# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Poupon Erwan' _publ_contact_author_email ERWAN.POUPON@U-PSUD.FR _publ_section_title ; Biomimetically relevant self-condensations of C5 units derived from lysine ; loop_ _publ_author_name 'Poupon Erwan' 'Edmond Gravel' 'Pascal Retailleau' 'Rim Salame' # Attachment 'cif_B926786G.cif' data_compound_8_CCDC_753047 _database_code_depnum_ccdc_archive 'CCDC 753047' #TrackingRef 'cif_B926786G.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-oxo-3,4,4a,7,8,8a-hexahydro-2H-chromene-6-carbaldehyde ; _chemical_name_common 2-oxo-3,4,4a,7,8,8a-hexahydro-2H-chromene-6-carbaldehyde _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 O3' _chemical_formula_sum 'C10 H12 O3' _chemical_formula_weight 180.20 _chemical_absolute_configuration ? 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.6270(10) _cell_length_b 13.282(3) _cell_length_c 10.388(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.38(5) _cell_angle_gamma 90.00 _cell_volume 908.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1727 _cell_measurement_theta_min 0.41 _cell_measurement_theta_max 25.35 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.47 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 0.967 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13337 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.35 _reflns_number_total 1646 _reflns_number_gt 1166 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.1220P)^2^+0.1931P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.20(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1646 _refine_ls_number_parameters 119 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2177 _refine_ls_wR_factor_gt 0.1952 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.077 _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 O1 O 0.4939(3) 0.12755(16) 0.11859(17) 0.0817(7) Uani 1 1 d . . . O2 O 0.2231(3) 0.2204(2) 0.0845(2) 0.1181(10) Uani 1 1 d . . . O3 O 1.3309(3) -0.05470(19) 0.3913(2) 0.1007(8) Uani 1 1 d . . . C1 C 1.0515(3) 0.05070(18) 0.3264(2) 0.0593(7) Uani 1 1 d . . . C2 C 0.9728(4) -0.0150(2) 0.2158(3) 0.0752(8) Uani 1 1 d . . . H2A H 0.9240 -0.0775 0.2496 0.090 Uiso 1 1 calc R . . H2B H 1.0836 -0.0314 0.1657 0.090 Uiso 1 1 calc R . . C3 C 0.8040(5) 0.0324(2) 0.1276(3) 0.0854(9) Uani 1 1 d . . . H3A H 0.8612 0.0746 0.0646 0.102 Uiso 1 1 calc R . . H3B H 0.7238 -0.0198 0.0810 0.102 Uiso 1 1 calc R . . C4 C 0.6710(3) 0.09438(19) 0.2030(2) 0.0664(7) Uani 1 1 d . . . H4 H 0.6207 0.0490 0.2667 0.080 Uiso 1 1 calc R . . C5 C 0.7757(4) 0.17703(19) 0.2772(2) 0.0681(8) Uani 1 1 d . . . H5 H 0.8209 0.2245 0.2141 0.082 Uiso 1 1 calc R . . C6 C 0.9626(3) 0.1367(2) 0.3541(2) 0.0669(7) Uani 1 1 d . . . H6 H 1.0196 0.1736 0.4251 0.080 Uiso 1 1 calc R . . C7 C 0.6348(4) 0.2335(2) 0.3544(3) 0.0837(9) Uani 1 1 d . . . H7A H 0.7039 0.2921 0.3938 0.100 Uiso 1 1 