# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 loop_ _publ_author_name 'Sally Brooker' 'David Larsen' 'Rongqing Li' _publ_contact_author_name 'Dr Sally Brooker' _publ_contact_author_address ; Department of Chemistry University of Otago PO Box 56 Dunedin NEW ZEALAND ; _publ_contact_author_email SBROOKER@ALKALI.OTAGO.AC.NZ _publ_section_title ; Syntheses, Structures and Tautomers of 2,5-Disubstituted Pyrroles ; data_pda _database_code_CSD 207581 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H9 N O4' _chemical_formula_weight 183.16 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 8.333(3) _cell_length_b 12.671(4) _cell_length_c 7.960(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.191(5) _cell_angle_gamma 90.00 _cell_volume 840.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 168(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type Semi-empirical(SADABS) _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 168(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 'Bruker SMART area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5612 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 26.45 _reflns_number_total 1696 _reflns_number_gt 1205 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0552P)^2^+0.2892P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1696 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0735 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1211 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 N1 N 0.1231(2) 0.13295(11) 0.3671(2) 0.0291(4) Uani 1 1 d . . . H1 H 0.0423 0.1411 0.2759 0.035 Uiso 1 1 d . . . C2 C 0.0713(2) 0.13193(13) 0.5303(3) 0.0291(5) Uani 1 1 d . . . C3 C 0.2028(3) 0.11968(14) 0.6330(3) 0.0341(5) Uani 1 1 d . . . H3 H 0.2062 0.1154 0.7605 0.041 Uiso 1 1 d . . . C4 C 0.3395(3) 0.11212(15) 0.5300(3) 0.0343(5) Uani 1 1 d . . . H4 H 0.4601 0.1071 0.5742 0.041 Uiso 1 1 d . . . C5 C 0.2868(2) 0.12131(13) 0.3673(3) 0.0292(5) Uani 1 1 d . . . C6 C 0.3769(3) 0.11322(14) 0.2064(3) 0.0357(5) Uani 1 1 d . . . H6A H 0.3572 0.1760 0.1348 0.043 Uiso 1 1 d . . . H6B H 0.5015 0.1159 0.2316 0.043 Uiso 1 1 d . . . C7 C 0.3324(3) 0.01199(14) 0.1207(2) 0.0293(5) Uani 1 1 d . . . O1 O 0.41328(18) -0.06832(10) 0.13445(19) 0.0385(4) Uani 1 1 d . . . O2 O 0.19623(19) 0.01568(10) 0.03700(19) 0.0382(4) Uani 1 1 d . . . H20 H 0.1749 -0.0536 -0.0167 0.046 Uiso 1 1 d . . . C16 C -0.1030(3) 0.13945(15) 0.5695(3) 0.0355(5) Uani 1 1 d . . . H16A H -0.1673 0.0822 0.5102 0.043 Uiso 1 1 d . . . H16B H -0.1140 0.1262 0.7055 0.043 Uiso 1 1 d . . . C17 C -0.1744(2) 0.24604(14) 0.5316(3) 0.0297(5) Uani 1 1 d . . . O3 O -0.11235(18) 0.32800(10) 0.58130(19) 0.0417(4) Uani 1 1 d . . . O4 O -0.30562(19) 0.24423(11) 0.4408(2) 0.0442(4) Uani 1 1 d . . . H40 H -0.3494 0.3279 0.4135 0.053 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0361(10) 