# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_s3620p _database_code_depnum_ccdc_archive 'CCDC 913266' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H12 Cl F2 N O3' _chemical_formula_weight 207.61 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' F F 0.0171 0.0103 '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 5.8270(9) _cell_length_b 9.2591(14) _cell_length_c 8.8013(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.300(3) _cell_angle_gamma 90.00 _cell_volume 474.85(12) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1098 _cell_measurement_theta_min 3.1925 _cell_measurement_theta_max 27.7255 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.452 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 2984 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 28.22 _reflns_number_total 1171 _reflns_number_gt 967 _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^)+(0.0308P)^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 1171 _refine_ls_number_parameters 70 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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 0.5477(3) 0.61436(15) 0.18497(16) 0.0164(3) Uani 1 1 d . . . H1A H 0.6266 0.6162 0.0856 0.020 Uiso 1 1 calc R . . H1B H 0.6651 0.6078 0.2664 0.020 Uiso 1 1 calc R . . C2 C 0.4036(3) 0.7500 0.2050(2) 0.0119(4) Uani 1 2 d S . . C3 C 0.2057(3) 0.7500 0.0901(2) 0.0160(4) Uani 1 2 d S . . C4 C 0.1190(4) 0.7500 -0.1723(2) 0.0335(6) Uani 1 2 d S . . H4A H 0.1987 0.7500 -0.2701 0.050 Uiso 1 2 calc SR . . H4B H 0.0226 0.8364 -0.1648 0.050 Uiso 0.50 1 calc PR . . H4C H 0.0226 0.6636 -0.1648 0.050 Uiso 0.50 1 calc PR . . Cl1 Cl 0.0000 0.0000 0.5000 0.01784(15) Uani 1 2 d S . . F1 F 0.39836(17) 0.49656(8) 0.19230(10) 0.0255(2) Uani 1 1 d . . . N1 N 0.3010(3) 0.7500 0.35968(16) 0.0124(3) Uani 1 2 d S . . H1C H 0.4149 0.7500 0.4308 0.019 Uiso 1 2 calc SR . . H1D H 0.2126 0.6698 0.3714 0.019 Uiso 0.50 1 calc PR . . H1E H 0.2126 0.8302 0.3714 0.019 Uiso 0.50 1 calc PR . . O1 O 0.0073(3) 0.7500 0.12568(16) 0.0266(4) Uani 1 2 d S . . O2 O 0.2872(2) 0.7500 -0.04909(15) 0.0209(4) Uani 1 2 d S . . O3 O 0.3578(3) 0.2500 0.43102(18) 0.0219(4) Uani 1 2 d S . . H3B H 0.271(3) 0.1797(18) 0.4346(18) 0.033 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 0.0158(7) 0.0165(8) 0.0169(7) -0.0013(6) 0.0024(6) 0.0003(6) C2 0.0120(9) 0.0142(10) 0.0094(9) 0.000 0.0005(7) 0.000 C3 0.0186(10) 0.0132(10) 0.0160(10) 0.000 0.0003(9) 0.000 C4 0.0349(14) 0.0500(16) 0.0155(11) 0.000 -0.0099(10) 0.000 Cl1 0.0198(3) 0.0143(3) 0.0195(3) -0.00169(19) 0.0047(2) 0.0025(2) F1 0.0318(5) 0.0132(5) 0.0315(5) -0.0026(4) 0.0101(4) -0.0029(4) N1 0.0128(8) 0.0113(8) 0.0130(8) 0.000 0.0016(6) 0.000 O1 0.0130(7) 0.0451(10) 0.0217(8) 0.000 -0.0001(6) 0.000 O2 0.0194(8) 0.0322(9) 0.0110(7) 0.000 -0.0017(6) 0.000 O3 0.0227(9) 0.0158(8) 0.0270(9) 0.000 -0.0067(7) 0.000 _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 F1 1.3972(16) . ? C1 C2 1.5215(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 N1 1.490(2) . ? C2 C1 1.5214(17) 4_575 ? C2 C3 1.530(3) . ? C3 O1 1.199(2) . ? C3 O2 1.316(2) . ? C4 O2 1.458(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? N1 H1C 0.9100 . ? N1 H1D 0.9100 . ? N1 H1E 0.9100 . ? O3 H3B 0.826(16) . ? 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 F1 C1 C2 107.14(11) . . ? F1 C1 H1A 110.3 . . ? C2 C1 H1A 110.3 . . ? F1 C1 H1B 110.3 . . ? C2 C1 H1B 110.3 . . ? H1A C1 H1B 108.5 . . ? N1 C2 C1 109.29(10) . 4_575 ? N1 C2 C1 109.28(10) . . ? C1 C2 C1 111.27(16) 4_575 . ? N1 C2 C3 107.41(15) . . ? C1 C2 C3 109.75(10) 4_575 . ? C1 C2 C3 109.75(10) . . ? O1 C3 O2 126.61(18) . . ? O1 C3 C2 123.47(18) . . ? O2 C3 C2 109.92(17) . . ? O2 C4 H4A 109.5 . . ? O2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C2 N1 H1C 109.5 . . ? C2 N1 H1D 109.5 . . ? H1C N1 H1D 109.5 . . ? C2 N1 H1E 109.5 . . ? H1C N1 H1E 109.5 . . ? H1D N1 H1E 109.5 . . ? C3 O2 C4 116.61(17) . . ? 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 F1 C1 C2 N1 64.19(15) . . . . ? F1 C1 C2 C1 -175.04(9) . . . 4_575 ? F1 C1 C2 C3 -53.36(16) . . . . ? N1 C2 C3 O1 0.0 . . . . ? C1 C2 C3 O1 -118.71(10) 4_575 . . . ? C1 C2 C3 O1 118.71(10) . . . . ? N1 C2 C3 O2 180.0 . . . . ? C1 C2 C3 O2 61.29(10) 4_575 . . . ? C1 C2 C3 O2 -61.29(10) . . . . ? O1 C3 O2 C4 0.0 . . . . ? C2 C3 O2 C4 180.0 . . . . ? 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 O3 H3B Cl1 0.826(16) 2.365(16) 3.1759(12) 166.9(15) . N1 H1E Cl1 0.91 2.30 3.1594(11) 156.8 1_565 N1 H1D Cl1 0.91 2.30 3.1594(11) 156.8 2_556 N1 H1C O3 0.91 1.79 2.704(2) 179.3 3_666 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.337 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.062 data_s3673ma _database_code_depnum_ccdc_archive 'CCDC 913267' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C43 H67 Cl3 F4 N10 O12' _chemical_formula_weight 1098.42 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' F F 0.0727 0.0534 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 31.8762(15) _cell_length_b 11.7398(6) _cell_length_c 16.4074(8) _cell_angle_alpha 90.00 _cell_angle_beta 116.395(2) _cell_angle_gamma 90.00 _cell_volume 5499.