# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Lorbach, Volker' ; Institute of Biotechnoligie 2 Forschungszentrum Julich GmbH D-52425 Julich Bundesrepublik Deutschland ; 'Franke, Dirk' ; Institute of Biotechnoligie 2 Forschungszentrum Julich GmbH D-52425 Julich Bundesrepublik Deutschland ; 'Nieger, Martin' ; Institut fur Anorganische Chemie Universitat Bonn Gerhard-Domagk-Str. 1 D-53121 Bonn Bundesrepublik Deutschland ; 'Muller, Michael' ; Institute of Biotechnoligie 2 Forschungszentrum Julich GmbH D-52425 Julich Bundesrepublik Deutschland ; _publ_contact_author_name 'Dr Michael Muller' _publ_contact_author_address ; Institute of Biotechnlology 2 Forschungszentrum Julich Forschungszentrum Julich GmbH Jülich 52425 GERMANY ; _publ_contact_author_phone '049 228 73-5823' _publ_contact_author_fax '049 228 73-5327' _publ_contact_author_email 'MI.MUELLER@FZ-JUELICH.DE' _publ_requested_journal 'J. Chem. Soc. Chem. Comm.' _publ_requested_coeditor_name ? _publ_contact_letter ; enclosed you will fond the necessary data of our publication in J. Chem. Soc. Chem. Comm., MS B110420A ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Cyclohexadiene-trans-diols as versatile starting material in natural products synthesis: Short and efficient synthesis of iso-crotepoxide and ent-senepoxide ; #============================================================================== data_jyk_mm_2_compound_3 _database_code_CSD 174631 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,5-Dihydroxy-7-oxa-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid methyl ester ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H10 O5' _chemical_formula_sum 'C8 H10 O5' _chemical_formula_weight 186.16 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 'P2(1)' #(No.4) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.6140(2) _cell_length_b 4.56550(10) _cell_length_c 11.0991(4) _cell_angle_alpha 90.00 _cell_angle_beta 112.515(2) _cell_angle_gamma 90.00 _cell_volume 403.227(19) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 10591 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 28.3 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 196 _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 30 mm, 2 x 90 sec., 2 deg. 371 frames, 6 sets, mos.= 0.456(2) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 8907 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0206 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1418 _reflns_number_gt 1395 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0427P)^2^+0.1432P] 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 '0.5(10), cannot be determind reliabl.' _refine_ls_number_reflns 1418 _refine_ls_number_parameters 121 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0294 _refine_ls_R_factor_gt 0.0290 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.096 _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 