#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:53:54 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247591.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_7247591 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 O7' _chemical_formula_weight 468.49 _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 95.066(4) _cell_angle_beta 92.516(4) _cell_angle_gamma 100.761(3) _cell_formula_units_Z 2 _cell_length_a 6.9004(7) _cell_length_b 10.5029(11) _cell_length_c 15.8453(17) _cell_measurement_reflns_used 9913 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 79.29 _cell_measurement_theta_min 4.31 _cell_volume 1121.6(2) _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 0.957 _diffrn_measured_fraction_theta_max 0.904 _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 0.0300 _diffrn_reflns_av_unetI/netI 0.0249 _diffrn_reflns_Laue_measured_fraction_full 0.957 _diffrn_reflns_Laue_measured_fraction_max 0.904 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 16169 _diffrn_reflns_point_group_measured_fraction_full 0.957 _diffrn_reflns_point_group_measured_fraction_max 0.904 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 80.080 _diffrn_reflns_theta_min 2.805 _diffrn_source 'rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 0.845 _exptl_absorpt_correction_T_max 0.9424 _exptl_absorpt_correction_T_min 0.8532 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.387 _exptl_crystal_description plate _exptl_crystal_F_000 496 _exptl_crystal_size_max 0.100 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.323 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 315 _refine_ls_number_reflns 4439 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0414 _refine_ls_R_factor_gt 0.0375 _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^)+(0.0577P)^2^+0.3598P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1040 _refine_ls_wR_factor_ref 0.1075 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3983 _reflns_number_total 4439 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00775h2.cif _cod_data_source_block 1a _cod_depositor_comments 'Adding full bibliography for 7247591--7247596.cif.' _cod_database_code 7247591 _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 0.920 _shelx_estimated_absorpt_t_max 0.959 _shelx_res_file ; TITL P-1_a.res in P-1 P-1_a.res created by SHELXL-2018/3 at 13:07:51 on 12-Dec-2022 REM Old TITL P-1 in P-1 REM SHELXT solution in P-1: R1 0.128, Rweak 0.005, Alpha 0.032 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C27 O7 CELL 1.54178 6.9004 10.5029 15.8453 95.066 92.516 100.761 ZERR 2.000 0.0007 0.0011 0.0017 0.004 0.004 0.003 LATT 1 SFAC C H N O UNIT 50 56 4 14 OMIT 5 -6 15 TEMP -173.000 SIZE 0.05 0.10 0.10 REM yellow