#------------------------------------------------------------------------------ #$Date: 2013-12-28 09:07:06 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/26/1502670.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1502670 loop_ _publ_author_name 'Auzzas, Luciana' 'Larsson, Andreas' 'Matera, Riccardo' 'Baraldi, Annamaria' 'Desch\^enes-Simard, Beno\^it' 'Giannini, Giuseppe' 'Cabri, Walter' 'Battistuzzi, Gianfranco' 'Gallo, Grazia' 'Ciacci, Andrea' 'Vesci, Loredana' 'Pisano, Claudio' 'Hanessian, Stephen' _publ_section_title ; Non-Natural Macrocyclic Inhibitors of Histone Deacetylases: Design, Synthesis, and Activity ; _journal_issue 23 _journal_name_full 'Journal of Medicinal Chemistry' _journal_page_first 8387 _journal_volume 53 _journal_year 2010 _chemical_absolute_configuration rmad _chemical_compound_source 'Synthesized by the authors. See text' _chemical_formula_moiety '2(C26 H31 N O6), C H4 O' _chemical_formula_sum 'C53 H66 N2 O13' _chemical_formula_weight 939.08 _chemical_name_systematic ; ? ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 92.234(1) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.1805(1) _cell_length_b 17.2642(4) _cell_length_c 28.1040(6) _cell_measurement_reflns_used 10900 _cell_measurement_temperature 170 _cell_measurement_theta_max 62.48 _cell_measurement_theta_min 3.00 _cell_volume 2511.63(9) _computing_cell_refinement 'SAINT V7.60A(Bruker AXS, 2008)' _computing_data_collection 'APEX2 (Bruker AXS, 2009)' _computing_data_reduction 'SAINT V7.60A(Bruker AXS, 2008)' _computing_molecular_graphics 'SHELXTL v6.12 (Bruker AXS, 2001)' _computing_publication_material 'UdMX (Maris, 2004)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 170 _diffrn_detector_area_resol_mean 5.5 _diffrn_measured_fraction_theta_full 0.925 _diffrn_measured_fraction_theta_max 0.925 _diffrn_measurement_device_type 'Bruker Smart 6000' _diffrn_measurement_method \w _diffrn_radiation_monochromator 'Montel 200 optics' _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 17480 _diffrn_reflns_theta_full 63.68 _diffrn_reflns_theta_max 63.68 _diffrn_reflns_theta_min 1.57 _exptl_absorpt_coefficient_mu 0.725 _exptl_absorpt_correction_T_max 0.9035 _exptl_absorpt_correction_T_min 0.7869 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs (Sheldrick, 1996)' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1004 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.268 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.029 _refine_ls_abs_structure_details 'Flack H D (1983), 1909 Friedel Pairs' _refine_ls_abs_structure_Flack 0.22(17) _refine_ls_extinction_coef 0.00069(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.917 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 664 _refine_ls_number_reflns 6164 _refine_ls_number_restraints 76 _refine_ls_restrained_S_all 0.944 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_gt 0.0367 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0453P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.0860 _reflns_number_gt 4667 _reflns_number_total 6164 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file jm101092u_si_003.cif _[local]_cod_data_source_block benit8 _[local]_cod_cif_authors_sg_H-M P21 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_geom_bond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (74 times). '_geom_angle_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (92 times). '_geom_torsion_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26 (112 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 1502670 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O11 O 0.7852(3) 0.79666(10) 0.47782(6) 0.0670(5) Uani 1 1 d . . . O12 O 0.2995(4) 1.04409(10) 0.36200(8) 