#------------------------------------------------------------------------------ #$Date: 2024-09-29 03:59:32 +0300 (Sun, 29 Sep 2024) $ #$Revision: 294939 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249408.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_7249408 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 'C22 H26 Br2 N2 O4 Zn' _chemical_formula_weight 607.64 _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_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 108.1730(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5138(5) _cell_length_b 11.9667(4) _cell_length_c 16.7858(7) _cell_measurement_reflns_used 900 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 27.133 _cell_measurement_theta_min 2.128 _cell_volume 2388.27(16) _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 0.988 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'BRUKER D8 QUEST AREA DETECTOR' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0799 _diffrn_reflns_av_unetI/netI 0.0537 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 33326 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.133 _diffrn_reflns_theta_min 2.128 _exptl_absorpt_coefficient_mu 4.405 _exptl_absorpt_correction_T_max 0.414 _exptl_absorpt_correction_T_min 0.223 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.690 _exptl_crystal_description niddle _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 2.127 _refine_diff_density_min -1.032 _refine_diff_density_rms 0.251 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 5297 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0682 _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^)+(0.1490P)^2^+2.1239P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1997 _refine_ls_wR_factor_ref 0.2263 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3785 _reflns_number_total 5297 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ra06217e2.cif _cod_data_source_block shelx_CCDC2 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7249408 _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 SC_MG_6_a.res in P2(1)/n shelx.res created by SHELXL-2018/3 at 15:55:45 on 22-Sep-2023 CELL 0.71073 12.5138 11.9667 16.7858 90.000 108.173 90.000 ZERR 4.00 0.0005 0.0004 0.0007 0.000 0.001 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H O ZN BR N UNIT 92 92 24 4 8 0 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H CONF L.S. 100 TEMP 0.00 WGHT 0.149000 2.123900 FVAR 0.35181 0.89408 C22 1 0.514676 0.460060 0.604969 11.00000 0.05687 0.11514 = 0.05127 -0.01859 0.02176 -0.01837 AFIX 23 H22A 2 0.463839 0.410643 0.564837 11.00000 -1.20000 H22B 2 0.491142 0.536321 0.589218 11.00000 -1.20000 AFIX 0 C11 1 0.888982 0.331442 0.702668 11.00000 0.09767 0.04170 = 0.09383 0.01357 0.05391 0.01432 AFIX 23 H11A 2 0.852338 0.301593 0.647107 