#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:53:54 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247596.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_7247596 loop_ _publ_author_name 'Kawahata, Masatoshi' 'Yamamoto, Haruka' 'Tominaga, Masahide' 'Yamaguchi, Kentaro' _publ_section_title ; Multiple intermolecular interactions in guest inclusion by acyclic host compounds ; _journal_issue 44 _journal_name_full CrystEngComm _journal_page_first 6137 _journal_page_last 6143 _journal_paper_doi 10.1039/D3CE00775H _journal_volume 25 _journal_year 2023 _chemical_formula_sum 'C26 H30 N2 O6' _chemical_formula_weight 466.52 _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 geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-06-06 deposited with the CCDC. 2023-10-23 downloaded from the CCDC. ; _cell_angle_alpha 84.131(5) _cell_angle_beta 85.474(5) _cell_angle_gamma 72.254(5) _cell_formula_units_Z 2 _cell_length_a 7.1643(12) _cell_length_b 9.8755(16) _cell_length_c 17.073(3) _cell_measurement_reflns_used 9928 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 78.97 _cell_measurement_theta_min 4.72 _cell_volume 1143.0(3) _computing_cell_refinement 'SAINT (Bruker AXS, 2015)' _computing_data_collection 'APEX3 (Bruker AXS, 2015)' _computing_data_reduction 'SAINT (Bruker AXS, 2015)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'SHELXLE (H\"ubschle et al., 2011)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.24 _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.916 _diffrn_measurement_device_type 'BrukerD8 goniometer' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0312 _diffrn_reflns_av_unetI/netI 0.0225 _diffrn_reflns_Laue_measured_fraction_full 0.980 _diffrn_reflns_Laue_measured_fraction_max 0.916 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 16106 _diffrn_reflns_point_group_measured_fraction_full 0.980 _diffrn_reflns_point_group_measured_fraction_max 0.916 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 78.958 _diffrn_reflns_theta_min 4.717 _diffrn_source 'rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 0.792 _exptl_absorpt_correction_T_max 0.9424 _exptl_absorpt_correction_T_min 0.8698 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.356 _exptl_crystal_description prismatic _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.140 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.309 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 4521 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0362 _refine_ls_R_factor_gt 0.0342 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0412P)^2^+0.4022P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0905 _refine_ls_wR_factor_ref 0.0920 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4225 _reflns_number_total 4521 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00775h2.cif _cod_data_source_block 3a _cod_depositor_comments 'Adding full bibliography