02731 0.04066 = 0.03157 0.00279 0.00003 -0.00174 C21 1 0.103336 0.341826 0.223941 11.00000 0.02873 0.03081 = 0.03459 -0.00217 -0.00485 -0.00129 AFIX 43 H21 2 0.093257 0.284548 0.200629 11.00000 -1.20000 AFIX 0 C22 1 0.062216 0.350239 0.284945 11.00000 0.02696 0.02467 = 0.03370 0.00242 -0.00413 -0.00603 C23 1 0.076267 0.433249 0.323484 11.00000 0.01933 0.02455 = 0.03260 0.00171 -0.00662 -0.00248 C24 1 0.895259 0.953720 0.572143 11.00000 0.06681 0.08361 = 0.06402 0.01399 0.00714 -0.00750 AFIX 137 H24A 2 0.975366 0.945532 0.602632 11.00000 -1.50000 H24B 2 0.919200 0.985996 0.533122 11.00000 -1.50000 H24C 2 0.857106 0.892287 0.560091 11.00000 -1.50000 AFIX 0 C25 1 0.793673 1.011292 0.603878 11.00000 0.05512 0.04502 = 0.06722 0.01454 0.00022 -0.01802 C26 1 0.800540 1.022029 0.669276 11.00000 0.04535 0.04917 = 0.07474 0.01756 -0.00507 -0.01263 AFIX 43 H26 2 0.872245 0.994129 0.695829 11.00000 -1.20000 AFIX 0 C27 1 0.703812 1.073523 0.698420 11.00000 0.07439 0.05806 = 0.08775 0.00786 0.00991 -0.02507 AFIX 43 H27 2 0.709676 1.081470 0.744203 11.00000 -1.20000 AFIX 0 C28 1 0.597375 1.113270 0.657819 11.00000 0.05418 0.04501 = 0.10919 0.00838 0.00764 -0.00947 AFIX 43 H28 2 0.529526 1.148391 0.675639 11.00000 -1.20000 AFIX 0 C29 1 0.594445 1.099935 0.592260 11.00000 0.05530 0.04548 = 0.10140 0.01564 -0.00409 -0.01071 AFIX 43 H29 2 0.522507 1.125911 0.564814 11.00000 -1.20000 AFIX 0 C30 1 0.689871 1.051220 0.564827 11.00000 0.06104 0.04769 = 0.08761 0.01838 -0.01053 -0.01895 AFIX 43 H30 2 0.685325 1.044598 0.518971 11.00000 -1.20000 PART 2 AFIX 0 C12A 1 0.521396 0.747300 0.709922 10.50000 0.07387 0.05621 = 0.02768 -0.00960 -0.01269 -0.02792 AFIX 137 H12D 2 0.583044 0.794350 0.730182 10.50000 -1.50000 H12E 2 0.559227 0.684688 0.718109 10.50000 -1.50000 H12F 2 0.435543 0.751729 0.728402 10.50000 -1.50000 AFIX 0 C13A 1 0.452567 0.862791 0.624425 10.50000 0.03512 0.02759 = 0.06226 -0.01615 -0.00927 -0.01048 AFIX 137 H13D 2 0.448125 0.877220 0.577951 10.50000 -1.50000 H13E 2 0.514854 0.905942 0.648588 10.50000 -1.50000 H13F 2 0.363580 0.869704 0.639365 10.50000 -1.50000 AFIX 0 C14A 1 0.638242 0.753669 0.609605 10.50000 0.02320 0.04134 = 0.06407 -0.01711 0.00196 -0.01622 AFIX 137 H14D 2 0.628757 0.761037 0.562279 10.50000 -1.50000 H14E 2 0.674087 0.691345 0.620911 10.50000 -1.50000 H14F 2 0.699445 0.801503 0.629176 10.50000 -1.50000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)/c REM R1 = 0.0408 for 5538 Fo > 4sig(Fo) and 0.0426 for all 5840 data