# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Juyoung Yoon' _publ_contact_author_email JYOON@EWHA.AC.KR loop_ _publ_author_name 'Juyoung Yoon.' 'Ha Na Kim.' 'Youngmee Kim.' 'Sung-Jin Kim.' 'Jung Huyn Soh.' K.M.K.Swamy data_SW206 _database_code_depnum_ccdc_archive 'CCDC 707406' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 Cl2 N2 O7 S2' _chemical_formula_weight 695.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 8.7630(18) _cell_length_b 14.817(3) _cell_length_c 13.295(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.06(3) _cell_angle_gamma 90.00 _cell_volume 1725.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 681 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 17.96 _exptl_crystal_description Plate _exptl_crystal_colour Orange _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.357 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8805 _diffrn_reflns_av_R_equivalents 0.0782 _diffrn_reflns_av_sigmaI/netI 0.2335 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3105 _reflns_number_gt 1575 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0991P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3105 _refine_ls_number_parameters 219 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1659 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1674 _refine_ls_wR_factor_gt 0.1499 _refine_ls_goodness_of_fit_ref 0.771 _refine_ls_restrained_S_all 0.771 _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 0.3159(2) -0.09794(11) 0.45533(15) 0.0575(6) Uani 1 1 d . . . S1 S 1.0472(2) -0.02468(15) 0.17460(19) 0.0780(8) Uani 1 1 d . . . N1 N 0.7023(6) 0.0350(3) 0.1895(4) 0.0388(14) Uani 1 1 d . . . O1 O 0.0816(7) 0.2500 0.3776(5) 0.0449(17) Uani 1 2 d S . . O2 O -0.1651(7) 0.2500 0.4210(5) 0.0447(17) Uani 1 2 d S . . O3 O 0.4475(6) 0.2500 0.2680(4) 0.0405(16) Uani 1 2 d S . . O4 O 0.5095(5) -0.0668(3) 0.2850(4) 0.0552(14) Uani 1 1 d . . . H4 H 0.5767 -0.0547 0.2457 0.083 Uiso 1 1 calc R . . C1 C -0.0309(13) 0.2500 0.4454(7) 0.039(2) Uani 1 2 d S . . C2 C 0.0422(10) 0.2500 0.5472(7) 0.035(2) Uani 1 2 d S . . C3 C -0.0251(12) 0.2500 0.6409(8) 0.046(3) Uani 1 2 d S . . H3 H -0.1306 0.2500 0.6459 0.055 Uiso 1 2 calc SR . . C4 C 0.0693(11) 0.2500 0.7247(7) 0.043(3) Uani 1 2 d S . . H4A H 0.0285 0.2500 0.7883 0.052 Uiso 1 2 calc SR . . C5 C 0.2305(11) 0.2500 0.7147(8) 0.048(3) Uani 1 2 d S . . H5 H 0.2935 0.2500 0.7725 0.057 Uiso 1 2 calc SR . . C6 C 0.2949(11) 0.2500 0.6239(7) 0.041(2) Uani 1 2 d S . . H6 H 0.4004 0.2500 0.6183 0.049 Uiso 1 2 calc SR . . C7 C 0.1974(10) 0.2500 0.5388(7) 0.035(2) Uani 1 2 d S . . C8 C 0.2394(10) 0.2500 0.4306(7) 0.036(2) Uani 1 2 d S . . C9 C 0.3175(7) 0.1662(4) 0.3959(5) 0.0338(16) Uani 1 1 d . . . C10 C 0.2888(7) 0.0823(4) 0.4368(5) 0.0375(17) Uani 1 1 d . . . H10 H 0.2226 0.0777 0.4896 0.045 Uiso 1 1 calc R . . C11 C 0.3557(7) 0.0061(4) 0.4012(5) 0.0363(17) Uani 1 1 d . . . C12 C 