#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:42:52 +0300 (Fri, 01 May 2020) $ #$Revision: 251338 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240434.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_7240434 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 'C25 H22 N3 O7' _chemical_formula_weight 476.45 _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 96.499(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.5159(6) _cell_length_b 7.7861(5) _cell_length_c 24.3482(10) _cell_measurement_reflns_used 1798 _cell_measurement_temperature 273.(2) _cell_measurement_theta_max 65.4304 _cell_measurement_theta_min 3.5542 _cell_volume 2357.5(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 'SHELXT 2014/5 (Sheldrick, 2014)' _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 0.0720 _diffrn_reflns_av_unetI/netI 0.0541 _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 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 17722 _diffrn_reflns_theta_full 66.92 _diffrn_reflns_theta_max 66.92 _diffrn_reflns_theta_min 3.65 _exptl_absorpt_coefficient_mu 0.833 _exptl_absorpt_correction_T_max 0.78 _exptl_absorpt_correction_T_min 0.62 _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 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 996 _exptl_crystal_size_max 0.510 _exptl_crystal_size_mid 0.360 _exptl_crystal_size_min 0.320 _refine_diff_density_max 0.889 _refine_diff_density_min -0.411 _refine_ls_extinction_coef 0.0037(5) _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 364 _refine_ls_number_reflns 4188 _refine_ls_number_restraints 93 _refine_ls_restrained_S_all 1.134 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0681 _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^)+(0.1014P)^2^+0.8201P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1830 _refine_ls_wR_factor_ref 0.2066 _reflns_number_gt 2962 _reflns_number_total 4188 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00204f2.cif _cod_data_source_block SC155_szp_5_23 _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 7240434 _shelx_res_file ; TITL SC155_szp_5_23_0m_a.res in P2(1)/n SC155_szp_5_23_0m_a.res created by SHELXL-2016/6 at 08:08:16 on 01-Jun-2018 REM Old TITL SC155_szp_5_23_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.194, Rweak 0.014, Alpha 0.044, Orientation as input REM Formula found by SHELXT: C28 N3 O5 CELL 1.54178 12.5159 7.7861 24.3482 90.000 96.499 90.000 ZERR 4.000 0.0006 0.0005 0.0010 0.000 0.004 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 100 88 12 28 TEMP 0 SIZE 0.32 0.36 0.51 L.S. 10 BOND $H LIST 4 acta htab conf HTAB C10 O3 EQIV $1 -x+1/2, y-1/2, -z+3/2 HTAB C20 O4_$1 EQIV $2 x, y+1, z HTAB C22 O2_$2 EQIV $3 -x+1/2, y+1/2, -z+3/2 HTAB C22 O4_$3 HTAB C4_2 N3 FMAP 2 PLAN 200 WGHT 0.101400 0.820100 EXTI 0.003684 FVAR 0.60247 O1 4 0.392068 0.350528 0.519142 11.00000 0.07046 0.04532 = 0.06207 0.00552 -0.00788 -0.00475 N1 3 0.397554 -0.156125 0.557070 11.00000 0.06207 0.04470 = 0.06373 -0.00229 0.00045 -0.00598 C1 1 0.197090 0.546650 0.385949 11.00000 0.09218 0.07114 = 0.07403 0.01913 -0.01673 -0.00033 AFIX 43 H1 2 0.154164 0.591327 0.355628 11.00000 -1.20000 AFIX 0 C2 1 0.304921 0.523545 0.383277 11.00000 0.09240 0.06868 = 0.06642 0.01414 0.00382 -0.00924 AFIX 43 H2 2 0.334492 0.554085 0.351302 11.00000 -1.20000 AFIX 0 N2 3 0.330048 0.075858 0.499059 11.00000 0.05937 0.05193 = 0.06027 -0.00250 -0.00321 -0.00163 O2 4 0.519325 -0.119894 0.630191 11.00000 0.05941 0.04565 = 0.06086 0.00477 -0.00244 -0.00392 O3 4 0.452667 0.370910 0.680353 11.00000 0.07459 0.05173 = 0.09054 0.01007 0.02734 0.00103 N3 3 0.136690 0.351896 0.566437 11.00000 0.11518 0.14383 = 0.09726 -0.00649 0.04099 -0.02278 C3 1 0.369701 0.456055 0.427091 11.00000 0.06743 0.05352 = 0.06563 0.00119 0.01183 -0.00536 AFIX 43 H3 2 0.442925 0.441321 0.425181 11.00000 -1.20000 AFIX 0 C4 1 0.324729 0.410476 0.473913 11.00000 0.05842 0.04058 = 0.05842 0.00119 0.00040 -0.00006 O4 4 0.310568 -0.035365 0.752140 11.00000 0.06081 0.07637 = 0.11283 0.02517 0.02817 0.00533 C5 1 0.216651 0.435520 0.477987 11.00000 0.05951 0.05443 = 0.07059 0.00078 0.00778 -0.00004 O5 4 0.470229 -0.163785 0.764967 11.00000 0.05718 0.06631 = 0.08490 0.02383 0.01430 0.00208 C6 1 0.152132 0.504826 0.432582 11.00000 0.06310 0.06654 = 0.09760 0.00464 -0.00498 0.00582 AFIX 43 H6 2 0.079057 0.522174 0.434265 11.00000 -1.20000 AFIX 0 C7 1 0.171795 0.390398 0.527263 11.00000 0.07103 0.08662 = 0.08229 -0.00373 0.01783 -0.00487 C8 1 0.337212 -0.089468 0.514625 11.00000 0.06575 0.04801 = 0.07036 -0.00468 -0.00489 -0.00604 AFIX 43 H8 2 0.294304 -0.166265 0.492749 11.00000 -1.20000 AFIX 0 C9 1 0.393582 0.179160 0.530624 11.00000 0.05273 0.04440 = 0.05461 -0.00045 0.00960 -0.00135 C10 1 0.463381 0.126759 0.575073 11.00000 0.05266 0.04549 = 0.05448 0.00046 0.00098 -0.00433 AFIX 43 H10 2 0.509295 0.202474 0.595711 11.00000 -1.20000 AFIX 0 C11 1 0.460433 -0.045305 0.586801 11.00000 0.04974 0.04635 = 0.05496 -0.00021 0.00735 -0.00119 C12 1 0.599140 -0.024678 0.661252 11.00000 0.05031 0.04519 = 0.05804 0.00742 0.00270 -0.00257 C13 1 0.703352 -0.040423 0.648275 11.00000 0.05682 0.05681 = 0.06644 0.00672 0.01004 0.00283 AFIX 43 H13 2 0.717908 -0.105928 0.618060 11.00000 -1.20000 AFIX 0 C14 1 0.784602 0.040787 0.680101 11.00000 0.05058 0.07149 = 0.08507 0.01312 0.01087 -0.00151 AFIX 43 H14 2 0.854802 0.031860 0.671328 11.00000 -1.20000 AFIX 0 C15 1 0.762987 0.136582 0.725473 11.00000 0.05941 0.07585 = 0.07550 0.01007 -0.00922 -0.01568 AFIX 43 H15 2 0.818459 0.190605 0.747616 11.00000 -1.20000 AFIX 0 C16 1 0.658121 0.150986 0.737466 11.00000 0.06641 0.06309 = 0.06351 -0.00025 0.00163 -0.00909 AFIX 43 H16 2 0.643814 0.216153 0.767798 11.00000 -1.20000 AFIX 0 C17 1 0.574143 0.071729 0.705847 11.00000 0.05473 0.04563 = 0.05739 0.00508 0.00634 -0.00271 C18 1 0.460985 0.094123 0.717030 11.00000 0.05529 0.05117 = 0.06156 0.00279 0.01246 -0.00401 C19 1 0.404677 -0.037405 0.745423 11.00000 0.05586 0.05690 = 0.06682 0.00448 0.01098 0.00061 C20 1 0.423409 -0.294104 0.796816 11.00000 0.07864 0.07919 = 0.10527 0.03771 0.01841 -0.00088 AFIX 137 H20A 2 0.358474 -0.336004 0.776451 11.00000 -1.50000 H20B 2 0.407212 -0.245949 0.831215 11.00000 -1.50000 H20C 2 0.473356 -0.387162 0.803997 11.00000 -1.50000 AFIX 0 C21 1 0.407050 0.239552 0.703719 11.00000 0.06229 0.05565 = 0.06921 0.00152 0.01909 -0.00084 AFIX 43 H21 2 0.335923 0.248938 0.710994 11.00000 -1.20000 AFIX 0 C22 1 0.382781 0.507115 0.659972 11.00000 0.09509 0.05635 = 0.09104 0.00862 0.02547 0.01106 AFIX 137 H22A 2 0.361818 0.490965 0.621159 11.00000 -1.50000 H22B 2 0.419558 0.614902 0.665811 11.00000 -1.50000 H22C 2 0.319970 0.507075 0.679240 11.00000 -1.50000 AFIX 0 RESI 1 PART -1 PART 0 RESI 0 RESI 2 PART -1 10.5 dfix_2 1.33 0.01 C1 O1 C2 O1 C5 O3 C6 O3 dfix_2 1.21 0.01 C1 O2 C5 O4 dfix_2 1.53 0.01 C1 C3 C4 C5 C3 C4 SADI_2 C1 C4 C3 C5 simu_2 0.01 0.02 C1 > O4 delu_2 0.01 0.02 C1 > O4 SADI_2 0.04 C3 O1 C3 O2 sadi_2 O1 O2 O3 O4 flat_2 C1 O1 O2 C2 C3 C1 1 -0.033116 0.098247 0.429062 10.50000 0.10714 0.11919 = 0.13341 0.01316 -0.02600 0.00298 O2 4 0.027612 0.083215 0.394303 10.50000 0.12275 0.17871 = 0.15465 -0.02879 -0.00904 0.04393 C3 1 0.039139 0.007240 0.473015 10.50000 0.12018 0.11909 = 0.14976 -0.01132 -0.00780 0.00124 AFIX 23 H3A 2 0.054343 -0.106323 0.459476 10.50000 -1.20000 H3AB 2 0.106784 0.069029 0.478716 10.50000 -1.20000 AFIX 0 C2 1 -0.163130 0.218145 0.363528 10.50000 0.15660 0.17376 = 0.14732 0.00406 -0.01348 0.09230 AFIX 33 H2A 2 -0.236270 0.256240 0.362548 10.50000 -1.20000 H2B 2 -0.118659 0.312470 0.354763 10.50000 -1.20000 H2C 2 -0.158992 0.127919 0.336980 10.50000 -1.20000 AFIX 0 O1 4 -0.128839 0.159166 0.414256 10.50000 0.12840 0.17585 = 0.13320 0.00075 -0.01078 0.03492 C4 1 -0.001649 -0.011325 0.525669 10.50000 0.13706 0.09271 = 0.12380 0.02272 -0.03533 -0.03724 AFIX 23 H4A 2 -0.075623 -0.050412 0.519502 10.50000 -1.20000 H4AB 2 -0.001523 0.100339 0.543342 10.50000 -1.20000 AFIX 0 C5 1 0.060381 -0.132338 0.563411 10.50000 0.13271 0.07223 = 0.09557 