#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:42:26 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258103 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240520.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_7240520 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_page_last 18221 _journal_paper_doi 10.1039/D0RA03192E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C27 H26 N4 O4 Zn, 2(C H Cl3)' _chemical_formula_sum 'C29 H28 Cl6 N4 O4 Zn' _chemical_formula_weight 774.62 _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 2019-12-17 _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 97.6380(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.23980(10) _cell_length_b 20.2129(2) _cell_length_c 16.02080(10) _cell_measurement_reflns_used 14056 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 75.0990 _cell_measurement_theta_min 3.4840 _cell_volume 3286.50(5) _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 1.000 _diffrn_measured_fraction_theta_max 0.990 _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 -116.00 -17.00 1.00 1.50 -- -41.76 -37.00 30.00 99 2 \w -66.00 33.00 1.00 1.50 -- -41.76 37.00-150.00 99 3 \w 23.00 98.00 1.00 1.50 -- 41.76-125.00-150.00 75 4 \w 80.00 178.00 1.00 6.00 -- 109.50 61.00-120.00 98 5 \w 27.00 109.00 1.00 6.00 -- 109.50 -94.00-150.00 82 6 \w 33.00 138.00 1.00 6.00 -- 109.50 -30.00 0.00 105 7 \w 94.00 178.00 1.00 6.00 -- 109.50 125.00-180.00 84 8 \w 37.00 139.00 1.00 6.00 -- 109.50 -61.00 90.00 102 9 \w 81.00 178.00 1.00 6.00 -- 109.50 30.00 0.00 97 10 \w 36.00 118.00 1.00 6.00 -- 109.50-125.00 150.00 82 11 \w 37.00 119.00 1.00 6.00 -- 109.50-127.00 97.00 82 12 \w 36.00 118.00 1.00 6.00 -- 109.50-125.00 -30.00 82 13 \w 27.00 109.00 1.00 6.00 -- 109.50 -94.00 90.00 82 14 \w 94.00 178.00 1.00 6.00 -- 109.50 125.00 60.00 84 15 \w -116.00 -17.00 1.00 1.50 -- -41.76 -37.00 150.00 99 16 \w -114.00 -14.00 1.00 1.50 -- -41.76 -57.00 -90.00 100 17 \w -30.00 70.00 1.00 1.50 -- 41.76 -57.00 -60.00 100 18 \w 81.00 106.00 1.00 6.00 -- 109.50 30.00 60.00 25 19 \w 84.00 178.00 1.00 6.00 -- 109.50 45.00 150.00 94 ; _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 -0.0352409000 _diffrn_orient_matrix_UB_12 -0.0543254000 _diffrn_orient_matrix_UB_13 -0.0666708000 _diffrn_orient_matrix_UB_21 -0.0235130000 _diffrn_orient_matrix_UB_22 0.0533155000 _diffrn_orient_matrix_UB_23 -0.0690826000 _diffrn_orient_matrix_UB_31 0.1457165000 _diffrn_orient_matrix_UB_32 -0.0045494000 _diffrn_orient_matrix_UB_33 -0.0138567000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_unetI/netI 0.0255 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 33472 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.403 _diffrn_reflns_theta_min 3.540 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 5.874 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.30445 _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 1.566 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1576 _exptl_crystal_size_max 0.7 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.388 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.054 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 491 _refine_ls_number_reflns 6741 _refine_ls_number_restraints 116 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0315 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0446P)^2^+1.2494P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0810 _refine_ls_wR_factor_ref 0.0859 