# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_(E)-3aa _database_code_depnum_ccdc_archive 'CCDC 922527' #TrackingRef '17332_web_deposit_cif_file_0_WilliamRaven_1359554922.(E)-3aa (E)-3ad.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point unk _chemical_formula_moiety 'C15 H15 F3 O3' _chemical_formula_sum 'C15 H15 F3 O3' _chemical_formula_weight 300.27 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8832(11) _cell_length_b 7.3687(8) _cell_length_c 19.706(2) _cell_angle_alpha 90 _cell_angle_beta 100.199(2) _cell_angle_gamma 90 _cell_volume 1412.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2 _cell_measurement_theta_max 26.66 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.412 _exptl_crystal_F_000 624 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.300 _exptl_absorpt_coefficient_mu 0.123 _shelx_estimated_absorpt_T_min 0.958 _shelx_estimated_absorpt_T_max 0.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6904 _exptl_absorpt_correction_T_max 0.7454 _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 'Incoatec microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16404 _diffrn_reflns_av_unetI/netI 0.0232 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.094 _diffrn_reflns_theta_max 26.572 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 2948 _reflns_number_gt 2561 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.6863P] 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 2948 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0888 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.33168(10) 0.81980(12) 0.18642(5) 0.0315(2) Uani 1 1 d . . . . . F2 F 0.24038(10) 0.83321(13) 0.07883(5) 0.0357(2) Uani 1 1 d . . . . . F3 F 0.45013(9) 0.74665(12) 0.10918(5) 0.0308(2) Uani 1 1 d . . . . . O1 O 0.29551(10) 0.45742(14) 0.06285(5) 0.0218(2) Uani 1 1 d . . . . . O2 O 0.61873(10) 0.13961(14) 0.17043(5) 0.0250(2) Uani 1 1 d . . . . . O3 O 0.66522(10) 0.04924(14) 0.06772(5) 0.0227(2) Uani 1 1 d . . . . . C1 C 0.13102(14) 0.52464(18) 0.14107(7) 0.0187(3) Uani 1 1 d . . . . . C2 C 0.03046(15) 0.44107(19) 0.09304(7) 0.0225(3) Uani 1 1 d . . . . . H2 H 0.0527 0.3966 0.0511 0.027 Uiso 1 1 calc R U . . . C3 C -0.10234(15) 0.4222(2) 0.10607(8) 0.0268(3) Uani 1 1 d . . . . . H3 H -0.1710 0.3664 0.0728 0.032 Uiso 1 1 calc R U . . . C4 C -0.13500(15) 0.4846(2) 0.16750(8) 0.0274(3) Uani 1 1 d . . . . . H4 H -0.2257 0.4708 0.1766 0.033 Uiso 1 1 calc R U . . . C5 C -0.03458(15) 0.5673(2) 0.21555(8) 0.0269(3) Uani 1 1 d . . . . . H5 H -0.0570 0.6109 0.2576 0.032 Uiso 1 1 calc R U . . . C6 C 0.09801(15) 0.5871(2) 0.20300(7) 0.0227(3) Uani 1 1 d . . . . . H6 H 0.1664 0.6430 0.2364 0.027 Uiso 1 1 calc R U . . . C7 C 0.27628(14) 0.54042(19) 0.12822(6) 0.0183(3) Uani 1 1 d . . . . . C8 C 0.38852(14) 0.41060(18) 0.16781(7) 0.0177(3) Uani 1 1 d . . . . . H8 H 0.4712 0.4773 0.1921 0.021 Uiso 1 1 calc R U . . . C9 C 0.40281(13) 0.35143(19) 0.09626(7) 0.0187(3) Uani 1 1 d . . . . . C10 C 0.32457(15) 0.7366(2) 0.12579(7) 0.0237(3) Uani 1 1 d . . . . . C11 C 0.33844(15) 0.26715(19) 0.21288(7) 0.0224(3) Uani 