# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Jonathan Percy' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE1 7RH UNITED KINGDOM ; _publ_contact_author_email JMP29@LE.AC.UK _publ_section_title ; Rapid syntheses of difluorinated analogues of(hydroxymethyl)conduritols ; loop_ _publ_author_name 'Jonathan Percy' 'John Fawcett' 'Ian H. Hillier' 'Andrew C. Moralee' 'Vittoria Salafia' ; M.A.Vincent ; data_6a _database_code_depnum_ccdc_archive 'CCDC 229969' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H19 Cl4 F2 N O5 Sn' _chemical_formula_weight 579.79 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' N N 0.0061 0.0033 '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' Sn Sn -0.6537 1.4246 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4879(11) _cell_length_b 18.8071(19) _cell_length_c 10.7203(11) _cell_angle_alpha 90.00 _cell_angle_beta 102.993(2) _cell_angle_gamma 90.00 _cell_volume 2060.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7168 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.39 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.869 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 1.802 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.80 _exptl_absorpt_correction_T_max 0.89 _exptl_absorpt_process_details ; absorption correction based on 5879 reflections (SADABS); Rint 0.034 before correction and 0.014 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10971 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4033 _reflns_number_gt 3761 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0328P)^2^+1.0826P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4033 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0254 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _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 Sn1 Sn 0.732849(17) 0.482949(9) 0.775439(15) 0.02270(7) Uani 1 1 d . . . Cl1 Cl 0.50709(7) 0.50333(4) 0.70984(8) 0.04142(18) Uani 1 1 d . . . Cl2 Cl 0.74585(7) 0.52387(3) 0.98742(6) 0.02899(15) Uani 1 1 d . . . Cl3 Cl 0.74903(7) 0.42475(4) 0.58570(6) 0.03208(16) Uani 1 1 d . . . Cl4 Cl 0.82018(9) 0.58959(4) 0.71858(7) 0.0439(2) Uani 1 1 d . . . F1 F 0.78495(15) 0.23688(8) 0.87737(14) 0.0310(3) Uani 1 1 d . . . F2 F 0.88786(17) 0.25825(9) 0.72809(14) 0.0376(4) Uani 1 1 d . . . N1 N 0.6762(2) 0.34931(11) 1.04422(19) 0.0230(4) Uani 1 1 d . . . O1 O 1.12119(18) 0.24508(10) 0.92390(18) 0.0307(4) Uani 1 1 d . . . O2 O 0.93782(17) 0.44521(9) 0.84473(16) 0.0230(4) Uani 1 1 d . . . O3 O 1.06855(18) 0.36946(9) 0.77628(17) 0.0286(4) Uani 1 1 d . . . O4 O 0.87694(16) 0.34858(9) 1.00860(15) 0.0189(3) Uani 1 1 d . . . O5 O 0.70338(16) 0.37991(9) 0.84833(15) 0.0212(4) Uani 1 1 d . . . C1 C 1.0874(2) 0.29510(14) 1.0102(2) 0.0244(5) Uani 1 1 d . . . H1 H 1.1558 0.3319 1.0421 0.029 Uiso 1 1 calc R . . C2 C 0.9553(2) 0.32511(13) 0.9250(2) 0.0187(5) Uani 1 1 d . . . C3 C 0.9025(3) 0.25417(14) 0.8545(2) 0.0259(5) Uani 1 1 d . . . C4 C 1.0109(3) 0.20043(14) 0.9156(3) 0.0288(6) Uani 1 1 d . . . H4 H 1.0124 0.1555 0.8661 0.035 Uiso 1 1 calc R . . C5 C 1.0033(3) 0.19049(15) 1.0527(3) 0.0327(6) Uani 1 1 d . . . H5 H 0.9709 0.1503 1.0895 0.039 Uiso 1 1 calc R . . C6 C 1.0520(2) 0.25047(15) 1.1120(2) 0.0274(6) Uani 1 1 d . . . H6 H 1.0618 0.2621 1.1999 0.033 Uiso 1 1 calc R . . C7 C 0.9840(2) 