#------------------------------------------------------------------------------ #$Date: 2026-05-30 00:00:11 +0100 (Sat, 30 May 2026) $ #$Revision: 306135 $ #$URL: svn://www.crystallography.net/cod/cif/7/72/10/7721059.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_7721059 loop_ _publ_author_name 'Wan, Yong Qiang' 'Zhang, Yang Yang' 'Zhang, Shi Lin' 'Hao, Huai Xin' 'Bai, Ji Yao' 'Ma, Zhi Jun' 'Geng, Long' 'Wang, Zhipeng' 'Gallagher, John F.' 'Li, Jun' 'Mocilac, Pavle' _publ_section_title ; Development and Comparative Study of a Hydrophilic Bis-Triazolyl-Phenanthroline and Two Bis-Triazolyl-Pyridine Ligands ; _journal_name_full 'Dalton Transactions' _journal_paper_doi 10.1039/D6DT00312E _journal_year 2026 _chemical_formula_moiety 'C24 H26 N8 O4, H2 O' _chemical_formula_sum 'C24 H28 N8 O5' _chemical_formula_weight 508.54 _chemical_name_common DEG_BTrzPhen _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2019/3 _audit_update_record ; 2025-10-13 deposited with the CCDC. 2026-05-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 31.037(3) _cell_length_b 17.2042(16) _cell_length_c 4.3924(5) _cell_measurement_reflns_used 4026 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 72.538 _cell_measurement_theta_min 2.843 _cell_volume 2345.4(4) _computing_cell_refinement 'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.94a (Rigaku OD, 2023)' _computing_molecular_graphics 'Mercury program' _computing_publication_material 'Standard preparation' _computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.2(4) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_measured_fraction_theta_full 0.975 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Pro II AFC12 (RINC): Kappa dual' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_unetI/netI 0.0642 _diffrn_reflns_Laue_measured_fraction_full 0.975 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_number 11231 _diffrn_reflns_point_group_measured_fraction_full 0.677 _diffrn_reflns_point_group_measured_fraction_max 0.677 _diffrn_reflns_theta_full 73.605 _diffrn_reflns_theta_max 73.604 _diffrn_reflns_theta_min 2.847 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.866 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.72743 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.94a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.440 _exptl_crystal_description Plate _exptl_crystal_F_000 1072 _exptl_crystal_size_max 0.550 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.030 _refine_diff_density_max 0.286 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.073 _refine_ls_abs_structure_details ; Classical Flack method preferred over Parsons because s.u. lower. ; _refine_ls_abs_structure_Flack 0.1(6) _refine_ls_extinction_coef 0.0012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 347 _refine_ls_number_reflns 3209 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.102 _refine_ls_R_factor_all 0.0844 _refine_ls_R_factor_gt 0.0720 _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^)+(0.0143P)^2^+6.3495P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1399 _refine_ls_wR_factor_ref 0.1479 _reflns_Friedel_coverage 0.222 _reflns_Friedel_fraction_full 0.285 _reflns_Friedel_fraction_max 0.284 _reflns_number_gt 2804 _reflns_number_total 3209 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6dt00312e2.cif _cod_data_source_block 24-011-[DEG_BTrzPhen] _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_database_code 7721059 _shelx_shelxl_version_number 2019/3 _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_min 0.647 _shelx_estimated_absorpt_t_max 0.974 _shelx_res_file ; TITL 24-011 [WYQ_DEG-BTrzPhen-Tb] in Pna21 #33 at 100 K 24-011.res created by SHELXL-2019/3 at 11:19:40 on 06-Oct-2025 REM reset to Pna21 #33 CELL 1.54184 31.0374 17.2042 4.3924 90 90 90 ZERR 4 0.0029 0.0016 0.0005 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,0.5+Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SFAC C H N O UNIT 96 112 32 20 OMIT 20 1 3 OMIT 5 5 4 OMIT 13 3 5 OMIT 12 2 5 OMIT 13 2 5 MERG 2 FMAP 2 L.S. 8 3 LIST 4 ACTA 150 CONF BOND $H HTAB EQIV $1 X-1/2,-Y+1/2,Z EQIV $2 X,Y,Z-1 EQIV $3 -X+1,-Y+1,Z-1/2 EQIV $4 -X+1/2,Y+1/2,Z+1/2 HTAB O2 N45_$1 HTAB O4 O1W_$2 HTAB C5 N44_$3 HTAB C8 N34_$4 HTAB O1W O4 HTAB O1W N21 HTAB O1W N25 SIZE 0.03 0.07 0.55 TEMP -173 PLAN 10 MPLA 5 C41 C42 N43 N44 N45 O1W MPLA 5 C31 C32 N33 N34 N35 O1W MPLA 6 C11 C12 C13 C14 C15 C16 MPLA 14 C11 C12 C13 C14 C15 C16 N21 C22 C23 C24 N25 C26 C27 C28 MPLA 5 C31 C32 N33 N34 N35 O1W MPLA 14 C11 C12 C13 C14 C15 C16 N21 C22 C23 C24 N25 C26 C27 C28 MPLA 5 C41 C42 N43 N44 N45 O1W MPLA 6 N21 C22 C23 C24 C11 C12 MPLA 6 C11 C12 C13 C14 C15 C16 MPLA 6 N25 C26 C27 C28 C15 C16 WGHT 0.014300 6.349500 EXTI 0.001200 FVAR 1.35965 O1 4 0.181001 0.259026 0.093094 11.00000 0.01695 0.03506 = 0.02245 -0.00044 -0.00073 0.00135 O2 4 0.090110 0.248731 0.280508 11.00000 0.02240 0.05696 = 0.04212 -0.00907 0.00361 -0.00641 H2 2 0.070802 0.220800 0.349235 11.00000 -1.50000 O3 4 0.383179 0.483208 0.267789 11.00000 0.01928 0.02776 = 0.03276 0.00208 0.00197 0.00131 O4 4 0.319942 0.355422 0.222286 11.00000 0.03173 0.02356 = 0.04954 -0.00721 -0.00837 0.00330 H4 2 0.334145 0.343569 0.042486 11.00000 -1.50000 C1 1 0.239627 0.221854 -0.249612 11.00000 0.02095 0.02942 = 0.02631 0.00781 -0.00337 -0.00044 AFIX 23 H1A 2 0.219259 0.199031 -0.398258 11.00000 -1.20000 H1B 2 0.263940 0.244534 -0.365343 11.00000 -1.20000 AFIX 0 C2 1 0.216922 0.286247 -0.076382 11.00000 0.02137 0.02376 = 0.03139 0.00470 -0.00671 0.00032 AFIX 23 H2A 2 0.237682 0.311114 0.064319 11.00000 -1.20000 H2B 2 0.207048 0.326263 -0.222554 11.00000 -1.20000 AFIX 0 C3 1 0.144607 0.243895 -0.100208 11.00000 0.01929 0.04144 = 0.03419 -0.00362 -0.00335 0.00095 AFIX 23 H3A 2 0.153937 0.213757 -0.280537 11.00000 -1.20000 H3B 2 0.132170 0.293630 -0.171827 11.00000 -1.20000 AFIX 0 C4 1 0.111408 0.199162 0.072115 11.00000 0.02159 0.03251 = 0.04857 0.00070 -0.00668 -0.00113 AFIX 23 H4A 2 0.090210 0.176705 -0.071504 11.00000 -1.20000 H4B 2 0.125335 0.155918 0.183593 11.00000 -1.20000 AFIX 0 C5 1 0.442769 0.449394 -0.066482 11.00000 0.02101 0.02227 = 0.02863 0.00276 0.00063 -0.00220 AFIX 23 