data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Santiago Uriel' _publ_contact_author_email SURIEL@UNIZAR.ES _publ_section_title ; SUPRAMOLECULAR ARRANGEMENTS BASED ON CYCLOHEXANE-5-SPIROHYDANTOIN DERIVATIVES ; loop_ _publ_author_name 'Santiago Uriel' 'Diego Casabona' 'C Cativiela' 'Sara Graus' 'J Serrano' # Attachment 'Compound (1).CIF' data_Compound1 _database_code_depnum_ccdc_archive 'CCDC 762369' #TrackingRef 'Compound (1).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H14 N2 O3' _chemical_formula_weight 198.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.1273(18) _cell_length_b 6.5676(12) _cell_length_c 14.1016(19) _cell_angle_alpha 90.00 _cell_angle_beta 101.282(6) _cell_angle_gamma 90.00 _cell_volume 1010.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.303 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.099 _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 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_decay_% ? _diffrn_reflns_number 3061 _diffrn_reflns_av_R_equivalents 0.0141 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 30.01 _reflns_number_total 2927 _reflns_number_gt 1954 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0852P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2927 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1253 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.42235(11) -0.16306(19) 0.07869(8) 0.0363(3) Uani 1 1 d . . . HN1 H 0.4165(15) -0.154(3) 0.0146(12) 0.039(4) Uiso 1 1 d . . . O1 O 0.57629(10) 0.07583(16) 0.12073(7) 0.0433(3) Uani 1 1 d . . . C1 C 0.50317(13) -0.0499(2) 0.13999(9) 0.0337(3) Uani 1 1 d . . . N2 N 0.48918(12) -0.0981(2) 0.23360(9) 0.0399(3) Uani 1 1 d . . . HN2 H 0.5349(16) -0.044(3) 0.2848(13) 0.048(5) Uiso 1 1 d . . . O2 O 0.36572(12) -0.30797(19) 0.30437(7) 0.0534(3) Uani 1 1 d . . . C2 C 0.39953(14) -0.2398(2) 0.23387(9) 0.0364(3) Uani 1 1 d . . . O3 O 0.13541(11) -0.60994(16) -0.11242(8) 0.0506(3) Uani 1 1 d . . . C3 C 0.34993(12) -0.2988(2) 0.12809(9) 0.0311(3) Uani 1 1 d . . . C4 C 0.21180(14) -0.2580(3) 0.09923(12) 0.0403(3) Uani 1 1 d . . . H4A H 0.1995(16) -0.114(3) 0.1057(12) 0.049(5) Uiso 1 1 d . . . H4B H 0.1718(18) -0.336(3) 0.1463(14) 0.061(6) Uiso 1 1 d . . . C5 C 0.16097(14) -0.3316(2) -0.00361(12) 0.0399(3) Uani 1 1 d . . . H5A H 0.072(2) -0.309(3) -0.0163(14) 0.063(6) Uiso 1 1 d . . . H5B H 0.1985(16) -0.256(3) -0.0530(13) 0.048(5) Uiso 1 1 d . . . C6 C 0.18737(13) -0.5557(2) -0.01459(10) 0.0346(3) Uani 1 1 d . . . H6 H 0.1515(15) -0.641(3) 0.0308(12) 0.041(4) Uiso 1 1 d . . . C7 C 0.32484(14) -0.5945(2) 0.01030(11) 0.0368(3) Uani 1 1 d . . . H7A H 0.3637(16) -0.514(3) -0.0362(13) 0.053(5) Uiso 1 1 d . . . H7B H 0.3436(16) -0.741(3) 0.0066(12) 0.048(5) Uiso 1 1 d . . . C8 C 