Supplementary Material for PCCP This journal is © The Owner Societies 2010 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Paul Dyson' _publ_contact_author_email PAUL.DYSON@EPFL.CH _publ_section_title ; Nitrile functionalized pyrrolidinium ionic liquids as solvents for cross coupling reactions involving in situ generated nanoparticle catalyst reservoirs ; loop_ _publ_author_name 'Paul Dyson' 'Ilaria Biondi' 'Manish Chaubey' 'Cinzia Chiappe' 'Yugang Cui.' 'Zhaofu Fei.' ; C.G.Hartinger ; 'Yongdan Li.' 'Rosario Scopelliti' 'Xue Yang.' # Attachment 'pd344.cif' data_pd344 _database_code_depnum_ccdc_archive 'CCDC 751772' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H17 N2, I' _chemical_formula_sum 'C9 H17 I N2' _chemical_formula_weight 280.15 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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' '-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 13.0165(5) _cell_length_b 9.4458(5) _cell_length_c 18.5173(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2276.73(17) _cell_formula_units_Z 8 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 9505 _cell_measurement_theta_min 2.6588 _cell_measurement_theta_max 29.1591 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 2.770 _exptl_absorpt_correction_T_min 0.51222 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(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 'Oxford Diffraction KM4/Sapphire CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.2812 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13021 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0182 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1991 _reflns_number_gt 1621 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_cell_refinement ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _computing_data_reduction ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.5 (release 08-05-2007 CrysAlis171 .NET) (compiled May 8 2007,13:10:02) ; _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^)+(0.0329P)^2^+4.6206P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1991 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0302 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0641 _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_restrained_S_all 1.135 _refine_ls_shift/su_max 0.001 _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 I1 I 0.427592(18) 0.29976(3) 0.610388(13) 0.02619(11) Uani 1 1 d . . . N1 N 0.4471(2) 0.7530(3) 0.65293(17) 0.0217(7) Uani 1 1 d . . . N2 N 0.2948(3) 1.0146(4) 0.37571(19) 0.0419(9) Uani 1 1 d . . . C1 C 0.5506(3) 0.6999(5) 0.6305(2) 0.0306(9) Uani 1 1 d . . . H1A H 0.6002 0.7168 0.6694 0.046 Uiso 1 1 calc R . . H1B H 0.5728 0.7499 0.5868 0.046 Uiso 1 1 calc R . . H1C H 0.5466 0.5981 0.6205 0.046 Uiso 1 1 calc R . . C2 C 0.4049(3) 0.6721(4) 0.7172(2) 0.0265(9) Uani 1 1 d . . . H2A H 0.4598 0.6530 0.7529 0.032 Uiso 1 1 calc R . . H2B H 0.3744 0.5811 0.7017 0.032 Uiso 1 1 calc R . . C3 C 0.3226(3) 0.7702(4) 0.7491(2) 0.0301(9) Uani 1 1 d . . . H3A H 0.3253 0.7689 0.8025 0.036 Uiso 1 1 calc R . . H3B H 0.2532 0.7404 0.7334 0.036 Uiso 1 1 calc R . . C4 C 0.3483(3) 0.9197(4) 0.7198(2) 0.0299(9) Uani 1 1 d . . . H4A H 0.2950 0.9521 0.6854 0.036 Uiso 1 1 calc R . . H4B H 0.3534 0.9890 0.7597 0.036 Uiso 1 1 calc R . . C5 C 0.4515(3) 0.9020(4) 0.6820(2) 0.0265(8) Uani 1 1 d . . . H5A H 0.4595 0.9716 0.6425 0.032 Uiso 1 1 calc R . . H5B H 0.5091 0.9133 0.7165 0.032 Uiso 1 1 calc R . . C6 C 0.3718(3) 0.7371(4) 0.5906(2) 0.0215(8) Uani 1 1 d . . . H6A H 0.3011 0.7366 0.6102 0.026 Uiso 1 1 calc R . . H6B H 0.3836 0.6444 0.5671 0.026 Uiso 1 1 calc R . . C7 C 0.3798(3) 0.8529(4) 0.5338(2) 0.0255(8) Uani 1 1 d . . . H7A H 0.4515 0.8609 0.5163 0.031 Uiso 1 1 calc R . . H7B H 0.3590 0.9452 0.5545 0.031 Uiso 1 1 calc R . . C8 C 0.3079(3) 0.8121(4) 0.4712(2) 0.0279(9) Uani 1 1 d . . . H8A H 0.3337 0.7247 0.4479 0.033 Uiso 1 1 calc R . . H8B H 0.2385 0.7922 0.4905 0.033 Uiso 1 1 calc R . . C9 C 0.3012(3) 0.9249(5) 0.4173(2) 0.0291(9) Uani 1 1 d . . . 