# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof. Faiz Ahmed Khan' _publ_contact_author_address ;Department of Chemistry Indian Institute of Technology Kanpur - 208 016 India ; _publ_contact_author_email faiz@iitk.ac.in _publ_contact_author_phone '(+91) 512-2597864' _publ_contact_author_fax '(+91) 512-2597436' _publ_section_title ; Lead(IV) acetate: intriguing reactivity profile ; loop_ _publ_author_name 'Faiz Ahmed Khan' L.Soma 'Ch. Sudheer ' data_compound_1d _database_code_depnum_ccdc_archive 'CCDC 649155' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 Br2 O5' _chemical_formula_sum 'C16 H22 Br2 O5' _chemical_formula_weight 454.16 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9742(8) _cell_length_b 17.9301(16) _cell_length_c 10.6917(10) _cell_angle_alpha 90.00 _cell_angle_beta 106.031(2) _cell_angle_gamma 90.00 _cell_volume 1653.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3136 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 28.02 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.824 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 4.925 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4709 _exptl_absorpt_correction_T_max 0.5669 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ? _diffrn_ambient_temperature 100(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 'CCD area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 10726 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 28.29 _reflns_number_total 4062 _reflns_number_gt 3101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 ( Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 ( Bruker, 2003)' _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0100P)^2^+26.4037P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4062 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0791 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.0980 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.156 _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 Br1 Br 0.47316(7) 0.72333(4) 0.72360(7) 0.01748(17) Uani 1 1 d . . . Br2 Br 1.09310(7) 0.80633(4) 0.67470(7) 0.01761(17) Uani 1 1 d . . . O4 O 0.8185(6) 0.9406(3) 0.6216(4) 0.0168(10) Uani 1 1 d . . . O2 O 0.8823(5) 0.6898(3) 0.7861(4) 0.0154(9) Uani 1 1 d . . . O5 O 0.6718(6) 0.9289(3) 0.2746(5) 0.0203(10) Uani 1 1 d . . . O1 O 0.7344(5) 0.7076(2) 0.5721(4) 0.0144(9) Uani 1 1 d . . . O3 O 0.5046(5) 0.8788(3) 0.6001(5) 0.0192(10) Uani 1 1 d . . . C15 C 0.7615(9) 0.9783(4) 0.4985(6) 0.0188(14) Uani 1 1 d . . . H15A H 0.8208 1.0233 0.4959 0.023 Uiso 1 1 calc R . . H15B H 0.6531 0.9915 0.4830 0.023 Uiso 1 1 calc R . . C7 C 0.7948(7) 0.7394(4) 0.6951(6) 0.0105(12) Uani 1 1 d . . . C3 C 0.9044(8) 0.8356(4) 0.8497(7) 0.0194(14) Uani 1 1 d . . . H3 H 0.9872 0.8057 0.9066 0.023 Uiso 1 1 calc R . . C2 C 0.7458(8) 0.8098(4) 0.8673(6) 0.0154(13) Uani 1 1 d . . . H2 H 0.7626 0.7691 0.9309 0.019 Uiso 1 1 calc R . . C9 C 0.8407(9) 0.6636(4) 0.5238(7) 0.0212(15) Uani 1 1 d . . . H9A H 0.7882 0.6443 0.4394 0.032 Uiso 1 1 calc R . . H9B H 0.8788 0.6230 0.5824 0.032 Uiso 1 1 calc R . . H9C H 0.9260 0.6943 0.5174 0.032 Uiso 1 1 calc R . . C14 C 0.7828(8) 0.9216(4) 0.3981(6) 0.0158(13) Uani 1 1 d . . . H14 H 0.8879 0.9255 0.3881 0.019 Uiso 1 1 calc R . . C5 C 0.7780(7) 0.8645(4) 0.6029(7) 0.0153(13) Uani 1 1 d . . . C10 C 0.6736(8) 0.8769(4) 0.9185(6) 0.0149(13) Uani 1 1 d . . . H10A H 0.5636 0.8803 0.8751 0.018 Uiso 1 1 calc R . . H10B H 0.6875 0.8724 1.0114 0.018 Uiso 1 1 calc R . . C12 C 0.9235(7) 0.9163(4) 0.8947(6) 0.0143(13) Uani 1 1 d . . . H12A H 0.9687 0.9457 0.8382 0.017 Uiso 1 1 calc R . . H12B H 0.9906 0.9195 0.9829 0.017 Uiso 1 1 calc R . . C4 C 0.8885(7) 0.8138(4) 0.7059(7) 0.0185(14) Uani 1 1 d . . . C8 C 0.8064(8) 0.6227(4) 0.8070(7) 0.0203(15) Uani 1 1 d . . . H8A H 0.8771 0.5926 0.8710 0.030 Uiso 1 1 calc R . . H8B H 0.7731 0.5954 0.7268 0.030 Uiso 1 1 calc R . . H8C H 0.7180 0.6349 0.8371 0.030 Uiso 1 1 calc R . . C16 C 0.6864(9) 0.9979(4) 0.2135(7) 0.0239(16) Uani 1 1 d . . . H16A H 0.6098 1.0006 0.1308 0.036 Uiso 1 1 calc R . . H16B H 0.7880 1.0014 0.2007 0.036 Uiso 1 1 calc R . . H16C H 0.6715 1.0384 0.2676 0.036 Uiso 1 1 calc R . . C1 C 0.6611(7) 0.7798(4) 0.7323(6) 0.0119(12) Uani 1 1 d . . . C11 C 0.7587(8) 0.9452(4) 0.8886(7) 0.0190(14) Uani 1 1 d . . . H11A H 0.7633 0.9841 0.9525 0.023 Uiso 1 1 calc R . . H11B H 0.7077 0.9647 0.8028 0.023 Uiso 1 1 calc R . . C6 C 0.6249(8) 0.8456(4) 0.6376(6) 0.0153(13) Uani 1 1 d . . . C13 C 0.7623(8) 0.8471(4) 0.4577(6) 0.0168(13) Uani 1 1 d . . . H13A H 0.8416 0.8122 0.4495 0.020 Uiso 1 1 calc R . . H13B H 0.6612 0.8261 0.4158 0.020 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 Br1 0.0126(3) 0.0229(4) 0.0168(3) -0.0012(3) 0.0039(2) -0.0034(3) Br2 0.0119(3) 0.0221(4) 0.0189(3) -0.0017(3) 0.0043(2) -0.0002(3) O4 0.024(2) 0.013(2) 0.012(2) -0.0038(18) 0.0028(19) 0.0018(19) O2 0.015(2) 0.019(2) 0.011(2) 0.0007(19) 0.0013(18) 0.0045(19) O5 0.023(3) 0.018(3) 0.018(2) 0.001(2) 0.002(2) -0.004(2) O1 0.013(2) 0.010(2) 0.017(2) -0.0044(17) -0.0014(18) -0.0032(17) O3 0.015(2) 0.025(3) 0.016(2) 0.000(2) 0.0010(19) 0.008(2) C15 0.028(4) 0.013(3) 0.015(3) 0.004(3) 0.006(3) 0.005(3) C7 0.007(3) 0.018(3) 0.005(3) 0.007(2) 0.000(2) 0.002(2) C3 0.016(3) 0.020(4) 0.019(3) 0.003(3) 0.000(3) 0.008(3) C2 0.017(3) 0.017(3) 0.010(3) -0.004(3) 0.000(2) 0.000(3) C9 0.029(4) 0.013(3) 0.022(4) -0.001(3) 0.008(3) 0.006(3) C14 0.020(3) 0.014(3) 0.015(3) 0.003(3) 0.007(3) 0.000(3) C5 0.008(3) 0.015(3) 0.020(3) 0.002(3) -0.001(2) 0.003(2) C10 0.016(3) 0.015(3) 0.014(3) -0.007(3) 