# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Samantha Callear' _publ_contact_author_email S.K.CALLEAR@SOTON.AC.UK _publ_section_title ; Co-crystallisation of organic alpha,omega-dicarboxylic acids with the cyclic amides 2-pyrrolidinone and 2-imidazolidinone. ; loop_ _publ_author_name 'Samantha Callear' 'Michael B. Hursthouse' 'Terence L. Threlfall' # Attachment '1.cif' data_06skc0040p-1 _database_code_depnum_ccdc_archive 'CCDC 717663' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O6' _chemical_formula_weight 288.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.749(3) _cell_length_b 6.541(3) _cell_length_c 9.903(5) _cell_angle_alpha 80.40(2) _cell_angle_beta 78.70(2) _cell_angle_gamma 71.71(3) _cell_volume 344.5(3) _cell_formula_units_Z 1 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1224 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 154 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9824 _exptl_absorpt_correction_T_max 0.9922 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5982 _diffrn_reflns_av_R_equivalents 0.1351 _diffrn_reflns_av_sigmaI/netI 0.1246 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1199 _reflns_number_gt 539 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.1151P)^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_number_reflns 1199 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1812 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.2185 _refine_ls_wR_factor_gt 0.1665 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 C1 C 0.5761(9) 0.6667(8) 0.1187(5) 0.0553(14) Uani 1 1 d . . . C2 C 0.5841(9) 0.5703(8) -0.0094(5) 0.0588(15) Uani 1 1 d . . . H2A H 0.7563 0.4830 -0.0391 0.071 Uiso 1 1 calc R . . H2B H 0.5371 0.6889 -0.0843 0.071 Uiso 1 1 calc R . . O1A O 0.7327(6) 0.7864(6) 0.1005(3) 0.0655(11) Uani 1 1 d . . . H1 H 0.7121 0.8478 0.1718 0.075(18) Uiso 1 1 calc R . . O1B O 0.4461(7) 0.6409(6) 0.2266(4) 0.0651(11) Uani 1 1 d . . . C22 C 0.7731(9) 0.0825(8) 0.3525(5) 0.0512(13) Uani 1 1 d . . . C23 C 0.9746(9) 0.1546(8) 0.2567(5) 0.0566(14) Uani 1 1 d . . . H23A H 0.9168 0.2298 0.1687 0.068 Uiso 1 1 calc R . . H23B H 1.1210 0.0291 0.2358 0.068 Uiso 1 1 calc R . . C24 C 1.0393(9) 0.3098(8) 0.3337(4) 0.0544(14) Uani 1 1 d . . . H24A H 1.2075 0.2457 0.3592 0.065 Uiso 1 1 calc R . . H24B H 1.0326 0.4495 0.2754 0.065 Uiso 1 1 calc R . . C25 C 0.8428(9) 0.3425(7) 0.4636(5) 0.0517(13) Uani 1 1 d . . . H25A H 0.9209 0.3166 0.5479 0.062 Uiso 1 1 calc R . . H25B H 0.7273 0.4910 0.4574 0.062 Uiso 1 1 calc R . . N21 N 0.7144(7) 0.1827(6) 0.4653(4) 0.0514(11) Uani 1 1 d . . . H21 H 0.6057 0.1546 0.5362 0.021(10) Uiso 1 1 calc R . . O22 O 0.6732(6) -0.0510(5) 0.3319(3) 0.0608(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.066(3) 0.059(3) 0.054(3) -0.013(3) -0.013(3) -0.031(3) C2 0.076(4) 0.062(3) 0.050(3) -0.018(2) -0.006(3) -0.033(3) O1A 0.080(2) 0.086(3) 0.051(2) -0.024(2) 0.0011(18) -0.052(2) O1B 0.077(2) 0.083(3) 0.050(2) -0.0216(18) 0.0044(19) -0.046(2) C22 0.059(3) 0.056(3) 0.047(3) -0.014(3) -0.003(2) -0.028(3) C23 0.067(3) 0.061(3) 0.051(3) -0.014(2) -0.003(3) -0.032(3) C24 0.059(3) 0.065(3) 0.052(3) -0.012(2) -0.002(2) -0.039(3) C25 0.059(3) 0.057(3) 0.054(3) -0.012(2) -0.006(2) -0.035(3) N21 0.060(3) 0.058(3) 0.048(2) -0.009(2) 0.000(2) -0.037(2) O22 0.070(2) 0.072(2) 0.058(2) -0.0242(17) -0.0030(17) -0.043(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1B 1.198(6) . ? C1 O1A 1.337(6) . ? C1 C2 1.495(6) . ? C2 C2 1.499(9) 2_665 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O1A H1 0.8400 . ? C22 O22 1.247(5) . ? C22 N21 1.322(6) . ? C22 C23 1.493(7) . ? C23 C24 1.535(6) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.532(6) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.453(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? 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 O1B C1 O1A 122.9(4) . . ? O1B C1 C2 124.7(4) . . ? O1A C1 C2 112.5(5) . . ? C1 C2 C2 113.6(5) . 2_665 ? C1 C2 H2A 108.9 . . ? C2 C2 H2A 108.9 2_665 . ? C1 C2 H2B 108.9 . . ? C2 C2 H2B 108.9 2_665 . ? H2A C2 H2B 107.7 . . ? C1 O1A H1 109.5 . . ? O22 C22 N21 124.3(4) . . ? O22 C22 C23 126.4(4) . . ? N21 C22 C23 109.3(4) . . ? C22 C23 C24 105.5(4) . . ? C22 C23 H23A 110.6 . . ? C24 C23 H23A 110.6 . . ? C22 C23 H23B 110.6 . . ? C24 C23 H23B 110.6 . . ? H23A C23 H23B 108.8 . . ? C25 C24 C23 105.1(3) . . ? C25 C24 H24A 110.7 . . ? C23 C24 H24A 110.7 . . ? C25 C24 H24B 110.7 . . ? C23 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? N21 C25 C24 104.1(3) . . ? N21 C25 H25A 110.9 . . ? C24 C25 H25A 110.9 . . ? N21 C25 H25B 110.9 . . ? C24 C25 H25B 110.9 . . ? H25A C25 H25B 109.0 . . ? C22 N21 C25 115.1(4) . . ? C22 N21 H21 122.5 . . ? C25 N21 H21 122.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1 O22 0.84 1.77 2.603(4) 173.8 1_565 N21 H21 O22 0.88 2.07 2.935(5) 165.8 2_656 _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.242 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.064 # Attachment '10.cif' data_ssg0306 _database_code_depnum_ccdc_archive 'CCDC 717664' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 10 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H12 N2 O7' _chemical_formula_weight 236.19 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 P21/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 5.1062(11) _cell_length_b 18.198(4) _cell_length_c 10.432(2) _cell_angle_alpha 90.00 _cell_angle_beta 97.060(2) _cell_angle_gamma 90.00 _cell_volume 962.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 930 _cell_measurement_theta_min 3.94 _cell_measurement_theta_max 25.79 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details 'Bruker SADABS' # absolute Tmin and Tmax unknown, but SADABS gives ratio as 0.731 _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.6710 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 7832 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 24.79 _reflns_number_total 1961 _reflns_number_gt 1444 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _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^ > 2\s(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^)+(0.0627P)^2^+0.2714P] 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_number_reflns 1961 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.1082 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6361(4) 0.56576(11) 0.1603(2) 0.0190(5) Uani 1 1 d . . . C2 C 0.5051(4) 0.49324(11) 0.1877(2) 0.0198(5) Uani 1 1 d . . . H2 H 0.6266 0.4528 0.1682 0.024 Uiso 1 1 calc R . . C3 C 0.4862(4) 0.49157(11) 0.3338(2) 0.0210(5) Uani 1 1 d . . . H3 H 0.6697 0.4908 0.3800 0.025 Uiso 1 1 calc R . . C4 C 0.3463(4) 0.42246(12) 0.3705(2) 0.0207(5) Uani 1 1 d . . . O1A O 0.8715(3) 0.57577(8) 0.19328(15) 0.0251(4) Uani 1 1 d . . . O1B O 0.4758(3) 0.61499(8) 0.10315(15) 0.0234(4) Uani 1 1 d . . . H1 H 0.5593 0.6540 0.0940 0.048(9) Uiso 1 1 calc R . . O2 O 0.2592(3) 0.48121(8) 0.11204(14) 0.0229(4) Uani 1 1 d . . . H2O H 0.1521 0.5140 0.1281 0.034 Uiso 1 1 calc R . . O3 O 0.3586(3) 0.55493(8) 0.37335(14) 0.0224(4) Uani 1 1 d . . . H3O H 0.1948 0.5506 0.3538 0.034 Uiso 1 1 calc R . . O4A O 0.4812(3) 0.36240(8) 0.35347(15) 0.0233(4) Uani 1 1 d . . . H4 H 0.3971 0.3256 0.3748 0.026(7) Uiso 1 1 calc R . . O4B O 0.1318(3) 0.42434(8) 0.40880(15) 0.0251(4) Uani 1 1 d . . . C22 C 0.1237(4) 0.23674(11) 0.5131(2) 0.0204(5) Uani 1 1 d . . . C24 C -0.1703(4) 0.27754(12) 0.6500(2) 0.0239(5) Uani 1 1 d . . . H24A H -0.3583 0.2920 0.6331 0.029 Uiso 1 1 calc R . . H24B H -0.0870 0.3029 0.7286 0.029 Uiso 1 1 calc R . . C25 C -0.1388(4) 0.19345(12) 0.6615(2) 0.0232(5) Uani 1 1 d . . . H25A H -0.0980 0.1780 0.7528 0.028 Uiso 1 1 calc R . . H25B H -0.2999 0.1677 0.6223 0.028 Uiso 1 1 calc R . . N21 N 0.0843(4) 0.17953(11) 0.58874(18) 0.0250(4) Uani 1 1 d . . . H21 H 0.1793 0.1390 0.5942 0.081(12) Uiso 1 1 calc R . . N23 N -0.0299(4) 0.29248(10) 0.53861(19) 0.0263(5) Uani 1 1 d . . . H23 H -0.0453 0.3336 0.4938 0.044(8) Uiso 1 1 calc R . . O22 O 0.2864(3) 0.23810(8) 0.43048(15) 0.0232(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0187(10) 0.0220(11) 0.0177(11) -0.0009(8) 0.0079(8) 0.0016(8) C2 0.0165(10) 0.0222(11) 0.0213(11) -0.0004(8) 0.0047(8) 0.0002(8) C3 0.0216(11) 0.0218(11) 0.0203(11) 0.0004(9) 0.0058(8) 0.0006(8) C4 0.0214(10) 0.0236(11) 0.0178(11) 0.0002(9) 0.0050(8) 0.0009(9) O1A 0.0196(8) 0.0267(8) 0.0298(9) 0.0015(7) 0.0057(6) -0.0013(6) O1B 0.0216(8) 0.0221(8) 0.0274(9) 0.0042(7) 0.0064(6) 0.0001(6) O2 0.0200(8) 0.0262(8) 0.0229(8) -0.0022(6) 0.0041(6) -0.0014(6) O3 0.0222(8) 0.0237(8) 0.0223(8) -0.0020(6) 0.0067(6) 0.0005(6) O4A 0.0243(8) 0.0210(8) 0.0264(9) 0.0018(7) 0.0106(6) -0.0005(6) O4B 0.0215(8) 0.0251(8) 0.0306(9) 0.0026(7) 0.0104(6) 0.0006(6) C22 0.0188(10) 0.0227(11) 0.0201(11) 0.0006(9) 0.0048(9) -0.0001(8) C24 0.0229(11) 0.0269(12) 0.0233(12) 0.0003(9) 0.0087(9) 0.0002(9) C25 0.0221(11) 0.0251(11) 0.0237(12) 0.0012(9) 0.0080(9) -0.0002(9) N21 0.0253(10) 0.0248(10) 0.0274(11) 0.0045(8) 0.0130(8) 0.0025(8) N23 0.0298(10) 0.0237(10) 0.0283(11) 0.0060(8) 0.0145(8) 0.0053(8) O22 0.0237(8) 0.0233(8) 0.0244(8) 0.0006(6) 0.0096(6) -0.0002(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1A 1.222(2) . ? C1 O1B 1.307(3) . ? C1 C2 1.522(3) . ? C2 O2 1.416(2) . ? C2 C3 1.539(3) . ? C2 H2 1.0000 . ? C3 O3 1.411(2) . ? C3 C4 1.518(3) . ? C3 H3 1.0000 . ? C4 O4B 1.212(3) . ? C4 O4A 1.316(3) . ? O1B H1 0.8400 . ? O2 H2O 0.8400 . ? O3 H3O 0.8400 . ? O4A H4 0.8400 . ? C22 O22 1.269(2) . ? C22 N23 1.329(3) . ? C22 N21 1.337(3) . ? C24 N23 1.464(3) . ? C24 C25 1.542(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.466(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 124.41(19) . . ? O1A C1 C2 121.06(19) . . ? O1B C1 C2 114.51(17) . . ? O2 C2 C1 114.17(17) . . ? O2 C2 C3 112.93(16) . . ? C1 C2 C3 106.58(17) . . ? O2 C2 H2 107.6 . . ? C1 C2 H2 107.6 . . ? C3 C2 H2 107.6 . . ? O3 C3 C4 110.77(17) . . ? O3 C3 C2 111.18(17) . . ? C4 C3 C2 110.79(17) . . ? O3 C3 H3 108.0 . . ? C4 C3 H3 108.0 . . ? C2 C3 H3 108.0 . . ? O4B C4 O4A 125.3(2) . . ? O4B C4 C3 122.15(19) . . ? O4A C4 C3 112.56(17) . . ? C1 O1B H1 109.5 . . ? C2 O2 H2O 109.5 . . ? C3 O3 H3O 109.5 . . ? C4 O4A H4 109.5 . . ? O22 C22 N23 125.0(2) . . ? O22 C22 N21 125.09(19) . . ? N23 C22 N21 109.93(18) . . ? N23 C24 C25 100.91(17) . . ? N23 C24 H24A 111.6 . . ? C25 C24 H24A 111.6 . . ? N23 C24 H24B 111.6 . . ? C25 C24 H24B 111.6 . . ? H24A C24 H24B 109.4 . . ? N21 C25 C24 102.22(17) . . ? N21 C25 H25A 111.3 . . ? C24 C25 H25A 111.3 . . ? N21 C25 H25B 111.3 . . ? C24 C25 H25B 111.3 . . ? H25A C25 H25B 109.2 . . ? C22 N21 C25 110.72(18) . . ? C22 N21 H21 124.6 . . ? C25 N21 H21 124.6 . . ? C22 N23 C24 112.09(18) . . ? C22 N23 H23 124.0 . . ? C24 N23 H23 124.