#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:42:52 +0300 (Fri, 01 May 2020) $ #$Revision: 251338 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240430.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_7240430 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 'C24 H20.5 N3 O6' _chemical_formula_weight 446.93 _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 98.614(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.4202(6) _cell_length_b 7.8510(4) _cell_length_c 24.3664(12) _cell_measurement_reflns_used 5483 _cell_measurement_temperature 273.(2) _cell_measurement_theta_max 66.8188 _cell_measurement_theta_min 3.6693 _cell_volume 2349.2(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 833)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'XT, VERSION 2014/5' _diffrn_ambient_temperature 273.(2) _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'BRUKER D8 QUEST' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0680 _diffrn_reflns_av_unetI/netI 0.0436 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 18643 _diffrn_reflns_theta_full 66.89 _diffrn_reflns_theta_max 66.89 _diffrn_reflns_theta_min 3.67 _exptl_absorpt_coefficient_mu 0.769 _exptl_absorpt_correction_T_max 0.93 _exptl_absorpt_correction_T_min 0.78 _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 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 934 _exptl_crystal_size_max 0.580 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.954 _refine_diff_density_min -0.205 _refine_ls_extinction_coef 0.0132(14) _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 328 _refine_ls_number_reflns 4180 _refine_ls_number_restraints 82 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0869 _refine_ls_R_factor_gt 0.0723 _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^)+(0.1505P)^2^+0.4371P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2161 _refine_ls_wR_factor_ref 0.2350 _reflns_number_gt 3198 _reflns_number_total 4180 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00204f2.cif _cod_data_source_block SC154_szp_11_5_block _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_original_formula_sum 'C24 H20.50 N3 O6' _cod_database_code 7240430 _shelx_res_file ; TITL SC153_szp_11_5_0m_a.res in P2(1)/n SC154_szp_11_5_block_0m.res created by SHELXL-2016/6 at 09:12:23 on 01-Jun-2018 REM Old TITL SC153_szp_11_5_0m in P2/n REM SHELXT solution in P2(1)/n REM R1 0.198, Rweak 0.012, Alpha 0.050, Orientation as input REM Formula found by SHELXT: C49 N6 O10 CELL 1.54178 12.4202 7.8510 24.3664 90.000 98.614 90.000 ZERR 4 0.0006 0.0004 0.0012 0.000 0.003 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 96 82 12 24 TEMP 0 SIZE 0.10 0.18 0.58 L.S. 10 BOND $H LIST 4 acta htab conf FMAP 2 PLAN 50 SIMU_ETAC 0.01 0.02 O1 > C4 delu_ETAC 0.01 0.02 O1 > C4 RIGU_ETAC O1 > C4 FLAT_ETAC O1 > C4 SADI_ETAC C1 C2 C3 C4 