#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:42:26 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258103 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240527.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_7240527 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 'C20 H12 Cl N2 O4 Zn, C4 H10 N' _chemical_formula_sum 'C24 H22 Cl N3 O4 Zn' _chemical_formula_weight 517.26 _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_Hall '-P 2yc' _space_group_name_H-M_alt 'P 1 2/c 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 91.675(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.5603(6) _cell_length_b 6.7219(8) _cell_length_c 17.1475(12) _cell_measurement_reflns_used 2190 _cell_measurement_temperature 150.00(10) _cell_measurement_theta_max 29.8650 _cell_measurement_theta_min 3.2190 _cell_volume 1101.49(17) _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 -104.00 -70.00 1.00 32.50 -- -14.36-178.00 0.00 34 2 \w -65.00 60.00 1.00 32.50 -- 14.52 -19.00 -30.00 125 3 \w 9.00 56.00 1.00 32.50 -- 14.52 -99.00-150.00 47 ; _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 -0.0308945000 _diffrn_orient_matrix_UB_12 0.0959233000 _diffrn_orient_matrix_UB_13 -0.0011658000 _diffrn_orient_matrix_UB_21 -0.0586495000 _diffrn_orient_matrix_UB_22 -0.0374708000 _diffrn_orient_matrix_UB_23 0.0197315000 _diffrn_orient_matrix_UB_31 0.0333234000 _diffrn_orient_matrix_UB_32 0.0232269000 _diffrn_orient_matrix_UB_33 0.0363547000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_unetI/netI 0.0441 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5444 _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 27.499 _diffrn_reflns_theta_min 2.376 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 1.274 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61377 _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 1.560 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 532 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.582 _refine_diff_density_min -0.333 _refine_diff_density_rms 0.070 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 155 _refine_ls_number_reflns 2536 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0350 _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^)+(0.0444P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0819 _refine_ls_wR_factor_ref 0.0867 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2178 _reflns_number_total 2536 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03192e3.cif _cod_data_source_block 9 _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 7240527 _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 0.883 _shelx_estimated_absorpt_t_min 0.785 _shelx_res_file ; TITL mob667 in P2/c