#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:42:52 +0300 (Fri, 01 May 2020) $ #$Revision: 251338 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240433.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_7240433 loop_ _publ_author_name 'Shi, Zhi-Ping' 'Ren, Guo-Bin' 'Qi, Ming-Hui' 'Li, Zhong' 'Xu, Xiaoyong' _publ_section_title ; Design, screening, and properties of novel solvates of azoxystrobin based on isomorphism ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00204F _journal_year 2020 _chemical_formula_sum 'C26 H21 N3 O6' _chemical_formula_weight 471.46 _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_update_record ; 2019-09-06 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.463(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.3314(6) _cell_length_b 7.8730(4) _cell_length_c 24.6987(11) _cell_measurement_reflns_used 5782 _cell_measurement_temperature 298.(2) _cell_measurement_theta_max 66.4394 _cell_measurement_theta_min 3.6284 _cell_volume 2365.2(2) _computing_cell_refinement 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_molecular_graphics 'shelXle (C.B. Huebschle, rev 882)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 298.(2) _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 quest' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_unetI/netI 0.0506 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 15668 _diffrn_reflns_theta_full 66.66 _diffrn_reflns_theta_max 66.66 _diffrn_reflns_theta_min 3.63 _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_T_max 0.91 _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 984 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.192 _refine_diff_density_min -0.135 _refine_ls_extinction_coef 0.0042(3) _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)' _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 365 _refine_ls_number_reflns 4182 _refine_ls_number_restraints 203 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0505 _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^)+(0.0583P)^2^+0.3313P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1269 _refine_ls_wR_factor_ref 0.1419 _reflns_number_gt 2982 _reflns_number_total 4182 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00204f2.cif _cod_data_source_block SC250_SZP_18_1 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was changed to 'multi-scan' 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 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7240433 _shelx_res_file ; TITL SC250_SZP_18_1_0m_a.res in P2(1)/n SC250_SZP_18_1_0m_a.res created by SHELXL-2017/1 at 12:24:59 on 23-May-2019 REM Old TITL SC250_SZP_18_1_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.167, Rweak 0.012, Alpha 0.046, Orientation as input REM Formula found by SHELXT: C27 N3 O5 CELL 1.54178 12.3314 7.8730 24.6987 90.000 99.463 90.000 ZERR 4.000 0.0006 0.0004 0.0011 0.000 0.002 