#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301802 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104945.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_2104945 loop_ _publ_author_name 'Lemmerer, Andreas' _publ_section_title ; Seven hexamethylenetetramine (HMTA) complexes with mono- and dicarboxylic acids: analysis of packing modes of HMTA complexes in the literature ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section B' _journal_page_first 177 _journal_page_last 192 _journal_paper_doi 10.1107/S0108768111004964 _journal_volume 67 _journal_year 2011 _chemical_formula_moiety 'C6 H12 N4, 2(C7 H5 F O2)' _chemical_formula_sum 'C20 H22 F2 N4 O4' _chemical_formula_weight 420.42 _chemical_name_systematic ; bis(para-flourobenzoic acid).(hexamethylenetetramine) ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 100.5530(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.15290(10) _cell_length_b 26.9424(6) _cell_length_c 11.8758(3) _cell_measurement_reflns_used 6303 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.21 _cell_measurement_theta_min 2.86 _cell_volume 1935.40(7) _computing_cell_refinement 'SAINT-Plus (Bruker, 2004)' _computing_data_collection 'APEX2 (Bruker, 2005)' _computing_data_reduction 'SAINT-Plus and XPREP (Bruker 2004)' _computing_molecular_graphics ; Ortep-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999) ; _computing_publication_material ; WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2002) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _diffrn_measurement_device_type 'Bruker APEX II CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 30806 _diffrn_reflns_theta_full 28 _diffrn_reflns_theta_max 28 _diffrn_reflns_theta_min 1.51 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.115 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.24 _refine_diff_density_max 0.215 _refine_diff_density_min -0.238 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 4670 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0379 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.6252P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.095 _refine_ls_wR_factor_ref 0.0998 _reflns_number_gt 4058 _reflns_number_total 4670 _reflns_threshold_expression >2sigma(I) _cod_data_source_file so5048.cif _cod_data_source_block 2 _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_enum 1555 2011-01-17 13:19:09Z saulius ; _cod_original_sg_symbol_H-M P2(1)/n _cod_database_code 2104945 _cod_database_fobs_code 2104945 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _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 C C1 0.54745(18) 0.25571(4) 0.51686(9) 0.0255(2) Uani d . 