# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2000 # CCDC Number: 440/156 data_comp15 _audit_creation_method ? _publ_contact_author ; Prof. Kari Rissanen ; _publ_contact_author_email 'krissane@cc.jyu.fi' _publ_author_name ; Kiviniemi, Sari Nissinen Maija Lms, Markku Rissanen, Kari Pursiainen Jouni ; _publ_requested_journal 'New Journal of Chemistry' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '225-228' _chemical_formula_moiety 'C20 H24 O6, (C2 H4 N3)+ (Cl O4)-' _chemical_formula_sum 'C22 H28 Cl N3 O10' _chemical_formula_weight 529.92 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 'C c' 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 17.7939(9) _cell_length_b 14.3421(9) _cell_length_c 11.9338(5) _cell_angle_alpha 90.00 _cell_angle_beta 129.008(2) _cell_angle_gamma 90.00 _cell_volume 2366.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.225 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.8583 _exptl_absorpt_correction_T_max 0.9778 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 '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 2800 _diffrn_reflns_av_R_equivalents 0.084 _diffrn_reflns_av_sigmaI/netI 0.0703 _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 -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.85 _reflns_number_total 2800 _reflns_number_gt 2327 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'Shelxs-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0487P)^2^+6.3211P] 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 -0.02(14) _refine_ls_number_reflns 2800 _refine_ls_number_parameters 325 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0810 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1552 _refine_ls_wR_factor_gt 0.1460 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _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 0.03708(10) 0.02040(10) 0.15730(14) 0.0328(3) Uani 1 1 d . . . C2 C 0.0310(4) 0.7786(4) 0.4068(7) 0.0305(13) Uani 1 1 d . . . H2A H 0.0063 0.7855 0.3062 0.037 Uiso 1 1 calc R . . H2B H 0.0536 0.8402 0.4546 0.037 Uiso 1 1 calc R . . C3 C -0.0472(4) 0.7419(4) 0.4090(7) 0.0295(13) Uani 1 1 d . . . H3A H -0.0217 0.7336 0.5098 0.035 Uiso 1 1 calc R . . H3B H -0.1016 0.7867 0.3609 0.035 Uiso 1 1 calc R . . C5 C -0.1638(4) 0.6224(4) 0.3128(7) 0.0304(13) Uani 1 1 d . . . H5A H -0.2135 0.6721 0.2671 0.036 Uiso 1 1 calc R . . H5B H -0.1477 0.6062 0.4064 0.036 Uiso 1 1 calc R . . C6 C -0.2020(4) 0.5383(4) 0.2171(7) 0.0294(13) Uani 1 1 d . . . H6A H -0.2655 0.5203 0.1890 0.035 Uiso 1 1 calc R . . H6B H -0.2107 0.5525 0.1284 0.035 Uiso 1 1 calc R . . C8 C -0.1500(4) 0.3863(4) 0.2124(6) 0.0222(11) Uani 1 1 d . . . C9 C -0.2296(4) 0.3736(4) 0.0697(6) 0.0284(12) Uani 1 1 d . . . H9 H -0.2795 0.4192 0.0206 0.034 Uiso 1 1 calc R . . C10 C -0.2363(4) 0.2923(5) -0.0025(6) 0.0322(13) Uani 1 1 d . . . H10 H -0.2900 0.2838 -0.1015 0.039 Uiso 1 1 calc R . . C11 C -0.1652(4) 0.2250(4) 0.0699(6) 0.0299(13) Uani 1 1 d . . . H11 H -0.1706 0.1702 0.0206 0.036 Uiso 1 1 calc R . . C12 C -0.0856(4) 0.2368(4) 0.2145(6) 0.0278(12) Uani 1 1 d . . . H12 H -0.0371 0.1901 0.2643 0.033 Uiso 1 1 calc R . . C13 C -0.0780(4) 0.3176(4) 0.2855(6) 0.0209(10) Uani 1 1 d . . . C15 C 0.0806(4) 0.2766(4) 0.4993(7) 0.0271(12) Uani 1 1 d . . . H15A H 0.0986 0.2660 0.4369 0.033 Uiso 1 1 calc R . . H15B H 0.0650 0.2156 0.5191 0.033 Uiso 1 1 calc R . . C16 C 0.1625(4) 0.3215(4) 0.6374(6) 0.0270(12) Uani 1 1 d . . . H16A H 0.1432 0.3348 0.6976 0.032 Uiso 1 1 calc R . . H16B H 0.2189 0.2790 0.6918 0.032 Uiso 1 1 calc R . . C18 C 0.2783(4) 0.4448(4) 0.7295(6) 0.0282(12) Uani 1 1 d . . . H18A H 0.3268 0.3945 0.7836 0.034 Uiso 1 1 calc R . . H18B H 0.2691 0.4753 0.7945 0.034 Uiso 1 1 calc R . . C19 C 0.3125(4) 0.5144(4) 0.6776(6) 0.0281(12) Uani 1 1 d . . . H19A H 0.3754 0.5411 0.7600 0.034 Uiso 1 1 calc R . . H19B H 0.3207 0.4846 0.6111 0.034 Uiso 1 1 calc R . . C21 C 0.2566(4) 0.6601(4) 0.5488(6) 0.0242(11) Uani 1 1 d . . . C22 C 0.3353(4) 0.6685(4) 0.5527(6) 0.0280(12) Uani 1 1 d . . . H22 H 0.3826 0.6204 0.5942 0.034 Uiso 1 1 calc R . . C23 C 0.3456(5) 0.7474(5) 0.4957(6) 0.0325(13) Uani 1 1 d . . . H23 H 0.4008 0.7544 0.5009 0.039 Uiso 1 1 calc R . . C24 C 0.2754(4) 0.8153(5) 0.4319(6) 0.0313(13) Uani 1 1 d . . . H24 H 0.2822 0.8684 0.3913 0.038 Uiso 1 1 calc R . . C25 C 0.1955(5) 0.8082(4) 0.4253(6) 0.0303(13) Uani 1 1 d . . . H25 H 0.1483 0.8563 0.3825 0.036 Uiso 1 1 calc R . . C26 C 0.1851(4) 0.7290(4) 0.4827(6) 0.0249(12) Uani 1 1 d . . . C29 C 0.0725(4) 0.4439(4) 0.1439(6) 0.0293(12) Uani 1 1 d . . . H29 H 0.0798 0.4186 0.0777 0.035 Uiso 1 1 calc R . . C31 C 0.0219(5) 0.5299(4) 0.2328(7) 0.0294(13) Uani 1 1 d . . . H31 H -0.0112 0.5748 0.2459 0.035 Uiso 1 1 calc R . . O1 O 0.1086(3) 0.7128(3) 0.4823(4) 0.0280(9) Uani 1 1 d . . . O4 O -0.0799(3) 0.6544(3) 0.3350(4) 0.0264(9) Uani 1 1 d . . . O7 O -0.1346(3) 0.4636(3) 0.2936(4) 0.0243(8) Uani 1 1 d . . . O14 O -0.0026(3) 0.3381(3) 0.4276(4) 0.0242(8) Uani 1 1 d . . . O17 O 0.1879(3) 0.4066(3) 0.6056(4) 0.0267(8) Uani 1 1 d . . . O20 O 0.2399(3) 0.5862(3) 0.6041(4) 0.0270(9) Uani 1 1 d . . . O101 O 0.0369(4) 0.0025(4) 0.2743(6) 0.0548(14) Uani 1 1 d . . . O102 O 0.1020(4) 0.0960(5) 0.1937(6) 0.0681(18) Uani 1 1 d . . . O103 O -0.0581(4) 0.0471(4) 0.0332(6) 0.0564(14) Uani 1 1 d . . . O104 O 0.0687(6) -0.0594(5) 0.1282(8) 0.086(2) Uani 1 1 d . . . N27 N 0.0874(3) 0.4703(4) 0.3291(5) 0.0275(10) Uani 1 1 d . . . H27 H 0.1080 0.4665 0.4180 0.033 Uiso 1 1 calc R . . N28 N 0.1191(4) 0.4159(4) 0.2749(6) 0.0333(11) Uani 1 1 d . . . N30 N 0.0111(3) 0.5152(4) 0.1136(5) 0.0301(11) Uani 1 1 d . . . H30 H -0.0279 0.5453 0.0313 0.036 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 0.0311(7) 0.0329(7) 0.0333(7) 0.0044(7) 0.0196(6) 0.0031(7) C2 0.033(3) 0.021(3) 0.028(3) 0.001(2) 0.015(3) 0.001(2) C3 0.035(3) 0.020(3) 0.036(3) -0.005(2) 0.023(3) 0.003(2) C5 0.037(3) 0.024(3) 0.040(3) 0.002(2) 0.029(3) 0.003(3) C6 0.023(3) 0.026(3) 0.033(3) 0.006(2) 0.015(3) 0.007(2) C8 0.026(3) 0.021(3) 0.025(3) 0.006(2) 0.019(2) 0.004(2) C9 0.025(3) 0.032(3) 0.025(3) 0.000(2) 0.014(2) -0.005(2) C10 0.031(3) 0.038(3) 0.027(3) -0.005(3) 0.018(3) -0.013(3) C11 0.037(3) 0.029(3) 0.033(3) -0.007(2) 0.027(3) -0.010(3) C12 0.028(3) 0.023(3) 0.035(3) 0.003(2) 0.021(3) 0.000(2) C13 0.021(3) 0.020(3) 0.023(2) -0.002(2) 0.014(2) -0.005(2) C15 0.029(3) 0.019(3) 0.035(3) 0.005(2) 0.021(3) 0.005(2) C16 0.032(3) 0.024(3) 0.026(3) 0.009(2) 0.019(3) 0.004(2) C18 0.024(3) 0.028(3) 0.024(3) 0.000(2) 0.011(2) 0.003(2) C19 0.023(3) 0.028(3) 0.029(3) 0.005(2) 0.014(2) 0.003(2) C21 0.028(3) 0.022(3) 0.021(3) -0.004(2) 0.015(2) -0.007(2) C22 0.025(3) 0.032(3) 0.028(3) -0.006(2) 0.017(3) -0.004(2) C23 0.034(3) 0.039(3) 0.025(3) -0.010(3) 0.019(3) -0.017(3) C24 0.040(4) 0.031(3) 0.026(3) -0.005(2) 0.022(3) -0.009(3) C25 0.039(3) 0.026(3) 0.022(3) -0.003(2) 0.017(3) -0.006(3) C26 0.033(3) 0.023(3) 0.019(2) -0.006(2) 0.016(2) -0.011(2) C29 0.037(3) 0.025(3) 0.031(3) -0.001(2) 0.024(3) -0.003(3) C31 0.038(3) 0.025(3) 0.034(3) 0.001(2) 0.027(3) 0.000(3) O1 0.030(2) 0.025(2) 0.030(2) 0.0080(17) 0.0193(19) 0.0058(17) O4 0.030(2) 0.021(2) 0.035(2) -0.0043(16) 0.0237(19) -0.0006(16) O7 0.027(2) 0.0187(19) 0.0254(19) 0.0017(15) 0.0155(17) 0.0033(16) O14 0.0215(19) 0.026(2) 0.0207(18) 0.0012(15) 0.0113(16) 0.0041(16) O17 0.029(2) 0.024(2) 0.0200(18) 0.0034(15) 0.0126(18) -0.0013(16) O20 0.025(2) 0.026(2) 0.029(2) 0.0048(17) 0.0160(19) 0.0025(17) O101 0.060(3) 0.072(4) 0.049(3) 0.015(3) 0.042(3) 0.010(3) O102 0.054(3) 0.082(5) 0.057(4) -0.002(3) 0.029(3) -0.031(3) O103 0.036(3) 0.068(4) 0.043(3) 0.011(3) 0.014(2) 0.010(3) O104 0.136(7) 0.061(4) 0.076(4) 0.013(4) 0.074(5) 0.047(5) N27 0.029(3) 0.033(3) 0.021(2) 0.001(2) 0.016(2) -0.003(2) N28 0.040(3) 0.034(3) 0.033(3) 0.003(2) 0.026(3) 0.003(2) N30 0.032(3) 0.036(3) 0.021(2) 0.005(2) 0.016(2) 0.002(2) _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 O104 1.412(6) . ? Cl1 O101 1.421(5) . ? Cl1 O103 1.432(5) . ? Cl1 O102 1.437(6) . ? C2 O1 1.429(7) . ? C2 C3 1.503(9) . ? C3 O4 1.430(7) . ? C5 O4 1.419(7) . ? C5 C6 1.498(9) . ? C6 O7 1.428(7) . ? C8 C9 1.380(8) . ? C8 O7 1.382(7) . ? C8 C13 1.402(8) . ? C9 C10 1.411(9) . ? C10 C11 1.378(9) . ? C11 C12 1.392(8) . ? C12 C13 1.390(8) . ? C13 O14 1.378(6) . ? C15 O14 1.451(6) . ? C15 C16 1.494(9) . ? C16 O17 1.433(7) . ? C18 O17 1.442(7) . ? C18 C19 1.491(8) . ? C19 O20 1.440(7) . ? C21 O20 1.377(7) . ? C21 C22 1.377(8) . ? C21 C26 1.398(8) . ? C22 C23 1.390(9) . ? C23 C24 1.375(9) . ? C24 C25 1.378(9) . ? C25 C26 1.397(8) . ? C26 O1 1.379(7) . ? C29 N28 1.288(8) . ? C29 N30 1.368(8) . ? C31 N27 1.312(8) . ? C31 N30 1.327(8) . ? N27 N28 1.344(7) . ? 