# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Wolf-Walther du Mont' _publ_contact_author_email W.DU-MONT@TU-BS.DE _publ_section_title ; 5-Selenization of Salicylic Acid Derivatives Yielded Isoform-specific 5-Lipoxygenase Inhibitors ; loop_ _publ_author_name 'Wolf-Walther du Mont' 'Constantin Daniliuc' 'Igor Ivanov' 'Peter G Jones' 'Hartmut Kuhn' 'Sun-Chol Yu' # Attachment '3c.cif' data_3c _database_code_depnum_ccdc_archive 'CCDC 740213' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 N O4 Se' _chemical_formula_weight 248.10 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 4.9234(2) _cell_length_b 9.5712(2) _cell_length_c 17.3190(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 816.12(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9455 _cell_measurement_theta_min 2.1221 _cell_measurement_theta_max 30.7361 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.019 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 4.580 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92799 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18703 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2338 _reflns_number_gt 2059 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0156P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(8) _refine_ls_number_reflns 2338 _refine_ls_number_parameters 134 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0351 _refine_ls_wR_factor_gt 0.0348 _refine_ls_goodness_of_fit_ref 0.934 _refine_ls_restrained_S_all 0.933 _refine_ls_shift/su_max 0.016 _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 Se Se 0.60723(4) 0.62653(2) 0.924863(11) 0.01350(5) Uani 1 1 d . . . O1 O 0.2982(3) 0.68375(14) 0.90340(8) 0.0207(3) Uani 1 1 d . . . O2 O 0.5980(3) 0.59634(15) 1.02484(8) 0.0213(3) Uani 1 1 d D . . H02 H 0.683(5) 0.650(2) 1.0420(16) 0.060(11) Uiso 1 1 d D . . O3 O 0.1664(3) 0.07701(13) 0.74406(9) 0.0203(4) Uani 1 1 d . . . O4 O 0.5523(3) 0.01948(15) 0.83564(10) 0.0207(4) Uani 1 1 d D . . H04 H 0.442(4) 0.014(2) 0.8082(13) 0.017(7) Uiso 1 1 d D . . N N 0.0112(4) 0.29347(18) 0.72796(11) 0.0155(4) Uani 1 1 d D . . H1A H 0.023(4) 0.3811(18) 0.7362(12) 0.016(5) Uiso 1 1 d D . . H1B H -0.095(4) 0.260(2) 0.6933(12) 0.024(6) Uiso 1 1 d D . . C1 C 0.5741(4) 0.4316(2) 0.90014(11) 0.0138(4) Uani 1 1 d . . . C2 C 0.3816(4) 0.39163(19) 0.84611(10) 0.0118(4) Uani 1 1 d . . . H2 H 0.2601 0.4589 0.8253 0.014 Uiso 1 1 calc R . . C3 C 0.3663(4) 0.25218(18) 0.82225(11) 0.0112(4) Uani 1 1 d . . . C4 C 0.5505(4) 0.15463(19) 0.85544(12) 0.0144(4) Uani 1 1 d . . . C5 C 0.7401(4) 0.1979(2) 0.91049(11) 0.0170(5) Uani 1 1 d . . . H5 H 0.8598 0.1317 0.9331 0.020 Uiso 1 1 calc R . . C6 C 0.7542(4) 0.33625(19) 0.93215(12) 