# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Ong, Winston' 'Cheung, Eugene' 'Schultz, Karen' 'Smith, Cartney' 'Bourassa, James' 'Hickey, Magali' _publ_contact_author_name 'Ong, Winston' _publ_contact_author_email winston_ong@hotmail.com _publ_section_title ; Sodium and Potassium Salts of Bumetanide Trihydrate: Impact of Counterion on Structure, Aqueous Solubility and Dehydration Kinetics ; # Attachment '- Publish.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 857276' #TrackingRef '- Publish.cif' _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; # End of 'script/refcif.dat' #end of refcif _cell_length_a 45.797(2) _cell_length_b 5.4342(3) _cell_length_c 17.5936(9) _cell_angle_alpha 90 _cell_angle_beta 102.160(3) _cell_angle_gamma 90 _cell_volume 4280.3(4) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z -x+1/2,-y+1/2,-z -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' K 0.2009 0.2494 8.2186 12.7949 7.4398 0.7748 1.0519 213.1870 0.8659 41.6841 1.4228 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C17 H25 K1 N2 O8 S1 # Dc = 1.42 Fooo = 1920.00 Mu = 3.91 M = 456.56 # Found Formula = C17 H25 K1 N2 O8 S1 # Dc = 1.42 FOOO = 1920.00 Mu = 3.91 M = 456.56 _chemical_formula_sum 'C17 H25 K1 N2 O8 S1' _chemical_formula_moiety 'C17 H25 K1 N2 O8 S1' _chemical_compound_source ? _chemical_formula_weight 456.56 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 100 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_min 0.049 _exptl_crystal_size_mid 0.077 _exptl_crystal_size_max 0.573 _exptl_crystal_density_diffrn 1.417 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 0.391 # Sheldrick geometric approximatio 0.97 0.98 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_process_details 'Apex2 (Bruker AXS, 2006)' _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 92568 _reflns_number_total 9128 _diffrn_reflns_av_R_equivalents 0.039 # Number of reflections with Friedels Law is 9128 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 9154 _diffrn_reflns_theta_min 1.819 _diffrn_reflns_theta_max 34.615 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 34.615 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -72 _diffrn_reflns_limit_h_max 72 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min -72 _reflns_limit_h_max 70 _reflns_limit_k_min 0 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 1.08 _oxford_diffrn_Wilson_scale 23.63 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.82 _refine_diff_density_max 1.06 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 9113 _refine_ls_number_restraints 0 _refine_ls_number_parameters 262 _oxford_refine_ls_R_factor_ref 0.0477 _refine_ls_wR_factor_ref 0.0788 _refine_ls_goodness_of_fit_ref 1.0355 _refine_ls_shift/su_max 0.0010833 _refine_ls_shift/su_mean 0.0006254 # The values computed from all data _oxford_reflns_number_all 9113 _refine_ls_R_factor_all 0.0477 _refine_ls_wR_factor_all 0.0788 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7515 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_gt 0.0697 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 9.67 12.5 3.74 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens K1 