Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_master_file_afc7*.xtl _database_code_CSD 165558 _publ_requested_journal ? _journal_coden_Cambridge 182 _publ_contact_author ; Dr Min Shi Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 354 Fenglin Lu Shanghai 200032 ; _publ_requested_coeditor_name ? _publ_contact_author_phone ? _publ_contact_author_fax ? _publ_contact_author_email MSHI@PUB.SIOC.AC.CN loop_ _publ_author_name 'Min Shi' 'Yong-Mei Xu' _publ_section_title ; Lewis base effects in the Baylis-Hillman reaction of imines with 2-cyclohexen-1-one and 2-cyclopeten-1-one ; #------------------------------------------------------------------------------ _audit_creation_date 'Wed Jul 19 11:45:26 2001' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record ? #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan: PROCESS (MSC)' _computing_structure_solution SHELXS86 _computing_structure_refinement 'teXsan: LS (MSC)' _computing_publication_material 'teXsan: FINISH (MSC)' #------------------------------------------------------------------------------ _cell_length_a 7.935(3) _cell_length_b 10.593(3) _cell_length_c 22.562(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1896(1) _cell_formula_units_Z 4.00 _cell_measurement_temperature 20.0 _cell_measurement_reflns_used 20 _cell_measurement_theta_min 13.69 _cell_measurement_theta_max 20.68 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21 ' _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y,1/2+z' '1/2-x,1/2+y,1/2+z' '1/2+x,1/2-y, +z' #------------------------------------------------------------------------------ _exptl_crystal_description 'prismatic' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid ? _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_measured ? _exptl_crystal_F000 816.00 _exptl_absorpt_coefficient_mu_cm 1.976 #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 20.0 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoKalpha _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector ? _diffrn_measurement_device 'AFC7R' _diffrn_measurement_method 'omega/2-theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_decay_\% 1.65 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 2527 _diffrn_reflns_av_R_equivalents 0.00 _diffrn_reflns_av_sigmaI/Inet ? _diffrn_reflns_h_min 0 _diffrn_reflns_h_max 10 _diffrn_reflns_k_min 0 _diffrn_reflns_k_max 12 _diffrn_reflns_l_min 0 _diffrn_reflns_l_max 22 _diffrn_theta_min ? _diffrn_theta_max 27.5001 _diffrn_reflns_reduction_process ? _diffrn_orient_matrix_11 -0.00542 _diffrn_orient_matrix_12 0.00302 _diffrn_orient_matrix_13 -0.04426 _diffrn_orient_matrix_21 0.00291 _diffrn_orient_matrix_22 0.09433 _diffrn_orient_matrix_23 0.00137 _diffrn_orient_matrix_31 0.12588 _diffrn_orient_matrix_32 -0.00205 _diffrn_orient_matrix_33 -0.00194 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 84 0.003 0.002 'International Tables' H 0 92 0.000 0.000 'International Tables' O 0 16 0.011 0.006 'International Tables' N 0 4 0.006 0.003 'International Tables' S 0 4 0.125 0.123 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom S 0.2864(2) 0.0259(2) 0.0794 0.0478 Uij ? ? O1 0.3711(7) 0.1327(6) 0.1051(3) 0.0604 Uij ? ? O2 0.3798(7) -0.0848(5) 0.0667(3) 0.0621 Uij ? ? O3 -0.2280(10) -0.1023(8) 0.2445(4) 0.0963 Uij ? ? O4 0.416(1) 0.091(1) 0.3900(4) 0.1377 Uij ? ? N 0.1403(8) -0.0127(6) 0.1264(3) 0.0426 Uij ? ? C1 0.0668(10) 0.0825(7) 0.1675(5) 0.0477 Uij ? ? C2 -0.120(1) 0.0478(8) 0.1750(5) 0.0572 Uij ? ? C3 -0.134(1) -0.0766(10) 0.2046(5) 0.0623 Uij ? ? C4 -0.031(1) -0.1772(8) 0.1712(5) 0.0625 Uij ? ? C5 0.025(1) -0.1201(7) 0.1124(4) 0.0537 Uij ? ? C6 -0.128(1) -0.0730(8) 0.0803(5) 0.0671 Uij ? ? C7 -0.203(1) 0.0373(9) 0.1135(5) 0.0713 Uij ? ? C8 0.189(1) 0.0726(7) 0.0128(4) 0.0434 Uij ? ? C9 0.114(1) 0.1941(7) 0.0103(4) 0.0522 Uij ? ? C10 0.037(1) 0.2319(8) -0.0418(4) 0.0543 Uij ? ? C11 0.039(1) 0.1545(9) -0.0910(4) 0.0612 Uij ? ? C12 0.117(1) 0.0359(10) -0.0880(5) 0.0684 Uij ? ? C13 0.192(1) 0.0004(7) -0.0366(5) 0.0575 Uij ? ? C14 -0.049(1) 0.199(1) -0.1470(5) 0.0835 Uij ? ? C15 0.162(1) 0.0877(8) 0.2263(4) 0.0492 Uij ? ? C16 0.108(1) 0.175(1) 0.2695(6) 0.0878 Uij ? ? C17 0.194(2) 0.177(1) 0.3253(6) 0.0959 Uij ? ? C18 0.326(1) 0.097(1) 0.3336(6) 0.0870 Uij ? ? C19 0.388(2) 0.022(1) 0.2910(5) 0.0821 Uij ? ? C20 0.303(1) 0.0193(8) 0.2379(4) 0.0667 Uij ? ? C21 0.344(2) 0.128(2) 0.4379(7) 0.1511 Uij ? ? H1 0.0739 0.1638 0.1489 0.0892 Uij ? ? H2 -0.1756 0.1107 0.1979 0.0793 Uij ? ? H3 0.0644 -0.2007 0.1941 0.0892 Uij ? ? H4 -0.0993 -0.2494 0.1642 0.0892 Uij ? ? H5 0.1133 -0.1792 0.0975 0.0892 Uij ? ? H6 -0.0968 -0.0472 0.0415 0.0730 Uij ? ? H7 -0.2085 -0.1393 0.0777 0.0892 Uij ? ? H8 -0.1841 0.1130 0.0918 0.0892 Uij ? ? H9 -0.3211 0.0248 0.1180 0.0892 Uij ? ? H10 0.1163 0.2480 0.0439 0.0892 Uij ? ? H11 -0.0173 0.3119 -0.0435 0.1002 Uij ? ? H12 0.1170 -0.0184 -0.1215 0.0898 Uij ? ? H13 0.2500 -0.0785 -0.0353 0.0892 Uij ? ? H14 -0.1644 0.2138 -0.1389 0.0797 Uij ? ? H15 -0.0391 0.1354 -0.1767 0.1002 Uij ? ? H16 0.0025 0.2743 -0.1606 0.1002 Uij ? ? H17 0.0174 0.2322 0.2618 0.1030 Uij ? ? H18 0.1579 0.2310 0.3565 0.0892 Uij ? ? H19 0.4859 -0.0269 0.2974 0.1170 Uij ? ? H20 0.3462 -0.0340 