#------------------------------------------------------------------------------ #$Date: 2020-05-14 06:08:43 +0300 (Thu, 14 May 2020) $ #$Revision: 252047 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240517.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_7240517 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 H34 N4 O4 Zn' _chemical_formula_sum 'C30 H34 N4 O4 Zn' _chemical_formula_weight 579.98 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _audit_creation_date 2019-12-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-12-19 deposited with the CCDC. 2020-04-29 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.748(4) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.8913(6) _cell_length_b 7.6503(3) _cell_length_c 16.1369(8) _cell_measurement_reflns_used 4686 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 29.9480 _cell_measurement_theta_min 3.3860 _cell_volume 1467.32(12) _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 5.2466 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 -87.00 -60.00 1.00 4.00 -- -14.59-178.00 0.00 27 2 \w -43.00 38.00 1.00 4.00 -- 14.67 -57.00 120.00 81 3 \w -57.00 36.00 1.00 4.00 -- 14.67 -57.00-120.00 93 ; _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 -0.0566525000 _diffrn_orient_matrix_UB_12 -0.0223008000 _diffrn_orient_matrix_UB_13 0.0077123000 _diffrn_orient_matrix_UB_21 -0.0033251000 _diffrn_orient_matrix_UB_22 -0.0472510000 _diffrn_orient_matrix_UB_23 -0.0378260000 _diffrn_orient_matrix_UB_31 0.0184884000 _diffrn_orient_matrix_UB_32 -0.0765891000 _diffrn_orient_matrix_UB_33 0.0210461000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0192 _diffrn_reflns_av_unetI/netI 0.0278 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 7093 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 27.500 _diffrn_reflns_theta_min 2.947 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.877 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.65107 _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 1.313 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.9 _exptl_crystal_size_mid 0.7 _exptl_crystal_size_min 0.5 _refine_diff_density_max 0.339 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 182 _refine_ls_number_reflns 3365 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.113 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0304 _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^)+(0.0348P)^2^+1.1087P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0832 _refine_ls_wR_factor_ref 0.0852 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3014 _reflns_number_total 3365 