#------------------------------------------------------------------------------ #$Date: 2021-09-25 03:36:07 +0300 (Sat, 25 Sep 2021) $ #$Revision: 269305 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060969.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_7060969 loop_ _publ_author_name 'Zhang, Yunan' 'Duan, Yu' 'Su, Jin' 'Liu, Lixin' 'Feng, Yanru' 'Zhang, Lei' 'Zhang, Yunjie' 'Wu, Lili' 'Zou, Dongyu' 'Liu, Yingli' _publ_section_title ; Inspiration for revival of old drug: Improving solubility and avoiding hygroscopicity of pipemidic acid by forming two pharmaceutical salts based on charge-assisted hydrogen bond recognitions ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ03314J _journal_year 2021 _chemical_formula_moiety 'C14 H18 N5 O3, C7 H5 O3, C7 H6 O3, 2(H2 O)' _chemical_formula_sum 'C28 H33 N5 O11' _chemical_formula_weight 615.59 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2021-06-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-09-20 deposited with the CCDC. 2021-09-21 downloaded from the CCDC. ; _cell_angle_alpha 106.133(8) _cell_angle_beta 103.719(7) _cell_angle_gamma 96.363(7) _cell_formula_units_Z 2 _cell_length_a 8.0857(7) _cell_length_b 12.8969(12) _cell_length_c 15.2536(13) _cell_measurement_reflns_used 2789 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.1420 _cell_measurement_theta_min 4.1350 _cell_volume 1457.6(2) _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _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 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 298.15 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.819 _diffrn_measurement_device_type 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0254 _diffrn_reflns_av_unetI/netI 0.0608 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.819 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 11385 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.819 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.533 _diffrn_reflns_theta_min 3.535 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.70914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.403 _exptl_crystal_description block _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.239 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 418 _refine_ls_number_reflns 6655 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0610 _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^)+(0.0456P)^2^+0.2682P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1135 _refine_ls_wR_factor_ref 0.1351 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4165 _reflns_number_total 6655 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj03314j2.cif _cod_data_source_block 1 _cod_database_code 7060969 _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 0.988 _shelx_estimated_absorpt_t_min 0.985 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups, All O(H,H) groups 2.a Free rotating group: O10(H10A,H10B), O11(H11A,H11B) 2.b Secondary CH2 refined with riding coordinates: N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C13(H13A,H13B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6), C9(H9), C17(H17), C18(H18), C19(H19), C24(H24), C26(H26), C27(H27), C28(H28) 2.d Idealised Me refined as rotating group: C14(H14A,H14B,H14C) 2.e Idealised tetrahedral OH refined as rotating group: O2(H2), O4(H4) ; _shelx_res_file ; TITL SIR97 run in space group P -1 1.res created by SHELXL-2018/3 at 16:23:07 on 16-Jun-2021 CELL 0.71073 