# Electronic Supplementary Material (ESI) for Medicinal Chemistry Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full ChemMedChem _journal_coden_cambridge 0891 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Carmen Navarro Ranniguer' 'Jose Padron' 'del Solar, Virginia' 'Jose Aleman' _publ_contact_author_name 'Jose Aleman' _publ_contact_author_email jose.aleman.lara@gmail.com data_datos_0m _database_code_depnum_ccdc_archive 'CCDC 805611' #TrackingRef 'Compound-7a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H26 Cl2 N2 O3 Pt S2' _chemical_formula_weight 600.48 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9973(4) _cell_length_b 10.8873(6) _cell_length_c 11.5879(6) _cell_angle_alpha 95.196(3) _cell_angle_beta 98.091(3) _cell_angle_gamma 90.511(3) _cell_volume 994.56(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9730 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 33.61 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 2.005 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 7.548 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3136 _exptl_absorpt_correction_T_max 0.7040 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40543 _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_sigmaI/netI 0.0176 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4005 _reflns_number_gt 3849 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0103P)^2^+0.8587P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4005 _refine_ls_number_parameters 242 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0138 _refine_ls_R_factor_gt 0.0126 _refine_ls_wR_factor_ref 0.0311 _refine_ls_wR_factor_gt 0.0307 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pt1 Pt 0.288387(10) 0.365210(7) 1.187613(7) 0.01041(3) Uani 1 1 d . . . S1 S 0.16221(7) 0.52809(5) 1.26174(5) 0.01178(11) Uani 1 1 d . . . S2 S 0.39099(7) 0.08517(5) 0.77911(5) 0.01116(11) Uani 1 1 d . . . C1 C -0.0586(3) 0.5312(2) 1.2168(2) 0.0187(5) Uani 1 1 d . . . H1A H -0.1057 0.6020 1.2587 0.028 Uiso 1 1 calc R . . H1B H -0.1115 0.4549 1.2345 0.028 Uiso 1 1 calc R . . H1C H -0.0809 0.5385 1.1324 0.028 Uiso 1 1 calc R . . C2 C 0.1701(3) 0.5199(2) 1.4142(2) 0.0186(5) Uani 1 1 d . . . H2A H 0.2878 0.5270 1.4519 0.028 Uiso 1 1 calc R . . H2B H 0.1212 0.4408 1.4284 0.028 Uiso 1 1 calc R . . H2C H 0.1056 0.5875 1.4467 0.028 Uiso 1 1 calc R . . C3 C 0.5807(3) 0.2356(2) 1.08358(19) 0.0154(5) Uani 1 1 d . . . H3A H 0.6166 0.1583 1.0432 0.018 Uiso 1 1 calc R . . H3B H 0.6642 0.2572 1.1543 0.018 Uiso 1 1 calc R . . C4 C 0.5788(3) 0.3376(2) 1.00311(19) 0.0143(4) Uani 1 1 d . . . H4A H 0.6949 0.3511 0.9857 0.017 Uiso 1 1 calc R . . H4B H 0.5442 0.4147 1.0444 0.017 