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 O104 Cl1 O101 110.0(4) . . ? O104 Cl1 O103 111.0(4) . . ? O101 Cl1 O103 109.4(3) . . ? O104 Cl1 O102 108.5(5) . . ? O101 Cl1 O102 109.7(4) . . ? O103 Cl1 O102 108.2(4) . . ? O1 C2 C3 107.2(5) . . ? O4 C3 C2 108.5(5) . . ? O4 C5 C6 108.8(5) . . ? O7 C6 C5 108.8(5) . . ? C9 C8 O7 124.5(5) . . ? C9 C8 C13 120.1(5) . . ? O7 C8 C13 115.3(5) . . ? C8 C9 C10 119.2(6) . . ? C11 C10 C9 120.3(6) . . ? C10 C11 C12 120.6(6) . . ? C13 C12 C11 119.3(5) . . ? O14 C13 C12 125.0(5) . . ? O14 C13 C8 114.6(5) . . ? C12 C13 C8 120.4(5) . . ? O14 C15 C16 108.3(5) . . ? O17 C16 C15 109.0(4) . . ? O17 C18 C19 108.2(4) . . ? O20 C19 C18 106.6(5) . . ? O20 C21 C22 125.0(5) . . ? O20 C21 C26 114.8(5) . . ? C22 C21 C26 120.1(5) . . ? C21 C22 C23 119.9(6) . . ? C24 C23 C22 119.7(6) . . ? C23 C24 C25 121.6(6) . . ? C24 C25 C26 118.8(6) . . ? O1 C26 C25 124.8(5) . . ? O1 C26 C21 115.4(4) . . ? C25 C26 C21 119.8(5) . . ? N28 C29 N30 110.6(5) . . ? N27 C31 N30 106.5(5) . . ? C26 O1 C2 116.7(4) . . ? C5 O4 C3 111.8(4) . . ? C8 O7 C6 116.0(4) . . ? C13 O14 C15 116.0(4) . . ? C16 O17 C18 112.7(4) . . ? C21 O20 C19 117.4(4) . . ? C31 N27 N28 111.6(5) . . ? C29 N28 N27 104.9(5) . . ? C31 N30 C29 106.4(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 O1 C2 C3 O4 -61.8(6) . . . . ? O4 C5 C6 O7 67.6(6) . . . . ? O7 C8 C9 C10 178.8(5) . . . . ? C13 C8 C9 C10 -1.8(8) . . . . ? C8 C9 C10 C11 1.7(8) . . . . ? C9 C10 C11 C12 -0.6(8) . . . . ? C10 C11 C12 C13 -0.6(8) . . . . ? C11 C12 C13 O14 -179.2(5) . . . . ? C11 C12 C13 C8 0.5(8) . . . . ? C9 C8 C13 O14 -179.5(5) . . . . ? O7 C8 C13 O14 -0.1(6) . . . . ? C9 C8 C13 C12 0.7(8) . . . . ? O7 C8 C13 C12 -179.9(4) . . . . ? O14 C15 C16 O17 -63.5(6) . . . . ? O17 C18 C19 O20 61.3(6) . . . . ? O20 C21 C22 C23 -178.7(5) . . . . ? C26 C21 C22 C23 2.5(8) . . . . ? C21 C22 C23 C24 -2.0(8) . . . . ? C22 C23 C24 C25 1.4(9) . . . . ? C23 C24 C25 C26 -1.3(8) . . . . ? C24 C25 C26 O1 -179.5(5) . . . . ? C24 C25 C26 C21 1.7(8) . . . . ? O20 C21 C26 O1 -0.2(7) . . . . ? C22 C21 C26 O1 178.8(5) . . . . ? O20 C21 C26 C25 178.7(5) . . . . ? C22 C21 C26 C25 -2.3(8) . . . . ? C25 C26 O1 C2 5.4(7) . . . . ? C21 C26 O1 C2 -175.7(5) . . . . ? C3 C2 O1 C26 174.7(5) . . . . ? C6 C5 O4 C3 172.0(5) . . . . ? C2 C3 O4 C5 -170.8(5) . . . . ? C9 C8 O7 C6 -6.9(8) . . . . ? C13 C8 O7 C6 173.8(4) . . . . ? C5 C6 O7 C8 -168.6(4) . . . . ? C12 C13 O14 C15 9.8(7) . . . . ? C8 C13 O14 C15 -170.0(4) . . . . ? C16 C15 O14 C13 166.7(4) . . . . ? C15 C16 O17 C18 -168.1(5) . . . . ? C19 C18 O17 C16 163.1(5) . . . . ? C22 C21 O20 C19 3.1(8) . . . . ? C26 C21 O20 C19 -178.0(5) . . . . ? C18 C19 O20 C21 178.6(5) . . . . ? N30 C31 N27 N28 -0.7(7) . . . . ? N30 C29 N28 N27 -0.4(7) . . . . ? C31 N27 N28 C29 0.7(7) . . . . ? N27 C31 N30 C29 0.4(6) . . . . ? N28 C29 N30 C31 0.0(7) . . . . ? 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 1.94 2.738(6) 149.9 . N27 H27 O20 0.88 2.61 3.112(6) 117.0 . N30 H30 O7 0.88 2.21 2.989(6) 147.2 2_564 N30 H30 O14 0.88 2.29 2.956(6) 132.6 2_564 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.354 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.080 #===END data_comp16 _audit_creation_method ? _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '213-216' _chemical_formula_moiety 'C20 H24 O6, (C3 H4 N S)+ (Cl O4)-' _chemical_formula_sum 'C23 H28 Cl N O10 S' _chemical_formula_weight 545.97 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' '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C c' 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 17.840(1) _cell_length_b 14.251(1) _cell_length_c 12.3267(6) _cell_angle_alpha 90.00 _cell_angle_beta 129.535(3) _cell_angle_gamma 90.00 _cell_volume 2417.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.8881 _exptl_absorpt_correction_T_max 0.9850 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 '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 2798 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_av_sigmaI/netI 0.0718 _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 2.96 _diffrn_reflns_theta_max 27.85 _reflns_number_total 2798 _reflns_number_gt 2221 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0292P)^2^+2.1146P] 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 0.04(10) _refine_ls_number_reflns 2798 _refine_ls_number_parameters 326 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0738 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.0976 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.005 _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 -0.50227(7) -0.02302(9) -0.45342(11) 0.0366(3) Uani 1 1 d . . . C2 C -0.5113(3) -0.7770(3) -0.2023(5) 0.0310(10) Uani 1 1 d . . . H2A H -0.4933 -0.8413 -0.1630 0.037 Uiso 1 1 calc R . . H2B H -0.5335 -0.7792 -0.2992 0.037 Uiso 1 1 calc R . . C3 C -0.5904(3) -0.7396(4) -0.2039(5) 0.0341(10) Uani 1 1 d . . . H3A H -0.6452 -0.7846 -0.2520 0.041 Uiso 1 1 calc R . . H3B H -0.5656 -0.7311 -0.1063 0.041 Uiso 1 1 calc R . . C5 C -0.7112(3) -0.6207(3) -0.3085(5) 0.0319(10) Uani 1 1 d . . . H5A H -0.6994 -0.6032 -0.2210 0.038 Uiso 1 1 calc R . . H5B H -0.7599 -0.6718 -0.3549 0.038 Uiso 1 1 calc R . . C6 C -0.7479(3) -0.5384(3) -0.4036(5) 0.0316(10) Uani 1 1 d . . . H6A H -0.7517 -0.5536 -0.4853 0.038 Uiso 1 1 calc R . . H6B H -0.8139 -0.5216 -0.4388 0.038 Uiso 1 1 calc R . . C8 C -0.6946(3) -0.3839(3) -0.4054(4) 0.0254(9) Uani 1 1 d . . . C9 C -0.7720(3) -0.3728(3) -0.5469(4) 0.0305(10) Uani 1 1 d . . . H9 H -0.8225 -0.4182 -0.5965 0.037 Uiso 1 1 calc R . . C10 C -0.7745(3) -0.2930(4) -0.6159(5) 0.0333(10) Uani 1 1 d . . . H10 H -0.8265 -0.2852 -0.7137 0.040 Uiso 1 1 calc R . . C11 C -0.7034(3) -0.2262(3) -0.5446(5) 0.0333(10) Uani 1 1 d . . . H11 H -0.7069 -0.1720 -0.5925 0.040 Uiso 1 1 calc R . . C12 C -0.6254(3) -0.2378(4) -0.4012(5) 0.0320(10) Uani 1 1 d . . . H12 H -0.5753 -0.1920 -0.3522 0.038 Uiso 1 1 calc R . . C13 C -0.6211(3) -0.3153(3) -0.3313(4) 0.0280(9) Uani 1 1 d . . . C15 C -0.4637(3) -0.2745(3) -0.1173(5) 0.0315(10) Uani 1 1 d . . . H15A H -0.4799 -0.2134 -0.0985 0.038 Uiso 1 1 calc R . . H15B H -0.4445 -0.2629 -0.1759 0.038 Uiso 1 1 calc R . . C16 C -0.3816(3) -0.3192(3) 0.0182(5) 0.0315(10) Uani 1 1 d . . . H16A H -0.3262 -0.2750 0.0737 0.038 Uiso 1 1 calc R . . H16B H -0.4022 -0.3350 0.0739 0.038 Uiso 1 1 calc R . . C18 C -0.2635(3) -0.4389(3) 0.1128(4) 0.0304(10) Uani 1 1 d . . . H18A H -0.2743 -0.4665 0.1756 0.036 Uiso 1 1 calc R . . H18B H -0.2150 -0.3880 0.1643 0.036 Uiso 1 1 calc R . . C19 C -0.2272(3) -0.5126(3) 0.0699(5) 0.0307(10) Uani 1 1 d . . . H19A H -0.2225 -0.4868 -0.0002 0.037 Uiso 1 1 calc R . . H19B H -0.1619 -0.5342 0.1526 0.037 Uiso 1 1 calc R . . C21 C -0.2821(3) -0.6596(3) -0.0525(4) 0.0288(10) Uani 1 1 d . . . C22 C -0.2048(3) -0.6656(3) -0.0533(4) 0.0296(10) Uani 1 1 d . . . H22 H -0.1559 -0.6185 -0.0088 0.036 Uiso 1 1 calc R . . C23 C -0.1993(3) -0.7416(4) -0.1200(5) 0.0358(11) Uani 1 1 d . . . H23 H -0.1463 -0.7462 -0.1203 0.043 Uiso 1 1 calc R . . C24 C -0.2699(3) -0.8092(4) -0.1847(5) 0.0364(11) Uani 1 1 d . . . H24 H -0.2652 -0.8607 -0.2289 0.044 Uiso 1 1 calc R . . C25 C -0.3481(3) -0.8032(3) -0.1863(4) 0.0314(10) Uani 1 1 d . . . H25 H -0.3973 -0.8500 -0.2327 0.038 Uiso 1 1 calc R . . C26 C -0.3543(3) -0.7289(3) -0.1200(4) 0.0241(9) Uani 1 1 d . . . C28 C -0.4655(3) -0.5544(4) 0.0360(5) 0.0369(11) Uani 1 1 d . . . H28 H -0.4481 -0.5873 -0.0120 0.044 Uiso 1 1 calc R A 1 C30 C -0.5489(3) -0.4500(4) 0.0597(4) 0.0330(10) Uani 1 1 d . . . H30 H -0.5956 -0.4020 0.0288 0.040 Uiso 1 1 calc R B 1 O1 O -0.4288(2) -0.7149(2) -0.1160(3) 0.0323(7) Uani 1 1 d . . . O4 O -0.6229(2) -0.6516(2) -0.2762(3) 0.0306(7) Uani 1 1 d . . . O7 O -0.6822(2) -0.4603(2) -0.3261(3) 0.0288(7) Uani 1 1 d . . . O14 O -0.54697(19) -0.3352(2) -0.1909(3) 0.0275(7) Uani 1 1 d . . . O17 O -0.3526(2) -0.4023(2) -0.0110(3) 0.0296(7) Uani 1 1 d . . . O20 O -0.2950(2) -0.5894(2) 0.0100(3) 0.0299(7) Uani 1 1 d . . . O101 O -0.5028(3) -0.0059(3) -0.3396(4) 0.0592(11) Uani 1 1 d . . . O102 O -0.4420(3) -0.1028(3) -0.4215(4) 0.0630(12) Uani 1 1 d . . . O103 O -0.5992(3) -0.0431(3) -0.5781(4) 0.0611(11) Uani 1 1 d . . . O104 O -0.4635(4) 0.0565(3) -0.4730(5) 0.0742(14) Uani 1 1 d . . . N29 N -0.5349(3) -0.4894(3) -0.0261(4) 0.0346(9) Uani 1 1 d . C . H29 H -0.5687 -0.4735 -0.1150 0.041 Uiso 1 1 calc R . . S27 S -0.41537(13) -0.57226(15) 0.19316(17) 0.0406(6) Uani 0.561(6) 1 d P C 1 C31 C -0.48295(14) -0.48887(16) 0.2128(2) 0.0359(7) Uani 0.561(6) 1 d P C 1 H31 H -0.4793 -0.4738 0.2912 0.043 Uiso 0.561(6) 1 calc PR C 1 S27B S -0.48295(14) -0.48887(16) 0.2128(2) 0.0359(7) Uani 0.439(6) 1 d P C 2 C31B C -0.41537(13) -0.57226(15) 0.19316(17) 0.0406(6) Uani 0.439(6) 1 d