plate L.S. 10 ACTA CONF WPDB -2 BOND $H LIST 4 FMAP 2 PLAN 20 WGHT 0.057700 0.359800 FVAR 0.95757 C1 1 0.187879 0.298528 0.854515 11.00000 0.02119 0.01307 = 0.02092 0.00149 0.00167 0.00024 C2 1 0.344248 0.326067 0.787748 11.00000 0.01931 0.01352 = 0.01963 0.00118 0.00088 0.00041 AFIX 23 H2A 2 0.478143 0.334802 0.815428 11.00000 -1.20000 H2B 2 0.324447 0.251789 0.743196 11.00000 -1.20000 AFIX 0 C3 1 0.328481 0.452407 0.746467 11.00000 0.01981 0.01272 = 0.02096 0.00113 0.00048 -0.00009 C4 1 0.117080 0.441775 0.706910 11.00000 0.02112 0.01630 = 0.02593 0.00478 0.00077 0.00268 AFIX 23 H4A 2 0.106679 0.523095 0.681349 11.00000 -1.20000 H4B 2 0.088817 0.368961 0.661271 11.00000 -1.20000 AFIX 0 C5 1 -0.035233 0.418439 0.774345 11.00000 0.02047 0.01938 = 0.03296 0.00593 0.00425 0.00405 AFIX 13 H5 2 -0.170896 0.411158 0.747142 11.00000 -1.20000 AFIX 0 C6 1 -0.021394 0.291965 0.813511 11.00000 0.01981 0.01650 = 0.02841 0.00402 0.00334 0.00078 AFIX 23 H6A 2 -0.052572 0.217715 0.768933 11.00000 -1.20000 H6B 2 -0.119584 0.277422 0.857082 11.00000 -1.20000 AFIX 0 C7 1 0.227443 0.414647 0.923672 11.00000 0.03012 0.01552 = 0.02277 0.00018 0.00541 0.00001 AFIX 23 H7A 2 0.130157 0.399580 0.967562 11.00000 -1.20000 H7B 2 0.361177 0.422336 0.951290 11.00000 -1.20000 AFIX 0 C8 1 0.211895 0.541496 0.884739 11.00000 0.03412 0.01381 = 0.02609 -0.00028 0.00760 0.00277 AFIX 13 H8 2 0.239237 0.615572 0.930489 11.00000 -1.20000 AFIX 0 C9 1 0.364715 0.566025 0.817497 11.00000 0.02685 0.01296 = 0.02375 0.00035 0.00308 -0.00006 AFIX 23 H9A 2 0.499404 0.575178 0.844461 11.00000 -1.20000 H9B 2 0.355378 0.648216 0.792841 11.00000 -1.20000 AFIX 0 C10 1 0.004069 0.532277 0.843942 11.00000 0.03104 0.01793 = 0.03554 0.00440 0.01159 0.00723 AFIX 23 H10A 2 -0.094847 0.517929 0.887234 11.00000 -1.20000 H10B 2 -0.006094 0.614351 0.819297 11.00000 -1.20000 AFIX 0 C11 1 0.202473 0.170121 0.890888 11.00000 0.01743 0.01505 = 0.02245 0.00204 0.00269 -0.00086 C12 1 0.162844 0.049253 0.840147 11.00000 0.01785 0.01721 = 0.02005 0.00196 0.00134 -0.00063 C13 1 0.173360 -0.067683 0.874438 11.00000 0.02178 0.01407 = 0.02483 0.00008 0.00009 0.00009 AFIX 43 H13 2 0.145073 -0.147249 0.838729 11.00000 -1.20000 AFIX 0 C14 1 0.224182 -0.068844 0.959271 11.00000 0.02060 0.01618 = 0.02714 0.00484 0.00146 0.00023 AFIX 43 H14 2 0.231253 -0.147984 0.982939 11.00000 -1.20000 AFIX 0 C15 1 0.264647 0.049302 1.008925 11.00000 0.01713 0.02081 = 0.02061 0.00412 0.00067 -0.00088 C16 1 0.253879 0.166098 0.976091 11.00000 0.01991 0.01727 = 0.02174 0.00096 0.00252 -0.00116 AFIX 43 H16 2 0.282249 0.244816 1.012652 11.00000 -1.20000 AFIX 0 C17 1 0.478566 0.474848 0.678393 11.00000 0.01991 0.01443 = 0.02010 0.00357 -0.00115 0.00250 C18 1 0.480184 0.381845 0.608120 