#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:42:26 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258103 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240532.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_7240532 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 'C26 H24 N4 O4 Zn, C H2 Cl2' _chemical_formula_sum 'C27 H26 Cl2 N4 O4 Zn' _chemical_formula_weight 606.79 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 114.123(3) _cell_angle_beta 99.089(2) _cell_angle_gamma 93.237(2) _cell_formula_units_Z 2 _cell_length_a 7.9088(2) _cell_length_b 12.5987(4) _cell_length_c 14.7809(5) _cell_measurement_reflns_used 9081 _cell_measurement_temperature 125.00(10) _cell_measurement_theta_max 29.7610 _cell_measurement_theta_min 3.0530 _cell_volume 1315.26(8) _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 125.00(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 1.000 _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 -86.00 -56.00 1.00 12.50 -- -14.36 147.00 18.79 30 2 \w -14.00 92.00 1.00 12.50 -- 14.52 77.00 90.00 106 3 \w 43.00 103.00 1.00 12.50 -- 14.52-178.00 90.00 60 4 \w -53.00 44.00 1.00 12.50 -- 14.52 -57.00-180.00 97 5 \w 35.00 84.00 1.00 12.50 -- 14.52 178.00-180.00 49 6 \w -18.00 56.00 1.00 12.50 -- 14.52 -99.00 -60.00 74 7 \w -12.00 91.00 1.00 12.50 -- 14.52 37.00-120.00 103 8 \w -15.00 85.00 1.00 12.50 -- 14.52 57.00 -30.00 100 ; _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 0.0310514000 _diffrn_orient_matrix_UB_12 0.0608188000 _diffrn_orient_matrix_UB_13 0.0257217000 _diffrn_orient_matrix_UB_21 -0.0447581000 _diffrn_orient_matrix_UB_22 0.0089853000 _diffrn_orient_matrix_UB_23 -0.0412771000 _diffrn_orient_matrix_UB_31 -0.0737112000 _diffrn_orient_matrix_UB_32 0.0097695000 _diffrn_orient_matrix_UB_33 0.0226452000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_unetI/netI 0.0330 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 20933 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_min 2.632 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.179 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89426 _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 1.532 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.985 _refine_diff_density_min -0.666 _refine_diff_density_rms 0.073 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 376 _refine_ls_number_reflns 6040 _refine_ls_number_restraints 42 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0382 _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^)+(0.0518P)^2^+1.2271P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0984 _refine_ls_wR_factor_ref 0.1030 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5319 _reflns_number_total 6040 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03192e3.cif _cod_data_source_block 10c _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 7240532 _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 0.943 _shelx_estimated_absorpt_t_min 0.719 _shelx_res_file ; TITL mob536_a.res in P-1 mob536.res created by SHELXL-2018/3 at 11:26:32 on 16-Dec-2019 CELL 0.71073 7.9088 12.5987 14.7809 114.123 99.089 93.237 ZERR 2 0.0002 