#------------------------------------------------------------------------------ #$Date: 2023-10-28 01:40:51 +0300 (Sat, 28 Oct 2023) $ #$Revision: 287151 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247593.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_7247593 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_name_full CrystEngComm _journal_paper_doi 10.1039/D3CE00775H _journal_year 2023 _chemical_formula_sum 'C26 H30 N2 O7' _chemical_formula_weight 482.52 _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 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 95.513(6) _cell_angle_beta 93.850(6) _cell_angle_gamma 100.486(5) _cell_formula_units_Z 2 _cell_length_a 7.0766(14) _cell_length_b 10.505(2) _cell_length_c 15.939(3) _cell_measurement_reflns_used 9104 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 79.02 _cell_measurement_theta_min 2.80 _cell_volume 1155.4(4) _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 0.949 _diffrn_measured_fraction_theta_max 0.901 _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 0.0239 _diffrn_reflns_Laue_measured_fraction_full 0.949 _diffrn_reflns_Laue_measured_fraction_max 0.901 _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 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 15824 _diffrn_reflns_point_group_measured_fraction_full 0.949 _diffrn_reflns_point_group_measured_fraction_max 0.901 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 79.471 _diffrn_reflns_theta_min 2.795 _diffrn_source 'rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 0.836 _exptl_absorpt_correction_T_max 0.9288 _exptl_absorpt_correction_T_min 0.8190 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.387 _exptl_crystal_description prismatic _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.258 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.040 _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 372 _refine_ls_number_reflns 4522 _refine_ls_number_restraints 24 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0381 _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^)+(0.0507P)^2^+0.4491P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1028 _refine_ls_wR_factor_ref 0.1040 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4385 _reflns_number_total 4522 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00775h2.cif _cod_data_source_block 1b _cod_database_code 7247593 _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 0.885 _shelx_estimated_absorpt_t_max 0.921 _shelx_res_file ; TITL P-1_a.res in P-1 P-1_a.res created by SHELXL-2018/3 at 13:52:13 on 14-Dec-2022 REM Old TITL P-1 in P-1 REM SHELXT solution in P-1: R1 0.160, Rweak 0.046, Alpha 0.055 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C28 O7 CELL 1.54178 7.0766 10.5052 15.9394 95.513 93.850 100.486 ZERR 2.000 0.0014 0.0022 0.0032 0.006 0.006 0.005 LATT 1 SFAC C H N O UNIT 52 60 4 14 OMIT 3 10 6 OMIT 3 10 7 OMIT 5 7 7 OMIT 4 8 8 OMIT 4 9 6 OMIT 4 8 9 OMIT 4 7 10 OMIT 4 8 7 OMIT 5 8 6 OMIT 5 7 8 OMIT 5 8 4 OMIT 3 9 9 OMIT 4 9 5 OMIT 4 9 4 OMIT 5 8 5 OMIT 0 1 2 OMIT -1 3 2 OMIT 4 9 7 TEMP -173.000 SIZE 0.10 0.10 0.15 REM colourless prismatic L.S. 10 ACTA CONF WPDB -2 BOND $H LIST 4 FMAP 2 PLAN 10 WGHT 0.050700 0.449100 