8.0857 12.8969 15.2536 106.133 103.719 96.363 ZERR 2 0.0007 0.0012 0.0013 0.008 0.007 0.007 LATT 1 SFAC C H N O UNIT 56 66 10 22 L.S. 10 PLAN 50 SIZE 0.11 0.13 0.14 TEMP 25 BOND $H CONF fmap 2 acta MERG 2 REM REM REM WGHT 0.045600 0.268200 FVAR 0.14105 O1 4 0.094634 0.773901 0.208939 11.00000 0.05362 0.02914 = 0.06559 0.00975 0.00729 0.00601 O2 4 -0.123390 0.687957 0.081607 11.00000 0.06741 0.03949 = 0.06043 0.02258 -0.00176 0.01258 AFIX 147 H2 2 -0.172668 0.624576 0.050998 11.00000 -1.50000 AFIX 0 O3 4 -0.194865 0.483331 0.020800 11.00000 0.05769 0.04179 = 0.03857 0.01776 -0.00375 0.00868 N1 3 -0.062004 -0.037954 0.261564 11.00000 0.03522 0.03555 = 0.04266 0.01891 0.01538 0.01023 AFIX 23 H1A 2 0.004737 -0.088257 0.253436 11.00000 -1.20000 H1B 2 -0.128820 -0.054181 0.296453 11.00000 -1.20000 AFIX 0 N2 3 0.045562 0.099912 0.162998 11.00000 0.04756 0.02735 = 0.03644 0.01252 0.00481 -0.00114 N3 3 -0.115452 0.184286 0.066277 11.00000 0.05315 0.02812 = 0.02882 0.00959 0.00324 0.00067 N4 3 0.105026 0.288272 0.210850 11.00000 0.03671 0.02706 = 0.03223 0.01137 0.00610 0.00354 N5 3 0.166593 0.478534 0.258244 11.00000 0.03347 0.02801 = 0.02986 0.00719 0.00334 0.00248 C1 1 -0.173573 -0.042588 0.167312 11.00000 0.03871 0.02826 = 0.04533 0.01064 0.00194 0.00437 AFIX 23 H1C 2 -0.255884 0.005991 0.175928 11.00000 -1.20000 H1D 2 -0.238216 -0.116795 0.133811 11.00000 -1.20000 AFIX 0 C2 1 -0.062725 -0.008192 0.109498 11.00000 0.05874 0.02531 = 0.03548 0.01042 0.00871 0.00622 AFIX 23 H2A 2 0.010180 -0.061640 0.094591 11.00000 -1.20000 H2B 2 -0.136361 -0.005518 0.050174 11.00000 -1.20000 AFIX 0 C3 1 0.049908 0.072340 0.313507 11.00000 0.05314 0.03201 = 0.03389 0.01070 0.00265 0.00710 AFIX 23 H3A 2 0.124310 0.071466 0.373302 11.00000 -1.20000 H3B 2 -0.021690 0.126941 0.327260 11.00000 -1.20000 AFIX 0 C4 1 0.158749 0.101346 0.253080 11.00000 0.03956 0.03324 = 0.05115 0.02005 0.00003 0.00341 AFIX 23 H4A 2 0.230339 0.173802 0.285683 11.00000 -1.20000 H4B 2 0.234434 0.048748 0.241916 11.00000 -1.20000 AFIX 0 C5 1 0.011908 0.193903 0.146985 11.00000 0.04010 0.02908 = 0.03062 0.01185 0.01183 0.00158 C6 1 -0.141360 0.277088 0.050860 11.00000 0.04699 0.03557 = 0.02700 0.01111 0.00272 0.00176 AFIX 43 H6 2 -0.225794 0.273648 -0.003747 11.00000 -1.20000 AFIX 0 C7 1 -0.050586 0.380577 0.110993 11.00000 0.03603 0.02912 = 0.02588 0.00865 0.00777 0.00170 C8 1 0.072619 0.379925 0.192216 11.00000 0.03109 0.02742 = 0.02743 0.00784 0.00931 0.00281 C9 1 0.139008 0.573412 0.242117 11.00000 0.03623 0.02602 = 0.03465 0.00528 0.01156 0.00304 AFIX 43 H9 2 0.204335 0.638725 0.286826 11.00000 -1.20000 AFIX 0 C10 1 0.021613 0.579707 0.164553 11.00000 0.03554 0.02828 = 0.03212 0.00977 0.01076 0.00650 C11 1 -0.082616 0.481085 0.093361 11.00000 0.03883 0.03280 = 0.02829 0.01007 0.00902 0.00563 C12 1 0.001995 0.687724 0.153967 11.00000 0.04329 0.03304 = 0.04538 0.01298 0.01611 0.00999 C13 1 0.295796 0.479283 0.345712 11.00000 0.03553 0.03546 = 0.04012 0.00996 -0.00320 0.00562 AFIX 23 H13A 2 0.377558 0.548569 0.370955 11.00000 -1.20000 H13B 2 0.359918 0.420841 0.329711 11.00000 -1.20000 AFIX 0 C14 1 0.212846 0.464152 0.420734 11.00000 0.06134 0.05473 = 0.03762 0.01727 0.00468 0.01450 AFIX 137 H14A 2 0.135915 0.394082 0.397150 11.00000 -1.50000 H14B 2 0.148513 0.521520 0.436503 11.00000 -1.50000 H14C 2 0.301101 0.467184 0.476493 11.00000 -1.50000 AFIX 0 O4 4 0.855186 0.089650 0.573041 11.00000 0.02866 0.06429 = 0.07042 0.03871 0.01937 0.01925 AFIX 147 H4 2 0.942144 0.118675 