SADI_ETAC 0.02 O1 C2 O2 C2 O1 C3 SADI_ETAC 0.02 C3 C4 C1 C2 DFIX_ETAC 1.53 0.01 C1 C2 C3 C4 SADI_ETAC 0.04 O2 C1 O1 C4 O1 C1 SAME_ETAC O1 > C4 WGHT 0.150500 0.437100 EXTI 0.013224 FVAR 0.20631 RESI 2 ETAC PART -1 10.5 O1 4 0.936014 -0.418868 0.456546 10.50000 0.09681 0.17258 = 0.20505 -0.10865 0.05854 -0.01017 O2 4 1.028031 -0.415289 0.387645 10.50000 0.13300 0.24982 = 0.18319 -0.10763 0.07320 -0.04577 C1 1 0.854900 -0.301963 0.371982 10.50000 0.17136 0.19517 = 0.17002 -0.09769 0.03374 -0.00465 AFIX 33 H1A 2 0.797050 -0.285894 0.393553 10.50000 -1.50000 H1B 2 0.877063 -0.193480 0.359331 10.50000 -1.50000 H1C 2 0.829885 -0.372964 0.340577 10.50000 -1.50000 AFIX 0 C2 1 0.947310 -0.383485 0.406208 10.50000 0.10372 0.16746 = 0.18383 -0.13397 0.04387 -0.02332 C3 1 1.016787 -0.495528 0.486710 10.50000 0.11040 0.18130 = 0.20609 -0.11136 0.04741 -0.01382 AFIX 43 H3 2 1.080828 -0.529259 0.474367 10.50000 -1.20000 AFIX 0 C4 1 0.990933 -0.522025 0.545468 10.50000 0.13792 0.21234 = 0.21599 -0.09074 0.04682 -0.02879 AFIX 33 H4A 2 1.050904 -0.578687 0.567522 10.50000 -1.50000 H4B 2 0.979123 -0.413567 0.561760 10.50000 -1.50000 H4C 2 0.926524 -0.590469 0.544044 10.50000 -1.50000 AFIX 0 PART 0 RESI 0 REM REM DSR REPLACE ETHYLAC WITH O2 C2 O1 ON O1_1Z C1_1Z C4_1Z>>3 PART -1 REM !OCC 10.5 RESI ETAC O1 4 0.609333 0.140933 0.482145 11.00000 0.06898 0.04676 = 0.05774 0.00481 -0.00820 -0.00402 C1 1 0.830077 0.084530 0.478493 11.00000 0.07112 0.09913 = 0.07742 0.00801 0.02094 0.00307 N1 3 0.867429 0.112874 0.439459 11.00000 0.10366 0.15625 = 0.09624 0.00867 0.04356 -0.00632 C2 1 0.784391 0.048010 0.527720 11.00000 0.05955 0.06096 = 0.06559 0.00508 0.01142 -0.00084 O2 4 0.547584 0.117235 0.319248 11.00000 0.06676 0.05148 = 0.09178 0.01151 0.02954 0.00380 N2 3 0.671180 0.411967 0.505608 11.00000 0.06192 0.05462 = 0.05222 -0.00169 -0.00296 -0.00421 O3 4 0.487581 0.610084 0.368693 11.00000 0.05910 0.04449 = 0.05536 0.00462 -0.00099 -0.00725 N3 3 0.607111 0.644052 0.446071 11.00000 0.06242 0.04729 = 0.05841 -0.00187 -0.00114 -0.00754 C3 1 0.848036 -0.019380 0.574353 11.00000 0.05669 0.07642 = 0.08338 0.01024 -0.00127 0.00754 AFIX 43 H3 2 0.921503 -0.041403 0.574005 11.00000 -1.20000 AFIX 0 C4 1 0.802051 -0.053284 0.620899 11.00000 0.07659 0.07347 = 0.06979 0.01787 -0.00829 -0.00089 AFIX 43 H4 2 0.844727 -0.097652 0.652260 11.00000 -1.20000 AFIX 0 O4 4 0.691791 0.514751 0.246940 11.00000 0.05690 0.07799 = 0.11891 0.03086 0.03500 0.00802 C5 1 0.694224 -0.022497 0.621608 11.00000 0.07772 0.07127 = 0.05848 0.01082 0.00553 -0.01001 AFIX 43 H5 2 0.663598 -0.047959 0.653199 11.00000 -1.20000 AFIX 0 O5 4 0.531047 0.645495 0.232939 11.00000 0.05069 0.06832 = 0.08317 0.02441 0.01487 0.00029 C6 1 0.630178 0.046249 0.575723 11.00000 0.05670 0.05808 = 0.06315 0.00283 0.00844 -0.00379 AFIX 43 H6 2 0.556796 0.068069 0.576415 11.00000 -1.20000 AFIX 0 C7 1 