# Electronic Supplementary Material (ESI) for Chemical Science # 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_toste70 #TrackingRef 'cmpd2b.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; toste70 ; _chemical_name_common toste70 _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 Br N2 O4 S' _chemical_formula_weight 389.26 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' N N 0.0311 0.0180 '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' S S 0.3331 0.5567 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' _diffrn_refln_scan_width 1.0 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.6678(10) _cell_length_b 13.5683(18) _cell_length_c 14.958(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1556.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9675 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 68.25 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.661 _exptl_crystal_F_000 792 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.120 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 5.038 _shelx_estimated_absorpt_T_min 0.583 _shelx_estimated_absorpt_T_max 0.633 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.669 _exptl_absorpt_correction_T_max 0.753 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source 'microfocus rotating anode' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.366 _diffrn_reflns_number 33759 _diffrn_reflns_av_unetI/netI 0.0103 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.399 _diffrn_reflns_theta_max 68.291 _diffrn_reflns_theta_full 67.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_point_group_measured_fraction_full 0.998 _reflns_number_total 2848 _reflns_number_gt 2847 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.719 _reflns_Friedel_fraction_max 0.995 _reflns_Friedel_fraction_full 0.997 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _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. ; _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SUPERFLIP _computing_structure_refinement SHELXL-2012 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0143P)^2^+0.9672P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary 'charge flipping' _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00218(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details ; Flack x determined using 1191 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.007(4) _chemical_absolute_configuration ad _refine_ls_number_reflns 2848 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0159 _refine_ls_R_factor_gt 0.0159 _refine_ls_wR_factor_ref 0.0411 _refine_ls_wR_factor_gt 0.0411 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _refine_ls_shift/su_max 0.001 _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_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 C1 C 0.2069(3) 1.24566(18) 0.18730(16) 0.0118(5) Uani 1 1 d . . . . . C2 C 0.3838(4) 1.25265(19) 0.16689(17) 0.0137(5) Uani 1 1 d . . . . . H2 H 0.4220 1.2506 0.1065 0.016 Uiso 1 1 calc R U . . . C3 C 0.5031(4) 1.26268(18) 0.23566(17) 0.0142(5) Uani 1 1 d . . . . . H3 H 0.6246 1.2664 0.2237 0.017 Uiso 1 1 calc R U . . . C4 C 0.4408(3) 1.26714(19) 0.32248(17) 0.0142(5) Uani 1 1 d . . . . . C5 C 0.2649(4) 1.26124(17) 0.34395(15) 0.0149(5) Uani 1 1 d . . . . . H5 H 0.2270 1.2649 0.4043 0.018 Uiso 1 1 calc R U . . . C6 C 0.1468(3) 1.24986(18) 0.27522(19) 0.0145(5) Uani 1 1 d . . . . . H6 H 0.0256 1.2449 0.2876 0.017 Uiso 1 1 calc R U . . . C7 C 0.2021(4) 1.08184(18) -0.00135(17) 0.0151(5) Uani 1 1 d . . . . . H7A H 0.3124 1.0608 0.0273 0.018 Uiso 1 1 calc R U . . . H7B H 0.2273 1.1333 -0.0465 0.018 Uiso 1 1 calc R U . . . C8 C 0.1047(4) 0.9947(2) -0.04227(17) 0.0200(6) Uani 1 1 d . . . . . H8A H 0.1869 0.9472 -0.0696 0.024 Uiso 1 1 calc R U . . . H8B H 0.0211 1.0171 -0.0884 0.024 Uiso 1 1 calc R U . . . C9 C 0.0091(4) 0.9482(2) 0.03696(18) 0.0175(6) Uani 1 1 d . . . . . H9A H 0.0852 0.9004 0.0681 0.021 Uiso 1 1 calc R U . . . H9B H -0.0976 0.9137 0.0166 0.021 Uiso 1 1 calc R U . . . C10 C -0.0381(3) 1.03502(18) 0.09950(16) 0.0121(5) Uani 1 1 d . . . . . H10 H -0.1631 1.0531 0.0899 0.015 Uiso 1 1 calc R U . . . C11 C -0.0090(3) 1.01563(19) 0.19761(16) 0.0120(5) Uani 1 1 d . . . . . C12 C -0.1262(3) 1.01694(19) 0.26286(17) 0.0137(5) Uani 1 1 d . . . . . C13 C -0.3180(3) 1.0333(2) 0.24417(18) 0.0172(6) Uani 1 1 d . . . . . H13A H -0.3324 1.0597 0.1836 0.026 Uiso 1 1 calc R U . . . H13B H -0.3654 1.0803 0.2876 0.026 Uiso 1 1 calc R U . . . H13C H -0.3805 0.9706 0.2492 0.026 Uiso 1 1 calc R U . . . C14 C -0.0859(4) 1.0024(2) 0.35989(17) 0.0199(5) Uani 1 1 d . . . . . H14A H 0.0270 0.9693 0.3660 0.030 Uiso 1 1 calc R U . . . H14B H -0.1770 0.9617 0.3873 0.030 Uiso 1 1 calc R U . . . H14C H -0.0814 1.0665 0.3899 0.030 Uiso 1 1 calc R U . . . N1 N 0.5682(3) 1.27706(17) 0.39613(16) 0.0196(5) Uani 1 1 d . . . . . N2 N 0.0739(3) 1.11589(15) 0.06504(14) 0.0129(4) Uani 1 1 d . . . . . O1 O 0.5170(3) 1.31280(19) 0.46632(14) 0.0339(5) Uani 1 1 d . . . . . O2 O 0.7174(3) 1.24799(15) 0.38310(13) 0.0258(4) Uani 1 1 d . . . . . O3 O -0.1150(2) 1.23881(14) 0.13646(12) 0.0171(4) Uani 1 1 d . . . . . O4 O 0.1116(3) 1.29064(13) 0.02679(12) 0.0169(4) Uani 1 1 d . . . . . S1 S 0.05534(8) 1.22804(4) 0.09839(4) 0.01208(14) Uani 1 1 d . . . . . Br1 Br 0.23181(3) 0.98868(2) 0.22451(2) 0.01707(9) 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 C1 0.0152(12) 0.0108(11) 0.0092(11) 0.0003(8) -0.0019(10) 