FVAR 1.00773 0.81106 C1 1 0.196658 0.293368 0.858222 11.00000 0.02452 0.01207 = 0.02098 0.00102 0.00497 0.00136 C2 1 0.344341 0.315632 0.791066 11.00000 0.01977 0.01271 = 0.01907 0.00038 0.00195 0.00155 AFIX 23 H2A 2 0.316354 0.241502 0.745943 11.00000 -1.20000 H2B 2 0.475873 0.319360 0.817829 11.00000 -1.20000 AFIX 0 C3 1 0.336117 0.444066 0.751500 11.00000 0.02101 0.01267 = 0.02103 0.00144 0.00424 0.00090 C4 1 0.128618 0.441188 0.712804 11.00000 0.02222 0.01720 = 0.02992 0.00782 0.00458 0.00420 AFIX 23 H4A 2 0.122985 0.523919 0.688643 11.00000 -1.20000 H4B 2 0.093186 0.369106 0.666478 11.00000 -1.20000 AFIX 0 C5 1 -0.015395 0.422306 0.780494 11.00000 0.02417 0.02121 = 0.03997 0.01198 0.01089 0.00844 AFIX 13 H5 2 -0.148477 0.419874 0.754148 11.00000 -1.20000 AFIX 0 C6 1 -0.008352 0.293745 0.817650 11.00000 0.02279 0.01898 = 0.03164 0.00802 0.00882 0.00468 AFIX 23 H6A 2 -0.045414 0.220293 0.772315 11.00000 -1.20000 H6B 2 -0.102016 0.281656 0.860978 11.00000 -1.20000 AFIX 0 C7 1 0.247716 0.408904 0.927974 11.00000 0.03964 0.01553 = 0.02193 0.00021 0.01033 0.00190 AFIX 23 H7A 2 0.155911 0.397059 0.972063 11.00000 -1.20000 H7B 2 0.379013 0.412000 0.954794 11.00000 -1.20000 AFIX 0 C8 1 0.383816 0.556996 0.823471 11.00000 0.03394 0.01231 = 0.02505 0.00080 0.00826 0.00050 AFIX 23 H8A 2 0.515918 0.561276 0.849769 11.00000 -1.20000 H8B 2 0.379405 0.640445 0.800051 11.00000 -1.20000 AFIX 0 C9 1 0.239153 0.537339 0.890727 11.00000 0.04687 0.01230 = 0.02916 -0.00043 0.01627 0.00404 AFIX 13 H9 2 0.273550 0.611065 0.936970 11.00000 -1.20000 AFIX 0 C10 1 0.035311 0.534971 0.851068 11.00000 0.04417 0.02016 = 0.04607 0.01007 0.02510 0.01446 AFIX 23 H10A 2 -0.058118 0.523390 0.894523 11.00000 -1.20000 H10B 2 0.029408 0.618348 0.827803 11.00000 -1.20000 AFIX 0 C11 1 0.202922 0.163404 0.893355 11.00000 0.01975 0.01421 = 0.02166 0.00167 0.00434 0.00077 C12 1 0.151446 0.042472 0.842567 11.00000 0.02000 0.01773 = 0.01991 0.00225 0.00222 0.00180 C13 1 0.157581 -0.074931 0.875995 11.00000 0.02518 0.01380 = 0.02442 0.00003 0.00231 0.00065 AFIX 43 H13 2 0.121432 -0.154671 0.840250 11.00000 -1.20000 AFIX 0 C14 1 0.215459 -0.076772 0.960289 11.00000 0.02267 0.01726 = 0.02627 0.00656 0.00408 0.00256 AFIX 43 H14 2 0.220750 -0.156450 0.983116 11.00000 -1.20000 AFIX 0 C15 1 0.265350 0.041065 1.010237 11.00000 0.01866 0.02221 = 0.01920 0.00443 0.00293 0.00055 C16 1 0.259297 0.158538 0.978233 11.00000 0.02172 0.01643 = 0.02109 0.00012 0.00434 -0.00068 AFIX 43 H16 2 0.294329 0.237362 1.014960 11.00000 -1.20000 AFIX 0 C17 1 0.477202 0.461836 0.682922 11.00000 0.01949 0.01542 = 0.01903 0.00293 0.00078 0.00268 C18 1 0.467341 0.367412 0.612014 11.00000 0.02050 0.01755 = 0.02087 0.00207 -0.00009 0.00146 C19 1 0.600374 0.383583 0.550754 11.00000 0.02558 0.02377 = 0.02053 -0.00099 0.00274 0.00465 AFIX 43 H19 2 0.593306 0.317346 0.505046 11.00000 -1.20000 AFIX 0 C20 1 0.740519 0.493596 0.555851 11.00000 0.02180 0.02949 = 0.02246 0.00569 0.00522 0.00527 AFIX 43 H20 2 0.830062 0.505026 0.514127 11.00000 -1.20000 AFIX 0 C21 1 0.747412 0.587743 0.623914 11.00000 0.01831 0.01987 = 0.02379 0.00571 -0.00016 0.00008 C22 1 0.620056 0.572438 0.686674 11.00000 0.02102 0.01652 = 0.01966 0.00264 0.00034 0.00191 AFIX 43 H22 2 