# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 182/1221 data_sk002 _publ_contact_author ; Prof. Kari Rissanen ; _publ_contact_author_email 'kari.rissanen@jyu.fi' _publ_author_name 'Rissanen, Kari' _publ_requested_journal 'Chemical Communications' _audit_creation_method ? _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H24 O6, (C3 H5 N2)+ (Cl O4)-' _chemical_formula_sum 'C23 H29 Cl N2 O10' _chemical_formula_weight 528.93 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' 'O' 'O' 0.0106 0.0060 '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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 17.802(4) _cell_length_b 14.255(4) _cell_length_c 12.199(3) _cell_angle_alpha 90.00 _cell_angle_beta 129.34(1) _cell_angle_gamma 90.00 _cell_volume 2394(1) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(1) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8.01 _cell_measurement_theta_max 12.25 _exptl_crystal_description block _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.221 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_correction_T_min 0.9167 _exptl_absorpt_correction_T_max 0.9571 _exptl_absorpt_process_details ? _exptl_special_details ; Structure solution by direct methods ; _diffrn_ambient_temperature 173.0(1) _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 'Enraf-Nonius CAD4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2184 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0267 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2184 _reflns_number_gt 1887 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 (Enraf-Nonius, 1989)' _computing_cell_refinement 'CAD4 (Enraf-Nonius, 1989)' _computing_data_reduction 'XCAD4/WinGX-97 (Farrugia, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX-98 (Farrugia, 1998)' _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^)+(0.0405P)^2^+7.6190P] 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(14) _refine_ls_number_reflns 2184 _refine_ls_number_parameters 441 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1208 _refine_ls_wR_factor_gt 0.1150 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.181 _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 C2 C -0.0882(5) -0.2744(5) -0.2264(7) 0.0289(14) Uani 1 1 d . . . H2A H -0.063(5) -0.265(5) -0.285(7) 0.033(19) Uiso 1 1 d . . . H2B H -0.105(6) -0.209(5) -0.213(8) 0.04(2) Uiso 1 1 d . . . C3 C -0.0048(5) -0.3202(5) -0.0904(7) 0.0317(15) Uani 1 1 d . . . H3A H -0.022(5) -0.328(5) -0.025(7) 0.029(17) Uiso 1 1 d . . . H3B H 0.045(5) -0.283(5) -0.047(8) 0.04(2) Uiso 1 1 d . . . C5 C 0.1124(5) -0.4417(5) 0.0017(7) 0.0305(15) Uani 1 1 d . . . H5A H 0.168(6) -0.390(6) 0.051(9) 0.06(3) Uiso 1 1 d . . . H5B H 0.080(4) -0.458(4) 0.049(6) 0.019(15) Uiso 1 1 d . . . C6 C 0.1473(5) -0.5135(5) -0.0444(6) 0.0274(14) Uani 1 1 d . . . H6A H 0.212(6) -0.546(6) 0.041(9) 0.06(2) Uiso 1 1 d . . . H6B H 0.155(5) -0.484(4) -0.112(7) 0.022(16) Uiso 1 1 d . . . C8 C 0.0918(4) -0.6592(4) -0.1711(6) 0.0257(13) Uani 1 1 d . . . C9 C 0.1702(5) -0.6666(5) -0.1680(7) 0.0313(15) Uani 