#------------------------------------------------------------------------------ #$Date: 2020-05-14 06:08:43 +0300 (Thu, 14 May 2020) $ #$Revision: 252047 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240533.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_7240533 loop_ _publ_author_name 'Podjed, Nina' 'Modec, Barbara' 'Alcaide, Mar\'ia M.' 'L\'opez-Serrano, Joaqu\'in' _publ_section_title ; From cyclic amines and acetonitrile to amidine zinc(ii) complexes ; _journal_issue 31 _journal_name_full 'RSC Advances' _journal_page_first 18200 _journal_paper_doi 10.1039/D0RA03192E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C26 H24 N4 O4 Zn, 2(C H Cl3)' _chemical_formula_sum 'C28 H26 Cl6 N4 O4 Zn' _chemical_formula_weight 760.60 _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' _atom_sites_solution_hydrogens mixed _audit_creation_date 2019-12-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-12-19 deposited with the CCDC. 2020-04-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.780(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.2026(3) _cell_length_b 20.3546(5) _cell_length_c 15.8428(5) _cell_measurement_reflns_used 13275 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 29.5850 _cell_measurement_theta_min 2.7080 _cell_volume 3259.79(16) _computing_cell_refinement 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46e (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 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 150.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.4933 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -48.00 65.00 1.00 32.50 -- -14.21 77.00 120.00 113 2 \w -19.00 93.00 1.00 32.50 -- 14.36 77.00-150.00 112 3 \w -19.00 93.00 1.00 32.50 -- 14.36 77.00 -30.00 112 4 \w -12.00 42.00 1.00 32.50 -- 14.36 37.00 120.00 54 5 \w 34.00 103.00 1.00 32.50 -- 14.36-178.00 30.00 69 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0043317000 _diffrn_orient_matrix_UB_12 0.0337678000 _diffrn_orient_matrix_UB_13 0.0103163000 _diffrn_orient_matrix_UB_21 0.0245611000 _diffrn_orient_matrix_UB_22 0.0085413000 _diffrn_orient_matrix_UB_23 -0.0383374000 _diffrn_orient_matrix_UB_31 -0.0655893000 _diffrn_orient_matrix_UB_32 0.0009758000 _diffrn_orient_matrix_UB_33 -0.0215808000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_unetI/netI 0.0254 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 38010 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_min 2.385 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.285 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.37186 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1544 _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.983 _refine_diff_density_min -1.218 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 458 _refine_ls_number_reflns 7490 _refine_ls_number_restraints 36 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0430 _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^)+(0.0417P)^2^+4.0939P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1003 _refine_ls_wR_factor_ref 0.1082 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6163 _reflns_number_total 7490 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03192e3.cif _cod_data_source_block 10b _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7240533 _shelx_shelxl_version_number 2018/3 _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_estimated_absorpt_t_max 