0.37741(13) -0.5247(2) 0.11354(10) 0.0346(3) Uani 1 1 d . . . H8A H 0.3414(15) -0.606(2) 0.1615(12) 0.041(4) Uiso 1 1 d . . . H8B H 0.4696(17) -0.542(3) 0.1286(13) 0.049(5) Uiso 1 1 d . . . C9 C 0.1283(2) -0.8238(3) -0.13085(19) 0.0702(7) Uani 1 1 d . . . H9A H 0.212(3) -0.883(4) -0.1223(19) 0.104(9) Uiso 1 1 d . . . H9B H 0.085(3) -0.840(4) -0.196(2) 0.111(9) Uiso 1 1 d . . . H9C H 0.086(3) -0.897(6) -0.082(3) 0.158(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0431(7) 0.0415(7) 0.0238(5) -0.0003(5) 0.0051(5) -0.0104(6) O1 0.0469(6) 0.0467(6) 0.0349(5) 0.0029(5) 0.0045(4) -0.0145(5) C1 0.0373(7) 0.0358(7) 0.0270(6) 0.0016(5) 0.0041(5) -0.0012(6) N2 0.0476(7) 0.0463(7) 0.0240(5) -0.0023(5) 0.0028(5) -0.0121(6) O2 0.0727(8) 0.0602(8) 0.0307(5) 0.0001(5) 0.0183(5) -0.0166(6) C2 0.0436(8) 0.0391(7) 0.0268(6) -0.0002(6) 0.0073(6) -0.0016(6) O3 0.0634(7) 0.0367(6) 0.0401(6) -0.0035(5) -0.0181(5) 0.0056(5) C3 0.0341(7) 0.0343(7) 0.0254(6) 0.0000(5) 0.0067(5) -0.0028(6) C4 0.0362(8) 0.0407(9) 0.0445(8) -0.0087(7) 0.0091(6) 0.0040(6) C5 0.0327(7) 0.0385(8) 0.0446(8) -0.0024(7) -0.0018(6) 0.0070(6) C6 0.0349(7) 0.0342(7) 0.0314(6) 0.0012(6) -0.0017(5) -0.0004(6) C7 0.0374(8) 0.0352(7) 0.0357(7) -0.0039(6) 0.0023(6) 0.0063(6) C8 0.0329(7) 0.0365(7) 0.0322(7) 0.0013(6) 0.0012(5) 0.0026(6) C9 0.0788(15) 0.0422(10) 0.0728(14) -0.0186(10) -0.0265(12) 0.0093(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.3433(18) . ? N1 C3 1.4658(17) . ? O1 C1 1.2263(17) . ? C1 N2 1.3954(17) . ? N2 C2 1.3649(19) . ? O2 C2 1.2154(17) . ? C2 C3 1.5354(18) . ? O3 C9 1.428(2) . ? O3 C6 1.4327(17) . ? C3 C4 1.535(2) . ? C3 C8 1.537(2) . ? C4 C5 1.528(2) . ? C5 C6 1.514(2) . ? C6 C7 1.522(2) . ? C7 C8 1.529(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C3 113.05(11) . . ? O1 C1 N1 128.29(13) . . ? O1 C1 N2 124.32(13) . . ? N1 C1 N2 107.38(12) . . ? C2 N2 C1 111.97(12) . . ? O2 C2 N2 126.65(13) . . ? O2 C2 C3 126.29(14) . . ? N2 C2 C3 107.06(11) . . ? C9 O3 C6 114.69(13) . . ? N1 C3 C4 112.53(12) . . ? N1 C3 C2 100.48(11) . . ? C4 C3 C2 111.39(12) . . ? N1 C3 C8 112.42(11) . . ? C4 C3 C8 110.37(12) . . ? C2 C3 C8 109.28(11) . . ? C5 C4 C3 111.22(12) . . ? C6 C5 C4 111.19(13) . . ? O3 C6 C5 106.88(11) . . ? O3 C6 C7 112.23(12) . . ? C5 C6 C7 110.21(12) . . ? C6 C7 C8 110.43(12) . . ? C7 C8 C3 111.56(12) . . ? 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 N1 HN1 O1 0.894(17) 1.994(17) 2.8728(16) 167.1(16) 3_655 N2 HN2 O3 0.872(19) 1.935(19) 2.8011(16) 171.8(17) 4_656 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.199 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.042 # Attachment 'Compound (3).CIF' data_Compound3 _database_code_depnum_ccdc_archive 'CCDC 762370' #TrackingRef 'Compound (3).CIF' _audit_creation_date ; 'Tue Aug 01 10:40:49 2006' ; _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 N2 O4' _chemical_formula_weight 240.26 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.6196(7) _cell_length_b 6.3329(4) _cell_length_c 15.4169(10) _cell_angle_alpha 90.00 _cell_angle_beta 92.831(5) _cell_angle_gamma 90.00 _cell_volume 1133.08(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.997 _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.3990 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5582 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0442 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.90 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2246 _reflns_number_gt 1786 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'Brucker SHELXTL' _computing_structure_refinement 'Brucker SHELXTL' _computing_molecular_graphics 'Brucker SHELXTL' _computing_publication_material 'Brucker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0050P)^2^+0.7797P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2246 _refine_ls_number_parameters 218 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _refine_ls_shift/su_max 0.002 _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 N1 N 0.57470(14) 0.1593(3) -0.07689(11) 0.0168(4) Uani 1 1 d . . . HN1 H 0.5792(19) 0.147(4) -0.0219(17) 0.033(7) Uiso 1 1 d . . . O1 O 0.42968(11) -0.0853(2) -0.10394(8) 0.0197(3) Uani 1 1 d . . . C1 C 0.50223(15) 0.0416(3) -0.12657(12) 0.0155(4) Uani 1 1 d . . . N2 N 0.52370(14) 0.0852(3) -0.21270(11) 0.0176(4) Uani 1 1 d . . . HN2 H 0.4851(17) 0.037(3) -0.2561(15) 0.021(6) Uiso 1 1 d . . . O2 O 0.64906(11) 0.2942(2) -0.28596(8) 0.0211(3) Uani 1 1 d . . . C2 C 0.61041(15) 0.2286(3) -0.21950(12) 0.0161(4) Uani 1 1 d . . . O3 O 0.89913(12) 0.5137(2) 0.13004(9) 0.0261(4) Uani 1 1 d . . . C3 C 0.65092(15) 0.2894(3) -0.12740(12) 0.0158(4) Uani 1 1 d . . . O4 O 0.86988(12) 0.8336(2) 0.07106(9) 0.0235(3) Uani 1 1 d . . . C4 C 0.63229(17) 0.5259(3) -0.11250(13) 0.0173(4) Uani 1 1 d . . . H4A H 0.6691(17) 0.603(3) -0.1588(14) 0.023(5) Uiso 1 1 d . . . H4B H 0.5480(18) 0.559(3) -0.1186(13) 0.022(5) Uiso 1 1 d . . . C5 C 0.68209(16) 0.5993(3) -0.02391(13) 0.0181(4) Uani 1 1 d . . . H5A H 0.6370(16) 0.524(3) 0.0235(13) 0.013(5) Uiso 1 1 d . . . H5B H 0.6709(16) 0.751(3) -0.0181(13) 0.017(5) Uiso 1 1 d . . . C6 C 0.81064(16) 0.5430(3) -0.01397(13) 0.0159(4) Uani 1 1 d . . . H6A H 0.8512(16) 0.616(3) -0.0608(12) 0.013(5) Uiso 1 1 d . . . C7 C 0.82562(17) 0.3050(3) -0.02288(13) 0.0168(4) Uani 1 1 d . . . H7A H 0.7834(16) 0.238(3) 0.0239(13) 0.017(5) Uiso 1 1 d . . . H7B H 0.9076(18) 0.273(3) -0.0149(13) 0.022(5) Uiso 1 1 d . . . C8 C 0.77801(16) 0.2311(3) -0.11135(13) 0.0175(4) Uani 1 1 d . . . H8A H 0.7852(17) 0.079(3) -0.1177(13) 