P C 2 H31B H -0.3646 -0.6142 0.2592 0.049 Uiso 0.439(6) 1 calc PR C 2 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 0.0339(6) 0.0405(7) 0.0374(6) -0.0019(5) 0.0236(5) -0.0013(5) C2 0.033(2) 0.025(3) 0.033(2) -0.0023(18) 0.021(2) -0.0051(19) C3 0.035(2) 0.036(3) 0.038(2) 0.002(2) 0.027(2) -0.004(2) C5 0.031(2) 0.032(3) 0.037(2) -0.006(2) 0.024(2) -0.007(2) C6 0.024(2) 0.029(3) 0.036(2) -0.0043(19) 0.017(2) -0.0063(19) C8 0.024(2) 0.029(3) 0.0264(19) 0.0008(17) 0.0170(17) 0.0030(18) C9 0.032(2) 0.034(3) 0.030(2) -0.0048(18) 0.0214(19) 0.0008(19) C10 0.036(2) 0.042(3) 0.027(2) 0.007(2) 0.0223(19) 0.012(2) C11 0.036(2) 0.034(3) 0.039(2) 0.007(2) 0.027(2) 0.012(2) C12 0.032(2) 0.036(3) 0.036(2) 0.001(2) 0.026(2) 0.002(2) C13 0.027(2) 0.033(3) 0.026(2) 0.0028(18) 0.0183(18) 0.0063(19) C15 0.029(2) 0.031(3) 0.037(2) -0.005(2) 0.023(2) -0.002(2) C16 0.031(2) 0.031(3) 0.030(2) -0.0086(19) 0.0183(19) -0.007(2) C18 0.026(2) 0.038(3) 0.023(2) -0.0026(19) 0.0137(19) -0.0025(19) C19 0.022(2) 0.036(3) 0.032(2) -0.007(2) 0.0164(19) -0.005(2) C21 0.033(2) 0.036(3) 0.0234(19) 0.0024(18) 0.0204(19) 0.005(2) C22 0.030(2) 0.032(3) 0.028(2) 0.0059(18) 0.0191(19) 0.0052(19) C23 0.039(3) 0.045(3) 0.032(2) 0.010(2) 0.027(2) 0.015(2) C24 0.043(3) 0.040(3) 0.030(2) 0.006(2) 0.025(2) 0.013(2) C25 0.037(2) 0.030(3) 0.026(2) 0.0055(18) 0.020(2) 0.008(2) C26 0.025(2) 0.029(2) 0.0200(18) 0.0036(17) 0.0153(17) 0.0054(18) C28 0.040(3) 0.034(3) 0.045(3) -0.004(2) 0.030(2) -0.006(2) C30 0.035(2) 0.033(3) 0.034(2) 0.000(2) 0.023(2) 0.002(2) O1 0.0307(16) 0.037(2) 0.0316(15) -0.0068(13) 0.0209(14) -0.0052(14) O4 0.0286(15) 0.0325(19) 0.0371(16) 0.0036(14) 0.0239(14) 0.0007(13) O7 0.0293(16) 0.0304(18) 0.0235(14) -0.0015(12) 0.0153(13) -0.0037(13) O14 0.0223(14) 0.0336(19) 0.0225(14) -0.0037(12) 0.0124(12) -0.0048(13) O17 0.0263(15) 0.0350(19) 0.0222(13) -0.0034(13) 0.0130(12) 0.0017(14) O20 0.0290(15) 0.0333(19) 0.0311(15) -0.0067(14) 0.0208(13) -0.0048(14) O101 0.063(2) 0.083(3) 0.050(2) -0.016(2) 0.045(2) -0.005(2) O102 0.056(2) 0.065(3) 0.058(2) 0.009(2) 0.032(2) 0.029(2) O103 0.036(2) 0.082(3) 0.040(2) -0.008(2) 0.0125(17) -0.002(2) O104 0.105(4) 0.057(3) 0.092(3) -0.016(2) 0.078(3) -0.037(3) N29 0.035(2) 0.041(2) 0.0245(18) 0.0055(17) 0.0175(17) 0.0042(19) S27 0.0402(11) 0.0506(13) 0.0342(10) 0.0066(8) 0.0252(9) 0.0042(9) C31 0.0331(12) 0.0395(14) 0.0335(11) 0.0033(9) 0.0204(9) 0.0011(9) S27B 0.0331(12) 0.0395(14) 0.0335(11) 0.0033(9) 0.0204(9) 0.0011(9) C31B 0.0402(11) 0.0506(13) 0.0342(10) 0.0066(8) 0.0252(9) 0.0042(9) _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 O104 1.426(4) . ? Cl1 O101 1.429(3) . ? Cl1 O103 1.432(4) . ? Cl1 O102 1.437(4) . ? C2 O1 1.445(5) . ? C2 C3 1.497(6) . ? C3 O4 1.430(6) . ? C5 O4 1.426(5) . ? C5 C6 1.484(7) . ? C6 O7 1.449(5) . ? C8 C9 1.381(6) . ? C8 O7 1.384(5) . ? C8 C13 1.409(6) . ? C9 C10 1.404(7) . ? C10 C11 1.367(7) . ? C11 C12 1.399(6) . ? C12 C13 1.373(6) . ? C13 O14 1.382(5) . ? C15 O14 1.437(5) . ? C15 C16 1.492(7) . ? C16 O17 1.427(5) . ? C18 O17 1.428(5) . ? C18 C19 1.496(6) . ? C19 O20 1.439(5) . ? C21 O20 1.368(5) . ? C21 C22 1.387(6) . ? C21 C26 1.401(6) . ? C22 C23 1.400(7) . ? C23 C24 1.368(7) . ? C24 C25 1.387(6) . ? C25 C26 1.384(6) . ? C26 O1 1.375(5) . ? C28 N29 1.330(6) . ? C28 S27 1.553(5) . ? C30 N29 1.354(6) . ? C30 C31 1.558(5) . ? S27 C31 1.816(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 O104 Cl1 O101 109.7(3) . . ? O104 Cl1 O103 111.2(3) . . ? O101 Cl1 O103 109.3(2) . . ? O104 Cl1 O102 108.4(3) . . ? O101 Cl1 O102 109.7(3) . . ? O103 Cl1 O102 108.5(3) . . ? O1 C2 C3 107.6(4) . . ? O4 C3 C2 108.9(3) . . ? O4 C5 C6 108.6(4) . . ? O7 C6 C5 108.8(3) . . ? C9 C8 O7 124.3(4) . . ? C9 C8 C13 120.7(4) . . ? O7 C8 C13 115.0(3) . . ? C8 C9 C10 118.5(4) . . ? C11 C10 C9 121.1(4) . . ? C10 C11 C12 120.0(4) . . ? C13 C12 C11 120.1(4) . . ? C12 C13 O14 125.3(4) . . ? C12 C13 C8 119.6(4) . . ? O14 C13 C8 115.1(4) . . ? O14 C15 C16 109.5(4) . . ? O17 C16 C15 109.1(3) . . ? O17 C18 C19 108.4(3) . . ? O20 C19 C18 107.7(3) . . ? O20 C21 C22 125.0(4) . . ? O20 C21 C26 115.4(3) . . ? C22 C21 C26 119.6(4) . . ? C21 C22 C23 119.6(4) . . ? C24 C23 C22 120.3(4) . . ? C23 C24 C25 120.7(5) . . ? C26 C25 C24 119.7(5) . . ? O1 C26 C25 125.0(4) . . ? O1 C26 C21 114.9(4) . . ? C25 C26 C21 120.1(4) . . ? N29 C28 S27 114.8(4) . . ? N29 C30 C31 115.3(4) . . ? C26 O1 C2 116.1(3) . . ? C5 O4 C3 112.5(3) . . ? C8 O7 C6 116.1(3) . . ? C13 O14 C15 116.6(3) . . ? C16 O17 C18 111.7(3) . . ? C21 O20 C19 117.3(3) . . ? C28 N29 C30 113.9(4) . . ? C28 S27 C31 98.9(2) . . ? C30 C31 S27 97.2(2) . . ? 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 66.7(4) . . . . ? O4 C5 C6 O7 -68.0(4) . . . . ? O7 C8 C9 C10 -178.3(4) . . . . ? C13 C8 C9 C10 1.6(6) . . . . ? C8 C9 C10 C11 -1.6(6) . . . . ? C9 C10 C11 C12 1.4(6) . . . . ? C10 C11 C12 C13 -1.2(6) . . . . ? C11 C12 C13 O14 178.6(4) . . . . ? C11 C12 C13 C8 1.3(6) . . . . ? C9 C8 C13 C12 -1.5(6) . . . . ? O7 C8 C13 C12 178.4(4) . . . . ? C9 C8 C13 O14 -179.1(4) . . . . ? O7 C8 C13 O14 0.8(5) . . . . ? O14 C15 C16 O17 65.2(4) . . . . ? O17 C18 C19 O20 -66.1(4) . . . . ? O20 C21 C22 C23 179.4(4) . . . . ? C26 C21 C22 C23 -0.8(6) . . . . ? C21 C22 C23 C24 0.3(7) . . . . ? C22 C23 C24 C25 0.5(7) . . . . ? C23 C24 C25 C26 -1.0(6) . . . . ? C24 C25 C26 O1 179.1(4) . . . . ? C24 C25 C26 C21 0.5(6) . . . . ? O20 C21 C26 O1 1.4(5) . . . . ? C22 C21 C26 O1 -178.4(4) . . . . ? O20 C21 C26 C25 -179.8(4) . . . . ? C22 C21 C26 C25 0.4(6) . . . . ? C25 C26 O1 C2 -7.8(6) . . . . ? C21 C26 O1 C2 170.9(3) . . . . ? C3 C2 O1 C26 -169.9(4) . . . . ? C6 C5 O4 C3 -170.5(3) . . . . ? C2 C3 O4 C5 167.6(4) . . . . ? C9 C8 O7 C6 9.3(6) . . . . ? C13 C8 O7 C6 -170.6(3) . . . . ? C5 C6 O7 C8 167.6(3) . . . . ? C12 C13 O14 C15 -6.6(6) . . . . ? C8 C13 O14 C15 170.8(3) . . . . ? C16 C15 O14 C13 -165.2(4) . . . . ? C15 C16 O17 C18 169.4(3) . . . . ? C19 C18 O17 C16 -168.1(4) . . . . ? C22 C21 O20 C19 5.1(6) . . . . ? C26 C21 O20 C19 -174.7(4) . . . . ? C18 C19 O20 C21 172.0(3) . . . . ? S27 C28 N29 C30 0.4(5) . . . . ? C31 C30 N29 C28 -1.0(6) . . . . ? N29 C28 S27 C31 0.2(4) . . . . ? N29 C30 C31 S27 1.0(4) . . . . ? C28 S27 C31 C30 -0.6(3) . . . . ? 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 O7 0.88 2.05 2.895(5) 160.9 . N29 H29 O14 0.88 2.32 2.905(5) 124.3 . _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.276 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.062 #===END data_comp8 _audit_creation_method ? _chemical_name_systematic ; ? ; _chemical_melting_point '124-126' _chemical_name_common ? _chemical_formula_moiety 'C16 H24 O6 (C3 H5 N2)+ (Cl O4)-' _chemical_formula_sum 'C19 H29 Cl N2 O10' _chemical_formula_weight 480.89 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 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7990(2) _cell_length_b 37.641(1) _cell_length_c 12.3724(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.016(1) _cell_angle_gamma 90.00 _cell_volume 4557.17(19) _cell_formula_units_Z 8 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 0.224 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.9057 _exptl_absorpt_correction_T_max 0.9779 _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 '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 9122 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 46 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 26.33 _reflns_number_total 9122 _reflns_number_gt 5546 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+2.7743P] 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 9122 _refine_ls_number_parameters 577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1274 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1666 _refine_ls_wR_factor_gt 0.1354 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C2A C 0.5830(3) -0.06348(9) 1.9498(2) 0.0320(8) Uani 1 d . . . H2A1 H 0.6382 -0.0435 1.9803 0.038 Uiso 1 calc R . . H2A2 H 0.5893 -0.0633 1.8702 0.038 Uiso 1 calc R . . C2B C 0.0167(4) -0.06834(9) 1.4789(3) 0.0416(9) Uani 1 d . . . H2B1 H -0.0726 -0.0598 1.5024 0.050 Uiso 1 calc R . . H2B2 H 0.0305 -0.0587 1.4058 0.050 Uiso 1 calc R . . C3A C 0.6365(3) -0.09781(9) 1.9952(3) 0.0356(8) Uani 1 d . . . H3A1 H 0.7343 -0.1004 1.9806 0.043 Uiso 1 calc R . . H3A2 H 0.6277 -0.0983 2.0745 0.043 Uiso 1 calc R . . C3B C 0.1280(4) -0.05598(10) 1.5559(3) 0.0466(9) Uani 1 d . . . H3B1 H 0.1266 -0.0297 1.5596 0.056 Uiso 1 calc R . . H3B2 H 0.1123 -0.0653 1.6290 0.056 Uiso 1 calc R . . C5A C 0.6246(3) -0.15973(9) 1.9593(3) 0.0437(9) Uani 1 d . . . H5A1 H 0.6399 -0.1653 2.0372 0.052 Uiso 1 calc R . . H5A2 H 0.7141 -0.1596 1.9257 0.052 Uiso 1 calc R . . C5B C 0.3684(4) -0.04567(10) 1.5693(3) 0.0580(12) Uani 1 d . . . H5B1 H 0.3498 -0.0394 1.6448 0.070 Uiso 1 calc R . . H5B2 H 0.3734 -0.0234 1.5273 0.070 Uiso 1 calc R . . C6A C 0.5327(3) -0.18692(10) 1.9057(3) 0.0435(9) Uani 1 d . . . H6A1 H 0.5002 -0.1785 1.8330 0.052 Uiso 1 calc R . . H6A2 H 0.5831 -0.2095 1.8971 0.052 Uiso 1 calc R . . C6B C 0.5005(4) -0.06474(11) 1.5673(3) 0.0531(11) Uani 1 d . . . H6B1 H 0.5074 -0.0769 1.4967 0.064 Uiso 1 calc R . . H6B2 H 0.5769 -0.0476 1.5763 0.064 Uiso 1 calc R . . C8A C 0.3082(3) -0.20879(9) 1.9140(3) 0.0350(8) Uani 1 d . . . H8A1 H 0.3379 -0.2316 1.8830 0.042 Uiso 1 calc R . . H8A2 H 0.2753 -0.1932 1.8536 0.042 Uiso 1 calc R . . C8B C 0.6340(4) -0.11002(11) 1.6657(3) 0.0544(11) Uani 1 d . . . H8B1 H 0.6453 -0.1180 1.7419 0.065 Uiso 1 calc R . . H8B2 H 0.7122 -0.0944 1.6511 0.065 Uiso 1 calc R . . C9A C 0.1953(3) -0.21533(9) 1.9877(2) 0.0341(8) Uani 1 d . . . H9A1 H 0.1168 -0.2265 1.9471 0.041 Uiso 1 calc R . . H9A2 H 0.2267 -0.2316 2.0467 0.041 Uiso 1 calc R . . C9B C 0.6361(4) -0.14102(11) 1.5943(3) 0.0541(10) Uani 1 d . . . H9B1 H 0.6340 -0.1333 1.5178 0.065 Uiso 1 calc R . . H9B2 H 0.7207 -0.1549 1.6097 0.065 Uiso 1 calc R . . C11A C 0.0283(3) -0.18375(9) 2.0809(3) 0.0340(8) Uani 1 d . . . H11A H 0.0307 -0.2023 2.1377 0.041 Uiso 1 calc R . . H11B H -0.0455 -0.1897 2.0262 0.041 Uiso 1 calc R . . C11B C 0.5257(4) -0.19527(10) 1.5577(3) 0.0417(9) Uani 1 d . . . H11C H 0.6087 -0.2084 1.5834 0.050 Uiso 1 calc R . . H11D H 0.5309 -0.1911 1.4790 0.050 Uiso 1 calc R . . C12A C 0.0022(3) -0.14817(9) 2.1295(2) 0.0327(8) Uani 1 d . . . H12A H -0.0892 -0.1479 2.1601 0.039 Uiso 1 calc R . . H12B H 0.0715 -0.1432 2.1887 0.039 Uiso 1 calc R . . C12B C 0.4025(3) -0.21648(9) 1.5781(3) 0.0399(9) Uani 1 d . . . H12C H 0.4177 -0.2415 1.5576 0.048 Uiso 1 calc R . . H12D H 0.3855 -0.2158 1.6563 0.048 Uiso 1 calc R . . C14A C 0.0003(3) -0.08663(9) 2.0898(2) 0.0319(8) Uani 1 d . . . H14A H 0.0657 -0.0841 2.1531 0.038 Uiso 1 calc R . . H14B H -0.0928 -0.0824 2.1143 0.038 Uiso 1 calc R . . C14B C 0.1665(3) -0.22179(9) 1.5425(3) 0.0375(8) Uani 1 d . . . H14C H 0.1423 -0.2161 1.6172 0.045 Uiso 1 calc R . . H14D H 0.1837 -0.2477 1.5383 0.045 Uiso 1 calc R . . C15A C 0.0326(3) -0.05997(9) 2.0050(2) 0.0320(8) Uani 1 d . . . H15A H -0.0189 -0.0656 1.9362 0.038 Uiso 1 calc R . . H15B H 0.0061 -0.0359 2.0282 0.038 Uiso 1 calc R . . C15B C 0.0504(3) -0.21189(9) 1.4645(3) 0.0349(8) Uani 1 d . . . H15C H 0.0720 -0.2186 1.3899 0.042 Uiso 1 calc R . . H15D H -0.0337 -0.2246 1.4831 0.042 Uiso 1 calc R . . C17A C 0.2259(3) -0.03556(8) 1.9238(2) 0.0295(7) Uani 1 d . . . C17B C -0.0786(3) -0.16003(9) 1.4132(2) 0.0312(8) Uani 1 d . . . C18A C 0.1461(3) -0.01246(9) 1.8618(3) 0.0354(8) Uani 1 d . . . H18A H 0.0493 -0.0140 1.8623 0.042 Uiso 1 calc R . . C18B C -0.1796(3) -0.17906(10) 1.3568(2) 0.0390(8) Uani 1 d . . . H18B H -0.1752 -0.2043 1.3549 0.047 Uiso 1 calc R . . C19A C 0.2064(4) 0.01318(9) 1.7982(3) 0.0389(8) Uani 1 d . . . H19A H 0.1505 0.0291 1.7558 0.047 Uiso 1 calc R . . C19B C -0.2880(3) -0.16140(12) 1.3025(3) 0.0431(10) Uani 1 d . . . H19B H -0.3577 -0.1746 1.2643 0.052 Uiso 1 calc R . . C20A C 0.3456(4) 0.01549(9) 1.7967(3) 0.0397(9) Uani 1 d . . . H20A H 0.3862 0.0334 1.7547 0.048 Uiso 1 calc R . . C20B C -0.2941(3) -0.12534(12) 1.3041(3) 0.0447(10) Uani 1 d . . . H20B H -0.3679 -0.1135 1.2666 0.054 Uiso 1 calc R . . C21A C 0.4279(3) -0.00823(9) 1.8564(2) 0.0338(8) Uani 1 d . . . H21A H 0.5245 -0.0068 1.8542 0.041 Uiso 1 calc R . . C21B C -0.1931(3) -0.10557(10) 1.3602(3) 0.0394(9) Uani 1 d . . . H21B H -0.1977 -0.0804 1.3606 0.047 Uiso 1 calc R . . C22A C 0.3694(3) -0.03402(8) 1.9191(2) 0.0282(7) Uani 1 d . . . C22B C -0.0853(3) -0.12302(9) 1.4159(2) 0.0326(8) Uani 1 d . . . C24A C 0.2640(3) -0.11745(8) 1.8315(2) 0.0287(7) Uani 1 d . . . H24A H 0.3277 -0.1061 1.8808 0.034 Uiso 1 calc R . . C26B C 0.3580(3) -0.13577(13) 1.1821(3) 0.0522(11) Uani 1 d . . . H26B H 0.3805 -0.1427 1.1115 0.063 Uiso 1 calc R . . C26A C 0.0823(3) -0.14438(9) 1.7632(3) 0.0374(8) Uani 1 d . . . H26A H -0.0050 -0.1554 1.7575 0.045 Uiso 1 calc R . . C24B C 0.3082(4) -0.13808(14) 1.3507(3) 0.0544(11) Uani 1 d . . . H24B H 0.2895 -0.1467 1.4206 0.065 Uiso 1 calc R . . C27A C 0.1673(4) -0.14024(9) 1.6837(3) 0.0392(9) Uani 1 d . . . H27A H 0.1523 -0.1475 1.6105 0.047 Uiso 1 calc R . . N27B N 0.3092(3) -0.10533(9) 1.3218(3) 0.0478(8) Uani 1 d . . . H27B H 0.2920 -0.0872 1.3638 0.057 Uiso 1 calc R . . O102 O 0.8773(3) 0.02998(8) 1.7446(2) 0.0662(8) Uani 1 d . . . O1A O 0.4429(2) -0.05947(6) 1.97679(15) 0.0299(5) Uani 1 d . . . O1B O 0.0175(2) -0.10642(6) 1.47578(17) 0.0356(5) Uani 1 d . . . O101 O 0.8267(3) -0.01284(8) 1.6157(2) 0.0753(9) Uani 1 d . . . O4A O 0.5600(2) -0.12609(6) 1.94589(17) 0.0360(5) Uani 1 d . . . O4B O 0.2588(2) -0.06749(6) 1.52373(17) 0.0416(6) Uani 1 d . . . O7A O 0.4192(2) -0.19255(6) 1.97135(17) 0.0405(6) Uani 1 d . . . O7B O 0.5090(2) -0.08990(6) 1.65161(19) 0.0464(6) Uani 1 d . . . O10A O 0.1552(2) -0.18232(6) 2.03182(16) 0.0325(5) Uani 1 d . . . O10B O 0.5197(2) -0.16237(6) 1.61253(18) 0.0428(6) Uani 1 d . . . O103 O 0.6512(2) 0.01886(8) 1.6903(2) 0.0652(8) Uani 1 d . . . O104 O 0.7767(3) -0.02271(9) 1.7956(3) 0.0849(11) Uani 1 d . . . O13A O 0.0088(2) -0.12159(6) 2.04699(15) 0.0308(5) Uani 1 d . . . O13B O 0.2863(2) -0.20290(6) 1.51758(16) 0.0341(5) Uani 1 d . . . O16A O 0.1770(2) -0.06123(5) 1.99014(15) 0.0299(5) Uani 1 d . . . O16B O 0.0303(2) -0.17442(6) 1.47143(16) 0.0333(5) Uani 1 d . . . N27A N 0.2802(3) -0.12347(7) 1.7279(2) 0.0338(7) Uani 1 d . . . H27A H 0.3527 -0.1176 1.6929 0.041 Uiso 1 calc R . . C27B C 0.3406(3) -0.10300(11) 1.2173(3) 0.0478(10) Uani 1 d . . . H27B H 0.3487 -0.0818 1.1765 0.057 Uiso 1 calc R . . N29A N 0.1437(3) -0.12992(7) 1.85422(19) 0.0293(6) Uani 1 d . . . H29A H 0.1083 -0.1291 1.9181 0.035 Uiso 1 calc R . . N29B N 0.3372(3) -0.15757(9) 1.2678(3) 0.0585(10) Uani 1 d . . . H29B H 0.3425 -0.1809 1.2673 0.070 Uiso 1 calc R . . Cl1A Cl 0.78336(8) 0.00278(2) 1.71229(7) 0.0401(2) Uani 1 d . . . Cl2B Cl 0.36082(9) -0.25920(3) 1.26752(6) 0.0447(3) Uani 1 d . . . O105 O 0.3693(3) -0.28177(7) 1.1759(2) 0.0582(7) Uani 1 d . . . O107 O 0.3555(3) -0.27949(8) 1.3636(2) 0.0628(8) Uani 1 d . . . O106 O 0.2409(4) -0.23798(11) 1.2545(2) 0.1061(15) Uani 1 d . . . O108 O 0.4777(4) -0.23653(10) 1.2764(3) 0.1037(13) Uani 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 C2A 0.0287(17) 0.034(2) 0.0336(17) -0.0059(15) 0.0061(14) -0.0055(15) C2B 0.050(2) 0.030(2) 0.046(2) 0.0039(16) 0.0111(17) 0.0032(17) C3A 0.0287(17) 0.043(2) 0.0349(18) 0.0002(16) -0.0040(14) -0.0033(16) C3B 0.072(3) 0.027(2) 0.041(2) -0.0073(16) 0.0090(19) 0.0007(19) C5A 0.0349(19) 0.040(2) 0.057(2) 0.0112(18) 0.0040(17) 0.0133(17) C5B 0.091(3) 0.033(2) 0.047(2) 0.0027(18) -0.024(2) -0.023(2) C6A 0.043(2) 0.034(2) 0.055(2) 0.0034(17) 0.0114(18) 0.0080(17) C6B 0.053(2) 0.064(3) 0.041(2) 0.000(2) -0.0036(18) -0.027(2) C8A 0.044(2) 0.0238(19) 0.0370(18) -0.0004(14) -0.0022(16) 0.0062(16) C8B 0.040(2) 0.062(3) 0.062(3) -0.009(2) 0.0103(19) -0.007(2) C9A 0.043(2) 0.0268(19) 0.0322(17) 0.0033(14) -0.0029(15) -0.0003(16) C9B 0.041(2) 0.057(3) 0.066(3) 0.000(2) 0.0094(19) -0.005(2) C11A 0.0358(19) 0.033(2) 0.0336(18) 0.0035(15) 0.0023(15) -0.0074(16) C11B 0.041(2) 0.045(2) 0.0391(19) -0.0078(17) 0.0027(16) 0.0107(18) C12A 0.0327(18) 0.038(2) 0.0274(16) 0.0036(15) 0.0050(14) -0.0055(15) C12B 0.044(2) 0.034(2) 0.0416(19) -0.0039(16) -0.0050(16) 0.0098(17) C14A 0.0284(17) 0.034(2) 0.0340(17) -0.0098(15) 0.0072(14) -0.0015(15) C14B 0.042(2) 0.026(2) 0.044(2) 0.0001(15) -0.0004(16) -0.0003(16) C15A 0.0285(17) 0.0284(19) 0.0399(18) -0.0037(15) 0.0093(14) 0.0032(15) C15B 0.0376(19) 0.028(2) 0.0392(19) -0.0076(15) 0.0010(15) -0.0045(16) C17A 0.0367(19) 0.0235(18) 0.0289(16) -0.0040(14) 0.0083(14) 0.0001(15) C17B 0.0290(17) 0.037(2) 0.0279(17) 0.0020(14) 0.0057(14) 0.0013(16) C18A 0.0386(19) 0.030(2) 0.0382(19) -0.0038(15) 0.0054(15) 0.0017(16) C18B 0.0370(19) 0.048(2) 0.0321(18) 0.0003(16) 0.0031(15) -0.0076(18) C19A 0.051(2) 0.028(2) 0.0379(19) 0.0003(15) 0.0077(16) 0.0063(17) C19B 0.0279(18) 0.073(3) 0.0279(18) 0.0047(18) 0.0016(14) -0.0073(19) C20A 0.057(2) 0.024(2) 0.0387(19) 0.0006(15) 0.0114(17) -0.0016(17) C20B 0.0302(19) 0.071(3) 0.0331(19) 0.0135(19) 0.0027(15) 0.005(2) C21A 0.0417(19) 0.0275(19) 0.0326(18) -0.0053(14) 0.0059(15) -0.0073(16) C21B 0.038(2) 0.045(2) 0.0361(18) 0.0149(16) 0.0123(16) 0.0091(18) C22A 0.0349(18) 0.0237(18) 0.0262(16) -0.0031(13) 0.0041(13) -0.0013(15) C22B 0.0305(18) 0.040(2) 0.0275(17) 0.0050(15) 0.0067(14) 0.0024(16) C24A 0.0307(18) 0.0263(19) 0.0288(17) -0.0036(13) -0.0001(14) 0.0025(15) C26B 0.030(2) 0.087(4) 0.040(2) -0.019(2) 0.0026(16) 0.001(2) C26A 0.0346(19) 0.034(2) 