0.563796 11.00000 -1.50000 AFIX 0 O5 4 0.292962 0.099974 0.651070 11.00000 0.03471 0.08106 = 0.05010 0.03651 0.01616 0.01020 O6 4 0.145634 0.181227 0.555795 11.00000 0.02406 0.04593 = 0.06009 0.01504 0.01063 0.00870 C15 1 0.280461 0.147928 0.589508 11.00000 0.02815 0.03491 = 0.03432 0.00557 0.00790 0.00454 C16 1 0.434636 0.167796 0.553680 11.00000 0.02456 0.03108 = 0.02734 0.00740 0.00340 0.00205 C17 1 0.435658 0.233116 0.494924 11.00000 0.02894 0.03774 = 0.04246 0.01781 0.00486 0.01024 AFIX 43 H17 2 0.340850 0.265425 0.477958 11.00000 -1.20000 AFIX 0 C18 1 0.577845 0.249742 0.461956 11.00000 0.04137 0.04672 = 0.04762 0.02872 0.01102 0.00652 AFIX 43 H18 2 0.577691 0.292843 0.422155 11.00000 -1.20000 AFIX 0 C19 1 0.720049 0.203498 0.487070 11.00000 0.02874 0.04862 = 0.04196 0.01858 0.01359 0.00392 AFIX 43 H19 2 0.815197 0.215407 0.464380 11.00000 -1.20000 AFIX 0 C20 1 0.720900 0.139258 0.546175 11.00000 0.02353 0.03518 = 0.03416 0.01022 0.00486 0.00557 C21 1 0.577645 0.121428 0.578871 11.00000 0.02961 0.03410 = 0.03660 0.01766 0.00792 0.00673 H21 2 0.577135 0.071644 0.615494 11.00000 0.03326 O7 4 -0.552503 0.181123 0.115066 11.00000 0.07221 0.04362 = 0.08847 0.00758 -0.00699 -0.00038 H7 2 -0.554545 0.100503 0.108564 11.00000 0.13115 O8 4 -0.329506 0.197272 0.238183 11.00000 0.08817 0.04422 = 0.07141 0.01482 0.00704 0.01774 O9 4 -0.130889 0.603530 0.388138 11.00000 0.05937 0.04192 = 0.05759 0.00999 -0.00521 0.00993 H9A 2 -0.136903 0.675167 0.399763 11.00000 0.10597 C22 1 -0.423133 0.238605 0.189842 11.00000 0.04804 0.04445 = 0.05092 0.00948 0.01799 0.00980 C23 1 -0.403469 0.359428 0.207342 11.00000 0.03963 0.04065 = 0.04684 0.01109 0.01870 0.00667 C24 1 -0.280057 0.427713 0.288441 11.00000 0.03890 0.04164 = 0.04542 0.01704 0.01429 0.01315 AFIX 43 H24 2 -0.213411 0.397654 0.330081 11.00000 -1.20000 AFIX 0 C25 1 -0.255569 0.540510 0.307730 11.00000 0.03694 0.04078 = 0.04237 0.01091 0.01147 0.00710 C26 1 -0.354278 0.584622 0.245051 11.00000 0.04992 0.03567 = 0.05351 0.01539 0.01342 0.01014 AFIX 43 H26 2 -0.337654 0.660361 0.257236 11.00000 -1.20000 AFIX 0 C27 1 -0.477462 0.516034 0.164408 11.00000 0.05176 0.05483 = 0.05122 0.02136 0.00370 0.01339 AFIX 43 H27 2 -0.544002 0.545956 0.122612 11.00000 -1.20000 AFIX 0 C28 1 -0.502686 0.403710 0.145307 11.00000 0.04650 0.04985 = 0.04688 0.00694 0.00582 0.00487 AFIX 43 H28 2 -0.586050 0.357952 0.090950 11.00000 -1.20000 AFIX 6 O10 4 -0.402017 0.030068 -0.080805 11.00000 0.09337 0.04419 = 0.07538 0.01109 -0.02504 -0.00637 H10A 2 -0.320529 0.068852 -0.032196 11.00000 -1.50000 H10B 2 -0.410892 0.067875 -0.118717 11.00000 -1.50000 AFIX 6 O11 4 -0.428808 0.163878 -0.189276 11.00000 0.06397 0.15832 = 0.06774 0.05790 0.00158 -0.01444 H11A 2 -0.339450 0.184507 -0.204798 11.00000 -1.50000 H11B 2 -0.511141 0.146348 -0.240254 11.00000 -1.50000 AFIX 0 HKLF 4 REM SIR97 run in space group P -1 REM wR2 = 0.1351, GooF = S = 1.028, Restrained GooF = 1.028 for all data REM R1 = 0.0610 for 4165 Fo > 4sig(Fo) and 0.1090 for all 6655 data REM 418 parameters refined using 0 restraints END WGHT 0.0456 0.2682 REM Highest difference peak 0.239, deepest hole -0.227, 1-sigma level 0.044 Q1 1 -0.4193 0.0826 -0.2335 11.00000 0.05 0.24 Q2 1 -0.0739 0.5379 0.1551 11.00000 0.05 0.21 Q3 1 0.6769 0.1653 0.5905 11.00000 0.05 0.17 Q4 1 0.1524 0.8392 0.1504 11.00000 0.05 0.17 Q5 1 -0.0362 0.3872 0.1612 11.00000 0.05 0.17 Q6 1 -0.5279 -0.0133 -0.2656 11.00000 0.05 0.17 Q7 1 0.1907 0.0396 0.6348 11.00000 0.05 0.16 