11.00000 0.02172 0.01432 = 0.02133 0.00289 -0.00267 0.00123 C19 1 0.621472 0.402080 0.547289 11.00000 0.02447 0.01908 = 0.02092 0.00149 -0.00034 0.00550 AFIX 43 H19 2 0.620861 0.337071 0.501561 11.00000 -1.20000 AFIX 0 C20 1 0.761239 0.515432 0.553234 11.00000 0.02029 0.02286 = 0.02373 0.00607 0.00233 0.00477 AFIX 43 H20 2 0.856335 0.530228 0.511847 11.00000 -1.20000 AFIX 0 C21 1 0.758752 0.607015 0.621352 11.00000 0.01908 0.01579 = 0.02484 0.00581 -0.00197 0.00051 C22 1 0.621099 0.588654 0.682762 11.00000 0.02030 0.01575 = 0.02079 0.00325 -0.00157 0.00260 AFIX 43 H22 2 0.624243 0.654464 0.728238 11.00000 -1.20000 AFIX 0 C23 1 0.352679 0.026682 0.410078 11.00000 0.03932 0.02208 = 0.02340 -0.00038 -0.00738 0.00912 C24 1 0.188406 -0.081285 0.422389 11.00000 0.06864 0.05075 = 0.07368 0.03136 -0.03030 -0.02129 AFIX 137 H24A 2 0.074938 -0.077780 0.383832 11.00000 -1.50000 H24B 2 0.150486 -0.072991 0.481212 11.00000 -1.50000 H24C 2 0.230944 -0.164627 0.410279 11.00000 -1.50000 AFIX 0 C25 1 0.473395 0.012555 0.336134 11.00000 0.08364 0.08009 = 0.03418 0.00225 0.01070 0.04703 AFIX 137 H25A 2 0.388514 0.000730 0.283710 11.00000 -1.50000 H25B 2 0.535916 -0.063394 0.339830 11.00000 -1.50000 H25C 2 0.575700 0.090974 0.335893 11.00000 -1.50000 AFIX 0 N1 3 0.318280 0.050689 1.098977 11.00000 0.02176 0.02250 = 0.02304 0.00489 0.00033 -0.00334 N2 3 0.909639 0.724551 0.630899 11.00000 0.02177 0.01928 = 0.02749 0.00641 0.00038 -0.00079 O1 4 0.114898 0.047748 0.756175 11.00000 0.03077 0.01410 = 0.01987 -0.00020 -0.00195 -0.00046 H1 2 0.075871 -0.032633 0.733623 11.00000 -1.50000 O2 4 0.335546 -0.052794 1.126349 11.00000 0.03627 0.02616 = 0.02767 0.01199 -0.00346 -0.00210 O3 4 0.345436 0.155287 1.143597 11.00000 0.04680 0.02654 = 0.02377 -0.00149 -0.00489 -0.00050 O4 4 0.339462 0.272052 0.599836 11.00000 0.02875 0.01565 = 0.02346 -0.00205 0.00038 -0.00340 H4 2 0.351033 0.223901 0.552357 11.00000 -1.50000 O5 4 1.035200 0.740153 0.578549 11.00000 0.03265 0.03427 = 0.04336 0.00467 0.01593 -0.00733 O6 4 0.906840 0.804721 0.692879 11.00000 0.03347 0.02242 = 0.03179 -0.00175 0.00242 -0.00903 O7 4 0.390261 0.124878 0.458624 11.00000 0.05840 0.03428 = 0.03289 -0.01127 -0.00575 0.01291 HKLF 4 REM P-1_a.res in P-1 REM wR2 = 0.1075, GooF = S = 1.058, Restrained GooF = 1.058 for all data REM R1 = 0.0375 for 3983 Fo > 4sig(Fo) and 0.0414 for all 4439 data REM 315 parameters refined using 0 restraints END WGHT 0.0577 0.3598 REM Highest difference peak 0.323, deepest hole -0.276, 1-sigma level 0.045 Q1 1 0.2927 0.0821 0.4821 11.00000 0.05 0.32 Q2 1 0.2177 0.4803 0.9032 11.00000 0.05 0.24 Q3 1 -0.0233 0.3572 0.7918 11.00000 0.05 0.23 Q4 1 0.1943 -0.1439 0.4657 11.00000 0.05 0.22 Q5 1 0.2014 0.2323 0.8729 11.00000 0.05 0.22 Q6 1 