1 1 d . . . . . H11A H 0.2580 0.2054 0.1867 0.034 Uiso 1 1 calc R U . . . H11B H 0.3132 0.3250 0.2537 0.034 Uiso 1 1 calc R U . . . H11C H 0.4118 0.1785 0.2274 0.034 Uiso 1 1 calc R U . . . C12 C 0.48091(14) 0.2433(2) 0.06596(7) 0.0215(3) Uani 1 1 d . . . . . H12 H 0.4647 0.2320 0.0172 0.026 Uiso 1 1 calc R U . . . C13 C 0.59230(13) 0.14109(19) 0.10783(7) 0.0197(3) Uani 1 1 d . . . . . C14 C 0.77896(16) -0.0579(2) 0.10354(8) 0.0285(3) Uani 1 1 d . . . . . H14A H 0.7446 -0.1733 0.1198 0.034 Uiso 1 1 calc R U . . . H14B H 0.8277 0.0095 0.1441 0.034 Uiso 1 1 calc R U . . . C15 C 0.87446(16) -0.0953(2) 0.05427(8) 0.0279(3) Uani 1 1 d . . . . . H15A H 0.8240 -0.1557 0.0132 0.042 Uiso 1 1 calc R U . . . H15B H 0.9493 -0.1740 0.0764 0.042 Uiso 1 1 calc R U . . . H15C H 0.9127 0.0194 0.0409 0.042 Uiso 1 1 calc R U . . . 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 F1 0.0425(5) 0.0202(4) 0.0340(5) -0.0058(4) 0.0125(4) -0.0041(4) F2 0.0356(5) 0.0301(5) 0.0410(5) 0.0183(4) 0.0062(4) 0.0068(4) F3 0.0273(5) 0.0281(5) 0.0395(5) 0.0054(4) 0.0132(4) -0.0025(4) O1 0.0228(5) 0.0281(5) 0.0147(5) -0.0012(4) 0.0035(4) 0.0076(4) O2 0.0245(5) 0.0311(6) 0.0195(5) -0.0017(4) 0.0038(4) 0.0062(4) O3 0.0221(5) 0.0265(5) 0.0202(5) -0.0011(4) 0.0054(4) 0.0076(4) C1 0.0198(7) 0.0163(6) 0.0196(6) 0.0026(5) 0.0028(5) 0.0037(5) C2 0.0254(7) 0.0192(7) 0.0226(7) -0.0009(5) 0.0032(6) 0.0032(6) C3 0.0239(7) 0.0218(7) 0.0327(8) -0.0003(6) -0.0005(6) -0.0010(6) C4 0.0202(7) 0.0257(8) 0.0376(8) 0.0066(6) 0.0091(6) 0.0027(6) C5 0.0265(8) 0.0308(8) 0.0250(7) 0.0014(6) 0.0089(6) 0.0050(6) C6 0.0233(7) 0.0238(7) 0.0208(7) -0.0009(6) 0.0036(5) 0.0022(6) C7 0.0221(7) 0.0191(7) 0.0139(6) -0.0014(5) 0.0039(5) 0.0036(5) C8 0.0182(6) 0.0176(7) 0.0172(6) -0.0011(5) 0.0029(5) 0.0021(5) C9 0.0174(6) 0.0205(7) 0.0176(6) 0.0010(5) 0.0013(5) -0.0002(5) C10 0.0252(7) 0.0220(7) 0.0249(7) 0.0044(6) 0.0076(6) 0.0035(6) C11 0.0264(7) 0.0208(7) 0.0213(7) 0.0040(6) 0.0075(6) 0.0045(6) C12 0.0223(7) 0.0258(7) 0.0165(6) -0.0039(5) 0.0031(5) 0.0012(6) C13 0.0187(7) 0.0201(7) 0.0211(7) -0.0031(5) 0.0058(5) -0.0008(5) C14 0.0275(8) 0.0325(8) 0.0265(7) 0.0071(6) 0.0079(6) 0.0132(7) C15 0.0263(8) 0.0294(8) 0.0293(8) 0.0011(6) 0.0086(6) 0.0084(6) _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 F1 C10 1.3337(17) . ? F2 C10 1.3352(17) . ? F3 C10 1.3403(17) . ? O1 C9 1.3859(16) . ? O1 C7 1.4685(15) . ? O2 C13 1.2149(16) . ? O3 C13 1.3432(16) . ? O3 C14 1.4505(17) . ? C1 C2 1.3892(19) . ? C1 C6 1.3958(19) . ? C1 C7 1.5058(19) . ? C2 C3 1.388(2) . ? C2 H2 0.9500 . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C10 1.526(2) . ? C7 C8 1.5645(18) . ? C8 C9 1.5062(18) . ? C8 C11 1.5188(19) . ? C8 H8 1.0000 . ? C9 C12 1.3231(19) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.4622(19) . ? C12 H12 0.9500 . ? C14 C15 1.495(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C9 O1 C7 91.43(9) . . ? C13 O3 C14 115.98(11) . . ? C2 C1 C6 119.48(13) . . ? C2 C1 C7 120.53(12) . . ? C6 C1 C7 119.93(12) . . ? C3 C2 C1 120.27(13) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 