#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:42:26 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258103 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240519.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_7240519 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, C2 H3 N' _chemical_formula_sum 'C29 H29 N5 O4 Zn' _chemical_formula_weight 576.94 _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 110.850(3) _cell_angle_beta 101.862(2) _cell_angle_gamma 101.479(2) _cell_formula_units_Z 2 _cell_length_a 7.6353(2) _cell_length_b 15.1456(4) _cell_length_c 15.5015(4) _cell_measurement_reflns_used 12031 _cell_measurement_temperature 125.00(10) _cell_measurement_theta_max 30.1070 _cell_measurement_theta_min 3.1970 _cell_volume 1565.17(9) _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 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 -37.00 56.00 1.00 5.50 -- -14.36 37.00-180.00 93 2 \w -74.00 -48.00 1.00 5.50 -- -14.36 128.00 147.50 26 3 \w -16.00 92.00 1.00 5.50 -- 14.52 77.00 60.00 108 4 \w 35.00 103.00 1.00 5.50 -- 14.52 178.00 -30.00 68 5 \w 6.00 91.00 1.00 5.50 -- 14.52 37.00-150.00 85 6 \w -15.00 86.00 1.00 5.50 -- 14.52 57.00 -60.00 101 7 \w -54.00 44.00 1.00 5.50 -- 14.52 -57.00 -60.00 98 8 \w 17.00 92.00 1.00 5.50 -- 14.52-154.00 128.96 75 ; _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 0.0738943000 _diffrn_orient_matrix_UB_12 -0.0204074000 _diffrn_orient_matrix_UB_13 -0.0087097000 _diffrn_orient_matrix_UB_21 -0.0620004000 _diffrn_orient_matrix_UB_22 -0.0482811000 _diffrn_orient_matrix_UB_23 -0.0166397000 _diffrn_orient_matrix_UB_31 -0.0241223000 _diffrn_orient_matrix_UB_32 -0.0028107000 _diffrn_orient_matrix_UB_33 -0.0478007000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_unetI/netI 0.0283 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 26129 _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 27.498 _diffrn_reflns_theta_min 2.507 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.823 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90914 _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 yellow _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.333 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 358 _refine_ls_number_reflns 7177 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0321 _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^)+(0.0414P)^2^+0.6084P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0862 _refine_ls_wR_factor_ref 0.0883 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6496 _reflns_number_total 7177 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03192e3.cif _cod_data_source_block 4a _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_original_cell_volume 1565.17(8) _cod_database_code 7240519 _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 0.853 _shelx_estimated_absorpt_t_min 0.734 _shelx_res_file ; TITL mob535_a.res in P-1 mob535.res created by SHELXL-2018/3 at 11:12:56 on 16-Dec-2019 CELL 0.71073 7.6353 15.1456 15.5015 110.85 101.862 101.479 ZERR 2 0.0002 0.0004 0.0004 