# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Madeleine Helliwell' _publ_contact_author_email madeleine.helliwell@manchester.ac.uk _publ_author_name E.Thomas data_s319b _database_code_depnum_ccdc_archive 'CCDC 862199' #TrackingRef 's319b.cif' _chemical_name_systematic ; ? ; #------------------------------------------------------------------------------ _audit_creation_date 19100-11-21 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Sheldrick, G.M. (1985). In: "Crystallographic Computing 3" (Eds G.M. Sheldrick, C. Kruger and R. Goddard) Oxford University Press, pp. 175-189. DIFABS - Walker, N. and Stuart, D. (1983) Acta Cryst. A39, 158-166. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 Cl3 N O4' _chemical_formula_sum 'C22 H30 Cl3 N O4' _chemical_formula_weight 478.82 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.185(5) _cell_length_b 11.218(10) _cell_length_c 10.307(5) _cell_angle_alpha 104.76(5) _cell_angle_beta 91.60(4) _cell_angle_gamma 100.21(5) _cell_volume 1227.2(14) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25 _cell_measurement_theta_max 40 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 3.603 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 1.08 _exptl_absorpt_process_details DIFABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC5R _diffrn_measurement_method '2theta-omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 40.0 _diffrn_reflns_number 3630 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 60.07 _reflns_number_total 3630 _reflns_number_gt 2627 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1253P)^2^+0.6941P] 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 3630 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1010 _refine_ls_R_factor_gt 0.0725 _refine_ls_wR_factor_ref 0.2327 _refine_ls_wR_factor_gt 0.2040 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 0.32128(13) 0.12322(14) 0.48107(14) 0.1032(5) Uani 1 1 d . . . Cl2 Cl 0.38010(14) 0.35781(12) 0.41539(14) 0.1004(5) Uani 1 1 d . . . Cl3 Cl 0.56065(14) 0.27210(18) 0.54808(14) 0.1149(6) Uani 1 1 d . . . O1 O 0.6189(3) 0.1425(3) 0.0636(3) 0.0938(11) Uani 1 1 d . . . O2 O 0.5689(3) 0.2540(3) 0.2649(3) 0.0737(8) Uani 1 1 d . . . O3 O 0.8673(3) 0.1637(3) -0.0811(4) 0.1024(12) Uani 1 1 d . . . O4 O 0.8996(3) 0.2295(3) 0.1433(4) 0.0935(10) Uani 1 1 d . . . N1 N 0.7045(3) 0.3470(3) 0.1516(3) 0.0688(9) Uani 1 1 d . . . C1 C 0.7209(4) 0.4617(4) 0.2637(4) 0.0706(11) Uani 1 1 d . . . H1 H 0.6464 0.4558 0.3114 0.085 Uiso 1 1 calc R . . C2 C 0.7854(4) 0.3415(4) 0.0420(4) 0.0733(12) Uani 1 1 d . . . H2 H 0.8480 0.4181 0.0691 0.088 Uiso 1 1 calc R . . C3 C 0.8524(4) 0.2327(5) 0.0231(5) 0.0851(14) Uani 1 1 d . . . C4 C 0.9673(7) 0.1304(6) 0.1427(7) 0.115(2) Uani 1 1 d . . . H4A H 1.0376 0.1390 0.0906 0.138 Uiso 1 1 calc R . . H4B H 0.9162 0.0487 0.1041 0.138 Uiso 1 1 calc R . . C5 C 