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6008 _reflns_number_total 6741 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03192e3.cif _cod_data_source_block 4b _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 Adding full bibliography for 7240517--7240533.cif. ; _cod_database_code 7240520 _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 0.651 _shelx_estimated_absorpt_t_min 0.105 _shelx_res_file ; TITL Cua55 in P2(1)/n cua55.res created by SHELXL-2018/3 at 13:03:04 on 17-Dec-2019 CELL 1.54184 10.2398 20.2129 16.0208 90 97.638 90 ZERR 4 0.0001 0.0002 0.0001 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O Zn UNIT 116 112 24 16 16 4 EQIV $1 -X,-Y,-Z DELU 0.005 0.005 Cl5 > Cl8B SIMU 0.01 0.02 2 Cl5 > Cl8B SUMP 1 0.00001 1 2 1 3 1 4 1 5 L.S. 10 PLAN 10 SIZE 0.7 0.1 0.08 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 BOND fmap 2 acta MERG 2 REM REM REM WGHT 0.044600 1.249400 FVAR 3.57796 0.24530 0.27467 0.24457 0.23543 ZN1 6 0.216687 0.012014 0.177922 11.00000 0.02392 0.02545 = 0.02367 0.00094 0.00383 0.00141 O11 5 0.112819 0.068943 0.090741 11.00000 0.03468 0.03103 = 0.02642 0.00199 0.00376 0.00838 O12 5 0.065387 0.089823 -0.046494 11.00000 0.04058 0.04101 = 0.02884 0.00521 -0.00357 0.01067 O21 5 0.403359 0.032992 0.226701 11.00000 0.02150 0.04123 = 0.03618 -0.00291 0.00773 0.00179 O22 5 0.530030 0.098028 0.315980 11.00000 0.01898 0.05207 = 0.06816 -0.01038 0.00322 -0.00656 C11 1 0.230099 0.009433 -0.003585 11.00000 0.02563 0.02211 = 0.02489 -0.00198 0.00058 -0.00376 C12 1 0.267264 0.003152 -0.084499 11.00000 0.03138 0.03310 = 0.02260 -0.00098 -0.00070 -0.00456 AFIX 43 H12 2 0.224463 0.027319 -0.129426 11.00000 -1.20000 AFIX 0 C13 1 0.367570 -0.039165 -0.096007 11.00000 0.03314 0.03558 = 0.02363 -0.00821 0.00410 -0.00787 AFIX 43 H13 2 0.396708 -0.042609 -0.148397 11.00000 -1.20000 AFIX 0 C14 1 0.426263 -0.077466 -0.027699 11.00000 0.02687 0.02593 = 0.02922 -0.00715 0.00568 -0.00696 C15 1 0.530513 -0.122587 -0.034485 11.00000 0.03140 0.03019 = 0.03843 -0.01185 0.01145 -0.00429 AFIX 43 H15 2 0.562530 -0.127709 -0.085771 11.00000 -1.20000 AFIX 0 C16 1 0.583900 -0.158363 0.033404 11.00000 0.03144 0.02774 = 0.05088 -0.00702 0.01127 0.00432 AFIX 43 H16 2 0.652306 -0.187697 0.028161 11.00000 -1.20000 AFIX 0 C17 1 0.536557 -0.151465 0.111924 11.00000 0.03485 0.02987 = 0.04268 0.00469 0.00642 0.00492 AFIX 43 H17 2 0.572741 -0.176961 0.157537 11.00000 -1.20000 AFIX 0 C18 1 0.437711 -0.107465 0.121277 11.00000 0.03263 0.03130 = 0.03301 0.00251 0.00769 0.00368 AFIX 43 H18 2 0.408160 -0.102566 0.173366 11.00000 -1.20000 AFIX 0 C19 1 0.380784 -0.069588 0.051797 11.00000 0.02358 0.02287 = 0.02919 -0.00311 0.00493 -0.00308 C21 1 0.299540 0.101940 0.318214 11.00000 0.01975 0.02733 = 0.02873 0.00098 0.00166 -0.00372 C22 1 0.309318 0.143975 0.388427 11.00000 0.02586 0.03955 = 0.03224 -0.00515 -0.00063 -0.01089 AFIX 43 H22 2 0.391233 0.157641 0.414871 11.00000 -1.20000 AFIX 0 C23 1 0.196732 0.164395 0.417146 11.00000 0.03268 0.03685 = 0.03058 -0.00944 0.00184 -0.00600 AFIX 43 H23 2 0.201283 0.191555 0.464301 11.00000 -1.20000 AFIX 0 C24 1 0.073099 0.144327 0.375319 11.00000 0.02749 0.02675 = 0.02481 0.00009 0.00270 -0.00035 C25 1 -0.048041 0.163554 0.401515 11.00000 0.03361 0.03287 = 0.03174 -0.00232 0.00715 0.00490 AFIX 43 H25 2 -0.048249 0.189636 0.449318 11.00000 -1.20000 AFIX 0 C26 1 -0.164256 0.144032 0.357035 11.00000 0.02567 0.04189 = 0.04113 0.00057 0.00818 0.00846 AFIX 43 H26 2 -0.243467 0.156574 0.374831 11.00000 -1.20000 