11.00000 -1.20000 H11B 2 0.939514 0.274573 0.734777 11.00000 -1.20000 AFIX 0 BR1 5 0.800129 0.878179 0.361952 11.00000 0.07466 0.08411 = 0.06685 0.04518 0.04272 0.02523 BR2 5 0.653610 0.717300 1.115843 11.00000 0.11857 0.11146 = 0.05031 -0.02337 0.04345 0.01604 ZN1 4 0.745721 0.535011 0.719728 11.00000 0.04593 0.03656 = 0.03602 -0.00128 0.02470 -0.00254 N1 6 0.871319 0.523235 0.663698 11.00000 0.04200 0.03052 = 0.03563 0.00069 0.02200 0.00150 O1 3 0.693847 0.683383 0.658440 11.00000 0.05351 0.04587 = 0.04644 0.00917 0.03409 0.01259 O2 3 0.809316 0.354724 0.740584 11.00000 0.06782 0.03927 = 0.06591 0.01148 0.04084 0.00375 AFIX 43 H2W 2 0.783697 0.302722 0.771585 11.00000 -1.20000 AFIX 0 N2 6 0.601918 0.497153 0.753079 11.00000 0.03882 0.03317 = 0.03101 0.00031 0.01452 -0.00129 O3 3 0.825384 0.589649 0.832473 11.00000 0.04609 0.05984 = 0.04100 -0.00985 0.02441 -0.00859 C4 1 0.767328 0.816898 0.455353 11.00000 0.04734 0.04439 = 0.04016 0.01090 0.02001 0.00340 C3 1 0.683466 0.862878 0.483728 11.00000 0.04114 0.04154 = 0.03998 0.00414 0.01022 0.00667 AFIX 43 H3 2 0.642306 0.924152 0.456508 11.00000 -1.20000 AFIX 0 C2 1 0.662191 0.817159 0.551928 11.00000 0.04262 0.03929 = 0.03860 -0.00087 0.01633 0.00798 AFIX 43 H2 2 0.607508 0.850282 0.571021 11.00000 -1.20000 AFIX 0 C1 1 0.719031 0.722158 0.594892 11.00000 0.03546 0.03621 = 0.02798 -0.00232 0.01538 -0.00208 C6 1 0.804543 0.677569 0.565834 11.00000 0.04361 0.03445 = 0.03466 0.00379 0.02199 0.00492 C7 1 0.877261 0.586180 0.603882 11.00000 0.04679 0.03643 = 0.04354 0.00378 0.02812 0.00451 AFIX 43 H7 2 0.935710 0.571158 0.582245 11.00000 -1.20000 AFIX 0 C8 1 0.956593 0.433547 0.695317 11.00000 0.04363 0.03382 = 0.05791 0.00940 0.02718 0.00799 C9 1 1.027791 0.405880 0.641077 11.00000 0.15794 0.11264 = 0.16708 0.08724 0.13814 0.09705 AFIX 33 H9A 2 1.079640 0.347490 0.666890 11.00000 -1.50000 H9B 2 0.980561 0.381307 0.587144 11.00000 -1.50000 H9C 2 1.068857 0.471091 0.634393 11.00000 -1.50000 AFIX 0 C10 1 1.027298 0.468078 0.782621 11.00000 0.06318 0.08950 = 0.09560 0.00825 -0.01141 0.01110 AFIX 33 H10A 2 1.083708 0.412360 0.805563 11.00000 -1.50000 H10B 2 1.062944 0.538389 0.779918 11.00000 -1.50000 H10C 2 0.980075 0.475379 0.817737 11.00000 -1.50000 AFIX 0 C19 1 0.506214 0.436790 0.691856 11.00000 0.04038 0.04938 = 0.03801 -0.00472 0.01314 -0.00643 C21 1 0.519710 0.311453 0.714231 11.00000 0.07677 0.05067 = 0.08060 -0.01118 0.01835 -0.01693 AFIX 33 H21A 2 0.459456 0.270235 0.676015 11.00000 -1.50000 H21B 2 0.590333 0.285267 0.710156 11.00000 -1.50000 H21C 2 0.517740 0.300855 0.770446 11.00000 -1.50000 AFIX 0 C20 1 0.392131 0.477719 0.693528 11.00000 0.04747 0.09704 = 0.06985 -0.02270 0.01378 -0.00024 AFIX 33 H20A 2 0.333927 0.436555 0.653349 11.00000 -1.50000 H20B 2 0.385832 0.466701 0.748536 11.00000 -1.50000 H20C 2 