# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Yu, Feng' 'Sun, Xiaomin' 'Jin, Zhichao' 'Wen, Shigang' 'Liang, Xinmiao' 'Ye, Jinxing' _publ_contact_author_name 'Liang, Xinmiao' _publ_contact_author_email liangxm@ecust.edu.cn _publ_section_title ; Enantioselective Michael Addition of Ketones to Maleimides Catalyzed by Bifunctional Monosulfonyl DPEN Salt ; # Attachment '- cd201160.cif' data_cd201160 _database_code_depnum_ccdc_archive 'CCDC 772273' #TrackingRef '- cd201160.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H12 Br N O3' _chemical_formula_weight 310.15 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' Br Br -0.2901 2.4595 '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, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.3371(16) _cell_length_b 11.773(3) _cell_length_c 17.660(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1317.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1966 _cell_measurement_theta_min 5.767 _cell_measurement_theta_max 45.103 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.358 _exptl_crystal_size_mid 0.301 _exptl_crystal_size_min 0.237 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.563 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 3.119 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.33881 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 7214 _diffrn_reflns_av_R_equivalents 0.0637 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2570 _reflns_number_gt 1730 _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^)+(0.0597P)^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 SHELXL _refine_ls_extinction_coef 0.0041(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.048(14) _chemical_absolute_configuration ad _refine_ls_number_reflns 2570 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.003 _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 Br1 Br 1.08759(13) -0.23823(5) 1.10632(3) 0.1201(4) Uani 1 1 d . . . N1 N 0.6625(5) 0.1275(3) 0.92215(17) 0.0479(8) Uani 1 1 d . . . O1 O 0.8285(6) 0.2843(3) 0.96980(19) 0.0789(10) Uani 1 1 d . . . O2 O 0.4623(6) 0.0082(3) 0.8507(2) 0.0913(12) Uani 1 1 d . . . O3 O 0.9090(6) 0.2381(3) 0.7867(2) 0.1049(14) Uani 1 1 d . . . C1 C 0.7037(7) 0.2433(4) 0.9276(2) 0.0522(10) Uani 1 1 d . . . C2 C 0.5187(7) 0.1033(4) 0.8659(3) 0.0585(12) Uani 1 1 d . . . C3 C 0.4488(7) 0.2112(4) 0.8301(3) 0.0666(12) Uani 1 1 d . . . H3A H 0.2974 0.2207 0.8353 0.080 Uiso 1 1 calc R . . H3B H 0.4846 0.2121 0.7767 0.080 Uiso 1 1 calc R . . C4 C 0.5657(7) 0.3045(4) 0.8722(2) 0.0529(10) Uani 1 1 d . . . H4 H 0.4610 0.3473 0.9014 0.063 Uiso 1 1 calc R . . C5 C 0.6884(7) 0.3897(4) 0.8244(3) 0.0627(12) Uani 1 1 d . . . H5A H 0.5940 0.4226 0.7871 0.075 Uiso 1 1 calc R . . H5B H 0.7378 0.4507 0.8568 0.075 Uiso 1 1 calc R . . C6 C 0.8742(9) 0.3384(6) 0.7842(3) 0.0781(15) Uani 1 1 d . . . C7 C 1.0105(11) 0.4206(6) 0.7424(4) 0.125(3) Uani 1 1 d . . . H7A H 1.1050 0.4570 0.7773 0.188 Uiso 1 1 calc R . . H7B H 0.9236 0.4768 0.7184 0.188 Uiso 1 1 calc R . . H7C H 1.0907 0.3808 0.7047 0.188 Uiso 1 1 calc R . . C8 C 0.7654(7) 0.0436(3) 0.9666(2) 0.0443(10) Uani 1 1 d . . . C9 C 0.9651(7) 0.0115(4) 0.9504(2) 0.0541(11) Uani 1 1 d . . . H9 H 1.0363 0.0463 0.9106 0.065 Uiso 1 1 calc R . . C10 C 1.0654(9) -0.0724(4) 0.9918(2) 0.0638(12) Uani 1 1 d . . . H10 H 1.2018 -0.0954 0.9800 0.077 Uiso 1 1 calc R . . C11 C 0.9577(9) -0.1198(4) 1.0503(2) 0.0631(13) Uani 1 1 d . . . C12 C 0.7572(9) -0.0897(4) 1.0686(3) 0.0690(13) Uani 1 1 d . . . H12 H 0.6870 -0.1245 1.1085 0.083 Uiso 1 1 calc R . . C13 C 0.6604(7) -0.0061(4) 1.0263(2) 0.0594(12) Uani 1 1 d . . . H13 H 0.5239 0.0169 1.0382 0.071 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 Br1 0.1991(9) 0.0953(5) 0.0659(4) 0.0154(3) -0.0062(4) 0.0815(5) N1 0.056(2) 0.0486(18) 0.0390(17) 0.0038(15) -0.0067(16) -0.0013(17) O1 0.102(3) 0.0560(19) 0.079(2) 0.0140(18) -0.036(2) -0.0201(19) O2 0.112(3) 0.069(2) 0.093(2) -0.005(2) -0.049(2) -0.010(2) O3 