0.006(3) -0.002(3) C12 0.016(3) 0.017(3) 0.013(3) -0.005(3) 0.009(3) -0.001(3) C4 0.006(3) 0.020(4) 0.025(4) 0.001(3) -0.003(3) 0.004(3) C8 0.023(3) 0.016(3) 0.022(4) 0.005(3) 0.006(3) -0.008(3) C16 0.039(4) 0.019(4) 0.015(3) 0.005(3) 0.010(3) -0.005(3) C1 0.013(3) 0.012(3) 0.010(3) 0.004(2) 0.001(2) -0.002(2) C11 0.022(3) 0.022(4) 0.015(3) -0.005(3) 0.009(3) 0.003(3) C6 0.015(3) 0.013(3) 0.014(3) 0.007(2) -0.002(2) 0.005(2) C13 0.020(3) 0.015(3) 0.015(3) -0.001(3) 0.003(3) 0.005(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 Br1 C1 1.947(6) . ? Br2 C4 1.959(7) . ? O4 C5 1.412(8) . ? O4 C15 1.442(8) . ? O2 C7 1.390(7) . ? O2 C8 1.431(8) . ? O5 C16 1.423(8) . ? O5 C14 1.424(8) . ? O1 C7 1.398(7) . ? O1 C9 1.438(8) . ? O3 C6 1.201(8) . ? C15 C14 1.528(9) . ? C7 C1 1.545(9) . ? C7 C4 1.564(9) . ? C3 C12 1.520(10) . ? C3 C4 1.554(10) . ? C3 C2 1.558(10) . ? C2 C1 1.531(9) . ? C2 C10 1.537(9) . ? C14 C13 1.513(9) . ? C5 C13 1.551(9) . ? C5 C4 1.555(9) . ? C5 C6 1.556(9) . ? C10 C11 1.524(10) . ? C12 C11 1.551(9) . ? C1 C6 1.530(9) . ? 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 C5 O4 C15 108.2(5) . . ? C7 O2 C8 116.5(5) . . ? C16 O5 C14 112.1(5) . . ? C7 O1 C9 116.0(5) . . ? O4 C15 C14 104.3(5) . . ? O2 C7 O1 113.2(5) . . ? O2 C7 C1 116.7(5) . . ? O1 C7 C1 107.9(5) . . ? O2 C7 C4 107.8(5) . . ? O1 C7 C4 118.6(5) . . ? C1 C7 C4 91.2(5) . . ? C12 C3 C4 121.6(6) . . ? C12 C3 C2 105.7(5) . . ? C4 C3 C2 102.0(5) . . ? C1 C2 C10 117.5(5) . . ? C1 C2 C3 102.9(5) . . ? C10 C2 C3 107.5(5) . . ? O5 C14 C13 109.6(5) . . ? O5 C14 C15 113.5(5) . . ? C13 C14 C15 103.8(5) . . ? O4 C5 C13 106.5(5) . . ? O4 C5 C4 112.1(5) . . ? C13 C5 C4 117.0(6) . . ? O4 C5 C6 112.8(5) . . ? C13 C5 C6 110.7(5) . . ? C4 C5 C6 97.8(5) . . ? C11 C10 C2 105.6(5) . . ? C3 C12 C11 106.4(5) . . ? C3 C4 C5 114.8(6) . . ? C3 C4 C7 100.8(5) . . ? C5 C4 C7 102.8(5) . . ? C3 C4 Br2 110.6(4) . . ? C5 C4 Br2 111.3(5) . . ? C7 C4 Br2 116.1(5) . . ? C6 C1 C2 108.2(5) . . ? C6 C1 C7 103.2(5) . . ? C2 C1 C7 100.9(5) . . ? C6 C1 Br1 110.3(4) . . ? C2 C1 Br1 115.2(4) . . ? C7 C1 Br1 117.9(4) . . ? C10 C11 C12 104.5(6) . . ? O3 C6 C1 127.7(6) . . ? O3 C6 C5 125.7(6) . . ? C1 C6 C5 106.6(5) . . ? C14 C13 C5 104.8(5) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.512 _refine_diff_density_min -1.341 _refine_diff_density_rms 0.297 # = = = END data_compound_6c _database_code_depnum_ccdc_archive 'CCDC 649156' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H24 Cl2 O5' _chemical_formula_sum 'C17 H24 Cl2 O5' _chemical_formula_weight 379.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 c a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 11.5727(9) _cell_length_b 11.7784(10) _cell_length_c 25.579(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3486.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4877 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 24.91 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.397 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9320 _exptl_absorpt_correction_T_max 0.9502 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ? _diffrn_ambient_temperature 100(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 'CCD area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 22182 _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.35 _reflns_number_total 7292 _reflns_number_gt 6475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0493P)^2^+5.1608P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.81(6) _refine_ls_number_reflns 7292 _refine_ls_number_parameters 433 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 0.3585(3) 0.0999(3) 0.37537(15) 0.0145(7) Uani 1 1 d . . . C2 C 0.4352(3) 0.0325(3) 0.41478(15) 0.0138(7) Uani 1 1 d . . . H2 H 0.4697 -0.0325 0.3966 0.017 Uiso 1 1 calc R . . C3 C 0.5325(3) 0.1189(3) 0.42881(15) 0.0155(7) Uani 1 1 d . . . H3 H 0.6021 0.0934 0.4104 0.019 Uiso 1 1 calc R . . C4 C 0.4923(3) 0.2293(3) 0.40093(16) 0.0148(7) Uani 1 1 d . . . C5 C 0.3787(3) 0.2795(3) 0.42385(16) 0.0164(8) Uani 1 1 d . . . C6 C 0.2919(3) 0.1881(3) 0.40619(15) 0.0156(8) Uani 1 1 d . . . C7 C 0.4475(3) 0.1798(3) 0.34735(14) 0.0121(7) Uani 1 1 d . . . C8 C 0.5070(3) 0.0654(4) 0.27551(17) 0.0211(8) Uani 1 1 d . . . H8A H 0.5754 0.0343 0.2599 0.032 Uiso 1 1 calc R . . H8B H 0.4688 0.1140 0.2508 0.032 Uiso 1 1 calc R . . H8C H 0.4560 0.0049 0.2854 0.032 Uiso 1 1 calc R . . C9 C 0.4452(4) 0.3336(4) 0.28440(17) 0.0222(8) Uani 1 1 d . . . H9A H 0.3921 0.3794 0.2648 0.033 Uiso 1 1 calc R . . H9B H 0.4947 0.2930 0.2608 0.033 Uiso 1 1 calc R . . H9C H 0.4911 0.3814 0.3066 0.033 Uiso 1 1 calc R . . C10 C 0.3721(3) -0.0101(3) 0.46317(15) 0.0193(8) Uani 1 1 d . . . H10A H 0.3133 -0.0643 0.4528 0.023 Uiso 1 1 calc R . . H10B H 0.3338 0.0532 0.4802 0.023 Uiso 1 1 calc R . . C11 C 0.4555(4) -0.0667(4) 0.50193(18) 0.0249(9) Uani 1 1 d . . . H11A H 0.4697 -0.1442 0.4909 0.030 Uiso 1 1 calc R . . H11B H 0.4197 -0.0691 0.5362 0.030 Uiso 1 1 calc R . . C12 C 0.5714(4) -0.0034(4) 0.50591(17) 0.0213(8) Uani 1 1 d . . . H12A H 0.5971 -0.0038 0.5420 0.026 Uiso 1 1 calc R . . H12B H 0.6289 -0.0432 0.4852 0.026 Uiso 1 1 calc R . . C13 C 0.5626(3) 0.1199(3) 0.48677(15) 0.0177(8) Uani 1 1 d . . . H13A H 0.5033 0.1598 0.5063 0.021 Uiso 1 1 calc R . . H13B H 0.6356 0.1586 0.4922 0.021 Uiso 1 1 calc R . . C14 C 0.3420(3) 0.3994(3) 0.40505(15) 0.0171(8) Uani 1 1 d . . . H14A H 0.4020 0.4335 0.3837 0.021 Uiso 1 1 calc R . . H14B H 0.2711 0.3957 0.3849 0.021 Uiso 1 1 calc R . . C15 C 0.3240(3) 0.4670(3) 0.45529(16) 0.0192(8) Uani 1 1 d . . . H15 H 