#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104946.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_2104946 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_volume 67 _journal_year 2011 _chemical_formula_moiety 'C6 H12 N4, 2(C8 H8 O2)' _chemical_formula_sum 'C22 H28 N4 O4' _chemical_formula_weight 412.48 _chemical_name_systematic ; bis(toluidine carboxylic 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 99.869(15) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.1754(18) _cell_length_b 28.234(7) _cell_length_c 12.154(3) _cell_measurement_reflns_used 1336 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.37 _cell_measurement_theta_min 2.89 _cell_volume 2087.8(10) _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 0.993 _diffrn_measured_fraction_theta_max 0.993 _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 0.0935 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 10621 _diffrn_reflns_theta_full 25.5 _diffrn_reflns_theta_max 25.5 _diffrn_reflns_theta_min 1.44 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.866 _refine_diff_density_min -0.548 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 3866 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.1952 _refine_ls_R_factor_gt 0.1209 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3241 _refine_ls_wR_factor_ref 0.3664 _reflns_number_gt 1948 _reflns_number_total 3866 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file so5048.cif _[local]_cod_data_source_block 3 _[local]_cod_cif_authors_sg_H-M P2(1)/n _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_cell_volume 2087.8(9) _cod_database_code 2104946 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 0.2161(10) 0.24714(18) 0.3143(5) 0.0270(14) Uani d . 1 . . H H1A 0.1433 0.2406 0.2367 0.032 Uiso calc R 1 . . H H1B 0.3727 0.2542 0.3132 0.032 Uiso calc R 1 . . C C2 0.2197(11) 0.2974(2) 0.4740(5) 0.0368(16) Uani d . 1 . . H H2A 0.3763 0.3054 0.4754 0.044 Uiso calc R 1 . . H H2B 0.1489 0.3249 0.5042 0.044 Uiso calc R 1 . . C C3 0.3083(10) 0.2154(2) 0.5004(5) 0.0354(16) Uani d . 1 . . H H3A 0.2976 0.1873 0.548 0.043 Uiso calc R 1 . . H H3B 0.466 0.2222 0.5017 0.043 Uiso calc R 1 . . C C4 -0.0332(10) 0.1951(2) 0.3839(6) 0.0385(17) Uani d . 1 . . H H4A -0.0464 0.1668 0.4303 0.046 Uiso calc R 1 . . H H4B -0.1067 0.1881 0.3067 0.046 Uiso calc R 1 . . C C5 -0.1218(10) 0.2767(2) 0.3581(6) 0.0382(16) Uani d . 1 . . H H5A -0.1954 0.3041 0.3866 0.046 Uiso calc R 1 . . H H5B -0.1962 0.2704 0.2806 0.046 Uiso calc R 1 . . C C6 -0.0306(11) 0.2459(2) 0.5401(5) 0.0385(17) Uani d . 