0.3517(2) 0.3720(4) 0.33084(15) 0.0133(3) Uani 1 1 d . . . H1 H 0.3911 0.1665 0.3556 0.016 Uiso 1 1 calc R . . O1 O 0.32300(14) 0.5050(3) 0.43747(11) 0.0148(3) Uani 1 1 d . . . H1O H 0.3113 0.3738 0.4864 0.022 Uiso 1 1 calc R . . C2 C 0.4901(2) 0.5418(4) 0.30725(15) 0.0133(4) Uani 1 1 d . . . H2 H 0.4571 0.7531 0.2989 0.016 Uiso 1 1 calc R . . O2 O 0.64821(14) 0.5187(3) 0.41620(11) 0.0150(3) Uani 1 1 d . . . H2O H 0.6467 0.3717 0.4612 0.023 Uiso 1 1 calc R . . C3 C 0.5083(2) 0.4560(4) 0.18285(17) 0.0152(4) Uani 1 1 d . . . H3 H 0.5993 0.5568 0.1636 0.018 Uiso 1 1 calc R . . O3 O 0.47672(16) 0.1536(3) 0.14260(12) 0.0185(3) Uani 1 1 d . . . C4 C 0.3560(2) 0.3809(4) 0.07009(16) 0.0168(4) Uani 1 1 d . . . H4 H 0.3520 0.4352 -0.0183 0.020 Uiso 1 1 calc R . . C5 C 0.1949(2) 0.3705(4) 0.08877(17) 0.0186(4) Uani 1 1 d . . . H5 H 0.0920 0.3688 0.0148 0.022 Uiso 1 1 calc R . . C6 C 0.1921(2) 0.3636(4) 0.20838(17) 0.0164(4) Uani 1 1 d . . . C7 C 0.0294(2) 0.2944(4) 0.22191(16) 0.0166(4) Uani 1 1 d . . . O4 O -0.10615(16) 0.3837(3) 0.15118(12) 0.0262(3) Uani 1 1 d . . . O5 O 0.05456(15) 0.1062(3) 0.31998(12) 0.0199(3) Uani 1 1 d . . . C8 C -0.0951(2) 0.0074(5) 0.33777(19) 0.0251(4) Uani 1 1 d . . . H8A H -0.1510 0.1753 0.3589 0.038 Uiso 1 1 calc R . . H8B H -0.0639 -0.1350 0.4092 0.038 Uiso 1 1 calc R . . H8C H -0.1718 -0.0849 0.2572 0.038 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 0.0153(8) 0.0127(8) 0.0129(8) -0.0008(7) 0.0065(7) 0.0020(7) O1 0.0210(6) 0.0144(6) 0.0119(6) -0.0004(5) 0.0094(5) 0.0003(5) C2 0.0153(8) 0.0125(9) 0.0115(8) 0.0014(7) 0.0043(6) 0.0014(7) O2 0.0141(5) 0.0152(6) 0.0153(6) 0.0011(5) 0.0050(5) -0.0001(5) C3 0.0197(8) 0.0096(8) 0.0201(9) 0.0004(7) 0.0119(7) -0.0013(6) O3 0.0240(7) 0.0146(6) 0.0194(6) -0.0028(5) 0.0111(5) 0.0017(5) C4 0.0218(9) 0.0157(9) 0.0150(8) 0.0013(7) 0.0093(7) 0.0003(7) C5 0.0176(9) 0.0207(9) 0.0136(8) 0.0007(8) 0.0016(7) 0.0008(8) C6 0.0142(8) 0.0163(8) 0.0196(9) 0.0002(8) 0.0075(7) 0.0002(7) C7 0.0174(9) 0.0199(9) 0.0120(8) -0.0036(7) 0.0052(7) -0.0001(7) O4 0.0142(7) 0.0411(9) 0.0215(7) 0.0080(7) 0.0048(5) 0.0065(6) O5 0.0145(6) 0.0239(7) 0.0212(7) 0.0056(5) 0.0067(5) -0.0018(5) C8 0.0215(9) 0.0325(10) 0.0244(10) 0.0014(9) 0.0123(8) -0.0053(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 C1 O1 1.4332(19) . ? C1 C6 1.519(2) . ? C1 C2 1.526(2) . ? C1 H1 1.0000 . ? O1 H1O 0.8400 . ? C2 O2 1.4379(19) . ? C2 C3 1.500(2) . ? C2 H2 1.0000 . ? O2 H2O 0.8400 . ? C3 O3 1.445(2) . ? C3 C4 1.465(3) . ? C3 H3 1.0000 . ? O3 C4 1.471(2) . ? C4 C5 1.481(2) . ? C4 H4 1.0000 . ? C5 C6 1.337(3) . ? C5 H5 0.9500 . ? C6 C7 1.500(2) . ? C7 O4 1.201(2) . ? C7 O5 1.338(2) . ? O5 C8 1.449(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C1 C6 111.51(13) . . ? O1 C1 C2 108.63(13) . . ? C6 C1 C2 110.97(13) . . ? O1 C1 H1 108.6 . . ? C6 C1 H1 108.6 . . ? C2 C1 H1 108.6 . . ? C1 O1 H1O 109.5 . . ? O2 C2 