# 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 ramchary.db@gmail.com _publ_contact_author_name 'Dhevalapally B. Ramachary' loop_ _publ_author_name 'Dhevalapally B. Ramachary' 'Chintalapudi Venkaiah' 'Patoju Murali Krishna' data_DBR _database_code_depnum_ccdc_archive 'CCDC 848633' #TrackingRef 'DBR-09-09-11.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_absolute_configuration rm _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H19 Br O3' _chemical_formula_weight 471.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.0571(2) _cell_length_b 11.5261(2) _cell_length_c 12.1322(2) _cell_angle_alpha 90.00 _cell_angle_beta 99.462(2) _cell_angle_gamma 90.00 _cell_volume 1111.35(4) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6410 _cell_measurement_theta_min 3.6905 _cell_measurement_theta_max 72.8134 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 2.727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3938 _exptl_absorpt_correction_T_max 0.5156 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9422 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 70.03 _reflns_number_total 3712 _reflns_number_gt 3457 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.1528P)^2^+0.1441P] 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 0.04(3) _refine_ls_number_reflns 3712 _refine_ls_number_parameters 281 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.1932 _refine_ls_wR_factor_gt 0.1877 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.38386(11) 0.60134(5) 0.38920(7) 0.1052(4) Uani 1 1 d . . . C1 C 0.3101(6) -0.0141(5) 0.0049(4) 0.0549(10) Uani 1 1 d . . . C2 C 0.1948(6) -0.0893(4) 0.0530(4) 0.0565(10) Uani 1 1 d . . . H2 H 0.1713 -0.1621 0.0211 0.068 Uiso 1 1 calc R . . C3 C 0.1203(5) -0.0598(4) 0.1409(3) 0.0467(8) Uani 1 1 d . . . C4 C 0.1552(4) 0.0554(4) 0.1983(3) 0.0426(8) Uani 1 1 d . . . C5 C 0.3256(4) 0.1108(4) 0.1768(3) 0.0439(8) Uani 1 1 d . . . H5 H 0.4166 0.0635 0.2177 0.053 Uiso 1 1 calc R . . C6 C 0.3448(4) 0.1066(4) 0.0529(3) 0.0460(8) Uani 1 1 d . . . H6 H 0.2600 0.1587 0.0122 0.055 Uiso 1 1 calc R . . C7 C 0.5164(6) 0.1500(6) 0.0343(4) 0.0668(13) Uani 1 1 d . . . H7A H 0.6023 0.0988 0.0707 0.100 Uiso 1 1 calc R . . H7B H 0.5350 0.2267 0.0649 0.100 Uiso 1 1 calc R . . H7C H 0.5202 0.1521 -0.0444 0.100 Uiso 1 1 calc R . . C8 C 0.3476(4) 0.2339(4) 0.2250(3) 0.0462(8) Uani 1 1 d . . . C9 C 0.4239(6) 0.2487(6) 0.3360(4) 0.0630(12) Uani 1 1 d . . . H9 H 0.4685 0.1844 0.3767 0.076 Uiso 1 1 calc R . . C10 C 0.4349(7) 0.3547(6) 0.3866(4) 0.0689(14) Uani 1 1 d . . . H10 H 