data_22 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 Cl4 O5' _chemical_formula_sum 'C12 H12 Cl4 O5' _chemical_formula_weight 378.02 _chemical_absolute_configuration rmad 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 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.3550(7) _cell_length_b 13.6917(12) _cell_length_c 14.3079(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1440.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2667 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 28.25 _exptl_crystal_description 'prism' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.743 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.838 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.9299 _exptl_absorpt_correction_T_max 0.9444 _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 9426 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0526 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3540 _reflns_number_gt 3098 _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^)+(0.0323P)^2^+2.8529P] 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 -0.03(10) _refine_ls_number_reflns 3540 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 0.4237(5) 0.4660(3) 0.1158(3) 0.0190(8) Uani 1 1 d . . . C2 C 0.3159(5) 0.3945(3) 0.0512(3) 0.0188(8) Uani 1 1 d . . . H2 H 0.1875 0.3896 0.0689 0.023 Uiso 1 1 calc R . . C3 C 0.3413(5) 0.4374(3) -0.0480(3) 0.0162(7) Uani 1 1 d . . . H3 H 0.2251 0.4624 -0.0714 0.019 Uiso 1 1 calc R . . C4 C 0.4733(5) 0.5238(3) -0.0276(3) 0.0162(7) Uani 1 1 d . . . C5 C 0.6530(5) 0.4881(3) 0.0113(3) 0.0180(7) Uani 1 1 d . . . C6 C 0.6242(5) 0.4539(3) 0.0977(3) 0.0209(8) Uani 1 1 d . . . C7 C 0.3874(5) 0.5654(3) 0.0653(3) 0.0194(8) Uani 1 1 d . . . C8 C 0.1393(6) 0.6703(3) 0.0220(3) 0.0293(10) Uani 1 1 d . . . H8A H 0.0092 0.6739 0.0265 0.044 Uiso 1 1 calc R . . H8B H 0.1744 0.6699 -0.0426 0.044 Uiso 1 1 calc R . . H8C H 0.1923 0.7259 0.0525 0.044 Uiso 1 1 calc R . . C9 C 0.4548(7) 0.6847(3) 0.1828(3) 0.0318(11) Uani 1 1 d . . . H9A H 0.5332 0.7395 0.1942 0.048 Uiso 1 1 calc R . . H9B H 0.4769 0.6352 0.2289 0.048 Uiso 1 1 calc R . . H9C H 0.3303 0.7054 0.1863 0.048 Uiso 1 1 calc R . . C10 C 0.4078(5) 0.2957(3) 0.0474(3) 0.0199(8) Uani 1 1 d . . . C11 C 0.4005(5) 0.3488(3) -0.1058(3) 0.0195(8) Uani 1 1 d . . . H11 H 0.2907 0.3198 -0.1329 0.023 Uiso 1 1 calc R . . C12 C 0.5354(6) 0.3638(3) -0.1845(3) 0.0225(8) Uani 1 1 d . . . H12A H 0.4861 0.4101 -0.2292 0.027 Uiso 1 1 calc R . . H12B H 0.6472 0.3908 -0.1595 0.027 Uiso 1 1 calc R . . O1 O 0.4906(4) 0.64605(19) 0.09191(18) 0.0196(6) Uani 1 1 d . . . O2 O 0.2025(4) 0.58172(19) 0.0666(2) 0.0212(6) Uani 