# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jing-Mei Huang' _publ_contact_author_email chehjm@scut.edu.cn loop_ _publ_author_name 'Jing-Mei Huang' 'Zhi-Jun Ye' 'Dong-song Chen' 'Hong Zhu' data_ltp64 _database_code_depnum_ccdc_archive 'CCDC 838337' #TrackingRef 'web_deposit_cif_file_0_Jing-MeiHuang_1312766132.ltp64.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_absolute_configuration ad _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 I N O' _chemical_formula_sum 'C18 H20 I N O' _chemical_formula_weight 393.25 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 Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 10.3319(4) _cell_length_b 21.2699(8) _cell_length_c 9.3647(4) _cell_angle_alpha 90.00 _cell_angle_beta 120.648(2) _cell_angle_gamma 90.00 _cell_volume 1770.50(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 8170 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 30.47 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 1.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6131 _exptl_absorpt_correction_T_max 0.7138 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12308 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0331 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 30.52 _reflns_number_total 4293 _reflns_number_gt 4053 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0501P)^2^+2.6421P] 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 -0.02(3) _refine_ls_number_reflns 4293 _refine_ls_number_parameters 191 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.1084 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.002 _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 C1 C 0.6085(5) 0.78335(19) 0.2899(6) 0.0400(8) Uani 1 1 d . . . H1A H 0.5315 0.7897 0.1716 0.048 Uiso 1 1 calc R . . H1B H 0.5732 0.7491 0.3332 0.048 Uiso 1 1 calc R . . C2 C 0.6226(4) 0.84380(16) 0.3855(5) 0.0325(7) Uani 1 1 d . . . H2 H 0.6665 0.8772 0.3476 0.039 Uiso 1 1 calc R . . C3 C 0.7222(4) 0.83693(17) 0.5725(5) 0.0334(7) Uani 1 1 d . . . C4 C 0.6881(5) 0.7946(2) 0.6605(6) 0.0426(9) Uani 1 1 d . . . H4 H 0.6057 0.7665 0.6030 0.051 Uiso 1 1 calc R . . C5 C 0.7746(6) 0.7929(2) 0.8345(7) 0.0525(12) Uani 1 1 d . . . H5 H 0.7507 0.7635 0.8939 0.063 Uiso 1 1 calc R . . C6 C 0.8946(6) 0.8338(3) 0.9207(6) 0.0534(13) Uani 1 1 d . . . H6 H 0.9512 0.8335 1.0385 0.064 Uiso 1 1 calc R . . C7 C 0.9298(6) 0.8747(3) 0.8321(6) 0.0514(12) Uani 1 1 d . . . H7 H 1.0136 0.9021 0.8891 0.062 Uiso 1 1 calc R . . C8 C 0.8440(5) 0.8765(2) 0.6600(6) 0.0409(9) Uani 1 1 d . . . H8 H 0.8696 0.9055 0.6011 0.049 Uiso 1 1 calc R . . C9 C 0.4617(4) 0.86352(17) 0.3355(5) 0.0326(7) Uani 1 1 d . . . H9A H 0.4053 0.8729 0.2152 0.039 Uiso 1 1 calc R . . H9B H 0.4114 0.8276 0.3544 0.039 Uiso 1 1 calc R . . C10 C 0.4522(4) 0.92082(16) 0.4292(4) 0.0289(6) Uani 1 1 d . . . H10 H 0.5175 0.9124 0.5508 0.035 Uiso 1 1 calc R . . C11 C 0.2918(4) 0.92876(16) 0.3919(5) 0.0323(7) Uani 1 1 d . . . C12 C 0.1860(5) 0.9644(2) 0.2582(6) 0.0449(10) Uani 1 1 d . . . H12 H 0.2138 0.9863 0.1893 0.054 Uiso 1 1 calc R . . C13 C 0.0382(6) 0.9676(2) 0.2265(8) 0.0563(13) Uani 1 1 d . . . H13 H -0.0343 0.9916 0.1348 0.068 Uiso 1 1 calc R . . C14 C -0.0044(5) 0.9366(3) 0.3258(7) 0.0538(12) Uani 1 1 d . . . H14 H -0.1046 0.9398 0.3040 0.065 Uiso 1 1 calc R . . C15 C 0.1000(6) 0.9014(3) 0.4559(7) 0.0516(11) Uani 1 1 d . . . H15 H 0.0716 0.8800 0.5246 0.062 Uiso 1 1 calc R . . C16 C 