Supplementary Material for Dalton Transactions This journal is (c) The Royal Society of Chemsitry 2002 data_global _journal_coden_Cambridge 186 loop_ _publ_author_name 'Esterhuysen, Catherine' 'Raubenheimer, Helgard G.' 'Stenzel, Oleg' _audit_creation_method SHELXL-97 #'SHELXL-97 plus manual edit of cif file' _publ_contact_author_name 'Prof. Helgard Raubenheimer' _publ_contact_author_address ; Department of Chemistry University of Stellenbosch Private Bag X1 Matieland, 7602 South Africa ; _publ_contact_author_phone '+27 21 808 3850' _publ_contact_author_fax '+27 21 808 3849' _publ_contact_author_email 'hgr@sun.ac.za' _publ_requested_journal ; Journal of the Chemical Society, Dalton Transactions ; _publ_section_title ; Biphasic Hydroformylations in New Molten Salts - Analogies and Differences to Organic Solvents ; _publ_section_references ; Farrugia, L.J. (1997). J. Appl. Cryst. 30, 565. Nonius BV (1998) COLLECT. Data collection software. Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997) Methods Enzymol., 276, 307. Sheldrick, G.M. (1997). SHELX-97. Program for crystal structure analysis. Univ. of G\"ottingen, Germany. ; _publ_section_figure_captions ; Fig. 1: The molecular conformation of the title compound. Ellipsoids are shown at the 50% probability level. ; data_1 _database_code_CSD 169677 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2,3-trimethylimidazolium triflate ; _chemical_name_common ? _chemical_formula_moiety 'C6 H11 N2, C F3 O3 S' _chemical_formula_sum 'C7 H11 F3 N2 O3 S1' _chemical_formula_weight 260.23 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' 'F' 'F' 0.0171 0.0103 '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/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 6.8313(2) _cell_length_b 14.4530(5) _cell_length_c 11.3689(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.503(2) _cell_angle_gamma 90.00 _cell_volume 1115.26(6) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 1972 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.327 _exptl_absorpt_correction_type none _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 'Nonius Kappa CCD' _diffrn_measurement_method '\f and \w scans to fill Ewald sphere' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5124 _diffrn_reflns_av_R_equivalents 0.0201 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.39 _reflns_number_total 2524 _reflns_number_gt 1977 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III for Windows (Farrugia,1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0495P)^2^+0.7809P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2524 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1149 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.002 _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 S1 S 0.13829(7) 0.38063(3) 0.22434(4) 0.02547(16) Uani 1 1 d . . . F1 F -0.1404(2) 0.30263(10) 0.08098(13) 0.0520(4) Uani 1 1 d . . . F2 F -0.1422(2) 0.45069(10) 0.07470(12) 0.0490(4) Uani 1 1 d . . . F3 F -0.2447(2) 0.38078(11) 0.22208(16) 0.0597(5) Uani 1 1 d . . . O1 O 0.2615(2) 0.37683(11) 0.13016(15) 0.0401(4) Uani 1 1 d . . . O2 O 0.1443(2) 0.46734(11) 0.28732(13) 0.0392(4) Uani 1 1 d . . . O3 O 0.1426(3) 0.30022(11) 0.29829(15) 0.0480(5) Uani 1 1 d . . . N1 N 0.1275(3) 0.37063(12) 0.62806(16) 0.0320(4) Uani 1 1 d . . . N2 N 0.3661(3) 0.40154(12) 0.76219(15) 0.0305(4) Uani 1 1 d . . . C1 C 0.0790(4) 0.32073(17) 0.8320(2) 0.0438(6) Uani 1 1 d . . . H1A H -0.0473 0.2974 0.7939 0.066 Uiso 1 1 calc R . . H1B H 0.0551 0.3671 0.8915 0.066 Uiso 1 1 calc R . . H1C H 0.1553 0.2694 0.8702 0.066 Uiso 1 1 calc R . . C2 C 0.1896(3) 0.36301(14) 0.74242(19) 0.0298(5) Uani 1 1 d . . . C3 C 0.4937(3) 0.40603(15) 0.87465(19) 0.0329(5) Uani 1 1 d . . . H31 H 0.4125 0.4087 0.9403 0.057(8) Uiso 1 1 calc R . . H32 H 0.5765 0.4615 0.8758 0.062(8) Uiso 1 1 calc R . . H33 H 0.5777 0.3509 0.8831 0.039(6) Uiso 1 1 calc R . . C4 C 0.4184(4) 0.43510(16) 0.6554(2) 0.0394(5) Uani 1 1 d . . . H4 H 0.5377 0.4659 0.6439 0.051(7) Uiso 1 1 calc R . . C5 C 0.2717(4) 0.41627(16) 0.5729(2) 0.0392(5) Uani 1 1 d . . . H5 H 0.2657 0.4311 0.4912 0.056(8) Uiso 1 1 calc R . . C6 C -0.0602(3) 0.33843(17) 0.5670(2) 0.0393(5) Uani 1 1 d . . . H61 H -0.0514 0.3359 0.4816 0.088(11) Uiso 1 1 calc R . . H62 H -0.1654 0.3812 0.5828 0.086(12) Uiso 1 1 calc R . . H63 H -0.0895 0.2766 0.5956 0.110(14) Uiso 1 1 calc R . . C7 C -0.1100(3) 0.37855(14) 0.1468(2) 0.0319(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 S1 0.0257(3) 0.0260(3) 0.0243(3) 0.00017(19) 0.00099(18) 0.00185(19) F1 0.0564(9) 0.0403(8) 0.0560(9) -0.0123(7) -0.0083(7) -0.0183(7) F2 0.0481(9) 0.0426(8) 0.0511(9) 0.0115(7) -0.0174(7) 0.0032(6) F3 0.0314(8) 0.0764(12) 0.0747(11) -0.0001(9) 0.0202(8) -0.0031(7) O1 0.0337(9) 0.0502(10) 0.0388(9) -0.0045(7) 0.0137(7) 0.0002(7) O2 0.0429(9) 0.0360(8) 0.0369(9) -0.0129(7) -0.0027(7) -0.0017(7) O3 0.0589(12) 0.0394(9) 0.0447(10) 0.0172(8) 0.0017(8) 0.0098(8) N1 0.0331(10) 0.0305(9) 0.0310(9) -0.0076(7) -0.0023(8) 0.0016(7) N2 0.0309(9) 0.0302(9) 0.0297(9) -0.0044(7) 0.0005(7) 0.0003(7) C1 0.0516(15) 0.0410(13) 0.0420(13) 0.0030(11) 0.0197(11) -0.0063(11) C2 0.0318(11) 0.0263(10) 0.0312(11) -0.0052(8) 0.0038(9) 0.0023(8) C3 0.0313(11) 