0.631076 0.638619 0.732713 11.00000 -1.20000 AFIX 0 N1 3 0.324432 0.042461 1.099910 11.00000 0.02356 0.02545 = 0.02237 0.00573 0.00274 -0.00185 N2 3 0.893513 0.705218 0.630684 11.00000 0.02278 0.02296 = 0.02629 0.00777 0.00172 -0.00138 O1 4 0.095184 0.040992 0.759105 11.00000 0.03365 0.01497 = 0.02093 0.00042 -0.00323 0.00090 H1 2 0.060171 -0.039876 0.736524 11.00000 -1.50000 O2 4 0.347586 -0.060571 1.125935 11.00000 0.03897 0.02936 = 0.02784 0.01366 -0.00081 0.00095 O3 4 0.347906 0.146383 1.145680 11.00000 0.05290 0.03017 = 0.02229 -0.00062 -0.00236 0.00127 O4 4 0.325851 0.260806 0.604287 11.00000 0.02775 0.01940 = 0.02309 -0.00397 0.00277 -0.00350 H4 2 0.335831 0.215381 0.558441 11.00000 -1.50000 O5 4 1.003536 0.719243 0.574615 11.00000 0.03582 0.04167 = 0.03825 0.00789 0.01517 -0.01015 O6 4 0.901699 0.786580 0.693173 11.00000 0.03236 0.02269 = 0.03334 0.00032 0.00236 -0.00795 PART 1 C23 1 0.306231 0.008592 0.414773 21.00000 0.02765 0.02142 = 0.01916 0.00287 -0.00194 0.00130 C24 1 0.140892 -0.100158 0.425965 21.00000 0.04725 0.05049 = 0.04838 0.02442 -0.00791 -0.02798 AFIX 137 H24A 2 0.027497 -0.092804 0.389260 21.00000 -1.50000 H24B 2 0.110204 -0.093806 0.485089 21.00000 -1.50000 H24C 2 0.177823 -0.184344 0.410801 21.00000 -1.50000 AFIX 0 C25 1 0.407368 -0.005401 0.335674 21.00000 0.03663 0.02858 = 0.01910 -0.00343 0.00068 0.01023 AFIX 23 H25A 2 0.312268 -0.014713 0.285952 21.00000 -1.20000 H25B 2 0.462134 -0.085775 0.334106 21.00000 -1.20000 AFIX 0 C26 1 0.570542 0.111708 0.329513 21.00000 0.02275 0.04731 = 0.03637 0.01095 0.00660 0.00310 AFIX 137 H26A 2 0.620005 0.103750 0.273656 21.00000 -1.50000 H26B 2 0.675039 0.113196 0.373388 21.00000 -1.50000 H26C 2 0.520284 0.192604 0.337580 21.00000 -1.50000 AFIX 0 O7 4 0.356023 0.104787 0.466446 21.00000 0.04441 0.03293 = 0.02463 -0.01040 0.00819 -0.00240 PART 2 SIMU 0.001 c23b > o7b C23B 1 0.412929 0.057696 0.389494 -21.00000 0.06836 0.05239 = 0.02732 0.00002 -0.00080 0.02310 C24B 1 0.570885 0.072946 0.334716 -21.00000 0.06844 0.05346 = 0.02752 0.00070 -0.00021 0.02206 AFIX 137 H24D 2 0.519323 0.047148 0.275700 -21.00000 -1.50000 H24E 2 0.662274 0.017723 0.350446 -21.00000 -1.50000 H24F 2 0.637118 0.164209 0.341222 -21.00000 -1.50000 AFIX 0 C25B 1 0.308847 -0.065860 0.360360 -21.00000 0.06910 0.05305 = 0.02818 0.00056 -0.00198 0.02255 AFIX 23 H25C 2 0.393432 -0.131305 0.358565 -21.00000 -1.20000 H25D 2 0.243627 -0.067253 0.303262 -21.00000 -1.20000 AFIX 0 C26B 1 0.161679 -0.091019 0.426237 -21.00000 0.06871 0.05292 = 0.02791 0.00069 -0.00368 0.02382 AFIX 137 H26D 2 0.210091 -0.141729 0.468547 -21.00000 -1.50000 H26E 2 0.038806 -0.139720 0.398116 -21.00000 -1.50000 H26F 2 0.142199 -0.007667 0.454099 -21.00000 -1.50000 AFIX 0 O7B 4 0.369734 0.123831 0.450085 -21.00000 0.07003 0.05131 = 0.02770 -0.00337 0.00214 0.02310 HKLF 4 REM P-1_a.res in P-1 REM wR2 = 0.1040, GooF = S = 1.058, Restrained GooF = 1.057 for all data REM R1 = 0.0381 for 4385 Fo > 4sig(Fo) and 0.0389 for all 4522 data REM 372 parameters refined using 24 restraints END WGHT 0.0507 0.4491 REM Highest difference peak 0.258, deepest hole -0.226, 1-sigma level 0.040 Q1 1 0.3109 0.5461 0.8588 11.00000 0.05 0.26 Q2 1 0.2349 0.4665 0.9028 11.00000 0.05 0.25 Q3 1 0.2293 