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9969 _cell_measurement_theta_min 3.22 _cell_measurement_theta_max 72.36 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2312 _exptl_absorpt_coefficient_mu 2.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.54824 _exptl_absorpt_correction_T_max 0.6694 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15066 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_h_max 36 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 72.35 _reflns_number_total 5333 _reflns_number_gt 4997 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0672P)^2^+13.6933P] 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 5333 _refine_ls_number_parameters 345 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_gt 0.0521 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1348 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.90774(6) 0.32466(16) 0.91417(13) 0.0154(4) Uani 1 1 d . . . C2 C 0.90107(7) 0.35711(18) 0.81878(14) 0.0221(4) Uani 1 1 d . . . H2A H 0.9202 0.3070 0.8010 0.033 Uiso 1 1 calc R . . H2B H 0.9108 0.4364 0.8189 0.033 Uiso 1 1 calc R . . H2C H 0.8680 0.3488 0.7754 0.033 Uiso 1 1 calc R . . C3 C 0.95955(7) 0.33258(19) 0.98278(14) 0.0226(4) Uani 1 1 d . . . H3A H 0.9633 0.3100 1.0432 0.034 Uiso 1 1 calc R . . H3B H 0.9705 0.4111 0.9851 0.034 Uiso 1 1 calc R . . H3C H 0.9780 0.2817 0.9640 0.034 Uiso 1 1 calc R . . C4 C 0.88107(6) 0.41405(16) 0.94189(12) 0.0142(4) Uani 1 1 d . . . C5 C 0.82019(6) 0.44480(15) 0.99331(12) 0.0137(4) Uani 1 1 d . . . C6 C 0.77699(7) 0.37712(17) 0.98329(13) 0.0176(4) Uani 1 1 d . . . H6A H 0.7583 0.3563 0.9193 0.026 Uiso 1 1 calc R . . H6B H 0.7580 0.4240 1.0037 0.026 Uiso 1 1 calc R . . H6C H 0.7870 0.3079 1.0204 0.026 Uiso 1 1 calc R . . C7 C 0.85043(7) 0.47666(18) 1.09289(13) 0.0221(4) Uani 1 1 d . . . H7A H 0.8599 0.4073 1.1299 0.033 Uiso 1 1 calc R . . H7B H 0.8324 0.5255 1.1142 0.033 Uiso 1 1 calc R . . H7C H 0.8783 0.5177 1.0984 0.033 Uiso 1 1 calc R . . C8 C 0.80407(6) 0.55471(15) 0.93564(12) 0.0118(3) Uani 1 1 d . . . C9 C 0.75835(6) 0.63428(15) 0.78197(12) 0.0136(4) Uani 1 1 d . . . C10 C 0.71806(7) 0.68062(18) 0.79886(15) 0.0236(4) Uani 1 1 d . . . H10A H 0.6954 0.6196 0.7897 0.035 Uiso 1 1 calc R . . H10B H 0.7026 0.7430 0.7563 0.035 Uiso 1 1 calc R . . H10C H 0.7304 0.7089 0.8614 0.035 Uiso 1 1 calc R . . C11 C 0.74013(7) 0.58671(17) 0.68534(13) 0.0221(4) Uani 1 1 d . . . H11A H 0.7665 0.5575 0.6759 0.033 Uiso 1 1 calc R . . H11B H 0.7243 0.6474 0.6412 0.033 Uiso 1 1 calc R . . H11C H 0.7180 0.5248 0.6770 0.033 Uiso 1 1 calc R . . C12 C 0.79228(6) 0.73150(15) 0.78932(11) 0.0121(3) Uani 1 1 d . . . C13 C 0.87411(6) 0.78641(15) 0.82743(12) 0.0120(3) Uani 1 1 d . . . C14 C 0.92030(6) 0.72108(16) 0.85610(14) 0.0173(4) Uani 1 1 d . . . H14A H 0.9282 0.6815 0.9137 0.026 Uiso 1 1 calc R . . H14B H 0.9454 0.7747 0.8639 0.026 Uiso 1 1 calc R . . H14C H 0.9168 0.6653 0.8090 0.026 Uiso 1 1 calc R . . C15 C 0.86265(7) 0.84997(16) 0.73880(13) 0.0174(4) Uani 1 1 d . . . H15A H 0.8572 0.7949 0.6902 0.026 Uiso 1 1 calc R . . H15B H 0.8890 0.8995 0.7468 0.026 Uiso 1 1 calc R . . H15C H 0.8345 0.8963 0.7225 0.026 Uiso 1 1 calc R . . C16 C 0.88265(6) 0.87104(15) 0.90469(12) 0.0122(3) Uani 1 1 d . . . C17 C 0.88100(6) 0.90430(15) 1.05037(12) 0.0131(4) Uani 1 1 d . . . C18 C 0.88171(7) 0.82254(16) 1.12385(12) 0.0161(4) Uani 1 1 d . . . H18A H 0.8511 0.7837 1.1024 0.019 Uiso 1 1 calc R . . H18B H 0.9062 0.7639 1.1370 0.019 Uiso 1 1 calc R . . C19 C 0.84272(7) 0.99399(17) 1.02743(13) 0.0185(4) Uani 1 1 d . . . H19A H 0.8485 1.0394 1.0822 0.022 Uiso 1 1 calc R . . H19B H 0.8427 1.0462 0.9800 0.022 Uiso 1 1 calc R . . C20 C 0.92801(7) 0.96775(17) 1.08627(12) 0.0161(4) Uani 1 1 d . . . C21 C 1.00859(8) 0.9526(2) 1.13121(17) 0.0327(5) Uani 1 1 d . . . H21A H 1.0079 1.0055 1.0844 0.049 Uiso 1 1 calc R . . H21B H 1.0328 0.8948 1.1429 0.049 Uiso 1 1 calc R . . H21C H 1.0157 0.9947 1.1874 0.049 Uiso 1 1 calc R . . F1 F 0.89096(4) 0.88509(10) 1.20239(7) 0.0207(3) Uani 1 1 d . . . F2 F 0.79978(4) 0.93821(11) 0.99605(9) 0.0260(3) Uani 1 1 d . . . N1 N 0.88835(6) 0.21118(14) 0.91332(13) 0.0210(4) Uani 1 1 d D . . H1A H 0.8863(9) 0.173(2) 0.8636(16) 0.025 Uiso 1 1 d D . . H1B H 0.9087(9) 0.174(2) 0.9647(15) 0.025 Uiso 1 1 d D . . N2 N 0.84648(5) 0.37319(13) 0.95906(11) 0.0150(3) Uani 1 1 d . . . N3 N 0.78206(5) 0.53986(12) 0.84476(10) 0.0121(3) Uani 1 1 d . . . N4 N 0.83776(5) 0.70293(12) 0.81767(10) 0.0113(3) Uani 1 1 d . . . N5 N 0.87254(5) 0.83333(13) 0.97190(10) 0.0126(3) Uani 1 1 d . . . O1 O 0.89079(5) 0.51611(11) 0.94621(9) 0.0174(3) Uani 1 1 d . . . O2 O 0.81043(4) 0.64925(11) 0.97142(9) 0.0146(3) Uani 1 1 d . . . O3 O 0.77695(5) 0.82785(11) 0.76421(9) 0.0169(3) Uani 1 1 d . . . O4 O 0.90115(5) 0.96364(11) 0.90833(9) 0.0180(3) Uani 1 1 d . . . O5 O 0.93210(5) 1.06789(12) 1.10422(10) 0.0225(3) Uani 1 1 d . . . O6 O 0.96322(5) 0.89734(12) 1.09990(10) 0.0211(3) Uani 1 1 d . . . Cl1 Cl 1.02317(2) 0.41846(7) 0.84899(4) 0.0484(2) Uani 1 1 d . . . Cl2 Cl 1.0000 0.63107(11) 0.7500 0.0733(4) Uani 1 2 d S . . C22 C 0.98556(16) 0.4903(5) 0.7530(3) 0.0324(10) Uani 0.50 1 d P . -1 H22 H 0.9545 0.4905 0.7542 0.039 Uiso 0.50 1 calc PR . -1 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 0.0132(8) 0.0133(9) 0.0180(9) 0.0009(7) 0.0054(7) 0.0000(7) C2 