1.0068(6) 0.1449(7) 0.2881(9) 0.127(2) Uani 1 1 d . . . H5A H 1.0513 0.2297 0.3273 0.153 Uiso 1 1 calc R . . H5B H 1.0611 0.0874 0.2925 0.153 Uiso 1 1 calc R . . C6 C 0.8957(7) 0.1179(7) 0.3709(7) 0.120(2) Uani 1 1 d . . . H6A H 0.8341 0.1633 0.3520 0.144 Uiso 1 1 calc R . . H6B H 0.8607 0.0289 0.3427 0.144 Uiso 1 1 calc R . . C7 C 0.9287(10) 0.1541(9) 0.5143(9) 0.184(4) Uani 1 1 d . . . H7A H 0.9843 0.1041 0.5345 0.276 Uiso 1 1 calc R . . H7B H 0.8568 0.1411 0.5615 0.276 Uiso 1 1 calc R . . H7C H 0.9669 0.2412 0.5420 0.276 Uiso 1 1 calc R . . C8 C 0.7212(5) 0.3444(6) -0.0908(5) 0.0907(15) Uani 1 1 d . . . H8A H 0.6769 0.2606 -0.1350 0.109 Uiso 1 1 calc R . . H8B H 0.6622 0.3991 -0.0704 0.109 Uiso 1 1 calc R . . C9 C 0.8051(6) 0.3884(8) -0.1858(6) 0.111(2) Uani 1 1 d . . . H9 H 0.8523 0.3327 -0.2303 0.134 Uiso 1 1 calc R . . C10 C 0.8183(8) 0.4924(10) -0.2117(8) 0.155(3) Uani 1 1 d . . . H10A H 0.7731 0.5514 -0.1697 0.186 Uiso 1 1 calc R . . H10B H 0.8734 0.5111 -0.2729 0.186 Uiso 1 1 calc R . . C11 C 0.7286(4) 0.5772(4) 0.2109(4) 0.0672(11) Uani 1 1 d . . . C12 C 0.8365(4) 0.6570(4) 0.2104(5) 0.0751(12) Uani 1 1 d . . . H12 H 0.9084 0.6400 0.2425 0.090 Uiso 1 1 calc R . . C13 C 0.8403(5) 0.7627(5) 0.1629(5) 0.0849(14) Uani 1 1 d . . . H13 H 0.9143 0.8156 0.1622 0.102 Uiso 1 1 calc R . . C14 C 0.7354(5) 0.7879(5) 0.1176(6) 0.0921(15) Uani 1 1 d . . . H14 H 0.7374 0.8601 0.0883 0.110 Uiso 1 1 calc R . . C15 C 0.6272(5) 0.7096(5) 0.1142(6) 0.0953(15) Uani 1 1 d . . . H15 H 0.5560 0.7268 0.0804 0.114 Uiso 1 1 calc R . . C16 C 0.6235(4) 0.6050(5) 0.1610(5) 0.0820(13) Uani 1 1 d . . . H16 H 0.5492 0.5517 0.1591 0.098 Uiso 1 1 calc R . . C17 C 0.8244(5) 0.4677(5) 0.3649(5) 0.0858(14) Uani 1 1 d . . . H17A H 0.8065 0.3975 0.4031 0.129 Uiso 1 1 calc R . . H17B H 0.8337 0.5444 0.4350 0.129 Uiso 1 1 calc R . . H17C H 0.8986 0.4648 0.3205 0.129 Uiso 1 1 calc R . . C18 C 0.6292(4) 0.2386(4) 0.1516(4) 0.0729(12) Uani 1 1 d . . . C19 C 0.4762(4) 0.1550(4) 0.2864(4) 0.0701(11) Uani 1 1 d . . . C20 C 0.3707(5) 0.1194(5) 0.1785(5) 0.0859(14) Uani 1 1 d . . . H20A H 0.3415 0.1935 0.1728 0.129 Uiso 1 1 calc R . . H20B H 0.3060 0.0616 0.2015 0.129 Uiso 1 1 calc R . . H20C H 0.3981 0.0807 0.0933 0.129 Uiso 1 1 calc R . . C21 C 0.5287(5) 0.0408(5) 0.2944(7) 0.1018(17) Uani 1 1 d . . . H21A H 0.5540 0.0024 0.2080 0.153 Uiso 1 1 calc R . . H21B H 0.4677 -0.0183 0.3208 0.153 Uiso 1 1 calc R . . H21C H 0.5975 0.0664 0.3596 0.153 Uiso 1 1 calc R . . C22 C 0.4369(4) 0.2233(4) 0.4252(5) 0.0759(12) 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 Cl1 0.0941(9) 0.1189(11) 0.1032(10) 0.0477(8) 0.0299(7) 0.0071(8) Cl2 0.1198(11) 0.0828(8) 0.1013(10) 0.0137(7) 0.0364(8) 0.0379(7) Cl3 0.0981(10) 0.1622(15) 0.0745(8) 0.0288(8) 0.0008(7) 0.0034(9) O1 0.101(2) 0.072(2) 0.084(2) -0.0124(17) 0.0348(18) -0.0023(17) O2 0.0810(19) 0.0603(16) 0.0714(18) 