#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200547.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_2200547 loop_ _publ_author_name 'Dupont, L\'eon' 'Khelili, Smail' 'Pirotte, Bernard' 'Tinant, Bernard' 'de Tullio, Pascal' _publ_section_title ;Absolute configuration of N-[(R)-3-methyl-2-butyl]-(S)-2-(6-methoxy-2-naphthyl)propionamide ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o650 _journal_page_last o651 _journal_paper_doi 10.1107/S1600536801010285 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C19 H25 N O2' _chemical_formula_moiety 'C19 H25 N O2' _chemical_formula_sum 'C19 H25 N O2' _chemical_formula_weight 299.40 _chemical_name_systematic ; N-[(R)-3-methyl-2-butyl]-(S)-2-(6-methoxy-2-naphthyl)propionamide ; _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 99.11(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.879(2) _cell_length_b 29.563(9) _cell_length_c 8.511(3) _cell_measurement_reflns_used 133 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.5 _cell_measurement_theta_min 2.5 _cell_volume 1709.0(9) _computing_cell_refinement 'marHKL (Klein & Bartels, 2000)' _computing_data_reduction 'marHKL (Klein & Bartels, 2000)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.66 _diffrn_measured_fraction_theta_full .987 _diffrn_measured_fraction_theta_max .987 _diffrn_measurement_device_type 'MAR345 image-plate' _diffrn_measurement_method '222 images, 150mm, \D\F 2\%' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .056 _diffrn_reflns_av_sigmaI/netI .0541 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 19313 _diffrn_reflns_theta_full 24.41 _diffrn_reflns_theta_max 24.41 _diffrn_reflns_theta_min 2.79 _exptl_absorpt_coefficient_mu .075 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.164 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 648 _exptl_crystal_size_max .34 _exptl_crystal_size_mid .23 _exptl_crystal_size_min .23 _refine_diff_density_max .233 _refine_diff_density_min -.204 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -.3(12) _refine_ls_extinction_coef .171(12) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 414 _refine_ls_number_reflns 5448 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all .0571 _refine_ls_R_factor_gt .0531 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1033P)^2^+0.0697P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1495 _reflns_number_gt 4896 _reflns_number_total 5448 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6026.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2200547 _cod_database_fobs_code 2200547 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' 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 C1A .8795(5) .29334(14) -.1585(5) .1109(12) Uani d . 