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03192e3.cif _cod_data_source_block 1 _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 7240517 _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 0.540 _shelx_estimated_absorpt_t_min 0.419 _shelx_res_file ; TITL mob683 in P2(1)/n mob683.res created by SHELXL-2018/3 at 11:08:01 on 16-Dec-2019 CELL 0.71073 11.8913 7.6503 16.1369 90 91.748 90 ZERR 2 0.0006 0.0003 0.0008 0 0.004 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O Zn UNIT 60 68 8 8 2 EQIV $1 1-X,1-Y,1-Z EQIV $2 +X,-1+Y,+Z L.S. 10 PLAN 10 SIZE 1.2 1 0.8 MPLA N1 C11 C12 C13 C14 C15 C16 C17 C18 C19 MPLA N1_$1 C11_$1 C12_$1 C13_$1 C14_$1 C15_$1 C16_$1 C17_$1 C18_$1 C19_$1 HTAB N2 O12_$2 BOND $H LIST 6 MORE -1 CONF fmap 2 acta 52 SHEL 30 0.7696 OMIT -2 0 2 OMIT 2 0 0 REM REM REM WGHT 0.034800 1.108700 FVAR 66.77281 ZN1 5 0.500000 0.500000 0.500000 10.50000 0.01166 0.00977 = 0.01453 0.00200 -0.00039 -0.00070 O11 4 0.481821 0.724501 0.431235 11.00000 0.01715 0.01201 = 0.01774 0.00262 -0.00452 -0.00142 O12 4 0.555038 0.986494 0.404279 11.00000 0.02887 0.01233 = 0.02032 0.00438 -0.00189 -0.00344 N1 3 0.647824 0.661329 0.545411 11.00000 0.01283 0.01496 = 0.01288 -0.00037 -0.00003 0.00010 N2 3 0.596751 0.374368 0.400951 11.00000 0.01511 0.01083 = 0.01631 0.00155 0.00059 -0.00076 C11 1 0.644119 0.816538 0.509689 11.00000 0.01405 0.01420 = 0.01561 -0.00131 0.00085 -0.00013 C12 1 0.719961 0.952167 0.529824 11.00000 0.02289 0.01429 = 0.03363 -0.00098 -0.00353 -0.00387 AFIX 43 H12 2 0.714029 1.059746 0.503211 11.00000 -1.20000 AFIX 0 C13 1 0.802344 0.923666 0.588942 11.00000 0.02213 0.02232 = 0.03871 -0.00889 -0.00685 -0.00716 AFIX 43 H13 2 0.852893 1.012159 0.603310 11.00000 -1.20000 AFIX 0 C14 1 0.810380 0.759871 0.627991 11.00000 0.01605 0.02456 = 0.02091 -0.00849 -0.00167 0.00156 C15 1 0.891650 0.721437 0.691029 11.00000 0.01654 0.03630 = 0.02864 -0.01454 -0.00742 0.00251 AFIX 43 H15 2 0.943311 0.806891 0.707430 11.00000 -1.20000 AFIX 0 C16 1 0.895853 0.561763 0.728256 11.00000 0.01828 0.04505 = 0.02031 -0.00660 -0.00758 0.01022 AFIX 43 H16 2 0.949214 0.539124 0.770216 11.00000 -1.20000 AFIX 0 C17 1 0.818461 0.430456 0.702663 11.00000 0.01988 0.03711 = 0.02034 0.00616 0.00009 0.00769 AFIX 43 H17 2 0.822756 0.320509 0.727141 11.00000 -1.20000 AFIX 0 C18 1 0.737325 0.462470 0.642462 11.00000 0.01499 0.02570 = 0.01936 0.00412 -0.00071 -0.00043 AFIX 43 H18 2 0.686644 0.375151 0.626687 11.00000 -1.20000 AFIX 0 C19 1 0.730967 0.629022 0.604376 11.00000 0.01176 0.02190 = 0.01265 -0.00210 0.00033 0.00048 C21 1 0.719470 0.397517 0.409376 11.00000 0.01452 0.01890 = 0.02181 -0.00239 0.00197 -0.00116 AFIX 23 H21A 2 