REM 372 parameters refined using 0 restraints END WGHT 0.0433 6.5021 REM Highest difference peak 2.145, deepest hole -1.312, 1-sigma level 0.082 Q1 1 -0.0427 0.6859 0.5471 11.00000 0.05 2.14 Q2 1 -0.0989 0.2701 0.3152 11.00000 0.05 2.06 Q3 1 0.1512 0.4367 0.1101 11.00000 0.05 1.10 Q4 1 0.7810 1.0386 0.7200 11.00000 0.05 0.41 Q5 1 0.7316 1.0029 0.5230 11.00000 0.05 0.39 Q6 1 0.2391 0.4043 0.1466 11.00000 0.05 0.37 Q7 1 0.7472 1.0596 0.7422 11.00000 0.05 0.36 Q8 1 0.2111 0.5989 0.5555 11.00000 0.05 0.36 Q9 1 0.6369 1.1161 0.7192 11.00000 0.05 0.35 Q10 1 0.3050 0.5334 0.5641 11.00000 0.05 0.35 Q11 1 0.2285 0.3728 0.0917 11.00000 0.05 0.33 Q12 1 0.0047 0.2433 0.3569 11.00000 0.05 0.32 Q13 1 0.3638 0.4738 0.5941 11.00000 0.05 0.29 Q14 1 0.3777 0.5622 0.6067 11.00000 0.05 0.29 Q15 1 0.1674 0.4965 0.2706 11.00000 0.05 0.28 Q16 1 0.4103 0.6384 0.6135 11.00000 0.05 0.27 Q17 1 0.1306 0.3776 0.2154 11.00000 0.05 0.27 Q18 1 0.1240 0.4760 0.3087 11.00000 0.05 0.25 Q19 1 0.3379 0.6983 0.5961 11.00000 0.05 0.24 Q20 1 0.3309 0.3984 0.6232 11.00000 0.05 0.24 ; _shelx_res_checksum 98466 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Br1 Br -0.01472(4) 0.24513(2) 0.32220(2) 0.04380(12) Uani 1 1 d . . . . . Zn1 Zn 0.04140(4) 0.53936(2) 0.44286(2) 0.02360(10) Uani 1 1 d . . . . . O1 O 0.13944(18) 0.48426(13) 0.52552(9) 0.0226(4) Uani 1 1 d . . . . . N1 N 0.0732(2) 0.66482(16) 0.50514(12) 0.0256(5) Uani 1 1 d . . . . . H1 H -0.000243 0.671496 0.534056 0.031 Uiso 1 1 calc R U . . . C1 C 0.2270(3) 0.54900(19) 0.55347(13) 0.0209(5) Uani 1 1 d . . . . . Br2 Br 0.21951(4) 0.40957(3) 0.11277(2) 0.04792(12) Uani 1 1 d . . . . . O2 O 0.0405(2) 0.43331(14) 0.38175(10) 0.0293(4) Uani 1 1 d . . . . . N2 N 0.1203(2) 0.62627(17) 0.37933(12) 0.0274(5) Uani 1 1 d . . . . . C2 C 0.3454(3) 0.52273(19) 0.59105(13) 0.0206(5) Uani 1 1 d . . . . . C3 C 0.4297(3) 0.5946(2) 0.61601(13) 0.0229(5) Uani 1 1 d . . . . . H3 H 0.509861 0.577650 0.641470 0.027 Uiso 1 1 calc R U . . . C4 C 0.4037(3) 0.6895(2) 0.60594(13) 0.0227(5) Uani 1 1 d . . . . . C5 C 0.2856(3) 0.71319(19) 0.56837(14) 0.0240(5) Uani 1 1 d . . . . . H5 H 0.264432 0.777172 0.560105 0.029 Uiso 1 1 calc R U . . . C6 C 0.1994(3) 0.64416(19) 0.54312(13) 0.0225(5) Uani 1 1 d . . . . . C7 C 0.3806(3) 0.4194(2) 0.60437(14) 0.0260(6) Uani 1 1 d . . . . . C8 C 0.2755(3) 0.3745(2) 0.64363(17) 0.0359(7) Uani 1 1 d . . . . . H8A H 0.188465 0.374771 0.617727 0.054 Uiso 1 1 calc R U . . . H8B H 0.269360 0.410228 0.683672 0.054 