#Supplementary Material (ESI) for Chemical Communications #This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Lee, Hyeon-Kyu' _publ_contact_author_email leehk@krict.re.kr _publ_section_title ; Dynamic Kinetic Resolution in the Stereoselective Synthesis of 4,5-Diaryl Cyclic Sulfamidates by Using Chiral Rhodium-Catalyzed Asymmetric Transfer Hydrogenation ; loop_ _publ_author_name J.Han S.Kang H.-K.Lee # Attachment '- 7a.cif' data_20100309_0m _database_code_depnum_ccdc_archive 'CCDC 803456' #TrackingRef '- 7a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N O3 S' _chemical_formula_weight 275.31 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 5.72190(10) _cell_length_b 14.5983(4) _cell_length_c 15.3184(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1279.55(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2091 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 24.38 _exptl_crystal_description plate _exptl_crystal_colour silver _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9226 _exptl_absorpt_correction_T_max 0.9873 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7449 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3142 _reflns_number_gt 2408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0542P)^2^+0.0969P] 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 refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(10) _refine_ls_number_reflns 3142 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.1077 _refine_ls_wR_factor_gt 0.0979 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C1 C 0.2171(4) 0.23411(17) 0.17404(15) 0.0436(5) Uani 1 1 d . . . H1A H 0.3171 0.2678 0.1332 0.052 Uiso 1 1 calc R . . C2 C 0.2958(4) 0.13274(16) 0.17582(14) 0.0448(6) Uani 1 1 d . . . H2A H 0.4660 0.1303 0.1689 0.054 Uiso 1 1 calc R . . O3 O 0.1865(4) 0.09159(12) 0.09864(10) 0.0555(5) Uani 1 1 d . . . S4 S -0.00388(11) 0.15438(4) 0.05563(3) 0.04512(16) Uani 1 1 d . . . N5 N -0.0197(4) 0.22675(13) 0.13619(11) 0.0459(5) Uani 1 1 d . . . H5A H -0.1427 0.2553 0.1535 0.055 Uiso 1 1 calc R . . O6 O 0.0925(3) 0.19362(13) -0.02173(10) 0.0560(5) Uani 1 1 d . . . O7 O -0.2125(3) 0.10414(13) 0.04631(13) 0.0650(5) Uani 1 1 d . . . C8 C 0.2241(4) 0.28157(16) 0.26157(15) 0.0422(5) Uani 1 1 d . . . C9 C 0.0504(4) 0.27067(18) 0.32382(15) 0.0493(6) Uani 1 1 d . . . H9A H -0.0818 0.2361 0.3109 0.059 Uiso 1 1 calc R . . C10 C 0.0735(6) 0.3111(2) 0.40511(18) 0.0621(8) Uani 1 1 d . . . H10A H -0.0441 0.3037 0.4464 0.075 Uiso 1 1 calc R . . C11 C 0.2665(6) 0.3619(2) 0.4255(2) 0.0703(9) Uani 1 1 d . . . H11A H 0.2811 0.3879 0.4806 0.084 Uiso 1 1 calc R . . C12 C 0.4404(6) 0.3743(2) 0.3637(2) 0.0690(8) Uani 1 1 d . . . H12A H 0.5717 0.4092 0.3770 0.083 Uiso 1 1 calc R . . C13 C 0.4178(5) 0.33453(18) 0.28221(18) 0.0548(6) Uani 1 1 d . . . H13A H 0.5341 0.3434 0.2406 0.066 Uiso 1 1 calc R . . C14 C 