0.0376(11) 0.0284(11) -0.0055(9) -0.0031(9) -0.0008(9) C4 0.0425(13) 0.0414(13) 0.0366(12) -0.0002(10) 0.0147(10) -0.0108(10) C5 0.0523(15) 0.0382(12) 0.0282(11) 0.0020(10) 0.0101(10) -0.0051(11) C6 0.0337(12) 0.0444(13) 0.0375(13) -0.0095(11) -0.0059(10) -0.0063(10) C7 0.0286(11) 0.0291(10) 0.0375(12) -0.0003(9) 0.0016(9) -0.0035(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 S1 O3 1.4327(16) . ? S1 O1 1.4358(16) . ? S1 O2 1.4417(15) . ? S1 C7 1.821(2) . ? F1 C7 1.331(2) . ? F2 C7 1.329(2) . ? F3 C7 1.326(3) . ? N1 C2 1.326(3) . ? N1 C5 1.392(3) . ? N1 C6 1.463(3) . ? N2 C2 1.324(3) . ? N2 C4 1.391(3) . ? N2 C3 1.465(3) . ? C1 C2 1.468(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 H31 0.9800 . ? C3 H32 0.9800 . ? C3 H33 0.9800 . ? C4 C5 1.321(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H61 0.9800 . ? C6 H62 0.9800 . ? C6 H63 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 O3 S1 O1 115.59(10) . . ? O3 S1 O2 114.59(10) . . ? O1 S1 O2 114.67(10) . . ? O3 S1 C7 103.11(10) . . ? O1 S1 C7 103.33(10) . . ? O2 S1 C7 103.15(10) . . ? C2 N1 C5 108.47(18) . . ? C2 N1 C6 127.2(2) . . ? C5 N1 C6 124.30(19) . . ? C2 N2 C4 108.53(18) . . ? C2 N2 C3 127.40(19) . . ? C4 N2 C3 124.02(18) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 N1 108.40(19) . . ? N2 C2 C1 126.0(2) . . ? N1 C2 C1 125.6(2) . . ? N2 C3 H31 109.5 . . ? N2 C3 H32 109.5 . . ? H31 C3 H32 109.5 . . ? N2 C3 H33 109.5 . . ? H31 C3 H33 109.5 . . ? H32 C3 H33 109.5 . . ? C5 C4 N2 107.3(2) . . ? C5 C4 H4 126.3 . . ? N2 C4 H4 126.3 . . ? C4 C5 N1 107.25(19) . . ? C4 C5 H5 126.4 . . ? N1 C5 H5 126.4 . . ? N1 C6 H61 109.5 . . ? N1 C6 H62 109.5 . . ? H61 C6 H62 109.5 . . ? N1 C6 H63 109.5 . . ? H61 C6 H63 109.5 . . ? H62 C6 H63 109.5 . . ? F3 C7 F2 107.47(18) . . ? F3 C7 F1 107.90(17) . . ? F2 C7 F1 107.21(18) . . ? F3 C7 S1 111.30(16) . . ? F2 C7 S1 111.46(14) . . ? F1 C7 S1 111.29(15) . . ? _diffrn_reflns_theta_full 27.39 _refine_diff_density_max 0.518 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.058 #===END data_2 _database_code_CSD 169678 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-ethyl-2,3-dimethylimidazolium triflate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C7 H13 N2),2(C F3 S O3)' _chemical_formula_sum 'C16 H26 F6 N4 O6 S2' _chemical_formula_weight 548.52 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' 'F' 'F' 0.0171 0.0103 '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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/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 15.7220(10) _cell_length_b 8.6150(10) _cell_length_c 18.0810(10) _cell_angle_alpha 90.000 _cell_angle_beta 89.979(11) _cell_angle_gamma 90.000 _cell_volume 2449.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 172(2) _cell_measurement_reflns_used 2497 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.41 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.302 _exptl_absorpt_correction_type none _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 'Nonius Kappa CCD' _diffrn_measurement_method '\f and \w scans to fill Ewald sphere' _diffrn_reflns_number 8798 _diffrn_reflns_av_R_equivalents 0.0189 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4027 _reflns_number_gt 3411 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III for Windows (Farrugia,1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0552P)^2^+0.8939P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4027 _refine_ls_number_parameters 428 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0503 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1027 _refine_ls_wR_factor_gt 0.0969 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.055 _refine_ls_shift/su_mean 0.003 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 S1 S 0.12301(7) 0.20255(7) -0.13493(4) 0.03398(19) Uani 1 1 d . . . O11 O 0.1218(2) 0.3689(2) -0.13018(14) 0.0629(6) Uani 1 1 d . . . O12 O 0.04735(18) 0.1371(4) -0.16498(16) 0.0653(8) Uani 1 1 d . . . O13 O 0.20125(17) 0.1399(3) -0.16009(16) 0.0619(7) Uani 1 1 d . . . F11 F 0.1212(2) -0.0104(2) -0.03313(12) 0.0838(7) Uani 1 1 d . . . F12 F 0.18500(17) 0.1978(3) -0.00138(15) 0.0829(8) Uani 1 1 d . . . F13 F 0.04996(17) 0.1911(4) -0.00623(16) 0.0971(10) Uani 1 1 d . . . C1 C 0.1196(3) 0.1434(4) -0.03969(17) 0.0486(8) Uani 1 1 d . . . S2 S 0.62453(7) 0.17433(7) -0.15753(4) 0.03308(19) Uani 1 1 d . . . O21 O 0.69928(16) 0.2585(4) -0.17471(15) 0.0619(8) Uani 1 1 d . . . O22 O 0.6237(2) 0.0185(2) -0.18569(12) 0.0599(6) Uani 1 1 d . . . O23 O 0.54553(16) 0.2535(3) -0.16758(15) 0.0603(8) Uani 1 1 d . . . F21 F 0.70213(17) 0.0763(3) -0.03828(14) 0.0849(8) Uani 1 1 d . . . F22 F 0.56720(19) 0.0654(4) -0.03367(16) 0.1089(12) Uani 1 1 d . . . F23 F 0.6302(2) 0.2825(3) -0.02383(12) 0.0967(9) Uani 1 1 d . . . C2 C 0.6305(3) 0.1464(4) -0.05876(18) 0.0535(9) Uani 1 1 d . . . N11A N 0.1081(7) 0.3177(10) -0.3277(4) 0.042(2) Uani 0.589(9) 1 d P A 1 C11A C 0.2431(6) 0.1724(10) -0.3366(6) 0.039(3) Uani 0.589(9) 1 d P A 1 H11A H 0.2645 0.2096 -0.2889 0.058 Uiso 0.589(9) 1 calc PR A 1 H11B H 0.2675 0.2354 -0.3765 0.058 Uiso 0.589(9) 1 calc PR A 1 H11C H 0.2596 0.0636 -0.3435 0.058 Uiso 0.589(9) 1 calc PR A 1 C12A C 0.1508(8) 0.1852(14) -0.3381(5) 