0.831 _shelx_estimated_absorpt_t_min 0.360 _shelx_res_file ; TITL mob534_a.res in P2(1)/n mob534.res created by SHELXL-2018/3 at 11:25:21 on 16-Dec-2019 CELL 0.71073 10.2026 20.3546 15.8428 90 97.78 90 ZERR 4 0.0003 0.0005 0.0005 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O Zn UNIT 112 104 24 16 16 4 EQIV $1 2-X,1-Y,1-Z DELU 0.005 0.005 Cl1 > Cl6 DELU 0.005 0.005 Cl8 > Cl9A SIMU 0.01 0.02 2 Cl1 > Cl6 SIMU 0.01 0.02 2 Cl8 > Cl9A L.S. 10 PLAN 10 SIZE 1 0.2 0.15 MPLA N1 C11 C12 C13 C14 C15 C16 C17 C18 C19 MPLA N2 C21 C22 C23 C24 C25 C26 C27 C28 C29 HTAB N32 O12_$1 BOND $H htab LIST 6 fmap 2 acta MERG 2 SHEL 30 0.7696 REM REM REM WGHT 0.041700 4.093900 FVAR 2.45917 0.56095 0.53230 0.37258 ZN1 6 0.776578 0.509729 0.318378 11.00000 0.02643 0.02696 = 0.02574 -0.00187 0.00309 0.00003 N1 4 0.709196 0.472240 0.433642 11.00000 0.03167 0.02945 = 0.02687 0.00109 0.00480 0.00675 N2 4 0.804185 0.580897 0.219594 11.00000 0.02232 0.02684 = 0.02756 -0.00040 0.00271 0.00014 O11 5 0.879140 0.566338 0.407423 11.00000 0.04012 0.03207 = 0.03243 -0.00462 -0.00141 -0.00407 O12 5 0.932150 0.582450 0.546954 11.00000 0.06274 0.04876 = 0.03723 -0.00997 -0.01752 0.00287 O21 5 0.588710 0.528416 0.268246 11.00000 0.02529 0.04044 = 0.03798 0.00368 0.00682 -0.00177 O22 5 0.458715 0.593681 0.180787 11.00000 0.02160 0.05454 = 0.08371 0.01818 0.00193 0.00595 C11 1 0.765745 0.504237 0.501294 11.00000 0.03859 0.03287 = 0.02589 0.00158 -0.00010 0.01608 C12 1 0.728651 0.495576 0.583129 11.00000 0.05341 0.04997 = 0.02411 0.00295 0.00026 0.02376 AFIX 43 H12 2 0.773111 0.517712 0.629810 11.00000 -1.20000 AFIX 0 C13 1 0.627107 0.454453 0.592691 11.00000 0.05517 0.06049 = 0.02949 0.01857 0.01549 0.03130 AFIX 43 H13 2 0.598811 0.449713 0.645747 11.00000 -1.20000 AFIX 0 C14 1 0.564635 0.418986 0.522341 11.00000 0.03949 0.03973 = 0.04285 0.01965 0.01721 0.02167 C15 1 0.457017 0.375929 0.526567 11.00000 0.04853 0.04656 = 0.06532 0.03238 0.03025 0.02225 AFIX 43 H15 2 0.423435 0.370546 0.577851 11.00000 -1.20000 AFIX 0 C16 1 0.402114 0.342316 0.456458 11.00000 0.04305 0.03777 = 0.08876 0.02592 0.02660 0.00593 AFIX 43 H16 2 0.331490 0.314082 0.460270 11.00000 -1.20000 AFIX 0 C17 1 0.451128 0.349833 0.378138 11.00000 0.04477 0.03750 = 0.06751 0.00678 0.01121 -0.00405 AFIX 43 H17 2 0.414001 0.325798 0.330957 11.00000 -1.20000 AFIX 0 C18 1 0.553005 0.392255 0.370963 11.00000 0.04272 0.03373 = 0.04501 0.00458 0.01269 -0.00228 AFIX 43 H18 2 0.583957 0.397444 0.318785 11.00000 -1.20000 AFIX 0 C19 1 0.611091 0.428068 0.442356 11.00000 0.03336 0.03154 = 0.03555 0.00822 0.01008 0.01000 C110 1 0.868813 0.554738 0.485626 11.00000 0.03959 0.03148 = 0.03239 -0.00437 -0.00541 0.01137 C21 1 0.689221 0.603194 0.181927 11.00000 0.02417 0.03245 = 0.03280 0.00133 0.00134 0.00244 C22 1 0.678245 0.650274 0.116766 11.00000 0.03220 0.05030 = 0.04792 0.01729 -0.00119 0.00744 AFIX 43 H22 2 0.595681 0.665799 0.093053 11.00000 -1.20000 AFIX 0 C23 1 0.790105 0.672901 0.088754 11.00000 0.04697 0.04908 = 0.04241 0.02004 0.00361 0.00032 AFIX 43 H23 2 0.784396 0.703736 0.045092 11.00000 -1.20000 AFIX 0 C24 1 0.914280 0.649653 0.125828 11.00000 0.03506 0.03712 = 0.03159 0.00043 0.00581 -0.00542 C25 1 1.035717 0.669243 0.098798 11.00000 0.04849 0.04697 = 0.03841 0.00085 0.01289 -0.01659 AFIX 43 H25 2 1.035174 0.698720 0.053901 11.00000 -1.20000 AFIX 0 C26 1 1.151986 0.645353 