# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Wesley Henderson' 'De Long,Hugh C.' 'Douglas Fox' 'Paul C. Trulove' 'Young Junior,Victor G.' _publ_contact_author_name 'Wesley Henderson' _publ_contact_author_address ; Chemistry US Naval Academy 572 M Holloway Road (Stop 9B) Annapolis Maryland 21402 UNITED STATES OF AMERICA ; _publ_contact_author_email HENDERSO@USNA.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; Alkyl vs. Alkoxy Chains on Ionic Liquid Cations ; data_06061a _database_code_depnum_ccdc_archive 'CCDC 606677' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-methoxyethyl)-2,3-dimethylimidazolium chloride ; _chemical_name_common 06061a _chemical_melting_point ? _chemical_formula_moiety 'C8 H15 N2 O, Cl' _chemical_formula_sum 'C8 H15 Cl N2 O' _chemical_formula_weight 190.67 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' 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' 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3748(13) _cell_length_b 7.5274(13) _cell_length_c 10.1293(18) _cell_angle_alpha 82.170(3) _cell_angle_beta 76.176(3) _cell_angle_gamma 65.881(3) _cell_volume 497.88(15) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2332 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 27.42 _exptl_crystal_description Irregular _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8754 _exptl_absorpt_correction_T_max 0.9505 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details 'Dr. W. Henderson / Prof. P. Trulove - USNA' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 5689 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.14 _reflns_number_total 2177 _reflns_number_gt 2039 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0521P)^2^+0.1388P] 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 2177 _refine_ls_number_parameters 112 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0312 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0857 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Cl1 Cl 0.33375(4) 0.33631(4) 0.28992(3) 0.03076(12) Uani 1 1 d . . . O1 O 0.02202(14) 0.08208(14) 0.74337(10) 0.0348(2) Uani 1 1 d . . . N1 N 0.30048(14) 0.25109(14) 0.75244(10) 0.0233(2) Uani 1 1 d . . . N2 N 0.25431(15) 0.46710(15) 0.89014(10) 0.0261(2) Uani 1 1 d . . . C1 C 0.25672(16) 0.44054(17) 0.76162(12) 0.0236(2) Uani 1 1 d . . . C2 C 0.29799(19) 0.29133(19) 0.96364(12) 0.0301(3) Uani 1 1 d . . . H2A H 0.3064 0.2697 1.0570 0.036 Uiso 1 1 calc R . . C3 C 0.32638(19) 0.15635(18) 0.87751(12) 0.0290(3) Uani 1 1 d . . . H3A H 0.3582 0.0214 0.8988 0.035 Uiso 1 1 calc R . . C4 C 0.30674(18) 0.15623(17) 0.63313(12) 0.0272(3) Uani 1 1 d . . . H4A H 0.3962 0.0164 0.6384 0.033 Uiso 1 1 calc R . . H4B H 0.3644 0.2159 0.5495 0.033 Uiso 1 1 calc R . . C5 