#------------------------------------------------------------------------------ #$Date: 2024-10-16 03:41:16 +0300 (Wed, 16 Oct 2024) $ #$Revision: 295499 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160184.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_7160184 loop_ _publ_author_name 'Parthasarathy, Kanniyappan' 'Prabhakaran, Mohan' 'Sanjana, Ramesh' _publ_section_title ; Ruthenium-catalyzed Heck coupling of 3-arylidene-oxindoles with alkenes: a facile synthesis of 3-allylidene-2(3H)-oxindoles ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01072H _journal_year 2024 _chemical_formula_sum 'C20 H16 N O3' _chemical_formula_weight 318.34 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2024-08-24 deposited with the CCDC. 2024-10-14 downloaded from the CCDC. ; _cell_angle_alpha 119.1405(13) _cell_angle_beta 91.334(2) _cell_angle_gamma 97.5234(17) _cell_formula_units_Z 2 _cell_length_a 9.5665(4) _cell_length_b 9.9423(4) _cell_length_c 10.1434(6) _cell_measurement_reflns_used 5875 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.09 _cell_measurement_theta_min 2.36 _cell_volume 831.17(7) _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-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_unetI/netI 0.0152 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 10941 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 24.995 _diffrn_reflns_theta_max 24.995 _diffrn_reflns_theta_min 2.158 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/5(Bruker AXS.Inc)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.272 _exptl_crystal_description Block _exptl_crystal_F_000 334 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.160 _refine_diff_density_max 0.580 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 2912 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0532 _refine_ls_R_factor_gt 0.0454 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0726P)^2^+0.2461P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1215 _refine_ls_wR_factor_ref 0.1309 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2459 _reflns_number_total 2912 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01072h2.cif _cod_data_source_block 33 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_database_code 7160184 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.973 _shelx_estimated_absorpt_t_max 0.986 _shelx_res_file ; 33.res created by SHELXL-2014/7 TITL 33 in P-1 CELL 0.71073 9.56650 9.94230 10.14337 119.1405 91.3335 97.5234 ZERR 2.00 0.00040 0.00040 0.00057 0.0013 0.0023 0.0017 LATT 1 SFAC C H N O UNIT 40 32 2 6 OMIT -3 50 L.S. 8 ACTA BOND $H FMAP 2 PLAN 5 SIZE 0.160 0.280 0.320 CONF TEMP 23.000 WGHT 0.072600 0.246100 FVAR 0.22705 MOLE 1 C1 1 0.284587 0.552497 1.230241 11.00000 0.04388 0.04423 = 0.03962 0.02471 0.00545 0.00939 C2 1 0.267864 0.636109 1.382268 11.00000 0.06360 0.05970 = 0.03844 0.02823 0.00518 0.01359 AFIX 43 H2 2 