mob667.res created by SHELXL-2018/3 at 11:22:13 on 16-Dec-2019 CELL 0.71073 9.5603 6.7219 17.1475 90 91.675 90 ZERR 2 0.0006 0.0008 0.0012 0 0.007 0 LATT 1 SYMM -X,+Y,0.5-Z SFAC C H Cl N O Zn UNIT 48 44 2 6 8 2 EQIV $1 1-X,+Y,1.5-Z L.S. 10 PLAN 10 SIZE 0.2 0.15 0.1 MPLA 4 N1 O11 N1_$1 O11_$1 Zn1 MPLA N1 C11 C12 C13 C14 C19 MPLA N1_$1 C11_$1 C12_$1 C13_$1 C14_$1 C19_$1 MPLA N1 C11 C12 C13 C14 C19 C15 C16 C17 C18 MPLA N1_$1 C11_$1 C12_$1 C13_$1 C14_$1 C19_$1 C15_$1 C16_$1 C17_$1 C18_$1 HTAB N2 O12 MORE -1 HTAB 2.00000 BOND $H CONF LIST 6 fmap 2 acta MERG 2 SHEL 30 0.7696 REM REM REM WGHT 0.044400 FVAR 2.70667 ZN1 6 0.500000 0.813559 0.750000 10.50000 0.01558 0.03521 = 0.01513 0.00000 0.00080 0.00000 CL1 3 0.500000 1.150817 0.750000 10.50000 0.04246 0.03512 = 0.01898 0.00000 -0.00237 0.00000 O11 5 0.306753 0.711858 0.727266 11.00000 0.01956 0.04834 = 0.01411 -0.00130 0.00089 -0.00466 O12 5 0.142143 0.669452 0.635005 11.00000 0.01639 0.04999 = 0.02261 0.00104 -0.00052 -0.00271 N1 4 0.502096 0.755159 0.621715 11.00000 0.01685 0.02586 = 0.01612 0.00048 0.00143 0.00068 N2 4 0.000000 0.485104 0.750000 10.50000 0.02193 0.03128 = 0.03365 0.00000 0.00843 0.00000 C11 1 0.372889 0.727225 0.595499 11.00000 0.01825 0.02297 = 0.01807 0.00048 0.00014 0.00184 C12 1 0.334960 0.717304 0.515622 11.00000 0.02081 0.02493 = 0.01930 -0.00050 -0.00249 -0.00114 AFIX 43 H12 2 0.242262 0.696393 0.499777 11.00000 -1.20000 AFIX 0 C13 1 0.435468 0.738663 0.462220 11.00000 0.02690 0.02329 = 0.01627 -0.00060 -0.00221 0.00049 AFIX 43 H13 2 0.411959 0.735281 0.409224 11.00000 -1.20000 AFIX 0 C14 1 0.575984 0.766068 0.487325 11.00000 0.02441 0.01970 = 0.01623 -0.00022 0.00340 0.00323 C15 1 0.686747 0.784782 0.435536 11.00000 0.02985 0.02797 = 0.01579 0.00153 0.00465 0.00536 AFIX 43 H15 2 0.668189 0.782239 0.382002 11.00000 -1.20000 AFIX 0 C16 1 0.821143 0.806627 0.463216 11.00000 0.02498 0.04336 = 0.02191 0.00438 0.01054 0.00584 AFIX 43 H16 2 0.893512 0.819739 0.428500 11.00000 -1.20000 AFIX 0 C17 1 0.850661 0.809392 0.544117 11.00000 0.01784 0.04924 = 0.02668 0.00541 0.00216 0.00303 AFIX 43 H17 2 0.942770 0.821397 0.562482 11.00000 -1.20000 AFIX 0 C18 1 0.745659 0.794659 0.595700 11.00000 0.02012 0.04439 = 0.01735 0.00258 0.00132 0.00265 AFIX 43 H18 2 0.766365 0.798977 0.649004 11.00000 -1.20000 AFIX 0 C19 1 0.606080 0.772955 0.568944 11.00000 0.02040 0.02470 = 0.01545 -0.00023 0.00352 0.00309 C21 1 -0.100891 0.354575 0.704998 11.00000 0.02700 0.05461 = 0.04894 -0.01807 0.00774 -0.00147 AFIX 23 H21A 2 -0.196663 0.396208 0.712651 11.00000 -1.20000 H21B 2 -0.082483 0.357971 0.649684 11.00000 -1.20000 AFIX 0 C22 1 -0.075627 0.152683 0.737528 11.00000 0.11565 0.05484 = 0.04178 -0.00908 0.01173 -0.03997 AFIX 23 H22A 2 -0.094327 