#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/39/2013988.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_2013988 loop_ _publ_author_name 'Ko\;sar, Ba\;sak' 'B\"uy\"ukg\"ung\"or, Orhan' 'Albayrak, \,Ci\(gdem' 'Odaba\,so\(glu, Mustafa' _publ_section_title ; 3-Hydroxy-6-[(4-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone and 2-hydroxy-6-[(4-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o458 _journal_page_last o460 _journal_paper_doi 10.1107/S0108270104010832 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C13 H11 N O3' _chemical_formula_moiety 'C13 H11 N O3' _chemical_formula_sum 'C13 H11 N O3' _chemical_formula_weight 229.23 _chemical_melting_point 465.0(10) _chemical_name_systematic ; 2-Hydroxy-6-[(4-hydroxyphenylamino)methylene]cyclohexa-2,4-dienone ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 96.693(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 12.6440(8) _cell_length_b 8.3499(3) _cell_length_c 20.1529(12) _cell_measurement_reflns_used 22130 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.12 _cell_measurement_theta_min 1.62 _cell_volume 2113.2(2) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Stoe IPDS 2' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 32250 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.62 _diffrn_standards_decay_% <2 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.9853 _exptl_absorpt_correction_T_min 0.9496 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED; Stoe & Cie, 2002)' _exptl_crystal_colour 'dark red' _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description shapeless _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.21 _refine_diff_density_max 0.208 _refine_diff_density_min -0.148 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 339 _refine_ls_number_reflns 4610 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 2.501 _refine_ls_R_factor_all 0.0529 _refine_ls_R_factor_gt 0.0341 _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^)+(0.0592P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0872 _refine_ls_wR_factor_ref 0.0930 _reflns_number_gt 3305 _reflns_number_total 4610 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1477.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '464-466' was changed to '465.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '464-466' was changed to '465.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 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_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2013988 _cod_database_fobs_code 2013988 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' '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 -0.0008(2) 0.3052(4) 0.62303(14) 0.0369(6) Uani d . 