#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:53:54 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247592.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_7247592 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 'C25 H28 N2 O8' _chemical_formula_weight 484.49 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _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 95.120(4) _cell_angle_beta 94.102(5) _cell_angle_gamma 99.743(4) _cell_formula_units_Z 2 _cell_length_a 7.0715(10) _cell_length_b 10.4603(14) _cell_length_c 15.710(2) _cell_measurement_reflns_used 9876 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 79.63 _cell_measurement_theta_min 2.84 _cell_volume 1136.3(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 0.947 _diffrn_measured_fraction_theta_max 0.896 _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 0.0356 _diffrn_reflns_av_unetI/netI 0.0306 _diffrn_reflns_Laue_measured_fraction_full 0.947 _diffrn_reflns_Laue_measured_fraction_max 0.896 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 14281 _diffrn_reflns_point_group_measured_fraction_full 0.947 _diffrn_reflns_point_group_measured_fraction_max 0.896 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 79.614 _diffrn_reflns_theta_min 4.311 _diffrn_source 'rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 0.888 _exptl_absorpt_correction_T_max 0.9288 _exptl_absorpt_correction_T_min 0.7546 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.416 _exptl_crystal_description prismatic _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.280 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 372 _refine_ls_number_reflns 4426 _refine_ls_number_restraints 24 _refine_ls_restrained_S_all 1.134 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0462 _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^)+(0.0663P)^2^+0.5634P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1347 _refine_ls_wR_factor_ref 0.1389 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3956 _reflns_number_total 4426 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00775h2.cif _cod_data_source_block 1c _cod_depositor_comments 'Adding full bibliography for 7247591--7247596.cif.' _cod_database_code 7247592 _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 0.901 _shelx_estimated_absorpt_t_max 0.916 _shelx_res_file ; TITL P-1_a.res in P-1 P-1_a.res created by SHELXL-2018/3 at 08:08:00 on 15-Dec-2022 REM Old TITL P-1 in P-1 REM SHELXT solution in P-1: R1 0.166, Rweak 0.035, Alpha 0.042 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C28 O7 CELL 1.54178 7.0715 10.4603 15.7099 95.120 94.102 99.743 ZERR 2.000 0.0010 0.0014 0.0022 0.004 0.005 0.004 LATT 1 SFAC C H N O UNIT 50 56 4 16 OMIT -3 -11 5 OMIT -4 -10 5 OMIT -4 -10 6 OMIT -3 -11 4 OMIT -3 -11 2 OMIT -3 -11 3 OMIT -3 -11 6 OMIT -2 -12 3 OMIT -2 -12 4 OMIT 4 10 0 OMIT -2 -12 2 OMIT -2 -12 5 OMIT -3 -10 9 OMIT -3 -11 7 OMIT -4 -10 1 TEMP -173.000 SIZE 0.10 0.12 0.12 REM colourless prismatic L.S. 10 ACTA CONF WPDB -2 BOND $H LIST 4 FMAP 2 PLAN 10 WGHT 0.066300 0.563400 FVAR 1.09756 0.69852 C1 1 0.191677 0.294753 0.856344 