data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Changtao Qian.' 'Min-Zhi Deng.' 'Li-Yan Fan.' 'Feifeng Gao.' 'Wei-Hua Jiang.' _publ_contact_author_name 'Changtao Qian' _publ_contact_author_email QIANCT@MAIL.SIOC.AC.CN _publ_section_title ; A Simple, Efficient Pd-Catalyzed Synthesis of N-sulfonyl-imines from Organoboronic Acid and Tosylbenzimidoyl Chlorides ; # Attachment 'cd26273.cif' data_cd26273 _database_code_depnum_ccdc_archive 'CCDC 679167' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N O2 S' _chemical_formula_weight 287.37 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.6787(9) _cell_length_b 13.9781(15) _cell_length_c 12.3242(13) _cell_angle_alpha 90.00 _cell_angle_beta 99.664(2) _cell_angle_gamma 90.00 _cell_volume 1473.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3342 _cell_measurement_theta_min 4.761 _cell_measurement_theta_max 53.719 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.496 _exptl_crystal_size_mid 0.415 _exptl_crystal_size_min 0.347 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.73594 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 8462 _diffrn_reflns_av_R_equivalents 0.0998 _diffrn_reflns_av_sigmaI/netI 0.0658 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3199 _reflns_number_gt 2392 _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^)+(0.0846P)^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 3199 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.1425 _refine_ls_wR_factor_gt 0.1359 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _refine_ls_shift/su_max 0.000 _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 S1 S 0.70189(5) 0.12908(3) 0.68264(4) 0.05215(19) Uani 1 1 d . . . O1 O 0.82545(17) 0.17497(10) 0.75579(12) 0.0721(4) Uani 1 1 d . . . O2 O 0.61536(19) 0.18363(10) 0.59503(11) 0.0727(4) Uani 1 1 d . . . N1 N 0.57779(16) 0.07667(10) 0.75177(11) 0.0473(3) Uani 1 1 d . . . C1 C 0.3540(2) -0.02522(13) 0.83880(15) 0.0538(4) Uani 1 1 d . . . H1 H 0.3919 -0.0510 0.7789 0.065 Uiso 1 1 calc R . . C2 C 0.2599(2) -0.07962(14) 0.89330(17) 0.0618(5) Uani 1 1 d . . . H2 H 0.2356 -0.1421 0.8708 0.074 Uiso 1 1 calc R . . C3 C 0.2011(2) -0.04192(15) 0.98151(16) 0.0591(5) Uani 1 1 d . . . H3 H 0.1370 -0.0788 1.0183 0.071 Uiso 1 1 calc R . . C4 C 0.2375(2) 0.04955(15) 1.01427(16) 0.0638(5) Uani 1 1 d . . . H4 H 0.1976 0.0752 1.0734 0.077 Uiso 1 1 calc R . . C5 C 0.3330(2) 0.10438(13) 0.96039(15) 0.0561(5) Uani 1 1 d . . . H5 H 0.3571 0.1667 0.9838 0.067 Uiso 1 1 calc R . . C6 C 0.39360(18) 0.06783(11) 0.87175(12) 0.0429(4) Uani 1 1 d . . . C7 C 0.50276(19) 0.12406(11) 0.81540(12) 0.0434(4) Uani 1 1 d . . . C8 C 0.5115(2) 0.23092(12) 0.83421(15) 0.0577(5) Uani 1 1 d . . . H8A H 0.5202 0.2440 0.9123 0.069 Uiso 1 1 calc R . . H8B H 0.6043 0.2559 0.8099 0.069 Uiso 1 1 calc