# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name 'Russell Cox' 'Luke A. Adams' 'Jonathan Charmant' 'Magnus Walter' 'William G. Whittingham' _publ_contact_author_name 'Dr Russell Cox' _publ_contact_author_address ; School of Chemistry University of Bristol Cantock's Close Bristol BS8 1TS UNITED KINGDOM ; _publ_contact_author_email R.J.COX@BRIS.AC.UK _publ_section_title ; Efficient Synthesis of Protected Cyclopropyl B-Aspartylphosphates ; data_laaa _database_code_CSD 220087 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H35 N O6' _chemical_formula_sum 'C29 H35 N O6' _chemical_formula_weight 493.58 _chemical_absolute_configuration syn 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 5.8851(13) _cell_length_b 10.029(2) _cell_length_c 12.416(3) _cell_angle_alpha 112.711(4) _cell_angle_beta 91.376(4) _cell_angle_gamma 97.897(4) _cell_volume 667.2(3) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 797 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 18.7 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.413 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5369 _diffrn_reflns_av_R_equivalents 0.0976 _diffrn_reflns_av_sigmaI/netI 0.2395 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 24.13 _reflns_number_total 4013 _reflns_number_gt 1800 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1071P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 4013 _refine_ls_number_parameters 332 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.1821 _refine_ls_R_factor_gt 0.0891 _refine_ls_wR_factor_ref 0.2349 _refine_ls_wR_factor_gt 0.1994 _refine_ls_goodness_of_fit_ref 0.879 _refine_ls_restrained_S_all 0.879 _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 C1 C 0.9206(15) 0.7895(9) 0.7860(8) 0.031(2) Uani 1 1 d . . . H1 H 1.0709 0.8402 0.7890 0.037 Uiso 1 1 calc R . . C2 C 0.8700(17) 0.7446(10) 0.8723(8) 0.037(3) Uani 1 1 d . . . H2 H 0.9840 0.7651 0.9345 0.044 Uiso 1 1 calc R . . C3 C 0.6509(17) 0.6674(11) 0.8730(9) 0.040(3) Uani 1 1 d . . . H3 H 0.6145 0.6320 0.9322 0.048 Uiso 1 1 calc R . . C4 C 0.4903(17) 0.6465(11) 0.7800(9) 0.039(3) Uani 1 1 d . . . H4 H 0.3394 0.5974 0.7783 0.047 Uiso 1 1 calc R . . C5 C 0.5384(15) 0.6920(9) 0.6937(8) 0.032(2) Uani 1 1 d . . . H5 H 0.4211 0.6750 0.6339 0.038 Uiso 1 1 calc R . . C6 C 0.7602(16) 0.7651(10) 0.6894(8) 0.035(2) Uani 1 1 d . . . C7 C 0.8225(16) 0.8060(9) 0.5933(9) 0.034(2) Uani 1 1 d . . . C8 C 1.0093(16) 0.9307(10) 0.6191(8) 0.032(2) Uani 1 1 d . . . C9 C 1.2137(17) 0.9160(11) 0.5584(9) 0.039(3) Uani 1 1 d . . . H9 H 1.2327 0.8244 0.4998 0.046 Uiso 1 1 calc R . . C10 C 1.3839(17) 1.0371(12) 0.5860(10) 0.044(3) Uani 1 1 d . . . H10 H 1.5175 1.0271 0.5439 0.052 Uiso 1 1 calc R . . C11 C 1.3671(19) 1.1682(12) 0.6700(10) 0.050(3) Uani 1 1 d . . . H11 H 1.4888 1.2479 0.6870 0.060 Uiso 1 1 calc R . . C12 C 1.171(2) 1.1878(11) 0.7328(10) 0.049(3) Uani 1 1 d . . . H12 H 1.1564 1.2802 0.7917 0.059 Uiso 1 1 calc R . . C13 C 0.9963(17) 1.0656(10) 0.7052(8) 0.036(3) Uani 1 1 d . . . H13 H 0.8637 1.0768 0.7481 0.043 Uiso 1 1 calc R . . C14 C 0.7253(15) 0.7230(9) 0.4826(9) 0.030(2) Uani 1 1 d . . . H14 H 0.6191 0.6378 0.4727 0.036 Uiso 1 1 calc R . . C15 C 0.7684(14) 0.7521(9) 0.3777(8) 0.027(2) Uani 1 1 d . . . H15 H 0.8678 0.8474 