for 7247591--7247596.cif.' _cod_original_cell_volume 1142.9(3) _cod_database_code 7247596 _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_min 0.897 _shelx_estimated_absorpt_t_max 0.939 _shelx_res_file ; TITL dom1_p-1_a.res in P-1 v200924_tom1.res created by SHELXL-2018/3 at 08:01:42 on 08-Dec-2022 REM Old TITL dom1_p-1 in P-1 REM SHELXT solution in P-1: R1 0.139, Rweak 0.004, Alpha 0.036 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C28 N2 O4 CELL 1.54178 7.1643 9.8755 17.0725 84.131 85.474 72.254 ZERR 2.000 0.0012 0.0016 0.0028 0.005 0.005 0.005 LATT 1 SFAC C H N O UNIT 52 60 4 12 OMIT -4 -3 18 OMIT -2 -5 17 OMIT -3 -4 18 TEMP -173.000 SIZE 0.08 0.10 0.14 REM colourless prismatic L.S. 10 ACTA CONF WPDB -2 BOND $H LIST 4 FMAP 2 PLAN 10 WGHT 0.041200 0.402200 FVAR 1.08679 C1 1 0.352937 0.840777 0.271349 11.00000 0.01408 0.01258 = 0.01789 -0.00134 -0.00023 -0.00326 C2 1 0.550739 0.724050 0.256786 11.00000 0.01278 0.01244 = 0.01717 -0.00117 -0.00108 -0.00352 AFIX 23 H2A 2 0.612244 0.687384 0.307715 11.00000 -1.20000 H2B 2 0.640660 0.766334 0.222884 11.00000 -1.20000 AFIX 0 C3 1 0.520531 0.598763 0.216554 11.00000 0.01347 0.01294 = 0.01606 -0.00092 -0.00053 -0.00391 C4 1 0.376678 0.533576 0.267879 11.00000 0.01733 0.01413 = 0.01986 -0.00036 -0.00011 -0.00665 AFIX 23 H4A 2 0.354464 0.455980 0.241044 11.00000 -1.20000 H4B 2 0.433921 0.492425 0.319091 11.00000 -1.20000 AFIX 0 C5 1 0.180805 0.649062 0.281820 11.00000 0.01499 0.01737 = 0.02161 -0.00058 0.00261 -0.00717 AFIX 13 H5 2 0.090820 0.606335 0.316577 11.00000 -1.20000 AFIX 0 C6 1 0.216440 0.769686 0.322620 11.00000 0.01645 0.01684 = 0.01787 -0.00169 0.00248 -0.00466 AFIX 23 H6A 2 0.275970 0.730727 0.373688 11.00000 -1.20000 H6B 2 0.089308 0.842249 0.333478 11.00000 -1.20000 AFIX 0 C7 1 0.423222 0.661271 0.137887 11.00000 0.01535 0.01721 = 0.01649 -0.00154 -0.00151 -0.00474 AFIX 23 H7A 2 0.511158 0.704846 0.103611 11.00000 -1.20000 H7B 2 0.403246 0.583584 0.110418 11.00000 -1.20000 AFIX 0 C8 1 0.224625 0.774556 0.152013 11.00000 0.01431 0.01800 = 0.01870 -0.00003 -0.00361 -0.00400 AFIX 13 H8 2 0.165280 0.812445 0.100132 11.00000 -1.20000 AFIX 0 C9 1 0.255663 0.897500 0.192075 11.00000 0.01391 0.01432 = 0.02004 0.00080 -0.00134 -0.00277 AFIX 23 H9A 2 0.127769 0.970228 0.201430 11.00000 -1.20000 H9B 2 0.340299 0.943179 0.157224 11.00000 -1.20000 AFIX 0 C10 1 0.086011 0.708220 0.203594 11.00000 0.01390 0.02003 = 0.02546 -0.00219 -0.00142 -0.00675 AFIX 23 H10A 2 -0.041713 0.781192 0.212850 11.00000 -1.20000 H10B 2 0.062808 0.630636 0.177075 11.00000 -1.20000 AFIX 0 C11 1 0.389106 0.960222 0.313279 11.00000 0.01409 0.01236 = 0.02262 -0.00171 -0.00379 -0.00013 C12 1 0.507373 1.044824 0.278609 11.00000 0.01634 0.01312 = 0.02638 -0.00129 -0.00434 -0.00103 C13 1 0.541612 1.150781 0.319178 11.00000 0.02289 0.01546 = 0.03735 -0.00153 -0.00771 -0.00595 AFIX 43 H13 2 0.622762 1.204988 0.294918 11.00000 -1.20000 AFIX 0 