0.2286(4) 0.07889(16) 0.25575(14) 0.0406(5) Uani 1 1 d . . . C15 C 0.0211(5) 0.03177(15) 0.26246(15) 0.0465(5) Uani 1 1 d . . . H15A H -0.0794 0.0287 0.2148 0.056 Uiso 1 1 calc R . . C16 C -0.0381(5) -0.01104(17) 0.33984(16) 0.0523(6) Uani 1 1 d . . . H16A H -0.1792 -0.0424 0.3441 0.063 Uiso 1 1 calc R . . C17 C 0.1091(5) -0.00781(18) 0.41054(17) 0.0551(7) Uani 1 1 d . . . H17A H 0.0666 -0.0359 0.4626 0.066 Uiso 1 1 calc R . . C18 C 0.3187(5) 0.03689(19) 0.40412(17) 0.0561(7) Uani 1 1 d . . . H18A H 0.4202 0.0380 0.4515 0.067 Uiso 1 1 calc R . . C19 C 0.3801(5) 0.08066(18) 0.32678(16) 0.0509(6) Uani 1 1 d . . . H19A H 0.5224 0.1111 0.3226 0.061 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 C1 0.0426(13) 0.0541(13) 0.0342(11) 0.0068(11) 0.0029(10) -0.0014(11) C2 0.0446(13) 0.0582(15) 0.0316(11) -0.0001(10) 0.0030(10) 0.0080(11) O3 0.0763(13) 0.0573(11) 0.0329(8) -0.0063(8) -0.0027(8) 0.0193(10) S4 0.0507(3) 0.0543(3) 0.0303(2) 0.0001(2) -0.0001(3) 0.0021(3) N5 0.0462(11) 0.0551(10) 0.0363(9) -0.0033(9) 0.0002(9) 0.0099(11) O6 0.0635(11) 0.0749(11) 0.0295(8) 0.0058(8) 0.0027(8) 0.0030(9) O7 0.0593(11) 0.0699(12) 0.0658(12) -0.0099(11) -0.0012(10) -0.0138(10) C8 0.0453(13) 0.0446(12) 0.0367(11) 0.0026(10) 0.0003(9) 0.0017(10) C9 0.0514(16) 0.0545(13) 0.0420(12) -0.0042(11) 0.0037(10) -0.0020(12) C10 0.070(2) 0.0724(18) 0.0436(13) -0.0068(14) 0.0096(13) 0.0067(15) C11 0.077(2) 0.081(2) 0.0530(17) -0.0219(15) -0.0121(15) 0.0123(18) C12 0.0634(19) 0.0695(17) 0.0741(19) -0.0156(16) -0.0186(15) 0.0004(15) C13 0.0458(13) 0.0592(15) 0.0593(16) -0.0008(14) -0.0023(12) -0.0020(12) C14 0.0444(13) 0.0455(12) 0.0318(11) -0.0008(10) -0.0004(9) 0.0088(10) C15 0.0492(13) 0.0519(12) 0.0385(11) -0.0007(10) -0.0075(11) 0.0035(12) C16 0.0505(15) 0.0528(13) 0.0537(15) 0.0059(11) 0.0019(12) -0.0044(12) C17 0.0681(18) 0.0570(16) 0.0400(13) 0.0099(12) 0.0019(13) 0.0041(14) C18 0.0597(17) 0.0673(16) 0.0414(13) 0.0101(13) -0.0148(13) -0.0022(14) C19 0.0470(14) 0.0571(14) 0.0485(13) 0.0070(13) -0.0111(11) 0.0001(12) _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 C1 N5 1.478(3) . ? C1 C8 1.510(3) . ? C1 C2 1.547(4) . ? C1 H1A 0.9800 . ? C2 O3 1.466(3) . ? C2 C14 1.505(3) . ? C2 H2A 0.9800 . ? O3 S4 1.5687(19) . ? S4 O7 1.4083(19) . ? S4 O6 1.4270(17) . ? S4 N5 1.6271(19) . ? N5 H5A 0.8600 . ? C8 C9 1.387(3) . ? C8 C13 1.388(3) . ? C9 C10 1.385(4) . ? C9 H9A 0.9300 . ? C10 C11 1.366(4) . ? C10 H10A 0.9300 . ? C11 C12 1.386(4) . ? C11 H11A 0.9300 . ? C12 C13 1.383(4) . ? C12 H12A 0.9300 . ? C13 H13A 0.9300 . ? C14 C15 1.376(4) . ? C14 C19 1.391(3) . ? C15 C16 1.382(3) . ? C15 H15A 0.9300 . ? C16 C17 1.373(4) . ? C16 H16A 0.9300 . ? C17 C18 1.369(4) . ? C17 H17A 0.9300 . ? C18 C19 1.391(4) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? 