# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 # Attachment '4iR.cif' data_global3 _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef '4iR.cif' #============================================================================ # 1. SUBMISSION DETAILS _publ_contact_author ; Dr. J. F. Malone School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; _publ_contact_author_phone '0044 2890 274421' _publ_contact_author_fax '0044 2890 974687' _publ_contact_author_email dr.boyd@qub.ac.uk _publ_requested_coeditor_name ? #============================================================================ # 2. TITLE AND AUTHOR LIST _publ_section_title ;Structure, stereochemistry and synthesis of enantiopure cyclohexenone cis-diol bacterial metabolites derived from phenols ; loop_ _publ_author_name _publ_author_address D.R.Boyd ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; N.D.Sharma ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; J.F.Malone ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; P.B.A.McIntyre ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; P.J.Stevenson ; School of Chemistry and Chemical Engineering The Queen's University of Belfast Belfast UK BT9 5AG ; ; C.McRoberts ; ; Agri-food and Biosciences Institute for Northern Ireland Belfast UK BT9 5AG ; J.Gawronski ; Department of Chemistry A Mickiewicz University Poznan 6078 Poland ; M.Kwit ; Department of Chemistry A Mickiewicz University Poznan 6078 Poland ; C.C.R.Allen ; School of Biological Sciences The Queen's University of Belfast Belfast UK BT9 5AG ; _publ_contact_author_name 'Dr. J. F. Malone' #============================================================================ data_4gR _database_code_depnum_ccdc_archive 'CCDC 852568' #TrackingRef '4gR.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 F O3' _chemical_formula_sum 'C7 H9 F O3' _chemical_formula_weight 160.14 _chemical_absolute_configuration syn 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 4.641(2) _cell_length_b 10.535(3) _cell_length_c 15.936(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 779.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3415 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 27.95 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 'Bruker SMART CCD area detector' _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 3415 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 27.95 _reflns_number_total 1482 _reflns_number_gt 1205 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0603P)^2^+0.0327P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.1(14) _refine_ls_number_reflns 1482 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1151 _refine_ls_wR_factor_gt 0.1107 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.003 _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 0.7850(5) 0.98591(18) 0.24359(14) 0.0497(5) Uani 1 1 d . . . O1 O 0.8967(5) 1.01891(15) 0.30879(11) 0.0752(5) Uani 1 1 d . . . C2 C 0.8144(5) 1.05404(18) 0.16638(15) 0.0571(6) Uani 1 1 d . . . H2 H 0.8934 1.1351 0.1680 0.068 Uiso 1 1 calc R . . C3 C 0.7344(5) 1.0072(2) 0.09237(14) 0.0564(6) Uani 1 1 d . . . C4 C 0.5930(5) 0.87903(18) 0.08671(14) 0.0498(5) Uani 1 1 d . . . H4 H 0.3838 0.8916 0.0853 0.060 Uiso 1 1 calc R . . O4 O 0.6767(4) 0.81933(16) 0.01114(10) 0.0630(5) Uani 