calc R . . H7B H 0.5957 0.1907 0.4231 0.100 Uiso 1 1 calc R . . C8 C 0.4475(4) 0.2665(2) 0.2685(3) 0.0887(10) Uani 1 1 d . . . H8A H 0.3364 0.2704 0.3217 0.106 Uiso 1 1 calc R . . H8B H 0.4715 0.3342 0.2385 0.106 Uiso 1 1 calc R . . C9 C 0.3789(4) 0.2041(2) 0.1534(3) 0.0816(9) Uani 1 1 d . . . C10 C 1.2338(4) 0.0200(2) 0.4084(2) 0.0736(8) Uani 1 1 d . . . H10 H 1.2784 0.0608 0.4786 0.088 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0664(11) 0.1043(15) 0.0688(11) 0.0059(9) -0.0173(8) 0.0022(10) O2 0.0754(13) 0.169(2) 0.1059(17) 0.0551(16) -0.0094(11) 0.0231(14) O3 0.0701(13) 0.1282(18) 0.1039(17) 0.0173(13) 0.0101(11) 0.0292(12) C1 0.0516(12) 0.0737(15) 0.0530(12) 0.0045(10) 0.0072(9) -0.0021(10) C2 0.0739(16) 0.0779(16) 0.0727(16) -0.0144(13) 0.0027(12) 0.0091(13) C3 0.094(2) 0.095(2) 0.0619(15) -0.0217(13) -0.0122(14) 0.0086(16) C4 0.0567(13) 0.0823(16) 0.0569(12) -0.0035(11) -0.0081(10) -0.0013(12) C5 0.0679(15) 0.0703(15) 0.0645(14) -0.0057(11) -0.0005(11) 0.0013(11) C6 0.0594(13) 0.0820(17) 0.0569(13) -0.0091(11) -0.0041(10) -0.0085(12) C7 0.0891(19) 0.0882(18) 0.0736(17) -0.0095(14) 0.0076(14) 0.0155(15) C8 0.0773(18) 0.0839(18) 0.108(2) 0.0204(17) 0.0236(16) 0.0202(15) C9 0.0640(16) 0.102(2) 0.0781(17) 0.0367(15) 0.0055(13) 0.0070(15) C10 0.0509(13) 0.103(2) 0.0674(15) 0.0146(14) 0.0095(11) -0.0025(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.343(4) . ? O1 C4 1.453(3) . ? O2 C9 1.209(3) . ? O3 C10 1.207(3) . ? C1 C6 1.331(3) . ? C1 C10 1.457(3) . ? C1 C2 1.491(3) . ? C2 C3 1.503(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.490(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.470(3) . ? C4 H4 0.9800 . ? C5 C6 1.497(3) . ? C5 C7 1.498(4) . ? C5 H5 0.9800 . ? C6 H6 0.9300 . ? C7 C8 1.511(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.485(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C10 H10 0.9300 . ? 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 C9 O1 C4 120.8(2) . . ? C6 C1 C10 118.1(2) . . ? C6 C1 C2 123.0(2) . . ? C10 C1 C2 118.9(2) . . ? C1 C2 C3 113.4(2) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C4 C3 C2 110.8(2) . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? O1 C4 C5 113.1(2) . . ? O1 C4 C3 109.62(19) . . ? C5 C4 C3 114.5(2) . . ? O1 C4 H4 106.3 . . ? C5 C4 H4 106.3 . . ? C3 C4 H4 106.3 . . ? C4 C5 C6 109.1(2) . . ? C4 C5 C7 111.6(2) . . ? C6 C5 C7 114.9(2) . . ? C4 C5 H5 106.9 . . ? C6 C5 H5 106.9 . . ? C7 C5 H5 106.9 . . ? C1 C6 C5 123.5(2) . . ? C1 C6 H6 118.3 . . ? C5 C6 H6 118.3 . . ? C5 C7 C8 110.4(2) . . ? C5 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? C5 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C9 C8 C7 118.1(2) . . ? C9 C8 H8A 107.8 . . ? C7 C8 H8A 107.8 . . ? C9 C8 H8B 107.8 . . ? C7 C8 H8B 107.8 . . ? H8A C8 H8B 107.1 . . ? O2 C9 O1 116.7(3) . . ? O2 C9 C8 122.7(3) . . ? O1 C9 C8 120.5(2) . . ? O3 C10 C1 124.4(3) . . ? O3 C10 H10 117.8 . . ? C1 C10 H10 117.8 . . ? 