120.17(14) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.57(14) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 120.70(14) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 119.81(13) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? O1 C7 C1 113.00(11) . . ? O1 C7 C10 106.10(11) . . ? C1 C7 C10 113.03(11) . . ? O1 C7 C8 89.56(9) . . ? C1 C7 C8 118.80(11) . . ? C10 C7 C8 113.39(11) . . ? C9 C8 C11 116.12(11) . . ? C9 C8 C7 83.45(9) . . ? C11 C8 C7 116.20(11) . . ? C9 C8 H8 112.7 . . ? C11 C8 H8 112.7 . . ? C7 C8 H8 112.7 . . ? C12 C9 O1 125.70(12) . . ? C12 C9 C8 139.08(13) . . ? O1 C9 C8 95.21(10) . . ? F1 C10 F2 107.67(12) . . ? F1 C10 F3 106.81(12) . . ? F2 C10 F3 106.96(11) . . ? F1 C10 C7 111.99(11) . . ? F2 C10 C7 111.53(12) . . ? F3 C10 C7 111.61(12) . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 C13 119.78(12) . . ? C9 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? O2 C13 O3 123.49(12) . . ? O2 C13 C12 125.64(12) . . ? O3 C13 C12 110.86(11) . . ? O3 C14 C15 107.96(12) . . ? O3 C14 H14A 110.1 . . ? C15 C14 H14A 110.1 . . ? O3 C14 H14B 110.1 . . ? C15 C14 H14B 110.1 . . ? H14A C14 H14B 108.4 . . ? 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 . . ? _refine_diff_density_max 0.299 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.041 data_(E)-3ad _database_code_depnum_ccdc_archive 'CCDC 922528' #TrackingRef '17332_web_deposit_cif_file_0_WilliamRaven_1359554922.(E)-3aa (E)-3ad.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point unk _chemical_formula_moiety 'C13 H13 F3 O3 S' _chemical_formula_sum 'C13 H13 F3 O3 S' _chemical_formula_weight 306.29 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_H-M_alt 'C c' _space_group_name_Hall 'C -2yc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 12.4906(15) _cell_length_b 12.0630(14) _cell_length_c 9.5353(12) _cell_angle_alpha 90 _cell_angle_beta 103.731(2) _cell_angle_gamma 90 _cell_volume 1395.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2 _cell_measurement_theta_max 30.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_F_000 632 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.480 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.280 _exptl_absorpt_coefficient_mu 0.270 _shelx_estimated_absorpt_T_min 0.881 _shelx_estimated_absorpt_T_max 0.928 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6792 _exptl_absorpt_correction_T_max 0.7461 _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 'Incoatec microsource' _diffrn_radiation_monochromator 'multilayer optics' _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8352 _diffrn_reflns_av_unetI/netI 0.0467 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.381 _diffrn_reflns_theta_max 30.556 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.933 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.933 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.900 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 3852 _reflns_number_gt 3578 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.925 _reflns_Friedel_fraction_max 0.866 _reflns_Friedel_fraction_full 