0.38575(13) 0.8422(2) 0.0211(5) Uani 1 1 d . . . C8 C 1.1058(3) 0.42550(16) 0.6945(3) 0.0352(7) Uani 1 1 d . . . H8A H 1.0274 0.4431 0.6326 0.042 Uiso 1 1 calc R . . H8B H 1.1469 0.4660 0.7477 0.042 Uiso 1 1 calc R . . C9 C 1.1970(5) 0.3944(2) 0.6277(4) 0.0737(13) Uani 1 1 d . . . H9A H 1.2719 0.3749 0.6899 0.111 Uiso 1 1 calc R . . H9B H 1.2275 0.4310 0.5761 0.111 Uiso 1 1 calc R . . H9C H 1.1536 0.3563 0.5716 0.111 Uiso 1 1 calc R . . C10 C 0.7476(2) 0.36033(12) 0.9620(2) 0.0200(5) Uani 1 1 d . . . C11 C 0.5366(3) 0.36802(15) 1.0106(3) 0.0313(6) Uani 1 1 d . . . H11A H 0.5235 0.4087 0.9506 0.038 Uiso 1 1 calc R . . H11B H 0.5085 0.3829 1.0889 0.038 Uiso 1 1 calc R . . C12 C 0.4536(3) 0.30654(18) 0.9499(3) 0.0426(7) Uani 1 1 d . . . H12A H 0.4763 0.2943 0.8687 0.064 Uiso 1 1 calc R . . H12B H 0.3610 0.3199 0.9338 0.064 Uiso 1 1 calc R . . H12C H 0.4695 0.2655 1.0075 0.064 Uiso 1 1 calc R . . C13 C 0.7291(3) 0.31724(14) 1.1705(2) 0.0275(6) Uani 1 1 d . . . H13A H 0.7965 0.2817 1.1627 0.033 Uiso 1 1 calc R . . H13B H 0.6580 0.2922 1.1994 0.033 Uiso 1 1 calc R . . C14 C 0.7889(3) 0.37190(16) 1.2694(3) 0.0362(7) Uani 1 1 d . . . H14A H 0.8641 0.3941 1.2447 0.054 Uiso 1 1 calc R . . H14B H 0.8178 0.3488 1.3528 0.054 Uiso 1 1 calc R . . H14C H 0.7236 0.4084 1.2748 0.054 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 Sn1 0.02818(12) 0.01641(10) 0.02192(10) 0.00021(6) 0.00226(7) 0.00266(7) Cl1 0.0323(4) 0.0400(4) 0.0452(4) -0.0026(3) -0.0055(3) 0.0135(3) Cl2 0.0336(4) 0.0256(3) 0.0277(3) -0.0068(2) 0.0065(3) 0.0021(3) Cl3 0.0427(4) 0.0311(3) 0.0225(3) -0.0043(2) 0.0073(3) -0.0057(3) Cl4 0.0725(6) 0.0200(3) 0.0382(4) 0.0048(3) 0.0100(4) -0.0070(3) F1 0.0280(8) 0.0266(8) 0.0383(8) -0.0050(7) 0.0071(7) -0.0065(7) F2 0.0497(11) 0.0363(9) 0.0270(8) -0.0078(7) 0.0090(7) -0.0039(8) N1 0.0221(11) 0.0233(11) 0.0259(10) 0.0016(8) 0.0101(9) 0.0024(9) O1 0.0288(10) 0.0258(9) 0.0412(11) -0.0019(8) 0.0161(8) 0.0033(8) O2 0.0237(9) 0.0172(9) 0.0282(9) 0.0020(7) 0.0058(7) -0.0009(7) O3 0.0352(11) 0.0243(9) 0.0317(10) 0.0058(8) 0.0193(8) 0.0013(8) O4 0.0181(9) 0.0203(8) 0.0193(8) -0.0009(6) 0.0066(6) 0.0012(7) O5 0.0226(9) 0.0179(8) 0.0230(8) 0.0013(7) 0.0046(7) 0.0017(7) C1 0.0236(13) 0.0246(13) 0.0264(12) 0.0010(10) 0.0086(10) 0.0044(11) C2 0.0198(12) 0.0179(11) 0.0203(11) -0.0003(9) 0.0085(9) -0.0003(10) C3 0.0273(14) 0.0249(13) 0.0276(13) -0.0070(10) 0.0110(11) -0.0046(11) C4 0.0324(15) 0.0188(12) 0.0380(15) -0.0013(11) 0.0139(12) 0.0026(11) C5 0.0271(14) 0.0260(14) 0.0470(16) 0.0105(12) 0.0127(12) 0.0054(12) C6 0.0212(13) 0.0358(15) 0.0255(13) 0.0098(11) 0.0060(10) 0.0101(12) C7 0.0228(13) 0.0210(12) 0.0197(11) -0.0012(9) 0.0055(9) -0.0024(10) C8 0.0432(18) 0.0327(15) 0.0350(15) 0.0091(12) 0.0202(13) -0.0043(13) C9 0.098(3) 0.064(3) 0.081(3) 0.024(2) 0.068(3) 0.010(2) C10 0.0224(13) 0.0142(11) 0.0239(12) -0.0032(9) 0.0068(10) 0.0004(10) C11 0.0231(14) 0.0357(15) 0.0383(15) 0.0006(12) 0.0133(11) 0.0058(12) C12 0.0275(16) 0.055(2) 0.0459(17) -0.0069(15) 0.0103(13) -0.0049(14) C13 0.0298(14) 0.0288(14) 0.0273(13) 0.0070(11) 0.0134(11) 0.0038(12) C14 0.0385(17) 0.0420(17) 0.0285(14) -0.0033(12) 0.0084(12) 0.0016(14) _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 Sn1 O5 2.1378(16) . ? Sn1 O2 2.2268(17) . ? Sn1 Cl4 2.3418(7) . ? Sn1 Cl1 2.3450(8) . ? Sn1 Cl3 2.3494(7) . ? Sn1 Cl2 2.3740(7) . ? F1 C3 1.350(3) . ? F2 C3 1.332(3) . ? N1 C10 1.295(3) . ? N1 C11 1.469(3) . ? N1 C13 1.472(3) . ? O1 C4 1.416(3) . ? O1 C1 1.419(3) . ? O2 C7 1.221(3) . ? O3 C7 1.289(3) . ? O3 C8 1.478(3) . ? O4 C10 1.354(3) . ? O4 C2 1.416(3) . ? O5 C10 1.258(3) . ? C1 C6 1.488(4) . ? C1 C2 1.582(3) . ? C2 C7 1.517(3) . ? C2 C3 1.571(3) . ? C3 C4 1.551(4) . ? C4 C5 1.502(4) . ? C5 C6 1.338(4) . ? C8 C9 1.442(5) . ? C11 C12 1.505(4) . ? C13 C14 1.508(4) . ? 