11.00000 0.02732 0.01545 = 0.02090 -0.00035 0.00492 0.00228 C2 1 0.342003 0.318541 0.789659 11.00000 0.02305 0.01555 = 0.02068 -0.00076 0.00083 0.00219 AFIX 23 H2A 2 0.318105 0.244507 0.744096 11.00000 -1.20000 H2B 2 0.472809 0.322960 0.818099 11.00000 -1.20000 AFIX 0 C3 1 0.331565 0.447212 0.748652 11.00000 0.02423 0.01503 = 0.02248 0.00032 0.00258 0.00188 C4 1 0.126205 0.443247 0.707165 11.00000 0.02520 0.02047 = 0.02969 0.00523 0.00384 0.00509 AFIX 23 H4A 2 0.095394 0.371526 0.660076 11.00000 -1.20000 H4B 2 0.119043 0.526251 0.682403 11.00000 -1.20000 AFIX 0 C5 1 -0.021827 0.422227 0.774248 11.00000 0.02642 0.02460 = 0.03796 0.00770 0.00831 0.00953 AFIX 13 H5 2 -0.154077 0.418678 0.745903 11.00000 -1.20000 AFIX 0 C6 1 -0.012444 0.294017 0.813376 11.00000 0.02546 0.02154 = 0.02900 0.00421 0.00718 0.00452 AFIX 23 H6A 2 -0.046160 0.220122 0.767866 11.00000 -1.20000 H6B 2 -0.107461 0.281865 0.856583 11.00000 -1.20000 AFIX 0 C7 1 0.236062 0.410532 0.926748 11.00000 0.04075 0.01767 = 0.02400 -0.00245 0.00803 0.00265 AFIX 23 H7A 2 0.142721 0.397733 0.970612 11.00000 -1.20000 H7B 2 0.366851 0.414826 0.955172 11.00000 -1.20000 AFIX 0 C8 1 0.223862 0.538578 0.887998 11.00000 0.04801 0.01660 = 0.02906 -0.00343 0.01224 0.00579 AFIX 13 H8 2 0.253665 0.612329 0.934715 11.00000 -1.20000 AFIX 0 C9 1 0.372296 0.560106 0.821169 11.00000 0.03610 0.01407 = 0.02693 -0.00176 0.00535 0.00148 AFIX 23 H9A 2 0.365833 0.643515 0.796826 11.00000 -1.20000 H9B 2 0.503636 0.565452 0.849279 11.00000 -1.20000 AFIX 0 C10 1 0.021530 0.535265 0.845315 11.00000 0.04388 0.02228 = 0.04294 0.00613 0.01933 0.01328 AFIX 23 H10A 2 -0.074271 0.523147 0.888187 11.00000 -1.20000 H10B 2 0.014471 0.618546 0.820901 11.00000 -1.20000 AFIX 0 C11 1 0.201369 0.165103 0.893341 11.00000 0.02308 0.01716 = 0.02297 -0.00116 0.00375 0.00144 C12 1 0.152281 0.043574 0.842655 11.00000 0.02258 0.01920 = 0.02223 -0.00072 0.00159 0.00145 C13 1 0.160466 -0.073512 0.877779 11.00000 0.02912 0.01651 = 0.02807 -0.00134 0.00015 -0.00023 AFIX 43 H13 2 0.124865 -0.153559 0.842158 11.00000 -1.20000 AFIX 0 C14 1 0.219469 -0.075193 0.963523 11.00000 0.02633 0.01932 = 0.03067 0.00478 0.00157 0.00153 AFIX 43 H14 2 0.226537 -0.154787 0.987327 11.00000 -1.20000 AFIX 0 C15 1 0.267448 0.042768 1.012910 11.00000 0.02302 0.02297 = 0.02243 0.00358 0.00128 0.00038 C16 1 0.259306 0.160290 0.979339 11.00000 0.02429 0.01875 = 0.02367 -0.00080 0.00250 -0.00015 AFIX 43 H16 2 0.294164 0.239374 1.016004 11.00000 -1.20000 AFIX 0 C17 1 0.476432 0.467168 0.680624 11.00000 0.02114 0.01710 = 0.02172 0.00168 0.00021 0.00309 C18 1 0.476423 0.373471 0.609807 11.00000 0.02300 0.01728 = 0.02415 0.00132 -0.00050 0.00157 C19 1 0.613973 0.390817 0.549769 11.00000 0.02769 0.02310 = 0.02477 -0.00171 0.00267 0.00456 AFIX 43 H19 2 0.612844 0.324572 0.504150 11.00000 -1.20000 AFIX 0 C20 1 0.750071 0.502416 0.556239 11.00000 0.02445 0.02914 = 0.02623 0.00467 0.00421 0.00478 AFIX 43 H20 2 0.842903 0.514841 0.515547 11.00000 -1.20000 AFIX 0 C21 1 0.747839 0.596025 0.623717 11.00000 0.02157 0.01806 = 0.02670 0.00591 -0.00006 -0.00113 C22 1 0.615250 0.579531 0.685089 11.00000 0.02579 