1 1 d . . . O3 O 0.4298(4) 0.2401(2) 0.1109(2) 0.0259(6) Uani 1 1 d . . . O4 O 0.4751(4) 0.27858(19) -0.03897(19) 0.0210(6) Uani 1 1 d . . . O5 O 0.5730(4) 0.2737(2) -0.2303(2) 0.0295(7) Uani 1 1 d . . . H5 H 0.6453 0.2830 -0.2730 0.044 Uiso 1 1 calc R . . Cl1 Cl 0.49310(14) 0.60880(7) -0.11980(6) 0.0229(2) Uani 1 1 d . . . Cl2 Cl 0.35469(16) 0.45478(7) 0.23355(7) 0.0283(2) Uani 1 1 d . . . Cl3 Cl 0.77670(15) 0.40369(8) 0.17201(8) 0.0321(3) Uani 1 1 d . . . Cl4 Cl 0.85475(14) 0.49306(8) -0.04654(8) 0.0306(3) 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 0.0238(19) 0.0185(18) 0.0148(18) 0.0011(16) 0.0055(16) 0.0016(15) C2 0.0232(19) 0.0157(17) 0.0174(17) 0.0019(16) 0.0010(15) 0.0003(15) C3 0.0151(16) 0.0159(17) 0.0176(17) 0.0038(14) -0.0028(15) -0.0014(14) C4 0.0171(18) 0.0154(17) 0.0163(17) 0.0045(14) -0.0010(14) -0.0013(14) C5 0.0184(17) 0.0187(18) 0.0168(17) -0.0034(15) -0.0026(15) 0.0020(15) C6 0.0222(19) 0.0183(19) 0.0221(19) -0.0047(16) -0.0101(16) 0.0007(16) C7 0.0215(19) 0.0174(17) 0.0192(19) 0.0027(15) -0.0025(15) -0.0020(14) C8 0.022(2) 0.019(2) 0.047(3) -0.0010(19) -0.002(2) 0.0034(17) C9 0.051(3) 0.022(2) 0.023(2) -0.0061(18) 0.006(2) -0.007(2) C10 0.0225(19) 0.0201(19) 0.0172(18) -0.0027(16) -0.0050(16) -0.0019(15) C11 0.023(2) 0.0156(17) 0.0200(19) -0.0031(16) -0.0025(16) -0.0014(14) C12 0.027(2) 0.0210(19) 0.0200(19) -0.0069(16) 0.0058(16) -0.0016(16) O1 0.0274(14) 0.0157(12) 0.0157(13) -0.0043(10) 0.0013(12) -0.0030(11) O2 0.0200(13) 0.0169(14) 0.0267(15) -0.0011(12) 0.0028(11) 0.0040(10) O3 0.0368(16) 0.0178(14) 0.0231(15) 0.0048(12) -0.0014(13) -0.0025(12) O4 0.0257(15) 0.0162(13) 0.0212(14) -0.0027(11) -0.0027(12) 0.0001(11) O5 0.0374(17) 0.0273(16) 0.0237(15) -0.0109(13) 0.0112(14) 0.0005(13) Cl1 0.0349(5) 0.0186(4) 0.0153(4) 0.0020(4) 0.0013(4) -0.0057(4) Cl2 0.0441(6) 0.0252(5) 0.0156(4) 0.0000(4) 0.0048(5) -0.0007(5) Cl3 0.0335(6) 0.0295(6) 0.0333(6) -0.0018(5) -0.0173(5) 0.0049(5) Cl4 0.0171(4) 0.0381(6) 0.0365(6) -0.0102(5) 0.0048(5) -0.0035(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 1.507(6) . ? C1 C2 1.563(5) . ? C1 C7 1.564(5) . ? C1 Cl2 1.766(4) . ? C2 C10 1.514(5) . ? C2 C3 1.547(5) . ? C3 C11 1.531(5) . ? C3 C4 1.558(5) . ? C4 C5 1.515(5) . ? C4 C7 1.578(5) . ? C4 Cl1 1.765(4) . ? C5 C6 1.340(5) . ? C5 Cl4 1.700(4) . ? C6 Cl3 1.691(4) . ? C7 O2 1.378(5) . ? C7 O1 1.393(5) . ? C8 O2 1.447(5) . ? C9 O1 1.429(5) . ? C10 O3 1.196(5) . ? C10 O4 1.351(5) . ? C11 O4 1.463(5) . ? C11 C12 1.514(5) . ? C12 O5 1.425(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 109.0(3) . . ? C6 C1 C7 100.6(3) . . ? C2 C1 C7 100.7(3) . . ? C6 C1 Cl2 115.8(3) . . ? C2 