Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Dr Robin Rogers' _publ_contact_author_address ; Center for Green Manufacturing and Department of Chemistry The University of Alabama PO BOX 870336 Tuscaloosa Alabama 35487 UNITED STATES OF AMERICA ; _publ_contact_author_phone '+1 205 3484323' _publ_contact_author_fax '+1 205 3489104' _publ_contact_author_email rdrogers@bama.ua.edu _publ_requested_journal 'Chemical Communications' _publ_requested_coeditor_name ? _publ_contact_letter ; ? ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Liquid Clathrate Formation in Ionic Liquid/Aromatic Mixtures ; loop_ _publ_author_name _publ_author_address 'Holbrey, John D.' ; Center for Green Manufacturing and Department of Chemistry University of Alabama Tuscaloosa AL 35487 USA ; 'Reichert, W. Matthew' ; Center for Green Manufacturing and Department of Chemistry University of Alabama Tuscaloosa AL 35487 USA ; 'Nieuwenhuyzen, Mark' ; Department of Chemistry Queen's University of Belfast Belfast BT9 5AG Northern Ireland, UK ; 'Sheppard, Oonagh' ; Department of Chemistry Queen's University of Belfast Belfast BT9 5AG Northern Ireland, UK ; 'Hardacre, Christopher' ; Department of Chemistry and QUILL Queen's University of Belfast Belfast BT9 5AG Northern Ireland, UK ; 'Rogers, Robin D.' ; Center for Green Manufacturing and Department of Chemistry University of Alabama Tuscaloosa AL 35487 USA ; data_john1 _database_code_CSD 200588 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; '1,3-dimethylimidazolium hexafluorophosphate' ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H9 F6 N2 P' _chemical_formula_weight 242.11 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 11.302(8) _cell_length_b 9.337(6) _cell_length_c 17.947(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1894(2) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 939 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.97 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 7832 _diffrn_reflns_av_R_equivalents 0.0331 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 23.37 _reflns_number_total 1372 _reflns_number_gt 1143 _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 '0.0461, 1.3707' _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 1372 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.068 _refine_ls_shift/su_mean 0.004 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 P1 P 0.92447(6) 0.16057(7) 0.36116(4) 0.0336(2) Uani 1 1 d . . . F6 F 1.03241(14) 0.21692(19) 0.41037(9) 0.0517(5) Uani 1 1 d . . . F4 F 0.81632(14) 0.10726(19) 0.31105(9) 0.0549(5) Uani 1 1 d . . . F5 F 0.98479(15) 0.22687(18) 0.28806(8) 0.0509(5) Uani 1 1 d . . . F3 F 0.86359(16) 0.0966(2) 0.43304(9) 0.0619(5) Uani 1 1 d . . . N1 N 1.18601(17) 0.4661(2) 0.35397(11) 0.0302(5) Uani 1 1 d . . . N2 N 1.04717(18) 0.5998(2) 