# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email harned@umn.edu _publ_contact_author_name 'Andrew Harned' loop_ _publ_author_name 'Rodolfo Tello-Aburto' 'Kyle Kalstabakken' 'Kelly Volp' 'Andrew Harned' data_10200b _database_code_depnum_ccdc_archive 'CCDC 837018' #TrackingRef '- Compound_12r.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 10200 _chemical_melting_point ? _chemical_formula_moiety 'C16 H19 Br O5' _chemical_formula_sum 'C16 H19 Br O5' _chemical_formula_weight 371.22 _chemical_absolute_configuration rmad 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 11.6427(3) _cell_length_b 11.6427(3) _cell_length_c 24.4087(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3308.66(19) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7748 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 2.505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3673 _exptl_absorpt_correction_T_max 0.4341 _exptl_absorpt_process_details 'SADABS, R. Blessing, 1995' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Platform CCD' _diffrn_measurement_method 'area detector, omega scans per phi' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3803 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0133 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3803 _reflns_number_gt 3647 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Bruker' _computing_cell_refinement 'SAINT, Bruker' _computing_data_reduction 'SAINT, Bruker' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL, Bruker' _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^)+(0.0551P)^2^+0.9981P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.004(7) _refine_ls_number_reflns 3803 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0288 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0754 _refine_ls_wR_factor_gt 0.0741 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.68875(2) 0.39815(2) 0.082480(10) 0.03420(8) Uani 1 1 d . . . O1 O 0.43330(15) 0.35029(16) 0.06102(7) 0.0373(4) Uani 1 1 d . . . O2 O 0.55604(13) 0.02311(13) 0.06039(6) 0.0236(3) Uani 1 1 d . . . O3 O 0.37842(14) -0.00575(14) 0.09155(6) 0.0296(3) Uani 1 1 d . . . O4 O 0.26281(14) -0.05825(13) -0.01617(6) 0.0262(3) Uani 1 1 d . . . O5 O 0.27581(12) 0.10210(13) -0.06857(6) 0.0234(3) Uani 1 1 d . . . C1 C 0.49331(19) 0.28065(18) 0.03786(8) 0.0226(4) Uani 1 1 d . . . C2 C 0.61869(18) 0.27092(17) 0.04847(8) 0.0231(4) Uani 1 1 d . . . C3 C 0.67771(18) 0.17740(19) 0.03528(8) 0.0250(4) Uani 1 1 d . . . H3A H 0.7586 0.1755 0.0402 