# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_wagner4 _database_code_depnum_ccdc_archive 'CCDC 715259' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Cl2 O2' _chemical_formula_sum 'C12 H10 Cl2 O2' _chemical_formula_weight 257.10 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.2064(2) _cell_length_b 7.7304(4) _cell_length_c 21.6681(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.591(3) _cell_angle_gamma 90.00 _cell_volume 1190.22(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5052 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 27.485 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.526 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8304 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0489 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2719 _reflns_number_gt 1823 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+0.0432P] 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 2719 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _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 -0.5719(3) -0.2999(3) -0.32782(10) 0.0356(5) Uani 1 1 d . . . C2 C -0.5223(3) -0.3602(3) -0.26707(10) 0.0368(5) Uani 1 1 d . . . H2 H -0.6114 -0.4200 -0.2472 0.044 Uiso 1 1 calc R . . C3 C -0.3423(3) -0.3322(3) -0.23584(10) 0.0339(5) Uani 1 1 d . . . H3 H -0.3080 -0.3730 -0.1941 0.041 Uiso 1 1 calc R . . C4 C -0.2088(3) -0.2450(3) -0.26426(9) 0.0295(5) Uani 1 1 d . . . C5 C -0.2635(3) -0.1892(3) -0.32583(9) 0.0325(5) Uani 1 1 d . . . H5 H -0.1744 -0.1317 -0.3463 0.039 Uiso 1 1 calc R . . C6 C -0.4443(3) -0.2153(3) -0.35791(9) 0.0348(5) Uani 1 1 d . . . H6 H -0.4795 -0.1757 -0.3997 0.042 Uiso 1 1 calc R . . C7 C -0.0206(3) -0.2013(3) -0.23114(9) 0.0342(5) Uani 1 1 d . . . H7 H 0.0556 -0.1329 -0.2534 0.041 Uiso 1 1 calc R . . C8 C 0.0556(3) -0.2474(3) -0.17297(9) 0.0341(5) Uani 1 1 d . . . H8 H -0.0118 -0.3244 -0.1507 0.041 Uiso 1 1 calc R . . C9 C 0.2365(3) -0.1845(3) -0.14282(10) 0.0360(5) Uani 1 1 d . . . H9 H 0.2985 -0.1038 -0.1654 0.043 Uiso 1 1 calc R . . C10 C 0.3242(3) -0.2293(3) -0.08635(10) 0.0371(5) Uani 1 1 d . . . C11 C 0.6517(3) -0.2348(3) -0.05077(10) 0.0354(5) Uani 1 1 d . . . C12 C 0.7983(3) -0.1433(3) -0.00585(11) 0.0466(6) Uani 1 1 d . . . H12A H 0.7662 -0.1497 0.0363 0.070 Uiso 1 1 calc R . . H12B H 0.8043 -0.0218 -0.0183 0.070 Uiso 1 1 calc R . . H12C H 0.9208 -0.1982 -0.0060 0.070 Uiso 1 1 calc R . . Cl1 Cl -0.80163(8) -0.33141(11) -0.36670(3) 0.0566(3) Uani 1 1 d . . . Cl2 Cl 0.24144(8) -0.38103(9) -0.03875(3) 0.0454(2) Uani 1 1 d . . . O1 O 0.4831(2) -0.1457(2) -0.05610(7) 0.0433(4) Uani 1 1 d . . . O2 O 0.6672(2) -0.3646(2) -0.07863(7) 0.0433(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0290(10) 0.0396(14) 0.0366(12) -0.0071(10) 0.0011(9) -0.0009(9) C2 0.0377(11) 0.0366(15) 0.0369(13) -0.0023(10) 0.0084(10) -0.0065(10) C3 0.0390(11) 0.0319(13) 0.0303(11) 0.0007(9) 