0.3503 0.8921 11.00000 0.05 0.24 Q4 1 0.4072 0.4541 0.7165 11.00000 0.05 0.24 Q5 1 0.1466 -0.0161 0.8661 11.00000 0.05 0.24 Q6 1 0.1995 0.2245 0.8762 11.00000 0.05 0.23 Q7 1 0.0953 0.2955 0.8429 11.00000 0.05 0.23 Q8 1 0.2604 0.3018 0.8241 11.00000 0.05 0.22 Q9 1 0.3472 0.3838 0.7708 11.00000 0.05 0.22 Q10 1 -0.0136 0.3640 0.7988 11.00000 0.05 0.22 ; _shelx_res_checksum 87440 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 0.19666(17) 0.29337(10) 0.85822(7) 0.0194(2) Uani 1 1 d . . . . . C2 C 0.34434(16) 0.31563(10) 0.79107(7) 0.0175(2) Uani 1 1 d . . . . . H2A H 0.316354 0.241502 0.745943 0.021 Uiso 1 1 calc R U . . . H2B H 0.475873 0.319360 0.817829 0.021 Uiso 1 1 calc R U . . . C3 C 0.33612(16) 0.44407(10) 0.75150(7) 0.0184(2) Uani 1 1 d . . . . . C4 C 0.12862(17) 0.44119(11) 0.71280(8) 0.0226(2) Uani 1 1 d . . . . . H4A H 0.122985 0.523919 0.688643 0.027 Uiso 1 1 calc R U . . . H4B H 0.093186 0.369106 0.666478 0.027 Uiso 1 1 calc R U . . . C5 C -0.01539(18) 0.42231(12) 0.78049(9) 0.0270(3) Uani 1 1 d . . . . . H5 H -0.148477 0.419874 0.754148 0.032 Uiso 1 1 calc R U . . . C6 C -0.00835(17) 0.29374(11) 0.81765(8) 0.0237(3) Uani 1 1 d . . . . . H6A H -0.045414 0.220293 0.772315 0.028 Uiso 1 1 calc R U . . . H6B H -0.102016 0.281656 0.860978 0.028 Uiso 1 1 calc R U . . . C7 C 0.2477(2) 0.40890(11) 0.92797(8) 0.0259(3) Uani 1 1 d . . . . . H7A H 0.155911 0.397059 0.972063 0.031 Uiso 1 1 calc R U . . . H7B H 0.379013 0.412000 0.954794 0.031 Uiso 1 1 calc R U . . . C8 C 0.38382(19) 0.55700(11) 0.82347(8) 0.0241(3) Uani 1 1 d . . . . . H8A H 0.515918 0.561276 0.849769 0.029 Uiso 1 1 calc R U . . . H8B H 0.379405 0.640445 0.800051 0.029 Uiso 1 1 calc R U . . . C9 C 0.2392(2) 0.53734(11) 0.89073(8) 0.0292(3) Uani 1 1 d . . . . . H9 H 0.273550 0.611065 0.936970 0.035 Uiso 1 1 calc R U . . . C10 C 0.0353(2) 0.53497(12) 0.85107(9) 0.0343(3) Uani 1 1 d . . . . . H10A H -0.058118 0.523390 0.894523 0.041 Uiso 1 1 calc R U . . . H10B H 0.029408 0.618348 0.827803 0.041 Uiso 1 1 calc R U . . . C11 C 0.20292(16) 0.16340(10) 0.89335(7) 0.0188(2) Uani 1 1 d . . . . . C12 C 0.15145(16) 0.04247(11) 0.84257(7) 0.0194(2) Uani 1 1 d . . . . . C13 C 0.15758(17) -0.07493(11) 0.87600(7) 0.0217(2) Uani 1 1 d . . . . . H13 H 0.121432 -0.154671 0.840250 0.026 Uiso 1 1 calc R U . . . C14 C 0.21546(17) -0.07677(11) 0.96029(7) 0.0219(2) Uani 1 1 d . . . . . H14 H 0.220750 -0.156450 0.983116 0.026 Uiso 1 1 calc R U . . . C15 C 0.26535(16) 0.04106(11) 1.01024(7) 0.0202(2) Uani 1 1 d . . . . . C16 C 0.25930(17) 0.15854(11) 0.97823(7) 0.0203(2) Uani 1 1 d . . . . . H16 H 0.294329 0.237362 1.014960 0.024 Uiso 1 1 calc R U . . . C17 C 0.47720(16) 0.46184(10) 0.68292(7) 0.0180(2) Uani 1 1 d . . . . . C18 C 0.46734(17) 0.36741(11) 0.61201(7) 0.0200(2) Uani 1 1 d . . . . . C19 C 0.60037(18) 0.38358(12) 0.55075(7) 0.0235(2) Uani 1 1 d . . . . . H19 H 0.593306 0.317346 0.505046 0.028 Uiso 1 1 calc R U . . . C20 C 0.74052(17) 0.49360(12) 0.55585(7) 0.0242(3) Uani 1 1 d . . . . . H20 H 0.830062 0.505026 0.514127 0.029 Uiso 1 1 calc R U . . . C21 C 0.74741(16) 0.58774(11) 0.62391(7) 0.0210(2) Uani 1 1 d . . . . . C22 C 0.62006(16) 0.57244(11) 0.68667(7) 0.0193(2) Uani 1 1 d . . . . . H22 H 0.631076 0.638619 