# 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 'Sun, Chung-Ming' _publ_contact_author_email cmsun@mail.nctu.edu.tw _publ_section_title ; Novel Cyclization of Bis-Boc-Guanidines: Expeditive Traceless Synthesis of 1,3,5-Oxadiazinones under Microwave Conditions ; _publ_author_name 'Chung-Ming Sun' data_cnbr16m _database_code_depnum_ccdc_archive 'CCDC 790233' #TrackingRef '2206_web_deposit_cif_file_0_GorakhS.Yellol_1282542582.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 N6 O2' _chemical_formula_sum 'C12 H16 N6 O2' _chemical_formula_weight 276.31 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3983(6) _cell_length_b 8.0111(6) _cell_length_c 11.8143(9) _cell_angle_alpha 82.0870(10) _cell_angle_beta 73.1960(10) _cell_angle_gamma 79.414(2) _cell_volume 656.24(9) _cell_formula_units_Z 2 _cell_measurement_temperature 297(2) _cell_measurement_reflns_used 2574 _cell_measurement_theta_min 2.596 _cell_measurement_theta_max 26.003 _exptl_crystal_description parallelepiped _exptl_crystal_colour colorless _exptl_crystal_size_max 0.63 _exptl_crystal_size_mid 0.61 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details empirical _exptl_special_details ; ? ; _diffrn_ambient_temperature 297(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_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 3742 _diffrn_reflns_av_R_equivalents 0.0140 _diffrn_reflns_av_sigmaI/netI 0.0156 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.01 _reflns_number_total 2530 _reflns_number_gt 2185 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1250P)^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 constro _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.067(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2530 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.2033 _refine_ls_wR_factor_gt 0.1925 _refine_ls_goodness_of_fit_ref 1.397 _refine_ls_restrained_S_all 1.397 _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 O1 O 0.21812(15) 0.92328(13) 0.61404(9) 0.0384(4) Uani 1 1 d . . . O2 O 0.17988(19) 0.72326(14) 0.51572(10) 0.0513(4) Uani 1 1 d . . . N1 N 0.27901(19) 1.11437(17) 0.71272(11) 0.0378(4) Uani 1 1 d . . . N2 N 0.23309(19) 0.97829(16) 0.40895(11) 0.0366(4) Uani 1 1 d . . . N3 N 0.30265(18) 1.18456(16) 0.51430(11) 0.0362(4) Uani 1 1 d . . . N4 N 0.2949(2) 1.24320(17) 0.32046(11) 0.0411(4) Uani 1 1 d . . . N5 N 0.1183(2) 1.51826(18) 0.19395(12) 0.0444(4) Uani 1 1 d . . . N6 N 0.2762(3) 1.6580(3) 0.00017(16) 0.0797(7) Uani 1 1 d . . . C1 C 0.3469(2) 1.2693(2) 0.72656(13) 0.0407(4) Uani 1 1 d . . . H1A H 0.2524 1.3695 0.7216 0.049 Uiso 1 1 calc R . . H1B H 0.4656 1.2851 0.6671 0.049 Uiso 1 1 calc R . . C2 C 0.3756(5) 1.2335(3) 0.84899(18) 