0.137856 11.00000 0.03234 0.06326 = 0.04999 -0.00674 0.01495 -0.01831 AFIX 43 H26 2 1.230598 0.657780 0.118729 11.00000 -1.20000 AFIX 0 C27 1 1.155224 0.602064 0.206853 11.00000 0.02481 0.06171 = 0.05095 -0.00493 0.00412 -0.00415 AFIX 43 H27 2 1.236167 0.587295 0.234365 11.00000 -1.20000 AFIX 0 C28 1 1.040874 0.581338 0.234122 11.00000 0.02526 0.04460 = 0.03862 0.00247 0.00361 -0.00097 AFIX 43 H28 2 1.043990 0.552373 0.279748 11.00000 -1.20000 AFIX 0 C29 1 0.918421 0.603874 0.193086 11.00000 0.02406 0.03027 = 0.02841 -0.00434 0.00408 -0.00337 C210 1 0.567603 0.573380 0.212340 11.00000 0.02241 0.03564 = 0.04285 -0.00095 0.00368 0.00184 N31 4 0.949945 0.342625 0.218637 11.00000 0.03976 0.03597 = 0.03702 -0.01235 -0.00148 0.00803 N32 4 0.875117 0.430705 0.291382 11.00000 0.03328 0.02907 = 0.02232 0.00063 0.00055 0.00499 H32 2 0.926286 0.417331 0.332503 11.00000 0.04202 C31 1 1.035237 0.317447 0.292476 11.00000 0.08977 0.05249 = 0.08202 -0.02745 -0.04489 0.04177 AFIX 23 H31A 2 0.983945 0.304562 0.337030 11.00000 -1.20000 H31B 2 1.099944 0.350096 0.314983 11.00000 -1.20000 AFIX 0 C32 1 1.102081 0.258327 0.258294 11.00000 0.08542 0.05454 = 0.14537 -0.03755 -0.03172 0.03918 PART 1 AFIX 23 H32A 2 1.058377 0.217851 0.270815 21.00000 -1.20000 H32B 2 1.194541 0.255923 0.282441 21.00000 -1.20000 AFIX 23 PART 0 PART 2 H32C 2 1.186182 0.271019 0.241065 -21.00000 -1.20000 H32D 2 1.118102 0.224686 0.301834 -21.00000 -1.20000 AFIX 0 PART 0 PART 1 C33 1 1.085890 0.272202 0.151613 21.00000 0.04372 0.05218 = 0.09570 -0.04562 0.01253 0.00087 AFIX 23 H33A 2 1.154681 0.300895 0.136091 21.00000 -1.20000 H33B 2 1.084524 0.231668 0.119308 21.00000 -1.20000 AFIX 0 PART 0 PART 2 C33A 1 1.020272 0.235457 0.190946 -21.00000 0.06906 0.04814 = 0.07548 -0.02774 -0.00382 0.02021 AFIX 23 H33C 2 0.950063 0.209059 0.209148 -21.00000 -1.20000 H33D 2 1.068055 0.209264 0.154043 -21.00000 -1.20000 AFIX 0 PART 0 C34 1 0.960199 0.303500 0.141931 11.00000 0.06991 0.06234 = 0.06081 -0.03598 0.00492 0.01322 PART 1 AFIX 23 H34A 2 0.890451 0.270792 0.134326 21.00000 -1.20000 H34B 2 0.950771 0.331710 0.092130 21.00000 -1.20000 AFIX 23 PART 0 PART 2 H34C 2 1.021009 0.322691 0.106794 -21.00000 -1.20000 H34D 2 0.874808 0.296338 0.108116 -21.00000 -1.20000 AFIX 0 PART 0 C35 1 0.876092 0.396330 0.222687 11.00000 0.03480 0.03082 = 0.02673 -0.00123 0.00064 0.00084 C36 1 0.792564 0.417140 0.142522 11.00000 0.10655 0.05995 = 0.03890 -0.01559 -0.02877 0.03517 AFIX 137 H36A 2 0.740404 0.454565 0.153855 11.00000 -1.50000 H36B 2 0.735139 0.381702 0.121511 11.00000 -1.50000 H36C 2 0.848401 0.428545 0.100616 11.00000 -1.50000 AFIX 0 C4 1 0.691689 0.533884 0.885477 11.00000 0.07507 0.06776 = 0.09505 -0.03234 -0.01465 -0.00137 PART 1 CL1 3 0.786310 0.572549 0.798257 31.00000 0.11084 0.06846 = 0.07130 -0.00305 0.02908 -0.01520 CL2 3 0.578948 0.597286 0.891141 31.00000 0.06826 0.09436 = 0.13296 -0.05464 -0.00123 0.02297 CL3 3 0.808219 0.523878 0.964358 31.00000 0.20157 0.12448 = 0.05403 -0.00610 -0.01457 0.09688 PART 0 PART 2 CL4 3 0.665229 0.583262 0.817732 -31.00000 0.18952 0.17825 = 0.18084 0.12652 -0.11762 -0.11560 CL5 3 0.569305 0.528037 0.966195 -31.00000 0.07035 0.27913 = 0.08149 -0.07085 0.00282 -0.00697 CL6 3 0.844700 0.531971 0.952191 -31.00000 0.05470 0.08934 = 0.08815 -0.01879 -0.00815 -0.02188 PART 0 C5 1 0.966353 0.711176 0.404756 11.00000 0.08652 0.05007 = 0.08360 -0.02388 0.02443 -0.03457 