AFIX 0 C27 1 -0.165045 0.105098 0.284511 11.00000 0.02053 0.05393 = 0.03845 -0.00435 -0.00059 0.00088 AFIX 43 H27 2 -0.245163 0.093254 0.253819 11.00000 -1.20000 AFIX 0 C28 1 -0.050323 0.084194 0.258014 11.00000 0.02226 0.04485 = 0.03080 -0.00777 0.00083 -0.00111 AFIX 43 H28 2 -0.052578 0.057849 0.210253 11.00000 -1.20000 AFIX 0 C29 1 0.071473 0.102905 0.303696 11.00000 0.02112 0.02793 = 0.02434 -0.00032 0.00197 -0.00060 C31 1 0.028742 -0.203753 0.192173 11.00000 0.03965 0.02906 = 0.03122 -0.00217 0.00431 -0.00343 AFIX 23 H31A 2 0.060189 -0.248422 0.185208 11.00000 -1.20000 H31B 2 0.042930 -0.178281 0.142858 11.00000 -1.20000 AFIX 0 C32 1 -0.116576 -0.205217 0.200449 11.00000 0.03630 0.05484 = 0.03112 0.00112 -0.00488 -0.00913 AFIX 23 H32A 2 -0.164581 -0.226378 0.151334 11.00000 -1.20000 H32B 2 -0.149249 -0.160352 0.203453 11.00000 -1.20000 AFIX 0 C33 1 -0.139400 -0.243183 0.279797 11.00000 0.03746 0.06866 = 0.03861 0.00550 0.00176 -0.01930 AFIX 23 H33A 2 -0.231608 -0.240108 0.287416 11.00000 -1.20000 H33B 2 -0.118509 -0.289520 0.273031 11.00000 -1.20000 AFIX 0 C34 1 -0.054970 -0.215939 0.357375 11.00000 0.04147 0.04417 = 0.02914 0.00585 0.00269 -0.00353 AFIX 23 H34A 2 -0.085801 -0.172104 0.369778 11.00000 -1.20000 H34B 2 -0.063415 -0.244190 0.405308 11.00000 -1.20000 AFIX 0 C35 1 0.088749 -0.212281 0.343675 11.00000 0.03897 0.03573 = 0.03396 0.01265 -0.00567 -0.00588 AFIX 23 H35A 2 0.139876 -0.191666 0.392068 11.00000 -1.20000 H35B 2 0.122722 -0.256600 0.337833 11.00000 -1.20000 AFIX 0 C36 1 0.145386 -0.110779 0.269244 11.00000 0.02302 0.03137 = 0.02786 0.00245 0.00175 -0.00218 C37 1 0.221082 -0.085458 0.349490 11.00000 0.05274 0.04155 = 0.03314 0.00832 -0.01224 -0.01583 AFIX 137 H37A 2 0.265001 -0.045060 0.338428 11.00000 -1.50000 H37B 2 0.285166 -0.117809 0.371566 11.00000 -1.50000 H37C 2 0.161517 -0.077300 0.389827 11.00000 -1.50000 AFIX 0 C110 1 0.126450 0.060069 0.013342 11.00000 0.02698 0.02597 = 0.02868 0.00021 -0.00074 -0.00067 C210 1 0.422512 0.076078 0.284804 11.00000 0.01982 0.03353 = 0.03760 0.00414 0.00406 -0.00168 N1 4 0.284479 -0.024492 0.062234 11.00000 0.02545 0.02404 = 0.02318 -0.00032 0.00516 -0.00058 N2 4 0.185974 0.081722 0.277200 11.00000 0.01935 0.02559 = 0.02482 -0.00064 0.00193 -0.00113 N31 4 0.102018 -0.173816 0.267741 11.00000 0.03307 0.03194 = 0.02961 0.00656 -0.00274 -0.00621 N32 4 0.127573 -0.071028 0.204701 11.00000 0.02847 0.02909 = 0.02423 0.00097 0.00175 -0.00350 C4 1 0.015778 0.212607 0.091800 11.00000 0.03830 0.03358 = 0.03722 -0.00148 -0.00033 0.00989 AFIX 13 H4 2 0.059308 0.169334 0.094669 11.00000 -1.20000 AFIX 0 CL41 3 -0.153111 0.200737 0.059980 11.00000 0.03392 0.05992 = 0.06321 0.00595 0.00240 0.00619 CL42 3 0.045252 0.249815 0.192011 11.00000 0.07997 0.04776 = 0.03189 -0.00132 0.00489 0.00179 CL43 3 0.085260 0.262289 0.017819 11.00000 0.04033 0.05530 = 0.03297 -0.00012 0.00170 0.00120 C5 1 0.307958 0.026270 0.615130 11.00000 0.06964 0.05284 = 0.08179 0.02068 -0.02959 -0.00503 PART 1 CL5 3 0.156123 0.024585 0.562225 21.00000 0.07135 0.04727 = 0.06221 0.01473 -0.02014 0.00045 CL5A 3 0.438701 0.039175 0.546159 21.00000 0.07030 0.12620 = 0.08414 0.04148 -0.00019 -0.00707 CL5B 3 0.324971 0.074935 0.694489 21.00000 0.08422 0.05982 = 0.05802 -0.01672 -0.02193 0.01649 PART 0 PART 2 CL6 3 0.161915 0.029610 0.546049 31.00000 0.04326 0.04737 = 0.03568 0.00697 -0.01679 -0.00981 CL6A 3 0.428919 0.006656 0.527056 31.00000 0.06975 0.08714 = 0.06038 0.00790 0.00769 0.02023 CL6B 3 0.365977 