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 C6 C1 C2 C3 8.7(4) . . . . ? C10 C1 C2 C3 -171.3(2) . . . . ? C1 C2 C3 C4 -36.2(3) . . . . ? C9 O1 C4 C5 -33.7(3) . . . . ? C9 O1 C4 C3 -162.9(2) . . . . ? C2 C3 C4 O1 -172.0(2) . . . . ? C2 C3 C4 C5 59.7(3) . . . . ? O1 C4 C5 C6 -176.33(19) . . . . ? C3 C4 C5 C6 -49.7(3) . . . . ? O1 C4 C5 C7 55.6(3) . . . . ? C3 C4 C5 C7 -177.8(2) . . . . ? C10 C1 C6 C5 179.5(2) . . . . ? C2 C1 C6 C5 -0.4(4) . . . . ? C4 C5 C6 C1 20.2(3) . . . . ? C7 C5 C6 C1 146.4(3) . . . . ? C4 C5 C7 C8 -52.5(3) . . . . ? C6 C5 C7 C8 -177.4(2) . . . . ? C5 C7 C8 C9 29.0(4) . . . . ? C4 O1 C9 O2 -172.6(2) . . . . ? C4 O1 C9 C8 9.5(4) . . . . ? C7 C8 C9 O2 174.6(3) . . . . ? C7 C8 C9 O1 -7.7(4) . . . . ? C6 C1 C10 O3 -178.0(2) . . . . ? C2 C1 C10 O3 2.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.332 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.130 #===END data_compound_10_CCDC_753048 _database_code_depnum_ccdc_archive 'CCDC 753048' #TrackingRef '3Structures_OrgBiomolChem.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 O4' _chemical_formula_sum 'C10 H16 O4' _chemical_formula_weight 200.23 _chemical_absolute_configuration . 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.280(3) _cell_length_b 7.095(3) _cell_length_c 11.413(5) _cell_angle_alpha 97.531(5) _cell_angle_beta 102.847(8) _cell_angle_gamma 101.348(6) _cell_volume 477.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 970 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 21.491 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 216 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2432 _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_sigmaI/netI 0.0535 _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 1.86 _diffrn_reflns_theta_max 21.59 _reflns_number_total 1098 _reflns_number_gt 817 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.1014P)^2^+0.6689P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1098 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.2053 _refine_ls_wR_factor_gt 0.1837 _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 0.1656(6) 0.3065(6) 0.7233(4) 0.0364(11) Uani 1 1 d . . . O2 O 0.3793(5) 0.1939(5) 0.5858(3) 0.0583(10) Uani 1 1 d . . . H2 H 0.5133 0.2149 0.6200 0.087 Uiso 1 1 calc R . . O3 O -0.0552(5) 0.4376(5) 0.8502(3) 0.0619(11) Uani 1 1 d . . . C4 C 0.3127(7) 0.2590(7) 0.8385(4) 0.0474(13) Uani 1 1 d . . . H4A H 0.3625 0.1412 0.8169 0.057 Uiso 1 1 calc R . . H4B H 0.4442 0.3655 0.8733 0.057 Uiso 1 1 calc R . . O4 O -0.1510(6) 0.1037(6) 0.7676(3) 0.0909(15) Uani 1 1 d . . . O1 O -0.1784(6) 0.1512(5) 0.5739(4) 0.0740(12) Uani 1 1 d . . . H1 H -0.2432 0.0443 0.5311 0.111 Uiso 1 1 calc R . . C7 C 0.0679(7) 0.4803(6) 0.7612(4) 0.0455(12) Uani 1 1 d . . . H7 H -0.0381 0.4978 0.6886 0.055 Uiso 1 1 calc R . . C8 C 