0.003 0.002 0.002 LATT 1 SFAC C H N O Zn UNIT 58 58 10 8 2 EQIV $1 1+X,+Y,+Z L.S. 10 PLAN 10 SIZE 0.4 0.3 0.2 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 MORE -1 BOND $H htab CONF LIST 6 fmap 2 acta MERG 2 SHEL 30 0.7696 OMIT 0 -2 1 OMIT -1 1 1 OMIT 0 -1 2 OMIT -1 2 0 REM REM REM WGHT 0.041400 0.608400 FVAR 57.66915 ZN1 5 0.514286 0.690692 0.357154 11.00000 0.01578 0.02643 = 0.02723 0.01403 0.00819 0.00784 O11 4 0.249361 0.634624 0.353241 11.00000 0.01726 0.03311 = 0.03928 0.02168 0.01121 0.00899 O12 4 -0.020561 0.667327 0.361075 11.00000 0.01946 0.04651 = 0.04939 0.02808 0.01702 0.01313 O21 4 0.715458 0.789288 0.478122 11.00000 0.02145 0.02391 = 0.03265 0.01100 0.00619 0.00673 O22 4 0.923248 0.805850 0.611527 11.00000 0.03096 0.03324 = 0.03490 0.01177 -0.00392 -0.00433 N1 3 0.393988 0.809387 0.354494 11.00000 0.01859 0.02903 = 0.02409 0.01332 0.00781 0.01002 N2 3 0.610672 0.592977 0.414332 11.00000 0.01509 0.02510 = 0.02382 0.01163 0.00893 0.00672 N31 3 0.632326 0.630952 0.088331 11.00000 0.03249 0.10711 = 0.02484 0.01982 0.01155 0.02438 N32 3 0.608659 0.655463 0.242802 11.00000 0.01843 0.03273 = 0.02918 0.01412 0.00957 0.00958 C11 1 0.230813 0.794719 0.371496 11.00000 0.01751 0.03461 = 0.02165 0.01413 0.00535 0.00999 C12 1 0.140269 0.868553 0.396550 11.00000 0.01976 0.03844 = 0.02785 0.01411 0.00920 0.01379 AFIX 43 H12 2 0.026663 0.855545 0.409619 11.00000 -1.20000 AFIX 0 C13 1 0.222728 0.959579 0.401248 11.00000 0.02457 0.03434 = 0.02840 0.01201 0.00814 0.01740 AFIX 43 H13 2 0.166249 1.009627 0.418367 11.00000 -1.20000 AFIX 0 C14 1 0.394337 0.977318 0.379957 11.00000 0.02337 0.02855 = 0.02222 0.00913 0.00425 0.01144 C15 1 0.487022 1.068941 0.381231 11.00000 0.02981 0.02655 = 0.03438 0.01147 0.00679 0.01296 AFIX 43 H15 2 0.433402 1.120379 0.395404 11.00000 -1.20000 AFIX 0 C16 1 0.654158 1.082151 0.361829 11.00000 0.03284 0.02568 = 0.03956 0.01488 0.00839 0.00700 AFIX 43 H16 2 0.714091 1.142690 0.363263 11.00000 -1.20000 AFIX 0 C17 1 0.737158 1.004556 0.339537 11.00000 0.02406 0.03095 = 0.03898 0.01585 0.01147 0.00781 AFIX 43 H17 2 0.851134 1.014478 0.326331 11.00000 -1.20000 AFIX 0 C18 1 0.651329 0.915031 0.337220 11.00000 0.02264 0.02764 = 0.03304 0.01330 0.00984 0.01049 AFIX 43 H18 2 0.706947 0.864416 0.322547 11.00000 -1.20000 AFIX 0 C19 1 0.478458 0.899586 0.357102 11.00000 0.02106 0.02618 = 0.02322 0.01161 0.00638 0.00991 C21 1 0.748632 0.643699 0.496067 11.00000 0.01445 0.02795 = 0.02473 0.01222 0.00858 0.00529 C22 1 0.840726 0.598602 0.548805 11.00000 0.01785 0.03640 = 0.02695 0.01665 0.00584 0.00680 AFIX 43 H22 2 0.936869 0.636919 0.606398 11.00000 -1.20000 AFIX 0 C23 1 0.787029 0.498103 0.514290 11.00000 0.02424 0.03862 = 0.03462 0.02480 0.01360 0.01465 AFIX 43 H23 2 0.845293 0.467087 0.548584 11.00000 -1.20000 AFIX 0 C24 1 0.642511 0.441315 0.426213 11.00000 0.02547 0.03022 = 0.03019 0.01725 0.01680 0.01158 C25 1 0.579900 0.336486 0.384751 11.00000 0.04436 0.03005 = 0.04182 0.02213 0.02305 0.01649 AFIX 43 H25 2 0.635490 0.302376 0.416128 11.00000 -1.20000 AFIX 0 C26 1 0.439755 0.285161 0.299781 