1 . . H H6A -0.0465 0.2186 0.5893 0.046 Uiso calc R 1 . . H H6B -0.1012 0.2736 0.5692 0.046 Uiso calc R 1 . . N N1 0.1998(8) 0.20508(17) 0.3841(4) 0.0300(13) Uani d . 1 . . N N2 0.1119(8) 0.28861(16) 0.3574(4) 0.0274(12) Uani d . 1 . . N N3 0.2045(9) 0.25591(18) 0.5448(4) 0.0381(14) Uani d . 1 . . N N4 -0.1441(8) 0.2353(2) 0.4273(5) 0.0386(14) Uani d . 1 . . C C7 0.3988(10) 0.1078(2) 0.1016(5) 0.0292(14) Uani d . 1 . . C C8 0.6121(10) 0.0933(2) 0.1299(5) 0.0367(16) Uani d . 1 . . H H8 0.6937 0.1007 0.2014 0.044 Uiso calc R 1 . . C C9 0.7099(11) 0.0674(2) 0.0535(6) 0.0417(18) Uani d . 1 . . H H9 0.858 0.0571 0.0731 0.05 Uiso calc R 1 . . C C10 0.5912(12) 0.0568(2) -0.0506(5) 0.0394(17) Uani d . 1 . . C C11 0.3783(13) 0.0722(2) -0.0789(5) 0.0424(18) Uani d . 1 . . H H11 0.2979 0.0652 -0.151 0.051 Uiso calc R 1 . . C C12 0.2792(12) 0.0976(2) -0.0040(5) 0.0379(16) Uani d . 1 . . H H12 0.1314 0.1081 -0.0241 0.046 Uiso calc R 1 . . C C13 0.2881(10) 0.1372(2) 0.1787(5) 0.0299(14) Uani d . 1 . . C C14 0.6969(13) 0.0287(3) -0.1324(6) 0.056(2) Uani d . 1 . . H H14A 0.6828 -0.0052 -0.1178 0.084 Uiso calc R 1 . . H H14B 0.8528 0.0371 -0.124 0.084 Uiso calc R 1 . . H H14C 0.6237 0.036 -0.2086 0.084 Uiso calc R 1 . . O O1 0.4019(8) 0.14065(16) 0.2790(4) 0.0491(14) Uani d . 1 . . H H1 0.3327 0.1573 0.3186 0.074 Uiso calc R 1 . . O O2 0.1130(8) 0.15501(19) 0.1498(4) 0.0580(16) Uani d . 1 . . C C15 0.3948(10) 0.39169(19) 0.1124(5) 0.0254(13) Uani d . 1 . . C C16 0.2243(10) 0.4037(2) 0.0250(5) 0.0342(15) Uani d . 1 . . H H16 0.0783 0.3937 0.0273 0.041 Uiso calc R 1 . . C C17 0.2680(11) 0.4301(2) -0.0641(5) 0.0383(16) Uani d . 1 . . H H17 0.1517 0.4385 -0.1226 0.046 Uiso calc R 1 . . C C18 0.4779(11) 0.4441(2) -0.0685(5) 0.0333(15) Uani d . 1 . . C C19 0.6460(11) 0.4325(2) 0.0167(6) 0.0410(18) Uani d . 1 . . H H19 0.7917 0.4426 0.0136 0.049 Uiso calc R 1 . . C C20 0.6034(10) 0.4055(2) 0.1092(6) 0.0364(16) Uani d . 1 . . H H20 0.7195 0.3972 0.1679 0.044 Uiso calc R 1 . . C C21 0.3455(10) 0.3621(2) 0.2084(5) 0.0299(14) Uani d . 1 . . C C22 0.5325(13) 0.4718(2) -0.1665(6) 0.051(2) Uani d . 1 . . H H22A 0.6338 0.4976 -0.1391 0.076 Uiso calc R 1 . . H H22B 0.3974 0.485 -0.2095 0.076 Uiso calc R 1 . . H H22C 0.6019 0.4507 -0.2143 0.076 Uiso calc R 1 . . O O3 0.1429(7) 0.35404(15) 0.2081(4) 0.0418(12) Uani d . 1 . . H H3 0.1291 0.3375 0.2639 0.063 Uiso calc R 1 . . O O4 0.4955(8) 0.34793(17) 0.2798(4) 0.0521(14) 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 0.039(4) 0.023(3) 0.022(3) 0.001(3) 0.015(3) 0.003(2) C2 0.051(4) 0.033(4) 0.029(4) -0.009(3) 0.014(3) -0.004(3) C3 0.033(3) 0.043(4) 0.030(4) 0.010(3) 0.005(3) 0.003(3) C4 0.038(4) 0.036(4) 0.044(4) -0.007(3) 0.015(3) -0.009(3) C5 0.039(4) 0.035(4) 0.043(4) 0.009(3) 0.013(3) 0.004(3) C6 0.061(5) 0.032(4) 0.031(4) -0.001(3) 0.031(4) 0.000(3) N1 0.038(3) 0.027(3) 0.028(3) 0.000(2) 0.013(2) 0.002(2) N2 0.038(3) 0.022(3) 0.024(3) 0.003(2) 0.013(2) -0.002(2) N3 0.049(3) 0.041(3) 0.026(3) 0.000(3) 0.010(3) 0.000(2) N4 0.036(3) 0.040(3) 0.043(3) 0.002(2) 0.016(3) 0.002(3) C7 0.045(4) 0.019(3) 0.028(3) -0.001(3) 0.018(3) 0.003(2) C8 0.041(4) 0.034(4) 0.036(4) 0.005(3) 0.009(3) -0.001(3) C9 0.040(4) 0.031(4) 0.059(5) 0.010(3) 0.023(4) 0.003(3) C10 0.066(5) 0.025(3) 0.034(4) 0.002(3) 0.028(4) 0.007(3) C11 0.068(5) 0.033(4) 0.029(4) -0.002(3) 0.016(4) -0.001(3) C12 0.053(4) 0.027(3) 0.037(4) 0.004(3) 0.017(3) 0.002(3) C13 0.034(4) 0.018(3) 0.037(4) 0.001(3) 0.006(3) 0.000(3) C14 0.091(6) 0.040(4) 0.049(5) 0.006(4) 0.042(5) -0.004(3) O1 0.062(3) 0.046(3) 0.038(3) 0.025(2) 0.004(3) -0.011(2) O2 0.041(3) 0.075(4) 0.054(3) 0.023(3) -0.003(3) -0.028(3) C15 0.035(3) 0.018(3) 0.025(3) 0.005(2) 0.011(3) 0.000(2) C16 0.035(4) 0.021(3) 0.047(4) -0.001(3) 0.007(3) -0.001(3) C17 0.046(4) 0.032(4) 0.033(4) 0.005(3) -0.005(3) 0.000(3) C18 0.042(4) 0.029(3) 0.032(4) 0.007(3) 0.016(3) -0.005(3) C19 0.031(4) 0.025(4) 0.073(5) -0.003(3) 0.024(4) -0.009(3) C20 0.029(3) 0.033(4) 0.044(4) 0.002(3) -0.002(3) -0.002(3) C21 0.033(3) 0.016(3) 0.039(4) 0.004(3) 0.000(3) -0.002(3) C22 0.084(6) 0.032(4) 0.044(4) -0.006(4) 0.034(4) 0.001(3) O3 0.035(3) 0.040(3) 0.051(3) 0.000(2) 0.009(2) 0.012(2) O4 0.051(3) 0.053(3) 0.048(3) -0.006(2) -0.002(3) 0.021(2) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 0 0.03 0 1 0 0.02 1 0 1 0.15 -1 0 -1 0.09 -1 0 2 0.18 1 0 -2 0.14 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 . . 111.0(4) ? N1 C1 H1A . . 109.4 ? N2 C1 H1A . . 109.4 ? N1 C1 H1B . . 109.4 ? N2 C1 H1B . . 109.4 ? H1A C1 H1B . . 108 ? N3 C2 N2 . . 111.3(5) ? N3 C2 H2A . . 109.4 ? N2 C2 H2A . . 109.4 ? N3 C2 H2B . . 109.4 ? N2 C2 H2B . . 109.4 ? H2A C2 H2B . . 108 ? N3 C3 N1 . . 110.5(5) ? N3 C3 H3A . . 109.6 ? N1 C3 H3A . . 109.6 ? N3 C3 H3B . . 109.6 ? N1 C3 H3B . . 109.6 ? H3A C3 H3B . . 108.1 ? N1 C4 N4 . . 111.7(5) ? N1 C4 H4A . . 109.3 ? N4 C4 H4A . . 109.3 ? N1 C4 H4B . . 109.3 ? N4 C4 H4B . . 109.3 ? H4A C4 H4B . . 107.9 ? N4 C5 N2 . . 111.9(5) ? N4 C5 H5A . . 109.2 ? N2 C5 H5A . . 109.2 ? N4 C5 H5B . . 