0.0015(10) C2 0.0180(13) 0.0111(12) 0.0118(12) 0.0002(9) 0.0022(11) 0.0003(10) C3 0.0140(11) 0.0122(11) 0.0163(13) 0.0001(10) -0.0004(12) 0.0008(9) C4 0.0177(13) 0.0111(12) 0.0137(12) 0.0007(10) -0.0040(10) 0.0000(10) C5 0.0224(14) 0.0148(11) 0.0076(10) 0.0002(9) 0.0031(11) 0.0032(12) C6 0.0125(11) 0.0147(11) 0.0162(12) -0.0017(11) 0.0012(11) 0.0031(9) C7 0.0153(12) 0.0165(12) 0.0136(11) -0.0024(10) 0.0048(11) -0.0011(10) C8 0.0262(13) 0.0207(14) 0.0132(12) -0.0050(11) 0.0036(10) -0.0066(12) C9 0.0206(13) 0.0180(13) 0.0139(13) -0.0024(10) 0.0001(11) -0.0047(11) C10 0.0102(11) 0.0145(12) 0.0116(12) 0.0015(10) -0.0007(9) -0.0039(9) C11 0.0102(10) 0.0130(11) 0.0130(12) 0.0017(10) -0.0041(8) -0.0004(10) C12 0.0173(11) 0.0103(10) 0.0137(12) 0.0006(10) -0.0002(9) -0.0010(10) C13 0.0158(12) 0.0180(13) 0.0177(13) 0.0017(10) 0.0040(10) -0.0006(9) C14 0.0258(13) 0.0222(14) 0.0117(12) 0.0028(11) 0.0018(10) -0.0010(12) N1 0.0243(13) 0.0184(11) 0.0162(12) 0.0017(9) -0.0056(10) -0.0038(10) N2 0.0144(10) 0.0136(10) 0.0106(10) -0.0001(8) 0.0023(9) 0.0001(8) O1 0.0351(12) 0.0525(14) 0.0141(10) -0.0103(10) -0.0061(9) 0.0011(11) O2 0.0196(10) 0.0289(10) 0.0289(10) -0.0014(8) -0.0109(9) 0.0026(9) O3 0.0141(9) 0.0220(9) 0.0154(9) -0.0009(7) -0.0025(8) 0.0050(8) O4 0.0255(10) 0.0153(9) 0.0100(8) 0.0021(7) -0.0028(8) -0.0002(8) S1 0.0146(3) 0.0131(3) 0.0086(3) 0.0004(2) -0.0019(2) 0.0019(2) Br1 0.01371(13) 0.02172(14) 0.01579(13) 0.00084(10) -0.00363(9) 0.00289(10) _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 C1 C2 1.393(4) . ? C1 C6 1.395(4) . ? C1 S1 1.782(3) . ? C2 C3 1.383(4) . ? C2 H2 0.9500 . ? C3 C4 1.385(4) . ? C3 H3 0.9500 . ? C4 C5 1.389(4) . ? C4 N1 1.479(3) . ? C5 C6 1.379(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N2 1.472(3) . ? C7 C8 1.527(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.529(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.547(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 N2 1.485(3) . ? C10 C11 1.508(3) . ? C10 H10 1.0000 . ? C11 C12 1.327(3) . ? C11 Br1 1.925(2) . ? C12 C14 1.497(4) . ? C12 C13 1.513(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? N1 O1 1.221(3) . ? N1 O2 1.226(3) . ? N2 S1 1.608(2) . ? O3 S1 1.4324(19) . ? O4 S1 1.4334(19) . ? 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 C6 121.7(2) . . ? C2 C1 S1 118.70(19) . . ? C6 C1 S1 119.58(19) . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 118.2(3) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C3 C4 C5 123.3(2) . . ? C3 C4 N1 118.3(2) . . ? C5 C4 N1 118.3(2) . . ? C6 C5 C4 118.2(2) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C5 C6 C1 119.4(2) . . ? C5 C6 H6 120.3 . . ? C1 C6 H6 120.3 . . ? N2 C7 C8 100.7(2) . . ? N2 C7 H7A 111.6 . . ? C8 C7 H7A 111.6 . . ? N2 C7 H7B 111.6 . . ? C8 C7 H7B 111.6 . . ? H7A C7 H7B 109.4 . . ? C7 C8 C9 104.1(2) . . ? C7 C8 H8A 110.9 . . ? C9 C8 H8A 110.9 . . ? C7 C8 H8B 110.9 . . ? C9 C8 H8B 110.9 . . ? H8A C8 H8B 109.0 . . ? C8 C9 C10 105.5(2) . . ? C8 C9 H9A 110.6 . . ? C10 C9 H9A 110.6 . . ? C8 C9 H9B 110.6 . . ? C10 C9 H9B 110.6 . . ? H9A C9 H9B 108.8 . . ? N2 C10 C11 112.4(2) . . ? N2 C10 C9 102.56(19) . . ? C11 C10 C9 114.9(2) . . ? N2 C10 H10 108.9 . . ? C11 C10 H10 108.9 . . ? C9 C10 H10 108.9 . . ? C12 C11 C10 127.8(2) . . ? C12 C11 Br1 119.91(18) . . ? C10 C11 Br1 112.24(16) . . ? C11 C12 C14 124.8(2) . . ? C11 C12 C13 121.6(2) . . ? C14 C12 C13 113.5(2) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O1 N1 O2 124.4(2) . . ? O1 N1 C4 117.7(2) . . ? O2 N1 C4 118.0(2) . . ? C7 N2 C10 112.86(19) . . ? C7 N2 S1 124.43(18) . . ? C10 N2 S1 122.71(17) . . ? O3 S1 O4 120.74(12) . . ? O3 S1 N2 107.49(12) . . ? O4 S1 N2 107.60(11) . . ? O3 S1 C1 106.52(12) . . ? O4 S1 C1 106.36(11) . . ? N2 S1 C1 107.51(12) . . ? _refine_diff_density_max 0.270 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.046 _shelxl_version_number 2012-9 _shelx_res_file ; TITL toste70_0m CELL 1.54178 7.6678 13.5683 14.9584 90.000 90.000 90.000 ZERR 4.00 0.0010 0.0018 0.0020 0.000 0.000 0.000 LATT -1 SYMM 1/2 - X, - Y, 1/2 + Z SYMM - X, 1/2 + Y, 1/2 - Z SYMM 1/2 + X, 1/2 - Y, - Z SFAC C H N O S BR UNIT 56 68 8 16 4 4 MERG 2 FMAP 2 PLAN 10 SIZE 0.10 0.10 0.12 ACTA 134.00 BOND $H LIST 4 WPDB -2 L.S. 8 TEMP -173.00 WGHT 0.014300 0.967200 EXTI 0.002183 FVAR 0.10342 C1 1 0.206904 1.245656 0.187301 11.00000 0.01524 0.01083 = 0.00921 0.00030 -0.00186 0.00147 C2 1 0.383785 1.252651 0.166888 11.00000 0.01805 0.01112 = 0.01179 0.00024 0.00218 0.00026 AFIX 43 H2 2 0.421960 1.250559 0.106498 11.00000 -1.20000 AFIX 0 C3 1 0.503103 1.262681 0.235658 11.00000 0.01402 0.01220 = 0.01626 0.00008 -0.00037 0.00084 AFIX 43 H3 2 0.624587 1.266410 0.223658 11.00000 -1.20000 AFIX 0 C4 1 0.440757 1.267142 0.322484 11.00000 0.01771 0.01112 = 0.01371 0.00066 -0.00398 0.00002 C5 1 0.264875 1.261239 0.343948 11.00000 0.02237 0.01481 = 0.00764 0.00017 0.00314 0.00325 AFIX 43 H5 2 0.226970 1.264941 0.404319 11.00000 -1.20000 AFIX 0 C6 1 0.146795 1.249856 0.275222 11.00000 0.01248 0.01465 = 0.01624 -0.00174 0.00120 0.00306 AFIX 43 H6 2 0.025604 1.244917 0.287633 11.00000 -1.20000 AFIX 0 C7 1 0.202140 1.081843 -0.001355 11.00000 0.01533 0.01653 = 0.01357 -0.00238 0.00477 -0.00108 AFIX 23 H7A 2 0.312392 1.060829 0.027331 11.00000 -1.20000 H7B 2 0.227272 1.133311 -0.046463 11.00000 -1.20000 AFIX 0 C8 1 0.104657 0.994655 -0.042269 11.00000 0.02621 0.02074 = 0.01318 -0.00500 0.00361 -0.00656 AFIX 23 H8A 