# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef 'gy-ac.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 Br4 O8' _chemical_formula_weight 868.25 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 ? _symmetry_space_group_name_H-M ? 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 5.8136(2) _cell_length_b 20.7534(8) _cell_length_c 7.4685(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.620(4) _cell_angle_gamma 90.00 _cell_volume 875.75(6) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.646 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 4.642 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _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 5739 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 29.46 _reflns_number_total 2097 _reflns_number_gt 1776 _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.3137P] 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 2097 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0655 _refine_ls_wR_factor_gt 0.0610 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.269 _refine_ls_shift/su_mean 0.018 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 1.39367(4) 0.707955(12) 0.78218(3) 0.03206(10) Uani 1 1 d . . . C4 C 0.8586(3) 0.57938(10) 0.7791(3) 0.0182(4) Uani 1 1 d . . . C1 C 1.1387(3) 0.64979(10) 0.7419(3) 0.0207(4) Uani 1 1 d . . . C2 C 1.0067(3) 0.63062(10) 0.5502(3) 0.0181(4) Uani 1 1 d . . . C3 C 0.8327(4) 0.58370(10) 0.5965(3) 0.0184(4) Uani 1 1 d . . . H3A H 0.7217 0.5607 0.5099 0.022 Uiso 1 1 calc R . . C5 C 1.0537(4) 0.62103(10) 0.8725(3) 0.0224(5) Uani 1 1 d . . . H5A H 1.1080 0.6264 0.9991 0.027 Uiso 1 1 calc R . . O1 O 0.5463(3) 0.50678(7) 0.7800(2) 0.0257(3) Uani 1 1 d . . . O2 O 0.7437(3) 0.54860(8) 1.0474(2) 0.0327(4) Uani 1 1 d . . . C8 C 0.7082(4) 0.54268(10) 0.8752(3) 0.0201(4) Uani 1 1 d . . . C7 C 1.1696(4) 0.60008(11) 0.4400(3) 0.0234(5) Uani 1 1 d . . . H7A H 1.2507 0.5640 0.5068 0.035 Uiso 1 1 calc R . . H7B H 1.2832 0.6314 0.4210 0.035 Uiso 1 1 calc R . . H7C H 1.0770 0.5857 0.3229 0.035 Uiso 1 1 calc R . . C6 C 0.8749(4) 0.68867(12) 0.4453(4) 0.0322(5) Uani 1 1 d . . . H6A H 0.7733 0.7073 0.5157 0.048 Uiso 1 1 calc R . . H6B H 0.7817 0.6746 0.3281 0.048 Uiso 1 1 calc R . . H6C H 0.9876 0.7203 0.4267 0.048 Uiso 1 1 calc R . . H1 H 0.417(9) 0.482(3) 0.864(8) 0.16(2) Uiso 1 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 0.03153(15) 0.03188(16) 0.03792(15) -0.01385(10) 0.01849(10) -0.01721(10) C4 0.0187(10) 0.0174(10) 0.0185(10) 0.0007(7) 0.0044(8) -0.0014(8) C1 0.0196(10) 0.0185(11) 0.0255(11) -0.0046(8) 0.0088(8) -0.0048(8) C2 0.0180(9) 0.0192(10) 0.0178(9) 