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 104 84 12 24 TEMP 25 SIZE 0.12 0.13 0.32 L.S. 10 BOND $H LIST 4 acta htab EQIV $1 x, y-1, z HTAB C9 O3 EQIV $2 x, y+1, z HTAB C21 O2_$2 EQIV $3 -x+1/2, y+1/2, -z+3/2 HTAB C21 O5_$3 EQIV $4 -x+1/2, y-1/2, -z+3/2 HTAB C22 O5_$4 conf FMAP 2 PLAN 10 sadi o6 c23 o6 c26 sadi o6 c24 o6 c25 sadi c23 c24 c24 c25 c25 c26 simu 0.02 o6 > c26a delu 0.02 o6 > c26a WGHT 0.058300 0.331300 EXTI 0.004228 FVAR 0.56177 0.45853 PART 1 21.0000 O6 4 0.345466 -0.072022 0.882966 21.00000 0.13297 0.15669 = 0.12170 -0.00917 0.04100 0.00059 C23 1 0.392741 -0.187003 0.852808 21.00000 0.11419 0.10637 = 0.10257 -0.00690 0.04682 -0.00209 AFIX 43 H23 2 0.356826 -0.248954 0.823120 21.00000 -1.20000 AFIX 0 C24 1 0.503846 -0.195324 0.874200 21.00000 0.12337 0.12345 = 0.12757 0.00361 0.04710 0.01295 AFIX 43 H24 2 0.557092 -0.254603 0.859254 21.00000 -1.20000 AFIX 0 C25 1 0.520773 -0.101789 0.920664 21.00000 0.13487 0.13792 = 0.11308 0.00349 0.00485 0.02693 AFIX 43 H25 2 0.586761 -0.092666 0.944876 21.00000 -1.20000 AFIX 0 C26 1 0.426459 -0.024502 0.925929 21.00000 0.13004 0.14006 = 0.09186 -0.02103 0.01901 -0.00196 AFIX 43 H26 2 0.416824 0.049607 0.954073 21.00000 -1.20000 AFIX 0 PART 2 -21.00000 same o6 > c26 O6A 4 0.469767 -0.226455 0.871326 -21.00000 0.15769 0.13188 = 0.16267 0.00579 0.01203 0.01906 C23A 1 0.529747 -0.130674 0.910581 -21.00000 0.13126 0.13643 = 0.09782 0.01669 0.00213 0.01170 AFIX 43 H23A 2 0.602844 -0.150830 0.925560 -21.00000 -1.20000 AFIX 0 C24A 1 0.468861 -0.002187 0.924917 -21.00000 0.13484 0.12349 = 0.09239 0.00813 0.01564 -0.01117 AFIX 43 H24A 2 0.495036 0.082205 0.950043 -21.00000 -1.20000 AFIX 0 C25A 1 0.365169 -0.011735 0.898157 -21.00000 0.12905 0.12675 = 0.12733 0.00120 0.03698 -0.00827 AFIX 43 H25A 2 0.306182 0.058750 0.901628 -21.00000 -1.20000 AFIX 0 C26A 1 0.366674 -0.153654 0.863566 -21.00000 0.12979 0.12448 = 0.13152 -0.00519 0.03136 -0.00408 AFIX 43 H26A 2 0.306598 -0.192750 0.838959 -21.00000 -1.20000 AFIX 0 PART 0 O1 4 0.389960 0.862393 0.518085 11.00000 0.07195 0.04781 = 0.06105 0.00466 -0.01027 -0.00489 N1 3 0.131615 0.912170 0.559103 11.00000 0.10860 0.15134 = 0.10156 0.01106 0.04722 -0.00299 C1 1 0.169964 0.937771 0.521072 11.00000 0.07217 0.09075 = 0.08844 0.00688 0.02148 -0.00057 C2 1 0.216630 0.969279 0.472745 11.00000 0.06112 0.06015 = 0.07103 0.00668 0.01021 -0.00455 N2 3 0.324542 0.592859 0.494381 11.00000 0.06542 0.05439 = 0.05798 -0.00254 -0.00465 -0.00667 O2 4 0.509102 0.390526 0.629942 11.00000 0.06081 0.04562 = 0.05484 0.00395 -0.00145 -0.00729 O3 4 0.451011 0.879934 0.678695 11.00000 0.07284 0.05320 = 0.09130 0.01060 0.03189 0.00405 N3 3 0.388551 0.359771 0.552639 11.00000 0.06686 0.04775 = 0.06229 -0.00281 -0.00179 -0.00827 C3 1 0.153779 1.040392 0.426168 11.00000 0.05893 0.07553 = 0.09188 0.01575 0.00149 0.00322 AFIX 43 H3 2 0.080899 1.070324 0.426394 11.00000 -1.20000 