0.3914 0.032 Uiso 1 1 calc R . . C16 C 0.5759(16) 0.7017(10) 0.2789(8) 0.037(3) Uani 1 1 d . . . H16A H 0.5592 0.7665 0.2369 0.044 Uiso 1 1 calc R . . H16B H 0.4295 0.6471 0.2883 0.044 Uiso 1 1 calc R . . C17 C 0.7910(14) 0.6249(9) 0.2606(7) 0.023(2) Uani 1 1 d U . . C18 C 0.9459(16) 0.6594(11) 0.1797(8) 0.030(2) Uani 1 1 d . . . C19 C 1.1708(16) 0.5579(11) 0.0222(8) 0.038(3) Uani 1 1 d . . . H19A H 1.0627 0.5386 -0.0454 0.057 Uiso 1 1 calc R . . H19B H 1.2796 0.4880 -0.0004 0.057 Uiso 1 1 calc R . . H19C H 1.2554 0.6578 0.0485 0.057 Uiso 1 1 calc R . . C20 C 0.9288(16) 0.4577(11) 0.3340(8) 0.029(2) Uani 1 1 d . . . C21 C 1.0007(15) 0.3003(10) 0.4359(8) 0.031(2) Uani 1 1 d . . . C22 C 1.2679(16) 0.3106(11) 0.4192(9) 0.044(3) Uani 1 1 d . . . H22A H 1.3473 0.2919 0.4810 0.065 Uiso 1 1 calc R . . H22B H 1.3295 0.4086 0.4237 0.065 Uiso 1 1 calc R . . H22C H 1.2921 0.2375 0.3425 0.065 Uiso 1 1 calc R . . C23 C 0.9600(17) 0.4087(11) 0.5529(8) 0.042(3) Uani 1 1 d . . . H23A H 0.7942 0.4090 0.5585 0.063 Uiso 1 1 calc R . . H23B H 1.0363 0.5064 0.5630 0.063 Uiso 1 1 calc R . . H23C H 1.0225 0.3820 0.6143 0.063 Uiso 1 1 calc R . . C24 C 0.9014(18) 0.1460(11) 0.4121(10) 0.050(3) Uani 1 1 d . . . H24A H 0.9686 0.1165 0.4709 0.075 Uiso 1 1 calc R . . H24B H 0.9359 0.0820 0.3339 0.075 Uiso 1 1 calc R . . H24C H 0.7342 0.1377 0.4160 0.075 Uiso 1 1 calc R . . C25 C 0.6262(16) 0.3700(9) 0.1633(9) 0.026(2) Uani 1 1 d . . . C26 C 0.4637(16) 0.1124(10) 0.0665(8) 0.036(3) Uani 1 1 d . . . C27 C 0.4719(19) -0.0067(11) 0.1085(10) 0.058(3) Uani 1 1 d . . . H27A H 0.6325 -0.0183 0.1194 0.086 Uiso 1 1 calc R . . H27B H 0.3866 -0.0985 0.0506 0.086 Uiso 1 1 calc R . . H27C H 0.4022 0.0178 0.1833 0.086 Uiso 1 1 calc R . . C28 C 0.2080(16) 0.1396(11) 0.0605(11) 0.052(3) Uani 1 1 d . . . H28A H 0.1501 0.1644 0.1381 0.077 Uiso 1 1 calc R . . H28B H 0.1125 0.0509 0.0042 0.077 Uiso 1 1 calc R . . H28C H 0.2019 0.2207 0.0355 0.077 Uiso 1 1 calc R . . C29 C 0.5642(16) 0.0903(11) -0.0467(9) 0.046(3) Uani 1 1 d . . . H29A H 0.5473 0.1732 -0.0679 0.069 Uiso 1 1 calc R . . H29B H 0.4836 -0.0004 -0.1080 0.069 Uiso 1 1 calc R . . H29C H 0.7279 0.0836 -0.0389 0.069 Uiso 1 1 calc R . . N N 0.7619(11) 0.4805(7) 0.2604(6) 0.0254(19) Uani 1 1 d . . . O1 O 0.9694(11) 0.7720(7) 0.1653(6) 0.0414(18) Uani 1 1 d . . . O2 O 1.0432(10) 0.5419(7) 0.1174(5) 0.0353(17) Uani 1 1 d . . . O3 O 1.1012(10) 0.5505(7) 0.3776(6) 0.0375(17) Uani 1 1 d . . . O4 O 0.8808(10) 0.3331(6) 0.3439(5) 0.0343(17) Uani 1 1 d . . . O5 O 0.5961(10) 0.2430(6) 0.1659(5) 0.0339(17) Uani 1 1 d . . . O6 O 0.5435(11) 0.4046(7) 0.0874(6) 0.0393(17) 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 C1 0.014(6) 0.029(5) 0.048(7) 0.015(5) -0.011(5) 0.002(4) C2 0.019(6) 0.060(7) 0.027(6) 0.015(5) -0.012(5) 0.004(5) C3 0.027(7) 0.059(7) 0.037(7) 0.020(6) 0.010(5) 0.011(5) C4 0.013(6) 0.064(7) 0.041(7) 0.026(6) 0.000(5) -0.004(5) C5 0.015(6) 0.048(6) 0.027(6) 0.008(5) 0.000(5) 0.004(5) C6 0.016(6) 0.043(6) 0.041(6) 0.012(5) -0.002(5) 0.004(5) C7 0.027(6) 0.032(6) 0.041(7) 0.014(5) 0.003(5) 0.006(5) C8 0.018(6) 0.045(6) 0.027(6) 0.009(5) -0.007(5) 0.005(4) C9 0.024(6) 0.051(7) 0.042(6) 0.019(5) 0.002(5) 0.006(5) C10 0.013(6) 0.060(8) 0.058(8) 0.027(7) -0.007(5) -0.002(5) C11 0.025(7) 0.050(8) 