0.01200 0.01753 0.00820 C6 1 0.094010 -0.250219 0.647054 10.50000 0.19857 0.12871 = 0.08217 0.01844 0.00431 0.04966 AFIX 33 H6A 2 0.072642 -0.243242 0.683632 10.50000 -1.20000 H6B 2 0.079734 -0.363603 0.632557 10.50000 -1.20000 H6C 2 0.169498 -0.226202 0.648417 10.50000 -1.20000 AFIX 0 O3 4 0.036949 -0.132223 0.613476 10.50000 0.18457 0.10932 = 0.09834 -0.00239 0.01759 0.05394 O4 4 0.102118 -0.245304 0.540825 10.50000 0.18260 0.11975 = 0.11437 0.01230 0.02476 0.07015 PART 0 RESI 0 HKLF 4 REM SC155_szp_5_23_0m_a.res in P2(1)/n REM R1 = 0.0681 for 2962 Fo > 4sig(Fo) and 0.0921 for all 4188 data REM 364 parameters refined using 93 restraints END WGHT 0.1014 0.8201 REM Instructions for potential hydrogen bonds HTAB C10 O3 HTAB C20 O4_$1 HTAB C22 O2_$2 HTAB C22 O4_$3 HTAB C4_2 N3 REM Highest difference peak 0.889, deepest hole -0.411, 1-sigma level 0.050 Q1 1 0.0536 -0.0603 0.5124 11.00000 0.05 0.89 Q2 1 0.0203 0.0157 0.4059 11.00000 0.05 0.30 Q3 1 -0.1151 0.0770 0.3998 11.00000 0.05 0.25 Q4 1 -0.0836 0.2398 0.4156 11.00000 0.05 0.24 Q5 1 0.4760 -0.3107 0.8315 11.00000 0.05 0.16 Q6 1 -0.0755 -0.0427 0.3953 11.00000 0.05 0.16 Q7 1 0.7449 -0.0521 0.6791 11.00000 0.05 0.15 Q8 1 -0.0597 -0.2766 0.6652 11.00000 0.05 0.15 Q9 1 -0.0250 -0.1903 0.6330 11.00000 0.05 0.15 Q10 1 0.0433 0.4455 0.5577 11.00000 0.05 0.14 Q11 1 0.0138 0.4206 0.4956 11.00000 0.05 0.14 Q12 1 0.7584 0.0757 0.6995 11.00000 0.05 0.14 Q13 1 0.2611 0.4430 0.3750 11.00000 0.05 0.14 Q14 1 0.0455 0.4471 0.4494 11.00000 0.05 0.13 Q15 1 0.3405 0.0173 0.5018 11.00000 0.05 0.13 Q16 1 0.3468 0.5626 0.7056 11.00000 0.05 0.13 Q17 1 0.2478 0.4295 0.3211 11.00000 0.05 0.13 Q18 1 0.5006 -0.0365 0.7917 11.00000 0.05 0.13 Q19 1 0.0958 0.5308 0.4823 11.00000 0.05 0.13 Q20 1 0.3653 0.6322 0.4187 11.00000 0.05 0.13 Q21 1 0.2412 0.4733 0.4001 11.00000 0.05 0.12 Q22 1 0.3393 0.1116 0.5199 11.00000 0.05 0.12 Q23 1 0.3313 0.3809 0.4367 11.00000 0.05 0.12 Q24 1 0.4450 0.0462 0.7409 11.00000 0.05 0.12 Q25 1 0.3290 0.2548 0.7285 11.00000 0.05 0.12 Q26 1 0.0157 -0.1948 0.6573 11.00000 0.05 0.12 Q27 1 0.0158 0.2808 0.5089 11.00000 0.05 0.12 Q28 1 0.7756 0.2124 0.6843 11.00000 0.05 0.11 Q29 1 0.4628 0.5810 0.6869 11.00000 0.05 0.11 Q30 1 0.1234 0.4408 0.5684 11.00000 0.05 0.11 Q31 1 0.5823 0.0209 0.6971 11.00000 0.05 0.11 Q32 1 0.1342 0.4757 0.5624 11.00000 0.05 0.11 Q33 1 0.4571 -0.5180 0.7608 11.00000 0.05 0.11 Q34 1 0.7162 0.0657 0.7307 11.00000 0.05 0.11 Q35 1 0.5257 -0.2521 0.8051 11.00000 0.05 0.11 Q36 1 0.0186 -0.3784 0.6766 11.00000 0.05 0.11 Q37 1 0.6359 0.0063 0.6494 11.00000 0.05 0.11 Q38 1 0.4790 0.0251 0.5742 11.00000 0.05 0.11 Q39 1 0.0780 0.4376 0.5122 11.00000 0.05 0.11 Q40 1 0.3004 0.4402 0.6505 11.00000 0.05 0.11 Q41 1 0.4507 -0.4647 0.7423 11.00000 0.05 0.11 Q42 1 0.1800 0.4093 0.4247 11.00000 0.05 0.11 Q43 1 0.4831 -0.2118 0.8203 11.00000 0.05 0.11 Q44 1 0.0953 0.3507 0.5335 11.00000 0.05 0.11 Q45 1 0.3994 -0.1392 0.5451 11.00000 0.05 0.11 Q46 1 0.6090 0.1404 0.7035 11.00000 0.05 0.10 Q47 1 0.0999 -0.4475 0.5415 11.00000 0.05 0.10 Q48 1 0.7151 0.0586 0.6572 11.00000 0.05 0.10 Q49 1 0.7235 -0.1936 0.6984 11.00000 0.05 0.10 Q50 1 0.2679 0.3637 0.4766 11.00000 0.05 0.10 Q51 1 0.4663 0.1340 0.7290 11.00000 0.05 0.10 Q52 1 0.2945 0.0534 0.4569 11.00000 0.05 0.10 Q53 1 -0.2114 0.0841 0.4492 11.00000 0.05 0.10 Q54 1 -0.0108 -0.2627 0.5950 11.00000 0.05 0.10 Q55 1 0.1991 0.5953 0.4042 11.00000 0.05 0.10 Q56 1 0.3467 0.5251 0.4492 11.00000 0.05 0.10 Q57 1 0.5051 0.4661 0.6645 11.00000 0.05 0.10 Q58 1 0.0946 0.5922 0.4652 11.00000 0.05 0.10 Q59 1 0.0355 -0.4218 0.6869 11.00000 0.05 0.10 Q60 1 0.7025 -0.1074 0.7016 11.00000 0.05 0.10 Q61 1 0.0939 0.6650 0.3724 11.00000 0.05 0.10 Q62 1 0.4248 0.5257 0.6986 11.00000 0.05 0.09 Q63 1 0.1751 0.3645 0.6044 11.00000 0.05 0.09 Q64 1 0.5619 -0.3184 0.7794 11.00000 0.05 0.09 Q65 1 0.2076 0.3662 0.3525 11.00000 0.05 0.09 Q66 1 0.4055 0.1257 0.6969 11.00000 0.05 0.09 Q67 1 0.3791 0.5847 0.6178 11.00000 0.05 0.09 Q68 1 0.1819 -0.0787 0.4456 11.00000 0.05 0.09 