H5A 2 0.421787 0.425912 -0.209167 11.00000 -1.20000 H5B 2 0.466323 0.472715 -0.187963 11.00000 -1.20000 AFIX 0 C6 1 0.420645 0.512432 0.119047 11.00000 0.02282 0.01846 = 0.03508 -0.00246 -0.00104 0.00082 AFIX 23 H6A 2 0.440978 0.532862 0.273170 11.00000 -1.20000 H6B 2 0.412405 0.555864 -0.016863 11.00000 -1.20000 AFIX 0 C7 1 0.345999 0.485426 0.079147 11.00000 0.01868 0.03263 = 0.04115 0.00682 -0.00665 0.00517 AFIX 23 H7A 2 0.353461 0.465899 -0.126208 11.00000 -1.20000 H7B 2 0.336073 0.539852 0.058241 11.00000 -1.20000 AFIX 0 C8 1 0.310559 0.437205 0.208932 11.00000 0.02245 0.02466 = 0.03753 0.00285 -0.00495 0.00546 AFIX 23 H8A 2 0.304168 0.455889 0.417273 11.00000 -1.20000 H8B 2 0.284327 0.444936 0.084323 11.00000 -1.20000 AFIX 0 C11 1 0.387119 0.073443 0.718344 11.00000 0.01794 0.01619 = 0.01789 -0.00449 0.00332 0.00395 C12 1 0.384454 -0.000465 0.858813 11.00000 0.01809 0.02277 = 0.01993 -0.00457 0.00759 0.00580 C13 1 0.417578 -0.026932 1.057849 11.00000 0.02835 0.02029 = 0.03540 0.00188 0.00901 0.00611 AFIX 43 H13 2 0.415059 -0.076425 1.152091 11.00000 -1.20000 AFIX 0 C14 1 0.452667 0.017747 1.114266 11.00000 0.02001 0.02813 = 0.02139 0.00549 -0.00012 0.00933 AFIX 43 H14 2 0.473837 0.000532 1.255170 11.00000 -1.20000 AFIX 0 C15 1 0.457971 0.091044 0.961806 11.00000 0.01953 0.01939 = 0.02041 -0.00389 0.00432 0.00489 C16 1 0.425739 0.119374 0.774657 11.00000 0.01690 0.01712 = 0.02781 -0.00304 -0.00120 0.00402 N21 3 0.356711 0.101843 0.537752 11.00000 0.01644 0.01783 = 0.01652 -0.00079 -0.00069 0.00114 C22 1 0.322880 0.057636 0.470093 11.00000 0.01918 0.01938 = 0.02797 -0.00459 -0.00155 0.00122 C23 1 0.317470 -0.017634 0.593832 11.00000 0.02179 0.02257 = 0.03005 -0.00502 0.00081 -0.00272 AFIX 43 H23 2 0.292849 -0.047791 0.543233 11.00000 -1.20000 AFIX 0 C24 1 0.348228 -0.046654 0.788077 11.00000 0.02727 0.01889 = 0.02816 0.00215 0.00468 -0.00136 AFIX 43 H24 2 0.345153 -0.097078 0.873513 11.00000 -1.20000 AFIX 0 N25 3 0.429577 0.187375 0.618921 11.00000 0.01449 0.01551 = 0.02996 -0.00415 0.00190 0.00060 C26 1 0.466922 0.225981 0.638787 11.00000 0.01770 0.01831 = 0.02844 -0.00451 0.00027 0.00214 C27 1 0.501066 0.201087 0.823929 11.00000 0.01415 0.02246 = 0.02752 -0.00912 -0.00114 0.00290 AFIX 43 H27 2 0.527091 0.230073 0.832252 11.00000 -1.20000 AFIX 0 C28 1 0.496584 0.135069 0.991463 11.00000 0.01905 0.02355 = 0.03131 -0.00211 -0.00285 0.00629 AFIX 43 H28 2 0.518795 0.118660 1.125680 11.00000 -1.20000 AFIX 0 C31 1 0.290756 0.090142 0.269737 11.00000 0.01544 0.02182 = 0.01244 -0.00489 0.00121 -0.00086 C32 1 0.292676 0.158176 0.103607 11.00000 0.01278 0.02222 = 0.02593 -0.00345 0.00259 0.00070 AFIX 43 H32 2 0.315357 0.195253 0.102651 11.00000 -1.20000 AFIX 0 N33 3 0.255794 0.161084 -0.056551 11.00000 0.01703 0.02256 = 0.01724 -0.00138 0.00036 -0.00125 N34 3 0.231263 0.097445 0.004046 11.00000 0.02283 0.02410 = 0.02998 0.00255 -0.00695 -0.00387 N35 3 0.252416 0.054050 0.197658 11.00000 0.02022 0.02507 = 0.02356 0.00166 -0.00069 -0.00596 C41 1 0.470570 0.294948 0.448073 11.00000 0.01577 0.01846 = 0.03101 -0.00203 -0.00439 -0.00204 