1 . . C C2 -0.0798(3) 0.1913(4) 0.61224(15) 0.0421(7) Uani d . 1 . . C H2 -0.0936 0.1426 0.5706 0.051 Uiso calc RD 1 . . H C3 -0.1385(3) 0.1494(4) 0.66353(16) 0.0428(7) Uani d . 1 . . C H3 -0.1913 0.0718 0.6564 0.051 Uiso calc R 1 . . H C4 -0.1189(2) 0.2224(4) 0.72512(15) 0.0393(7) Uani d . 1 . . C C5 -0.0382(3) 0.3334(4) 0.73661(16) 0.0464(8) Uani d . 1 . . C H5 -0.0232 0.3803 0.7785 0.056 Uiso calc R 1 . . H C6 0.0202(3) 0.3746(4) 0.68545(16) 0.0456(8) Uani d . 1 . . C H6 0.0743 0.4500 0.6931 0.055 Uiso calc R 1 . . H C7 0.0655(3) 0.2914(4) 0.51594(15) 0.0412(7) Uani d . 1 . . C C8 0.1307(2) 0.3521(4) 0.46839(14) 0.0387(7) Uani d . 1 . . C C9 0.1352(3) 0.2697(4) 0.40780(15) 0.0472(8) Uani d . 1 . . C H9 0.0929 0.1796 0.3980 0.057 Uiso calc R 1 . . H C10 0.2014(3) 0.3213(4) 0.36333(16) 0.0502(8) Uani d . 1 . . C H10 0.2036 0.2667 0.3233 0.060 Uiso calc R 1 . . H C11 0.2656(3) 0.4555(4) 0.37768(15) 0.0461(8) Uani d . 1 . . C H11 0.3113 0.4887 0.3474 0.055 Uiso calc R 1 . . H C12 0.2621(2) 0.5391(4) 0.43600(15) 0.0413(7) Uani d . 1 . . C C13 0.1930(2) 0.4912(4) 0.48274(14) 0.0388(7) Uani d . 1 . . C C14 0.4561(2) 0.1462(4) 0.40719(14) 0.0384(7) Uani d . 1 . . C C15 0.5280(3) 0.2697(4) 0.40289(15) 0.0436(7) Uani d . 1 . . C H15 0.5396 0.3442 0.4372 0.052 Uiso calc R 1 . . H C16 0.5825(3) 0.2822(4) 0.34782(16) 0.0440(7) Uani d . 1 . . C H16 0.6315 0.3645 0.3453 0.053 Uiso calc R 1 . . H C17 0.5646(2) 0.1726(4) 0.29609(15) 0.0406(7) Uani d . 1 . . C C18 0.4926(3) 0.0501(4) 0.30019(15) 0.0470(8) Uani d . 1 . . C H18 0.4800 -0.0232 0.2654 0.056 Uiso calc R 1 . . H C19 0.4394(3) 0.0362(4) 0.35565(16) 0.0461(8) Uani d . 1 . . C H19 0.3919 -0.0478 0.3586 0.055 Uiso calc R 1 . . H C20 0.4032(3) 0.2071(4) 0.51721(16) 0.0441(7) Uani d . 1 . . C C21 0.3415(3) 0.1677(4) 0.56900(15) 0.0407(7) Uani d . 1 . . C C22 0.3480(3) 0.2610(4) 0.62764(17) 0.0515(8) Uani d . 1 . . C H22 0.3925 0.3500 0.6319 0.062 Uiso calc R 1 . . H C23 0.2899(3) 0.2224(4) 0.67815(17) 0.0537(9) Uani d . 1 . . C H23 0.2942 0.2859 0.7163 0.064 Uiso calc R 1 . . H C24 0.2241(3) 0.0878(4) 0.67287(16) 0.0486(8) Uani d . 1 . . C H24 0.1846 0.0618 0.7075 0.058 Uiso calc R 1 . . H C25 0.2175(2) -0.0057(4) 0.61718(15) 0.0424(7) Uani d . 1 . . C C26 0.2743(2) 0.0304(4) 0.56259(14) 0.0391(7) Uani d . 1 . . C N1 0.0604(2) 0.3593(3) 0.57287(12) 0.0401(6) Uani d . 1 . . N N2 0.3989(2) 0.1228(3) 0.46264(12) 0.0414(6) Uani d . 1 . . N O1 -0.18331(19) 0.1816(3) 0.77327(12) 0.0491(6) Uani d . 1 . . O O2 0.1889(2) 0.5753(3) 0.53811(11) 0.0508(6) Uani d D 1 . . O O3 0.3262(2) 0.6695(3) 0.44918(13) 0.0561(7) Uani d . 1 . . O O4 0.6154(2) 0.1805(3) 0.24005(12) 0.0532(6) Uani d . 