# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Victor Maurizot' _publ_contact_author_email VICTOR.MAURIZOT@U-BORDEAUX2.FR _publ_section_title ; Cylindrical sheet formation of oligo-meta-aniline foldamers ; loop_ _publ_author_name 'Victor Maurizot' 'Gerard Deleris' 'Jean-Michel Leger' 'S. Massip' # Attachment 'cif-maurizot-revised.txt' # Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_vm114c _database_code_depnum_ccdc_archive 'CCDC 731795' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 N4 O6' _chemical_formula_weight 410.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x, -y+1/2, z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z-1/2' '-x, y-1/2, -z' 'x-1/2, y, -z-1/2' _cell_length_a 19.9110(18) _cell_length_b 23.1854(3) _cell_length_c 4.0727(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1880.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1306 _cell_measurement_theta_min 7.25 _cell_measurement_theta_max 72.14 _exptl_crystal_description 'needle recut' _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.920 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8743 _exptl_absorpt_correction_T_max 0.9300 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'micro-focus rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku RAXIS Rapid' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22971 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 7.25 _diffrn_reflns_theta_max 72.14 _reflns_number_total 1846 _reflns_number_gt 1306 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.2843P] 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 SHELXL _refine_ls_extinction_coef ? _refine_ls_number_reflns 1846 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1105 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.005 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 0.64957(9) 0.58321(8) 0.4661(5) 0.0535(5) Uani 1 1 d . . . C2 C 0.71154(11) 0.56621(9) 0.5828(5) 0.0678(6) Uani 1 1 d . . . H2 H 0.7158 0.5322 0.7022 0.081 Uiso 1 1 calc R . . C3 C 0.76724(11) 0.59995(11) 0.5212(6) 0.0772(7) Uani 1 1 d . . . H3 H 0.8089 0.5888 0.6029 0.093 Uiso 1 1 calc R . . C4 C 0.76191(10) 0.64947(10) 0.3415(6) 0.0742(7) Uani 1 1 d . . . H4 H 0.7999 0.6717 0.3008 0.089 Uiso 1 1 calc R . . C5 C 0.69997(9) 0.66662(9) 0.2196(6) 0.0629(6) Uani 1 1 d . . . H5 H 0.6966 0.6998 0.0926 0.075 Uiso 1 1 calc R . . C6 C 0.64326(8) 0.63435(8) 0.2868(5) 0.0505(5) Uani 1 1 d . . . O7 O 0.59122(7) 0.55338(5) 0.5060(4) 0.0654(4) Uani 1 1 d . . . C8 C 0.59272(13) 0.50017(9) 0.6825(6) 0.0795(7) Uani 1 1 d . . . H8A H 0.6234 0.4741 0.5776 0.119 Uiso 1 1 calc R . . H8B H 0.5486 0.4835 0.6847 0.119 Uiso 1 1 calc R . . H8C H 0.6072 0.5071 0.9039 0.119 Uiso 1 1 calc R . . N9 N 0.57888(7) 0.64616(6) 0.1600(4) 0.0544(5) Uani 1 1 d . . . H9 H 0.5535 0.6165 0.1365 0.065 Uiso 1 1 calc R . . C10 C 0.55065(8) 0.69687(7) 0.0690(5) 0.0438(4) Uani 1 1 d . . . C11 C 0.48982(8) 0.69829(7) -0.1155(4) 0.0448(5) Uani 1 1 d . . . C12 C 0.46137(12) 0.7500 -0.2029(6) 0.0479(6) Uani 1 2 d S . . H12 H 0.4218 0.7500 -0.3245 0.057 Uiso 1 2 calc SR . . C13 C 0.57853(11) 0.7500 0.1552(6) 0.0447(6) Uani 1 2 d S . . H13 H 0.6180 0.7500 0.2774 0.054 Uiso 1 2 calc SR . . N14 N 0.45432(7) 0.64718(7) -0.2181(4) 0.0549(5) Uani 1 1 d . . . O15 O 0.40962(7) 0.65166(6) -0.4235(4) 0.0812(5) Uani 1 1 d . . . O16 O 0.46901(7) 0.60029(6) -0.0949(4) 0.0714(5) 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 0.0635(11) 0.0454(10) 0.0517(13) -0.0052(9) 0.0009(10) 0.0093(9) C2 0.0777(14) 0.0613(12) 0.0645(16) -0.0045(11) -0.0101(11) 0.0224(11) C3 0.0605(12) 0.0832(17) 0.0881(18) -0.0190(14) -0.0137(12) 0.0208(12) C4 0.0491(11) 0.0762(16) 0.097(2) -0.0154(14) 0.0042(12) 0.0048(10) C5 0.0532(11) 0.0555(11) 0.0800(17) -0.0019(11) 0.0074(10) 0.0049(9) C6 0.0514(10) 0.0447(10) 0.0555(13) -0.0053(9) 0.0005(9) 0.0078(8) O7 0.0744(9) 0.0459(8) 0.0760(11) 0.0120(7) 0.0002(7) 0.0012(6) C8 0.1139(18) 0.0480(12) 0.0767(17) 0.0129(12) -0.0069(14) -0.0003(11) N9 0.0509(8) 0.0367(8) 0.0757(12) 0.0022(8) -0.0046(8) 0.0004(6) C10 0.0449(9) 0.0398(9) 0.0469(12) 0.0018(8) 0.0053(8) 0.0000(7) C11 0.0439(9) 0.0390(10) 0.0515(12) -0.0031(8) 0.0033(8) -0.0027(7) C12 0.0411(12) 0.0518(15) 0.0508(17) 0.000 0.0008(11) 0.000 C13 0.0437(12) 0.0411(13) 0.0495(17) 0.000 -0.0015(11) 0.000 N14 0.0487(8) 0.0481(10) 0.0679(13) -0.0053(8) 0.0033(8) -0.0081(7) O15 0.0710(9) 0.0720(10) 0.1007(14) -0.0050(9) -0.0301(9) -0.0143(7) O16 0.0719(9) 0.0427(8) 0.0997(13) 0.0012(8) -0.0061(8) -0.0084(6) _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 O7 1.362(2) . ? C1 C2 1.380(3) . ? C1 C6 1.398(3) . ? C2 C3 1.380(3) . ? C3 C4 1.365(3) . ? C4 C5 1.388(3) . ? C5 C6 1.382(2) . ? C6 N9 1.409(2) . ? O7 C8 1.428(2) . ? N9 C10 1.355(2) . ? C10 C13 1.396(2) . ? C10 C11 1.426(2) . ? C11 C12 1.373(2) . ? C11 N14 1.442(2) . ? C12 C11 1.373(2) 3_565 ? C13 C10 1.396(2) 3_565 ? N14 O15 1.226(2) . ? N14 O16 1.2324(19) . ? 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 O7 C1 C2 125.24(19) . . ? O7 C1 C6 114.59(16) . . ? C2 C1 C6 120.16(19) . . ? C1 C2 C3 119.6(2) . . ? C4 C3 C2 120.8(2) . . ? C3 C4 C5 120.1(2) . . ? C6 C5 C4 120.0(2) . . ? C5 C6 C1 119.29(17) . . ? C5 C6 N9 124.43(17) . . ? C1 C6 N9 115.99(16) . . ? C1 O7 C8 118.74(16) . . ? C10 N9 C6 130.27(15) . . ? N9 C10 C13 122.14(17) . . ? N9 C10 C11 121.10(15) . . ? C13 C10 C11 116.74(16) . . ? C12 C11 C10 120.48(16) . . ? C12 C11 N14 116.13(17) . . ? C10 C11 N14 123.38(15) . . ? C11 C12 C11 121.7(2) 3_565 . ? C10 C13 C10 123.9(2) . 3_565 ? O15 N14 O16 121.66(15) . . ? O15 N14 C11 118.94(16) . . ? O16 N14 C11 119.39(16) . . ? 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 O7 C1 C2 C3 178.9(2) . . . . ? C6 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C3 C4 C5 C6 1.6(3) . . . . ? C4 C5 C6 C1 -2.7(3) . . . . ? C4 C5 C6 N9 -176.25(19) . . . . ? O7 C1 C6 C5 -177.15(18) . . . . ? C2 C1 C6 C5 2.0(3) . . . . ? O7 C1 C6 N9 -3.1(3) . . . . ? C2 C1 C6 N9 176.02(18) . . . . ? C2 C1 O7 C8 0.2(3) . . . . ? C6 C1 O7 C8 179.25(18) . . . . ? C5 C6 N9 C10 -29.0(3) . . . . ? C1 C6 N9 C10 157.32(19) . . . . ? C6 N9 C10 C13 -14.2(3) . . . . ? C6 N9 C10 C11 167.08(18) . . . . ? N9 C10 C11 C12 179.28(19) . . . . ? C13 C10 C11 C12 0.5(3) . . . . ? N9 C10 C11 N14 -0.1(3) . . . . ? C13 C10 C11 N14 -178.89(18) . . . . ? C10 C11 C12 C11 -0.4(4) . . . 3_565 ? N14 C11 C12 C11 179.00(15) . . . 3_565 ? N9 C10 C13 C10 -179.38(15) . . . 3_565 ? C11 C10 C13 C10 -0.6(4) . . . 3_565 ? C12 C11 N14 O15 13.6(3) . . . . ? C10 C11 N14 O15 -167.02(17) . . . . ? C12 C11 N14 O16 -165.57(18) . . . . ? C10 C11 N14 O16 13.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 72.14 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.137 _refine_diff_density_min -0.122 _refine_diff_density_rms 0.031 #====END data_vm115 _database_code_depnum_ccdc_archive 'CCDC 731796' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C41 H43.80 Cl3 N8 O13.40' _chemical_formula_weight 969.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 15.4253(9) _cell_length_b 16.0157(8) _cell_length_c 18.8913(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.044(4) _cell_angle_gamma 90.00 _cell_volume 4667.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4092 _cell_measurement_theta_min 6.65 _cell_measurement_theta_max 71.63 _exptl_crystal_description platelet _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 2.391 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7960 _exptl_absorpt_correction_T_max 0.8898 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'micro-focus rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku RAXIS Rapid' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26457 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_sigmaI/netI 0.0637 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 6.65 _diffrn_reflns_theta_max 71.63 _reflns_number_total 7313 _reflns_number_gt 4092 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Some of non-coordinated solvent exhibited significant disorder and could not be modeled by discrete atoms. The contribution of the disordered solvent was subtracted from the diffraction pattern by the SQUEEZE procedure with the aid of the PLATON software (Spek, v.60709). Thus, fractional water molecules near to a centre of symmetry have been excluded and the new values of Fo have been used in the following refinements. ; _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^)+(0.0908P)^2^+11.3100P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7313 _refine_ls_number_parameters 628 _refine_ls_number_restraints 24 _refine_ls_R_factor_all 0.1356 _refine_ls_R_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.2587 _refine_ls_wR_factor_gt 0.2305 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.009 _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 0.9043(4) 0.2334(3) 0.8606(3) 0.0607(15) Uani 1 1 d . . . C2 C 0.8847(4) 0.1496(4) 0.8546(4) 0.0760(19) Uani 1 1 d . . . H2 H 0.9031 0.1193 0.8141 0.091 Uiso 1 1 calc R . . C3 C 0.8386(4) 0.1096(4) 0.9071(4) 0.0742(18) Uani 1 1 d . . . H3 H 0.8255 0.0519 0.9026 0.089 Uiso 1 1 calc R . . C4 C 0.8118(4) 0.1521(3) 0.9655(3) 0.0688(17) Uani 1 1 d . . . H4 H 0.7807 0.1238 1.0017 0.083 Uiso 1 1 calc R . . C5 C 0.8296(4) 0.2366(3) 0.9723(3) 0.0592(15) Uani 1 1 d . . . H5 H 0.8083 0.2666 1.0120 0.071 Uiso 1 1 calc R . . C6 C 0.8781(4) 0.2774(3) 0.9215(3) 0.0531(13) Uani 1 1 d . . . O7 O 0.9476(3) 0.2806(2) 0.8119(2) 0.0695(11) Uani 1 1 d . . . C8 C 0.9865(6) 0.2375(5) 0.7531(4) 0.112(3) Uani 1 1 d . . . H8A H 1.0281 0.1962 0.7708 0.168 Uiso 1 1 calc R . . H8B H 1.0166 0.2778 0.7227 0.168 Uiso 1 1 calc R . . H8C H 0.9413 0.2091 0.7257 0.168 Uiso 1 1 calc R . . N9 N 0.8989(3) 0.3631(2) 0.9213(2) 0.0521(11) Uani 1 1 d . . . H9 H 0.9170 0.3822 0.8802 0.062 Uiso 1 1 calc R . . C10 C 0.8959(3) 0.4215(3) 0.9737(3) 0.0469(12) Uani 1 1 d . . . C11 C 0.8972(3) 0.5084(3) 0.9568(2) 0.0460(12) Uani 1 1 d . . . C12 C 0.8916(3) 0.5675(3) 1.0102(3) 0.0465(12) Uani 1 1 d . . . H12 H 0.8929 0.6250 0.9979 0.056 Uiso 1 1 calc R . . C13 C 0.8842(3) 0.5461(3) 1.0801(3) 0.0463(12) Uani 1 1 d . . . C14 C 0.8834(3) 0.4595(3) 1.0995(3) 0.0450(12) Uani 1 1 d . . . C15 C 0.8917(3) 0.4008(3) 1.0449(3) 0.0482(13) Uani 1 1 d . . . H15 H 0.8947 0.3434 1.0574 0.058 Uiso 1 1 calc R . . N16 N 0.9054(3) 0.5405(3) 0.8864(2) 0.0537(11) Uani 1 1 d . . . O17 O 0.8919(3) 0.6154(2) 0.8748(2) 0.0683(11) Uani 1 1 d . . . O18 O 0.9259(3) 0.4921(2) 0.83755(19) 0.0661(11) Uani 1 1 d . . . N19 N 0.8784(3) 0.6123(2) 1.1316(3) 0.0554(12) Uani 1 1 d . . . O20 O 0.8719(3) 0.5949(2) 1.1950(2) 0.0667(11) Uani 1 1 d . . . O21 O 0.8794(3) 0.6849(2) 1.1094(2) 0.0708(12) Uani 1 1 d . . . N22 N 0.8776(3) 0.4328(2) 1.1673(2) 0.0514(11) Uani 1 1 d . . . H22 H 0.8777 0.4701 1.2015 0.062 Uiso 1 1 calc R . . C23 C 0.8714(4) 0.3461(3) 1.1855(3) 0.0507(13) Uani 1 1 d . . . C24 C 0.7966(4) 0.3014(3) 1.1681(3) 0.0507(13) Uani 1 1 d . . . C25 C 0.7933(4) 0.2165(3) 1.1841(3) 0.0533(14) Uani 1 1 d . . . H25 H 0.7434 0.1848 1.1721 0.064 Uiso 1 1 calc R . . C26 C 0.8628(4) 0.1783(3) 1.2177(3) 0.0530(14) Uani 1 1 d . . . C27 C 0.9369(4) 0.2230(3) 1.2356(3) 0.0513(13) Uani 1 1 d . . . C28 C 0.9405(4) 0.3076(3) 1.2182(3) 0.0514(13) Uani 1 1 d . . . H28 H 0.9911 0.3389 1.2291 0.062 Uiso 1 1 calc R . . O29 O 0.7333(2) 0.3463(2) 1.13584(19) 0.0575(10) Uani 1 1 d . . . C30 C 0.6585(4) 0.3029(3) 1.1101(3) 0.0542(14) Uani 1 1 d . . . H30A H 0.6254 0.2791 1.1501 0.065 Uiso 1 1 calc R . . H30B H 0.6764 0.2567 1.0785 0.065 Uiso 1 1 calc R . . C31 C 0.6024(4) 0.3649(3) 1.0695(3) 0.0562(14) Uani 1 1 d . . . H31 H 0.5887 0.4128 1.1015 0.067 Uiso 1 1 calc R . . C32 C 0.6486(4) 0.3986(4) 1.0048(3) 0.0754(18) Uani 1 1 d . . . H32A H 0.6596 0.3528 0.9716 0.113 Uiso 1 1 calc R . . H32B H 0.7038 0.4237 1.0191 0.113 Uiso 1 1 calc R . . H32C H 0.6123 0.4409 0.9819 0.113 Uiso 1 1 calc R . . C33 C 0.5186(4) 0.3228(4) 1.0493(4) 0.0807(19) Uani 1 1 d . . . H33A H 0.4807 0.3629 1.0253 0.121 Uiso 1 1 calc R . . H33B H 0.4898 0.3020 1.0920 0.121 Uiso 1 1 calc R . . H33C H 0.5308 0.2759 1.0175 0.121 Uiso 1 1 calc R . . O34 O 0.8667(3) 0.0955(2) 1.2333(2) 0.0647(11) Uani 1 1 d . . . C35 C 0.8013(4) 0.0397(3) 1.2108(3) 0.0616(16) Uani 1 1 d . . . H35A H 0.7925 0.0442 1.1590 0.074 Uiso 1 1 calc R . . H35B H 0.7458 0.0527 1.2347 0.074 Uiso 1 1 calc R . . C36 C 0.8312(5) -0.0481(3) 1.2302(3) 0.0710(18) Uani 1 1 d . . . H36 H 0.8888 -0.0581 1.2075 0.085 Uiso 1 1 calc R . . C37 C 0.8423(5) -0.0547(4) 1.3102(4) 0.097(2) Uani 1 1 d . . . H37A H 0.7863 -0.0453 1.3334 0.146 Uiso 1 1 calc R . . H37B H 0.8840 -0.0126 1.3263 0.146 Uiso 1 1 calc R . . H37C H 0.8638 -0.1105 1.3224 0.146 Uiso 1 1 calc R . . C38 C 0.7671(5) -0.1124(4) 1.2013(5) 0.100(3) Uani 1 1 d . . . H38A H 0.7100 -0.1032 1.2226 0.150 Uiso 1 1 calc R . . H38B H 0.7874 -0.1687 1.2130 0.150 Uiso 1 1 calc R . . H38C H 0.7629 -0.1065 1.1498 0.150 Uiso 1 1 calc R . . N39 N 1.0057(3) 0.1749(2) 1.2636(2) 0.0577(12) Uani 1 1 d . . . H39 H 0.9984 0.1206 1.2597 0.069 Uiso 1 1 calc R . . C40 C 1.0816(4) 0.1979(3) 1.2958(3) 0.0518(13) Uani 1 1 d . . . C41 C 1.1533(4) 0.1409(3) 1.2993(3) 0.0527(14) Uani 1 1 d . . . C42 C 1.2288(4) 0.1650(4) 1.3299(3) 0.0594(15) Uani 1 1 d . . . H42 H 1.2752 0.1260 1.3321 0.071 Uiso 1 1 calc R . . C43 C 1.2410(4) 0.2428(4) 1.3576(3) 0.0582(15) Uani 1 1 d . . . C44 C 1.1728(4) 0.3018(3) 1.3556(3) 0.0583(15) Uani 1 1 d . . . C45 C 1.0944(4) 0.2771(3) 1.3253(3) 0.0556(14) Uani 1 1 d . . . H45 H 1.0476 0.3157 1.3247 0.067 Uiso 1 1 calc R . . N46 N 1.1497(4) 0.0570(3) 1.2711(2) 0.0628(13) Uani 1 1 d . . . O47 O 1.0798(3) 0.0278(2) 1.2511(2) 0.0837(14) Uani 1 1 d . . . O48 O 1.2173(3) 0.0155(3) 1.2693(2) 0.0820(13) Uani 1 1 d . . . N49 N 1.3251(4) 0.2594(4) 1.3890(3) 0.0756(16) Uani 1 1 d . . . O50 O 1.3391(4) 0.3292(3) 1.4137(3) 0.118(2) Uani 1 1 d . . . O51 O 1.3796(3) 0.2039(3) 1.3902(2) 0.0863(14) Uani 1 1 d . . . N52 N 1.1821(4) 0.3796(3) 1.3836(2) 0.0716(15) Uani 1 1 d . . . H52 H 1.2329 0.3897 1.4030 0.086 Uiso 1 1 calc R . . C53 C 1.1228(5) 0.4464(4) 1.3861(3) 0.077(2) Uani 1 1 d . . . C54 C 1.1237(6) 0.4944(4) 1.4479(3) 0.097(3) Uani 1 1 d . . . C55 C 1.0721(8) 0.5638(5) 1.4537(4) 0.132(4) Uani 1 1 d . . . H55 H 1.0726 0.5961 1.4959 0.158 Uiso 1 1 calc R . . C56 C 1.0198(7) 0.5863(5) 1.3979(5) 0.138(4) Uani 1 1 d . . . H56 H 0.9836 0.6340 1.4023 0.166 Uiso 1 1 calc R . . C57 C 1.0185(6) 0.5410(4) 1.3357(4) 0.104(3) Uani 1 1 d . . . H57 H 0.9812 0.5565 1.2979 0.125 Uiso 1 1 calc R . . C58 C 1.0729(5) 0.4727(4) 1.3298(3) 0.083(2) Uani 1 1 d . . . H58 H 1.0758 0.4434 1.2861 0.100 Uiso 1 1 calc R . . O59 O 1.1803(4) 0.4667(3) 1.4985(2) 0.115(2) Uani 1 1 d . . . C60 C 1.1951(8) 0.5181(4) 1.5592(4) 0.136(4) Uani 1 1 d . . . H60A H 1.2145 0.5735 1.5438 0.204 Uiso 1 1 calc R . . H60B H 1.2398 0.4925 1.5890 0.204 Uiso 1 1 calc R . . H60C H 1.1412 0.5235 1.5862 0.204 Uiso 1 1 calc R . . O74 O 0.4324(8) 0.4070(8) 0.5843(5) 0.100(4) Uani 0.40 1 d P A 1 C80 C 0.2834(11) 0.2589(12) 0.6164(9) 0.110(5) Uani 0.40 1 d PDU B 2 H80 H 0.3061 0.2058 0.6374 0.132 Uiso 0.40 1 calc PR B 2 Cl81 Cl 0.2343(13) 0.3179(12) 0.6814(8) 0.184(8) Uani 0.40 1 d PDU B 2 Cl82 Cl 0.2096(6) 0.2356(5) 0.5476(4) 0.137(2) Uani 0.40 1 d PDU B 2 Cl83 Cl 0.3688(4) 0.3150(4) 0.5778(3) 0.135(2) Uani 0.40 1 d PDU B 2 C90 C 0.2245(9) 0.2885(9) 0.5809(8) 0.127(5) Uani 0.60 1 d PDU C 3 H90 H 0.2429 0.3383 0.5527 0.152 Uiso 0.60 1 calc PR C 3 Cl91 Cl 0.2052(8) 0.3167(5) 0.6675(4) 0.122(2) Uani 0.60 1 d PDU C 3 Cl92 Cl 0.1299(4) 0.2395(3) 0.5404(2) 0.1462(17) Uani 0.60 1 d PDU C 3 Cl93 Cl 0.3049(4) 0.2107(3) 0.5780(3) 0.1510(18) Uani 0.60 1 d PDU C 3 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 0.067(4) 0.035(3) 0.080(4) -0.011(3) -0.009(3) 0.005(3) C2 0.087(5) 0.044(3) 0.096(5) -0.022(3) -0.008(4) 0.001(3) C3 0.074(5) 0.038(3) 0.111(5) -0.006(3) -0.012(4) -0.010(3) C4 0.071(5) 0.044(3) 0.092(4) -0.001(3) -0.012(3) -0.015(3) C5 0.063(4) 0.042(3) 0.073(4) -0.002(2) -0.010(3) -0.007(3) C6 0.057(4) 0.034(3) 0.068(3) -0.003(2) -0.012(3) -0.004(2) O7 0.091(3) 0.047(2) 0.071(2) -0.0119(18) 0.007(2) 0.000(2) C8 0.161(8) 0.083(5) 0.092(5) -0.027(4) 0.043(5) 0.004(5) N9 0.066(3) 0.029(2) 0.061(3) -0.0054(18) 0.000(2) -0.003(2) C10 0.050(4) 0.030(3) 0.061(3) -0.002(2) -0.005(2) 0.004(2) C11 0.051(4) 0.034(3) 0.054(3) 0.005(2) -0.008(2) 0.004(2) C12 0.045(4) 0.028(2) 0.066(3) 0.003(2) -0.008(2) 0.003(2) C13 0.051(4) 0.025(2) 0.063(3) -0.004(2) -0.005(2) 0.004(2) C14 0.047(3) 0.032(3) 0.056(3) 0.001(2) -0.009(2) 0.000(2) C15 0.052(4) 0.030(3) 0.063(3) 0.000(2) -0.006(2) 0.002(2) N16 0.056(3) 0.044(3) 0.061(3) 0.007(2) -0.008(2) -0.001(2) O17 0.090(3) 0.037(2) 0.078(3) 0.0155(17) -0.005(2) 0.012(2) O18 0.091(3) 0.047(2) 0.060(2) 0.0014(18) 0.001(2) -0.002(2) N19 0.062(3) 0.032(2) 0.071(3) -0.004(2) -0.009(2) 0.002(2) O20 0.092(3) 0.047(2) 0.061(2) -0.0034(17) -0.002(2) -0.001(2) O21 0.103(3) 0.030(2) 0.079(3) -0.0029(17) -0.012(2) 0.001(2) N22 0.065(3) 0.034(2) 0.055(2) -0.0024(18) -0.009(2) -0.002(2) C23 0.072(4) 0.024(2) 0.056(3) 0.001(2) 0.000(3) -0.004(2) C24 0.058(4) 0.030(3) 0.064(3) 0.001(2) -0.003(3) -0.003(2) C25 0.060(4) 0.036(3) 0.065(3) 0.004(2) -0.005(3) -0.006(3) C26 0.064(4) 0.029(3) 0.066(3) 0.004(2) -0.005(3) -0.003(3) C27 0.059(4) 0.036(3) 0.059(3) -0.001(2) -0.003(3) 