C14 1 0.458754 1.177174 0.393930 11.00000 0.02902 0.01691 = 0.03472 -0.00730 -0.01294 -0.00200 AFIX 43 H14 2 0.481709 1.248878 0.421558 11.00000 -1.20000 AFIX 0 C15 1 0.342012 1.096833 0.427355 11.00000 0.02199 0.01958 = 0.02437 -0.00655 -0.00749 0.00366 C16 1 0.307244 0.990194 0.388351 11.00000 0.01764 0.01631 = 0.02303 -0.00277 -0.00396 0.00002 AFIX 43 H16 2 0.225923 0.936991 0.413647 11.00000 -1.20000 AFIX 0 C17 1 0.679094 1.114035 0.161713 11.00000 0.02223 0.02109 = 0.03723 0.00307 0.00080 -0.01182 AFIX 23 H17A 2 0.800874 1.108934 0.187104 11.00000 -1.20000 H17B 2 0.591875 1.213549 0.160390 11.00000 -1.20000 AFIX 0 C18 1 0.725927 1.066869 0.079746 11.00000 0.03545 0.03605 = 0.03664 0.00222 0.00606 -0.01854 AFIX 137 H18A 2 0.603758 1.076652 0.054515 11.00000 -1.50000 H18B 2 0.807079 0.966871 0.082156 11.00000 -1.50000 H18C 2 0.797531 1.126280 0.049036 11.00000 -1.50000 AFIX 0 C19 1 0.719886 0.486301 0.203230 11.00000 0.01485 0.01142 = 0.01885 -0.00149 -0.00038 -0.00536 C20 1 0.839996 0.411865 0.265944 11.00000 0.01730 0.01275 = 0.01855 -0.00173 0.00011 -0.00528 C21 1 1.023917 0.313399 0.251567 11.00000 0.01793 0.01523 = 0.02240 0.00040 -0.00268 -0.00294 AFIX 43 H21 2 1.100747 0.265133 0.294612 11.00000 -1.20000 AFIX 0 C22 1 1.094824 0.285717 0.175346 11.00000 0.01676 0.01378 = 0.02718 -0.00317 0.00247 -0.00250 AFIX 43 H22 2 1.220693 0.220470 0.165171 11.00000 -1.20000 AFIX 0 C23 1 0.977565 0.355535 0.114643 11.00000 0.02061 0.01504 = 0.02032 -0.00455 0.00373 -0.00693 C24 1 0.794141 0.453829 0.127577 11.00000 0.01751 0.01365 = 0.01937 -0.00164 -0.00070 -0.00612 AFIX 43 H24 2 0.718390 0.499530 0.083800 11.00000 -1.20000 AFIX 0 C25 1 0.890639 0.370256 0.404744 11.00000 0.02095 0.02152 = 0.01906 0.00295 -0.00514 -0.00374 AFIX 23 H25A 2 1.017637 0.391521 0.398112 11.00000 -1.20000 H25B 2 0.916818 0.265655 0.406262 11.00000 -1.20000 AFIX 0 C26 1 0.782803 0.425107 0.479524 11.00000 0.02928 0.03358 = 0.01832 0.00084 -0.00221 -0.00834 AFIX 137 H26A 2 0.749514 0.529369 0.475816 11.00000 -1.50000 H26B 2 0.866242 0.384642 0.524109 11.00000 -1.50000 H26C 2 0.662214 0.397140 0.487493 11.00000 -1.50000 AFIX 0 N1 3 0.248486 1.123927 0.505904 11.00000 0.02682 0.02824 = 0.02677 -0.01160 -0.01016 0.00656 N2 3 1.048037 0.325511 0.033854 11.00000 0.02689 0.01857 = 0.02367 -0.00539 0.00563 -0.00645 O1 4 0.273004 1.222097 0.538783 11.00000 0.06443 0.03189 = 0.03513 -0.01879 -0.01088 -0.00258 O2 4 0.149912 1.048491 0.535608 11.00000 0.03401 0.05887 = 0.02931 -0.01850 0.00511 -0.01288 O3 4 0.582735 1.018758 0.204506 11.00000 0.02185 0.01639 = 0.02817 -0.00102 0.00290 -0.00937 O4 4 1.219502 0.253162 0.022331 11.00000 0.03432 0.04132 = 0.03324 -0.00618 0.01280 0.00879 O5 4 0.933326 0.373417 -0.019052 11.00000 0.03389 0.03299 = 0.02069 -0.00812 0.00117 -0.01340 O6 4 0.768533 0.440354 0.340467 11.00000 0.01916 0.01838 = 0.01516 -0.00045 -0.00186 -0.00003 HKLF 4 REM dom1_p-1_a.res in P-1 REM wR2 = 