#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:53:54 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/75/7247594.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_7247594 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 'C22 H22 N2 O6' _chemical_formula_weight 410.41 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens 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 90 _cell_angle_beta 93.490(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.8801(12) _cell_length_b 12.8327(14) _cell_length_c 13.3727(14) _cell_measurement_reflns_used 9910 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 79.52 _cell_measurement_theta_min 3.44 _cell_volume 1863.6(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 0.972 _diffrn_measured_fraction_theta_max 0.949 _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 0.0262 _diffrn_reflns_av_unetI/netI 0.0195 _diffrn_reflns_Laue_measured_fraction_full 0.972 _diffrn_reflns_Laue_measured_fraction_max 0.949 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 22303 _diffrn_reflns_point_group_measured_fraction_full 0.972 _diffrn_reflns_point_group_measured_fraction_max 0.949 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 79.134 _diffrn_reflns_theta_min 4.780 _diffrn_source 'rotating-anode X-ray tube' _exptl_absorpt_coefficient_mu 0.893 _exptl_absorpt_correction_T_max 0.8769 _exptl_absorpt_correction_T_min 0.8070 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS Sheldrick 1996' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.463 _exptl_crystal_description prismatic _exptl_crystal_F_000 864 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.348 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef 0.0088(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 278 _refine_ls_number_reflns 3832 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0350 _refine_ls_R_factor_gt 0.0350 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+1.0597P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0874 _refine_ls_wR_factor_ref 0.0874 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3827 _reflns_number_total 3832 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00775h2.cif _cod_data_source_block 1d _cod_depositor_comments 'Adding full bibliography for 7247591--7247596.