#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:12:07 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257326 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557873.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_1557873 loop_ _publ_author_name 'Yan, Chenting' 'Takeshita, Masato' 'Nakatsuji, Jun-ya' 'Kurosaki, Akihiro' 'Sato, Kaoko' 'Shang, Rong' 'Nakamoto, Masaaki' 'Yamamoto, Yohsuke' 'Adachi, Yohei' 'Furukawa, Ko' 'Kishi, Ryohei' 'Nakano, Masayoshi' _publ_section_title ; Synthesis and properties of hypervalent electron-rich pentacoordinate nitrogen compounds ; _journal_issue 19 _journal_name_full 'Chemical Science' _journal_page_first 5082 _journal_page_last 5088 _journal_paper_doi 10.1039/D0SC00002G _journal_volume 11 _journal_year 2020 _chemical_formula_sum 'C28 H31 N O6' _chemical_formula_weight 477.54 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-03-07 deposited with the CCDC. 2020-04-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.843(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.3036(6) _cell_length_b 18.9257(11) _cell_length_c 13.0352(7) _cell_measurement_reflns_used 9281 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.05 _cell_measurement_theta_min 2.27 _cell_volume 2532.8(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_unetI/netI 0.0370 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 26160 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.482 _diffrn_reflns_theta_min 3.137 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1016 _exptl_crystal_size_max 0.420 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.240 _refine_diff_density_max 0.251 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.043 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.597 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 323 _refine_ls_number_reflns 5792 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.597 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0510 _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^)+(0.1046P)^2^+8.4575P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1285 _refine_ls_wR_factor_ref 0.1593 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4146 _reflns_number_total 5792 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00002g2.cif _cod_data_source_block ak246_a _cod_depositor_comments ;Adding full bibliography for 1557869--1557876.cif. Adding full bibliography for 1557869--1557876.cif. ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557873 _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 0.964 _shelx_estimated_absorpt_t_max 0.979 _shelx_res_file ; TITL ak246_a.res in P2(1)/c ak246_a.res created by SHELXL-2018/3 at 11:58:35 on 07-Mar-2020 CELL 0.71075 10.3036 18.9257 13.0352 90.000 94.843 90.000 ZERR 4.000 0.0006 0.0011 0.0007 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 112 124 4 24 LIST 4 TEMP -100.0 SIZE 0.30 0.42 0.24 ACTA L.S. 20 FMAP 2 PLAN -5 0 0.00 HTAB BOND $H CONF WGHT 0.104600 8.457500 FVAR 0.41240 O1 4 0.871578 0.326844 0.285639 11.00000 0.02218 0.03038 = 0.03520 -0.00241 -0.00085 -0.00375 N1 3 0.529170 0.254032 0.304459 11.00000 0.01789 0.02704 = 0.03288 -0.00629 -0.00297 0.00171 C1 1 0.623742 0.201066 0.296294 11.00000 0.01875 0.02677 = 0.02462 -0.00274 -0.00137 0.00092 O2 4 0.715649 0.313108 0.156121 11.00000 0.03624 0.03022 = 0.03205 0.00586 -0.00770 -0.00551 C2 1 0.749481 0.219015 0.271274 11.00000 0.02047 0.02606 = 0.02377 -0.00192 -0.00138 -0.00083 C3 1 0.846033 0.167963 0.269835 11.00000 0.01791 0.03295 = 0.02579 -0.00014 -0.00042 0.00132 AFIX 43 H3 2 0.931989 0.182080 0.258024 11.00000 -1.20000 AFIX 0 O3 4 0.452291 0.141257 0.441998 11.00000 0.03186 0.03740 = 0.04094 -0.00750 0.01256 -0.00944 C4 1 0.820571 0.096683 0.285198 11.00000 0.02467 0.02790 = 0.02629 0.00033 -0.00061 0.00339 O4 4 0.417363 0.053167 0.329373 11.00000 0.05543 0.06144 = 0.07943 -0.03428 0.03105 -0.03541 O5 4 0.697099 0.488625 0.536499 11.00000 0.05689 0.02643 = 0.04655 -0.00845 -0.00461 -0.00551 C5 1 0.694709 0.078937 0.306130 11.00000 0.02722 0.02580 = 0.02989 0.00065 0.00037 -0.00031 AFIX 43 H5 2 0.673061 0.030550 0.313923 11.00000 -1.20000 AFIX 0 C6 1 0.599389 0.130008 0.316017 11.00000 0.02086 0.02891 = 0.02835 -0.00208 0.00099 -0.00263 O6 4 0.027824 0.253444 0.105992 11.00000 0.01964 0.05817 = 0.02968 -0.00269 -0.00365 0.00018 C7 1 0.930172 0.042173 0.281622 11.00000 0.02685 0.02873 = 0.05093 -0.00050 -0.00234 0.00729 C9 1 0.992019 0.048149 0.179089 11.00000 0.04521 0.04961 = 0.08247 0.00216 0.02983 0.01634 AFIX 137 H9A 2 0.924938 0.041327 0.122052 11.00000 -1.50000 H9B 2 1.059477 0.011895 0.175948 11.00000 -1.50000 H9C 2 1.031186 0.095049 0.173706 11.00000 -1.50000 AFIX 0 C8 1 1.033492 0.058608 0.369935 11.00000 0.05501 0.05269 = 0.09790 -0.01182 -0.03922 0.02378 AFIX 137 H8A 2 1.105551 0.024919 0.368537 11.00000 -1.50000 H8B 2 0.994637 0.054699 0.435778 11.00000 -1.50000 H8C 2 1.066362 0.106716 0.361966 11.00000 -1.50000 AFIX 0 C10 1 0.881953 -0.032948 0.291389 11.00000 0.04363 0.02969 = 0.07853 0.00315 0.00616 0.01020 AFIX 137 H10A 2 0.812647 -0.042338 0.236898 11.00000 -1.50000 H10B 2 0.847878 -0.039193 0.358755 11.00000 -1.50000 H10C 2 0.954141 -0.065909 0.284834 11.00000 -1.50000 AFIX 0 C11 1 0.565681 0.315813 0.362479 11.00000 0.01588 0.02676 = 0.02861 -0.00353 0.00121 -0.00002 C12 1 0.546476 0.382773 0.321549 11.00000 0.02699 0.03116 = 0.02948 