1 . . C H1A .8928 .2687 -.2297 .166 Uiso calc R 1 . . H H2A .9727 .2897 -.0627 .166 Uiso calc R 1 . . H H3A .9041 .3214 -.2085 .166 Uiso calc R 1 . . H C2A .6323(4) .32952(10) -.0339(4) .0745(7) Uani d . 1 . . C C3A .7437(4) .36648(9) .0083(3) .0701(7) Uani d . 1 . . C H4A .8683 .3689 -.0202 .084 Uiso calc R 1 . . H C4A .6700(3) .40182(8) .0966(3) .0602(6) Uani d . 1 . . C C5A .7811(4) .44039(8) .1465(4) .0686(7) Uani d . 1 . . C H5A .9092 .4428 .1252 .082 Uiso calc R 1 . . H C6A .7054(3) .47402(8) .2247(3) .0647(6) Uani d . 1 . . C H6A .7832 .4992 .2559 .078 Uiso calc R 1 . . H C7A .5091(3) .47253(7) .2618(3) .0542(5) Uani d . 1 . . C C8A .4036(3) .43429(8) .2198(3) .0603(6) Uani d . 1 . . C H7A .2776 .4318 .2456 .072 Uiso calc R 1 . . H C9A .4796(3) .39770(8) .1373(3) .0584(5) Uani d . 1 . . C C10A .3681(4) .35861(9) .0933(4) .0753(7) Uani d . 1 . . C H8A .2432 .3556 .1208 .090 Uiso calc R 1 . . H C11A .4427(4) .32486(10) .0100(4) .0833(8) Uani d . 1 . . C H9A .3690 .2989 -.0178 .100 Uiso calc R 1 . . H C12A .4351(3) .51331(7) .3417(3) .0525(5) Uani d . 1 . . C H10A .5196 .5177 .4446 .063 Uiso calc R 1 . . H C13A .2219(4) .50999(10) .3707(4) .0720(7) Uani d . 1 . . C H11A .1909 .5358 .4304 .108 Uiso calc R 1 . . H H12A .2054 .4829 .4295 .108 Uiso calc R 1 . . H H13A .1354 .5091 .2705 .108 Uiso calc R 1 . . H C14A .4558(3) .55512(7) .2372(2) .0493(5) Uani d . 1 . . C C15A .6693(4) .62180(9) .2099(3) .0652(6) Uani d . 1 . . C H14A .5949 .6220 .1018 .078 Uiso calc R 1 . . H C16A .8890(4) .61429(12) .1984(4) .0835(8) Uani d . 1 . . C H15A .9310 .6366 .1289 .125 Uiso calc R 1 . . H H16A .9062 .5846 .1569 .125 Uiso calc R 1 . . H H17A .9662 .6170 .3023 .125 Uiso calc R 1 . . H C17A .6288(5) .66553(10) .2901(4) .0791(8) Uani d . 1 . . C H18A .6953 .6644 .4008 .095 Uiso calc R 1 . . H C18A .4108(5) .67128(12) .2905(4) .0937(9) Uani d . 1 . . C H19A .3900 .6947 .3643 .141 Uiso calc R 1 . . H H20A .3566 .6434 .3218 .141 Uiso calc R 1 . . H H21A .3471 .6794 .1857 .141 Uiso calc R 1 . . H C19A .7125(9) .70641(13) .2068(7) .146(2) Uani d . 1 . . C H22A .7822 .6955 .1251 .219 Uiso calc R 1 . . H H23A .8008 .7233 .2837 .219 Uiso calc R 1 . . H H24A .6061 .7256 .1602 .219 Uiso calc R 1 . . H N1A .6015(3) .58300(7) .2959(2) .0600(5) Uani d . 1 . . N H25A .674(4) .5749(9) .399(3) .072 Uiso d . 1 . . H O1A .6865(3) .29359(8) -.1209(3) .0926(6) Uani d . 1 . . O O2A .3479(2) .56055(6) .10909(18) .0638(4) Uani d . 1 . . O C1B 1.4133(5) .28841(11) .4488(5) .0954(10) Uani d . 1 . . C H1B 1.4852 .3128 .4108 .143 Uiso calc R 1 . . H H2B 1.4403 .2609 .3964 .143 Uiso calc R 1 . . H H3B 1.4529 .2851 .5615 .143 Uiso calc R 1 . . H C2B 1.1441(4) .33587(8) .4836(3) .0624(6) Uani d . 1 . . C C3B 1.2575(3) .36409(8) .5873(3) .0612(6) Uani d . 1 . . C H4B 1.3906 .3578 .6180 .073 Uiso calc R 1 . . H C4B 1.1744(3) .40273(7) .6484(3) .0548(5) Uani d . 