0.4838 0.3627 0.4612 0.083 Uiso 1 1 calc R . . C11 C 0.3711(6) 0.4507(5) 0.3239(5) 0.0634(12) Uani 1 1 d . . . C12 C 0.2971(6) 0.4397(5) 0.2115(4) 0.0582(10) Uani 1 1 d . . . H12 H 0.2566 0.5043 0.1697 0.070 Uiso 1 1 calc R . . C13 C 0.2858(5) 0.3302(4) 0.1646(3) 0.0519(9) Uani 1 1 d . . . H13 H 0.2353 0.3212 0.0904 0.062 Uiso 1 1 calc R . . C14 C 0.1634(5) 0.0469(4) 0.3264(3) 0.0500(9) Uani 1 1 d . . . C15 C 0.0588(5) 0.1393(5) 0.3616(3) 0.0531(10) Uani 1 1 d . . . C16 C 0.0472(8) 0.1727(6) 0.4702(4) 0.0740(15) Uani 1 1 d . . . H16 H 0.1027 0.1322 0.5317 0.089 Uiso 1 1 calc R . . C17 C -0.0503(9) 0.2683(8) 0.4825(5) 0.0852(19) Uani 1 1 d . . . H17 H -0.0578 0.2948 0.5539 0.102 Uiso 1 1 calc R . . C18 C -0.1386(7) 0.3267(7) 0.3894(5) 0.0774(16) Uani 1 1 d . . . H18 H -0.2050 0.3902 0.4007 0.093 Uiso 1 1 calc R . . C19 C -0.1297(6) 0.2925(5) 0.2819(5) 0.0625(12) Uani 1 1 d . . . H19 H -0.1884 0.3315 0.2205 0.075 Uiso 1 1 calc R . . C20 C -0.0295(5) 0.1971(4) 0.2690(3) 0.0501(9) Uani 1 1 d . . . C21 C 0.0114(4) 0.1429(4) 0.1651(3) 0.0428(8) Uani 1 1 d . . . C22 C -0.0024(5) -0.1411(4) 0.1788(3) 0.0521(9) Uani 1 1 d . . . C23 C 0.0344(7) -0.2595(5) 0.1858(4) 0.0637(12) Uani 1 1 d . . . H23 H 0.1364 -0.2862 0.1692 0.076 Uiso 1 1 calc R . . C24 C -0.0800(9) -0.3375(6) 0.2174(4) 0.0763(16) Uani 1 1 d . . . H24 H -0.0538 -0.4161 0.2229 0.092 Uiso 1 1 calc R . . C25 C -0.2303(9) -0.2997(7) 0.2405(5) 0.0823(19) Uani 1 1 d . . . H25 H -0.3084 -0.3528 0.2586 0.099 Uiso 1 1 calc R . . C26 C -0.2672(8) -0.1830(8) 0.2369(7) 0.0894(19) Uani 1 1 d . . . H26 H -0.3693 -0.1578 0.2546 0.107 Uiso 1 1 calc R . . C27 C -0.1545(7) -0.1027(6) 0.2075(5) 0.0743(14) Uani 1 1 d . . . H27 H -0.1796 -0.0239 0.2069 0.089 Uiso 1 1 calc R . . O1 O 0.3678(6) -0.0453(4) -0.0773(4) 0.0782(11) Uani 1 1 d . . . O2 O 0.2499(5) -0.0227(4) 0.3848(3) 0.0647(8) Uani 1 1 d . . . O3 O -0.0555(4) 0.1640(3) 0.0705(2) 0.0548(7) Uani 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 0.1130(6) 0.0894(5) 0.1074(6) -0.0557(4) 0.0010(4) -0.0013(4) C1 0.060(2) 0.052(2) 0.055(2) -0.012(2) 0.0150(16) 0.0071(18) C2 0.070(2) 0.050(3) 0.0502(19) -0.0093(18) 0.0127(17) -0.0066(19) C3 0.0509(18) 0.048(2) 0.0407(15) 0.0034(16) 0.0047(13) -0.0031(16) C4 0.0451(16) 0.049(2) 0.0335(15) 0.0011(15) 0.0043(11) 0.0025(15) C5 0.0412(15) 0.050(2) 0.0390(15) 0.0056(15) 0.0007(12) 0.0029(15) C6 0.0447(16) 0.048(2) 0.0464(17) -0.0020(17) 0.0115(13) -0.0032(15) C7 0.056(2) 0.081(4) 0.068(2) -0.007(2) 0.0221(19) -0.012(2) C8 0.0431(16) 0.056(2) 0.0398(16) -0.0035(16) 0.0063(12) -0.0090(15) C9 