C42 1 0.439970 0.329762 0.262493 11.00000 0.01474 0.01576 = 0.03319 -0.00517 0.00363 -0.00121 AFIX 43 H42 2 0.410808 0.314551 0.234814 11.00000 -1.20000 AFIX 0 N43 3 0.460344 0.389117 0.131600 11.00000 0.01685 0.01934 = 0.02821 -0.00300 -0.00187 -0.00022 N44 3 0.502202 0.392271 0.216874 11.00000 0.01792 0.02115 = 0.03741 0.00155 0.00046 -0.00255 N45 3 0.508386 0.334990 0.410788 11.00000 0.01678 0.02415 = 0.03324 -0.00312 0.00115 -0.00347 O1W 4 0.355141 0.291861 0.722238 11.00000 0.04260 0.03381 = 0.04567 0.00109 0.00991 0.01475 H1W 2 0.339929 0.299042 0.554331 11.00000 -1.50000 H2W 2 0.369723 0.249544 0.675130 11.00000 -1.50000 DFIX 0.88 0.01 O1W H1W O1W H2W DANG 1.38 0.02 H1W H2W HKLF 4 REM 24-011 [WYQ_DEG-BTrzPhen-Tb] in Pna21 #33 at 100 K REM wR2 = 0.1479, GooF = S = 1.103, Restrained GooF = 1.102 for all data REM R1 = 0.0720 for 2804 Fo > 4sig(Fo) and 0.0844 for all 3209 data REM 347 parameters refined using 4 restraints END WGHT 0.0143 6.3496 REM Instructions for potential hydrogen bonds HTAB O2 N45_$1 HTAB O4 O1W_$2 HTAB C5 N44_$3 HTAB C8 N34_$4 HTAB O1W O4 HTAB O1W N21 HTAB O1W N25 REM Highest difference peak 0.286, deepest hole -0.404, 1-sigma level 0.073 Q1 1 0.4007 0.1093 0.8482 11.00000 0.05 0.29 Q2 1 0.2199 0.3443 -0.2550 11.00000 0.05 0.26 Q3 1 0.3080 0.1822 -0.3636 11.00000 0.05 0.26 Q4 1 0.3596 0.1313 0.3515 11.00000 0.05 0.26 Q5 1 0.3432 0.2683 0.5110 11.00000 0.05 0.25 Q6 1 0.3299 0.0861 -0.0167 11.00000 0.05 0.25 Q7 1 0.0876 0.3208 0.1977 11.00000 0.05 0.25 Q8 1 0.2901 -0.1000 0.8551 11.00000 0.05 0.25 Q9 1 0.2960 -0.0409 0.2542 11.00000 0.05 0.25 Q10 1 0.2962 0.1041 0.0802 11.00000 0.05 0.24 ; _shelx_res_checksum 72449 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, 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 O1 O 0.18100(11) 0.2590(2) 0.0931(11) 0.0248(10) Uani 1 1 d . . . . . O2 O 0.09011(13) 0.2487(3) 0.2805(14) 0.0405(13) Uani 1 1 d . . . . . H2 H 0.071(3) 0.221(5) 0.35(2) 0.061 Uiso 1 1 d . U . . . O3 O 0.38318(11) 0.4832(2) 0.2678(12) 0.0266(10) Uani 1 1 d . . . . . O4 O 0.31994(13) 0.3554(2) 0.2223(14) 0.0349(12) Uani 1 1 d . . . . . H4 H 0.334(2) 0.344(5) 0.04(2) 0.052 Uiso 1 1 d . U . . . C1 C 0.23963(17) 0.2219(3) -0.2496(17) 0.0256(14) Uani 1 1 d . . . . . H1A H 0.219259 0.199031 -0.398258 0.031 Uiso 1 1 calc R U . . . H1B H 0.263940 0.244534 -0.365343 0.031 Uiso 1 1 calc R U . . . C2 C 0.21692(17) 0.2862(3) -0.0764(17) 0.0255(14) Uani 1 1 d . . . . . H2A H 0.237682 0.311114 0.064319 0.031 Uiso 1 1 calc R U . . . H2B H 0.207048 0.326263 -0.222554 0.031 Uiso 1 1 calc R U . . . C3 C 0.14461(18) 0.2439(4) -0.1002(18) 0.0316(16) Uani 1 1 d . . . . . H3A H 0.153937 0.213757 -0.280537 0.038 Uiso 1 1 calc R U . . . H3B H 0.132170 0.293630 -0.171827 0.038 Uiso 1 1 calc R U . . . C4 C 0.11141(18) 0.1992(4) 0.072(2) 0.0342(17) Uani 1 1 d . . . . . H4A H 0.090210 0.176705 -0.071504 0.041 Uiso 1 1 calc R U . . . H4B H 0.125335 0.155918 0.183593 0.041 Uiso 1 1 calc R U . . . C5 C 0.44277(17) 0.4494(3) -0.0665(16) 0.0240(14) Uani 1 1 d . . . . . H5A H 0.421787 0.425912 -0.209167 0.029 Uiso 1 1 