0.675575 0.081894 0.529329 11.00000 0.05661 0.04550 = 0.05153 0.00035 -0.00297 -0.00088 C8 1 0.608332 0.310670 0.471519 11.00000 0.04844 0.04527 = 0.04921 0.00077 0.00778 -0.00145 C9 1 0.540833 0.363638 0.424929 11.00000 0.05181 0.04667 = 0.04627 -0.00137 -0.00007 -0.00527 AFIX 43 H9 2 0.495491 0.289273 0.402482 11.00000 -1.20000 AFIX 0 C00T 1 0.618104 -0.020797 0.339599 11.00000 0.09165 0.05648 = 0.09314 0.01717 0.03514 0.01470 AFIX 137 H00A 2 0.581742 -0.127087 0.330224 11.00000 -1.50000 H00B 2 0.636353 -0.012029 0.379198 11.00000 -1.50000 H00C 2 0.683416 -0.015659 0.322997 11.00000 -1.50000 AFIX 0 C10 1 0.545256 0.535139 0.413898 11.00000 0.04598 0.04739 = 0.04665 -0.00008 0.00722 -0.00188 C11 1 0.665673 0.576045 0.490557 11.00000 0.07296 0.05226 = 0.06279 -0.00602 -0.00739 -0.01266 AFIX 43 H11 2 0.708015 0.651230 0.514149 11.00000 -1.20000 AFIX 0 C12 1 0.404995 0.517793 0.336832 11.00000 0.04678 0.04684 = 0.04567 0.00535 0.00276 -0.00182 C13 1 0.301006 0.537125 0.349113 11.00000 0.05582 0.05536 = 0.05925 0.00441 0.01492 0.00532 AFIX 43 H13 2 0.288241 0.602965 0.379209 11.00000 -1.20000 AFIX 0 C14 1 0.215445 0.456489 0.315732 11.00000 0.04831 0.06520 = 0.07613 0.01064 0.01105 0.00017 AFIX 43 H14 2 0.144694 0.467973 0.323432 11.00000 -1.20000 AFIX 0 C15 1 0.235537 0.359579 0.271247 11.00000 0.05227 0.06706 = 0.06643 0.00923 -0.00410 -0.01199 AFIX 43 H15 2 0.178186 0.307024 0.248577 11.00000 -1.20000 AFIX 0 C16 1 0.340404 0.340456 0.260318 11.00000 0.05952 0.05994 = 0.05434 -0.00290 0.00710 -0.00854 AFIX 43 H16 2 0.353014 0.273395 0.230467 11.00000 -1.20000 AFIX 0 C17 1 0.427646 0.418768 0.292745 11.00000 0.04810 0.04921 = 0.04942 0.00456 0.00744 -0.00196 C18 1 0.540930 0.392102 0.281942 11.00000 0.04910 0.05160 = 0.05713 0.00083 0.01168 -0.00066 C19 1 0.593508 0.245708 0.295068 11.00000 0.05660 0.05703 = 0.06957 0.00394 0.02120 -0.00067 AFIX 43 H19 2 0.664024 0.232788 0.287168 11.00000 -1.20000 AFIX 0 C20 1 0.597644 0.518219 0.253104 11.00000 0.04870 0.05558 = 0.06494 0.00396 0.01229 0.00023 C21 1 0.578083 0.771008 0.200440 11.00000 0.06629 0.08435 = 0.11409 0.04594 0.02006 -0.00208 AFIX 137 H21A 2 0.526390 0.860645 0.190217 11.00000 -1.50000 H21B 2 0.596689 0.718507 0.167536 11.00000 -1.50000 H21C 2 0.642496 0.817461 0.221923 11.00000 -1.50000 AFIX 0 HKLF 4 REM SC153_szp_11_5_0m_a.res in P2(1)/n REM R1 = 0.0723 for 3198 Fo > 4sig(Fo) and 0.0869 for all 4180 data REM 328 parameters refined using 82 restraints END WGHT 0.1505 0.4371 REM Instructions for potential hydrogen bonds HTAB C9 O2 EQIV $1 x, y-1, z HTAB C00T O3_$1 EQIV $2 -x+3/2, y-1/2, -z+1/2 HTAB C00T O4_$2 EQIV $3 -x+3/2, y+3/2, -z+1/2 HTAB_2 C21_0 O2_$3 EQIV $4 -x+3/2, y+1/2, -z+1/2 HTAB C21 O4_$4 REM Highest difference peak 0.954, deepest hole -0.205, 1-sigma level 0.076 Q1 1 0.9342 -0.2972 0.3672 11.00000 0.05 0.95 Q2 1 0.9103 -0.3586 0.4065 11.00000 