0.060(2) 0.076(4) 0.048(2) -0.001(2) -0.0054(16) -0.006(2) C10 0.065(2) 0.086(4) 0.052(2) -0.025(3) -0.0032(18) -0.009(3) C11 0.058(2) 0.063(3) 0.070(3) -0.025(2) 0.0104(19) -0.014(2) C12 0.063(2) 0.054(3) 0.059(2) -0.009(2) 0.0146(17) -0.0067(19) C13 0.062(2) 0.053(2) 0.0414(16) -0.0033(17) 0.0083(15) -0.0072(18) C14 0.0570(19) 0.056(2) 0.0354(17) 0.0028(17) 0.0037(13) -0.0127(18) C15 0.060(2) 0.064(3) 0.0369(16) 0.0009(17) 0.0138(14) -0.0041(18) C16 0.098(4) 0.086(4) 0.0414(19) -0.008(2) 0.021(2) -0.008(3) C17 0.100(4) 0.102(5) 0.062(3) -0.025(3) 0.036(3) -0.005(4) C18 0.074(3) 0.080(4) 0.087(4) -0.020(3) 0.039(3) -0.003(3) C19 0.056(2) 0.070(3) 0.065(2) -0.005(2) 0.0184(18) 0.004(2) C20 0.0456(17) 0.058(3) 0.0486(18) -0.0020(18) 0.0126(14) -0.0038(17) C21 0.0454(17) 0.046(2) 0.0381(15) 0.0059(15) 0.0092(12) -0.0011(14) C22 0.060(2) 0.052(2) 0.0423(17) 0.0034(17) 0.0029(15) -0.0076(18) C23 0.088(3) 0.059(3) 0.0451(19) 0.002(2) 0.0124(18) -0.005(2) C24 0.112(5) 0.061(3) 0.055(2) 0.007(2) 0.011(2) -0.019(3) C25 0.101(4) 0.080(4) 0.061(3) 0.013(3) -0.001(3) -0.040(4) C26 0.059(3) 0.101(5) 0.108(5) 0.017(4) 0.015(3) -0.018(3) C27 0.065(3) 0.067(4) 0.092(4) 0.009(3) 0.018(2) -0.008(2) O1 0.103(3) 0.065(2) 0.078(2) -0.021(2) 0.048(2) -0.009(2) O2 0.0797(19) 0.064(2) 0.0463(14) 0.0129(16) -0.0009(13) 0.0038(17) O3 0.0593(15) 0.062(2) 0.0400(12) 0.0066(13) -0.0014(10) 0.0038(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C11 1.905(5) . ? C1 O1 1.222(6) . ? C1 C2 1.460(7) . ? C1 C6 1.516(7) . ? C2 C3 1.351(6) . ? C3 C22 1.488(6) . ? C3 C4 1.505(6) . ? C4 C21 1.539(5) . ? C4 C14 1.548(5) . ? C4 C5 1.574(5) . ? C5 C8 1.535(6) . ? C5 C6 1.537(5) . ? C6 C7 1.521(5) . ? C8 C13 1.377(7) . ? C8 C9 1.396(5) . ? C9 C10 1.363(9) . ? C10 C11 1.392(10) . ? C11 C12 1.401(7) . ? C12 C13 1.382(7) . ? C14 O2 1.213(6) . ? C14 C15 1.465(7) . ? C15 C16 1.390(6) . ? C15 C20 1.396(6) . ? C16 C17 1.375(11) . ? C17 C18 1.404(11) . ? C18 C19 1.376(8) . ? C19 C20 1.388(7) . ? C20 C21 1.491(5) . ? C21 O3 1.210(5) . ? C22 C23 1.396(8) . ? C22 C27 1.400(8) . ? C23 C24 1.386(8) . ? C24 C25 1.358(11) . ? C25 C26 1.377(12) . ? C26 C27 1.384(9) . ? 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 O1 C1 C2 120.2(5) . . ? O1 C1 C6 120.8(5) . . ? C2 C1 C6 118.7(4) . . ? C3 C2 C1 124.1(4) . . ? C2 C3 C22 119.3(4) . . ? C2 C3 C4 120.9(4) . . ? C22 C3 C4 119.7(4) . . ? C3 C4 C21 112.5(3) . . ? C3 C4 C14 112.5(3) . . ? C21 C4 C14 102.1(3) . . ? C3 C4 C5 112.5(3) . . ? C21 C4 C5 109.3(3) . . ? C14 C4 C5 107.3(3) . . ? C8 C5 C6 112.2(3) . . ? C8 C5 