1 . . H H1A 0.4704 0.2617 0.4373 0.031 Uiso calc R 1 . . H H1B 0.7036 0.2476 0.5147 0.031 Uiso calc R 1 . . C C2 0.65179(19) 0.29109(5) 0.70436(10) 0.0303(2) Uani d . 1 . . H H2A 0.8093 0.2835 0.7047 0.036 Uiso calc R 1 . . H H2B 0.6453 0.3212 0.7515 0.036 Uiso calc R 1 . . C C3 0.5617(2) 0.20546(4) 0.68432(10) 0.0286(2) Uani d . 1 . . H H3A 0.4947 0.177 0.7182 0.034 Uiso calc R 1 . . H H3B 0.7183 0.1973 0.6837 0.034 Uiso calc R 1 . . C C4 0.21040(18) 0.22647(5) 0.56750(10) 0.0294(2) Uani d . 1 . . H H4A 0.1305 0.2321 0.4883 0.035 Uiso calc R 1 . . H H4B 0.1382 0.1985 0.6002 0.035 Uiso calc R 1 . . C C5 0.3029(2) 0.31203(4) 0.58638(11) 0.0302(2) Uani d . 1 . . H H5A 0.2925 0.3426 0.6315 0.036 Uiso calc R 1 . . H H5B 0.2246 0.3181 0.5071 0.036 Uiso calc R 1 . . C C6 0.3170(2) 0.26175(5) 0.75236(10) 0.0327(3) Uani d . 1 . . H H6A 0.2459 0.2339 0.7862 0.039 Uiso calc R 1 . . H H6B 0.3078 0.2915 0.8 0.039 Uiso calc R 1 . . N N1 0.44373(15) 0.21332(3) 0.56502(8) 0.02355(19) Uani d . 1 . . N N2 0.53854(16) 0.30112(4) 0.58518(8) 0.0257(2) Uani d . 1 . . N N3 0.55096(17) 0.24960(4) 0.75496(8) 0.0294(2) Uani d . 1 . . N N4 0.19563(16) 0.27115(4) 0.63584(9) 0.0300(2) Uani d . 1 . . C C7 0.70650(18) 0.09617(4) 0.32665(9) 0.0236(2) Uani d . 1 . . C C8 0.53199(18) 0.08334(4) 0.23956(10) 0.0259(2) Uani d . 1 . . H H8 0.3879 0.0956 0.2412 0.031 Uiso calc R 1 . . C C9 0.5659(2) 0.05288(4) 0.15041(10) 0.0293(2) Uani d . 1 . . H H9 0.4472 0.044 0.0908 0.035 Uiso calc R 1 . . C C10 0.7764(2) 0.03599(4) 0.15103(11) 0.0311(3) Uani d . 1 . . C C11 0.9536(2) 0.04833(5) 0.23458(12) 0.0358(3) Uani d . 1 . . H H11 1.0975 0.0362 0.2316 0.043 Uiso calc R 1 . . C C12 0.91777(19) 0.07882(4) 0.32310(11) 0.0318(3) Uani d . 1 . . H H12 1.038 0.0879 0.3817 0.038 Uiso calc R 1 . . C C13 0.67277(19) 0.12973(4) 0.42198(9) 0.0260(2) Uani d . 1 . . O O1 0.46490(14) 0.14116(3) 0.42147(7) 0.0322(2) Uani d . 1 . . H H1 0.462(3) 0.1666(8) 0.4838(18) 0.07 Uiso d . 1 . . O O2 0.82604(15) 0.14564(4) 0.49163(8) 0.0413(2) Uani d . 1 . . F F1 0.81283(14) 0.00618(3) 0.06427(7) 0.0465(2) Uani d . 1 . . C C14 0.80223(19) 0.39997(4) 0.30471(10) 0.0266(2) Uani d . 1 . . C C15 1.0190(2) 0.41335(4) 0.34873(10) 0.0283(2) Uani d . 1 . . H H15 1.0822 0.4049 0.4254 0.034 Uiso calc R 1 . . C C16 1.1439(2) 0.43886(5) 0.28192(11) 0.0337(3) Uani d . 1 . . H H16 1.2931 0.4476 0.311 0.04 Uiso calc R 1 . . C C17 1.0450(2) 0.45107(5) 0.17208(11) 0.0377(3) Uani d . 1 . . C C18 0.8302(2) 0.43930(5) 0.12611(11) 0.0401(3) Uani d . 1 . . H H18 0.7668 0.449 0.0503 0.048 Uiso calc R 1 . . C C19 0.7081(2) 0.41293(5) 0.19266(11) 0.0340(3) Uani d . 1 . . H H19 0.5602 0.4036 0.1621 0.041 Uiso calc R 1 . . C C20 0.67173(19) 0.36921(4) 0.37260(11) 0.0294(2) Uani d . 