# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2011 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name _publ_author_address _publ_author_footnote 'McConnell, Anna' ; ? # Address for author 1 ; ; ? # Footnote for author 1 ; 'Serpell, Christopher' ; ? # Address 2 ; ; ? # Footnote 2 ; 'Beer, P. D.' '' '' _publ_contact_author_name 'Beer, P. D.' _publ_contact_author_email paul.beer@chem.ox.ac.uk _publ_section_title ; Extending the Family of Heteroditopic Calix[4]diquinone Receptors for Cooperative AND Ion-Pair Recognition ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_name_full ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? _publ_contact_author_address ; Chemical Crystallography Laboratory, Department of Chemistry, University of Nowhere, Nowhere, NO1 4T, UK. ; _publ_contact_author_fax '+44 1865 000000' _publ_contact_author_phone '+44 1865 000000' # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' _publ_requested_journal 'Section E' # Attachment '- crystallographicdata.cif' #============================================================================== data_1 _database_code_depnum_ccdc_archive 'CCDC 839213' #TrackingRef '- crystallographicdata.cif' #============================================================================== ############################################################# # ***oxford university chemical crystallography group*** # # this structure was solved by amber thompson on 10/07/2007 ############################################################# _chemical_name_systematic ; . ; _chemical_name_common . _chemical_melting_point 'not measured' _chemical_formula_moiety 'C56 H64 N2 O10' _chemical_formula_sum 'C56 H64 N2 O10' _chemical_formula_weight 925.09 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.4651(3) _cell_length_b 13.4770(3) _cell_length_c 13.6637(4) _cell_angle_alpha 98.499(1) _cell_angle_beta 93.210(1) _cell_angle_gamma 98.034(1) _cell_volume 2420.79(10) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8440 _cell_measurement_theta_min 5.097 _cell_measurement_theta_max 27.485 _exptl_crystal_description block _exptl_crystal_colour clear_intense_yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 988 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details ; The data collection nominally covered a hemisphere of reciprocal Space, by a combination of \w and \f scans. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 17257 _diffrn_reflns_av_R_equivalents 0.0669 _diffrn_reflns_av_sigmaI/netI 0.1308 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 27.42 _reflns_number_total 10797 _reflns_number_gt 5572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+2.0538P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 10797 _refine_ls_number_parameters 632 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1720 _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2052 _refine_ls_wR_factor_gt 0.1673 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.14504(19) 0.06905(19) -0.01080(18) 0.0459(7) Uani 1 1 d . . . O2 O -0.50966(18) 0.06318(19) 0.34687(19) 0.0454(7) Uani 1 1 d . . . O3 O 0.12886(17) 0.19006(17) 0.22736(17) 0.0358(6) Uani 1 1 d . . . O4 O 0.22035(16) 0.21011(16) 0.42866(17) 0.0320(5) Uani 1 1 d . . . O5 O -0.28544(17) 0.18425(18) 0.61704(18) 0.0368(6) Uani 1 1 d . . . O6 O -0.08832(15) 0.20744(16) 0.71775(16) 0.0293(5) Uani 1 1 d . . . O7 O -0.13740(17) 0.23717(18) 0.35761(18) 0.0388(6) Uani 1 1 d . . . O8 O 0.10644(17) 0.49571(17) 0.62164(18) 0.0380(6) Uani 1 1 d . . . O9 O 0.0177(2) -0.10681(17) 0.5275(2) 0.0474(7) Uani 1 1 d . . . O10 O 0.25750(17) 0.18411(18) 0.76642(18) 0.0385(6) Uani 1 1 d . . . N1 N -0.0929(2) 0.1590(2) 0.1401(2) 0.0328(7) Uani 1 1 d . . . H1N H -0.1052 0.1723 0.2029 0.039 Uiso 1 1 calc R . . N2 N -0.3620(2) 0.1621(2) 0.3964(2) 0.0320(7) Uani 1 1 d . . . H2N H -0.2991 0.1802 0.3842 0.038 Uiso 1 1 calc R . . C1 C -0.2895(2) 0.0918(2) 0.2053(2) 0.0288(7) Uani 1 1 d . . . H1A H -0.2524 0.1521 0.2425 0.035 Uiso 1 1 calc R . . C2 C -0.3782(2) 0.0474(2) 0.2393(2) 0.0290(7) Uani 1 1 d . . . C3 C -0.4327(2) -0.0395(2) 0.1823(3) 0.0326(8) Uani 1 1 d . . . H3A H -0.4934 -0.0694 0.2051 0.039 Uiso 1 1 calc R . . C4 C -0.4012(2) -0.0839(2) 0.0933(3) 0.0329(8) Uani 1 1 d . A . C5 C -0.3118(2) -0.0378(2) 0.0624(3) 0.0325(8) Uani 1 1 d . . . H5A H -0.2887 -0.0662 0.0015 0.039 Uiso 1 1 calc R . . C6 C -0.2553(2) 0.0486(2) 0.1178(2) 0.0278(7) Uani 1 1 d . . . C7 C -0.4626(3) -0.1785(3) 0.0297(3) 0.0406(9) Uani 1 1 d . . . C8 C -0.5612(4) -0.2090(4) 0.0732(5) 0.0641(15) Uani 0.87 1 d P A 1 H8A H -0.5979 -0.2705 0.0323 0.096 Uiso 0.87 1 calc PR A 1 H8B H -0.6019 -0.1539 0.0744 0.096 Uiso 0.87 1 calc PR A 1 H8C H -0.5478 -0.2222 0.1409 0.096 Uiso 0.87 1 calc PR A 1 C9 C -0.4868(4) -0.1560(3) -0.0746(4) 0.0556(13) Uani 0.87 1 d P A 1 H9A H -0.5298 -0.2148 -0.1136 0.083 Uiso 0.87 1 calc PR A 1 H9B H -0.4242 -0.1421 -0.1068 0.083 Uiso 0.87 1 calc PR A 1 H9C H -0.5219 -0.0968 -0.0704 0.083 Uiso 0.87 1 calc PR A 1 C10 C -0.4010(4) -0.2647(3) 0.0235(4) 0.0509(13) Uani 0.87 1 d P A 1 H10A H -0.4411 -0.3264 -0.0138 0.076 Uiso 0.87 1 calc PR A 1 H10B H -0.3818 -0.2764 0.0906 0.076 Uiso 0.87 1 calc PR A 1 H10C H -0.3403 -0.2470 -0.0105 0.076 Uiso 0.87 1 calc PR A 1 C8A C -0.566(2) -0.164(2) 0.008(3) 0.0509(13) Uani 0.13 1 d P A 2 H8D H -0.5704 -0.1290 -0.0495 0.076 Uiso 0.13 1 calc PR A 2 H8E H -0.5886 -0.1227 0.0658 0.076 Uiso 0.13 1 calc PR A 2 H8F H -0.6093 -0.2299 -0.0057 0.076 Uiso 0.13 1 calc PR A 2 C9A C -0.412(2) -0.215(3) -0.058(3) 0.0641(15) Uani 0.13 1 d P A 2 H9D H -0.4054 -0.1630 -0.1015 0.096 Uiso 0.13 1 calc PR A 2 H9E H -0.4517 -0.2774 -0.0941 0.096 Uiso 0.13 1 calc PR A 2 H9F H -0.3450 -0.2284 -0.0372 0.096 Uiso 0.13 1 calc PR A 2 C10A C -0.474(3) -0.262(2) 0.100(2) 0.0556(13) Uani 0.13 1 d P A 2 H10D H -0.4980 -0.3291 0.0606 0.083 Uiso 0.13 1 calc PR A 2 H10E H -0.5224 -0.2464 0.1491 0.083 Uiso 0.13 1 calc PR A 2 H10F H -0.4086 -0.2638 0.1351 0.083 Uiso 0.13 1 calc PR A 2 C11 C -0.1602(2) 0.0934(2) 0.0764(2) 0.0314(8) Uani 1 1 d . . . C12 C -0.4217(2) 0.0914(2) 0.3317(3) 0.0311(8) Uani 1 1 d . . . C13 C -0.0006(2) 0.2081(3) 0.1069(3) 0.0330(8) Uani 1 1 d . . . H13A H 0.0127 0.2795 0.1404 0.040 Uiso 1 1 calc R . . H13B H -0.0106 0.2089 0.0347 0.040 Uiso 1 1 calc R . . C14 C 0.0904(3) 0.1586(3) 0.1263(3) 0.0358(8) Uani 1 1 d . . . H14A H 0.0719 0.0839 0.1130 0.043 Uiso 1 1 calc R . . H14B H 0.1427 0.1783 0.0817 0.043 Uiso 1 1 calc R . . C15 C 0.2089(3) 0.1383(3) 0.2547(3) 0.0389(9) Uani 1 1 d . . . H15A H 0.2498 0.1252 0.1975 0.047 Uiso 1 1 calc R . . H15B H 0.1808 0.0721 0.2726 0.047 Uiso 1 1 calc R . . C16 C 0.2747(3) 0.2001(3) 0.3411(3) 0.0374(8) Uani 1 1 d . . . H16A H 0.3343 0.1669 0.3536 0.045 Uiso 1 1 calc R . . H16B H 0.2987 0.2683 0.3251 0.045 Uiso 1 1 calc R . . C17 C -0.4000(3) 0.2096(3) 0.4869(2) 0.0335(8) Uani 1 1 d . . . H17A H -0.4725 0.2124 0.4738 0.040 Uiso 1 1 calc R . . H17B H -0.3651 0.2803 0.5041 0.040 Uiso 1 1 calc R . . C18 C -0.3864(2) 0.1557(3) 0.5744(3) 0.0352(8) Uani 1 1 d . . . H18A H -0.4339 0.1744 0.6242 0.042 Uiso 1 1 calc R . . H18B H -0.4004 0.0814 0.5527 0.042 Uiso 1 1 calc R . . C19 C -0.2620(3) 0.1300(3) 0.6953(3) 0.0364(8) Uani 1 1 d . . . H19A H -0.2397 0.0655 0.6673 0.044 Uiso 1 1 calc R . . H19B H -0.3228 0.1137 0.7309 0.044 Uiso 1 1 calc R . . C20 C -0.1806(2) 0.1925(3) 0.7661(3) 0.0345(8) Uani 1 1 d . . . H20A H -0.2008 0.2592 0.7903 0.041 Uiso 1 1 calc R . . H20B H -0.1699 0.1579 0.8240 0.041 Uiso 1 1 calc R . . C21 C 0.2781(2) 0.2778(2) 0.5059(3) 0.0290(7) Uani 1 1 d . . . C22 C 0.2737(2) 0.3807(3) 0.5135(3) 0.0316(8) Uani 1 1 d . . . C23 C 0.3410(2) 0.4477(3) 0.5825(3) 0.0349(8) Uani 1 1 d . . . H23A H 0.3390 0.5185 0.5874 0.042 Uiso 1 1 calc R . . C24 C 0.4111(2) 0.4148(3) 0.6443(3) 0.0338(8) Uani 1 1 d . . . C25 C 0.4034(2) 0.3104(2) 0.6426(3) 0.0324(8) Uani 1 1 d . . . H25A H 0.4446 0.2857 0.6895 0.039 Uiso 1 1 calc R . . C26 C 0.3376(2) 0.2409(2) 0.5750(3) 0.0310(8) Uani 1 1 d . . . C27 C 0.4959(3) 0.4880(3) 0.7072(3) 0.0428(9) Uani 1 1 d . . . C28 C 0.5938(3) 0.4731(4) 0.6608(4) 0.0700(14) Uani 1 1 d . . . H28A H 0.5907 0.4905 0.5936 0.105 Uiso 1 1 calc R . . H28B H 0.6039 0.4022 0.6575 0.105 Uiso 1 1 calc R . . H28C H 0.6499 0.5172 0.7013 0.105 Uiso 1 1 calc R . . C29 C 0.4808(4) 0.5985(3) 0.7137(5) 0.0845(18) Uani 1 1 d . . . H29A H 0.4797 0.6173 0.6470 0.127 Uiso 1 1 calc R . . H29B H 0.5362 0.6418 0.7559 0.127 Uiso 1 1 calc R . . H29C H 0.4169 0.6077 0.7422 0.127 Uiso 1 1 calc R . . C30 C 0.5109(3) 0.4639(4) 0.8128(3) 0.0618(12) Uani 1 1 d . . . H30A H 0.5286 0.3954 0.8098 0.093 Uiso 1 1 calc R . . H30B H 0.4485 0.4675 0.8459 0.093 Uiso 1 1 calc R . . H30C H 0.5652 0.5133 0.8502 0.093 Uiso 1 1 calc R . . C31 C -0.0156(2) 0.2790(2) 0.7767(2) 0.0276(7) Uani 1 1 d . . . C32 C 0.0557(2) 0.2461(2) 0.8377(2) 0.0298(7) Uani 1 1 d . . . C33 C 0.1213(2) 0.3196(2) 0.9018(2) 0.0310(7) Uani 1 1 d . . . H33A H 0.1695 0.2983 0.9444 0.037 Uiso 1 1 calc R . . C34 C 0.1191(2) 0.4239(2) 0.9059(2) 0.0311(7) Uani 1 1 d . . . C35 C 0.0527(2) 0.4518(3) 0.8367(2) 0.0326(8) Uani 1 1 d . . . H35A H 0.0530 0.5219 0.8341 0.039 Uiso 1 1 calc R . . C36 C -0.0142(2) 0.3811(2) 0.7714(2) 0.0301(7) Uani 1 1 d . . . C37 C 0.1906(3) 0.5009(3) 0.9787(3) 0.0373(8) Uani 1 1 d . . . C38 C 0.1939(3) 0.4700(3) 1.0819(3) 0.0484(10) Uani 1 1 d . . . H38A H 0.2200 0.4054 1.0790 0.073 Uiso 1 1 calc R . . H38B H 0.1259 0.4624 1.1046 0.073 Uiso 1 1 calc R . . H38C H 0.2378 0.5225 1.1283 0.073 Uiso 1 1 calc R . . C39 C 0.1617(3) 0.6077(3) 0.9874(3) 0.0505(11) Uani 1 1 d . . . H39A H 0.0928 0.6060 1.0075 0.076 Uiso 1 1 calc R . . H39B H 0.1658 0.6313 0.9231 0.076 Uiso 1 1 calc R . . H39C H 0.2080 0.6540 1.0373 0.076 Uiso 1 1 calc R . . C40 C 0.2956(3) 0.5045(3) 0.9407(4) 0.0594(12) Uani 1 1 d . . . H40A H 0.3173 0.4379 0.9390 0.089 Uiso 1 1 calc R . . H40B H 0.3430 0.5556 0.9851 0.089 Uiso 1 1 calc R . . H40C H 0.2936 0.5223 0.8737 0.089 Uiso 1 1 calc R . . C41 C -0.0767(2) 0.2879(2) 0.4231(2) 0.0295(7) Uani 1 1 d . . . C42 C 0.0273(2) 0.3196(2) 0.4027(2) 0.0290(7) Uani 1 1 d . . . H42A H 0.0503 0.2936 0.3410 0.035 Uiso 1 1 calc R . . C43 C 0.0906(2) 0.3842(2) 0.4688(2) 0.0277(7) Uani 1 1 d . . . C44 C 0.0550(2) 0.4264(2) 0.5654(2) 0.0277(7) Uani 1 1 d . . . C45 C -0.0467(2) 0.3835(2) 0.5909(2) 0.0279(7) Uani 1 1 d . . . C46 C -0.1064(2) 0.3183(2) 0.5221(2) 0.0293(7) Uani 1 1 d . . . H46A H -0.1711 0.2907 0.5386 0.035 Uiso 1 1 calc R . . C47 C 0.1979(2) 0.4194(3) 0.4484(3) 0.0340(8) Uani 1 1 d . . . H47A H 0.2106 0.4945 0.4594 0.041 Uiso 1 1 calc R . . H47B H 0.2073 0.3956 0.3779 0.041 Uiso 1 1 calc R . . C48 C -0.0784(3) 0.4159(3) 0.6928(2) 0.0325(8) Uani 1 1 d . . . H48A H -0.1497 0.3871 0.6961 0.039 Uiso 1 1 calc R . . H48B H -0.0729 0.4908 0.7058 0.039 Uiso 1 1 calc R . . C49 C 0.0718(3) -0.0356(2) 0.5808(3) 0.0363(8) Uani 1 1 d . . . C50 C 0.0387(3) 0.0105(3) 0.6755(3) 0.0362(8) Uani 1 1 d . . . H50A H -0.0257 -0.0147 0.6944 0.043 Uiso 1 1 calc R . . C51 C 0.0959(2) 0.0860(2) 0.7355(2) 0.0289(7) Uani 1 1 d . . . C52 C 0.1983(2) 0.1234(2) 0.7075(2) 0.0275(7) Uani 1 1 d . . . C53 C 0.2296(2) 0.0837(2) 0.6081(2) 0.0295(7) Uani 1 1 d . . . C54 C 0.1687(2) 0.0074(2) 0.5512(3) 0.0341(8) Uani 1 1 d . . . H54A H 0.1895 -0.0199 0.4889 0.041 Uiso 1 1 calc R . . C55 C 0.0635(3) 0.1336(2) 0.8333(2) 0.0326(8) Uani 1 1 d . . . H55A H 0.1125 0.1256 0.8874 0.039 Uiso 1 1 calc R . . H55B H -0.0027 0.0970 0.8449 0.039 Uiso 1 1 calc R . . C56 C 0.3295(2) 0.1280(2) 0.5780(3) 0.0307(7) Uani 1 1 d . . . H56A H 0.3403 0.0926 0.5116 0.037 Uiso 1 1 calc R . . H56B H 0.3833 0.1162 0.6255 0.037 Uiso 1 1 calc R . . 