C3 110.82(13) . . ? O2 C2 C1 111.67(12) . . ? C3 C2 C1 112.91(13) . . ? O2 C2 H2 107.0 . . ? C3 C2 H2 107.0 . . ? C1 C2 H2 107.0 . . ? C2 O2 H2O 109.5 . . ? O3 C3 C4 60.73(11) . . ? O3 C3 C2 117.40(13) . . ? C4 C3 C2 118.17(14) . . ? O3 C3 H3 116.3 . . ? C4 C3 H3 116.3 . . ? C2 C3 H3 116.3 . . ? C3 O3 C4 60.34(11) . . ? C3 C4 O3 58.93(11) . . ? C3 C4 C5 117.94(14) . . ? O3 C4 C5 113.88(14) . . ? C3 C4 H4 117.6 . . ? O3 C4 H4 117.6 . . ? C5 C4 H4 117.6 . . ? C6 C5 C4 120.92(15) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 118.50(16) . . ? C5 C6 C1 122.25(15) . . ? C7 C6 C1 118.42(14) . . ? O4 C7 O5 124.33(16) . . ? O4 C7 C6 125.08(16) . . ? O5 C7 C6 110.51(14) . . ? C7 O5 C8 115.80(14) . . ? O5 C8 H8A 109.5 . . ? O5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C1 C2 O2 64.86(16) . . . . ? C6 C1 C2 O2 -172.21(13) . . . . ? O1 C1 C2 C3 -169.46(13) . . . . ? C6 C1 C2 C3 -46.53(19) . . . . ? O2 C2 C3 O3 92.22(17) . . . . ? C1 C2 C3 O3 -33.9(2) . . . . ? O2 C2 C3 C4 161.91(14) . . . . ? C1 C2 C3 C4 35.8(2) . . . . ? C2 C3 O3 C4 108.60(16) . . . . ? C2 C3 C4 O3 -107.36(16) . . . . ? O3 C3 C4 C5 102.44(17) . . . . ? C2 C3 C4 C5 -4.9(2) . . . . ? C3 O3 C4 C5 -109.36(16) . . . . ? C3 C4 C5 C6 -14.8(3) . . . . ? O3 C4 C5 C6 51.3(2) . . . . ? C4 C5 C6 C7 -168.20(16) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? O1 C1 C6 C5 151.03(18) . . . . ? C2 C1 C6 C5 29.8(3) . . . . ? O1 C1 C6 C7 -39.5(2) . . . . ? C2 C1 C6 C7 -160.77(15) . . . . ? C5 C6 C7 O4 -40.3(3) . . . . ? C1 C6 C7 O4 149.86(18) . . . . ? C5 C6 C7 O5 136.49(18) . . . . ? C1 C6 C7 O5 -33.4(2) . . . . ? O4 C7 O5 C8 0.6(3) . . . . ? C6 C7 O5 C8 -176.23(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 O1 H1O O2 0.84 1.91 2.7054(17) 158.8 2_646 O2 H2O O1 0.84 1.98 2.8093(17) 170.5 2_646 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.581 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.044 #============================================================================== data_mm02_compound_14 _database_code_CSD 174632 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Benzoic acid 5,6-dihydroxy-3,8-dioxa-tricyclo[5.1.0.0^2,4^]oct-4- ylmethyl ester ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 O6' _chemical_formula_sum 'C14 H14 O6' _chemical_formula_weight 278.25 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 orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1)' #(No.19) 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 8.8867(2) _cell_length_b 11.7119(2) _cell_length_c 12.0177(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1250.80(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 5616 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description blocks _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.117 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 40 mm; 50 sec./deg., 2 deg.,8 sets, 492 frames; mos.