Q69 1 0.8118 0.0575 0.7556 11.00000 0.05 0.09 Q70 1 0.8351 0.1450 0.7249 11.00000 0.05 0.09 Q71 1 0.8181 0.2297 0.7642 11.00000 0.05 0.09 Q72 1 0.2224 0.1513 0.4768 11.00000 0.05 0.09 Q73 1 0.2308 -0.0797 0.5116 11.00000 0.05 0.09 Q74 1 0.3069 0.7149 0.3520 11.00000 0.05 0.09 Q75 1 0.2772 0.1408 0.4887 11.00000 0.05 0.09 Q76 1 0.2543 0.3446 0.5531 11.00000 0.05 0.09 Q77 1 0.3028 0.7231 0.3828 11.00000 0.05 0.09 Q78 1 0.7805 -0.1106 0.7179 11.00000 0.05 0.09 Q79 1 0.4850 0.1613 0.7611 11.00000 0.05 0.09 Q80 1 -0.0233 -0.3840 0.6472 11.00000 0.05 0.09 Q81 1 0.5243 0.3414 0.4992 11.00000 0.05 0.09 Q82 1 0.3490 -0.0261 0.8105 11.00000 0.05 0.09 Q83 1 0.1831 0.5719 0.3514 11.00000 0.05 0.09 Q84 1 0.3927 -0.0006 0.4966 11.00000 0.05 0.09 Q85 1 0.5672 0.1433 0.5726 11.00000 0.05 0.08 Q86 1 0.5364 -0.1257 0.8198 11.00000 0.05 0.08 Q87 1 0.7134 -0.1891 0.6161 11.00000 0.05 0.08 Q88 1 0.8640 0.1711 0.6484 11.00000 0.05 0.08 Q89 1 0.8450 0.2688 0.7068 11.00000 0.05 0.08 Q90 1 0.2288 -0.1291 0.7290 11.00000 0.05 0.08 Q91 1 0.0809 0.4220 0.4029 11.00000 0.05 0.08 Q92 1 0.6699 0.3106 0.7369 11.00000 0.05 0.08 Q93 1 0.5013 0.2853 0.5128 11.00000 0.05 0.08 Q94 1 0.4196 -0.1083 0.5719 11.00000 0.05 0.08 Q95 1 0.1935 0.3112 0.5857 11.00000 0.05 0.08 Q96 1 0.0570 0.1731 0.5423 11.00000 0.05 0.08 Q97 1 0.6652 0.1386 0.6755 11.00000 0.05 0.08 Q98 1 0.1744 0.2370 0.4396 11.00000 0.05 0.08 Q99 1 0.2148 0.7908 0.4078 11.00000 0.05 0.08 Q100 1 0.2834 0.3245 0.3932 11.00000 0.05 0.08 Q101 1 0.1210 0.5889 0.3602 11.00000 0.05 0.08 Q102 1 0.1151 0.3367 0.3958 11.00000 0.05 0.08 Q103 1 0.0600 -0.2496 0.4513 11.00000 0.05 0.08 Q104 1 0.4941 0.2476 0.5964 11.00000 0.05 0.08 Q105 1 0.0937 0.2186 0.3790 11.00000 0.05 0.08 Q106 1 0.4130 0.1418 0.5612 11.00000 0.05 0.08 Q107 1 0.4844 0.4448 0.7169 11.00000 0.05 0.08 Q108 1 0.4377 0.5987 0.6242 11.00000 0.05 0.08 Q109 1 0.3450 -0.0471 0.7952 11.00000 0.05 0.08 Q110 1 0.3216 0.4512 0.4682 11.00000 0.05 0.08 Q111 1 0.9042 -0.1697 0.6691 11.00000 0.05 0.08 Q112 1 0.1132 0.2316 0.5153 11.00000 0.05 0.08 Q113 1 0.2545 -0.1932 0.5291 11.00000 0.05 0.08 Q114 1 0.2859 0.6796 0.4265 11.00000 0.05 0.08 Q115 1 0.2570 0.3272 0.5934 11.00000 0.05 0.08 Q116 1 0.2142 0.4533 0.4620 11.00000 0.05 0.08 Q117 1 0.3613 0.0172 0.7817 11.00000 0.05 0.08 Q118 1 0.1795 0.4970 0.4469 11.00000 0.05 0.08 Q119 1 0.7556 0.3449 0.7059 11.00000 0.05 0.08 Q120 1 0.4668 0.6633 0.7141 11.00000 0.05 0.08 Q121 1 0.3786 0.4393 0.6587 11.00000 0.05 0.08 Q122 1 0.2406 0.0255 0.4721 11.00000 0.05 0.08 Q123 1 -0.1939 0.3894 0.3818 11.00000 0.05 0.08 Q124 1 0.8386 0.1220 0.5957 11.00000 0.05 0.08 Q125 1 0.5141 -0.0735 0.6906 11.00000 0.05 0.08 Q126 1 0.6293 0.2429 0.7494 11.00000 0.05 0.08 Q127 1 0.2514 0.2901 0.4360 11.00000 0.05 0.08 Q128 1 0.4249 0.0376 0.5955 11.00000 0.05 0.07 Q129 1 0.1010 0.2063 0.6052 11.00000 0.05 0.07 Q130 1 -0.1345 0.1351 0.4503 11.00000 0.05 0.07 Q131 1 -0.2865 0.2683 0.4099 11.00000 0.05 0.07 Q132 1 0.2814 0.4784 0.4720 11.00000 0.05 0.07 Q133 1 0.2908 0.3428 0.3422 11.00000 0.05 0.07 Q134 1 0.5755 0.3865 0.7264 11.00000 0.05 0.07 Q135 1 0.9206 0.0378 0.7499 11.00000 0.05 0.07 Q136 1 0.2962 0.4242 0.5928 11.00000 0.05 0.07 Q137 1 0.4174 -0.1178 0.7480 11.00000 0.05 0.07 Q138 1 0.2784 0.5820 0.4980 11.00000 0.05 0.07 Q139 1 0.4810 -0.2627 0.6008 11.00000 0.05 0.07 Q140 1 0.1192 -0.1949 0.6801 11.00000 0.05 0.07 Q141 1 0.5593 0.0852 0.8054 11.00000 0.05 0.07 Q142 1 0.1606 0.4844 0.3333 11.00000 0.05 0.07 Q143 1 0.5625 -0.4945 0.7571 11.00000 0.05 0.07 Q144 1 0.3620 0.2777 0.4173 11.00000 0.05 0.07 Q145 1 0.3381 -0.1778 0.5657 11.00000 0.05 0.07 Q146 1 0.3324 -0.1042 0.7217 11.00000 0.05 0.07 Q147 1 0.3040 0.2515 0.5201 11.00000 0.05 0.07 Q148 1 0.6208 -0.1123 0.6157 11.00000 0.05 0.07 Q149 1 -0.1672 -0.0489 0.3639 11.00000 0.05 0.07 Q150 1 0.3024 0.5571 0.2812 11.00000 0.05 0.07 Q151 1 0.4056 -0.2909 0.5422 11.00000 0.05 0.07 Q152 1 0.6648 -0.0404 0.7370 11.00000 0.05 0.07 Q153 1 0.3798 0.5975 0.5010 11.00000 0.05 0.07 Q154 1 0.8395 