0.0038(9) -0.0014(9) C4 0.0328(10) 0.0248(12) 0.0293(11) -0.0008(9) 0.0006(8) 0.0001(9) C5 0.0344(11) 0.0310(12) 0.0319(11) 0.0022(10) 0.0050(9) 0.0002(9) C6 0.0375(11) 0.0354(14) 0.0294(11) 0.0013(10) -0.0005(9) 0.0054(10) C7 0.0323(11) 0.0320(13) 0.0376(12) -0.0001(10) 0.0034(9) -0.0018(9) C8 0.0349(11) 0.0311(13) 0.0352(12) -0.0030(9) 0.0024(9) 0.0017(9) C9 0.0358(11) 0.0307(13) 0.0388(12) -0.0014(10) -0.0014(9) 0.0012(10) C10 0.0347(11) 0.0328(13) 0.0415(13) -0.0063(10) -0.0009(9) 0.0019(10) C11 0.0323(11) 0.0395(15) 0.0335(12) 0.0035(11) 0.0029(9) 0.0001(10) C12 0.0369(12) 0.0494(17) 0.0492(15) -0.0041(12) -0.0057(10) -0.0037(10) Cl1 0.0318(3) 0.0860(6) 0.0489(4) -0.0062(3) -0.0026(3) -0.0069(3) Cl2 0.0449(3) 0.0533(4) 0.0362(3) 0.0035(3) 0.0014(2) 0.0038(3) O1 0.0363(8) 0.0380(10) 0.0496(10) -0.0119(7) -0.0101(7) 0.0026(7) O2 0.0436(9) 0.0432(11) 0.0424(9) -0.0074(8) 0.0053(7) 0.0022(7) _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 1.378(3) . ? C1 C2 1.386(3) . ? C1 Cl1 1.745(2) . ? C2 C3 1.377(3) . ? C2 H2 0.9500 . ? C3 C4 1.399(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C4 C7 1.464(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.337(3) . ? C7 H7 0.9500 . ? C8 C9 1.442(3) . ? C8 H8 0.9500 . ? C9 C10 1.326(3) . ? C9 H9 0.9500 . ? C10 O1 1.382(3) . ? C10 Cl2 1.732(2) . ? C11 O2 1.186(3) . ? C11 O1 1.384(3) . ? C11 C12 1.490(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 121.49(19) . . ? C6 C1 Cl1 119.47(16) . . ? C2 C1 Cl1 119.04(16) . . ? C3 C2 C1 119.14(19) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 121.33(19) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C5 C4 C3 117.69(19) . . ? C5 C4 C7 119.26(18) . . ? C3 C4 C7 122.94(18) . . ? C6 C5 C4 121.81(19) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? C1 C6 C5 118.53(19) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C8 C7 C4 127.0(2) . . ? C8 C7 H7 116.5 . . ? C4 C7 H7 116.5 . . ? C7 C8 C9 122.4(2) . . ? C7 C8 H8 118.8 . . ? C9 C8 H8 118.8 . . ? C10 C9 C8 125.9(2) . . ? C10 C9 H9 117.1 . . ? C8 C9 H9 117.1 . . ? C9 C10 O1 123.1(2) . . ? C9 C10 Cl2 124.61(18) . . ? O1 C10 Cl2 112.00(15) . . ? O2 C11 O1 122.3(2) . . ? O2 C11 C12 128.1(2) . . ? O1 C11 C12 109.6(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 O1 C11 116.97(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.0(3) . . . . ? Cl1 C1 C2 C3 -178.62(17) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C2 C3 C4 C7 175.3(2) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C7 C4 C5 C6 -175.1(2) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? Cl1 C1 C6 C5 178.96(17) . . . . ? C4 C5 C6 C1 -0.5(3) . . . . ? C5 C4 C7 C8 -178.3(2) . . . . ? C3 C4 C7 C8 5.5(4) . . . . ? C4 C7 C8 C9 -174.4(2) . . . . ? C7 C8 C9 C10 -177.3(2) . . . . ? C8 C9 C10 O1 -169.9(2) . . . . ? C8 C9 C10 Cl2 3.0(4) . . . . ? C9 C10 O1 C11 -108.4(2) . . . . ? Cl2 C10 O1 C11 78.0(2) . . . . ? O2 