#------------------------------------------------------------------------------ #$Date: 2024-09-29 03:59:32 +0300 (Sun, 29 Sep 2024) $ #$Revision: 294939 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249407.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_7249407 loop_ _publ_author_name 'Gishan, Md' 'Middya, Puspendu' 'Drew, Michael G. B.' 'Frontera, Antonio' 'Chattopadhyay, Shouvik' _publ_section_title ; Synthesis, structural characterization, and theoretical analysis of novel zinc(ii) schiff base complexes with halogen and hydrogen bonding interactions ; _journal_issue 42 _journal_name_full 'RSC Advances' _journal_page_first 30896 _journal_page_last 30911 _journal_paper_doi 10.1039/D4RA06217E _journal_volume 14 _journal_year 2024 _chemical_formula_sum 'C26 H34 N2 O8 Zn' _chemical_formula_weight 567.94 _space_group_crystal_system orthorhombic _space_group_IT_number 41 _space_group_name_Hall 'A 2 -2ab' _space_group_name_H-M_alt 'A e a 2' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2024-04-05 deposited with the CCDC. 2024-09-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 21.494(2) _cell_length_b 13.8469(13) _cell_length_c 9.6418(13) _cell_measurement_reflns_used 900 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 25.152 _cell_measurement_theta_min 2.743 _cell_volume 2869.6(5) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 Quest Area Detector' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_unetI/netI 0.0231 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 24328 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.152 _diffrn_reflns_theta_max 25.152 _diffrn_reflns_theta_min 2.743 _exptl_absorpt_coefficient_mu 0.903 _exptl_absorpt_correction_T_max 0.835 _exptl_absorpt_correction_T_min 0.730 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.315 _exptl_crystal_description block _exptl_crystal_F_000 1192 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.426 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.075 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.36(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 188 _refine_ls_number_reflns 2560 _refine_ls_number_restraints 17 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0500 _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^)+(0.0904P)^2^+3.3038P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1400 _refine_ls_wR_factor_ref 0.1548 _reflns_Friedel_coverage 0.871 _reflns_Friedel_fraction_full 0.993 _reflns_Friedel_fraction_max 0.993 _reflns_number_gt 2091 _reflns_number_total 2572 