# Electronic Supplementary Material (ESI) for Analytical Methods # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_bi2a _database_code_depnum_ccdc_archive 'CCDC 760142' #TrackingRef '- 2A.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common 'isophorone diammonium squarate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H24 N2 O4' _chemical_formula_weight 284.35 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 Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 13.520(3) _cell_length_b 8.4840(19) _cell_length_c 13.632(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1563.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9757 _exptl_absorpt_correction_T_max 0.9886 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8444 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.14 _reflns_number_total 2478 _reflns_number_gt 1936 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _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^)+(0.0551P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment Constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.4(15) _refine_ls_number_reflns 2478 _refine_ls_number_parameters 186 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0592 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1099 _refine_ls_wR_factor_gt 0.1028 _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_restrained_S_all 0.990 _refine_ls_shift/su_max 0.014 _refine_ls_shift/su_mean 0.006 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 1.23853(17) 0.2676(3) 0.7516(2) 0.0643(7) Uani 1 1 d . . . O2 O 1.06442(16) 0.4723(2) 0.64981(16) 0.0516(6) Uani 1 1 d . . . O3 O 1.17099(15) 0.3972(3) 0.96420(15) 0.0506(6) Uani 1 1 d . . . O5 O 1.00180(17) 0.6149(2) 0.85432(17) 0.0599(6) Uani 1 1 d . . . C8 C 0.86687(18) -0.1286(3) 1.0165(2) 0.0321(6) Uani 1 1 d . . . H2 H 0.8126 -0.1061 1.0621 0.039 Uiso 1 1 calc R . . C1 C 1.06624(19) 0.5146(3) 0.8310(2) 0.0375(7) Uani 1 1 d . . . C2 C 1.14241(18) 0.4199(3) 0.8776(2) 0.0368(7) Uani 1 1 d . . . C3 C 1.1730(2) 0.3603(3) 0.7822(2) 0.0396(7) Uani 1 1 d . . . C4 C 1.09553(19) 0.4538(3) 0.7359(2) 0.0358(7) Uani 1 1 d . . . C5 C 0.96344(18) -0.0826(3) 1.0650(2) 0.0344(6) Uani 1 1 d . . . H5A H 1.0177 -0.1051 1.0207 0.041 Uiso 1 1 calc R . . H5B H 0.9727 -0.1456 1.1237 0.041 Uiso 1 1 calc R . . C6 C 0.96558(18) 0.0933(3) 1.0927(2) 0.0349(6) Uani 1 1 d . . . C7 C 1.0721(2) 0.1299(3) 1.1235(2) 0.0403(7) Uani 1 1 d . . . H7A H 1.0877 0.0682 1.1814 0.048 Uiso 1 1 calc R . . H7B H 1.1162 0.0959 1.0715 0.048 Uiso 1 1 calc R . . C9 C 0.8504(2) -0.0341(3) 0.9231(2) 0.0461(7) Uani 1 1 d . . . H9A H 0.9027 -0.0587 0.8769 0.055 Uiso 1 1 calc R . . H9B H 0.7882 -0.0661 0.8939 0.055 Uiso 1 1 calc R . . C10 C 0.8485(2) 0.1424(3) 