0.0243(8) 0.0269(9) 0.0012(6) 0.0015(7) 0.0000(6) C2 0.0418(12) 0.0197(9) 0.0262(11) 0.0015(7) 0.0072(9) 0.0007(8) C3 0.0483(14) 0.0261(10) 0.0279(11) -0.0008(8) 0.0000(10) 0.0012(9) C4 0.0401(13) 0.0267(10) 0.0358(13) -0.0031(8) -0.0051(10) 0.0012(8) C5 0.0339(12) 0.0214(9) 0.0324(12) -0.0016(8) 0.0042(9) -0.0013(8) C6 0.0440(13) 0.0278(10) 0.0358(13) -0.0025(9) 0.0103(10) -0.0060(9) C7 0.0358(12) 0.0275(10) 0.0250(11) 0.0022(8) 0.0095(9) -0.0017(8) O1 0.0429(9) 0.0285(7) 0.0442(9) -0.0010(6) 0.0034(7) 0.0032(6) O2 0.0491(10) 0.0284(7) 0.0370(9) -0.0023(6) -0.0038(7) 0.0025(6) C16 0.0410(13) 0.0241(9) 0.0419(13) 0.0033(8) 0.0104(10) 0.0000(8) C17 0.0343(12) 0.0257(9) 0.0294(11) -0.0011(8) 0.0089(9) -0.0019(8) O3 0.0514(10) 0.0254(7) 0.0477(10) -0.0007(6) -0.0118(7) -0.0012(6) O4 0.0446(10) 0.0290(7) 0.0588(11) -0.0053(7) -0.0076(8) -0.0027(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 N1 C5 1.372(3) . ? N1 C2 1.378(3) . ? C2 C3 1.362(3) . ? C2 C16 1.495(3) . ? C3 C4 1.421(3) . ? C4 C5 1.364(3) . ? C5 C6 1.502(3) . ? C6 C7 1.496(3) . ? C7 O1 1.224(2) . ? C7 O2 1.305(3) . ? C16 C17 1.504(3) . ? C17 O3 1.222(2) . ? C17 O4 1.298(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 C5 N1 C2 109.18(17) . . ? C3 C2 N1 107.66(18) . . ? C3 C2 C16 130.92(19) . . ? N1 C2 C16 121.38(19) . . ? C2 C3 C4 107.83(19) . . ? C5 C4 C3 107.18(19) . . ? C4 C5 N1 108.14(18) . . ? C4 C5 C6 130.3(2) . . ? N1 C5 C6 121.40(18) . . ? C7 C6 C5 108.88(15) . . ? O1 C7 O2 123.14(18) . . ? O1 C7 C6 122.8(2) . . ? O2 C7 C6 114.02(17) . . ? C2 C16 C17 113.41(15) . . ? O3 C17 O4 122.75(18) . . ? O3 C17 C16 122.36(19) . . ? O4 C17 C16 114.89(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C2 C3 0.0(2) . . . . ? C5 N1 C2 C16 -177.89(15) . . . . ? N1 C2 C3 C4 -0.4(2) . . . . ? C16 C2 C3 C4 177.20(17) . . . . ? C2 C3 C4 C5 0.7(2) . . . . ? C3 C4 C5 N1 -0.7(2) . . . . ? C3 C4 C5 C6 -176.23(18) . . . . ? C2 N1 C5 C4 0.43(19) . . . . ? C2 N1 C5 C6 176.44(15) . . . . ? C4 C5 C6 C7 107.9(2) . . . . ? N1 C5 C6 C7 -67.1(2) . . . . ? C5 C6 C7 O1 -96.5(2) . . . . ? C5 C6 C7 O2 80.4(2) . . . . ? C3 C2 C16 C17 113.1(2) . . . . ? N1 C2 C16 C17 -69.5(2) . . . . ? C2 C16 C17 O3 -50.1(3) . . . . ? C2 C16 C17 O4 129.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.156 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.054 data_pdest _database_code_CSD 207582 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H17 N O4' _chemical_formula_weight 239.27 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 9.089(3) _cell_length_b 13.036(4) _cell_length_c 10.604(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.047(4) _cell_angle_gamma 90.00 _cell_volume 1237.