0.732713 0.023 Uiso 1 1 calc R U . . . N1 N 0.32443(15) 0.04246(10) 1.09991(6) 0.0244(2) Uani 1 1 d . . . . . N2 N 0.89351(15) 0.70522(10) 0.63068(6) 0.0244(2) Uani 1 1 d . . . . . O1 O 0.09518(13) 0.04099(8) 0.75911(5) 0.02401(19) Uani 1 1 d . . . . . H1 H 0.060(2) -0.0399(17) 0.7365(10) 0.036 Uiso 1 1 d . U . . . O2 O 0.34759(14) -0.06057(9) 1.12594(6) 0.0322(2) Uani 1 1 d . . . . . O3 O 0.34791(16) 0.14638(9) 1.14568(6) 0.0365(2) Uani 1 1 d . . . . . O4 O 0.32585(13) 0.26081(8) 0.60429(5) 0.0248(2) Uani 1 1 d . . . . . H4 H 0.336(3) 0.2154(17) 0.5584(11) 0.037 Uiso 1 1 d . U . . . O5 O 1.00354(15) 0.71924(10) 0.57462(6) 0.0400(3) Uani 1 1 d . . . . . O6 O 0.90170(14) 0.78658(9) 0.69317(6) 0.0313(2) Uani 1 1 d . . . . . C23 C 0.3062(2) 0.00859(15) 0.41477(9) 0.0233(4) Uani 0.811(5) 1 d . . P A 1 C24 C 0.1409(6) -0.1002(4) 0.4260(3) 0.0527(9) Uani 0.811(5) 1 d . . P A 1 H24A H 0.027497 -0.092804 0.389260 0.079 Uiso 0.811(5) 1 calc R U P A 1 H24B H 0.110204 -0.093806 0.485089 0.079 Uiso 0.811(5) 1 calc R U P A 1 H24C H 0.177823 -0.184344 0.410801 0.079 Uiso 0.811(5) 1 calc R U P A 1 C25 C 0.4074(3) -0.00540(16) 0.33567(10) 0.0281(5) Uani 0.811(5) 1 d . . P A 1 H25A H 0.312268 -0.014713 0.285952 0.034 Uiso 0.811(5) 1 calc R U P A 1 H25B H 0.462134 -0.085775 0.334106 0.034 Uiso 0.811(5) 1 calc R U P A 1 C26 C 0.5705(4) 0.1117(2) 0.3295(2) 0.0353(6) Uani 0.811(5) 1 d . . P A 1 H26A H 0.620005 0.103750 0.273656 0.053 Uiso 0.811(5) 1 calc R U P A 1 H26B H 0.675039 0.113196 0.373388 0.053 Uiso 0.811(5) 1 calc R U P A 1 H26C H 0.520284 0.192604 0.337580 0.053 Uiso 0.811(5) 1 calc R U P A 1 O7 O 0.3560(5) 0.1048(3) 0.46645(15) 0.0359(5) Uani 0.811(5) 1 d . . P A 1 C23B C 0.4129(17) 0.0577(10) 0.3895(5) 0.048(2) Uani 0.189(5) 1 d . U P A 2 C24B C 0.571(3) 0.0729(15) 0.3347(10) 0.049(2) Uani 0.189(5) 1 d . U P A 2 H24D H 0.519323 0.047148 0.275700 0.073 Uiso 0.189(5) 1 calc R U P A 2 H24E H 0.662274 0.017723 0.350446 0.073 Uiso 0.189(5) 1 calc R U P A 2 H24F H 0.637118 0.164209 0.341222 0.073 Uiso 0.189(5) 1 calc R U P A 2 C25B C 0.3088(17) -0.0659(10) 0.3604(5) 0.049(2) Uani 0.189(5) 1 d . U P A 2 H25C H 0.393432 -0.131305 0.358565 0.059 Uiso 0.189(5) 1 calc R U P A 2 H25D H 0.243627 -0.067253 0.303262 0.059 Uiso 0.189(5) 1 calc R U P A 2 C26B C 0.162(3) -0.0910(19) 0.4262(13) 0.049(2) Uani 0.189(5) 1 d . U P A 2 H26D H 0.210091 -0.141729 0.468547 0.073 Uiso 0.189(5) 1 calc R U P A 2 H26E H 0.038806 -0.139720 0.398116 0.073 Uiso 0.189(5) 1 calc R U P A 2 H26F H 0.142199 -0.007667 0.454099 0.073 Uiso 0.189(5) 1 calc R U P A 2 O7B O 0.370(3) 0.1238(17) 0.4501(9) 0.049(2) Uani 0.189(5) 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 0.0245(6) 0.0121(5) 0.0210(5) 0.0010(4) 0.0050(4) 0.0014(4) C2 0.0198(5) 0.0127(5) 0.0191(5) 0.0004(4) 0.0020(4) 0.0016(4) C3 0.0210(5) 0.0127(5) 0.0210(5) 0.0014(4) 0.0042(4) 0.0009(4) C4 0.0222(6) 0.0172(5) 0.0299(6) 0.0078(5) 0.0046(5) 0.0042(4) C5 0.0242(6) 0.0212(6) 0.0400(7) 0.0120(5) 0.0109(5) 0.0084(5) C6 0.0228(6) 0.0190(5) 0.0316(6) 0.0080(5) 0.0088(5) 0.0047(5) C7 0.0396(7) 0.0155(5) 0.0219(6) 0.0002(4) 0.0103(5) 0.0019(5) C8 0.0339(7) 0.0123(5) 0.0251(6) 0.0008(4) 0.0083(5) 0.0005(5) C9 0.0469(8) 0.0123(5) 0.0292(6) -0.0004(5) 0.0163(6) 