#------------------------------------------------------------------------------ #$Date: 2013-12-28 07:07:06 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/77/1507719.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_1507719 loop_ _publ_author_name 'Ma, Zhi-Xiong' 'Feltenberger, John B.' 'Hsung, Richard P.' _publ_section_title ; Total Syntheses of Chelidonine and Norchelidonine via an Enamide-Benzyne-[2 + 2] Cycloaddition Cascade. ; _journal_issue 11 _journal_name_full 'Organic letters' _journal_page_first 2742 _journal_page_last 2745 _journal_volume 14 _journal_year 2012 _chemical_formula_moiety 'C27 H21 N O6' _chemical_formula_sum 'C27 H21 N O6' _chemical_formula_weight 455.45 _chemical_name_systematic ; ? ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.696(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 42.39(2) _cell_length_b 13.376(6) _cell_length_c 7.320(3) _cell_measurement_reflns_used 1017 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 23.36 _cell_measurement_theta_min 2.84 _cell_volume 4150(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 123(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.0927 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_h_min -50 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3783 _diffrn_reflns_theta_full 25.09 _diffrn_reflns_theta_max 25.09 _diffrn_reflns_theta_min 2.10 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.861954 _exptl_absorpt_correction_T_min 0.668942 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'TWINABS 2008/4' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1904 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.276 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 308 _refine_ls_number_reflns 3783 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.018 _refine_ls_R_factor_all 0.1147 _refine_ls_R_factor_gt 0.0588 _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^)+(0.0554P)^2^+0.9292P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1176 _refine_ls_wR_factor_ref 0.1443 _reflns_number_gt 2314 _reflns_number_total 3783 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL 12079t in C2/c CELL 0.71073 42.3938 13.3761 7.3199 90.000 90.696 90.000 ZERR 8.00 0.0211 0.0060 0.0034 0.000 0.012 0.000 LATT 7 SYMM -x, y, -z+1/2 SFAC C H N O UNIT 216 168 8 48 TEMP -150.000 ACTA L.S. 8 FMAP 2 PLAN 20 BOND $H htab list 4 