calc R U . . . H5B H 0.466323 0.472715 -0.187963 0.029 Uiso 1 1 calc R U . . . C6 C 0.42065(18) 0.5124(3) 0.1190(17) 0.0255(14) Uani 1 1 d . . . . . H6A H 0.440978 0.532862 0.273170 0.031 Uiso 1 1 calc R U . . . H6B H 0.412405 0.555864 -0.016863 0.031 Uiso 1 1 calc R U . . . C7 C 0.34600(17) 0.4854(3) 0.0791(19) 0.0308(16) Uani 1 1 d . . . . . H7A H 0.353461 0.465899 -0.126208 0.037 Uiso 1 1 calc R U . . . H7B H 0.336073 0.539852 0.058241 0.037 Uiso 1 1 calc R U . . . C8 C 0.31056(18) 0.4372(3) 0.2089(18) 0.0282(15) Uani 1 1 d . . . . . H8A H 0.304168 0.455889 0.417273 0.034 Uiso 1 1 calc R U . . . H8B H 0.284327 0.444936 0.084323 0.034 Uiso 1 1 calc R U . . . C11 C 0.38712(16) 0.0734(3) 0.7183(15) 0.0173(12) Uani 1 1 d . . . . . C12 C 0.38445(17) -0.0005(3) 0.8588(15) 0.0203(13) Uani 1 1 d . . . . . C13 C 0.41758(18) -0.0269(3) 1.0578(18) 0.0280(15) Uani 1 1 d . . . . . H13 H 0.415059 -0.076425 1.152091 0.034 Uiso 1 1 calc R U . . . C14 C 0.45267(17) 0.0177(3) 1.1143(16) 0.0232(13) Uani 1 1 d . . . . . H14 H 0.473837 0.000532 1.255170 0.028 Uiso 1 1 calc R U . . . C15 C 0.45797(17) 0.0910(3) 0.9618(15) 0.0198(12) Uani 1 1 d . . . . . C16 C 0.42574(16) 0.1194(3) 0.7747(16) 0.0206(13) Uani 1 1 d . . . . . N21 N 0.35671(13) 0.1018(2) 0.5378(12) 0.0169(10) Uani 1 1 d . . . . . C22 C 0.32288(17) 0.0576(3) 0.4701(16) 0.0222(14) Uani 1 1 d . . . . . C23 C 0.31747(17) -0.0176(3) 0.5938(16) 0.0248(14) Uani 1 1 d . . . . . H23 H 0.292849 -0.047791 0.543233 0.030 Uiso 1 1 calc R U . . . C24 C 0.34823(17) -0.0467(3) 0.7881(17) 0.0248(14) Uani 1 1 d . . . . . H24 H 0.345153 -0.097078 0.873513 0.030 Uiso 1 1 calc R U . . . N25 N 0.42958(13) 0.1874(2) 0.6189(14) 0.0200(11) Uani 1 1 d . . . . . C26 C 0.46692(16) 0.2260(3) 0.6388(16) 0.0215(13) Uani 1 1 d . . . . . C27 C 0.50107(16) 0.2011(3) 0.8239(16) 0.0214(14) Uani 1 1 d . . . . . H27 H 0.527091 0.230073 0.832252 0.026 Uiso 1 1 calc R U . . . C28 C 0.49658(18) 0.1351(3) 0.9915(17) 0.0246(14) Uani 1 1 d . . . . . H28 H 0.518795 0.118660 1.125680 0.030 Uiso 1 1 calc R U . . . C31 C 0.29076(16) 0.0901(3) 0.2697(14) 0.0166(11) Uani 1 1 d . . . . . C32 C 0.29268(16) 0.1582(3) 0.1036(15) 0.0203(13) Uani 1 1 d . . . . . H32 H 0.315357 0.195253 0.102651 0.024 Uiso 1 1 calc R U . . . N33 N 0.25579(13) 0.1611(3) -0.0566(12) 0.0189(10) Uani 1 1 d . . . . . N34 N 0.23126(15) 0.0974(3) 0.0040(14) 0.0256(12) Uani 1 1 d . . . . . N35 N 0.25242(14) 0.0540(3) 0.1977(13) 0.0230(11) Uani 1 1 d . . . . . C41 C 0.47057(16) 0.2949(3) 0.4481(16) 0.0217(13) Uani 1 1 d . . . . . C42 C 0.43997(16) 0.3298(3) 0.2625(16) 0.0212(13) Uani 1 1 d . . . . . H42 H 0.410808 0.314551 0.234814 0.025 Uiso 1 1 calc R U . . . N43 N 0.46034(13) 0.3891(2) 0.1316(13) 0.0215(11) Uani 1 1 d . . . . . N44 N 0.50220(14) 0.3923(2) 0.2169(15) 0.0255(12) Uani 1 1 d . . . . . N45 N 0.50839(14) 0.3350(3) 0.4108(14) 0.0247(12) Uani 1 1 d . . . . . O1W O 0.35514(15) 0.2919(3) 0.7222(14) 0.0407(13) Uani 1 1 d D . . . . H1W H 0.340(2) 0.299(4) 0.554(10) 0.061 Uiso 1 1 d D U . . . H2W H 0.370(2) 0.250(3) 0.675(17) 0.061 Uiso 1 1 d D 