0.4480(7) 0.0105(4) 0.3192(5) 0.0399(17) Uani 1 1 d . . . C13 C 0.4779(7) 0.0933(4) 0.2744(5) 0.0389(17) Uani 1 1 d . . . C14 C 0.4124(7) 0.1699(4) 0.3149(5) 0.0347(16) Uani 1 1 d . . . C15 C 0.5726(8) 0.0976(4) 0.1824(5) 0.0503(19) Uani 1 1 d . . . H15A H 0.5090 0.0829 0.1234 0.060 Uiso 1 1 calc R . . H15B H 0.6103 0.1586 0.1743 0.060 Uiso 1 1 calc R . . C16 C 0.7650(8) 0.0177(4) 0.0901(5) 0.052(2) Uani 1 1 d . . . H16A H 0.8094 0.0727 0.0645 0.063 Uiso 1 1 calc R . . H16B H 0.6835 -0.0010 0.0433 0.063 Uiso 1 1 calc R . . C17 C 0.8857(8) -0.0552(5) 0.0974(5) 0.061(2) Uani 1 1 d . . . H17A H 0.9191 -0.0690 0.0303 0.073 Uiso 1 1 calc R . . H17B H 0.8408 -0.1096 0.1243 0.073 Uiso 1 1 calc R . . C18 C 0.9451(8) 0.0047(5) 0.2848(6) 0.068(2) Uani 1 1 d . . . H18A H 0.9014 -0.0494 0.3129 0.082 Uiso 1 1 calc R . . H18B H 1.0160 0.0300 0.3349 0.082 Uiso 1 1 calc R . . C19 C 0.8185(8) 0.0724(4) 0.2617(5) 0.054(2) Uani 1 1 d . . . H19A H 0.7700 0.0887 0.3236 0.065 Uiso 1 1 calc R . . H19B H 0.8619 0.1267 0.2337 0.065 Uiso 1 1 calc R . . O1S O 0.6469(16) 0.2500 0.8321(11) 0.178(5) Uiso 1 2 d SD . . H1S H 0.7022 0.2054 0.8366 0.268 Uiso 0.50 1 calc PR . . C1S C 0.5356(19) 0.2500 0.9193(12) 0.170(7) Uiso 1 2 d SD . . H1S1 H 0.5875 0.2713 0.9795 0.254 Uiso 0.50 1 calc PR . . H1S2 H 0.4991 0.1898 0.9299 0.254 Uiso 0.50 1 calc PR . . H1S3 H 0.4508 0.2890 0.9028 0.254 Uiso 0.50 1 calc PR . . O2S O -0.0345(12) 0.2500 0.0417(9) 0.144(4) Uiso 1 2 d SD . . H2S H -0.0144 0.2440 -0.0177 0.216 Uiso 0.50 1 calc PR . . C2S C 0.1090(15) 0.2500 0.1043(12) 0.160(7) Uiso 1 2 d SD . . H2S1 H 0.1323 0.3105 0.1258 0.241 Uiso 0.50 1 calc PR . . H2S2 H 0.1909 0.2272 0.0655 0.241 Uiso 0.50 1 calc PR . . H2S3 H 0.0968 0.2123 0.1622 0.241 Uiso 0.50 1 calc PR . . 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 0.0657(13) 0.0383(10) 0.0689(14) 0.0064(10) 0.0092(10) -0.0110(9) S1 0.0542(14) 0.0875(17) 0.0938(19) 0.0038(14) 0.0229(13) 0.0122(12) N1 0.042(3) 0.040(3) 0.035(4) -0.010(3) 0.008(3) -0.001(3) O1 0.034(4) 0.055(4) 0.046(4) 0.000 0.003(4) 0.000 O2 0.033(4) 0.048(4) 0.053(5) 0.000 -0.006(4) 0.000 O3 0.049(4) 0.032(4) 0.041(4) 0.000 0.010(3) 0.000 O4 0.057(4) 0.032(3) 0.077(4) -0.006(2) 0.016(3) 0.004(2) C1 0.044(7) 0.028(6) 0.044(7) 0.000 0.000(6) 0.000 C2 0.037(6) 0.037(6) 0.033(6) 0.000 0.004(5) 0.000 C3 0.052(7) 0.032(6) 0.053(8) 0.000 0.007(6) 0.000 C4 0.048(7) 0.046(6) 0.035(7) 0.000 0.000(6) 0.000 C5 0.042(7) 0.046(6) 0.055(8) 0.000 -0.010(6) 0.000 C6 0.037(6) 0.050(6) 0.035(7) 0.000 0.002(6) 0.000 C7 0.030(6) 0.034(5) 0.042(7) 0.000 0.007(5) 0.000 C8 0.025(5) 0.034(6) 0.049(7) 0.000 0.011(5) 0.000 C9 0.022(4) 0.043(4) 0.037(4) 0.002(3) 0.000(3) -0.004(3) C10 0.030(4) 0.046(5) 0.035(4) 0.006(4) -0.001(3) -0.005(3) C11 0.039(4) 0.025(4) 0.045(5) 0.008(3) 0.000(4) -0.003(3) C12 0.037(4) 0.031(4) 0.052(5) -0.004(4) 0.002(4) -0.002(3) C13 0.043(4) 0.037(4) 0.037(4) -0.006(4) 