0.1027 0.6389 11.00000 0.05 0.07 Q155 1 0.8356 -0.0117 0.7520 11.00000 0.05 0.07 Q156 1 0.3073 -0.0644 0.5493 11.00000 0.05 0.07 Q157 1 0.5167 0.0946 0.7190 11.00000 0.05 0.07 Q158 1 0.5130 0.2858 0.7417 11.00000 0.05 0.06 Q159 1 0.1526 -0.1350 0.4743 11.00000 0.05 0.06 Q160 1 0.4202 -0.0775 0.4657 11.00000 0.05 0.06 Q161 1 0.1740 0.6944 0.3497 11.00000 0.05 0.06 Q162 1 0.7853 -0.0207 0.5715 11.00000 0.05 0.06 Q163 1 0.1741 0.6060 0.5092 11.00000 0.05 0.06 Q164 1 0.1967 0.0142 0.4718 11.00000 0.05 0.06 Q165 1 0.3629 0.5278 0.3348 11.00000 0.05 0.06 Q166 1 0.3337 0.6480 0.3223 11.00000 0.05 0.06 Q167 1 0.5999 -0.1265 0.7262 11.00000 0.05 0.06 Q168 1 0.1644 0.4754 0.5213 11.00000 0.05 0.06 Q169 1 0.3654 0.3628 0.6839 11.00000 0.05 0.06 Q170 1 0.6787 0.0436 0.6961 11.00000 0.05 0.06 Q171 1 0.8318 0.1670 0.8045 11.00000 0.05 0.06 Q172 1 0.4840 0.3839 0.4024 11.00000 0.05 0.06 Q173 1 0.2681 0.5559 0.5958 11.00000 0.05 0.06 Q174 1 0.2458 0.5128 0.6030 11.00000 0.05 0.06 Q175 1 0.3046 0.1277 0.7442 11.00000 0.05 0.06 Q176 1 0.0734 0.2962 0.4281 11.00000 0.05 0.06 Q177 1 0.3848 -0.4336 0.7625 11.00000 0.05 0.06 Q178 1 0.4611 0.1129 0.5436 11.00000 0.05 0.06 Q179 1 0.3468 -0.2248 0.8128 11.00000 0.05 0.06 Q180 1 0.5359 -0.2999 0.8606 11.00000 0.05 0.06 Q181 1 0.7920 -0.1572 0.5935 11.00000 0.05 0.06 Q182 1 0.6835 0.2983 0.8203 11.00000 0.05 0.06 Q183 1 0.2717 0.0887 0.7435 11.00000 0.05 0.06 Q184 1 0.7007 0.0013 0.7931 11.00000 0.05 0.06 Q185 1 0.9016 0.2478 0.7494 11.00000 0.05 0.06 Q186 1 -0.2110 0.0825 0.3630 11.00000 0.05 0.06 Q187 1 0.4272 0.3008 0.4996 11.00000 0.05 0.05 Q188 1 0.4877 -0.2315 0.8838 11.00000 0.05 0.05 Q189 1 0.1568 0.1828 0.6012 11.00000 0.05 0.05 Q190 1 0.3822 -0.2703 0.5955 11.00000 0.05 0.05 Q191 1 0.3193 -0.1478 0.4566 11.00000 0.05 0.05 Q192 1 0.3952 0.2005 0.5938 11.00000 0.05 0.05 Q193 1 0.7347 0.2384 0.8252 11.00000 0.05 0.05 Q194 1 0.0225 0.6674 0.4199 11.00000 0.05 0.05 Q195 1 0.1327 -0.4138 0.5851 11.00000 0.05 0.05 Q196 1 0.5686 0.0026 0.6009 11.00000 0.05 0.05 Q197 1 0.0224 0.3440 0.5694 11.00000 0.05 0.05 Q198 1 0.1780 0.5308 0.3035 11.00000 0.05 0.05 Q199 1 0.4808 0.4146 0.5167 11.00000 0.05 0.05 Q200 1 0.4220 -0.2425 0.5118 11.00000 0.05 0.05 ; _shelx_res_checksum 95289 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 0.39207(19) 0.3505(2) 0.51914(9) 0.0605(6) Uani d . . . 1 . . N N1 0.3976(2) -0.1561(3) 0.55707(11) 0.0573(6) Uani d . . . 1 . . C C1 0.1971(4) 0.5466(5) 0.38595(16) 0.0811(11) Uani d . . . 1 . . H H1 0.154164 0.591327 0.355628 0.097 Uiso calc U . R 1 . . C C2 0.3049(4) 0.5235(5) 0.38328(16) 0.0762(10) Uani d . . . 1 . . H H2 0.334492 0.554085 0.351302 0.091 Uiso calc U . R 1 . . N N2 0.3300(2) 0.0759(3) 0.49906(11) 0.0580(6) Uani d . . . 1 . . O O2 0.51932(17) -0.1199(2) 0.63019(9) 0.0560(5) Uani d . . . 1 . . O O3 0.4527(2) 0.3709(3) 0.68035(11) 0.0709(7) Uani d . . . 1 . . N N3 0.1367(4) 0.3519(7) 0.56644(19) 0.1165(15) Uani d . . . 1 . . C C3 0.3697(3) 0.4561(4) 0.42709(14) 0.0619(8) Uani d . . . 1 . . H H3 0.442925 0.441321 0.425181 0.074 Uiso calc U . R 1 . . C C4 0.3247(2) 0.4105(3) 0.47391(13) 0.0529(7) Uani d . . . 1 . . O O4 0.3106(2) -0.0354(3) 0.75214(13) 0.0819(8) Uani d . . . 1 . . C C5 0.2167(3) 0.4355(4) 0.47799(14) 0.0615(8) Uani d . . . 1 . . O O5 0.47023(19) -0.1638(3) 0.76497(11) 0.0690(6) Uani d . . . 1 . . C C6 0.1521(3) 0.5048(5) 0.43258(18) 0.0768(10) Uani d . . . 1 . . H H6 0.079057 0.522174 0.434265 0.092 Uiso calc U . R 1 . . C C7 0.1718(3) 0.3904(6) 0.52726(18) 0.0793(10) Uani d . . . 1 . . C C8 0.3372(3) -0.0895(4) 0.51463(14) 0.0623(8) Uani d . . . 1 . . H H8 0.294304 -0.166265 0.492749 0.075 Uiso calc U . R 1 . . C C9 0.3936(2) 0.1792(3) 0.53062(12) 0.0503(6) Uani d . . . 1 . . C C10 0.4634(2) 0.1268(3) 0.57507(12) 0.0513(7) Uani d . . . 1 . . H H10 0.509295 0.202474 0.595711 0.062 Uiso calc U . R 1 . . C C11 0.4604(2) -0.0453(3) 0.58680(12) 0.0502(6) Uani d . . . 1 . . C C12 0.5991(2) -0.0247(3) 0.66125(12) 0.0514(7) Uani d . . . 