#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/69/2006942.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_2006942 loop_ _publ_author_name 'Viladomat, Francesc' 'Codina, Carles' 'Bastida, Jaume' 'Solans, Xavier' 'Font-Bardia, Merc\`e' _publ_section_title ; Ismine ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 81 _journal_page_last 82 _journal_paper_doi 10.1107/S0108270197012122 _journal_volume 54 _journal_year 1998 _chemical_formula_analytical 'C15 H15 N O3' _chemical_formula_moiety 'C15 H15 N O3' _chemical_formula_structural 'C15 H15 N O3' _chemical_formula_sum 'C15 H15 N O3' _chemical_formula_weight 257.28 _chemical_name_common Ismine _chemical_name_systematic ; 6-[2-(Methylamino)phenyl]-1,3-benzodioxole-5-methanol ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method shelxl _cell_angle_alpha 102.06(3) _cell_angle_beta 103.11(2) _cell_angle_gamma 108.08(3) _cell_formula_units_Z 4 _cell_length_a 10.232(3) _cell_length_b 10.685(6) _cell_length_c 13.321(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 21 _cell_measurement_theta_min 12 _cell_volume 1285.5(10) _computing_cell_refinement 'CAD4 Software' _computing_data_collection 'CAD4 Software (Kretschmar, 1996)' _computing_data_reduction 'CFEO (Solans, 1978)' _computing_molecular_graphics 'ORTEP3.2/PC (Brueggermann & Schmid, 1990)' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'ENRAF-NONIUS CAD4' _diffrn_measurement_method \w-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 7561 _diffrn_reflns_theta_max 29.96 _diffrn_reflns_theta_min 1.65 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description prism _exptl_crystal_F_000 544 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.257 _refine_diff_density_min -0.224 _refine_ls_extinction_coef 0.017(3) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_all 0.986 _refine_ls_goodness_of_fit_obs 1.033 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 464 _refine_ls_number_reflns 7561 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0536 _refine_ls_R_factor_obs .0472 _refine_ls_shift/esd_max '0.069 (H30A)' _refine_ls_shift/esd_mean 0.007 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0892P)^2^+0.2160P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1400 _refine_ls_wR_factor_obs .1376 _reflns_number_observed 4730 _reflns_number_total 7561 _reflns_observed_criterion >2\s(I) _cod_data_source_file ln1026.cif _cod_data_source_block vid1 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' 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^)+(0.0892P)^2^+0.2160P] 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^)+(0.0892P)^2^+0.2160P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1285.5(9) _cod_database_code 2006942 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 N1A .0539(8) .0430(7) .0437(7) .0174(6) .0153(6) .0122(6) O1A .0526(8) .0910(11) .0792(9) .0177(7) .0069(7) .0394(8) O2A .0747(9) .0669(8) .0562(7) .0193(7) .0144(6) .0253(6) O3A .0502(8) .0967(13) .1092(13) .0132(8) .0353(8) .0382(11) C1A .0402(7) .0401(8) .0512(8) .0101(6) .0119(6) .0160(6) C2A .0557(10) .0562(10) .0565(10) .0114(8) .0123(8) .0257(8) C3A .0575(11) .0625(12) .093(2) .0187(9) .0100(10) .0459(12) C4A .0694(13) .0556(11) .109(2) .0331(10) .0255(12) .0351(12) C5A .0623(11) .0489(10) .0847(14) .0274(9) .0287(10) .0204(10) C6A .0424(8) .0415(8) .0553(9) .0146(6) .0170(7) .0155(7) C7A .0465(8) .0386(7) .0459(8) .0145(6) .0172(6) .0081(6) C8A .0452(8) .0497(9) .0549(9) .0118(7) .0188(7) .0162(7) C9A .0457(8) .0484(9) .0503(9) .0133(7) .0099(7) .0100(7) C10A .0717(13) .0595(12) .0640(12) .0220(10) .0064(10) .0181(10) C11A .0587(10) .0387(8) .0445(8) .0142(7) .0157(7) .0079(6) C12A .0551(10) .0473(9) .0566(10) .0130(8) .0255(8) .0146(7) C13A .0444(8) .0399(8) .0558(9) .0126(6) .0191(7) .0092(7) C14A .0443(10) .0660(13) .104(2) .0152(9) .0222(11) .0343(13) C15A .0603(11) .0620(12) .0561(11) .0198(10) .0235(9) .0094(9) N1B .0956(13) .0584(10) .0502(9) .0145(9) .0353(9) .0103(7) O1B .0471(7) .0906(10) .1006(11) .0279(7) .0347(7) .0524(9) O2B .0648(8) .0682(8) .0810(9) .0251(7) .0425(7) .0420(7) O3B .0475(7) .0752(9) .0871(10) .0066(7) -.0001(7) .0504(8) C1B .0510(9) .0571(10) .0432(8) .0218(8) .0171(7) .0227(7) C2B .0695(12) .0790(13) .0538(10) .0320(10) .0308(9) .0338(10) C3B .0697(12) .0797(14) .0778(13) .0287(11) .0385(11) .0515(12) C4B .0653(12) .0573(11) .0818(14) .0129(10) .0302(10) .0357(11) C5B .0578(10) .0479(9) .0582(10) .0139(8) .0195(8) .0215(8) C6B .0433(8) .0487(8) .0433(8) .0169(7) .0143(6) .0222(6) C7B .0426(7) .0376(7) .0371(7) .0122(6) .0134(6) .0117(6) C8B .0447(8) .0520(9) .0477(8) .0182(7) .0137(7) .0203(7) C9B .0425(8) .0456(8) .0586(9) .0162(7) .0208(7) .0165(7) C10B .0608(12) .0717(14) .104(2) .0280(11) .0458(12) .0454(13) C11B .0529(9) .0382(7) .0507(8) .0149(7) .0256(7) .0174(6) C12B .0516(9) .0475(9) .0450(8) .0130(7) .0134(7) .0209(7) C13B .0410(8) .0417(8) .0448(8) .0088(6) .0109(6) .0175(6) C14B .0405(9) .094(2) .092(2) .0122(10) .0103(10) .0642(14) C15B .109(2) .074(2) .0508(11) .0407(15) .0295(12) .0122(10) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1A -.1728(2) -.22218(14) -.00469(12) .0472(3) Uani d . 1 . N O1A .1451(2) -.0845(2) .41019(12) .0768(4) Uani d . 1 . O O2A -.0335(2) -.20482(15) .47176(11) .0678(4) Uani d . 1 . O O3A -.5334(2) -.2817(2) .2140(2) .0860(5) Uani d . 1 . O C1A -.2014(2) -.1003(2) .00929(13) .0452(3) Uani d . 1 . C C2A -.2354(2) -.0489(2) -.0778(2) .0581(4) Uani d . 1 . C C3A -.2727(2) .0668(2) -.0633(2) .0707(6) Uani d . 1 . C C4A -.2745(3) .1331(2) .0353(2) .0745(6) Uani d . 1 . C C5A -.2388(2) .0843(2) .1220(2) .0626(5) Uani d . 