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 0.0474(16) 0.0533(16) 0.0314(15) -0.0041(12) 0.0132(12) -0.0043(12) O2 0.0324(14) 0.0544(16) 0.0445(16) -0.0020(13) 0.0096(12) -0.0034(12) O3 0.0355(13) 0.0418(13) 0.0302(13) 0.0012(11) 0.0013(10) 0.0114(11) O4 0.0251(12) 0.0365(13) 0.0332(13) 0.0051(10) 0.0038(10) 0.0002(10) O5 0.0276(12) 0.0440(14) 0.0387(14) 0.0130(11) -0.0014(10) -0.0011(10) O6 0.0263(12) 0.0325(12) 0.0270(12) -0.0005(10) 0.0041(10) 0.0021(10) O7 0.0322(13) 0.0443(14) 0.0342(14) -0.0041(11) -0.0017(11) -0.0013(11) O8 0.0381(13) 0.0277(12) 0.0423(15) -0.0015(11) -0.0039(11) -0.0050(10) O9 0.0522(16) 0.0299(13) 0.0523(17) -0.0040(12) -0.0088(13) -0.0043(12) O10 0.0341(13) 0.0411(14) 0.0355(14) -0.0019(11) -0.0024(11) -0.0007(11) N1 0.0294(15) 0.0418(16) 0.0251(15) 0.0041(13) 0.0041(12) -0.0015(13) N2 0.0238(14) 0.0409(16) 0.0286(15) -0.0026(13) 0.0035(12) 0.0038(12) C1 0.0264(17) 0.0287(17) 0.0285(18) 0.0007(14) -0.0027(14) 0.0002(14) C2 0.0236(16) 0.0325(17) 0.0293(18) 0.0020(14) -0.0023(14) 0.0036(14) C3 0.0263(17) 0.0302(17) 0.040(2) 0.0068(15) -0.0012(15) -0.0007(14) C4 0.0333(19) 0.0270(17) 0.035(2) -0.0018(15) -0.0059(16) 0.0031(14) C5 0.0344(19) 0.0313(17) 0.0303(19) -0.0009(15) -0.0004(15) 0.0067(15) C6 0.0288(17) 0.0279(16) 0.0260(17) 0.0023(14) -0.0003(14) 0.0044(14) C7 0.036(2) 0.0326(18) 0.047(2) -0.0065(17) -0.0053(17) 0.0006(16) C8 0.044(3) 0.052(3) 0.080(4) -0.018(3) 0.000(3) -0.018(2) C9 0.066(3) 0.043(3) 0.049(3) -0.004(2) -0.026(3) 0.003(2) C10 0.058(3) 0.029(2) 0.058(3) -0.009(2) -0.020(2) 0.010(2) C8A 0.058(3) 0.029(2) 0.058(3) -0.009(2) -0.020(2) 0.010(2) C9A 0.044(3) 0.052(3) 0.080(4) -0.018(3) 0.000(3) -0.018(2) C10A 0.066(3) 0.043(3) 0.049(3) -0.004(2) -0.026(3) 0.003(2) C11 0.0326(18) 0.0331(18) 0.0279(19) 0.0015(15) 0.0021(15) 0.0069(15) C12 0.0249(18) 0.0332(18) 0.0336(19) 0.0045(15) 0.0013(15) 0.0007(14) C13 0.0329(18) 0.0373(18) 0.0288(18) 0.0096(15) 0.0063(15) -0.0011(15) C14 0.038(2) 0.0389(19) 0.0302(19) 0.0040(15) 0.0075(15) 0.0030(16) C15 0.0337(19) 0.043(2) 0.042(2) 0.0037(17) 0.0060(16) 0.0123(16) C16 0.0275(18) 0.047(2) 0.039(2) 0.0077(17) 0.0062(16) 0.0071(16) C17 0.0291(18) 0.0380(18) 0.0323(19) -0.0030(15) 0.0060(15) 0.0087(15) C18 0.0245(17) 0.0406(19) 0.037(2) -0.0014(16) 0.0047(15) 0.0009(15) C19 0.0352(19) 0.042(2) 0.033(2) 0.0087(16) 0.0038(15) 0.0033(16) C20 0.0317(18) 0.045(2) 0.0287(19) 0.0051(16) 0.0084(15) 0.0101(16) C21 0.0190(16) 0.0300(17) 0.0366(19) 0.0064(15) 0.0025(14) -0.0029(13) C22 0.0250(17) 0.0368(18) 0.0341(19) 0.0096(15) 0.0061(14) 0.0030(14) C23 0.0300(18) 0.0310(18) 0.042(2) 0.0047(16) 0.0079(16) -0.0010(15) C24 0.0242(17) 0.0402(19) 0.036(2) 0.0056(16) 0.0059(15) 0.0005(15) C25 0.0237(17) 0.0386(19) 0.0344(19) 0.0070(15) 0.0031(14) 0.0011(14) C26 0.0229(16) 0.0348(18) 0.0356(19) 0.0044(15) 0.0075(14) 0.0046(14) C27 0.035(2) 0.048(2) 0.038(2) -0.0007(18) -0.0013(17) -0.0073(17) C28 0.038(2) 0.099(4) 0.058(3) -0.009(3) 0.009(2) -0.023(2) C29 0.078(3) 0.042(2) 0.118(5) -0.008(3) -0.040(3) -0.005(2) C30 0.054(3) 0.080(3) 0.044(3) 0.003(2) 0.003(2) -0.009(2) C31 0.0306(17) 0.0294(17) 0.0220(16) -0.0002(14) 0.0045(14) 0.0055(14) C32 0.0284(17) 0.0349(18) 0.0262(17) 0.0023(14) 0.0060(14) 0.0061(14) C33 0.0294(18) 0.0395(19) 0.0250(17) 0.0076(15) 0.0043(14) 0.0049(15) C34 0.0297(17) 0.0354(18) 0.0265(18) 0.0006(14) 0.0059(14) 0.0019(14) C35 0.0377(19) 0.0306(17) 0.0300(19) 0.0041(15) 0.0060(15) 0.0062(15) C36 0.0317(18) 0.0357(18) 0.0227(17) -0.0001(14) 0.0033(14) 0.0089(15) C37 0.0328(19) 0.0402(19) 0.036(2) -0.0024(16) 0.0023(16) 0.0029(16) C38 0.046(2) 0.056(2) 0.039(2) -0.0030(19) -0.0076(18) 0.0067(19) C39 0.053(2) 0.044(2) 0.048(2) -0.0054(19) -0.008(2) 0.0030(19) C40 0.043(2) 0.054(3) 0.075(3) -0.004(2) 0.008(2) 0.002(2) C41 0.0285(17) 0.0285(17) 0.0302(18) 0.0028(14) -0.0004(15) 0.0028(14) C42 0.0270(17) 0.0301(17) 0.0298(18) 0.0045(14) 0.0048(14) 0.0029(14) C43 0.0257(17) 0.0263(16) 0.0329(18) 0.0080(14) 0.0042(14) 0.0055(13) C44 0.0310(17) 0.0238(16) 0.0292(18) 0.0070(14) -0.0006(14) 0.0059(14) C45 0.0282(17) 0.0278(16) 0.0289(18) 0.0066(14) 0.0019(14) 0.0067(14) C46 0.0254(17) 0.0325(17) 0.0298(18) 0.0058(14) 0.0044(14) 0.0020(14) C47 0.0279(18) 0.0309(17) 0.044(2) 0.0114(16) 0.0047(15) 0.0018(14) C48 0.0357(19) 0.0340(18) 0.0290(18) 0.0052(15) 0.0019(15) 0.0091(15) C49 0.039(2) 0.0241(17) 0.044(2) 0.0047(16) -0.0046(17) 0.0020(15) C50 0.0316(19) 0.0355(19) 0.041(2) 0.0078(16) 0.0031(16) 0.0011(15) C51 0.0302(18) 0.0264(16) 0.0324(18) 0.0098(14) 0.0017(15) 0.0069(14) C52 0.0292(17) 0.0236(16) 0.0299(18) 0.0051(14) -0.0024(14) 0.0051(14) C53 0.0319(18) 0.0271(16) 0.0313(18) 0.0066(14) 0.0022(15) 0.0090(14) C54 0.0355(19) 0.0299(17) 0.035(2) -0.0001(15) 0.0011(16) 0.0057(15) C55 0.0360(19) 0.0342(18) 0.0287(18) 0.0069(15) 0.0032(15) 0.0071(15) C56 0.0270(17) 0.0335(18) 0.0325(19) 0.0053(15) 0.0039(14) 0.0073(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C11 1.224(4) . ? O2 C12 1.231(4) . ? O3 C15 1.425(4) . ? O3 C14 1.428(4) . ? O4 C21 1.405(4) . ? O4 C16 1.436(4) . ? O5 C18 1.427(4) . ? O5 C19 1.427(4) . ? O6 C31 1.399(4) . ? O6 C20 1.443(4) . ? O7 C41 1.232(4) . ? O8 C44 1.220(4) . ? O9 C49 1.233(4) . ? O10 C52 1.227(4) . ? N1 C11 1.349(4) . ? N1 C13 1.453(4) . ? N1 H1N 0.8800 . ? N2 C12 1.339(4) . ? N2 C17 1.459(4) . ? N2 H2N 0.8800 . ? C1 C6 1.383(5) . ? C1 C2 1.394(5) . ? C1 H1A 0.9500 . ? C2 C3 1.394(4) . ? C2 C12 1.500(5) . ? C3 C4 1.388(5) . ? C3 H3A 0.9500 . ? C4 C5 1.392(5) . ? C4 C7 1.537(4) . ? C5 C6 1.391(4) . ? C5 H5A 0.9500 . ? C6 C11 1.514(5) . ? C7 C8A 1.46(3) . ? C7 C9A 1.47(4) . ? C7 C10 1.514(5) . ? C7 C8 1.515(6) . ? C7 C9 1.527(6) . ? C7 C10A 1.59(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C8A H8D 0.9800 . ? C8A H8E 0.9800 . ? C8A H8F 0.9800 . ? C9A H9D 0.9800 . ? C9A H9E 0.9800 . ? C9A H9F 0.9800 . ? C10A H10D 0.9800 . ? C10A H10E 0.9800 . ? C10A H10F 0.9800 . ? C13 C14 1.504(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.503(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.503(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.493(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.386(4) . ? C21 C26 1.395(5) . ? C22 C23 1.396(5) . ? C22 C47 1.513(5) . ? C23 C24 1.393(5) . ? C23 H23A 0.9500 . ? C24 C25 1.393(5) . ? C24 C27 1.530(5) . ? C25 C26 1.391(4) . ? C25 H25A 0.9500 . ? C26 C56 1.517(5) . ? C27 C28 1.520(6) . ? C27 C29 1.522(6) . ? C27 C30 1.533(6) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 C36 1.386(4) . ? C31 C32 1.398(4) . ? C32 C33 1.392(4) . ? C32 C55 1.527(4) . ? C33 C34 1.402(5) . ? C33 H33A 0.9500 . ? C34 C35 1.393(5) . ? C34 C37 1.517(5) . ? C35 C36 1.391(4) . ? C35 H35A 0.9500 . ? C36 C48 1.510(4) . ? C37 C38 1.528(5) . ? C37 C40 1.529(5) . ? C37 C39 1.532(5) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? C41 C46 1.449(5) . ? C41 C42 1.460(4) . ? C42 C43 1.332(4) . ? C42 H42A 0.9500 . ? C43 C44 1.490(5) . ? C43 C47 1.512(5) . ? C44 C45 1.491(5) . ? C45 C46 1.332(4) . ? C45 C48 1.500(5) . ? C46 H46A 0.9500 . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 H48A 0.9900 . ? C48 H48B 0.9900 . ? C49 C54 1.454(5) . ? C49 C50 1.471(5) . ? C50 C51 1.329(5) . ? C50 H50A 0.9500 . ? C51 C52 1.491(5) . ? C51 C55 1.509(5) . ? C52 C53 1.490(5) . ? C53 C54 1.338(4) . ? C53 C56 1.498(5) . ? C54 H54A 0.9500 . ? C55 H55A 0.9900 . ? C55 H55B 0.9900 . ? C56 H56A 0.9900 . ? C56 H56B 0.9900 . ? 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 C15 O3 C14 112.8(2) . . ? C21 O4 C16 110.4(2) . . ? C18 O5 C19 113.3(3) . . ? C31 O6 C20 111.3(2) . . ? C11 N1 C13 121.2(3) . . ? C11 N1 H1N 119.4 . . ? C13 N1 H1N 119.4 . . ? C12 N2 C17 120.8(3) . . ? C12 N2 H2N 119.6 . . ? C17 N2 H2N 119.6 . . ? C6 C1 C2 120.3(3) . . ? C6 C1 H1A 119.9 . . ? C2 C1 H1A 119.9 . . ? C1 C2 C3 118.8(3) . . ? C1 C2 C12 123.4(3) . . ? C3 C2 C12 117.6(3) . . ? C4 C3 C2 122.3(3) . . ? C4 C3 H3A 118.9 . . ? C2 C3 H3A 118.9 . . ? C3 C4 C5 117.2(3) . . ? C3 C4 C7 122.1(3) . . ? C5 C4 C7 120.7(3) . . ? C6 C5 C4 122.0(3) . . ? C6 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? C1 C6 C5 119.4(3) . . ? C1 C6 C11 122.9(3) . . ? C5 C6 C11 117.6(3) . . ? C8A C7 C9A 114(2) . . ? C8A C7 C10 138.5(12) . . ? C9A C7 C10 55.7(17) . . ? C8A C7 C8 45.5(16) . . ? C9A C7 C8 136.4(12) . . ? C10 C7 C8 109.9(4) . . ? C8A C7 C9 65.1(16) . . ? C9A C7 C9 55.5(17) . . ? C10 C7 C9 109.3(4) . . ? C8 C7 C9 107.8(4) . . ? C8A C7 C4 111.5(11) . . ? C9A C7 C4 112.3(12) . . ? C10 C7 C4 108.9(3) . . ? C8 C7 C4 111.2(3) . . ? C9 C7 C4 109.6(3) . . ? C8A C7 C10A 103(2) . . ? C9A C7 C10A 110(2) . . ? C10 C7 C10A 56.8(14) . . ? C8 C7 C10A 58.5(14) . . ? C9 C7 C10A 145.0(10) . . ? C4 C7 C10A 105.3(10) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? C7 C8A H8D 109.5 . . ? C7 C8A H8E 109.5 . . ? H8D C8A H8E 109.5 . . ? C7 C8A H8F 109.5 . . ? H8D C8A H8F 109.5 . . ? H8E C8A H8F 109.5 . . ? C7 C9A H9D 109.5 . . ? C7 C9A H9E 109.5 . . ? H9D C9A H9E 109.5 . . ? C7 C9A H9F 109.5 . . ? H9D C9A H9F 109.5 . . ? H9E C9A H9F 109.5 . . ? C7 C10A H10D 109.5 . . ? C7 C10A H10E 109.5 . . ? H10D C10A H10E 109.5 . . ? C7 C10A H10F 109.5 . . ? H10D C10A H10F 109.5 . . ? H10E C10A H10F 109.5 . . ? O1 C11 N1 122.1(3) . . ? O1 C11 C6 120.8(3) . . ? N1 C11 C6 117.1(3) . . ? O2 C12 N2 121.5(3) . . ? O2 C12 C2 120.6(3) . . ? N2 C12 C2 117.9(3) . . ? N1 C13 C14 114.5(3) . . ? N1 C13 H13A 108.6 . . ? C14 C13 H13A 108.6 . . ? N1 C13 H13B 108.6 . . ? C14 C13 H13B 108.6 . . ? H13A C13 H13B 107.6 . . ? O3 C14 C13 109.3(3) . . ? O3 C14 H14A 109.8 . . ? C13 C14 H14A 109.8 . . ? O3 C14 H14B 109.8 . . ? C13 C14 H14B 109.8 . . ? H14A C14 H14B 108.3 . . ? O3 C15 C16 110.8(3) . . ? O3 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? O4 C16 C15 110.7(3) . . ? O4 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? N2 C17 C18 114.0(3) . . ? N2 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? N2 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.6 . . ? O5 C18 C17 108.8(3) . . ? O5 C18 H18A 109.9 . . ? C17 C18 H18A 109.9 . . ? O5 C18 H18B 109.9 . . ? C17 C18 H18B 109.9 . . ? H18A C18 H18B 108.3 . . ? O5 C19 C20 110.0(3) . . ? O5 C19 H19A 109.7 . . ? C20 C19 H19A 109.7 . . ? O5 C19 H19B 109.7 . . ? C20 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? O6 C20 C19 110.1(3) . . ? O6 C20 H20A 109.6 . . ? C19 C20 H20A 109.6 . . ? O6 C20 H20B 109.6 . . ? C19 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C22 C21 C26 120.6(3) . . ? C22 C21 O4 119.4(3) . . ? C26 C21 O4 120.0(3) . . ? C21 C22 C23 118.4(3) . . ? C21 C22 C47 120.7(3) . . ? C23 C22 C47 120.9(3) . . ? C24 C23 C22 122.5(3) . . ? C24 C23 H23A 118.8 . . ? C22 C23 H23A 118.8 . . ? C23 C24 C25 116.5(3) . . ? C23 C24 C27 122.3(3) . . ? C25 C24 C27 121.0(3) . . ? C26 C25 C24 122.5(3) . . ? C26 C25 H25A 118.8 . . ? C24 C25 H25A 118.8 . . ? C25 C26 C21 118.4(3) . . ? C25 C26 C56 120.6(3) . . ? C21 C26 C56 121.0(3) . . ? C28 C27 C29 109.5(4) . . ? C28 C27 C24 107.7(3) . . ? C29 C27 C24 112.9(3) . . ? C28 C27 C30 105.1(3) . . ? C29 C27 C30 108.7(4) . . ? C24 C27 C30 112.6(3) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C27 C29 H29A 109.5 . . ? C27 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C27 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C36 C31 C32 121.4(3) . . ? C36 C31 O6 119.2(3) . . ? C32 C31 O6 119.4(3) . . ? C33 C32 C31 117.8(3) . . ? C33 C32 C55 120.8(3) . . ? C31 C32 C55 121.5(3) . . ? C32 C33 C34 122.7(3) . . ? C32 C33 H33A 118.6 . . ? C34 C33 H33A 118.6 . . ? C35 C34 C33 116.6(3) . . ? C35 C34 C37 122.7(3) . . ? C33 C34 C37 120.7(3) . . ? C36 C35 C34 122.6(3) . . ? C36 C35 H35A 118.7 . . ? C34 C35 H35A 118.7 . . ? C31 C36 C35 118.4(3) . . ? C31 C36 C48 121.5(3) . . ? C35 C36 C48 119.9(3) . . ? C34 C37 C38 110.9(3) . . ? C34 C37 C40 107.7(3) . . ? C38 C37 C40 109.0(3) . . ? C34 C37 C39 112.4(3) . . ? C38 C37 C39 108.4(3) . . ? C40 C37 C39 108.3(3) . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C37 C39 H39A 109.5 . . ? C37 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C37 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C37 C40 H40A 109.5 . . ? C37 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C37 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? O7 C41 C46 121.1(3) . . ? O7 C41 C42 120.7(3) . . ? C46 C41 C42 118.2(3) . . ? C43 C42 C41 121.4(3) . . ? C43 C42 H42A 119.3 . . ? C41 C42 H42A 119.3 . . ? C42 C43 C44 119.8(3) . . ? C42 C43 C47 122.2(3) . . ? C44 C43 C47 118.0(3) . . ? O8 C44 C43 121.2(3) . . ? O8 C44 C45 120.5(3) . . ? C43 C44 C45 118.2(3) . . ? C46 C45 C44 118.8(3) . . ? C46 C45 C48 122.4(3) . . ? C44 C45 C48 118.8(3) . . ? C45 C46 C41 122.6(3) . . ? C45 C46 H46A 118.7 . . ? C41 C46 H46A 118.7 . . ? C43 C47 C22 112.5(3) . . ? C43 C47 H47A 109.1 . . ? C22 C47 H47A 109.1 . . ? C43 C47 H47B 109.1 . . ? C22 C47 H47B 109.1 . . ? H47A C47 H47B 107.8 . . ? C45 C48 C36 111.4(3) . . ? C45 C48 H48A 109.4 . . ? C36 C48 H48A 109.4 . . ? C45 C48 H48B 109.4 . . ? C36 C48 H48B 109.4 . . ? H48A C48 H48B 108.0 . . ? O9 C49 C54 121.5(3) . . ? O9 C49 C50 120.6(3) . . ? C54 C49 C50 117.9(3) . . ? C51 C50 C49 122.2(3) . . ? C51 C50 H50A 118.9 . . ? C49 C50 H50A 118.9 . . ? C50 C51 C52 119.0(3) . . ? C50 C51 C55 122.9(3) . . ? C52 C51 C55 118.1(3) . . ? O10 C52 C53 120.0(3) . . ? O10 C52 C51 120.5(3) . . ? C53 C52 C51 119.4(3) . . ? C54 C53 C52 118.3(3) . . ? C54 C53 C56 123.0(3) . . ? C52 C53 C56 118.6(3) . . ? C53 C54 C49 122.8(3) . . ? C53 C54 H54A 118.6 . . ? C49 C54 H54A 118.6 . . ? C51 C55 C32 113.1(3) . . ? C51 C55 H55A 109.0 . . ? C32 C55 H55A 109.0 . . ? C51 C55 H55B 109.0 . . ? C32 C55 H55B 109.0 . . ? H55A C55 H55B 107.8 . . ? C53 C56 C26 112.8(3) . . ? C53 C56 H56A 109.0 . . ? C26 C56 H56A 109.0 . . ? C53 C56 H56B 109.0 . . ? C26 C56 H56B 109.0 . . ? H56A C56 H56B 107.8 . . ? 