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4A H4 O22 0.84 1.81 2.636(2) 167.6 . N23 H23 O4B 0.88 2.13 2.924(2) 150.0 . O1B H1 O22 0.84 1.75 2.593(2) 176.1 2_655 O2 H2O O1A 0.84 2.00 2.830(2) 167.4 1_455 O3 H3O O1A 0.84 2.25 2.951(2) 141.2 1_455 N21 H21 O2 0.88 2.23 3.059(2) 157.0 4_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.79 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.366 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.063 # Attachment '11.cif' data_07skc0026p21c _database_code_depnum_ccdc_archive 'CCDC 717665' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 11 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H14 N2 O9' _chemical_formula_weight 318.24 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 P21/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 31.3779(13) _cell_length_b 12.3307(6) _cell_length_c 7.1600(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.968(2) _cell_angle_gamma 90.00 _cell_volume 2766.6(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5433 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.528 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9840 _exptl_absorpt_correction_T_max 0.9973 _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius APEX II CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21095 _diffrn_reflns_av_R_equivalents 0.0902 _diffrn_reflns_av_sigmaI/netI 0.1017 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6257 _reflns_number_gt 3383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0000P)^2^+19.7821P] 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_number_reflns 6257 _refine_ls_number_parameters 405 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2044 _refine_ls_R_factor_gt 0.1184 _refine_ls_wR_factor_ref 0.2395 _refine_ls_wR_factor_gt 0.1928 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 C1 C 0.37286(18) 0.1485(5) -0.0505(8) 0.0209(12) Uani 1 1 d . . . C2 C 0.33654(17) 0.0985(5) 0.0392(8) 0.0215(12) Uani 1 1 d . . . H2 H 0.3366 0.0215 0.0431 0.026 Uiso 1 1 calc R . . C3 C 0.30357(18) 0.1467(5) 0.1160(8) 0.0212(12) Uani 1 1 d . . . H3 H 0.2836 0.0980 0.1653 0.025 Uiso 1 1 calc R . . C4 C 0.29265(16) 0.2637(4) 0.1379(8) 0.0191(12) Uani 1 1 d . . . O1A O 0.39910(12) 0.0807(3) -0.1141(6) 0.0274(10) Uani 1 1 d . . . H1 H 0.4193 0.1143 -0.1606 0.041 Uiso 1 1 calc R . . O1B O 0.37735(12) 0.2504(3) -0.0634(6) 0.0259(9) Uani 1 1 d . . . O4A O 0.31687(12) 0.3397(3) 0.0783(6) 0.0238(9) Uani 1 1 d . . . H4 H 0.3380 0.3120 0.0294 0.036 Uiso 1 1 calc R . . O4B O 0.25954(12) 0.2860(3) 0.2173(6) 0.0242(9) Uani 1 1 d . . . C22 C 0.52104(17) 0.7721(5) 0.2593(8) 0.0217(12) Uani 1 1 d . . . C24 C 0.47721(17) 0.6282(5) 0.3168(9) 0.0257(13) Uani 1 1 d . . . H24A H 0.4520 0.6031 0.2402 0.031 Uiso 1 1 calc R . . H24B H 0.4746 0.6043 0.4477 0.031 Uiso 1 1 calc R . . C25 C 0.51901(18) 0.5865(5) 0.2374(9) 0.0267(14) Uani 1 1 d . . . H25A H 0.5331 0.5321 0.3214 0.032 Uiso 1 1 calc R . . H25B H 0.5137 0.5543 0.1117 0.032 Uiso 1 1 calc R . . N21 N 0.54438(15) 0.6851(4) 0.2288(7) 0.0259(11) Uani 1 1 d . . . H21 H 0.5717 0.6866 0.2061 0.031 Uiso 1 1 calc R . . N23 N 0.48202(15) 0.7453(4) 0.3056(7) 0.0281(12) Uani 1 1 d . . . H23 H 0.4617 0.7923 0.3268 0.034 Uiso 1 1 calc R . . O22 O 0.53327(12) 0.8712(3) 0.2446(6) 0.0270(9) Uani 1 1 d . . . C31 C 0.19862(18) 0.4919(5) 0.3576(8) 0.0232(13) Uani 1 1 d . . . C32 C 0.18514(17) 0.6072(5) 0.3780(8) 0.0224(13) Uani 1 1 d . . . H32 H 0.2035 0.6603 0.3296 0.027 Uiso 1 1 calc R . . C33 C 0.15023(18) 0.6447(5) 0.4563(8) 0.0241(13) Uani 1 1 d . . . H33 H 0.1478 0.7215 0.4524 0.029 Uiso 1 1 calc R . . C34 C 0.11452(18) 0.5912(5) 0.5479(8) 0.0237(13) Uani 1 1 d . . . O31A O 0.17860(12) 0.4129(3) 0.4064(6) 0.0251(9) Uani 1 1 d . . . O31B O 0.23497(12) 0.4850(3) 0.2748(6) 0.0263(9) Uani 1 1 d . . . H31 H 0.2444 0.4214 0.2846 0.039 Uiso 1 1 calc R . . O34A O 0.11208(12) 0.4836(3) 0.5534(6) 0.0264(10) Uani 1 1 d . . . H34 H 0.1337 0.4567 0.5069 0.040 Uiso 1 1 calc R . . O34B O 0.08716(12) 0.6458(3) 0.6184(6) 0.0300(10) Uani 1 1 d . . . C42 C 0.01648(17) 0.4877(5) 1.2179(7) 0.0196(12) Uani 1 1 d . . . C44 C 0.01793(17) 0.6743(5) 1.2353(8) 0.0231(13) Uani 1 1 d . . . H44A H 0.0128 0.7155 1.1177 0.028 Uiso 1 1 calc R . . H44B H 0.0335 0.7208 1.3287 0.028 Uiso 1 1 calc R . . C45 C -0.02449(18) 0.6320(5) 1.3100(8) 0.0237(13) Uani 1 1 d . . . H45A H -0.0260 0.6461 1.4456 0.028 Uiso 1 1 calc R . . H45B H -0.0495 0.6655 1.2425 0.028 Uiso 1 1 calc R . . N41 N -0.02210(15) 0.5152(4) 1.2713(7) 0.0260(11) Uani 1 1 d . . . H41 H -0.0434 0.4695 1.2820 0.031 Uiso 1 1 calc R . . N43 N 0.04128(14) 0.5738(4) 1.2035(7) 0.0208(10) Uani 1 1 d . . . H43 H 0.0684 0.5710 1.1781 0.025 Uiso 1 1 calc R . . O42 O 0.02676(12) 0.3892(3) 1.1871(6) 0.0246(9) Uani 1 1 d . . . C51 C 0.20537(18) 0.5169(5) 0.8443(8) 0.0215(12) Uani 1 1 d . . . C52 C 0.19495(18) 0.4004(5) 0.8719(8) 0.0235(13) Uani 1 1 d . . . H52 H 0.2156 0.3510 0.8295 0.028 Uiso 1 1 calc R . . C53 C 0.16151(18) 0.3543(5) 0.9462(8) 0.0228(13) Uani 1 1 d . . . H53 H 0.1623 0.2773 0.9493 0.027 Uiso 1 1 calc R . . C54 C 0.12295(18) 0.4035(5) 1.0254(8) 0.0224(12) Uani 1 1 d . . . O51A O 0.23826(12) 0.5396(3) 0.7674(6) 0.0257(9) Uani 1 1 d . . . O51B O 0.17967(12) 0.5937(3) 0.8967(6) 0.0228(9) Uani 1 1 d . . . H51 H 0.1579 0.5657 0.9401 0.034 Uiso 1 1 calc R . . O54A O 0.11837(12) 0.5053(3) 1.0334(6) 0.0248(9) Uani 1 1 d . . . O54B O 0.09609(13) 0.3365(3) 1.0819(6) 0.0303(10) Uani 1 1 d . . . H54 H 0.0734 0.3692 1.1045 0.046 Uiso 1 1 calc R . . C61 C 0.38550(17) 0.8446(5) 0.4558(8) 0.0236(13) Uani 1 1 d . . . C62 C 0.34777(18) 0.8989(5) 0.5326(8) 0.0261(13) Uani 1 1 d . . . H62 H 0.3492 0.9759 0.5309 0.031 Uiso 1 1 calc R . . C63 C 0.31242(18) 0.8602(5) 0.6030(8) 0.0226(13) Uani 1 1 d . . . H63 H 0.2926 0.9132 0.6408 0.027 Uiso 1 1 calc R . . C64 C 0.29965(17) 0.7455(5) 0.6308(8) 0.0224(12) Uani 1 1 d . . . O61A O 0.38853(13) 0.7383(3) 0.4492(7) 0.0338(11) Uani 1 1 d . . . H61 H 0.3654 0.7104 0.4786 0.051 Uiso 1 1 calc R . . O61B O 0.41395(14) 0.9014(4) 0.3985(7) 0.0368(11) Uani 1 1 d . . . O64A O 0.32102(13) 0.6660(3) 0.5868(6) 0.0295(10) Uani 1 1 d . . . O64B O 0.26277(12) 0.7367(3) 0.7055(6) 0.0257(9) Uani 1 1 d . . . H64 H 0.2573 0.6709 0.7226 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(3) 0.016(3) 0.025(3) 0.001(2) 0.003(2) 0.001(2) C2 0.020(3) 0.017(3) 0.028(3) 0.002(2) 0.003(2) 0.001(2) C3 0.023(3) 0.017(3) 0.024(3) 0.001(2) 0.004(2) -0.005(2) C4 0.014(3) 0.019(3) 0.024(3) -0.002(2) 0.000(2) -0.002(2) O1A 0.019(2) 0.022(2) 0.042(3) 0.0009(19) 0.0110(19) 0.0022(17) O1B 0.020(2) 0.024(2) 0.034(2) 0.0024(18) 0.0075(17) 0.0025(18) O4A 0.021(2) 0.016(2) 0.035(2) 0.0014(17) 0.0100(18) -0.0032(17) O4B 0.025(2) 0.019(2) 0.029(2) 0.0012(17) 0.0062(17) 0.0022(18) C22 0.017(3) 0.024(3) 0.025(3) 0.003(2) 0.004(2) 0.001(2) C24 0.018(3) 0.024(3) 0.035(3) 0.000(3) 0.004(2) -0.008(2) C25 0.026(3) 0.022(3) 0.033(3) -0.004(3) 0.006(3) -0.007(3) N21 0.021(2) 0.015(3) 0.042(3) -0.003(2) 0.011(2) 0.001(2) N23 0.022(3) 0.022(3) 0.041(3) -0.001(2) 0.013(2) 0.000(2) O22 0.023(2) 0.018(2) 0.041(3) 0.0011(18) 0.0103(18) -0.0006(17) C31 0.021(3) 0.024(3) 0.024(3) -0.001(2) 0.002(2) 0.001(3) C32 0.021(3) 0.017(3) 0.030(3) 0.005(2) 0.004(2) -0.002(2) C33 0.022(3) 0.013(3) 0.038(3) 0.002(2) 0.001(3) 0.000(2) C34 0.019(3) 0.024(3) 0.028(3) -0.001(2) 0.001(2) 0.001(3) O31A 0.024(2) 0.016(2) 0.036(2) -0.0017(18) 0.0113(18) -0.0024(17) O31B 0.019(2) 0.022(2) 0.039(3) -0.0006(19) 0.0118(18) 0.0016(18) O34A 0.021(2) 0.021(2) 0.038(3) 0.0019(18) 0.0118(19) -0.0007(17) O34B 0.021(2) 0.027(2) 0.043(3) -0.002(2) 0.0114(19) 0.0044(19) C42 0.020(3) 0.021(3) 0.018(3) 0.004(2) -0.002(2) -0.001(2) C44 0.022(3) 0.020(3) 0.028(3) 0.002(2) 0.005(2) 0.002(2) C45 0.023(3) 0.025(3) 0.024(3) -0.003(2) 0.004(2) 0.001(3) N41 0.018(2) 0.026(3) 0.036(3) -0.001(2) 0.010(2) -0.004(2) N43 0.015(2) 0.016(2) 0.033(3) 0.000(2) 0.0068(19) 0.0024(19) O42 0.022(2) 0.018(2) 0.035(2) -0.0019(17) 0.0082(18) -0.0005(17) C51 0.019(3) 0.026(3) 0.019(3) -0.001(2) 0.000(2) 0.005(2) C52 0.024(3) 0.017(3) 0.030(3) 0.000(2) 0.010(2) 