C4 111.2(3) . . ? C6 C5 C4 112.3(3) . . ? C1 C6 C7 111.1(4) . . ? C1 C6 C5 111.2(4) . . ? C7 C6 C5 112.0(3) . . ? C13 C8 C9 118.6(4) . . ? C13 C8 C5 122.2(3) . . ? C9 C8 C5 119.1(4) . . ? C10 C9 C8 122.0(5) . . ? C9 C10 C11 118.3(4) . . ? C10 C11 C12 121.3(5) . . ? C10 C11 Br1 120.5(4) . . ? C12 C11 Br1 118.2(5) . . ? C13 C12 C11 118.2(5) . . ? C8 C13 C12 121.5(4) . . ? O2 C14 C15 127.9(4) . . ? O2 C14 C4 123.7(4) . . ? C15 C14 C4 108.4(3) . . ? C16 C15 C20 121.7(5) . . ? C16 C15 C14 127.5(5) . . ? C20 C15 C14 110.7(3) . . ? C17 C16 C15 116.9(6) . . ? C16 C17 C18 121.3(5) . . ? C19 C18 C17 121.8(6) . . ? C18 C19 C20 117.1(5) . . ? C19 C20 C15 121.1(4) . . ? C19 C20 C21 129.9(4) . . ? C15 C20 C21 109.0(4) . . ? O3 C21 C20 126.2(4) . . ? O3 C21 C4 125.4(4) . . ? C20 C21 C4 108.4(3) . . ? C23 C22 C27 118.7(5) . . ? C23 C22 C3 119.3(4) . . ? C27 C22 C3 122.1(5) . . ? C24 C23 C22 120.4(6) . . ? C25 C24 C23 120.3(6) . . ? C24 C25 C26 120.2(5) . . ? C25 C26 C27 120.9(7) . . ? C26 C27 C22 119.4(6) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 70.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.517 _refine_diff_density_min -0.554 _refine_diff_density_rms 0.054 # Attachment 'dbr12a.cif' data_dbr12a _database_code_depnum_ccdc_archive 'CCDC 848634' #TrackingRef 'dbr12a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H19 Br O3' _chemical_formula_weight 471.33 _chemical_absolute_configuration rm loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(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 8.5036(15) _cell_length_b 12.3169(10) _cell_length_c 21.639(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2266.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1099 _cell_measurement_theta_min 3.5855 _cell_measurement_theta_max 44.9664 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 2.674 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3997 _exptl_absorpt_correction_T_max 0.6168 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\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 10845 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0353 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 73.11 _reflns_number_total 4488 _reflns_number_gt 3736 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) ; _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^)+(0.0481P)^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 SHELXL _refine_ls_extinction_coef 0.00049(14) _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 0.003(17) _refine_ls_number_reflns 4488 _refine_ls_number_parameters 