Q8 1 -0.0433 0.3428 0.0578 11.00000 0.05 0.16 Q9 1 -0.2132 0.1237 0.0715 11.00000 0.05 0.15 Q10 1 0.4007 0.5432 0.3532 11.00000 0.05 0.15 Q11 1 -0.0579 0.4227 0.0984 11.00000 0.05 0.15 Q12 1 0.0325 0.3840 0.1356 11.00000 0.05 0.15 Q13 1 -0.1040 0.1832 0.1228 11.00000 0.05 0.15 Q14 1 0.0181 0.5368 0.1286 11.00000 0.05 0.15 Q15 1 -0.1844 0.0470 0.1974 11.00000 0.05 0.15 Q16 1 0.0228 0.0858 0.3804 11.00000 0.05 0.15 Q17 1 0.6768 0.1388 0.4909 11.00000 0.05 0.15 Q18 1 -0.1417 0.1265 0.0057 11.00000 0.05 0.14 Q19 1 -0.0716 -0.0191 0.0367 11.00000 0.05 0.14 Q20 1 0.5262 0.1756 0.5874 11.00000 0.05 0.14 Q21 1 0.3649 0.1352 0.5581 11.00000 0.05 0.14 Q22 1 -0.2039 0.2412 0.2866 11.00000 0.05 0.14 Q23 1 -0.0943 0.5934 -0.0395 11.00000 0.05 0.14 Q24 1 0.4062 0.1647 0.4955 11.00000 0.05 0.14 Q25 1 -0.5462 0.1859 0.0039 11.00000 0.05 0.14 Q26 1 -0.2182 0.6820 0.1747 11.00000 0.05 0.14 Q27 1 -0.1593 0.7423 0.1584 11.00000 0.05 0.14 Q28 1 0.3601 0.4788 0.2421 11.00000 0.05 0.14 Q29 1 0.1485 0.7434 0.1478 11.00000 0.05 0.14 Q30 1 0.9119 0.1560 0.6461 11.00000 0.05 0.13 Q31 1 0.6923 0.1158 0.7085 11.00000 0.05 0.13 Q32 1 -0.0744 0.3030 0.3084 11.00000 0.05 0.13 Q33 1 -0.0613 0.1449 0.3754 11.00000 0.05 0.13 Q34 1 -0.2778 0.0076 0.2106 11.00000 0.05 0.13 Q35 1 -0.1435 0.3210 0.2471 11.00000 0.05 0.13 Q36 1 0.0851 0.6826 0.4157 11.00000 0.05 0.13 Q37 1 0.0005 0.7621 0.2237 11.00000 0.05 0.13 Q38 1 -0.0239 0.6425 0.3385 11.00000 0.05 0.13 Q39 1 -0.5091 0.0318 0.0165 11.00000 0.05 0.13 Q40 1 1.0366 0.1221 0.5435 11.00000 0.05 0.13 Q41 1 -0.3567 0.1414 0.0512 11.00000 0.05 0.13 Q42 1 -0.1362 0.1001 0.3318 11.00000 0.05 0.13 Q43 1 0.4971 0.4651 0.3492 11.00000 0.05 0.13 Q44 1 -0.2277 0.4848 0.2738 11.00000 0.05 0.13 Q45 1 1.0225 0.1757 0.5831 11.00000 0.05 0.13 Q46 1 -0.4223 0.2454 0.2576 11.00000 0.05 0.13 Q47 1 0.5461 0.5683 0.3501 11.00000 0.05 0.13 Q48 1 0.1916 0.2227 0.4888 11.00000 0.05 0.13 Q49 1 -0.2345 0.5626 0.4163 11.00000 0.05 0.13 Q50 1 -0.4250 0.3649 0.2797 11.00000 0.05 0.12 ; _shelx_res_checksum 13904 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 0.0946(2) 0.77390(13) 0.20894(12) 0.0524(5) Uani 1 1 d . . . . . O2 O -0.1234(2) 0.68796(14) 0.08161(13) 0.0577(5) Uani 1 1 d . . . . . H2 H -0.172668 0.624576 0.050998 0.086 Uiso 1 1 calc GR . . . . O3 O -0.1949(2) 0.48333(13) 0.02080(11) 0.0481(4) Uani 1 1 d . . . . . N1 N -0.0620(2) -0.03795(14) 0.26156(12) 0.0353(4) Uani 1 1 d . . . . . H1A H 0.004737 -0.088257 0.253436 0.042 Uiso 1 1 calc R . . . . H1B H -0.128820 -0.054181 0.296453 0.042 Uiso 1 1 calc R . . . . N2 N 0.0456(2) 0.09991(14) 0.16300(13) 0.0385(5) Uani 1 1 d . . . . . N3 N -0.1155(2) 0.18429(14) 0.06628(12) 0.0386(5) Uani 1 1 d . . . . . N4 N 0.1050(2) 0.28827(14) 0.21085(12) 0.0324(4) Uani 1 1 d . . . . . N5 N 0.1666(2) 0.47853(14) 0.25824(12) 0.0321(4) Uani 1 1 d . . . . . C1 C -0.1736(3) -0.04259(18) 0.16731(16) 0.0396(6) Uani 1 1 d . . . . . H1C H -0.255884 0.005991 0.175928 0.047 Uiso 1 1 calc R . . . . H1D H -0.238216 -0.116795 0.133811 0.047 Uiso 1 1 calc R . . . . C2 C -0.0627(3) -0.00819(17) 0.10950(16) 0.0406(6) Uani 1 1 d . . . . . H2A H 0.010180 -0.061640 0.094591 0.049 Uiso 1 1 calc R . . . . H2B H -0.136361 -0.005518 0.050174 0.049 Uiso 1 1 calc R . . . . C3 C 0.0499(3) 0.07234(18) 0.31351(16) 0.0414(6) Uani 1 1 d . . . . . H3A H 0.124310 0.071466 0.373302 0.050 Uiso 1 1 calc R . . . . H3B H -0.021690 0.126941 0.327260 0.050 Uiso 1 1 calc R . . . . C4 C 0.1587(3) 0.10135(19) 0.25308(17) 