0.008(2) C53 0.029(3) 0.013(3) 0.027(3) -0.002(2) 0.008(3) 0.007(2) C54 0.021(3) 0.020(3) 0.025(3) -0.002(2) 0.000(2) 0.002(2) O51A 0.017(2) 0.028(2) 0.032(2) 0.0012(19) 0.0097(17) 0.0018(18) O51B 0.021(2) 0.014(2) 0.034(2) 0.0005(17) 0.0095(18) 0.0003(16) O54A 0.021(2) 0.020(2) 0.035(2) -0.0004(17) 0.0087(18) 0.0036(17) O54B 0.021(2) 0.020(2) 0.051(3) 0.002(2) 0.011(2) -0.0002(18) C61 0.017(3) 0.026(3) 0.027(3) 0.002(3) -0.006(2) 0.002(3) C62 0.024(3) 0.021(3) 0.034(3) 0.001(3) 0.012(3) 0.003(3) C63 0.027(3) 0.018(3) 0.023(3) -0.006(2) 0.005(2) 0.009(2) C64 0.015(3) 0.030(3) 0.023(3) 0.002(3) 0.005(2) -0.003(3) O61A 0.025(2) 0.025(2) 0.053(3) -0.004(2) 0.016(2) 0.0020(19) O61B 0.031(2) 0.031(3) 0.051(3) 0.000(2) 0.015(2) -0.008(2) O64A 0.023(2) 0.023(2) 0.044(3) -0.0037(19) 0.013(2) 0.0015(18) O64B 0.020(2) 0.018(2) 0.040(2) -0.0016(19) 0.0081(18) 0.0006(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1B 1.269(7) . ? C1 O1A 1.274(7) . ? C1 C2 1.472(8) . ? C2 C3 1.336(8) . ? C2 H2 0.9500 . ? C3 C4 1.492(8) . ? C3 H3 0.9500 . ? C4 O4B 1.241(6) . ? C4 O4A 1.294(6) . ? O1A H1 0.8400 . ? O4A H4 0.8400 . ? C22 O22 1.287(7) . ? C22 N21 1.324(7) . ? C22 N23 1.327(7) . ? C24 N23 1.454(7) . ? C24 C25 1.545(8) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.456(7) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C31 O31A 1.220(7) . ? C31 O31B 1.315(7) . ? C31 C32 1.492(8) . ? C32 C33 1.339(8) . ? C32 H32 0.9500 . ? C33 C34 1.482(8) . ? C33 H33 0.9500 . ? C34 O34B 1.221(7) . ? C34 O34A 1.329(7) . ? O31B H31 0.8400 . ? O34A H34 0.8400 . ? C42 O42 1.278(7) . ? C42 N43 1.324(7) . ? C42 N41 1.332(7) . ? C44 N43 1.463(7) . ? C44 C45 1.550(7) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 N41 1.468(7) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? N41 H41 0.8800 . ? N43 H43 0.8800 . ? C51 O51A 1.227(7) . ? C51 O51B 1.311(6) . ? C51 C52 1.489(8) . ? C52 C53 1.328(8) . ? C52 H52 0.9500 . ? C53 C54 1.492(8) . ? C53 H53 0.9500 . ? C54 O54B 1.262(7) . ? C54 O54A 1.265(7) . ? O51B H51 0.8400 . ? O54B H54 0.8400 . ? C61 O61B 1.222(7) . ? C61 O61A 1.316(7) . ? C61 C62 1.490(8) . ? C62 C63 1.331(8) . ? C62 H62 0.9500 . ? C63 C64 1.487(8) . ? C63 H63 0.9500 . ? C64 O64A 1.237(7) . ? C64 O64B 1.304(6) . ? O61A H61 0.8400 . ? O64B H64 0.8400 . ? 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 O1B C1 O1A 123.2(5) . . ? O1B C1 C2 122.6(5) . . ? O1A C1 C2 114.2(5) . . ? C3 C2 C1 128.8(5) . . ? C3 C2 H2 115.6 . . ? C1 C2 H2 115.6 . . ? C2 C3 C4 131.3(5) . . ? C2 C3 H3 114.3 . . ? C4 C3 H3 114.3 . . ? O4B C4 O4A 120.7(5) . . ? O4B C4 C3 117.7(5) . . ? O4A C4 C3 121.6(5) . . ? C1 O1A H1 109.5 . . ? C4 O4A H4 109.5 . . ? O22 C22 N21 125.9(5) . . ? O22 C22 N23 122.7(5) . . ? N21 C22 N23 111.4(5) . . ? N23 C24 C25 102.6(4) . . ? N23 C24 H24A 111.3 . . ? C25 C24 H24A 111.3 . . ? N23 C24 H24B 111.3 . . ? C25 C24 H24B 111.3 . . ? H24A C24 H24B 109.2 . . ? N21 C25 C24 102.4(5) . . ? N21 C25 H25A 111.3 . . ? C24 C25 H25A 111.3 . . ? N21 C25 H25B 111.3 . . ? C24 C25 H25B 111.3 . . ? H25A C25 H25B 109.2 . . ? C22 N21 C25 111.2(5) . . ? C22 N21 H21 124.4 . . ? C25 N21 H21 124.4 . . ? C22 N23 C24 111.2(5) . . ? C22 N23 H23 124.4 . . ? C24 N23 H23 124.4 . . ? O31A C31 O31B 123.3(5) . . ? O31A C31 C32 125.4(5) . . ? O31B C31 C32 111.3(5) . . ? C33 C32 C31 127.8(5) . . ? C33 C32 H32 116.1 . . ? C31 C32 H32 116.1 . . ? C32 C33 C34 133.2(5) . . ? C32 C33 H33 113.4 . . ? C34 C33 H33 113.4 . . ? O34B C34 O34A 119.7(5) . . ? O34B C34 C33 120.0(5) . . ? O34A C34 C33 120.3(5) . . ? C31 O31B H31 109.5 . . ? C34 O34A H34 109.5 . . ? O42 C42 N43 126.4(5) . . ? O42 C42 N41 122.2(5) . . ? N43 C42 N41 111.3(5) . . ? N43 C44 C45 102.4(4) . . ? N43 C44 H44A 111.3 . . ? C45 C44 H44A 111.3 . . ? N43 C44 H44B 111.3 . . ? C45 C44 H44B 111.3 . . ? H44A C44 H44B 109.2 . . ? N41 C45 C44 102.2(4) . . ? N41 C45 H45A 111.3 . . ? C44 C45 H45A 111.3 . . ? N41 C45 H45B 111.3 . . ? C44 C45 H45B 111.3 . . ? H45A C45 H45B 109.2 . . ? C42 N41 C45 111.1(5) . . ? C42 N41 H41 124.4 . . ? C45 N41 H41 124.4 . . ? C42 N43 C44 111.5(4) . . ? C42 N43 H43 124.3 . . ? C44 N43 H43 124.3 . . ? O51A C51 O51B 120.5(5) . . ? O51A C51 C52 118.4(5) . . ? O51B C51 C52 121.1(5) . . ? C53 C52 C51 130.5(5) . . ? C53 C52 H52 114.7 . . ? C51 C52 H52 114.7 . . ? C52 C53 C54 130.6(5) . . ? C52 C53 H53 114.7 . . ? C54 C53 H53 114.7 . . ? O54B C54 O54A 123.7(5) . . ? O54B C54 C53 115.1(5) . . ? O54A C54 C53 121.2(5) . . ? C51 O51B H51 109.5 . . ? C54 O54B H54 109.5 . . ? O61B C61 O61A 120.3(5) . . ? O61B C61 C62 118.3(6) . . ? O61A C61 C62 121.4(5) . . ? C63 C62 C61 132.3(6) . . ? C63 C62 H62 113.9 . . ? C61 C62 H62 113.9 . . ? C62 C63 C64 128.9(5) . . ? C62 C63 H63 115.6 . . ? C64 C63 H63 115.6 . . ? O64A C64 O64B 122.9(5) . . ? O64A C64 C63 124.5(5) . . ? O64B C64 C63 112.6(5) . . ? C61 O61A H61 109.5 . . ? C64 O64B H64 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4A H4 O1B 0.84 1.62 2.458(5) 176.1 . N23 H23 O61B 0.88 2.10 2.976(7) 175.7 . N23 H23 O61A 0.88 2.59 3.160(6) 123.6 . O31B H31 O4B 0.84 1.81 2.611(5) 159.4 . O34A H34 O31A 0.84 1.70 2.540(5) 175.1 . N43 H43 O54A 0.88 2.09 2.890(6) 151.3 . O51B H51 O54A 0.84 1.62 2.458(5) 175.4 . O54B H54 O42 0.84 1.63 2.427(5) 158.4 . O61A H61 O64A 0.84 1.72 2.543(6) 167.1 . O64B H64 O51A 0.84 1.76 2.594(6) 171.6 . O1A H1 O22 0.84 1.64 2.436(5) 156.2 3_665 N21 H21 O1B 0.88 2.09 2.892(6) 150.9 3_665 N41 H41 O34B 0.88 2.13 2.984(6) 164.5 3_567 N41 H41 O34A 0.88 2.58 3.149(6) 123.5 3_567 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.435 _refine_diff_density_min -0.412 _refine_diff_density_rms 0.097 # Attachment '2.cif' data_06skc0081p21n _database_code_depnum_ccdc_archive 'CCDC 717666' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 N2 O6' _chemical_formula_weight 286.28 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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.6287(3) _cell_length_b 5.1904(2) _cell_length_c 11.9417(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.971(2) _cell_angle_gamma 90.00 _cell_volume 681.62(4) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1678 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9822 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7393 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 27.47 _reflns_number_total 1553 _reflns_number_gt 1239 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0038P)^2^+0.7980P] 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_number_reflns 1553 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1011 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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 C1 C 0.35614(17) 0.1183(4) 0.02918(16) 0.0230(4) Uani 1 1 d . . . C2 C 0.45781(17) -0.0467(4) 0.01940(16) 0.0234(4) Uani 1 1 d . . . H2 H 0.4611 -0.2228 0.0418 0.028 Uiso 1 1 calc R . . O1A O 0.33254(12) 0.3316(3) -0.01544(13) 0.0281(4) Uani 1 1 d . . . O1B O 0.29561(13) 0.0038(3) 0.09037(12) 0.0276(3) Uani 1 1 d . . . H1 H 0.2344 0.0927 0.0879 0.083(11) Uiso 1 1 calc R . . C22 C 0.52925(17) 0.2932(4) -0.37828(16) 0.0213(4) Uani 1 1 d . . . C23 C 0.54729(17) 0.4965(4) -0.28504(17) 0.0227(4) Uani 1 1 d . . . H23A H 0.5719 0.6622 -0.3115 0.027 Uiso 1 1 calc R . . H23B H 0.6097 0.4435 -0.2102 0.027 Uiso 1 1 calc R . . C24 C 0.42126(17) 0.5179(4) -0.26975(17) 0.0233(4) Uani 1 1 d . . . H24A H 0.4288 0.5433 -0.1855 0.028 Uiso 1 1 calc R . . H24B H 0.3744 0.6631 -0.3167 0.028 Uiso 1 1 calc R . . C25 C 0.36002(17) 0.2592(4) -0.31571(17) 0.0216(4) Uani 1 1 d . . . H25A H 0.3695 0.1363 -0.2499 0.026 Uiso 1 1 calc R . . H25B H 0.2724 0.2824 -0.3595 0.026 Uiso 1 1 calc R . . N21 N 0.42544(14) 0.1715(3) -0.39402(14) 0.0222(4) Uani 1 1 d . . . H21 H 0.3983 0.0488 -0.4469 0.026(6) Uiso 1 1 calc R . . O22 O 0.60204(13) 0.2411(3) -0.43283(13) 0.0292(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0200(9) 0.0276(10) 0.0186(9) -0.0033(8) 0.0023(7) 0.0026(8) C2 0.0233(9) 0.0238(10) 0.0202(9) -0.0012(8) 0.0030(7) -0.0005(8) O1A 0.0262(7) 0.0298(8) 0.0312(8) 0.0020(7) 0.0133(6) 0.0007(6) O1B 0.0267(8) 0.0265(8) 0.0318(8) 0.0041(6) 0.0123(6) 0.0064(6) C22 0.0242(9) 0.0200(9) 0.0208(9) 0.0001(8) 0.0087(8) -0.0002(8) C23 0.0248(10) 0.0216(10) 0.0224(9) -0.0037(8) 0.0086(8) -0.0013(8) C24 0.0279(10) 0.0203(10) 0.0221(9) -0.0012(8) 0.0087(8) 0.0024(8) C25 0.0230(10) 0.0233(10) 0.0203(9) 0.0015(8) 0.0097(7) -0.0003(8) N21 0.0238(8) 0.0218(8) 0.0224(8) -0.0046(7) 0.0092(7) -0.0054(7) O22 0.0289(8) 0.0303(8) 0.0334(8) -0.0102(7) 0.0170(6) -0.0076(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 C1 O1A 1.220(2) . ? C1 O1B 1.310(2) . ? C1 C2 1.495(3) . ? C2 C2 1.307(4) 3_655 ? C2 H2 0.9500 . ? O1B H1 0.8400 . ? C22 O22 1.254(2) . ? C22 N21 1.321(2) . ? C22 C23 1.499(3) . ? C23 C24 1.539(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.535(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.457(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? 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 O1A C1 O1B 124.71(18) . . ? O1A C1 C2 123.84(18) . . ? O1B C1 C2 111.44(17) . . ? C2 C2 C1 121.3(2) 3_655 . ? C2 C2 H2 119.4 3_655 . ? C1 C2 H2 119.4 . . ? C1 O1B H1 109.5 . . ? O22 C22 N21 124.27(18) . . ? O22 C22 C23 125.64(17) . . ? N21 C22 C23 110.08(16) . . ? C22 C23 C24 103.31(15) . . ? C22 C23 H23A 111.1 . . ? C24 C23 H23A 111.1 . . ? C22 C23 H23B 111.1 . . ? C24 C23 H23B 111.1 . . ? H23A C23 H23B 109.1 . . ? C25 C24 C23 104.10(15) . . ? C25 C24 H24A 110.9 . . ? C23 C24 H24A 110.9 . . ? C25 C24 H24B 110.9 . . ? C23 C24 H24B 110.9 . . ? H24A C24 H24B 109.0 . . ? N21 C25 C24 102.97(14) . . ? N21 C25 H25A 111.2 . . ? C24 C25 H25A 111.2 . . ? N21 C25 H25B 111.2 . . ? C24 C25 H25B 111.2 . . ? H25A C25 H25B 109.1 . . ? C22 N21 C25 113.77(16) . . ? C22 N21 H21 123.1 . . ? C25 N21 H21 123.