109.2 ? N2 C5 H5B . . 109.2 ? H5A C5 H5B . . 107.9 ? N4 C6 N3 . . 112.8(4) ? N4 C6 H6A . . 109 ? N3 C6 H6A . . 109 ? N4 C6 H6B . . 109 ? N3 C6 H6B . . 109 ? H6A C6 H6B . . 107.8 ? C4 N1 C1 . . 108.5(5) ? C4 N1 C3 . . 108.8(4) ? C1 N1 C3 . . 109.0(5) ? C1 N2 C2 . . 108.8(5) ? C1 N2 C5 . . 107.8(4) ? C2 N2 C5 . . 108.2(4) ? C3 N3 C2 . . 109.5(5) ? C3 N3 C6 . . 109.2(5) ? C2 N3 C6 . . 107.1(5) ? C6 N4 C5 . . 107.5(5) ? C6 N4 C4 . . 108.5(5) ? C5 N4 C4 . . 108.3(5) ? C8 C7 C12 . . 120.3(6) ? C8 C7 C13 . . 122.1(6) ? C12 C7 C13 . . 117.5(6) ? C7 C8 C9 . . 119.8(7) ? C7 C8 H8 . . 120.1 ? C9 C8 H8 . . 120.1 ? C10 C9 C8 . . 120.0(6) ? C10 C9 H9 . . 120 ? C8 C9 H9 . . 120 ? C11 C10 C9 . . 119.8(6) ? C11 C10 C14 . . 120.4(7) ? C9 C10 C14 . . 119.8(7) ? C10 C11 C12 . . 120.8(7) ? C10 C11 H11 . . 119.6 ? C12 C11 H11 . . 119.6 ? C11 C12 C7 . . 119.2(6) ? C11 C12 H12 . . 120.4 ? C7 C12 H12 . . 120.4 ? O2 C13 O1 . . 124.1(6) ? O2 C13 C7 . . 122.6(6) ? O1 C13 C7 . . 113.3(5) ? C10 C14 H14A . . 109.5 ? C10 C14 H14B . . 109.5 ? H14A C14 H14B . . 109.5 ? C10 C14 H14C . . 109.5 ? H14A C14 H14C . . 109.5 ? H14B C14 H14C . . 109.5 ? C13 O1 H1 . . 109.5 ? C20 C15 C16 . . 120.2(5) ? C20 C15 C21 . . 120.1(6) ? C16 C15 C21 . . 119.7(5) ? C17 C16 C15 . . 120.2(6) ? C17 C16 H16 . . 119.9 ? C15 C16 H16 . . 119.9 ? C18 C17 C16 . . 120.2(6) ? C18 C17 H17 . . 119.9 ? C16 C17 H17 . . 119.9 ? C17 C18 C19 . . 120.1(6) ? C17 C18 C22 . . 121.5(6) ? C19 C18 C22 . . 118.4(6) ? C18 C19 C20 . . 120.4(6) ? C18 C19 H19 . . 119.8 ? C20 C19 H19 . . 119.8 ? C15 C20 C19 . . 118.9(6) ? C15 C20 H20 . . 120.5 ? C19 C20 H20 . . 120.5 ? O4 C21 O3 . . 124.7(6) ? O4 C21 C15 . . 120.1(6) ? O3 C21 C15 . . 115.2(5) ? C18 C22 H22A . . 109.5 ? C18 C22 H22B . . 109.5 ? H22A C22 H22B . . 109.5 ? C18 C22 H22C . . 109.5 ? H22A C22 H22C . . 109.5 ? H22B C22 H22C . . 109.5 ? C21 O3 H3 . . 109.5 ? 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 . 1.473(7) ? C1 N2 . 1.475(7) ? C1 H1A . 0.99 ? C1 H1B . 0.99 ? C2 N3 . 1.467(8) ? C2 N2 . 1.480(8) ? C2 H2A . 0.99 ? C2 H2B . 0.99 ? C3 N3 . 1.460(8) ? C3 N1 . 1.486(8) ? C3 H3A . 0.99 ? C3 H3B . 0.99 ? C4 N1 . 1.466(7) ? C4 N4 . 1.469(8) ? C4 H4A . 0.99 ? C4 H4B . 0.99 ? C5 N4 . 1.460(8) ? C5 N2 . 1.483(8) ? C5 H5A . 0.99 ? C5 H5B . 0.99 ? C6 N4 . 1.460(8) ? C6 N3 . 1.471(8) ? C6 H6A . 0.99 ? C6 H6B . 0.99 ? C7 C8 . 1.367(9) ? C7 C12 . 1.396(9) ? C7 C13 . 1.500(8) ? C8 C9 . 1.397(8) ? C8 H8 . 0.95 ? C9 C10 . 1.383(10) ? C9 H9 . 0.95 ? C10 C11 . 1.371(10) ? C10 C14 . 1.505(8) ? C11 C12 . 1.383(8) ? C11 H11 . 