Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_section_title ; Stereoselective NaN3-Catalized Halonitroaldol-Type Reaction of Azetidine-2,3-diones in Aqueous Media ; _publ_contact_author_name 'Benito Alcaide' _publ_contact_author_email ALCAIDEB@QUIM.UCM.ES loop_ _publ_author_name B.Alcaide P.Almendros A.Luna M.R.Torres # Attachment 'Comp_6.CIF' data_1 _database_code_depnum_ccdc_archive 'CCDC 664893' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H13 N O5' _chemical_formula_weight 251.23 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.5660(5) _cell_length_b 7.3847(6) _cell_length_c 24.1727(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1172.08(16) _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 thin _exptl_crystal_colour colorless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.112 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9712 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2296 _reflns_number_gt 1605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0331P)^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 0.00 _refine_ls_number_reflns 2296 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0717 _refine_ls_wR_factor_gt 0.0636 _refine_ls_goodness_of_fit_ref 0.972 _refine_ls_restrained_S_all 0.972 _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 C2 C 0.3520(3) 0.3116(3) 0.14871(7) 0.0373(5) Uani 1 1 d . . . C3 C 0.4246(3) 0.4712(3) 0.18292(8) 0.0440(5) Uani 1 1 d . . . C4 C 0.2503(3) 0.4961(3) 0.22387(8) 0.0535(6) Uani 1 1 d . . . H4A H 0.2992 0.5516 0.2577 0.064 Uiso 1 1 calc R . . H4B H 0.1450 0.5725 0.2081 0.064 Uiso 1 1 calc R . . C6 C 0.1887(3) 0.2188(3) 0.18554(7) 0.0397(4) Uani 1 1 d . . . C7 C 0.0360(3) 0.2749(3) 0.14012(8) 0.0400(5) Uani 1 1 d . . . C8 C 0.1863(3) 0.4259(2) 0.05513(7) 0.0386(4) Uani 1 1 d . . . C9 C 0.0116(3) 0.4145(3) 0.02238(8) 0.0457(5) Uani 1 1 d . . . H9 H -0.1044 0.3566 0.0356 0.055 Uiso 1 1 calc R . . C10 C 0.0129(3) 0.4896(3) -0.02962(8) 0.0506(5) Uani 1 1 d . . . H10 H -0.1039 0.4835 -0.0513 0.061 Uiso 1 1 calc R . . C11 C 0.1846(4) 0.5738(3) -0.05020(7) 0.0474(5) Uani 1 1 d . . . C12 C 0.3580(3) 0.5836(3) -0.01828(8) 0.0510(5) Uani 1 1 d . . . H12 H 0.4747 0.6389 -0.0321 0.061 Uiso 1 1 calc R . . C13 C 0.3574(3) 0.5098(3) 0.03486(7) 0.0479(5) Uani 1 1 d . . . H13 H 0.4737 0.5175 0.0567 0.057 Uiso 1 1 calc R . . C15 C 0.3421(4) 0.7190(3) -0.12733(8) 0.0700(7) Uani 1 1 d . . . H15A H 0.3834 0.8252 -0.1074 0.105 Uiso 1 1 calc R . . H15B H 0.3128 0.7507 -0.1650 0.105 Uiso 1 1 calc R . . H15C H 0.4499 0.6312 -0.1265 0.105 Uiso 1 1 calc R . . N1 N 0.1861(2) 0.3471(2) 0.10880(6) 0.0393(4) Uani 1 1 d . . . O3 O 0.5992(2) 0.4149(2) 0.21358(6) 0.0535(4) Uani 