0.008(4) -0.004(3) C14 0.031(4) 0.032(4) 0.041(4) 0.005(4) -0.004(4) 0.001(3) C15 0.053(5) 0.042(4) 0.056(5) -0.004(4) 0.005(4) 0.011(4) C16 0.065(5) 0.045(4) 0.048(5) -0.006(4) 0.014(4) 0.004(4) C17 0.073(6) 0.055(5) 0.057(5) -0.011(4) 0.033(5) -0.002(4) C18 0.049(5) 0.092(6) 0.063(6) -0.006(4) -0.002(4) 0.013(4) C19 0.053(5) 0.057(5) 0.052(5) -0.015(4) 0.007(4) -0.009(4) _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 C11 1.742(6) . ? S1 C17 1.777(7) . ? S1 C18 1.797(7) . ? N1 C15 1.468(7) . ? N1 C16 1.472(8) . ? N1 C19 1.482(7) . ? O1 C1 1.359(11) . ? O1 C8 1.529(10) . ? O2 C1 1.209(10) . ? O3 C14 1.380(7) . ? O3 C14 1.380(7) 4_565 ? O4 C12 1.351(7) . ? O4 H4 0.8200 . ? C1 C2 1.477(12) . ? C2 C7 1.368(11) . ? C2 C3 1.397(12) . ? C3 C4 1.363(12) . ? C3 H3 0.9300 . ? C4 C5 1.423(12) . ? C4 H4A 0.9300 . ? C5 C6 1.351(12) . ? C5 H5 0.9300 . ? C6 C7 1.392(12) . ? C6 H6 0.9300 . ? C7 C8 1.499(12) . ? C8 C9 1.499(8) 4_565 ? C8 C9 1.499(8) . ? C9 C10 1.383(8) . ? C9 C14 1.385(8) . ? C10 C11 1.365(8) . ? C10 H10 0.9300 . ? C11 C12 1.382(9) . ? C12 C13 1.392(8) . ? C13 C14 1.391(8) . ? C13 C15 1.504(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.513(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.519(8) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? O1S C1S 1.54(2) . ? O1S H1S 0.8200 . ? C1S H1S1 0.9600 . ? C1S H1S2 0.9600 . ? C1S H1S3 0.9600 . ? O2S C2S 1.483(18) . ? O2S H2S 0.8300 . ? C2S H2S1 0.9600 . ? C2S H2S2 0.9600 . ? C2S H2S3 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C17 S1 C18 97.1(3) . . ? C15 N1 C16 111.5(5) . . ? C15 N1 C19 108.5(5) . . ? C16 N1 C19 112.1(5) . . ? C1 O1 C8 111.1(7) . . ? C14 O3 C14 118.5(7) . 4_565 ? C12 O4 H4 109.5 . . ? O2 C1 O1 122.9(9) . . ? O2 C1 C2 129.2(10) . . ? O1 C1 C2 107.9(8) . . ? C7 C2 C3 121.7(9) . . ? C7 C2 C1 109.0(9) . . ? C3 C2 C1 129.4(9) . . ? C4 C3 C2 117.7(10) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 119.9(9) . . ? C3 C4 H4A 120.1 . . ? C5 C4 H4A 120.1 . . ? C6 C5 C4 122.1(9) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C7 117.5(9) . . ? C5 C6 H6 121.3 . . ? C7 C6 H6 121.3 . . ? C2 C7 C6 121.1(9) . . ? C2 C7 C8 110.9(8) . . ? C6 C7 C8 127.9(8) . . ? C7 C8 C9 115.2(5) . 4_565 ? C7 C8 C9 115.2(5) . . ? C9 C8 C9 112.0(8) 4_565 . ? C7 C8 O1 101.1(7) . . ? C9 C8 O1 105.9(5) 4_565 . ? C9 C8 O1 105.9(5) . . ? C10 C9 C14 117.7(6) . . ? C10 C9 C8 122.2(6) . . ? C14 C9 C8 119.9(6) . . ? C11 C10 C9 121.4(6) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 120.4(6) . . ? C10 C11 Cl1 119.6(5) . . ? C12 C11 Cl1 120.0(5) . . ? O4 C12 C11 118.5(6) . . ? O4 C12 C13 121.3(7) . . ? C11 C12 C13 120.2(6) . . ? C14 C13 C12 117.9(6) . . ? C14 C13 C15 121.9(6) . . ? C12 C13 C15 120.2(6) . . ? O3 C14 C9 122.4(6) . . ? O3 C14 C13 115.2(6) . . ? C9 C14 C13 122.4(6) . . ? N1 C15 C13 111.7(5) . . ? N1 C15 H15A 109.3 . . ? C13 C15 H15A 109.3 . . ? N1 C15 H15B 109.3 . . ? C13 