11.00000 0.05505 0.02378 = 0.03846 0.01114 0.02241 0.00891 AFIX 43 H26 2 0.401141 0.216350 0.273149 11.00000 -1.20000 AFIX 0 C27 1 0.352369 0.335769 0.251663 11.00000 0.03664 0.03240 = 0.02774 0.00822 0.01174 0.00283 AFIX 43 H27 2 0.255765 0.299989 0.193816 11.00000 -1.20000 AFIX 0 C28 1 0.408735 0.437272 0.289506 11.00000 0.02450 0.03010 = 0.02673 0.01222 0.00986 0.00678 AFIX 43 H28 2 0.350513 0.470026 0.257349 11.00000 -1.20000 AFIX 0 C29 1 0.555010 0.491785 0.377187 11.00000 0.01937 0.02550 = 0.02571 0.01295 0.01274 0.00794 C31 1 0.837825 0.656489 0.117427 11.00000 0.03367 0.08517 = 0.03367 0.02643 0.01944 0.02772 AFIX 23 H31A 2 0.876705 0.612643 0.067192 11.00000 -1.20000 H31B 2 0.882468 0.648011 0.176387 11.00000 -1.20000 AFIX 0 C32 1 0.921032 0.761386 0.133884 11.00000 0.05414 0.08608 = 0.04083 0.02554 0.02213 0.02624 AFIX 23 H32A 2 1.056426 0.776874 0.150640 11.00000 -1.20000 H32B 2 0.890340 0.805345 0.187684 11.00000 -1.20000 AFIX 0 C33 1 0.846809 0.778291 0.043295 11.00000 0.10196 0.11940 = 0.06597 0.05989 0.04786 0.05982 AFIX 23 H33A 2 0.890104 0.848222 0.057989 11.00000 -1.20000 H33B 2 0.895085 0.742818 -0.007471 11.00000 -1.20000 AFIX 0 C34 1 0.632755 0.742461 0.008102 11.00000 0.10708 0.21014 = 0.06092 0.08654 0.05164 0.10996 AFIX 23 H34A 2 0.584733 0.785681 0.054030 11.00000 -1.20000 H34B 2 0.588579 0.745698 -0.053691 11.00000 -1.20000 AFIX 0 C35 1 0.560694 0.639996 -0.002713 11.00000 0.04749 0.19736 = 0.02885 0.04380 0.01459 0.04880 AFIX 23 H35A 2 0.424799 0.620452 -0.021899 11.00000 -1.20000 H35B 2 0.598322 0.595796 -0.053290 11.00000 -1.20000 AFIX 0 C36 1 0.537572 0.641321 0.154291 11.00000 0.02515 0.05407 = 0.02685 0.01044 0.00832 0.01157 C37 1 0.332810 0.633822 0.121472 11.00000 0.02446 0.11532 = 0.03091 0.02113 0.00474 0.01742 AFIX 137 H37A 2 0.278328 0.633942 0.172068 11.00000 -1.50000 H37B 2 0.269050 0.573518 0.064615 11.00000 -1.50000 H37C 2 0.320789 0.689235 0.106856 11.00000 -1.50000 AFIX 0 C210 1 0.803190 0.755802 0.532479 11.00000 0.01771 0.02822 = 0.03030 0.01225 0.00862 0.00415 C110 1 0.144414 0.691079 0.361805 11.00000 0.01919 0.03513 = 0.02602 0.01782 0.00867 0.00987 C41 1 0.067305 0.575049 0.842910 11.00000 0.03155 0.07361 = 0.03219 0.02032 0.00740 0.02134 C42 1 0.147445 0.572225 0.765520 11.00000 0.04534 0.06845 = 0.03402 0.01633 0.01348 0.00245 AFIX 137 H42A 2 0.096705 0.507360 0.713505 11.00000 -1.50000 H42B 2 0.281084 0.587365 0.789257 11.00000 -1.50000 H42C 2 0.117748 0.620076 0.742422 11.00000 -1.50000 AFIX 0 N4 3 0.003893 0.576431 0.902732 11.00000 0.05798 0.13992 = 0.04862 0.03932 0.02647 0.03710 H32 2 0.719794 0.659990 0.258635 11.00000 0.03241 HKLF 4 REM mob535_a.res in P-1 REM wR2 = 0.0883, GooF = S = 1.089, Restrained GooF = 1.089 for all data REM R1 = 0.0321 for 6496 Fo > 4sig(Fo) and 0.0360 for all 7177 data REM 358 parameters refined using 0 restraints END WGHT 0.0414 0.6084 REM Instructions for potential hydrogen bonds EQIV $2 -x, -y+1, -z+1 HTAB C42 O12_$2 HTAB N32 O12_$1 REM Highest difference peak 0.333, deepest hole -0.321, 1-sigma level 0.055 Q1 1 0.6053 0.4626 