= 1.069(2) deg. ; _diffrn_ambient_temperature 123(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 'Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 24670 _diffrn_reflns_av_R_equivalents 0.0309 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2206 _reflns_number_gt 2157 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0362P)^2^+0.1548P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack '-0.1(6); cannot be determined reliabl.' _refine_ls_number_reflns 2206 _refine_ls_number_parameters 187 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0214 _refine_ls_wR_factor_ref 0.0563 _refine_ls_wR_factor_gt 0.0559 _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 0.83674(10) 0.53788(7) 0.40866(7) 0.02418(19) Uani 1 1 d D . . H1O H 0.8748(16) 0.5341(13) 0.3454(12) 0.036 Uiso 1 1 d D . . O2 O 0.45831(9) 0.43413(7) 0.33310(7) 0.02210(19) Uani 1 1 d D . . H2O H 0.4147(15) 0.4973(11) 0.3327(13) 0.033 Uiso 1 1 d D . . O3 O 0.79645(9) 0.51757(7) 0.17420(7) 0.02173(18) Uani 1 1 d . . . O4 O 0.49471(9) 0.67477(6) 0.29542(6) 0.02004(18) Uani 1 1 d . . . O5 O 0.62411(9) 0.74833(7) 0.52901(6) 0.02131(18) Uani 1 1 d . . . O6 O 0.73195(10) 0.91447(7) 0.57665(7) 0.0268(2) Uani 1 1 d . . . C1 C 0.67703(13) 0.54589(9) 0.39426(9) 0.0183(2) Uani 1 1 d . . . H1 H 0.6291 0.5388 0.4692 0.022 Uiso 1 1 calc R . . C2 C 0.61695(13) 0.44882(9) 0.32097(9) 0.0193(2) Uani 1 1 d . . . H2 H 0.6666 0.3765 0.3456 0.023 Uiso 1 1 calc R . . C3 C 0.65261(13) 0.46545(9) 0.19889(9) 0.0199(2) Uani 1 1 d . . . H3 H 0.6185 0.4037 0.1472 0.024 Uiso 1 1 calc R . . C4 C 0.65846(13) 0.58128(9) 0.15284(9) 0.0201(2) Uani 1 1 d . . . H4 H 0.6280 0.5905 0.0732 0.024 Uiso 1 1 calc R . . C5 C 0.63131(13) 0.68014(9) 0.22786(9) 0.0191(2) Uani 1 1 d . . . H5 H 0.6603 0.7570 0.1988 0.023 Uiso 1 1 calc R . . C6 C 0.64044(11) 0.66411(9) 0.34894(9) 0.0164(2) Uani 1 1 d . . . C7 C 0.68682(14) 0.76411(10) 0.41840(9) 0.0205(2) Uani 1 1 d . . . H7A H 0.7979 0.7687 0.4224 0.025 Uiso 1 1 calc R . . H7B H 0.6485 0.8358 0.3852 0.025 Uiso 1 1 calc R . . C8 C 0.66176(12) 0.82996(9) 0.60230(9) 0.0193(2) Uani 1 1 d . . . C9 C 0.60861(13) 0.80457(10) 0.71736(10) 0.0216(2) Uani 1 1 d . . . C10 C 0.52105(13) 0.70875(10) 0.74156(10) 0.0223(3) Uani 1 1 d . . . H10 H 0.4963 0.6558 0.6845 0.027 Uiso 1 1 calc R . . C11 C 0.47017(14) 0.69133(11) 0.84993(11) 0.0286(3) Uani 1 1 d . . . H11 H 0.4093 0.6270 0.8669 0.034 Uiso 1 1 calc R . . C12 C 0.50875(16) 0.76845(12) 0.93306(10) 0.0327(3) Uani 1 1 d . . . H12 H 0.4727 0.7569 1.0066 0.039 Uiso 1 1 calc R . . C13 C 0.59908(16) 0.86200(12) 0.91001(11) 0.0333(3) Uani 1 1 d . . . H13 H 0.6273 0.9131 0.9678 0.040 Uiso 1 1 calc R . . C14 C 0.64800(14) 0.88043(11) 0.80181(10) 0.0279(3) Uani 1 1 d . . . H14 H 0.7086 0.9450 0.7852 0.033 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 0.0231(4) 0.0268(4) 0.0226(4) 0.0022(4) -0.0029(3) 0.0038(4) O2 0.0235(4) 0.0146(4) 