#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/51/72/1517237.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_1517237 loop_ _publ_author_name 'Logan, Angus W. J.' 'Sprague, Simon J.' 'Foster, Robert W.' 'Marx, L\'eo B' 'Garzya, Vincenzo' 'Hallside, Michal S.' 'Thompson, Amber L.' 'Burton, Jonathan W.' _publ_section_title ; Diastereoselective synthesis of fused lactone-pyrrolidinones; application to a formal synthesis of (-)-salinosporamide a. ; _journal_issue 16 _journal_name_full 'Organic letters' _journal_page_first 4078 _journal_page_last 4081 _journal_paper_doi 10.1021/ol501662t _journal_volume 16 _journal_year 2014 _chemical_absolute_configuration unk _chemical_formula_moiety 'C26 H35 N1 O6' _chemical_formula_sum 'C26 H35 N O6' _chemical_formula_weight 457.57 _chemical_melting_point ? _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary other _audit_creation_date 2012-09-24 _audit_creation_method CRYSTALS_ver_14.52 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.2769(1) _cell_length_b 19.0465(2) _cell_length_c 20.3494(4) _cell_measurement_reflns_used 14442 _cell_measurement_temperature 100 _cell_measurement_theta_max 32 _cell_measurement_theta_min 2 _cell_volume 2432.83(7) _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2009)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 28.5714 _diffrn_measured_fraction_theta_full 0.962 _diffrn_measured_fraction_theta_max 0.912 _diffrn_measurement_device Area _diffrn_measurement_device_type 'Rigaku Saturn724+' _diffrn_measurement_method dtprofit.ref _diffrn_radiation_monochromator Synchrotron _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.68890 _diffrn_reflns_av_R_equivalents 0.045 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 32517 _diffrn_reflns_theta_full 25.199 _diffrn_reflns_theta_max 31.898 _diffrn_reflns_theta_min 2.073 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_crystal_colour clear_pale_colourless _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 984 _exptl_crystal_size_max 0.050 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.33 _refine_diff_density_min -0.24 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9344 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 4704 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0383 _refine_ls_shift/su_max 0.0005171 _refine_ls_shift/su_mean 0.0000523 _refine_ls_structure_factor_coef Fsqd _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: 0.252E+04 0.418E+04 0.269E+04 0.120E+04 328. ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0999 _refine_ls_wR_factor_gt 0.0921 _refine_ls_wR_factor_ref 0.0999 _reflns_limit_h_max 9 _reflns_limit_h_min 0 _reflns_limit_k_max 29 _reflns_limit_k_min 0 _reflns_limit_l_max 27 _reflns_limit_l_min 0 _reflns_number_gt 4416 _reflns_number_total 4716 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 1.70 _oxford_diffrn_Wilson_scale 0.02 _oxford_refine_ls_r_factor_ref 0.0425 _oxford_refine_ls_scale 8.8(2) _oxford_reflns_number_all 4704 _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _oxford_structure_analysis_title