0.9400(2) 0.0464(8) Uani 1 1 d . . . C11 C 0.94023(19) 0.1913(3) 1.0010(2) 0.0370(7) Uani 1 1 d . . . H11A H 0.9972 0.1892 0.9578 0.044 Uiso 1 1 calc R . . H11B H 0.9310 0.2998 1.0215 0.044 Uiso 1 1 calc R . . C12 C 0.8969(2) 0.1229(4) 1.1808(2) 0.0519(8) Uani 1 1 d . . . H12A H 0.9291 0.0890 1.2400 0.078 Uiso 1 1 calc R . . H12B H 0.8366 0.0648 1.1722 0.078 Uiso 1 1 calc R . . H12C H 0.8822 0.2334 1.1852 0.078 Uiso 1 1 calc R . . C13 C 0.8551(3) 0.2268(4) 0.8400(3) 0.0757(13) Uani 1 1 d . . . H13A H 0.8008 0.1945 0.7994 0.114 Uiso 1 1 calc R . . H13B H 0.9163 0.1996 0.8086 0.114 Uiso 1 1 calc R . . H13C H 0.8524 0.3387 0.8499 0.114 Uiso 1 1 calc R . . C14 C 0.7510(2) 0.1928(3) 0.9895(4) 0.0739(12) Uani 1 1 d . . . H14A H 0.6970 0.1760 0.9450 0.111 Uiso 1 1 calc R . . H14B H 0.7545 0.3025 1.0064 0.111 Uiso 1 1 calc R . . H14C H 0.7409 0.1314 1.0478 0.111 Uiso 1 1 calc R . . N1 N 1.09232(17) 0.2981(3) 1.1451(2) 0.0482(7) Uani 1 1 d . . . H8A H 1.1002 0.3506 1.0891 0.072 Uiso 1 1 calc R . . H8B H 1.1471 0.3059 1.1809 0.072 Uiso 1 1 calc R . . H8C H 1.0417 0.3389 1.1782 0.072 Uiso 1 1 calc R . . N2 N 0.86694(15) -0.3005(2) 0.99483(17) 0.0348(5) Uani 1 1 d . . . H2A H 0.9091 -0.3203 0.9462 0.052 Uiso 1 1 calc R . . H2B H 0.8064 -0.3305 0.9772 0.052 Uiso 1 1 calc R . . H2C H 0.8854 -0.3535 1.0481 0.052 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 0.0532(13) 0.0653(14) 0.0743(16) 0.0119(13) 0.0241(12) 0.0322(12) O2 0.0706(14) 0.0471(11) 0.0370(13) 0.0014(10) -0.0056(11) 0.0165(10) O3 0.0451(12) 0.0652(14) 0.0416(13) 0.0040(11) -0.0052(10) -0.0005(10) O5 0.0586(13) 0.0576(13) 0.0637(16) 0.0029(12) 0.0185(12) 0.0263(11) C8 0.0292(13) 0.0313(13) 0.0358(16) -0.0012(13) 0.0009(12) -0.0012(10) C1 0.0335(15) 0.0358(14) 0.0433(18) 0.0015(14) 0.0081(13) 0.0039(13) C2 0.0275(13) 0.0406(16) 0.0423(19) 0.0032(14) 0.0010(13) -0.0018(11) C3 0.0302(15) 0.0416(15) 0.0469(19) 0.0067(14) 0.0077(14) 0.0042(13) C4 0.0394(15) 0.0282(13) 0.0399(19) 0.0028(13) 0.0042(15) 0.0029(11) C5 0.0313(15) 0.0338(13) 0.0381(18) -0.0021(12) -0.0059(12) 0.0003(11) C6 0.0293(14) 0.0383(14) 0.0370(16) -0.0053(12) -0.0031(12) -0.0014(11) C7 0.0361(15) 0.0396(15) 0.0450(19) -0.0065(13) -0.0057(13) -0.0022(12) C9 0.0476(17) 0.0424(15) 0.0483(19) 0.0006(15) -0.0145(15) -0.0094(14) C10 0.0421(17) 0.0377(15) 0.060(2) 0.0091(14) -0.0193(15) -0.0070(13) C11 0.0346(14) 0.0312(13) 0.0452(18) -0.0010(13) -0.0056(13) -0.0015(11) C12 0.0517(18) 0.0545(18) 0.049(2) -0.0169(17) 0.0146(16) -0.0107(15) C13 0.097(3) 0.058(2) 0.073(3) 0.019(2) -0.044(2) -0.021(2) C14 0.0398(17) 0.0470(18) 0.135(4) 0.004(2) -0.021(2) 0.0060(16) N1 0.0316(13) 0.0504(15) 0.0628(18) -0.0170(14) -0.0038(12) -0.0038(10) N2 0.0352(12) 0.0318(11) 