Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address 'Fredrik K Wallner' ; Department of Chemistry, Ume\%a University, SE-901 87 Ume\%a, Sweden. ; 'Sara Spjut' ; Department of Chemistry, Ume\%a University, SE-901 87 Ume\%a, Sweden ; D.Bostrom ; Energy Technology and Thermal Process Chemistry, Department of Applied Fhysics a ; 'Mikael Elofsson' ; Department of Chemistry, Ume\%a University, SE-901 87 Ume\%a, Sweden ; _publ_contact_author_address ; Department of Chemistry, Ume\%a University, SE-901 87 Ume\%a, Sweden ; _publ_contact_author_name 'Mikael Elofsson' _publ_section_title ; Synthesis and evaluation of 2-(2-fluoro-4-hydroxymethyl-5-methoxy-phenoxy) acetic acid as linker in solid-phase synthesis monitored by gel-phase 19F NMR spectroscopy ; _publ_contact_author_email MIKAEL.ELOFSSON@CHEM.UMU.SE # Attachment 'compound_13.cif' # CIF Copied by cif2cif, version 0.0.8 - beta ( 2 Apr 98) data_compound13 _database_code_depnum_ccdc_archive 'CCDC 644117' _audit_creation_method maXus _chemical_compound_source 'Local laboratory' _exptl_crystal_description Plate _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.01 _exptl_crystal_colour Colourless _cell_measurement_temperature 298 _refine_ls_hydrogen_treatment constr # Submission details _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.08440 _diffrn_orient_matrix_UB_12 0.07231 _diffrn_orient_matrix_UB_13 0.04443 _diffrn_orient_matrix_UB_21 -0.01780 _diffrn_orient_matrix_UB_22 0.05076 _diffrn_orient_matrix_UB_23 -0.04880 _diffrn_orient_matrix_UB_31 -0.03246 _diffrn_orient_matrix_UB_32 0.01868 _diffrn_orient_matrix_UB_33 0.03127 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 498.475 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z '-X+ 1/2,-Y+ 1/2,+Z+ 1/2' '+X+ 1/2,+Y+ 1/2,-Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X+ 1/2,+Y+ 1/2,+Z' '-X,+Y,-Z+ 1/2' '+X,-Y,+Z+ 1/2' _symmetry_space_group_name_H-M 'P b c n ' _symmetry_space_group_name_Hall '-P 2n 2ab ' _symmetry_cell_setting Orthorhombic _chemical_formula_moiety 'C24 H28 F2 O9 ' _chemical_formula_sum 'C24 H28 F2 O9 ' _chemical_name_systematic ; ? ; _cell_length_a 13.7696(5) _cell_length_b 8.3551(2) _cell_length_c 20.4951(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2357.89(12) _diffrn_reflns_number 5390 _diffrn_reflns_theta_max 27.61 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_full 27.61 _cell_measurement_reflns_used 3063 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 27.485 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.117 _reflns_number_total 2703 _reflns_number_gt 1735 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement '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^)+(0.0495P)^2^+0.8759P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2703 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1389 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 O1 O 0.5000 0.9802(2) -0.2500 0.0475(5) Uani 1 2 d S . . O2 O 0.49479(11) 0.68328(19) 0.03277(7) 0.0512(4) Uani 1 1 d . . . O3 O 0.64036(11) 0.4862(2) 0.14988(7) 0.0514(4) Uani 1 1 d . . . O4 O 0.66911(11) 0.9657(2) -0.13824(7) 0.0574(5) Uani 1 1 d . . . F5 F 0.33060(9) 0.7898(2) -0.01924(7) 0.0668(4) Uani 1 1 d . . . C6 C 0.55936(16) 0.5415(3) 0.12244(10) 0.0447(5) Uani 1 1 d . . . C7 C 0.58825(15) 0.8213(3) -0.05185(10) 0.0437(5) Uani 1 1 d . . . O8 O 0.48032(12) 0.5252(2) 0.14496(9) 0.0680(5) Uani 1 1 d . . . C9 C 0.41604(15) 0.8323(3) -0.04816(10) 0.0450(5) Uani 1 1 d . . . C10 C 0.58688(15) 0.9184(3) -0.10669(9) 0.0422(5) Uani 1 1 d . . . C11 C 0.58318(16) 0.6275(3) 0.06028(11) 0.0467(5) Uani 1 1 d . . . C12 C 0.50193(15) 0.7773(3) -0.02184(10) 0.0420(5) Uani 1 1 d . . . C13 C 0.49986(15) 0.9732(3) -0.13319(9) 0.0414(5) Uani 1 1 d . . . C14 C 0.41415(15) 0.9278(3) -0.10227(10) 0.0446(5) Uani 1 1 d . . . C15 C 0.49840(17) 1.0774(3) -0.19266(10) 0.0444(5) Uani 1 1 d . . . C16 C 0.62780(18) 0.3997(3) 0.21137(11) 0.0544(6) Uani 1 1 d . . . C17 C 0.7236(2) 0.3311(4) 0.22933(13) 0.0689(7) Uani 1 1 d . . . C18 C 0.76036(17) 0.9266(4) -0.11024(12) 0.0658(7) Uani 1 1 d . . . H7 H 0.6490 0.7843 -0.0344 0.052 Uiso 1 1 d R . . H11A H 0.6143 0.5560 0.0302 0.056 Uiso 1 1 d R . . H11B H 0.6251 0.7169 0.0689 0.056 Uiso 1 1 d R . . H14 H 0.3532 0.9644 -0.1195 0.054 Uiso 1 1 d R . . H15A H 0.5543 1.1461 -0.1923 0.053 Uiso 1 1 d R . . H15B H 0.4405 1.1415 -0.1925 0.053 Uiso 1 1 d R . . H16A H 0.6057 0.4723 0.2445 0.065 Uiso 1 1 d R . . H16B H 0.5808 0.3161 0.2056 0.065 Uiso 1 1 d R . . H17A H 0.7180 0.2731 0.2696 0.083 Uiso 1 1 d R . . H17B H 0.7699 0.4161 0.2344 0.083 Uiso 1 1 d R . . H17C H 0.7450 0.2599 0.1955 0.083 Uiso 1 1 d R . . H18A H 0.8117 0.9669 -0.1374 0.079 Uiso 1 1 d R . . H18B H 0.7661 0.8125 -0.1065 0.079 Uiso 1 1 d R . . H18C H 0.7648 0.9742 -0.0677 0.079 Uiso 1 1 d 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 O1 0.0644(14) 0.0463(11) 0.0318(10) 0.000 -0.0042(9) 0.000 O2 0.0437(9) 0.0627(10) 0.0473(8) 0.0113(8) -0.0001(7) 0.0007(8) O3 0.0434(8) 0.0667(10) 0.0442(8) 0.0096(8) 0.0003(7) -0.0003(8) O4 0.0387(8) 0.0836(12) 0.0498(9) 0.0149(9) 0.0017(7) -0.0021(8) F5 0.0413(8) 0.0917(11) 0.0675(9) 0.0183(8) 0.0092(6) -0.0010(7) C6 0.0442(13) 0.0484(13) 0.0415(11) -0.0043(10) 0.0004(10) -0.0025(10) C7 0.0372(11) 0.0540(13) 0.0400(11) -0.0023(10) -0.0040(9) 0.0030(10) O8 0.0440(10) 0.0965(14) 0.0635(11) 0.0212(10) 0.0082(8) 