286 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.035 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.10097(7) 0.20823(3) 0.97448(2) 0.09584(17) Uani 1 1 d . . . O1 O -0.3451(3) 0.81828(19) 0.75765(12) 0.0800(6) Uani 1 1 d . . . O2 O 0.1406(3) 0.64450(19) 0.75530(9) 0.0703(5) Uani 1 1 d . . . O3 O 0.1222(3) 0.78403(17) 0.95824(9) 0.0717(5) Uani 1 1 d . . . C1 C 0.0329(3) 0.8427(2) 0.82743(12) 0.0527(5) Uani 1 1 d . . . C2 C -0.1009(4) 0.8680(2) 0.79770(13) 0.0612(6) Uani 1 1 d . . . H2 H -0.1133 0.9390 0.7839 0.073 Uiso 1 1 calc R . . C3 C -0.2276(3) 0.7916(3) 0.78563(13) 0.0592(6) Uani 1 1 d . . . C4 C -0.2076(3) 0.6775(2) 0.80807(14) 0.0608(6) Uani 1 1 d . . . H4A H -0.1612 0.6339 0.7755 0.073 Uiso 1 1 calc R . . H4B H -0.3099 0.6471 0.8178 0.073 Uiso 1 1 calc R . . C5 C -0.1025(3) 0.67262(19) 0.86558(11) 0.0506(5) Uani 1 1 d . . . C6 C 0.0584(3) 0.72873(19) 0.85285(11) 0.0481(5) Uani 1 1 d . . . C7 C 0.1579(3) 0.9243(2) 0.83535(13) 0.0555(6) Uani 1 1 d . . . C8 C 0.1210(4) 1.0310(2) 0.85144(14) 0.0637(6) Uani 1 1 d . . . H8 H 0.0166 1.0501 0.8581 0.076 Uiso 1 1 calc R . . C9 C 0.2374(4) 1.1088(2) 0.85762(15) 0.0694(8) Uani 1 1 d . . . H9 H 0.2092 1.1791 0.8686 0.083 Uiso 1 1 calc R . . C10 C 0.3922(4) 1.0853(2) 0.84798(12) 0.0637(7) Uani 1 1 d . . . C11 C 0.4292(4) 0.9794(3) 0.83213(17) 0.0749(8) Uani 1 1 d . . . H11 H 0.5338 0.9609 0.8253 0.090 Uiso 1 1 calc R . . C12 C 0.3147(4) 0.9007(3) 0.82618(18) 0.0730(8) Uani 1 1 d . . . H12 H 0.3439 0.8303 0.8158 0.088 Uiso 1 1 calc R . . C13 C -0.0929(3) 0.55727(19) 0.89128(11) 0.0487(5) Uani 1 1 d . . . C14 C -0.0830(3) 0.4673(2) 0.85304(11) 0.0551(6) Uani 1 1 d . . . H14 H -0.0764 0.4770 0.8105 0.066 Uiso 1 1 calc R . . C15 C -0.0827(4) 0.3632(2) 0.87717(13) 0.0618(6) Uani 1 1 d . . . H15 H -0.0763 0.3033 0.8511 0.074 Uiso 1 1 calc R . . C16 C -0.0920(4) 0.3496(2) 0.94019(13) 0.0628(6) Uani 1 1 d . . . C17 C -0.1012(5) 0.4375(2) 0.97959(12) 0.0683(7) Uani 1 1 d . . . H17 H -0.1082 0.4274 1.0221 0.082 Uiso 1 1 calc R . . C18 C -0.0998(4) 0.5409(2) 0.95474(12) 0.0598(6) Uani 1 1 d . . . H18 H -0.1035 0.6006 0.9810 0.072 Uiso 1 1 calc R . . C19 C 0.1593(3) 0.65603(19) 0.81055(11) 0.0501(5) Uani 1 1 d . . . C20 C 0.2798(3) 0.6038(2) 0.84947(14) 0.0533(6) Uani 1 1 d . . . C21 C 0.3868(4) 0.5226(2) 0.83478(19) 0.0744(9) Uani 1 1 d . . . H21 H 0.3913 0.4930 0.7953 0.089 Uiso 1 1 calc R . . C22 C 0.4865(4) 0.4875(3) 0.8812(3) 0.0946(15) Uani 1 1 d . . . H22 H 0.5601 0.4338 0.8723 0.114 Uiso 1 1 calc R . . C23 C 0.4798(4) 0.5303(3) 0.9412(3) 0.0908(13) Uani 1 