0.0424(6) Uani 1 1 d . . . . . H4A H 0.230339 0.173802 0.285683 0.051 Uiso 1 1 calc R . . . . H4B H 0.234434 0.048748 0.241916 0.051 Uiso 1 1 calc R . . . . C5 C 0.0119(3) 0.19390(17) 0.14698(15) 0.0328(5) Uani 1 1 d . . . . . C6 C -0.1414(3) 0.27709(18) 0.05086(15) 0.0381(5) Uani 1 1 d . . . . . H6 H -0.225794 0.273648 -0.003747 0.046 Uiso 1 1 calc R . . . . C7 C -0.0506(3) 0.38058(17) 0.11099(14) 0.0309(5) Uani 1 1 d . . . . . C8 C 0.0726(3) 0.37993(16) 0.19222(14) 0.0288(5) Uani 1 1 d . . . . . C9 C 0.1390(3) 0.57341(17) 0.24212(15) 0.0332(5) Uani 1 1 d . . . . . H9 H 0.204335 0.638725 0.286826 0.040 Uiso 1 1 calc R . . . . C10 C 0.0216(3) 0.57971(17) 0.16455(14) 0.0317(5) Uani 1 1 d . . . . . C11 C -0.0826(3) 0.48109(17) 0.09336(15) 0.0334(5) Uani 1 1 d . . . . . C12 C 0.0020(3) 0.68772(18) 0.15397(17) 0.0395(5) Uani 1 1 d . . . . . C13 C 0.2958(3) 0.47928(19) 0.34571(16) 0.0400(6) Uani 1 1 d . . . . . H13A H 0.377558 0.548569 0.370955 0.048 Uiso 1 1 calc R . . . . H13B H 0.359918 0.420841 0.329711 0.048 Uiso 1 1 calc R . . . . C14 C 0.2128(3) 0.4642(2) 0.42073(17) 0.0520(7) Uani 1 1 d . . . . . H14A H 0.135915 0.394082 0.397150 0.078 Uiso 1 1 calc GR . . . . H14B H 0.148513 0.521520 0.436503 0.078 Uiso 1 1 calc GR . . . . H14C H 0.301101 0.467184 0.476493 0.078 Uiso 1 1 calc GR . . . . O4 O 0.85519(18) 0.08965(14) 0.57304(13) 0.0489(4) Uani 1 1 d . . . . . H4 H 0.942144 0.118675 0.563796 0.073 Uiso 1 1 calc GR . . . . O5 O 0.29296(19) 0.09997(15) 0.65107(12) 0.0512(5) Uani 1 1 d . . . . . O6 O 0.14563(17) 0.18123(13) 0.55580(12) 0.0438(4) Uani 1 1 d . . . . . C15 C 0.2805(3) 0.14793(18) 0.58951(15) 0.0339(5) Uani 1 1 d . . . . . C16 C 0.4346(2) 0.16780(16) 0.55368(14) 0.0290(5) Uani 1 1 d . . . . . C17 C 0.4357(3) 0.23312(18) 0.49492(15) 0.0359(5) Uani 1 1 d . . . . . H17 H 0.340850 0.265425 0.477958 0.043 Uiso 1 1 calc R . . . . C18 C 0.5778(3) 0.24974(19) 0.46196(16) 0.0427(6) Uani 1 1 d . . . . . H18 H 0.577691 0.292843 0.422155 0.051 Uiso 1 1 calc R . . . . C19 C 0.7200(3) 0.20350(19) 0.48707(16) 0.0385(5) Uani 1 1 d . . . . . H19 H 0.815197 0.215407 0.464380 0.046 Uiso 1 1 calc R . . . . C20 C 0.7209(2) 0.13926(17) 0.54617(15) 0.0317(5) Uani 1 1 d . . . . . C21 C 0.5776(3) 0.12143(18) 0.57887(15) 0.0322(5) Uani 1 1 d . . . . . H21 H 0.577(2) 0.0716(17) 0.6155(14) 0.033(6) Uiso 1 1 d . . . . . O7 O -0.5525(3) 0.18112(17) 0.11507(16) 0.0772(7) Uani 1 1 d . . . . . H7 H -0.555(5) 0.101(4) 0.109(3) 0.131(14) Uiso 1 1 d . . . . . O8 O -0.3295(3) 0.19727(15) 0.23818(14) 0.0710(6) Uani 1 1 d . . . . . O9 O -0.1309(2) 0.60353(16) 0.38814(13) 0.0580(5) Uani 1 1 d . . . . . H9A H -0.137(4) 0.675(3) 0.400(2) 0.106(13) Uiso 1 1 d . . . . . C22 C -0.4231(3) 0.2386(2) 0.18984(19) 0.0482(6) Uani 1 1 d . . . . . C23 C -0.4035(3) 0.35943(19) 0.20734(17) 0.0418(6) Uani 1 1 d . . . . . C24 C -0.2801(3) 0.42771(19) 0.28844(16) 0.0404(5) Uani 1 1 d . . . . . H24 H -0.213411 0.397654 0.330081 0.048 Uiso 1 1 calc R . . . . C25 C -0.2556(3) 0.54051(19) 0.30773(17) 0.0405(6) Uani 1 1 d . . . . . C26 C -0.3543(3) 0.5846(2) 0.24505(18) 0.0461(6) Uani 1 1 d . . . . . H26 H -0.337654 0.660361 0.257236 0.055 Uiso 1 1 calc R . . . . C27 C -0.4775(3) 0.5160(2) 0.16441(18) 0.0533(7) Uani 1 1 d . . . . . H27 H -0.544002 0.545956 0.122612 0.064 Uiso 1 1 calc R . . . . C28 C -0.5027(3) 0.4037(2) 0.14531(18) 0.0512(7) Uani 1 1 d . . . . . H28 H -0.586050 0.357952 0.090950 0.061 Uiso 1 1 calc R . . . . O10 O -0.4020(3) 0.03007(16) -0.08080(16) 0.0830(7) Uani 1 1 d . . . . . H10A H -0.320529 0.068852 -0.032196 0.124 Uiso 1 1 d G . . . . H10B H -0.410892 0.067875 -0.118717 0.124 Uiso 1 1 d G . . . . O11 O -0.4288(3) 0.1639(3) -0.18928(15) 0.0979(9) Uani 1 1 d . . . . . H11A H -0.339450 0.184507 -0.204798 0.147 Uiso 1 1 d G . . . . H11B H -0.511141 0.146348 -0.240254 0.147 Uiso 1 1 d G . . . . 