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.63 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type 'Semi-empirical (SADABS)' _exptl_absorpt_correction_T_min 0.53 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 'Bruker SMART area detector' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15210 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0138 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.47 _reflns_number_total 2536 _reflns_number_gt 2276 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0477P)^2^+0.3330P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2536 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0967 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 N1 N 1.06885(10) 0.92285(7) 0.39197(9) 0.0283(2) Uani 1 1 d . . . H1 H 1.0750 0.9846 0.3513 0.034 Uiso 1 1 d . . . C2 C 1.15855(12) 0.90157(9) 0.50666(11) 0.0293(2) Uani 1 1 d . . . C3 C 1.11058(14) 0.79930(9) 0.55140(12) 0.0368(3) Uani 1 1 d . . . H3A H 1.1968 0.7523 0.5800 0.044 Uiso 1 1 d . . . H3B H 1.0578 0.8099 0.6298 0.044 Uiso 1 1 d . . . C4 C 0.99922(13) 0.75712(9) 0.43782(12) 0.0343(3) Uani 1 1 d . . . H4A H 0.9055 0.7355 0.4623 0.041 Uiso 1 1 d . . . H4B H 1.0431 0.7001 0.3951 0.041 Uiso 1 1 d . . . C5 C 0.97157(12) 0.84580(8) 0.34568(11) 0.0283(2) Uani 1 1 d . . . C6 C 0.87157(12) 0.84948(8) 0.23617(11) 0.0306(2) Uani 1 1 d . . . H6 H 0.8096 0.7923 0.2083 0.037 Uiso 1 1 d . . . C7 C 0.85713(12) 0.93891(9) 0.15472(11) 0.0304(2) Uani 1 1 d . . . O1 O 0.92840(10) 1.01834(6) 0.17494(8) 0.0387(2) Uani 1 1 d . . . O2 O 0.75357(9) 0.92540(6) 0.04830(8) 0.0352(2) Uani 1 1 d . . . C8 C 0.74063(15) 1.00765(10) -0.04439(12) 0.0400(3) Uani 1 1 d . . . H8A H 0.8373 1.0187 -0.0732 0.048 Uiso 1 1 calc R . . H8B H 0.7115 1.0722 -0.0061 0.048 Uiso 1 1 calc R . . C9 C 0.62409(19) 0.97675(13) -0.15425(15) 0.0597(4) Uani 1 1 d . . . H9A H 0.6538 0.9125 -0.1907 0.072 Uiso 1 1 calc R . . H9B H 0.6129 1.0306 -0.2198 0.072 Uiso 1 1 calc R . . H9C H 0.5288 0.9668 -0.1246 0.072 Uiso 1 1 calc R . . C16 C 1.26867(12) 0.96208(9) 0.56693(11) 0.0311(3) Uani 1 1 d . . . H16 H 1.3268 0.9397 0.6482 0.037 Uiso 1 1 d . . . C17 C 1.30370(12) 1.06062(9) 0.51716(11) 0.0301(2) Uani 1 1 d . . . O3 O 1.23605(9) 1.10215(7) 0.42162(8) 0.0374(2) Uani 1 1 d . . . O4 O 1.42358(9) 1.10378(6) 0.59094(8) 0.0343(2) Uani 1 1 d . . . C18 C 1.46754(14) 1.20396(9) 0.55320(12) 0.0376(3) Uani 1 1 d . . . H18A H 1.3822 1.2521 0.5444 0.045 Uiso 1 1 calc R . . H18B H 1.5030 1.2001 0.4702 0.045 Uiso 1 1 calc R . . C19 C 1.59158(15) 1.23913(10) 0.65744(14) 0.0424(3) Uani 1 1 d . . . H19A H 1.5536 1.2453 0.7381 0.051 Uiso 1 1 calc R . . H19B H 1.6286 1.3060 0.6344 0.051 Uiso 1 1 calc R . . H19C H 1.6732 1.1890 0.6676 0.051 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 N1 0.0299(5) 0.0253(5) 0.0280(5) 0.0004(4) 0.0001(4) 0.0003(4) C2 0.0298(5) 0.0288(6) 0.0285(5) 0.0007(4) 0.0032(4) 0.0064(4) C3 0.0398(6) 0.0324(6) 0.0351(6) 0.0058(5) -0.0023(5) -0.0008(5) C4 0.0360(6) 0.0274(6) 0.0372(6) 0.0030(5) 0.0002(5) 