1 1 d . . . H4' H 0.5387 0.7812 -0.0088 0.076 Uiso 1 1 calc R . . C5 C 0.6639(4) 0.79634(18) 0.16098(13) 0.0461(5) Uani 1 1 d . . . H5 H 0.5487 0.7184 0.1591 0.055 Uiso 1 1 calc R . . O5 O 0.9614(3) 0.76593(12) 0.15841(10) 0.0510(4) Uani 1 1 d . . . H5' H 0.9830 0.6902 0.1685 0.061 Uiso 1 1 calc R . . C6 C 0.6013(5) 0.86774(18) 0.24001(14) 0.0525(6) Uani 1 1 d . . . H6 H 0.3980 0.8930 0.2397 0.063 Uiso 1 1 calc R . . F6 F 0.6508(4) 0.79296(14) 0.30924(9) 0.0785(5) Uani 1 1 d . . . C7 C 0.7774(11) 1.0783(3) 0.0123(2) 0.1059(14) Uani 1 1 d . . . H7A H 0.8529 1.1612 0.0243 0.159 Uiso 1 1 calc R . . H7B H 0.5963 1.0865 -0.0163 0.159 Uiso 1 1 calc R . . H7C H 0.9108 1.0330 -0.0227 0.159 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0537(12) 0.0409(10) 0.0545(12) -0.0176(10) 0.0015(10) 0.0010(10) O1 0.1015(13) 0.0615(9) 0.0625(10) -0.0159(8) -0.0069(10) -0.0196(10) C2 0.0707(14) 0.0317(9) 0.0688(14) -0.0060(9) -0.0064(13) 0.0001(10) C3 0.0636(13) 0.0407(10) 0.0648(13) -0.0002(11) -0.0090(11) 0.0055(10) C4 0.0394(10) 0.0487(10) 0.0612(13) -0.0161(10) -0.0064(10) 0.0048(9) O4 0.0597(10) 0.0671(10) 0.0622(10) -0.0237(8) -0.0103(8) 0.0012(9) C5 0.0343(10) 0.0356(8) 0.0683(14) -0.0078(9) 0.0037(10) -0.0057(7) O5 0.0396(8) 0.0363(6) 0.0771(10) -0.0009(7) 0.0037(7) 0.0038(6) C6 0.0468(12) 0.0520(11) 0.0588(14) -0.0055(10) 0.0076(11) -0.0042(10) F6 0.0949(12) 0.0730(8) 0.0676(9) 0.0054(7) 0.0119(8) -0.0210(8) C7 0.167(4) 0.0688(17) 0.082(2) 0.0165(15) -0.028(2) -0.017(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.212(3) . ? C1 C2 1.431(4) . ? C1 C6 1.510(4) . ? C2 C3 1.331(4) . ? C2 H2 0.9300 . ? C3 C7 1.493(5) . ? C3 C4 1.504(4) . ? C4 O4 1.413(4) . ? C4 C5 1.506(4) . ? C4 H4 0.9800 . ? O4 H4' 0.8200 . ? C5 O5 1.418(4) . ? C5 C6 1.495(4) . ? C5 H5 0.9800 . ? O5 H5' 0.8200 . ? C6 F6 1.375(4) . ? C6 H6 0.9800 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 123.5(2) . . ? O1 C1 C6 120.7(2) . . ? C2 C1 C6 115.8(2) . . ? C3 C2 C1 123.3(3) . . ? C3 C2 H2 118.3 . . ? C1 C2 H2 118.3 . . ? C2 C3 C7 122.3(3) . . ? C2 C3 C4 120.5(2) . . ? C7 C3 C4 117.2(2) . . ? O4 C4 C3 109.3(2) . . ? O4 C4 C5 110.6(2) . . ? C3 C4 C5 112.2(2) . . ? O4 C4 H4 108.2 . . ? C3 C4 H4 108.2 . . ? C5 C4 H4 108.2 . . ? C4 O4 H4' 109.5 . . ? O5 C5 C6 109.10(18) . . ? O5 C5 C4 108.70(18) . . ? C6 C5 C4 109.2(2) . . ? O5 C5 H5 109.9 . . ? C6 C5 H5 109.9 . . ? C4 C5 H5 109.9 . . ? C5 O5 H5' 109.5 . . ? F6 C6 C5 110.8(2) . . ? F6 C6 C1 110.3(2) . . ? C5 C6 C1 109.7(2) . . ? F6 C6 H6 108.7 . . ? C5 C6 H6 108.7 . . ? C1 C6 H6 108.7 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 168.1(2) . . . . ? C6 C1 C2 C3 -12.2(3) . . . . ? C1 C2 C3 C7 -177.6(3) . . . . ? C1 C2 C3 C4 2.8(4) . . . . ? C2 C3 C4 O4 -146.2(2) . . . . ? C7 C3 C4 O4 34.3(3) . . . . ? C2 C3 C4 C5 -23.1(3) . . . . ? C7 C3 C4 C5 157.4(3) . . . . ? O4 C4 C5 O5 55.2(2) . . . . ? C3 C4 C5 O5 -67.1(2) . . . . ? O4 C4 C5 C6 174.13(18) . . . . ? C3 C4 C5 C6 51.8(3) . . . . ? O5 C5 C6 F6 -64.1(2) . . . . ? C4 C5 C6 F6 177.20(18) . . . . ? O5 C5 C6 C1 57.9(2) . . . . ? C4 C5 C6 C1 -60.8(3) . . . . ? O1 C1 C6 F6 -16.7(3) . . . . ? C2 C1 C6 F6 163.65(18) . . . . ? O1 C1 C6 C5 -139.0(2) . . . . ? C2 C1 C6 C5 41.