conf Merg 0 omit 1 1 0 WGHT 0.055400 0.929200 BASF 0.38727 FVAR 0.21263 O1 4 0.040986 0.157098 0.629807 11.00000 0.03250 0.04543 = 0.04358 -0.00785 0.00547 -0.01248 O2 4 0.027120 0.072225 0.366807 11.00000 0.03182 0.04740 = 0.06305 -0.01334 -0.00078 -0.01236 O3 4 0.291373 0.114178 0.693543 11.00000 0.03079 0.03295 = 0.02704 0.00175 -0.00313 0.00164 O4 4 0.246677 0.150802 0.862853 11.00000 0.02917 0.03180 = 0.02438 0.00198 -0.00476 0.00150 O5 4 0.165196 0.362724 0.819915 11.00000 0.02945 0.03168 = 0.02400 -0.00681 -0.00501 0.00381 O6 4 0.137123 0.390848 0.558167 11.00000 0.03089 0.02347 = 0.02280 -0.00456 -0.00378 0.00480 N1 3 0.161192 0.243754 0.599479 11.00000 0.02629 0.02412 = 0.02166 -0.00539 -0.00543 0.00350 C1 1 0.151581 0.214120 0.413721 11.00000 0.02906 0.02478 = 0.02171 -0.00448 -0.00398 -0.00077 AFIX 13 H1A 2 0.151531 0.276460 0.338312 11.00000 -1.20000 AFIX 0 C2 1 0.118358 0.171920 0.402585 11.00000 0.02896 0.01665 = 0.02540 0.00230 -0.00365 0.00252 C3 1 0.096526 0.187556 0.542682 11.00000 0.03122 0.02319 = 0.02803 -0.00206 -0.00208 -0.00156 AFIX 43 H3A 2 0.102362 0.220174 0.653312 11.00000 -1.20000 AFIX 0 C4 1 0.066476 0.153616 0.512314 11.00000 0.03013 0.02427 = 0.03163 0.00052 0.00427 -0.00064 C5 1 0.014694 0.131425 0.513101 11.00000 0.03367 0.05292 = 0.06246 -0.01475 0.00231 -0.00929 AFIX 23 H5A 2 -0.001157 0.092805 0.581874 11.00000 -1.20000 H5B 2 0.004511 0.192605 0.464267 11.00000 -1.20000 AFIX 0 C6 1 0.058211 0.103636 0.355238 11.00000 0.02895 0.02320 = 0.04585 0.00149 -0.00604 -0.00655 C7 1 0.079099 0.085953 0.216991 11.00000 0.03436 0.02500 = 0.03193 -0.00272 -0.00921 -0.00243 AFIX 43 H7A 2 0.072939 0.051232 0.109107 11.00000 -1.20000 AFIX 0 C8 1 0.109793 0.121381 0.242439 11.00000 0.03276 0.01893 = 0.02292 0.00137 -0.00888 0.00185 C9 1 0.133986 0.107350 0.094367 11.00000 0.03924 0.02909 = 0.02523 -0.00800 -0.00355 -0.00224 AFIX 23 H9A 2 0.128691 0.046948 0.022101 11.00000 -1.20000 H9B 2 0.133432 0.165618 0.010995 11.00000 -1.20000 AFIX 0 C10 1 0.166424 0.096586 0.174651 11.00000 0.03361 0.01830 = 0.02650 -0.00142 -0.00036 0.00153 AFIX 43 H10A 2 0.181133 0.054801 0.114387 11.00000 -1.20000 AFIX 0 C11 1 0.175496 0.143068 0.326749 11.00000 0.02950 0.01926 = 0.02327 -0.00127 -0.00158 0.00017 C12 1 0.207094 0.133024 0.411266 11.00000 0.02883 0.01494 = 0.02243 -0.00180 -0.00137 0.00164 C13 1 0.233929 0.110244 0.311684 11.00000 