0.01707 = 0.02293 0.00150 -0.00171 0.00213 AFIX 43 H22 2 0.619766 0.646208 0.730778 11.00000 -1.20000 AFIX 0 N1 3 0.329410 0.044199 1.103878 11.00000 0.02755 0.02866 = 0.02479 0.00385 -0.00032 -0.00131 N2 3 0.893089 0.713244 0.633211 11.00000 0.02601 0.02382 = 0.03050 0.00625 -0.00189 -0.00171 O1 4 0.096485 0.042441 0.758072 11.00000 0.03563 0.01714 = 0.02201 -0.00156 -0.00297 -0.00022 H1 2 0.048943 -0.039684 0.737779 11.00000 -1.50000 O2 4 0.350186 -0.058865 1.131712 11.00000 0.04497 0.03105 = 0.03265 0.01210 -0.00534 -0.00161 O3 4 0.358746 0.149556 1.148658 11.00000 0.06124 0.03338 = 0.02538 -0.00244 -0.00664 0.00232 O4 4 0.338128 0.265560 0.600048 11.00000 0.02930 0.01934 = 0.02564 -0.00480 0.00285 -0.00286 H4 2 0.354363 0.219302 0.552981 11.00000 -1.50000 O5 4 1.015460 0.725829 0.581193 11.00000 0.03373 0.03862 = 0.04677 0.00816 0.01406 -0.00609 O6 4 0.889598 0.795726 0.694284 11.00000 0.04001 0.02669 = 0.03503 -0.00147 0.00088 -0.01079 PART 1 C23 1 0.398116 0.037731 0.397261 21.00000 0.02842 0.02355 = 0.01975 -0.00359 -0.00510 0.00308 C24 1 0.560023 0.064272 0.341066 21.00000 0.03232 0.07140 = 0.02725 0.00262 0.00184 -0.00480 AFIX 137 H24A 2 0.508406 0.079078 0.283915 21.00000 -1.50000 H24B 2 0.626247 -0.010793 0.336321 21.00000 -1.50000 H24C 2 0.651241 0.141879 0.366233 21.00000 -1.50000 AFIX 0 C25 1 0.126249 -0.111558 0.422637 21.00000 0.07661 0.06979 = 0.03478 0.00626 -0.00112 -0.03398 AFIX 137 H25A 2 0.020978 -0.067057 0.404763 21.00000 -1.50000 H25B 2 0.165847 -0.086285 0.483721 21.00000 -1.50000 H25C 2 0.082394 -0.206129 0.413010 21.00000 -1.50000 AFIX 0 O7 4 0.379309 0.107177 0.460237 21.00000 0.03824 0.03585 = 0.03148 -0.01134 -0.00363 0.00980 O8 4 0.284578 -0.075711 0.374092 21.00000 0.04946 0.03035 = 0.03324 -0.00892 -0.00270 -0.00981 PART 2 SIMU 0.005 c23b > o8b C23B 1 0.298116 0.003023 0.418656 -21.00000 0.03836 0.03349 = 0.03493 0.00073 -0.00962 0.00610 C24B 1 0.116062 -0.078668 0.437951 -21.00000 0.03221 0.04692 = 0.04289 -0.00578 -0.00503 -0.02113 AFIX 137 H24D 2 0.065036 -0.141268 0.388099 -21.00000 -1.50000 H24E 2 0.021657 -0.022726 0.450983 -21.00000 -1.50000 H24F 2 0.141457 -0.125872 0.487492 -21.00000 -1.50000 AFIX 0 C25B 1 0.537627 0.040196 0.330758 -21.00000 0.03449 0.07190 = 0.04667 -0.00331 -0.00527 0.01884 AFIX 137 H25D 2 0.578154 0.003984 0.276722 -21.00000 -1.50000 H25E 2 0.641587 0.046344 0.376464 -21.00000 -1.50000 H25F 2 0.508284 0.127259 0.324254 -21.00000 -1.50000 AFIX 0 O7B 4 0.337070 0.110571 0.454112 -21.00000 0.03336 0.02864 = 0.03272 -0.01021 -0.00510 0.01200 O8B 4 0.376218 -0.039702 0.351553 -21.00000 0.04685 0.04922 = 0.04410 -0.01141 -0.01032 0.01453 PART 0 HKLF 4 REM P-1_a.res in P-1 REM wR2 = 0.1389, GooF = S = 1.131, Restrained GooF = 1.134 for all data REM R1 = 0.0462 for 3956 Fo > 4sig(Fo) and 0.0501 for all 4426 data REM 372 parameters refined using 24 restraints END WGHT 0.0663 0.5634 REM Highest difference peak 0.280, deepest hole -0.221, 1-sigma level 0.050 Q1 1 0.2006 -0.0201 1.0012 11.00000 0.05 0.28 Q2 1 0.2055 0.3481 0.8978 11.00000 0.05 0.26 Q3 1 0.2871 -0.0594 1.0361 11.00000 0.05 0.25 Q4 1 0.0290 0.4847 