1 . . O O5 0.2637(2) -0.0606(3) 0.50998(10) 0.0493(6) Uani d . 1 . . O O6 0.1550(2) -0.1422(3) 0.61175(12) 0.0540(6) Uani d . 1 . . O H1 0.098(5) 0.448(7) 0.580(3) 0.14(2) Uiso d D 1 . . H H4 0.343(4) 0.031(6) 0.464(2) 0.083(14) Uiso d . 1 . . H H7 0.025(3) 0.192(4) 0.5044(17) 0.046(9) Uiso d . 1 . . H H20 0.452(3) 0.298(5) 0.5241(18) 0.057(10) Uiso d . 1 . . H H33 0.301(4) 0.733(7) 0.481(3) 0.103(18) Uiso d . 1 . . H H44 0.676(4) 0.240(7) 0.249(2) 0.097(17) Uiso d . 1 . . H H66 0.169(4) -0.198(7) 0.577(3) 0.101(18) Uiso d . 1 . . H H77 -0.164(4) 0.243(6) 0.810(2) 0.089(15) Uiso d . 1 . . H 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 0.0394(15) 0.0364(15) 0.0360(15) 0.0018(13) 0.0097(12) 0.0025(11) C2 0.0467(17) 0.0448(17) 0.0358(15) -0.0044(14) 0.0085(13) -0.0039(12) C3 0.0427(16) 0.0421(17) 0.0451(17) -0.0051(14) 0.0111(13) -0.0005(13) C4 0.0407(15) 0.0399(16) 0.0394(15) 0.0077(13) 0.0137(12) 0.0065(12) C5 0.0501(18) 0.0535(19) 0.0368(16) -0.0020(16) 0.0106(13) -0.0078(14) C6 0.0462(17) 0.0482(18) 0.0438(17) -0.0096(15) 0.0114(14) -0.0081(13) C7 0.0462(17) 0.0379(16) 0.0406(16) -0.0003(14) 0.0101(13) -0.0001(13) C8 0.0438(16) 0.0382(16) 0.0352(14) 0.0025(13) 0.0093(12) 0.0030(12) C9 0.059(2) 0.0423(18) 0.0412(16) -0.0030(15) 0.0115(14) -0.0036(13) C10 0.068(2) 0.0482(19) 0.0370(16) 0.0052(17) 0.0168(15) -0.0023(14) C11 0.0513(18) 0.052(2) 0.0382(15) 0.0062(15) 0.0178(14) 0.0073(14) C12 0.0409(16) 0.0428(17) 0.0412(16) 0.0013(13) 0.0082(13) 0.0061(13) C13 0.0436(16) 0.0405(16) 0.0330(14) 0.0030(13) 0.0079(12) 0.0026(12) C14 0.0393(15) 0.0411(16) 0.0353(15) 0.0019(13) 0.0071(12) 0.0026(12) C15 0.0512(18) 0.0401(17) 0.0406(16) -0.0024(14) 0.0105(13) -0.0036(13) C16 0.0478(17) 0.0396(17) 0.0462(17) -0.0045(14) 0.0126(14) 0.0016(13) C17 0.0408(16) 0.0451(17) 0.0367(15) 0.0059(13) 0.0087(12) 0.0032(12) C18 0.0491(18) 0.052(2) 0.0398(16) -0.0042(15) 0.0071(13) -0.0100(14) C19 0.0457(17) 0.0473(19) 0.0460(17) -0.0087(14) 0.0076(14) -0.0039(14) C20 0.0489(18) 0.0416(17) 0.0429(17) -0.0022(15) 0.0099(14) -0.0004(13) C21 0.0459(17) 0.0386(16) 0.0388(15) 0.0024(13) 0.0095(13) 0.0019(12) C22 0.062(2) 0.0424(18) 0.0523(19) -0.0047(16) 0.0154(16) -0.0083(15) C23 0.067(2) 0.051(2) 0.0460(18) 0.0019(17) 0.0177(16) -0.0104(15) C24 0.0543(19) 0.0517(19) 0.0424(17) 0.0051(16) 0.0173(14) 0.0022(14) C25 0.0432(17) 0.0430(17) 0.0418(16) 0.0015(14) 0.0079(13) 0.0059(13) C26 0.0437(16) 0.0408(16) 0.0326(14) 0.0038(13) 0.0042(12) 0.0035(12) N1 0.0450(14) 0.0398(14) 0.0372(13) -0.0025(12) 0.0118(11) 0.0012(11) N2 0.0447(14) 0.0430(14) 0.0377(13) -0.0027(12) 0.0104(11) 0.0029(11) O1 0.0546(14) 0.0513(14) 0.0459(13) 0.0041(11) 0.0242(11) 0.0048(11) O2 0.0658(15) 