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1B H1 O22 0.84 1.71 2.5476(19) 173.5 4_566 N21 H21 O22 0.88 2.08 2.921(2) 159.9 3_654 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.351 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.054 # Attachment '3.cif' data_06skc0068p21c _database_code_depnum_ccdc_archive 'CCDC 717667' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N4 O6' _chemical_formula_weight 262.23 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 monoclinic _symmetry_space_group_name_H-M P21/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 8.322(4) _cell_length_b 11.203(5) _cell_length_c 11.915(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.79(3) _cell_angle_gamma 90.00 _cell_volume 1100.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 2546 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 28.28 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9865 _exptl_absorpt_correction_T_max 0.9986 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15954 _diffrn_reflns_av_R_equivalents 0.1842 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1934 _reflns_number_gt 1265 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0000P)^2^+9.0267P] 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_number_reflns 1934 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2012 _refine_ls_R_factor_gt 0.1421 _refine_ls_wR_factor_ref 0.2343 _refine_ls_wR_factor_gt 0.2116 _refine_ls_goodness_of_fit_ref 1.243 _refine_ls_restrained_S_all 1.243 _refine_ls_shift/su_max 0.003 _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 C1 C -0.2026(9) -0.1130(7) 0.4687(6) 0.0186(12) Uani 1 1 d . . . C2 C -0.2938(9) -0.1534(7) 0.5644(6) 0.0186(12) Uani 1 1 d . . . O1A O -0.1413(6) -0.1852(5) 0.4105(4) 0.0223(13) Uani 1 1 d . . . O1B O -0.2003(6) 0.0022(5) 0.4570(5) 0.0203(13) Uani 1 1 d . . . H1 H -0.1438 0.0202 0.4062 0.030 Uiso 1 1 calc R . . O2A O -0.2945(7) -0.2683(5) 0.5775(4) 0.0209(13) Uani 1 1 d . . . H2 H -0.3415 -0.2854 0.6335 0.031 Uiso 1 1 calc R . . O2B O -0.3593(6) -0.0840(5) 0.6199(4) 0.0214(13) Uani 1 1 d . . . C22 C -0.0253(10) -0.0242(8) 0.7596(7) 0.024(2) Uani 1 1 d . . . C24 C -0.0981(9) 0.1354(7) 0.8617(6) 0.0200(13) Uani 1 1 d . . . H24A H -0.1758 0.2018 0.8439 0.024 Uiso 1 1 calc R . . H24B H -0.0094 0.1615 0.9204 0.024 Uiso 1 1 calc R . . C25 C -0.1828(10) 0.0220(7) 0.8983(7) 0.0200(13) Uani 1 1 d . . . H25A H -0.1701 0.0139 0.9818 0.024 Uiso 1 1 calc R . . H25B H -0.2995 0.0210 0.8679 0.024 Uiso 1 1 calc R . . N21 N -0.0932(8) -0.0699(6) 0.8465(5) 0.0219(16) Uani 1 1 d . . . H21 H -0.0847 -0.1447 0.8689 0.026 Uiso 1 1 calc R . . N23 N -0.0357(8) 0.0918(6) 0.7603(6) 0.0268(18) Uani 1 1 d . . . H23 H -0.0085 0.1383 0.7064 0.032 Uiso 1 1 calc R . . O22 O 0.0395(7) -0.0884(5) 0.6900(4) 0.0231(14) Uani 1 1 d . . . C32 C -0.5205(9) -0.2108(7) 0.2907(6) 0.0173(19) Uani 1 1 d . . . C34 C -0.6098(10) -0.3733(8) 0.3830(6) 0.024(2) Uani 1 1 d . . . H34A H -0.5251 -0.4121 0.4372 0.028 Uiso 1 1 calc R . . H34B H -0.6995 -0.4304 0.3615 0.028 Uiso 1 1 calc R . . C35 C -0.6704(10) -0.2591(7) 0.4315(7) 0.025(2) Uani 1 1 d . . . H35A H -0.7889 -0.2500 0.4105 0.030 Uiso 1 1 calc R . . H35B H -0.6443 -0.2574 0.5151 0.030 Uiso 1 1 calc R . . N31 N -0.5828(8) -0.1674(6) 0.3796(5) 0.0196(15) Uani 1 1 d . . . H31 H -0.5720 -0.0932 0.4035 0.024 Uiso 1 1 calc R . . N33 N -0.5444(8) -0.3293(6) 0.2851(5) 0.0206(16) Uani 1 1 d . . . H33 H -0.5229 -0.3745 0.2286 0.025 Uiso 1 1 calc R . . O32 O -0.4552(6) -0.1510(5) 0.2210(4) 0.0226(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.013(3) 0.023(3) 0.019(3) -0.007(3) -0.004(2) 0.001(2) C2 0.013(3) 0.023(3) 0.019(3) -0.007(3) -0.004(2) 0.001(2) O1A 0.027(3) 0.019(3) 0.024(3) -0.004(2) 0.013(2) 0.004(3) O1B 0.021(3) 0.014(3) 0.029(3) -0.001(2) 0.016(3) -0.001(2) O2A 0.022(3) 0.018(3) 0.023(3) -0.001(2) 0.004(2) -0.010(2) O2B 0.023(3) 0.022(3) 0.021(3) -0.004(2) 0.011(3) -0.003(3) C22 0.021(5) 0.025(5) 0.025(5) 0.006(4) 0.000(4) 0.000(4) C24 0.021(3) 0.014(3) 0.025(3) -0.004(3) 0.002(3) 0.003(3) C25 0.021(3) 0.014(3) 0.025(3) -0.004(3) 0.002(3) 0.003(3) N21 0.025(4) 0.020(4) 0.022(4) 0.008(3) 0.008(3) 0.007(3) N23 0.042(5) 0.019(4) 0.021(4) 0.004(3) 0.010(3) 0.000(3) O22 0.034(3) 0.020(3) 0.017(3) -0.004(3) 0.009(3) 0.006(3) C32 0.009(4) 0.017(5) 0.024(5) -0.010(4) -0.003(4) 0.004(3) C34 0.018(4) 0.033(5) 0.021(4) -0.001(4) 0.006(4) 0.005(4) C35 0.021(5) 0.029(5) 0.026(5) 0.003(4) 0.005(4) 0.001(4) N31 0.023(4) 0.014(4) 0.022(4) 0.000(3) 0.005(3) 0.001(3) N33 0.024(4) 0.020(4) 0.019(4) -0.007(3) 0.006(3) -0.005(3) O32 0.025(3) 0.021(3) 0.021(3) 0.003(2) 0.000(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1A 1.221(9) . ? C1 O1B 1.298(9) . ? C1 C2 1.522(10) . ? C2 O2B 1.199(9) . ? C2 O2A 1.297(9) . ? O1B H1 0.8400 . ? O2A H2 0.8400 . ? C22 O22 1.272(10) . ? C22 N23 1.303(11) . ? C22 N21 1.346(10) . ? C24 N23 1.462(9) . ? C24 C25 1.544(10) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.457(9) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C32 O32 1.248(9) . ? C32 N31 1.333(9) . ? C32 N33 1.343(10) . ? C34 N33 1.439(10) . ? C34 C35 1.517(11) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 N31 1.446(10) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? N31 H31 0.8800 . ? N33 H33 0.8800 . ? 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 O1A C1 O1B 125.8(7) . . ? O1A C1 C2 121.1(7) . . ? O1B C1 C2 113.1(7) . . ? O2B C2 O2A 124.5(7) . . ? O2B C2 C1 122.1(7) . . ? O2A C2 C1 113.4(7) . . ? C1 O1B H1 109.5 . . ? C2 O2A H2 109.5 . . ? O22 C22 N23 127.1(8) . . ? O22 C22 N21 123.1(8) . . ? N23 C22 N21 109.8(8) . . ? N23 C24 C25 100.7(6) . . ? N23 C24 H24A 111.6 . . ? C25 C24 H24A 111.6 . . ? N23 C24 H24B 111.6 . . ? C25 C24 H24B 111.6 . . ? H24A C24 H24B 109.4 . . ? N21 C25 C24 100.5(6) . . ? N21 C25 H25A 111.7 . . ? C24 C25 H25A 111.7 . . ? N21 C25 H25B 111.7 . . ? C24 C25 H25B 111.7 . . ? H25A C25 H25B 109.4 . . ? C22 N21 C25 110.5(7) . . ? C22 N21 H21 124.8 . . ? C25 N21 H21 124.8 . . ? C22 N23 C24 111.7(7) . . ? C22 N23 H23 124.1 . . ? C24 N23 H23 124.1 . . ? O32 C32 N31 125.8(7) . . ? O32 C32 N33 125.0(7) . . ? N31 C32 N33 109.2(7) . . ? N33 C34 C35 101.7(7) . . ? N33 C34 H34A 111.4 . . ? C35 C34 H34A 111.4 . . ? N33 C34 H34B 111.4 . . ? C35 C34 H34B 111.4 . . ? H34A C34 H34B 109.3 . . ? N31 C35 C34 102.9(6) . . ? N31 C35 H35A 111.2 . . ? C34 C35 H35A 111.2 . . ? N31 C35 H35B 111.2 . . ? C34 C35 H35B 111.2 . . ? H35A C35 H35B 109.1 . . ? C32 N31 C35 110.7(7) . . ? C32 N31 H31 124.6 . . ? C35 N31 H31 124.6 . . ? C32 N33 C34 111.6(6) . . ? C32 N33 H33 124.2 . . ? C34 N33 H33 124.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1B H1 O22 0.84 1.71 2.535(8) 167.3 3_556 N23 H23 O1A 0.88 2.06 2.867(8) 152.1 3_556 O2A H2 O32 0.84 1.66 2.480(8) 164.4 4_556 N21 H21 O1A 0.88 2.04 2.890(8) 162.2 4_556 N31 H31 O2B 0.88 2.07 2.858(8) 147.9 3_456 N33 H33 O2B 0.88 2.06 2.831(8) 146.5 4 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.360 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.093 # Attachment '4.cif' data_ssf1338 _database_code_depnum_ccdc_archive 'CCDC 717668' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N4 O6' _chemical_formula_weight 290.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.5097(15) _cell_length_b 9.529(2) _cell_length_c 13.030(3) _cell_angle_alpha 104.839(3) _cell_angle_beta 91.938(3) _cell_angle_gamma 95.093(3) _cell_volume 657.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 913 _cell_measurement_theta_min 3.61 _cell_measurement_theta_max 29.25 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.122 _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 120(2) _diffrn_radiation_wavelength 0.6905 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 5694 _diffrn_reflns_av_R_equivalents 0.0277 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 26.64 _reflns_number_total 2909 _reflns_number_gt 2337 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _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^)+(0.0846P)^2^+0.3023P] 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_number_reflns 2909 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1486 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0960(3) 0.32238(17) 0.90949(13) 0.0175(3) Uani 1 1 d . . . C2 C -0.0540(3) 0.42133(17) 0.98461(13) 0.0184(4) Uani 1 1 d . . . H2A H -0.0702 0.3868 1.0498 0.022 Uiso 1 1 calc R . . H2B H -0.2197 0.4153 0.9510 0.022 Uiso 1 1 calc R . . O1A O 0.0212(2) 0.18438(13) 0.89571(10) 0.0232(3) Uani 1 1 d . . . H1 H 0.1091 0.1331 0.8529 0.035 Uiso 1 1 calc R . . O1B O 0.2693(2) 0.36534(13) 0.86537(10) 0.0252(3) Uani 1 1 d . . . C22 C 0.5970(3) -0.01663(18) 0.29276(13) 0.0190(3) Uani 1 1 d . . . C24 C 0.2806(3) 0.04334(19) 0.40366(14) 0.0214(4) Uani 1 1 d . . . H24A H 0.1433 0.0823 0.3727 0.026 Uiso 1 1 calc R . . H24B H 0.2789 0.0735 0.4822 0.026 Uiso 1 1 calc R . . C25 C 0.2681(3) -0.12373(19) 0.36197(14) 0.0225(4) Uani 1 1 d . . . H25A H 0.3026 -0.1700 0.4201 0.027 Uiso 1 1 calc R . . H25B H 0.1063 -0.1653 0.3266 0.027 Uiso 1 1 calc R . . N21 N 0.4589(3) -0.14198(17) 