C11 O1 C10 11.4(3) . . . . ? C12 C11 O1 C10 -167.95(18) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.378 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.093 data_wagner2 _database_code_depnum_ccdc_archive 'CCDC 715260' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Cl O3' _chemical_formula_sum 'C11 H11 Cl O3' _chemical_formula_weight 226.65 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5568(9) _cell_length_b 5.6463(8) _cell_length_c 12.8318(11) _cell_angle_alpha 90.00 _cell_angle_beta 92.578(7) _cell_angle_gamma 90.00 _cell_volume 546.95(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3875 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.332 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3273 _diffrn_reflns_av_R_equivalents 0.0460 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 27.39 _reflns_number_total 2100 _reflns_number_gt 1545 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+0.1506P] 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(14) _refine_ls_number_reflns 2100 _refine_ls_number_parameters 138 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_ref 0.1674 _refine_ls_wR_factor_gt 0.1400 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.110 _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 0.5538(9) 0.1357(17) 0.2897(5) 0.085(3) Uani 1 1 d . . . H1 H 0.4954 0.0696 0.3470 0.102 Uiso 1 1 calc R . . C2 C 0.6453(9) 0.3219(16) 0.2951(5) 0.084(3) Uani 1 1 d . . . H2 H 0.6696 0.4130 0.3563 0.101 Uiso 1 1 calc R . . C3 C 0.7092(6) 0.3759(11) 0.1896(3) 0.0467(11) Uani 1 1 d . . . H3 H 0.7770 0.5070 0.1678 0.056 Uiso 1 1 calc R . . C4 C 0.6466(5) 0.1925(8) 0.1336(3) 0.0351(10) Uani 1 1 d . . . C5 C 0.6678(5) 0.1255(8) 0.0253(3) 0.0320(9) Uani 1 1 d . . . H5 H 0.6159 -0.0220 0.0057 0.038 Uiso 1 1 calc R . . C6 C 0.7478(5) 0.2374(8) -0.0503(3) 0.0311(10) Uani 1 1 d . . . C7 C 0.8291(6) 0.4816(9) -0.0350(4) 0.0435(12) Uani 1 1 d . . . H7A H 0.7848 0.5538 0.0281 0.065 Uiso 1 1 calc R . . H7B H 0.7966 0.5811 -0.0955 0.065 Uiso 1 1 calc R . . H7C H 0.9583 0.4674 -0.0280 0.065 Uiso 1 1 calc R . . C8 C 0.7577(5) 0.1141(8) -0.1496(3) 0.0326(9) Uani 1 1 d . . . H8 H 0.6856 -0.0236 -0.1551 0.039 Uiso 1 1 calc R . . C9 C 0.8479(6) 0.1575(8) -0.2336(3) 0.0378(11) Uani 1 1 d . . . C10 C 0.7617(6) 0.0301(10) -0.4044(3) 0.0443(12) Uani 1 1 d . . . C11 C 0.7855(8) -0.1669(10) -0.4791(4) 0.0579(15) Uani 1 1 d . . . H11A H 0.6783 -0.1835 -0.5244 0.087 Uiso 1 1 calc R . . H11B H 0.8072 -0.3146 -0.4404 0.087 Uiso 1 1 calc R . . H11C H 0.8868 -0.1327 -0.5217 0.087 Uiso 1 1 calc R . . O1 O 0.5483(5) 0.0398(9) 0.1915(3) 0.0704(11) Uani 1 1 d . . . O2 O 0.8519(4) -0.0138(5) -0.3125(2) 0.0413(8) Uani 1 1 d . . . O3 O 0.6764(5) 0.2071(7) -0.4197(3) 0.0571(10) Uani 1 1 d . . . Cl1 Cl 0.98776(16) 0.3910(3) -0.25643(9) 0.0556(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.073(4) 0.138(8) 