# Electronic Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Green Chemistry' _journal_coden_cambridge 1048 #============================================================================= # 2. TITLE AND AUTHOR LIST _publ_section_title ; Multicomponent reactions in ionic liquids ; _publ_contact_author_email ladeira@chimie.ups-tlse.fr _publ_contact_author_name 'Sonia Ladeira' loop_ _publ_author_name 'Zhor El Asri' 'Yves Genisson' 'Frederic Guillen' 'Olivier Basl ' 'Nicolas Isambert' 'Maria del Mar Sanchez Duque' ; J.Rodriguez ; 'Thierry Constantieux' 'Jean-Christophe Plaquevent' data_crotonaldehyde _database_code_depnum_ccdc_archive 'CCDC 800251' #TrackingRef 'crotonaldehyde.cif' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C25 H22 N2 O2' _chemical_formula_sum 'C25 H22 N2 O2' _chemical_formula_weight 382.45 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration syn #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.4801(2) _cell_length_b 15.4593(8) _cell_length_c 19.1885(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1922.26(15) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 2943 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.21 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.985 _exptl_absorpt_correction_T_max 0.996 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180(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 Kappa APEX II' _diffrn_measurement_method \w-\f _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_unetI/netI 0.0416 _diffrn_reflns_number 10127 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.945 _diffrn_measured_fraction_theta_max 0.945 _reflns_number_total 3267 _reflns_number_gt 2802 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Giacovazzo et al, 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0380P)^2^+0.1130P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3267 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0731 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.245 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 O1 O 0.23712(18) 0.21618(8) 0.82963(6) 0.0217(3) Uani 1 1 d . . . O2 O 0.4450(2) 0.03272(9) 0.88443(7) 0.0278(3) Uani 1 1 d . . . N2 N 0.0901(2) 0.03077(10) 0.88109(8) 0.0190(4) Uani 1 1 d . . . N1 N -0.0671(2) 0.13805(10) 0.80530(7) 0.0179(4) Uani 1 1 d . . . C20 C 0.0504(3) -0.00088(12) 0.95011(9) 0.0188(4) Uani 1 1 d . . . C8 C -0.1047(3) 0.20430(13) 0.85632(9) 0.0193(4) Uani 1 1 d . . . C21 C -0.1381(3) 0.01625(13) 0.98185(10) 0.0228(5) Uani 1 1 d . . . H21 H -0.2376 0.0513 0.9589 0.027 Uiso 1 1 calc R . . C17 C 0.2673(3) 0.07436(12) 0.77877(9) 0.0218(4) Uani 1 1 d . . . H17 H 0.4086 0.0858 0.76 0.026 Uiso 1 1 calc R . . C12 