1 d . . . H23 H 0.5476 0.5044 0.9715 0.109 Uiso 1 1 calc R . . C24 C 0.3747(4) 0.6095(3) 0.95525(17) 0.0736(8) Uani 1 1 d . . . H24 H 0.3700 0.6387 0.9948 0.088 Uiso 1 1 calc R . . C25 C 0.2746(3) 0.6457(2) 0.90922(13) 0.0548(6) Uani 1 1 d . . . C26 C 0.1513(3) 0.72814(19) 0.91395(11) 0.0520(5) Uani 1 1 d . . . C27 C 0.5198(5) 1.1700(3) 0.85382(19) 0.0856(10) Uani 1 1 d . . . H27B H 0.6062 1.1407 0.8770 0.128 Uiso 1 1 calc R . . H27C H 0.4788 1.2326 0.8747 0.128 Uiso 1 1 calc R . . H27A H 0.5556 1.1905 0.8134 0.128 Uiso 1 1 calc R . . H5 H -0.144(3) 0.711(2) 0.8984(13) 0.050(7) 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 0.1326(4) 0.06004(18) 0.0949(3) 0.02620(16) -0.0005(3) 0.0058(2) O1 0.0753(13) 0.0703(13) 0.0944(15) 0.0126(11) -0.0242(12) 0.0090(11) O2 0.0799(13) 0.0831(13) 0.0480(9) -0.0144(9) 0.0075(9) -0.0081(12) O3 0.0842(14) 0.0748(11) 0.0560(9) -0.0224(9) 0.0024(10) 0.0029(13) C1 0.0567(13) 0.0497(12) 0.0518(12) 0.0038(10) 0.0084(11) 0.0029(11) C2 0.0653(15) 0.0513(12) 0.0669(14) 0.0151(11) 0.0003(14) 0.0051(14) C3 0.0577(14) 0.0614(14) 0.0583(13) 0.0071(12) -0.0014(12) 0.0070(14) C4 0.0556(14) 0.0589(14) 0.0678(15) 0.0117(12) -0.0063(12) -0.0014(13) C5 0.0538(12) 0.0497(11) 0.0482(11) 0.0031(9) 0.0046(11) 0.0062(12) C6 0.0509(12) 0.0469(12) 0.0465(11) -0.0016(9) 0.0018(10) 0.0046(10) C7 0.0609(14) 0.0489(12) 0.0568(13) 0.0067(10) 0.0041(12) 0.0008(12) C8 0.0648(15) 0.0565(13) 0.0699(15) -0.0003(11) 0.0017(15) 0.0089(14) C9 0.085(2) 0.0523(15) 0.0712(17) -0.0001(12) -0.0045(17) -0.0022(15) C10 0.0796(18) 0.0591(13) 0.0524(12) 0.0060(10) 0.0000(14) -0.0145(15) C11 0.0595(16) 0.0729(18) 0.092(2) -0.0017(16) 0.0167(17) -0.0045(15) C12 0.0667(18) 0.0543(15) 0.098(2) -0.0020(14) 0.0196(17) -0.0001(14) C13 0.0458(11) 0.0523(11) 0.0481(11) 0.0037(9) 0.0026(10) 0.0029(11) C14 0.0617(14) 0.0577(13) 0.0458(10) 0.0038(9) 0.0036(12) 0.0027(13) C15 0.0691(16) 0.0546(12) 0.0618(13) -0.0002(11) 0.0037(14) 0.0070(13) C16 0.0696(16) 0.0557(13) 0.0632(14) 0.0178(11) -0.0005(15) 0.0077(14) C17 0.0894(19) 0.0667(15) 0.0489(12) 0.0117(11) 0.0014(16) 0.0041(17) C18 0.0720(16) 0.0588(12) 0.0488(11) 0.0007(9) 0.0058(13) 0.0031(15) C19 0.0518(12) 0.0491(11) 0.0494(12) -0.0087(9) 0.0057(10) -0.0058(10) C20 0.0427(11) 0.0446(12) 0.0726(15) -0.0090(11) 0.0052(12) -0.0068(10) C21 0.0488(14) 0.0485(13) 0.126(3) -0.0196(15) 0.0138(18) -0.0036(13) C22 0.0408(14) 0.0464(15) 0.197(5) 0.012(2) 0.004(2) 0.0065(13) C23 0.0578(17) 0.0704(19) 0.144(4) 0.024(2) -0.030(2) -0.0070(17) C24 0.0599(16) 0.0721(17) 0.089(2) 