#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:34:08 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257387 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557371.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_1557371 loop_ _publ_author_name 'Sasaki, Yui' 'Kojima, Soya' 'Hamedpour, Vahid' 'Kubota, Riku' 'Takizawa, Shin-ya' 'Yoshikawa, Isao' 'Houjou, Hirohiko' 'Kubo, Yuji' 'Minami, Tsuyoshi' _publ_section_title ; Accurate chiral pattern recognition for amines from just a single chemosensor ; _journal_issue 15 _journal_name_full 'Chemical Science' _journal_page_first 3790 _journal_page_last 3796 _journal_paper_doi 10.1039/D0SC00194E _journal_volume 11 _journal_year 2020 _chemical_absolute_configuration syn _chemical_formula_moiety 'C27 H19 N O3' _chemical_formula_sum 'C27 H19 N O3' _chemical_formula_weight 405.43 _chemical_name_systematic (R)-2-hydroxy-2?-(2-pyridylmethyloxy)-3-formyl-1,1?-binaphthalene _space_group_crystal_system triclinic _space_group_IT_number 1 _space_group_name_Hall 'P 1' _space_group_name_H-M_alt 'P 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/1 _audit_update_record ; 2020-01-11 deposited with the CCDC. 2020-02-24 downloaded from the CCDC. ; _cell_angle_alpha 88.9786(16) _cell_angle_beta 79.0044(17) _cell_angle_gamma 74.6213(19) _cell_formula_units_Z 2 _cell_length_a 7.1378(2) _cell_length_b 9.8466(2) _cell_length_c 14.7942(3) _cell_measurement_reflns_used 9128 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 28.8780 _cell_measurement_theta_min 3.0060 _cell_volume 983.56(4) _computing_cell_refinement 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)' _computing_molecular_graphics 'CrystalStructure 4.2.4' _computing_publication_material 'CrystalStructure 4.2.4 (Rigaku, 2016)' _computing_structure_refinement 'SHELXL-2018/1 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS Version 2013/1 (Sheldrick, 2008)' _diffrn_ambient_temperature 93(2) _diffrn_detector_area_resol_mean 5.811 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.876 _diffrn_measurement_device_type 'Rigaku XtaLAB P200' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_unetI/netI 0.0268 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.876 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 15510 _diffrn_reflns_point_group_measured_fraction_full 0.865 _diffrn_reflns_point_group_measured_fraction_max 0.712 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.818 _diffrn_reflns_theta_min 2.807 _diffrn_source 'rotating anode X-ray generator' _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.90546 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.369 _exptl_crystal_description prism _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.220 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.303 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.043 _refine_ls_abs_structure_details ; Flack x determined using 2500 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.2(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 567 _refine_ls_number_reflns 7323 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0337 _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^)+(0.0537P)^2^+0.1283P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0904 _refine_ls_wR_factor_ref 0.0923 _reflns_Friedel_coverage 0.625 _reflns_Friedel_fraction_full 0.731 _reflns_Friedel_fraction_max 0.548 _reflns_number_gt 6806 _reflns_number_total 7323 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00194e2.cif _cod_data_source_block RpB _cod_depositor_comments ;Adding full bibliography for 1557371.cif. Adding full bibliography for 1557371.cif. ; _cod_database_code 1557371 _shelx_shelxl_version_number 2018/1 _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 0.981 _shelx_estimated_absorpt_t_max 0.995 _oxdiff_exptl_absorpt_empirical_full_min 0.808 _oxdiff_exptl_absorpt_empirical_full_max 1.478 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _shelx_res_file ; TITL RpB RpB.res created by SHELXL-2018/1 at 13:02:56 on 23-May-2019 CELL 0.71073 7.1378 9.8466 14.7942 88.9786 79.0044 74.6213 ZERR 2.0 0.0002 0.0002 0.0003 0.0016 0.0017 0.0019 LATT -1 REM SPGR P1 triclinic SFAC C H N O UNIT 54.000000 38.000000 2.000000 6.000000 SIZE 0.22 0.10 0.06 TEMP -180.0 L.S. 30 FMAP 2 PLAN -20 ACTA CONF BOND$H EQIV $1 x, y, z-1 HTAB C1 O6_$1 HTAB O2 O1 HTAB O5 O4 LIST 4 WGHT 0.053700 0.128300 FVAR 3.12849 O1 4 0.198015 0.469452 -0.053410 11.00000 0.01737 0.01553 = 0.02325 0.00249 -0.00403 -0.00245 C1 1 0.314381 0.361771 -0.091489 11.00000 0.01305 0.01897 = 0.01534 0.00194 -0.00194 -0.00760 AFIX 43 H1 2 0.344387 0.357020 -0.156927 11.00000 -1.20000 AFIX 0 C2 1 0.409567 0.240693 -0.042894 11.00000 0.01038 0.01417 = 0.01635 0.00215 -0.00282 -0.00675 C3 1 0.535010 0.124219 -0.093159 11.00000 0.01396 0.01968 = 0.01110 -0.00073 -0.00207 -0.00866 AFIX 43 H2 2 0.557779 0.124609 -0.158549 11.00000 -1.20000 AFIX 0 C4 1 0.629820 0.004879 -0.049336 11.00000 0.01228 0.01341 = 0.01561 0.00030 -0.00232 -0.00627 C5 1 0.765295 -0.114438 -0.100211 11.00000 0.01614 0.01657 = 0.01506 -0.00396 -0.00041 -0.00610 AFIX 43 H3 2 0.786017 -0.116635 -0.165595 11.00000 -1.20000 AFIX 0 C6 1 0.865389 -0.225195 -0.056708 11.00000 0.01722 0.01552 = 0.02426 -0.00530 -0.00212 -0.00265 AFIX 43 H4 2 0.957770 -0.302871 -0.091559 11.00000 -1.20000 AFIX 0 C7 1 0.831187 -0.224071 0.040637 11.00000 0.01962 0.01309 = 0.02284 0.00248 -0.00700 -0.00285 AFIX 43 H5 2 0.901709 -0.301453 0.070755 11.00000 -1.20000 AFIX 0 C8 1 0.697918 -0.113194 0.092448 11.00000 0.01808 0.01673 = 0.01537 0.00144 -0.00566 -0.00629 AFIX 43 H6 2 0.673486 -0.116376 0.157758 11.00000 -1.20000 AFIX 0 C9 1 0.596232 0.006315 0.049103 11.00000 0.01200 0.01271 = 0.01580 -0.00007 -0.00234 -0.00590 C10 1 0.465371 0.126761 0.101234 11.00000 0.01292 0.01512 = 0.01260 -0.00028 -0.00285 -0.00544 C11 1 0.374518 0.240839 0.055554 11.00000 0.01169 0.01520 = 0.01584 -0.00207 -0.00091 -0.00547 O2 4 0.251405 0.356188 0.105447 11.00000 0.01925 0.01491 = 0.01671 -0.00064 -0.00229 0.00201 H7 2 0.212388 0.418717 0.068089 11.00000 0.01710 C12 1 0.426329 0.130796 0.204330 11.00000 0.01271 0.01384 = 0.01108 0.00022 -0.00131 -0.00112 C13 1 0.277686 0.072075 0.254709 11.00000 0.01431 0.01268 = 0.01485 -0.00038 -0.00187 0.00121 C14 1 0.165509 0.002163 0.210719 11.00000 0.01734 0.01394 = 0.01660 0.00108 -0.00438 -0.00046 AFIX 43 H8 2 0.192940 -0.008923 0.145466 11.00000 -1.20000 AFIX 0 C15 1 0.019423 -0.048891 0.261290 11.00000 0.01829 0.01673 = 0.02636 0.00099 -0.00533 -0.00487 AFIX 43 H9 2 -0.054679 -0.093756 0.230675 11.00000 -1.20000 AFIX 0 C16 1 -0.023060 -0.035826 0.358803 11.00000 0.01796 0.01832 = 0.02251 0.00411 0.00377 -0.00460 AFIX 43 H10 2 -0.126175 -0.070631 0.393171 11.00000 -1.20000 AFIX 0 C17 1 0.084366 0.026752 0.403044 11.00000 0.02028 0.01676 = 0.01592 0.00264 0.00202 -0.00006 AFIX 43 H11 2 0.057143 0.033370 0.468464 11.00000 -1.20000 AFIX 0 C18 1 0.236531 0.082375 0.353144 11.00000 0.01674 0.01412 = 0.01390 0.00137 -0.00125 -0.00018 C19 1 0.346924 0.149853 0.397813 11.00000 0.01843 0.01950 = 0.01146 -0.00071 -0.00133 0.00084 AFIX 43 H12 2 0.320948 0.157119 0.463208 11.00000 -1.20000 AFIX 0 C20 1 0.489739 0.204664 0.349062 11.00000 0.01624 0.01991 = 0.01496 -0.00176 -0.00477 -0.00378 AFIX 43 H13 2 0.562140 0.249639 0.380652 11.00000 -1.20000 AFIX 0 C21 1 0.531212 0.195244 0.251905 11.00000 0.01367 0.01479 = 0.01603 0.00091 -0.00093 -0.00213 O3 4 0.671937 0.249864 0.198595 11.00000 0.01728 0.02619 = 0.01327 -0.00227 -0.00185 -0.01187 C22 1 0.798790 0.306458 0.241701 11.00000 0.01437 0.01703 = 0.01623 -0.00038 -0.00399 -0.00381 AFIX 23 H14 2 0.924863 0.298195 0.197676 11.00000 -1.20000 H15 2 0.829616 0.249512 0.295432 11.00000 -1.20000 AFIX 0 C23 1 0.710374 0.458942 0.273562 11.00000 0.02310 0.01582 = 0.01068 0.00182 0.00035 -0.00214 N1 3 0.838490 0.513195 0.307724 11.00000 0.03705 0.01622 = 0.02037 -0.00081 -0.01008 -0.00664 C24 1 0.774837 0.648456 0.337279 11.00000 0.05884 0.01798 = 0.02640 -0.00069 -0.01263 -0.01107 AFIX 43 H16 2 0.862893 0.687680 0.362209 11.00000 -1.20000 AFIX 0 C25 1 0.590860 0.733451 0.333739 11.00000 0.06018 0.01802 = 0.02306 0.00037 -0.00131 -0.00109 AFIX 43 H17 2 0.553521 0.829139 0.354928 11.00000 -1.20000 AFIX 0 C26 1 0.461502 0.677811 0.299017 11.00000 0.03412 0.02678 = 0.02674 0.01083 0.00751 0.01206 AFIX 43 H18 2 0.332406 0.734496 0.296348 11.00000 -1.20000 AFIX 0 C27 1 0.521146 0.536062 0.267315 11.00000 0.02194 0.02663 = 0.01765 0.00598 0.00107 0.00125 AFIX 43 H19 2 0.434671 0.494977 0.242576 11.00000 -1.20000 AFIX 0 O4 4 0.392066 0.733293 0.973524 11.00000 0.02017 0.01666 = 0.02208 -0.00254 -0.00237 0.00065 C28 1 0.492767 0.630098 1.005570 11.00000 0.01827 0.01616 = 0.01517 -0.00016 -0.00137 -0.00508 AFIX 43 H20 2 0.474187 0.625587 1.070760 11.00000 -1.20000 AFIX 0 C29 1 0.639241 0.513407 0.951312 11.00000 0.01232 0.01560 = 0.01441 -0.00196 -0.00132 -0.00566 C30 1 0.735591 0.399668 0.995278 11.00000 0.01273 0.01455 = 0.01207 0.00158 -0.00277 -0.00634 AFIX 43 H21 2 0.710157 0.400753 1.060713 11.00000 -1.20000 AFIX 0 C31 1 0.871348 0.281200 0.945979 11.00000 0.01173 0.01381 = 0.01424 -0.00055 -0.00256 -0.00587 C32 1 