# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr Martyn J Earle' _publ_contact_author_address ; The QUILL Centre The Queen's University of Belfast Stranmillis Road Belfast BT9 5AG UK ; _publ_contact_author_email M.EARLE@QUB.AC.UK _publ_section_title ; Metal bis{(trifluoromethyl)sulfonyl}amide complexes: Highly efficient Friedel-Crafts acylation catalysts. ; loop_ _publ_author_name 'Martyn J. Earle' 'Ullastiina Hakala' 'Barry J. McAuley' 'Mark Nieuwenhuyzen' 'Alwar Ramani' ; K.R.Seddon ; data_zntfmm _database_code_depnum_ccdc_archive 'CCDC 219662' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 F12 N2 O8 S4 Zn' _chemical_formula_weight 625.67 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' 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 11.556(6) _cell_length_b 5.160(2) _cell_length_c 14.189(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.753(10) _cell_angle_gamma 90.00 _cell_volume 831.1(7) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 2.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 2.154 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.588 _exptl_absorpt_correction_T_max 0.928 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 3810 _diffrn_reflns_av_R_equivalents 0.0904 _diffrn_reflns_av_sigmaI/netI 0.1287 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1439 _reflns_number_gt 779 _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^)+(0.1015P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1439 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1306 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1892 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _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 Zn1 Zn 0.5000 0.0000 0.5000 0.0181(5) Uani 1 2 d S . . F11 F 0.8771(6) -0.5313(14) 0.3924(5) 0.047(2) Uani 1 1 d . . . F12 F 0.9125(5) -0.2139(14) 0.4910(4) 0.0400(18) Uani 1 1 d . . . F13 F 0.8097(6) -0.5392(13) 0.5238(5) 0.0460(19) Uani 1 1 d . . . C1 C 0.8337(10) -0.391(2) 0.4547(8) 0.027(3) Uani 1 1 d . . . N1 N 0.6215(8) -0.4613(17) 0.3593(7) 0.030(2) Uani 1 1 d . . . S1 S 0.7011(2) -0.2210(5) 0.39403(18) 0.0216(7) Uani 1 1 d . . . O11 O 0.6625(6) -0.0818(12) 0.4729(5) 0.0211(17) Uani 1 1 d . . . O12 O 0.7340(7) -0.0717(14) 0.3190(5) 0.034(2) Uani 1 1 d . . . S2 S 0.4902(2) -0.5008(5) 0.35898(16) 0.0166(6) Uani 1 1 d . . . O21 O 0.4353(6) -0.3162(12) 0.4157(4) 0.0179(16) Uani 1 1 d . . . O22 O 0.4645(6) -0.7691(13) 0.3748(5) 0.0245(17) Uani 1 1 d . . . C2 C 0.4162(10) -0.445(2) 0.2347(8) 0.026(3) Uani 1 1 d . . . F21 F 0.4357(6) -0.2025(12) 0.2119(4) 0.0398(18) Uani 1 1 d . . . F22 F 0.4575(6) -0.6052(13) 0.1768(4) 0.0404(18) Uani 1 1 d . . . F23 F 0.3020(6) -0.4816(13) 0.2265(5) 0.0426(18) 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 Zn1 0.0245(10) 0.0178(9) 