AFIX 0 O4 4 0.469716 0.356112 0.765773 11.00000 0.05224 0.06966 = 0.08850 0.02588 0.01555 0.00056 C4 1 0.200077 1.065849 0.380107 11.00000 0.07551 0.07272 = 0.07961 0.02595 -0.00903 -0.00925 AFIX 43 H4 2 0.157911 1.111349 0.348785 11.00000 -1.20000 AFIX 0 O5 4 0.309731 0.491870 0.754394 11.00000 0.05685 0.08280 = 0.10730 0.02713 0.02887 0.00568 C5 1 0.307638 1.025057 0.379707 11.00000 0.08005 0.07902 = 0.06088 0.01048 0.00614 -0.01641 AFIX 43 H5 2 0.338492 1.045571 0.348415 11.00000 -1.20000 AFIX 0 C6 1 0.370689 0.953937 0.425160 11.00000 0.05771 0.06046 = 0.06649 0.00004 0.00675 -0.00546 AFIX 43 H6 2 0.443750 0.925564 0.424725 11.00000 -1.20000 AFIX 0 C7 1 0.324315 0.925470 0.471107 11.00000 0.05639 0.04512 = 0.05676 0.00402 0.00019 -0.00431 C8 1 0.389311 0.692452 0.528272 11.00000 0.05356 0.04522 = 0.04975 -0.00007 0.00583 -0.00318 C9 1 0.457453 0.637497 0.574512 11.00000 0.05353 0.05007 = 0.04930 -0.00215 0.00328 -0.00709 AFIX 43 H9 2 0.504045 0.710532 0.597026 11.00000 -1.20000 AFIX 0 C10 1 0.451880 0.467542 0.585086 11.00000 0.04833 0.04625 = 0.04847 -0.00194 0.00665 -0.00322 C11 1 0.329311 0.429988 0.509019 11.00000 0.07667 0.05623 = 0.06387 -0.00735 -0.00845 -0.01291 AFIX 43 H11 2 0.285287 0.356286 0.485510 11.00000 -1.20000 AFIX 0 C12 1 0.594216 0.480766 0.662392 11.00000 0.04970 0.04279 = 0.04965 0.00441 0.00318 -0.00554 C13 1 0.698478 0.458865 0.650876 11.00000 0.05958 0.05440 = 0.06088 0.00218 0.01461 -0.00012 AFIX 43 H13 2 0.710138 0.393700 0.620956 11.00000 -1.20000 AFIX 0 C14 1 0.785365 0.534424 0.684105 11.00000 0.04991 0.06507 = 0.08017 0.01172 0.01198 -0.00232 AFIX 43 H14 2 0.856468 0.520121 0.676871 11.00000 -1.20000 AFIX 0 C15 1 0.767118 0.631518 0.728207 11.00000 0.05337 0.07030 = 0.06615 0.00679 -0.00294 -0.01434 AFIX 43 H15 2 0.825887 0.682405 0.750836 11.00000 -1.20000 AFIX 0 C16 1 0.662151 0.652833 0.738605 11.00000 0.06238 0.06164 = 0.05394 -0.00316 0.00405 -0.00905 AFIX 43 H16 2 0.650776 0.718743 0.768413 11.00000 -1.20000 AFIX 0 C17 1 0.572257 0.578577 0.705792 11.00000 0.05137 0.04680 = 0.05193 0.00450 0.00687 -0.00415 C18 1 0.458854 0.608456 0.716617 11.00000 0.05315 0.05355 = 0.05794 0.00030 0.01163 -0.00336 C19 1 0.405924 0.754089 0.703269 11.00000 0.05868 0.05609 = 0.06794 0.00142 0.02034 -0.00136 AFIX 43 H19 2 0.335440 0.768087 0.711376 11.00000 -1.20000 AFIX 0 C20 1 0.403374 0.483085 0.746567 11.00000 0.05017 0.05871 = 0.06347 0.00446 0.01068 -0.00140 C21 1 0.380482 1.020507 0.659787 11.00000 0.09997 0.05716 = 0.09606 0.01343 0.03905 0.01526 AFIX 137 H21A 2 0.348227 1.002512 0.622132 11.00000 -1.50000 H21B 2 0.422733 1.123490 0.662820 11.00000 -1.50000 H21C 2 0.323380 1.029412 0.681781 11.00000 -1.50000 AFIX 0 C22 1 0.422979 0.234428 0.799560 11.00000 0.06506 0.08986 = 0.12247 0.05130 0.01835 0.00031 AFIX 137 H22A 2 0.357098 0.187091 0.778973 11.00000 -1.50000 H22B 2 0.405831 0.290459 0.831626 11.00000 -1.50000 