DIA0174 _[local]_cod_data_source_file ol501662t_si_002.cif _[local]_cod_data_source_block 18 _[local]_cod_cif_authors_sg_H-M 'P 21 21 21 ' _[local]_cod_chemical_formula_sum_orig 'C26 H35 N1 O6' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value 'not measured' was changed to '?' - the value is undefined or not given. '_atom_sites_solution_primary' value 'Other' changed to 'other' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius Adding full bibliography for 1517236--1517237.cif. The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_database_code 1517237 #BEGIN Tags that were not found in dictionaries: _iucr_refine_instructions_details_constraints ; BLOCK SCALE X'S, U'S RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 6,X'S) H ( 61,X'S) H ( 62,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 143,X'S) H ( 142,X'S) RIDE C ( 16,X'S) H ( 162,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 192,X'S) H ( 191,X'S) RIDE C ( 24,X'S) H ( 241,X'S) H ( 243,X'S) H ( 242,X'S) RIDE C ( 25,X'S) H ( 252,X'S) H ( 251,X'S) H ( 253,X'S) RIDE C ( 26,X'S) H ( 262,X'S) H ( 263,X'S) H ( 261,X'S) RIDE C ( 31,X'S) H ( 313,X'S) H ( 311,X'S) H ( 312,X'S) RIDE C ( 32,X'S) H ( 321,X'S) H ( 323,X'S) H ( 322,X'S) RIDE C ( 33,X'S) H ( 332,X'S) H ( 331,X'S) H ( 333,X'S) END ; _iucr_refine_instructions_details_restraints ; NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; #END Tags that were not found in dictionaries loop_ _symmetry_equiv_pos_as_xyz x,y,z -x+1/2,-y,z+1/2 x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn N1 N 0.7471(2) 0.52363(6) 0.26791(6) 0.0204 1.0000 Uani . C2 C 0.7088(3) 0.49628(7) 0.20682(8) 0.0266 1.0000 Uani . C3 C 0.5869(3) 0.55036(7) 0.16846(8) 0.0260 1.0000 Uani . C4 C 0.4916(2) 0.59780(7) 0.22102(7) 0.0203 1.0000 Uani . C5 C 0.6517(2) 0.59288(6) 0.27852(7) 0.0175 1.0000 Uani . C6 C 0.9052(2) 0.49275(7) 0.31123(8) 0.0233 1.0000 Uani . C7 C 0.8124(3) 0.44295(7) 0.36164(8) 0.0221 1.0000 Uani . C8 C 0.9309(3) 0.42526(8) 0.41685(9) 0.0272 1.0000 Uani . C9 C 0.8541(3) 0.37858(8) 0.46381(9) 0.0290 1.0000 Uani . C10 C 0.6527(3) 0.34939(7) 0.45545(8) 0.0267 1.0000 Uani . C11 C 0.5325(3) 0.36618(8) 0.40038(9) 0.0302 1.0000 Uani . C12 C 0.6123(3) 0.41271(8) 0.35397(9) 0.0271 1.0000 Uani . O13 O 0.5601(3) 0.30336(7) 0.49842(6) 0.0351 1.0000 Uani . C14 C 0.6700(3) 0.28913(9) 0.55817(9) 0.0320 1.0000 Uani . O15 O 0.7755(3) 0.43954(6) 0.18789(7) 0.0380 1.0000 Uani . C16 C 0.4143(4) 0.52880(9) 0.12011(9) 0.0363 1.0000 Uani . C17 C 0.2974(3) 0.59243(10) 0.09800(9) 0.0322 1.0000 Uani . C18 C 0.3124(3) 0.65513(9) 0.12774(8) 0.0278 1.0000 Uani . C19 C 0.4389(2) 0.66825(7) 0.18997(7) 0.0219 1.0000 Uani . C20 C 0.5398(2) 0.59568(7) 0.34600(7) 0.0193 1.0000 Uani . O21 O 0.34953(18) 0.59168(7) 0.35303(6) 0.0287 1.0000 Uani . O22 O 0.68357(17) 0.60179(5) 0.39369(5) 0.0200 1.0000 Uani . C23 C 0.6187(3) 0.61009(8) 0.46340(7) 0.0225 1.0000 Uani . C24 C 0.4888(3) 0.67716(9) 0.47028(9) 0.0324 1.0000 Uani . C25 C 0.8327(3) 0.61695(10) 0.49788(9) 0.0326 1.0000 Uani . C26 C 0.4995(3) 0.54579(9) 0.48729(9) 0.0321 