0.966584 0.162250 0.990877 11.00000 0.01383 0.01443 = 0.01513 0.00160 -0.00428 -0.00620 AFIX 43 H22 2 0.940392 0.161778 1.056280 11.00000 -1.20000 AFIX 0 C33 1 1.096214 0.047448 0.941626 11.00000 0.01110 0.01448 = 0.02061 0.00287 -0.00495 -0.00407 AFIX 43 H23 2 1.159513 -0.031901 0.972533 11.00000 -1.20000 AFIX 0 C34 1 1.134337 0.048695 0.844535 11.00000 0.01221 0.01479 = 0.02010 -0.00303 -0.00229 -0.00205 AFIX 43 H24 2 1.224291 -0.030551 0.810253 11.00000 -1.20000 AFIX 0 C35 1 1.044012 0.162150 0.798644 11.00000 0.01293 0.01595 = 0.01373 -0.00101 0.00009 -0.00632 AFIX 43 H25 2 1.072215 0.160183 0.733202 11.00000 -1.20000 AFIX 0 C36 1 0.908987 0.282441 0.847613 11.00000 0.00915 0.01317 = 0.01370 0.00024 -0.00139 -0.00518 C37 1 0.811089 0.401806 0.801859 11.00000 0.01176 0.01346 = 0.01120 0.00001 -0.00102 -0.00610 C38 1 0.678118 0.513895 0.852665 11.00000 0.01411 0.01332 = 0.01434 0.00261 -0.00547 -0.00545 O5 4 0.582209 0.625079 0.808039 11.00000 0.02372 0.01252 = 0.01489 -0.00051 -0.00339 0.00206 H26 2 0.507702 0.681697 0.852344 11.00000 0.02764 C39 1 0.855028 0.403680 0.698896 11.00000 0.01415 0.01099 = 0.01222 -0.00014 -0.00229 -0.00056 C40 1 1.005581 0.463677 0.652172 11.00000 0.01200 0.00927 = 0.01358 0.00074 -0.00151 -0.00019 C41 1 1.117442 0.527314 0.699963 11.00000 0.01459 0.01129 = 0.01487 -0.00035 -0.00242 -0.00120 AFIX 43 H27 2 1.087522 0.534392 0.765370 11.00000 -1.20000 AFIX 0 C42 1 1.268122 0.578653 0.652788 11.00000 0.01558 0.01216 = 0.02042 -0.00041 -0.00294 -0.00299 AFIX 43 H28 2 1.342523 0.619543 0.685827 11.00000 -1.20000 AFIX 0 C43 1 1.313214 0.570991 0.555205 11.00000 0.01467 0.01296 = 0.02379 0.00136 0.00201 -0.00356 AFIX 43 H29 2 1.418617 0.605677 0.523096 11.00000 -1.20000 AFIX 0 C44 1 1.205101 0.513659 0.507074 11.00000 0.01721 0.01508 = 0.01520 0.00190 0.00111 -0.00234 AFIX 43 H30 2 1.233694 0.511442 0.441631 11.00000 -1.20000 AFIX 0 C45 1 1.050900 0.457540 0.553807 11.00000 0.01345 0.01194 = 0.01484 0.00110 -0.00181 0.00017 C46 1 0.943780 0.392198 0.505130 11.00000 0.01794 0.01624 = 0.01008 0.00011 -0.00155 -0.00067 AFIX 43 H31 2 0.972810 0.388216 0.439682 11.00000 -1.20000 AFIX 0 C47 1 0.799359 0.334764 0.550676 11.00000 0.01750 0.01694 = 0.01294 -0.00227 -0.00548 -0.00219 AFIX 43 H32 2 0.728824 0.291080 0.517135 11.00000 -1.20000 AFIX 0 C48 1 0.755487 0.340838 0.648435 11.00000 0.01193 0.01233 = 0.01372 -0.00008 0.00055 -0.00260 O6 4 0.615322 0.281948 0.698753 11.00000 0.01617 0.01905 = 0.01488 -0.00026 -0.00253 -0.00918 C49 1 0.487250 0.229673 0.653585 11.00000 0.01313 0.01488 = 0.01647 -0.00312 -0.00127 -0.00443 AFIX 23 H33 2 0.471516 0.281758 0.596458 11.00000 -1.20000 H34 2 0.355065 0.248490 0.694162 11.00000 -1.20000 AFIX 0 C50 1 0.561643 0.074139 0.629382 11.00000 0.01670 0.01618 = 0.00786 0.00126 -0.00052 -0.00438 N2 3 0.426460 0.021068 0.602598 11.00000 0.02117 0.01571 = 0.01739 0.00022 -0.00507 -0.00629 C51 1 0.477446 -0.117179 0.581609 11.00000 0.02584 0.01827 = 0.02526 -0.00181 -0.00835 -0.00707 AFIX 43 H35 2 0.382884 -0.155827 0.561756 11.00000 -1.20000 AFIX 0 C52 1 0.660534 -0.207296 0.587186 11.00000 0.03063 0.01255 = 0.02772 -0.00181 -0.00658 -0.00236 AFIX 43 H36 2 0.690027 -0.305077 0.572247 11.00000 -1.20000 AFIX 0 C53 1 0.798799 -0.150634 0.615119 11.00000 0.02124 0.01898 = 0.02544 0.00192 -0.00548 0.00178 AFIX 43 H37 2 0.925672 -0.208992 0.619932 11.00000 -1.20000 AFIX 0 C54 1 0.749201 -0.007038 0.636026 11.00000 0.01762 0.01958 = 0.02025 0.00041 -0.00467 -0.00518 AFIX 43 H38 2 0.842117 0.034774 0.654538 11.00000 -1.20000 AFIX 0 HKLF 4 REM RpB REM R1 = 0.0337 for 6806 Fo > 4sig(Fo) and 0.0368 for all 7323 data REM 567 parameters refined using 3 restraints END WGHT 0.0538 0.1284 REM Highest difference peak 0.303, deepest hole -0.228, 1-sigma level 0.043 Q1 1 0.8886 0.2808 0.8995 11.00000 0.05 0.30 Q2 1 0.7974 0.3225 0.6018 11.00000 0.05 0.29 Q3 1 0.6297 0.5009 0.9075 11.00000 0.05 0.27 Q4 1 0.5922 -0.0047 0.0005 11.00000 0.05 0.26 Q5 1 0.3905 0.2364 0.0063 11.00000 0.05 0.25 Q6 1 0.9055 0.3554 0.8256 11.00000 0.05 0.25 Q7 1 1.0299 0.4609 0.6007 11.00000 0.05 0.25 Q8 1 0.8350 0.4029 0.7561 11.00000 0.05 0.24 Q9 1 0.3681 0.1657 0.0774 11.00000 0.05 0.24 Q10 1 0.5005 0.2098 0.3018 11.00000 0.05 0.24 Q11 1 0.4493 0.1250 0.1575 11.00000 0.05 0.24 Q12 1 0.6436 0.0198 -0.0019 11.00000 0.05 0.24 Q13 1 0.8852 0.4665 0.6776 11.00000 0.05 0.23 Q14 1 0.2333 0.0948 0.3019 11.00000 0.05 0.22 Q15 1 0.4526 0.2016 0.0802 11.00000 0.05 0.22 Q16 1 0.7859 0.4742 0.8244 11.00000 0.05 0.21 Q17 1 0.4313 0.1848 -0.0623 11.00000 0.05 0.21 Q18 1 0.3636 0.6441 0.2805 11.00000 