0.0920, GooF = S = 1.055, Restrained GooF = 1.055 for all data REM R1 = 0.0342 for 4225 Fo > 4sig(Fo) and 0.0362 for all 4521 data REM 309 parameters refined using 0 restraints END WGHT 0.0412 0.4022 REM Highest difference peak 0.309, deepest hole -0.216, 1-sigma level 0.038 Q1 1 0.4572 0.5632 0.2422 11.00000 0.05 0.31 Q2 1 0.1551 0.7417 0.1782 11.00000 0.05 0.29 Q3 1 0.6217 0.5409 0.2094 11.00000 0.05 0.27 Q4 1 0.5324 0.6585 0.2366 11.00000 0.05 0.27 Q5 1 0.3719 0.8984 0.2946 11.00000 0.05 0.26 Q6 1 0.1960 0.7124 0.2980 11.00000 0.05 0.25 Q7 1 0.4519 0.7870 0.2642 11.00000 0.05 0.25 Q8 1 0.2394 0.8337 0.1707 11.00000 0.05 0.25 Q9 1 0.2894 0.8100 0.2957 11.00000 0.05 0.24 Q10 1 0.3200 0.7184 0.1485 11.00000 0.05 0.24 ; _shelx_res_checksum 45332 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 C1 C 0.35294(14) 0.84078(10) 0.27135(6) 0.0150(2) Uani 1 1 d . . . . . C2 C 0.55074(14) 0.72405(10) 0.25679(6) 0.0142(2) Uani 1 1 d . . . . . H2A H 0.612244 0.687384 0.307715 0.017 Uiso 1 1 calc R U . . . H2B H 0.640660 0.766334 0.222884 0.017 Uiso 1 1 calc R U . . . C3 C 0.52053(14) 0.59876(10) 0.21655(6) 0.0142(2) Uani 1 1 d . . . . . C4 C 0.37668(15) 0.53358(10) 0.26788(6) 0.0168(2) Uani 1 1 d . . . . . H4A H 0.354464 0.455980 0.241044 0.020 Uiso 1 1 calc R U . . . H4B H 0.433921 0.492425 0.319091 0.020 Uiso 1 1 calc R U . . . C5 C 0.18081(14) 0.64906(11) 0.28182(6) 0.0177(2) Uani 1 1 d . . . . . H5 H 0.090820 0.606335 0.316577 0.021 Uiso 1 1 calc R U . . . C6 C 0.21644(15) 0.76969(11) 0.32262(6) 0.0173(2) Uani 1 1 d . . . . . H6A H 0.275970 0.730727 0.373688 0.021 Uiso 1 1 calc R U . . . H6B H 0.089308 0.842249 0.333478 0.021 Uiso 1 1 calc R U . . . C7 C 0.42322(14) 0.66127(11) 0.13789(6) 0.0163(2) Uani 1 1 d . . . . . H7A H 0.511158 0.704846 0.103611 0.020 Uiso 1 1 calc R U . . . H7B H 0.403246 0.583584 0.110418 0.020 Uiso 1 1 calc R U . . . C8 C 0.22462(14) 0.77456(11) 0.15201(6) 0.0171(2) Uani 1 1 d . . . . . H8 H 0.165280 0.812445 0.100132 0.021 Uiso 1 1 calc R U . . . C9 C 0.25566(14) 0.89750(10) 0.19207(6) 0.0166(2) Uani 1 1 d . . . . . H9A H 0.127769 0.970228 0.201430 0.020 Uiso 1 1 calc R U . . . H9B H 0.340299 0.943179 0.157224 0.020 Uiso 1 1 calc R U . . . C10 C 0.08601(15) 0.70822(11) 0.20359(6) 0.0194(2) Uani 1 1 d . . . . . H10A H -0.041713 0.781192 0.212850 0.023 Uiso 1 1 calc R U . . . H10B H 0.062808 0.630636 0.177075 0.023 Uiso 1 1 calc R U . . . C11 C 0.38911(14) 0.96022(10) 0.31328(6) 0.0170(2) Uani 1 1 d . . . . . C12 C 0.50737(15) 1.04482(11) 0.27861(7) 0.0192(2) Uani 1 1 d . . . . . C13 C 0.54161(17) 1.15078(11) 0.31918(7) 0.0249(2) Uani 1 1 d . . . . . H13 H 0.622762 1.204988 0.294918 0.030 Uiso 1 1 calc R U . . . C14 C 0.45875(17) 1.17717(12) 0.39393(7) 0.0270(3) Uani 1 1 d . . . . . H14 H 0.481709 1.248878 0.421558 0.032 Uiso 1 1 calc R U . . . C15 C 0.34201(16) 1.09683(12) 0.42736(7) 0.0235(2) Uani 1 1 d . . . . . C16 C 0.30724(15) 0.99019(11) 