0.043(2) -0.0001(16) -0.0059(16) -0.0052(16) C24B 0.040(2) 0.080(4) 0.043(2) 0.019(2) -0.0023(18) 0.000(2) C27A 0.054(2) 0.038(2) 0.0250(17) -0.0034(15) -0.0015(16) 0.0005(18) N27B 0.0373(17) 0.053(2) 0.053(2) -0.0206(17) -0.0018(15) 0.0042(16) O102 0.0723(19) 0.060(2) 0.0655(18) -0.0059(15) -0.0074(15) -0.0285(16) O1A 0.0277(11) 0.0320(13) 0.0302(11) -0.0006(10) 0.0053(9) -0.0031(10) O1B 0.0395(13) 0.0271(14) 0.0401(13) 0.0002(10) 0.0008(10) 0.0032(11) O101 0.087(2) 0.069(2) 0.071(2) -0.0275(16) 0.0162(17) 0.0126(18) O4A 0.0306(12) 0.0315(14) 0.0450(13) 0.0018(10) -0.0054(10) 0.0014(11) O4B 0.0517(15) 0.0351(15) 0.0379(13) -0.0083(11) 0.0024(11) -0.0125(12) O7A 0.0419(14) 0.0443(16) 0.0356(13) 0.0022(11) 0.0047(11) -0.0059(12) O7B 0.0466(15) 0.0383(16) 0.0555(15) -0.0007(12) 0.0154(12) -0.0050(12) O10A 0.0380(13) 0.0266(13) 0.0337(12) -0.0021(10) 0.0083(10) -0.0040(10) O10B 0.0352(13) 0.0410(16) 0.0531(15) -0.0076(12) 0.0119(11) -0.0041(12) O103 0.0395(15) 0.084(2) 0.0724(18) 0.0188(16) 0.0100(13) 0.0148(15) O104 0.0605(19) 0.090(3) 0.105(2) 0.062(2) 0.0174(17) -0.0024(17) O13A 0.0396(13) 0.0268(13) 0.0266(11) -0.0018(9) 0.0079(9) -0.0031(10) O13B 0.0335(13) 0.0327(14) 0.0361(12) 0.0016(10) 0.0015(10) 0.0054(11) O16A 0.0303(12) 0.0265(13) 0.0336(12) 0.0019(10) 0.0088(9) -0.0017(10) O16B 0.0335(12) 0.0276(13) 0.0379(12) -0.0014(10) -0.0057(10) 0.0005(10) N27A 0.0369(16) 0.0349(17) 0.0307(15) 0.0010(12) 0.0124(12) -0.0027(13) C27B 0.0299(19) 0.051(3) 0.061(3) 0.022(2) -0.0073(18) -0.0057(18) N29A 0.0334(15) 0.0306(16) 0.0247(13) 0.0014(11) 0.0079(11) 0.0000(12) N29B 0.0397(19) 0.031(2) 0.103(3) -0.006(2) -0.0108(19) 0.0035(15) Cl1A 0.0372(5) 0.0398(5) 0.0439(5) 0.0010(4) 0.0076(4) -0.0079(4) Cl2B 0.0577(6) 0.0428(6) 0.0333(5) 0.0027(4) 0.0004(4) 0.0086(5) O105 0.0613(17) 0.0571(19) 0.0560(16) -0.0223(14) 0.0012(13) 0.0121(14) O107 0.0614(17) 0.073(2) 0.0530(16) 0.0304(15) -0.0048(13) -0.0046(15) O106 0.134(3) 0.141(3) 0.0431(16) 0.0055(19) 0.0071(18) 0.107(3) O108 0.137(3) 0.088(3) 0.086(2) -0.001(2) 0.010(2) -0.076(2) _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 C2A O1A 1.438(3) . ? C2A C3A 1.493(4) . ? C2B O1B 1.434(4) . ? C2B C3B 1.485(5) . ? C3A O4A 1.420(4) . ? C3B O4B 1.429(4) . ? C5A O4A 1.421(4) . ? C5A C6A 1.495(5) . ? C5B O4B 1.442(4) . ? C5B C6B 1.482(6) . ? C6A O7A 1.427(4) . ? C6B O7B 1.409(4) . ? C8A O7A 1.407(4) . ? C8A C9A 1.491(4) . ? C8B O7B 1.443(4) . ? C8B C9B 1.465(5) . ? C9A O10A 1.421(4) . ? C9B O10B 1.423(4) . ? C11A O10A 1.413(4) . ? C11A C12A 1.496(4) . ? C11B O10B 1.415(4) . ? C11B C12B 1.481(5) . ? C12A O13A 1.433(4) . ? C12B O13B 1.424(4) . ? C14A O13A 1.423(4) . ? C14A C15A 1.498(4) . ? C14B O13B 1.420(4) . ? C14B C15B 1.500(4) . ? C15A O16A 1.437(3) . ? C15B O16B 1.427(4) . ? C17A O16A 1.370(4) . ? C17A C18A 1.376(4) . ? C17A C22A 1.411(4) . ? C17B O16B 1.368(4) . ? C17B C18B 1.381(4) . ? C17B C22B 1.395(5) . ? C18A C19A 1.396(5) . ? C18B C19B 1.395(5) . ? C19A C20A 1.369(5) . ? C19B C20B 1.359(5) . ? C20A C21A 1.388(5) . ? C20B C21B 1.394(5) . ? C21A C22A 1.386(4) . ? C21B C22B 1.395(4) . ? C22A O1A 1.375(4) . ? C22B O1B 1.369(4) . ? C24A N29A 1.313(4) . ? C24A N27A 1.319(4) . ? C26B C27B 1.322(5) . ? C26B N29B 1.365(5) . ? C26A C27A 1.331(5) . ? C26A N29A 1.362(4) . ? C24B N27B 1.283(5) . ? C24B N29B 1.304(5) . ? C27A N27A 1.364(4) . ? N27B C27B 1.348(5) . ? O102 Cl1A 1.420(3) . ? O101 Cl1A 1.417(3) . ? O103 Cl1A 1.443(3) . ? O104 Cl1A 1.412(3) . ? Cl2B O107 1.416(2) . ? Cl2B O105 1.423(2) . ? Cl2B O106 1.423(3) . ? Cl2B O108 1.428(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 O1A C2A C3A 108.9(2) . . ? O1B C2B C3B 109.0(3) . . ? O4A C3A C2A 108.7(2) . . ? O4B C3B C2B 111.5(3) . . ? O4A C5A C6A 107.7(3) . . ? O4B C5B C6B 110.5(3) . . ? O7A C6A C5A 108.6(3) . . ? O7B C6B C5B 109.3(3) . . ? O7A C8A C9A 110.0(3) . . ? O7B C8B C9B 112.6(3) . . ? O10A C9A C8A 108.7(3) . . ? O10B C9B C8B 108.5(3) . . ? O10A C11A C12A 108.2(2) . . ? O10B C11B C12B 109.6(3) . . ? O13A C12A C11A 108.9(2) . . ? O13B C12B C11B 110.7(3) . . ? O13A C14A C15A 109.9(2) . . ? O13B C14B C15B 110.1(3) . . ? O16A C15A C14A 108.3(2) . . ? O16B C15B C14B 108.0(3) . . ? O16A C17A C18A 124.9(3) . . ? O16A C17A C22A 115.8(3) . . ? C18A C17A C22A 119.3(3) . . ? O16B C17B C18B 125.4(3) . . ? O16B C17B C22B 114.8(3) . . ? C18B C17B C22B 119.8(3) . . ? C17A C18A C19A 120.4(3) . . ? C17B C18B C19B 120.2(4) . . ? C20A C19A C18A 120.2(3) . . ? C20B C19B C18B 120.1(3) . . ? C19A C20A C21A 120.2(3) . . ? C19B C20B C21B 120.7(3) . . ? C22A C21A C20A 120.2(3) . . ? C20B C21B C22B 119.6(4) . . ? O1A C22A C21A 123.9(3) . . ? O1A C22A C17A 116.5(3) . . ? C21A C22A C17A 119.6(3) . . ? O1B C22B C21B 124.7(3) . . ? O1B C22B C17B 115.7(3) . . ? C21B C22B C17B 119.6(3) . . ? N29A C24A N27A 107.6(3) . . ? C27B C26B N29B 106.2(3) . . ? C27A C26A N29A 107.3(3) . . ? N27B C24B N29B 108.5(3) . . ? C26A C27A N27A 106.5(3) . . ? C24B N27B C27B 109.6(3) . . ? C22A O1A C2A 115.7(2) . . ? C22B O1B C2B 117.7(3) . . ? C3A O4A C5A 113.3(2) . . ? C3B O4B C5B 112.2(3) . . ? C8A O7A C6A 112.5(2) . . ? C6B O7B C8B 117.4(3) . . ? C11A O10A C9A 113.5(2) . . ? C11B O10B C9B 111.4(3) . . ? C14A O13A C12A 112.0(2) . . ? C14B O13B C12B 110.7(2) . . ? C17A O16A C15A 115.6(2) . . ? C17B O16B C15B 117.8(2) . . ? C24A N27A C27A 109.4(3) . . ? C26B C27B N27B 107.1(3) . . ? C24A N29A C26A 109.2(3) . . ? C24B N29B C26B 108.7(3) . . ? O104 Cl1A O101 111.2(2) . . ? O104 Cl1A O102 109.80(19) . . ? O101 Cl1A O102 108.52(18) . . ? O104 Cl1A O103 110.32(17) . . ? O101 Cl1A O103 108.74(18) . . ? O102 Cl1A O103 108.21(19) . . ? O107 Cl2B O105 110.67(18) . . ? O107 Cl2B O106 109.33(19) . . ? O105 Cl2B O106 109.09(18) . . ? O107 Cl2B O108 108.83(19) . . ? O105 Cl2B O108 109.76(19) . . ? O106 Cl2B O108 109.1(3) . . ? 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 O1A C2A C3A O4A 62.5(3) . . . . ? O1B C2B C3B O4B 60.3(4) . . . . ? O4A C5A C6A O7A -73.7(3) . . . . ? O4B C5B C6B O7B -77.2(4) . . . . ? O7A C8A C9A O10A 58.8(3) . . . . ? O7B C8B C9B O10B -56.1(4) . . . . ? O10A C11A C12A O13A 55.7(3) . . . . ? O10B C11B C12B O13B 74.7(3) . . . . ? O13A C14A C15A O16A -72.9(3) . . . . ? O13B C14B C15B O16B -58.2(3) . . . . ? O16A C17A C18A C19A 178.9(3) . . . . ? C22A C17A C18A C19A -2.6(5) . . . . ? O16B C17B C18B C19B 178.3(3) . . . . ? C22B C17B C18B C19B 0.0(4) . . . . ? C17A C18A C19A C20A 0.2(5) . . . . ? C17B C18B C19B C20B 0.6(5) . . . . ? C18A C19A C20A C21A 1.6(5) . . . . ? C18B C19B C20B C21B -0.4(5) . . . . ? C19A C20A C21A C22A -1.0(5) . . . . ? C19B C20B C21B C22B -0.4(5) . . . . ? C20A C21A C22A O1A 177.1(3) . . . . ? C20A C21A C22A C17A -1.4(4) . . . . ? O16A C17A C22A O1A 3.3(4) . . . . ? C18A C17A C22A O1A -175.4(3) . . . . ? O16A C17A C22A C21A -178.2(3) . . . . ? C18A C17A C22A C21A 3.1(4) . . . . ? C20B C21B C22B O1B -178.3(3) . . . . ? C20B C21B C22B C17B 1.1(4) . . . . ? O16B C17B C22B O1B 0.1(4) . . . . ? C18B C17B C22B O1B 178.6(3) . . . . ? O16B C17B C22B C21B -179.3(3) . . . . ? C18B C17B C22B C21B -0.9(4) . . . . ? N29A C26A C27A N27A 0.4(4) . . . . ? N29B C24B N27B C27B -0.4(4) . . . . ? C21A C22A O1A C2A -13.9(4) . . . . ? C17A C22A O1A C2A 164.5(2) . . . . ? C3A C2A O1A C22A -164.5(2) . . . . ? C21B C22B O1B C2B -2.0(4) . . . . ? C17B C22B O1B C2B 178.6(3) . . . . ? C3B C2B O1B C22B 174.7(3) . . . . ? C2A C3A O4A C5A 163.3(3) . . . . ? C6A C5A O4A C3A 179.0(3) . . . . ? C2B C3B O4B C5B 157.7(3) . . . . ? C6B C5B O4B C3B 160.3(3) . . . . ? C9A C8A O7A C6A 177.7(3) . . . . ? C5A C6A O7A C8A 161.6(3) . . . . ? C5B C6B O7B C8B -177.2(3) . . . . ? C9B C8B O7B C6B -84.0(4) . . . . ? C12A C11A O10A C9A 176.7(2) . . . . ? C8A C9A O10A C11A 165.1(2) . . . . ? C12B C11B O10B C9B -179.6(3) . . . . ? C8B C9B O10B C11B -171.5(3) . . . . ? C15A C14A O13A C12A 169.9(2) . . . . ? C11A C12A O13A C14A -173.3(2) . . . . ? C15B C14B O13B C12B -169.7(3) . . . . ? C11B C12B O13B C14B -176.2(3) . . . . ? C18A C17A O16A C15A -8.7(4) . . . . ? C22A C17A O16A C15A 172.7(2) . . . . ? C14A C15A O16A C17A -172.9(2) . . . . ? C18B C17B O16B C15B 7.1(4) . . . . ? C22B C17B O16B C15B -174.5(3) . . . . ? C14B C15B O16B C17B -174.7(2) . . . . ? N29A C24A N27A C27A -0.1(4) . . . . ? C26A C27A N27A C24A -0.3(4) . . . . ? N29B C26B C27B N27B -0.4(4) . . . . ? C24B N27B C27B C26B 0.5(4) . . . . ? N27A C24A N29A C26A 0.3(4) . . . . ? C27A C26A N29A C24A -0.5(4) . . . . ? N27B C24B N29B C26B 0.2(4) . . . . ? C27B C26B N29B C24B 0.1(4) . . . . ? 