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 C6 C1 C2 C3 -1.6(5) . . . . ? C6 C1 C2 C12 -178.1(3) . . . . ? C1 C2 C3 C4 0.6(5) . . . . ? C12 C2 C3 C4 177.3(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C2 C3 C4 C7 -178.8(3) . . . . ? C3 C4 C5 C6 0.5(5) . . . . ? C7 C4 C5 C6 179.2(3) . . . . ? C2 C1 C6 C5 2.0(5) . . . . ? C2 C1 C6 C11 179.5(3) . . . . ? C4 C5 C6 C1 -1.5(5) . . . . ? C4 C5 C6 C11 -179.1(3) . . . . ? C3 C4 C7 C8A 53.2(19) . . . . ? C5 C4 C7 C8A -125.4(18) . . . . ? C3 C4 C7 C9A -177.0(19) . . . . ? C5 C4 C7 C9A 4.4(19) . . . . ? C3 C4 C7 C10 -117.1(4) . . . . ? C5 C4 C7 C10 64.2(5) . . . . ? C3 C4 C7 C8 4.1(5) . . . . ? C5 C4 C7 C8 -174.5(4) . . . . ? C3 C4 C7 C9 123.3(4) . . . . ? C5 C4 C7 C9 -55.3(4) . . . . ? C3 C4 C7 C10A -57.5(15) . . . . ? C5 C4 C7 C10A 123.8(15) . . . . ? C13 N1 C11 O1 3.0(5) . . . . ? C13 N1 C11 C6 -178.4(3) . . . . ? C1 C6 C11 O1 -161.9(3) . . . . ? C5 C6 C11 O1 15.6(5) . . . . ? C1 C6 C11 N1 19.5(5) . . . . ? C5 C6 C11 N1 -163.0(3) . . . . ? C17 N2 C12 O2 -1.0(5) . . . . ? C17 N2 C12 C2 178.8(3) . . . . ? C1 C2 C12 O2 163.7(3) . . . . ? C3 C2 C12 O2 -12.8(5) . . . . ? C1 C2 C12 N2 -16.1(5) . . . . ? C3 C2 C12 N2 167.4(3) . . . . ? C11 N1 C13 C14 -98.2(4) . . . . ? C15 O3 C14 C13 173.8(3) . . . . ? N1 C13 C14 O3 -80.4(3) . . . . ? C14 O3 C15 C16 155.8(3) . . . . ? C21 O4 C16 C15 -173.0(3) . . . . ? O3 C15 C16 O4 66.0(4) . . . . ? C12 N2 C17 C18 90.5(4) . . . . ? C19 O5 C18 C17 -174.6(3) . . . . ? N2 C17 C18 O5 80.5(3) . . . . ? C18 O5 C19 C20 -152.7(3) . . . . ? C31 O6 C20 C19 170.3(3) . . . . ? O5 C19 C20 O6 -65.6(4) . . . . ? C16 O4 C21 C22 87.2(4) . . . . ? C16 O4 C21 C26 -94.1(3) . . . . ? C26 C21 C22 C23 9.4(5) . . . . ? O4 C21 C22 C23 -171.8(3) . . . . ? C26 C21 C22 C47 -170.8(3) . . . . ? O4 C21 C22 C47 7.9(5) . . . . ? C21 C22 C23 C24 -0.9(5) . . . . ? C47 C22 C23 C24 179.4(3) . . . . ? C22 C23 C24 C25 -7.3(5) . . . . ? C22 C23 C24 C27 169.6(3) . . . . ? C23 C24 C25 C26 7.4(5) . . . . ? C27 C24 C25 C26 -169.5(3) . . . . ? C24 C25 C26 C21 0.6(5) . . . . ? C24 C25 C26 C56 -178.1(3) . . . . ? C22 C21 C26 C25 -9.3(5) . . . . ? O4 C21 C26 C25 171.9(3) . . . . ? C22 C21 C26 C56 169.4(3) . . . . ? O4 C21 C26 C56 -9.3(5) . . . . ? C23 C24 C27 C28 -107.6(4) . . . . ? C25 C24 C27 C28 69.2(5) . . . . ? C23 C24 C27 C29 13.5(5) . . . . ? C25 C24 C27 C29 -169.7(4) . . . . ? C23 C24 C27 C30 137.0(4) . . . . ? C25 C24 C27 C30 -46.2(5) . . . . ? C20 O6 C31 C36 -86.3(4) . . . . ? C20 O6 C31 C32 95.4(3) . . . . ? C36 C31 C32 C33 7.3(5) . . . . ? O6 C31 C32 C33 -174.5(3) . . . . ? C36 C31 C32 C55 -171.5(3) . . . . ? O6 C31 C32 C55 6.8(5) . . . . ? C31 C32 C33 C34 -0.9(5) . . . . ? C55 C32 C33 C34 177.8(3) . . . . ? C32 C33 C34 C35 -4.9(5) . . . . ? C32 C33 C34 C37 178.6(3) . . . . ? C33 C34 C35 C36 4.8(5) . . . . ? C37 C34 C35 C36 -178.7(3) . . . . ? C32 C31 C36 C35 -7.3(5) . . . . ? O6 C31 C36 C35 174.4(3) . . . . ? C32 C31 C36 C48 168.8(3) . . . . ? O6 C31 C36 C48 -9.5(5) . . . . ? C34 C35 C36 C31 1.1(5) . . . . ? C34 C35 C36 C48 -175.1(3) . . . . ? C35 C34 C37 C38 137.6(3) . . . . ? C33 C34 C37 C38 -46.1(4) . . . . ? C35 C34 C37 C40 -103.2(4) . . . . ? C33 C34 C37 C40 73.1(4) . . . . ? C35 C34 C37 C39 16.0(5) . . . . ? C33 C34 C37 C39 -167.7(3) . . . . ? O7 C41 C42 C43 172.0(3) . . . . ? C46 C41 C42 C43 -7.7(5) . . . . ? C41 C42 C43 C44 -0.7(5) . . . . ? C41 C42 C43 C47 -178.9(3) . . . . ? C42 C43 C44 O8 -170.0(3) . . . . ? C47 C43 C44 O8 8.3(4) . . . . ? C42 C43 C44 C45 8.5(4) . . . . ? C47 C43 C44 C45 -173.2(3) . . . . ? O8 C44 C45 C46 170.5(3) . . . . ? C43 C44 C45 C46 -8.0(4) . . . . ? O8 C44 C45 C48 -8.9(4) . . . . ? C43 C44 C45 C48 172.6(3) . . . . ? C44 C45 C46 C41 -0.4(5) . . . . ? C48 C45 C46 C41 179.1(3) . . . . ? O7 C41 C46 C45 -171.4(3) . . . . ? C42 C41 C46 C45 8.3(5) . . . . ? C42 C43 C47 C22 -112.6(4) . . . . ? C44 C43 C47 C22 69.1(4) . . . . ? C21 C22 C47 C43 64.5(4) . . . . ? C23 C22 C47 C43 -115.8(4) . . . . ? C46 C45 C48 C36 115.4(3) . . . . ? C44 C45 C48 C36 -65.2(4) . . . . ? C31 C36 C48 C45 -65.4(4) . . . . ? C35 C36 C48 C45 110.7(3) . . . . ? O9 C49 C50 C51 178.7(3) . . . . ? C54 C49 C50 C51 -2.8(5) . . . . ? C49 C50 C51 C52 -2.0(5) . . . . ? C49 C50 C51 C55 -179.5(3) . . . . ? C50 C51 C52 O10 -171.0(3) . . . . ? C55 C51 C52 O10 6.6(4) . . . . ? C50 C51 C52 C53 7.0(4) . . . . ? C55 C51 C52 C53 -175.3(3) . . . . ? O10 C52 C53 C54 170.9(3) . . . . ? C51 C52 C53 C54 -7.2(4) . . . . ? O10 C52 C53 C56 -6.7(4) . . . . ? C51 C52 C53 C56 175.2(3) . . . . ? C52 C53 C54 C49 2.4(5) . . . . ? C56 C53 C54 C49 179.9(3) . . . . ? O9 C49 C54 C53 -179.0(3) . . . . ? C50 C49 C54 C53 2.6(5) . . . . ? C50 C51 C55 C32 -118.3(3) . . . . ? C52 C51 C55 C32 64.2(4) . . . . ? C33 C32 C55 C51 -113.3(3) . . . . ? C31 C32 C55 C51 65.4(4) . . . . ? C54 C53 C56 C26 122.0(3) . . . . ? C52 C53 C56 C26 -60.5(4) . . . . ? C25 C26 C56 C53 112.6(3) . . . . ? C21 C26 C56 C53 -66.1(4) . . . . ? 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 N1 H1N O7 0.88 2.25 3.123(4) 168.9 . N2 H2N O7 0.88 2.27 3.152(4) 176.3 . _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.436 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.057 #===END #============================================================================== data_3 _database_code_depnum_ccdc_archive 'CCDC 839214' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 09-04-29 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 014CJS09 _chemical_name_systematic . _chemical_melting_point . _cell_length_a 11.5030(3) _cell_length_b 13.4039(4) _cell_length_c 14.5562(5) _cell_angle_alpha 76.3517(14) _cell_angle_beta 82.0783(15) _cell_angle_gamma 81.4218(14) _cell_volume 2144.24(11) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C44 H44 Cl1 N2 O10 # Dc = 1.23 Fooo = 930.90 Mu = 1.47 M = 796.29 # Found Formula = C46.04 H42.59 Cl2.87 N2.54 O10 # Dc = 1.38 FOOO = 930.90 Mu = 2.68 M = 893.34 _chemical_formula_sum 'C46.04 H42.59 Cl2.87 N2.54 O10' _chemical_formula_moiety 'C44 H40 N2 O10, 0.96(C H Cl3), 0.54(C2 H3 N)' _chemical_compound_source . _chemical_formula_weight 893.34 _cell_measurement_reflns_used 8736 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.24 _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 930.900 _exptl_absorpt_coefficient_mu 0.268 # Sheldrick geometric approximatio 0.97 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.97 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CRYSTALMAKER (CrystalMaker, 2005)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 30051 _reflns_number_total 9701 _diffrn_reflns_av_R_equivalents 0.075 # Number of reflections with Friedels Law is 9701 # Number of reflections without Friedels Law is 15694 # Theoretical number of reflections is about 9836 _diffrn_reflns_theta_min 5.163 _diffrn_reflns_theta_max 27.484 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.010 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -14 _reflns_limit_h_max 14 _reflns_limit_k_min -16 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 3.42 _oxford_diffrn_Wilson_scale 4.85 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.60 _refine_diff_density_max 0.60 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 9699 _refine_ls_number_restraints 73 _refine_ls_number_parameters 604 _oxford_refine_ls_R_factor_ref 0.1077 _refine_ls_wR_factor_ref 0.1747 _refine_ls_goodness_of_fit_ref 1.0028 _refine_ls_shift/su_max 0.000240 # The values computed from all data _oxford_reflns_number_all 9699 _refine_ls_R_factor_all 0.1077 _refine_ls_wR_factor_all 0.1747 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6290 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_gt 0.1499 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.54P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. CrystalMaker (2005). CrystalMaker Software Limited, Yarnton England. URL: www.CrystalMaker.co.uk. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C1 C 0.7271(7) 0.7541(6) 0.7148(5) 0.0436 0.4570 Uani D . . . 1 . . Cl2 Cl 0.7667(4) 0.6732(3) 0.6337(3) 0.0509 0.4570 Uani D . . . 1 . . Cl3 Cl 0.64027(15) 0.86831(13) 0.66345(11) 0.0520 0.4570 Uani D . . . 1 . . Cl4 Cl 0.64914(18) 0.69143(14) 0.82029(12) 0.0536 0.4570 Uani D . . . 1 . . O5 O 0.75050(16) 0.36875(13) 0.04836(12) 0.0392 1.0000 Uani . . . . . . . C6 C 0.8116(2) 0.39275(19) 0.11505(18) 0.0381 1.0000 Uani . . . . . . . C7 C 0.7480(2) 0.43090(19) 0.19057(18) 0.0380 1.0000 Uani . . . . . . . C8 C 0.8115(3) 0.4529(2) 0.2571(2) 0.0426 1.0000 Uani . . . . . . . C9 C 0.9339(3) 0.4374(2) 0.2476(2) 0.0462 1.0000 Uani . . . . . . . C10 C 0.9949(2) 0.3972(2) 0.1733(2) 0.0434 1.0000 Uani . . . . . . . C11 C 0.9350(2) 0.3728(2) 0.10611(19) 0.0392 1.0000 Uani . . . . . . . C12 C 0.9999(3) 0.3179(2) 0.0308(2) 0.0442 1.0000 Uani . . . . . . . C13 C 0.9786(2) 0.2057(2) 0.05867(18) 0.0397 1.0000 Uani . . . . . . . C14 C 1.0352(2) 0.1400(2) 0.14239(18) 0.0407 1.0000 Uani . . . . . . . O15 O 1.11917(17) 0.16687(16) 0.16991(14) 0.0498 1.0000 Uani . . . . . . . C16 C 0.9886(2) 0.0407(2) 0.19095(18) 0.0393 1.0000 Uani . . . . . . . C17 C 0.9189(2) 0.0014(2) 0.14602(18) 0.0411 1.0000 Uani . . . . . . . C18 C 0.8836(2) 0.0564(2) 0.05192(18) 0.0397 1.0000 Uani . . . . . . . C19 C 0.9087(2) 0.1636(2) 0.01562(18) 0.0416 1.0000 Uani . . . . . . . O20 O 0.83063(17) 0.01442(15) 0.00605(13) 0.0463 1.0000 Uani . . . . . . . C21 C 1.0227(2) -0.0085(2) 0.28967(19) 0.0427 1.0000 Uani . . . . . . . C22 C 0.9597(2) 0.0547(2) 0.35931(18) 0.0389 1.0000 Uani . . . . . . . C23 C 0.8383(2) 0.0553(2) 0.38613(17) 0.0380 1.0000 Uani . . . . . . . O24 O 0.77797(16) -0.00802(13) 0.35126(12) 0.0397 1.0000 Uani . . . . . . . C25 C 0.7777(3) -0.1090(2) 0.41243(19) 0.0445 1.0000 Uani . . . . . . . C26 C 0.7111(3) -0.1732(2) 0.37343(19) 0.0453 1.0000 Uani . . . . . . . O27 O 0.76587(17) -0.18588(14) 0.28194(13) 0.0442 1.0000 Uani . . . . . . . C28 C 0.7272(3) -0.2701(2) 0.2546(2) 0.0475 1.0000 Uani . . . . . . . C29 C 0.7821(3) -0.2730(2) 0.15452(19) 0.0451 1.0000 Uani . . . . . . . N30 N 0.7197(2) -0.19897(17) 0.08181(15) 0.0420 1.0000 Uani . . . . . . . C31 C 0.6278(3) -0.2249(2) 0.0476(2) 0.0469 1.0000 Uani . . . . . . . O32 O 0.5943(2) -0.31065(17) 0.07646(18) 0.0691 1.0000 Uani . . . . . . . C33 C 0.5687(3) -0.1460(2) -0.02864(19) 0.0420 1.0000 Uani . . . . . . . C34 C 0.6202(3) -0.0593(2) -0.07991(19) 0.0430 1.0000 Uani . . . . . . . C35 C 0.5643(3) 0.0089(2) -0.15369(19) 0.0441 1.0000 Uani . . . . . . . C36 C 0.6181(3) 0.1019(2) -0.21298(19) 0.0461 1.0000 Uani . . . . . . . O37 O 0.5803(2) 0.14780(18) -0.28940(15) 0.0632 1.0000 Uani . . . . . . . N38 N 0.7082(2) 0.13286(18) -0.18201(16) 0.0467 1.0000 Uani . . . . . . . C39 C 0.7648(3) 0.2217(2) -0.2374(2) 0.0502 1.0000 Uani . . . . . . . C40 C 0.7038(3) 0.3239(2) -0.2194(2) 0.0510 1.0000 Uani . . . . . . . O41 O 0.73852(18) 0.33727(15) -0.13264(13) 0.0490 1.0000 Uani . . . . . . . C42 C 0.6686(3) 0.4210(2) -0.1000(2) 0.0480 1.0000 Uani . . . . . . . C43 C 0.7316(3) 0.4547(2) -0.03119(19) 0.0437 1.0000 Uani . . . . . . . C44 C 0.4585(3) -0.0118(3) -0.1764(2) 0.0506 1.0000 Uani . . . . . . . C45 C 0.4079(3) -0.0989(3) -0.1264(2) 0.0517 1.0000 Uani . . . . . . . C46 C 0.4620(3) -0.1654(2) -0.0521(2) 0.0499 1.0000 Uani . . . . . . . C47 C 0.7761(2) 0.1188(2) 0.44403(18) 0.0392 1.0000 Uani . . . . . . . C48 C 0.8391(3) 0.1821(2) 0.47661(19) 0.0451 1.0000 Uani . . . . . . . C49 C 0.9596(3) 0.1818(2) 0.4527(2) 0.0489 1.0000 Uani . . . . . . . C50 C 1.0192(3) 0.1187(2) 0.3943(2) 0.0463 1.0000 Uani . . . . . . . C51 C 0.6432(2) 0.1246(2) 0.4677(2) 0.0431 1.0000 Uani . . . . . . . C52 C 0.5859(2) 0.2341(2) 0.43801(18) 0.0395 1.0000 Uani . . . . . . . C53 C 0.6031(2) 0.2823(2) 0.33393(18) 0.0366 1.0000 Uani . . . . . . . O54 O 0.64357(18) 0.23042(15) 0.27625(13) 0.0468 1.0000 Uani . . . . . . . C55 C 0.5678(2) 0.3966(2) 0.30306(18) 0.0385 1.0000 Uani . . . . . . . C56 C 0.6142(2) 0.4447(2) 0.20267(18) 0.0398 1.0000 Uani . . . . . . . C57 C 0.5019(2) 0.4471(2) 0.36425(19) 0.0423 1.0000 Uani . . . . . . . C58 C 0.4670(2) 0.3949(2) 0.46353(19) 0.0418 1.0000 Uani . . . . . . . C59 C 0.5238(2) 0.2897(2) 0.49721(19) 0.0423 1.0000 Uani . . . . . . . O60 O 0.39336(18) 0.43798(16) 0.51558(15) 0.0517 1.0000 Uani . . . . . . . C60 C 0.9884(2) 0.5518(2) 0.4976(2) 0.0885 0.5000 Uani D U . . . . . Cl61 Cl 0.9136(3) 0.4413(2) 0.5110(2) 0.1124 0.5000 Uani D U . . . . . Cl62 Cl 0.9648(2) 0.63693(16) 0.38964(15) 0.0834 0.5000 Uani D U . . . . . Cl63 Cl 1.1410(2) 0.5139(2) 0.50342(17) 0.0874 0.5000 Uani D U . . . . . C70 C 0.6593(9) 0.7570(11) 0.7555(10) 0.1255 0.5430 Uani D U . . 2 . . C71 C 0.7270(7) 0.7068(8) 0.6857(7) 0.0787 0.5430 Uani D U . . 2 . . N72 N 0.7822(16) 0.6604(14) 0.6375(12) 0.1068 0.5430 Uani . U . . 2 . . H11 H 0.7992 0.7724 0.7306 0.0547 0.4570 Uiso R . . . 