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7247594 _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 0.842 _shelx_estimated_absorpt_t_max 0.842 _shelx_res_file ; TITL P21n_a.res in P2(1)/n 1d.res created by SHELXL-2018/3 at 16:14:22 on 22-Dec-2022 REM Old TITL P21n in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.119, Rweak 0.013, Alpha 0.024 REM 1.937 for 179 systematic absences, Orientation as input REM Formula found by SHELXT: C24 O6 CELL 1.54178 10.8801 12.8327 13.3727 90.000 93.490 90.000 ZERR 4.000 0.0012 0.0014 0.0014 0.000 0.004 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 88 88 8 24 OMIT 4 1 12 OMIT -2 0 2 OMIT 1 3 0 OMIT 0 2 0 OMIT 2 3 2 OMIT 1 2 0 TEMP -173.000 SIZE 0.20 0.20 0.20 REM colourless prismatic L.S. 10 ACTA CONF WPDB -2 BOND $H LIST 4 FMAP 2 PLAN 20 WGHT 0.035300 1.059700 EXTI 0.008826 FVAR 1.35556 C1 1 0.265411 0.443296 0.271142 11.00000 0.01032 0.01330 = 0.01284 0.00088 0.00057 0.00050 C2 1 0.344911 0.527667 0.223209 11.00000 0.01095 0.01245 = 0.01168 0.00017 -0.00040 -0.00040 AFIX 23 H2A 2 0.343747 0.592056 0.263918 11.00000 -1.20000 H2B 2 0.431190 0.503122 0.223424 11.00000 -1.20000 AFIX 0 C3 1 0.297636 0.552609 0.114480 11.00000 0.01115 0.01252 = 0.01155 0.00010 -0.00112 -0.00044 C4 1 0.301202 0.449955 0.054033 11.00000 0.01434 0.01414 = 0.01272 -0.00141 -0.00009 0.00001 AFIX 23 H4A 2 0.272494 0.463152 -0.016503 11.00000 -1.20000 H4B 2 0.386880 0.423841 0.054898 11.00000 -1.20000 AFIX 0 C5 1 0.218501 0.367488 0.099430 11.00000 0.01584 0.01298 = 0.01499 -0.00191 -0.00157 -0.00149 AFIX 13 H5 2 0.220336 0.302356 0.058493 11.00000 -1.20000 AFIX 0 C6 1 0.265127 0.343026 0.207191 11.00000 0.01403 0.01177 = 0.01670 0.00050 0.00025 -0.00032 AFIX 23 H6A 2 0.349562 0.314200 0.207677 11.00000 -1.20000 H6B 2 0.211281 0.290122 0.236007 11.00000 -1.20000 AFIX 0 C7 1 0.131585 0.483605 0.269072 11.00000 0.01103 0.01732 = 0.01635 0.00093 0.00155 0.00120 AFIX 23 H7A 2 0.078582 0.430423 0.298438 11.00000 -1.20000 H7B 2 0.128336 0.547583 0.310196 11.00000 -1.20000 AFIX 0 C8 1 0.082899 0.507465 0.161571 11.00000 0.00936 0.01814 = 0.01821 0.00119 -0.00096 0.00102 AFIX 13 H8 2 -0.003814 0.533182 0.162178 11.00000 -1.20000 AFIX 0 C9 1 0.163181 0.591657 0.116891 11.00000 0.01201 0.01449 = 0.01507 0.00034 -0.00190 0.00178 AFIX 23 H9A 2 0.160864 0.655841 0.157808 11.00000 -1.20000 H9B 2 0.130619 0.608561 0.048061 11.00000 -1.20000 AFIX 0 C10 1 0.085896 0.408076 0.098025 11.00000 0.01376 0.01775 = 0.01945 0.00014 -0.00316 -0.00350 AFIX 23 H10A 2 0.031794 0.354466 0.125407 11.00000 -1.20000 H10B 2 0.055443 0.423372 0.028299 11.00000 -1.20000 AFIX 0 C11 1 0.316744 0.421368 0.378348 11.00000 0.01328 0.01148 = 0.01356 0.00078 0.00113 -0.00090 C12 1 0.436678 0.380827 0.399733 11.00000 0.01428 0.01366 = 0.01408 0.00106 0.00265 -0.00011 