0.0143(9) -0.0010(8) 0.0102(7) 0.0006(8) F11 0.033(4) 0.068(5) 0.040(4) -0.018(4) 0.004(3) 0.025(4) F12 0.025(4) 0.057(5) 0.037(4) -0.010(4) 0.003(3) -0.008(3) F13 0.047(4) 0.060(5) 0.029(4) 0.020(4) 0.002(3) 0.001(4) C1 0.027(6) 0.032(6) 0.021(6) -0.019(6) 0.006(5) 0.000(5) N1 0.027(5) 0.033(6) 0.030(5) -0.015(5) 0.003(4) -0.003(4) S1 0.0238(15) 0.0273(15) 0.0149(14) -0.0011(12) 0.0067(11) 0.0010(12) O11 0.024(4) 0.021(4) 0.021(4) -0.011(3) 0.013(3) -0.004(3) O12 0.046(5) 0.033(5) 0.029(5) 0.010(4) 0.016(4) 0.004(4) S2 0.0234(14) 0.0166(13) 0.0107(13) -0.0009(12) 0.0062(10) 0.0014(12) O21 0.025(4) 0.020(4) 0.012(3) 0.002(3) 0.010(3) 0.003(3) O22 0.038(5) 0.022(4) 0.017(4) 0.001(3) 0.012(3) -0.002(3) C2 0.036(7) 0.024(7) 0.018(6) 0.004(5) 0.002(5) -0.002(5) F21 0.063(5) 0.033(4) 0.023(4) 0.013(3) 0.008(3) -0.004(3) F22 0.071(5) 0.039(4) 0.013(3) -0.007(3) 0.014(3) 0.003(4) F23 0.032(4) 0.047(4) 0.044(4) 0.004(4) -0.004(3) -0.002(3) _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 Zn1 O11 2.030(7) 3_656 ? Zn1 O11 2.030(7) . ? Zn1 O21 2.078(6) 3_656 ? Zn1 O21 2.078(6) . ? Zn1 O22 2.114(7) 3_646 ? Zn1 O22 2.114(7) 1_565 ? F11 C1 1.311(11) . ? F12 C1 1.324(12) . ? F13 C1 1.314(13) . ? C1 S1 1.835(11) . ? N1 S2 1.531(9) . ? N1 S1 1.567(9) . ? S1 O12 1.423(7) . ? S1 O11 1.467(7) . ? S2 O22 1.442(7) . ? S2 O21 1.465(7) . ? S2 C2 1.833(11) . ? O22 Zn1 2.114(7) 1_545 ? C2 F23 1.316(13) . ? C2 F22 1.317(12) . ? C2 F21 1.322(12) . ? 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 O11 Zn1 O11 180.000(1) 3_656 . ? O11 Zn1 O21 88.5(2) 3_656 3_656 ? O11 Zn1 O21 91.5(2) . 3_656 ? O11 Zn1 O21 91.5(2) 3_656 . ? O11 Zn1 O21 88.5(2) . . ? O21 Zn1 O21 180.000(1) 3_656 . ? O11 Zn1 O22 90.0(3) 3_656 3_646 ? O11 Zn1 O22 90.0(3) . 3_646 ? O21 Zn1 O22 88.1(3) 3_656 3_646 ? O21 Zn1 O22 91.9(3) . 3_646 ? O11 Zn1 O22 90.0(3) 3_656 1_565 ? O11 Zn1 O22 90.0(3) . 1_565 ? O21 Zn1 O22 91.9(3) 3_656 1_565 ? O21 Zn1 O22 88.1(3) . 1_565 ? O22 Zn1 O22 180.000(1) 3_646 1_565 ? F11 C1 F13 110.1(9) . . ? F11 C1 F12 108.8(9) . . ? F13 C1 F12 109.7(9) . . ? F11 C1 S1 109.8(7) . . ? F13 C1 S1 110.7(8) . . ? F12 C1 S1 107.8(8) . . ? S2 N1 S1 129.0(6) . . ? O12 S1 O11 117.9(4) . . ? O12 S1 N1 114.6(5) . . ? O11 S1 N1 112.5(5) . . ? O12 S1 C1 107.0(5) . . ? O11 S1 C1 102.9(4) . . ? N1 S1 C1 99.1(5) . . ? S1 O11 Zn1 132.0(4) . . ? O22 S2 O21 114.6(4) . . ? O22 S2 N1 111.1(5) . . ? O21 S2 N1 116.2(4) . . ? O22 S2 C2 103.2(4) . . ? O21 S2 C2 104.7(5) . . ? N1 S2 C2 105.5(5) . . ? S2 O21 Zn1 132.9(4) . . ? S2 O22 Zn1 131.2(4) . 1_545 ? F23 C2 F22 109.2(9) . . ? F23 C2 F21 109.1(9) . . ? F22 C2 F21 110.0(9) . . ? F23 C2 S2 110.1(8) . . ? F22 C2 S2 110.0(7) . . ? F21 C2 S2 108.3(7) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.053 _refine_diff_density_min -1.106 _refine_diff_density_rms 0.205