1.0000 Uani . C27 C 0.8210(2) 0.65075(6) 0.27320(7) 0.0180 1.0000 Uani . O28 O 0.98883(18) 0.64183(5) 0.24631(6) 0.0244 1.0000 Uani . O29 O 0.74627(17) 0.71041(5) 0.29863(5) 0.0198 1.0000 Uani . C30 C 0.8807(2) 0.77477(7) 0.29949(7) 0.0210 1.0000 Uani . C31 C 1.0784(3) 0.76131(8) 0.34055(8) 0.0256 1.0000 Uani . C32 C 0.7362(3) 0.82813(7) 0.33266(10) 0.0309 1.0000 Uani . C33 C 0.9334(3) 0.79750(8) 0.22985(8) 0.0273 1.0000 Uani . H31 H 0.6925 0.5782 0.1437 0.0310 1.0000 Uiso R H41 H 0.3598 0.5763 0.2360 0.0244 1.0000 Uiso R H61 H 0.9820 0.5299 0.3331 0.0284 1.0000 Uiso R H62 H 1.0050 0.4669 0.2837 0.0287 1.0000 Uiso R H81 H 1.0659 0.4454 0.4222 0.0333 1.0000 Uiso R H91 H 0.9363 0.3670 0.5013 0.0356 1.0000 Uiso R H111 H 0.3959 0.3457 0.3946 0.0363 1.0000 Uiso R H121 H 0.5285 0.4245 0.3164 0.0328 1.0000 Uiso R H141 H 0.5907 0.2514 0.5800 0.0476 1.0000 Uiso R H143 H 0.6718 0.3311 0.5852 0.0476 1.0000 Uiso R H142 H 0.8155 0.2736 0.5474 0.0476 1.0000 Uiso R H162 H 0.4719 0.5040 0.0831 0.0443 1.0000 Uiso R H161 H 0.3127 0.4959 0.1422 0.0447 1.0000 Uiso R H171 H 0.2099 0.5884 0.0586 0.0401 1.0000 Uiso R H181 H 0.2428 0.6942 0.1070 0.0336 1.0000 Uiso R H192 H 0.3580 0.6982 0.2209 0.0259 1.0000 Uiso R H191 H 0.5694 0.6934 0.1779 0.0256 1.0000 Uiso R H241 H 0.4610 0.6863 0.5160 0.0496 1.0000 Uiso R H243 H 0.5659 0.7160 0.4515 0.0486 1.0000 Uiso R H242 H 0.3554 0.6726 0.4482 0.0489 1.0000 Uiso R H252 H 0.8125 0.6208 0.5453 0.0485 1.0000 Uiso R H251 H 0.9047 0.6572 0.4815 0.0484 1.0000 Uiso R H253 H 0.9176 0.5769 0.4880 0.0480 1.0000 Uiso R H262 H 0.4825 0.5491 0.5346 0.0474 1.0000 Uiso R H263 H 0.5772 0.5042 0.4751 0.0478 1.0000 Uiso R H261 H 0.3597 0.5443 0.4673 0.0472 1.0000 Uiso R H313 H 1.1575 0.8047 0.3441 0.0382 1.0000 Uiso R H311 H 1.0378 0.7452 0.3837 0.0377 1.0000 Uiso R H312 H 1.1665 0.7259 0.3197 0.0374 1.0000 Uiso R H321 H 0.8109 0.8727 0.3352 0.0452 1.0000 Uiso R H323 H 0.6971 0.8128 0.3768 0.0447 1.0000 Uiso R H322 H 0.6078 0.8339 0.3067 0.0447 1.0000 Uiso R H332 H 1.0159 0.8409 0.2312 0.0421 1.0000 Uiso R H331 H 0.8070 0.8061 0.2066 0.0403 1.0000 Uiso R H333 H 1.0118 0.7623 0.2074 0.0396 1.0000 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 N1 0.0248(5) 0.0130(4) 0.0235(6) -0.0012(4) 0.0015(5) 0.0008(4) C2 0.0368(8) 0.0169(5) 0.0259(7) -0.0027(5) 0.0014(6) 0.0009(6) C3 0.0381(8) 0.0175(5) 0.0226(7) -0.0023(5) 0.0012(6) 0.0005(6) C4 0.0226(6) 0.0173(5) 0.0211(6) -0.0012(4) -0.0001(5) -0.0026(5) C5 0.0183(5) 0.0130(4) 0.0213(6) -0.0016(4) 0.0015(4) -0.0011(4) C6 0.0234(6) 0.0159(5) 0.0307(7) 0.0007(5) 0.0002(5) 0.0027(5) C7 0.0252(6) 0.0129(4) 0.0281(7) -0.0006(4) -0.0014(5) 0.0011(5) C8 0.0243(6) 0.0229(6) 0.0343(8) 0.0013(5) -0.0045(6) 0.0002(5) C9 0.0321(7) 0.0245(6) 0.0305(8) 0.0025(5) -0.0080(6) 0.0016(6) C10 0.0386(8) 0.0171(5) 0.0243(7) 0.0013(5) -0.0065(6) -0.0043(6) C11 0.0363(8) 0.0248(6) 0.0296(8) 0.0058(6) -0.0091(7) -0.0112(6) C12 0.0311(7) 0.0211(6) 0.0290(8) 0.0046(5) -0.0080(6) -0.0064(5) O13 0.0493(8) 0.0285(5) 0.0276(6) 0.0078(4) -0.0099(6) -0.0135(6) C14 0.0374(8) 0.0303(7) 0.0285(8) 