1 . . H81 H 0.7695 0.4785 0.3099 0.0534 1.0000 Uiso R . . . . . . H91 H 0.9753 0.4548 0.2932 0.0570 1.0000 Uiso R . . . . . . H101 H 1.0767 0.3856 0.1683 0.0508 1.0000 Uiso R . . . . . . H121 H 1.0841 0.3215 0.0267 0.0525 1.0000 Uiso R . . . . . . H122 H 0.9704 0.3486 -0.0324 0.0529 1.0000 Uiso R . . . . . . H171 H 0.8900 -0.0628 0.1736 0.0493 1.0000 Uiso R . . . . . . H191 H 0.8741 0.2035 -0.0393 0.0496 1.0000 Uiso R . . . . . . H212 H 1.1080 -0.0111 0.2863 0.0488 1.0000 Uiso R . . . . . . H211 H 0.9992 -0.0782 0.3082 0.0492 1.0000 Uiso R . . . . . . H251 H 0.8600 -0.1416 0.4148 0.0533 1.0000 Uiso R . . . . . . H252 H 0.7400 -0.1020 0.4754 0.0540 1.0000 Uiso R . . . . . . H261 H 0.7122 -0.2414 0.4169 0.0536 1.0000 Uiso R . . . . . . H262 H 0.6284 -0.1421 0.3693 0.0541 1.0000 Uiso R . . . . . . H281 H 0.7555 -0.3358 0.2964 0.0571 1.0000 Uiso R . . . . . . H282 H 0.6409 -0.2626 0.2568 0.0570 1.0000 Uiso R . . . . . . H292 H 0.8631 -0.2586 0.1492 0.0537 1.0000 Uiso R . . . . . . H291 H 0.7803 -0.3421 0.1448 0.0541 1.0000 Uiso R . . . . . . H341 H 0.6936 -0.0477 -0.0661 0.0517 1.0000 Uiso R . . . . . . H391 H 0.8466 0.2136 -0.2249 0.0581 1.0000 Uiso R . . . . . . H392 H 0.7615 0.2222 -0.3038 0.0586 1.0000 Uiso R . . . . . . H401 H 0.7274 0.3805 -0.2699 0.0597 1.0000 Uiso R . . . . . . H402 H 0.6180 0.3234 -0.2118 0.0598 1.0000 Uiso R . . . . . . H421 H 0.6583 0.4810 -0.1539 0.0580 1.0000 Uiso R . . . . . . H422 H 0.5902 0.4010 -0.0695 0.0576 1.0000 Uiso R . . . . . . H432 H 0.8099 0.4734 -0.0620 0.0503 1.0000 Uiso R . . . . . . H431 H 0.6839 0.5135 -0.0086 0.0505 1.0000 Uiso R . . . . . . H441 H 0.4223 0.0337 -0.2247 0.0610 1.0000 Uiso R . . . . . . H451 H 0.3362 -0.1131 -0.1446 0.0634 1.0000 Uiso R . . . . . . H461 H 0.4284 -0.2242 -0.0174 0.0613 1.0000 Uiso R . . . . . . H481 H 0.7985 0.2265 0.5148 0.0530 1.0000 Uiso R . . . . . . H491 H 1.0004 0.2249 0.4758 0.0609 1.0000 Uiso R . . . . . . H501 H 1.1016 0.1197 0.3786 0.0550 1.0000 Uiso R . . . . . . H511 H 0.6232 0.0991 0.5358 0.0498 1.0000 Uiso R . . . . . . H512 H 0.6119 0.0810 0.4324 0.0500 1.0000 Uiso R . . . . . . H562 H 0.5859 0.5181 0.1894 0.0466 1.0000 Uiso R . . . . . . H561 H 0.5856 0.4115 0.1572 0.0465 1.0000 Uiso R . . . . . . H571 H 0.4775 0.5173 0.3449 0.0506 1.0000 Uiso R . . . . . . H591 H 0.5134 0.2602 0.5628 0.0496 1.0000 Uiso R . . . . . . H381 H 0.7327 0.1013 -0.1291 0.0546 1.0000 Uiso R . . . . . . H301 H 0.7411 -0.1360 0.0613 0.0511 1.0000 Uiso R . . . . . . H701 H 0.6353 0.8268 0.7259 0.1671 0.5430 Uiso R . . . 2 . . H702 H 0.7051 0.7554 0.8055 0.1671 0.5430 Uiso R . . . 2 . . H703 H 0.5915 0.7228 0.7806 0.1671 0.5430 Uiso R . . . 2 . . H601 H 0.9583 0.5860 0.5477 0.1066 0.5000 Uiso R . . . . . . 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 0.045(4) 0.047(4) 0.041(3) -0.009(3) -0.007(3) -0.009(3) Cl2 0.0494(14) 0.0549(12) 0.0531(14) -0.0249(11) -0.0031(10) -0.0026(10) Cl3 0.0546(9) 0.0504(9) 0.0459(8) -0.0071(7) -0.0032(7) 0.0022(7) Cl4 0.0664(11) 0.0491(9) 0.0436(9) -0.0073(7) 0.0027(8) -0.0142(8) O5 0.0475(11) 0.0385(10) 0.0305(9) -0.0001(7) -0.0094(8) -0.0088(8) C6 0.0489(15) 0.0306(13) 0.0348(13) -0.0003(10) -0.0102(11) -0.0108(11) C7 0.0453(15) 0.0313(13) 0.0361(13) -0.0022(10) -0.0072(11) -0.0056(11) C8 0.0493(16) 0.0368(14) 0.0428(15) -0.0084(11) -0.0091(12) -0.0053(12) C9 0.0526(17) 0.0390(15) 0.0506(16) -0.0091(12) -0.0150(13) -0.0093(13) C10 0.0398(15) 0.0410(15) 0.0489(16) -0.0040(12) -0.0070(12) -0.0108(12) C11 0.0405(14) 0.0352(13) 0.0394(14) -0.0016(11) -0.0026(11) -0.0090(11) C12 0.0419(15) 0.0458(15) 0.0430(15) -0.0050(12) -0.0040(12) -0.0073(12) C13 0.0373(14) 0.0436(15) 0.0363(13) -0.0068(11) -0.0013(11) -0.0040(11) C14 0.0382(14) 0.0464(15) 0.0367(13) -0.0101(11) -0.0046(11) -0.0008(12) O15 0.0423(11) 0.0555(12) 0.0526(12) -0.0083(9) -0.0136(9) -0.0073(9) C16 0.0378(14) 0.0435(15) 0.0345(13) -0.0083(11) -0.0040(11) 0.0011(11) C17 0.0434(15) 0.0420(15) 0.0362(13) -0.0062(11) -0.0045(11) -0.0035(12) C18 0.0404(14) 0.0446(15) 0.0342(13) -0.0094(11) -0.0040(11) -0.0040(12) C19 0.0429(15) 0.0472(15) 0.0321(13) -0.0041(11) -0.0060(11) -0.0025(12) O20 0.0496(12) 0.0503(11) 0.0406(10) -0.0102(9) -0.0105(9) -0.0059(9) C21 0.0417(15) 0.0446(15) 0.0392(14) -0.0060(12) -0.0079(11) 0.0015(12) C22 0.0424(15) 0.0390(14) 0.0340(13) -0.0042(11) -0.0124(11) 0.0009(11) C23 0.0485(15) 0.0339(13) 0.0299(12) 0.0005(10) -0.0127(11) -0.0040(11) O24 0.0494(11) 0.0343(9) 0.0353(9) -0.0033(7) -0.0124(8) -0.0047(8) C25 0.0590(18) 0.0369(14) 0.0359(14) -0.0028(11) -0.0098(12) -0.0041(13) C26 0.0531(17) 0.0423(15) 0.0383(14) -0.0020(12) -0.0058(12) -0.0087(13) O27 0.0560(12) 0.0400(10) 0.0380(10) -0.0067(8) -0.0044(8) -0.0135(9) C28 0.0659(19) 0.0361(14) 0.0406(15) -0.0030(11) -0.0100(13) -0.0114(13) C29 0.0567(18) 0.0374(14) 0.0405(15) -0.0043(11) -0.0143(13) -0.0022(12) N30 0.0531(14) 0.0355(12) 0.0377(12) -0.0031(9) -0.0144(10) -0.0056(10) C31 0.0530(17) 0.0450(16) 0.0443(15) -0.0076(12) -0.0107(13) -0.0095(13) O32 0.0812(17) 0.0478(13) 0.0808(17) 0.0052(12) -0.0329(13) -0.0242(12) C33 0.0459(15) 0.0424(15) 0.0399(14) -0.0127(12) -0.0103(12) -0.0010(12) C34 0.0488(16) 0.0447(15) 0.0369(14) -0.0108(12) -0.0120(12) -0.0003(12) C35 0.0508(16) 0.0480(16) 0.0337(13) -0.0123(12) -0.0113(12) 0.0048(13) C36 0.0529(17) 0.0512(17) 0.0315(13) -0.0087(12) -0.0099(12) 0.0066(13) O37 0.0764(16) 0.0691(15) 0.0400(11) 0.0025(10) -0.0240(11) -0.0024(12) N38 0.0642(16) 0.0441(13) 0.0296(11) -0.0019(10) -0.0129(11) -0.0026(11) C39 0.066(2) 0.0493(17) 0.0324(14) -0.0054(12) -0.0061(13) -0.0033(14) C40 0.068(2) 0.0481(16) 0.0342(14) -0.0018(12) -0.0159(13) -0.0017(14) O41 0.0602(13) 0.0472(11) 0.0381(10) -0.0086(8) -0.0160(9) 0.0065(9) C42 0.0561(18) 0.0478(16) 0.0383(14) -0.0043(12) -0.0155(13) 0.0011(13) C43 0.0521(16) 0.0381(14) 0.0367(14) 0.0020(11) -0.0095(12) -0.0045(12) C44 0.0510(17) 0.0612(19) 0.0400(15) -0.0149(14) -0.0151(13) 0.0071(14) C45 0.0432(16) 0.069(2) 0.0482(17) -0.0229(15) -0.0124(13) 0.0011(14) C46 0.0496(17) 0.0531(18) 0.0502(17) -0.0163(14) -0.0075(13) -0.0066(14) C47 0.0480(15) 0.0354(13) 0.0310(13) -0.0020(10) -0.0088(11) 0.0006(11) C48 0.0548(18) 0.0447(16) 0.0363(14) -0.0094(12) -0.0128(12) 0.0009(13) C49 0.0525(18) 0.0523(17) 0.0467(16) -0.0130(13) -0.0195(13) -0.0053(14) C50 0.0422(15) 0.0552(17) 0.0420(15) -0.0095(13) -0.0134(12) -0.0010(13) C51 0.0482(16) 0.0386(14) 0.0380(14) -0.0009(11) -0.0028(12) -0.0049(12) C52 0.0387(14) 0.0411(14) 0.0361(13) -0.0026(11) -0.0031(11) -0.0068(11) C53 0.0396(14) 0.0369(13) 0.0339(13) -0.0061(11) -0.0069(11) -0.0064(11) O54 0.0617(13) 0.0417(11) 0.0379(10) -0.0100(8) -0.0094(9) -0.0033(9) C55 0.0378(14) 0.0402(14) 0.0371(13) -0.0054(11) -0.0080(11) -0.0047(11) C56 0.0440(15) 0.0374(14) 0.0353(13) -0.0031(11) -0.0080(11) -0.0007(11) C57 0.0462(15) 0.0374(14) 0.0410(14) -0.0049(11) -0.0072(12) -0.0014(12) C58 0.0387(14) 0.0468(15) 0.0416(14) -0.0126(12) -0.0036(12) -0.0068(12) C59 0.0452(15) 0.0477(16) 0.0322(13) -0.0041(11) -0.0023(11) -0.0085(12) O60 0.0472(12) 0.0547(12) 0.0518(12) -0.0156(10) 0.0024(9) -0.0028(9) C60 0.0839(19) 0.091(2) 0.089(2) -0.0248(19) -0.026(2) 0.0173(19) Cl61 0.107(2) 0.0991(18) 0.119(2) -0.0150(15) 0.0048(18) -0.0041(15) Cl62 0.0997(14) 0.0739(12) 0.0830(12) -0.0285(10) -0.0389(11) 0.0140(10) Cl63 0.0817(14) 0.1089(17) 0.0764(13) -0.0446(12) -0.0317(11) 0.0332(12) C70 0.058(5) 0.189(11) 0.179(10) -0.140(9) -0.007(6) -0.019(6) C71 0.062(5) 0.093(6) 0.102(6) -0.055(5) -0.007(4) -0.021(4) N72 0.083(9) 0.146(11) 0.117(9) -0.085(8) -0.010(6) -0.007(7) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.4634(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . Cl2 . 1.758(11) yes C1 . Cl3 . 1.763(8) yes C1 . Cl4 . 1.762(7) yes C1 . H11 . 0.969 no O5 . C6 . 1.394(3) yes O5 . C43 . 1.442(3) yes C6 . C7 . 1.392(4) yes C6 . C11 . 1.398(4) yes C7 . C8 . 1.397(4) yes C7 . C56 . 1.514(4) yes C8 . C9 . 1.384(4) yes C8 . H81 . 0.957 no C9 . C10 . 1.380(4) yes C9 . H91 . 0.957 no C10 . C11 . 1.393(4) yes C10 . H101 . 0.926 no C11 . C12 . 1.514(4) yes C12 . C13 . 1.510(4) yes C12 . H121 . 0.971 no C12 . H122 . 0.999 no C13 . C14 . 1.492(4) yes C13 . C19 . 1.341(4) yes C14 . O15 . 1.226(3) yes C14 . C16 . 1.491(4) yes C16 . C17 . 1.335(4) yes C16 . C21 . 1.512(4) yes C17 . C18 . 1.474(4) yes C17 . H171 . 0.946 no C18 . C19 . 1.466(4) yes C18 . O20 . 1.235(3) yes C19 . H191 . 0.951 no C21 . C22 . 1.513(4) yes C21 . H212 . 0.972 no C21 . H211 . 0.977 no C22 . C23 . 1.397(4) yes C22 . C50 . 1.394(4) yes C23 . O24 . 1.392(3) yes C23 . C47 . 1.392(4) yes O24 . C25 . 1.434(3) yes C25 . C26 . 1.482(4) yes C25 . H251 . 0.984 no C25 . H252 . 0.978 no C26 . O27 . 1.430(3) yes C26 . H261 . 0.982 no C26 . H262 . 0.984 no O27 . C28 . 1.428(3) yes C28 . C29 . 1.512(4) yes C28 . H281 . 0.985 no C28 . H282 . 0.980 no C29 . N30 . 1.457(3) yes C29 . H292 . 0.968 no C29 . H291 . 0.973 no N30 . C31 . 1.350(4) yes N30 . H301 . 0.886 no C31 . O32 . 1.227(3) yes C31 . C33 . 1.500(4) yes C33 . C34 . 1.390(4) yes C33 . C46 . 1.394(4) yes C34 . C35 . 1.398(4) yes C34 . H341 . 0.937 no C35 . C36 . 1.502(4) yes C35 . C44 . 1.386(4) yes C36 . O37 . 1.239(3) yes C36 . N38 . 1.339(4) yes N38 . C39 . 1.458(4) yes N38 . H381 . 0.850 no C39 . C40 . 1.506(4) yes C39 . H391 . 0.968 no C39 . H392 . 0.970 no C40 . O41 . 1.433(3) yes C40 . H401 . 0.967 no C40 . H402 . 0.978 no O41 . C42 . 1.417(4) yes C42 . C43 . 1.499(4) yes C42 . H421 . 0.987 no C42 . H422 . 0.993 no C43 . H432 . 0.989 no C43 . H431 . 0.987 no C44 . C45 . 1.385(5) yes C44 . H441 . 0.919 no C45 . C46 . 1.385(4) yes C45 . H451 . 0.957 no C46 . H461 . 0.935 no C47 . C48 . 1.391(4) yes C47 . C51 . 1.515(4) yes C48 . C49 . 1.381(4) yes C48 . H481 . 0.940 no C49 . C50 . 1.383(4) yes C49 . H491 . 0.941 no C50 . H501 . 0.944 no C51 . C52 . 1.505(4) yes C51 . H511 . 0.977 no C51 . H512 . 0.996 no C52 . C53 . 1.498(3) yes C52 . C59 . 1.335(4) yes C53 . O54 . 1.215(3) yes C53 . C55 . 1.502(4) yes C55 . C56 . 1.509(4) yes C55 . C57 . 1.331(4) yes C56 . H562 . 0.971 no C56 . H561 . 0.994 no C57 . C58 . 1.478(4) yes C57 . H571 . 0.928 no C58 . C59 . 1.464(4) yes C58 . O60 . 1.228(3) yes C59 . H591 . 0.941 no C60 . Cl63 2_766 1.843(5) yes C60 . C60 2_766 1.363(5) yes C60 . Cl61 2_766 1.131(5) yes C60 . Cl61 . 1.781(4) yes C60 . Cl62 . 1.739(3) yes C60 . Cl63 . 1.761(4) yes C60 . H601 . 0.950 no Cl61 . Cl62 2_766 2.133(4) yes Cl61 . H601 2_766 1.635 no Cl62 . Cl63 2_766 2.592(4) yes C70 . C71 . 1.427(8) yes C70 . H701 . 0.950 no C70 . H702 . 0.950 no C70 . H703 . 0.950 no C71 . N72 . 1.116(17) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl2 . C1 . Cl3 . 110.5(4) yes Cl2 . C1 . Cl4 . 111.6(4) yes Cl3 . C1 . Cl4 . 109.4(5) yes Cl2 . C1 . H11 . 108.0 no Cl3 . C1 . H11 . 108.8 no Cl4 . C1 . H11 . 108.5 no C6 . O5 . C43 . 112.24(19) yes O5 . C6 . C7 . 119.2(2) yes O5 . C6 . C11 . 118.6(2) yes C7 . C6 . C11 . 122.2(2) yes C6 . C7 . C8 . 117.9(2) yes C6 . C7 . C56 . 121.3(2) yes C8 . C7 . C56 . 120.7(2) yes C7 . C8 . C9 . 120.7(3) yes C7 . C8 . H81 . 119.2 no C9 . C8 . H81 . 120.0 no C8 . C9 . C10 . 120.3(3) yes C8 . C9 . H91 . 119.0 no C10 . C9 . H91 . 120.7 no C9 . C10 . C11 . 120.9(3) yes C9 . C10 . H101 . 119.6 no C11 . C10 . H101 . 119.5 no C6 . C11 . C10 . 117.9(3) yes C6 . C11 . C12 . 120.6(2) yes C10 . C11 . C12 . 121.2(2) yes C11 . C12 . C13 . 108.8(2) yes C11 . C12 . H121 . 109.8 no C13 . C12 . H121 . 108.8 no C11 . C12 . H122 . 111.2 no C13 . C12 . H122 . 108.2 no H121 . C12 . H122 . 110.1 no C12 . C13 . C14 . 117.0(2) yes C12 . C13 . C19 . 124.1(2) yes C14 . C13 . C19 . 118.7(2) yes C13 . C14 . O15 . 120.4(2) yes C13 . C14 . C16 . 118.7(2) yes O15 . C14 . C16 . 120.8(2) yes C14 . C16 . C17 . 118.8(2) yes C14 . C16 . C21 . 117.2(2) yes C17 . C16 . C21 . 124.0(3) yes C16 . C17 . C18 . 121.2(3) yes C16 . C17 . H171 . 121.2 no C18 . C17 . H171 . 117.6 no C17 . C18 . C19 . 118.5(2) yes C17 . C18 . O20 . 120.8(2) yes C19 . C18 . O20 . 120.7(2) yes C18 . C19 . C13 . 121.1(2) yes C18 . C19 . H191 . 118.8 no C13 . C19 . H191 . 120.0 no C16 . C21 . C22 . 109.8(2) yes C16 . C21 . H212 . 106.9 no C22 . C21 . H212 . 111.4 no C16 . C21 . H211 . 108.7 no C22 . C21 . H211 . 109.3 no H212 . C21 . H211 . 110.6 no C21 . C22 . C23 . 120.8(2) yes C21 . C22 . C50 . 121.3(3) yes C23 . C22 . C50 . 117.8(3) yes C22 . C23 . O24 . 118.3(2) yes C22 . C23 . C47 . 122.2(2) yes O24 . C23 . C47 . 119.5(2) yes C23 . O24 . C25 . 111.75(18) yes O24 . C25 . C26 . 109.9(2) yes O24 . C25 . H251 . 108.2 no C26 . C25 . H251 . 108.7 no O24 . C25 . H252 . 108.8 no C26 . C25 . H252 . 109.6 no H251 . C25 . H252 . 111.6 no C25 . C26 . O27 . 110.5(2) yes C25 . C26 . H261 . 107.9 no O27 . C26 . H261 . 108.8 no C25 . C26 . H262 . 110.7 no O27 . C26 . H262 . 110.2 no H261 . C26 . H262 . 108.7 no C26 . O27 . C28 . 112.0(2) yes O27 . C28 . C29 . 108.6(2) yes O27 . C28 . H281 . 109.8 no C29 . C28 . H281 . 107.5 no O27 . C28 . H282 . 111.4 no C29 . C28 . H282 . 109.5 no H281 . C28 . H282 . 110.0 no C28 . C29 . N30 . 113.2(2) yes C28 . C29 . H292 . 107.8 no N30 . C29 . H292 . 109.5 no C28 . C29 . H291 . 108.0 no N30 . C29 . H291 . 108.2 no H292 . C29 . H291 . 110.1 no C29 . N30 . C31 . 120.4(2) yes C29 . N30 . H301 . 119.5 no C31 . N30 . H301 . 120.1 no N30 . C31 . O32 . 121.5(3) yes N30 . C31 . C33 . 117.9(2) yes O32 . C31 . C33 . 120.7(3) yes C31 . C33 . C34 . 122.5(3) yes C31 . C33 . C46 . 117.7(3) yes C34 . C33 . C46 . 119.7(3) yes C33 . C34 . C35 . 120.2(3) yes C33 . C34 . H341 . 119.9 no C35 . C34 . H341 . 119.9 no C34 . C35 . C36 . 122.1(3) yes C34 . C35 . C44 . 119.4(3) yes C36 . C35 . C44 . 118.4(2) yes C35 . C36 . O37 . 120.3(3) yes C35 . C36 . N38 . 118.6(2) yes O37 . C36 . N38 . 121.1(3) yes C36 . N38 . C39 . 120.9(2) yes C36 . N38 . H381 . 120.3 no C39 . N38 . H381 . 118.8 no N38 . C39 . C40 . 113.8(3) yes N38 . C39 . H391 . 109.7 no C40 . C39 . H391 . 109.6 no N38 . C39 . H392 . 106.5 no C40 . C39 . H392 . 107.8 no H391 . C39 . H392 . 109.4 no C39 . C40 . O41 . 108.1(2) yes C39 . C40 . H401 . 111.0 no O41 . C40 . H401 . 108.1 no C39 . C40 . H402 . 109.9 no O41 . C40 . H402 . 108.5 no H401 . C40 . H402 . 111.1 no C40 . O41 . C42 . 112.1(2) yes O41 . C42 . C43 . 