#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/25/2012566.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012566 loop_ _publ_author_name 'Vasuki, G' 'Parthasarathi, V' 'Ramamurthi, K' 'Jindal, D. P' 'Dubey, S' _publ_section_title ; 4-(3,17-Dioxoandrost-4-en-16-ylidenemethyl)benzonitrile ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o162 _journal_page_last o163 _journal_paper_doi 10.1107/S0108270102000197 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C27 H29 N O2' _chemical_formula_sum 'C27 H29 N O2' _chemical_formula_weight 399.51 _chemical_name_systematic ; 4-(3,17-Dioxoandrost-4-en-16-ylidenemethyl)benzonitrile ; _space_group_IT_number 18 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2bc 2' _symmetry_space_group_name_H-M 'P 2 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.7638(10) _cell_length_b 8.4584(10) _cell_length_c 33.220(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30 _cell_measurement_theta_min 20 _cell_volume 2181.5(5) _computing_cell_refinement 'CAD-4 EXPRESS' _computing_data_collection 'CAD-4 EXPRESS (Enraf-Nonius, 1994)' _computing_data_reduction 'MolEN (Fair, 1990)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'DIRDIF98 (Beurskens et al., 1998)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .014 _diffrn_reflns_av_sigmaI/netI .021 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2365 _diffrn_reflns_theta_full 67.91 _diffrn_reflns_theta_max 67.91 _diffrn_reflns_theta_min 2.66 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .592 _exptl_absorpt_correction_T_max .943 _exptl_absorpt_correction_T_min .842 _exptl_absorpt_correction_type \y-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 856 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .10 _refine_diff_density_max .14 _refine_diff_density_min -.12 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack .9(5) _refine_ls_extinction_coef .0029(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 2363 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.108 _refine_ls_R_factor_all .052 _refine_ls_R_factor_gt .039 _refine_ls_shift/su_max .005 _refine_ls_shift/su_mean .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.2836P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt .092 _refine_ls_wR_factor_ref .105 _reflns_number_gt 1957 _reflns_number_total 2363 _reflns_threshold_expression I>2s(I) _cod_data_source_file de1179.cif _cod_data_source_block I _cod_depositor_comments ; 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 The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.2836P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.2836P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P2 21 21' _cod_database_code 2012566 _cod_database_fobs_code 2012566 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, -z' '-x, y+1/2, -z+1/2' '-x, -y+1/2, z+1/2' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 -.3161(4) -1.0084(4) -.24648(8) .0751(9) Uani d . 