0.001(3) C28 0.060(4) 0.034(3) 0.060(3) 0.005(2) -0.009(3) -0.004(2) O29 0.059(3) 0.0328(19) 0.081(2) 0.0045(16) -0.0159(19) -0.0024(18) C30 0.055(4) 0.035(3) 0.073(3) -0.003(2) -0.003(3) -0.008(3) C31 0.054(4) 0.038(3) 0.076(4) 0.002(2) -0.011(3) -0.008(3) C32 0.077(5) 0.070(4) 0.080(4) 0.024(3) -0.004(3) 0.009(3) C33 0.073(5) 0.072(4) 0.097(5) 0.012(3) -0.021(4) -0.004(4) O34 0.072(3) 0.036(2) 0.086(3) 0.0115(17) -0.025(2) -0.0072(19) C35 0.066(4) 0.033(3) 0.086(4) 0.009(2) -0.022(3) -0.010(3) C36 0.079(5) 0.037(3) 0.097(5) 0.011(3) -0.026(4) -0.004(3) C37 0.123(7) 0.053(4) 0.115(6) 0.022(4) -0.026(5) 0.001(4) C38 0.103(6) 0.040(4) 0.158(7) 0.007(4) -0.039(5) -0.013(4) N39 0.065(4) 0.028(2) 0.080(3) -0.0039(19) -0.017(3) 0.001(2) C40 0.063(4) 0.042(3) 0.051(3) -0.003(2) -0.008(3) -0.010(3) C41 0.065(4) 0.037(3) 0.056(3) -0.005(2) -0.011(3) 0.001(3) C42 0.067(4) 0.058(4) 0.053(3) 0.005(2) -0.006(3) 0.003(3) C43 0.058(4) 0.061(4) 0.055(3) 0.008(3) -0.017(3) -0.014(3) C44 0.077(5) 0.046(3) 0.052(3) 0.003(2) -0.012(3) -0.013(3) C45 0.067(4) 0.040(3) 0.061(3) -0.002(2) -0.010(3) -0.002(3) N46 0.081(4) 0.034(3) 0.073(3) -0.001(2) -0.013(3) 0.009(3) O47 0.093(4) 0.044(2) 0.114(4) -0.017(2) -0.027(3) 0.007(2) O48 0.092(4) 0.054(3) 0.100(3) 0.001(2) -0.012(3) 0.027(3) N49 0.083(5) 0.077(4) 0.067(3) 0.017(3) -0.017(3) -0.019(4) O50 0.119(5) 0.075(4) 0.159(5) 0.015(3) -0.076(4) -0.030(3) O51 0.070(4) 0.101(4) 0.088(3) 0.011(3) -0.013(2) -0.002(3) N52 0.087(4) 0.051(3) 0.077(3) -0.003(2) -0.029(3) -0.017(3) C53 0.117(6) 0.046(4) 0.067(4) -0.003(3) -0.028(4) -0.003(4) C54 0.169(8) 0.049(4) 0.073(4) -0.003(3) -0.048(5) 0.005(4) C55 0.251(12) 0.059(5) 0.085(5) -0.013(4) -0.047(6) 0.032(6) C56 0.231(12) 0.076(5) 0.107(6) -0.020(5) -0.057(7) 0.053(7) C57 0.155(8) 0.055(4) 0.102(5) -0.001(4) -0.056(5) 0.017(5) C58 0.130(7) 0.049(4) 0.071(4) -0.001(3) -0.031(4) 0.001(4) O59 0.208(6) 0.056(3) 0.081(3) -0.011(2) -0.063(3) 0.003(3) C60 0.258(12) 0.068(5) 0.082(5) -0.018(4) -0.067(6) -0.019(6) O74 0.126(10) 0.121(9) 0.055(6) 0.032(6) -0.019(6) -0.092(8) C80 0.121(17) 0.074(14) 0.136(17) -0.011(11) 0.016(8) 0.025(10) Cl81 0.249(18) 0.141(10) 0.162(10) -0.054(8) 0.064(10) -0.006(9) Cl82 0.142(6) 0.145(7) 0.124(5) -0.006(4) -0.002(5) 0.027(5) Cl83 0.152(5) 0.130(5) 0.122(4) 0.034(4) 0.017(4) 0.010(4) C90 0.168(12) 0.088(11) 0.125(10) -0.017(9) 0.048(10) 0.025(8) Cl91 0.186(6) 0.070(3) 0.110(3) -0.006(2) 0.049(4) -0.002(3) Cl92 0.208(5) 0.110(3) 0.121(3) -0.004(2) 0.020(3) 0.016(4) Cl93 0.170(4) 0.110(3) 0.173(4) 0.008(3) 0.060(3) 0.038(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 O7 1.366(7) . ? C1 C2 1.381(8) . ? C1 C6 1.409(7) . ? C2 C3 1.379(9) . ? C3 C4 1.361(8) . ? C4 C5 1.387(7) . ? C5 C6 1.381(7) . ? C6 N9 1.410(6) . ? O7 C8 1.440(7) . ? N9 C10 1.363(6) . ? C10 C15 1.387(7) . ? C10 C11 1.427(6) . ? C11 C12 1.387(6) . ? C11 N16 1.431(6) . ? C12 C13 1.369(7) . ? C13 C14 1.436(6) . ? C13 N19 1.441(6) . ? C14 N22 1.353(6) . ? C14 C15 1.401(6) . ? N16 O17 1.236(5) . ? N16 O18 1.246(5) . ? N19 O20 1.233(5) . ? N19 O21 1.237(5) . ? N22 C23 1.435(6) . ? C23 C28 1.378(7) . ? C23 C24 1.397(7) . ? C24 O29 1.357(6) . ? C24 C25 1.393(6) . ? C25 C26 1.387(7) . ? C26 O34 1.360(6) . ? C26 C27 1.391(7) . ? C27 C28 1.394(6) . ? C27 N39 1.413(6) . ? O29 C30 1.432(6) . ? C30 C31 1.524(7) . ? C31 C33 1.507(8) . ? C31 C32 1.513(8) . ? O34 C35 1.414(6) . ? C35 C36 1.524(7) . ? C36 C38 1.528(8) . ? C36 C37 1.525(9) . ? N39 C40 1.369(7) . ? C40 C45 1.400(7) . ? C40 C41 1.436(7) . ? C41 C42 1.356(8) . ? C41 N46 1.446(6) . ? C42 C43 1.366(7) . ? C43 C44 1.415(8) . ? C43 N49 1.450(8) . ? C44 N52 1.361(7) . ? C44 C45 1.395(8) . ? N46 O47 1.235(6) . ? N46 O48 1.237(6) . ? N49 O51 1.224(7) . ? N49 O50 1.230(7) . ? N52 C53 1.409(8) . ? C53 C58 1.379(8) . ? C53 C54 1.397(8) . ? C54 O59 1.368(8) . ? C54 C55 1.371(10) . ? C55 C56 1.375(11) . ? C56 C57 1.381(10) . ? C57 C58 1.383(9) . ? O59 C60 1.430(7) . ? C80 Cl81 1.725(16) . ? C80 Cl83 1.753(15) . ? C80 Cl82 1.767(16) . ? C90 Cl91 1.723(13) . ? C90 Cl93 1.760(13) . ? C90 Cl92 1.825(15) . ? 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 O7 C1 C2 126.1(5) . . ? O7 C1 C6 114.5(5) . . ? C2 C1 C6 119.4(6) . . ? C3 C2 C1 120.3(6) . . ? C4 C3 C2 120.6(6) . . ? C3 C4 C5 120.2(6) . . ? C6 C5 C4 120.3(6) . . ? C5 C6 N9 125.8(5) . . ? C5 C6 C1 119.2(5) . . ? N9 C6 C1 114.8(5) . . ? C1 O7 C8 117.3(5) . . ? C10 N9 C6 131.2(4) . . ? N9 C10 C15 122.8(4) . . ? N9 C10 C11 120.4(4) . . ? C15 C10 C11 116.8(4) . . ? C12 C11 C10 120.1(4) . . ? C12 C11 N16 115.8(4) . . ? C10 C11 N16 124.0(4) . . ? C13 C12 C11 122.4(4) . . ? C12 C13 C14 119.3(4) . . ? C12 C13 N19 118.2(4) . . ? C14 C13 N19 122.6(4) . . ? N22 C14 C15 119.5(4) . . ? N22 C14 C13 123.1(4) . . ? C15 C14 C13 117.4(4) . . ? C10 C15 C14 123.9(4) . . ? O17 N16 O18 120.9(4) . . ? O17 N16 C11 119.9(4) . . ? O18 N16 C11 119.2(4) . . ? O20 N19 O21 122.8(4) . . ? O20 N19 C13 119.6(4) . . ? O21 N19 C13 117.5(4) . . ? C14 N22 C23 122.4(4) . . ? C28 C23 C24 121.0(4) . . ? C28 C23 N22 119.3(5) . . ? C24 C23 N22 119.7(5) . . ? O29 C24 C25 126.1(5) . . ? O29 C24 C23 115.3(4) . . ? C25 C24 C23 118.6(5) . . ? C26 C25 C24 120.1(5) . . ? O34 C26 C25 124.3(5) . . ? O34 C26 C27 114.4(5) . . ? C25 C26 C27 121.3(4) . . ? C28 C27 C26 118.4(5) . . ? C28 C27 N39 126.0(5) . . ? C26 C27 N39 115.3(4) . . ? C23 C28 C27 120.7(5) . . ? C24 O29 C30 118.3(4) . . ? O29 C30 C31 108.1(4) . . ? C33 C31 C32 111.1(5) . . ? C33 C31 C30 108.8(4) . . ? C32 C31 C30 111.7(5) . . ? C26 O34 C35 121.3(4) . . ? O34 C35 C36 107.1(5) . . ? C38 C36 C37 112.3(6) . . ? C38 C36 C35 109.9(5) . . ? C37 C36 C35 109.7(5) . . ? C40 N39 C27 131.4(4) . . ? N39 C40 C45 122.7(5) . . ? N39 C40 C41 120.6(4) . . ? C45 C40 C41 116.7(5) . . ? C42 C41 C40 120.1(5) . . ? C42 C41 N46 116.9(5) . . ? C40 C41 N46 123.0(5) . . ? C41 C42 C43 122.8(6) . . ? C42 C43 C44 119.8(5) . . ? C42 C43 N49 116.6(6) . . ? C44 C43 N49 123.6(5) . . ? N52 C44 C45 120.7(6) . . ? N52 C44 C43 121.5(6) . . ? C45 C44 C43 117.8(5) . . ? C44 C45 C40 122.9(5) . . ? O47 N46 O48 121.5(5) . . ? O47 N46 C41 119.9(5) . . ? O48 N46 C41 118.6(6) . . ? O51 N49 O50 122.2(7) . . ? O51 N49 C43 119.3(6) . . ? O50 N49 C43 118.6(7) . . ? C44 N52 C53 129.8(6) . . ? C58 C53 C54 118.8(6) . . ? C58 C53 N52 124.6(6) . . ? C54 C53 N52 116.1(6) . . ? O59 C54 C55 125.2(6) . . ? O59 C54 C53 114.2(7) . . ? C55 C54 C53 120.6(7) . . ? C54 C55 C56 119.4(7) . . ? C55 C56 C57 121.5(8) . . ? C56 C57 C58 118.5(7) . . ? C53 C58 C57 121.1(6) . . ? C54 O59 C60 118.3(6) . . ? Cl81 C80 Cl83 110.2(11) . . ? Cl81 C80 Cl82 110.8(12) . . ? Cl83 C80 Cl82 106.6(10) . . ? Cl91 C90 Cl93 109.7(10) . . ? Cl91 C90 Cl92 111.9(9) . . ? Cl93 C90 Cl92 104.2(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 O7 C1 C2 C3 -178.4(6) . . . . ? C6 C1 C2 C3 1.1(10) . . . . ? C1 C2 C3 C4 0.1(10) . . . . ? C2 C3 C4 C5 0.8(10) . . . . ? C3 C4 C5 C6 -3.0(9) . . . . ? C4 C5 C6 N9 178.4(5) . . . . ? C4 C5 C6 C1 4.1(8) . . . . ? O7 C1 C6 C5 176.3(5) . . . . ? C2 C1 C6 C5 -3.1(9) . . . . ? O7 C1 C6 N9 1.5(7) . . . . ? C2 C1 C6 N9 -178.0(5) . . . . ? C2 C1 O7 C8 -8.8(9) . . . . ? C6 C1 O7 C8 171.7(6) . . . . ? C5 C6 N9 C10 16.6(9) . . . . ? C1 C6 N9 C10 -168.9(5) . . . . ? C6 N9 C10 C15 17.5(9) . . . . ? C6 N9 C10 C11 -162.6(5) . . . . ? N9 C10 C11 C12 178.2(5) . . . . ? C15 C10 C11 C12 -2.0(7) . . . . ? N9 C10 C11 N16 -2.9(8) . . . . ? C15 C10 C11 N16 176.9(5) . . . . ? C10 C11 C12 C13 -0.4(8) . . . . ? N16 C11 C12 C13 -179.4(5) . . . . ? C11 C12 C13 C14 0.9(8) . . . . ? C11 C12 C13 N19 -179.7(5) . . . . ? C12 C13 C14 N22 179.0(5) . . . . ? N19 C13 C14 N22 -0.3(8) . . . . ? C12 C13 C14 C15 1.0(8) . . . . ? N19 C13 C14 C15 -178.4(5) . . . . ? N9 C10 C15 C14 -176.1(5) . . . . ? C11 C10 C15 C14 4.1(8) . . . . ? N22 C14 C15 C10 178.3(5) . . . . ? C13 C14 C15 C10 -3.6(8) . . . . ? C12 C11 N16 O17 -12.8(7) . . . . ? C10 C11 N16 O17 168.2(5) . . . . ? C12 C11 N16 O18 167.5(5) . . . . ? C10 C11 N16 O18 -11.5(8) . . . . ? C12 C13 N19 O20 -179.9(5) . . . . ? C14 C13 N19 O20 -0.5(8) . . . . ? C12 C13 N19 O21 0.8(7) . . . . ? C14 C13 N19 O21 -179.8(5) . . . . ? C15 C14 N22 C23 -6.0(8) . . . . ? C13 C14 N22 C23 175.9(5) . . . . ? C14 N22 C23 C28 110.0(6) . . . . ? C14 N22 C23 C24 -68.3(7) . . . . ? C28 C23 C24 O29 -179.8(5) . . . . ? N22 C23 C24 O29 -1.5(7) . . . . ? C28 C23 C24 C25 -0.4(8) . . . . ? N22 C23 C24 C25 177.8(5) . . . . ? O29 C24 C25 C26 -179.6(5) . . . . ? C23 C24 C25 C26 1.1(8) . . . . ? C24 C25 C26 O34 -177.6(5) . . . . ? C24 C25 C26 C27 -0.5(8) . . . . ? O34 C26 C27 C28 176.7(5) . . . . ? C25 C26 C27 C28 -0.7(8) . . . . ? O34 C26 C27 N39 3.0(7) . . . . ? C25 