0.384479 0.555789 0.679756 11.00000 -1.50000 AFIX 0 C18 1 0.594369 0.519228 0.825131 11.00000 0.04196 0.03833 = 0.03344 0.00213 0.01847 -0.00249 AFIX 43 H18 2 0.529565 0.494686 0.835686 11.00000 -1.20000 AFIX 0 C17 1 0.675940 0.578752 0.893168 11.00000 0.04761 0.03401 = 0.02873 0.00407 0.01548 0.00053 C12 1 0.784558 0.611009 0.892150 11.00000 0.04541 0.03397 = 0.02955 0.00259 0.00765 0.00437 C13 1 0.850538 0.672208 0.962260 11.00000 0.04813 0.04735 = 0.04049 -0.00141 0.00364 -0.00251 AFIX 43 H13 2 0.922882 0.692988 0.964102 11.00000 -1.20000 AFIX 0 C14 1 0.813499 0.702004 1.026815 11.00000 0.06718 0.06151 = 0.03279 -0.00840 0.00683 -0.00330 AFIX 43 H14 2 0.859337 0.743344 1.071338 11.00000 -1.20000 AFIX 0 C15 1 0.706028 0.670202 1.026016 11.00000 0.07588 0.06014 = 0.02918 -0.00363 0.02289 0.00873 C16 1 0.639982 0.609003 0.961777 11.00000 0.05681 0.05205 = 0.03200 0.00073 0.02052 0.00507 AFIX 43 H16 2 0.569359 0.586409 0.962901 11.00000 -1.20000 AFIX 0 C5 1 0.826754 0.726805 0.496289 11.00000 0.05120 0.04537 = 0.04694 0.01398 0.03001 0.01280 AFIX 43 H5 2 0.883479 0.697111 0.477743 11.00000 -1.20000 AFIX 0 O4 3 0.624446 0.444791 0.601197 11.00000 0.08700 0.09970 = 0.05960 -0.01813 0.03728 -0.01089 AFIX 43 H4 2 0.645059 0.406589 0.560003 11.00000 -1.20000 AFIX 0 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM SC_MG_6_a.res in P2(1)/n REM wR2 = 0.2263, GooF = S = 1.037, Restrained GooF = 1.037 for all data REM R1 = 0.0682 for 3785 Fo > 4sig(Fo) and 0.0949 for all 5206 data REM 281 parameters refined using 0 restraints END WGHT 0.1474 2.0634 REM Highest difference peak 2.127, deepest hole -1.032, 1-sigma level 0.251 Q1 1 0.4870 0.5605 0.5723 11.00000 0.05 2.13 Q2 1 0.9359 0.3709 0.7647 11.00000 0.05 1.21 Q3 1 1.0734 0.4821 0.7166 11.00000 0.05 1.07 Q4 1 0.9266 0.3473 0.6082 11.00000 0.05 1.00 Q5 1 0.5534 0.3687 0.6305 11.00000 0.05 0.92 Q6 1 0.4557 0.3642 0.7363 11.00000 0.05 0.73 Q7 1 0.4589 0.2851 0.6394 11.00000 0.05 0.69 Q8 1 0.4416 0.5452 0.6265 11.00000 0.05 0.68 Q9 1 0.5134 0.4728 0.9151 11.00000 0.05 0.65 Q10 1 0.9444 0.3639 0.8198 11.00000 0.05 0.63 Q11 1 0.4197 0.4654 0.8520 11.00000 0.05 0.62 Q12 1 0.5442 0.5307 0.7233 11.00000 0.05 0.62 Q13 1 0.6460 0.7829 1.0841 11.00000 0.05 0.62 Q14 1 0.7025 0.5349 0.7585 11.00000 0.05 0.61 Q15 1 0.9856 0.7503 0.9209 11.00000 0.05 0.60 Q16 1 1.0070 0.7277 1.0189 11.00000 0.05 0.60 Q17 1 0.4559 0.4499 0.8781 11.00000 0.05 0.59 Q18 1 1.0210 0.5427 0.6376 11.00000 0.05 0.58 Q19 1 1.0185 0.6937 0.9496 11.00000 0.05 0.58 Q20 1 0.9947 0.5810 0.5864 11.00000 0.05 0.57 ; _shelx_res_checksum 10472 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 C22 C 0.5147(6) 0.4601(8) 0.6050(5) 0.073(2) Uani 1 1 d . . . . . H22A H 0.463839 0.410643 0.564837 0.088 Uiso 1 1 calc R U . . . H22B H 0.491142 0.536321 0.589218 0.088 Uiso 1 1 