0.0977(7) Uani 1 1 d D . . O13 O 0.7616(3) 0.52275(10) 0.49848(6) 0.0643(5) Uani 1 1 d . . . O14 O 0.4098(3) 0.62737(8) 0.41167(5) 0.0464(4) Uani 1 1 d . A . O15 O -0.4229(3) 0.30668(11) 0.26932(7) 0.0801(6) Uani 1 1 d . A . O16 O -0.2031(4) 0.19733(10) 0.26297(7) 0.0789(6) Uani 1 1 d . A . N11 N 0.6926(3) 0.65215(11) 0.49164(7) 0.0516(5) Uani 1 1 d U . . H11 H 0.5819 0.6859 0.4793 0.062 Uiso 1 1 calc R . . C11 C 0.8994(4) 0.68418(14) 0.51940(8) 0.0515(7) Uani 1 1 d . . . C12 C 1.0445(5) 0.64451(16) 0.55291(8) 0.0568(7) Uani 1 1 d . . . H12 H 1.0059 0.5920 0.5597 0.068 Uiso 1 1 calc R . . C13 C 1.2500(5) 0.68166(18) 0.57703(9) 0.0705(9) Uani 1 1 d . . . H13 H 1.3514 0.6545 0.6005 0.085 Uiso 1 1 calc RD . . C14 C 1.3057(5) 0.75777(17) 0.56685(10) 0.0689(9) Uani 1 1 d U . . H14 H 1.4478 0.7823 0.5831 0.083 Uiso 1 1 calc R . . C15 C 1.1585(5) 0.79921(17) 0.53342(10) 0.0646(8) Uani 1 1 d U . . H15 H 1.1997 0.8516 0.5266 0.078 Uiso 1 1 calc R . . C16 C 0.9509(5) 0.76338(15) 0.51019(9) 0.0548(7) Uani 1 1 d . . . C17 C 0.8395(5) 0.86907(14) 0.45666(9) 0.0612(7) Uani 1 1 d U . . H17A H 1.0122 0.8682 0.4428 0.073 Uiso 1 1 calc R . . H17B H 0.8363 0.9110 0.4807 0.073 Uiso 1 1 calc R . . C18 C 0.6343(5) 0.88181(14) 0.41867(9) 0.0557(7) Uani 1 1 d U A . C19 C 0.5517(5) 0.95632(15) 0.40687(10) 0.0688(8) Uani 1 1 d U . . H19 H 0.6248 0.9997 0.4233 0.083 Uiso 1 1 calc R A . C110 C 0.3632(6) 0.96723(16) 0.37128(10) 0.0709(7) Uani 1 1 d DU A . C111 C 0.2479(5) 0.90603(15) 0.34831(9) 0.0647(8) Uani 1 1 d U . . H111 H 0.1166 0.9146 0.3243 0.078 Uiso 1 1 calc R A . C112 C 0.3246(5) 0.82976(15) 0.36033(9) 0.0580(7) Uani 1 1 d . A . C113 C 0.5225(5) 0.81975(14) 0.39432(8) 0.0523(7) Uani 1 1 d . . . H113 H 0.5835 0.7689 0.4011 0.063 Uiso 1 1 calc R A . C114 C 0.2011(5) 0.76470(15) 0.33567(10) 0.0643(8) Uani 1 1 d . . . H114 H 0.1562 0.7723 0.3029 0.077 Uiso 1 1 calc R A . C115 C 0.1433(5) 0.69540(15) 0.35368(9) 0.0601(8) Uani 1 1 d . A . H115 H 0.0774 0.6579 0.3317 0.072 Uiso 1 1 calc R . . C116 C 0.1704(4) 0.67075(14) 0.40393(9) 0.0531(7) Uani 1 1 d . . . H11C H 0.1718 0.7168 0.4249 0.064 Uiso 1 1 calc R A . H11D H 0.0216 0.6379 0.4119 0.064 Uiso 1 1 calc R . . C117 C 0.6399(4) 0.57722(15) 0.48130(8) 0.0478(6) Uani 1 1 d U A . C118 C 0.4096(4) 0.56666(13) 0.44662(8) 0.0446(6) Uani 1 1 d . . . H118 H 0.2480 0.5711 0.4648 0.054 Uiso 1 1 calc R A . C119 C 0.4102(4) 0.48840(13) 0.42236(9) 0.0483(7) Uani 1 1 d . A . H11A H 0.4249 0.4477 0.4471 0.058 Uiso 1 1 calc R . . H11B H 0.5652 0.4849 0.4030 0.058 Uiso 1 1 calc R . . C120 C 0.1729(4) 0.47193(13) 0.39053(9) 0.0487(7) Uani 1 1 d . . . H12G H 0.0170 0.4748 0.4098 0.058 Uiso 1 1 calc R A . H12H H 0.1573 0.5123 0.3655 0.058 Uiso 1 1 calc R . . C121 C 0.1843(4) 0.39301(13) 0.36711(9) 0.0486(7) Uani 1 1 d . A . H12C H 0.2020 0.3532 0.3924 0.058 Uiso 1 1 calc R . . H12D H 0.3413 0.3906 0.3482 0.058 Uiso 1 1 calc R . . C122 C -0.0487(4) 0.37268(13) 0.33471(8) 0.0449(6) Uani 1 1 d . . . H12A H -0.2075 0.3755 0.3531 0.054 Uiso 1 1 calc R A . H12B H -0.0647 0.4110 0.3085 0.054 Uiso 1 1 calc R . . C123 C -0.0235(4) 0.29208(13) 0.31390(8) 0.0489(7) Uani 1 1 d . A . H12E H 0.1404 0.2894 0.2970 0.059 Uiso 1 1 calc R . . H12F H -0.0114 0.2544 0.3404 0.059 Uiso 1 1 calc R . . C124 C -0.2372(5) 0.26811(14) 0.28055(8) 0.0475(7) Uani 1 1 d . . . C125 C -0.4010(6) 0.16812(18) 0.23034(11) 0.0940(11) Uani 1 1 d . . . H12I H -0.5661 0.1664 0.2462 0.141 Uiso 1 1 calc R A . H12J H -0.3547 0.1158 0.2201 0.141 Uiso 1 1 calc RD . . H12K H -0.4170 0.2023 0.2025 0.141 Uiso 1 1 calc R . . C126 C 0.181(4) 1.0570(10) 0.3140(6) 0.1031(15) Uani 0.134(7) 1 d PD A 1 H12L H 0.2556 1.0206 0.2915 0.155 Uiso 0.134(7) 1 calc PR A 1 H12M H 0.2159 1.1102 0.3038 0.155 Uiso 0.134(7) 