0.4013 11.00000 0.05 0.33 Q2 1 0.1996 0.7457 0.3685 11.00000 0.05 0.33 Q3 1 0.4208 0.9323 0.3508 11.00000 0.05 0.29 Q4 1 0.7931 0.6997 0.5111 11.00000 0.05 0.28 Q5 1 0.6186 0.3942 0.4019 11.00000 0.05 0.28 Q6 1 0.7068 0.4681 0.4674 11.00000 0.05 0.27 Q7 1 0.6007 0.6595 0.3958 11.00000 0.05 0.26 Q8 1 0.4414 0.6324 0.1369 11.00000 0.05 0.26 Q9 1 0.1688 0.8188 0.3603 11.00000 0.05 0.26 Q10 1 0.5783 0.9126 0.3616 11.00000 0.05 0.26 ; _shelx_res_checksum 99487 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 0.51429(2) 0.69069(2) 0.35715(2) 0.02174(7) Uani 1 1 d . . . . . O11 O 0.24936(15) 0.63462(9) 0.35324(9) 0.0272(3) Uani 1 1 d . . . . . O12 O -0.02056(17) 0.66733(11) 0.36107(10) 0.0344(3) Uani 1 1 d . . . . . O21 O 0.71546(16) 0.78929(9) 0.47812(9) 0.0265(3) Uani 1 1 d . . . . . O22 O 0.92325(18) 0.80585(10) 0.61153(10) 0.0382(3) Uani 1 1 d . . . . . N1 N 0.39399(18) 0.80939(11) 0.35449(10) 0.0225(3) Uani 1 1 d . . . . . N2 N 0.61067(17) 0.59298(10) 0.41433(10) 0.0203(3) Uani 1 1 d . . . . . N31 N 0.6323(2) 0.63095(19) 0.08833(12) 0.0560(6) Uani 1 1 d . . . . . N32 N 0.6087(2) 0.65546(11) 0.24280(11) 0.0257(3) Uani 1 1 d . . . . . C11 C 0.2308(2) 0.79472(13) 0.37150(12) 0.0236(3) Uani 1 1 d . . . . . C12 C 0.1403(2) 0.86855(14) 0.39655(12) 0.0274(4) Uani 1 1 d . . . . . H12 H 0.026663 0.855545 0.409619 0.033 Uiso 1 1 calc R . . . . C13 C 0.2227(2) 0.95958(14) 0.40125(13) 0.0280(4) Uani 1 1 d . . . . . H13 H 0.166249 1.009627 0.418367 0.034 Uiso 1 1 calc R . . . . C14 C 0.3943(2) 0.97732(13) 0.37996(12) 0.0250(3) Uani 1 1 d . . . . . C15 C 0.4870(2) 1.06894(14) 0.38123(13) 0.0303(4) Uani 1 1 d . . . . . H15 H 0.433402 1.120379 0.395404 0.036 Uiso 1 1 calc R . . . . C16 C 0.6542(3) 1.08215(14) 0.36183(14) 0.0330(4) Uani 1 1 d . . . . . H16 H 0.714091 1.142690 0.363263 0.040 Uiso 1 1 calc R . . . . C17 C 0.7372(2) 1.00456(14) 0.33954(14) 0.0307(4) Uani 1 1 d . . . . . H17 H 0.851134 1.014478 0.326331 0.037 Uiso 1 1 calc R . . . . C18 C 0.6513(2) 0.91503(13) 0.33722(13) 0.0268(3) Uani 1 1 d . . . . . H18 H 0.706947 0.864416 0.322547 0.032 Uiso 1 1 calc R . . . . C19 C 0.4785(2) 0.89959(13) 0.35710(12) 0.0227(3) Uani 1 1 d . . . . . C21 C 0.7486(2) 0.64370(12) 0.49607(12) 0.0217(3) Uani 1 1 d . . . . . C22 C 0.8407(2) 0.59860(14) 0.54880(13) 0.0264(3) Uani 1 1 d . . . . . H22 H 0.936869 0.636919 0.606398 0.032 Uiso 1 1 calc R . . . . C23 C 0.7870(2) 0.49810(14) 0.51429(13) 0.0280(4) Uani 1 1 d . . . . . H23 H 0.845293 0.467087 0.548584 0.034 Uiso 1 1 calc R . . . . C24 C 0.6425(2) 0.44132(13) 0.42621(12) 0.0253(3) Uani 1 1 d . . . . . C25 C 0.5799(3) 0.33649(14) 0.38475(15) 0.0341(4) Uani 1 1 d . . . . . H25 H 0.635490 0.302376 0.416128 0.041 Uiso 1 1 calc R . . . . C26 C 0.4398(3) 0.28516(15) 0.29978(15) 0.0387(4) Uani 1 1 d . . . . . H26 H 0.401141 0.216350 0.273149 0.046 Uiso 1 1 calc R . . . . C27 C 0.3524(3) 0.33577(15) 0.25166(14) 0.0344(4) Uani 1 1 d . . . . . H27 H 0.255765 0.299989 0.193816 0.041 Uiso 1 1 calc R . . . . C28 C 0.4087(2) 0.43727(13) 0.28951(12) 0.0268(3) Uani 1 1 d . . . . . H28 H 0.350513 