H22C 2 0.475079 0.145210 0.810441 11.00000 -1.50000 AFIX 0 HKLF 4 REM SC250_SZP_18_1_0m_a.res in P2(1)/n REM R1 = 0.0505 for 2982 Fo > 4sig(Fo) and 0.0719 for all 4182 data REM 365 parameters refined using 203 restraints END WGHT 0.0583 0.3313 REM Instructions for potential hydrogen bonds HTAB C23^a O5_$1 HTAB C9 O3 HTAB C21 O2_$2 HTAB C21 O5_$3 HTAB C22 O5_$4 REM Highest difference peak 0.192, deepest hole -0.135, 1-sigma level 0.033 Q1 1 0.4553 -0.1540 0.9386 11.00000 0.05 0.19 Q2 1 0.4097 1.0793 0.6263 11.00000 0.05 0.18 Q3 1 0.4894 0.2081 0.8325 11.00000 0.05 0.15 Q4 1 0.3712 -0.1838 0.9148 11.00000 0.05 0.15 Q5 1 0.2894 0.9805 0.6491 11.00000 0.05 0.15 Q6 1 0.4638 0.0831 0.7712 11.00000 0.05 0.14 Q7 1 0.4898 -0.2524 0.9210 11.00000 0.05 0.13 Q8 1 0.3774 -0.2547 0.8884 11.00000 0.05 0.13 Q9 1 0.4380 1.0271 0.6912 11.00000 0.05 0.13 Q10 1 0.4354 0.5616 0.7312 11.00000 0.05 0.12 ; _shelx_res_checksum 24024 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_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O6 0.3455(10) -0.072(2) 0.8830(5) 0.135(3) Uani d U P D 0.459(17) A 1 C C23 0.3927(13) -0.187(2) 0.8528(6) 0.104(3) Uani d U P D 0.459(17) A 1 H H23 0.356826 -0.248954 0.82312 0.125 Uiso calc U P R 0.459(17) A 1 C C24 0.5038(14) -0.195(3) 0.8742(9) 0.122(4) Uani d U P D 0.459(17) A 1 H H24 0.557092 -0.254603 0.859254 0.146 Uiso calc U P R 0.459(17) A 1 C C25 0.5208(15) -0.102(4) 0.9207(9) 0.130(4) Uani d U P D 0.459(17) A 1 H H25 0.586761 -0.092666 0.944876 0.156 Uiso calc U P R 0.459(17) A 1 C C26 0.4265(16) -0.025(2) 0.9259(7) 0.121(4) Uani d U P D 0.459(17) A 1 H H26 0.416824 0.049607 0.954073 0.145 Uiso calc U P R 0.459(17) A 1 O O6A 0.4698(12) -0.2265(17) 0.8713(6) 0.152(4) Uani d U P D 0.541(17) A 2 C C23A 0.5297(13) -0.131(3) 0.9106(8) 0.124(3) Uani d U P D 0.541(17) A 2 H H23A 0.602844 -0.15083 0.92556 0.148 Uiso calc U P R 0.541(17) A 2 C C24A 0.4689(14) -0.0022(19) 0.9249(6) 0.117(3) Uani d U P D 0.541(17) A 2 H H24A 0.495036 0.082205 0.950043 0.141 Uiso calc U P R 0.541(17) A 2 C C25A 0.3652(14) -0.012(2) 0.8982(8) 0.126(3) Uani d U P D 0.541(17) A 2 H H25A 0.306182 0.05875 0.901628 0.151 Uiso calc U P R 0.541(17) A 2 C C26A 0.3667(12) -0.154(2) 0.8636(7) 0.127(4) Uani d U P D 0.541(17) A 2 H H26A 0.306598 -0.19275 0.838959 0.153 Uiso calc U P R 0.541(17) A 2 O O1 0.38996(15) 0.8624(2) 0.51809(6) 0.0627(4) Uani d . . . 1.0 . . N N1 0.1316(3) 0.9122(5) 0.55910(13) 0.1171(11) Uani d . . . 1.0 . . C C1 0.1700(3) 0.9378(5) 0.52107(13) 0.0829(8) Uani d . . . 1.0 . . C C2 0.2166(2) 0.9693(3) 0.47274(11) 0.0642(6) Uani d . . . 1.0 . . N N2 0.32454(18) 0.5929(3) 0.49438(8) 0.0609(5) Uani d . . . 1.0 . . O O2 0.50910(13) 0.39053(19) 0.62994(6) 0.0550(4) Uani d . . . 1.0 . . O O3 0.45101(16) 0.8799(2) 0.67869(8) 0.0704(5) Uani d . . . 1.0 . . N N3 0.38855(18) 0.3598(2) 0.55264(8) 0.0604(5) Uani d . . . 1.0 . . C C3 0.1538(2) 1.0404(4) 0.42617(13) 0.0767(8) Uani d . . . 