1 calc PR A 1 H12N H -0.0056 1.0488 0.3147 0.155 Uiso 0.134(7) 1 calc PR A 1 C127 C 0.0921(9) 1.0588(2) 0.32757(15) 0.1031(15) Uani 0.866(7) 1 d PD A 2 H12O H -0.0682 1.0362 0.3388 0.155 Uiso 0.866(7) 1 calc PR A 2 H12P H 0.1333 1.0353 0.2970 0.155 Uiso 0.866(7) 1 calc PR A 2 H12Q H 0.0700 1.1148 0.3235 0.155 Uiso 0.866(7) 1 calc PR A 2 O21 O -0.3304(3) 0.11757(11) -0.08119(6) 0.0745(6) Uani 1 1 d . . . O22 O 0.1820(4) 0.27826(13) -0.23653(6) 0.0914(7) Uani 1 1 d . . . O23 O -0.2186(4) 0.07331(12) 0.08585(7) 0.0948(7) Uani 1 1 d . . . O24 O 0.0282(3) 0.23302(9) 0.02106(5) 0.0469(4) Uani 1 1 d . . . O25 O 0.6586(3) 0.51546(10) 0.20948(6) 0.0582(5) Uani 1 1 d . . . O26 O 0.4340(3) 0.53057(10) 0.27513(6) 0.0620(5) Uani 1 1 d . . . N21 N -0.2570(3) 0.10865(11) 0.00888(7) 0.0503(5) Uani 1 1 d . . . H21 H -0.1868 0.1401 -0.0116 0.060 Uiso 1 1 calc R . . C21 C -0.4494(4) 0.05951(13) -0.01136(9) 0.0465(7) Uani 1 1 d . . . C22 C -0.5989(4) 0.00997(14) 0.01395(10) 0.0564(7) Uani 1 1 d . . . H22 H -0.5730 0.0052 0.0475 0.068 Uiso 1 1 calc R . . C23 C -0.7898(5) -0.03349(16) -0.01032(11) 0.0694(9) Uani 1 1 d U . . H23 H -0.8926 -0.0685 0.0069 0.083 Uiso 1 1 calc R . . C24 C -0.8304(5) -0.02620(16) -0.05838(11) 0.0699(9) Uani 1 1 d U . . H24 H -0.9618 -0.0560 -0.0742 0.084 Uiso 1 1 calc R . . C25 C -0.6834(4) 0.02368(14) -0.08406(10) 0.0581(7) Uani 1 1 d U . . H25 H -0.7130 0.0289 -0.1175 0.070 Uiso 1 1 calc R . . C26 C -0.4929(4) 0.06586(14) -0.06068(9) 0.0525(7) Uani 1 1 d . . . C27 C -0.3626(5) 0.13962(16) -0.12894(9) 0.0612(8) Uani 1 1 d . . . H27A H -0.5381 0.1608 -0.1353 0.073 Uiso 1 1 calc R . . H27B H -0.3385 0.0945 -0.1501 0.073 Uiso 1 1 calc R . . C28 C -0.1617(5) 0.20055(14) -0.13766(9) 0.0563(7) Uani 1 1 d . . . C29 C -0.0712(5) 0.21209(15) -0.18286(9) 0.0642(8) Uani 1 1 d . . . H29 H -0.1340 0.1810 -0.2087 0.077 Uiso 1 1 calc R . . C210 C 0.1122(5) 0.26943(17) -0.19023(9) 0.0640(8) Uani 1 1 d . . . C211 C 0.2103(5) 0.31281(15) -0.15270(9) 0.0623(7) Uani 1 1 d U . . H211 H 0.3361 0.3515 -0.1582 0.075 Uiso 1 1 calc RD . . C212 C 0.1280(5) 0.30085(14) -0.10683(9) 0.0517(7) Uani 1 1 d U . . C213 C -0.0671(5) 0.24614(14) -0.09993(9) 0.0553(7) Uani 1 1 d . . . H213 H -0.1354 0.2401 -0.0693 0.066 Uiso 1 1 calc R . . C214 C 0.2353(5) 0.34659(14) -0.06697(9) 0.0607(8) Uani 1 1 d . . . H214 H 0.2731 0.3993 -0.0735 0.073 Uiso 1 1 calc R . . C215 C 0.2862(4) 0.32263(14) -0.02248(10) 0.0571(8) Uani 1 1 d . . . H215 H 0.3415 0.3613 -0.0003 0.069 Uiso 1 1 calc R . . C216 C 0.2666(4) 0.24290(14) -0.00364(8) 0.0502(7) Uani 1 1 d . . . H21A H 0.2720 0.2054 -0.0302 0.060 Uiso 1 1 calc R . . H21B H 0.4155 0.2323 0.0186 0.060 Uiso 1 1 calc R . . C217 C -0.1634(5) 0.11595(15) 0.05308(9) 0.0532(7) Uani 1 1 d . . . C218 C 0.0344(4) 0.18167(13) 0.06105(8) 0.0467(7) Uani 1 1 d . . . H218 H 0.2110 0.1586 0.0648 0.056 Uiso 1 1 calc R . . C219 C -0.0223(4) 0.22693(15) 0.10595(8) 0.0504(7) Uani 1 1 d . . . H21C H -0.1904 0.2536 0.1012 0.060 Uiso 1 1 calc R . . H21D H -0.0373 0.1902 0.1328 0.060 Uiso 1 1 calc R . . C220 C 0.1835(4) 0.28622(14) 0.11895(8) 0.0470(7) Uani 1 1 d . . . H22C H 0.2059 0.3209 0.0914 0.056 Uiso 1 1 calc R . . H22D H 0.3494 0.2591 0.1255 0.056 Uiso 1 1 calc R . . C221 C 0.1217(4) 0.33506(14) 0.16202(9) 0.0507(7) Uani 1 1 d . . . H22A H -0.0470 0.3609 0.1560 0.061 Uiso 1 1 calc R . . H22B H 0.1055 0.3006 0.1899 0.061 Uiso 1 1 calc R . . C222 C 0.3248(4) 0.39609(14) 0.17374(8) 0.0494(7) Uani 1 1 d . . . H22E H 0.3373 0.4314 0.1462 0.059 Uiso 1 1 calc R . . H22F H 0.4944 0.3704 0.1789 0.059 Uiso 1 1 calc R . . C223 C 0.2666(4) 0.44368(14) 0.21789(8) 0.0504(7) Uani 1 1 d . . . H22G H 0.1047 0.4730 0.2116 0.060 Uiso 1 1 calc R . . H22H H 0.2379 0.4079 0.2447 0.060 Uiso 