Uiso 1 1 calc R U . . . H8C H 0.301481 0.309852 0.654543 0.054 Uiso 1 1 calc R U . . . C9 C 0.5171(3) 0.4084(2) 0.64369(19) 0.0402(8) Uani 1 1 d . . . . . H9A H 0.535891 0.341814 0.651361 0.060 Uiso 1 1 calc R U . . . H9B H 0.516143 0.440769 0.685425 0.060 Uiso 1 1 calc R U . . . H9C H 0.586549 0.435719 0.619423 0.060 Uiso 1 1 calc R U . . . C10 C 0.3878(4) 0.3669(2) 0.54048(17) 0.0400(8) Uani 1 1 d . . . . . H10A H 0.300471 0.369355 0.514913 0.060 Uiso 1 1 calc R U . . . H10B H 0.412258 0.301457 0.549633 0.060 Uiso 1 1 calc R U . . . H10C H 0.455195 0.396134 0.515906 0.060 Uiso 1 1 calc R U . . . C11 C 0.4998(3) 0.7649(2) 0.63561(15) 0.0291(6) Uani 1 1 d . . . . . C12 C 0.6186(8) 0.7288(6) 0.6755(5) 0.058(2) Uani 0.5 1 d . . P A 1 H12A H 0.590163 0.689933 0.710677 0.087 Uiso 0.5 1 calc R U P A 1 H12B H 0.672155 0.781404 0.694025 0.087 Uiso 0.5 1 calc R U P A 1 H12C H 0.672473 0.691048 0.648294 0.087 Uiso 0.5 1 calc R U P A 1 C13 C 0.4232(8) 0.8323(7) 0.6757(5) 0.062(3) Uani 0.5 1 d . . P A 1 H13A H 0.378052 0.796810 0.707680 0.093 Uiso 0.5 1 calc R U P A 1 H13B H 0.356647 0.866296 0.646861 0.093 Uiso 0.5 1 calc R U P A 1 H13C H 0.485666 0.876922 0.698147 0.093 Uiso 0.5 1 calc R U P A 1 C14 C 0.5449(9) 0.8250(6) 0.5800(4) 0.057(2) Uani 0.5 1 d . . P A 1 H14A H 0.598752 0.877696 0.598154 0.086 Uiso 0.5 1 calc R U P A 1 H14B H 0.466189 0.848940 0.553366 0.086 Uiso 0.5 1 calc R U P A 1 H14C H 0.598462 0.786714 0.552989 0.086 Uiso 0.5 1 calc R U P A 1 C15 C 0.0720(3) 0.74385(19) 0.45925(16) 0.0304(6) Uani 1 1 d . . . . . H15A H 0.107869 0.800618 0.482264 0.037 Uiso 1 1 calc R U . . . H15B H -0.020848 0.757001 0.441059 0.037 Uiso 1 1 calc R U . . . C16 C 0.1566(3) 0.7199(2) 0.40482(15) 0.0311(6) Uani 1 1 d . . . . . H16A H 0.141795 0.766839 0.369640 0.037 Uiso 1 1 calc R U . . . H16B H 0.252436 0.721093 0.421312 0.037 Uiso 1 1 calc R U . . . C17 C 0.1514(3) 0.6029(2) 0.32302(15) 0.0284(6) Uani 1 1 d . . . . . H17 H 0.191667 0.649792 0.298814 0.034 Uiso 1 1 calc R U . . . C18 C 0.1311(3) 0.5120(2) 0.29258(15) 0.0274(6) Uani 1 1 d . . . . . C19 C 0.1731(3) 0.5029(2) 0.23032(15) 0.0319(6) Uani 1 1 d . . . . . H19 H 0.211187 0.555431 0.210777 0.038 Uiso 1 1 calc R U . . . C20 C 0.1606(3) 0.4203(2) 0.19712(15) 0.0334(7) Uani 1 1 d . . . . . C21 C 0.1033(3) 0.3418(2) 0.22394(15) 0.0319(6) Uani 1 1 d . . . . . H21 H 0.093257 0.284548 0.200629 0.038 Uiso 1 1 calc R U . . . C22 C 0.0622(3) 0.3502(2) 0.28494(15) 0.0289(6) Uani 1 1 d . . . . . C23 C 