0.0042(6) -0.0012(7) 0.0077(7) O15 0.0588(9) 0.0197(5) 0.0355(7) -0.0075(4) -0.0027(7) 0.0090(6) C16 0.0567(12) 0.0244(6) 0.0278(8) -0.0062(6) -0.0105(8) 0.0009(8) C17 0.0325(8) 0.0396(8) 0.0244(8) 0.0001(6) -0.0033(6) -0.0053(7) C18 0.0265(6) 0.0313(7) 0.0257(7) 0.0010(6) -0.0029(6) 0.0034(6) C19 0.0217(6) 0.0204(5) 0.0237(7) -0.0004(5) 0.0006(5) 0.0007(5) C20 0.0202(5) 0.0162(5) 0.0215(6) -0.0010(4) 0.0001(5) -0.0005(4) O21 0.0188(5) 0.0400(6) 0.0274(6) -0.0020(5) 0.0014(4) -0.0025(5) O22 0.0205(4) 0.0189(4) 0.0205(5) -0.0006(3) -0.0001(4) -0.0002(4) C23 0.0267(6) 0.0208(5) 0.0200(6) -0.0009(5) 0.0000(5) 0.0007(5) C24 0.0434(9) 0.0281(7) 0.0256(8) -0.0046(5) 0.0009(7) 0.0097(7) C25 0.0331(8) 0.0377(8) 0.0271(8) -0.0002(6) -0.0078(7) -0.0011(7) C26 0.0395(9) 0.0288(7) 0.0282(8) 0.0027(6) 0.0081(7) -0.0056(7) C27 0.0190(5) 0.0129(4) 0.0222(6) -0.0005(4) -0.0011(5) -0.0012(4) O28 0.0207(4) 0.0187(4) 0.0338(6) -0.0020(4) 0.0057(4) -0.0007(4) O29 0.0205(4) 0.0121(3) 0.0267(5) -0.0018(3) 0.0016(4) -0.0001(3) C30 0.0256(6) 0.0129(4) 0.0244(7) -0.0010(4) -0.0009(5) -0.0016(4) C31 0.0270(6) 0.0235(6) 0.0262(7) -0.0019(5) -0.0064(6) -0.0034(5) C32 0.0359(8) 0.0161(5) 0.0407(9) -0.0064(5) 0.0032(7) 0.0025(6) C33 0.0373(8) 0.0188(5) 0.0257(7) 0.0049(5) -0.0016(6) -0.0040(6) 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 0.0020 0.0020 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 0.0070 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 0.0040 0.0030 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' 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 C2 N1 C5 113.87(12) yes C2 N1 C6 121.16(12) yes C5 N1 C6 123.69(12) yes N1 C2 C3 107.48(12) yes N1 C2 O15 124.25(16) yes C3 C2 O15 128.14(15) yes C2 C3 C4 104.02(13) yes C2 C3 C16 120.94(13) yes C4 C3 C16 109.56(15) yes C2 C3 H31 106.9 no C4 C3 H31 107.7 no C16 C3 H31 107.1 no C3 C4 C5 103.89(12) yes C3 C4 C19 108.52(12) yes C5 C4 C19 120.66(11) yes C3 C4 H41 107.7 no C5 C4 H41 106.9 no C19 C4 H41 108.5 no C4 C5 N1 102.06(10) yes C4 C5 C20 112.07(11) yes N1 C5 C20 110.39(11) yes C4 C5 C27 110.69(11) yes N1 C5 C27 110.70(11) yes C20 C5 C27 110.66(10) yes N1 C6 C7 113.73(13) yes N1 C6 H61 109.0 no C7 C6 H61 109.8 no N1 C6 H62 107.1 no C7 C6 H62 108.7 no H61 C6 H62 108.3 no C6 C7 C8 119.61(14) yes C6 C7 C12 122.07(14) yes C8 C7 C12 118.30(14) yes C7 C8 C9 121.66(15) yes C7 C8 H81 118.6 no C9 C8 H81 119.7 no C8 C9 C10 119.09(15) yes C8 C9 H91 120.8 no C10 C9 H91 120.1 no C9 C10 C11 120.02(15) yes C9 C10 O13 124.33(15) yes C11 C10 O13 115.65(15) yes C10 C11 C12 120.00(16) yes C10 C11 H111 119.7 no C12 C11 H111 120.3 no C7 C12 C11 120.92(15) yes C7 C12 H121 119.4 no C11 C12 H121 119.7 no C10 O13 C14 117.52(15) yes O13 C14 H141 106.3 no O13 C14 H143 109.5 no H141 C14 H143 110.7 no O13 C14 H142 108.5 no H141 C14 H142 110.5 no H143 C14 H142 111.3 no C3 C16 C17 109.12(13) yes C3 C16 H162 111.9 no C17 C16 H162 110.4 no C3 C16 H161 109.5 no C17 C16 H161 109.4 no H162 C16 H161 106.5 no C16 C17 C18 123.66(16) yes C16 C17 H171 117.6 no C18 C17 H171 118.7 no C17 C18 C19 124.08(15) yes