1 . . O O3 0.75605(18) 0.36740(4) 0.48286(8) 0.0443(3) Uani d . 1 . . H H3 0.674(4) 0.3467(9) 0.519(2) 0.088 Uiso d . 1 . . O O4 0.50658(16) 0.34704(4) 0.32976(9) 0.0473(3) Uani d . 1 . . F F2 1.16690(17) 0.47596(4) 0.10609(8) 0.0590(3) Uani d . 1 . . 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 0.0286(5) 0.0288(5) 0.0211(5) -0.0013(4) 0.0099(4) -0.0010(4) C2 0.0271(5) 0.0359(6) 0.0265(6) -0.0056(5) 0.0014(4) -0.0063(5) C3 0.0332(6) 0.0286(6) 0.0232(5) 0.0043(4) 0.0026(4) 0.0029(4) C4 0.0223(5) 0.0342(6) 0.0311(6) -0.0050(4) 0.0036(4) -0.0031(5) C5 0.0310(6) 0.0271(6) 0.0331(6) 0.0057(4) 0.0071(5) 0.0017(4) C6 0.0383(6) 0.0372(6) 0.0265(6) -0.0008(5) 0.0167(5) -0.0021(5) N1 0.0256(4) 0.0246(4) 0.0206(4) -0.0010(3) 0.0045(3) -0.0018(3) N2 0.0277(5) 0.0259(5) 0.0247(5) -0.0036(4) 0.0079(4) -0.0012(4) N3 0.0342(5) 0.0340(5) 0.0194(5) 0.0001(4) 0.0032(4) -0.0007(4) N4 0.0233(4) 0.0347(5) 0.0338(5) 0.0011(4) 0.0098(4) -0.0016(4) C7 0.0264(5) 0.0215(5) 0.0224(5) -0.0023(4) 0.0037(4) 0.0010(4) C8 0.0236(5) 0.0276(5) 0.0263(5) -0.0011(4) 0.0039(4) -0.0019(4) C9 0.0313(6) 0.0307(6) 0.0251(6) -0.0037(4) 0.0029(4) -0.0044(4) C10 0.0386(6) 0.0258(5) 0.0316(6) -0.0016(5) 0.0134(5) -0.0052(4) C11 0.0277(6) 0.0329(6) 0.0474(8) 0.0036(5) 0.0086(5) -0.0043(5) C12 0.0264(5) 0.0306(6) 0.0357(6) 0.0008(4) -0.0014(5) -0.0023(5) C13 0.0303(5) 0.0241(5) 0.0224(5) -0.0026(4) 0.0019(4) 0.0005(4) O1 0.0309(4) 0.0358(5) 0.0295(4) 0.0000(3) 0.0042(3) -0.0115(3) O2 0.0354(5) 0.0477(6) 0.0366(5) -0.0029(4) -0.0043(4) -0.0162(4) F1 0.0522(5) 0.0457(5) 0.0457(5) 0.0005(4) 0.0201(4) -0.0190(4) C14 0.0316(6) 0.0207(5) 0.0281(6) 0.0004(4) 0.0069(4) -0.0021(4) C15 0.0327(6) 0.0233(5) 0.0284(6) 0.0004(4) 0.0043(4) 0.0017(4) C16 0.0326(6) 0.0306(6) 0.0384(7) -0.0032(5) 0.0076(5) 0.0016(5) C17 0.0487(7) 0.0343(6) 0.0336(7) -0.0058(5) 0.0167(6) 0.0027(5) C18 0.0526(8) 0.0415(7) 0.0249(6) -0.0042(6) 0.0038(5) 0.0021(5) C19 0.0356(6) 0.0335(6) 0.0307(6) -0.0023(5) 0.0006(5) -0.0018(5) C20 0.0293(6) 0.0252(5) 0.0334(6) -0.0009(4) 0.0049(5) 0.0003(4) O3 0.0547(6) 0.0477(6) 0.0301(5) -0.0260(5) 0.0066(4) 0.0032(4) O4 0.0370(5) 0.0539(6) 0.0463(6) -0.0170(4) -0.0050(4) 0.0124(5) F2 0.0657(6) 0.0707(6) 0.0448(5) -0.0191(5) 0.0215(4) 0.0149(4) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.12 0 -1 0 0.12 0 0 1 0.25 0 0 -1 0.25 -1 -1 0 0.25 1 1 0 0.25 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N1 C1 N2 . . 111.53(8) ? N1 C1 H1A . . 109.3 ? N2 C1 H1A . . 109.3 ? N1 C1 H1B . . 109.3 ? N2 C1 H1B . . 109.3 ? H1A C1 H1B . . 108 ? N3 C2 N2 . . 111.80(9) ? N3 C2 H2A . . 109.3 ? N2 C2 H2A . . 109.3 ? N3 C2 H2B . . 109.3 ? N2 C2 H2B . . 109.3 ? H2A C2 H2B . . 107.9 ? N3 C3 N1 . . 