0.470026 0.257349 0.032 Uiso 1 1 calc R . . . . C29 C 0.5550(2) 0.49179(12) 0.37719(12) 0.0216(3) Uani 1 1 d . . . . . C31 C 0.8378(3) 0.6565(2) 0.11743(16) 0.0472(6) Uani 1 1 d . . . . . H31A H 0.876705 0.612643 0.067192 0.057 Uiso 1 1 calc R . . . . H31B H 0.882468 0.648011 0.176387 0.057 Uiso 1 1 calc R . . . . C32 C 0.9210(4) 0.7614(2) 0.13388(18) 0.0584(7) Uani 1 1 d . . . . . H32A H 1.056426 0.776874 0.150640 0.070 Uiso 1 1 calc R . . . . H32B H 0.890340 0.805345 0.187684 0.070 Uiso 1 1 calc R . . . . C33 C 0.8468(5) 0.7783(3) 0.0433(2) 0.0814(10) Uani 1 1 d . . . . . H33A H 0.890104 0.848222 0.057989 0.098 Uiso 1 1 calc R . . . . H33B H 0.895085 0.742818 -0.007471 0.098 Uiso 1 1 calc R . . . . C34 C 0.6328(6) 0.7425(4) 0.0081(2) 0.1026(16) Uani 1 1 d . . . . . H34A H 0.584733 0.785681 0.054030 0.123 Uiso 1 1 calc R . . . . H34B H 0.588579 0.745698 -0.053691 0.123 Uiso 1 1 calc R . . . . C35 C 0.5607(4) 0.6400(4) -0.00271(18) 0.0897(14) Uani 1 1 d . . . . . H35A H 0.424799 0.620452 -0.021899 0.108 Uiso 1 1 calc R . . . . H35B H 0.598322 0.595796 -0.053290 0.108 Uiso 1 1 calc R . . . . C36 C 0.5376(3) 0.64132(17) 0.15429(14) 0.0372(4) Uani 1 1 d . . . . . C37 C 0.3328(3) 0.6338(2) 0.12147(16) 0.0607(8) Uani 1 1 d . . . . . H37A H 0.278328 0.633942 0.172068 0.091 Uiso 1 1 calc GR . . . . H37B H 0.269050 0.573518 0.064615 0.091 Uiso 1 1 calc GR . . . . H37C H 0.320789 0.689235 0.106856 0.091 Uiso 1 1 calc GR . . . . C210 C 0.8032(2) 0.75580(13) 0.53248(13) 0.0256(3) Uani 1 1 d . . . . . C110 C 0.1444(2) 0.69108(14) 0.36180(12) 0.0247(3) Uani 1 1 d . . . . . C41 C 0.0673(3) 0.5750(2) 0.84291(15) 0.0457(5) Uani 1 1 d . . . . . C42 C 0.1474(3) 0.5722(2) 0.76552(16) 0.0528(6) Uani 1 1 d . . . . . H42A H 0.096705 0.507360 0.713505 0.079 Uiso 1 1 calc GR . . . . H42B H 0.281084 0.587365 0.789257 0.079 Uiso 1 1 calc GR . . . . H42C H 0.117748 0.620076 0.742422 0.079 Uiso 1 1 calc GR . . . . N4 N 0.0039(3) 0.5764(2) 0.90273(17) 0.0792(8) Uani 1 1 d . . . . . H32 H 0.720(3) 0.6600(16) 0.2586(15) 0.032(6) 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 0.01578(10) 0.02643(11) 0.02723(11) 0.01403(9) 0.00819(7) 0.00784(7) O11 0.0173(5) 0.0331(7) 0.0393(7) 0.0217(6) 0.0112(5) 0.0090(5) O12 0.0195(6) 0.0465(8) 0.0494(8) 0.0281(7) 0.0170(6) 0.0131(5) O21 0.0214(6) 0.0239(6) 0.0327(7) 0.0110(5) 0.0062(5) 0.0067(5) O22 0.0310(7) 0.0332(8) 0.0349(7) 0.0118(6) -0.0039(6) -0.0043(6) N1 0.0186(6) 0.0290(8) 0.0241(7) 0.0133(6) 0.0078(5) 0.0100(5) N2 0.0151(6) 0.0251(7) 0.0238(7) 0.0116(6) 0.0089(5) 0.0067(5) N31 0.0325(9) 0.1071(19) 0.0248(9) 0.0198(10) 0.0116(7) 0.0244(10) N32 0.0184(7) 0.0327(8) 0.0292(8) 0.0141(7) 0.0096(6) 0.0096(6) C11 0.0175(7) 0.0346(9) 0.0216(8) 0.0141(7) 0.0053(6) 0.0100(7) C12 0.0198(8) 0.0384(10) 0.0278(9) 0.0141(8) 0.0092(6) 0.0138(7) C13 0.0246(8) 0.0343(10) 0.0284(9) 0.0120(8) 0.0081(7) 0.0174(7) C14 0.0234(8) 0.0285(9) 0.0222(8) 0.0091(7) 0.0043(6) 0.0114(7) C15 0.0298(9) 0.0265(9) 0.0344(10) 0.0115(8) 0.0068(7) 0.0130(7) C16 0.0328(9) 0.0257(9) 0.0396(10) 0.0149(8) 0.0084(8) 0.0070(7) C17 