# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email r.c.f.jones@lboro.ac.uk _publ_contact_author_name R.Jones loop_ _publ_author_name R.Jones 'James Iley' 'Maria Sanchis-Amat' 'Xiaohui Zhang' V.McKee 'Simon Coles' 'Thomas Gelbrich' data_rcfjdl2 _database_code_depnum_ccdc_archive 'CCDC 823959' #TrackingRef '- Fig1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 N4 O4' _chemical_formula_weight 382.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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)/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 6.561(3) _cell_length_b 9.171(4) _cell_length_c 32.072(13) _cell_angle_alpha 90.00 _cell_angle_beta 94.608(6) _cell_angle_gamma 90.00 _cell_volume 1923.4(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1284 _cell_measurement_theta_min 3.71 _cell_measurement_theta_max 25.21 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.84640 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 16.2SMX' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker APEX II CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6398 _diffrn_reflns_av_R_equivalents 0.1271 _diffrn_reflns_av_sigmaI/netI 0.0882 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.71 _diffrn_reflns_theta_max 22.50 _reflns_number_total 1480 _reflns_number_gt 1105 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX II' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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. The data set is very weak with no significant diffraction beyond 1 Angstrom for this reason the data set has been truncated at 45 degrees. ; _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^)+(0.0807P)^2^+7.0827P] 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 0.009(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1480 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1062 _refine_ls_R_factor_gt 0.0834 _refine_ls_wR_factor_ref 0.2177 _refine_ls_wR_factor_gt 0.2070 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _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 0.0941(13) 0.6779(9) 0.6005(3) 0.033(3) Uani 1 1 d . . . H1 H -0.0480 0.7181 0.5979 0.040 Uiso 1 1 calc R . . N1 N 0.1702(11) 0.6732(8) 0.6440(3) 0.040(2) Uani 1 1 d . . . C2 C 0.2966(15) 0.8026(11) 0.6508(3) 0.051(3) Uani 1 1 d . . . H2A H 0.3962 0.7909 0.6754 0.061 Uiso 1 1 calc R . . H2B H 0.2121 0.8903 0.6546 0.061 Uiso 1 1 calc R . . C3 C 0.4044(15) 0.8113(10) 0.6102(3) 0.051(3) Uani 1 1 d . . . H3A H 0.4588 0.9102 0.6056 0.061 Uiso 1 1 calc R . . H3B H 0.5166 0.7392 0.6098 0.061 Uiso 1 1 calc R . . N2 N 0.2310(10) 0.7749(7) 0.5790(2) 0.032(2) Uani 1 1 d . . . C4 C 0.2769(13) 0.7093(9) 0.5396(3) 0.031(2) Uani 1 1 d . . . C5 C 0.1077(17) 0.7561(9) 0.5079(3) 0.030(2) Uani 1 1 d . . . O1 O -0.0734(10) 0.7292(6) 0.50869(19) 0.0408(19) Uani 1 1 d . . . N3 N 0.1878(12) 0.8383(7) 0.4774(2) 0.028(2) Uani 1 1 d . . . C6 C 0.0676(14) 0.9058(10) 0.4433(3) 0.043(3) Uani 1 1 d . . . H6A H 0.0816 0.8501 0.4176 0.064 Uiso 1 1 calc R . . H6B H 0.1156 1.0058 0.4396 0.064 Uiso 1 1 calc R . . H6C H -0.0764 0.9075 0.4494 0.064 Uiso 1 1 calc R . . C7 C 0.4001(16) 0.8394(9) 0.4824(3) 0.032(3) Uani 1 1 d . . . O2 O 0.5018(9) 0.9011(7) 0.4577(2) 0.0435(19) Uani 1 1 d . . . C8 C 0.4703(13) 0.7640(9) 0.5213(3) 0.035(3) Uani 1 1 d . . . H8A H 0.5461 0.8318 0.5410 0.042 Uiso 1 1 calc R . . H8B H 0.5610 0.6814 0.5155 0.042 Uiso 1 1 calc R . . C9 C 0.2554(12) 0.5408(9) 0.5468(3) 0.032(3) Uani 1 1 d . . . H9 H 0.2080 0.4910 0.5200 0.038 Uiso 1 1 calc R . . C10 C 0.4401(15) 0.4673(9) 0.5667(3) 0.029(2) Uani 1 1 d . . . O3 O 0.6126(10) 0.4622(6) 0.5554(2) 0.0405(18) Uani 1 1 d . . . N4 N 0.3876(12) 0.3945(8) 0.6020(3) 0.035(2) Uani 1 1 d . . . C11 C 0.5234(15) 0.3020(10) 0.6276(3) 0.049(3) Uani 1 1 d . . . H11A H 0.4728 0.2923 0.6554 0.074 Uiso 1 1 calc R . . H11B H 0.6605 0.3452 0.6303 0.074 Uiso 1 1 calc R . . H11C H 0.5294 0.2056 0.6146 0.074 Uiso 1 1 calc R . . C12 C 0.1818(15) 0.4126(10) 0.6081(3) 0.033(3) Uani 1 1 d . . . O4 O 0.0964(10) 0.3449(7) 0.6338(2) 0.049(2) Uani 1 1 d . . . C13 C 0.0975(12) 0.5259(10) 0.5781(3) 0.032(2) Uani 1 1 d . . . H13 H -0.0397 0.4983 0.5646 0.039 Uiso 1 1 calc R . . C14 C 0.0192(15) 0.6572(11) 0.6735(3) 0.054(3) Uani 1 1 d . . . H14A H -0.0765 0.5784 0.6639 0.064 Uiso 1 1 calc R . . H14B H -0.0603 0.7487 0.6744 0.064 Uiso 1 1 calc R . . C15 C 0.1093(17) 0.6221(11) 0.7170(3) 0.048(3) Uani 1 1 d . . . C16 C 0.2839(19) 0.5360(12) 0.7229(4) 0.064(3) Uani 1 1 d . . . H16 H 0.3458 0.4999 0.6992 0.076 Uiso 1 1 calc R . . C17 C 0.368(2) 0.5026(12) 0.7618(5) 0.076(4) Uani 1 1 d . . . H17 H 0.4908 0.4475 0.7649 0.091 Uiso 1 1 calc R . . C18 C 0.278(2) 0.5470(14) 0.7967(4) 0.078(4) Uani 1 1 d . . . H18 H 0.3345 0.5198 0.8238 0.094 Uiso 1 1 calc R . . C19 C 0.107(3) 0.6311(14) 