0.0024(8) 0.0055(8) 0.0000(8) C3 0.0172(9) 0.0191(11) 0.0180(9) 0.0016(8) 0.0025(7) -0.0003(8) C5 0.0250(11) 0.0265(12) 0.0159(10) -0.0053(8) 0.0056(8) -0.0060(9) O1 0.0253(8) 0.0308(9) 0.0208(8) 0.0000(6) 0.0052(6) -0.0119(7) O2 0.0371(9) 0.0450(11) 0.0160(7) -0.0005(7) 0.0059(7) -0.0189(8) C8 0.0210(10) 0.0217(11) 0.0176(9) 0.0015(8) 0.0046(8) -0.0007(9) C7 0.0224(10) 0.0291(12) 0.0190(10) -0.0024(9) 0.0056(8) -0.0008(9) C6 0.0279(12) 0.0315(13) 0.0393(13) 0.0162(11) 0.0123(10) 0.0067(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 C1 1.880(2) . ? C4 C3 1.340(3) . ? C4 C5 1.465(3) . ? C4 C8 1.468(3) . ? C1 C5 1.334(3) . ? C1 C2 1.510(3) . ? C2 C3 1.502(3) . ? C2 C7 1.531(3) . ? C2 C6 1.540(3) . ? O1 C8 1.277(2) . ? O2 C8 1.260(2) . ? 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 C3 C4 C5 109.51(18) . . ? C3 C4 C8 126.54(19) . . ? C5 C4 C8 123.83(17) . . ? C5 C1 C2 112.48(18) . . ? C5 C1 Br1 125.76(16) . . ? C2 C1 Br1 121.77(14) . . ? C3 C2 C1 99.92(15) . . ? C3 C2 C7 113.01(18) . . ? C1 C2 C7 112.24(16) . . ? C3 C2 C6 110.05(17) . . ? C1 C2 C6 110.94(18) . . ? C7 C2 C6 110.31(17) . . ? C4 C3 C2 110.94(18) . . ? C1 C5 C4 107.14(18) . . ? O2 C8 O1 123.18(19) . . ? O2 C8 C4 118.38(18) . . ? O1 C8 C4 118.44(18) . . ? _diffrn_measured_fraction_theta_max 0.863 _diffrn_reflns_theta_full 29.46 _diffrn_measured_fraction_theta_full 0.863 _refine_diff_density_max 0.367 _refine_diff_density_min -0.510 _refine_diff_density_rms 0.072 _database_code_depnum_ccdc_archive 'CCDC 935030' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1a #TrackingRef 'gy-sq.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H20 Br O4' _chemical_formula_weight 344.22 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 ? _symmetry_space_group_name_H-M ? 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 5.76610(10) _cell_length_b 11.1691(2) _cell_length_c 22.7520(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.966(2) _cell_angle_gamma 90.00 _cell_volume 1464.42(5) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 2.818 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _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 21381 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 29.46 _reflns_number_total 3762 _reflns_number_gt 3152 _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+4.5624P] 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 3762 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_ref 0.1114 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Br1 Br 1.28270(6) 0.89456(3) 0.081864(14) 0.02740(11) Uani 1 1 d . . . O2 O 0.9142(4) 0.4069(2) 0.21154(11) 