# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Jiang, Bo' 'Wang, Xiang' 'Shi, Feng' "Tu, Shujiang''Li, Guigen" _publ_contact_author_name 'Dr Guigen Li' _publ_contact_author_email guigen.li@ttu.edu _publ_section_title ; New multicomponent cyclization: domino synthesis of pentasubstituted pyridines under solvent-free condition ; # Attachment '- 3a.cif' data_090220a _database_code_depnum_ccdc_archive 'CCDC 806791' #TrackingRef '- 3a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H19 N5' _chemical_formula_weight 281.36 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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' '-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 9.0838(14) _cell_length_b 24.279(2) _cell_length_c 14.5751(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.451(2) _cell_angle_gamma 90.00 _cell_volume 3138.9(7) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1359 _cell_measurement_theta_min 2.205 _cell_measurement_theta_max 28.236 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9815 _exptl_absorpt_correction_T_max 0.9933 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 8272 _diffrn_reflns_av_R_equivalents 0.0962 _diffrn_reflns_av_sigmaI/netI 0.0896 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2770 _reflns_number_gt 1373 _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^)+(0.0828P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2770 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1430 _refine_ls_R_factor_gt 0.0721 _refine_ls_wR_factor_ref 0.1987 _refine_ls_wR_factor_gt 0.1719 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 N1 N 0.4896(3) 0.07355(11) 1.12388(17) 0.0436(7) Uani 1 1 d . . . N2 N 0.6988(3) 0.05700(12) 1.23599(18) 0.0548(8) Uani 1 1 d . . . H2A H 0.6444 0.0624 1.2767 0.066 Uiso 1 1 calc R . . H2B H 0.7928 0.0491 1.2543 0.066 Uiso 1 1 calc R . . N3 N 0.9971(3) 0.02303(14) 1.1251(2) 0.0703(10) Uani 1 1 d . . . N4 N 0.7289(3) 0.05221(12) 0.91381(17) 0.0522(8) Uani 1 1 d . . . H4A H 0.8226 0.0431 0.9278 0.063 Uiso 1 1 calc R . . H4B H 0.6840 0.0566 0.8560 0.063 Uiso 1 1 calc R . . N5 N 0.3551(4) 0.08063(15) 0.7912(2) 0.0744(10) Uani 1 1 d . . . C1 C 0.6380(3) 0.06091(13) 1.1456(2) 0.0402(8) Uani 1 1 d . . . C2 C 0.7215(3) 0.05283(13) 1.0766(2) 0.0407(8) Uani 1 1 d . . . C3 C 0.6535(3) 0.05946(13) 0.9816(2) 0.0406(8) Uani 1 1 d . . . C4 C 0.4994(3) 0.07344(13) 0.9614(2) 0.0421(8) Uani 1 1 d . . . C5 C 0.4233(3) 0.07915(13) 1.0338(2) 0.0419(8) Uani 1 1 d . . . C6 C 0.2590(3) 0.09180(14) 1.0138(2) 0.0492(9) Uani 1 1 d . . . H6A H 0.2162 0.0762 1.0636 0.059 Uiso 1 1 calc R . . H6B H 0.2111 0.0738 0.9556 0.059 Uiso 1 1 calc R . . C7 C 0.2220(4) 0.15173(17) 1.0057(3) 0.0729(12) Uani 1 1 d . . . H7A H 0.2590 0.1673 0.9536 0.087 Uiso 1 1 calc R . . H7B H 0.2725 0.1704 1.0627 0.087 Uiso 1 1 calc R . . C8 C 0.0524(4) 0.1615(2) 0.9900(4) 0.0990(16) Uani 1 1 d . . . H8A H 0.0027 0.1384 0.9382 0.119 Uiso 1 1 calc R . . H8B H 0.0193 0.1494 1.0457 0.119 Uiso 1 1 calc R . . C9 C 0.0019(5) 0.2172(2) 0.9701(5) 0.1119(19) Uani 1 1 d . . . H9 H 