109.8(2) yes O41 . C42 . H421 . 109.7 no C43 . C42 . H421 . 106.3 no O41 . C42 . H422 . 110.6 no C43 . C42 . H422 . 110.2 no H421 . C42 . H422 . 110.1 no C42 . C43 . O5 . 108.4(2) yes C42 . C43 . H432 . 109.5 no O5 . C43 . H432 . 107.9 no C42 . C43 . H431 . 110.4 no O5 . C43 . H431 . 109.6 no H432 . C43 . H431 . 110.9 no C35 . C44 . C45 . 120.6(3) yes C35 . C44 . H441 . 118.8 no C45 . C44 . H441 . 120.6 no C44 . C45 . C46 . 120.0(3) yes C44 . C45 . H451 . 119.3 no C46 . C45 . H451 . 120.7 no C33 . C46 . C45 . 120.2(3) yes C33 . C46 . H461 . 119.0 no C45 . C46 . H461 . 120.9 no C23 . C47 . C48 . 117.9(3) yes C23 . C47 . C51 . 122.1(2) yes C48 . C47 . C51 . 119.9(3) yes C47 . C48 . C49 . 121.2(3) yes C47 . C48 . H481 . 119.2 no C49 . C48 . H481 . 119.5 no C48 . C49 . C50 . 119.8(3) yes C48 . C49 . H491 . 119.8 no C50 . C49 . H491 . 120.4 no C22 . C50 . C49 . 121.0(3) yes C22 . C50 . H501 . 120.4 no C49 . C50 . H501 . 118.6 no C47 . C51 . C52 . 110.6(2) yes C47 . C51 . H511 . 110.3 no C52 . C51 . H511 . 109.6 no C47 . C51 . H512 . 109.0 no C52 . C51 . H512 . 108.3 no H511 . C51 . H512 . 109.0 no C51 . C52 . C53 . 116.0(2) yes C51 . C52 . C59 . 124.9(2) yes C53 . C52 . C59 . 119.2(2) yes C52 . C53 . O54 . 121.1(2) yes C52 . C53 . C55 . 117.9(2) yes O54 . C53 . C55 . 121.0(2) yes C53 . C55 . C56 . 115.1(2) yes C53 . C55 . C57 . 119.3(2) yes C56 . C55 . C57 . 125.6(2) yes C7 . C56 . C55 . 110.7(2) yes C7 . C56 . H562 . 109.0 no C55 . C56 . H562 . 108.8 no C7 . C56 . H561 . 108.8 no C55 . C56 . H561 . 109.8 no H562 . C56 . H561 . 109.7 no C55 . C57 . C58 . 121.9(3) yes C55 . C57 . H571 . 119.7 no C58 . C57 . H571 . 118.4 no C57 . C58 . C59 . 117.2(2) yes C57 . C58 . O60 . 121.4(3) yes C59 . C58 . O60 . 121.4(2) yes C58 . C59 . C52 . 122.3(2) yes C58 . C59 . H591 . 118.1 no C52 . C59 . H591 . 119.6 no Cl63 2_766 C60 . C60 2_766 64.6(3) yes Cl63 2_766 C60 . Cl61 2_766 154.1(3) yes C60 2_766 C60 . Cl61 2_766 90.6(3) yes Cl61 2_766 C60 . Cl61 . 130.1(2) yes Cl63 2_766 C60 . Cl62 . 92.65(15) yes C60 2_766 C60 . Cl62 . 120.2(3) yes Cl61 2_766 C60 . Cl62 . 93.6(3) yes Cl61 . C60 . Cl62 . 110.17(10) yes Cl63 2_766 C60 . Cl63 . 135.64(15) yes C60 2_766 C60 . Cl63 . 71.1(2) yes Cl61 . C60 . Cl63 . 110.12(10) yes Cl62 . C60 . Cl63 . 109.91(10) yes Cl63 2_766 C60 . H601 . 98.5 no C60 2_766 C60 . H601 . 128.0 no Cl61 2_766 C60 . H601 . 103.3 no Cl61 . C60 . H601 . 109.0 no Cl62 . C60 . H601 . 108.8 no Cl63 . C60 . H601 . 108.8 no Cl62 2_766 Cl61 . C60 . 86.55(13) yes Cl62 2_766 Cl61 . H601 2_766 71.3 no C60 . Cl61 . H601 2_766 75.2 no Cl62 2_766 Cl61 . C60 2_766 54.5(2) yes C60 . Cl61 . C60 2_766 49.9(2) yes Cl61 2_766 Cl62 . Cl63 2_766 75.11(11) yes C60 . Cl62 . Cl63 2_766 45.27(10) yes C60 . Cl63 . Cl62 2_766 73.74(9) yes C71 . C70 . H701 . 108.7 no C71 . C70 . H702 . 110.6 no H701 . C70 . H702 . 109.5 no C71 . C70 . H703 . 109.1 no H701 . C70 . H703 . 109.5 no H702 . C70 . H703 . 109.5 no C70 . C71 . N72 . 173.9(14) yes loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C1 . H11 . O15 2_766 146 0.97 2.19 3.046(5) yes C17 . H171 . O27 . 158 0.95 2.47 3.365(5) yes C19 . H191 . O41 . 158 0.95 2.47 3.368(5) yes C34 . H341 . O20 . 159 0.94 2.35 3.246(5) yes C56 . H562 . O32 1_565 147 0.97 2.49 3.351(5) yes C59 . H591 . O37 1_556 153 0.94 2.46 3.330(5) yes N38 . H381 . O20 . 171 0.85 2.37 3.216(5) yes N30 . H301 . O20 . 170 0.89 2.32 3.200(5) yes C70 . H702 . O15 2_766 138 0.95 2.51 3.282(5) yes C60 . H601 . N72 . 147 0.95 2.47 3.307(5) yes #===END #============================================================================== data_12 _database_code_depnum_ccdc_archive 'CCDC 839215' #TrackingRef '- crystallographicdata.cif' #============================================================================== _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 12.5858(2) _cell_length_b 20.2654(2) _cell_length_c 17.1345(2) _cell_angle_alpha 90 _cell_angle_beta 99.8495(5) _cell_angle_gamma 90 _cell_volume 4305.85(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C52 H46 N2 O10' _chemical_formula_moiety 'C52 H46 N2 O10' _chemical_compound_source 'synthesis as described' _chemical_formula_weight 858.94 _cell_measurement_reflns_used 49220 _cell_measurement_theta_min 5 _cell_measurement_theta_max 28 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.28 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_max 0.42 _exptl_crystal_density_diffrn 1.325 _exptl_crystal_density_meas ? _exptl_crystal_F_000 1808 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _exptl_crystal_thermal_history ; The material was crystallised at ambient temperature. A suitable crystal was cooled rapidly to 150K for single-crystal X-ray diffraction analysis. ; _diffrn_reflns_number 49220 _reflns_number_total 9778 #10052 unique reflections including absences _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_theta_min 5.108 _diffrn_reflns_theta_max 27.465 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.465 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -16 _reflns_limit_h_max 16 _reflns_limit_k_min 0 _reflns_limit_k_max 26 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _atom_sites_solution_primary direct _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.17 _refine_diff_density_max 0.20 _refine_ls_number_reflns 5775 _refine_ls_number_restraints 0 _refine_ls_number_parameters 585 #_refine_ls_R_factor_ref 0.0350 _refine_ls_wR_factor_ref 0.0393 _refine_ls_goodness_of_fit_ref 1.1083 #_reflns_number_all 9778 _refine_ls_R_factor_all 0.0757 _refine_ls_wR_factor_all 0.0718 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 5775 _refine_ls_R_factor_gt 0.0350 _refine_ls_wR_factor_gt 0.0393 _refine_ls_shift/su_max 0.000527 _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.515 0.205 0.263 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.37107(13) 0.33858(7) 0.33565(9) 0.0238 1.0000 Uani . . . . . . C2 C 0.46942(12) 0.37209(8) 0.35008(9) 0.0249 1.0000 Uani . . . . . . C3 C 0.48739(14) 0.41447(9) 0.41488(10) 0.0323 1.0000 Uani . . . . . . C4 C 0.40995(15) 0.42439(9) 0.46223(11) 0.0362 1.0000 Uani . . . . . . C5 C 0.31095(14) 0.39326(9) 0.44374(10) 0.0325 1.0000 Uani . . . . . . C6 C 0.28951(13) 0.34960(8) 0.38044(9) 0.0253 1.0000 Uani . . . . . . C7 C 0.17899(13) 0.31812(8) 0.35874(10) 0.0287 1.0000 Uani . . . . . . C8 C 0.09671(12) 0.38395(8) 0.23708(9) 0.0241 1.0000 Uani . . . . . . C9 C 0.09813(12) 0.36734(8) 0.31671(10) 0.0249 1.0000 Uani . . . . . . C10 C 0.02633(13) 0.39913(8) 0.35754(10) 0.0281 1.0000 Uani . . . . . . C11 C -0.04423(13) 0.44666(8) 0.32119(10) 0.0283 1.0000 Uani . . . . . . C12 C -0.04262(12) 0.46358(8) 0.24303(10) 0.0276 1.0000 Uani . . . . . . C13 C 0.02740(12) 0.43273(8) 0.19992(9) 0.0245 1.0000 Uani . . . . . . C14 C 0.03074(12) 0.45195(8) 0.11480(10) 0.0267 1.0000 Uani . . . . . . C15 C 0.11817(12) 0.50263(8) 0.10964(9) 0.0239 1.0000 Uani . . . . . . C16 C 0.10853(13) 0.56667(8) 0.13720(10) 0.0288 1.0000 Uani . . . . . . C17 C 0.19115(15) 0.61214(8) 0.13851(11) 0.0329 1.0000 Uani . . . . . . C18 C 0.28580(14) 0.59394(8) 0.11341(10) 0.0301 1.0000 Uani . . . . . . C19 C 0.29876(13) 0.53043(8) 0.08529(9) 0.0246 1.0000 Uani . . . . . . C20 C 0.21313(12) 0.48634(7) 0.08244(9) 0.0221 1.0000 Uani . . . . . . C21 C 0.40536(13) 0.50961(8) 0.06244(10) 0.0261 1.0000 Uani . . . . . . C22 C 0.48537(12) 0.43908(7) 0.18077(9) 0.0227 1.0000 Uani . . . . . . C23 C 0.49094(12) 0.49518(8) 0.13397(9) 0.0245 1.0000 Uani . . . . . . C24 C 0.57757(13) 0.53798(8) 0.15534(10) 0.0282 1.0000 Uani . . . . . . C25 C 0.65605(13) 0.52642(9) 0.22087(11) 0.0322 1.0000 Uani . . . . . . C26 C 0.64712(13) 0.47132(8) 0.26743(10) 0.0291 1.0000 Uani . . . . . . C27 C 0.56299(12) 0.42686(8) 0.24820(9) 0.0244 1.0000 Uani . . . . . . C28 C 0.55363(12) 0.36535(8) 0.29683(10) 0.0266 1.0000 Uani . . . . . . O1 O 0.34948(9) 0.29472(5) 0.27244(6) 0.0249 1.0000 Uani . . . . . . C29 C 0.39505(13) 0.22975(8) 0.28943(10) 0.0262 1.0000 Uani . . . . . . C30 C 0.36596(13) 0.18953(8) 0.21606(10) 0.0291 1.0000 Uani . . . . . . O2 O 0.25413(9) 0.17402(6) 0.20660(7) 0.0301 1.0000 Uani . . . . . . C31 C 0.21735(15) 0.14471(9) 0.13204(11) 0.0356 1.0000 Uani . . . . . . C32 C 0.10122(16) 0.12502(9) 0.12878(12) 0.0414 1.0000 Uani . . . . . . N1 N 0.03165(12) 0.18127(7) 0.13498(9) 0.0329 1.0000 Uani . . . . . . C33 C -0.00518(14) 0.22358(9) 0.07226(10) 0.0319 1.0000 Uani . . . . . . C34 C -0.07943(13) 0.27054(9) 0.10225(11) 0.0322 1.0000 Uani . . . . . . C35 C -0.14063(15) 0.32086(10) 0.06354(13) 0.0443 1.0000 Uani . . . . . . C36 C -0.20684(16) 0.35510(11) 0.10614(18) 0.0565 1.0000 Uani . . . . . . C37 C -0.21142(18) 0.33925(12) 0.18403(19) 0.0628 1.0000 Uani . . . . . . C38 C -0.14886(17) 0.28877(11) 0.22293(14) 0.0519 1.0000 Uani . . . . . . C39 C -0.08248(14) 0.25471(9) 0.18038(11) 0.0365 1.0000 Uani . . . . . . C40 C -0.00952(16) 0.19806(10) 0.20304(11) 0.0387 1.0000 Uani . . . . . . O3 O 0.02026(11) 0.21979(7) 0.00751(8) 0.0452 1.0000 Uani . . . . . . O4 O 0.01234(14) 0.16948(8) 0.26596(9) 0.0562 1.0000 Uani . . . . . . O5 O 0.16033(10) 0.35279(6) 0.19160(7) 0.0304 1.0000 Uani . . . . . . O6 O 0.22807(8) 0.42169(5) 0.05851(6) 0.0235 1.0000 Uani . . . . . . C41 C 0.20100(13) 0.40764(8) -0.02453(10) 0.0277 1.0000 Uani . . . . . . C42 C 0.24632(13) 0.34032(8) -0.03578(10) 0.0303 1.0000 Uani . . . . . . O7 O 0.36133(9) 0.34495(5) -0.01876(7) 0.0288 1.0000 Uani . . . . . . C43 C 0.41415(13) 0.28545(8) 0.00818(9) 0.0269 1.0000 Uani . . . . . . C44 C 0.53223(14) 0.30145(8) 0.03267(12) 0.0346 1.0000 Uani . . . . . . N2 N 0.59907(11) 0.24231(7) 0.04377(9) 0.0310 1.0000 Uani . . . . . . C45 C 0.61787(13) 0.20513(9) 0.11299(11) 0.0325 1.0000 Uani . . . . . . C46 C 0.69226(13) 0.15114(8) 0.09831(11) 0.0306 1.0000 Uani . . . . . . C47 C 0.73419(16) 0.09927(10) 0.14626(12) 0.0422 1.0000 Uani . . . . . . C48 C 0.80416(17) 0.05650(10) 0.11667(14) 0.0493 1.0000 Uani . . . . . . C49 C 0.83071(16) 0.06619(10) 0.04241(14) 0.0468 1.0000 Uani . . . . . . C50 C 0.78896(14) 0.11872(9) -0.00574(12) 0.0382 1.0000 Uani . . . . . . C51 C 0.71841(13) 0.16060(8) 0.02397(10) 0.0290 1.0000 Uani . . . . . . C52 C 0.65948(13) 0.21967(8) -0.01219(10) 0.0291 1.0000 Uani . . . . . . O8 O 0.58043(11) 0.21685(7) 0.17188(8) 0.0449 1.0000 Uani . . . . . . O9 O 0.66100(11) 0.24517(6) -0.07586(8) 0.0381 1.0000 Uani . . . . . . O10 O 0.40703(9) 0.39249(5) 0.16414(7) 0.0270 1.0000 Uani . . . . . . H1 H 0.212(2) 0.3304(12) 0.2203(15) 0.060(7) 1.0000 Uiso . . . . . . H2 H 0.356(2) 0.4027(12) 0.1210(15) 0.061(7) 1.0000 Uiso . . . . . . H31 H 0.5578 0.4383 0.4276 0.0380 1.0000 Uiso . . . . . . H41 H 0.4255 0.4539 0.5096 0.0430 1.0000 Uiso . . . . . . H51 H 0.2540 0.4023 0.4765 0.0396 1.0000 Uiso . . . . . . H71 H 0.1544 0.3026 0.4081 0.0350 1.0000 Uiso . . . . . . H72 H 0.1838 0.2796 0.3230 0.0350 1.0000 Uiso . . . . . . H101 H 0.0257 0.3874 0.4142 0.0342 1.0000 Uiso . . . . . . H111 H -0.0960 0.4686 0.3511 0.0346 1.0000 Uiso . . . . . . H121 H -0.0926 0.4986 0.2172 0.0331 1.0000 Uiso . . . . . . H141 H -0.0407 0.4710 0.0908 0.0318 1.0000 Uiso . . . . . . H142 H 0.0452 0.4116 0.0847 0.0318 1.0000 Uiso . . . . . . H161 H 0.0410 0.5801 0.1563 0.0351 1.0000 Uiso . . . . . . H171 H 0.1823 0.6581 0.1576 0.0404 1.0000 Uiso . . . . . . H181 H 0.3456 0.6267 0.1155 0.0367 1.0000 Uiso . . . . . . H211 H 0.4316 0.5460 0.0312 0.0320 1.0000 Uiso . . . . . . H212 H 0.3932 0.4689 0.0291 0.0320 1.0000 Uiso . . . . . . H241 H 0.5832 0.5782 0.1224 0.0348 1.0000 Uiso . . . . . . H251 H 0.7184 0.5573 0.2345 0.0389 1.0000 Uiso . . . . . . H261 H 0.7025 0.4635 0.3158 0.0347 1.0000 Uiso . . . . . . H281 H 0.6252 0.3564 0.3306 0.0318 1.0000 Uiso . . . . . . H282 H 0.5334 0.3274 0.2600 0.0318 1.0000 Uiso . . . . . . H291 H 0.4753 0.2329 0.3044 0.0316 1.0000 Uiso . . . . . . H292 H 0.3645 0.2092 0.3338 0.0316 1.0000 Uiso . . . . . . H301 H 0.3807 0.2153 0.1693 0.0356 1.0000 Uiso . . . . . . H302 H 0.4094 0.1479 0.2209 0.0356 1.0000 Uiso . . . . . . H311 H 0.2231 0.1770 0.0889 0.0416 1.0000 Uiso . . . . . . H312 H 0.2617 0.1048 0.1254 0.0416 1.0000 Uiso . . . . . . H321 H 0.0966 0.0941 0.1736 0.0481 1.0000 Uiso . . . . . . H322 H 0.0755 0.1021 0.0773 0.0481 1.0000 Uiso . . . . . . H351 H -0.1374 0.3321 0.0072 0.0515 1.0000 Uiso . . . . . . H361 H -0.2523 0.3920 0.0801 0.0667 1.0000 Uiso . . . . . . H371 H -0.2607 0.3646 0.2129 0.0775 1.0000 Uiso . . . . . . H381 H -0.1517 0.2775 0.2794 0.0650 1.0000 Uiso . . . . . . H411 H 0.2340 0.4412 -0.0558 0.0328 1.0000 Uiso . . . . . . H412 H 0.1209 0.4076 -0.0416 0.0328 1.0000 Uiso . . . . . . H421 H 0.2227 0.3254 -0.0917 0.0361 1.0000 Uiso . . . . . . H422 H 0.2206 0.3081 0.0011 0.0361 1.0000 Uiso . . . . . . H431 H 0.4043 0.2520 -0.0353 0.0319 1.0000 Uiso . . . . . . H432 H 0.3842 0.2678 0.0544 0.0319 1.0000 Uiso . . . . . . H441 H 0.5559 0.3293 -0.0094 0.0417 1.0000 Uiso . . . . . . H442 H 0.5421 0.3266 0.0836 0.0417 1.0000 Uiso . . . . . . H471 H 0.7150 0.0927 0.2000 0.0492 1.0000 Uiso . . . . . . H481 H 0.8357 0.0182 0.1495 0.0566 1.0000 Uiso . . . . . . H491 H 0.8812 0.0346 0.0228 0.0547 1.0000 Uiso . . . . . . H501 H 0.8089 0.1259 -0.0591 0.0454 1.0000 Uiso . . . . . . 