#------------------------------------------------------------------------------ #$Date: 2020-05-14 06:08:43 +0300 (Thu, 14 May 2020) $ #$Revision: 252047 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240522.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_7240522 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 'C30 H18 N3 O6 Zn, C4 H10 N, C2 H3 N' _chemical_formula_sum 'C36 H31 N5 O6 Zn' _chemical_formula_weight 695.03 _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 geom _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 91.334(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.2473(7) _cell_length_b 14.3337(9) _cell_length_c 17.9869(12) _cell_measurement_reflns_used 3361 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 26.1120 _cell_measurement_theta_min 3.0370 _cell_volume 3414.5(4) _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 -101.00 -56.00 1.00 175.00 -- -14.36 178.00-150.00 45 2 \w -102.00 -75.00 1.00 175.00 -- -14.36 178.00 90.00 27 3 \w -40.00 58.00 1.00 175.00 -- -14.36 19.00-150.00 98 4 \w -30.00 16.00 1.00 175.00 -- -14.36 37.00 -30.00 46 ; _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 0.0125234000 _diffrn_orient_matrix_UB_12 -0.0422967000 _diffrn_orient_matrix_UB_13 -0.0180662000 _diffrn_orient_matrix_UB_21 0.0299018000 _diffrn_orient_matrix_UB_22 -0.0134854000 _diffrn_orient_matrix_UB_23 0.0314046000 _diffrn_orient_matrix_UB_31 -0.0426246000 _diffrn_orient_matrix_UB_32 -0.0218735000 _diffrn_orient_matrix_UB_33 0.0155943000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0551 _diffrn_reflns_av_unetI/netI 0.0954 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 17656 _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 27.500 _diffrn_reflns_theta_min 2.363 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.772 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.65806 _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 1.352 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1440 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.500 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 434 _refine_ls_number_reflns 7838 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.991 _refine_ls_R_factor_all 0.1121 _refine_ls_R_factor_gt 0.0545 _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^)+(0.0501P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1085 _refine_ls_wR_factor_ref 0.1331 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4598 _reflns_number_total 7838 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03192e3.cif _cod_data_source_block 8monoclinic _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 7240522 _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 0.962 _shelx_estimated_absorpt_t_min 0.861 _shelx_res_file ; TITL mob606 in P2(1)/n mob606.res created by SHELXL-2018/3 at 11:19:21 on 16-Dec-2019 CELL 0.71073 13.2473 14.3337 17.9869 90 91.334 90 ZERR 4 0.0007 0.0009 0.0012 0 0.005 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Zn UNIT 144 124 20 24 4 EQIV $1 1-X,1-Y,1-Z L.S. 10 PLAN 10 SIZE 0.2 0.15 0.05 MPLA N1 C11 C12 C13 C14 C15 C16 C17 C18 C19 MPLA N2 C21 C22 C23 C24 C25 C26 C27 C28 C29 MPLA N3 C31 C32 C33 C34 C35 C36 C37 C38 C39 MPLA N1 C11 C12 C13 C14 C15 C16 C17 C18 C19 HTAB N4 O22 HTAB N4 O32_$1 MORE -1 HTAB 2.00000 BOND $H CONF LIST 6 fmap 2 acta MERG 2 SHEL 30 0.7696 REM REM REM WGHT 0.050100 FVAR 0.78236 ZN1 5 0.738119 0.678467 0.472512 11.00000 0.02597 0.03349 = 0.03923 -0.00046 -0.00113 -0.00080 O11 4 0.851999 0.737619 0.529750 11.00000 0.02757 0.04070 = 0.04170 0.00346 -0.00804 -0.00010 O12 4 0.893075 