0.0004 0.0005 0.003 0.002 0.002 LATT 1 SFAC C H Cl N O Zn UNIT 54 52 4 8 8 2 EQIV $1 1+X,+Y,+Z SADI 0.01 C1 Cl1 C1A Cl1A SADI 0.01 C1 Cl2 C1A Cl2A SADI 0.01 Cl1 Cl2 Cl1A Cl2A DELU 0.005 0.005 Cl1 > Cl2A SIMU 0.01 0.02 2 Cl1 > Cl2A L.S. 10 PLAN 10 SIZE 0.3 0.2 0.05 MPLA N1 C11 C12 C13 C14 C15 C16 C17 C18 C19 MPLA N2 C21 C22 C23 C24 C25 C26 C27 C28 C29 HTAB N32 O22_$1 MORE -1 BOND $H htab CONF LIST 6 fmap 2 acta MERG 2 SHEL 30 0.7696 REM REM REM WGHT 0.051800 1.227100 FVAR 4.44124 0.29046 ZN1 6 0.610884 0.344001 0.685964 11.00000 0.01424 0.01554 = 0.01859 0.00352 0.00575 0.00277 O11 5 0.729073 0.302125 0.795363 11.00000 0.02506 0.02188 = 0.01932 0.00392 0.00637 0.00804 O12 5 0.843319 0.158684 0.825193 11.00000 0.03778 0.02963 = 0.02342 0.00921 -0.00239 0.00852 O21 5 0.358191 0.305414 0.619389 11.00000 0.01516 0.01917 = 0.02293 0.00269 0.00420 0.00247 O22 5 0.090505 0.321781 0.649501 11.00000 0.01503 0.02122 = 0.03775 0.00753 0.00541 0.00260 N1 4 0.675651 0.173109 0.596611 11.00000 0.01258 0.01576 = 0.02003 0.00463 0.00583 0.00124 N2 4 0.493427 0.471189 0.800278 11.00000 0.01764 0.01735 = 0.01960 0.00642 0.00709 0.00403 N31 4 0.877719 0.606345 0.630843 11.00000 0.01592 0.02078 = 0.03029 0.01290 0.00703 0.00561 N32 4 0.768108 0.441815 0.648303 11.00000 0.01405 0.01906 = 0.02596 0.00808 0.00870 0.00544 H32 2 0.861076 0.421033 0.646673 11.00000 0.02272 C11 1 0.762384 0.130187 0.654690 11.00000 0.01297 0.01655 = 0.02115 0.00502 0.00460 -0.00008 C12 1 0.833748 0.024255 0.616635 11.00000 0.01837 0.01620 = 0.02747 0.00864 0.00428 0.00166 AFIX 43 H12 2 0.892831 -0.003210 0.660525 11.00000 -1.20000 AFIX 0 C13 1 0.814938 -0.037298 0.514675 11.00000 0.02017 0.01277 = 0.03092 0.00633 0.00960 0.00244 AFIX 43 H13 2 0.862509 -0.106794 0.488211 11.00000 -1.20000 AFIX 0 C14 1 0.722720 0.005247 0.449585 11.00000 0.01696 0.01381 = 0.02385 0.00382 0.00853 -0.00005 C15 1 0.697728 -0.052686 0.342598 11.00000 0.02581 0.01543 = 0.02451 0.00258 0.01022 0.00042 AFIX 43 H15 2 0.744806 -0.121681 0.312506 11.00000 -1.20000 AFIX 0 C16 1 0.605306 -0.008042 0.283593 11.00000 0.02856 0.02002 = 0.01983 0.00213 0.00721 -0.00217 AFIX 43 H16 2 0.591019 -0.046412 0.213599 11.00000 -1.20000 AFIX 0 C17 1 0.531144 0.095679 0.327546 11.00000 0.01974 0.02437 = 0.02295 0.00861 0.00396 0.00072 AFIX 43 H17 2 0.466005 0.124150 0.286362 11.00000 -1.20000 AFIX 0 C18 1 0.554446 0.154748 0.430506 11.00000 0.01764 0.01845 = 0.02280 0.00543 0.00633 0.00262 AFIX 43 H18 2 0.505862 0.223454 0.458977 11.00000 -1.20000 AFIX 0 C19 1 0.651838 0.111752 0.493481 11.00000 0.01292 0.01416 = 0.01980 0.00337 0.00649 -0.00029 C21 1 0.324879 0.440639 0.781739 11.00000 0.01950 0.01583 = 0.02256 0.00900 0.00772 0.00547 C22 1 0.220947 0.490661 0.853542 11.00000 0.01813 0.02488 = 0.02827 0.01172 0.01025 0.00719 AFIX 43 H22 2 0.102845 0.465520 0.838030 11.00000 -1.20000 AFIX 0 C23 1 0.296811 0.576873 0.946491 11.00000 0.02602 0.02474 = 0.02570 0.00978 0.01525 0.01154 AFIX 43 H23 2 0.230747 0.610217 0.995236 11.00000 -1.20000 AFIX 0 C24 1 0.476089 0.614953 0.967993 11.00000 0.02705 0.01971 = 0.02051 0.00780 0.01014 0.00844 C25 1 0.563842 0.705599 1.061462 11.00000 0.03324 0.02306 = 0.02100 0.00484 0.01142 0.01071 AFIX 43 H25 2 0.503012 0.742752 1.112171 11.00000 -1.20000 AFIX 0 C26 1 0.737331 0.738473 1.077214 11.00000 0.03681 0.02297 = 0.01870 0.00148 0.00446 0.00509 AFIX 43 H26 2 0.793656 0.798495 1.138468 11.00000 -1.20000 AFIX 0 C27 1 0.832022 0.682329 1.001531 11.00000 0.02468 0.02473 = 0.02403 0.00540 0.00429 0.00079 AFIX 43 H27 2 0.950090 0.705816 1.013395 11.00000 -1.20000 AFIX 0 C28 1 0.752103 0.593760 0.910926 11.00000 0.02086 0.02432 = 0.02194 0.00419 0.00740 0.00363 AFIX 43 H28 2 0.815838 0.556639 0.861791 11.00000 -1.20000 AFIX 0 C29 1 0.572330 0.558809 0.892190 11.00000 0.02150 0.01620 = 0.01979 0.00497 0.00641 0.00392 C31 1 1.057379 0.582868 0.642844 11.00000 0.01659 0.02568 = 0.03926 0.01696 0.00775 0.00564 AFIX 23 H31A 2 1.069482 0.506904 0.591478 11.00000 -1.20000 H31B 2 1.097465 0.584814 0.709074 11.00000 -1.20000 AFIX 0 C32 1 1.156553 0.680762 0.630696 11.00000 0.02497 0.03779 = 0.09368 0.04077 0.02243 0.00883 AFIX 23 H32A 2 1.259222 0.714318 0.683668 11.00000 -1.20000 H32B 2 1.191913 0.650754 0.565824 11.00000 -1.20000 AFIX 0 C33 1 1.043799 0.769342 0.636966 11.00000 0.02226 0.04610 = 0.14348 0.06433 0.00604 0.00329 AFIX 23 H33A 2 1.055701 0.797522 0.585954 11.00000 -1.20000 H33B 2 1.075659 0.835342 0.702892 11.00000 -1.20000 AFIX 0 C34 1 0.862021 0.717535 0.620815 11.00000 0.02420 0.02755 = 0.04477 0.02279 0.01224 0.00907 AFIX 23 H34A 2 0.803368 0.769021 0.671326 11.00000 -1.20000 H34B 2 0.798924 0.703032 0.554135 11.00000 -1.20000 AFIX 0 C35 1 0.749297 0.538813 0.638609 11.00000 0.01598 0.02147 = 0.01837 0.00607 0.00513 0.00357 C36 1 0.574485 0.579852 0.637085 11.00000 0.01795 0.03393 = 0.04126 0.02130 0.01089 0.00995 AFIX 137 H36A 2 0.488587 0.517085 0.627184 11.00000 -1.50000 H36B 2 0.548480 0.603367 0.582850 11.00000 -1.50000 H36C 2 0.574749 0.645313 0.700247 11.00000 -1.50000 AFIX 0 C110 1 0.781744 0.202195 0.768650 11.00000 0.01573 0.02030 = 0.02095 0.00376 0.00217 0.00097 C210 1 0.248704 0.347904 0.675362 11.00000 0.01784 0.01270 = 0.02556 0.00664 0.00581 0.00313 PART 1 C1 1 0.830328 1.033020 0.970193 21.00000 0.16710 0.05594 = 0.08066 0.04022 -0.03188 0.00218 AFIX 23 H1A 2 0.949549 1.041357 0.963013 21.00000 -1.20000 H1B 2 0.769450 1.076744 0.937602 21.00000 -1.20000 AFIX 0 CL1 3 0.750919 0.889484 0.897784 21.00000 0.22007 0.10973 = 0.07745 0.05294 -0.08205 -0.01736 CL2 3 0.831760 1.101023 1.085387 21.00000 0.28185 0.21861 = 0.05278 0.01394 -0.01215 -0.04109 PART 0 PART 2 C1A 1 0.708823 1.056140 0.964479 -21.00000 0.22898 0.12314 = 0.10626 0.09194 -0.02718 -0.03704 AFIX 23 H1AA 2 0.788912 1.080674 0.931126 -21.00000 -1.20000 H1AB 2 0.595637 1.070426 0.939192 -21.00000 -1.20000 AFIX 0 CL1A 3 0.700871 0.905267 0.920166 -21.00000 0.29218 0.10762 = 0.10985 0.07522 0.00216 -0.01673 CL2A 3 0.757740 1.142319 1.078236 -21.00000 0.29648 0.10423 = 0.13432 0.06756 0.01176 0.03106 HKLF 4 REM mob536_a.res in P-1 REM wR2 = 0.1030, GooF = S = 1.032, Restrained GooF = 1.049 for all data REM R1 = 0.0382 for 5319 Fo > 4sig(Fo) and 0.0451 for all 6040 data REM 376 parameters refined using 42 restraints END WGHT 0.0518 1.2271 REM Instructions for potential hydrogen