0.0162(4) Uani 1 1 d . . . H6 H 0.8860 0.3661 0.9687 0.019 Uiso 1 1 calc R . . C7 C 0.1739(4) 0.20363(19) 0.76284(12) 0.0116(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 Se 0.01620(8) 0.01272(8) 0.01156(8) -0.00165(9) -0.00097(9) -0.00217(10) O1 0.0231(7) 0.0168(7) 0.0222(9) -0.0060(6) -0.0069(6) 0.0052(6) O2 0.0302(8) 0.0210(8) 0.0126(7) -0.0020(6) -0.0018(8) -0.0082(8) O3 0.0228(9) 0.0108(7) 0.0271(9) -0.0044(6) -0.0042(7) 0.0008(6) O4 0.0236(10) 0.0134(7) 0.0251(9) -0.0012(6) -0.0035(8) 0.0038(7) N 0.0177(9) 0.0102(9) 0.0186(10) -0.0040(8) -0.0052(7) -0.0020(7) C1 0.0157(11) 0.0133(9) 0.0123(9) -0.0007(7) 0.0031(8) 0.0013(9) C2 0.0104(8) 0.0130(9) 0.0121(8) 0.0020(7) 0.0005(8) 0.0002(9) C3 0.0106(9) 0.0129(9) 0.0100(9) -0.0018(7) 0.0040(9) 0.0001(8) C4 0.0169(10) 0.0112(11) 0.0151(10) 0.0011(7) 0.0052(7) 0.0020(8) C5 0.0163(10) 0.0191(10) 0.0156(12) 0.0046(8) 0.0013(9) 0.0052(8) C6 0.0128(9) 0.0243(11) 0.0116(10) -0.0017(9) 0.0002(9) 0.0002(8) C7 0.0134(11) 0.0102(9) 0.0110(10) -0.0011(8) 0.0044(8) -0.0027(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 Se O1 1.6594(14) . ? Se O2 1.7560(14) . ? Se C1 1.9210(19) . ? O3 C7 1.255(2) . ? O4 C4 1.338(2) . ? N C7 1.321(3) . ? C1 C2 1.386(3) . ? C1 C6 1.388(3) . ? C2 C3 1.399(2) . ? C3 C4 1.423(3) . ? C3 C7 1.474(3) . ? C4 C5 1.397(3) . ? C5 C6 1.378(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Se O2 104.56(8) . . ? O1 Se C1 101.11(8) . . ? O2 Se C1 93.31(7) . . ? C2 C1 C6 121.67(18) . . ? C2 C1 Se 118.47(14) . . ? C6 C1 Se 119.69(15) . . ? C1 C2 C3 119.98(18) . . ? C2 C3 C4 118.19(18) . . ? C2 C3 C7 122.79(18) . . ? C4 C3 C7 119.00(16) . . ? O4 C4 C5 117.19(17) . . ? O4 C4 C3 122.35(18) . . ? C5 C4 C3 120.46(17) . . ? C6 C5 C4 120.29(18) . . ? C5 C6 C1 119.40(18) . . ? O3 C7 N 119.46(19) . . ? O3 C7 C3 120.29(18) . . ? N C7 C3 120.24(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Se C1 C2 25.40(17) . . . . ? O2 Se C1 C2 130.94(16) . . . . ? O1 Se C1 C6 -159.19(16) . . . . ? O2 Se C1 C6 -53.65(16) . . . . ? C6 C1 C2 C3 -0.3(3) . . . . ? Se C1 C2 C3 174.99(14) . . . . ? C1 C2 C3 C4 0.6(3) . . . . ? C1 C2 C3 C7 -177.54(17) . . . . ? C2 C3 C4 O4 -179.40(17) . . . . ? C7 C3 C4 O4 -1.2(3) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? C7 C3 C4 C5 178.39(17) . . . . ? O4 C4 C5 C6 178.36(18) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C4 C5 C6 C1 1.5(3) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? Se C1 C6 C5 -176.00(15) . . . . ? C2 C3 C7 O3 -179.25(19) . . . . ? C4 C3 C7 O3 2.7(3) . . . . ? C2 C3 C7 N 1.9(3) . . . . ? C4 C3 C7 N -176.19(18) . . . . ? 