0.853422 0.607369 11.00000 0.03468 0.07442 = 0.05408 -0.01488 -0.01142 -0.01413 O21 4 0.643580 0.637539 0.390027 11.00000 0.03487 0.02926 = 0.03879 0.00073 -0.00590 -0.00295 O22 4 0.545960 0.670207 0.291606 11.00000 0.03339 0.04002 = 0.03866 -0.00398 -0.00680 -0.00728 O31 4 0.680668 0.581016 0.544713 11.00000 0.03562 0.03501 = 0.04063 0.00474 0.00665 0.00382 O32 4 0.679177 0.429676 0.573039 11.00000 0.04706 0.03600 = 0.05402 0.00623 0.01749 -0.00150 N1 3 0.658032 0.789796 0.529679 11.00000 0.03203 0.03142 = 0.02836 0.00340 0.00045 -0.00340 N2 3 0.747460 0.797765 0.371874 11.00000 0.02448 0.03336 = 0.02958 -0.00064 0.00089 -0.00221 N3 3 0.832505 0.555591 0.451304 11.00000 0.02337 0.03334 = 0.02995 -0.00077 -0.00414 0.00071 N4 3 0.472526 0.499606 0.339538 11.00000 0.03618 0.03748 = 0.04614 -0.00866 0.00847 -0.00823 AFIX 23 H4A 2 0.504836 0.548821 0.321538 11.00000 -1.20000 H4B 2 0.431763 0.519193 0.374948 11.00000 -1.20000 AFIX 0 N5 3 0.301072 0.872495 0.299981 11.00000 0.11444 0.04997 = 0.09185 -0.00206 -0.02718 -0.00818 C11 1 0.722742 0.842259 0.567294 11.00000 0.03356 0.03233 = 0.03010 -0.00002 -0.00421 -0.00731 C12 1 0.695795 0.923733 0.604470 11.00000 0.04578 0.03745 = 0.04092 0.00015 -0.00739 -0.01105 AFIX 43 H12 2 0.744559 0.959213 0.629487 11.00000 -1.20000 AFIX 0 C13 1 0.597179 0.950546 0.603609 11.00000 0.05269 0.03553 = 0.05184 -0.00610 -0.00091 0.00250 AFIX 43 H13 2 0.578058 1.005038 0.627560 11.00000 -1.20000 AFIX 0 C14 1 0.524353 0.895221 0.566214 11.00000 0.03934 0.03752 = 0.03473 0.00136 0.00029 0.00306 C15 1 0.420196 0.918501 0.563841 11.00000 0.04439 0.05055 = 0.05948 -0.00752 0.00399 0.01326 AFIX 43 H15 2 0.397707 0.972073 0.587467 11.00000 -1.20000 AFIX 0 C16 1 0.353319 0.862093 0.526835 11.00000 0.02985 0.06849 = 0.06320 -0.00276 0.00030 0.00916 AFIX 43 H16 2 0.285128 0.877583 0.525392 11.00000 -1.20000 AFIX 0 C17 1 0.385606 0.781235 0.490971 11.00000 0.03053 0.05348 = 0.04687 -0.00526 0.00092 -0.00212 AFIX 43 H17 2 0.338725 0.743366 0.466268 11.00000 -1.20000 AFIX 0 C18 1 0.485585 0.757411 0.491940 11.00000 0.03190 0.03871 = 0.03917 -0.00327 0.00441 -0.00319 AFIX 43 H18 2 0.506447 0.703485 0.467994 11.00000 -1.20000 AFIX 0 C19 1 0.556848 0.814411 0.529124 11.00000 0.02841 0.03488 = 0.02620 0.00395 0.00179 0.00023 C21 1 0.664959 0.784093 0.329482 11.00000 0.02395 0.03383 = 0.02887 -0.00291 0.00350 0.00073 C22 1 0.624728 0.849747 0.279928 11.00000 0.03272 0.04004 = 0.04333 0.00524 -0.00823 -0.00323 AFIX 43 H22 2 0.567657 0.835836 0.250938 11.00000 -1.20000 AFIX 0 C23 1 0.670105 0.934293 0.274621 11.00000 0.03586 0.04030 = 0.04578 0.01306 -0.00916 -0.00202 AFIX 43 H23 2 0.643096 0.979789 0.243119 11.00000 -1.20000 AFIX 0 C24 1 0.758728 0.952607 0.317363 11.00000 0.03005 0.03809 = 0.03874 0.00045 0.00411 -0.00424 C25 1 0.811199 1.038531 0.313307 11.00000 0.04261 0.03942 = 0.05313 0.01059 0.00162 -0.00792 AFIX 43 H25 2 0.786283 1.085762 0.282547 11.00000 -1.20000 AFIX 0 C26 1 0.897971 1.052582 0.354143 11.00000 0.04537 0.04826 = 0.04734 0.00207 0.00488 -0.02110 AFIX 43 H26 2 0.931874 1.109258 0.351506 11.00000 -1.20000 AFIX 0 C27 1 0.935756 0.980887 0.400191 11.00000 0.03949 0.06181 = 0.04175 0.00547 -0.00618 -0.01983 AFIX 43 H27 2 0.995459 0.990463 0.427344 11.00000 -1.20000 AFIX 0 C28 1 0.886883 0.897571 0.405981 11.00000 0.03101 0.05305 = 0.03542 0.00774 -0.00179 -0.01131 AFIX 43 H28 2 0.913157 0.851108 0.436896 11.00000 -1.20000 AFIX 0 C29 1 0.796274 0.881992 0.364927 11.00000 0.02604 0.03823 = 0.03039 -0.00388 0.00583 -0.00379 C31 1 0.804670 0.483100 0.491713 11.00000 0.02494 0.03615 = 0.02955 -0.00125 -0.00563 -0.00251 