1.0 . . H H3 0.080899 1.070324 0.426394 0.092 Uiso calc U . R 1.0 . . O O4 0.46972(14) 0.3561(2) 0.76577(8) 0.0697(5) Uani d . . . 1.0 . . C C4 0.2001(3) 1.0658(4) 0.38011(12) 0.0784(8) Uani d . . . 1.0 . . H H4 0.157911 1.111349 0.348785 0.094 Uiso calc U . R 1.0 . . O O5 0.30973(15) 0.4919(3) 0.75439(9) 0.0806(6) Uani d . . . 1.0 . . C C5 0.3076(3) 1.0251(4) 0.37971(11) 0.0739(7) Uani d . . . 1.0 . . H H5 0.338492 1.045571 0.348415 0.089 Uiso calc U . R 1.0 . . C C6 0.3707(2) 0.9539(3) 0.42516(10) 0.0619(6) Uani d . . . 1.0 . . H H6 0.44375 0.925564 0.424725 0.074 Uiso calc U . R 1.0 . . C C7 0.3243(2) 0.9255(3) 0.47111(9) 0.0538(5) Uani d . . . 1.0 . . C C8 0.38931(18) 0.6925(3) 0.52827(8) 0.0498(5) Uani d . . . 1.0 . . C C9 0.45745(19) 0.6375(3) 0.57451(8) 0.0515(5) Uani d . . . 1.0 . . H H9 0.504045 0.710532 0.597026 0.062 Uiso calc U . R 1.0 . . C C10 0.45188(18) 0.4675(3) 0.58509(8) 0.0478(5) Uani d . . . 1.0 . . C C11 0.3293(2) 0.4300(3) 0.50902(10) 0.0678(7) Uani d . . . 1.0 . . H H11 0.285287 0.356286 0.48551 0.081 Uiso calc U . R 1.0 . . C C12 0.59422(18) 0.4808(3) 0.66239(8) 0.0479(5) Uani d . . . 1.0 . . C C13 0.6985(2) 0.4589(3) 0.65088(10) 0.0578(6) Uani d . . . 1.0 . . H H13 0.710138 0.3937 0.620956 0.069 Uiso calc U . R 1.0 . . C C14 0.7854(2) 0.5344(3) 0.68411(11) 0.0649(6) Uani d . . . 1.0 . . H H14 0.856468 0.520121 0.676871 0.078 Uiso calc U . R 1.0 . . C C15 0.7671(2) 0.6315(3) 0.72821(10) 0.0647(6) Uani d . . . 1.0 . . H H15 0.825887 0.682405 0.750836 0.078 Uiso calc U . R 1.0 . . C C16 0.6622(2) 0.6528(3) 0.73861(9) 0.0599(6) Uani d . . . 1.0 . . H H16 0.650776 0.718743 0.768413 0.072 Uiso calc U . R 1.0 . . C C17 0.57226(18) 0.5786(3) 0.70579(8) 0.0502(5) Uani d . . . 1.0 . . C C18 0.4589(2) 0.6085(3) 0.71662(9) 0.0546(5) Uani d . . . 1.0 . . C C19 0.4059(2) 0.7541(3) 0.70327(10) 0.0598(6) Uani d . . . 1.0 . . H H19 0.33544 0.768087 0.711376 0.072 Uiso calc U . R 1.0 . . C C20 0.4034(2) 0.4831(3) 0.74657(10) 0.0573(6) Uani d . . . 1.0 . . C C21 0.3805(3) 1.0205(4) 0.65979(13) 0.0818(9) Uani d . . . 1.0 . . H H21A 0.348227 1.002512 0.622132 0.123 Uiso calc U . R 1.0 . . H H21B 0.422733 1.12349 0.66282 0.123 Uiso calc U . R 1.0 . . H H21C 0.32338 1.029412 0.681781 0.123 Uiso calc U . R 1.0 . . C C22 0.4230(3) 0.2344(4) 0.79956(15) 0.0921(10) Uani d . . . 1.0 . . H H22A 0.357098 0.187091 0.778973 0.138 Uiso calc U . R 1.0 . . H H22B 0.405831 0.290459 0.831626 0.138 Uiso calc U . R 1.0 . . H H22C 0.475079 0.14521 0.810441 0.138 Uiso calc U . R 1.0 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O6 0.133(6) 0.157(9) 0.122(7) 0.001(6) 0.041(4) -0.009(6) C23 0.114(7) 0.106(7) 0.103(5) -0.002(6) 0.047(5) -0.007(5) C24 0.123(7) 0.123(7) 0.128(7) 0.013(6) 0.047(6) 0.004(6) C25 0.135(7) 0.138(8) 0.113(8) 0.027(7) 0.005(6) 0.003(6) C26 0.130(8) 0.140(7) 0.092(5) -0.002(7) 0.019(6) -0.021(5) O6A 