0.0092(15) -0.0218(16) -0.0088(16) C25 0.0479(12) 0.0490(12) 0.0674(15) -0.0044(11) -0.0077(12) -0.0050(11) C26 0.0590(14) 0.0498(12) 0.0472(11) -0.0058(9) 0.0026(11) -0.0035(11) C27 0.096(2) 0.078(2) 0.083(2) 0.0027(17) -0.0042(19) -0.026(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 C16 1.894(2) . ? O1 C3 1.213(4) . ? O2 C19 1.215(3) . ? O3 C26 1.206(3) . ? C1 C2 1.344(4) . ? C1 C7 1.472(4) . ? C1 C6 1.523(3) . ? C2 C3 1.454(5) . ? C3 C4 1.497(4) . ? C4 C5 1.533(4) . ? C5 C13 1.528(3) . ? C5 C6 1.557(4) . ? C6 C26 1.540(3) . ? C6 C19 1.542(3) . ? C7 C12 1.379(4) . ? C7 C8 1.395(4) . ? C8 C9 1.384(5) . ? C9 C10 1.364(5) . ? C10 C11 1.384(4) . ? C10 C27 1.511(5) . ? C11 C12 1.380(5) . ? C13 C14 1.385(4) . ? C13 C18 1.389(3) . ? C14 C15 1.384(4) . ? C15 C16 1.376(4) . ? C16 C17 1.381(4) . ? C17 C18 1.382(4) . ? C19 C20 1.474(4) . ? C20 C21 1.389(4) . ? C20 C25 1.393(4) . ? C21 C22 1.383(6) . ? C22 C23 1.404(7) . ? C23 C24 1.357(6) . ? C24 C25 1.384(4) . ? C25 C26 1.463(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 C2 C1 C7 120.6(2) . . ? C2 C1 C6 120.4(2) . . ? C7 C1 C6 119.0(2) . . ? C1 C2 C3 124.3(2) . . ? O1 C3 C2 121.7(3) . . ? O1 C3 C4 120.6(3) . . ? C2 C3 C4 117.7(2) . . ? C3 C4 C5 111.5(2) . . ? C13 C5 C4 111.3(2) . . ? C13 C5 C6 115.5(2) . . ? C4 C5 C6 110.6(2) . . ? C1 C6 C26 112.8(2) . . ? C1 C6 C19 113.6(2) . . ? C26 C6 C19 102.8(2) . . ? C1 C6 C5 110.4(2) . . ? C26 C6 C5 107.27(19) . . ? C19 C6 C5 109.67(19) . . ? C12 C7 C8 116.8(3) . . ? C12 C7 C1 122.5(3) . . ? C8 C7 C1 120.6(3) . . ? C9 C8 C7 121.0(3) . . ? C10 C9 C8 121.9(3) . . ? C9 C10 C11 117.2(3) . . ? C9 C10 C27 122.3(3) . . ? C11 C10 C27 120.5(3) . . ? C12 C11 C10 121.6(3) . . ? C7 C12 C11 121.4(3) . . ? C14 C13 C18 118.5(2) . . ? C14 C13 C5 122.0(2) . . ? C18 C13 C5 119.5(2) . . ? C15 C14 C13 121.0(2) . . ? C16 C15 C14 119.1(3) . . ? C15 C16 C17 121.3(2) . . ? C15 C16 Br1 120.2(2) . . ? C17 C16 Br1 118.5(2) . . ? C16 C17 C18 118.8(2) . . ? C17 C18 C13 121.3(3) . . ? O2 C19 C20 127.1(2) . . ? O2 C19 C6 125.4(3) . . ? C20 C19 C6 107.5(2) . . ? C21 C20 C25 120.0(3) . . ? C21 C20 C19 129.7(3) . . ? C25 C20 C19 110.3(2) . . ? C22 C21 C20 117.4(4) . . ? C21 C22 C23 122.0(3) . . ? C24 C23 C22 120.2(4) . . ? C23 C24 C25 118.4(4) . . ? C24 C25 C20 122.0(3) . . ? C24 C25 C26 127.9(3) . . ? C20 C25 C26 110.2(2) . . ? O3 C26 C25 126.8(3) . . ? O3 C26 C6 125.0(3) . . ? C25 C26 C6 108.1(2) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 73.11 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.331 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.037