1 1 d . . . O5 O 0.1727(2) 0.3183(2) 0.23470(5) 0.0533(4) Uani 1 1 d . . . O6 O 0.1896(2) 0.03722(19) 0.19576(6) 0.0551(4) Uani 1 1 d . . . O7 O -0.14815(19) 0.2679(2) 0.13384(6) 0.0530(4) Uani 1 1 d . . . O14 O 0.1661(3) 0.6451(2) -0.10249(5) 0.0657(4) Uani 1 1 d . . . H3 H 0.687(3) 0.365(3) 0.1893(8) 0.078(8) Uiso 1 1 d . . . H6 H 0.279(3) 0.008(3) 0.2221(8) 0.073(8) Uiso 1 1 d . . . H2 H 0.456(3) 0.240(2) 0.1338(6) 0.029(5) Uiso 1 1 d . . . H3A H 0.449(3) 0.583(2) 0.1605(7) 0.046(5) 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 C2 0.0302(10) 0.0495(12) 0.0321(10) -0.0044(9) -0.0015(9) -0.0004(10) C3 0.0397(11) 0.0475(13) 0.0448(12) -0.0019(11) -0.0052(9) -0.0051(9) C4 0.0532(13) 0.0548(14) 0.0526(13) -0.0149(12) -0.0011(10) 0.0037(11) C6 0.0402(10) 0.0480(12) 0.0307(10) -0.0012(9) -0.0005(9) -0.0033(10) C7 0.0354(11) 0.0466(12) 0.0380(11) -0.0035(9) 0.0000(9) -0.0013(10) C8 0.0451(11) 0.0408(11) 0.0300(10) -0.0010(8) -0.0017(9) -0.0013(10) C9 0.0446(12) 0.0525(13) 0.0401(12) -0.0013(10) -0.0024(9) -0.0049(10) C10 0.0538(12) 0.0574(13) 0.0406(12) -0.0033(11) -0.0105(10) 0.0041(12) C11 0.0639(13) 0.0460(12) 0.0322(11) 0.0006(9) 0.0013(11) 0.0068(11) C12 0.0571(13) 0.0529(13) 0.0430(12) 0.0014(10) 0.0065(10) -0.0058(11) C13 0.0456(12) 0.0593(13) 0.0387(11) 0.0024(10) -0.0032(10) -0.0064(11) C15 0.0963(18) 0.0694(16) 0.0442(13) 0.0071(11) 0.0139(14) 0.0014(16) N1 0.0329(8) 0.0535(10) 0.0316(8) 0.0045(7) -0.0037(7) -0.0055(8) O3 0.0425(9) 0.0714(11) 0.0467(9) -0.0156(8) -0.0110(7) 0.0000(7) O5 0.0533(8) 0.0699(10) 0.0368(7) -0.0073(7) 0.0063(7) -0.0074(8) O6 0.0608(9) 0.0521(9) 0.0524(9) 0.0125(7) -0.0188(8) -0.0106(8) O7 0.0320(8) 0.0779(10) 0.0490(8) -0.0005(7) -0.0030(7) -0.0032(8) O14 0.0836(11) 0.0737(10) 0.0399(8) 0.0131(8) 0.0029(9) 0.0056(10) _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 C2 N1 1.479(2) . ? C2 C3 1.516(3) . ? C2 C6 1.553(3) . ? C2 H2 0.936(16) . ? C3 O3 1.427(2) . ? C3 C4 1.524(3) . ? C3 H3A 0.999(17) . ? C4 O5 1.433(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 O6 1.364(2) . ? C6 O5 1.401(2) . ? C6 C7 1.543(2) . ? C7 O7 1.220(2) . ? C7 N1 1.352(2) . ? C8 C13 1.373(3) . ? C8 C9 1.396(2) . ? C8 N1 1.422(2) . ? C9 C10 1.374(2) . ? C9 H9 0.9300 . ? C10 C11 1.381(3) . ? C10 H10 0.9300 . ? C11 O14 1.374(2) . ? C11 C12 1.377(3) . ? C12 C13 1.395(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C15 O14 1.412(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? O3 H3 0.90(2) . ? O6 H6 0.89(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 N1 C2 C3 116.74(16) . . ? N1 C2 C6 86.75(13) . . ? C3 C2 C6 104.33(15) . . ? N1 C2 H2 112.7(10) . . ? C3 C2 H2 114.7(9) . . ? C6 C2 H2 118.5(10) . . ? O3 