C 0.09769(19) 0.17623(18) 0.62532(12) 0.0293(3) Uani 1 1 d . . . H5A H 0.0068 0.3157 0.6206 0.035 Uiso 1 1 calc R . . H5B H 0.1041 0.1155 0.5427 0.035 Uiso 1 1 calc R . . C6 C -0.1811(2) 0.1081(2) 0.74901(18) 0.0433(3) Uani 1 1 d . . . H6A H -0.2329 0.0533 0.8360 0.065 Uiso 1 1 calc R . . H6B H -0.1859 0.0414 0.6741 0.065 Uiso 1 1 calc R . . H6C H -0.2651 0.2474 0.7409 0.065 Uiso 1 1 calc R . . C7 C 0.2151(2) 0.59286(18) 0.65093(14) 0.0339(3) Uani 1 1 d . . . H7A H 0.2731 0.6863 0.6587 0.051 Uiso 1 1 calc R . . H7B H 0.0682 0.6609 0.6582 0.051 Uiso 1 1 calc R . . H7C H 0.2764 0.5323 0.5627 0.051 Uiso 1 1 calc R . . C8 C 0.2218(2) 0.6508(2) 0.94475(15) 0.0360(3) Uani 1 1 d . . . H8A H 0.1074 0.7567 0.9131 0.054 Uiso 1 1 calc R . . H8B H 0.3444 0.6785 0.9132 0.054 Uiso 1 1 calc R . . H8C H 0.1920 0.6399 1.0444 0.054 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 Cl1 0.03469(18) 0.03040(18) 0.02295(17) -0.00114(11) -0.00648(12) -0.00816(13) O1 0.0347(5) 0.0339(5) 0.0373(5) 0.0027(4) -0.0094(4) -0.0152(4) N1 0.0241(5) 0.0244(5) 0.0198(5) -0.0002(4) -0.0056(4) -0.0075(4) N2 0.0250(5) 0.0307(5) 0.0241(5) -0.0044(4) -0.0039(4) -0.0119(4) C1 0.0207(5) 0.0258(5) 0.0237(5) -0.0015(4) -0.0043(4) -0.0084(4) C2 0.0324(6) 0.0391(7) 0.0213(5) 0.0022(5) -0.0071(5) -0.0165(5) C3 0.0335(6) 0.0297(6) 0.0242(6) 0.0055(5) -0.0096(5) -0.0128(5) C4 0.0311(6) 0.0266(6) 0.0203(5) -0.0049(4) -0.0040(4) -0.0071(5) C5 0.0360(6) 0.0282(6) 0.0244(6) -0.0036(5) -0.0106(5) -0.0099(5) C6 0.0370(7) 0.0406(8) 0.0566(9) -0.0102(7) -0.0079(6) -0.0179(6) C7 0.0433(7) 0.0275(6) 0.0323(7) 0.0054(5) -0.0143(6) -0.0137(5) C8 0.0362(7) 0.0371(7) 0.0385(7) -0.0142(6) -0.0037(5) -0.0165(5) _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 C6 1.4173(17) . ? O1 C5 1.4203(16) . ? N1 C1 1.3387(15) . ? N1 C3 1.3813(15) . ? N1 C4 1.4677(15) . ? N2 C1 1.3386(15) . ? N2 C2 1.3808(16) . ? N2 C8 1.4661(16) . ? C1 C7 1.4808(16) . ? C2 C3 1.3483(18) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.5070(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 C6 O1 C5 111.74(11) . . ? C1 N1 C3 109.32(10) . . ? C1 N1 C4 126.69(10) . . ? C3 N1 C4 123.85(10) . . ? C1 N2 C2 109.52(10) . . ? C1 N2 C8 126.04(11) . . ? C2 N2 C8 124.36(11) . . ? N2 C1 N1 107.20(10) . . ? N2 C1 C7 126.40(11) . . ? N1 C1 C7 126.40(11) . . ? C3 C2 N2 106.85(11) . . ? C3 C2 H2A 126.6 . . ? N2 C2 H2A 126.6 . . ? C2 C3 N1 107.11(11) . . ? C2 C3 H3A 126.4 . . ? N1 C3 H3A 126.4 . . ? N1 C4 C5 111.12(9) . . ? N1 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N1 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? O1 C5 C4 108.34(10) . . ? O1 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? O1 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? O1 C6 H6A 109.5 . . ? O1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C2 N2 C1 N1 0.21(12) . . . . ? C8 N2 C1 N1 177.08(10) . . . . ? C2 N2 C1 C7 179.20(11) . . . . ? C8 N2 C1 C7 -3.93(19) . . . . ? C3 N1 C1 N2 -0.07(12) . . . . ? C4 N1 C1 N2 175.80(10) . . . . ? C3 N1 C1 C7 -179.06(11) . . . . ? C4 N1 C1 C7 -3.19(18) . . . . ? C1 N2 C2 C3 -0.27(13) . . . . ? C8 N2 C2 C3 -177.20(11) . . . . ? N2 C2 C3 N1 0.22(13) . . . . ? C1 N1 C3 C2 -0.10(13) . . . . ? C4 N1 C3 C2 -176.11(10) . . . . ? C1 N1 C4 C5 -83.18(14) . . . . ? C3 N1 C4 C5 92.13(13) . . . . ? C6 O1 C5 C4 175.24(10) . . . . ? N1 C4 C5 O1 -61.63(13) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.283 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.044 #===END data_06062c _database_code_depnum_ccdc_archive 'CCDC 606678' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-(2-methoxyethyl)-2,3-dimethylimidazolium hexafluorophosphate ; _chemical_name_common 06062a _chemical_melting_point ? _chemical_formula_moiety 'C8 H15 N2 O, F6 P' _chemical_formula_sum 'C8 H15 F6 N2 O P' _chemical_formula_weight 300.19 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' 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3405(13) _cell_length_b 8.7297(14) _cell_length_c 10.4831(16) _cell_angle_alpha 67.755(2) _cell_angle_beta 69.073(2) _cell_angle_gamma 62.821(2) _cell_volume 612.52(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2361 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 27.11 _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.628 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 0.291 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9049 _exptl_absorpt_correction_T_max 0.9307 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 2003)' _exptl_special_details 'Dr. W. Henderson / Prof. P. Trulove - USNA' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '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 6573 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.15 _reflns_number_total 2665 _reflns_number_gt 2354 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0622P)^2^+0.2110P] 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 2665 _refine_ls_number_parameters 248 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1057 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.084 _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 O1 O 0.47591(17) 0.65286(15) 0.59879(12) 0.0368(3) Uani 1 1 d . . . N1 N 0.76908(17) 0.31234(16) 0.69093(13) 0.0263(3) Uani 1 1 d . . . N2 N 1.03881(17) 0.26543(17) 0.70566(14) 0.0301(3) Uani 1 1 d . . . C1 C 0.8662(2) 0.28508(18) 0.77965(15) 0.0268(3) Uani 1 1 d . . . C2 C 1.0510(2) 0.2795(2) 0.56751(17) 0.0342(3) Uani 1 1 d . . . H2A H 1.1584 0.2705 0.4929 0.041 Uiso 1 1 calc R . . C3 C 