1 . . C C13 0.7034(3) -0.0404(4) 0.64828(14) 0.0598(7) Uani d . . . 1 . . H H13 0.717908 -0.105928 0.61806 0.072 Uiso calc U . R 1 . . C C14 0.7846(3) 0.0408(5) 0.68010(16) 0.0688(9) Uani d . . . 1 . . H H14 0.854802 0.03186 0.671328 0.083 Uiso calc U . R 1 . . C C15 0.7630(3) 0.1366(5) 0.72547(16) 0.0715(9) Uani d . . . 1 . . H H15 0.818459 0.190605 0.747616 0.086 Uiso calc U . R 1 . . C C16 0.6581(3) 0.1510(4) 0.73747(14) 0.0648(8) Uani d . . . 1 . . H H16 0.643814 0.216153 0.767798 0.078 Uiso calc U . R 1 . . C C17 0.5741(2) 0.0717(3) 0.70585(12) 0.0526(7) Uani d . . . 1 . . C C18 0.4610(2) 0.0941(4) 0.71703(13) 0.0556(7) Uani d . . . 1 . . C C19 0.4047(3) -0.0374(4) 0.74542(14) 0.0596(7) Uani d . . . 1 . . C C20 0.4234(4) -0.2941(5) 0.7968(2) 0.0871(12) Uani d . . . 1 . . H H20A 0.358474 -0.336004 0.776451 0.131 Uiso calc U . R 1 . . H H20B 0.407212 -0.245949 0.831215 0.131 Uiso calc U . R 1 . . H H20C 0.473356 -0.387162 0.803997 0.131 Uiso calc U . R 1 . . C C21 0.4070(3) 0.2396(4) 0.70372(14) 0.0615(8) Uani d . . . 1 . . H H21 0.335923 0.248938 0.710994 0.074 Uiso calc U . R 1 . . C C22 0.3828(4) 0.5071(4) 0.65997(18) 0.0797(10) Uani d . . . 1 . . H H22A 0.361818 0.490965 0.621159 0.12 Uiso calc U . R 1 . . H H22B 0.419558 0.614902 0.665811 0.12 Uiso calc U . R 1 . . H H22C 0.31997 0.507075 0.67924 0.12 Uiso calc U . R 1 . . C C1_2 -0.0331(9) 0.0982(19) 0.4291(6) 0.123(3) Uani d U P D 0.5 A -1 O O2_2 0.0276(9) 0.0832(17) 0.3943(5) 0.154(4) Uani d U P D 0.5 A -1 C C3_2 0.0391(13) 0.007(3) 0.4730(7) 0.131(3) Uani d U P D 0.5 A -1 H H3A_2 0.054343 -0.106323 0.459476 0.158 Uiso calc U P R 0.5 A -1 H H3AB_2 0.106784 0.069029 0.478716 0.158 Uiso calc U P R 0.5 A -1 C C2_2 -0.1631(14) 0.218(3) 0.3635(6) 0.162(6) Uani d U P D 0.5 A -1 H H2A_2 -0.23627 0.25624 0.362548 0.194 Uiso calc U P R 0.5 A -1 H H2B_2 -0.118659 0.31247 0.354763 0.194 Uiso calc U P R 0.5 A -1 H H2C_2 -0.158992 0.127919 0.33698 0.194 Uiso calc U P R 0.5 A -1 O O1_2 -0.1288(8) 0.1592(15) 0.4143(4) 0.148(3) Uani d U P D 0.5 A -1 C C4_2 -0.0016(12) -0.011(2) 0.5257(6) 0.122(3) Uani d U P D 0.5 A -1 H H4A_2 -0.075623 -0.050412 0.519502 0.146 Uiso calc U P R 0.5 A -1 H H4AB_2 -0.001523 0.100339 0.543342 0.146 Uiso calc U P R 0.5 A -1 C C5_2 0.0604(13) -0.1323(14) 0.5634(4) 0.100(3) Uani d U P D 0.5 A -1 C C6_2 0.0940(14) -0.250(2) 0.6471(5) 0.137(5) Uani d U P D 0.5 A -1 H H6A_2 0.072642 -0.243242 0.683632 0.165 Uiso calc U P R 0.5 A -1 H H6B_2 0.079734 -0.363603 0.632557 0.165 Uiso calc U P R 0.5 A -1 H H6C_2 0.169498 -0.226202 0.648417 0.165 Uiso calc U P R 0.5 A -1 O O3_2 0.0369(10) -0.1322(11) 0.6135(3) 0.131(3) Uani d U P D 0.5 A -1 O O4_2 0.1021(9) -0.2453(11) 0.5408(3) 0.138(3) Uani d U P D 0.5 A -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 0.0705(13) 0.0453(10) 0.0621(12) -0.0048(9) -0.0079(10) 0.0055(9) N1 0.0621(15) 0.0447(12) 0.0637(15) -0.0060(11) 0.0004(12) -0.0023(11) C1 0.092(3) 0.071(2) 0.074(2) 0.000(2) -0.017(2) 0.0191(18) C2 0.092(3) 0.069(2) 0.066(2) -0.0092(19) 0.0038(18) 0.0141(17) N2 0.0594(14) 0.0519(12) 0.0603(14) -0.0016(11) -0.0032(11) -0.0025(11) O2 0.0594(12) 0.0457(9) 0.0609(12) -0.0039(9) -0.0024(9) 0.0048(9) O3 0.0746(15) 0.0517(11) 0.0905(16) 0.0010(10) 0.0273(13) 0.0101(11) N3 0.115(3) 0.144(4) 0.097(3) -0.023(3) 0.041(3) -0.006(3) C3 0.0674(19) 0.0535(15) 0.0656(18) -0.0054(14) 0.0118(15) 0.0012(14) C4 0.0584(16) 0.0406(12) 0.0584(16) -0.0001(12) 0.0004(13) 0.0012(12) O4 0.0608(14) 0.0764(15) 0.113(2) 0.0053(12) 0.0282(13) 0.0252(14) C5 0.0595(18) 0.0544(15) 0.0706(19) 0.0000(14) 0.0078(15) 0.0008(14) O5 0.0572(12) 0.0663(13) 0.0849(16) 0.0021(10) 0.0143(11) 0.0238(12) C6 0.063(2) 0.0665(19) 0.098(3) 0.0058(16) -0.0050(19) 0.0046(19) C7 0.071(2) 0.087(2) 0.082(2) -0.0049(19) 0.0178(19) -0.004(2) C8 0.0657(19) 0.0480(14) 0.070(2) -0.0060(13) -0.0049(15) -0.0047(14) C9 0.0527(15) 0.0444(13) 0.0546(15) -0.0013(12) 0.0096(12) -0.0004(12) C10 0.0527(15) 0.0455(13) 0.0545(15) -0.0043(12) 0.0010(12) 0.0005(12) C11 0.0497(14) 0.0463(13) 0.0550(15) -0.0012(11) 