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ra06217e2.cif _cod_data_source_block shelx_CCDC1 _cod_original_cell_volume 2869.6(6) _cod_original_sg_symbol_Hall 'A 2 -2ac' _cod_original_sg_symbol_H-M 'A b a 2' _cod_database_code 7249407 _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_res_file ; TITL MG 52_b.res in Aba2 shelx.res created by SHELXL-2018/3 at 16:15:58 on 19-Feb-2024 CELL 0.71073 21.4937 13.8469 9.6418 90.000 90.000 90.000 ZERR 4.00 0.0022 0.0013 0.0013 0.000 0.000 0.000 LATT -5 SYMM - X, - Y, Z SYMM 1/2 + X, 1/2 - Y, Z SYMM 1/2 - X, 1/2 + Y, Z SFAC C H N O ZN UNIT 104 168 8 32 4 MERG 2 TWIN dfix 1.45 o2a c2a o2b c2b dfix 1.54 c2b c1b c2a c1a simu c1a c1b simu c2a c2b FMAP 2 PLAN 20 ACTA BOND $H LIST 6 L.S. 24 TEMP 0.00 WGHT 0.090400 3.303800 BASF 0.36257 FVAR 0.50698 0.47359 0.67278 0.46444 0.86411 0.13251 0.14010 FVAR 0.11273 0.01261 -0.06401 -0.03312 ZN1 5 0.500000 0.500000 0.608375 10.50000 0.07980 0.07201 = 0.04290 0.00000 0.00000 -0.00331 N1 3 0.496163 0.370631 0.511986 11.00000 0.07342 0.07522 = 0.04536 -0.00239 0.00200 -0.01703 O1 4 0.573850 0.471745 0.710998 11.00000 0.09695 0.08343 = 0.05566 -0.00784 -0.01871 -0.00498 C3 1 0.668496 0.392539 0.768848 11.00000 0.08012 0.12922 = 0.08032 0.02422 -0.01775 -0.02851 C4 1 0.710277 0.321747 0.749105 11.00000 0.06596 0.16155 = 0.10846 0.03951 -0.02153 -0.01412 AFIX 43 H4 2 0.746268 0.320246 0.802603 11.00000 -1.20000 AFIX 0 C5 1 0.700909 0.254456 0.654955 11.00000 0.05920 0.14094 = 0.17268 0.05122 0.01537 0.00370 AFIX 43 H5 2 0.731079 0.207258 0.641324 11.00000 -1.20000 AFIX 0 C6 1 0.645673 0.252232 0.573493 11.00000 0.06673 0.09665 = 0.11475 0.00522 0.01764 0.00067 AFIX 43 H6 2 0.639310 0.203450 0.508730 11.00000 -1.20000 AFIX 0 C7 1 0.600171 0.326281 0.592989 11.00000 0.06243 0.08057 = 0.06904 0.00740 0.01658 -0.00665 C8 1 0.611459 0.400053 0.689412 11.00000 0.06907 0.08288 = 0.05763 0.01130 -0.00046 -0.01960 C9 1 0.543539 0.312922 0.515695 11.00000 0.07284 0.07033 = 0.04682 -0.00454 0.00823 -0.00641 AFIX 43 H9 2 0.540666 0.256925 0.462825 11.00000 -1.20000 AFIX 0 C10 1 0.439259 0.335542 0.441411 11.00000 0.09493 0.08903 = 0.05236 -0.00094 -0.01144 -0.01003 AFIX 13 H10 2 0.449884 0.279705 0.383622 11.00000 -1.20000 AFIX 0 C11 1 0.391811 0.305096 0.549353 11.00000 0.06767 0.12074 = 0.08028 -0.00087 -0.01257 -0.02918 AFIX 23 H11A 2 0.384662 0.359302 0.611055 11.00000 -1.20000 H11B 2 0.352870 0.291705 0.502284 11.00000 -1.20000 AFIX 0 C12 1 0.408309 0.218853 0.635932 11.00000 0.11055 0.14446 = 0.11611 0.05032 -0.01401 -0.03253 AFIX 33 H12A 2 0.375289 0.205986 0.700384 11.00000 -1.50000 H12B 2 0.414155 0.163781 0.576871 11.00000 -1.50000 H12C 2 0.446043 0.231580 0.685969 11.00000 -1.50000 AFIX 0 C13 1 0.414103 0.415181 0.350023 11.00000 0.10240 0.17390 = 0.06556 0.03088 -0.04048 -0.03481 AFIX 23 H13A 2 0.374306 0.394824 0.312659 11.00000 -1.20000 H13B 2 0.406812 0.471916 0.406751 11.00000 -1.20000 AFIX 0 O1W 4 0.449858 0.437097 -0.037324 11.00000 0.20910 0.12580 = 0.08733 0.03929 -0.00499 -0.02591 PART 1 O2A 4 31.000000 41.000000 51.000000 21.00000 61.00000 71.00000 = 81.00000 91.00000 101.00000 111.00000 C1A 1 0.765520 0.519569 0.933721 21.00000 0.11186 0.12948 = 0.17664 -0.01611 -0.01472 -0.03490 AFIX 33 H1A1 2 0.794323 0.533955 1.006960 21.00000 -1.50000 H1A2 2 0.783673 0.473055 0.871968 21.00000 -1.50000 H1A3 2 0.756154 0.577599 0.883399 21.00000 -1.50000 AFIX 0 C2A 1 0.706404 0.478838 0.994795 21.00000 0.08275 0.15145 = 0.08721 -0.00072 -0.01438 0.00019 AFIX 23 H2A1 2 0.713484 0.418643 1.043773 21.00000 -1.20000 H2A2 2 0.685611 0.524528 1.055350 21.00000 -1.20000 PART 2 AFIX 0 O2B 4 31.000000 41.000000 51.000000 -21.00000 61.00000 71.00000 = 81.00000 91.00000 101.00000 111.00000 C1B 1 0.735928 0.534490 1.032441 -21.00000 0.10407 0.14424 = 0.11955 -0.04720 -0.06950 0.03069 AFIX 33 H1B1 2 0.773457 0.533950 1.086419 -21.00000 -1.50000 H1B2 2 0.734204 0.592648 0.978378 -21.00000 -1.50000 H1B3 2 0.700598 0.531818 1.093235 -21.00000 -1.50000 AFIX 0 C2B 1 0.735184 0.448585 0.937526 -21.00000 0.06810 0.11230 = 0.10449 0.01787 -0.04120 0.01272 AFIX 23 H2B1 2 0.735767 0.388348 0.988864 -21.00000 -1.20000 H2B2 2 0.769725 0.449815 0.872802 -21.00000 -1.20000 PART 0 AFIX 0 O2 4 0.451664 0.439824 0.243897 11.00000 0.24232 0.23274 = 0.06839 0.02478 0.00361 -0.07328 HKLF 4 REM MG 52_b.res in Aba2 REM wR2 = 0.1548, GooF = S = 1.027, Restrained GooF = 1.029 for all data REM R1 = 0.0500 for 2091 Fo > 4sig(Fo) and 0.0646 for all 2560 data REM 188 parameters refined using 17 restraints END WGHT 0.0720 3.2824 REM Highest difference peak 0.426, deepest hole -0.443, 1-sigma level 0.075 Q1 1 0.5000 0.5000 0.3149 10.50000 0.05 0.43 Q2 1 0.5000 0.5000 -0.0729 10.50000 0.05 0.38 Q3 1 0.6854 0.5151 1.1095 11.00000 0.05 0.26 Q4 1 0.4316 0.4999 0.0129 11.00000 0.05 0.26 Q5 1 0.4783 0.4372 0.2307 11.00000 0.05 0.24 Q6 1 0.4378 0.5142 0.0420 11.00000 0.05 0.24 Q7 1 0.4486 0.4964 -0.0812 11.00000 0.05 0.21 Q8 1 0.4522 0.4393 0.1022 11.00000 0.05 0.20 Q9 1 0.4427 0.4315 0.0233 11.00000 0.05 0.20 Q10 1 0.4368 0.5027 0.1828 11.00000 0.05 0.20 Q11 1 0.4387 0.4206 0.1958 11.00000 0.05 0.20 Q12 1 0.5274 0.4327 0.2155 11.00000 0.05 