# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/435 data_u3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H33 Br O12' _chemical_formula_weight 569.39 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 'orthorhombic' _symmetry_space_group_name_H-M ' P 2(1) 2(1) 2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.952(2) _cell_length_b 13.551(2) _cell_length_c 17.076(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2765.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 1.542 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6548 _exptl_absorpt_correction_T_max 0.6991 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1879 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0687 _diffrn_reflns_limit_h_min -2 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 24.96 _reflns_number_total 1824 _reflns_number_gt 1189 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+3.3023P] 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 SHELXL _refine_ls_extinction_coef 0.0015(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 1824 _refine_ls_number_parameters 317 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1175 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.1438 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.346 _refine_ls_restrained_S_all 1.346 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.06688(18) 0.45159(14) 0.40570(12) 0.1379(9) Uani 1 d . . . C1 C 0.3099(19) 0.3643(13) 0.3581(11) 0.177(10) Uani 1 d . . . H1A H 0.3009 0.4346 0.3605 0.212 Uiso 1 calc R . . H1B H 0.2831 0.3406 0.3086 0.212 Uiso 1 calc R . . H1C H 0.3876 0.3479 0.3637 0.212 Uiso 1 calc R . . C2 C 0.2457(16) 0.3181(12) 0.4217(11) 0.115(6) Uani 1 d . . . O2 O 0.2421(13) 0.2312(9) 0.4322(9) 0.181(6) Uani 1 d . . . C3 C 0.1738(16) 0.3850(11) 0.4762(8) 0.099(5) Uani 1 d . . . C4 C 0.2430(15) 0.4628(12) 0.5110(8) 0.100(5) Uani 1 d . . . H4 H 0.2680 0.5082 0.4699 0.120 Uiso 1 calc R . . O1' O 0.1856(8) 0.5166(6) 0.5698(4) 0.077(3) Uani 1 d . . . O4 O 0.3391(12) 0.4150(8) 0.5457(7) 0.136(5) Uani 1 d . . . C5 C 0.1061(15) 0.3292(11) 0.5362(10) 0.137(7) Uani 1 d . . . H5A H 0.0626 0.2792 0.5105 0.164 Uiso 1 calc R . . H5B H 0.0571 0.3740 0.5630 0.164 Uiso 1 calc R . . H5C H 0.1556 0.2988 0.5733 0.164 Uiso 1 calc R . . C6 C 0.449(2) 0.4678(17) 0.5563(13) 0.177(10) Uani 1 d . . . H6A H 0.4357 0.5345 0.5746 0.213 Uiso 1 calc R . . H6B H 0.4880 0.4714 0.5066 0.213 Uiso 1 calc R . . C7 C 0.527(3) 0.407(4) 0.621(3) 