0.2542 0.3126 0.8228 11.00000 0.05 0.20 Q7 1 -0.0037 0.4651 0.8156 11.00000 0.05 0.19 Q8 1 0.6819 0.4622 0.5515 11.00000 0.05 0.18 Q9 1 0.5046 0.4223 0.6573 11.00000 0.05 0.18 Q10 1 0.5403 0.5268 0.6808 11.00000 0.05 0.17 Q11 1 0.1930 0.3547 0.8875 11.00000 0.05 0.17 Q12 1 0.3540 0.5042 0.7802 11.00000 0.05 0.17 Q13 1 0.2606 0.1736 0.9256 11.00000 0.05 0.17 Q14 1 0.5913 0.3811 0.5827 11.00000 0.05 0.17 Q15 1 0.3362 0.3926 0.7684 11.00000 0.05 0.16 Q16 1 0.0450 0.4281 0.7452 11.00000 0.05 0.16 Q17 1 0.1892 0.1138 0.8651 11.00000 0.05 0.16 Q18 1 0.0819 0.2964 0.8319 11.00000 0.05 0.16 Q19 1 0.7366 0.4453 0.5751 11.00000 0.05 0.16 Q20 1 0.7192 0.5783 0.6593 11.00000 0.05 0.16 ; _shelx_res_checksum 31583 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 0.18788(18) 0.29853(11) 0.85452(8) 0.0188(2) Uani 1 1 d . . . . . C2 C 0.34425(17) 0.32607(11) 0.78775(7) 0.0179(2) Uani 1 1 d . . . . . H2A H 0.478143 0.334802 0.815428 0.021 Uiso 1 1 calc R U . . . H2B H 0.324447 0.251789 0.743196 0.021 Uiso 1 1 calc R U . . . C3 C 0.32848(18) 0.45241(11) 0.74647(8) 0.0183(2) Uani 1 1 d . . . . . C4 C 0.11708(18) 0.44177(11) 0.70691(8) 0.0211(3) Uani 1 1 d . . . . . H4A H 0.106679 0.523095 0.681349 0.025 Uiso 1 1 calc R U . . . H4B H 0.088817 0.368961 0.661271 0.025 Uiso 1 1 calc R U . . . C5 C -0.03523(19) 0.41844(12) 0.77434(9) 0.0240(3) Uani 1 1 d . . . . . H5 H -0.170896 0.411158 0.747142 0.029 Uiso 1 1 calc R U . . . C6 C -0.02139(18) 0.29197(11) 0.81351(8) 0.0218(3) Uani 1 1 d . . . . . H6A H -0.052572 0.217715 0.768933 0.026 Uiso 1 1 calc R U . . . H6B H -0.119584 0.277422 0.857082 0.026 Uiso 1 1 calc R U . . . C7 C 0.2274(2) 0.41465(11) 0.92367(8) 0.0234(3) Uani 1 1 d . . . . . H7A H 0.130157 0.399580 0.967562 0.028 Uiso 1 1 calc R U . . . H7B H 0.361177 0.422336 0.951290 0.028 Uiso 1 1 calc R U . . . C8 C 0.2119(2) 0.54150(11) 0.88474(8) 0.0249(3) Uani 1 1 d . . . . . H8 H 0.239237 0.615572 0.930489 0.030 Uiso 1 1 calc R U . . . C9 C 0.36472(19) 0.56602(11) 0.81750(8) 0.0217(3) Uani 1 1 d . . . . . H9A H 0.499404 0.575178 0.844461 0.026 Uiso 1 1 calc R U . . . H9B H 0.355378 0.648216 0.792841 0.026 Uiso 1 1 calc R U . . . C10 C 0.0041(2) 0.53228(12) 0.84394(9) 0.0274(3) Uani 1 1 d . . . . . H10A H -0.094847 0.517929 0.887234 0.033 Uiso 1 1 calc R U . . . H10B H -0.006094 0.614351 0.819297 0.033 Uiso 1 1 calc R U . . . C11 C 0.20247(17) 0.17012(11) 0.89089(8) 0.0188(2) Uani 1 1 d . . . . . C12 C 0.16284(17) 0.04925(11) 0.84015(8) 0.0189(2) Uani 1 1 d . . . . . C13 C 0.17336(18) -0.06768(11) 0.87444(8) 0.0208(3) Uani 1 1 d . . . . . H13 H 0.145073 -0.147249 0.838729 0.025 Uiso 1 1 calc R U . . . C14 C 0.22418(18) -0.06884(11) 0.95927(8) 0.0216(3) Uani 1 1 d . . . . . H14 H 0.231253 -0.147984 0.982939 