1 . . C C5B 1.2848(3) .43316(8) .7546(3) .0630(6) Uani d . 1 . . C H5B 1.4183 .4278 .7871 .076 Uiso calc R 1 . . H C6B 1.2012(3) .47019(7) .8109(3) .0578(6) Uani d . 1 . . C H6B 1.2784 .4892 .8821 .069 Uiso calc R 1 . . H C7B .9991(3) .48051(7) .7637(3) .0497(5) Uani d . 1 . . C C8B .8885(3) .45100(7) .6601(3) .0525(5) Uani d . 1 . . C H7B .7554 .4570 .6281 .063 Uiso calc R 1 . . H C9B .9706(3) .41237(7) .6015(3) .0518(5) Uani d . 1 . . C C10B .8583(3) .38165(8) .4936(3) .0628(6) Uani d . 1 . . C H8B .7245 .3870 .4619 .075 Uiso calc R 1 . . H C11B .9417(4) .34519(8) .4366(3) .0664(6) Uani d . 1 . . C H9B .8652 .3259 .3656 .080 Uiso calc R 1 . . H C12B .9178(3) .52326(7) .8281(3) .0517(5) Uani d . 1 . . C H10B .9860 .5280 .9369 .062 Uiso calc R 1 . . H C13B .6956(3) .52122(9) .8328(3) .0636(6) Uani d . 1 . . C H11B .6568 .5475 .8865 .095 Uiso calc R 1 . . H H12B .6663 .4945 .8888 .095 Uiso calc R 1 . . H H13B .6249 .5204 .7262 .095 Uiso calc R 1 . . H C14B .9612(3) .56364(7) .7280(2) .0497(5) Uani d . 1 . . C C15B 1.1743(3) .63025(8) .7141(3) .0586(6) Uani d . 1 . . C H14B 1.1059 .6309 .6040 .070 Uiso calc R 1 . . H C16B 1.3948(4) .62548(13) .7123(5) .0938(10) Uani d . 1 . . C H15B 1.4360 .6479 .6428 .141 Uiso calc R 1 . . H H16B 1.4220 .5959 .6750 .141 Uiso calc R 1 . . H H17B 1.4652 .6297 .8180 .141 Uiso calc R 1 . . H C17B 1.1237(5) .67353(10) .7980(4) .0821(8) Uani d . 1 . . C H18B 1.1815 .6712 .9106 .098 Uiso calc R 1 . . H C18B .9055(5) .67922(13) .7879(5) .1041(11) Uani d . 1 . . C H19B .8790 .7043 .8531 .156 Uiso calc R 1 . . H H20B .8501 .6522 .8247 .156 Uiso calc R 1 . . H H21B .8477 .6849 .6795 .156 Uiso calc R 1 . . H C19B 1.2091(9) .71554(14) .7288(8) .154(2) Uani d . 1 . . C H22B 1.3500 .7133 .7436 .232 Uiso calc R 1 . . H H23B 1.1720 .7420 .7822 .232 Uiso calc R 1 . . H H24B 1.1587 .7177 .6172 .232 Uiso calc R 1 . . H N1B 1.1086(3) .59047(7) .7934(2) .0571(5) Uani d . 1 . . N H25B 1.181(4) .5859(10) .901(3) .069 Uiso d . 1 . . H O1B 1.2087(3) .29784(6) .4159(3) .0818(6) Uani d . 1 . . O O2B .8661(2) .57009(6) .59501(19) .0678(5) 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 C1A .102(2) .096(2) .141(3) .0166(19) .040(2) -.026(2) C2A .0831(18) .0627(15) .0750(16) .0152(13) .0040(13) -.0093(13) C3A .0661(15) .0690(16) .0719(15) .0096(12) .0004(12) .0032(13) C4A .0557(12) .0604(13) .0622(13) .0013(10) .0024(11) .0086(11) C5A .0528(12) .0613(15) .0912(18) -.0034(10) .0104(12) .0056(13) C6A .0541(12) .0568(13) .0828(17) -.0010(10) .0095(12) .0047(12) C7A .0526(12) .0531(12) .0523(11) -.0008(9) -.0060(10) .0100(9) C8A .0551(12) .0609(13) .0628(13) -.0030(10) .0033(10) .0006(10) C9A .0519(12) .0584(12) .0608(13) -.0036(10) -.0031(10) .0057(10) C10A .0630(13) .0676(16) .0964(19) -.0113(12) .0161(13) -.0088(14) C11A .0782(17) .0692(16) .102(2) -.0086(14) .0118(16) -.0149(16) C12A .0539(11) .0543(12) .0466(11) -.0011(9) -.0003(9) .0056(9) C13A .0644(14) .0712(16) .0836(18) -.0001(12) .0216(13) .0053(13) C14A .0510(10) .0512(11) .0430(10) -.0011(9) -.0014(9) .0001(9) C15A .0773(15) .0624(14) .0532(13) -.0123(11) .0021(11) .0047(11) C16A .0720(17) .093(2) .089(2) .0003(14) .0225(15) .0143(16) C17A .097(2) .0628(16) .0795(18) -.0071(14) .0197(16) .0009(13) C18A .098(2) .091(2) .094(2) .0227(17) .0226(18) -.0009(17) C19A .207(5) .066(2) .188(5) -.030(3) .102(4) -.003(3) N1A .0698(12) .0565(11) .0477(10) -.0121(8) -.0087(9) .0075(8) O1A .0889(13) .0792(13) .1099(16) .0081(10) .0166(12) -.0271(12) O2A .0665(9) .0660(10) .0516(9) -.0051(7) -.0133(7) .0052(7) C1B .090(2) .080(2) .119(3) .0225(16) .0235(19) -.0139(18) C2B .0693(14) .0507(13) .0682(14) .0009(11) .0143(12) -.0027(11) C3B .0554(12) .0552(13) .0726(14) .0032(10) .0085(11) .0032(11) C4B .0544(12) .0496(12) .0580(12) .0011(9) .0018(10) .0063(9) C5B .0478(11) .0650(14) .0714(14) .0005(10) -.0058(10) -.0020(11) C6B .0520(12) .0547(13) .0617(13) -.0021(10) -.0067(10) -.0037(10) C7B .0524(11) .0494(11) .0443(10) .0008(9) -.0022(9) .0040(8) C8B .0474(10) .0497(12) .0569(13) -.0018(8) -.0018(9) .0008(9) C9B .0508(11) .0472(11) .0545(12) -.0043(9) -.0002(9) .0025(9) C10B .0581(12) .0560(13) .0703(15) -.0016(10) -.0024(11) -.0058(10) C11B .0691(14) .0555(13) .0705(15) -.0037(11) -.0009(12) -.0097(11) C12B .0564(12) .0526(12) .0439(11) .0017(9) .0012(9) .0017(9) C13B .0601(13) .0700(15) .0611(14) .0027(11) .0113(11) -.0018(11) C14B .0548(11) .0494(11) .0422(10) .0040(9) -.0007(9) .0004(9) C15B .0559(12) .0592(13) .0581(13) -.0056(10) .0010(10) .0106(10) C16B .0634(16) .118(3) .101(2) .0088(15) .0161(16) .031(2) C17B .0913(19) .0650(16) .091(2) -.0090(14) .0195(16) .0063(14) C18B .105(2) .098(2) .116(3) .0285(19) .038(2) .009(2) C19B .180(5) .073(2) .230(6) -.023(3) .095(5) .011(3) N1B .0612(11) .0544(11) .0515(11) -.0049(8) -.0044(9) .0073(8) O1B .0772(12) .0615(11) .1081(16) .0038(9) .0194(11) -.0196(10) O2B .0766(10) .0682(11) .0503(9) -.0081(8) -.0156(8) .0074(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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 .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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 O1A C1A H1A 109.5 no O1A C1A H2A 109.5 no H1A C1A H2A 109.5 no O1A C1A H3A 109.5 no H1A C1A H3A 109.5 no H2A C1A H3A 109.5 no C3A C2A O1A 125.1(3) no C3A C2A C11A 121.0(2) no O1A C2A C11A 113.9(3) no C2A C3A C4A 119.9(2) no C2A C3A H4A 120.0 no C4A C3A H4A 120.0 no C5A C4A C9A 118.6(2) no C5A C4A C3A 122.2(2) no C9A C4A C3A 119.1(2) no C6A C5A C4A 121.0(2) no C6A C5A H5A 119.5 no C4A C5A H5A 119.5 no C5A C6A C7A 122.5(2) no C5A C6A H6A 118.8 no C7A C6A H6A 