# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email chmyyy@nus.edu.sg _publ_contact_author_name 'Ying-Yeung Yeung' loop_ _publ_author_name 'Chong Kiat Tan' 'Chen Cheng Le' 'Ying-Yeung Yeung' data_b665 _database_code_depnum_ccdc_archive 'CCDC 864876' #TrackingRef 'web_deposit_cif_file_0_ChongKiatTan_1327919752.B665.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H11 Br O2' _chemical_formula_weight 255.11 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 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 8.7478(7) _cell_length_b 11.7579(10) _cell_length_c 10.7912(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.206(2) _cell_angle_gamma 90.00 _cell_volume 1065.83(15) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 2337 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 24.56 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 3.827 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2073 _exptl_absorpt_correction_T_max 0.2506 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 7484 _diffrn_reflns_av_R_equivalents 0.0341 _diffrn_reflns_av_sigmaI/netI 0.0772 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4800 _reflns_number_gt 3699 _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^)+(0.0380P)^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 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 0.030(13) _refine_ls_number_reflns 4800 _refine_ls_number_parameters 253 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 0.965 _refine_ls_restrained_S_all 0.965 _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 0.46733(6) 0.44112(4) 0.79985(4) 0.04846(18) Uani 1 1 d . . . Br2 Br 0.47892(6) 0.38728(3) 0.30787(4) 0.04650(17) Uani 1 1 d . . . O1 O 0.4726(4) 0.5898(3) 0.5687(3) 0.0380(8) Uani 1 1 d . . . O2 O 0.3588(5) 0.6657(4) 0.3775(4) 0.0604(12) Uani 1 1 d . . . O3 O 0.4685(4) 0.2504(3) 0.0622(3) 0.0420(9) Uani 1 1 d . . . O4 O 0.3516(5) 0.1404(3) -0.1042(3) 0.0558(11) Uani 1 1 d . . . C1 C 0.6426(5) 0.4616(4) 0.7188(4) 0.0360(10) Uani 1 1 d . . . H1 H 0.6299 0.4041 0.6496 0.043 Uiso 1 1 calc R . . C2 C 0.6303(5) 0.5773(4) 0.6588(4) 0.0368(11) Uani 1 1 d . . . H2 H 0.6468 0.6363 0.7267 0.044 Uiso 1 1 calc R . . C3 C 0.4800(7) 0.6427(5) 0.4594(5) 0.0403(13) Uani 1 1 d . . . C4 C 0.6468(6) 0.6651(5) 0.4622(5) 0.0492(15) Uani 1 1 d . . . H4A H 0.6711 0.7464 0.4739 0.059 Uiso 1 1 calc R . . H4B H 0.6677 0.6396 0.3820 0.059 Uiso 1 1 calc R . . C5 C 0.7444(6) 0.5975(6) 0.5761(5) 0.0509(15) Uani 1 1 d . . . H5A H 0.8381 0.6407 0.6241 0.061 Uiso 1 1 calc R . . H5B H 0.7795 0.5253 0.5478 0.061 Uiso 1 1 calc R . . C6 C 0.8002(5) 0.4414(4) 0.8176(4) 0.0326(10) Uani 1 1 d . . . C7 C 0.8907(6) 0.3494(4) 0.8018(4) 