0.2574 0.5179 0.4525 0.023 Uiso 1 1 calc R . . C16 C 0.3032(3) 0.3748(3) 0.49475(17) 0.0197(8) Uani 1 1 d . . . H16A H 0.3213 0.4009 0.5298 0.024 Uiso 1 1 calc R . . H16B H 0.2234 0.3498 0.4938 0.024 Uiso 1 1 calc R . . C17 C 0.4473(5) 0.6224(4) 0.4402(2) 0.0383(12) Uani 1 1 d . . . H17A H 0.5162 0.6593 0.4524 0.057 Uiso 1 1 calc R . . H17B H 0.3834 0.6740 0.4425 0.057 Uiso 1 1 calc R . . H17C H 0.4577 0.5995 0.4045 0.057 Uiso 1 1 calc R . . C18 C 0.4593(3) 0.3491(3) 0.68838(17) 0.0167(8) Uani 1 1 d . . . C19 C 0.5505(3) 0.4039(3) 0.65262(16) 0.0175(8) Uani 1 1 d . . . H19 H 0.5797 0.4711 0.6710 0.021 Uiso 1 1 calc R . . C20 C 0.6511(3) 0.3148(3) 0.65193(15) 0.0153(7) Uani 1 1 d . . . H20 H 0.7206 0.3503 0.6665 0.018 Uiso 1 1 calc R . . C21 C 0.6076(3) 0.2240(3) 0.69060(15) 0.0158(8) Uani 1 1 d . . . C22 C 0.5076(3) 0.1595(3) 0.66551(15) 0.0149(7) Uani 1 1 d . . . C23 C 0.4020(3) 0.2413(3) 0.66574(14) 0.0147(7) Uani 1 1 d . . . C24 C 0.5405(3) 0.2967(3) 0.73149(15) 0.0155(7) Uani 1 1 d . . . C25 C 0.6920(3) 0.3516(4) 0.79094(17) 0.0219(9) Uani 1 1 d . . . H25A H 0.7280 0.4184 0.8050 0.033 Uiso 1 1 calc R . . H25B H 0.7485 0.3072 0.7726 0.033 Uiso 1 1 calc R . . H25C H 0.6599 0.3075 0.8189 0.033 Uiso 1 1 calc R . . C26 C 0.4276(4) 0.2677(4) 0.80987(17) 0.0258(9) Uani 1 1 d . . . H26A H 0.3989 0.2073 0.8315 0.039 Uiso 1 1 calc R . . H26B H 0.3639 0.3113 0.7966 0.039 Uiso 1 1 calc R . . H26C H 0.4772 0.3159 0.8302 0.039 Uiso 1 1 calc R . . C27 C 0.5195(4) 0.4417(4) 0.59704(17) 0.0276(10) Uani 1 1 d . . . H27A H 0.4822 0.3802 0.5783 0.033 Uiso 1 1 calc R . . H27B H 0.4668 0.5058 0.5982 0.033 Uiso 1 1 calc R . . C28 C 0.6300(4) 0.4751(4) 0.56985(19) 0.0319(11) Uani 1 1 d . . . H28A H 0.6703 0.5312 0.5908 0.038 Uiso 1 1 calc R . . H28B H 0.6117 0.5094 0.5364 0.038 Uiso 1 1 calc R . . C29 C 0.7097(4) 0.3717(4) 0.56108(16) 0.0296(11) Uani 1 1 d . . . H29A H 0.7039 0.3475 0.5249 0.036 Uiso 1 1 calc R . . H29B H 0.7891 0.3939 0.5676 0.036 Uiso 1 1 calc R . . C30 C 0.6783(4) 0.2719(4) 0.59695(16) 0.0220(9) Uani 1 1 d . . . H30A H 0.6116 0.2323 0.5829 0.026 Uiso 1 1 calc R . . H30B H 0.7422 0.2188 0.5984 0.026 Uiso 1 1 calc R . . C31 C 0.2988(3) 0.1881(3) 0.69603(16) 0.0178(8) Uani 1 1 d . . . H31A H 0.3210 0.1161 0.7115 0.021 Uiso 1 1 calc R . . H31B H 0.2729 0.2386 0.7236 0.021 Uiso 1 1 calc R . . C32 C 0.2040(3) 0.1710(3) 0.65546(16) 0.0175(8) Uani 1 1 d . . . H32 H 0.1664 0.0971 0.6596 0.021 Uiso 1 1 calc R . . C33 C 0.2708(3) 0.1773(4) 0.60414(16) 0.0202(8) Uani 1 1 d . . . H33A H 0.3023 0.1037 0.5950 0.024 Uiso 1 1 calc R . . H33B H 0.2213 0.2032 0.5760 0.024 Uiso 1 1 calc R . . C34 C 0.0182(4) 0.2414(5) 0.6324(2) 0.0342(11) Uani 1 1 d . . . H34A H -0.0327 0.3050 0.6370 0.051 Uiso 1 1 calc R . . H34B H -0.0184 0.1740 0.6455 0.051 Uiso 1 1 calc R . . H34C H 0.0351 0.2319 0.5959 0.051 Uiso 1 1 calc R . . O1 O 0.3816(2) 0.2538(2) 0.31604(11) 0.0161(5) Uani 1 1 d . . . O2 O 0.5380(2) 0.1299(2) 0.32098(10) 0.0149(5) Uani 1 1 d . . . O3 O 0.1894(2) 0.1887(2) 0.41628(11) 0.0206(6) Uani 1 1 d . . . O4 O 0.3798(2) 0.2848(2) 0.47922(11) 0.0175(6) Uani 1 1 d . . . O5 O 0.4250(2) 0.5266(2) 0.47109(12) 0.0248(7) Uani 1 1 d . . . O6 O 0.4915(2) 0.2208(2) 0.76713(11) 0.0176(6) Uani 1 1 d . . . O7 O 0.6014(2) 0.3842(2) 0.75542(11) 0.0188(6) Uani 1 1 d . . . O8 O 0.5075(3) 0.0643(2) 0.64966(13) 0.0259(7) Uani 1 1 d . . . O9 O 0.3618(2) 0.2575(2) 0.61381(11) 0.0191(6) Uani 1 1 d . . . O10 O 0.1232(2) 0.2612(3) 0.66051(12) 0.0241(7) Uani 1 1 d . . . Cl1 Cl 0.60729(8) 0.32889(8) 0.39664(4) 0.01924(19) Uani 1 1 d . . . Cl3 Cl 0.71642(8) 0.13119(8) 0.71309(4) 0.0230(2) Uani 1 1 d . . . Cl4 Cl 0.35825(8) 0.45158(8) 0.71136(5) 0.0245(2) Uani 1 1 d . . . Cl2 Cl 0.26710(8) 0.01325(8) 0.33738(4) 0.02031(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0128(17) 0.0175(18) 0.0133(18) -0.0026(15) -0.0028(13) -0.0053(14) C2 0.0102(16) 0.0153(17) 0.0159(18) -0.0044(15) -0.0024(14) -0.0003(13) C3 0.0138(17) 0.0154(17) 0.0171(19) -0.0027(15) 0.0015(14) 0.0028(14) C4 0.0125(16) 0.0120(16) 0.020(2) -0.0020(16) 0.0046(14) -0.0049(13) C5 0.0167(18) 0.0135(17) 0.019(2) 0.0002(15) 0.0028(14) 0.0012(14) C6 0.0160(17) 0.0159(17) 0.015(2) 0.0050(15) 0.0019(13) 0.0025(13) C7 0.0115(16) 0.0142(16) 0.0107(18) -0.0020(14) 0.0039(12) 0.0017(13) C8 0.0180(19) 0.024(2) 0.021(2) -0.0088(17) 0.0041(16) -0.0006(16) C9 0.024(2) 0.022(2) 0.020(2) 0.0039(17) 0.0029(17) -0.0029(16) C10 0.0223(19) 0.0208(19) 0.0148(19) 0.0023(16) -0.0078(15) -0.0032(16) C11 0.027(2) 0.019(2) 0.028(2) 0.0053(18) 0.0012(17) 0.0031(17) C12 0.022(2) 0.0204(19) 0.022(2) -0.0005(17) -0.0018(16) 0.0049(16) C13 0.0188(18) 0.0175(18) 0.0167(19) -0.0048(16) -0.0026(15) 0.0033(14) C14 0.0229(19) 0.0142(17) 0.0143(19) -0.0006(15) -0.0023(14) 0.0051(14) C15 0.0191(18) 0.0190(18) 0.019(2) -0.0030(16) -0.0022(15) 0.0042(15) C16 0.0156(17) 0.024(2) 0.020(2) -0.0035(17) -0.0034(15) 0.0054(16) C17 0.046(3) 0.028(2) 0.041(3) 0.004(2) -0.009(2) -0.011(2) C18 0.0126(17) 0.0117(16) 0.026(2) 0.0018(16) 0.0007(15) 0.0051(13) C19 0.0108(16) 0.0197(18) 0.022(2) 0.0059(17) 0.0014(14) -0.0023(14) C20 0.0141(17) 0.0172(17) 0.0146(19) 0.0018(15) -0.0018(14) -0.0031(14) C21 0.0175(18) 0.0124(17) 0.0176(19) 0.0047(15) -0.0060(14) 0.0032(14) C22 0.0186(18) 0.0145(17) 0.0117(18) 0.0019(15) -0.0012(14) -0.0032(14) C23 0.0188(18) 0.0162(18) 0.0091(17) -0.0015(14) 0.0021(13) -0.0008(14) C24 0.0196(18) 0.0128(17) 0.0142(18) 0.0005(14) -0.0021(14) -0.0020(14) C25 0.0184(19) 0.031(2) 0.016(2) -0.0006(18) -0.0031(15) -0.0036(17) C26 0.0194(19) 0.038(2) 