0.0763(3) 0.4332(2) 0.32348(14) 0.0261(6) Uani 1 1 d . . . . . C24 C 0.8953(5) 0.9537(4) 0.5721(3) 0.0714(14) Uani 1 1 d . . . . . H24A H 0.975366 0.945532 0.602632 0.107 Uiso 1 1 calc R U . . . H24B H 0.919200 0.985996 0.533122 0.107 Uiso 1 1 calc R U . . . H24C H 0.857106 0.892287 0.560091 0.107 Uiso 1 1 calc R U . . . C25 C 0.7937(4) 1.0113(3) 0.6039(2) 0.0562(11) Uani 1 1 d . . . . . C26 C 0.8005(4) 1.0220(3) 0.6693(2) 0.0571(11) Uani 1 1 d . . . . . H26 H 0.872245 0.994129 0.695829 0.069 Uiso 1 1 calc R U . . . C27 C 0.7038(6) 1.0735(4) 0.6984(3) 0.0733(14) Uani 1 1 d . . . . . H27 H 0.709676 1.081470 0.744203 0.088 Uiso 1 1 calc R U . . . C28 C 0.5974(5) 1.1133(3) 0.6578(3) 0.0695(14) Uani 1 1 d . . . . . H28 H 0.529526 1.148391 0.675639 0.083 Uiso 1 1 calc R U . . . C29 C 0.5944(5) 1.0999(3) 0.5923(3) 0.0682(14) Uani 1 1 d . . . . . H29 H 0.522507 1.125911 0.564814 0.082 Uiso 1 1 calc R U . . . C30 C 0.6899(5) 1.0512(3) 0.5648(3) 0.0666(13) Uani 1 1 d . . . . . H30 H 0.685325 1.044598 0.518971 0.080 Uiso 1 1 calc R U . . . C12A C 0.5214(10) 0.7473(6) 0.7099(3) 0.054(2) Uani 0.5 1 d . . P A 2 H12D H 0.583044 0.794350 0.730182 0.081 Uiso 0.5 1 calc R U P A 2 H12E H 0.559227 0.684688 0.718109 0.081 Uiso 0.5 1 calc R U P A 2 H12F H 0.435543 0.751729 0.728402 0.081 Uiso 0.5 1 calc R U P A 2 C13A C 0.4526(7) 0.8628(5) 0.6244(4) 0.0426(17) Uani 0.5 1 d . . P A 2 H13D H 0.448125 0.877220 0.577951 0.064 Uiso 0.5 1 calc R U P A 2 H13E H 0.514854 0.905942 0.648588 0.064 Uiso 0.5 1 calc R U P A 2 H13F H 0.363580 0.869704 0.639365 0.064 Uiso 0.5 1 calc R U P A 2 C14A C 0.6382(6) 0.7537(5) 0.6096(4) 0.0430(17) Uani 0.5 1 d . . P A 2 H14D H 0.628757 0.761037 0.562279 0.065 Uiso 0.5 1 calc R U P A 2 H14E H 0.674087 0.691345 0.620911 0.065 Uiso 0.5 1 calc R U P A 2 H14F H 0.699445 0.801503 0.629176 0.065 Uiso 0.5 1 calc R 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 Br1 0.0611(2) 0.02736(18) 0.0437(2) -0.00515(14) 0.00924(17) -0.01762(15) Zn1 0.02240(19) 0.01815(18) 0.0281(2) 0.00258(14) -0.00850(14) -0.00586(13) O1 0.0199(9) 0.0174(9) 0.0284(10) 0.0006(7) -0.0085(7) -0.0042(7) N1 0.0201(11) 0.0183(11) 0.0357(13) 0.0028(10) -0.0109(9) -0.0019(9) C1 0.0178(12) 0.0189(12) 0.0247(13) -0.0003(10) -0.0039(10) -0.0045(10) Br2 0.0537(2) 0.0515(2) 0.0400(2) -0.00374(16) 0.01181(16) -0.01002(18) O2 0.0342(11) 0.0216(10) 0.0314(11) -0.0012(8) 0.0001(8) -0.0075(8) N2 0.0251(12) 0.0209(11) 0.0340(13) 0.0046(10) -0.0088(10) -0.0064(9) C2 0.0183(12) 