0.042(3) Uani 0.589(9) 1 d P A 1 N12A N 0.0960(6) 0.0739(7) -0.3479(3) 0.0385(18) Uani 0.589(9) 1 d P A 1 C14A C 0.0137(6) 0.1383(11) -0.3477(5) 0.047(2) Uani 0.589(9) 1 d P A 1 H14A H -0.0381 0.0841 -0.3557 0.056 Uiso 0.589(9) 1 calc PR A 1 C15A C 0.0218(6) 0.2850(12) -0.3345(6) 0.039(2) Uani 0.589(9) 1 d P A 1 H15A H -0.0233 0.3579 -0.3302 0.046 Uiso 0.589(9) 1 calc PR A 1 N11B N 0.1588(7) 0.3207(10) -0.3280(4) 0.025(2) Uani 0.411(9) 1 d P A 2 C11B C 0.0077(8) 0.2185(14) -0.3390(8) 0.025(3) Uani 0.411(9) 1 d PU A 2 H11D H -0.0159 0.1799 -0.2923 0.038 Uiso 0.411(9) 1 calc PR A 2 H11E H -0.0156 0.1581 -0.3802 0.038 Uiso 0.411(9) 1 calc PR A 2 H11F H -0.0074 0.3280 -0.3453 0.038 Uiso 0.411(9) 1 calc PR A 2 C12B C 0.1031(9) 0.2021(13) -0.3379(5) 0.018(2) Uani 0.411(9) 1 d P A 2 N12B N 0.1473(7) 0.0737(13) -0.3479(5) 0.027(2) Uani 0.411(9) 1 d P A 2 C14B C 0.2343(9) 0.1045(12) -0.3393(9) 0.023(3) Uani 0.411(9) 1 d P A 2 H14B H 0.2796 0.0316 -0.3404 0.028 Uiso 0.411(9) 1 calc PR A 2 C15B C 0.2403(6) 0.2616(14) -0.3292(5) 0.023(2) Uani 0.411(9) 1 d P A 2 H15B H 0.2914 0.3194 -0.3239 0.028 Uiso 0.411(9) 1 calc PR A 2 C13 C 0.1405(3) 0.4780(3) -0.31516(19) 0.0466(10) Uani 1 1 d . . . H13A H 0.1712 0.4820 -0.2680 0.056 Uiso 1 1 calc R A 1 H13B H 0.0927 0.5508 -0.3138 0.056 Uiso 1 1 calc R A 1 H13C H 0.1792 0.5068 -0.3555 0.056 Uiso 1 1 calc R A 1 C16 C 0.1132(2) -0.0847(3) -0.36470(19) 0.0440(8) Uani 1 1 d . . . H16A H 0.0648 -0.1487 -0.3474 0.066 Uiso 1 1 calc R A 1 H16B H 0.1642 -0.1177 -0.3368 0.066 Uiso 1 1 calc R A 1 C17 C 0.1276(4) -0.1169(4) -0.4448(2) 0.0706(11) Uani 1 1 d . A . H17A H 0.0777 -0.0838 -0.4732 0.106 Uiso 1 1 calc R . . H17B H 0.1368 -0.2284 -0.4521 0.106 Uiso 1 1 calc R . . H17C H 0.1778 -0.0596 -0.4619 0.106 Uiso 1 1 calc R . . N21A N 0.5945(7) 0.3067(10) -0.3449(4) 0.040(2) Uani 0.572(9) 1 d P B 3 C21A C 0.7412(6) 0.2095(13) -0.3585(6) 0.048(3) Uani 0.572(9) 1 d P B 3 H21A H 0.7643 0.2109 -0.3082 0.072 Uiso 0.572(9) 1 calc PR B 3 H21B H 0.7554 0.3071 -0.3835 0.072 Uiso 0.572(9) 1 calc PR B 3 H21C H 0.7659 0.1224 -0.3860 0.072 Uiso 0.572(9) 1 calc PR B 3 C22A C 0.6494(10) 0.1919(13) -0.3554(5) 0.043(3) Uani 0.572(9) 1 d P B 3 N22A N 0.6064(7) 0.0629(9) -0.3616(4) 0.046(2) Uani 0.572(9) 1 d P B 3 C24A C 0.5207(5) 0.0964(10) -0.3575(5) 0.041(2) Uani 0.572(9) 1 d P B 3 H24A H 0.4758 0.0230 -0.3618 0.050 Uiso 0.572(9) 1 calc PR B 3 C25A C 0.5113(5) 0.2443(11) -0.3467(4) 0.038(2) Uani 0.572(9) 1 d P B 3 H25A H 0.4593 0.2994 -0.3412 0.045 Uiso 0.572(9) 1 calc PR B 3 N21B N 0.6435(7) 0.3170(11) -0.3470(5) 0.023(2) Uani 0.428(9) 1 d P B 4 C21B C 0.5058(8) 0.1659(13) -0.3499(8) 0.033(3) Uani 0.428(9) 1 d PU B 4 H21D H 0.4816 0.2471 -0.3183 0.050 Uiso 0.428(9) 1 calc PR B 4 H21E H 0.4915 0.0637 -0.3295 0.050 Uiso 0.428(9) 1 calc PR B 4 H21F H 0.4824 0.1751 -0.3999 0.050 Uiso 0.428(9) 1 calc PR B 4 C22B C 0.5998(10) 0.1835(11) -0.3527(6) 0.022(3) Uani 0.428(9) 1 d P B 4 N22B N 0.6579(7) 0.0678(12) -0.3645(4) 0.0226(19) Uani 0.428(9) 1 d P B 4 C24B C 0.7377(7) 0.1294(10) -0.3633(7) 0.024(2) Uani 0.428(9) 1 d P B 4 H24B H 0.7895 0.0739 -0.3694 0.029 Uiso 0.428(9) 1 calc PR B 4 C25B C 0.7299(8) 0.2858(13) -0.3516(7) 0.027(3) Uani 0.428(9) 1 d P B 4 H25B H 0.7749 0.3588 -0.3474 0.033 Uiso 0.428(9) 1 calc PR B 4 C23 C 0.6094(3) 0.4697(4) -0.3309(2) 0.0495(10) Uani 1 1 d . . . H23A H 0.6509 0.5096 -0.3667 0.074 Uiso 1 1 calc R B 3 H23B H 0.6316 0.4831 -0.2807 0.074 Uiso 1 1 calc R B 3 H23C H 0.5559 0.5270 -0.3360 0.074 Uiso 1 1 calc R B 3 C26 C 0.6393(2) -0.0961(3) -0.37428(19) 0.0450(8) Uani 1 1 d . . . H26A H 0.6101 -0.1703 -0.3411 0.067 Uiso 1 1 calc R B 3 H26B H 0.7010 -0.0997 -0.3634 0.067 Uiso 1 1 calc R B 3 C27 C 0.6238(4) -0.1402(4) -0.4540(2) 0.0634(10) Uani 1 1 d . B . H27A H 0.5635 -0.1253 -0.4659 0.095 Uiso 1 1 calc R . . H27B H 0.6392 -0.2493 -0.4615 0.095 Uiso 1 1 calc R . . H27C H 0.6586 -0.0746 -0.4863 0.095 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 S1 0.0367(4) 0.0334(3) 0.0318(3) 0.0059(3) 0.0007(5) -0.0017(4) O11 0.0819(16) 0.0322(11) 0.0748(15) 0.0143(11) 0.000(2) 0.0013(16) O12 0.0587(17) 0.0746(19) 0.0627(18) 0.0068(16) -0.0275(15) -0.0195(15) O13 0.0576(16) 0.0720(19) 0.0561(17) -0.0016(15) 0.0233(14) 0.0148(15) F11 0.1152(18) 0.0602(13) 0.0759(15) 0.0380(11) -0.0065(19) -0.0136(17) F12 0.0902(18) 0.108(2) 0.0504(15) -0.0036(13) -0.0312(15) -0.0097(16) F13 0.0803(17) 0.147(3) 0.0638(18) 0.0087(17) 0.0408(16) 0.0236(18) C1 0.0499(19) 0.058(2) 0.0374(16) 0.0033(15) 0.005(2) -0.005(2) S2 0.0355(4) 0.0328(3) 0.0309(3) 0.0024(3) 0.0009(5) -0.0029(4) O21 0.0556(16) 0.077(2) 0.0529(18) 0.0110(15) 0.0016(14) -0.0272(16) O22 0.0800(16) 0.0424(12) 0.0573(14) -0.0156(10) -0.0081(18) -0.0002(16) O23 0.0519(15) 0.0670(19) 0.0620(19) -0.0011(15) -0.0119(14) 0.0241(15) F21 0.0844(17) 0.110(2) 0.0603(15) 0.0200(15) -0.0264(14) 0.0242(16) F22 0.103(2) 0.162(3) 0.0627(18) 0.048(2) 0.0158(16) -0.046(2) F23 0.143(2) 0.0988(18) 0.0478(13) -0.0349(12) -0.0073(19) 0.022(2) C2 0.060(2) 0.062(2) 0.0389(17) 0.0021(15) 0.001(2) -0.003(2) N11A 0.053(6) 0.042(5) 0.032(3) 0.008(3) 0.010(3) -0.008(4) C11A 0.033(4) 0.034(7) 0.050(5) 0.014(8) 0.007(3) 0.004(6) C12A 0.043(6) 0.054(9) 0.029(4) 0.004(4) 0.002(4) 0.000(6) N12A 0.050(5) 