0.026 Uiso 1 1 calc R U . . . C15 C 0.26465(17) 0.04930(11) 1.00892(8) 0.0200(3) Uani 1 1 d . . . . . C16 C 0.25388(18) 0.16610(11) 0.97609(8) 0.0203(3) Uani 1 1 d . . . . . H16 H 0.282249 0.244816 1.012652 0.024 Uiso 1 1 calc R U . . . C17 C 0.47857(18) 0.47485(11) 0.67839(8) 0.0182(2) Uani 1 1 d . . . . . C18 C 0.48018(18) 0.38184(11) 0.60812(8) 0.0195(2) Uani 1 1 d . . . . . C19 C 0.62147(19) 0.40208(12) 0.54729(8) 0.0214(3) Uani 1 1 d . . . . . H19 H 0.620861 0.337071 0.501561 0.026 Uiso 1 1 calc R U . . . C20 C 0.76124(18) 0.51543(12) 0.55323(8) 0.0220(3) Uani 1 1 d . . . . . H20 H 0.856335 0.530228 0.511847 0.026 Uiso 1 1 calc R U . . . C21 C 0.75875(18) 0.60701(11) 0.62135(8) 0.0201(2) Uani 1 1 d . . . . . C22 C 0.62110(18) 0.58865(11) 0.68276(8) 0.0191(2) Uani 1 1 d . . . . . H22 H 0.624243 0.654464 0.728238 0.023 Uiso 1 1 calc R U . . . C23 C 0.3527(2) 0.02668(13) 0.41008(9) 0.0283(3) Uani 1 1 d . . . . . C24 C 0.1884(3) -0.0813(2) 0.42239(15) 0.0681(7) Uani 1 1 d . . . . . H24A H 0.074938 -0.077780 0.383832 0.102 Uiso 1 1 calc R U . . . H24B H 0.150486 -0.072991 0.481212 0.102 Uiso 1 1 calc R U . . . H24C H 0.230944 -0.164627 0.410279 0.102 Uiso 1 1 calc R U . . . C25 C 0.4734(4) 0.0126(2) 0.33613(12) 0.0619(6) Uani 1 1 d . . . . . H25A H 0.388514 0.000730 0.283710 0.093 Uiso 1 1 calc R U . . . H25B H 0.535916 -0.063394 0.339830 0.093 Uiso 1 1 calc R U . . . H25C H 0.575700 0.090974 0.335893 0.093 Uiso 1 1 calc R U . . . N1 N 0.31828(16) 0.05069(10) 1.09898(7) 0.0233(2) Uani 1 1 d . . . . . N2 N 0.90964(16) 0.72455(10) 0.63090(7) 0.0232(2) Uani 1 1 d . . . . . O1 O 0.11490(13) 0.04775(8) 0.75618(6) 0.0224(2) Uani 1 1 d . . . . . H1 H 0.076(3) -0.0326(18) 0.7336(11) 0.034 Uiso 1 1 d . U . . . O2 O 0.33555(15) -0.05279(9) 1.12635(6) 0.0307(2) Uani 1 1 d . . . . . O3 O 0.34544(16) 0.15529(9) 1.14360(6) 0.0338(2) Uani 1 1 d . . . . . O4 O 0.33946(14) 0.27205(8) 0.59984(6) 0.0239(2) Uani 1 1 d . . . . . H4 H 0.351(3) 0.2239(18) 0.5524(12) 0.036 Uiso 1 1 d . U . . . O5 O 1.03520(16) 0.74015(10) 0.57855(7) 0.0381(3) Uani 1 1 d . . . . . O6 O 0.90684(15) 0.80472(9) 0.69288(6) 0.0314(2) Uani 1 1 d . . . . . O7 O 0.39026(19) 0.12488(11) 0.45862(7) 0.0425(3) 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 0.0212(6) 0.0131(5) 0.0209(6) 0.0015(4) 0.0017(5) 0.0002(4) C2 0.0193(6) 0.0135(5) 0.0196(6) 0.0012(4) 0.0009(4) 0.0004(4) C3 0.0198(6) 0.0127(5) 0.0210(6) 0.0011(4) 0.0005(5) -0.0001(4) C4 0.0211(6) 0.0163(5) 0.0259(6) 0.0048(5) 0.0008(5) 0.0027(4) C5 0.0205(6) 0.0194(6) 0.0330(7) 0.0059(5) 0.0043(5) 0.0041(4) C6 0.0198(6) 0.0165(5) 0.0284(6) 0.0040(5) 0.0033(5) 0.0008(4) C7 0.0301(7) 0.0155(5) 0.0228(6) 0.0002(5) 0.0054(5) 0.0000(5) C8 0.0341(7) 0.0138(5) 0.0261(6) -0.0003(5) 