Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dilip Maiti' _publ_contact_author_email MAITIDK@YAHOO.COM _publ_section_title ; Generation of Azomethine Imine and Metal Free Formal 1,3-Dipolar Cycloaddition of Imine with PhIO: Reaction, Scope, and Synthesis ; loop_ _publ_author_name 'Dilip Maiti' 'Nirbhik Chatterjee' 'Sandip K. Hota' 'Palash Pandit' # Attachment 'CrystallographicInformationFile.cif' data_5nir272_0m _database_code_depnum_ccdc_archive 'CCDC 741300' #TrackingRef 'CrystallographicInformationFile.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H15 Cl2 N3' _chemical_formula_weight 380.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 11.1316(8) _cell_length_b 14.5857(11) _cell_length_c 21.9255(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3559.9(4) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2326 _cell_measurement_theta_min 2.476 _cell_measurement_theta_max 25.330 _exptl_crystal_description rectangular _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1568 _exptl_absorpt_coefficient_mu 0.374 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.994 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 Kappa Apex 2' _diffrn_measurement_method 'Difference vectors' _diffrn_detector_area_resol_mean 512X512 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16801 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.33 _reflns_number_total 3216 _reflns_number_gt 2326 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex 2, Bruker Kappa' _computing_cell_refinement 'Apex 2, Bruker Kappa' _computing_data_reduction 'Apex 2, Bruker Kappa' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON(Spek,2004) _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^)+(0.1000P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.0086(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3216 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0597 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.962 _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 Cl1 Cl 1.09181(6) 0.19986(6) 0.24051(3) 0.0870(3) Uani 1 1 d . . . Cl2 Cl 0.26709(7) 0.07420(6) -0.22260(4) 0.0956(3) Uani 1 1 d . . . C6 C 0.55628(16) 0.23715(13) 0.05793(9) 0.0400(5) Uani 1 1 d . . . C9 C 0.66240(16) 0.06872(14) -0.04212(9) 0.0424(5) Uani 1 1 d . . . C8 C 0.78793(17) 0.08306(13) 0.03233(9) 0.0420(5) Uani 1 1 d . . . C7 C 0.65544(18) 0.22104(13) 0.01232(10) 0.0451(5) Uani 1 1 d . . . H7A H 0.6291 0.2442 -0.0269 0.054 Uiso 1 1 calc R . . H7B H 0.7247 0.2569 0.0246 0.054 Uiso 1 1 calc R . . C21 C 0.98040(18) 0.09821(16) 0.08356(10) 0.0521(6) Uani 1 1 d . . . H21 H 1.0145 0.0690 0.0500 0.063 Uiso 1 1 calc R . . C10 C 0.56538(18) 0.08062(13) -0.08639(9) 0.0432(5) Uani 1 1 d . . . C18 C 0.8812(2) 0.18387(17) 0.18254(11) 0.0598(6) Uani 