1 1 d . . . H9 H 0.217(5) -0.608(5) -0.121(7) 0.04(2) Uiso 1 1 d . . . C10 C 0.1790(5) -0.7438(5) -0.2266(7) 0.0342(16) Uani 1 1 d . . . H10 H 0.227(5) -0.756(5) -0.228(7) 0.028(18) Uiso 1 1 d . . . C11 C 0.1091(5) -0.8128(5) -0.2914(7) 0.0346(16) Uani 1 1 d . . . H11 H 0.108(5) -0.866(6) -0.339(8) 0.04(2) Uiso 1 1 d . . . C12 C 0.0292(5) -0.8057(5) -0.2975(7) 0.0314(15) Uani 1 1 d . . . H12 H -0.021(5) -0.857(5) -0.347(7) 0.028(17) Uiso 1 1 d . . . C13 C 0.0210(5) -0.7286(4) -0.2364(6) 0.0270(14) Uani 1 1 d . . . C15 C -0.1356(5) -0.7788(5) -0.3162(7) 0.0309(15) Uani 1 1 d . . . H15A H -0.155(4) -0.788(4) -0.410(6) 0.008(13) Uiso 1 1 d . . . H15B H -0.126(7) -0.844(6) -0.276(9) 0.06(3) Uiso 1 1 d . . . C16 C -0.2142(5) -0.7422(5) -0.3169(7) 0.0302(14) Uani 1 1 d . . . H16A H -0.188(4) -0.738(4) -0.220(6) 0.014(14) Uiso 1 1 d . . . H16B H -0.264(5) -0.789(5) -0.364(7) 0.032(18) Uiso 1 1 d . . . C18 C -0.3330(5) -0.6232(5) -0.4159(7) 0.0315(15) Uani 1 1 d . . . H18A H -0.383(4) -0.679(4) -0.465(6) 0.014(14) Uiso 1 1 d . . . H18B H -0.320(4) -0.604(4) -0.330(7) 0.020(15) Uiso 1 1 d . . . C19 C -0.3701(5) -0.5392(5) -0.5100(7) 0.0307(15) Uani 1 1 d . . . H19A H -0.440(5) -0.519(5) -0.550(7) 0.029(18) Uiso 1 1 d . . . H19B H -0.375(4) -0.548(4) -0.579(7) 0.006(14) Uiso 1 1 d . . . C21 C -0.3164(4) -0.3864(4) -0.5128(6) 0.0252(13) Uani 1 1 d . . . C22 C -0.3947(5) -0.3748(5) -0.6560(7) 0.0298(14) Uani 1 1 d . . . H22 H -0.447(6) -0.431(5) -0.717(8) 0.05(2) Uiso 1 1 d . . . C23 C -0.3997(5) -0.2947(5) -0.7267(7) 0.0332(15) Uani 1 1 d . . . H23 H -0.468(5) -0.294(5) -0.848(7) 0.032(18) Uiso 1 1 d . . . C24 C -0.3288(5) -0.2270(5) -0.6555(7) 0.0333(15) Uani 1 1 d . . . H24 H -0.325(5) -0.164(5) -0.703(7) 0.035(18) Uiso 1 1 d . . . C25 C -0.2495(5) -0.2384(5) -0.5109(7) 0.0320(15) Uani 1 1 d . . . H25 H -0.198(6) -0.195(5) -0.457(8) 0.04(2) Uiso 1 1 d . . . C26 C -0.2435(4) -0.3171(4) -0.4405(6) 0.0254(13) Uani 1 1 d . . . C28 C -0.1506(6) -0.5365(5) -0.4965(8) 0.0406(18) Uani 1 1 d . . . H28 H -0.191(5) -0.581(4) -0.493(6) 0.018(15) Uiso 1 1 d . . . C31 C -0.0517(6) -0.4246(6) -0.4494(9) 0.050(2) Uani 1 1 d . . . H31 H -0.003(6) -0.377(6) -0.394(8) 0.05(2) Uiso 1 1 d . . . C30 C -0.0991(6) -0.4467(5) -0.5828(8) 0.0374(17) Uani 1 1 d . . . H30 H -0.090(5) -0.432(5) -0.641(8) 0.033(18) Uiso 1 1 d . . . O1 O -0.1698(3) -0.3366(3) -0.2993(4) 0.0276(10) Uani 1 1 d . . . O4 O 0.0242(3) -0.4015(3) -0.1222(4) 0.0277(10) Uani 1 1 d . . . O7 O 0.0755(3) -0.5865(3) -0.1141(4) 0.0293(10) Uani 1 1 d . . . O14 O -0.0563(3) -0.7138(3) -0.2367(4) 0.0296(10) Uani 1 1 d . . . O17 O -0.2481(3) -0.6551(3) -0.3910(4) 0.0297(10) Uani 1 1 d . . . O20 O -0.3023(3) -0.4629(3) -0.4334(4) 0.0287(10) Uani 1 1 d . . . O100 O -0.1285(4) -0.0064(5) -0.4505(6) 0.0580(16) Uani 1 1 d . . . O101 O -0.0670(4) -0.1034(5) -0.5324(6) 0.0631(17) Uani 1 1 d . . . O102 O -0.2252(4) -0.0449(4) -0.6899(6) 0.0548(14) Uani 1 1 d . . . O103 O -0.0903(6) 0.0557(5) -0.5875(8) 0.080(2) Uani 1 1 d . . . N29 N -0.1610(4) -0.5175(4) -0.6117(6) 0.0377(14) Uani 1 1 d . . . H29 H -0.203(6) -0.552(5) -0.702(8) 0.04(2) Uiso 1 1 d . . . N27 N -0.0830(4) -0.4777(5) -0.3974(6) 0.0466(18) Uani 1 1 d . . . H27 H -0.069(6) -0.459(6) -0.313(9) 0.05(2) Uiso 1 1 d . . . Cl1 Cl -0.12799(11) -0.02396(11) -0.56607(15) 0.0330(4) Uani 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 C2 0.030(3) 0.026(3) 0.036(3) -0.008(3) 0.023(3) -0.008(3) C3 0.030(4) 0.036(4) 0.027(3) -0.015(3) 0.017(3) -0.015(3) C5 0.030(3) 0.035(4) 0.027(3) -0.003(3) 0.018(3) -0.008(3) C6 0.028(3) 0.031(3) 0.022(3) -0.003(3) 0.015(3) -0.004(3) C8 0.028(3) 0.025(3) 0.022(3) 0.005(2) 0.015(3) 0.006(3) C9 0.028(3) 0.040(4) 0.026(3) 0.011(3) 0.017(3) 0.007(3) C10 0.032(4) 0.042(4) 0.030(3) 0.010(3) 0.020(3) 0.018(3) C11 0.050(5) 0.030(4) 0.028(3) 0.007(3) 0.027(3) 0.011(3) C12 0.042(4) 0.030(4) 0.023(3) 0.005(3) 0.021(3) 0.003(3) C13 0.030(3) 0.028(3) 0.019(3) 0.002(2) 0.014(3) 0.004(3) C15 0.035(4) 0.027(4) 0.026(3) -0.007(3) 0.017(3) -0.014(3) C16 0.037(4) 0.027(3) 0.031(3) -0.002(3) 0.024(3) -0.009(3) C18 0.035(4) 0.034(4) 0.037(4) -0.010(3) 0.028(3) -0.010(3) C19 0.027(4) 0.036(4) 0.032(4) -0.013(3) 0.020(3) -0.009(3) C21 0.025(3) 0.029(3) 0.029(3) -0.006(3) 0.020(3) 0.001(3) C22 0.029(3) 0.030(3) 0.035(3) -0.006(3) 0.022(3) -0.001(3) C23 0.035(4) 0.041(4) 0.034(4) -0.001(3) 0.027(3) 0.005(3) C24 0.039(4) 0.034(4) 0.042(4) 0.005(3) 0.033(3) 0.009(3) C25 0.032(4) 0.033(4) 0.041(4) -0.002(3) 0.028(3) 0.004(3) C26 0.026(3) 0.026(3) 0.032(3) -0.002(3) 0.022(3) 0.003(3) C28 0.042(4) 0.038(4) 0.056(5) 0.011(3) 0.037(4) 0.010(3) C31 0.035(4) 0.047(5) 0.058(5) -0.029(4) 0.025(4) -0.010(4) C30 0.058(5) 0.029(4) 0.046(4) 0.007(3) 0.042(4) 0.008(3) O1 0.029(2) 0.027(2) 0.028(2) -0.0066(18) 0.019(2) -0.0037(19) O4 0.033(2) 0.028(2) 0.021(2) -0.0051(17) 0.0164(19) -0.0030(19) O7 0.031(2) 0.028(2) 0.030(2) -0.0061(19) 0.020(2) -0.0066(19) O14 0.031(2) 0.029(2) 0.030(2) -0.0095(19) 0.020(2) -0.008(2) O17 0.032(2) 0.033(2) 0.032(2) 0.0013(19) 0.024(2) -0.0030(19) O20 0.027(2) 0.026(2) 0.032(2) -0.0058(19) 0.018(2) -0.0065(19) O100 0.060(4) 0.077(4) 0.051(3) -0.015(3) 0.042(3) -0.004(3) O101 0.056(4) 0.067(4) 0.053(3) 0.005(3) 0.028(3) 0.027(3) O102 0.038(3) 0.065(4) 0.042(3) -0.005(3) 0.016(3) -0.003(3) O103 0.107(6) 0.062(4) 0.088(5) -0.016(4) 0.070(5) -0.042(4) N29 0.040(4) 0.042(3) 0.023(3) -0.007(3) 0.016(3) 0.004(3) N27 0.037(3) 0.079(5) 0.023(3) -0.006(3) 0.018(3) 0.017(4) Cl1 0.0329(8) 0.0345(8) 0.0332(8) -0.0033(8) 0.0218(7) -0.0027(8) _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 C2 O1 1.431(7) . ? C2 C3 1.503(10) . ? C3 O4 1.419(8) . ? C5 O4 1.439(8) . ? C5 C6 1.481(9) . ? C6 O7 1.436(8) . ? C8 C9 1.376(9) . ? C8 O7 1.377(8) . ? C8 C13 1.388(9) . ? C9 C10 1.375(10) . ? C10 C11 1.376(10) . ? C11 C12 1.380(10) . ? C12 C13 1.386(9) . ? C13 O14 1.389(8) . ? C15 O14 1.435(8) . ? C15 C16 1.488(10) . ? C16 O17 1.425(8) . ? C18 O17 1.415(8) . ? C18 C19 1.493(10) . ? C19 O20 1.443(8) . ? C21 O20 1.371(8) . ? C21 C22 1.391(9) . ? C21 C26 1.410(9) . ? C22 C23 1.400(10) . ? C23 C24 1.375(10) . ? C24 C25 1.405(10) . ? C25 C26 1.375(9) . ? C26 O1 1.379(7) . ? C28 N29 1.324(10) . ? C28 N27 1.329(10) . ? C31 C30 1.311(11) . ? C31 N27 1.319(11) . ? C30 N29 1.365(10) . ? O100 Cl1 1.437(5) . ? O101 Cl1 1.437(6) . ? O102 Cl1 1.432(5) . ? O103 Cl1 1.425(6) . ? 