C26 C27 N39 -174.4(5) . . . . ? C24 C23 C28 C27 -0.8(8) . . . . ? N22 C23 C28 C27 -179.1(4) . . . . ? C26 C27 C28 C23 1.4(8) . . . . ? N39 C27 C28 C23 174.3(5) . . . . ? C25 C24 O29 C30 -5.6(7) . . . . ? C23 C24 O29 C30 173.7(4) . . . . ? C24 O29 C30 C31 -174.0(4) . . . . ? O29 C30 C31 C33 -173.5(5) . . . . ? O29 C30 C31 C32 63.5(6) . . . . ? C25 C26 O34 C35 5.0(8) . . . . ? C27 C26 O34 C35 -172.3(5) . . . . ? C26 O34 C35 C36 174.0(5) . . . . ? O34 C35 C36 C38 -174.8(6) . . . . ? O34 C35 C36 C37 61.3(7) . . . . ? C28 C27 N39 C40 17.6(9) . . . . ? C26 C27 N39 C40 -169.3(5) . . . . ? C27 N39 C40 C45 19.0(9) . . . . ? C27 N39 C40 C41 -159.6(5) . . . . ? N39 C40 C41 C42 178.5(5) . . . . ? C45 C40 C41 C42 -0.2(7) . . . . ? N39 C40 C41 N46 -1.3(8) . . . . ? C45 C40 C41 N46 180.0(5) . . . . ? C40 C41 C42 C43 -0.7(8) . . . . ? N46 C41 C42 C43 179.1(5) . . . . ? C41 C42 C43 C44 0.6(8) . . . . ? C41 C42 C43 N49 179.6(5) . . . . ? C42 C43 C44 N52 179.0(5) . . . . ? N49 C43 C44 N52 0.1(8) . . . . ? C42 C43 C44 C45 0.6(8) . . . . ? N49 C43 C44 C45 -178.4(5) . . . . ? N52 C44 C45 C40 179.9(5) . . . . ? C43 C44 C45 C40 -1.6(8) . . . . ? N39 C40 C45 C44 -177.3(5) . . . . ? C41 C40 C45 C44 1.4(8) . . . . ? C42 C41 N46 O47 170.6(5) . . . . ? C40 C41 N46 O47 -9.6(8) . . . . ? C42 C41 N46 O48 -7.8(7) . . . . ? C40 C41 N46 O48 172.0(5) . . . . ? C42 C43 N49 O51 -1.1(8) . . . . ? C44 C43 N49 O51 177.9(5) . . . . ? C42 C43 N49 O50 179.1(6) . . . . ? C44 C43 N49 O50 -1.9(8) . . . . ? C45 C44 N52 C53 -2.2(9) . . . . ? C43 C44 N52 C53 179.4(6) . . . . ? C44 N52 C53 C58 -45.6(10) . . . . ? C44 N52 C53 C54 142.5(7) . . . . ? C58 C53 C54 O59 -175.1(7) . . . . ? N52 C53 C54 O59 -2.7(10) . . . . ? C58 C53 C54 C55 3.6(13) . . . . ? N52 C53 C54 C55 176.0(8) . . . . ? O59 C54 C55 C56 178.1(9) . . . . ? C53 C54 C55 C56 -0.5(15) . . . . ? C54 C55 C56 C57 -0.7(17) . . . . ? C55 C56 C57 C58 -1.3(16) . . . . ? C54 C53 C58 C57 -5.7(12) . . . . ? N52 C53 C58 C57 -177.4(7) . . . . ? C56 C57 C58 C53 4.5(13) . . . . ? C55 C54 O59 C60 -7.5(13) . . . . ? C53 C54 O59 C60 171.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.801 _diffrn_reflns_theta_full 71.63 _diffrn_measured_fraction_theta_full 0.801 _refine_diff_density_max 0.626 _refine_diff_density_min -0.390 _refine_diff_density_rms 0.075 _vrf_REFLT03 ; PROBLEM: Reflection count<85% complete RESPONSE: instability of the crystal did not permit a complete data ; _vrf_PLAT432 ; PROBLEM: Short Inter X...Y Contact Cl93 .. C55 .. 3.09 Ang. RESPONSE: a bad statistical position of disordered solvent explain this short distance ; _vrf_CHEMW03 ; PROBLEM: The ratio given/expected molecular weight as calculated from the _atom_site data lies outside the range 0.99<>1.01 RESPONSE: The quoted formula includes disordered solvent modelled by PLATON/SQUEEZE and not part of the atom list ; #====END data_vm35jap _database_code_depnum_ccdc_archive 'CCDC 731797' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H66 N12 O18' _chemical_formula_weight 1243.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 18.0066(9) _cell_length_b 33.8684(11) _cell_length_c 20.2630(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.719(2) _cell_angle_gamma 90.00 _cell_volume 12343.6(10) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4476 _cell_measurement_theta_min 6.74 _cell_measurement_theta_max 72.45 _exptl_crystal_description prism _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5232 _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8497 _exptl_absorpt_correction_T_max 0.9206 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'micro-focus rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku RAXIS Rapid' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 85375 _diffrn_reflns_av_R_equivalents 0.0751 _diffrn_reflns_av_sigmaI/netI 0.0758 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -41 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 6.74 _diffrn_reflns_theta_max 72.45 _reflns_number_total 11511 _reflns_number_gt 4476 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Isobutyl lateral chains are frequently disordered without reveal two discrete positions as for C35 and C60 groups. We can not discriminate disorder on the other lateral chains and so thermal parameters are higher. The higher electronic residue is equal to 0.216. ; _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^)+(0.1202P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11511 _refine_ls_number_parameters 774 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1780 _refine_ls_R_factor_gt 0.0778 _refine_ls_wR_factor_ref 0.2655 _refine_ls_wR_factor_gt 0.2243 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.007 _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 0.8638(3) 0.2520(2) 0.4733(2) 0.229(4) Uani 1 1 d . . . H1A H 0.9024 0.2316 0.4733 0.343 Uiso 1 1 calc R . . H1B H 0.8440 0.2538 0.5174 0.343 Uiso 1 1 calc R . . H1C H 0.8852 0.2774 0.4613 0.343 Uiso 1 1 calc R . . O2 O 0.80439(19) 0.24173(14) 0.42576(17) 0.1831(18) Uani 1 1 d . . . C3 C 0.7707(2) 0.20584(14) 0.43184(18) 0.162(2) Uani 1 1 d G . . C4 C 0.7906(2) 0.17651(17) 0.47728(15) 0.208(4) Uani 1 1 d G . . H4 H 0.8334 0.1798 0.5060 0.250 Uiso 1 1 calc R . . C5 C 0.7480(3) 0.14244(14) 0.48067(16) 0.222(4) Uani 1 1 d G . . H5 H 0.7616 0.1224 0.5117 0.266 Uiso 1 1 calc R . . C6 C 0.6854(3) 0.13768(11) 0.4386(2) 0.191(3) Uani 1 1 d G . . H6 H 0.6562 0.1144 0.4409 0.229 Uiso 1 1 calc R . . C7 C 0.66543(19) 0.16701(13) 0.39317(15) 0.1441(19) Uani 1 1 d G . . H7 H 0.6226 0.1638 0.3644 0.173 Uiso 1 1 calc R . . C8 C 0.7081(2) 0.20109(11) 0.38978(13) 0.1284(17) Uani 1 1 d G . . N9 N 0.68874(19) 0.23339(11) 0.34856(16) 0.1238(12) Uani 1 1 d . . . H9 H 0.7078 0.2561 0.3617 0.149 Uiso 1 1 calc R . . C10 C 0.64442(15) 0.23522(9) 0.29054(11) 0.1110(13) Uani 1 1 d G . . C11 C 0.62734(14) 0.20095(8) 0.25526(13) 0.1040(13) Uani 1 1 d G . . H11 H 0.6458 0.1762 0.2708 0.125 Uiso 1 1 calc R . . C12 C 0.58321(15) 0.20287(8) 0.19718(12) 0.0986(12) Uani 1 1 d G . . C13 C 0.55618(14) 0.23907(9) 0.17437(10) 0.1058(13) Uani 1 1 d G . . C14 C 0.57327(15) 0.27334(8) 0.20964(14) 0.1136(14) Uani 1 1 d G . . H14 H 0.5548 0.2981 0.1941 0.136 Uiso 1 1 calc R . . C15 C 0.61739(17) 0.27142(8) 0.26773(14) 0.1163(14) Uani 1 1 d G . . N16 N 0.5096(2) 0.24510(14) 0.11439(18) 0.1163(12) Uani 1 1 d . . . O17 O 0.49658(16) 0.21587(10) 0.07711(14) 0.1257(10) Uani 1 1 d . . . O18 O 0.48347(18) 0.27765(10) 0.10291(14) 0.1399(12) Uani 1 1 d . . . N19 N 0.6318(3) 0.30891(13) 0.2999(2) 0.1408(14) Uani 1 1 d . . . O20 O 0.6800(2) 0.31123(10) 0.34549(18) 0.1719(15) Uani 1 1 d . . . O21 O 0.5955(2) 0.33776(11) 0.28184(17) 0.1647(14) Uani 1 1 d . . . N22 N 0.56584(16) 0.16915(10) 0.16187(14) 0.1040(10) Uani 1 1 d . . . H22 H 0.5416 0.1733 0.1238 0.125 Uiso 1 1 calc R . . C23 C 0.58025(15) 0.12868(8) 0.17638(15) 0.0971(12) Uani 1 1 d G . . C24 C 0.58439(15) 0.10394(11) 0.12194(10) 0.1052(13) Uani 1 1 d G . . C25 C 0.59304(15) 0.06349(10) 0.13093(13) 0.1108(13) Uani 1 1 d G . . H25 H 0.5959 0.0466 0.0937 0.133 Uiso 1 1 calc R . . C26 C 0.59757(15) 0.04777(8) 0.19436(16) 0.1063(13) Uani 1 1 d G . . C27 C 0.59344(14) 0.07251(10) 0.24880(11) 0.0952(11) Uani 1 1 d G . . C28 C 0.58478(14) 0.11296(9) 0.23981(11) 0.0939(11) Uani 1 1 d G . . H28 H 0.5820 0.1299 0.2770 0.113 Uiso 1 1 calc R . . O29 O 0.57691(16) 0.12103(8) 0.06229(12) 0.1222(10) Uani 1 1 d . . . C30 C 0.5830(3) 0.09744(15) 0.0040(2) 0.1421(17) Uani 1 1 d . . . H30A H 0.5455 0.0761 0.0029 0.170 Uiso 1 1 calc R . . H30B H 0.6330 0.0854 0.0032 0.170 Uiso 1 1 calc R . . C31 C 0.5697(5) 0.12488(19) -0.0549(2) 0.182(3) Uani 1 1 d . . . H31 H 0.6068 0.1469 -0.0527 0.219 Uiso 1 1 calc R . . C32 C 0.5827(5) 0.0978(2) -0.1172(2) 0.266(4) Uani 1 1 d . . . H32A H 0.6347 0.0893 -0.1164 0.399 Uiso 1 1 calc R . . H32B H 0.5710 0.1128 -0.1577 0.399 Uiso 1 1 calc R . . H32C H 0.5503 0.0746 -0.1159 0.399 Uiso 1 1 calc R . . C33 C 0.4900(4) 0.1418(2) -0.0546(3) 0.226(3) Uani 1 1 d . . . H33A H 0.4543 0.1201 -0.0522 0.338 Uiso 1 1 calc R . . H33B H 0.4794 0.1569 -0.0952 0.338 Uiso 1 1 calc R . . H33C H 0.4857 0.1592 -0.0163 0.338 Uiso 1 1 calc R . . O34 O 0.60907(16) 0.00812(10) 0.20813(15) 0.1258(10) Uani 1 1 d . . . C35 C 0.6319(3) -0.01614(16) 0.1543(2) 0.1420(17) Uani 1 1 d D B . H35A H 0.6766 -0.0048 0.1348 0.170 Uiso 1 1 calc R . . H35B H 0.5917 -0.0177 0.1193 0.170 Uiso 1 1 calc R . . C36 C 0.6493(4) -0.0572(2) 0.1823(3) 0.175(2) Uani 1 1 d D . . H36 H 0.6924 -0.0533 0.2146 0.210 Uiso 1 1 calc R A 1 C37 C 0.6803(4) -0.08224(16) 0.1262(3) 0.215(3) Uani 1 1 d D B . H37A H 0.6401 -0.0883 0.0935 0.323 Uiso 1 1 calc R . . H37B H 0.7011 -0.1069 0.1445 0.323 Uiso 1 1 calc R . . H37C H 0.7193 -0.0674 0.1050 0.323 Uiso 1 1 calc R . . C38 C 0.5921(7) -0.0743(3) 0.2203(5) 0.174(5) Uani 0.50 1 d PD B 1 H38A H 0.5729 -0.0544 0.2500 0.261 Uiso 0.50 1 calc PR B 1 H38B H 0.6127 -0.0965 0.2463 0.261 Uiso 0.50 1 calc PR B 1 H38C H 0.5515 -0.0838 0.1904 0.261 Uiso 0.50 1 calc PR B 1 C38' C 0.7064(9) -0.0538(3) 0.2381(7) 0.227(6) Uani 0.50 1 d PD B 2 H38D H 0.6872 -0.0369 0.2727 0.340 Uiso 0.50 1 calc PR B 2 H38E H 0.7519 -0.0421 0.2218 0.340 Uiso 0.50 1 calc PR B 2 H38F H 0.7175 -0.0800 0.2563 0.340 Uiso 0.50 1 calc PR B 2 N39 N 0.60514(19) 0.05654(9) 0.31380(14) 0.1057(10) Uani 1 1 d . . . H39 H 0.5672 0.0536 0.3392 0.127 Uiso 1 1 calc R . . C40 C 0.67613(14) 0.04573(7) 0.33702(14) 0.0959(11) Uani 1 1 d G . . C41 C 0.69103(17) 0.02926(7) 0.39907(12) 0.0934(12) Uani 1 1 d G . . C42 C 0.76365(19) 0.01978(7) 0.41945(10) 0.1014(12) Uani 1 1 d G . . H42 H 0.7738 0.0085 0.4619 0.122 Uiso 1 1 calc R . . C43 C 0.82136(15) 0.02679(7) 0.37780(13) 0.0917(12) Uani 1 1 d G . . C44 C 0.80646(15) 0.04327(7) 0.31575(12) 0.0908(11) Uani 1 1 d G . . C45 C 0.73384(17) 0.05274(7) 0.29536(10) 0.0920(11) Uani 1 1 d G . . H45 H 0.7237 0.0640 0.2530 0.110 Uiso 1 1 calc R . . N46 N 0.6361(3) 0.01890(11) 0.4448(2) 0.1164(12) Uani 1 1 d . . . O47 O 0.5702(2) 0.02849(11) 0.43087(16) 0.1579(13) Uani 1 1 d . . . O48 O 0.65223(19) 0.00103(10) 0.49542(16) 0.1495(12) Uani 1 1 d . . . N49 N 0.8930(3) 0.01640(11) 0.4039(2) 0.1136(12) Uani 1 1 d . . . O50 O 0.9467(2) 0.02308(11) 0.36983(17) 0.1537(14) Uani 1 1 d . . . O51 O 0.90350(16) 0.00161(9) 0.45780(14) 0.1343(11) Uani 1 1 d . . . N52 N 0.86032(18) 0.04969(9) 0.27177(13) 0.1042(10) Uani 1 1 d . . . H52 H 0.9066 0.0443 0.2846 0.125 Uiso 1 1 calc R . . C53 C 0.84676(14) 0.06462(9) 0.20628(10) 0.0917(11) Uani 1 1 d G . . C54 C 0.86104(14) 0.04103(7) 0.15220(14) 0.0943(11) Uani 1 1 d G . . C55 C 0.84810(14) 0.05551(8) 0.08851(11) 0.0933(11) Uani 1 1 d G . . H55 H 0.8579 0.0394 0.0515 0.112 Uiso 1 1 calc R . . C56 C 0.82088(14) 0.09359(8) 0.07890(9) 0.0927(11) Uani 1 1 d G . . C57 C 0.80660(14) 0.11718(7) 0.13298(13) 0.0884(11) Uani 1 1 d G . . C58 C 0.81954(14) 0.10270(8) 0.19667(10) 0.0955(11) Uani 1 1 d G . . H58 H 0.8098 0.1188 0.2336 0.115 Uiso 1 1 calc R . . O59 O 0.88625(15) 0.00385(8) 0.16617(12) 0.1102(9) Uani 1 1 d . D . C60 C 0.8959(2) -0.02258(13) 0.11159(19) 0.1070(13) Uani 1 1 d D . . H60A H 0.9332 -0.0118 0.0821 0.128 Uiso 1 1 calc R C 3 H60B H 0.8483 -0.0258 0.0857 0.128 Uiso 1 1 calc R C 3 C61 C 0.9218(11) -0.0620(5) 0.1390(8) 0.115(13) Uani 0.50 1 d PD D 3 H61 H 0.9732 -0.0602 0.1597 0.138 Uiso 0.50 1 calc PR D 3 C62 C 0.8670(9) -0.0717(4) 0.1885(7) 0.220(8) Uani 0.50 1 d PD D 3 H62A H 0.8174 -0.0735 0.1667 0.330 Uiso 0.50 1 calc PR D 3 H62B H 0.8674 -0.0510 0.2223 0.330 Uiso 0.50 1 calc PR D 3 H62C H 0.8801 -0.0971 0.2092 0.330 Uiso 0.50 1 calc PR D 3 C63 C 0.9178(18) -0.0922(6) 0.0834(11) 0.181(12) Uani 0.50 1 d PD D 3 H63A H 0.9265 -0.1186 0.1017 0.271 Uiso 0.50 1 calc PR D 3 H63B H 0.9558 -0.0862 0.0519 0.271 Uiso 0.50 1 calc PR D 3 H63C H 0.8685 -0.0912 0.0608 0.271 Uiso 0.50 1 calc PR D 3 C61' C 0.9152(12) -0.0639(6) 0.1364(10) 0.134(16) Uani 0.50 1 d PD D 4 H61' H 0.8730 -0.0755 0.1602 0.161 Uiso 0.50 1 calc PR D 4 C62' C 0.9886(6) -0.0644(2) 0.1816(5) 0.147(4) Uani 0.50 1 d PD D 4 H62D H 1.0031 -0.0918 0.1909 0.221 Uiso 0.50 1 calc PR D 4 H62E H 0.9801 -0.0507 0.2232 0.221 Uiso 0.50 1 calc PR D 4 H62F H 1.0284 -0.0511 0.1589 0.221 Uiso 0.50 1 calc PR D 4 C63' C 0.9330(14) -0.0891(5) 0.0771(9) 0.136(8) Uani 0.50 1 d PD D 4 H63E H 0.8884 -0.0918 0.0479 0.204 Uiso 0.50 1 calc PR D 4 H63F H 0.9496 -0.1153 0.0923 0.204 Uiso 0.50 1 calc PR D 4 H63G H 0.9725 -0.0765 0.0530 0.204 Uiso 0.50 1 calc PR D 4 O64 O 0.80672(14) 0.11061(7) 0.01872(11) 0.1058(8) Uani 1 1 d . . . C65 C 0.8176(3) 0.08734(12) -0.03877(18) 0.1276(16) Uani 1 1 d . . . H65A H 0.7819 0.0651 -0.0411 0.153 Uiso 1 1 calc R . . H65B H 0.8687 0.0764 -0.0374 0.153 Uiso 1 1 calc R . . C66 C 0.8054(4) 0.11392(16) -0.09807(19) 0.153(2) Uani 1 1 d . . . H66 H 0.7540 0.1251 -0.0977 0.184 Uiso 1 1 calc R . . C67 C 0.8604(3) 0.14757(18) -0.0978(3) 0.169(2) Uani 1 1 d . . . H67A H 0.9111 0.1370 -0.0939 0.254 Uiso 1 1 calc R . . H67B H 0.8520 0.1650 -0.0603 0.254 Uiso 1 1 calc R . . H67C H 0.8537 0.1625 -0.1391 0.254 Uiso 1 1 calc R . . C68 C 0.8103(7) 0.0867(2) -0.1592(2) 0.336(7) Uani 1 1 d . . . H68A H 0.7969 0.1018 -0.1994 0.504 Uiso 1 1 calc R . . H68B H 0.7760 0.0645 -0.1554 0.504 Uiso 1 1 calc R . . H68C H 0.8612 0.0768 -0.1616 0.504 Uiso 1 1 calc R . . N69 N 0.77697(16) 0.15545(10) 0.11905(13) 0.0972(9) Uani 1 1 d . . . H69 H 0.7457 0.1567 0.0844 0.117 Uiso 1 1 calc R . . C70 C 0.78972(15) 0.19058(7) 0.15132(11) 0.0925(11) Uani 1 1 d G . . C71 C 0.75392(14) 0.22480(9) 0.12921(11) 0.1045(13) Uani 1 1 d G . . C72 C 0.76734(17) 0.26032(8) 0.16200(14) 0.1232(15) Uani 1 1 d G . . H72 H 0.7429 0.2837 0.1469 0.148 Uiso 1 1 calc R . . C73 C 0.81657(18) 0.26162(7) 0.21691(14) 0.1226(16) Uani 1 1 d G . . C74 C 0.85237(15) 0.22740(8) 0.23903(11) 0.1147(15) Uani 1 1 d G . . C75 C 0.83895(15) 0.19188(7) 0.20623(12) 0.1014(13) Uani 1 1 d G . . H75 H 0.8634 0.1685 0.2213 0.122 Uiso 1 1 calc R . . N76 N 0.7033(2) 0.22737(14) 0.07143(17) 0.1163(12) Uani 1 1 d . . . O77 O 0.69555(17) 0.19825(11) 0.03562(15) 0.1346(11) Uani 1 1 d . . . O78 O 0.67225(19) 0.25822(11) 0.05815(14) 0.1568(14) Uani 1 1 d . . . N79 N 0.8270(3) 0.30037(13) 0.2462(2) 0.1578(17) Uani 1 1 d . . . O80 O 0.7867(3) 0.32750(11) 0.22687(17) 0.1923(18) Uani 1 1 d . . . O81 O 0.8762(3) 0.30557(10) 0.28993(18) 0.1920(18) Uani 1 1 d . . . N82 N 0.9016(2) 0.22885(11) 0.29435(16) 0.1407(15) Uani 1 1 d . . . H82 H 0.9164 0.2527 0.3063 0.169 Uiso 1 1 calc R . . C83 C 0.9315(2) 0.19759(11) 0.33419(13) 0.139(2) Uani 1 1 d G . . C84 C 0.90073(19) 0.16006(13) 0.33797(15) 0.173(3) Uani 1 1 d G . . H84 H 0.8575 0.1535 0.3115 0.208 Uiso 1 1 calc R . . C85 C 0.9332(3) 0.13211(10) 0.38047(18) 0.177(3) Uani 1 1 d G . . H85 H 0.9122 0.1065 0.3831 0.213 Uiso 1 1 calc R . . C86 C 0.9964(2) 0.14169(13) 0.41920(15) 0.179(3) Uani 1 1 d G . . H86 H 1.0186 0.1226 0.4483 0.214 Uiso 1 1 calc R . . C87 C 1.02715(16) 0.17922(16) 0.41543(14) 0.164(3) Uani 1 1 d G . . H87 H 1.0704 0.1858 0.4419 0.197 Uiso 1 1 calc R . . C88 C 0.9947(2) 0.20717(12) 0.37292(17) 0.1366(18) Uani 1 1 d G . . O89 O 1.0182(2) 0.24518(12) 0.36867(14) 0.1539(13) Uani 1 1 d . . . C90 C 1.0672(3) 0.26027(18) 0.4201(2) 0.194(3) Uani 1 1 d . . . H90A H 1.0525 0.2500 0.4628 0.291 Uiso 1 1 calc R . . H90B H 1.0646 0.2892 0.4204 0.291 Uiso 1 1 calc R . . H90C H 1.1182 0.2520 0.4125 0.291 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 0.104(4) 0.430(11) 0.146(5) -0.129(6) -0.059(4) 0.032(5) O2 0.116(3) 0.305(5) 0.122(3) -0.081(3) -0.057(2) 0.030(3) C3 0.138(5) 0.245(7) 0.098(4) -0.058(4) -0.048(4) 0.068(5) C4 0.220(7) 0.307(9) 0.091(4) -0.010(5) -0.063(4) 0.134(7) C5 0.301(11) 0.251(8) 0.111(5) 0.030(5) -0.014(6) 0.155(8) C6 0.308(9) 0.180(5) 0.082(3) 0.013(3) -0.025(4) 0.101(5) C7 0.191(5) 0.147(4) 0.090(3) -0.011(3) -0.036(3) 0.053(4) C8 0.139(4) 0.164(5) 0.077(3) -0.024(3) -0.050(3) 0.053(3) N9 0.119(3) 0.149(3) 0.099(3) -0.012(2) -0.040(2) 0.002(2) C10 0.106(3) 0.134(4) 0.089(3) 0.008(3) -0.036(2) 0.001(3) C11 0.098(3) 0.129(3) 0.082(3) -0.005(2) -0.032(2) 0.012(2) C12 0.098(3) 0.123(3) 0.072(3) -0.002(2) -0.026(2) 0.008(2) C13 0.104(3) 0.134(3) 0.075(3) 0.010(2) -0.037(2) -0.008(3) C14 0.106(3) 0.132(4) 0.099(3) 0.017(2) -0.033(3) -0.002(3) C15 0.123(4) 0.122(4) 0.100(3) 0.003(3) -0.036(3) -0.009(3) N16 0.108(3) 0.144(3) 0.093(3) 0.018(2) -0.035(2) 0.007(3) O17 0.123(2) 0.160(3) 0.0886(19) 0.0079(18) -0.0456(17) -0.0015(19) O18 0.147(3) 0.145(3) 0.122(2) 0.0185(19) -0.058(2) 0.018(2) N19 0.163(4) 0.125(4) 0.130(4) 0.001(3) -0.045(3) -0.006(3) O20 0.186(3) 0.168(3) 0.152(3) -0.003(2) -0.086(3) -0.030(2) O21 0.205(4) 0.128(3) 0.155(3) -0.013(2) -0.061(3) 0.001(2) N22 0.094(2) 0.142(3) 0.073(2) 0.0038(19) -0.0270(17) 0.013(2) C23 0.082(3) 0.135(4) 0.072(3) -0.003(3) -0.022(2) 0.003(2) C24 0.104(3) 0.146(4) 0.063(3) -0.005(3) -0.018(2) 0.004(3) C25 0.104(3) 0.152(4) 0.076(3) -0.012(3) -0.009(2) -0.003(3) C26 0.096(3) 0.135(4) 0.086(3) -0.002(3) -0.010(2) 0.005(3) C27 0.079(3) 0.147(4) 0.059(2) -0.008(3) 0.001(2) 0.005(2) C28 0.079(3) 0.133(3) 0.069(3) -0.007(2) -0.0096(19) 0.016(2) O29 0.140(2) 0.164(2) 0.0610(16) -0.0056(16) -0.0189(16) -0.0060(18) C30 0.169(5) 0.187(5) 0.069(3) -0.022(3) -0.006(3) -0.029(3) C31 0.253(8) 0.227(6) 0.064(3) 0.006(4) -0.033(4) -0.058(6) C32 0.377(11) 0.362(9) 0.059(3) -0.044(5) 