0.0376(14) -0.0022(10) -0.0021(11) -0.0025(9) _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 C3 1.256(3) . ? O2 C4 1.256(3) . ? O3 C2 1.257(3) . ? O5 C1 1.258(3) . ? C8 N2 1.488(3) . ? C8 C5 1.515(4) . ? C8 C9 1.521(4) . ? C8 H2 0.9800 . ? C1 C4 1.451(4) . ? C1 C2 1.452(4) . ? C2 C3 1.456(4) . ? C3 C4 1.458(4) . ? C5 C6 1.540(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.532(4) . ? C6 C12 1.538(4) . ? C6 C11 1.541(4) . ? C7 N1 1.483(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C9 C10 1.515(4) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C14 1.541(5) . ? C10 C13 1.542(5) . ? C10 C11 1.550(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? N1 H8A 0.8900 . ? N1 H8B 0.8900 . ? N1 H8C 0.8900 . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? 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 N2 C8 C5 109.80(19) . . ? N2 C8 C9 110.5(2) . . ? C5 C8 C9 110.8(2) . . ? N2 C8 H2 108.5 . . ? C5 C8 H2 108.6 . . ? C9 C8 H2 108.5 . . ? O5 C1 C4 130.9(3) . . ? O5 C1 C2 139.0(3) . . ? C4 C1 C2 90.0(2) . . ? O3 C2 C1 135.5(3) . . ? O3 C2 C3 134.3(3) . . ? C1 C2 C3 90.2(2) . . ? O1 C3 C2 135.7(3) . . ? O1 C3 C4 134.7(3) . . ? C2 C3 C4 89.6(2) . . ? O2 C4 C1 134.4(2) . . ? O2 C4 C3 135.5(3) . . ? C1 C4 C3 90.1(2) . . ? C8 C5 C6 111.9(2) . . ? C8 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C8 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C7 C6 C12 108.7(2) . . ? C7 C6 C5 106.3(2) . . ? C12 C6 C5 109.8(2) . . ? C7 C6 C11 108.8(2) . . ? C12 C6 C11 114.3(2) . . ? C5 C6 C11 108.6(2) . . ? N1 C7 C6 115.0(2) . . ? N1 C7 H7A 108.5 . . ? C6 C7 H7A 108.5 . . ? N1 C7 H7B 108.5 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C10 C9 C8 113.4(2) . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? C8 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 C14 110.8(2) . . ? C9 C10 C13 108.9(3) . . ? C14 C10 C13 107.9(3) . . ? C9 C10 C11 109.4(2) . . ? C14 C10 C11 112.1(3) . . ? C13 C10 C11 107.6(2) . . ? C6 C11 C10 118.0(2) . . ? C6 C11 H11A 107.8 . . ? C10 C11 H11A 107.8 . . ? C6 C11 H11B 107.8 . . ? C10 C11 H11B 107.8 . . ? H11A C11 H11B 107.2 . . ? C6 C12 H12A 109.5 . . ? C6 C12 H12B 109.4 . . ? H12A C12 H12B 109.5 . . ? C6 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.4 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 N1 H8A 109.5 . . ? C7 N1 H8B 109.5 . . ? H8A N1 H8B 109.5 . . ? C7 N1 H8C 109.4 . . ? H8A N1 H8C 109.5 . . ? H8B N1 H8C 109.5 . . ? C8 N2 H2A 109.4 . . ? C8 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C8 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.14 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.141 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.039 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_bi161 _database_code_depnum_ccdc_archive 'CCDC 882497' #TrackingRef '- 161.