0.022(5) Uiso 1 1 d . . . H8B H 0.8205(17) 0.299(3) -0.1592(14) 0.025(6) Uiso 1 1 d . . . C9 C 0.86393(16) 0.6236(3) 0.07043(13) 0.0170(4) Uani 1 1 d . . . C10 C 0.92122(18) 0.9344(3) 0.14915(14) 0.0230(5) Uani 1 1 d . . . H10A H 0.9840(17) 0.848(3) 0.1691(13) 0.017(5) Uiso 1 1 d . . . H10B H 0.9485(17) 1.073(4) 0.1289(13) 0.024(6) Uiso 1 1 d . . . C11 C 0.8349(2) 0.9592(4) 0.21692(17) 0.0314(5) Uani 1 1 d . . . H11A H 0.815(2) 0.822(4) 0.2394(17) 0.046(7) Uiso 1 1 d . . . H11B H 0.8690(19) 1.052(4) 0.2650(16) 0.038(7) Uiso 1 1 d . . . H11C H 0.763(2) 1.026(4) 0.1895(16) 0.048(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0199(9) 0.0200(9) 0.0104(9) 0.0009(7) 0.0000(7) -0.0039(7) O1 0.0198(7) 0.0209(7) 0.0185(7) 0.0012(6) -0.0002(5) -0.0049(6) C1 0.0164(9) 0.0138(9) 0.0162(10) -0.0003(8) -0.0005(8) 0.0037(8) N2 0.0206(9) 0.0184(9) 0.0133(9) 0.0007(7) -0.0033(7) -0.0028(7) O2 0.0243(7) 0.0214(7) 0.0176(7) 0.0021(6) 0.0024(6) -0.0009(6) C2 0.0169(10) 0.0136(9) 0.0177(10) 0.0011(8) 0.0005(8) 0.0035(8) O3 0.0375(9) 0.0194(7) 0.0202(8) 0.0021(6) -0.0096(6) 0.0036(6) C3 0.0166(9) 0.0163(9) 0.0147(10) 0.0028(8) 0.0009(8) -0.0009(8) O4 0.0301(8) 0.0172(7) 0.0223(8) -0.0009(6) -0.0086(6) -0.0033(6) C4 0.0157(10) 0.0164(10) 0.0196(11) -0.0001(8) -0.0014(8) 0.0017(8) C5 0.0178(10) 0.0148(10) 0.0214(11) -0.0017(9) -0.0016(8) 0.0022(8) C6 0.0168(10) 0.0152(10) 0.0155(10) 0.0030(8) -0.0003(8) 0.0003(8) C7 0.0130(10) 0.0174(10) 0.0199(10) 0.0004(9) -0.0010(8) 0.0033(8) C8 0.0186(10) 0.0164(10) 0.0175(10) -0.0013(9) 0.0006(8) 0.0025(8) C9 0.0145(9) 0.0162(10) 0.0203(11) 0.0009(9) 0.0004(8) 0.0003(8) C10 0.0251(11) 0.0191(11) 0.0238(12) -0.0021(9) -0.0092(9) -0.0032(9) C11 0.0282(13) 0.0315(13) 0.0339(14) -0.0125(11) -0.0026(10) -0.0006(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.337(2) . ? N1 C3 1.462(2) . ? O1 C1 1.228(2) . ? C1 N2 1.391(2) . ? N2 C2 1.364(2) . ? O2 C2 1.212(2) . ? C2 C3 1.523(3) . ? O3 C9 1.208(2) . ? C3 C8 1.531(3) . ? C3 C4 1.532(3) . ? O4 C9 1.332(2) . ? O4 C10 1.464(2) . ? C4 C5 1.529(3) . ? C5 C6 1.536(3) . ? C6 C9 1.503(3) . ? C6 C7 1.524(3) . ? C7 C8 1.520(3) . ? C10 C11 1.492(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C3 112.95(16) . . ? O1 C1 N1 128.61(18) . . ? O1 C1 N2 124.00(17) . . ? N1 C1 N2 107.38(16) . . ? C2 N2 C1 111.92(16) . . ? O2 C2 N2 126.79(18) . . ? O2 C2 C3 126.21(17) . . ? N2 C2 C3 106.99(15) . . ? N1 C3 C2 100.75(14) . . ? N1 C3 C8 112.51(16) . . ? C2 C3 C8 109.94(15) . . ? N1 C3 C4 112.16(15) . . ? C2 C3 C4 110.35(15) . . ? C8 C3 C4 110.73(16) . . ? C9 O4 C10 117.42(16) . . ? C5 C4 C3 112.40(16) . . ? C4 C5 C6 109.98(16) . . ? C9 C6 C7 111.72(16) . . ? C9 C6 C5 111.38(16) . . ? C7 C6 C5 109.59(15) . . ? C8 C7 C6 110.33(16) . . ? C7 C8 C3 112.10(16) . . ? O3 C9 O4 123.68(18) . . ? O3 C9 C6 124.93(17) . . ? O4 C9 C6 111.38(17) . . ? O4 C10 C11 111.17(17) . . ? 