0.0848(9) Uani 1 1 d . . . H2B H 0.5096 1.1947 0.8439 0.102 Uiso 1 1 calc R . . H2C H 0.3352 1.3364 0.8901 0.102 Uiso 1 1 calc R . . C3 C 0.2626(4) 1.1023(3) 0.91303(16) 0.0704(7) Uani 1 1 d . . . H3B H 0.1393 1.1541 0.9598 0.085 Uiso 1 1 calc R . . H3C H 0.3277 1.0290 0.9661 0.085 Uiso 1 1 calc R . . C4 C 0.2367(3) 1.0007(2) 0.82253(14) 0.0473(5) Uani 1 1 d . . . H4A H 0.3249 0.8945 0.8156 0.057 Uiso 1 1 calc R . . H4B H 0.1071 0.9760 0.8427 0.057 Uiso 1 1 calc R . . C5 C 0.2681(2) 1.07738(19) 0.60950(13) 0.0325(4) Uani 1 1 d . . . C6 C 0.2097(2) 0.86783(19) 0.50573(13) 0.0360(4) Uani 1 1 d . . . C7 C 0.2745(2) 1.13069(19) 0.41764(12) 0.0335(4) Uani 1 1 d . . . C8 C 0.2461(3) 1.2131(2) 0.21430(14) 0.0439(5) Uani 1 1 d . . . H8A H 0.2131 1.0994 0.2232 0.053 Uiso 1 1 calc R . . H8B H 0.3553 1.2211 0.1456 0.053 Uiso 1 1 calc R . . C9 C 0.0788(3) 1.3441(2) 0.19608(14) 0.0438(4) Uani 1 1 d . . . H9A H 0.0544 1.3305 0.1218 0.053 Uiso 1 1 calc R . . H9B H -0.0345 1.3258 0.2598 0.053 Uiso 1 1 calc R . . C10 C 0.1699(3) 1.5463(2) 0.30090(14) 0.0473(5) Uani 1 1 d . . . H10A H 0.0609 1.5386 0.3698 0.057 Uiso 1 1 calc R . . H10B H 0.2035 1.6597 0.2923 0.057 Uiso 1 1 calc R . . C11 C 0.3370(3) 1.4149(2) 0.31946(14) 0.0458(5) Uani 1 1 d . . . H11A H 0.4510 1.4328 0.2562 0.055 Uiso 1 1 calc R . . H11B H 0.3607 1.4274 0.3942 0.055 Uiso 1 1 calc R . . C12 C 0.2074(3) 1.5910(2) 0.09041(15) 0.0487(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 O1 0.0495(7) 0.0411(7) 0.0281(6) -0.0004(4) -0.0101(5) -0.0180(5) O2 0.0748(9) 0.0415(7) 0.0399(7) -0.0043(5) -0.0100(6) -0.0229(6) N1 0.0473(8) 0.0434(8) 0.0269(7) -0.0011(5) -0.0116(6) -0.0161(6) N2 0.0435(8) 0.0388(7) 0.0286(7) -0.0042(5) -0.0089(5) -0.0094(5) N3 0.0439(8) 0.0403(7) 0.0281(7) 0.0003(5) -0.0118(5) -0.0150(5) N4 0.0580(9) 0.0412(8) 0.0288(7) 0.0024(5) -0.0155(6) -0.0170(6) N5 0.0559(9) 0.0446(8) 0.0345(7) 0.0006(6) -0.0133(6) -0.0136(6) N6 0.1084(17) 0.0771(13) 0.0506(10) 0.0235(9) -0.0194(10) -0.0316(12) C1 0.0471(9) 0.0425(9) 0.0364(9) -0.0076(7) -0.0113(7) -0.0133(7) C2 0.145(2) 0.0917(17) 0.0459(12) 0.0027(11) -0.0430(13) -0.0687(17) C3 0.120(2) 0.0673(13) 0.0333(10) -0.0045(9) -0.0248(11) -0.0319(13) C4 0.0650(11) 0.0522(10) 0.0288(8) 0.0032(7) -0.0137(7) -0.0226(8) C5 0.0317(7) 0.0375(8) 0.0297(8) -0.0028(6) -0.0082(6) -0.0088(6) C6 0.0389(8) 0.0395(8) 0.0301(8) -0.0069(6) -0.0054(6) -0.0105(6) C7 0.0326(8) 0.0404(8) 0.0273(8) -0.0020(6) -0.0066(6) -0.0085(6) C8 0.0635(11) 0.0434(9) 0.0277(8) -0.0023(6) -0.0137(7) -0.0136(7) C9 0.0554(10) 0.0496(10) 0.0315(8) 0.0001(6) -0.0146(7) -0.0188(7) C10 0.0676(11) 0.0446(9) 0.0328(8) -0.0038(7) -0.0128(8) -0.0172(8) C11 0.0630(11) 0.0466(10) 0.0356(8) 