0.0247(10) 0.0218(10) 0.0200(10) -0.0008(8) 0.0101(8) -0.0029(8) C3 0.0137(9) 0.0256(10) 0.0240(10) -0.0040(8) 0.0042(8) 0.0035(8) C4 0.0110(8) 0.0144(9) 0.0133(8) 0.0040(7) 0.0019(7) 0.0011(6) C5 0.0146(8) 0.0136(8) 0.0128(8) 0.0024(7) 0.0060(7) -0.0003(7) C6 0.0177(9) 0.0171(9) 0.0202(9) 0.0030(7) 0.0104(8) -0.0025(7) C7 0.0252(10) 0.0235(10) 0.0131(9) 0.0029(8) 0.0044(8) -0.0040(8) C8 0.0093(8) 0.0131(8) 0.0149(8) 0.0002(7) 0.0072(7) -0.0012(6) C9 0.0122(8) 0.0112(8) 0.0139(8) 0.0023(7) 0.0026(7) -0.0001(6) C10 0.0135(9) 0.0230(10) 0.0335(11) 0.0087(9) 0.0099(8) 0.0046(7) C11 0.0266(10) 0.0163(9) 0.0132(9) 0.0015(7) -0.0005(8) -0.0067(8) C12 0.0142(8) 0.0115(8) 0.0091(7) -0.0013(6) 0.0037(6) -0.0005(6) C13 0.0138(8) 0.0099(8) 0.0136(8) 0.0001(7) 0.0072(7) -0.0015(6) C14 0.0157(9) 0.0145(9) 0.0255(10) 0.0007(7) 0.0126(8) 0.0003(7) C15 0.0244(10) 0.0153(9) 0.0141(9) 0.0001(7) 0.0101(7) -0.0038(7) C16 0.0108(8) 0.0122(8) 0.0129(8) 0.0008(7) 0.0044(7) 0.0011(6) C17 0.0148(8) 0.0127(8) 0.0105(8) -0.0012(7) 0.0044(7) -0.0004(7) C18 0.0211(9) 0.0159(9) 0.0109(8) -0.0019(7) 0.0069(7) -0.0014(7) C19 0.0193(9) 0.0192(9) 0.0144(8) -0.0014(7) 0.0052(7) 0.0035(7) C20 0.0180(9) 0.0183(9) 0.0097(8) -0.0002(7) 0.0041(7) -0.0012(7) C21 0.0155(10) 0.0438(14) 0.0340(12) -0.0096(10) 0.0067(9) -0.0060(9) F1 0.0291(6) 0.0211(6) 0.0109(5) -0.0031(4) 0.0080(5) -0.0020(5) F2 0.0149(6) 0.0342(7) 0.0277(6) 0.0003(5) 0.0085(5) 0.0030(5) N1 0.0201(8) 0.0131(8) 0.0287(9) 0.0017(7) 0.0098(7) 0.0005(6) N2 0.0124(7) 0.0132(7) 0.0188(8) 0.0031(6) 0.0065(6) 0.0003(6) N3 0.0120(7) 0.0102(7) 0.0124(7) 0.0014(6) 0.0039(6) -0.0001(5) N4 0.0128(7) 0.0089(7) 0.0125(7) 0.0001(5) 0.0059(6) -0.0013(5) N5 0.0147(7) 0.0126(7) 0.0103(7) -0.0022(6) 0.0055(6) -0.0015(6) O1 0.0155(6) 0.0116(6) 0.0248(7) 0.0030(5) 0.0086(5) -0.0008(5) O2 0.0170(6) 0.0129(6) 0.0164(6) -0.0029(5) 0.0096(5) -0.0030(5) O3 0.0169(6) 0.0114(6) 0.0201(7) 0.0023(5) 0.0062(5) 0.0023(5) O4 0.0244(7) 0.0120(6) 0.0190(7) -0.0016(5) 0.0110(6) -0.0053(5) O5 0.0269(7) 0.0163(7) 0.0206(7) -0.0051(5) 0.0073(6) -0.0051(6) O6 0.0140(7) 0.0231(7) 0.0215(7) -0.0015(6) 0.0036(5) -0.0006(5) Cl1 0.0307(3) 0.0786(5) 0.0353(3) 0.0159(3) 0.0141(3) 0.0057(3) Cl2 0.1201(12) 0.0556(7) 0.0669(8) 0.000 0.0621(8) 0.000 C22 0.022(2) 0.050(3) 0.030(2) -0.003(2) 0.0161(19) -0.0007(19) _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 N1 1.466(2) . ? C1 C2 1.531(3) . ? C1 C3 1.533(3) . ? C1 C4 1.541(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 O1 1.232(2) . ? C4 N2 1.342(2) . ? C5 N2 1.464(2) . ? C5 C7 1.529(3) . ? C5 C6 1.534(2) . ? C5 C8 1.547(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 O2 1.230(2) . ? C8 N3 1.348(2) . ? C9 N3 1.473(2) . ? C9 C10 1.529(3) . ? C9 C11 1.531(3) . ? C9 C12 1.540(2) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 O3 1.228(2) . ? C12 N4 1.353(2) . ? C13 N4 1.471(2) . ? C13 C15 1.527(2) . ? C13 C14 1.537(2) . ? C13 C16 1.537(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 O4 1.226(2) . ? C16 N5 1.353(2) . ? C17 N5 1.455(2) . ? C17 C19 1.527(3) . ? C17 C18 1.533(2) . ? C17 C20 1.537(3) . ? C18 F1 1.396(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 F2 1.393(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O5 1.205(2) . ? C20 O6 1.330(2) . ? C21 O6 1.455(3) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N1 H1A 0.91(2) . ? N1 H1B 0.92(2) . ? Cl1 C22 1.717(5) . ? Cl1 C22 1.782(5) 2_756 ? Cl2 C22 1.722(6) . ? Cl2 C22 1.722(6) 2_756 ? C22 Cl1 1.782(5) 2_756 ? C22 H22 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 N1 C1 C2 110.49(16) . . ? N1 C1 C3 111.97(16) . . ? C2 C1 C3 110.50(16) . . ? N1 C1 C4 109.64(15) . . ? C2 C1 C4 106.75(15) . . ? C3 C1 C4 107.31(15) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 N2 123.00(17) . . ? O1 C4 C1 121.45(16) . . ? N2 C4 C1 115.53(16) . . ? N2 C5 C7 110.73(15) . . ? N2 C5 C6 107.53(15) . . ? C7 C5 C6 110.53(15) . . ? N2 C5 C8 109.60(14) . . ? C7 C5 C8 109.26(15) . . ? C6 C5 C8 109.16(14) . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O2 C8 N3 122.64(16) . . ? O2 C8 C5 121.44(16) . . ? N3 C8 C5 115.91(15) . . ? N3 C9 C10 110.62(15) . . ? N3 C9 C11 106.87(15) . . ? C10 C9 C11 110.79(16) . . ? N3 C9 C12 112.26(14) . . ? C10 C9 C12 109.84(15) . . ? C11 C9 C12 106.34(15) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 N4 123.31(16) . . ? O3 C12 C9 119.69(16) . . ? N4 C12 C9 116.82(15) . . ? N4 C13 C15 112.23(14) . . ? N4 C13 C14 107.58(14) . . ? C15 C13 C14 109.05(15) . . ? N4 C13 C16 111.26(14) . . ? C15 C13 C16 110.44(14) . . ? C14 C13 C16 106.02(14) . . ? 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 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O4 C16 N5 122.30(17) . . ? O4 C16 C13 121.23(16) . . ? N5 C16 C13 116.21(15) . . ? N5 C17 C19 111.31(15) . . ? N5 C17 C18 105.64(14) . . ? C19 C17 C18 110.88(15) . . ? N5 C17 C20 112.48(15) . . ? C19 C17 C20 107.24(15) . . ? C18 C17 C20 109.34(14) . . ? F1 C18 C17 108.65(15) . . ? F1 C18 H18A 110.0 . . ? C17 C18 H18A 110.0 . . ? F1 C18 H18B 110.0 . . ? C17 C18 H18B 110.0 . . ? H18A C18 H18B 108.3 . . ? F2 C19 C17 108.25(15) . . ? F2 C19 H19A 110.0 . . ? C17 C19 H19A 110.0 . . ? F2 C19 H19B 110.0 . . ? C17 C19 H19B 110.0 . . ? H19A C19 H19B 108.4 . . ? O5 C20 O6 125.01(18) . . ? O5 C20 C17 123.21(18) . . ? O6 C20 C17 111.66(16) . . ? O6 C21 H21A 109.5 . . ? O6 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O6 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1 N1 H1A 108.7(17) . . ? C1 N1 H1B 107.7(17) . . ? H1A N1 H1B 109(2) . . ? C4 N2 C5 122.63(15) . . ? C8 N3 C9 121.97(15) . . ? C12 N4 C13 122.96(15) . . ? C16 N5 C17 121.07(15) . . ? C20 O6 C21 114.49(17) . . ? C22 Cl1 C22 32.1(3) . 