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 O1 0.0170(18) 0.035(2) 0.022(3) 0.000(2) -0.001(2) 0.0014(16) O2 0.022(2) 0.057(3) 0.042(3) -0.009(3) 0.004(2) -0.006(2) O3 0.0193(18) 0.0278(19) 0.033(3) 0.002(2) 0.002(2) 0.0013(15) O4 0.032(2) 0.0236(19) 0.050(3) -0.007(2) -0.008(3) 0.0033(17) C1 0.021(3) 0.029(3) 0.026(4) 0.008(3) -0.003(3) 0.000(2) C2 0.021(3) 0.024(3) 0.031(4) 0.005(3) -0.007(3) 0.000(2) C3 0.019(3) 0.041(3) 0.034(4) -0.004(3) -0.003(3) 0.001(3) C4 0.022(3) 0.033(3) 0.049(5) 0.001(3) -0.007(3) -0.001(2) C5 0.021(3) 0.022(3) 0.029(4) 0.003(3) 0.001(3) -0.002(2) C6 0.023(3) 0.018(2) 0.035(4) -0.002(3) -0.001(3) 0.001(2) C7 0.019(3) 0.033(3) 0.041(5) 0.007(3) -0.007(3) 0.005(2) C8 0.022(3) 0.025(3) 0.038(4) 0.003(3) -0.005(3) 0.005(2) C11 0.018(2) 0.016(2) 0.018(3) -0.004(2) 0.003(2) 0.0040(19) C12 0.018(3) 0.023(3) 0.020(3) -0.005(2) 0.008(2) 0.006(2) C13 0.028(3) 0.020(2) 0.035(4) 0.002(3) 0.009(3) 0.006(2) C14 0.020(3) 0.028(3) 0.021(4) 0.005(3) 0.000(3) 0.009(2) C15 0.020(2) 0.019(2) 0.020(3) -0.004(2) 0.004(3) 0.005(2) C16 0.017(2) 0.017(2) 0.028(4) -0.003(3) -0.001(3) 0.0040(19) N21 0.016(2) 0.018(2) 0.017(3) -0.0008(19) -0.001(2) 0.0011(17) C22 0.019(3) 0.019(2) 0.028(4) -0.005(3) -0.002(3) 0.001(2) C23 0.022(3) 0.023(3) 0.030(4) -0.005(3) 0.001(3) -0.003(2) C24 0.027(3) 0.019(2) 0.028(4) 0.002(3) 0.005(3) -0.001(2) N25 0.014(2) 0.0155(19) 0.030(3) -0.004(2) 0.002(2) 0.0006(16) C26 0.018(2) 0.018(2) 0.028(4) -0.005(3) 0.000(3) 0.002(2) C27 0.014(2) 0.022(3) 0.028(4) -0.009(3) -0.001(3) 0.003(2) C28 0.019(3) 0.024(3) 0.031(4) -0.002(3) -0.003(3) 0.006(2) C31 0.015(2) 0.022(2) 0.012(3) -0.005(2) 0.001(2) -0.0009(19) C32 0.013(2) 0.022(2) 0.026(4) -0.003(3) 0.003(3) 0.001(2) N33 0.017(2) 0.023(2) 0.017(3) -0.001(2) 0.000(2) -0.0013(18) N34 0.023(2) 0.024(2) 0.030(3) 0.003(2) -0.007(2) -0.0039(19) N35 0.020(2) 0.025(2) 0.024(3) 0.002(2) -0.001(2) -0.0060(18) C41 0.016(2) 0.018(2) 0.031(4) -0.002(3) -0.004(3) -0.002(2) C42 0.015(2) 0.016(2) 0.033(4) -0.005(3) 0.004(3) -0.0012(19) N43 0.017(2) 0.019(2) 0.028(3) -0.003(2) -0.002(2) -0.0002(17) N44 0.018(2) 0.021(2) 0.037(4) 0.002(3) 0.000(3) -0.0025(18) N45 0.017(2) 0.024(2) 0.033(3) -0.003(2) 0.001(2) -0.0035(19) O1W 0.043(3) 0.034(2) 0.046(4) 0.001(3) 0.010(3) 0.015(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C2 O1 C3 111.5(5) . . ? C4 O2 H2 103(6) . . ? C7 O3 C6 112.7(5) . . ? C8 O4 H4 106(5) . . ? N33 C1 C2 113.4(6) . . ? N33 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? N33 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? O1 C2 C1 112.7(4) . . ? O1 C2 H2A 109.0 . . ? C1 C2 H2A 109.0 . . ? O1 C2 H2B 109.0 . . ? C1 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? O1 C3 C4 109.7(6) . . ? O1 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? O1 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? O2 C4 C3 109.9(5) . . ? O2 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? O2 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? N43 C5 C6 110.9(6) . . ? N43 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? N43 