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 O5 Sn1 O2 78.30(6) . . ? O5 Sn1 Cl4 165.61(5) . . ? O2 Sn1 Cl4 87.43(5) . . ? O5 Sn1 Cl1 92.21(5) . . ? O2 Sn1 Cl1 170.42(5) . . ? Cl4 Sn1 Cl1 102.10(3) . . ? O5 Sn1 Cl3 86.48(5) . . ? O2 Sn1 Cl3 83.57(5) . . ? Cl4 Sn1 Cl3 93.73(3) . . ? Cl1 Sn1 Cl3 94.65(3) . . ? O5 Sn1 Cl2 85.75(5) . . ? O2 Sn1 Cl2 86.60(5) . . ? Cl4 Sn1 Cl2 91.71(3) . . ? Cl1 Sn1 Cl2 94.07(3) . . ? Cl3 Sn1 Cl2 168.53(2) . . ? C10 N1 C11 119.4(2) . . ? C10 N1 C13 122.4(2) . . ? C11 N1 C13 118.2(2) . . ? C4 O1 C1 96.54(19) . . ? C7 O2 Sn1 129.98(16) . . ? C7 O3 C8 117.5(2) . . ? C10 O4 C2 119.57(18) . . ? C10 O5 Sn1 124.58(15) . . ? O1 C1 C6 104.1(2) . . ? O1 C1 C2 100.06(19) . . ? C6 C1 C2 107.1(2) . . ? O4 C2 C7 110.85(19) . . ? O4 C2 C3 112.16(19) . . ? C7 C2 C3 116.86(19) . . ? O4 C2 C1 107.68(17) . . ? C7 C2 C1 110.0(2) . . ? C3 C2 C1 98.21(19) . . ? F2 C3 F1 107.3(2) . . ? F2 C3 C4 111.9(2) . . ? F1 C3 C4 112.3(2) . . ? F2 C3 C2 112.8(2) . . ? F1 C3 C2 110.78(19) . . ? C4 C3 C2 101.8(2) . . ? O1 C4 C5 103.6(2) . . ? O1 C4 C3 98.7(2) . . ? C5 C4 C3 107.4(2) . . ? C6 C5 C4 105.1(2) . . ? C5 C6 C1 105.0(2) . . ? O2 C7 O3 123.7(2) . . ? O2 C7 C2 122.9(2) . . ? O3 C7 C2 113.2(2) . . ? C9 C8 O3 107.4(3) . . ? O5 C10 N1 124.3(2) . . ? O5 C10 O4 121.7(2) . . ? N1 C10 O4 114.0(2) . . ? N1 C11 C12 111.7(2) . . ? N1 C13 C14 112.2(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.710 _refine_diff_density_min -0.336 _refine_diff_density_rms 0.077 #===END data_8 _database_code_depnum_ccdc_archive 'CCDC 229970' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 Br F2 N O5' _chemical_formula_weight 398.20 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' N N 0.0061 0.0033 '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' Br Br -0.2901 2.4595 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6660(9) _cell_length_b 8.0535(6) _cell_length_c 18.3629(14) _cell_angle_alpha 90.00 _cell_angle_beta 102.7150(10) _cell_angle_gamma 90.00 _cell_volume 1682.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4659 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 27.70 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 2.486 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.676 _exptl_absorpt_correction_T_max 0.801 _exptl_absorpt_process_details ; absorption correction based on 7337 reflections (SADABS); Rint 0.054 before correction and 0.026 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12743 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0303 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3310 _reflns_number_gt 2699 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0571P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3310 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.001 _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 Br1 