0.28625(13) 0.0280(4) Uani 1 1 d . . . H21 H 0.4809 -0.2256 0.2415 0.034 Uiso 1 1 calc R . . N23 N 0.5132(3) 0.09167(16) 0.36767(12) 0.0225(3) Uani 1 1 d . . . H23 H 0.5894 0.1799 0.3916 0.027 Uiso 1 1 calc R . . O22 O 0.7753(2) 0.00200(13) 0.23943(10) 0.0236(3) Uani 1 1 d . . . C31 C 0.2363(3) 0.50094(17) 0.59371(13) 0.0178(3) Uani 1 1 d . . . C32 C 0.4099(3) 0.44165(17) 0.51072(13) 0.0185(3) Uani 1 1 d . . . H32A H 0.3150 0.3904 0.4437 0.022 Uiso 1 1 calc R . . H32B H 0.5009 0.3693 0.5343 0.022 Uiso 1 1 calc R . . O31A O 0.0674(3) 0.40081(14) 0.60433(11) 0.0299(3) Uani 1 1 d . . . H31 H -0.0205 0.4369 0.6538 0.045 Uiso 1 1 calc R . . O31B O 0.2497(2) 0.62819(13) 0.64550(10) 0.0238(3) Uani 1 1 d . . . C42 C -0.7204(3) 0.39826(18) 1.20842(13) 0.0182(3) Uani 1 1 d . . . C44 C -0.5363(3) 0.21210(19) 1.09930(14) 0.0210(4) Uani 1 1 d . . . H44A H -0.3892 0.1899 1.1355 0.025 Uiso 1 1 calc R . . H44B H -0.5274 0.1751 1.0214 0.025 Uiso 1 1 calc R . . C45 C -0.7712(3) 0.14809(18) 1.13788(13) 0.0212(4) Uani 1 1 d . . . H45A H -0.9016 0.1175 1.0802 0.025 Uiso 1 1 calc R . . H45B H -0.7416 0.0640 1.1665 0.025 Uiso 1 1 calc R . . N41 N -0.8318(3) 0.27267(16) 1.22157(11) 0.0211(3) Uani 1 1 d . . . H41 H -0.9275 0.2665 1.2733 0.025 Uiso 1 1 calc R . . N43 N -0.5639(3) 0.36760(15) 1.12953(11) 0.0199(3) Uani 1 1 d . . . H43 H -0.4897 0.4324 1.1007 0.024 Uiso 1 1 calc R . . O42 O -0.7538(2) 0.52470(13) 1.25851(10) 0.0234(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0190(8) 0.0155(8) 0.0178(7) 0.0033(6) 0.0051(6) 0.0020(6) C2 0.0167(8) 0.0168(8) 0.0213(8) 0.0033(6) 0.0074(6) 0.0016(6) O1A 0.0264(7) 0.0147(6) 0.0268(6) 0.0015(5) 0.0127(5) 0.0001(5) O1B 0.0259(7) 0.0172(6) 0.0315(7) 0.0031(5) 0.0169(5) 0.0010(5) C22 0.0198(8) 0.0158(7) 0.0212(8) 0.0040(6) 0.0021(6) 0.0033(6) C24 0.0213(8) 0.0185(8) 0.0238(8) 0.0041(6) 0.0070(6) 0.0006(6) C25 0.0240(9) 0.0192(8) 0.0243(8) 0.0054(7) 0.0054(7) 0.0006(7) N21 0.0280(8) 0.0151(7) 0.0372(9) -0.0006(6) 0.0134(7) 0.0006(6) N23 0.0244(8) 0.0146(7) 0.0262(7) 0.0014(6) 0.0104(6) -0.0012(6) O22 0.0239(6) 0.0194(6) 0.0267(7) 0.0033(5) 0.0102(5) 0.0033(5) C31 0.0171(8) 0.0170(8) 0.0191(8) 0.0038(6) 0.0058(6) 0.0010(6) C32 0.0185(8) 0.0156(7) 0.0201(8) 0.0017(6) 0.0082(6) 0.0013(6) O31A 0.0324(7) 0.0187(6) 0.0339(7) -0.0018(5) 0.0215(6) -0.0051(5) O31B 0.0239(6) 0.0168(6) 0.0275(7) -0.0006(5) 0.0135(5) 0.0003(5) C42 0.0162(8) 0.0199(8) 0.0185(8) 0.0048(6) 0.0050(6) 0.0011(6) C44 0.0212(8) 0.0180(8) 0.0236(8) 0.0037(6) 0.0086(6) 0.0027(6) C45 0.0222(8) 0.0188(8) 0.0222(8) 0.0042(6) 0.0060(6) 0.0015(7) N41 0.0218(7) 0.0191(7) 0.0222(7) 0.0048(6) 0.0104(6) -0.0004(6) N43 0.0215(7) 0.0162(7) 0.0230(7) 0.0054(5) 0.0105(6) 0.0025(5) O42 0.0237(7) 0.0187(6) 0.0267(7) 0.0025(5) 0.0124(5) 0.0021(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 C1 O1B 1.224(2) . ? C1 O1A 1.307(2) . ? C1 C2 1.500(2) . ? C2 C2 1.510(3) 2_567 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O1A H1 0.8400 . ? C22 O22 1.248(2) . ? C22 N21 1.340(2) . ? C22 N23 1.353(2) . ? C24 N23 1.456(2) . ? C24 C25 1.539(2) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.458(2) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C31 O31B 1.2218(19) . ? C31 O31A 1.309(2) . ? C31 C32 1.502(2) . ? C32 C32 1.511(3) 2_666 ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? O31A H31 0.8400 . ? C42 O42 1.248(2) . ? C42 N41 1.349(2) . ? C42 N43 1.355(2) . ? C44 N43 1.456(2) . ? C44 C45 1.536(2) . ? C44 H44A 0.9900 . ? C44 H44B 0.9900 . ? C45 N41 1.463(2) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? N41 H41 0.8800 . ? N43 H43 0.8800 . ? 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 O1B C1 O1A 123.33(14) . . ? O1B C1 C2 124.02(15) . . ? O1A C1 C2 112.65(13) . . ? C1 C2 C2 113.23(17) . 2_567 ? C1 C2 H2A 108.9 . . ? C2 C2 H2A 108.9 2_567 . ? C1 C2 H2B 108.9 . . ? C2 C2 H2B 108.9 2_567 . ? H2A C2 H2B 107.7 . . ? C1 O1A H1 109.5 . . ? O22 C22 N21 127.08(16) . . ? O22 C22 N23 123.64(16) . . ? N21 C22 N23 109.28(15) . . ? N23 C24 C25 102.56(13) . . ? N23 C24 H24A 111.3 . . ? C25 C24 H24A 111.3 . . ? N23 C24 H24B 111.3 . . ? C25 C24 H24B 111.3 . . ? H24A C24 H24B 109.2 . . ? N21 C25 C24 102.31(14) . . ? N21 C25 H25A 111.3 . . ? C24 C25 H25A 111.3 . . ? N21 C25 H25B 111.3 . . ? C24 C25 H25B 111.3 . . ? H25A C25 H25B 109.2 . . ? C22 N21 C25 112.17(14) . . ? C22 N21 H21 123.9 . . ? C25 N21 H21 123.9 . . ? C22 N23 C24 111.24(14) . . ? C22 N23 H23 124.4 . . ? C24 N23 H23 124.4 . . ? O31B C31 O31A 123.53(15) . . ? O31B C31 C32 124.09(15) . . ? O31A C31 C32 112.38(13) . . ? C31 C32 C32 113.14(17) . 2_666 ? C31 C32 H32A 109.0 . . ? C32 C32 H32A 109.0 2_666 . ? C31 C32 H32B 109.0 . . ? C32 C32 H32B 109.0 2_666 . ? H32A C32 H32B 107.8 . . ? C31 O31A H31 109.5 . . ? O42 C42 N41 126.84(15) . . ? O42 C42 N43 123.71(16) . . ? N41 C42 N43 109.44(14) . . ? N43 C44 C45 101.78(13) . . ? N43 C44 H44A 111.4 . . ? C45 C44 H44A 111.4 . . ? N43 C44 H44B 111.4 . . ? C45 C44 H44B 111.4 . . ? H44A C44 H44B 109.3 . . ? N41 C45 C44 101.42(13) . . ? N41 C45 H45A 111.5 . . ? C44 C45 H45A 111.5 . . ? N41 C45 H45B 111.5 . . ? C44 C45 H45B 111.5 . . ? H45A C45 H45B 109.3 . . ? C42 N41 C45 110.55(14) . . ? C42 N41 H41 124.7 . . ? C45 N41 H41 124.7 . . ? C42 N43 C44 110.28(14) . . ? C42 N43 H43 124.9 . . ? C44 N43 H43 124.9 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1 O22 0.84 1.71 2.5293(17) 165.6 2_656 N21 H21 O1B 0.88 2.26 3.047(2) 148.8 2_656 O31A H31 O42 0.84 1.72 2.5418(17) 166.6 2_467 N41 H41 O31B 0.88 2.28 3.0023(19) 139.9 2_467 N23 H23 O31B 0.88 2.13 2.914(2) 147.3 2_666 N43 H43 O1B 0.88 2.12 2.879(2) 144.0 2_567 _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 26.64 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.454 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.058 # Attachment '5.cif' data_07skc0011p21c _database_code_depnum_ccdc_archive 'CCDC 717669' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H22 N4 O6' _chemical_formula_weight 318.34 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 P21/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 7.7814(3) _cell_length_b 22.3584(11) _cell_length_c 9.1957(5) _cell_angle_alpha 90.00 _cell_angle_beta 103.329(3) _cell_angle_gamma 90.00 _cell_volume 1556.77(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3364 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.358 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9859 _exptl_absorpt_correction_T_max 0.9956 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14674 _diffrn_reflns_av_R_equivalents 0.0880 _diffrn_reflns_av_sigmaI/netI 0.0856 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3521 _reflns_number_gt 2194 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^)+(0.0127P)^2^+4.5713P] 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_number_reflns 3521 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1552 _refine_ls_R_factor_gt 0.0934 _refine_ls_wR_factor_ref 0.1880 _refine_ls_wR_factor_gt 0.1574 _refine_ls_goodness_of_fit_ref 1.133 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.003 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9036(5) -0.02891(17) 1.2022(4) 0.0233(8) Uani 1 1 d . . . C2 C 0.8931(5) 0.03736(16) 1.1668(4) 0.0225(8) Uani 1 1 d . . . H2A H 1.0122 0.0520 1.1633 0.027 Uiso 1 1 calc R . . H2B H 0.8556 0.0590 1.2482 0.027 Uiso 1 1 calc R . . C3 C 0.7651(5) 0.05173(16) 1.0190(4) 0.0219(8) Uani 1 1 d . . . H3A H 0.6452 0.0385 1.0238 0.026 Uiso 1 1 calc R . . H3B H 0.8001 0.0290 0.9380 0.026 Uiso 1 1 calc R . . C4 C 0.7598(5) 0.11830(15) 0.9811(4) 0.0191(8) Uani 1 1 d . . . H4A H 0.7294 0.1413 1.0636 0.023 Uiso 1 1 calc R . . H4B H 0.8782 0.1313 0.9713 0.023 Uiso 1 1 calc R . . C5 C 0.6252(5) 0.13175(16) 0.8364(4) 0.0238(9) Uani 1 1 d . . . H5A H 0.6606 0.1107 0.7533 0.029 Uiso 1 1 calc R . . H5B H 0.5089 0.1158 0.8440 0.029 Uiso 1 1 calc R . . C6 C 0.6066(5) 0.19715(17) 0.8003(4) 0.0220(8) Uani 1 1 d . . . O1A O 1.0315(4) -0.04297(12) 1.3160(3) 0.0333(7) Uani 1 1 d . . . H1 H 1.0327 -0.0802 1.3288 0.050 Uiso 1 1 calc R . . O1B O 0.8027(4) -0.06541(11) 1.1299(3) 0.0321(7) Uani 1 1 d . . . O6A O 0.6751(3) 0.23670(11) 0.8838(3) 0.0264(7) Uani 1 1 d . . . O6B O 0.5035(4) 0.20743(12) 0.6662(3) 0.0293(7) Uani 1 1 d . . . H6 H 0.4930 0.2445 0.6517 0.044 Uiso 1 1 calc R . . C22 C 0.4539(5) 0.36287(16) 0.7029(4) 0.0227(8) Uani 1 1 d . . . C24 C 0.5462(6) 0.41567(17) 0.9224(5) 0.0333(10) Uani 1 1 d . . . H24A H 0.6609 0.4325 0.9762 0.040 Uiso 1 1 calc R . . H24B H 0.4736 0.4065 0.9949 0.040 Uiso 1 1 calc R . . C25 C 0.4493(6) 0.45812(17) 0.7992(5) 0.0304(10) Uani 1 1 d . . . H25A H 0.3595 0.4823 0.8333 0.036 Uiso 1 1 calc R . . H25B H 0.5328 0.4852 0.7650 0.036 Uiso 1 1 calc R . . N21 N 0.3677(4) 0.41618(14) 0.6821(4) 0.0276(8) Uani 1 1 d . . . H21 H 0.2760 0.4242 0.6088 0.033 Uiso 1 1 calc R . . N23 N 0.5702(4) 0.36318(14) 0.8357(4) 0.0269(8) Uani 1 1 d . . . H23 H 0.6503 0.3353 0.8664 0.032 Uiso 1 1 calc R . . O22 O 0.4255(3) 0.32078(11) 0.6112(3) 0.0237(6) Uani 1 1 d . . . C32 C 0.0063(5) 0.69651(17) 0.8064(4) 0.0231(8) Uani 1 1 d . . . C34 C -0.0361(5) 0.79529(17) 0.7328(5) 0.0268(9) Uani 1 1 d . . . H34A H 0.0504 0.8112 0.6788 0.032 Uiso 1 1 calc R . . H34B H -0.0913 0.8290 0.7750 0.032 Uiso 1 1 calc R . . C35 C -0.1757(5) 0.75594(16) 0.6307(5) 0.0244(9) Uani 1 1 d . . . H35A H -0.2945 0.7626 0.6494 0.029 Uiso 1 1 calc R . . H35B H -0.1797 0.7635 0.5239 0.029 Uiso 1 1 calc R . . N31 