0.00183 -0.00419 0.00233 AFIX 43 H12 2 0.503860 0.388037 0.254468 11.00000 -1.20000 AFIX 0 C13 1 0.588302 0.442336 0.376665 11.00000 0.03132 0.02401 = 0.03723 0.00281 0.00325 0.00260 AFIX 43 H13 2 0.574441 0.488078 0.347781 11.00000 -1.20000 AFIX 0 C14 1 0.650542 0.434375 0.474342 11.00000 0.02823 0.02506 = 0.03551 -0.00593 0.00207 -0.00283 C15 1 0.667990 0.367472 0.517269 11.00000 0.03048 0.03103 = 0.02846 -0.00268 -0.00228 -0.00006 AFIX 43 H15 2 0.709391 0.362254 0.584768 11.00000 -1.20000 AFIX 0 C16 1 0.624984 0.308415 0.461583 11.00000 0.02311 0.02374 = 0.02940 0.00070 0.00249 0.00080 AFIX 43 H16 2 0.636079 0.262738 0.491253 11.00000 -1.20000 AFIX 0 C17 1 0.701110 0.556585 0.491198 11.00000 0.05209 0.02646 = 0.05785 -0.00632 0.01415 -0.00813 AFIX 137 H17A 2 0.747489 0.553934 0.428696 11.00000 -1.50000 H17B 2 0.746536 0.589400 0.540079 11.00000 -1.50000 H17C 2 0.612081 0.573411 0.473497 11.00000 -1.50000 AFIX 0 C18 1 0.402724 0.249147 0.253429 11.00000 0.01880 0.02620 = 0.02533 0.00011 0.00022 -0.00062 C19 1 0.297195 0.278862 0.298497 11.00000 0.02341 0.03892 = 0.02507 -0.00881 0.00103 0.00113 AFIX 43 H19 2 0.310390 0.299070 0.365276 11.00000 -1.20000 AFIX 0 C20 1 0.174235 0.279380 0.247781 11.00000 0.02061 0.03878 = 0.02988 -0.00486 0.00308 0.00201 AFIX 43 H20 2 0.103871 0.300387 0.279277 11.00000 -1.20000 AFIX 0 C21 1 0.153230 0.249294 0.150946 11.00000 0.01902 0.03067 = 0.02676 0.00199 -0.00258 -0.00212 C22 1 0.255968 0.217616 0.106393 11.00000 0.02744 0.03722 = 0.02381 -0.00614 -0.00037 0.00066 AFIX 43 H22 2 0.241540 0.195406 0.041069 11.00000 -1.20000 AFIX 0 C23 1 0.380335 0.218328 0.157334 11.00000 0.02293 0.03511 = 0.02894 -0.00470 0.00323 0.00301 AFIX 43 H23 2 0.450659 0.197391 0.125704 11.00000 -1.20000 AFIX 0 C24 1 0.003021 0.227442 0.003540 11.00000 0.03223 0.06432 = 0.03260 -0.00343 -0.00898 -0.00202 AFIX 137 H24A 2 -0.089158 0.234254 -0.019442 11.00000 -1.50000 H24B 2 0.024180 0.176991 0.001960 11.00000 -1.50000 H24C 2 0.056995 0.253210 -0.042307 11.00000 -1.50000 AFIX 0 C25 1 0.750046 0.381755 0.117612 11.00000 0.05508 0.03708 = 0.04467 0.01578 -0.00768 -0.01048 AFIX 137 H25A 2 0.841345 0.381341 0.101775 11.00000 -1.50000 H25B 2 0.737924 0.417768 0.169974 11.00000 -1.50000 H25C 2 0.694157 0.392630 0.055017 11.00000 -1.50000 AFIX 0 C26 1 0.786179 0.292449 0.241891 11.00000 0.01987 0.02851 = 0.02510 -0.00149 0.00184 0.00123 C27 1 0.478039 0.103976 0.359253 11.00000 0.02677 0.03194 = 0.04051 -0.00424 0.00496 -0.00604 C28 1 0.347954 0.115208 0.498853 11.00000 0.04831 0.05769 = 0.05884 -0.01026 0.02916 -0.01630 AFIX 137 H28A 2 0.264642 0.121643 0.457809 11.00000 -1.50000 H28B 2 0.346776 0.141418 0.563607 11.00000 -1.50000 H28C 