# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name _publ_author_address A.Martin ;Departamento Qu\'imica Inorg\'anica Edificio de Farmacia Campus Universitario E 28871 Alcal\'a de Henares (Madrid) SPAIN ; I.Castellote ;Departamento Qu\'imica Org\'anica Edificio de Farmacia Campus Universitario E 28871 Alcal\'a de Henares (Madrid) SPAIN ; "Mor\'on, M." ;Departamento Qu\'imica Org\'anica Edificio de Farmacia Campus Universitario E 28871 Alcal\'a de Henares (Madrid) SPAIN ; C.Burgos ;Departamento Qu\'imica Org\'anica Edificio de Farmacia Campus Universitario E 28871 Alcal\'a de Henares (Madrid) SPAIN ; J.Alvarez-Builla ;Departamento Qu\'imica Org\'anica Edificio de Farmacia Campus Universitario E 28871 Alcal\'a de Henares (Madrid) SPAIN ; ; P.Gomez-Sal ; ;Departamento Qu\'imica Inorg\'anica Edificio de Farmacia Campus Universitario E 28871 Alcal\'a de Henares (Madrid) SPAIN ; J.J.Vaquero ;Departamento Qu\'imica Org\'anica Edificio de Farmacia Campus Universitario E 28871 Alcal\'a de Henares (Madrid) SPAIN ; _publ_contact_author_address ;Departamento Qu\'imica Inorg\'anica Edificio de Farmacia Campus Universitario E 28871 Alcal\'a de Henares (Madrid) SPAIN ; _publ_contact_author_email JUANJOSE.VAQUERO@UAH.ES _publ_contact_author_fax 34918854683 _publ_contact_author_phone 34918854684 _publ_contact_author_name 'Prof. J.Vaquero' _publ_requested_category FO _publ_section_title ;Reaction of Imines with N-Iodosuccinimide (NIS): Unexpected Formation of Stable 1:1 Complexes ; data_import _database_code_depnum_ccdc_archive 'CCDC 207325' _audit_creation_date 2006-09-27T11:55:01-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H21 I1 N2 O4' _chemical_formula_sum 'C21 H21 I1 N2 O4' _chemical_formula_weight 492.3 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9590(2) _cell_length_b 12.0504(4) _cell_length_c 19.2674(11) _cell_angle_alpha 90 _cell_angle_beta 96.661(4) _cell_angle_gamma 90 _cell_volume 2066.06(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 17 0 0.18 -1 -17 0 0.14 -4 0 1 0.1 4 0 -1 0.11 0 0 -1 0.2 0 0 1 0.23 -1 11 9 0.134 1 2 5 0.165 -5 4 -7 0.168 3 -8 -1 0.136 6 7 -2 0.128 -9 3 2 0.086 -4 -12 3 0.126 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.579 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.7032 _exptl_absorpt_correction_T_max 0.8332 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type X=UH _diffrn_orient_matrix_ub_11 0.01 _diffrn_orient_matrix_ub_12 0 _diffrn_orient_matrix_ub_13 0 _diffrn_orient_matrix_ub_21 0 _diffrn_orient_matrix_ub_22 0.01 _diffrn_orient_matrix_ub_23 0 _diffrn_orient_matrix_ub_31 0 _diffrn_orient_matrix_ub_32 0 _diffrn_orient_matrix_ub_33 0.01 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0221 _diffrn_reflns_av_unetI/netI 0.0162 _diffrn_reflns_number 46207 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 5.02 _diffrn_reflns_theta_max 25.24 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.961 _diffrn_measured_fraction_theta_max 0.961 _reflns_number_total 3594 _reflns_number_gt 3260 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^+1.8370P] 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 none _refine_ls_number_reflns 3594 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0238 _refine_ls_R_factor_gt 0.0195 _refine_ls_wR_factor_ref 0.0623 _refine_ls_wR_factor_gt 0.0587 _refine_ls_goodness_of_fit_ref 0.843 _refine_ls_restrained_S_all 0.843 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.31 _refine_diff_density_min -0.465 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.7266(2) -0.0528(2) 1.17652(11) 0.0296(4) Uani 1 1 d . . . C3 C 0.5394(3) 0.0778(2) 1.19979(14) 0.0427(6) Uani 1 1 d . . . C4 C 0.5958(4) 0.1571(2) 1.14843(14) 0.0462(6) Uani 1 1 d . . . C4A C 0.6505(3) 0.0924(2) 1.08914(12) 0.0351(5) Uani 1 1 d . . . C5 C 0.6387(3) 0.1327(2) 1.02128(13) 0.0384(5) Uani 1 1 d . . . C6 C 0.6916(3) 0.0726(2) 0.96868(12) 0.0354(5) Uani 1 1 d . . . C7 C 0.7622(3) -0.03078(19) 0.98371(13) 0.0360(5) Uani 1 1 d . . . C8 C 0.7726(3) -0.0722(2) 1.05045(12) 0.0328(5) Uani 1 1 d . . . C8A C 0.7171(3) -0.01113(19) 1.10448(13) 0.0313(5) Uani 1 1 d . . . C9 C 0.8246(2) -0.1495(2) 1.19899(11) 0.0307(5) Uani 1 1 d . . . C10 C 0.9729(3) -0.1563(3) 1.18446(15) 0.0484(7) Uani 1 1 d . . . C11 C 1.0566(4) -0.2501(4) 1.20522(18) 0.0681(10) Uani 1 1 d . . . C12 C 0.9967(4) -0.3357(3) 1.23959(17) 0.0627(9) Uani 1 1 d . . . C13 C 0.8509(3) -0.3295(2) 1.25428(14) 0.0470(6) Uani 1 1 d . . . C14 C 0.7657(3) -0.2371(2) 1.23406(12) 0.0354(5) Uani 1 1 d . . . C16 C 0.6015(4) 0.2066(3) 0.88346(16) 0.0492(7) Uani 1 1 d . . . C18 C 0.9039(5) -0.1797(3) 0.94311(17) 0.0590(8) Uani 1 1 d . . . C21 C 0.8364(3) 0.0654(3) 1.49675(14) 0.0462(6) Uani 1 1 d . . . C23 C 0.8261(4) 0.0536(4) 1.57426(16) 0.0643(9) Uani 1 1 d . . . C24 C 0.7247(5) -0.0439(4) 1.58060(17) 0.0680(10) Uani 1 1 d . . . C25 C 0.6632(3) -0.0736(3) 1.50639(14) 0.0491(6) Uani 1 1 d . . . I19 I 0.697777(15) -0.022050(13) 1.351691(7) 0.03333(8) Uani 1 1 d . . . N2 N 0.6486(2) -0.01059(17) 1.22225(11) 0.0346(4) Uani 1 1 d . . . N20 N 0.7377(3) -0.01037(18) 1.46209(11) 0.0383(5) Uani 1 1 d . . . O15 O 0.6808(2) 0.10530(16) 0.90047(9) 0.0457(4) Uani 1 1 d . . . O17 O 0.8138(2) -0.08301(17) 0.92778(9) 0.0519(5) Uani 1 1 d . . . O22 O 