0.8050 11.00000 0.05 0.25 Q5 1 -0.0231 0.3580 0.7946 11.00000 0.05 0.25 Q6 1 0.4183 0.4580 0.7126 11.00000 0.05 0.24 Q7 1 0.7277 0.5684 0.5784 11.00000 0.05 0.23 Q8 1 0.1997 0.2363 0.8779 11.00000 0.05 0.23 Q9 1 0.2652 0.3034 0.8245 11.00000 0.05 0.23 Q10 1 0.0672 0.4352 0.7449 11.00000 0.05 0.22 ; _shelx_res_checksum 14107 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 0.1917(2) 0.29475(14) 0.85634(9) 0.0214(3) Uani 1 1 d . . . . . C2 C 0.3420(2) 0.31854(14) 0.78966(9) 0.0201(3) Uani 1 1 d . . . . . H2A H 0.318105 0.244507 0.744096 0.024 Uiso 1 1 calc R U . . . H2B H 0.472809 0.322960 0.818099 0.024 Uiso 1 1 calc R U . . . C3 C 0.3316(2) 0.44721(14) 0.74865(9) 0.0208(3) Uani 1 1 d . . . . . C4 C 0.1262(2) 0.44325(15) 0.70717(10) 0.0248(3) Uani 1 1 d . . . . . H4A H 0.095394 0.371526 0.660076 0.030 Uiso 1 1 calc R U . . . H4B H 0.119043 0.526251 0.682403 0.030 Uiso 1 1 calc R U . . . C5 C -0.0218(2) 0.42223(16) 0.77425(11) 0.0285(4) Uani 1 1 d . . . . . H5 H -0.154077 0.418678 0.745903 0.034 Uiso 1 1 calc R U . . . C6 C -0.0124(2) 0.29402(15) 0.81338(10) 0.0250(3) Uani 1 1 d . . . . . H6A H -0.046160 0.220122 0.767866 0.030 Uiso 1 1 calc R U . . . H6B H -0.107461 0.281865 0.856583 0.030 Uiso 1 1 calc R U . . . C7 C 0.2361(3) 0.41053(15) 0.92675(10) 0.0278(4) Uani 1 1 d . . . . . H7A H 0.142721 0.397733 0.970612 0.033 Uiso 1 1 calc R U . . . H7B H 0.366851 0.414826 0.955172 0.033 Uiso 1 1 calc R U . . . C8 C 0.2239(3) 0.53858(16) 0.88800(11) 0.0311(4) Uani 1 1 d . . . . . H8 H 0.253665 0.612329 0.934715 0.037 Uiso 1 1 calc R U . . . C9 C 0.3723(2) 0.56011(15) 0.82117(10) 0.0262(3) Uani 1 1 d . . . . . H9A H 0.365833 0.643515 0.796826 0.031 Uiso 1 1 calc R U . . . H9B H 0.503636 0.565452 0.849279 0.031 Uiso 1 1 calc R U . . . C10 C 0.0215(3) 0.53527(17) 0.84531(12) 0.0346(4) Uani 1 1 d . . . . . H10A H -0.074271 0.523147 0.888187 0.041 Uiso 1 1 calc R U . . . H10B H 0.014471 0.618546 0.820901 0.041 Uiso 1 1 calc R U . . . C11 C 0.2014(2) 0.16510(14) 0.89334(9) 0.0214(3) Uani 1 1 d . . . . . C12 C 0.1523(2) 0.04357(15) 0.84266(10) 0.0218(3) Uani 1 1 d . . . . . C13 C 0.1605(2) -0.07351(15) 0.87778(10) 0.0254(3) Uani 1 1 d . . . . . H13 H 0.124865 -0.153559 0.842158 0.030 Uiso 1 1 calc R U . . . C14 C 0.2195(2) -0.07519(15) 0.96352(11) 0.0256(3) Uani 1 1 d . . . . . H14 H 0.226537 -0.154787 0.987327 0.031 Uiso 1 1 calc R U . . . C15 C 0.2674(2) 0.04277(15) 1.01291(9) 0.0232(3) Uani 1 1 d . . . . . C16 C 0.2593(2) 0.16029(15) 0.97934(10) 0.0229(3) Uani 1 1 d . . . . . H16 H 0.294164 0.239374 1.016004 0.027 Uiso 1 1 calc R U . . . C17 C 0.4764(2) 0.46717(14) 0.68062(9) 0.0201(3) Uani 1 1 d . . . . . C18 C 0.4764(2) 0.37347(15) 0.60981(10) 0.0219(3) Uani 1 1 d . . . . . C19 C 0.6140(2) 0.39082(16) 0.54977(10) 0.0254(3) Uani 1 1 d . . . . . H19 H 0.612844 0.324572 0.504150 0.031 Uiso 1 1 calc R U . . . C20 C 0.7501(2) 0.50242(16) 0.55624(10) 0.0264(3) Uani 1 1 d . . . . . H20 H 0.842903 0.514841 0.515547 0.032 Uiso 1 1 calc R U . . . C21 C 0.7478(2) 0.59602(15) 0.62372(10) 0.0225(3) Uani 1 1 d . . . . . C22 C 0.6153(2) 0.57953(15) 0.68509(10) 0.0223(3) Uani 1 1 d . . . . . H22 