0.03074 0.01817 = 0.02057 -0.00023 0.00136 0.00014 AFIX 43 H13A 2 0.231962 0.100109 0.183597 11.00000 -1.20000 AFIX 0 C14 1 0.263538 0.101891 0.394273 11.00000 0.03004 0.01783 = 0.02749 -0.00172 0.00492 0.00079 AFIX 43 H14A 2 0.281775 0.086266 0.325740 11.00000 -1.20000 AFIX 0 C15 1 0.265135 0.117282 0.579217 11.00000 0.02099 0.01873 = 0.02676 0.00281 -0.00422 -0.00015 C16 1 0.280638 0.147680 0.868602 11.00000 0.03236 0.02771 = 0.02961 0.00094 -0.00552 0.00067 AFIX 23 H16A 2 0.289201 0.214988 0.895764 11.00000 -1.20000 H16B 2 0.287954 0.101227 0.965509 11.00000 -1.20000 AFIX 0 C17 1 0.238710 0.139463 0.679708 11.00000 0.03415 0.01581 = 0.01939 -0.00051 -0.00122 -0.00184 C18 1 0.209384 0.148009 0.602380 11.00000 0.02699 0.01478 = 0.02238 0.00028 -0.00223 -0.00137 C19 1 0.180075 0.172415 0.706163 11.00000 0.03028 0.02166 = 0.02107 0.00012 -0.00174 -0.00029 AFIX 23 H19A 2 0.167745 0.110746 0.727524 11.00000 -1.20000 H19B 2 0.185785 0.201790 0.826219 11.00000 -1.20000 AFIX 0 C20 1 0.155545 0.334892 0.671572 11.00000 0.02319 0.02308 = 0.02428 -0.00296 0.00244 0.00134 C21 1 0.130791 0.491985 0.620373 11.00000 0.03761 0.02041 = 0.02438 -0.00319 0.00028 0.00140 AFIX 23 H21A 2 0.147248 0.537864 0.574839 11.00000 -1.20000 H21B 2 0.131281 0.494088 0.755571 11.00000 -1.20000 AFIX 0 C22 1 0.098953 0.524947 0.550874 11.00000 0.03295 0.02416 = 0.01790 -0.00049 0.00352 0.00313 C23 1 0.075201 0.459488 0.498354 11.00000 0.03502 0.03052 = 0.02731 -0.00020 0.00315 0.00186 AFIX 43 H23A 2 0.078891 0.389446 0.500924 11.00000 -1.20000 AFIX 0 C24 1 0.046017 0.496015 0.441971 11.00000 0.03216 0.04702 = 0.03406 -0.00070 -0.00232 -0.00183 AFIX 43 H24A 2 0.029939 0.450631 0.404839 11.00000 -1.20000 AFIX 0 C25 1 0.040114 0.596814 0.439224 11.00000 0.03407 0.04664 = 0.04132 -0.00180 0.00093 0.01345 AFIX 43 H25A 2 0.020017 0.621046 0.401254 11.00000 -1.20000 AFIX 0 C26 1 0.063484 0.662764 0.491820 11.00000 0.05086 0.03436 = 0.04347 -0.00011 -0.00107 0.01530 AFIX 43 H26A 2 0.059468 0.732636 0.490779 11.00000 -1.20000 AFIX 0 C27 1 0.092813 0.627309 0.546186 11.00000 0.04071 0.02964 = 0.03666 -0.00193 -0.00190 0.00209 AFIX 43 H27A 2 0.108916 0.673211 0.580647 11.00000 -1.20000 HKLF 5 REM 12079t in C2/c REM R1 = 0.0588 for 2314 Fo > 4sig(Fo) and 0.1147 for all 3783 data REM 308 parameters refined using 0 restraints END WGHT 0.0554 0.9283 REM Highest difference peak 0.276, deepest