111.45(9) ? N3 C3 H3A . . 109.3 ? N1 C3 H3A . . 109.3 ? N3 C3 H3B . . 109.3 ? N1 C3 H3B . . 109.3 ? H3A C3 H3B . . 108 ? N4 C4 N1 . . 111.45(9) ? N4 C4 H4A . . 109.3 ? N1 C4 H4A . . 109.3 ? N4 C4 H4B . . 109.3 ? N1 C4 H4B . . 109.3 ? H4A C4 H4B . . 108 ? N4 C5 N2 . . 111.66(9) ? N4 C5 H5A . . 109.3 ? N2 C5 H5A . . 109.3 ? N4 C5 H5B . . 109.3 ? N2 C5 H5B . . 109.3 ? H5A C5 H5B . . 108 ? N4 C6 N3 . . 112.64(9) ? N4 C6 H6A . . 109.1 ? N3 C6 H6A . . 109.1 ? N4 C6 H6B . . 109.1 ? N3 C6 H6B . . 109.1 ? H6A C6 H6B . . 107.8 ? C1 N1 C3 . . 108.08(9) ? C1 N1 C4 . . 108.18(9) ? C3 N1 C4 . . 108.71(9) ? C1 N2 C5 . . 107.76(9) ? C1 N2 C2 . . 108.40(9) ? C5 N2 C2 . . 108.44(9) ? C2 N3 C3 . . 108.60(9) ? C2 N3 C6 . . 107.99(9) ? C3 N3 C6 . . 108.38(9) ? C5 N4 C4 . . 108.57(9) ? C5 N4 C6 . . 108.62(9) ? C4 N4 C6 . . 107.94(10) ? C12 C7 C8 . . 119.53(10) ? C12 C7 C13 . . 119.19(10) ? C8 C7 C13 . . 121.25(10) ? C9 C8 C7 . . 120.77(10) ? C9 C8 H8 . . 119.6 ? C7 C8 H8 . . 119.6 ? C10 C9 C8 . . 117.82(11) ? C10 C9 H9 . . 121.1 ? C8 C9 H9 . . 121.1 ? F1 C10 C9 . . 118.64(11) ? F1 C10 C11 . . 118.15(11) ? C9 C10 C11 . . 123.20(11) ? C10 C11 C12 . . 118.45(11) ? C10 C11 H11 . . 120.8 ? C12 C11 H11 . . 120.8 ? C11 C12 C7 . . 120.22(11) ? C11 C12 H12 . . 119.9 ? C7 C12 H12 . . 119.9 ? O2 C13 O1 . . 123.68(11) ? O2 C13 C7 . . 122.17(11) ? O1 C13 C7 . . 114.13(9) ? C13 O1 H1 . . 107.8(11) ? C15 C14 C19 . . 119.77(11) ? C15 C14 C20 . . 121.11(10) ? C19 C14 C20 . . 119.01(11) ? C16 C15 C14 . . 120.61(11) ? C16 C15 H15 . . 119.7 ? C14 C15 H15 . . 119.7 ? C17 C16 C15 . . 117.84(12) ? C17 C16 H16 . . 121.1 ? C15 C16 H16 . . 121.1 ? F2 C17 C18 . . 118.59(12) ? F2 C17 C16 . . 118.09(12) ? C18 C17 C16 . . 123.32(12) ? C17 C18 C19 . . 118.43(12) ? C17 C18 H18 . . 120.8 ? C19 C18 H18 . . 120.8 ? C18 C19 C14 . . 120.00(12) ? C18 C19 H19 . . 120 ? C14 C19 H19 . . 120 ? O4 C20 O3 . . 123.22(12) ? O4 C20 C14 . . 122.85(11) ? O3 C20 C14 . . 113.90(10) ? C20 O3 H3 . . 109.9(15) ? 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 N1 . 1.4739(14) ? C1 N2 . 1.4746(14) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 N3 . 1.4602(15) ? C2 N2 . 1.4834(15) ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 N3 . 1.4639(15) ? C3 N1 . 1.4840(14) ? C3 H3A . 0.99 ? C3 H3B . 0.99 ? C4 N4 . 1.4639(16) ? C4 N1 . 1.4842(14) ? C4 H4A . 0.99 ? C4 H4B . 0.99 ? C5 N4 . 1.4616(15) ? C5 N2 . 1.4819(15) ? C5 H5A . 0.99 ? C5 H5B . 0.99 ? C6 N4 . 1.4691(16) ? C6 N3 . 1.4709(16) ? C6 H6A . 0.99 ? C6 H6B . 0.99 ? C7 C12 . 1.3893(16) ? C7 C8 . 1.3912(15) ? C7 C13 . 1.4928(15) ? C8 C9 . 1.3853(16) ? C8 H8 . 0.95 ? C9 C10 . 1.3714(17) ? C9 H9 . 0.95 ? C10 F1 . 1.3571(14) ? C10 C11 . 1.3740(18) ? C11 C12 . 