H 0.619766 0.646208 0.730778 0.027 Uiso 1 1 calc R U . . . N1 N 0.3294(2) 0.04420(14) 1.10388(9) 0.0278(3) Uani 1 1 d . . . . . N2 N 0.8931(2) 0.71324(14) 0.63321(9) 0.0275(3) Uani 1 1 d . . . . . O1 O 0.09648(17) 0.04244(11) 0.75807(7) 0.0260(3) Uani 1 1 d . . . . . H1 H 0.049(3) -0.040(2) 0.7378(14) 0.039 Uiso 1 1 d . U . . . O2 O 0.35019(19) -0.05886(13) 1.13171(8) 0.0371(3) Uani 1 1 d . . . . . O3 O 0.3587(2) 0.14956(13) 1.14866(8) 0.0416(3) Uani 1 1 d . . . . . O4 O 0.33813(16) 0.26556(11) 0.60005(7) 0.0260(3) Uani 1 1 d . . . . . H4 H 0.354(3) 0.219(2) 0.5530(15) 0.039 Uiso 1 1 d . U . . . O5 O 1.01546(19) 0.72583(13) 0.58119(9) 0.0404(3) Uani 1 1 d . . . . . O6 O 0.88960(19) 0.79573(12) 0.69428(8) 0.0363(3) Uani 1 1 d . . . . . C23 C 0.3981(5) 0.0377(3) 0.39726(16) 0.0248(9) Uani 0.699(9) 1 d . . P A 1 C24 C 0.5600(14) 0.0643(9) 0.3411(5) 0.0455(18) Uani 0.699(9) 1 d . . P A 1 H24A H 0.508406 0.079078 0.283915 0.068 Uiso 0.699(9) 1 calc R U P A 1 H24B H 0.626247 -0.010793 0.336321 0.068 Uiso 0.699(9) 1 calc R U P A 1 H24C H 0.651241 0.141879 0.366233 0.068 Uiso 0.699(9) 1 calc R U P A 1 C25 C 0.1262(15) -0.1116(9) 0.4226(5) 0.066(2) Uani 0.699(9) 1 d . . P A 1 H25A H 0.020978 -0.067057 0.404763 0.099 Uiso 0.699(9) 1 calc R U P A 1 H25B H 0.165847 -0.086285 0.483721 0.099 Uiso 0.699(9) 1 calc R U P A 1 H25C H 0.082394 -0.206129 0.413010 0.099 Uiso 0.699(9) 1 calc R U P A 1 O7 O 0.3793(13) 0.1072(13) 0.4602(9) 0.0360(14) Uani 0.699(9) 1 d . . P A 1 O8 O 0.2846(5) -0.0757(2) 0.37409(16) 0.0407(8) Uani 0.699(9) 1 d . . P A 1 C23B C 0.2981(15) 0.0030(8) 0.4187(5) 0.036(2) Uani 0.301(9) 1 d . U P A 2 C24B C 0.116(2) -0.0787(18) 0.4380(13) 0.045(3) Uani 0.301(9) 1 d . U P A 2 H24D H 0.065036 -0.141268 0.388099 0.068 Uiso 0.301(9) 1 calc R U P A 2 H24E H 0.021657 -0.022726 0.450983 0.068 Uiso 0.301(9) 1 calc R U P A 2 H24F H 0.141457 -0.125872 0.487492 0.068 Uiso 0.301(9) 1 calc R U P A 2 C25B C 0.538(3) 0.040(2) 0.3308(15) 0.051(4) Uani 0.301(9) 1 d . U P A 2 H25D H 0.578154 0.003984 0.276722 0.076 Uiso 0.301(9) 1 calc R U P A 2 H25E H 0.641587 0.046344 0.376464 0.076 Uiso 0.301(9) 1 calc R U P A 2 H25F H 0.508284 0.127259 0.324254 0.076 Uiso 0.301(9) 1 calc R U P A 2 O7B O 0.337(3) 0.111(3) 0.454(2) 0.032(3) Uani 0.301(9) 1 d . U P A 2 O8B O 0.3762(13) -0.0397(8) 0.3516(5) 0.048(2) Uani 0.301(9) 1 d . U P A 2 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 0.0273(8) 0.0154(7) 0.0209(7) -0.0003(5) 0.0049(6) 0.0023(6) C2 0.0230(7) 0.0156(7) 0.0207(7) -0.0008(5) 0.0008(5) 0.0022(5) C3 0.0242(7) 0.0150(7) 0.0225(7) 0.0003(5) 0.0026(6) 0.0019(5) C4 0.0252(8) 0.0205(8) 0.0297(8) 0.0052(6) 0.0038(6) 0.0051(6) C5 0.0264(8) 0.0246(8) 0.0380(9) 0.0077(7) 0.0083(7) 0.0095(6) C6 0.0255(8) 0.0215(8) 0.0290(8) 0.0042(6) 0.0072(6) 0.0045(6) C7 0.0408(9) 0.0177(8) 0.0240(7) -0.0025(6) 0.0080(6) 0.0027(6) C8 0.0480(10) 0.0166(8) 0.0291(8) -0.0034(6) 0.0122(7) 0.0058(7) C9 0.0361(9) 0.0141(7) 0.0269(8) -0.0018(6) 0.0054(6) 0.0015(6) C10 0.0439(10) 0.0223(9) 0.0429(10) 0.0061(7) 0.0193(8) 0.0133(7) C11 0.0231(7) 0.0172(7) 0.0230(7) -0.0012(6) 0.0038(6) 0.0014(5) C12 0.0226(7) 