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 0.0280(8) 0.0202(7) 0.0226(8) 0.0031(6) 0.0024(6) 0.0035(6) C2 0.0240(8) 0.0228(8) 0.0266(8) 0.0031(6) 0.0006(6) 0.0036(6) C3 0.0296(9) 0.0307(9) 0.0347(10) -0.0032(7) 0.0001(7) 0.0008(7) C4 0.0405(10) 0.0363(10) 0.0306(9) -0.0084(8) 0.0031(8) 0.0042(8) C5 0.0354(9) 0.0348(9) 0.0288(9) 0.0026(7) 0.0095(7) 0.0074(7) C6 0.0270(8) 0.0251(8) 0.0240(8) 0.0081(6) 0.0048(6) 0.0041(6) C7 0.0291(8) 0.0273(8) 0.0312(9) 0.0085(7) 0.0093(7) 0.0013(7) C8 0.0183(7) 0.0244(8) 0.0304(9) 0.0002(6) 0.0065(6) -0.0028(6) C9 0.0207(7) 0.0237(8) 0.0310(9) 0.0043(6) 0.0065(6) -0.0032(6) C10 0.0263(8) 0.0289(8) 0.0303(9) 0.0019(7) 0.0081(6) -0.0056(7) C11 0.0226(8) 0.0290(8) 0.0348(9) -0.0015(7) 0.0092(7) -0.0007(7) C12 0.0201(7) 0.0280(8) 0.0348(9) 0.0013(7) 0.0048(6) 0.0003(7) C13 0.0194(7) 0.0258(8) 0.0282(9) 0.0012(6) 0.0037(6) -0.0027(6) C14 0.0209(7) 0.0335(9) 0.0251(8) 0.0033(7) 0.0021(6) 0.0013(7) C15 0.0242(8) 0.0264(8) 0.0209(8) 0.0025(6) 0.0035(6) 0.0030(6) C16 0.0297(8) 0.0305(9) 0.0274(9) 0.0028(7) 0.0082(7) 0.0065(7) C17 0.0437(10) 0.0225(8) 0.0347(9) -0.0008(7) 0.0128(8) 0.0050(7) C18 0.0350(9) 0.0235(8) 0.0332(9) 0.0027(7) 0.0102(7) -0.0023(7) C19 0.0277(8) 0.0252(8) 0.0217(8) 0.0043(6) 0.0067(6) 0.0019(6) C20 0.0263(8) 0.0207(7) 0.0185(7) 0.0020(6) 0.0019(6) 0.0027(6) C21 0.0261(8) 0.0270(8) 0.0268(8) 0.0033(6) 0.0093(6) -0.0008(6) C22 0.0200(7) 0.0216(7) 0.0276(8) -0.0038(6) 0.0076(6) -0.0008(6) C23 0.0240(8) 0.0238(8) 0.0275(8) -0.0013(6) 0.0094(6) -0.0004(6) C24 0.0289(8) 0.0224(8) 0.0355(9) -0.0007(7) 0.0116(7) -0.0029(7) C25 0.0240(8) 0.0293(9) 0.0439(10) -0.0062(8) 0.0079(7) -0.0064(7) C26 0.0216(8) 0.0299(8) 0.0351(9) -0.0046(7) 0.0027(7) -0.0006(7) C27 0.0208(7) 0.0239(8) 0.0293(8) -0.0019(6) 0.0063(6) 0.0013(6) C28 0.0220(8) 0.0254(8) 0.0320(9) 0.0010(7) 0.0035(6) 0.0028(6) O1 0.0274(6) 0.0197(5) 0.0266(6) 0.0015(4) 0.0022(4) 0.0028(4) C29 0.0284(8) 0.0195(7) 0.0311(9) 0.0034(6) 0.0061(7) 0.0027(6) C30 0.0295(8) 0.0263(8) 0.0332(9) 0.0005(7) 0.0104(7) 0.0014(7) O2 0.0308(6) 0.0304(6) 0.0295(6) -0.0051(5) 0.0065(5) -0.0011(5) C31 0.0426(10) 0.0307(9) 0.0307(9) -0.0066(7) -0.0012(8) 0.0044(8) C32 0.0463(11) 0.0284(9) 0.0455(11) -0.0059(8) -0.0032(9) -0.0024(8) N1 0.0349(8) 0.0303(8) 0.0331(8) -0.0024(6) 0.0049(6) -0.0037(6) C33 0.0316(9) 0.0335(9) 0.0300(9) -0.0036(7) 0.0039(7) -0.0044(7) C34 0.0249(8) 0.0327(9) 0.0383(10) -0.0074(7) 0.0038(7) -0.0085(7) C35 0.0304(10) 0.0386(11) 0.0598(13) -0.0051(9) -0.0034(9) -0.0042(8) C36 0.0271(10) 0.0417(12) 0.098(2) -0.0175(12) 0.0031(11) -0.0036(9) C37 0.0342(11) 0.0518(14) 0.108(2) -0.0384(14) 0.0275(13) -0.0143(10) C38 0.0453(12) 0.0553(13) 0.0618(14) -0.0262(11) 0.0284(10) -0.0265(11) C39 0.0332(9) 0.0365(10) 0.0425(11) -0.0110(8) 0.0141(8) -0.0156(8) C40 0.0443(11) 0.0387(10) 0.0346(10) -0.0030(8) 0.0107(8) -0.0198(8) O3 0.0502(8) 0.0557(9) 0.0307(7) -0.0027(6) 0.0096(6) 0.0047(7) O4 0.0744(11) 0.0557(9) 0.0395(8) 0.0113(7) 0.0129(7) -0.0220(8) O5 0.0269(6) 0.0368(7) 0.0288(6) 0.0048(5) 0.0082(5) 0.0103(5) O6 0.0266(5) 0.0223(5) 0.0216(5) -0.0019(4) 0.0039(4) 0.0029(4) C41 0.0280(8) 0.0318(9) 0.0223(8) -0.0013(7) 0.0017(6) 0.0021(7) C42 0.0290(8) 0.0301(9) 0.0311(9) -0.0066(7) 0.0033(7) -0.0012(7) O7 0.0269(6) 0.0223(5) 0.0381(7) 0.0017(5) 0.0085(5) 0.0026(4) C43 0.0324(8) 0.0217(8) 0.0257(8) 0.0015(6) 0.0025(7) -0.0004(6) C44 0.0307(9) 0.0223(8) 0.0512(11) -0.0049(8) 0.0077(8) 0.0027(7) N2 0.0294(7) 0.0252(7) 0.0384(8) -0.0029(6) 0.0055(6) 0.0013(6) C45 0.0270(8) 0.0328(9) 0.0382(10) -0.0046(7) 0.0067(7) -0.0044(7) C46 0.0255(8) 0.0271(8) 0.0378(10) -0.0024(7) 0.0014(7) -0.0039(7) C47 0.0378(10) 0.0397(11) 0.0454(11) 0.0044(9) -0.0034(8) -0.0031(8) C48 0.0391(11) 0.0360(10) 0.0665(15) 0.0026(10) -0.0086(10) 0.0061(9) C49 0.0301(9) 0.0364(10) 0.0701(15) -0.0135(10) -0.0020(9) 0.0075(8) C50 0.0290(9) 0.0361(10) 0.0483(11) -0.0144(8) 0.0032(8) -0.0004(8) C51 0.0222(8) 0.0266(8) 0.0362(9) -0.0065(7) -0.0007(7) -0.0025(6) C52 0.0256(8) 0.0254(8) 0.0354(10) -0.0073(7) 0.0026(7) -0.0035(7) O8 0.0418(8) 0.0519(8) 0.0451(8) -0.0053(7) 0.0186(6) -0.0028(6) O9 0.0436(7) 0.0339(7) 0.0363(7) -0.0008(6) 0.0053(6) -0.0040(6) O10 0.0247(6) 0.0233(6) 0.0310(6) 0.0043(5) -0.0008(5) -0.0064(5) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.396(2) yes C1 . C6 . 1.401(2) yes C1 . O1 . 1.3917(19) yes C2 . C3 . 1.391(2) yes C2 . C28 . 1.518(2) yes C3 . C4 . 1.385(3) yes C3 . H31 . 1.000 no C4 . C5 . 1.384(3) yes C4 . H41 . 1.000 no C5 . C6 . 1.390(2) yes C5 . H51 . 1.000 no C6 . C7 . 1.518(2) yes C7 . C9 . 1.516(2) yes C7 . H71 . 1.000 no C7 . H72 . 1.000 no C8 . C9 . 1.403(2) yes C8 . C13 . 1.398(2) yes C8 . O5 . 1.3641(19) yes C9 . C10 . 1.392(2) yes C10 . C11 . 1.384(2) yes C10 . H101 . 1.000 no C11 . C12 . 1.386(2) yes C11 . H111 . 1.000 no C12 . C13 . 1.391(2) yes C12 . H121 . 1.000 no C13 . C14 . 1.517(2) yes C14 . C15 . 1.519(2) yes C14 . H141 . 1.000 no C14 . H142 . 1.000 no C15 . C16 . 1.394(2) yes C15 . C20 . 1.395(2) yes C16 . C17 . 1.387(2) yes C16 . H161 . 1.000 no C17 . C18 . 1.384(2) yes C17 . H171 . 1.000 no C18 . C19 . 1.394(2) yes C18 . H181 . 1.000 no C19 . C20 . 1.394(2) yes C19 . C21 . 1.520(2) yes C20 . O6 . 1.3951(18) yes C21 . C23 . 1.515(2) yes C21 . H211 . 1.000 no C21 . H212 . 1.000 no C22 . C23 . 1.400(2) yes C22 . C27 . 1.402(2) yes C22 . O10 . 1.3596(18) yes C23 . C24 . 1.392(2) yes C24 . C25 . 1.383(2) yes C24 . H241 . 1.000 no C25 . C26 . 1.388(2) yes C25 . H251 . 1.000 no C26 . C27 . 1.386(2) yes C26 . H261 . 1.000 no C27 . C28 . 1.515(2) yes C28 . H281 . 1.000 no C28 . H282 . 1.000 no O1 . C29 . 1.4458(18) yes C29 . C30 . 1.490(2) yes C29 . H291 . 1.000 no C29 . H292 . 1.000 no C30 . O2 . 1.424(2) yes C30 . H301 . 1.000 no C30 . H302 . 1.000 no O2 . C31 . 1.413(2) yes C31 . C32 . 1.507(3) yes C31 . H311 . 1.000 no C31 . H312 . 1.000 no C32 . N1 . 1.452(2) yes C32 . H321 . 1.000 no C32 . H322 . 1.000 no N1 . C33 . 1.391(2) yes N1 . C40 . 1.397(2) yes C33 . C34 . 1.486(2) yes C33 . O3 . 1.209(2) yes C34 . C35 . 1.378(3) yes C34 . C39 . 1.384(3) yes C35 . C36 . 1.385(3) yes C35 . H351 . 1.000 no C36 . C37 . 1.383(4) yes C36 . H361 . 1.000 no C37 . C38 . 1.390(4) yes C37 . H371 . 1.000 no C38 . C39 . 1.384(3) yes C38 . H381 . 1.000 no C39 . C40 . 1.480(3) yes C40 . O4 . 1.213(2) yes O5 . H1 . 0.87(3) no O6 . C41 . 1.4337(19) yes C41 . C42 . 1.504(2) yes C41 . H411 . 1.000 no C41 . H412 . 1.000 no C42 . O7 . 1.430(2) yes C42 . H421 . 1.000 no C42 . H422 . 1.000 no O7 . C43 . 1.4157(19) yes C43 . C44 . 1.509(2) yes C43 . H431 . 1.000 no C43 . H432 . 1.000 no C44 . N2 . 1.458(2) yes C44 . H441 . 1.000 no C44 . H442 . 1.000 no N2 . C45 . 1.391(2) yes N2 . C52 . 1.399(2) yes C45 . C46 . 1.489(2) yes C45 . O8 . 1.208(2) yes C46 . C47 . 1.382(3) yes C46 . C51 . 1.382(2) yes C47 . C48 . 1.392(3) yes C47 . H471 . 1.000 no C48 . C49 . 1.384(3) yes C48 . H481 . 1.000 no C49 . C50 . 1.393(3) yes C49 . H491 . 1.000 no C50 . C51 . 1.387(2) yes C50 . H501 . 1.000 no C51 . C52 . 1.487(2) yes C52 . O9 . 1.210(2) yes O10 . H2 . 0.92(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . C6 . 122.42(15) yes C2 . C1 . O1 . 119.84(14) yes C6 . C1 . O1 . 117.67(14) yes C1 . C2 . C3 . 117.36(15) yes C1 . C2 . C28 . 122.59(14) yes C3 . C2 . C28 . 120.02(14) yes C2 . C3 . C4 . 121.49(16) yes C2 . C3 . H31 . 119.254 no C4 . C3 . H31 . 119.254 no C3 . C4 . C5 . 119.72(16) yes C3 . C4 . H41 . 120.139 no C5 . C4 . H41 . 120.139 no C4 . C5 . C6 . 121.05(16) yes C4 . C5 . H51 . 119.476 no C6 . C5 . H51 . 119.476 no C1 . C6 . C5 . 117.80(15) yes C1 . C6 . C7 . 121.71(14) yes C5 . C6 . C7 . 120.41(14) yes C6 . C7 . C9 . 110.64(13) yes C6 . C7 . H71 . 109.181 no C9 . C7 . H71 . 109.181 no C6 . C7 . H72 . 109.181 no C9 . C7 . H72 . 109.181 no H71 . C7 . H72 . 109.467 no C9 . C8 . C13 . 121.07(14) yes C9 . C8 . O5 . 122.25(14) yes C13 . C8 . O5 . 116.67(14) yes C7 . C9 . C8 . 121.05(14) yes C7 . C9 . C10 . 120.44(14) yes C8 . C9 . C10 . 118.46(15) yes C9 . C10 . C11 . 121.18(15) yes C9 . C10 . H101 . 119.410 no C11 . C10 . H101 . 119.410 no C10 . C11 . C12 . 119.52(15) yes C10 . C11 . H111 . 120.240 no C12 . C11 . H111 . 120.240 no C11 . C12 . C13 . 121.15(15) yes C11 . C12 . H121 . 119.427 no C13 . C12 . H121 . 119.427 no C8 . C13 . C12 . 118.59(15) yes C8 . C13 . C14 . 120.12(14) yes C12 . C13 . C14 . 121.28(14) yes C13 . C14 . C15 . 111.66(13) yes C13 . C14 . H141 . 108.923 no C15 . C14 . H141 . 108.923 no C13 . C14 . H142 . 108.923 no C15 . C14 . H142 . 108.923 no H141 . C14 . H142 . 109.467 no C14 . C15 . C16 . 120.27(14) yes C14 . C15 . C20 . 122.02(14) yes C16 . C15 . C20 . 117.58(15) yes C15 . C16 . C17 . 121.05(15) yes C15 . C16 . H161 . 119.474 no C17 . C16 . H161 . 119.475 no C16 . C17 . C18 . 120.06(15) yes C16 . C17 . H171 . 119.969 no C18 . C17 . H171 . 119.969 no C17 . C18 . C19 . 120.75(15) yes C17 . C18 . H181 . 119.623 no C19 . C18 . H181 . 119.623 no C18 . C19 . C20 . 117.93(14) yes C18 . C19 . C21 . 120.39(14) yes C20 . C19 . C21 . 121.61(14) yes C15 . C20 . C19 . 122.55(14) yes C15 . C20 . O6 . 119.13(14) yes C19 . C20 . O6 . 118.02(13) yes C19 . C21 . C23 . 112.44(13) yes C19 . C21 . H211 . 108.724 no C23 . C21 . H211 . 108.724 no C19 . C21 . H212 . 108.724 no C23 . C21 . H212 . 108.724 no H211 . C21 . H212 . 109.467 no C23 . C22 . C27 . 121.30(14) yes C23 . C22 . O10 . 123.34(14) yes C27 . C22 . O10 . 115.36(14) yes C21 . C23 . C22 . 121.45(14) yes C21 . C23 . C24 . 120.58(14) yes C22 . C23 . C24 . 117.97(15) yes C23 . C24 . C25 . 121.77(15) yes C23 . C24 . H241 . 119.115 no C25 . C24 . H241 . 119.115 no C24 . C25 . C26 . 119.09(15) yes C24 . C25 . H251 . 120.457 no C26 . C25 . H251 . 120.457 no C25 . C26 . C27 . 121.33(15) yes C25 . C26 . H261 . 119.336 no C27 . C26 . H261 . 119.336 no C22 . C27 . C26 . 118.52(15) yes C22 . C27 . C28 . 119.33(14) yes C26 . C27 . C28 . 122.14(14) yes C2 . C28 . C27 . 112.61(13) yes C2 . C28 . H281 . 108.683 no C27 . C28 . H281 . 108.683 no C2 . C28 . H282 . 108.683 no C27 . C28 . H282 . 108.683 no H281 . C28 . H282 . 109.467 no C1 . O1 . C29 . 114.02(11) yes O1 . C29 . C30 . 107.24(13) yes O1 . C29 . H291 . 110.027 no C30 . C29 . H291 . 110.026 no O1 . C29 . H292 . 110.027 no C30 . C29 . H292 . 110.027 no H291 . C29 . H292 . 109.467 no C29 . C30 . O2 . 108.19(13) yes C29 . C30 . H301 . 109.791 no O2 . C30 . H301 . 109.791 no C29 . C30 . H302 . 109.791 no O2 . C30 . H302 . 109.791 no H301 . C30 . H302 . 109.467 no C30 . O2 . C31 . 111.12(13) yes O2 . C31 . C32 . 108.08(15) yes O2 . C31 . H311 . 109.818 no C32 . C31 . H311 . 109.818 no O2 . C31 . H312 . 109.818 no C32 . C31 . H312 . 109.818 no H311 . C31 . H312 . 109.467 no C31 . C32 . N1 . 112.49(15) yes C31 . C32 . H321 . 108.711 no N1 . C32 . H321 . 108.711 no C31 . C32 . H322 . 108.711 no N1 . C32 . H322 . 108.711 no H321 . C32 . H322 . 109.467 no C32 . N1 . C33 . 123.56(15) yes C32 . N1 . C40 . 124.51(16) yes C33 . N1 . C40 . 111.88(15) yes N1 . C33 . C34 . 105.90(15) yes N1 . C33 . O3 . 124.36(17) yes C34 . C33 . O3 . 129.74(17) yes C33 . C34 . C35 . 129.83(17) yes C33 . C34 . C39 . 108.01(16) yes C35 . C34 . C39 . 122.12(18) yes C34 . C35 . C36 . 117.0(2) yes C34 . C35 . H351 . 121.487 no C36 . C35 . H351 . 121.487 no C35 . C36 . C37 . 121.4(2) yes C35 . C36 . H361 . 119.320 no C37 . C36 . H361 . 119.320 no C36 . C37 . C38 . 121.3(2) yes C36 . C37 . H371 . 119.335 no C38 . C37 . H371 . 119.335 no C37 . C38 . C39 . 117.3(2) yes C37 . C38 . H381 . 121.366 no C39 . C38 . H381 . 121.366 no C38 . C39 . C34 . 120.9(2) yes C38 . C39 . C40 . 130.71(19) yes C34 . C39 . C40 . 108.37(16) yes C39 . C40 . N1 . 105.78(15) yes C39 . C40 . O4 . 129.78(19) yes N1 . C40 . O4 . 124.4(2) yes C8 . O5 . H1 . 111.8(16) no C20 . O6 . C41 . 117.20(11) yes O6 . C41 . C42 . 106.05(13) yes O6 . C41 . H411 . 110.321 no C42 . C41 . H411 . 110.321 no O6 . C41 . H412 . 110.321 no C42 . C41 . H412 . 110.321 no H411 . C41 . H412 . 109.467 no C41 . C42 . O7 . 107.89(13) yes C41 . C42 . H421 . 109.865 no O7 . C42 . H421 . 109.865 no C41 . C42 . H422 . 109.865 no O7 . C42 . H422 . 109.865 no H421 . C42 . H422 . 109.467 no C42 . O7 . C43 . 114.40(12) yes O7 . C43 . C44 . 107.03(13) yes O7 . C43 . H431 . 110.078 no C44 . C43 . H431 . 110.079 no O7 . C43 . H432 . 110.078 no C44 . C43 . H432 . 110.079 no H431 . C43 . H432 . 109.467 no C43 . C44 . N2 . 112.24(13) yes C43 . C44 . H441 . 108.776 no N2 . C44 . H441 . 108.775 no C43 . C44 . H442 . 108.775 no N2 . C44 . H442 . 108.775 no H441 . C44 . H442 . 109.467 no C44 . N2 . C45 . 124.53(15) yes C44 . N2 . C52 . 123.32(15) yes C45 . N2 . C52 . 111.93(14) yes N2 . C45 . C46 . 105.91(14) yes N2 . C45 . O8 . 124.89(17) yes C46 . C45 . O8 . 129.19(17) yes C45 . C46 . C47 . 130.20(17) yes C45 . C46 . C51 . 108.03(15) yes C47 . C46 . C51 . 121.76(17) yes C46 . C47 . C48 . 117.27(19) yes C46 . C47 . H471 . 121.365 no C48 . C47 . H471 . 121.365 no C47 . C48 . C49 . 120.93(19) yes C47 . C48 . H481 . 119.534 no C49 . C48 . H481 . 119.534 no C48 . C49 . C50 . 