0.2075 0.1002 Uij ? ? H21 0.4210 0.1189 0.4701 0.1809 Uij ? ? H22 0.2480 0.0767 0.4450 0.1809 Uij ? ? H23 0.3118 0.2132 0.4342 0.1818 Uij ? ? loop_ _atom_site_aniso_label _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 S 0.0394(8) 0.0479(10) 0.056(1) 0.001(1) 0.001(1) 0.007(1) O1 0.044(3) 0.080(4) 0.057(4) -0.023(3) -0.005(3) 0.012(3) O2 0.057(3) 0.059(3) 0.071(5) 0.021(3) 0.011(3) 0.010(3) O3 0.072(5) 0.125(6) 0.091(6) -0.007(5) 0.029(5) 0.026(5) O4 0.123(8) 0.21(1) 0.078(6) -0.035(8) -0.003(6) -0.019(7) N 0.043(3) 0.032(3) 0.053(5) -0.007(3) -0.006(3) 0.001(3) C1 0.043(5) 0.038(4) 0.062(6) 0.005(4) -0.003(5) 0.002(4) C2 0.040(5) 0.049(5) 0.083(8) 0.004(4) 0.000(5) 0.008(5) C3 0.041(5) 0.077(7) 0.069(7) -0.002(5) -0.003(5) 0.009(5) C4 0.063(6) 0.044(5) 0.081(7) -0.009(5) 0.002(6) 0.014(5) C5 0.048(5) 0.050(5) 0.064(6) -0.008(4) -0.008(5) 0.006(5) C6 0.061(5) 0.077(6) 0.064(6) -0.027(5) -0.004(7) 0.015(7) C7 0.052(5) 0.059(6) 0.103(8) 0.002(5) -0.021(6) 0.023(6) C8 0.040(5) 0.056(5) 0.034(5) 0.003(4) 0.004(4) 0.003(4) C9 0.052(6) 0.053(5) 0.052(6) 0.005(5) 0.004(5) -0.012(5) C10 0.063(5) 0.042(5) 0.058(6) 0.009(4) -0.003(6) 0.004(5) C11 0.073(7) 0.060(6) 0.050(6) -0.011(5) -0.009(6) 0.008(5) C12 0.086(7) 0.054(6) 0.065(7) -0.002(6) -0.026(6) -0.012(5) C13 0.073(7) 0.030(5) 0.070(7) 0.011(4) -0.004(6) -0.010(4) C14 0.092(9) 0.103(8) 0.056(6) 0.007(7) -0.017(6) -0.002(6) C15 0.044(5) 0.050(5) 0.054(6) -0.009(4) 0.007(4) -0.001(5) C16 0.062(7) 0.113(9) 0.089(9) 0.012(7) 0.018(7) -0.023(8) C17 0.080(9) 0.14(1) 0.071(8) -0.034(8) 0.036(7) -0.063(8) C18 0.066(8) 0.13(1) 0.060(8) -0.026(8) 0.008(6) 0.015(8) C19 0.113(9) 0.069(7) 0.064(7) -0.007(7) -0.016(7) 0.003(6) C20 0.094(8) 0.051(5) 0.054(6) -0.004(6) -0.025(6) 0.004(5) C21 0.12(1) 0.26(2) 0.072(10) -0.02(1) 0.010(9) -0.06(1) #------------------------------------------------------------------------------ _refine_special_details ? _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method 'Zachariasen_type_2_Gaussian_isotropic' _refine_ls_extinction_coef 3.39708 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1215 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_number_constraints ? _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0620 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0630 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.780 _refine_ls_shift/esd_max 0.0220 _refine_ls_shift/esd_mean ? _refine_diff_density_min 0.33140 _refine_diff_density_max -0.27360 #------------------------------------------------------------------------------ _geom_special_details ? 