K 0.717754(6) 1.51957(5) 0.653401(14) 0.0179 1.0000 Uani . . . . . . . S2 S 0.643962(6) 1.07299(5) 0.573529(14) 0.0118 1.0000 Uani . . . . . . . O3 O 0.66394(2) 1.26826(17) 0.60703(5) 0.0172 1.0000 Uani . . . . . . . O4 O 0.612903(19) 1.10168(18) 0.57524(5) 0.0174 1.0000 Uani . . . . . . . N5 N 0.65817(2) 0.82051(19) 0.61363(5) 0.0153 1.0000 Uani . . . . . . . C6 C 0.64679(2) 1.0291(2) 0.47601(6) 0.0120 1.0000 Uani . . . . . . . C7 C 0.66532(2) 1.1809(2) 0.44310(6) 0.0131 1.0000 Uani . . . . . . . C8 C 0.66740(2) 1.1366(2) 0.36619(6) 0.0119 1.0000 Uani . . . . . . . C9 C 0.68791(2) 1.2939(2) 0.32969(6) 0.0129 1.0000 Uani . . . . . . . O10 O 0.70061(2) 1.47432(18) 0.36816(5) 0.0172 1.0000 Uani . . . . . . . O11 O 0.691768(19) 1.23471(17) 0.26298(5) 0.0155 1.0000 Uani . . . . . . . C12 C 0.65148(2) 0.9443(2) 0.32404(6) 0.0129 1.0000 Uani . . . . . . . C13 C 0.63257(2) 0.7919(2) 0.35647(6) 0.0123 1.0000 Uani . . . . . . . C14 C 0.63048(2) 0.8395(2) 0.43388(6) 0.0120 1.0000 Uani . . . . . . . O15 O 0.613636(18) 0.68373(16) 0.46993(5) 0.0132 1.0000 Uani . . . . . . . C16 C 0.58251(2) 0.7073(2) 0.44911(6) 0.0142 1.0000 Uani . . . . . . . C17 C 0.56845(3) 0.8996(3) 0.40415(8) 0.0211 1.0000 Uani . . . . . . . C18 C 0.53731(3) 0.9064(3) 0.38579(9) 0.0278 1.0000 Uani . . . . . . . C19 C 0.52075(3) 0.7248(3) 0.41237(10) 0.0299 1.0000 Uani . . . . . . . C20 C 0.53530(3) 0.5338(3) 0.45761(10) 0.0289 1.0000 Uani . . . . . . . C21 C 0.56639(3) 0.5231(3) 0.47638(8) 0.0209 1.0000 Uani . . . . . . . N22 N 0.61598(2) 0.6050(2) 0.31717(5) 0.0158 1.0000 Uani . . . . . . . C23 C 0.61567(3) 0.5454(2) 0.23650(6) 0.0165 1.0000 Uani . . . . . . . C24 C 0.59268(3) 0.3456(2) 0.20796(7) 0.0195 1.0000 Uani . . . . . . . C25 C 0.56058(3) 0.4245(3) 0.20487(10) 0.0301 1.0000 Uani . . . . . . . C26 C 0.53827(4) 0.2208(4) 0.17478(12) 0.0440 1.0000 Uani . . . . . . . O27 O 0.72676(2) 0.79787(18) 0.28023(5) 0.0196 1.0000 Uani . . . . . . . O28 O 0.75993(3) 1.3210(3) 0.43178(8) 0.0367 1.0000 Uani . . . . . . . O29 O 0.71933(3) 0.7249(2) 0.50909(6) 0.0310 1.0000 Uani . . . . . . . H203 H 0.6537 0.9062 0.2741 0.0283 1.0000 Uiso . . . . . . . H33 H 0.6766 1.3064 0.4712 0.0177 1.0000 Uiso . . . . . . . H171 H 0.5786 1.0142 0.3893 0.0296 1.0000 Uiso . . . . . . . H181 H 0.5272 1.0410 0.3507 0.0410 1.0000 Uiso . . . . . . . H191 H 0.5003 0.7164 0.3983 0.0390 1.0000 Uiso . . . . . . . H201 H 0.5235 0.4095 0.4748 0.0356 1.0000 Uiso . . . . . . . H211 H 0.5768 0.3937 0.5103 0.0388 1.0000 Uiso . . . . . . . H231 H 0.6352 0.4863 0.2293 0.0237 1.0000 Uiso . . . . . . . H232 H 0.6122 0.6967 0.2076 0.0234 1.0000 Uiso . . . . . . . H241 H 0.5945 0.2893 0.1570 0.0244 1.0000 Uiso . . . . . . . H242 H 0.5974 0.2000 0.2429 0.0263 1.0000 Uiso . . . . . . . H251 H 0.5576 0.5721 0.1691 0.0458 1.0000 Uiso . . . . . . . H252 H 0.5579 0.4908 0.2514 0.0503 1.0000 Uiso . . . . . . . H261 H 0.5179 0.2786 0.1745 0.0795 1.0000 Uiso . . . . . . . H262 H 0.5393 0.1662 0.1231 0.0525 1.0000 Uiso . . . . . . . H263 H 0.5415 0.0638 0.2034 0.0390 1.0000 Uiso . . . . . . . H1 H 0.6476 0.6959 0.6005 0.0336 1.0000 Uiso . . . . . . . H2 H 0.6086 0.5092 0.3418 0.0262 1.0000 Uiso . . . . . . . H3 H 0.7178 0.7038 0.3091 0.0198 1.0000 Uiso . . . . . . . H4 H 0.6664 0.8387 0.6641 0.0408 1.0000 Uiso . . . . . . . H5 H 0.7168 0.9265 0.2716 0.0446 1.0000 Uiso . . . . . . . H14 H 0.7422 1.3892 0.4052 0.0389 1.0000 Uiso . . . . . . . H222 H 0.7660 1.4489 0.4052 0.0500 1.0000 Uiso . . . . . . . H20 H 0.7178 0.8869 0.5159 0.0500 1.0000 Uiso . . . . . . . H23 H 0.7073 0.6835 0.4649 0.0500 1.0000 Uiso . . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 K1 0.01493(10) 0.02461(12) 0.01455(10) -0.00224(9) 0.00365(7) 0.00046(9) S2 0.01425(10) 0.01329(11) 0.00780(9) -0.00010(8) 0.00234(8) 0.00001(8) O3 0.0226(4) 0.0164(4) 0.0122(3) -0.0032(3) 0.0028(3) -0.0045(3) O4 0.0154(3) 0.0235(4) 0.0140(3) -0.0002(3) 0.0049(3) 0.0035(3) N5 0.0199(4) 0.0145(4) 0.0102(4) 0.0011(3) 0.0004(3) 0.0003(3) C6 0.0139(4) 0.0141(4) 0.0079(4) 0.0004(3) 0.0021(3) -0.0002(3) C7 0.0140(4) 0.0156(4) 0.0093(4) -0.0002(3) 0.0018(3) -0.0014(3) C8 0.0116(4) 0.0149(4) 0.0091(4) 0.0009(3) 0.0017(3) -0.0011(3) C9 0.0114(4) 0.0163(4) 0.0106(4) 0.0018(3) 0.0010(3) -0.0010(3) O10 0.0197(4) 0.0188(4) 0.0133(3) -0.0021(3) 0.0040(3) -0.0062(3) O11 0.0171(3) 0.0207(4) 0.0094(3) 0.0001(3) 0.0042(3) -0.0031(3) C12 0.0137(4) 0.0151(4) 0.0098(4) -0.0004(3) 0.0020(3) -0.0019(3) C13 0.0126(4) 0.0144(4) 0.0096(4) -0.0007(3) 0.0017(3) -0.0011(3) C14 0.0123(4) 0.0141(4) 0.0098(4) 0.0007(3) 0.0027(3) -0.0012(3) O15 0.0116(3) 0.0164(3) 0.0115(3) 0.0022(3) 0.0025(2) -0.0015(3) C16 0.0125(4) 0.0167(5) 0.0135(4) -0.0003(4) 0.0026(3) -0.0008(4) C17 0.0165(5) 0.0212(5) 0.0255(6) 0.0067(5) 0.0043(4) 0.0018(4) C18 0.0170(5) 0.0306(7) 0.0344(7) 0.0082(6) 0.0021(5) 0.0054(5) C19 0.0134(5) 0.0343(8) 0.0411(8) 0.0041(6) 0.0037(5) 0.0004(5) C20 0.0162(5) 0.0296(7) 0.0417(8) 0.0059(6) 0.0082(5) -0.0038(5) C21 0.0156(5) 0.0218(6) 0.0257(6) 0.0054(5) 0.0055(4) -0.0017(4) N22 0.0196(4) 0.0180(4) 0.0099(4) -0.0024(3) 0.0036(3) -0.0060(4) C23 0.0167(4) 0.0217(5) 0.0112(4) -0.0038(4) 0.0030(3) -0.0031(4) C24 0.0199(5) 0.0209(5) 0.0160(5) -0.0053(4) 0.0002(4) -0.0029(4) C25 0.0169(5) 0.0303(7) 0.0398(8) -0.0038(6) -0.0016(5) -0.0044(5) C26 0.0293(8) 0.0464(11) 0.0488(10) 0.0023(9) -0.0087(7) -0.0187(8) O27 0.0189(4) 0.0203(4) 0.0205(4) 0.0020(3) 0.0063(3) -0.0021(3) O28 0.0265(5) 0.0405(7) 0.0411(7) -0.0103(6) 0.0026(5) 0.0066(5) O29 0.0376(6) 0.0332(6) 0.0214(5) -0.0060(4) 0.0047(4) 0.0006(5) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.21833(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S2 . O3 . 1.4433(9) yes S2 . O4 . 1.4376(9) yes S2 . N5 . 1.6156(11) yes S2 . C6 . 1.7638(10) yes N5 . H1 . 0.836 no N5 . H4 . 0.895 no C6 . C7 . 1.3941(15) yes C6 . C14 . 1.3911(15) yes C7 . C8 . 1.3972(14) yes C7 . H33 . 0.931 no C8 . C9 . 1.5098(15) yes C8 . C12 . 1.3948(15) yes C9 . O10 . 1.2616(14) yes C9 . O11 . 1.2647(13) yes C12 . C13 . 1.4035(15) yes C12 . H203 . 0.929 no C13 . C14 . 1.4093(14) yes C13 . N22 . 1.3661(15) yes C14 . O15 . 1.3855(13) yes O15 . C16 . 1.4009(13) yes C16 . C17 . 1.3848(17) yes C16 . C21 . 1.3880(17) yes C17 . C18 . 1.3947(18) yes C17 . H171 . 0.851 no C18 . C19 . 1.384(2) yes C18 . H181 . 1.005 no C19 . C20 . 1.390(2) yes C19 . H191 . 0.919 no C20 . C21 . 1.3934(18) yes C20 . H201 . 