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 O1 C2 C3 108.7(5) . . ? O4 C3 C2 109.2(5) . . ? O4 C5 C6 108.6(5) . . ? O7 C6 C5 107.2(5) . . ? C9 C8 O7 125.3(6) . . ? C9 C8 C13 119.8(6) . . ? O7 C8 C13 114.9(5) . . ? C10 C9 C8 119.7(7) . . ? C9 C10 C11 120.7(7) . . ? C10 C11 C12 120.3(7) . . ? C11 C12 C13 119.0(7) . . ? C12 C13 C8 120.4(6) . . ? C12 C13 O14 124.1(6) . . ? C8 C13 O14 115.5(5) . . ? O14 C15 C16 107.3(6) . . ? O17 C16 C15 109.1(5) . . ? O17 C18 C19 108.4(5) . . ? O20 C19 C18 109.1(5) . . ? O20 C21 C22 124.8(6) . . ? O20 C21 C26 115.5(5) . . ? C22 C21 C26 119.6(6) . . ? C21 C22 C23 119.5(6) . . ? C24 C23 C22 120.6(6) . . ? C23 C24 C25 120.1(6) . . ? C26 C25 C24 119.8(7) . . ? C25 C26 O1 125.5(6) . . ? C25 C26 C21 120.3(6) . . ? O1 C26 C21 114.2(5) . . ? N29 C28 N27 105.9(7) . . ? C30 C31 N27 108.8(7) . . ? C31 C30 N29 106.2(7) . . ? C26 O1 C2 116.0(5) . . ? C3 O4 C5 112.5(5) . . ? C8 O7 C6 116.8(5) . . ? C13 O14 C15 116.9(5) . . ? C18 O17 C16 112.4(5) . . ? C21 O20 C19 116.0(5) . . ? C28 N29 C30 109.2(6) . . ? C31 N27 C28 109.8(6) . . ? O103 Cl1 O102 111.6(4) . . ? O103 Cl1 O100 109.7(4) . . ? O102 Cl1 O100 108.4(3) . . ? O103 Cl1 O101 108.8(5) . . ? O102 Cl1 O101 109.0(4) . . ? O100 Cl1 O101 109.3(4) . . ? 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 O1 C2 C3 O4 65.0(7) . . . . ? O4 C5 C6 O7 -64.0(6) . . . . ? O7 C8 C9 C10 178.8(6) . . . . ? C13 C8 C9 C10 -1.6(9) . . . . ? C8 C9 C10 C11 1.5(9) . . . . ? C9 C10 C11 C12 -0.4(10) . . . . ? C10 C11 C12 C13 -0.6(9) . . . . ? C11 C12 C13 C8 0.5(9) . . . . ? C11 C12 C13 O14 179.6(6) . . . . ? C9 C8 C13 C12 0.5(9) . . . . ? O7 C8 C13 C12 -179.8(5) . . . . ? C9 C8 C13 O14 -178.6(5) . . . . ? O7 C8 C13 O14 1.0(7) . . . . ? O14 C15 C16 O17 64.2(7) . . . . ? O17 C18 C19 O20 -67.6(7) . . . . ? O20 C21 C22 C23 -178.1(6) . . . . ? C26 C21 C22 C23 0.5(9) . . . . ? C21 C22 C23 C24 -1.0(9) . . . . ? C22 C23 C24 C25 1.0(10) . . . . ? C23 C24 C25 C26 -0.5(9) . . . . ? C24 C25 C26 O1 179.9(6) . . . . ? C24 C25 C26 C21 0.1(9) . . . . ? O20 C21 C26 C25 178.7(5) . . . . ? C22 C21 C26 C25 -0.1(9) . . . . ? O20 C21 C26 O1 -1.2(7) . . . . ? C22 C21 C26 O1 -180.0(5) . . . . ? N27 C31 C30 N29 -0.9(9) . . . . ? C25 C26 O1 C2 -7.7(8) . . . . ? C21 C26 O1 C2 172.2(5) . . . . ? C3 C2 O1 C26 -163.9(5) . . . . ? C2 C3 O4 C5 171.6(5) . . . . ? C6 C5 O4 C3 -168.9(5) . . . . ? C9 C8 O7 C6 -0.9(8) . . . . ? C13 C8 O7 C6 179.5(5) . . . . ? C5 C6 O7 C8 177.3(5) . . . . ? C12 C13 O14 C15 -5.5(8) . . . . ? C8 C13 O14 C15 173.6(5) . . . . ? C16 C15 O14 C13 -172.7(5) . . . . ? C19 C18 O17 C16 -172.6(5) . . . . ? C15 C16 O17 C18 170.6(5) . . . . ? C22 C21 O20 C19 5.8(8) . . . . ? C26 C21 O20 C19 -172.9(5) . . . . ? C18 C19 O20 C21 168.2(5) . . . . ? N27 C28 N29 C30 0.1(8) . . . . ? C31 C30 N29 C28 0.5(8) . . . . ? C30 C31 N27 C28 1.0(9) . . . . ? N29 C28 N27 C31 -0.7(8) . . . . ? 