0.95 ? C12 H12 . 0.95 ? C13 O2 . 1.190(7) ? C13 O1 . 1.302(7) ? C14 H14A . 0.98 ? C14 H14B . 0.98 ? C14 H14C . 0.98 ? O1 H1 . 0.84 ? C15 C20 . 1.352(8) ? C15 C16 . 1.403(8) ? C15 C21 . 1.508(8) ? C16 C17 . 1.378(9) ? C16 H16 . 0.95 ? C17 C18 . 1.365(9) ? C17 H17 . 0.95 ? C18 C19 . 1.374(9) ? C18 C22 . 1.510(8) ? C19 C20 . 1.420(9) ? C19 H19 . 0.95 ? C20 H20 . 0.95 ? C21 O4 . 1.223(7) ? C21 O3 . 1.271(7) ? C22 H22A . 0.98 ? C22 H22B . 0.98 ? C22 H22C . 0.98 ? O3 H3 . 0.84 ? 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 . 0.84 1.83 2.654(6) 166 O3 H3 N2 . 0.84 1.8 2.620(6) 164 C1 H1A O2 . 0.99 2.63 3.276(7) 123 C2 H2A O2 4_666 0.99 2.61 3.239(8) 121 C3 H3B N4 1_655 0.99 2.74 3.684(8) 160 C4 H4B O2 . 0.99 2.69 3.327(8) 123 C5 H5B N3 4_565 0.99 2.92 3.885(9) 164 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 N4 C4 N1 C1 . . . . -59.2(6) ? N4 C4 N1 C3 . . . . 59.3(7) ? N2 C1 N1 C4 . . . . 59.5(6) ? N2 C1 N1 C3 . . . . -58.8(6) ? N3 C3 N1 C4 . . . . -59.2(6) ? N3 C3 N1 C1 . . . . 59.0(6) ? N1 C1 N2 C2 . . . . 58.1(6) ? N1 C1 N2 C5 . . . . -59.0(6) ? N3 C2 N2 C1 . . . . -58.0(6) ? N3 C2 N2 C5 . . . . 58.9(6) ? N4 C5 N2 C1 . . . . 59.1(6) ? N4 C5 N2 C2 . . . . -58.4(6) ? N1 C3 N3 C2 . . . . -59.0(6) ? N1 C3 N3 C6 . . . . 57.9(6) ? N2 C2 N3 C3 . . . . 58.9(7) ? N2 C2 N3 C6 . . . . -59.3(6) ? N4 C6 N3 C3 . . . . -57.9(6) ? N4 C6 N3 C2 . . . . 60.6(6) ? N3 C6 N4 C5 . . . . -60.1(6) ? N3 C6 N4 C4 . . . . 56.9(6) ? N2 C5 N4 C6 . . . . 58.3(6) ? N2 C5 N4 C4 . . . . -58.7(7) ? N1 C4 N4 C6 . . . . -57.7(6) ? N1 C4 N4 C5 . . . . 58.7(7) ? C12 C7 C8 C9 . . . . -1.0(9) ? C13 C7 C8 C9 . . . . -177.7(5) ? C7 C8 C9 C10 . . . . 0.3(9) ? C8 C9 C10 C11 . . . . 0.7(9) ? C8 C9 C10 C14 . . . . -179.7(6) ? C9 C10 C11 C12 . . . . -0.9(9) ? C14 C10 C11 C12 . . . . 179.4(6) ? C10 C11 C12 C7 . . . . 0.2(9) ? C8 C7 C12 C11 . . . . 0.8(9) ? C13 C7 C12 C11 . . . . 177.6(5) ? C8 C7 C13 O2 . . . . 170.2(6) ? C12 C7 C13 O2 . . . . -6.5(9) ? C8 C7 C13 O1 . . . . -10.2(8) ? C12 C7 C13 O1 . . . . 173.0(5) ? C20 C15 C16 C17 . . . . -0.6(9) ? C21 C15 C16 C17 . . . . -178.9(5) ? C15 C16 C17 C18 . . . . 0.8(9) ? C16 C17 C18 C19 . . . . -0.8(9) ? C16 C17 C18 C22 . . . . 178.2(5) ? C17 C18 C19 C20 . . . . 0.6(9) ? C22 C18 C19 C20 . . . . -178.5(5) ? C16 C15 C20 C19 . . . . 0.4(9) ? C21 C15 C20 C19 . . . . 178.7(5) ? C18 C19 C20 C15 . . . . -0.4(9) ? C20 C15 C21 O4 . . . . -4.7(9) ? C16 C15 C21 O4 . . . . 173.6(6) ? C20 C15 C21 O3 . . . . 174.8(5) ? C16 C15 C21 O3 . . . . -6.9(8) ? _cod_database_fobs_code 2104946