0.36(3) Uani 1 d . . . H7A H 0.5203 0.3352 0.6190 0.430 Uiso 1 calc R . . H7B H 0.6041 0.4278 0.6247 0.430 Uiso 1 calc R . . C8 C 0.458(3) 0.450(3) 0.671(2) 0.32(3) Uani 1 d . . . H8A H 0.4771 0.4318 0.7238 0.383 Uiso 1 calc R . . H8B H 0.3822 0.4300 0.6605 0.383 Uiso 1 calc R . . H8C H 0.4636 0.5206 0.6657 0.383 Uiso 1 calc R . . C1' C 0.1737(12) 0.6181(9) 0.5589(8) 0.064(4) Uani 1 d . . . H1' H 0.1502 0.6349 0.5056 0.077 Uiso 1 calc R . . C2' C 0.0935(11) 0.6540(9) 0.6196(7) 0.068(4) Uani 1 d . . . H2' H 0.1159 0.6314 0.6718 0.081 Uiso 1 calc R . . O2' O -0.0167(7) 0.6166(6) 0.5996(5) 0.074(2) Uani 1 d . . . C3' C 0.0863(10) 0.7663(9) 0.6169(6) 0.057(3) Uani 1 d . . . H3' H 0.0504 0.7875 0.5681 0.069 Uiso 1 calc R . . O3' O 0.0211(7) 0.7977(6) 0.6828(5) 0.067(2) Uani 1 d . . . C4' C 0.2005(10) 0.8127(8) 0.6239(7) 0.056(3) Uani 1 d . . . H4' H 0.2293 0.8057 0.6774 0.067 Uiso 1 calc R . . O4' O 0.1888(7) 0.9134(6) 0.6042(5) 0.069(2) Uani 1 d . . . C5' C 0.2788(9) 0.7653(8) 0.5660(7) 0.053(3) Uani 1 d . . . H5' H 0.2523 0.7789 0.5128 0.064 Uiso 1 calc R . . O5' O 0.2782(7) 0.6608(6) 0.5792(5) 0.069(2) Uani 1 d . . . C6' C 0.4028(10) 0.7960(10) 0.5727(7) 0.084(4) Uani 1 d . . . H6A' H 0.4466 0.7637 0.5323 0.101 Uiso 1 calc R . . H6B' H 0.4102 0.8668 0.5663 0.101 Uiso 1 calc R . . O6' O 0.4417(8) 0.7669(7) 0.6486(5) 0.080(3) Uani 1 d . . . C7' C -0.0650(14) 0.5623(11) 0.6523(10) 0.093(5) Uani 1 d . . . C8' C -0.1769(12) 0.5235(12) 0.6196(9) 0.115(6) Uani 1 d . . . H8A' H -0.2143 0.4852 0.6591 0.138 Uiso 1 calc R . . H8B' H -0.1629 0.4828 0.5747 0.138 Uiso 1 calc R . . H8C' H -0.2233 0.5782 0.6048 0.138 Uiso 1 calc R . . O7' O -0.0403(8) 0.5532(9) 0.7181(6) 0.118(4) Uani 1 d . . . C9' C -0.0781(15) 0.8401(11) 0.6670(10) 0.094(5) Uani 1 d . . . C10' C -0.1402(12) 0.8642(11) 0.7395(9) 0.121(6) Uani 1 d . . . H10A H -0.2096 0.8955 0.7262 0.145 Uiso 1 calc R . . H10B H -0.0962 0.9080 0.7712 0.145 Uiso 1 calc R . . H10C H -0.1550 0.8046 0.7681 0.145 Uiso 1 calc R . . O9' O -0.1100(8) 0.8581(10) 0.6024(8) 0.138(5) Uani 1 d . . . C11' C 0.2397(15) 0.9815(9) 0.6488(10) 0.078(4) Uani 1 d . . . C12' C 0.2125(12) 1.0813(10) 0.6198(9) 0.108(6) Uani 1 d . . . H12A H 0.2507 1.1296 0.6511 0.129 Uiso 1 calc R . . H12B H 0.1332 1.0918 0.6233 0.129 Uiso 1 calc R . . H12C H 0.2358 1.0873 0.5662 0.129 Uiso 1 calc R . . O11' O 0.3008(9) 0.9640(8) 0.7023(6) 0.107(4) Uani 1 d . . . C13' C 0.5438(16) 0.7305(11) 0.6501(10) 0.093(5) Uani 1 d . . . C14' C 0.5748(12) 0.6980(11) 0.7299(9) 0.122(6) Uani 1 d . . . H14A H 0.6486 0.6700 0.7290 0.147 Uiso 1 calc R . . H14B H 0.5223 0.6493 0.7478 0.147 Uiso 1 calc R . . H14C H 0.5737 0.7536 0.7648 0.147 Uiso 1 calc R . . O13' O 0.5974(9) 0.7194(11) 0.5939(9) 0.154(6) Uani 1 d . . . 