1 . . C H1A -.4399 -1.0233 -.2456 .090 Uiso calc R 1 . . H H1B -.2942 -.8955 -.2475 .090 Uiso calc R 1 . . H C2 -.2469(5) -1.0835(5) -.28461(9) .0905(11) Uani d . 1 . . C H2A -.2836 -1.1931 -.2857 .109 Uiso calc R 1 . . H H2B -.2951 -1.0295 -.3078 .109 Uiso calc R 1 . . H C3 -.0555(5) -1.0768(4) -.28677(9) .0747(9) Uani d . 1 . . C C4 .0336(4) -1.0807(4) -.24841(9) .0655(8) Uani d . 1 . . C H4 .1533 -1.0803 -.2488 .079 Uiso calc R 1 . . H C5 -.0439(4) -1.0847(3) -.21254(8) .0547(7) Uani d . 1 . . C C6 .0593(4) -1.1122(4) -.17502(7) .0616(7) Uani d . 1 . . C H6A .1810 -1.1037 -.1813 .074 Uiso calc R 1 . . H H6B .0378 -1.2184 -.1652 .074 Uiso calc R 1 . . H C7 .0142(3) -.9940(4) -.14231(7) .0578(7) Uani d . 1 . . C H7A .0771 -1.0201 -.1180 .069 Uiso calc R 1 . . H H7B .0494 -.8891 -.1508 .069 Uiso calc R 1 . . H C8 -.1770(3) -.9931(3) -.13326(7) .0474(6) Uani d . 1 . . C H8 -.2098 -1.0976 -.1231 .057 Uiso calc R 1 . . H C9 -.2804(3) -.9595(3) -.17214(7) .0484(6) Uani d . 1 . . C H9 -.2448 -.8541 -.1811 .058 Uiso calc R 1 . . H C10 -.2381(4) -1.0745(3) -.20766(7) .0529(6) Uani d . 1 . . C C11 -.4756(3) -.9482(4) -.16359(8) .0629(8) Uani d . 1 . . C H11A -.5339 -.9148 -.1880 .075 Uiso calc R 1 . . H H11B -.5183 -1.0525 -.1567 .075 Uiso calc R 1 . . H C12 -.5211(4) -.8337(4) -.12970(8) .0639(8) Uani d . 1 . . C H12A -.4940 -.7264 -.1379 .077 Uiso calc R 1 . . H H12B -.6436 -.8393 -.1241 .077 Uiso calc R 1 . . H C13 -.4206(3) -.8750(3) -.09201(8) .0512(6) Uani d . 1 . . C C14 -.2281(3) -.8698(3) -.10241(7) .0459(6) Uani d . 1 . . C H14 -.2089 -.7673 -.1154 .055 Uiso calc R 1 . . H C15 -.1350(4) -.8609(4) -.06158(7) .0559(7) Uani d . 1 . . C H15A -.1166 -.9655 -.0504 .067 Uiso calc R 1 . . H H15B -.0249 -.8076 -.0641 .067 Uiso calc R 1 . . H C16 -.2580(3) -.7666(3) -.03594(7) .0509(6) Uani d . 1 . . C C17 -.4295(4) -.7627(3) -.05658(8) .0554(7) Uani d . 1 . . C C18 -.4790(4) -1.0340(4) -.07394(10) .0715(9) Uani d . 1 . . C H18A -.4769 -1.1140 -.0944 .107 Uiso calc R 1 . . H H18B -.5940 -1.0236 -.0636 .107 Uiso calc R 1 . . H H18C -.4026 -1.0634 -.0525 .107 Uiso calc R 1 . . H C19 -.3070(4) -1.2417(3) -.19975(9) .0699(9) Uani d . 1 . . C H19A -.2571 -1.2823 -.1754 .105 Uiso calc R 1 . . H H19B -.2771 -1.3093 -.2219 .105 Uiso calc R 1 . . H H19C -.4300 -1.2380 -.1970 .105 Uiso calc R 1 . . H C20 -.2409(3) -.6956(3) -.00009(8) .0516(6) Uani d . 1 . . C H20 -.3419 -.6517 .0099 .062 Uiso calc R 1 . . H C21 -.0912(4) -.6756(3) .02589(7) .0512(6) Uani d . 1 . . C C22 .0775(4) -.7068(4) .01401(7) .0601(7) Uani d . 1 . . C H22 .0978 -.7482 -.0115 .072 Uiso calc R 1 . . H C23 .2143(4) -.6777(4) .03905(7) .0643(8) Uani d . 1 . . C H23 .3261 -.6975 .0303 .077 Uiso calc R 1 . . H C24 .1854(4) -.6187(3) .07737(7) .0571(7) Uani d . 