0.0040(5) C10 0.0442(8) 0.0202(6) 0.0461(8) 0.0101(6) 0.0251(6) 0.0145(6) C11 0.0197(5) 0.0142(5) 0.0217(5) 0.0017(4) 0.0043(4) 0.0008(4) C12 0.0200(5) 0.0177(5) 0.0199(5) 0.0022(4) 0.0022(4) 0.0018(4) C13 0.0252(6) 0.0138(5) 0.0244(6) 0.0000(4) 0.0023(4) 0.0007(4) C14 0.0227(6) 0.0173(5) 0.0263(6) 0.0066(4) 0.0041(4) 0.0026(4) C15 0.0187(5) 0.0222(6) 0.0192(5) 0.0044(4) 0.0029(4) 0.0005(4) C16 0.0217(5) 0.0164(5) 0.0211(5) 0.0001(4) 0.0043(4) -0.0007(4) C17 0.0195(5) 0.0154(5) 0.0190(5) 0.0029(4) 0.0008(4) 0.0027(4) C18 0.0205(5) 0.0175(5) 0.0209(5) 0.0021(4) -0.0001(4) 0.0015(4) C19 0.0256(6) 0.0238(6) 0.0205(5) -0.0010(4) 0.0027(4) 0.0047(5) C20 0.0218(6) 0.0295(6) 0.0225(5) 0.0057(5) 0.0052(4) 0.0053(5) C21 0.0183(5) 0.0199(5) 0.0238(5) 0.0057(4) -0.0002(4) 0.0001(4) C22 0.0210(5) 0.0165(5) 0.0197(5) 0.0026(4) 0.0003(4) 0.0019(4) N1 0.0236(5) 0.0254(5) 0.0224(5) 0.0057(4) 0.0027(4) -0.0018(4) N2 0.0228(5) 0.0230(5) 0.0263(5) 0.0078(4) 0.0017(4) -0.0014(4) O1 0.0336(5) 0.0150(4) 0.0209(4) 0.0004(3) -0.0032(3) 0.0009(3) O2 0.0390(5) 0.0294(5) 0.0278(5) 0.0137(4) -0.0008(4) 0.0010(4) O3 0.0529(6) 0.0302(5) 0.0223(4) -0.0006(4) -0.0024(4) 0.0013(5) O4 0.0277(5) 0.0194(4) 0.0231(4) -0.0040(3) 0.0028(3) -0.0035(3) O5 0.0358(6) 0.0417(6) 0.0383(5) 0.0079(4) 0.0152(4) -0.0102(5) O6 0.0324(5) 0.0227(4) 0.0333(5) 0.0003(4) 0.0024(4) -0.0079(4) C23 0.0276(9) 0.0214(8) 0.0192(7) 0.0029(6) -0.0019(6) 0.0013(6) C24 0.0472(16) 0.0505(15) 0.0484(14) 0.0244(12) -0.0079(12) -0.0280(12) C25 0.0366(10) 0.0286(9) 0.0191(8) -0.0034(6) 0.0007(6) 0.0102(8) C26 0.0228(9) 0.0473(15) 0.0364(11) 0.0109(11) 0.0066(7) 0.0031(10) O7 0.0444(9) 0.0329(10) 0.0246(11) -0.0104(8) 0.0082(8) -0.0024(7) C23B 0.068(4) 0.052(4) 0.027(3) 0.000(2) -0.001(2) 0.023(3) C24B 0.068(4) 0.053(4) 0.028(3) 0.001(3) 0.000(3) 0.022(4) C25B 0.069(4) 0.053(4) 0.028(3) 0.001(2) -0.002(2) 0.023(3) C26B 0.069(5) 0.053(4) 0.028(3) 0.001(3) -0.004(3) 0.024(4) O7B 0.070(5) 0.051(4) 0.028(3) -0.003(3) 0.002(3) 0.023(4) 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 111.80(9) . . ? C11 C1 C6 110.25(9) . . ? C7 C1 C6 107.56(9) . . ? C11 C1 C2 109.79(9) . . ? C7 C1 C2 107.75(9) . . ? C6 C1 C2 109.62(9) . . ? C1 C2 C3 111.17(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 . . ? C17 C3 C8 111.64(9) . . ? C17 C3 C4 109.74(9) . . ? C8 C3 C4 107.54(9) . . ? C17 C3 C2 110.47(9) . . ? C8 C3 C2 107.74(9) . . ? C4 C3 C2 109.64(9) . . ? C5 C4 C3 110.54(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 109.37(11) . . ? C10 C5 C4 109.84(10) . . ? C6 C5 C4 109.75(9) . . ? C10 C5 H5 109.3 . . ? C6 C5 H5 109.3 . . ? C4 C5 H5 109.3 . . ? C5 C6 C1 110.75(10) . . ? 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 . . ? C9 C7 C1 110.43(10) . . ? C9 C7 H7A 109.6 . . ? C1 C7 H7A 109.6 . . ? C9 C7 H7B 109.6 . . ? C1 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C3 110.49(10) . . ? C9 C8 H8A 109.6 . . ? C3 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C3 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 109.81(11) . . ? C10 C9 C7 110.00(11) . . ? C8 C9 C7 109.64(10) . . ? C10 C9 H9 109.1 . . ? C8 C9 H9 109.1 . . ? C7 C9 H9 109.1 . . ? C5 C10 C9 108.65(10) . . ? C5 C10 H10A 110.0 . . ? C9 C10 H10A 110.0 . . ? C5 C10 H10B 