0.031(4) 0.035(3) 0.003(3) -0.007(3) 0.001(3) C14A 0.044(4) 0.048(6) 0.049(5) 0.010(5) 0.001(4) -0.008(5) C15A 0.028(5) 0.043(6) 0.045(4) 0.010(5) 0.003(3) 0.012(4) N11B 0.026(5) 0.023(5) 0.026(4) -0.008(3) 0.015(4) -0.015(4) C11B 0.024(5) 0.017(7) 0.034(5) 0.007(6) 0.000(4) -0.007(6) C12B 0.033(6) 0.000(6) 0.021(4) -0.002(3) 0.005(4) 0.001(5) N12B 0.011(4) 0.025(5) 0.046(5) -0.006(4) -0.006(4) 0.000(4) C14B 0.021(5) 0.013(6) 0.037(5) 0.010(5) 0.005(4) 0.003(5) C15B 0.029(4) 0.023(5) 0.018(4) -0.001(4) -0.004(3) 0.006(5) C13 0.058(3) 0.0287(16) 0.0526(19) -0.0022(13) 0.0008(19) -0.0031(16) C16 0.0384(18) 0.0276(15) 0.066(2) 0.0019(14) -0.0013(19) -0.0074(16) C17 0.088(3) 0.0466(19) 0.077(3) -0.0265(18) 0.000(3) -0.002(3) N21A 0.056(6) 0.032(5) 0.032(4) 0.000(3) 0.002(4) -0.005(4) C21A 0.039(5) 0.057(10) 0.049(5) -0.008(9) -0.003(4) 0.003(8) C22A 0.045(7) 0.058(12) 0.026(5) 0.005(4) -0.002(4) 0.010(6) N22A 0.059(6) 0.033(5) 0.045(4) -0.002(3) -0.021(4) 0.006(4) C24A 0.041(4) 0.039(5) 0.044(4) -0.001(4) 0.012(3) -0.001(3) C25A 0.039(4) 0.036(5) 0.039(4) -0.003(4) 0.000(3) 0.018(4) N21B 0.022(5) 0.019(5) 0.027(4) 0.005(3) 0.004(3) -0.001(3) C21B 0.034(4) 0.026(5) 0.039(5) -0.004(5) 0.002(3) 0.009(4) C22B 0.031(6) 0.012(8) 0.022(5) 0.001(3) 0.003(4) 0.003(4) N22B 0.019(4) 0.028(5) 0.020(3) 0.012(3) -0.012(4) 0.003(4) C24B 0.020(4) 0.015(5) 0.038(5) 0.000(5) 0.013(3) 0.003(4) C25B 0.033(5) 0.021(6) 0.026(5) 0.005(4) 0.014(3) 0.008(4) C23 0.062(3) 0.0320(17) 0.054(2) 0.0002(14) -0.010(2) 0.0042(18) C26 0.053(2) 0.0252(15) 0.0567(19) 0.0011(13) 0.0032(19) 0.0014(16) C27 0.080(2) 0.0446(18) 0.065(2) -0.0131(16) 0.016(3) -0.005(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 S1 O13 1.418(3) . ? S1 O12 1.424(3) . ? S1 O11 1.436(2) . ? S1 C1 1.797(3) . ? F11 C1 1.330(4) . ? F12 C1 1.325(5) . ? F13 C1 1.317(5) . ? S2 O21 1.415(3) . ? S2 O23 1.429(3) . ? S2 O22 1.436(2) . ? S2 C2 1.805(3) . ? F21 C2 1.330(5) . ? F22 C2 1.297(5) . ? F23 C2 1.332(4) . ? N11A C12A 1.338(15) . ? N11A C15A 1.391(15) . ? N11A C13 1.490(10) . ? C11A C12A 1.456(16) . ? C11A H11A 0.9800 . ? C11A H11B 0.9800 . ? C11A H11C 0.9800 . ? C12A N12A 1.302(14) . ? N12A C14A 1.408(14) . ? N12A C16 1.426(7) . ? C14A C15A 1.293(13) . ? C14A H14A 0.9500 . ? C15A H15A 0.9500 . ? N11B C12B 1.358(16) . ? N11B C15B 1.379(16) . ? C11B C12B 1.506(19) . ? C11B H11D 0.9800 . ? C11B H11E 0.9800 . ? C11B H11F 0.9800 . ? C12B N12B 1.319(16) . ? N12B C14B 1.401(19) . ? N12B C16 1.497(12) . ? C14B C15B 1.369(16) . ? C14B H14B 0.9500 . ? C15B H15B 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C16 C17 1.493(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N21A C22A 1.326(16) . ? N21A C25A 1.415(15) . ? N21A C23 1.447(9) . ? C21A C22A 1.453(19) . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A H21C 0.9800 . ? C22A N22A 1.305(16) . ? N22A C24A 1.381(15) . ? N22A C26 1.482(10) . ? C24A C25A 1.298(13) . ? C24A H24A 0.9500 . ? C25A H25A 0.9500 . ? N21B C22B 1.343(16) . ? N21B C25B 1.387(18) . ? C21B C22B 1.49(2) . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 0.9800 . ? C22B N22B 1.369(16) . ? N22B C24B 1.363(16) . ? N22B C26 1.452(11) . ? C24B C25B 1.369(14) . ? C24B H24B 0.9500 . ? C25B H25B 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C26 C27 1.510(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 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 O13 S1 O12 116.83(16) . . ? O13 S1 O11 114.2(2) . . ? O12 S1 O11 114.0(2) . . ? O13 S1 C1 103.0(2) . . ? O12 S1 C1 103.2(2) . . ? O11 S1 C1 103.04(14) . . ? F13 C1 F12 107.1(3) . . ? F13 C1 F11 106.6(3) . . ? F12 C1 F11 106.9(4) . . ? F13 C1 S1 112.1(3) . . ? F12 C1 S1 112.2(3) . . ? F11 C1 S1 111.6(2) . . ? O21 S2 O23 116.71(15) . . ? O21 S2 O22 114.1(2) . . ? O23 S2 O22 113.13(19) . . ? O21 S2 C2 104.0(2) . . ? O23 S2 C2 103.6(2) . . ? O22 S2 C2 103.10(15) . . ? F22 C2 F21 107.9(3) . . ? F22 C2 F23 107.8(4) . . ? F21 C2 F23 105.7(4) . . ? F22 C2 S2 112.2(3) . . ? F21 C2 S2 112.4(3) . . ? F23 C2 S2 110.6(2) . . ? C12A N11A C15A 107.8(11) . . ? C12A N11A C13 129.8(11) . . ? C15A N11A C13 122.4(7) . . ? N12A C12A N11A 108.3(15) . . ? N12A C12A C11A 127.4(13) . . ? N11A C12A C11A 124.3(11) . . ? C12A N12A C14A 108.5(10) . . ? C12A N12A C16 127.5(12) . . ? C14A N12A C16 123.6(7) . . ? C15A C14A N12A 107.2(9) . . ? C15A C14A H14A 126.4 . . ? N12A C14A H14A 126.4 . . ? C14A C15A N11A 108.1(9) . . ? C14A C15A H15A 126.0 . . ? N11A C15A H15A 126.0 . . ? C12B N11B C15B 108.6(13) . . ? C12B C11B H11D 109.5 . . ? C12B C11B H11E 109.5 . . ? H11D C11B H11E 109.5 . . ? C12B C11B H11F 109.5 . . ? H11D C11B H11F 109.5 . . ? H11E C11B H11F 109.5 . . ? N12B C12B N11B 108.0(16) . . ? N12B C12B C11B 127.0(11) . . ? N11B C12B C11B 125.0(13) . . ? C12B N12B C14B 109.9(13) . . ? C12B N12B C16 127.1(11) . . ? C14B N12B C16 123.0(8) . . ? C15B C14B N12B 105.7(12) . . ? C15B C14B H14B 127.2 . . ? N12B C14B H14B 127.2 . . ? C14B C15B N11B 107.6(11) . . ? C14B C15B H15B 126.2 . . ? N11B C15B H15B 126.2 . . ? N12A C16 C17 114.4(4) . . ? N12A C16 N12B 31.9(3) . . ? C17 C16 N12B 108.2(5) . . ? C17 C16 H16A 108.7 . . ? N12B C16 H16A 135.9 . . ? C17 C16 H16B 108.7 . . ? N12B C16 H16B 82.