0.0485(13) 0.0409(12) -0.0134(11) 0.0181(10) -0.0081(10) O3 0.0578(15) 0.0611(16) 0.0526(14) -0.0166(13) 0.0207(12) -0.0046(12) O4 0.0561(15) 0.0641(16) 0.0424(13) 0.0000(13) 0.0190(11) -0.0017(11) O5 0.0640(15) 0.0481(13) 0.0365(11) -0.0123(11) 0.0080(10) -0.0028(10) O6 0.0624(15) 0.0569(15) 0.0457(13) -0.0154(12) 0.0190(11) -0.0013(11) 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_publ_flag C2 C1 C6 119.4(3) ? C2 C1 N1 123.6(3) ? C6 C1 N1 116.9(3) ? C1 C2 C3 119.9(3) ? C1 C2 H2 120.1 ? C3 C2 H2 120.1 ? C4 C3 C2 120.3(3) ? C4 C3 H3 119.9 ? C2 C3 H3 119.9 ? C5 C4 C3 120.0(3) ? C5 C4 O1 122.3(3) ? C3 C4 O1 117.7(3) ? C4 C5 C6 119.5(3) ? C4 C5 H5 120.3 ? C6 C5 H5 120.3 ? C5 C6 C1 120.9(3) ? C5 C6 H6 119.6 ? C1 C6 H6 119.6 ? N1 C7 C8 122.3(3) ? N1 C7 H7 120(2) ? C8 C7 H7 118(2) ? C9 C8 C13 120.0(3) ? C9 C8 C7 119.5(3) yes C13 C8 C7 120.4(3) yes C10 C9 C8 120.3(3) ? C10 C9 H9 119.9 ? C8 C9 H9 119.9 ? C9 C10 C11 120.3(3) ? C9 C10 H10 119.9 ? C11 C10 H10 119.9 ? C12 C11 C10 120.7(3) ? C12 C11 H11 119.7 ? C10 C11 H11 119.7 ? O3 C12 C11 119.6(3) ? O3 C12 C13 119.7(3) ? C11 C12 C13 120.7(3) ? O2 C13 C12 120.0(3) yes O2 C13 C8 122.1(3) yes C12 C13 C8 117.9(3) ? C15 C14 C19 119.4(3) ? C15 C14 N2 123.6(3) ? C19 C14 N2 117.0(3) ? C16 C15 C14 120.1(3) ? C16 C15 H15 120.0 ? C14 C15 H15 120.0 ? C15 C16 C17 120.2(3) ? C15 C16 H16 119.9 ? C17 C16 H16 119.9 ? O4 C17 C18 117.6(3) ? O4 C17 C16 122.6(3) ? C18 C17 C16 119.8(3) ? C19 C18 C17 120.0(3) ? C19 C18 H18 120.0 ? C17 C18 H18 120.0 ? C18 C19 C14 120.5(3) ? C18 C19 H19 119.7 ? C14 C19 H19 119.7 ? N2 C20 C21 121.7(3) ? N2 C20 H20 120(2) ? C21 C20 H20 118(2) ? C22 C21 C20 120.5(3) ? C22 C21 C26 119.8(3) ? C20 C21 C26 119.7(3) ? C23 C22 C21 120.8(3) ? C23 C22 H22 119.6 ? C21 C22 H22 119.6 ? C22 C23 C24 120.2(3) ? C22 C23 H23 119.9 ? C24 C23 H23 119.9 ? C25 C24 C23 120.2(3) ? C25 C24 H24 119.9 ? C23 C24 H24 119.9 ? C24 C25 O6 121.1(3) ? C24 C25 C26 122.0(3) ? O6 C25 C26 116.8(3) ? O5 C26 C25 119.8(3) ? O5 C26 C21 123.3(3) ? C25 C26 C21 116.9(3) ? C7 N1 C1 125.7(3) ? C7 N1 H1 115(4) ? C1 N1 H1 119(4) ? C20 N2 C14 128.2(3) ? C20 N2 H4 110(2) ? C14 N2 H4 122(2) ? C4 O1 H77 107(3) ? C12 O3 H33 111(3) ? C17 O4 H44 109(3) ? C25 O6 H66 110(4) ? 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 . 1.378(4) ? C1 C6 . 1.382(4) ? C1 N1 . 1.416(4) yes C2 C3 . 1.386(4) ? C2 H2 . 0.9300 ? C3 C4 . 1.379(4) ? C3 H3 . 0.9300 ? C4 C5 . 1.378(5) ? C4 O1 . 1.381(3) yes C5 C6 . 1.380(4) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? C7 N1 . 1.288(4) yes C7 C8 . 1.428(4) yes C7 H7 . 0.99(4) ? C8 C9 . 1.409(4) ? C8 C13 . 1.415(4) ? C9 C10 . 1.365(5) ? C9 H9 . 0.9300 ? C10 C11 . 1.394(5) ? C10 H10 . 0.9300 ? C11 C12 . 