0.0281(4) -0.0021(3) 0.0068(4) -0.0016(3) O3 0.0233(4) 0.0209(4) 0.0210(4) 0.0014(3) 0.0051(3) 0.0025(3) O4 0.0194(4) 0.0197(4) 0.0211(4) -0.0009(3) 0.0003(3) 0.0021(3) O5 0.0259(4) 0.0203(4) 0.0177(4) -0.0051(3) 0.0036(3) -0.0037(3) O6 0.0303(5) 0.0235(4) 0.0267(4) -0.0053(4) -0.0024(4) -0.0061(4) C1 0.0210(5) 0.0188(5) 0.0151(5) 0.0022(4) 0.0014(5) 0.0009(4) C2 0.0224(6) 0.0139(5) 0.0216(6) -0.0004(4) 0.0038(4) 0.0002(4) C3 0.0213(6) 0.0184(5) 0.0200(5) -0.0028(4) 0.0021(4) -0.0005(5) C4 0.0235(6) 0.0214(5) 0.0155(5) 0.0012(4) -0.0009(5) 0.0026(5) C5 0.0207(6) 0.0174(5) 0.0192(5) 0.0023(4) 0.0013(5) 0.0009(4) C6 0.0162(5) 0.0165(5) 0.0164(5) -0.0008(4) 0.0028(4) 0.0004(4) C7 0.0237(6) 0.0191(5) 0.0188(6) -0.0014(5) 0.0036(5) -0.0033(5) C8 0.0169(5) 0.0195(5) 0.0215(5) -0.0050(4) -0.0023(5) 0.0036(5) C9 0.0194(5) 0.0254(6) 0.0201(5) -0.0043(5) -0.0026(5) 0.0076(5) C10 0.0224(6) 0.0232(6) 0.0213(5) -0.0013(5) -0.0027(5) 0.0096(5) C11 0.0293(6) 0.0297(7) 0.0268(6) 0.0066(5) 0.0034(5) 0.0119(5) C12 0.0356(7) 0.0435(8) 0.0189(6) 0.0010(6) 0.0032(5) 0.0223(6) C13 0.0361(7) 0.0402(8) 0.0237(6) -0.0113(6) -0.0034(5) 0.0118(6) C14 0.0278(6) 0.0312(6) 0.0247(6) -0.0094(5) -0.0024(5) 0.0064(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.4329(14) . ? O1 H1O 0.834(13) . ? O2 C2 1.4277(14) . ? O2 H2O 0.836(13) . ? O3 C3 1.4473(14) . ? O3 C4 1.4582(13) . ? O4 C6 1.4513(13) . ? O4 C5 1.4617(14) . ? O5 C8 1.3423(14) . ? O5 C7 1.4532(13) . ? O6 C8 1.2099(15) . ? C1 C6 1.5230(15) . ? C1 C2 1.5341(15) . ? C1 H1 1.0000 . ? C2 C3 1.5135(15) . ? C2 H2 1.0000 . ? C3 C4 1.4660(15) . ? C3 H3 1.0000 . ? C4 C5 1.4872(16) . ? C4 H4 1.0000 . ? C5 C6 1.4694(15) . ? C5 H5 1.0000 . ? C6 C7 1.4962(15) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.4911(16) . ? C9 C14 1.3935(17) . ? C9 C10 1.3962(18) . ? C10 C11 1.3937(18) . ? C10 H10 0.9500 . ? C11 C12 1.3898(19) . ? C11 H11 0.9500 . ? C12 C13 1.386(2) . ? C12 H12 0.9500 . ? C13 C14 1.3880(18) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? 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 O1 H1O 107.2(11) . . ? C2 O2 H2O 110.5(10) . . ? C3 O3 C4 60.60(7) . . ? C6 O4 C5 60.59(7) . . ? C8 O5 C7 114.46(8) . . ? O1 C1 C6 108.31(9) . . ? O1 C1 C2 111.45(9) . . ? C6 C1 C2 113.21(9) . . ? O1 C1 H1 107.9 . . ? C6 C1 H1 107.9 . . ? C2 C1 H1 107.9 . . ? O2 C2 C3 108.74(9) . . ? O2 C2 C1 111.99(9) . . ? C3 C2 C1 112.85(9) . . ? O2 C2 H2 107.7 . . ? C3 C2 H2 107.7 . . ? C1 C2 H2 107.7 . . ? O3 C3 C4 60.07(7) . . ? O3 C3 C2 115.97(9) . . ? C4 C3 C2 119.50(9) . . ? O3 C3 H3 116.4 . . ? C4 C3 H3 116.4 . . ? C2 C3 H3 116.4 . . ? O3 C4 C3 59.33(7) . . ? O3 C4 C5 115.35(9) . . ? C3 C4 C5 119.07(9) . . ? O3 C4 H4 116.8 . . ? C3 C4 H4 116.8 . . ? C5 C4 H4 116.8 . . ? O4 C5 C6 59.36(7) . . ? O4 C5 C4 115.97(9) . . ? C6 C5 C4 119.46(10) . . ? O4 C5 H5 116.6 . . ? C6 C5 H5 116.6 . . ? C4 C5 H5 116.6 . . ? O4 C6 C5 60.06(7) . . ? O4 