# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Hosahudya Gopi' _publ_contact_author_email hn.gopi@iiserpune.ac.in _publ_section_title ; A Facile Transformation of Amino acids to Functionalized Coumarins ; loop_ _publ_author_name H.Gopi A.Bandyopadhyay # Attachment 'ANUACUM.cif' data_anuacum _database_code_depnum_ccdc_archive 'CCDC 819624' #TrackingRef 'ANUACUM.cif' _audit_creation_method SHELXL-97 _chemical_name_common Boc-Ala-CuM _chemical_formula_moiety 'C17 H21 N O5' _chemical_formula_sum 'C17 H21 N O5' _chemical_compound_source Synthesis _exptl_crystal_recrystallization_method MeOH/H2O _chemical_melting_point 101.325 _exptl_crystal_description 'Rod shaped' _exptl_crystal_colour Colorless _diffrn_ambient_temperature 200(2) _diffrn_ambient_pressure 101.325 _chemical_formula_weight 319.35 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 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration syn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.122(3) _cell_length_b 10.084(6) _cell_length_c 16.501(10) _cell_angle_alpha 90.00 _cell_angle_beta 96.062(13) _cell_angle_gamma 90.00 _cell_volume 847.5(8) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 822 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 18.77 _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.251 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Graphite Monochromator' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4478 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 20.81 _reflns_number_total 1623 _reflns_number_gt 1288 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0843P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(2) _refine_ls_number_reflns 1623 _refine_ls_number_parameters 213 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1331 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.4422(4) 0.7197(4) 0.48559(17) 0.0652(10) Uani 1 1 d . . . O2 O 0.7816(5) 0.7054(4) 0.38666(18) 0.0751(11) Uani 1 1 d . . . O3 O -0.0145(12) 1.0910(6) 0.2285(3) 0.146(2) Uani 1 1 d . . . O4 O 0.3007(8) 1.0319(4) 0.1345(2) 0.0886(12) Uani 1 1 d . . . O5 O 0.9567(7) 0.9325(5) -0.0725(2) 0.0895(13) Uani 1 1 d . . . N1 N 0.3609(6) 0.6941(4) 0.3589(2) 0.0638(13) Uani 1 1 d . . . H1 H 0.2021 0.6944 0.3715 0.077 Uiso 1 1 calc R . . C1 C 0.6125(7) 0.7309(7) 0.5541(3) 0.0677(15) Uani 1 1 d . . . C2 C 0.7680(11) 0.6042(6) 0.5587(4) 0.097(2) Uani 1 1 d . . . H2A H 0.6503 0.5300 0.5576 0.146 Uiso 1 1 calc R . . H2B H 0.8837 0.6026 0.6085 0.146 Uiso 1 1 calc R . . H2C H 0.8694 0.5992 0.5131 0.146 Uiso 1 1 calc R . . C3 C 0.4120(9) 0.7463(12) 0.6277(3) 0.138(4) Uani 1 1 d . . . H3A H 0.3005 0.8221 0.6166 0.206 Uiso 1 1 calc R . . H3B H 0.5147 0.7576 0.6793 0.206 Uiso 1 1 calc R . . H3C H 0.3060 0.6680 0.6291 0.206 Uiso 1 1 calc R . . C4 C 0.7840(10) 0.8493(6) 0.5433(4) 0.0851(18) Uani 1 1 d . . . H4A H 0.8957 0.8311 0.5014 0.128 Uiso 1 1 calc R . . H4B H 0.8900 0.8675 0.5936 0.128 Uiso 1 1 calc R . . H4C H 0.6759 0.9248 0.5280 0.128 Uiso 1 1 calc R . . C5 C 0.5459(8) 0.7059(5) 0.4095(3) 0.0534(12) Uani 1 1 d . . . C6 C 0.4239(8) 0.6785(5) 0.2718(3) 0.0599(14) Uani 1 1 d . . . H6 H 0.6096 0.6541 0.2732 0.072 Uiso 1 1 calc R . . C7 C 0.2653(11) 0.5625(6) 0.2410(4) 0.0824(17) Uani 1 1 d . . . H7A H 0.0823 0.5815 0.2428 0.124 Uiso 1 1 calc R . . H7B H 0.3133 0.4866 0.2745 0.124 Uiso 1 1 calc R . . H7C H 0.2975 0.5442 0.1859 0.124 Uiso 1 1 calc R . . C8 C 0.3843(8) 0.8039(5) 0.2253(3) 0.0599(14) Uani 1 1 d . . . C9 C 0.1996(11) 0.8928(6) 0.2523(3) 0.0769(17) Uani 1 1 d . . . H9 H 0.1121 0.8741 0.2975 0.092 Uiso 1 1 calc R . . C10 C 0.1528(13) 1.0119(7) 0.2074(4) 0.093(2) Uani 1 1 d . . . C11 C 0.4914(9) 0.9435(6) 0.1050(3) 0.0667(15) Uani 1 1 d . . . C12 C 0.6319(10) 0.9751(6) 0.0331(3) 0.0743(16) Uani 1 1 d . . . H12 H 0.5934 1.0561 0.0076 0.089 Uiso 1 1 calc R . . C13 C 0.8243(9) 0.8913(6) -0.0013(3) 0.0701(16) Uani 1 1 d . . . C14 C 0.8717(9) 0.7732(6) 0.0374(3) 0.0713(16) Uani 1 1 d . . . H14 H 0.9889 0.7125 0.0190 0.086 Uiso 1 1 calc R . . C15 C 0.7294(8) 0.7431(6) 0.1110(3) 0.0676(14) Uani 1 1 d . . . H15 H 0.7693 0.6621 0.1363 0.081 Uiso 1 1 calc R . . C16 C 0.5353(8) 0.8256(5) 0.1479(3) 0.0569(13) Uani 1 1 d . . . C17 C 1.1485(12) 0.8443(7) -0.1126(4) 0.099(2) Uani 1 1 d . . . H17A H 1.3022 0.8295 -0.0752 0.148 Uiso 1 1 calc R . . H17B H 1.1977 0.8871 -0.1607 0.148 Uiso 1 1 calc R . . H17C H 1.0662 0.7609 -0.1272 0.148 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 0.0362(14) 0.105(3) 0.050(2) -0.003(2) -0.0146(14) -0.0028(18) O2 0.0417(17) 0.115(3) 0.065(2) -0.002(2) -0.0114(13) 0.0020(19) O3 0.203(5) 0.131(5) 0.106(4) 0.018(3) 0.025(4) 0.103(4) O4 0.113(3) 0.079(3) 0.072(3) 0.010(2) -0.003(2) 0.036(2) O5 0.109(3) 0.092(3) 0.067(3) 0.012(3) 0.006(2) -0.008(2) N1 0.0337(19) 0.097(4) 0.056(3) 0.003(3) -0.0146(18) 0.002(2) C1 0.045(2) 0.102(5) 0.051(3) 0.003(3) -0.018(2) -0.011(3) C2 0.108(4) 0.061(4) 