0.0075(13) 0.0252(15) 0.0028(14) O3 0.100(3) 0.100(3) 0.089(2) -0.013(2) 0.033(2) 0.023(2) O4 0.112(3) 0.081(2) 0.090(2) 0.0107(18) 0.024(2) 0.0387(19) N1 0.072(2) 0.065(2) 0.0608(19) 0.0020(16) 0.0182(16) 0.0086(17) C1 0.080(3) 0.058(2) 0.068(3) 0.0070(19) 0.017(2) 0.009(2) C2 0.070(3) 0.078(3) 0.064(2) 0.006(2) 0.021(2) 0.010(2) C3 0.077(3) 0.082(3) 0.083(3) 0.001(3) 0.024(3) 0.007(2) C4 0.132(5) 0.106(4) 0.123(5) 0.028(4) 0.040(4) 0.062(4) C5 0.106(5) 0.115(5) 0.182(8) 0.060(5) 0.014(5) 0.044(4) C6 0.124(5) 0.110(5) 0.123(5) 0.021(4) 0.003(4) 0.030(4) C7 0.247(12) 0.157(8) 0.128(7) 0.011(6) -0.018(7) 0.030(8) C8 0.080(3) 0.114(4) 0.071(3) 0.016(3) 0.013(2) 0.012(3) C9 0.096(4) 0.160(6) 0.079(3) 0.035(4) 0.020(3) 0.020(4) C10 0.136(6) 0.208(9) 0.153(7) 0.104(7) 0.048(5) 0.029(6) C11 0.066(3) 0.065(2) 0.063(2) 0.0061(19) 0.0124(19) 0.008(2) C12 0.064(3) 0.074(3) 0.086(3) 0.020(2) 0.008(2) 0.011(2) C13 0.072(3) 0.081(3) 0.097(3) 0.024(3) 0.008(3) 0.001(2) C14 0.099(4) 0.083(3) 0.095(4) 0.031(3) 0.008(3) 0.010(3) C15 0.083(3) 0.091(4) 0.112(4) 0.030(3) -0.006(3) 0.016(3) C16 0.060(3) 0.079(3) 0.102(4) 0.020(3) 0.006(2) 0.006(2) C17 0.105(4) 0.074(3) 0.071(3) 0.008(2) -0.003(3) 0.015(3) C18 0.074(3) 0.070(3) 0.066(3) 0.005(2) 0.021(2) 0.006(2) C19 0.070(3) 0.061(2) 0.073(3) 0.010(2) 0.013(2) 0.007(2) C20 0.087(3) 0.085(3) 0.077(3) 0.009(2) 0.011(2) 0.009(3) C21 0.102(4) 0.077(3) 0.138(5) 0.035(3) 0.028(4) 0.033(3) C22 0.078(3) 0.075(3) 0.073(3) 0.015(2) 0.013(2) 0.012(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 C22 1.766(5) . ? Cl2 C22 1.762(5) . ? Cl3 C22 1.761(5) . ? O1 C18 1.204(5) . ? O2 C18 1.353(5) . ? O2 C19 1.445(5) . ? O3 C3 1.189(5) . ? O4 C3 1.345(6) . ? O4 C4 1.450(7) . ? N1 C18 1.351(5) . ? N1 C2 1.463(5) . ? N1 C1 1.474(5) . ? C1 C17 1.517(7) . ? C1 C11 1.518(6) . ? C1 H1 0.9800 . ? C2 C3 1.516(7) . ? C2 C8 1.539(7) . ? C2 H2 0.9800 . ? C4 C5 1.510(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.555(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.448(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.488(8) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.247(10) . ? C9 H9 0.9300 . ? C10 H10A 0.9300 . ? C10 H10B 0.9300 . ? C11 C12 1.370(6) . ? C11 C16 1.387(7) . ? C12 C13 1.388(7) . ? C12 H12 0.9300 . ? C13 C14 1.353(7) . ? C13 H13 0.9300 . ? C14 C15 1.357(7) . ? C14 H14 0.9300 . ? C15 C16 1.373(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C19 C21 1.519(6) . ? C19 C20 1.524(6) . ? C19 C22 1.556(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 C18 O2 C19 121.6(3) . . ? C3 O4 C4 116.4(4) . . ? C18 N1 C2 116.3(3) . . ? C18 N1 C1 123.6(3) . . ? C2 N1 C1 119.4(3) . . ? N1 C1 C17 111.9(4) . . ? N1 C1 C11 110.6(3) . . ? C17 C1 C11 114.8(4) . . ? N1 C1 H1 106.3 . . ? C17 C1 H1 106.3 . . ? C11 C1 H1 106.3 . . ? N1 C2 C3 112.6(4) . . ? N1 C2 C8 113.0(4) . . ? C3 