1.372(4) ? C11 H11 . 0.9300 ? C12 O3 . 1.365(4) yes C12 C13 . 1.415(4) ? C13 O2 . 1.324(4) yes C14 C15 . 1.384(4) ? C14 C19 . 1.384(4) ? C14 N2 . 1.414(4) ? C15 C16 . 1.377(4) ? C15 H15 . 0.9300 ? C16 C17 . 1.386(5) ? C16 H16 . 0.9300 ? C17 O4 . 1.364(4) ? C17 C18 . 1.378(5) ? C18 C19 . 1.375(4) ? C18 H18 . 0.9300 ? C19 H19 . 0.9300 ? C20 N2 . 1.301(4) ? C20 C21 . 1.413(4) ? C20 H20 . 0.98(4) ? C21 C22 . 1.410(4) ? C21 C26 . 1.423(4) ? C22 C23 . 1.361(5) ? C22 H22 . 0.9300 ? C23 C24 . 1.396(5) ? C23 H23 . 0.9300 ? C24 C25 . 1.362(5) ? C24 H24 . 0.9300 ? C25 O6 . 1.384(4) ? C25 C26 . 1.415(4) ? C26 O5 . 1.298(4) ? N1 H1 . 0.88(5) ? N2 H4 . 1.04(5) ? O1 H77 . 0.90(5) ? O3 H33 . 0.92(5) ? O4 H44 . 0.91(5) ? O6 H66 . 0.88(5) ? 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_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H4 O5 . 1.04(5) 1.64(5) 2.561(3) 145(4) N1 H1 O2 . 0.88(5) 1.84(4) 2.578(3) 141(6) O6 H66 O5 . 0.88(5) 2.22(5) 2.686(3) 112(4) O1 H77 O6 2_556 0.90(5) 1.85(5) 2.733(4) 167(4) O6 H66 O2 1_545 0.88(5) 2.07(6) 2.846(4) 146(5) O4 H44 O1 4_665 0.91(5) 1.90(5) 2.803(4) 167(5) O3 H33 O5 1_565 0.92(5) 1.89(6) 2.727(4) 150(5) 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 C6 C1 C2 C3 1.1(5) ? N1 C1 C2 C3 -177.6(3) ? C1 C2 C3 C4 0.6(5) ? C2 C3 C4 C5 -2.2(5) ? C2 C3 C4 O1 176.9(3) ? C3 C4 C5 C6 2.1(5) ? O1 C4 C5 C6 -177.0(3) ? C4 C5 C6 C1 -0.4(5) ? C2 C1 C6 C5 -1.2(5) ? N1 C1 C6 C5 177.6(3) ? N1 C7 C8 C9 178.2(3) ? N1 C7 C8 C13 0.2(5) yes C13 C8 C9 C10 1.4(5) ? C7 C8 C9 C10 -176.5(3) ? C8 C9 C10 C11 0.4(5) ? C9 C10 C11 C12 -1.1(5) ? C10 C11 C12 O3 179.5(3) ? C10 C11 C12 C13 -0.2(5) ? O3 C12 C13 O2 1.8(5) ? C11 C12 C13 O2 -178.5(3) ? O3 C12 C13 C8 -177.7(3) ? C11 C12 C13 C8 2.0(5) ? C9 C8 C13 O2 177.9(3) ? C7 C8 C13 O2 -4.1(5) ? C9 C8 C13 C12 -2.6(5) ? C7 C8 C13 C12 175.4(3) ? C19 C14 C15 C16 -0.2(5) ? N2 C14 C15 C16 178.5(3) ? C14 C15 C16 C17 0.8(5) ? C15 C16 C17 O4 179.2(3) ? C15 C16 C17 C18 -0.5(5) ? O4 C17 C18 C19 179.8(3) ? C16 C17 C18 C19 -0.5(5) ? C17 C18 C19 C14 1.2(5) ? C15 C14 C19 C18 -0.8(5) ? N2 C14 C19 C18 -179.6(3) ? N2 C20 C21 C22 179.8(3) ? N2 C20 C21 C26 1.4(5) yes C20 C21 C22 C23 -179.1(3) ? C26 C21 C22 C23 -0.6(5) ? C21 C22 C23 C24 1.0(6) ? C22 C23 C24 C25 -0.1(5) ? C23 C24 C25 O6 178.2(3) ? C23 C24 C25 C26 -1.2(5) ? C24 C25 C26 O5 -178.6(3) ? O6 C25 C26 O5 2.0(4) ? C24 C25 C26 C21 1.5(5) ? O6 C25 C26 C21 -177.9(3) ? C22 C21 C26 O5 179.5(3) ? C20 C21 C26 O5 -2.0(5) ? C22 C21 C26 C25 -0.6(5) ? C20 C21 C26 C25 177.9(3) ? C8 C7 N1 C1 -178.9(3) ? C2 C1 N1 C7 -13.9(5) ? C6 C1 N1 C7 167.4(3) ? C21 C20 N2 C14 -179.3(3) ? C15 C14 N2 C20 -0.5(5) ? C19 C14 N2 C20 178.2(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 12998665