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? O3 C6 C5 111.3(4) . . ? O3 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? O3 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? O3 C7 C8 111.2(6) . . ? O3 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? O3 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O4 C8 C7 114.2(5) . . ? O4 C8 H8A 108.7 . . ? C7 C8 H8A 108.7 . . ? O4 C8 H8B 108.7 . . ? C7 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? N21 C11 C12 123.4(5) . . ? N21 C11 C16 119.2(5) . . ? C12 C11 C16 117.5(5) . . ? C24 C12 C11 117.1(5) . . ? C24 C12 C13 122.0(5) . . ? C11 C12 C13 120.8(5) . . ? C14 C13 C12 120.7(5) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 120.3(6) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C28 118.4(5) . . ? C16 C15 C14 120.2(5) . . ? C28 C15 C14 121.4(5) . . ? N25 C16 C15 122.6(5) . . ? N25 C16 C11 116.9(5) . . ? C15 C16 C11 120.3(5) . . ? C11 N21 C22 119.0(5) . . ? N21 C22 C23 122.1(5) . . ? N21 C22 C31 117.4(5) . . ? C23 C22 C31 120.5(5) . . ? C24 C23 C22 119.3(5) . . ? C24 C23 H23 120.4 . . ? C22 C23 H23 120.4 . . ? C23 C24 C12 119.0(5) . . ? C23 C24 H24 120.5 . . ? C12 C24 H24 120.5 . . ? C26 N25 C16 118.0(5) . . ? N25 C26 C27 122.7(5) . . ? N25 C26 C41 115.7(5) . . ? C27 C26 C41 121.6(5) . . ? C28 C27 C26 119.4(5) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? C27 C28 C15 118.7(6) . . ? C27 C28 H28 120.6 . . ? C15 C28 H28 120.6 . . ? N35 C31 C32 107.3(5) . . ? N35 C31 C22 124.2(5) . . ? C32 C31 C22 128.4(5) . . ? N33 C32 C31 105.7(5) . . ? N33 C32 H32 127.1 . . ? C31 C32 H32 127.1 . . ? C32 N33 N34 110.1(5) . . ? C32 N33 C1 129.3(5) . . ? N34 N33 C1 120.4(4) . . ? N35 N34 N33 107.8(4) . . ? N34 N35 C31 109.0(4) . . ? N45 C41 C42 107.4(5) . . ? N45 C41 C26 123.0(5) . . ? C42 C41 C26 129.5(5) . . ? N43 C42 C41 105.0(5) . . ? N43 C42 H42 127.5 . . ? C41 C42 H42 127.5 . . ? C42 N43 N44 111.5(5) . . ? C42 N43 C5 128.7(5) . . ? N44 N43 C5 119.7(4) . . ? N45 N44 N43 106.8(4) . . ? N44 N45 C41 109.2(5) . . ? H1W O1W H2W 101(3) . . ? 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 O1 C2 1.420(7) . ? O1 C3 1.437(7) . ? O2 C4 1.415(9) . ? O2 H2 0.83(8) . ? O3 C7 1.421(7) . ? O3 C6 1.425(7) . ? O4 C8 1.438(6) . ? O4 H4 0.93(9) . ? C1 N33 1.437(7) . ? C1 C2 1.518(8) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.492(9) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N43 1.459(7) . ? C5 C6 1.520(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.491(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C11 N21 1.326(7) . ? C11 C12 1.416(8) . ? C11 C16 1.457(7) . ? C12 C24 1.411(8) . ? C12 C13 1.424(9) . ? C13 C14 1.356(8) . ? C13 H13 0.9500 . ? C14 C15 1.437(8) . ? C14 H14 0.9500 . ? C15 C16 1.384(8) . ? C15 C28 1.424(8) . ? C16 N25 1.360(7) . ? N21 C22 1.330(7) . ? C22 C23 1.414(8) . ? C22 C31 1.443(8) . ? C23 C24 1.374(9) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? N25 C26 1.339(6) . ? C26 C27 1.403(8) . ? C26 C41 1.457(8) . ? C27 C28 1.360(8) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C31 N35 1.379(6) . ? C31 C32 1.381(8) . ? C32 N33 1.345(7) . ? C32 H32 0.9500 . ? N33 N34 1.360(6) . ? N34 N35 1.308(7) . ? C41 N45 1.371(7) . ? C41 C42 1.388(8) . ? C42 N43 1.332(7) . ? C42 H42 0.9500 . ? N43 N44 1.353(6) . ? N44 N45 1.317(7) . ? O1W H1W 0.884(12) . ? O1W H2W 0.882(12) . ? 