0.2911(7) 0.3531(6) 0.6281(4) 0.0442(12) Uani 1 1 d . . . H8 H 0.1809 0.3719 0.5576 0.053 Uiso 1 1 calc R . . C9 C 0.2456(8) 0.6696(7) 0.8083(5) 0.0561(14) Uani 1 1 d . . . H9A H 0.1755 0.7757 0.8279 0.067 Uiso 1 1 calc R . . H9B H 0.3503 0.6587 0.8823 0.067 Uiso 1 1 calc R . . C10 C 0.4703(8) 0.5443(7) 0.6712(5) 0.0531(13) Uani 1 1 d . . . H10A H 0.5380 0.5734 0.6051 0.064 Uiso 1 1 calc R . . H10B H 0.5873 0.5299 0.7386 0.064 Uiso 1 1 calc R . . C11 C -0.0599(8) 0.2473(8) 0.8750(5) 0.0612(15) Uani 1 1 d . . . H11 H -0.1525 0.2228 0.9326 0.073 Uiso 1 1 calc R . . C12 C -0.0321(8) 0.1260(8) 0.6754(4) 0.0557(14) Uani 1 1 d . . . H12 H 0.0240 0.0091 0.6564 0.067 Uiso 1 1 calc R . . C13 C 0.1735(9) 0.2298(8) 0.9317(5) 0.0615(15) Uani 1 1 d . . . H13A H 0.1691 0.1017 0.9536 0.074 Uiso 1 1 calc R . . H13B H 0.2401 0.3280 1.0053 0.074 Uiso 1 1 calc R . . C14 C 0.3704(9) 0.7131(7) 0.7124(5) 0.0635(15) Uani 1 1 d . . . H14A H 0.4900 0.8300 0.7452 0.076 Uiso 1 1 calc R . . H14B H 0.2681 0.7386 0.6422 0.076 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 0.033(2) 0.036(3) 0.038(3) 0.003(2) 0.007(2) 0.0078(19) O2 0.0417(18) 0.063(2) 0.063(2) -0.0116(17) 0.0117(16) 0.0114(16) O3 0.060(2) 0.083(3) 0.059(2) 0.0227(19) 0.0276(18) 0.0350(19) C4 0.047(3) 0.039(3) 0.052(3) 0.005(2) 0.004(2) 0.010(2) O4 0.075(3) 0.100(3) 0.069(3) -0.021(2) 0.031(2) -0.039(2) O1 0.058(2) 0.071(3) 0.077(3) -0.006(2) -0.002(2) 0.012(2) C7 0.044(3) 0.049(3) 0.042(3) 0.005(2) 0.008(2) 0.015(2) C8 0.042(3) 0.047(3) 0.042(3) 0.003(2) 0.010(2) 0.011(2) C9 0.064(3) 0.038(3) 0.063(3) 0.000(2) 0.012(3) 0.016(2) C10 0.050(3) 0.054(3) 0.053(3) 0.010(2) 0.017(2) 0.002(2) C11 0.055(3) 0.069(4) 0.055(3) 0.009(3) 0.021(3) 0.000(3) C12 0.035(3) 0.076(4) 0.046(3) 0.005(3) 0.004(2) 0.001(2) C13 0.080(4) 0.057(3) 0.056(3) 0.022(3) 0.021(3) 0.024(3) C14 0.072(4) 0.043(3) 0.072(4) 0.013(3) 0.013(3) 0.011(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 C8 1.512(6) . ? C1 C7 1.536(6) . ? C1 C12 1.539(6) . ? C1 C4 1.547(6) . ? O2 C8 1.427(5) . ? O2 H2 0.8200 . ? O3 C11 1.412(6) . ? O3 C7 1.435(5) . ? C4 C13 1.529(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? O4 C11 1.414(6) . ? O4 C12 1.427(6) . ? O1 C12 1.365(6) . ? O1 H1 0.8200 . ? C7 C9 1.514(6) . ? C7 H7 0.9800 . ? C8 C10 1.525(6) . ? C8 H8 0.9800 . ? C9 C14 1.511(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C14 1.526(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C13 1.501(7) . ? C11 H11 0.9800 . ? C12 H12 0.9800 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? 