# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2021 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_testm1_tw _database_code_depnum_ccdc_archive 'CCDC 2061359' loop_ _audit_author_name _audit_author_address 'Hazel Sparkes' ;University of Bristol United Kingdom ; _audit_update_record ; 2021-02-05 deposited with the CCDC. 2021-06-22 downloaded from the CCDC. ; _audit_creation_date 2021-02-04 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C11 H8 Br F2 N O' _chemical_formula_sum 'C11 H8 Br F2 N O' _chemical_formula_weight 288.09 _chemical_melting_point ? 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3373(5) _cell_length_b 14.2535(9) _cell_length_c 9.9567(6) _cell_angle_alpha 90 _cell_angle_beta 90.050(4) _cell_angle_gamma 90 _cell_volume 1041.29(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 7253 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 27.85 _cell_measurement_theta_min 2.50 _shelx_estimated_absorpt_T_max 0.693 _shelx_estimated_absorpt_T_min 0.288 _exptl_absorpt_coefficient_mu 3.951 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0682 before and 0.0413 after correction. The Ratio of minimum to maximum transmission is 0.6915. The \l/2 correction factor is Not present. ; _exptl_absorpt_special_details ? _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_F_000 568 _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.1 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_av_unetI/netI 0.0201 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2506 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.053 _diffrn_reflns_theta_min 2.495 _diffrn_ambient_temperature 100(2) _diffrn_detector 'Bruker area detector' _diffrn_detector_area_resol_mean ? _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'Bruker Apex II kappa CCDC area detector' _diffrn_measurement_device_type 'Bruker Apex II kappa CCDC area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.35 _diffrn_source_voltage 45.0 _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2388 _reflns_number_total 2506 _reflns_special_details ; _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. Completness statistics refer to single and composite reflections containing twin component 1 only. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_collection ? _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _refine_diff_density_max 0.884 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.088 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.184 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 148 _refine_ls_number_reflns 2506 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0282 _refine_ls_restrained_S_all 1.184 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0257P)^2^+0.6028P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.0647 _refine_special_details 'Refined as a two component twin.' _olex2_refinement_description ; 1. Others Fixed Uiso: H8(0.015) H10(0.02) H11A(0.032) H11B(0.032) H11C(0.032) H4(0.022) H2(0.026) H3(0.027) Fixed