C1 Cl2 111.3(3) . . ? C7 C1 Cl2 117.9(3) . . ? C10 C2 C3 104.6(3) . . ? C10 C2 C1 110.8(3) . . ? C3 C2 C1 104.1(3) . . ? C11 C3 C2 103.3(3) . . ? C11 C3 C4 121.7(3) . . ? C2 C3 C4 101.0(3) . . ? C5 C4 C3 111.6(3) . . ? C5 C4 C7 99.0(3) . . ? C3 C4 C7 100.5(3) . . ? C5 C4 Cl1 114.5(3) . . ? C3 C4 Cl1 114.4(3) . . ? C7 C4 Cl1 115.1(3) . . ? C6 C5 C4 108.3(3) . . ? C6 C5 Cl4 126.9(3) . . ? C4 C5 Cl4 124.8(3) . . ? C5 C6 C1 105.9(3) . . ? C5 C6 Cl3 128.2(3) . . ? C1 C6 Cl3 125.9(3) . . ? O2 C7 O1 113.9(3) . . ? O2 C7 C1 107.7(3) . . ? O1 C7 C1 118.0(3) . . ? O2 C7 C4 117.7(3) . . ? O1 C7 C4 107.3(3) . . ? C1 C7 C4 90.4(3) . . ? O3 C10 O4 122.3(4) . . ? O3 C10 C2 127.0(4) . . ? O4 C10 C2 110.6(3) . . ? O4 C11 C12 109.3(3) . . ? O4 C11 C3 105.9(3) . . ? C12 C11 C3 118.7(3) . . ? O5 C12 C11 110.6(3) . . ? C7 O1 C9 116.2(3) . . ? C7 O2 C8 116.6(3) . . ? C10 O4 C11 110.3(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.495 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.117 # = = = END data_23 _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H9.60 Cl4 O4' _chemical_formula_sum 'C10 H9.60 Cl4 O4' _chemical_formula_weight 335.58 _chemical_absolute_configuration rmad 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 'C121' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 29.003(3) _cell_length_b 8.7758(7) _cell_length_c 13.4454(11) _cell_angle_alpha 90.00 _cell_angle_beta 94.309(3) _cell_angle_gamma 90.00 _cell_volume 3412.5(5) _cell_formula_units_Z 10 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2135 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 24.10 _exptl_crystal_description 'Prism' _exptl_crystal_colour 'Colorless' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.633 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1696 _exptl_absorpt_coefficient_mu 0.868 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.9182 _exptl_absorpt_correction_T_max 0.9259 _exptl_absorpt_process_details 'SADABS 2.10 (Bruker 2003)' _exptl_special_details ? _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area Detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 60 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.5 _diffrn_reflns_number 11378 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0932 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 28.35 _reflns_number_total 7886 _reflns_number_gt 6132 _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^)+(0.0279P)^2^+40.2538P] 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 -0.08(10) _refine_ls_number_reflns 7886 _refine_ls_number_parameters 407 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0984 