Br 0.67030(3) -0.38044(4) 0.753021(15) 0.04654(13) Uani 1 1 d . . . F1 F 0.80343(12) -0.19050(17) 0.53549(7) 0.0348(3) Uani 1 1 d . . . F2 F 0.85032(12) -0.18126(17) 0.65611(8) 0.0362(3) Uani 1 1 d . . . N1 N 0.71564(18) 0.3015(2) 0.44357(10) 0.0279(4) Uani 1 1 d . A . O1 O 0.56275(14) -0.15055(19) 0.55434(9) 0.0279(4) Uani 1 1 d . A . O2 O 0.76350(19) 0.1640(2) 0.71405(10) 0.0451(5) Uani 1 1 d . . . O3 O 0.88640(17) 0.1821(2) 0.63625(10) 0.0436(5) Uani 1 1 d . . . O4 O 0.71729(14) 0.09009(17) 0.52133(8) 0.0239(3) Uani 1 1 d . A . O5 O 0.67548(16) 0.34794(19) 0.55773(9) 0.0316(4) Uani 1 1 d . A . C1 C 0.5871(2) -0.0040(3) 0.60070(12) 0.0268(5) Uani 1 1 d . A . H1 H 0.5312 0.0903 0.5854 0.032 Uiso 1 1 calc R . . C2 C 0.71499(19) 0.0300(3) 0.59378(11) 0.0228(5) Uani 1 1 d . . . C3 C 0.7603(2) -0.1526(3) 0.59625(12) 0.0256(5) Uani 1 1 d . A . C4 C 0.6509(2) -0.2546(3) 0.59860(12) 0.0272(5) Uani 1 1 d . . . H4 H 0.6517 -0.3730 0.5823 0.033 Uiso 1 1 calc R A . C5 C 0.6287(2) -0.2257(3) 0.67575(13) 0.0306(5) Uani 1 1 d . A . C6 C 0.5902(2) -0.0733(3) 0.67771(13) 0.0316(6) Uani 1 1 d . . . H6 H 0.5689 -0.0184 0.7186 0.038 Uiso 1 1 calc R A . C7 C 0.7889(2) 0.1362(3) 0.65566(13) 0.0311(6) Uani 1 1 d . A . C8 C 0.9398(14) 0.3236(19) 0.6902(10) 0.0620(13) Uani 0.35 1 d P A 1 H8A H 0.8817 0.3534 0.7200 0.074 Uiso 0.35 1 calc PR A 1 H8B H 1.0097 0.2787 0.7253 0.074 Uiso 0.35 1 calc PR A 1 C9 C 0.9674(9) 0.4439(14) 0.6649(6) 0.0620(13) Uani 0.35 1 d P A 1 H9A H 0.9897 0.4184 0.6177 0.093 Uiso 0.35 1 calc PR A 1 H9B H 1.0345 0.4933 0.6998 0.093 Uiso 0.35 1 calc PR A 1 H9C H 0.9016 0.5223 0.6557 0.093 Uiso 0.35 1 calc PR A 1 C8' C 0.9733(6) 0.2783(10) 0.6865(5) 0.0620(13) Uani 0.65 1 d P A 2 H8'1 H 0.9338 0.3437 0.7195 0.074 Uiso 0.65 1 calc PR A 2 H8'2 H 1.0290 0.2016 0.7184 0.074 Uiso 0.65 1 calc PR A 2 C9' C 1.0354(5) 0.3845(7) 0.6515(3) 0.0620(13) Uani 0.65 1 d P A 2 H9'1 H 1.0878 0.3205 0.6271 0.093 Uiso 0.65 1 calc PR A 2 H9'2 H 1.0821 0.4598 0.6884 0.093 Uiso 0.65 1 calc PR A 2 H9'3 H 0.9807 0.4493 0.6140 0.093 Uiso 0.65 1 calc PR A 2 C10 C 0.6998(2) 0.2571(3) 0.51041(12) 0.0257(5) Uani 1 1 d . . . C11 C 0.7459(2) 0.1829(3) 0.39032(13) 0.0350(6) Uani 1 1 d . . . H11A H 0.7196 0.2277 0.3392 0.042 Uiso 1 1 calc R A . H11B H 0.7031 0.0778 0.3931 0.042 Uiso 1 1 calc R . . C12 C 0.8754(3) 0.1471(4) 0.40467(19) 0.0533(8) Uani 1 1 d . A . H12A H 0.9184 0.2507 0.4022 0.080 Uiso 1 1 calc R . . H12B H 0.8909 0.0695 0.3669 0.080 Uiso 1 1 calc R . . H12C H 0.9013 0.0977 0.4544 0.080 Uiso 1 1 calc R . . C13 C 0.7149(2) 0.4793(3) 0.42618(14) 0.0379(6) Uani 1 1 d . . . H13A H 0.7579 0.4971 0.3860 0.045 Uiso 1 1 calc R A . H13B H 0.7571 0.5401 0.4709 0.045 Uiso 1 1 calc R . . C14 C 0.5939(3) 0.5497(4) 0.40198(17) 0.0525(8) Uani 1 1 d . A . H14A H 0.5510 0.4890 0.3581 0.079 Uiso 1 1 calc R . . H14B H 0.5991 0.6672 0.3893 0.079 Uiso 1 1 calc R . . H14C H 0.5523 0.5389 0.4427 0.079 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 Br1 0.0524(2) 0.0464(2) 0.03996(18) 0.02256(12) 0.00822(13) 0.00116(13) F1 0.0424(9) 0.0293(8) 0.0378(8) -0.0015(6) 0.0200(7) 0.0049(6) F2 0.0267(8) 0.0381(8) 0.0388(8) 0.0098(6) -0.0033(6) 0.0041(6) N1 0.0408(12) 0.0213(10) 0.0229(10) 0.0005(8) 0.0099(9) -0.0017(9) O1 0.0260(9) 0.0262(8) 0.0278(9) 0.0017(7) -0.0016(7) -0.0024(7) O2 0.0735(15) 0.0386(10) 