0.0043(9) C9 0.0377(12) 0.0546(13) 0.0429(11) -0.0032(10) 0.0049(9) -0.0012(10) C10 0.0379(11) 0.0533(13) 0.0352(10) -0.0029(9) -0.0001(9) -0.0025(10) C11 0.0413(12) 0.0536(13) 0.0453(11) 0.0013(10) -0.0018(10) -0.0006(10) C12 0.0458(12) 0.0454(11) 0.0348(10) -0.0019(9) 0.0011(9) -0.0024(10) C13 0.0427(11) 0.0480(11) 0.0336(10) -0.0067(9) -0.0017(9) 0.0011(10) C14 0.0382(12) 0.0543(13) 0.0413(11) -0.0035(10) -0.0056(9) 0.0052(10) C15 0.0471(12) 0.0477(11) 0.0383(10) -0.0045(10) -0.0025(9) 0.0023(10) C16 0.0554(14) 0.0667(15) 0.0409(11) 0.0069(11) 0.0015(11) -0.0014(12) C17 0.0734(19) 0.0755(17) 0.0579(14) 0.0120(14) -0.0074(13) 0.0087(15) C18 0.0384(13) 0.094(2) 0.0650(15) 0.0116(15) -0.0017(12) -0.0034(13) _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 O1 C15 1.429(2) . ? O1 C15 1.429(2) . ? O2 C12 1.371(2) . ? O2 C11 1.420(3) . ? O3 C6 1.332(3) . ? O3 C16 1.463(3) . ? O4 C10 1.362(2) . ? O4 C18 1.419(3) . ? F5 C9 1.365(2) . ? C6 O8 1.190(3) . ? C6 C11 1.499(3) . ? C7 C10 1.386(3) . ? C7 C12 1.388(3) . ? C9 C14 1.366(3) . ? C9 C12 1.379(3) . ? C10 C13 1.393(3) . ? C13 C14 1.392(3) . ? C13 C15 1.498(3) . ? C16 C17 1.485(4) . ? C7 H7 0.9600 . ? C11 H11A 0.9599 . ? C11 H11B 0.9599 . ? C14 H14 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C16 H16A 0.9599 . ? C16 H16B 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9599 . ? C18 H18B 0.9600 . ? C18 H18C 0.9601 . ? 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 C15 O1 C15 110.7(2) . . ? C12 O2 C11 116.78(16) . . ? C6 O3 C16 115.84(17) . . ? C10 O4 C18 118.51(18) . . ? O8 C6 O3 124.2(2) . . ? O8 C6 C11 125.8(2) . . ? O3 C6 C11 109.99(18) . . ? C10 C7 C12 120.17(19) . . ? F5 C9 C14 119.23(19) . . ? F5 C9 C12 118.86(19) . . ? C14 C9 C12 121.91(19) . . ? O4 C10 C7 122.90(19) . . ? O4 C10 C13 115.76(18) . . ? C7 C10 C13 121.34(19) . . ? O2 C11 C6 107.89(17) . . ? O2 C12 C9 116.68(18) . . ? O2 C12 C7 125.09(19) . . ? C9 C12 C7 118.23(19) . . ? C14 C13 C10 117.53(18) . . ? C14 C13 C15 121.15(19) . . ? C10 C13 C15 121.32(19) . . ? C9 C14 C13 120.8(2) . . ? O1 C15 C13 109.77(17) . . ? O3 C16 C17 107.42(19) . . ? C10 C7 H7 120.1 . . ? C12 C7 H7 119.7 . . ? O2 C11 H11A 109.3 . . ? C6 C11 H11A 110.2 . . ? O2 C11 H11B 109.5 . . ? C6 C11 H11B 110.4 . . ? H11A C11 H11B 109.5 . . ? C9 C14 H14 120.1 . . ? C13 C14 H14 119.1 . . ? O1 C15 H15A 109.5 . . ? C13 C15 H15A 109.3 . . ? O1 C15 H15B 109.5 . . ? C13 C15 H15B 109.4 . . ? H15A C15 H15B 109.5 . . ? O3 C16 H16A 109.6 . . ? C17 C16 H16A 110.5 . . ? O3 C16 H16B 109.4 . . ? C17 C16 H16B 110.4 . . ? H16A C16 H16B 109.5 . . ? C16 C17 H17A 109.7 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.4 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 