bonds HTAB N32 O22_$1 HTAB C18 O21 EQIV $2 -x+2, -y+2, -z+2 HTAB C33 Cl2_$2 EQIV $3 -x+1, -y+1, -z+1 HTAB C34 O21_$3 HTAB C1 Cl1_$2 HTAB C1 Cl2_$2 EQIV $4 x, y+1, z HTAB C1 O12_$4 HTAB C1A O12_$4 REM Highest difference peak 0.985, deepest hole -0.666, 1-sigma level 0.073 Q1 1 0.6391 0.2827 0.7191 11.00000 0.05 0.99 Q2 1 0.7014 1.1201 1.0204 11.00000 0.05 0.75 Q3 1 0.5804 0.3988 0.6418 11.00000 0.05 0.57 Q4 1 1.0788 0.8373 0.6309 11.00000 0.05 0.51 Q5 1 1.1625 0.7191 0.6971 11.00000 0.05 0.47 Q6 1 1.0292 0.7312 0.5801 11.00000 0.05 0.40 Q7 1 0.6738 1.1794 1.1208 11.00000 0.05 0.38 Q8 1 0.8637 0.6616 0.6326 11.00000 0.05 0.38 Q9 1 0.7213 -0.0196 0.4023 11.00000 0.05 0.34 Q10 1 0.7657 0.1597 0.7105 11.00000 0.05 0.34 ; _shelx_res_checksum 13337 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Zn1 Zn 0.61088(3) 0.34400(2) 0.68596(2) 0.01704(9) Uani 1 1 d . . . . . O11 O 0.7291(2) 0.30213(14) 0.79536(12) 0.0233(3) Uani 1 1 d . . . . . O12 O 0.8433(2) 0.15868(15) 0.82519(13) 0.0318(4) Uani 1 1 d . . . . . O21 O 0.35819(18) 0.30541(13) 0.61939(12) 0.0211(3) Uani 1 1 d . . . . . O22 O 0.09051(19) 0.32178(14) 0.64950(14) 0.0263(4) Uani 1 1 d . . . . . N1 N 0.6757(2) 0.17311(15) 0.59661(13) 0.0168(3) Uani 1 1 d . . . . . N2 N 0.4934(2) 0.47119(15) 0.80028(14) 0.0182(4) Uani 1 1 d . . . . . N31 N 0.8777(2) 0.60634(16) 0.63084(15) 0.0212(4) Uani 1 1 d . . . . . N32 N 0.7681(2) 0.44181(16) 0.64830(14) 0.0195(4) Uani 1 1 d . . . . . H32 H 0.861(4) 0.421(2) 0.647(2) 0.023(7) Uiso 1 1 d . . . . . C11 C 0.7624(3) 0.13019(18) 0.65469(16) 0.0178(4) Uani 1 1 d . . . . . C12 C 0.8337(3) 0.02425(18) 0.61663(18) 0.0209(4) Uani 1 1 d . . . . . H12 H 0.892831 -0.003210 0.660525 0.025 Uiso 1 1 calc R . . . . C13 C 0.8149(3) -0.03730(18) 0.51467(18) 0.0217(4) Uani 1 1 d . . . . . H13 H 0.862509 -0.106794 0.488211 0.026 Uiso 1 1 calc R . . . . C14 C 0.7227(3) 0.00525(18) 0.44959(17) 0.0192(4) Uani 1 1 d . . . . . C15 C 0.6977(3) -0.05269(19) 0.34260(17) 0.0234(5) Uani 1 1 d . . . . . H15 H 0.744806 -0.121681 0.312506 0.028 Uiso 1 1 calc R . . . . C16 C 0.6053(3) -0.0080(2) 0.28359(18) 0.0249(5) Uani 1 1 d . . . . . H16 H 0.591019 -0.046412 0.213599 0.030 Uiso 1 1 calc R . . . . C17 C 0.5311(3) 0.0957(2) 0.32755(18) 0.0230(4) Uani 1 1 d . . . . . H17 H 0.466005 0.124150 0.286362 0.028 Uiso 1 1 calc R . . . . C18 C 0.5544(3) 0.15475(19) 0.43051(17) 0.0205(4) Uani 1 1 d . . . . . H18 H 0.505862 0.223454 0.458977 0.025 Uiso 1 1 calc R . . . . C19 C 0.6518(2) 0.11175(17) 0.49348(16) 0.0166(4) Uani 1 1 d . . . . . C21 C 0.3249(3) 0.44064(18) 0.78174(17) 0.0184(4) Uani 1 1 d . . . . . C22 C 0.2209(3) 0.4907(2) 0.85354(18) 0.0227(5) Uani 1 1 d . . . . . H22 H 0.102845 0.465520 0.838030 0.027 Uiso 1 1 calc R . . . . C23 C 0.2968(3) 0.5769(2) 0.94649(18) 0.0242(5) Uani 1 1 d . . . . . H23 H 0.230747 0.610217 0.995236 0.029 Uiso 1 1 calc R . . . . C24 C 0.4761(3) 0.61495(19) 0.96799(17) 0.0218(4) Uani 1 1 d . . . . . C25 C 0.5638(3) 0.7056(2) 1.06146(18) 0.0263(5) Uani 1 1 d . . . . . H25 H 0.503012 0.742752 1.112171 0.032 Uiso 1 1 calc R . . . . C26 C 0.7373(3) 0.7385(2) 1.07721(18) 0.0287(5) Uani 1 1 d . . . . . H26 H 0.793656 0.798495 