Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'J. Clayden' 'Thomas Adler' 'Josep Bonjoch' 'Mark Pickworth' 'Daniel Sole' 'Lluis Vallverdu' _publ_contact_author_name 'Prof J Clayden' _publ_contact_author_address ; School of Chemistry University of Manchester Oxford Road MANCHESTER M13 9PL UNITED KINGDOM ; _publ_contact_author_email J.P.CLAYDEN@MAN.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Slow interconversion of enantiomeric conformers or atropisomers of anilide and urea derivatives of 2-substituted anilines ; data_sohm132 _database_code_depnum_ccdc_archive 'CCDC 273163' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H18 I N O3' _chemical_formula_weight 375.19 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' 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' I I -0.4742 1.8119 '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, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.1130(10) _cell_length_b 12.4610(10) _cell_length_c 8.5280(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1499.8(2) _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 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 2.139 _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 0.71069 _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 7317 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 31.57 _reflns_number_total 4250 _reflns_number_gt 3813 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0252P)^2^+2.5079P] 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 0.0089(8) _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 0.00(6) _refine_ls_number_reflns 4250 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0945 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.015 _refine_ls_shift/su_mean 0.002 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 I1 I 1.07602(2) 0.33158(2) 0.76441(4) 0.04897(11) Uani 1 1 d . . . O1 O 0.9870(2) 0.2608(2) 0.2655(4) 0.0451(7) Uani 1 1 d . . . O2 O 0.9260(3) 0.0572(2) 0.3180(4) 0.0460(7) Uani 1 1 d . . . O3 O 0.7862(3) 0.1381(3) 0.3049(5) 0.0579(9) Uani 1 1 d . . . N N 0.9168(2) 0.3183(2) 0.4869(3) 0.0309(6) Uani 1 1 d . . . C1 C 0.9300(3) 0.2995(3) 0.7718(4) 0.0366(7) Uani 1 1 d . . . C2 C 0.8882(4) 0.2826(4) 0.9166(5) 0.0454(11) Uani 1 1 d . . . H2 H 0.9246 0.2847 1.0075 0.054 Uiso 1 1 calc R . . C3 C 0.7923(4) 0.2626(4) 0.9248(6) 0.0522(13) Uani 1 1 d . . . H3 H 0.7639 0.2515 1.0219 0.063 Uiso 1 1 calc R . . C4 C 0.7385(3) 0.2590(3) 0.7921(6) 0.0440(10) Uani 1 1 d . . . H4 H 0.6737 0.2463 0.7985 0.053 Uiso 1 1 calc R . . C5 C 0.7811(3) 0.2743(3) 0.6481(5) 0.0362(8) Uani 1 1 d . . . H5 H 0.7446 0.2699 0.5576 0.043 Uiso 1 1 calc R . . C6 C 0.8761(3) 0.2960(3) 0.6358(4) 0.0310(7) Uani 1 1 d . . . C7 C 0.9522(3) 0.2405(3) 0.3933(5) 0.0334(8) Uani 1 1 d . . . C8 C 0.9507(3) 0.1246(3) 0.4491(5) 0.0397(9) Uani 1 1 d . . . H8 H 0.9049 0.1156 0.5344 0.048 Uiso 1 1 calc R . . C9 C 1.0471(4) 0.0857(4) 0.4989(7) 0.0533(12) Uani 1 1 d . . . H9 H 1.0427 0.0125 0.5330 0.064 Uiso 1 1 calc R . . H9A H 1.0700 0.1294 0.5835 0.064 Uiso 1 1 calc R . . H9B H 1.0901 0.0904 0.4119 0.064 Uiso 1 1 calc R . . C10 C 0.8409(3) 0.0725(3) 0.2562(6) 0.0444(9) Uani 1 1 d . . . C11 C 0.8244(5) 0.0011(5) 0.1198(7) 0.0644(15) Uani 1 1 d . . . H11 H 0.8787 -0.0441 0.1046 0.077 Uiso 1 1 calc R . . H11A H 0.8142 0.0438 0.0277 0.077 Uiso 1 1 calc R . . H11B H 0.7696 -0.0426 0.1390 0.077 Uiso 1 1 calc R . . C12 C 0.9042(3) 0.4269(3) 0.4185(5) 0.0395(9) Uani 1 1 d . . . H12 H 0.9549 0.4374 0.3415 0.047 Uiso 1 1 calc R . . C13 C 0.9123(4) 0.5163(4) 0.5373(6) 0.0546(12) Uani 1 1 d . . . H13 H 0.9718 0.5105 0.5914 0.066 Uiso 1 1 calc R . . H13A H 0.8614 0.5109 0.6115 0.066 Uiso 1 1 calc R . . H13B H 0.9090 0.5843 0.4847 0.066 Uiso 1 1 calc