0.007(4) -0.108(8) C33 0.215(8) 0.307(9) 0.144(5) 0.025(5) -0.092(5) -0.033(6) O34 0.148(3) 0.129(2) 0.101(2) -0.0035(19) 0.0040(18) -0.0003(19) C35 0.174(5) 0.138(4) 0.113(4) -0.032(4) -0.003(3) -0.007(4) C36 0.229(8) 0.148(6) 0.143(5) -0.036(5) -0.042(5) -0.006(5) C37 0.289(8) 0.159(5) 0.196(6) -0.082(5) 0.008(6) -0.018(5) C38 0.242(14) 0.146(9) 0.138(9) 0.016(6) 0.046(9) -0.076(9) C38' 0.30(2) 0.157(10) 0.225(15) -0.019(10) -0.012(14) 0.036(11) N39 0.096(2) 0.141(3) 0.080(2) 0.0104(19) 0.0022(19) 0.0081(19) C40 0.106(3) 0.110(3) 0.071(3) 0.001(2) -0.002(3) 0.008(2) C41 0.112(4) 0.113(3) 0.056(2) 0.010(2) 0.011(3) 0.008(2) C42 0.135(4) 0.092(3) 0.076(3) 0.003(2) -0.009(3) 0.017(3) C43 0.097(3) 0.119(3) 0.059(2) 0.010(2) -0.007(2) 0.030(2) C44 0.108(3) 0.109(3) 0.056(2) 0.001(2) 0.005(2) 0.024(2) C45 0.088(3) 0.127(3) 0.061(2) 0.005(2) -0.002(2) 0.011(2) N46 0.120(4) 0.139(3) 0.090(3) 0.016(2) 0.004(3) 0.004(3) O47 0.123(3) 0.236(4) 0.116(3) 0.047(2) 0.025(2) 0.007(3) O48 0.157(3) 0.193(3) 0.099(2) 0.058(2) 0.006(2) -0.007(2) N49 0.123(3) 0.143(3) 0.074(3) 0.020(2) 0.004(3) 0.024(3) O50 0.115(3) 0.236(4) 0.109(3) 0.051(2) -0.005(2) 0.061(3) O51 0.135(2) 0.178(3) 0.087(2) 0.0453(19) -0.0166(18) 0.0164(19) N52 0.105(3) 0.148(3) 0.0583(19) 0.0042(18) -0.0087(18) 0.032(2) C53 0.084(3) 0.132(3) 0.059(2) -0.003(2) -0.001(2) 0.015(2) C54 0.084(3) 0.126(3) 0.072(3) -0.001(2) -0.007(2) 0.008(2) C55 0.099(3) 0.117(3) 0.064(2) -0.003(2) 0.002(2) 0.007(2) C56 0.101(3) 0.122(3) 0.054(2) -0.005(2) -0.008(2) 0.001(2) C57 0.084(3) 0.118(3) 0.062(2) -0.007(2) -0.0079(19) 0.019(2) C58 0.099(3) 0.128(3) 0.059(2) -0.005(2) -0.004(2) 0.014(2) O59 0.124(2) 0.126(2) 0.0799(18) 0.0012(16) -0.0014(15) 0.0247(17) C60 0.110(3) 0.131(4) 0.080(3) -0.019(3) -0.006(2) -0.008(3) C61 0.13(2) 0.13(2) 0.080(15) -0.027(14) 0.001(13) 0.016(16) C62 0.255(19) 0.155(10) 0.253(17) 0.081(10) 0.034(14) -0.026(10) C63 0.23(3) 0.153(19) 0.16(2) -0.028(16) 0.034(14) -0.037(14) C61' 0.10(2) 0.12(2) 0.17(3) 0.015(18) -0.054(18) 0.012(15) C62' 0.171(10) 0.107(6) 0.155(8) -0.011(5) -0.089(8) 0.037(6) C63' 0.138(12) 0.125(14) 0.139(15) -0.058(12) -0.056(11) 0.049(10) O64 0.137(2) 0.1284(19) 0.0509(15) -0.0060(14) -0.0097(14) 0.0093(16) C65 0.187(5) 0.139(3) 0.055(2) -0.009(2) -0.009(3) 0.021(3) C66 0.259(7) 0.149(4) 0.051(3) -0.009(3) -0.006(3) 0.050(4) C67 0.184(6) 0.178(5) 0.148(5) 0.062(4) 0.034(4) 0.055(4) C68 0.73(2) 0.214(6) 0.060(3) -0.007(4) 0.020(6) 0.158(9) N69 0.092(2) 0.135(3) 0.0628(19) -0.0026(17) -0.0179(16) 0.0137(19) C70 0.096(3) 0.122(3) 0.058(2) -0.012(2) -0.008(2) 0.027(2) C71 0.121(3) 0.130(3) 0.061(2) -0.002(2) -0.017(2) 0.042(3) C72 0.147(4) 0.142(4) 0.078(3) -0.001(3) -0.019(3) 0.065(3) C73 0.181(5) 0.112(3) 0.072(3) -0.016(2) -0.024(3) 0.054(3) C74 0.144(4) 0.127(4) 0.069(3) -0.008(2) -0.030(3) 0.044(3) C75 0.126(3) 0.109(3) 0.065(2) -0.014(2) -0.028(2) 0.032(2) N76 0.119(3) 0.159(4) 0.069(2) 0.009(2) -0.018(2) 0.042(3) O77 0.138(3) 0.174(3) 0.088(2) -0.0008(19) -0.0410(18) 0.027(2) O78 0.167(3) 0.192(3) 0.107(2) 0.007(2) -0.045(2) 0.078(3) N79 0.231(5) 0.124(3) 0.113(3) -0.009(3) -0.047(3) 0.055(3) O80 0.281(5) 0.136(3) 0.153(3) -0.016(2) -0.066(3) 0.080(3) O81 0.274(5) 0.151(3) 0.141(3) -0.039(2) -0.097(3) 0.054(3) N82 0.189(4) 0.137(3) 0.091(2) -0.025(2) -0.055(3) 0.043(2) C83 0.171(5) 0.162(5) 0.079(3) -0.029(3) -0.056(3) 0.069(4) C84 0.278(7) 0.145(4) 0.089(3) -0.019(3) -0.065(4) 0.048(5) C85 0.263(7) 0.168(5) 0.096(4) 0.007(3) -0.051(4) 0.071(4) C86 0.206(7) 0.239(7) 0.091(4) 0.038(4) 0.009(4) 0.105(5) C87 0.152(5) 0.274(7) 0.066(3) 0.019(4) -0.008(3) 0.085(5) C88 0.141(4) 0.177(5) 0.089(3) -0.023(4) -0.021(3) 0.047(4) O89 0.161(3) 0.212(3) 0.085(2) -0.041(2) -0.039(2) 0.027(3) C90 0.166(5) 0.298(7) 0.112(4) -0.090(4) -0.052(4) 0.042(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.447(5) . ? O2 C3 1.367(5) . ? C3 C4 1.3900 . ? C3 C8 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C6 C7 1.3900 . ? C7 C8 1.3900 . ? C8 N9 1.410(4) . ? N9 C10 1.391(3) . ? C10 C11 1.3900 . ? C10 C15 1.3900 . ? C11 C12 1.3900 . ? C12 N22 1.376(4) . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C13 N16 1.458(3) . ? C14 C15 1.3900 . ? C15 N19 1.445(4) . ? N16 O18 1.217(4) . ? N16 O17 1.261(4) . ? N19 O21 1.221(4) . ? N19 O20 1.240(4) . ? N22 C23 1.423(4) . ? C23 C24 1.3900 . ? C23 C28 1.3900 . ? C24 O29 1.341(3) . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? C26 O34 1.385(4) . ? C26 C27 1.3900 . ? C27 C28 1.3900 . ? C27 N39 1.430(3) . ? O29 C30 1.435(4) . ? C30 C31 1.522(6) . ? C31 C33 1.547(9) . ? C31 C32 1.586(7) . ? O34 C35 1.442(5) . ? C35 C36 1.530(6) . ? C36 C38 1.437(9) . ? C36 C38' 1.496(13) . ? C36 C37 1.543(7) . ? N39 C40 1.390(4) . ? C40 C41 1.3900 . ? C40 C45 1.3900 . ? C41 C42 1.3900 . ? C41 N46 1.430(4) . ? C42 C43 1.3900 . ? C43 C44 1.3900 . ? C43 N49 1.415(4) . ? C44 N52 1.365(3) . ? C44 C45 1.3900 . ? N46 O48 1.214(4) . ? N46 O47 1.250(4) . ? N49 O51 1.207(4) . ? N49 O50 1.236(4) . ? N52 C53 1.430(3) . ? C53 C54 1.3900 . ? C53 C58 1.3900 . ? C54 O59 1.364(3) . ? C54 C55 1.3900 . ? C55 C56 1.3900 . ? C56 O64 1.362(3) . ? C56 C57 1.3900 . ? C57 C58 1.3900 . ? C57 N69 1.425(3) . ? O59 C60 1.440(4) . ? C60 C61' 1.52(2) . ? C60 C61 1.510(17) . ? C61 C62 1.476(16) . ? C61 C63 1.520(14) . ? C61' C63' 1.521(16) . ? C61' C62' 1.571(16) . ? O64 C65 1.428(4) . ? C65 C66 1.509(5) . ? C66 C67 1.509(7) . ? C66 C68 1.550(6) . ? N69 C70 1.372(3) . ? C70 C71 1.3900 . ? C70 C75 1.3900 . ? C71 C72 1.3900 . ? C71 N76 1.452(4) . ? C72 C73 1.3900 . ? C73 C74 1.3900 . ? C73 N79 1.449(5) . ? C74 C75 1.3900 . ? C74 N82 1.397(3) . ? N76 O78 1.210(4) . ? N76 O77 1.229(4) . ? N79 O80 1.224(4) . ? N79 O81 1.235(4) . ? N82 C83 1.421(4) . ? C83 C84 1.3900 . ? C83 C88 1.3900 . ? C84 C85 1.3900 . ? C85 C86 1.3900 . ? C86 C87 1.3900 . ? C87 C88 1.3900 . ? C88 O89 1.359(5) . ? O89 C90 1.429(5) . ? 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 C3 O2 C1 118.1(5) . . ? O2 C3 C4 126.4(3) . . ? O2 C3 C8 113.5(3) . . ? C4 C3 C8 120.0 . . ? C3 C4 C5 120.0 . . ? C6 C5 C4 120.0 . . ? C5 C6 C7 120.0 . . ? C6 C7 C8 120.0 . . ? C7 C8 C3 120.0 . . ? C7 C8 N9 123.5(3) . . ? C3 C8 N9 116.3(3) . . ? C10 N9 C8 130.6(3) . . ? N9 C10 C11 120.1(2) . . ? N9 C10 C15 119.9(2) . . ? C11 C10 C15 120.0 . . ? C10 C11 C12 120.0 . . ? N22 C12 C13 119.5(2) . . ? N22 C12 C11 120.5(2) . . ? C13 C12 C11 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 N16 125.4(3) . . ? C14 C13 N16 114.6(3) . . ? C15 C14 C13 120.0 . . ? C14 C15 C10 120.0 . . ? C14 C15 N19 115.1(3) . . ? C10 C15 N19 124.9(3) . . ? O18 N16 O17 122.5(3) . . ? O18 N16 C13 119.2(4) . . ? O17 N16 C13 118.2(4) . . ? O21 N19 O20 121.2(4) . . ? O21 N19 C15 119.1(4) . . ? O20 N19 C15 119.7(4) . . ? C12 N22 C23 131.1(3) . . ? C24 C23 C28 120.0 . . ? C24 C23 N22 115.6(2) . . ? C28 C23 N22 124.2(2) . . ? O29 C24 C25 123.3(3) . . ? O29 C24 C23 116.6(3) . . ? C25 C24 C23 120.0 . . ? C24 C25 C26 120.0 . . ? O34 C26 C25 124.0(3) . . ? O34 C26 C27 116.0(3) . . ? C25 C26 C27 120.0 . . ? C28 C27 C26 120.0 . . ? C28 C27 N39 120.3(3) . . ? C26 C27 N39 119.5(3) . . ? C27 C28 C23 120.0 . . ? C24 O29 C30 119.6(3) . . ? O29 C30 C31 106.9(4) . . ? C30 C31 C33 109.6(5) . . ? C30 C31 C32 104.3(5) . . ? C33 C31 C32 112.9(5) . . ? C26 O34 C35 116.5(3) . . ? O34 C35 C36 107.3(4) . . ? C38 C36 C38' 96.4(9) . . ? C38 C36 C35 115.2(7) . . ? C38' C36 C35 109.3(6) . . ? C38 C36 C37 117.9(6) . . ? C38' C36 C37 109.9(8) . . ? C35 C36 C37 107.5(5) . . ? C40 N39 C27 120.3(3) . . ? C41 C40 C45 120.0 . . ? C41 C40 N39 123.2(2) . . ? C45 C40 N39 116.8(2) . . ? C40 C41 C42 120.0 . . ? C40 C41 N46 125.1(3) . . ? C42 C41 N46 114.9(3) . . ? C43 C42 C41 120.0 . . ? C44 C43 C42 120.0 . . ? C44 C43 N49 124.9(3) . . ? C42 C43 N49 115.1(3) . . ? N52 C44 C43 122.8(2) . . ? N52 C44 C45 117.2(2) . . ? C43 C44 C45 120.0 . . ? C44 C45 C40 120.0 . . ? O48 N46 O47 120.4(4) . . ? O48 N46 C41 121.7(4) . . ? O47 N46 C41 117.9(4) . . ? O51 N49 O50 119.2(4) . . ? O51 N49 C43 122.8(4) . . ? O50 N49 C43 117.9(4) . . ? C44 N52 C53 124.5(3) . . ? C54 C53 C58 120.0 . . ? C54 C53 N52 119.9(2) . . ? C58 C53 N52 120.1(2) . . ? O59 C54 C55 123.9(2) . . ? O59 C54 C53 116.1(2) . . ? C55 C54 C53 120.0 . . ? C54 C55 C56 120.0 . . ? O64 C56 C57 115.4(2) . . ? O64 C56 C55 124.6(2) . . ? C57 C56 C55 120.0 . . ? C58 C57 C56 120.0 . . ? C58 C57 N69 123.3(2) . . ? C56 C57 N69 116.6(2) . . ? C57 C58 C53 120.0 . . ? C54 O59 C60 117.8(3) . . ? O59 C60 C61' 110.6(8) . . ? O59 C60 C61 108.3(6) . . ? C61' C60 C61 5.3(14) . . ? C62 C61 C63 110.1(16) . . ? C62 C61 C60 104.0(11) . . ? C63 C61 C60 108.6(12) . . ? C60 C61' C63' 108.0(14) . . ? C60 