0.304325 0.609867 1.450967 11.00000 -1.20000 AFIX 0 C3 1 0.195073 0.760294 1.429218 11.00000 0.08213 0.05853 = 0.03914 0.02222 0.01997 0.01900 AFIX 43 H3 2 0.183593 0.819978 1.531601 11.00000 -1.20000 AFIX 0 C4 1 0.139084 0.797285 1.326695 11.00000 0.08487 0.05485 = 0.05160 0.02899 0.02903 0.03450 AFIX 43 H4 2 0.087163 0.878870 1.360361 11.00000 -1.20000 AFIX 0 C5 1 0.159028 0.714788 1.174462 11.00000 0.06815 0.05198 = 0.04773 0.03207 0.01974 0.02724 AFIX 43 H5 2 0.121689 0.741213 1.106284 11.00000 -1.20000 AFIX 0 C6 1 0.235241 0.592406 1.124796 11.00000 0.04471 0.04023 = 0.03796 0.02393 0.00778 0.01109 C7 1 0.276796 0.482206 0.976959 11.00000 0.04064 0.03647 = 0.03864 0.02292 0.00570 0.01149 C8 1 0.345186 0.367357 1.003887 11.00000 0.04621 0.04114 = 0.04096 0.02543 0.00589 0.01457 C9 1 0.268274 0.483444 0.843262 11.00000 0.03989 0.03686 = 0.03867 0.02230 0.00536 0.01044 C10 1 0.214076 0.613500 0.834778 11.00000 0.04691 0.04076 = 0.03386 0.02337 0.01216 0.01718 C11 1 0.297453 0.759517 0.896043 11.00000 0.05277 0.04423 = 0.04704 0.02466 0.00951 0.01537 AFIX 43 H11 2 0.388302 0.776326 0.941604 11.00000 -1.20000 AFIX 0 C12 1 0.246086 0.880301 0.889689 11.00000 0.07186 0.04115 = 0.05893 0.02948 0.02366 0.01956 AFIX 43 H12 2 0.303249 0.977523 0.931407 11.00000 -1.20000 AFIX 0 C13 1 0.111823 0.859603 0.822763 11.00000 0.07566 0.05857 = 0.05537 0.04062 0.03202 0.03984 C14 1 0.030320 0.713501 0.760668 11.00000 0.05736 0.07744 = 0.07062 0.04711 0.00975 0.03256 AFIX 43 H14 2 -0.060272 0.696754 0.714581 11.00000 -1.20000 AFIX 0 C15 1 0.080494 0.591027 0.765448 11.00000 0.04937 0.05238 = 0.06308 0.03444 0.00304 0.01393 AFIX 43 H15 2 0.023910 0.493324 0.721761 11.00000 -1.20000 AFIX 0 C16 1 0.055589 0.992694 0.818244 11.00000 0.11797 0.08755 = 0.09634 0.06746 0.04903 0.07005 AFIX 137 H16A 2 0.052869 1.075404 0.919932 11.00000 -1.50000 H16B 2 -0.038278 0.956450 0.766385 11.00000 -1.50000 H16C 2 0.116479 1.030720 0.765547 11.00000 -1.50000 AFIX 0 C17 1 0.315160 0.363077 0.706290 11.00000 0.04957 0.03871 = 0.03927 0.02322 0.00515 0.01399 AFIX 43 H17 2 0.344239 0.278968 0.709517 11.00000 -1.20000 AFIX 0 C18 1 0.318995 0.365887 0.577037 11.00000 0.06778 0.04774 = 0.04326 0.02838 0.01070 0.02528 AFIX 43 H18 2 0.284619 0.447202 0.572974 11.00000 -1.20000 AFIX 0 C19 1 0.373163 0.250883 0.440149 11.00000 0.06673 0.05340 = 0.03677 0.02711 0.00738 0.02102 C20 1 0.465249 0.015482 0.320288 11.00000 0.09450 0.05536 = 0.04564 0.01927 0.02209 0.03211 AFIX 137 H20A 2 0.404470 -0.020073 0.229079 11.00000 -1.50000 H20B 2 0.475049 -0.071376 0.334890 11.00000 -1.50000 H20C 2 0.556735 0.061886 0.311963 11.00000 -1.50000 AFIX 0 N1 3 0.349581 0.419973 1.156081 11.00000 0.05475 0.05073 = 0.04204 0.02915 0.00612 0.02006 O1 4 0.391011 0.251315 0.913768 11.00000 0.08217 0.05236 = 0.05023 0.02921 0.01320 0.03723 O2 4 0.390907 0.266918 0.331208 11.00000 0.16094 0.10029 = 0.05327 0.05647 0.04317 0.07446 