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 N2 O14' _chemical_formula_weight 526.41 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/c' _symmetry_space_group_name_Hall '- P 2ybc' 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 6.6876(10) _cell_length_b 25.062(4) _cell_length_c 13.824(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.293(5) _cell_angle_gamma 90.00 _cell_volume 2292.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.525 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.131 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9656 _exptl_absorpt_correction_T_max 0.9768 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14192 _diffrn_reflns_av_R_equivalents 0.0607 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 25.04 _reflns_number_total 4023 _reflns_number_gt 2526 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker GIS' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _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^)+(0.0696P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4023 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1043 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.1717 _refine_ls_wR_factor_gt 0.1553 _refine_ls_goodness_of_fit_ref 1.196 _refine_ls_restrained_S_all 1.196 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.007 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 -0.2250(4) 0.77463(9) 1.14874(15) 0.0457(7) Uani 1 1 d . . . H1 H -0.2088 0.7585 1.2026 0.069 Uiso 1 1 calc R . . O1S O -0.0429(5) 0.57313(11) 0.9121(2) 0.0495(7) Uani 1 1 d . . . O2 O -0.2278(4) 1.00315(9) 0.83085(18) 0.0536(7) Uani 1 1 d . . . O3 O -0.1300(4) 0.84473(9) 1.24390(16) 0.0453(6) Uani 1 1 d . . . O4 O -0.2270(4) 0.77393(9) 0.81658(16) 0.0421(6) Uani 1 1 d . . . O5 O -0.2622(4) 0.84290(10) 0.71830(16) 0.0454(6) Uani 1 1 d . . . O6 O -0.2601(4) 0.93824(11) 0.72373(17) 0.0494(7) Uani 1 1 d . . . O7 O 0.2585(4) 0.77239(9) 1.03277(15) 0.0452(6) Uani 1 1 d . . . H2 H 0.2746 0.7569 1.0872 0.068 Uiso 1 1 calc R . . O8 O 0.2521(4) 1.00456(10) 0.71946(19) 0.0585(8) Uani 1 1 d . . . O9 O 0.1926(4) 0.94121(11) 0.61044(18) 0.0602(8) Uani 1 1 d . . . O10 O 0.1642(4) 0.84591(10) 0.60028(16) 0.0497(7) Uani 1 1 d . . . O11 O 0.2566(4) 0.77696(10) 0.69454(16) 0.0531(7) Uani 1 1 d . . . O12 O 0.3323(4) 0.84356(9) 1.12627(16) 0.0457(6) Uani 1 1 d . . . C1 C -0.2335(5) 0.95564(13) 0.8118(2) 0.0337(8) Uani 1 1 d . . . C2 C -0.2393(5) 0.82319(13) 0.8037(2) 0.0309(8) Uani 1 1 d . . . C3 C 0.2961(5) 0.82311(13) 1.0455(2) 0.0311(7) Uani 1 1 d . . . C4 C 0.2901(4) 0.85456(12) 0.9539(2) 0.0258(7) Uani 1 1 d . . . C5 C 0.2227(5) 0.82511(14) 0.6839(2) 0.0326(8) Uani 1 1 d . . . C6 C 