# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1048 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Anita Cohen' 'Maxime D. Crozet' 'Pascal Rathelot' 'Patrice Vanelle' _publ_contact_author_name 'Maxime Crozet' _publ_contact_author_email maxime.crozet@pharmacie.univ-mrs.fr _publ_section_title ; An efficient aqueous microwave-assisted Suzuki-Miyaura cross-coupling reaction in thiazole series ; data_ac2154 _database_code_depnum_ccdc_archive 'CCDC 727244' _audit_creation_date 2009-03-23T14:17:00-00:00 _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 'C18 H16 F1 N1 O2 S2' _chemical_formula_sum 'C18 H16 F N O2 S2' _chemical_formula_weight 361.44 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1330(2) _cell_length_b 10.9315(3) _cell_length_c 11.3491(4) _cell_angle_alpha 111.001(1) _cell_angle_beta 103.328(2) _cell_angle_gamma 103.603(3) _cell_volume 858.68(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9942 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 28.16 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.33 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'Omega + Phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_unetI/netI 0.0491 _diffrn_reflns_number 9942 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 28.16 _diffrn_reflns_theta_full 28.16 _diffrn_measured_fraction_theta_full 0.954 _diffrn_measured_fraction_theta_max 0.954 _reflns_number_total 4023 _reflns_number_gt 3045 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _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^)+(0.0335P)^2^+3.4066P] 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_number_reflns 4023 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1008 _refine_ls_R_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.2201 _refine_ls_wR_factor_gt 0.2084 _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_restrained_S_all 1.098 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.463 _refine_diff_density_min -0.45 _refine_diff_density_rms 0.082 #----------------------------------------------------------------------------# # 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 '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 C7 C -0.5373(8) -0.0359(7) 0.2487(8) 0.086(2) Uani 1 1 d . . . H7A H -0.5586 -0.1238 0.2538 0.129 Uiso 1 1 calc R . . H7B H -0.5776 -0.0526 0.156 0.129 Uiso 1 1 calc R . . H7C H -0.6025 0.0146 0.2951 0.129 Uiso 1 1 calc R . . C9 C 0.1958(6) 0.5249(5) 0.7008(4) 0.0378(9) Uani 1 1 d . . . C1 C 0.0277(6) 0.2088(5) 0.4366(5) 0.0429(10) Uani 1 1 d . . . C2 C -0.0646(7) 0.1904(5) 0.3105(5) 0.0495(12) Uani 1 1 d . . . H2 H -0.0045 0.2318 0.2664 0.059 Uiso 1 1 calc R . . C3 C -0.2452(7) 0.1112(6) 0.2486(5) 0.0564(13) Uani 1 1 d . . . H3 H -0.3063 0.0991 0.1628 0.068 Uiso 1 1 calc R . . C4 C -0.3371(7) 0.0492(5) 0.3135(6) 0.0580(14) Uani 1 1 d . . . C5 C -0.2423(8) 0.0665(6) 0.4394(7) 0.0681(17) Uani 1 1 d . . . H5 H -0.3016 0.0241 0.4832 0.082 Uiso 1 1 calc R . . C6 C -0.0610(7) 0.1457(6) 0.5017(6) 0.0604(14) Uani 1 1 d . . . H6 H 0.0012 0.1566 0.5867 0.073 Uiso 1 1 calc R . . C8 C 0.2703(6) 0.4903(5) 0.5894(4) 0.0412(10) Uani 1 1 d . . . H8A H 0.3954 0.5508 0.6235 0.049 Uiso 1 1 calc R . . H8B H 0.2046 0.5098 0.5193 0.049 Uiso 1 1 calc R . . C10 C 0.2882(6) 0.6007(5) 0.8353(4) 0.0379(9) Uani 1 1 d . . . C11 C 0.4828(6) 0.6762(5) 0.9117(4) 0.0378(9) Uani 1 1 d . . . C12 C 0.5905(6) 0.7542(5) 0.8667(5) 0.0444(11) Uani 1 1 d . . . H12 H 0.5394 0.7592 0.7871 0.053 Uiso 1 1 calc R . . C13 C 0.7733(7) 0.8247(6) 0.9386(5) 0.0538(13) Uani 1 1 d . . . H13 H 0.8456 0.8763 0.9079 0.065 Uiso 1 1 calc R . . C14 C 0.8445(6) 0.8165(6) 1.0556(6) 0.0565(14) Uani 1 1 d . . . C15 C 0.7440(7) 0.7424(6) 1.1051(5) 0.0600(14) Uani 1 1 d . . . H15 H 0.7965 0.7389 1.1853 0.072 Uiso 1 1 calc R . . C16 C 0.5616(7) 0.6728(6) 1.0324(5) 0.0490(12) Uani 1 1 d . . . H16 H 0.4904 0.6228 1.065 0.059 Uiso 1 1 calc R . . C17 C -0.0410(6) 0.5024(5) 0.7677(5) 0.0451(11) Uani 1 1 d . . . C18 C -0.2337(6) 0.4563(7) 0.7589(6) 0.0607(15) Uani 1 1 d . . . H18A H -0.3031 0.485 0.7002 0.091 Uiso 1 1 calc R . . H18B H -0.2408 0.498 0.8469 0.091 Uiso 1 1 calc R . . H18C H -0.2807 0.3563 0.724 0.091 Uiso 1 1 calc R . . F1 F 1.0248(4) 0.8857(4) 1.1271(4) 0.0883(13) Uani 1 1 d . . . N1 N 0.0104(5) 0.4701(4) 0.6638(4) 0.0420(9) Uani 1 1 d . . . O1 O 0.3387(5) 0.3006(4) 0.4150(4) 0.0658(11) Uani 1 1 d . . . O2 O 0.3332(5) 0.2795(4) 0.6250(4) 0.0593(10) Uani 1 1 d . . . S1 S 0.13473(16) 0.60358(15) 0.91902(12) 0.0487(4) Uani 1 1 d . . . S2 S 0.25788(15) 0.31253(14) 0.51726(12) 0.0454(3) 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 C7 0.044(3) 0.062(4) 0.116(6) 0.026(4) 0.005(3) 0.002(3) C9 0.029(2) 0.044(2) 0.037(2) 0.0180(19) 0.0117(17) 0.0080(17) C1 0.035(2) 0.039(2) 0.045(2) 0.012(2) 0.0152(19) 0.0060(18) C2 0.048(3) 0.048(3) 0.047(3) 0.019(2) 0.015(2) 0.011(2) C3 0.052(3) 0.052(3) 0.050(3) 0.016(2) 0.004(2) 0.016(2) C4 0.040(3) 0.040(3) 0.074(4) 0.013(3) 0.011(3) 0.007(2) C5 0.052(3) 0.064(4) 0.079(4) 0.030(3) 0.025(3) 0.002(3) C6 0.047(3) 0.068(4) 0.056(3) 0.029(3) 0.013(2) 0.004(3) C8 0.031(2) 0.045(2) 0.037(2) 0.015(2) 0.0119(17) 0.0021(18) C10 0.031(2) 0.045(2) 0.039(2) 0.0187(19) 0.0156(17) 0.0110(18) C11 0.032(2) 0.042(2) 0.036(2) 0.0151(19) 0.0115(17) 0.0101(18) C12 0.037(2) 0.047(3) 0.045(3) 0.020(2) 0.0146(19) 0.009(2) C13 0.036(2) 0.052(3) 0.058(3) 0.014(2) 0.018(2) 0.004(2) C14 0.029(2) 0.059(3) 0.055(3) 0.010(3) 0.004(2) 0.005(2) C15 0.045(3) 0.074(4) 0.044(3) 0.019(3) -0.001(2) 0.016(3) C16 0.039(2) 0.059(3) 0.041(3) 0.020(2) 0.010(2) 0.011(2) C17 0.036(2) 0.053(3) 0.047(3) 0.024(2) 0.016(2) 0.012(2) C18 0.031(2) 0.084(4) 0.071(4) 0.037(3) 0.023(2) 0.018(3) F1 0.0344(17) 0.097(3) 0.085(3) 