0.744274 0.362665 0.464766 11.00000 -1.20000 H21B 2 0.737199 0.520425 0.402885 11.00000 -1.20000 AFIX 0 C22 1 0.784382 0.291689 0.346002 11.00000 0.01872 0.02409 = 0.03098 -0.00521 0.00516 0.00253 AFIX 23 H22A 2 0.864144 0.316619 0.352496 11.00000 -1.20000 H22B 2 0.773374 0.167833 0.355738 11.00000 -1.20000 AFIX 0 C23 1 0.744141 0.337280 0.258570 11.00000 0.03124 0.01645 = 0.02509 -0.00073 0.01462 -0.00020 AFIX 23 H23A 2 0.780625 0.261491 0.219388 11.00000 -1.20000 H23B 2 0.764617 0.457006 0.246221 11.00000 -1.20000 AFIX 0 C24 1 0.617303 0.316230 0.249224 11.00000 0.03133 0.02674 = 0.01617 -0.00091 0.00066 0.00124 AFIX 23 H24A 2 0.597968 0.193426 0.253362 11.00000 -1.20000 H24B 2 0.592204 0.357361 0.194889 11.00000 -1.20000 AFIX 0 C25 1 0.557342 0.418585 0.315730 11.00000 0.02013 0.02300 = 0.01665 0.00218 -0.00048 0.00159 AFIX 23 H25A 2 0.568760 0.542538 0.306535 11.00000 -1.20000 H25B 2 0.477218 0.395687 0.310380 11.00000 -1.20000 AFIX 0 C110 1 0.552536 0.846989 0.442705 11.00000 0.01702 0.01187 = 0.01328 -0.00130 0.00103 0.00054 H2 2 0.588499 0.272992 0.409582 11.00000 0.02357 HKLF 4 REM mob683 in P2(1)/n REM wR2 = 0.0852, GooF = S = 1.113, Restrained GooF = 1.113 for all data REM R1 = 0.0304 for 3014 Fo > 4sig(Fo) and 0.0346 for all 3365 data REM 182 parameters refined using 0 restraints END WGHT 0.0348 1.1087 REM Highest difference peak 0.339, deepest hole -0.323, 1-sigma level 0.062 Q1 1 0.5983 0.8280 0.4800 11.00000 0.05 0.34 Q2 1 0.6884 0.6453 0.5767 11.00000 0.05 0.26 Q3 1 0.6775 0.8832 0.5194 11.00000 0.05 0.24 Q4 1 0.7379 0.5487 0.6164 11.00000 0.05 0.24 Q5 1 0.7630 0.7000 0.6212 11.00000 0.05 0.24 Q6 1 0.6992 0.8712 0.5047 11.00000 0.05 0.23 Q7 1 0.5800 0.3961 0.3565 11.00000 0.05 0.22 Q8 1 0.9980 0.4363 0.5180 11.00000 0.05 0.21 Q9 1 0.8463 0.7290 0.6585 11.00000 0.05 0.21 Q10 1 0.6363 0.7489 0.5349 11.00000 0.05 0.21 ; _shelx_res_checksum 88832 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 0.500000 0.500000 0.500000 0.01200(9) Uani 1 2 d S T P . . O11 O 0.48182(10) 0.72450(15) 0.43123(7) 0.0157(3) Uani 1 1 d . . . . . O12 O 0.55504(12) 0.98649(15) 0.40428(8) 0.0206(3) Uani 1 1 d . . . . . N1 N 0.64782(12) 0.66133(19) 0.54541(9) 0.0136(3) Uani 1 1 d . . . . . N2 N 0.59675(12) 0.37437(19) 0.40095(9) 0.0141(3) Uani 1 1 d . . . . . C11 C 0.64412(14) 0.8165(2) 0.50969(10) 0.0146(3) Uani 1 1 d . . . . . C12 C 0.71996(17) 0.9522(2) 0.52982(13) 0.0237(4) Uani 1 1 d . . . . . H12 H 0.714029 1.059746 0.503211 0.028 Uiso 1 1 calc R . . . . C13 C 0.80234(17) 0.9237(3) 0.58894(14) 0.0279(4) Uani 1 1 d . . . . . H13 H 0.852893 1.012159 0.603310 0.033 Uiso 1 1 calc R . . . . C14 C 0.81038(15) 