# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Xingang Zhang' _publ_contact_author_email xgzhang@mail.sioc.ac.cn loop_ _publ_author_name 'Xingang Zhang' 'Gaochao Huang' 'Jie Yang' data_cd21196 _database_code_depnum_ccdc_archive 'CCDC 816912' #TrackingRef 'cd21196.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 F3 N2 O3 S' _chemical_formula_weight 420.40 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.8900(12) _cell_length_b 12.890(3) _cell_length_c 26.170(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1986.9(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4571 _cell_measurement_theta_min 4.434 _cell_measurement_theta_max 48.347 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.378 _exptl_crystal_size_mid 0.311 _exptl_crystal_size_min 0.256 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.78779 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10836 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3900 _reflns_number_gt 3509 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0640P)^2^+0.2691P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.01(9) _chemical_absolute_configuration ad _refine_ls_number_reflns 3900 _refine_ls_number_parameters 268 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.091 _refine_ls_shift/su_max 0.000 _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 S1 S 0.52788(12) -0.14299(5) 0.12631(3) 0.0674(2) Uani 1 1 d . . . F1 F 0.0987(3) 0.34258(19) 0.14340(10) 0.1191(8) Uani 1 1 d . . . F2 F 0.0884(3) 0.1903(2) 0.17653(10) 0.1185(7) Uani 1 1 d . . . F3 F 0.0826(4) 0.2082(3) 0.09634(10) 0.1408(10) Uani 1 1 d . . . N1 N 0.8477(4) -0.06290(15) 0.07149(7) 0.0582(5) Uani 1 1 d . . . N2 N 0.5125(4) 0.27785(16) 0.18674(7) 0.0589(5) Uani 1 1 d . . . O1 O 0.6090(5) 0.40536(16) 0.11187(7) 0.0854(6) Uani 1 1 d . . . O2 O 0.4479(7) 0.30603(17) 0.05314(7) 0.1118(10) Uani 1 1 d . . . O3 O 0.8114(3) 0.34756(14) 0.24964(6) 0.0669(5) Uani 1 1 d . . . C1 C 0.4341(4) 0.24550(18) 0.13735(8) 0.0546(5) Uani 1 1 d . . . C2 C 0.5170(4) 0.14354(18) 0.12073(9) 0.0559(5) Uani 1 1 d . . . C3 C 0.5935(5) 0.06207(19) 0.10896(8) 0.0564(6) Uani 1 1 d . . . C4 C 0.6742(4) -0.03992(17) 0.09881(8) 0.0524(5) Uani 1 1 d . . . C5 C 0.7188(4) -0.22619(18) 0.09810(9) 0.0560(5) Uani 1 1 d . . . C6 C 0.8770(4) -0.16943(18) 0.07059(8) 0.0524(5) Uani 1 1 d . . . C7 C 1.0494(5) -0.2217(2) 0.04517(9) 0.0677(7) Uani 1 1 d . . . H7 H 1.1573 -0.1850 0.0265 0.081 Uiso 1 1 calc R . . C8 C 1.0593(5) -0.3269(2) 0.04773(10) 0.0722(7) Uani 1 1 d . . . H8 H 1.1748 -0.3621 0.0308 0.087 Uiso 1 1 calc R . . C9 C 0.9003(6) -0.3821(2) 0.07514(11) 0.0757(8) Uani 1 1 d . . . H9 H 0.9109 -0.4540 0.0766 0.091 Uiso 1 1 calc R . . C10 C 0.7294(6) -0.3339(2) 0.09995(11) 0.0724(7) Uani 1 1 d . . . H10 H 0.6213 -0.3719 0.1179 0.087 Uiso 1 1 calc R . . C11 C 0.1697(5) 0.2450(3) 0.13856(12) 0.0828(9) Uani 1 1 d . . . C12 C 0.5106(6) 0.32941(19) 0.09938(9) 0.0645(6) Uani 1 1 d . . . C13 C 0.4940(14) 0.3847(3) 0.01462(13) 0.150(2) Uani 1 1 d U . . H13A H 0.4391 0.4507 0.0263 0.225 Uiso 1 1 calc R . . H13B H 0.4187 0.3665 -0.0166 0.225 Uiso 1 1 calc R . . H13C H 0.6547 0.3889 0.0088 0.225 Uiso 1 1 calc R . . C14 C 0.5778(4) 0.21195(17) 0.22652(8) 0.0533(5) Uani 1 1 d . . . C15 C 0.4909(6) 0.1141(2) 0.23557(10) 0.0734(8) Uani 1 1 d . . . H15 H 0.3804 0.0872 0.2139 0.088 Uiso 1 1 calc R . . C16 C 0.5668(8) 0.0559(2) 0.27649(12) 0.0901(11) Uani 1 1 d . . . H16 H 0.5058 -0.0095 0.2824 0.108 Uiso 1 1 calc R . . C17 C 0.7286(8) 0.0933(2) 0.30797(11) 0.0903(11) Uani 1 1 d . . . H17 H 0.7807 0.0528 0.3349 0.108 Uiso 1 1 calc R . . C18 C 0.8165(6) 0.1902(2) 0.30054(10) 0.0730(7) Uani 1 1 d . . . H18 H 0.9267 0.2160 0.3226 0.088 Uiso 1 1 calc R . . C19 C 0.7405(4) 0.24965(18) 0.26005(8) 0.0554(6) Uani 1 1 d . . . C20 C 0.9972(6) 0.3881(3) 0.27795(12) 0.0869(9) Uani 1 1 d . . . H20A H 0.9548 0.3947 0.3132 0.130 Uiso 1 1 calc R . . H20B H 1.0377 0.4550 0.2647 0.130 Uiso 1 1 calc R . . H20C H 1.1246 0.3420 0.2751 0.130 Uiso 1 1 calc R . . H2 H 0.597(5) 0.329(2) 0.1877(10) 0.058(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 S1 0.0656(4) 0.0571(3) 0.0794(4) 0.0026(3) 0.0187(3) -0.0060(3) F1 0.0762(11) 0.1283(17) 0.1528(19) -0.0282(15) -0.0070(13) 0.0415(12) F2 0.0703(11) 0.1474(19) 0.1377(17) -0.0060(15) 0.0327(13) -0.0168(12) F3 0.0764(12) 0.211(3) 0.1355(18) -0.0652(18) -0.0336(13) -0.0083(15) N1 0.0732(13) 0.0506(10) 0.0508(10) -0.0008(8) 0.0096(10) -0.0035(10) N2 0.0742(13) 0.0488(10) 0.0536(10) -0.0057(8) -0.0055(10) -0.0072(11) O1 0.1197(18) 0.0693(12) 0.0673(11) 0.0082(9) -0.0051(11) -0.0136(12) O2 0.208(3) 0.0756(12) 0.0523(10) -0.0011(9) -0.0206(15) -0.0039(18) O3 0.0770(11) 0.0599(10) 0.0636(9) 0.0017(8) -0.0117(9) -0.0117(9) C1 0.0557(12) 0.0557(12) 0.0524(11) -0.0116(10) -0.0023(10) 0.0009(10) C2 0.0586(13) 0.0554(12) 0.0537(11) -0.0078(10) 0.0052(10) -0.0071(11) C3 0.0647(14) 0.0534(13) 0.0510(12) -0.0047(9) 0.0032(10) -0.0054(11) C4 0.0620(14) 0.0493(12) 0.0459(11) -0.0027(9) 0.0002(11) -0.0057(10) C5 0.0632(14) 0.0516(12) 0.0533(12) 0.0004(10) -0.0011(11) -0.0040(11) C6 0.0620(13) 0.0515(12) 0.0438(10) -0.0013(9) -0.0008(10) -0.0024(10) C7 0.0766(17) 0.0677(15) 0.0588(13) -0.0010(11) 0.0131(12) -0.0006(14) C8 0.0820(18) 0.0668(16) 0.0677(15) -0.0078(12) 0.0046(14) 0.0162(14) C9 0.098(2) 0.0514(14) 0.0777(17) -0.0038(12) -0.0050(16) 0.0072(14) C10 0.0847(19) 