1 1 d . . . H18 H 0.8478 0.2125 0.2164 0.072 Uiso 1 1 calc R . . C12 C 0.3579(2) 0.09958(17) -0.11157(11) 0.0594(6) Uani 1 1 d . . . H12 H 0.2796 0.1132 -0.0999 0.071 Uiso 1 1 calc R . . C16 C 0.85861(17) 0.11577(14) 0.08403(9) 0.0443(5) Uani 1 1 d . . . C5 C 0.5252(2) 0.32633(14) 0.07090(10) 0.0511(5) Uani 1 1 d . . . H5 H 0.5672 0.3743 0.0528 0.061 Uiso 1 1 calc R . . C19 C 1.00167(19) 0.16659(17) 0.18030(10) 0.0539(6) Uani 1 1 d . . . C20 C 1.0517(2) 0.12294(17) 0.13140(11) 0.0579(6) Uani 1 1 d . . . H20 H 1.1335 0.1102 0.1307 0.069 Uiso 1 1 calc R . . C15 C 0.58822(19) 0.05927(16) -0.14647(10) 0.0540(6) Uani 1 1 d . . . H15 H 0.6665 0.0464 -0.1585 0.065 Uiso 1 1 calc R . . C1 C 0.49360(18) 0.16681(14) 0.08564(10) 0.0479(5) Uani 1 1 d . . . H1 H 0.5143 0.1062 0.0778 0.058 Uiso 1 1 calc R . . C11 C 0.44927(19) 0.10185(16) -0.06938(10) 0.0529(6) Uani 1 1 d . . . H11 H 0.4327 0.1178 -0.0292 0.063 Uiso 1 1 calc R . . C17 C 0.80996(19) 0.15877(16) 0.13447(10) 0.0540(6) Uani 1 1 d . . . H17 H 0.7279 0.1708 0.1358 0.065 Uiso 1 1 calc R . . C2 C 0.4004(2) 0.18652(16) 0.12492(11) 0.0559(6) Uani 1 1 d . . . H2 H 0.3583 0.1389 0.1434 0.067 Uiso 1 1 calc R . . C14 C 0.4978(2) 0.05667(18) -0.18881(11) 0.0641(7) Uani 1 1 d . . . H14 H 0.5137 0.0413 -0.2292 0.077 Uiso 1 1 calc R . . C4 C 0.4325(2) 0.34517(16) 0.11050(11) 0.0597(6) Uani 1 1 d . . . H4 H 0.4126 0.4057 0.1193 0.072 Uiso 1 1 calc R . . C13 C 0.3828(2) 0.07731(17) -0.17026(11) 0.0578(6) Uani 1 1 d . . . C3 C 0.3694(2) 0.27505(17) 0.13700(11) 0.0595(6) Uani 1 1 d . . . H3 H 0.3057 0.2878 0.1631 0.071 Uiso 1 1 calc R . . N1 N 0.69354(13) 0.12612(11) 0.00450(7) 0.0396(4) Uani 1 1 d . . . N3 N 0.73144(15) -0.00357(12) -0.04259(8) 0.0489(5) Uani 1 1 d . . . N2 N 0.81129(16) 0.00592(12) 0.00488(8) 0.0498(5) 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 Cl1 0.0629(4) 0.1386(7) 0.0597(5) -0.0120(4) -0.0161(3) -0.0117(4) Cl2 0.0773(5) 0.1333(7) 0.0762(6) 0.0116(4) -0.0352(4) -0.0104(5) C6 0.0340(10) 0.0430(11) 0.0429(12) -0.0019(9) -0.0039(8) 0.0009(8) C9 0.0349(10) 0.0498(12) 0.0424(12) -0.0013(9) 0.0033(8) -0.0028(9) C8 0.0354(10) 0.0477(12) 0.0430(12) -0.0014(9) 0.0043(8) 0.0029(8) C7 0.0423(11) 0.0444(11) 0.0487(13) -0.0012(9) 0.0019(9) -0.0003(9) C21 0.0405(11) 0.0628(13) 0.0531(14) -0.0073(11) 0.0049(10) 0.0051(10) C10 0.0425(11) 0.0446(11) 0.0424(13) 0.0026(9) 0.0019(8) -0.0028(9) C18 0.0497(13) 0.0822(16) 0.0474(15) -0.0130(12) 0.0006(10) 0.0056(12) C12 0.0419(12) 0.0749(15) 0.0613(16) 0.0044(12) -0.0036(11) 0.0042(11) C16 0.0379(10) 0.0518(11) 0.0433(12) -0.0007(9) 0.0012(8) 0.0026(9) C5 0.0480(12) 0.0449(12) 0.0604(14) 0.0018(10) -0.0015(10) 0.0025(10) C19 0.0481(13) 0.0704(15) 0.0431(13) 0.0016(11) -0.0054(10) -0.0025(11) C20 0.0368(11) 0.0762(16) 