121.80(18) yes C48 . C49 . H491 . 119.101 no C50 . C49 . H491 . 119.101 no C49 . C50 . C51 . 116.78(18) yes C49 . C50 . H501 . 121.611 no C51 . C50 . H501 . 121.611 no C50 . C51 . C46 . 121.46(17) yes C50 . C51 . C52 . 130.16(17) yes C46 . C51 . C52 . 108.38(15) yes C51 . C52 . N2 . 105.62(15) yes C51 . C52 . O9 . 129.50(16) yes N2 . C52 . O9 . 124.88(16) yes C22 . O10 . H2 . 113.4(15) no 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_publ_flag O5 H1 O1 0.87(3) 1.95(3) 2.8004(16) 166(2) yes O10 H2 O6 0.92(3) 1.81(3) 2.7028(16) 163(2) yes loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag O1 O10 2.8901(15) yes O6 O5 2.9227(16) yes #===END #============================================================================== data_17 _database_code_depnum_ccdc_archive 'CCDC 839216' #TrackingRef '- crystallographicdata.cif' #============================================================================== _audit_creation_date 07-03-16 _audit_creation_method CRYSTALS_ver_12.84 # start Validation Reply Form _vrf_PLAT432_CRYSTALS_cif ; PROBLEM: Short Inter X...Y Contact O200 .. C202 .. 2.22 Ang. RESPONSE: The title compound was recrystallised from a mixture of ethyl acetate and acetone. Attempts to model the solvent disordered across the centre of symmetry with either or a mixture of these solvents was unsuccessful, even with distance and adp restraints. The current atoms are simply place-holders. SQUEEZE may be a more satisfactory alternative. ; # end Validation Reply Form _oxford_structure_analysis_title '3140748 Compound 84' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 13.37900(10) _cell_length_b 15.0967(2) _cell_length_c 20.7767(3) _cell_angle_alpha 90 _cell_angle_beta 103.7671(5) _cell_angle_gamma 90 _cell_volume 4075.89(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/a 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z x+1/2,-y+1/2,z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C40 H25 N1 O12 # Dc = 1.16 Fooo = 1784.00 Mu = 0.87 M = 711.64 # Found Formula = C46.50 H50 N3 O12 # Dc = 1.37 FOOO = 1784.00 Mu = 1.00 M = 842.92 _chemical_formula_sum 'C46.50 H50 N3 O12' _chemical_formula_moiety 'C44 H43 N3 O10, H20, .5(C5 H10 O2)' _chemical_compound_source ? _chemical_formula_weight 842.92 _cell_measurement_reflns_used 10907 _cell_measurement_theta_min 5 _cell_measurement_theta_max 29 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_max 0.44 _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1784 _exptl_absorpt_coefficient_mu 0.100 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material CRYSTALS _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 87793 _reflns_number_total 10734 _diffrn_reflns_av_R_equivalents 0.069 # Number of reflections with Friedels Law is 10734 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 10857 _diffrn_reflns_theta_min 5.125 _diffrn_reflns_theta_max 29.070 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.198 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -18 _reflns_limit_h_max 17 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 2.33 _oxford_diffrn_Wilson_scale 14.43 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.58 _refine_diff_density_max 0.39 _refine_ls_number_reflns 6235 _refine_ls_number_restraints 3 _refine_ls_number_parameters 559 #_refine_ls_R_factor_ref 0.0519 _refine_ls_wR_factor_ref 0.0595 _refine_ls_goodness_of_fit_ref 1.0808 #_reflns_number_all 10734 _refine_ls_R_factor_all 0.1113 _refine_ls_wR_factor_all 0.0847 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6235 _refine_ls_R_factor_gt 0.0519 _refine_ls_wR_factor_gt 0.0595 _refine_ls_shift/su_max 0.000230 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.01P)^2^ + 0.04P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fig. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. These were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H to 0.86, O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. The material was recrystallised from a mixture of ethyl acetate and acetone. Attempts to model the solvent disordered across the centre of symmetry with either or a mixture of these solvents was unsuccessful, even with distance and adp restraints. The current atoms are simply place-holders. SQUEEZE may be a more satisfactory alternative. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; Mixture of acetone and ethyl acetate allowed to evaporate freely until crystals formed. ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens N1 N -0.31048(16) 0.42536(13) 0.32119(10) 0.0416 1.0000 Uani . . . . . . . C2 C -0.21253(17) 0.46965(15) 0.35143(11) 0.0340 1.0000 Uani . . . . . . . C3 C -0.20387(18) 0.55929(15) 0.34072(11) 0.0347 1.0000 Uani . . . . . . . C4 C -0.10926(18) 0.59948(14) 0.36621(11) 0.0341 1.0000 Uani . . . . . . . C5 C -0.02665(17) 0.54981(14) 0.40099(11) 0.0331 1.0000 Uani . . . . . . . C6 C -0.03729(17) 0.45925(14) 0.41167(10) 0.0317 1.0000 Uani . . . . . . . C7 C -0.13211(18) 0.41954(14) 0.38720(10) 0.0339 1.0000 Uani . . . . . . . C8 C 0.04814(18) 0.40091(15) 0.44919(10) 0.0343 1.0000 Uani . . . . . . . N9 N 0.14461(15) 0.43277(12) 0.45961(9) 0.0377 1.0000 Uani . . . . . . . C10 C 0.23286(19) 0.38101(17) 0.49484(11) 0.0418 1.0000 Uani . . . . . . . C11 C 0.28164(18) 0.32746(16) 0.44982(11) 0.0378 1.0000 Uani . . . . . . . O12 O 0.31935(11) 0.38673(10) 0.40779(7) 0.0355 1.0000 Uani . . . . . . . C13 C 0.36744(17) 0.34045(15) 0.36408(11) 0.0359 1.0000 Uani . . . . . . . C14 C 0.39837(16) 0.40330(16) 0.31656(11) 0.0374 1.0000 Uani . . . . . . . O15 O 0.31253(10) 0.43826(10) 0.26662(7) 0.0314 1.0000 Uani . . . . . . . C16 C 0.25920(16) 0.37357(13) 0.22344(10) 0.0296 1.0000 Uani . . . . . . . C17 C 0.16422(16) 0.34415(14) 0.23165(10) 0.0296 1.0000 Uani . . . . . . . C18 C 0.11176(16) 0.38341(15) 0.28240(10) 0.0320 1.0000 Uani . . . . . . . C19 C 0.01320(15) 0.42953(14) 0.24693(10) 0.0276 1.0000 Uani . . . . . . . C20 C 0.01692(15) 0.51309(14) 0.21846(10) 0.0263 1.0000 Uani . . . . . . . C21 C -0.07151(15) 0.55381(14) 0.18069(10) 0.0279 1.0000 Uani . . . . . . . C22 C -0.06773(17) 0.64396(15) 0.14875(12) 0.0347 1.0000 Uani . . . . . . . C23 C -0.02212(16) 0.64130(14) 0.08845(11) 0.0324 1.0000 Uani . . . . . . . C24 C 0.08013(16) 0.66538(13) 0.09306(10) 0.0289 1.0000 Uani . . . . . . . C25 C 0.12700(16) 0.65504(14) 0.04041(11) 0.0307 1.0000 Uani . . . . . . . C26 C 0.24220(16) 0.66928(14) 0.04879(11) 0.0320 1.0000 Uani . . . . . . . C27 C 0.29755(15) 0.58312(14) 0.04413(10) 0.0297 1.0000 Uani . . . . . . . C28 C 0.32201(15) 0.52644(15) 0.09925(10) 0.0292 1.0000 Uani . . . . . . . C29 C 0.37042(16) 0.44492(15) 0.09621(11) 0.0341 1.0000 Uani . . . . . . . C30 C 0.39558(18) 0.38420(17) 0.15577(13) 0.0442 1.0000 Uani . . . . . . . C31 C 0.29959(17) 0.34397(15) 0.17102(11) 0.0356 1.0000 Uani . . . . . . . C32 C 0.2447(2) 0.27923(16) 0.12930(12) 0.0447 1.0000 Uani . . . . . . . C33 C 0.1530(2) 0.24660(16) 0.13842(13) 0.0463 1.0000 Uani . . . . . . . C34 C 0.11327(18) 0.27976(15) 0.18848(12) 0.0396 1.0000 Uani . . . . . . . C35 C 0.39420(16) 0.42127(16) 0.03694(12) 0.0375 1.0000 Uani . . . . . . . C36 C 0.37205(17) 0.47636(17) -0.01757(11) 0.0383 1.0000 Uani . . . . . . . C37 C 0.32393(16) 0.55625(16) -0.01360(11) 0.0343 1.0000 Uani . . . . . . . O38 O 0.29661(12) 0.55669(10) 0.15524(7) 0.0358 1.0000 Uani . . . . . . . C39 C 0.06627(18) 0.62527(15) -0.01968(11) 0.0375 1.0000 Uani . . . . . . . C40 C -0.03596(18) 0.60374(16) -0.02624(12) 0.0412 1.0000 Uani . . . . . . . C41 C -0.07950(17) 0.61100(15) 0.02718(12) 0.0383 1.0000 Uani . . . . . . . O42 O 0.13862(11) 0.69387(9) 0.15472(7) 0.0297 1.0000 Uani . . . . . . . C43 C 0.15682(18) 0.78812(14) 0.16136(12) 0.0350 1.0000 Uani . . . . . . . C44 C 0.07155(18) 0.83772(14) 0.18105(11) 0.0353 1.0000 Uani . . . . . . . O45 O 0.06957(11) 0.80985(9) 0.24598(7) 0.0340 1.0000 Uani . . . . . . . C46 C -0.01240(18) 0.84814(15) 0.26917(12) 0.0373 1.0000 Uani . . . . . . . C47 C 0.0026(2) 0.82452(15) 0.34082(13) 0.0436 1.0000 Uani . . . . . . . N48 N -0.01201(15) 0.73021(12) 0.35151(10) 0.0404 1.0000 Uani . . . . . . . C49 C -0.10277(19) 0.69810(15) 0.35588(12) 0.0388 1.0000 Uani . . . . . . . O50 O -0.17968(14) 0.74416(11) 0.35187(11) 0.0568 1.0000 Uani . . . . . . . C51 C -0.16458(16) 0.50916(15) 0.17299(11) 0.0316 1.0000 Uani . . . . . . . C52 C -0.17047(16) 0.42728(15) 0.20107(11) 0.0342 1.0000 Uani . . . . . . . C53 C -0.08198(17) 0.38759(14) 0.23731(10) 0.0314 1.0000 Uani . . . . . . . O54 O 0.11294(10) 0.55177(9) 0.23100(7) 0.0315 1.0000 Uani . . . . . . . O55 O 0.02824(13) 0.32816(11) 0.46946(8) 0.0471 1.0000 Uani . . . . . . . O56 O -0.37722(13) 0.46747(13) 0.28305(11) 0.0574 1.0000 Uani . . . . . . . O57 O -0.32087(17) 0.34810(13) 0.33300(12) 0.0800 1.0000 Uani . . . . . . . O100 O 0.17790(13) 0.62045(11) 0.36262(8) 0.0449 1.0000 Uani . . . . . . . C200 C 0.52984(19) 0.4878(2) 0.48357(11) 0.0730 0.5000 Uani D . . 1 1 . . O200 O 0.52980(19) 0.4883(2) 0.48383(11) 0.0730 0.5000 Uani . . . 1 2 . . O201 O 0.5611(2) 0.5027(2) 0.43161(15) 0.0399 0.5000 Uani D . . . . . . C202 C 0.5844(3) 0.4067(3) 0.51511(15) 0.0849 1.0000 Uani D . . . . . . C203 C 0.6437(4) 0.3849(4) 0.4736(3) 0.1346 1.0000 Uani D . . . . . . H31 H -0.2599 0.5924 0.3170 0.0437 1.0000 Uiso R . . . . . . H51 H 0.0372 0.5785 0.4182 0.0412 1.0000 Uiso R . . . . . . H71 H -0.1406 0.3591 0.3939 0.0421 1.0000 Uiso R . . . . . . H101 H 0.2829 0.4238 0.5191 0.0478 1.0000 Uiso R . . . . . . H102 H 0.2099 0.3398 0.5251 0.0475 1.0000 Uiso R . . . . . . H111 H 0.3384 0.2912 0.4758 0.0431 1.0000 Uiso R . . . . . . H112 H 0.2304 0.2870 0.4222 0.0440 1.0000 Uiso R . . . . . . H131 H 0.4304 0.3123 0.3903 0.0412 1.0000 Uiso R . . . . . . H132 H 0.3201 0.2943 0.3408 0.0404 1.0000 Uiso R . . . . . . H141 H 0.4328 0.4534 0.3407 0.0426 1.0000 Uiso R . . . . . . H142 H 0.4452 0.3730 0.2940 0.0432 1.0000 Uiso R . . . . . . H181 H 0.1567 0.4258 0.3117 0.0378 1.0000 Uiso R . . . . . . H182 H 0.0948 0.3356 0.3094 0.0376 1.0000 Uiso R . . . . . . H221 H -0.0289 0.6837 0.1821 0.0408 1.0000 Uiso R . . . . . . H222 H -0.1387 0.6637 0.1340 0.0421 1.0000 Uiso R . . . . . . H261 H 0.2534 0.7093 0.0147 0.0379 1.0000 Uiso R . . . . . . H262 H 0.2700 0.6963 0.0925 0.0381 1.0000 Uiso R . . . . . . H301 H 0.4353 0.4169 0.1939 0.0529 1.0000 Uiso R . . . . . . H302 H 0.4379 0.3365 0.1449 0.0538 1.0000 Uiso R . . . . . . H321 H 0.2724 0.2593 0.0948 0.0528 1.0000 Uiso R . . . . . . H331 H 0.1168 0.2024 0.1100 0.0527 1.0000 Uiso R . . . . . . H341 H 0.0486 0.2584 0.1940 0.0465 1.0000 Uiso R . . . . . . H351 H 0.4269 0.3660 0.0349 0.0450 1.0000 Uiso R . . . . . . H361 H 0.3903 0.4603 -0.0571 0.0474 1.0000 Uiso R . . . . . . H371 H 0.3066 0.5928 -0.0506 0.0411 1.0000 Uiso R . . . . . . H391 H 0.0961 0.6190 -0.0564 0.0448 1.0000 Uiso R . . . . . . H401 H -0.0753 0.5826 -0.0680 0.0466 1.0000 Uiso R . . . . . . H411 H -0.1475 0.5939 0.0238 0.0452 1.0000 Uiso R . . . . . . H431 H 0.2203 0.7965 0.1966 0.0435 1.0000 Uiso R . . . . . . H432 H 0.1673 0.8112 0.1194 0.0436 1.0000 Uiso R . . . . . . H441 H 0.0861 0.9026 0.1809 0.0426 1.0000 Uiso R . . . . . . H442 H 0.0049 0.8246 0.1503 0.0423 1.0000 Uiso R . . . . . . H461 H -0.0096 0.9118 0.2647 0.0463 1.0000 Uiso R . . . . . . H462 H -0.0806 0.8270 0.2435 0.0467 1.0000 Uiso R . . . . . . H471 H -0.0453 0.8576 0.3588 0.0557 1.0000 Uiso R . . . . . . H472 H 0.0731 0.8409 0.3642 0.0557 1.0000 Uiso R . . . . . . H511 H -0.2244 0.5371 0.1478 0.0372 1.0000 Uiso R . . . . . . H521 H -0.2343 0.3988 0.1955 0.0422 1.0000 Uiso R . . . . . . H531 H -0.0846 0.3316 0.2561 0.0380 1.0000 Uiso R . . . . . . H3 H 0.0401 0.6948 0.3541 0.0511 1.0000 Uiso . . . . . . . H6 H 0.1152 0.5962 0.2074 0.0474 1.0000 Uiso . . . . . . . H7 H 0.1521 0.4839 0.4425 0.0466 1.0000 Uiso . . . . . . . H9 H 0.3072 0.5225 0.1865 0.0555 1.0000 Uiso . . . . . . . H11 H 0.1677 0.5962 0.3246 0.0692 1.0000 Uiso . . . . . . . H12 H 0.2186 0.6599 0.3584 0.0693 1.0000 Uiso . . . . . . . H2021 H 0.6267 0.4209 0.5591 0.1017 1.0000 Uiso . . . . . . . H2022 H 0.5373 0.3580 0.5184 0.1017 1.0000 Uiso . . . . . . . H2031 H 0.6819 0.3272 0.4908 0.2007 1.0000 Uiso . . . . . . . H2032 H 0.6977 0.4355 0.4740 0.2006 1.0000 Uiso . . . . . . . H2033 H 0.5960 0.3742 0.4270 0.2007 1.0000 Uiso . . . . . . . 