CL7 3 0.906464 0.756327 0.486110 11.00000 0.05856 0.06116 = 0.04969 -0.00147 0.00306 -0.01400 PART 1 CL8 3 1.149040 0.689662 0.455105 41.00000 0.04582 0.06788 = 0.18935 -0.04856 0.01532 -0.01155 CL9 3 0.971734 0.743636 0.315572 41.00000 0.20513 0.04993 = 0.06722 -0.00540 0.05354 -0.01337 PART 0 PART 2 CL8A 3 1.126607 0.716959 0.404111 -41.00000 0.06618 0.11377 = 0.17334 -0.07457 0.03248 -0.03167 CL9A 3 0.877880 0.747892 0.304240 -41.00000 0.15871 0.06247 = 0.05083 -0.01481 0.00566 0.01162 PART 0 H5 2 0.938089 0.670290 0.403299 11.00000 0.05695 H4 2 0.662711 0.494365 0.864685 11.00000 0.08047 HKLF 4 REM mob534_a.res in P2(1)/n REM wR2 = 0.1082, GooF = S = 1.027, Restrained GooF = 1.067 for all data REM R1 = 0.0430 for 6163 Fo > 4sig(Fo) and 0.0550 for all 7490 data REM 458 parameters refined using 36 restraints END WGHT 0.0417 4.0938 REM Instructions for potential hydrogen bonds HTAB C12 Cl1 EQIV $3 x-1/2, -y+3/2, z-1/2 HTAB C22 Cl7_$3 HTAB N32 O12_$1 HTAB C31 O12_$1 HTAB C31 Cl1_$1 EQIV $4 -x+3/2, y-1/2, -z+1/2 HTAB C32 O22_$4 HTAB C33 Cl1_$1 EQIV $5 x, y, z-1 HTAB C36 Cl3_$5 HTAB C5 O11 EQIV $6 -x+1, -y+1, -z+1 HTAB C4 O22_$6 REM Highest difference peak 0.983, deepest hole -1.218, 1-sigma level 0.064 Q1 1 0.6260 0.6100 0.8569 11.00000 0.05 0.98 Q2 1 0.6902 0.5724 0.8042 11.00000 0.05 0.86 Q3 1 0.5881 0.5030 0.9716 11.00000 0.05 0.71 Q4 1 0.5764 0.5616 0.9309 11.00000 0.05 0.65 Q5 1 0.5391 0.5999 0.8818 11.00000 0.05 0.61 Q6 1 0.8133 0.5365 0.9004 11.00000 0.05 0.45 Q7 1 0.8044 0.7240 0.3225 11.00000 0.05 0.41 Q8 1 0.5973 0.6103 0.9223 11.00000 0.05 0.39 Q9 1 0.7295 0.5014 0.9465 11.00000 0.05 0.34 Q10 1 0.8423 0.5657 0.8456 11.00000 0.05 0.31 ; _shelx_res_checksum 48130 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 Zn1 Zn 0.77658(3) 0.50973(2) 0.31838(2) 0.02642(8) Uani 1 1 d . . . . . N1 N 0.7092(2) 0.47224(10) 0.43364(13) 0.0293(4) Uani 1 1 d . . . . . N2 N 0.80418(18) 0.58090(9) 0.21959(12) 0.0256(4) Uani 1 1 d . . . . . O11 O 0.87914(18) 0.56634(9) 0.40742(11) 0.0355(4) Uani 1 1 d . . . . . O12 O 0.9322(2) 0.58245(11) 0.54695(13) 0.0518(5) Uani 1 1 d . . . . . O21 O 0.58871(16) 0.52842(9) 0.26825(11) 0.0343(4) Uani 1 1 d . . . . . O22 O 0.45871(18) 0.59368(11) 0.18079(16) 0.0538(6) Uani 1 1 d . . . . . C11 C 0.7657(3) 0.50424(12) 0.50129(15) 0.0329(5) Uani 1 1 d . . . . . C12 C 0.7287(3) 0.49558(15) 0.58313(17) 0.0430(7) Uani 1 1 d . . . . . H12 H 0.773111 0.517712 0.629810 0.052 Uiso 1 1 calc R . . . . C13 C 0.6271(3) 0.45445(16) 0.59269(18) 0.0475(8) Uani 1 1 d . . . . . H13 H 0.598811 0.449713 0.645747 0.057 Uiso 1 1 calc R . . . . C14 C 0.5646(3) 0.41899(13) 0.52234(18) 0.0396(6) Uani 1 1 d . . . . . C15 C 0.4570(3) 0.37593(15) 0.5266(2) 0.0514(8) Uani 1 1 d . . . . . H15 H 0.423435 0.370546 0.577851 0.062 Uiso 1 1 calc R . . . . C16 C 0.4021(3) 0.34232(15) 0.4565(2) 0.0549(9) Uani 1 1 d . . . . . H16 H 0.331490 0.314082 0.460270 0.066 Uiso 1 1 calc R . . . . C17 C 0.4511(3) 0.34983(15) 0.3781(2) 0.0496(7) Uani 1 1 d . . . . . H17 H 0.414001 0.325798 0.330957 0.060 Uiso 1 1 calc R . . . . C18 C 0.5530(3) 0.39226(13) 0.37096(19) 0.0399(6) Uani 1 1 d . . . . . H18 H 0.583957 0.397444 0.318785 0.048 Uiso 1 1 calc R . . . . C19 C 0.6111(2) 0.42807(12) 0.44236(16) 0.0330(5) Uani 1 1 d . . . . . C110 C 0.8688(3) 0.55474(13) 0.48563(16) 0.0354(6) Uani 1 1 d . . . . . C21 C 0.6892(2) 0.60319(12) 0.18193(16) 0.0300(5) Uani 