C13 1 0.481337 0.360765 0.497978 11.00000 0.01599 0.01940 = 0.01677 0.00308 -0.00015 0.00242 AFIX 43 H13 2 0.560938 0.331237 0.509983 11.00000 -1.20000 AFIX 0 C14 1 0.411137 0.383344 0.577953 11.00000 0.02258 0.02061 = 0.01297 0.00266 -0.00028 -0.00074 AFIX 43 H14 2 0.441760 0.370737 0.644906 11.00000 -1.20000 AFIX 0 C15 1 0.295016 0.424826 0.557601 11.00000 0.01999 0.01485 = 0.01429 -0.00008 0.00589 -0.00155 C16 1 0.247312 0.442306 0.460348 11.00000 0.01423 0.01268 = 0.01702 0.00104 0.00312 -0.00042 AFIX 43 H16 2 0.166126 0.468938 0.449494 11.00000 -1.20000 AFIX 0 C17 1 0.378609 0.634765 0.067739 11.00000 0.01222 0.01226 = 0.01221 -0.00026 -0.00016 0.00120 C18 1 0.357490 0.668952 -0.032754 11.00000 0.01394 0.01473 = 0.01319 -0.00127 -0.00206 0.00218 C19 1 0.435145 0.741460 -0.075125 11.00000 0.01781 0.01591 = 0.01114 0.00220 -0.00041 0.00260 AFIX 43 H19 2 0.418506 0.762750 -0.142633 11.00000 -1.20000 AFIX 0 C20 1 0.535583 0.782632 -0.020518 11.00000 0.01578 0.01301 = 0.01535 0.00121 0.00291 0.00047 AFIX 43 H20 2 0.588843 0.831347 -0.049353 11.00000 -1.20000 AFIX 0 C21 1 0.555584 0.750136 0.077842 11.00000 0.01246 0.01329 = 0.01370 -0.00202 -0.00102 -0.00042 C22 1 0.479216 0.678409 0.121517 11.00000 0.01421 0.01423 = 0.01045 -0.00023 0.00003 0.00023 AFIX 43 H22 2 0.496192 0.658873 0.189478 11.00000 -1.20000 AFIX 0 N1 3 0.220315 0.452321 0.640946 11.00000 0.02697 0.01922 = 0.01736 -0.00029 0.00838 -0.00047 N2 3 0.662405 0.787655 0.137066 11.00000 0.01522 0.01393 = 0.01520 -0.00081 0.00051 -0.00202 O1 4 0.509172 0.361228 0.322404 11.00000 0.01250 0.02711 = 0.01380 0.00177 0.00162 0.00591 H1 2 0.581292 0.348384 0.346989 11.00000 -1.50000 O2 4 0.267201 0.444709 0.726647 11.00000 0.04780 0.05557 = 0.01318 0.00055 0.00652 0.01420 O3 4 0.113859 0.482500 0.622147 11.00000 0.02230 0.02663 = 0.02798 -0.00466 0.01111 -0.00060 O4 4 0.259699 0.629066 -0.087354 11.00000 0.01917 0.02407 = 0.01234 0.00364 -0.00644 -0.00452 H4 2 0.254664 0.652480 -0.146170 11.00000 -1.50000 O5 4 0.749107 0.824847 0.092462 11.00000 0.01416 0.02294 = 0.02124 -0.00148 0.00302 -0.00588 O6 4 0.664159 0.780464 0.228990 11.00000 0.02625 0.03111 = 0.01263 -0.00005 -0.00309 -0.01154 HKLF 4 REM P21n_a.res in P2(1)/n REM wR2 = 0.0874, GooF = S = 1.039, Restrained GooF = 1.039 for all data REM R1 = 0.0350 for 3827 Fo > 4sig(Fo) and 0.0350 for all 3832 data REM 278 parameters refined using 0 restraints END WGHT 0.0353 1.0597 REM Highest difference peak 0.348, deepest hole -0.194, 1-sigma level 0.040 Q1 1 0.2932 0.4310 0.3249 11.00000 0.05 0.35 Q2 1 0.2325 