calc R U . . . C11 C 0.8890(8) 0.3314(6) 0.7027(6) 0.072(2) Uani 1 1 d . . . . . H11A H 0.852338 0.301593 0.647107 0.087 Uiso 1 1 calc R U . . . H11B H 0.939514 0.274573 0.734777 0.087 Uiso 1 1 calc R U . . . Br1 Br 0.80013(7) 0.87818(7) 0.36195(5) 0.0704(3) Uani 1 1 d . . . . . Br2 Br 0.65361(9) 0.71730(9) 1.11584(5) 0.0895(4) Uani 1 1 d . . . . . Zn1 Zn 0.74572(5) 0.53501(5) 0.71973(4) 0.0368(2) Uani 1 1 d . . . . . N1 N 0.8713(4) 0.5232(3) 0.6637(3) 0.0338(9) Uani 1 1 d . . . . . O1 O 0.6938(3) 0.6834(3) 0.6584(3) 0.0443(9) Uani 1 1 d . . . . . O2 O 0.8093(4) 0.3547(3) 0.7406(3) 0.0531(11) Uani 1 1 d . . . . . H2W H 0.783697 0.302722 0.771585 0.064 Uiso 1 1 calc R U . . . N2 N 0.6019(4) 0.4972(4) 0.7531(3) 0.0335(9) Uani 1 1 d . . . . . O3 O 0.8254(3) 0.5896(4) 0.8325(3) 0.0465(10) Uani 1 1 d . . . . . C4 C 0.7673(5) 0.8169(5) 0.4554(4) 0.0425(13) Uani 1 1 d . . . . . C3 C 0.6835(5) 0.8629(5) 0.4837(4) 0.0414(13) Uani 1 1 d . . . . . H3 H 0.642306 0.924152 0.456508 0.050 Uiso 1 1 calc R U . . . C2 C 0.6622(5) 0.8172(5) 0.5519(3) 0.0393(12) Uani 1 1 d . . . . . H2 H 0.607508 0.850282 0.571021 0.047 Uiso 1 1 calc R U . . . C1 C 0.7190(4) 0.7222(4) 0.5949(3) 0.0320(10) Uani 1 1 d . . . . . C6 C 0.8045(5) 0.6776(4) 0.5658(3) 0.0353(11) Uani 1 1 d . . . . . C7 C 0.8773(5) 0.5862(4) 0.6039(4) 0.0390(12) Uani 1 1 d . . . . . H7 H 0.935710 0.571158 0.582245 0.047 Uiso 1 1 calc R U . . . C8 C 0.9566(5) 0.4335(5) 0.6953(4) 0.0425(13) Uani 1 1 d . . . . . C9 C 1.0278(10) 0.4059(9) 0.6411(8) 0.126(5) Uani 1 1 d . . . . . H9A H 1.079640 0.347490 0.666890 0.189 Uiso 1 1 calc R U . . . H9B H 0.980561 0.381307 0.587144 0.189 Uiso 1 1 calc R U . . . H9C H 1.068857 0.471091 0.634393 0.189 Uiso 1 1 calc R U . . . C10 C 1.0273(7) 0.4681(8) 0.7826(6) 0.091(3) Uani 1 1 d . . . . . H10A H 1.083708 0.412360 0.805563 0.137 Uiso 1 1 calc R U . . . H10B H 1.062944 0.538389 0.779918 0.137 Uiso 1 1 calc R U . . . H10C H 0.980075 0.475379 0.817737 0.137 Uiso 1 1 calc R U . . . C19 C 0.5062(5) 0.4368(5) 0.6919(4) 0.0424(13) Uani 1 1 d . . . . . C21 C 0.5197(7) 0.3115(6) 0.7142(5) 0.071(2) Uani 1 1 d . . . . . H21A H 0.459456 0.270235 0.676015 0.106 Uiso 1 1 calc R U . . . H21B H 0.590333 0.285267 0.710156 0.106 Uiso 1 1 calc R U . . . H21C H 0.517740 0.300855 0.770446 0.106 Uiso 1 1 calc R U . . . C20 C 0.3921(6) 0.4777(7) 0.6935(5) 0.072(2) Uani 1 1 d . . . . . H20A H 0.333927 0.436555 0.653349 0.109 Uiso 1 1 calc R U . . . H20B H 0.385832 0.466701 0.748536 0.109 Uiso 1 1 calc R U . . . H20C H 0.384479 0.555789 0.679756 0.109 Uiso 1 1 calc R U . . . C18 C 0.5944(5) 0.5192(4) 0.8251(3) 0.0364(11) Uani 1 1 d . . . . . H18 H 0.529565 0.494686 0.835686 0.044 Uiso 1 1 calc R U . . . C17 C 0.6759(5) 0.5788(4) 0.8932(3) 0.0360(11) Uani 1 1 d . . . . . C12 C 0.7846(5) 0.6110(4) 0.8921(3) 0.0372(12) Uani 