0.066(8) 0.021(7) -0.030(6) -0.016(5) C12 0.038(8) 0.044(7) 0.054(7) 0.011(6) -0.015(6) -0.003(6) C13 0.017(6) 0.049(7) 0.035(6) 0.008(6) -0.002(5) 0.004(5) C14 0.014(5) 0.026(5) 0.041(6) 0.006(5) 0.005(5) 0.000(4) C15 0.004(5) 0.037(6) 0.034(6) 0.013(5) -0.011(4) -0.004(4) C16 0.010(5) 0.055(7) 0.033(6) 0.005(5) -0.008(5) 0.005(5) C17 0.006(5) 0.038(5) 0.025(5) 0.013(4) -0.008(4) 0.000(4) C18 0.022(6) 0.035(6) 0.023(6) 0.003(5) -0.018(5) 0.000(5) C19 0.022(6) 0.060(7) 0.031(6) 0.015(5) 0.003(5) 0.011(5) C20 0.008(5) 0.048(6) 0.044(7) 0.030(5) 0.004(5) 0.015(5) C21 0.014(5) 0.045(6) 0.031(6) 0.012(5) -0.002(5) 0.009(5) C22 0.019(6) 0.053(7) 0.050(7) 0.013(6) -0.006(5) 0.002(5) C23 0.015(6) 0.071(8) 0.044(7) 0.026(6) -0.006(5) 0.011(5) C24 0.024(6) 0.060(7) 0.071(8) 0.034(6) -0.019(6) 0.003(5) C25 0.019(6) 0.020(5) 0.046(7) 0.018(5) 0.011(5) 0.007(4) C26 0.024(6) 0.032(6) 0.031(6) -0.009(5) -0.015(5) 0.003(4) C27 0.033(7) 0.053(7) 0.079(9) 0.020(7) -0.010(7) 0.001(5) C28 0.005(6) 0.058(7) 0.076(8) 0.011(6) -0.009(6) 0.004(5) C29 0.014(6) 0.057(7) 0.039(7) -0.008(5) -0.018(5) 0.004(5) N 0.009(4) 0.035(5) 0.031(5) 0.012(4) -0.006(4) 0.003(3) O1 0.024(4) 0.050(4) 0.057(5) 0.028(4) 0.005(3) 0.008(3) O2 0.021(4) 0.042(4) 0.036(4) 0.009(3) -0.004(3) 0.004(3) O3 0.008(4) 0.051(4) 0.050(5) 0.017(4) -0.007(3) 0.001(3) O4 0.013(4) 0.042(4) 0.052(4) 0.023(3) -0.011(3) 0.004(3) O5 0.016(4) 0.039(4) 0.039(4) 0.009(3) -0.005(3) 0.002(3) O6 0.025(4) 0.053(4) 0.042(4) 0.019(4) -0.005(3) 0.013(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 C1 C2 1.338(12) . ? C1 C6 1.430(12) . ? C1 H1 0.9500 . ? C2 C3 1.412(13) . ? C2 H2 0.9500 . ? C3 C4 1.406(13) . ? C3 H3 0.9500 . ? C4 C5 1.339(13) . ? C4 H4 0.9500 . ? C5 C6 1.420(12) . ? C5 H5 0.9500 . ? C6 C7 1.444(12) . ? C7 C14 1.363(12) . ? C7 C8 1.474(12) . ? C8 C13 1.376(12) . ? C8 C9 1.429(13) . ? C9 C10 1.387(13) . ? C9 H9 0.9500 . ? C10 C11 1.345(14) . ? C10 H10 0.9500 . ? C11 C12 1.401(15) . ? C11 H11 0.9500 . ? C12 C13 1.411(13) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.462(12) . ? C14 H14 0.9500 . ? C15 C16 1.530(12) . ? C15 C17 1.543(12) . ? C15 H15 1.0000 . ? C16 C17 1.547(12) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 N 1.434(10) . ? C17 C18 1.479(13) . ? C18 O1 1.200(10) . ? C18 O2 1.348(11) . ? C19 O2 1.464(10) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O3 1.230(11) . ? C20 O4 1.296(10) . ? C20 N 1.425(10) . ? C21 C24 1.489(12) . ? C21 C23 1.490(13) . ? C21 O4 1.492(10) . ? C21 C22 1.586(13) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O6 1.234(10) . ? C25 O5 1.276(10) . ? C25 N 1.414(11) . ? C26 C27 1.482(13) . ? C26 C29 1.486(14) . ? C26 O5 1.507(10) . ? C26 C28 1.571(13) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? 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 C1 C6 123.4(9) . . ? C2 C1 H1 118.3 . . ? C6 C1 H1 118.3 . . ? C1 C2 C3 121.4(9) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 115.5(9) . . ? C4 C3 H3 122.3 . . ? C2 C3 H3 122.3 . . ? C5 C4 C3 123.6(10) . . ? C5 C4 H4 118.2 . . ? C3 C4 H4 118.2 . . ? C4 C5 C6 121.6(9) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 114.4(9) . . ? C5 C6 C7 123.0(9) . . ? C1 C6 C7 122.6(9) . . ? C14 C7 C6 120.3(8) . . ? C14 C7 C8 122.5(9) . . ? C6 C7 C8 