0.0076(5) 0.0028(5) C9 0.0268(6) 0.0130(5) 0.0238(6) 0.0003(4) 0.0031(5) -0.0001(4) C10 0.0310(7) 0.0179(6) 0.0355(7) 0.0044(5) 0.0116(6) 0.0072(5) C11 0.0174(5) 0.0150(5) 0.0225(6) 0.0020(4) 0.0027(4) -0.0009(4) C12 0.0179(5) 0.0172(5) 0.0201(6) 0.0020(4) 0.0013(4) -0.0006(4) C13 0.0218(6) 0.0141(5) 0.0248(6) 0.0001(4) 0.0001(5) 0.0001(4) C14 0.0206(6) 0.0162(5) 0.0271(6) 0.0048(5) 0.0015(5) 0.0002(4) C15 0.0171(5) 0.0208(6) 0.0206(6) 0.0041(5) 0.0007(5) -0.0009(4) C16 0.0199(6) 0.0173(5) 0.0217(6) 0.0010(4) 0.0025(5) -0.0012(4) C17 0.0199(6) 0.0144(5) 0.0201(6) 0.0036(4) -0.0011(5) 0.0025(4) C18 0.0217(6) 0.0143(5) 0.0213(6) 0.0029(4) -0.0027(5) 0.0012(4) C19 0.0245(6) 0.0191(6) 0.0209(6) 0.0015(4) -0.0003(5) 0.0055(5) C20 0.0203(6) 0.0229(6) 0.0237(6) 0.0061(5) 0.0023(5) 0.0048(5) C21 0.0191(6) 0.0158(5) 0.0248(6) 0.0058(4) -0.0020(5) 0.0005(4) C22 0.0203(6) 0.0157(5) 0.0208(6) 0.0033(4) -0.0016(5) 0.0026(4) C23 0.0393(8) 0.0221(6) 0.0234(6) -0.0004(5) -0.0074(6) 0.0091(5) C24 0.0686(14) 0.0508(11) 0.0737(14) 0.0314(10) -0.0303(11) -0.0213(10) C25 0.0836(15) 0.0801(15) 0.0342(9) 0.0023(9) 0.0107(10) 0.0470(12) N1 0.0218(5) 0.0225(5) 0.0230(5) 0.0049(4) 0.0003(4) -0.0033(4) N2 0.0218(5) 0.0193(5) 0.0275(6) 0.0064(4) 0.0004(4) -0.0008(4) O1 0.0308(5) 0.0141(4) 0.0199(4) -0.0002(3) -0.0020(4) -0.0005(3) O2 0.0363(5) 0.0262(5) 0.0277(5) 0.0120(4) -0.0035(4) -0.0021(4) O3 0.0468(6) 0.0265(5) 0.0238(5) -0.0015(4) -0.0049(4) -0.0005(4) O4 0.0287(5) 0.0157(4) 0.0235(5) -0.0021(3) 0.0004(4) -0.0034(3) O5 0.0327(6) 0.0343(5) 0.0434(6) 0.0047(5) 0.0159(5) -0.0073(4) O6 0.0335(5) 0.0224(5) 0.0318(5) -0.0018(4) 0.0024(4) -0.0090(4) O7 0.0584(7) 0.0343(6) 0.0329(6) -0.0113(4) -0.0057(5) 0.0129(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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 C1 C7 111.98(10) . . ? C11 C1 C6 110.39(9) . . ? C7 C1 C6 107.20(10) . . ? C11 C1 C2 109.39(9) . . ? C7 C1 C2 107.67(9) . . ? C6 C1 C2 110.15(10) . . ? C3 C2 C1 111.06(9) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C17 C3 C4 110.15(10) . . ? C17 C3 C9 111.48(9) . . ? C4 C3 C9 107.54(10) . . ? C17 C3 C2 110.18(9) . . ? C4 C3 C2 109.60(9) . . ? C9 C3 C2 107.83(10) . . ? C5 C4 C3 110.75(10) . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C10 C5 C6 109.45(11) . . ? C10 C5 C4 109.84(10) . . ? C6 C5 C4 109.76(10) . . ? C10 C5 H5 109.3 . . ? C6 C5 H5 109.3 . . ? C4 C5 H5 109.3 . . ? C5 C6 C1 110.72(9) . . ? 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 110.42(10) . . ? 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 C9 109.70(11) . . ? C10 C8 C7 110.10(10) . . ? C9 C8 C7 109.64(10) . . ? C10 C8 H8 109.1 . . ? C9 C8 H8 109.1 . . ? C7 C8 H8 109.1 . . ? C8 C9 C3 110.47(9) . . ? C8 C9 H9A 109.6 . . ? C3 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? C3 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? C5 C10 C8 108.38(10) . . ? 