0.5746 0.1155 11.00000 0.05 0.30 Q3 1 0.1101 0.4952 0.2158 11.00000 0.05 0.30 Q4 1 0.3178 0.5414 0.1664 11.00000 0.05 0.30 Q5 1 0.3381 0.5960 0.0928 11.00000 0.05 0.29 Q6 1 0.2569 0.4130 0.0787 11.00000 0.05 0.28 Q7 1 0.3049 0.4820 0.2481 11.00000 0.05 0.28 Q8 1 0.1266 0.5482 0.1402 11.00000 0.05 0.27 Q9 1 0.2008 0.4651 0.2688 11.00000 0.05 0.26 Q10 1 0.6047 0.7617 0.1035 11.00000 0.05 0.26 Q11 1 0.5140 0.7161 0.1009 11.00000 0.05 0.25 Q12 1 0.2679 0.3953 0.2396 11.00000 0.05 0.25 Q13 1 0.3884 0.7174 -0.0445 11.00000 0.05 0.23 Q14 1 0.2382 0.3593 0.1553 11.00000 0.05 0.23 Q15 1 0.0862 0.4576 0.1331 11.00000 0.05 0.23 Q16 1 0.2938 0.5022 0.0845 11.00000 0.05 0.23 Q17 1 0.3576 0.6589 0.0220 11.00000 0.05 0.23 Q18 1 0.1526 0.3889 0.0998 11.00000 0.05 0.23 Q19 1 0.3736 0.4062 0.3851 11.00000 0.05 0.23 Q20 1 0.4203 0.6678 0.0948 11.00000 0.05 0.23 ; _shelx_res_checksum 67768 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_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 0.26541(9) 0.44330(8) 0.27114(8) 0.0122(2) Uani 1 1 d . . . . . C2 C 0.34491(9) 0.52767(8) 0.22321(7) 0.0117(2) Uani 1 1 d . . . . . H2A H 0.343747 0.592056 0.263918 0.014 Uiso 1 1 calc R U . . . H2B H 0.431190 0.503122 0.223424 0.014 Uiso 1 1 calc R U . . . C3 C 0.29764(9) 0.55261(8) 0.11448(7) 0.0118(2) Uani 1 1 d . . . . . C4 C 0.30120(10) 0.44995(8) 0.05403(8) 0.0138(2) Uani 1 1 d . . . . . H4A H 0.272494 0.463152 -0.016503 0.017 Uiso 1 1 calc R U . . . H4B H 0.386880 0.423841 0.054898 0.017 Uiso 1 1 calc R U . . . C5 C 0.21850(10) 0.36749(8) 0.09943(8) 0.0147(2) Uani 1 1 d . . . . . H5 H 0.220336 0.302356 0.058493 0.018 Uiso 1 1 calc R U . . . C6 C 0.26513(10) 0.34303(8) 0.20719(8) 0.0142(2) Uani 1 1 d . . . . . H6A H 0.349562 0.314200 0.207677 0.017 Uiso 1 1 calc R U . . . H6B H 0.211281 0.290122 0.236007 0.017 Uiso 1 1 calc R U . . . C7 C 0.13159(9) 0.48361(9) 0.26907(8) 0.0149(2) Uani 1 1 d . . . . . H7A H 0.078582 0.430423 0.298438 0.018 Uiso 1 1 calc R U . . . H7B H 0.128336 0.547583 0.310196 0.018 Uiso 1 1 calc R U . . . C8 C 0.08290(9) 0.50747(9) 0.16157(8) 0.0153(2) Uani 1 1 d . . . . . H8 H -0.003814 0.533182 0.162178 0.018 Uiso 1 1 calc R U . . . C9 C 0.16318(9) 0.59166(8) 0.11689(8) 0.0140(2) Uani 1 1 d . . . . . H9A H 0.160864 0.655841 0.157808 0.017 Uiso 1 1 calc R U . . . H9B H 0.130619 0.608561 0.048061 0.017 Uiso 1 1 calc R U . . . C10 C 0.08590(10) 0.40808(9) 0.09802(8) 0.0172(2) Uani 1 1 d . . . . . H10A H 0.031794 0.354466 0.125407 0.021 Uiso 1 1 calc R U . . . H10B H 0.055443 0.423372 0.028299 0.021 Uiso 1 1 