0.097975 0.652354 31.00000 0.06896 0.06373 = 0.07925 -0.02352 -0.02052 0.01386 PART 0 PART 3 CL7 3 0.161315 0.018905 0.537902 41.00000 0.06933 0.05422 = 0.04283 -0.00413 -0.01827 -0.01173 CL7A 3 0.404403 0.093948 0.620178 41.00000 0.07418 0.05757 = 0.07524 0.00889 -0.00918 -0.02639 CL7B 3 0.255046 0.064416 0.710995 41.00000 0.12860 0.04966 = 0.04002 -0.00045 0.02234 0.02158 PART 0 PART 4 CL8 3 0.222827 0.005047 0.531112 51.00000 0.11273 0.07188 = 0.04262 -0.00422 0.00697 -0.03468 CL8A 3 0.420102 0.083228 0.583305 51.00000 0.06247 0.10787 = 0.08392 0.02940 -0.00459 -0.02194 CL8B 3 0.174853 0.055180 0.693301 51.00000 0.10944 0.05263 = 0.07480 0.01767 0.05203 0.03619 PART 0 H32 2 0.078039 -0.084680 0.161710 11.00000 0.03053 H5 2 0.336511 -0.011277 0.641657 11.00000 0.05501 HKLF 4 REM Cua55 in P2(1)/n REM wR2 = 0.0859, GooF = S = 1.039, Restrained GooF = 1.044 for all data REM R1 = 0.0315 for 6008 Fo > 4sig(Fo) and 0.0366 for all 6741 data REM 491 parameters refined using 116 restraints END WGHT 0.0446 1.2494 REM Instructions for potential hydrogen bonds EQIV $3 x, y, z-1 HTAB C12 Cl7B_$3 HTAB C12 Cl8B_$3 EQIV $4 x+1/2, -y+1/2, z+1/2 HTAB C22 Cl43_$4 HTAB C31 O12_$1 EQIV $5 -x, -y, -z+1 HTAB C32 Cl7B_$5 HTAB C32 Cl8B_$5 HTAB C34 Cl7B_$5 HTAB C34 Cl8B_$5 HTAB C37 Cl8 HTAB C4 O11 HTAB N32 O12_$1 EQIV $2 -x+1, -y, -z+1 HTAB C5 O22_$2 REM Highest difference peak 0.388, deepest hole -0.461, 1-sigma level 0.054 Q1 1 0.1324 0.2484 0.1994 11.00000 0.05 0.39 Q2 1 0.3029 0.0154 0.1812 11.00000 0.05 0.34 Q3 1 -0.1304 0.2379 0.0842 11.00000 0.05 0.33 Q4 1 0.1753 0.0318 0.0023 11.00000 0.05 0.29 Q5 1 0.1203 0.0390 0.6326 11.00000 0.05 0.28 Q6 1 0.0181 0.0961 0.2809 11.00000 0.05 0.26 Q7 1 0.2949 -0.0320 -0.0927 11.00000 0.05 0.25 Q8 1 0.0754 0.1199 0.3487 11.00000 0.05 0.25 Q9 1 0.3623 0.0869 0.3012 11.00000 0.05 0.25 Q10 1 0.1332 0.0158 0.1807 11.00000 0.05 0.24 ; _shelx_res_checksum 21631 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 0.21669(2) 0.01201(2) 0.17792(2) 0.02429(7) Uani 1 1 d . . . . . O11 O 0.11282(12) 0.06894(6) 0.09074(8) 0.0307(3) Uani 1 1 d . . . . . O12 O 0.06539(14) 0.08982(7) -0.04649(8) 0.0375(3) Uani 1 1 d . . . . . O21 O 0.40336(12) 0.03299(7) 0.22670(8) 0.0326(3) Uani 1 1 d . . . . . O22 O 0.53003(13) 0.09803(8) 0.31598(11) 0.0466(4) Uani 1 1 d . . . . . C11 C 0.23010(16) 0.00943(8) -0.00359(10) 0.0245(3) Uani 1 1 d . . . . . C12 C 0.26726(18) 0.00315(9) -0.08450(11) 0.0294(3) Uani 1 1 d . . . . . H12 H 0.224463 0.027319 -0.129426 0.035 Uiso 1 1 calc R . . . . C13 C 0.36757(18) -0.03917(9) -0.09601(11) 0.0308(4) Uani 1 1 d . . . . . H13 H 0.396708 -0.042609 -0.148397 0.037 Uiso 1 1 calc R . . . . C14 C 0.42626(17) -0.07747(8) -0.02770(11) 0.0272(3) Uani 1 1 d . . . . . C15 C 0.53051(18) -0.12259(9) -0.03448(12) 0.0327(4) Uani 1 1 d . . . . . H15 H 0.562530 -0.127709 -0.085771 0.039 Uiso 1 1 calc R . . . . C16 C 0.58390(19) -0.15836(9) 0.03340(14) 0.0362(4) Uani 1 1 d . . . . . H16 H 0.652306 -0.187697 0.028161 0.043 Uiso 1 1 calc R . . . . C17 C 0.53656(19) -0.15147(9) 0.11192(13) 0.0357(4) Uani 1 1 d . . . . . H17 H 0.572741 -0.176961 0.157537 0.043 Uiso 1 1 calc R . . . . C18 C 0.43771(18) -0.10747(9) 0.12128(12) 0.0320(4) Uani 1 1 d . . . . . H18 H 0.408160 -0.102566 0.173366 0.038 Uiso 1 1 calc R . . . . C19 C 0.38078(16) -0.06959(8) 0.05180(11) 0.0251(3) Uani 1 1 d . . . . . C21 C 0.29954(15) 0.10194(8) 0.31821(10) 0.0254(3) Uani 1 1 d . . . . . C22 C 0.30932(18) 0.14397(10) 0.38843(12) 0.0330(4) Uani 1 