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 C8 C1 C7 109.2(3) . . ? C8 C1 C12 112.5(4) . . ? C7 C1 C12 107.2(3) . . ? C8 C1 C4 113.5(3) . . ? C7 C1 C4 109.2(3) . . ? C12 C1 C4 104.9(4) . . ? C8 O2 H2 109.5 . . ? C11 O3 C7 112.0(3) . . ? C13 C4 C1 108.8(4) . . ? C13 C4 H4A 109.9 . . ? C1 C4 H4A 109.9 . . ? C13 C4 H4B 109.9 . . ? C1 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? C11 O4 C12 114.1(4) . . ? C12 O1 H1 109.5 . . ? O3 C7 C9 110.7(4) . . ? O3 C7 C1 110.1(3) . . ? C9 C7 C1 112.7(4) . . ? O3 C7 H7 107.7 . . ? C9 C7 H7 107.7 . . ? C1 C7 H7 107.7 . . ? O2 C8 C1 111.9(4) . . ? O2 C8 C10 112.3(4) . . ? C1 C8 C10 112.3(4) . . ? O2 C8 H8 106.6 . . ? C1 C8 H8 106.6 . . ? C10 C8 H8 106.6 . . ? C14 C9 C7 109.8(4) . . ? C14 C9 H9A 109.7 . . ? C7 C9 H9A 109.7 . . ? C14 C9 H9B 109.7 . . ? C7 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C8 C10 C14 111.2(4) . . ? C8 C10 H10A 109.4 . . ? C14 C10 H10A 109.4 . . ? C8 C10 H10B 109.4 . . ? C14 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O3 C11 O4 111.7(4) . . ? O3 C11 C13 110.1(4) . . ? O4 C11 C13 108.6(5) . . ? O3 C11 H11 108.8 . . ? O4 C11 H11 108.8 . . ? C13 C11 H11 108.8 . . ? O1 C12 O4 107.6(4) . . ? O1 C12 C1 110.8(4) . . ? O4 C12 C1 108.4(4) . . ? O1 C12 H12 110.0 . . ? O4 C12 H12 110.0 . . ? C1 C12 H12 110.0 . . ? C11 C13 C4 108.1(4) . . ? C11 C13 H13A 110.1 . . ? C4 C13 H13A 110.1 . . ? C11 C13 H13B 110.1 . . ? C4 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? C9 C14 C10 112.0(4) . . ? C9 C14 H14A 109.2 . . ? C10 C14 H14A 109.2 . . ? C9 C14 H14B 109.2 . . ? C10 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? 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 C8 C1 C4 C13 175.8(4) . . . . ? C7 C1 C4 C13 53.7(5) . . . . ? C12 C1 C4 C13 -61.0(4) . . . . ? C11 O3 C7 C9 -127.5(4) . . . . ? C11 O3 C7 C1 -2.2(5) . . . . ? C8 C1 C7 O3 179.0(3) . . . . ? C12 C1 C7 O3 56.9(4) . . . . ? C4 C1 C7 O3 -56.3(4) . . . . ? C8 C1 C7 C9 -56.8(5) . . . . ? C12 C1 C7 C9 -178.9(4) . . . . ? C4 C1 C7 C9 67.9(5) . . . . ? C7 C1 C8 O2 -177.9(3) . . . . ? C12 C1 C8 O2 -58.9(5) . . . . ? C4 C1 C8 O2 60.0(5) . . . . ? C7 C1 C8 C10 54.8(5) . . . . ? C12 C1 C8 C10 173.8(4) . . . . ? C4 C1 C8 C10 -67.3(5) . . . . ? O3 C7 C9 C14 -179.1(4) . . . . ? C1 C7 C9 C14 57.1(5) . . . . ? O2 C8 C10 C14 178.3(4) . . . . ? C1 C8 C10 C14 -54.6(5) . . . . ? C7 O3 C11 O4 -56.8(5) . . . . ? C7 O3 C11 C13 64.0(5) . . . . ? C12 O4 C11 O3 58.9(6) . . . . ? C12 O4 C11 C13 -62.7(6) . . . . ? C11 O4 C12 O1 -119.9(5) . . . . ? C11 O4 C12 C1 -0.1(6) . . . . ? C8 C1 C12 O1 -57.3(5) . . . . ? C7 C1 C12 O1 62.8(5) . . . . ? C4 C1 C12 O1 178.8(4) . . . . ? C8 C1 C12 O4 -175.1(4) . . . . ? C7 C1 C12 O4 -55.0(5) . . . . ? C4 C1 C12 O4 61.0(5) . . . . ? O3 C11 C13 C4 -63.4(5) . . . . ? O4 C11 C13 C4 59.1(5) . . . . ? C1 C4 C13 C11 3.0(5) . . . . ? C7 C9 C14 C10 -55.3(5) . . . . ? C8 C10 C14 C9 54.4(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 O2 H2O O1 0.82 2.19 2.880(5) 142.6 1_655 O1 H1O O2 0.82 1.93 2.739(5) 169.1 2_556 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 21.59 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.667 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.059 #===END data_compound_18_CCDC_753049 _database_code_depnum_ccdc_archive 'CCDC 753049' #TrackingRef '3Structures_OrgBiomolChem.