116.9(8) . . ? C13 C8 C9 117.2(9) . . ? C13 C8 C7 121.1(9) . . ? C9 C8 C7 121.6(9) . . ? C10 C9 C8 119.2(10) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C11 C10 C9 122.6(11) . . ? C11 C10 H10 118.7 . . ? C9 C10 H10 118.7 . . ? C10 C11 C12 120.4(10) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 117.6(10) . . ? C11 C12 H12 121.2 . . ? C13 C12 H12 121.2 . . ? C8 C13 C12 123.0(10) . . ? C8 C13 H13 118.5 . . ? C12 C13 H13 118.5 . . ? C7 C14 C15 126.3(8) . . ? C7 C14 H14 116.8 . . ? C15 C14 H14 116.8 . . ? C14 C15 C16 119.0(8) . . ? C14 C15 C17 120.0(7) . . ? C16 C15 C17 60.4(5) . . ? C14 C15 H15 115.4 . . ? C16 C15 H15 115.4 . . ? C17 C15 H15 115.4 . . ? C15 C16 C17 60.2(6) . . ? C15 C16 H16A 117.8 . . ? C17 C16 H16A 117.8 . . ? C15 C16 H16B 117.8 . . ? C17 C16 H16B 117.8 . . ? H16A C16 H16B 114.9 . . ? N C17 C18 119.0(7) . . ? N C17 C15 117.0(7) . . ? C18 C17 C15 116.8(7) . . ? N C17 C16 116.9(7) . . ? C18 C17 C16 113.7(8) . . ? C15 C17 C16 59.4(5) . . ? O1 C18 O2 124.6(9) . . ? O1 C18 C17 124.9(9) . . ? O2 C18 C17 110.3(8) . . ? O2 C19 H19A 109.5 . . ? O2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O3 C20 O4 126.8(8) . . ? O3 C20 N 119.7(8) . . ? O4 C20 N 113.4(8) . . ? C24 C21 C23 114.6(9) . . ? C24 C21 O4 104.3(7) . . ? C23 C21 O4 108.5(7) . . ? C24 C21 C22 109.3(8) . . ? C23 C21 C22 110.4(7) . . ? O4 C21 C22 109.5(7) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O6 C25 O5 126.5(9) . . ? O6 C25 N 118.5(7) . . ? O5 C25 N 115.0(8) . . ? C27 C26 C29 115.6(8) . . ? C27 C26 O5 102.1(8) . . ? C29 C26 O5 111.5(8) . . ? C27 C26 C28 109.0(9) . . ? C29 C26 C28 110.6(8) . . ? O5 C26 C28 107.5(7) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C25 N C20 125.8(7) . . ? C25 N C17 115.7(6) . . ? C20 N C17 115.0(7) . . ? C18 O2 C19 114.1(7) . . ? C20 O4 C21 122.3(7) . . ? C25 O5 C26 121.4(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 C6 C1 C2 C3 0.6(15) . . . . ? C1 C2 C3 C4 -2.2(14) . . . . ? C2 C3 C4 C5 1.7(15) . . . . ? C3 C4 C5 C6 0.5(16) . . . . ? C4 C5 C6 C1 -2.1(13) . . . . ? C4 C5 C6 C7 175.3(9) . . . . ? C2 C1 C6 C5 1.6(13) . . . . ? C2 C1 C6 C7 -175.9(9) . . . . ? C5 C6 C7 C14 -31.5(14) . . . . ? C1 C6 C7 C14 145.8(9) . . . . ? C5 C6 C7 C8 154.4(9) . . . . ? C1 C6 C7 C8 -28.4(13) . . . . ? C14 C7 C8 C13 129.4(10) . . . . ? C6 C7 C8 C13 -56.6(12) . . . . ? C14 C7 C8 C9 -52.3(13) . . . . ? C6 C7 C8 C9 121.7(10) . . . . ? C13 C8 C9 C10 -1.8(13) . . . . ? C7 C8 C9 C10 179.9(9) . . . . ? C8 C9 C10 C11 1.6(14) . . . . ? C9 C10 C11 C12 -1.0(15) . . . . ? C10 C11 C12 C13 0.7(15) . . . . ? C9 C8 C13 C12 1.7(14) . . . . ? C7 C8 C13 C12 -180.0(9) . . . . ? C11 C12 C13 C8 -1.2(14) . . . . ? C6 C7 C14 C15 178.9(8) . . . . ? C8 C7 C14 C15 -7.3(15) . . . . ? C7 C14 C15 C16 -149.9(9) . . . . ? C7 C14 C15 C17 139.5(9) . . . . ? C14 C15 C16 C17 -110.1(9) . . . . ? C14 C15 C17 N 1.6(11) . . . . ? C16 C15 C17 N -106.8(8) . . . . ? C14 C15 C17 C18 -148.7(8) . . . . ? C16 C15 C17 C18 102.9(8) . . . . ? C14 C15 C17 C16 108.4(9) . . . . ? C15 C16 C17 N 106.9(8) . . . . ? C15 C16 C17 C18 -108.2(8) . . . . ? N C17 C18 O1 173.7(8) . . . . ? C15 C17 C18 O1 -36.7(12) . . . . ? C16 C17 C18 O1 29.6(12) . . . . ? N C17 C18 O2 -1.4(10) . . . . ? C15 C17 C18 O2 148.2(7) . . . . ? C16 C17 C18 O2 -145.5(7) . . . . ? O6 C25 N C20 -158.0(8) . . . . ? O5 C25 N C20 24.2(12) . . . . ? O6 C25 N C17 -0.2(11) . . . . ? O5 C25 N C17 -178.0(7) . . . . ? O3 C20 N C25 147.1(9) . . . . ? O4 C20 N C25 -30.6(11) . . . . ? O3 C20 N C17 -10.9(12) . . . . ? O4 C20 N C17 171.4(7) . . . . ? C18 C17 N C25 -73.9(9) . . . . ? C15 C17 N C25 136.5(7) . . . . ? C16 C17 N C25 69.0(9) . . . . ? C18 C17 N C20 86.4(9) . . . . ? C15 C17 N C20 -63.2(9) . . . . ? C16 C17 N C20 -130.7(8) . . . . ? O1 C18 O2 C19 -4.3(12) . . . . ? C17 C18 O2 C19 170.9(7) . . . . ? O3 C20 O4 C21 16.3(14) . . . . ? N C20 O4 C21 -166.1(7) . . . . ? C24 C21 O4 C20 -177.5(9) . . . . ? C23 C21 O4 C20 59.9(10) . . . . ? C22 C21 O4 C20 -60.7(10) . . . . ? O6 C25 O5 C26 5.0(13) . . . . ? N C25 O5 C26 -177.4(7) . . . . ? C27 C26 O5 C25 -179.4(8) . . . . ? C29 C26 O5 C25 56.6(10) . . . . ? C28 C26 O5 C25 -64.8(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.13 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.394 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.094 data_laa2a _database_code_CSD 220088 _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C23 H25 N O4, C H Cl3' _chemical_formula_sum 'C24 H26 Cl3 N O4' _chemical_formula_weight 498.81 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 12.425(3) _cell_length_b 18.223(5) _cell_length_c 11.601(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.042(17) _cell_angle_gamma 90.00 _cell_volume 2558.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 820 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 23.7 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method none _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.387 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.884 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Frames, each covering 0.3 \% in \w' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12277 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 24.01 _reflns_number_total 4000 _reflns_number_gt 2905 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1057P)^2^+4.7009P] 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_number_reflns 4000 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0975 _refine_ls_R_factor_gt 0.0726 _refine_ls_wR_factor_ref 0.2173 _refine_ls_wR_factor_gt 0.1946 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.023 _refine_ls_shift/su_mean 0.002 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 C1 C 0.0771(3) 0.4041(2) -0.0109(3) 0.0321(9) Uani 1 1 d . . . H1 H 0.1124 0.4371 0.0493 0.039 Uiso 1 1 calc R . . C2 C 0.0324(3) 0.4308(2) -0.1231(3) 0.0380(9) Uani 1 1 d . . . H2A H 0.0375 0.4816 -0.1394 0.046 Uiso 1 1 calc R . . C3 C -0.0197(3) 0.3837(2) -0.2116(3) 0.0382(9) Uani 1 1 d . . . H3 H -0.0492 0.4018 -0.2891 0.046 Uiso 1 1 calc R . . C4 C -0.0286(3) 0.3101(2) -0.1864(3) 0.0374(9) Uani 1 1 d . . . H4 H -0.0655 0.2777 -0.2466 0.045 Uiso 1 1 calc R . . C5 C 0.0162(3) 0.2832(2) -0.0735(3) 0.0311(8) Uani 1 1 d . . . H5 H 0.0090 0.2326 -0.0569 0.037 Uiso 1 1 calc R . . C6 C 0.0716(3) 0.33013(19) 0.0156(3) 0.0272(8) Uani 1 1 d . . . C7 C 0.1283(3) 0.30168(19) 0.1345(3) 0.0278(8) Uani 1 1 d . . . C8 C 0.1290(3) 0.35056(19) 0.2381(3) 0.0301(8) Uani 1 1 d . . . C9 C 0.2281(4) 0.3700(2) 0.3159(3) 0.0391(10) Uani 1 1 d . . . H9 H 0.2960 0.3507 0.3045 0.047 Uiso 1 1 calc R . . C10 C 0.2280(4) 0.4175(2) 0.4103(4) 0.0518(12) Uani 1 1 d . . . H10 H 0.2956 0.4308 0.4626 0.062 Uiso 1 1 calc R . . C11 C 0.1302(5) 0.4450(2) 0.4272(4) 0.0569(13) Uani 1 1 d . . . H11 H 0.1304 0.4772 0.4917 0.068 Uiso 1 1 calc R . . C12 C 0.0315(4) 0.4266(2) 0.3519(4) 0.0519(12) Uani 1 1 d . . . H12 H -0.0359 0.4457 0.3649 0.062 Uiso 1 1 calc R . . C13 C 0.0306(4) 0.3802(2) 0.2568(4) 0.0388(9) Uani 1 1 d . . . H13 H -0.0375 0.3684 0.2041 0.047 Uiso 1 1 calc R . . C14 C 0.1794(3) 0.2367(2) 0.1442(3) 0.0299(8) Uani 1 1 d . . . H14 H 0.1787 0.2110 0.0728 0.036 Uiso 1 1 calc R . . C15 C 0.2372(3) 0.2007(2) 0.2562(3) 0.0304(8) Uani 1 1 d . . . H15 H 0.2062 0.2118 0.3267 0.036 Uiso 1 1 calc R . . C16 C 0.2833(3) 0.1251(2) 0.2534(3) 0.0325(9) Uani 1 1 d . . . H16A H 0.2758 0.1014 0.1751 0.039 Uiso 1 1 calc R . . H16B H 0.2771 0.0911 0.3182 0.039 Uiso 1 1 calc R . . C17 C 0.3629(3) 0.18816(19) 0.2831(3) 0.0276(8) Uani 1 1 d . . . C18 C 0.4195(3) 0.2137(2) 0.1893(3) 0.0286(8) Uani 1 1 d . . . C19 C 0.5138(3) 0.1632(2) 0.4545(3) 0.0317(9) Uani 1 1 d . . . C20 C 0.6506(3) 0.0754(2) 0.4135(3) 0.0380(9) Uani 1 1 d . . . C21 C 0.6581(4) 0.0275(3) 0.5221(5) 0.0643(15) Uani 1 1 d . . . H21A H 0.6478 0.0579 0.5885 0.096 Uiso 1 1 calc R . . H21B H 0.7308 0.0040 0.5425 0.096 Uiso 1 1 calc R . . H21C H 0.6005 -0.0102 0.5053 0.096 Uiso 1 1 calc R . . C22 C 0.7418(4) 0.1317(3) 0.4313(5) 0.0609(14) Uani 1 1 d . . . H22A H 0.7288 0.1653 0.3637 0.091 Uiso 1 1 calc R . . H22B H 0.8129 0.1068 0.4378 0.091 Uiso 1 1 calc R . . H22C H 0.7429 0.1594 0.5039 0.091 Uiso 1 1 calc R . . C23 C 0.6480(5) 0.0297(3) 0.3041(5) 0.0750(17) Uani 1 1 d . . . H23A H 0.5863 -0.0050 0.2931 0.112 Uiso 1 1 calc R . . H23B H 0.7175 0.0026 0.3134 0.112 Uiso 1 1 calc R . . H23C H 0.6384 0.0620 0.2349 0.112 Uiso 1 1 calc R . . N1 N 0.4206(2) 0.19893(17) 0.4043(2) 0.0307(7) Uani 1 1 d . . . H1A H 0.3934 0.2305 0.4475 0.037 Uiso 1 1 calc R . . O1 O 0.3913(2) 0.19442(15) 0.0870(2) 0.0369(7) Uani 1 1 d . . . O2 O 0.4986(2) 0.26238(17) 0.2279(2) 0.0409(7) Uani 1 1 d . . . O3 O 0.5668(2) 0.17537(17) 0.5554(2) 0.0463(8) Uani 1 1 d . . . O4 O 0.5418(2) 0.11333(14) 0.3826(2) 0.0366(7) Uani 1 1 d . . . C24 C -0.3432(5) 0.3505(3) 0.4305(5) 0.0688(15) Uani 1 1 d . . . H24 H -0.3918 0.3066 0.4088 0.083 Uiso 1 1 calc R . . Cl1 Cl -0.2541(2) 0.35281(19) 0.3372(2) 0.1492(11) Uani 1 1 d . . . Cl2 Cl -0.4269(2) 0.42523(13) 0.4228(3) 0.1573(12) Uani 1 1 d . . . Cl3 Cl -0.2678(2) 0.33770(13) 0.57467(16) 0.1242(8) Uani 1 1 d . . . H2 H 0.522(7) 0.278(5) 0.179(7) 0.149 Uiso 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 C1 0.030(2) 0.033(2) 0.033(2) 0.0020(16) 0.0078(16) -0.0013(15) C2 0.038(2) 0.037(2) 0.039(2) 0.0109(18) 0.0099(18) 0.0027(17) C3 0.037(2) 0.049(2) 0.027(2) 0.0097(18) 0.0054(17) 0.0101(18) C4 0.034(2) 0.044(2) 0.032(2) -0.0046(17) 0.0032(17) 0.0081(18) C5 0.031(2) 0.0302(19) 0.032(2) 0.0003(16) 0.0063(16) 0.0066(15) C6 0.0239(18) 0.032(2) 0.0269(19) 0.0028(15) 0.0083(15) 0.0057(15) C7 0.0250(18) 0.032(2) 0.0270(19) 0.0036(15) 0.0076(14) 0.0016(15) C8 0.040(2) 0.0257(19) 0.0256(19) 0.0071(15) 0.0091(16) 0.0001(16) C9 0.050(3) 0.034(2) 0.031(2) 0.0042(17) 0.0043(18) 0.0003(18) C10 0.080(4) 0.039(2) 0.031(2) 