0.0202(12) 0.0222(12) 0.0018(10) -0.0029(10) -0.0007(10) C3 0.0161(12) 0.0264(14) 0.0247(13) 0.0005(11) -0.0048(10) -0.0019(10) C4 0.0193(12) 0.0233(13) 0.0244(13) -0.0037(10) -0.0032(10) -0.0051(10) C5 0.0237(13) 0.0176(12) 0.0296(14) -0.0005(11) -0.0033(11) -0.0023(10) C6 0.0166(12) 0.0214(13) 0.0279(13) 0.0006(10) -0.0060(10) -0.0012(10) C7 0.0218(13) 0.0227(14) 0.0318(15) 0.0036(11) -0.0062(11) 0.0007(11) C8 0.0317(15) 0.0304(16) 0.0442(18) 0.0134(14) -0.0033(13) -0.0031(13) C9 0.0268(16) 0.0305(16) 0.059(2) 0.0112(15) -0.0166(15) 0.0020(13) C10 0.0470(19) 0.0280(16) 0.0437(19) -0.0047(14) -0.0019(15) 0.0116(14) C11 0.0248(14) 0.0280(15) 0.0330(15) -0.0075(12) -0.0048(12) -0.0079(12) C12 0.042(4) 0.038(4) 0.085(6) -0.007(4) -0.038(4) -0.007(3) C13 0.040(4) 0.063(5) 0.080(7) -0.046(5) -0.004(4) -0.004(4) C14 0.062(5) 0.047(5) 0.060(5) 0.000(4) -0.007(4) -0.035(4) C15 0.0304(15) 0.0160(13) 0.0414(17) 0.0038(12) -0.0139(13) -0.0012(11) C16 0.0343(15) 0.0180(13) 0.0384(16) 0.0067(12) -0.0091(12) -0.0094(11) C17 0.0215(13) 0.0250(14) 0.0368(16) 0.0103(12) -0.0072(11) -0.0052(11) C18 0.0201(13) 0.0266(14) 0.0336(15) 0.0032(12) -0.0073(11) -0.0033(11) C19 0.0251(14) 0.0339(16) 0.0356(16) 0.0066(13) -0.0033(12) -0.0055(12) C20 0.0273(15) 0.0407(18) 0.0316(15) 0.0028(13) 0.0000(12) -0.0017(13) C21 0.0287(15) 0.0308(15) 0.0346(16) -0.0022(12) -0.0048(12) -0.0013(12) C22 0.0270(14) 0.0247(14) 0.0337(15) 0.0024(12) -0.0041(11) -0.0060(11) C23 0.0193(12) 0.0246(14) 0.0326(14) 0.0017(11) -0.0066(11) -0.0025(10) C24 0.067(3) 0.084(4) 0.064(3) 0.014(3) 0.007(2) -0.007(3) C25 0.055(2) 0.045(2) 0.067(3) 0.015(2) 0.000(2) -0.0180(19) C26 0.045(2) 0.049(2) 0.075(3) 0.018(2) -0.005(2) -0.0126(18) C27 0.074(3) 0.058(3) 0.088(4) 0.008(3) 0.010(3) -0.025(3) C28 0.054(3) 0.045(2) 0.109(4) 0.008(3) 0.008(3) -0.009(2) C29 0.055(3) 0.045(2) 0.101(4) 0.016(3) -0.004(3) -0.011(2) C30 0.061(3) 0.048(2) 0.088(3) 0.018(2) -0.011(2) -0.019(2) C12A 0.074(6) 0.056(5) 0.028(3) -0.010(3) -0.013(3) -0.028(4) C13A 0.035(3) 0.028(3) 0.062(5) -0.016(3) -0.009(3) -0.010(3) C14A 0.023(3) 0.041(4) 0.064(5) -0.017(3) 0.002(3) -0.016(3) 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' 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' Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 O2 Zn1 O1 97.56(8) . 3_566 ? O2 Zn1 N2 91.84(10) . . ? O1 Zn1 N2 137.30(9) 3_566 . ? O2 Zn1 O1 102.24(8) . . ? O1 Zn1 O1 92.31(7) 3_566 . ? N2 Zn1 O1 126.22(9) . . ? O2 Zn1 N1 170.68(9) . . ? O1 Zn1 N1 91.72(8) 3_566 . ? N2 Zn1 N1 80.68(10) . . ? O1 Zn1 N1 78.14(8) . . ? O2 Zn1 Zn1 104.38(6) . 