C61' C62' 112.2(14) . . ? C63' C61' C62' 104.5(13) . . ? C56 O64 C65 118.0(3) . . ? O64 C65 C66 107.4(3) . . ? C67 C66 C65 112.2(4) . . ? C67 C66 C68 112.9(6) . . ? C65 C66 C68 105.7(4) . . ? C70 N69 C57 129.9(2) . . ? N69 C70 C71 120.3(2) . . ? N69 C70 C75 119.7(2) . . ? C71 C70 C75 120.0 . . ? C70 C71 C72 120.0 . . ? C70 C71 N76 125.0(3) . . ? C72 C71 N76 115.0(3) . . ? C73 C72 C71 120.0 . . ? C72 C73 C74 120.0 . . ? C72 C73 N79 115.0(3) . . ? C74 C73 N79 125.0(3) . . ? C73 C74 C75 120.0 . . ? C73 C74 N82 119.8(2) . . ? C75 C74 N82 120.2(2) . . ? C74 C75 C70 120.0 . . ? O78 N76 O77 121.6(4) . . ? O78 N76 C71 119.8(4) . . ? O77 N76 C71 118.5(4) . . ? O80 N79 O81 121.1(4) . . ? O80 N79 C73 119.0(4) . . ? O81 N79 C73 119.9(4) . . ? C74 N82 C83 129.7(3) . . ? C84 C83 C88 120.0 . . ? C84 C83 N82 124.9(3) . . ? C88 C83 N82 115.1(3) . . ? C83 C84 C85 120.0 . . ? C84 C85 C86 120.0 . . ? C87 C86 C85 120.0 . . ? C88 C87 C86 120.0 . . ? O89 C88 C87 124.2(3) . . ? O89 C88 C83 115.7(3) . . ? C87 C88 C83 120.0 . . ? C88 O89 C90 118.4(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 C1 O2 C3 C4 -4.2(6) . . . . ? C1 O2 C3 C8 171.6(3) . . . . ? O2 C3 C4 C5 175.6(4) . . . . ? C8 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C7 0.0 . . . . ? C5 C6 C7 C8 0.0 . . . . ? C6 C7 C8 C3 0.0 . . . . ? C6 C7 C8 N9 -175.2(3) . . . . ? O2 C3 C8 C7 -176.1(4) . . . . ? C4 C3 C8 C7 0.0 . . . . ? O2 C3 C8 N9 -0.6(3) . . . . ? C4 C3 C8 N9 175.6(3) . . . . ? C7 C8 N9 C10 -24.3(5) . . . . ? C3 C8 N9 C10 160.3(3) . . . . ? C8 N9 C10 C11 -17.1(5) . . . . ? C8 N9 C10 C15 163.1(3) . . . . ? N9 C10 C11 C12 -179.8(3) . . . . ? C15 C10 C11 C12 0.0 . . . . ? C10 C11 C12 N22 -179.9(3) . . . . ? C10 C11 C12 C13 0.0 . . . . ? N22 C12 C13 C14 179.9(3) . . . . ? C11 C12 C13 C14 0.0 . . . . ? N22 C12 C13 N16 -0.2(3) . . . . ? C11 C12 C13 N16 179.9(3) . . . . ? C12 C13 C14 C15 0.0 . . . . ? N16 C13 C14 C15 -179.9(3) . . . . ? C13 C14 C15 C10 0.0 . . . . ? C13 C14 C15 N19 179.7(3) . . . . ? N9 C10 C15 C14 179.8(3) . . . . ? C11 C10 C15 C14 0.0 . . . . ? N9 C10 C15 N19 0.2(4) . . . . ? C11 C10 C15 N19 -179.6(3) . . . . ? C12 C13 N16 O18 172.9(3) . . . . ? C14 C13 N16 O18 -7.2(4) . . . . ? C12 C13 N16 O17 -5.3(5) . . . . ? C14 C13 N16 O17 174.6(3) . . . . ? C14 C15 N19 O21 12.5(5) . . . . ? C10 C15 N19 O21 -167.9(4) . . . . ? C14 C15 N19 O20 -168.1(4) . . . . ? C10 C15 N19 O20 11.5(6) . . . . ? C13 C12 N22 C23 -173.9(3) . . . . ? C11 C12 N22 C23 6.0(4) . . . . ? C12 N22 C23 C24 -153.7(3) . . . . ? C12 N22 C23 C28 31.0(4) . . . . ? C28 C23 C24 O29 177.7(3) . . . . ? N22 C23 C24 O29 2.2(3) . . . . ? C28 C23 C24 C25 0.0 . . . . ? N22 C23 C24 C25 -175.5(2) . . . . ? O29 C24 C25 C26 -177.5(3) . . . . ? C23 C24 C25 C26 0.0 . . . . ? C24 C25 C26 O34 -177.4(3) . . . . ? C24 C25 C26 C27 0.0 . . . . ? O34 C26 C27 C28 177.6(2) . . . . ? C25 C26 C27 C28 0.0 . . . . ? O34 C26 C27 N39 3.4(3) . . . . ? C25 C26 C27 N39 -174.1(2) . . . . ? C26 C27 C28 C23 0.0 . . . . ? N39 C27 C28 C23 174.1(3) . . . . ? C24 C23 C28 C27 0.0 . . . . ? N22 C23 C28 C27 175.1(3) . . . . ? C25 C24 O29 C30 -4.4(4) . . . . ? C23 C24 O29 C30 178.0(3) . . . . ? C24 O29 C30 C31 178.4(4) . . . . ? O29 C30 C31 C33 -62.7(5) . . . . ? O29 C30 C31 C32 176.2(4) . . . . ? C25 C26 O34 C35 12.6(4) . . . . ? C27 C26 O34 C35 -164.9(3) . . . . ? C26 O34 C35 C36 174.0(4) . . . . ? O34 C35 C36 C38 51.2(7) . . . . ? O34 C35 C36 C38' -56.0(9) . . . . ? O34 C35 C36 C37 -175.2(5) . . . . ? C28 C27 N39 C40 -101.2(3) . . . . ? C26 C27 N39 C40 72.9(3) . . . . ? C27 N39 C40 C41 -178.5(2) . . . . ? C27 N39 C40 C45 2.5(4) . . . . ? C45 C40 C41 C42 0.0 . . . . ? N39 C40 C41 C42 -178.9(3) . . . . ? C45 C40 C41 N46 -176.7(3) . . . . ? N39 C40 C41 N46 4.4(3) . . . . ? C40 C41 C42 C43 0.0 . . . . ? N46 C41 C42 C43 177.0(2) . . . . ? C41 C42 C43 C44 0.0 . . . . ? C41 C42 C43 N49 179.4(2) . . . . ? C42 C43 C44 N52 -177.8(3) . . . . ? N49 C43 C44 N52 2.9(3) . . . . ? C42 C43 C44 C45 0.0 . . . . ? N49 C43 C44 C45 -179.3(3) . . . . ? N52 C44 C45 C40 178.0(3) . . . . ? C43 C44 C45 C40 0.0 . . . . ? C41 C40 C45 C44 0.0 . . . . ? N39 C40 C45 C44 179.0(2) . . . . ? C40 C41 N46 O48 172.6(3) . . . . ? C42 C41 N46 O48 -4.3(4) . . . . ? C40 C41 N46 O47 -6.8(5) . . . . ? C42 C41 N46 O47 176.3(3) . . . . ? C44 C43 N49 O51 -178.9(3) . . . . ? C42 C43 N49 O51 1.7(4) . . . . ? C44 C43 N49 O50 1.5(5) . . . . ? C42 C43 N49 O50 -177.9(3) . . . . ? C43 C44 N52 C53 176.6(2) . . . . ? C45 C44 N52 C53 -1.3(4) . . . . ? C44 N52 C53 C54 -115.2(3) . . . . ? C44 N52 C53 C58 65.0(4) . . . . ? C58 C53 C54 O59 -178.8(2) . . . . ? N52 C53 C54 O59 1.4(3) . . . . ? C58 C53 C54 C55 0.0 . . . . ? N52 C53 C54 C55 -179.8(3) . . . . ? O59 C54 C55 C56 178.7(3) . . . . ? C53 C54 C55 C56 0.0 . . . . ? C54 C55 C56 O64 179.6(2) . . . . ? C54 C55 C56 C57 0.0 . . . . ? O64 C56 C57 C58 -179.7(2) . . . . ? C55 C56 C57 C58 0.0 . . . . ? O64 C56 C57 N69 1.9(3) . . . . ? C55 C56 C57 N69 -178.4(2) . . . . ? C56 C57 C58 C53 0.0 . . . . ? N69 C57 C58 C53 178.3(3) . . . . ? C54 C53 C58 C57 0.0 . . . . ? N52 C53 C58 C57 179.8(3) . . . . ? C55 C54 O59 C60 -3.7(4) . . . . ? C53 C54 O59 C60 175.0(2) . . . . ? C54 O59 C60 C61' -173.2(9) . . . . ? C54 O59 C60 C61 -178.3(9) . . . . ? O59 C60 C61 C62 51.9(12) . . . . ? C61' C60 C61 C62 -65(15) . . . . ? O59 C60 C61 C63 169.2(14) . . . . ? C61' C60 C61 C63 53(15) . . . . ? O59 C60 C61' C63' -173.9(13) . . . . ? C61 C60 C61' C63' -109(15) . . . . ? O59 C60 C61' C62' -59.2(15) . . . . ? C61 C60 C61' C62' 6(14) . . . . ? C57 C56 O64 C65 -177.7(3) . . . . ? C55 C56 O64 C65 2.7(4) . . . . ? C56 O64 C65 C66 -174.7(4) . . . . ? O64 C65 C66 C67 61.8(6) . . . . ? O64 C65 C66 C68 -174.8(6) . . . . ? C58 C57 N69 C70 37.8(4) . . . . ? C56 C57 N69 C70 -143.9(3) . . . . ? C57 N69 C70 C71 -179.5(3) . . . . ? C57 N69 C70 C75 0.8(4) . . . . ? N69 C70 C71 C72 -179.7(3) . . . . ? C75 C70 C71 C72 0.0 . . . . ? N69 C70 C71 N76 -1.8(3) . . . . ? C75 C70 C71 N76 178.0(3) . . . . ? C70 C71 C72 C73 0.0 . . . . ? N76 C71 C72 C73 -178.2(3) . . . . ? C71 C72 C73 C74 0.0 . . . . ? C71 C72 C73 N79 179.0(3) . . . . ? C72 C73 C74 C75 0.0 . . . . ? N79 C73 C74 C75 -178.9(3) . . . . ? C72 C73 C74 N82 -179.8(3) . . . . ? N79 C73 C74 N82 1.3(4) . . . . ? C73 C74 C75 C70 0.0 . . . . ? N82 C74 C75 C70 179.8(3) . . . . ? N69 C70 C75 C74 179.7(3) . . . . ? C71 C70 C75 C74 0.0 . . . . ? C70 C71 N76 O78 176.5(3) . . . . ? C72 C71 N76 O78 -5.5(5) . . . . ? C70 C71 N76 O77 -6.4(5) . . . . ? C72 C71 N76 O77 171.6(3) . . . . ? C72 C73 N79 O80 8.7(6) . . . . ? C74 C73 N79 O80 -172.4(4) . . . . ? C72 C73 N79 O81 -171.1(4) . . . . ? C74 C73 N79 O81 7.8(6) . . . . ? C73 C74 N82 C83 164.6(3) . . . . ? C75 C74 N82 C83 -15.2(5) . . . . ? C74 N82 C83 C84 -20.4(5) . . . . ? C74 N82 C83 C88 161.8(3) . . . . ? C88 C83 C84 C85 0.0 . . . . ? N82 C83 C84 C85 -177.7(3) . . . . ? C83 C84 C85 C86 0.0 . . . . ? C84 C85 C86 C87 0.0 . . . . ? C85 C86 C87 C88 0.0 . . . . ? C86 C87 C88 O89 176.0(4) . . . . ? C86 C87 C88 C83 0.0 . . . . ? C84 C83 C88 O89 -176.4(3) . . . . ? N82 C83 C88 O89 1.6(3) . . . . ? C84 C83 C88 C87 0.0 . . . . ? N82 C83 C88 C87 177.9(3) . . . . ? C87 C88 O89 C90 -14.9(5) . . . . ? C83 C88 O89 C90 161.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 72.45 _diffrn_measured_fraction_theta_full 0.940 _refine_diff_density_max 0.216 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.041 _vrf_PLAT242 ; PROBLEM: Check Low Ueq as Compared to Neighbors for C66 RESPONSE: disorders on lateral chains ; _vrf_PLAT413 ; PROBLEM: Short Inter XH3 .. XHn H38F .. H68A .. 1.81 Ang. RESPONSE: statistical occupancy explain this short distance ; _vrf_PLAT026 ; PROBLEM: Ratio Observed / Unique Reflections too Low .... 39 Perc. RESPONSE : diffraction of the best crystal was too low ; _vrf_PLAT220 ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.79 Ratio RESPONSE: atomic species identification has been checked ; #====END data_vm164 _database_code_depnum_ccdc_archive 'CCDC 740015' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H14 N4 O4' _chemical_formula_weight 350.