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.1762 _refine_ls_wR_factor_gt 0.1296 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Cl5 Cl 0.91974(7) 0.0201(2) 0.32487(15) 0.0303(4) Uani 1 1 d . . . Cl1 Cl 0.86827(6) 0.1799(2) 0.00781(14) 0.0251(4) Uani 1 1 d . . . Cl8 Cl 0.88669(7) -0.3336(2) 0.34378(15) 0.0326(4) Uani 1 1 d . . . Cl2 Cl 0.89103(7) 0.7785(2) -0.11494(14) 0.0300(4) Uani 1 1 d . . . Cl6 Cl 0.83475(7) -0.0505(2) 0.68019(13) 0.0315(4) Uani 1 1 d . . . Cl4 Cl 0.91778(6) 0.3721(2) 0.19347(13) 0.0279(4) Uani 1 1 d . . . Cl7 Cl 0.84136(7) -0.3840(2) 0.56674(16) 0.0351(5) Uani 1 1 d . . . Cl3 Cl 0.93785(7) 0.7377(2) 0.11380(15) 0.0314(4) Uani 1 1 d . . . Cl10 Cl 0.99013(9) 0.0617(3) 0.89156(17) 0.0468(6) Uani 1 1 d . . . Cl9 Cl 0.98746(11) 0.5998(4) 0.6024(2) 0.0671(9) Uani 1 1 d . . . O6 O 0.93142(17) -0.0245(6) 0.5529(4) 0.0285(12) Uani 1 1 d . . . O2 O 0.85289(16) 0.4500(6) -0.1760(3) 0.0226(10) Uani 1 1 d . . . O5 O 0.77814(17) 0.7029(6) 0.1156(4) 0.0271(12) Uani 1 1 d . . . O1 O 0.92668(16) 0.4116(6) -0.1007(4) 0.0237(11) Uani 1 1 d . . . O3 O 0.83134(19) 0.8558(6) 0.0639(4) 0.0294(12) Uani 1 1 d . . . O4 O 0.76707(17) 0.2884(6) 0.1077(4) 0.0287(12) Uani 1 1 d . . . H4 H 0.7855 0.2175 0.1070 0.043 Uiso 1 1 calc R . . O8 O 0.81608(19) 0.0661(6) 0.2061(4) 0.0296(12) Uani 1 1 d . . . H8 H 0.7937 0.1126 0.1806 0.044 Uiso 1 1 calc R . . O7 O 0.88171(17) 0.1814(6) 0.5392(4) 0.0273(11) Uani 1 1 d . . . O9 O 0.73811(17) -0.0890(6) 0.3826(4) 0.0262(12) Uani 1 1 d . . . C3 C 0.8237(3) 0.6177(9) -0.0211(5) 0.0245(15) Uani 1 1 d . . . H3 H 0.8053 0.6394 -0.0837 0.029 Uiso 1 1 calc R . . C18 C 0.8728(2) -0.1945(8) 0.4268(5) 0.0229(15) Uani 1 1 d . . . C6 C 0.8962(2) 0.4579(8) 0.0853(5) 0.0223(15) Uani 1 1 d . . . C1 C 0.8652(2) 0.3834(9) 0.0055(5) 0.0224(15) Uani 1 1 d . . . C12 C 0.8119(3) 0.7336(9) 0.0553(6) 0.0257(16) Uani 1 1 d . . . C14 C 0.8302(2) 0.0436(8) 0.3833(5) 0.0206(15) Uani 1 1 d . . . H14 H 0.8340 0.1540 0.3763 0.025 Uiso 1 1 calc R . . C16 C 0.8445(3) -0.0590(8) 0.5526(5) 0.0232(15) Uani 1 1 d . . . C10 C 0.7916(3) 0.4303(9) 0.1041(6) 0.0256(16) Uani 1 1 d . . . H10 H 0.8140 0.4393 0.1620 0.031 Uiso 1 1 calc R . . C13 C 0.8784(3) -0.0279(9) 0.4097(5) 0.0249(16) Uani 1 1 d . . . C4 C 0.8759(3) 0.6199(8) -0.0415(5) 0.0217(15) Uani 1 1 d . . . C11 C 0.7559(3) 0.5537(9) 0.1064(6) 0.0274(16) Uani 1 1 d . . . H11A H 0.7356 0.5502 0.0456 0.033 Uiso 1 1 calc R . . H11B H 0.7372 0.5374 0.1623 0.033 Uiso 1 1 calc R . . O10 O 0.75053(19) -0.1686(6) 0.5363(4) 0.0325(13) Uani 1 1 d . . . C19 C 0.8879(2) 0.0274(8) 0.5198(6) 0.0237(15) Uani 1 1 d . . . C23 C 0.7520(3) 0.0098(9) 0.3041(5) 