0.8835(2) 0.3081(2) 0.55810(16) 0.0321(3) Uani 1 1 d . . . H3A H 0.8495 0.3229 0.4756 0.039 Uiso 1 1 calc R . . C4 C 0.5708(2) 0.3469(2) 0.72594(18) 0.0320(3) Uani 1 1 d . . . H4A H 0.5402 0.2637 0.8175 0.038 Uiso 1 1 calc R . . H4B H 0.5423 0.3237 0.6526 0.038 Uiso 1 1 calc R . . C5 C 0.4522(2) 0.5363(2) 0.73564(17) 0.0316(3) Uani 1 1 d . . . H5A H 0.3206 0.5500 0.7728 0.038 Uiso 1 1 calc R . . H5B H 0.4891 0.5655 0.8008 0.038 Uiso 1 1 calc R . . C6 C 0.3724(3) 0.8340(2) 0.6028(2) 0.0440(4) Uani 1 1 d . . . H6A H 0.3849 0.9115 0.5065 0.066 Uiso 1 1 calc R . . H6B H 0.4192 0.8640 0.6601 0.066 Uiso 1 1 calc R . . H6C H 0.2418 0.8513 0.6447 0.066 Uiso 1 1 calc R . . C7 C 0.7985(3) 0.2743(2) 0.93277(16) 0.0372(4) Uani 1 1 d . . . H7A H 0.6890 0.2424 0.9693 0.056 Uiso 1 1 calc R . . H7B H 0.7662 0.3900 0.9478 0.056 Uiso 1 1 calc R . . H7C H 0.8957 0.1832 0.9826 0.056 Uiso 1 1 calc R . . C8 C 1.1900(2) 0.2404(3) 0.7603(2) 0.0462(4) Uani 1 1 d . . . H8A H 1.1506 0.3350 0.8061 0.069 Uiso 1 1 calc R . . H8B H 1.2975 0.2453 0.6821 0.069 Uiso 1 1 calc R . . H8C H 1.2234 0.1242 0.8293 0.069 Uiso 1 1 calc R . . P1 P 0.7819(3) 0.8032(3) 0.8237(2) 0.02572(16) Uani 0.509(4) 1 d PD A 1 F1 F 0.5804(4) 0.9368(5) 0.8082(6) 0.0778(13) Uani 0.509(4) 1 d PD A 1 F2 F 0.8634(7) 0.9104(6) 0.6756(3) 0.0706(17) Uani 0.509(4) 1 d PD A 1 F3 F 0.7686(9) 0.6817(6) 0.7507(5) 0.0560(13) Uani 0.509(4) 1 d PD A 1 F4 F 0.7929(8) 0.9238(6) 0.8973(5) 0.0525(11) Uani 0.509(4) 1 d PD A 1 F5 F 0.7017(6) 0.6949(6) 0.9721(3) 0.0623(14) Uani 0.509(4) 1 d PD A 1 F6 F 0.9830(3) 0.6686(5) 0.8381(6) 0.0870(18) Uani 0.509(4) 1 d PD A 1 P1' P 0.7785(4) 0.8010(5) 0.8287(4) 0.02572(16) Uani 0.338(6) 1 d PD B 2 F1' F 0.7170(12) 0.7020(10) 0.7668(8) 0.072(3) Uani 0.338(6) 1 d PD B 2 F2' F 0.7923(10) 0.9420(8) 0.6813(5) 0.0504(16) Uani 0.338(6) 1 d PD B 2 F3' F 0.9857(6) 0.6805(10) 0.7806(7) 0.077(2) Uani 0.338(6) 1 d PD B 2 F4' F 0.5702(5) 0.9204(9) 0.8751(7) 0.077(2) Uani 0.338(6) 1 d PD B 2 F5' F 0.7635(12) 0.6594(8) 0.9755(5) 0.0504(16) Uani 0.338(6) 1 d PD B 2 F6' F 0.8408(12) 0.8989(11) 0.8897(8) 0.072(3) Uani 0.338(6) 1 d PD B 2 P1" P 0.7816(8) 0.7932(8) 0.8387(6) 0.02572(16) Uani 0.153(5) 1 d PD C 3 F1" F 0.5922(15) 0.767(3) 0.887(2) 0.177(9) Uani 0.153(5) 1 d PD C 3 F2" F 0.716(3) 0.9459(13) 0.7062(12) 0.105(7) Uani 0.153(5) 1 d PD C 3 F3" F 0.867(3) 0.6518(13) 0.7502(11) 0.117(10) Uani 0.153(5) 1 d PD C 3 F4" F 0.696(3) 0.9345(13) 0.9269(11) 0.117(10) Uani 0.153(5) 1 d PD C 3 F5" F 0.846(3) 0.6396(13) 0.9709(11) 0.105(7) Uani 0.153(5) 1 d PD C 3 F6" F 0.9707(15) 0.819(3) 0.790(2) 0.177(9) Uani 0.153(5) 1 d PD C 3 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 0.0466(7) 0.0274(6) 0.0330(6) -0.0069(5) -0.0120(5) -0.0095(5) N1 0.0284(6) 0.0238(6) 