hole -0.295, 1-sigma level 0.067 Q1 1 0.1898 0.2188 0.9731 11.00000 0.05 0.28 Q2 1 0.2098 0.1542 0.9971 11.00000 0.05 0.26 Q3 1 0.0488 0.2036 0.3831 11.00000 0.05 0.25 Q4 1 0.1321 0.0504 -0.0837 11.00000 0.05 0.25 Q5 1 0.0000 0.5615 0.2500 10.50000 0.05 0.22 Q6 1 0.0118 0.4012 0.3311 11.00000 0.05 0.22 Q7 1 0.1889 0.3178 0.4970 11.00000 0.05 0.22 Q8 1 0.2082 0.0331 -0.0394 11.00000 0.05 0.22 Q9 1 0.1103 -0.0218 -0.1187 11.00000 0.05 0.21 Q10 1 0.1698 0.2007 0.0348 11.00000 0.05 0.21 Q11 1 0.0708 0.7394 0.4306 11.00000 0.05 0.21 Q12 1 0.1287 0.0765 0.7355 11.00000 0.05 0.20 Q13 1 0.1621 0.3977 0.3504 11.00000 0.05 0.20 Q14 1 0.2097 0.1595 0.5045 11.00000 0.05 0.20 Q15 1 0.1196 0.2447 -0.0549 11.00000 0.05 0.20 Q16 1 0.1818 0.0194 0.0774 11.00000 0.05 0.19 Q17 1 0.0506 0.5543 0.2195 11.00000 0.05 0.19 Q18 1 0.0492 0.6410 0.2809 11.00000 0.05 0.19 Q19 1 0.0000 0.0563 0.7500 10.50000 0.05 0.19 Q20 1 0.0107 0.1964 0.3103 11.00000 0.05 0.19 ; _[local]_cod_data_source_file ol300967a_si_003.cif _[local]_cod_data_source_block 12079t5 _[local]_cod_cif_authors_sg_H-M C2/c _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 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 4151(3) _cod_database_code 1507719 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags O1 O 0.04099(5) 0.15710(18) 0.6298(3) 0.0405(7) Uani 1 1 d . O2 O 0.02712(5) 0.07223(19) 0.3668(4) 0.0474(7) Uani 1 1 d . O3 O 0.29137(5) 0.11418(16) 0.6935(3) 0.0303(6) Uani 1 1 d . O4 O 0.24668(5) 0.15080(15) 0.8629(3) 0.0285(5) Uani 1 1 d . O5 O 0.16520(5) 0.36272(16) 0.8199(3) 0.0284(5) Uani 1 1 d . O6 O 0.13712(5) 0.39085(15) 0.5582(3) 0.0258(5) Uani 1 1 d . N1 N 0.16119(5) 0.24375(19) 0.5995(3) 0.0241(6) Uani 1 1 d . C1 C 0.15158(7) 0.2141(2) 0.4137(4) 0.0252(8) Uani 1 1 d . H1A H 0.1515 0.2765 0.3383 0.030 Uiso 1 1 calc R C2 C 0.11836(7) 0.1719(2) 0.4026(4) 0.0237(7) Uani 1 1 d . C3 C 0.09653(7) 0.1876(2) 0.5427(5) 0.0275(8) Uani 1 1 d . H3A H 0.1024 0.2202 0.6533 0.033 Uiso 1 1 calc R C4 C 0.06648(7) 0.1536(2) 0.5123(5) 0.0286(8) Uani 1 1 d . C5 C 0.01469(8) 0.1314(3) 0.5131(6) 0.0497(11) Uani 1 1 d . H5A H -0.0012 0.0928 0.5819 0.060 Uiso 1 1 calc R H5B H 0.0045 0.1926 0.4643 0.060 Uiso 1 1 calc R C6 C 0.05821(7) 0.1036(2) 0.3552(5) 0.0327(9) Uani 1 1 d . C7 C 0.07910(7) 0.0860(2) 0.2170(5) 0.0305(8) Uani 1 1 d . H7A H 0.0729 0.0512 0.1091 0.037 Uiso 1 1 calc R C8 C 