0.0192(8) 0.0222(7) -0.0007(6) 0.0016(5) 0.0015(6) C13 0.0291(8) 0.0165(7) 0.0281(8) -0.0013(6) 0.0002(6) -0.0002(6) C14 0.0263(8) 0.0193(8) 0.0307(8) 0.0048(6) 0.0016(6) 0.0015(6) C15 0.0230(7) 0.0230(8) 0.0224(7) 0.0036(6) 0.0013(6) 0.0004(6) C16 0.0243(7) 0.0188(7) 0.0237(7) -0.0008(6) 0.0025(6) -0.0002(6) C17 0.0211(7) 0.0171(7) 0.0217(7) 0.0017(5) 0.0002(5) 0.0031(5) C18 0.0230(7) 0.0173(7) 0.0242(7) 0.0013(5) -0.0005(6) 0.0016(5) C19 0.0277(8) 0.0231(8) 0.0248(7) -0.0017(6) 0.0027(6) 0.0046(6) C20 0.0245(8) 0.0291(9) 0.0262(8) 0.0047(6) 0.0042(6) 0.0048(6) C21 0.0216(7) 0.0181(7) 0.0267(7) 0.0059(6) -0.0001(6) -0.0011(6) C22 0.0258(7) 0.0171(7) 0.0229(7) 0.0015(5) -0.0017(6) 0.0021(6) N1 0.0276(7) 0.0287(8) 0.0248(7) 0.0039(5) -0.0003(5) -0.0013(5) N2 0.0260(7) 0.0238(7) 0.0305(7) 0.0063(5) -0.0019(5) -0.0017(5) O1 0.0356(6) 0.0171(6) 0.0220(5) -0.0016(4) -0.0030(4) -0.0002(4) O2 0.0450(7) 0.0310(7) 0.0326(6) 0.0121(5) -0.0053(5) -0.0016(5) O3 0.0612(9) 0.0334(7) 0.0254(6) -0.0024(5) -0.0066(6) 0.0023(6) O4 0.0293(6) 0.0193(6) 0.0256(6) -0.0048(4) 0.0029(4) -0.0029(4) O5 0.0337(7) 0.0386(8) 0.0468(8) 0.0082(6) 0.0141(6) -0.0061(5) O6 0.0400(7) 0.0267(7) 0.0350(7) -0.0015(5) 0.0009(5) -0.0108(5) C23 0.0284(17) 0.0236(15) 0.0198(12) -0.0036(10) -0.0051(10) 0.0031(12) C24 0.032(3) 0.071(4) 0.027(2) 0.003(2) 0.0018(19) -0.005(2) C25 0.077(4) 0.070(5) 0.035(3) 0.006(3) -0.001(2) -0.034(4) O7 0.038(4) 0.0358(19) 0.031(2) -0.0113(14) -0.004(3) 0.010(3) O8 0.0495(17) 0.0304(14) 0.0332(12) -0.0089(9) -0.0027(11) -0.0098(11) C23B 0.038(4) 0.033(3) 0.035(3) 0.001(3) -0.010(3) 0.006(3) C24B 0.032(4) 0.047(6) 0.043(7) -0.006(4) -0.005(4) -0.021(4) C25B 0.034(6) 0.072(8) 0.047(7) -0.003(5) -0.005(5) 0.019(6) O7B 0.033(7) 0.029(3) 0.033(4) -0.010(3) -0.005(5) 0.012(5) O8B 0.047(4) 0.049(4) 0.044(3) -0.011(3) -0.010(3) 0.015(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 C7 111.57(12) . . ? C11 C1 C6 110.49(12) . . ? C7 C1 C6 107.32(12) . . ? C11 C1 C2 109.96(12) . . ? C7 C1 C2 107.71(12) . . ? C6 C1 C2 109.71(12) . . ? C1 C2 C3 111.32(11) . . ? 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 . . ? C17 C3 C9 111.34(12) . . ? C17 C3 C4 109.66(12) . . ? C9 C3 C4 107.47(12) . . ? C17 C3 C2 110.74(11) . . ? C9 C3 C2 107.85(12) . . ? C4 C3 C2 109.70(12) . . ? C3 C4 C5 110.52(13) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C10 C5 C6 109.27(14) . . ? C10 C5 C4 109.55(14) . . ? C6 C5 C4 110.23(12) . . ? C10 C5 H5 109.3 . . ? C6 C5 H5 109.3 . . ? C4 C5 H5 109.3 . . ? C5 C6 C1 110.77(13) . . ? C5 C6 H6A 109.5 . . ? C1 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 108.1 . . ? C8 C7 C1 110.39(13) . . ? C8 C7 H7A 109.6 . . ? C1 C7 H7A 109.6 . . ? C8 C7 H7B 109.6 . . ? C1 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C10 C8 C7 110.49(15) . . ? C10 C8 C9 109.63(14) . . ? C7 C8 C9 109.61(13) . . ? C10 C8 H8 109.0 . . ? C7 C8 H8 109.0 . . ? C9 C8 H8 109.0 . . ? C3 C9 C8 110.33(13) . . ? C3 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 . . ? C3 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C5 C10 C8 108.39(13) . . ? C5 C10 H10A 110.0 . . ? C8 