0.0214(9) -0.0059(8) 0.0068(9) -0.0113(9) O3 0.0444(11) 0.0472(11) 0.0331(10) -0.0013(8) -0.0048(8) -0.0215(9) O4 0.0349(9) 0.0195(8) 0.0173(7) -0.0005(6) 0.0054(7) -0.0022(7) O5 0.0502(11) 0.0215(8) 0.0248(9) -0.0036(7) 0.0122(8) 0.0018(7) C1 0.0285(12) 0.0238(12) 0.0279(12) 0.0017(10) 0.0054(10) 0.0041(10) C2 0.0296(12) 0.0209(11) 0.0172(11) 0.0012(9) 0.0039(9) -0.0010(9) C3 0.0268(13) 0.0262(12) 0.0227(12) 0.0004(9) 0.0030(10) 0.0035(9) C4 0.0310(13) 0.0210(12) 0.0270(12) 0.0036(9) 0.0008(10) 0.0008(10) C5 0.0297(13) 0.0352(14) 0.0271(12) 0.0098(10) 0.0068(10) -0.0012(11) C6 0.0330(14) 0.0359(14) 0.0290(13) 0.0020(10) 0.0131(11) 0.0014(11) C7 0.0409(15) 0.0238(12) 0.0257(13) 0.0010(10) 0.0010(11) -0.0069(10) C8 0.060(3) 0.069(3) 0.0522(18) -0.011(2) 0.002(2) -0.039(2) C9 0.060(3) 0.069(3) 0.0522(18) -0.011(2) 0.002(2) -0.039(2) C8' 0.060(3) 0.069(3) 0.0522(18) -0.011(2) 0.002(2) -0.039(2) C9' 0.060(3) 0.069(3) 0.0522(18) -0.011(2) 0.002(2) -0.039(2) C10 0.0298(13) 0.0205(11) 0.0253(12) 0.0001(10) 0.0028(10) -0.0031(10) C11 0.0542(17) 0.0305(13) 0.0238(12) -0.0022(10) 0.0161(12) -0.0041(12) C12 0.061(2) 0.0439(17) 0.065(2) -0.0012(15) 0.0357(17) 0.0039(14) C13 0.0526(17) 0.0262(13) 0.0369(15) 0.0046(11) 0.0145(13) -0.0033(12) C14 0.056(2) 0.0475(18) 0.0543(19) 0.0122(15) 0.0131(15) 0.0036(15) _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 Br1 C5 1.871(2) . ? F1 C3 1.356(3) . ? F2 C3 1.362(3) . ? N1 C10 1.330(3) . ? N1 C11 1.465(3) . ? N1 C13 1.466(3) . ? O1 C4 1.433(3) . ? O1 C1 1.446(3) . ? O2 C7 1.195(3) . ? O3 C7 1.317(3) . ? O3 C8' 1.438(8) . ? O3 C8 1.548(16) . ? O4 C10 1.368(3) . ? O4 C2 1.422(2) . ? O5 C10 1.217(3) . ? C1 C6 1.513(3) . ? C1 C2 1.549(3) . ? C2 C7 1.528(3) . ? C2 C3 1.560(3) . ? C3 C4 1.527(3) . ? C4 C5 1.513(3) . ? C5 C6 1.310(4) . ? C8 C9 1.151(17) . ? C8' C9' 1.369(9) . ? C11 C12 1.503(4) . ? C13 C14 1.495(4) . ? 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 C10 N1 C11 122.90(19) . . ? C10 N1 C13 117.93(19) . . ? C11 N1 C13 118.84(18) . . ? C4 O1 C1 96.90(16) . . ? C7 O3 C8' 120.4(4) . . ? C7 O3 C8 106.4(6) . . ? C8' O3 C8 20.8(7) . . ? C10 O4 C2 116.05(16) . . ? O1 C1 C6 102.13(18) . . ? O1 C1 C2 99.43(17) . . ? C6 C1 C2 108.43(18) . . ? O4 C2 C7 112.42(18) . . ? O4 C2 C1 110.71(17) . . ? C7 C2 C1 115.73(19) . . ? O4 C2 C3 105.79(16) . . ? C7 C2 C3 111.95(18) . . ? C1 C2 C3 99.07(17) . . ? F1 C3 F2 105.45(18) . . ? F1 C3 C4 111.46(18) . . ? F2 C3 C4 112.75(18) . . ? F1 C3 C2 111.91(17) . . ? F2 C3 C2 112.30(18) . . ? C4 C3 C2 103.17(17) . . ? O1 C4 C5 101.04(18) . . ? O1 C4 C3 99.75(17) . . ? C5 C4 C3 105.07(18) . . ? C6 C5 C4 107.5(2) . . ? C6 C5 Br1 129.54(19) . . ? C4 C5 Br1 122.56(17) . . ? C5 C6 C1 105.0(2) . . ? O2 C7 O3 126.2(2) . . ? O2 C7 C2 124.1(2) . . ? O3 C7 C2 109.6(2) . . ? C9 C8 O3 118.1(13) . . ? C9' C8' O3 114.0(6) . . ? O5 C10 N1 126.8(2) . . ? O5 C10 O4 122.5(2) . . ? N1 C10 O4 110.70(19) . . ? N1 C11 C12 112.9(2) . . ? N1 C13 C14 113.3(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.536 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.064 data_9 _database_code_depnum_ccdc_archive 'CCDC 229971' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H18 Br2 F4 O12' _chemical_formula_weight 686.16 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' Br Br -0.2901 2.4595 '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 7.0091(8) _cell_length_b 11.5134(13) _cell_length_c 14.9095(17) _cell_angle_alpha 90.00 _cell_angle_beta 94.404(2) _cell_angle_gamma 90.00 _cell_volume 1199.