N -0.1118(4) 0.69607(14) 0.6746(4) 0.0280(8) Uani 1 1 d . . . H31 H -0.1461 0.6637 0.6215 0.034 Uiso 1 1 calc R . . N33 N 0.0458(4) 0.75303(13) 0.8483(4) 0.0256(8) Uani 1 1 d . . . H33 H 0.1132 0.7634 0.9352 0.031 Uiso 1 1 calc R . . O32 O 0.0728(4) 0.65166(11) 0.8816(3) 0.0307(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.024(2) 0.021(2) 0.022(2) 0.0011(16) 0.0008(16) 0.0001(16) C2 0.029(2) 0.0144(18) 0.022(2) 0.0029(15) 0.0002(16) 0.0024(15) C3 0.024(2) 0.0173(19) 0.023(2) 0.0021(15) 0.0019(15) -0.0003(15) C4 0.0183(18) 0.0153(18) 0.022(2) -0.0003(14) 0.0011(15) 0.0007(14) C5 0.026(2) 0.0147(18) 0.027(2) -0.0003(16) -0.0015(16) -0.0004(15) C6 0.0199(19) 0.025(2) 0.020(2) 0.0021(16) 0.0021(15) 0.0032(16) O1A 0.0394(17) 0.0165(14) 0.0323(18) 0.0032(12) -0.0157(13) -0.0002(12) O1B 0.0372(16) 0.0168(14) 0.0330(17) 0.0047(12) -0.0108(13) -0.0058(12) O6A 0.0296(15) 0.0166(14) 0.0276(16) -0.0008(11) -0.0044(12) 0.0009(11) O6B 0.0379(17) 0.0176(14) 0.0267(16) 0.0005(12) -0.0042(12) 0.0030(12) C22 0.023(2) 0.0179(19) 0.026(2) 0.0003(16) 0.0019(16) 0.0001(15) C24 0.047(3) 0.022(2) 0.026(2) 0.0016(18) -0.0027(19) 0.0092(19) C25 0.036(2) 0.022(2) 0.030(2) -0.0046(17) 0.0000(18) 0.0033(17) N21 0.0280(18) 0.0217(17) 0.026(2) 0.0007(14) -0.0082(14) 0.0036(14) N23 0.0303(18) 0.0201(17) 0.0248(19) -0.0024(14) -0.0053(14) 0.0094(14) O22 0.0270(14) 0.0177(13) 0.0243(16) 0.0005(11) 0.0016(11) 0.0010(11) C32 0.0232(19) 0.0202(19) 0.025(2) -0.0047(16) 0.0037(16) -0.0007(15) C34 0.029(2) 0.0180(19) 0.029(2) -0.0022(17) -0.0027(17) -0.0008(16) C35 0.024(2) 0.0197(19) 0.028(2) -0.0024(16) 0.0029(16) 0.0008(15) N31 0.0306(18) 0.0183(16) 0.029(2) -0.0079(14) -0.0056(14) -0.0007(14) N33 0.0350(19) 0.0167(16) 0.0205(18) -0.0045(13) -0.0027(14) -0.0032(14) O32 0.0367(16) 0.0167(14) 0.0322(18) -0.0052(12) -0.0057(13) 0.0023(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 C1 O1B 1.218(4) . ? C1 O1A 1.305(4) . ? C1 C2 1.515(5) . ? C2 C3 1.523(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.527(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.521(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.499(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O6A 1.211(4) . ? C6 O6B 1.328(4) . ? O1A H1 0.8400 . ? O6B H6 0.8400 . ? C22 O22 1.249(4) . ? C22 N23 1.342(5) . ? C22 N21 1.360(5) . ? C24 N23 1.454(5) . ? C24 C25 1.536(5) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.458(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C32 O32 1.260(5) . ? C32 N33 1.336(5) . ? C32 N31 1.342(5) . ? C34 N33 1.454(5) . ? C34 C35 1.538(5) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C35 N31 1.452(5) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? N31 H31 0.8800 . ? N33 H33 0.8800 . ? 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 O1B C1 O1A 123.5(3) . . ? O1B C1 C2 122.8(3) . . ? O1A C1 C2 113.6(3) . . ? C1 C2 C3 112.9(3) . . ? C1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 112.8(3) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 111.7(3) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C4 113.5(3) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? O6A C6 O6B 123.1(3) . . ? O6A C6 C5 124.5(3) . . ? O6B C6 C5 112.4(3) . . ? C1 O1A H1 109.5 . . ? C6 O6B H6 109.5 . . ? O22 C22 N23 126.6(3) . . ? O22 C22 N21 124.1(3) . . ? N23 C22 N21 109.3(3) . . ? N23 C24 C25 101.4(3) . . ? N23 C24 H24A 111.5 . . ? C25 C24 H24A 111.5 . . ? N23 C24 H24B 111.5 . . ? C25 C24 H24B 111.5 . . ? H24A C24 H24B 109.3 . . ? N21 C25 C24 101.7(3) . . ? N21 C25 H25A 111.4 . . ? C24 C25 H25A 111.4 . . ? N21 C25 H25B 111.4 . . ? C24 C25 H25B 111.4 . . ? H25A C25 H25B 109.3 . . ? C22 N21 C25 110.1(3) . . ? C22 N21 H21 125.0 . . ? C25 N21 H21 125.0 . . ? C22 N23 C24 111.0(3) . . ? C22 N23 H23 124.5 . . ? C24 N23 H23 124.5 . . ? O32 C32 N33 123.8(3) . . ? O32 C32 N31 126.8(3) . . ? N33 C32 N31 109.3(3) . . ? N33 C34 C35 101.7(3) . . ? N33 C34 H34A 111.4 . . ? C35 C34 H34A 111.4 . . ? N33 C34 H34B 111.4 . . ? C35 C34 H34B 111.4 . . ? H34A C34 H34B 109.3 . . ? N31 C35 C34 102.1(3) . . ? N31 C35 H35A 111.4 . . ? C34 C35 H35A 111.4 . . ? N31 C35 H35B 111.4 . . ? C34 C35 H35B 111.4 . . ? H35A C35 H35B 109.2 . . ? C32 N31 C35 111.3(3) . . ? C32 N31 H31 124.3 . . ? C35 N31 H31 124.3 . . ? C32 N33 C34 111.8(3) . . ? C32 N33 H33 124.1 . . ? C34 N33 H33 124.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6B H6 O22 0.84 1.80 2.628(4) 168.9 . N23 H23 O6A 0.88 2.22 2.948(4) 140.4 . O1A H1 O32 0.84 1.68 2.507(4) 168.2 4_666 N21 H21 O1B 0.88 2.15 2.900(4) 142.6 2_656 N31 H31 O1B 0.88 2.24 3.003(4) 145.4 4_465 N33 H33 O6A 0.88 2.05 2.894(4) 159.1 3_667 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.551 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.083 # Attachment '6.cif' data_06skc0046c2c _database_code_depnum_ccdc_archive 'CCDC 717670' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H22 N6 O7' _chemical_formula_weight 362.36 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 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 16.6403(10) _cell_length_b 14.4382(5) _cell_length_c 7.6872(5) _cell_angle_alpha 90.00 _cell_angle_beta 117.299(2) _cell_angle_gamma 90.00 _cell_volume 1641.20(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1896 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9785 _exptl_absorpt_correction_T_max 0.9880 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10932 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0481 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1868 _reflns_number_gt 1411 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^ > 2\s(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. Non-merohedral twin matrix (1 0 2, 0 -1 0, 0 0 -1) gave BASF parameter 0.1347. ; _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^)+(0.0707P)^2^+0.8687P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1868 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1295 _refine_ls_wR_factor_gt 0.1136 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _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 0.0000 0.25717(19) 0.7500 0.0229(7) Uani 1 2 d S . . H2A H -0.0189 0.2978 0.6340 0.028 Uiso 0.50 1 calc PR . . H2B H 0.0189 0.2978 0.8660 0.028 Uiso 0.50 1 calc PR . . C1 C 0.08090(14) 0.20172(14) 0.7720(3) 0.0227(5) Uani 1 1 d . . . O1A O 0.09902(11) 0.12454(10) 0.8410(3) 0.0314(4) Uani 1 1 d . . . O1B O 0.13161(11) 0.24960(10) 0.7127(3) 0.0286(4) Uani 1 1 d . . . H1 H 0.1792 0.2200 0.7386 0.043 Uiso 1 1 calc R . . C22 C 0.30067(14) 0.09879(14) 0.7980(3) 0.0237(5) Uani 1 1 d . . . C24 C 0.27549(15) -0.05963(14) 0.8004(3) 0.0254(5) Uani 1 1 d . . . H24A H 0.2379 -0.1009 0.6899 0.031 Uiso 1 1 calc R . . H24B H 0.2812 -0.0868 0.9238 0.031 Uiso 1 1 calc R . . C25 C 0.36896(15) -0.04279(14) 0.8104(3) 0.0250(5) Uani 1 1 d . . . H25A H 0.4172 -0.0754 0.9235 0.030 Uiso 1 1 calc R . . H25B H 0.3701 -0.0634 0.6888 0.030 Uiso 1 1 calc R . . N21 N 0.37930(12) 0.05759(12) 0.8336(3) 0.0255(5) Uani 1 1 d . . . H21 H 0.4304 0.0873 0.8667 0.031 Uiso 1 1 calc R . . N23 N 0.23769(12) 0.03373(12) 0.7703(3) 0.0278(5) Uani 1 1 d . . . H23 H 0.1808 0.0461 0.7381 0.033 Uiso 1 1 calc R . . O22 O 0.28866(10) 0.18457(10) 0.7921(3) 0.0301(4) Uani 1 1 d . . . C32 C 0.5000 0.2475(2) 0.7500 0.0219(6) Uani 1 2 d S . . C35 C 0.45317(16) 0.39936(15) 0.7483(4) 0.0297(6) Uani 1 1 d . . . H35A H 0.4532 0.4387 0.8539 0.036 Uiso 1 1 calc R . . H35B H 0.4052 0.4209 0.6206 0.036 Uiso 1 1 calc R . . N31 N 0.44173(13) 0.30174(12) 0.7809(3) 0.0256(5) Uani 1 1 d . . . H31 H 0.4017 0.2808 0.8163 0.031 Uiso 1 1 calc R . . O32 O 0.5000 0.16140(14) 0.7500 0.0256(5) Uani 1 2 d S . . 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 0.0232(16) 0.0175(14) 0.0293(17) 0.000 0.0131(14) 0.000 C1 0.0206(11) 0.0219(11) 0.0259(11) -0.0012(8) 0.0110(9) -0.0009(8) O1A 0.0295(9) 0.0228(8) 0.0492(11) 0.0094(7) 0.0243(8) 0.0058(6) O1B 0.0214(8) 0.0229(8) 0.0464(10) 0.0058(7) 0.0198(8) 0.0027(6) C22 0.0218(11) 0.0226(11) 0.0276(12) 0.0005(8) 0.0121(10) 0.0004(8) C24 0.0256(12) 0.0199(10) 0.0312(12) -0.0008(9) 0.0134(10) -0.0016(8) C25 0.0259(11) 0.0210(11) 0.0286(12) 0.0004(8) 0.0130(10) 0.0029(8) N21 0.0207(10) 0.0203(9) 0.0380(12) -0.0017(7) 0.0155(9) -0.0008(7) N23 0.0189(9) 0.0210(9) 0.0440(12) 0.0005(8) 0.0149(9) -0.0007(7) O22 0.0248(8) 0.0197(8) 0.0500(11) 0.0004(7) 0.0208(8) 0.0006(6) C32 0.0205(15) 0.0220(15) 0.0240(16) 0.000 0.0109(14) 0.000 C35 0.0321(13) 0.0181(10) 0.0399(14) 0.0004(9) 0.0174(11) 0.0031(9) N31 0.0249(10) 0.0221(10) 0.0355(11) 0.0023(8) 0.0188(9) 0.0017(7) O32 0.0252(11) 0.0198(11) 0.0372(13) 0.000 0.0190(11) 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 1.508(3) . ? C2 C1 1.508(3) 2_556 ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C1 O1A 1.211(3) . ? C1 O1B 1.323(3) . ? O1B H1 0.8400 . ? C22 O22 1.252(3) . ? C22 N21 1.346(3) . ? C22 N23 1.350(3) . ? C24 N23 1.460(3) . ? C24 C25 1.541(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.461(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? C32 O32 1.244(3) . ? C32 N31 1.349(2) 2_656 ? C32 N31 1.349(2) . ? C35 N31 1.459(3) . ? C35 C35 1.547(5) 2_656 ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? N31 H31 0.8800 . ? 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 C2 C1 115.8(2) . 