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? N1 C16 C17 110.5(6) . . ? N1 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? N1 C16 H16B 109.6 . . ? C17 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C16 C17 S1 113.3(5) . . ? C16 C17 H17A 108.9 . . ? S1 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? S1 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C19 C18 S1 112.1(5) . . ? C19 C18 H18A 109.2 . . ? S1 C18 H18A 109.2 . . ? C19 C18 H18B 109.2 . . ? S1 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? N1 C19 C18 111.3(5) . . ? N1 C19 H19A 109.4 . . ? C18 C19 H19A 109.4 . . ? N1 C19 H19B 109.4 . . ? C18 C19 H19B 109.4 . . ? H19A C19 H19B 108.0 . . ? C1S O1S H1S 109.5 . . ? O1S C1S H1S1 109.5 . . ? O1S C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? O1S C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? C2S O2S H2S 110.5 . . ? O2S C2S H2S1 109.5 . . ? O2S C2S H2S2 109.4 . . ? H2S1 C2S H2S2 109.5 . . ? O2S C2S H2S3 109.5 . . ? H2S1 C2S H2S3 109.5 . . ? H2S2 C2S H2S3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O1 C1 O2 180.0 . . . . ? C8 O1 C1 C2 0.000(1) . . . . ? O2 C1 C2 C7 180.000(2) . . . . ? O1 C1 C2 C7 0.000(2) . . . . ? O2 C1 C2 C3 0.000(3) . . . . ? O1 C1 C2 C3 180.000(3) . . . . ? C7 C2 C3 C4 0.000(3) . . . . ? C1 C2 C3 C4 180.000(3) . . . . ? C2 C3 C4 C5 0.000(4) . . . . ? C3 C4 C5 C6 0.000(3) . . . . ? C4 C5 C6 C7 0.000(3) . . . . ? C3 C2 C7 C6 0.000(3) . . . . ? C1 C2 C7 C6 180.000(2) . . . . ? C3 C2 C7 C8 180.000(2) . . . . ? C1 C2 C7 C8 0.000(2) . . . . ? C5 C6 C7 C2 0.000(3) . . . . ? C5 C6 C7 C8 180.000(3) . . . . ? C2 C7 C8 C9 113.6(6) . . . 4_565 ? C6 C7 C8 C9 -66.4(6) . . . 4_565 ? C2 C7 C8 C9 -113.6(6) . . . . ? C6 C7 C8 C9 66.4(6) . . . . ? C2 C7 C8 O1 0.000(2) . . . . ? C6 C7 C8 O1 180.000(2) . . . . ? C1 O1 C8 C7 0.000(2) . . . . ? C1 O1 C8 C9 -120.5(5) . . . 4_565 ? C1 O1 C8 C9 120.5(5) . . . . ? C7 C8 C9 C10 30.7(10) . . . . ? C9 C8 C9 C10 164.9(4) 4_565 . . . ? O1 C8 C9 C10 -80.2(8) . . . . ? C7 C8 C9 C14 -154.8(6) . . . . ? C9 C8 C9 C14 -20.6(10) 4_565 . . . ? O1 C8 C9 C14 94.4(7) . . . . ? C14 C9 C10 C11 2.3(9) . . . . ? C8 C9 C10 C11 177.0(6) . . . . ? C9 C10 C11 C12 -3.5(9) . . . . ? C9 C10 C11 Cl1 180.0(4) . . . . ? C10 C11 C12 O4 -178.6(5) . . . . ? Cl1 C11 C12 O4 -2.1(8) . . . . ? C10 C11 C12 C13 2.2(9) . . . . ? Cl1 C11 C12 C13 178.7(5) . . . . ? O4 C12 C13 C14 -179.0(6) . . . . ? C11 C12 C13 C14 0.2(9) . . . . ? O4 C12 C13 C15 3.6(9) . . . . ? C11 C12 C13 C15 -177.3(6) . . . . ? C14 O3 C14 C9 13.1(10) 4_565 . . . ? C14 O3 C14 C13 -167.5(4) 4_565 . . . ? C10 C9 C14 O3 179.5(5) . . . . ? C8 C9 C14 O3 4.7(9) . . . . ? C10 C9 C14 C13 0.2(9) . . . . ? C8 C9 C14 C13 -174.6(6) . . . . ? C12 C13 C14 O3 179.3(5) . . . . ? C15 C13 C14 O3 -3.3(9) . . . . ? C12 C13 C14 C9 -1.4(9) . . . . ? C15 C13 C14 C9 176.0(6) . . . . ? C16 N1 C15 C13 162.0(5) . . . . ? C19 N1 C15 C13 -74.1(7) . . . . ? C14 C13 C15 N1 142.5(6) . . . . ? C12 C13 C15 N1 -40.2(8) . . . . ? C15 N1 C16 C17 -173.3(6) . . . . ? C19 N1 C16 C17 64.9(7) . . . . ? N1 C16 C17 S1 -63.3(7) . . . . ? C18 S1 C17 C16 53.9(6) . . . . ? C17 S1 C18 C19 -52.8(6) . . . . ? C15 N1 C19 C18 171.4(6) . . . . ? C16 N1 C19 C18 -65.0(7) . . . . ? S1 C18 C19 N1 62.0(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 O4 H4 N1 0.82 1.89 2.625(7) 147.7 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.103 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.071 # Attachment 'CCDC707407(revised).cif' data_SW218 _database_code_depnum_ccdc_archive 'CCDC 707407' _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 Cl2 N2 O8' _chemical_formula_weight 617.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 21.357(2) _cell_length_b 16.3275(15) _cell_length_c 8.9215(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.698(2) _cell_angle_gamma 90.00 _cell_volume 3046.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 669 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 18.28 _exptl_crystal_description rod _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.265 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.991 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details '(SADABS; Bruker, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7842 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2745 _reflns_number_gt 1540 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1112P)^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_number_reflns 2745 _refine_ls_number_parameters 212 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1187 _refine_ls_R_factor_gt 0.0659 _refine_ls_wR_factor_ref 0.1996 _refine_ls_wR_factor_gt 0.1683 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _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 0.11231(5) 0.18246(6) 0.75566(14) 0.0670(4) Uani 1 1 d . . . N1 N -0.12090(14) 0.29168(18) 0.7843(3) 0.0422(8) Uani 1 1 d . . . O1 O 0.13103(19) 0.5000 0.5532(4) 0.0532(10) Uani 1 2 d S . . O2 O 0.2158(3) 0.5000 0.4434(6) 0.1007(18) Uani 1 2 d S . . O3 O -0.01355(16) 0.5000 0.7624(4) 0.0461(9) Uani 1 2 d S . . O4 O -0.01396(13) 0.21156(15) 0.8131(3) 0.0555(8) Uani 1 1 d . . . H4 H -0.0489 0.2217 0.8335 0.083 Uiso 1 1 calc R . . O5 O -0.23280(13) 0.19637(17) 0.6773(3) 0.0572(8) Uani 1 1 d . . . C1 C 0.1962(3) 0.5000 0.5594(9) 0.0637(18) Uani 1 2 d S . . C2 C 0.2286(3) 0.5000 0.7182(9) 0.0619(18) Uani 1 2 d S . . C3 C 0.2935(3) 0.5000 0.7837(13) 0.091(3) Uani 1 2 d S . . H3 H 0.3245 0.5000 0.7240 0.109 Uiso 1 2 calc SR . . C4 C 0.3100(4) 0.5000 0.9448(16) 0.106(3) Uani 1 2 d S . . H4A H 0.3531 0.5000 0.9919 0.127 Uiso 1 2 calc SR . . C5 C 0.2658(4) 0.5000 1.0334(10) 0.082(2) Uani 1 2 d S . . H5 H 0.2787 0.5000 1.1394 0.099 Uiso 1 2 calc SR . . C6 C 0.2016(3) 0.5000 0.9680(8) 0.0609(16) Uani 1 2 d S . . H6 H 0.1712 0.5000 