0.107(5) 0.011(4) -0.063(4) -0.011(3) C3 0.073(3) 0.282(12) 0.053(4) -0.022(6) -0.013(3) -0.020(6) C4 0.072(3) 0.071(4) 0.105(5) -0.008(4) -0.024(3) 0.005(3) C5 0.041(3) 0.059(3) 0.058(3) 0.009(3) -0.003(3) 0.006(2) C6 0.048(3) 0.084(4) 0.045(3) -0.003(3) -0.006(2) 0.006(2) C7 0.094(4) 0.074(4) 0.076(4) -0.005(3) -0.010(3) 0.006(3) C8 0.058(3) 0.066(4) 0.051(3) -0.003(3) -0.016(2) 0.012(3) C9 0.090(4) 0.081(5) 0.058(4) 0.005(3) -0.004(3) 0.014(3) C10 0.123(5) 0.070(5) 0.083(5) 0.008(4) -0.002(4) 0.046(4) C11 0.080(3) 0.067(4) 0.050(4) -0.001(3) -0.008(3) 0.010(3) C12 0.094(3) 0.059(4) 0.065(4) 0.004(3) -0.015(3) 0.003(3) C13 0.076(3) 0.076(5) 0.055(4) 0.003(3) -0.008(3) -0.009(3) C14 0.075(3) 0.071(5) 0.065(4) 0.005(3) -0.006(3) 0.007(3) C15 0.066(3) 0.073(4) 0.060(3) 0.008(3) -0.012(2) 0.003(3) C16 0.059(3) 0.051(4) 0.057(3) -0.004(3) -0.013(2) 0.005(2) C17 0.114(4) 0.100(5) 0.082(4) -0.003(4) 0.011(3) -0.021(4) _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 C1 1.358(5) . ? O1 C5 1.420(5) . ? O2 C5 1.302(5) . ? O3 C10 1.247(7) . ? O4 C11 1.444(6) . ? O4 C10 1.500(7) . ? O5 C13 1.477(6) . ? O5 C17 1.527(7) . ? N1 C5 1.201(5) . ? N1 C6 1.515(6) . ? C1 C2 1.503(8) . ? C1 C4 1.504(8) . ? C1 C3 1.678(7) . ? C6 C8 1.482(7) . ? C6 C7 1.483(7) . ? C8 C9 1.409(7) . ? C8 C16 1.577(7) . ? C9 C10 1.418(8) . ? C11 C16 1.390(8) . ? C11 C12 1.486(7) . ? C12 C13 1.458(7) . ? C13 C14 1.361(7) . ? C14 C15 1.512(7) . ? C15 C16 1.477(7) . ? 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 C1 O1 C5 118.5(3) . . ? C11 O4 C10 127.1(5) . . ? C13 O5 C17 123.5(5) . . ? C5 N1 C6 116.0(4) . . ? O1 C1 C2 105.2(5) . . ? O1 C1 C4 107.4(4) . . ? C2 C1 C4 111.6(4) . . ? O1 C1 C3 102.8(3) . . ? C2 C1 C3 113.8(6) . . ? C4 C1 C3 115.0(5) . . ? N1 C5 O2 119.1(4) . . ? N1 C5 O1 106.4(3) . . ? O2 C5 O1 134.5(4) . . ? C8 C6 C7 117.1(4) . . ? C8 C6 N1 111.8(4) . . ? C7 C6 N1 104.1(4) . . ? C9 C8 C6 116.1(5) . . ? C9 C8 C16 124.8(5) . . ? C6 C8 C16 119.1(4) . . ? C8 C9 C10 117.1(5) . . ? O3 C10 C9 118.6(6) . . ? O3 C10 O4 123.9(6) . . ? C9 C10 O4 117.4(5) . . ? C16 C11 O4 115.8(5) . . ? C16 C11 C12 121.6(5) . . ? O4 C11 C12 122.6(5) . . ? C13 C12 C11 126.2(5) . . ? C14 C13 C12 114.8(5) . . ? C14 C13 O5 123.0(5) . . ? C12 C13 O5 122.2(5) . . ? C13 C14 C15 118.4(5) . . ? C16 C15 C14 128.4(5) . . ? C11 C16 C15 110.6(5) . . ? C11 C16 C8 117.7(4) . . ? C15 C16 C8 131.7(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 20.81 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.126 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.035 # Attachment 'ANU-PCUM.cif' data_anu_pcum _database_code_depnum_ccdc_archive 'CCDC 819625' #TrackingRef 'ANU-PCUM.