3_566 ? O1 Zn1 Zn1 46.52(5) 3_566 3_566 ? N2 Zn1 Zn1 162.99(7) . 3_566 ? O1 Zn1 Zn1 45.79(6) . 3_566 ? N1 Zn1 Zn1 82.66(7) . 3_566 ? C1 O1 Zn1 122.64(17) . 3_566 ? C1 O1 Zn1 109.34(16) . . ? Zn1 O1 Zn1 87.69(7) 3_566 . ? C6 N1 C15 117.0(2) . . ? C6 N1 Zn1 102.64(17) . . ? C15 N1 Zn1 104.69(18) . . ? C6 N1 H1 110.6 . . ? C15 N1 H1 110.6 . . ? Zn1 N1 H1 110.6 . . ? O1 C1 C6 118.9(2) . . ? O1 C1 C2 121.9(2) . . ? C6 C1 C2 119.2(2) . . ? C23 O2 Zn1 127.92(19) . . ? C17 N2 C16 119.3(3) . . ? C17 N2 Zn1 125.3(2) . . ? C16 N2 Zn1 115.1(2) . . ? C3 C2 C1 117.2(2) . . ? C3 C2 C7 121.3(2) . . ? C1 C2 C7 121.5(2) . . ? C4 C3 C2 124.2(2) . . ? C4 C3 H3 117.9 . . ? C2 C3 H3 117.9 . . ? C3 C4 C5 117.2(2) . . ? C3 C4 C11 121.5(2) . . ? C5 C4 C11 121.4(3) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 121.8(2) . . ? C5 C6 N1 122.8(2) . . ? C1 C6 N1 115.4(2) . . ? C10 C7 C9 107.0(3) . . ? C10 C7 C8 110.2(3) . . ? C9 C7 C8 107.7(3) . . ? C10 C7 C2 110.2(2) . . ? C9 C7 C2 111.8(2) . . ? C8 C7 C2 109.7(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C13 109.9(6) . . ? C12 C11 C4 114.9(4) . . ? C13A C11 C4 114.7(3) . . ? C13 C11 C4 109.1(4) . . ? C12 C11 C14 109.3(6) . . ? C13 C11 C14 104.8(6) . . ? C4 C11 C14 108.2(4) . . ? C13A C11 C14A 109.1(5) . . ? C4 C11 C14A 109.9(3) . . ? C13A C11 C12A 108.5(5) . . ? C4 C11 C12A 107.7(4) . . ? C14A C11 C12A 106.5(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 C16 109.6(2) . . ? N1 C15 H15A 109.7 . . ? C16 C15 H15A 109.7 . . ? N1 C15 H15B 109.7 . . ? C16 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? N2 C16 C15 109.5(2) . . ? N2 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? N2 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? N2 C17 C18 126.3(3) . . ? N2 C17 H17 116.8 . . ? C18 C17 H17 116.8 . . ? C19 C18 C23 120.2(3) . . ? C19 C18 C17 116.1(3) . . ? C23 C18 C17 123.7(3) . . ? C20 C19 C18 121.4(3) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C19 C20 C21 120.9(3) . . ? C19 C20 Br2 120.6(2) . . ? C21 C20 Br2 118.4(3) . . ? C22 C21 C20 117.9(3) . . ? C22 C21 H21 121.1 . . ? C20 C21 H21 121.1 . . ? C21 C22 C23 124.4(3) . . ? C21 C22 Br1 118.6(2) . . ? C23 C22 Br1 117.0(2) . . ? O2 C23 C22 120.0(3) . . ? O2 C23 C18 124.9(3) . . ? C22 C23 C18 115.1(3) . . ? C25 C24 H24A 109.5 . . ? C25 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C25 