0.998 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'SMART (Bruker, 2001)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0432P)^2^+1.1370P] 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 x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.05(5) _chemical_absolute_configuration ? _refine_ls_number_reflns 3852 _refine_ls_number_parameters 183 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0488 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1088 _refine_ls_wR_factor_gt 0.1029 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.092 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.36800(9) 0.75055(7) 0.01318(10) 0.02356(18) Uani 1 1 d . . . . . F1 F 0.24349(17) 0.39502(16) 0.1701(2) 0.0256(4) Uani 1 1 d . . . . . F2 F 0.39839(18) 0.45482(17) 0.2995(2) 0.0259(5) Uani 1 1 d . . . . . F3 F 0.37212(17) 0.44346(17) 0.0675(2) 0.0248(4) Uani 1 1 d . . . . . O1 O 0.19283(19) 0.5922(2) 0.0271(2) 0.0192(5) Uani 1 1 d . . . . . O2 O -0.0433(2) 0.5999(2) 0.2779(3) 0.0259(5) Uani 1 1 d . . . . . O3 O -0.1744(2) 0.5707(2) 0.0736(3) 0.0246(5) Uani 1 1 d . . . . . C1 C 0.4903(3) 0.8101(3) 0.0943(4) 0.0225(7) Uani 1 1 d . . . . . H1 H 0.5259 0.8646 0.0494 0.027 Uiso 1 1 calc R U . . . C2 C 0.5319(3) 0.7716(3) 0.2300(4) 0.0239(7) Uani 1 1 d . . . . . H2 H 0.5994 0.7971 0.2896 0.029 Uiso 1 1 calc R U . . . C3 C 0.4643(3) 0.6883(3) 0.2759(4) 0.0224(7) Uani 1 1 d . . . . . H3 H 0.4803 0.6523 0.3671 0.027 Uiso 1 1 calc R U . . . C4 C 0.3703(3) 0.6695(3) 0.1624(3) 0.0174(6) Uani 1 1 d . . . . . C5 C 0.2801(3) 0.5880(3) 0.1608(3) 0.0172(6) Uani 1 1 d . . . . . C6 C 0.1918(3) 0.6107(3) 0.2501(3) 0.0165(6) Uani 1 1 d . . . . . H6 H 0.1858 0.5487 0.3175 0.020 Uiso 1 1 calc R U . . . C7 C 0.1123(3) 0.5993(3) 0.1048(3) 0.0169(6) Uani 1 1 d . . . . . C8 C 0.3239(3) 0.4691(3) 0.1746(4) 0.0194(6) Uani 1 1 d . . . . . C9 C 0.1962(3) 0.7241(3) 0.3204(4) 0.0235(7) Uani 1 1 d . . . . . H9A H 0.1998 0.7816 0.2491 0.035 Uiso 1 1 calc R U . . . H9B H 0.2616 0.7289 0.4007 0.035 Uiso 1 1 calc R U . . . H9C H 0.1299 0.7351 0.3569 0.035 Uiso 1 1 calc R U . . . C10 C 0.0046(3) 0.5927(3) 0.0497(4) 0.0195(6) Uani 1 1 d . . . . . H10 H -0.0239 0.5899 -0.0519 0.023 Uiso 1 1 calc R U . . . C11 C -0.0703(3) 0.5898(3) 0.1478(4) 0.0196(6) Uani 1 1 d . . . . . C12 C -0.2545(3) 0.5584(4) 0.1602(5) 0.0339(9) Uani 1 1 d . . . . . H12A H -0.2671 0.6305 0.2031 0.041 Uiso 1 1 calc R U . . . H12B H -0.2276 0.5048 0.2393 0.041 Uiso 1 1 calc R U . . . C13 C -0.3591(3) 0.5174(4) 0.0629(5) 0.0381(10) Uani 1 1 d . . . . . H13A H -0.3843 0.5705 -0.0158 0.057 Uiso 1 1 calc R U . . . H13B H -0.4156 0.5095 0.1181 0.057 Uiso 1 1 calc R U . . . H13C H -0.3460 0.4453 0.0226 0.057 Uiso 1 1 calc R U . . . 