118.8 no C8A C7A C6A 116.7(2) no C8A C7A C12A 125.3(2) no C6A C7A C12A 118.04(19) no C7A C8A C9A 122.3(2) no C7A C8A H7A 118.8 no C9A C8A H7A 118.8 no C10A C9A C4A 119.6(2) no C10A C9A C8A 121.7(2) no C4A C9A C8A 118.7(2) no C11A C10A C9A 120.2(2) no C11A C10A H8A 119.9 no C9A C10A H8A 119.9 no C10A C11A C2A 120.0(3) no C10A C11A H9A 120.0 no C2A C11A H9A 120.0 no C7A C12A C13A 114.94(19) no C7A C12A C14A 108.13(16) no C13A C12A C14A 108.85(18) no C7A C12A H10A 108.2 no C13A C12A H10A 108.2 no C14A C12A H10A 108.2 no C12A C13A H11A 109.5 no C12A C13A H12A 109.5 no H11A C13A H12A 109.5 no C12A C13A H13A 109.5 no H11A C13A H13A 109.5 no H12A C13A H13A 109.5 no O2A C14A N1A 124.4(2) yes O2A C14A C12A 121.23(18) yes N1A C14A C12A 114.33(18) yes N1A C15A C17A 110.3(2) no N1A C15A C16A 108.0(2) no C17A C15A C16A 113.8(2) no N1A C15A H14A 108.2 no C17A C15A H14A 108.2 no C16A C15A H14A 108.2 no C15A C16A H15A 109.5 no C15A C16A H16A 109.5 no H15A C16A H16A 109.5 no C15A C16A H17A 109.5 no H15A C16A H17A 109.5 no H16A C16A H17A 109.5 no C15A C17A C18A 110.6(3) no C15A C17A C19A 110.6(3) no C18A C17A C19A 110.6(3) no C15A C17A H18A 108.3 no C18A C17A H18A 108.3 no C19A C17A H18A 108.3 no C17A C18A H19A 109.5 no C17A C18A H20A 109.5 no H19A C18A H20A 109.5 no C17A C18A H21A 109.5 no H19A C18A H21A 109.5 no H20A C18A H21A 109.5 no C17A C19A H22A 109.5 no C17A C19A H23A 109.5 no H22A C19A H23A 109.5 no C17A C19A H24A 109.5 no H22A C19A H24A 109.5 no H23A C19A H24A 109.5 no C14A N1A C15A 124.98(19) no C14A N1A H25A 115.8(16) no C15A N1A H25A 119.0(16) no C2A O1A C1A 118.0(3) yes O1B C1B H1B 109.5 no O1B C1B H2B 109.5 no H1B C1B H2B 109.5 no O1B C1B H3B 109.5 no H1B C1B H3B 109.5 no H2B C1B H3B 109.5 no C3B C2B O1B 125.7(2) no C3B C2B C11B 120.0(2) no O1B C2B C11B 114.3(2) no C2B C3B C4B 120.5(2) no C2B C3B H4B 119.7 no C4B C3B H4B 119.7 no C5B C4B C3B 122.9(2) no C5B C4B C9B 117.3(2) no C3B C4B C9B 119.8(2) no C6B C5B C4B 121.7(2) no C6B C5B H5B 119.2 no C4B C5B H5B 119.2 no C5B C6B C7B 121.6(2) no C5B C6B H6B 119.2 no C7B C6B H6B 119.2 no C8B C7B C6B 117.48(19) no C8B C7B C12B 123.98(19) no C6B C7B C12B 118.53(19) no C7B C8B C9B 122.02(19) no C7B C8B H7B 119.0 no C9B C8B H7B 119.0 no C8B C9B C4B 119.88(19) no C8B C9B C10B 122.65(19) no C4B C9B C10B 117.5(2) no C11B C10B C9B 121.5(2) no C11B C10B H8B 119.3 no C9B C10B H8B 119.3 no C10B C11B C2B 120.7(2) no C10B C11B H9B 119.6 no C2B C11B H9B 119.6 no C7B C12B C14B 109.53(16) no C7B C12B C13B 113.68(19) no C14B C12B C13B 109.24(18) no C7B C12B H10B 108.1 no C14B C12B H10B 108.1 no C13B C12B H10B 108.1 no C12B C13B H11B 109.5 no C12B C13B H12B 109.5 no H11B C13B H12B 109.5 no C12B C13B H13B 109.5 no H11B C13B H13B 109.5 no H12B C13B H13B 109.5 no O2B C14B N1B 123.3(2) yes O2B C14B C12B 120.89(18) yes N1B C14B C12B 