1 1 d . . . . . C13 C 0.8505(5) 0.6722(5) 0.9623(4) 0.0477(15) Uani 1 1 d . . . . . H13 H 0.922882 0.692988 0.964102 0.057 Uiso 1 1 calc R U . . . C14 C 0.8135(6) 0.7020(6) 1.0268(4) 0.0558(17) Uani 1 1 d . . . . . H14 H 0.859337 0.743344 1.071338 0.067 Uiso 1 1 calc R U . . . C15 C 0.7060(6) 0.6702(6) 1.0260(4) 0.0536(16) Uani 1 1 d . . . . . C16 C 0.6400(6) 0.6090(5) 0.9618(4) 0.0454(14) Uani 1 1 d . . . . . H16 H 0.569359 0.586409 0.962901 0.054 Uiso 1 1 calc R U . . . C5 C 0.8268(5) 0.7268(5) 0.4963(4) 0.0445(13) Uani 1 1 d . . . . . H5 H 0.883479 0.697111 0.477743 0.053 Uiso 1 1 calc R U . . . O4 O 0.6244(5) 0.4448(5) 0.6012(4) 0.0788(16) Uani 1 1 d . . . . . H4 H 0.645059 0.406589 0.560003 0.095 Uiso 1 1 calc R U . . . 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 C22 0.057(4) 0.115(7) 0.051(4) -0.019(4) 0.022(3) -0.018(4) C11 0.098(6) 0.042(4) 0.094(6) 0.014(4) 0.054(5) 0.014(4) Br1 0.0747(5) 0.0841(6) 0.0669(5) 0.0452(4) 0.0427(4) 0.0252(4) Br2 0.1186(8) 0.1115(8) 0.0503(5) -0.0234(5) 0.0435(5) 0.0160(6) Zn1 0.0459(4) 0.0366(4) 0.0360(4) -0.0013(2) 0.0247(3) -0.0025(3) N1 0.042(2) 0.031(2) 0.036(2) 0.0007(18) 0.0220(19) 0.0015(17) O1 0.054(2) 0.046(2) 0.046(2) 0.0092(18) 0.0341(19) 0.0126(18) O2 0.068(3) 0.039(2) 0.066(3) 0.011(2) 0.041(2) 0.0038(19) N2 0.039(2) 0.033(2) 0.031(2) 0.0003(18) 0.0145(18) -0.0013(18) O3 0.046(2) 0.060(3) 0.041(2) -0.0099(19) 0.0244(18) -0.0086(19) C4 0.047(3) 0.044(3) 0.040(3) 0.011(3) 0.020(2) 0.003(2) C3 0.041(3) 0.042(3) 0.040(3) 0.004(2) 0.010(2) 0.007(2) C2 0.043(3) 0.039(3) 0.039(3) -0.001(2) 0.016(2) 0.008(2) C1 0.035(3) 0.036(3) 0.028(2) -0.002(2) 0.015(2) -0.002(2) C6 0.044(3) 0.034(3) 0.035(3) 0.004(2) 0.022(2) 0.005(2) C7 0.047(3) 0.036(3) 0.044(3) 0.004(2) 0.028(3) 0.005(2) C8 0.044(3) 0.034(3) 0.058(4) 0.009(3) 0.027(3) 0.008(2) C9 0.158(10) 0.113(8) 0.167(11) 0.087(8) 0.138(9) 0.097(7) C10 0.063(5) 0.089(6) 0.096(7) 0.008(5) -0.011(5) 0.011(4) C19 0.040(3) 0.049(3) 0.038(3) -0.005(2) 0.013(2) -0.006(2) C21 0.077(5) 0.051(4) 0.081(5) -0.011(4) 0.018(4) -0.017(4) C20 0.047(4) 0.097(6) 0.070(5) -0.023(4) 0.014(4) 0.000(4) C18 0.042(3) 0.038(3) 0.033(3) 0.002(2) 0.018(2) -0.002(2) C17 0.048(3) 0.034(2) 0.029(2) 0.004(2) 0.015(2) 0.001(2) C12 0.045(3) 0.034(3) 0.030(2) 0.003(2) 0.008(2) 0.004(2) C13 0.048(3) 0.047(3) 0.040(3) -0.001(3) 0.004(3) -0.003(3) C14 0.067(4) 0.062(4) 0.033(3) -0.008(3) 0.007(3) -0.003(3) C15 0.076(4) 0.060(4) 0.029(3) -0.004(3) 0.023(3) 0.009(3) C16 0.057(4) 0.052(3) 0.032(3) 0.001(2) 0.021(3) 0.005(3) C5 0.051(3) 0.045(3) 0.047(3) 0.014(3) 0.030(3) 0.013(3) O4 0.087(4) 0.100(4) 0.060(3) -0.018(3) 0.037(3) -0.011(3) 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' 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' Br Br -0.2901 2.4595 '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' 