1.138468 0.034 Uiso 1 1 calc R . . . . C27 C 0.8320(3) 0.6823(2) 1.00153(18) 0.0263(5) Uani 1 1 d . . . . . H27 H 0.950090 0.705816 1.013395 0.032 Uiso 1 1 calc R . . . . C28 C 0.7521(3) 0.5938(2) 0.91093(17) 0.0239(5) Uani 1 1 d . . . . . H28 H 0.815838 0.556639 0.861791 0.029 Uiso 1 1 calc R . . . . C29 C 0.5723(3) 0.55881(18) 0.89219(17) 0.0197(4) Uani 1 1 d . . . . . C31 C 1.0574(3) 0.5829(2) 0.6428(2) 0.0257(5) Uani 1 1 d . . . . . H31A H 1.069482 0.506904 0.591478 0.031 Uiso 1 1 calc R . . . . H31B H 1.097465 0.584814 0.709074 0.031 Uiso 1 1 calc R . . . . C32 C 1.1566(3) 0.6808(3) 0.6307(3) 0.0463(8) Uani 1 1 d . . . . . H32A H 1.259222 0.714318 0.683668 0.056 Uiso 1 1 calc R . . . . H32B H 1.191913 0.650754 0.565824 0.056 Uiso 1 1 calc R . . . . C33 C 1.0438(4) 0.7693(3) 0.6370(4) 0.0638(12) Uani 1 1 d . . . . . H33A H 1.055701 0.797522 0.585954 0.077 Uiso 1 1 calc R . . . . H33B H 1.075659 0.835342 0.702892 0.077 Uiso 1 1 calc R . . . . C34 C 0.8620(3) 0.7175(2) 0.6208(2) 0.0288(5) Uani 1 1 d . . . . . H34A H 0.803368 0.769021 0.671326 0.035 Uiso 1 1 calc R . . . . H34B H 0.798924 0.703032 0.554135 0.035 Uiso 1 1 calc R . . . . C35 C 0.7493(3) 0.53881(19) 0.63861(16) 0.0192(4) Uani 1 1 d . . . . . C36 C 0.5745(3) 0.5799(2) 0.6371(2) 0.0284(5) Uani 1 1 d . . . . . H36A H 0.488587 0.517085 0.627184 0.043 Uiso 1 1 calc GR . . . . H36B H 0.548480 0.603367 0.582850 0.043 Uiso 1 1 calc GR . . . . H36C H 0.574749 0.645313 0.700247 0.043 Uiso 1 1 calc GR . . . . C110 C 0.7817(3) 0.20220(19) 0.76865(17) 0.0209(4) Uani 1 1 d . . . . . C210 C 0.2487(3) 0.34790(18) 0.67536(17) 0.0190(4) Uani 1 1 d . . . . . C1 C 0.830(3) 1.0330(12) 0.9702(10) 0.105(8) Uani 0.290(12) 1 d D . P A 1 H1A H 0.949549 1.041357 0.963013 0.126 Uiso 0.290(12) 1 calc R . P A 1 H1B H 0.769450 1.076744 0.937602 0.126 Uiso 0.290(12) 1 calc R . P A 1 Cl1 Cl 0.751(2) 0.8895(9) 0.8978(9) 0.146(5) Uani 0.290(12) 1 d D U P A 1 Cl2 Cl 0.832(3) 1.1010(17) 1.0854(6) 0.208(6) Uani 0.290(12) 1 d D U P A 1 C1A C 0.709(2) 1.0561(8) 0.9645(7) 0.148(3) Uani 0.710(12) 1 d D U P A 2 H1AA H 0.788912 1.080674 0.931126 0.178 Uiso 0.710(12) 1 calc R . P A 2 H1AB H 0.595637 1.070426 0.939192 0.178 Uiso 0.710(12) 1 calc R . P A 2 Cl1A Cl 0.7009(11) 0.9053(4) 0.9202(4) 0.166(2) Uani 0.710(12) 1 d D U P A 2 Cl2A Cl 0.7577(10) 1.1423(3) 1.0782(4) 0.176(2) Uani 0.710(12) 1 d D U P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Zn1 0.01424(13) 0.01554(13) 0.01859(14) 0.00352(10) 0.00575(9) 0.00277(9) O11 0.0251(8) 0.0219(8) 0.0193(8) 0.0039(6) 0.0064(6) 0.0080(6) O12 0.0378(9) 0.0296(9) 0.0234(9) 0.0092(7) -0.0024(7) 0.0085(7) O21 0.0152(7) 0.0192(7) 0.0229(8) 0.0027(6) 0.0042(6) 0.0025(6) O22 0.0150(7) 0.0212(8) 0.0377(9) 0.0075(7) 0.0054(6) 0.0026(6) N1 0.0126(8) 0.0158(8) 0.0200(9) 0.0046(7) 0.0058(7) 0.0012(6) N2 0.0176(8) 0.0174(9) 0.0196(9) 0.0064(7) 0.0071(7) 0.0040(7) N31 0.0159(8) 0.0208(9) 0.0303(10) 0.0129(8) 0.0070(7) 0.0056(7) N32 0.0140(8) 0.0191(9) 0.0260(10) 0.0081(8) 0.0087(7) 0.0054(7) C11 0.0130(9) 0.0166(10) 0.0211(10) 0.0050(8) 0.0046(8) -0.0001(7) C12 0.0184(10) 0.0162(10) 0.0275(11) 0.0086(9) 0.0043(8) 0.0017(8) C13 0.0202(10) 0.0128(9) 