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 N27B H27B O4B 0.88 2.15 2.940(4) 148.5 . N27A H27A O7B 0.88 1.94 2.782(3) 158.9 . N27A H27A O10B 0.88 2.58 3.169(3) 124.7 . N29A H29A O13A 0.88 1.93 2.804(3) 170.3 . N29A H29A O10A 0.88 2.48 2.951(3) 114.2 . _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 26.33 _diffrn_measured_fraction_theta_full 0.968 _refine_diff_density_max 0.576 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.073 #===END data_comp9 _audit_creation_method ? _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point '155-162' _chemical_formula_moiety 'C12 H24 O6 2(C3 H5 N2)+ 2(Cl O4)-' _chemical_formula_sum 'C18 H34 Cl2 N4 O14' _chemical_formula_weight 601.39 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 'P 21/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 15.8297(3) _cell_length_b 10.8577(3) _cell_length_c 16.0071(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.859(2) _cell_angle_gamma 90.00 _cell_volume 2744.97(13) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'block' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.309 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.9131 _exptl_absorpt_correction_T_max 0.9409 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 '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 6436 _diffrn_reflns_av_R_equivalents 0.028 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 27.86 _reflns_number_total 6436 _reflns_number_gt 3836 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0352P)^2^+2.1639P] 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 6436 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1245 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1299 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.001 _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 C2A C 0.20087(17) 1.6732(3) 0.07934(18) 0.0425(7) Uani 1 1 d . . . H2A1 H 0.2258 1.7565 0.0865 0.051 Uiso 1 1 calc R . . H2A2 H 0.2477 1.6128 0.0858 0.051 Uiso 1 1 calc R . . C2B C 0.55350(19) 1.2453(3) -0.1492(2) 0.0525(9) Uani 1 1 d . . . H2B1 H 0.6027 1.2884 -0.1708 0.063 Uiso 1 1 calc R . . H2B2 H 0.5363 1.1780 -0.1885 0.063 Uiso 1 1 calc R . . C3A C 0.14153(18) 1.6518(3) 0.14684(19) 0.0429(7) Uani 1 1 d . . . H3A1 H 0.1716 1.6647 0.2024 0.051 Uiso 1 1 calc R . . H3A2 H 0.0939 1.7109 0.1408 0.051 Uiso 1 1 calc R . . C3B C 0.5764(2) 1.1942(3) -0.0642(2) 0.0540(9) Uani 1 1 d . . . H3B1 H 0.5276 1.1492 -0.0434 0.065 Uiso 1 1 calc R . . H3B2 H 0.6244 1.1360 -0.0666 0.065 Uiso 1 1 calc R . . C5A C 0.05518(18) 1.5014(3) 0.20585(16) 0.0399(7) Uani 1 1 d . . . H5A1 H 0.0067 1.5592 0.2025 0.048 Uiso 1 1 calc R . . H5A2 H 0.0864 1.5123 0.2611 0.048 Uiso 1 1 calc R . . C5B C 0.6226(2) 1.2524(3) 0.0732(2) 0.0614(10) Uani 1 1 d . . . H5B1 H 0.6669 1.1882 0.0715 0.074 Uiso 1 1 calc R . . H5B2 H 0.5727 1.2153 0.0976 0.074 Uiso 1 1 calc R . . C6A C 0.02367(17) 1.3730(3) 0.19770(17) 0.0395(7) Uani 1 1 d . . . H6A1 H 0.0720 1.3150 0.2008 0.047 Uiso 1 1 calc R . . H6A2 H -0.0126 1.3539 0.2441 0.047 Uiso 1 1 calc R . . C6B C 0.6549(2) 1.3557(4) 0.1268(2) 0.0595(10) Uani 1 1 d . . . H6B1 H 0.6817 1.3229 0.1798 0.071 Uiso 1 1 calc R . . H6B2 H 0.6983 1.4018 0.0979 0.071 Uiso 1 1 calc R . . C8A C -0.07464(18) 1.2507(3) 0.11585(18) 0.0410(7) Uani 1 1 d . . . H8A1 H -0.1211 1.2589 0.1539 0.049 Uiso 1 1 calc R . . H8A2 H -0.0397 1.1787 0.1340 0.049 Uiso 1 1 calc R . . C8B C 0.61508(19) 1.5299(3) 0.20195(19) 0.0545(9) Uani 1 1 d . . . H8B1 H 0.6608 1.5787 0.1785 0.065 Uiso 1 1 calc R . . H8B2 H 0.6379 1.4920 0.2550 0.065 Uiso 1 1 calc R . . C18A C 0.11055(18) 1.7675(3) -0.02758(19) 0.0414(7) Uani 1 1 d . . . H18A H 0.1454 1.8432 -0.0238 0.050 Uiso 1 1 calc R . . H18B H 0.0641 1.7766 0.0104 0.050 Uiso 1 1 calc R . . C18B C 0.4573(2) 1.3882(3) -0.21836(18) 0.0556(9) Uani 1 1 d . . . H18C H 0.4394 1.3259 -0.2611 0.067 Uiso 1 1 calc R . . H18D H 0.5041 1.4372 -0.2397 0.067 Uiso 1 1 calc R . . C20A C 0.39572(19) 1.4200(3) 0.0485(2) 0.0523(9) Uani 1 1 d . . . H20A H 0.4238 1.4960 0.0406 0.063 Uiso 1 1 calc R . . C20B C 0.14153(17) 1.4116(3) -0.08255(18) 0.0406(7) Uani 1 1 d . . . H20B H 0.1486 1.4921 -0.1043 0.049 Uiso 1 1 calc R . . C22A C 0.32104(18) 1.2769(3) 0.10187(19) 0.0472(8) Uani 1 1 d . . . H22A H 0.2866 1.2341 0.1387 0.057 Uiso 1 1 calc R . . C22B C 0.11456(18) 1.2609(3) 0.00033(19) 0.0468(8) Uani 1 1 d . . . H22B H 0.0989 1.2169 0.0482 0.056 Uiso 1 1 calc R . . C23A C 0.3479(2) 1.2348(3) 0.0305(2) 0.0564(9) Uani 1 1 d . . . H23A H 0.3368 1.1559 0.0067 0.068 Uiso 1 1 calc R . . C23B C 0.13732(18) 1.2125(3) -0.0708(2) 0.0482(8) Uani 1 1 d . . . H23B H 0.1412 1.1273 -0.0836 0.058 Uiso 1 1 calc R . . O1A O 0.16135(11) 1.66299(16) -0.00361(11) 0.0370(5) Uani 1 1 d . . . O1B O 0.48515(12) 1.32916(19) -0.14214(12) 0.0439(5) Uani 1 1 d . . . O4A O 0.10985(11) 1.52845(17) 0.14080(11) 0.0383(5) Uani 1 1 d . . . O4B O 0.59952(12) 1.29350(18) -0.00947(13) 0.0442(5) Uani 1 1 d . . . O7A O -0.02390(11) 1.35950(17) 0.11938(11) 0.0358(4) Uani 1 1 d . . . O7B O 0.58728(12) 1.4367(2) 0.14449(13) 0.0478(5) Uani 1 1 d . . . O101 O 0.27374(18) 1.3503(2) 0.28513(15) 0.0751(8) Uani 1 1 d . . . O102 O 0.32643(13) 1.54410(19) 0.25356(13) 0.0521(6) Uani 1 1 d . . . O103 O 0.24028(14) 1.5211(2) 0.36459(15) 0.0677(7) Uani 1 1 d . . . O104 O 0.37730(17) 1.4450(3) 0.37422(17) 0.0830(8) Uani 1 1 d . . . O105 O 0.17674(14) 1.36163(18) -0.29602(12) 0.0497(5) Uani 1 1 d . . . O106 O 0.23246(13) 1.5054(2) -0.38447(14) 0.0562(6) Uani 1 1 d . . . O107 O 0.17477(13) 1.57020(19) -0.26042(13) 0.0540(6) Uani 1 1 d . . . O108 O 0.08638(13) 1.4976(2) -0.37227(14) 0.0606(6) Uani 1 1 d . . . N27A N 0.39430(16) 1.3263(3) -0.00190(15) 0.0533(7) Uani 1 1 d . . . H27A H 0.4193 1.3226 -0.0493 0.064 Uiso 1 1 calc R . . N27B N 0.15393(14) 1.3078(2) -0.12197(14) 0.0422(6) Uani 1 1 d . . . H27B H 0.1704 1.3012 -0.1732 0.051 Uiso 1 1 calc R . . N29A N 0.35175(15) 1.3914(2) 0.11215(15) 0.0452(6) Uani 1 1 d . . . H29A H 0.3436 1.4398 0.1550 0.054 Uiso 1 1 calc R . . N29B N 0.11780(14) 1.3846(2) -0.00822(15) 0.0416(6) Uani 1 1 d . . . H29B H 0.1058 1.4385 0.0303 0.050 Uiso 1 1 calc R . . Cl1 Cl 0.30429(5) 1.46420(6) 0.32027(4) 0.04042(19) Uani 1 1 d . . . Cl2 Cl 0.16745(4) 1.48509(6) -0.32868(4) 0.03465(18) 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 C2A 0.0392(16) 0.0400(17) 0.0479(19) -0.0105(15) 0.0000(14) -0.0039(13) C2B 0.0505(19) 0.0446(19) 0.065(2) -0.0176(17) 0.0267(16) -0.0076(15) C3A 0.0468(17) 0.0398(18) 0.0419(18) -0.0135(14) 0.0014(14) 0.0018(13) C3B 0.0482(19) 0.0313(17) 0.085(3) -0.0007(18) 0.0238(17) 0.0021(14) C5A 0.0426(16) 0.055(2) 0.0226(14) -0.0073(13) 0.0054(12) 0.0065(14) C5B 0.059(2) 0.056(2) 0.070(3) 0.027(2) 0.0088(18) 0.0202(18) C6A 0.0443(16) 0.0475(18) 0.0272(15) 0.0007(14) 0.0066(12) 0.0084(14) C6B 0.0422(18) 0.081(3) 0.055(2) 0.022(2) -0.0010(15) 0.0177(18) C8A 0.0494(17) 0.0324(16) 0.0425(18) 0.0073(14) 0.0116(14) 0.0009(13) C8B 0.0443(18) 0.083(3) 0.0355(17) 0.0099(18) -0.0049(14) -0.0121(17) C18A 0.0437(16) 0.0305(16) 0.0507(19) -0.0012(14) 0.0092(14) -0.0019(13) C18B 0.055(2) 0.083(3) 0.0295(17) -0.0037(17) 0.0044(14) -0.0177(18) C20A 0.0441(18) 0.0440(19) 0.070(2) 0.0161(19) 0.0144(17) -0.0020(15) C20B 0.0417(16) 0.0357(17) 0.0439(19) 0.0028(15) 0.0003(14) -0.0020(13) C22A 0.0453(17) 0.053(2) 0.0440(19) 0.0075(16) 0.0104(14) -0.0094(15) C22B 0.0483(18) 0.048(2) 0.0451(19) 0.0127(16) 0.0125(14) 0.0094(15) C23A 0.061(2) 0.050(2) 0.058(2) -0.0143(18) -0.0021(17) -0.0037(17) C23B 0.0499(18) 0.0312(17) 0.066(2) -0.0048(16) 0.0202(16) 0.0056(14) O1A 0.0392(11) 0.0328(11) 0.0395(11) -0.0048(9) 0.0055(9) 0.0030(8) O1B 0.0453(12) 0.0502(13) 0.0380(12) -0.0051(10) 0.0160(9) -0.0022(9) O4A 0.0433(11) 0.0408(12) 0.0317(10) -0.0086(9) 0.0084(8) -0.0003(9) O4B 0.0443(11) 0.0333(11) 0.0554(14) 0.0089(10) 0.0077(10) 0.0054(9) O7A 0.0437(11) 0.0373(11) 0.0267(10) 0.0033(8) 0.0042(8) -0.0014(9) O7B 0.0353(11) 0.0615(14) 0.0461(13) 0.0088(11) -0.0014(9) 0.0004(10) O101 0.126(2) 0.0441(14) 0.0607(16) -0.0206(12) 0.0467(15) -0.0433(14) O102 0.0710(14) 0.0423(13) 0.0446(13) 0.0094(10) 0.0167(11) -0.0151(10) O103 0.0641(15) 0.0641(16) 0.0800(17) -0.0300(13) 0.0430(13) -0.0223(12) O104 0.0836(18) 0.082(2) 0.0796(19) 0.0201(16) -0.0190(15) 0.0114(15) O105 0.0804(15) 0.0289(11) 0.0417(12) 0.0079(9) 0.0184(11) 0.0039(10) O106 0.0608(14) 0.0506(14) 0.0611(15) 0.0146(11) 0.0316(11) 0.0042(11) O107 0.0637(14) 0.0442(13) 0.0533(14) -0.0211(11) -0.0023(11) 0.0061(10) O108 0.0490(13) 0.0753(17) 0.0551(14) -0.0037(13) -0.0137(11) 0.0041(11) N27A 0.0520(16) 0.079(2) 0.0312(14) 0.0106(15) 0.0161(12) 0.0170(15) N27B 0.0435(14) 0.0565(17) 0.0278(13) -0.0100(12) 0.0116(10) -0.0043(12) N29A 0.0466(14) 0.0491(17) 0.0406(15) -0.0028(13) 0.0094(12) 0.0019(12) N29B 0.0447(14) 0.0455(16) 0.0353(14) -0.0131(12) 0.0074(11) 0.0101(11) Cl1 0.0526(4) 0.0350(4) 0.0352(4) -0.0021(3) 0.0147(3) -0.0098(3) Cl2 0.0402(4) 0.0306(4) 0.0336(4) 0.0019(3) 0.0057(3) 0.0014(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 C2A O1A 1.433(3) . ? C2A C3A 1.497(4) . ? C2B O1B 1.425(4) . ? C2B C3B 1.492(5) . ? C3A O4A 1.431(3) . ? C3B O4B 1.421(4) . ? C5A O4A 1.428(3) . ? C5A C6A 1.484(4) . ? C5B O4B 1.421(4) . ? C5B C6B 1.482(5) . ? C6A O7A 1.426(3) . ? C6B O7B 1.428(4) . ? C8A O7A 1.427(3) . ? C8A C18A 1.500(4) 3_585 ? C8B O7B 1.418(4) . ? C8B C18B 1.488(5) 3_685 ? C18A O1A 1.429(3) . ? C18A C8A 1.500(4) 3_585 ? C18B O1B 1.422(4) . ? C18B C8B 1.488(5) 3_685 ? C20A N27A 1.297(4) . ? C20A N29A 1.309(4) . ? C20B N29B 1.305(3) . ? C20B N27B 1.313(4) . ? C22A C23A 1.326(4) . ? C22A N29A 1.341(4) . ? C22B C23B 1.326(4) . ? C22B N29B 1.352(4) . ? C23A N27A 1.360(4) . ? C23B N27B 1.356(4) . ? O101 Cl1 1.430(2) . ? O102 Cl1 1.437(2) . ? O103 Cl1 1.417(2) . ? O104 Cl1 1.411(3) . ? O105 Cl2 1.443(2) . ? O106 Cl2 1.424(2) . ? O107 Cl2 1.430(2) . ? O108 Cl2 1.425(2) . ? 