2_756 ? C22 Cl2 C22 32.6(3) . 2_756 ? Cl1 C22 Cl2 114.3(3) . . ? Cl1 C22 Cl1 112.5(3) . 2_756 ? Cl2 C22 Cl1 111.1(3) . 2_756 ? Cl1 C22 H22 106.1 . . ? Cl2 C22 H22 106.1 . . ? Cl1 C22 H22 106.1 2_756 . ? 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 N1 C1 C4 O1 -179.04(17) . . . . ? C2 C1 C4 O1 -59.3(2) . . . . ? C3 C1 C4 O1 59.1(2) . . . . ? N1 C1 C4 N2 -0.2(2) . . . . ? C2 C1 C4 N2 119.51(17) . . . . ? C3 C1 C4 N2 -122.01(18) . . . . ? N2 C5 C8 O2 -130.85(17) . . . . ? C7 C5 C8 O2 -9.4(2) . . . . ? C6 C5 C8 O2 111.62(18) . . . . ? N2 C5 C8 N3 50.4(2) . . . . ? C7 C5 C8 N3 171.88(15) . . . . ? C6 C5 C8 N3 -67.1(2) . . . . ? N3 C9 C12 O3 -157.72(16) . . . . ? C10 C9 C12 O3 -34.2(2) . . . . ? C11 C9 C12 O3 85.7(2) . . . . ? N3 C9 C12 N4 27.0(2) . . . . ? C10 C9 C12 N4 150.48(16) . . . . ? C11 C9 C12 N4 -89.59(18) . . . . ? N4 C13 C16 O4 -159.63(16) . . . . ? C15 C13 C16 O4 -34.3(2) . . . . ? C14 C13 C16 O4 83.7(2) . . . . ? N4 C13 C16 N5 26.1(2) . . . . ? C15 C13 C16 N5 151.45(16) . . . . ? C14 C13 C16 N5 -90.55(18) . . . . ? N5 C17 C18 F1 178.45(14) . . . . ? C19 C17 C18 F1 -60.85(19) . . . . ? C20 C17 C18 F1 57.19(19) . . . . ? N5 C17 C19 F2 57.51(19) . . . . ? C18 C17 C19 F2 -59.77(19) . . . . ? C20 C17 C19 F2 -179.07(14) . . . . ? N5 C17 C20 O5 132.59(19) . . . . ? C19 C17 C20 O5 9.9(2) . . . . ? C18 C17 C20 O5 -110.4(2) . . . . ? N5 C17 C20 O6 -51.2(2) . . . . ? C19 C17 C20 O6 -173.94(15) . . . . ? C18 C17 C20 O6 65.78(19) . . . . ? O1 C4 N2 C5 -6.3(3) . . . . ? C1 C4 N2 C5 174.90(15) . . . . ? C7 C5 N2 C4 -72.2(2) . . . . ? C6 C5 N2 C4 166.93(16) . . . . ? C8 C5 N2 C4 48.4(2) . . . . ? O2 C8 N3 C9 -8.5(3) . . . . ? C5 C8 N3 C9 170.30(15) . . . . ? C10 C9 N3 C8 -62.5(2) . . . . ? C11 C9 N3 C8 176.84(16) . . . . ? C12 C9 N3 C8 60.6(2) . . . . ? O3 C12 N4 C13 4.5(3) . . . . ? C9 C12 N4 C13 179.62(15) . . . . ? C15 C13 N4 C12 -57.2(2) . . . . ? C14 C13 N4 C12 -177.18(15) . . . . ? C16 C13 N4 C12 67.1(2) . . . . ? O4 C16 N5 C17 3.3(3) . . . . ? C13 C16 N5 C17 177.48(15) . . . . ? C19 C17 N5 C16 78.4(2) . . . . ? C18 C17 N5 C16 -161.17(16) . . . . ? C20 C17 N5 C16 -42.0(2) . . . . ? O5 C20 O6 C21 -5.8(3) . . . . ? C17 C20 O6 C21 178.15(16) . . . . ? C22 Cl1 C22 Cl2 -65.5(3) 2_756 . . . ? C22 Cl1 C22 Cl1 62.3(4) 2_756 . . 2_756 ? C22 Cl2 C22 Cl1 67.9(5) 2_756 . . . ? C22 Cl2 C22 Cl1 -60.7(5) 2_756 . . 2_756 ? 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 N1 H1B O5 0.92(2) 2.41(2) 3.271(2) 156(2) 1_545 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 66.60 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.025 _refine_diff_density_min -1.067 _refine_diff_density_rms 0.082 data_s3600n _database_code_depnum_ccdc_archive 'CCDC 927332' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C47 H58 N6 O8' _chemical_formula_weight 834.99 _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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 13.0719(16) _cell_length_b 11.4964(14) _cell_length_c 15.273(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.562(3) _cell_angle_gamma 90.00 _cell_volume 2240.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 981 _cell_measurement_theta_min 2.237 _cell_measurement_theta_max 18.8145 _exptl_crystal_description plate _exptl_crystal_colour white _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 892 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 14252 _diffrn_reflns_av_R_equivalents 0.0938 _diffrn_reflns_av_sigmaI/netI 0.1896 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5497 _reflns_number_gt 2831 _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^)+(0.0000P)^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_abs_structure_Flack -0.1(12) _refine_ls_number_reflns 5497 _refine_ls_number_parameters 559 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1104 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.0763 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 0.691 _refine_ls_restrained_S_all 0.691 _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 -0.1227(3) 0.7482(4) 0.2146(3) 0.0187(10) Uani 1 1 d . . . C2 C -0.1975(3) 0.6643(4) 0.1791(3) 0.0283(12) Uani 1 1 d . . . H2 H -0.1845 0.6113 0.1351 0.034 Uiso 1 1 calc R . . C3 C -0.2903(3) 0.6585(4) 0.2080(3) 0.0341(13) Uani 1 1 d . . . H3 H -0.3417 0.6028 0.1823 0.041 Uiso 1 1 calc R . . C4 C -0.3095(3) 0.7317(4) 0.2731(3) 0.0331(13) Uani 1 1 d . . . H4 H -0.3735 0.7266 0.2927 0.040 Uiso 1 1 calc R . . C5 C -0.2345(3) 0.8135(4) 0.3102(3) 0.0283(12) Uani 1 1 d . . . H5 H -0.2467 0.8646 0.3557 0.034 Uiso 1 1 calc R . . C6 C -0.1425(3) 0.8202(4) 0.2808(3) 0.0243(11) Uani 1 1 d . . . H6 H -0.0913 0.8761 0.3068 0.029 Uiso 1 1 calc R . . C7 C -0.0251(3) 0.7601(4) 0.1771(3) 0.0248(11) Uani 1 1 d . . . H7A H -0.0122 0.6863 0.1480 