C3 C2 108.04(16) . . ? O3 C3 C4 107.51(16) . . ? C2 C3 C4 102.23(15) . . ? O3 C3 H3A 113.2(10) . . ? C2 C3 H3A 113.3(10) . . ? C4 C3 H3A 111.9(10) . . ? O5 C4 C3 105.96(17) . . ? O5 C4 H4A 110.5 . . ? C3 C4 H4A 110.5 . . ? O5 C4 H4B 110.5 . . ? C3 C4 H4B 110.5 . . ? H4A C4 H4B 108.7 . . ? O6 C6 O5 111.23(15) . . ? O6 C6 C7 113.30(15) . . ? O5 C6 C7 114.47(16) . . ? O6 C6 C2 122.33(16) . . ? O5 C6 C2 107.86(15) . . ? C7 C6 C2 85.55(13) . . ? O7 C7 N1 132.02(19) . . ? O7 C7 C6 136.15(18) . . ? N1 C7 C6 91.76(14) . . ? C13 C8 C9 119.81(16) . . ? C13 C8 N1 120.72(17) . . ? C9 C8 N1 119.46(17) . . ? C8 C9 C10 119.29(18) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C11 C10 C9 121.12(18) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? O14 C11 C10 115.60(19) . . ? O14 C11 C12 124.6(2) . . ? C10 C11 C12 119.78(17) . . ? C11 C12 C13 119.55(19) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C8 C13 C12 120.45(18) . . ? C8 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? O14 C15 H15A 109.5 . . ? O14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 N1 C8 132.29(15) . . ? C7 N1 C2 95.84(13) . . ? C8 N1 C2 131.84(15) . . ? C3 O3 H3 107.3(13) . . ? C6 O5 C4 107.39(14) . . ? C6 O6 H6 111.5(16) . . ? C11 O14 C15 117.82(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 O3 -173.14(15) . . . . ? C6 C2 C3 O3 93.23(17) . . . . ? N1 C2 C3 C4 73.6(2) . . . . ? C6 C2 C3 C4 -20.00(19) . . . . ? O3 C3 C4 O5 -80.04(18) . . . . ? C2 C3 C4 O5 33.58(19) . . . . ? N1 C2 C6 O6 112.72(17) . . . . ? C3 C2 C6 O6 -130.50(17) . . . . ? N1 C2 C6 O5 -116.43(14) . . . . ? C3 C2 C6 O5 0.36(19) . . . . ? N1 C2 C6 C7 -2.13(13) . . . . ? C3 C2 C6 C7 114.65(15) . . . . ? O6 C6 C7 O7 61.9(3) . . . . ? O5 C6 C7 O7 -67.1(3) . . . . ? C2 C6 C7 O7 -174.7(2) . . . . ? O6 C6 C7 N1 -121.07(17) . . . . ? O5 C6 C7 N1 109.94(16) . . . . ? C2 C6 C7 N1 2.33(14) . . . . ? C13 C8 C9 C10 -0.8(3) . . . . ? N1 C8 C9 C10 -179.49(17) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C9 C10 C11 O14 -179.41(18) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? O14 C11 C12 C13 178.51(18) . . . . ? C10 C11 C12 C13 -0.7(3) . . . . ? C9 C8 C13 C12 -0.1(3) . . . . ? N1 C8 C13 C12 178.65(17) . . . . ? C11 C12 C13 C8 0.8(3) . . . . ? O7 C7 N1 C8 -6.7(4) . . . . ? C6 C7 N1 C8 176.05(19) . . . . ? O7 C7 N1 C2 174.8(2) . . . . ? C6 C7 N1 C2 -2.45(15) . . . . ? C13 C8 N1 C7 172.16(19) . . . . ? C9 C8 N1 C7 -9.1(3) . . . . ? C13 C8 N1 C2 -9.8(3) . . . . ? C9 C8 N1 C2 168.89(17) . . . . ? C3 C2 N1 C7 -101.98(18) . . . . ? C6 C2 N1 C7 2.44(14) . . . . ? C3 C2 N1 C8 79.5(2) . . . . ? C6 C2 N1 C8 -176.08(19) . . . . ? O6 C6 O5 C4 157.99(16) . . . . ? C7 C6 O5 C4 -72.0(2) . . . . ? C2 C6 O5 C4 21.3(2) . . . . ? C3 C4 O5 C6 -34.9(2) . . . . ? C10 C11 O14 C15 -174.70(19) . . . . ? C12 C11 O14 C15 6.