2 0.186949 0.947183 -0.069594 11.00000 -1.20000 H8B 2 0.021126 1.017138 -0.088430 11.00000 -1.20000 AFIX 0 C9 1 0.009078 0.948228 0.036965 11.00000 0.02057 0.01800 = 0.01390 -0.00239 0.00008 -0.00470 AFIX 23 H9A 2 0.085227 0.900361 0.068132 11.00000 -1.20000 H9B 2 -0.097568 0.913740 0.016640 11.00000 -1.20000 AFIX 0 C10 1 -0.038065 1.035025 0.099495 11.00000 0.01024 0.01450 = 0.01165 0.00155 -0.00071 -0.00393 AFIX 13 H10 2 -0.163133 1.053053 0.089924 11.00000 -1.20000 AFIX 0 C11 1 -0.009011 1.015628 0.197609 11.00000 0.01016 0.01298 = 0.01301 0.00170 -0.00409 -0.00039 C12 1 -0.126249 1.016945 0.262864 11.00000 0.01728 0.01029 = 0.01366 0.00059 -0.00017 -0.00102 C13 1 -0.318036 1.033332 0.244171 11.00000 0.01583 0.01802 = 0.01769 0.00173 0.00404 -0.00057 AFIX 137 H13A 2 -0.332359 1.059728 0.183631 11.00000 -1.50000 H13B 2 -0.365417 1.080313 0.287603 11.00000 -1.50000 H13C 2 -0.380526 0.970569 0.249174 11.00000 -1.50000 AFIX 0 C14 1 -0.085930 1.002363 0.359893 11.00000 0.02578 0.02223 = 0.01171 0.00282 0.00185 -0.00097 AFIX 137 H14A 2 0.027034 0.969254 0.365991 11.00000 -1.50000 H14B 2 -0.177043 0.961748 0.387345 11.00000 -1.50000 H14C 2 -0.081389 1.066541 0.389859 11.00000 -1.50000 AFIX 0 N1 3 0.568168 1.277059 0.396130 11.00000 0.02428 0.01842 = 0.01617 0.00173 -0.00559 -0.00381 N2 3 0.073871 1.115886 0.065035 11.00000 0.01443 0.01361 = 0.01056 -0.00010 0.00230 0.00010 O1 4 0.516952 1.312797 0.466316 11.00000 0.03514 0.05249 = 0.01405 -0.01031 -0.00606 0.00106 O2 4 0.717388 1.247985 0.383101 11.00000 0.01956 0.02892 = 0.02887 -0.00137 -0.01087 0.00257 O3 4 -0.115012 1.238807 0.136464 11.00000 0.01405 0.02196 = 0.01539 -0.00091 -0.00253 0.00497 O4 4 0.111630 1.290644 0.026795 11.00000 0.02546 0.01529 = 0.01000 0.00208 -0.00277 -0.00019 S1 5 0.055341 1.228044 0.098394 11.00000 0.01460 0.01307 = 0.00855 0.00036 -0.00185 0.00186 BR1 6 0.231815 0.988677 0.224513 11.00000 0.01371 0.02172 = 0.01579 0.00084 -0.00363 0.00289 HKLF 4 REM toste70_0m REM R1 = 0.0159 for 2847 Fo > 4sig(Fo) and 0.0159 for all 2848 data REM 202 parameters refined using 0 restraints END WGHT 0.0149 0.9732 REM Highest difference peak 0.270, deepest hole -0.252, 1-sigma level 0.046 Q1 1 0.0667 1.1679 0.0817 11.00000 0.05 0.27 Q2 1 0.1162 0.9856 0.2299 11.00000 0.05 0.23 Q3 1 0.2877 1.2583 0.1770 11.00000 0.05 0.22 Q4 1 -0.0174 0.9930 0.0646 11.00000 0.05 0.21 Q5 1 0.1294 1.2364 0.1475 11.00000 0.05 0.20 Q6 1 0.0250 1.0778 0.0828 11.00000 0.05 0.20 Q7 1 -0.1002 1.0034 0.3117 11.00000 0.05 0.20 Q8 1 -0.2232 1.0216 0.2486 11.00000 0.05 0.19 Q9 1 0.4562 1.2559 0.2776 11.00000 0.05 0.19 Q10 1 -0.0512 1.2257 0.1049 11.00000 0.05 0.18 ; _shelx_res_checksum 38547 _database_code_depnum_ccdc_archive 'CCDC 931059'