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H23 N O5' _chemical_formula_weight 345.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 16.779(3) _cell_length_b 10.0638(17) _cell_length_c 11.0022(19) _cell_angle_alpha 90.00 _cell_angle_beta 103.905(4) _cell_angle_gamma 90.00 _cell_volume 1803.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8001 _diffrn_reflns_av_R_equivalents 0.0216 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3198 _reflns_number_gt 2882 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(8) _refine_ls_number_reflns 3198 _refine_ls_number_parameters 230 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0936 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.82655(7) 0.58286(13) 0.20613(10) 0.0311(3) Uani 1 1 d . . . O2 O 0.79712(7) 0.72979(12) 0.34812(11) 0.0354(3) Uani 1 1 d . . . O3 O 0.89390(7) 0.38171(14) 0.71649(12) 0.0369(3) Uani 1 1 d . . . O4 O 0.79649(7) 0.49591(12) 0.77345(10) 0.0294(3) Uani 1 1 d . . . O5 O 0.57994(7) 0.71334(14) 0.90814(10) 0.0385(3) Uani 1 1 d . . . N1 N 0.72711(8) 0.53681(13) 0.29977(12) 0.0252(3) Uani 1 1 d . . . C1 C 0.90621(10) 0.64337(19) 0.20391(16) 0.0324(4) Uani 1 1 d . . . C2 C 0.93606(12) 0.5558(3) 0.11207(19) 0.0475(5) Uani 1 1 d . . . H2A H 0.8971 0.5582 0.0324 0.071 Uiso 1 1 calc R . . H2B H 0.9418 0.4661 0.1428 0.071 Uiso 1 1 calc R . . H2C H 0.9883 0.5875 0.1029 0.071 Uiso 1 1 calc R . . C3 C 0.89441(15) 0.7859(2) 0.1599(3) 0.0569(6) Uani 1 1 d . . . H3A H 0.8781 0.8387 0.2224 0.085 Uiso 1 1 calc R . . H3B H 0.8526 0.7899 0.0831 0.085 Uiso 1 1 calc R . . H3C H 0.9450 0.8196 0.1462 0.085 Uiso 1 1 calc R . . C4 C 0.96370(11) 0.6321(3) 0.33377(18) 0.0452(5) Uani 1 1 d . . . H4A H 0.9663 0.5412 0.3609 0.068 Uiso 1 1 calc R . . H4B H 0.9434 0.6864 0.3915 0.068 Uiso 1 1 calc R . . H4C H 1.0176 0.6617 0.3307 0.068 Uiso 1 1 calc R . . C5 C 0.78542(9) 0.62628(17) 0.29010(14) 0.0256(3) Uani 1 1 d . . . C6 C 0.71498(11) 0.40612(17) 0.23986(16) 0.0312(4) Uani 1 1 d . . . H6A H 0.7659 0.3561 0.2569 0.037 Uiso 1 1 calc R . . H6B H 0.6942 0.4144 0.1500 0.037 Uiso 1 1 calc R . . C7 C 0.65184(11) 0.33972(19) 0.29956(18) 0.0367(4) Uani 1 1 d . . . H7A H 0.6786 0.2857 0.3707 0.044 Uiso 1 1 calc R . . H7B H 0.6146 0.2843 