1 . . C C25 .0199(4) -.5861(4) .08986(7) .0615(8) Uani d . 1 . . C H25 .0005 -.5454 .1155 .074 Uiso calc R 1 . . H C26 -.1163(4) -.6138(3) .06447(7) .0578(7) Uani d . 1 . . C H26 -.2275 -.5910 .0731 .069 Uiso calc R 1 . . H C27 .3309(5) -.5952(4) .10370(9) .0690(9) Uani d . 1 . . C N28 .4465(5) -.5835(4) .12435(9) .0941(10) Uani d . 1 . . N O29 -.5539(3) -.6869(3) -.04586(6) .0787(7) Uani d . 1 . . O O30 .0211(4) -1.0746(3) -.31863(6) .1015(9) Uani d . 1 . . O loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 .078(2) .095(2) .0520(15) -.001(2) -.0221(15) .0012(17) C2 .111(3) .111(3) .0495(16) -.007(3) -.0205(19) -.0058(19) C3 .110(3) .0641(19) .0499(16) -.010(2) .0021(18) .0044(14) C4 .071(2) .0675(19) .0583(15) -.0093(16) .0043(15) -.0007(14) C5 .0620(17) .0522(15) .0498(14) -.0090(14) -.0042(13) .0004(12) C6 .0508(15) .082(2) .0518(14) .0060(16) -.0053(13) -.0054(14) C7 .0470(14) .0753(19) .0513(14) .0012(15) -.0115(12) -.0061(14) C8 .0423(13) .0533(14) .0467(12) .0005(13) -.0085(11) .0001(11) C9 .0507(14) .0470(14) .0473(13) -.0018(12) -.0135(12) .0017(11) C10 .0560(16) .0562(15) .0465(13) -.0047(14) -.0087(12) .0004(12) C11 .0503(16) .074(2) .0646(16) .0051(15) -.0183(13) -.0079(15) C12 .0472(16) .0733(19) .0712(17) .0083(15) -.0157(14) -.0062(15) C13 .0442(14) .0533(14) .0562(14) .0002(13) -.0053(12) .0001(12) C14 .0448(13) .0468(13) .0461(12) -.0023(12) -.0087(11) .0000(11) C15 .0530(16) .0684(17) .0463(13) .0023(15) -.0095(12) -.0051(13) C16 .0543(16) .0524(15) .0461(13) -.0031(13) .0003(12) .0020(11) C17 .0525(16) .0565(16) .0570(15) .0021(15) .0019(13) .0025(13) C18 .0688(19) .0639(19) .082(2) -.0130(17) .0058(17) .0011(15) C19 .076(2) .0598(18) .0742(18) -.0167(16) .0048(17) -.0158(15) C20 .0556(14) .0492(13) .0499(12) -.0012(14) .0059(14) .0029(12) C21 .0659(17) .0437(14) .0441(12) -.0027(13) .0009(13) .0008(11) C22 .0632(17) .0735(18) .0437(13) .0024(16) -.0002(12) -.0125(13) C23 .0655(18) .079(2) .0486(14) .0064(17) -.0046(14) -.0097(14) C24 .0779(19) .0485(14) .0449(13) .0030(15) -.0122(13) -.0011(12) C25 .088(2) .0573(17) .0392(13) .0064(17) -.0016(14) -.0043(12) C26 .0699(19) .0580(16) .0456(14) .0055(16) .0048(14) -.0001(13) C27 .093(2) .0580(17) .0560(16) .0136(18) -.0224(17) -.0078(14) N28 .115(3) .083(2) .0838(18) .021(2) -.044(2) -.0177(17) O29 .0659(13) .0997(17) .0704(12) .0246(14) -.0003(11) -.0129(12) O30 .142(2) .113(2) .0501(11) -.0005(19) .0162(14) .0076(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .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 C2 C1 C10 114.2(3) yes C2 C1 H1A 108.7 ? C10 C1 H1A 108.7 ? C2 C1 H1B 108.7 ? C10 C1 H1B 108.7 ? H1A C1 H1B 107.6 ? C3 C2 C1 112.2(3) ? C3 C2 H2A 109.2 ? C1 C2 H2A 109.2 ? C3 C2 H2B 109.2 ? C1 C2 H2B 109.2 ? H2A C2 H2B 107.9 ? O30 C3 C4 122.2(3) yes O30 C3 C2 122.1(3) ? C4 C3 C2 115.6(3) ? C5 C4 C3 124.8(3) ? C5 C4 H4 117.6 ? C3 C4 H4 117.6 ? C4 C5 C6 120.4(3) ? C4 C5 C10 122.7(3) ? C6 C5 C10 116.8(2) ? C5 C6 C7 111.7(2) ? C5 C6 H6A 109.3 ? C7 C6 H6A 109.3 ? C5 C6 H6B 109.3 ? C7 C6 H6B 109.3 ? H6A C6 H6B 107.9 ? C8 C7 C6 111.8(2) ? C8 C7 H7A 109.3 ? C6 C7 H7A 109.3 ? C8 C7 H7B 109.3 ? C6 C7 H7B 109.3 ? H7A C7 H7B 107.9 ? C7 C8 C14 113.2(2) ? C7 C8 C9 110.1(2) ? C14 C8 C9 107.6(2) ? C7 C8 H8 108.6 ? C14 C8 H8 108.6 ? C9 C8 H8 108.6 ? C11 C9 C8 111.5(2) ? C11 C9 C10 112.5(2) ? C8 C9 C10 114.0(2) ? C11 C9 H9 106.0 ? C8 C9 H9 106.0 ? C10 C9 H9 106.0 ? C5 C10 C1 108.9(2) ? C5 C10 C19 108.2(2) ? C1 C10 C19 110.1(2) ? C5 C10 C9 108.9(2) ? C1 C10 C9 109.0(2) ? C19 C10 C9 111.8(2) ? C12 C11 C9 113.7(2) ? C12 C11 H11A 108.8 ? C9 C11 H11A 108.8 ? C12 C11 H11B 108.8 ? C9 C11 H11B 108.8 ? H11A C11 H11B 107.7 ? C13 C12 C11 110.1(2) ? C13 C12 H12A 109.6 ? C11 C12 H12A 109.6 ? C13 C12 H12B 109.6 ? C11 C12 H12B 109.6 ? H12A C12 H12B 108.2 ? C17 C13 C12 118.2(2) ? C17 C13 C14 101.6(2) ? C12 C13 C14 108.0(2) ? C17 C13 C18 103.4(2) ? C12 C13 C18 111.8(2) ? C14 C13 C18 113.6(2) ? C8 C14 C13 112.8(2) ? C8 C14 C15 120.5(2) ? C13 C14 C15 105.1(2) ? C8 C14 H14 105.8 ? C13 C14 H14 105.8 ? C15 C14 H14 105.8 ? C16 C15 C14 103.1(2) ? C16 C15 H15A 111.1 ? C14 C15 H15A 111.1 ? C16 C15 H15B 111.1 ? C14 C15 H15B 111.1 ? H15A C15 H15B 109.1 ? C20 C16 C17 119.0(2) ? C20 C16 C15 132.5(2) ? C17 C16 C15 108.4(2) ? O29 C17 C16 125.8(2) ? O29 C17 C13 126.6(3) ? C16 C17 C13 107.5(2) ? C13 C18 H18A 109.5 ? C13 C18 H18B 109.5 ? H18A C18 H18B 109.5 ? C13 C18 H18C 109.5 ? H18A C18 H18C 109.5 ? H18B C18 H18C 109.5 ? C10 C19 H19A 109.5 ? C10 C19 H19B 109.5 ? H19A C19 H19B 109.5 ? C10 C19 H19C 109.5 ? H19A C19 H19C 109.5 ? H19B C19 H19C 109.5 ? C16 C20 C21 131.1(2) ? C16 C20 H20 114.4 ? C21 C20 H20 114.4 ? C22 C21 C26 117.5(2) ? C22 C21 C20 124.0(2) ? C26 C21 C20 118.4(3) ? C23 C22 C21 121.5(2) ? C23 C22 H22 119.3 ? C21 C22 H22 119.3 ? C22 C23 C24 119.8(3) ? C22 C23 H23 120.1 ? C24 C23 H23 120.1 ? C25 C24 C23 120.0(3) ? C25 C24 C27 121.3(2) ? C23 C24 C27 118.7(3) ? C26 C25 C24 119.9(2) ? C26 C25 H25 120.0 ? C24 C25 H25 120.0 ? C25 C26 C21 121.3(3) ? C25 C26 H26 119.3 ? C21 C26 H26 119.3 ? N28 C27 C24 177.1(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.516(4) yes C1 C10 . 1.531(4) ? C1 H1A . .9700 ? C1 H1B . .9700 ? C2 C3 . 1.489(5) ? C2 H2A . .9700 ? C2 H2B . .9700 ? C3 O30 . 1.214(4) yes C3 C4 . 1.450(4) ? C4 C5 . 1.335(4) ? C4 H4 . .9300 ? C5 C6 . 1.500(4) ? C5 C10 . 1.519(4) ? C6 C7 . 1.518(4) ? C6 H6A . .9700 ? C6 H6B . .9700 ? C7 C8 . 1.514(4) ? C7 H7A . .9700 ? C7 H7B . .9700 ? C8 C14 . 1.515(3) ? C8 C9 . 1.547(3) ? C8 H8 . .9800 ? C9 C11 . 1.545(4) ? C9 C10 . 1.564(3) ? C9 H9 . .9800 ? C10 C19 . 1.534(4) ? C11 C12 . 1.527(4) ? C11 H11A . .9700 ? C11 H11B . .9700 ? C12 C13 . 1.516(4) ? C12 H12A . .9700 ? C12 H12B . .9700 ? C13 C17 . 