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C22A N21A C25A 108.4(12) . . ? C22A N21A C23 130.1(14) . . ? C25A N21A C23 121.5(7) . . ? N22A C22A N21A 108.1(18) . . ? N22A C22A C21A 126.9(13) . . ? N21A C22A C21A 125.0(14) . . ? C22A N22A C24A 108.8(12) . . ? C22A N22A C26 128.3(13) . . ? C24A N22A C26 122.8(7) . . ? C25A C24A N22A 108.9(8) . . ? C25A C24A H24A 125.5 . . ? N22A C24A H24A 125.5 . . ? C24A C25A N21A 105.7(7) . . ? C24A C25A H25A 127.1 . . ? N21A C25A H25A 127.1 . . ? C22B N21B C25B 109.2(14) . . ? N22B C22B N21B 107.1(18) . . ? N22B C22B C21B 126.5(12) . . ? N21B C22B C21B 126.3(14) . . ? C22B N22B C24B 109.2(12) . . ? C22B N22B C26 126.3(12) . . ? C24B N22B C26 124.5(7) . . ? C25B C24B N22B 107.6(11) . . ? C25B C24B H24B 126.2 . . ? N22B C24B H24B 126.2 . . ? C24B C25B N21B 106.8(12) . . ? C24B C25B H25B 126.6 . . ? N21B C25B H25B 126.6 . . ? N22B C26 N22A 32.1(3) . . ? N22B C26 C27 113.1(4) . . ? N22A C26 C27 108.9(4) . . ? C27 C26 H26A 109.9 . . ? C27 C26 H26B 109.9 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? _refine_diff_density_max 0.265 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.043 #===END data_3 _database_code_CSD 169679 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-butyl-3-methylimidazolium tetraphenylborate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H15 N2, B1 C24 H20' _chemical_formula_sum 'C32 H35 B N2' _chemical_formula_weight 458.45 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' 'B' 'B' 0.0013 0.0007 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 8.834(1) _cell_length_b 17.007(1) _cell_length_c 17.875(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2685.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2638 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.35 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.129 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type none _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 'Nonius Kappa CCD' _diffrn_measurement_method '\f and \w scans to fill Ewald sphere' _diffrn_reflns_number 10172 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 25.37 _reflns_number_total 4703 _reflns_number_gt 4123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III for Windows (Farrugia,1997)' _computing_publication_material 'WINGX (Farrugia, 1999)' _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^)+(0.0384P)^2^+0.1867P] 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 SHELXL _refine_ls_extinction_coef 0.0155(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 4703 _refine_ls_number_parameters 355 _refine_ls_number_restraints 32 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0772 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.048 _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 C1 C 0.58140(19) 0.96561(9) 0.90401(9) 0.0306(4) Uani 1 1 d . . . H1 H 0.5083 0.9706 0.9412 0.037 Uiso 1 1 calc R . . C2 C 0.7213(2) 0.98846(10) 0.80507(9) 0.0358(4) Uani 1 1 d . . . H2 H 0.7605 1.0124 0.7625 0.043 Uiso 1 1 calc R . . C3 C 0.7690(2) 0.92055(10) 0.83610(9) 0.0359(4) Uani 1 1 d . . . H3 H 0.8470 0.8887 0.8188 0.043 Uiso 1 1 calc R . . C4 C 0.6925(3) 0.84010(9) 0.94848(10) 0.0480(5) Uani 1 1 d . . . H4A H 0.6366 0.7966 0.9282 0.072 Uiso 1 1 calc R . . H4B H 0.6516 0.8540 0.9964 0.072 Uiso 1 1 calc R . . H4C H 0.7969 0.8255 0.9540 0.072 Uiso 1 1 calc R . . C5 C 0.5242(2) 1.09118(10) 0.83824(11) 0.0380(4) Uani 1 1 d D . . C6A C 0.5645(4) 1.14836(15) 0.9000(2) 0.0375(9) Uani 0.818(8) 1 d P A 1 H6A1 H 0.5293 1.1271 0.9472 0.045 Uiso 0.818(8) 1 calc PR A 1 H6A2 H 0.5108 1.1973 0.8913 0.045 Uiso 0.818(8) 1 calc PR A 1 C7A C 0.7328(4) 1.16618(16) 0.9066(2) 0.0433(9) Uani 0.818(8) 1 d P A 1 H7A1 H 0.7859 1.1197 0.9238 0.052 Uiso 0.818(8) 1 calc PR A 1 H7A2 H 0.7728 1.1804 0.8580 0.052 Uiso 0.818(8) 1 calc PR A 1 C8A C 0.7584(12) 1.2332(5) 0.9613(5) 0.085(2) Uani 0.818(8) 1 d P A 1 H8A1 H 0.7128 1.2204 1.0086 0.128 Uiso 0.818(8) 1 calc PR A 1 H8A2 H 0.7135 1.2804 0.9420 0.128 Uiso 0.818(8) 1 calc PR A 1 H8A3 H 0.8651 1.2411 0.9681 0.128 Uiso 0.818(8) 1 calc PR A 1 C6B C 0.6194(17) 1.1622(6) 0.8587(11) 0.047(4) Uani 0.182(8) 1 d PU A 2 H6B1 H 0.7097 1.1621 0.8279 0.056 Uiso 0.182(8) 1 calc PR A 2 H6B2 H 0.5626 1.2093 0.8466 0.056 Uiso 0.182(8) 1 calc PR A 2 C7B C 0.667(2) 1.1667(9) 0.9403(12) 0.063(5) Uani 0.182(8) 1 d PU A 2 H7B1 H 0.7073 1.1153 0.9529 0.075 Uiso 0.182(8) 1 calc PR A 2 H7B2 H 0.5746 1.1728 0.9690 0.075 Uiso 0.182(8) 1 calc PR A 2 C8B C 0.780(5) 1.227(2) 0.972(2) 0.092(13) Uani 0.182(8) 1 d PU A 2 H8B1 H 0.8458 1.2447 0.9329 0.138 Uiso 0.182(8) 1 calc PR A 2 H8B2 H 0.8384 1.2030 1.0110 0.138 Uiso 0.182(8) 1 calc PR A 2 H8B3 H 0.7251 1.2711 0.9921 0.138 Uiso 0.182(8) 1 calc PR A 2 C11 C 0.84374(17) 1.46673(8) 0.81315(8) 0.0222(3) Uani 1 1 d . . . C12 C 0.93604(18) 1.40255(9) 0.79533(8) 0.0259(4) Uani 1 1 d . . . H12 H 1.0396 1.4063 0.8041 0.031 Uiso 1 1 calc R . . C13 C 0.8785(2) 1.33327(9) 0.76496(9) 0.0324(4) Uani 1 1 d . . . H13 H 0.9437 1.2921 0.7533 0.039 Uiso 1 1 calc R . . C14 C 0.7255(2) 1.32541(9) 0.75218(9) 0.0356(4) Uani 1 1 d . . . H14 H 0.6864 1.2787 0.7332 0.043 Uiso 1 1 calc R . . C15 C 0.63116(19) 1.38795(9) 0.76806(10) 0.0342(4) Uani 1 1 d . . . H15 H 0.5277 1.3836 0.7593 0.041 Uiso 1 1 calc R . . C16 