0.2394 0.044 Uiso 1 1 calc R . . C8 C 0.60616(10) 0.45671(19) 0.34091(17) 0.0327(4) Uani 1 1 d . . . H8A H 0.5815 0.4311 0.4086 0.039 Uiso 1 1 calc R . . H8B H 0.5637 0.4903 0.2717 0.039 Uiso 1 1 calc R . . C9 C 0.67438(9) 0.56109(16) 0.38516(13) 0.0249(3) Uani 1 1 d . . . H9 H 0.6514 0.6510 0.3731 0.030 Uiso 1 1 calc R . . C10 C 0.71874(9) 0.53989(15) 0.52081(13) 0.0229(3) Uani 1 1 d . . . C11 C 0.79096(9) 0.47414(16) 0.55322(14) 0.0264(3) Uani 1 1 d . . . H11 H 0.8155 0.4464 0.4902 0.032 Uiso 1 1 calc R . . C12 C 0.83163(9) 0.44520(16) 0.68159(15) 0.0276(3) Uani 1 1 d . . . C13 C 0.72258(9) 0.56234(16) 0.74334(14) 0.0243(3) Uani 1 1 d . . . C14 C 0.69242(10) 0.60420(16) 0.84419(15) 0.0272(3) Uani 1 1 d . . . H14 H 0.7216 0.5882 0.9260 0.033 Uiso 1 1 calc R . . C15 C 0.61773(9) 0.67042(17) 0.81980(15) 0.0285(3) Uani 1 1 d . . . C16 C 0.57556(9) 0.69775(19) 0.69630(15) 0.0302(4) Uani 1 1 d . . . H16 H 0.5261 0.7439 0.6804 0.036 Uiso 1 1 calc R . . C17 C 0.60722(9) 0.65652(17) 0.59915(15) 0.0289(3) Uani 1 1 d . . . H17 H 0.5786 0.6752 0.5175 0.035 Uiso 1 1 calc R . . C18 C 0.68185(9) 0.58660(16) 0.61929(14) 0.0237(3) Uani 1 1 d . . . C19 C 0.62267(14) 0.7028(3) 1.03642(17) 0.0554(6) Uani 1 1 d . . . H19A H 0.6750 0.7461 1.0489 0.083 Uiso 1 1 calc R . . H19B H 0.6307 0.6108 1.0589 0.083 Uiso 1 1 calc R . . H19C H 0.5911 0.7445 1.0878 0.083 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 0.0309(6) 0.0334(6) 0.0332(6) -0.0053(5) 0.0162(5) -0.0034(5) O2 0.0374(6) 0.0278(6) 0.0453(7) -0.0081(5) 0.0186(6) -0.0030(5) O3 0.0279(6) 0.0387(7) 0.0429(7) 0.0069(6) 0.0062(5) 0.0085(5) O4 0.0282(5) 0.0318(6) 0.0274(5) 0.0032(5) 0.0050(4) 0.0048(5) O5 0.0415(6) 0.0497(8) 0.0268(6) -0.0023(5) 0.0134(5) 0.0098(6) N1 0.0286(6) 0.0238(7) 0.0258(6) -0.0020(5) 0.0116(5) 0.0004(5) C1 0.0291(8) 0.0350(9) 0.0371(9) 0.0026(7) 0.0158(7) -0.0012(7) C2 0.0436(10) 0.0625(14) 0.0448(10) -0.0055(10) 0.0271(9) -0.0020(10) C3 0.0532(12) 0.0445(13) 0.0807(16) 0.0241(11) 0.0311(12) 0.0009(10) C4 0.0336(9) 0.0597(14) 0.0434(11) -0.0005(9) 0.0113(8) -0.0013(9) C5 0.0253(7) 0.0263(8) 0.0262(7) 0.0018(6) 0.0082(6) 0.0028(6) C6 0.0350(8) 0.0254(8) 0.0362(9) -0.0071(7) 0.0144(7) -0.0009(6) C7 0.0356(9) 0.0311(9) 0.0459(11) -0.0048(7) 0.0148(8) -0.0065(7) C8 0.0259(8) 0.0387(10) 0.0344(9) -0.0058(7) 0.0093(7) -0.0032(7) C9 0.0256(7) 0.0247(8) 0.0258(7) 0.0013(6) 0.0093(6) 0.0036(6) C10 0.0230(7) 0.0203(7) 0.0265(7) 0.0010(6) 0.0084(6) -0.0022(5) C11 