data_13158z _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 13158z _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 N2 O5 S' _chemical_formula_sum 'C22 H22 N2 O5 S' _chemical_formula_weight 426.48 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' _symmetry_cell_setting 'Monoclinic' _symmetry_space_group_name_H-M 'P2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6141(10) _cell_length_b 20.396(2) _cell_length_c 12.2349(14) _cell_angle_alpha 90.00 _cell_angle_beta 106.345(2) _cell_angle_gamma 90.00 _cell_volume 2062.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2953 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.53 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'SADABS(Sheldrick, 2008)' _exptl_special_details 'Xiao-Na Wang / Prof. R Hsung' _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21528 _diffrn_reflns_av_R_equivalents 0.0590 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.80 _reflns_number_total 3963 _reflns_number_gt 2866 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0371P)^2^+1.0691P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3963 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1009 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.20503(7) 0.46376(3) 0.33757(4) 0.02386(15) Uani 1 1 d . . . O1 O 0.29600(18) 0.46269(7) 0.45569(12) 0.0281(4) Uani 1 1 d . . . O2 O 0.06557(18) 0.42334(7) 0.29747(12) 0.0297(4) Uani 1 1 d . . . O3 O 0.7760(2) 0.44014(9) 0.07101(14) 0.0407(4) Uani 1 1 d . . . O4 O 0.5688(2) 0.40800(9) -0.06192(13) 0.0423(5) Uani 1 1 d . . . O5 O 0.63222(17) 0.66244(7) 0.42593(13) 0.0289(4) Uani 1 1 d . . . H5A H 0.6539 0.6253 0.4560 0.043 Uiso 1 1 calc R . . N1 N 0.6327(2) 0.42582(9) 0.03538(15) 0.0277(4) Uani 1 1 d . . . N2 N 0.1488(2) 0.53999(8) 0.30645(14) 0.0216(4) Uani 1 1 d . . . C1 C 0.3382(3) 0.44574(10) 0.25451(17) 0.0228(5) Uani 1 1 d . . . C2 C 0.2730(3) 0.42002(10) 0.14579(18) 0.0269(5) Uani 1 1 d . . . H2B H 0.1622 0.4078 0.1210 0.032 Uiso 1 1 calc R . . C3 C 0.3709(3) 0.41240(10) 0.07408(18) 0.0262(5) Uani 1 1 d . . . H3A H 0.3289 0.3950 -0.0004 0.031 Uiso 1 1 calc R . . C4 C 0.5313(3) 0.43087(10) 0.11422(17) 0.0230(5) Uani 1 1 d . . . C5 C 0.5996(3) 0.45442(10) 0.22314(18) 0.0263(5) Uani 1 1 d . . . H5B H 0.7115 0.4649 0.2486 0.032 Uiso 1 1 calc R . . C6 C 0.5016(3) 0.46235(10) 0.29417(18) 0.0254(5) Uani 1 1 d . . . H6A H 0.5449 0.4789 0.3692 0.030 Uiso 1 1 calc R . . C7 C 0.0606(3) 0.55245(10) 0.18458(17) 0.0256(5) Uani 1 1 d . . . H7A H -0.0196 0.5172 0.1565 0.031 Uiso 1 1 calc R . . H7B H 0.1383 0.5517 0.1384 0.031 Uiso 1 1 calc R . . C8 C -0.0245(3) 0.61760(11) 0.17024(17) 0.0251(5) Uani 1 1 d . . . C9 C -0.1284(3) 0.63418(12) 0.23430(19) 0.0315(6) Uani 1 1 d . . . H9A H -0.1447 0.6044 0.2898 0.038 Uiso 1 1 calc R . . C10 C -0.2085(3) 0.69378(13) 0.2180(2) 0.0384(6) Uani 1 1 d . . . H10A H -0.2777 0.7051 0.2633 0.046 Uiso 1 1 calc R . . C11 C -0.1880(3) 0.73686(13) 0.1357(2) 0.0391(6) Uani 1 1 d . . . H11A H -0.2435 0.7777 0.1242 0.047 Uiso 1 1 calc R . . C12 C -0.0872(3) 0.72045(12) 0.0706(2) 0.0340(6) Uani 1 1 d . . . H12A H -0.0749 0.7496 0.0130 0.041 Uiso 1 1 calc R . . C13 C -0.0035(3) 0.66154(11) 0.08867(18) 0.0267(5) Uani 1 1 d . . . H13A H 0.0687 0.6511 0.0451 0.032 Uiso 1 1 calc R . . C14 C 0.2622(2) 0.59016(10) 0.36106(17) 0.0209(5) Uani 1 1 d . . . C15 C 0.2524(3) 0.62191(10) 0.46649(17) 0.0239(5) Uani 1 1 d . . . C16 C 0.1439(3) 0.60911(11) 0.52220(19) 0.0302(5) Uani 1 1 d . . . H16A H 0.0631 0.5768 0.4941 0.036 Uiso 1 1 calc R . . H16B H 0.1471 0.6323 0.5901 0.036 Uiso 1 1 calc R . . C17 C 0.3829(3) 0.67437(11) 0.49431(19) 0.0267(5) Uani 1 1 d . . . H17A H 0.4652 0.6651 0.5685 0.032 Uiso 1 1 calc R . . C18 C 0.4609(3) 0.67222(10) 0.39302(18) 0.0236(5) Uani 1 1 d . . . C19 C 0.3732(2) 0.61746(10) 0.31902(17) 0.0230(5) Uani 1 1 d . . . H19A H 0.3946 0.6039 0.2504 0.028 Uiso 1 1 calc R . . C20 C 0.4244(3) 0.73952(11) 0.3349(2) 0.0313(5) Uani 1 1 d . . . H20A H 0.5161 0.7701 0.3638 0.038 Uiso 1 1 calc R . . H20B H 0.4023 0.7354 0.2512 0.038 Uiso 1 1 calc R . . C21 C 0.2751(3) 0.76307(12) 0.3662(2) 0.0382(6) Uani 1 1 d . . . H21A H 0.1763 0.7406 0.3205 0.046 Uiso 1 1 calc R . . H21B H 0.2607 0.8110 0.3559 0.046 Uiso 1 1 calc R . . C22 C 0.3147(3) 0.74402(11) 0.4921(2) 0.0357(6) Uani 1 1 d . . . H22A H 0.2164 0.7444 0.5187 0.043 Uiso 1 1 calc R . . H22B H 0.3959 0.7741 0.5401 0.043 Uiso 1 1 calc R . . 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 0.0298(3) 0.0214(3) 0.0203(3) 0.0008(2) 0.0069(2) -0.0021(2) O1 0.0380(9) 0.0266(8) 0.0190(8) 0.0025(7) 0.0067(7) 0.0012(7) O2 0.0337(9) 0.0270(9) 0.0291(9) -0.0004(7) 0.0098(7) -0.0090(7) O3 0.0321(10) 0.0541(12) 0.0378(10) -0.0073(8) 0.0128(8) -0.0101(8) O4 0.0429(10) 0.0606(12) 0.0239(9) -0.0103(8) 0.0101(8) -0.0055(9) O5 0.0256(8) 0.0289(9) 0.0306(9) 0.0028(7) 0.0052(7) -0.0025(7) N1 0.0341(12) 0.0236(10) 0.0256(11) 0.0010(8) 0.0088(9) 0.0005(9) N2 0.0244(10) 0.0205(9) 0.0181(9) 0.0006(7) 0.0033(7) -0.0014(8) C1 0.0286(12) 0.0184(11) 0.0204(11) 0.0005(9) 0.0052(9) 0.0006(9) C2 0.0294(13) 0.0242(12) 