0.158(8) 0.132(6) 0.163(6) 0.019(6) 0.012(6) 0.006(5) C23A 0.131(6) 0.136(8) 0.098(7) 0.012(5) 0.002(5) 0.017(6) C24A 0.135(8) 0.123(6) 0.092(5) -0.011(6) 0.016(5) 0.008(4) C25A 0.129(7) 0.127(7) 0.127(8) -0.008(6) 0.037(6) 0.001(6) C26A 0.130(7) 0.124(7) 0.132(7) -0.004(6) 0.031(6) -0.005(6) O1 0.0719(11) 0.0478(9) 0.0611(9) -0.0049(8) -0.0103(8) 0.0047(7) N1 0.109(2) 0.151(3) 0.102(2) -0.003(2) 0.0472(19) 0.011(2) C1 0.0722(18) 0.091(2) 0.0884(19) -0.0006(17) 0.0215(16) 0.0069(16) C2 0.0611(15) 0.0601(14) 0.0710(14) -0.0046(12) 0.0102(11) 0.0067(11) N2 0.0654(13) 0.0544(11) 0.0580(10) -0.0067(10) -0.0046(9) -0.0025(9) O2 0.0608(9) 0.0456(8) 0.0548(8) -0.0073(7) -0.0015(7) 0.0039(6) O3 0.0728(11) 0.0532(9) 0.0913(12) 0.0041(9) 0.0319(9) 0.0106(8) N3 0.0669(12) 0.0477(10) 0.0623(11) -0.0083(9) -0.0018(9) -0.0028(8) C3 0.0589(15) 0.0755(18) 0.0919(19) 0.0032(14) 0.0015(13) 0.0158(15) O4 0.0522(9) 0.0697(11) 0.0885(12) 0.0006(9) 0.0156(8) 0.0259(9) C4 0.0755(19) 0.0727(18) 0.0796(17) -0.0093(15) -0.0090(14) 0.0260(14) O5 0.0568(11) 0.0828(13) 0.1073(14) 0.0057(10) 0.0289(10) 0.0271(11) C5 0.0801(19) 0.0790(18) 0.0609(14) -0.0164(15) 0.0061(12) 0.0105(12) C6 0.0577(14) 0.0605(14) 0.0665(13) -0.0055(12) 0.0068(11) 0.0000(11) C7 0.0564(13) 0.0451(11) 0.0568(12) -0.0043(10) 0.0002(9) 0.0040(9) C8 0.0536(12) 0.0452(11) 0.0498(10) -0.0032(10) 0.0058(9) -0.0001(9) C9 0.0535(12) 0.0501(12) 0.0493(11) -0.0071(10) 0.0033(9) -0.0022(9) C10 0.0483(11) 0.0462(11) 0.0485(10) -0.0032(10) 0.0067(9) -0.0019(8) C11 0.0767(17) 0.0562(14) 0.0639(14) -0.0129(13) -0.0084(12) -0.0073(11) C12 0.0497(11) 0.0428(11) 0.0496(10) -0.0055(9) 0.0032(9) 0.0044(8) C13 0.0596(14) 0.0544(13) 0.0609(12) -0.0001(11) 0.0146(10) 0.0022(10) C14 0.0499(13) 0.0651(15) 0.0802(16) -0.0023(12) 0.0120(12) 0.0117(13) C15 0.0534(14) 0.0703(16) 0.0662(14) -0.0143(12) -0.0029(11) 0.0068(12) C16 0.0624(15) 0.0616(14) 0.0539(12) -0.0090(12) 0.0041(10) -0.0032(10) C17 0.0514(12) 0.0468(11) 0.0519(11) -0.0041(10) 0.0069(9) 0.0045(9) C18 0.0531(12) 0.0535(13) 0.0579(12) -0.0034(11) 0.0116(9) 0.0003(10) C19 0.0587(14) 0.0561(13) 0.0679(13) -0.0014(12) 0.0203(11) 0.0014(11) C20 0.0502(13) 0.0587(14) 0.0635(12) -0.0014(11) 0.0107(10) 0.0045(10) C21 0.100(2) 0.0572(15) 0.096(2) 0.0153(15) 0.0391(17) 0.0134(14) C22 0.0651(17) 0.090(2) 0.122(2) 0.0003(16) 0.0183(17) 0.051(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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C23 O6 C26 . . 106.2(12) ? O6 C23 C24 . . 107.9(11) ? O6 C23 H23 . . 126.0 ? C24 C23 H23 . . 126.0 ? C25 C24 C23 . . 107.6(10) ? C25 C24 H24 . . 126.2 ? C23 C24 H24 . . 126.2 ? C26 C25 C24 . . 108.4(12) ? C26 C25 H25 . . 125.8 ? C24 C25 H25 . . 125.8 ? C25 C26 O6 . . 109.4(12) ? C25 C26 H26 . . 125.3 ? O6 C26 H26 . . 125.3 ? C23A O6A C26A . . 104.6(11) ? C24A C23A O6A . . 110.3(11) ? C24A C23A H23A . . 124.9 ? O6A C23A H23A . . 