R . . C9 C 0.3699(3) 0.28060(16) 0.7732(2) 0.0863(7) Uani 1 1 d . . . H9A H 0.3670 0.2733 0.6954 0.129 Uiso 1 1 calc R . . H9B H 0.3744 0.3474 0.7917 0.129 Uiso 1 1 calc R . . H9C H 0.2775 0.2529 0.7934 0.129 Uiso 1 1 calc R . . C10 C 0.7818(2) 0.02936(13) 0.62584(14) 0.0479(4) Uani 1 1 d . . . C11 C 0.7207(2) -0.00175(15) 0.52205(15) 0.0609(5) Uani 1 1 d . . . H11 H 0.6355 0.0294 0.4812 0.073 Uiso 1 1 calc R . . C12 C 0.7864(2) -0.07952(16) 0.47872(17) 0.0663(5) Uani 1 1 d . . . H12 H 0.7442 -0.1003 0.4083 0.080 Uiso 1 1 calc R . . C13 C 0.9122(2) -0.12721(13) 0.53634(17) 0.0568(5) Uani 1 1 d . . . C14 C 0.9711(2) -0.09485(15) 0.64091(18) 0.0643(5) Uani 1 1 d . . . H14 H 1.0555 -0.1266 0.6820 0.077 Uiso 1 1 calc R . . C15 C 0.9086(2) -0.01733(15) 0.68565(15) 0.0601(5) Uani 1 1 d . . . H15 H 0.9512 0.0038 0.7559 0.072 Uiso 1 1 calc R . . C16 C 0.9841(3) -0.21283(16) 0.4900(2) 0.0794(7) Uani 1 1 d . . . H16A H 0.9543 -0.2699 0.5244 0.119 Uiso 1 1 calc R . . H16B H 1.0959 -0.2068 0.5039 0.119 Uiso 1 1 calc R . . H16C H 0.9480 -0.2163 0.4121 0.119 Uiso 1 1 calc R . . 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 S1 0.0673(3) 0.0436(3) 0.0493(3) 0.00107(18) 0.0209(2) -0.00358(19) O1 0.0735(9) 0.0702(9) 0.0769(9) -0.0212(7) 0.0253(7) -0.0205(7) O2 0.1041(11) 0.0571(8) 0.0621(9) 0.0195(6) 0.0288(8) 0.0168(7) N1 0.0572(8) 0.0422(7) 0.0447(8) 0.0019(6) 0.0147(6) 0.0009(6) C1 0.0607(10) 0.0460(9) 0.0564(11) -0.0042(8) 0.0148(8) -0.0010(8) C2 0.0620(11) 0.0459(10) 0.0768(14) 0.0016(9) 0.0094(10) -0.0075(8) C3 0.0530(10) 0.0609(11) 0.0644(12) 0.0159(9) 0.0131(9) -0.0017(9) C4 0.0757(12) 0.0643(12) 0.0572(12) 0.0034(9) 0.0278(10) 0.0038(10) C5 0.0712(12) 0.0483(9) 0.0522(11) -0.0009(8) 0.0199(9) 0.0006(9) C6 0.0471(8) 0.0418(8) 0.0386(8) 0.0032(7) 0.0039(7) 0.0054(7) C7 0.0516(9) 0.0405(9) 0.0367(9) 0.0022(6) 0.0038(7) 0.0018(7) C8 0.0784(12) 0.0412(9) 0.0588(11) -0.0094(8) 0.0274(9) -0.0081(9) C9 0.1159(19) 0.0514(11) 0.0988(17) 0.0104(12) 0.0388(15) 0.0249(13) C10 0.0545(9) 0.0485(9) 0.0438(9) 0.0023(7) 0.0172(7) -0.0027(8) C11 0.0641(11) 0.0665(12) 0.0506(11) -0.0028(9) 0.0052(9) 0.0064(9) C12 0.0763(12) 0.0696(13) 0.0528(11) -0.0150(10) 0.0100(10) -0.0030(11) C13 0.0579(10) 0.0488(10) 0.0694(13) -0.0017(8) 0.0266(10) -0.0069(8) C14 0.0592(11) 0.0654(12) 0.0671(13) 0.0004(10) 0.0077(9) 0.0067(10) C15 0.0648(11) 0.0660(12) 0.0478(10) -0.0018(9) 0.0050(9) 0.0035(9) C16 0.0827(14) 0.0583(12) 0.1058(18) -0.0139(12) 0.0403(13) -0.0033(11) _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 S1 O2 1.4280(14) . ? S1 O1 1.4316(15) . ? S1 N1 1.6525(13) . ? S1 C10 1.7543(18) . ? N1 C7 1.284(2) . ? C1 C2 1.371(2) . ? C1 C6 1.388(2) . ? C1 H1 0.9300 . ? C2 C3 1.381(3) . ? C2 H2 0.9300 . ? C3 C4 1.362(3) . ? C3 H3 0.9300 . ? C4 C5 1.379(2) . ? C4 H4 0.9300 . ? C5 C6 