C10 H10A 110.0 . . ? C5 C10 H10B 110.0 . . ? C8 C10 H10B 110.0 . . ? H10A C10 H10B 108.4 . . ? C16 C11 C12 115.98(14) . . ? C16 C11 C1 121.65(13) . . ? C12 C11 C1 122.37(13) . . ? O1 C12 C13 119.99(13) . . ? O1 C12 C11 118.55(13) . . ? C13 C12 C11 121.47(14) . . ? C14 C13 C12 121.24(14) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 117.42(14) . . ? C15 C14 H14 121.3 . . ? C13 C14 H14 121.3 . . ? C14 C15 C16 122.25(14) . . ? C14 C15 N1 118.73(14) . . ? C16 C15 N1 119.02(14) . . ? C15 C16 C11 121.64(14) . . ? C15 C16 H16 119.2 . . ? C11 C16 H16 119.2 . . ? C22 C17 C18 116.10(14) . . ? C22 C17 C3 121.56(13) . . ? C18 C17 C3 122.34(13) . . ? O4 C18 C19 119.81(13) . . ? O4 C18 C17 118.44(13) . . ? C19 C18 C17 121.75(14) . . ? C20 C19 C18 120.74(14) . . ? C20 C19 H19 119.6 . . ? C18 C19 H19 119.6 . . ? C19 C20 C21 117.92(14) . . ? C19 C20 H20 121.0 . . ? C21 C20 H20 121.0 . . ? C20 C21 C22 122.27(14) . . ? C20 C21 N2 118.97(14) . . ? C22 C21 N2 118.71(14) . . ? C17 C22 C21 121.17(14) . . ? C17 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? O2 N1 O3 123.30(14) . . ? O2 N1 C15 118.69(13) . . ? O3 N1 C15 118.01(14) . . ? O5 N2 O6 122.90(14) . . ? O5 N2 C21 118.98(14) . . ? O6 N2 C21 118.11(14) . . ? C12 O1 H1 107.6(15) . . ? C18 O4 H4 107.6(15) . . ? O7 C23 O8 122.8(8) . . ? O7 C23 C24 124.2(7) . . ? O8 C23 C24 112.7(4) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O8 C25 H25A 109.5 . . ? O8 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O8 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 O8 C25 117.8(5) . . ? O7B C23B O8B 125.3(18) . . ? O7B C23B C24B 117.1(16) . . ? O8B C23B C24B 115.8(10) . . ? C23B C24B H24D 109.5 . . ? C23B C24B H24E 109.5 . . ? H24D C24B H24E 109.5 . . ? C23B C24B H24F 109.5 . . ? H24D C24B H24F 109.5 . . ? H24E C24B H24F 109.5 . . ? O8B C25B H25D 109.5 . . ? O8B C25B H25E 109.5 . . ? H25D C25B H25E 109.5 . . ? O8B C25B H25F 109.5 . . ? H25D C25B H25F 109.5 . . ? H25E C25B H25F 109.5 . . ? C23B O8B C25B 115.6(13) . . ? 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 1.532(2) . ? C1 C7 1.540(2) . ? C1 C6 1.548(2) . ? C1 C2 1.551(2) . ? C2 C3 1.554(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C17 1.536(2) . ? C3 C9 1.541(2) . ? C3 C4 1.541(2) . ? C4 C5 1.541(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.527(2) . ? C5 C6 1.534(2) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.533(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.530(3) . ? C8 C9 1.541(2) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.391(2) . ? C11 C12 1.415(2) . ? C12 O1 1.3572(18) . ? C12 C13 1.396(2) . ? C13 C14 1.384(2) . ? C13 H13 0.9500 . ? C14 C15 1.375(2) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 N1 1.4625(19) . ? C16 H16 0.9500 . ? C17 C22 1.391(2) . ? C17 C18 1.416(2) . ? C18 O4 1.3521(19) . ? C18 C19 1.404(2) . ? C19 C20 1.373(2) . ? C19 H19 0.9500 . ? C20 C21 1.380(2) . ? C20 H20 0.9500 . ? C21 C22 1.394(2) . ? C21 N2 1.449(2) . ? C22 H22 0.9500 . ? N1 O2 1.2262(19) . ? N1 O3 1.2312(19) . ? N2 O5 1.2312(19) . ? N2 O6 1.2363(19) . ? O1 H1 0.89(2) . ? O4 H4 0.87(2) . ? C23 O7 1.203(14) . ? C23 O8 1.321(5) . ? C23 C24 1.499(10) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O8 1.417(11) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C23B O7B 1.19(3) . ? C23B O8B 1.303(15) . ? C23B C24B 1.49(2) . ? C24B H24D 0.9800 . ? C24B H24E 0.9800 . ? C24B H24F 0.9800 . ? C25B O8B 1.37(3) . ? C25B H25D 0.9800 . ? C25B H25E 0.9800 . ? C25B H25F 0.9800 . ? 