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.952(6) _cell_length_b 11.007(3) _cell_length_c 14.736(5) _cell_angle_alpha 90.00 _cell_angle_beta 109.90(3) _cell_angle_gamma 90.00 _cell_volume 1670.3(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25.0 _cell_measurement_theta_max 35.0 _exptl_crystal_description block _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.847 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.8489 _exptl_absorpt_correction_T_max 0.8835 _exptl_absorpt_process_details '(North et al., 1968)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius cad-4 diffractometer' _diffrn_measurement_method \W-2\Scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% ? _diffrn_reflns_number 3100 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0111 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.29 _diffrn_reflns_theta_max 69.06 _reflns_number_total 3100 _reflns_number_gt 2635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4/PC v1.5c July 1994' _computing_cell_refinement 'CAD4/PC v1.5c July 1994' _computing_data_reduction 'CAD4/PC v1.5c July 1994' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.3240P] 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 SHELXL _refine_ls_extinction_coef 0.055(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3100 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1154 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 0.24733(13) 0.84702(13) 0.80578(10) 0.0470(3) Uani 1 1 d . . . C2 C 0.23084(17) 0.95745(15) 0.75877(12) 0.0632(4) Uani 1 1 d . . . H2 H 0.2996 1.0119 0.7719 0.076 Uiso 1 1 calc R . . C3 C 0.1114(2) 0.98631(19) 0.69205(16) 0.0897(7) Uani 1 1 d . . . H3 H 0.0998 1.0607 0.6603 0.108 Uiso 1 1 calc R . . C4 C 0.0099(2) 0.9064(2) 0.67213(17) 0.0954(8) Uani 1 1 d . . . H4 H -0.0699 0.9259 0.6262 0.114 Uiso 1 1 calc R . . C5 C 0.02608(17) 0.7974(2) 0.72009(16) 0.0812(6) Uani 1 1 d . . . H5 H -0.0432 0.7435 0.7070 0.097 Uiso 1 1 calc R . . C6 C 0.14461(15) 0.76725(16) 0.78760(13) 0.0611(4) Uani 1 1 d . . . H6 H 0.1551 0.6938 0.8205 0.073 Uiso 1 1 calc R . . N7 N 0.37034(11) 0.82344(11) 0.87715(9) 0.0507(3) Uani 1 1 d . . . H7 H 0.4035 0.8812 0.9173 0.061 Uiso 1 1 calc R . . C8 C 0.44099(12) 0.71995(12) 0.88870(10) 0.0430(3) Uani 1 1 d . . . C9 C 0.40516(13) 0.62510(13) 0.82171(10) 0.0464(3) Uani 1 1 d . . . H9 H 0.3309 0.6350 0.7678 0.056 Uiso 1 1 calc R . . C10 C 0.47394(13) 0.51642(12) 0.83078(10) 0.0460(3) Uani 1 1 d . . . C11 C 0.58922(14) 0.50463(12) 0.91360(10) 0.0471(3) Uani 1 1 d . . . C12 C 0.62708(13) 0.59682(12) 0.98027(10) 0.0456(3) Uani 1 1 d . . . H12 H 0.7022 0.5874 1.0336 0.055 Uiso 1 1 calc R . . C13 C 0.55682(13) 0.70251(12) 0.97027(10) 0.0429(3) Uani 1 1 d . . . N14 N 0.60551(11) 0.79005(11) 1.04684(8) 0.0479(3) Uani 1 1 d . . . O15 O 0.55147(11) 0.88969(10) 1.03998(8) 0.0641(3) Uani 1 1 d . . . O16 O 0.69934(12) 0.76305(11) 1.11783(8) 0.0694(4) Uani 1 1 d . . . N17 N 0.66974(14) 0.39730(11) 0.93433(10) 0.0580(4) Uani 1 1 d . . . O18 O 0.63011(14) 0.30476(10) 0.88562(10) 0.0780(4) Uani 1 1 d . . . O19 O 0.77450(13) 0.39988(12) 1.00024(10) 0.0807(4) Uani 1 1 d . . . N20 N 0.43421(13) 0.42538(12) 0.76472(10) 0.0564(4) Uani 1 1 d . . . H20 H 0.4798 0.3599 0.7776 0.068 Uiso 1 1 calc R . . C21 C 0.32682(15) 0.42514(14) 0.67716(11) 0.0518(4) Uani 1 1 d . . . C22 C 0.30569(19) 0.51770(16) 0.61054(12) 0.0645(5) Uani 1 1 d . . . H22 H 0.3600 0.5852 0.6238 0.077 Uiso 1 1 calc R . . C23 C 0.2040(2) 0.51012(19) 0.52425(13) 0.0759(5) Uani 1 1 d . . . H23 H 0.1889 0.5735 0.4801 0.091 Uiso 1 1 calc R . . C24 C 0.1247(2) 0.4098(2) 0.50297(14) 0.0795(6) Uani 1 1 d . . . H24 H 0.0564 0.4050 0.4446 0.095 Uiso 1 1 calc R . . C25 C 0.1470(2) 0.3168(2) 0.56847(16) 0.0832(6) Uani 1 1 d . . . H25 H 0.0941 0.2483 0.5539 0.100 Uiso 1 1 calc R . . C26 C 0.24715(19) 0.32370(16) 0.65564(13) 0.0683(5) Uani 1 1 d . . . H26 H 0.2612 0.2605 0.6999 0.082 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 0.0432(7) 0.0465(8) 0.0448(7) -0.0083(6) 0.0067(6) 0.0059(6) C2 0.0610(10) 0.0485(9) 0.0669(10) -0.0022(7) 0.0044(8) 0.0021(7) C3 0.0838(14) 0.0648(12) 0.0896(14) 0.0133(10) -0.0106(11) 0.0139(10) C4 0.0621(12) 0.0936(16) 0.0939(15) -0.0010(12) -0.0209(10) 0.0159(11) C5 0.0469(9) 0.0859(14) 0.0935(14) -0.0086(11) 0.0012(9) -0.0033(9) C6 0.0488(8) 0.0602(10) 0.0670(10) -0.0011(8) 0.0101(7) -0.0004(7) N7 0.0454(6) 0.0420(6) 0.0540(7) -0.0097(5) 0.0030(5) 0.0039(5) C8 0.0392(7) 0.0396(7) 0.0489(7) -0.0008(6) 0.0133(6) -0.0011(5) C9 0.0438(7) 0.0426(7) 0.0485(7) -0.0036(6) 0.0102(6) -0.0006(6) C10 0.0504(8) 0.0380(7) 0.0515(8) -0.0018(6) 0.0199(6) -0.0036(6) C11 0.0493(8) 0.0375(7) 0.0558(8) 0.0056(6) 0.0195(6) 0.0039(6) C12 0.0413(7) 0.0439(8) 0.0492(7) 0.0050(6) 0.0124(6) 0.0005(5) C13 0.0399(7) 0.0396(7) 0.0467(7) -0.0016(5) 0.0113(6) -0.0037(5) N14 0.0446(6) 0.0449(7) 0.0486(7) -0.0020(5) 0.0086(5) -0.0039(5) O15 0.0594(7) 0.0457(6) 0.0706(7) -0.0153(5) 0.0004(5) 0.0043(5) O16 0.0678(7) 0.0644(7) 0.0541(6) -0.0044(5) -0.0075(5) 0.0055(6) N17 0.0664(9) 0.0430(7) 0.0660(8) 0.0069(6) 0.0241(7) 0.0099(6) O18 0.0921(9) 0.0396(6) 0.0951(9) -0.0040(6) 0.0224(8) 0.0127(6) O19 0.0740(8) 0.0676(8) 0.0833(9) 0.0045(7) 0.0044(7) 0.0270(6) N20 0.0645(8) 0.0385(6) 0.0621(8) -0.0080(6) 0.0163(6) 0.0007(5) C21 0.0615(9) 0.0434(8) 0.0532(8) -0.0111(6) 0.0232(7) -0.0036(6) C22 0.0849(12) 0.0526(9) 0.0618(10) -0.0029(7) 0.0324(9) -0.0101(8) C23 0.0992(14) 0.0741(12) 0.0565(10) 0.0049(9) 0.0293(10) 0.0090(11) C24 0.0776(12) 0.0919(15) 0.0608(10) -0.0144(10) 0.0128(9) 0.0060(11) C25 0.0836(13) 0.0740(13) 0.0809(13) -0.0171(11) 0.0137(11) -0.0228(11) C26 0.0826(12) 0.0506(9) 0.0666(11) -0.0055(8) 0.0188(9) -0.0146(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.380(2) . ? C1 C2 1.380(2) . ? C1 N7 1.4227(18) . ? C2 C3 1.380(2) . ? C3 C4 1.369(3) . ? C4 C5 1.373(3) . ? C5 C6 1.380(2) . ? N7 C8 1.3549(17) . ? C8 C9 1.3981(19) . ? C8 C13 1.433(2) . ? C9 C10 1.396(2) . ? C10 N20 1.3612(18) . ? C10 C11 1.432(2) . ? C11 C12 1.375(2) . ? C11 N17 1.4433(18) . ? C12 C13 1.3748(19) . ? C13 N14 1.4410(18) . ? N14 O16 1.2275(16) . ? N14 O15 1.2340(16) . ? N17 O19 1.2255(19) . ? N17 O18 1.2366(18) . ? N20 C21 1.420(2) . ? C21 C22 1.379(2) . ? C21 C26 1.386(2) . ? C22 C23 1.379(3) . ? C23 C24 1.374(3) . ? C24 C25 1.371(3) . ? C25 C26 1.378(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 120.28(14) . . ? C6 C1 N7 122.13(14) . . ? C2 C1 N7 117.45(13) . . ? C3 C2 C1 119.40(17) . . ? C4 C3 C2 120.59(19) . . ? C3 C4 C5 119.85(18) . . ? C6 C5 C4 120.41(19) . . ? C1 C6 C5 119.45(17) . . ? C8 N7 C1 127.07(12) . . ? N7 C8 C9 121.88(13) . . ? N7 C8 C13 121.51(12) . . ? C9 C8 C13 116.61(12) . . ? C10 C9 C8 124.04(13) . . ? N20 C10 C9 122.12(14) . . ? N20 C10 C11 121.14(13) . . ? C9 C10 C11 116.73(12) . . ? C12 C11 C10 120.40(13) . . ? C12 C11 N17 116.04(13) . . ? C10 C11 N17 123.54(13) . . ? C13 C12 C11 121.76(13) . . ? C12 C13 C8 120.44(13) . . ? C12 C13 N14 115.94(12) . . ? C8 C13 N14 123.60(12) . . ? O16 N14 O15 121.61(12) . . ? O16 N14 C13 118.99(12) . . ? O15 N14 C13 119.39(12) . . ? O19 N17 O18 121.87(13) . . ? O19 N17 C11 119.25(13) . . ? O18 N17 C11 118.88(14) . . ? C10 N20 C21 128.00(13) . . ? C22 C21 C26 119.51(16) . . ? C22 C21 N20 122.16(14) . . ? C26 C21 N20 118.15(15) . . ? C23 C22 C21 119.94(17) . . ? C24 C23 C22 120.58(18) . . ? C23 C24 C25 119.49(19) . . ? C24 C25 C26 120.65(19) . . ? C25 C26 C21 119.81(18) . . ? 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 -1.3(3) . . . . ? N7 C1 C2 C3 -177.18(17) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C2 C1 C6 C5 1.7(3) . . . . ? N7 C1 C6 C5 177.44(16) . . . . ? C4 C5 C6 C1 -0.7(3) . . . . ? C6 C1 N7 C8 49.6(2) . . . . ? C2 C1 N7 C8 -134.60(16) . . . . ? C1 N7 C8 C9 7.5(2) . . . . ? C1 N7 C8 C13 -172.76(13) . . . . ? N7 C8 C9 C10 -179.40(13) . . . . ? C13 C8 C9 C10 0.9(2) . . . . ? C8 C9 C10 N20 178.71(14) . . . . ? C8 C9 C10 C11 -1.2(2) . . . . ? N20 C10 C11 C12 -179.17(13) . . . . ? C9 C10 C11 C12 0.7(2) . . . . ? N20 C10 C11 N17 -1.0(2) . . . . ? C9 C10 C11 N17 178.85(13) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? N17 C11 C12 C13 -178.26(12) . . . . ? C11 C12 C13 C8 -0.3(2) . . . . ? C11 C12 C13 N14 178.27(12) . . . . ? N7 C8 C13 C12 -179.82(13) . . . . ? C9 C8 C13 C12 -0.07(19) . . . . ? N7 C8 C13 N14 1.7(2) . . . . ? C9 C8 C13 N14 -178.57(13) . . . . ? C12 C13 N14 O16 -4.64(19) . . . . ? C8 C13 N14 O16 173.93(13) . . . . ? C12 C13 N14 O15 175.97(13) . . . . ? C8 C13 N14 O15 -5.5(2) . . . . ? C12 C11 N17 O19 -10.3(2) . . . . ? C10 C11 N17 O19 171.46(14) . . . . ? C12 C11 N17 O18 168.83(14) . . . . ? C10 C11 N17 O18 -9.4(2) . . . . ? C9 C10 N20 C21 3.5(2) . . . . ? C11 C10 N20 C21 -176.64(14) . . . . ? C10 N20 C21 C22 50.2(2) . . . . ? C10 N20 C21 C26 -134.79(17) . . . . ? C26 C21 C22 C23 1.5(3) . . . . ? N20 C21 C22 C23 176.51(15) . . . . ? C21 C22 C23 C24 -1.4(3) . . . . ? C22 C23 C24 C25 0.2(3) . . . . ? C23 C24 C25 C26 0.7(3) . . . . ? C24 C25 C26 C21 -0.5(3) . . . . ? C22 C21 C26 C25 -0.6(3) . . . . ? N20 C21 C26 C25 -175.77(17) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 69.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.256 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.041 #====END