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 116.30(11) . . ? C16 C11 C1 121.48(10) . . ? C12 C11 C1 122.22(11) . . ? O1 C12 C13 119.55(10) . . ? O1 C12 C11 118.77(11) . . ? C13 C12 C11 121.68(11) . . ? C14 C13 C12 120.79(11) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 117.68(11) . . ? C13 C14 H14 121.2 . . ? C15 C14 H14 121.2 . . ? C14 C15 C16 122.30(12) . . ? C14 C15 N1 118.76(11) . . ? C16 C15 N1 118.93(10) . . ? C11 C16 C15 121.25(11) . . ? C11 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C22 C17 C18 116.64(11) . . ? C22 C17 C3 121.27(10) . . ? C18 C17 C3 122.09(10) . . ? O4 C18 C19 119.95(11) . . ? O4 C18 C17 118.48(11) . . ? C19 C18 C17 121.56(11) . . ? C20 C19 C18 120.60(11) . . ? C20 C19 H19 119.7 . . ? C18 C19 H19 119.7 . . ? C19 C20 C21 117.94(11) . . ? C19 C20 H20 121.0 . . ? C21 C20 H20 121.0 . . ? C20 C21 C22 122.47(11) . . ? C20 C21 N2 118.90(11) . . ? C22 C21 N2 118.60(11) . . ? C21 C22 C17 120.76(11) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? O7 C23 C24 121.86(17) . . ? O7 C23 C25 119.78(16) . . ? C24 C23 C25 118.37(17) . . ? 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 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O2 N1 O3 123.39(11) . . ? O2 N1 C15 118.12(10) . . ? O3 N1 C15 118.48(11) . . ? O5 N2 O6 122.69(10) . . ? O5 N2 C21 119.24(11) . . ? O6 N2 C21 118.06(10) . . ? C12 O1 H1 109.9(12) . . ? C18 O4 H4 110.3(12) . . ? 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 1.5310(16) . ? C1 C7 1.5415(16) . ? C1 C6 1.5443(17) . ? C1 C2 1.5508(16) . ? C2 C3 1.5496(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C17 1.5308(16) . ? C3 C4 1.5427(17) . ? C3 C9 1.5427(15) . ? C4 C5 1.5346(17) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.5294(18) . ? C5 C6 1.5318(17) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5362(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C10 1.530(2) . ? C8 C9 1.5360(17) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.3871(17) . ? C11 C12 1.4155(16) . ? C12 O1 1.3549(15) . ? C12 C13 1.3988(17) . ? C13 C14 1.3759(18) . ? C13 H13 0.9500 . ? C14 C15 1.3841(17) . ? C14 H14 0.9500 . ? C15 C16 1.3872(17) . ? C15 N1 1.4564(16) . ? C16 H16 0.9500 . ? C17 C22 1.3933(16) . ? C17 C18 1.4168(16) . ? C18 O4 1.3542(14) . ? C18 C19 1.4022(17) . ? C19 C20 1.3783(17) . ? C19 H19 0.9500 . ? C20 C21 1.3838(17) . ? C20 H20 0.9500 . ? C21 C22 1.3900(17) . ? C21 N2 1.4505(15) . ? C22 H22 0.9500 . ? C23 O7 1.2104(17) . ? C23 C24 1.479(2) . ? C23 C25 1.480(2) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N1 O2 1.2291(14) . ? N1 O3 1.2313(14) . ? N2 O5 1.2246(15) . ? N2 O6 1.2392(14) . ? O1 H1 0.875(18) . ? O4 H4 0.884(19) . ? 