C 0.0888(3) 0.31702(13) 0.91401(10) 0.0270(5) Uani 1 1 d . . . H12 H 0.2149 0.347 0.9216 0.032 Uiso 1 1 calc R . . C13 C 0.0758(3) 0.24957(13) 0.86793(9) 0.0200(4) Uani 1 1 d . . . C1 C 0.1390(3) 0.20575(13) 0.70964(9) 0.0210(4) Uani 1 1 d . . . C25 C 0.1961(3) -0.05053(12) 0.98550(10) 0.0232(4) Uani 1 1 d . . . H25 H 0.3257 -0.0626 0.9645 0.028 Uiso 1 1 calc R . . C14 C -0.0795(3) 0.04842(12) 0.83041(9) 0.0186(4) Uani 1 1 d . . . H14 H -0.2162 0.0382 0.8531 0.022 Uiso 1 1 calc R . . C18 C 0.2818(3) 0.04363(12) 0.85357(9) 0.0197(4) Uani 1 1 d . . . C24 C 0.1516(3) -0.08198(13) 1.05097(10) 0.0289(5) Uani 1 1 d . . . H24 H 0.2526 -0.1149 1.0751 0.035 Uiso 1 1 calc R . . C2 C -0.0358(3) 0.20795(14) 0.66789(10) 0.0287(5) Uani 1 1 d . . . H2 H -0.1575 0.1786 0.6822 0.034 Uiso 1 1 calc R . . C7 C 0.1416(3) 0.15768(12) 0.77873(10) 0.0191(4) Uani 1 1 d . . . C11 C -0.0909(3) 0.33971(14) 0.94920(11) 0.0311(5) Uani 1 1 d . . . H11 H -0.0887 0.3866 0.9812 0.037 Uiso 1 1 calc R . . C9 C -0.2827(3) 0.22562(12) 0.89130(9) 0.0246(5) Uani 1 1 d . . . H9 H -0.4074 0.1946 0.8839 0.03 Uiso 1 1 calc R . . C22 C -0.1808(3) -0.01787(13) 1.04718(10) 0.0276(5) Uani 1 1 d . . . H22 H -0.3113 -0.0074 1.068 0.033 Uiso 1 1 calc R . . C15 C -0.0536(3) -0.01210(13) 0.76872(10) 0.0240(4) Uani 1 1 d . . . H15A H -0.1641 -0.0014 0.7342 0.029 Uiso 1 1 calc R . . H15B H -0.0641 -0.0729 0.7845 0.029 Uiso 1 1 calc R . . C23 C -0.0365(3) -0.06667(14) 1.08219(10) 0.0292(5) Uani 1 1 d . . . H23 H -0.066 -0.0894 1.1271 0.035 Uiso 1 1 calc R . . C19 C 0.2886(3) -0.07792(14) 0.73007(11) 0.0361(5) Uani 1 1 d . . . H19A H 0.3113 -0.1013 0.7769 0.054 Uiso 1 1 calc R . . H19B H 0.4219 -0.0645 0.7085 0.054 Uiso 1 1 calc R . . H19C H 0.2157 -0.1208 0.7017 0.054 Uiso 1 1 calc R . . C16 C 0.1601(3) 0.00379(13) 0.73490(10) 0.0236(5) Uani 1 1 d . . . H16 H 0.1383 0.0267 0.6867 0.028 Uiso 1 1 calc R . . C10 C -0.2729(3) 0.29480(14) 0.93823(10) 0.0295(5) Uani 1 1 d . . . H10 H -0.3935 0.3113 0.9631 0.035 Uiso 1 1 calc R . . C4 C 0.1419(4) 0.29594(14) 0.58402(11) 0.0367(6) Uani 1 1 d . . . H4 H 0.1429 0.3263 0.541 0.044 Uiso 1 1 calc R . . C3 C -0.0332(4) 0.25287(15) 0.60527(10) 0.0359(5) Uani 1 1 d . . . H3 H -0.1532 0.2539 0.5768 0.043 Uiso 1 1 calc R . . C6 C 0.3139(3) 0.24956(14) 0.68826(10) 0.0284(5) Uani 1 1 d . . . H6 H 0.4338 0.2488 0.7167 0.034 Uiso 1 1 calc R . . C5 C 0.3162(4) 0.29474(14) 0.62564(11) 0.0356(5) Uani 1 1 d . . . H5 H 0.4371 0.3247 0.6115 0.043 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 O1 0.0160(7) 0.0225(8) 0.0265(7) -0.0056(6) 0.0001(5) -0.0025(6) O2 0.0145(8) 0.0376(9) 0.0315(8) 0.0055(7) -0.0026(6) -0.0015(7) N2 0.0125(9) 0.0224(9) 0.0220(8) 0.0013(7) -0.0009(6) 