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 I1 0.02195(16) 0.02694(17) 0.02968(17) -0.00186(11) -0.00101(10) 0.00139(10) N1 0.0192(15) 0.0191(16) 0.0267(18) -0.0015(14) -0.0016(12) 0.0018(12) N2 0.047(2) 0.044(2) 0.035(2) 0.0028(18) -0.0101(17) 0.003(2) C1 0.0219(19) 0.030(2) 0.040(2) -0.0031(18) -0.0019(17) 0.0065(17) C2 0.031(2) 0.024(2) 0.025(2) 0.0048(16) -0.0058(16) -0.0006(17) C3 0.036(2) 0.032(2) 0.023(2) 0.0019(18) 0.0021(17) 0.0010(18) C4 0.037(2) 0.026(2) 0.026(2) -0.0034(17) 0.0028(17) 0.0024(19) C5 0.032(2) 0.0190(19) 0.029(2) -0.0023(17) -0.0041(16) -0.0001(17) C6 0.0200(18) 0.020(2) 0.024(2) -0.0028(15) -0.0017(15) -0.0024(16) C7 0.024(2) 0.030(2) 0.0226(19) 0.0010(16) -0.0003(16) -0.0006(17) C8 0.028(2) 0.032(2) 0.024(2) 0.0006(17) -0.0014(16) -0.0042(18) C9 0.026(2) 0.038(3) 0.024(2) -0.0065(19) -0.0049(16) -0.0005(19) _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 N1 C1 1.497(5) . ? N1 C5 1.509(5) . ? N1 C2 1.516(5) . ? N1 C6 1.521(5) . ? N2 C9 1.147(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.534(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.550(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.524(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.522(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.539(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.462(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 N1 C5 112.2(3) . . ? C1 N1 C2 112.0(3) . . ? C5 N1 C2 101.7(3) . . ? C1 N1 C6 109.6(3) . . ? C5 N1 C6 112.8(3) . . ? C2 N1 C6 108.2(3) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 104.5(3) . . ? N1 C2 H2A 110.8 . . ? C3 C2 H2A 110.8 . . ? N1 C2 H2B 110.8 . . ? C3 C2 H2B 110.8 . . ? H2A C2 H2B 108.9 . . ? 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 . . ? C5 C4 C3 104.5(3) . . ? C5 C4 H4A 110.9 . . ? C3 C4 H4A 110.9 . . ? C5 C4 H4B 110.9 . . ? C3 C4 H4B 110.9 . . ? H4A C4 H4B 108.9 . . ? N1 C5 C4 103.4(3) . . ? N1 C5 H5A 111.1 . . ? C4 C5 H5A 111.1 . . ? N1 C5 H5B 111.1 . . ? C4 C5 H5B 111.1 . . ? H5A C5 H5B 109.0 . . ? N1 C6 C7 114.2(3) . . ? N1 C6 H6A 108.7 . . ? C7 C6 H6A 108.7 . . ? N1 C6 H6B 108.7 . . ? C7 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? C6 C7 C8 107.4(3) . . ? C6 C7 H7A 110.2 . . ? C8 C7 H7A 110.2 . . ? C6 C7 H7B 110.2 . . ? C8 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? C9 C8 C7 111.6(3) . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? C7 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? N2 C9 C8 178.9(5) . . ? 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 C1 N1 C2 C3 160.1(3) . . . . ? C5 N1 C2 C3 40.1(4) . . . . ? C6 N1 C2 C3 -78.9(4) . . . . ? N1 C2 C3 C4 -19.8(4) . . . . ? C2 C3 C4 C5 -7.8(4) . . . . ? C1 N1 C5 C4 -165.1(3) . . . . ? C2 N1 C5 C4 -45.2(3) . . . . ? C6 N1 C5 C4 70.5(4) . . . . ? C3 C4 C5 N1 32.7(4) . . . . ? C1 N1 C6 C7 -79.9(4) . . . . ? C5 N1 C6 C7 45.9(4) . . . . ? C2 N1 C6 C7 157.7(3) . . . . ? N1 C6 C7 C8 173.7(3) . . . . ? C6 C7 C8 C9 173.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.664 _refine_diff_density_min -0.711 _refine_diff_density_rms 0.102