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 N1 0.0442(12) 0.0326(11) 0.0476(12) -0.0051(9) 0.0100(10) -0.0029(9) C2 0.0411(13) 0.0305(12) 0.0336(12) -0.0062(10) 0.0153(10) -0.0059(10) C3 0.0408(13) 0.0322(12) 0.0367(12) -0.0018(10) 0.0206(10) 0.0010(10) C4 0.0436(13) 0.0272(11) 0.0387(12) -0.0036(10) 0.0242(11) -0.0040(10) C5 0.0399(12) 0.0305(12) 0.0342(12) -0.0033(9) 0.0189(10) -0.0066(10) C6 0.0442(13) 0.0309(12) 0.0235(11) -0.0041(9) 0.0151(10) -0.0046(10) C7 0.0493(14) 0.0238(11) 0.0309(11) -0.0028(9) 0.0143(10) -0.0068(10) C8 0.0462(14) 0.0312(12) 0.0258(11) -0.0052(9) 0.0094(10) -0.0077(10) N9 0.0483(12) 0.0318(10) 0.0340(10) 0.0009(8) 0.0118(9) -0.0064(9) C10 0.0463(14) 0.0453(14) 0.0298(12) 0.0044(11) 0.0014(11) -0.0094(11) C11 0.0383(12) 0.0375(13) 0.0334(12) 0.0097(10) 0.0001(10) -0.0042(10) O12 0.0381(8) 0.0324(8) 0.0333(8) 0.0067(7) 0.0031(7) -0.0050(7) C13 0.0307(11) 0.0369(13) 0.0354(12) 0.0081(10) -0.0016(10) 0.0025(10) C14 0.0257(11) 0.0431(13) 0.0383(13) 0.0089(11) -0.0026(10) -0.0025(10) O15 0.0275(7) 0.0315(8) 0.0321(8) 0.0058(6) 0.0007(6) -0.0008(6) C16 0.0300(11) 0.0241(11) 0.0309(11) 0.0057(9) -0.0002(9) 0.0056(9) C17 0.0318(11) 0.0246(11) 0.0294(11) 0.0050(9) 0.0009(9) 0.0020(9) C18 0.0365(12) 0.0315(12) 0.0264(11) 0.0051(9) 0.0044(9) -0.0066(9) C19 0.0299(11) 0.0313(11) 0.0227(10) -0.0034(9) 0.0083(8) -0.0046(9) C20 0.0258(10) 0.0296(11) 0.0255(10) -0.0057(9) 0.0097(8) -0.0058(9) C21 0.0277(11) 0.0295(11) 0.0287(11) -0.0047(9) 0.0113(9) 0.0006(9) C22 0.0268(11) 0.0338(12) 0.0455(13) 0.0020(10) 0.0124(10) 0.0066(9) C23 0.0301(11) 0.0261(11) 0.0410(13) 0.0077(10) 0.0084(10) 0.0079(9) C24 0.0312(11) 0.0220(10) 0.0326(12) 0.0073(9) 0.0057(9) 0.0051(9) C25 0.0351(11) 0.0233(11) 0.0342(12) 0.0079(9) 0.0091(10) 0.0033(9) C26 0.0385(12) 0.0293(11) 0.0313(11) 0.0056(9) 0.0140(10) -0.0043(10) C27 0.0249(10) 0.0344(12) 0.0310(11) -0.0010(9) 0.0088(9) -0.0070(9) C28 0.0217(10) 0.0387(12) 0.0280(11) -0.0018(9) 0.0072(8) -0.0027(9) C29 0.0231(10) 0.0428(13) 0.0368(12) 0.0033(10) 0.0082(9) 0.0055(10) C30 0.0353(13) 0.0522(15) 0.0467(14) 0.0093(12) 0.0134(11) 0.0192(11) C31 0.0351(12) 0.0348(13) 0.0362(12) 0.0098(10) 0.0072(10) 0.0143(10) C32 0.0552(16) 0.0382(14) 0.0394(13) -0.0040(11) 0.0088(12) 0.0212(12) C33 0.0457(15) 0.0327(13) 0.0551(16) -0.0101(12) 0.0013(12) 0.0044(11) C34 0.0374(12) 0.0292(12) 0.0489(14) -0.0032(11) 0.0036(11) -0.0006(10) C35 0.0262(11) 0.0454(14) 0.0432(13) -0.0036(11) 0.0125(10) 0.0054(10) C36 0.0303(11) 0.0548(15) 0.0338(12) -0.0094(11) 0.0155(10) -0.0042(11) C37 0.0305(11) 0.0456(14) 0.0291(11) 0.0022(10) 0.0114(9) -0.0084(10) O38 0.0448(9) 0.0381(9) 0.0266(8) 0.0030(7) 0.0128(7) 0.0070(7) C39 0.0429(13) 0.0375(13) 0.0317(12) 0.0071(10) 0.0079(10) 0.0064(11) C40 0.0384(13) 0.0432(14) 0.0365(13) 0.0070(11) -0.0018(10) 0.0059(11) C41 0.0272(11) 0.0383(13) 0.0464(14) 0.0077(11) 0.0031(10) 0.0063(10) O42 0.0356(8) 0.0216(7) 0.0340(8) 0.0019(6) 0.0126(7) -0.0005(6) C43 0.0426(13) 0.0249(11) 0.0415(13) 0.0012(10) 0.0179(11) -0.0047(10) C44 0.0460(13) 0.0227(11) 0.0401(13) 0.0035(10) 0.0158(11) 0.0001(10) O45 0.0375(8) 0.0290(8) 0.0403(9) 0.0041(7) 0.0185(7) 0.0039(7) C46 0.0402(13) 0.0223(11) 0.0554(15) 0.0011(10) 0.0230(11) 0.0007(10) C47 0.0580(15) 0.0271(12) 0.0556(15) -0.0048(11) 0.0329(13) -0.0072(11) N48 0.0475(12) 0.0268(10) 0.0558(13) 0.0023(9) 0.0297(10) -0.0021(9) C49 0.0471(14) 0.0278(12) 0.0477(14) 0.0009(10) 0.0233(11) -0.0020(11) O50 0.0484(11) 0.0295(9) 0.0975(15) 0.0015(9) 0.0275(10) 0.0034(8) C51 0.0227(10) 0.0394(13) 0.0334(12) -0.0080(10) 0.0080(9) 0.0000(9) C52 0.0270(11) 0.0402(13) 0.0379(12) -0.0108(10) 0.0130(10) -0.0112(10) C53 0.0366(12) 0.0305(11) 0.0310(11) -0.0027(9) 0.0154(10) -0.0087(10) O54 0.0257(7) 0.0293(8) 0.0384(8) 0.0045(6) 0.0055(6) -0.0062(6) O55 0.0562(11) 0.0342(9) 0.0458(10) 0.0086(8) 0.0021(8) -0.0109(8) O56 0.0360(10) 0.0475(11) 0.0869(14) 0.0104(10) 0.0112(10) 0.0022(9) O57 0.0748(14) 0.0313(11) 0.1093(18) 0.0109(11) -0.0273(13) -0.0190(10) O100 0.0451(9) 0.0504(11) 0.0424(9) -0.0056(8) 0.0165(8) -0.0127(8) C200 0.0714(19) 0.105(2) 0.0316(14) 0.0186(14) -0.0097(10) -0.0532(17) O200 0.0714(19) 0.105(2) 0.0316(14) 0.0186(14) -0.0097(10) -0.0532(17) O201 0.0385(18) 0.0456(19) 0.0347(18) -0.0023(15) 0.0071(14) -0.0048(15) C202 0.077(2) 0.136(4) 0.0414(17) 0.006(2) 0.0135(17) -0.042(2) C203 0.130(4) 0.110(4) 0.156(5) -0.022(4) 0.019(4) -0.001(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.2766(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 . C2 . 1.472(3) no N1 . O56 . 1.222(3) no N1 . O57 . 1.207(3) no C2 . C3 . 1.381(3) no C2 . C7 . 1.379(3) no C3 . C4 . 1.390(3) no C3 . H31 . 0.937 no C4 . C5 . 1.388(3) no C4 . C49 . 1.510(3) no C5 . C6 . 1.398(3) no C5 . H51 . 0.949 no C6 . C7 . 1.386(3) no C6 . C8 . 1.505(3) no C7 . H71 . 0.934 no C8 . N9 . 1.346(3) no C8 . O55 . 1.228(3) no N9 . C10 . 1.459(3) no N9 . H7 . 0.866 no C10 . C11 . 1.498(3) no C10 . H101 . 0.979 no C10 . H102 . 0.984 no C11 . O12 . 1.424(3) no C11 . H111 . 0.987 no C11 . H112 . 0.992 no O12 . C13 . 1.416(3) no C13 . C14 . 1.497(3) no C13 . H131 . 0.985 no C13 . H132 . 0.988 no C14 . O15 . 1.451(2) no C14 . H141 . 0.962 no C14 . H142 . 0.980 no O15 . C16 . 1.401(3) no C16 . C17 . 1.394(3) no C16 . C31 . 1.399(3) no C17 . C18 . 1.519(3) no C17 . C34 . 1.387(3) no C18 . C19 . 1.518(3) no C18 . H181 . 0.983 no C18 . H182 . 0.974 no C19 . C20 . 1.399(3) no C19 . C53 . 1.393(3) no C20 . C21 . 1.397(3) no C20 . O54 . 1.378(2) no C21 . C22 . 1.520(3) no C21 . C51 . 1.391(3) no C22 . C23 . 1.519(3) no C22 . H221 . 0.969 no C22 . H222 . 0.973 no C23 . C24 . 1.396(3) no C23 . C41 . 1.398(3) no C24 . C25 . 1.393(3) no C24 . O42 . 1.400(3) no C25 . C26 . 1.524(3) no C25 . C39 . 1.392(3) no C26 . C27 . 1.511(3) no C26 . H261 . 0.969 no C26 . H262 . 0.984 no C27 . C28 . 1.404(3) no C27 . C37 . 1.389(3) no C28 . C29 . 1.399(3) no C28 . O38 . 1.366(2) no C29 . C30 . 1.512(3) no C29 . C35 . 1.390(3) no C30 . C31 . 1.521(3) no C30 . H301 . 0.976 no C30 . H302 . 0.975 no C31 . C32 . 1.394(3) no C32 . C33 . 1.376(4) no C32 . H321 . 0.932 no C33 . C34 . 1.370(3) no C33 . H331 . 0.944 no C34 . H341 . 0.955 no C35 . C36 . 1.379(3) no C35 . H351 . 0.948 no C36 . C37 . 1.379(3) no C36 . H361 . 0.942 no C37 . H371 . 0.929 no O38 . H9 . 0.814 no C39 . C40 . 1.381(3) no C39 . H391 . 0.947 no C40 . C41 . 1.375(3) no C40 . H401 . 0.956 no C41 . H411 . 0.933 no O42 . C43 . 1.445(2) no C43 . C44 . 1.500(3) no C43 . H431 . 0.988 no C43 . H432 . 0.979 no C44 . O45 . 1.419(3) no C44 . H441 . 0.998 no C44 . H442 . 0.986 no O45 . C46 . 1.422(3) no C46 . C47 . 1.497(4) no C46 . H461 . 0.968 no C46 . H462 . 0.994 no C47 . N48 . 1.461(3) no C47 . H471 . 0.955 no C47 . H472 . 0.984 no N48 . C49 . 1.330(3) no N48 . H3 . 0.871 no C49 . O50 . 1.228(3) no C51 . C52 . 1.377(3) no C51 . H511 . 0.945 no C52 . C53 . 1.380(3) no C52 . H521 . 0.938 no C53 . H531 . 0.935 no O54 . H6 . 0.836 no O100 . H11 . 0.852 no O100 . H12 . 0.827 no C200 . C200 2_666 1.224(6) no C200 . O201 . 1.267(3) no C200 . C202 . 1.496(5) no O200 . O200 2_666 1.211(6) no O200 . O201 . 1.271(3) no O200 . C202 . 1.500(5) no C202 . C203 . 1.344(6) no C202 . H2021 . 0.977 no C202 . H2022 . 0.982 no C202 . C203 . 1.344(6) no C202 . H2021 . 0.977 no C202 . H2022 . 0.982 no C203 . H2031 . 1.030 no C203 . H2032 . 1.050 no C203 . H2033 . 1.037 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . O56 . 118.65(19) no C2 . N1 . O57 . 119.1(2) no O56 . N1 . O57 . 122.2(2) no N1 . C2 . C3 . 118.5(2) no N1 . C2 . C7 . 118.82(19) no C3 . C2 . C7 . 122.7(2) no C2 . C3 . C4 . 118.0(2) no C2 . C3 . H31 . 121.3 no C4 . C3 . H31 . 120.6 no C3 . C4 . C5 . 120.2(2) no C3 . C4 . C49 . 117.0(2) no C5 . C4 . C49 . 122.8(2) no C4 . C5 . C6 . 120.8(2) no C4 . C5 . H51 . 119.0 no C6 . C5 . H51 . 120.2 no C5 . C6 . C7 . 118.9(2) no C5 . C6 . C8 . 124.1(2) no C7 . C6 . C8 . 116.93(19) no C6 . C7 . C2 . 119.3(2) no C6 . C7 . H71 . 120.1 no C2 . C7 . H71 . 120.6 no C6 . C8 . N9 . 117.07(19) no C6 . C8 . O55 . 120.1(2) no N9 . C8 . O55 . 122.9(2) no C8 . N9 . C10 . 121.32(19) no C8 . N9 . H7 . 117.0 no C10 . N9 . H7 . 121.6 no N9 . C10 . C11 . 113.35(19) no N9 . C10 . H101 . 106.1 no C11 . C10 . H101 . 109.4 no N9 . C10 . H102 . 108.7 no C11 . C10 . H102 . 107.8 no H101 . C10 . H102 . 111.6 no C10 . C11 . O12 . 108.32(19) no C10 . C11 . H111 . 110.6 no O12 . C11 . H111 . 110.2 no C10 . C11 . H112 . 110.4 no O12 . C11 . H112 . 109.3 no H111 . C11 . H112 . 108.0 no C11 . O12 . C13 . 111.38(17) no O12 . C13 . C14 . 110.45(19) no O12 . C13 . H131 . 108.6 no C14 . C13 . H131 . 107.7 no O12 . C13 . H132 . 109.0 no C14 . C13 . H132 . 111.8 no H131 . C13 . H132 . 109.3 no C13 . C14 . O15 . 113.96(17) no C13 . C14 . H141 . 109.1 no O15 . C14 . H141 . 106.6 no C13 . C14 . H142 . 109.1 no O15 . C14 . H142 . 108.4 no H141 . C14 . H142 . 109.6 no C14 . O15 . C16 . 113.58(16) no O15 . C16 . C17 . 118.94(18) no O15 . C16 . C31 . 119.26(19) no C17 . C16 . C31 . 121.7(2) no C16 . C17 . C18 . 123.07(19) no C16 . C17 . C34 . 117.8(2) no C18 . C17 . C34 . 119.02(19) no C17 . C18 . C19 . 109.48(16) no C17 . C18 . H181 . 111.6 no C19 . C18 . H181 . 109.6 no C17 . C18 . H182 . 108.7 no C19 . C18 . H182 . 109.0 no H181 . C18 . H182 . 108.5 no C18 . C19 . C20 . 120.30(18) no C18 . C19 . C53 . 121.33(19) no C20 . C19 . C53 . 118.19(19) no C19 . C20 . C21 . 121.58(18) no C19 . C20 . O54 . 115.30(18) no C21 . C20 . O54 . 123.12(18) no C20 . C21 . C22 . 121.83(18) no C20 . C21 . C51 . 117.80(19) no C22 . C21 . C51 . 120.36(19) no C21 . C22 . C23 . 113.45(17) no C21 . C22 . H221 . 108.1 no C23 . C22 . H221 . 110.7 no C21 . C22 . H222 . 106.3 no C23 . C22 . H222 . 107.5 no H221 . C22 . H222 . 110.7 no C22 . C23 . C24 . 121.0(2) no C22 . C23 . C41 . 121.2(2) no C24 . C23 . C41 . 117.7(2) no C23 . C24 . C25 . 122.2(2) no C23 . C24 . O42 . 117.89(18) no C25 . C24 . O42 . 119.65(18) no C24 . C25 . C26 . 121.76(19) no C24 . C25 . C39 . 117.7(2) no C26 . C25 . C39 . 120.42(19) no C25 . C26 . C27 . 111.64(17) no C25 . C26 . H261 . 109.4 no C27 . C26 . H261 . 109.0 no C25 . C26 . H262 . 108.2 no C27 . C26 . H262 . 109.4 no H261 . C26 . H262 . 109.1 no C26 . C27 . C28 . 119.66(18) no C26 . C27 . C37 . 122.40(19) no C28 . C27 . C37 . 117.9(2) no C27 . C28 . C29 . 121.31(19) no C27 . C28 . O38 . 115.71(19) no C29 . C28 . O38 . 122.97(19) no C28 . C29 . C30 . 120.8(2) no C28 . C29 . C35 . 118.2(2) no C30 . C29 . C35 . 121.1(2) no C29 . C30 . C31 . 112.21(18) no C29 . C30 . H301 . 109.2 no C31 . C30 . H301 . 110.9 no C29 . C30 . H302 . 106.6 no C31 . C30 . H302 . 108.6 no H301 . C30 . H302 . 109.2 no C30 . C31 . C16 . 122.4(2) no C30 . C31 . C32 . 119.8(2) no C16 . C31 . C32 . 117.6(2) no C31 . C32 . C33 . 121.4(2) no C31 . C32 . H321 . 117.2 no C33 . C32 . H321 . 121.4 no C32 . C33 . C34 . 119.5(2) no C32 . C33 . H331 . 120.5 no C34 . C33 . H331 . 120.0 no C17 . C34 . C33 . 121.8(2) no C17 . C34 . H341 . 118.6 no C33 . C34 . H341 . 119.6 no C29 . C35 . C36 . 121.5(2) no C29 . C35 . H351 . 118.1 no C36 . C35 . H351 . 120.3 no C35 . C36 . C37 . 119.4(2) no C35 . C36 . H361 . 120.7 no C37 . C36 . H361 . 119.9 no C27 . C37 . C36 . 121.7(2) no C27 . C37 . H371 . 118.4 no C36 . C37 . H371 . 119.9 no C28 . O38 . H9 . 115.8 no C25 . C39 . C40 . 121.2(2) no C25 . C39 . H391 . 119.2 no C40 . C39 . H391 . 119.7 no C39 . C40 . C41 . 120.1(2) no C39 . C40 . H401 . 119.1 no C41 . C40 . H401 . 120.8 no C23 . C41 . C40 . 121.0(2) no C23 . C41 . H411 . 118.3 no C40 . C41 . H411 . 120.7 no C24 . O42 . C43 . 115.76(16) no O42 . C43 . C44 . 113.31(17) no O42 . C43 . H431 . 107.0 no C44 . C43 . H431 . 108.0 no O42 . C43 . H432 . 108.8 no C44 . C43 . H432 . 110.1 no H431 . C43 . H432 . 109.5 no C43 . C44 . O45 . 107.37(18) no C43 . C44 . H441 . 109.1 no O45 . C44 . H441 . 110.0 no C43 . C44 . H442 . 110.6 no O45 . C44 . H442 . 109.7 no H441 . C44 . H442 . 110.0 no C44 . O45 . C46 . 113.09(17) no O45 . C46 . C47 . 107.98(19) no O45 . C46 . H461 . 108.7 no C47 . C46 . H461 . 109.5 no O45 . C46 . H462 . 111.8 no C47 . C46 . H462 . 110.2 no H461 . C46 . H462 . 108.6 no C46 . C47 . N48 . 113.1(2) no C46 . C47 . H471 . 108.7 no N48 . C47 . H471 . 108.9 no C46 . C47 . H472 . 108.5 no N48 . C47 . H472 . 108.4 no H471 . C47 . H472 . 109.2 no C47 . N48 . C49 . 121.5(2) no C47 . N48 . H3 . 118.3 no C49 . N48 . H3 . 120.2 no C4 . C49 . N48 . 117.0(2) no C4 . C49 . O50 . 119.5(2) no N48 . C49 . O50 . 123.5(2) no C21 . C51 . C52 . 121.7(2) no C21 . C51 . H511 . 117.6 no C52 . C51 . H511 . 120.6 no C51 . C52 . C53 . 119.5(2) no C51 . C52 . H521 . 120.0 no C53 . C52 . H521 . 120.4 no C19 . C53 . C52 . 121.1(2) no C19 . C53 . H531 . 118.3 no C52 . C53 . H531 . 120.5 no C20 . O54 . H6 . 113.0 no H11 . O100 . H12 . 100.1 no C200 2_666 C200 . O201 . 144.5(4) no C200 2_666 C200 . C202 . 108.5(3) no O201 . C200 . C202 . 107.0(3) no O200 2_666 O200 . O201 . 144.9(4) no O200 2_666 O200 . C202 . 108.4(3) no O201 . O200 . C202 . 106.5(3) no C200 . C202 . C203 . 102.7(3) no C200 . C202 . H2021 . 110.1 no C203 . C202 . H2021 . 110.8 no C200 . C202 . H2022 . 112.9 no C203 . C202 . H2022 . 110.5 no H2021 . C202 . H2022 . 109.7 no O200 . C202 . C203 . 102.9(3) no O200 . C202 . H2021 . 109.8 no C203 . C202 . H2021 . 110.8 no O200 . C202 . H2022 . 113.0 no C203 . C202 . H2022 . 110.5 no H2021 . C202 . H2022 . 109.7 no C202 . C203 . H2031 . 107.7 no C202 . C203 . H2032 . 109.1 no H2031 . C203 . H2032 . 109.2 no C202 . C203 . H2033 . 108.1 no H2031 . C203 . H2033 . 109.6 no H2032 . C203 . H2033 . 113.0 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag # tentative C-H...O bonds O54 . H6 . O42 . 173 0.84 1.91 2.737(2) yes O38 . H9 . O15 . 172 0.81 2.08 2.892(2) yes O100 . H11 . O54 . 167 0.85 2.02 2.860(2) yes O100 . H12 . O50 4_565 178 0.83 2.01 2.839(2) yes C30 . H301 . C14 . 123 0.98 2.72 3.344(2) yes C52 . H521 . C33 4_455 144 0.94 2.77 3.564(2) yes #===END