0.10979(7) 0.1214(2) 0.2424(4) 0.0249(7) Uani 1 1 d . C9 C 0.13399(7) 0.1074(3) 0.0944(4) 0.0312(8) Uani 1 1 d . H9A H 0.1287 0.0469 0.0221 0.037 Uiso 1 1 calc R H9B H 0.1334 0.1656 0.0110 0.037 Uiso 1 1 calc R C10 C 0.16642(7) 0.0966(2) 0.1747(4) 0.0261(8) Uani 1 1 d . H10A H 0.1811 0.0548 0.1144 0.031 Uiso 1 1 calc R C11 C 0.17550(7) 0.1431(2) 0.3267(4) 0.0240(7) Uani 1 1 d . C12 C 0.20709(7) 0.1330(2) 0.4113(4) 0.0221(7) Uani 1 1 d . C13 C 0.23393(7) 0.1102(2) 0.3117(4) 0.0232(7) Uani 1 1 d . H13A H 0.2320 0.1001 0.1836 0.028 Uiso 1 1 calc R C14 C 0.26354(7) 0.1019(2) 0.3943(4) 0.0251(8) Uani 1 1 d . H14A H 0.2818 0.0863 0.3257 0.030 Uiso 1 1 calc R C15 C 0.26514(7) 0.1173(2) 0.5792(4) 0.0222(7) Uani 1 1 d . C16 C 0.28064(7) 0.1477(2) 0.8686(4) 0.0299(8) Uani 1 1 d . H16A H 0.2892 0.2150 0.8958 0.036 Uiso 1 1 calc R H16B H 0.2880 0.1012 0.9655 0.036 Uiso 1 1 calc R C17 C 0.23871(7) 0.1395(2) 0.6797(4) 0.0231(7) Uani 1 1 d . C18 C 0.20938(7) 0.1480(2) 0.6024(4) 0.0214(7) Uani 1 1 d . C19 C 0.18008(7) 0.1724(2) 0.7062(4) 0.0244(7) Uani 1 1 d . H19A H 0.1677 0.1107 0.7275 0.029 Uiso 1 1 calc R H19B H 0.1858 0.2018 0.8262 0.029 Uiso 1 1 calc R C20 C 0.15554(7) 0.3349(2) 0.6716(4) 0.0235(7) Uani 1 1 d . C21 C 0.13079(7) 0.4920(2) 0.6204(4) 0.0275(8) Uani 1 1 d . H21A H 0.1472 0.5379 0.5748 0.033 Uiso 1 1 calc R H21B H 0.1313 0.4941 0.7556 0.033 Uiso 1 1 calc R C22 C 0.09895(7) 0.5249(2) 0.5509(4) 0.0250(8) Uani 1 1 d . C23 C 0.07520(7) 0.4595(3) 0.4984(4) 0.0309(8) Uani 1 1 d . H23A H 0.0789 0.3894 0.5009 0.037 Uiso 1 1 calc R C24 C 0.04602(8) 0.4960(3) 0.4420(5) 0.0378(9) Uani 1 1 d . H24A H 0.0299 0.4506 0.4048 0.045 Uiso 1 1 calc R C25 C 0.04011(8) 0.5968(3) 0.4392(5) 0.0407(9) Uani 1 1 d . H25A H 0.0200 0.6210 0.4013 0.049 Uiso 1 1 calc R C26 C 0.06348(9) 0.6628(3) 0.4918(5) 0.0429(10) Uani 1 1 d . H26A H 0.0595 0.7326 0.4908 0.051 Uiso 1 1 calc R C27 C 0.09281(8) 0.6273(3) 0.5462(5) 0.0357(9) Uani 1 1 d . H27A H 0.1089 0.6732 0.5806 0.043 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 0.0325(13) 0.0454(16) 0.0436(16) -0.0079(13) 0.0055(12) -0.0125(11) O2 0.0318(13) 0.0474(17) 0.0630(19) -0.0133(14) -0.0008(13) -0.0124(11) O3 0.0308(12) 0.0329(13) 0.0270(13) 0.0017(11) -0.0031(10) 0.0016(10) O4 0.0292(12) 0.0318(13) 0.0244(13) 0.0020(11) -0.0048(10) 0.0015(10) O5 0.0294(12) 0.0317(13) 0.0240(13) -0.0068(11) -0.0050(10) 0.0038(10) O6 