1.0292 0.073 Uiso 1 2 calc SR . . C7 C 0.1829(3) 0.5000 0.8111(7) 0.0502(14) Uani 1 2 d S . . C8 C 0.1174(2) 0.5000 0.7106(6) 0.0405(12) Uani 1 2 d S . . C9 C 0.08055(18) 0.4240(2) 0.7295(4) 0.0417(9) Uani 1 1 d . . . C10 C 0.10792(18) 0.3468(2) 0.7276(4) 0.0435(9) Uani 1 1 d . . . H10 H 0.1490 0.3422 0.7086 0.052 Uiso 1 1 calc R . . C11 C 0.07562(19) 0.2776(2) 0.7533(4) 0.0460(10) Uani 1 1 d . . . C12 C 0.01365(18) 0.2811(2) 0.7824(4) 0.0428(9) Uani 1 1 d . . . C13 C -0.01704(17) 0.3574(2) 0.7776(4) 0.0418(9) Uani 1 1 d . . . C14 C 0.01790(18) 0.4272(2) 0.7534(4) 0.0407(9) Uani 1 1 d . . . C15 C -0.08272(17) 0.3678(2) 0.8091(4) 0.0459(9) Uani 1 1 d . . . H15A H -0.0793 0.3855 0.9143 0.055 Uiso 1 1 calc R . . H15B H -0.1048 0.4104 0.7431 0.055 Uiso 1 1 calc R . . C16 C -0.14366(19) 0.2739(2) 0.6207(4) 0.0480(10) Uani 1 1 d . . . H16A H -0.1076 0.2704 0.5701 0.058 Uiso 1 1 calc R . . H16B H -0.1715 0.3175 0.5731 0.058 Uiso 1 1 calc R . . C17 C -0.1795(2) 0.1940(3) 0.6041(5) 0.0581(11) Uani 1 1 d . . . H17A H -0.1943 0.1819 0.4962 0.070 Uiso 1 1 calc R . . H17B H -0.1508 0.1503 0.6485 0.070 Uiso 1 1 calc R . . C18 C -0.2124(2) 0.2157(3) 0.8335(5) 0.0573(11) Uani 1 1 d . . . H18A H -0.1848 0.1724 0.8837 0.069 Uiso 1 1 calc R . . H18B H -0.2493 0.2189 0.8812 0.069 Uiso 1 1 calc R . . C19 C -0.1767(2) 0.2959(3) 0.8557(5) 0.0524(10) Uani 1 1 d . . . H19A H -0.2047 0.3399 0.8099 0.063 Uiso 1 1 calc R . . H19B H -0.1631 0.3072 0.9641 0.063 Uiso 1 1 calc R . . O1S O 0.4482(14) 0.5000 0.579(3) 0.100(3) Uiso 1 2 d SD . . H1SA H 0.4199(13) 0.5000 0.495(3) 0.065(8) Uiso 1 2 d SD . . H1SB H 0.456(3) 0.5000 0.677(3) 0.060(16) Uiso 1 2 d SD . . 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 0.0667(8) 0.0386(6) 0.0999(9) 0.0009(5) 0.0263(6) 0.0105(5) N1 0.0442(18) 0.0391(17) 0.0448(18) -0.0052(13) 0.0125(15) -0.0071(14) O1 0.058(3) 0.053(2) 0.052(2) 0.000 0.020(2) 0.000 O2 0.115(4) 0.084(4) 0.129(4) 0.000 0.087(4) 0.000 O3 0.040(2) 0.031(2) 0.069(2) 0.000 0.0152(19) 0.000 O4 0.0554(18) 0.0328(15) 0.080(2) 0.0061(13) 0.0183(16) -0.0024(13) O5 0.0519(17) 0.0646(19) 0.0571(18) -0.0120(13) 0.0157(15) -0.0196(14) C1 0.072(5) 0.044(4) 0.091(5) 0.000 0.053(4) 0.000 C2 0.044(4) 0.032(3) 0.116(6) 0.000 0.032(4) 0.000 C3 0.042(4) 0.042(4) 0.194(10) 0.000 0.038(5) 0.000 C4 0.044(5) 0.053(5) 0.199(11) 0.000 -0.024(7) 0.000 C5 0.062(5) 0.051(4) 0.111(6) 0.000 -0.035(5) 0.000 C6 0.060(4) 0.036(3) 0.079(5) 0.000 -0.004(3) 0.000 C7 0.046(3) 0.030(3) 0.074(4) 0.000 0.012(3) 0.000 C8 0.039(3) 0.036(3) 0.049(3) 0.000 0.016(3) 0.000 C9 0.042(2) 0.039(2) 0.043(2) -0.0040(16) 0.0061(17) -0.0024(17) C10 0.044(2) 0.036(2) 0.052(2) -0.0031(16) 0.0133(18) 0.0015(18) C11 0.049(2) 0.036(2) 0.052(2) -0.0007(17) 0.0055(19) 0.0035(18) C12 0.046(2) 0.035(2) 0.047(2) 0.0001(16) 0.0073(18) -0.0026(18) C13 0.042(2) 0.037(2) 0.047(2) -0.0026(16) 0.0089(18) -0.0046(17) C14 0.043(2) 0.034(2) 