0.38835(6) 0.0199(2) Uani 1 1 d . . . . . H16 H 0.225923 0.936991 0.413647 0.024 Uiso 1 1 calc R U . . . C17 C 0.67909(17) 1.11404(12) 0.16171(7) 0.0262(3) Uani 1 1 d . . . . . H17A H 0.800874 1.108934 0.187104 0.031 Uiso 1 1 calc R U . . . H17B H 0.591875 1.213549 0.160390 0.031 Uiso 1 1 calc R U . . . C18 C 0.7259(2) 1.06687(15) 0.07975(8) 0.0351(3) Uani 1 1 d . . . . . H18A H 0.603758 1.076652 0.054515 0.053 Uiso 1 1 calc R U . . . H18B H 0.807079 0.966871 0.082156 0.053 Uiso 1 1 calc R U . . . H18C H 0.797531 1.126280 0.049036 0.053 Uiso 1 1 calc R U . . . C19 C 0.71989(14) 0.48630(10) 0.20323(6) 0.0147(2) Uani 1 1 d . . . . . C20 C 0.84000(15) 0.41187(10) 0.26594(6) 0.0160(2) Uani 1 1 d . . . . . C21 C 1.02392(15) 0.31340(11) 0.25157(6) 0.0190(2) Uani 1 1 d . . . . . H21 H 1.100747 0.265133 0.294612 0.023 Uiso 1 1 calc R U . . . C22 C 1.09482(15) 0.28572(11) 0.17535(7) 0.0198(2) Uani 1 1 d . . . . . H22 H 1.220693 0.220470 0.165171 0.024 Uiso 1 1 calc R U . . . C23 C 0.97757(15) 0.35553(11) 0.11464(6) 0.0183(2) Uani 1 1 d . . . . . C24 C 0.79414(15) 0.45383(10) 0.12758(6) 0.0165(2) Uani 1 1 d . . . . . H24 H 0.718390 0.499530 0.083800 0.020 Uiso 1 1 calc R U . . . C25 C 0.89064(16) 0.37026(12) 0.40474(6) 0.0212(2) Uani 1 1 d . . . . . H25A H 1.017637 0.391521 0.398112 0.025 Uiso 1 1 calc R U . . . H25B H 0.916818 0.265655 0.406262 0.025 Uiso 1 1 calc R U . . . C26 C 0.78280(18) 0.42511(13) 0.47952(7) 0.0275(3) Uani 1 1 d . . . . . H26A H 0.749514 0.529369 0.475816 0.041 Uiso 1 1 calc R U . . . H26B H 0.866242 0.384642 0.524109 0.041 Uiso 1 1 calc R U . . . H26C H 0.662214 0.397140 0.487493 0.041 Uiso 1 1 calc R U . . . N1 N 0.24849(15) 1.12393(11) 0.50590(6) 0.0294(2) Uani 1 1 d . . . . . N2 N 1.04804(14) 0.32551(10) 0.03385(6) 0.0232(2) Uani 1 1 d . . . . . O1 O 0.27300(17) 1.22210(10) 0.53878(6) 0.0449(3) Uani 1 1 d . . . . . O2 O 0.14991(14) 1.04849(12) 0.53561(6) 0.0403(2) Uani 1 1 d . . . . . O3 O 0.58273(11) 1.01876(8) 0.20451(5) 0.02161(18) Uani 1 1 d . . . . . O4 O 1.21950(14) 0.25316(11) 0.02233(6) 0.0414(3) Uani 1 1 d . . . . . O5 O 0.93333(13) 0.37342(9) -0.01905(5) 0.02814(19) Uani 1 1 d . . . . . O6 O 0.76853(11) 0.44035(8) 0.34047(4) 0.01884(17) Uani 1 1 d . . . . . 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 C1 0.0141(5) 0.0126(4) 0.0179(5) -0.0013(4) -0.0002(4) -0.0033(4) C2 0.0128(4) 0.0124(4) 0.0172(5) -0.0012(4) -0.0011(4) -0.0035(4) C3 0.0135(4) 0.0129(4) 0.0161(5) -0.0009(4) -0.0005(4) -0.0039(4) C4 0.0173(5) 0.0141(5) 0.0199(5) -0.0004(4) -0.0001(4) -0.0066(4) C5 0.0150(5) 0.0174(5) 0.0216(5) -0.0006(4) 0.0026(4) -0.0072(4) C6 0.0165(5) 0.0168(5) 0.0179(5) -0.0017(4) 0.0025(4) -0.0047(4) C7 0.0154(5) 0.0172(5) 0.0165(5) -0.0015(4) -0.0015(4) -0.0047(4) C8 0.0143(5) 0.0180(5) 0.0187(5) 0.0000(4) -0.0036(4) -0.0040(4) C9 0.0139(5) 0.0143(5) 0.0200(5) 0.0008(4) -0.0013(4) -0.0028(4) C10 0.0139(5) 0.0200(5) 0.0255(5) -0.0022(4) -0.0014(4) -0.0068(4) C11 