0.4497(5) 0.66323(14) 0.8939(3) 0.0445(9) Uani 1 1 d . . . H3 H 0.4603 0.6893 0.8410 0.053 Uiso 1 1 calc R . . H4 H 0.3168 0.6685 0.9160 0.053 Uiso 1 1 calc R . . C7 C -0.1762(4) 0.82483(12) 1.1629(2) 0.0298(7) Uani 1 1 d . . . C8 C -0.1853(4) 0.85639(12) 1.0712(2) 0.0247(7) Uani 1 1 d . . . C9 C -0.2094(4) 0.83160(12) 0.9813(2) 0.0262(7) Uani 1 1 d . . . H5 H -0.2184 0.7938 0.9793 0.031 Uiso 1 1 calc R . . C10 C -0.2213(4) 0.85928(12) 0.8931(2) 0.0237(7) Uani 1 1 d . . . C11 C -0.2122(4) 0.91571(12) 0.8969(2) 0.0235(7) Uani 1 1 d . . . C12 C -0.1841(4) 0.94030(12) 0.9885(2) 0.0286(7) Uani 1 1 d . . . H6 H -0.1746 0.9781 0.9917 0.034 Uiso 1 1 calc R . . C13 C -0.1697(4) 0.91175(12) 1.0745(2) 0.0300(7) Uani 1 1 d . . . H7 H -0.1493 0.9298 1.1356 0.036 Uiso 1 1 calc R . . C14 C 0.2639(4) 0.83011(13) 0.8629(2) 0.0285(7) Uani 1 1 d . . . H8 H 0.2557 0.7923 0.8594 0.034 Uiso 1 1 calc R . . C15 C 0.2492(4) 0.85961(12) 0.7756(2) 0.0261(7) Uani 1 1 d . . . C16 C 0.2605(4) 0.91579(12) 0.7820(2) 0.0278(7) Uani 1 1 d . . . C17 C 0.2360(5) 0.95693(14) 0.6997(3) 0.0394(8) Uani 1 1 d . . . C18 C 0.3071(4) 0.90969(13) 0.9595(2) 0.0303(7) Uani 1 1 d . . . H9 H 0.3281 0.9268 1.0214 0.036 Uiso 1 1 calc R . . C19 C 0.2934(4) 0.93961(13) 0.8750(2) 0.0308(8) Uani 1 1 d . . . H10 H 0.3067 0.9773 0.8798 0.037 Uiso 1 1 calc R . . N1 N 0.2722(5) 0.59377(13) 0.7859(2) 0.0398(8) Uani 1 1 d . . . H1A H 0.174(5) 0.6173(14) 0.775(3) 0.048 Uiso 1 1 calc . . . H1B H 0.259(5) 0.5623(15) 0.757(3) 0.048 Uiso 1 1 calc . . . C20 C 0.4578(5) 0.60701(13) 0.8524(3) 0.0440(9) Uani 1 1 d . . . H14 H 0.5753 0.6041 0.8165 0.053 Uiso 1 1 calc R . . H15 H 0.4768 0.5810 0.9068 0.053 Uiso 1 1 calc R . . C21 C 0.6134(5) 0.67488(15) 0.9780(3) 0.0483(10) Uani 1 1 d . . . H17 H 0.5826 0.7091 1.0085 0.058 Uiso 1 1 calc R . . H18 H 0.6132 0.6465 1.0278 0.058 Uiso 1 1 calc R . . N2 N 0.8181(5) 0.67825(12) 0.9488(2) 0.0420(8) Uani 1 1 d . . . H2A H 0.834(5) 0.6736(14) 0.887(3) 0.050 Uiso 1 1 calc . . . H2B H 0.924(5) 0.6849(14) 0.993(3) 0.050 Uiso 1 1 calc . . . OS2 O 0.3711(14) 0.4892(6) 0.9579(9) 0.109(4) Uani 0.50 1 d P . . OS3 O 0.2476(14) 0.4869(5) 0.9524(8) 0.094(3) Uani 0.50 1 d P . . H22 H -0.112(5) 0.5509(15) 0.867(3) 0.051(11) Uiso 1 1 d . . . H23 H -0.257(6) 0.895(2) 0.724(3) 0.076(14) Uiso 1 1 d . . . H24 H 0.175(7) 0.897(2) 0.612(4) 0.111(18) Uiso 1 1 d . . . H25 H 0.031(9) 0.546(2) 0.934(4) 0.13(2) 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 O1 0.0837(18) 0.0273(14) 0.0234(12) 0.0056(10) -0.0018(12) -0.0076(13) O1S 0.0617(17) 0.0365(17) 0.0462(17) -0.0044(13) -0.0057(14) 0.0006(14) O2 0.090(2) 0.0226(14) 0.0455(16) 0.0115(11) 0.0000(14) -0.0004(13) O3 0.0709(17) 0.0398(15) 0.0229(13) -0.0017(10) -0.0006(11) -0.0100(12) O4 