0.7599(3) 0.62799(12) 0.0206(4) Uani 1 1 d . . . . . C15 C 0.89165(16) 0.7214(3) 0.69103(13) 0.0273(4) Uani 1 1 d . . . . . H15 H 0.943311 0.806891 0.707430 0.033 Uiso 1 1 calc R . . . . C16 C 0.89585(17) 0.5618(3) 0.72826(12) 0.0280(5) Uani 1 1 d . . . . . H16 H 0.949214 0.539124 0.770216 0.034 Uiso 1 1 calc R . . . . C17 C 0.81846(16) 0.4305(3) 0.70266(12) 0.0258(4) Uani 1 1 d . . . . . H17 H 0.822756 0.320509 0.727141 0.031 Uiso 1 1 calc R . . . . C18 C 0.73733(15) 0.4625(3) 0.64246(11) 0.0200(4) Uani 1 1 d . . . . . H18 H 0.686644 0.375151 0.626687 0.024 Uiso 1 1 calc R . . . . C19 C 0.73097(14) 0.6290(2) 0.60438(10) 0.0154(3) Uani 1 1 d . . . . . C21 C 0.71947(15) 0.3975(2) 0.40938(11) 0.0184(4) Uani 1 1 d . . . . . H21A H 0.744274 0.362665 0.464766 0.022 Uiso 1 1 calc R . . . . H21B H 0.737199 0.520425 0.402885 0.022 Uiso 1 1 calc R . . . . C22 C 0.78438(16) 0.2917(3) 0.34600(13) 0.0245(4) Uani 1 1 d . . . . . H22A H 0.864144 0.316619 0.352496 0.029 Uiso 1 1 calc R . . . . H22B H 0.773374 0.167833 0.355738 0.029 Uiso 1 1 calc R . . . . C23 C 0.74414(18) 0.3373(3) 0.25857(12) 0.0240(4) Uani 1 1 d . . . . . H23A H 0.780625 0.261491 0.219388 0.029 Uiso 1 1 calc R . . . . H23B H 0.764617 0.457006 0.246221 0.029 Uiso 1 1 calc R . . . . C24 C 0.61730(17) 0.3162(3) 0.24922(12) 0.0247(4) Uani 1 1 d . . . . . H24A H 0.597968 0.193426 0.253362 0.030 Uiso 1 1 calc R . . . . H24B H 0.592204 0.357361 0.194889 0.030 Uiso 1 1 calc R . . . . C25 C 0.55734(16) 0.4186(2) 0.31573(11) 0.0200(4) Uani 1 1 d . . . . . H25A H 0.568760 0.542538 0.306535 0.024 Uiso 1 1 calc R . . . . H25B H 0.477218 0.395687 0.310380 0.024 Uiso 1 1 calc R . . . . C110 C 0.55254(14) 0.8470(2) 0.44270(10) 0.0140(3) Uani 1 1 d . . . . . H2 H 0.588(2) 0.273(3) 0.4096(14) 0.024(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 0.01166(14) 0.00977(14) 0.01453(14) 0.00200(10) -0.00039(10) -0.00070(10) O11 0.0171(6) 0.0120(5) 0.0177(6) 0.0026(5) -0.0045(5) -0.0014(5) O12 0.0289(7) 0.0123(6) 0.0203(6) 0.0044(5) -0.0019(5) -0.0034(5) N1 0.0128(7) 0.0150(7) 0.0129(7) -0.0004(5) 0.0000(5) 0.0001(5) N2 0.0151(7) 0.0108(7) 0.0163(7) 0.0015(6) 0.0006(5) -0.0008(6) C11 0.0141(8) 0.0142(8) 0.0156(8) -0.0013(6) 0.0008(6) -0.0001(6) C12 0.0229(10) 0.0143(8) 0.0336(11) -0.0010(8) -0.0035(8) -0.0039(7) C13 0.0221(10) 0.0223(10) 0.0387(12) -0.0089(9) -0.0068(8) -0.0072(8) C14 0.0161(9) 0.0246(9) 0.0209(9) -0.0085(7) -0.0017(7) 0.0016(7) C15 0.0165(9) 0.0363(11) 0.0286(10) -0.0145(9) -0.0074(8) 0.0025(8) C16 0.0183(9) 0.0451(12) 0.0203(9) -0.0066(9) -0.0076(7) 0.0102(9) C17 0.0199(9) 0.0371(11) 0.0203(9) 0.0062(8) 0.0001(7) 0.0077(9) C18 0.0150(8) 0.0257(9) 