0.044(2) -0.0025(15) 0.0048(17) 0.0007(17) C15 0.045(2) 0.038(2) 0.056(2) -0.0005(17) 0.0139(19) -0.0035(18) C16 0.051(2) 0.049(2) 0.046(2) 0.0024(17) 0.014(2) -0.0057(19) C17 0.064(3) 0.060(3) 0.050(2) -0.0111(19) 0.010(2) -0.010(2) C18 0.053(3) 0.061(3) 0.063(3) -0.003(2) 0.023(2) -0.012(2) C19 0.052(2) 0.054(3) 0.053(2) -0.0072(18) 0.016(2) -0.010(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 C11 1.738(4) . ? N1 C19 1.462(5) . ? N1 C16 1.471(4) . ? N1 C15 1.478(4) . ? O1 C1 1.381(8) . ? O1 C8 1.491(6) . ? O2 C1 1.193(7) . ? O3 C14 1.376(4) 6_565 ? O3 C14 1.376(4) . ? O4 C12 1.334(4) . ? O4 H4 0.8200 . ? O5 C18 1.410(4) . ? O5 C17 1.423(5) . ? C1 C2 1.445(9) . ? C2 C3 1.390(10) . ? C2 C7 1.403(8) . ? C3 C4 1.409(12) . ? C3 H3 0.9300 . ? C4 C5 1.349(12) . ? C4 H4A 0.9300 . ? C5 C6 1.377(10) . ? C5 H5 0.9300 . ? C6 C7 1.375(8) . ? C6 H6 0.9300 . ? C7 C8 1.501(8) . ? C8 C9 1.497(4) . ? C8 C9 1.497(4) 6_565 ? C9 C10 1.390(5) . ? C9 C14 1.398(5) . ? C10 C11 1.368(5) . ? C10 H10 0.9300 . ? C11 C12 1.401(6) . ? C12 C13 1.404(5) . ? C13 C14 1.402(5) . ? C13 C15 1.495(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.505(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.507(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? O1S H1SA 0.86(4) . ? O1S H1SB 0.86(4) . ? 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 C19 N1 C16 107.8(3) . . ? C19 N1 C15 111.7(3) . . ? C16 N1 C15 112.1(3) . . ? C1 O1 C8 110.5(4) . . ? C14 O3 C14 119.6(4) 6_565 . ? C12 O4 H4 109.5 . . ? C18 O5 C17 110.1(3) . . ? O2 C1 O1 119.6(7) . . ? O2 C1 C2 131.9(7) . . ? O1 C1 C2 108.5(5) . . ? C3 C2 C7 120.4(7) . . ? C3 C2 C1 130.6(7) . . ? C7 C2 C1 109.0(5) . . ? C2 C3 C4 116.8(8) . . ? C2 C3 H3 121.6 . . ? C4 C3 H3 121.6 . . ? C5 C4 C3 122.5(7) . . ? C5 C4 H4A 118.8 . . ? C3 C4 H4A 118.8 . . ? C4 C5 C6 120.5(8) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 119.4(7) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 120.5(6) . . ? C6 C7 C8 130.7(5) . . ? C2 C7 C8 108.9(5) . . ? O1 C8 C9 108.3(3) . . ? O1 C8 C9 108.3(3) . 6_565 ? C9 C8 C9 112.0(4) . 6_565 ? O1 C8 C7 103.0(4) . . ? C9 C8 C7 112.3(3) . . ? C9 C8 C7 112.3(3) 6_565 . ? C10 C9 C14 117.0(3) . . ? C10 C9 C8 121.2(3) . . ? C14 C9 C8 121.8(3) . . ? C11 C10 C9 121.3(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 121.6(3) . . ? C10 C11 Cl1 120.0(3) . . ? C12 C11 Cl1 118.4(3) . . ? O4 C12 C11 118.4(3) . . ? O4 C12 C13 122.6(3) . . ? C11 C12 C13 118.9(3) . . ? C14 C13 C12 117.8(3) . . ? C14 C13 C15 119.1(3) . . ? C12 C13 C15 123.0(3) . . ? O3 C14 C9 122.4(3) . . ? O3 C14 C13 114.3(3) . . ? C9 C14 C13 123.3(3) . . ? N1 C15 C13 112.8(3) . . ? N1 C15 H15A 109.0 . . ? C13 C15 H15A 109.0 . . ? N1 C15 H15B 109.0 . . ? C13 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? N1 C16 C17 109.2(3) . . ? N1 C16 H16A 109.8 . . ? C17 C16 H16A 109.8 . . ? N1 C16 H16B 109.8 . . ? C17 C16 H16B 109.8 . . ? H16A C16 