C6 C7 115.20(9) . . ? C5 C6 C7 117.88(9) . . ? O4 C6 C1 115.29(9) . . ? C5 C6 C1 118.82(9) . . ? C7 C6 C1 116.96(9) . . ? O5 C7 C6 107.76(8) . . ? O5 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? O5 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? O6 C8 O5 122.95(10) . . ? O6 C8 C9 124.25(10) . . ? O5 C8 C9 112.80(10) . . ? C14 C9 C10 120.05(11) . . ? C14 C9 C8 117.95(11) . . ? C10 C9 C8 122.00(10) . . ? C11 C10 C9 119.55(11) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 119.77(12) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 120.86(11) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.44(12) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C13 C14 C9 120.30(13) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.9 . . ? 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 C1 C2 O2 162.03(9) . . . . ? C6 C1 C2 O2 -75.57(11) . . . . ? O1 C1 C2 C3 -74.87(11) . . . . ? C6 C1 C2 C3 47.52(13) . . . . ? C4 O3 C3 C2 -110.59(11) . . . . ? O2 C2 C3 O3 160.64(9) . . . . ? C1 C2 C3 O3 35.76(13) . . . . ? O2 C2 C3 C4 91.87(12) . . . . ? C1 C2 C3 C4 -33.01(15) . . . . ? C3 O3 C4 C5 110.13(10) . . . . ? C2 C3 C4 O3 104.76(11) . . . . ? O3 C3 C4 C5 -103.87(11) . . . . ? C2 C3 C4 C5 0.89(16) . . . . ? C6 O4 C5 C4 110.32(11) . . . . ? O3 C4 C5 O4 -118.77(10) . . . . ? C3 C4 C5 O4 -51.26(14) . . . . ? O3 C4 C5 C6 -50.86(14) . . . . ? C3 C4 C5 C6 16.66(16) . . . . ? C5 O4 C6 C7 108.99(10) . . . . ? C5 O4 C6 C1 -110.07(10) . . . . ? C4 C5 C6 O4 -104.47(11) . . . . ? O4 C5 C6 C7 -104.55(10) . . . . ? C4 C5 C6 C7 150.98(10) . . . . ? O4 C5 C6 C1 104.23(10) . . . . ? C4 C5 C6 C1 -0.24(15) . . . . ? O1 C1 C6 O4 160.42(8) . . . . ? C2 C1 C6 O4 36.30(12) . . . . ? O1 C1 C6 C5 92.15(11) . . . . ? C2 C1 C6 C5 -31.98(14) . . . . ? O1 C1 C6 C7 -59.34(12) . . . . ? C2 C1 C6 C7 176.54(9) . . . . ? C8 O5 C7 C6 177.46(9) . . . . ? O4 C6 C7 O5 86.29(10) . . . . ? C5 C6 C7 O5 154.26(9) . . . . ? C1 C6 C7 O5 -53.98(12) . . . . ? C7 O5 C8 O6 5.64(15) . . . . ? C7 O5 C8 C9 -174.07(9) . . . . ? O6 C8 C9 C14 -3.01(17) . . . . ? O5 C8 C9 C14 176.70(10) . . . . ? O6 C8 C9 C10 176.52(11) . . . . ? O5 C8 C9 C10 -3.78(15) . . . . ? C14 C9 C10 C11 1.71(17) . . . . ? C8 C9 C10 C11 -177.80(10) . . . . ? C9 C10 C11 C12 -0.91(18) . . . . ? C10 C11 C12 C13 -0.86(19) . . . . ? C11 C12 C13 C14 1.82(19) . . . . ? C12 C13 C14 C9 -1.00(19) . . . . ? C10 C9 C14 C13 -0.76(18) . . . . ? C8 C9 C14 C13 178.77(11) . . . . ? 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 O1 H1O O3 0.834(13) 2.180(15) 2.8502(12) 137.4(13) . O2 H2O O4 0.836(13) 2.242(14) 2.8728(11) 132.4(13) . O2 H2O O6 0.836(13) 2.211(14) 2.8926(12) 138.8(14) 4_466 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.143 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.031 #============================================================================== # End of Crystallographic Information File