0.020(2) -0.0026(19) -0.0015(16) -0.0051(18) C27 0.026(2) 0.033(2) 0.025(2) 0.0160(19) -0.0086(17) -0.0087(18) C28 0.029(2) 0.040(3) 0.027(2) 0.019(2) -0.0104(18) -0.017(2) C29 0.040(3) 0.039(3) 0.010(2) -0.0002(19) 0.0024(17) -0.018(2) C30 0.026(2) 0.026(2) 0.014(2) 0.0008(17) 0.0035(16) -0.0060(17) C31 0.0136(17) 0.0193(19) 0.021(2) 0.0033(16) 0.0001(14) -0.0031(14) C32 0.0194(18) 0.0152(18) 0.018(2) 0.0030(16) 0.0013(15) -0.0019(14) C33 0.019(2) 0.024(2) 0.017(2) -0.0010(16) 0.0028(15) -0.0045(16) C34 0.023(2) 0.039(3) 0.040(3) 0.003(2) -0.014(2) 0.005(2) O1 0.0158(12) 0.0167(13) 0.0157(13) 0.0020(11) -0.0005(10) 0.0005(10) O2 0.0128(12) 0.0183(13) 0.0135(13) -0.0034(11) 0.0020(10) 0.0012(10) O3 0.0158(13) 0.0258(15) 0.0201(14) 0.0027(12) 0.0016(11) 0.0003(11) O4 0.0236(14) 0.0170(13) 0.0118(13) -0.0020(11) 0.0005(11) 0.0064(11) O5 0.0261(15) 0.0224(15) 0.0258(16) -0.0033(13) -0.0066(12) -0.0001(12) O6 0.0182(13) 0.0211(14) 0.0136(14) 0.0051(11) 0.0017(10) -0.0028(11) O7 0.0188(14) 0.0196(14) 0.0180(14) -0.0014(12) -0.0040(11) -0.0025(11) O8 0.0264(16) 0.0130(14) 0.0382(19) -0.0032(13) 0.0003(14) -0.0003(11) O9 0.0163(14) 0.0236(14) 0.0174(14) 0.0043(12) -0.0041(11) -0.0071(11) O10 0.0168(14) 0.0234(15) 0.0322(18) -0.0056(14) -0.0057(12) 0.0031(11) Cl1 0.0164(4) 0.0195(4) 0.0218(5) -0.0022(4) -0.0007(4) -0.0074(3) Cl3 0.0198(4) 0.0209(4) 0.0284(5) 0.0045(4) -0.0030(4) 0.0068(3) Cl4 0.0189(4) 0.0171(4) 0.0375(6) -0.0029(5) -0.0007(4) 0.0051(3) Cl2 0.0179(4) 0.0210(4) 0.0220(5) -0.0035(4) -0.0017(4) -0.0077(4) _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 C6 1.514(5) . ? C1 C2 1.561(5) . ? C1 C7 1.568(5) . ? C1 Cl2 1.762(4) . ? C2 C10 1.522(5) . ? C2 C3 1.560(5) . ? C3 C13 1.523(5) . ? C3 C4 1.554(5) . ? C4 C5 1.556(5) . ? C4 C7 1.577(5) . ? C4 Cl1 1.778(3) . ? C5 O4 1.418(5) . ? C5 C6 1.541(5) . ? C5 C14 1.551(5) . ? C6 O3 1.214(4) . ? C7 O2 1.377(4) . ? C7 O1 1.408(4) . ? C8 O2 1.435(5) . ? C9 O1 1.442(5) . ? C10 C11 1.536(6) . ? C11 C12 1.538(6) . ? C12 C13 1.536(6) . ? C14 C15 1.526(5) . ? C15 O5 1.422(5) . ? C15 C16 1.502(6) . ? C16 O4 1.438(5) . ? C17 O5 1.401(6) . ? C18 C19 1.539(5) . ? C18 C23 1.544(5) . ? C18 C24 1.575(5) . ? C18 Cl4 1.780(4) . ? C19 C27 1.532(6) . ? C19 C20 1.567(5) . ? C20 C30 1.527(6) . ? C20 C21 1.541(5) . ? C21 C22 1.525(5) . ? C21 C24 1.559(5) . ? C21 Cl3 1.764(4) . ? C22 O8 1.193(5) . ? C22 C23 1.556(5) . ? C23 O9 1.420(4) . ? C23 C31 1.556(5) . ? C24 O7 1.391(5) . ? C24 O6 1.398(4) . ? C25 O7 1.439(5) . ? C26 O6 1.430(5) . ? C27 C28 1.508(6) . ? C28 C29 1.545(7) . ? C29 C30 1.535(6) . ? C31 C32 1.524(5) . ? C32 O10 1.420(5) . ? C32 C33 1.525(5) . ? C33 O9 1.436(5) . ? C34 O10 1.431(5) . ? 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 C6 C1 C2 107.6(3) . . ? C6 C1 C7 99.3(3) . . ? C2 C1 C7 103.1(3) . . ? C6 C1 Cl2 112.3(3) . . ? C2 C1 Cl2 113.7(3) . . ? C7 C1 Cl2 119.3(3) . . ? C10 C2 C3 112.0(3) . . ? C10 C2 C1 114.8(3) . . ? C3 C2 C1 103.1(3) . . ? C13 C3 C4 120.6(3) . . ? C13 C3 C2 113.2(3) . . ? C4 C3 C2 102.9(3) . . ? C3 C4 C5 113.5(3) . . ? C3 C4 C7 100.9(3) . . ? C5 C4 C7 101.0(3) . . ? C3 C4 Cl1 110.8(2) . . ? C5 C4 Cl1 113.8(3) . . ? C7 C4 Cl1 115.9(3) . . ? O4 C5 C6 109.2(3) . . ? O4 C5 C14 105.8(3) . . ? C6 C5 C14 111.6(3) . . ? O4 C5 C4 112.7(3) . . ? C6 C5 C4 100.0(3) . . ? C14 C5 C4 117.4(3) . . ? O3 C6 C1 127.8(3) . . ? O3 C6 C5 124.7(3) . . ? C1 C6 C5 107.5(3) . . ? O2 C7 O1 113.4(3) . . ? O2 C7 C1 117.9(3) . . ? O1 C7 C1 106.0(3) . . ? O2 C7 C4 109.5(3) . . ? O1 C7 C4 116.3(3) . . ? C1 C7 C4 92.3(3) . . ? C2 C10 C11 111.5(3) . . ? C10 C11 C12 112.4(3) . . ? C13 C12 C11 112.3(3) . . ? C3 C13 C12 108.6(3) . . ? C15 C14 C5 104.5(3) . . ? O5 C15 C16 107.4(3) . . ? O5 C15 C14 112.6(3) . . ? C16 C15 C14 102.2(3) . . ? O4 C16 C15 104.4(3) . . ? C19 C18 C23 114.6(3) . . ? C19 C18 C24 99.9(3) . . ? C23 C18 C24 101.3(3) . . ? C19 C18 Cl4 111.2(3) . . ? C23 C18 Cl4 113.5(3) . . ? C24 C18 Cl4 115.2(3) . . ? C27 C19 C18 120.8(3) . . ? C27 C19 C20 111.0(3) . . ? C18 C19 C20 103.6(3) . . ? C30 C20 C21 115.4(3) . . ? C30 C20 C19 112.6(3) . . ? C21 C20 C19 102.4(3) . . ? C22 C21 C20 108.8(3) . . ? C22 C21 C24 100.3(3) . . ? C20 C21 C24 102.2(3) . . ? C22 C21 Cl3 111.7(3) . . ? C20 C21 Cl3 114.0(3) . . ? C24 C21 Cl3 118.5(3) . . ? O8 C22 C21 127.8(4) . . ? O8 C22 C23 125.6(4) . . ? C21 C22 C23 106.6(3) . . ? O9 C23 C18 112.4(3) . . ? O9 C23 C31 105.6(3) . . ? C18 C23 C31 118.3(3) . . ? O9 C23 C22 109.7(3) . . ? C18 C23 C22 100.0(3) . . ? C31 C23 C22 110.8(3) . . ? O7 C24 O6 113.2(3) . . ? O7 C24 C21 116.7(3) . . ? O6 C24 C21 106.7(3) . . ? O7 C24 C18 108.7(3) . . ? O6 C24 C18 117.7(3) . . ? C21 C24 C18 92.4(3) . . ? C28 C27 C19 107.8(3) . . ? C27 C28 C29 111.6(4) . . ? C30 C29 C28 112.1(4) . . ? C20 C30 C29 110.2(3) . . ? C32 C31 C23 105.5(3) . . ? O10 C32 C31 108.3(3) . . ? O10 C32 C33 112.1(3) . . ? C31 C32 C33 102.4(3) . . ? O9 C33 C32 104.8(3) . . ? C7 O1 C9 116.5(3) . . ? C7 O2 C8 115.6(3) . . ? C5 O4 C16 107.6(3) . . ? C17 O5 C15 112.9(3) . . ? C24 O6 C26 117.5(3) . . ? C24 O7 C25 116.7(3) . . ? C23 O9 C33 108.3(3) . . ? C32 O10 C34 113.1(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.486 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.104 # = = = END data_compound_10c _database_code_depnum_ccdc_archive 'CCDC 649157' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H22 Cl2 O7' _chemical_formula_sum 'C16 H22 Cl2 O7' _chemical_formula_weight 397.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.2163(7) _cell_length_b 8.1296(7) _cell_length_c 26.697(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.502(2) _cell_angle_gamma 90.00 _cell_volume 1777.