Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_1 _database_code_CSD 177912 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Deniaud, David' 'Landreau, Cyrille' 'Meslin, Jean-Claude' 'Reliquet, Alan' _publ_contact_author_name 'Dr David Deniaud' _publ_contact_author_address ; Laboratoire de synthese organique Faculté des Sciences et des Techniq Nantes 44322 GHANA ; _publ_contact_author_email 'DAVID.DENIAUD@CHIMIE.UNIV-NANTES.FR' _publ_section_title ; Efficient regioselective synthesis of triheterocyclic compounds: imidazo[2,1-b]benzothiazoles, pyrimido[2,1-b]benzothiazolones and pyrimido[2,1-b]benzothiazoles. ; _cell_length_a 14.4765(18) _cell_length_b 11.1064(9) _cell_length_c 14.5268(18) _cell_angle_alpha 90 _cell_angle_beta 150.686(15) _cell_angle_gamma 90 _cell_volume 1143.5(6) _cell_measurement_pressure ? _cell_measurement_radiation ? _cell_measurement_reflns_used ? _cell_measurement_temperature ? _cell_measurement_theta_max ? _cell_measurement_theta_min ? _cell_measurement_wavelength ? _cell_formula_units_Z 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,1/2-z 3 -x,-y,-z 4 x,1/2-y,1/2+z loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source _atom_type_scat_versus_stol_list S 0 0.000 0.000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.1' ; stol 0.00 0.05 0.10 0.15 0.20 0.25 0.30 0.35 0.40 f 16.000 15.484 14.177 12.583 11.109 9.927 9.039 8.376 7.856 stol 0.45 0.50 0.55 0.60 0.65 0.70 0.75 0.80 0.85 f 7.417 7.017 6.633 6.254 5.877 5.505 5.141 4.790 4.454 stol 0.90 0.95 1.00 1.05 1.10 1.15 1.20 1.25 1.30 f 4.138 3.842 3.570 3.320 3.092 2.885 2.699 2.533 2.384 stol 1.35 1.40 1.45 1.50 1.55 1.60 1.65 1.70 1.75 f 2.251 2.133 2.028 1.935 1.853 1.779 1.713 1.655 1.604 ; N 0 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.1' ; stol 0.00 0.05 0.10 0.15 0.20 0.25 0.30 0.35 0.40 f 7.000 6.776 6.180 5.385 4.563 3.825 3.219 2.747 2.393 stol 0.45 0.50 0.55 0.60 0.65 0.70 0.75 0.80 0.85 f 2.132 1.942 1.802 1.697 1.616 1.551 1.496 1.445 1.398 stol 0.90 0.95 1.00 1.05 1.10 1.15 1.20 1.25 1.30 f 1.353 1.309 1.265 1.221 1.177 1.133 1.090 1.047 1.004 stol 1.35 1.40 1.45 1.50 1.55 1.60 1.65 1.70 1.75 f 0.962 0.921 0.882 0.843 0.805 0.769 0.734 0.700 0.667 ; O 0 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.1' ; stol 0.00 0.05 0.10 0.15 0.20 0.25 0.30 0.35 0.40 f 8.000 7.798 7.245 6.472 5.623 4.808 4.089 3.489 3.006 stol 0.45 0.50 0.55 0.60 0.65 0.70 0.75 0.80 0.85 f 2.629 2.338 2.115 1.946 1.816 1.714 1.635 1.568 1.512 stol 0.90 0.95 1.00 1.05 1.10 1.15 1.20 1.25 1.30 f 1.463 1.419 1.377 1.337 1.298 1.259 1.221 1.183 1.145 stol 1.35 1.40 1.45 1.50 1.55 1.60 1.65 1.70 1.75 f 1.107 1.070 1.033 0.997 0.961 0.926 0.891 0.857 0.824 ; C 0 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.1' ; stol 0.00 0.05 0.10 0.15 0.20 0.25 0.30 0.35 0.40 f 6.000 5.749 5.107 4.311 3.560 2.949 2.494 2.171 1.948 stol 0.45 0.50 0.55 0.60 0.65 0.70 0.75 0.80 0.85 f 1.794 1.685 1.603 1.537 1.479 1.426 1.374 1.322 1.271 stol 0.90 0.95 1.00 1.05 1.10 1.15 1.20 1.25 1.30 f 1.219 1.166 1.114 1.063 1.012 0.962 0.914 0.867 0.822 stol 1.35 1.40 1.45 1.50 1.55 1.60 1.65 1.70 1.75 f 0.778 0.736 0.697 0.659 0.622 0.588 0.556 0.525 0.495 ; H 0 0.000 0.000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.1' ; stol 0.00 0.05 0.10 0.15 0.20 0.25 0.30 0.35 0.40 f 