0.0194(9) 0.0041(7) -0.0007(7) -0.0004(7) C19 0.0118(8) 0.0219(9) 0.0126(8) -0.0021(7) 0.0003(6) 0.0005(7) C21 0.0145(8) 0.0189(8) 0.0218(9) -0.0024(7) 0.0020(7) -0.0012(7) C22 0.0187(9) 0.0241(9) 0.0310(10) -0.0052(8) 0.0052(8) 0.0025(8) C23 0.0312(10) 0.0164(9) 0.0251(10) -0.0007(7) 0.0146(8) -0.0002(8) C24 0.0313(11) 0.0267(10) 0.0162(9) -0.0009(7) 0.0007(7) 0.0012(8) C25 0.0201(9) 0.0230(9) 0.0167(8) 0.0022(7) -0.0005(7) 0.0016(7) C110 0.0170(8) 0.0119(7) 0.0133(8) -0.0013(6) 0.0010(6) 0.0005(6) 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 O11 180.0 . 3_666 ? O11 Zn1 N1 77.62(5) . . ? O11 Zn1 N1 102.38(5) 3_666 . ? O11 Zn1 N1 102.38(5) . 3_666 ? O11 Zn1 N1 77.62(5) 3_666 3_666 ? O11 Zn1 N2 91.23(5) . . ? O11 Zn1 N2 88.77(5) . 3_666 ? O11 Zn1 N2 91.23(5) 3_666 3_666 ? O11 Zn1 N2 88.77(5) 3_666 . ? N1 Zn1 N1 180.0 3_666 . ? N2 Zn1 N1 86.84(5) 3_666 . ? N2 Zn1 N1 86.84(5) . 3_666 ? N2 Zn1 N1 93.16(5) . . ? N2 Zn1 N1 93.16(5) 3_666 3_666 ? N2 Zn1 N2 180.0 . 3_666 ? C110 O11 Zn1 118.73(11) . . ? C11 N1 Zn1 109.61(11) . . ? C11 N1 C19 118.56(15) . . ? C19 N1 Zn1 131.68(12) . . ? Zn1 N2 H2 103.1(17) . . ? C21 N2 Zn1 114.59(11) . . ? C21 N2 C25 110.09(14) . . ? C21 N2 H2 103.2(17) . . ? C25 N2 Zn1 114.50(11) . . ? C25 N2 H2 110.4(17) . . ? N1 C11 C12 123.38(16) . . ? N1 C11 C110 117.35(15) . . ? C12 C11 C110 119.27(16) . . ? C11 C12 H12 120.5 . . ? C13 C12 C11 119.05(18) . . ? C13 C12 H12 120.5 . . ? C12 C13 H13 120.2 . . ? C12 C13 C14 119.60(18) . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 122.99(18) . . ? C13 C14 C19 118.22(17) . . ? C15 C14 C19 118.76(18) . . ? C14 C15 H15 119.3 . . ? C16 C15 C14 121.31(19) . . ? C16 C15 H15 119.3 . . ? C15 C16 H16 120.2 . . ? C15 C16 C17 119.55(18) . . ? C17 C16 H16 120.2 . . ? C16 C17 H17 119.4 . . ? C18 C17 C16 121.2(2) . . ? C18 C17 H17 119.4 . . ? C17 C18 H18 120.1 . . ? C17 C18 C19 119.72(18) . . ? C19 C18 H18 120.1 . . ? N1 C19 C14 121.18(16) . . ? N1 C19 C18 119.37(16) . . ? C18 C19 C14 119.45(16) . . ? N2 C21 H21A 108.9 . . ? N2 C21 H21B 108.9 . . ? N2 C21 C22 113.15(15) . . ? H21A C21 H21B 107.8 . . ? C22 C21 H21A 108.9 . . ? C22 C21 H21B 108.9 . . ? C21 C22 H22A 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? C23 C22 C21 110.40(16) . . ? C23 C22 H22A 109.6 . . ? C23 C22 H22B 109.6 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 C24 110.61(16) . . ? H23A C23 H23B 108.1 . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C23 C24 H24A 109.4 . . ? C23 C24 H24B 109.4 . . ? C23 C24 C25 111.11(16) . . ? H24A C24 H24B 108.0 . . ? C25 C24 H24A 109.4 . . ? C25 C24 H24B 109.4 . . ? N2 C25 C24 113.32(15) . . ? N2 C25 H25A 108.9 . . ? N2 C25 H25B 108.9 . . ? C24 C25 H25A 108.9 . . ? C24 C25 H25B 108.9 . . ? H25A C25 H25B 107.7 . . ? O11 C110 C11 116.44(14) . . ? O12 C110 O11 126.22(16) . . ? O12 C110 C11 117.33(15) . . ? 