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2Z,6Z)-cycloocta-2,6-diene-1,5-dicarbaldehyde ; _chemical_name_common (2Z,6Z)-cycloocta-2,6-diene-1,5-dicarbaldehyde _chemical_melting_point ? _chemical_formula_moiety 'C10 H12 O2' _chemical_formula_sum 'C10 H12 O2' _chemical_formula_weight 164.20 _chemical_absolute_configuration ? 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_Hall '-P 2yn' 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 7.160(4) _cell_length_b 13.956(5) _cell_length_c 8.879(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.312(5) _cell_angle_gamma 90.00 _cell_volume 870.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1779 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 26.022 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.883 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11473 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.97 _reflns_number_total 1701 _reflns_number_gt 1204 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _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^)+(0.0677P)^2^+0.1069P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1701 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1144 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 O1 O 0.13266(18) 0.02346(12) 0.22808(16) 0.0803(5) Uani 1 1 d . . . O2 O 0.82861(19) 0.38640(11) 0.08390(16) 0.0732(4) Uani 1 1 d . . . C1 C 0.3904(2) 0.08862(11) 0.12981(17) 0.0431(4) Uani 1 1 d . . . C2 C 0.2592(2) 0.12621(12) -0.01115(19) 0.0483(4) Uani 1 1 d . . . H2A H 0.1446 0.0874 -0.0308 0.058 Uiso 1 1 calc R . . H2B H 0.3210 0.1195 -0.0985 0.058 Uiso 1 1 calc R . . C3 C 0.2035(2) 0.23061(13) 0.0023(2) 0.0557(5) Uani 1 1 d . . . H3A H 0.1203 0.2486 -0.0934 0.067 Uiso 1 1 calc R . . H3B H 0.1290 0.2347 0.0823 0.067 Uiso 1 1 calc R . . C4 C 0.3578(2) 0.30349(12) 0.03615(19) 0.0495(4) Uani 1 1 d . . . H4 H 0.3225 0.3611 0.0752 0.059 Uiso 1 1 calc R . . C5 C 0.5396(2) 0.29939(11) 0.01935(18) 0.0443(4) Uani 1 1 d . . . C6 C 0.6383(2) 0.21740(13) -0.04139(19) 0.0508(4) Uani 1 1 d . . . H6A H 0.7422 0.2420 -0.0857 0.061 Uiso 1 1 calc R . . H6B H 0.5493 0.1855 -0.1223 0.061 Uiso 1 1 calc R . . C7 C 0.7168(2) 0.14483(13) 0.0837(2) 0.0547(5) Uani 1 1 d . . . H7A H 0.7826 0.0954 0.0377 0.066 Uiso 1 1 calc R . . H7B H 0.8113 0.1772 0.1599 0.066 Uiso 1 1 calc R . . C8 C 0.5798(2) 0.09678(12) 0.16540(19) 0.0477(4) Uani 1 1 d . . . H8 H 0.6359 0.0673 0.2571 0.057 Uiso 1 1 calc R . . C9 C 0.3016(3) 0.03716(14) 0.2407(2) 0.0568(5) Uani 1 1 d . . . H9 H 0.3814 0.0131 0.3278 0.068 Uiso 1 1 calc R . . C10 C 0.6579(3) 0.38206(13) 0.0762(2) 0.0565(5) Uani 1 1 d . . . H10 H 0.5979 0.4351 0.1088 0.068 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0601(9) 0.0993(12) 0.0837(10) 0.0246(8) 0.0200(7) -0.0113(7) O2 