H18A 109.7 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.2 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.153 _refine_diff_density_min -0.161 _refine_diff_density_rms 0.039 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ; data_compound_11 _database_code_depnum_ccdc_archive 'CCDC 644118' _audit_creation_method maXus _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All diagrams and calculations were performed using maXus (Bruker Nonius, Delft & MacScience, Japan). ; _chemical_compound_source 'Local laboratory' _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _cell_measurement_temperature 100 _refine_ls_hydrogen_treatment constr _diffrn_measurement_device KappaCCD _computing_data_collection KappaCCD _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.73 loop_ _diffrn_radiation_wavelength 0.71074 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_UB_11 0.12285 _diffrn_orient_matrix_UB_12 -0.16440 _diffrn_orient_matrix_UB_13 -0.04292 _diffrn_orient_matrix_UB_21 -0.04316 _diffrn_orient_matrix_UB_22 -0.00546 _diffrn_orient_matrix_UB_23 -0.07853 _diffrn_orient_matrix_UB_31 0.03174 _diffrn_orient_matrix_UB_32 0.02950 _diffrn_orient_matrix_UB_33 -0.01109 _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_special_details ; ? ; _chemical_formula_weight 258.245 _diffrn_radiation_type ' MoK\a' loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z -X,-Y,-Z _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' _symmetry_cell_setting Triclinic _chemical_formula_moiety 'C12 H15 F O5 ' _chemical_formula_sum 'C12 H15 F O5 ' _chemical_name_systematic ; ? ; _cell_length_a 4.7854(6) _cell_length_b 11.316(2) _cell_length_c 22.705(3) _cell_angle_alpha 80.348(8) _cell_angle_beta 86.525(10) _cell_angle_gamma 86.318(7) _cell_volume 1208.0(3) _diffrn_reflns_number 8117 _cell_measurement_reflns_used 4077 _diffrn_measurement_method CCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? 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' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.120 _reflns_number_total 4249 _reflns_number_gt 3114 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement '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^)+(0.0407P)^2^+1.2430P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0089(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4249 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1734 _refine_ls_wR_factor_gt 0.1526 _refine_ls_goodness_of_fit_ref 1.246 _refine_ls_restrained_S_all 1.246 _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 F1 F 1.1304(4) 0.35763(19) 0.60084(9) 0.0320(6) Uani 1 1 d . . . O2 O 0.6202(5) 0.4122(2) 