1 1 d . . . . . C22 C 0.6782(3) 0.65027(15) 0.11677(19) 0.0441(7) Uani 1 1 d . . . . . H22 H 0.595681 0.665799 0.093053 0.053 Uiso 1 1 calc R . . . . C23 C 0.7901(3) 0.67290(15) 0.08875(19) 0.0464(7) Uani 1 1 d . . . . . H23 H 0.784396 0.703736 0.045092 0.056 Uiso 1 1 calc R . . . . C24 C 0.9143(2) 0.64965(13) 0.12583(16) 0.0345(5) Uani 1 1 d . . . . . C25 C 1.0357(3) 0.66924(15) 0.09880(18) 0.0440(7) Uani 1 1 d . . . . . H25 H 1.035174 0.698720 0.053901 0.053 Uiso 1 1 calc R . . . . C26 C 1.1520(3) 0.64535(16) 0.13786(19) 0.0477(7) Uani 1 1 d . . . . . H26 H 1.230598 0.657780 0.118729 0.057 Uiso 1 1 calc R . . . . C27 C 1.1552(3) 0.60206(16) 0.20685(19) 0.0459(7) Uani 1 1 d . . . . . H27 H 1.236167 0.587295 0.234365 0.055 Uiso 1 1 calc R . . . . C28 C 1.0409(2) 0.58134(14) 0.23412(17) 0.0362(6) Uani 1 1 d . . . . . H28 H 1.043990 0.552373 0.279748 0.043 Uiso 1 1 calc R . . . . C29 C 0.9184(2) 0.60387(12) 0.19309(15) 0.0275(5) Uani 1 1 d . . . . . C210 C 0.5676(2) 0.57338(13) 0.21234(17) 0.0337(5) Uani 1 1 d . . . . . N31 N 0.9499(2) 0.34263(11) 0.21864(14) 0.0382(5) Uani 1 1 d . . . . . N32 N 0.8751(2) 0.43070(10) 0.29138(13) 0.0285(4) Uani 1 1 d . . . . . H32 H 0.926(3) 0.4173(15) 0.333(2) 0.042(8) Uiso 1 1 d . . . . . C31 C 1.0352(4) 0.31745(18) 0.2925(3) 0.0800(14) Uani 1 1 d . . . . . H31A H 0.983945 0.304562 0.337030 0.096 Uiso 1 1 calc R . . . . H31B H 1.099944 0.350096 0.314983 0.096 Uiso 1 1 calc R . . . . C32 C 1.1021(5) 0.2583(2) 0.2583(4) 0.0995(18) Uani 1 1 d . . . . . H32A H 1.058377 0.217851 0.270815 0.119 Uiso 0.561(10) 1 calc R . P A 1 H32B H 1.194541 0.255923 0.282441 0.119 Uiso 0.561(10) 1 calc R . P A 1 H32C H 1.186182 0.271019 0.241065 0.119 Uiso 0.439(10) 1 calc R . P A 2 H32D H 1.118102 0.224686 0.301834 0.119 Uiso 0.439(10) 1 calc R . P A 2 C33 C 1.0859(6) 0.2722(3) 0.1516(5) 0.064(3) Uani 0.561(10) 1 d . . P A 1 H33A H 1.154681 0.300895 0.136091 0.076 Uiso 0.561(10) 1 calc R . P A 1 H33B H 1.084524 0.231668 0.119308 0.076 Uiso 0.561(10) 1 calc R . P A 1 C33A C 1.0203(10) 0.2355(4) 0.1909(6) 0.065(3) Uani 0.439(10) 1 d . . P A 2 H33C H 0.950063 0.209059 0.209148 0.079 Uiso 0.439(10) 1 calc R . P A 2 H33D H 1.068055 0.209264 0.154043 0.079 Uiso 0.439(10) 1 calc R . P A 2 C34 C 0.9602(4) 0.30350(18) 0.1419(2) 0.0647(10) Uani 1 1 d . . . . . H34A H 0.890451 0.270792 0.134326 0.078 Uiso 0.561(10) 1 calc R . P A 1 H34B H 0.950771 0.331710 0.092130 0.078 Uiso 0.561(10) 1 calc R . P A 1 H34C H 1.021009 0.322691 0.106794 0.078 Uiso 0.439(10) 1 calc R . P A 2 H34D H 0.874808 0.296338 0.108116 0.078 Uiso 0.439(10) 1 calc R . P A 2 C35 C 0.8761(2) 0.39633(12) 0.22269(15) 0.0311(5) Uani 1 1 d . . . . . C36 C 0.7926(4) 0.41714(19) 0.1425(2) 0.0720(12) Uani 1 1 d . . . . . H36A H 0.740404 0.454565 0.153855 0.108 Uiso 1 1 calc GR . . . . H36B H 0.735139 0.381702 0.121511 0.108 Uiso 1 1 calc GR . . . . H36C H 0.848401 0.428545 0.100616 0.108 Uiso 1 1 calc GR . . . . C4 C 0.6917(4) 0.5339(2) 0.8855(3) 0.0817(13) Uani 1 1 d . . . . . Cl1 Cl 0.7863(3) 0.57255(10) 0.79826(14) 0.0820(8) Uani 0.532(3) 1 d . U P B 1 Cl2 Cl 0.5789(2) 0.59729(13) 0.8911(2) 0.0999(11) Uani 0.532(3) 1 d . U P B 1 Cl3 Cl 0.8082(6) 0.5239(3) 0.9644(3) 0.130(2) Uani 0.532(3) 1 d . U P B 1 Cl4 Cl 0.6652(5) 0.5833(2) 0.8177(3) 0.196(3) Uani 0.468(3) 1 d . U P B 2 Cl5 Cl 0.5693(3) 0.5280(3) 0.9662(2) 0.144(2) Uani 0.468(3) 1 d . U P B 2 Cl6 Cl 0.8447(4) 