0.0613(9) 0.0778(10) 0.0778(10) -0.0074(7) 0.0071(7) -0.0233(7) C1 0.0425(8) 0.0402(9) 0.0458(9) -0.0039(7) 0.0070(6) 0.0000(6) C2 0.0390(8) 0.0556(11) 0.0483(9) 0.0008(8) 0.0038(7) -0.0074(7) C3 0.0376(8) 0.0653(12) 0.0636(11) 0.0122(9) 0.0081(7) 0.0047(8) C4 0.0498(9) 0.0475(10) 0.0510(10) 0.0055(8) 0.0091(7) 0.0086(7) C5 0.0458(8) 0.0458(9) 0.0406(8) 0.0042(7) 0.0068(6) -0.0009(7) C6 0.0417(8) 0.0616(11) 0.0521(10) -0.0086(8) 0.0165(7) -0.0068(7) C7 0.0361(8) 0.0529(11) 0.0749(12) -0.0082(9) 0.0107(7) 0.0038(7) C8 0.0452(9) 0.0438(9) 0.0519(9) -0.0032(7) 0.0037(7) 0.0069(7) C9 0.0565(11) 0.0590(12) 0.0551(11) 0.0080(9) 0.0113(8) 0.0026(8) C10 0.0628(12) 0.0517(11) 0.0536(10) 0.0036(8) 0.0080(8) -0.0054(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 O1 C9 1.208(2) . ? O2 C10 1.212(2) . ? C1 C8 1.336(2) . ? C1 C9 1.461(2) . ? C1 C2 1.504(2) . ? C2 C3 1.521(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.488(2) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.340(2) . ? C4 H4 0.9300 . ? C5 C10 1.461(2) . ? C5 C6 1.500(2) . ? C6 C7 1.526(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.489(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? 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 C8 C1 C9 116.00(15) . . ? C8 C1 C2 127.33(15) . . ? C9 C1 C2 116.67(14) . . ? C1 C2 C3 113.53(14) . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2B 108.9 . . ? C3 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C4 C3 C2 118.34(13) . . ? C4 C3 H3A 107.7 . . ? C2 C3 H3A 107.7 . . ? C4 C3 H3B 107.7 . . ? C2 C3 H3B 107.7 . . ? H3A C3 H3B 107.1 . . ? C5 C4 C3 130.32(16) . . ? C5 C4 H4 114.8 . . ? C3 C4 H4 114.8 . . ? C4 C5 C10 115.95(16) . . ? C4 C5 C6 127.54(15) . . ? C10 C5 C6 116.38(14) . . ? C5 C6 C7 112.13(14) . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 118.04(13) . . ? C8 C7 H7A 107.8 . . ? C6 C7 H7A 107.8 . . ? C8 C7 H7B 107.8 . . ? C6 C7 H7B 107.8 . . ? H7A C7 H7B 107.1 . . ? C1 C8 C7 131.16(16) . . ? C1 C8 H8 114.4 . . ? C7 C8 H8 114.4 . . ? O1 C9 C1 125.15(16) . . ? O1 C9 H9 117.4 . . ? C1 C9 H9 117.4 . . ? O2 C10 C5 124.65(17) . . ? O2 C10 H10 117.7 . . ? C5 C10 H10 117.7 . . ? 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 C8 C1 C2 C3 -84.3(2) . . . . ? C9 C1 C2 C3 95.83(17) . . . . ? C1 C2 C3 C4 57.2(2) . . . . ? C2 C3 C4 C5 19.7(3) . . . . ? C3 C4 C5 C10 -175.15(16) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C7 -85.7(2) . . . . ? C10 C5 C6 C7 89.98(17) . . . . ? C5 C6 C7 C8 59.8(2) . . . . ? C9 C1 C8 C7 -178.76(17) . . . . ? C2 C1 C8 C7 1.4(3) . . . . ? C6 C7 C8 C1 16.7(3) . . . . ? C8 C1 C9 O1 179.49(18) . . . . ? C2 C1 C9 O1 -0.6(3) . . . . ? C4 C5 C10 O2 172.50(17) . . . . ? C6 C5 C10 O2 -3.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.97 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.143 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.049 #===END