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2818 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 28.21 _exptl_crystal_description Prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9277 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ? _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'CCD area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 11386 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 28.31 _reflns_number_total 4356 _reflns_number_gt 3437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0905P)^2^+4.9203P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4356 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0870 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.2155 _refine_ls_wR_factor_gt 0.1500 _refine_ls_goodness_of_fit_ref 1.168 _refine_ls_restrained_S_all 1.168 _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 0.4020(4) 0.1899(4) 0.37725(13) 0.0177(7) Uani 1 1 d . . . C2 C 0.4959(4) 0.2513(4) 0.42532(13) 0.0167(7) Uani 1 1 d . . . H2 H 0.4221 0.2802 0.4511 0.020 Uiso 1 1 calc R . . C3 C 0.6072(4) 0.1048(4) 0.44197(12) 0.0146(6) Uani 1 1 d . . . H3 H 0.5781 0.0612 0.4743 0.018 Uiso 1 1 calc R . . C4 C 0.5713(4) -0.0241(4) 0.39958(13) 0.0177(7) Uani 1 1 d . . . C5 C 0.6339(4) 0.0281(5) 0.34909(13) 0.0181(7) Uani 1 1 d . . . C6 C 0.5251(4) 0.1787(5) 0.33673(13) 0.0188(7) Uani 1 1 d . . . C7 C 0.3804(4) 0.0046(4) 0.39006(12) 0.0165(7) Uani 1 1 d . . . C8 C 0.2632(5) -0.2437(5) 0.35167(17) 0.0277(9) Uani 1 1 d . . . H8A H 0.2089 -0.2803 0.3205 0.042 Uiso 1 1 calc R . . H8B H 0.1932 -0.2606 0.3784 0.042 Uiso 1 1 calc R . . H8C H 0.3623 -0.3050 0.3585 0.042 Uiso 1 1 calc R . . C9 C 0.1411(5) 0.0087(5) 0.43713(15) 0.0269(9) Uani 1 1 d . . . H9A H 0.1073 -0.0221 0.4694 0.040 Uiso 1 1 calc R . . H9B H 0.0769 -0.0498 0.4113 0.040 Uiso 1 1 calc R . . H9C H 0.1260 0.1249 0.4323 0.040 Uiso 1 1 calc R . . C10 C 0.7518(4) 0.3463(4) 0.44667(13) 0.0187(7) Uani 1 1 d . . . C11 C 0.7407(5) 0.4073(5) 0.49999(14) 0.0242(8) Uani 1 1 d . . . H11A H 0.8408 0.3832 0.5196 0.036 Uiso 1 1 calc R . . H11B H 0.6518 0.3532 0.5145 0.036 Uiso 1 1 calc R . . H11C H 0.7225 0.5239 0.4996 0.036 Uiso 1 1 calc R . . C12 C 0.8922(5) 0.4180(5) 0.42105(16) 0.0262(8) Uani 1 1 d . . . H12A H 0.9925 0.3956 0.4408 0.039 Uiso 1 1 calc R . . H12B H 0.8778 0.5347 0.4176 0.039 Uiso 1 1 calc R . . H12C H 0.8958 0.3693 0.3884 0.039 Uiso 1 1 calc R . . C13 C 0.6108(4) -0.1009(5) 0.30586(14) 0.0225(8) Uani 1 1 d . . . H13A H 0.5740 -0.2054 0.3184 0.027 Uiso 1 1 calc R . . H13B H 0.5320 -0.0625 0.2795 0.027 Uiso 1 1 calc R . . C14 C 0.7814(5) -0.1179(5) 0.28626(14) 0.0228(8) Uani 1 1 d . . . H14 H 0.7736 -0.1214 0.2495 0.027 Uiso 1 1 calc R . . C15 C 0.8667(5) 0.0371(5) 0.30521(14) 0.0237(8) Uani 1 1 d . . . H15A H 0.9839 0.0204 0.3096 0.028 Uiso 1 1 calc R . . H15B H 0.8441 0.1272 0.2819 0.028 Uiso 1 1 calc R . . C16 C 0.8083(6) -0.4087(6) 0.28812(18) 0.0341(10) Uani 1 1 d . . . H16A H 0.8729 -0.4964 0.3033 0.051 Uiso 1 1 calc R . . H16B H 0.8132 -0.4124 0.2523 0.051 Uiso 1 1 calc R . . H16C H 0.6971 -0.4209 0.2961 0.051 Uiso 1 1 calc R . . O1 O 0.3013(3) -0.0703(3) 0.34813(9) 0.0200(6) Uani 1 1 d . . . O2 O 0.3116(3) -0.0317(3) 0.43453(9) 0.0178(5) Uani 1 1 d . . . O3 O 0.5326(3) 0.2707(4) 0.30144(10) 0.0260(6) Uani 1 1 d . . . O4 O 0.6037(3) 0.3808(3) 0.41663(9) 0.0194(5) Uani 1 1 d . . . O5 O 0.7672(3) 0.1705(3) 0.44636(9) 0.0171(5) Uani 1 1 d . . . O6 O 0.8014(3) 0.0708(3) 0.35261(9) 0.0202(6) Uani 1 1 d . . . O7 O 0.8699(4) -0.2557(4) 0.30666(11) 0.0285(6) Uani 1 1 d . . . Cl1 Cl 0.63155(11) -0.22351(11) 0.41977(4) 0.0234(2) Uani 1 1 d . . . Cl2 Cl 0.22767(11) 0.30579(11) 0.35756(3) 0.0213(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0184(17) 0.0175(17) 0.0175(16) 0.0014(13) 0.0030(13) 0.0017(13) C2 0.0186(17) 0.0153(17) 0.0165(16) 0.0011(12) 0.0044(13) 0.0043(13) C3 0.0136(15) 0.0139(16) 0.0158(15) 0.0009(12) -0.0025(12) 0.0019(12) C4 0.0211(18) 0.0133(16) 0.0187(16) -0.0021(13) 0.0012(13) -0.0015(13) C5 0.0153(16) 0.0209(18) 0.0181(16) -0.0053(13) 0.0010(13) -0.0021(13) C6 0.0182(17) 0.0222(18) 0.0158(16) -0.0017(13) -0.0002(13) -0.0028(14) C7 0.0178(17) 0.0168(17) 0.0147(15) 0.0020(12) -0.0006(12) 0.0046(13) C8 0.024(2) 0.020(2) 0.039(2) -0.0016(16) 0.0003(17) -0.0032(15) C9 0.024(2) 0.032(2) 0.0253(19) 0.0076(16) 0.0054(15) 0.0062(16) C10 0.0200(18) 0.0141(17) 0.0217(17) -0.0021(13) -0.0004(14) 0.0032(13) C11 0.033(2) 0.0180(18) 0.0203(17) -0.0085(14) -0.0068(15) 0.0035(15) C12 0.024(2) 0.0180(19) 0.037(2) -0.0011(15) 0.0053(16) 0.0032(15) C13 0.0149(17) 0.030(2) 0.0223(18) -0.0076(15) -0.0006(13) 0.0011(15) C14 0.0217(19) 0.030(2) 0.0176(16) -0.0044(14) 0.0072(14) 0.0059(15) C15 0.0196(18) 0.030(2) 0.0225(18) -0.0019(15) 0.0066(14) -0.0004(15) C16 0.037(2) 0.028(2) 0.036(2) -0.0039(18) -0.0026(19) 0.0020(18) O1 0.0205(13) 0.0201(13) 0.0191(12) -0.0031(10) -0.0009(10) -0.0037(10) O2 0.0165(12) 0.0203(13) 0.0166(11) 0.0023(9) 0.0019(9) -0.0007(10) O3 0.0237(14) 0.0343(16) 0.0201(13) 0.0084(11) 0.0014(11) -0.0007(12) O4 0.0192(13) 0.0157(13) 0.0227(13) 0.0032(10) -0.0019(10) 0.0016(10) O5 0.0176(12) 0.0138(12) 0.0195(12) -0.0010(9) -0.0005(9) 0.0033(9) O6 0.0158(12) 0.0260(14) 0.0192(12) -0.0045(10) 0.0032(10) 0.0020(10) O7 0.0258(15) 0.0329(16) 0.0264(14) -0.0025(12) 0.0002(11) 0.0043(12) Cl1 0.0238(5) 0.0141(4) 0.0319(5) 0.0020(3) 0.0002(4) 0.0035(3) Cl2 0.0181(4) 0.0223(5) 0.0231(4) 0.0047(3) -0.0003(3) 0.0041(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 C2 1.528(5) . ? C1 C6 1.541(5) . ? C1 C7 1.558(5) . ? C1 Cl2 1.760(4) . ? C2 O4 1.407(4) . ? C2 C3 1.545(5) . ? C3 O5 1.416(4) . ? C3 C4 1.553(5) . ? C4 C5 1.540(5) . ? C4 C7 1.587(5) . ? C4 Cl1 1.766(4) . ? C5 O6 1.416(4) . ? C5 C6 1.536(5) . ? C5 C13 1.560(5) . ? C6 O3 1.208(4) . ? C7 O2 1.386(4) . ? C7 O1 1.390(4) . ? C8 O1 1.448(5) . ? C9 O2 1.446(5) . ? C10 O4 1.432(4) . ? C10 O5 1.435(4) . ? C10 C12 1.504(5) . ? C10 C11 1.517(5) . ? C13 C14 1.541(5) . ? C14 O7 1.421(5) . ? C14 C15 1.509(6) . ? C15 O6 1.439(4) . ? C16 O7 1.418(5) . ? 