0.7917(4) 0.081(4) Uani 1 1 d . . . H19 H 0.0428 0.6628 0.8157 0.098 Uiso 1 1 calc R . . C20 C 0.024(2) 0.6713(13) 0.7520(4) 0.079(4) Uani 1 1 d . . . H20 H -0.0924 0.7333 0.7491 0.095 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 0.017(5) 0.035(6) 0.051(8) -0.006(6) 0.015(5) 0.004(5) N1 0.042(5) 0.036(5) 0.045(6) -0.007(4) 0.012(5) 0.004(4) C2 0.056(7) 0.043(7) 0.054(8) -0.008(6) 0.004(6) 0.008(6) C3 0.062(7) 0.034(6) 0.056(7) -0.007(5) -0.002(6) -0.002(5) N2 0.020(5) 0.025(5) 0.052(5) -0.003(4) 0.010(4) 0.002(4) C4 0.022(6) 0.024(6) 0.048(7) -0.008(5) 0.007(6) 0.003(5) C5 0.026(8) 0.024(6) 0.042(7) -0.002(5) 0.014(6) -0.003(5) O1 0.013(4) 0.044(4) 0.066(5) 0.003(3) 0.007(3) -0.001(3) N3 0.016(6) 0.026(5) 0.042(5) 0.003(4) 0.004(4) 0.003(4) C6 0.049(7) 0.030(6) 0.049(7) 0.006(5) -0.001(6) 0.000(5) C7 0.029(8) 0.014(6) 0.054(8) -0.009(6) 0.014(6) 0.004(5) O2 0.034(4) 0.042(4) 0.057(5) 0.000(4) 0.014(4) -0.005(3) C8 0.028(6) 0.027(6) 0.050(7) 0.004(5) 0.008(5) -0.009(5) C9 0.016(6) 0.030(6) 0.050(6) -0.008(5) 0.011(5) -0.003(5) C10 0.006(7) 0.024(6) 0.058(8) -0.013(6) 0.005(6) 0.001(5) O3 0.021(4) 0.030(4) 0.071(5) 0.000(3) 0.003(4) 0.005(3) N4 0.020(6) 0.033(5) 0.054(6) 0.014(5) 0.007(4) 0.008(4) C11 0.057(7) 0.032(6) 0.059(7) 0.004(6) 0.008(6) 0.007(6) C12 0.034(8) 0.017(6) 0.049(7) 0.004(6) 0.008(6) 0.001(5) O4 0.059(5) 0.032(4) 0.056(5) 0.006(4) 0.014(4) -0.007(4) C13 0.016(6) 0.039(6) 0.044(6) 0.002(6) 0.013(5) -0.004(5) C14 0.058(7) 0.053(7) 0.054(8) -0.002(6) 0.027(7) 0.019(6) C15 0.057(8) 0.051(7) 0.037(8) -0.004(6) 0.018(6) 0.002(6) C16 0.091(10) 0.059(8) 0.042(9) -0.001(6) 0.010(7) 0.028(7) C17 0.113(11) 0.056(8) 0.057(9) -0.002(8) 0.007(9) -0.002(7) C18 0.114(12) 0.055(9) 0.064(11) -0.007(8) 0.005(9) -0.001(8) C19 0.145(13) 0.061(9) 0.043(10) -0.023(7) 0.037(8) 0.009(9) C20 0.105(10) 0.082(10) 0.054(9) -0.007(8) 0.032(8) 0.012(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 N1 1.443(11) . ? C1 N2 1.473(10) . ? C1 C13 1.569(12) . ? N1 C14 1.433(11) . ? N1 C2 1.454(12) . ? C2 C3 1.533(13) . ? C3 N2 1.491(11) . ? N2 C4 1.453(10) . ? C4 C5 1.506(12) . ? C4 C8 1.525(11) . ? C4 C9 1.571(12) . ? C5 O1 1.216(10) . ? C5 N3 1.372(11) . ? N3 C7 1.389(11) . ? N3 C6 1.436(10) . ? C7 O2 1.217(10) . ? C7 C8 1.468(12) . ? O2 C7 3.094(10) 3_676 ? C9 C10 1.484(12) . ? C9 C13 1.507(11) . ? C10 O3 1.217(9) . ? C10 N4 1.383(11) . ? N4 C12 1.389(11) . ? N4 C11 1.439(11) . ? C12 O4 1.206(10) . ? C12 C13 1.491(12) . ? C14 C15 1.506(13) . ? C15 C20 1.368(14) . ? C15 C16 1.392(14) . ? C16 C17 1.357(14) . ? C17 C18 1.365(15) . ? C18 C19 1.364(16) . ? C19 C20 1.395(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 N1 C1 N2 107.0(7) . . ? N1 C1 C13 113.5(7) . . ? N2 C1 C13 107.0(6) . . ? C14 N1 C1 116.0(8) . . ? C14 N1 C2 113.6(8) . . ? C1 N1 C2 105.7(7) . . ? N1 C2 C3 102.2(7) . . ? N2 C3 C2 100.2(7) . . ? C4 N2 C1 109.5(7) . . ? C4 N2 C3 118.4(7) . . ? C1 N2 C3 106.4(7) . . ? N2 C4 C5 106.0(7) . . ? N2 C4 C8 115.8(7) . . ? C5 C4 C8 103.7(7) . . ? N2 C4 C9 104.7(7) . . ? C5 C4 C9 108.0(7) . . ? C8 C4 C9 117.9(7) . . ? O1 C5 N3 123.8(9) . . ? O1 C5 C4 126.7(9) . . ? N3 C5 C4 109.5(8) . . ? C5 N3 C7 111.1(8) . . ? C5 N3 C6 124.2(8) . . ? C7 N3 C6 124.6(8) . . ? O2 C7 N3 121.7(9) . . ? O2 C7 C8 128.5(9) . . ? N3 C7 C8 109.7(9) . . ? C7 O2 C7 92.9(6) . 3_676 ? C7 C8 C4 105.6(7) . . ? C10 C9 C13 104.6(7) . . ? C10 C9 C4 115.4(7) . . ? C13 C9 C4 105.2(7) . . ? O3 C10 N4 121.6(8) . . ? O3 C10 C9 129.5(9) . . ? N4 C10 C9 108.9(8) . . ? C10 N4 C12 111.4(8) . . ? C10 N4 C11 124.7(8) . . ? C12 N4 C11 123.7(8) . . ? O4 C12 N4 123.0(9) . . ? O4 C12 C13 129.1(9) . . ? N4 C12 C13 107.9(8) . . ? C12 C13 C9 104.7(7) . . ? C12 C13 C1 110.1(7) . . ? C9 C13 C1 105.1(7) . . ? N1 C14 C15 113.2(8) . . ? C20 C15 C16 117.5(10) . . ? C20 C15 C14 122.1(11) . . ? C16 C15 C14 120.3(9) . . ? C17 C16 C15 121.5(11) . . ? C16 C17 C18 121.0(12) . . ? C19 C18 C17 118.6(12) . . ? C18 C19 C20 120.8(11) . . ? C15 C20 C19 120.4(12) . . ? 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 N2 C1 N1 C14 147.2(7) . . . . ? C13 C1 N1 C14 -95.0(9) . . . . ? N2 C1 N1 C2 20.4(8) . . . . ? C13 C1 N1 C2 138.1(7) . . . . ? C14 N1 C2 C3 -167.3(8) . . . . ? C1 N1 C2 C3 -39.0(8) . . . . ? N1 C2 C3 N2 41.8(8) . . . . ? N1 C1 N2 C4 136.2(7) . . . . ? C13 C1 N2 C4 14.2(9) . . . . ? N1 C1 N2 C3 7.2(8) . . . . ? C13 C1 N2 C3 -114.8(7) . . . . ? C2 C3 N2 C4 -153.5(7) . . . . ? C2 C3 N2 C1 -29.8(8) . . . . ? C1 N2 C4 C5 86.9(8) . . . . ? C3 N2 C4 C5 -150.9(7) . . . . ? C1 N2 C4 C8 -158.6(7) . . . . ? C3 N2 C4 C8 -36.5(10) . . . . ? C1 N2 C4 C9 -27.1(8) . . . . ? C3 N2 C4 C9 95.0(8) . . . . ? N2 C4 C5 O1 -61.4(10) . . . . ? C8 C4 C5 O1 176.1(8) . . . . ? C9 C4 C5 O1 50.3(11) . . . . ? N2 C4 C5 N3 117.5(7) . . . . ? C8 C4 C5 N3 -5.0(8) . . . . ? C9 C4 C5 N3 -130.8(7) . . . . ? O1 C5 N3 C7 -174.4(7) . . . . ? C4 C5 N3 C7 6.7(9) . . . . ? O1 C5 N3 C6 1.7(12) . . . . ? C4 C5 N3 C6 -177.2(7) . . . . ? C5 N3 C7 O2 176.9(8) . . . . ? C6 N3 C7 O2 0.9(12) . . . . ? C5 N3 C7 C8 -5.6(9) . . . . ? C6 N3 C7 C8 178.3(7) . . . . ? N3 C7 O2 C7 104.1(7) . . . 