0.0248(12) -0.0028(9) 0.0040(10) -0.0011(10) C3 0.0307(13) 0.0239(12) 0.0200(11) -0.0031(9) 0.0007(10) 0.0002(10) C4 0.0301(12) 0.0174(11) 0.0218(11) 0.0009(9) 0.0079(9) 0.0029(9) C5 0.0265(12) 0.0243(12) 0.0253(12) 0.0007(10) 0.0028(10) -0.0004(10) C6 0.0321(13) 0.0222(12) 0.0187(11) -0.0012(9) 0.0021(9) -0.0005(10) C7 0.0269(12) 0.0268(12) 0.0202(11) -0.0006(9) 0.0020(9) -0.0029(10) C8 0.0228(12) 0.0293(12) 0.0207(11) 0.0004(9) 0.0017(9) -0.0026(10) C9 0.0295(13) 0.0365(14) 0.0287(13) 0.0089(11) 0.0086(10) 0.0023(11) C10 0.0327(14) 0.0507(16) 0.0341(14) 0.0040(12) 0.0130(11) 0.0122(12) C11 0.0373(15) 0.0366(15) 0.0408(15) 0.0069(12) 0.0067(12) 0.0132(12) C12 0.0360(14) 0.0319(14) 0.0334(13) 0.0096(11) 0.0085(11) 0.0009(11) C13 0.0247(12) 0.0305(13) 0.0244(12) 0.0015(10) 0.0064(10) -0.0027(10) C14 0.0246(11) 0.0185(11) 0.0182(11) -0.0007(9) 0.0038(9) 0.0013(9) C15 0.0279(12) 0.0238(12) 0.0198(11) 0.0011(9) 0.0063(9) 0.0034(9) C16 0.0348(13) 0.0342(14) 0.0235(12) -0.0014(10) 0.0113(10) 0.0011(11) C17 0.0321(13) 0.0258(12) 0.0232(12) -0.0035(9) 0.0092(10) -0.0017(10) C18 0.0244(12) 0.0227(12) 0.0230(11) -0.0008(9) 0.0054(9) -0.0002(9) C19 0.0269(12) 0.0228(11) 0.0198(11) -0.0022(9) 0.0075(9) 0.0015(9) C20 0.0408(14) 0.0238(12) 0.0281(13) 0.0017(10) 0.0076(11) -0.0020(11) C21 0.0398(15) 0.0210(13) 0.0497(16) -0.0033(11) 0.0058(12) 0.0018(11) C22 0.0400(15) 0.0295(13) 0.0403(15) -0.0117(11) 0.0158(12) -0.0025(11) _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 O2 1.4253(15) . ? S1 O1 1.4372(15) . ? S1 N2 1.6412(18) . ? S1 C1 1.772(2) . ? O3 N1 1.223(2) . ? O4 N1 1.218(2) . ? O5 C18 1.430(2) . ? O5 H5A 0.8400 . ? N1 C4 1.476(3) . ? N2 C14 1.442(3) . ? N2 C7 1.492(3) . ? C1 C2 1.393(3) . ? C1 C6 1.395(3) . ? C2 C3 1.386(3) . ? C2 H2B 0.9500 . ? C3 C4 1.383(3) . ? C3 H3A 0.9500 . ? C4 C5 1.382(3) . ? C5 C6 1.381(3) . ? C5 H5B 0.9500 . ? C6 H6A 0.9500 . ? C7 C8 1.504(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.388(3) . ? C8 C13 1.391(3) . ? C9 C10 1.384(3) . ? C9 H9A 0.9500 . ? C10 C11 1.385(3) . ? C10 H10A 0.9500 . ? C11 C12 1.375(3) . ? C11 H11A 0.9500 . ? C12 C13 1.387(3) . ? C12 H12A 0.9500 . ? C13 H13A 0.9500 . ? C14 C19 1.329(3) . ? C14 C15 1.467(3) . ? C15 C16 1.329(3) . ? C15 C17 1.519(3) . ? C16 H16A 0.9500 . ? C16 H16B 0.9500 . ? C17 C22 1.535(3) . ? C17 C18 1.568(3) . ? C17 H17A 1.0000 . ? C18 C19 1.501(3) . ? C18 C20 1.537(3) . ? C19 H19A 0.9500 . ? C20 C21 1.520(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 C22 1.530(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 