C32 1 0.854195 0.396606 0.490976 11.00000 0.02852 0.03410 = 0.04163 0.00370 -0.00104 -0.00368 AFIX 43 H32 2 0.831127 0.347458 0.519750 11.00000 -1.20000 AFIX 0 C33 1 0.936233 0.385257 0.447815 11.00000 0.02799 0.03225 = 0.03837 -0.00088 -0.00699 0.00105 AFIX 43 H33 2 0.970674 0.328729 0.447405 11.00000 -1.20000 AFIX 0 C34 1 0.968152 0.460144 0.403892 11.00000 0.02206 0.03717 = 0.03201 -0.00555 -0.00598 0.00005 C35 1 1.052247 0.453001 0.355896 11.00000 0.02623 0.04123 = 0.03901 -0.00439 -0.00282 0.00263 AFIX 43 H35 2 1.089170 0.397905 0.353968 11.00000 -1.20000 AFIX 0 C36 1 1.078112 0.526958 0.313074 11.00000 0.03000 0.04767 = 0.04208 -0.00666 0.00243 -0.00331 AFIX 43 H36 2 1.132971 0.522116 0.281970 11.00000 -1.20000 AFIX 0 C37 1 1.023276 0.610275 0.315183 11.00000 0.04217 0.04306 = 0.04252 0.00388 0.00610 -0.00739 AFIX 43 H37 2 1.041959 0.659952 0.285222 11.00000 -1.20000 AFIX 0 C38 1 0.942583 0.619766 0.360657 11.00000 0.03322 0.03543 = 0.04198 0.00110 0.00196 0.00210 AFIX 43 H38 2 0.906673 0.675489 0.361565 11.00000 -1.20000 AFIX 0 C39 1 0.914205 0.544590 0.406118 11.00000 0.02304 0.03366 = 0.03112 -0.00249 -0.00294 -0.00266 C41 1 0.412604 0.452995 0.279041 11.00000 0.06036 0.04708 = 0.05755 -0.01687 0.00139 -0.00911 AFIX 23 H41A 2 0.430032 0.477551 0.230754 11.00000 -1.20000 H41B 2 0.340789 0.461435 0.285995 11.00000 -1.20000 AFIX 0 C42 1 0.441307 0.352059 0.285798 11.00000 0.08907 0.05351 = 0.10374 -0.02769 -0.00645 0.00118 AFIX 23 H42A 2 0.396715 0.319913 0.319296 11.00000 -1.20000 H42B 2 0.437350 0.321726 0.237611 11.00000 -1.20000 AFIX 0 C43 1 0.545670 0.351218 0.315484 11.00000 0.07826 0.05196 = 0.08231 -0.00048 0.02615 0.01206 AFIX 23 H43A 2 0.593585 0.361905 0.276417 11.00000 -1.20000 H43B 2 0.561380 0.292444 0.339852 11.00000 -1.20000 AFIX 0 C44 1 0.546467 0.431184 0.370841 11.00000 0.05263 0.04097 = 0.07646 0.01287 0.00023 -0.00470 AFIX 23 H44A 2 0.526156 0.409839 0.419434 11.00000 -1.20000 H44B 2 0.613219 0.458699 0.375414 11.00000 -1.20000 AFIX 0 C51 1 0.302954 0.794894 0.288809 11.00000 0.04901 0.04515 = 0.05064 0.00571 -0.01330 -0.00666 C52 1 0.303527 0.696235 0.273778 11.00000 0.04502 0.04345 = 0.06014 0.00369 0.00186 0.00165 AFIX 137 H52A 2 0.303290 0.662442 0.319854 11.00000 -1.50000 H52B 2 0.363021 0.680469 0.247016 11.00000 -1.50000 H52C 2 0.244653 0.680013 0.244443 11.00000 -1.50000 AFIX 0 C110 1 0.832884 0.809521 0.568711 11.00000 0.03404 0.04150 = 0.03370 0.01045 -0.00523 -0.00688 C210 1 0.614016 0.690308 0.337351 11.00000 0.02459 0.03439 = 0.03401 -0.00371 0.00356 0.00353 C310 1 0.713809 0.499361 0.541135 11.00000 0.03041 0.03734 = 0.03589 -0.00435 -0.00283 -0.00115 HKLF 4 REM mob606 in P2(1)/n REM wR2 = 0.1331, GooF = S = 0.991, Restrained GooF = 0.991 for all data REM R1 = 0.0545 for 4598 Fo > 4sig(Fo) and 0.1121 for all 7838 data REM 434 parameters refined using 0 restraints END WGHT 0.0501 0.0000 REM Instructions for potential hydrogen bonds HTAB N4 O21 HTAB N4 O22 HTAB N4 O31_$1 HTAB N4 O32_$1 HTAB C18 O21 HTAB C28 O11 HTAB C44 O21 HTAB C52 O32_$1 EQIV $2 x-1/2, -y+3/2, z-1/2 HTAB C52 O12_$2 HTAB C52 O22 REM Highest difference peak 0.500, deepest hole -0.391, 1-sigma level 0.069 Q1 1 0.7411 0.7660 0.4393 11.00000 0.05 0.50 Q2 1 0.7419 0.7549 0.4857 11.00000 0.05 0.47 Q3 1 0.7897 0.6764 0.5788 11.00000 0.05 0.44 Q4 1 0.2612 1.0334 0.5273 11.00000 0.05 0.42 Q5 1 0.8076 0.6236 0.4761 11.00000 0.05 0.36 Q6 1 0.7065 0.6014 0.5127 11.00000 0.05 0.31 Q7 1 0.4936 0.3832 0.2494 11.00000 0.05 0.28 Q8 1 0.3796 0.3038 0.1293 11.00000 0.05 0.27 Q9 1 0.6189 0.3835 0.3619 11.00000 0.05 0.27 Q10 1 0.2321 0.8612 0.3286 