X: H8(0.165539) H10(0.261852) H11A(0.239843) H11B(0.041484) H11C(0.079925) H4(0.220704) H2(0.365588) H3(0.305563) Fixed Y: H8(0.64567) H10(0.764662) H11A(0.448021) H11B(0.421484) H11C(0.524344) H4(0.312355) H2(0.324522) H3(0.238095) Fixed Z: H8(0.184564) H10(0.090833) H11A(0.353081) H11B(0.297967) H11C(0.355862) H4(0.146965) H2(-0.245749) H3(-0.051711) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.37412(6) 0.51475(2) -0.32876(5) 0.01927(8) Uani 1 1 d . . . . . F1 F 0.3560(3) 0.82961(12) -0.06868(18) 0.0247(4) Uani 1 1 d . . . . . F2 F 0.0682(3) 0.82180(15) -0.0184(2) 0.0322(5) Uani 1 1 d . . . . . O1 O 0.1856(4) 0.68917(17) -0.2032(2) 0.0238(6) Uani 1 1 d . . . . . N1 N 0.1850(3) 0.50352(16) 0.1707(3) 0.0144(5) Uani 1 1 d . . . . . C8 C 0.1885(4) 0.5927(2) 0.1291(3) 0.0124(6) Uani 1 1 d . . . . . H8 H 0.165539 0.645670 0.184564 0.015 Uiso 1 1 calc R U . . . C9 C 0.2153(4) 0.6828(2) -0.0830(3) 0.0148(6) Uani 1 1 d . . . . . C10 C 0.2296(4) 0.7753(2) -0.0056(3) 0.0170(6) Uani 1 1 d . . . . . H10 H 0.261852 0.764662 0.090833 0.020 Uiso 1 1 calc R U . . . C11 C 0.1322(6) 0.4717(2) 0.3057(3) 0.0215(8) Uani 1 1 d . . . . . H11A H 0.239843 0.448021 0.353081 0.032 Uiso 1 1 calc R U . . . H11B H 0.041484 0.421484 0.297967 0.032 Uiso 1 1 calc R U . . . H11C H 0.079925 0.524344 0.355862 0.032 Uiso 1 1 calc R U . . . C1 C 0.3131(4) 0.4525(2) -0.1663(3) 0.0158(5) Uani 1 1 d . . . . . C6 C 0.2595(4) 0.5007(2) -0.0511(3) 0.0126(6) Uani 1 1 d . . . . . C4 C 0.2443(4) 0.3474(2) 0.0677(3) 0.0186(6) Uani 1 1 d . . . . . H4 H 0.220704 0.312355 0.146965 0.022 Uiso 1 1 calc R U . . . C2 C 0.3298(4) 0.3561(2) -0.1660(4) 0.0216(6) Uani 1 1 d . . . . . H2 H 0.365588 0.324522 -0.245749 0.026 Uiso 1 1 calc R U . . . C5 C 0.2295(4) 0.4449(2) 0.0655(3) 0.0124(5) Uani 1 1 d . . . . . C7 C 0.2307(4) 0.5969(2) -0.0075(3) 0.0129(5) Uani 1 1 d . . . . . C3 C 0.2945(5) 0.3045(2) -0.0495(4) 0.0225(7) Uani 1 1 d . . . . . H3 H 0.305563 0.238095 -0.051711 0.027 Uiso 1 1 calc R U . . . 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 0.01992(13) 0.02329(14) 0.01460(12) -0.00015(14) 0.00310(18) 0.00503(15) F1 0.0322(12) 0.0195(9) 0.0224(9) 0.0005(7) 0.0065(9) -0.0099(9) F2 0.0262(11) 0.0212(10) 0.0494(14) -0.0098(10) 0.0068(10) -0.0001(8) O1 0.0436(15) 0.0163(11) 0.0115(10) -0.0001(8) 0.0003(9) 0.0017(9) N1 0.0168(11) 0.0146(12) 0.0117(10) 0.0022(11) 0.0004(10) -0.0037(8) C8 0.0119(13) 0.0140(14) 0.0114(12) 0.0005(10) -0.0016(10) -0.0029(10) C9 0.0178(16) 0.0141(15) 0.0126(13) -0.0006(11) 0.0024(12) 0.0009(11) C10 0.0247(16) 0.0130(14) 0.0132(13) 0.0006(11) 0.0035(12) -0.0021(12) C11 0.0273(15) 0.0195(15) 0.018(2) 0.0081(11) 0.0009(18) -0.0040(17) C1 0.0132(12) 0.0173(13) 0.0168(13) 0.0008(13) -0.0024(12) -0.0023(10) C6 0.0119(13) 0.0122(14) 0.0139(14) 0.0033(10) -0.0004(10) -0.0017(10) C4 0.0159(14) 0.0167(15) 0.0233(16) 0.0033(12) -0.0021(12) -0.0019(12) C2 0.0176(14) 0.0196(15) 0.0276(15) -0.0063(14) -0.0023(14) 0.0023(11) C5 0.0087(13) 