1.3832(18) ? C11 H11 . 0.95 ? C12 H12 . 0.95 ? C13 O2 . 1.2130(14) ? C13 O1 . 1.3145(14) ? O1 H1 . 1.01(2) ? C14 C15 . 1.3880(16) ? C14 C19 . 1.3948(17) ? C14 C20 . 1.4895(16) ? C15 C16 . 1.3840(17) ? C15 H15 . 0.95 ? C16 C17 . 1.3745(19) ? C16 H16 . 0.95 ? C17 F2 . 1.3571(15) ? C17 C18 . 1.371(2) ? C18 C19 . 1.3824(19) ? C18 H18 . 0.95 ? C19 H19 . 0.95 ? C20 O4 . 1.2079(15) ? C20 O3 . 1.3181(15) ? O3 H3 . 0.91(2) ? 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 O1 H1 N1 . 1.01(2) 1.60(2) 2.6046(12) 170(2) O3 H3 N2 . 0.91(2) 1.75(2) 2.6556(13) 173(2) C2 H2A N4 1_655 0.99 2.67 3.6257(15) 162 C3 H3B O4 4_666 0.99 2.54 3.2781(15) 131 C9 H9 F1 3_655 0.95 2.59 3.5051(14) 162 C19 H19 O2 4_565 0.95 2.62 3.4148(16) 141 C2 H2A N4 1_655 0.99 2.67 3.6257(15) 161.8 C4 H4A N3 4_565 0.99 2.77 3.7176(15) 160.8 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag N2 C1 N1 C3 . . . . -58.67(11) ? N2 C1 N1 C4 . . . . 58.87(11) ? N3 C3 N1 C1 . . . . 59.24(12) ? N3 C3 N1 C4 . . . . -57.95(12) ? N4 C4 N1 C1 . . . . -58.59(12) ? N4 C4 N1 C3 . . . . 58.54(12) ? N1 C1 N2 C5 . . . . -59.03(11) ? N1 C1 N2 C2 . . . . 58.13(11) ? N4 C5 N2 C1 . . . . 59.32(12) ? N4 C5 N2 C2 . . . . -57.82(12) ? N3 C2 N2 C1 . . . . -58.18(12) ? N3 C2 N2 C5 . . . . 58.54(12) ? N2 C2 N3 C3 . . . . 58.88(12) ? N2 C2 N3 C6 . . . . -58.45(12) ? N1 C3 N3 C2 . . . . -59.43(12) ? N1 C3 N3 C6 . . . . 57.65(12) ? N4 C6 N3 C2 . . . . 58.60(12) ? N4 C6 N3 C3 . . . . -58.88(13) ? N2 C5 N4 C4 . . . . -59.57(12) ? N2 C5 N4 C6 . . . . 57.56(12) ? N1 C4 N4 C5 . . . . 59.01(12) ? N1 C4 N4 C6 . . . . -58.56(12) ? N3 C6 N4 C5 . . . . -58.35(13) ? N3 C6 N4 C4 . . . . 59.19(12) ? C12 C7 C8 C9 . . . . 1.00(17) ? C13 C7 C8 C9 . . . . 178.85(10) ? C7 C8 C9 C10 . . . . -0.08(17) ? C8 C9 C10 F1 . . . . -179.88(11) ? C8 C9 C10 C11 . . . . -0.80(19) ? F1 C10 C11 C12 . . . . 179.82(11) ? C9 C10 C11 C12 . . . . 0.7(2) ? C10 C11 C12 C7 . . . . 0.21(19) ? C8 C7 C12 C11 . . . . -1.06(18) ? C13 C7 C12 C11 . . . . -178.95(11) ? C12 C7 C13 O2 . . . . 6.02(17) ? C8 C7 C13 O2 . . . . -171.84(11) ? C12 C7 C13 O1 . . . . -175.55(10) ? C8 C7 C13 O1 . . . . 6.59(15) ? C19 C14 C15 C16 . . . . -0.92(17) ? C20 C14 C15 C16 . . . . 175.28(11) ? C14 C15 C16 C17 . . . . 1.11(18) ? C15 C16 C17 F2 . . . . -179.83(12) ? C15 C16 C17 C18 . . . . 0.1(2) ? F2 C17 C18 C19 . . . . 178.50(12) ? C16 C17 C18 C19 . . . . -1.4(2) ? C17 C18 C19 C14 . . . . 1.6(2) ? C15 C14 C19 C18 . . . . -0.45(18) ? C20 C14 C19 C18 . . . . -176.72(12) ? C15 C14 C20 O4 . . . . -161.74(12) ? C19 C14 C20 O4 . . . . 14.49(18) ? C15 C14 C20 O3 . . . . 16.59(16) ? C19 C14 C20 O3 . . . . -167.18(11) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 30654558 2 PubChem 139064034