0.9140(3) 0.1281(2) 1.46809(13) 0.0693(6) Uani 1 1 d . . . O26 O 0.5676(3) -0.1405(2) 1.48832(13) 0.0782(7) Uani 1 1 d . . . H5 H 0.601(3) 0.197(3) 1.0109(15) 0.048(8) Uiso 1 1 d . . . H8 H 0.818(3) -0.143(2) 1.0595(14) 0.039(7) Uiso 1 1 d . . . H10 H 1.017(3) -0.097(3) 1.1614(15) 0.045(8) Uiso 1 1 d . . . H11 H 1.147(4) -0.260(3) 1.191(2) 0.082(12) Uiso 1 1 d . . . H12 H 1.055(4) -0.401(3) 1.2521(18) 0.067(10) Uiso 1 1 d . . . H13 H 0.811(3) -0.388(3) 1.2758(16) 0.049(8) Uiso 1 1 d . . . H14 H 0.667(3) -0.233(2) 1.2438(15) 0.044(7) Uiso 1 1 d . . . H31 H 0.455(3) 0.044(2) 1.1769(15) 0.038(7) Uiso 1 1 d . . . H32 H 0.511(3) 0.116(3) 1.2400(16) 0.043(7) Uiso 1 1 d . . . H41 H 0.670(3) 0.202(3) 1.1695(16) 0.050(8) Uiso 1 1 d . . . H42 H 0.512(3) 0.210(3) 1.1302(16) 0.052(8) Uiso 1 1 d . . . H161 H 0.497(4) 0.205(3) 0.8960(17) 0.062(9) Uiso 1 1 d . . . H162 H 0.665(4) 0.270(3) 0.9051(18) 0.065(9) Uiso 1 1 d . . . H163 H 0.603(3) 0.207(2) 0.8328(17) 0.046(7) Uiso 1 1 d . . . H181 H 0.940(4) -0.204(3) 0.902(2) 0.080(11) Uiso 1 1 d . . . H182 H 0.989(4) -0.163(3) 0.983(2) 0.071(10) Uiso 1 1 d . . . H183 H 0.839(5) -0.231(4) 0.960(2) 0.086(13) Uiso 1 1 d . . . H231 H 0.794(6) 0.115(5) 1.591(3) 0.13(2) Uiso 1 1 d . . . H232 H 0.920(6) 0.041(4) 1.597(3) 0.098(15) Uiso 1 1 d . . . H241 H 0.649(6) -0.027(4) 1.607(3) 0.101(16) Uiso 1 1 d . . . H242 H 0.783(5) -0.102(4) 1.599(2) 0.084(13) Uiso 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 0.0298(10) 0.0324(12) 0.0261(11) -0.0016(9) 0.0007(8) 0.0004(9) C3 0.0479(15) 0.0456(16) 0.0347(13) -0.0058(11) 0.0049(11) 0.0173(12) C4 0.0611(17) 0.0368(15) 0.0390(14) -0.0049(11) -0.0013(12) 0.0178(13) C4A 0.0392(12) 0.0321(13) 0.0331(12) 0.0001(10) -0.0004(9) 0.0046(9) C5 0.0441(13) 0.0303(13) 0.0391(13) 0.0056(11) -0.0026(10) 0.0058(10) C6 0.0369(12) 0.0387(13) 0.0294(11) 0.0070(10) -0.0009(9) -0.0018(10) C7 0.0422(13) 0.0366(14) 0.0291(12) 0.0006(9) 0.0041(10) 0.0042(10) C8 0.0398(12) 0.0299(12) 0.0287(11) 0.0020(9) 0.0035(9) 0.0073(10) C8A 0.0337(12) 0.0306(12) 0.0288(12) 0.0014(9) 0.0005(9) 0.0034(9) C9 0.0324(11) 0.0377(13) 0.0219(10) -0.0026(9) 0.0019(8) 0.0069(9) C10 0.0398(13) 0.0624(18) 0.0445(15) 0.0158(13) 0.0109(11) 0.0101(13) C11 0.0425(16) 0.100(3) 0.065(2) 0.0238(19) 0.0193(14) 0.0336(17) C12 0.0664(19) 0.066(2) 0.0564(19) 0.0192(16) 0.0087(15) 0.0366(17) C13 0.0603(16) 0.0425(16) 0.0379(14) 0.0067(12) 0.0048(12) 0.0099(13) C14 0.0374(13) 0.0389(14) 0.0293(12) 0.0009(10) 0.0022(9) 0.0038(10) C16 0.0540(17) 0.0467(17) 0.0450(16) 0.0193(13) -0.0024(12) 0.0006(13) C18 0.081(2) 0.057(2) 0.0410(16) -0.0023(14) 0.0158(16) 0.0279(18) C21 