0.39706(11) 0.0320(5) Uani 1 1 d . . . F2 F 0.99118(17) 0.01422(18) 0.34518(11) 0.0645(6) Uani 1 1 d . . . F1 F 0.85846(16) 0.30850(18) 0.37449(9) 0.0588(5) Uani 1 1 d . . . C2 C 1.0798(2) 0.5184(3) 0.34092(15) 0.0285(6) Uani 1 1 d . . . H2A H 1.038(2) 0.503(2) 0.3039(14) 0.020(6) Uiso 1 1 d . . . C5 C 1.2230(3) 0.5153(3) 0.42155(15) 0.0406(7) Uani 1 1 d . . . H5A H 1.299(2) 0.492(3) 0.4400(15) 0.040(8) Uiso 1 1 d . . . C4 C 1.1376(3) 0.5984(3) 0.44851(16) 0.0431(7) Uani 1 1 d . . . H4A H 1.130(3) 0.645(3) 0.4895(17) 0.052(9) Uiso 1 1 d . . . C7 C 1.2501(3) 0.3665(4) 0.30534(19) 0.0448(7) Uani 1 1 d . . . H7A H 1.221(3) 0.377(4) 0.257(2) 0.088(13) Uiso 1 1 d . . . H7B H 1.238(3) 0.271(4) 0.321(2) 0.076(11) Uiso 1 1 d . . . H7C H 1.330(4) 0.385(4) 0.310(2) 0.084(12) Uiso 1 1 d . . . C6 C 0.9344(3) 0.6771(4) 0.4030(2) 0.0496(8) Uani 1 1 d . . . H6A H 0.894(5) 0.662(5) 0.362(3) 0.13(2) Uiso 1 1 d . . . H6B H 0.944(4) 0.776(5) 0.409(2) 0.100(15) Uiso 1 1 d . . . H6C H 0.894(4) 0.647(5) 0.440(3) 0.121(18) Uiso 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 P1 0.0351(4) 0.0347(4) 0.0311(4) -0.0029(3) 0.0045(3) -0.0014(3) F6 0.0437(9) 0.0677(11) 0.0436(10) 0.0018(8) -0.0099(8) -0.0092(9) F4 0.0443(9) 0.0750(12) 0.0455(10) -0.0169(9) 0.0029(8) -0.0165(9) F5 0.0640(10) 0.0530(10) 0.0356(9) -0.0021(7) 0.0091(8) -0.0190(8) F3 0.0662(11) 0.0795(13) 0.0398(10) 0.0109(9) 0.0144(9) -0.0186(10) N1 0.0322(11) 0.0301(11) 0.0283(12) 0.0049(9) -0.0010(9) -0.0028(10) N2 0.0355(12) 0.0313(12) 0.0292(12) 0.0037(10) 0.0040(10) -0.0023(9) F2 0.0729(12) 0.0395(10) 0.0811(14) -0.0018(9) 0.0111(10) 0.0161(9) F1 0.0717(12) 0.0539(11) 0.0508(11) -0.0134(8) -0.0076(9) 0.0228(9) C2 0.0327(14) 0.0286(14) 0.0243(14) 0.0035(11) -0.0051(12) -0.0059(11) C5 0.0372(16) 0.0513(18) 0.0332(16) 0.0059(13) -0.0066(13) -0.0047(14) C4 0.0529(18) 0.0515(18) 0.0248(14) -0.0056(14) -0.0007(14) -0.0080(15) C7 0.0450(18) 0.0401(19) 0.049(2) -0.0011(15) 0.0082(15) 0.0101(15) C6 0.0446(17) 0.047(2) 0.057(2) 0.0053(17) 0.0143(17) 0.0102(15) _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 P1 F3 1.5795(18) . ? P1 F2 1.587(2) . ? P1 F1 1.5879(19) . ? P1 F6 1.5954(18) . ? P1 F4 1.5971(18) . ? P1 F5 1.6029(18) . ? N1 C2 1.316(3) . ? N1 C5 1.363(3) . ? N1 C7 1.467(4) . ? N2 C2 1.315(3) . ? N2 C4 1.377(4) . ? N2 C6 1.469(4) . ? C5 C4 1.330(4) . ? 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 F3 P1 F2 91.65(11) . . ? F3 P1 F1 90.08(11) . . ? F2 P1 F1 178.18(11) . . ? F3 P1 F6 90.33(10) . . ? F2 P1 F6 91.19(11) . . ? F1 P1 F6 89.38(10) . . ? F3 P1 F4 90.49(10) . . ? F2 P1 F4 89.62(11) . . ? F1 P1 F4 89.79(10) . . ? F6 P1 F4 178.83(11) . . ? F3 P1 F5 179.25(11) . . ? F2 P1 F5 89.00(10) . . ? F1 P1 F5 89.27(10) . . ? F6 P1 F5 90.03(10) . . ? F4 P1 F5 89.14(10) . . ? C2 N1 C5 108.2(2) . . ? C2 N1 C7 125.4(2) . . ? C5 N1 C7 126.3(2) . . ? C2 N2 C4 107.5(2) . . ? C2 N2 C6 125.7(3) . . ? C4 N2 C6 126.9(3) . . ? N2 C2 N1 109.5(2) . . ? C4 C5 N1 107.3(3) . . ? C5 C4 N2 107.5(3) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 23.