0.030 Uiso 1 1 calc R . . C4 C 0.61503(18) 0.07308(17) 0.01221(8) 0.0221(4) Uani 1 1 d . . . C5 C 0.51907(16) 0.10746(17) -0.02712(7) 0.0196(4) Uani 1 1 d . . . H5A H 0.5270 0.0928 -0.0673 0.024 Uiso 1 1 calc R . . C6 C 0.44808(17) 0.20482(16) -0.00701(8) 0.0196(4) Uani 1 1 d . . . H6A H 0.4054 0.2467 -0.0364 0.023 Uiso 1 1 calc R . . C7 C 0.40774(16) 0.08026(16) 0.00206(7) 0.0178(4) Uani 1 1 d . . . C8 C 0.43986(18) 0.02752(17) 0.05580(8) 0.0207(4) Uani 1 1 d . . . C9 C 0.30521(16) 0.03270(16) -0.02797(7) 0.0186(3) Uani 1 1 d . . . C10 C 0.18684(19) 0.06876(19) -0.10959(8) 0.0250(4) Uani 1 1 d . . . C11 C 0.1897(3) 0.1689(2) -0.14899(10) 0.0379(5) Uani 1 1 d . . . H11A H 0.2657 0.1735 -0.1661 0.057 Uiso 1 1 calc R . . H11B H 0.1741 0.2403 -0.1290 0.057 Uiso 1 1 calc R . . H11C H 0.1312 0.1579 -0.1774 0.057 Uiso 1 1 calc R . . C12 C 0.07062(18) 0.0596(2) -0.08180(10) 0.0326(5) Uani 1 1 d . . . H12A H 0.0715 -0.0048 -0.0559 0.049 Uiso 1 1 calc R . . H12B H 0.0111 0.0465 -0.1095 0.049 Uiso 1 1 calc R . . H12C H 0.0543 0.1310 -0.0620 0.049 Uiso 1 1 calc R . . C13 C 0.2220(2) -0.0411(2) -0.13821(9) 0.0295(5) Uani 1 1 d . . . H13A H 0.2159 -0.1056 -0.1126 0.044 Uiso 1 1 calc R . . H13B H 0.3016 -0.0343 -0.1509 0.044 Uiso 1 1 calc R . . H13C H 0.1714 -0.0546 -0.1696 0.044 Uiso 1 1 calc R . . C14 C 0.69723(19) -0.01915(19) -0.00930(10) 0.0302(5) Uani 1 1 d . . . H14A H 0.7478 -0.0438 0.0216 0.036 Uiso 1 1 calc R . . C15 C 0.6325(2) -0.1249(2) -0.03024(11) 0.0370(5) Uani 1 1 d . . . H15A H 0.6876 -0.1857 -0.0393 0.056 Uiso 1 1 calc R . . H15B H 0.5887 -0.1044 -0.0631 0.056 Uiso 1 1 calc R . . H15C H 0.5799 -0.1524 -0.0018 0.056 Uiso 1 1 calc R . . C16 C 0.7735(2) 0.0313(2) -0.05425(12) 0.0421(6) Uani 1 1 d . . . H16A H 0.8169 0.0965 -0.0395 0.063 Uiso 1 1 calc R . . H16B H 0.7254 0.0575 -0.0848 0.063 Uiso 1 1 calc R . . H16C H 0.8270 -0.0276 -0.0673 0.063 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 0.02703(12) 0.02871(12) 0.04688(14) -0.01460(10) 0.00190(9) -0.00671(9) O1 0.0302(9) 0.0408(10) 0.0410(9) -0.0180(8) -0.0073(7) 0.0124(7) O2 0.0218(7) 0.0253(7) 0.0237(7) 0.0042(6) -0.0046(6) 0.0008(6) O3 0.0311(8) 0.0365(8) 0.0211(6) 0.0070(6) 0.0026(6) -0.0064(7) O4 0.0267(7) 0.0252(7) 0.0267(7) 0.0035(6) -0.0039(6) -0.0068(6) O5 0.0226(7) 0.0239(7) 0.0236(6) 0.0043(6) -0.0059(5) -0.0028(6) C1 0.0241(10) 0.0220(10) 0.0218(9) -0.0005(7) -0.0012(8) 0.0011(8) C2 0.0241(10) 0.0207(9) 0.0246(9) -0.0035(7) -0.0003(8) -0.0069(8) C3 0.0184(9) 0.0277(10) 0.0290(10) -0.0058(8) -0.0004(8) -0.0037(8) C4 