0.0241(8) 0.0309(10) 0.0390(10) 0.0159(8) 0.0115(7) 0.0078(7) C18 0.0226(8) 0.0276(9) 0.0330(9) 0.0133(8) 0.0098(7) 0.0105(7) C19 0.0211(7) 0.0262(8) 0.0232(8) 0.0116(7) 0.0064(6) 0.0099(6) C21 0.0144(7) 0.0279(9) 0.0247(8) 0.0122(7) 0.0086(6) 0.0053(6) C22 0.0178(7) 0.0364(10) 0.0269(8) 0.0167(8) 0.0058(6) 0.0068(7) C23 0.0242(8) 0.0386(10) 0.0346(9) 0.0248(8) 0.0136(7) 0.0147(7) C24 0.0255(8) 0.0302(9) 0.0302(9) 0.0173(8) 0.0168(7) 0.0116(7) C25 0.0444(11) 0.0301(10) 0.0418(11) 0.0221(9) 0.0231(9) 0.0165(8) C26 0.0550(12) 0.0238(9) 0.0385(11) 0.0111(8) 0.0224(9) 0.0089(9) C27 0.0366(10) 0.0324(10) 0.0277(9) 0.0082(8) 0.0117(8) 0.0028(8) C28 0.0245(8) 0.0301(9) 0.0267(9) 0.0122(7) 0.0099(7) 0.0068(7) C29 0.0194(7) 0.0255(8) 0.0257(8) 0.0129(7) 0.0127(6) 0.0079(6) C31 0.0337(10) 0.0852(18) 0.0337(11) 0.0264(12) 0.0194(9) 0.0277(11) C32 0.0541(14) 0.086(2) 0.0408(13) 0.0255(14) 0.0221(11) 0.0262(14) C33 0.102(2) 0.119(3) 0.0660(19) 0.060(2) 0.0479(18) 0.060(2) C34 0.107(3) 0.210(5) 0.061(2) 0.087(3) 0.052(2) 0.110(3) C35 0.0475(15) 0.197(4) 0.0289(13) 0.044(2) 0.0146(11) 0.049(2) C36 0.0252(9) 0.0541(13) 0.0269(9) 0.0104(9) 0.0083(7) 0.0116(8) C37 0.0245(10) 0.115(2) 0.0309(11) 0.0211(13) 0.0047(8) 0.0174(12) C210 0.0177(7) 0.0282(9) 0.0303(9) 0.0122(7) 0.0086(6) 0.0042(6) C110 0.0192(7) 0.0351(10) 0.0260(8) 0.0178(8) 0.0087(6) 0.0099(7) C41 0.0316(10) 0.0736(17) 0.0322(11) 0.0203(11) 0.0074(8) 0.0213(10) C42 0.0453(12) 0.0684(17) 0.0340(11) 0.0163(11) 0.0135(9) 0.0024(11) N4 0.0580(14) 0.140(3) 0.0486(13) 0.0393(16) 0.0265(11) 0.0371(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 N1 78.18(5) . . ? O11 Zn1 N2 91.90(5) . . ? O21 Zn1 O11 123.60(5) . . ? O21 Zn1 N1 88.57(5) . . ? O21 Zn1 N2 79.71(5) . . ? N2 Zn1 N1 157.06(5) . . ? N32 Zn1 O11 124.51(6) . . ? N32 Zn1 O21 111.89(6) . . ? N32 Zn1 N1 104.75(6) . . ? N32 Zn1 N2 97.93(5) . . ? C110 O11 Zn1 117.87(11) . . ? C210 O21 Zn1 117.38(11) . . ? C11 N1 Zn1 110.46(11) . . ? C11 N1 C19 119.06(14) . . ? C19 N1 Zn1 129.04(10) . . ? C21 N2 Zn1 110.66(11) . . ? C21 N2 C29 119.32(14) . . ? C29 N2 Zn1 129.97(11) . . ? C31 N31 C35 110.73(19) . . ? C36 N31 C31 121.41(17) . . ? C36 N31 C35 122.06(19) . . ? Zn1 N32 H32 111.1(15) . . ? C36 N32 Zn1 132.72(13) . . ? C36 N32 H32 115.3(15) . . ? N1 C11 C12 123.46(16) . . ? N1 C11 C110 115.01(14) . . ? C12 C11 C110 121.54(14) . . ? C11 C12 H12 120.7 . . ? C13 C12 C11 118.69(15) . . ? C13 C12 H12 120.7 . . ? C12 C13 H13 120.2 . . ? C12 C13 C14 119.67(15) . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 123.20(16) . . ? C13 C14 C19 118.19(16) . . ? C15 C14 C19 118.61(15) . . ? C14 C15 H15 119.8 . . ? C16 C15 C14 120.46(16) . . ? C16 C15 H15 119.8 . . ? C15 C16 H16 119.7 . . ? C15 C16 C17 120.54(17) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 119.7 . . ? C18 C17 C16 120.60(16) . . ? C18 C17 H17 119.7 . . ? C17 C18 H18 120.0 . . ? C17 C18 C19 119.92(16) . . ? C19 C18 H18 120.0 . . ? N1 C19 C14 120.87(14) . . ? N1 C19 C18 119.27(15) . . ? C18 C19 C14 119.86(15) . . ? N2 C21 C22 123.00(16) . . ? N2 C21 C210 116.25(14) . . ? C22 