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 C2 C1 C6 107.0(3) . . ? C2 C1 C7 101.0(3) . . ? C6 C1 C7 100.9(3) . . ? C2 C1 Cl2 114.9(2) . . ? C6 C1 Cl2 112.7(2) . . ? C7 C1 Cl2 118.6(3) . . ? O4 C2 C1 112.9(3) . . ? O4 C2 C3 105.0(3) . . ? C1 C2 C3 103.8(3) . . ? O5 C3 C2 104.9(3) . . ? O5 C3 C4 115.9(3) . . ? C2 C3 C4 103.7(3) . . ? C5 C4 C3 113.2(3) . . ? C5 C4 C7 102.3(3) . . ? C3 C4 C7 98.4(3) . . ? C5 C4 Cl1 114.6(3) . . ? C3 C4 Cl1 111.4(2) . . ? C7 C4 Cl1 115.7(2) . . ? O6 C5 C6 111.4(3) . . ? O6 C5 C4 113.5(3) . . ? C6 C5 C4 100.3(3) . . ? O6 C5 C13 106.0(3) . . ? C6 C5 C13 110.0(3) . . ? C4 C5 C13 115.6(3) . . ? O3 C6 C5 126.6(3) . . ? O3 C6 C1 125.9(3) . . ? C5 C6 C1 107.4(3) . . ? O2 C7 O1 113.6(3) . . ? O2 C7 C1 117.0(3) . . ? O1 C7 C1 107.5(3) . . ? O2 C7 C4 107.2(3) . . ? O1 C7 C4 117.3(3) . . ? C1 C7 C4 92.8(3) . . ? O4 C10 O5 105.2(3) . . ? O4 C10 C12 108.5(3) . . ? O5 C10 C12 108.2(3) . . ? O4 C10 C11 110.5(3) . . ? O5 C10 C11 110.0(3) . . ? C12 C10 C11 113.9(3) . . ? C14 C13 C5 104.5(3) . . ? O7 C14 C15 108.6(3) . . ? O7 C14 C13 113.1(3) . . ? C15 C14 C13 102.9(3) . . ? O6 C15 C14 105.0(3) . . ? C7 O1 C8 117.6(3) . . ? C7 O2 C9 117.0(3) . . ? C2 O4 C10 106.2(3) . . ? C3 O5 C10 107.1(3) . . ? C5 O6 C15 108.8(3) . . ? C16 O7 C14 113.6(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.674 _refine_diff_density_min -0.685 _refine_diff_density_rms 0.150 # = = = END data_compound_13c _database_code_depnum_ccdc_archive 'CCDC 649158' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H22 Cl2 O6' _chemical_formula_sum 'C15 H22 Cl2 O6' _chemical_formula_weight 369.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 34.375(2) _cell_length_b 34.375(2) _cell_length_c 7.2354(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 7404.0(9) _cell_formula_units_Z 18 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7082 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 28.32 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3492 _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9739 _exptl_absorpt_process_details SADABS _exptl_special_details ? _diffrn_ambient_temperature 100(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 'CCD area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 16448 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.35 _reflns_number_total 4096 _reflns_number_gt 3504 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0893P)^2^+45.6370P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4096 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0475 _refine_ls_wR_factor_ref 0.1817 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.88799(2) 0.03609(2) 0.08629(9) 0.0219(2) Uani 1 1 d . . . Cl2 Cl 0.81235(2) 0.11727(2) 0.51653(9) 0.0210(2) Uani 1 1 d . . . O4 O 0.80627(7) -0.02713(7) 0.3012(3) 0.0204(4) Uani 1 1 d . . . O2 O 0.88594(7) 0.13135(7) 0.2221(3) 0.0209(4) Uani 1 1 d . . . O3 O 0.90118(7) 0.03575(7) 0.5308(3) 0.0185(4) Uani 1 1 d . . . O5 O 0.75722(6) 0.02181(6) 0.3840(3) 0.0172(4) Uani 1 1 d . . . O1 O 0.82075(7) 0.07160(6) 0.1007(3) 0.0167(4) Uani 1 1 d . . . O6 O 0.71320(7) -0.00646(7) 0.7696(3) 0.0192(4) Uani 1 1 d . . . C15 C 0.71599(10) -0.01421(10) 0.9624(4) 0.0199(6) Uani 1 1 d . . . H15A H 0.6999 -0.0030 1.0323 0.030 Uiso 1 1 calc R . . H15B H 0.7469 0.0011 1.0000 0.030 Uiso 1 1 calc R . . H15C H 0.7030 -0.0459 0.9840 0.030 Uiso 1 1 calc R . . C12 C 0.78768(9) 0.01008(9) 0.6595(4) 0.0172(5) Uani 1 1 d . . . H12A H 0.7959 0.0329 0.7539 0.021 Uiso 1 1 calc R . . H12B H 0.8034 -0.0063 0.6830 0.021 Uiso 1 1 calc R . . C4 C 0.83353(9) 0.08180(9) 0.4477(4) 0.0158(5) Uani 1 1 d . . . C5 C 0.79872(9) 0.03127(9) 0.4650(4) 0.0144(5) Uani 1 1 d . . . C6 C 0.82159(9) 0.01181(9) 0.3422(4) 0.0148(5) Uani 1 1 d . . . C13 C 0.73631(9) -0.02208(9) 0.6560(4) 0.0160(5) Uani 1 1 d . . . H13 H 0.7289 -0.0525 0.6915 0.019 Uiso 1 1 calc R . . C1 C 0.86616(9) 0.05133(9) 0.2756(4) 0.0178(5) Uani 1 1 d . . . C14 C 0.72347(9) -0.02085(10) 0.4551(4) 0.0197(6) Uani 1 1 d . . . H14A H 0.7230 -0.0452 0.3855 0.024 Uiso 1 1 calc R . . H14B H 0.6940 -0.0236 0.4478 0.024 Uiso 1 1 calc R . . C11 C 0.94070(11) 0.01452(11) 0.7429(4) 0.0252(6) Uani 1 1 d . . . H11A H 0.9648 0.0257 0.8311 0.038 Uiso 1 1 calc R . . H11B H 0.9464 -0.0010 0.6460 0.038 Uiso 1 1 calc R . . H11C H 0.9130 -0.0058 0.8034 0.038 Uiso 1 1 calc R . . C7 C 0.85137(9) 0.08717(9) 0.2450(4) 0.0163(5) Uani 1 1 d . . . C10 C 0.93746(10) 0.05326(10) 0.6617(4) 0.0202(6) Uani 1 1 d . . . H10A H 0.9320 0.0693 0.7590 0.024 Uiso 1 1 calc R . . H10B H 0.9654 0.0740 0.6008 0.024 Uiso 1 1 calc R . . C2 C 0.89797(9) 0.07074(9) 0.4415(4) 0.0180(5) Uani 1 1 d . . . H2 H 0.9277 0.0941 0.3999 0.022 Uiso 1 1 calc R . . C3 C 0.87578(9) 0.09204(9) 0.5586(4) 0.0176(5) Uani 1 1 d . . . H3A H 0.8679 0.0786 0.6805 0.021 Uiso 1 1 calc R . . H3B H 0.8957 0.1242 0.5716 0.021 Uiso 1 1 calc R . . C9 C 0.79788(11) 0.09631(10) 0.0651(4) 0.0230(6) Uani 1 1 d . . . H9A H 0.7776 0.0829 -0.0368 0.034 Uiso 1 1 calc R . . H9B H 0.8195 