11.00000 0.05 0.27 ; _shelx_res_checksum 76832 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 0.73812(3) 0.67847(3) 0.47251(2) 0.03293(13) Uani 1 1 d . . . . . O11 O 0.85200(14) 0.73762(17) 0.52975(13) 0.0368(6) Uani 1 1 d . . . . . O12 O 0.89308(17) 0.8534(2) 0.60737(14) 0.0546(7) Uani 1 1 d . . . . . O21 O 0.64358(15) 0.63754(16) 0.39003(12) 0.0344(5) Uani 1 1 d . . . . . O22 O 0.54596(15) 0.67021(16) 0.29161(12) 0.0375(6) Uani 1 1 d . . . . . O31 O 0.68067(15) 0.58102(16) 0.54471(12) 0.0370(6) Uani 1 1 d . . . . . O32 O 0.67918(17) 0.42968(17) 0.57304(14) 0.0454(6) Uani 1 1 d . . . . . N1 N 0.65803(18) 0.78980(19) 0.52968(14) 0.0306(6) Uani 1 1 d . . . . . N2 N 0.74746(17) 0.79776(18) 0.37187(14) 0.0291(6) Uani 1 1 d . . . . . N3 N 0.83251(16) 0.55559(19) 0.45130(14) 0.0290(6) Uani 1 1 d . . . . . N4 N 0.47253(19) 0.4996(2) 0.33954(16) 0.0398(7) Uani 1 1 d . . . . . H4A H 0.504836 0.548821 0.321538 0.048 Uiso 1 1 calc R . . . . H4B H 0.431763 0.519193 0.374948 0.048 Uiso 1 1 calc R . . . . N5 N 0.3011(3) 0.8725(3) 0.3000(2) 0.0859(13) Uani 1 1 d . . . . . C11 C 0.7227(2) 0.8423(2) 0.56729(18) 0.0321(8) Uani 1 1 d . . . . . C12 C 0.6958(3) 0.9237(2) 0.6045(2) 0.0415(9) Uani 1 1 d . . . . . H12 H 0.744559 0.959213 0.629487 0.050 Uiso 1 1 calc R . . . . C13 C 0.5972(3) 0.9505(3) 0.6036(2) 0.0467(10) Uani 1 1 d . . . . . H13 H 0.578058 1.005038 0.627560 0.056 Uiso 1 1 calc R . . . . C14 C 0.5244(2) 0.8952(2) 0.56621(19) 0.0372(8) Uani 1 1 d . . . . . C15 C 0.4202(3) 0.9185(3) 0.5638(2) 0.0514(10) Uani 1 1 d . . . . . H15 H 0.397707 0.972073 0.587467 0.062 Uiso 1 1 calc R . . . . C16 C 0.3533(3) 0.8621(3) 0.5268(2) 0.0539(11) Uani 1 1 d . . . . . H16 H 0.285128 0.877583 0.525392 0.065 Uiso 1 1 calc R . . . . C17 C 0.3856(2) 0.7812(3) 0.4910(2) 0.0436(9) Uani 1 1 d . . . . . H17 H 0.338725 0.743366 0.466268 0.052 Uiso 1 1 calc R . . . . C18 C 0.4856(2) 0.7574(3) 0.49194(19) 0.0365(8) Uani 1 1 d . . . . . H18 H 0.506447 0.703485 0.467994 0.044 Uiso 1 1 calc R . . . . C19 C 0.5568(2) 0.8144(2) 0.52912(17) 0.0298(7) Uani 1 1 d . . . . . C21 C 0.6650(2) 0.7841(2) 0.32948(17) 0.0288(7) Uani 1 1 d . . . . . C22 C 0.6247(2) 0.8497(2) 0.2799(2) 0.0388(9) Uani 1 1 d . . . . . H22 H 0.567657 0.835836 0.250938 0.047 Uiso 1 1 calc R . . . . C23 C 0.6701(2) 0.9343(3) 0.2746(2) 0.0408(9) Uani 1 1 d . . . . . H23 H 0.643096 0.979789 0.243119 0.049 Uiso 1 1 calc R . . . . C24 C 0.7587(2) 0.9526(2) 0.31736(19) 0.0356(8) Uani 1 1 d . . . . . C25 C 0.8112(2) 1.0385(3) 0.3133(2) 0.0450(9) Uani 1 1 d . . . . . H25 H 0.786283 1.085762 0.282547 0.054 Uiso 1 1 calc R . . . . C26 C 0.8980(3) 1.0526(3) 0.3541(2) 0.0469(10) Uani 1 1 d . . . . . H26 H 0.931874 1.109258 0.351506 0.056 Uiso 1 1 calc R . . . . C27 C 0.9358(3) 0.9809(3) 0.4002(2) 0.0478(10) Uani 1 1 d . . . . . H27 H 0.995459 0.990463 0.427344 0.057 Uiso 1 1 calc R . . . . C28 C 0.8869(2) 0.8976(3) 0.40598(19) 0.0399(9) Uani 1 1 d . . . . . H28 H 0.913157 0.851108 0.436896 0.048 Uiso 1 1 calc R . . . . C29 C 0.7963(2) 0.8820(2) 0.36493(18) 0.0315(8) Uani 1 1 d . . . . . C31 C 0.8047(2) 0.4831(2) 0.49171(18) 0.0303(7) Uani 1 1 d . . . . . C32 C 0.8542(2) 0.3966(2) 0.49098(19) 0.0348(8) Uani 1 1 d . . . . . H32 H 0.831127 0.347458 0.519750 0.042 Uiso 1 1 calc R . . . . C33 C 0.9362(2) 0.3853(2) 0.44782(18) 0.0330(8) Uani 1 1 d . . . . . H33 H 0.970674 0.328729 0.447405 0.040 Uiso 1 1 calc R . . . . C34 C 0.9682(2) 0.4601(2) 0.40389(18) 0.0305(8) Uani 1 1 d . . . . . C35 C 1.0522(2) 0.4530(2) 0.35590(19) 0.0355(8) Uani 1 1 d . . . . . H35 H 1.089170 0.397905 0.353968 0.043 Uiso 1 1 calc R . . . . C36 C 