0.0073(12) -0.0002(12) C12 0.0503(15) 0.0452(13) 0.0580(16) -0.0026(11) 0.0027(12) 0.0074(12) C13 0.0568(17) 0.0568(16) 0.0664(18) 0.0028(13) 0.0100(14) 0.0067(14) C14 0.0506(17) 0.0715(19) 0.085(2) -0.0015(15) 0.0109(16) 0.0131(18) C15 0.0594(19) 0.076(2) 0.075(2) -0.0157(16) -0.0092(16) 0.0101(18) C16 0.066(2) 0.0631(17) 0.0635(18) -0.0091(15) 0.0016(15) -0.0003(15) C17 0.0547(16) 0.0456(13) 0.0574(16) -0.0027(12) 0.0063(12) 0.0051(12) C18 0.0553(16) 0.0512(15) 0.0616(17) -0.0040(13) 0.0125(13) 0.0028(13) C19 0.0559(17) 0.0569(16) 0.0668(18) 0.0006(13) 0.0110(14) 0.0045(14) C20 0.079(2) 0.079(2) 0.105(3) -0.001(2) 0.018(2) 0.038(2) C21 0.0623(18) 0.0556(16) 0.0692(19) -0.0008(14) 0.0191(15) 0.0015(14) C22 0.095(3) 0.0564(17) 0.091(3) 0.0111(18) 0.025(2) 0.0086(18) C1_2 0.107(6) 0.119(7) 0.133(7) 0.003(6) -0.026(5) 0.013(6) O2_2 0.123(7) 0.179(8) 0.155(7) 0.044(6) -0.009(5) -0.029(6) C3_2 0.120(8) 0.119(6) 0.150(6) 0.001(6) -0.008(6) -0.011(5) C2_2 0.157(12) 0.174(13) 0.147(10) 0.092(11) -0.013(10) 0.004(9) O1_2 0.128(6) 0.176(7) 0.133(6) 0.035(6) -0.011(5) 0.001(6) C4_2 0.137(8) 0.093(5) 0.124(5) -0.037(6) -0.035(6) 0.023(5) C5_2 0.133(7) 0.072(4) 0.096(5) 0.008(5) 0.018(5) 0.012(4) C6_2 0.199(13) 0.129(9) 0.082(6) 0.050(10) 0.004(8) 0.018(6) O3_2 0.185(8) 0.109(5) 0.098(4) 0.054(5) 0.018(5) -0.002(4) O4_2 0.183(8) 0.120(5) 0.114(5) 0.070(5) 0.025(5) 0.012(5) 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 C9 O1 C4 . . 119.0(2) ? C8 N1 C11 . . 115.1(2) ? C6 C1 C2 . . 120.7(3) ? C6 C1 H1 . . 119.7 ? C2 C1 H1 . . 119.7 ? C3 C2 C1 . . 120.8(4) ? C3 C2 H2 . . 119.6 ? C1 C2 H2 . . 119.6 ? C9 N2 C8 . . 113.9(3) ? C11 O2 C12 . . 119.3(2) ? C21 O3 C22 . . 116.4(3) ? C2 C3 C4 . . 118.9(3) ? C2 C3 H3 . . 120.5 ? C4 C3 H3 . . 120.5 ? C3 C4 C5 . . 121.3(3) ? C3 C4 O1 . . 118.4(3) ? C5 C4 O1 . . 120.1(3) ? C4 C5 C6 . . 118.6(3) ? C4 C5 C7 . . 120.5(3) ? C6 C5 C7 . . 120.8(3) ? C19 O5 C20 . . 116.1(3) ? C1 C6 C5 . . 119.6(4) ? C1 C6 H6 . . 120.2 ? C5 C6 H6 . . 120.2 ? N3 C7 C5 . . 178.9(5) ? N1 C8 N2 . . 127.9(3) ? N1 C8 H8 . . 116.1 ? N2 C8 H8 . . 116.1 ? N2 C9 O1 . . 119.0(3) ? N2 C9 C10 . . 124.5(3) ? O1 C9 C10 . . 116.4(2) ? C11 C10 C9 . . 115.1(3) ? C11 C10 H10 . . 122.4 ? C9 C10 H10 . . 122.4 ? N1 C11 O2 . . 112.7(2) ? N1 C11 C10 . . 123.4(3) ? O2 C11 C10 . . 123.9(3) ? C13 C12 C17 . . 122.0(3) ? C13 C12 O2 . . 117.7(3) ? C17 C12 O2 . . 120.1(3) ? C14 C13 C12 . . 119.5(3) ? C14 C13 H13 . . 120.3 ? C12 C13 H13 . . 120.3 ? C13 C14 C15 . . 120.2(3) ? C13 C14 H14 . . 119.9 ? C15 C14 H14 . . 119.9 ? C16 C15 C14 . . 119.2(3) ? C16 C15 H15 . . 120.4 ? C14 C15 H15 . . 120.4 ? C17 C16 C15 . . 121.9(3) ? C17 C16 H16 . . 119.0 ? C15 C16 H16 . . 119.0 ? C16 C17 C12 . . 117.1(3) ? C16 C17 C18 . . 122.0(3) ? C12 C17 C18 . . 120.9(3) ? C21 C18 C19 . . 116.8(3) ? C21 C18 C17 . . 121.4(3) ? C19 C18 C17 . . 121.8(3) ? O4 C19 O5 . . 122.1(3) ? O4 C19 C18 . . 125.8(3) ? O5 C19 C18 . . 112.1(3) ? O5 C20 H20A . . 109.5 ? O5 C20 H20B . . 109.5 ? H20A C20 H20B . . 109.5 ? O5 C20 H20C . . 109.5 ? H20A C20 H20C . . 109.5 ? H20B C20 H20C . . 109.5 ? O3 C21 C18 . . 121.6(3) ? O3 C21 H21 . . 119.2 ? C18 C21 H21 . . 119.2 ? O3 C22 H22A . . 109.5 ? O3 C22 H22B . . 109.5 ? H22A C22 H22B . . 109.5 ? O3 C22 H22C . . 109.5 ? H22A C22 H22C . . 109.5 ? H22B C22 H22C . . 109.5 ? O2_2 C1_2 O1_2 . . 118.4(12) ? O2_2 C1_2 C3_2 . . 94.5(10) ? O1_2 C1_2 C3_2 . . 146.4(12) ? C4_2 C3_2 C1_2 . . 115.9(10) ? C4_2 C3_2 H3A_2 . . 108.3 ? C1_2 C3_2 H3A_2 . . 108.3 ? C4_2 C3_2 H3AB_2 . . 108.3 ? C1_2 C3_2 H3AB_2 . . 108.3 ? H3A_2 C3_2 H3AB_2 . . 107.4 ? O1_2 C2_2 H2A_2 . . 109.5 ? O1_2 C2_2 H2B_2 . . 109.5 ? H2A_2 C2_2 H2B_2 . . 109.5 ? O1_2 C2_2 H2C_2 . . 109.5 ? H2A_2 C2_2 H2C_2 . . 109.5 ? H2B_2 C2_2 H2C_2 . . 109.5 ? C1_2 O1_2 C2_2 . . 124.6(12) ? C3_2 C4_2 C5_2 . . 113.9(10) ? C3_2 C4_2 H4A_2 . . 108.8 ? C5_2 C4_2 H4A_2 . . 108.8 ? C3_2 C4_2 H4AB_2 . . 108.8 ? C5_2 C4_2 H4AB_2 . . 108.8 ? H4A_2 C4_2 H4AB_2 . . 107.7 ? O4_2 C5_2 O3_2 . . 126.7(9) ? O4_2 C5_2 C4_2 . . 