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 0.0536(10) 0.0291(9) 0.0656(12) 0.0098(8) 0.0073(9) 0.0060(8) O2 0.0674(12) 0.0395(10) 0.0604(12) 0.0226(9) -0.0018(9) 0.0126(9) O3 0.0577(10) 0.0418(9) 0.0386(10) 0.0178(8) -0.0037(8) 0.0087(8) N1 0.0352(10) 0.0355(10) 0.0427(11) 0.0189(9) 0.0154(8) 0.0102(8) N2 0.0476(11) 0.0274(10) 0.0364(11) 0.0125(8) 0.0048(9) -0.0011(9) N3 0.0531(12) 0.0281(10) 0.0288(10) 0.0096(8) 0.0032(9) 0.0007(9) N4 0.0367(10) 0.0271(9) 0.0322(10) 0.0114(8) 0.0061(8) 0.0035(8) N5 0.0335(9) 0.0280(9) 0.0299(10) 0.0072(8) 0.0033(8) 0.0025(8) C1 0.0387(12) 0.0283(12) 0.0453(14) 0.0106(10) 0.0019(10) 0.0044(10) C2 0.0587(15) 0.0253(11) 0.0355(13) 0.0104(9) 0.0087(11) 0.0062(11) C3 0.0531(14) 0.0320(12) 0.0339(13) 0.0107(10) 0.0026(11) 0.0071(11) C4 0.0396(13) 0.0332(12) 0.0512(15) 0.0200(11) 0.0000(11) 0.0034(10) C5 0.0401(12) 0.0291(11) 0.0306(12) 0.0118(9) 0.0118(10) 0.0016(10) C6 0.0470(13) 0.0356(12) 0.0270(12) 0.0111(10) 0.0027(10) 0.0018(11) C7 0.0360(11) 0.0291(11) 0.0259(11) 0.0087(9) 0.0078(9) 0.0017(9) C8 0.0311(11) 0.0274(11) 0.0274(11) 0.0078(9) 0.0093(9) 0.0028(9) C9 0.0362(12) 0.0260(11) 0.0347(12) 0.0053(9) 0.0116(10) 0.0030(9) C10 0.0355(11) 0.0283(11) 0.0321(12) 0.0098(9) 0.0108(9) 0.0065(9) C11 0.0388(12) 0.0328(12) 0.0283(12) 0.0101(9) 0.0090(10) 0.0056(10) C12 0.0433(13) 0.0330(13) 0.0454(14) 0.0130(11) 0.0161(11) 0.0100(11) C13 0.0355(12) 0.0355(12) 0.0401(14) 0.0100(10) -0.0032(10) 0.0056(10) C14 0.0613(16) 0.0547(16) 0.0376(15) 0.0173(12) 0.0047(12) 0.0145(13) O4 0.0287(8) 0.0643(12) 0.0704(12) 0.0387(10) 0.0194(8) 0.0192(8) O5 0.0347(9) 0.0811(13) 0.0501(11) 0.0365(10) 0.0162(8) 0.0102(9) O6 0.0241(8) 0.0459(10) 0.0601(11) 0.0150(8) 0.0106(7) 0.0087(7) C15 0.0282(11) 0.0349(12) 0.0343(13) 0.0056(10) 0.0079(9) 0.0045(10) C16 0.0246(10) 0.0311(11) 0.0273(11) 0.0074(9) 0.0034(8) 0.0021(9) C17 0.0289(11) 0.0377(12) 0.0425(13) 0.0178(10) 0.0049(10) 0.0102(10) C18 0.0414(13) 0.0467(14) 0.0476(15) 0.0287(12) 0.0110(11) 0.0065(11) C19 0.0287(11) 0.0486(14) 0.0420(14) 0.0186(11) 0.0136(10) 0.0039(10) C20 0.0235(10) 0.0352(12) 0.0342(12) 0.0102(9) 0.0049(9) 0.0056(9) C21 0.0296(11) 0.0341(12) 0.0366(13) 0.0177(10) 0.0079(9) 0.0067(10) O7 0.0722(14) 0.0436(12) 0.0885(16) 0.0076(11) -0.0070(11) -0.0004(11) O8 0.0882(15) 0.0442(11) 0.0714(14) 0.0148(10) 0.0070(11) 0.0177(11) O9 0.0594(12) 0.0419(11) 0.0576(12) 0.0100(9) -0.0052(9) 0.0099(9) C22 0.0480(15) 0.0445(15) 0.0509(16) 0.0095(13) 0.0180(13) 0.0098(13) C23 0.0396(13) 0.0407(14) 0.0468(15) 0.0111(11) 0.0187(11) 0.0067(11) C24 0.0389(13) 0.0416(13) 0.0454(14) 0.0170(11) 0.0143(11) 0.0132(11) C25 0.0369(12) 0.0408(14) 0.0424(14) 0.0109(11) 0.0115(11) 0.0071(11) C26 0.0499(14) 0.0357(13) 0.0535(16) 0.0154(12) 0.0134(12) 0.0101(12) C27 0.0518(15) 0.0548(16) 0.0512(16) 0.0214(13) 0.0037(12) 0.0134(13) C28 0.0465(15) 0.0499(16) 0.0469(16) 0.0069(12) 0.0058(12) 0.0049(13) O10 0.0934(16) 0.0442(12) 0.0754(15) 0.0111(10) -0.0250(12) -0.0064(11) O11 0.0640(13) 0.158(2) 0.0677(15) 0.0579(16) 0.0016(11) -0.0144(16) 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' 