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 N29 H29 O20 0.99(8) 2.19(8) 3.048(7) 144(6) 2_544 N29 H29 O1 0.99(8) 2.28(8) 3.022(7) 132(6) 2_544 N27 H27 O4 0.94(9) 1.99(9) 2.823(7) 148(7) . N27 H27 O1 0.94(9) 2.58(8) 3.195(7) 124(6) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.243 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.062 # = end data_sak009 _audit_creation_method ? _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'c20 H24 O6, (C3 H5 N2)+, (Cl O4)-' _chemical_formula_sum 'C23 H29 Cl N2 O10' _chemical_formula_weight 528.93 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' 'O' 'O' 0.0106 0.0060 '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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 17.804(1) _cell_length_b 14.131(1) _cell_length_c 12.317(1) _cell_angle_alpha 90.00 _cell_angle_beta 129.003(3) _cell_angle_gamma 90.00 _cell_volume 2408.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(1) _cell_measurement_reflns_used 1342 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9075 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(1) _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 'Nonius KappaCCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2828 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0890 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.87 _reflns_number_total 2828 _reflns_number_gt 1953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'Denzo-SMN v0.93.0 (Otwinowki, 1997)' _computing_data_reduction 'Denzo-SMN v0.93.0 (Otwinowki, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX-98 (Farrugia, 1998)' _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^)+(0.1138P)^2^+10.7147P] 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 SHELXL _refine_ls_extinction_coef 0.0076(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(2) _refine_ls_number_reflns 2828 _refine_ls_number_parameters 326 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0887 _refine_ls_wR_factor_ref 0.2535 _refine_ls_wR_factor_gt 0.2289 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _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 Cl1 Cl -0.22851(16) -0.02106(17) -0.4899(2) 0.0387(6) Uani 1 1 d . . . C2 C 0.0213(7) 0.0347(7) 0.0507(11) 0.034(2) Uani 1 1 d . . . H2A H -0.0435 0.0167 0.0187 0.041 Uiso 1 1 calc R . . H2B H 0.0161 0.0500 -0.0322 0.041 Uiso 1 1 calc R . . C3 C 0.0584(7) 0.1177(7) 0.1457(11) 0.036(2) Uani 1 1 d . . . H3A H 0.0090 0.1684 0.1017 0.043 Uiso 1 1 calc R . . H3B H 0.0723 0.0993 0.2343 0.043 Uiso 1 1 calc R . . C5 C 0.1790(7) 0.2387(8) 0.2520(10) 0.038(2) Uani 1 1 d . . . H5A H 0.2022 0.2271 0.3480 0.045 Uiso 1 1 calc R . . H5B H 0.1261 0.2857 0.2067 0.045 Uiso 1 1 calc R . . C6 C 0.2595(7) 0.2749(7) 0.2566(11) 0.034(2) Uani 1 1 d . . . H6A H 0.2384 0.2803 0.1609 0.040 Uiso 1 1 calc R . . H6B H 0.2802 0.3381 0.3011 0.040 Uiso 1 1 calc R . . C8 C 0.4141(7) 0.2213(7) 0.3374(10) 0.035(2) Uani 1 1 d . . . C9 C 0.4229(7) 0.2971(7) 0.2755(10) 0.036(2) Uani 1 1 d . . . H9 H 0.3742 