1.0781(2) 0.5270(3) 0.3131(2) 0.0399(9) Uani 1 1 d . . . . . H36 H 1.132971 0.522116 0.281970 0.048 Uiso 1 1 calc R . . . . C37 C 1.0233(2) 0.6103(3) 0.3152(2) 0.0425(9) Uani 1 1 d . . . . . H37 H 1.041959 0.659952 0.285222 0.051 Uiso 1 1 calc R . . . . C38 C 0.9426(2) 0.6198(2) 0.36066(19) 0.0369(8) Uani 1 1 d . . . . . H38 H 0.906673 0.675489 0.361565 0.044 Uiso 1 1 calc R . . . . C39 C 0.9142(2) 0.5446(2) 0.40612(17) 0.0293(7) Uani 1 1 d . . . . . C41 C 0.4126(3) 0.4530(3) 0.2790(2) 0.0550(11) Uani 1 1 d . . . . . H41A H 0.430032 0.477551 0.230754 0.066 Uiso 1 1 calc R . . . . H41B H 0.340789 0.461435 0.285995 0.066 Uiso 1 1 calc R . . . . C42 C 0.4413(4) 0.3521(3) 0.2858(3) 0.0822(15) Uani 1 1 d . . . . . H42A H 0.396715 0.319913 0.319296 0.099 Uiso 1 1 calc R . . . . H42B H 0.437350 0.321726 0.237611 0.099 Uiso 1 1 calc R . . . . C43 C 0.5457(3) 0.3512(3) 0.3155(3) 0.0705(13) Uani 1 1 d . . . . . H43A H 0.593585 0.361905 0.276417 0.085 Uiso 1 1 calc R . . . . H43B H 0.561380 0.292444 0.339852 0.085 Uiso 1 1 calc R . . . . C44 C 0.5465(3) 0.4312(3) 0.3708(2) 0.0567(11) Uani 1 1 d . . . . . H44A H 0.526156 0.409839 0.419434 0.068 Uiso 1 1 calc R . . . . H44B H 0.613219 0.458699 0.375414 0.068 Uiso 1 1 calc R . . . . C51 C 0.3030(3) 0.7949(3) 0.2888(2) 0.0485(10) Uani 1 1 d . . . . . C52 C 0.3035(3) 0.6962(3) 0.2738(2) 0.0495(10) Uani 1 1 d . . . . . H52A H 0.303290 0.662442 0.319854 0.074 Uiso 1 1 calc GR . . . . H52B H 0.363021 0.680469 0.247016 0.074 Uiso 1 1 calc GR . . . . H52C H 0.244653 0.680013 0.244443 0.074 Uiso 1 1 calc GR . . . . C110 C 0.8329(2) 0.8095(3) 0.56871(19) 0.0365(8) Uani 1 1 d . . . . . C210 C 0.6140(2) 0.6903(2) 0.33735(19) 0.0310(8) Uani 1 1 d . . . . . C310 C 0.7138(2) 0.4994(3) 0.54113(19) 0.0346(8) Uani 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 0.02597(19) 0.0335(2) 0.0392(2) -0.0005(2) -0.00113(15) -0.00080(17) O11 0.0276(11) 0.0407(15) 0.0417(14) 0.0035(13) -0.0080(10) -0.0001(10) O12 0.0347(12) 0.074(2) 0.0541(17) -0.0149(15) -0.0114(12) -0.0141(13) O21 0.0349(12) 0.0293(13) 0.0388(14) 0.0007(11) -0.0059(10) -0.0029(10) O22 0.0334(11) 0.0400(15) 0.0387(14) -0.0040(12) -0.0068(10) -0.0073(10) O31 0.0356(12) 0.0350(15) 0.0406(15) 0.0047(12) 0.0066(10) 0.0038(11) O32 0.0471(14) 0.0360(15) 0.0540(17) 0.0062(13) 0.0175(12) -0.0015(12) N1 0.0320(13) 0.0314(16) 0.0284(15) 0.0034(13) 0.0005(11) -0.0034(12) N2 0.0245(12) 0.0334(16) 0.0296(15) -0.0006(13) 0.0009(11) -0.0022(11) N3 0.0234(12) 0.0333(16) 0.0300(15) -0.0008(13) -0.0041(11) 0.0007(11) N4 0.0362(14) 0.0375(18) 0.0461(19) -0.0087(15) 0.0085(13) -0.0082(13) N5 0.114(3) 0.050(3) 0.092(3) -0.002(2) -0.027(3) -0.008(2) C11 0.0336(16) 0.032(2) 0.0301(18) 0.0000(16) -0.0042(14) -0.0073(14) C12 0.046(2) 0.037(2) 0.041(2) 0.0002(19) -0.0074(17) -0.0111(17) C13 0.053(2) 0.036(2) 0.052(2) -0.0061(19) -0.0009(18) 0.0025(18) C14 0.0393(18) 0.038(2) 0.035(2) 0.0014(18) 0.0003(15) 0.0031(16) C15 0.044(2) 0.051(3) 0.059(3) -0.008(2) 0.0040(19) 0.0133(19) C16 0.0298(18) 0.068(3) 0.063(3) -0.003(2) 0.0003(18) 0.0092(19) C17 0.0305(17) 0.053(2) 0.047(2) -0.005(2) 0.0009(16) -0.0021(17) C18 0.0319(16) 0.039(2) 0.039(2) -0.0033(18) 0.0044(15) -0.0032(15) C19 0.0284(15) 0.035(2) 0.0262(17) 0.0039(16) 0.0018(13) 0.0002(14) C21 0.0240(14) 0.0338(19) 0.0289(18) -0.0029(16) 0.0035(13) 0.0007(14) C22 0.0327(17) 0.040(2) 0.043(2) 0.0052(18) -0.0082(15) -0.0032(16) C23 0.0359(17) 0.040(2) 0.046(2) 0.0131(19) -0.0092(16) -0.0020(16) C24 0.0301(16) 0.038(2) 0.039(2) 0.0004(17) 0.0041(15) -0.0042(15) C25 0.0426(19) 0.039(2) 0.053(2) 0.011(2) 0.0016(18) -0.0079(17) C26 0.045(2) 