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.361 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.048 #===END data_mimpf6m _database_code_CSD 200589 _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,3-dimethylimidazolium hexafluorophosphate' ; _chemical_name_common '1,3-dimethylimidazolium hexafluorophosphate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H9 F6 N2 P' _chemical_formula_weight 242.11 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' P P 0.1023 0.0942 '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' _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 11.254(2) _cell_length_b 9.3606(19) _cell_length_c 17.986(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1894.7(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.347 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.333 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _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 'Bruker SMART CCD' _diffrn_measurement_method 'Omega/phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10979 _diffrn_reflns_av_R_equivalents 0.0689 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 26.37 _reflns_number_total 1934 _reflns_number_gt 1377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_data_reduction 'Bruker SAINT version 6.02a (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0954P)^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 1934 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0708 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1528 _refine_ls_wR_factor_gt 0.1408 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C1 C 0.4352(2) 0.6787(3) 0.40356(18) 0.0497(8) Uani 1 1 d . . . H11 H 0.4264 0.7219 0.4445 0.075 Uiso 1 1 d R . . H12 H 0.3844 0.6408 0.3787 0.075 Uiso 1 1 d R . . H13 H 0.4436 0.7894 0.3759 0.075 Uiso 1 1 d R . . N1 N 0.54751(18) 0.6007(2) 0.39731(12) 0.0338(5) Uani 1 1 d . . . C2 C 0.6388(2) 0.5991(3) 0.44877(16) 0.0451(7) Uani 1 1 d . . . H2 H 0.6288 0.6511 0.4926 0.054 Uiso 1 1 d R . . C3 C 0.7237(2) 0.5153(3) 0.42143(15) 0.0426(7) Uani 1 1 d . . . H3 H 0.8003 0.4963 0.4391 0.051 Uiso 1 1 d R . . N2 N 0.68593(18) 0.4655(2) 0.35354(12) 0.0327(5) Uani 1 1 d . . . C4 C 0.5794(2) 0.5184(3) 0.34070(14) 0.0317(6) Uani 1 1 d . . . H4 H 0.5338 0.5067 0.3016 0.038 Uiso 1 1 d R . . C5 C 0.7491(2) 0.3648(3) 0.30505(17) 0.0454(7) Uani 1 1 d . . . H51 H 0.7312 0.3869 0.2578 0.068 Uiso 1 1 d R . . H52 H 0.7419 0.2630 0.3264 0.068 Uiso 1 1 d R . . H53 H 0.8279 0.3737 0.3116 0.068 Uiso 1 1 d R . . P1 P 0.42398(6) 0.16154(8) 0.36082(4) 0.0349(3) Uani 1 1 d . . . F11 F 0.49148(16) 0.01474(19) 