0.05 0.21 Q19 1 0.6471 0.4422 0.9738 11.00000 0.05 0.20 Q20 1 0.4866 0.0569 0.0784 11.00000 0.05 0.20 ; _shelx_res_checksum 28077 loop_ _space_group_symop_operation_xyz '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 O1 O 0.1980(2) 0.46945(16) -0.05341(11) 0.0191(4) Uani 1 1 d . . . . . C1 C 0.3144(3) 0.3618(2) -0.09149(15) 0.0153(5) Uani 1 1 d . . . . . H1 H 0.344387 0.357020 -0.156927 0.018 Uiso 1 1 calc R U . . . C2 C 0.4096(3) 0.2407(2) -0.04289(15) 0.0129(4) Uani 1 1 d . . . . . C3 C 0.5350(3) 0.1242(2) -0.09316(15) 0.0141(4) Uani 1 1 d . . . . . H2 H 0.557779 0.124609 -0.158549 0.017 Uiso 1 1 calc R U . . . C4 C 0.6298(3) 0.0049(2) -0.04934(14) 0.0133(4) Uani 1 1 d . . . . . C5 C 0.7653(4) -0.1144(2) -0.10021(15) 0.0159(5) Uani 1 1 d . . . . . H3 H 0.786017 -0.116635 -0.165595 0.019 Uiso 1 1 calc R U . . . C6 C 0.8654(4) -0.2252(2) -0.05671(16) 0.0195(5) Uani 1 1 d . . . . . H4 H 0.957770 -0.302871 -0.091559 0.023 Uiso 1 1 calc R U . . . C7 C 0.8312(3) -0.2241(2) 0.04064(15) 0.0184(4) Uani 1 1 d . . . . . H5 H 0.901709 -0.301453 0.070755 0.022 Uiso 1 1 calc R U . . . C8 C 0.6979(4) -0.1132(2) 0.09245(15) 0.0161(5) Uani 1 1 d . . . . . H6 H 0.673486 -0.116376 0.157758 0.019 Uiso 1 1 calc R U . . . C9 C 0.5962(3) 0.0063(2) 0.04910(15) 0.0130(4) Uani 1 1 d . . . . . C10 C 0.4654(3) 0.1268(2) 0.10123(14) 0.0132(4) Uani 1 1 d . . . . . C11 C 0.3745(3) 0.2408(2) 0.05555(15) 0.0141(5) Uani 1 1 d . . . . . O2 O 0.2514(3) 0.35619(18) 0.10545(11) 0.0184(4) Uani 1 1 d . . . . . H7 H 0.212(4) 0.419(3) 0.0681(17) 0.017(6) Uiso 1 1 d . . . . . C12 C 0.4263(3) 0.1308(2) 0.20433(14) 0.0131(4) Uani 1 1 d . . . . . C13 C 0.2777(3) 0.0721(2) 0.25471(15) 0.0150(5) Uani 1 1 d . . . . . C14 C 0.1655(3) 0.0022(2) 0.21072(15) 0.0165(5) Uani 1 1 d . . . . . H8 H 0.192940 -0.008923 0.145466 0.020 Uiso 1 1 calc R U . . . C15 C 0.0194(4) -0.0489(2) 0.26129(17) 0.0203(5) Uani 1 1 d . . . . . H9 H -0.054679 -0.093756 0.230675 0.024 Uiso 1 1 calc R U . . . C16 C -0.0231(4) -0.0358(2) 0.35880(16) 0.0207(5) Uani 1 1 d . . . . . H10 H -0.126175 -0.070631 0.393171 0.025 Uiso 1 1 calc R U . . . C17 C 0.0844(4) 0.0268(2) 0.40304(15) 0.0194(5) Uani 1 1 d . . . . . H11 H 0.057143 0.033370 0.468464 0.023 Uiso 1 1 calc R U . . . C18 C 0.2365(3) 0.0824(2) 0.35314(14) 0.0159(5) Uani 1 1 d . . . . . C19 C 0.3469(3) 0.1499(2) 0.39781(15) 0.0178(5) Uani 1 1 d . . . . . H12 H 0.320948 0.157119 0.463208 0.021 Uiso 1 1 calc R U . . . C20 C 0.4897(3) 0.2047(2) 0.34906(15) 0.0170(5) Uani 1 1 d . . . . . H13 H 0.562140 0.249639 0.380652 0.020 Uiso 1 1 calc R U . . . C21 C 0.5312(3) 0.1952(2) 0.25190(15) 0.0154(5) Uani 1 1 d . . . . . O3 O 0.6719(2) 0.24986(18) 0.19860(10) 0.0179(4) Uani 1 1 d . . . . . C22 C 0.7988(4) 0.3065(2) 0.24170(16) 0.0158(5) Uani 1 1 d . . . . . H14 H 0.924863 0.298195 0.197676 0.019 Uiso 1 1 calc R U . . . H15 H 0.829616 0.249512 0.295432 0.019 Uiso 1 1 calc R U . . . C23 C 0.7104(4) 0.4589(2) 0.27356(14) 0.0176(5) Uani 1 1 d . . . . . N1 N 0.8385(4) 0.5132(2) 0.30772(14) 0.0240(5) Uani 1 1 d . . . . . C24 C 0.7748(5) 0.6485(3) 0.33728(18) 0.0336(7) Uani 1 1 d . . . . . H16 H 0.862893 0.687680 0.362209 0.040 Uiso 1 1 calc R U . . . C25 C 0.5909(5) 0.7335(3) 0.33374(19) 0.0365(7) Uani 1 1 d . . . . . H17 H 0.553521 0.829139 0.354928 0.044 Uiso 1 1 calc R U . . . C26 C 0.4615(5) 0.6778(3) 0.29902(18) 0.0351(7) Uani 1 1 d . . . . . H18 H 0.332406 0.734496 0.296348 0.042 Uiso 1 1 calc R U . . . C27 C 0.5211(4) 0.5361(3) 0.26731(16) 0.0243(5) Uani 1 1 d . . . . . H19 H 0.434671 0.494977 0.242576 0.029 Uiso 1 1 calc R U . . . O4 O 0.3921(2) 0.73329(17) 0.97352(11) 0.0209(4) Uani 1 1 d . . . . . C28 C 0.4928(4) 0.6301(2) 1.00557(15) 0.0167(5) Uani 1 1 d . . . . . H20 H 0.474187 0.625587 1.070760 0.020 Uiso 1 1 calc R U . . . C29 C 0.6392(3) 0.5134(2) 0.95131(14) 0.0139(5) Uani 1 1 d . . . . . C30 C 0.7356(3) 0.3997(2) 0.99528(14) 0.0126(4) Uani 1 1 d . . . . . H21 H 0.710157 0.400753 1.060713 0.015 Uiso 1 1 calc R U . . . C31 C 0.8713(3) 0.2812(2) 0.94598(14) 0.0128(4) Uani 1 1 d . . . . . C32 C 0.9666(3) 0.1623(2) 0.99088(15) 0.0138(5) Uani 1 1 d . . . . . H22 H 0.940392 0.161778 1.056280 0.017 Uiso 1 1 calc R U . . . C33 C 1.0962(3) 0.0474(2) 0.94163(16) 0.0150(4) Uani 1 1 d . . . . . H23 H 1.159513 -0.031901 0.972533 0.018 Uiso 1 1 calc R U . . . C34 C 1.1343(3) 0.0487(2) 0.84453(14) 0.0161(4) Uani 1 1 d . . . . . H24 H 1.224291 -0.030551 0.810253 0.019 Uiso 1 1 calc R U . . . C35 C 1.0440(3) 0.1622(2) 0.79864(15) 0.0141(5) Uani 1 1 d . . . . . H25 H 1.072215 0.160183 0.733202 0.017 Uiso 1 1 calc R U . . . C36 