Supplementary Material (ESI) for Green Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 1048 loop_ _publ_author_name 'Shaowu Wang' 'Enhong Sheng' 'Lijun Zhang' 'Shuangliu Zhou' _publ_contact_author_name 'ProfD Shaowu Wang' _publ_contact_author_address ; Institute of Organic Chemistry Anhui Normal University School of Chemistry and Materials S Wuhu Anhui 241000 CHINA ; _publ_contact_author_email SWWANG@MAIL.AHNU.EDU.CN _publ_requested_journal 'Green Chemistry' _publ_section_title ; A solvent-free synthesis of alpa, alpha'-bis(substituted benzylidene)cycloalkanones catalyzed by lanthanide amides [(Me3Si)2N]3Ln(mu-Cl)Li(THF)3 under microwave irradiation ; data_1 _database_code_depnum_ccdc_archive 'CCDC 268269' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 Cl2 O' _chemical_formula_weight 343.23 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0665(4) _cell_length_b 16.6372(7) _cell_length_c 10.5634(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.793(2) _cell_angle_gamma 90.00 _cell_volume 1684.52(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2559 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 25.04 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.387 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2865 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens SMART CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% none _diffrn_reflns_number 5278 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.04 _reflns_number_total 2916 _reflns_number_gt 2258 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens SMART' _computing_cell_refinement 'Siemens SMART & SAINT' _computing_data_reduction 'Siemens SMART & SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0203P)^2^+1.5572P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2916 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0707 _refine_ls_wR_factor_ref 0.1420 _refine_ls_wR_factor_gt 0.1275 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.187 _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 O O 0.1692(3) 0.05279(17) -0.1072(2) 0.0771(8) Uani 1 1 d . . . Cl1 Cl 0.93475(11) 0.16246(8) 0.51672(11) 0.0943(4) Uani 1 1 d . . . Cl2 Cl -0.71519(12) 0.14792(8) -0.38553(15) 0.1104(5) Uani 1 1 d . . . C1 C 0.7774(4) 0.1453(2) 0.3951(3) 0.0660(10) Uani 1 1 d . . . C2 C 0.7565(4) 0.0753(2) 0.3228(4) 0.0681(10) Uani 1 1 d . . . H2A H 0.8273 0.0373 0.3374 0.082 Uiso 1 1 calc R . . C3 C 0.6299(4) 0.0619(2) 0.2286(4) 0.0638(9) Uani 1 1 d . . . H3A H 0.6171 0.0150 0.1782 0.077 Uiso 1 1 calc R . . C4 C 0.5204(4) 0.1165(2) 0.2065(3) 0.0555(8) Uani 1 1 d . . . C5 C 0.5460(4) 0.1880(2) 0.2785(4) 0.0656(10) Uani 1 1 d . . . H5A H 0.4762 0.2267 0.2633 0.079 Uiso 1 1 calc R . . C6 C 0.6731(4) 0.2022(2) 0.3718(4) 0.0748(11) Uani 1 1 d . . . H6A H 0.6886 0.2502 0.4191 0.090 Uiso 1 1 calc R . . C7 C 0.3879(4) 0.0973(2) 0.1070(3) 0.0578(9) Uani 1 1 d . . . H7A H 0.3956 0.0667 0.0359 0.069 Uiso 1 1 calc R . . C8 C 0.2576(4) 0.11649(19) 0.1014(3) 0.0542(8) Uani 1 1 d . . . C9 C 0.2170(4) 0.1612(2) 0.2088(3) 0.0664(10) Uani 1 1 d . . . H9A H 0.2042 0.2178 0.1859 0.080 Uiso 1 1 calc R . . H9B H 0.2910 0.1566 0.2926 0.080 Uiso 1 1 calc R . . C10 C 0.0831(4) 0.1270(2) 0.2236(3) 0.0719(11) Uani 1 1 d . . . H10A H 0.0956 0.0701 0.2444 0.086 Uiso 1 1 calc R . . H10B H 0.0617 0.1535 0.2968 0.086 Uiso 1 1 calc R . . C11 C -0.0369(4) 0.1380(2) 0.0984(3) 0.0666(10) Uani 1 1 d . . . H11A H -0.0609 0.1945 0.0878 0.080 Uiso 1 1 calc R . . H11B H -0.1173 0.1092 0.1073 0.080 Uiso 1 1 calc R . . C12 C -0.0057(4) 0.10849(18) -0.0256(3) 0.0541(8) Uani 1 1 d . . . C13 C 0.1424(4) 0.08920(19) -0.0171(3) 0.0554(8) Uani 1 1 d . . . C14 C -0.1000(4) 0.09800(19) -0.1443(3) 0.0569(9) Uani 1 1 d . . . H14A H -0.0622 0.0787 -0.2085 0.068 Uiso 1 1 