3_676 ? C8 C7 O2 C7 -72.7(8) . . . 3_676 ? O2 C7 C8 C4 179.4(8) . . . . ? N3 C7 C8 C4 2.2(9) . . . . ? N2 C4 C8 C7 -114.1(8) . . . . ? C5 C4 C8 C7 1.6(8) . . . . ? C9 C4 C8 C7 120.8(8) . . . . ? N2 C4 C9 C10 -85.0(8) . . . . ? C5 C4 C9 C10 162.3(8) . . . . ? C8 C4 C9 C10 45.3(11) . . . . ? N2 C4 C9 C13 29.7(9) . . . . ? C5 C4 C9 C13 -82.9(9) . . . . ? C8 C4 C9 C13 160.1(7) . . . . ? C13 C9 C10 O3 -172.5(8) . . . . ? C4 C9 C10 O3 -57.4(12) . . . . ? C13 C9 C10 N4 9.7(9) . . . . ? C4 C9 C10 N4 124.8(8) . . . . ? O3 C10 N4 C12 -178.3(7) . . . . ? C9 C10 N4 C12 -0.2(9) . . . . ? O3 C10 N4 C11 -2.9(12) . . . . ? C9 C10 N4 C11 175.1(8) . . . . ? C10 N4 C12 O4 170.7(8) . . . . ? C11 N4 C12 O4 -4.7(13) . . . . ? C10 N4 C12 C13 -9.6(9) . . . . ? C11 N4 C12 C13 174.9(7) . . . . ? O4 C12 C13 C9 -165.2(9) . . . . ? N4 C12 C13 C9 15.2(9) . . . . ? O4 C12 C13 C1 82.3(11) . . . . ? N4 C12 C13 C1 -97.3(8) . . . . ? C10 C9 C13 C12 -14.8(8) . . . . ? C4 C9 C13 C12 -136.8(7) . . . . ? C10 C9 C13 C1 101.2(7) . . . . ? C4 C9 C13 C1 -20.8(9) . . . . ? N1 C1 C13 C12 -0.4(10) . . . . ? N2 C1 C13 C12 117.4(8) . . . . ? N1 C1 C13 C9 -112.6(8) . . . . ? N2 C1 C13 C9 5.2(9) . . . . ? C1 N1 C14 C15 168.1(8) . . . . ? C2 N1 C14 C15 -69.1(10) . . . . ? N1 C14 C15 C20 146.4(10) . . . . ? N1 C14 C15 C16 -34.2(13) . . . . ? C20 C15 C16 C17 -0.4(17) . . . . ? C14 C15 C16 C17 -179.8(11) . . . . ? C15 C16 C17 C18 3.0(18) . . . . ? C16 C17 C18 C19 -2.7(18) . . . . ? C17 C18 C19 C20 0.0(19) . . . . ? C16 C15 C20 C19 -2.3(17) . . . . ? C14 C15 C20 C19 177.1(11) . . . . ? C18 C19 C20 C15 2.5(19) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.273 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.066 # Attachment '- Fig2.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 823960' #TrackingRef '- Fig2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H28 N2 O8' _chemical_formula_sum 'C22 H28 N2 O8' _chemical_formula_weight 448.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4904(10) _cell_length_b 12.842(2) _cell_length_c 13.370(2) _cell_angle_alpha 68.762(6) _cell_angle_beta 75.646(6) _cell_angle_gamma 80.916(8) _cell_volume 1158.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 19113 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 28.70 _exptl_crystal_description block _exptl_crystal_colour colourless _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 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9902 _exptl_absorpt_correction_T_max 0.9951 _exptl_absorpt_process_details ; SORTAV (R. H. Blessing, Acta Cryst. A51 (1995) 33-37; R. H. Blessing, J. Appl. Cryst. 30 (1997) 421-426). ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on a \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_reflns_number 4693 _diffrn_reflns_av_R_equivalents 0.0543 _diffrn_reflns_av_sigmaI/netI 0.1056 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3061 _reflns_number_gt 1524 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _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^)+(0.0697P)^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 SHELXL _refine_ls_extinction_coef 0.018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3061 _refine_ls_number_parameters 290 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1450 _refine_ls_R_factor_gt 0.0634 _refine_ls_wR_factor_ref 0.1648 _refine_ls_wR_factor_gt 0.1403 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.2508(4) 0.9215(2) 0.35988(18) 0.0668(8) Uani 1 1 d . . . O2 O -0.1452(4) 0.8335(3) 0.2390(2) 0.0875(10) Uani 1 1 d . . . O3 O 0.3783(4) 0.7454(2) 0.18895(19) 0.0727(9) Uani 1 1 d . . . O4 O 0.2644(4) 0.8927(3) 0.2408(2) 0.0888(10) Uani 1 1 d . . . O5 O -0.1771(4) 0.5568(2) 0.38952(19) 0.0643(8) Uani 1 1 d . . . O6 O -0.4352(5) 0.6577(3) 0.4370(2) 0.0905(11) Uani 1 1 d . . . O7 O -0.4581(4) 0.6705(3) 0.7498(2) 0.1083(13) Uani 1 1 d . . . O8 O -0.2259(6) 0.5445(3) 0.7204(2) 0.1015(12) Uani 1 1 d . . . N1 N -0.0555(4) 0.7855(2) 0.6652(2) 0.0575(9) Uani 1 1 d . . . N2 N 0.0116(4) 0.8218(2) 0.4756(2) 0.0508(8) Uani 1 1 d . . . C1 C -0.1428(5) 0.8136(3) 0.5701(2) 0.0556(11) Uani 1 1 d . . . H1 H -0.2171 0.8873 0.5593 0.067 Uiso 1 1 calc R . . C2 C -0.2661(5) 0.7211(3) 0.5754(2) 0.0564(11) Uani 1 1 d . . . H2 H -0.3843 0.7582 0.5525 0.068 Uiso 1 1 calc R . . C3 C -0.1528(5) 0.6691(3) 0.4911(2) 0.0489(10) Uani 1 1 d . . . H3 H -0.0718 0.6041 0.5282 0.059 Uiso 1 1 calc R . . C4 C -0.0281(5) 0.7642(3) 0.4078(2) 0.0483(10) Uani 1 1 d . . . C5 C 0.1848(6) 0.7864(4) 0.5183(3) 0.0679(12) Uani 1 1 d . . . H5A