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 178.17(11) . . . . ? C7 C1 C2 C3 -60.06(15) . . . . ? C6 C1 C2 C3 56.46(15) . . . . ? C1 C2 C3 C17 -178.10(11) . . . . ? C1 C2 C3 C9 59.85(15) . . . . ? C1 C2 C3 C4 -56.92(15) . . . . ? C17 C3 C4 C5 179.57(12) . . . . ? C9 C3 C4 C5 -59.26(16) . . . . ? C2 C3 C4 C5 57.75(16) . . . . ? C3 C4 C5 C10 61.14(16) . . . . ? C3 C4 C5 C6 -59.13(17) . . . . ? C10 C5 C6 C1 -61.65(16) . . . . ? C4 C5 C6 C1 58.79(17) . . . . ? C11 C1 C6 C5 -178.60(12) . . . . ? C7 C1 C6 C5 59.55(16) . . . . ? C2 C1 C6 C5 -57.21(16) . . . . ? C11 C1 C7 C8 -179.59(13) . . . . ? C6 C1 C7 C8 -58.42(17) . . . . ? C2 C1 C7 C8 59.65(17) . . . . ? C1 C7 C8 C10 60.42(17) . . . . ? C1 C7 C8 C9 -60.50(18) . . . . ? C17 C3 C9 C8 179.38(12) . . . . ? C4 C3 C9 C8 59.27(16) . . . . ? C2 C3 C9 C8 -58.94(16) . . . . ? C10 C8 C9 C3 -61.29(16) . . . . ? C7 C8 C9 C3 60.15(18) . . . . ? C6 C5 C10 C8 60.29(17) . . . . ? C4 C5 C10 C8 -60.56(17) . . . . ? C7 C8 C10 C5 -60.16(17) . . . . ? C9 C8 C10 C5 60.75(17) . . . . ? C7 C1 C11 C16 -4.8(2) . . . . ? C6 C1 C11 C16 -124.08(15) . . . . ? C2 C1 C11 C16 114.68(15) . . . . ? C7 C1 C11 C12 175.20(14) . . . . ? C6 C1 C11 C12 55.89(18) . . . . ? C2 C1 C11 C12 -65.35(18) . . . . ? C16 C11 C12 O1 -179.38(13) . . . . ? C1 C11 C12 O1 0.7(2) . . . . ? C16 C11 C12 C13 0.5(2) . . . . ? C1 C11 C12 C13 -179.43(14) . . . . ? O1 C12 C13 C14 179.07(14) . . . . ? C11 C12 C13 C14 -0.9(2) . . . . ? C12 C13 C14 C15 0.8(2) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C13 C14 C15 N1 179.69(14) . . . . ? C14 C15 C16 C11 0.1(2) . . . . ? N1 C15 C16 C11 -179.96(14) . . . . ? C12 C11 C16 C15 -0.2(2) . . . . ? C1 C11 C16 C15 179.78(14) . . . . ? C9 C3 C17 C22 -3.87(19) . . . . ? C4 C3 C17 C22 114.93(15) . . . . ? C2 C3 C17 C22 -123.86(14) . . . . ? C9 C3 C17 C18 176.46(13) . . . . ? C4 C3 C17 C18 -64.73(17) . . . . ? C2 C3 C17 C18 56.47(17) . . . . ? C22 C17 C18 O4 -176.63(13) . . . . ? C3 C17 C18 O4 3.0(2) . . . . ? C22 C17 C18 C19 2.6(2) . . . . ? C3 C17 C18 C19 -177.68(13) . . . . ? O4 C18 C19 C20 176.95(14) . . . . ? C17 C18 C19 C20 -2.3(2) . . . . ? C18 C19 C20 C21 0.4(2) . . . . ? C19 C20 C21 C22 1.0(2) . . . . ? C19 C20 C21 N2 178.44(14) . . . . ? C18 C17 C22 C21 -1.2(2) . . . . ? C3 C17 C22 C21 179.10(13) . . . . ? C20 C21 C22 C17 -0.6(2) . . . . ? N2 C21 C22 C17 -178.02(13) . . . . ? C14 C15 N1 O2 5.3(2) . . . . ? C16 C15 N1 O2 -174.60(14) . . . . ? C14 C15 N1 O3 -174.93(15) . . . . ? C16 C15 N1 O3 5.2(2) . . . . ? C20 C21 N2 O5 -0.5(2) . . . . ? C22 C21 N2 O5 177.01(14) . . . . ? C20 C21 N2 O6 -179.60(14) . . . . ? C22 C21 N2 O6 -2.1(2) . . . . ? O7 C23 O8 C25 4.6(8) . . . . ? C24 C23 O8 C25 179.9(7) . . . . ? O7B C23B O8B C25B 11.8(19) . . . . ? C24B C23B O8B C25B 176.0(15) . . . . ?