C 0.9090(3) 0.2824(2) 0.84761(14) 0.0117(4) Uani 1 1 d . . . . . C37 C 0.8111(3) 0.4018(2) 0.80186(14) 0.0118(4) Uani 1 1 d . . . . . C38 C 0.6781(3) 0.5139(2) 0.85266(14) 0.0132(4) Uani 1 1 d . . . . . O5 O 0.5822(3) 0.62508(17) 0.80804(11) 0.0184(4) Uani 1 1 d . . . . . H26 H 0.508(4) 0.682(3) 0.852(2) 0.028(8) Uiso 1 1 d . . . . . C39 C 0.8550(3) 0.4037(2) 0.69890(14) 0.0130(4) Uani 1 1 d . . . . . C40 C 1.0056(3) 0.4637(2) 0.65217(14) 0.0123(4) Uani 1 1 d . . . . . C41 C 1.1174(3) 0.5273(2) 0.69996(15) 0.0141(4) Uani 1 1 d . . . . . H27 H 1.087522 0.534392 0.765370 0.017 Uiso 1 1 calc R U . . . C42 C 1.2681(3) 0.5787(2) 0.65279(16) 0.0163(5) Uani 1 1 d . . . . . H28 H 1.342523 0.619543 0.685827 0.020 Uiso 1 1 calc R U . . . C43 C 1.3132(3) 0.5710(2) 0.55520(16) 0.0180(5) Uani 1 1 d . . . . . H29 H 1.418617 0.605677 0.523096 0.022 Uiso 1 1 calc R U . . . C44 C 1.2051(3) 0.5137(2) 0.50707(15) 0.0168(5) Uani 1 1 d . . . . . H30 H 1.233694 0.511442 0.441631 0.020 Uiso 1 1 calc R U . . . C45 C 1.0509(3) 0.4575(2) 0.55381(14) 0.0142(4) Uani 1 1 d . . . . . C46 C 0.9438(3) 0.3922(2) 0.50513(14) 0.0157(5) Uani 1 1 d . . . . . H31 H 0.972810 0.388216 0.439682 0.019 Uiso 1 1 calc R U . . . C47 C 0.7994(3) 0.3348(2) 0.55068(14) 0.0159(5) Uani 1 1 d . . . . . H32 H 0.728824 0.291080 0.517135 0.019 Uiso 1 1 calc R U . . . C48 C 0.7555(3) 0.3408(2) 0.64844(14) 0.0132(4) Uani 1 1 d . . . . . O6 O 0.6153(2) 0.28195(16) 0.69875(10) 0.0159(3) Uani 1 1 d . . . . . C49 C 0.4872(3) 0.2297(2) 0.65358(16) 0.0149(4) Uani 1 1 d . . . . . H33 H 0.471516 0.281758 0.596458 0.018 Uiso 1 1 calc R U . . . H34 H 0.355065 0.248490 0.694162 0.018 Uiso 1 1 calc R U . . . C50 C 0.5616(3) 0.0741(2) 0.62938(14) 0.0138(5) Uani 1 1 d . . . . . N2 N 0.4265(3) 0.0211(2) 0.60260(13) 0.0176(4) Uani 1 1 d . . . . . C51 C 0.4774(4) -0.1172(3) 0.58161(17) 0.0224(5) Uani 1 1 d . . . . . H35 H 0.382884 -0.155827 0.561756 0.027 Uiso 1 1 calc R U . . . C52 C 0.6605(4) -0.2073(2) 0.58719(17) 0.0241(5) Uani 1 1 d . . . . . H36 H 0.690027 -0.305077 0.572247 0.029 Uiso 1 1 calc R U . . . C53 C 0.7988(4) -0.1506(3) 0.61512(17) 0.0232(5) Uani 1 1 d . . . . . H37 H 0.925672 -0.208992 0.619932 0.028 Uiso 1 1 calc R U . . . C54 C 0.7492(4) -0.0070(2) 0.63603(16) 0.0190(5) Uani 1 1 d . . . . . H38 H 0.842117 0.034774 0.654538 0.023 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 0.0174(8) 0.0155(8) 0.0233(8) 0.0025(6) -0.0040(7) -0.0024(6) C1 0.0130(12) 0.0190(12) 0.0153(10) 0.0019(9) -0.0019(9) -0.0076(10) C2 0.0104(11) 0.0142(11) 0.0164(11) 0.0022(8) -0.0028(9) -0.0067(9) C3 0.0140(11) 0.0197(11) 0.0111(9) -0.0007(8) -0.0021(9) -0.0087(9) C4 0.0123(11) 0.0134(10) 0.0156(10) 0.0003(8) -0.0023(9) -0.0063(9) C5 0.0161(11) 0.0166(11) 0.0151(10) -0.0040(8) -0.0004(9) -0.0061(9) C6 0.0172(12) 0.0155(11) 0.0243(11) -0.0053(9) -0.0021(10) -0.0027(9) C7 0.0196(11) 0.0131(10) 0.0228(11) 0.0025(8) -0.0070(9) -0.0029(8) C8 0.0181(12) 0.0167(11) 0.0154(10) 0.0014(9) -0.0057(9) -0.0063(9) C9 0.0120(11) 0.0127(10) 0.0158(10) -0.0001(8) -0.0023(9) -0.0059(9) C10 0.0129(11) 0.0151(11) 0.0126(10) -0.0003(8) -0.0028(9) -0.0054(9) C11 0.0117(11) 0.0152(11) 0.0158(10) -0.0021(8) -0.0009(9) -0.0055(9) O2 0.0192(9) 0.0149(8) 0.0167(8) -0.0006(6) -0.0023(7) 0.0020(7) C12 0.0127(11) 0.0138(10) 0.0111(10) 0.0002(8) -0.0013(9) -0.0011(9) C13 0.0143(11) 0.0127(10) 0.0149(10) -0.0004(8) -0.0019(9) 0.0012(9) C14 0.0173(12) 0.0139(11) 0.0166(10) 0.0011(8) -0.0044(9) -0.0005(9) C15 0.0183(13) 0.0167(11) 0.0264(12) 0.0010(9) -0.0053(10) -0.0049(10) C16 0.0180(12) 0.0183(12) 0.0225(11) 0.0041(9) 0.0038(10) -0.0046(10) C17 0.0203(13) 0.0168(11) 0.0159(10) 0.0026(9) 0.0020(9) -0.0001(9) C18 0.0167(12) 0.0141(11) 0.0139(10) 0.0014(8) -0.0013(9) -0.0002(9) C19 0.0184(13) 0.0195(11) 0.0115(10) -0.0007(8) -0.0013(9) 0.0008(9) C20 0.0162(12) 0.0199(11) 0.0150(10) -0.0018(9) -0.0048(9) -0.0038(9) C21 0.0137(12) 0.0148(11) 0.0160(11) 0.0009(8) -0.0009(9) -0.0021(9) O3 0.0173(9) 0.0262(9) 0.0133(7) -0.0023(6) -0.0019(7) -0.0119(7) C22 0.0144(11) 0.0170(11) 0.0162(10) -0.0004(8) -0.0040(9) -0.0038(9) C23 0.0231(13) 0.0158(11) 0.0107(10) 0.0018(8) 0.0003(9) -0.0021(10) N1 0.0371(13) 0.0162(10) 0.0204(10) -0.0008(8) -0.0101(9) -0.0066(9) C24 0.059(2) 0.0180(12) 0.0264(13) -0.0007(10) -0.0126(13) -0.0111(13) C25 0.060(2) 0.0180(13) 0.0231(12) 0.0004(10) -0.0013(13) -0.0011(13) C26 0.0341(16) 0.0268(14) 0.0267(13) 0.0108(11) 0.0075(12) 0.0121(12) C27 0.0219(13) 0.0266(13) 0.0176(11) 0.0060(10) 0.0011(10) 0.0013(10) O4 0.0202(9) 0.0167(8) 0.0221(8) -0.0025(6) -0.0024(7) 0.0007(7) C28 