0.0283(6) -0.0075(5) -0.0064(5) -0.0103(5) N2 0.0276(6) 0.0276(6) 0.0353(7) -0.0101(5) -0.0075(5) -0.0086(5) C1 0.0299(7) 0.0216(6) 0.0284(7) -0.0072(5) -0.0068(6) -0.0086(5) C2 0.0362(8) 0.0319(8) 0.0302(8) -0.0116(6) 0.0007(6) -0.0123(6) C3 0.0417(8) 0.0295(7) 0.0254(7) -0.0089(6) -0.0065(6) -0.0127(6) C4 0.0287(7) 0.0301(7) 0.0400(8) -0.0073(6) -0.0088(6) -0.0138(6) C5 0.0279(7) 0.0312(8) 0.0329(8) -0.0080(6) -0.0053(6) -0.0100(6) C6 0.0504(10) 0.0283(8) 0.0528(11) -0.0076(7) -0.0191(8) -0.0110(7) C7 0.0474(9) 0.0358(8) 0.0258(7) -0.0086(6) -0.0067(7) -0.0141(7) C8 0.0331(9) 0.0508(11) 0.0597(12) -0.0169(9) -0.0177(8) -0.0123(8) P1 0.0279(2) 0.0244(2) 0.0228(3) -0.0050(2) -0.00589(19) -0.00869(17) F1 0.0474(18) 0.064(2) 0.115(4) -0.024(2) -0.048(2) 0.0064(16) F2 0.108(4) 0.064(3) 0.0426(17) -0.0094(15) 0.0134(19) -0.060(3) F3 0.104(3) 0.0424(19) 0.0361(16) -0.0133(14) -0.0110(19) -0.040(2) F4 0.097(3) 0.0376(15) 0.0369(19) -0.0106(13) -0.0260(18) -0.0276(18) F5 0.088(3) 0.057(2) 0.0335(16) -0.0093(13) 0.0152(16) -0.043(2) F6 0.0331(15) 0.0566(19) 0.150(5) -0.022(3) -0.030(2) 0.0037(14) P1' 0.0279(2) 0.0244(2) 0.0228(3) -0.0050(2) -0.00589(19) -0.00869(17) F1' 0.112(6) 0.084(4) 0.067(4) -0.004(3) -0.044(4) -0.069(4) F2' 0.097(5) 0.0307(19) 0.0205(16) 0.0050(13) -0.0193(18) -0.026(2) F3' 0.0342(19) 0.084(3) 0.072(3) -0.031(3) 0.0019(16) 0.0097(18) F4' 0.0342(19) 0.084(3) 0.072(3) -0.031(3) 0.0019(16) 0.0097(18) F5' 0.097(5) 0.0307(19) 0.0205(16) 0.0050(13) -0.0193(18) -0.026(2) F6' 0.112(6) 0.084(4) 0.067(4) -0.004(3) -0.044(4) -0.069(4) P1" 0.0279(2) 0.0244(2) 0.0228(3) -0.0050(2) -0.00589(19) -0.00869(17) F1" 0.056(7) 0.193(19) 0.29(2) -0.072(18) 0.010(10) -0.078(10) F2" 0.183(19) 0.049(5) 0.087(9) 0.005(5) -0.096(11) -0.015(7) F3" 0.22(2) 0.037(4) 0.036(4) -0.023(3) -0.001(8) -0.009(8) F4" 0.22(2) 0.037(4) 0.036(4) -0.023(3) -0.001(8) -0.009(8) F5" 0.183(19) 0.049(5) 0.087(9) 0.005(5) -0.096(11) -0.015(7) F6" 0.056(7) 0.193(19) 0.29(2) -0.072(18) 0.010(10) -0.078(10) _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 C5 1.4172(18) . ? O1 C6 1.423(2) . ? N1 C1 1.3311(19) . ? N1 C3 1.3815(19) . ? N1 C4 1.4683(18) . ? N2 C1 1.3348(19) . ? N2 C2 1.376(2) . ? N2 C8 1.461(2) . ? C1 C7 1.480(2) . ? C2 C3 1.336(2) . ? C2 H2A 0.9500 . ? C3 H3A 0.9500 . ? C4 C5 1.512(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? P1 F6 1.569(2) . ? P1 F4 1.570(2) . ? P1 F1 1.572(2) . ? P1 F2 1.574(2) . ? P1 F5 1.576(2) . ? P1 F3 1.584(2) . ? P1' F3' 1.570(3) . ? P1' F6' 1.571(3) . ? P1' F4' 1.571(3) . ? P1' F2' 1.574(3) . ? P1' F5' 1.574(3) . ? P1' F1' 1.580(3) . ? P1" F6" 1.571(3) . ? P1" F4" 1.573(3) . ? P1" F1" 1.573(3) . ? P1" F5" 1.574(3) . ? P1" F2" 1.574(3) . ? P1" F3" 1.576(3) . ? 