H 0.2905 0.8259 0.4648 0.081 Uiso 1 1 calc R . . H5B H 0.2146 0.7045 0.5376 0.081 Uiso 1 1 calc R . . C6 C 0.1341(6) 0.8212(4) 0.6195(3) 0.0708(12) Uani 1 1 d . . . H6A H 0.2171 0.7818 0.6711 0.085 Uiso 1 1 calc R . . H6B H 0.1367 0.9031 0.5999 0.085 Uiso 1 1 calc R . . C7 C -0.1438(5) 0.8439(3) 0.3235(3) 0.0537(11) Uani 1 1 d . . . C8 C -0.3753(6) 0.9947(4) 0.2914(3) 0.0827(13) Uani 1 1 d . . . H8A H -0.4457 1.0481 0.3261 0.124 Uiso 1 1 calc R . . H8B H -0.4607 0.9497 0.2826 0.124 Uiso 1 1 calc R . . H8C H -0.3034 1.0356 0.2193 0.124 Uiso 1 1 calc R . . C9 C 0.1447(5) 0.7125(3) 0.3459(2) 0.0545(11) Uani 1 1 d . . . H9A H 0.2212 0.6658 0.3992 0.065 Uiso 1 1 calc R . . H9B H 0.1038 0.6626 0.3157 0.065 Uiso 1 1 calc R . . C10 C 0.2626(5) 0.7959(4) 0.2543(3) 0.0578(11) Uani 1 1 d . . . C11 C 0.5047(6) 0.8155(4) 0.0973(3) 0.0957(17) Uani 1 1 d . . . H11A H 0.5814 0.7701 0.0551 0.144 Uiso 1 1 calc R . . H11B H 0.5840 0.8479 0.1250 0.144 Uiso 1 1 calc R . . H11C H 0.4341 0.8758 0.0501 0.144 Uiso 1 1 calc R . . C12 C -0.2741(7) 0.6285(3) 0.4380(3) 0.0559(11) Uani 1 1 d . . . C13 C -0.2711(6) 0.5283(4) 0.3204(3) 0.0767(13) Uani 1 1 d . . . H13A H -0.1904 0.4755 0.2884 0.115 Uiso 1 1 calc R . . H13B H -0.3006 0.5965 0.2616 0.115 Uiso 1 1 calc R . . H13C H -0.3855 0.4938 0.3649 0.115 Uiso 1 1 calc R . . C14 C -0.3092(7) 0.6337(5) 0.6884(3) 0.0724(13) Uani 1 1 d . . . C15 C -0.5130(9) 0.5918(6) 0.8616(3) 0.167(3) Uani 1 1 d . . . H15A H -0.6226 0.6243 0.9008 0.251 Uiso 1 1 calc R . . H15B H -0.4116 0.5773 0.9004 0.251 Uiso 1 1 calc R . . H15C H -0.5413 0.5214 0.8583 0.251 Uiso 1 1 calc R . . C16 C -0.1563(6) 0.8408(4) 0.7446(3) 0.0710(13) Uani 1 1 d . . . H16A H -0.2893 0.8283 0.7620 0.085 Uiso 1 1 calc R . . H16B H -0.1437 0.9225 0.7114 0.085 Uiso 1 1 calc R . . C17 C -0.0817(6) 0.7951(4) 0.8504(3) 0.0644(12) Uani 1 1 d . . . C18 C -0.0592(7) 0.6825(4) 0.9058(3) 0.0920(16) Uani 1 1 d . . . H18 H -0.0874 0.6309 0.8769 0.110 Uiso 1 1 calc R . . C19 C 0.0045(8) 0.6418(4) 1.0040(3) 0.0982(17) Uani 1 1 d . . . H19 H 0.0192 0.5633 1.0410 0.118 Uiso 1 1 calc R . . C20 C 0.0456(7) 0.7149(5) 1.0467(3) 0.0822(15) Uani 1 1 d . . . H20 H 0.0895 0.6877 1.1131 0.099 Uiso 1 1 calc R . . C21 C 0.0233(7) 0.8253(5) 0.9938(3) 0.0850(15) Uani 1 1 d . . . H21 H 0.0516 0.8760 1.0236 0.102 Uiso 1 1 calc R . . C22 C -0.0411(6) 0.8678(4) 0.8951(3) 0.0713(13) Uani 1 1 d . . . H22 H -0.0567 0.9465 0.8594 0.086 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0693(19) 0.0752(19) 0.0634(15) -0.0318(15) -0.0285(15) 0.0173(17) O2 0.105(3) 0.113(2) 0.0544(15) -0.0454(16) -0.0258(15) 0.021(2) O3 0.0661(19) 0.091(2) 0.0600(15) -0.0389(15) 0.0114(14) -0.0091(17) O4 0.097(2) 0.072(2) 0.0856(19) -0.0306(16) 0.0169(17) -0.0209(19) O5 0.0629(19) 0.0719(18) 0.0687(15) -0.0400(14) -0.0102(14) -0.0014(15) O6 0.052(2) 0.132(3) 0.118(2) -0.083(2) -0.0180(18) 0.002(2) O7 0.084(2) 0.168(3) 0.0544(16) -0.0360(19) 0.0127(17) -0.002(2) O8 0.128(3) 0.088(2) 0.0641(18) -0.0132(17) 0.0027(19) -0.007(2) N1 0.058(2) 0.074(2) 0.0474(16) -0.0326(15) -0.0164(16) 0.0128(18) N2 0.045(2) 0.063(2) 0.0486(15) -0.0261(14) -0.0098(15) 0.0028(16) C1 0.058(3) 0.066(3) 0.046(2) -0.0273(18) -0.0118(19) 0.008(2) C2 0.049(2) 0.079(3) 0.0403(18) -0.0257(18) -0.0057(17) 0.007(2) C3 0.043(2) 0.059(2) 0.0399(17) -0.0174(17) -0.0038(17) 0.006(2) C4 0.052(2) 0.054(2) 0.0409(18) -0.0228(17) -0.0047(18) -0.001(2) C5 0.056(3) 0.092(3) 0.061(2) -0.034(2) -0.009(2) -0.007(2) C6 0.072(3) 0.087(3) 0.061(2) -0.029(2) -0.021(2) -0.006(3) C7 0.049(3) 0.071(3) 0.046(2) -0.028(2) -0.0048(19) -0.006(2) C8 0.078(3) 0.086(3) 0.087(3) -0.029(2) -0.035(3) 0.016(3) C9 0.052(3) 0.062(2) 0.0466(19) -0.0233(18) -0.0010(18) 0.001(2) C10 0.052(3) 0.077(3) 0.052(2) -0.030(2) -0.010(2) -0.007(2) C11 0.081(3) 0.134(4) 0.059(2) -0.036(3) 0.028(2) -0.031(3) C12 0.053(3) 0.066(3) 0.047(2) -0.0186(19) -0.005(2) -0.012(2) C13 0.087(3) 0.084(3) 0.076(3) -0.042(2) -0.022(2) -0.010(3) C14 0.065(3) 0.099(4) 0.052(2) -0.031(3) 0.002(2) -0.010(3) C15 0.146(6) 0.262(8) 0.051(3) -0.024(4) 0.030(3) -0.042(6) C16 0.084(3) 0.082(3) 0.055(2) -0.038(2) -0.023(2) 0.020(2) C17 0.073(3) 0.078(3) 0.048(2) -0.034(2) -0.009(2) 0.002(3) C18 0.140(5) 0.076(4) 0.081(3) -0.043(3) -0.054(3) 0.022(3) C19 0.143(5) 0.088(4) 0.070(3) -0.027(3) -0.041(3) 0.004(4) C20 0.094(4) 0.106(4) 0.048(2) -0.029(3) -0.016(2) -0.003(3) C21 0.104(4) 0.108(4) 0.058(3) -0.039(3) -0.014(3) -0.028(3) C22 0.088(3) 0.076(3) 0.052(2) -0.028(2) -0.005(2) -0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C7 1.334(4) . ? O1 C8 1.454(5) . ? O2 C7 1.187(4) . ? O3 C10 1.339(4) . ? O3 C11 1.450(4) . ? O4 C10 1.191(4) . ? O5 C12 1.336(5) . ? O5 C13 1.460(4) . ? O6 C12 1.208(5) . ? O7 C14 1.343(5) . ? O7 C15 1.468(5) . ? O8 C14 1.199(5) . ? N1 C6 1.474(5) . ? N1 C1 1.475(4) . ? N1 