calc R U . . . C11 C 0.31674(9) 0.42137(8) 0.37835(8) 0.0128(2) Uani 1 1 d . . . . . C12 C 0.43668(10) 0.38083(8) 0.39973(8) 0.0139(2) Uani 1 1 d . . . . . C13 C 0.48134(10) 0.36076(9) 0.49798(8) 0.0174(2) Uani 1 1 d . . . . . H13 H 0.560938 0.331237 0.509983 0.021 Uiso 1 1 calc R U . . . C14 C 0.41114(11) 0.38334(9) 0.57795(8) 0.0188(2) Uani 1 1 d . . . . . H14 H 0.441760 0.370737 0.644906 0.023 Uiso 1 1 calc R U . . . C15 C 0.29502(10) 0.42483(9) 0.55760(8) 0.0162(2) Uani 1 1 d . . . . . C16 C 0.24731(10) 0.44231(8) 0.46035(8) 0.0146(2) Uani 1 1 d . . . . . H16 H 0.166126 0.468938 0.449494 0.017 Uiso 1 1 calc R U . . . C17 C 0.37861(9) 0.63477(8) 0.06774(8) 0.0123(2) Uani 1 1 d . . . . . C18 C 0.35749(10) 0.66895(8) -0.03275(8) 0.0141(2) Uani 1 1 d . . . . . C19 C 0.43515(10) 0.74146(8) -0.07512(8) 0.0150(2) Uani 1 1 d . . . . . H19 H 0.418506 0.762750 -0.142633 0.018 Uiso 1 1 calc R U . . . C20 C 0.53558(10) 0.78263(8) -0.02052(8) 0.0146(2) Uani 1 1 d . . . . . H20 H 0.588843 0.831347 -0.049353 0.018 Uiso 1 1 calc R U . . . C21 C 0.55558(9) 0.75014(8) 0.07784(8) 0.0132(2) Uani 1 1 d . . . . . C22 C 0.47922(9) 0.67841(8) 0.12152(8) 0.0130(2) Uani 1 1 d . . . . . H22 H 0.496192 0.658873 0.189478 0.016 Uiso 1 1 calc R U . . . N1 N 0.22032(10) 0.45232(8) 0.64095(7) 0.0209(2) Uani 1 1 d . . . . . N2 N 0.66241(8) 0.78766(7) 0.13707(7) 0.0148(2) Uani 1 1 d . . . . . O1 O 0.50917(7) 0.36123(7) 0.32240(6) 0.01777(19) Uani 1 1 d . . . . . H1 H 0.5813(16) 0.3484(13) 0.3470(12) 0.027 Uiso 1 1 d . U . . . O2 O 0.26720(10) 0.44471(9) 0.72665(7) 0.0387(3) Uani 1 1 d . . . . . O3 O 0.11386(8) 0.48250(7) 0.62215(7) 0.0252(2) Uani 1 1 d . . . . . O4 O 0.25970(7) 0.62907(7) -0.08735(6) 0.01883(19) Uani 1 1 d . . . . . H4 H 0.2547(15) 0.6525(13) -0.1462(13) 0.028 Uiso 1 1 d . U . . . O5 O 0.74911(7) 0.82485(7) 0.09246(6) 0.01937(19) Uani 1 1 d . . . . . O6 O 0.66416(8) 0.78046(7) 0.22899(6) 0.0235(2) 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 0.0103(5) 0.0133(5) 0.0128(5) 0.0009(4) 0.0006(4) 0.0005(4) C2 0.0110(5) 0.0124(5) 0.0117(5) 0.0002(4) -0.0004(4) -0.0004(4) C3 0.0111(5) 0.0125(5) 0.0115(5) 0.0001(4) -0.0011(4) -0.0004(4) C4 0.0143(5) 0.0141(5) 0.0127(5) -0.0014(4) -0.0001(4) 0.0000(4) C5 0.0158(5) 0.0130(5) 0.0150(5) -0.0019(4) -0.0016(4) -0.0015(4) C6 0.0140(5) 0.0118(5) 0.0167(5) 0.0005(4) 0.0003(4) -0.0003(4) C7 0.0110(5) 0.0173(5) 0.0163(5) 0.0009(4) 0.0015(4) 0.0012(4) C8 0.0094(5) 0.0181(5) 0.0182(5) 0.0012(4) -0.0010(4) 0.0010(4) C9 0.0120(5) 0.0145(5) 0.0151(5) 0.0003(4) -0.0019(4) 0.0018(4) C10 