0.048(2) 0.047(2) 0.002(2) 0.0049(18) -0.0211(18) C27 0.0395(19) 0.062(3) 0.042(2) 0.005(2) -0.0062(17) -0.0198(19) C28 0.0310(17) 0.053(2) 0.035(2) 0.0077(18) -0.0018(15) -0.0113(17) C29 0.0260(15) 0.038(2) 0.0304(18) -0.0039(17) 0.0058(13) -0.0038(14) C31 0.0249(14) 0.036(2) 0.0295(18) -0.0012(17) -0.0056(13) -0.0025(14) C32 0.0285(16) 0.034(2) 0.042(2) 0.0037(17) -0.0010(15) -0.0037(15) C33 0.0280(16) 0.032(2) 0.038(2) -0.0009(17) -0.0070(14) 0.0010(14) C34 0.0221(14) 0.037(2) 0.0320(19) -0.0056(17) -0.0060(13) 0.0000(14) C35 0.0262(15) 0.041(2) 0.039(2) -0.0044(18) -0.0028(14) 0.0026(15) C36 0.0300(16) 0.048(2) 0.042(2) -0.007(2) 0.0024(15) -0.0033(16) C37 0.0422(19) 0.043(2) 0.043(2) 0.0039(19) 0.0061(17) -0.0074(17) C38 0.0332(17) 0.035(2) 0.042(2) 0.0011(18) 0.0020(15) 0.0021(15) C39 0.0230(14) 0.034(2) 0.0311(18) -0.0025(16) -0.0029(13) -0.0027(14) C41 0.060(2) 0.047(3) 0.058(3) -0.017(2) 0.001(2) -0.009(2) C42 0.089(4) 0.054(3) 0.104(4) -0.028(3) -0.006(3) 0.001(3) C43 0.078(3) 0.052(3) 0.082(4) 0.000(3) 0.026(3) 0.012(2) C44 0.053(2) 0.041(2) 0.076(3) 0.013(2) 0.000(2) -0.0047(19) C51 0.049(2) 0.045(3) 0.051(3) 0.006(2) -0.0133(18) -0.0067(19) C52 0.045(2) 0.043(3) 0.060(3) 0.004(2) 0.0019(18) 0.0017(18) C110 0.0340(17) 0.041(2) 0.0337(19) 0.0104(18) -0.0052(15) -0.0069(16) C210 0.0246(15) 0.034(2) 0.0340(19) -0.0037(17) 0.0036(14) 0.0035(14) C310 0.0304(16) 0.037(2) 0.036(2) -0.0043(18) -0.0028(15) -0.0011(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' 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 163.11(9) . . ? O11 Zn1 O31 104.37(9) . . ? O11 Zn1 N1 79.43(9) . . ? O11 Zn1 N2 91.92(9) . . ? O11 Zn1 N3 90.21(9) . . ? O21 Zn1 O31 91.97(9) . . ? O21 Zn1 N1 105.06(9) . . ? O21 Zn1 N2 72.82(9) . . ? O21 Zn1 N3 89.15(9) . . ? O31 Zn1 N1 90.46(9) . . ? O31 Zn1 N2 160.93(8) . . ? O31 Zn1 N3 77.68(9) . . ? N1 Zn1 N2 82.75(9) . . ? N1 Zn1 N3 161.90(10) . . ? N3 Zn1 N2 112.65(9) . . ? C110 O11 Zn1 118.01(19) . . ? C210 O21 Zn1 123.7(2) . . ? C310 O31 Zn1 117.7(2) . . ? C11 N1 Zn1 110.0(2) . . ? C11 N1 C19 118.5(3) . . ? C19 N1 Zn1 131.5(2) . . ? C21 N2 Zn1 105.10(19) . . ? C21 N2 C29 117.2(3) . . ? C29 N2 Zn1 134.3(2) . . ? C31 N3 Zn1 111.49(19) . . ? C31 N3 C39 117.8(3) . . ? C39 N3 Zn1 130.7(2) . . ? H4A N4 H4B 108.4 . . ? C41 N4 H4A 110.0 . . ? C41 N4 H4B 110.0 . . ? C44 N4 H4A 110.0 . . ? C44 N4 H4B 110.0 . . ? C44 N4 C41 108.4(3) . . ? N1 C11 C12 123.6(3) . . ? N1 C11 C110 116.2(3) . . ? C12 C11 C110 120.1(3) . . ? C11 C12 H12 120.4 . . ? C13 C12 C11 119.1(3) . . ? C13 C12 H12 120.4 . . ? C12 C13 H13 120.2 . . ? C12 C13 C14 119.5(3) . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 122.5(3) . . ? C13 C14 C19 118.4(3) . . ? C19 C14 C15 119.1(3) . . ? C14 C15 H15 120.1 . . ? C16 C15 C14 119.7(4) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 119.5 . . ? C15 C16 C17 121.0(3) . . ? C17 C16 H16 119.5 . . ? C16 C17 H17 119.7 . . ? C18 C17 C16 120.5(3) . . ? C18 C17 H17 119.7 . . ? C17 C18 H18 120.0 . . ? C17 C18 C19 120.0(3) . . ? C19 C18 H18 120.0 . . ? N1 C19 C14 120.8(3) . . ? N1 C19 C18 119.6(3) . . ? C18 C19 C14 119.6(3) . . ? N2 C21 C22 124.3(3) . . ? N2 C21 C210 116.0(3) . . ? C22 C21 C210 119.7(3) . . ? C21 C22 H22 120.5 . . ? C23 C22 C21 119.0(3) . . ? C23 C22 H22 120.5 . . ? C22 C23 H23 120.3 . . ? C22 C23 C24 119.4(3) . . ? C24 C23 H23 120.3 . . ? C23 C24 C25 122.4(3) . . ? C29 C24 C23 118.3(3) . . ? C29 C24 C25 119.3(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 C24 120.6(4) . . ? C26 C25 H25 119.7 . . ? C25 C26 H26 120.2 . . ? C25 C26 C27 119.6(3) . . ? C27 C26 H26 120.2 . . ? C26 C27 H27 