0.5320(3) 0.9522(3) 0.0790(13) Uani 0.468(3) 1 d . U P B 2 C5 C 0.9664(4) 0.71118(19) 0.4048(3) 0.0722(12) Uani 1 1 d . . . . . Cl7 Cl 0.90646(8) 0.75633(4) 0.48611(5) 0.0569(2) Uani 1 1 d . . . . . Cl8 Cl 1.1490(4) 0.6897(3) 0.4551(8) 0.101(2) Uani 0.373(11) 1 d . U P C 1 Cl9 Cl 0.9717(15) 0.7436(2) 0.3156(4) 0.104(3) Uani 0.373(11) 1 d . U P C 1 Cl8A Cl 1.1266(4) 0.7170(3) 0.4041(4) 0.116(2) Uani 0.627(11) 1 d . U P C 2 Cl9A Cl 0.8779(7) 0.74789(13) 0.30424(15) 0.0915(12) Uani 0.627(11) 1 d . U P C 2 H5 H 0.938(3) 0.6703(18) 0.403(2) 0.057(10) Uiso 1 1 d . . . . . H4 H 0.663(4) 0.494(2) 0.865(3) 0.080(13) Uiso 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 Zn1 0.02643(14) 0.02696(14) 0.02574(15) -0.00187(10) 0.00309(10) 0.00003(10) N1 0.0317(10) 0.0295(10) 0.0269(10) 0.0011(8) 0.0048(8) 0.0067(8) N2 0.0223(9) 0.0268(9) 0.0276(10) -0.0004(8) 0.0027(7) 0.0001(7) O11 0.0401(10) 0.0321(9) 0.0324(10) -0.0046(7) -0.0014(7) -0.0041(7) O12 0.0627(13) 0.0488(12) 0.0372(11) -0.0100(9) -0.0175(9) 0.0029(10) O21 0.0253(8) 0.0404(10) 0.0380(10) 0.0037(8) 0.0068(7) -0.0018(7) O22 0.0216(9) 0.0545(13) 0.0837(16) 0.0182(11) 0.0019(9) 0.0060(8) C11 0.0386(13) 0.0329(13) 0.0259(12) 0.0016(10) -0.0001(10) 0.0161(10) C12 0.0534(17) 0.0500(17) 0.0241(13) 0.0029(11) 0.0003(11) 0.0238(13) C13 0.0552(17) 0.0605(19) 0.0295(14) 0.0186(13) 0.0155(12) 0.0313(15) C14 0.0395(14) 0.0397(14) 0.0429(15) 0.0197(12) 0.0172(12) 0.0217(11) C15 0.0485(17) 0.0466(17) 0.065(2) 0.0324(16) 0.0303(16) 0.0222(14) C16 0.0431(16) 0.0378(16) 0.089(3) 0.0259(17) 0.0266(17) 0.0059(13) C17 0.0448(16) 0.0375(15) 0.068(2) 0.0068(14) 0.0112(14) -0.0040(12) C18 0.0427(14) 0.0337(13) 0.0450(16) 0.0046(11) 0.0127(12) -0.0023(11) C19 0.0334(12) 0.0315(13) 0.0355(13) 0.0082(10) 0.0101(10) 0.0100(10) C110 0.0396(14) 0.0315(12) 0.0324(13) -0.0044(10) -0.0054(10) 0.0114(10) C21 0.0242(11) 0.0324(12) 0.0328(13) 0.0013(10) 0.0013(9) 0.0024(9) C22 0.0322(13) 0.0503(17) 0.0479(16) 0.0173(13) -0.0012(11) 0.0074(12) C23 0.0470(16) 0.0491(17) 0.0424(16) 0.0200(13) 0.0036(12) 0.0003(13) C24 0.0351(13) 0.0371(13) 0.0316(13) 0.0004(10) 0.0058(10) -0.0054(10) C25 0.0485(16) 0.0470(16) 0.0384(15) 0.0009(12) 0.0129(12) -0.0166(13) C26 0.0323(14) 0.0633(19) 0.0500(17) -0.0067(14) 0.0150(12) -0.0183(13) C27 0.0248(12) 0.0617(19) 0.0509(17) -0.0049(14) 0.0041(11) -0.0042(12) C28 0.0253(11) 0.0446(15) 0.0386(14) 0.0025(11) 0.0036(10) -0.0010(10) C29 0.0241(11) 0.0303(12) 0.0284(12) -0.0043(9) 0.0041(9) -0.0034(9) C210 0.0224(11) 0.0356(13) 0.0429(14) -0.0009(11) 0.0037(10) 0.0018(10) N31 0.0398(12) 0.0360(12) 0.0370(12) -0.0123(9) -0.0015(9) 0.0080(9) N32 0.0333(10) 0.0291(10) 0.0223(10) 0.0006(8) 0.0005(8) 0.0050(8) C31 0.090(3) 0.052(2) 0.082(3) -0.0274(19) -0.045(2) 0.042(2) C32 0.085(3) 0.055(2) 0.145(5) -0.038(3) -0.032(3) 0.039(2) C33 0.044(3) 0.052(4) 0.096(6) -0.046(4) 0.013(3) 0.001(3) C33A 0.069(6) 0.048(5) 0.075(6) -0.028(4) -0.004(4) 0.020(4) C34 0.070(2) 0.062(2) 0.061(2) -0.0360(18) 0.0049(17) 0.0132(17) C35 0.0348(12) 0.0308(12) 0.0267(12) -0.0012(9) 0.0006(9) 0.0008(10) C36 0.107(3) 0.060(2) 0.0389(18) -0.0156(15) -0.0288(18) 0.035(2) C4 0.075(3) 0.068(3) 0.095(3) -0.032(2) -0.015(2) -0.001(2) Cl1 0.1108(19) 0.0685(12) 0.0713(13) -0.0030(9) 0.0291(12) -0.0152(11) Cl2 0.0683(13) 0.0944(17) 0.133(2) -0.0546(17) -0.0012(13) 0.0230(11) Cl3 0.202(5) 0.124(3) 0.0540(15) -0.0061(19) -0.015(3) 