C 0.68933(18) 1.45669(9) 0.79682(9) 0.0284(4) Uani 1 1 d . . . H16 H 0.6235 1.4983 0.8058 0.034 Uiso 1 1 calc R . . C21 C 0.83980(17) 1.62047(8) 0.79577(8) 0.0218(3) Uani 1 1 d . . . C22 C 0.90069(19) 1.62676(9) 0.72359(8) 0.0281(4) Uani 1 1 d . . . H22 H 0.9729 1.5902 0.7087 0.034 Uiso 1 1 calc R . . C23 C 0.85860(19) 1.68489(9) 0.67327(9) 0.0335(4) Uani 1 1 d . . . H23 H 0.9033 1.6871 0.6262 0.040 Uiso 1 1 calc R . . C24 C 0.74991(19) 1.73950(9) 0.69337(9) 0.0348(4) Uani 1 1 d . . . H24 H 0.7227 1.7796 0.6606 0.042 Uiso 1 1 calc R . . C25 C 0.6826(2) 1.73368(9) 0.76255(9) 0.0328(4) Uani 1 1 d . . . H25 H 0.6071 1.7690 0.7761 0.039 Uiso 1 1 calc R . . C26 C 0.72684(17) 1.67539(8) 0.81228(9) 0.0269(4) Uani 1 1 d . . . H26 H 0.6793 1.6727 0.8586 0.032 Uiso 1 1 calc R . . C31 C 0.81996(16) 1.55577(9) 0.93611(8) 0.0225(3) Uani 1 1 d . . . C32 C 0.8207(2) 1.62635(9) 0.97722(9) 0.0294(4) Uani 1 1 d . . . H32 H 0.8643 1.6708 0.9558 0.035 Uiso 1 1 calc R . . C33 C 0.7590(2) 1.63235(11) 1.04824(9) 0.0401(4) Uani 1 1 d . . . H33 H 0.7603 1.6805 1.0729 0.048 Uiso 1 1 calc R . . C34 C 0.6958(2) 1.56783(11) 1.08268(9) 0.0438(5) Uani 1 1 d . . . H34 H 0.6544 1.5718 1.1304 0.053 Uiso 1 1 calc R . . C35 C 0.6954(2) 1.49729(10) 1.04484(9) 0.0366(4) Uani 1 1 d . . . H35 H 0.6540 1.4530 1.0674 0.044 Uiso 1 1 calc R . . C36 C 0.75594(19) 1.49156(9) 0.97353(8) 0.0283(4) Uani 1 1 d . . . H36 H 0.7539 1.4430 0.9495 0.034 Uiso 1 1 calc R . . C41 C 1.08027(17) 1.55621(8) 0.86744(8) 0.0221(3) Uani 1 1 d . . . C42 C 1.15683(18) 1.49749(9) 0.90779(9) 0.0275(4) Uani 1 1 d . . . H42 H 1.1029 1.4534 0.9232 0.033 Uiso 1 1 calc R . . C43 C 1.30954(19) 1.50237(9) 0.92569(9) 0.0332(4) Uani 1 1 d . . . H43 H 1.3557 1.4616 0.9518 0.040 Uiso 1 1 calc R . . C44 C 1.39338(19) 1.56764(10) 0.90489(9) 0.0336(4) Uani 1 1 d . . . H44 H 1.4957 1.5712 0.9167 0.040 Uiso 1 1 calc R . . C45 C 1.32148(19) 1.62719(9) 0.86629(9) 0.0307(4) Uani 1 1 d . . . H45 H 1.3757 1.6718 0.8525 0.037 Uiso 1 1 calc R . . C46 C 1.16898(17) 1.62130(9) 0.84779(8) 0.0247(3) Uani 1 1 d . . . H46 H 1.1241 1.6622 0.8213 0.030 Uiso 1 1 calc R . . B B 0.89679(19) 1.54975(9) 0.85233(9) 0.0212(4) Uani 1 1 d . . . N1 N 0.60410(15) 1.01538(7) 0.84814(7) 0.0293(3) Uani 1 1 d . A . N2 N 0.68089(16) 0.90741(7) 0.89783(7) 0.0310(3) Uani 1 1 d . . . H51 H 0.4133(3) 1.0829(9) 0.8383(9) 0.037 Uiso 1 1 d D . . H52 H 0.5466(19) 1.1100(9) 0.7870(4) 0.037 Uiso 1 1 d 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 0.0320(9) 0.0307(9) 0.0292(9) -0.0002(7) 0.0057(7) -0.0007(8) C2 0.0366(10) 0.0386(10) 0.0322(9) 0.0028(8) 0.0094(8) -0.0044(8) C3 0.0335(10) 0.0384(10) 0.0357(9) -0.0061(8) 0.0073(8) 0.0003(8) C4 0.0751(15) 0.0332(10) 0.0359(10) 0.0063(8) 0.0053(10) 0.0123(10) C5 0.0357(10) 0.0367(10) 0.0417(11) 0.0060(9) -0.0063(9) 0.0035(8) C6A 0.0440(18) 0.0308(14) 0.0379(18) 0.0051(11) -0.0036(15) 0.0087(12) C7A 0.047(2) 0.0393(13) 0.0430(17) -0.0062(13) -0.0044(15) -0.0020(13) C8A 0.080(4) 0.095(5) 0.080(4) -0.033(3) -0.017(3) -0.026(4) C6B 0.047(7) 0.032(6) 0.062(11) 0.021(6) -0.005(7) -0.001(5) C7B 0.059(11) 0.070(9) 0.059(11) 0.004(8) -0.007(9) 0.043(8) C8B 0.09(2) 0.053(14) 0.13(3) -0.074(15) -0.027(17) 0.037(14) C11 0.0258(8) 0.0228(8) 0.0178(7) 0.0018(6) 0.0010(6) 0.0007(6) C12 0.0252(8) 0.0264(8) 0.0262(8) -0.0004(7) -0.0004(7) 0.0019(7) C13 0.0394(10) 0.0217(9) 0.0362(10) -0.0042(7) -0.0037(8) 0.0069(7) C14 0.0425(11) 0.0234(8) 0.0409(10) -0.0041(8) -0.0089(8) -0.0050(8) C15 0.0268(9) 0.0331(10) 0.0428(10) -0.0047(8) -0.0071(8) -0.0039(7) C16 0.0273(9) 0.0244(8) 0.0337(9) -0.0039(7) -0.0023(7) 0.0039(7) C21 0.0217(8) 0.0196(7) 0.0240(8) -0.0031(6) -0.0047(6) -0.0038(6) C22 0.0294(9) 0.0283(8) 0.0266(9) -0.0007(7) -0.0029(7) -0.0004(7) C23 0.0372(10) 0.0372(10) 0.0262(9) 0.0051(7) -0.0051(7) -0.0103(8) C24 0.0395(10) 0.0268(9) 0.0381(10) 0.0100(8) -0.0169(9) -0.0061(8) C25 0.0306(9) 0.0241(8) 0.0437(10) 0.0007(8) -0.0117(8) 0.0041(7) C26 0.0281(9) 0.0230(8) 0.0295(8) -0.0001(7) -0.0041(7) -0.0007(7) C31 0.0177(8) 0.0266(8) 0.0232(8) 0.0019(7) -0.0036(6) 0.0039(7) C32 0.0335(9) 0.0286(8) 0.0262(8) -0.0015(7) -0.0031(7) 0.0035(8) C33 0.0485(12) 0.0424(10) 0.0294(10) -0.0100(8) -0.0032(9) 0.0107(9) C34 0.0442(12) 0.0639(13) 0.0233(9) -0.0002(9) 0.0070(8) 0.0067(10) C35 0.0335(10) 0.0470(11) 0.0291(9) 0.0071(8) 0.0015(8) -0.0044(9) C36 0.0258(8) 0.0316(9) 0.0275(8) 0.0024(7) -0.0019(7) -0.0014(7) C41 0.0239(8) 0.0237(8) 0.0186(7) -0.0029(6) 0.0011(6) 0.0020(7) C42 0.0274(9) 0.0271(9) 0.0281(9) 0.0027(7) -0.0013(7) -0.0006(7) C43 0.0294(9) 0.0329(10) 0.0374(9) 0.0044(7) -0.0066(8) 0.0074(8) C44 0.0211(8) 0.0417(10) 0.0380(10) 0.0004(8) -0.0039(8) 0.0023(8) C45 0.0270(9) 0.0313(9) 0.0336(9) 0.0009(7) 0.0012(7) -0.0059(7) C46 0.0251(8) 0.0253(8) 0.0237(8) 0.0015(6) -0.0016(7) 0.0013(7) B 0.0214(9) 0.0203(9) 0.0218(9) -0.0006(7) -0.0005(7) 0.0003(7) N1 0.0303(8) 0.0290(7) 0.0287(7) 0.0025(6) -0.0005(6) -0.0018(6) N2 0.0380(8) 0.0286(7) 0.0264(7) 0.0001(6) 0.0039(6) 0.0021(6) _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 1.324(2) . ? C1 N2 1.328(2) . ? C1 H1 0.9300 . ? C2 C3 1.349(2) . ? C2 N1 1.369(2) . ? C2 H2 0.9300 . ? C3 N2 1.369(2) . ? C3 H3 0.9300 . ? C4 N2 1.4631(19) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 N1 1.481(2) . ? C5 C6A 1.513(3) . ? C5 C6B 1.517(12) . ? C5 H51 0.990(3) . ? C5 H52 0.990(2) . ? C6A C7A 1.522(6) . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C7A C8A 1.518(8) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8A H8A1 0.9600 . ? C8A H8A2 0.9600 . ? C8A H8A3 0.9600 . ? C6B C7B 1.52(3) . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C7B C8B 1.54(5) . ? C7B H7B1 0.9700 . ? C7B H7B2 0.9700 . ? C8B H8B1 0.9600 . ? C8B H8B2 0.9600 . ? C8B H8B3 0.9600 . ? C11 C12 1.399(2) . ? C11 C16 1.405(2) . ? C11 B 1.644(2) . ? C12 C13 1.393(2) . ? C12 H12 0.9300 . ? C13 C14 1.377(2) . ? C13 H13 0.9300 . ? C14 C15 1.381(2) . ? C14 H14 0.9300 . ? C15 C16 1.377(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C26 1.398(2) . ? C21 C22 1.402(2) . ? C21 B 1.650(2) . ? C22 C23 1.387(2) . ? C22 H22 0.9300 . ? C23 C24 1.383(2) . ? C23 H23 0.9300 . ? C24 C25 1.376(2) . ? C24 H24 0.9300 . ? C25 C26 1.388(2) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C36 1.400(2) . ? C31 C32 1.407(2) . ? C31 B 1.647(2) . ? C32 C33 1.385(2) . ? C32 H32 0.9300 . ? C33 C34 1.376(2) . ? C33 H33 0.9300 . ? C34 C35 1.377(2) . ? C34 H34 0.9300 . ? C35 C36 1.386(2) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C41 C46 1.401(2) . ? C41 C42 1.405(2) . ? C41 B 1.647(2) . ? C42 C43 1.389(2) . ? C42 H42 0.9300 . ? C43 C44 1.385(2) . ? C43 H43 0.9300 . ? C44 C45 1.380(2) . ? C44 H44 0.9300 . ? C45 C46 1.391(2) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? 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 N1 C1 N2 108.26(14) . . ? N1 C1 H1 125.9 . . ? N2 C1 H1 125.9 . . ? C3 C2 N1 106.93(15) . . ? C3 C2 H2 126.5 . . ? N1 C2 H2 126.5 . . ? C2 C3 N2 107.08(15) . . ? C2 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C5 C6A 111.12(15) . . ? N1 C5 C6B 113.6(5) . . ? C6A C5 C6B 35.1(7) . . ? N1 C5 H51 110.4(9) . . ? C6A C5 H51 108.9(10) . . ? C6B C5 H51 131.4(11) . . ? N1 C5 H52 107.3(10) . . ? C6A C5 H52 114.7(10) . . ? C6B C5 H52 81.6(12) . . ? H51 C5 H52 104.2(14) . . ? C5 C6A C7A 114.5(3) . . ? C5 C6A H6A1 108.6 . . ? C7A C6A H6A1 108.6 . . ? C5 C6A H6A2 108.6 . . ? C7A C6A H6A2 108.6 . . ? H6A1 C6A H6A2 107.6 . . ? C8A C7A C6A 110.2(5) . . ? C8A C7A H7A1 109.6 . . ? C6A C7A H7A1 109.6 . . ? C8A C7A H7A2 109.6 . . ? C6A C7A H7A2 109.6 . . ? H7A1 C7A H7A2 108.1 . . ? C7B C6B C5 115.2(16) . . ? C7B C6B H6B1 108.5 . . ? C5 C6B H6B1 108.5 . . ? C7B C6B H6B2 108.5 . . ? C5 C6B H6B2 108.5 . . ? H6B1 C6B H6B2 107.5 . . ? C6B C7B C8B 125(3) . . ? C6B C7B H7B1 106.2 . . ? C8B C7B H7B1 106.2 . . ? C6B C7B H7B2 106.2 . . ? C8B C7B H7B2 106.2 . . ? H7B1 C7B H7B2 106.4 . . ? C7B C8B H8B1 109.5 . . ? C7B C8B H8B2 109.5 . . ? H8B1 C8B H8B2 109.5 . . ? C7B C8B H8B3 109.5 . . ? H8B1 C8B H8B3 109.5 . . ? H8B2 C8B H8B3 109.5 . . ? C12 C11 C16 115.06(14) . . ? C12 C11 B 126.93(13) . . ? C16 C11 B 118.00(13) . . ? C13 C12 C11 122.39(15) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C14 C13 C12 120.32(15) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 118.92(15) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 120.36(15) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 122.90(14) . . ? C15 C16 H16 118.6 . . ? C11 C16 H16 118.6 . . ? C26 C21 C22 114.65(14) . . ? C26 C21 B 125.13(13) . . ? C22 C21 B 120.16(13) . . ? C23 C22 C21 123.24(15) . . ? C23 C22 H22 118.4 . . ? C21 C22 H22 118.4 . . ? C24 C23 C22 119.74(16) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 119.02(15) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 120.37(15) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 122.88(15) . . ? C25 C26 H26 118.6 . . ? C21 C26 H26 118.6 . . ? C36 C31 C32 114.68(13) . . ? C36 C31 B 123.52(13) . . ? C32 C31 B 121.72(13) . . ? C33 C32 C31 122.65(16) . . ? C33 C32 H32 118.7 . . ? C31 C32 H32 118.7 . . ? C34 C33 C32 120.71(16) . . ? C34 C33 H33 119.6 . . ? C32 C33 H33 119.6 . . ? C33 C34 C35 118.42(15) . . ? C33 C34 H34 120.8 . . ? C35 C34 H34 120.8 . . ? C34 C35 C36 120.80(16) . . ? C34 C35 H35 119.6 . . ? C36 C35 H35 119.6 . . ? C35 C36 C31 122.72(15) . . ? C35 C36 H36 118.6 . . ? C31 C36 H36 118.6 . . ? C46 C41 C42 114.89(14) . . ? C46 C41 B 124.20(13) . . ? C42 C41 B 120.69(13) . . ? C43 C42 C41 122.91(15) . . ? C43 C42 H42 118.5 . . ? C41 C42 H42 118.5 . . ? C44 C43 C42 120.35(15) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C45 C44 C43 118.43(16) . . ? C45 C44 H44 120.8 . . ? C43 C44 H44 120.8 . . ? C44 C45 C46 120.78(16) . . ? C44 C45 H45 119.6 . . ? C46 C45 H45 119.6 . . ? C45 C46 C41 122.63(15) . . ? C45 C46 H46 118.7 . . ? C41 C46 H46 118.7 . . ? C11 B C41 114.05(12) . . ? C11 B C31 108.85(12) . . ? C41 B C31 104.61(11) . . ? C11 B C21 106.15(12) . . ? C41 B C21 110.62(12) . . ? C31 B C21 112.71(12) . . ? C1 N1 C2 108.96(14) . . ? C1 N1 C5 125.05(14) . . ? C2 N1 C5 125.78(14) . . ? C1 N2 C3 108.76(13) . . ? C1 N2 C4 125.31(14) . . ? C3 N2 C4 125.92(14) . . ? _refine_diff_density_max 0.182 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.030 #===END data_4 _database_code_CSD 169680 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (3-butylimidazole)triphenylboron ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C25 H27 B N2)' _chemical_formula_sum 'C50 H54 B2 N4' _chemical_formula_weight 732.62 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' 'B' 'B' 0.0013 0.0007 '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' _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 11.3171(10) _cell_length_b 12.7981(10) _cell_length_c 15.6049(10) _cell_angle_alpha 73.70(1) _cell_angle_beta 74.38(1) _cell_angle_gamma 77.22(1) _cell_volume 2063.