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 O4 C22 C19 112.4(6) . . ? O4 C22 H22A 109.1 . . ? C19 C22 H22A 109.1 . . ? O4 C22 H22B 109.1 . . ? C19 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? O2 C11 C8 112.4(6) . . ? O2 C11 H11A 109.1 . . ? C8 C11 H11A 109.1 . . ? O2 C11 H11B 109.1 . . ? C8 C11 H11B 109.1 . . ? H11A C11 H11B 107.9 . . ? O3 Zn1 O1 100.48(18) . . ? O3 Zn1 N1 103.41(17) . . ? O1 Zn1 N1 89.85(16) . . ? O3 Zn1 N2 91.99(17) . . ? O1 Zn1 N2 99.05(16) . . ? N1 Zn1 N2 160.56(17) . . ? O3 Zn1 O2 96.84(18) . . ? O1 Zn1 O2 158.82(16) . . ? N1 Zn1 O2 74.25(16) . . ? N2 Zn1 O2 92.41(17) . . ? O3 Zn1 O4 166.1(2) . . ? O1 Zn1 O4 87.3(2) . . ? N1 Zn1 O4 88.02(19) . . ? N2 Zn1 O4 75.26(19) . . ? O2 Zn1 O4 78.4(2) . . ? C7 N1 C8 119.6(5) . . ? C7 N1 Zn1 123.7(4) . . ? C8 N1 Zn1 116.6(3) . . ? C1 O1 Zn1 127.2(3) . . ? C11 O2 Zn1 112.9(4) . . ? C11 O2 H2W 123.5 . . ? Zn1 O2 H2W 123.5 . . ? C18 N2 C19 118.2(5) . . ? C18 N2 Zn1 122.3(4) . . ? C19 N2 Zn1 119.4(3) . . ? C12 O3 Zn1 127.9(4) . . ? C5 C4 C3 119.3(5) . . ? C5 C4 Br1 119.9(4) . . ? C3 C4 Br1 120.8(4) . . ? C2 C3 C4 119.5(5) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C2 C1 123.4(5) . . ? C3 C2 H2 118.3 . . ? C1 C2 H2 118.3 . . ? O1 C1 C6 123.8(5) . . ? O1 C1 C2 119.8(5) . . ? C6 C1 C2 116.3(5) . . ? C1 C6 C5 119.6(5) . . ? C1 C6 C7 125.2(5) . . ? C5 C6 C7 115.1(5) . . ? N1 C7 C6 127.9(5) . . ? N1 C7 H7 116.1 . . ? C6 C7 H7 116.1 . . ? N1 C8 C9 116.0(6) . . ? N1 C8 C11 104.7(5) . . ? C9 C8 C11 109.0(7) . . ? N1 C8 C10 106.6(5) . . ? C9 C8 C10 111.7(8) . . ? C11 C8 C10 108.3(7) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C19 C20 112.8(5) . . ? N2 C19 C22 106.8(5) . . ? C20 C19 C22 107.8(6) . . ? N2 C19 C21 107.4(5) . . ? C20 C19 C21 110.0(6) . . ? C22 C19 C21 112.1(6) . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N2 C18 C17 127.3(5) . . ? N2 C18 H18 116.4 . . ? C17 C18 H18 116.4 . . ? C16 C17 C12 119.5(5) . . ? C16 C17 C18 116.2(5) . . ? C12 C17 C18 124.3(5) . . ? O3 C12 C13 118.8(5) . . ? O3 C12 C17 124.8(5) . . ? C13 C12 C17 116.4(5) . . ? C14 C13 C12 123.1(6) . . ? C14 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? C13 C14 C15 119.4(6) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.3(6) . . ? C16 C15 Br2 121.0(6) . . ? C14 C15 Br2 118.7(5) . . ? C15 C16 C17 121.3(6) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C4 C5 C6 121.9(5) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C22 O4 Zn1 106.5(4) . . ? C22 O4 H4 126.8 . . ? Zn1 O4 H4 126.8 . . ? 