0.0716(17) 0.0264(14) 0.0268(12) -0.0065(10) 0.0025(11) 0.0027(12) O5 0.0744(18) 0.0385(15) 0.0220(13) -0.0016(11) 0.0026(11) 0.0033(12) O6 0.083(2) 0.0373(15) 0.0261(14) 0.0083(11) 0.0032(12) 0.0017(13) O7 0.0780(18) 0.0303(14) 0.0263(13) 0.0056(10) 0.0041(13) 0.0004(12) O8 0.097(2) 0.0311(15) 0.0447(16) 0.0070(12) 0.0006(15) -0.0017(14) O9 0.101(2) 0.0442(17) 0.0300(15) 0.0096(12) -0.0069(14) 0.0003(15) O10 0.0757(18) 0.0440(16) 0.0242(13) 0.0014(11) -0.0103(12) 0.0036(13) O11 0.096(2) 0.0321(15) 0.0291(13) -0.0060(11) 0.0025(13) 0.0053(13) O12 0.0674(17) 0.0457(15) 0.0231(13) -0.0036(11) 0.0033(11) 0.0007(12) C1 0.0353(19) 0.031(2) 0.035(2) 0.0081(15) 0.0033(15) 0.0009(15) C2 0.0339(19) 0.035(2) 0.0232(18) -0.0024(14) 0.0006(14) 0.0021(15) C3 0.0344(19) 0.0301(19) 0.0285(18) 0.0024(15) 0.0033(14) 0.0089(15) C4 0.0244(16) 0.0295(18) 0.0236(17) -0.0016(13) 0.0032(13) 0.0033(13) C5 0.0392(19) 0.034(2) 0.0238(17) -0.0037(14) 0.0032(14) -0.0021(16) C6 0.048(2) 0.042(2) 0.044(2) -0.0164(17) 0.0085(18) -0.0045(17) C7 0.0348(18) 0.0304(19) 0.0225(17) -0.0028(14) -0.0013(14) -0.0015(15) C8 0.0273(17) 0.0261(18) 0.0203(16) -0.0015(13) 0.0025(13) -0.0012(13) C9 0.0318(17) 0.0189(16) 0.0273(17) 0.0000(13) 0.0016(14) 0.0014(13) C10 0.0225(16) 0.0266(17) 0.0215(16) -0.0015(13) 0.0018(13) 0.0002(13) C11 0.0194(15) 0.0245(17) 0.0261(17) 0.0014(13) 0.0015(13) 0.0002(13) C12 0.0358(18) 0.0182(16) 0.0308(17) 0.0002(13) 0.0016(14) -0.0003(13) C13 0.0377(18) 0.0259(17) 0.0256(17) -0.0044(13) 0.0025(14) -0.0039(14) C14 0.0308(17) 0.0251(18) 0.0285(17) -0.0001(13) 0.0005(14) 0.0025(14) C15 0.0235(17) 0.0287(18) 0.0256(17) -0.0006(13) 0.0021(13) 0.0024(13) C16 0.0252(17) 0.0292(18) 0.0285(18) 0.0026(14) 0.0017(14) 0.0030(14) C17 0.048(2) 0.034(2) 0.035(2) 0.0050(16) 0.0012(16) 0.0020(17) C18 0.0333(17) 0.0316(19) 0.0248(17) -0.0050(14) -0.0002(14) 0.0037(14) C19 0.0332(18) 0.0244(18) 0.0341(19) -0.0037(14) 0.0019(15) 0.0021(14) N1 0.0483(19) 0.0271(17) 0.0405(18) -0.0090(14) -0.0058(15) 0.0013(14) C20 0.051(2) 0.032(2) 0.044(2) 0.0007(16) -0.0095(18) -0.0008(17) C21 0.062(3) 0.049(2) 0.035(2) -0.0139(17) 0.0113(18) -0.0135(19) N2 0.049(2) 0.050(2) 0.0239(16) -0.0094(14) -0.0061(14) 0.0003(15) OS2 0.101(7) 0.151(9) 0.083(7) -0.015(5) 0.040(7) 0.007(9) OS3 0.115(7) 0.117(7) 0.052(5) -0.020(4) 0.019(7) 0.004(8) _geom_special_details ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_bi63f _database_code_depnum_ccdc_archive 'CCDC 882498' #TrackingRef '- 63F.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H20 N9 O10' _chemical_formula_weight 498.41 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 C2/c _symmetry_space_group_name_Hall '- C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 26.766(6) _cell_length_b 11.962(2) _cell_length_c 7.0676(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.866(7) _cell_angle_gamma 90.00 _cell_volume 2222.