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 2.0526(12) . ? Zn1 O11 2.0526(12) 3_666 ? Zn1 N1 2.2520(14) . ? Zn1 N1 2.2520(14) 3_666 ? Zn1 N2 2.2168(15) . ? Zn1 N2 2.2168(15) 3_666 ? O11 C110 1.269(2) . ? O12 C110 1.235(2) . ? N1 C11 1.320(2) . ? N1 C19 1.374(2) . ? N2 C21 1.472(2) . ? N2 C25 1.478(2) . ? N2 H2 0.79(2) . ? C11 C12 1.406(2) . ? C11 C110 1.529(2) . ? C12 H12 0.9300 . ? C12 C13 1.364(3) . ? C13 H13 0.9300 . ? C13 C14 1.405(3) . ? C14 C15 1.413(3) . ? C14 C19 1.420(3) . ? C15 H15 0.9300 . ? C15 C16 1.362(3) . ? C16 H16 0.9300 . ? C16 C17 1.415(3) . ? C17 H17 0.9300 . ? C17 C18 1.370(3) . ? C18 H18 0.9300 . ? C18 C19 1.416(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 C22 1.531(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C22 C23 1.517(3) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C23 C24 1.520(3) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C24 C25 1.523(3) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? 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 N2 H2 O12 0.79(2) 2.23(2) 3.0093(19) 167(2) 1_545 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 177.27(14) . . . . ? Zn1 O11 C110 C11 -1.71(19) . . . . ? Zn1 N1 C11 C12 174.99(15) . . . . ? Zn1 N1 C11 C110 -5.49(18) . . . . ? Zn1 N1 C19 C14 -173.88(12) . . . . ? Zn1 N1 C19 C18 5.9(2) . . . . ? Zn1 N2 C21 C22 173.27(12) . . . . ? Zn1 N2 C25 C24 -174.06(12) . . . . ? N1 C11 C12 C13 0.3(3) . . . . ? N1 C11 C110 O11 5.2(2) . . . . ? N1 C11 C110 O12 -173.86(15) . . . . ? N2 C21 C22 C23 56.2(2) . . . . ? C11 N1 C19 C14 1.2(2) . . . . ? C11 N1 C19 C18 -179.05(16) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C11 C110 O11 -175.24(16) . . . . ? C12 C11 C110 O12 5.7(2) . . . . ? C12 C13 C14 C15 -178.5(2) . . . . ? C12 C13 C14 C19 -0.3(3) . . . . ? C13 C14 C15 C16 179.08(19) . . . . ? C13 C14 C19 N1 -0.5(3) . . . . ? C13 C14 C19 C18 179.75(17) . . . . ? C14 C15 C16 C17 0.9(3) . . . . ? C15 C14 C19 N1 177.80(17) . . . . ? C15 C14 C19 C18 -2.0(3) . . . . ? C15 C16 C17 C18 -1.7(3) . . . . ? C16 C17 C18 C19 0.6(3) . . . . ? C17 C18 C19 N1 -178.54(17) . . . . ? C17 C18 C19 C14 1.2(3) . . . . ? C19 N1 C11 C12 -1.1(3) . . . . ? C19 N1 C11 C110 178.44(14) . . . . ? C19 C14 C15 C16 0.9(3) . . . . ? C21 N2 C25 C24 55.1(2) . . . . ? C21 C22 C23 C24 -53.7(2) . . . . ? C22 C23 C24 C25 53.2(2) . . . . ? C23 C24 C25 N2 -54.6(2) . . . . ? C25 N2 C21 C22 -56.0(2) . . . . ? C110 C11 C12 C13 -179.24(18) . . . . ?