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 C22 O4 1.407(9) . ? C22 C19 1.521(10) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C11 O2 1.368(9) . ? C11 C8 1.513(9) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? Br1 C4 1.888(6) . ? Br2 C15 1.907(6) . ? Zn1 O3 1.956(4) . ? Zn1 O1 2.053(4) . ? Zn1 N1 2.073(4) . ? Zn1 N2 2.094(4) . ? Zn1 O2 2.288(4) . ? Zn1 O4 2.355(6) . ? N1 C7 1.276(7) . ? N1 C8 1.490(7) . ? O1 C1 1.289(6) . ? O2 H2W 0.9300 . ? N2 C18 1.270(7) . ? N2 C19 1.498(7) . ? O3 C12 1.284(7) . ? C4 C5 1.367(8) . ? C4 C3 1.394(8) . ? C3 C2 1.368(8) . ? C3 H3 0.9300 . ? C2 C1 1.414(7) . ? C2 H2 0.9300 . ? C1 C6 1.412(7) . ? C6 C5 1.411(8) . ? C6 C7 1.439(7) . ? C7 H7 0.9300 . ? C8 C9 1.496(10) . ? C8 C10 1.514(10) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C19 C20 1.518(9) . ? C19 C21 1.543(9) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C18 C17 1.458(8) . ? C18 H18 0.9300 . ? C17 C16 1.408(8) . ? C17 C12 1.418(8) . ? C12 C13 1.413(8) . ? C13 C14 1.353(9) . ? C13 H13 0.9300 . ? C14 C15 1.394(10) . ? C14 H14 0.9300 . ? C15 C16 1.351(9) . ? C16 H16 0.9300 . ? C5 H5 0.9300 . ? O4 H4 0.9300 . ? 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 C8 C11 O2 Zn1 28.9(8) . . . . ? C5 C4 C3 C2 0.0(9) . . . . ? Br1 C4 C3 C2 -179.5(4) . . . . ? C4 C3 C2 C1 -1.9(9) . . . . ? Zn1 O1 C1 C6 -12.3(7) . . . . ? Zn1 O1 C1 C2 170.0(4) . . . . ? C3 C2 C1 O1 -179.6(5) . . . . ? C3 C2 C1 C6 2.6(8) . . . . ? O1 C1 C6 C5 -179.2(5) . . . . ? C2 C1 C6 C5 -1.4(8) . . . . ? O1 C1 C6 C7 -2.1(9) . . . . ? C2 C1 C6 C7 175.7(5) . . . . ? C8 N1 C7 C6 -179.0(5) . . . . ? Zn1 N1 C7 C6 2.5(8) . . . . ? C1 C6 C7 N1 7.4(10) . . . . ? C5 C6 C7 N1 -175.4(6) . . . . ? C7 N1 C8 C9 -14.1(10) . . . . ? Zn1 N1 C8 C9 164.5(7) . . . . ? C7 N1 C8 C11 -134.3(6) . . . . ? Zn1 N1 C8 C11 44.4(6) . . . . ? C7 N1 C8 C10 111.1(7) . . . . ? Zn1 N1 C8 C10 -70.3(6) . . . . ? O2 C11 C8 N1 -45.9(8) . . . . ? O2 C11 C8 C9 -170.7(8) . . . . ? O2 C11 C8 C10 67.6(8) . . . . ? C18 N2 C19 C20 40.6(8) . . . . ? Zn1 N2 C19 C20 -142.4(5) . . . . ? C18 N2 C19 C22 158.8(6) . . . . ? Zn1 N2 C19 C22 -24.2(6) . . . . ? C18 N2 C19 C21 -80.7(7) . . . . ? Zn1 N2 C19 C21 96.3(5) . . . . ? O4 C22 C19 N2 47.3(8) . . . . ? O4 C22 C19 C20 168.8(6) . . . . ? O4 C22 C19 C21 -70.0(8) . . . . ? C19 N2 C18 C17 -178.7(5) . . . . ? Zn1 N2 C18 C17 4.4(8) . . . . ? N2 C18 C17 C16 169.7(5) . . . . ? N2 C18 C17 C12 -7.5(9) . . . . ? Zn1 O3 C12 C13 -166.5(4) . . . . ? Zn1 O3 C12 C17 12.8(8) . . . . ? C16 C17 C12 O3 -178.9(5) . . . . ? C18 C17 C12 O3 -1.7(9) . . . . ? C16 C17 C12 C13 0.4(8) . . . . ? C18 C17 C12 C13 177.5(5) . . . . ? O3 C12 C13 C14 177.7(6) . . . . ? C17 C12 C13 C14 -1.6(9) . . . . ? C12 C13 C14 C15 1.0(10) . . . . ? C13 C14 C15 C16 0.8(10) . . . . ? C13 C14 C15 Br2 -178.0(5) . . . . ? C14 C15 C16 C17 -2.0(10) . . . . ? Br2 C15 C16 C17 176.7(4) . . . . ? C12 C17 C16 C15 1.4(9) . . . . ? C18 C17 C16 C15 -176.0(6) . . . . ? C3 C4 C5 C6 1.0(9) . . . . ? Br1 C4 C5 C6 -179.4(5) . . . . ? C1 C6 C5 C4 -0.3(9) . . . . ? C7 C6 C5 C4 -177.7(6) . . . . ? C19 C22 O4 Zn1 -46.1(8) . . . . ?