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5017 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.18 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 3.474 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.444 _exptl_absorpt_correction_T_max 0.716 _exptl_absorpt_process_details ; absorption correction based on 6846 reflections (SADABS); Rint 0.077 before correction and 0.039 after. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8057 _diffrn_reflns_av_R_equivalents 0.0236 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4055 _reflns_number_gt 3792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _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^)+(0.0458P)^2^+0.0000P] 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 mixed _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 0.328(8) _refine_ls_number_reflns 4055 _refine_ls_number_parameters 348 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0708 _refine_ls_wR_factor_gt 0.0702 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.001 _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 Br1 Br 0.43742(5) 0.25852(3) -0.01801(3) 0.04071(14) Uani 1 1 d . . . F1 F 0.2784(3) 0.4169(2) 0.23759(15) 0.0316(5) Uani 1 1 d . . . F2 F 0.4023(3) 0.2840(2) 0.32717(14) 0.0375(6) Uani 1 1 d . . . O1 O 0.5596(4) 0.6002(2) 0.19575(17) 0.0292(6) Uani 1 1 d . . . O2 O 0.4563(4) 0.6979(3) 0.31239(19) 0.0341(7) Uani 1 1 d . . . O3 O 0.5543(3) 0.5141(3) 0.32855(15) 0.0237(5) Uani 1 1 d . . . O4 O 0.5595(4) 0.1722(2) 0.1910(2) 0.0360(7) Uani 1 1 d . . . H4 H 0.5051 0.1220 0.2211 0.054 Uiso 1 1 calc R . . O5 O 0.8861(4) 0.3116(3) 0.26412(19) 0.0291(7) Uani 1 1 d . . . O6 O 0.7955(4) 0.3670(3) 0.39847(18) 0.0406(8) Uani 1 1 d . . . C2 C 0.5186(6) 0.6125(4) 0.2812(3) 0.0271(9) Uani 1 1 d . . . C4 C 0.4308(6) 0.3461(4) 0.2526(3) 0.0279(9) Uani 1 1 d . . . C5 C 0.4353(5) 0.2648(4) 0.1720(2) 0.0288(8) Uani 1 1 d . . . H5 H 0.3036 0.2336 0.1571 0.035 Uiso 1 1 calc R . . C6 C 0.4943(5) 0.3320(4) 0.0938(3) 0.0264(9) Uani 1 1 d . . . C7 C 0.5819(5) 0.4330(4) 0.0979(2) 0.0264(9) Uani 1 1 d . . . H7 H 0.6029 0.4720 0.0434 0.032 Uiso 1 1 calc R . . C8 C 0.7801(6) 0.3590(4) 0.3111(3) 0.0265(9) Uani 1 1 d . . . C9 C 0.9670(8) 0.3105(5) 0.4465(3) 0.0644(18) Uani 1 1 d . . . H9A H 1.0721 0.3033 0.4061 0.077 Uiso 1 1 calc R . . H9B H 1.0132 0.3565 0.4999 0.077 Uiso 1 1 calc R . . C10 C 0.9023(10) 0.1958(6) 0.4734(4) 0.079(2) Uani 1 1 d . . . H10A H 0.7913 0.2043 0.5090 0.119 Uiso 1 1 calc R . . H10B H 1.0059 0.1567 0.5096 0.119 Uiso 1 1 calc R . . H10C H 0.8665 0.1494 0.4196 0.119 Uiso 1 1 calc R . . C3A C 0.6058(5) 0.4240(3) 0.2704(2) 0.0231(9) Uani 1 1 d . . . C7A C 0.6485(5) 0.4881(3) 0.1838(2) 0.0230(9) Uani 1 1 d . . . H7A H 0.7900 0.4998 0.1844 0.028 Uiso 1 1 calc R . . Br2 Br -0.05985(5) 1.02036(3) -0.03291(3) 0.03741(13) Uani 1 1 d . . . F1A F -0.2351(3) 0.8650(2) 0.21993(15) 0.0325(6) Uani 1 1 d . . . F2A F -0.1369(3) 1.0055(2) 0.30859(14) 0.0372(6) Uani 1 1 d . . . O1A O 0.0688(4) 0.6924(2) 0.19350(17) 0.0285(6) Uani 1 1 d . . . O2A O -0.0357(4) 0.5973(3) 0.30976(19) 0.0367(7) Uani 1 1 d . . . O3A O 0.0443(4) 0.7839(2) 0.32220(15) 0.0250(6) Uani 1 1 d . . . O4A O 0.0267(4) 1.1197(3) 0.1753(2) 0.0362(7) Uani 1 1 d . . . H4A H -0.0447 1.1760 0.1857 0.054 Uiso 1 1 calc R . . O5A O 0.3713(4) 0.9873(2) 0.25819(19) 0.0315(7) Uani 1 1 d . . . O6A O 0.2445(4) 0.9585(3) 0.38987(18) 0.0352(7) Uani 1 1 d . . . C2A C 0.0214(6) 0.6832(4) 0.2772(3) 0.0272(9) Uani 1 1 d . . . C4A C -0.0910(5) 0.9429(4) 0.2368(2) 0.0264(9) Uani 1 1 d . . . C5A C -0.0860(5) 1.0203(4) 0.1555(2) 0.0276(8) Uani 1 1 d . . . H5A H -0.2194 1.0452 0.1360 0.033 Uiso 1 1 calc R . . C6A C -0.0075(5) 0.9533(4) 0.0816(2) 0.0254(9) Uani 1 1 d . . . C7A' C 0.0866(5) 0.8553(4) 0.0908(2) 0.0245(9) Uani 1 1 d . . . H7A' H 0.1148 0.8140 0.0382 0.029 Uiso 1 1 calc R . . C8A C 0.2551(5) 0.9468(4) 0.3035(2) 0.0253(9) Uani 1 1 d . . . C9A C 0.4045(6) 1.0151(5) 0.4399(3) 0.0443(11) Uani 1 1 d . . . H9A1 H 0.3600 1.0493 0.4955 0.053 Uiso 1 1 calc R . . H9A2 H 0.4515 1.0792 0.4032 0.053 Uiso 1 1 calc R . . C10A C 0.5621(6) 0.9351(5) 0.4638(3) 0.0489(12) Uani 1 1 d . . . H10D H 0.5142 0.8684 0.4961 0.073 Uiso 1 1 calc R . . H10E H 0.6608 0.9751 0.5023 0.073 Uiso 1 1 calc R . . H10F H 0.6170 0.9083 0.4089 0.073 Uiso 1 1 calc R . . C3B C 0.0906(5) 0.8727(3) 0.2612(2) 0.0220(9) Uani 1 1 d . . . C7B C 0.1510(6) 0.8060(3) 0.1800(2) 0.0224(9) Uani 1 1 d . . . H7B H 0.2936 0.7991 0.1845 0.027 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 Br1 0.0407(3) 0.0474(3) 0.0337(2) -0.0166(2) 0.00087(16) -0.0075(2) F1 0.0241(12) 0.0343(14) 0.0371(13) -0.0037(11) 0.0062(9) 0.0001(11) F2 0.0477(13) 0.0321(14) 0.0351(13) 0.0076(11) 0.0184(10) -0.0072(11) O1 0.0451(18) 0.0192(15) 0.0232(15) 0.0004(12) 0.0013(11) 0.0022(13) O2 0.0461(18) 0.0241(16) 0.0319(17) -0.0041(13) 0.0013(13) 0.0082(14) O3 0.0290(13) 0.0238(14) 0.0190(12) -0.0007(13) 0.0060(10) 0.0040(13) O4 0.0393(16) 0.0167(14) 0.054(2) 0.0024(13) 0.0179(14) -0.0009(13) O5 0.0265(14) 0.0314(17) 0.0300(15) -0.0062(12) 0.0063(12) 0.0012(12) O6 0.0421(16) 0.057(2) 0.0227(15) 0.0091(14) 0.0048(12) 0.0241(15) C2 0.032(2) 0.025(2) 0.023(2) 0.0033(18) -0.0064(16) 0.000(2) C4 0.029(2) 0.026(2) 0.031(2) 0.0032(17) 0.0144(16) 0.0047(18) C5 0.0262(19) 0.028(2) 0.033(2) -0.005(2) 0.0071(15) -0.0082(19) C6 0.022(2) 0.031(2) 0.027(2) -0.0062(17) 0.0050(15) 0.0017(18) C7 0.025(2) 0.036(3) 0.0186(19) 0.0029(17) 0.0036(15) 0.0019(19) C8 0.030(2) 0.022(2) 0.028(2) 0.0023(17) 0.0056(17) -0.0006(17) C9 0.072(4) 0.089(5) 0.033(3) 0.011(3) 0.009(2) 0.046(3) C10 0.119(5) 0.064(4) 0.051(4) -0.009(3) -0.020(4) 0.023(4) C3A 0.025(2) 0.023(2) 0.021(2) 0.0008(16) 0.0039(15) 0.0005(17) C7A 0.030(2) 0.018(2) 0.0207(19) -0.0002(15) 0.0046(15) 0.0004(16) Br2 0.0366(2) 0.0486(3) 0.0272(2) 0.0130(2) 0.00345(16) 0.0089(2) F1A 0.0219(11) 0.0408(15) 0.0352(13) 0.0033(11) 0.0049(9) -0.0068(11) F2A 0.0454(13) 0.0381(14) 0.0302(12) -0.0079(12) 0.0171(10) 0.0050(11) O1A 0.0399(17) 0.0261(16) 0.0189(15) -0.0034(12) -0.0008(11) -0.0027(13) O2A 0.0498(19) 0.0288(17) 0.0306(16) 0.0034(14) -0.0030(13) -0.0164(14) O3A 0.0343(14) 0.0238(16) 0.0171(12) -0.0012(11) 0.0033(10) -0.0081(13) O4A 0.0453(17) 0.0225(16) 0.0429(18) -0.0003(13) 0.0169(13) 0.0039(13) O5A 0.0322(15) 0.0284(18) 0.0343(16) 0.0082(13) 0.0054(13) -0.0098(13) O6A 0.0437(16) 0.0384(16) 0.0234(15) -0.0042(12) 0.0019(12) -0.0171(14) C2A 