0.0008(18) 0.001(2) -0.003(2) C11 0.103(4) 0.041(2) 0.028(2) -0.0001(19) 0.018(3) 0.010(3) C12 0.078(3) 0.040(2) 0.045(3) 0.008(2) 0.030(3) 0.017(2) C13 0.046(2) 0.033(2) 0.040(2) 0.0062(17) 0.0170(19) 0.0062(18) C14 0.0264(18) 0.035(2) 0.0288(19) 0.0027(15) 0.0071(15) 0.0024(16) C15 0.0296(19) 0.035(2) 0.0277(19) 0.0047(16) 0.0096(15) 0.0050(16) C16 0.037(2) 0.030(2) 0.031(2) 0.0071(16) 0.0082(16) 0.0030(16) C17 0.0292(19) 0.0330(19) 0.0216(18) 0.0038(15) 0.0075(15) 0.0080(15) C18 0.0271(19) 0.035(2) 0.023(2) -0.0006(15) 0.0046(15) 0.0028(16) C19 0.032(2) 0.043(2) 0.022(2) 0.0049(16) 0.0098(16) 0.0069(17) C20 0.033(2) 0.043(2) 0.039(2) 0.0044(17) 0.0105(17) 0.0141(17) C21 0.051(3) 0.069(3) 0.078(4) 0.036(3) 0.025(3) 0.025(2) C22 0.043(3) 0.068(3) 0.080(4) 0.001(3) 0.031(3) 0.006(2) C23 0.077(4) 0.081(4) 0.063(3) -0.018(3) 0.008(3) 0.044(3) N1 0.0335(17) 0.0402(18) 0.0192(15) 0.0010(13) 0.0077(13) 0.0120(14) O1 0.0393(15) 0.0500(16) 0.0218(15) -0.0050(12) 0.0078(11) -0.0070(12) O2 0.0403(16) 0.0592(19) 0.0233(14) -0.0020(12) 0.0074(12) -0.0151(14) O3 0.0361(15) 0.077(2) 0.0244(15) -0.0038(13) 0.0037(12) 0.0203(14) O4 0.0361(15) 0.0418(15) 0.0307(14) 0.0004(12) 0.0049(11) 0.0146(12) C24 0.065(3) 0.075(4) 0.057(3) -0.013(3) -0.007(3) -0.013(3) Cl1 0.1180(18) 0.231(3) 0.1058(17) -0.0091(17) 0.0397(14) -0.0553(18) Cl2 0.1255(18) 0.1029(16) 0.199(3) -0.0382(16) -0.0576(18) 0.0347(13) Cl3 0.1450(19) 0.1277(17) 0.0701(12) -0.0118(10) -0.0382(11) 0.0035(13) _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 C1 C2 1.383(5) . ? C1 C6 1.388(5) . ? C1 H1 0.9500 . ? C2 C3 1.382(6) . ? C2 H2A 0.9500 . ? C3 C4 1.383(6) . ? C3 H3 0.9500 . ? C4 C5 1.392(5) . ? C4 H4 0.9500 . ? C5 C6 1.398(5) . ? C5 H5 0.9500 . ? C6 C7 1.493(5) . ? C7 C14 1.337(5) . ? C7 C8 1.495(5) . ? C8 C13 1.397(6) . ? C8 C9 1.398(6) . ? C9 C10 1.396(6) . ? C9 H9 0.9500 . ? C10 C11 1.369(7) . ? C10 H10 0.9500 . ? C11 C12 1.377(7) . ? C11 H11 0.9500 . ? C12 C13 1.388(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.487(5) . ? C14 H14 0.9500 . ? C15 C16 1.495(5) . ? C15 C17 1.539(5) . ? C15 H15 1.0000 . ? C16 C17 1.505(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 N1 1.440(5) . ? C17 C18 1.497(5) . ? C18 O1 1.211(4) . ? C18 O2 1.324(5) . ? C19 O3 1.226(4) . ? C19 O4 1.332(4) . ? C19 N1 1.341(5) . ? C20 O4 1.488(4) . ? C20 C22 1.507(6) . ? C20 C23 1.511(6) . ? C20 C21 1.517(6) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N1 H1A 0.8800 . ? O2 H2 0.75(8) . ? C24 Cl2 1.703(6) . ? C24 Cl1 1.714(6) . ? C24 Cl3 1.738(5) . ? C24 H24 1.0000 . ? 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 C1 C6 121.3(4) . . ? C2 C1 H1 119.3 . . ? C6 C1 H1 119.3 . . ? C3 C2 C1 120.2(4) . . ? C3 C2 H2A 119.9 . . ? C1 C2 H2A 119.9 . . ? C2 C3 C4 119.5(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.4(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 118.2(3) . . ? C1 C6 C7 120.3(3) . . ? C5 C6 C7 121.4(3) . . ? C14 C7 C6 120.2(3) . . ? C14 C7 C8 122.9(3) . . ? C6 C7 C8 116.9(3) . . ? C13 C8 C9 118.4(4) . . ? C13 C8 C7 120.6(3) . . ? C9 C8 C7 121.0(3) . . ? C10 C9 C8 120.4(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C11 C10 C9 119.9(5) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? C10 C11 C12 