1 . C C6A -.2033(2) -.0327(2) .11098(13) .0462(4) Uani d . 1 . C C7A -.1660(2) -.0826(2) .20616(13) .0444(3) Uani d . 1 . C C8A -.0199(2) -.0537(2) .25919(14) .0508(4) Uani d . 1 . C C9A .0119(2) -.1000(2) .34651(13) .0509(4) Uani d . 1 . C C10A .1182(3) -.1566(2) .4865(2) .0685(5) Uani d . 1 . C C11A -.0952(2) -.1715(2) .38259(13) .0492(4) Uani d . 1 . C C12A -.2386(2) -.2014(2) .33326(15) .0534(4) Uani d . 1 . C C13A -.2751(2) -.1570(2) .24256(13) .0477(4) Uani d . 1 . C C14A -.4321(2) -.1892(3) .1818(2) .0715(6) Uani d . 1 . C C15A -.1112(2) -.2592(2) -.0887(2) .0607(5) Uani d . 1 . C N1B .2394(2) .4520(2) .49100(13) .0705(5) Uani d . 1 . N O1B -.09824(14) .4426(2) .74169(13) .0730(4) Uani d . 1 . O O2B .03482(15) .39685(15) .88417(12) .0645(4) Uani d . 1 . O O3B .5597(2) .5484(2) .89099(13) .0736(4) Uani d . 1 . O C1B .3223(2) .5901(2) .53124(13) .0484(4) Uani d . 1 . C C2B .3962(2) .6616(2) .4705(2) .0620(5) Uani d . 1 . C C3B .4795(2) .8008(2) .5129(2) .0682(6) Uani d . 1 . C C4B .4935(2) .8720(2) .6149(2) .0670(5) Uani d . 1 . C C5B .4211(2) .8031(2) .6761(2) .0550(4) Uani d . 1 . C C6B .3343(2) .6637(2) .63554(12) .0437(3) Uani d . 1 . C C7B .2588(2) .59185(15) .70393(11) .0396(3) Uani d . 1 . C C8B .1083(2) .5534(2) .68129(13) .0474(4) Uani d . 1 . C C9B .0455(2) .4880(2) .74656(14) .0480(4) Uani d . 1 . C C10B -.1085(2) .3675(3) .8180(2) .0714(6) Uani d . 1 . C C11B .1246(2) .4613(2) .83141(13) .0455(3) Uani d . 1 . C C12B .2710(2) .4973(2) .85632(13) .0486(4) Uani d . 1 . C C13B .3386(2) .5630(2) .79027(12) .0439(3) Uani d . 1 . C C14B .4986(2) .6004(3) .8105(2) .0745(7) Uani d . 1 . C C15B .2397(4) .3631(3) .3938(2) .0764(6) Uani d . 1 . C H1NA -.129(2) -.2312(19) .0576(15) .048(5) Uiso d . 1 . H H2A -.231(2) -.097(2) -.1481(18) .066(6) Uiso d . 1 . H H3A -.298(3) .096(2) -.1266(19) .076(7) Uiso d . 1 . H H4A -.298(4) .214(3) .048(2) .115(10) Uiso d . 1 . H H5A -.234(3) .134(3) .196(2) .082(7) Uiso d . 1 . H H8A .055(2) -.009(2) .2341(16) .062(6) Uiso d . 1 . H H10A .168(3) -.093(3) .562(2) .090(8) Uiso d . 1 . H H20A .143(3) -.236(3) .4701(19) .083(7) Uiso d . 1 . H H12A -.314(3) -.249(2) .3586(17) .076(6) Uiso d . 1 . H H14A -.464(3) -.243(3) .100(2) .089(8) Uiso d . 1 . H H24A -.451(4) -.109(4) .188(3) .126(11) Uiso d . 1 . H H15A -.073(3) -.325(3) -.0746(19) .079(7) Uiso d . 1 . H H25A -.034(3) -.190(3) -.095(2) .089(8) Uiso d . 1 . H H35A -.184(3) -.298(3) -.159(2) .079(7) Uiso d . 1 . H H3OA -.529(4) -.362(4) .181(3) .184(16) Uiso d . 1 . H H1NB .205(2) .420(2) .5351(17) .060(6) Uiso d . 1 . H H2B .386(2) .611(2) .3989(18) .068(6) Uiso d . 1 . H H3B .526(3) .842(2) .4658(18) .078(6) Uiso d . 1 . H H4B .553(3) .967(3) .646(2) .097(8) Uiso d . 1 . H H5B .433(2) .852(2) .7527(17) .065(6) Uiso d . 1 . H H8B .051(2) .570(2) .6211(17) .066(6) Uiso d . 1 . H H10B -.169(3) .388(3) .857(2) .086(7) Uiso d . 1 . H H20B -.151(3) .267(3) .773(2) .110(9) Uiso d . 1 . H H12B .328(2) .481(2) .9187(16) .060(5) Uiso d . 1 . H H14B .516(3) .550(3) .733(2) .100(9) Uiso d . 1 . H H24B .541(3) .698(3) .835(2) .099(9) Uiso d . 1 . H H15B .200(3) .384(3) .328(2) .103(9) Uiso d . 1 . H H25B .339(4) .371(3) .396(2) .111(10) Uiso d . 1 . H H35B .190(4) .270(4) .388(3) .125(11) Uiso d . 1 . H H3OB .651(4) .614(4) .936(3) .118(10) Uiso d . 1 . H 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 C1A N1A C15A 118.8(2) yes C1A N1A H1NA 112.4(12) no C15A N1A H1NA 112.6(12) no C9A O1A C10A 106.0(2) yes C11A O2A C10A 105.94(15) yes C14A O3A H3OA 101.(3) no C2A C1A N1A 121.2(2) yes C2A C1A C6A 119.3(2) no N1A C1A C6A 119.36(14) yes C3A C2A C1A 120.1(2) no C3A C2A H2A 122.2(13) no C1A C2A H2A 117.8(13) no C4A C3A C2A 120.9(2) no C4A C3A H3A 122.7(14) no C2A C3A H3A 116.4(14) no C3A C4A C5A 119.4(2) no C3A C4A H4A 122.8(18) no C5A C4A H4A 117.9(18) no C4A C5A C6A 121.8(2) no C4A C5A H5A 120.7(14) no C6A C5A H5A 117.5(14) no C5A C6A C1A 118.5(2) yes C5A C6A C7A 120.3(2) yes C1A C6A C7A 121.13(14) no C8A C7A C13A 120.3(2) no C8A C7A C6A 119.10(14) no C13A C7A C6A 120.58(15) no C9A C8A C7A 118.1(2) no C9A C8A H8A 119.4(12) no C7A C8A H8A 122.3(12) no C8A C9A O1A 128.4(2) no C8A C9A C11A 121.3(2) no O1A C9A C11A 110.3(2) yes O1A C10A O2A 108.1(2) yes O1A C10A H10A 110.8(15) no O2A C10A H10A 107.1(15) no O1A C10A H20A 108.0(15) no O2A C10A H20A 107.5(15) no H10A C10A H20A 115.(2) no C12A C11A C9A 122.3(2) no C12A C11A O2A 128.4(2) no C9A C11A O2A 109.4(2) yes C11A C12A C13A 117.9(2) no C11A C12A H12A 123.0(14) no C13A C12A H12A 119.1(14) no C12A C13A C7A 120.1(2) no C12A C13A C14A 121.0(2) no C7A C13A C14A 118.9(2) no O3A C14A C13A 114.5(2) no O3A C14A H14A 100.0(14) no C13A C14A H14A 114.1(15) no O3A C14A H24A 109.(2) no C13A C14A H24A 111.(2) no H14A C14A H24A 108.(3) no N1A C15A H15A 108.2(15) no N1A C15A H25A 117.7(16) no H15A C15A H25A 104.(2) no N1A C15A H35A 111.4(14) no H15A C15A H35A 109.(2) no H25A C15A H35A 106.(2) no C1B N1B C15B 123.7(2) yes C1B N1B H1NB 113.6(15) no C15B N1B H1NB 121.0(15) no C9B O1B C10B 105.52(15) yes C11B O2B C10B 104.96(15) yes C14B O3B H3OB 110.(2) no N1B C1B C6B 119.53(15) yes N1B C1B C2B 121.7(2) yes C6B C1B C2B 118.7(2) no C3B C2B C1B 120.7(2) no C3B C2B H2B 121.3(13) no C1B C2B H2B 118.0(13) no C4B C3B C2B 120.7(2) no C4B C3B H3B 123.7(14) no C2B C3B H3B 115.5(14) no C3B C4B C5B 119.3(2) no C3B C4B H4B 121.3(16) no C5B C4B H4B 119.4(16) no C6B C5B C4B 121.6(2) no C6B C5B H5B 117.6(12) no C4B C5B H5B 120.8(12) no C5B C6B C1B 118.9(2) yes C5B C6B C7B 120.37(15) yes C1B C6B C7B 120.71(14) no C13B C7B C8B 119.95(14) no C13B C7B C6B 119.96(14) no C8B C7B C6B 120.09(13) no C9B C8B C7B 117.43(15) no C9B C8B H8B 121.0(13) no C7B C8B H8B 121.6(13) no C11B C9B C8B 122.2(2) no C11B C9B O1B 109.64(14) no C8B C9B O1B 128.2(2) no O1B C10B O2B 108.1(2) yes O1B C10B H10B 110.2(15) no O2B C10B H10B 113.9(16) no O1B C10B H20B 105.1(17) no O2B C10B H20B 107.7(17) no H10B C10B H20B 111.