0.051508 0.698257 11.00000 -1.20000 H22B 2 -0.134534 0.128335 0.781636 11.00000 -1.20000 AFIX 0 C110 1 0.264624 0.702030 0.656464 11.00000 0.01873 0.02637 = 0.02189 -0.00065 0.00047 0.00080 H2 2 0.042025 0.573520 0.720888 11.00000 0.04319 HKLF 4 REM mob667 in P2/c REM wR2 = 0.0867, GooF = S = 1.033, Restrained GooF = 1.033 for all data REM R1 = 0.0350 for 2178 Fo > 4sig(Fo) and 0.0436 for all 2536 data REM 155 parameters refined using 0 restraints END WGHT 0.0444 0.0000 REM Instructions for potential hydrogen bonds HTAB C18 O11_$1 EQIV $2 -x, y, -z+3/2 HTAB C21 O11_$2 HTAB N2 O12 REM Highest difference peak 0.582, deepest hole -0.333, 1-sigma level 0.070 Q1 1 0.4703 0.9793 0.7259 11.00000 0.05 0.58 Q2 1 0.4254 0.7586 0.6008 11.00000 0.05 0.36 Q3 1 0.4649 0.6702 0.7287 11.00000 0.05 0.34 Q4 1 0.5197 0.7383 0.6419 11.00000 0.05 0.33 Q5 1 0.3578 0.7227 0.5594 11.00000 0.05 0.31 Q6 1 0.3223 0.7607 0.6291 11.00000 0.05 0.31 Q7 1 0.5655 0.7427 0.7167 11.00000 0.05 0.29 Q8 1 0.5871 0.7771 0.5290 11.00000 0.05 0.29 Q9 1 0.7943 0.8560 0.5705 11.00000 0.05 0.29 Q10 1 0.6199 0.9996 0.7100 11.00000 0.05 0.28 ; _shelx_res_checksum 53899 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, 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 0.81356(6) 0.750000 0.02196(12) Uani 1 2 d S T P . . Cl1 Cl 0.500000 1.15082(13) 0.750000 0.0322(2) Uani 1 2 d S T P . . O11 O 0.30675(14) 0.7119(3) 0.72727(7) 0.0273(4) Uani 1 1 d . . . . . O12 O 0.14214(13) 0.6695(3) 0.63501(8) 0.0297(4) Uani 1 1 d . . . . . N1 N 0.50210(16) 0.7552(3) 0.62172(9) 0.0196(4) Uani 1 1 d . . . . . N2 N 0.000000 0.4851(5) 0.750000 0.0288(6) Uani 1 2 d S T P . . C11 C 0.37289(19) 0.7272(3) 0.59550(11) 0.0198(4) Uani 1 1 d . . . . . C12 C 0.3350(2) 0.7173(3) 0.51562(11) 0.0217(5) Uani 1 1 d . . . . . H12 H 0.242262 0.696393 0.499777 0.026 Uiso 1 1 calc R . . . . C13 C 0.4355(2) 0.7387(3) 0.46222(11) 0.0222(4) Uani 1 1 d . . . . . H13 H 0.411959 0.735281 0.409224 0.027 Uiso 1 1 calc R . . . . C14 C 0.5760(2) 0.7661(3) 0.48733(11) 0.0201(4) Uani 1 1 d . . . . . C15 C 0.6867(2) 0.7848(3) 0.43554(11) 0.0245(5) Uani 1 1 d . . . . . H15 H 0.668189 0.782239 0.382002 0.029 Uiso 1 1 calc R . . . . C16 C 0.8211(2) 0.8066(4) 0.46322(12) 0.0299(5) Uani 1 1 d . . . . . H16 H 0.893512 0.819739 0.428500 0.036 Uiso 1 1 calc R . . . . C17 C 0.8507(2) 0.8094(4) 0.54412(12) 0.0312(6) Uani 1 1 d . . . . . H17 H 0.942770 0.821397 0.562482 0.037 Uiso 1 1 calc R . . . . C18 C 0.7457(2) 0.7947(4) 0.59570(12) 0.0273(5) Uani 1 1 d . . . . . H18 H 0.766365 0.798977 0.649004 0.033 Uiso 1 1 calc R . . . . C19 C 0.6061(2) 0.7730(3) 0.56894(11) 0.0201(4) Uani 1 1 d . . . . . C21 C -0.1009(2) 0.3546(5) 0.70500(15) 0.0434(7) Uani 1 1 d . . . . . H21A H -0.196663 0.396208 0.712651 0.052 Uiso 1 1 calc R . . . . H21B H -0.082483 0.357971 0.649684 0.052 Uiso 1 1 calc R . . . . C22 C -0.0756(4) 0.1527(6) 0.73753(17) 0.0706(11) Uani 1 1 d . . . . . H22A H -0.094327 0.051508 0.698257 0.085 Uiso 1 1 calc R . . . . H22B H -0.134534 0.128335 0.781636 0.085 Uiso 1 1 calc R . . . . C110 C 0.2646(2) 0.7020(4) 0.65646(11) 0.0223(5) Uani 1 1 d . . . . . H2 H 0.042(3) 0.574(4) 0.7209(14) 0.043(7) 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 0.01558(16) 0.0352(3) 0.01513(17) 0.000 0.00080(11) 0.000 Cl1 0.0425(4) 0.0351(5) 0.0190(3) 0.000 -0.0024(3) 0.000 O11 0.0196(6) 0.0483(12) 0.0141(7) -0.0013(6) 0.0009(5) -0.0047(7) O12 0.0164(6) 0.0500(12) 0.0226(7) 0.0010(7) -0.0005(6) -0.0027(7) N1 0.0168(7) 0.0259(11) 0.0161(8) 0.0005(7) 0.0014(6) 0.0007(7) N2 0.0219(11) 0.0313(18) 0.0337(14) 0.000 0.0084(11) 0.000 C11 0.0182(9) 0.0230(13) 0.0181(9) 0.0005(8) 0.0001(7) 0.0018(8) C12 0.0208(9) 0.0249(13) 0.0193(9) -0.0005(8) -0.0025(8) -0.0011(9) C13 0.0269(10) 0.0233(12) 0.0163(9) -0.0006(8) -0.0022(8) 0.0005(9) C14 0.0244(9) 0.0197(12) 0.0162(9) -0.0002(8) 0.0034(7) 0.0032(9) C15 0.0298(10) 0.0280(14) 0.0158(9) 0.0015(8) 0.0047(8) 0.0054(10) C16 0.0250(10) 0.0434(16) 0.0219(10) 0.0044(9) 0.0105(8) 0.0058(10) C17 0.0178(9) 0.0492(17) 0.0267(11) 0.0054(10) 0.0022(8) 0.0030(10) C18 0.0201(9) 0.0444(16) 0.0173(9) 0.0026(9) 0.0013(8) 0.0027(10) C19 0.0204(9) 0.0247(13) 0.0154(9) -0.0002(8) 0.0035(7) 0.0031(9) C21 0.0270(11) 0.055(2) 0.0489(15) -0.0181(13) 0.0077(10) -0.0015(12) C22 0.116(3) 0.055(2) 0.0418(17) -0.0091(14) 0.0117(18) -0.040(2) C110 0.0187(9) 0.0264(13) 0.0219(10) -0.0006(9) 0.0005(8) 0.0008(9) 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 Cl1 110.01(5) 2_656 . ? O11 Zn1 Cl1 110.01(5) . . ? O11 Zn1 O11 139.98(11) . 2_656 ? O11 Zn1 N1 77.45(6) 2_656 2_656 ? O11 Zn1 N1 77.45(6) . . ? O11 Zn1 N1 95.57(6) 2_656 . ? O11 Zn1 N1 95.57(6) . 2_656 ? N1 Zn1 Cl1 100.12(5) 2_656 . ? N1 Zn1 Cl1 100.12(5) . . ? N1 Zn1 N1 159.77(10) . 2_656 ? C110 O11 Zn1 118.04(13) . . ? C11 N1 Zn1 109.03(12) . . ? C11 N1 C19 118.64(15) . . ? C19 N1 Zn1 131.51(12) . . ? C21 N2 C21 108.4(3) 2_556 . ? C21 N2 H2 113.6(17) 2_556 2_556 ? C21 N2 H2 112.9(17) . 2_556 ? C21 N2 H2 113.6(17) . . ? C21 N2 H2 112.9(17) 2_556 . ? H2 N2 H2 95(4) . 2_556 ? N1 C11 C12 123.48(18) . . ? N1 C11 C110 115.95(15) . . ? C12 C11 C110 120.57(16) . . ? C11 C12 H12 120.5 . . ? C13 C12 C11 119.02(18) . . ? C13 C12 H12 120.5 . . ? C12 C13 H13 120.1 . . ? C12 C13 C14 119.71(16) . . ? C14 C13 H13 120.1 . . ? C13 C14 C19 117.92(18) . . ? C15 C14 C13 123.12(17) . . ? C15 C14 C19 118.95(17) . . ? C14 C15 H15 119.7 . . ? C16 C15 C14 120.55(18) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 