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.155 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.039 #============================================================================ data_4gR-cam _database_code_depnum_ccdc_archive 'CCDC 852569' #TrackingRef '4gRcam.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 F O6' _chemical_formula_sum 'C17 H21 F O6' _chemical_formula_weight 340.34 _chemical_absolute_configuration rm 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2716(12) _cell_length_b 10.4218(18) _cell_length_c 10.0531(18) _cell_angle_alpha 90.00 _cell_angle_beta 106.384(13) _cell_angle_gamma 90.00 _cell_volume 831.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 35 _cell_measurement_theta_min 3.42 _cell_measurement_theta_max 12.52 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.109 _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 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 'Bruker P4 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2103 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1723 _reflns_number_gt 1619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0561P)^2^+0.0456P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.088(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(9) _refine_ls_number_reflns 1723 _refine_ls_number_parameters 223 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0303 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 1.3297(3) 1.0278(3) 0.4873(2) 0.0412(5) Uani 1 1 d . . . O1 O 1.3606(2) 1.1421(2) 0.4915(2) 0.0623(5) Uani 1 1 d . . . C2 C 1.2098(3) 0.9693(2) 0.5510(2) 0.0374(5) Uani 1 1 d . . . H2 H 1.1603 1.0215 0.6036 0.045 Uiso 1 1 calc R . . C3 C 1.1665(3) 0.8452(2) 0.5388(2) 0.0364(5) Uani 1 1 d . . . C4 C 1.2443(3) 0.7540(2) 0.4563(2) 0.0371(5) Uani 1 1 d . . . H4 H 1.3429 0.7130 0.5196 0.045 Uiso 1 1 calc R . . O4 O 1.1261(2) 0.65785(19) 0.3945(2) 0.0561(5) Uani 1 1 d . . . H4A H 1.1741 0.5998 0.3656 0.084 Uiso 1 1 calc R . . C5 C 1.3013(2) 0.8284(2) 0.3457(2) 0.0358(5) Uani 1 1 d . . . H5 H 1.3554 0.7713 0.2936 0.043 Uiso 1 1 calc R . . O5 O 1.15081(18) 0.88721(17) 0.25503(13) 0.0400(4) Uani 1 1 d . . . C6 C 1.4184(3) 0.9342(3) 0.4146(2) 0.0401(5) Uani 1 1 d . . . H6 H 1.5134 0.8958 0.4845 0.048 Uiso 1 1 calc R . . F6 F 1.4812(2) 0.99963(19) 0.31990(16) 0.0649(5) Uani 1 1 d . . . C7 C 1.0433(4) 0.7903(3) 0.6069(3) 0.0623(8) Uani 1 1 d . . . H7A H 1.0165 0.8535 0.6669 0.093 Uiso 1 1 calc R . . H7B H 1.0918 0.7163 0.6604 0.093 Uiso 1 1 calc R . . H7C H 0.9425 0.7656 0.5374 0.093 Uiso 1 1 calc R . . C8 C 1.0935(2) 0.8481(2) 0.12443(19) 0.0289(4) Uani 1 1 d . . . O8 O 1.1671(2) 0.7806(2) 0.06573(16) 0.0541(5) Uani 1 1 d . . . C9 C 0.9167(2) 0.9017(2) 0.06077(18) 0.0275(4) Uani 1 1 d . . . O9 O 0.90629(17) 0.94058(16) -0.08180(12) 0.0329(4) Uani 1 1 d . . . C10 C 0.8605(3) 1.0184(2) 0.1292(2) 0.0334(5) Uani 1 1 d . . . H10A H 0.9189 1.0957 0.1150 0.040 Uiso 1 1 calc R . . H10B H 0.8782 1.0051 0.2277 0.040 Uiso 1 1 calc R . . C11 C 0.6701(3) 1.0248(2) 0.0505(2) 0.0372(5) Uani 1 1 d . . . H11A H 0.6429 1.1041 -0.0015 0.045 Uiso 1 1 calc R . . H11B H 0.6015 1.0182 0.1142 0.045 Uiso 1 1 calc R . . C12 C 0.6430(2) 0.9072(2) -0.04802(19) 0.0314(5) Uani 1 1 d . . . C13 C 0.7394(3) 0.9458(2) -0.14984(19) 0.0335(5) Uani 1 1 d . . . O13 O 0.6897(2) 0.98064(18) -0.26868(14) 0.0470(5) Uani 1 1 d . . . C14 C 0.7664(2) 0.8059(2) 0.03844(19) 0.0303(5) Uani 