0.0309(12) 0.0235(12) 0.0228(12) -0.0046(10) -0.0038(10) 0.0048(9) N1 0.0263(14) 0.0241(15) 0.0217(15) -0.0054(12) -0.0054(12) 0.0035(11) C1 0.0291(17) 0.0248(19) 0.0217(18) -0.0045(15) -0.0040(14) -0.0008(13) C2 0.0290(17) 0.0166(17) 0.0254(18) 0.0023(15) -0.0037(14) 0.0025(13) C3 0.0312(18) 0.0232(19) 0.0280(19) -0.0021(16) -0.0021(15) -0.0016(14) C4 0.0301(18) 0.0243(19) 0.032(2) 0.0005(16) 0.0043(15) -0.0006(14) C5 0.034(2) 0.053(3) 0.062(3) -0.015(2) 0.002(2) -0.0093(18) C6 0.0289(19) 0.0232(19) 0.046(2) 0.0015(18) -0.0060(16) -0.0066(14) C7 0.0344(19) 0.025(2) 0.032(2) -0.0027(16) -0.0092(16) -0.0024(14) C8 0.0328(18) 0.0189(18) 0.0229(18) 0.0014(15) -0.0089(14) 0.0019(13) C9 0.039(2) 0.029(2) 0.0252(19) -0.0080(16) -0.0035(15) -0.0022(15) C10 0.0336(18) 0.0183(17) 0.0265(19) -0.0014(15) -0.0004(15) 0.0015(13) C11 0.0295(17) 0.0193(17) 0.0233(18) -0.0013(15) -0.0016(14) 0.0002(13) C12 0.0288(17) 0.0149(17) 0.0224(17) -0.0018(14) -0.0014(14) 0.0016(13) C13 0.0307(18) 0.0182(17) 0.0206(17) -0.0002(14) 0.0014(14) 0.0001(13) C14 0.0300(18) 0.0178(17) 0.027(2) -0.0017(15) 0.0049(15) 0.0008(13) C15 0.0210(16) 0.0187(17) 0.0268(18) 0.0028(14) -0.0042(14) -0.0002(12) C16 0.0324(19) 0.0277(19) 0.0296(19) 0.0009(16) -0.0055(15) 0.0007(14) C17 0.0341(18) 0.0158(17) 0.0194(17) -0.0005(14) -0.0012(14) -0.0018(13) C18 0.0270(17) 0.0148(16) 0.0224(18) 0.0003(14) -0.0022(14) -0.0014(12) C19 0.0303(17) 0.0217(18) 0.0211(17) 0.0001(14) -0.0017(14) -0.0003(13) C20 0.0232(17) 0.0231(19) 0.0243(19) -0.0030(16) 0.0024(14) 0.0013(13) C21 0.0376(19) 0.0204(18) 0.0244(19) -0.0032(15) 0.0003(15) 0.0014(14) C22 0.0330(18) 0.0242(19) 0.0179(17) -0.0005(15) 0.0035(14) 0.0031(14) C23 0.0350(19) 0.031(2) 0.027(2) -0.0002(16) 0.0031(15) 0.0019(15) C24 0.032(2) 0.047(3) 0.034(2) -0.0007(19) -0.0023(16) -0.0018(17) C25 0.034(2) 0.047(3) 0.041(2) -0.002(2) 0.0009(17) 0.0135(18) C26 0.051(2) 0.034(2) 0.043(2) -0.0001(19) -0.0011(19) 0.0153(18) C27 0.041(2) 0.030(2) 0.037(2) -0.0019(17) -0.0019(17) 0.0021(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C4 O1 C5 103.1(3) C6 O2 C5 103.6(3) C15 O3 C16 105.6(2) C17 O4 C16 104.9(2) C20 O6 C21 115.4(2) C20 N1 C19 118.5(3) C20 N1 C1 123.8(3) C19 N1 C1 117.5(2) N1 C1 C2 113.4(2) N1 C1 C11 112.0(2) C2 C1 C11 111.4(2) N1 C1 H1A 106.5 C2 C1 H1A 106.5 C11 C1 H1A 106.5 C8 C2 C3 121.2(3) C8 C2 C1 117.1(3) C3 C2 C1 121.6(3) C4 C3 C2 