0.045(3) 0.021(4) 0.008(3) 0.037(5) C2 0.077(4) 0.120(7) 0.053(3) -0.052(4) -0.025(3) 0.032(4) C3 0.039(2) 0.050(3) 0.051(2) -0.019(3) 0.0012(18) -0.007(3) C4 0.030(2) 0.038(3) 0.037(2) 0.003(2) -0.0026(17) -0.0034(19) C5 0.031(2) 0.025(2) 0.039(2) -0.002(2) -0.0053(17) -0.0016(17) C6 0.027(2) 0.029(2) 0.036(2) 0.001(2) -0.0054(17) 0.0040(19) C7 0.054(3) 0.032(3) 0.044(3) -0.003(2) 0.002(2) -0.011(2) C8 0.036(2) 0.028(2) 0.033(2) 0.0002(19) -0.0063(17) 0.0021(19) C9 0.043(2) 0.033(3) 0.038(2) 0.002(2) -0.0029(19) 0.004(2) C10 0.055(3) 0.046(3) 0.033(2) 0.000(2) 0.011(2) -0.004(3) C11 0.088(4) 0.045(4) 0.041(3) -0.005(3) 0.004(3) 0.004(3) O1 0.066(2) 0.073(3) 0.072(3) 0.018(2) 0.0087(19) 0.000(2) O2 0.0496(18) 0.0357(19) 0.0382(15) -0.0040(15) -0.0015(13) 0.0077(15) O3 0.079(3) 0.048(2) 0.0437(18) -0.0006(17) -0.0064(17) 0.014(2) Cl1 0.0592(7) 0.0551(8) 0.0535(7) -0.0026(7) 0.0133(5) -0.0184(7) _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 1.259(11) . ? C1 O1 1.371(8) . ? C1 H1 0.9500 . ? C2 C3 1.489(9) . ? C2 H2 0.9500 . ? C3 C4 1.335(7) . ? C3 H3 0.9500 . ? C4 O1 1.377(6) . ? C4 C5 1.456(6) . ? C5 C6 1.326(6) . ? C5 H5 0.9500 . ? C6 C8 1.457(6) . ? C6 C7 1.518(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.324(6) . ? C8 H8 0.9500 . ? C9 O2 1.401(5) . ? C9 Cl1 1.723(5) . ? C10 O3 1.201(6) . ? C10 O2 1.359(6) . ? C10 C11 1.485(7) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 O1 111.9(6) . . ? C2 C1 H1 124.0 . . ? O1 C1 H1 124.0 . . ? C1 C2 C3 108.8(5) . . ? C1 C2 H2 125.6 . . ? C3 C2 H2 125.6 . . ? C4 C3 C2 102.1(5) . . ? C4 C3 H3 129.0 . . ? C2 C3 H3 129.0 . . ? C3 C4 O1 112.5(4) . . ? C3 C4 C5 131.6(4) . . ? O1 C4 C5 115.9(4) . . ? C6 C5 C4 130.4(4) . . ? C6 C5 H5 114.8 . . ? C4 C5 H5 114.8 . . ? C5 C6 C8 117.1(4) . . ? C5 C6 C7 122.2(4) . . ? C8 C6 C7 120.6(4) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C6 132.3(4) . . ? C9 C8 H8 113.9 . . ? C6 C8 H8 113.9 . . ? C8 C9 O2 119.3(4) . . ? C8 C9 Cl1 128.5(3) . . ? O2 C9 Cl1 111.9(3) . . ? O3 C10 O2 122.6(4) . . ? O3 C10 C11 126.7(4) . . ? O2 C10 C11 110.6(4) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 O1 C4 104.7(5) . . ? C10 O2 C9 118.3(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 2.3(8) . . . . ? C1 C2 C3 C4 -2.7(7) . . . . ? C2 C3 C4 O1 2.1(5) . . . . ? C2 C3 C4 C5 -176.3(5) . . . . ? C3 C4 C5 C6 -4.5(8) . . . . ? O1 C4 C5 C6 177.2(4) . . . . ? C4 C5 C6 C8 175.5(4) . . . . ? C4 C5 C6 C7 -3.5(7) . . . . ? C5 C6 C8 C9 -168.6(4) . . . . ? C7 C6 C8 C9 10.5(7) . . . . ? C6 C8 C9 O2 170.2(4) . . . . ? C6 C8 C9 Cl1 -1.8(7) . . . . ? C2 C1 O1 C4 -1.0(7) . . . . ? C3 C4 O1 C1 -0.9(6) . . . . ? C5 C4 O1 C1 177.7(4) . . . . ? O3 C10 O2 C9 -1.5(7) . . . . ? C11 C10 O2 C9 178.3(4) . . . . ? C8 C9 O2 C10 109.2(5) . . . . ? Cl1 C9 O2 C10 -77.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.285 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.068