1 1 calc R . . C224 C 0.4746(4) 0.49874(14) 0.23223(9) 0.0464(7) Uani 1 1 d . . . C225 C 0.6311(5) 0.58408(16) 0.29229(10) 0.0695(9) Uani 1 1 d . . . H22I H 0.8003 0.5587 0.2922 0.104 Uiso 1 1 calc R . . H22J H 0.5947 0.6002 0.3248 0.104 Uiso 1 1 calc R . . H22K H 0.6321 0.6296 0.2715 0.104 Uiso 1 1 calc R . . C226 C 0.3498(6) 0.3406(2) -0.24731(11) 0.1020(12) Uani 1 1 d . . . H22L H 0.2709 0.3897 -0.2381 0.153 Uiso 1 1 calc R . . H22M H 0.3786 0.3411 -0.2816 0.153 Uiso 1 1 calc R . . H22N H 0.5153 0.3340 -0.2297 0.153 Uiso 1 1 calc R . . O31A O 0.156(4) 0.9619(9) 0.2131(2) 0.185(5) Uani 0.20 1 d PDU B 3 H31A H 0.0654 0.9943 0.2273 0.277 Uiso 0.20 1 calc PR B 3 C31A C 0.144(4) 0.9784(12) 0.1625(3) 0.131(3) Uani 0.20 1 d PDU B 3 H31C H -0.0089 1.0099 0.1546 0.196 Uiso 0.20 1 calc PR B 3 H31D H 0.1344 0.9297 0.1446 0.196 Uiso 0.20 1 calc PR B 3 H31E H 0.2997 1.0069 0.1541 0.196 Uiso 0.20 1 calc PR B 3 O31B O -0.0108(7) 1.0234(3) 0.17548(17) 0.1274(15) Uani 0.50 1 d PDU C 4 H31B H -0.1210 0.9891 0.1686 0.191 Uiso 0.50 1 calc PR C 4 C31B C 0.2488(8) 0.9940(4) 0.1662(3) 0.117(2) Uani 0.50 1 d PDU C 4 H31F H 0.3519 1.0355 0.1526 0.176 Uiso 0.50 1 calc PR C 4 H31G H 0.2349 0.9507 0.1437 0.176 Uiso 0.50 1 calc PR C 4 H31H H 0.3325 0.9762 0.1961 0.176 Uiso 0.50 1 calc PR C 4 O31C O 0.2524(10) 1.0450(5) 0.1501(3) 0.183(3) Uani 0.30 1 d PDU D 5 H31I H 0.2138 1.0430 0.1208 0.275 Uiso 0.30 1 calc PR D 5 C31C C 0.4975(10) 1.0055(5) 0.1596(4) 0.115(3) Uani 0.30 1 d PDU D 5 H31J H 0.4990 0.9825 0.1915 0.172 Uiso 0.30 1 calc PR D 5 H31K H 0.6394 1.0428 0.1579 0.172 Uiso 0.30 1 calc PR D 5 H31L H 0.5190 0.9647 0.1359 0.172 Uiso 0.30 1 calc PR D 5 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 O11 0.0666(11) 0.0577(11) 0.0760(12) 0.0056(9) -0.0083(10) -0.0142(9) O12 0.1388(17) 0.0483(12) 0.1071(16) 0.0065(11) 0.0202(14) 0.0278(12) O13 0.0753(11) 0.0560(11) 0.0603(11) 0.0017(9) -0.0141(10) 0.0024(9) O14 0.0410(8) 0.0469(10) 0.0512(9) 0.0015(8) 0.0032(8) 0.0007(7) O15 0.0544(10) 0.0887(14) 0.0958(14) -0.0282(11) -0.0154(10) 0.0193(10) O16 0.0961(13) 0.0495(11) 0.0889(13) -0.0164(10) -0.0274(12) 0.0089(10) N11 0.0434(11) 0.0502(9) 0.0608(13) -0.0065(10) -0.0038(10) -0.0042(9) C11 0.0502(14) 0.0618(18) 0.0425(14) -0.0108(13) 0.0039(13) -0.0052(13) C12 0.0575(15) 0.0668(17) 0.0461(15) -0.0109(13) 0.0043(14) -0.0009(14) C13 0.0655(17) 0.095(2) 0.0504(17) -0.0188(16) -0.0016(15) 0.0008(17) C14 0.0523(16) 0.086(2) 0.0679(18) -0.0362(16) 0.0008(15) -0.0126(14) C15 0.0574(16) 0.0672(18) 0.0697(18) -0.0210(15) 0.0072(15) -0.0125(14) C16 0.0534(15) 0.0624(18) 0.0489(15) -0.0148(13) 0.0060(14) -0.0100(13) C17 0.0701(14) 0.0473(16) 0.0672(15) -0.0085(14) 0.0158(10) -0.0047(13) C18 0.0647(14) 0.0421(15) 0.0618(15) -0.0046(13) 0.0216(10) -0.0032(12) C19 0.0859(16) 0.0506(17) 0.0714(17) -0.0086(14) 0.0223(11) 0.0019(14) C110 0.0962(18) 0.0469(14) 0.0712(18) 0.0067(11) 0.0228(11) 0.0160(12) C111 0.0753(17) 0.0546(15) 0.0649(18) 0.0092(12) 0.0118(14) 0.0191(12) C112 0.0636(16) 0.0551(17) 0.0561(16) -0.0020(13) 0.0122(14) 0.0122(14) C113 0.0604(15) 0.0448(16) 0.0525(16) -0.0051(12) 0.0122(14) 0.0058(13) C114 0.0706(17) 0.0622(19) 0.0594(16) 0.0030(15) -0.0053(15) 0.0115(14) C115 0.0599(16) 0.0543(17) 0.0651(18) -0.0075(14) -0.0082(15) 0.0094(14) C116 0.0419(13) 0.0491(15) 0.0685(18) -0.0002(13) 0.0043(13) 0.0023(12) C117 0.0456(13) 0.0495(10) 0.0486(15) -0.0033(12) 0.0049(13) -0.0046(12) C118 0.0430(13) 0.0432(14) 0.0482(15) -0.0020(12) 0.0091(12) -0.0024(11) C119 0.0377(12) 0.0452(15) 0.0621(16) -0.0055(12) 0.0041(12) 0.0006(11) C120 0.0375(12) 0.0435(14) 0.0652(16) -0.0070(12) 0.0029(13) -0.0019(11) C121 0.0385(13) 0.0430(15) 0.0645(16) -0.0055(12) 0.0045(13) -0.0004(11) C122 0.0374(12) 