124.9 ? C25A C24A C23A . . 110.9(12) ? C25A C24A H24A . . 124.5 ? C23A C24A H24A . . 124.5 ? C24A C25A C26A . . 103.7(12) ? C24A C25A H25A . . 128.2 ? C26A C25A H25A . . 128.2 ? O6A C26A C25A . . 110.4(11) ? O6A C26A H26A . . 124.8 ? C25A C26A H26A . . 124.8 ? C8 O1 C7 . . 118.95(17) ? N1 C1 C2 . . 179.1(4) ? C7 C2 C3 . . 118.9(2) ? C7 C2 C1 . . 120.2(2) ? C3 C2 C1 . . 120.9(3) ? C8 N2 C11 . . 114.0(2) ? C10 O2 C12 . . 118.69(16) ? C19 O3 C21 . . 116.5(2) ? C11 N3 C10 . . 114.6(2) ? C4 C3 C2 . . 119.6(3) ? C4 C3 H3 . . 120.2 ? C2 C3 H3 . . 120.2 ? C20 O4 C22 . . 115.0(2) ? C5 C4 C3 . . 120.6(3) ? C5 C4 H4 . . 119.7 ? C3 C4 H4 . . 119.7 ? C4 C5 C6 . . 120.6(3) ? C4 C5 H5 . . 119.7 ? C6 C5 H5 . . 119.7 ? C7 C6 C5 . . 119.1(3) ? C7 C6 H6 . . 120.5 ? C5 C6 H6 . . 120.5 ? C6 C7 C2 . . 121.2(2) ? C6 C7 O1 . . 118.9(2) ? C2 C7 O1 . . 119.7(2) ? N2 C8 O1 . . 119.28(19) ? N2 C8 C9 . . 124.5(2) ? O1 C8 C9 . . 116.25(19) ? C10 C9 C8 . . 115.1(2) ? C10 C9 H9 . . 122.4 ? C8 C9 H9 . . 122.4 ? N3 C10 O2 . . 112.50(18) ? N3 C10 C9 . . 123.5(2) ? O2 C10 C9 . . 123.94(19) ? N3 C11 N2 . . 128.3(2) ? N3 C11 H11 . . 115.9 ? N2 C11 H11 . . 115.9 ? C13 C12 C17 . . 122.7(2) ? C13 C12 O2 . . 117.12(19) ? C17 C12 O2 . . 120.1(2) ? C12 C13 C14 . . 119.1(2) ? C12 C13 H13 . . 120.4 ? C14 C13 H13 . . 120.4 ? C13 C14 C15 . . 120.0(2) ? C13 C14 H14 . . 120.0 ? C15 C14 H14 . . 120.0 ? C16 C15 C14 . . 119.8(2) ? C16 C15 H15 . . 120.1 ? C14 C15 H15 . . 120.1 ? C15 C16 C17 . . 121.8(2) ? C15 C16 H16 . . 119.1 ? C17 C16 H16 . . 119.1 ? C12 C17 C16 . . 116.6(2) ? C12 C17 C18 . . 122.6(2) ? C16 C17 C18 . . 120.8(2) ? C19 C18 C20 . . 116.9(2) ? C19 C18 C17 . . 121.9(2) ? C20 C18 C17 . . 121.0(2) ? O3 C19 C18 . . 121.9(2) ? O3 C19 H19 . . 119.0 ? C18 C19 H19 . . 119.0 ? O5 C20 O4 . . 122.4(2) ? O5 C20 C18 . . 125.5(2) ? O4 C20 C18 . . 112.0(2) ? O3 C21 H21A . . 109.5 ? O3 C21 H21B . . 109.5 ? H21A C21 H21B . . 109.5 ? O3 C21 H21C . . 109.5 ? H21A C21 H21C . . 109.5 ? H21B C21 H21C . . 109.5 ? O4 C22 H22A . . 109.5 ? O4 C22 H22B . . 109.5 ? H22A C22 H22B . . 109.5 ? O4 C22 H22C . . 109.5 ? H22A C22 H22C . . 109.5 ? H22B C22 H22C . . 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O6 C23 . 1.363(13) ? O6 C26 . 1.384(14) ? C23 C24 . 1.387(14) ? C23 H23 . 0.93 ? C24 C25 . 1.351(15) ? C24 H24 . 0.93 ? C25 C26 . 1.338(13) ? C25 H25 . 0.93 ? C26 H26 . 0.93 ? O6A C23A . 1.349(14) ? O6A C26A . 1.379(13) ? C23A C24A . 1.342(13) ? C23A H23A . 0.93 ? C24A C25A . 1.341(14) ? C24A H24A . 0.93 ? C25A C26A . 1.409(13) ? C25A H25A . 0.93 ? C26A H26A . 0.93 ? O1 C8 . 1.362(3) ? O1 C7 . 1.393(3) ? N1 C1 . 1.137(4) ? C1 C2 . 1.429(4) ? C2 C7 . 1.379(4) ? C2 C3 . 1.394(4) ? N2 C8 . 1.317(3) ? N2 C11 . 1.331(3) ? O2 C10 . 1.355(3) ? O2 C12 . 1.404(3) ? O3 C19 . 1.330(3) ? O3 C21 . 1.437(3) ? N3 C11 . 1.320(3) ? N3 C10 . 1.329(3) ? C3 C4 . 1.369(4) ? C3 H3 . 0.93 ? O4 C20 . 1.329(3) ? O4 C22 . 1.451(3) ? C4 C5 . 