0.0141(5) 0.0124(4) 0.0226(5) -0.0017(4) -0.0038(4) -0.0001(4) C12 0.0163(5) 0.0131(5) 0.0264(6) -0.0013(4) -0.0043(4) -0.0010(4) C13 0.0229(5) 0.0155(5) 0.0374(7) -0.0015(4) -0.0077(5) -0.0059(4) C14 0.0290(6) 0.0169(5) 0.0347(7) -0.0073(4) -0.0129(5) -0.0020(4) C15 0.0220(5) 0.0196(5) 0.0244(6) -0.0065(4) -0.0075(4) 0.0037(4) C16 0.0176(5) 0.0163(5) 0.0230(5) -0.0028(4) -0.0040(4) 0.0000(4) C17 0.0222(5) 0.0211(5) 0.0372(7) 0.0031(5) 0.0008(5) -0.0118(4) C18 0.0354(7) 0.0360(7) 0.0366(7) 0.0022(5) 0.0061(5) -0.0185(6) C19 0.0148(5) 0.0114(4) 0.0189(5) -0.0015(4) -0.0004(4) -0.0054(4) C20 0.0173(5) 0.0127(4) 0.0185(5) -0.0017(4) 0.0001(4) -0.0053(4) C21 0.0179(5) 0.0152(5) 0.0224(5) 0.0004(4) -0.0027(4) -0.0029(4) C22 0.0168(5) 0.0138(5) 0.0272(6) -0.0032(4) 0.0025(4) -0.0025(4) C23 0.0206(5) 0.0150(5) 0.0203(5) -0.0046(4) 0.0037(4) -0.0069(4) C24 0.0175(5) 0.0136(5) 0.0194(5) -0.0016(4) -0.0007(4) -0.0061(4) C25 0.0210(5) 0.0215(5) 0.0191(5) 0.0030(4) -0.0051(4) -0.0037(4) C26 0.0293(6) 0.0336(6) 0.0183(5) 0.0008(5) -0.0022(4) -0.0083(5) N1 0.0268(5) 0.0282(5) 0.0268(5) -0.0116(4) -0.0102(4) 0.0066(4) N2 0.0269(5) 0.0186(4) 0.0237(5) -0.0054(4) 0.0056(4) -0.0064(4) O1 0.0644(7) 0.0319(5) 0.0351(5) -0.0188(4) -0.0109(5) -0.0026(5) O2 0.0340(5) 0.0589(6) 0.0293(5) -0.0185(4) 0.0051(4) -0.0129(5) O3 0.0218(4) 0.0164(4) 0.0282(4) -0.0010(3) 0.0029(3) -0.0094(3) O4 0.0343(5) 0.0413(5) 0.0332(5) -0.0062(4) 0.0128(4) 0.0088(4) O5 0.0339(4) 0.0330(4) 0.0207(4) -0.0081(3) 0.0012(3) -0.0134(4) O6 0.0192(4) 0.0184(4) 0.0152(4) -0.0004(3) -0.0019(3) 0.0000(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C1 C6 110.93(8) . . ? C11 C1 C9 111.88(8) . . ? C6 C1 C9 107.37(8) . . ? C11 C1 C2 109.40(8) . . ? C6 C1 C2 107.59(8) . . ? C9 C1 C2 109.56(8) . . ? C1 C2 C3 111.23(8) . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2B 109.4 . . ? C3 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C19 C3 C7 111.56(8) . . ? C19 C3 C4 111.10(8) . . ? C7 C3 C4 107.24(8) . . ? C19 C3 C2 109.33(8) . . ? C7 C3 C2 107.45(8) . . ? C4 C3 C2 110.08(8) . . ? C5 C4 C3 109.91(8) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C10 C5 C6 109.84(8) . . ? C10 C5 C4 110.22(8) . . ? C6 C5 C4 109.44(8) . . ? C10 C5 H5 109.1 . . ? C6 C5 H5 109.1 . . ? C4 C5 H5 109.1 . . ? C5 C6 C1 111.49(8) . . ? C5 C6 H6A 109.3 . . ? C1 C6 H6A 109.3 . . ? C5 C6 H6B 109.3 . . ? C1 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C3 111.02(8) . . ? C8 C7 H7A 109.4 . . ? C3 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C3 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C10 C8 C9 110.00(8) . . ? C10 C8 C7 110.04(8) . . ? C9 C8 C7 109.63(8) . . ? C10 C8 H8 109.1 . . ? C9 C8 H8 109.1 . . ? C7 C8 H8 109.1 . . ? C8 C9 C1 110.02(8) . . ? C8 C9 H9A 109.7 . . ? C1 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C1 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C5 C10 C8 108.16(8) . . ? C5 