1 1 d . . . C15 C 0.7291(3) 0.7647(3) 0.1727(2) 0.0424(6) Uani 1 1 d . . . H15A H 0.8237 0.7182 0.2295 0.064 Uiso 1 1 calc R . . H15B H 0.6311 0.7107 0.1511 0.064 Uiso 1 1 calc R . . H15C H 0.7091 0.8393 0.2218 0.064 Uiso 1 1 calc R . . C16 C 0.7828(3) 0.6862(2) -0.0449(2) 0.0414(5) Uani 1 1 d . . . H16A H 0.8095 0.7113 -0.1282 0.062 Uiso 1 1 calc R . . H16B H 0.6783 0.6398 -0.0686 0.062 Uiso 1 1 calc R . . H16C H 0.8710 0.6324 0.0097 0.062 Uiso 1 1 calc R . . C17 C 0.4605(3) 0.8702(3) -0.1145(3) 0.0475(6) Uani 1 1 d . . . H17A H 0.4001 0.9428 -0.1629 0.071 Uiso 1 1 calc R . . H17B H 0.4102 0.8432 -0.0440 0.071 Uiso 1 1 calc R . . H17C H 0.4558 0.8011 -0.1788 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0333(11) 0.0414(14) 0.0428(11) -0.0022(11) 0.0008(9) -0.0005(11) O1 0.0550(11) 0.0405(10) 0.0906(14) -0.0053(11) 0.0193(10) -0.0100(10) C2 0.0376(11) 0.0423(13) 0.0319(10) -0.0069(10) 0.0091(8) 0.0027(10) C3 0.0340(11) 0.0430(13) 0.0307(10) 0.0020(10) 0.0065(8) 0.0044(11) C4 0.0320(11) 0.0354(12) 0.0407(11) -0.0001(10) 0.0048(9) 0.0037(9) O4 0.0472(9) 0.0399(10) 0.0838(13) -0.0187(10) 0.0229(9) -0.0056(9) C5 0.0262(10) 0.0467(13) 0.0321(10) -0.0038(10) 0.0040(8) 0.0100(10) O5 0.0361(8) 0.0500(10) 0.0282(7) -0.0055(7) 0.0001(6) 0.0148(8) C6 0.0302(10) 0.0511(14) 0.0389(11) 0.0063(11) 0.0095(9) 0.0029(11) F6 0.0622(10) 0.0741(12) 0.0691(9) 0.0120(9) 0.0360(8) -0.0051(9) C7 0.0728(19) 0.0600(18) 0.0664(16) 0.0010(16) 0.0397(14) -0.0073(16) C8 0.0268(9) 0.0311(10) 0.0296(9) -0.0054(9) 0.0092(8) -0.0044(9) O8 0.0379(9) 0.0774(14) 0.0436(8) -0.0220(10) 0.0062(7) 0.0155(9) C9 0.0274(9) 0.0296(10) 0.0250(8) -0.0005(8) 0.0065(7) -0.0020(8) O9 0.0316(7) 0.0399(8) 0.0274(6) 0.0013(6) 0.0088(5) -0.0052(7) C10 0.0331(10) 0.0315(11) 0.0353(9) -0.0032(9) 0.0091(8) 0.0012(9) C11 0.0360(11) 0.0343(12) 0.0424(11) 0.0034(10) 0.0131(9) 0.0072(10) C12 0.0267(10) 0.0350(12) 0.0304(10) 0.0063(9) 0.0046(8) -0.0006(9) C13 0.0338(10) 0.0332(11) 0.0310(10) 0.0022(9) 0.0050(8) -0.0033(10) O13 0.0491(9) 0.0570(12) 0.0296(7) 0.0100(8) 0.0027(6) -0.0058(9) C14 0.0259(9) 0.0307(11) 0.0337(9) 0.0032(9) 0.0075(7) -0.0001(9) C15 0.0369(12) 0.0454(14) 0.0461(12) 0.0163(11) 0.0136(10) -0.0004(11) C16 0.0359(11) 0.0311(11) 0.0529(13) -0.0055(10) 0.0053(10) -0.0053(10) C17 0.0285(11) 0.0545(16) 0.0526(12) 0.0113(12) 0.0002(9) -0.0036(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 C1 O1 1.216(3) . ? C1 C2 1.458(3) . ? C1 C6 1.526(3) . ? C2 C3 1.338(4) . ? C2 H2 0.9300 . ? C3 C7 1.493(3) . ? C3 C4 1.519(3) . ? C4 O4 1.416(3) . ? C4 C5 1.535(3) . ? C4 H4 0.9800 . ? O4 H4A 0.8200 . ? C5 O5 1.455(2) . ? C5 C6 1.501(3) . ? C5 H5 0.9800 . ? O5 C8 1.328(2) . ? C6 F6 1.385(3) . ? C6 H6 0.9800 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 O8 1.189(3) . ? C8 C9 1.528(3) . ? C9 O9 1.468(2) . ? C9 C10 1.532(3) . ? C9 C14 1.560(3) . ? O9 C13 1.358(2) . ? C10 C11 1.551(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.552(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.518(3) . ? C12 C13 1.519(3) . ? C12 C14 1.552(3) . ? C13 O13 1.204(2) . ? C14 C15 1.528(3) . ? C14 C16 1.530(3) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C2 123.8(2) . . ? O1 C1 C6 121.2(2) . . ? C2 C1 C6 114.9(2) . . ? C3 C2 C1 124.2(2) . . ? C3 C2 H2 117.9 . . ? C1 C2 H2 117.9 . . ? C2 C3 C7 