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C30 119.9(5) . . ? C26 C25 C24 121.6(4) . . ? C30 C25 C24 118.4(5) . . ? C25 C26 C27 121.2(5) . . ? C25 C26 H26 119.4 . . ? C27 C26 H26 119.4 . . ? C26 C27 C28 118.2(5) . . ? C26 C27 H27 120.9 . . ? C28 C27 H27 120.9 . . ? C29 C28 C27 118.4(5) . . ? C29 C28 H28 120.8 . . ? C27 C28 H28 120.8 . . ? C30 C29 C28 122.7(5) . . ? C30 C29 H29 118.6 . . ? C28 C29 H29 118.6 . . ? C29 C30 C25 119.6(6) . . ? C29 C30 H30 120.2 . . ? C25 C30 H30 120.2 . . ? C11 C12A H12D 109.5 . . ? C11 C12A H12E 109.5 . . ? H12D C12A H12E 109.5 . . ? C11 C12A H12F 109.5 . . ? H12D C12A H12F 109.5 . . ? H12E C12A H12F 109.5 . . ? C11 C13A H13D 109.5 . . ? C11 C13A H13E 109.5 . . ? H13D C13A H13E 109.5 . . ? C11 C13A H13F 109.5 . . ? H13D C13A H13F 109.5 . . ? H13E C13A H13F 109.5 . . ? C11 C14A H14D 109.5 . . ? C11 C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? C11 C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? 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 Br1 C22 1.888(3) . ? Zn1 O2 1.972(2) . ? Zn1 O1 2.021(2) 3_566 ? Zn1 N2 2.026(3) . ? Zn1 O1 2.0453(18) . ? Zn1 N1 2.212(2) . ? Zn1 Zn1 2.8166(8) 3_566 ? O1 C1 1.366(3) . ? N1 C6 1.455(3) . ? N1 C15 1.474(4) . ? N1 H1 1.0000 . ? C1 C6 1.399(4) . ? C1 C2 1.408(4) . ? Br2 C20 1.903(3) . ? O2 C23 1.291(4) . ? N2 C17 1.279(4) . ? N2 C16 1.470(4) . ? C2 C3 1.397(4) . ? C2 C7 1.536(4) . ? C3 C4 1.392(4) . ? C3 H3 0.9500 . ? C4 C5 1.395(4) . ? C4 C11 1.535(4) . ? C5 C6 1.381(4) . ? C5 H5 0.9500 . ? C7 C10 1.528(4) . ? C7 C9 1.533(4) . ? C7 C8 1.536(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.477(8) . ? C11 C13A 1.487(8) . ? C11 C13 1.527(8) . ? C11 C14 1.539(9) . ? C11 C14A 1.549(7) . ? C11 C12A 1.552(8) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.516(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.450(4) . ? C17 H17 0.9500 . ? C18 C19 1.400(4) . ? C18 C23 1.430(4) . ? C19 C20 1.365(5) . ? C19 H19 0.9500 . ? C20 C21 1.399(5) . ? C21 C22 1.371(5) . ? C21 H21 0.9500 . ? C22 C23 1.428(4) . ? C24 C25 1.511(7) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.357(7) . ? C25 C30 1.379(7) . ? C26 C27 1.402(8) . ? C26 H26 0.9500 . ? C27 C28 1.413(8) . ? C27 H27 0.9500 . ? C28 C29 1.367(8) . ? C28 H28 0.9500 . ? C29 C30 1.354(8) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C12A H12D 0.9800 . ? C12A H12E 0.9800 . ? C12A H12F 0.9800 . ? C13A H13D 0.9800 . ? C13A H13E 0.9800 . ? C13A H13F 0.9800 . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ?