#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/06/2200671.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_2200671 loop_ _publ_author_name 'Justin Robert, Jebamony' 'Baskar Raj, Savarimuthu' 'Thomas Muthiah, Packianathan' _publ_section_title ; N---H···O and O---H···O hydrogen bonds in crystal engineering: trimethoprim hydrogen glutarate ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1206 _journal_page_last o1208 _journal_paper_doi 10.1107/S1600536801018001 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C14 H19 N4 O3 1+, C5 H7 O4 1-' _chemical_formula_moiety 'C14 H19 N4 O3 1+, C5 H7 O4 1-' _chemical_formula_sum 'C19 H26 N4 O7' _chemical_formula_weight 422.44 _chemical_name_common 'trimethoprim glutarate' _chemical_name_systematic ; 2,4-diamino-5-(3,4,5-trimethoxybenzyl)pyrimidin-1-ium glutarate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 84.430(3) _cell_angle_beta 94.900(3) _cell_angle_gamma 104.590(3) _cell_formula_units_Z 2 _cell_length_a 12.017(2) _cell_length_b 10.090(3) _cell_length_c 8.804(4) _cell_measurement_reflns_used 40 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.9 _cell_measurement_theta_min 3.8 _cell_volume 1026.1(6) _computing_cell_refinement MolEN _computing_data_collection 'MolEN (Fair, 1990)' _computing_data_reduction MolEN _computing_molecular_graphics 'ORTEPII (Johnson, 1997) and PLATON (Spek, 1997)' _computing_publication_material PLATON _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 290 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0160 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3203 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_max 70.90 _diffrn_reflns_theta_min 3.81 _diffrn_standards_decay_% negligible _diffrn_standards_interval_time 100 _diffrn_standards_number 1 _exptl_absorpt_coefficient_mu .886 _exptl_absorpt_correction_type none _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_meas ? _exptl_crystal_description 'thin plate' _exptl_crystal_F_000 448 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .22 _exptl_crystal_size_min .19 _refine_diff_density_max .212 _refine_diff_density_min -.227 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 363 _refine_ls_number_reflns 3203 _refine_ls_restrained_S_all 1.113 _refine_ls_restrained_S_obs 1.095 _refine_ls_R_factor_all .048 _refine_ls_R_factor_gt .048 _refine_ls_shift/esd_mean .000 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0866P)^2^+0.1793P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .1402 _refine_ls_wR_factor_ref .1401 _reflns_number_gt 3201 _reflns_number_total 3203 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file cv6070.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_refine_ls_weighting_scheme' value 'calc ' changed to 'calc' 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_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_database_code 2200671 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 O1 .0623(9) .0730(9) .0425(7) .0242(7) -.0178(6) -.0137(6) O2 .0463(8) .0617(8) .0632(9) .0194(6) -.0184(6) -.0057(7) O3 .0579(8) .0791(10) .0521(8) .0335(7) -.0016(7) -.0095(7) N1 .0559(10) .0568(9) .0362(8) .0191(8) -.0087(7) -.0075(7) N2 .0778(12) .0601(10) .0335(8) .0206(9) -.0137(8) -.0041(7) N3 .0618(10) .0559(9) .0368(8) .0224(8) -.0123(7) -.0060(7) N4 .0913(14) .0665(11) .0453(9) .0185(10) -.0269(9) -.0106(8) C2 .0529(10) .0565(11) .0346(9) .0259(9) -.0067(7) -.0062(8) C4 .0531(10) .0624(11) .0363(9) .0256(9) -.0111(8) -.0091(8) C5 .0447(10) .0671(12) .0344(9) .0264(9) -.0048(7) -.0015(8) C6 .0487(10) .0601(11) .0380(9) .0215(9) -.0031(8) .0009(8) C7 .0475(11) .0916(16) .0351(10) .0294(10) -.0042(8) .0037(9) C8 .0441(9) .0540(10) .0318(8) .0150(8) -.0049(7) .0054(7) C9 .0473(10) .0534(10) .0363(9) .0182(8) -.0022(7) .0003(7) C10 .0480(10) .0441(9) .0370(9) .0099(8) -.0096(7) -.0002(7) C11 .0411(9) .0447(9) .0460(10) .0120(8) -.0097(8) .0014(8) C12 .0455(10) .0442(9) .0441(10) .0145(8) .0001(8) .0013(7) C13 .0473(10) .0536(10) .0337(9) .0154(8) -.0054(7) -.0002(7) C14 .0773(15) .0705(14) .0450(11) .0219(12) -.0100(10) -.0156(10) C15 .0932(19) .0690(16) .105(2) .0394(14) -.0495(17) -.0099(14) C16 .0840(17) .0896(17) .0559(13) .0452(14) .0034(12) -.0126(12) O4 .0981(13) .0656(10) .0387(7) -.0026(9) -.0159(8) -.0004(7) O5 .0904(12) .0756(10) .0283(7) .0067(8) -.0054(7) -.0004(6) O6 .0981(13) .1065(14) .0543(9) .0601(12) -.0022(9) -.0001(9) O7 .1041(13) .0958(13) .0474(9) .0590(11) .0186(9) .0171(8) C17 .0562(11) .0426(9) .0386(9) .0085(8) -.0055(8) -.0076(7) C18 .0796(15) .0553(12) .0394(10) .0083(10) .0014(10) -.0017(8) C19 .0742(14) .0598(12) .0357(10) .0023(10) -.0059(9) -.0030(8) C20 .0698(14) .0612(12) .0377(10) .0083(10) -.0001(9) -.0026(9) C21 .0522(11) .0654(12) .0319(9) .0075(9) .0003(8) -.0012(8) 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_type_symbol O1 .45141(13) .87527(15) .73650(15) .0585(5) Uani . . 1.000 O O2 .59069(12) .78210(15) .57704(17) .0572(5) Uani . . 1.000 O O3 .52998(13) .71564(16) .29046(16) .0600(5) Uani . . 1.000 O N1 .05252(14) .82591(17) -.10391(17) .0491(5) Uani . . 1.000 N N2 .06864(17) .98838(19) -.31074(18) .0575(6) Uani . . 1.000 N N3 .15813(15) 1.05315(17) -.07878(18) .0508(5) Uani . . 1.000 N N4 .24980(19) 1.1136(2) .1481(2) .0693(7) Uani . . 1.000 N C2 .09384(17) .9571(2) -.1627(2) .0461(6) Uani . . 1.000 C C4 .18378(17) 1.0157(2) .0689(2) .0490(6) Uani . . 1.000 C C5 .14042(16) .8791(2) .1401(2) .0471(6) Uani . . 1.000 C C6 .07496(17) .7889(2) .0470(2) .0481(6) Uani . . 1.000 C C7 .15670(17) .8417(3) .3090(2) .0568(7) Uani . . 1.000 C C8 .27701(15) .83263(19) .37225(19) .0438(5) Uani . . 1.000 C C9 .30932(16) .86674(19) .5205(2) .0452(6) Uani . . 1.000 C C10 .41372(16) .84784(18) .5896(2) .0442(5) Uani . . 1.000 C C11 .48561(15) .79685(18) .5096(2) .0447(5) Uani . . 1.000 C C12 .45284(16) .76436(19) .3595(2) .0445(6) Uani . . 1.000 C C13 .34798(16) .78229(19) .2912(2) .0450(6) Uani . . 1.000 C C14 .3789(2) .9274(3) .8200(2) .0637(8) Uani . . 1.000 C C15 .5871(3) .6471(3) .6435(4) .0887(11) Uani . . 1.000 C C16 .5029(2) .6836(3) .1364(3) .0718(9) Uani . . 1.000 C O4 .07782(16) .22219(17) .46913(16) .0730(6) Uani . . 1.000 O O5 .08143(15) .37575(17) .27020(15) .0680(6) Uani . . 1.000 O O6 .27767(17) .4052(2) 1.00442(19) .0808(7) Uani . . 1.000 O O7 .14593(17) .5178(2) 1.01426(18) .0769(7) Uani . . 1.000 O C17 .21973(17) .47756(18) .9423(2) .0467(6) Uani . . 1.000 C C18 .2212(2) .5289(2) .7757(2) .0599(7) Uani . . 1.000 C C19 .1775(2) .4110(2) .6763(2) .0597(7) Uani . . 1.000 C C20 .1615(2) .4566(2) .5084(2) .0579(7) Uani . . 1.000 C C21 .10397(17) .3416(2) .4102(2) .0514(6) Uani . . 1.000 C H1 .01188 .76561 -.16215 .0589 Uiso . . 1.000 H H2A .09426 1.07055 -.35075 .0690 Uiso . . 1.000 H H2B .02682 .92626 -.36587 .0690 Uiso . . 1.000 H H4A .27354 1.19502 .10514 .0831 Uiso . . 1.000 H H4B .26913 1.09607 .24285 .0831 Uiso . . 1.000 H H6 .04414 .69920 .08567 .0578 Uiso . . 1.000 H H7A .10386 .75354 .33305 .0682 Uiso . . 1.000 H H7B .13408 .90891 .36339 .0682 Uiso . . 1.000 H H9 .26158 .90228 .57429 .0542 Uiso . . 1.000 H H13 .32619 .76023 .19099 .0540 Uiso . . 1.000 H H14A .36428 1.00926 .76587 .0955 Uiso . . 1.000 H H14B .41563 .94859 .91885 .0955 Uiso . . 1.000 H H14C .30728 .85986 .83196 .0955 Uiso . . 1.000 H H15A .53305 .62400 .72187 .1328 Uiso . . 1.000 H H15B .66225 .64316 .68745 .1328 Uiso . . 1.000 H H15C .56371 .58310 .56618 .1328 Uiso . . 1.000 H H16A .43188 .61417 .12954 .1077 Uiso . . 1.000 H H16B .56356 .65035 .10126 .1077 Uiso . . 1.000 H H16C .49499 .76465 .07415 .1077 Uiso . . 1.000 H H7 .13895 .47592 1.09892 .1155 Uiso . . 1.000 H H18A .17318 .59359 .75535 .0719 Uiso . . 1.000 H H18B .29921 .57640 .75171 .0719 Uiso . . 1.000 H H19A .10431 .35621 .71116 .0717 Uiso . . 1.000 H H19B .23141 .35296 .68798 .0717 Uiso . . 1.000 H H20A .11585 .52405 .49846 .0695 Uiso . . 1.000 H H20B .23641 .50118 .47063 .0695 Uiso . . 1.000 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 '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' C C .0181 .0091 '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 C10 O1 C14 116.40(16) yes C11 O2 C15 113.33(19) yes C12 O3 C16 117.51(17) yes C17 O7 H7 109.42 no C2 N1 C6 120.61(16) yes C2 N3 C4 117.39(17) yes C2 N1 H1 119.68 no C6 N1 H1 119.71 no C2 N2 H2A 120.02 no H2A N2 H2B 120.00 no C2 N2 H2B 119.97 no H4A N4 H4B 119.99 no C4 N4 H4B 119.98 no C4 N4 H4A 120.03 no N2 C2 N3 119.60(18) yes N1 C2 N3 122.10(16) yes N1 C2 N2 118.30(17) yes N3 C4 C5 123.49(17) yes N3 C4 N4 115.62(18) yes N4 C4 C5 120.87(17) yes C4 C5 C6 114.99(16) no C6 C5 C7 121.26(19) no C4 C5 C7 123.50(18) no N1 C6 C5 121.36(18) yes C5 C7 C8 117.48(17) no C7 C8 C13 122.08(16) no C9 C8 C13 120.37(17) no C7 C8 C9 117.35(17) no C8 C9 C10 119.93(17) no O1 C10 C11 115.66(17) yes C9 C10 C11 120.26(16) no O1 C10 C9 124.08(17) yes C10 C11 C12 119.34(17) no O2 C11 C10 120.07(16) yes O2 C11 C12 120.57(17) yes O3 C12 C11 114.75(17) yes O3 C12 C13 125.00(16) yes C11 C12 C13 120.26(17) no C8 C13 C12 119.83(16) no C5 C6 H6 119.36 no N1 C6 H6 119.28 no C5 C7 H7A 107.96 no C5 C7 H7B 107.95 no C8 C7 H7B 107.92 no H7A C7 H7B 107.19 no C8 C7 H7A 107.91 no C10 C9 H9 120.02 no C8 C9 H9 120.05 no C12 C13 H13 120.08 no C8 C13 H13 120.09 no O1 C14 H14A 109.48 no O1 C14 H14B 109.53 no H14A C14 H14B 109.47 no H14A C14 H14C 109.40 no O1 C14 H14C 109.48 no H14B C14 H14C 109.47 no O2 C15 H15B 109.43 no O2 C15 H15C 109.49 no O2 C15 H15A 109.46 no H15A C15 H15C 109.53 no H15B C15 H15C 109.48 no H15A C15 H15B 109.45 no O3 C16 H16B 109.43 no O3 C16 H16C 109.44 no H16A C16 H16B 109.51 no H16A C16 H16C 109.51 no H16B C16 H16C 109.49 no O3 C16 H16A 109.45 no O6 C17 O7 121.99(18) yes O6 C17 C18 125.14(19) yes O7 C17 C18 112.85(18) yes C17 C18 C19 110.45(15) no C18 C19 C20 113.27(16) no C19 C20 C21 114.01(16) no O4 C21 C20 119.42(16) yes O5 C21 C20 116.42(17) yes O4 C21 O5 124.11(18) yes C17 C18 H18A 109.55 no C17 C18 H18B 109.54 no C19 C18 H18A 109.58 no C19 C18 H18B 109.57 no H18A C18 H18B 108.12 no C18 C19 H19A 108.93 no C18 C19 H19B 108.94 no C20 C19 H19A 108.91 no C20 C19 H19B 108.94 no H19A C19 H19B 107.70 no C19 C20 H20A 108.74 no C19 C20 H20B 108.71 no C21 C20 H20A 108.79 no C21 C20 H20B 108.75 no H20A C20 H20B 107.66 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C10 . . 1.364(2) yes O1 C14 . . 1.411(3) yes O2 C11 . . 1.385(2) yes O2 C15 . . 1.421(3) yes O3 C12 . . 1.362(3) yes O3 C16 . . 1.417(3) yes O4 C21 . . 1.239(3) yes O5 C21 . . 1.272(2) yes O6 C17 . . 1.196(3) yes O7 C17 . . 1.296(3) yes O7 H7 . . .8203 no N1 C6 . . 1.368(2) yes N1 C2 . . 1.359(3) yes N2 C2 . . 1.338(2) yes N3 C2 . . 1.321(3) yes N3 C4 . . 1.350(2) yes N4 C4 . . 1.317(3) yes N1 H1 . . .8600 no N2 H2B . . .8601 no N2 H2A . . .8599 no N4 H4B . . .8603 no N4 H4A . . .8599 no C4 C5 . . 1.446(3) no C5 C7 . . 1.507(3) no C5 C6 . . 1.339(3) no C7 C8 . . 1.526(3) no C8 C9 . . 1.381(3) no C8 C13 . . 1.374(3) no C9 C10 . . 1.396(3) no C10 C11 . . 1.380(3) no C11 C12 . . 1.392(3) no C12 C13 . . 1.395(3) no C6 H6 . . .9301 no C7 H7B . . .9702 no C7 H7A . . .9701 no C9 H9 . . .9301 no C13 H13 . . .9305 no C14 H14B . . .9596 no C14 H14A . . .9605 no C14 H14C . . .9604 no C15 H15B . . .9603 no C15 H15C . . .9595 no C15 H15A . . .9599 no C16 H16B . . .9600 no C16 H16A . . .9597 no C16 H16C . . .9599 no C17 C18 . . 1.507(3) no C18 C19 . . 1.505(3) no C19 C20 . . 1.516(3) no C20 C21 . . 1.503(3) no C18 H18A . . .9698 no C18 H18B . . .9700 no C19 H19A . . .9704 no C19 H19B . . .9702 no C20 H20A . . .9696 no C20 H20B . . .9702 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O2 2.666(2) . no O1 C15 3.334(4) . no O2 O1 2.666(2) . no O2 O3 2.667(2) . no O2 N4 3.053(3) 2_676 no O3 O2 2.667(2) . no O3 C15 3.173(4) . no O4 N2 2.890(3) 1_546 no O4 N2 2.798(3) 2_565 no O5 N1 2.720(3) 2_565 no O5 C17 3.396(3) 1_554 no O5 O7 2.616(3) 1_554 no O6 C16 3.355(4) 2_666 no O6 N4 3.037(3) 1_546 no O7 O5 2.616(3) 1_556 no O7 C6 3.109(3) 1_556 no O2 H4B 2.3962 2_676 no O3 H15C 2.7056 . no O3 H14A 2.7620 2_676 no O4 H19B 2.7421 . no O4 H19A 2.5879 . no O4 H2B 1.9420 2_565 no O4 H1 2.8259 2_565 no O4 H2A 2.1266 1_546 no O5 H7 1.8175 1_554 no O5 H1 1.8633 2_565 no O6 H16A 2.6883 1_556 no O6 H15B 2.7757 2_667 no O6 H19B 2.8673 . no O6 H4A 2.2081 1_546 no O6 H16B 2.4007 2_666 no O7 H6 2.8803 2_566 no O7 H6 2.5931 1_556 no N1 O5 2.720(3) 2_565 no N2 O4 2.798(3) 2_565 no N2 O4 2.890(3) 1_564 no N3 C14 3.430(3) 1_554 no N4 O6 3.037(3) 1_564 no N4 C8 3.363(3) . no N4 O2 3.053(3) 2_676 no N4 C15 3.301(4) 2_676 no N2 H7B 2.8652 2_575 no N4 H7B 2.8347 . no N4 H15B 2.8911 2_676 no C2 C14 3.530(4) 1_554 no C2 C4 3.587(3) 2_575 no C4 C2 3.587(3) 2_575 no C6 O7 3.109(3) 1_554 no C8 N4 3.363(3) . no C10 C11 3.531(3) 2_676 no C10 C10 3.554(3) 2_676 no C11 C10 3.531(3) 2_676 no C12 C14 3.561(4) 2_676 no C14 C12 3.561(4) 2_676 no C14 C2 3.530(4) 1_556 no C14 N3 3.430(3) 1_556 no C15 O3 3.173(4) . no C15 O1 3.334(4) . no C15 N4 3.301(4) 2_676 no C16 O6 3.355(4) 2_666 no C17 O5 3.396(3) 1_556 no C2 H14C 2.9734 1_554 no C5 H13 2.7743 . no C7 H4B 2.6171 . no C8 H4B 2.8094 . no C9 H14A 2.6555 . no C9 H14C 2.7383 . no C10 H18B 3.0182 . no C10 H15A 3.0577 . no C12 H15C 2.9323 . no C12 H14A 2.9430 2_676 no C13 H16C 2.7578 . no C13 H16A 2.7377 . no C14 H16C 3.0914 1_556 no C14 H9 2.4773 . no C15 H4A 2.9911 2_676 no C15 H4B 2.9418 2_676 no C16 H13 2.5322 . no C17 H16A 3.0116 1_556 no C21 H15B 2.9706 2_666 no C21 H7 2.9517 1_554 no C21 H1 2.6567 2_565 no C21 H2B 2.8084 2_565 no H1 O4 2.8259 2_565 no H1 O5 1.8633 2_565 no H1 C21 2.6567 2_565 no H1 H2B 2.2849 . no H2A O4 2.1266 1_564 no H2B H1 2.2849 . no H2B O4 1.9420 2_565 no H2B C21 2.8084 2_565 no H4A H15B 2.5098 2_676 no H4A C15 2.9911 2_676 no H4A O6 2.2081 1_564 no H4B C7 2.6171 . no H4B C8 2.8094 . no H4B H7B 2.3848 . no H4B O2 2.3962 2_676 no H4B C15 2.9418 2_676 no H6 H7A 2.3077 . no H6 O7 2.8803 2_566 no H6 O7 2.5931 1_554 no H6 H19A 2.5579 2_566 no H7 C21 2.9517 1_556 no H7 O5 1.8175 1_556 no H7A H19A 2.4814 2_566 no H7A H6 2.3077 . no H7B N2 2.8652 2_575 no H7B N4 2.8347 . no H7B H4B 2.3848 . no H7B H9 2.3111 . no H9 H14A 2.2045 . no H9 C14 2.4773 . no H9 H7B 2.3111 . no H9 H14C 2.3126 . no H13 C5 2.7743 . no H13 C16 2.5322 . no H13 H16A 2.3006 . no H13 H16C 2.3403 . no H14A C9 2.6555 . no H14A H9 2.2045 . no H14A O3 2.7620 2_676 no H14A C12 2.9430 2_676 no H14B H16C 2.5298 1_556 no H14B H14B 2.4419 2_677 no H14C C2 2.9734 1_556 no H14C C9 2.7383 . no H14C H9 2.3126 . no H15A C10 3.0577 . no H15B O6 2.7757 2_667 no H15B N4 2.8911 2_676 no H15B C21 2.9706 2_666 no H15B H4A 2.5098 2_676 no H15C O3 2.7056 . no H15C C12 2.9323 . no H15C H15C 2.3012 2_666 no H16A O6 2.6883 1_554 no H16A C13 2.7377 . no H16A C17 3.0116 1_554 no H16A H13 2.3006 . no H16B O6 2.4007 2_666 no H16C C13 2.7578 . no H16C C14 3.0914 1_554 no H16C H13 2.3403 . no H16C H14B 2.5298 1_554 no H18A H20A 2.4250 . no H18B C10 3.0182 . no H19A O4 2.5879 . no H19A H6 2.5579 2_566 no H19A H7A 2.4814 2_566 no H19B O4 2.7421 . no H19B O6 2.8673 . no H20A H18A 2.4250 . 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 N1 H1 O5 2_565 .8600 1.8633 2.720(3) 174.16 yes N2 H2A O4 1_564 .8599 2.1266 2.890(3) 147.64 yes N2 H2B O4 2_565 .8601 1.9420 2.798(3) 173.23 yes N4 H4A O6 1_564 .8599 2.2081 3.037(3) 161.81 yes N4 H4B O2 2_676 .8603 2.3962 3.053(3) 133.56 yes O7 H7 O5 1_556 .8203 1.8175 2.616(3) 164.12 yes C6 H6 O7 1_554 .9301 2.5931 3.109(3) 115.46 yes C16 H16B O6 2_666 .9600 2.4007 3.355(4) 172.79 yes 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 C14 O1 C10 C9 -.8(3) no C14 O1 C10 C11 -179.96(18) no C15 O2 C11 C10 96.3(2) no C15 O2 C11 C12 -85.6(2) no C16 O3 C12 C11 -178.61(19) no C16 O3 C12 C13 1.5(3) no C6 N1 C2 N2 -179.43(19) no C6 N1 C2 N3 1.0(3) no C2 N1 C6 C5 -1.8(3) no C4 N3 C2 N1 1.3(3) no C2 N3 C4 C5 -2.9(3) no C4 N3 C2 N2 -178.3(2) no C2 N3 C4 N4 178.8(2) no N3 C4 C5 C7 -172.1(2) no N4 C4 C5 C6 -179.6(2) no N4 C4 C5 C7 6.1(3) no N3 C4 C5 C6 2.2(3) no C7 C5 C6 N1 174.68(19) no C4 C5 C7 C8 -72.8(3) no C6 C5 C7 C8 113.2(2) no C4 C5 C6 N1 .2(3) no C5 C7 C8 C13 -36.7(3) no C5 C7 C8 C9 148.4(2) no C7 C8 C13 C12 -174.13(19) no C7 C8 C9 C10 173.84(19) no C9 C8 C13 C12 .6(3) no C13 C8 C9 C10 -1.1(3) no C8 C9 C10 C11 .9(3) no C8 C9 C10 O1 -178.28(17) no C9 C10 C11 O2 178.08(16) no O1 C10 C11 C12 179.14(16) no O1 C10 C11 O2 -2.7(2) no C9 C10 C11 C12 -.1(3) no O2 C11 C12 O3 1.5(3) no C10 C11 C12 C13 -.5(3) no O2 C11 C12 C13 -178.61(17) no C10 C11 C12 O3 179.63(16) no O3 C12 C13 C8 -179.88(18) no C11 C12 C13 C8 .2(3) no O7 C17 C18 C19 -113.2(2) no O6 C17 C18 C19 65.4(3) no C17 C18 C19 C20 172.29(19) no C18 C19 C20 C21 -172.7(2) no C19 C20 C21 O5 175.3(2) no C19 C20 C21 O4 -2.1(3) no