1 d . . . . . H22 H 0.391233 0.157641 0.414871 0.040 Uiso 1 1 calc R . . . . C23 C 0.19673(18) 0.16440(10) 0.41715(12) 0.0336(4) Uani 1 1 d . . . . . H23 H 0.201283 0.191555 0.464301 0.040 Uiso 1 1 calc R . . . . C24 C 0.07310(17) 0.14433(8) 0.37532(10) 0.0264(3) Uani 1 1 d . . . . . C25 C -0.04804(18) 0.16355(9) 0.40151(12) 0.0325(4) Uani 1 1 d . . . . . H25 H -0.048249 0.189636 0.449318 0.039 Uiso 1 1 calc R . . . . C26 C -0.16426(18) 0.14403(10) 0.35704(13) 0.0359(4) Uani 1 1 d . . . . . H26 H -0.243467 0.156574 0.374831 0.043 Uiso 1 1 calc R . . . . C27 C -0.16504(18) 0.10510(11) 0.28451(13) 0.0380(4) Uani 1 1 d . . . . . H27 H -0.245163 0.093254 0.253819 0.046 Uiso 1 1 calc R . . . . C28 C -0.05032(17) 0.08419(10) 0.25801(12) 0.0329(4) Uani 1 1 d . . . . . H28 H -0.052578 0.057849 0.210253 0.039 Uiso 1 1 calc R . . . . C29 C 0.07147(16) 0.10291(8) 0.30370(10) 0.0246(3) Uani 1 1 d . . . . . C31 C 0.02874(19) -0.20375(9) 0.19217(12) 0.0333(4) Uani 1 1 d . . . . . H31A H 0.060189 -0.248422 0.185208 0.040 Uiso 1 1 calc R . . . . H31B H 0.042930 -0.178281 0.142858 0.040 Uiso 1 1 calc R . . . . C32 C -0.1166(2) -0.20522(12) 0.20045(13) 0.0416(5) Uani 1 1 d . . . . . H32A H -0.164581 -0.226378 0.151334 0.050 Uiso 1 1 calc R . . . . H32B H -0.149249 -0.160352 0.203453 0.050 Uiso 1 1 calc R . . . . C33 C -0.1394(2) -0.24318(13) 0.27980(14) 0.0485(5) Uani 1 1 d . . . . . H33A H -0.231608 -0.240108 0.287416 0.058 Uiso 1 1 calc R . . . . H33B H -0.118509 -0.289520 0.273031 0.058 Uiso 1 1 calc R . . . . C34 C -0.0550(2) -0.21594(11) 0.35738(12) 0.0384(4) Uani 1 1 d . . . . . H34A H -0.085801 -0.172104 0.369778 0.046 Uiso 1 1 calc R . . . . H34B H -0.063415 -0.244190 0.405308 0.046 Uiso 1 1 calc R . . . . C35 C 0.0887(2) -0.21228(10) 0.34367(12) 0.0372(4) Uani 1 1 d . . . . . H35A H 0.139876 -0.191666 0.392068 0.045 Uiso 1 1 calc R . . . . H35B H 0.122722 -0.256600 0.337833 0.045 Uiso 1 1 calc R . . . . C36 C 0.14539(16) -0.11078(9) 0.26924(11) 0.0276(3) Uani 1 1 d . . . . . C37 C 0.2211(2) -0.08546(11) 0.34949(13) 0.0441(5) Uani 1 1 d . . . . . H37A H 0.265001 -0.045060 0.338428 0.066 Uiso 1 1 calc GR . . . . H37B H 0.285166 -0.117809 0.371566 0.066 Uiso 1 1 calc GR . . . . H37C H 0.161517 -0.077300 0.389827 0.066 Uiso 1 1 calc GR . . . . C110 C 0.12645(17) 0.06007(8) 0.01334(11) 0.0276(3) Uani 1 1 d . . . . . C210 C 0.42251(16) 0.07608(9) 0.28480(12) 0.0303(4) Uani 1 1 d . . . . . N1 N 0.28448(14) -0.02449(7) 0.06223(9) 0.0241(3) Uani 1 1 d . . . . . N2 N 0.18597(13) 0.08172(7) 0.27720(9) 0.0233(3) Uani 1 1 d . . . . . N31 N 0.10202(15) -0.17382(8) 0.26774(10) 0.0322(3) Uani 1 1 d . . . . . N32 N 0.12757(14) -0.07103(7) 0.20470(9) 0.0274(3) Uani 1 1 d . . . . . C4 C 0.0158(2) 0.21261(10) 0.09180(13) 0.0368(4) Uani 1 1 d . . . . . H4 H 0.059308 0.169334 0.094669 0.044 Uiso 1 1 calc R . . . . Cl41 Cl -0.15311(5) 0.20074(3) 0.05998(4) 0.05272(14) Uani 1 1 d . . . . . Cl42 Cl 0.04525(7) 0.24982(3) 0.19201(3) 0.05343(15) Uani 1 1 d . . . . . Cl43 Cl 0.08526(5) 0.26229(3) 0.01782(3) 0.04315(12) Uani 1 1 d . . . . . C5 C 0.3080(3) 0.02627(15) 0.6151(2) 0.0717(9) Uani 1 1 d . . . . . Cl5 Cl 0.156(2) 0.0246(12) 0.5622(11) 0.063(4) Uani 0.245(3) 1 d . U P A 1 Cl5A Cl 0.4387(6) 0.0392(5) 0.5462(5) 0.094(2) Uani 0.245(3) 1 d . U P A 1 Cl5B Cl 0.3250(7) 0.0749(3) 0.6945(4) 0.0702(16) Uani 0.245(3) 1 d . U P A 1 Cl6 Cl 0.1619(15) 0.0296(10) 0.5460(13) 0.044(2) Uani 0.275(3) 1 d . U P A 2 Cl6A Cl 0.4289(5) 0.0067(3) 0.5271(3) 0.0725(12) Uani 