0.05 0.75 Q3 1 0.8414 -0.3774 0.3761 11.00000 0.05 0.69 Q4 1 0.9766 -0.5141 0.5716 11.00000 0.05 0.26 Q5 1 0.6828 0.0633 0.3674 11.00000 0.05 0.17 Q6 1 0.6805 0.0513 0.6019 11.00000 0.05 0.17 Q7 1 0.6452 0.0036 0.5830 11.00000 0.05 0.17 Q8 1 0.9606 0.0319 0.4832 11.00000 0.05 0.16 Q9 1 0.5173 0.7963 0.1637 11.00000 0.05 0.16 Q10 1 0.6731 0.5456 0.4657 11.00000 0.05 0.15 Q11 1 0.7447 0.6035 0.5198 11.00000 0.05 0.15 Q12 1 0.6260 0.6228 0.4575 11.00000 0.05 0.15 Q13 1 0.7558 0.6217 0.5032 11.00000 0.05 0.15 Q14 1 0.6401 0.4965 0.2141 11.00000 0.05 0.15 Q15 1 0.5841 -0.0079 0.6328 11.00000 0.05 0.15 Q16 1 0.6128 0.6018 0.4242 11.00000 0.05 0.14 Q17 1 0.6558 0.5413 0.2725 11.00000 0.05 0.14 Q18 1 0.6593 0.4493 0.4974 11.00000 0.05 0.14 Q19 1 0.5906 -0.0791 0.3705 11.00000 0.05 0.13 Q20 1 0.6507 -0.0395 0.2924 11.00000 0.05 0.13 Q21 1 0.4683 0.4595 0.3810 11.00000 0.05 0.13 Q22 1 0.5357 0.4421 0.1903 11.00000 0.05 0.13 Q23 1 0.5460 0.3736 0.4633 11.00000 0.05 0.13 Q24 1 0.2370 0.4410 0.2832 11.00000 0.05 0.12 Q25 1 0.4641 0.1060 0.3212 11.00000 0.05 0.12 Q26 1 0.5222 0.4810 0.4280 11.00000 0.05 0.12 Q27 1 0.8235 -0.0427 0.5445 11.00000 0.05 0.12 Q28 1 0.8803 0.1226 0.4515 11.00000 0.05 0.12 Q29 1 0.3034 0.5223 0.2963 11.00000 0.05 0.11 Q30 1 0.4585 0.0487 0.3241 11.00000 0.05 0.11 Q31 1 0.6831 0.0939 0.5634 11.00000 0.05 0.11 Q32 1 0.8137 -0.0929 0.5923 11.00000 0.05 0.11 Q33 1 0.6034 0.4838 0.4541 11.00000 0.05 0.11 Q34 1 0.3127 0.4495 0.2619 11.00000 0.05 0.11 Q35 1 0.4828 0.0073 0.3323 11.00000 0.05 0.11 Q36 1 0.5144 0.0018 0.3416 11.00000 0.05 0.10 Q37 1 0.5062 0.0109 0.2894 11.00000 0.05 0.10 Q38 1 0.8048 0.1613 0.4365 11.00000 0.05 0.10 Q39 1 0.7741 0.0363 0.5998 11.00000 0.05 0.10 Q40 1 0.5369 0.0993 0.3018 11.00000 0.05 0.10 Q41 1 0.5359 -0.0143 0.5921 11.00000 0.05 0.10 Q42 1 0.6579 0.6643 0.5312 11.00000 0.05 0.10 Q43 1 0.4830 0.4555 0.4548 11.00000 0.05 0.10 Q44 1 0.8433 0.0396 0.4900 11.00000 0.05 0.09 Q45 1 0.9243 0.1540 0.4699 11.00000 0.05 0.09 Q46 1 0.6417 0.0787 0.3003 11.00000 0.05 0.09 Q47 1 0.6020 0.0476 0.3240 11.00000 0.05 0.09 Q48 1 0.1818 0.2354 0.2402 11.00000 0.05 0.09 Q49 1 1.1775 -0.4989 0.4784 11.00000 0.05 0.09 Q50 1 0.5260 0.0177 0.5449 11.00000 0.05 0.09 ; _shelx_res_checksum 93262 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 O1_2 0.9360(7) -0.4189(12) 0.4565(4) 0.154(3) Uani d U P D 0.5 A -1 O O2_2 1.0280(8) -0.4153(17) 0.3876(5) 0.184(4) Uani d U P D 0.5 A -1 C C1_2 0.8549(13) -0.302(2) 0.3720(6) 0.178(5) Uani d U P D 0.5 A -1 H H1A_2 0.79705 -0.285894 0.393553 0.267 Uiso calc U P R 0.5 A -1 H H1B_2 0.877063 -0.19348 0.359331 0.267 Uiso calc U P R 0.5 A -1 H H1C_2 0.829885 -0.372964 0.340577 0.267 Uiso calc U P R 0.5 A -1 C C2_2 0.9473(9) -0.3835(16) 0.4062(5) 0.149(4) Uani d U P D 0.5 A -1 C C3_2 1.0168(14) -0.496(3) 0.4867(6) 0.164(5) Uani d U P D 0.5 A -1 H H3_2 1.080828 -0.529259 0.474367 0.196 Uiso calc U P R 0.5 A -1 C C4_2 0.991(2) -0.522(3) 0.5455(6) 0.187(6) Uani d U P D 0.5 A -1 H H4A_2 1.050904 -0.578687 0.567522 0.28 Uiso calc U P R 0.5 A -1 H H4B_2 0.979123 -0.413567 0.56176 0.28 Uiso calc U P R 0.5 A -1 H H4C_2 0.926524 -0.590469 0.544044 0.28 Uiso calc U P R 0.5 A -1 O O1 0.60933(17) 0.1409(2) 0.48214(8) 0.0596(6) Uani d . . . 