0.0309(12) 0.0063(9) 0.0096(9) 0.0024(8) C14 0.0170(9) 0.0138(9) 0.0239(11) 0.0038(8) 0.0085(8) 0.0000(8) C15 0.0258(11) 0.0154(10) 0.0245(11) 0.0026(9) 0.0102(9) 0.0004(8) C16 0.0286(11) 0.0200(11) 0.0198(11) 0.0021(9) 0.0072(9) -0.0022(9) C17 0.0197(10) 0.0244(11) 0.0229(11) 0.0086(9) 0.0040(8) 0.0007(8) C18 0.0176(10) 0.0184(10) 0.0228(11) 0.0054(9) 0.0063(8) 0.0026(8) C19 0.0129(9) 0.0142(9) 0.0198(10) 0.0034(8) 0.0065(8) -0.0003(7) C21 0.0195(10) 0.0158(10) 0.0226(11) 0.0090(8) 0.0077(8) 0.0055(8) C22 0.0181(10) 0.0249(11) 0.0283(12) 0.0117(10) 0.0102(9) 0.0072(8) C23 0.0260(11) 0.0247(11) 0.0257(12) 0.0098(9) 0.0153(9) 0.0115(9) C24 0.0271(11) 0.0197(10) 0.0205(11) 0.0078(9) 0.0101(9) 0.0084(9) C25 0.0332(12) 0.0231(11) 0.0210(11) 0.0048(9) 0.0114(9) 0.0107(9) C26 0.0368(13) 0.0230(12) 0.0187(11) 0.0015(9) 0.0045(10) 0.0051(10) C27 0.0247(11) 0.0247(12) 0.0240(12) 0.0054(10) 0.0043(9) 0.0008(9) C28 0.0209(10) 0.0243(11) 0.0219(11) 0.0042(9) 0.0074(9) 0.0036(9) C29 0.0215(10) 0.0162(10) 0.0198(10) 0.0050(8) 0.0064(8) 0.0039(8) C31 0.0166(10) 0.0257(12) 0.0393(14) 0.0170(11) 0.0078(9) 0.0056(9) C32 0.0250(13) 0.0378(15) 0.094(3) 0.0408(17) 0.0224(14) 0.0088(11) C33 0.0223(13) 0.0461(18) 0.143(4) 0.064(2) 0.0060(17) 0.0033(12) C34 0.0242(11) 0.0276(12) 0.0448(15) 0.0228(11) 0.0122(10) 0.0091(9) C35 0.0160(9) 0.0215(10) 0.0184(10) 0.0061(8) 0.0051(8) 0.0036(8) C36 0.0179(10) 0.0339(13) 0.0413(14) 0.0213(11) 0.0109(10) 0.0100(9) C110 0.0157(9) 0.0203(10) 0.0210(11) 0.0038(9) 0.0022(8) 0.0010(8) C210 0.0178(10) 0.0127(9) 0.0256(11) 0.0066(8) 0.0058(8) 0.0031(8) C1 0.17(2) 0.056(9) 0.081(12) 0.040(9) -0.032(13) 0.002(11) Cl1 0.220(9) 0.110(5) 0.077(4) 0.053(4) -0.082(6) -0.017(5) Cl2 0.282(11) 0.219(10) 0.053(4) 0.014(5) -0.012(5) -0.041(9) C1A 0.229(9) 0.123(4) 0.106(4) 0.092(4) -0.027(6) -0.037(6) Cl1A 0.292(6) 0.108(2) 0.110(3) 0.075(2) 0.002(3) -0.017(3) Cl2A 0.296(6) 0.104(2) 0.134(3) 0.0676(19) 0.012(3) 0.031(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 O11 Zn1 O21 127.51(7) . . ? O11 Zn1 N1 79.24(7) . . ? O11 Zn1 N2 87.39(6) . . ? O21 Zn1 N1 94.90(6) . . ? O21 Zn1 N2 77.66(6) . . ? N1 Zn1 N2 156.16(7) . . ? N32 Zn1 O11 113.29(7) . . ? N32 Zn1 O21 119.12(7) . . ? N32 Zn1 N1 99.17(7) . . ? N32 Zn1 N2 104.25(7) . . ? C110 O11 Zn1 117.79(14) . . ? C210 O21 Zn1 117.65(14) . . ? C11 N1 Zn1 110.99(14) . . ? C11 N1 C19 118.76(17) . . ? C19 N1 Zn1 130.03(14) . . ? C21 N2 Zn1 110.80(14) . . ? C21 N2 C29 119.16(18) . . ? C29 N2 Zn1 128.70(14) . . ? C31 N31 C34 112.08(17) . . ? C35 N31 C31 122.10(18) . . ? C35 N31 C34 125.50(18) . . ? Zn1 N32 H32 112.0(19) . . ? C35 N32 Zn1 130.63(15) . . ? C35 N32 H32 116.8(19) . . ? N1 C11 C12 123.4(2) . . ? N1 C11 C110 115.93(18) . . ? C12 C11 C110 120.64(19) . . ? C11 C12 H12 120.5 . . ? C13 C12 C11 119.1(2) . . ? C13 C12 H12 120.5 . . ? C12 C13 H13 120.3 . . ? C12 C13 C14 119.44(19) . . ? C14 C13 H13 120.3 . . ? C13 C14 C15 123.25(19) . . ? C13 C14 C19 118.3(2) . . ? C15 C14 C19 118.4(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 C14 120.5(2) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 119.7 . . ? C15 C16 C17 120.7(2) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 