2_556 ? C1 C2 H2A 108.3 . . ? C1 C2 H2A 108.3 2_556 . ? C1 C2 H2B 108.3 . . ? C1 C2 H2B 108.3 2_556 . ? H2A C2 H2B 107.4 . . ? O1A C1 O1B 124.16(19) . . ? O1A C1 C2 124.60(19) . . ? O1B C1 C2 111.20(17) . . ? C1 O1B H1 109.5 . . ? O22 C22 N21 124.65(19) . . ? O22 C22 N23 125.69(19) . . ? N21 C22 N23 109.67(18) . . ? N23 C24 C25 102.36(17) . . ? N23 C24 H24A 111.3 . . ? C25 C24 H24A 111.3 . . ? N23 C24 H24B 111.3 . . ? C25 C24 H24B 111.3 . . ? H24A C24 H24B 109.2 . . ? N21 C25 C24 102.84(16) . . ? N21 C25 H25A 111.2 . . ? C24 C25 H25A 111.2 . . ? N21 C25 H25B 111.2 . . ? C24 C25 H25B 111.2 . . ? H25A C25 H25B 109.1 . . ? C22 N21 C25 111.38(17) . . ? C22 N21 H21 124.3 . . ? C25 N21 H21 124.3 . . ? C22 N23 C24 111.75(17) . . ? C22 N23 H23 124.1 . . ? C24 N23 H23 124.1 . . ? O32 C32 N31 125.46(12) . 2_656 ? O32 C32 N31 125.46(12) . . ? N31 C32 N31 109.1(2) 2_656 . ? N31 C35 C35 101.93(12) . 2_656 ? N31 C35 H35A 111.4 . . ? C35 C35 H35A 111.4 2_656 . ? N31 C35 H35B 111.4 . . ? C35 C35 H35B 111.4 2_656 . ? H35A C35 H35B 109.2 . . ? C32 N31 C35 111.68(18) . . ? C32 N31 H31 124.2 . . ? C35 N31 H31 124.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1B H1 O22 0.84 1.75 2.573(2) 166.3 . N21 H21 O32 0.88 2.06 2.807(2) 142.1 . N23 H23 O1A 0.88 2.18 2.914(2) 140.7 . N31 H31 O22 0.88 2.28 3.092(2) 153.9 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.341 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.057 # Attachment '7.cif' data_07skc0005cc _database_code_depnum_ccdc_archive 'CCDC 717671' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 N2 O5' _chemical_formula_weight 218.21 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M Cc 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' _cell_length_a 5.3007(4) _cell_length_b 19.374(2) _cell_length_c 10.0780(9) _cell_angle_alpha 90.00 _cell_angle_beta 94.012(6) _cell_angle_gamma 90.00 _cell_volume 1032.43(16) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 20712 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9713 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8779 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.45 _reflns_number_total 1186 _reflns_number_gt 1005 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^ > 2\s(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. MERG 4 was used as there are no heavy atoms present in the structure (therefore the Flack parameter is meaningless). ; _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^)+(0.0651P)^2^+0.3364P] 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 -10(10) _refine_ls_number_reflns 1186 _refine_ls_number_parameters 138 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1024 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.4059(6) 0.40824(15) 1.0002(3) 0.0252(7) Uani 1 1 d . . . C2 C -0.3910(6) 0.44225(16) 0.8670(3) 0.0240(6) Uani 1 1 d . . . H2A H -0.3661 0.4925 0.8798 0.029 Uiso 1 1 calc R . . H2B H -0.5526 0.4352 0.8133 0.029 Uiso 1 1 calc R . . C3 C -0.1740(6) 0.41304(17) 0.7918(3) 0.0264(6) Uani 1 1 d . . . H3A H -0.0135 0.4190 0.8470 0.032 Uiso 1 1 calc R . . H3B H -0.2013 0.3629 0.7780 0.032 Uiso 1 1 calc R . . C4 C -0.1502(6) 0.44747(16) 0.6578(3) 0.0256(6) Uani 1 1 d . . . H4A H -0.3158 0.4459 0.6060 0.031 Uiso 1 1 calc R . . H4B H -0.1035 0.4965 0.6719 0.031 Uiso 1 1 calc R . . C5 C 0.0457(5) 0.41278(15) 0.5797(3) 0.0226(6) Uani 1 1 d . . . O1A O -0.2623(4) 0.36267(13) 1.0400(2) 0.0368(6) Uani 1 1 d . . . O1B O -0.5930(4) 0.43159(12) 1.0691(2) 0.0291(5) Uani 1 1 d . . . H1 H -0.5933 0.4102 1.1416 0.044 Uiso 1 1 calc R . . O5A O 0.1942(4) 0.36998(13) 0.6275(2) 0.0337(6) Uani 1 1 d . . . O5B O 0.0410(4) 0.43294(12) 0.4536(2) 0.0290(5) Uani 1 1 d . . . H5 H 0.1670 0.4167 0.4182 0.044 Uiso 1 1 calc R . . C22 C -0.4488(5) 0.33005(15) 0.3590(3) 0.0248(6) Uani 1 1 d . . . C24 C -0.1278(6) 0.24876(17) 0.3686(3) 0.0275(7) Uani 1 1 d . . . H24A H 0.0448 0.2680 0.3835 0.033 Uiso 1 1 calc R . . H24B H -0.1177 0.2023 0.3282 0.033 Uiso 1 1 calc R . . C25 C -0.2635(6) 0.24629(16) 0.4988(3) 0.0285(7) Uani 1 1 d . . . H25A H -0.3640 0.2035 0.5049 0.034 Uiso 1 1 calc R . . H25B H -0.1418 0.2498 0.5776 0.034 Uiso 1 1 calc R . . N21 N -0.4268(5) 0.30739(14) 0.4856(3) 0.0303(6) Uani 1 1 d . . . H21 H -0.5007 0.3267 0.5518 0.036 Uiso 1 1 calc R . . N23 N -0.2917(5) 0.29463(14) 0.2855(3) 0.0299(6) Uani 1 1 d . . . H23 H -0.2877 0.2985 0.1986 0.036 Uiso 1 1 calc R . . O22 O -0.5974(4) 0.37721(11) 0.3150(2) 0.0287(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0240(15) 0.0279(16) 0.0236(15) -0.0027(13) 0.0010(12) -0.0024(13) C2 0.0267(16) 0.0262(15) 0.0191(14) -0.0001(11) 0.0017(12) -0.0003(12) C3 0.0265(15) 0.0286(15) 0.0245(15) 0.0023(12) 0.0035(11) 0.0035(13) C4 0.0262(16) 0.0277(15) 0.0233(14) 0.0006(12) 0.0040(12) 0.0027(13) C5 0.0229(15) 0.0247(15) 0.0201(14) 0.0012(11) 0.0010(11) 0.0001(12) O1A 0.0414(14) 0.0426(14) 0.0274(12) 0.0083(10) 0.0099(10) 0.0150(11) O1B 0.0292(12) 0.0331(12) 0.0256(11) 0.0058(9) 0.0074(9) 0.0041(9) O5A 0.0329(13) 0.0458(14) 0.0228(10) 0.0050(10) 0.0043(9) 0.0130(10) O5B 0.0297(13) 0.0360(12) 0.0218(11) 0.0043(9) 0.0051(8) 0.0060(10) C22 0.0254(15) 0.0254(15) 0.0236(15) -0.0007(12) 0.0012(11) -0.0006(12) C24 0.0262(15) 0.0299(16) 0.0262(14) 0.0021(13) 0.0014(12) 0.0044(13) C25 0.0282(16) 0.0285(16) 0.0286(15) 0.0032(13) 0.0004(12) 0.0048(14) N21 0.0355(15) 0.0311(14) 0.0245(14) 0.0017(11) 0.0036(11) 0.0078(12) N23 0.0347(15) 0.0322(14) 0.0229(14) 0.0002(10) 0.0035(11) 0.0087(12) O22 0.0295(11) 0.0331(12) 0.0239(11) 0.0037(9) 0.0042(8) 0.0069(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1A 1.216(4) . ? C1 O1B 1.330(4) . ? C1 C2 1.502(4) . ? C2 C3 1.529(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.505(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O5A 1.219(4) . ? C5 O5B 1.328(4) . ? O1B H1 0.8400 . ? O5B H5 0.8400 . ? C22 O22 1.266(4) . ? C22 N23 1.342(4) . ? C22 N21 1.346(4) . ? C24 N23 1.464(4) . ? C24 C25 1.541(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.467(4) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 123.2(3) . . ? O1A C1 C2 122.9(3) . . ? O1B C1 C2 113.9(3) . . ? C1 C2 C3 111.6(2) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 113.0(3) . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 111.9(2) . . ? C5 C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O5A C5 O5B 123.1(3) . . ? O5A C5 C4 123.2(3) . . ? O5B C5 C4 113.7(2) . . ? C1 O1B H1 109.5 . . ? C5 O5B H5 109.5 . . ? O22 C22 N23 124.8(3) . . ? O22 C22 N21 125.3(3) . . ? N23 C22 N21 109.9(3) . . ? N23 C24 C25 102.3(2) . . ? N23 C24 H24A 111.3 . . ? C25 C24 H24A 111.3 . . ? N23 C24 H24B 111.3 . . ? C25 C24 H24B 111.3 . . ? H24A C24 H24B 109.2 . . ? N21 C25 C24 101.9(2) . . ? N21 C25 H25A 111.4 . . ? C24 C25 H25A 111.4 . . ? N21 C25 H25B 111.4 . . ? C24 C25 H25B 111.4 . . ? H25A C25 H25B 109.3 . . ? C22 N21 C25 111.1(3) . . ? C22 N21 H21 124.4 . . ? C25 N21 H21 124.4 . . ? C22 N23 C24 111.1(3) . . ? C22 N23 H23 124.4 . . ? C24 N23 H23 124.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1B H1 O22 0.84 1.86 2.694(3) 170.5 1_556 O5B H5 O22 0.84 1.85 2.676(3) 169.6 1_655 N21 H21 O5A 0.88 2.02 2.820(3) 150.9 1_455 N23 H23 O1A 0.88 2.04 2.817(3) 147.1 1_554 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.192 _refine_diff_density_min -0.246 _refine_diff_density_rms 0.052 # Attachment '8.cif' data_07skc0003cmcm _database_code_depnum_ccdc_archive 'CCDC 717672' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8 ; _chemical_name_common 8 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H18 N2 O5' _chemical_formula_weight 246.26 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 Cmcm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x, y, -z-1/2' 'x, -y, z-1/2' '-x, y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z-1/2' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, z' _cell_length_a 6.8156(6) _cell_length_b 12.7537(12) _cell_length_c 14.1899(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1233.44(19) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 815 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9842 _exptl_absorpt_correction_T_max 0.9989 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius 95mm CCD camera on \k-goniostat' _diffrn_measurement_method '\f & \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4539 _diffrn_reflns_av_R_equivalents 0.0636 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.19 _diffrn_reflns_theta_max 27.48 _reflns_number_total 800 _reflns_number_gt 578 _reflns_threshold_expression >2\s(I) _computing_data_collection 'COLLECT (Hooft, R.W.W., 1998)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' #Although determined using DirAx, the cell is refined in the HKL #package during data reduction _computing_data_reduction 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' _computing_structure_solution ? _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^ > 2\s(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^)+(0.0213P)^2^+2.1920P] 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_number_reflns 800 _refine_ls_number_parameters 55 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0000 0.3041(2) 0.48515(19) 0.0262(6) Uani 1 2 d S . . C2 C 0.0000 0.3750(2) 0.56975(18) 0.0260(7) Uani 1 2 d S . . H2A H -0.1174 0.4206 0.5675 0.031 Uiso 0.50 1 calc PR . . H2B H 0.1174 0.4206 0.5675 0.031 Uiso 0.50 1 calc PR . . C3 C 0.0000 0.3141(2) 0.66175(17) 0.0238(6) Uani 1 2 d S . . H3A H 0.1172 0.2683 0.6633 0.029 Uiso 0.50 1 calc PR . . H3B H -0.1172 0.2683 0.6633 0.029 Uiso 0.50 1 calc PR . . C4 C 0.0000 0.3831(3) 