119.9 . . ? C15 C16 C17 120.25(19) . . ? C17 C16 H16 119.9 . . ? C16 C17 H17 119.7 . . ? C18 C17 C16 120.61(18) . . ? C18 C17 H17 119.7 . . ? C17 C18 H18 119.8 . . ? C17 C18 C19 120.44(17) . . ? C19 C18 H18 119.8 . . ? N1 C19 C14 121.20(17) . . ? N1 C19 C18 119.61(16) . . ? C18 C19 C14 119.18(18) . . ? N2 C21 H21A 110.9 . . ? N2 C21 H21B 110.9 . . ? H21A C21 H21B 108.9 . . ? C22 C21 N2 104.3(2) . . ? C22 C21 H21A 110.9 . . ? C22 C21 H21B 110.9 . . ? C21 C22 C22 104.6(2) . 2_556 ? C21 C22 H22A 110.8 . . ? C21 C22 H22B 110.8 . . ? C22 C22 H22A 110.8 2_556 . ? C22 C22 H22B 110.8 2_556 . ? H22A C22 H22B 108.9 . . ? O11 C110 C11 116.99(16) . . ? O12 C110 O11 124.39(19) . . ? O12 C110 C11 118.60(16) . . ? 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 Cl1 2.2670(11) . ? Zn1 O11 1.9976(14) . ? Zn1 O11 1.9976(14) 2_656 ? Zn1 N1 2.2352(15) . ? Zn1 N1 2.2352(15) 2_656 ? O11 C110 1.270(2) . ? O12 C110 1.237(2) . ? N1 C11 1.316(2) . ? N1 C19 1.369(2) . ? N2 C21 1.501(3) 2_556 ? N2 C21 1.501(3) . ? N2 H2 0.88(3) . ? N2 H2 0.88(3) 2_556 ? C11 C12 1.408(3) . ? C11 C110 1.502(3) . ? C12 H12 0.9300 . ? C12 C13 1.354(3) . ? C13 H13 0.9300 . ? C13 C14 1.411(3) . ? C14 C15 1.407(3) . ? C14 C19 1.421(3) . ? C15 H15 0.9300 . ? C15 C16 1.365(3) . ? C16 H16 0.9300 . ? C16 C17 1.408(3) . ? C17 H17 0.9300 . ? C17 C18 1.361(3) . ? C18 H18 0.9300 . ? C18 C19 1.406(3) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C21 C22 1.484(5) . ? C22 C22 1.496(7) 2_556 ? C22 H22A 0.9700 . ? C22 H22B 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 0.88(3) 1.89(3) 2.725(2) 157(3) . 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 -169.19(18) . . . . ? Zn1 O11 C110 C11 12.3(3) . . . . ? Zn1 N1 C11 C12 169.89(18) . . . . ? Zn1 N1 C11 C110 -11.2(2) . . . . ? Zn1 N1 C19 C14 -167.00(16) . . . . ? Zn1 N1 C19 C18 14.2(3) . . . . ? N1 C11 C12 C13 -0.4(4) . . . . ? N1 C11 C110 O11 0.7(3) . . . . ? N1 C11 C110 O12 -177.9(2) . . . . ? N2 C21 C22 C22 -30.2(3) . . . 2_556 ? C11 N1 C19 C14 1.4(3) . . . . ? C11 N1 C19 C18 -177.4(2) . . . . ? C11 C12 C13 C14 1.3(3) . . . . ? C12 C11 C110 O11 179.7(2) . . . . ? C12 C11 C110 O12 1.1(3) . . . . ? C12 C13 C14 C15 178.5(2) . . . . ? C12 C13 C14 C19 -0.9(3) . . . . ? C13 C14 C15 C16 -178.5(2) . . . . ? C13 C14 C19 N1 -0.5(3) . . . . ? C13 C14 C19 C18 178.3(2) . . . . ? C14 C15 C16 C17 0.4(4) . . . . ? C15 C14 C19 N1 -179.9(2) . . . . ? C15 C14 C19 C18 -1.1(3) . . . . ? C15 C16 C17 C18 -1.4(4) . . . . ? C16 C17 C18 C19 1.1(4) . . . . ? C17 C18 C19 N1 179.0(2) . . . . ? C17 C18 C19 C14 0.2(4) . . . . ? C19 N1 C11 C12 -0.9(3) . . . . ? C19 N1 C11 C110 178.0(2) . . . . ? C19 C14 C15 C16 0.8(4) . . . . ? C21 N2 C21 C22 11.58(16) 2_556 . . . ? C110 C11 C12 C13 -179.3(2) . . . . ?