Uiso 1 1 calc R . . C5 C 0.4612(3) 0.31145(19) 0.88832(19) 0.0131(4) Uani 1 1 d . . . H5A H 0.3443 0.2983 0.9043 0.016 Uiso 1 1 calc R . . H5B H 0.4624 0.3831 0.8415 0.016 Uiso 1 1 calc R . . C6 C 0.2400(3) 0.12458(19) 0.66029(19) 0.0116(4) Uani 1 1 d . . . C7 C 0.3022(3) 0.15837(19) 0.55939(19) 0.0135(4) Uani 1 1 d . . . C8 C 0.1874(3) 0.1854(2) 0.4642(2) 0.0149(5) Uani 1 1 d . . . C9 C 0.0146(3) 0.18093(19) 0.4657(2) 0.0149(5) Uani 1 1 d . . . C10 C -0.0426(3) 0.1480(2) 0.5659(2) 0.0148(5) Uani 1 1 d . . . C11 C 0.0645(3) 0.11881(19) 0.6650(2) 0.0130(4) Uani 1 1 d . . . C12 C 0.4871(3) 0.1696(2) 0.5474(2) 0.0174(5) Uani 1 1 d . . . H12A H 0.4993 0.1723 0.4647 0.026 Uiso 1 1 calc R . . H12B H 0.5467 0.0983 0.5775 0.026 Uiso 1 1 calc R . . H12C H 0.5355 0.2454 0.5921 0.026 Uiso 1 1 calc R . . C13 C -0.1076(3) 0.2104(2) 0.3609(2) 0.0194(5) Uani 1 1 d . . . H13A H -0.1929 0.1439 0.3407 0.029 Uiso 1 1 calc R . . H13B H -0.0461 0.2183 0.2944 0.029 Uiso 1 1 calc R . . H13C H -0.1631 0.2881 0.3795 0.029 Uiso 1 1 calc R . . C14 C -0.0189(3) 0.0831(2) 0.7667(2) 0.0184(5) Uani 1 1 d . . . H14A H -0.1418 0.0789 0.7441 0.028 Uiso 1 1 calc R . . H14B H 0.0099 0.1449 0.8337 0.028 Uiso 1 1 calc R . . H14C H 0.0210 0.0024 0.7884 0.028 Uiso 1 1 calc R . . Cl1 Cl 0.05785(7) 0.29982(5) 1.05569(5) 0.02136(12) Uani 1 1 d . . . Cl2 Cl 0.52755(7) 0.42265(5) 1.31789(5) 0.01847(11) Uani 1 1 d . . . N1 N 0.4111(3) 0.21469(17) 1.11963(18) 0.0139(4) Uani 1 1 d . . . N2 N 0.5158(2) 0.20112(17) 0.82218(17) 0.0125(4) Uani 1 1 d . . . O1 O 0.2311(2) 0.64905(14) 1.24379(14) 0.0172(3) Uani 1 1 d . . . O2 O 0.4928(2) -0.01088(14) 0.73372(13) 0.0151(3) Uani 1 1 d . . . O3 O 0.3050(2) 0.06212(14) 0.87554(14) 0.0161(3) Uani 1 1 d . . . H1D H 0.422(3) 0.163(3) 1.172(3) 0.021(7) Uiso 1 1 d . . . H1E H 0.342(3) 0.180(2) 1.061(2) 0.011(6) Uiso 1 1 d . . . H2D H 0.593(4) 0.212(2) 0.785(2) 0.017(7) Uiso 1 1 d . . . H8 H 0.227(3) 0.204(2) 0.398(2) 0.020(7) Uiso 1 1 d . . . H10 H -0.156(4) 0.149(2) 0.566(2) 0.017(7) Uiso 1 1 d . . . 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 Pt1 0.01135(5) 0.01087(5) 0.00903(5) 0.00133(3) 0.00118(3) 0.00142(3) S1 0.0115(3) 0.0116(2) 0.0127(3) 0.0012(2) 0.0032(2) 0.0003(2) S2 0.0119(3) 0.0107(2) 0.0106(2) 0.00221(19) -0.0002(2) 0.0002(2) C1 0.0131(12) 0.0192(11) 0.0238(13) 0.0014(10) 0.0030(10) 0.0027(9) C2 0.0245(13) 0.0195(11) 0.0123(11) 0.0001(9) 0.0051(10) 0.0012(10) C3 0.0162(12) 0.0184(11) 0.0113(11) 0.0017(9) 0.0007(9) 0.0065(9) C4 0.0153(11) 0.0136(10) 0.0143(11) 0.0009(8) 0.0032(9) 0.0009(9) C5 0.0148(11) 0.0111(10) 0.0136(11) 0.0017(8) 0.0026(9) 0.0029(8) C6 0.0121(11) 0.0088(10) 0.0126(10) 0.0007(8) -0.0020(9) 0.0004(8) C7 0.0142(11) 