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 N1 HN1 O1 0.85(2) 1.99(3) 2.830(2) 171(2) 3_655 N2 HN2 O3 0.84(2) 2.00(2) 2.832(2) 167(2) 4_565 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.231 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.041 # Attachment 'Compound (4).CIF' data_compound _database_code_depnum_ccdc_archive 'CCDC 762371' #TrackingRef 'Compound (4).CIF' _audit_creation_date ; 'Tue Aug 01 10:40:49 2006' ; _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H20 N2 O2' _chemical_formula_weight 224.30 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 6.169(2) _cell_length_b 6.177(2) _cell_length_c 17.569(9) _cell_angle_alpha 84.46(4) _cell_angle_beta 86.65(4) _cell_angle_gamma 66.44(2) _cell_volume 610.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1265 _cell_measurement_theta_min 3.4726 _cell_measurement_theta_max 21.7617 _exptl_crystal_description Plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.220 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_min 0.976 _exptl_absorpt_correction_T_max 0.997 _exptl_special_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET) (compiled Apr 13 2006,12:24:59) ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.3990 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5050 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 23.26 _diffrn_reflns_reduction_process ? _reflns_number_total 1616 _reflns_number_gt 823 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'Brucker SHELXTL' _computing_structure_refinement 'Brucker SHELXTL' _computing_molecular_graphics 'Brucker SHELXTL' _computing_publication_material 'Brucker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1494P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1616 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1480 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2554 _refine_ls_wR_factor_gt 0.2293 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.3430(9) 0.8441(8) 0.5745(3) 0.0455(14) Uani 1 1 d . . . HN1 H 0.430(12) 0.915(11) 0.591(3) 0.065(19) Uiso 1 1 d . . . O1 O 0.3620(7) 0.8879(7) 0.4429(2) 0.0526(13) Uani 1 1 d . . . C1 C 0.3055(10) 0.8161(9) 0.5051(4) 0.0389(16) Uani 1 1 d . . . N2 N 0.1716(9) 0.6721(8) 0.5104(3) 0.0432(14) Uani 1 1 d . . . HN2 H 0.107(9) 0.650(8) 0.466(3) 0.038(15) Uiso 1 1 d . . . O2 O 0.0232(8) 0.4905(7) 0.6061(2) 0.0630(14) Uani 1 1 d . . . C2 C 0.1319(10) 0.6136(9) 0.5830(4) 0.0406(15) Uani 1 1 d . . . C3 C 0.2492(10) 0.7244(9) 0.6338(3) 0.0410(16) Uani 1 1 d . . . C4 C 0.4439(12) 0.5321(10) 0.6800(3) 0.0546(18) Uani 1 1 d . . . H4A H 0.3823 0.4209 0.7051 0.065 Uiso 1 1 calc R . . H4B H 0.5715 0.4464 