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.138 _refine_diff_density_min -0.120 _refine_diff_density_rms 0.031 # Attachment 'Comp_7.CIF' data_2 _database_code_depnum_ccdc_archive 'CCDC 664894' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 N2 O7' _chemical_formula_weight 350.32 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) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.0409(11) _cell_length_b 6.1566(6) _cell_length_c 12.5748(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.669(2) _cell_angle_gamma 90.00 _cell_volume 854.71(15) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.108 _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 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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7135 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_sigmaI/netI 0.0712 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3333 _reflns_number_gt 1873 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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. ; _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^)+(0.0440P)^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 0.00 _refine_ls_number_reflns 3333 _refine_ls_number_parameters 241 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0919 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0864 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _refine_ls_shift/su_max 0.002 _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 C2 C 0.5970(3) 0.6489(5) 0.0712(2) 0.0482(8) Uani 1 1 d . . . C3 C 0.7055(2) 0.7330(5) 0.0098(2) 0.0429(7) Uani 1 1 d . . . C4 C 0.7179(2) 0.9153(5) 0.0921(2) 0.0431(7) Uani 1 1 d . . . C5 C 0.8338(2) 0.8991(7) 0.1590(2) 0.0541(8) Uani 1 1 d . . . C6 C 0.9407(3) 1.0162(9) 0.1145(3) 0.0976(16) Uani 1 1 d . . . H6A H 0.9884 0.9203 0.0703 0.117 Uiso 1 1 calc R . . H6B H 0.9151 1.1404 0.0725 0.117 Uiso 1 1 calc R . . C7 C 0.9300(3) 1.1004(6) 0.2908(2) 0.0623(10) Uani 1 1 d . . . C8 C 0.9059(4) 1.3275(9) 0.3166(5) 0.149(2) Uani 1 1 d . . . H8A H 0.9804 1.3983 0.3360 0.223 Uiso 1 1 calc R . . H8B H 0.8509 1.3348 0.3751 0.223 Uiso 1 1 calc R . . H8C H 0.8706 1.3986 0.2559 0.223 Uiso 1 1 calc R . . C9 C 0.9867(3) 0.9784(10) 0.3796(3) 0.135(2) Uani 1 1 d . . . H9A H 0.9860 0.8261 0.3633 0.202 Uiso 1 1 calc R . . H9B H 0.9421 1.0036 0.4435 0.202 Uiso 1 1 calc R . . H9C H 1.0687 1.0264 0.3896 0.202 Uiso 1 1 calc R . . C10 C 0.7330(3) 0.7071(6) -0.1022(3) 0.0542(8) Uani 1 1 d . . . C11 C 0.5322(2) 0.8883(5) 0.2234(2) 0.0402(7) Uani 1 1 d . . . C12 C 0.5476(2) 1.0885(5) 0.2711(2) 