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 O2 H2 N45 0.83(8) 2.18(8) 2.973(6) 161(9) 4_455 yes O4 H4 O1W 0.93(9) 1.79(9) 2.686(8) 162(7) 1_554 yes C5 H5B N44 0.99 2.55 3.353(7) 137.7 2_664 yes O1W H1W O4 0.884(12) 1.86(4) 2.685(8) 155(7) . yes O1W H2W N25 0.882(12) 2.16(3) 2.962(6) 151(6) . 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 C3 O1 C2 C1 -76.1(6) . . . . ? N33 C1 C2 O1 -59.5(7) . . . . ? C2 O1 C3 C4 167.3(5) . . . . ? O1 C3 C4 O2 74.4(7) . . . . ? C7 O3 C6 C5 -85.6(6) . . . . ? N43 C5 C6 O3 -66.4(6) . . . . ? C6 O3 C7 C8 165.8(5) . . . . ? O3 C7 C8 O4 -64.7(8) . . . . ? N21 C11 C12 C24 3.1(9) . . . . ? C16 C11 C12 C24 -176.1(6) . . . . ? N21 C11 C12 C13 -178.1(6) . . . . ? C16 C11 C12 C13 2.7(8) . . . . ? C24 C12 C13 C14 177.9(6) . . . . ? C11 C12 C13 C14 -0.8(9) . . . . ? C12 C13 C14 C15 -3.1(9) . . . . ? C13 C14 C15 C16 5.1(9) . . . . ? C13 C14 C15 C28 -173.1(6) . . . . ? C28 C15 C16 N25 0.0(9) . . . . ? C14 C15 C16 N25 -178.2(6) . . . . ? C28 C15 C16 C11 175.1(6) . . . . ? C14 C15 C16 C11 -3.1(9) . . . . ? N21 C11 C16 N25 -4.5(9) . . . . ? C12 C11 C16 N25 174.7(5) . . . . ? N21 C11 C16 C15 -179.9(6) . . . . ? C12 C11 C16 C15 -0.7(9) . . . . ? C12 C11 N21 C22 -3.7(9) . . . . ? C16 C11 N21 C22 175.4(5) . . . . ? C11 N21 C22 C23 2.5(9) . . . . ? C11 N21 C22 C31 -179.2(5) . . . . ? N21 C22 C23 C24 -0.6(9) . . . . ? C31 C22 C23 C24 -178.9(6) . . . . ? C22 C23 C24 C12 0.0(9) . . . . ? C11 C12 C24 C23 -1.1(9) . . . . ? C13 C12 C24 C23 -179.9(6) . . . . ? C15 C16 N25 C26 3.1(9) . . . . ? C11 C16 N25 C26 -172.2(5) . . . . ? C16 N25 C26 C27 -3.2(9) . . . . ? C16 N25 C26 C41 175.1(5) . . . . ? N25 C26 C27 C28 0.1(9) . . . . ? C41 C26 C27 C28 -178.1(6) . . . . ? C26 C27 C28 C15 3.1(9) . . . . ? C16 C15 C28 C27 -3.1(9) . . . . ? C14 C15 C28 C27 175.1(6) . . . . ? N21 C22 C31 N35 -174.7(5) . . . . ? C23 C22 C31 N35 3.6(9) . . . . ? N21 C22 C31 C32 9.3(9) . . . . ? C23 C22 C31 C32 -172.4(6) . . . . ? N35 C31 C32 N33 0.8(6) . . . . ? C22 C31 C32 N33 177.3(6) . . . . ? C31 C32 N33 N34 -0.1(6) . . . . ? C31 C32 N33 C1 175.0(6) . . . . ? C2 C1 N33 C32 -82.6(7) . . . . ? C2 C1 N33 N34 92.1(6) . . . . ? C32 N33 N34 N35 -0.7(7) . . . . ? C1 N33 N34 N35 -176.3(5) . . . . ? N33 N34 N35 C31 1.2(7) . . . . ? C32 C31 N35 N34 -1.3(7) . . . . ? C22 C31 N35 N34 -178.0(5) . . . . ? N25 C26 C41 N45 -171.1(6) . . . . ? C27 C26 C41 N45 7.2(9) . . . . ? N25 C26 C41 C42 4.7(10) . . . . ? C27 C26 C41 C42 -177.0(6) . . . . ? N45 C41 C42 N43 -1.5(7) . . . . ? C26 C41 C42 N43 -177.9(6) . . . . ? C41 C42 N43 N44 1.8(7) . . . . ? C41 C42 N43 C5 -174.5(6) . . . . ? C6 C5 N43 C42 80.4(7) . . . . ? C6 C5 N43 N44 -95.7(6) . . . . ? C42 N43 N44 N45 -1.4(7) . . . . ? C5 N43 N44 N45 175.3(5) . . . . ? N43 N44 N45 C41 0.4(7) . . . . ? C42 C41 N45 N44 0.7(7) . . . . ? C26 C41 N45 N44 177.4(6) . . . . ?