0.3445 0.2286 0.043 Uiso 1 1 calc R . . C10 C 0.5050(7) 0.3035(7) 0.2828(11) 0.041(2) Uani 1 1 d . . . H10 H 0.5118 0.3555 0.2407 0.049 Uiso 1 1 calc R . . C11 C 0.5741(8) 0.2357(8) 0.3498(10) 0.040(2) Uani 1 1 d . . . H11 H 0.6290 0.2403 0.3535 0.048 Uiso 1 1 calc R . . C12 C 0.5661(7) 0.1593(8) 0.4131(11) 0.040(2) Uani 1 1 d . . . H12 H 0.6154 0.1126 0.4609 0.048 Uiso 1 1 calc R . . C13 C 0.4851(7) 0.1521(7) 0.4056(9) 0.032(2) Uani 1 1 d . . . C15 C 0.5398(7) 0.0067(8) 0.5331(11) 0.041(2) Uani 1 1 d . . . H15A H 0.6031 0.0305 0.6164 0.049 Uiso 1 1 calc R . . H15B H 0.5484 -0.0205 0.4674 0.049 Uiso 1 1 calc R . . C16 C 0.5007(7) -0.0671(8) 0.5746(10) 0.037(2) Uani 1 1 d . . . H16A H 0.5485 -0.1185 0.6284 0.045 Uiso 1 1 calc R . . H16B H 0.4868 -0.0383 0.6336 0.045 Uiso 1 1 calc R . . C18 C 0.3822(8) -0.1892(7) 0.4725(10) 0.037(2) Uani 1 1 d . . . H18A H 0.3595 -0.1745 0.5262 0.044 Uiso 1 1 calc R . . H18B H 0.4368 -0.2342 0.5277 0.044 Uiso 1 1 calc R . . C19 C 0.3024(7) -0.2325(7) 0.3363(11) 0.037(2) Uani 1 1 d . . . H19A H 0.3237 -0.2435 0.2799 0.045 Uiso 1 1 calc R . . H19B H 0.2842 -0.2942 0.3518 0.045 Uiso 1 1 calc R . . C21 C 0.1487(6) -0.1882(7) 0.1231(10) 0.031(2) Uani 1 1 d . . . C22 C 0.1432(7) -0.2680(7) 0.0522(11) 0.037(2) Uani 1 1 d . . . H22 H 0.1913 -0.3158 0.1013 0.044 Uiso 1 1 calc R . . C23 C 0.0686(7) -0.2781(7) -0.0890(11) 0.038(2) Uani 1 1 d . . . H23 H 0.0664 -0.3320 -0.1371 0.045 Uiso 1 1 calc R . . C24 C -0.0021(7) -0.2113(7) -0.1599(11) 0.039(2) Uani 1 1 d . . . H24 H -0.0541 -0.2192 -0.2568 0.047 Uiso 1 1 calc R . . C25 C 0.0018(7) -0.1309(7) -0.0901(10) 0.035(2) Uani 1 1 d . . . H25 H -0.0476 -0.0844 -0.1398 0.042 Uiso 1 1 calc R . . C26 C 0.0758(7) -0.1191(6) 0.0483(10) 0.030(2) Uani 1 1 d . . . O1 O 0.0882(5) -0.0416(5) 0.1277(7) 0.0345(15) Uani 1 1 d . . . O4 O 0.1449(5) 0.1518(5) 0.1736(7) 0.0342(15) Uani 1 1 d . . . O7 O 0.3375(5) 0.2084(5) 0.3368(7) 0.0342(15) Uani 1 1 d . . . O14 O 0.4697(4) 0.0825(5) 0.4668(7) 0.0340(15) Uani 1 1 d . . . O17 O 0.4134(4) -0.1042(5) 0.4482(6) 0.0349(15) Uani 1 1 d . . . O20 O 0.2209(4) -0.1695(5) 0.2635(7) 0.0340(15) Uani 1 1 d . . . O101 O -0.1703(7) -0.1039(7) -0.4602(10) 0.067(3) Uani 1 1 d . . . O102 O -0.3242(6) -0.0400(8) -0.6176(9) 0.067(3) Uani 1 1 d . . . O103 O -0.2331(6) -0.0065(6) -0.3812(8) 0.049(2) Uani 1 1 d . . . O104 O -0.1869(9) 0.0573(7) -0.5056(12) 0.079(3) Uani 1 1 d . . . C30 C 0.2752(9) -0.0313(8) -0.0094(12) 0.046(3) Uani 1 1 d . . . H30 H 0.2736 -0.0515 -0.0844 0.056 Uiso 1 1 calc R . . C29 C 0.2209(7) 0.0366(8) -0.0144(11) 0.038(2) Uani 1 1 d . . . H29 H 0.1752 0.0750 -0.0929 0.046 Uiso 1 1 calc R . . C31 C 0.3324(7) -0.0656(8) 0.1214(11) 0.039(2) Uani 1 1 d . . . H31 H 0.3803 -0.1131 0.1560 0.047 Uiso 1 1 calc R . . N27 N 0.3116(6) -0.0234(6) 0.1925(8) 0.0342(18) Uani 1 1 d . . . H27 H 0.3385 -0.0346 0.2804 0.041 Uiso 1 1 calc R . . N28 N 0.2418(5) 0.0408(6) 0.1094(8) 0.0326(18) Uani 1 1 d . . . H28 H 0.2149 0.0787 0.1331 0.039 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 Cl1 0.0385(11) 0.0368(12) 