0.0464(7) Uani 1 1 d . . . H12 H 0.6089 1.1802 0.2481 0.056 Uiso 1 1 calc R . . C13 C 0.4728(2) 1.1552(5) 0.3532(2) 0.0497(8) Uani 1 1 d . . . H13 H 0.4853 1.2891 0.3858 0.060 Uiso 1 1 calc R . . C14 C 0.3801(2) 1.0219(6) 0.3858(2) 0.0530(8) Uani 1 1 d . . . C15 C 0.3639(3) 0.8265(6) 0.3361(2) 0.0645(10) Uani 1 1 d . . . H15 H 0.3001 0.7382 0.3567 0.077 Uiso 1 1 calc R . . C16 C 0.4386(3) 0.7562(5) 0.2566(2) 0.0551(8) Uani 1 1 d . . . H16 H 0.4263 0.6209 0.2254 0.066 Uiso 1 1 calc R . . C17 C 0.3184(3) 1.2638(7) 0.5232(3) 0.0865(13) Uani 1 1 d . . . H17A H 0.4001 1.2728 0.5498 0.130 Uiso 1 1 calc R . . H17B H 0.2634 1.2674 0.5817 0.130 Uiso 1 1 calc R . . H17C H 0.3023 1.3845 0.4769 0.130 Uiso 1 1 calc R . . N1 N 0.60987(17) 0.8152(4) 0.14291(17) 0.0400(6) Uani 1 1 d . . . N2 N 0.7966(2) 0.8861(5) -0.1578(2) 0.0593(7) Uani 1 1 d . . . O1 O 0.52786(18) 0.4988(4) 0.06260(15) 0.0661(6) Uani 1 1 d . . . O2 O 0.80222(17) 0.5994(3) -0.02473(15) 0.0574(6) Uani 1 1 d . . . O3 O 0.77764(18) 0.8991(4) -0.25303(17) 0.0760(7) Uani 1 1 d . . . O4 O 0.8644(3) 0.9997(5) -0.10790(18) 0.0964(9) Uani 1 1 d . . . O5 O 0.81765(15) 1.0002(4) 0.25889(14) 0.0624(7) Uani 1 1 d . . . O6 O 1.0064(2) 1.0816(6) 0.20336(19) 0.1179(13) Uani 1 1 d . . . O7 O 0.30300(18) 1.0688(4) 0.46665(16) 0.0759(7) Uani 1 1 d . . . H4 H 0.705(2) 1.070(5) 0.067(2) 0.051(8) Uiso 1 1 d . . . H10 H 0.682(3) 0.617(6) -0.147(2) 0.080(11) Uiso 1 1 d . . . H5 H 0.859(2) 0.744(5) 0.1678(18) 0.043(8) 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 C2 0.0412(17) 0.057(2) 0.0462(19) -0.0029(17) -0.0032(14) -0.0021(16) C3 0.0382(16) 0.0477(18) 0.0429(18) -0.0036(15) 0.0037(14) 0.0029(15) C4 0.0336(15) 0.051(2) 0.0449(17) 0.0012(16) 0.0067(13) -0.0078(14) C5 0.0310(15) 0.071(2) 0.060(2) -0.0126(19) -0.0041(14) -0.0075(17) C6 0.053(2) 0.172(4) 0.068(2) -0.049(3) 0.0132(19) -0.045(3) C7 0.0501(19) 0.086(3) 0.0502(19) -0.0047(19) 0.0041(16) -0.0248(19) C8 0.145(5) 0.086(4) 0.215(6) -0.037(4) -0.009(4) -0.012(3) C9 0.083(3) 0.179(5) 0.141(4) 0.036(4) -0.063(3) -0.028(3) C10 0.0474(19) 0.064(2) 0.052(2) 0.0017(19) 0.0044(17) -0.0012(17) C11 0.0320(14) 0.0513(19) 0.0373(15) -0.0011(15) -0.0008(13) 0.0027(15) C12 0.0363(15) 0.052(2) 0.0510(18) -0.0017(17) 0.0025(14) -0.0077(14) C13 0.0422(17) 0.0506(19) 0.0563(19) -0.0100(16) 0.0001(15) 0.0009(15) C14 0.0400(17) 0.075(3) 0.0438(18) -0.0075(18) 0.0092(15) -0.0044(17) C15 0.058(2) 0.073(3) 0.063(2) -0.014(2) 0.0199(17) -0.0222(18) C16 0.0500(18) 0.058(2) 0.057(2) -0.0136(17) 0.0154(17) -0.0180(16) C17 0.090(3) 0.098(3) 0.072(2) -0.035(2) 0.014(2) 0.000(2) N1 0.0298(12) 0.0488(15) 0.0415(13) -0.0064(12) 0.0024(10) -0.0058(11) N2 0.0530(16) 0.074(2) 