0.34482(12) 0.0600(5) Uani 1 1 d . . . F12 F 0.35740(16) 0.3094(2) 0.37450(9) 0.0570(5) Uani 1 1 d . . . F13 F 0.36310(15) 0.09606(19) 0.43311(9) 0.0588(5) Uani 1 1 d . . . F14 F 0.31521(14) 0.10811(18) 0.31093(9) 0.0529(5) Uani 1 1 d . . . F15 F 0.53259(14) 0.21707(19) 0.41011(9) 0.0507(5) Uani 1 1 d . . . F16 F 0.48434(16) 0.22860(18) 0.28786(9) 0.0500(5) 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 C1 0.0474(17) 0.0465(19) 0.0552(19) 0.0000(14) 0.0114(14) 0.0096(15) N1 0.0396(12) 0.0277(12) 0.0340(12) 0.0036(9) 0.0042(9) -0.0021(10) C2 0.0539(17) 0.0492(19) 0.0322(14) -0.0037(13) -0.0040(13) -0.0074(14) C3 0.0405(14) 0.0528(19) 0.0344(15) 0.0039(12) -0.0060(12) -0.0039(14) N2 0.0364(12) 0.0291(12) 0.0325(11) 0.0032(9) -0.0003(9) -0.0018(9) C4 0.0384(14) 0.0277(14) 0.0291(12) 0.0034(10) -0.0041(11) -0.0061(11) C5 0.0492(17) 0.0403(17) 0.0466(17) 0.0010(13) 0.0071(14) 0.0092(13) P1 0.0399(4) 0.0321(5) 0.0328(4) -0.0016(3) 0.0040(3) -0.0008(3) F11 0.0706(12) 0.0357(11) 0.0737(13) -0.0006(9) 0.0090(9) 0.0149(8) F12 0.0716(12) 0.0495(11) 0.0499(11) -0.0131(8) -0.0066(9) 0.0215(10) F13 0.0663(11) 0.0676(13) 0.0424(10) 0.0098(9) 0.0120(9) -0.0145(10) F14 0.0473(10) 0.0664(13) 0.0451(10) -0.0125(9) 0.0030(8) -0.0144(8) F15 0.0483(10) 0.0589(11) 0.0449(10) 0.0035(8) -0.0092(8) -0.0096(9) F16 0.0658(11) 0.0461(10) 0.0381(9) -0.0014(7) 0.0058(8) -0.0165(8) _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 C1 N1 1.465(3) . ? N1 C4 1.326(3) . ? N1 C2 1.383(3) . ? C2 C3 1.330(4) . ? C3 N2 1.375(3) . ? N2 C4 1.318(3) . ? N2 C5 1.467(3) . ? P1 F13 1.5924(17) . ? P1 F12 1.5928(18) . ? P1 F11 1.5963(18) . ? P1 F15 1.5970(17) . ? P1 F14 1.5981(17) . ? P1 F16 1.6054(17) . ? 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 C4 N1 C2 107.9(2) . . ? C4 N1 C1 125.6(2) . . ? C2 N1 C1 126.5(2) . . ? C3 C2 N1 107.0(2) . . ? C2 C3 N2 107.9(2) . . ? C4 N2 C3 108.0(2) . . ? C4 N2 C5 125.3(2) . . ? C3 N2 C5 126.6(2) . . ? N2 C4 N1 109.3(2) . . ? F13 P1 F12 90.33(10) . . ? F13 P1 F11 91.18(11) . . ? F12 P1 F11 178.43(11) . . ? F13 P1 F15 90.08(9) . . ? F12 P1 F15 89.51(10) . . ? F11 P1 F15 90.92(11) . . ? F13 P1 F14 90.48(9) . . ? F12 P1 F14 89.90(10) . . ? F11 P1 F14 89.65(10) . . ? F15 P1 F14 179.20(11) . . ? F13 P1 F16 179.46(11) . . ? F12 P1 F16 89.18(10) . . ? F11 P1 F16 89.30(10) . . ? F15 P1 F16 90.15(9) . . ? F14 P1 F16 89.29(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.428 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.092 #===END data_dmbzpf6m _database_code_CSD 200590 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H12 F6 N2 P' _chemical_formula_weight 281.17 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.3616(8) _cell_length_b 11.7383(14) _cell_length_c 15.9061(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.002(2) _cell_angle_gamma 90.00 _cell_volume 1176.