0.030 Uiso 1 1 calc R . . H7B H -0.0360 0.8221 0.1310 0.030 Uiso 1 1 calc R . . C8 C 0.1186(3) 0.6966(4) 0.2906(3) 0.0172(10) Uani 1 1 d . . . C9 C 0.2596(3) 0.6553(3) 0.4205(3) 0.0171(10) Uani 1 1 d . . . H9 H 0.3237 0.6984 0.4517 0.021 Uiso 1 1 calc R . . C10 C 0.1995(3) 0.6229(3) 0.4916(3) 0.0210(11) Uani 1 1 d . . . H10A H 0.2442 0.5734 0.5376 0.025 Uiso 1 1 calc R . . H10B H 0.1366 0.5773 0.4636 0.025 Uiso 1 1 calc R . . C11 C 0.1661(3) 0.7301(3) 0.5363(3) 0.0204(10) Uani 1 1 d . . . C12 C 0.0640(3) 0.7682(4) 0.5159(3) 0.0303(12) Uani 1 1 d . . . H12 H 0.0132 0.7270 0.4731 0.036 Uiso 1 1 calc R . . C13 C 0.0340(4) 0.8672(4) 0.5574(3) 0.0340(13) Uani 1 1 d . . . H13 H -0.0370 0.8921 0.5430 0.041 Uiso 1 1 calc R . . C14 C 0.1055(4) 0.9280(4) 0.6182(3) 0.0309(12) Uani 1 1 d . . . H14 H 0.0848 0.9947 0.6467 0.037 Uiso 1 1 calc R . . C15 C 0.2084(4) 0.8918(4) 0.6378(3) 0.0383(14) Uani 1 1 d . . . H15 H 0.2593 0.9347 0.6793 0.046 Uiso 1 1 calc R . . C16 C 0.2379(4) 0.7937(4) 0.5978(3) 0.0333(12) Uani 1 1 d . . . H16 H 0.3090 0.7692 0.6128 0.040 Uiso 1 1 calc R . . C17 C 0.2976(3) 0.5481(4) 0.3754(3) 0.0165(10) Uani 1 1 d . . . C18 C 0.3985(3) 0.4842(4) 0.2644(3) 0.0167(10) Uani 1 1 d . . . C19 C 0.4274(3) 0.5383(3) 0.1816(3) 0.0222(11) Uani 1 1 d . . . H19A H 0.3633 0.5580 0.1376 0.033 Uiso 1 1 calc R . . H19B H 0.4687 0.4826 0.1551 0.033 Uiso 1 1 calc R . . H19C H 0.4687 0.6090 0.1990 0.033 Uiso 1 1 calc R . . C20 C 0.4967(3) 0.4384(4) 0.3291(3) 0.0257(11) Uani 1 1 d . . . H20A H 0.5439 0.5034 0.3508 0.039 Uiso 1 1 calc R . . H20B H 0.5326 0.3825 0.2977 0.039 Uiso 1 1 calc R . . H20C H 0.4765 0.3999 0.3800 0.039 Uiso 1 1 calc R . . C21 C 0.3255(3) 0.3815(4) 0.2299(3) 0.0183(10) Uani 1 1 d . . . C22 C 0.1481(3) 0.3125(4) 0.1627(3) 0.0215(11) Uani 1 1 d . . . C23 C 0.0379(3) 0.3570(3) 0.1603(3) 0.0307(13) Uani 1 1 d . . . H23A H 0.0316 0.3776 0.2211 0.046 Uiso 1 1 calc R . . H23B H -0.0131 0.2961 0.1365 0.046 Uiso 1 1 calc R . . H23C H 0.0242 0.4258 0.1217 0.046 Uiso 1 1 calc R . . C24 C 0.1624(3) 0.2829(4) 0.0696(3) 0.0310(12) Uani 1 1 d . . . H24A H 0.1462 0.3513 0.0308 0.046 Uiso 1 1 calc R . . H24B H 0.1151 0.2191 0.0450 0.046 Uiso 1 1 calc R . . H24C H 0.2351 0.2590 0.0728 0.046 Uiso 1 1 calc R . . C25 C 0.1669(3) 0.2035(4) 0.2238(3) 0.0183(10) Uani 1 1 d . . . C26 C 0.1952(3) 0.1343(3) 0.3817(3) 0.0173(10) Uani 1 1 d . . . C27 C 0.2255(3) 0.1919(3) 0.4743(2) 0.0245(11) Uani 1 1 d . . . H27A H 0.2928 0.2320 0.4801 0.037 Uiso 1 1 calc R . . H27B H 0.2317 0.1323 0.5210 0.037 Uiso 1 1 calc R . . H27C H 0.1715 0.2483 0.4809 0.037 Uiso 1 1 calc R . . C28 C 0.0906(3) 0.0694(4) 0.3703(3) 0.0253(11) Uani 1 1 d . . . H28A H 0.0341 0.1253 0.3708 0.038 Uiso 1 1 calc R . . H28B H 0.0944 0.0140 0.4197 0.038 Uiso 1 1 calc R . . H28C H 0.0763 0.0273 0.3131 0.038 Uiso 1 1 calc R . . C29 C 0.2824(3) 0.0468(4) 0.3777(3) 0.0156(10) Uani 1 1 d . . . C30 C 0.4456(3) -0.0004(3) 0.3326(3) 0.0169(10) Uani 1 1 d . . . C31 C 0.5155(3) 0.0594(4) 0.2771(3) 0.0226(11) Uani 1 1 d . . . H31A H 0.4728 0.0823 0.2186 0.034 Uiso 1 1 calc R . . H31B H 0.5704 0.0055 0.2683 0.034 Uiso 1 1 calc R . . H31C H 0.5478 0.1287 0.3090 0.034 Uiso 1 1 calc R . . C32 C 0.5112(3) -0.0374(4) 0.4237(3) 0.0260(11) Uani 1 1 d . . . H32A H 0.5424 0.0315 0.4568 0.039 Uiso 1 1 calc R . . H32B H 0.5669 -0.0902 0.4148 0.039 Uiso 1 1 calc R . . H32C H 0.4663 -0.0773 0.4578 0.039 Uiso 1 1 calc R . . C33 C 0.3962(3) -0.1066(4) 0.2776(3) 0.0181(10) Uani 1 1 d . . . C34 C 0.2626(3) -0.1702(3) 0.1480(2) 0.0178(10) Uani 1 1 d . . . H34A H 0.1918 -0.1899 0.1566 0.021 Uiso 1 1 calc R . . H34B H 0.3051 -0.2422 0.1558 0.021 Uiso 1 1 calc R . . C35 C 0.2541(3) -0.1239(4) 0.0531(3) 0.0212(11) Uani 1 1 d . . . C36 C 0.3591(3) -0.0710(4) 0.0470(3) 0.0212(11) Uani 1 1 d . . . C37 C 0.4497(3) -0.1371(4) 0.0669(3) 0.0259(12) Uani 1 1 d . . . H37 H 0.4446 -0.2172 0.0808 0.031 Uiso 1 1 calc R . . C38 C 0.5476(4) -0.0904(4) 0.0671(3) 0.0344(13) Uani 1 1 d . . . H38 H 0.6084 -0.1380 0.0804 0.041 Uiso 1 1 calc R . . C39 C 0.5556(4) 0.0265(5) 0.0477(3) 0.0391(14) Uani 1 1 d . . . H39 H 0.6221 0.0600 0.0481 0.047 Uiso 1 1 calc R . . C40 C 0.4662(4) 0.0941(4) 0.0277(3) 0.0418(14) Uani 1 1 d . . . H40 H 0.4712 0.1742 0.0139 0.050 Uiso 1 1 calc R . . C41 C 0.3695(4) 0.0457(4) 0.0277(3) 0.0310(12) Uani 1 1 d . . . H41 H 0.3087 0.0935 0.0142 0.037 Uiso 1 1 calc R . . C42 C 0.2205(3) -0.2217(4) -0.0159(3) 0.0194(10) Uani 1 1 d . . . C43 C 0.2441(3) -0.2136(4) -0.0991(3) 0.0337(12) Uani 1 1 d . . . H43 H 0.2838 -0.1492 -0.1122 0.040 Uiso 1 1 calc R . . C44 C 0.2110(4) -0.2979(5) -0.1644(3) 0.0431(14) Uani 1 1 d . . . H44 H 0.2278 -0.2911 -0.2217 0.052 Uiso 1 1 calc R . . C45 C 0.1534(4) -0.3922(4) -0.1452(3) 0.0417(15) Uani 1 1 d . . . H45 H 0.1314 -0.4509 -0.1890 0.050 Uiso 1 1 calc R . . C46 C 0.1281(4) -0.4007(4) -0.0629(3) 0.0394(14) Uani 1 1 d . . . H46 H 0.0871 -0.4640 -0.0501 0.047 Uiso 1 1 calc R . . C47 C 0.1628(3) -0.3162(4) 0.0014(3) 0.0307(12) Uani 1 1 d . . . H47 H 0.1465 -0.3235 0.0588 0.037 Uiso 1 1 calc R . . N1 N 0.2006(2) 0.7337(3) 0.3532(2) 0.0149(8) Uani 1 1 d . . . H1 H 0.2193 0.8072 0.3536 0.018 Uiso 1 1 calc R . . N2 N 0.3458(2) 0.5714(3) 0.3077(2) 0.0157(8) Uani 1 1 d . . . H2A H 0.3453 