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 O2 H02 Se 0.73(2) 3.04(2) 3.7525(16) 166(3) 4_567 O2 H02 O1 0.73(2) 1.93(2) 2.636(2) 162(3) 4_567 N H1A O3 0.853(17) 2.122(18) 2.892(2) 150.1(18) 3_556 N H1B O1 0.858(17) 2.083(18) 2.932(2) 170(2) 3_546 C2 H2 O3 0.95 2.67 3.587(2) 162.4 3_556 C5 H5 O2 0.95 2.58 3.506(2) 164.1 4_557 O4 H04 O3 0.722(19) 1.86(2) 2.536(2) 157(2) . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.561 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.067 # Attachment '3d.cif' data_3d _database_code_depnum_ccdc_archive 'CCDC 740214' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 O5 Se' _chemical_formula_weight 277.13 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 11.9653(4) _cell_length_b 5.1029(2) _cell_length_c 17.4167(8) _cell_angle_alpha 90.00 _cell_angle_beta 110.947(4) _cell_angle_gamma 90.00 _cell_volume 993.14(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9890 _cell_measurement_theta_min 2.4987 _cell_measurement_theta_max 30.7571 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.853 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 3.779 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78098 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1419 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22715 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 29.11 _reflns_number_total 2658 _reflns_number_gt 2112 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0247P)^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 'rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2658 _refine_ls_number_parameters 154 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0208 _refine_ls_wR_factor_ref 0.0463 _refine_ls_wR_factor_gt 0.0456 _refine_ls_goodness_of_fit_ref 0.928 _refine_ls_restrained_S_all 0.927 _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 Se Se 0.126900(15) 0.60107(3) 0.247033(11) 0.01448(6) Uani 1 1 d . . . O1 O 0.04849(11) 0.5568(2) 0.30808(7) 0.0186(3) Uani 1 1 d . . . O2 O 0.04095(12) 0.4651(3) 0.15242(8) 0.0195(3) Uani 1 1 d D . . H02 H 0.013(2) 0.344(4) 0.1601(15) 0.038(8) Uiso 1 1 d D . . O4 O 0.41205(13) -0.3193(3) 0.49810(8) 0.0301(3) Uani 1 1 d . . . O5 O 0.50103(12) -0.2479(3) 0.38015(9) 0.0255(3) Uani 1 1 d D . . H05 H 0.501(2) -0.297(5) 0.4198(12) 0.037(8) Uiso 1 1 d D . . C1 C 0.24120(15) 0.3201(3) 0.28824(11) 0.0147(4) Uani 1 1 d . . . C2 C 0.24383(15) 0.1831(3) 0.35729(11) 0.0159(4) Uani 1 1 d . . . H2 H 0.1874 0.2217 0.3826 0.019 Uiso 1 1 calc R . . C3 C 0.32990(15) -0.0130(4) 0.39002(11) 0.0158(4) Uani 1 1 d . . . C4 C 0.41344(15) -0.0668(3) 0.35219(11) 0.0176(4) Uani 1 1 d . . . C5 C 0.40670(16) 0.0681(4) 0.28080(12) 0.0198(4) Uani 1 1 d . . . H5 H 0.4606 0.0265 0.2536 0.024 Uiso 1 1 calc R . . C6 C 0.32206(15) 0.2615(4) 0.24977(11) 