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Colourless _exptl_crystal_colour Block _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 572 _exptl_absorpt_coefficient_mu 0.292 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9440 _exptl_absorpt_correction_T_max 0.9714 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68670 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS Station 9.8 ' _diffrn_radiation_monochromator 'silicon 111' _diffrn_measurement_device_type 'Bruker SMART 1K CCD difractomer' _diffrn_measurement_method 'omega rotation with narrow frames' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8378 _diffrn_reflns_av_R_equivalents 0.0593 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 29.33 _reflns_number_total 3315 _reflns_number_gt 2992 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.28a (Bruker, 2001)' _computing_data_reduction 'Bruker SAINT version 6.28a (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0546P)^2^+0.2601P] 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 3315 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0506 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1158 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _refine_ls_shift/su_max 0.019 _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 C1 C -0.2311(4) 0.22436(19) -0.02290(12) 0.0626(5) Uani 1 1 d . . . H1A H -0.0858 0.2341 0.0059 0.094 Uiso 1 1 calc R . . H1B H -0.2804 0.2959 -0.0508 0.094 Uiso 1 1 calc R . . H1C H -0.2339 0.1639 -0.0655 0.094 Uiso 1 1 calc R . . N1 N -0.3702(2) 0.19338(10) 0.03918(7) 0.0350(3) Uani 1 1 d . . . C2 C -0.32931(19) 0.21074(10) 0.12215(8) 0.0289(2) Uani 1 1 d . . . H2A H -0.2030 0.2435 0.1511 0.035 Uiso 1 1 calc R . . N3 N -0.49189(18) 0.17521(9) 0.15805(7) 0.0324(2) Uani 1 1 d . . . C4 C -0.6423(2) 0.13312(13) 0.09568(12) 0.0491(4) Uani 1 1 d . . . H4A H -0.7754 0.1012 0.1035 0.059 Uiso 1 1 calc R . . C5 C -0.5670(3) 0.14521(14) 0.02185(11) 0.0503(4) Uani 1 1 d . . . H5A H -0.6373 0.1242 -0.0326 0.060 Uiso 1 1 calc R . . C6 C -0.5033(3) 0.17723(15) 0.24924(10) 0.0518(4) Uani 1 1 d . . . H6A H -0.3875 0.1313 0.2791 0.078 Uiso 1 1 calc R . . H6B H -0.6398 0.1458 0.2599 0.078 Uiso 1 1 calc R . . H6C H -0.4903 0.2559 0.2698 0.078 Uiso 1 1 calc R . . P1 P 0.06710(5) 0.42077(3) 0.293036(19) 0.02790(11) Uani 1 1 d . . . F11 F 0.04772(16) 0.54353(8) 0.24979(6) 0.0490(2) Uani 1 1 d . . . F12 F 0.08556(15) 0.29872(7) 0.33757(6) 0.0425(2) Uani 1 1 d . . . F13 F 0.05998(14) 0.47917(8) 0.38420(5) 0.0419(2) Uani 1 1 d . . . F14 F 0.07532(15) 0.36201(9) 0.20259(5) 0.0458(2) Uani 1 1 d . . . F15 F -0.18632(14) 0.41028(9) 0.27928(6) 0.0471(2) Uani 1 1 d . . . F16 F 0.32009(12) 0.43156(7) 0.30735(6) 0.0378(2) Uani 1 1 d . . . C1S C 0.5078(4) -0.02928(14) 0.41649(10) 0.0540(5) Uani 1 1 d . . . H1SA H 