0.104(3) 0.090(3) 0.121(3) 0.017(3) 0.038(2) 0.051(3) C1 0.060(3) 0.050(3) 0.046(2) 0.004(2) -0.007(2) -0.001(2) C2 0.062(3) 0.060(3) 0.053(3) -0.002(2) -0.014(2) 0.001(2) C3 0.058(3) 0.075(3) 0.067(3) 0.014(3) -0.020(2) 0.004(2) C4 0.057(3) 0.055(2) 0.047(2) 0.0026(19) 0.004(2) 0.010(2) C5 0.069(3) 0.062(3) 0.057(3) 0.015(2) -0.003(2) 0.019(2) C6 0.071(4) 0.102(4) 0.061(3) 0.023(3) 0.000(3) 0.015(3) C7 0.107(5) 0.156(6) 0.112(5) 0.069(5) 0.047(4) 0.018(5) C8 0.048(3) 0.048(2) 0.037(2) -0.0047(18) -0.0074(19) -0.0003(19) C9 0.057(3) 0.059(3) 0.046(2) 0.005(2) -0.004(2) -0.005(2) C10 0.072(3) 0.063(3) 0.056(3) -0.007(2) -0.008(3) 0.018(3) C11 0.099(4) 0.051(3) 0.040(2) -0.002(2) -0.011(2) 0.026(3) C12 0.093(4) 0.067(3) 0.047(2) 0.015(2) 0.008(3) 0.008(3) C13 0.068(3) 0.059(3) 0.052(2) 0.008(2) 0.004(2) 0.002(2) _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 Br1 C11 1.897(4) . ? N1 C2 1.378(5) . ? N1 C1 1.392(5) . ? N1 C8 1.420(5) . ? O1 C1 1.189(5) . ? O2 C2 1.205(5) . ? O3 C6 1.202(6) . ? C1 C4 1.498(6) . ? C2 C3 1.487(6) . ? C3 C4 1.519(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.524(6) . ? C4 H4 0.9800 . ? C5 C6 1.502(7) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.492(8) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.352(6) . ? C8 C13 1.377(6) . ? C9 C10 1.383(6) . ? C9 H9 0.9300 . ? C10 C11 1.359(6) . ? C10 H10 0.9300 . ? C11 C12 1.357(7) . ? C12 C13 1.379(6) . ? C12 H12 0.9300 . ? C13 H13 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 C2 N1 C1 112.1(3) . . ? C2 N1 C8 123.9(3) . . ? C1 N1 C8 123.9(3) . . ? O1 C1 N1 124.5(4) . . ? O1 C1 C4 127.0(4) . . ? N1 C1 C4 108.5(3) . . ? O2 C2 N1 123.3(4) . . ? O2 C2 C3 127.6(4) . . ? N1 C2 C3 109.1(4) . . ? C2 C3 C4 105.4(3) . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3B 110.7 . . ? C4 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? C1 C4 C3 104.8(3) . . ? C1 C4 C5 112.4(4) . . ? C3 C4 C5 117.0(4) . . ? C1 C4 H4 107.4 . . ? C3 C4 H4 107.4 . . ? C5 C4 H4 107.4 . . ? C6 C5 C4 113.4(4) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? O3 C6 C7 123.3(6) . . ? O3 C6 C5 121.4(5) . . ? C7 C6 C5 115.2(5) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 119.7(4) . . ? C9 C8 N1 120.5(4) . . ? C13 C8 N1 119.8(4) . . ? C8 C9 C10 121.2(4) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C11 C10 C9 117.7(5) . . ? C11 C10 H10 121.2 . . ? C9 C10 H10 121.2 . . ? C12 C11 C10 122.9(4) . . ? C12 C11 Br1 118.3(4) . . ? C10 C11 Br1 118.7(4) . . ? C11 C12 C13 118.4(4) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C8 C13 C12 120.1(4) . . ? C8 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? 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 C2 N1 C1 O1 -176.9(4) . . . . ? C8 N1 C1 O1 0.0(6) . . . . ? C2 N1 C1 C4 3.1(5) . . . . ? C8 N1 C1 C4 180.0(3) . . . . ? C1 N1 C2 O2 179.0(5) . . . . ? C8 N1 C2 O2 2.1(7) . . . . ? C1 N1 C2 C3 -1.5(5) . . . . ? C8 N1 C2 C3 -178.4(4) . . . . ? O2 C2 C3 C4 178.8(5) . . . . ? N1 C2 C3 C4 -0.7(5) . . . . ? O1 C1 C4 C3 176.6(4) . . . . ? N1 C1 C4 C3 -3.4(5) . . . . ? O1 C1 C4 C5 48.5(6) . . . . ? N1 C1 C4 C5 -131.5(4) . . . . ? C2 C3 C4 C1 2.4(5) . . . . ? C2 C3 C4 C5 127.7(4) . . . . ? C1 C4 C5 C6 54.4(5) . . . . ? C3 C4 C5 C6 -67.0(5) . . . . ? C4 C5 C6 O3 4.8(7) . . . . ? C4 C5 C6 C7 -174.6(5) . . . . ? C2 N1 C8 C9 100.2(5) . . . . ? C1 N1 C8 C9 -76.3(5) . . . . ? C2 N1 C8 C13 -79.4(5) . . . . ? C1 N1 C8 C13 104.1(5) . . . . ? C13 C8 C9 C10 1.3(6) . . . . ? N1 C8 C9 C10 -178.2(4) . . . . ? C8 C9 C10 C11 -1.2(7) . . . . ? C9 C10 C11 C12 1.1(7) . . . . ? C9 C10 C11 Br1 178.1(3) . . . . ? C10 C11 C12 C13 -1.0(7) . . . . ? Br1 C11 C12 C13 -178.0(4) . . . . ? C9 C8 C13 C12 -1.2(7) . . . . ? N1 C8 C13 C12 178.3(4) . . . . ? C11 C12 C13 C8 1.0(7) . . . . ? 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 C3 H3B Br1 0.97 3.06 3.972(5) 157.3 2_654 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.477 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.057