0.0174(4) Uani 1 1 d . . . H6 H 0.3189 0.3552 0.2019 0.021 Uiso 1 1 calc R . . C7 C 0.33380(17) -0.1624(4) 0.46370(11) 0.0216(4) Uani 1 1 d . A . O3 O 0.24293(12) -0.1064(3) 0.48761(8) 0.0315(3) Uani 1 1 d D . . C8 C 0.2331(3) -0.2310(7) 0.56032(16) 0.0288(8) Uani 0.812(7) 1 d PDU A 1 H8A H 0.1829 -0.1223 0.5823 0.035 Uiso 0.812(7) 1 calc PR A 1 H8B H 0.3134 -0.2482 0.6035 0.035 Uiso 0.812(7) 1 calc PR A 1 C9 C 0.1779(4) -0.4956(7) 0.53721(17) 0.0397(10) Uani 0.812(7) 1 d PDU A 1 H9A H 0.1047 -0.4803 0.4886 0.060 Uiso 0.812(7) 1 calc PR A 1 H9B H 0.1585 -0.5683 0.5830 0.060 Uiso 0.812(7) 1 calc PR A 1 H9C H 0.2345 -0.6119 0.5248 0.060 Uiso 0.812(7) 1 calc PR A 1 C8' C 0.2459(10) -0.326(3) 0.5477(8) 0.022(3) Uiso 0.188(7) 1 d PDU A 2 H8'1 H 0.2884 -0.4805 0.5374 0.026 Uiso 0.188(7) 1 calc PR A 2 H8'2 H 0.2875 -0.2668 0.6050 0.026 Uiso 0.188(7) 1 calc PR A 2 C9' C 0.1192(11) -0.392(3) 0.5338(7) 0.030(3) Uiso 0.188(7) 1 d PDU A 2 H9'1 H 0.1164 -0.5477 0.5661 0.046 Uiso 0.188(7) 1 calc PR A 2 H9'2 H 0.0766 -0.4279 0.4753 0.046 Uiso 0.188(7) 1 calc PR A 2 H9'3 H 0.0812 -0.2446 0.5509 0.046 Uiso 0.188(7) 1 calc PR A 2 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 Se 0.01563(9) 0.01189(9) 0.01573(9) 0.00091(8) 0.00538(6) -0.00009(8) O1 0.0222(7) 0.0180(7) 0.0183(7) 0.0025(5) 0.0103(5) 0.0032(5) O2 0.0222(7) 0.0186(8) 0.0168(7) 0.0009(6) 0.0058(6) -0.0032(6) O4 0.0402(8) 0.0240(8) 0.0205(7) 0.0055(6) 0.0039(7) 0.0117(7) O5 0.0236(7) 0.0238(8) 0.0266(9) 0.0041(7) 0.0059(7) 0.0103(6) C1 0.0133(8) 0.0114(9) 0.0170(9) 0.0005(7) 0.0028(7) -0.0002(7) C2 0.0151(8) 0.0153(9) 0.0160(9) -0.0028(7) 0.0041(7) -0.0013(7) C3 0.0175(9) 0.0132(9) 0.0135(9) 0.0003(7) 0.0016(7) -0.0012(7) C4 0.0143(8) 0.0118(9) 0.0222(9) -0.0028(7) 0.0012(7) 0.0016(7) C5 0.0174(9) 0.0189(10) 0.0255(10) -0.0011(8) 0.0104(7) 0.0013(8) C6 0.0167(9) 0.0170(10) 0.0192(9) 0.0031(7) 0.0071(7) -0.0027(8) C7 0.0269(10) 0.0180(11) 0.0154(9) -0.0019(8) 0.0023(8) -0.0008(8) O3 0.0309(8) 0.0440(10) 0.0213(7) 0.0149(7) 0.0113(6) 0.0047(7) C8 0.0465(18) 0.0300(18) 0.0157(14) 0.0064(12) 0.0182(12) 0.0127(14) C9 0.052(2) 0.0457(19) 0.0248(15) 0.0097(14) 0.0178(14) -0.0032(18) _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 Se O1 1.6659(11) . ? Se O2 1.7442(13) . ? Se C1 1.9339(17) . ? O4 C7 1.215(2) . ? O5 C4 1.351(2) . ? C1 C2 1.381(2) . ? C1 C6 1.392(2) . ? C2 C3 1.403(2) . ? C3 C4 1.407(2) . ? C3 C7 1.479(3) . ? C4 C5 1.398(3) . ? C5 C6 1.378(2) . ? C7 O3 1.327(2) . ? O3 C8 1.459(3) . ? O3 C8' 1.524(11) . ? C8 C9 1.494(4) . ? C8' C9' 1.486(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Se O2 105.82(6) . . ? O1 Se C1 98.48(7) . . ? O2 Se C1 98.95(7) . . ? C2 C1 C6 120.46(16) . . ? C2 