0.6455 0.065 Uiso 1 1 calc R . . C5 C 0.5412(12) 0.6259(11) 0.7393(4) 0.0577(19) Uani 1 1 d . . . H5A H 0.6208 0.7213 0.7141 0.069 Uiso 1 1 calc R . . H5B H 0.6572 0.4941 0.7689 0.069 Uiso 1 1 calc R . . C6 C 0.3499(13) 0.7744(11) 0.7927(3) 0.0563(19) Uani 1 1 d . . . H6 H 0.2675 0.6743 0.8136 0.068 Uiso 1 1 calc R . . C7 C 0.1707(13) 0.9772(11) 0.7451(4) 0.0598(19) Uani 1 1 d . . . H7A H 0.2466 1.0761 0.7199 0.072 Uiso 1 1 calc R . . H7B H 0.0450 1.0735 0.7783 0.072 Uiso 1 1 calc R . . C8 C 0.0655(12) 0.8886(11) 0.6853(3) 0.0561(18) Uani 1 1 d . . . H8A H -0.0266 0.8062 0.7109 0.067 Uiso 1 1 calc R . . H8B H -0.0412 1.0235 0.6542 0.067 Uiso 1 1 calc R . . C9 C 0.4339(14) 0.8525(12) 0.8630(4) 0.066(2) Uani 1 1 d . . . C10 C 0.5372(18) 1.0326(15) 0.8412(4) 0.103(3) Uani 1 1 d . . . H10A H 0.6677 0.9691 0.8059 0.154 Uiso 1 1 calc R . . H10B H 0.5915 1.0708 0.8861 0.154 Uiso 1 1 calc R . . H10C H 0.4185 1.1733 0.8175 0.154 Uiso 1 1 calc R . . C11 C 0.233(2) 0.950(2) 0.9200(5) 0.135(4) Uani 1 1 d . . . H11C H 0.1713 0.8320 0.9356 0.203 Uiso 1 1 calc R . . H11B H 0.1106 1.0882 0.8969 0.203 Uiso 1 1 calc R . . H11A H 0.2902 0.9909 0.9639 0.203 Uiso 1 1 calc R . . C12 C 0.621(2) 0.6326(16) 0.9045(5) 0.139(5) Uani 1 1 d . . . H12C H 0.7528 0.5620 0.8702 0.209 Uiso 1 1 calc R . . H12B H 0.5533 0.5202 0.9210 0.209 Uiso 1 1 calc R . . H12A H 0.6746 0.6784 0.9481 0.209 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.054(3) 0.054(3) 0.048(4) -0.008(2) -0.005(3) -0.040(3) O1 0.062(3) 0.059(3) 0.055(3) 0.002(2) -0.004(2) -0.044(2) C1 0.035(4) 0.031(3) 0.056(5) -0.004(3) -0.005(3) -0.017(3) N2 0.049(3) 0.052(3) 0.045(4) -0.007(2) -0.002(3) -0.036(3) O2 0.079(3) 0.075(3) 0.070(3) -0.004(2) -0.002(3) -0.068(3) C2 0.038(4) 0.038(3) 0.049(4) -0.009(3) 0.000(3) -0.016(3) C3 0.036(4) 0.041(3) 0.056(4) -0.004(3) -0.003(3) -0.026(3) C4 0.057(4) 0.048(4) 0.063(4) -0.017(3) 0.002(4) -0.022(3) C5 0.055(5) 0.059(4) 0.061(5) -0.012(3) -0.006(4) -0.022(4) C6 0.076(5) 0.058(4) 0.056(4) 0.000(3) -0.005(4) -0.049(4) C7 0.065(5) 0.059(4) 0.066(5) -0.012(3) -0.005(4) -0.033(4) C8 0.051(4) 0.062(4) 0.063(5) -0.010(3) -0.003(4) -0.028(4) C9 0.082(6) 0.077(5) 0.056(5) -0.005(4) -0.012(4) -0.050(4) C10 0.158(9) 0.125(7) 0.079(6) -0.015(5) -0.008(6) -0.111(7) C11 0.134(9) 0.232(12) 0.084(7) -0.078(7) 0.027(7) -0.109(9) C12 0.219(13) 0.097(7) 0.093(7) 0.004(5) -0.083(8) -0.046(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.294(7) . ? N1 C3 1.446(7) . ? O1 C1 1.224(7) . ? C1 N2 1.430(7) . ? N2 C2 1.329(7) . ? O2 C2 1.229(7) . ? C2 C3 1.541(7) . ? C3 C8 1.507(8) . ? C3 C4 1.517(8) . ? C4 C5 1.499(8) . ? C5 C6 1.512(9) . ? C6 C7 1.514(9) . ? C6 C9 1.555(8) . ? C7 C8 1.515(8) . ? C9 C10 1.499(9) . ? C9 C11 1.507(11) . ? C9 C12 1.538(11) . ? 