0.0001(7) N1 0.0155(9) 0.0182(8) 0.0201(8) 0.0004(7) 0.0010(6) -0.0007(7) C20 0.0204(10) 0.0146(10) 0.0214(9) -0.0022(8) -0.0024(8) -0.0025(9) C8 0.0217(12) 0.0173(10) 0.0190(9) 0.0023(8) -0.0033(8) 0.0021(9) C21 0.0204(11) 0.0227(11) 0.0254(10) 0.0004(9) -0.0012(8) 0.0029(9) C17 0.0175(11) 0.0237(11) 0.0242(10) -0.0008(8) 0.0035(8) 0.0000(8) C12 0.0252(12) 0.0240(12) 0.0317(11) -0.0037(9) -0.0033(9) -0.0017(9) C13 0.0176(11) 0.0212(11) 0.0211(10) 0.0015(8) -0.0005(8) 0.0039(9) C1 0.0237(11) 0.0159(10) 0.0234(10) -0.0020(8) 0.0028(8) 0.0020(8) C25 0.0216(11) 0.0191(11) 0.0289(10) -0.0007(9) -0.0010(8) 0.0012(9) C14 0.0137(10) 0.0208(10) 0.0214(9) 0.0024(8) -0.0028(8) -0.0015(9) C18 0.0171(12) 0.0159(10) 0.0262(9) -0.0020(8) 0.0004(8) -0.0004(9) C24 0.0325(12) 0.0251(12) 0.0291(11) 0.0049(9) -0.0088(9) 0.0032(9) C2 0.0278(12) 0.0317(12) 0.0268(10) 0.0037(10) 0.0018(9) 0.0028(10) C7 0.0151(10) 0.0205(11) 0.0215(10) -0.0055(8) -0.0005(8) -0.0023(8) C11 0.0371(14) 0.0278(12) 0.0284(11) -0.0061(10) -0.0016(10) 0.0050(10) C9 0.0208(11) 0.0242(12) 0.0288(10) 0.0031(9) 0.0009(8) 0.0038(9) C22 0.0281(12) 0.0281(12) 0.0264(10) 0.0010(9) 0.0073(9) -0.0001(10) C15 0.0237(11) 0.0207(11) 0.0275(10) -0.0019(9) -0.0045(8) -0.0016(9) C23 0.0389(13) 0.0265(12) 0.0223(10) 0.0047(9) 0.0008(9) -0.0016(10) C19 0.0376(13) 0.0288(13) 0.0418(13) -0.0069(10) 0.0054(10) 0.0000(11) C16 0.0255(11) 0.0207(11) 0.0247(10) -0.0030(9) 0.0019(8) -0.0011(9) C10 0.0279(12) 0.0314(12) 0.0294(11) 0.0017(10) 0.0066(9) 0.0100(10) C4 0.0544(16) 0.0269(12) 0.0287(11) 0.0091(10) 0.0125(11) 0.0152(12) C3 0.0391(14) 0.0377(13) 0.0308(11) 0.0057(11) -0.0016(10) 0.0140(12) C6 0.0289(12) 0.0261(11) 0.0302(11) -0.0013(10) 0.0043(9) -0.0022(10) C5 0.0418(14) 0.0245(12) 0.0407(13) 0.0037(10) 0.0156(11) -0.0019(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C13 1.378(2) . ? O1 C7 1.468(2) . ? O2 C18 1.223(2) . ? N2 C18 1.365(2) . ? N2 C20 1.435(2) . ? N2 C14 1.492(2) . ? N1 C8 1.438(2) . ? N1 C14 1.469(2) . ? N1 C7 1.477(2) . ? C20 C21 1.390(3) . ? C20 C25 1.394(3) . ? C8 C9 1.375(3) . ? C8 C13 1.381(3) . ? C21 C22 1.388(3) . ? C21 H21 0.95 . ? C17 C18 1.515(2) . ? C17 C7 1.524(3) . ? C17 C16 1.543(3) . ? C17 H17 1 . ? C12 C13 1.370(3) . ? C12 C11 1.391(3) . ? C12 H12 0.95 . ? C1 C6 1.382(3) . ? C1 C2 1.388(3) . ? C1 C7 1.520(3) . ? C25 C24 1.378(3) . ? C25 H25 0.95 . ? C14 C15 1.518(2) . ? C14 H14 1 . ? C24 C23 1.378(3) . ? C24 H24 0.95 . ? C2 C3 1.388(3) . ? C2 H2 0.95 . ? C11 C10 1.385(3) . ? C11 H11 0.95 . ? C9 C10 1.400(3) . ? C9 H9 0.95 . ? C22 C23 1.376(3) . ? C22 H22 0.95 . ? C15 C16 1.549(3) . ? C15 H15A 0.99 . ? C15 H15B 0.99 . ? C23 H23 0.95 . ? C19 C16 1.516(3) . ? C19 H19A 0.98 . ? C19 H19B 0.98 . ? C19 H19C 0.98 . ? C16 H16 1 . ? C10 H10 0.95 . ? C4 C3 1.377(3) . ? C4 C5 1.384(3) . ? C4 H4 0.95 . ? C3 H3 0.95 . ? C6 C5 1.390(3) . ? C6 H6 0.95 . ? C5 H5 0.95 . ? 