1 . . C C1 0.8301(3) 0.0845(6) 0.47849(17) 0.0816(10) Uani d . . . 1 . . N N1 0.8674(4) 0.1129(7) 0.43946(18) 0.1158(14) Uani d . . . 1 . . C C2 0.7844(3) 0.0480(4) 0.52772(14) 0.0618(8) Uani d . . . 1 . . O O2 0.54758(18) 0.1172(3) 0.31925(11) 0.0682(6) Uani d . . . 1 . . N N2 0.6712(2) 0.4120(3) 0.50561(10) 0.0574(6) Uani d . . . 1 . . O O3 0.48758(16) 0.6101(2) 0.36869(8) 0.0540(5) Uani d . . . 1 . . N N3 0.6071(2) 0.6441(3) 0.44607(11) 0.0571(6) Uani d . . . 1 . . C C3 0.8480(3) -0.0194(5) 0.57435(16) 0.0734(9) Uani d . . . 1 . . H H3 0.921503 -0.041403 0.574005 0.088 Uiso calc U . R 1 . . C C4 0.8021(3) -0.0533(5) 0.62090(16) 0.0752(10) Uani d . . . 1 . . H H4 0.844727 -0.097652 0.65226 0.09 Uiso calc U . R 1 . . O O4 0.69179(18) 0.5148(3) 0.24694(13) 0.0824(8) Uani d . . . 1 . . C C5 0.6942(3) -0.0225(4) 0.62161(14) 0.0696(9) Uani d . . . 1 . . H H5 0.663598 -0.047959 0.653199 0.084 Uiso calc U . R 1 . . O O5 0.53105(16) 0.6455(3) 0.23294(10) 0.0669(6) Uani d . . . 1 . . C C6 0.6302(3) 0.0462(4) 0.57572(13) 0.0594(7) Uani d . . . 1 . . H H6 0.556796 0.068069 0.576415 0.071 Uiso calc U . R 1 . . C C7 0.6756(2) 0.0819(3) 0.52933(12) 0.0523(6) Uani d . . . 1 . . C C8 0.6083(2) 0.3107(3) 0.47152(11) 0.0476(6) Uani d . . . 1 . . C C9 0.5408(2) 0.3636(3) 0.42493(11) 0.0490(6) Uani d . . . 1 . . H H9 0.495491 0.289273 0.402482 0.059 Uiso calc U . R 1 . . C C00T 0.6181(3) -0.0208(4) 0.33960(18) 0.0782(10) Uani d . . . 1 . . H H00A 0.581742 -0.127087 0.330224 0.117 Uiso calc U . R 1 . . H H00B 0.636353 -0.012029 0.379198 0.117 Uiso calc U . R 1 . . H H00C 0.683416 -0.015659 0.322997 0.117 Uiso calc U . R 1 . . C C10 0.5453(2) 0.5351(3) 0.41390(11) 0.0466(6) Uani d . . . 1 . . C C11 0.6657(3) 0.5760(4) 0.49056(13) 0.0645(8) Uani d . . . 1 . . H H11 0.708015 0.65123 0.514149 0.077 Uiso calc U . R 1 . . C C12 0.4050(2) 0.5178(3) 0.33683(11) 0.0469(6) Uani d . . . 1 . . C C13 0.3010(2) 0.5371(4) 0.34911(13) 0.0562(7) Uani d . . . 1 . . H H13 0.288241 0.602965 0.379209 0.067 Uiso calc U . R 1 . . C C14 0.2154(2) 0.4565(4) 0.31573(14) 0.0630(8) Uani d . . . 1 . . H H14 0.144694 0.467973 0.323432 0.076 Uiso calc U . R 1 . . C C15 0.2355(2) 0.3596(4) 0.27125(14) 0.0632(8) Uani d . . . 1 . . H H15 0.178186 0.307024 0.248577 0.076 Uiso calc U . R 1 . . C C16 0.3404(2) 0.3405(4) 0.26032(13) 0.0581(7) Uani d . . . 1 . . H H16 0.353014 0.273395 0.230467 0.07 Uiso calc U . R 1 . . C C17 0.4276(2) 0.4188(3) 0.29274(11) 0.0489(6) Uani d . . . 