0.0439(14) 0.0537(14) -0.0021(12) 0.0057(12) 0.0020(11) C123 0.0465(13) 0.0419(14) 0.0583(16) -0.0005(12) 0.0009(13) 0.0054(11) C124 0.0441(14) 0.0480(16) 0.0507(15) -0.0014(12) 0.0043(13) -0.0033(12) C125 0.109(2) 0.077(2) 0.094(2) -0.0275(18) -0.019(2) -0.0218(19) C126 0.149(4) 0.072(2) 0.089(3) 0.022(2) 0.013(3) 0.057(2) C127 0.149(4) 0.072(2) 0.089(3) 0.022(2) 0.013(3) 0.057(2) O21 0.0732(11) 0.0931(14) 0.0564(11) 0.0096(10) -0.0076(10) -0.0361(11) O22 0.1040(15) 0.1249(17) 0.0456(11) 0.0100(12) 0.0064(11) -0.0185(14) O23 0.1381(17) 0.0803(14) 0.0652(13) 0.0153(11) -0.0061(13) -0.0417(13) O24 0.0445(9) 0.0469(9) 0.0496(9) 0.0029(8) 0.0046(8) 0.0054(8) O25 0.0475(9) 0.0712(11) 0.0562(11) -0.0072(9) 0.0061(9) -0.0045(9) O26 0.0619(10) 0.0683(12) 0.0564(11) -0.0215(9) 0.0092(9) -0.0046(9) N21 0.0511(11) 0.0472(12) 0.0524(13) 0.0004(10) 0.0015(11) -0.0039(10) C21 0.0379(13) 0.0357(14) 0.0659(17) -0.0051(12) 0.0040(13) 0.0027(11) C22 0.0549(14) 0.0422(15) 0.0729(18) -0.0005(14) 0.0145(14) 0.0049(12) C23 0.0583(16) 0.0526(17) 0.098(2) -0.0043(16) 0.0139(17) -0.0124(14) C24 0.0544(16) 0.0611(18) 0.095(2) -0.0212(16) 0.0079(17) -0.0090(14) C25 0.0482(14) 0.0539(16) 0.0727(18) -0.0160(14) 0.0074(14) -0.0038(13) C26 0.0457(14) 0.0485(15) 0.0637(17) -0.0077(14) 0.0061(14) -0.0036(13) C27 0.0671(17) 0.0645(18) 0.0509(16) -0.0047(14) -0.0106(14) -0.0038(14) C28 0.0566(15) 0.0591(17) 0.0529(16) 0.0009(14) -0.0028(14) 0.0015(13) C29 0.0762(18) 0.071(2) 0.0447(16) -0.0013(14) -0.0052(15) -0.0001(15) C210 0.0714(17) 0.079(2) 0.0412(15) 0.0071(14) 0.0021(14) -0.0021(15) C211 0.0694(16) 0.0641(18) 0.0539(11) 0.0098(14) 0.0080(13) -0.0046(14) C212 0.0611(15) 0.0444(15) 0.0499(11) 0.0022(12) 0.0058(12) -0.0008(13) C213 0.0655(16) 0.0481(16) 0.0527(16) -0.0078(13) 0.0068(14) 0.0006(13) C214 0.0762(18) 0.0468(16) 0.0599(18) -0.0004(13) 0.0143(15) -0.0133(13) C215 0.0551(15) 0.0498(17) 0.0673(18) -0.0083(14) 0.0138(14) -0.0126(12) C216 0.0431(13) 0.0517(16) 0.0564(16) -0.0084(13) 0.0102(13) 0.0020(12) C217 0.0633(16) 0.0483(15) 0.0482(16) 0.0021(13) 0.0044(14) 0.0006(13) C218 0.0464(13) 0.0465(15) 0.0472(15) 0.0016(12) 0.0003(13) 0.0035(12) C219 0.0454(14) 0.0584(16) 0.0475(15) -0.0057(13) 0.0036(12) 0.0011(13) C220 0.0417(13) 0.0549(15) 0.0446(14) -0.0026(12) 0.0025(12) 0.0018(12) C221 0.0417(13) 0.0614(16) 0.0494(16) -0.0029(13) 0.0065(13) 0.0014(12) C222 0.0453(14) 0.0568(16) 0.0462(15) -0.0041(12) 0.0039(12) -0.0024(12) C223 0.0417(13) 0.0602(16) 0.0501(15) -0.0072(12) 0.0105(12) 0.0026(12) C224 0.0405(13) 0.0514(16) 0.0469(15) -0.0033(13) -0.0042(13) 0.0102(12) C225 0.0697(17) 0.0687(19) 0.0698(19) -0.0224(15) -0.0019(16) -0.0023(15) C226 0.093(2) 0.146(3) 0.068(2) 0.032(2) 0.0164(19) -0.020(2) O31A 0.193(9) 0.202(9) 0.1604(16) 0.018(5) 0.011(7) -0.019(7) C31A 0.123(6) 0.109(6) 0.160(3) 0.008(5) -0.013(6) -0.021(6) O31B 0.1622(16) 0.129(3) 0.092(3) 0.002(3) 0.023(3) 0.033(3) C31B 0.112(3) 0.099(4) 0.139(4) 0.016(4) -0.021(4) -0.006(3) O31C 0.1947(19) 0.185(5) 0.168(6) 0.014(5) -0.029(5) 0.019(3) C31C 0.149(4) 0.087(5) 0.111(6) -0.010(5) 0.034(5) -0.027(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C16 O11 C17 121.7(2) y C110 O12 C127 117.4(3) y C110 O12 C126 113.7(7) y C127 O12 C126 24.2(9) y C118 O14 C116 116.97(16) y C124 O16 C125 117.1(2) y C117 N11 C11 129.5(2) y C117 N11 H11 115.3 ? C11 N11 H11 115.3 ? C12 C11 N11 124.7(2) y C12 C11 C16 120.4(2) y N11 C11 C16 114.9(2) y C11 C12 C13 119.6(3) y C11 C12 H12 120.2 ? C13 C12 H12 120.2 ? C14 C13 C12 120.0(3) y C14 C13 H13 120 ? C12 C13 H13 120 ? C13 C14 C15 121.3(3) y C13 C14 H14 119.4 ? C15 C14 H14 119.4 ? C16 C15 C14 119.1(3) y C16 C15 H15 120.4 ? C14 C15 H15 120.4 ? O11 C16 C15 126.0(2) y O11 C16 C11 114.4(2) y C15 