C1 Se 119.42(13) . . ? C6 C1 Se 120.10(13) . . ? C1 C2 C3 119.97(16) . . ? C2 C3 C4 119.36(16) . . ? C2 C3 C7 120.74(16) . . ? C4 C3 C7 119.91(16) . . ? O5 C4 C5 116.63(17) . . ? O5 C4 C3 123.65(17) . . ? C5 C4 C3 119.72(16) . . ? C6 C5 C4 120.13(17) . . ? C5 C6 C1 120.30(17) . . ? O4 C7 O3 124.10(18) . . ? O4 C7 C3 123.18(18) . . ? O3 C7 C3 112.72(16) . . ? C7 O3 C8 120.53(19) . . ? C7 O3 C8' 103.7(5) . . ? C8 O3 C8' 22.1(5) . . ? O3 C8 C9 109.0(2) . . ? C9' C8' O3 106.5(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Se C1 C2 -7.63(15) . . . . ? O2 Se C1 C2 -115.24(14) . . . . ? O1 Se C1 C6 174.04(14) . . . . ? O2 Se C1 C6 66.43(15) . . . . ? C6 C1 C2 C3 1.3(3) . . . . ? Se C1 C2 C3 -177.06(13) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C1 C2 C3 C7 -179.76(16) . . . . ? C2 C3 C4 O5 178.60(17) . . . . ? C7 C3 C4 O5 -1.2(3) . . . . ? C2 C3 C4 C5 -2.5(3) . . . . ? C7 C3 C4 C5 177.65(17) . . . . ? O5 C4 C5 C6 -178.06(16) . . . . ? C3 C4 C5 C6 3.0(3) . . . . ? C4 C5 C6 C1 -1.3(3) . . . . ? C2 C1 C6 C5 -0.8(3) . . . . ? Se C1 C6 C5 177.49(14) . . . . ? C2 C3 C7 O4 -174.05(18) . . . . ? C4 C3 C7 O4 5.8(3) . . . . ? C2 C3 C7 O3 6.1(2) . . . . ? C4 C3 C7 O3 -174.12(16) . . . . ? O4 C7 O3 C8 1.4(3) . . . . ? C3 C7 O3 C8 -178.7(2) . . . . ? O4 C7 O3 C8' -14.1(6) . . . . ? C3 C7 O3 C8' 165.8(6) . . . . ? C7 O3 C8 C9 -82.1(3) . . . . ? C8' O3 C8 C9 -38.4(12) . . . . ? C7 O3 C8' C9' -142.1(10) . . . . ? C8 O3 C8' C9' 75.7(15) . . . . ? 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 O2 H02 Se 0.741(19) 2.98(2) 3.6147(14) 146(2) 2_545 O2 H02 O1 0.741(19) 1.810(19) 2.5470(18) 173(3) 2_545 O5 H05 O4 0.737(19) 2.43(2) 2.980(2) 133(2) 3_646 C8 H8A Se 0.99 3.17 3.948(3) 136.3 4_566 C8 H8A O2 0.99 2.55 3.512(4) 164.1 4_566 C9 H9C O3 0.98 2.62 3.398(4) 136.8 1_545 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.535 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.069 # Attachment '6.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 740215' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H8 O5 Se' _chemical_formula_weight 263.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 5.1610(2) _cell_length_b 17.4964(8) _cell_length_c 10.2112(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.578(4) _cell_angle_gamma 90.00 _cell_volume 922.01(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 13796 _cell_measurement_theta_min 4.3267 _cell_measurement_theta_max 75.7909 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.895 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 5.529 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.70130 