1.387(2) . ? C5 H5 0.9300 . ? C6 C7 1.489(2) . ? C7 C8 1.512(2) . ? C8 C9 1.499(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.371(3) . ? C10 C15 1.381(3) . ? C11 C12 1.376(3) . ? C11 H11 0.9300 . ? C12 C13 1.371(3) . ? C12 H12 0.9300 . ? C13 C14 1.380(3) . ? C13 C16 1.506(3) . ? C14 C15 1.369(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 O2 S1 O1 118.69(10) . . ? O2 S1 N1 108.73(8) . . ? O1 S1 N1 110.99(8) . . ? O2 S1 C10 108.40(8) . . ? O1 S1 C10 107.61(8) . . ? N1 S1 C10 100.90(7) . . ? C7 N1 S1 121.82(11) . . ? C2 C1 C6 120.97(17) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C1 C2 C3 120.21(17) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 119.60(17) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.48(18) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.85(18) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 117.87(16) . . ? C5 C6 C7 121.86(15) . . ? C1 C6 C7 120.23(15) . . ? N1 C7 C6 116.10(14) . . ? N1 C7 C8 125.87(15) . . ? C6 C7 C8 118.00(14) . . ? C9 C8 C7 111.40(16) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 119.80(17) . . ? C11 C10 S1 120.49(14) . . ? C15 C10 S1 119.71(14) . . ? C10 C11 C12 119.48(18) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C13 C12 C11 121.92(18) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C14 117.51(18) . . ? C12 C13 C16 122.3(2) . . ? C14 C13 C16 120.17(19) . . ? C15 C14 C13 121.73(18) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C14 C15 C10 119.56(18) . . ? C14 C15 H15 120.2 . . ? C10 C15 H15 120.2 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 O2 S1 N1 C7 -72.70(15) . . . . ? O1 S1 N1 C7 59.60(15) . . . . ? C10 S1 N1 C7 173.42(14) . . . . ? C6 C1 C2 C3 0.8(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 0.2(3) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C4 C5 C6 C7 -177.19(16) . . . . ? C2 C1 C6 C5 -1.0(3) . . . . ? C2 C1 C6 C7 176.73(15) . . . . ? S1 N1 C7 C6 179.43(10) . . . . ? S1 N1 C7 C8 1.8(2) . . . . ? C5 C6 C7 N1 165.04(16) . . . . ? C1 C6 C7 N1 -12.5(2) . . . . ? C5 C6 C7 C8 -17.1(2) . . . . ? C1 C6 C7 C8 165.27(17) . . . . ? N1 C7 C8 C9 103.5(2) . . . . ? C6 C7 C8 C9 -74.1(2) . . . . ? O2 S1 C10 C11 -20.00(17) . . . . ? O1 S1 C10 C11 -149.53(15) . . . . ? N1 S1 C10 C11 94.12(15) . . . . ? O2 S1 C10 C15 159.15(15) . . . . ? O1 S1 C10 C15 29.62(17) . . . . ? N1 S1 C10 C15 -86.73(15) . . . . ? C15 C10 C11 C12 0.2(3) . . . . ? S1 C10 C11 C12 179.31(15) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C11 C12 C13 C16 179.5(2) . . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C16 C13 C14 C15 -179.95(19) . . . . ? C13 C14 C15 C10 0.9(3) . . . . ? C11 C10 C15 C14 -0.6(3) . . . . ? S1 C10 C15 C14 -179.72(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.346 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.057