0.0167(15) 0.0119(13) 0.0032(11) -0.0005(11) -0.0021(11) C7 0.0127(13) 0.0150(14) 0.0111(13) 0.0002(11) -0.0014(11) -0.0026(11) C3 0.0198(16) 0.0138(15) 0.0338(18) 0.0000(13) 0.0008(14) 0.0015(12) _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 1.899(3) . ? F1 C10 1.362(3) . ? F2 C10 1.363(4) . ? O1 C9 1.220(4) . ? N1 C8 1.338(4) . ? N1 C11 1.471(4) . ? N1 C5 1.378(4) . ? C8 H8 0.9500 . ? C8 C7 1.396(4) . ? C9 C10 1.531(4) . ? C9 C7 1.441(4) . ? C10 H10 1.0000 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C1 C6 1.394(4) . ? C1 C2 1.379(4) . ? C6 C5 1.424(4) . ? C6 C7 1.455(4) . ? C4 H4 0.9500 . ? C4 C5 1.395(4) . ? C4 C3 1.368(5) . ? C2 H2 0.9500 . ? C2 C3 1.399(5) . ? C3 H3 0.9500 . ? 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 N1 C11 125.5(3) . . ? C8 N1 C5 109.7(3) . . ? C5 N1 C11 124.7(2) . . ? N1 C8 H8 124.9 . . ? N1 C8 C7 110.3(3) . . ? C7 C8 H8 124.9 . . ? O1 C9 C10 116.2(3) . . ? O1 C9 C7 126.1(3) . . ? C7 C9 C10 117.6(3) . . ? F1 C10 F2 105.8(2) . . ? F1 C10 C9 107.7(2) . . ? F1 C10 H10 111.6 . . ? F2 C10 C9 108.2(3) . . ? F2 C10 H10 111.6 . . ? C9 C10 H10 111.6 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? N1 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C6 C1 Br1 122.5(2) . . ? C2 C1 Br1 116.5(3) . . ? C2 C1 C6 120.9(3) . . ? C1 C6 C5 116.1(3) . . ? C1 C6 C7 138.7(3) . . ? C5 C6 C7 105.1(2) . . ? C5 C4 H4 121.5 . . ? C3 C4 H4 121.5 . . ? C3 C4 C5 117.0(3) . . ? C1 C2 H2 119.7 . . ? C1 C2 C3 120.6(3) . . ? C3 C2 H2 119.7 . . ? N1 C5 C6 108.6(2) . . ? N1 C5 C4 127.6(3) . . ? C4 C5 C6 123.8(3) . . ? C8 C7 C9 121.8(3) . . ? C8 C7 C6 106.4(2) . . ? C9 C7 C6 131.1(3) . . ? C4 C3 C2 121.5(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? 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 Br1 C1 C6 C5 -176.1(2) . . . . ? Br1 C1 C6 C7 -0.1(5) . . . . ? Br1 C1 C2 C3 177.6(2) . . . . ? O1 C9 C10 F1 -53.5(4) . . . . ? O1 C9 C10 F2 60.4(4) . . . . ? O1 C9 C7 C8 -152.4(3) . . . . ? O1 C9 C7 C6 16.6(5) . . . . ? N1 C8 C7 C9 170.0(3) . . . . ? N1 C8 C7 C6 -1.4(3) . . . . ? C8 N1 C5 C6 -1.3(3) . . . . ? C8 N1 C5 C4 178.7(3) . . . . ? C10 C9 C7 C8 24.9(4) . . . . ? C10 C9 C7 C6 -166.0(3) . . . . ? C11 N1 C8 C7 -175.2(3) . . . . ? C11 N1 C5 C6 175.7(3) . . . . ? C11 N1 C5 C4 -4.3(5) . . . . ? C1 C6 C5 N1 177.6(2) . . . . ? C1 C6 C5 C4 -2.4(5) . . . . ? C1 C6 C7 C8 -175.6(4) . . . . ? C1 C6 C7 C9 14.1(6) . . . . ? C1 C2 C3 C4 -0.6(5) . . . . ? C6 C1 C2 C3 -0.5(5) . . . . ? C2 C1 C6 C5 1.9(4) . . . . ? C2 C1 C6 C7 177.9(3) . . . . ? C5 N1 C8 C7 1.7(3) . . . . ? C5 C6 C7 C8 0.6(3) . . . . ? C5 C6 C7 C9 -169.7(3) . . . . ? C5 C4 C3 C2 0.2(5) . . . . ? C7 C9 C10 F1 128.9(3) . . . . ? C7 C9 C10 F2 -117.2(3) . . . . ? C7 C6 C5 N1 0.3(3) . . . . ? C7 C6 C5 C4 -179.7(3) . . . . ? C3 C4 C5 N1 -178.6(3) . . . . ? C3 C4 C5 C6 1.4(5) . . . . ? _shelx_res_file ; TITL testm1 in P2(1)/c testm1_tw.res created by SHELXL-2018/3 at 16:03:58 on 11-Dec-2020 CELL 0.71073 7.3373 14.2535 9.9567 90 90.05 90 ZERR 4 