# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Maria Cid' _publ_contact_author_email belen.cid@uam.es loop_ _publ_author_name M.Cid S.Duce J.C.Ruano I.Alonso M.Jorge data_jg10551s _database_code_depnum_ccdc_archive 'CCDC 838553' #TrackingRef '- jg10551s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 I O' _chemical_formula_weight 312.13 _chemical_absolute_configuration ad 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' I I -0.4742 1.8119 '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, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.4376(7) _cell_length_b 9.7637(12) _cell_length_c 22.815(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1211.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4087 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 24.49 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.712 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.615 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5494 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker SMART1000 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9292 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2156 _reflns_number_gt 1821 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0129P)^2^+1.4004P] 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 0.00(3) _refine_ls_number_reflns 2156 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0640 _refine_ls_wR_factor_gt 0.0586 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I I -0.05793(9) 0.10136(4) 0.956886(16) 0.08742(15) Uani 1 1 d . . . O O -0.3370(6) 0.3187(3) 0.69197(14) 0.0622(9) Uani 1 1 d . . . C1 C -0.2019(9) 0.2572(4) 0.6592(2) 0.0498(11) Uani 1 1 d . . . C2 C -0.2448(10) 0.2600(5) 0.5961(2) 0.0638(13) Uani 1 1 d . . . H2 H -0.3623 0.3200 0.5813 0.077 Uiso 1 1 calc R . . C3 C -0.1242(9) 0.1813(5) 0.55908(19) 0.0640(14) Uani 1 1 d . . . H3 H -0.1599 0.1887 0.5193 0.077 Uiso 1 1 calc R . . C4 C 0.0644(10) 0.0820(5) 0.57761(18) 0.0631(12) Uani 1 1 d . . . H4A H 0.2256 0.1200 0.5694 0.076 Uiso 1 1 calc R . . H4B H 0.0465 -0.0008 0.5545 0.076 Uiso 1 1 calc R . . C5 C 0.0510(9) 0.0445(4) 0.64261(17) 0.0473(10) Uani 1 1 d . . . H5 H -0.0955 -0.0124 0.6483 0.057 Uiso 1 1 calc R . . C6 C 0.0190(7) 0.1753(4) 0.67969(17) 0.0422(9) Uani 1 1 d . . . H6 H 0.1639 0.2323 0.6722 0.051 Uiso 1 1 calc R . . C7 C 0.2718(8) -0.0390(5) 0.6609(2) 0.0562(12) Uani 1 1 d . . . H7A H 0.4182 0.0150 0.6563 0.084 Uiso 1 1 calc R . . H7B H 0.2830 -0.1193 0.6368 0.084 Uiso 1 1 calc R . . H7C H 0.2546 -0.0656 0.7012 0.084 Uiso 1 1 calc R . . C1' C 0.0128(7) 0.1497(4) 0.74508(19) 0.0406(9) Uani 1 1 d . . . C2' C 0.1901(8) 0.2012(4) 0.78198(19) 0.0450(10) Uani 1 1 d . . . H2' H 0.3222 0.2491 0.7661 0.054 Uiso 1 1 calc R . . C3' C 0.1770(9) 0.1837(4) 0.8420(2) 0.0509(11) Uani 1 1 d . . . H3' H 0.2992 0.2187 0.8663 0.061 Uiso 1 1 calc R . . C4' C -0.0198(8) 0.1138(4) 0.86534(17) 0.0472(10) Uani 1 1 d . . . C5' C -0.1959(8) 0.0569(4) 0.82973(19) 0.0482(10) Uani 1 1 d . . . H5' H -0.3244 0.0065 0.8458 0.058 Uiso 1 1 calc R . . C6' C -0.1803(8) 0.0755(4) 0.77001(19) 0.0479(10) Uani 1 1 d . . . H6' H -0.3004 0.0379 0.7458 0.057 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 I 0.1218(3) 0.0916(3) 0.04882(17) -0.00321(19) 0.0030(2) 0.0091(3) O 0.058(2) 0.059(2) 0.070(2) 0.0031(17) 0.0089(18) 0.0148(17) C1 0.049(3) 0.041(2) 0.059(3) 0.009(2) 0.001(2) -0.005(2) C2 0.067(3) 0.064(3) 0.060(3) 0.014(3) -0.003(3) 0.011(3) C3 0.067(3) 0.086(4) 0.039(2) 0.012(2) -0.008(2) -0.003(3) C4 0.065(3) 0.073(3) 0.051(2) -0.009(2) 0.002(2) -0.001(3) C5 0.043(2) 0.045(2) 0.054(2) -0.0017(18) 0.002(2) -0.002(2) C6 0.036(2) 0.040(2) 0.050(2) 0.0042(17) 0.0008(18) -0.0021(18) C7 0.044(3) 0.050(3) 0.075(3) -0.009(2) 0.005(2) 0.007(2) C1' 0.035(2) 0.0391(18) 0.048(2) -0.0007(16) -0.0021(16) 0.0029(16) C2' 0.031(2) 0.043(2) 0.060(3) -0.002(2) -0.002(2) -0.0049(19) C3' 0.048(3) 0.047(3) 0.058(3) -0.009(2) -0.008(2) 0.001(2) C4' 0.053(3) 0.045(2) 0.045(2) -0.002(2) -0.0007(18) 0.012(2) C5' 0.046(2) 0.042(2) 0.057(3) 0.0052(19) 0.007(2) -0.0030(19) C6' 0.041(2) 0.042(3) 0.061(3) 0.000(2) -0.004(2) -0.005(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 I C4' 2.102(4) . ? O C1 1.207(5) . ? C1 C2 1.460(6) . ? C1 C6 1.517(6) . ? C2 C3 1.317(7) . ? C3 C4 1.473(7) . ? C4 C5 1.529(6) . ? C5 C7 1.510(6) . ? C5 C6 1.542(5) . ? C6 C1' 1.513(6) . ? C1' C2' 1.375(6) . ? C1' C6' 1.397(6) . ? C2' C3' 1.383(6) . ? C3' C4' 1.376(6) . ? C4' C5' 1.373(6) . ? C5' C6' 1.377(6) . ? 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 O C1 C2 120.3(4) . . ? O C1 C6 123.6(4) . . ? C2 C1 C6 116.1(4) . . ? C3 C2 C1 122.8(5) . . ? C2 C3 C4 123.1(4) . . ? C3 C4 C5 113.8(4) . . ? C7 C5 C4 111.1(4) . . ? C7 C5 C6 112.7(4) . . ? C4 C5 C6 109.8(3) . . ? C1' C6 C1 111.9(3) . . ? C1' C6 C5 114.0(3) . . ? C1 C6 C5 111.0(3) . . ? C2' C1' C6' 117.9(4) . . ? C2' C1' C6 121.9(4) . . ? C6' C1' C6 120.2(4) . . ? C1' C2' C3' 121.7(4) . . ? C4' C3' C2' 119.0(4) . . ? C5' C4' C3' 121.0(4) . . ? C5' C4' I 119.7(3) . . ? C3' C4' I 119.3(3) . . ? C4' C5' C6' 119.3(4) . . ? C5' C6' C1' 121.2(4) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.597 _refine_diff_density_min -0.556 _refine_diff_density_rms 0.059