110.0 . . ? C9 C10 H10B 110.0 . . ? H10A C10 H10B 108.3 . . ? C16 C11 C12 116.26(10) . . ? C16 C11 C1 121.22(10) . . ? C12 C11 C1 122.51(10) . . ? O1 C12 C13 119.48(10) . . ? O1 C12 C11 118.96(10) . . ? C13 C12 C11 121.56(10) . . ? C14 C13 C12 120.93(10) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 117.74(10) . . ? C15 C14 H14 121.1 . . ? C13 C14 H14 121.1 . . ? C14 C15 C16 122.12(11) . . ? C14 C15 N1 119.14(10) . . ? C16 C15 N1 118.73(10) . . ? C15 C16 C11 121.38(10) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C22 C17 C18 116.68(10) . . ? C22 C17 C3 121.38(10) . . ? C18 C17 C3 121.94(10) . . ? O4 C18 C19 120.17(10) . . ? O4 C18 C17 118.54(10) . . ? C19 C18 C17 121.29(11) . . ? C20 C19 C18 120.96(11) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 117.89(11) . . ? C19 C20 H20 121.1 . . ? C21 C20 H20 121.1 . . ? C20 C21 C22 122.21(11) . . ? C20 C21 N2 119.05(10) . . ? C22 C21 N2 118.73(11) . . ? C17 C22 C21 120.92(11) . . ? C17 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? O2 N1 O3 123.33(10) . . ? O2 N1 C15 118.19(10) . . ? O3 N1 C15 118.48(10) . . ? O5 N2 O6 123.15(11) . . ? O5 N2 C21 118.54(11) . . ? O6 N2 C21 118.32(10) . . ? C12 O1 H1 109.0(11) . . ? C18 O4 H4 107.7(12) . . ? O7 C23 C25 120.6(2) . . ? O7 C23 C24 122.7(3) . . ? C25 C23 C24 116.8(2) . . ? 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 C26 112.65(16) . . ? C23 C25 H25A 109.1 . . ? C26 C25 H25A 109.1 . . ? C23 C25 H25B 109.1 . . ? C26 C25 H25B 109.1 . . ? H25A C25 H25B 107.8 . . ? 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 . . ? O7B C23B C25B 122.5(12) . . ? O7B C23B C24B 134.6(13) . . ? C25B C23B C24B 102.8(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 . . ? C23B C25B C26B 103.0(10) . . ? C23B C25B H25C 111.2 . . ? C26B C25B H25C 111.2 . . ? C23B C25B H25D 111.2 . . ? C26B C25B H25D 111.2 . . ? H25C C25B H25D 109.1 . . ? C25B C26B H26D 109.5 . . ? C25B C26B H26E 109.5 . . ? H26D C26B H26E 109.5 . . ? C25B C26B H26F 109.5 . . ? H26D C26B H26F 109.5 . . ? H26E C26B H26F 109.5 . . ? 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 1.5314(15) . ? C1 C7 1.5385(16) . ? C1 C6 1.5491(17) . ? C1 C2 1.5499(15) . ? C2 C3 1.5520(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C17 1.5311(15) . ? C3 C8 1.5421(16) . ? C3 C4 1.5479(16) . ? C4 C5 1.5353(16) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.527(2) . ? C5 C6 1.5335(16) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C9 1.5347(16) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5339(16) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.531(2) . ? C9 H9 1.0000 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.3930(16) . ? C11 C12 1.4129(16) . ? C12 O1 1.3606(14) . ? C12 C13 1.3963(16) . ? C13 C14 1.3811(17) . ? C13 H13 0.9500 . ? C14 C15 1.3801(17) . ? C14 H14 0.9500 . ? C15 C16 1.3865(16) . ? C15 N1 1.4600(15) . ? C16 H16 0.9500 . ? C17 C22 1.3880(16) . ? C17 C18 1.4195(15) . ? C18 O4 1.3493(14) . ? C18 C19 1.4020(16) . ? C19 C20 1.3711(18) . ? C19 H19 0.9500 . ? C20 C21 1.3881(17) . ? C20 H20 0.9500 . ? C21 C22 1.3921(16) . ? C21 N2 1.4486(15) . ? C22 H22 0.9500 . ? N1 O2 1.2297(14) . ? N1 O3 1.2314(14) . ? N2 O5 1.2262(14) . ? N2 O6 1.2396(14) . ? O1 H1 0.875(18) . ? O4 H4 