C2 C8 111.9(4) . . ? N1 C2 H2 106.2 . . ? C3 C2 H2 106.2 . . ? C8 C2 H2 106.2 . . ? O3 C3 O4 124.2(5) . . ? O3 C3 C2 126.3(5) . . ? O4 C3 C2 109.4(4) . . ? O4 C4 C5 106.0(5) . . ? O4 C4 H4A 110.5 . . ? C5 C4 H4A 110.5 . . ? O4 C4 H4B 110.5 . . ? C5 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? C4 C5 C6 111.5(6) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 112.4(7) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C2 114.2(4) . . ? C9 C8 H8A 108.7 . . ? C2 C8 H8A 108.7 . . ? C9 C8 H8B 108.7 . . ? C2 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C10 C9 C8 126.6(7) . . ? C10 C9 H9 116.7 . . ? C8 C9 H9 116.7 . . ? C9 C10 H10A 120.0 . . ? C9 C10 H10B 120.0 . . ? H10A C10 H10B 120.0 . . ? C12 C11 C16 117.6(4) . . ? C12 C11 C1 122.6(4) . . ? C16 C11 C1 119.7(4) . . ? C11 C12 C13 121.2(5) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 119.3(5) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 121.0(5) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C14 C15 C16 119.6(5) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C11 121.2(4) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? C1 C17 H17A 109.5 . . ? C1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 N1 124.5(4) . . ? O1 C18 O2 125.5(4) . . ? N1 C18 O2 110.1(3) . . ? O2 C19 C21 111.5(4) . . ? O2 C19 C20 111.3(4) . . ? C21 C19 C20 111.1(4) . . ? O2 C19 C22 99.8(3) . . ? C21 C19 C22 111.7(4) . . ? C20 C19 C22 111.1(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 Cl2 111.1(3) . . ? C19 C22 Cl3 111.2(3) . . ? Cl2 C22 Cl3 107.5(2) . . ? C19 C22 Cl1 110.8(3) . . ? Cl2 C22 Cl1 107.9(2) . . ? Cl3 C22 Cl1 108.1(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 C18 N1 C1 C17 91.0(5) . . . . ? C2 N1 C1 C17 -79.7(5) . . . . ? C18 N1 C1 C11 -139.6(4) . . . . ? C2 N1 C1 C11 49.7(5) . . . . ? C18 N1 C2 C3 -48.8(5) . . . . ? C1 N1 C2 C3 122.5(4) . . . . ? C18 N1 C2 C8 79.3(5) . . . . ? C1 N1 C2 C8 -109.4(5) . . . . ? C4 O4 C3 O3 -3.2(7) . . . . ? C4 O4 C3 C2 -179.8(4) . . . . ? N1 C2 C3 O3 136.3(5) . . . . ? C8 C2 C3 O3 7.7(7) . . . . ? N1 C2 C3 O4 -47.2(5) . . . . ? C8 C2 C3 O4 -175.8(4) . . . . ? C3 O4 C4 C5 -178.3(5) . . . . ? O4 C4 C5 C6 66.1(7) . . . . ? C4 C5 C6 C7 -168.9(6) . . . . ? N1 C2 C8 C9 157.3(5) . . . . ? C3 C2 C8 C9 -74.3(6) . . . . ? C2 C8 C9 C10 -106.0(9) . . . . ? N1 C1 C11 C12 -103.8(5) . . . . ? C17 C1 C11 C12 24.0(6) . . . . ? N1 C1 C11 C16 76.3(5) . . . . ? C17 C1 C11 C16 -155.8(4) . . . . ? C16 C11 C12 C13 0.7(7) . . . . ? C1 C11 C12 C13 -179.2(4) . . . . ? C11 C12 C13 C14 0.7(8) . . . . ? C12 C13 C14 C15 -2.0(8) . . . . ? C13 C14 C15 C16 1.9(9) . . . . ? C14 C15 C16 C11 -0.4(8) . . . . ? C12 C11 C16 C15 -0.8(7) . . . . ? C1 C11 C16 C15 179.1(4) . . . . ? C2 N1 C18 O1 -5.5(7) . . . . ? C1 N1 C18 O1 -176.4(5) . . . . ? C2 N1 C18 O2 173.8(4) . . . . ? C1 N1 C18 O2 2.8(6) . . . . ? C19 O2 C18 O1 -5.1(8) . . . . ? C19 O2 C18 N1 175.7(4) . . . . ? C18 O2 C19 C21 63.5(6) . . . . ? C18 O2 C19 C20 -61.1(5) . . . . ? C18 O2 C19 C22 -178.4(4) . . . . ? O2 C19 C22 Cl2 60.4(4) . . . . ? C21 C19 C22 Cl2 178.4(3) . . . . ? C20 C19 C22 Cl2 -57.0(4) . . . . ? O2 C19 C22 Cl3 -59.4(4) . . . . ? C21 C19 C22 Cl3 58.6(5) . . . . ? C20 C19 C22 Cl3 -176.8(3) . . . . ? O2 C19 C22 Cl1 -179.7(3) . . . . ? C21 C19 C22 Cl1 -61.7(5) . . . . ? C20 C19 C22 Cl1 62.9(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 60.07 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.378 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.064 # Attachment 's351b.cif' data_s351b _database_code_depnum_ccdc_archive 'CCDC 862200' #TrackingRef 's351b.cif' #_audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; #------------------------------------------------------------------------------ _audit_creation_date 19100-11-21 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; ENTER EXPERIMENTAL SECTION ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Sheldrick, G.M. (1985). In: "Crystallographic Computing 3" (Eds G.M. Sheldrick, C. Kruger and R. Goddard) Oxford University Press, pp. 175-189. DIFABS - Walker, N. and Stuart, D. (1983) Acta Cryst. A39, 158-166. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H21 N O4' _chemical_formula_sum 'C20 H21 N O4' _chemical_formula_weight 339.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.681(3) _cell_length_b 28.33(1) _cell_length_c 6.260(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1716.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 4 _cell_measurement_theta_max 60 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.746 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7827 _exptl_absorpt_correction_T_max 1.1686 _exptl_absorpt_process_details DIFABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type AFC5R _diffrn_measurement_method '2theta-omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1.5 _diffrn_reflns_number 1503 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 60.01 _reflns_number_total 1503 _reflns_number_gt 1045 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0000P)^2^+4.5630P] 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 ? _chemical_absolute_configuration syn _refine_ls_number_reflns 1503 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1436 _refine_ls_R_factor_gt 0.0735 _refine_ls_wR_factor_ref 0.1915 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.201 _refine_ls_restrained_S_all 1.201 _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 0.1612(7) 0.7792(2) 0.5879(13) 0.072(2) Uani 1 1 d . . . O2 O 0.1786(8) 0.7057(3) 0.6972(12) 0.078(2) Uani 1 1 d . . . O3 O 0.3127(6) 0.7043(2) 0.2643(11) 0.0593(17) Uani 1 1 d . . . O4 O 0.2519(6) 0.6336(2) 0.1209(11) 0.0550(17) Uani 1 1 d . . . N1 N 0.0887(7) 0.6804(2) 0.2611(12) 