C21 C210 120.74(15) . . ? C21 C22 H22 120.5 . . ? C23 C22 C21 119.04(16) . . ? C23 C22 H22 120.5 . . ? C22 C23 H23 120.2 . . ? C22 C23 C24 119.59(15) . . ? C24 C23 H23 120.2 . . ? C23 C24 C25 123.13(16) . . ? C23 C24 C29 118.32(16) . . ? C25 C24 C29 118.56(17) . . ? C24 C25 H25 119.6 . . ? C26 C25 C24 120.86(17) . . ? C26 C25 H25 119.6 . . ? C25 C26 H26 119.8 . . ? C25 C26 C27 120.33(18) . . ? C27 C26 H26 119.8 . . ? C26 C27 H27 119.7 . . ? C28 C27 C26 120.60(18) . . ? C28 C27 H27 119.7 . . ? C27 C28 H28 120.1 . . ? C27 C28 C29 119.89(16) . . ? C29 C28 H28 120.1 . . ? N2 C29 C24 120.71(15) . . ? N2 C29 C28 119.53(14) . . ? C28 C29 C24 119.76(16) . . ? N31 C31 H31A 109.7 . . ? N31 C31 H31B 109.7 . . ? N31 C31 C32 110.0(2) . . ? H31A C31 H31B 108.2 . . ? C32 C31 H31A 109.7 . . ? C32 C31 H31B 109.7 . . ? C31 C32 H32A 109.4 . . ? C31 C32 H32B 109.4 . . ? C31 C32 C33 111.0(3) . . ? H32A C32 H32B 108.0 . . ? C33 C32 H32A 109.4 . . ? C33 C32 H32B 109.4 . . ? C32 C33 H33A 109.6 . . ? C32 C33 H33B 109.6 . . ? H33A C33 H33B 108.1 . . ? C34 C33 C32 110.5(2) . . ? C34 C33 H33A 109.6 . . ? C34 C33 H33B 109.6 . . ? C33 C34 H34A 109.4 . . ? C33 C34 H34B 109.4 . . ? H34A C34 H34B 108.0 . . ? C35 C34 C33 111.3(3) . . ? C35 C34 H34A 109.4 . . ? C35 C34 H34B 109.4 . . ? N31 C35 C34 111.1(3) . . ? N31 C35 H35A 109.4 . . ? N31 C35 H35B 109.4 . . ? C34 C35 H35A 109.4 . . ? C34 C35 H35B 109.4 . . ? H35A C35 H35B 108.0 . . ? N31 C36 C37 117.69(17) . . ? N32 C36 N31 124.73(17) . . ? N32 C36 C37 117.56(17) . . ? 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 . . ? O21 C210 C21 115.94(15) . . ? O22 C210 O21 125.89(17) . . ? O22 C210 C21 118.15(15) . . ? O11 C110 C11 116.34(13) . . ? O12 C110 O11 125.28(16) . . ? O12 C110 C11 118.37(15) . . ? N4 C41 C42 179.4(3) . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42B 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O11 2.0114(11) . ? Zn1 O21 2.0038(12) . ? Zn1 N1 2.1844(13) . ? Zn1 N2 2.1486(13) . ? Zn1 N32 1.9877(14) . ? O11 C110 1.275(2) . ? O12 C110 1.2358(19) . ? O21 C210 1.274(2) . ? O22 C210 1.232(2) . ? N1 C11 1.318(2) . ? N1 C19 1.372(2) . ? N2 C21 1.320(2) . ? N2 C29 1.369(2) . ? N31 C31 1.469(3) . ? N31 C35 1.470(3) . ? N31 C36 1.352(2) . ? N32 C36 1.289(2) . ? N32 H32 0.82(2) . ? C11 C12 1.410(2) . ? C11 C110 1.517(2) . ? C12 H12 0.9300 . ? C12 C13 1.366(3) . ? C13 H13 0.9300 . ? C13 C14 1.414(2) . ? C14 C15 1.418(3) . ? C14 C19 1.422(2) . ? C15 H15 0.9300 . ? C15 C16 1.363(3) . ? C16 H16 0.9300 . ? C16 C17 1.414(3) . ? C17 H17 0.9300 . ? C17 C18 1.368(2) . ? C18 H18 0.9300 . ? C18 C19 1.410(2) . ? C21 C22 1.408(2) . ? C21 C210 1.521(2) . ? C22 H22 0.9300 . ? C22 C23 1.361(3) . ? C23 H23 0.9300 . ? C23 C24 1.410(3) . ? C24 C25 1.417(3) . ? C24 C29 1.420(2) . ? C25 H25 0.9300 . ? C25 C26 1.358(3) . ? C26 H26 0.9300 . ? C26 C27 1.412(3) . ? C27 H27 0.9300 . ? C27 C28 1.372(3) . ? C28 H28 0.9300 . ? C28 C29 1.409(2) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C31 C32 1.495(4) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C32 C33 