0.097(3) Cl4 0.190(5) 0.178(4) 0.181(4) 0.127(3) -0.118(4) -0.116(4) Cl5 0.0704(17) 0.279(6) 0.081(2) -0.071(3) 0.0028(13) -0.007(2) Cl6 0.0547(13) 0.089(2) 0.088(3) -0.0188(17) -0.0081(13) -0.0219(14) C5 0.087(3) 0.050(2) 0.084(3) -0.0239(19) 0.024(2) -0.035(2) Cl7 0.0586(5) 0.0612(5) 0.0497(4) -0.0015(4) 0.0031(3) -0.0140(4) Cl8 0.0458(17) 0.068(3) 0.189(7) -0.049(3) 0.015(3) -0.0115(16) Cl9 0.205(9) 0.0499(18) 0.067(3) -0.0054(16) 0.054(4) -0.013(3) Cl8A 0.0662(16) 0.114(3) 0.173(4) -0.075(3) 0.032(2) -0.0317(19) Cl9A 0.159(4) 0.0625(11) 0.0508(10) -0.0148(8) 0.0057(14) 0.0116(16) 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' Cl Cl 0.1484 0.1585 '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' Zn Zn 0.2839 1.4301 '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 N1 Zn1 N2 157.34(7) . . ? O11 Zn1 N1 78.75(8) . . ? O11 Zn1 N2 91.00(7) . . ? O11 Zn1 O21 123.29(8) . . ? O21 Zn1 N1 90.30(7) . . ? O21 Zn1 N2 78.43(7) . . ? N32 Zn1 N1 97.13(8) . . ? N32 Zn1 N2 105.48(8) . . ? N32 Zn1 O11 112.86(8) . . ? N32 Zn1 O21 123.72(8) . . ? C11 N1 Zn1 110.85(17) . . ? C11 N1 C19 119.3(2) . . ? C19 N1 Zn1 129.41(17) . . ? C21 N2 Zn1 111.06(15) . . ? C21 N2 C29 118.9(2) . . ? C29 N2 Zn1 130.07(15) . . ? C110 O11 Zn1 118.17(16) . . ? C210 O21 Zn1 118.30(15) . . ? N1 C11 C12 122.9(3) . . ? N1 C11 C110 116.0(2) . . ? C12 C11 C110 120.9(2) . . ? C11 C12 H12 120.5 . . ? C13 C12 C11 119.0(3) . . ? C13 C12 H12 120.5 . . ? C12 C13 H13 120.0 . . ? C12 C13 C14 120.0(2) . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 123.5(3) . . ? C13 C14 C19 118.0(3) . . ? C15 C14 C19 118.5(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 119.7 . . ? C15 C16 C17 120.6(3) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 119.8 . . ? C18 C17 C16 120.4(3) . . ? C18 C17 H17 119.8 . . ? C17 C18 H18 119.9 . . ? C17 C18 C19 120.2(3) . . ? C19 C18 H18 119.9 . . ? N1 C19 C14 120.8(2) . . ? N1 C19 C18 119.6(2) . . ? C18 C19 C14 119.6(2) . . ? O11 C110 C11 115.7(2) . . ? O12 C110 O11 125.3(3) . . ? O12 C110 C11 119.0(2) . . ? N2 C21 C22 123.0(2) . . ? N2 C21 C210 115.7(2) . . ? C22 C21 C210 121.3(2) . . ? C21 C22 H22 120.5 . . ? C23 C22 C21 119.0(2) . . ? C23 C22 H22 120.5 . . ? C22 C23 H23 120.0 . . ? C22 C23 C24 119.9(3) . . ? C24 C23 H23 120.0 . . ? C23 C24 C25 123.6(3) . . ? C23 C24 C29 118.1(2) . . ? C29 C24 C25 118.3(2) . . ? C24 C25 H25 119.7 . . ? C26 C25 C24 120.5(3) . . ? C26 C25 H25 119.7 . . ? C25 C26 H26 119.7 . . ? C25 C26 C27 120.7(2) . . ? C27 C26 H26 119.7 . . ? C26 C27 H27 119.6 . . ? C28 C27 C26 120.7(3) . . ? C28 C27 H27 119.6 . . ? C27 C28 H28 120.1 . . ? C27 C28 C29 119.8(3) . . ? C29 C28 H28 120.1 . . ? N2 C29 C24 121.0(2) . . ? N2 C29 C28 119.1(2) . . ? C28 C29 C24 119.9(2) . . ? O21 C210 C21 116.1(2) . . ? O22 C210 O21 125.8(2) . . ? O22 C210 C21 118.1(2) . . ? C31 N31 C34 111.9(2) . . ? C35 N31 C31 122.1(2) . . ? C35 N31 C34 126.0(2) . . ? Zn1 N32 H32 113(2) . . ? C35 N32 Zn1 133.19(18) . . ? C35 N32 H32 114(2) . . ? N31 C31 H31A 111.0 . . ? N31 C31 H31B 111.0 . . ? N31 C31 C32 104.0(3) . . ? H31A C31 H31B 109.0 . . ? C32 C31 H31A 111.0 . . ? C32 C31 H31B 111.0 . . ? C31 C32 H32A 111.0 . . ? C31 C32 H32B 111.0 . . ? C31 C32 H32C 110.3 . . ? C31 C32 H32D 110.3 . . ? C31 C32 C33 103.6(4) . . ? H32A C32 H32B 109.0 . . ? H32C C32 H32D 108.5 . . ? C33 C32 H32A 111.0 . . ? C33 C32 H32B 111.0 . . ? C33A C32 C31 107.3(4) . . ? C33A C32 