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Nova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Atlas, Nova' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3543 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16694 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.02 _diffrn_reflns_theta_max 75.86 _reflns_number_total 1898 _reflns_number_gt 1875 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.40 (release 27-04-2009 CrysAlis171 .NET) (compiled Apr 27 2009,10:20:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker XP' _computing_publication_material SHELXL-97 _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^)+(0.0312P)^2^+1.0329P] 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 'rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1898 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0621 _refine_ls_wR_factor_gt 0.0620 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.114 _refine_ls_shift/su_max 0.003 _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 Se Se 0.44982(4) 0.539244(10) 0.832383(19) 0.01527(9) Uani 1 1 d . . . O1 O 0.6465(3) 0.46978(8) 0.88413(14) 0.0181(3) Uani 1 1 d . . . O2 O 0.4943(3) 0.54290(8) 0.66050(14) 0.0211(3) Uani 1 1 d . . . O3 O 0.4604(3) 0.83723(8) 0.71184(15) 0.0218(3) Uani 1 1 d . . . H03 H 0.436(7) 0.881(2) 0.679(4) 0.051(10) Uiso 1 1 d . . . O4 O 0.8169(3) 0.89238(8) 0.79402(15) 0.0204(3) Uani 1 1 d . . . O5 O 1.1038(3) 0.81623(9) 0.95993(15) 0.0226(3) Uani 1 1 d . . . H05 H 1.055(6) 0.8519(18) 0.919(3) 0.033(8) Uiso 1 1 d . . . C1 C 0.6547(4) 0.62793(11) 0.87577(19) 0.0162(4) Uani 1 1 d . . . C2 C 0.5906(4) 0.69654(11) 0.81675(19) 0.0168(4) Uani 1 1 d . . . H2 H 0.4464 0.6993 0.7584 0.020 Uiso 1 1 calc R . . C3 C 0.7381(4) 0.76176(11) 0.84290(19) 0.0165(4) Uani 1 1 d . . . C4 C 0.9507(4) 0.75638(11) 0.93024(19) 0.0173(4) Uani 1 1 d . . . C5 C 1.0078(4) 0.68677(11) 0.9912(2) 0.0193(4) Uani 1 1 d . . . H5 H 1.1478 0.6838 1.0521 0.023 Uiso 1 1 calc R . . C6 C 0.8629(4) 0.62238(11) 0.96380(19) 0.0173(4) Uani 1 1 d . . . H6 H 0.9040 0.5749 1.0042 0.021 Uiso 1 1 calc R . . C7 C 0.6769(4) 0.83625(11) 0.78074(19) 0.0168(4) Uani 1 1 d . . . C8 C 0.7601(5) 0.54140(13) 0.6152(2) 0.0266(5) Uani 1 1 d . . . H8A H 0.8400 0.5916 0.6297 0.040 Uiso 1 1 calc R . . H8B H 0.7620 0.5292 0.5216 0.040 Uiso 1 1 calc R . . H8C H 0.8577 0.5024 0.6639 0.040 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 Se 0.01804(14) 0.01043(13) 0.01728(14) 0.00034(6) -0.00227(9) -0.00016(7) O1 0.0228(7) 0.0127(6) 0.0187(7) 0.0001(5) -0.0048(6) 0.0020(5) O2 0.0255(7) 0.0201(8) 0.0177(7) 0.0011(5) -0.0045(6) -0.0033(5) O3 0.0258(8) 0.0135(7) 0.0260(8) 0.0048(6) -0.0109(6) -0.0018(6) O4 0.0227(7) 0.0131(6) 0.0251(7) 0.0010(5) -0.0040(6) -0.0022(5) O5 0.0231(7) 0.0164(7) 0.0280(8) 