C10 H10A 110.1 . . ? C8 C10 H10A 110.1 . . ? C5 C10 H10B 110.1 . . ? C8 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? C16 C11 C12 116.39(9) . . ? C16 C11 C1 120.94(9) . . ? C12 C11 C1 122.66(9) . . ? O3 C12 C13 122.10(10) . . ? O3 C12 C11 116.57(9) . . ? C13 C12 C11 121.33(10) . . ? C14 C13 C12 120.73(11) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 118.17(10) . . ? C15 C14 H14 120.9 . . ? C13 C14 H14 120.9 . . ? C14 C15 C16 122.06(11) . . ? C14 C15 N1 119.64(10) . . ? C16 C15 N1 118.29(11) . . ? C11 C16 C15 121.31(10) . . ? C11 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? O3 C17 C18 106.64(9) . . ? O3 C17 H17A 110.4 . . ? C18 C17 H17A 110.4 . . ? O3 C17 H17B 110.4 . . ? C18 C17 H17B 110.4 . . ? H17A C17 H17B 108.6 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 116.24(9) . . ? C24 C19 C3 120.73(9) . . ? C20 C19 C3 123.02(9) . . ? O6 C20 C21 121.30(9) . . ? O6 C20 C19 117.15(9) . . ? C21 C20 C19 121.55(9) . . ? C22 C21 C20 120.63(10) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 C21 117.98(9) . . ? C23 C22 H22 121.0 . . ? C21 C22 H22 121.0 . . ? C22 C23 C24 122.35(10) . . ? C22 C23 N2 118.81(9) . . ? C24 C23 N2 118.84(10) . . ? C19 C24 C23 121.23(10) . . ? C19 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? O6 C25 C26 107.48(9) . . ? O6 C25 H25A 110.2 . . ? C26 C25 H25A 110.2 . . ? O6 C25 H25B 110.2 . . ? C26 C25 H25B 110.2 . . ? H25A C25 H25B 108.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O2 N1 O1 123.28(11) . . ? O2 N1 C15 118.65(10) . . ? O1 N1 C15 118.07(11) . . ? O5 N2 O4 123.42(10) . . ? O5 N2 C23 118.40(9) . . ? O4 N2 C23 118.18(10) . . ? C12 O3 C17 119.28(8) . . ? C20 O6 C25 118.11(8) . . ? 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 C1 C11 1.5360(14) . ? C1 C6 1.5405(13) . ? C1 C9 1.5450(14) . ? C1 C2 1.5511(13) . ? C2 C3 1.5524(13) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C19 1.5357(13) . ? C3 C7 1.5449(13) . ? C3 C4 1.5463(13) . ? C4 C5 1.5342(14) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.5257(15) . ? C5 C6 1.5338(14) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5378(13) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.5269(14) . ? C8 C9 1.5329(14) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.3883(15) . ? C11 C12 1.4204(15) . ? C12 O3 1.3537(14) . ? C12 C13 1.4022(15) . ? C13 C14 1.3796(18) . ? C13 H13 0.9500 . ? C14 C15 1.3752(18) . ? C14 H14 0.9500 . ? C15 C16 1.3943(15) . ? C15 N1 1.4633(15) . ? C16 H16 0.9500 . ? C17 O3 1.4393(13) . ? C17 C18 1.5006(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C24 1.3879(14) . ? C19 C20 1.4234(14) . ? C20 O6 1.3574(13) . ? C20 C21 1.3996(14) . ? C21 C22 1.3820(15) . ? C21 H21 0.9500 . ? C22 C23 1.3760(15) . ? C22 H22 0.9500 . ? C23 C24 1.3922(14) . ? C23 N2 1.4587(14) . ? C24 H24 0.9500 . ? C25 O6 1.4407(12) . ? C25 C26 1.5003(16) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? N1 O2 1.2239(15) . ? N1 O1 1.2315(14) . ? N2 O5 1.2279(13) . ? N2 O4 1.2304(13) . ? 