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 N1 C3 115.5(5) . . ? O1 C1 N1 132.3(5) . . ? O1 C1 N2 121.0(6) . . ? N1 C1 N2 106.7(6) . . ? C2 N2 C1 110.7(6) . . ? O2 C2 N2 126.2(5) . . ? O2 C2 C3 125.6(6) . . ? N2 C2 C3 108.1(5) . . ? N1 C3 C8 114.0(5) . . ? N1 C3 C4 111.9(5) . . ? C8 C3 C4 111.0(5) . . ? N1 C3 C2 99.0(5) . . ? C8 C3 C2 109.9(5) . . ? C4 C3 C2 110.4(4) . . ? C5 C4 C3 113.3(5) . . ? C4 C5 C6 112.1(5) . . ? C5 C6 C7 108.0(5) . . ? C5 C6 C9 116.5(6) . . ? C7 C6 C9 113.8(5) . . ? C6 C7 C8 111.6(5) . . ? C3 C8 C7 113.2(5) . . ? C10 C9 C11 109.4(7) . . ? C10 C9 C12 109.2(8) . . ? C11 C9 C12 106.1(8) . . ? C10 C9 C6 112.6(6) . . ? C11 C9 C6 110.8(6) . . ? C12 C9 C6 108.6(6) . . ? 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 N1 HN1 O1 0.89(7) 2.12(7) 2.897(6) 145(5) 2_676 N2 HN2 O2 0.94(5) 1.97(6) 2.879(7) 161(4) 2_566 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.305 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.061 # Attachment 'Compound (5).CIF' data_compound5 _database_code_depnum_ccdc_archive 'CCDC 762372' #TrackingRef 'Compound (5).CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H12 N2 O4' _chemical_formula_weight 212.21 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 0.0016 '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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x, -y, z' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z' _cell_length_a 10.410(3) _cell_length_b 6.865(2) _cell_length_c 14.194(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.170(10) _cell_angle_gamma 90.00 _cell_volume 979.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 100 _cell_measurement_theta_min 5.812 _cell_measurement_theta_max 34.343 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max .19 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.981 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details 'Siemens SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1288 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0629 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 24.96 _reflns_number_total 942 _reflns_number_gt 526 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+2.0154P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 942 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1226 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1330 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.3926(3) 0.0000 0.5765(2) 0.0423(11) Uani 1 2 d S . . N1 N 0.3252(4) 0.0000 0.4066(3) 0.0426(13) Uani 1 2 d S . . HN1 H 0.408(5) 0.0000 0.398(4) 0.061(18) Uiso 1 2 d S . . C1 C 0.3079(4) 0.0000 0.4977(3) 0.0361(13) Uani 1 2 d S . . O2 O -0.0235(3) 0.0000 0.3615(2) 0.0411(10) Uani 1 2 d S . . N2 N 0.1697(4) 0.0000 0.4874(3) 0.0336(11) Uani 