119.3 . . ? C28 C27 C26 121.5(3) . . ? C28 C27 H27 119.3 . . ? C27 C28 H28 120.1 . . ? C27 C28 C29 119.9(3) . . ? C29 C28 H28 120.1 . . ? N2 C29 C24 121.7(3) . . ? N2 C29 C28 119.1(3) . . ? C24 C29 C28 119.2(3) . . ? N3 C31 C32 123.5(3) . . ? N3 C31 C310 115.6(3) . . ? C32 C31 C310 121.0(3) . . ? C31 C32 H32 120.3 . . ? C33 C32 C31 119.4(3) . . ? C33 C32 H32 120.3 . . ? C32 C33 H33 120.5 . . ? C32 C33 C34 119.0(3) . . ? C34 C33 H33 120.5 . . ? C33 C34 C35 122.3(3) . . ? C33 C34 C39 118.8(3) . . ? C39 C34 C35 118.9(3) . . ? C34 C35 H35 120.1 . . ? C36 C35 C34 119.8(3) . . ? C36 C35 H35 120.1 . . ? C35 C36 H36 119.6 . . ? C35 C36 C37 120.8(3) . . ? C37 C36 H36 119.6 . . ? C36 C37 H37 119.5 . . ? C38 C37 C36 121.0(3) . . ? C38 C37 H37 119.5 . . ? C37 C38 H38 120.2 . . ? C37 C38 C39 119.6(3) . . ? C39 C38 H38 120.2 . . ? N3 C39 C34 121.5(3) . . ? N3 C39 C38 118.6(3) . . ? C34 C39 C38 119.9(3) . . ? N4 C41 H41A 110.9 . . ? N4 C41 H41B 110.9 . . ? N4 C41 C42 104.1(3) . . ? H41A C41 H41B 109.0 . . ? C42 C41 H41A 110.9 . . ? C42 C41 H41B 110.9 . . ? C41 C42 H42A 110.6 . . ? C41 C42 H42B 110.6 . . ? H42A C42 H42B 108.7 . . ? C43 C42 C41 105.8(4) . . ? C43 C42 H42A 110.6 . . ? C43 C42 H42B 110.6 . . ? C42 C43 H43A 111.2 . . ? C42 C43 H43B 111.2 . . ? C42 C43 C44 102.9(3) . . ? H43A C43 H43B 109.1 . . ? C44 C43 H43A 111.2 . . ? C44 C43 H43B 111.2 . . ? N4 C44 C43 104.8(3) . . ? N4 C44 H44A 110.8 . . ? N4 C44 H44B 110.8 . . ? C43 C44 H44A 110.8 . . ? C43 C44 H44B 110.8 . . ? H44A C44 H44B 108.9 . . ? N5 C51 C52 178.9(5) . . ? C51 C52 H52A 109.5 . . ? C51 C52 H52B 109.5 . . ? C51 C52 H52C 109.5 . . ? H52A C52 H52B 109.5 . . ? H52A C52 H52C 109.5 . . ? H52B C52 H52C 109.5 . . ? O11 C110 C11 116.1(3) . . ? O12 C110 O11 126.5(3) . . ? O12 C110 C11 117.4(3) . . ? O21 C210 C21 118.0(3) . . ? O22 C210 O21 124.4(3) . . ? O22 C210 C21 117.6(3) . . ? O31 C310 C31 117.0(3) . . ? O32 C310 O31 126.4(3) . . ? O32 C310 C31 116.7(3) . . ? 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 1.996(2) . ? Zn1 O21 2.007(2) . ? Zn1 O31 2.065(2) . ? Zn1 N1 2.186(3) . ? Zn1 N2 2.495(3) . ? Zn1 N3 2.198(3) . ? O11 C110 1.275(4) . ? O12 C110 1.220(4) . ? O21 C210 1.267(4) . ? O22 C210 1.240(4) . ? O31 C310 1.252(4) . ? O32 C310 1.245(4) . ? N1 C11 1.316(4) . ? N1 C19 1.386(4) . ? N2 C21 1.332(4) . ? N2 C29 1.377(4) . ? N3 C31 1.325(4) . ? N3 C39 1.378(4) . ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? N4 C41 1.490(4) . ? N4 C44 1.488(4) . ? N5 C51 1.131(5) . ? C11 C12 1.396(5) . ? C11 C110 1.532(4) . ? C12 H12 0.9300 . ? C12 C13 1.362(4) . ? C13 H13 0.9300 . ? C13 C14 1.408(5) . ? C14 C15 1.419(4) . ? C14 C19 1.409(5) . ? C15 H15 0.9300 . ? C15 C16 1.362(5) . ? C16 H16 0.9300 . ? C16 C17 1.398(5) . ? C17 H17 0.9300 . ? C17 C18 1.367(4) . ? C18 H18 0.9300 . ? C18 C19 1.406(4) . ? C21 C22 1.394(4) . ? C21 C210 1.512(4) . ? C22 H22 0.9300 . ? C22 C23 1.357(5) . ? C23 H23 0.9300 . ? C23 C24 1.413(4) . ? C24 C25 1.417(5) . ? C24 C29 1.409(5) . ? C25 H25 0.9300 . ? C25 C26 1.365(5) . ? C26 H26 0.9300 . ? C26 C27 1.405(5) . ? C27 H27 0.9300 . ? C27 C28 1.364(5) . ? C28 H28 0.9300 . ? C28 C29 1.412(4) . ? C31 C32 1.403(4) . ? C31 C310 1.531(4) . ? C32 H32 0.9300 . ? C32 C33 1.360(4) . ? C33 H33 0.9300 . ? C33 C34 1.404(5) . ? C34 C35 1.429(4) . ? C34 C39 1.407(4) . ? C35 H35 0.9300 . ? C35 C36 1.359(5) . ? C36 H36 0.9300 . ? C36 C37 1.399(5) . ? C37 H37 0.9300 . ? C37 C38 1.368(4) . ? C38 H38 0.9300 . ? C38 C39 1.409(5) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C41 C42 1.500(6) . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C42 C43 1.470(6) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C43 C44 1.518(6) . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C51 C52 1.440(5) . ? C52 H52A 0.9600 . ? C52 H52B 0.9600 . ? C52 H52C 0.9600 . ? 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 N4 H4A O22 0.89 1.90 2.776(4) 165.9 . yes N4 H4B O32 0.89 1.91 2.772(3) 163.7 3_666 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 179.3(3) . . . . ? Zn1 O11 C110 C11 0.3(4) . . . . ? Zn1 O21 C210 O22 -170.2(2) . . . . ? Zn1 O21 C210 C21 9.9(4) . . . . ? Zn1 O31 C310 O32 -170.1(3) . . . . ? Zn1 O31 C310 C31 8.8(4) . . . . ? Zn1 N1 C11 C12 174.3(3) . . . . ? Zn1 N1 C11 C110 -5.5(3) . . . . ? Zn1 N1 C19 C14 -174.4(2) . . . . ? Zn1 N1 C19 C18 6.5(4) . . . . ? Zn1 N2 C21 C22 161.2(3) . . . . ? Zn1 N2 C21 C210 -18.8(3) . . . . ? Zn1 N2 C29 C24 -153.1(2) . . . . ? Zn1 N2 C29 C28 27.5(4) . . . . ? Zn1 N3 C31 C32 -177.8(2) . . . . ? Zn1 N3 C31 C310 1.6(3) . . . . ? Zn1 N3 C39 C34 176.2(2) . . . . ? Zn1 N3 C39 C38 -4.7(4) . . . . ? N1 C11 C12 C13 1.3(5) . . . . ? N1 C11 C110 O11 3.9(4) . . . . ? N1 C11 C110 O12 -175.1(3) . . . . ? N2 C21 C22 C23 -1.4(5) . . . . ? N2 C21 C210 O21 9.9(4) . . . . ? N2 C21 C210 O22 -170.1(3) . . . . ? N3 C31 C32 C33 1.0(5) . . . . ? N3 C31 C310 O31 -6.9(4) . . . . ? N3 C31 C310 O32 172.1(3) . . . . ? N4 C41 C42 C43 -30.0(5) . . . . ? C11 N1 C19 C14 1.8(4) . . . . ? C11 N1 C19 C18 -177.4(3) . . . . ? C11 C12 C13 C14 0.8(5) . . . . ? C12 C11 C110 O11 -176.0(3) . . . . ? C12 C11 C110 O12 5.0(5) . . . . ? C12 C13 C14 C15 179.3(3) . . . . ? C12 C13 C14 C19 -1.5(5) . . . . ? C13 C14 C15 C16 -179.9(4) . . . . ? C13 C14 C19 N1 0.2(5) . . . . ? C13 C14 C19 C18 179.4(3) . . . . ? C14 C15 C16 C17 0.0(6) . . . . ? C15 C14 C19 N1 179.5(3) . . . . ? C15 C14 C19 C18 -1.4(5) . . . . ? C15 C16 C17 C18 -0.4(6) . . . . ? C16 C17 C18 C19 -0.1(5) . . . . ? C17 C18 C19 N1 -179.9(3) . . . . ? C17 C18 C19 C14 1.0(5) . . . . ? C19 N1 C11 C12 -2.6(5) . . . . ? C19 N1 C11 C110 177.5(3) . . . . ? C19 C14 C15 C16 0.9(5) . . . . ? C21 N2 C29 C24 2.5(4) . . . . ? C21 N2 C29 C28 -176.8(3) . . . . ? C21 C22 C23 C24 2.2(5) . . . . ? C22 C21 C210 O21 -170.1(3) . . . . ? C22 C21 C210 O22 9.9(4) . . . . ? C22 C23 C24 C25 178.6(3) . . . . ? C22 C23 C24 C29 -0.7(5) . . . . ? C23 C24 C25 C26 -178.3(3) . . . . ? C23 C24 C29 N2 -1.7(5) . . . . ? C23 C24 C29 C28 177.6(3) . . . . ? C24 C25 C26 C27 0.4(5) . . . . ? C25 C24 C29 N2 179.0(3) . . . . ? C25 C24 C29 C28 -1.7(5) . . . . ? C25 C26 C27 C28 -1.0(6) . . . . ? C26 C27 C28 C29 0.2(5) . . . . ? C27 C28 C29 N2 -179.5(3) . . . . ? C27 C28 C29 C24 1.2(5) . . . . ? C29 N2 C21 C22 -1.0(4) . . . . ? C29 N2 C21 C210 179.0(3) . . . . ? C29 C24 C25 C26 0.9(5) . . . . ? C31 N3 C39 C34 -1.4(4) . . . . ? C31 N3 C39 C38 177.7(3) . . . . ? C31 C32 C33 C34 -1.2(5) . . . . ? C32 C31 C310 O31 172.5(3) . . . . ? C32 C31 C310 O32 -8.5(5) . . . . ? C32 C33 C34 C35 -178.6(3) . . . . ? C32 C33 C34 C39 0.1(4) . . . . ? C33 C34 C35 C36 178.2(3) . . . . ? C33 C34 C39 N3 1.2(4) . . . . ? C33 C34 C39 C38 -177.8(3) . . . . ? C34 C35 C36 C37 -0.1(5) . . . . ? C35 C34 C39 N3 -180.0(3) . . . . ? C35 C34 C39 C38 0.9(4) . . . . ? C35 C36 C37 C38 0.4(5) . . . . ? C36 C37 C38 C39 0.0(5) . . . . ? C37 C38 C39 N3 -179.8(3) . . . . ? C37 C38 C39 C34 -0.7(5) . . . . ? C39 N3 C31 C32 0.3(4) . . . . ? C39 N3 C31 C310 179.7(3) . . . . ? C39 C34 C35 C36 -0.5(5) . . . . ? C41 N4 C44 C43 13.1(4) . . . . ? C41 C42 C43 C44 38.1(5) . . . . ? C42 C43 C44 N4 -31.3(4) . . . . ? C44 N4 C41 C42 9.8(4) . . . . ? C110 C11 C12 C13 -178.8(3) . . . . ? C210 C21 C22 C23 178.7(3) . . . . ? C310 C31 C32 C33 -178.4(3) . . . . ?