0.0138(5) 0.0177(5) 0.0194(5) 0.0001(4) -0.0032(4) -0.0035(4) C11 0.0133(5) 0.0115(5) 0.0136(5) 0.0008(4) 0.0011(4) -0.0009(4) C12 0.0143(5) 0.0137(5) 0.0141(5) 0.0011(4) 0.0027(4) -0.0001(4) C13 0.0160(5) 0.0194(5) 0.0168(5) 0.0031(4) -0.0002(4) 0.0024(4) C14 0.0226(6) 0.0206(6) 0.0130(5) 0.0027(4) -0.0003(4) -0.0007(4) C15 0.0200(5) 0.0149(5) 0.0143(5) -0.0001(4) 0.0059(4) -0.0015(4) C16 0.0142(5) 0.0127(5) 0.0170(5) 0.0010(4) 0.0031(4) -0.0004(4) C17 0.0122(5) 0.0123(5) 0.0122(5) -0.0003(4) -0.0002(4) 0.0012(4) C18 0.0139(5) 0.0147(5) 0.0132(5) -0.0013(4) -0.0021(4) 0.0022(4) C19 0.0178(5) 0.0159(5) 0.0111(5) 0.0022(4) -0.0004(4) 0.0026(4) C20 0.0158(5) 0.0130(5) 0.0154(5) 0.0012(4) 0.0029(4) 0.0005(4) C21 0.0125(5) 0.0133(5) 0.0137(5) -0.0020(4) -0.0010(4) -0.0004(4) C22 0.0142(5) 0.0142(5) 0.0105(5) -0.0002(4) 0.0000(4) 0.0002(4) N1 0.0270(5) 0.0192(5) 0.0174(5) -0.0003(4) 0.0084(4) -0.0005(4) N2 0.0152(4) 0.0139(4) 0.0152(4) -0.0008(3) 0.0005(3) -0.0020(3) O1 0.0125(4) 0.0271(4) 0.0138(4) 0.0018(3) 0.0016(3) 0.0059(3) O2 0.0478(6) 0.0556(7) 0.0132(4) 0.0005(4) 0.0065(4) 0.0142(5) O3 0.0223(4) 0.0266(5) 0.0280(5) -0.0047(4) 0.0111(3) -0.0006(4) O4 0.0192(4) 0.0241(4) 0.0123(4) 0.0036(3) -0.0064(3) -0.0045(3) O5 0.0142(4) 0.0229(4) 0.0212(4) -0.0015(3) 0.0030(3) -0.0059(3) O6 0.0263(4) 0.0311(5) 0.0126(4) 0.0000(3) -0.0031(3) -0.0115(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 111.58(8) . . ? C11 C1 C6 110.68(8) . . ? C7 C1 C6 107.40(8) . . ? C11 C1 C2 109.55(8) . . ? C7 C1 C2 107.95(8) . . ? C6 C1 C2 109.60(8) . . ? C3 C2 C1 111.82(8) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C17 C3 C2 111.08(8) . . ? C17 C3 C4 109.85(8) . . ? C2 C3 C4 107.31(8) . . ? C17 C3 C9 110.69(8) . . ? C2 C3 C9 107.94(8) . . ? C4 C3 C9 109.89(8) . . ? C5 C4 C3 110.23(8) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C10 109.81(9) . . ? C6 C5 C4 110.15(8) . . ? C10 C5 C4 109.53(9) . . ? C6 C5 H5 109.1 . . ? C10 C5 H5 109.1 . . ? C4 C5 H5 109.1 . . ? C5 C6 C1 109.86(8) . . ? C5 C6 H6A 109.7 . . ? C1 C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? C1 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C8 C7 C1 110.83(8) . . ? C8 C7 H7A 109.5 . . ? C1 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C7 C8 C9 109.50(8) . . ? C7 C8 C10 109.62(9) . . ? C9 C8 C10 109.77(9) . . ? C7 C8 H8 109.3 . . ? C9 C8 H8 109.3 . . ? C10 C8 H8 109.3 . . ? C8 C9 C3 109.96(8) . . ? C8 C9 H9A 109.7 . . ? C3 C9 H9A 109.7 . . ? C8 C9 H9B 109.7 . . ? C3 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C5 C10 C8 