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 S1 0.0249(4) 0.0237(3) 0.0216(3) 0.0020(3) 0.0046(3) -0.0050(3) F1 0.0226(11) 0.0216(10) 0.0346(11) -0.0005(8) 0.0105(9) -0.0061(8) F2 0.0260(11) 0.0243(10) 0.0244(10) 0.0049(8) 0.0003(8) 0.0022(8) F3 0.0226(10) 0.0271(10) 0.0270(10) -0.0039(8) 0.0105(8) -0.0004(8) O1 0.0152(11) 0.0265(12) 0.0154(10) 0.0002(8) 0.0027(8) -0.0031(9) O2 0.0190(12) 0.0370(14) 0.0227(11) -0.0032(10) 0.0070(9) -0.0034(10) O3 0.0149(11) 0.0323(13) 0.0259(12) 0.0008(10) 0.0034(9) -0.0013(10) C1 0.0247(17) 0.0201(15) 0.0243(16) -0.0016(12) 0.0090(13) -0.0053(13) C2 0.0195(16) 0.0297(18) 0.0233(16) -0.0060(13) 0.0062(13) -0.0068(13) C3 0.0186(15) 0.0195(15) 0.0325(17) -0.0061(13) 0.0130(13) -0.0106(12) C4 0.0190(15) 0.0188(14) 0.0152(13) 0.0009(11) 0.0056(11) -0.0029(11) C5 0.0165(14) 0.0212(14) 0.0138(12) -0.0001(11) 0.0037(10) -0.0037(11) C6 0.0142(14) 0.0195(14) 0.0156(13) 0.0001(10) 0.0034(11) -0.0026(11) C7 0.0182(15) 0.0176(14) 0.0157(13) 0.0003(11) 0.0054(11) -0.0032(11) C8 0.0166(14) 0.0223(15) 0.0205(14) -0.0024(12) 0.0070(12) -0.0046(12) C9 0.0211(17) 0.0273(16) 0.0227(16) -0.0050(13) 0.0064(13) -0.0022(13) C10 0.0167(15) 0.0233(15) 0.0176(13) 0.0008(12) 0.0025(11) -0.0021(12) C11 0.0142(15) 0.0200(14) 0.0242(15) 0.0007(12) 0.0039(12) -0.0001(11) C12 0.0163(17) 0.050(2) 0.036(2) -0.0049(18) 0.0089(15) -0.0044(16) C13 0.0156(17) 0.049(2) 0.049(2) -0.002(2) 0.0069(16) -0.0052(17) _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 S1 C1 1.700(4) . ? S1 C4 1.721(3) . ? F1 C8 1.338(4) . ? F2 C8 1.337(4) . ? F3 C8 1.339(4) . ? O1 C7 1.386(4) . ? O1 C5 1.468(4) . ? O2 C11 1.212(4) . ? O3 C11 1.344(4) . ? O3 C12 1.448(5) . ? C1 C2 1.357(5) . ? C1 H1 0.9500 . ? C2 C3 1.445(5) . ? C2 H2 0.9500 . ? C3 C4 1.414(5) . ? C3 H3 0.9500 . ? C4 C5 1.492(4) . ? C5 C8 1.530(5) . ? C5 C6 1.568(4) . ? C6 C7 1.507(4) . ? C6 C9 1.519(5) . ? C6 H6 1.0000 . ? C7 C10 1.325(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.472(5) . ? C10 H10 0.9500 . ? C12 C13 1.496(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 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 C1 S1 C4 91.57(17) . . ? C7 O1 C5 91.2(2) . . ? C11 O3 C12 115.5(3) . . ? C2 C1 S1 112.8(3) . . ? C2 C1 H1 123.6 . . ? S1 C1 H1 123.6 . . ? C1 C2 C3 114.1(3) . . ? C1 C2 H2 122.9 . . ? C3 C2 H2 122.9 . . ? C4 C3 C2 108.6(3) . . ? C4 C3 H3 125.7 . . ? C2 C3 H3 125.7 . . ? C3 C4 C5 127.0(3) . . ? C3 C4 S1 112.9(2) . . ? C5 C4 S1 120.1(2) . . ? O1 C5 C4 112.9(2) . . ? O1 C5 C8 106.5(2) . . ? C4 C5 C8 111.3(3) . . ? O1 C5 C6 89.6(2) . . ? C4 C5 C6 120.4(3) . . ? C8 C5 C6 113.5(2) . . ? C7 C6 C9 115.7(3) . . ? C7 C6 C5 83.1(2) . . ? C9 C6 C5 116.1(3) . . ? C7 C6 H6 112.9 . . ? C9 C6 H6 112.9 . . ? C5 C6 H6 112.9 . . ? C10 C7 O1 125.5(3) . . ? C10 C7 C6 139.1(3) . . ? O1 C7 C6 95.3(2) . . ? F1 C8 F2 107.5(3) . . ? F1 C8 F3 107.0(3) . . ? F2 C8 F3 107.8(3) . . ? F1 C8 C5 111.9(3) . . ? F2 C8 C5 110.9(3) . . ? F3 C8 C5 111.6(3) . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 C11 119.2(3) . . ? C7 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? O2 C11 O3 123.8(3) . . ? O2 C11 C10 125.7(3) . . ? O3 C11 C10 110.5(3) . . ? O3 C12 C13 107.5(3) . . ? O3 C12 H12A 110.2 . . ? C13 C12 H12A 110.2 . . ? O3 C12 H12B 110.2 . . ? C13 C12 H12B 110.2 . . ? H12A C12 H12B 108.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _refine_diff_density_max 0.414 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.072