1 . . C C18 0.5409(2) 0.3921(3) 0.28194(12) 0.0522(7) Uani d . . . 1 . . C C19 0.5935(2) 0.2457(4) 0.29507(13) 0.0599(7) Uani d . . . 1 . . H H19 0.664024 0.232788 0.287168 0.072 Uiso calc U . R 1 . . C C20 0.5976(2) 0.5182(4) 0.25310(13) 0.0560(7) Uani d . . . 1 . . C C21 0.5781(3) 0.7710(5) 0.20044(19) 0.0876(12) Uani d . . . 1 . . H H21A 0.52639 0.860645 0.190217 0.131 Uiso calc U . R 1 . . H H21B 0.596689 0.718507 0.167536 0.131 Uiso calc U . R 1 . . H H21C 0.642496 0.817461 0.221923 0.131 Uiso calc U . R 1 . . 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 O1_2 0.097(4) 0.173(7) 0.205(8) -0.010(4) 0.059(5) -0.109(7) O2_2 0.133(6) 0.250(11) 0.183(8) -0.046(6) 0.073(6) -0.108(8) C1_2 0.171(10) 0.195(12) 0.170(10) -0.005(9) 0.034(8) -0.098(9) C2_2 0.104(5) 0.167(7) 0.184(8) -0.023(5) 0.044(5) -0.134(7) C3_2 0.110(7) 0.181(9) 0.206(11) -0.014(6) 0.047(8) -0.111(10) C4_2 0.138(11) 0.212(14) 0.216(13) -0.029(10) 0.047(12) -0.091(13) O1 0.0690(12) 0.0468(10) 0.0577(12) -0.0040(8) -0.0082(9) 0.0048(8) C1 0.071(2) 0.099(3) 0.077(2) 0.0031(19) 0.0209(18) 0.008(2) N1 0.104(3) 0.156(4) 0.096(3) -0.006(3) 0.044(2) 0.009(3) C2 0.0595(16) 0.0610(16) 0.0656(18) -0.0008(13) 0.0114(14) 0.0051(14) O2 0.0668(12) 0.0515(11) 0.0918(16) 0.0038(9) 0.0295(11) 0.0115(10) N2 0.0619(14) 0.0546(13) 0.0522(13) -0.0042(10) -0.0030(10) -0.0017(10) O3 0.0591(11) 0.0445(9) 0.0554(11) -0.0073(8) -0.0010(8) 0.0046(8) N3 0.0624(13) 0.0473(12) 0.0584(14) -0.0075(10) -0.0011(11) -0.0019(10) C3 0.0567(17) 0.076(2) 0.083(2) 0.0075(15) -0.0013(16) 0.0102(17) C4 0.077(2) 0.073(2) 0.070(2) -0.0009(16) -0.0083(17) 0.0179(17) O4 0.0569(13) 0.0780(15) 0.119(2) 0.0080(11) 0.0350(13) 0.0309(14) C5 0.078(2) 0.0713(19) 0.0585(18) -0.0100(16) 0.0055(15) 0.0108(15) O5 0.0507(10) 0.0683(13) 0.0832(15) 0.0003(9) 0.0149(10) 0.0244(11) C6 0.0567(16) 0.0581(15) 0.0631(17) -0.0038(12) 0.0084(13) 0.0028(13) C7 0.0566(15) 0.0455(13) 0.0515(15) -0.0009(11) -0.0030(11) 0.0004(11) C8 0.0484(13) 0.0453(12) 0.0492(14) -0.0015(10) 0.0078(10) 0.0008(11) C9 0.0518(13) 0.0467(13) 0.0463(14) -0.0053(10) -0.0001(11) -0.0014(10) C00T 0.092(2) 0.0565(17) 0.093(3) 0.0147(16) 0.035(2) 0.0172(17) C10 0.0460(13) 0.0474(13) 0.0467(14) -0.0019(10) 0.0072(10) -0.0001(10) C11 0.0730(19) 0.0523(15) 0.0628(18) -0.0127(13) -0.0074(14) -0.0060(13) C12 0.0468(13) 0.0468(12) 0.0457(13) -0.0018(10) 0.0028(10) 0.0054(10) C13 0.0558(15) 0.0554(15) 0.0593(16) 0.0053(12) 0.0149(12) 0.0044(12) C14 0.0483(15) 0.0652(17) 0.076(2) 0.0002(12) 0.0111(13) 0.0106(15) C15 0.0523(15) 0.0671(18) 0.0664(18) -0.0120(13) -0.0041(13) 0.0092(14) C16 0.0595(16) 0.0599(16) 0.0543(15) -0.0085(13) 0.0071(12) -0.0029(13) C17 0.0481(13) 0.0492(13) 0.0494(14) -0.0020(10) 0.0074(11) 0.0046(11) C18 0.0491(14) 0.0516(14) 0.0571(16) -0.0007(11) 0.0117(12) 0.0008(12) C19 0.0566(15) 0.0570(15) 0.0696(18) -0.0007(12) 0.0212(13) 0.0039(13) C20 0.0487(14) 0.0556(15) 0.0649(17) 0.0002(11) 0.0123(12) 0.0040(13) C21 0.0663(19) 0.084(2) 0.114(3) -0.0021(17) 0.020(2) 0.046(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 C2_2 O1_2 C3_2 . . 