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 C13 O1 C7 105.41(13) . . ? C18 N2 C20 124.76(15) . . ? C18 N2 C14 113.05(14) . . ? C20 N2 C14 122.11(14) . . ? C8 N1 C14 116.06(14) . . ? C8 N1 C7 104.11(14) . . ? C14 N1 C7 110.90(14) . . ? C21 C20 C25 119.13(17) . . ? C21 C20 N2 119.80(17) . . ? C25 C20 N2 121.05(17) . . ? C9 C8 C13 120.70(17) . . ? C9 C8 N1 130.20(17) . . ? C13 C8 N1 109.11(15) . . ? C22 C21 C20 119.88(18) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C18 C17 C7 107.38(15) . . ? C18 C17 C16 108.85(15) . . ? C7 C17 C16 110.90(15) . . ? C18 C17 H17 109.9 . . ? C7 C17 H17 109.9 . . ? C16 C17 H17 109.9 . . ? C13 C12 C11 116.99(18) . . ? C13 C12 H12 121.5 . . ? C11 C12 H12 121.5 . . ? C12 C13 O1 125.64(17) . . ? C12 C13 C8 122.81(17) . . ? O1 C13 C8 111.51(16) . . ? C6 C1 C2 119.05(17) . . ? C6 C1 C7 119.29(17) . . ? C2 C1 C7 121.64(16) . . ? C24 C25 C20 119.80(18) . . ? C24 C25 H25 120.1 . . ? C20 C25 H25 120.1 . . ? N1 C14 N2 110.25(14) . . ? N1 C14 C15 108.64(14) . . ? N2 C14 C15 108.31(15) . . ? N1 C14 H14 109.9 . . ? N2 C14 H14 109.9 . . ? C15 C14 H14 109.9 . . ? O2 C18 N2 125.42(16) . . ? O2 C18 C17 123.75(16) . . ? N2 C18 C17 110.83(15) . . ? C25 C24 C23 121.38(19) . . ? C25 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C1 C2 C3 120.15(19) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? O1 C7 N1 106.44(13) . . ? O1 C7 C1 106.49(14) . . ? N1 C7 C1 113.04(14) . . ? O1 C7 C17 107.16(14) . . ? N1 C7 C17 108.40(15) . . ? C1 C7 C17 114.80(15) . . ? C10 C11 C12 120.85(19) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C8 C9 C10 117.34(18) . . ? C8 C9 H9 121.3 . . ? C10 C9 H9 121.3 . . ? C23 C22 C21 120.93(19) . . ? C23 C22 H22 119.5 . . ? C21 C22 H22 119.5 . . ? C14 C15 C16 109.11(15) . . ? C14 C15 H15A 109.9 . . ? C16 C15 H15A 109.9 . . ? C14 C15 H15B 109.9 . . ? C16 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C22 C23 C24 118.85(19) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C19 C16 C17 112.05(16) . . ? C19 C16 C15 112.61(17) . . ? C17 C16 C15 106.62(15) . . ? C19 C16 H16 108.5 . . ? C17 C16 H16 108.5 . . ? C15 C16 H16 108.5 . . ? C11 C10 C9 121.31(18) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C3 C4 C5 119.67(19) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C4 C3 C2 120.5(2) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C1 C6 C5 120.8(2) . . ? C1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C4 C5 C6 119.8(2) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? #===END