0.1269 0.0355 0.034 Uiso 1 1 calc R . . H9C H 0.7813 0.0956 0.1730 0.034 Uiso 1 1 calc R . . C8 C 0.90890(11) 0.14155(11) 0.0471(4) 0.0287(7) Uani 1 1 d . . . H8A H 0.9319 0.1726 0.0447 0.043 Uiso 1 1 calc R . . H8B H 0.8878 0.1358 -0.0507 0.043 Uiso 1 1 calc R . . H8C H 0.9223 0.1230 0.0306 0.043 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 Cl1 0.0227(4) 0.0269(4) 0.0165(3) -0.0030(2) 0.0040(2) 0.0127(3) Cl2 0.0290(4) 0.0198(3) 0.0189(3) -0.0024(2) 0.0008(3) 0.0158(3) O4 0.0214(10) 0.0153(9) 0.0225(10) -0.0005(8) -0.0012(8) 0.0076(8) O2 0.0222(10) 0.0131(9) 0.0169(10) 0.0016(7) 0.0030(8) 0.0010(8) O3 0.0168(9) 0.0176(9) 0.0202(10) -0.0019(7) -0.0026(7) 0.0080(8) O5 0.0138(9) 0.0175(9) 0.0171(9) 0.0031(7) -0.0005(7) 0.0055(8) O1 0.0197(9) 0.0139(9) 0.0134(9) -0.0010(7) -0.0012(7) 0.0060(8) O6 0.0200(10) 0.0262(10) 0.0163(9) 0.0009(8) 0.0013(7) 0.0154(9) C15 0.0191(13) 0.0234(14) 0.0160(13) 0.0008(10) 0.0023(10) 0.0098(11) C12 0.0165(12) 0.0186(13) 0.0149(12) 0.0024(10) 0.0002(10) 0.0076(10) C4 0.0178(12) 0.0131(12) 0.0147(12) -0.0012(9) 0.0012(9) 0.0064(10) C5 0.0143(12) 0.0152(12) 0.0154(12) 0.0011(9) -0.0001(9) 0.0087(10) C6 0.0167(12) 0.0153(12) 0.0125(11) 0.0004(9) -0.0025(9) 0.0079(10) C13 0.0157(12) 0.0179(12) 0.0171(12) 0.0012(10) 0.0026(10) 0.0103(10) C1 0.0191(13) 0.0190(13) 0.0139(12) -0.0001(10) 0.0034(10) 0.0084(11) C14 0.0171(13) 0.0204(13) 0.0177(13) 0.0008(10) -0.0009(10) 0.0064(11) C11 0.0280(15) 0.0279(15) 0.0220(14) -0.0021(12) -0.0036(12) 0.0157(13) C7 0.0182(12) 0.0126(12) 0.0130(12) -0.0024(9) 0.0007(9) 0.0039(10) C10 0.0180(13) 0.0225(14) 0.0175(13) -0.0024(10) -0.0021(10) 0.0082(11) C2 0.0155(12) 0.0172(12) 0.0168(12) -0.0014(10) 0.0007(10) 0.0049(10) C3 0.0167(12) 0.0186(13) 0.0156(12) 0.0007(10) 0.0000(10) 0.0073(11) C9 0.0310(16) 0.0223(14) 0.0179(13) 0.0010(11) -0.0008(11) 0.0149(13) C8 0.0306(16) 0.0215(14) 0.0186(14) 0.0014(11) 0.0066(12) 0.0014(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.763(3) . ? Cl2 C4 1.775(3) . ? O4 C6 1.205(3) . ? O2 C7 1.393(3) . ? O2 C8 1.440(4) . ? O3 C2 1.417(3) . ? O3 C10 1.437(3) . ? O5 C5 1.421(3) . ? O5 C14 1.435(3) . ? O1 C7 1.386(3) . ? O1 C9 1.440(4) . ? O6 C13 1.422(3) . ? O6 C15 1.432(3) . ? C12 C5 1.542(4) . ? C12 C13 1.545(4) . ? C4 C3 1.538(4) . ? C4 C5 1.545(4) . ? C4 C7 1.564(4) . ? C5 C6 1.543(4) . ? C6 C1 1.531(4) . ? C13 C14 1.525(4) . ? C1 C2 1.534(4) . ? C1 C7 1.566(4) . ? C11 C10 1.509(4) . ? C2 C3 1.547(4) . ? 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 C7 O2 C8 115.8(2) . . ? C2 O3 C10 111.4(2) . . ? C5 O5 C14 107.0(2) . . ? C7 O1 C9 116.1(2) . . ? C13 O6 C15 113.0(2) . . ? C5 C12 C13 104.3(2) . . ? C3 C4 C5 109.1(2) . . ? C3 C4 C7 101.1(2) . . ? C5 C4 C7 104.3(2) . . ? C3 C4 Cl2 111.17(18) . . ? C5 C4 Cl2 113.36(18) . . ? C7 C4 Cl2 116.95(19) . . ? O5 C5 C12 106.6(2) . . ? O5 C5 C6 109.5(2) . . ? C12 C5 C6 112.3(2) . . ? O5 C5 C4 110.4(2) . . ? C12 C5 C4 118.3(2) . . ? C6 C5 C4 99.5(2) . . ? O4 C6 C1 126.6(3) . . ? O4 C6 C5 126.1(2) . . ? C1 C6 C5 107.3(2) . . ? O6 C13 C14 108.4(2) . . ? O6 C13 C12 112.0(2) . . ? C14 C13 C12 103.8(2) . . ? C6 C1 C2 108.6(2) . . ? C6 C1 C7 99.7(2) . . ? C2 C1 C7 102.1(2) . . ? C6 C1 Cl1 111.52(19) . . ? C2 C1 Cl1 114.87(19) . . ? C7 C1 Cl1 118.55(19) . . ? O5 C14 C13 105.8(2) . . ? O1 C7 O2 113.6(2) . . ? O1 C7 C4 118.9(2) . . ? O2 C7 C4 108.1(2) . . ? O1 C7 C1 106.6(2) . . ? O2 C7 C1 116.0(2) . . ? C4 C7 C1 92.1(2) . . ? O3 C10 C11 108.6(2) . . ? O3 C2 C1 109.2(2) . . ? O3 C2 C3 114.7(2) . . ? C1 C2 C3 102.8(2) . . ? C4 C3 C2 103.8(2) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.717 _refine_diff_density_min -0.585 _refine_diff_density_rms 0.136 # = = = END data_compound_14d _database_code_depnum_ccdc_archive 'CCDC 649159' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H20 Cl2 O7' _chemical_formula_sum 'C15 H20 Cl2 O7' _chemical_formula_weight 383.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3266(6) _cell_length_b 21.5800(17) _cell_length_c 11.0281(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.9950(10) _cell_angle_gamma 90.00 _cell_volume 1705.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4270 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.24 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.415 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9477 _exptl_absorpt_correction_T_max 0.9739 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ? _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 11005 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4161 _reflns_number_gt 3531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.628 (Bruker, 2003)' _computing_cell_refinement 'SAINT 6.45 (Bruker, 2003)' _computing_data_reduction 'SAINT 6.45 (Bruker, 2003)' _computing_structure_solution SIR-92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0417P)^2^+5.2932P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4161 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1571 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6853(4) 0.81106(13) 0.2332(3) 0.0156(6) Uani 1 1 d . . . C2 C 0.5828(4) 0.77143(13) 0.3135(3) 0.0141(5) Uani 1 1 d . . . H2 H 0.6737 0.7550 0.3842 0.017 Uiso 1 1 calc R . . C3 C 0.4600(4) 0.82089(13) 0.3608(3) 0.0167(6) Uani 1 1 d . . . H3A H 0.3284 0.8124 0.3303 0.020 Uiso 1 1 calc R . . H3B H 0.4853 0.8219 0.4507 0.020 Uiso 1 1 calc R . . C4 C 0.5160(4) 0.88238(13) 0.3082(3) 0.0152(6) Uani 1 1 d . . . C5 C 0.4291(4) 0.88688(13) 0.1689(3) 0.0137(5) Uani 1 1 d . . . C6 C 0.5448(4) 0.83565(14) 0.1210(3) 0.0170(6) Uani 1 1 d . . . C7 C 0.7274(4) 