0.0440(13) Uani 1 1 d . . . H7 H 0.8526 0.2992 0.7322 0.053 Uiso 1 1 calc R . . C8 C 1.0375(6) 0.3313(6) 0.8890(5) 0.0557(16) Uani 1 1 d . . . H8 H 1.0988 0.2683 0.8786 0.067 Uiso 1 1 calc R . . C9 C 1.0950(6) 0.4039(7) 0.9904(5) 0.063(2) Uani 1 1 d . . . H9 H 1.1953 0.3908 1.0489 0.075 Uiso 1 1 calc R . . C10 C 1.0057(7) 0.4960(6) 1.0064(5) 0.0560(16) Uani 1 1 d . . . H10 H 1.0447 0.5463 1.0759 0.067 Uiso 1 1 calc R . . C11 C 0.8594(6) 0.5142(5) 0.9205(4) 0.0487(13) Uani 1 1 d . . . H11 H 0.7983 0.5771 0.9318 0.058 Uiso 1 1 calc R . . C12 C 0.6535(5) 0.3003(4) 0.2660(4) 0.0348(9) Uani 1 1 d . . . H12 H 0.6497 0.2211 0.2963 0.042 Uiso 1 1 calc R . . C13 C 0.6263(5) 0.2973(4) 0.1206(4) 0.0394(11) Uani 1 1 d . . . H13 H 0.6333 0.3751 0.0877 0.047 Uiso 1 1 calc R . . C14 C 0.4723(7) 0.1799(5) -0.0367(5) 0.0392(13) Uani 1 1 d . . . C15 C 0.6397(6) 0.1635(5) -0.0418(5) 0.0461(14) Uani 1 1 d . . . H15A H 0.6564 0.1997 -0.1188 0.055 Uiso 1 1 calc R . . H15B H 0.6651 0.0824 -0.0430 0.055 Uiso 1 1 calc R . . C16 C 0.7416(6) 0.2196(6) 0.0799(5) 0.0491(15) Uani 1 1 d . . . H16A H 0.7864 0.1629 0.1467 0.059 Uiso 1 1 calc R . . H16B H 0.8287 0.2631 0.0621 0.059 Uiso 1 1 calc R . . C17 C 0.8110(6) 0.3511(4) 0.3393(4) 0.0335(11) Uani 1 1 d . . . C18 C 0.8715(6) 0.4473(5) 0.2968(4) 0.0474(13) Uani 1 1 d . . . H18 H 0.8149 0.4823 0.2193 0.057 Uiso 1 1 calc R . . C19 C 1.0160(7) 0.4925(6) 0.3685(5) 0.0575(17) Uani 1 1 d . . . H19 H 1.0575 0.5577 0.3392 0.069 Uiso 1 1 calc R . . C20 C 1.0988(6) 0.4410(7) 0.4832(5) 0.0563(16) Uani 1 1 d . . . H20 H 1.1972 0.4705 0.5317 0.068 Uiso 1 1 calc R . . C21 C 1.0367(7) 0.3479(6) 0.5248(5) 0.0575(18) Uani 1 1 d . . . H21 H 1.0913 0.3145 0.6039 0.069 Uiso 1 1 calc R . . C22 C 0.8951(6) 0.3008(5) 0.4538(4) 0.0441(13) Uani 1 1 d . . . H22 H 0.8558 0.2347 0.4831 0.053 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 0.0296(3) 0.0640(4) 0.0486(3) 0.0132(3) 0.0056(2) -0.0038(3) Br2 0.0328(3) 0.0554(3) 0.0499(3) -0.0114(2) 0.0092(2) 0.0020(3) O1 0.0244(18) 0.046(2) 0.0420(18) 0.0076(17) 0.0075(15) 0.0039(16) O2 0.049(2) 0.074(3) 0.054(2) 0.0171(19) 0.0054(19) 0.018(2) O3 0.0266(19) 0.053(2) 0.0437(18) -0.0115(18) 0.0046(16) -0.0032(18) O4 0.039(2) 0.060(3) 0.060(2) -0.0226(19) 0.0003(19) -0.0137(19) C1 0.027(2) 0.043(3) 0.035(2) -0.0026(18) 0.0039(18) 0.003(2) C2 0.023(2) 0.042(3) 0.041(2) -0.0031(19) 0.001(2) 0.002(2) C3 0.042(3) 0.037(3) 0.045(3) 0.006(2) 0.017(3) 0.008(3) C4 0.046(3) 0.052(4) 0.055(3) 0.012(3) 0.024(3) 0.000(3) C5 0.027(3) 0.070(4) 0.055(3) 0.010(3) 0.010(3) 0.000(3) C6 0.025(2) 0.036(2) 0.0346(19) -0.003(2) 0.0059(17) -0.004(2) C7 0.033(3) 0.050(3) 0.045(3) 0.002(2) 0.006(2) 0.006(2) C8 0.034(3) 0.060(4) 0.071(4) 