0.952 no C21 . H211 . 0.978 no N22 . C23 . 1.4527(14) yes N22 . H2 . 0.796 no C23 . C24 . 1.5222(17) yes C23 . H231 . 0.983 no C23 . H232 . 0.963 no C24 . C25 . 1.521(2) yes C24 . H241 . 0.968 no C24 . H242 . 0.997 no C25 . C26 . 1.523(2) yes C25 . H251 . 1.011 no C25 . H252 . 0.927 no C26 . H261 . 0.982 no C26 . H262 . 0.968 no C26 . H263 . 0.986 no O27 . H3 . 0.881 no O27 . H5 . 0.830 no O28 . H14 . 0.924 no O28 . H222 . 0.914 no O29 . H20 . 0.893 no O29 . H23 . 0.883 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 . S2 . O4 . 117.16(6) yes O3 . S2 . N5 . 106.49(5) yes O4 . S2 . N5 . 113.09(6) yes O3 . S2 . C6 . 109.07(5) yes O4 . S2 . C6 . 108.10(5) yes N5 . S2 . C6 . 101.81(5) yes S2 . N5 . H1 . 114.3 no S2 . N5 . H4 . 112.8 no H1 . N5 . H4 . 117.5 no S2 . C6 . C7 . 119.99(8) yes S2 . C6 . C14 . 118.51(8) yes C7 . C6 . C14 . 121.50(9) yes C6 . C7 . C8 . 118.16(10) yes C6 . C7 . H33 . 122.0 no C8 . C7 . H33 . 119.8 no C7 . C8 . C9 . 119.33(10) yes C7 . C8 . C12 . 120.62(10) yes C9 . C8 . C12 . 120.02(9) yes C8 . C9 . O10 . 118.00(9) yes C8 . C9 . O11 . 118.15(10) yes O10 . C9 . O11 . 123.84(10) yes C8 . C12 . C13 . 121.62(10) yes C8 . C12 . H203 . 121.4 no C13 . C12 . H203 . 116.9 no C12 . C13 . C14 . 117.25(10) yes C12 . C13 . N22 . 123.93(10) yes C14 . C13 . N22 . 118.81(10) yes C13 . C14 . C6 . 120.84(10) yes C13 . C14 . O15 . 119.20(10) yes C6 . C14 . O15 . 119.79(9) yes C14 . O15 . C16 . 117.28(9) yes O15 . C16 . C17 . 122.93(10) yes O15 . C16 . C21 . 115.44(10) yes C17 . C16 . C21 . 121.63(11) yes C16 . C17 . C18 . 118.83(12) yes C16 . C17 . H171 . 120.6 no C18 . C17 . H171 . 120.5 no C17 . C18 . C19 . 120.59(13) yes C17 . C18 . H181 . 118.6 no C19 . C18 . H181 . 120.8 no C18 . C19 . C20 . 119.66(12) yes C18 . C19 . H191 . 123.0 no C20 . C19 . H191 . 117.2 no C19 . C20 . C21 . 120.66(13) yes C19 . C20 . H201 . 118.5 no C21 . C20 . H201 . 120.9 no C20 . C21 . C16 . 118.62(12) yes C20 . C21 . H211 . 121.0 no C16 . C21 . H211 . 120.3 no C13 . N22 . C23 . 123.37(10) yes C13 . N22 . H2 . 117.6 no C23 . N22 . H2 . 118.0 no N22 . C23 . C24 . 110.18(10) yes N22 . C23 . H231 . 112.1 no C24 . C23 . H231 . 108.0 no N22 . C23 . H232 . 107.0 no C24 . C23 . H232 . 114.1 no H231 . C23 . H232 . 105.4 no C23 . C24 . C25 . 114.00(11) yes C23 . C24 . H241 . 110.0 no C25 . C24 . H241 . 109.1 no C23 . C24 . H242 . 108.5 no C25 . C24 . H242 . 109.1 no H241 . C24 . H242 . 105.7 no C24 . C25 . C26 . 112.34(15) yes C24 . C25 . H251 . 104.4 no C26 . C25 . H251 . 111.6 no C24 . C25 . H252 . 112.7 no C26 . C25 . H252 . 112.6 no H251 . C25 . H252 . 102.5 no C25 . C26 . H261 . 109.6 no C25 . C26 . H262 . 112.7 no H261 . C26 . H262 . 109.3 no C25 . C26 . H263 . 115.6 no H261 . C26 . H263 . 108.7 no H262 . C26 . H263 . 100.5 no H3 . O27 . H5 . 106.8 no H14 . O28 . H222 . 76.5 no H20 . O29 . H23 . 108.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C21 . H211 . O4 1_545 164 0.98 2.40 3.3534(19) yes C23 . H232 . O4 6_574 144 0.96 2.58 3.4047(19) yes N5 . H1 . O3 1_545 127 0.84 2.44 3.0170(19) yes O27 . H3 . O10 1_545 174 0.88 1.90 2.7749(19) yes N5 . H4 . O11 6_575 158 0.89 1.92 2.7674(19) yes O27 . H5 . O11 . 173 0.83 2.02 2.8445(19) yes