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour lilac _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1036 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9097 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'micro-focus sealed tube' _diffrn_radiation_monochromator 'doubly curved silicon crystal' _diffrn_measurement_device_type 'Bruker SMART X2S' _diffrn_measurement_method '\w scans' _diffrn_standards_decay_% ? _diffrn_reflns_number 10169 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.74 _diffrn_reflns_theta_max 25.06 _reflns_number_total 1949 _reflns_number_gt 1334 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _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^)+(0.1687P)^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 SHELXL _refine_ls_extinction_coef 0.006(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1949 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1170 _refine_ls_R_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.2837 _refine_ls_wR_factor_gt 0.2623 _refine_ls_goodness_of_fit_ref 1.222 _refine_ls_restrained_S_all 1.222 _refine_ls_shift/su_max 0.007 _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 O4 O 0.17085(10) 0.9815(2) 0.0870(4) 0.0516(9) Uani 1 1 d . . . N5 N 0.23894(11) 0.8836(3) 0.2442(4) 0.0416(9) Uani 1 1 d . . . H5 H 0.2227 0.8221 0.2141 0.050 Uiso 1 1 calc R . . N4 N 0.23947(11) 1.0768(2) 0.2423(4) 0.0407(9) Uani 1 1 d . . . H4 H 0.2240 1.1391 0.2109 0.049 Uiso 1 1 calc R . . O3 O 0.30561(10) 0.7804(2) 0.3860(4) 0.0517(9) Uani 1 1 d . . . O2 O 0.30730(10) 1.1775(2) 0.3856(4) 0.0522(9) Uani 1 1 d . . . C6 C 0.28782(14) 0.8744(3) 0.3465(5) 0.0388(9) Uani 1 1 d . . . N3 N 0.36261(13) 0.9915(3) 0.4916(5) 0.0472(10) Uani 1 1 d . . . C5 C 0.28828(13) 1.0826(3) 0.3458(5) 0.0367(9) Uani 1 1 d . . . C4 C 0.31425(14) 0.9791(3) 0.4005(5) 0.0366(9) Uani 1 1 d . . . C3 C 0.21334(13) 0.9810(3) 0.1851(5) 0.0361(9) Uani 1 1 d . . . O1 O 0.38831(11) 0.9064(3) 0.5455(5) 0.0653(10) Uani 1 1 d . . . N2 N 0.5000 1.3029(4) 0.7500 0.0665(17) Uani 1 2 d S . . N1 N 0.41082(17) 1.2285(4) 0.4940(6) 0.0785(14) Uani 1 1 d . . . C2 C 0.40828(16) 1.2952(4) 0.6719(7) 0.0676(15) Uani 1 1 d . . . H2A H 0.3776 1.3402 0.6506 0.081 Uiso 1 1 calc R . . H2B H 0.4070 1.2450 0.7786 0.081 Uiso 1 1 calc R . . C1 C 0.45358(15) 1.3691(4) 0.7205(7) 0.0602(13) Uani 1 1 d . . . H1A H 0.4539 1.4221 0.6168 0.072 Uiso 1 1 calc R . . H1B H 0.4519 1.4110 0.8367 0.072 Uiso 1 1 calc R . . OW1 O 0.38979(14) 0.3341(3) 0.1323(5) 0.0628(11) Uani 1 1 d . . . C7 C 0.5022(3) 1.2531(10) 0.9680(13) 0.151(3) Uani 1 1 d . . . H7A