0.0114(10) 0.0143(11) 0.0003(8) 0.0005(9) -0.0006(8) C8 0.0183(12) 0.0125(10) 0.0129(11) 0.0010(8) -0.0006(9) -0.0012(9) C9 0.0176(12) 0.0080(10) 0.0167(11) -0.0021(8) -0.0036(9) 0.0011(8) C10 0.0085(11) 0.0130(10) 0.0214(12) -0.0025(9) -0.0002(9) 0.0023(8) C11 0.0138(11) 0.0090(10) 0.0162(11) -0.0003(8) 0.0031(9) 0.0015(8) C12 0.0161(12) 0.0216(12) 0.0150(11) 0.0043(9) 0.0030(9) -0.0029(9) C13 0.0196(13) 0.0166(11) 0.0197(12) 0.0012(9) -0.0052(10) 0.0018(9) C14 0.0142(12) 0.0214(12) 0.0205(12) 0.0011(9) 0.0063(10) 0.0008(9) Cl1 0.0155(3) 0.0251(3) 0.0204(3) -0.0069(2) -0.0026(2) 0.0011(2) Cl2 0.0153(3) 0.0231(3) 0.0150(3) -0.0021(2) -0.0025(2) 0.0036(2) N1 0.0175(10) 0.0125(9) 0.0116(10) 0.0017(8) 0.0012(8) 0.0021(8) N2 0.0116(10) 0.0129(9) 0.0130(9) -0.0003(7) 0.0033(8) -0.0020(7) O1 0.0184(9) 0.0114(7) 0.0236(9) 0.0028(6) 0.0081(7) -0.0016(6) O2 0.0165(8) 0.0136(7) 0.0140(8) 0.0021(6) -0.0022(7) 0.0038(6) O3 0.0181(9) 0.0168(8) 0.0138(8) 0.0045(6) 0.0020(7) -0.0020(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pt1 N1 2.0692(19) . ? Pt1 S1 2.2138(5) . ? Pt1 Cl1 2.2867(6) . ? Pt1 Cl2 2.3072(6) . ? S1 O1 1.4663(16) . ? S1 C2 1.769(2) . ? S1 C1 1.771(2) . ? S2 O3 1.4315(16) . ? S2 O2 1.4383(16) . ? S2 N2 1.6006(19) . ? S2 C6 1.785(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 N1 1.496(3) . ? C3 C4 1.512(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.520(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.469(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.410(3) . ? C6 C11 1.413(3) . ? C7 C8 1.388(3) . ? C7 C12 1.510(3) . ? C8 C9 1.385(3) . ? C8 H8 0.91(3) . ? C9 C10 1.380(3) . ? C9 C13 1.508(3) . ? C10 C11 1.395(3) . ? C10 H10 0.90(3) . ? C11 C14 1.513(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N1 H1D 0.86(3) . ? N1 H1E 0.87(3) . ? N2 H2D 0.81(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Pt1 S1 178.82(6) . . ? N1 Pt1 Cl1 86.73(6) . . ? S1 Pt1 Cl1 94.37(2) . . ? N1 Pt1 Cl2 90.51(6) . . ? S1 Pt1 Cl2 88.39(2) . . ? Cl1 Pt1 Cl2 177.22(2) . . ? O1 S1 C2 107.91(11) . . ? O1 S1 C1 106.72(10) . . ? C2 S1 C1 101.06(12) . . ? O1 S1 Pt1 116.31(7) . . ? C2 S1 Pt1 108.78(8) . . ? C1 S1 Pt1 114.80(8) . . ? O3 S2 O2 118.26(9) . . ? O3 S2 N2 106.77(10) . . ? O2 S2 N2 106.29(10) . . ? O3 S2 C6 109.04(10) . . ? O2 S2 C6 107.30(10) . . ? N2 S2 C6 108.89(10) . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 C2 H2A 109.5 . . ? S1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? S1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N1 C3 C4 111.97(18) . . ? N1 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? N1 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 113.93(19) . . ? C3 C4 H4A 108.8 . . ? C5 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C5 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? N2 C5 C4 109.83(17) . . ? N2 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? N2 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C7 C6 C11 120.9(2) . . ? C7 C6 S2 117.38(16) . . ? C11 C6 S2 121.70(16) . . ? C8 C7 C6 118.6(2) . . ? C8 C7 C12 116.8(2) . . ? C6 C7 C12 124.6(2) . . ? C9 C8 C7 122.1(2) . . ? C9 C8 H8 119.4(17) . . ? C7 C8 H8 118.5(17) . . ? C10 C9 C8 118.0(2) . . ? C10 C9 C13 121.0(2) . . ? C8 C9 C13 121.0(2) . . ? C9 C10 C11 123.4(2) . . ? C9 C10 H10 116.4(16) . . ? C11 C10 H10 120.2(17) . . ? C10 C11 C6 117.0(2) . . ? C10 C11 C14 116.7(2) . . ? C6 C11 C14 126.3(2) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 N1 Pt1 118.31(14) . . ? C3 N1 H1D 108.1(18) . . ? Pt1 N1 H1D 106.8(18) . . ? C3 N1 H1E 110.0(16) . . ? Pt1 N1 H1E 106.5(16) . . ? H1D N1 H1E 107(2) . . ? C5 N2 S2 121.78(16) . . ? C5 N2 H2D 115.5(19) . . ? S2 N2 H2D 117.6(19) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Pt1 S1 O1 44(3) . . . . ? Cl1 Pt1 S1 O1 -114.93(8) . . . . ? Cl2 Pt1 S1 O1 65.32(8) . . . . ? N1 Pt1 S1 C2 -78(3) . . . . ? Cl1 Pt1 S1 C2 123.03(9) . . . . ? Cl2 Pt1 S1 C2 -56.73(9) . . . . ? N1 Pt1 S1 C1 170(3) . . . . ? Cl1 Pt1 S1 C1 10.68(9) . . . . ? Cl2 Pt1 S1 C1 -169.08(9) . . . . ? N1 C3 C4 C5 -61.9(2) . . . . ? C3 C4 C5 N2 -61.7(2) . . . . ? O3 S2 C6 C7 176.04(16) . . . . ? O2 S2 C6 C7 -54.76(19) . . . . ? N2 S2 C6 C7 59.90(19) . . . . ? O3 S2 C6 C11 -5.8(2) . . . . ? O2 S2 C6 C11 123.37(18) . . . . ? N2 S2 C6 C11 -121.98(18) . . . . ? C11 C6 C7 C8 -0.3(3) . . . . ? S2 C6 C7 C8 177.85(16) . . . . ? C11 C6 C7 C12 178.7(2) . . . . ? S2 C6 C7 C12 -3.2(3) . . . . ? C6 C7 C8 C9 0.4(3) . . . . ? C12 C7 C8 C9 -178.6(2) . . . . ? C7 C8 C9 C10 -0.2(3) . . . . ? C7 C8 C9 C13 -179.8(2) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C13 C9 C10 C11 179.4(2) . . . . ? C9 C10 C11 C6 0.3(3) . . . . ? C9 C10 C11 C14 -179.3(2) . . . . ? C7 C6 C11 C10 -0.1(3) . . . . ? S2 C6 C11 C10 -178.12(16) . . . . ? C7 C6 C11 C14 179.5(2) . . . . ? S2 C6 C11 C14 1.4(3) . . . . ? C4 C3 N1 Pt1 -51.3(2) . . . . ? S1 Pt1 N1 C3 -29(3) . . . . ? Cl1 Pt1 N1 C3 129.60(16) . . . . ? Cl2 Pt1 N1 C3 -50.66(16) . . . . ? C4 C5 N2 S2 124.29(18) . . . . ? O3 S2 N2 C5 -44.54(19) . . . . ? O2 S2 N2 C5 -171.64(16) . . . . ? C6 S2 N2 C5 73.05(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2D O1 0.81(3) 2.14(3) 2.819(2) 141(2) 2_667 N1 H1E O3 0.87(3) 2.38(3) 3.151(3) 148(2) . N1 H1D O2 0.86(3) 2.13(3) 2.958(2) 161(2) 2_657 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.919 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.076