H16B 108.3 . . ? O5 C17 C16 111.6(3) . . ? O5 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? O5 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? O5 C18 C19 111.8(3) . . ? O5 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? O5 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? N1 C19 C18 109.7(3) . . ? N1 C19 H19A 109.7 . . ? C18 C19 H19A 109.7 . . ? N1 C19 H19B 109.7 . . ? C18 C19 H19B 109.7 . . ? H19A C19 H19B 108.2 . . ? H1SA O1S H1SB 147(7) . . ? 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 C8 O1 C1 O2 180.0 . . . . ? C8 O1 C1 C2 0.000(1) . . . . ? O2 C1 C2 C3 0.000(3) . . . . ? O1 C1 C2 C3 180.000(2) . . . . ? O2 C1 C2 C7 180.000(1) . . . . ? O1 C1 C2 C7 0.000(1) . . . . ? C7 C2 C3 C4 0.000(3) . . . . ? C1 C2 C3 C4 180.000(4) . . . . ? C2 C3 C4 C5 0.000(3) . . . . ? C3 C4 C5 C6 0.000(3) . . . . ? C4 C5 C6 C7 0.000(2) . . . . ? C5 C6 C7 C2 0.000(2) . . . . ? C5 C6 C7 C8 180.000(2) . . . . ? C3 C2 C7 C6 0.000(3) . . . . ? C1 C2 C7 C6 180.000(2) . . . . ? C3 C2 C7 C8 180.000(2) . . . . ? C1 C2 C7 C8 0.000(1) . . . . ? C1 O1 C8 C9 -119.1(3) . . . . ? C1 O1 C8 C9 119.2(3) . . . 6_565 ? C1 O1 C8 C7 0.000(1) . . . . ? C6 C7 C8 O1 180.000(2) . . . . ? C2 C7 C8 O1 0.000(1) . . . . ? C6 C7 C8 C9 -63.7(3) . . . . ? C2 C7 C8 C9 116.3(3) . . . . ? C6 C7 C8 C9 63.7(3) . . . 6_565 ? C2 C7 C8 C9 -116.3(3) . . . 6_565 ? O1 C8 C9 C10 65.5(5) . . . . ? C9 C8 C9 C10 -175.2(2) 6_565 . . . ? C7 C8 C9 C10 -47.6(5) . . . . ? O1 C8 C9 C14 -116.1(4) . . . . ? C9 C8 C9 C14 3.3(6) 6_565 . . . ? C7 C8 C9 C14 130.8(4) . . . . ? C14 C9 C10 C11 -2.2(5) . . . . ? C8 C9 C10 C11 176.4(4) . . . . ? C9 C10 C11 C12 0.0(6) . . . . ? C9 C10 C11 Cl1 -178.1(3) . . . . ? C10 C11 C12 O4 -177.1(3) . . . . ? Cl1 C11 C12 O4 1.0(5) . . . . ? C10 C11 C12 C13 3.2(6) . . . . ? Cl1 C11 C12 C13 -178.7(3) . . . . ? O4 C12 C13 C14 176.3(3) . . . . ? C11 C12 C13 C14 -4.1(5) . . . . ? O4 C12 C13 C15 1.2(6) . . . . ? C11 C12 C13 C15 -179.1(3) . . . . ? C14 O3 C14 C9 -2.4(6) 6_565 . . . ? C14 O3 C14 C13 174.6(2) 6_565 . . . ? C10 C9 C14 O3 177.9(3) . . . . ? C8 C9 C14 O3 -0.6(6) . . . . ? C10 C9 C14 C13 1.2(5) . . . . ? C8 C9 C14 C13 -177.4(4) . . . . ? C12 C13 C14 O3 -175.0(3) . . . . ? C15 C13 C14 O3 0.3(5) . . . . ? C12 C13 C14 C9 2.0(5) . . . . ? C15 C13 C14 C9 177.2(3) . . . . ? C19 N1 C15 C13 163.8(3) . . . . ? C16 N1 C15 C13 -75.0(4) . . . . ? C14 C13 C15 N1 162.0(3) . . . . ? C12 C13 C15 N1 -23.0(5) . . . . ? C19 N1 C16 C17 -59.2(4) . . . . ? C15 N1 C16 C17 177.5(3) . . . . ? C18 O5 C17 C16 -57.6(4) . . . . ? N1 C16 C17 O5 59.4(4) . . . . ? C17 O5 C18 C19 57.1(4) . . . . ? C16 N1 C19 C18 59.0(4) . . . . ? C15 N1 C19 C18 -177.4(3) . . . . ? O5 C18 C19 N1 -59.0(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 O4 H4 N1 0.82 1.89 2.599(4) 143.4 . _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.933 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.078