O3 4 0.404245 0.129960 0.448203 11.00000 0.08813 0.04607 = 0.03864 0.02279 0.01883 0.02914 HKLF 4 REM 33 in P-1 REM R1 = 0.0454 for 2459 Fo > 4sig(Fo) and 0.0532 for all 2912 data REM 219 parameters refined using 0 restraints END WGHT 0.0726 0.2461 REM Highest difference peak 0.580, deepest hole -0.231, 1-sigma level 0.049 Q1 1 0.3778 0.3633 1.1992 11.00000 0.05 0.58 Q2 1 -0.0456 1.0042 0.8579 11.00000 0.05 0.18 Q3 1 -0.0033 0.9263 0.6754 11.00000 0.05 0.15 Q4 1 0.3279 0.5154 0.9267 11.00000 0.05 0.15 Q5 1 0.1643 1.1051 0.8343 11.00000 0.05 0.13 ; _shelx_res_checksum 49012 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.28459(17) 0.55250(19) 1.23024(18) 0.0406(4) Uani 1 1 d . . . . . C2 C 0.2679(2) 0.6361(2) 1.3823(2) 0.0518(5) Uani 1 1 d . . . . . H2 H 0.3043 0.6099 1.4510 0.062 Uiso 1 1 calc R U . . . C3 C 0.1951(2) 0.7603(2) 1.4292(2) 0.0597(5) Uani 1 1 d . . . . . H3 H 0.1836 0.8200 1.5316 0.072 Uiso 1 1 calc R U . . . C4 C 0.1391(2) 0.7973(2) 1.3267(2) 0.0598(5) Uani 1 1 d . . . . . H4 H 0.0872 0.8789 1.3604 0.072 Uiso 1 1 calc R U . . . C5 C 0.1590(2) 0.7148(2) 1.1745(2) 0.0507(5) Uani 1 1 d . . . . . H5 H 0.1217 0.7412 1.1063 0.061 Uiso 1 1 calc R U . . . C6 C 0.23524(17) 0.59241(19) 1.12480(18) 0.0385(4) Uani 1 1 d . . . . . C7 C 0.27680(16) 0.48221(18) 0.97696(18) 0.0361(4) Uani 1 1 d . . . . . C8 C 0.34519(17) 0.36736(19) 1.00389(18) 0.0398(4) Uani 1 1 d . . . . . C9 C 0.26827(16) 0.48344(18) 0.84326(18) 0.0364(4) Uani 1 1 d . . . . . C10 C 0.21408(17) 0.61350(18) 0.83478(17) 0.0372(4) Uani 1 1 d . . . . . C11 C 0.29745(19) 0.7595(2) 0.8960(2) 0.0463(4) Uani 1 1 d . . . . . H11 H 0.3883 0.7763 0.9416 0.056 Uiso 1 1 calc R U . . . C12 C 0.2461(2) 0.8803(2) 0.8897(2) 0.0539(5) Uani 1 1 d . . . . . H12 H 0.3032 0.9775 0.9314 0.065 Uiso 1 1 calc R U . . . C13 C 0.1118(2) 0.8596(2) 0.8228(2) 0.0544(5) Uani 1 1 d . . . . . C14 C 0.0303(2) 0.7135(3) 0.7607(2) 0.0616(5) Uani 1 1 d . . . . . H14 H -0.0603 0.6968 0.7146 0.074 Uiso 1 1 calc R U . . . C15 C 0.08049(19) 0.5910(2) 0.7654(2) 0.0519(5) Uani 1 1 d . . . . . H15 H 0.0239 0.4933 0.7218 0.062 Uiso 1 1 calc R U . . . C16 C 0.0556(3) 0.9927(3) 0.8182(3) 0.0849(8) Uani 1 1 d . . . . . H16A H 0.0529 1.0754 0.9199 0.127 Uiso 1 1 calc R U . . . H16B H -0.0383 0.9564 0.7664 0.127 Uiso 1 1 calc R U . . . H16C H 0.1165 1.0307 0.7655 0.127 Uiso 1 1 calc R U . . . C17 C 0.31516(17) 0.36308(19) 0.70629(18) 0.0401(4) Uani 1 1 d . . . . . H17 H 0.3442 0.2790 0.7095 0.048 Uiso 1 1 calc R U . . . C18 C 0.3190(2) 0.3659(2) 0.57704(19) 0.0487(4) Uani 1 1 d . . . . . H18 H 0.2846 0.4472 0.5730 0.058 Uiso 1 1 calc R U . . . C19 C 0.3732(2) 0.2509(2) 0.44015(19) 0.0490(4) Uani 1 1 d . . . . . C20 C 0.4652(3) 0.0155(2) 0.3203(2) 0.0653(6) Uani 1 1 d . . . . . H20A H 0.4045 -0.0201 0.2291 0.098 Uiso 1 1 calc R U . . . H20B H 0.4750 -0.0714 0.3349 0.098 Uiso 1 1 calc R U . . . H20C H 0.5567 0.0619 0.3120 0.098 Uiso 1 1 calc R U . . . N1 N 0.34958(15) 0.41997(17) 1.15608(16) 0.0453(4) Uani 1 1 d . . . . . O1 O 0.39101(15) 0.25132(15) 0.91377(14) 0.0571(4) Uani 1 1 d . . . . . O2 O 0.3909(2) 0.2669(2) 0.33121(17) 0.0908(6) Uani 1 1 d . . . . . O3 O 0.40424(15) 0.12996(14) 0.44820(13) 0.0547(4) Uani 1 1 d . . . . . 