0.0268(16) Uani 1 1 d . . . H23A H 0.7468 0.1154 0.3215 0.032 Uiso 1 1 calc R . . H23B H 0.7338 -0.0125 0.2423 0.032 Uiso 1 1 calc R . . C22 C 0.8028(3) -0.0160(9) 0.2908(5) 0.0253(16) Uani 1 1 d . . . H22 H 0.8088 -0.1250 0.2826 0.030 Uiso 1 1 calc R . . C25 C 1.0000 0.7127(15) 0.5000 0.038(3) Uani 1 2 d S . . C5 C 0.9037(2) 0.6007(9) 0.0563(5) 0.0244(16) Uani 1 1 d . . . C9 C 0.9499(3) 0.4809(10) -0.1806(6) 0.035(2) Uani 1 1 d . . . H9A H 0.9804 0.4389 -0.1818 0.052 Uiso 1 1 calc R . . H9B H 0.9520 0.5889 -0.1699 0.052 Uiso 1 1 calc R . . H9C H 0.9328 0.4609 -0.2431 0.052 Uiso 1 1 calc R . . C17 C 0.8542(2) -0.2167(8) 0.5123(5) 0.0204(14) Uani 1 1 d . . . C7 C 0.8819(2) 0.4599(8) -0.0887(5) 0.0211(14) Uani 1 1 d . . . C8 C 0.8511(3) 0.3067(9) -0.2250(6) 0.0309(18) Uani 1 1 d . . . H8A H 0.8302 0.3127 -0.2838 0.046 Uiso 1 1 calc R . . H8B H 0.8404 0.2305 -0.1809 0.046 Uiso 1 1 calc R . . H8C H 0.8814 0.2801 -0.2434 0.046 Uiso 1 1 calc R . . C21 C 0.9461(3) -0.0004(12) 0.6566(6) 0.042(2) Uani 1 1 d . . . H21A H 0.9767 -0.0409 0.6703 0.064 Uiso 1 1 calc R . . H21B H 0.9252 -0.0510 0.6976 0.064 Uiso 1 1 calc R . . H21C H 0.9463 0.1068 0.6708 0.064 Uiso 1 1 calc R . . C15 C 0.8055(2) 0.0117(9) 0.4816(5) 0.0216(15) Uani 1 1 d . . . H15 H 0.7967 0.1097 0.5096 0.026 Uiso 1 1 calc R . . C20 C 0.9149(3) 0.2850(9) 0.5025(7) 0.038(2) Uani 1 1 d . . . H20A H 0.9072 0.3874 0.5201 0.057 Uiso 1 1 calc R . . H20B H 0.9144 0.2765 0.4312 0.057 Uiso 1 1 calc R . . H20C H 0.9452 0.2604 0.5316 0.057 Uiso 1 1 calc R . . C24 C 0.7628(2) -0.0895(8) 0.4712(6) 0.0249(16) Uani 1 1 d . . . C2 C 0.8161(2) 0.4462(9) 0.0074(5) 0.0239(15) Uani 1 1 d . . . H2 H 0.7968 0.3980 -0.0467 0.029 Uiso 1 1 calc R . . C26 C 1.0000 0.1741(15) 1.0000 0.041(3) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl5 0.0267(9) 0.0321(10) 0.0333(10) 0.0048(8) 0.0100(8) 0.0006(8) Cl1 0.0259(9) 0.0201(8) 0.0296(9) 0.0003(7) 0.0046(7) 0.0008(7) Cl8 0.0365(10) 0.0266(10) 0.0358(10) -0.0049(8) 0.0098(8) 0.0054(8) Cl2 0.0357(10) 0.0244(9) 0.0305(9) 0.0054(8) 0.0071(8) -0.0016(8) Cl6 0.0346(10) 0.0388(11) 0.0214(9) 0.0004(8) 0.0039(7) 0.0033(9) Cl4 0.0289(9) 0.0307(10) 0.0237(9) 0.0040(8) -0.0013(7) 0.0047(8) Cl7 0.0382(11) 0.0239(9) 0.0447(12) 0.0079(9) 0.0134(9) 0.0035(8) Cl3 0.0304(10) 0.0288(10) 0.0343(10) -0.0033(8) -0.0028(8) -0.0081(8) Cl10 0.0575(15) 0.0402(12) 0.0409(12) -0.0097(10) -0.0091(11) 0.0092(11) Cl9 0.080(2) 0.078(2) 0.0440(14) 0.0077(13) 0.0118(14) -0.0457(17) O6 0.018(2) 0.034(3) 0.033(3) -0.001(2) -0.007(2) 0.005(2) O2 0.019(2) 0.028(3) 0.020(2) 0.002(2) -0.0023(19) 0.004(2) O5 0.026(3) 0.026(3) 0.032(3) 0.002(2) 0.016(2) 0.003(2) O1 