121.9(2) . . ? C2 C3 C4 120.7(2) . . ? C7 C3 C4 117.4(2) . . ? O4 C4 C3 109.59(18) . . ? O4 C4 C5 110.81(17) . . ? C3 C4 C5 110.12(19) . . ? O4 C4 H4 108.8 . . ? C3 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? C4 O4 H4A 109.5 . . ? O5 C5 C6 107.84(19) . . ? O5 C5 C4 106.44(16) . . ? C6 C5 C4 109.05(16) . . ? O5 C5 H5 111.1 . . ? C6 C5 H5 111.1 . . ? C4 C5 H5 111.1 . . ? C8 O5 C5 119.57(17) . . ? F6 C6 C5 111.25(17) . . ? F6 C6 C1 109.7(2) . . ? C5 C6 C1 110.85(18) . . ? F6 C6 H6 108.3 . . ? C5 C6 H6 108.3 . . ? C1 C6 H6 108.3 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O8 C8 O5 125.60(19) . . ? O8 C8 C9 124.87(18) . . ? O5 C8 C9 109.52(16) . . ? O9 C9 C8 107.17(15) . . ? O9 C9 C10 106.10(16) . . ? C8 C9 C10 118.57(16) . . ? O9 C9 C14 102.19(14) . . ? C8 C9 C14 117.11(18) . . ? C10 C9 C14 104.04(16) . . ? C13 O9 C9 105.91(14) . . ? C9 C10 C11 101.41(17) . . ? C9 C10 H10A 111.5 . . ? C11 C10 H10A 111.5 . . ? C9 C10 H10B 111.5 . . ? C11 C10 H10B 111.5 . . ? H10A C10 H10B 109.3 . . ? C10 C11 C12 103.57(17) . . ? C10 C11 H11A 111.0 . . ? C12 C11 H11A 111.0 . . ? C10 C11 H11B 111.0 . . ? C12 C11 H11B 111.0 . . ? H11A C11 H11B 109.0 . . ? C17 C12 C13 114.60(17) . . ? C17 C12 C11 115.35(19) . . ? C13 C12 C11 102.22(17) . . ? C17 C12 C14 119.28(19) . . ? C13 C12 C14 99.82(16) . . ? C11 C12 C14 103.05(16) . . ? O13 C13 O9 121.72(19) . . ? O13 C13 C12 130.65(19) . . ? O9 C13 C12 107.58(15) . . ? C15 C14 C16 109.01(19) . . ? C15 C14 C12 114.87(17) . . ? C16 C14 C12 113.17(16) . . ? C15 C14 C9 113.82(17) . . ? C16 C14 C9 114.24(16) . . ? C12 C14 C9 90.96(15) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 175.2(2) . . . . ? C6 C1 C2 C3 -5.7(3) . . . . ? C1 C2 C3 C7 179.7(2) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 O4 -148.1(2) . . . . ? C7 C3 C4 O4 33.1(3) . . . . ? C2 C3 C4 C5 -25.9(3) . . . . ? C7 C3 C4 C5 155.2(2) . . . . ? O4 C4 C5 O5 60.6(2) . . . . ? C3 C4 C5 O5 -60.8(2) . . . . ? O4 C4 C5 C6 176.67(18) . . . . ? C3 C4 C5 C6 55.3(2) . . . . ? C6 C5 O5 C8 130.18(19) . . . . ? C4 C5 O5 C8 -112.9(2) . . . . ? O5 C5 C6 F6 -68.3(2) . . . . ? C4 C5 C6 F6 176.54(18) . . . . ? O5 C5 C6 C1 54.2(2) . . . . ? C4 C5 C6 C1 -61.0(2) . . . . ? O1 C1 C6 F6 -21.4(3) . . . . ? C2 C1 C6 F6 159.39(18) . . . . ? O1 C1 C6 C5 -144.7(2) . . . . ? C2 C1 C6 C5 36.1(2) . . . . ? C5 O5 C8 O8 -11.6(3) . . . . ? C5 O5 C8 C9 167.69(18) . . . . ? O8 C8 C9 O9 -40.9(3) . . . . ? O5 C8 C9 O9 139.83(17) . . . . ? O8 C8 C9 C10 -160.8(2) . . . . ? O5 C8 C9 C10 19.9(2) . . . . ? O8 C8 C9 C14 73.1(3) . . . . ? O5 C8 C9 C14 -106.2(2) . . . . ? C8 C9 O9 C13 159.77(17) . . . . ? C10 C9 O9 C13 -72.62(19) . . . . ? C14 C9 O9 C13 36.1(2) . . . . ? O9 C9 C10 C11 69.12(18) . . . . ? C8 C9 C10 C11 -170.41(17) . . . . ? C14 C9 C10 C11 -38.25(19) . . . . ? C9 C10 C11 C12 2.1(2) . . . . ? C10 C11 C12 C17 166.28(18) . . . . ? C10 C11 C12 C13 -68.70(19) . . . . ? C10 C11 C12 C14 34.56(19) . . . . ? C9 O9 C13 O13 176.8(2) . . . . ? C9 O9 C13 C12 -1.0(2) . . . . ? C17 C12 C13 O13 19.5(4) . . . . ? C11 C12 C13 O13 -106.0(3) . . . . ? C14 C12 C13 O13 148.2(3) . . . . ? C17 C12 C13 O9 -163.05(19) . . . . ? C11 C12 C13 O9 71.4(2) . . . . ? C14 C12 C13 O9 -34.4(2) . . . . ? C17 C12 C14 C15 -66.8(3) . . . . ? C13 C12 C14 C15 167.64(19) . . . . ? C11 C12 C14 C15 62.5(2) . . . . ? C17 