0.0189(9) 0.0215(9) 0.0259(9) -0.0035(7) 0.0022(7) -0.0009(7) C5 0.0196(9) 0.0212(9) 0.0182(8) 0.0003(7) 0.0031(7) -0.0042(8) C6 0.0212(9) 0.0178(9) 0.0197(8) 0.0017(7) -0.0011(7) -0.0023(7) C7 0.0179(8) 0.0183(9) 0.0172(7) 0.0028(6) 0.0008(7) -0.0018(7) C8 0.0229(9) 0.0201(9) 0.0191(8) 0.0007(7) -0.0035(7) 0.0000(7) C9 0.0166(8) 0.0211(9) 0.0179(8) -0.0007(7) 0.0010(7) 0.0007(7) C10 0.0213(9) 0.0322(10) 0.0216(9) -0.0012(8) -0.0063(8) 0.0010(8) C11 0.0428(14) 0.0393(13) 0.0317(11) 0.0094(10) -0.0119(11) 0.0045(11) C12 0.0184(10) 0.0481(14) 0.0315(11) -0.0102(10) -0.0026(8) 0.0032(9) C13 0.0281(11) 0.0370(12) 0.0235(10) -0.0046(8) 0.0011(8) 0.0001(9) C14 0.0226(10) 0.0264(10) 0.0417(12) -0.0084(9) 0.0015(9) 0.0025(9) C15 0.0341(12) 0.0267(12) 0.0503(14) -0.0098(10) 0.0041(10) -0.0014(9) C16 0.0338(13) 0.0409(14) 0.0515(15) -0.0109(11) 0.0159(11) -0.0027(11) _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 C2 1.8838(19) . ? O1 C1 1.210(3) . ? O2 C8 1.358(2) . ? O2 C4 1.481(2) . ? O3 C8 1.193(3) . ? O4 C9 1.203(2) . ? O5 C9 1.324(2) . ? O5 C10 1.492(2) . ? C1 C2 1.487(3) . ? C1 C6 1.502(3) . ? C2 C3 1.327(3) . ? C3 C4 1.525(3) . ? C3 H3A 0.9500 . ? C4 C5 1.526(3) . ? C4 C14 1.531(3) . ? C5 C6 1.486(3) . ? C5 C7 1.513(2) . ? C5 H5A 1.0000 . ? C6 C7 1.540(3) . ? C6 H6A 1.0000 . ? C7 C8 1.496(3) . ? C7 C9 1.506(3) . ? C10 C11 1.512(3) . ? C10 C13 1.514(3) . ? C10 C12 1.517(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.532(3) . ? C14 C16 1.529(3) . ? C14 H14A 1.0000 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 C8 O2 C4 112.43(15) . . ? C9 O5 C10 121.55(16) . . ? O1 C1 C2 122.44(19) . . ? O1 C1 C6 122.13(19) . . ? C2 C1 C6 115.24(17) . . ? C3 C2 C1 121.91(18) . . ? C3 C2 Br1 121.86(16) . . ? C1 C2 Br1 116.23(15) . . ? C2 C3 C4 119.69(18) . . ? C2 C3 H3A 120.2 . . ? C4 C3 H3A 120.2 . . ? O2 C4 C3 103.97(15) . . ? O2 C4 C5 105.25(15) . . ? C3 C4 C5 111.95(17) . . ? O2 C4 C14 106.66(16) . . ? C3 C4 C14 112.72(18) . . ? C5 C4 C14 115.20(16) . . ? C6 C5 C7 61.81(13) . . ? C6 C5 C4 113.53(15) . . ? C7 C5 C4 106.03(15) . . ? C6 C5 H5A 120.3 . . ? C7 C5 H5A 120.3 . . ? C4 C5 H5A 120.3 . . ? C5 C6 C1 119.62(17) . . ? C5 C6 C7 59.93(12) . . ? C1 C6 C7 123.74(16) . . ? C5 C6 H6A 114.3 . . ? C1 C6 H6A 114.3 . . ? C7 C6 H6A 114.3 . . ? C8 C7 C9 118.29(16) . . ? C8 C7 C5 106.54(16) . . ? C9 C7 C5 121.79(15) . . ? C8 C7 C6 115.87(16) . . ? C9 C7 C6 121.18(16) . . ? C5 C7 C6 58.26(12) . . ? O3 C8 O2 121.63(18) . . ? O3 C8 C7 128.67(19) . . ? O2 C8 C7 109.68(17) . . ? O4 