C16 C11 119.6(2) y O11 C17 C18 106.4(2) y O11 C17 H17A 110.4 ? C18 C17 H17A 110.4 ? O11 C17 H17B 110.4 ? C18 C17 H17B 110.4 ? H17A C17 H17B 108.6 ? C113 C18 C19 118.6(2) y C113 C18 C17 120.7(2) y C19 C18 C17 120.7(2) y C110 C19 C18 120.0(3) y C110 C19 H19 120 ? C18 C19 H19 120 ? C111 C110 C19 121.4(2) y C111 C110 O12 123.7(3) y C19 C110 O12 114.9(3) y C110 C111 C112 119.7(3) y C110 C111 H111 120.2 ? C112 C111 H111 120.2 ? C113 C112 C111 118.4(2) y C113 C112 C114 122.2(2) y C111 C112 C114 119.4(2) y C112 C113 C18 121.9(2) y C112 C113 H113 119.1 ? C18 C113 H113 119.1 ? C115 C114 C112 127.7(3) y C115 C114 H114 116.2 ? C112 C114 H114 116.2 ? C114 C115 C116 127.3(2) y C114 C115 H115 116.4 ? C116 C115 H115 116.4 ? O14 C116 C115 109.84(19) y O14 C116 H11C 109.7 ? C115 C116 H11C 109.7 ? O14 C116 H11D 109.7 ? C115 C116 H11D 109.7 ? H11C C116 H11D 108.2 ? O13 C117 N11 123.7(2) y O13 C117 C118 122.7(2) y N11 C117 C118 113.5(2) y O14 C118 C119 110.08(18) y O14 C118 C117 109.21(18) y C119 C118 C117 112.33(19) y O14 C118 H118 108.4 ? C119 C118 H118 108.4 ? C117 C118 H118 108.4 ? C118 C119 C120 114.62(18) y C118 C119 H11A 108.6 ? C120 C119 H11A 108.6 ? C118 C119 H11B 108.6 ? C120 C119 H11B 108.6 ? H11A C119 H11B 107.6 ? C121 C120 C119 112.32(18) y C121 C120 H12G 109.1 ? C119 C120 H12G 109.1 ? C121 C120 H12H 109.1 ? C119 C120 H12H 109.1 ? H12G C120 H12H 107.9 ? C120 C121 C122 115.03(19) y C120 C121 H12C 108.5 ? C122 C121 H12C 108.5 ? C120 C121 H12D 108.5 ? C122 C121 H12D 108.5 ? H12C C121 H12D 107.5 ? C123 C122 C121 111.31(18) y C123 C122 H12A 109.4 ? C121 C122 H12A 109.4 ? C123 C122 H12B 109.4 ? C121 C122 H12B 109.4 ? H12A C122 H12B 108 ? C124 C123 C122 115.26(19) y C124 C123 H12E 108.5 ? C122 C123 H12E 108.5 ? C124 C123 H12F 108.5 ? C122 C123 H12F 108.5 ? H12E C123 H12F 107.5 ? O15 C124 O16 121.8(2) y O15 C124 C123 125.6(2) y O16 C124 C123 112.6(2) y O16 C125 H12I 109.5 ? O16 C125 H12J 109.5 ? H12I C125 H12J 109.5 ? O16 C125 H12K 109.5 ? H12I C125 H12K 109.5 ? H12J C125 H12K 109.5 ? O12 C126 H12L 109.5 ? O12 C126 H12M 109.5 ? O12 C126 H12N 109.5 ? O12 C127 H12O 109.5 ? O12 C127 H12P 109.5 ? H12O C127 H12P 109.5 ? O12 C127 H12Q 109.5 ? H12O C127 H12Q 109.5 ? H12P C127 H12Q 109.5 ? C26 O21 C27 121.95(19) y C210 O22 C226 118.1(2) y C218 O24 C216 117.09(17) y C224 O26 C225 115.19(19) y C217 N21 C21 131.6(2) y C217 N21 H21 114.2 ? C21 N21 H21 114.2 ? C22 C21 C26 119.4(2) y C22 C21 N21 124.7(2) y C26 C21 N21 115.8(2) y C21 C22 C23 119.0(3) y C21 C22 H22 120.5 ? C23 C22 H22 120.5 ? C24 C23 C22 120.8(3) y C24 C23 H23 119.6 ? C22 C23 H23 119.6 ? C23 C24 C25 120.7(3) y C23 C24 H24 119.6 ? C25 C24 H24 119.6 ? C24 C25 C26 119.0(3) y C24 C25 H25 120.5 ? C26 C25 H25 120.5 ? O21 C26 C25 125.9(2) y O21 C26 C21 113.0(2) y C25 C26 C21 121.1(2) y O21 C27 C28 106.8(2) y O21 C27 H27A 110.4 ? C28 C27 H27A 110.4 ? O21 C27 H27B 110.4 ? C28 C27 H27B 110.4 ? H27A C27 H27B 108.6 ? C29 C28 C213 119.7(2) y C29 C28 C27 120.7(2) y C213 C28 C27 119.7(2) y C28 C29 C210 119.7(2) y C28 C29 H29 120.2 ? C210 C29 H29 120.2 ? O22 C210 C211 124.3(3) y O22 C210 C29 115.2(2) y C211 C210 C29 120.5(2) y C210 C211 C212 120.9(2) y C210 C211 H211 119.6 ? C212 C211 H211 119.6 ? C211 C212 C213 118.5(2) y C211 C212 C214 120.6(2) y C213 C212 C214 120.8(2) y C28 C213 C212 120.6(2) y C28 C213 H213 119.7 ? C212 C213 H213 119.7 ? C215 C214 C212 127.3(2) y C215 C214 H214 116.3 ? C212 C214 H214 116.4 ? C214 C215 C216 127.6(2) y C214 C215 H215 116.2 ? C216 C215 H215 116.2 ? O24 C216 C215 110.63(19) y O24 C216 H21A 109.5 ? C215 C216 H21A 109.5 ? O24 C216 H21B 109.5 ? C215 C216 H21B 109.5 ? H21A C216 H21B 108.1 ? O23 C217 N21 124.3(2) y O23 C217 C218 120.6(2) y N21 C217 C218 115.1(2) y O24 C218 C219 109.50(19) y O24 C218 C217 