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 N5 C1 C8 113.95(19) . . ? N5 C1 C2 101.8(2) . . ? C8 C1 C2 114.57(19) . . ? N5 C1 H1A 108.7 . . ? C8 C1 H1A 108.7 . . ? C2 C1 H1A 108.7 . . ? O3 C2 C14 109.46(18) . . ? O3 C2 C1 104.69(18) . . ? C14 C2 C1 116.08(19) . . ? O3 C2 H2A 108.8 . . ? C14 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? C2 O3 S4 113.30(14) . . ? O7 S4 O6 116.90(12) . . ? O7 S4 O3 109.09(12) . . ? O6 S4 O3 108.36(11) . . ? O7 S4 N5 111.58(12) . . ? O6 S4 N5 112.99(10) . . ? O3 S4 N5 95.71(9) . . ? C1 N5 S4 107.08(16) . . ? C1 N5 H5A 126.5 . . ? S4 N5 H5A 126.5 . . ? C9 C8 C13 118.7(2) . . ? C9 C8 C1 122.6(2) . . ? C13 C8 C1 118.6(2) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9A 120.0 . . ? C8 C9 H9A 120.0 . . ? C11 C10 C9 121.0(3) . . ? C11 C10 H10A 119.5 . . ? C9 C10 H10A 119.5 . . ? C10 C11 C12 119.7(3) . . ? C10 C11 H11A 120.2 . . ? C12 C11 H11A 120.2 . . ? C13 C12 C11 119.7(3) . . ? C13 C12 H12A 120.2 . . ? C11 C12 H12A 120.2 . . ? C12 C13 C8 120.9(3) . . ? C12 C13 H13A 119.5 . . ? C8 C13 H13A 119.5 . . ? C15 C14 C19 119.2(2) . . ? C15 C14 C2 122.8(2) . . ? C19 C14 C2 117.9(2) . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H16A 119.7 . . ? C15 C16 H16A 119.7 . . ? C18 C17 C16 119.8(2) . . ? C18 C17 H17A 120.1 . . ? C16 C17 H17A 120.1 . . ? C17 C18 C19 120.1(3) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C14 120.0(3) . . ? C18 C19 H19A 120.0 . . ? C14 C19 H19A 120.0 . . ? 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 N5 C1 C2 O3 33.6(2) . . . . ? C8 C1 C2 O3 157.02(19) . . . . ? N5 C1 C2 C14 -87.2(2) . . . . ? C8 C1 C2 C14 36.2(3) . . . . ? C14 C2 O3 S4 112.96(18) . . . . ? C1 C2 O3 S4 -12.1(2) . . . . ? C2 O3 S4 O7 -127.41(16) . . . . ? C2 O3 S4 O6 104.32(16) . . . . ? C2 O3 S4 N5 -12.22(18) . . . . ? C8 C1 N5 S4 -166.91(16) . . . . ? C2 C1 N5 S4 -43.04(18) . . . . ? O7 S4 N5 C1 147.16(16) . . . . ? O6 S4 N5 C1 -78.70(17) . . . . ? O3 S4 N5 C1 34.03(16) . . . . ? N5 C1 C8 C9 37.0(3) . . . . ? C2 C1 C8 C9 -79.7(3) . . . . ? N5 C1 C8 C13 -146.3(2) . . . . ? C2 C1 C8 C13 97.0(3) . . . . ? C13 C8 C9 C10 -0.9(4) . . . . ? C1 C8 C9 C10 175.8(2) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 1.0(5) . . . . ? C10 C11 C12 C13 -0.6(5) . . . . ? C11 C12 C13 C8 -0.6(4) . . . . ? C9 C8 C13 C12 1.3(4) . . . . ? C1 C8 C13 C12 -175.5(2) . . . . ? O3 C2 C14 C15 -28.9(3) . . . . ? C1 C2 C14 C15 89.2(3) . . . . ? O3 C2 C14 C19 153.9(2) . . . . ? C1 C2 C14 C19 -87.9(3) . . . . ? C19 C14 C15 C16 1.8(3) . . . . ? C2 C14 C15 C16 -175.4(2) . . . . ? C14 C15 C16 C17 -0.5(4) . . . . ? C15 C16 C17 C18 -1.1(4) . . . . ? C16 C17 C18 C19 1.4(4) . . . . ? C17 C18 C19 C14 -0.1(4) . . . . ? C15 C14 C19 C18 -1.5(4) . . . . ? C2 C14 C19 C18 175.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N5 H5A O6 0.86 2.63 3.058(3) 111.9 2_455 _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.282 _refine_diff_density_min -0.287 _refine_diff_density_rms 0.042