C12 C14 C16 59.3(2) . . . . ? C13 C12 C14 C16 -66.3(2) . . . . ? C11 C12 C14 C16 -171.40(17) . . . . ? C17 C12 C14 C9 176.25(19) . . . . ? C13 C12 C14 C9 50.70(16) . . . . ? C11 C12 C14 C9 -54.41(16) . . . . ? O9 C9 C14 C15 -171.04(17) . . . . ? C8 C9 C14 C15 72.2(2) . . . . ? C10 C9 C14 C15 -60.8(2) . . . . ? O9 C9 C14 C16 62.9(2) . . . . ? C8 C9 C14 C16 -53.9(2) . . . . ? C10 C9 C14 C16 173.13(16) . . . . ? O9 C9 C14 C12 -53.19(16) . . . . ? C8 C9 C14 C12 -169.92(16) . . . . ? C10 C9 C14 C12 57.08(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.131 _refine_diff_density_rms 0.029 #============================================================================ data_4iR _database_code_depnum_ccdc_archive 'CCDC 852570' #TrackingRef '4iR.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 Cl O3' _chemical_formula_sum 'C7 H9 Cl O3' _chemical_formula_weight 176.59 _chemical_absolute_configuration ad 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.125(2) _cell_length_b 4.8704(15) _cell_length_c 14.100(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.283(6) _cell_angle_gamma 90.00 _cell_volume 832.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 12.67 _exptl_crystal_description prisms _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.414 _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 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 'Bruker P4 diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2129 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0585 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2024 _reflns_number_gt 1400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0631P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(13) _refine_ls_number_reflns 2024 _refine_ls_number_parameters 205 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1266 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 C1A C 0.3081(4) 0.2241(13) 0.7671(4) 0.0564(15) Uani 1 1 d . . . O1A O 0.2390(3) 0.0406(11) 0.7589(3) 0.0827(14) Uani 1 1 d . . . C2A C 0.3704(4) 0.3170(15) 0.6863(3) 0.0595(15) Uani 1 1 d . . . H2A H 0.3500 0.2532 0.6260 0.071 Uiso 1 1 calc R . . C3A C 0.4542(4) 0.4872(12) 0.6958(3) 0.0489(13) Uani 1 1 d . . . Cl3A Cl 0.52108(13) 0.6021(5) 0.59754(10) 0.0895(6) Uani 1 1 d . . . C4A C 0.4948(4) 0.6043(12) 0.7889(3) 0.0502(13) Uani 1 1 d . . . H4A H 0.4701 0.7954 0.7930 0.060 Uiso 1 1 calc R . . O4A O 0.6117(2) 0.5984(9) 0.7947(3) 0.0660(11) Uani 1 1 d . . . H4A' H 0.6355 0.7550 0.8022 0.099 Uiso 1 1 calc R . . C5A C 0.4529(4) 0.4471(12) 0.8722(4) 0.0489(13) Uani 1 1 d . . . H5A H 0.4645 0.5583 0.9297 0.059 Uiso 1 1 calc R . . O5A O 0.5112(3) 0.1941(8) 0.8845(2) 0.0547(10) Uani 1 1 d . . . H5A' H 0.5777 0.2220 0.8816 0.082 Uiso 1 1 calc R . . C6A C 0.3297(4) 0.3753(13) 0.8603(3) 0.0581(16) Uani 1 1 d . . . H6A H 0.2895 0.5496 0.8553 0.070 Uiso 1 1 calc R . . C7A C 0.2857(5) 0.2230(19) 0.9455(4) 0.087(2) Uani 1 1 d . . . H7A1 H 0.2084 0.1876 0.9348 0.131 Uiso 1 1 calc R . . H7A2 H 0.2968 0.3334 1.0014 0.131 Uiso 1 1 calc R . . H7A3 H 0.3244 0.0522 0.9538 0.131 Uiso 1 1 calc R . . C1B C 0.7941(4) 1.1745(12) 0.7678(4) 0.0495(13) Uani 1 1 d . . . O1B O 0.7454(3) 1.0484(9) 0.8286(3) 0.0699(11) Uani 1 1 d . . . C2B C 0.7565(4) 1.1647(13) 0.6681(4) 0.0538(14) Uani 1 1 d . . . H2B H 0.6903 1.0776 0.6514 