0.7500 0.0249(9) Uani 1 4 d S . . H4A H -0.1177 0.4286 0.7500 0.030 Uiso 0.50 2 calc SPR . . H4B H 0.1177 0.4286 0.7500 0.030 Uiso 0.50 2 calc SPR . . O1B O 0.0000 0.20910(16) 0.48986(14) 0.0362(6) Uani 1 2 d S . . O1A O 0.0000 0.35654(16) 0.40422(13) 0.0322(6) Uani 1 2 d S . . H1 H 0.0000 0.3139 0.3591 0.048 Uiso 1 2 calc SR . . C22 C 0.0000 0.1399(3) 0.2500 0.0249(9) Uani 1 4 d S . . C25 C 0.0000 -0.0315(2) 0.3045(2) 0.0339(7) Uani 1 2 d S . . H25A H -0.1183 -0.0667 0.3297 0.041 Uiso 0.50 1 calc PR . . H25B H 0.1183 -0.0667 0.3297 0.041 Uiso 0.50 1 calc PR . . N21 N 0.0000 0.07981(19) 0.32741(16) 0.0289(6) Uani 1 2 d S . . H21 H 0.0000 0.1046 0.3853 0.035 Uiso 1 2 calc SR . . O22 O 0.0000 0.2392(2) 0.2500 0.0262(7) Uani 1 4 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0287(16) 0.0272(15) 0.0225(14) 0.0011(12) 0.000 0.000 C2 0.0313(16) 0.0243(15) 0.0223(13) 0.0013(11) 0.000 0.000 C3 0.0304(15) 0.0217(14) 0.0192(13) 0.0011(11) 0.000 0.000 C4 0.029(2) 0.025(2) 0.0209(18) 0.000 0.000 0.000 O1B 0.0610(16) 0.0236(11) 0.0239(11) -0.0005(8) 0.000 0.000 O1A 0.0532(14) 0.0247(11) 0.0188(10) -0.0005(8) 0.000 0.000 C22 0.028(2) 0.021(2) 0.026(2) 0.000 0.000 0.000 C25 0.046(2) 0.0222(15) 0.0336(17) 0.0006(13) 0.000 0.000 N21 0.0404(16) 0.0228(13) 0.0235(12) -0.0001(10) 0.000 0.000 O22 0.0375(18) 0.0209(15) 0.0202(13) 0.000 0.000 0.000 _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1B 1.213(3) . ? C1 O1A 1.329(3) . ? C1 C2 1.503(4) . ? C2 C3 1.519(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.530(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C3 1.530(3) 10_557 ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? O1A H1 0.8400 . ? C22 O22 1.267(5) . ? C22 N21 1.339(3) 10_556 ? C22 N21 1.339(3) . ? C25 N21 1.456(4) . ? C25 C25 1.546(6) 10_556 ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? 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 O1B C1 O1A 123.4(3) . . ? O1B C1 C2 123.8(2) . . ? O1A C1 C2 112.8(2) . . ? C1 C2 C3 112.2(2) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 114.1(2) . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C3 109.8(3) . 10_557 ? C3 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 10_557 . ? C3 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 10_557 . ? H4A C4 H4B 108.2 . . ? C1 O1A H1 109.5 . . ? O22 C22 N21 124.90(17) . 10_556 ? O22 C22 N21 124.90(17) . . ? N21 C22 N21 110.2(3) 10_556 . ? N21 C25 C25 102.93(15) . 10_556 ? N21 C25 H25A 111.2 . . ? C25 C25 H25A 111.2 10_556 . ? N21 C25 H25B 111.2 . . ? C25 C25 H25B 111.2 10_556 . ? H25A C25 H25B 109.1 . . ? C22 N21 C25 112.0(2) . . ? C22 N21 H21 124.0 . . ? C25 N21 H21 124.0 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1 O22 0.84 1.82 2.651(2) 171.3 . N21 H21 O1B 0.88 1.99 2.834(3) 159.2 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.307 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.058 # Attachment '9.cif' data_ssg0307 _database_code_depnum_ccdc_archive 'CCDC 717673' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 9 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H12 N2 O7' _chemical_formula_weight 236.19 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 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 5.3880(13) _cell_length_b 9.921(3) _cell_length_c 18.265(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 976.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 969 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 29.10 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.145 _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 120(2) _diffrn_radiation_wavelength 0.6895 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'fine-slice \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 5 _diffrn_reflns_number 8329 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0258 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 26.59 _reflns_number_total 1290 _reflns_number_gt 1245 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _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^ > 2\s(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^)+(0.0518P)^2^+0.2244P] 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 -10(10) _refine_ls_number_reflns 1290 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0318 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0836 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 C1 C 1.1160(3) 0.60651(18) -0.05341(9) 0.0173(4) Uani 1 1 d . . . C2 C 1.1370(3) 0.52683(18) 0.01826(9) 0.0167(4) Uani 1 1 d . . . H2 H 1.1056 0.5913 0.0593 0.020 Uiso 1 1 calc R . . C3 C 1.4075(4) 0.48047(18) 0.02432(9) 0.0176(4) Uani 1 1 d . . . H3 H 1.5194 0.5605 0.0287 0.021 Uiso 1 1 calc R . . C4 C 1.4361(3) 0.39043(18) 0.09143(9) 0.0180(4) Uani 1 1 d . . . O1A O 1.2387(3) 0.70661(13) -0.06446(7) 0.0235(3) Uani 1 1 d . . . O1B O 0.9569(3) 0.55301(13) -0.10011(7) 0.0228(3) Uani 1 1 d . . . H1 H 0.9611 0.5961 -0.1397 0.052(8) Uiso 1 1 calc R . . O2 O 0.9673(2) 0.42009(12) 0.02580(7) 0.0189(3) Uani 1 1 d . . . H2O H 1.0068 0.3573 -0.0028 0.028 Uiso 1 1 calc R . . O3 O 1.4626(2) 0.40865(15) -0.04033(7) 0.0219(3) Uani 1 1 d . . . H3O H 1.6172 0.4055 -0.0462 0.033 Uiso 1 1 calc R . . O4A O 1.4162(3) 0.45956(13) 0.15306(7) 0.0227(3) Uani 1 1 d . . . H4 H 1.4485 0.4090 0.1887 0.036(7) Uiso 1 1 calc R . . O4B O 1.4731(3) 0.27019(12) 0.08848(7) 0.0221(3) Uani 1 1 d . . . C22 C 0.7533(3) 0.24990(18) 0.26385(9) 0.0184(3) Uani 1 1 d . . . C24 C 1.0941(4) 0.11550(19) 0.29050(10) 0.0230(4) Uani 1 1 d . . . H24A H 1.0601 0.0342 0.3203 0.028 Uiso 1 1 calc R . . H24B H 1.2722 0.1390 0.2945 0.028 Uiso 1 1 calc R . . C25 C 1.0165(4) 0.0951(2) 0.21039(11) 0.0316(5) Uani 1 1 d . . . H25A H 1.1395 0.1349 0.1764 0.038 Uiso 1 1 calc R . . H25B H 0.9957 -0.0017 0.1988 0.038 Uiso 1 1 calc R . . N21 N 0.7804(3) 0.16654(17) 0.20687(8) 0.0251(4) Uani 1 1 d . . . H21 H 0.6700 0.1561 0.1718 0.073(11) Uiso 1 1 calc R . . N23 N 0.9358(3) 0.22816(16) 0.31232(8) 0.0244(4) Uani 1 1 d . . . H23 H 0.9577 0.2759 0.3524 0.039(7) Uiso 1 1 calc R . . O22 O 0.5820(2) 0.33567(13) 0.27099(7) 0.0221(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0142(8) 0.0218(8) 0.0160(7) 0.0004(6) 0.0019(6) 0.0038(7) C2 0.0145(8) 0.0209(8) 0.0148(7) -0.0002(6) -0.0004(6) 0.0002(7) C3 0.0149(8) 0.0218(8) 0.0161(8) 0.0000(7) -0.0010(6) 0.0000(7) C4 0.0124(8) 0.0240(8) 0.0174(7) 0.0005(6) -0.0022(7) -0.0008(7) O1A 0.0243(7) 0.0241(6) 0.0221(6) 0.0049(5) 0.0003(6) -0.0026(6) O1B 0.0240(7) 0.0279(6) 0.0164(6) 0.0037(5) -0.0052(5) -0.0018(6) O2 0.0155(6) 0.0202(6) 0.0209(6) 0.0002(5) 0.0012(5) -0.0012(5) O3 0.0148(6) 0.0334(7) 0.0175(6) -0.0014(5) 0.0024(5) 0.0043(6) O4A 0.0269(7) 0.0243(6) 0.0169(6) -0.0011(5) -0.0057(5) 0.0043(6) O4B 0.0234(7) 0.0224(6) 0.0204(6) -0.0001(5) -0.0036(5) 0.0040(6) C22 0.0192(8) 0.0205(8) 0.0156(7) 0.0022(6) 0.0005(7) -0.0019(7) C24 0.0184(9) 0.0276(9) 0.0230(8) 0.0018(7) -0.0025(7) 0.0028(8) C25 0.0331(11) 0.0380(11) 0.0238(9) -0.0052(8) -0.0053(8) 0.0173(10) N21 0.0257(8) 0.0304(8) 0.0192(7) -0.0058(6) -0.0052(6) 0.0090(8) N23 0.0265(8) 0.0266(7) 0.0200(7) -0.0036(6) -0.0066(7) 0.0043(7) O22 0.0225(6) 0.0275(6) 0.0164(5) -0.0011(5) -0.0004(5) 0.0054(6) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1A 1.210(2) . ? C1 O1B 1.321(2) . ? C1 C2 1.533(2) . ? C2 O2 1.406(2) . ? C2 C3 1.533(2) . ? C2 H2 1.0000 . ? C3 O3 1.411(2) . ? C3 C4 1.525(2) . ? C3 H3 1.0000 . ? C4 O4B 1.211(2) . ? C4 O4A 1.323(2) . ? O1B H1 0.8400 . ? O2 H2O 0.8400 . ? O3 H3O 0.8400 . ? O4A H4 0.8400 . ? C22 O22 1.262(2) . ? C22 N21 1.337(2) . ? C22 N23 1.341(2) . ? C24 N23 1.461(2) . ? C24 C25 1.535(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 N21 1.458(3) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? N21 H21 0.8800 . ? N23 H23 0.8800 . ? 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 O1A C1 O1B 125.23(16) . . ? O1A C1 C2 121.69(16) . . ? O1B C1 C2 113.08(15) . . ? O2 C2 C3 112.67(14) . . ? O2 C2 C1 115.09(15) . . ? C3 C2 C1 106.65(14) . . ? O2 C2 H2 107.4 . . ? C3 C2 H2 107.4 . . ? C1 C2 H2 107.4 . . ? O3 C3 C4 110.84(15) . . ? O3 C3 C2 106.94(14) . . ? C4 C3 C2 109.26(14) . . ? O3 C3 H3 109.9 . . ? C4 C3 H3 109.9 . . ? C2 C3 H3 109.9 . . ? O4B C4 O4A 124.21(16) . . ? O4B C4 C3 123.93(16) . . ? O4A C4 C3 111.86(15) . . ? C1 O1B H1 109.5 . . ? C2 O2 H2O 109.5 . . ? C3 O3 H3O 109.5 . . ? C4 O4A H4 109.5 . . ? O22 C22 N21 125.24(16) . . ? O22 C22 N23 125.22(16) . . ? N21 C22 N23 109.54(16) . . ? N23 C24 C25 101.64(15) . . ? N23 C24 H24A 111.4 . . ? C25 C24 H24A 111.4 . . ? N23 C24 H24B 111.4 . . ? C25 C24 H24B 111.4 . . ? H24A C24 H24B 109.3 . . ? N21 C25 C24 102.46(15) . . ? N21 C25 H25A 111.3 . . ? C24 C25 H25A 111.3 . . ? N21 C25 H25B 111.3 . . ? C24 C25 H25B 111.3 . . ? H25A C25 H25B 109.2 . . ? C22 N21 C25 111.18(15) . . ? C22 N21 H21 124.4 . . ? C25 N21 H21 124.4 . . ? C22 N23 C24 111.78(15) . . ? C22 N23 H23 124.1 . . ? C24 N23 H23 124.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1B H1 O22 0.84 1.78 2.6090(18) 167.9 2_664 O2 H2O O4B 0.84 2.02 2.8145(18) 157.3 4_455 O3 H3O O2 0.84 2.30 2.977(2) 137.5 1_655 O3 H3O O1B 0.84 2.54 3.215(2) 137.9 1_655 O4A H4 O22 0.84 1.82 2.6359(18) 164.1 1_655 N21 H21 O4B 0.88 2.17 2.911(2) 141.1 1_455 N23 H23 O1A 0.88 2.24 2.926(2) 134.7 2_765 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 26.59 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.341 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.041