0.6436 0.2886 0.019 Uiso 1 1 calc R . . N3 N 0.2227(2) 0.4040(3) 0.2030(2) 0.0176(8) Uani 1 1 d . . . H3A H 0.1993 0.4745 0.2095 0.021 Uiso 1 1 calc R . . N4 N 0.1875(2) 0.2245(3) 0.3127(2) 0.0166(8) Uani 1 1 d . . . H4A H 0.1971 0.2972 0.3306 0.020 Uiso 1 1 calc R . . N5 N 0.3627(2) 0.0806(3) 0.3422(2) 0.0172(8) Uani 1 1 d . . . H5A H 0.3656 0.1531 0.3243 0.021 Uiso 1 1 calc R . . N6 N 0.3101(2) -0.0862(3) 0.2148(2) 0.0182(9) Uani 1 1 d . . . H6A H 0.2804 -0.0174 0.2140 0.022 Uiso 1 1 calc R . . O1 O 0.0651(2) 0.7882(2) 0.24667(17) 0.0213(7) Uani 1 1 d . . . O2 O 0.0950(2) 0.5951(2) 0.27274(18) 0.0224(7) Uani 1 1 d . . . O3 O 0.2836(2) 0.4478(2) 0.40106(17) 0.0185(7) Uani 1 1 d . . . O4 O 0.3623(2) 0.2840(2) 0.22155(17) 0.0202(7) Uani 1 1 d . . . O5 O 0.1587(2) 0.1043(2) 0.19216(18) 0.0193(7) Uani 1 1 d . . . O6 O 0.2804(2) -0.0508(2) 0.41115(18) 0.0221(7) Uani 1 1 d . . . O7 O 0.4394(2) -0.2041(2) 0.28941(17) 0.0207(7) Uani 1 1 d . . . O8 O 0.1706(2) -0.0394(3) 0.03198(18) 0.0277(8) Uani 1 1 d . . . H8 H 0.1713 0.0029 0.0770 0.042 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 C1 0.020(2) 0.020(3) 0.016(2) 0.0058(19) 0.0021(19) 0.004(2) C2 0.021(3) 0.032(3) 0.030(3) -0.005(2) 0.003(2) 0.001(2) C3 0.026(3) 0.036(3) 0.039(3) 0.000(3) 0.002(2) -0.003(2) C4 0.015(3) 0.044(4) 0.039(3) 0.014(3) 0.005(2) 0.004(3) C5 0.028(3) 0.028(3) 0.030(3) 0.008(2) 0.009(2) 0.008(2) C6 0.016(2) 0.024(3) 0.030(3) 0.009(2) -0.001(2) -0.007(2) C7 0.018(2) 0.037(3) 0.017(2) 0.008(2) -0.0013(19) 0.004(2) C8 0.010(2) 0.026(3) 0.018(2) 0.000(2) 0.0091(18) 0.005(2) C9 0.016(2) 0.017(2) 0.020(2) -0.003(2) 0.0072(19) -0.001(2) C10 0.020(3) 0.020(3) 0.023(3) -0.003(2) 0.005(2) 0.004(2) C11 0.028(3) 0.012(3) 0.024(3) 0.008(2) 0.012(2) 0.001(2) C12 0.027(3) 0.026(3) 0.041(3) -0.001(2) 0.013(2) -0.009(2) C13 0.024(3) 0.022(3) 0.061(4) 0.005(3) 0.019(3) 0.008(2) C14 0.039(3) 0.023(3) 0.037(3) -0.003(2) 0.024(2) 0.006(3) C15 0.046(3) 0.035(3) 0.032(3) -0.017(3) 0.007(3) 0.003(3) C16 0.031(3) 0.038(3) 0.029(3) -0.004(3) 0.005(2) 0.013(3) C17 0.015(2) 0.016(3) 0.015(2) -0.001(2) -0.0040(18) -0.001(2) C18 0.016(2) 0.016(3) 0.019(3) -0.001(2) 0.0061(19) 0.006(2) C19 0.022(3) 0.017(3) 0.030(3) 0.000(2) 0.011(2) 0.000(2) C20 0.024(3) 0.023(3) 0.028(3) -0.007(2) 0.002(2) 0.009(2) C21 0.023(3) 0.017(3) 0.015(2) 0.005(2) 0.0044(19) 0.002(2) C22 0.025(3) 0.011(3) 0.023(3) -0.003(2) -0.009(2) -0.001(2) C23 0.027(3) 0.010(3) 0.047(3) -0.006(2) -0.010(2) -0.001(2) C24 0.052(3) 0.016(3) 0.020(3) 0.004(2) -0.003(2) -0.001(2) C25 0.012(2) 0.019(3) 0.020(2) 0.004(2) -0.0030(18) 0.003(2) C26 0.023(3) 0.016(3) 0.015(2) -0.001(2) 0.0069(19) -0.005(2) C27 0.036(3) 0.014(3) 0.025(3) 0.003(2) 0.009(2) -0.002(2) C28 0.024(3) 0.016(3) 0.036(3) -0.001(2) 0.007(2) -0.002(2) C29 0.019(2) 0.014(2) 0.014(2) -0.0030(19) 0.0026(18) -0.004(2) C30 0.015(2) 0.018(3) 0.017(2) -0.0028(19) 0.0024(19) -0.001(2) C31 0.017(2) 0.021(3) 0.030(3) 0.002(2) 0.006(2) -0.001(2) C32 0.027(3) 0.018(3) 0.030(3) -0.003(2) -0.001(2) 0.003(2) C33 0.018(2) 0.020(3) 0.017(2) 0.001(2) 0.0045(19) -0.003(2) C34 0.020(2) 0.017(2) 0.017(2) -0.0047(19) 0.0060(19) -0.002(2) C35 0.018(2) 0.021(3) 0.024(3) -0.004(2) 0.002(2) 0.003(2) C36 0.028(3) 0.017(3) 0.021(3) -0.003(2) 0.011(2) 0.001(2) C37 0.027(3) 0.022(3) 0.030(3) 0.000(2) 0.009(2) -0.004(2) C38 0.027(3) 0.041(3) 0.037(3) -0.005(3) 0.011(2) -0.005(3) C39 0.041(3) 0.043(4) 0.037(3) -0.010(3) 0.016(3) -0.029(3) C40 0.057(4) 0.024(3) 0.048(4) 0.006(3) 0.020(3) -0.011(3) C41 0.044(3) 0.023(3) 0.027(3) 0.005(2) 0.009(2) -0.008(3) C42 0.017(2) 0.019(3) 0.020(2) -0.001(2) -0.0003(19) 0.008(2) C43 0.035(3) 0.036(3) 0.031(3) -0.009(3) 0.009(2) 0.004(3) C44 0.053(4) 0.051(4) 0.026(3) -0.016(3) 0.008(3) 0.012(3) C45 0.053(4) 0.023(3) 0.040(4) -0.017(3) -0.010(3) 0.006(3) C46 0.055(4) 0.013(3) 0.040(3) 0.002(3) -0.013(3) 0.000(3) C47 0.038(3) 0.029(3) 0.020(3) -0.002(2) -0.005(2) -0.002(3) N1 0.0145(19) 0.0084(19) 0.022(2) 0.0043(16) 0.0055(15) -0.0027(16) N2 0.021(2) 0.008(2) 0.018(2) 0.0047(16) 0.0054(16) 0.0023(16) N3 0.019(2) 0.0073(19) 0.026(2) 0.0029(16) 0.0043(16) 0.0029(16) N4 0.018(2) 0.009(2) 0.021(2) -0.0020(16) 0.0014(16) -0.0028(16) N5 0.021(2) 0.007(2) 0.023(2) -0.0025(16) 0.0033(16) -0.0028(16) N6 0.019(2) 0.016(2) 0.019(2) -0.0031(17) 0.0023(16) 0.0011(17) O1 0.0181(16) 0.0159(17) 0.0294(17) 0.0038(15) 0.0040(13) 0.0008(14) O2 0.0190(17) 0.0123(17) 0.034(2) -0.0049(14) 0.0024(14) -0.0039(14) O3 0.0220(17) 0.0102(17) 0.0230(17) 0.0017(14) 0.0040(13) -0.0013(14) O4 0.0228(17) 0.0108(17) 0.0287(18) 0.0027(15) 0.0091(13) 0.0070(14) O5 0.0219(17) 0.0101(16) 0.0242(18) -0.0044(14) 0.0013(13) -0.0002(14) O6 0.0335(19) 0.0106(17) 0.0220(17) 0.0007(14) 0.0054(14) -0.0061(15) O7 0.0181(16) 0.0108(16) 0.0339(18) 0.0028(15) 0.0071(13) 0.0015(14) O8 0.0328(18) 0.0219(19) 0.0245(19) -0.0077(15) -0.0024(15) 0.0099(16) _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 C6 1.374(5) . ? C1 C2 1.395(5) . ? C1 C7 1.514(5) . ? C2 C3 1.380(5) . ? C2 H2 0.9500 . ? C3 C4 1.365(6) . ? C3 H3 0.9500 . ? C4 C5 1.387(5) . ? C4 H4 0.9500 . ? C5 C6 1.375(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.441(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O2 1.223(5) . ? C8 N1 1.342(4) . ? C8 O1 1.357(4) . ? C9 N1 1.455(4) . ? C9 C10 1.520(5) . ? C9 C17 1.545(5) . ? C9 H9 1.0000 . ? C10 C11 1.518(5) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.376(5) . ? C11 C16 1.383(5) . ? C12 C13 1.400(5) . ? C12 H12 0.9500 . ? C13 C14 1.358(6) . ? C13 H13 0.9500 . ? C14 C15 1.377(6) . ? C14 H14 0.9500 . ? C15 C16 1.377(6) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 O3 1.245(4) . ? C17 N2 1.350(5) . ? C18 N2 1.453(4) . ? C18 C19 1.529(5) . ? C18 C20 1.533(5) . ? C18 C21 1.537(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 O4 1.237(4) . ? C21 N3 1.342(5) . ? C22 N3 1.474(5) . ? C22 C24 1.512(5) . ? C22 C23 1.522(5) . ? C22 C25 1.550(5) . ? 