0.2471(5) 0.8964(2) 0.4893(5) 0.0418(9) Uani 1 1 d . . . H16 H 0.3175 0.8710 0.5787 0.050 Uiso 1 1 calc R . . C17 C 0.5572(5) 1.02681(18) 0.4878(5) 0.0317(7) Uani 1 1 d . . . C18 C 0.6095(5) 1.0823(2) 0.4335(5) 0.0403(9) Uani 1 1 d . . . H18A H 0.5268 1.1125 0.3771 0.061 Uiso 1 1 calc R . . H18B H 0.6423 1.0686 0.3570 0.061 Uiso 1 1 calc R . . H18C H 0.6938 1.1024 0.5306 0.061 Uiso 1 1 calc R . . I1 I 0.81579(7) 0.754913(14) 0.30699(8) 0.05164(11) Uani 1 1 d . . . N1 N 0.5104(4) 0.97683(16) 0.3901(4) 0.0300(6) Uani 1 1 d . . . H1 H 0.5145 0.9773 0.2984 0.036 Uiso 1 1 calc R . . O1 O 0.5588(5) 1.02866(16) 0.6212(4) 0.0516(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 0.052(2) 0.0350(18) 0.038(2) -0.0105(16) 0.0259(19) -0.0027(16) C2 0.0434(19) 0.0262(14) 0.0310(18) -0.0026(13) 0.0213(16) -0.0036(13) C3 0.0365(17) 0.0292(15) 0.0345(19) -0.0048(14) 0.0182(15) 0.0028(13) C4 0.053(2) 0.0325(18) 0.045(2) 0.0031(17) 0.027(2) 0.0063(16) C5 0.075(3) 0.043(2) 0.052(3) 0.014(2) 0.041(3) 0.026(2) C6 0.066(3) 0.057(3) 0.030(2) -0.002(2) 0.019(2) 0.033(2) C7 0.048(2) 0.059(3) 0.036(2) -0.022(2) 0.0130(19) 0.004(2) C8 0.0379(19) 0.042(2) 0.040(2) -0.0080(17) 0.0185(17) -0.0044(15) C9 0.0397(18) 0.0287(15) 0.0261(17) -0.0015(13) 0.0144(15) -0.0024(13) C10 0.0379(17) 0.0263(14) 0.0253(16) -0.0007(12) 0.0180(14) -0.0025(12) C11 0.0405(18) 0.0260(14) 0.0317(18) -0.0053(13) 0.0193(15) -0.0054(13) C12 0.051(2) 0.039(2) 0.045(3) 0.0046(19) 0.025(2) -0.0032(18) C13 0.045(2) 0.044(2) 0.066(4) 0.002(2) 0.018(2) 0.0071(19) C14 0.040(2) 0.062(3) 0.061(3) -0.023(3) 0.027(2) -0.007(2) C15 0.048(2) 0.065(3) 0.050(3) -0.010(2) 0.031(2) -0.016(2) C16 0.043(2) 0.047(2) 0.034(2) 0.0052(17) 0.0187(17) -0.0076(17) C17 0.0427(19) 0.0326(16) 0.0249(18) -0.0029(14) 0.0210(15) -0.0062(14) C18 0.053(2) 0.0373(18) 0.0311(19) -0.0018(15) 0.0220(18) -0.0178(17) I1 0.05660(16) 0.05708(17) 0.04384(16) -0.00883(18) 0.02748(12) 0.00951(19) N1 0.0442(17) 0.0316(15) 0.0223(13) -0.0006(12) 0.0229(13) -0.0014(13) O1 0.093(3) 0.0421(15) 0.0384(17) -0.0131(14) 0.0475(18) -0.0239(16) _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 1.531(5) . ? C1 I1 2.151(4) . ? C2 C3 1.519(5) . ? C2 C9 1.538(5) . ? C3 C8 1.383(6) . ? C3 C4 1.383(6) . ? C4 C5 1.404(7) . ? C5 C6 1.387(8) . ? C6 C7 1.374(8) . ? C7 C8 1.389(7) . ? C9 C10 1.534(5) . ? C10 N1 1.463(5) . ? C10 C11 1.519(5) . ? C11 C12 1.393(6) . ? C11 C16 1.395(6) . ? C12 C13 1.401(7) . ? C13 C14 1.382(9) . ? C14 C15 1.367(8) . ? C15 C16 1.391(7) . ? C17 O1 1.241(4) . ? C17 N1 1.323(5) . ? C17 C18 1.492(5) . ? 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 I1 113.5(3) . . ? C3 C2 C1 113.6(3) . . ? C3 C2 C9 111.7(3) . . ? C1 C2 C9 106.6(3) . . ? C8 C3 C4 118.4(4) . . ? C8 C3 C2 120.1(4) . . ? C4 C3 C2 121.4(4) . . ? C3 C4 C5 120.2(4) . . ? C6 C5 C4 120.7(5) . . ? C7 C6 C5 118.7(4) . . ? C6 C7 C8 120.6(5) . . ? C3 C8 C7 121.4(5) . . ? C10 C9 C2 114.6(3) . . ? N1 C10 C11 113.0(3) . . ? N1 C10 C9 110.4(3) . . ? C11 C10 C9 109.7(3) . . ? C12 C11 C16 119.1(4) . . ? C12 C11 C10 122.1(4) . . ? C16 C11 C10 118.7(4) . . ? C11 C12 C13 119.2(5) . . ? C14 C13 C12 121.4(5) . . ? C15 C14 C13 118.9(5) . . ? C14 C15 C16 121.2(5) . . ? C15 C16 C11 120.2(4) . . ? O1 C17 N1 122.3(4) . . ? O1 C17 C18 119.8(4) . . ? N1 C17 C18 117.9(3) . . ? C17 N1 C10 122.2(3) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.194 _refine_diff_density_min -1.047 _refine_diff_density_rms 0.194