120.8(4) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C11 C12 C13 120.0(4) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C12 C13 C8 120.6(4) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? C7 C14 C15 126.3(3) . . ? C7 C14 H14 116.9 . . ? C15 C14 H14 116.9 . . ? C14 C15 C16 119.9(3) . . ? C14 C15 C17 120.7(3) . . ? C16 C15 C17 59.5(2) . . ? C14 C15 H15 115.2 . . ? C16 C15 H15 115.2 . . ? C17 C15 H15 115.2 . . ? C15 C16 C17 61.7(2) . . ? C15 C16 H16A 117.6 . . ? C17 C16 H16A 117.6 . . ? C15 C16 H16B 117.6 . . ? C17 C16 H16B 117.6 . . ? H16A C16 H16B 114.7 . . ? N1 C17 C18 117.1(3) . . ? N1 C17 C16 119.0(3) . . ? C18 C17 C16 117.6(3) . . ? N1 C17 C15 115.9(3) . . ? C18 C17 C15 115.4(3) . . ? C16 C17 C15 58.8(2) . . ? O1 C18 O2 123.7(3) . . ? O1 C18 C17 122.8(3) . . ? O2 C18 C17 113.4(3) . . ? O3 C19 O4 124.1(3) . . ? O3 C19 N1 123.5(3) . . ? O4 C19 N1 112.4(3) . . ? O4 C20 C22 109.3(3) . . ? O4 C20 C23 102.0(3) . . ? C22 C20 C23 111.3(4) . . ? O4 C20 C21 110.4(3) . . ? C22 C20 C21 112.0(4) . . ? C23 C20 C21 111.5(4) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C19 N1 C17 123.3(3) . . ? C19 N1 H1A 118.4 . . ? C17 N1 H1A 118.4 . . ? C18 O2 H2 113(7) . . ? C19 O4 C20 121.2(3) . . ? Cl2 C24 Cl1 114.9(4) . . ? Cl2 C24 Cl3 110.4(3) . . ? Cl1 C24 Cl3 109.0(3) . . ? Cl2 C24 H24 107.4 . . ? Cl1 C24 H24 107.4 . . ? Cl3 C24 H24 107.4 . . ? 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 C6 C1 C2 C3 0.4(6) . . . . ? C1 C2 C3 C4 1.2(6) . . . . ? C2 C3 C4 C5 -1.1(6) . . . . ? C3 C4 C5 C6 -0.6(5) . . . . ? C2 C1 C6 C5 -2.0(5) . . . . ? C2 C1 C6 C7 175.0(3) . . . . ? C4 C5 C6 C1 2.2(5) . . . . ? C4 C5 C6 C7 -174.9(3) . . . . ? C1 C6 C7 C14 -141.0(4) . . . . ? C5 C6 C7 C14 36.0(5) . . . . ? C1 C6 C7 C8 36.3(5) . . . . ? C5 C6 C7 C8 -146.7(3) . . . . ? C14 C7 C8 C13 -130.3(4) . . . . ? C6 C7 C8 C13 52.5(5) . . . . ? C14 C7 C8 C9 52.1(5) . . . . ? C6 C7 C8 C9 -125.1(4) . . . . ? C13 C8 C9 C10 0.4(5) . . . . ? C7 C8 C9 C10 178.0(3) . . . . ? C8 C9 C10 C11 0.4(6) . . . . ? C9 C10 C11 C12 -0.3(7) . . . . ? C10 C11 C12 C13 -0.6(7) . . . . ? C11 C12 C13 C8 1.3(6) . . . . ? C9 C8 C13 C12 -1.2(5) . . . . ? C7 C8 C13 C12 -178.8(3) . . . . ? C6 C7 C14 C15 -178.7(3) . . . . ? C8 C7 C14 C15 4.2(6) . . . . ? C7 C14 C15 C16 175.4(3) . . . . ? C7 C14 C15 C17 -114.5(4) . . . . ? C14 C15 C16 C17 110.1(4) . . . . ? C15 C16 C17 N1 104.4(3) . . . . ? C15 C16 C17 C18 -104.4(3) . . . . ? C14 C15 C17 N1 141.5(3) . . . . ? C16 C15 C17 N1 -109.6(3) . . . . ? C14 C15 C17 C18 -0.6(5) . . . . ? C16 C15 C17 C18 108.3(3) . . . . ? C14 C15 C17 C16 -108.9(4) . . . . ? N1 C17 C18 O1 164.1(3) . . . . ? C16 C17 C18 O1 12.2(5) . . . . ? C15 C17 C18 O1 -54.3(5) . . . . ? N1 C17 C18 O2 -19.6(4) . . . . ? C16 C17 C18 O2 -171.4(3) . . . . ? C15 C17 C18 O2 122.1(3) . . . . ? O3 C19 N1 C17 175.5(4) . . . . ? O4 C19 N1 C17 -4.5(5) . . . . ? C18 C17 N1 C19 -67.6(5) . . . . ? C16 C17 N1 C19 83.8(4) . . . . ? C15 C17 N1 C19 150.9(3) . . . . ? O3 C19 O4 C20 -9.2(6) . . . . ? N1 C19 O4 C20 170.8(3) . . . . ? C22 C20 O4 C19 -58.1(5) . . . . ? C23 C20 O4 C19 -176.0(4) . . . . ? C21 C20 O4 C19 65.5(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.01 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.420 _refine_diff_density_min -1.004 _refine_diff_density_rms 0.069