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 177.56(9) . . . . ? C7 C1 C2 C3 -60.54(13) . . . . ? C6 C1 C2 C3 56.05(12) . . . . ? C1 C2 C3 C17 -177.80(9) . . . . ? C1 C2 C3 C4 -56.44(12) . . . . ? C1 C2 C3 C9 60.34(12) . . . . ? C17 C3 C4 C5 179.66(9) . . . . ? C9 C3 C4 C5 -58.67(12) . . . . ? C2 C3 C4 C5 58.29(12) . . . . ? C3 C4 C5 C10 60.64(13) . . . . ? C3 C4 C5 C6 -59.75(13) . . . . ? C10 C5 C6 C1 -61.62(13) . . . . ? C4 C5 C6 C1 59.00(13) . . . . ? C11 C1 C6 C5 -178.12(10) . . . . ? C7 C1 C6 C5 59.67(12) . . . . ? C2 C1 C6 C5 -57.21(12) . . . . ? C11 C1 C7 C8 179.89(10) . . . . ? C6 C1 C7 C8 -58.90(12) . . . . ? C2 C1 C7 C8 59.60(13) . . . . ? C1 C7 C8 C10 60.77(13) . . . . ? C1 C7 C8 C9 -60.01(14) . . . . ? C10 C8 C9 C3 -61.28(13) . . . . ? C7 C8 C9 C3 59.74(14) . . . . ? C17 C3 C9 C8 179.76(10) . . . . ? C4 C3 C9 C8 58.93(13) . . . . ? C2 C3 C9 C8 -59.17(13) . . . . ? C6 C5 C10 C8 60.32(13) . . . . ? C4 C5 C10 C8 -60.26(13) . . . . ? C9 C8 C10 C5 60.61(12) . . . . ? C7 C8 C10 C5 -60.14(13) . . . . ? C7 C1 C11 C16 -2.44(16) . . . . ? C6 C1 C11 C16 -121.79(12) . . . . ? C2 C1 C11 C16 116.85(12) . . . . ? C7 C1 C11 C12 176.97(11) . . . . ? C6 C1 C11 C12 57.61(14) . . . . ? C2 C1 C11 C12 -63.75(14) . . . . ? C16 C11 C12 O1 -178.99(10) . . . . ? C1 C11 C12 O1 1.57(17) . . . . ? C16 C11 C12 C13 0.56(17) . . . . ? C1 C11 C12 C13 -178.87(11) . . . . ? O1 C12 C13 C14 179.16(11) . . . . ? C11 C12 C13 C14 -0.39(18) . . . . ? C12 C13 C14 C15 -0.15(18) . . . . ? C13 C14 C15 C16 0.52(18) . . . . ? C13 C14 C15 N1 179.83(11) . . . . ? C12 C11 C16 C15 -0.20(17) . . . . ? C1 C11 C16 C15 179.24(11) . . . . ? C14 C15 C16 C11 -0.35(18) . . . . ? N1 C15 C16 C11 -179.66(11) . . . . ? C4 C3 C17 C22 117.00(12) . . . . ? C9 C3 C17 C22 -2.29(16) . . . . ? C2 C3 C17 C22 -121.97(12) . . . . ? C4 C3 C17 C18 -63.02(14) . . . . ? C9 C3 C17 C18 177.69(11) . . . . ? C2 C3 C17 C18 58.01(15) . . . . ? C22 C17 C18 O4 -177.58(11) . . . . ? C3 C17 C18 O4 2.44(18) . . . . ? C22 C17 C18 C19 1.59(18) . . . . ? C3 C17 C18 C19 -178.39(11) . . . . ? O4 C18 C19 C20 177.67(11) . . . . ? C17 C18 C19 C20 -1.49(19) . . . . ? C18 C19 C20 C21 0.80(19) . . . . ? C19 C20 C21 C22 -0.31(19) . . . . ? C19 C20 C21 N2 177.38(11) . . . . ? C20 C21 C22 C17 0.48(19) . . . . ? N2 C21 C22 C17 -177.22(11) . . . . ? C18 C17 C22 C21 -1.08(18) . . . . ? C3 C17 C22 C21 178.90(11) . . . . ? C14 C15 N1 O2 3.76(17) . . . . ? C16 C15 N1 O2 -176.90(11) . . . . ? C14 C15 N1 O3 -176.78(11) . . . . ? C16 C15 N1 O3 2.56(17) . . . . ? C20 C21 N2 O5 0.14(18) . . . . ? C22 C21 N2 O5 177.92(12) . . . . ? C20 C21 N2 O6 -179.04(11) . . . . ? C22 C21 N2 O6 -1.26(17) . . . . ?