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 C11 C1 C2 C3 178.39(8) . . . . ? C6 C1 C2 C3 57.80(10) . . . . ? C9 C1 C2 C3 -58.63(10) . . . . ? C1 C2 C3 C19 179.90(8) . . . . ? C1 C2 C3 C7 58.67(10) . . . . ? C1 C2 C3 C4 -57.80(10) . . . . ? C19 C3 C4 C5 178.64(8) . . . . ? C7 C3 C4 C5 -59.21(10) . . . . ? C2 C3 C4 C5 57.39(10) . . . . ? C3 C4 C5 C10 62.15(10) . . . . ? C3 C4 C5 C6 -58.75(11) . . . . ? C10 C5 C6 C1 -59.90(10) . . . . ? C4 C5 C6 C1 61.23(11) . . . . ? C11 C1 C6 C5 -179.39(8) . . . . ? C9 C1 C6 C5 58.09(10) . . . . ? C2 C1 C6 C5 -59.77(10) . . . . ? C19 C3 C7 C8 -179.53(8) . . . . ? C4 C3 C7 C8 58.60(10) . . . . ? C2 C3 C7 C8 -59.72(10) . . . . ? C3 C7 C8 C10 -60.13(10) . . . . ? C3 C7 C8 C9 60.97(10) . . . . ? C10 C8 C9 C1 62.10(10) . . . . ? C7 C8 C9 C1 -59.03(10) . . . . ? C11 C1 C9 C8 179.36(8) . . . . ? C6 C1 C9 C8 -58.71(10) . . . . ? C2 C1 C9 C8 57.85(10) . . . . ? C6 C5 C10 C8 59.70(10) . . . . ? C4 C5 C10 C8 -60.96(10) . . . . ? C9 C8 C10 C5 -61.35(10) . . . . ? C7 C8 C10 C5 59.53(11) . . . . ? C6 C1 C11 C16 1.45(13) . . . . ? C9 C1 C11 C16 121.32(10) . . . . ? C2 C1 C11 C16 -117.08(10) . . . . ? C6 C1 C11 C12 -179.00(9) . . . . ? C9 C1 C11 C12 -59.13(12) . . . . ? C2 C1 C11 C12 62.47(12) . . . . ? C16 C11 C12 O3 -178.12(8) . . . . ? C1 C11 C12 O3 2.32(14) . . . . ? C16 C11 C12 C13 1.17(14) . . . . ? C1 C11 C12 C13 -178.40(9) . . . . ? O3 C12 C13 C14 178.39(10) . . . . ? C11 C12 C13 C14 -0.86(16) . . . . ? C12 C13 C14 C15 -0.01(16) . . . . ? C13 C14 C15 C16 0.53(16) . . . . ? C13 C14 C15 N1 -178.75(10) . . . . ? C12 C11 C16 C15 -0.66(14) . . . . ? C1 C11 C16 C15 178.91(9) . . . . ? C14 C15 C16 C11 -0.18(16) . . . . ? N1 C15 C16 C11 179.11(9) . . . . ? C7 C3 C19 C24 1.31(12) . . . . ? C4 C3 C19 C24 120.92(10) . . . . ? C2 C3 C19 C24 -117.39(10) . . . . ? C7 C3 C19 C20 -179.85(8) . . . . ? C4 C3 C19 C20 -60.24(12) . . . . ? C2 C3 C19 C20 61.45(11) . . . . ? C24 C19 C20 O6 -178.92(8) . . . . ? C3 C19 C20 O6 2.19(14) . . . . ? C24 C19 C20 C21 1.04(14) . . . . ? C3 C19 C20 C21 -177.85(9) . . . . ? O6 C20 C21 C22 -179.89(9) . . . . ? C19 C20 C21 C22 0.15(15) . . . . ? C20 C21 C22 C23 -1.31(15) . . . . ? C21 C22 C23 C24 1.30(15) . . . . ? C21 C22 C23 N2 -178.72(9) . . . . ? C20 C19 C24 C23 -1.07(14) . . . . ? C3 C19 C24 C23 177.85(9) . . . . ? C22 C23 C24 C19 -0.08(15) . . . . ? N2 C23 C24 C19 179.94(9) . . . . ? C14 C15 N1 O2 -177.85(10) . . . . ? C16 C15 N1 O2 2.85(15) . . . . ? C14 C15 N1 O1 2.25(15) . . . . ? C16 C15 N1 O1 -177.05(10) . . . . ? C22 C23 N2 O5 170.60(9) . . . . ? C24 C23 N2 O5 -9.42(14) . . . . ? C22 C23 N2 O4 -9.26(15) . . . . ? C24 C23 N2 O4 170.71(10) . . . . ? C13 C12 O3 C17 -8.41(14) . . . . ? C11 C12 O3 C17 170.87(9) . . . . ? C18 C17 O3 C12 -173.91(9) . . . . ? C21 C20 O6 C25 2.31(14) . . . . ? C19 C20 O6 C25 -177.73(8) . . . . ? C26 C25 O6 C20 177.22(9) . . . . ?