119.8 . . ? C18 C17 C16 120.4(2) . . ? C18 C17 H17 119.8 . . ? C17 C18 H18 119.9 . . ? C17 C18 C19 120.2(2) . . ? C19 C18 H18 119.9 . . ? N1 C19 C14 120.98(19) . . ? N1 C19 C18 119.31(18) . . ? C18 C19 C14 119.7(2) . . ? N2 C21 C22 123.2(2) . . ? N2 C21 C210 114.94(18) . . ? C22 C21 C210 121.89(19) . . ? C21 C22 H22 120.6 . . ? C23 C22 C21 118.9(2) . . ? C23 C22 H22 120.6 . . ? C22 C23 H23 120.2 . . ? C22 C23 C24 119.6(2) . . ? C24 C23 H23 120.2 . . ? C23 C24 C25 123.2(2) . . ? C23 C24 C29 118.1(2) . . ? C25 C24 C29 118.8(2) . . ? C24 C25 H25 119.9 . . ? C26 C25 C24 120.2(2) . . ? C26 C25 H25 119.9 . . ? 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(2) . . ? C28 C27 H27 119.6 . . ? C27 C28 H28 120.1 . . ? C27 C28 C29 119.8(2) . . ? C29 C28 H28 120.1 . . ? N2 C29 C24 121.05(19) . . ? N2 C29 C28 119.12(19) . . ? C28 C29 C24 119.8(2) . . ? N31 C31 H31A 110.9 . . ? N31 C31 H31B 110.9 . . ? N31 C31 C32 104.08(19) . . ? H31A C31 H31B 109.0 . . ? C32 C31 H31A 110.9 . . ? C32 C31 H31B 110.9 . . ? C31 C32 H32A 110.1 . . ? C31 C32 H32B 110.1 . . ? H32A C32 H32B 108.5 . . ? C33 C32 C31 107.8(2) . . ? C33 C32 H32A 110.1 . . ? C33 C32 H32B 110.1 . . ? C32 C33 H33A 109.8 . . ? C32 C33 H33B 109.8 . . ? C32 C33 C34 109.2(2) . . ? H33A C33 H33B 108.3 . . ? C34 C33 H33A 109.8 . . ? C34 C33 H33B 109.8 . . ? N31 C34 C33 104.04(19) . . ? N31 C34 H34A 110.9 . . ? N31 C34 H34B 110.9 . . ? C33 C34 H34A 110.9 . . ? C33 C34 H34B 110.9 . . ? H34A C34 H34B 109.0 . . ? N31 C35 C36 117.1(2) . . ? N32 C35 N31 123.87(19) . . ? N32 C35 C36 119.07(19) . . ? 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 . . ? O11 C110 C11 115.65(19) . . ? O12 C110 O11 126.3(2) . . ? O12 C110 C11 118.00(19) . . ? O21 C210 C21 115.56(18) . . ? O22 C210 O21 125.6(2) . . ? O22 C210 C21 118.80(19) . . ? H1A C1 H1B 106.2 . . ? Cl1 C1 H1A 105.9 . . ? Cl1 C1 H1B 105.9 . . ? Cl2 C1 H1A 105.9 . . ? Cl2 C1 H1B 105.9 . . ? Cl2 C1 Cl1 125.6(10) . . ? H1AA C1A H1AB 106.5 . . ? Cl1A C1A H1AA 106.4 . . ? Cl1A C1A H1AB 106.4 . . ? Cl2A C1A H1AA 106.4 . . ? Cl2A C1A H1AB 106.4 . . ? Cl2A C1A Cl1A 123.6(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 Zn1 O11 2.0105(16) . ? Zn1 O21 2.0191(15) . ? Zn1 N1 2.1578(17) . ? Zn1 N2 2.1763(17) . ? Zn1 N32 1.9952(18) . ? O11 C110 1.273(3) . ? O12 C110 1.230(3) . ? O21 C210 1.280(3) . ? O22 C210 1.233(3) . ? N1 C11 1.317(3) . ? N1 C19 1.373(3) . ? N2 C21 1.319(3) . ? N2 C29 1.372(3) . ? N31 C31 1.466(3) . ? N31 C34 1.478(3) . ? N31 C35 1.337(3) . ? N32 H32 0.79(3) . ? N32 C35 1.301(3) . ? C11 C12 1.410(3) . ? C11 C110 1.529(3) . ? C12 H12 0.9300 . ? C12 C13 1.362(3) . ? C13 H13 0.9300 . ? C13 C14 1.410(3) . ? C14 C15 1.419(3) . ? C14 C19 1.423(3) . ? C15 H15 0.9300 . ? C15 C16 1.363(3) . ? C16 H16 0.9300 . ? C16 C17 1.410(3) . ? C17 H17 0.9300 . ? C17 C18 1.369(3) . ? C18 H18 0.9300 . ? C18 C19 1.409(3) . ? C21 C22 1.409(3) . ? C21 C210 1.523(3) . ? C22 H22 0.9300 . ? C22 C23 1.369(3) . ? C23 H23 0.9300 . ? C23 C24 1.413(3) . ? C24 C25 1.419(3) . ? C24 C29 1.420(3) . ? C25 H25 0.9300 . ? C25 C26 1.365(4) . ? C26 H26 0.9300 . ? C26 C27 1.411(3) . ? C27 H27 0.9300 . ? C27 C28 1.367(3) . ? C28 H28 0.9300 . ? C28 C29 1.413(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 C32 1.512(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C33 1.450(4) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 C34 1.486(4) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.503(3) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 Cl1 1.699(10) . ? C1 Cl2 1.560(11) . ? C1A H1AA 0.9700 . ? C1A H1AB 0.9700 . ? C1A Cl1A 1.733(9) . ? C1A Cl2A 1.553(9) . ? 