0.065 Uiso 1 1 calc R . . C3B C 0.8152(4) 1.2778(13) 0.6011(3) 0.0515(14) Uani 1 1 d . . . Cl3B Cl 0.76691(13) 1.2764(6) 0.48365(10) 0.0962(7) Uani 1 1 d . . . C4B C 0.9244(4) 1.4187(11) 0.6190(3) 0.0461(13) Uani 1 1 d . . . H4B H 0.9121 1.6173 0.6218 0.055 Uiso 1 1 calc R . . O4B O 0.9983(3) 1.3624(9) 0.5460(3) 0.0642(11) Uani 1 1 d . . . H4B' H 1.0044 1.4990 0.5126 0.096 Uiso 1 1 calc R . . C5B C 0.9756(4) 1.3243(12) 0.7133(3) 0.0490(13) Uani 1 1 d . . . H5B H 1.0412 1.4351 0.7293 0.059 Uiso 1 1 calc R . . O5B O 1.0062(3) 1.0394(8) 0.7075(3) 0.0577(10) Uani 1 1 d . . . H5B' H 1.0736 1.0265 0.7067 0.086 Uiso 1 1 calc R . . C6B C 0.8931(4) 1.3515(13) 0.7915(3) 0.0521(14) Uani 1 1 d . . . H6B H 0.8676 1.5425 0.7913 0.062 Uiso 1 1 calc R . . C7B C 0.9430(5) 1.291(2) 0.8917(4) 0.091(2) Uani 1 1 d . . . H7B1 H 0.8871 1.3128 0.9375 0.137 Uiso 1 1 calc R . . H7B2 H 1.0024 1.4170 0.9059 0.137 Uiso 1 1 calc R . . H7B3 H 0.9706 1.1065 0.8941 0.137 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 C1A 0.045(3) 0.053(4) 0.070(3) 0.000(3) -0.022(3) 0.010(3) O1A 0.061(2) 0.081(4) 0.104(3) 0.008(3) -0.026(2) -0.014(3) C2A 0.074(3) 0.057(4) 0.046(3) -0.005(3) -0.018(3) 0.011(4) C3A 0.052(3) 0.042(3) 0.053(3) 0.001(3) -0.006(2) 0.007(3) Cl3A 0.0906(11) 0.1143(17) 0.0636(8) 0.0177(10) 0.0054(8) 0.0029(12) C4A 0.052(3) 0.037(3) 0.060(3) -0.009(3) -0.010(2) 0.005(3) O4A 0.0482(19) 0.058(3) 0.091(3) 0.000(3) -0.0070(19) -0.003(2) C5A 0.051(3) 0.043(3) 0.051(3) -0.016(3) -0.004(2) 0.008(3) O5A 0.0515(18) 0.058(3) 0.0537(18) 0.0015(19) -0.0076(16) 0.007(2) C6A 0.048(3) 0.062(4) 0.065(3) -0.007(3) 0.003(2) 0.011(3) C7A 0.070(4) 0.110(7) 0.083(4) -0.006(5) 0.018(3) -0.009(5) C1B 0.041(2) 0.046(3) 0.062(3) 0.007(3) 0.006(2) 0.006(3) O1B 0.058(2) 0.068(3) 0.085(2) 0.018(3) 0.0134(19) -0.001(2) C2B 0.031(2) 0.055(4) 0.074(3) -0.005(3) -0.007(2) -0.006(3) C3B 0.047(3) 0.051(4) 0.057(3) -0.003(3) -0.004(2) 0.010(3) Cl3B 0.0781(10) 0.145(2) 0.0633(8) -0.0120(11) -0.0199(7) 0.0215(12) C4B 0.053(3) 0.029(3) 0.057(3) -0.003(3) 0.010(2) 0.000(3) O4B 0.070(2) 0.053(3) 0.072(2) 0.003(2) 0.0275(19) 0.003(2) C5B 0.039(2) 0.035(3) 0.072(3) -0.006(3) -0.004(2) -0.006(3) O5B 0.0374(17) 0.042(2) 0.093(3) -0.001(2) -0.0036(17) 0.0040(18) C6B 0.050(3) 0.051(4) 0.055(3) -0.008(3) 0.001(2) -0.004(3) C7B 0.085(4) 0.124(7) 0.063(3) -0.010(5) -0.012(3) -0.004(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1A O1A 1.227(7) . ? C1A C2A 1.464(8) . ? C1A C6A 1.519(7) . ? C2A C3A 1.314(8) . ? C2A H2A 0.9300 . ? C3A C4A 1.496(7) . ? C3A Cl3A 1.726(5) . ? C4A O4A 1.418(5) . ? C4A C5A 1.507(7) . ? C4A H4A 0.9800 . ? O4A H4A' 0.8200 . ? C5A O5A 1.428(6) . ? C5A C6A 1.537(7) . ? C5A H5A 0.9800 . ? O5A H5A' 0.8200 . ? C6A C7A 1.526(8) . ? C6A H6A 0.9800 . ? C7A H7A1 0.9600 . ? C7A H7A2 0.9600 . ? C7A H7A3 0.9600 . ? C1B O1B 1.225(6) . ? C1B C2B 1.461(7) . ? C1B C6B 1.504(7) . ? C2B C3B 1.325(7) . ? C2B H2B 0.9300 . ? C3B C4B 1.504(7) . ? C3B Cl3B 1.735(5) . ? C4B O4B 1.418(6) . ? C4B C5B 1.515(7) . ? C4B H4B 0.9800 . ? O4B H4B' 0.8200 . ? C5B O5B 1.439(7) . ? C5B C6B 1.525(6) . ? C5B H5B 0.9800 . ? O5B H5B' 0.8200 . ? C6B C7B 1.542(7) . ? C6B H6B 0.9800 . ? C7B H7B1 0.9600 . ? C7B H7B2 0.9600 . ? C7B H7B3 0.9600 . ? 