0.0465 0.2437 1.0132 0.134 Uiso 1 1 calc R . . C10 C -0.1006(5) 0.2350(2) 0.8977(4) 0.1027(17) Uani 1 1 d . . . C11 C -0.1513(6) 0.2932(2) 0.8840(5) 0.140(3) Uani 1 1 d . . . H11A H -0.1793 0.3075 0.9400 0.169 Uiso 1 1 calc R . . H11B H -0.0722 0.3162 0.8692 0.169 Uiso 1 1 calc R . . C12 C -0.2827(7) 0.2915(3) 0.8047(6) 0.157(3) Uani 1 1 d . . . H12A H -0.3751 0.2911 0.8278 0.188 Uiso 1 1 calc R . . H12B H -0.2836 0.3238 0.7654 0.188 Uiso 1 1 calc R . . C13 C -0.2720(8) 0.2418(3) 0.7505(6) 0.168(3) Uani 1 1 d . . . H13A H -0.2179 0.2491 0.7012 0.201 Uiso 1 1 calc R . . H13B H -0.3715 0.2279 0.7222 0.201 Uiso 1 1 calc R . . C14 C -0.1878(7) 0.2016(2) 0.8202(5) 0.148(3) Uani 1 1 d . . . H14A H -0.2573 0.1775 0.8429 0.178 Uiso 1 1 calc R . . H14B H -0.1210 0.1793 0.7918 0.178 Uiso 1 1 calc R . . C15 C 0.8744(4) 0.03671(14) 1.1034(2) 0.0471(9) Uani 1 1 d . . . C16 C 0.4197(3) 0.07813(15) 0.8671(2) 0.0493(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 N1 0.0322(14) 0.070(2) 0.0272(14) 0.0040(13) 0.0028(12) 0.0022(12) N2 0.0378(15) 0.097(2) 0.0277(15) 0.0021(15) 0.0032(13) 0.0084(14) N3 0.0410(17) 0.115(3) 0.053(2) 0.0062(19) 0.0043(15) 0.0095(17) N4 0.0420(15) 0.085(2) 0.0294(15) 0.0034(14) 0.0066(13) 0.0070(14) N5 0.068(2) 0.115(3) 0.0372(18) 0.0035(18) 0.0040(17) 0.0184(19) C1 0.0346(17) 0.055(2) 0.0278(17) -0.0006(15) 0.0005(14) 0.0003(14) C2 0.0306(15) 0.058(2) 0.0315(18) 0.0028(15) 0.0018(14) -0.0003(14) C3 0.0392(17) 0.051(2) 0.0306(18) -0.0005(15) 0.0066(15) -0.0012(14) C4 0.0372(16) 0.057(2) 0.0297(17) 0.0018(15) 0.0028(14) 0.0010(14) C5 0.0387(17) 0.050(2) 0.0348(19) 0.0032(15) 0.0035(15) 0.0019(14) C6 0.0376(17) 0.067(3) 0.0397(19) 0.0046(17) 0.0012(15) 0.0043(16) C7 0.047(2) 0.077(3) 0.092(3) 0.003(2) 0.009(2) 0.0092(19) C8 0.062(3) 0.089(4) 0.147(5) 0.018(3) 0.024(3) 0.025(2) C9 0.073(3) 0.088(4) 0.164(6) 0.003(4) 0.000(3) 0.011(3) C10 0.058(3) 0.089(4) 0.145(5) 0.015(3) -0.015(3) 0.001(3) C11 0.094(4) 0.098(5) 0.207(7) -0.006(4) -0.018(4) 0.013(3) C12 0.123(5) 0.106(5) 0.207(8) 0.004(5) -0.042(5) 0.026(4) C13 0.153(6) 0.144(7) 0.174(7) -0.001(6) -0.038(5) 0.027(5) C14 0.123(5) 0.098(4) 0.190(7) -0.020(4) -0.040(5) 0.022(4) C15 0.0392(18) 0.068(2) 0.0336(19) 0.0006(17) 0.0078(15) -0.0016(17) C16 0.0437(19) 0.070(3) 0.033(2) 0.0026(18) 0.0071(17) 0.0091(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 N1 C5 1.329(4) . ? N1 C1 1.351(4) . ? N2 C1 1.317(4) . ? N2 H2A 0.8600 . ? N2 H2B 0.8600 . ? N3 C15 1.140(4) . ? N4 C3 1.330(4) . ? N4 H4A 0.8600 . ? N4 H4B 0.8600 . ? N5 C16 1.137(4) . ? C1 C2 1.398(4) . ? C2 C3 1.399(4) . ? C2 C15 1.414(4) . ? C3 C4 1.408(4) . ? C4 C5 1.388(4) . ? C4 C16 1.413(4) . ? C5 C6 1.490(4) . ? C6 C7 1.492(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.527(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.436(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.320(6) . ? C9 H9 0.9300 . ? C10 C14 1.474(7) . ? C10 C11 1.488(7) . ? C11 C12 1.472(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.456(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.494(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 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 N1 C1 118.1(3) . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C3 N4 H4A 120.0 . . ? C3 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? N2 C1 N1 115.6(3) . . ? N2 C1 C2 122.2(3) . . ? N1 C1 C2 122.1(3) . . ? C1 C2 C3 120.2(3) . . ? C1 C2 C15 119.6(3) . . ? C3 C2 C15 120.2(3) . . ? N4 C3 C2 122.1(3) . . ? N4 C3 C4 121.7(3) . . ? C2 C3 C4 116.2(3) . . ? C5 C4 C3 120.1(3) . . ? C5 C4 C16 119.7(3) . . ? C3 C4 C16 120.1(3) . . ? N1 C5 C4 123.2(3) . . ? N1 C5 C6 115.8(3) . . ? C4 C5 C6 121.0(3) . . ? C5 C6 C7 114.6(3) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 111.5(3) . . ? C6 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C9 C8 C7 116.4(4) . . ? C9 C8 H8A 108.2 . . ? C7 C8 H8A 108.2 . . ? C9 C8 H8B 108.2 . . ? C7 C8 H8B 108.2 . . ? H8A C8 H8B 107.3 . . ? C10 C9 C8 127.5(5) . . ? C10 C9 H9 116.2 . . ? C8 C9 H9 116.2 . . ? C9 C10 C14 127.1(5) . . ? C9 C10 C11 124.3(5) . . ? C14 C10 C11 108.6(5) . . ? C12 C11 C10 104.7(5) . . ? C12 C11 H11A 110.8 . . ? C10 C11 H11A 110.8 . . ? C12 C11 H11B 110.8 . . ? C10 C11 H11B 110.8 . . ? H11A C11 H11B 108.9 . . ? C13 C12 C11 108.2(5) . . ? C13 C12 H12A 110.1 . . ? C11 C12 H12A 110.1 . . ? C13 C12 H12B 110.1 . . ? C11 C12 H12B 110.1 . . ? H12A C12 H12B 108.4 . . ? C12 C13 C14 104.9(6) . . ? C12 C13 H13A 110.8 . . ? C14 C13 H13A 110.8 . . ? C12 C13 H13B 110.8 . . ? C14 C13 H13B 110.8 . . ? H13A C13 H13B 108.8 . . ? C10 C14 C13 105.9(5) . . ? C10 C14 H14A 110.5 . . ? C13 C14 H14A 110.5 . . ? C10 C14 H14B 110.5 . . ? C13 C14 H14B 110.5 . . ? H14A C14 H14B 108.7 . . ? N3 C15 C2 179.1(4) . . ? N5 C16 C4 178.4(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 N1 C1 N2 178.6(3) . . . . ? C5 N1 C1 C2 -1.0(4) . . . . ? N2 C1 C2 C3 -177.6(3) . . . . ? N1 C1 C2 C3 2.1(5) . . . . ? N2 C1 C2 C15 3.9(5) . . . . ? N1 C1 C2 C15 -176.5(3) . . . . ? C1 C2 C3 N4 180.0(3) . . . . ? C15 C2 C3 N4 -1.5(5) . . . . ? C1 C2 C3 C4 -1.0(5) . . . . ? C15 C2 C3 C4 177.6(3) . . . . ? N4 C3 C4 C5 178.2(3) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? N4 C3 C4 C16 2.3(5) . . . . ? C2 C3 C4 C16 -176.7(3) . . . . ? C1 N1 C5 C4 -1.0(5) . . . . ? C1 N1 C5 C6 178.6(3) . . . . ? C3 C4 C5 N1 1.9(5) . . . . ? C16 C4 C5 N1 177.8(3) . . . . ? C3 C4 C5 C6 -177.6(3) . . . . ? C16 C4 C5 C6 -1.8(5) . . . . ? N1 C5 C6 C7 93.0(4) . . . . ? C4 C5 C6 C7 -87.4(4) . . . . ? C5 C6 C7 C8 -177.2(4) . . . . ? C6 C7 C8 C9 -172.9(5) . . . . ? C7 C8 C9 C10 125.7(6) . . . . ? C8 C9 C10 C14 0.2(10) . . . . ? C8 C9 C10 C11 177.5(6) . . . . ? C9 C10 C11 C12 -170.3(6) . . . . ? C14 C10 C11 C12 7.4(8) . . . . ? C10 C11 C12 C13 -22.6(8) . . . . ? C11 C12 C13 C14 28.8(8) . . . . ? C9 C10 C14 C13 -172.6(6) . . . . ? C11 C10 C14 C13 9.8(8) . . . . ? C12 C13 C14 C10 -23.4(8) . . . . ? C1 C2 C15 N3 76(26) . . . . ? C3 C2 C15 N3 -102(26) . . . . ? C5 C4 C16 N5 -94(13) . . . . ? C3 C4 C16 N5 82(13) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.313 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.049