110.36(19) y C219 C218 C217 110.49(19) y O24 C218 H218 108.8 ? C219 C218 H218 108.8 ? C217 C218 H218 108.8 ? C220 C219 C218 113.00(18) y C220 C219 H21C 109 ? C218 C219 H21C 109 ? C220 C219 H21D 109 ? C218 C219 H21D 109 ? H21C C219 H21D 107.8 ? C219 C220 C221 113.57(18) y C219 C220 H22C 108.9 ? C221 C220 H22C 108.9 ? C219 C220 H22D 108.9 ? C221 C220 H22D 108.9 ? H22C C220 H22D 107.7 ? C222 C221 C220 113.14(18) y C222 C221 H22A 109 ? C220 C221 H22A 109 ? C222 C221 H22B 109 ? C220 C221 H22B 109 ? H22A C221 H22B 107.8 ? C221 C222 C223 113.15(18) y C221 C222 H22E 108.9 ? C223 C222 H22E 108.9 ? C221 C222 H22F 108.9 ? C223 C222 H22F 108.9 ? H22E C222 H22F 107.8 ? C224 C223 C222 113.68(19) y C224 C223 H22G 108.8 ? C222 C223 H22G 108.8 ? C224 C223 H22H 108.8 ? C222 C223 H22H 108.8 ? H22G C223 H22H 107.7 ? O25 C224 O26 122.1(2) y O25 C224 C223 126.3(2) y O26 C224 C223 111.6(2) y O26 C225 H22I 109.5 ? O26 C225 H22J 109.5 ? H22I C225 H22J 109.5 ? O26 C225 H22K 109.5 ? H22I C225 H22K 109.5 ? H22J C225 H22K 109.5 ? O22 C226 H22L 109.5 ? O22 C226 H22M 109.5 ? H22L C226 H22M 109.5 ? O22 C226 H22N 109.5 ? H22L C226 H22N 109.5 ? H22M C226 H22N 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O11 C16 1.354(3) y O11 C17 1.417(3) y O12 C110 1.389(3) y O12 C127 1.440(4) y O12 C126 1.477(12) y O13 C117 1.221(3) y O14 C118 1.436(3) y O14 C116 1.458(3) y O15 C124 1.202(3) y O16 C124 1.332(3) y O16 C125 1.440(3) y N11 C117 1.351(3) y N11 C11 1.413(3) y N11 H11 0.88 ? C11 C12 1.366(3) y C11 C16 1.419(3) y C12 C13 1.396(3) y C12 H12 0.95 ? C13 C14 1.378(4) y C13 H13 0.95 ? C14 C15 1.386(4) y C14 H14 0.95 ? C15 C16 1.382(3) y C15 H15 0.95 ? C17 C18 1.493(3) y C17 H17a 0.99 ? C17 H17b 0.99 ? C18 C113 1.386(3) y C18 C19 1.392(3) y C19 C110 1.383(4) y C19 H19 0.95 ? C110 C111 1.364(4) y C111 C112 1.413(3) y C111 H111 0.95 ? C112 C113 1.385(3) y C112 C114 1.455(4) y C113 H113 0.95 ? C114 C115 1.338(3) y C114 H114 0.95 ? C115 C116 1.476(3) y C115 H115 0.95 ? C116 H11c 0.99 ? C116 H11d 0.99 ? C117 C118 1.522(3) y C118 C119 1.513(3) y C118 H118 1 ? C119 C120 1.519(3) y C119 H11a 0.99 ? C119 H11b 0.99 ? C120 C121 1.515(3) y C120 H12g 0.99 ? C120 H12h 0.99 ? C121 C122 1.524(3) y C121 H12c 0.99 ? C121 H12d 0.99 ? C122 C123 1.517(3) y C122 H12a 0.99 ? C122 H12b 0.99 ? C123 C124 1.481(3) y C123 H12e 0.99 ? C123 H12f 0.99 ? C125 H12i 0.98 ? C125 H12j 0.98 ? C125 H12k 0.98 ? C126 H12l 0.98 ? C126 H12m 0.98 ? C126 H12n 0.98 ? C127 H12o 0.98 ? C127 H12p 0.98 ? C127 H12q 0.98 ? O21 C26 1.369(3) y O21 C27 1.399(3) y O22 C210 1.373(3) y O22 C226 1.424(4) y O23 C217 1.222(3) y O24 C218 1.431(3) y O24 C216 1.450(3) y O25 C224 1.203(3) y O26 C224 1.349(3) y O26 C225 1.446(3) y N21 C217 1.322(3) y N21 C21 1.412(3) y N21 H21 0.88 ? C21 C22 1.371(3) y C21 C26 1.400(3) y C22 C23 1.398(4) y C22 H22 0.95 ? C23 C24 1.365(4) y C23 H23 0.95 ? C24 C25 1.373(4) y C24 H24 0.95 ? C25 C26 1.373(3) y C25 H25 0.95 ? C27 C28 1.507(4) y C27 H27a 0.99 ? C27 H27b 0.99 ? C28 C29 1.385(3) y C28 C213 1.394(3) y C29 C210 1.393(4) y C29 H29 0.95 ? C210 C211 1.375(4) y C211 C212 1.389(3) y C211 H211 0.95 ? C212 C213 1.402(3) y C212 C214 1.463(3) y C213 H213 0.95 ? C214 C215 1.333(3) y C214 H214 0.95 ? C215 C216 1.480(3) y C215 H215 0.95 ? C216 H21a 0.99 ? C216 H21b 0.99 ? C217 C218 1.539(3) y C218 C219 1.522(3) y C218 H218 1 ? C219 C220 1.512(3) y C219 H21c 0.99 ? C219 H21d 0.99 ? C220 C221 1.519(3) y C220 H22c 0.99 ? C220 H22d 0.99 ? C221 C222 1.516(3) y C221 H22a 0.99 ? C221 H22b 0.99 ? C222 C223 1.528(3) y C222 H22e 0.99 ? C222 H22f 0.99 ? C223 C224 1.481(3) y C223 H22g 0.99 ? C223 H22h 0.99 ? C225 H22i 0.98 ? C225 H22j 0.98 ? C225 H22k 0.98 ? C226 H22l 0.98 ? C226 H22m 0.98 ? C226 H22n 0.98 ? O31a C31a 1.448(4) y O31a H31a 0.84 ? C31a H31c 0.98 ? C31a H31d 0.98 ? C31a H31e 0.98 ? O31b C31b 1.470(5) y O31b H31b 0.84 ? C31b H31f 0.98 ? C31b H31g 0.98 ? C31b H31h 0.98 ? O31c C31c 1.457(5) y O31c H31i 0.84 ? C31c H31j 0.98 ? C31c H31k 0.98 ? C31c H31l 0.98 ? 