0.12463(10) 0.0199(6) Uani 1 1 d . . . O3 O 0.9657(5) 0.5546(2) 0.15138(10) 0.0215(6) Uani 1 1 d . . . O4 O 0.0029(5) -0.0672(2) 0.15546(10) 0.0221(6) Uani 1 1 d . . . O5 O 0.2789(5) 0.1290(2) 0.01002(10) 0.0225(6) Uani 1 1 d . . . O6 O 1.1546(5) 0.5991(2) 0.05782(11) 0.0263(7) Uani 1 1 d . . . O7 O 0.3180(5) 0.1666(2) 0.45487(11) 0.0270(7) Uani 1 1 d . . . O8 O 0.4818(5) 0.3311(2) 0.48188(11) 0.0270(7) Uani 1 1 d . . . O9 O 0.8375(5) 0.2164(2) 0.55099(10) 0.0227(6) Uani 1 1 d . . . C10 C 0.9916(7) 0.5457(3) 0.09381(16) 0.0174(8) Uani 1 1 d . . . F11 F 0.2901(4) 0.32224(18) 0.21573(8) 0.0272(6) Uani 1 1 d . . . C12 C -0.0647(7) 0.0296(3) 0.10885(16) 0.0224(9) Uani 1 1 d . . . C13 C 0.1139(7) 0.1337(3) 0.10944(15) 0.0185(8) Uani 1 1 d . . . O14 O 1.5068(5) 0.1034(2) 0.78425(10) 0.0225(6) Uani 1 1 d . . . C15 C 0.6788(7) 0.1408(3) 0.52325(15) 0.0205(9) Uani 1 1 d . . . C16 C 1.2081(7) -0.0049(3) 0.66221(15) 0.0215(9) Uani 1 1 d . . . C17 C 0.4556(7) 0.2757(3) 0.06298(15) 0.0175(8) Uani 1 1 d . . . C18 C 1.3317(7) 0.1942(4) 0.66672(16) 0.0253(9) Uani 1 1 d . . . O19 O 1.2429(5) -0.1242(2) 0.68611(11) 0.0278(7) Uani 1 1 d . . . C20 C 0.4717(8) 0.1684(3) -0.03896(16) 0.0271(10) Uani 1 1 d . . . C21 C 0.1161(7) 0.1851(3) 0.16127(16) 0.0203(9) Uani 1 1 d . . . C22 C 0.4587(7) 0.3225(3) 0.11570(16) 0.0178(8) Uani 1 1 d . . . C23 C 0.2785(8) 0.4097(4) 0.44588(17) 0.0305(10) Uani 1 1 d . . . C24 C 0.7984(7) 0.4611(3) 0.07518(15) 0.0174(8) Uani 1 1 d . . . C25 C 1.0067(7) 0.1616(3) 0.59524(15) 0.0208(9) Uani 1 1 d . . . C26 C 0.2853(7) 0.1818(3) 0.06021(15) 0.0170(8) Uani 1 1 d . . . C27 C 0.4739(7) 0.2140(4) 0.48250(16) 0.0213(9) Uani 1 1 d . . . C28 C 0.2858(7) 0.2757(3) 0.16428(15) 0.0198(9) Uani 1 1 d . . . C29 C 1.3576(7) 0.0722(4) 0.68909(16) 0.0241(9) Uani 1 1 d . . . C30 C 1.0705(8) -0.2052(3) 0.66506(17) 0.0293(10) Uani 1 1 d . . . C31 C 1.5377(8) 0.0256(4) 0.74063(17) 0.0323(10) Uani 1 1 d . . . C32 C 1.0339(7) 0.0388(3) 0.61555(15) 0.0219(9) Uani 1 1 d . . . C33 C 1.1575(7) 0.2372(3) 0.62128(16) 0.0229(9) Uani 1 1 d . . . C34 C 1.1603(8) 0.6307(3) 0.17198(16) 0.0252(9) Uani 1 1 d . . . C35 C 1.0732(10) 0.6341(4) 0.23645(18) 0.0457(12) Uani 1 1 d . . . C36 C 0.3770(9) 0.4316(4) 0.38107(17) 0.0350(11) Uani 1 1 d . . . H4 H -0.1832 -0.0909 0.1760 0.027 Uiso 1 1 d R . . H12A H -0.2588 0.0544 0.1145 0.027 Uiso 1 1 d R . . H12B H -0.0347 0.0022 0.0711 0.027 Uiso 1 1 d R . . H14 H 1.6763 0.0843 0.8068 0.027 Uiso 1 1 d R . . H15A H 0.5773 0.0882 0.5535 0.025 Uiso 1 1 d R . . H15B H 0.8029 0.0941 0.5002 0.025 Uiso 1 1 d R . . H17 H 0.5711 0.3089 0.0289 0.021 Uiso 1 1 d R . . H18 H 1.4343 0.2494 0.6836 0.030 Uiso 1 1 d R . . H20A H 0.4473 0.1254 -0.0712 0.033 Uiso 1 1 d R . . H20B H 0.6602 0.1534 -0.0262 0.033 Uiso 1 1 d R . . H20C H 0.4370 0.2528 -0.0523 0.033 Uiso 1 1 d R . . H21 H -0.0032 0.1554 0.1954 0.024 Uiso 1 1 d R . . H23A H 0.2552 0.4850 0.4602 0.037 Uiso 1 1 d R . . H23B H 0.1020 0.3726 0.4496 0.037 Uiso 1 1 d R . . H24A H 0.9070 0.3973 0.0601 0.021 Uiso 1 1 d R . . H24B H 0.6850 0.5043 0.0443 0.021 Uiso 1 1 d R . . H30A H 1.1132 -0.2855 0.6849 0.035 Uiso 1 1 d R . . H30B H 0.8767 -0.1832 0.6733 0.035 Uiso 1 1 d R . . H30C H 1.1056 -0.2012 0.6227 0.035 Uiso 1 1 d R . . H31A H 1.7304 0.0203 0.7264 0.039 Uiso 1 1 d R . . H31B H 1.4815 -0.0527 0.7587 0.039 Uiso 1 1 d R . . H32 H 0.9368 -0.0171 0.5979 0.026 Uiso 1 1 d R . . H34A H 1.3471 0.5956 0.1680 0.030 Uiso 1 1 d R . . H34B H 1.1486 0.7091 0.1479 0.030 Uiso 1 1 d R . . H35A H 1.1966 0.6831 0.2524 0.055 Uiso 1 1 d R . . H35B H 1.0827 0.5544 0.2591 0.055 Uiso 1 1 d R . . H35C H 0.8846 0.6679 0.2389 0.055 Uiso 1 1 d R . . H36A H 0.2401 0.4830 0.3585 0.042 Uiso 1 1 d R . . H36B H 0.5524 0.4696 0.3769 0.042 Uiso 1 1 d R . . H36C H 0.4012 0.3567 0.3664 0.042 Uiso 1 1 d 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 F1 0.0343(13) 0.0274(14) 0.0362(13) -0.0090(11) -0.0108(10) 0.0035(10) O2 0.0198(13) 0.0196(14) 0.0204(14) -0.0032(11) 0.0053(11) -0.0070(11) O3 0.0233(14) 0.0224(15) 0.0200(14) -0.0053(11) 0.0010(11) -0.0062(11) O4 0.0172(13) 0.0181(14) 0.0277(14) 0.0065(11) -0.0032(11) -0.0010(11) O5 0.0238(14) 0.0235(15) 0.0208(14) -0.0046(11) 0.0041(12) -0.0078(11) O6 0.0309(15) 0.0268(16) 0.0216(15) -0.0030(12) 0.0041(12) -0.0132(12) O7 0.0247(15) 0.0325(17) 0.0242(15) -0.0029(12) -0.0069(12) -0.0038(12) O8 0.0281(15) 0.0250(17) 0.0277(15) -0.0014(12) -0.0109(12) 0.0027(12) O9 0.0215(14) 0.0250(15) 0.0206(14) -0.0013(11) -0.0042(11) 0.0015(11) C10 0.016(2) 0.017(2) 0.018(2) -0.0003(16) -0.0009(17) 0.0026(16) F11 0.0309(12) 0.0320(13) 0.0196(11) -0.0059(10) 0.0026(9) -0.0091(10) C12 0.017(2) 0.026(2) 0.024(2) 0.0003(17) -0.0040(16) -0.0048(16) C13 0.0127(19) 0.018(2) 0.023(2) 0.0007(16) -0.0028(16) 0.0008(15) O14 0.0171(13) 0.0307(16) 0.0199(14) -0.0037(12) -0.0042(11) -0.0008(11) C15 0.017(2) 0.025(2) 0.019(2) -0.0024(17) -0.0018(16) -0.0032(16) C16 0.0158(19) 0.028(2) 0.018(2) 0.0019(17) 0.0031(16) 0.0018(17) C17 0.0146(19) 0.015(2) 0.021(2) 0.0001(16) 0.0005(16) 0.0015(15) C18 0.017(2) 0.035(3) 0.027(2) -0.0135(19) -0.0022(17) 0.0029(18) O19 0.0265(15) 0.0287(17) 0.0257(15) 0.0038(12) -0.0050(12) 0.0004(12) C20 0.030(2) 0.028(2) 0.024(2) -0.0074(18) 0.0052(18) -0.0078(18) C21 0.017(2) 0.022(2) 0.020(2) 0.0020(17) 0.0006(16) -0.0023(17) C22 0.0103(18) 0.014(2) 0.028(2) 0.0000(16) -0.0021(16) -0.0016(15) C23 