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 0.0439(9) 0.0442(9) 0.0396(9) 0.0247(7) 0.0055(7) 0.0094(7) C2 0.0636(11) 0.0597(11) 0.0384(9) 0.0282(9) 0.0052(8) 0.0136(9) C3 0.0821(14) 0.0585(12) 0.0391(10) 0.0222(9) 0.0200(9) 0.0190(10) C4 0.0849(14) 0.0548(11) 0.0516(11) 0.0290(9) 0.0290(10) 0.0345(10) C5 0.0682(12) 0.0520(10) 0.0477(10) 0.0321(9) 0.0197(9) 0.0272(9) C6 0.0447(9) 0.0402(8) 0.0380(8) 0.0239(7) 0.0078(7) 0.0111(7) C7 0.0406(8) 0.0365(8) 0.0386(8) 0.0229(7) 0.0057(6) 0.0115(7) C8 0.0462(9) 0.0411(9) 0.0410(9) 0.0254(7) 0.0059(7) 0.0146(7) C9 0.0399(8) 0.0369(8) 0.0387(8) 0.0223(7) 0.0054(6) 0.0104(6) C10 0.0469(9) 0.0408(9) 0.0339(8) 0.0234(7) 0.0122(7) 0.0172(7) C11 0.0528(10) 0.0442(9) 0.0470(10) 0.0247(8) 0.0095(8) 0.0154(8) C12 0.0719(13) 0.0412(10) 0.0589(11) 0.0295(9) 0.0237(9) 0.0196(9) C13 0.0757(13) 0.0586(12) 0.0554(11) 0.0406(10) 0.0320(10) 0.0398(10) C14 0.0574(11) 0.0774(14) 0.0706(13) 0.0471(12) 0.0097(10) 0.0326(11) C15 0.0494(10) 0.0524(11) 0.0631(12) 0.0344(9) 0.0030(8) 0.0139(8) C16 0.118(2) 0.0875(17) 0.0963(18) 0.0675(15) 0.0490(16) 0.0701(16) C17 0.0496(9) 0.0387(8) 0.0393(9) 0.0232(7) 0.0052(7) 0.0140(7) C18 0.0678(11) 0.0477(10) 0.0433(10) 0.0284(8) 0.0107(8) 0.0253(9) C19 0.0667(11) 0.0534(10) 0.0368(9) 0.0271(8) 0.0074(8) 0.0210(9) C20 0.0945(16) 0.0554(12) 0.0456(11) 0.0193(9) 0.0221(10) 0.0321(11) N1 0.0547(8) 0.0507(8) 0.0420(8) 0.0291(7) 0.0061(6) 0.0201(7) O1 0.0822(9) 0.0524(8) 0.0502(7) 0.0292(6) 0.0132(6) 0.0372(7) O2 0.1609(17) 0.1003(12) 0.0533(9) 0.0565(9) 0.0432(10) 0.0745(12) O3 0.0881(10) 0.0461(7) 0.0386(7) 0.0228(6) 0.0188(6) 0.0291(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 N1 127.84(15) . . ? C2 C1 C6 122.52(16) . . ? N1 C1 C6 109.64(14) . . ? C1 C2 C3 117.64(17) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? C4 C3 C2 121.03(17) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 120.96(17) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 119.24(17) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C5 C6 C1 118.47(15) . . ? C5 C6 C7 134.35(15) . . ? C1 C6 C7 107.15(13) . . ? C9 C7 C6 129.49(14) . . ? C9 C7 C8 125.02(14) . . ? C6 C7 C8 105.32(12) . . ? O1 C8 N1 124.21(14) . . ? O1 C8 C7 129.55(15) . . ? N1 C8 C7 106.23(13) . . ? C7 C9 C17 121.96(14) . . ? C7 C9 C10 120.32(14) . . ? C17 C9 C10 117.69(13) . . ? C15 C10 C11 118.63(15) . . ? C15 C10 C9 120.85(15) . . ? C11 C10 C9 120.52(14) . . ? C12 C11 C10 120.33(17) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 121.45(18) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C14 C13 C12 117.78(16) . . ? C14 C13 C16 