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 O1A C1A C2A 121.6(5) . . ? O1A C1A C6A 121.8(5) . . ? C2A C1A C6A 116.5(5) . . ? C3A C2A C1A 122.5(5) . . ? C3A C2A H2A 118.8 . . ? C1A C2A H2A 118.8 . . ? C2A C3A C4A 123.8(5) . . ? C2A C3A Cl3A 120.6(4) . . ? C4A C3A Cl3A 115.6(4) . . ? O4A C4A C3A 109.6(4) . . ? O4A C4A C5A 108.2(4) . . ? C3A C4A C5A 112.4(5) . . ? O4A C4A H4A 108.9 . . ? C3A C4A H4A 108.9 . . ? C5A C4A H4A 108.9 . . ? C4A O4A H4A' 109.5 . . ? O5A C5A C4A 110.7(4) . . ? O5A C5A C6A 106.9(5) . . ? C4A C5A C6A 112.7(4) . . ? O5A C5A H5A 108.8 . . ? C4A C5A H5A 108.8 . . ? C6A C5A H5A 108.8 . . ? C5A O5A H5A' 109.5 . . ? C1A C6A C7A 113.0(6) . . ? C1A C6A C5A 109.8(4) . . ? C7A C6A C5A 113.1(4) . . ? C1A C6A H6A 106.8 . . ? C7A C6A H6A 106.8 . . ? C5A C6A H6A 106.8 . . ? C6A C7A H7A1 109.5 . . ? C6A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C6A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? O1B C1B C2B 121.1(5) . . ? O1B C1B C6B 122.2(4) . . ? C2B C1B C6B 116.7(4) . . ? C3B C2B C1B 121.1(4) . . ? C3B C2B H2B 119.5 . . ? C1B C2B H2B 119.5 . . ? C2B C3B C4B 124.4(4) . . ? C2B C3B Cl3B 120.5(4) . . ? C4B C3B Cl3B 115.0(4) . . ? O4B C4B C3B 111.6(4) . . ? O4B C4B C5B 109.2(4) . . ? C3B C4B C5B 109.6(4) . . ? O4B C4B H4B 108.8 . . ? C3B C4B H4B 108.8 . . ? C5B C4B H4B 108.8 . . ? C4B O4B H4B' 109.5 . . ? O5B C5B C4B 109.9(4) . . ? O5B C5B C6B 107.6(5) . . ? C4B C5B C6B 110.5(4) . . ? O5B C5B H5B 109.6 . . ? C4B C5B H5B 109.6 . . ? C6B C5B H5B 109.6 . . ? C5B O5B H5B' 109.5 . . ? C1B C6B C5B 109.2(4) . . ? C1B C6B C7B 112.1(5) . . ? C5B C6B C7B 113.7(4) . . ? C1B C6B H6B 107.2 . . ? C5B C6B H6B 107.2 . . ? C7B C6B H6B 107.2 . . ? C6B C7B H7B1 109.5 . . ? C6B C7B H7B2 109.5 . . ? H7B1 C7B H7B2 109.5 . . ? C6B C7B H7B3 109.5 . . ? H7B1 C7B H7B3 109.5 . . ? H7B2 C7B H7B3 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A C1A C2A C3A -171.1(5) . . . . ? C6A C1A C2A C3A 11.6(8) . . . . ? C1A C2A C3A C4A -0.2(9) . . . . ? C1A C2A C3A Cl3A -177.1(5) . . . . ? C2A C3A C4A O4A 137.2(5) . . . . ? Cl3A C3A C4A O4A -45.7(6) . . . . ? C2A C3A C4A C5A 16.8(7) . . . . ? Cl3A C3A C4A C5A -166.1(4) . . . . ? O4A C4A C5A O5A -45.5(5) . . . . ? C3A C4A C5A O5A 75.7(5) . . . . ? O4A C4A C5A C6A -165.1(4) . . . . ? C3A C4A C5A C6A -44.0(6) . . . . ? O1A C1A C6A C7A 17.6(7) . . . . ? C2A C1A C6A C7A -165.1(5) . . . . ? O1A C1A C6A C5A 145.0(5) . . . . ? C2A C1A C6A C5A -37.7(7) . . . . ? O5A C5A C6A C1A -67.5(6) . . . . ? C4A C5A C6A C1A 54.3(6) . . . . ? O5A C5A C6A C7A 59.8(6) . . . . ? C4A C5A C6A C7A -178.4(5) . . . . ? O1B C1B C2B C3B -173.1(5) . . . . ? C6B C1B C2B C3B 8.3(8) . . . . ? C1B C2B C3B C4B 1.4(9) . . . . ? C1B C2B C3B Cl3B -177.4(4) . . . . ? C2B C3B C4B O4B 141.7(5) . . . . ? Cl3B C3B C4B O4B -39.4(6) . . . . ? C2B C3B C4B C5B 20.5(8) . . . . ? Cl3B C3B C4B C5B -160.6(4) . . . . ? O4B C4B C5B O5B -54.9(5) . . . . ? C3B C4B C5B O5B 67.7(5) . . . . ? O4B C4B C5B C6B -173.5(4) . . . . ? C3B C4B C5B C6B -50.9(6) . . . . ? O1B C1B C6B C5B 142.7(5) . . . . ? C2B C1B C6B C5B -38.7(7) . . . . ? O1B C1B C6B C7B 15.9(8) . . . . ? C2B C1B C6B C7B -165.6(5) . . . . ? O5B C5B C6B C1B -59.3(5) . . . . ? C4B C5B C6B C1B 60.7(6) . . . . ? O5B C5B C6B C7B 66.7(6) . . . . ? C4B C5B C6B C7B -173.3(6) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.212 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.047