0.015(3) 0.010(3) 0.014(3) C9 0.027(3) 0.086(5) 0.063(3) 0.015(4) -0.008(3) -0.008(3) C10 0.038(3) 0.079(4) 0.046(3) -0.011(3) 0.002(2) -0.013(3) C11 0.035(3) 0.059(3) 0.050(3) -0.005(3) 0.008(2) 0.002(3) C12 0.027(2) 0.038(2) 0.038(2) -0.0020(18) 0.0072(18) 0.0021(19) C13 0.033(3) 0.046(3) 0.036(2) -0.002(2) 0.0037(19) -0.005(2) C14 0.033(3) 0.044(3) 0.037(3) 0.001(2) 0.006(2) -0.001(3) C15 0.043(3) 0.052(3) 0.045(3) -0.009(3) 0.015(3) 0.000(3) C16 0.032(3) 0.067(4) 0.051(3) -0.010(3) 0.015(3) -0.002(3) C17 0.031(3) 0.033(2) 0.033(2) -0.0029(17) 0.0037(19) 0.0019(19) C18 0.046(3) 0.050(3) 0.036(2) 0.010(2) -0.005(2) 0.005(3) C19 0.048(4) 0.065(4) 0.056(3) 0.002(3) 0.010(3) -0.014(3) C20 0.027(3) 0.090(4) 0.046(3) -0.014(3) 0.001(2) -0.004(3) C21 0.029(3) 0.089(5) 0.046(3) 0.007(3) -0.005(2) 0.013(3) C22 0.031(3) 0.057(3) 0.044(2) 0.014(2) 0.011(2) 0.008(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 Br1 C1 1.980(4) . ? Br2 C12 1.992(4) . ? O1 C3 1.350(6) . ? O1 C2 1.457(5) . ? O2 C3 1.207(6) . ? O3 C14 1.359(6) . ? O3 C13 1.456(5) . ? O4 C14 1.196(6) . ? C1 C2 1.498(6) . ? C1 C6 1.508(5) . ? C2 C5 1.532(7) . ? C3 C4 1.475(8) . ? C4 C5 1.511(7) . ? C6 C7 1.379(7) . ? C6 C11 1.383(6) . ? C7 C8 1.381(7) . ? C8 C9 1.368(9) . ? C9 C10 1.374(10) . ? C10 C11 1.371(7) . ? C12 C17 1.508(6) . ? C12 C13 1.520(6) . ? C13 C16 1.514(7) . ? C14 C15 1.494(8) . ? C15 C16 1.516(7) . ? C17 C18 1.380(7) . ? C17 C22 1.382(6) . ? C18 C19 1.390(7) . ? C19 C20 1.387(8) . ? C20 C21 1.353(10) . ? C21 C22 1.377(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 C3 O1 C2 111.2(4) . . ? C14 O3 C13 110.1(4) . . ? C2 C1 C6 112.9(4) . . ? C2 C1 Br1 109.3(3) . . ? C6 C1 Br1 109.7(3) . . ? O1 C2 C1 108.7(4) . . ? O1 C2 C5 104.2(3) . . ? C1 C2 C5 114.4(4) . . ? O2 C3 O1 119.8(5) . . ? O2 C3 C4 129.5(5) . . ? O1 C3 C4 110.6(4) . . ? C3 C4 C5 104.8(5) . . ? C4 C5 C2 104.1(4) . . ? C7 C6 C11 119.1(4) . . ? C7 C6 C1 118.6(4) . . ? C11 C6 C1 122.3(5) . . ? C6 C7 C8 119.5(5) . . ? C9 C8 C7 120.9(6) . . ? C8 C9 C10 119.8(5) . . ? C11 C10 C9 119.6(5) . . ? C10 C11 C6 121.1(5) . . ? C17 C12 C13 114.1(4) . . ? C17 C12 Br2 108.9(3) . . ? C13 C12 Br2 109.7(3) . . ? O3 C13 C16 105.9(4) . . ? O3 C13 C12 108.2(4) . . ? C16 C13 C12 112.9(4) . . ? O4 C14 O3 120.3(5) . . ? O4 C14 C15 129.5(5) . . ? O3 C14 C15 110.2(4) . . ? C14 C15 C16 104.9(4) . . ? C13 C16 C15 103.6(4) . . ? C18 C17 C22 119.3(4) . . ? C18 C17 C12 122.0(4) . . ? C22 C17 C12 118.7(4) . . ? C17 C18 C19 120.1(4) . . ? C20 C19 C18 119.8(6) . . ? C21 C20 C19 119.4(5) . . ? C20 C21 C22 121.5(5) . . ? C21 C22 C17 119.8(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.932 _refine_diff_density_min -0.648 _refine_diff_density_rms 0.087