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 O5 1.234(5) . ? C25 N4 1.348(5) . ? C26 N4 1.466(5) . ? C26 C28 1.534(5) . ? C26 C29 1.531(5) . ? C26 C27 1.534(5) . ? 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 O6 1.236(4) . ? C29 N5 1.340(5) . ? C30 N5 1.460(5) . ? C30 C32 1.528(5) . ? C30 C31 1.537(5) . ? C30 C33 1.542(5) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 O7 1.250(4) . ? C33 N6 1.331(5) . ? C34 N6 1.444(4) . ? C34 C35 1.525(5) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 O8 1.444(4) . ? C35 C36 1.522(6) . ? C35 C42 1.538(5) . ? C36 C37 1.384(5) . ? C36 C41 1.387(5) . ? C37 C38 1.387(6) . ? C37 H37 0.9500 . ? C38 C39 1.386(6) . ? C38 H38 0.9500 . ? C39 C40 1.381(6) . ? C39 H39 0.9500 . ? C40 C41 1.381(6) . ? C40 H40 0.9500 . ? C41 H41 0.9500 . ? C42 C43 1.375(5) . ? C42 C47 1.381(6) . ? C43 C44 1.391(6) . ? C43 H43 0.9500 . ? C44 C45 1.388(6) . ? C44 H44 0.9500 . ? C45 C46 1.370(6) . ? C45 H45 0.9500 . ? C46 C47 1.386(6) . ? C46 H46 0.9500 . ? C47 H47 0.9500 . ? N1 H1 0.8800 . ? N2 H2A 0.8800 . ? N3 H3A 0.8800 . ? N4 H4A 0.8800 . ? N5 H5A 0.8800 . ? N6 H6A 0.8800 . ? O8 H8 0.8400 . ? 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 C6 C1 C2 118.3(4) . . ? C6 C1 C7 122.1(4) . . ? C2 C1 C7 119.5(4) . . ? C3 C2 C1 120.0(4) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C4 C3 C2 121.1(5) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 119.3(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 119.6(4) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C1 C6 C5 121.6(4) . . ? C1 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? O1 C7 C1 111.3(3) . . ? O1 C7 H7A 109.4 . . ? C1 C7 H7A 109.4 . . ? O1 C7 H7B 109.4 . . ? C1 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O2 C8 N1 125.8(4) . . ? O2 C8 O1 123.5(4) . . ? N1 C8 O1 110.6(4) . . ? N1 C9 C10 112.3(3) . . ? N1 C9 C17 110.6(3) . . ? C10 C9 C17 112.9(3) . . ? N1 C9 H9 106.9 . . ? C10 C9 H9 106.9 . . ? C17 C9 H9 106.9 . . ? C9 C10 C11 111.5(3) . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10B 109.3 . . ? C11 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C16 117.9(4) . . ? C12 C11 C10 121.1(4) . . ? C16 C11 C10 121.0(4) . . ? C11 C12 C13 120.7(4) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.6(4) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.2(4) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? C16 C15 C14 120.4(5) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 121.3(4) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? O3 C17 N2 123.3(4) . . ? O3 C17 C9 121.0(4) . . ? N2 C17 C9 115.6(4) . . ? N2 C18 C19 108.8(3) . . ? N2 C18 C20 110.9(3) . . ? C19 C18 C20 110.5(3) . . ? N2 C18 C21 111.4(3) . . ? C19 C18 C21 106.0(3) . . ? C20 C18 C21 109.1(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O4 C21 N3 121.9(4) . . ? O4 C21 C18 120.3(4) . . ? N3 C21 C18 117.6(4) . . ? N3 C22 C24 110.4(4) . . ? N3 C22 C23 107.9(3) . . ? C24 C22 C23 111.3(3) . . ? N3 C22 C25 108.8(3) . . ? C24 C22 C25 110.4(4) . . ? C23 C22 C25 108.1(4) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O5 C25 N4 122.8(4) . . ? O5 C25 C22 121.5(4) . . ? N4 C25 C22 115.6(4) . . ? N4 C26 C28 110.1(3) . . ? N4 C26 C29 111.8(3) . . ? C28 C26 C29 109.2(3) . . ? N4 C26 C27 108.7(3) . . ? C28 C26 C27 111.1(3) . . ? C29 C26 C27 105.9(3) . . ? 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 . . ? O6 C29 N5 121.3(4) . . ? O6 C29 C26 119.8(4) . . ? N5 C29 C26 118.8(4) . . ? N5 C30 C32 111.6(3) . . ? N5 C30 C31 108.2(3) . . ? C32 C30 C31 110.1(3) . . ? N5 C30 C33 109.2(3) . . ? C32 C30 C33 111.2(3) . . ? C31 C30 C33 106.4(3) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C30 C32 H32A 109.5 . . ? C30 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C30 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O7 C33 N6 123.2(4) . . ? O7 C33 C30 120.6(3) . . ? N6 C33 C30 116.1(4) . . ? N6 C34 C35 111.7(3) . . ? N6 C34 H34A 109.3 . . ? C35 C34 H34A 109.3 . . ? N6 C34 H34B 109.3 . . ? C35 C34 H34B 109.3 . . ? H34A C34 H34B 107.9 . . ? O8 C35 C34 110.0(3) . . ? O8 C35 C36 111.4(3) . . ? C34 C35 C36 108.5(3) . . ? O8 C35 C42 104.4(3) . . ? C34 C35 C42 110.3(3) . . ? C36 C35 C42 112.2(4) . . ? C37 C36 C41 117.4(4) . . ? C37 C36 C35 120.4(4) . . ? C41 C36 C35 122.0(4) . . ? C36 C37 C38 122.2(4) . . ? C36 C37 H37 118.9 . . ? C38 C37 H37 118.9 . . ? C37 C38 C39 119.2(5) . . ? C37 C38 H38 120.4 . . ? C39 C38 H38 120.4 . . ? C40 C39 C38 119.6(5) . . ? C40 C39 H39 120.2 . . ? C38 C39 H39 120.2 . . ? C39 C40 C41 120.3(5) . . ? C39 C40 H40 