0.0462(17) Uani 1 1 d . . . C1 C 0.0489(9) 0.7239(3) 0.3737(15) 0.047(2) Uani 1 1 d . . . H1 H -0.0465 0.7197 0.4225 0.057 Uiso 1 1 calc R . . C2 C 0.1371(10) 0.7333(4) 0.5709(18) 0.062(3) Uani 1 1 d . . . C3 C 0.0933(12) 0.8051(3) 0.4176(19) 0.075(3) Uani 1 1 d . . . H3A H 0.1552 0.8286 0.3584 0.090 Uiso 1 1 calc R . . H3B H 0.0116 0.8209 0.4714 0.090 Uiso 1 1 calc R . . C4 C 0.0538(10) 0.7691(3) 0.247(2) 0.067(3) Uani 1 1 d . . . H4A H -0.0354 0.7764 0.1846 0.080 Uiso 1 1 calc R . . H4B H 0.1227 0.7676 0.1348 0.080 Uiso 1 1 calc R . . C5 C 0.2250(9) 0.6751(3) 0.2168(16) 0.051(2) Uani 1 1 d . . . C6 C 0.3944(9) 0.6264(3) 0.0576(18) 0.065(3) Uani 1 1 d . . . H6A H 0.4503 0.6177 0.1799 0.078 Uiso 1 1 calc R . . H6B H 0.4321 0.6550 -0.0047 0.078 Uiso 1 1 calc R . . C7 C 0.3922(9) 0.5870(3) -0.1052(15) 0.049(2) Uani 1 1 d . . . C8 C 0.3294(10) 0.5938(3) -0.3015(16) 0.060(3) Uani 1 1 d . . . H8 H 0.2906 0.6229 -0.3347 0.072 Uiso 1 1 calc R . . C9 C 0.3242(11) 0.5573(3) -0.4485(19) 0.070(3) Uani 1 1 d . . . H9 H 0.2830 0.5623 -0.5808 0.084 Uiso 1 1 calc R . . C10 C 0.3782(11) 0.5146(4) -0.4020(18) 0.068(3) Uani 1 1 d . . . H10 H 0.3706 0.4899 -0.4992 0.082 Uiso 1 1 calc R . . C11 C 0.4444(10) 0.5078(3) -0.2109(19) 0.068(3) Uani 1 1 d . . . H11 H 0.4854 0.4789 -0.1807 0.082 Uiso 1 1 calc R . . C12 C 0.4499(9) 0.5437(3) -0.0645(17) 0.059(3) Uani 1 1 d . . . H12 H 0.4938 0.5385 0.0656 0.071 Uiso 1 1 calc R . . C13 C -0.0217(8) 0.6515(3) 0.1686(15) 0.050(2) Uani 1 1 d . . . H13 H 0.0244 0.6296 0.0706 0.060 Uiso 1 1 calc R . . C14 C -0.1182(10) 0.6800(3) 0.0322(16) 0.066(3) Uani 1 1 d . . . H14A H -0.1725 0.7004 0.1215 0.098 Uiso 1 1 calc R . . H14B H -0.1782 0.6592 -0.0455 0.098 Uiso 1 1 calc R . . H14C H -0.0656 0.6987 -0.0665 0.098 Uiso 1 1 calc R . . C15 C -0.0918(8) 0.6208(3) 0.3341(15) 0.046(2) Uani 1 1 d . . . C16 C -0.2156(10) 0.5984(3) 0.2890(19) 0.066(3) Uani 1 1 d . . . H16 H -0.2596 0.6043 0.1595 0.079 Uiso 1 1 calc R . . C17 C -0.2754(11) 0.5673(4) 0.434(2) 0.077(3) Uani 1 1 d . . . H17 H -0.3574 0.5521 0.3990 0.092 Uiso 1 1 calc R . . C18 C -0.2149(11) 0.5589(4) 0.6289(19) 0.072(3) Uani 1 1 d . . . H18 H -0.2563 0.5389 0.7278 0.087 Uiso 1 1 calc R . . C19 C -0.0920(11) 0.5809(3) 0.6738(17) 0.066(3) Uani 1 1 d . . . H19 H -0.0475 0.5749 0.8027 0.080 Uiso 1 1 calc R . . C20 C -0.0328(10) 0.6123(3) 0.5265(17) 0.064(3) Uani 1 1 d . . . H20 H 0.0489 0.6277 0.5619 0.076 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 O1 0.083(5) 0.056(4) 0.076(5) -0.009(4) -0.007(5) -0.008(4) O2 0.093(5) 0.083(5) 0.059(5) 0.001(4) -0.019(5) -0.003(5) O3 0.053(3) 0.058(4) 0.067(4) -0.002(4) 0.002(4) -0.007(3) O4 0.042(3) 0.057(4) 0.066(4) -0.001(4) 0.010(3) 0.001(3) N1 0.047(4) 0.048(4) 0.044(4) -0.009(4) -0.003(4) -0.008(3) C1 0.047(5) 0.041(5) 0.053(6) -0.009(4) 0.007(5) -0.001(4) C2 0.063(6) 0.069(7) 0.053(6) -0.003(6) 