0.029(2) 0.027(2) 0.034(2) -0.0014(19) -0.0129(19) 0.0086(18) C24 0.0173(19) 0.019(2) 0.0154(19) -0.0018(16) 0.0002(16) 0.0003(16) C25 0.0147(19) 0.030(2) 0.0158(19) -0.0017(17) 0.0019(16) 0.0033(17) C26 0.0157(19) 0.018(2) 0.0164(19) -0.0015(16) -0.0050(16) 0.0028(16) C27 0.017(2) 0.026(2) 0.020(2) -0.0049(17) 0.0024(17) -0.0011(17) C28 0.021(2) 0.022(2) 0.017(2) -0.0036(16) -0.0029(16) 0.0001(17) C29 0.0137(19) 0.037(3) 0.020(2) -0.0050(18) 0.0006(16) 0.0060(18) C30 0.029(2) 0.027(2) 0.029(2) 0.0000(18) 0.0018(18) -0.0001(19) C31 0.027(2) 0.045(3) 0.026(2) -0.014(2) -0.0021(18) 0.010(2) C32 0.016(2) 0.029(2) 0.019(2) -0.0031(17) 0.0032(16) -0.0009(17) C33 0.022(2) 0.021(2) 0.024(2) -0.0045(17) 0.0000(18) 0.0060(17) C34 0.023(2) 0.023(2) 0.032(2) -0.0093(18) -0.0006(18) -0.0065(17) C35 0.065(3) 0.046(3) 0.030(2) -0.011(2) 0.003(2) -0.027(2) C36 0.033(2) 0.035(3) 0.033(2) 0.004(2) -0.006(2) 0.004(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 F1 C33 1.364(4) . ? O2 C22 1.363(4) . ? O2 C24 1.425(4) . ? O3 C10 1.325(4) . ? O3 C34 1.456(4) . ? O4 C12 1.426(4) . ? O5 C26 1.376(4) . ? O5 C20 1.431(4) . ? O6 C10 1.208(4) . ? O7 C27 1.208(4) . ? O8 C27 1.326(4) . ? O8 C23 1.465(4) . ? O9 C25 1.369(4) . ? O9 C15 1.423(4) . ? C10 C24 1.499(5) . ? F11 C28 1.361(4) . ? C12 C13 1.501(5) . ? C13 C21 1.398(5) . ? C13 C26 1.400(5) . ? O14 C31 1.427(4) . ? C15 C27 1.501(5) . ? C16 O19 1.371(4) . ? C16 C32 1.393(5) . ? C16 C29 1.399(5) . ? C17 C22 1.389(5) . ? C17 C26 1.391(5) . ? C18 C33 1.371(5) . ? C18 C29 1.389(5) . ? O19 C30 1.429(4) . ? C21 C28 1.361(5) . ? C22 C28 1.390(5) . ? C23 C36 1.502(5) . ? C25 C33 1.380(5) . ? C25 C32 1.389(5) . ? C29 C31 1.499(5) . ? C34 C35 1.503(5) . ? O4 H4 1.0103 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? O14 H14 0.9777 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C17 H17 0.9600 . ? C18 H18 0.9600 . ? C20 H20A 0.9599 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9601 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9601 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C32 H32 0.9601 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9601 . ? C35 H35C 0.9600 . ? C36 H36A 0.9599 . ? C36 H36B 0.9600 . ? C36 H36C 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 C22 O2 C24 116.4(3) . . ? C10 O3 C34 116.1(3) . . ? C26 O5 C20 117.2(3) . . ? C27 O8 C23 117.2(3) . . ? C25 O9 C15 117.1(3) . . ? O6 C10 O3 125.0(3) . . ? O6 C10 C24 120.7(3) . . ? O3 C10 C24 114.4(3) . . ? O4 C12 C13 111.2(3) . . ? C21 C13 C26 117.4(3) . . ? C21 C13 C12 119.6(3) . . ? C26 C13 C12 122.9(3) . . ? O9 C15 C27 110.8(3) . . ? O19 C16 C32 123.6(3) . . ? O19 C16 C29 114.9(3) . . ? C32 C16 C29 