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 0.1532(17) 0.1296(15) 0.1311(15) -0.0424(13) -0.0397(14) 0.0112(15) C1 0.23(2) 0.151(18) 0.155(17) -0.047(14) 0.119(18) -0.029(18) C2 0.147(16) 0.066(11) 0.133(16) -0.020(12) 0.008(13) 0.007(12) O2 0.244(16) 0.077(8) 0.221(15) -0.045(10) 0.033(13) 0.020(10) C3 0.137(14) 0.085(10) 0.076(10) -0.032(10) -0.007(11) 0.022(12) C4 0.135(14) 0.103(12) 0.063(9) -0.028(10) 0.008(10) -0.003(13) O1' 0.106(7) 0.067(6) 0.059(6) -0.003(4) 0.003(5) -0.003(5) O4 0.123(10) 0.104(9) 0.181(12) -0.003(8) -0.013(10) 0.046(9) C5 0.18(2) 0.074(11) 0.159(15) 0.002(11) 0.060(15) -0.013(12) C6 0.14(2) 0.19(2) 0.20(2) -0.044(18) 0.062(17) -0.08(2) C7 0.11(2) 0.46(8) 0.50(7) -0.09(6) -0.05(3) 0.09(3) C8 0.26(4) 0.25(4) 0.46(7) 0.08(4) -0.24(5) -0.05(4) C1' 0.071(10) 0.041(8) 0.080(9) 0.016(7) -0.016(9) -0.012(8) C2' 0.075(11) 0.061(9) 0.068(9) 0.008(7) -0.006(8) -0.011(8) O2' 0.079(6) 0.073(5) 0.069(5) 0.015(6) -0.004(5) -0.015(5) C3' 0.048(8) 0.084(10) 0.040(7) 0.002(6) 0.001(7) -0.003(8) O3' 0.061(6) 0.073(6) 0.068(6) -0.003(5) -0.009(5) 0.008(5) C4' 0.060(9) 0.062(9) 0.045(7) 0.000(6) -0.009(7) 0.004(7) O4' 0.085(6) 0.044(5) 0.077(6) -0.002(5) 0.004(5) -0.012(5) C5' 0.053(8) 0.056(8) 0.051(7) -0.004(6) -0.008(6) -0.006(7) O5' 0.061(6) 0.060(5) 0.087(6) -0.007(5) -0.007(5) 0.005(5) C6' 0.057(9) 0.115(11) 0.079(10) 0.020(9) 0.010(8) 0.006(9) O6' 0.044(5) 0.124(8) 0.072(6) -0.002(5) -0.002(5) 0.008(6) C7' 0.090(12) 0.092(11) 0.096(11) 0.037(10) 0.001(12) -0.016(11) C8' 0.074(10) 0.142(14) 0.130(13) 0.041(11) 0.006(10) -0.017(11) O7' 0.094(8) 0.169(10) 0.092(7) 0.055(8) -0.004(6) -0.010(8) C9' 0.089(13) 0.099(12) 0.093(13) -0.007(10) -0.008(12) 0.013(11) C10' 0.104(12) 0.127(14) 0.131(14) -0.040(12) 0.053(12) -0.038(12) O9' 0.070(7) 0.211(13) 0.133(10) -0.002(11) -0.014(8) 0.057(8) C11' 0.107(13) 0.032(9) 0.095(11) -0.007(9) 0.023(10) 0.005(9) C12' 0.079(11) 0.098(13) 0.146(15) -0.009(11) -0.011(11) -0.012(9) O11' 0.114(8) 0.105(8) 0.102(7) -0.009(7) -0.046(7) 0.005(8) C13' 0.082(14) 0.087(11) 0.110(15) 0.022(11) 0.022(11) 0.008(11) C14' 0.075(10) 0.155(15) 0.137(14) 0.047(12) -0.029(12) 0.003(12) O13' 0.072(8) 0.210(13) 0.181(13) 0.094(13) 0.040(9) 