119.9 . . ? C41 C40 H40 119.9 . . ? C40 C41 C36 121.4(5) . . ? C40 C41 H41 119.3 . . ? C36 C41 H41 119.3 . . ? C43 C42 C47 118.2(4) . . ? C43 C42 C35 119.7(4) . . ? C47 C42 C35 122.1(4) . . ? C42 C43 C44 121.2(5) . . ? C42 C43 H43 119.4 . . ? C44 C43 H43 119.4 . . ? C43 C44 C45 119.4(5) . . ? C43 C44 H44 120.3 . . ? C45 C44 H44 120.3 . . ? C46 C45 C44 120.0(5) . . ? C46 C45 H45 120.0 . . ? C44 C45 H45 120.0 . . ? C45 C46 C47 119.6(5) . . ? C45 C46 H46 120.2 . . ? C47 C46 H46 120.2 . . ? C42 C47 C46 121.6(5) . . ? C42 C47 H47 119.2 . . ? C46 C47 H47 119.2 . . ? C8 N1 C9 121.7(3) . . ? C8 N1 H1 119.1 . . ? C9 N1 H1 119.1 . . ? C17 N2 C18 124.0(3) . . ? C17 N2 H2A 118.0 . . ? C18 N2 H2A 118.0 . . ? C21 N3 C22 121.2(3) . . ? C21 N3 H3A 119.4 . . ? C22 N3 H3A 119.4 . . ? C25 N4 C26 124.4(4) . . ? C25 N4 H4A 117.8 . . ? C26 N4 H4A 117.8 . . ? C29 N5 C30 121.3(3) . . ? C29 N5 H5A 119.3 . . ? C30 N5 H5A 119.3 . . ? C33 N6 C34 123.9(4) . . ? C33 N6 H6A 118.1 . . ? C34 N6 H6A 118.1 . . ? C8 O1 C7 116.2(3) . . ? C35 O8 H8 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 C6 C1 C2 C3 2.6(6) . . . . ? C7 C1 C2 C3 -175.1(4) . . . . ? C1 C2 C3 C4 -1.9(7) . . . . ? C2 C3 C4 C5 0.4(7) . . . . ? C3 C4 C5 C6 0.3(6) . . . . ? C2 C1 C6 C5 -1.9(6) . . . . ? C7 C1 C6 C5 175.7(4) . . . . ? C4 C5 C6 C1 0.5(6) . . . . ? C6 C1 C7 O1 38.7(5) . . . . ? C2 C1 C7 O1 -143.7(4) . . . . ? N1 C9 C10 C11 -55.8(4) . . . . ? C17 C9 C10 C11 178.4(3) . . . . ? C9 C10 C11 C12 104.4(4) . . . . ? C9 C10 C11 C16 -74.5(5) . . . . ? C16 C11 C12 C13 -1.0(6) . . . . ? C10 C11 C12 C13 180.0(4) . . . . ? C11 C12 C13 C14 0.6(7) . . . . ? C12 C13 C14 C15 0.6(7) . . . . ? C13 C14 C15 C16 -1.3(7) . . . . ? C14 C15 C16 C11 0.9(8) . . . . ? C12 C11 C16 C15 0.3(7) . . . . ? C10 C11 C16 C15 179.3(4) . . . . ? N1 C9 C17 O3 -130.7(4) . . . . ? C10 C9 C17 O3 -3.9(5) . . . . ? N1 C9 C17 N2 49.2(4) . . . . ? C10 C9 C17 N2 176.0(3) . . . . ? N2 C18 C21 O4 -153.7(4) . . . . ? C19 C18 C21 O4 88.1(4) . . . . ? C20 C18 C21 O4 -30.9(5) . . . . ? N2 C18 C21 N3 31.5(5) . . . . ? C19 C18 C21 N3 -86.8(4) . . . . ? C20 C18 C21 N3 154.3(3) . . . . ? N3 C22 C25 O5 -143.3(4) . . . . ? C24 C22 C25 O5 -22.1(5) . . . . ? C23 C22 C25 O5 99.8(4) . . . . ? N3 C22 C25 N4 39.6(5) . . . . ? C24 C22 C25 N4 160.9(3) . . . . ? C23 C22 C25 N4 -77.3(4) . . . . ? N4 C26 C29 O6 -158.7(3) . . . . ? C28 C26 C29 O6 -36.7(5) . . . . ? C27 C26 C29 O6 83.1(4) . . . . ? N4 C26 C29 N5 25.0(5) . . . . ? C28 C26 C29 N5 147.0(4) . . . . ? C27 C26 C29 N5 -93.2(4) . . . . ? N5 C30 C33 O7 -151.1(4) . . . . ? C32 C30 C33 O7 -27.6(5) . . . . ? C31 C30 C33 O7 92.3(4) . . . . ? N5 C30 C33 N6 32.6(5) . . . . ? C32 C30 C33 N6 156.1(4) . . . . ? C31 C30 C33 N6 -84.0(4) . . . . ? N6 C34 C35 O8 -74.7(4) . . . . ? N6 C34 C35 C36 47.4(4) . . . . ? N6 C34 C35 C42 170.6(3) . . . . ? O8 C35 C36 C37 178.4(4) . . . . ? C34 C35 C36 C37 57.2(5) . . . . ? C42 C35 C36 C37 -64.8(5) . . . . ? O8 C35 C36 C41 2.9(6) . . . . ? C34 C35 C36 C41 -118.3(4) . . . . ? C42 C35 C36 C41 119.6(4) . . . . ? C41 C36 C37 C38 -0.5(6) . . . . ? C35 C36 C37 C38 -176.3(4) . . . . ? C36 C37 C38 C39 0.6(7) . . . . ? C37 C38 C39 C40 -0.6(7) . . . . ? C38 C39 C40 C41 0.5(7) . . . . ? C39 C40 C41 C36 -0.4(7) . . . . ? C37 C36 C41 C40 0.4(7) . . . . ? C35 C36 C41 C40 176.1(4) . . . . ? O8 C35 C42 C43 85.6(5) . . . . ? C34 C35 C42 C43 -156.3(4) . . . . ? C36 C35 C42 C43 -35.2(5) . . . . ? O8 C35 C42 C47 -91.5(4) . . . . ? C34 C35 C42 C47 26.6(5) . . . . ? C36 C35 C42 C47 147.6(4) . . . . ? C47 C42 C43 C44 0.0(6) . . . . ? C35 C42 C43 C44 -177.2(4) . . . . ? C42 C43 C44 C45 -0.2(7) . . . . ? C43 C44 C45 C46 1.0(7) . . . . ? C44 C45 C46 C47 -1.6(7) . . . . ? C43 C42 C47 C46 -0.7(6) . . . . ? C35 C42 C47 C46 176.5(4) . . . . ? C45 C46 C47 C42 1.5(7) . . . . ? O2 C8 N1 C9 -12.9(6) . . . . ? O1 C8 N1 C9 168.7(3) . . . . ? C10 C9 N1 C8 -73.4(5) . . . . ? C17 C9 N1 C8 53.8(5) . . . . ? O3 C17 N2 C18 -8.1(6) . . . . ? C9 C17 N2 C18 172.0(3) . . . . ? C19 C18 N2 C17 170.7(3) . . . . ? C20 C18 N2 C17 -67.6(5) . . . . ? C21 C18 N2 C17 54.2(5) . . . . ? O4 C21 N3 C22 0.6(6) . . . . ? C18 C21 N3 C22 175.3(3) . . . . ? C24 C22 N3 C21 -71.4(5) . . . . ? C23 C22 N3 C21 166.8(4) . . . . ? C25 C22 N3 C21 49.8(5) . . . . ? O5 C25 N4 C26 -4.6(6) . . . . ? C22 C25 N4 C26 172.4(3) . . . . ? C28 C26 N4 C25 -61.2(5) . . . . ? C29 C26 N4 C25 60.4(5) . . . . ? C27 C26 N4 C25 176.9(3) . . . . ? O6 C29 N5 C30 6.8(6) . . . . ? C26 C29 N5 C30 -177.0(3) . . . . ? C32 C30 N5 C29 -67.3(5) . . . . ? C31 C30 N5 C29 171.4(3) . . . . ? C33 C30 N5 C29 56.0(5) . . . . ? O7 C33 N6 C34 -6.2(6) . . . . ? C30 C33 N6 C34 170.0(4) . . . . ? C35 C34 N6 C33 -122.6(4) . . . . ? O2 C8 O1 C7 1.3(5) . . . . ? N1 C8 O1 C7 179.8(3) . . . . ? C1 C7 O1 C8 87.8(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 N1 H1 O6 0.88 1.94 2.758(4) 153.8 1_565 N2 H2A O7 0.88 2.14 2.896(4) 143.9 1_565 N3 H3A O2 0.88 2.30 3.086(4) 148.8 . N4 H4A O3 0.88 2.21 3.041(4) 156.4 . N5 H5A O4 0.88 2.17 2.976(4) 152.4 . N6 H6A O5 0.88 2.09 2.921(4) 157.2 . O8 H8 O5 0.84 2.15 2.984(4) 174.6 . _diffrn_measured_fraction_theta_max 0.939 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.185 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.045