0.20 Q13 1 0.7097 0.6560 1.0128 11.00000 0.05 0.18 Q14 1 0.4364 0.4963 0.3131 11.00000 0.05 0.18 Q15 1 0.4495 0.0725 0.6655 11.00000 0.05 0.18 Q16 1 0.6813 0.2510 0.5977 11.00000 0.05 0.16 Q17 1 0.3201 0.2334 0.6198 11.00000 0.05 0.16 Q18 1 0.3947 0.4803 0.0620 11.00000 0.05 0.16 Q19 1 0.4582 0.1618 0.6714 11.00000 0.05 0.16 Q20 1 0.4536 0.3034 0.2398 11.00000 0.05 0.16 ; _shelx_res_checksum 57246 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, 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 0.6084(2) 0.0649(4) Uani 1 2 d S T P . . N1 N 0.4962(3) 0.3706(5) 0.5120(6) 0.0647(15) Uani 1 1 d . . . . . O1 O 0.5739(3) 0.4717(4) 0.7110(6) 0.0787(14) Uani 1 1 d . . . . . C3 C 0.6685(5) 0.3925(9) 0.7688(11) 0.097(3) Uani 1 1 d . . . . . C4 C 0.7103(5) 0.3217(11) 0.7491(13) 0.112(4) Uani 1 1 d . . . . . H4 H 0.746268 0.320246 0.802603 0.134 Uiso 1 1 calc R U . . . C5 C 0.7009(4) 0.2545(9) 0.6550(17) 0.124(5) Uani 1 1 d . . . . . H5 H 0.731079 0.207258 0.641324 0.149 Uiso 1 1 calc R U . . . C6 C 0.6457(4) 0.2522(7) 0.5735(10) 0.093(3) Uani 1 1 d . . . . . H6 H 0.639310 0.203450 0.508730 0.111 Uiso 1 1 calc R U . . . C7 C 0.6002(3) 0.3263(5) 0.5930(10) 0.0707(19) Uani 1 1 d . . . . . C8 C 0.6115(4) 0.4001(6) 0.6894(7) 0.0699(19) Uani 1 1 d . . . . . C9 C 0.5435(3) 0.3129(5) 0.5157(7) 0.0633(17) Uani 1 1 d . . . . . H9 H 0.540666 0.256925 0.462825 0.076 Uiso 1 1 calc R U . . . C10 C 0.4393(4) 0.3355(6) 0.4414(8) 0.079(2) Uani 1 1 d . . . . . H10 H 0.449884 0.279705 0.383622 0.095 Uiso 1 1 calc R U . . . C11 C 0.3918(4) 0.3051(8) 0.5494(9) 0.090(3) Uani 1 1 d . . . . . H11A H 0.384662 0.359302 0.611055 0.107 Uiso 1 1 calc R U . . . H11B H 0.352870 0.291705 0.502284 0.107 Uiso 1 1 calc R U . . . C12 C 0.4083(5) 0.2189(9) 0.6359(14) 0.124(4) Uani 1 1 d . . . . . H12A H 0.375289 0.205986 0.700384 0.186 Uiso 1 1 calc R U . . . H12B H 0.414155 0.163781 0.576871 0.186 Uiso 1 1 calc R U . . . H12C H 0.446043 0.231580 0.685969 0.186 Uiso 1 1 calc R U . . . C13 C 0.4141(5) 0.4152(10) 0.3500(10) 0.114(4) Uani 1 1 d . . . . . H13A H 0.374306 0.394824 0.312659 0.137 Uiso 1 1 calc R U . . . H13B H 0.406812 0.471916 0.406751 0.137 Uiso 1 1 calc R U . . . O1W O 0.4499(5) 0.4371(6) -0.0373(8) 0.141(4) Uani 1 1 d . . . . . O2A O 0.6728(4) 0.4644(7) 0.8641(10) 0.128(3) Uani 0.47(3) 1 d D . P A 1 C1A C 0.7655(14) 0.520(3) 0.934(4) 0.139(13) Uani 0.47(3) 1 d D U P A 1 H1A1 H 0.794323 0.533955 1.006960 0.209 Uiso 0.47(3) 1 calc R U P A 1 H1A2 H 0.783673 0.473055 0.871968 0.209 Uiso 0.47(3) 1 calc R U P A 1 H1A3 H 0.756154 0.577599 0.883399 0.209 Uiso 