117.0(12) ? C2_2 C1_2 H1A_2 . . 109.5 ? C2_2 C1_2 H1B_2 . . 109.5 ? H1A_2 C1_2 H1B_2 . . 109.5 ? C2_2 C1_2 H1C_2 . . 109.5 ? H1A_2 C1_2 H1C_2 . . 109.5 ? H1B_2 C1_2 H1C_2 . . 109.5 ? O2_2 C2_2 O1_2 . . 122.5(15) ? O2_2 C2_2 C1_2 . . 120.7(14) ? O1_2 C2_2 C1_2 . . 116.8(10) ? O1_2 C3_2 C4_2 . . 109.9(10) ? O1_2 C3_2 H3_2 . . 125.1 ? C4_2 C3_2 H3_2 . . 125.1 ? C3_2 C4_2 H4A_2 . . 109.5 ? C3_2 C4_2 H4B_2 . . 109.5 ? H4A_2 C4_2 H4B_2 . . 109.5 ? C3_2 C4_2 H4C_2 . . 109.5 ? H4A_2 C4_2 H4C_2 . . 109.5 ? H4B_2 C4_2 H4C_2 . . 109.5 ? C8 O1 C7 . . 118.2(2) ? N1 C1 C2 . . 179.3(5) ? C7 C2 C3 . . 119.3(3) ? C7 C2 C1 . . 119.8(3) ? C3 C2 C1 . . 120.9(3) ? C19 O2 C00T . . 116.3(3) ? C8 N2 C11 . . 114.0(2) ? C10 O3 C12 . . 118.85(19) ? C11 N3 C10 . . 115.0(2) ? C4 C3 C2 . . 119.7(3) ? C4 C3 H3 . . 120.2 ? C2 C3 H3 . . 120.2 ? C5 C4 C3 . . 120.5(3) ? C5 C4 H4 . . 119.7 ? C3 C4 H4 . . 119.7 ? C4 C5 C6 . . 120.4(3) ? C4 C5 H5 . . 119.8 ? C6 C5 H5 . . 119.8 ? C20 O5 C21 . . 115.6(2) ? C7 C6 C5 . . 119.4(3) ? C7 C6 H6 . . 120.3 ? C5 C6 H6 . . 120.3 ? C6 C7 C2 . . 120.7(3) ? C6 C7 O1 . . 119.1(3) ? C2 C7 O1 . . 120.0(3) ? N2 C8 O1 . . 119.0(2) ? N2 C8 C9 . . 124.7(2) ? O1 C8 C9 . . 116.3(2) ? C8 C9 C10 . . 114.9(2) ? C8 C9 H9 . . 122.5 ? C10 C9 H9 . . 122.5 ? O2 C00T H00A . . 109.5 ? O2 C00T H00B . . 109.5 ? H00A C00T H00B . . 109.5 ? O2 C00T H00C . . 109.5 ? H00A C00T H00C . . 109.5 ? H00B C00T H00C . . 109.5 ? N3 C10 O3 . . 112.9(2) ? N3 C10 C9 . . 123.5(2) ? O3 C10 C9 . . 123.5(2) ? N3 C11 N2 . . 127.7(3) ? N3 C11 H11 . . 116.1 ? N2 C11 H11 . . 116.1 ? C13 C12 C17 . . 122.4(2) ? C13 C12 O3 . . 117.2(2) ? C17 C12 O3 . . 120.3(2) ? C12 C13 C14 . . 118.8(3) ? C12 C13 H13 . . 120.6 ? C14 C13 H13 . . 120.6 ? C15 C14 C13 . . 120.0(3) ? C15 C14 H14 . . 120.0 ? C13 C14 H14 . . 120.0 ? C16 C15 C14 . . 120.1(3) ? C16 C15 H15 . . 120.0 ? C14 C15 H15 . . 120.0 ? C15 C16 C17 . . 121.5(3) ? C15 C16 H16 . . 119.2 ? C17 C16 H16 . . 119.2 ? C16 C17 C12 . . 117.2(2) ? C16 C17 C18 . . 121.2(3) ? C12 C17 C18 . . 121.6(2) ? C19 C18 C20 . . 116.5(3) ? C19 C18 C17 . . 121.4(3) ? C20 C18 C17 . . 122.0(2) ? C18 C19 O2 . . 121.9(3) ? C18 C19 H19 . . 119.1 ? O2 C19 H19 . . 119.1 ? O4 C20 O5 . . 121.9(3) ? O4 C20 C18 . . 126.5(3) ? O5 C20 C18 . . 111.5(2) ? O5 C21 H21A . . 109.5 ? O5 C21 H21B . . 109.5 ? H21A C21 H21B . . 109.5 ? O5 C21 H21C . . 109.5 ? H21A C21 H21C . . 109.5 ? H21B C21 H21C . . 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 O1_2 C2_2 . 1.286(13) ? O1_2 C3_2 . 1.299(15) ? O2_2 C2_2 . 1.187(11) ? C1_2 C2_2 . 1.461(9) ? C1_2 H1A_2 . 0.96 ? C1_2 H1B_2 . 0.96 ? C1_2 H1C_2 . 0.96 ? C3_2 C4_2 . 1.528(9) ? C3_2 H3_2 . 0.93 ? C4_2 H4A_2 . 