1.000 0.960 0.854 0.713 0.568 0.438 0.331 0.248 0.184 stol 0.45 0.50 0.55 0.60 0.65 0.70 0.75 0.80 0.85 f 0.138 0.103 0.078 0.060 0.046 0.036 0.028 0.022 0.018 stol 0.90 0.95 1.00 1.05 1.10 1.15 1.20 1.25 1.30 f 0.014 0.011 0.009 0.007 0.006 0.005 0.004 0.004 0.003 stol 1.35 1.40 1.45 1.50 1.55 1.60 1.65 1.70 1.75 f 0.003 0.002 0.002 0.002 0.002 0.002 0.001 0.001 0.000 ; _chemical_formula_sum 'C12 H10 N2 O2 S' _chemical_formula_moiety 'C12 H10 N2 O2 S' _chemical_formula_weight 246.3 _exptl_crystal_colour ? _exptl_crystal_description ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.43 _exptl_crystal_density_meas ? _exptl_crystal_density_meas_temp ? _exptl_crystal_density_method ? _exptl_crystal_F_000 512 _exptl_absorpt_correction_type none _exptl_absorpt_coefficient_mu 0.273 _exptl_absorpt_correction_T_min 1.000 _exptl_absorpt_correction_T_max 1.000 _diffrn_measurement_device_type 'Nonius CAD4F and Stoe IPDS' _diffrn_measurement_method ? _diffrn_radiation_probe 'X-ray' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_standards_number 3 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 60 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min -20 _reflns_limit_h_max 0 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min -9 _reflns_limit_l_max 20 _diffrn_reflns_number 13223 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 29.99 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.1958 _reflns_observed_criterion 2 _reflns_number_total 3337 _reflns_number_observed 999 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w=1/(\s^2^(I)+0.001024I^2^)' _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_gt 0.0681 _refine_ls_R_factor_all 0.2261 _refine_ls_wR_factor_ref 0.1128 _refine_ls_number_reflns 3337 _refine_ls_number_parameters 155 _refine_ls_goodness_of_fit_ref 0.85 _refine_ls_goodness_of_fit_obs 0.99 _refine_ls_shift/su_max 0.0001 _refine_ls_shift/su_mean 0.0000 _refine_diff_density_max 0.40 _refine_diff_density_min -0.27 _refine_ls_extinction_method 'B-C type 1 Gaussian isotropic' _refine_ls_extinction_coef 0.13(3) loop_ _atom_site_label _atom_site_type_symbol _atom_site_adp_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity _atom_site_occupancy N1 N Uani 0.1779(4) 0.6359(3) 0.3752(4) 0.062(7) 4 1 C2 C Uani 0.2737(5) 0.7006(3) 0.3931(5) 0.058(8) 4 1 C3 C Uani 0.3021(4) 0.6379(3) 0.3385(4) 0.043(6) 4 1 N4 N Uani 0.2194(3) 0.5261(3) 0.2830(3) 0.042(5) 4 1 C4a C Uani 0.1861(4) 0.4148(3) 0.2102(4) 0.041(6) 4 1 C5 C Uani 0.2384(4) 0.3768(3) 0.1691(4) 0.048(7) 4 1 C6 C Uani 0.1899(5) 0.2627(3) 0.0997(5) 0.060(8) 4 1 C7 C Uani 0.0903(5) 0.1867(3) 0.0706(5) 0.065(8) 4 1 C8 C Uani 0.0369(5) 0.2232(3) 0.1105(5) 0.059(7) 4 1 C8a C Uani 0.0856(4) 0.3380(3) 0.1812(4) 0.048(7) 4 1 S9 S Uani 0.03373(13) 0.40270(9) 0.24271(13) 0.060(2) 4 1 C9a C Uani 0.1486(5) 0.5326(3) 0.3086(5) 0.050(7) 4 1 C10 C Uani 0.3941(4) 0.6755(3) 0.3340(4) 0.047(7) 4 1 C11 C Uani 0.5207(5) 0.8461(3) 0.3681(5) 0.063(8) 4 1 C12 C Uani 0.5246(8) 0.9752(4) 0.3832(8) 0.118(17) 4 1 O1 O Uani 0.4311(3) 0.6146(2) 0.3009(3) 0.066(6) 4 1 O2 O Uani 0.4339(3) 0.7931(2) 0.3733(3) 0.059(5) 4 1 H2 H Uiso 0.3181 0.783512 0.4404 0.0577 4 1 H5 H Uiso 0.3098 0.429974 0.1893 0.0479 4 1 H6 H Uiso 0.2281 0.235367 0.0714 0.0601 4 1 H7 H Uiso 0.0554 0.105788 0.0190 0.0650 4 1 H8 H Uiso -0.0331 