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 O1A C2A C3A 113.6(2) . . ? O1B C2B C3B 107.7(2) . . ? O4A C3A C2A 109.3(2) . . ? O4B C3B C2B 108.5(2) . . ? O4A C5A C6A 110.2(2) . . ? O4B C5B C6B 111.0(3) . . ? O7A C6A C5A 109.2(2) . . ? O7B C6B C5B 110.3(3) . . ? O7A C8A C18A 108.8(2) . 3_585 ? O7B C8B C18B 109.4(2) . 3_685 ? O1A C18A C8A 108.6(2) . 3_585 ? O1B C18B C8B 108.4(2) . 3_685 ? N27A C20A N29A 108.1(3) . . ? N29B C20B N27B 107.9(3) . . ? C23A C22A N29A 106.9(3) . . ? C23B C22B N29B 107.0(3) . . ? C22A C23A N27A 106.9(3) . . ? C22B C23B N27B 106.9(3) . . ? C18A O1A C2A 113.0(2) . . ? C18B O1B C2B 114.4(2) . . ? C5A O4A C3A 111.7(2) . . ? C5B O4B C3B 112.0(2) . . ? C6A O7A C8A 112.5(2) . . ? C8B O7B C6B 111.4(2) . . ? C20A N27A C23A 108.8(3) . . ? C20B N19B C23B 108.9(2) . . ? C20A N29A C22A 109.4(3) . . ? C20B N29B C22B 109.3(2) . . ? O104 Cl1 O103 109.98(17) . . ? O104 Cl1 O101 110.77(17) . . ? O103 Cl1 O101 109.86(14) . . ? O104 Cl1 O102 108.24(15) . . ? O103 Cl1 O102 109.10(15) . . ? O101 Cl1 O102 108.84(13) . . ? O106 Cl2 O108 110.06(14) . . ? O106 Cl2 O107 110.74(14) . . ? O108 Cl2 O107 109.65(13) . . ? O106 Cl2 O105 108.11(12) . . ? O108 Cl2 O105 109.43(14) . . ? O107 Cl2 O105 108.82(13) . . ? 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 O1A C2A C3A O4A 62.7(3) . . . . ? O1B C2B C3B O4B -59.0(3) . . . . ? O4A C5A C6A O7A -61.5(3) . . . . ? O4B C5B C6B O7B 71.2(3) . . . . ? N29A C22A C23A N27A -0.6(4) . . . . ? N29B C22B C23B N27B -0.2(3) . . . . ? C8A C18A O1A C2A 178.2(2) 3_585 . . . ? C3A C2A O1A C18A 75.7(3) . . . . ? C8B C18B O1B C2B 178.6(2) 3_685 . . . ? C3B C2B O1B C18B 178.5(2) . . . . ? C6A C5A O4A C3A -179.9(2) . . . . ? C2A C3A O4A C5A 177.8(2) . . . . ? C6B C5B O4B C3B 174.1(2) . . . . ? C2B C3B O4B C5B -179.8(2) . . . . ? C5A C6A O7A C8A -164.4(2) . . . . ? C18A C8A O7A C6A -170.4(2) 3_585 . . . ? C18B C8B O7B C6B 180.0(3) 3_685 . . . ? C5B C6B O7B C8B 174.5(3) . . . . ? N29A C20A N27A C23A 0.0(4) . . . . ? C22A C23A N27A C20A 0.3(4) . . . . ? N29B C20B N27B C23B 0.1(3) . . . . ? C22B C23B N27B C20B 0.0(3) . . . . ? N27A C20A N29A C22A -0.4(4) . . . . ? C23A C22A N29A C20A 0.6(4) . . . . ? N27B C20B N29B C22B -0.2(3) . . . . ? C23B C22B N29B C20B 0.2(3) . . . . ? 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 N27A H27A O1B 0.88 1.87 2.746(3) 171.5 . N27B H27B O105 0.88 2.08 2.893(3) 153.0 . N27B H27B O101 0.88 2.44 3.022(3) 123.7 4_585 N29A H29A O102 0.88 1.98 2.856(3) 178.2 . N29A H29A O101 0.88 2.61 3.139(3) 119.4 . N29B H29B O4A 0.88 2.02 2.861(3) 160.1 . N29B H29B O1A 0.88 2.66 3.100(3) 112.1 . _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.86 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.247 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.062 #===END data_comp10 _audit_creation_method ? _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 O7 (C3 H5 N2)+ (Cl O4)-' _chemical_formula_sum 'C25 H33 Cl N2 O11' _chemical_formula_weight 572.98 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'Cl' 'Cl' 0.1484 0.1585 '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' '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' _symmetry_cell_setting 'orthorhombic' _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 8.392(1) _cell_length_b 12.611(2) _cell_length_c 25.993(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2750.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173.0(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.384 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1208 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type 'none' _exptl_absorpt_correction_T_min 0.9061 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173.0(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 '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 2922 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1745 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.55 _reflns_number_total 2922 _reflns_number_gt 1410 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1104P)^2^+0.0000P] 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 -0.2(2) _refine_ls_number_reflns 2922 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2024 _refine_ls_R_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.2243 _refine_ls_wR_factor_gt 0.1857 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 O1 O -0.9914(7) -1.0719(6) -0.0579(3) 0.0536(19) Uani 1 1 d . . . O4 O -0.8944(8) -0.9393(7) -0.1468(2) 0.056(2) Uani 1 1 d . . . O7 O -0.9675(7) -0.7211(6) -0.1691(3) 0.0529(19) Uani 1 1 d . . . O14 O -1.2067(7) -0.6143(5) -0.1351(3) 0.0515(19) Uani 1 1 d . A . O17 O -1.4174(8) -0.6781(7) -0.0551(4) 0.082(3) Uani 1 1 d . . . O20 O -1.4294(8) -0.8703(6) 0.0105(3) 0.067(2) Uani 1 1 d . A . O23 O -1.2204(7) -1.0473(6) 0.0073(2) 0.0517(19) Uani 1 1 d . . . C2 C -0.8829(12) -1.0983(8) -0.0982(4) 0.054(3) Uani 1 1 d . . . H2A H -0.8765 -1.1764 -0.1015 0.065 Uiso 1 1 calc R . . H2B H -0.7754 -1.0717 -0.0892 0.065 Uiso 1 1 calc R . . C3 C -0.9322(12) -1.0525(10) -0.1476(4) 0.062(3) Uani 1 1 d . . . H3A H -0.8750 -1.0878 -0.1762 0.074 Uiso 1 1 calc R . . H3B H -1.0481 -1.0629 -0.1527 0.074 Uiso 1 1 calc R . . C5 C -0.8937(12) -0.8947(8) -0.1965(4) 0.049(3) Uani 1 1 d . . . H5A H -1.0016 -0.8999 -0.2117 0.059 Uiso 1 1 calc R . . H5B H -0.8192 -0.9347 -0.2188 0.059 Uiso 1 1 calc R . . C6 C -0.8446(12) -0.7824(9) -0.1944(5) 0.061(3) Uani 1 1 d . . . H6A H -0.7432 -0.7759 -0.1752 0.074 Uiso 1 1 calc R . . H6B H -0.8274 -0.7552 -0.2297 0.074 Uiso 1 1 calc R . . C8 C -0.9513(10) -0.6154(9) -0.1718(4) 0.045(3) Uani 1 1 d . . . C9 C -0.8185(12) -0.5613(11) -0.1899(4) 0.054(3) Uani 1 1 d . . . H9 H -0.7277 -0.6000 -0.2011 0.065 Uiso 1 1 calc R . . C10 C -0.8168(12) -0.4528(11) -0.1917(4) 0.058(3) Uani 1 1 d . . . H10 H -0.7248 -0.4178 -0.2046 0.069 Uiso 1 1 calc R . . C11 C -0.9438(14) -0.3934(10) -0.1757(4) 0.061(3) Uani 1 1 d . . . H11 H -0.9400 -0.3181 -0.1771 0.073 Uiso 1 1 calc R . . C12 C -1.0842(12) -0.4475(10) -0.1565(4) 0.056(3) Uani 1 1 d . . . H12 H -1.1756 -0.4086 -0.1460 0.067 Uiso 1 1 calc R . . C13 C -1.0820(11) -0.5561(10) -0.1539(4) 0.050(3) Uani 1 1 d . . . C15 C -1.3505(11) -0.5569(9) -0.1214(4) 0.057(3) Uani 1 1 d . . . H15A H -1.3937 -0.5193 -0.1518 0.069 Uiso 1 1 calc R A . H15B H -1.3275 -0.5042 -0.0942 0.069 Uiso 1 1 calc R . . C16 C -1.4686(12) -0.6381(11) -0.1022(5) 0.074(4) Uani 1 1 d . A . H16A H -1.5747 -0.6048 -0.0982 0.088 Uiso 1 1 calc R . . H16B H -1.4780 -0.6965 -0.1275 0.088 Uiso 1 1 calc R . . C18 C -1.518(2) -0.7047(19) -0.0088(10) 0.061(5) Uani 0.596(19) 1 d P A 1 H18A H -1.4615 -0.6805 0.0225 0.073 Uiso 0.596(19) 1 calc PR A 1 H18B H -1.6191 -0.6644 -0.0110 0.073 Uiso 0.596(19) 1 calc PR A 1 C18B C -1.556(4) -0.741(3) -0.0415(14) 0.061(5) Uani 0.404(19) 1 d P A 2 H18C H -1.6465 -0.6920 -0.0361 0.073 Uiso 0.404(19) 1 calc PR A 2 H18D H -1.5835 -0.7857 -0.0717 0.073 Uiso 0.404(19) 1 calc PR A 2 C19 C -1.5500(17) -0.8002(15) -0.0039(9) 0.171(11) Uani 1 1 d . . . H19A H -1.5938 -0.8253 -0.0371 0.205 Uiso 1 1 calc R A 1 H19B H -1.6364 -0.8063 0.0219 0.205 Uiso 1 1 calc R A 1 C21 C -1.4803(11) -0.9755(9) 0.0161(4) 0.057(3) Uani 1 1 d . . . H21A H -1.5041 -1.0056 -0.0182 0.069 Uiso 1 1 calc R A . H21B H -1.5795 -0.9771 0.0367 0.069 Uiso 1 1 calc R . . C22 C -1.3582(11) -1.0408(9) 0.0415(4) 0.050(3) Uani 1 1 d . A . H22A H -1.3269 -1.0083 0.0747 0.060 Uiso 1 1 calc R . . H22B H -1.4006 -1.1127 0.0485 0.060 Uiso 1 1 calc R . . C24 C -1.0896(11) -1.1069(8) 0.0258(4) 0.048(3) Uani 1 1 d . . . C25 C -1.0791(11) -1.1492(8) 0.0731(4) 0.050(3) Uani 1 1 d . . . H25 H -1.1632 -1.1402 0.0971 0.060 Uiso 1 1 calc R . . C26 C -0.9414(12) -1.2072(9) 0.0865(4) 0.061(3) Uani 1 1 d . . . H26 H -0.9326 -1.2393 0.1194 0.074 Uiso 1 1 calc R . . C27 C -0.8214(13) -1.2165(9) 0.0515(5) 