0.020(2) 0.029(3) 0.023(3) 0.001(2) 0.007(2) 0.000(2) O3 0.036(3) 0.018(3) 0.036(3) -0.007(2) 0.012(3) -0.004(2) O4 0.026(3) 0.024(3) 0.036(3) 0.002(2) 0.004(2) -0.001(2) O8 0.034(3) 0.023(3) 0.032(3) 0.006(2) 0.002(2) 0.005(2) O7 0.025(3) 0.028(3) 0.028(3) -0.004(2) 0.001(2) -0.004(2) O9 0.023(3) 0.030(3) 0.025(3) 0.005(2) 0.000(2) -0.006(2) C3 0.029(4) 0.025(4) 0.019(3) 0.002(3) -0.002(3) -0.007(3) C18 0.019(3) 0.020(4) 0.031(4) 0.006(3) 0.004(3) 0.002(3) C6 0.021(3) 0.015(3) 0.030(4) 0.001(3) 0.000(3) -0.001(3) C1 0.025(4) 0.023(4) 0.019(3) 0.005(3) -0.003(3) -0.002(3) C12 0.024(4) 0.020(4) 0.032(4) 0.001(3) -0.003(3) 0.009(3) C14 0.007(3) 0.021(4) 0.035(4) 0.004(3) 0.008(3) -0.003(3) C16 0.030(4) 0.012(3) 0.027(4) -0.002(3) -0.001(3) -0.003(3) C10 0.026(4) 0.022(4) 0.030(4) 0.001(3) 0.009(3) -0.010(3) C13 0.023(4) 0.033(4) 0.019(3) 0.003(3) 0.005(3) -0.002(3) C4 0.029(4) 0.016(3) 0.018(3) 0.000(3) -0.005(3) -0.006(3) C11 0.025(4) 0.031(4) 0.026(4) -0.002(3) 0.002(3) 0.000(3) O10 0.028(3) 0.031(3) 0.039(3) 0.008(2) 0.005(3) -0.005(2) C19 0.018(3) 0.019(4) 0.035(4) 0.000(3) 0.004(3) -0.001(3) C23 0.028(4) 0.029(4) 0.022(4) 0.000(3) -0.004(3) 0.002(3) C22 0.035(4) 0.026(4) 0.015(3) 0.003(3) 0.006(3) 0.010(3) C25 0.042(7) 0.042(8) 0.032(6) 0.000 0.012(5) 0.000 C5 0.016(3) 0.030(4) 0.027(4) -0.003(3) 0.001(3) 0.005(3) C9 0.032(4) 0.044(5) 0.030(4) 0.008(4) 0.015(3) 0.001(4) C17 0.023(3) 0.016(3) 0.021(3) -0.005(3) -0.002(3) -0.004(3) C7 0.022(3) 0.007(3) 0.033(4) 0.000(3) -0.001(3) 0.002(3) C8 0.043(5) 0.021(4) 0.027(4) -0.007(3) -0.003(3) 0.003(3) C21 0.033(5) 0.052(6) 0.040(5) -0.010(4) -0.012(4) 0.002(4) C15 0.023(3) 0.023(4) 0.019(3) -0.002(3) -0.002(3) 0.000(3) C20 0.026(4) 0.018(4) 0.072(6) -0.010(4) 0.012(4) -0.001(3) C24 0.022(4) 0.021(4) 0.032(4) -0.005(3) 0.001(3) 0.006(3) C2 0.019(3) 0.029(4) 0.023(4) 0.000(3) -0.005(3) 0.005(3) C26 0.058(8) 0.035(7) 0.029(6) 0.000 -0.009(6) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl5 C13 1.767(7) . ? Cl1 C1 1.789(8) . ? Cl8 C18 1.722(8) . ? Cl2 C4 1.779(7) . ? Cl6 C16 1.762(7) . ? Cl4 C6 1.714(7) . ? Cl7 C17 1.695(8) . ? Cl3 C5 1.706(8) . ? Cl10 C26 1.766(8) . ? Cl9 C25 1.756(8) . ? O6 C19 1.383(8) . ? O6 C21 1.443(9) . ? O2 C7 1.394(8) . ? O2 C8 1.419(9) . ? O5 C12 1.344(9) . ? O5 C11 1.461(9) . ? O1 C7 1.386(8) . ? O1 C9 1.444(8) . ? O3 C12 1.213(9) . ? O4 C10 1.437(9) . ? O8 C22 1.425(8) . ? O7 C19 1.391(9) . ? O7 C20 1.438(9) . ? O9 C24 1.343(9) . ? O9 C23 1.446(9) . ? C3 C12 1.504(10) . ? C3 C4 1.561(10) . ? C3 C2 1.573(11) . ? C18 C17 1.322(10) . ? C18 C13 1.490(10) . ? C6 C5 1.336(11) . ? C6 C1 1.496(10) . ? C1 C2 1.530(10) . ? C1 C7 1.543(10) . ? C14 C22 1.518(10) . ? C14 C13 1.549(9) . ? C14 C15 1.575(9) . ? C16 C17 1.520(10) . ? C16 C15 1.554(10) . ? C16 C19 1.560(10) . ? C10 C11 1.501(11) . ? C10 C2 1.534(10) . ? C13 C19 1.562(10) . ? C4 C5 1.499(10) . ? C4 C7 1.557(10) . ? O10 C24 1.192(9) . ? C23 C22 1.515(10) . ? C25 Cl9 1.756(8) 2_756 ? C15 C24 1.522(10) . ? C26 Cl10 1.766(8) 2_757 ? 