116.9(3) C4 C3 H3A 121.6 C2 C3 H3A 121.6 C3 C4 C6 121.7(3) C3 C4 O1 128.2(3) C6 C4 O1 110.0(3) O2 C5 O1 106.6(3) O2 C5 H5A 110.4 O1 C5 H5A 110.4 O2 C5 H5B 110.4 O1 C5 H5B 110.4 H5A C5 H5B 108.6 C4 C6 C7 122.8(3) C4 C6 O2 109.3(3) C7 C6 O2 127.9(3) C6 C7 C8 116.9(3) C6 C7 H7A 121.6 C8 C7 H7A 121.6 C7 C8 C2 120.6(3) C7 C8 C9 120.1(3) C2 C8 C9 119.3(3) C10 C9 C8 111.0(3) C10 C9 H9A 109.4 C8 C9 H9A 109.4 C10 C9 H9B 109.4 C8 C9 H9B 109.4 H9A C9 H9B 108.0 C11 C10 C9 122.7(3) C11 C10 H10A 118.7 C9 C10 H10A 118.7 C10 C11 C12 124.1(3) C10 C11 C1 116.9(3) C12 C11 C1 118.9(3) C13 C12 C18 120.1(3) C13 C12 C11 123.0(3) C18 C12 C11 116.9(3) C14 C13 C12 121.9(3) C14 C13 H13A 119.0 C12 C13 H13A 119.0 C15 C14 C13 116.8(3) C15 C14 H14A 121.6 C13 C14 H14A 121.6 C14 C15 C17 121.9(3) C14 C15 O3 128.5(3) C17 C15 O3 109.6(3) O3 C16 O4 108.1(2) O3 C16 H16A 110.1 O4 C16 H16A 110.1 O3 C16 H16B 110.1 O4 C16 H16B 110.1 H16A C16 H16B 108.4 C18 C17 C15 122.6(3) C18 C17 O4 127.0(3) C15 C17 O4 110.4(3) C17 C18 C12 116.7(3) C17 C18 C19 124.3(3) C12 C18 C19 118.9(3) N1 C19 C18 108.8(2) N1 C19 H19A 109.9 C18 C19 H19A 109.9 N1 C19 H19B 109.9 C18 C19 H19B 109.9 H19A C19 H19B 108.3 O5 C20 N1 124.5(3) O5 C20 O6 124.2(3) N1 C20 O6 111.2(3) O6 C21 C22 109.6(2) O6 C21 H21A 109.7 C22 C21 H21A 109.7 O6 C21 H21B 109.7 C22 C21 H21B 109.7 H21A C21 H21B 108.2 C23 C22 C27 118.6(3) C23 C22 C21 123.7(3) C27 C22 C21 117.6(3) C22 C23 C24 120.1(3) C22 C23 H23A 119.9 C24 C23 H23A 119.9 C25 C24 C23 120.8(3) C25 C24 H24A 119.6 C23 C24 H24A 119.6 C24 C25 C26 119.7(3) C24 C25 H25A 120.2 C26 C25 H25A 120.2 C25 C26 C27 120.1(4) C25 C26 H26A 120.0 C27 C26 H26A 120.0 C26 C27 C22 120.7(3) C26 C27 H27A 119.7 C22 C27 H27A 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C4 1.390(4) O1 C5 1.438(4) O2 C6 1.387(4) O2 C5 1.437(4) O3 C15 1.384(4) O3 C16 1.437(4) O4 C17 1.387(4) O4 C16 1.440(4) O5 C20 1.214(4) O6 C20 1.358(4) O6 C21 1.453(4) N1 C20 1.351(4) N1 C19 1.465(4) N1 C1 1.469(4) C1 C2 1.519(4) C1 C11 1.534(4) C1 H1A 1.0000 C2 C8 1.397(4) C2 C3 1.405(4) C3 C4 1.368(4) C3 H3A 0.9500 C4 C6 1.372(5) C5 H5A 0.9900 C5 H5B 0.9900 C6 C7 1.373(5) C7 C8 1.395(4) C7 H7A 0.9500 C8 C9 1.513(4) C9 C10 1.496(4) C9 H9A 0.9900 C9 H9B 0.9900 C10 C11 1.328(4) C10 H10A 0.9500 C11 C12 1.475(4) C12 C13 1.392(4) C12 C18 1.415(4) C13 C14 1.391(4) C13 H13A 0.9500 C14 C15 1.370(4) C14 H14A 0.9500 C15 C17 1.380(4) C16 H16A 