0.47(3) 1 calc R U P A 1 C2A C 0.7064(13) 0.479(3) 0.995(2) 0.107(9) Uani 0.47(3) 1 d D U P A 1 H2A1 H 0.713484 0.418643 1.043773 0.129 Uiso 0.47(3) 1 calc R U P A 1 H2A2 H 0.685611 0.524528 1.055350 0.129 Uiso 0.47(3) 1 calc R U P A 1 O2B O 0.6728(4) 0.4644(7) 0.8641(10) 0.128(3) Uani 0.53(3) 1 d D . P A 2 C1B C 0.7359(15) 0.534(2) 1.032(3) 0.123(11) Uani 0.53(3) 1 d D U P A 2 H1B1 H 0.773457 0.533950 1.086419 0.184 Uiso 0.53(3) 1 calc R U P A 2 H1B2 H 0.734204 0.592648 0.978378 0.184 Uiso 0.53(3) 1 calc R U P A 2 H1B3 H 0.700598 0.531818 1.093235 0.184 Uiso 0.53(3) 1 calc R U P A 2 C2B C 0.7352(11) 0.4486(15) 0.938(3) 0.095(7) Uani 0.53(3) 1 d D U P A 2 H2B1 H 0.735767 0.388348 0.988864 0.114 Uiso 0.53(3) 1 calc R U P A 2 H2B2 H 0.769725 0.449815 0.872802 0.114 Uiso 0.53(3) 1 calc R U P A 2 O2 O 0.4517(6) 0.4398(11) 0.2439(9) 0.181(6) 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 0.0798(7) 0.0720(6) 0.0429(5) 0.000 0.000 -0.0033(6) N1 0.073(4) 0.075(4) 0.045(3) -0.002(3) 0.002(3) -0.017(3) O1 0.097(4) 0.083(3) 0.056(3) -0.008(3) -0.019(3) -0.005(3) C3 0.080(6) 0.129(8) 0.080(5) 0.024(6) -0.018(5) -0.029(6) C4 0.066(6) 0.162(11) 0.108(8) 0.040(8) -0.022(6) -0.014(7) C5 0.059(5) 0.141(10) 0.173(13) 0.051(9) 0.015(7) 0.004(6) C6 0.067(5) 0.097(6) 0.115(8) 0.005(5) 0.018(5) 0.001(4) C7 0.062(4) 0.081(4) 0.069(5) 0.007(4) 0.017(4) -0.007(3) C8 0.069(4) 0.083(5) 0.058(4) 0.011(4) 0.000(3) -0.020(4) C9 0.073(5) 0.070(4) 0.047(3) -0.005(3) 0.008(3) -0.006(4) C10 0.095(6) 0.089(5) 0.052(4) -0.001(4) -0.011(4) -0.010(4) C11 0.068(5) 0.121(7) 0.080(5) -0.001(5) -0.013(4) -0.029(5) C12 0.111(7) 0.144(9) 0.116(9) 0.050(8) -0.014(7) -0.033(7) C13 0.102(7) 0.174(11) 0.066(5) 0.031(6) -0.040(5) -0.035(7) O1W 0.209(12) 0.126(7) 0.087(6) 0.039(5) -0.005(6) -0.026(6) O2A 0.133(6) 0.140(5) 0.113(5) 0.013(6) -0.064(5) -0.033(6) C1A 0.11(2) 0.13(2) 0.18(4) -0.02(2) -0.01(2) -0.035(18) C2A 0.083(16) 0.15(2) 0.087(16) -0.001(16) -0.014(14) 0.000(16) O2B 0.133(6) 0.140(5) 0.113(5) 0.013(6) -0.064(5) -0.033(6) C1B 0.104(19) 0.144(18) 0.12(2) -0.047(16) -0.069(16) 0.031(15) C2B 0.068(14) 0.112(15) 0.104(15) 0.018(12) -0.041(12) 0.013(11) O2 0.242(15) 0.233(14) 0.068(6) 0.025(7) 0.004(7) -0.073(11) 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 O1 Zn1 O1 117.6(4) . 2_665 ? O1 Zn1 N1 95.2(3) . . ? O1 Zn1 N1 112.7(2) 2_665 . ? O1 Zn1 N1 112.7(2) . 2_665 ? O1 Zn1 N1 95.2(3) 2_665 2_665 ? N1 Zn1 N1 125.2(4) . 