0.000(6) -0.005(5) C3 0.088(8) 0.062(6) 0.075(8) -0.002(6) 0.019(8) -0.019(6) C4 0.063(6) 0.056(5) 0.083(8) 0.011(6) 0.005(7) 0.007(5) C5 0.048(5) 0.060(6) 0.045(5) 0.013(5) 0.008(5) -0.002(5) C6 0.051(5) 0.069(6) 0.075(7) 0.007(6) 0.004(6) 0.008(5) C7 0.053(5) 0.043(5) 0.052(6) 0.005(5) 0.006(5) -0.001(5) C8 0.076(7) 0.047(5) 0.057(6) 0.020(5) -0.007(6) 0.011(5) C9 0.077(7) 0.067(7) 0.067(7) 0.008(6) -0.002(7) 0.000(6) C10 0.075(7) 0.072(7) 0.057(7) 0.005(6) 0.008(7) -0.005(6) C11 0.068(7) 0.061(6) 0.076(8) 0.006(6) 0.009(7) 0.002(5) C12 0.060(6) 0.071(6) 0.048(6) 0.003(6) 0.008(5) 0.012(5) C13 0.043(5) 0.063(5) 0.044(6) -0.011(5) -0.005(5) 0.005(4) C14 0.068(6) 0.078(7) 0.051(6) 0.007(6) -0.007(6) 0.014(6) C15 0.030(4) 0.054(5) 0.053(6) -0.004(5) -0.002(4) -0.001(4) C16 0.056(6) 0.069(6) 0.072(7) -0.003(6) -0.011(6) -0.009(5) C17 0.059(6) 0.076(7) 0.095(9) -0.009(7) -0.001(7) -0.021(6) C18 0.070(7) 0.079(7) 0.068(7) 0.001(7) 0.020(7) -0.006(6) C19 0.084(7) 0.064(6) 0.051(6) 0.000(6) 0.004(6) -0.008(6) C20 0.058(6) 0.067(6) 0.066(7) -0.007(6) -0.007(6) -0.006(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 C2 1.325(11) . ? O1 C3 1.450(13) . ? O2 C2 1.184(11) . ? O3 C5 1.221(10) . ? O4 C5 1.346(10) . ? O4 C6 1.450(10) . ? N1 C5 1.356(10) . ? N1 C1 1.470(10) . ? N1 C13 1.467(10) . ? C1 C4 1.507(12) . ? C1 C2 1.525(13) . ? C1 H1 0.9800 . ? C3 C4 1.524(14) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 C7 1.512(12) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C12 1.374(12) . ? C7 C8 1.384(13) . ? C8 C9 1.384(13) . ? C8 H8 0.9300 . ? C9 C10 1.350(13) . ? C9 H9 0.9300 . ? C10 C11 1.371(14) . ? C10 H10 0.9300 . ? C11 C12 1.370(13) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.503(12) . ? C13 C15 1.513(12) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C20 1.354(13) . ? C15 C16 1.385(12) . ? C16 C17 1.392(14) . ? C16 H16 0.9300 . ? C17 C18 1.373(15) . ? C17 H17 0.9300 . ? C18 C19 1.372(13) . ? C18 H18 0.9300 . ? C19 C20 1.404(13) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? 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 C2 O1 C3 110.8(8) . . ? C5 O4 C6 115.4(7) . . ? C5 N1 C1 116.4(7) . . ? C5 N1 C13 124.5(8) . . ? C1 N1 C13 117.8(7) . . ? N1 C1 C4 116.9(8) . . ? N1 C1 C2 112.9(8) . . ? C4 C1 C2 105.0(8) . . ? N1 C1 H1 107.2 . . ? C4 C1 H1 107.2 . . ? C2 C1 H1 107.2 . . ? O2 C2 O1 122.4(10) . . ? O2 C2 C1 127.9(9) . . ? O1 C2 C1 109.6(9) . . ? O1 C3 C4 107.0(7) . . ? O1 C3 H3A 110.3 . . ? C4 C3 H3A 110.3 . . ? O1 C3 H3B 110.3 . . ? C4 C3 H3B 110.3 . . ? H3A C3 H3B 108.6 . . ? C1 C4 C3 102.0(9) . . ? C1 C4 H4A 111.4 . . ? C3 C4 H4A 111.4 . . ? C1 C4 H4B 111.4 . . ? C3 C4 H4B 111.4 . . ? H4A C4 H4B 109.2 . . ? O3 C5 O4 124.4(8) . . ? O3 C5 N1 123.5(9) . . ? O4 C5 N1 112.1(8) . . ? O4 C6 C7 105.9(8) . . ? O4 C6 H6A 110.5 . . ? C7 C6 H6A 110.5 . . ? O4 C6 H6B 110.5 . . ? C7 C6 H6B 