0.0474(14) 0.0500(16) 0.0393(14) -0.0071(12) -0.0025(11) -0.0009(13) C23 0.065(2) 0.090(3) 0.0361(15) -0.0149(16) -0.0022(14) 0.0059(19) C24 0.071(2) 0.101(3) 0.0328(16) 0.0105(16) 0.0099(15) 0.005(2) C25 0.0540(16) 0.0546(18) 0.0402(14) 0.0066(13) 0.0120(12) -0.0022(14) I19 0.03628(11) 0.03342(12) 0.03092(11) -0.00335(5) 0.00657(7) -0.00138(5) N2 0.0368(11) 0.0379(11) 0.0287(10) -0.0032(8) 0.0016(8) 0.0076(8) N20 0.0433(12) 0.0419(12) 0.0296(11) -0.0034(9) 0.0042(9) -0.0043(9) O15 0.0591(11) 0.0447(10) 0.0327(9) 0.0132(8) 0.0023(8) 0.0058(8) O17 0.0726(13) 0.0574(13) 0.0270(9) 0.0046(8) 0.0104(8) 0.0271(10) O22 0.0736(14) 0.0680(15) 0.0649(14) -0.0055(12) 0.0014(11) -0.0324(12) O26 0.0921(17) 0.0792(17) 0.0656(15) 0.0052(13) 0.0187(13) -0.0415(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 N2 1.291(3) . ? C1 C8A 1.469(3) . ? C1 C9 1.493(3) . ? C3 N2 1.477(3) . ? C3 C4 1.505(4) . ? C4 C4A 1.511(3) . ? C4A C5 1.387(3) . ? C4A C8A 1.400(3) . ? C5 C6 1.374(4) . ? C6 O15 1.365(3) . ? C6 C7 1.412(4) . ? C7 O17 1.374(3) . ? C7 C8 1.373(3) . ? C8 C8A 1.412(3) . ? C9 C14 1.390(4) . ? C9 C10 1.392(3) . ? C10 C11 1.390(4) . ? C11 C12 1.369(5) . ? C12 C13 1.370(4) . ? C13 C14 1.381(4) . ? C16 O15 1.431(3) . ? C18 O17 1.429(4) . ? C21 O22 1.204(4) . ? C21 N20 1.387(4) . ? C21 C23 1.514(4) . ? C23 C24 1.499(6) . ? C24 C25 1.514(4) . ? C25 O26 1.198(4) . ? C25 N20 1.374(3) . ? I19 N20 2.120(2) . ? I19 N2 2.486(2) . ? 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 N2 C1 C8A 122.3(2) . . ? N2 C1 C9 117.2(2) . . ? C8A C1 C9 120.53(19) . . ? N2 C3 C4 112.9(2) . . ? C4A C4 C3 109.4(2) . . ? C5 C4A C8A 119.7(2) . . ? C5 C4A C4 122.4(2) . . ? C8A C4A C4 117.9(2) . . ? C6 C5 C4A 121.1(2) . . ? O15 C6 C5 124.5(2) . . ? O15 C6 C7 115.6(2) . . ? C5 C6 C7 119.9(2) . . ? O17 C7 C8 125.1(2) . . ? O17 C7 C6 115.3(2) . . ? C8 C7 C6 119.6(2) . . ? C7 C8 C8A 120.6(2) . . ? C4A C8A C8 119.2(2) . . ? C4A C8A C1 118.7(2) . . ? C8 C8A C1 122.1(2) . . ? C14 C9 C10 118.6(2) . . ? C14 C9 C1 119.34(19) . . ? C10 C9 C1 122.1(2) . . ? C11 C10 C9 119.1(3) . . ? C12 C11 C10 121.6(3) . . ? C11 C12 C13 119.7(3) . . ? C12 C13 C14 119.7(3) . . ? C13 C14 C9 121.4(2) . . ? O22 C21 N20 124.2(3) . . ? O22 C21 C23 128.0(3) . . ? N20 C21 C23 107.7(3) . . ? C21 C23 C24 105.1(3) . . ? C23 C24 C25 105.4(3) . . ? O26 C25 N20 125.1(3) . . ? O26 C25 C24 127.1(3) . . ? N20 C25 C24 107.8(3) . . ? N20 I19 N2 172.99(8) . . ? C1 N2 C3 118.5(2) . . ? C1 N2 I19 128.03(16) . . ? C3 N2 I19 111.61(15) . . ? C25 N20 C21 113.2(2) . . ? C25 N20 I19 123.28(18) . . ? C21 N20 I19 123.41(18) . . ? C6 O15 C16 116.4(2) . . ? C7 O17 C18 116.4(2) . . ?