2_665 ? C9 N1 C10 117.4(7) . . ? C9 N1 Zn1 120.2(5) . . ? C10 N1 Zn1 122.4(5) . . ? C8 O1 Zn1 126.2(5) . . ? C4 C3 O2B 125.9(10) . . ? C4 C3 O2A 125.9(10) . . ? C4 C3 C8 122.9(10) . . ? O2B C3 C8 111.2(10) . . ? O2A C3 C8 111.2(10) . . ? C5 C4 C3 120.8(10) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.6(11) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C7 118.8(10) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C8 C7 C6 119.4(8) . . ? C8 C7 C9 125.7(7) . . ? C6 C7 C9 114.7(8) . . ? O1 C8 C7 123.8(7) . . ? O1 C8 C3 119.8(8) . . ? C7 C8 C3 116.4(9) . . ? N1 C9 C7 126.9(7) . . ? N1 C9 H9 116.6 . . ? C7 C9 H9 116.6 . . ? N1 C10 C13 108.9(7) . . ? N1 C10 C11 109.3(6) . . ? C13 C10 C11 111.2(8) . . ? N1 C10 H10 109.1 . . ? C13 C10 H10 109.1 . . ? C11 C10 H10 109.1 . . ? C12 C11 C10 116.4(9) . . ? C12 C11 H11A 108.2 . . ? C10 C11 H11A 108.2 . . ? C12 C11 H11B 108.2 . . ? C10 C11 H11B 108.2 . . ? H11A C11 H11B 107.3 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 C10 114.4(11) . . ? O2 C13 H13A 108.7 . . ? C10 C13 H13A 108.7 . . ? O2 C13 H13B 108.7 . . ? C10 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C3 O2A C2A 135.6(18) . . ? C2A C1A H1A1 109.5 . . ? C2A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C2A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? O2A C2A C1A 97(2) . . ? O2A C2A H2A1 112.3 . . ? C1A C2A H2A1 112.3 . . ? O2A C2A H2A2 112.3 . . ? C1A C2A H2A2 112.3 . . ? H2A1 C2A H2A2 109.9 . . ? C3 O2B C2B 105.5(12) . . ? C2B C1B H1B1 109.5 . . ? C2B C1B H1B2 109.5 . . ? H1B1 C1B H1B2 109.5 . . ? C2B C1B H1B3 109.5 . . ? H1B1 C1B H1B3 109.5 . . ? H1B2 C1B H1B3 109.5 . . ? C1B C2B O2B 100.2(16) . . ? C1B C2B H2B1 111.7 . . ? O2B C2B H2B1 111.7 . . ? C1B C2B H2B2 111.7 . . ? O2B C2B H2B2 111.7 . . ? H2B1 C2B H2B2 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 O1 1.911(6) . ? Zn1 O1 1.911(6) 2_665 ? Zn1 N1 2.020(7) . ? Zn1 N1 2.020(7) 2_665 ? N1 C9 1.295(9) . ? N1 C10 1.482(10) . ? O1 C8 1.297(10) . ? C3 C4 1.343(16) . ? C3 O2B 1.358(14) . ? C3 O2A 1.358(14) . ? C3 C8 1.449(12) . ? C4 C5 1.316(17) . ? C4 H4 0.9300 . ? C5 C6 1.424(15) . ? C5 H5 0.9300 . ? C6 C7 1.429(11) . ? C6 H6 0.9300 . ? C7 C8 1.402(11) . ? C7 C9 1.439(11) . ? C9 H9 0.9300 . ? C10 C13 1.512(13) . ? C10 C11 1.517(11) . ? C10 H10 0.9800 . ? C11 C12 1.500(14) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O2 1.347(14) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? O2A C2A 1.47(2) . ? C1A C2A 1.51(3) . ? C1A H1A1 0.9600 . ? C1A H1A2 0.9600 . ? C1A H1A3 0.9600 . ? C2A H2A1 0.9700 . ? C2A H2A2 0.9700 . ? O2B C2B 1.532(16) . ? C1B C2B 1.50(2) . ? C1B H1B1 0.9600 . ? C1B H1B2 0.9600 . ? C1B H1B3 0.9600 . ? C2B H2B1 0.9700 . ? C2B H2B2 0.9700 . ?