C17 C18 H181 117.3 no C19 C18 H181 118.6 no C4 C19 C18 108.41(12) yes C4 C19 H192 110.9 no C18 C19 H192 110.9 no C4 C19 H191 110.7 no C18 C19 H191 108.1 no H192 C19 H191 107.8 no C5 C20 O21 123.66(14) yes C5 C20 O22 110.09(11) yes O21 C20 O22 126.24(14) yes C20 O22 C23 121.35(12) yes O22 C23 C24 108.93(12) yes O22 C23 C25 101.99(12) yes C24 C23 C25 111.00(14) yes O22 C23 C26 110.86(12) yes C24 C23 C26 112.62(14) yes C25 C23 C26 110.94(14) yes C23 C24 H241 109.7 no C23 C24 H243 109.8 no H241 C24 H243 109.6 no C23 C24 H242 110.5 no H241 C24 H242 108.2 no H243 C24 H242 108.9 no C23 C25 H252 110.4 no C23 C25 H251 109.1 no H252 C25 H251 110.4 no C23 C25 H253 109.2 no H252 C25 H253 110.0 no H251 C25 H253 107.8 no C23 C26 H262 108.6 no C23 C26 H263 109.4 no H262 C26 H263 111.4 no C23 C26 H261 109.7 no H262 C26 H261 108.6 no H263 C26 H261 109.1 no C5 C27 O28 122.59(11) yes C5 C27 O29 109.95(11) yes O28 C27 O29 127.34(12) yes C27 O29 C30 120.47(11) yes O29 C30 C31 109.32(11) yes O29 C30 C32 102.57(12) yes C31 C30 C32 110.87(13) yes O29 C30 C33 110.34(11) yes C31 C30 C33 112.56(13) yes C32 C30 C33 110.73(13) yes C30 C31 H313 108.4 no C30 C31 H311 109.8 no H313 C31 H311 109.8 no C30 C31 H312 110.1 no H313 C31 H312 109.5 no H311 C31 H312 109.1 no C30 C32 H321 108.7 no C30 C32 H323 111.0 no H321 C32 H323 109.4 no C30 C32 H322 109.2 no H321 C32 H322 109.4 no H323 C32 H322 109.0 no C30 C33 H332 109.3 no C30 C33 H331 109.6 no H332 C33 H331 108.4 no C30 C33 H333 111.2 no H332 C33 H333 109.7 no H331 C33 H333 108.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 1.369(2) yes N1 C5 1.4646(16) yes N1 C6 1.452(2) yes C2 C3 1.502(2) yes C2 O15 1.2213(18) yes C3 C4 1.523(2) yes C3 C16 1.520(3) yes C3 H31 0.986 no C4 C5 1.545(2) yes C4 C19 1.5194(19) yes C4 H41 0.972 no C5 C20 1.5434(19) yes C5 C27 1.5348(18) yes C6 C7 1.514(2) yes C6 H61 0.964 no C6 H62 0.974 no C7 C8 1.389(2) yes C7 C12 1.391(2) yes C8 C9 1.392(2) yes C8 H81 0.936 no C9 C10 1.392(2) yes C9 H91 0.947 no C10 C11 1.388(2) yes C10 O13 1.3677(19) yes C11 C12 1.389(2) yes C11 H111 0.949 no C12 H121 0.954 no O13 C14 1.424(2) yes C14 H141 0.981 no C14 H143 0.971 no C14 H142 0.985 no C16 C17 1.487(3) yes C16 H162 0.959 no C16 H161 1.000 no C17 C18 1.342(2) yes C17 H171 0.974 no C18 C19 1.515(2) yes C18 H181 0.961 no C19 H192 0.989 no C19 H191 0.981 no C20 O21 1.2053(17) yes C20 O22 1.3302(17) yes O22 C23 1.4843(18) yes C23 C24 1.522(2) yes C23 C25 1.521(2) yes C23 C26 1.515(2) yes C24 H241 0.963 no C24 H243 0.964 no C24 H242 0.955 no C25 H252 0.976 no C25 H251 0.951 no C25 H253 0.952 no C26 H262 0.970 no C26 H263 0.964 no C26 H261 0.967 no C27 O28 1.1995(17) yes C27 O29 1.3337(15) yes O29 C30 1.4883(16) yes C30 C31 1.518(2) yes C30 C32 1.520(2) yes C30 C33 1.518(2) yes C31 H313 0.967 no C31 H311 0.965 no C31 H312 0.970 no C32 H321 0.971 no C32 H323 0.975 no C32 H322 0.970 no C33 H332 0.976 no C33 H331 0.939 no C33 H333 0.949 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_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 C14 H142 O13 3_556 153.33 0.985 2.319 3.229(2) yes