0.96 ? C4_2 H4B_2 . 0.96 ? C4_2 H4C_2 . 0.96 ? O1 C8 . 1.357(3) ? O1 C7 . 1.389(3) ? C1 N1 . 1.141(5) ? C1 C2 . 1.431(5) ? C2 C7 . 1.384(4) ? C2 C3 . 1.388(5) ? O2 C19 . 1.338(4) ? O2 C00T . 1.434(4) ? N2 C8 . 1.318(3) ? N2 C11 . 1.338(4) ? O3 C10 . 1.355(3) ? O3 C12 . 1.393(3) ? N3 C11 . 1.324(4) ? N3 C10 . 1.325(3) ? C3 C4 . 1.370(6) ? C3 H3 . 0.93 ? C4 C5 . 1.364(5) ? C4 H4 . 0.93 ? O4 C20 . 1.201(3) ? C5 C6 . 1.381(5) ? C5 H5 . 0.93 ? O5 C20 . 1.343(4) ? O5 C21 . 1.442(4) ? C6 C7 . 1.366(4) ? C6 H6 . 0.93 ? C8 C9 . 1.371(4) ? C9 C10 . 1.376(4) ? C9 H9 . 0.93 ? C00T H00A . 0.96 ? C00T H00B . 0.96 ? C00T H00C . 0.96 ? C11 H11 . 0.93 ? C12 C13 . 1.377(4) ? C12 C17 . 1.389(4) ? C13 C14 . 1.390(4) ? C13 H13 . 0.93 ? C14 C15 . 1.377(5) ? C14 H14 . 0.93 ? C15 C16 . 1.376(4) ? C15 H15 . 0.93 ? C16 C17 . 1.386(4) ? C16 H16 . 0.93 ? C17 C18 . 1.484(4) ? C18 C19 . 1.337(4) ? C18 C20 . 1.456(4) ? C19 H19 . 0.93 ? C21 H21A . 0.96 ? C21 H21B . 0.96 ? C21 H21C . 0.96 ? 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 C3_2 O1_2 C2_2 O2_2 . . . . -1.5(15) ? C3_2 O1_2 C2_2 C1_2 . . . . 178.2(10) ? C2_2 O1_2 C3_2 C4_2 . . . . 178.1(9) ? C7 C2 C3 C4 . . . . 0.8(5) ? C1 C2 C3 C4 . . . . -179.9(4) ? C2 C3 C4 C5 . . . . 0.5(6) ? C3 C4 C5 C6 . . . . -1.2(6) ? C4 C5 C6 C7 . . . . 0.6(5) ? C5 C6 C7 C2 . . . . 0.7(4) ? C5 C6 C7 O1 . . . . 176.0(3) ? C3 C2 C7 C6 . . . . -1.4(5) ? C1 C2 C7 C6 . . . . 179.3(3) ? C3 C2 C7 O1 . . . . -176.6(3) ? C1 C2 C7 O1 . . . . 4.1(5) ? C8 O1 C7 C6 . . . . 100.2(3) ? C8 O1 C7 C2 . . . . -84.6(3) ? C11 N2 C8 O1 . . . . 178.6(3) ? C11 N2 C8 C9 . . . . -1.1(4) ? C7 O1 C8 N2 . . . . 1.1(4) ? C7 O1 C8 C9 . . . . -179.2(2) ? N2 C8 C9 C10 . . . . 2.4(4) ? O1 C8 C9 C10 . . . . -177.2(2) ? C11 N3 C10 O3 . . . . -179.5(3) ? C11 N3 C10 C9 . . . . -0.1(4) ? C12 O3 C10 N3 . . . . -168.5(2) ? C12 O3 C10 C9 . . . . 12.1(4) ? C8 C9 C10 N3 . . . . -1.8(4) ? C8 C9 C10 O3 . . . . 177.5(2) ? C10 N3 C11 N2 . . . . 1.7(5) ? C8 N2 C11 N3 . . . . -1.2(5) ? C10 O3 C12 C13 . . . . 93.6(3) ? C10 O3 C12 C17 . . . . -89.9(3) ? C17 C12 C13 C14 . . . . -0.9(4) ? O3 C12 C13 C14 . . . . 175.5(2) ? C12 C13 C14 C15 . . . . -0.1(4) ? C13 C14 C15 C16 . . . . 1.0(5) ? C14 C15 C16 C17 . . . . -0.9(5) ? C15 C16 C17 C12 . . . . -0.1(4) ? C15 C16 C17 C18 . . . . 177.6(3) ? C13 C12 C17 C16 . . . . 1.0(4) ? O3 C12 C17 C16 . . . . -175.3(2) ? C13 C12 C17 C18 . . . . -176.7(3) ? O3 C12 C17 C18 . . . . 7.0(4) ? C16 C17 C18 C19 . . . . -73.9(4) ? C12 C17 C18 C19 . . . . 103.7(3) ? C16 C17 C18 C20 . . . . 101.6(3) ? C12 C17 C18 C20 . . . . -80.8(4) ? C20 C18 C19 O2 . . . . -176.8(3) ? C17 C18 C19 O2 . . . . -1.0(5) ? C00T O2 C19 C18 . . . . -169.9(3) ? C21 O5 C20 O4 . . . . 3.9(5) ? C21 O5 C20 C18 . . . . -176.0(3) ? C19 C18 C20 O4 . . . . -11.4(5) ? C17 C18 C20 O4 . . . . 172.8(3) ? C19 C18 C20 O5 . . . . 168.5(3) ? C17 C18 C20 O5 . . . . -7.2(4) ?