1 2 d S . . HN2 H 0.130(5) 0.0000 0.541(4) 0.059(17) Uiso 1 2 d S . . C2 C 0.0977(5) 0.0000 0.3909(3) 0.0321(12) Uani 1 2 d S . . C3 C 0.1992(4) 0.0000 0.3281(3) 0.0323(13) Uani 1 2 d S . . O3 O 0.4118(3) 0.1619(5) 0.0527(2) 0.0795(12) Uani 1 1 d . . . H3 H 0.450(6) 0.158(13) 0.004(7) 0.07(3) Uiso 0.50 1 d P . . C4 C 0.1836(4) 0.1831(6) 0.2640(3) 0.0398(10) Uani 1 1 d . . . H4A H 0.189(3) 0.309(6) 0.304(3) 0.056(12) Uiso 1 1 d . . . H4B H 0.091(3) 0.182(6) 0.223(3) 0.048(11) Uiso 1 1 d . . . C5 C 0.2833(4) 0.1839(6) 0.2006(3) 0.0415(10) Uani 1 1 d . . . H5A H 0.267(3) 0.306(6) 0.159(2) 0.040(10) Uiso 1 1 d . . . H5B H 0.377(3) 0.195(6) 0.245(2) 0.050(11) Uiso 1 1 d . . . C6 C 0.2714(5) 0.0000 0.1382(4) 0.0342(13) Uani 1 2 d S . . H6 H 0.189(5) 0.0000 0.092(4) 0.057(17) Uiso 1 2 d S . . C7 C 0.3723(5) 0.0000 0.0772(4) 0.0408(14) 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 O1 0.0282(17) 0.072(3) 0.0265(18) 0.000 0.0064(15) 0.000 N1 0.024(2) 0.080(4) 0.026(2) 0.000 0.0100(18) 0.000 C1 0.031(3) 0.051(4) 0.028(3) 0.000 0.011(2) 0.000 O2 0.0215(18) 0.072(3) 0.0309(18) 0.000 0.0085(14) 0.000 N2 0.023(2) 0.054(3) 0.027(2) 0.000 0.0120(17) 0.000 C2 0.031(3) 0.041(3) 0.030(3) 0.000 0.016(2) 0.000 C3 0.022(2) 0.050(4) 0.027(2) 0.000 0.009(2) 0.000 O3 0.109(3) 0.065(2) 0.096(2) -0.003(2) 0.083(2) -0.010(2) C4 0.041(2) 0.048(3) 0.036(2) 0.001(2) 0.0211(17) 0.005(2) C5 0.048(2) 0.046(3) 0.038(2) -0.002(2) 0.0245(18) -0.004(2) C6 0.034(3) 0.044(4) 0.029(3) 0.000 0.017(2) 0.000 C7 0.040(3) 0.052(4) 0.033(3) 0.000 0.014(2) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.231(5) . ? N1 C1 1.351(6) . ? N1 C3 1.482(6) . ? C1 N2 1.407(5) . ? O2 C2 1.221(5) . ? N2 C2 1.378(6) . ? C2 C3 1.550(6) . ? C3 C4 1.536(4) 6 ? C3 C4 1.536(4) . ? O3 C7 1.265(4) . ? C4 C5 1.541(4) . ? C5 C6 1.528(5) . ? C6 C7 1.526(6) . ? C6 C5 1.528(5) 6 ? C7 O3 1.265(4) 6 ? 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 N1 C3 113.9(4) . . ? O1 C1 N1 128.8(4) . . ? O1 C1 N2 124.4(4) . . ? N1 C1 N2 106.8(4) . . ? C2 N2 C1 112.3(4) . . ? O2 C2 N2 125.7(4) . . ? O2 C2 C3 127.1(4) . . ? N2 C2 C3 107.2(4) . . ? N1 C3 C4 112.4(2) . 6 ? N1 C3 C4 112.4(2) . . ? C4 C3 C4 109.9(4) 6 . ? N1 C3 C2 99.8(3) . . ? C4 C3 C2 111.0(2) 6 . ? C4 C3 C2 111.0(2) . . ? C3 C4 C5 111.5(3) . . ? C6 C5 C4 111.8(3) . . ? C7 C6 C5 111.4(3) . . ? C7 C6 C5 111.4(3) . 6 ? C5 C6 C5 111.4(4) . 6 ? O3 C7 O3 122.9(5) . 6 ? O3 C7 C6 118.6(2) . . ? O3 C7 C6 118.6(2) 6 . ? 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 N1 HN1 O1 0.90(5) 2.02(5) 2.885(5) 163(5) 5_656 N2 HN2 O2 0.96(5) 1.98(5) 2.937(5) 172(4) 5_556 O3 H3 O3 0.88(8) 1.83(7) 2.654(5) 156(8) 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.251 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.059