0.029(2) 0.028(2) 0.024(2) 0.0014(18) -0.0036(17) -0.003(2) C4A 0.027(2) 0.032(2) 0.021(2) -0.0065(16) 0.0099(15) 0.0044(18) C5A 0.0266(18) 0.029(2) 0.0276(19) 0.002(2) 0.0065(15) -0.001(2) C6A 0.0239(19) 0.032(2) 0.0206(19) 0.0051(16) 0.0048(15) 0.0017(18) C7A' 0.030(2) 0.024(2) 0.021(2) -0.0041(16) 0.0056(15) 0.0006(18) C8A 0.031(2) 0.021(2) 0.024(2) 0.0026(15) 0.0020(16) 0.0018(17) C9A 0.059(3) 0.042(3) 0.030(2) -0.011(2) -0.0048(19) -0.027(3) C10A 0.049(3) 0.060(3) 0.037(3) 0.007(2) 0.000(2) -0.009(2) C3B 0.028(2) 0.022(2) 0.0174(19) 0.0037(15) 0.0076(15) -0.0060(17) C7B 0.028(2) 0.022(2) 0.0182(19) -0.0012(15) 0.0040(15) -0.0006(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 Br1 C6 1.884(4) . ? F1 C4 1.349(5) . ? F2 C4 1.349(4) . ? O1 C2 1.336(5) . ? O1 C7A 1.451(5) . ? O2 C2 1.185(5) . ? O3 C2 1.348(5) . ? O3 C3A 1.416(5) . ? O4 C5 1.392(5) . ? O5 C8 1.191(5) . ? O6 C8 1.303(5) . ? O6 C9 1.500(5) . ? C4 C5 1.526(6) . ? C4 C3A 1.526(6) . ? C5 C6 1.484(5) . ? C6 C7 1.315(6) . ? C7 C7A 1.473(5) . ? C8 C3A 1.519(5) . ? C9 C10 1.462(9) . ? C3A C7A 1.536(5) . ? Br2 C6A 1.884(4) . ? F1A C4A 1.359(5) . ? F2A C4A 1.350(4) . ? O1A C2A 1.320(5) . ? O1A C7B 1.450(5) . ? O2A C2A 1.184(5) . ? O3A C2A 1.343(5) . ? O3A C3B 1.423(4) . ? O4A C5A 1.409(5) . ? O5A C8A 1.193(4) . ? O6A C8A 1.302(4) . ? O6A C9A 1.453(5) . ? C4A C5A 1.506(6) . ? C4A C3B 1.528(6) . ? C5A C6A 1.484(5) . ? C6A C7A' 1.310(5) . ? C7A' C7B 1.485(5) . ? C8A C3B 1.530(5) . ? C9A C10A 1.461(7) . ? C3B C7B 1.521(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C7A 109.7(3) . . ? C2 O3 C3A 109.9(3) . . ? C8 O6 C9 116.7(3) . . ? O2 C2 O1 125.1(4) . . ? O2 C2 O3 123.5(4) . . ? O1 C2 O3 111.4(4) . . ? F1 C4 F2 107.0(3) . . ? F1 C4 C5 107.7(3) . . ? F2 C4 C5 109.7(3) . . ? F1 C4 C3A 106.8(3) . . ? F2 C4 C3A 109.7(3) . . ? C5 C4 C3A 115.6(3) . . ? O4 C5 C6 110.6(3) . . ? O4 C5 C4 111.1(3) . . ? C6 C5 C4 108.9(4) . . ? C7 C6 C5 125.6(4) . . ? C7 C6 Br1 120.3(3) . . ? C5 C6 Br1 114.1(3) . . ? C6 C7 C7A 122.5(4) . . ? O5 C8 O6 127.8(4) . . ? O5 C8 C3A 120.7(4) . . ? O6 C8 C3A 111.5(3) . . ? C10 C9 O6 105.6(5) . . ? O3 C3A C8 110.6(3) . . ? O3 C3A C4 107.3(3) . . ? C8 C3A C4 113.0(3) . . ? O3 C3A C7A 103.8(3) . . ? C8 C3A C7A 111.7(3) . . ? C4 C3A C7A 110.0(3) . . ? O1 C7A C7 112.3(3) . . ? O1 C7A C3A 102.2(3) . . ? C7 C7A C3A 117.1(3) . . ? C2A O1A C7B 109.6(3) . . ? C2A O3A C3B 109.0(3) . . ? C8A O6A C9A 117.0(3) . . ? O2A C2A O1A 124.9(4) . . ? O2A C2A O3A 123.2(4) . . ? O1A C2A O3A 111.9(4) . . ? F2A C4A F1A 106.2(3) . . ? F2A C4A C5A 110.1(4) . . ? F1A C4A C5A 107.7(3) . . ? F2A C4A C3B 109.8(3) . . ? F1A C4A C3B 106.8(3) . . ? C5A C4A C3B 115.7(3) . . ? O4A C5A C6A 110.1(3) . . ? O4A C5A C4A 111.1(3) . . ? C6A C5A C4A 108.8(4) . . ? C7A' C6A C5A 125.7(4) . . ? C7A' C6A Br2 120.6(3) . . ? C5A C6A Br2 113.8(3) . . ? C6A C7A' C7B 122.6(3) . . ? O5A C8A O6A 127.8(4) . . ? O5A C8A C3B 120.7(3) . . ? O6A C8A C3B 111.5(3) . . ? O6A C9A C10A 112.4(4) . . ? O3A C3B C7B 103.7(3) . . ? O3A C3B C4A 107.8(3) . . ? C7B C3B C4A 110.8(3) . . ? O3A C3B C8A 109.8(3) . . ? C7B C3B C8A 111.3(3) . . ? C4A C3B C8A 113.0(3) . . ? O1A C7B C7A' 111.9(3) . . ? O1A C7B C3B 102.0(3) . . ? C7A' C7B C3B 115.9(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.474 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.068