0.0005 0.0009 0.0006 0 0.0043 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br F N O UNIT 44 32 4 8 4 4 L.S. 4 PLAN 5 SIZE 0.1 0.18 0.42 TEMP -173(2) CONF MORE -1 fmap 2 acta BOND $H REM REM REM WGHT 0.025700 0.602800 BASF 0.24124 0.48793 FVAR 13.73673 BR1 3 0.374123 0.514754 -0.328765 11.00000 0.01992 0.02329 = 0.01460 -0.00015 0.00310 0.00503 F1 4 0.355976 0.829607 -0.068682 11.00000 0.03215 0.01948 = 0.02241 0.00053 0.00650 -0.00991 F2 4 0.068179 0.821805 -0.018441 11.00000 0.02615 0.02116 = 0.04935 -0.00984 0.00685 -0.00008 O1 6 0.185641 0.689166 -0.203242 11.00000 0.04358 0.01626 = 0.01146 -0.00013 0.00032 0.00171 N1 5 0.185013 0.503524 0.170657 11.00000 0.01683 0.01464 = 0.01172 0.00223 0.00039 -0.00374 C8 1 0.188491 0.592747 0.129102 11.00000 0.01191 0.01404 = 0.01137 0.00048 -0.00161 -0.00290 AFIX 43 H8 2 0.165539 0.645670 0.184564 11.00000 -1.20000 AFIX 0 C9 1 0.215313 0.682788 -0.083006 11.00000 0.01779 0.01405 = 0.01258 -0.00057 0.00240 0.00089 C10 1 0.229625 0.775310 -0.005577 11.00000 0.02471 0.01296 = 0.01319 0.00059 0.00350 -0.00211 AFIX 13 H10 2 0.261852 0.764662 0.090833 11.00000 -1.20000 AFIX 0 C11 1 0.132155 0.471686 0.305658 11.00000 0.02734 0.01954 = 0.01763 0.00807 0.00088 -0.00401 AFIX 137 H11A 2 0.239843 0.448021 0.353081 11.00000 -1.50000 H11B 2 0.041484 0.421484 0.297967 11.00000 -1.50000 H11C 2 0.079925 0.524344 0.355862 11.00000 -1.50000 AFIX 0 C1 1 0.313081 0.452466 -0.166295 11.00000 0.01321 0.01732 = 0.01679 0.00084 -0.00237 -0.00227 C6 1 0.259461 0.500653 -0.051072 11.00000 0.01186 0.01216 = 0.01390 0.00329 -0.00044 -0.00165 C4 1 0.244328 0.347397 0.067707 11.00000 0.01587 0.01670 = 0.02332 0.00329 -0.00210 -0.00191 AFIX 43 H4 2 0.220704 0.312355 0.146965 11.00000 -1.20000 AFIX 0 C2 1 0.329773 0.356128 -0.166023 11.00000 0.01760 0.01957 = 0.02760 -0.00631 -0.00235 0.00226 AFIX 43 H2 2 0.365588 0.324522 -0.245749 11.00000 -1.20000 AFIX 0 C5 1 0.229462 0.444943 0.065524 11.00000 0.00872 0.01668 = 0.01193 0.00319 -0.00046 -0.00211 C7 1 0.230688 0.596944 -0.007469 11.00000 0.01265 0.01502 = 0.01114 0.00024 -0.00144 -0.00256 C3 1 0.294468 0.304481 -0.049458 11.00000 0.01984 0.01380 = 0.03376 0.00001 0.00085 0.00154 AFIX 43 H3 2 0.305563 0.238095 -0.051711 11.00000 -1.20000 AFIX 0 HKLF 5 REM testm1 in P2(1)/c REM wR2 = 0.0647, GooF = S = 1.184, Restrained GooF = 1.184 for all data REM R1 = 0.0282 for 2388 Fo > 4sig(Fo) and 0.0307 for all 2506 data REM 148 parameters refined using 0 restraints END WGHT 0.0257 0.6030 REM Highest difference peak 0.884, deepest hole -0.533, 1-sigma level 0.088 Q1 1 0.0304 0.4810 0.3446 11.00000 0.05 0.88 Q2 1 0.2642 0.5002 -0.3444 11.00000 0.05 0.77 Q3 1 0.4559 0.4840 -0.3506 11.00000 0.05 0.48 Q4 1 0.5189 0.5447 -0.3423 11.00000 0.05 0.45 Q5 1 0.0000 0.5000 0.0000 10.50000 0.05 0.43 ; _shelx_res_checksum 11297 _olex2_submission_special_instructions 'No special instructions were received' loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.271(18) 2 0.241(8) 3 0.488(16)