0.0183(12) 0.0162(11) 0.0152(10) -0.0002(8) -0.0014(9) -0.0051(9) C29 0.0123(11) 0.0156(11) 0.0144(10) -0.0020(8) -0.0013(9) -0.0057(9) C30 0.0127(11) 0.0145(11) 0.0121(10) 0.0016(8) -0.0028(9) -0.0063(9) C31 0.0117(11) 0.0138(11) 0.0142(10) -0.0005(8) -0.0026(9) -0.0059(9) C32 0.0138(12) 0.0144(11) 0.0151(10) 0.0016(9) -0.0043(9) -0.0062(9) C33 0.0111(11) 0.0145(11) 0.0206(10) 0.0029(8) -0.0050(9) -0.0041(9) C34 0.0122(10) 0.0148(10) 0.0201(10) -0.0030(8) -0.0023(8) -0.0021(8) C35 0.0129(11) 0.0160(11) 0.0137(10) -0.0010(8) 0.0001(9) -0.0063(9) C36 0.0092(11) 0.0132(11) 0.0137(10) 0.0002(8) -0.0014(8) -0.0052(8) C37 0.0118(11) 0.0135(11) 0.0112(10) 0.0000(8) -0.0010(9) -0.0061(9) C38 0.0141(11) 0.0133(10) 0.0143(10) 0.0026(8) -0.0055(9) -0.0055(9) O5 0.0237(9) 0.0125(8) 0.0149(7) -0.0005(6) -0.0034(7) 0.0021(7) C39 0.0142(12) 0.0110(10) 0.0122(10) -0.0001(8) -0.0023(9) -0.0006(9) C40 0.0120(11) 0.0093(10) 0.0136(10) 0.0007(8) -0.0015(9) -0.0002(8) C41 0.0146(11) 0.0113(10) 0.0149(10) -0.0004(8) -0.0024(9) -0.0012(9) C42 0.0156(12) 0.0122(10) 0.0204(11) -0.0004(8) -0.0029(9) -0.0030(9) C43 0.0147(12) 0.0130(11) 0.0238(11) 0.0014(9) 0.0020(9) -0.0036(9) C44 0.0172(12) 0.0151(11) 0.0152(10) 0.0019(8) 0.0011(9) -0.0023(9) C45 0.0134(11) 0.0119(10) 0.0148(10) 0.0011(8) -0.0018(9) 0.0002(8) C46 0.0179(12) 0.0162(11) 0.0101(10) 0.0001(8) -0.0015(9) -0.0007(9) C47 0.0175(12) 0.0169(11) 0.0129(10) -0.0023(8) -0.0055(9) -0.0022(9) C48 0.0119(11) 0.0123(10) 0.0137(10) -0.0001(8) 0.0006(9) -0.0026(8) O6 0.0162(8) 0.0190(8) 0.0149(7) -0.0003(6) -0.0025(6) -0.0092(7) C49 0.0131(11) 0.0149(10) 0.0165(10) -0.0031(8) -0.0013(9) -0.0044(9) C50 0.0167(12) 0.0162(11) 0.0079(9) 0.0013(8) -0.0005(9) -0.0044(9) N2 0.0212(10) 0.0157(9) 0.0174(9) 0.0002(7) -0.0051(8) -0.0063(8) C51 0.0258(13) 0.0183(11) 0.0253(12) -0.0018(9) -0.0083(10) -0.0071(10) C52 0.0306(14) 0.0126(11) 0.0277(12) -0.0018(9) -0.0066(11) -0.0024(10) C53 0.0212(13) 0.0190(12) 0.0254(12) 0.0019(10) -0.0055(10) 0.0018(10) C54 0.0176(12) 0.0196(12) 0.0203(11) 0.0004(9) -0.0047(10) -0.0052(10) 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 O1 C1 C2 124.3(2) . . ? O1 C1 H1 117.8 . . ? C2 C1 H1 117.8 . . ? C3 C2 C11 119.7(2) . . ? C3 C2 C1 119.13(19) . . ? C11 C2 C1 121.1(2) . . ? C2 C3 C4 121.17(19) . . ? C2 C3 H2 119.4 . . ? C4 C3 H2 119.4 . . ? C3 C4 C5 121.89(19) . . ? C3 C4 C9 118.86(19) . . ? C5 C4 C9 119.2(2) . . ? C6 C5 C4 121.1(2) . . ? C6 C5 H3 119.4 . . ? C4 C5 H3 119.4 . . ? C5 C6 C7 119.6(2) . . ? C5 C6 H4 120.2 . . ? C7 C6 H4 120.2 . . ? C8 C7 C6 121.2(2) . . ? C8 C7 H5 119.4 . . ? C6 C7 H5 119.4 . . ? C7 C8 C9 120.5(2) . . ? C7 C8 H6 119.8 . . ? C9 C8 H6 119.8 . . ? C8 C9 C10 121.7(2) . . ? C8 C9 C4 118.27(19) . . ? C10 C9 C4 120.0(2) . . ? C11 C10 C9 119.24(18) . . ? C11 C10 C12 119.6(2) . . ? C9 C10 C12 121.1(2) . . ? O2 C11 C10 119.11(19) . . ? O2 C11 C2 119.9(2) . . ? C10 C11 C2 121.0(2) . . ? C11 O2 H7 108.1(17) . . ? C21 C12 C13 119.24(18) . . ? C21 C12 C10 120.33(19) . . ? C13 C12 C10 120.41(19) . . ? C12 C13 C18 119.6(2) . . ? C12 C13 C14 122.54(19) . . ? C18 C13 C14 117.9(2) . . ? C15 C14 C13 120.9(2) . . ? C15 C14 H8 119.6 . . ? C13 C14 H8 119.6 . . ? C14 C15 C16 120.9(2) . . ? C14 C15 H9 119.6 . . ? C16 C15 H9 119.6 . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H10 120.1 . . ? C15 C16 H10 120.1 . . ? C16 C17 C18 121.2(2) . . ? C16 C17 H11 119.4 . . ? C18 C17 H11 119.4 . . ? C19 C18 C17 121.95(19) . . ? C19 C18 C13 118.7(2) . . ? C17 C18 C13 119.4(2) . . ? C20 C19 C18 121.3(2) . . ? C20 C19 H12 119.4 . . ? C18 C19 H12 119.4 . . ? C19 C20 C21 120.5(2) . . ? C19 C20 H13 119.8 . . ? C21 C20 H13 119.8 . . ? O3 C21 C12 115.92(18) . . ? O3 C21 C20 123.4(2) . . ? C12 C21 C20 120.7(2) . . ? C21 O3 C22 119.56(16) . . ? O3 C22 C23 113.48(19) . . ? O3 C22 H14 108.9 . . ? C23 C22 H14 108.9 . . ? O3 C22 H15 108.9 . . ? C23 C22 H15 108.9 . . ? H14 C22 H15 107.7 . . ? N1 C23 C27 123.3(2) . . ? N1 C23 C22 112.4(2) . . ? C27 C23 C22 124.3(2) . . ? C24 N1 C23 117.1(2) . . ? N1 C24 C25 124.0(3) . . ? N1 C24 H16 118.0 . . ? C25 C24 H16 118.0 . . ? C24 C25 C26 118.6(2) . . ? C24 C25 H17 120.7 . . ? C26 C25 H17 120.7 . . ? C25 C26 C27 119.5(3) . . ? C25 C26 H18 120.2 . . ? C27 C26 H18 120.2 . . ? C23 C27 C26 117.4(3) . . ? C23 C27 H19 121.3 . . ? C26 C27 H19 121.3 . . ? O4 C28 C29 125.0(2) . . ? O4 C28 H20 117.5 . . ? C29 C28 H20 117.5 . . ? C30 C29 C38 119.6(2) . . ? C30 C29 C28 119.60(19) . . ? C38 C29 C28 120.7(2) . . ? C29 C30 C31 121.86(19) . . ? C29 C30 H21 119.1 . . ? C31 C30 H21 119.1 . . ? C30 C31 C32 122.05(19) . . ? C30 C31 C36 