1.531(4) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C33 C34 1.527(5) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C34 C35 1.475(6) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.509(3) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C41 C42 1.446(3) . ? C41 N4 1.127(3) . ? C42 H42A 0.9600 . ? C42 H42B 0.9600 . ? C42 H42C 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 N32 H32 O12 0.82(2) 2.23(2) 2.9728(19) 152.4(19) 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 -179.78(14) . . . . ? Zn1 O11 C110 C11 1.55(19) . . . . ? Zn1 O21 C210 O22 -175.93(14) . . . . ? Zn1 O21 C210 C21 2.40(18) . . . . ? Zn1 N1 C11 C12 164.75(13) . . . . ? Zn1 N1 C11 C110 -15.49(17) . . . . ? Zn1 N1 C19 C14 -163.47(12) . . . . ? Zn1 N1 C19 C18 16.2(2) . . . . ? Zn1 N2 C21 C22 -179.02(12) . . . . ? Zn1 N2 C21 C210 1.88(16) . . . . ? Zn1 N2 C29 C24 178.08(10) . . . . ? Zn1 N2 C29 C28 -2.2(2) . . . . ? Zn1 N32 C36 N31 170.33(18) . . . . ? Zn1 N32 C36 C37 -10.9(3) . . . . ? N1 C11 C12 C13 1.7(3) . . . . ? N1 C11 C110 O11 10.4(2) . . . . ? N1 C11 C110 O12 -168.40(15) . . . . ? N2 C21 C22 C23 0.4(2) . . . . ? N2 C21 C210 O21 -2.9(2) . . . . ? N2 C21 C210 O22 175.54(15) . . . . ? N31 C31 C32 C33 -56.9(2) . . . . ? C11 N1 C19 C14 1.4(2) . . . . ? C11 N1 C19 C18 -178.85(15) . . . . ? C11 C12 C13 C14 0.8(2) . . . . ? C12 C11 C110 O11 -169.87(15) . . . . ? C12 C11 C110 O12 11.4(2) . . . . ? C12 C13 C14 C15 178.68(16) . . . . ? C12 C13 C14 C19 -1.9(2) . . . . ? C13 C14 C15 C16 178.74(17) . . . . ? C13 C14 C19 N1 0.9(2) . . . . ? C13 C14 C19 C18 -178.82(15) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C14 C19 N1 -179.71(15) . . . . ? C15 C14 C19 C18 0.6(2) . . . . ? C15 C16 C17 C18 -0.1(3) . . . . ? C16 C17 C18 C19 0.1(3) . . . . ? C17 C18 C19 N1 179.99(16) . . . . ? C17 C18 C19 C14 -0.3(3) . . . . ? C19 N1 C11 C12 -2.8(2) . . . . ? C19 N1 C11 C110 176.97(14) . . . . ? C19 C14 C15 C16 -0.6(3) . . . . ? C21 N2 C29 C24 0.8(2) . . . . ? C21 N2 C29 C28 -179.49(14) . . . . ? C21 C22 C23 C24 0.8(2) . . . . ? C22 C21 C210 O21 177.95(14) . . . . ? C22 C21 C210 O22 -3.6(2) . . . . ? C22 C23 C24 C25 179.22(16) . . . . ? C22 C23 C24 C29 -1.2(2) . . . . ? C23 C24 C25 C26 179.85(17) . . . . ? C23 C24 C29 N2 0.4(2) . . . . ? C23 C24 C29 C28 -179.33(14) . . . . ? C24 C25 C26 C27 -0.7(3) . . . . ? C25 C24 C29 N2 -179.96(14) . . . . ? C25 C24 C29 C28 0.3(2) . . . . ? C25 C26 C27 C28 0.6(3) . . . . ? C26 C27 C28 C29 0.0(3) . . . . ? C27 C28 C29 N2 179.86(15) . . . . ? C27 C28 C29 C24 -0.4(2) . . . . ? C29 N2 C21 C22 -1.2(2) . . . . ? C29 N2 C21 C210 179.69(13) . . . . ? C29 C24 C25 C26 0.3(3) . . . . ? C31 N31 C35 C34 -61.2(3) . . . . ? C31 N31 C36 N32 -13.6(4) . . . . ? C31 N31 C36 C37 167.6(2) . . . . ? C31 C32 C33 C34 52.2(4) . . . . ? C32 C33 C34 C35 -51.7(4) . . . . ? C33 C34 C35 N31 56.2(3) . . . . ? C35 N31 C31 C32 61.2(3) . . . . ? C35 N31 C36 N32 -164.3(3) . . . . ? C35 N31 C36 C37 17.0(4) . . . . ? C36 N31 C31 C32 -92.4(3) . . . . ? C36 N31 C35 C34 92.2(3) . . . . ? C210 C21 C22 C23 179.50(14) . . . . ? C110 C11 C12 C13 -178.04(15) . . . . ?