0.87115(14) 0.3135(3) 0.0163(6) Uani 1 1 d . . . C8 C 1.0051(5) 0.84544(17) 0.4650(3) 0.0258(7) Uani 1 1 d . . . H8A H 1.0481 0.8423 0.5531 0.039 Uiso 1 1 calc R . . H8B H 1.0781 0.8759 0.4328 0.039 Uiso 1 1 calc R . . H8C H 1.0181 0.8060 0.4273 0.039 Uiso 1 1 calc R . . C9 C 0.8580(5) 0.97241(15) 0.2975(3) 0.0228(7) Uani 1 1 d . . . H9A H 0.9257 0.9954 0.2467 0.034 Uiso 1 1 calc R . . H9B H 0.9297 0.9706 0.3808 0.034 Uiso 1 1 calc R . . H9C H 0.7410 0.9925 0.2971 0.034 Uiso 1 1 calc R . . C10 C 0.4713(4) 0.71834(14) 0.2460(3) 0.0173(6) Uani 1 1 d . . . C11 C 0.4756(5) 0.61090(15) 0.2108(3) 0.0255(7) Uani 1 1 d . . . H11A H 0.5616 0.5768 0.2220 0.038 Uiso 1 1 calc R . . H11B H 0.4208 0.6154 0.1243 0.038 Uiso 1 1 calc R . . H11C H 0.3793 0.6032 0.2560 0.038 Uiso 1 1 calc R . . C12 C 0.2175(4) 0.87735(14) 0.1330(3) 0.0163(6) Uani 1 1 d . . . H12A H 0.1877 0.8362 0.0991 0.020 Uiso 1 1 calc R . . H12B H 0.1606 0.8828 0.2042 0.020 Uiso 1 1 calc R . . C13 C 0.1506(4) 0.92716(14) 0.0351(3) 0.0198(6) Uani 1 1 d . . . H13 H 0.0264 0.9422 0.0406 0.024 Uiso 1 1 calc R . . C14 C 0.2953(4) 0.97687(14) 0.0729(3) 0.0181(6) Uani 1 1 d . . . H14A H 0.3041 1.0029 0.0026 0.022 Uiso 1 1 calc R . . H14B H 0.2636 1.0027 0.1376 0.022 Uiso 1 1 calc R . . C15 C 0.0228(7) 0.8620(2) -0.1347(4) 0.0427(10) Uani 1 1 d . . . H15A H 0.0328 0.8515 -0.2176 0.064 Uiso 1 1 calc R . . H15B H -0.1009 0.8769 -0.1351 0.064 Uiso 1 1 calc R . . H15C H 0.0472 0.8259 -0.0829 0.064 Uiso 1 1 calc R . . O1 O 0.8242(3) 0.91046(10) 0.2492(2) 0.0163(4) Uani 1 1 d . . . O2 O 0.8125(3) 0.86368(10) 0.4377(2) 0.0183(5) Uani 1 1 d . . . O3 O 0.5258(4) 0.81845(12) 0.0156(2) 0.0264(5) Uani 1 1 d . . . O4 O 0.5735(3) 0.66698(10) 0.2560(2) 0.0206(5) Uani 1 1 d . . . O5 O 0.3127(3) 0.72193(11) 0.1891(3) 0.0300(6) Uani 1 1 d . . . O6 O 0.4685(3) 0.94499(9) 0.1178(2) 0.0166(4) Uani 1 1 d . . . O7 O 0.1549(3) 0.90901(11) -0.0879(2) 0.0255(5) Uani 1 1 d . . . Cl1 Cl 0.45940(11) 0.94731(3) 0.39213(7) 0.01911(18) Uani 1 1 d . . . Cl2 Cl 0.87507(10) 0.77301(3) 0.18759(8) 0.02121(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0172(14) 0.0104(13) 0.0217(14) -0.0011(11) 0.0099(11) 0.0024(11) C2 0.0169(13) 0.0105(13) 0.0157(13) 0.0011(10) 0.0052(11) 0.0000(10) C3 0.0230(15) 0.0110(13) 0.0184(14) 0.0016(11) 0.0092(11) 0.0002(11) C4 0.0218(15) 0.0094(13) 0.0145(13) 0.0001(10) 0.0043(11) 0.0010(11) C5 0.0162(14) 0.0089(13) 0.0160(13) -0.0006(10) 0.0036(10) -0.0017(10) C6 0.0181(14) 0.0138(14) 0.0211(15) -0.0003(11) 0.0083(11) -0.0038(11) C7 0.0181(14) 0.0123(13) 0.0192(14) 0.0014(11) 0.0056(11) 0.0006(11) C8 0.0211(16) 0.0271(18) 0.0271(17) 0.0021(14) 0.0000(13) 0.0065(13) C9 0.0264(17) 0.0144(15) 0.0286(17) -0.0009(13) 0.0079(13) -0.0033(12) C10 0.0248(16) 0.0104(13) 0.0172(14) 0.0012(11) 0.0056(12) -0.0015(11) C11 0.039(2) 0.0115(14) 0.0251(16) -0.0058(12) 0.0036(14) -0.0058(13) C12 0.0154(14) 0.0128(13) 0.0215(15) 0.0028(11) 0.0058(11) -0.0017(10) C13 0.0180(15) 0.0151(14) 0.0250(16) 0.0010(12) 0.0016(12) 0.0005(11) C14 0.0166(14) 0.0132(14) 0.0228(15) 0.0009(11) 0.0003(11) 0.0015(11) C15 0.052(3) 0.037(2) 0.033(2) -0.0042(17) -0.0042(18) -0.019(2) O1 0.0145(10) 0.0117(10) 0.0238(11) 0.0013(8) 0.0066(8) -0.0021(8) O2 0.0167(10) 0.0195(11) 0.0172(10) 0.0008(8) 0.0002(8) -0.0007(8) O3 0.0363(14) 0.0266(13) 0.0171(11) -0.0031(9) 0.0071(10) 0.0077(10) O4 0.0226(11) 0.0109(10) 0.0283(12) -0.0028(9) 0.0056(9) 0.0027(8) O5 0.0244(12) 0.0179(12) 0.0413(15) -0.0021(10) -0.0077(11) -0.0004(10) O6 0.0146(10) 0.0118(10) 0.0234(11) 0.0045(8) 0.0038(8) -0.0024(8) O7 0.0323(13) 0.0230(12) 0.0185(11) -0.0002(9) -0.0007(9) -0.0091(10) Cl1 0.0261(4) 0.0125(3) 0.0201(4) -0.0028(3) 0.0079(3) 0.0014(3) Cl2 0.0197(4) 0.0143(3) 0.0328(4) 0.0017(3) 0.0127(3) 0.0028(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 C6 1.531(4) . ? C1 C2 1.535(4) . ? C1 C7 1.564(4) . ? C1 Cl2 1.775(3) . ? C2 C10 1.511(4) . ? C2 C3 1.554(4) . ? C3 C4 1.538(4) . ? C4 C5 1.539(4) . ? C4 C7 1.557(4) . ? C4 Cl1 1.775(3) . ? C5 O6 1.429(3) . ? C5 C12 1.532(4) . ? C5 C6 1.551(4) . ? C6 O3 1.201(4) . ? C7 O1 1.391(3) . ? C7 O2 1.391(4) . ? C8 O2 1.435(4) . ? C9 O1 1.441(4) . ? C10 O5 1.203(4) . ? C10 O4 1.329(4) . ? C11 O4 1.442(4) . ? C12 C13 1.530(4) . ? C13 O7 1.418(4) . ? C13 C14 1.505(4) . ? C14 O6 1.438(4) . ? C15 O7 1.423(4) . ? 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 C6 C1 C2 109.4(2) . . ? C6 C1 C7 101.0(2) . . ? C2 C1 C7 101.4(2) . . ? C6 C1 Cl2 111.5(2) . . ? C2 C1 Cl2 114.3(2) . . ? C7 C1 Cl2 118.0(2) . . ? C10 C2 C1 114.7(2) . . ? C10 C2 C3 113.3(2) . . ? C1 C2 C3 101.4(2) . . ? C4 C3 C2 104.3(2) . . ? C3 C4 C5 110.1(2) . . ? C3 C4 C7 101.1(2) . . ? C5 C4 C7 104.4(2) . . ? C3 C4 Cl1 112.0(2) . . ? C5 C4 Cl1 112.2(2) . . ? C7 C4 Cl1 116.2(2) . . ? O6 C5 C12 107.0(2) . . ? O6 C5 C4 111.9(2) . . ? C12 C5 C4 115.8(2) . . ? O6 C5 C6 108.8(2) . . ? C12 C5 C6 114.3(2) . . ? C4 C5 C6 98.8(2) . . ? O3 C6 C1 126.8(3) . . ? O3 C6 C5 126.0(3) . . ? C1 C6 C5 107.2(2) . . ? O1 C7 O2 113.6(2) . . ? O1 C7 C4 119.6(2) . . ? O2 C7 C4 107.1(2) . . ? O1 C7 C1 106.2(2) . . ? O2 C7 C1 117.2(2) . . ? C4 C7 C1 91.7(2) . . ? O5 C10 O4 124.3(3) . . ? O5 C10 C2 125.0(3) . . ? O4 C10 C2 110.7(3) . . ? C13 C12 C5 104.3(2) . . ? O7 C13 C14 107.9(3) . . ? O7 C13 C12 114.4(3) . . ? C14 C13 C12 101.6(2) . . ? O6 C14 C13 106.0(2) . . ? C7 O1 C9 116.4(2) . . ? C7 O2 C8 117.3(2) . . ? C10 O4 C11 116.1(3) . . ? C5 O6 C14 108.6(2) . . ? C13 O7 C15 113.3(3) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.644 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.134