114.4(11) ? O3_2 C5_2 C4_2 . . 115.5(10) ? O3_2 C6_2 H6A_2 . . 109.5 ? O3_2 C6_2 H6B_2 . . 109.5 ? H6A_2 C6_2 H6B_2 . . 109.5 ? O3_2 C6_2 H6C_2 . . 109.5 ? H6A_2 C6_2 H6C_2 . . 109.5 ? H6B_2 C6_2 H6C_2 . . 109.5 ? C5_2 O3_2 C6_2 . . 113.9(10) ? 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 C9 . 1.363(3) ? O1 C4 . 1.390(4) ? N1 C8 . 1.316(4) ? N1 C11 . 1.326(4) ? C1 C6 . 1.363(6) ? C1 C2 . 1.370(6) ? C1 H1 . 0.93 ? C2 C3 . 1.370(5) ? C2 H2 . 0.93 ? N2 C9 . 1.316(4) ? N2 C8 . 1.342(4) ? O2 C11 . 1.349(3) ? O2 C12 . 1.396(3) ? O3 C21 . 1.330(4) ? O3 C22 . 1.427(4) ? N3 C7 . 1.135(6) ? C3 C4 . 1.374(5) ? C3 H3 . 0.93 ? C4 C5 . 1.381(5) ? O4 C19 . 1.207(4) ? C5 C6 . 1.401(5) ? C5 C7 . 1.425(5) ? O5 C19 . 1.334(4) ? O5 C20 . 1.441(4) ? C6 H6 . 0.93 ? C8 H8 . 0.93 ? C9 C10 . 1.374(4) ? C10 C11 . 1.371(4) ? C10 H10 . 0.93 ? C12 C13 . 1.382(4) ? C12 C17 . 1.385(4) ? C13 C14 . 1.362(5) ? C13 H13 . 0.93 ? C14 C15 . 1.385(6) ? C14 H14 . 0.93 ? C15 C16 . 1.381(5) ? C15 H15 . 0.93 ? C16 C17 . 1.377(4) ? C16 H16 . 0.93 ? C17 C18 . 1.482(4) ? C18 C21 . 1.339(5) ? C18 C19 . 1.461(4) ? C20 H20A . 0.96 ? C20 H20B . 0.96 ? C20 H20C . 0.96 ? C21 H21 . 0.93 ? C22 H22A . 0.96 ? C22 H22B . 0.96 ? C22 H22C . 0.96 ? C1_2 O2_2 . 1.206(9) ? C1_2 O1_2 . 1.301(9) ? C1_2 C3_2 . 1.499(9) ? C3_2 C4_2 . 1.440(9) ? C3_2 H3A_2 . 0.97 ? C3_2 H3AB_2 . 0.97 ? C2_2 O1_2 . 1.342(9) ? C2_2 H2A_2 . 0.96 ? C2_2 H2B_2 . 0.96 ? C2_2 H2C_2 . 0.96 ? C4_2 C5_2 . 1.474(9) ? C4_2 H4A_2 . 0.97 ? C4_2 H4AB_2 . 0.97 ? C5_2 O4_2 . 1.189(8) ? C5_2 O3_2 . 1.286(8) ? C6_2 O3_2 . 1.375(9) ? C6_2 H6A_2 . 0.96 ? C6_2 H6B_2 . 0.96 ? C6_2 H6C_2 . 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 C10 H10 O3 . 0.93 2.61 3.206(4) 122.6 ? C20 H20A O4 2_546 0.96 2.65 3.569(5) 159.7 ? C22 H22B O2 1_565 0.96 2.61 3.487(4) 151.8 ? C22 H22C O4 2_556 0.96 2.49 3.423(5) 164.7 ? C4_2 H4AB_2 N3 . 0.97 2.63 3.405(18) 136.9 ? 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 C6 C1 C2 C3 . . . . 0.8(6) ? C1 C2 C3 C4 . . . . 0.4(5) ? C2 C3 C4 C5 . . . . -1.7(5) ? C2 C3 C4 O1 . . . . -176.7(3) ? C9 O1 C4 C3 . . . . -104.7(3) ? C9 O1 C4 C5 . . . . 80.2(4) ? C3 C4 C5 C6 . . . . 1.7(5) ? O1 C4 C5 C6 . . . . 176.6(3) ? C3 C4 C5 C7 . . . . -178.8(3) ? O1 C4 C5 C7 . . . . -3.9(5) ? C2 C1 C6 C5 . . . . -0.8(6) ? C4 C5 C6 C1 . . . . -0.4(5) ? C7 C5 C6 C1 . . . . -179.9(4) ? C11 N1 C8 N2 . . . . -1.9(5) ? C9 N2 C8 N1 . . . . 1.2(5) ? C8 N2 C9 O1 . . . . -179.2(3) ? C8 N2 C9 C10 . . . . 1.2(5) ? C4 O1 C9 N2 . . . . -1.0(4) ? C4 O1 C9 C10 . . . . 178.6(3) ? N2 C9 C10 C11 . . . . -2.6(5) ? O1 C9 C10 C11 . . . . 177.8(3) ? C8 N1 C11 O2 . . . . 179.1(3) ? C8 N1 C11 C10 . . . . 0.2(5) ? C12 O2 C11 N1 . . . . 172.0(3) ? C12 O2 C11 C10 . . . . -9.2(4) ? C9 C10 C11 N1 . . . . 1.8(5) ? C9 C10 C11 O2 . . . . -177.0(3) ? C11 O2 C12 C13 . . . . -95.8(3) ? C11 O2 C12 C17 . . . . 88.7(3) ? C17 C12 C13 C14 . . . . 0.1(5) ? O2 C12 C13 C14 . . . . -175.4(3) ? C12 C13 C14 C15 . . . . 0.8(5) ? C13 C14 C15 C16 . . . . -1.1(5) ? C14 C15 C16 C17 . . . . 0.5(5) ? C15 C16 C17 C12 . . . . 0.3(5) ? C15 C16 C17 C18 . . . . -176.9(3) ? C13 C12 C17 C16 . . . . -0.6(4) ? O2 C12 C17 C16 . . . . 174.7(3) ? C13 C12 C17 C18 . . . . 176.7(3) ? O2 C12 C17 C18 . . . . -8.0(4) ? C16 C17 C18 C21 . . . . 75.0(4) ? C12 C17 C18 C21 . . . . -102.1(4) ? C16 C17 C18 C19 . . . . -102.0(4) ? C12 C17 C18 C19 . . . . 80.9(4) ? C20 O5 C19 O4 . . . . -2.7(5) ? C20 O5 C19 C18 . . . . 176.1(3) ? C21 C18 C19 O4 . . . . 9.2(5) ? C17 C18 C19 O4 . . . . -173.7(3) ? C21 C18 C19 O5 . . . . -169.5(3) ? C17 C18 C19 O5 . . . . 7.6(4) ? C22 O3 C21 C18 . . . . 170.2(3) ? C19 C18 C21 O3 . . . . 176.5(3) ? C17 C18 C21 O3 . . . . -0.6(5) ? O2_2 C1_2 C3_2 C4_2 . . . . -178.9(13) ? O1_2 C1_2 C3_2 C4_2 . . . . -11.(3) ? O2_2 C1_2 O1_2 C2_2 . . . . -5.(2) ? C3_2 C1_2 O1_2 C2_2 . . . . -171.(3) ? C1_2 C3_2 C4_2 C5_2 . . . . 167.5(19) ? C3_2 C4_2 C5_2 O4_2 . . . . -29.8(18) ? C3_2 C4_2 C5_2 O3_2 . . . . 169.6(12) ? O4_2 C5_2 O3_2 C6_2 . . . . 20.(3) ? C4_2 C5_2 O3_2 C6_2 . . . . 178.1(14) ?