0.168862 0.0905 0.0586 4 1 H11a H Uiso 0.4475 0.824571 0.2496 0.0625 4 1 H11b H Uiso 0.6498 0.815733 0.4738 0.0625 4 1 H12a H Uiso 0.3949 1.0033 0.2798 0.1183 4 1 H12b H Uiso 0.5789 1.015269 0.3764 0.1183 4 1 H12c H Uiso 0.6003 0.993855 0.5035 0.1183 4 1 loop_ _atom_site_aniso_label _atom_site_aniso_type_symbol _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 N1 N 0.078(2) 0.066(2) 0.080(2) 0.0051(17) 0.074(2) 0.0016(18) C2 C 0.070(3) 0.055(2) 0.072(3) 0.003(2) 0.065(2) 0.001(2) C3 C 0.046(2) 0.047(2) 0.046(2) 0.0058(18) 0.042(2) 0.0078(17) N4 N 0.0434(17) 0.0520(18) 0.0406(17) 0.0087(15) 0.0380(16) 0.0092(15) C4a C 0.0368(19) 0.054(2) 0.0349(19) 0.0048(18) 0.0316(18) 0.0073(18) C5 C 0.049(2) 0.054(2) 0.052(2) -0.0033(18) 0.046(2) -0.0015(18) C6 C 0.067(3) 0.065(3) 0.068(3) -0.010(2) 0.061(2) -0.014(2) C7 C 0.073(3) 0.058(3) 0.073(3) -0.012(2) 0.065(3) -0.012(2) C8 C 0.056(2) 0.065(3) 0.060(2) -0.006(2) 0.051(2) 0.002(2) C8a C 0.044(2) 0.060(2) 0.044(2) 0.0065(19) 0.039(2) 0.0094(19) S9 S 0.0666(6) 0.0725(7) 0.0708(7) 0.0028(6) 0.0642(6) 0.0072(6) C9a C 0.058(2) 0.059(2) 0.061(2) 0.009(2) 0.056(2) 0.012(2) C10 C 0.044(2) 0.050(2) 0.044(2) 0.0034(19) 0.038(2) 0.0042(18) C11 C 0.068(3) 0.066(3) 0.078(3) 0.000(2) 0.067(3) 0.005(2) C12 C 0.192(5) 0.066(3) 0.223(6) -0.015(4) 0.199(6) -0.009(4) O1 O 0.0876(19) 0.0595(16) 0.1022(20) -0.0059(14) 0.0897(19) -0.0106(15) O2 O 0.0734(17) 0.0536(16) 0.0834(18) -0.0033(14) 0.0732(17) -0.0020(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N1 C2 1.371(10) . . N1 C9a 1.310(7) . . C2 C3 1.361(11) . . C2 H2 0.982 . . C3 N4 1.393(5) . . C3 C10 1.451(11) . . N4 C4a 1.411(6) . . N4 C9a 1.363(12) . . C4a C5 1.377(11) . . C4a C8a 1.398(9) . . C5 C6 1.371(5) . . C5 H5 0.987 . . C6 C7 1.381(11) . . C6 H6 0.982 . . C7 C8 1.371(14) . . C7 H7 0.982 . . C8 C8a 1.384(5) . . C8 H8 0.981 . . C8a S9 1.746(8) . . S9 C9a 1.729(5) . . C10 O1 1.194(9) . . C10 O2 1.338(4) . . C11 C12 1.444(6) . . C11 O2 1.448(10) . . C11 H11a 0.981 . . C11 H11b 0.980 . . C12 H12a 0.980 . . C12 H12b 0.980 . . C12 H12c 0.979 . . 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_2 _geom_angle_site_symmetry_3 C2 N1 C9a 102.8(7) . . . N1 C2 C3 113.0(4) . . . N1 C2 H2 124.1 . . . C3 C2 H2 122.8 . . . C2 C3 N4 104.4(6) . . . C2 C3 C10 129.4(4) . . . N4 C3 C10 126.1(5) . . . C3 N4 C4a 140.7(6) . . . C3 N4 C9a 105.4(4) . . . C4a N4 C9a 113.8(4) . . . N4 C4a C5 129.5(5) . . . N4 C4a C8a 110.3(6) . . . C5 C4a C8a 120.2(4) . . . C4a C5 C6 118.6(6) . . . C4a C5 H5 121.1 . . . C6 C5 H5 120.3 . . . C5 C6 C7 121.2(8) . . . C5 C6 H6 118.6 . . . C7 C6 H6 120.1 . . . C6 C7 C8 120.9(4) . . . C6 C7 H7 119.9 . . . C8 C7 H7 119.3 . . . C7 C8 C8a 118.4(6) . . . C7 C8 H8 120.7 . . . C8a C8 H8 120.8 . . . C4a C8a C8 120.6(7) . . . C4a C8a S9 113.2(3) . . . C8 C8a S9 126.2(6) . . . C8a S9 C9a 89.5(3) . . . N1 C9a N4 114.3(6) . . . N1 C9a S9 132.5(8) . . . N4 C9a S9 113.2(4) . . . C3 C10 O1 127.4(4) . . . C3 C10 O2 109.4(5) . . . O1 C10 O2 123.2(6) . . . C12 C11 O2 108.4(8) . . . C12 C11 H11a 110.4 . . . C12 C11 H11b 109.6 . . . O2 C11 H11a 109.5 . . . O2 C11 H11b 109.5 . . . H11a C11 H11b 109.4 . . . C11 C12 H12a 108.3 . . . C11 C12 H12b 111.4 . . . C11 C12 H12c 108.4 . . . H12a C12 H12b 109.5 . . . H12a C12 H12c 109.6 . . . H12b C12 H12c 109.6 . . . C10 O2 C11 116.4(5) . . .