1.515(4) ? C13 C14 . 1.535(4) ? C13 C18 . 1.541(4) ? C14 C15 . 1.539(3) ? C14 H14 . .9800 ? C15 C16 . 1.508(4) ? C15 H15A . .9700 ? C15 H15B . .9700 ? C16 C20 . 1.340(4) ? C16 C17 . 1.498(4) ? C17 O29 . 1.212(3) yes C18 H18A . .9600 ? C18 H18B . .9600 ? C18 H18C . .9600 ? C19 H19A . .9600 ? C19 H19B . .9600 ? C19 H19C . .9600 ? C20 C21 . 1.457(4) ? C20 H20 . .9300 ? C21 C22 . 1.393(4) ? C21 C26 . 1.397(3) ? C22 C23 . 1.372(4) ? C22 H22 . .9300 ? C23 C24 . 1.386(4) ? C23 H23 . .9300 ? C24 C25 . 1.378(4) ? C24 C27 . 1.442(4) ? C25 C26 . 1.373(4) ? C25 H25 . .9300 ? C26 H26 . .9300 ? C27 N28 . 1.134(4) ? 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 C10 C1 C2 C3 -54.1(4) yes C1 C2 C3 O30 -152.4(3) ? C1 C2 C3 C4 30.5(5) yes O30 C3 C4 C5 -179.3(3) ? C2 C3 C4 C5 -2.2(5) yes C3 C4 C5 C6 171.1(3) ? C3 C4 C5 C10 -4.3(5) yes C4 C5 C6 C7 132.3(3) ? C10 C5 C6 C7 -52.1(4) ? C5 C6 C7 C8 54.9(3) ? C6 C7 C8 C14 -176.7(2) ? C6 C7 C8 C9 -56.2(3) ? C7 C8 C9 C11 -176.7(2) ? C14 C8 C9 C11 -52.9(3) ? C7 C8 C9 C10 54.5(3) ? C14 C8 C9 C10 178.3(2) ? C4 C5 C10 C1 -17.7(4) yes C6 C5 C10 C1 166.8(2) ? C4 C5 C10 C19 101.9(3) ? C6 C5 C10 C19 -73.6(3) ? C4 C5 C10 C9 -136.4(3) ? C6 C5 C10 C9 48.0(3) ? C2 C1 C10 C5 46.1(4) yes C2 C1 C10 C19 -72.3(4) ? C2 C1 C10 C9 164.8(3) ? C11 C9 C10 C5 -177.2(2) ? C8 C9 C10 C5 -48.9(3) ? C11 C9 C10 C1 64.2(3) ? C8 C9 C10 C1 -167.6(2) ? C11 C9 C10 C19 -57.7(3) ? C8 C9 C10 C19 70.6(3) ? C8 C9 C11 C12 51.8(3) ? C10 C9 C11 C12 -178.6(2) ? C9 C11 C12 C13 -54.0(3) ? C11 C12 C13 C17 172.1(2) ? C11 C12 C13 C14 57.6(3) ? C11 C12 C13 C18 -68.1(3) ? C7 C8 C14 C13 -177.4(2) ? C9 C8 C14 C13 60.8(3) ? C7 C8 C14 C15 -52.2(3) ? C9 C8 C14 C15 -174.1(2) ? C17 C13 C14 C8 170.9(2) ? C12 C13 C14 C8 -64.0(3) ? C18 C13 C14 C8 60.6(3) ? C17 C13 C14 C15 37.8(3) ? C12 C13 C14 C15 162.9(2) ? C18 C13 C14 C15 -72.5(3) ? C8 C14 C15 C16 -161.7(2) ? C13 C14 C15 C16 -33.1(3) ? C14 C15 C16 C20 -166.8(3) ? C14 C15 C16 C17 15.3(3) ? C20 C16 C17 O29 7.9(4) ? C15 C16 C17 O29 -173.9(3) ? C20 C16 C17 C13 -169.9(2) ? C15 C16 C17 C13 8.3(3) ? C12 C13 C17 O29 36.0(4) ? C14 C13 C17 O29 154.0(3) ? C18 C13 C17 O29 -88.1(4) ? C12 C13 C17 C16 -146.2(2) ? C14 C13 C17 C16 -28.2(3) ? C18 C13 C17 C16 89.7(3) ? C17 C16 C20 C21 -177.5(3) ? C15 C16 C20 C21 4.8(5) ? C16 C20 C21 C22 11.7(5) ? C16 C20 C21 C26 -171.7(3) ? C26 C21 C22 C23 -.2(4) ? C20 C21 C22 C23 176.4(3) ? C21 C22 C23 C24 1.2(5) ? C22 C23 C24 C25 -1.5(5) ? C22 C23 C24 C27 177.5(3) ? C23 C24 C25 C26 .7(4) ? C27 C24 C25 C26 -178.2(3) ? C24 C25 C26 C21 .3(4) ? C22 C21 C26 C25 -.5(4) ? C20 C21 C26 C25 -177.4(3) ? C25 C24 C27 N28 116(7) ? C23 C24 C27 N28 -63(7) ? C17 C16 C20 H20 2.5 ? C15 C16 C20 H20 -175.2 ? H8 C8 C9 H9 179.5 ? H14 C14 C13 C18 175.8 ? C19 C10 C13 C18 7.4(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21181880 2 PubChem 12992416