110.5 . . ? H6A C6 H6B 108.7 . . ? C12 C7 C8 117.8(9) . . ? C12 C7 C6 122.0(9) . . ? C8 C7 C6 120.2(8) . . ? C9 C8 C7 120.2(9) . . ? C9 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? C10 C9 C8 120.8(11) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.6(11) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 119.9(10) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 121.5(10) . . ? C11 C12 H12 119.2 . . ? C7 C12 H12 119.2 . . ? N1 C13 C14 112.1(7) . . ? N1 C13 C15 112.2(7) . . ? C14 C13 C15 114.9(7) . . ? N1 C13 H13 105.6 . . ? C14 C13 H13 105.6 . . ? C15 C13 H13 105.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C20 C15 C16 117.7(9) . . ? C20 C15 C13 121.5(8) . . ? C16 C15 C13 120.7(9) . . ? C15 C16 C17 121.1(10) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C18 C17 C16 120.8(10) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C17 C18 C19 118.3(11) . . ? C17 C18 H18 120.9 . . ? C19 C18 H18 120.9 . . ? C18 C19 C20 120.4(11) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C15 C20 C19 121.7(9) . . ? C15 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? 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 C5 N1 C1 C4 72.1(11) . . . . ? C13 N1 C1 C4 -95.8(9) . . . . ? C5 N1 C1 C2 -49.8(11) . . . . ? C13 N1 C1 C2 142.3(8) . . . . ? C3 O1 C2 O2 -177.4(10) . . . . ? C3 O1 C2 C1 1.4(11) . . . . ? N1 C1 C2 O2 -39.3(14) . . . . ? C4 C1 C2 O2 -167.7(11) . . . . ? N1 C1 C2 O1 141.9(8) . . . . ? C4 C1 C2 O1 13.6(10) . . . . ? C2 O1 C3 C4 -15.9(12) . . . . ? N1 C1 C4 C3 -147.5(8) . . . . ? C2 C1 C4 C3 -21.5(10) . . . . ? O1 C3 C4 C1 22.9(11) . . . . ? C6 O4 C5 O3 -5.2(14) . . . . ? C6 O4 C5 N1 176.7(8) . . . . ? C1 N1 C5 O3 -0.4(14) . . . . ? C13 N1 C5 O3 166.6(9) . . . . ? C1 N1 C5 O4 177.7(7) . . . . ? C13 N1 C5 O4 -15.2(13) . . . . ? C5 O4 C6 C7 -161.9(7) . . . . ? O4 C6 C7 C12 -112.8(10) . . . . ? O4 C6 C7 C8 66.4(11) . . . . ? C12 C7 C8 C9 1.0(14) . . . . ? C6 C7 C8 C9 -178.3(9) . . . . ? C7 C8 C9 C10 1.0(16) . . . . ? C8 C9 C10 C11 -2.9(16) . . . . ? C9 C10 C11 C12 2.9(16) . . . . ? C10 C11 C12 C7 -1.0(15) . . . . ? C8 C7 C12 C11 -0.9(14) . . . . ? C6 C7 C12 C11 178.3(9) . . . . ? C5 N1 C13 C14 -116.0(10) . . . . ? C1 N1 C13 C14 50.8(11) . . . . ? C5 N1 C13 C15 113.0(9) . . . . ? C1 N1 C13 C15 -80.1(9) . . . . ? N1 C13 C15 C20 -16.7(12) . . . . ? C14 C13 C15 C20 -146.3(9) . . . . ? N1 C13 C15 C16 166.6(8) . . . . ? C14 C13 C15 C16 37.0(12) . . . . ? C20 C15 C16 C17 -1.7(14) . . . . ? C13 C15 C16 C17 175.1(9) . . . . ? C15 C16 C17 C18 1.7(16) . . . . ? C16 C17 C18 C19 -2.0(17) . . . . ? C17 C18 C19 C20 2.2(15) . . . . ? C16 C15 C20 C19 2.0(14) . . . . ? C13 C15 C20 C19 -174.8(9) . . . . ? C18 C19 C20 C15 -2.3(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 60.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.355 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.081