118.1(2) . . ? C32 C31 C36 119.80(19) . . ? C33 C32 C31 121.1(2) . . ? C33 C32 H22 119.4 . . ? C31 C32 H22 119.4 . . ? C32 C33 C34 119.2(2) . . ? C32 C33 H23 120.4 . . ? C34 C33 H23 120.4 . . ? C35 C34 C33 121.3(2) . . ? C35 C34 H24 119.4 . . ? C33 C34 H24 119.4 . . ? C34 C35 C36 120.91(19) . . ? C34 C35 H25 119.5 . . ? C36 C35 H25 119.5 . . ? C35 C36 C31 117.7(2) . . ? C35 C36 C37 122.28(18) . . ? C31 C36 C37 120.01(19) . . ? C38 C37 C36 119.81(18) . . ? C38 C37 C39 120.5(2) . . ? C36 C37 C39 119.65(19) . . ? O5 C38 C37 119.10(19) . . ? O5 C38 C29 120.36(19) . . ? C37 C38 C29 120.5(2) . . ? C38 O5 H26 103.5(18) . . ? C48 C39 C40 119.37(18) . . ? C48 C39 C37 119.87(19) . . ? C40 C39 C37 120.69(19) . . ? C39 C40 C41 122.34(18) . . ? C39 C40 C45 119.38(19) . . ? C41 C40 C45 118.26(19) . . ? C42 C41 C40 120.9(2) . . ? C42 C41 H27 119.5 . . ? C40 C41 H27 119.5 . . ? C41 C42 C43 120.4(2) . . ? C41 C42 H28 119.8 . . ? C43 C42 H28 119.8 . . ? C44 C43 C42 120.1(2) . . ? C44 C43 H29 119.9 . . ? C42 C43 H29 119.9 . . ? C43 C44 C45 120.8(2) . . ? C43 C44 H30 119.6 . . ? C45 C44 H30 119.6 . . ? C46 C45 C44 121.46(19) . . ? C46 C45 C40 119.05(19) . . ? C44 C45 C40 119.47(19) . . ? C47 C46 C45 121.13(19) . . ? C47 C46 H31 119.4 . . ? C45 C46 H31 119.4 . . ? C46 C47 C48 119.5(2) . . ? C46 C47 H32 120.2 . . ? C48 C47 H32 120.2 . . ? C39 C48 O6 115.88(18) . . ? C39 C48 C47 121.5(2) . . ? O6 C48 C47 122.57(19) . . ? C48 O6 C49 120.20(17) . . ? O6 C49 C50 113.46(19) . . ? O6 C49 H33 108.9 . . ? C50 C49 H33 108.9 . . ? O6 C49 H34 108.9 . . ? C50 C49 H34 108.9 . . ? H33 C49 H34 107.7 . . ? N2 C50 C54 123.0(2) . . ? N2 C50 C49 113.06(19) . . ? C54 C50 C49 123.9(2) . . ? C50 N2 C51 117.4(2) . . ? N2 C51 C52 123.7(2) . . ? N2 C51 H35 118.1 . . ? C52 C51 H35 118.1 . . ? C53 C52 C51 118.1(2) . . ? C53 C52 H36 121.0 . . ? C51 C52 H36 121.0 . . ? C52 C53 C54 118.9(2) . . ? C52 C53 H37 120.5 . . ? C54 C53 H37 120.5 . . ? C50 C54 C53 118.8(2) . . ? C50 C54 H38 120.6 . . ? C53 C54 H38 120.6 . . ? 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 C1 1.228(3) . ? C1 C2 1.458(3) . ? C1 H1 0.9500 . ? C2 C3 1.379(3) . ? C2 C11 1.430(3) . ? C3 C4 1.406(3) . ? C3 H2 0.9500 . ? C4 C5 1.426(3) . ? C4 C9 1.430(3) . ? C5 C6 1.361(3) . ? C5 H3 0.9500 . ? C6 C7 1.414(3) . ? C6 H4 0.9500 . ? C7 C8 1.373(3) . ? C7 H5 0.9500 . ? C8 C9 1.421(3) . ? C8 H6 0.9500 . ? C9 C10 1.430(3) . ? C10 C11 1.376(3) . ? C10 C12 1.497(3) . ? C11 O2 1.364(3) . ? O2 H7 0.85(3) . ? C12 C21 1.388(3) . ? C12 C13 1.423(3) . ? C13 C18 1.430(3) . ? C13 C14 1.430(3) . ? C14 C15 1.366(3) . ? C14 H8 0.9500 . ? C15 C16 1.417(3) . ? C15 H9 0.9500 . ? C16 C17 1.361(3) . ? C16 H10 0.9500 . ? C17 C18 1.421(3) . ? C17 H11 0.9500 . ? C18 C19 1.411(3) . ? C19 C20 1.359(3) . ? C19 H12 0.9500 . ? C20 C21 1.411(3) . ? C20 H13 0.9500 . ? C21 O3 1.375(3) . ? O3 C22 1.427(3) . ? C22 C23 1.511(3) . ? C22 H14 0.9900 . ? C22 H15 0.9900 . ? C23 N1 1.350(3) . ? C23 C27 1.382(4) . ? N1 C24 1.340(3) . ? C24 C25 1.367(5) . ? C24 H16 0.9500 . ? C25 C26 1.370(4) . ? C25 H17 0.9500 . ? C26 C27 1.408(4) . ? C26 H18 0.9500 . ? C27 H19 0.9500 . ? O4 C28 1.224(3) . ? C28 C29 1.461(3) . ? C28 H20 0.9500 . ? C29 C30 1.373(3) . ? C29 C38 1.433(3) . ? C30 C31 1.412(3) . ? C30 H21 0.9500 . ? C31 C32 1.413(3) . ? C31 C36 1.429(3) . ? C32 C33 1.372(3) . ? C32 H22 0.9500 . ? C33 C34 1.410(3) . ? C33 H23 0.9500 . ? C34 C35 1.372(3) . ? C34 H24 0.9500 . ? C35 C36 1.420(3) . ? C35 H25 0.9500 . ? C36 C37 1.430(3) . ? C37 C38 1.373(3) . ? C37 C39 1.496(3) . ? C38 O5 1.361(3) . ? O5 H26 0.86(3) . ? C39 C48 1.377(3) . ? C39 C40 1.421(3) . ? C40 C41 1.424(3) . ? C40 C45 1.428(3) . ? C41 C42 1.374(3) . ? C41 H27 0.9500 . ? C42 C43 1.417(3) . ? C42 H28 0.9500 . ? C43 C44 1.370(3) . ? C43 H29 0.9500 . ? C44 C45 1.419(3) . ? C44 H30 0.9500 . ? C45 C46 1.416(3) . ? C46 C47 1.366(3) . ? C46 H31 0.9500 . ? C47 C48 1.419(3) . ? C47 H32 0.9500 . ? C48 O6 1.378(3) . ? O6 C49 1.429(3) . ? C49 C50 1.507(3) . ? C49 H33 0.9900 . ? C49 H34 0.9900 . ? C50 N2 1.335(3) . ? C50 C54 1.386(3) . ? N2 C51 1.338(3) . ? C51 C52 1.388(4) . ? C51 H35 0.9500 . ? C52 C53 1.383(4) . ? C52 H36 0.9500 . ? C53 C54 1.389(3) . ? C53 H37 0.9500 . ? C54 H38 0.9500 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C1 H1 O6 0.95 2.56 3.393(3) 146.1 1_554 yes O2 H7 O1 0.85(3) 1.87(3) 2.633(2) 149(2) . yes O5 H26 O4 0.86(3) 1.84(3) 2.651(2) 155(3) . yes 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 O1 C1 C2 C3 178.8(2) . . . . ? O1 C1 C2 C11 -1.1(3) . . . . ? C11 C2 C3 C4 0.0(3) . . . . ? C1 C2 C3 C4 -179.9(2) . . . . ? C2 C3 C4 C5 -177.8(2) . . . . ? C2 C3 C4 C9 -0.8(3) . . . . ? C3 C4 C5 C6 175.7(2) . . . . ? C9 C4 C5 C6 -1.3(3) . . . . ? C4 C5 C6 C7 1.7(3) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 C9 -2.5(3) . . . . ? C7 C8 C9 C10 -176.3(2) . . . . ? C7 C8 C9 C4 2.8(3) . . . . ? C3 C4 C9 C8 -178.0(2) . . . . ? C5 C4 C9 C8 -0.9(3) . . . . ? C3 C4 C9 C10 1.1(3) . . . . ? C5 C4 C9 C10 178.17(19) . . . . ? C8 C9 C10 C11 178.5(2) . . . . ? C4 C9 C10 C11 -0.6(3) . . . . ? C8 C9 C10 C12 -1.4(3) . . . . ? C4 C9 C10 C12 179.6(2) . . . . ? C9 C10 C11 O2 -179.31(19) . . . . ? C12 C10 C11 O2 0.5(3) . . . . ? C9 C10 C11 C2 -0.2(3) . . . . ? C12 C10 C11 C2 179.62(19) . . . . ? C3 C2 C11 O2 179.63(19) . . . . ? C1 C2 C11 O2 -0.5(3) . . . . ? C3 C2 C11 C10 0.5(3) . . . . ? C1 C2 C11 C10 -179.6(2) . . . . ? C11 C10 C12 C21 -83.4(3) . . . . ? C9 C10 C12 C21 96.4(3) . . . . ? C11 C10 C12 C13 94.9(3) . . . . ? C9 C10 C12 C13 -85.3(3) . . . . ? C21 C12 C13 C18 1.0(3) . . . . ? C10 C12 C13 C18 -177.3(2) . . . . ? C21 C12 C13 C14 -179.0(2) . . . . ? C10 C12 C13 C14 2.7(3) . . . . ? C12 C13 C14 C15 -177.8(2) . . . . ? C18 C13 C14 C15 2.1(3) . . . . ? C13 C14 C15 C16 -0.9(4) . . . . ? C14 C15 C16 C17 -0.8(4) . . . . ? C15 C16 C17 C18 1.4(3) . . . . ? C16 C17 C18 C19 178.8(2) . . . . ? C16 C17 C18 C13 -0.1(3) . . . . ? C12 C13 C18 C19 -0.6(3) . . . . ? C14 C13 C18 C19 179.4(2) . . . . ? C12 C13 C18 C17 178.4(2) . . . . ? C14 C13 C18 C17 -1.6(3) . . . . ? C17 C18 C19 C20 -178.9(2) . . . . ? C13 C18 C19 C20 0.1(3) . . . . ? C18 C19 C20 C21 0.0(4) . . . . ? C13 C12 C21 O3 -179.81(19) . . . . ? C10 C12 C21 O3 -1.5(3) . . . . ? C13 C12 C21 C20 -0.9(3) . . . . ? C10 C12 C21 C20 177.4(2) . . . . ? C19 C20 C21 O3 179.2(2) . . . . ? C19 C20 C21 C12 0.4(3) . . . . ? C12 C21 O3 C22 -174.33(19) . . . . ? C20 C21 O3 C22 6.8(3) . . . . ? C21 O3 C22 C23 -85.6(2) . . . . ? O3 C22 C23 N1 -175.31(18) . . . . ? O3 C22 C23 C27 3.6(3) . . . . ? C27 C23 N1 C24 0.6(3) . . . . ? C22 C23 N1 C24 179.5(2) . . . . ? C23 N1 C24 C25 -0.8(4) . . . . ? N1 C24 C25 C26 0.8(4) . . . . ? C24 C25 C26 C27 -0.6(4) . . . . ? N1 C23 C27 C26 -0.4(3) . . . . ? C22 C23 C27 C26 -179.2(2) . . . . ? C25 C26 C27 C23 0.4(3) . . . . ? O4 C28 C29 C30 -176.5(2) . . . . ? O4 C28 C29 C38 1.1(4) . . . . ? C38 C29 C30 C31 -0.8(3) . . . . ? C28 C29 C30 C31 176.9(2) . . . . ? C29 C30 C31 C32 -178.2(2) . . . . ? C29 C30 C31 C36 0.7(3) . . . . ? C30 C31 C32 C33 179.18(19) . . . . ? C36 C31 C32 C33 0.4(3) . . . . ? C31 C32 C33 C34 -0.1(3) . . . . ? C32 C33 C34 C35 -0.2(3) . . . . ? C33 C34 C35 C36 0.1(3) . . . . ? C34 C35 C36 C31 0.2(3) . . . . ? C34 C35 C36 C37 -179.4(2) . . . . ? C30 C31 C36 C35 -179.29(19) . . . . ? C32 C31 C36 C35 -0.4(3) . . . . ? C30 C31 C36 C37 0.4(3) . . . . ? C32 C31 C36 C37 179.21(19) . . . . ? C35 C36 C37 C38 178.4(2) . . . . ? C31 C36 C37 C38 -1.3(3) . . . . ? C35 C36 C37 C39 -1.8(3) . . . . ? C31 C36 C37 C39 178.54(19) . . . . ? C36 C37 C38 O5 -178.26(18) . . . . ? C39 C37 C38 O5 2.0(3) . . . . ? C36 C37 C38 C29 1.1(3) . . . . ? C39 C37 C38 C29 -178.65(19) . . . . ? C30 C29 C38 O5 179.25(19) . . . . ? C28 C29 C38 O5 1.6(3) . . . . ? C30 C29 C38 C37 -0.1(3) . . . . ? C28 C29 C38 C37 -177.8(2) . . . . ? C38 C37 C39 C48 -95.4(3) . . . . ? C36 C37 C39 C48 84.8(3) . . . . ? C38 C37 C39 C40 87.7(3) . . . . ? C36 C37 C39 C40 -92.1(2) . . . . ? C48 C39 C40 C41 -178.5(2) . . . . ? C37 C39 C40 C41 -1.6(3) . . . . ? C48 C39 C40 C45 -0.1(3) . . . . ? C37 C39 C40 C45 176.9(2) . . . . ? C39 C40 C41 C42 177.0(2) . . . . ? C45 C40 C41 C42 -1.5(3) . . . . ? C40 C41 C42 C43 0.9(3) . . . . ? C41 C42 C43 C44 0.8(3) . . . . ? C42 C43 C44 C45 -1.9(3) . . . . ? C43 C44 C45 C46 -177.1(2) . . . . ? C43 C44 C45 C40 1.3(3) . . . . ? C39 C40 C45 C46 0.3(3) . . . . ? C41 C40 C45 C46 178.8(2) . . . . ? C39 C40 C45 C44 -178.1(2) . . . . ? C41 C40 C45 C44 0.4(3) . . . . ? C44 C45 C46 C47 178.1(2) . . . . ? C40 C45 C46 C47 -0.3(3) . . . . ? C45 C46 C47 C48 0.1(3) . . . . ? C40 C39 C48 O6 178.38(19) . . . . ? C37 C39 C48 O6 1.4(3) . . . . ? C40 C39 C48 C47 -0.1(3) . . . . ? C37 C39 C48 C47 -177.1(2) . . . . ? C46 C47 C48 C39 0.1(3) . . . . ? C46 C47 C48 O6 -178.3(2) . . . . ? C39 C48 O6 C49 172.31(18) . . . . ? C47 C48 O6 C49 -9.2(3) . . . . ? C48 O6 C49 C50 94.4(2) . . . . ? O6 C49 C50 N2 168.69(17) . . . . ? O6 C49 C50 C54 -9.9(3) . . . . ? C54 C50 N2 C51 0.1(3) . . . . ? C49 C50 N2 C51 -178.5(2) . . . . ? C50 N2 C51 C52 0.7(4) . . . . ? N2 C51 C52 C53 -0.7(4) . . . . ? C51 C52 C53 C54 -0.2(4) . . . . ? N2 C50 C54 C53 -0.9(3) . . . . ? C49 C50 C54 C53 177.6(2) . . . . ? C52 C53 C54 C50 0.9(4) . . . . ?