121.1(2) . . ? C12 C13 C16 121.2(2) . . ? C13 C14 C15 121.48(18) . . ? C13 C14 H14 119.3 . . ? C15 C14 H14 119.3 . . ? C10 C15 C14 120.32(18) . . ? C10 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C9 124.01(15) . . ? C18 C17 H17 118.0 . . ? C9 C17 H17 118.0 . . ? C17 C18 C19 125.09(15) . . ? C17 C18 H18 117.5 . . ? C19 C18 H18 117.5 . . ? O2 C19 O3 122.79(17) . . ? O2 C19 C18 123.22(16) . . ? O3 C19 C18 113.97(14) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C8 N1 C1 111.46(13) . . ? C19 O3 C20 117.09(14) . . ? 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 C1 C2 1.376(2) . ? C1 N1 1.400(2) . ? C1 C6 1.401(2) . ? C2 C3 1.380(3) . ? C2 H2 0.9300 . ? C3 C4 1.379(3) . ? C3 H3 0.9300 . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 C6 1.385(2) . ? C5 H5 0.9300 . ? C6 C7 1.466(2) . ? C7 C9 1.363(2) . ? C7 C8 1.516(2) . ? C8 O1 1.218(2) . ? C8 N1 1.365(2) . ? C9 C17 1.454(2) . ? C9 C10 1.493(2) . ? C10 C15 1.381(2) . ? C10 C11 1.387(2) . ? C11 C12 1.384(2) . ? C11 H11 0.9300 . ? C12 C13 1.381(3) . ? C12 H12 0.9300 . ? C13 C14 1.380(3) . ? C13 C16 1.512(2) . ? C14 C15 1.387(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.326(2) . ? C17 H17 0.9300 . ? C18 C19 1.465(2) . ? C18 H18 0.9300 . ? C19 O2 1.204(2) . ? C19 O3 1.315(2) . ? C20 O3 1.446(2) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 N1 C1 C2 C3 -177.61(17) . . . . ? C6 C1 C2 C3 2.3(3) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C2 C3 C4 C5 -2.6(3) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C1 2.6(3) . . . . ? C4 C5 C6 C7 -179.91(18) . . . . ? C2 C1 C6 C5 -4.1(3) . . . . ? N1 C1 C6 C5 175.76(15) . . . . ? C2 C1 C6 C7 177.72(16) . . . . ? N1 C1 C6 C7 -2.37(19) . . . . ? C5 C6 C7 C9 10.9(3) . . . . ? C1 C6 C7 C9 -171.42(16) . . . . ? C5 C6 C7 C8 -173.63(19) . . . . ? C1 C6 C7 C8 4.06(17) . . . . ? C9 C7 C8 O1 -7.6(3) . . . . ? C6 C7 C8 O1 176.69(18) . . . . ? C9 C7 C8 N1 171.37(15) . . . . ? C6 C7 C8 N1 -4.38(17) . . . . ? C6 C7 C9 C17 179.99(15) . . . . ? C8 C7 C9 C17 5.3(3) . . . . ? C6 C7 C9 C10 2.0(3) . . . . ? C8 C7 C9 C10 -172.63(14) . . . . ? C7 C9 C10 C15 -105.91(19) . . . . ? C17 C9 C10 C15 76.1(2) . . . . ? C7 C9 C10 C11 74.4(2) . . . . ? C17 C9 C10 C11 -103.67(18) . . . . ? C15 C10 C11 C12 1.1(2) . . . . ? C9 C10 C11 C12 -179.15(15) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C11 C12 C13 C16 179.10(17) . . . . ? C12 C13 C14 C15 0.3(3) . . . . ? C16 C13 C14 C15 -179.42(18) . . . . ? C11 C10 C15 C14 -1.4(3) . . . . ? C9 C10 C15 C14 178.84(16) . . . . ? C13 C14 C15 C10 0.7(3) . . . . ? C7 C9 C17 C18 -174.62(17) . . . . ? C10 C9 C17 C18 3.4(2) . . . . ? C9 C17 C18 C19 176.37(17) . . . . ? C17 C18 C19 O2 -170.7(2) . . . . ? C17 C18 C19 O3 7.6(3) . . . . ? O1 C8 N1 C1 -177.88(16) . . . . ? C7 C8 N1 C1 3.11(18) . . . . ? C2 C1 N1 C8 179.36(17) . . . . ? C6 C1 N1 C8 -0.5(2) . . . . ? O2 C19 O3 C20 1.5(3) . . . . ? C18 C19 O3 C20 -176.87(17) . . . . ?