0.5131 -0.0494 0.3590 0.065 Uiso 1 1 calc R . . C2S C 0.3290(3) 0.02036(16) 0.43900(12) 0.0595(5) Uani 1 1 d . . . H2SA H 0.2103 0.0346 0.3971 0.071 Uiso 1 1 calc R . . C3S C 0.3207(3) 0.04998(16) 0.52298(13) 0.0570(4) Uani 1 1 d . . . H3SA H 0.1966 0.0845 0.5385 0.068 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 C1 0.0808(14) 0.0683(12) 0.0449(9) 0.0109(8) 0.0302(9) 0.0213(10) N1 0.0424(6) 0.0328(5) 0.0287(5) -0.0012(4) 0.0006(4) 0.0082(4) C2 0.0280(5) 0.0281(5) 0.0294(5) -0.0020(4) -0.0005(4) 0.0008(4) N3 0.0333(5) 0.0266(5) 0.0377(6) 0.0040(4) 0.0061(4) 0.0033(4) C4 0.0325(7) 0.0385(7) 0.0718(11) 0.0067(7) -0.0079(7) -0.0085(5) C5 0.0551(9) 0.0397(8) 0.0477(8) -0.0063(6) -0.0224(7) -0.0017(7) C6 0.0720(11) 0.0453(8) 0.0442(8) 0.0085(6) 0.0294(8) 0.0171(8) P1 0.02426(17) 0.03040(18) 0.02793(18) -0.00079(11) -0.00025(12) -0.00189(10) F11 0.0494(5) 0.0388(5) 0.0543(5) 0.0155(4) -0.0092(4) -0.0015(4) F12 0.0495(5) 0.0317(4) 0.0477(5) 0.0059(3) 0.0117(4) -0.0006(3) F13 0.0411(5) 0.0477(5) 0.0354(4) -0.0108(3) 0.0006(3) 0.0089(4) F14 0.0455(5) 0.0604(6) 0.0318(4) -0.0117(4) 0.0058(3) -0.0128(4) F15 0.0244(4) 0.0623(6) 0.0529(5) -0.0032(4) -0.0004(4) -0.0047(4) F16 0.0243(4) 0.0416(5) 0.0464(5) -0.0031(3) 0.0011(3) -0.0026(3) C1S 0.0925(14) 0.0383(8) 0.0310(7) -0.0018(6) 0.0072(8) -0.0182(8) C2S 0.0679(12) 0.0489(9) 0.0533(10) 0.0092(7) -0.0218(9) -0.0136(8) C3S 0.0617(11) 0.0423(8) 0.0689(12) 0.0024(8) 0.0163(9) -0.0044(8) _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 C1 N1 1.461(2) . ? N1 C2 1.3248(16) . ? N1 C5 1.366(2) . ? C2 N3 1.3169(17) . ? N3 C4 1.3707(19) . ? N3 C6 1.4626(19) . ? C4 C5 1.336(3) . ? P1 F11 1.5941(9) . ? P1 F12 1.5952(9) . ? P1 F16 1.5988(8) . ? P1 F15 1.6012(9) . ? P1 F14 1.6028(9) . ? P1 F13 1.6102(9) . ? C1S C2S 1.369(3) . ? C1S C3S 1.373(3) 3_656 ? C2S C3S 1.388(3) . ? C3S C1S 1.373(3) 3_656 ? 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 C2 N1 C5 108.19(12) . . ? C2 N1 C1 125.56(15) . . ? C5 N1 C1 126.22(15) . . ? N3 C2 N1 109.02(12) . . ? C2 N3 C4 108.14(12) . . ? C2 N3 C6 125.13(13) . . ? C4 N3 C6 126.69(14) . . ? C5 C4 N3 107.37(13) . . ? C4 C5 N1 107.27(13) . . ? F11 P1 F12 179.15(5) . . ? F11 P1 F16 90.32(5) . . ? F12 P1 F16 89.86(5) . . ? F11 P1 F15 89.69(5) . . ? F12 P1 F15 90.12(5) . . ? F16 P1 F15 179.64(5) . . ? F11 P1 F14 90.68(6) . . ? F12 P1 F14 90.15(5) . . ? F16 P1 F14 90.23(5) . . ? F15 P1 F14 90.13(5) . . ? F11 P1 F13 89.63(5) . . ? F12 P1 F13 89.55(5) . . ? F16 P1 F13 89.54(5) . . ? F15 P1 F13 90.10(5) . . ? F14 P1 F13 179.61(6) . . ? C2S C1S C3S 120.01(16) . 3_656 ? C1S C2S C3S 120.15(16) . . ? C1S C3S C2S 119.84(18) 3_656 . ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 29.33 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.773 _refine_diff_density_min -0.340 _refine_diff_density_rms 0.145 #===END