115.77(18) yes N1B C15B C16B 108.1(2) no N1B C15B C17B 110.27(19) no C16B C15B C17B 112.4(2) no N1B C15B H14B 108.7 no C16B C15B H14B 108.7 no C17B C15B H14B 108.7 no C15B C16B H15B 109.5 no C15B C16B H16B 109.5 no H15B C16B H16B 109.5 no C15B C16B H17B 109.5 no H15B C16B H17B 109.5 no H16B C16B H17B 109.5 no C18B C17B C19B 109.2(3) no C18B C17B C15B 111.5(3) no C19B C17B C15B 111.6(3) no C18B C17B H18B 108.1 no C19B C17B H18B 108.1 no C15B C17B H18B 108.1 no C17B C18B H19B 109.5 no C17B C18B H20B 109.5 no H19B C18B H20B 109.5 no C17B C18B H21B 109.5 no H19B C18B H21B 109.5 no H20B C18B H21B 109.5 no C17B C19B H22B 109.5 no C17B C19B H23B 109.5 no H22B C19B H23B 109.5 no C17B C19B H24B 109.5 no H22B C19B H24B 109.5 no H23B C19B H24B 109.5 no C14B N1B C15B 123.64(19) no C14B N1B H25B 123.2(16) no C15B N1B H25B 113.2(16) no C2B O1B C1B 117.2(2) yes 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 C1A O1A . 1.414(4) yes C1A H1A . .9600 no C1A H2A . .9600 no C1A H3A . .9600 no C2A C3A . 1.350(4) no C2A O1A . 1.380(3) yes C2A C11A . 1.419(4) no C3A C4A . 1.426(4) no C3A H4A . .9300 no C4A C5A . 1.401(4) no C4A C9A . 1.411(3) no C5A C6A . 1.346(4) no C5A H5A . .9300 no C6A C7A . 1.435(3) no C6A H6A . .9300 no C7A C8A . 1.360(3) no C7A C12A . 1.511(3) no C8A C9A . 1.433(3) no C8A H7A . .9300 no C9A C10A . 1.405(3) no C10A C11A . 1.370(4) no C10A H8A . .9300 no C11A H9A . .9300 no C12A C13A . 1.529(3) no C12A C14A . 1.543(3) no C12A H10A . .9800 no C13A H11A . .9600 no C13A H12A . .9600 no C13A H13A . .9600 no C14A O2A . 1.228(3) yes C14A N1A . 1.332(3) yes C15A N1A . 1.475(3) yes C15A C17A . 1.508(4) no C15A C16A . 1.546(4) no C15A H14A . .9800 no C16A H15A . .9600 no C16A H16A . .9600 no C16A H17A . .9600 no C17A C18A . 1.510(4) no C17A C19A . 1.557(5) no C17A H18A . .9800 no C18A H19A . .9600 no C18A H20A . .9600 no C18A H21A . .9600 no C19A H22A . .9600 no C19A H23A . .9600 no C19A H24A . .9600 no N1A H25A . .97(3) no C1B O1B . 1.418(3) yes C1B H1B . .9600 no C1B H2B . .9600 no C1B H3B . .9600 no C2B C3B . 1.366(3) no C2B O1B . 1.369(3) yes C2B C11B . 1.414(3) no C3B C4B . 1.413(3) no C3B H4B . .9300 no C4B C5B . 1.409(3) no C4B C9B . 1.424(3) no C5B C6B . 1.359(3) no C5B H5B . .9300 no C6B C7B . 1.417(3) no C6B H6B . .9300 no C7B C8B . 1.381(3) no C7B C12B . 1.519(3) no C8B C9B . 1.400(3) no C8B H7B . .9300 no C9B C10B . 1.429(3) no C10B C11B . 1.347(3) no C10B H8B . .9300 no C11B H9B . .9300 no C12B C14B . 1.523(3) no C12B C13B . 1.537(3) no C12B H10B . .9800 no C13B H11B . .9600 no C13B H12B . .9600 no C13B H13B . .9600 no C14B O2B . 1.229(3) yes C14B N1B . 1.337(3) yes C15B N1B . 1.463(3) yes C15B C16B . 1.526(4) no C15B C17B . 1.532(4) no C15B H14B . .9800 no C16B H15B . .9600 no C16B H16B . .9600 no C16B H17B . .9600 no C17B C18B . 