0.0319(6) Uani 1 1 d . . . O1 O 1.1735(4) 0.5591(2) 0.22159(9) 0.0246(5) Uani 1 1 d . . . C6 C 1.1618(5) 0.5935(3) 0.08968(13) 0.0192(6) Uani 1 1 d . . . H6A H 1.2097 0.5705 0.0508 0.023 Uiso 1 1 calc R . . H6B H 1.2937 0.6303 0.1102 0.023 Uiso 1 1 calc R . . C1 C 1.0350(5) 0.7990(3) 0.05323(13) 0.0203(6) Uani 1 1 d . . . C9 C 0.7993(5) 0.6014(3) 0.17786(14) 0.0270(7) Uani 1 1 d . . . H9A H 0.7515 0.6232 0.2169 0.032 Uiso 1 1 calc R . . H9B H 0.6676 0.5649 0.1571 0.032 Uiso 1 1 calc R . . C4 C 0.7685(5) 0.6448(3) 0.04194(13) 0.0190(6) Uani 1 1 d . . . H4A H 0.8070 0.5675 0.0254 0.023 Uiso 1 1 calc R . . H4B H 0.6266 0.6360 0.0632 0.023 Uiso 1 1 calc R . . C2 C 0.9036(6) 0.8230(3) 0.00528(13) 0.0227(6) Uani 1 1 d . . . H2A H 0.9160 0.8892 -0.0192 0.027 Uiso 1 1 calc R . . C3 C 0.7358(5) 0.7248(3) -0.00149(13) 0.0213(6) Uani 1 1 d . . . C10 C 0.8713(5) 0.7142(3) 0.14510(13) 0.0231(6) Uani 1 1 d . . . H10A H 0.9914 0.7554 0.1681 0.028 Uiso 1 1 calc R . . H10B H 0.7390 0.7675 0.1408 0.028 Uiso 1 1 calc R . . C5 C 0.9625(5) 0.6854(3) 0.08367(12) 0.0177(5) Uani 1 1 d . . . C7 C 1.0891(5) 0.4814(3) 0.12327(13) 0.0214(6) Uani 1 1 d . . . H7A H 0.9713 0.4388 0.1001 0.026 Uiso 1 1 calc R . . H7B H 1.2221 0.4289 0.1287 0.026 Uiso 1 1 calc R . . C8 C 0.9945(5) 0.5122(3) 0.18300(13) 0.0221(6) Uani 1 1 d . . . C11 C 1.2786(6) 0.4584(3) 0.25078(16) 0.0300(7) Uani 1 1 d . . . H11A H 1.3207 0.4776 0.2913 0.036 Uiso 1 1 calc R . . H11B H 1.4166 0.4329 0.2310 0.036 Uiso 1 1 calc R . . C12 C 1.0940(8) 0.3624(4) 0.2475(2) 0.0571(14) Uani 1 1 d . . . H12A H 1.1557 0.2894 0.2311 0.069 Uiso 1 1 calc R . . H12B H 1.0391 0.3450 0.2864 0.069 Uiso 1 1 calc R . . O3 O 0.4192(4) 0.6341(2) -0.05446(11) 0.0319(5) Uani 1 1 d . . . O4 O 0.5842(6) 0.8022(2) -0.08978(12) 0.0490(8) Uani 1 1 d . . . C13 C 0.5588(6) 0.7137(3) -0.04981(14) 0.0264(7) Uani 1 1 d . . . C14 C 0.4336(9) 0.8001(4) -0.14239(19) 0.0539(12) Uani 1 1 d . . . H14A H 0.3858 0.7184 -0.1508 0.065 Uiso 1 1 calc R . . H14B H 0.5178 0.8296 -0.1756 0.065 Uiso 1 1 calc R . . C15 C 0.2320(9) 0.8735(6) -0.1342(2) 0.078(2) Uani 1 1 d . . . H15A H 0.1340 0.8713 -0.1691 0.116 Uiso 1 1 calc R . . H15B H 0.2796 0.9544 -0.1264 0.116 Uiso 1 1 calc R . . H15C H 0.1480 0.8436 -0.1016 0.116 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 0.02959(18) 0.02151(16) 0.03029(18) 0.00071(12) -0.01075(12) -0.00422(12) O2 0.0274(12) 0.0373(13) 0.0302(13) 0.0160(10) -0.0097(10) -0.0134(10) O1 0.0260(11) 0.0264(11) 0.0208(11) 0.0049(9) -0.0089(9) -0.0034(9) C6 0.0171(13) 0.0206(14) 0.0196(14) 0.0009(11) -0.0010(10) 0.0026(11) C1 0.0211(14) 0.0168(13) 