H32C 110.3 . . ? C33A C32 H32D 110.3 . . ? C32 C33 H33A 112.1 . . ? C32 C33 H33B 112.1 . . ? H33A C33 H33B 109.7 . . ? C34 C33 C32 98.4(4) . . ? C34 C33 H33A 112.1 . . ? C34 C33 H33B 112.1 . . ? C32 C33A H33C 111.1 . . ? C32 C33A H33D 111.1 . . ? C32 C33A C34 103.4(6) . . ? H33C C33A H33D 109.0 . . ? C34 C33A H33C 111.1 . . ? C34 C33A H33D 111.1 . . ? N31 C34 C33A 97.4(4) . . ? N31 C34 H34A 110.0 . . ? N31 C34 H34B 110.0 . . ? N31 C34 H34C 112.3 . . ? N31 C34 H34D 112.3 . . ? C33 C34 N31 108.5(4) . . ? C33 C34 H34A 110.0 . . ? C33 C34 H34B 110.0 . . ? C33A C34 H34C 112.3 . . ? C33A C34 H34D 112.3 . . ? H34A C34 H34B 108.4 . . ? H34C C34 H34D 109.9 . . ? N31 C35 C36 116.9(2) . . ? N32 C35 N31 123.5(2) . . ? N32 C35 C36 119.6(2) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36B 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? Cl1 C4 H4 106(3) . . ? Cl2 C4 Cl1 97.5(3) . . ? Cl2 C4 H4 120(3) . . ? Cl3 C4 Cl1 102.4(3) . . ? Cl3 C4 Cl2 118.4(3) . . ? Cl3 C4 H4 110(3) . . ? Cl4 C4 Cl5 117.4(4) . . ? Cl4 C4 Cl6 120.9(4) . . ? Cl4 C4 H4 109(3) . . ? Cl5 C4 H4 89(3) . . ? Cl6 C4 Cl5 101.7(3) . . ? Cl6 C4 H4 115(3) . . ? C4 Cl5 Cl5 151.5(4) . 3_667 ? Cl7 C5 Cl8 102.9(3) . . ? Cl7 C5 Cl9A 103.8(3) . . ? Cl7 C5 H5 112(2) . . ? Cl8 C5 H5 95(2) . . ? Cl9 C5 Cl7 119.9(4) . . ? Cl9 C5 Cl8 108.1(4) . . ? Cl9 C5 H5 115(2) . . ? Cl8A C5 Cl7 114.4(2) . . ? Cl8A C5 Cl9A 109.4(3) . . ? Cl8A C5 H5 113(2) . . ? Cl9A C5 H5 104(2) . . ? 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 Zn1 N1 2.175(2) . ? Zn1 N2 2.1786(19) . ? Zn1 O11 2.0033(17) . ? Zn1 O21 2.0093(17) . ? Zn1 N32 1.974(2) . ? N1 C11 1.318(3) . ? N1 C19 1.366(3) . ? N2 C21 1.322(3) . ? N2 C29 1.373(3) . ? O11 C110 1.280(3) . ? O12 C110 1.229(3) . ? O21 C210 1.272(3) . ? O22 C210 1.227(3) . ? C11 C12 1.410(4) . ? C11 C110 1.515(4) . ? C12 H12 0.9300 . ? C12 C13 1.356(5) . ? C13 H13 0.9300 . ? C13 C14 1.406(5) . ? C14 C15 1.414(4) . ? C14 C19 1.424(3) . ? C15 H15 0.9300 . ? C15 C16 1.359(5) . ? C16 H16 0.9300 . ? C16 C17 1.408(5) . ? C17 H17 0.9300 . ? C17 C18 1.368(4) . ? C18 H18 0.9300 . ? C18 C19 1.407(4) . ? C21 C22 1.402(4) . ? C21 C210 1.517(3) . ? C22 H22 0.9300 . ? C22 C23 1.360(4) . ? C23 H23 0.9300 . ? C23 C24 1.404(4) . ? C24 C25 1.422(4) . ? C24 C29 1.412(3) . ? C25 H25 0.9300 . ? C25 C26 1.352(4) . ? C26 H26 0.9300 . ? C26 C27 1.401(4) . ? C27 H27 0.9300 . ? C27 C28 1.365(4) . ? C28 H28 0.9300 . ? C28 C29 1.405(3) . ? N31 C31 1.454(4) . ? N31 C34 1.468(4) . ? N31 C35 1.334(3) . ? N32 H32 0.82(3) . ? N32 C35 1.295(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 C32 1.519(5) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 H32C 0.9700 . ? C32 H32D 0.9700 . ? C32 C33 1.699(10) . ? C32 C33A 1.346(9) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 C34 1.421(7) . ? C33A H33C 0.9700 . ? C33A H33D 0.9700 . ? C33A C34 1.664(10) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 H34C 0.9700 . ? C34 H34D 0.9700 . ? C35 C36 1.492(4) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C4 Cl1 1.955(6) . ? C4 Cl2 1.739(5) . ? C4 Cl3 1.617(6) . ? C4 Cl4 1.469(6) . ? C4 Cl5 1.908(6) . ? C4 Cl6 1.763(6) . ? C4 H4 0.90(4) . ? Cl5 Cl5 2.205(9) 3_667 ? C5 Cl7 1.759(4) . ? C5 Cl8 1.975(8) . ? C5 Cl9 1.567(7) . ? C5 Cl8A 1.641(5) . ? C5 Cl9A 1.876(6) . ? C5 H5 0.88(4) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N32 H32 O12 0.82(3) 2.23(3) 3.022(3) 161(3) 3_766 yes