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 C5 O1 C6 110.97(13) . . ? C1 N1 C3 109.17(13) . . ? C1 N1 C4 126.00(13) . . ? C3 N1 C4 124.81(13) . . ? C1 N2 C2 109.28(13) . . ? C1 N2 C8 125.72(14) . . ? C2 N2 C8 124.96(14) . . ? N1 C1 N2 107.32(13) . . ? N1 C1 C7 126.93(14) . . ? N2 C1 C7 125.73(14) . . ? C3 C2 N2 107.15(14) . . ? C3 C2 H2A 126.4 . . ? N2 C2 H2A 126.4 . . ? C2 C3 N1 107.08(14) . . ? C2 C3 H3A 126.5 . . ? N1 C3 H3A 126.5 . . ? N1 C4 C5 112.19(12) . . ? N1 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N1 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? O1 C5 C4 108.67(13) . . ? O1 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? O1 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.3 . . ? O1 C6 H6A 109.5 . . ? O1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C1 C7 H7A 109.5 . . ? C1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? F6 P1 F4 90.63(16) . . ? F6 P1 F1 179.3(2) . . ? F4 P1 F1 90.09(16) . . ? F6 P1 F2 89.81(17) . . ? F4 P1 F2 89.85(16) . . ? F1 P1 F2 90.10(17) . . ? F6 P1 F5 89.82(17) . . ? F4 P1 F5 90.21(15) . . ? F1 P1 F5 90.28(17) . . ? F2 P1 F5 179.6(2) . . ? F6 P1 F3 89.80(16) . . ? F4 P1 F3 179.35(18) . . ? F1 P1 F3 89.47(16) . . ? F2 P1 F3 90.64(15) . . ? F5 P1 F3 89.30(15) . . ? F3' P1' F6' 90.3(2) . . ? F3' P1' F4' 179.0(2) . . ? F6' P1' F4' 90.7(2) . . ? F3' P1' F2' 89.9(2) . . ? F6' P1' F2' 90.05(19) . . ? F4' P1' F2' 89.90(19) . . ? F3' P1' F5' 90.3(2) . . ? F6' P1' F5' 90.51(19) . . ? F4' P1' F5' 89.9(2) . . ? F2' P1' F5' 179.4(2) . . ? F3' P1' F1' 89.3(2) . . ? F6' P1' F1' 179.6(3) . . ? F4' P1' F1' 89.7(2) . . ? F2' P1' F1' 89.89(19) . . ? F5' P1' F1' 89.56(19) . . ? F6" P1" F4" 90.1(2) . . ? F6" P1" F1" 180.0(4) . . ? F4" P1" F1" 90.0(2) . . ? F6" P1" F5" 90.2(2) . . ? F4" P1" F5" 90.3(2) . . ? F1" P1" F5" 89.8(2) . . ? F6" P1" F2" 90.2(2) . . ? F4" P1" F2" 90.1(2) . . ? F1" P1" F2" 89.8(2) . . ? F5" P1" F2" 179.5(3) . . ? F6" P1" F3" 90.0(2) . . ? F4" P1" F3" 179.9(3) . . ? F1" P1" F3" 90.0(2) . . ? F5" P1" F3" 89.7(2) . . ? F2" P1" F3" 89.9(2) . . ? 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 C3 N1 C1 N2 0.57(16) . . . . ? C4 N1 C1 N2 -177.75(13) . . . . ? C3 N1 C1 C7 -178.22(14) . . . . ? C4 N1 C1 C7 3.5(2) . . . . ? C2 N2 C1 N1 -0.38(16) . . . . ? C8 N2 C1 N1 177.24(14) . . . . ? C2 N2 C1 C7 178.42(14) . . . . ? C8 N2 C1 C7 -4.0(2) . . . . ? C1 N2 C2 C3 0.05(18) . . . . ? C8 N2 C2 C3 -177.59(15) . . . . ? N2 C2 C3 N1 0.29(17) . . . . ? C1 N1 C3 C2 -0.54(17) . . . . ? C4 N1 C3 C2 177.80(13) . . . . ? C1 N1 C4 C5 76.98(18) . . . . ? C3 N1 C4 C5 -101.08(17) . . . . ? C6 O1 C5 C4 -177.76(13) . . . . ? N1 C4 C5 O1 67.82(16) . . . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.287 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.058 #===END