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 C12 O2 H2 109.5 . . ? H1A N1 H1B 107.9 . . ? C1 N1 H1A 109.2 . . ? C1 N1 H1B 109.2 . . ? C1 N1 C3 112.10(16) . . ? C3 N1 H1A 109.2 . . ? C3 N1 H1B 109.2 . . ? C4 N2 C2 112.32(17) . . ? C5 N2 C2 124.04(19) . . ? C5 N2 C4 120.93(18) . . ? C6 N3 C5 115.49(18) . . ? C8 N4 C5 116.35(18) . . ? C8 N5 C13 120.32(17) . . ? C9 N5 C8 119.20(18) . . ? C9 N5 C13 120.48(17) . . ? N1 C1 H1C 109.7 . . ? N1 C1 H1D 109.7 . . ? N1 C1 C2 109.85(17) . . ? H1C C1 H1D 108.2 . . ? C2 C1 H1C 109.7 . . ? C2 C1 H1D 109.7 . . ? N2 C2 C1 109.94(18) . . ? N2 C2 H2A 109.7 . . ? N2 C2 H2B 109.7 . . ? C1 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? N1 C3 H3A 109.8 . . ? N1 C3 H3B 109.8 . . ? N1 C3 C4 109.17(18) . . ? H3A C3 H3B 108.3 . . ? C4 C3 H3A 109.8 . . ? C4 C3 H3B 109.8 . . ? N2 C4 C3 109.18(18) . . ? N2 C4 H4A 109.8 . . ? N2 C4 H4B 109.8 . . ? C3 C4 H4A 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? N2 C5 N3 116.85(19) . . ? N4 C5 N2 117.45(19) . . ? N4 C5 N3 125.7(2) . . ? N3 C6 H6 117.9 . . ? N3 C6 C7 124.3(2) . . ? C7 C6 H6 117.9 . . ? C6 C7 C8 114.91(19) . . ? C6 C7 C11 123.34(19) . . ? C8 C7 C11 121.73(18) . . ? N4 C8 N5 117.09(18) . . ? N4 C8 C7 123.24(18) . . ? N5 C8 C7 119.67(19) . . ? N5 C9 H9 118.0 . . ? N5 C9 C10 124.04(19) . . ? C10 C9 H9 118.0 . . ? C9 C10 C11 120.1(2) . . ? C9 C10 C12 119.56(19) . . ? C11 C10 C12 120.3(2) . . ? O3 C11 C7 122.62(19) . . ? O3 C11 C10 122.2(2) . . ? C7 C11 C10 115.22(19) . . ? O1 C12 O2 120.7(2) . . ? O1 C12 C10 123.2(2) . . ? O2 C12 C10 116.1(2) . . ? N5 C13 H13A 109.1 . . ? N5 C13 H13B 109.1 . . ? N5 C13 C14 112.30(18) . . ? H13A C13 H13B 107.9 . . ? C14 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 O4 H4 109.5 . . ? O5 C15 O6 124.0(2) . . ? O5 C15 C16 118.26(19) . . ? O6 C15 C16 117.8(2) . . ? C17 C16 C15 120.45(19) . . ? C21 C16 C15 120.30(19) . . ? C21 C16 C17 119.25(19) . . ? C16 C17 H17 120.2 . . ? C18 C17 C16 119.7(2) . . ? C18 C17 H17 120.2 . . ? C17 C18 H18 119.5 . . ? C19 C18 C17 121.0(2) . . ? C19 C18 H18 119.5 . . ? C18 C19 H19 120.1 . . ? C18 C19 C20 119.7(2) . . ? C20 C19 H19 120.1 . . ? O4 C20 C19 123.21(18) . . ? O4 C20 C21 117.23(19) . . ? C19 C20 C21 119.5(2) . . ? C16 C21 C20 120.8(2) . . ? C16 C21 H21 121.0(12) . . ? C20 C21 H21 118.1(12) . . ? C22 O7 H7 107(2) . . ? C25 O9 H9A 111(2) . . ? O7 C22 C23 113.2(2) . . ? O8 C22 O7 123.2(2) . . ? O8 C22 C23 123.6(2) . . ? C24 C23 C22 117.8(2) . . ? C28 C23 C22 122.1(2) . . ? C28 C23 C24 120.1(2) . . ? C23 C24 H24 119.9 . . ? C25 C24 C23 120.2(2) . . ? C25 C24 H24 119.9 . . ? O9 C25 C24 117.6(2) . . ? O9 C25 C26 122.9(2) . . ? C24 C25 C26 119.6(2) . . ? C25 C26 H26 120.0 . . ? C27 C26 C25 119.9(2) . . ? C27 C26 H26 120.0 . . ? C26 C27 H27 119.7 . . ? C28 C27 C26 120.6(2) . . ? C28 C27 H27 119.7 . . ? C23 C28 H28 120.2 . . ? C27 C28 C23 119.6(2) . . ? C27 C28 H28 120.2 . . ? H10A O10 H10B 104.5 . . ? H11A O11 H11B 104.5 . . ? 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 O1 C12 1.224(3) . ? O2 H2 0.8200 . ? O2 C12 1.311(3) . ? O3 C11 1.264(2) . ? N1 H1A 0.8900 . ? N1 H1B 0.8900 . ? N1 C1 1.486(3) . ? N1 C3 1.489(3) . ? N2 C2 1.461(3) . ? N2 C4 1.453(3) . ? N2 C5 1.345(3) . ? N3 C5 1.370(3) . ? N3 C6 1.312(3) . ? N4 C5 1.337(2) . ? N4 C8 1.329(3) . ? N5 C8 1.386(2) . ? N5 C9 1.345(3) . ? N5 C13 1.484(3) . ? C1 H1C 0.9700 . ? C1 H1D 0.9700 . ? C1 C2 1.511(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.506(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 H6 