0.0011(6) -0.0079(6) -0.0038(6) C1 0.0186(9) 0.0117(8) 0.0184(9) -0.0018(7) 0.0000(7) -0.0011(7) C2 0.0181(9) 0.0149(9) 0.0174(9) -0.0009(7) -0.0020(7) -0.0002(7) C3 0.0190(9) 0.0134(9) 0.0170(9) 0.0006(7) -0.0005(7) 0.0013(7) C4 0.0185(9) 0.0144(9) 0.0189(9) -0.0030(7) -0.0002(7) -0.0011(7) C5 0.0193(9) 0.0189(9) 0.0197(10) -0.0005(8) -0.0054(7) 0.0007(8) C6 0.0212(9) 0.0136(9) 0.0170(9) 0.0021(7) 0.0005(7) 0.0018(7) C7 0.0201(9) 0.0140(9) 0.0164(9) -0.0002(7) -0.0013(7) -0.0005(7) C8 0.0322(12) 0.0278(12) 0.0197(11) -0.0018(8) 0.0033(9) -0.0026(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se O1 1.6662(14) . ? Se O2 1.7735(15) . ? Se C1 1.9268(19) . ? O2 C8 1.452(3) . ? O3 C7 1.314(2) . ? O4 C7 1.226(2) . ? O5 C4 1.345(2) . ? C1 C2 1.382(3) . ? C1 C6 1.397(3) . ? C2 C3 1.396(3) . ? C3 C4 1.410(3) . ? C3 C7 1.482(3) . ? C4 C5 1.398(3) . ? C5 C6 1.379(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Se O2 104.81(7) . . ? O1 Se C1 100.56(8) . . ? O2 Se C1 97.03(8) . . ? C8 O2 Se 116.51(14) . . ? C2 C1 C6 121.33(18) . . ? C2 C1 Se 118.10(15) . . ? C6 C1 Se 120.57(14) . . ? C1 C2 C3 119.94(18) . . ? C2 C3 C4 119.06(18) . . ? C2 C3 C7 121.57(18) . . ? C4 C3 C7 119.37(18) . . ? O5 C4 C5 117.22(18) . . ? O5 C4 C3 122.84(18) . . ? C5 C4 C3 119.94(18) . . ? C6 C5 C4 120.65(18) . . ? C5 C6 C1 119.05(18) . . ? O4 C7 O3 123.07(18) . . ? O4 C7 C3 122.30(18) . . ? O3 C7 C3 114.63(17) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Se O2 C8 -46.01(14) . . . . ? C1 Se O2 C8 56.91(14) . . . . ? O1 Se C1 C2 162.70(15) . . . . ? O2 Se C1 C2 56.14(16) . . . . ? O1 Se C1 C6 -16.85(17) . . . . ? O2 Se C1 C6 -123.41(16) . . . . ? C6 C1 C2 C3 1.2(3) . . . . ? Se C1 C2 C3 -178.38(15) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C1 C2 C3 C7 179.50(18) . . . . ? C2 C3 C4 O5 179.45(18) . . . . ? C7 C3 C4 O5 -0.3(3) . . . . ? C2 C3 C4 C5 -1.3(3) . . . . ? C7 C3 C4 C5 178.92(18) . . . . ? O5 C4 C5 C6 -178.69(18) . . . . ? C3 C4 C5 C6 2.0(3) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? C2 C1 C6 C5 -0.5(3) . . . . ? Se C1 C6 C5 179.06(15) . . . . ? C2 C3 C7 O4 -173.72(19) . . . . ? C4 C3 C7 O4 6.0(3) . . . . ? C2 C3 C7 O3 6.9(3) . . . . ? C4 C3 C7 O3 -173.32(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 C5 H5 O3 0.95 2.31 3.256(2) 172.4 4_676 C6 H6 Se 0.95 3.19 3.8731(19) 130.4 3_667 O3 H03 Se 0.84(4) 2.83(4) 3.5939(15) 151(3) 2_656 O3 H03 O1 0.84(4) 1.73(4) 2.575(2) 174(4) 2_656 C8 H8B O2 0.98 2.60 3.428(3) 142.6 3_666 C8 H8C O4 0.98 2.59 3.519(3) 158.6 2_746 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 72.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.381 _refine_diff_density_min -0.568 _refine_diff_density_rms 0.089