109.11(8) . . ? C5 C10 H10A 109.9 . . ? C8 C10 H10A 109.9 . . ? C5 C10 H10B 109.9 . . ? C8 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? C16 C11 C12 116.61(10) . . ? C16 C11 C1 121.06(9) . . ? C12 C11 C1 122.32(9) . . ? O1 C12 C13 119.73(10) . . ? O1 C12 C11 118.90(9) . . ? C13 C12 C11 121.37(10) . . ? C14 C13 C12 120.81(10) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C15 118.02(10) . . ? C13 C14 H14 121.0 . . ? C15 C14 H14 121.0 . . ? C14 C15 C16 122.10(10) . . ? C14 C15 N1 119.11(10) . . ? C16 C15 N1 118.78(10) . . ? C15 C16 C11 121.04(10) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C22 C17 C18 116.25(10) . . ? C22 C17 C3 121.37(9) . . ? C18 C17 C3 122.37(9) . . ? O4 C18 C19 120.47(9) . . ? O4 C18 C17 118.07(10) . . ? C19 C18 C17 121.47(10) . . ? C20 C19 C18 121.18(10) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 117.42(10) . . ? C19 C20 H20 121.3 . . ? C21 C20 H20 121.3 . . ? C20 C21 C22 122.31(10) . . ? C20 C21 N2 119.60(9) . . ? C22 C21 N2 118.03(9) . . ? C17 C22 C21 121.37(9) . . ? C17 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? O2 N1 O3 123.12(10) . . ? O2 N1 C15 118.23(10) . . ? O3 N1 C15 118.65(10) . . ? O6 N2 O5 122.83(9) . . ? O6 N2 C21 118.95(9) . . ? O5 N2 C21 118.22(9) . . ? C12 O1 H1 107.8(11) . . ? C18 O4 H4 112.0(11) . . ? 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 1.5326(14) . ? C1 C7 1.5439(14) . ? C1 C6 1.5449(14) . ? C1 C2 1.5488(14) . ? C2 C3 1.5460(13) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C17 1.5315(14) . ? C3 C4 1.5473(14) . ? C3 C9 1.5485(14) . ? C4 C5 1.5377(15) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5309(14) . ? C5 C10 1.5329(15) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5324(15) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.5332(15) . ? C8 C10 1.5341(15) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C16 1.3950(15) . ? C11 C12 1.4177(15) . ? C12 O1 1.3616(13) . ? C12 C13 1.3967(15) . ? C13 C14 1.3822(16) . ? C13 H13 0.9500 . ? C14 C15 1.3827(16) . ? C14 H14 0.9500 . ? C15 C16 1.3889(15) . ? C15 N1 1.4620(14) . ? C16 H16 0.9500 . ? C17 C22 1.3904(14) . ? C17 C18 1.4190(14) . ? C18 O4 1.3537(13) . ? C18 C19 1.3996(16) . ? C19 C20 1.3818(15) . ? C19 H19 0.9500 . ? C20 C21 1.3844(15) . ? C20 H20 0.9500 . ? C21 C22 1.3921(15) . ? C21 N2 1.4484(13) . ? C22 H22 0.9500 . ? N1 O2 1.2296(14) . ? N1 O3 1.2326(14) . ? N2 O6 1.2317(12) . ? N2 O5 1.2418(12) . ? O1 H1 0.848(17) . ? O4 H4 0.841(17) . ? 