0.9300 . ? C6 C7 1.394(3) . ? C7 C8 1.396(3) . ? C7 C11 1.433(3) . ? C9 H9 0.9300 . ? C9 C10 1.358(3) . ? C10 C11 1.438(3) . ? C10 C12 1.468(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.502(3) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? O4 H4 0.8200 . ? O4 C20 1.358(2) . ? O5 C15 1.251(3) . ? O6 C15 1.264(2) . ? C15 C16 1.500(3) . ? C16 C17 1.391(3) . ? C16 C21 1.383(3) . ? C17 H17 0.9300 . ? C17 C18 1.378(3) . ? C18 H18 0.9300 . ? C18 C19 1.376(3) . ? C19 H19 0.9300 . ? C19 C20 1.383(3) . ? C20 C21 1.386(3) . ? C21 H21 0.96(2) . ? O7 H7 1.01(4) . ? O7 C22 1.318(3) . ? O8 C22 1.202(3) . ? O9 H9A 0.90(4) . ? O9 C25 1.364(3) . ? C22 C23 1.489(3) . ? C23 C24 1.384(3) . ? C23 C28 1.381(3) . ? C24 H24 0.9300 . ? C24 C25 1.383(3) . ? C25 C26 1.384(3) . ? C26 H26 0.9300 . ? C26 C27 1.381(3) . ? C27 H27 0.9300 . ? C27 C28 1.377(4) . ? C28 H28 0.9300 . ? O10 H10A 0.8504 . ? O10 H10B 0.8498 . ? O11 H11A 0.8500 . ? O11 H11B 0.8499 . ? 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 N1 C1 C2 N2 -54.7(2) . . . . ? N1 C3 C4 N2 58.2(2) . . . . ? N3 C6 C7 C8 -0.8(3) . . . . ? N3 C6 C7 C11 -179.2(2) . . . . ? N5 C9 C10 C11 0.0(3) . . . . ? N5 C9 C10 C12 -179.99(19) . . . . ? C1 N1 C3 C4 -57.0(2) . . . . ? C2 N2 C4 C3 -60.9(2) . . . . ? C2 N2 C5 N3 -10.7(3) . . . . ? C2 N2 C5 N4 169.28(19) . . . . ? C3 N1 C1 C2 55.3(2) . . . . ? C4 N2 C2 C1 59.1(2) . . . . ? C4 N2 C5 N3 -170.57(19) . . . . ? C4 N2 C5 N4 9.4(3) . . . . ? C5 N2 C2 C1 -102.3(2) . . . . ? C5 N2 C4 C3 101.2(2) . . . . ? C5 N3 C6 C7 -0.9(3) . . . . ? C5 N4 C8 N5 179.27(17) . . . . ? C5 N4 C8 C7 -0.2(3) . . . . ? C6 N3 C5 N2 -177.78(19) . . . . ? C6 N3 C5 N4 2.3(3) . . . . ? C6 C7 C8 N4 1.3(3) . . . . ? C6 C7 C8 N5 -178.09(18) . . . . ? C6 C7 C11 O3 -0.9(3) . . . . ? C6 C7 C11 C10 178.7(2) . . . . ? C8 N4 C5 N2 178.28(18) . . . . ? C8 N4 C5 N3 -1.7(3) . . . . ? C8 N5 C9 C10 0.8(3) . . . . ? C8 N5 C13 C14 -80.0(2) . . . . ? C8 C7 C11 O3 -179.2(2) . . . . ? C8 C7 C11 C10 0.4(3) . . . . ? C9 N5 C8 N4 179.58(18) . . . . ? C9 N5 C8 C7 -0.9(3) . . . . ? C9 N5 C13 C14 99.9(2) . . . . ? C9 C10 C11 O3 179.0(2) . . . . ? C9 C10 C11 C7 -0.6(3) . . . . ? C9 C10 C12 O1 4.9(3) . . . . ? C9 C10 C12 O2 -174.5(2) . . . . ? C11 C7 C8 N4 179.76(19) . . . . ? C11 C7 C8 N5 0.3(3) . . . . ? C11 C10 C12 O1 -175.1(2) . . . . ? C11 C10 C12 O2 5.5(3) . . . . ? C12 C10 C11 O3 -1.0(3) . . . . ? C12 C10 C11 C7 179.38(19) . . . . ? C13 N5 C8 N4 -0.5(3) . . . . ? C13 N5 C8 C7 178.94(19) . . . . ? C13 N5 C9 C10 -179.09(19) . . . . ? O4 C20 C21 C16 -179.13(19) . . . . ? O5 C15 C16 C17 -171.5(2) . . . . ? O5 C15 C16 C21 8.4(3) . . . . ? O6 C15 C16 C17 8.2(3) . . . . ? O6 C15 C16 C21 -171.91(19) . . . . ? C15 C16 C17 C18 -179.44(19) . . . . ? C15 C16 C21 C20 -179.99(19) . . . . ? C16 C17 C18 C19 -0.7(3) . . . . ? C17 C16 C21 C20 -0.1(3) . . . . ? C17 C18 C19 C20 0.1(3) . . . . ? C18 C19 C20 O4 179.1(2) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? C19 C20 C21 C16 -0.5(3) . . . . ? C21 C16 C17 C18 0.7(3) . . . . ? O7 C22 C23 C24 175.0(2) . . . . ? O7 C22 C23 C28 -5.5(3) . . . . ? O8 C22 C23 C24 -5.8(4) . . . . ? O8 C22 C23 C28 173.7(3) . . . . ? O9 C25 C26 C27 179.4(2) . . . . ? C22 C23 C24 C25 179.5(2) . . . . ? C22 C23 C28 C27 -179.2(2) . . . . ? C23 C24 C25 O9 -179.3(2) . . . . ? C23 C24 C25 C26 -0.5(3) . . . . ? C24 C23 C28 C27 0.3(4) . . . . ? C24 C25 C26 C27 0.7(4) . . . . ? C25 C26 C27 C28 -0.3(4) . . . . ? C26 C27 C28 C23 -0.2(4) . . . . ? C28 C23 C24 C25 0.0(3) . . . . ?