0.0510(18) -0.0004(18) 0.0132(14) 0.0106(16) O1 0.0666(14) 0.0677(15) 0.0640(14) -0.0165(13) 0.0091(11) -0.0288(13) O2 0.0511(12) 0.0664(15) 0.0550(12) 0.0011(12) 0.0098(10) 0.0164(11) O3 0.0679(14) 0.110(2) 0.0502(13) 0.0167(15) -0.0015(11) 0.0208(15) O4 0.125(2) 0.102(2) 0.0621(15) -0.0121(15) 0.0151(15) -0.0506(19) O5 0.0371(11) 0.1067(18) 0.0434(12) -0.0059(13) -0.0019(9) -0.0168(12) O6 0.0745(16) 0.202(4) 0.0773(17) -0.048(2) 0.0224(14) -0.078(2) O7 0.0641(14) 0.098(2) 0.0657(14) -0.0237(15) 0.0278(12) -0.0106(14) _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 C2 O1 1.203(3) . ? C2 N1 1.370(4) . ? C2 C3 1.523(4) . ? C3 O2 1.421(3) . ? C3 C10 1.454(4) . ? C3 C4 1.532(4) . ? C4 N1 1.493(3) . ? C4 C5 1.526(4) . ? C4 H4 1.01(3) . ? C5 O5 1.415(3) . ? C5 C6 1.498(4) . ? C5 H5 1.00(3) . ? C6 O6 1.384(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O6 1.399(4) . ? C7 O5 1.438(3) . ? C7 C8 1.460(6) . ? C7 C9 1.478(5) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 O2 1.399(3) . ? C10 N2 1.486(4) . ? C10 H10 0.97(3) . ? C11 C16 1.384(4) . ? C11 C12 1.380(4) . ? C11 N1 1.408(3) . ? C12 C13 1.391(4) . ? C12 H12 0.9300 . ? C13 C14 1.378(4) . ? C13 H13 0.9300 . ? C14 O7 1.365(3) . ? C14 C15 1.367(4) . ? C15 C16 1.372(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 O7 1.405(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? N2 O4 1.197(3) . ? N2 O3 1.216(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 O1 C2 N1 134.0(3) . . ? O1 C2 C3 135.9(3) . . ? N1 C2 C3 90.2(2) . . ? O2 C3 C2 123.8(2) . . ? O2 C3 C10 58.22(17) . . ? C2 C3 C10 128.9(3) . . ? O2 C3 C4 124.7(2) . . ? C2 C3 C4 88.4(2) . . ? C10 C3 C4 135.8(3) . . ? N1 C4 C3 85.4(2) . . ? N1 C4 C5 114.0(2) . . ? C3 C4 C5 113.1(3) . . ? N1 C4 H4 113.9(16) . . ? C3 C4 H4 118.1(15) . . ? C5 C4 H4 110.4(15) . . ? O5 C5 C6 103.2(3) . . ? O5 C5 C4 110.3(2) . . ? C6 C5 C4 115.0(3) . . ? O5 C5 H5 111.1(15) . . ? C6 C5 H5 106.3(15) . . ? C4 C5 H5 110.8(14) . . ? O6 C6 C5 104.3(2) . . ? O6 C6 H6A 110.9 . . ? C5 C6 H6A 110.9 . . ? O6 C6 H6B 110.9 . . ? C5 C6 H6B 110.9 . . ? H6A C6 H6B 108.9 . . ? O6 C7 O5 105.7(2) . . ? O6 C7 C8 111.5(4) . . ? O5 C7 C8 108.3(3) . . ? O6 C7 C9 107.3(3) . . ? O5 C7 C9 110.4(3) . . ? C8 C7 C9 113.3(4) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 N2 114.9(3) . . ? O2 C10 C3 59.70(18) . . ? N2 C10 C3 118.7(3) . . ? O2 C10 H10 116.6(19) . . ? N2 C10 H10 115.0(18) . . ? C3 C10 H10 120.3(18) . . ? C16 C11 C12 118.8(2) . . ? C16 C11 N1 119.5(3) . . ? C12 C11 N1 121.7(3) . . ? C11 C12 C13 121.0(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 119.6(3) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C13 C14 O7 124.6(3) . . ? C13 C14 C15 