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 179.71(8) . . . . ? C7 C1 C2 C3 -58.59(11) . . . . ? C6 C1 C2 C3 58.09(11) . . . . ? C1 C2 C3 C17 -179.03(8) . . . . ? C1 C2 C3 C4 -58.95(10) . . . . ? C1 C2 C3 C9 59.44(11) . . . . ? C17 C3 C4 C5 -179.10(8) . . . . ? C2 C3 C4 C5 60.03(10) . . . . ? C9 C3 C4 C5 -57.09(11) . . . . ? C3 C4 C5 C6 -61.61(11) . . . . ? C3 C4 C5 C10 59.27(11) . . . . ? C10 C5 C6 C1 -61.58(11) . . . . ? C4 C5 C6 C1 59.12(11) . . . . ? C11 C1 C6 C5 -177.71(8) . . . . ? C7 C1 C6 C5 60.26(11) . . . . ? C2 C1 C6 C5 -56.77(11) . . . . ? C11 C1 C7 C8 178.69(9) . . . . ? C6 C1 C7 C8 -59.84(11) . . . . ? C2 C1 C7 C8 58.27(11) . . . . ? C1 C7 C8 C9 -60.44(11) . . . . ? C1 C7 C8 C10 60.03(11) . . . . ? C7 C8 C9 C3 60.81(11) . . . . ? C10 C8 C9 C3 -59.57(11) . . . . ? C17 C3 C9 C8 178.65(8) . . . . ? C2 C3 C9 C8 -59.58(11) . . . . ? C4 C3 C9 C8 57.15(11) . . . . ? C6 C5 C10 C8 59.97(11) . . . . ? C4 C5 C10 C8 -61.11(11) . . . . ? C7 C8 C10 C5 -58.83(11) . . . . ? C9 C8 C10 C5 61.48(11) . . . . ? C7 C1 C11 C16 -2.93(14) . . . . ? C6 C1 C11 C16 -122.48(10) . . . . ? C2 C1 C11 C16 116.55(11) . . . . ? C7 C1 C11 C12 178.14(10) . . . . ? C6 C1 C11 C12 58.59(13) . . . . ? C2 C1 C11 C12 -62.38(13) . . . . ? C16 C11 C12 O1 -178.58(9) . . . . ? C1 C11 C12 O1 0.40(15) . . . . ? C16 C11 C12 C13 1.46(16) . . . . ? C1 C11 C12 C13 -179.57(10) . . . . ? O1 C12 C13 C14 177.77(10) . . . . ? C11 C12 C13 C14 -2.27(17) . . . . ? C12 C13 C14 C15 0.94(17) . . . . ? C13 C14 C15 C16 1.13(17) . . . . ? C13 C14 C15 N1 -178.18(10) . . . . ? C14 C15 C16 C11 -1.93(17) . . . . ? N1 C15 C16 C11 177.39(10) . . . . ? C12 C11 C16 C15 0.59(16) . . . . ? C1 C11 C16 C15 -178.40(10) . . . . ? C2 C3 C17 C22 -0.68(13) . . . . ? C4 C3 C17 C22 -119.25(10) . . . . ? C9 C3 C17 C22 119.22(10) . . . . ? C2 C3 C17 C18 177.87(9) . . . . ? C4 C3 C17 C18 59.31(12) . . . . ? C9 C3 C17 C18 -62.22(12) . . . . ? C22 C17 C18 O4 -179.36(9) . . . . ? C3 C17 C18 O4 2.01(15) . . . . ? C22 C17 C18 C19 0.88(15) . . . . ? C3 C17 C18 C19 -177.75(10) . . . . ? O4 C18 C19 C20 -179.77(10) . . . . ? C17 C18 C19 C20 -0.02(16) . . . . ? C18 C19 C20 C21 -0.61(16) . . . . ? C19 C20 C21 C22 0.37(16) . . . . ? C19 C20 C21 N2 177.48(9) . . . . ? C18 C17 C22 C21 -1.12(15) . . . . ? C3 C17 C22 C21 177.52(9) . . . . ? C20 C21 C22 C17 0.53(16) . . . . ? N2 C21 C22 C17 -176.63(9) . . . . ? C14 C15 N1 O2 5.31(16) . . . . ? C16 C15 N1 O2 -174.03(11) . . . . ? C14 C15 N1 O3 -175.08(10) . . . . ? C16 C15 N1 O3 5.58(15) . . . . ? C20 C21 N2 O6 162.02(10) . . . . ? C22 C21 N2 O6 -20.74(15) . . . . ? C20 C21 N2 O5 -18.71(14) . . . . ? C22 C21 N2 O5 158.52(10) . . . . ?