0.0536(14) 0.0790(16) 0.0046(12) 0.0031(15) -0.0093(13) C11 0.0668(17) 0.099(2) 0.0826(19) -0.0283(18) -0.0030(16) 0.0079(17) C12 0.0873(18) 0.0522(12) 0.0540(12) -0.0078(10) -0.0060(13) 0.0139(13) C13 0.292(7) 0.098(2) 0.0602(17) 0.0186(17) -0.009(3) -0.002(4) C14 0.0662(14) 0.0492(12) 0.0445(10) -0.0035(9) 0.0098(10) 0.0007(10) C15 0.099(2) 0.0610(14) 0.0605(13) -0.0061(11) 0.0171(16) -0.0196(15) C16 0.143(3) 0.0570(15) 0.0699(17) 0.0097(13) 0.026(2) -0.0138(18) C17 0.147(3) 0.0659(17) 0.0578(15) 0.0114(13) 0.0065(19) 0.012(2) C18 0.0904(19) 0.0735(17) 0.0552(13) 0.0005(12) -0.0036(14) 0.0121(15) C19 0.0663(14) 0.0508(13) 0.0490(11) -0.0022(9) 0.0066(10) 0.0038(11) C20 0.080(2) 0.103(2) 0.0772(17) -0.0011(16) -0.0121(16) -0.0277(19) _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 S1 C5 1.720(3) . ? S1 C4 1.740(2) . ? F1 C11 1.331(4) . ? F2 C11 1.309(4) . ? F3 C11 1.307(4) . ? N1 C4 1.282(3) . ? N1 C6 1.384(3) . ? N2 C14 1.398(3) . ? N2 C1 1.434(3) . ? N2 H2 0.82(3) . ? O1 C12 1.184(3) . ? O2 C12 1.300(3) . ? O2 C13 1.455(4) . ? O3 C19 1.357(3) . ? O3 C20 1.421(3) . ? C1 C2 1.468(3) . ? C1 C12 1.536(4) . ? C1 C11 1.558(4) . ? C2 C3 1.183(3) . ? C3 C4 1.423(3) . ? C5 C6 1.386(3) . ? C5 C10 1.391(4) . ? C6 C7 1.389(4) . ? C7 C8 1.359(4) . ? C7 H7 0.9300 . ? C8 C9 1.378(4) . ? C8 H8 0.9300 . ? C9 C10 1.349(5) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.381(3) . ? C14 C19 1.387(3) . ? C15 C16 1.382(4) . ? C15 H15 0.9300 . ? C16 C17 1.348(6) . ? C16 H16 0.9300 . ? C17 C18 1.366(5) . ? C17 H17 0.9300 . ? C18 C19 1.382(3) . ? C18 H18 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 C5 S1 C4 88.54(11) . . ? C4 N1 C6 109.8(2) . . ? C14 N2 C1 125.67(19) . . ? C14 N2 H2 107.1(18) . . ? C1 N2 H2 117.0(18) . . ? C12 O2 C13 115.5(3) . . ? C19 O3 C20 118.3(2) . . ? N2 C1 C2 114.8(2) . . ? N2 C1 C12 106.49(19) . . ? C2 C1 C12 109.94(19) . . ? N2 C1 C11 107.7(2) . . ? C2 C1 C11 109.6(2) . . ? C12 C1 C11 108.0(2) . . ? C3 C2 C1 176.5(3) . . ? C2 C3 C4 174.6(3) . . ? N1 C4 C3 125.7(2) . . ? N1 C4 S1 116.69(17) . . ? C3 C4 S1 117.57(18) . . ? C6 C5 C10 121.0(3) . . ? C6 C5 S1 109.46(17) . . ? C10 C5 S1 129.5(2) . . ? N1 C6 C5 115.5(2) . . ? N1 C6 C7 125.5(2) . . ? C5 C6 C7 119.0(2) . . ? C8 C7 C6 119.5(3) . . ? C8 C7 H7 120.3 . . ? C6 C7 H7 120.3 . . ? C7 C8 C9 120.8(3) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C10 C9 C8 121.4(2) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C5 118.4(3) . . ? C9 C10 H10 120.8 . . ? C5 C10 H10 120.8 . . ? F3 C11 F2 107.6(3) . . ? F3 C11 F1 107.5(3) . . ? F2 C11 F1 108.8(3) . . ? F3 C11 C1 112.1(3) . . ? F2 C11 C1 112.5(3) . . ? F1 C11 C1 108.2(3) . . ? O1 C12 O2 126.0(3) . . ? O1 C12 C1 123.2(2) . . ? O2 C12 C1 110.8(2) . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 117.9(2) . . ? C15 C14 N2 125.5(2) . . ? C19 C14 N2 116.6(2) . . ? C14 C15 C16 120.6(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C17 C16 C15 120.6(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 120.5(3) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C17 C18 C19 119.6(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? O3 C19 C18 124.7(3) . . ? O3 C19 C14 114.3(2) . . ? C18 C19 C14 121.0(2) . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 C14 N2 C1 C2 -26.5(4) . . . . ? C14 N2 C1 C12 -148.4(2) . . . . ? C14 N2 C1 C11 95.9(3) . . . . ? N2 C1 C2 C3 -26(4) . . . . ? C12 C1 C2 C3 94(4) . . . . ? C11 C1 C2 C3 -147(4) . . . . ? C1 C2 C3 C4 88(5) . . . . ? C6 N1 C4 C3 179.2(2) . . . . ? C6 N1 C4 S1 0.0(3) . . . . ? C2 C3 C4 N1 -161(3) . . . . ? C2 C3 C4 S1 19(3) . . . . ? C5 S1 C4 N1 -0.2(2) . . . . ? C5 S1 C4 C3 -179.5(2) . . . . ? C4 S1 C5 C6 0.25(17) . . . . ? C4 S1 C5 C10 -179.8(3) . . . . ? C4 N1 C6 C5 0.2(3) . . . . ? C4 N1 C6 C7 -179.3(2) . . . . ? C10 C5 C6 N1 179.7(2) . . . . ? S1 C5 C6 N1 -0.3(3) . . . . ? C10 C5 C6 C7 -0.8(4) . . . . ? S1 C5 C6 C7 179.18(19) . . . . ? N1 C6 C7 C8 179.5(3) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 0.4(5) . . . . ? C8 C9 C10 C5 -1.1(5) . . . . ? C6 C5 C10 C9 1.3(4) . . . . ? S1 C5 C10 C9 -178.7(2) . . . . ? N2 C1 C11 F3 -174.7(3) . . . . ? C2 C1 C11 F3 -49.1(4) . . . . ? C12 C1 C11 F3 70.6(3) . . . . ? N2 C1 C11 F2 -53.3(3) . . . . ? C2 C1 C11 F2 72.3(3) . . . . ? C12 C1 C11 F2 -167.9(2) . . . . ? N2 C1 C11 F1 66.9(3) . . . . ? C2 C1 C11 F1 -167.5(2) . . . . ? C12 C1 C11 F1 -47.7(3) . . . . ? C13 O2 C12 O1 -3.7(6) . . . . ? C13 O2 C12 C1 174.8(4) . . . . ? N2 C1 C12 O1 -1.9(4) . . . . ? C2 C1 C12 O1 -126.9(3) . . . . ? C11 C1 C12 O1 113.6(3) . . . . ? N2 C1 C12 O2 179.5(3) . . . . ? C2 C1 C12 O2 54.5(3) . . . . ? C11 C1 C12 O2 -65.0(3) . . . . ? C1 N2 C14 C15 -30.7(4) . . . . ? C1 N2 C14 C19 150.6(2) . . . . ? C19 C14 C15 C16 -0.7(4) . . . . ? N2 C14 C15 C16 -179.4(3) . . . . ? C14 C15 C16 C17 -0.6(5) . . . . ? C15 C16 C17 C18 1.4(5) . . . . ? C16 C17 C18 C19 -0.8(5) . . . . ? C20 O3 C19 C18 8.5(4) . . . . ? C20 O3 C19 C14 -172.4(2) . . . . ? C17 C18 C19 O3 178.4(3) . . . . ? C17 C18 C19 C14 -0.6(4) . . . . ? C15 C14 C19 O3 -177.8(2) . . . . ? N2 C14 C19 O3 1.0(3) . . . . ? C15 C14 C19 C18 1.4(4) . . . . ? N2 C14 C19 C18 -179.9(2) . . . . ? 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 H2 O3 0.82(3) 2.07(3) 2.572(3) 119(2) . N2 H2 O1 0.82(3) 2.22(3) 2.620(3) 110(2) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.238 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.035