calc R . . C15 C -0.2507(4) 0.11061(19) -0.1942(3) 0.0582(9) Uani 1 1 d . . . C16 C -0.3196(4) 0.0851(2) -0.3227(4) 0.0693(10) Uani 1 1 d . . . H16A H -0.2683 0.0595 -0.3707 0.083 Uiso 1 1 calc R . . C17 C -0.4611(5) 0.0960(2) -0.3825(4) 0.0792(11) Uani 1 1 d . . . H17A H -0.5037 0.0785 -0.4689 0.095 Uiso 1 1 calc R . . C18 C -0.5375(4) 0.1333(2) -0.3118(5) 0.0781(11) Uani 1 1 d . . . C19 C -0.4751(5) 0.1582(2) -0.1843(5) 0.0833(12) Uani 1 1 d . . . H19A H -0.5281 0.1823 -0.1364 0.100 Uiso 1 1 calc R . . C20 C -0.3335(4) 0.1477(2) -0.1263(4) 0.0721(10) Uani 1 1 d . . . H20A H -0.2920 0.1657 -0.0398 0.087 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 O 0.0771(17) 0.0930(19) 0.0640(15) -0.0318(15) 0.0259(13) 0.0020(15) Cl1 0.0747(7) 0.1377(11) 0.0702(6) -0.0151(7) 0.0218(5) -0.0218(7) Cl2 0.0716(7) 0.1098(10) 0.1391(11) 0.0298(8) 0.0164(7) 0.0038(7) C1 0.074(2) 0.076(3) 0.054(2) -0.0039(19) 0.0280(18) -0.010(2) C2 0.069(2) 0.068(2) 0.076(2) -0.002(2) 0.035(2) 0.0024(19) C3 0.075(2) 0.056(2) 0.066(2) -0.0148(18) 0.031(2) -0.0014(19) C4 0.072(2) 0.0495(19) 0.0496(18) -0.0036(15) 0.0250(17) -0.0046(17) C5 0.077(3) 0.052(2) 0.066(2) -0.0054(18) 0.019(2) 0.0022(18) C6 0.092(3) 0.061(2) 0.072(2) -0.018(2) 0.026(2) -0.009(2) C7 0.079(2) 0.050(2) 0.0489(19) -0.0052(15) 0.0257(18) -0.0009(17) C8 0.074(2) 0.0420(18) 0.0491(19) -0.0009(14) 0.0225(17) 0.0001(16) C9 0.078(2) 0.068(2) 0.053(2) -0.0191(18) 0.0209(18) 0.001(2) C10 0.092(3) 0.077(3) 0.055(2) -0.0071(19) 0.033(2) 0.005(2) C11 0.084(3) 0.060(2) 0.063(2) -0.0079(18) 0.034(2) 0.0017(19) C12 0.071(2) 0.0396(17) 0.058(2) 0.0015(15) 0.0292(18) 0.0002(16) C13 0.074(2) 0.0421(17) 0.0545(19) -0.0017(15) 0.0260(17) -0.0003(16) C14 0.073(2) 0.0423(18) 0.060(2) 0.0031(16) 0.0269(18) 0.0017(16) C15 0.074(2) 0.0425(18) 0.060(2) 0.0069(16) 0.0232(18) -0.0024(17) C16 0.078(3) 0.066(2) 0.062(2) 0.0077(19) 0.019(2) 0.005(2) C17 0.087(3) 0.074(3) 0.070(3) 0.008(2) 0.014(2) -0.002(2) C18 0.075(3) 0.063(2) 0.091(3) 0.019(2) 0.018(2) -0.005(2) C19 0.085(3) 0.071(3) 0.103(3) 0.007(2) 0.042(3) 0.007(2) C20 0.078(3) 0.067(2) 0.073(2) -0.002(2) 0.026(2) 0.005(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 O C13 1.225(4) . ? Cl1 C1 1.731(4) . ? Cl1 Cl2 3.3643(16) 1_756 ? Cl2 C18 1.736(4) . ? C1 C2 1.374(5) . ? C1 C6 1.379(5) . ? C2 C3 1.374(5) . ? C3 C4 1.392(5) . ? C4 C5 1.393(4) . ? C4 C7 1.459(5) . ? C5 C6 1.375(5) . ? C7 C8 1.334(5) . ? C8 C13 1.494(5) . ? C8 C9 1.514(4) . ? C9 C10 1.515(5) . ? C10 C11 1.505(5) . ? C11 C12 1.519(4) . ? C12 C14 1.333(4) . ? C12 C13 1.500(5) . ? C14 C15 1.461(5) . ? C15 C16 1.389(5) . ? C15 C20 1.399(5) . ? C16 C17 1.382(5) . ? C17 C18 1.372(6) . ? C18 C19 1.366(6) . ? C19 C20 1.380(5) . ? 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 C1 Cl1 Cl2 148.30(14) . 1_756 ? C2 C1 C6 120.2(4) . . ? C2 C1 Cl1 120.2(3) . . ? C6 C1 Cl1 119.6(3) . . ? C1 C2 C3 119.4(4) . . ? C2 C3 C4 121.8(3) . . ? C3 C4 C5 117.5(3) . . ? C3 C4 C7 118.7(3) . . ? C5 C4 C7 123.8(3) . . ? C6 C5 C4 120.9(4) . . ? C5 C6 C1 120.1(3) . . ? C8 C7 C4 130.5(3) . . ? C7 C8 C13 117.7(3) . . ? C7 C8 C9 124.9(3) . . ? C13 C8 C9 117.3(3) . . ? C8 C9 C10 110.2(3) . . ? C11 C10 C9 111.3(3) . . ? C10 C11 C12 113.4(3) . . ? C14 C12 C13 116.0(3) . . ? C14 C12 C11 125.3(3) . . ? C13 C12 C11 118.7(3) . . ? O C13 C8 120.1(3) . . ? O C13 C12 120.6(3) . . ? C8 C13 C12 119.2(3) . . ? C12 C14 C15 133.1(3) . . ? C16 C15 C20 116.0(4) . . ? C16 C15 C14 117.5(3) . . ? C20 C15 C14 126.5(3) . . ? C17 C16 C15 122.9(4) . . ? C18 C17 C16 118.8(4) . . ? C19 C18 C17 120.6(4) . . ? C19 C18 Cl2 120.0(4) . . ? C17 C18 Cl2 119.4(4) . . ? C18 C19 C20 120.1(4) . . ? C19 C20 C15 121.7(4) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.197 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.040