C9 O5 127.60(18) . . ? O4 C9 C7 122.15(17) . . ? O5 C9 C7 110.18(15) . . ? O5 C10 C11 102.17(17) . . ? O5 C10 C13 109.97(17) . . ? C11 C10 C13 110.63(18) . . ? O5 C10 C12 109.72(16) . . ? C11 C10 C12 111.0(2) . . ? C13 C10 C12 112.82(19) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C4 111.77(19) . . ? C15 C14 C16 110.8(2) . . ? C4 C14 C16 109.83(19) . . ? C15 C14 H14A 108.1 . . ? C4 C14 H14A 108.1 . . ? C16 C14 H14A 108.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 161.2(2) . . . . ? C6 C1 C2 C3 -23.7(3) . . . . ? O1 C1 C2 Br1 -18.1(3) . . . . ? C6 C1 C2 Br1 156.99(14) . . . . ? C1 C2 C3 C4 -4.3(3) . . . . ? Br1 C2 C3 C4 174.90(14) . . . . ? C8 O2 C4 C3 115.41(18) . . . . ? C8 O2 C4 C5 -2.4(2) . . . . ? C8 O2 C4 C14 -125.27(19) . . . . ? C2 C3 C4 O2 -74.2(2) . . . . ? C2 C3 C4 C5 38.9(3) . . . . ? C2 C3 C4 C14 170.72(19) . . . . ? O2 C4 C5 C6 68.40(19) . . . . ? C3 C4 C5 C6 -43.9(2) . . . . ? C14 C4 C5 C6 -174.43(17) . . . . ? O2 C4 C5 C7 2.67(19) . . . . ? C3 C4 C5 C7 -109.65(18) . . . . ? C14 C4 C5 C7 119.83(18) . . . . ? C7 C5 C6 C1 114.15(19) . . . . ? C4 C5 C6 C1 17.9(2) . . . . ? C4 C5 C6 C7 -96.22(17) . . . . ? O1 C1 C6 C5 -169.3(2) . . . . ? C2 C1 C6 C5 15.7(3) . . . . ? O1 C1 C6 C7 -97.5(3) . . . . ? C2 C1 C6 C7 87.4(2) . . . . ? C6 C5 C7 C8 -110.57(17) . . . . ? C4 C5 C7 C8 -2.1(2) . . . . ? C6 C5 C7 C9 109.44(19) . . . . ? C4 C5 C7 C9 -142.06(17) . . . . ? C4 C5 C7 C6 108.50(17) . . . . ? C5 C6 C7 C8 94.14(18) . . . . ? C1 C6 C7 C8 -13.3(3) . . . . ? C5 C6 C7 C9 -110.47(19) . . . . ? C1 C6 C7 C9 142.07(19) . . . . ? C1 C6 C7 C5 -107.5(2) . . . . ? C4 O2 C8 O3 -177.73(19) . . . . ? C4 O2 C8 C7 1.2(2) . . . . ? C9 C7 C8 O3 -38.9(3) . . . . ? C5 C7 C8 O3 179.4(2) . . . . ? C6 C7 C8 O3 117.2(2) . . . . ? C9 C7 C8 O2 142.28(17) . . . . ? C5 C7 C8 O2 0.6(2) . . . . ? C6 C7 C8 O2 -61.6(2) . . . . ? C10 O5 C9 O4 -5.2(3) . . . . ? C10 O5 C9 C7 171.90(16) . . . . ? C8 C7 C9 O4 -14.8(3) . . . . ? C5 C7 C9 O4 120.8(2) . . . . ? C6 C7 C9 O4 -169.62(18) . . . . ? C8 C7 C9 O5 167.95(17) . . . . ? C5 C7 C9 O5 -56.5(2) . . . . ? C6 C7 C9 O5 13.1(2) . . . . ? C9 O5 C10 C11 -175.97(19) . . . . ? C9 O5 C10 C13 -58.5(2) . . . . ? C9 O5 C10 C12 66.2(2) . . . . ? O2 C4 C14 C15 64.3(2) . . . . ? C3 C4 C14 C15 177.8(2) . . . . ? C5 C4 C14 C15 -52.0(3) . . . . ? O2 C4 C14 C16 -172.25(18) . . . . ? C3 C4 C14 C16 -58.8(2) . . . . ? C5 C4 C14 C16 71.4(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.485 _refine_diff_density_min -0.231 _refine_diff_density_rms 0.062