O2 S1 O1 120.37(9) . . ? O2 S1 N2 107.62(9) . . ? O1 S1 N2 106.83(9) . . ? O2 S1 C1 107.56(10) . . ? O1 S1 C1 108.41(10) . . ? N2 S1 C1 105.06(9) . . ? C18 O5 H5A 109.5 . . ? O4 N1 O3 123.59(19) . . ? O4 N1 C4 118.13(18) . . ? O3 N1 C4 118.28(18) . . ? C14 N2 C7 115.46(16) . . ? C14 N2 S1 116.58(13) . . ? C7 N2 S1 115.29(13) . . ? C2 C1 C6 121.3(2) . . ? C2 C1 S1 118.28(17) . . ? C6 C1 S1 120.18(16) . . ? C3 C2 C1 119.6(2) . . ? C3 C2 H2B 120.2 . . ? C1 C2 H2B 120.2 . . ? C4 C3 C2 118.0(2) . . ? C4 C3 H3A 121.0 . . ? C2 C3 H3A 121.0 . . ? C5 C4 C3 123.3(2) . . ? C5 C4 N1 119.00(19) . . ? C3 C4 N1 117.73(19) . . ? C6 C5 C4 118.5(2) . . ? C6 C5 H5B 120.7 . . ? C4 C5 H5B 120.7 . . ? C5 C6 C1 119.2(2) . . ? C5 C6 H6A 120.4 . . ? C1 C6 H6A 120.4 . . ? N2 C7 C8 111.18(17) . . ? N2 C7 H7A 109.4 . . ? C8 C7 H7A 109.4 . . ? N2 C7 H7B 109.4 . . ? C8 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C13 118.9(2) . . ? C9 C8 C7 121.4(2) . . ? C13 C8 C7 119.7(2) . . ? C10 C9 C8 120.5(2) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C9 C10 C11 120.1(2) . . ? C9 C10 H10A 119.9 . . ? C11 C10 H10A 119.9 . . ? C12 C11 C10 119.8(2) . . ? C12 C11 H11A 120.1 . . ? C10 C11 H11A 120.1 . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12A 119.9 . . ? C13 C12 H12A 119.9 . . ? C12 C13 C8 120.4(2) . . ? C12 C13 H13A 119.8 . . ? C8 C13 H13A 119.8 . . ? C19 C14 N2 125.82(19) . . ? C19 C14 C15 112.39(19) . . ? N2 C14 C15 121.45(18) . . ? C16 C15 C14 126.0(2) . . ? C16 C15 C17 127.3(2) . . ? C14 C15 C17 106.62(18) . . ? C15 C16 H16A 120.0 . . ? C15 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? C15 C17 C22 113.10(19) . . ? C15 C17 C18 104.94(17) . . ? C22 C17 C18 105.00(18) . . ? C15 C17 H17A 111.2 . . ? C22 C17 H17A 111.2 . . ? C18 C17 H17A 111.2 . . ? O5 C18 C19 111.72(17) . . ? O5 C18 C20 108.38(17) . . ? C19 C18 C20 112.49(17) . . ? O5 C18 C17 114.77(17) . . ? C19 C18 C17 104.06(17) . . ? C20 C18 C17 105.29(17) . . ? C14 C19 C18 111.91(18) . . ? C14 C19 H19A 124.0 . . ? C18 C19 H19A 124.0 . . ? C21 C20 C18 104.04(18) . . ? C21 C20 H20A 110.9 . . ? C18 C20 H20A 110.9 . . ? C21 C20 H20B 110.9 . . ? C18 C20 H20B 110.9 . . ? H20A C20 H20B 109.0 . . ? C20 C21 C22 102.05(19) . . ? C20 C21 H21A 111.4 . . ? C22 C21 H21A 111.4 . . ? C20 C21 H21B 111.4 . . ? C22 C21 H21B 111.4 . . ? H21A C21 H21B 109.2 . . ? C21 C22 C17 103.23(18) . . ? C21 C22 H22A 111.1 . . ? C17 C22 H22A 111.1 . . ? C21 C22 H22B 111.1 . . ? C17 C22 H22B 111.1 . . ? H22A C22 H22B 109.1 . . ? 