1.499(5) no C17B C19B . 1.531(5) no C17B H18B . .9800 no C18B H19B . .9600 no C18B H20B . .9600 no C18B H21B . .9600 no C19B H22B . .9600 no C19B H23B . .9600 no C19B H24B . .9600 no N1B H25B . .98(3) no 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 N1A H25A O2B . .97(3) 1.96(3) 2.911(3) 166(2) N1B H25B O2A 1_656 .98(3) 2.09(3) 3.051(3) 166(2) 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 O1A C2A C3A C4A 179.0(2) no C11A C2A C3A C4A -.8(4) no C2A C3A C4A C5A 178.5(3) no C2A C3A C4A C9A -.7(4) no C9A C4A C5A C6A -3.3(4) no C3A C4A C5A C6A 177.6(2) no C4A C5A C6A C7A .1(4) no C5A C6A C7A C8A 2.7(3) no C5A C6A C7A C12A -176.6(2) no C6A C7A C8A C9A -2.3(3) no C12A C7A C8A C9A 176.9(2) no C5A C4A C9A C10A -177.8(3) no C3A C4A C9A C10A 1.4(3) no C5A C4A C9A C8A 3.5(3) no C3A C4A C9A C8A -177.3(2) no C7A C8A C9A C10A -179.4(3) no C7A C8A C9A C4A -.7(3) no C4A C9A C10A C11A -.7(4) no C8A C9A C10A C11A 177.9(3) no C9A C10A C11A C2A -.8(5) no C3A C2A C11A C10A 1.5(5) no O1A C2A C11A C10A -178.3(3) no C8A C7A C12A C13A -1.7(3) no C6A C7A C12A C13A 177.4(2) no C8A C7A C12A C14A -123.6(2) no C6A C7A C12A C14A 55.6(2) no C7A C12A C14A O2A 71.6(2) yes C13A C12A C14A O2A -53.9(3) no C7A C12A C14A N1A -106.6(2) yes C13A C12A C14A N1A 127.9(2) no N1A C15A C17A C18A -60.8(3) no C16A C15A C17A C18A 177.6(3) no N1A C15A C17A C19A 176.2(3) no C16A C15A C17A C19A 54.7(4) no O2A C14A N1A C15A -6.8(4) no C12A C14A N1A C15A 171.3(2) yes C17A C15A N1A C14A 114.6(3) yes C16A C15A N1A C14A -120.5(3) yes C3A C2A O1A C1A 5.5(5) yes C11A C2A O1A C1A -174.7(3) no O1B C2B C3B C4B 179.3(2) no C11B C2B C3B C4B .0(4) no C2B C3B C4B C5B -179.5(2) no C2B C3B C4B C9B .0(3) no C3B C4B C5B C6B 179.7(2) no C9B C4B C5B C6B .2(4) no C4B C5B C6B C7B -1.0(4) no C5B C6B C7B C8B 1.1(3) no C5B C6B C7B C12B -178.2(2) no C6B C7B C8B C9B -.5(3) no C12B C7B C8B C9B 178.81(19) no C7B C8B C9B C4B -.3(3) no C7B C8B C9B C10B -179.7(2) no C5B C4B C9B C8B .4(3) no C3B C4B C9B C8B -179.1(2) no C5B C4B C9B C10B 179.9(2) no C3B C4B C9B C10B .4(3) no C8B C9B C10B C11B 178.7(2) no C4B C9B C10B C11B -.7(4) no C9B C10B C11B C2B .7(4) no C3B C2B C11B C10B -.3(4) no O1B C2B C11B C10B -179.8(2) no C8B C7B C12B C14B -96.5(2) no C6B C7B C12B C14B 82.8(2) no C8B C7B C12B C13B 26.0(3) no C6B C7B C12B C13B -154.6(2) no C7B C12B C14B O2B 75.6(2) yes C13B C12B C14B O2B -49.5(3) no C7B C12B C14B N1B -103.6(2) yes C13B C12B C14B N1B 131.2(2) no N1B C15B C17B C18B -63.5(3) no C16B C15B C17B C18B 175.8(3) no N1B C15B C17B C19B 174.1(3) no C16B C15B C17B C19B 53.4(4) no O2B C14B N1B C15B -.5(3) no C12B C14B N1B C15B 178.7(2) yes C16B C15B N1B C14B -125.4(3) yes C17B C15B N1B C14B 111.4(3) yes C3B C2B O1B C1B -4.0(4) yes C11B C2B O1B C1B 175.5(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 24731181 2 PubChem 139064947