1.366(4) ? C4 H4 . 0.93 ? O5 C20 . 1.204(3) ? C5 C6 . 1.375(4) ? C5 H5 . 0.93 ? C6 C7 . 1.371(3) ? C6 H6 . 0.93 ? C8 C9 . 1.372(3) ? C9 C10 . 1.367(3) ? C9 H9 . 0.93 ? C11 H11 . 0.93 ? C12 C13 . 1.373(3) ? C12 C17 . 1.382(3) ? C13 C14 . 1.373(4) ? C13 H13 . 0.93 ? C14 C15 . 1.379(4) ? C14 H14 . 0.93 ? C15 C16 . 1.371(4) ? C15 H15 . 0.93 ? C16 C17 . 1.390(3) ? C16 H16 . 0.93 ? C17 C18 . 1.485(3) ? C18 C19 . 1.334(3) ? C18 C20 . 1.468(3) ? C19 H19 . 0.93 ? C21 H21A . 0.96 ? C21 H21B . 0.96 ? C21 H21C . 0.96 ? C22 H22A . 0.96 ? C22 H22B . 0.96 ? C22 H22C . 0.96 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C9 H9 O3 . 0.93 2.59 3.215(3) 125.0 ? C21 H21B O2 1_565 0.96 2.55 3.454(3) 157.1 ? C21 H21C O5 2_556 0.96 2.47 3.418(4) 167.8 ? C22 H22A O5 2_546 0.96 2.59 3.521(4) 163.2 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C26 O6 C23 C24 . . . . -6.(2) ? O6 C23 C24 C25 . . . . 7.(3) ? C23 C24 C25 C26 . . . . -5.(3) ? C24 C25 C26 O6 . . . . 2.(3) ? C23 O6 C26 C25 . . . . 3.(2) ? C26A O6A C23A C24A . . . . -2.(2) ? O6A C23A C24A C25A . . . . 3.(2) ? C23A C24A C25A C26A . . . . -2.6(19) ? C23A O6A C26A C25A . . . . 1.(2) ? C24A C25A C26A O6A . . . . 1.2(19) ? C7 C2 C3 C4 . . . . -0.3(4) ? C1 C2 C3 C4 . . . . -178.7(3) ? C2 C3 C4 C5 . . . . -1.2(5) ? C3 C4 C5 C6 . . . . 1.5(5) ? C4 C5 C6 C7 . . . . -0.4(4) ? C5 C6 C7 C2 . . . . -1.0(4) ? C5 C6 C7 O1 . . . . -176.4(2) ? C3 C2 C7 C6 . . . . 1.4(4) ? C1 C2 C7 C6 . . . . 179.8(3) ? C3 C2 C7 O1 . . . . 176.7(2) ? C1 C2 C7 O1 . . . . -4.9(4) ? C8 O1 C7 C6 . . . . -97.2(3) ? C8 O1 C7 C2 . . . . 87.4(3) ? C11 N2 C8 O1 . . . . -178.8(2) ? C11 N2 C8 C9 . . . . 0.7(4) ? C7 O1 C8 N2 . . . . -1.9(3) ? C7 O1 C8 C9 . . . . 178.6(2) ? N2 C8 C9 C10 . . . . -2.1(3) ? O1 C8 C9 C10 . . . . 177.4(2) ? C11 N3 C10 O2 . . . . 178.5(2) ? C11 N3 C10 C9 . . . . -0.8(4) ? C12 O2 C10 N3 . . . . 168.21(19) ? C12 O2 C10 C9 . . . . -12.5(3) ? C8 C9 C10 N3 . . . . 2.2(3) ? C8 C9 C10 O2 . . . . -177.1(2) ? C10 N3 C11 N2 . . . . -0.9(4) ? C8 N2 C11 N3 . . . . 1.0(4) ? C10 O2 C12 C13 . . . . -93.5(2) ? C10 O2 C12 C17 . . . . 90.2(2) ? C17 C12 C13 C14 . . . . 1.1(3) ? O2 C12 C13 C14 . . . . -175.2(2) ? C12 C13 C14 C15 . . . . -0.3(4) ? C13 C14 C15 C16 . . . . -0.3(4) ? C14 C15 C16 C17 . . . . 0.1(4) ? C13 C12 C17 C16 . . . . -1.2(3) ? O2 C12 C17 C16 . . . . 174.95(19) ? C13 C12 C17 C18 . . . . 177.1(2) ? O2 C12 C17 C18 . . . . -6.7(3) ? C15 C16 C17 C12 . . . . 0.6(3) ? C15 C16 C17 C18 . . . . -177.8(2) ? C12 C17 C18 C19 . . . . -102.3(3) ? C16 C17 C18 C19 . . . . 75.9(3) ? C12 C17 C18 C20 . . . . 82.5(3) ? C16 C17 C18 C20 . . . . -99.2(3) ? C21 O3 C19 C18 . . . . 171.8(2) ? C20 C18 C19 O3 . . . . 176.4(2) ? C17 C18 C19 O3 . . . . 1.1(4) ? C22 O4 C20 O5 . . . . -3.5(4) ? C22 O4 C20 C18 . . . . 175.3(2) ? C19 C18 C20 O5 . . . . 9.2(4) ? C17 C18 C20 O5 . . . . -175.4(2) ? C19 C18 C20 O4 . . . . -169.5(2) ? C17 C18 C20 O4 . . . . 5.9(3) ?