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 _geom_bond_publ_flag S O(1) 1.437(6) ? ? yes S O(2) 1.417(5) ? ? yes S N 1.624(7) ? ? yes S C(8) 1.761(8) ? ? yes O(3) C(3) 1.20(1) ? ? yes O(4) C(18) 1.46(1) ? ? yes O(4) C(21) 1.29(2) ? ? yes N C(1) 1.49(1) ? ? yes N C(5) 1.492(10) ? ? yes C(1) C(2) 1.54(1) ? ? yes C(1) C(15) 1.53(1) ? ? yes C(2) C(3) 1.48(1) ? ? yes C(2) C(7) 1.54(1) ? ? yes C(3) C(4) 1.54(1) ? ? yes C(4) C(5) 1.53(1) ? ? yes C(5) C(6) 1.50(1) ? ? yes C(6) C(7) 1.51(1) ? ? yes C(8) C(9) 1.42(1) ? ? yes C(8) C(13) 1.35(1) ? ? yes C(9) C(10) 1.38(1) ? ? yes C(10) C(11) 1.38(1) ? ? yes C(11) C(12) 1.40(1) ? ? yes C(11) C(14) 1.52(1) ? ? yes C(12) C(13) 1.36(1) ? ? yes C(15) C(16) 1.41(1) ? ? yes C(15) C(20) 1.36(1) ? ? yes C(16) C(17) 1.43(2) ? ? yes C(17) C(18) 1.36(2) ? ? yes C(18) C(19) 1.34(2) ? ? yes C(19) C(20) 1.37(1) ? ? yes #------------------------------------------------------------------------------ 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 _geom_bond_publ_flag O(1) S O(2) 119.2(4) ? ? ? yes O(1) S N 105.6(3) ? ? ? yes O(1) S C(8) 109.1(4) ? ? ? yes O(2) S N 107.3(3) ? ? ? yes O(2) S C(8) 106.8(4) ? ? ? yes N S C(8) 108.4(4) ? ? ? yes C(18) O(4) C(21) 119(1) ? ? ? yes S N C(1) 121.0(5) ? ? ? yes S N C(5) 119.3(6) ? ? ? yes C(1) N C(5) 114.2(6) ? ? ? yes N C(1) C(2) 106.5(7) ? ? ? yes N C(1) C(15) 111.8(6) ? ? ? yes C(2) C(1) C(15) 112.9(8) ? ? ? yes C(1) C(2) C(3) 109.6(7) ? ? ? yes C(1) C(2) C(7) 109.4(8) ? ? ? yes C(3) C(2) C(7) 108.0(8) ? ? ? yes O(3) C(3) C(2) 125.9(10) ? ? ? yes O(3) C(3) C(4) 122.6(9) ? ? ? yes C(2) C(3) C(4) 110.9(8) ? ? ? yes C(3) C(4) C(5) 107.9(7) ? ? ? yes N C(5) C(4) 107.3(7) ? ? ? yes N C(5) C(6) 110.1(7) ? ? ? yes C(4) C(5) C(6) 108.2(7) ? ? ? yes C(5) C(6) C(7) 109.9(8) ? ? ? yes C(2) C(7) C(6) 109.3(8) ? ? ? yes S C(8) C(9) 118.2(6) ? ? ? yes S C(8) C(13) 122.4(7) ? ? ? yes C(9) C(8) C(13) 119.2(8) ? ? ? yes C(8) C(9) C(10) 118.7(7) ? ? ? yes C(9) C(10) C(11) 120.6(8) ? ? ? yes C(10) C(11) C(12) 119.7(8) ? ? ? yes C(10) C(11) C(14) 119.0(9) ? ? ? yes C(12) C(11) C(14) 121.3(9) ? ? ? yes C(11) C(12) C(13) 119.0(9) ? ? ? yes C(8) C(13) C(12) 122.6(8) ? ? ? yes C(1) C(15) C(16) 118.1(9) ? ? ? yes C(1) C(15) C(20) 123.8(8) ? ? ? yes C(16) C(15) C(20) 118.0(10) ? ? ? yes C(15) C(16) C(17) 117(1) ? ? ? yes C(16) C(17) C(18) 118(1) ? ? ? yes O(4) C(18) C(17) 121(1) ? ? ? yes O(4) C(18) C(19) 114(1) ? ? ? yes C(17) C(18) C(19) 123(1) ? ? ? yes C(18) C(19) C(20) 117(1) ? ? ? yes C(15) C(20) C(19) 123(1) ? ? ? yes #------------------------------------------------------------------------------