0.848(18) . ? C23 O7 1.223(3) . ? C23 C25 1.499(2) . ? C23 C24 1.512(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.542(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C23B O7B 1.223(18) . ? C23B C25B 1.390(16) . ? C23B C24B 1.46(2) . ? C24B H24D 0.9800 . ? C24B H24E 0.9800 . ? C24B H24F 0.9800 . ? C25B C26B 1.54(2) . ? C25B H25C 0.9900 . ? C25B H25D 0.9900 . ? C26B H26D 0.9800 . ? C26B H26E 0.9800 . ? C26B H26F 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 177.75(9) . . . . ? C7 C1 C2 C3 -60.27(12) . . . . ? C6 C1 C2 C3 56.50(12) . . . . ? C1 C2 C3 C17 -177.80(9) . . . . ? C1 C2 C3 C8 60.02(12) . . . . ? C1 C2 C3 C4 -56.73(12) . . . . ? C17 C3 C4 C5 179.54(9) . . . . ? C8 C3 C4 C5 -58.84(12) . . . . ? C2 C3 C4 C5 58.04(12) . . . . ? C3 C4 C5 C10 60.64(12) . . . . ? C3 C4 C5 C6 -59.63(13) . . . . ? C10 C5 C6 C1 -61.02(12) . . . . ? C4 C5 C6 C1 59.54(13) . . . . ? C11 C1 C6 C5 -178.76(9) . . . . ? C7 C1 C6 C5 59.10(12) . . . . ? C2 C1 C6 C5 -57.79(12) . . . . ? C11 C1 C7 C9 -179.74(10) . . . . ? C6 C1 C7 C9 -58.57(12) . . . . ? C2 C1 C7 C9 59.54(13) . . . . ? C17 C3 C8 C9 179.44(9) . . . . ? C4 C3 C8 C9 59.00(12) . . . . ? C2 C3 C8 C9 -59.11(12) . . . . ? C3 C8 C9 C10 -61.00(12) . . . . ? C3 C8 C9 C7 59.97(14) . . . . ? C1 C7 C9 C10 60.67(13) . . . . ? C1 C7 C9 C8 -60.19(14) . . . . ? C6 C5 C10 C9 60.38(13) . . . . ? C4 C5 C10 C9 -60.13(13) . . . . ? C8 C9 C10 C5 60.31(12) . . . . ? C7 C9 C10 C5 -60.44(13) . . . . ? C7 C1 C11 C16 -3.10(15) . . . . ? C6 C1 C11 C16 -122.70(11) . . . . ? C2 C1 C11 C16 116.44(11) . . . . ? C7 C1 C11 C12 176.50(10) . . . . ? C6 C1 C11 C12 56.90(13) . . . . ? C2 C1 C11 C12 -63.97(14) . . . . ? C16 C11 C12 O1 -179.98(10) . . . . ? C1 C11 C12 O1 0.41(16) . . . . ? C16 C11 C12 C13 -0.16(16) . . . . ? C1 C11 C12 C13 -179.77(10) . . . . ? O1 C12 C13 C14 179.49(10) . . . . ? C11 C12 C13 C14 -0.32(18) . . . . ? C12 C13 C14 C15 0.50(17) . . . . ? C13 C14 C15 C16 -0.20(17) . . . . ? C13 C14 C15 N1 179.10(10) . . . . ? C14 C15 C16 C11 -0.29(18) . . . . ? N1 C15 C16 C11 -179.59(10) . . . . ? C12 C11 C16 C15 0.45(16) . . . . ? C1 C11 C16 C15 -179.93(10) . . . . ? C8 C3 C17 C22 -3.55(14) . . . . ? C4 C3 C17 C22 115.59(11) . . . . ? C2 C3 C17 C22 -123.41(11) . . . . ? C8 C3 C17 C18 177.27(10) . . . . ? C4 C3 C17 C18 -63.60(13) . . . . ? C2 C3 C17 C18 57.41(13) . . . . ? C22 C17 C18 O4 -177.48(10) . . . . ? C3 C17 C18 O4 1.74(16) . . . . ? C22 C17 C18 C19 2.31(16) . . . . ? C3 C17 C18 C19 -178.47(10) . . . . ? O4 C18 C19 C20 177.48(10) . . . . ? C17 C18 C19 C20 -2.31(18) . . . . ? C18 C19 C20 C21 0.55(17) . . . . ? C19 C20 C21 C22 1.12(17) . . . . ? C19 C20 C21 N2 -179.74(10) . . . . ? C18 C17 C22 C21 -0.66(16) . . . . ? C3 C17 C22 C21 -179.89(10) . . . . ? C20 C21 C22 C17 -1.05(17) . . . . ? N2 C21 C22 C17 179.80(10) . . . . ? C14 C15 N1 O2 7.68(16) . . . . ? C16 C15 N1 O2 -173.00(10) . . . . ? C14 C15 N1 O3 -172.07(11) . . . . ? C16 C15 N1 O3 7.25(16) . . . . ? C20 C21 N2 O5 1.93(16) . . . . ? C22 C21 N2 O5 -178.90(11) . . . . ? C20 C21 N2 O6 -177.79(10) . . . . ? C22 C21 N2 O6 1.38(16) . . . . ? O7 C23 C25 C26 -0.4(3) . . . . ? C24 C23 C25 C26 178.8(3) . . . . ? O7B C23B C25B C26B -5.5(16) . . . . ? C24B C23B C25B C26B 171.5(12) . . . . ?