0.057(3) Uani 1 1 d . . . H27 H -0.7274 -1.2534 0.0612 0.069 Uiso 1 1 calc R . . C28 C -0.8306(10) -1.1744(8) 0.0024(4) 0.044(2) Uani 1 1 d . . . H28 H -0.7471 -1.1854 -0.0217 0.053 Uiso 1 1 calc R . . C29 C -0.9668(11) -1.1149(8) -0.0111(4) 0.044(3) Uani 1 1 d . . . N30 N -1.2725(9) -0.9452(7) -0.0941(3) 0.050(2) Uani 1 1 d . . . H30 H -1.2430 -0.9702 -0.0639 0.060 Uiso 1 1 calc R . . N32 N -1.2845(9) -0.8500(6) -0.1613(3) 0.047(2) Uani 1 1 d . . . H32 H -1.2644 -0.7997 -0.1838 0.056 Uiso 1 1 calc R . . C31 C -1.2201(11) -0.8589(8) -0.1155(4) 0.043(3) Uani 1 1 d . . . H31 H -1.1471 -0.8103 -0.1005 0.052 Uiso 1 1 calc R . . C33 C -1.3884(12) -0.9326(9) -0.1679(4) 0.054(3) Uani 1 1 d . . . H33 H -1.4538 -0.9458 -0.1971 0.064 Uiso 1 1 calc R . . C34 C -1.3795(12) -0.9898(10) -0.1260(4) 0.057(3) Uani 1 1 d . . . H34 H -1.4389 -1.0524 -0.1192 0.069 Uiso 1 1 calc R . . Cl1 Cl -1.4020(3) -0.6776(3) -0.26726(11) 0.0585(8) Uani 1 1 d . . . O100 O -1.3947(8) -0.6675(7) -0.3216(3) 0.072(2) Uani 1 1 d . . . O101 O -1.2440(7) -0.7098(6) -0.2479(3) 0.063(2) Uani 1 1 d . . . O102 O -1.5117(10) -0.7548(8) -0.2534(4) 0.111(4) Uani 1 1 d . . . O103 O -1.4447(10) -0.5777(6) -0.2445(3) 0.092(3) 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 O1 0.048(4) 0.070(5) 0.043(4) 0.002(4) 0.007(3) 0.009(4) O4 0.049(4) 0.080(6) 0.039(5) 0.007(4) 0.000(3) 0.013(4) O7 0.039(4) 0.045(5) 0.074(5) -0.003(4) 0.005(4) 0.002(4) O14 0.037(4) 0.046(5) 0.072(5) 0.000(4) 0.004(3) 0.005(4) O17 0.053(4) 0.086(6) 0.106(6) 0.035(6) 0.028(5) 0.019(5) O20 0.061(5) 0.049(5) 0.091(6) 0.016(4) 0.014(4) 0.007(5) O23 0.038(4) 0.067(5) 0.050(4) 0.000(4) 0.002(3) 0.002(4) C2 0.065(7) 0.043(7) 0.054(7) 0.004(6) 0.026(6) 0.008(6) C3 0.062(7) 0.060(8) 0.064(8) 0.016(7) 0.018(6) 0.006(7) C5 0.045(6) 0.058(8) 0.045(7) -0.010(6) 0.012(5) -0.003(6) C6 0.039(6) 0.070(9) 0.075(9) 0.014(7) 0.010(6) 0.010(6) C8 0.032(6) 0.054(8) 0.049(7) -0.015(6) -0.002(5) -0.007(6) C9 0.049(7) 0.065(10) 0.047(7) -0.006(6) -0.004(5) 0.001(7) C10 0.040(6) 0.067(10) 0.066(8) 0.000(7) 0.004(6) -0.012(6) C11 0.091(9) 0.065(8) 0.028(6) -0.003(6) -0.010(6) -0.027(8) C12 0.049(6) 0.067(9) 0.052(7) -0.012(7) 0.003(6) -0.004(7) C13 0.041(6) 0.062(8) 0.048(7) -0.005(6) -0.006(5) -0.012(7) C15 0.050(7) 0.052(7) 0.070(8) -0.007(7) -0.009(5) 0.005(6) C16 0.025(5) 0.098(11) 0.098(10) -0.003(9) 0.008(6) 0.004(6) C18 0.058(11) 0.058(15) 0.066(16) -0.001(12) 0.017(11) 0.026(10) C18B 0.058(11) 0.058(15) 0.066(16) -0.001(12) 0.017(11) 0.026(10) C19 0.072(10) 0.147(18) 0.29(3) 0.144(19) 0.096(13) 0.057(12) C21 0.042(6) 0.078(10) 0.051(7) -0.003(7) 0.010(5) 0.016(6) C22 0.050(6) 0.043(7) 0.058(7) 0.006(6) 0.015(5) -0.007(5) C24 0.040(6) 0.050(7) 0.055(7) 0.000(6) -0.004(5) 0.001(6) C25 0.044(6) 0.061(8) 0.045(7) 0.009(6) 0.004(5) -0.006(6) C26 0.053(7) 0.080(9) 0.051(7) 0.003(6) -0.006(6) -0.007(6) C27 0.057(7) 0.051(8) 0.065(8) -0.013(7) -0.005(6) 0.005(6) C28 0.042(6) 0.043(6) 0.048(7) 0.004(6) 0.006(5) 0.002(5) C29 0.049(6) 0.049(7) 0.035(6) 0.006(6) 0.007(5) 0.000(5) N30 0.044(5) 0.058(6) 0.048(5) 0.016(5) 0.002(4) 0.012(5) N32 0.056(5) 0.036(5) 0.049(6) 0.008(5) -0.002(4) -0.002(4) C31 0.049(6) 0.036(7) 0.044(7) 0.003(6) -0.001(5) -0.005(5) C33 0.052(6) 0.064(8) 0.044(7) -0.010(7) -0.008(5) -0.003(7) C34 0.045(6) 0.073(9) 0.055(7) 0.010(7) -0.006(6) -0.019(6) Cl1 0.0476(16) 0.068(2) 0.0601(19) 0.0091(17) 0.0047(14) 0.0044(16) O100 0.048(4) 0.112(7) 0.055(5) 0.001(5) -0.009(4) -0.004(5) O101 0.044(4) 0.080(6) 0.065(5) 0.011(4) -0.006(3) 0.011(4) O102 0.046(5) 0.125(8) 0.161(9) 0.050(8) 0.023(5) 0.000(5) O103 0.113(7) 0.065(6) 0.097(7) -0.010(5) -0.012(5) 0.038(5) _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 O1 C29 1.348(11) . ? O1 C2 1.427(10) . ? O4 C5 1.410(11) . ? O4 C3 1.463(13) . ? O7 C8 1.342(12) . ? O7 C6 1.447(12) . ? O14 C13 1.368(11) . ? O14 C15 1.452(11) . ? O17 C16 1.394(14) . ? O17 C18B 1.46(3) . ? O17 C18 1.51(2) . ? O20 C19 1.395(16) . ? O20 C21 1.401(12) . ? O23 C24 1.415(11) . ? O23 C22 1.462(10) . ? C2 C3 1.467(13) . ? C5 C6 1.475(14) . ? C8 C9 1.388(14) . ? C8 C13 1.407(14) . ? C9 C10 1.369(15) . ? C10 C11 1.368(15) . ? C11 C12 1.451(14) . ? C12 C13 1.372(15) . ? C15 C16 1.509(15) . ? C18 C19 1.24(2) . ? C18B C19 1.23(3) . ? C21 C22 1.471(13) . ? C24 C25 1.343(13) . ? C24 C29 1.412(13) . ? C25 C26 1.411(14) . ? C26 C27 1.362(14) . ? C27 C28 1.385(14) . ? C28 C29 1.412(12) . ? N30 C31 1.300(11) . ? N30 C34 1.345(12) . ? N32 C31 1.311(12) . ? N32 C33 1.370(12) . ? C33 C34 1.309(13) . ? Cl1 O102 1.387(9) . ? Cl1 O100 1.419(7) . ? Cl1 O103 1.437(8) . ? Cl1 O101 1.475(7) . ? 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 C29 O1 C2 118.0(7) . . ? C5 O4 C3 112.2(8) . . ? C8 O7 C6 115.8(8) . . ? C13 O14 C15 117.1(8) . . ? C16 O17 C18B 99.5(16) . . ? C16 O17 C18 127.6(11) . . ? C18B O17 C18 40.2(13) . . ? C19 O20 C21 114.0(10) . . ? C24 O23 C22 115.9(7) . . ? O1 C2 C3 111.7(8) . . ? O4 C3 C2 108.1(9) . . ? O4 C5 C6 110.5(9) . . ? O7 C6 C5 109.3(8) . . ? O7 C8 C9 125.9(10) . . ? O7 C8 C13 115.6(9) . . ? C9 C8 C13 118.5(10) . . ? C10 C9 C8 120.7(11) . . ? C11 C10 C9 122.0(11) . . ? C10 C11 C12 118.7(11) . . ? C13 C12 C11 118.4(10) . . ? O14 C13 C12 122.9(10) . . ? O14 C13 C8 115.4(10) . . ? C12 C13 C8 121.7(10) . . ? O14 C15 C16 106.8(8) . . ? O17 C16 C15 109.5(9) . . ? C19 C18 O17 114.7(19) . . ? C19 C18B O17 119(3) . . ? C18B C19 C18 48.9(16) . . ? C18B C19 O20 128.9(19) . . ? C18 C19 O20 119.1(18) . . ? O20 C21 C22 111.4(9) . . ? O23 C22 C21 108.0(8) . . ? C25 C24 C29 123.1(10) . . ? C25 C24 O23 125.0(9) . . ? C29 C24 O23 111.9(9) . . ? C24 C25 C26 119.1(10) . . ? C27 C26 C25 119.0(10) . . ? C26 C27 C28 122.8(10) . . ? C27 C28 C29 118.6(9) . . ? O1 C29 C28 124.3(9) . . ? O1 C29 C24 118.2(9) . . ? C28 C29 C24 117.4(9) . . ? C31 N30 C34 108.1(9) . . ? C31 N32 C33 108.1(9) . . ? N30 C31 N32 108.7(9) . . ? C34 C33 N32 106.1(9) . . ? C33 C34 N30 108.7(10) . . ? O102 Cl1 O100 110.5(6) . . ? O102 Cl1 O103 110.1(6) . . ? O100 Cl1 O103 110.0(6) . . ? O102 Cl1 O101 108.3(5) . . ? O100 Cl1 O101 109.0(4) . . ? O103 Cl1 O101 109.0(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 C29 O1 C2 C3 175.4(9) . . . . ? C5 O4 C3 C2 162.8(8) . . . . ? O1 C2 C3 O4 75.9(10) . . . . ? C3 O4 C5 C6 -176.2(8) . . . . ? C8 O7 C6 C5 -169.6(9) . . . . ? O4 C5 C6 O7 -68.6(11) . . . . ? C6 O7 C8 C9 -9.7(15) . . . . ? C6 O7 C8 C13 171.1(8) . . . . ? O7 C8 C9 C10 178.7(10) . . . . ? C13 C8 C9 C10 -2.1(16) . . . . ? C8 C9 C10 C11 0.6(17) . . . . ? C9 C10 C11 C12 -0.4(17) . . . . ? C10 C11 C12 C13 1.8(15) . . . . ? C15 O14 C13 C12 5.0(14) . . . . ? C15 O14 C13 C8 -173.5(8) . . . . ? C11 C12 C13 O14 178.2(8) . . . . ? C11 C12 C13 C8 -3.4(15) . . . . ? O7 C8 C13 O14 1.4(13) . . . . ? C9 C8 C13 O14 -177.9(8) . . . . ? O7 C8 C13 C12 -177.1(9) . . . . ? C9 C8 C13 C12 3.6(16) . . . . ? C13 O14 C15 C16 179.7(8) . . . . ? C18B O17 C16 C15 172.7(16) . . . . ? C18 O17 C16 C15 140.7(15) . . . . ? O14 C15 C16 O17 69.4(11) . . . . ? C16 O17 C18 C19 100(2) . . . . ? C18B O17 C18 C19 46(2) . . . . ? C16 O17 C18B C19 172(3) . . . . ? C18 O17 C18B C19 -49(3) . . . . ? O17 C18B C19 C18 52(3) . . . . ? O17 C18B C19 O20 -46(5) . . . . ? O17 C18 C19 C18B -47(2) . . . . ? O17 C18 C19 O20 71(3) . . . . ? C21 O20 C19 C18B -123(3) . . . . ? C21 O20 C19 C18 178.4(19) . . . . ? C19 O20 C21 C22 -168.0(13) . . . . ? C24 O23 C22 C21 179.6(8) . . . . ? O20 C21 C22 O23 -65.8(11) . . . . ? C22 O23 C24 C25 -5.7(14) . . . . ? C22 O23 C24 C29 175.9(8) . . . . ? C29 C24 C25 C26 -1.9(16) . . . . ? O23 C24 C25 C26 179.9(9) . . . . ? C24 C25 C26 C27 1.6(16) . . . . ? C25 C26 C27 C28 -2.3(17) . . . . ? C26 C27 C28 C29 3.3(16) . . . . ? C2 O1 C29 C28 7.8(14) . . . . ? C2 O1 C29 C24 -167.4(9) . . . . ? C27 C28 C29 O1 -178.5(10) . . . . ? C27 C28 C29 C24 -3.3(14) . . . . ? C25 C24 C29 O1 178.3(10) . . . . ? O23 C24 C29 O1 -3.3(13) . . . . ? C25 C24 C29 C28 2.8(15) . . . . ? O23 C24 C29 C28 -178.8(8) . . . . ? C34 N30 C31 N32 -3.2(11) . . . . ? C33 N32 C31 N30 2.9(11) . . . . ? C31 N32 C33 C34 -1.5(11) . . . . ? N32 C33 C34 N30 -0.5(12) . . . . ? C31 N30 C34 C33 2.3(12) . . . . ? 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 N30 H30 O23 0.88 2.10 2.965(10) 167.5 . N30 H30 O1 0.88 2.48 2.999(10) 118.8 . N32 H32 O101 0.88 2.02 2.883(11) 165.7 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.55 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.335 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.072 #===END data_COMP7 _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 C c 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_COMP14 _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 C c 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 #===END