C16 1.477(4) . ? N2 C4 1.465(4) . ? N2 C1 1.471(4) . ? N2 C5 1.486(5) . ? C1 C2 1.589(5) . ? C1 H1 1.0000 . ? C2 C14 1.513(5) . ? C2 C3 1.526(4) . ? C2 H2 1.0000 . ? C3 C12 1.530(5) . ? C3 C4 1.570(4) . ? C3 H3 1.0000 . ? C4 C9 1.548(4) . ? C4 C7 1.561(5) . ? C5 C6 1.518(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.496(5) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.531(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.371(6) . ? C17 C22 1.381(5) . ? C18 C19 1.400(6) . ? C18 H18 0.9500 . ? C19 C20 1.367(6) . ? C19 H19 0.9500 . ? C20 C21 1.340(6) . ? C20 H20 0.9500 . ? C21 C22 1.408(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 C7 O1 C8 116.9(3) . . ? C10 O3 C11 116.5(3) . . ? C12 O5 C13 115.0(3) . . ? C14 O7 C15 114.4(4) . . ? C6 N1 C1 105.8(3) . . ? C6 N1 C16 111.1(3) . . ? C1 N1 C16 112.6(3) . . ? C4 N2 C1 109.6(3) . . ? C4 N2 C5 118.4(3) . . ? C1 N2 C5 107.5(2) . . ? N2 C1 N1 105.2(3) . . ? N2 C1 C2 106.3(2) . . ? N1 C1 C2 115.0(3) . . ? N2 C1 H1 110.0 . . ? N1 C1 H1 110.0 . . ? C2 C1 H1 110.0 . . ? C14 C2 C3 111.4(3) . . ? C14 C2 C1 112.8(3) . . ? C3 C2 C1 104.6(2) . . ? C14 C2 H2 109.3 . . ? C3 C2 H2 109.3 . . ? C1 C2 H2 109.3 . . ? C2 C3 C12 112.5(3) . . ? C2 C3 C4 103.8(3) . . ? C12 C3 C4 113.7(3) . . ? C2 C3 H3 108.9 . . ? C12 C3 H3 108.9 . . ? C4 C3 H3 108.9 . . ? N2 C4 C9 114.7(3) . . ? N2 C4 C7 111.0(3) . . ? C9 C4 C7 109.0(2) . . ? N2 C4 C3 104.3(2) . . ? C9 C4 C3 109.8(3) . . ? C7 C4 C3 107.7(3) . . ? N2 C5 C6 101.4(3) . . ? N2 C5 H5A 111.5 . . ? C6 C5 H5A 111.5 . . ? N2 C5 H5B 111.5 . . ? C6 C5 H5B 111.5 . . ? H5A C5 H5B 109.3 . . ? N1 C6 C5 101.0(3) . . ? N1 C6 H6A 111.6 . . ? C5 C6 H6A 111.6 . . ? N1 C6 H6B 111.6 . . ? C5 C6 H6B 111.6 . . ? H6A C6 H6B 109.4 . . ? O2 C7 O1 123.2(4) . . ? O2 C7 C4 124.2(3) . . ? O1 C7 C4 112.4(3) . . ? O1 C8 H8A 109.5 . . ? O1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C4 114.8(3) . . ? C10 C9 H9A 108.6 . . ? C4 C9 H9A 108.6 . . ? C10 C9 H9B 108.6 . . ? C4 C9 H9B 108.6 . . ? H9A C9 H9B 107.5 . . ? O4 C10 O3 122.7(3) . . ? O4 C10 C9 127.1(3) . . ? O3 C10 C9 110.2(3) . . ? O3 C11 H11A 109.5 . . ? O3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O6 C12 O5 123.4(4) . . ? O6 C12 C3 125.7(4) . . ? O5 C12 C3 110.9(4) . . ? O5 C13 H13A 109.5 . . ? O5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O8 C14 O7 123.8(4) . . ? O8 C14 C2 126.5(4) . . ? O7 C14 C2 109.7(4) . . ? O7 C15 H15A 109.5 . . ? O7 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O7 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 C17 111.2(3) . . ? N1 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? N1 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C22 117.8(4) . . ? C18 C17 C16 121.9(4) . . ? C22 C17 C16 120.2(4) . . ? C17 C18 C19 121.4(4) . . ? C17 C18 H18 119.3 . . ? C19 C18 H18 119.3 . . ? C20 C19 C18 120.0(4) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 119.2(4) . . ? C21 C20 H20 120.4 . . ? C19 C20 H20 120.4 . . ? C20 C21 C22 121.6(4) . . ? C20 C21 H21 119.2 . . ? C22 C21 H21 119.2 . . ? C17 C22 C21 119.9(4) . . ? C17 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? _diffrn_measured_fraction_theta_max 0.711 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.726 _refine_diff_density_max 0.164 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.043 # Attachment '- Fig3.CIF' data_01src383 _database_code_depnum_ccdc_archive 'CCDC 823961' #TrackingRef '- Fig3.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H25 N3 O6' _chemical_formula_weight 415.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.331(2) _cell_length_b 13.023(3) _cell_length_c 15.005(3) _cell_angle_alpha 100.18(3) _cell_angle_beta 108.98(3) _cell_angle_gamma 90.44(3) _cell_volume 2055.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 21725 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 20.82 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 880 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.9901 _exptl_absorpt_correction_T_max 0.9980 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans to fill Ewald Sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7560 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.1097 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 20.76 _reflns_number_total 4048 _reflns_number_gt 2645 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin, Pearce 1993)' _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^)+(0.1927P)^2^+2.7954P] 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 0.020(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4048 _refine_ls_number_parameters 549 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1437 _refine_ls_R_factor_gt 0.1033 _refine_ls_wR_factor_ref 0.3028 _refine_ls_wR_factor_gt 0.2628 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.094 _refine_ls_shift/su_mean 0.026 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 -0.4815(9) 1.2466(7) -0.7205(6) 0.037(2) Uani 1 1 d . . . C2 C -0.6062(9) 1.2031(8) -0.7615(7) 0.052(3) Uani 1 1 d . . . H2 H -0.6402 1.1629 -0.7274 0.062 Uiso 1 1 calc R . . C3 C -0.6784(10) 1.2187(8) -0.8509(7) 0.055(3) Uani 1 1 d . . . H3 H -0.7620 1.1887 -0.8780 0.066 Uiso 1 1 calc R . . C4 C -0.6320(12) 1.2769(9) -0.9017(8) 0.067(3) Uani 1 1 d . . . H4 H -0.6835 1.2878 -0.9629 0.081 Uiso 1 1 calc R . . C5 C -0.5085(11) 1.3198(8) -0.8625(8) 0.064(3) Uani 1 1 d . . . H5 H -0.4746 1.3584 -0.8977 0.077 Uiso 1 1 calc R . . C6 C -0.4349(10) 1.3057(7) -0.7711(6) 0.044(3) Uani 1 1 d . . . H6 H -0.3520 1.3371 -0.7435 0.053 Uiso 1 1 calc R . . C7 C -0.4017(8) 1.2314(7) -0.6225(6) 0.037(2) Uani 1 1 d . . . H7A H -0.4312 1.1653 -0.6101 0.045 Uiso 1 1 calc R . . H7B H -0.3143 1.2247 -0.6215 0.045 Uiso 1 1 calc R . . C8 C -0.5275(8) 1.3258(6) -0.5356(6) 0.031(2) Uani 1 1 d . . . H8A H -0.5712 1.2559 -0.5483 0.038 Uiso 1 1 calc R . . H8B H -0.5796 1.3683 -0.5801 0.038 Uiso 1 1 calc R . . C9 C -0.4997(7) 1.3793(6) -0.4322(6) 0.032(2) Uani 1 1 d . . . H9A H -0.4766 1.4549 -0.4224 0.038 Uiso 1 1 calc R . . H9B H -0.5712 1.3695 -0.4095 0.038 Uiso 1 1 calc R . . C10 C -0.3187(7) 1.3066(6) -0.4516(6) 0.027(2) Uani 1 1 d . . . H10 H -0.2880 1.2347 -0.4557 0.032 Uiso 1 1 calc R . . C11 C -0.2031(8) 1.3894(6) -0.4089(6) 0.028(2) Uani 1 1 d . . . H11 H -0.1238 1.3527 -0.3927 0.034 Uiso 1 1 calc R . . C12 C -0.2017(8) 1.4603(7) -0.4783(6) 0.029(2) Uani 1 1 d . . . C13 C -0.1428(9) 1.4786(7) -0.6112(7) 0.040(2) Uani 1 1 d . . . H13A H -0.2262 1.4988 -0.6455 0.060 Uiso 1 1 calc R . . H13B H -0.1077 1.4391 -0.6574 0.060 Uiso 1 1 calc R . . H13C H -0.0881 1.5416 -0.5761 0.060 Uiso 1 1 calc R . . C14 C -0.2196(8) 1.4494(7) -0.3167(6) 0.030(2) Uani 1 1 d . . . H14 H -0.2667 1.5119 -0.3333 0.036 Uiso 1 1 calc R . . C15 C -0.0959(9) 1.4891(6) -0.2386(6) 0.030(2) Uani 1 1 d . . . C16 C -0.0024(12) 1.5852(11) -0.0843(9) 0.092(4) Uani 1 1 d U . . H16A H 0.0600 1.5331 -0.0725 0.137 Uiso 1 1 calc R . . H16B H -0.0223 1.6100 -0.0256 0.137 Uiso 1 1 calc R . . H16C H 0.0310 1.6443 -0.1032 0.137 Uiso 1 1 calc R . . C17 C -0.3061(7) 1.3759(6) -0.2909(6) 0.025(2) Uani 1 1 d . . . C18 C -0.3728(8) 1.4229(7) -0.2220(6) 0.034(2) Uani 1 1 d . . . H18A H -0.3443 1.4975 -0.1961 0.041 Uiso 1 1 calc R . . H18B H -0.4644 1.4177 -0.2553 0.041 Uiso 1 1 calc R . . C19 C -0.3412(8) 1.3617(7) -0.1426(6) 0.032(2) Uani 1 1 d . . . C20 C -0.2336(8) 1.2921(7) -0.2426(6) 0.029(2) Uani 1 1 d . . . C21 C -0.2048(9) 1.2149(7) -0.0974(7) 0.044(3) Uani 1 1 d . . . H21A H -0.2160 1.2366 -0.0349 0.066 Uiso 1 1 calc R . . H21B H -0.1154 1.2121 -0.0885 0.066 Uiso 1 1 calc R . . H21C H -0.2474 1.1456 -0.1277 0.066 Uiso 1 1 calc R . . C27 C 0.0147(8) 1.1529(7) 0.2691(6) 0.035(2) Uani 1 1 d . . . C28 C -0.1060(9) 1.1846(8) 0.2287(7) 0.051(3) Uani 1 1 d . . . H28 H -0.1345 1.2433 0.2613 0.061 Uiso 1 1 calc R . . C29 C -0.1834(10) 1.1296(9) 0.1411(7) 0.059(3) Uani 1 1 d . . . H29 H -0.2666 1.1493 0.1157 0.071 Uiso 1 1 calc R . . C30 C -0.1441(10) 1.0497(9) 0.0914(7) 0.052(3) Uani 1 1 d . . . H30 H -0.1981 1.0136 0.0309 0.062 Uiso 1 1 calc R . . C31 C -0.0246(11) 1.0204(8) 0.1292(7) 0.054(3) Uani 1 1 d . . . H31 H 0.0058 0.9649 0.0943 0.064 Uiso 1 1 calc R . . C32 C 0.0514(9) 1.0726(8) 0.2186(7) 0.045(3) Uani 1 1 d . . . H32 H 0.1330 1.0501 0.2449 0.053 Uiso 1 1 calc R . . C33 C 0.0994(8) 1.2117(7) 0.3656(6) 0.036(2) Uani 1 1 d . . . H33A H 0.1864 1.2157 0.3651 0.044 Uiso 1 1 calc R . . H33B H 0.0735 1.2840 0.3765 0.044 Uiso 1 1 calc R . . C34 C -0.0293(8) 1.1583(7) 0.4550(6) 0.030(2) Uani 1 1 d . . . H34A H -0.0835 1.0977 0.4112 0.036 Uiso 1 1 calc R . . H34B H -0.0703 1.2234 0.4416 0.036 Uiso 1 1 calc R . . C35 C -0.0030(7) 1.1495(6) 0.5569(6) 0.027(2) Uani 1 1 d . . . H35A H -0.0742 1.1702 0.5792 0.033 Uiso 1 1 calc R . . H35B H 0.0170 1.0778 0.5672 0.033 Uiso 1 1 calc R . . C36 C 0.1797(7) 1.2124(6) 0.5384(6) 0.027(2) Uani 1 1 d . . . H36 H 0.2101 1.2828 0.5333 0.033 Uiso 1 1 calc R . . C37 C 0.2961(7) 1.1486(6) 0.5849(6) 0.024(2) Uani 1 1 d . . . H37 H 0.3755 1.1932 0.6021 0.029 Uiso 1 1 calc R . . C38 C 0.3006(8) 1.0497(7) 0.5181(6) 0.025(2) Uani 1 1 d . . . C39 C 0.3554(9) 0.9738(7) 0.3846(6) 0.039(2) Uani 1 1 d . . . H39A H 0.4072 0.9245 0.4199 0.058 Uiso 1 1 calc R . . H39B H 0.3931 0.9938 0.3394 0.058 Uiso 1 1 calc R . . H39C H 0.2713 0.9407 0.3493 0.058 Uiso 1 1 calc R . . C40 C 0.2778(7) 1.1260(6) 0.6758(5) 0.026(2) Uani 1 1 d . . . H40 H 0.2315 1.0558 0.6592 0.032 Uiso 1 1 calc R . . C41 C 0.3980(9) 1.1229(6) 0.7574(6) 0.028(2) Uani 1 1 d . . . C42 C 0.4854(9) 1.1072(10) 0.9202(7) 0.065(3) Uani 1 1 d . . . H42A H 0.5327 1.0487 0.9031 0.097 Uiso 1 1 calc R . . H42B H 0.4580 1.0953 