0.0606(16) -0.0020(12) -0.0037(10) 0.0017(11) C15 0.0449(12) 0.0739(15) 0.0431(14) -0.0005(11) 0.0046(9) -0.0051(11) C1 0.0478(12) 0.0416(11) 0.0544(14) -0.0045(9) 0.0040(9) 0.0011(9) C11 0.0454(12) 0.0668(14) 0.0464(13) 0.0004(11) 0.0002(10) 0.0064(11) C17 0.0401(11) 0.0752(15) 0.0467(14) -0.0065(12) 0.0018(9) 0.0093(11) C2 0.0484(13) 0.0586(14) 0.0606(16) 0.0013(11) 0.0097(11) -0.0040(11) C14 0.0661(15) 0.0827(17) 0.0436(14) 0.0019(12) 0.0000(11) -0.0100(13) C4 0.0623(15) 0.0493(13) 0.0676(16) -0.0070(12) 0.0044(12) 0.0161(12) C13 0.0539(13) 0.0678(15) 0.0516(16) 0.0102(11) -0.0139(11) -0.0084(11) C3 0.0517(13) 0.0690(16) 0.0579(16) -0.0060(12) 0.0104(11) 0.0129(12) N1 0.0349(8) 0.0425(9) 0.0415(10) -0.0018(7) 0.0026(7) 0.0031(7) N3 0.0434(9) 0.0522(11) 0.0511(11) -0.0076(8) -0.0012(8) 0.0046(8) N2 0.0431(10) 0.0543(11) 0.0519(12) -0.0075(9) -0.0014(8) 0.0065(8) _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 Cl1 C19 1.728(2) . ? Cl2 C13 1.726(2) . ? C6 C5 1.376(3) . ? C6 C1 1.381(3) . ? C6 C7 1.508(3) . ? C9 N3 1.305(3) . ? C9 N1 1.366(2) . ? C9 C10 1.463(3) . ? C8 N2 1.302(3) . ? C8 N1 1.368(2) . ? C8 C16 1.460(3) . ? C7 N1 1.458(2) . ? C21 C20 1.364(3) . ? C21 C16 1.380(3) . ? C10 C15 1.377(3) . ? C10 C11 1.380(3) . ? C18 C19 1.366(3) . ? C18 C17 1.369(3) . ? C12 C13 1.356(3) . ? C12 C11 1.375(3) . ? C16 C17 1.382(3) . ? C5 C4 1.377(3) . ? C19 C20 1.366(3) . ? C15 C14 1.370(3) . ? C1 C2 1.379(3) . ? C2 C3 1.363(3) . ? C14 C13 1.376(3) . ? C4 C3 1.370(3) . ? N3 N2 1.376(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 C5 C6 C1 118.97(19) . . ? C5 C6 C7 117.93(18) . . ? C1 C6 C7 123.07(17) . . ? N3 C9 N1 110.60(17) . . ? N3 C9 C10 121.71(18) . . ? N1 C9 C10 127.68(18) . . ? N2 C8 N1 110.12(18) . . ? N2 C8 C16 122.25(18) . . ? N1 C8 C16 127.61(17) . . ? N1 C7 C6 116.03(16) . . ? C20 C21 C16 121.1(2) . . ? C15 C10 C11 118.8(2) . . ? C15 C10 C9 118.14(18) . . ? C11 C10 C9 122.60(19) . . ? C19 C18 C17 119.5(2) . . ? C13 C12 C11 119.5(2) . . ? C21 C16 C17 118.38(19) . . ? C21 C16 C8 117.58(18) . . ? C17 C16 C8 123.95(18) . . ? C6 C5 C4 120.5(2) . . ? C18 C19 C20 121.0(2) . . ? C18 C19 Cl1 119.42(19) . . ? C20 C19 Cl1 119.62(17) . . ? C21 C20 C19 119.3(2) . . ? C14 C15 C10 121.2(2) . . ? C2 C1 C6 119.99(19) . . ? C12 C11 C10 120.3(2) . . ? C18 C17 C16 120.7(2) . . ? C3 C2 C1 120.6(2) . . ? C15 C14 C13 118.5(2) . . ? C3 C4 C5 120.2(2) . . ? C12 C13 C14 121.5(2) . . ? C12 C13 Cl2 118.99(19) . . ? C14 C13 Cl2 119.5(2) . . ? C2 C3 C4 119.7(2) . . ? C9 N1 C8 104.31(16) . . ? C9 N1 C7 126.60(17) . . ? C8 N1 C7 127.37(17) . . ? C9 N3 N2 107.05(16) . . ? C8 N2 N3 107.92(16) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.33 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.168 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.036