0.275(3) 1 d . U P A 2 Cl6B Cl 0.3660(5) 0.0980(3) 0.6524(5) 0.0734(18) Uani 0.275(3) 1 d . U P A 2 Cl7 Cl 0.161(3) 0.0189(12) 0.5379(18) 0.058(4) Uani 0.245(3) 1 d . U P A 3 Cl7A Cl 0.4044(7) 0.0939(3) 0.6202(5) 0.071(2) Uani 0.245(3) 1 d . U P A 3 Cl7B Cl 0.2550(11) 0.0644(2) 0.7110(2) 0.0718(17) Uani 0.245(3) 1 d . U P A 3 Cl8 Cl 0.2228(8) 0.0050(3) 0.5311(4) 0.0760(17) Uani 0.235(3) 1 d . U P A 4 Cl8A Cl 0.4201(7) 0.0832(6) 0.5833(6) 0.086(2) Uani 0.235(3) 1 d . U P A 4 Cl8B Cl 0.1749(7) 0.0552(2) 0.6933(3) 0.0754(15) Uani 0.235(3) 1 d . U P A 4 H32 H 0.078(2) -0.0847(11) 0.1617(15) 0.031(5) Uiso 1 1 d . . . . . H5 H 0.337(3) -0.0113(14) 0.6417(19) 0.055(8) 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 0.02392(12) 0.02545(12) 0.02367(12) 0.00094(8) 0.00383(8) 0.00141(8) O11 0.0347(6) 0.0310(6) 0.0264(6) 0.0020(5) 0.0038(5) 0.0084(5) O12 0.0406(7) 0.0410(7) 0.0288(6) 0.0052(5) -0.0036(5) 0.0107(6) O21 0.0215(6) 0.0412(7) 0.0362(6) -0.0029(5) 0.0077(5) 0.0018(5) O22 0.0190(6) 0.0521(9) 0.0682(10) -0.0104(8) 0.0032(6) -0.0066(6) C11 0.0256(8) 0.0221(7) 0.0249(8) -0.0020(6) 0.0006(6) -0.0038(6) C12 0.0314(9) 0.0331(9) 0.0226(8) -0.0010(6) -0.0007(6) -0.0046(7) C13 0.0331(9) 0.0356(9) 0.0236(8) -0.0082(7) 0.0041(7) -0.0079(7) C14 0.0269(8) 0.0259(8) 0.0292(8) -0.0071(6) 0.0057(6) -0.0070(6) C15 0.0314(9) 0.0302(9) 0.0384(9) -0.0119(7) 0.0115(7) -0.0043(7) C16 0.0314(9) 0.0277(9) 0.0509(11) -0.0070(8) 0.0113(8) 0.0043(7) C17 0.0349(9) 0.0299(9) 0.0427(10) 0.0047(8) 0.0064(8) 0.0049(7) C18 0.0326(9) 0.0313(9) 0.0330(9) 0.0025(7) 0.0077(7) 0.0037(7) C19 0.0236(7) 0.0229(7) 0.0292(8) -0.0031(6) 0.0049(6) -0.0031(6) C21 0.0197(7) 0.0273(8) 0.0287(8) 0.0010(6) 0.0017(6) -0.0037(6) C22 0.0259(8) 0.0396(10) 0.0322(9) -0.0051(7) -0.0006(7) -0.0109(7) C23 0.0327(9) 0.0369(9) 0.0306(9) -0.0094(7) 0.0018(7) -0.0060(7) C24 0.0275(8) 0.0267(8) 0.0248(7) 0.0001(6) 0.0027(6) -0.0003(6) C25 0.0336(9) 0.0329(9) 0.0317(9) -0.0023(7) 0.0072(7) 0.0049(7) C26 0.0257(8) 0.0419(10) 0.0411(10) 0.0006(8) 0.0082(7) 0.0085(7) C27 0.0205(8) 0.0539(12) 0.0384(10) -0.0043(9) -0.0006(7) 0.0009(8) C28 0.0223(8) 0.0448(10) 0.0308(8) -0.0078(7) 0.0008(7) -0.0011(7) C29 0.0211(7) 0.0279(8) 0.0243(7) -0.0003(6) 0.0020(6) -0.0006(6) C31 0.0396(10) 0.0291(9) 0.0312(9) -0.0022(7) 0.0043(7) -0.0034(7) C32 0.0363(10) 0.0548(12) 0.0311(9) 0.0011(8) -0.0049(8) -0.0091(9) C33 0.0375(11) 0.0687(15) 0.0386(11) 0.0055(10) 0.0018(8) -0.0193(10) C34 0.0415(10) 0.0442(11) 0.0291(9) 0.0059(8) 0.0027(8) -0.0035(8) C35 0.0390(10) 0.0357(10) 0.0340(9) 0.0126(8) -0.0057(7) -0.0059(8) C36 0.0230(8) 0.0314(9) 0.0279(8) 0.0025(6) 0.0018(6) -0.0022(6) C37 0.0527(12) 0.0416(11) 0.0331(10) 0.0083(8) -0.0122(9) -0.0158(9) C110 0.0270(8) 0.0260(8) 0.0287(8) 0.0002(6) -0.0007(6) -0.0007(6) C210 0.0198(8) 0.0335(9) 0.0376(9) 0.0041(7) 0.0041(7) -0.0017(6) N1 0.0255(7) 0.0240(7) 0.0232(6) -0.0003(5) 0.0052(5) -0.0006(5) N2 0.0194(6) 0.0256(7) 0.0248(6) -0.0006(5) 0.0019(5) -0.0011(5) N31 0.0331(8) 0.0319(8) 0.0296(7) 0.0066(6) -0.0027(6) -0.0062(6) N32 0.0285(7) 0.0291(7) 0.0242(7) 0.0010(6) 0.0018(6) -0.0035(6) C4 0.0383(10) 0.0336(9) 0.0372(10) -0.0015(8) -0.0003(8) 0.0099(8) Cl41 0.0339(2) 0.0599(3) 0.0632(3) 0.0059(3) 0.0024(2) 0.0062(2) Cl42 0.0800(4) 0.0478(3) 0.0319(2) -0.0013(2) 0.0049(2) 0.0018(3) Cl43 0.0403(2) 0.0553(3) 0.0330(2) -0.0001(2) 0.00170(18) 0.0012(2) C5 0.0696(18) 0.0528(15) 0.082(2) 0.0207(15) -0.0296(16) -0.0050(13) Cl5 0.071(4) 0.047(4) 0.062(7) 0.015(5) -0.020(5) 