2 0.361590 0.064871 0.513754 11.00000 -1.50000 AFIX 0 HKLF 4 REM ak246_a.res in P2(1)/c REM wR2 = 0.1593, GooF = S = 0.597, Restrained GooF = 0.597 for all data REM R1 = 0.0510 for 4146 Fo > 4sig(Fo) and 0.0769 for all 5792 data REM 323 parameters refined using 0 restraints END WGHT 0.0512 1.0714 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, y+1/2, -z+1/2 HTAB C13 O4_$1 EQIV $2 x, -y+1/2, z+1/2 HTAB C16 O2_$2 EQIV $3 x-1, y, z HTAB C20 O1_$3 REM Highest difference peak 0.251, deepest hole -0.215, 1-sigma level 0.043 Q1 1 0.6022 0.1595 0.2775 11.00000 0.05 0.25 Q2 1 0.4046 0.0786 0.2522 11.00000 0.05 0.22 Q3 1 0.3988 0.2538 0.1891 11.00000 0.05 0.22 Q4 1 0.6802 0.3974 0.4823 11.00000 0.05 0.21 Q5 1 0.2913 0.1490 0.4271 11.00000 0.05 0.21 ; _shelx_res_checksum 5534 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O1 O 0.87158(13) 0.32684(8) 0.28564(11) 0.0294(3) Uani 1 1 d . . . . . N1 N 0.52917(15) 0.25403(9) 0.30446(13) 0.0262(4) Uani 1 1 d . . . . . C1 C 0.62374(18) 0.20107(10) 0.29629(15) 0.0236(4) Uani 1 1 d . . . . . O2 O 0.71565(15) 0.31311(8) 0.15612(12) 0.0334(4) Uani 1 1 d . . . . . C2 C 0.74948(18) 0.21901(10) 0.27127(15) 0.0236(4) Uani 1 1 d . . . . . C3 C 0.84603(18) 0.16796(11) 0.26984(15) 0.0257(4) Uani 1 1 d . . . . . H3 H 0.931989 0.182080 0.258024 0.031 Uiso 1 1 calc R U . . . O3 O 0.45229(15) 0.14126(8) 0.44200(12) 0.0362(4) Uani 1 1 d . . . . . C4 C 0.82057(19) 0.09668(11) 0.28520(15) 0.0264(4) Uani 1 1 d . . . . . O4 O 0.4174(2) 0.05317(11) 0.32937(18) 0.0640(6) Uani 1 1 d . . . . . O5 O 0.69710(18) 0.48862(9) 0.53650(14) 0.0438(4) Uani 1 1 d . . . . . C5 C 0.69471(19) 0.07894(11) 0.30613(16) 0.0278(4) Uani 1 1 d . . . . . H5 H 0.673061 0.030550 0.313923 0.033 Uiso 1 1 calc R U . . . C6 C 0.59939(18) 0.13001(11) 0.31602(15) 0.0261(4) Uani 1 1 d . . . . . O6 O 0.02782(14) 0.25344(9) 0.10599(12) 0.0362(4) Uani 1 1 d . . . . . C7 C 0.9302(2) 0.04217(12) 0.28162(19) 0.0358(5) Uani 1 1 d . . . . . C9 C 0.9920(3) 0.04815(16) 0.1791(3) 0.0577(8) Uani 1 1 d . . . . . H9A H 0.924938 0.041327 0.122052 0.087 Uiso 1 1 calc R U . . . H9B H 1.059477 0.011895 0.175948 0.087 Uiso 1 1 calc R U . . . H9C H 1.031186 0.095049 0.173706 0.087 Uiso 1 1 calc R U . . . C8 C 1.0335(3) 0.05861(17) 0.3699(3) 0.0711(11) Uani 1 1 d . . . . . H8A H 1.105551 0.024919 0.368537 0.107 Uiso 1 1 calc R U . . . H8B H 0.994637 0.054699 0.435778 0.107 Uiso 1 1 calc R U . . . H8C H 1.066362 0.106716 0.361966 0.107 Uiso 1 1 calc R U . . . C10 C 0.8820(3) -0.03295(13) 0.2914(3) 0.0506(7) Uani 1 1 d . . . . . H10A H 0.812647 -0.042338 0.236898 0.076 Uiso 1 1 calc R U . . . H10B H 0.847878 -0.039193 0.358755 0.076 Uiso 1 1 calc R U . . . H10C H 0.954141 -0.065909 0.284834 0.076 Uiso 1 1 calc R U . . . C11 C 0.56568(17) 0.31581(10) 0.36248(15) 0.0238(4) Uani 1 1 d . . . . . C12 C 0.5465(2) 0.38277(11) 0.32155(16) 0.0296(4) Uani 1 1 d . . . . . H12 H 0.503860 0.388037 0.254468 0.036 Uiso 1 1 calc R U . . . C13 C 0.5883(2) 0.44234(11) 0.37666(17) 0.0308(5) Uani 1 1 d . . . . . H13 H 0.574441 0.488078 0.347781 0.037 Uiso 1 1 calc R U . . . C14 C 0.6505(2) 0.43438(11) 0.47434(17) 0.0296(4) Uani 1 1 d . . . . . C15 C 0.6680(2) 0.36747(11) 0.51727(16) 0.0303(4) Uani 1 1 d . . . . . H15 H 0.709391 0.362254 0.584768 0.036 Uiso 1 1 calc R U . . . C16 C 0.62498(18) 0.30842(11) 0.46158(15) 0.0254(4) Uani 1 1 d . . . . . H16 H 0.636079 0.262738 0.491253 0.030 Uiso 1 1 calc R U . . . C17 C 0.7011(3) 0.55659(12) 0.4912(2) 0.0449(6) Uani 1 1 d . . . . . H17A H 0.747489 0.553934 0.428696 0.067 Uiso 1 1 calc R U . . . H17B H 0.746536 0.589400 0.540079 0.067 Uiso 1 1 calc R U . . . H17C H 0.612081 0.573411 0.473497 0.067 Uiso 1 1 calc R U . . . C18 C 0.40272(18) 0.24915(10) 0.25343(15) 0.0235(4) Uani 1 1 d . . . . . C19 C 0.29719(19) 0.27886(12) 0.29850(16) 0.0292(4) Uani 1 1 d . . . . . H19 H 0.310390 0.299070 0.365276 0.035 Uiso 1 1 calc R U . . . C20 C 0.17423(19) 0.27938(12) 0.24778(16) 0.0297(4) Uani 1 1 d . . . . . H20 H 0.103871 0.300387 0.279277 0.036 Uiso 1 1 calc R U . . . C21 C 0.15323(18) 0.24929(11) 0.15095(15) 0.0257(4) Uani 1 1 d . . . . . C22 C 0.2560(2) 0.21762(12) 0.10639(16) 0.0296(4) Uani 1 1 d . . . . . H22 H 0.241540 0.195406 0.041069 0.036 Uiso 1 1 calc R U . . . C23 C 0.38033(19) 0.21833(11) 0.15733(16) 0.0289(4) Uani 1 1 d . . . . . H23 H 0.450659 0.197391 0.125704 0.035 Uiso 1 1 calc R U . . . C24 C 0.0030(2) 0.22744(16) 0.00354(19) 0.0437(6) Uani 1 1 d . . . . . H24A H -0.089158 0.234254 -0.019442 0.066 Uiso 1 1 calc R U . . . H24B H 0.024180 0.176991 0.001960 0.066 Uiso 1 1 calc R U . . . H24C H 0.056995 0.253210 -0.042307 0.066 Uiso 1 1 calc R U . . . C25 C 0.7500(3) 0.38176(13) 0.1176(2) 0.0463(6) Uani 1 1 d . . . . . H25A H 0.841345 0.381341 0.101775 0.069 Uiso 1 1 calc R U . . . H25B H 0.737924 0.417768 0.169974 0.069 Uiso 1 1 calc R U . . . H25C H 0.694157 0.392630 0.055017 0.069 Uiso 1 1 calc R U . . . C26 C 0.78618(18) 0.29245(11) 0.24189(15) 0.0245(4) Uani 1 1 d . . . . . C27 C 0.4780(2) 0.10398(12) 0.35925(18) 0.0330(5) Uani 1 1 d . . . . . C28 C 0.3480(3) 0.11521(16) 0.4989(2) 0.0535(7) Uani 1 1 d . . . . . H28A H 0.264642 0.121643 0.457809 0.080 Uiso 1 1 calc R U . . . H28B H 0.346776 0.141418 0.563607 0.080 Uiso 1 1 calc R U . . . H28C H 0.361590 0.064871 0.513754 0.080 Uiso 1 1 calc R U . . . 