0.0422(14) -0.0013(12) 0.0261(11) -0.0014(11) C2 0.031(5) 0.033(5) 0.037(5) 0.004(4) 0.020(4) 0.002(4) C3 0.039(5) 0.037(5) 0.042(6) 0.006(4) 0.030(5) 0.010(4) C5 0.028(4) 0.045(6) 0.031(5) 0.002(4) 0.015(4) 0.009(4) C6 0.046(5) 0.020(5) 0.041(5) 0.006(4) 0.030(5) 0.007(4) C8 0.034(5) 0.041(6) 0.031(5) -0.002(4) 0.021(4) 0.002(4) C9 0.035(5) 0.033(5) 0.031(5) -0.006(4) 0.016(4) -0.006(4) C10 0.043(6) 0.025(5) 0.037(6) -0.006(4) 0.016(5) -0.010(4) C11 0.039(5) 0.054(7) 0.030(5) -0.013(5) 0.023(5) -0.016(5) C12 0.029(5) 0.043(6) 0.036(5) -0.007(4) 0.015(4) -0.002(4) C13 0.032(4) 0.043(6) 0.022(4) -0.007(4) 0.018(4) -0.002(4) C15 0.027(4) 0.041(6) 0.036(5) 0.010(5) 0.011(4) 0.017(4) C16 0.035(5) 0.043(6) 0.028(5) 0.007(4) 0.017(4) 0.008(4) C18 0.051(6) 0.035(5) 0.035(5) 0.020(4) 0.032(5) 0.015(4) C19 0.038(5) 0.036(6) 0.046(6) 0.008(5) 0.031(5) 0.011(4) C21 0.031(4) 0.030(5) 0.043(6) 0.002(4) 0.029(5) 0.003(4) C22 0.038(5) 0.039(5) 0.045(6) 0.001(4) 0.031(5) -0.006(4) C23 0.048(6) 0.036(5) 0.046(6) -0.005(5) 0.037(5) -0.009(4) C24 0.043(5) 0.038(6) 0.036(5) -0.005(4) 0.025(5) -0.010(5) C25 0.039(5) 0.039(5) 0.036(5) 0.007(4) 0.027(5) -0.004(4) C26 0.034(4) 0.021(4) 0.035(5) -0.004(4) 0.021(4) -0.007(4) O1 0.038(3) 0.028(4) 0.036(4) 0.010(3) 0.022(3) 0.008(3) O4 0.040(3) 0.037(4) 0.039(4) 0.005(3) 0.031(3) 0.008(3) O7 0.037(3) 0.031(4) 0.036(4) 0.005(3) 0.024(3) 0.006(3) O14 0.026(3) 0.033(4) 0.032(4) 0.005(3) 0.013(3) 0.005(3) O17 0.031(3) 0.032(4) 0.028(3) 0.008(3) 0.011(3) 0.003(3) O20 0.027(3) 0.034(4) 0.032(3) 0.005(3) 0.014(3) 0.005(3) O101 0.062(5) 0.063(6) 0.069(6) 0.007(5) 0.038(5) 0.025(4) O102 0.035(4) 0.083(7) 0.042(5) -0.006(4) 0.005(4) 0.002(4) O103 0.059(5) 0.059(5) 0.050(5) -0.003(4) 0.044(4) -0.003(4) O104 0.109(8) 0.062(6) 0.094(8) -0.007(6) 0.077(7) -0.030(6) C30 0.061(7) 0.047(6) 0.045(7) -0.014(5) 0.040(6) -0.010(6) C29 0.035(5) 0.048(6) 0.031(5) 0.011(4) 0.020(4) 0.005(4) C31 0.039(5) 0.042(6) 0.049(6) 0.005(5) 0.034(5) 0.002(4) N27 0.034(4) 0.045(5) 0.022(4) 0.005(4) 0.017(3) 0.000(4) N28 0.036(4) 0.034(4) 0.040(5) -0.003(3) 0.030(4) 0.002(3) _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 Cl1 O103 1.407(7) . ? Cl1 O104 1.411(9) . ? Cl1 O102 1.441(8) . ? Cl1 O101 1.450(9) . ? C2 O1 1.434(11) . ? C2 C3 1.486(14) . ? C3 O4 1.432(12) . ? C5 O4 1.438(13) . ? C5 C6 1.488(14) . ? C6 O7 1.436(11) . ? C8 O7 1.371(11) . ? C8 C9 1.379(14) . ? C8 C13 1.386(14) . ? C9 C10 1.409(15) . ? C10 C11 1.356(15) . ? C11 C12 1.391(16) . ? C12 C13 1.390(13) . ? C13 O14 1.367(12) . ? C15 O14 1.445(11) . ? C15 C16 1.512(16) . ? C16 O17 1.438(12) . ? C18 O17 1.433(12) . ? C18 C19 1.486(15) . ? C19 O20 1.437(11) . ? C21 O20 1.384(12) . ? C21 C22 1.391(14) . ? C21 C26 1.408(13) . ? C22 C23 1.379(15) . ? C23 C24 1.362(15) . ? C24 C25 1.399(15) . ? C25 C26 1.358(13) . ? C26 O1 1.391(11) . ? C30 C29 1.336(15) . ? C30 C31 1.343(16) . ? C29 N28 1.324(12) . ? C31 N27 1.292(13) . ? N27 N28 1.347(11) . ? 