0.0226(14) -0.0018(11) -0.0040(11) -0.0004(11) C9 0.0188(14) 0.0428(19) 0.0196(14) 0.0073(14) 0.0028(11) 0.0018(14) C4 0.0166(13) 0.0226(14) 0.0178(14) -0.0021(11) -0.0011(10) 0.0027(11) C2 0.0316(16) 0.0174(13) 0.0187(14) 0.0008(11) -0.0049(12) 0.0005(12) C3 0.0226(14) 0.0209(14) 0.0200(14) -0.0030(11) -0.0070(11) 0.0034(12) C10 0.0226(15) 0.0274(15) 0.0193(14) -0.0010(12) -0.0013(11) 0.0091(12) C5 0.0168(13) 0.0198(13) 0.0164(13) 0.0010(11) -0.0020(10) 0.0010(11) C7 0.0214(14) 0.0210(14) 0.0213(15) 0.0028(11) -0.0051(11) 0.0005(11) C8 0.0187(14) 0.0280(15) 0.0192(14) 0.0063(12) -0.0051(11) -0.0051(12) C11 0.0265(16) 0.0356(18) 0.0271(16) 0.0130(14) -0.0093(13) -0.0042(14) C12 0.048(2) 0.055(3) 0.066(3) 0.037(2) -0.034(2) -0.025(2) O3 0.0270(12) 0.0360(13) 0.0319(13) -0.0005(10) -0.0120(10) -0.0044(10) O4 0.080(2) 0.0226(12) 0.0416(15) 0.0081(11) -0.0422(15) -0.0081(13) C13 0.0311(17) 0.0221(15) 0.0253(16) -0.0043(12) -0.0114(13) 0.0071(13) C14 0.079(3) 0.039(2) 0.041(2) 0.0057(18) -0.035(2) -0.001(2) C15 0.055(3) 0.122(5) 0.054(3) -0.033(3) -0.025(2) 0.039(3) _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 C1 1.882(3) . ? O2 C12 1.391(4) . ? O2 C8 1.428(4) . ? O1 C11 1.430(4) . ? O1 C8 1.431(3) . ? C6 C7 1.532(4) . ? C6 C5 1.543(4) . ? C1 C2 1.334(4) . ? C1 C5 1.511(4) . ? C9 C8 1.505(4) . ? C9 C10 1.528(5) . ? C4 C3 1.340(4) . ? C4 C5 1.512(4) . ? C2 C3 1.467(4) . ? C3 C13 1.479(4) . ? C10 C5 1.544(4) . ? C7 C8 1.521(4) . ? C11 C12 1.511(5) . ? O3 C13 1.201(4) . ? O4 C13 1.354(4) . ? O4 C14 1.454(4) . ? C14 C15 1.439(7) . ? 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 C12 O2 C8 108.3(3) . . ? C11 O1 C8 106.4(2) . . ? C7 C6 C5 111.8(2) . . ? C2 C1 C5 112.7(3) . . ? C2 C1 Br1 124.9(2) . . ? C5 C1 Br1 122.4(2) . . ? C8 C9 C10 111.6(3) . . ? C3 C4 C5 110.2(3) . . ? C1 C2 C3 106.8(3) . . ? C4 C3 C2 110.2(3) . . ? C4 C3 C13 124.6(3) . . ? C2 C3 C13 125.2(3) . . ? C9 C10 C5 112.1(3) . . ? C4 C5 C1 100.0(2) . . ? C4 C5 C6 112.9(2) . . ? C1 C5 C6 112.5(2) . . ? C4 C5 C10 111.3(2) . . ? C1 C5 C10 110.4(2) . . ? C6 C5 C10 109.5(2) . . ? C8 C7 C6 112.0(2) . . ? O2 C8 O1 105.1(2) . . ? O2 C8 C9 109.1(3) . . ? O1 C8 C9 109.1(3) . . ? O2 C8 C7 110.6(3) . . ? O1 C8 C7 111.0(2) . . ? C9 C8 C7 111.7(2) . . ? O1 C11 C12 104.4(3) . . ? O2 C12 C11 106.6(3) . . ? C13 O4 C14 117.8(3) . . ? O3 C13 O4 124.6(3) . . ? O3 C13 C3 124.8(3) . . ? O4 C13 C3 110.5(3) . . ? O4 C14 C15 110.3(4) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 29.46 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 1.891 _refine_diff_density_min -0.982 _refine_diff_density_rms 0.099 _database_code_depnum_ccdc_archive 'CCDC 935031'