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 O1 0.0222(7) 0.0304(8) 0.0352(8) -0.0024(6) -0.0008(6) -0.0037(6) N1 0.0179(8) 0.0270(9) 0.0329(9) -0.0063(7) -0.0030(6) 0.0017(6) C1 0.0188(8) 0.0268(10) 0.0246(9) -0.0027(7) -0.0014(7) 0.0009(7) O2 0.0362(8) 0.0302(8) 0.0321(8) 0.0059(6) -0.0077(6) -0.0055(6) C2 0.0205(9) 0.0261(10) 0.0238(9) -0.0019(7) -0.0014(7) -0.0008(7) C3 0.0179(9) 0.0330(11) 0.0258(10) -0.0001(8) -0.0004(7) 0.0013(7) O3 0.0319(8) 0.0374(9) 0.0409(9) -0.0075(7) 0.0126(7) -0.0094(6) C4 0.0247(9) 0.0279(10) 0.0263(10) 0.0003(8) -0.0006(7) 0.0034(8) O4 0.0554(12) 0.0614(13) 0.0794(15) -0.0343(11) 0.0311(11) -0.0354(10) O5 0.0569(11) 0.0264(8) 0.0466(10) -0.0084(7) -0.0046(8) -0.0055(7) C5 0.0272(10) 0.0258(10) 0.0299(10) 0.0007(8) 0.0004(8) -0.0003(8) C6 0.0209(9) 0.0289(10) 0.0283(10) -0.0021(8) 0.0010(7) -0.0026(7) O6 0.0196(7) 0.0582(11) 0.0297(8) -0.0027(7) -0.0036(6) 0.0002(7) C7 0.0268(10) 0.0287(11) 0.0509(14) -0.0005(10) -0.0023(9) 0.0073(8) C9 0.0452(15) 0.0496(16) 0.082(2) 0.0022(15) 0.0298(15) 0.0163(12) C8 0.0550(18) 0.0527(18) 0.098(3) -0.0118(17) -0.0392(18) 0.0238(14) C10 0.0436(14) 0.0297(13) 0.079(2) 0.0032(12) 0.0062(13) 0.0102(10) C11 0.0159(8) 0.0268(10) 0.0286(10) -0.0035(8) 0.0012(7) 0.0000(7) C12 0.0270(10) 0.0312(11) 0.0295(10) 0.0018(8) -0.0042(8) 0.0023(8) C13 0.0313(11) 0.0240(10) 0.0372(12) 0.0028(8) 0.0032(9) 0.0026(8) C14 0.0282(10) 0.0251(10) 0.0355(11) -0.0059(8) 0.0021(8) -0.0028(8) C15 0.0305(10) 0.0310(11) 0.0285(10) -0.0027(8) -0.0023(8) -0.0001(8) C16 0.0231(9) 0.0237(10) 0.0294(10) 0.0007(8) 0.0025(8) 0.0008(7) C17 0.0521(15) 0.0265(12) 0.0579(16) -0.0063(11) 0.0141(12) -0.0081(10) C18 0.0188(9) 0.0262(10) 0.0253(9) 0.0001(7) 0.0002(7) -0.0006(7) C19 0.0234(9) 0.0389(12) 0.0251(10) -0.0088(8) 0.0010(8) 0.0011(8) C20 0.0206(9) 0.0388(12) 0.0299(11) -0.0049(9) 0.0031(8) 0.0020(8) C21 0.0190(9) 0.0307(10) 0.0268(10) 0.0020(8) -0.0026(7) -0.0021(7) C22 0.0274(10) 0.0372(12) 0.0238(10) -0.0061(8) -0.0004(8) 0.0007(8) C23 0.0229(9) 0.0351(11) 0.0289(10) -0.0047(8) 0.0032(8) 0.0030(8) C24 0.0322(11) 0.0643(17) 0.0326(12) -0.0034(11) -0.0090(9) -0.0020(11) C25 0.0551(15) 0.0371(13) 0.0447(14) 0.0158(11) -0.0077(12) -0.0105(11) C26 0.0199(9) 0.0285(10) 0.0251(9) -0.0015(8) 0.0018(7) 0.0012(7) C27 0.0268(10) 0.0319(11) 0.0405(12) -0.0042(9) 0.0050(9) -0.0060(8) C28 0.0483(15) 0.0577(17) 0.0588(17) -0.0103(13) 0.0292(13) -0.0163(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C1 N1 C18 122.24(16) . . ? C1 N1 C11 118.07(15) . . ? C18 N1 C11 119.62(16) . . ? C6 C1 C2 117.36(17) . . ? C6 C1 N1 122.38(17) . . ? C2 C1 N1 120.21(18) . . ? C26 O2 C25 114.83(17) . . ? C3 C2 C1 120.74(19) . . ? C3 C2 C26 116.46(17) . . ? C1 C2 C26 122.78(17) . . ? C2 C3 C4 121.91(18) . . ? C2 