0.0011(4) C5 0.0295(5) 0.0245(5) 0.0314(6) -0.0019(4) 0.0065(4) 0.0022(4) C6 0.0327(6) 0.0270(5) 0.0307(6) -0.0028(4) 0.0020(4) -0.0023(4) C7 0.0321(6) 0.0313(6) 0.0267(5) -0.0034(4) 0.0023(4) -0.0004(4) O1 0.0466(5) 0.0319(4) 0.0343(5) 0.0022(3) -0.0024(4) -0.0083(4) O2 0.0407(5) 0.0318(4) 0.0294(4) 0.0020(3) -0.0041(3) -0.0035(3) C8 0.0466(7) 0.0365(6) 0.0343(6) 0.0069(5) 0.0001(5) -0.0012(5) C9 0.0716(10) 0.0581(9) 0.0407(8) 0.0139(7) -0.0144(7) -0.0104(8) C16 0.0306(5) 0.0320(6) 0.0282(5) 0.0004(4) -0.0012(4) 0.0041(4) C17 0.0280(5) 0.0316(6) 0.0290(6) -0.0043(4) 0.0009(4) 0.0035(4) O3 0.0397(5) 0.0343(4) 0.0337(4) 0.0037(3) -0.0064(4) -0.0004(4) O4 0.0321(4) 0.0321(4) 0.0350(4) 0.0014(3) -0.0043(3) -0.0022(3) C18 0.0380(6) 0.0308(6) 0.0418(7) 0.0013(5) 0.0004(5) -0.0014(5) C19 0.0384(7) 0.0378(7) 0.0485(8) -0.0043(6) 0.0007(6) -0.0051(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 N1 C2 1.3692(14) . ? N1 C5 1.3711(14) . ? C2 C16 1.3451(16) . ? C2 C3 1.5048(16) . ? C3 C4 1.5337(17) . ? C4 C5 1.5062(16) . ? C5 C6 1.3449(16) . ? C6 C7 1.4431(16) . ? C7 O1 1.2204(14) . ? C7 O2 1.3490(14) . ? O2 C8 1.4453(15) . ? C8 C9 1.4869(19) . ? C16 C17 1.4451(17) . ? C17 O3 1.2166(14) . ? C17 O4 1.3485(14) . ? O4 C18 1.4425(15) . ? C18 C19 1.5060(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C5 114.61(9) . . ? C16 C2 N1 125.56(11) . . ? C16 C2 C3 127.03(11) . . ? N1 C2 C3 107.41(10) . . ? C2 C3 C4 104.94(9) . . ? C5 C4 C3 104.29(9) . . ? C6 C5 N1 125.41(10) . . ? C6 C5 C4 126.78(10) . . ? N1 C5 C4 107.80(10) . . ? C5 C6 C7 121.52(10) . . ? O1 C7 O2 121.95(11) . . ? O1 C7 C6 126.17(11) . . ? O2 C7 C6 111.88(10) . . ? C7 O2 C8 115.73(9) . . ? O2 C8 C9 107.11(11) . . ? C2 C16 C17 122.74(10) . . ? O3 C17 O4 122.50(11) . . ? O3 C17 C16 126.02(11) . . ? O4 C17 C16 111.48(10) . . ? C17 O4 C18 116.85(9) . . ? O4 C18 C19 106.26(10) . . ? 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 C5 N1 C2 C16 175.58(11) . . . . ? C5 N1 C2 C3 -4.54(13) . . . . ? C16 C2 C3 C4 -171.35(11) . . . . ? N1 C2 C3 C4 8.77(12) . . . . ? C2 C3 C4 C5 -9.53(12) . . . . ? C2 N1 C5 C6 179.08(11) . . . . ? C2 N1 C5 C4 -1.89(13) . . . . ? C3 C4 C5 C6 -173.73(11) . . . . ? C3 C4 C5 N1 7.25(12) . . . . ? N1 C5 C6 C7 -0.24(18) . . . . ? C4 C5 C6 C7 -179.09(11) . . . . ? C5 C6 C7 O1 -1.07(19) . . . . ? C5 C6 C7 O2 178.24(10) . . . . ? O1 C7 O2 C8 4.52(16) . . . . ? C6 C7 O2 C8 -174.82(10) . . . . ? C7 O2 C8 C9 178.78(11) . . . . ? N1 C2 C16 C17 1.43(18) . . . . ? C3 C2 C16 C17 -178.43(11) . . . . ? C2 C16 C17 O3 3.83(19) . . . . ? C2 C16 C17 O4 -176.50(10) . . . . ? O3 C17 O4 C18 1.32(16) . . . . ? C16 C17 O4 C18 -178.36(10) . . . . ? C17 O4 C18 C19 174.10(10) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.47 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.179 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.048