0.057(8) _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 C3 1.974(15) . ? C1 C2 1.47(2) . ? C2 O2 1.193(16) . ? C2 C3 1.56(2) . ? C3 C4 1.466(18) . ? C3 C5 1.509(19) . ? C4 O1' 1.419(14) . ? C4 O4 1.445(16) . ? O1' C1' 1.395(13) . ? O4 C6 1.51(2) . ? C6 C7 1.67(5) . ? C6 C8 1.98(4) . ? C7 C8 1.33(5) . ? C1' O5' 1.419(13) . ? C1' C2' 1.494(15) . ? C2' O2' 1.452(13) . ? C2' C3' 1.526(15) . ? O2' C7' 1.298(15) . ? C3' O3' 1.433(12) . ? C3' C4' 1.507(15) . ? O3' C9' 1.344(17) . ? C4' O4' 1.412(12) . ? C4' C5' 1.505(14) . ? O4' C11' 1.342(15) . ? C5' O5' 1.434(12) . ? C5' C6' 1.544(15) . ? C6' O6' 1.432(13) . ? O6' C13' 1.317(18) . ? C7' O7' 1.167(15) . ? C7' C8' 1.54(2) . ? C9' O9' 1.192(16) . ? C9' C10' 1.480(18) . ? C11' O11' 1.192(16) . ? C11' C12' 1.476(17) . ? C13' O13' 1.164(17) . ? C13' C14' 1.480(18) . ? 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 O2 C2 C1 123.5(18) . . ? O2 C2 C3 117.7(18) . . ? C1 C2 C3 118.8(14) . . ? C4 C3 C5 112.8(12) . . ? C4 C3 C2 110.5(15) . . ? C5 C3 C2 114.2(13) . . ? C4 C3 Br1 106.5(11) . . ? C5 C3 Br1 107.2(13) . . ? C2 C3 Br1 105.0(10) . . ? O1' C4 O4 109.0(11) . . ? O1' C4 C3 112.6(13) . . ? O4 C4 C3 107.0(14) . . ? C1' O1' C4 117.4(11) . . ? C4 O4 C6 121.9(15) . . ? O4 C6 C7 109(2) . . ? O4 C6 C8 96.2(15) . . ? C7 C6 C8 41.5(16) . . ? C8 C7 C6 82(3) . . ? C7 C8 C6 57(3) . . ? O1' C1' O5' 106.3(10) . . ? O1' C1' C2' 107.1(11) . . ? O5' C1' C2' 105.2(10) . . ? O2' C2' C1' 107.8(10) . . ? O2' C2' C3' 106.9(11) . . ? C1' C2' C3' 109.9(10) . . ? C7' O2' C2' 116.0(11) . . ? O3' C3' C4' 107.9(9) . . ? O3' C3' C2' 107.6(10) . . ? C4' C3' C2' 111.3(11) . . ? C9' O3' C3' 116.7(10) . . ? O4' C4' C5' 108.5(9) . . ? O4' C4' C3' 107.1(10) . . ? C5' C4' C3' 109.4(9) . . ? C11' O4' C4' 119.0(10) . . ? O5' C5' C4' 108.4(9) . . ? O5' C5' C6' 105.0(10) . . ? C4' C5' C6' 115.7(10) . . ? C1' O5' C5' 111.7(9) . . ? O6' C6' C5' 107.7(10) . . ? C13' O6' C6' 114.9(11) . . ? O7' C7' O2' 127.9(16) . . ? O7' C7' C8' 122.1(15) . . ? O2' C7' C8' 109.2(14) . . ? O9' C9' O3' 123.7(16) . . ? O9' C9' C10' 124.6(17) . . ? O3' C9' C10' 111.6(15) . . ? O11' C11' O4' 125.1(13) . . ? O11' C11' C12' 125.0(15) . . ? O4' C11' C12' 109.9(14) . . ? O13' C13' O6' 122.9(16) . . ? O13' C13' C14' 125.7(18) . . ? O6' C13' C14' 111.2(15) . . ? _diffrn_measured_fraction_theta_max 0.664 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.664 _refine_diff_density_max 0.291 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.058