C3 H3 119.0 . . ? C4 C3 H3 119.0 . . ? C27 O3 C28 116.24(18) . . ? C5 C4 C3 116.94(18) . . ? C5 C4 C7 123.07(19) . . ? C3 C4 C7 119.97(18) . . ? C14 O5 C17 117.06(19) . . ? C4 C5 C6 121.89(19) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C1 120.85(18) . . ? C5 C6 C27 115.12(18) . . ? C1 C6 C27 123.71(18) . . ? C21 O6 C24 117.84(17) . . ? C10 C7 C8 109.8(2) . . ? C10 C7 C9 107.8(2) . . ? C8 C7 C9 109.1(3) . . ? C10 C7 C4 112.41(19) . . ? C8 C7 C4 107.9(2) . . ? C9 C7 C4 109.78(19) . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C16 119.26(18) . . ? C12 C11 N1 121.61(18) . . ? C16 C11 N1 119.11(18) . . ? C11 C12 C13 121.16(19) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 119.20(19) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? O5 C14 C13 125.1(2) . . ? O5 C14 C15 114.70(19) . . ? C13 C14 C15 120.23(19) . . ? C16 C15 C14 119.96(19) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.16(19) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? O5 C17 H17A 109.5 . . ? O5 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O5 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 118.31(18) . . ? C23 C18 N1 121.99(17) . . ? C19 C18 N1 119.64(17) . . ? C20 C19 C18 121.17(19) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 120.04(19) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? O6 C21 C20 115.71(18) . . ? O6 C21 C22 124.72(18) . . ? C20 C21 C22 119.58(18) . . ? C21 C22 C23 120.04(19) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C18 C23 C22 120.81(19) . . ? C18 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O2 C25 H25A 109.5 . . ? O2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O1 C26 O2 124.27(19) . . ? O1 C26 C2 124.94(18) . . ? O2 C26 C2 110.69(16) . . ? O4 C27 O3 123.7(2) . . ? O4 C27 C6 125.0(2) . . ? O3 C27 C6 111.08(17) . . ? O3 C28 H28A 109.5 . . ? O3 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O3 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 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 O1 C26 1.199(2) . ? N1 C1 1.408(2) . ? N1 C18 1.415(2) . ? N1 C11 1.426(2) . ? C1 C6 1.396(3) . ? C1 C2 1.404(3) . ? O2 C26 1.339(2) . ? O2 C25 1.448(3) . ? C2 C3 1.388(3) . ? C2 C26 1.499(3) . ? C3 C4 1.392(3) . ? C3 H3 0.9500 . ? O3 C27 1.334(3) . ? O3 C28 1.443(3) . ? C4 C5 1.389(3) . ? C4 C7 1.533(3) . ? O4 C27 1.194(3) . ? O5 C14 1.369(3) . ? O5 C17 1.417(3) . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C6 C27 1.498(3) . ? O6 C21 1.375(2) . ? O6 C24 1.426(3) . ? C7 C10 1.515(3) . ? C7 C8 1.532(4) . ? C7 C9 1.533(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.383(3) . ? C11 C16 1.389(3) . ? C12 C13 1.386(3) . ? C12 H12 0.9500 . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C15 1.390(3) . ? C15 C16 1.385(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C23 1.383(3) . ? C18 C19 1.397(3) . ? C19 C20 1.379(3) . ? C19 H19 0.9500 . ? C20 C21 1.385(3) . ? C20 H20 0.9500 . ? C21 C22 1.386(3) . ? C22 C23 1.393(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 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 C18 N1 C1 C6 -52.5(3) . . . . ? C11 N1 C1 C6 130.5(2) . . . . ? C18 N1 C1 C2 129.9(2) . . . . ? C11 N1 C1 C2 -47.1(3) . . . . ? C6 C1 C2 C3 -2.1(3) . . . . ? N1 C1 C2 C3 175.60(18) . . . . ? C6 C1 C2 C26 176.02(18) . . . . ? N1 C1 C2 C26 -6.3(3) . . . . ? C1 C2 C3 C4 4.9(3) . . . . ? C26 C2 C3 C4 -173.28(18) . . . . ? C2 C3 C4 C5 -2.4(3) . . . . ? C2 C3 C4 C7 179.27(19) . . . . ? C3 C4 C5 C6 -2.8(3) . . . . ? C7 C4 C5 C6 175.4(2) . . . . ? C4 C5 C6 C1 5.7(3) . . . . ? C4 C5 C6 C27 -168.14(19) . . . . ? C2 C1 C6 C5 -3.1(3) . . . . ? N1 C1 C6 C5 179.31(18) . . . . ? C2 C1 C6 C27 170.19(19) . . . . ? N1 C1 C6 C27 -7.4(3) . . . . ? C5 C4 C7 C10 6.4(3) . . . . ? C3 C4 C7 C10 -175.4(2) . . . . ? C5 C4 C7 C8 -114.8(3) . . . . ? C3 C4 C7 C8 63.4(3) . . . . ? C5 C4 C7 C9 126.4(2) . . . . ? C3 C4 C7 C9 -55.4(3) . . . . ? C1 N1 C11 C12 127.2(2) . . . . ? C18 N1 C11 C12 -49.9(3) . . . . ? C1 N1 C11 C16 -51.2(3) . . . . ? C18 N1 C11 C16 131.74(19) . . . . ? C16 C11 C12 C13 1.7(3) . . . . ? N1 C11 C12 C13 -176.68(19) . . . . ? C11 C12 C13 C14 0.1(3) . . . . ? C17 O5 C14 C13 -10.9(3) . . . . ? C17 O5 C14 C15 170.1(2) . . . . ? C12 C13 C14 O5 179.6(2) . . . . ? C12 C13 C14 C15 -1.5(3) . . . . ? O5 C14 C15 C16 -179.92(19) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C14 C15 C16 C11 0.7(3) . . . . ? C12 C11 C16 C15 -2.0(3) . . . . ? N1 C11 C16 C15 176.34(18) . . . . ? C1 N1 C18 C23 -35.0(3) . . . . ? C11 N1 C18 C23 142.0(2) . . . . ? C1 N1 C18 C19 147.9(2) . . . . ? C11 N1 C18 C19 -35.2(3) . . . . ? C23 C18 C19 C20 -1.7(3) . . . . ? N1 C18 C19 C20 175.5(2) . . . . ? C18 C19 C20 C21 0.8(3) . . . . ? C24 O6 C21 C20 175.9(2) . . . . ? C24 O6 C21 C22 -4.3(3) . . . . ? C19 C20 C21 O6 -179.0(2) . . . . ? C19 C20 C21 C22 1.2(3) . . . . ? O6 C21 C22 C23 177.9(2) . . . . ? C20 C21 C22 C23 -2.2(3) . . . . ? C19 C18 C23 C22 0.7(3) . . . . ? N1 C18 C23 C22 -176.50(19) . . . . ? C21 C22 C23 C18 1.3(3) . . . . ? C25 O2 C26 O1 0.2(3) . . . . ? C25 O2 C26 C2 -176.11(19) . . . . ? C3 C2 C26 O1 -59.8(3) . . . . ? C1 C2 C26 O1 122.0(2) . . . . ? C3 C2 C26 O2 116.49(19) . . . . ? C1 C2 C26 O2 -61.7(2) . . . . ? C28 O3 C27 O4 2.7(4) . . . . ? C28 O3 C27 C6 -171.9(2) . . . . ? C5 C6 C27 O4 -49.8(3) . . . . ? C1 C6 C27 O4 136.6(3) . . . . ? C5 C6 C27 O3 124.6(2) . . . . ? C1 C6 C27 O3 -49.0(3) . . . . ?