118.8(3) . . ? O7 C14 C15 116.6(3) . . ? C16 C15 C14 122.3(3) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C11 C16 C15 119.4(3) . . ? C11 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? O7 C17 H17A 109.5 . . ? O7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C2 N1 C11 130.7(2) . . ? C2 N1 C4 96.0(2) . . ? C11 N1 C4 132.2(2) . . ? O4 N2 O3 125.2(3) . . ? O4 N2 C10 118.9(3) . . ? O3 N2 C10 115.8(3) . . ? C10 O2 C3 62.08(18) . . ? C5 O5 C7 108.7(2) . . ? C7 O6 C6 110.1(2) . . ? C14 O7 C17 119.0(3) . . ? 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 O1 C2 C3 O2 -47.1(5) . . . . ? N1 C2 C3 O2 132.3(3) . . . . ? O1 C2 C3 C10 27.0(6) . . . . ? N1 C2 C3 C10 -153.5(3) . . . . ? O1 C2 C3 C4 -178.9(4) . . . . ? N1 C2 C3 C4 0.5(2) . . . . ? O2 C3 C4 N1 -131.6(2) . . . . ? C2 C3 C4 N1 -0.5(2) . . . . ? C10 C3 C4 N1 150.3(3) . . . . ? O2 C3 C4 C5 -17.5(4) . . . . ? C2 C3 C4 C5 113.7(3) . . . . ? C10 C3 C4 C5 -95.6(4) . . . . ? N1 C4 C5 O5 -58.5(4) . . . . ? C3 C4 C5 O5 -153.9(3) . . . . ? N1 C4 C5 C6 -174.6(3) . . . . ? C3 C4 C5 C6 90.0(4) . . . . ? O5 C5 C6 O6 28.4(4) . . . . ? C4 C5 C6 O6 148.5(3) . . . . ? C2 C3 C10 O2 -110.0(3) . . . . ? C4 C3 C10 O2 108.9(4) . . . . ? O2 C3 C10 N2 -103.7(3) . . . . ? C2 C3 C10 N2 146.3(3) . . . . ? C4 C3 C10 N2 5.2(5) . . . . ? C16 C11 C12 C13 1.7(4) . . . . ? N1 C11 C12 C13 -177.7(2) . . . . ? C11 C12 C13 C14 -1.5(4) . . . . ? C12 C13 C14 O7 178.7(3) . . . . ? C12 C13 C14 C15 -0.2(4) . . . . ? C13 C14 C15 C16 1.7(5) . . . . ? O7 C14 C15 C16 -177.2(3) . . . . ? C12 C11 C16 C15 -0.2(4) . . . . ? N1 C11 C16 C15 179.1(3) . . . . ? C14 C15 C16 C11 -1.5(5) . . . . ? O1 C2 N1 C11 -12.1(5) . . . . ? C3 C2 N1 C11 168.4(3) . . . . ? O1 C2 N1 C4 178.9(3) . . . . ? C3 C2 N1 C4 -0.5(2) . . . . ? C16 C11 N1 C2 16.1(4) . . . . ? C12 C11 N1 C2 -164.5(3) . . . . ? C16 C11 N1 C4 -178.8(3) . . . . ? C12 C11 N1 C4 0.6(4) . . . . ? C3 C4 N1 C2 0.5(2) . . . . ? C5 C4 N1 C2 -112.7(3) . . . . ? C3 C4 N1 C11 -168.2(3) . . . . ? C5 C4 N1 C11 78.6(4) . . . . ? O2 C10 N2 O4 -38.0(4) . . . . ? C3 C10 N2 O4 29.6(4) . . . . ? O2 C10 N2 O3 139.5(3) . . . . ? C3 C10 N2 O3 -152.9(3) . . . . ? N2 C10 O2 C3 109.9(3) . . . . ? C2 C3 O2 C10 118.3(3) . . . . ? C4 C3 O2 C10 -126.7(3) . . . . ? C6 C5 O5 C7 -21.9(4) . . . . ? C4 C5 O5 C7 -145.2(3) . . . . ? O6 C7 O5 C5 7.5(4) . . . . ? C8 C7 O5 C5 127.1(4) . . . . ? C9 C7 O5 C5 -108.3(4) . . . . ? O5 C7 O6 C6 11.8(4) . . . . ? C8 C7 O6 C6 -105.7(4) . . . . ? C9 C7 O6 C6 129.6(4) . . . . ? C5 C6 O6 C7 -25.1(5) . . . . ? C13 C14 O7 C17 -1.3(5) . . . . ? C15 C14 O7 C17 177.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.268 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.034