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 O103 Cl1 O104 111.5(6) . . ? O103 Cl1 O102 109.2(5) . . ? O104 Cl1 O102 110.9(7) . . ? O103 Cl1 O101 109.8(6) . . ? O104 Cl1 O101 108.3(6) . . ? O102 Cl1 O101 107.0(6) . . ? O1 C2 C3 107.4(8) . . ? O4 C3 C2 109.5(7) . . ? O4 C5 C6 108.0(8) . . ? O7 C6 C5 107.1(7) . . ? O7 C8 C9 123.9(9) . . ? O7 C8 C13 115.7(8) . . ? C9 C8 C13 120.4(9) . . ? C8 C9 C10 119.2(9) . . ? C11 C10 C9 120.1(10) . . ? C10 C11 C12 121.0(10) . . ? C13 C12 C11 119.2(10) . . ? O14 C13 C8 114.9(8) . . ? O14 C13 C12 125.1(9) . . ? C8 C13 C12 120.0(9) . . ? O14 C15 C16 106.5(8) . . ? O17 C16 C15 107.4(8) . . ? O17 C18 C19 109.3(7) . . ? O20 C19 C18 108.7(8) . . ? O20 C21 C22 125.6(8) . . ? O20 C21 C26 115.7(8) . . ? C22 C21 C26 118.7(9) . . ? C23 C22 C21 120.4(10) . . ? C24 C23 C22 120.3(10) . . ? C23 C24 C25 120.0(10) . . ? C26 C25 C24 120.3(10) . . ? C25 C26 O1 125.4(9) . . ? C25 C26 C21 120.2(9) . . ? O1 C26 C21 114.4(8) . . ? C26 O1 C2 115.4(7) . . ? C3 O4 C5 112.6(7) . . ? C8 O7 C6 116.5(7) . . ? C13 O14 C15 116.3(7) . . ? C18 O17 C16 112.1(7) . . ? C21 O20 C19 116.1(7) . . ? C29 C30 C31 107.1(9) . . ? N28 C29 C30 108.0(9) . . ? N27 C31 C30 108.8(10) . . ? C31 N27 N28 108.5(8) . . ? C29 N28 N27 107.5(8) . . ? 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 O1 C2 C3 O4 68.8(10) . . . . ? O4 C5 C6 O7 -66.0(10) . . . . ? O7 C8 C9 C10 179.8(9) . . . . ? C13 C8 C9 C10 -0.1(14) . . . . ? C8 C9 C10 C11 0.1(14) . . . . ? C9 C10 C11 C12 -0.5(15) . . . . ? C10 C11 C12 C13 0.9(15) . . . . ? O7 C8 C13 O14 -2.2(12) . . . . ? C9 C8 C13 O14 177.8(8) . . . . ? O7 C8 C13 C12 -179.4(8) . . . . ? C9 C8 C13 C12 0.6(14) . . . . ? C11 C12 C13 O14 -177.8(9) . . . . ? C11 C12 C13 C8 -0.9(14) . . . . ? O14 C15 C16 O17 65.0(10) . . . . ? O17 C18 C19 O20 -64.5(9) . . . . ? O20 C21 C22 C23 -178.7(8) . . . . ? C26 C21 C22 C23 1.1(13) . . . . ? C21 C22 C23 C24 -1.8(14) . . . . ? C22 C23 C24 C25 1.2(14) . . . . ? C23 C24 C25 C26 0.0(14) . . . . ? C24 C25 C26 O1 178.6(9) . . . . ? C24 C25 C26 C21 -0.7(13) . . . . ? O20 C21 C26 C25 179.9(8) . . . . ? C22 C21 C26 C25 0.2(13) . . . . ? O20 C21 C26 O1 0.6(11) . . . . ? C22 C21 C26 O1 -179.2(8) . . . . ? C25 C26 O1 C2 -6.4(12) . . . . ? C21 C26 O1 C2 173.0(7) . . . . ? C3 C2 O1 C26 -167.7(7) . . . . ? C2 C3 O4 C5 173.4(8) . . . . ? C6 C5 O4 C3 -171.7(8) . . . . ? C9 C8 O7 C6 5.2(13) . . . . ? C13 C8 O7 C6 -174.9(8) . . . . ? C5 C6 O7 C8 171.0(8) . . . . ? C8 C13 O14 C15 177.1(8) . . . . ? C12 C13 O14 C15 -5.9(13) . . . . ? C16 C15 O14 C13 -172.4(8) . . . . ? C19 C18 O17 C16 -170.3(8) . . . . ? C15 C16 O17 C18 166.4(8) . . . . ? C22 C21 O20 C19 8.1(12) . . . . ? C26 C21 O20 C19 -171.6(8) . . . . ? C18 C19 O20 C21 165.9(7) . . . . ? C31 C30 C29 N28 -2.5(13) . . . . ? C29 C30 C31 N27 2.4(13) . . . . ? C30 C31 N27 N28 -1.4(12) . . . . ? C30 C29 N28 N27 1.7(11) . . . . ? C31 N27 N28 C29 -0.2(11) . . . . ? 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 N27 H27 O17 0.88 1.88 2.706(10) 154.9 . N27 H27 O14 0.88 2.59 3.099(10) 117.6 . N28 H28 O4 0.88 1.91 2.789(9) 173.8 . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.780 _refine_diff_density_min -0.493 _refine_diff_density_rms 0.147