(2) no C12B C11B C9B 122.25(14) no C12B C11B O2B 127.7(2) no C9B C11B O2B 110.01(15) yes C11B C12B C13B 117.08(15) no C11B C12B H12B 121.9(12) no C13B C12B H12B 121.0(12) no C7B C13B C12B 121.13(15) no C7B C13B C14B 119.05(14) no C12B C13B C14B 119.80(15) no O3B C14B C13B 112.1(2) no O3B C14B H14B 106.6(15) no C13B C14B H14B 108.1(15) no O3B C14B H24B 108.8(17) no C13B C14B H24B 106.1(18) no H14B C14B H24B 115.(2) no N1B C15B H15B 113.6(17) no N1B C15B H25B 111.5(18) no H15B C15B H25B 106.(2) no N1B C15B H35B 110.(2) no H15B C15B H35B 111.(3) no H25B C15B H35B 105.(3) no 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 N1A C1A . 1.405(2) yes N1A C15A . 1.448(2) yes N1A H1NA . .89(2) no O1A C9A . 1.372(2) yes O1A C10A . 1.424(3) yes O2A C11A . 1.383(2) yes O2A C10A . 1.427(3) yes O3A C14A . 1.407(3) yes O3A H3OA . .90(4) no C1A C2A . 1.404(2) no C1A C6A . 1.404(2) no C2A C3A . 1.392(3) no C2A H2A . .99(2) no C3A C4A . 1.364(4) no C3A H3A . .97(2) no C4A C5A . 1.385(3) no C4A H4A . .96(3) no C5A C6A . 1.395(3) no C5A H5A . 1.00(2) no C6A C7A . 1.492(2) yes C7A C8A . 1.404(2) no C7A C13A . 1.404(2) no C8A C9A . 1.369(2) no C8A H8A . .94(2) no C9A C11A . 1.375(2) yes C10A H10A . 1.00(3) no C10A H20A . .95(3) no C11A C12A . 1.367(3) no C12A C13A . 1.403(3) no C12A H12A . .95(2) no C13A C14A . 1.518(3) no C14A H14A . 1.04(3) no C14A H24A . .93(4) no C15A H15A . .93(3) no C15A H25A . .94(3) no C15A H35A . .97(2) no N1B C1B . 1.368(3) yes N1B C15B . 1.438(3) yes N1B H1NB . .83(2) no O1B C9B . 1.379(2) yes O1B C10B . 1.423(3) yes O2B C11B . 1.384(2) yes O2B C10B . 1.428(3) yes O3B C14B . 1.417(2) yes O3B H3OB . .94(4) no C1B C6B . 1.404(2) no C1B C2B . 1.410(2) no C2B C3B . 1.379(3) no C2B H2B . .96(2) no C3B C4B . 1.363(3) no C3B H3B . .97(2) no C4B C5B . 1.394(3) no C4B H4B . .95(3) no C5B C6B . 1.388(3) no C5B H5B . 1.00(2) no C6B C7B . 1.502(2) yes C7B C13B . 1.401(2) no C7B C8B . 1.406(2) no C8B C9B . 1.373(2) no C8B H8B . .96(2) no C9B C11B . 1.370(2) yes C10B H10B . .94(3) no C10B H20B . 1.02(3) no C11B C12B . 1.365(2) no C12B C13B . 1.407(2) no C12B H12B . .98(2) no C13B C14B . 1.504(3) no C14B H14B . 1.13(3) no C14B H24B . .94(3) no C15B H15B . .98(3) no C15B H25B . .98(3) no C15B H35B . .94(4) 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 _geom_hbond_publ_flag N1A H1NA O2B 2_556 0.889(19) 2.44(2) 3.149(3) 136.9(16) yes N1B H1NB O2A 2_556 0.83(2) 2.39(2) 3.038(3) 135.5(19) yes O3B H3OB N1A 1_666 0.94(4) 1.94(4) 2.849(3) 162(4) yes O3A H3OA O3B 2_556 0.90(4) 1.91(4) 2.799(3) 168(4) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 164188 2 PubChem 139055861