0.9734 0.097 Uiso 1 1 calc R . . H42C H 0.5388 1.1723 0.9398 0.097 Uiso 1 1 calc R . . C43 C 0.1884(8) 1.2095(6) 0.6990(6) 0.025(2) Uani 1 1 d . . . C44 C 0.1190(8) 1.1892(7) 0.7647(6) 0.036(2) Uani 1 1 d . . . H44A H 0.0277 1.1820 0.7301 0.043 Uiso 1 1 calc R . . H44B H 0.1441 1.1237 0.7885 0.043 Uiso 1 1 calc R . . C45 C 0.1511(8) 1.2799(7) 0.8466(6) 0.034(2) Uani 1 1 d . . . C46 C 0.2640(8) 1.3142(7) 0.7520(6) 0.032(2) Uani 1 1 d . . . C47 C 0.2926(9) 1.4464(7) 0.8995(6) 0.046(3) Uani 1 1 d . . . H47A H 0.3837 1.4487 0.9160 0.068 Uiso 1 1 calc R . . H47B H 0.2708 1.4517 0.9582 0.068 Uiso 1 1 calc R . . H47C H 0.2603 1.5050 0.8679 0.068 Uiso 1 1 calc R . . N1 N -0.4039(6) 1.3174(5) -0.5454(5) 0.0279(18) Uani 1 1 d . . . N2 N -0.3901(6) 1.3208(5) -0.3842(5) 0.0299(18) Uani 1 1 d . . . N3 N -0.2581(6) 1.2902(5) -0.1587(5) 0.0309(18) Uani 1 1 d . . . N4 N 0.0948(6) 1.1601(5) 0.4450(5) 0.0289(18) Uani 1 1 d . . . N5 N 0.1072(6) 1.2248(5) 0.6048(5) 0.0277(18) Uani 1 1 d . . . N6 N 0.2371(7) 1.3478(5) 0.8348(5) 0.0307(18) Uani 1 1 d . . . O1 O -0.2323(5) 1.5478(5) -0.4728(4) 0.0359(16) Uani 1 1 d . . . O2 O -0.1525(5) 1.4138(4) -0.5438(4) 0.0329(15) Uani 1 1 d . . . O3 O 0.0051(6) 1.4792(5) -0.2446(4) 0.0454(18) Uani 1 1 d . . . O4 O -0.1147(6) 1.5382(6) -0.1602(5) 0.074(3) Uani 1 1 d . . . O5 O -0.3785(6) 1.3711(5) -0.0747(5) 0.0492(18) Uani 1 1 d . . . O6 O -0.1636(5) 1.2348(5) -0.2715(4) 0.0365(16) Uani 1 1 d . . . O7 O 0.2644(5) 0.9628(4) 0.5224(4) 0.0320(15) Uani 1 1 d . . . O8 O 0.3475(5) 1.0657(4) 0.4513(4) 0.0321(15) Uani 1 1 d . . . O9 O 0.5006(6) 1.1300(5) 0.7526(4) 0.0413(17) Uani 1 1 d . . . O10 O 0.3770(6) 1.1148(6) 0.8379(4) 0.0515(19) Uani 1 1 d . . . O11 O 0.1114(6) 1.2964(5) 0.9131(5) 0.0504(19) Uani 1 1 d . . . O12 O 0.3364(6) 1.3608(4) 0.7251(4) 0.0365(16) 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 0.041(6) 0.037(6) 0.034(6) 0.004(5) 0.013(5) 0.005(5) C2 0.043(7) 0.061(7) 0.046(7) 0.012(5) 0.006(6) -0.007(5) C3 0.046(7) 0.066(8) 0.037(7) 0.007(6) -0.007(6) -0.008(5) C4 0.086(10) 0.063(8) 0.044(7) 0.016(6) 0.005(7) 0.013(7) C5 0.083(9) 0.039(7) 0.058(8) 0.003(6) 0.012(7) -0.004(6) C6 0.059(7) 0.037(6) 0.023(6) 0.003(5) -0.003(5) -0.001(5) C7 0.036(6) 0.041(6) 0.035(6) 0.011(5) 0.009(5) 0.013(5) C8 0.032(6) 0.021(5) 0.037(6) 0.009(4) 0.005(4) 0.001(4) C9 0.022(5) 0.027(5) 0.046(6) 0.018(5) 0.005(4) 0.003(4) C10 0.024(5) 0.023(5) 0.029(5) 0.004(4) 0.005(4) -0.005(4) C11 0.026(5) 0.022(5) 0.037(6) 0.012(4) 0.008(4) 0.008(4) C12 0.021(5) 0.020(6) 0.045(6) 0.009(5) 0.008(4) -0.001(4) C13 0.051(6) 0.032(6) 0.048(6) 0.016(5) 0.026(5) 0.006(5) C14 0.027(5) 0.032(5) 0.028(5) 0.011(4) 0.003(4) 0.006(4) C15 0.041(7) 0.021(5) 0.036(6) 0.007(4) 0.022(5) 0.003(4) C16 0.091(4) 0.092(4) 0.091(4) 0.0163(13) 0.0303(17) 0.0061(11) C17 0.025(5) 0.018(5) 0.035(6) 0.010(4) 0.014(4) -0.005(4) C18 0.030(5) 0.041(6) 0.032(5) 0.008(5) 0.013(4) 0.002(4) C19 0.033(6) 0.026(6) 0.033(6) -0.003(4) 0.009(5) -0.017(4) C20 0.031(5) 0.028(5) 0.030(6) 0.007(4) 0.011(5) 0.002(4) C21 0.039(6) 0.045(6) 0.050(6) 0.018(5) 0.011(5) -0.001(5) C27 0.036(6) 0.036(6) 0.033(6) 0.012(5) 0.009(5) 0.006(5) C28 0.047(7) 0.053(7) 0.046(7) 0.010(6) 0.007(6) 0.012(6) C29 0.058(7) 0.067(8) 0.030(6) 0.002(6) -0.011(6) 0.017(6) C30 0.053(8) 0.067(8) 0.026(6) 0.001(6) 0.005(5) 0.000(6) C31 0.069(8) 0.045(7) 0.048(7) 0.008(6) 0.023(6) 0.008(6) C32 0.049(6) 0.047(7) 0.030(6) 0.014(5) 0.001(5) 0.006(5) C33 0.037(6) 0.040(6) 0.036(6) 0.018(5) 0.011(5) -0.001(4) C34 0.029(6) 0.026(5) 0.032(6) 0.009(4) 0.004(4) 0.005(4) C35 0.020(5) 0.025(5) 0.037(6) 0.006(4) 0.010(4) 0.000(4) C36 0.028(5) 0.023(5) 0.032(6) 0.000(4) 0.014(5) 0.006(4) C37 0.022(5) 0.018(5) 0.034(5) 0.004(4) 0.012(4) -0.001(4) C38 0.031(5) 0.019(6) 0.027(5) 0.011(4) 0.007(4) 0.010(4) C39 0.045(6) 0.031(6) 0.040(6) 0.004(5) 0.014(5) 0.010(5) C40 0.028(5) 0.023(5) 0.025(5) 0.003(4) 0.006(4) 0.009(4) C41 0.028(6) 0.018(5) 0.044(6) 0.006(4) 0.018(5) -0.001(4) C42 0.048(7) 0.122(11) 0.030(6) 0.040(6) 0.008(5) 0.022(7) C43 0.032(5) 0.022(5) 0.020(5) 0.004(4) 0.007(4) 0.001(4) C44 0.036(6) 0.046(6) 0.026(5) 0.012(5) 0.009(4) 0.011(5) C45 0.030(6) 0.048(6) 0.021(6) 0.002(5) 0.005(5) 0.009(5) C46 0.031(6) 0.028(5) 0.032(6) 0.008(5) 0.003(5) 0.010(5) C47 0.046(6) 0.046(6) 0.035(6) -0.010(5) 0.009(5) 0.003(5) N1 0.023(4) 0.024(4) 0.032(5) 0.005(3) 0.005(4) 0.004(3) N2 0.030(4) 0.033(4) 0.028(4) 0.015(4) 0.008(4) 0.013(4) N3 0.029(4) 0.034(5) 0.029(5) 0.014(4) 0.006(4) 0.010(4) N4 0.019(4) 0.038(4) 0.026(4) 0.012(3) -0.001(3) 0.005(3) N5 0.028(4) 0.020(4) 0.035(5) 0.005(3) 0.011(4) 0.008(3) N6 0.035(5) 0.032(5) 0.025(5) 0.007(4) 0.009(4) 0.009(4) O1 0.043(4) 0.021(4) 0.051(4) 0.013(3) 0.020(3) 0.011(3) O2 0.039(4) 0.034(4) 0.031(4) 0.012(3) 0.014(3) 0.012(3) O3 0.025(4) 0.065(5) 0.043(4) 0.005(3) 