R . . C14 C 0.8111(4) 0.4339(4) 0.3313(7) 0.0602(15) Uani 1 1 d . . . H14 H 0.8073 0.3765 0.2564 0.072 Uiso 1 1 calc R . . H14A H 0.8073 0.5015 0.2776 0.072 Uiso 1 1 calc R . . H14B H 0.7597 0.4281 0.4044 0.072 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 I1 0.03614(16) 0.06299(18) 0.04776(17) 0.00186(14) -0.00933(12) -0.00241(12) O1 0.0511(18) 0.0553(16) 0.0290(14) 0.0022(14) 0.0120(14) 0.0045(12) O2 0.0422(18) 0.0445(15) 0.0514(17) -0.0134(12) -0.0023(16) 0.0069(14) O3 0.040(2) 0.074(2) 0.059(2) -0.0145(17) -0.0014(15) 0.0074(16) N 0.0308(16) 0.0359(14) 0.0261(13) 0.0020(11) 0.0028(11) 0.0019(13) C1 0.0314(19) 0.0471(17) 0.0314(17) 0.0024(13) -0.0037(17) -0.0056(14) C2 0.048(3) 0.058(3) 0.030(2) 0.0056(18) -0.0024(17) -0.003(2) C3 0.059(3) 0.057(3) 0.040(3) 0.002(2) 0.021(2) -0.004(2) C4 0.034(2) 0.045(2) 0.053(3) 0.0002(18) 0.0139(19) -0.0026(16) C5 0.028(2) 0.043(2) 0.038(2) -0.0023(16) 0.0015(15) 0.0001(15) C6 0.034(2) 0.0321(17) 0.0268(18) -0.0003(13) 0.0039(14) 0.0009(14) C7 0.029(2) 0.042(2) 0.0287(18) 0.0027(15) 0.0008(13) 0.0017(14) C8 0.045(3) 0.0374(19) 0.037(2) -0.0022(16) 0.0051(16) 0.0052(16) C9 0.054(3) 0.051(3) 0.055(3) 0.001(2) -0.011(2) 0.013(2) C10 0.042(2) 0.0444(19) 0.047(3) -0.003(2) -0.001(2) -0.0071(15) C11 0.066(4) 0.060(3) 0.067(4) -0.019(3) -0.011(3) -0.005(3) C12 0.039(3) 0.0382(19) 0.041(2) 0.0075(16) 0.0007(17) 0.0024(15) C13 0.067(4) 0.039(2) 0.057(3) -0.0012(19) -0.010(3) 0.003(2) C14 0.059(4) 0.053(3) 0.069(4) 0.018(2) -0.017(3) 0.004(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 I1 C1 2.101(4) . ? O1 C7 1.222(5) . ? O2 C10 1.326(6) . ? O2 C8 1.441(5) . ? O3 C10 1.199(5) . ? N C7 1.351(5) . ? N C6 1.421(5) . ? N C12 1.485(5) . ? C1 C2 1.384(6) . ? C1 C6 1.387(5) . ? C2 C3 1.379(8) . ? C2 H2 0.9300 . ? C3 C4 1.364(8) . ? C3 H3 0.9300 . ? C4 C5 1.380(6) . ? C4 H4 0.9300 . ? C5 C6 1.372(6) . ? C5 H5 0.9300 . ? C7 C8 1.521(6) . ? C8 C9 1.505(7) . ? C8 H8 0.9800 . ? C9 H9 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C10 C11 1.483(7) . ? C11 H11 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C12 C13 1.510(6) . ? C12 C14 1.512(7) . ? C12 H12 0.9800 . ? C13 H13 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C14 H14 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? 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 C10 O2 C8 116.4(3) . . ? C7 N C6 122.5(3) . . ? C7 N C12 117.8(3) . . ? C6 N C12 118.7(3) . . ? C2 C1 C6 120.5(4) . . ? C2 C1 I1 118.2(3) . . ? C6 C1 I1 121.2(3) . . ? C3 C2 C1 119.4(5) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C4 C3 C2 120.7(4) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 121.4(4) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 118.5(4) . . ? C5 C6 N 120.1(4) . . ? C1 C6 N 121.3(4) . . ? O1 C7 N 121.8(4) . . ? O1 C7 C8 118.8(4) . . ? N C7 C8 119.4(3) . . ? O2 C8 C9 104.5(4) . . ? O2 C8 C7 108.3(3) . . ? C9 C8 C7 112.4(4) . . ? O2 C8 H8 110.5 . . ? C9 C8 H8 110.5 . . ? C7 C8 H8 110.5 . . ? C8 C9 H9 109.5 . . ? C8 C9 H9A 109.5 . . ? H9 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? O3 C10 O2 122.9(4) . . ? O3 C10 C11 125.5(5) . . ? O2 C10 C11 111.6(4) . . ? C10 C11 H11 109.5 . . ? C10 C11 H11A 109.5 . . ? H11 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N C12 C13 113.6(4) . . ? N C12 C14 110.5(4) . . ? C13 C12 C14 110.7(4) . . ? N C12 H12 107.2 . . ? C13 C12 H12 107.2 . . ? C14 C12 H12 107.2 . . ? C12 C13 H13 109.5 . . ? C12 C13 H13A 109.5 . . ? H13 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C14 H14 109.5 . . ? C12 C14 H14A 109.5 . . ? H14 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 31.57 _diffrn_measured_fraction_theta_full 0.888 _refine_diff_density_max 0.596 _refine_diff_density_min -1.019 _refine_diff_density_rms 0.094