121.5(4) . . ? C22 C17 C26 119.7(3) . . ? C33 C18 C29 120.8(4) . . ? C16 O19 C30 117.2(3) . . ? C28 C21 C13 121.1(3) . . ? O2 C22 C17 125.4(3) . . ? O2 C22 C28 115.7(3) . . ? C17 C22 C28 118.8(3) . . ? O8 C23 C36 110.9(3) . . ? O2 C24 C10 110.5(3) . . ? O9 C25 C33 115.7(3) . . ? O9 C25 C32 125.4(3) . . ? C33 C25 C32 118.9(3) . . ? O5 C26 C17 122.6(3) . . ? O5 C26 C13 116.0(3) . . ? C17 C26 C13 121.4(3) . . ? O7 C27 O8 125.7(3) . . ? O7 C27 C15 121.1(3) . . ? O8 C27 C15 113.2(3) . . ? C21 C28 F11 120.1(3) . . ? C21 C28 C22 121.5(3) . . ? F11 C28 C22 118.4(3) . . ? C18 C29 C16 117.7(3) . . ? C18 C29 C31 120.9(4) . . ? C16 C29 C31 121.4(4) . . ? O14 C31 C29 110.4(3) . . ? C25 C32 C16 119.5(4) . . ? F1 C33 C18 119.9(3) . . ? F1 C33 C25 118.5(3) . . ? C18 C33 C25 121.6(4) . . ? O3 C34 C35 105.8(3) . . ? C12 O4 H4 105.1 . . ? O4 C12 H12A 108.4 . . ? C13 C12 H12A 109.6 . . ? O4 C12 H12B 108.9 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 109.5 . . ? C31 O14 H14 103.6 . . ? O9 C15 H15A 109.4 . . ? C27 C15 H15A 108.9 . . ? O9 C15 H15B 109.5 . . ? C27 C15 H15B 108.8 . . ? H15A C15 H15B 109.5 . . ? C22 C17 H17 119.3 . . ? C26 C17 H17 121.0 . . ? C33 C18 H18 119.3 . . ? C29 C18 H18 119.8 . . ? O5 C20 H20A 109.6 . . ? O5 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O5 C20 H20C 109.4 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C28 C21 H21 119.6 . . ? C13 C21 H21 119.3 . . ? O8 C23 H23A 109.0 . . ? C36 C23 H23A 109.2 . . ? O8 C23 H23B 109.3 . . ? C36 C23 H23B 108.9 . . ? H23A C23 H23B 109.5 . . ? O2 C24 H24A 109.5 . . ? C10 C24 H24A 109.4 . . ? O2 C24 H24B 109.0 . . ? C10 C24 H24B 108.9 . . ? H24A C24 H24B 109.5 . . ? O19 C30 H30A 109.6 . . ? O19 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O19 C30 H30C 109.3 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O14 C31 H31A 109.5 . . ? C29 C31 H31A 109.4 . . ? O14 C31 H31B 109.0 . . ? C29 C31 H31B 109.0 . . ? H31A C31 H31B 109.5 . . ? C25 C32 H32 121.5 . . ? C16 C32 H32 119.0 . . ? O3 C34 H34A 108.8 . . ? C35 C34 H34A 111.2 . . ? O3 C34 H34B 109.4 . . ? C35 C34 H34B 112.1 . . ? H34A C34 H34B 109.5 . . ? C34 C35 H35A 109.1 . . ? C34 C35 H35B 110.2 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.1 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C23 C36 H36A 109.3 . . ? C23 C36 H36B 109.4 . . ? H36A C36 H36B 109.5 . . ? C23 C36 H36C 109.8 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? _diffrn_reflns_theta_max 25.00 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.282 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.067 _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Moliterni, A.G.G & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. ;