0.0058(7) -0.0191(8) -0.0258(8) C12 0.0609(11) 0.0463(10) 0.0403(9) 0.0053(7) -0.0194(8) -0.0094(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 O1 C5 1.3422(18) . ? O1 C6 1.4324(17) . ? O2 C6 1.2020(18) . ? N1 C5 1.3216(19) . ? N1 C1 1.4668(19) . ? N1 C4 1.4678(19) . ? N2 C6 1.3355(19) . ? N2 C7 1.3361(19) . ? N3 C5 1.3101(18) . ? N3 C7 1.3563(18) . ? N4 C7 1.3484(19) . ? N4 C8 1.4623(19) . ? N4 C11 1.4631(19) . ? N5 C12 1.323(2) . ? N5 C9 1.473(2) . ? N5 C10 1.477(2) . ? N6 C12 1.146(2) . ? C1 C2 1.504(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.454(3) . ? C2 H2B 0.9700 . ? C2 H2C 0.9700 . ? C3 C4 1.502(2) . ? C3 H3B 0.9700 . ? C3 H3C 0.9700 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C8 C9 1.515(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.516(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? 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 O1 C6 117.82(11) . . ? C5 N1 C1 122.77(13) . . ? C5 N1 C4 123.71(14) . . ? C1 N1 C4 113.41(12) . . ? C6 N2 C7 117.69(13) . . ? C5 N3 C7 114.00(13) . . ? C7 N4 C8 122.16(13) . . ? C7 N4 C11 122.75(13) . . ? C8 N4 C11 114.38(12) . . ? C12 N5 C9 117.25(14) . . ? C12 N5 C10 118.30(14) . . ? C9 N5 C10 112.98(12) . . ? N1 C1 C2 102.30(13) . . ? N1 C1 H1A 111.3 . . ? C2 C1 H1A 111.3 . . ? N1 C1 H1B 111.3 . . ? C2 C1 H1B 111.3 . . ? H1A C1 H1B 109.2 . . ? C3 C2 C1 108.08(17) . . ? C3 C2 H2B 110.1 . . ? C1 C2 H2B 110.1 . . ? C3 C2 H2C 110.1 . . ? C1 C2 H2C 110.1 . . ? H2B C2 H2C 108.4 . . ? C2 C3 C4 107.44(16) . . ? C2 C3 H3B 110.2 . . ? C4 C3 H3B 110.2 . . ? C2 C3 H3C 110.2 . . ? C4 C3 H3C 110.2 . . ? H3B C3 H3C 108.5 . . ? N1 C4 C3 102.94(14) . . ? N1 C4 H4A 111.2 . . ? C3 C4 H4A 111.2 . . ? N1 C4 H4B 111.2 . . ? C3 C4 H4B 111.2 . . ? H4A C4 H4B 109.1 . . ? N3 C5 N1 121.62(14) . . ? N3 C5 O1 125.04(13) . . ? N1 C5 O1 113.34(13) . . ? O2 C6 N2 128.32(14) . . ? O2 C6 O1 113.44(13) . . ? N2 C6 O1 118.24(12) . . ? N2 C7 N4 117.64(13) . . ? N2 C7 N3 126.75(13) . . ? N4 C7 N3 115.60(13) . . ? N4 C8 C9 109.69(14) . . ? N4 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N4 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N5 C9 C8 110.80(13) . . ? N5 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? N5 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N5 C10 C11 110.63(14) . . ? N5 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? N5 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? N4 C11 C10 109.88(13) . . ? N4 C11 H11A 109.7 . . ? C10 C11 H11A 109.7 . . ? N4 C11 H11B 109.7 . . ? C10 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? N6 C12 N5 176.7(2) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.342 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.048