0.010(3) -0.003(3) O4 0.029(4) 0.109(7) 0.062(5) -0.038(5) 0.012(4) -0.025(4) O5 0.057(5) 0.054(5) 0.040(4) 0.007(3) 0.021(4) -0.001(3) O6 0.029(4) 0.041(4) 0.037(4) 0.010(3) 0.006(3) 0.009(3) O7 0.040(4) 0.018(4) 0.042(4) 0.006(3) 0.018(3) 0.004(3) O8 0.032(4) 0.038(4) 0.029(4) 0.002(3) 0.016(3) 0.002(3) O9 0.032(4) 0.057(5) 0.037(4) 0.014(3) 0.012(3) 0.002(3) O10 0.035(4) 0.087(5) 0.042(4) 0.038(4) 0.012(3) 0.012(3) O11 0.051(4) 0.062(5) 0.037(4) 0.001(3) 0.018(4) 0.003(4) O12 0.041(4) 0.030(4) 0.040(4) 0.009(3) 0.015(3) -0.002(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 C6 1.382(13) . ? C1 C2 1.412(13) . ? C1 C7 1.503(12) . ? C2 C3 1.377(13) . ? C3 C4 1.375(15) . ? C4 C5 1.398(15) . ? C5 C6 1.399(13) . ? C7 N1 1.467(10) . ? C8 N1 1.458(10) . ? C8 C9 1.513(11) . ? C9 N2 1.506(10) . ? C10 N1 1.456(10) . ? C10 N2 1.476(10) . ? C10 C11 1.573(11) . ? C11 C12 1.513(12) . ? C11 C14 1.531(11) . ? C12 O1 1.190(9) . ? C12 O2 1.339(10) . ? C13 O2 1.457(10) . ? C14 C15 1.521(12) . ? C14 C17 1.546(11) . ? C15 O3 1.183(9) . ? C15 O4 1.317(10) . ? C16 O4 1.445(14) . ? C17 N2 1.466(10) . ? C17 C20 1.517(12) . ? C17 C18 1.519(11) . ? C18 C19 1.497(12) . ? C19 O5 1.212(10) . ? C19 N3 1.376(11) . ? C20 O6 1.222(10) . ? C20 N3 1.379(11) . ? C21 N3 1.462(11) . ? C27 C32 1.332(12) . ? C27 C28 1.402(13) . ? C27 C33 1.515(12) . ? C28 C29 1.385(14) . ? C29 C30 1.337(14) . ? C30 C31 1.373(14) . ? C31 C32 1.385(13) . ? C33 N4 1.482(10) . ? C34 N4 1.462(10) . ? C34 C35 1.485(11) . ? C35 N5 1.478(10) . ? C36 N4 1.459(10) . ? C36 N5 1.474(10) . ? C36 C37 1.595(11) . ? C37 C38 1.498(11) . ? C37 C40 1.522(11) . ? C38 O7 1.221(9) . ? C38 O8 1.323(10) . ? C39 O8 1.440(10) . ? C40 C41 1.513(12) . ? C40 C43 1.562(11) . ? C41 O9 1.192(9) . ? C41 O10 1.327(10) . ? C42 O10 1.450(11) . ? C43 N5 1.464(10) . ? C43 C44 1.502(11) . ? C43 C46 1.543(12) . ? C44 C45 1.492(12) . ? C45 O11 1.209(10) . ? C45 N6 1.385(12) . ? C46 O12 1.224(10) . ? C46 N6 1.372(11) . ? C47 N6 1.462(11) . ? 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 118.8(9) . . ? C6 C1 C7 120.4(8) . . ? C2 C1 C7 120.8(8) . . ? C3 C2 C1 120.0(9) . . ? C2 C3 C4 121.3(10) . . ? C3 C4 C5 119.4(10) . . ? C4 C5 C6 119.7(11) . . ? C1 C6 C5 120.7(9) . . ? N1 C7 C1 113.2(7) . . ? N1 C8 C9 103.5(6) . . ? N2 C9 C8 99.9(6) . . ? N1 C10 N2 107.5(6) . . ? N1 C10 C11 114.7(6) . . ? N2 C10 C11 107.1(6) . . ? C12 C11 C14 112.2(7) . . ? C12 C11 C10 111.5(7) . . ? C14 C11 C10 103.8(6) . . ? O1 C12 O2 124.0(8) . . ? O1 C12 C11 125.3(8) . . ? O2 C12 C11 110.6(7) . . ? C15 C14 C11 113.0(7) . . ? C15 C14 C17 116.3(7) . . ? C11 C14 C17 105.2(7) . . ? O3 C15 O4 122.8(9) . . ? O3 C15 C14 126.4(8) . . ? O4 C15 C14 110.8(8) . . ? N2 C17 C20 105.5(6) . . ? N2 C17 C18 114.1(7) . . ? C20 C17 C18 103.2(6) . . ? N2 C17 C14 104.1(6) . . ? C20 C17 C14 111.1(6) . . ? C18 C17 C14 118.3(7) . . ? C19 C18 C17 106.8(7) . . ? O5 C19 N3 124.0(8) . . ? O5 C19 C18 128.3(9) . . ? N3 C19 C18 107.7(8) . . ? O6 C20 N3 124.3(8) . . ? O6 C20 C17 126.6(8) . . ? N3 C20 C17 109.1(7) . . ? C32 C27 C28 117.7(9) . . ? C32 C27 C33 122.4(9) . . ? C28 C27 C33 119.9(9) . . ? C29 C28 C27 119.5(10) . . ? C30 C29 C28 121.6(10) . . ? C29 C30 C31 119.0(10) . . ? C30 C31 C32 119.5(10) . . ? C27 C32 C31 122.6(10) . . ? N4 C33 C27 111.7(7) . . ? N4 C34 C35 103.5(6) . . ? N5 C35 C34 100.9(6) . . ? N4 C36 N5 106.8(6) . . ? N4 C36 C37 115.0(6) . . ? N5 C36 C37 105.9(6) . . ? C38 C37 C40 111.4(7) . . ? C38 C37 C36 111.6(6) . . ? C40 C37 C36 104.9(6) . . ? O7 C38 O8 122.2(7) . . ? O7 C38 C37 124.9(8) . . ? O8 C38 C37 112.8(7) . . ? C41 C40 C37 114.5(7) . . ? C41 C40 C43 114.8(6) . . ? C37 C40 C43 104.5(6) . . ? O9 C41 O10 122.8(8) . . ? O9 C41 C40 125.2(8) . . ? O10 C41 C40 112.0(8) . . ? N5 C43 C44 113.9(7) . . ? N5 C43 C46 107.7(6) . . ? C44 C43 C46 102.8(7) . . ? N5 C43 C40 104.3(6) . . ? C44 C43 C40 117.9(7) . . ? C46 C43 C40 110.0(7) . . ? C45 C44 C43 107.4(7) . . ? O11 C45 N6 123.1(9) . . ? O11 C45 C44 128.6(9) . . ? N6 C45 C44 108.2(8) . . ? O12 C46 N6 124.8(8) . . ? O12 C46 C43 126.0(8) . . ? N6 C46 C43 109.2(8) . . ? C10 N1 C8 106.2(6) . . ? C10 N1 C7 113.1(6) . . ? C8 N1 C7 112.4(6) . . ? C17 N2 C10 107.8(6) . . ? C17 N2 C9 115.5(6) . . ? C10 N2 C9 103.8(6) . . ? C19 N3 C20 113.1(7) . . ? C19 N3 C21 124.8(7) . . ? C20 N3 C21 122.1(7) . . ? C36 N4 C34 105.4(6) . . ? C36 N4 C33 112.9(7) . . ? C34 N4 C33 112.6(6) . . ? C43 N5 C36 108.7(6) . . ? C43 N5 C35 116.2(6) . . ? C36 N5 C35 104.7(6) . . ? C46 N6 C45 112.3(8) . . ? C46 N6 C47 122.0(8) . . ? C45 N6 C47 125.6(7) . . ? C12 O2 C13 114.1(6) . . ? C15 O4 C16 114.6(8) . . ? C38 O8 C39 115.9(6) . . ? C41 O10 C42 116.8(7) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 20.76 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.712 _refine_diff_density_min -0.395 _refine_diff_density_rms 0.114