0.9900 C16 H16B 0.9900 C17 C18 1.365(4) C18 C19 1.500(4) C19 H19A 0.9900 C19 H19B 0.9900 C21 C22 1.503(4) C21 H21A 0.9900 C21 H21B 0.9900 C22 C23 1.385(4) C22 C27 1.394(4) C23 C24 1.388(4) C23 H23A 0.9500 C24 C25 1.371(5) C24 H24A 0.9500 C25 C26 1.378(5) C25 H25A 0.9500 C26 C27 1.385(5) C26 H26A 0.9500 C27 H27A 0.9500 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 C20 N1 C1 C2 -87.5(3) C19 N1 C1 C2 97.3(3) C20 N1 C1 C11 145.4(3) C19 N1 C1 C11 -29.7(3) N1 C1 C2 C8 -165.9(3) C11 C1 C2 C8 -38.5(4) N1 C1 C2 C3 17.5(4) C11 C1 C2 C3 144.9(3) C8 C2 C3 C4 -1.8(5) C1 C2 C3 C4 174.6(3) C2 C3 C4 C6 2.1(5) C2 C3 C4 O1 177.9(3) C5 O1 C4 C3 168.0(3) C5 O1 C4 C6 -15.8(3) C6 O2 C5 O1 -26.4(4) C4 O1 C5 O2 25.9(3) C3 C4 C6 C7 -1.3(5) O1 C4 C6 C7 -177.8(3) C3 C4 C6 O2 175.9(3) O1 C4 C6 O2 -0.6(4) C5 O2 C6 C4 16.7(4) C5 O2 C6 C7 -166.2(4) C4 C6 C7 C8 0.0(5) O2 C6 C7 C8 -176.6(3) C6 C7 C8 C2 0.3(5) C6 C7 C8 C9 -178.4(3) C3 C2 C8 C7 0.7(5) C1 C2 C8 C7 -176.0(3) C3 C2 C8 C9 179.3(3) C1 C2 C8 C9 2.7(4) C7 C8 C9 C10 -148.9(3) C2 C8 C9 C10 32.5(4) C8 C9 C10 C11 -32.8(4) C9 C10 C11 C12 179.0(3) C9 C10 C11 C1 -3.2(4) N1 C1 C11 C10 167.4(3) C2 C1 C11 C10 39.3(4) N1 C1 C11 C12 -14.7(4) C2 C1 C11 C12 -142.8(3) C10 C11 C12 C13 27.4(5) C1 C11 C12 C13 -150.3(3) C10 C11 C12 C18 -152.8(3) C1 C11 C12 C18 29.5(4) C18 C12 C13 C14 -0.3(4) C11 C12 C13 C14 179.5(3) C12 C13 C14 C15 -0.1(4) C13 C14 C15 C17 0.4(4) C13 C14 C15 O3 -179.5(3) C16 O3 C15 C14 173.1(3) C16 O3 C15 C17 -6.8(3) C15 O3 C16 O4 11.5(3) C17 O4 C16 O3 -11.6(3) C14 C15 C17 C18 -0.3(5) O3 C15 C17 C18 179.6(3) C14 C15 C17 O4 179.6(3) O3 C15 C17 O4 -0.5(3) C16 O4 C17 C18 -172.5(3) C16 O4 C17 C15 7.5(3) C15 C17 C18 C12 -0.1(4) O4 C17 C18 C12 -180.0(3) C15 C17 C18 C19 -179.7(3) O4 C17 C18 C19 0.4(5) C13 C12 C18 C17 0.3(4) C11 C12 C18 C17 -179.5(3) C13 C12 C18 C19 -180.0(3) C11 C12 C18 C19 0.2(4) C20 N1 C19 C18 -118.1(3) C1 N1 C19 C18 57.3(3) C17 C18 C19 N1 138.2(3) C12 C18 C19 N1 -41.4(4) C19 N1 C20 O5 0.4(4) C1 N1 C20 O5 -174.7(3) C19 N1 C20 O6 -178.4(2) C1 N1 C20 O6 6.5(4) C21 O6 C20 O5 3.7(4) C21 O6 C20 N1 -177.5(2) C20 O6 C21 C22 -149.4(2) O6 C21 C22 C23 22.2(4) O6 C21 C22 C27 -160.3(3) C27 C22 C23 C24 0.2(5) C21 C22 C23 C24 177.6(3) C22 C23 C24 C25 -0.7(5) C23 C24 C25 C26 0.5(5) C24 C25 C26 C27 0.3(5) C25 C26 C27 C22 -0.9(5) C23 C22 C27 C26 0.6(5) C21 C22 C27 C26 -177.0(3) _journal_paper_doi 10.1021/ol300967a