H 0.5067 1.3134 1.0614 0.182 Uiso 1 1 calc R . . H7B H 0.4708 1.2142 0.9755 0.182 Uiso 1 1 calc R . . C8 C 0.4546(3) 1.1759(9) 0.4926(14) 0.148(3) Uani 1 1 d . . . H8 H 0.4574 1.0998 0.4695 0.178 Uiso 1 1 calc R . . H102 H 0.3796(19) 0.292(4) 0.100(7) 0.040(16) 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 O4 0.0361(17) 0.0444(17) 0.0659(19) 0.0005(13) -0.0114(13) -0.0021(12) N5 0.0368(18) 0.0315(17) 0.052(2) -0.0004(13) -0.0029(14) -0.0064(13) N4 0.0359(18) 0.0310(17) 0.052(2) 0.0002(13) 0.0001(14) 0.0012(13) O3 0.0450(17) 0.0311(15) 0.069(2) 0.0020(12) -0.0157(13) 0.0032(11) O2 0.0365(16) 0.0336(16) 0.077(2) 0.0048(13) -0.0128(13) -0.0063(12) C6 0.037(2) 0.041(2) 0.036(2) 0.0010(16) 0.0004(15) -0.0016(16) N3 0.0377(19) 0.047(2) 0.052(2) 0.0030(14) -0.0040(15) 0.0045(15) C5 0.0294(19) 0.038(2) 0.040(2) 0.0019(15) -0.0006(15) -0.0030(15) C4 0.034(2) 0.034(2) 0.039(2) 0.0002(15) 0.0008(15) -0.0040(15) C3 0.027(2) 0.035(2) 0.044(2) -0.0006(15) 0.0012(16) -0.0009(14) O1 0.0478(18) 0.054(2) 0.084(2) 0.0070(15) -0.0143(15) 0.0041(14) N2 0.037(3) 0.054(3) 0.095(4) 0.000 -0.024(3) 0.000 N1 0.041(2) 0.118(4) 0.069(3) 0.004(2) -0.0065(18) -0.028(2) C2 0.032(2) 0.095(4) 0.072(3) 0.020(3) -0.001(2) 0.004(2) C1 0.045(3) 0.063(3) 0.067(3) 0.005(2) -0.006(2) 0.009(2) OW1 0.059(2) 0.059(2) 0.065(2) -0.0127(18) -0.0027(16) -0.0100(18) C7 0.093(6) 0.224(9) 0.127(7) 0.024(6) -0.005(5) 0.036(6) C8 0.107(7) 0.168(8) 0.157(8) -0.008(6) -0.007(5) -0.049(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 O4 C3 1.215(5) . ? N5 C6 1.375(5) . ? N5 C3 1.376(4) . ? N4 C3 1.364(5) . ? N4 C5 1.373(5) . ? O3 C6 1.232(4) . ? O2 C5 1.255(4) . ? C6 C4 1.454(5) . ? N3 O1 1.247(4) . ? N3 C4 1.341(5) . ? C5 C4 1.437(5) . ? N2 C1 1.455(5) 2_656 ? N2 C1 1.455(5) . ? N2 C7 1.643(10) 2_656 ? N2 C7 1.643(10) . ? N1 C8 1.332(10) . ? N1 C2 1.502(7) . ? C2 C1 1.488(6) . ? C7 C8 1.466(11) 2_656 ? C8 C7 1.466(11) 2_656 ? 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 N5 C3 126.7(3) . . ? C3 N4 C5 125.7(3) . . ? O3 C6 N5 118.8(3) . . ? O3 C6 C4 125.3(3) . . ? N5 C6 C4 115.9(3) . . ? O1 N3 C4 118.9(3) . . ? O2 C5 N4 118.0(3) . . ? O2 C5 C4 124.4(3) . . ? N4 C5 C4 117.6(3) . . ? N3 C4 C5 114.1(3) . . ? N3 C4 C6 126.9(3) . . ? C5 C4 C6 119.0(3) . . ? O4 C3 N4 122.5(3) . . ? O4 C3 N5 122.5(3) . . ? N4 C3 N5 115.1(3) . . ? C1 N2 C1 114.0(5) 2_656 . ? C1 N2 C7 102.1(4) 2_656 2_656 ? C1 N2 C7 100.6(4) . 2_656 ? C1 N2 C7 100.6(4) 2_656 . ? C1 N2 C7 102.1(4) . . ? C7 N2 C7 137.5(9) 2_656 . ? C8 N1 C2 115.9(5) . . ? C1 C2 N1 110.2(4) . . ? N2 C1 C2 110.3(4) . . ? C8 C7 N2 107.1(7) 2_656 . ? N1 C8 C7 111.4(9) . 2_656 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.686 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.090