0.019(2) -0.0037(16) -0.0029(17) N1 0.0258(17) 0.052(2) 0.046(2) 0.0214(18) 0.0118(15) 0.0107(16) O1 0.052(2) 0.074(3) 0.063(2) 0.015(2) 0.0373(19) 0.0124(19) O2 0.0404(19) 0.070(2) 0.071(2) 0.038(2) 0.0106(17) 0.0205(17) S1 0.0352(6) 0.0652(8) 0.0430(6) 0.0202(6) 0.0191(5) 0.0130(5) S2 0.0308(6) 0.0528(7) 0.0474(7) 0.0175(6) 0.0163(5) 0.0100(5) #----------------------------------------------------------------------------# # 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 C7 C4 1.518(7) . ? C7 H7A 0.96 . ? C7 H7B 0.96 . ? C7 H7C 0.96 . ? C9 C10 1.361(6) . ? C9 N1 1.382(5) . ? C9 C8 1.493(6) . ? C1 C2 1.372(7) . ? C1 C6 1.385(7) . ? C1 S2 1.759(5) . ? C2 C3 1.375(7) . ? C2 H2 0.93 . ? C3 C4 1.391(8) . ? C3 H3 0.93 . ? C4 C5 1.380(9) . ? C5 C6 1.379(7) . ? C5 H5 0.93 . ? C6 H6 0.93 . ? C8 S2 1.785(5) . ? C8 H8A 0.97 . ? C8 H8B 0.97 . ? C10 C11 1.475(6) . ? C10 S1 1.734(4) . ? C11 C12 1.387(6) . ? C11 C16 1.390(6) . ? C12 C13 1.386(6) . ? C12 H12 0.93 . ? C13 C14 1.365(8) . ? C13 H13 0.93 . ? C14 C15 1.366(8) . ? C14 F1 1.368(5) . ? C15 C16 1.384(7) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? C17 N1 1.299(6) . ? C17 C18 1.497(6) . ? C17 S1 1.726(5) . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? O1 S2 1.442(4) . ? O2 S2 1.441(4) . ? 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 C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C10 C9 N1 115.7(4) . . ? C10 C9 C8 128.0(4) . . ? N1 C9 C8 116.3(4) . . ? C2 C1 C6 119.8(5) . . ? C2 C1 S2 120.7(4) . . ? C6 C1 S2 119.6(4) . . ? C1 C2 C3 120.6(5) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C2 C3 C4 120.4(5) . . ? C2 C3 H3 119.8 . . ? C4 C3 H3 119.8 . . ? C5 C4 C3 118.6(5) . . ? C5 C4 C7 120.0(6) . . ? C3 C4 C7 121.4(6) . . ? C6 C5 C4 121.2(6) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C1 119.5(5) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C9 C8 S2 113.7(3) . . ? C9 C8 H8A 108.8 . . ? S2 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? S2 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? C9 C10 C11 131.3(4) . . ? C9 C10 S1 108.6(3) . . ? C11 C10 S1 120.1(3) . . ? C12 C11 C16 118.4(4) . . ? C12 C11 C10 121.1(4) . . ? C16 C11 C10 120.5(4) . . ? C13 C12 C11 121.0(5) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 118.3(5) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C13 C14 C15 123.1(5) . . ? C13 C14 F1 118.6(5) . . ? C15 C14 F1 118.3(5) . . ? C14 C15 C16 118.0(5) . . ? C14 C15 H15 121 . . ? C16 C15 H15 121 . . ? C15 C16 C11 121.3(5) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? N1 C17 C18 123.8(5) . . ? N1 C17 S1 113.7(3) . . ? C18 C17 S1 122.5(4) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 N1 C9 111.8(4) . . ? C17 S1 C10 90.3(2) . . ? O2 S2 O1 119.0(3) . . ? O2 S2 C1 108.8(2) . . ? O1 S2 C1 107.9(2) . . ? O2 S2 C8 108.2(2) . . ? O1 S2 C8 105.4(2) . . ? C1 S2 C8 106.9(2) . . ?