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 O22 0.79(3) 2.27(3) 3.038(2) 164(3) 1_655 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Zn1 O11 C110 O12 -173.63(18) . . . . ? Zn1 O11 C110 C11 5.3(2) . . . . ? Zn1 O21 C210 O22 -170.80(17) . . . . ? Zn1 O21 C210 C21 10.8(2) . . . . ? Zn1 N1 C11 C12 -174.66(16) . . . . ? Zn1 N1 C11 C110 5.7(2) . . . . ? Zn1 N1 C19 C14 172.47(14) . . . . ? Zn1 N1 C19 C18 -8.1(3) . . . . ? Zn1 N2 C21 C22 165.42(17) . . . . ? Zn1 N2 C21 C210 -15.6(2) . . . . ? Zn1 N2 C29 C24 -164.13(16) . . . . ? Zn1 N2 C29 C28 16.3(3) . . . . ? Zn1 N32 C35 N31 167.31(17) . . . . ? Zn1 N32 C35 C36 -11.9(3) . . . . ? N1 C11 C12 C13 0.8(3) . . . . ? N1 C11 C110 O11 -7.6(3) . . . . ? N1 C11 C110 O12 171.44(19) . . . . ? N2 C21 C22 C23 1.4(3) . . . . ? N2 C21 C210 O21 4.5(3) . . . . ? N2 C21 C210 O22 -174.07(19) . . . . ? N31 C31 C32 C33 13.4(4) . . . . ? C11 N1 C19 C14 -1.5(3) . . . . ? C11 N1 C19 C18 177.93(18) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C12 C11 C110 O11 172.80(19) . . . . ? C12 C11 C110 O12 -8.2(3) . . . . ? C12 C13 C14 C15 179.6(2) . . . . ? C12 C13 C14 C19 -0.2(3) . . . . ? C13 C14 C15 C16 179.1(2) . . . . ? C13 C14 C19 N1 1.4(3) . . . . ? C13 C14 C19 C18 -178.05(18) . . . . ? C14 C15 C16 C17 -0.7(3) . . . . ? C15 C14 C19 N1 -178.36(18) . . . . ? C15 C14 C19 C18 2.2(3) . . . . ? C15 C16 C17 C18 1.6(3) . . . . ? C16 C17 C18 C19 -0.5(3) . . . . ? C17 C18 C19 N1 179.15(19) . . . . ? C17 C18 C19 C14 -1.4(3) . . . . ? C19 N1 C11 C12 0.4(3) . . . . ? C19 N1 C11 C110 -179.18(17) . . . . ? C19 C14 C15 C16 -1.1(3) . . . . ? C21 N2 C29 C24 1.4(3) . . . . ? C21 N2 C29 C28 -178.2(2) . . . . ? C21 C22 C23 C24 0.9(3) . . . . ? C22 C21 C210 O21 -176.6(2) . . . . ? C22 C21 C210 O22 4.9(3) . . . . ? C22 C23 C24 C25 178.5(2) . . . . ? C22 C23 C24 C29 -1.9(3) . . . . ? C23 C24 C25 C26 -179.8(2) . . . . ? C23 C24 C29 N2 0.8(3) . . . . ? C23 C24 C29 C28 -179.6(2) . . . . ? C24 C25 C26 C27 -0.6(4) . . . . ? C25 C24 C29 N2 -179.6(2) . . . . ? C25 C24 C29 C28 0.0(3) . . . . ? C25 C26 C27 C28 -0.1(4) . . . . ? C26 C27 C28 C29 0.8(4) . . . . ? C27 C28 C29 N2 178.9(2) . . . . ? C27 C28 C29 C24 -0.7(3) . . . . ? C29 N2 C21 C22 -2.5(3) . . . . ? C29 N2 C21 C210 176.42(18) . . . . ? C29 C24 C25 C26 0.6(3) . . . . ? C31 N31 C34 C33 -5.2(3) . . . . ? C31 N31 C35 N32 -6.3(4) . . . . ? C31 N31 C35 C36 173.0(2) . . . . ? C31 C32 C33 C34 -17.4(5) . . . . ? C32 C33 C34 N31 13.9(4) . . . . ? C34 N31 C31 C32 -4.9(3) . . . . ? C34 N31 C35 N32 -179.3(2) . . . . ? C34 N31 C35 C36 -0.1(3) . . . . ? C35 N31 C31 C32 -178.7(2) . . . . ? C35 N31 C34 C33 168.4(3) . . . . ? C110 C11 C12 C13 -179.60(19) . . . . ? C210 C21 C22 C23 -177.5(2) . . . . ?