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 N21 H21 O21 0.88 2.1 2.550(3) 110.8 . N21 H21 O24 0.88 2.14 2.621(2) 113.8 . O31C H31I O23 0.84 2.47 3.019(8) 124 1_565 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_publ_flag C117 N11 C11 C12 -20.9(4) y C117 N11 C11 C16 159.0(2) y N11 C11 C12 C13 177.8(2) y C16 C11 C12 C13 -2.1(3) y C11 C12 C13 C14 -0.2(4) y C12 C13 C14 C15 1.1(4) y C13 C14 C15 C16 0.4(4) y C17 O11 C16 C15 13.5(4) y C17 O11 C16 C11 -165.9(2) y C14 C15 C16 O11 178.0(2) y C14 C15 C16 C11 -2.7(4) y C12 C11 C16 O11 -177.0(2) y N11 C11 C16 O11 3.1(3) y C12 C11 C16 C15 3.6(3) y N11 C11 C16 C15 -176.3(2) y C16 O11 C17 C18 172.5(2) y O11 C17 C18 C113 -31.2(3) y O11 C17 C18 C19 149.0(2) y C113 C18 C19 C110 -0.4(4) y C17 C18 C19 C110 179.4(2) y C18 C19 C110 C111 2.4(4) y C18 C19 C110 O12 -178.9(2) y C127 O12 C110 C111 2.8(4) y C126 O12 C110 C111 -23.8(1) y C127 O12 C110 C19 -175.9(3) y C126 O12 C110 C19 157.6(1) y C19 C110 C111 C112 -1.1(4) y O12 C110 C111 C112 -179.7(2) y C110 C111 C112 C113 -2.1(4) y C110 C111 C112 C114 -179.9(2) y C111 C112 C113 C18 4.2(4) y C114 C112 C113 C18 -178.1(2) y C19 C18 C113 C112 -2.9(4) y C17 C18 C113 C112 177.3(2) y C113 C112 C114 C115 38.1(4) y C111 C112 C114 C115 -144.2(3) y C112 C114 C115 C116 5.8(4) y C118 O14 C116 C115 -147.61(19) y C114 C115 C116 O14 -98.3(3) y C11 N11 C117 O13 5.9(4) y C11 N11 C117 C118 -175.2(2) y C116 O14 C118 C119 107.6(2) y C116 O14 C118 C117 -128.69(19) y O13 C117 C118 O14 -143.7(2) y N11 C117 C118 O14 37.4(2) y O13 C117 C118 C119 -21.3(3) y N11 C117 C118 C119 159.79(19) y O14 C118 C119 C120 -63.0(2) y C117 C118 C119 C120 175.03(19) y C118 C119 C120 C121 179.8(2) y C119 C120 C121 C122 179.8(2) y C120 C121 C122 C123 -178.6(2) y C121 C122 C123 C124 -178.00(19) y C125 O16 C124 O15 -1.0(4) y C125 O16 C124 C123 179.6(2) y C122 C123 C124 O15 -0.2(4) y C122 C123 C124 O16 179.2(2) y C217 N21 C21 C22 5.1(4) y C217 N21 C21 C26 -177.7(2) y C26 C21 C22 C23 0.5(3) y N21 C21 C22 C23 177.6(2) y C21 C22 C23 C24 -0.9(4) y C22 C23 C24 C25 0.4(4) y C23 C24 C25 C26 0.5(4) y C27 O21 C26 C25 7.4(4) y C27 O21 C26 C21 -171.9(2) y C24 C25 C26 O21 179.8(2) y C24 C25 C26 C21 -0.9(4) y C22 C21 C26 O21 179.8(2) y N21 C21 C26 O21 2.4(3) y C22 C21 C26 C25 0.4(3) y N21 C21 C26 C25 -176.9(2) y C26 O21 C27 C28 176.2(2) y O21 C27 C28 C29 153.9(2) y O21 C27 C28 C213 -26.5(3) y C213 C28 C29 C210 -0.4(4) y C27 C28 C29 C210 179.2(2) y C226 O22 C210 C211 -5.7(4) y C226 O22 C210 C29 174.1(3) y C28 C29 C210 O22 -177.6(2) y C28 C29 C210 C211 2.2(4) y O22 C210 C211 C212 179.4(2) y C29 C210 C211 C212 -0.4(4) y C210 C211 C212 C213 -3.1(4) y C210 C211 C212 C214 179.3(2) y C29 C28 C213 C212 -3.2(4) y C27 C28 C213 C212 177.2(2) y C211 C212 C213 C28 4.9(4) y C214 C212 C213 C28 -177.5(2) y C211 C212 C214 C215 -143.6(3) y C213 C212 C214 C215 38.8(4) y C212 C214 C215 C216 5.4(4) y C218 O24 C216 C215 -146.8(2) y C214 C215 C216 O24 -100.1(3) y C21 N21 C217 O23 6.7(4) y C21 N21 C217 C218 -175.6(2) y C216 O24 C218 C219 116.9(2) y C216 O24 C218 C217 -121.3(2) y O23 C217 C218 O24 -168.1(2) y N21 C217 C218 O24 14.1(3) y O23 C217 C218 C219 -46.8(3) y N21 C217 C218 C219 135.4(2) y O24 C218 C219 C220 -65.0(2) y C217 C218 C219 C220 173.19(19) y C218 C219 C220 C221 176.6(2) y C219 C220 C221 C222 -178.1(2) y C220 C221 C222 C223 -178.4(2) y C221 C222 C223 C224 174.9(2) y C225 O26 C224 O25 -1.9(3) y C225 O26 C224 C223 178.9(2) y C222 C223 C224 O25 10.4(3) y C222 C223 C224 O26 -170.43(19) y _journal_paper_doi 10.1021/jm101092u