0.000(3) Cl5A 0.070(2) 0.126(6) 0.084(5) 0.041(4) 0.000(3) -0.007(4) Cl5B 0.084(3) 0.060(3) 0.058(3) -0.017(2) -0.022(3) 0.016(2) Cl6 0.043(3) 0.047(4) 0.036(6) 0.007(4) -0.017(4) -0.010(2) Cl6A 0.070(2) 0.087(3) 0.0604(19) 0.008(2) 0.0077(15) 0.020(2) Cl6B 0.069(3) 0.064(2) 0.079(4) -0.024(3) -0.021(3) 0.014(2) Cl7 0.069(5) 0.054(6) 0.043(5) -0.004(3) -0.018(4) -0.012(5) Cl7A 0.074(4) 0.058(3) 0.075(5) 0.009(3) -0.009(3) -0.026(3) Cl7B 0.129(5) 0.0497(19) 0.0400(15) -0.0004(12) 0.022(3) 0.022(3) Cl8 0.113(5) 0.072(3) 0.0426(17) -0.0042(19) 0.007(3) -0.035(3) Cl8A 0.062(2) 0.108(5) 0.084(5) 0.029(4) -0.005(3) -0.022(3) Cl8B 0.109(4) 0.053(2) 0.075(3) 0.0177(19) 0.052(3) 0.036(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' Cl Cl 0.3639 0.7018 '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' 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 O11 Zn1 O21 122.61(6) . . ? O11 Zn1 N1 78.59(5) . . ? O11 Zn1 N2 91.30(5) . . ? O21 Zn1 N1 90.46(5) . . ? O21 Zn1 N2 78.58(5) . . ? N2 Zn1 N1 158.09(5) . . ? N32 Zn1 O11 114.83(6) . . ? N32 Zn1 O21 122.33(6) . . ? N32 Zn1 N1 96.00(6) . . ? N32 Zn1 N2 105.90(6) . . ? C110 O11 Zn1 118.64(11) . . ? C210 O21 Zn1 118.37(11) . . ? C12 C11 C110 120.35(15) . . ? N1 C11 C12 123.65(16) . . ? N1 C11 C110 115.93(15) . . ? C11 C12 H12 120.6 . . ? C13 C12 C11 118.78(16) . . ? C13 C12 H12 120.6 . . ? C12 C13 H13 120.3 . . ? C12 C13 C14 119.31(16) . . ? C14 C13 H13 120.3 . . ? C13 C14 C15 122.78(16) . . ? C13 C14 C19 118.54(16) . . ? C15 C14 C19 118.67(16) . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.49(17) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 119.6 . . ? C15 C16 C17 120.70(17) . . ? C17 C16 H16 119.6 . . ? C16 C17 H17 119.8 . . ? C18 C17 C16 120.45(18) . . ? C18 C17 H17 119.8 . . ? C17 C18 H18 120.0 . . ? C17 C18 C19 119.96(17) . . ? C19 C18 H18 120.0 . . ? C18 C19 C14 119.70(16) . . ? N1 C19 C14 120.72(15) . . ? N1 C19 C18 119.56(15) . . ? C22 C21 C210 121.00(15) . . ? N2 C21 C22 123.38(15) . . ? N2 C21 C210 115.62(15) . . ? C21 C22 H22 120.6 . . ? C23 C22 C21 118.78(16) . . ? C23 C22 H22 120.6 . . ? C22 C23 H23 120.0 . . ? C22 C23 C24 119.94(16) . . ? C24 C23 H23 120.0 . . ? C23 C24 C25 123.13(16) . . ? C23 C24 C29 117.85(15) . . ? C25 C24 C29 119.03(16) . . ? C24 C25 H25 119.8 . . ? C26 C25 C24 120.30(17) . . ? C26 C25 H25 119.8 . . ? C25 C26 H26 119.8 . . ? C25 C26 C27 120.30(17) . . ? C27 C26 H26 119.8 . . ? C26 C27 H27 119.3 . . ? C28 C27 C26 121.32(17) . . ? C28 C27 H27 119.3 . . ? C27 C28 H28 120.2 . . ? C27 C28 C29 119.50(17) . . ? C29 C28 H28 120.2 . . ? C28 C29 C24 119.48(15) . . ? N2 C29 C24 121.16(15) . . ? N2 C29 C28 119.35(15) . . ? H31A C31 H31B 108.2 . . ? C32 C31 H31A 109.7 . . ? C32 C31 H31B 109.7 . . ? N31 C31 H31A 109.7 . . ? N31 C31 H31B 109.7 . . ? N31 C31 C32 109.70(16) . . ? C31 C32 H32A 109.6 . . ? C31 C32 H32B 109.6 . . ? C31 C32 C33 110.10(17) . . ? H32A C32 H32B 108.2 . . ? C33 C32 H32A 109.6 . . ? C33 C32 H32B 109.6 . . ? C32 C33 H33A 109.3 . . ? C32 C33 H33B 109.3 . . ? H33A C33 H33B 108.0 . . ? C34 C33 C32 111.40(17) . . ? C34 C33 H33A 109.3 . . ? C34 C33 H33B 109.3 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 108.1 . . ? C35 C34 C33 110.88(17) . . ? C35 C34 H34A 109.5 . . ? C35 C34 H34B 109.5 . . ? C34 C35 H35A 109.6 . . ? C34 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? N31 C35 C34 110.15(15) . . ? N31 C35 H35A 109.6 . . ? N31 C35 H35B 109.6 . . ? N31 C36 C37 117.97(16) . . ? N32 C36 C37 118.13(16) . . ? N32 C36 N31 123.88(16) . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37B 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O11 C110 C11 115.78(15) . . ? O12 C110 O11 125.28(16) . . ? O12 C110 C11 118.92(16) . . ? O21 C210 C21 115.97(14) . . ? O22 C210 O21 125.98(17) . . ? O22 C210 C21 118.05(17) . . ? C11 N1 Zn1 110.73(11) . . ? C11 N1 C19 118.90(14) . . ? C19 N1 Zn1 129.91(11) . . ? C21 N2 Zn1 111.10(11) . . ? C21 N2 C29 118.86(14) . . ? C29 N2 Zn1 129.94(11) . . ? C35 N31 C31 111.87(15) . . ? C36 N31 C31 122.37(15) . . ? C36 N31 C35 123.59(16) . . ? Zn1 N32 H32 110.1(15) . . ? C36 N32 Zn1 132.32(12) . . ? C36 N32 H32 116.8(15) . . ? Cl41 C4 H4 108.4 . . ? Cl41 C4 Cl42 111.48(11) . . ? Cl41 C4 Cl43 110.55(11) . . ? Cl42 C4 H4 108.4 . . ? Cl42 C4 Cl43 109.39(11) . . ? Cl43 C4 H4 108.4 . . ? Cl5 C5 Cl5A 113.3(7) . . ? Cl5 C5 H5 116(2) . . ? Cl5A C5 H5 100.6(19) . . ? Cl5B C5 Cl5 114.3(9) . . ? Cl5B C5 Cl5A 112.0(4) . . ? Cl5B C5 H5 98.6(19) . . ? Cl6 C5 Cl6A 96.7(7) . . ? Cl6 C5 H5 122(2) . . ? Cl6A C5 H5 88.5(19) . . ? Cl6B C5 Cl6 115.7(7) . . ? Cl6B C5 Cl6A 101.5(3) . . ? Cl6B C5 H5 119.5(19) . . ? Cl7 C5 Cl7B 106.9(10) . . ? Cl7 C5 H5 116(2) . . ? Cl7A C5 Cl7 121.7(9) . . ? Cl7A C5 Cl7B 81.8(4) . . ? Cl7A C5 H5 120.8(19) . . ? Cl7B C5 H5 94.1(19) . . ? Cl8 C5 Cl8A 104.0(4) . . ? Cl8 C5 Cl8B 105.3(3) . . ? Cl8 C5 H5 106.5(19) . . ? Cl8A C5 Cl8B 120.3(5) . . ? Cl8A C5 H5 120.6(19) . . ? Cl8B C5 H5 98.8(19) . . ? Cl6A Cl6A C5 164.2(5) 3_656 . ? C5 Cl7A Cl7B 52.5(3) . . ? C5 Cl7B Cl7A 45.8(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 O11 2.0028(12) . ? Zn1 O21 2.0118(12) . ? Zn1 N1 2.1917(14) . ? Zn1 N2 2.1787(14) . ? Zn1 N32 1.9845(15) . ? O11 C110 1.279(2) . ? O12 C110 1.230(2) . ? O21 C210 1.271(2) . ? O22 C210 1.230(2) . ? C11 C12 1.404(2) . ? C11 C110 1.524(2) . ? C11 N1 1.318(2) . ? C12 H12 0.9300 . ? C12 C13 1.368(3) . ? C13 H13 0.9300 . ? C13 C14 1.408(3) . ? C14 C15 1.419(3) . ? C14 C19 1.422(2) . ? C15 H15 0.9300 . ? C15 C16 1.359(3) . ? C16 H16 0.9300 . ? C16 C17 1.414(3) . ? C17 H17 0.9300 . ? C17 C18 1.370(3) . ? C18 H18 0.9300 . ? C18 C19 1.412(2) . ? C19 N1 1.369(2) . ? C21 C22 1.403(2) . ? C21 C210 1.525(2) . ? C21 N2 1.322(2) . ? C22 H22 0.9300 . ? C22 C23 1.361(3) . ? C23 H23 0.9300 . ? C23 C24 1.411(2) . ? C24 C25 1.416(2) . ? C24 C29 1.419(2) . ? C25 H25 0.9300 . ? C25 C26 1.362(3) . ? C26 H26 0.9300 . ? C26 C27 1.402(3) . ? C27 H27 0.9300 . ? C27 C28 1.368(3) . ? C28 H28 0.9300 . ? C28 C29 1.411(2) . ? C29 N2 1.368(2) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 C32 1.512(3) . ? C31 N31 1.467(2) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C33 1.529(3) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 C34 1.520(3) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 C35 1.518(3) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C35 N31 1.465(2) . ? C36 C37 1.500(2) . ? C36 N31 1.348(2) . ? C36 N32 1.303(2) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? N32 H32 0.85(2) . ? C4 H4 0.9800 . ? C4 Cl41 1.753(2) . ? C4 Cl42 1.762(2) . ? C4 Cl43 1.773(2) . ? C5 Cl5 1.67(2) . ? C5 Cl5A 1.864(8) . ? C5 Cl5B 1.599(6) . ? C5 Cl6 1.739(16) . ? C5 Cl6A 2.036(6) . ? C5 Cl6B 1.648(6) . ? C5 Cl7 1.82(3) . ? C5 Cl7A 1.683(6) . ? C5 Cl7B 1.862(6) . ? C5 Cl8 1.563(7) . ? C5 Cl8A 1.749(8) . ? C5 Cl8B 2.055(6) . ? C5 H5 0.90(3) . ? Cl6A Cl6A 1.811(10) 3_656 ? Cl7A Cl7B 2.325(10) . ? 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 0.85(2) 2.20(2) 3.023(2) 163(2) 3 yes