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 C19 O6 C21 117.3(6) . . ? C7 O2 C8 116.4(6) . . ? C12 O5 C11 117.8(6) . . ? C7 O1 C9 116.8(6) . . ? C19 O7 C20 116.8(6) . . ? C24 O9 C23 119.4(6) . . ? C12 C3 C4 112.7(6) . . ? C12 C3 C2 115.9(6) . . ? C4 C3 C2 102.1(6) . . ? C17 C18 C13 109.5(6) . . ? C17 C18 Cl8 126.2(6) . . ? C13 C18 Cl8 124.2(5) . . ? C5 C6 C1 107.6(6) . . ? C5 C6 Cl4 127.0(6) . . ? C1 C6 Cl4 125.3(5) . . ? C6 C1 C2 109.9(6) . . ? C6 C1 C7 101.0(6) . . ? C2 C1 C7 102.0(6) . . ? C6 C1 Cl1 113.4(5) . . ? C2 C1 Cl1 113.8(5) . . ? C7 C1 Cl1 115.5(5) . . ? O3 C12 O5 118.4(7) . . ? O3 C12 C3 122.3(7) . . ? O5 C12 C3 119.3(7) . . ? C22 C14 C13 117.1(6) . . ? C22 C14 C15 112.5(5) . . ? C13 C14 C15 101.3(5) . . ? C17 C16 C15 106.9(6) . . ? C17 C16 C19 99.6(6) . . ? C15 C16 C19 101.4(6) . . ? C17 C16 Cl6 115.6(5) . . ? C15 C16 Cl6 114.7(5) . . ? C19 C16 Cl6 116.6(5) . . ? O4 C10 C11 106.3(6) . . ? O4 C10 C2 111.7(6) . . ? C11 C10 C2 108.4(6) . . ? C18 C13 C14 109.1(6) . . ? C18 C13 C19 99.9(6) . . ? C14 C13 C19 100.6(6) . . ? C18 C13 Cl5 114.8(5) . . ? C14 C13 Cl5 113.6(5) . . ? C19 C13 Cl5 117.2(5) . . ? C5 C4 C7 100.8(6) . . ? C5 C4 C3 108.0(6) . . ? C7 C4 C3 101.6(6) . . ? C5 C4 Cl2 115.9(5) . . ? C7 C4 Cl2 116.1(5) . . ? C3 C4 Cl2 112.9(5) . . ? O5 C11 C10 110.3(6) . . ? O6 C19 O7 112.8(6) . . ? O6 C19 C16 119.0(6) . . ? O7 C19 C16 107.5(6) . . ? O6 C19 C13 107.1(6) . . ? O7 C19 C13 117.6(6) . . ? C16 C19 C13 91.6(5) . . ? O9 C23 C22 108.8(6) . . ? O8 C22 C23 110.0(6) . . ? O8 C22 C14 108.9(6) . . ? C23 C22 C14 107.8(6) . . ? Cl9 C25 Cl9 111.3(7) . 2_756 ? C6 C5 C4 105.8(6) . . ? C6 C5 Cl3 129.1(6) . . ? C4 C5 Cl3 125.0(6) . . ? C18 C17 C16 105.9(6) . . ? C18 C17 Cl7 128.4(6) . . ? C16 C17 Cl7 125.7(5) . . ? O1 C7 O2 113.2(6) . . ? O1 C7 C1 108.5(6) . . ? O2 C7 C1 117.2(6) . . ? O1 C7 C4 117.3(6) . . ? O2 C7 C4 108.6(6) . . ? C1 C7 C4 90.3(5) . . ? C24 C15 C16 111.9(6) . . ? C24 C15 C14 116.4(6) . . ? C16 C15 C14 103.3(6) . . ? O10 C24 O9 119.0(7) . . ? O10 C24 C15 124.0(7) . . ? O9 C24 C15 117.1(6) . . ? C1 C2 C10 118.2(6) . . ? C1 C2 C3 101.2(6) . . ? C10 C2 C3 112.1(6) . . ? Cl10 C26 Cl10 112.1(7) 2_757 . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.714 _refine_diff_density_min -0.749 _refine_diff_density_rms 0.159