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 O2 S1 N2 C14 166.72(14) . . . . ? O1 S1 N2 C14 36.16(17) . . . . ? C1 S1 N2 C14 -78.86(16) . . . . ? O2 S1 N2 C7 -53.10(17) . . . . ? O1 S1 N2 C7 176.33(14) . . . . ? C1 S1 N2 C7 61.31(16) . . . . ? O2 S1 C1 C2 24.54(19) . . . . ? O1 S1 C1 C2 156.16(16) . . . . ? N2 S1 C1 C2 -89.92(18) . . . . ? O2 S1 C1 C6 -160.82(17) . . . . ? O1 S1 C1 C6 -29.2(2) . . . . ? N2 S1 C1 C6 84.72(18) . . . . ? C6 C1 C2 C3 -1.9(3) . . . . ? S1 C1 C2 C3 172.72(16) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C3 C4 C5 2.2(3) . . . . ? C2 C3 C4 N1 -176.91(18) . . . . ? O4 N1 C4 C5 -176.5(2) . . . . ? O3 N1 C4 C5 3.0(3) . . . . ? O4 N1 C4 C3 2.6(3) . . . . ? O3 N1 C4 C3 -177.83(19) . . . . ? C3 C4 C5 C6 -2.6(3) . . . . ? N1 C4 C5 C6 176.50(18) . . . . ? C4 C5 C6 C1 0.7(3) . . . . ? C2 C1 C6 C5 1.4(3) . . . . ? S1 C1 C6 C5 -173.03(16) . . . . ? C14 N2 C7 C8 -54.9(2) . . . . ? S1 N2 C7 C8 164.46(14) . . . . ? N2 C7 C8 C9 -52.7(3) . . . . ? N2 C7 C8 C13 129.5(2) . . . . ? C13 C8 C9 C10 -0.6(3) . . . . ? C7 C8 C9 C10 -178.5(2) . . . . ? C8 C9 C10 C11 1.3(4) . . . . ? C9 C10 C11 C12 -0.4(4) . . . . ? C10 C11 C12 C13 -1.3(4) . . . . ? C11 C12 C13 C8 2.0(3) . . . . ? C9 C8 C13 C12 -1.0(3) . . . . ? C7 C8 C13 C12 176.8(2) . . . . ? C7 N2 C14 C19 -48.0(3) . . . . ? S1 N2 C14 C19 92.1(2) . . . . ? C7 N2 C14 C15 124.9(2) . . . . ? S1 N2 C14 C15 -95.0(2) . . . . ? C19 C14 C15 C16 173.8(2) . . . . ? N2 C14 C15 C16 0.1(3) . . . . ? C19 C14 C15 C17 -2.8(2) . . . . ? N2 C14 C15 C17 -176.52(18) . . . . ? C16 C15 C17 C22 -59.8(3) . . . . ? C14 C15 C17 C22 116.8(2) . . . . ? C16 C15 C17 C18 -173.7(2) . . . . ? C14 C15 C17 C18 2.9(2) . . . . ? C15 C17 C18 O5 -124.48(19) . . . . ? C22 C17 C18 O5 116.1(2) . . . . ? C15 C17 C18 C19 -2.1(2) . . . . ? C22 C17 C18 C19 -121.54(18) . . . . ? C15 C17 C18 C20 116.43(19) . . . . ? C22 C17 C18 C20 -3.0(2) . . . . ? N2 C14 C19 C18 174.84(18) . . . . ? C15 C14 C19 C18 1.5(3) . . . . ? O5 C18 C19 C14 124.85(19) . . . . ? C20 C18 C19 C14 -113.0(2) . . . . ? C17 C18 C19 C14 0.5(2) . . . . ? O5 C18 C20 C21 -147.44(18) . . . . ? C19 C18 C20 C21 88.5(2) . . . . ? C17 C18 C20 C21 -24.2(2) . . . . ? C18 C20 C21 C22 42.3(2) . . . . ? C20 C21 C22 C17 -44.2(2) . . . . ? C15 C17 C22 C21 -85.0(2) . . . . ? C18 C17 C22 C21 28.9(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 O5 H5A O1 0.84 2.08 2.914(2) 174.6 3_666 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.80 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.256 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.052