0.0265(7) 0.0261(8) 0.0287(8) 0.0027(6) 0.0110(6) 0.0026(6) C12 0.0258(8) 0.0241(8) 0.0337(9) 0.0035(6) 0.0087(6) -0.0005(6) C13 0.0236(7) 0.0213(7) 0.0276(7) 0.0007(6) 0.0053(6) -0.0017(6) C14 0.0322(8) 0.0272(8) 0.0218(7) 0.0022(6) 0.0054(6) -0.0005(6) C15 0.0318(8) 0.0287(8) 0.0278(8) -0.0024(6) 0.0122(7) -0.0010(7) C16 0.0230(7) 0.0364(9) 0.0318(8) -0.0029(7) 0.0076(6) 0.0045(7) C17 0.0249(7) 0.0358(9) 0.0249(8) -0.0005(6) 0.0041(6) 0.0015(7) C18 0.0236(7) 0.0228(7) 0.0255(7) -0.0003(6) 0.0072(6) -0.0022(6) C19 0.0626(13) 0.0790(17) 0.0258(9) -0.0037(10) 0.0128(9) 0.0220(12) _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 C5 1.3518(18) . ? O1 C1 1.4742(19) . ? O2 C5 1.213(2) . ? O3 C12 1.2060(19) . ? O4 C13 1.3772(18) . ? O4 C12 1.384(2) . ? O5 C15 1.3526(19) . ? O5 C19 1.425(2) . ? N1 C5 1.352(2) . ? N1 C9 1.4576(18) . ? N1 C6 1.463(2) . ? C1 C3 1.512(3) . ? C1 C2 1.514(3) . ? C1 C4 1.524(2) . ? C6 C7 1.528(2) . ? C7 C8 1.532(3) . ? C8 C9 1.544(2) . ? C9 C10 1.514(2) . ? C10 C11 1.351(2) . ? C10 C18 1.449(2) . ? C11 C12 1.443(2) . ? C13 C14 1.391(2) . ? C13 C18 1.393(2) . ? C14 C15 1.388(2) . ? C15 C16 1.400(2) . ? C16 C17 1.367(2) . ? C17 C18 1.407(2) . ? 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 C5 O1 C1 119.44(13) . . ? C13 O4 C12 121.35(12) . . ? C15 O5 C19 118.48(14) . . ? C5 N1 C9 120.11(13) . . ? C5 N1 C6 126.01(13) . . ? C9 N1 C6 113.63(12) . . ? O1 C1 C3 110.36(15) . . ? O1 C1 C2 102.54(15) . . ? C3 C1 C2 112.18(17) . . ? O1 C1 C4 109.02(13) . . ? C3 C1 C4 112.06(18) . . ? C2 C1 C4 110.25(15) . . ? O2 C5 O1 126.35(15) . . ? O2 C5 N1 123.99(14) . . ? O1 C5 N1 109.66(13) . . ? N1 C6 C7 103.60(13) . . ? C6 C7 C8 103.86(14) . . ? C7 C8 C9 103.33(13) . . ? N1 C9 C10 112.39(12) . . ? N1 C9 C8 101.63(12) . . ? C10 C9 C8 111.50(13) . . ? C11 C10 C18 118.59(13) . . ? C11 C10 C9 121.76(13) . . ? C18 C10 C9 119.60(12) . . ? C10 C11 C12 122.71(14) . . ? O3 C12 O4 116.83(15) . . ? O3 C12 C11 126.04(15) . . ? O4 C12 C11 117.13(13) . . ? O4 C13 C14 115.74(13) . . ? O4 C13 C18 121.48(13) . . ? C14 C13 C18 122.78(14) . . ? C15 C14 C13 118.43(14) . . ? O5 C15 C14 124.89(15) . . ? O5 C15 C16 114.82(14) . . ? C14 C15 C16 120.29(14) . . ? C17 C16 C15 119.88(14) . . ? C16 C17 C18 121.80(14) . . ? C13 C18 C17 116.78(13) . . ? C13 C18 C10 118.58(13) . . ? C17 C18 C10 124.64(13) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.169 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.039