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1616 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.61 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.179 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa CCD' _diffrn_measurement_method '\f and \w scans to fill Ewald sphere' _diffrn_reflns_number 11327 _diffrn_reflns_av_R_equivalents 0.0156 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 27.52 _reflns_number_total 9087 _reflns_number_gt 6746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III for Windows (Farrugia,1997)' _computing_publication_material 'WINGX (Farrugia, 1999)' _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 w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+0.9451P] 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 9087 _refine_ls_number_parameters 534 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1324 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.036 _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 B1 B 0.47144(15) 0.91142(13) 0.25968(11) 0.0191(3) Uani 1 1 d . . . N11 N 0.55776(11) 0.87097(10) 0.17061(8) 0.0189(3) Uani 1 1 d . . . N12 N 0.66922(11) 0.77244(10) 0.07424(8) 0.0212(3) Uani 1 1 d . . . C111 C 0.33895(13) 0.96825(12) 0.23089(9) 0.0194(3) Uani 1 1 d . . . C112 C 0.27624(14) 0.90888(13) 0.19855(10) 0.0237(3) Uani 1 1 d . . . H112 H 0.3144 0.8372 0.1907 0.028 Uiso 1 1 calc R . . C113 C 0.16065(15) 0.95125(14) 0.17765(11) 0.0284(4) Uani 1 1 d . . . H113 H 0.1205 0.9083 0.1569 0.034 Uiso 1 1 calc R . . C114 C 0.10382(15) 1.05663(15) 0.18711(11) 0.0297(4) Uani 1 1 d . . . H114 H 0.0245 1.0860 0.1734 0.036 Uiso 1 1 calc R . . C115 C 0.16404(15) 1.11809(14) 0.21662(11) 0.0295(4) Uani 1 1 d . . . H115 H 0.1267 1.1907 0.2222 0.035 Uiso 1 1 calc R . . C116 C 0.27929(14) 1.07400(13) 0.23817(10) 0.0242(3) Uani 1 1 d . . . H116 H 0.3188 1.1177 0.2586 0.029 Uiso 1 1 calc R . . C121 C 0.53952(13) 0.99538(12) 0.28454(10) 0.0196(3) Uani 1 1 d . . . C122 C 0.65220(15) 1.03085(13) 0.23469(11) 0.0265(3) Uani 1 1 d . . . H122 H 0.6943 1.0051 0.1812 0.032 Uiso 1 1 calc R . . C123 C 0.70476(16) 1.10267(14) 0.26084(12) 0.0315(4) Uani 1 1 d . . . H123 H 0.7809 1.1255 0.2248 0.038 Uiso 1 1 calc R . . C124 C 0.64684(16) 1.14076(13) 0.33861(12) 0.0303(4) Uani 1 1 d . . . H124 H 0.6820 1.1904 0.3560 0.036 Uiso 1 1 calc R . . C125 C 0.53663(16) 1.10563(13) 0.39093(11) 0.0277(4) Uani 1 1 d . . . H125 H 0.4963 1.1303 0.4452 0.033 Uiso 1 1 calc R . . C126 C 0.48512(15) 1.03438(13) 0.36409(10) 0.0241(3) Uani 1 1 d . . . H126 H 0.4097 1.0110 0.4012 0.029 Uiso 1 1 calc R . . C131 C 0.45630(14) 0.80505(12) 0.34634(10) 0.0193(3) Uani 1 1 d . . . C132 C 0.56021(15) 0.74157(13) 0.37899(10) 0.0254(3) Uani 1 1 d . . . H132 H 0.6405 0.7580 0.3467 0.030 Uiso 1 1 calc R . . C133 C 0.54994(16) 0.65584(14) 0.45655(11) 0.0301(4) Uani 1 1 d . . . H133 H 0.6225 0.6141 0.4761 0.036 Uiso 1 1 calc R . . C134 C 0.43417(16) 0.63083(13) 0.50562(11) 0.0297(4) Uani 1 1 d . . . H134 H 0.4266 0.5725 0.5592 0.036 Uiso 1 1 calc R . . C135 C 0.33020(16) 0.69154(14) 0.47586(11) 0.0323(4) Uani 1 1 d . . . H135 H 0.2502 0.6752 0.5091 0.039 Uiso 1 1 calc R . . C136 C 0.34161(15) 0.77695(13) 0.39720(11) 0.0272(3) Uani 1 1 d . . . H136 H 0.2686 0.8174 0.3776 0.033 Uiso 1 1 calc R . . C11 C 0.60963(13) 0.76995(12) 0.16117(10) 0.0198(3) Uani 1 1 d . . . H11 H 0.6051 0.7052 0.2093 0.024 Uiso 1 1 calc R . . C12 C 0.58492(14) 0.94041(12) 0.08481(10) 0.0224(3) Uani 1 1 d . . . H12 H 0.5592 1.0180 0.0703 0.027 Uiso 1 1 calc R . . C13 C 0.65401(14) 0.88006(12) 0.02495(10) 0.0230(3) Uani 1 1 d . . . H13 H 0.6858 0.9067 -0.0386 0.028 Uiso 1 1 calc R . . C14 C 0.73381(15) 0.67606(13) 0.03684(11) 0.0263(3) Uani 1 1 d D . . H14A H 0.7767 0.6220 0.0823 0.032 Uiso 1 1 calc R . . H14B H 0.7976 0.6998 -0.0189 0.032 Uiso 1 1 calc R . . C15 C 0.64503(16) 0.62100(14) 0.01325(12) 0.0321(4) Uani 1 1 d D . . H15A H 0.6925 0.5554 -0.0092 0.038 Uiso 1 1 calc R . . H15B H 0.5835 0.5951 0.0698 0.038 Uiso 1 1 calc R . . C16 C 0.57613(18) 0.69465(15) -0.05823(13) 0.0366(4) Uani 1 1 d D . . H16A H 0.6374 0.7244 -0.1135 0.044 Uiso 1 1 calc R . . H16B H 0.5241 0.7578 -0.0342 0.044 Uiso 1 1 calc R . . C17 C 0.49397(17) 0.63601(15) -0.08524(13) 0.0370(4) Uani 1 1 d D . . H17A H 0.4525 0.6878 -0.1317 0.055 Uiso 1 1 calc R . . H17B H 0.4314 0.6081 -0.0312 0.055 Uiso 1 1 calc R . . H17C H 0.5450 0.5742 -0.1103 0.055 Uiso 1 1 calc R . . B2 B 1.03294(16) 0.58680(14) 0.23619(11) 0.0197(3) Uani 1 1 d . . . N21 N 0.95487(11) 0.63754(10) 0.32257(8) 0.0208(3) Uani 1 1 d . . . N22 N 0.86132(13) 0.74756(11) 0.41371(9) 0.0277(3) Uani 1 1 d . B . C211 C 1.15991(13) 0.51756(12) 0.26754(9) 0.0196(3) Uani 1 1 d . . . C212 C 1.20211(14) 0.40610(12) 0.26964(10) 0.0225(3) Uani 1 1 d . . . H212 H 1.1541 0.3662 0.2527 0.027 Uiso 1 1 calc R . . C213 C 1.31253(15) 0.35116(13) 0.29582(11) 0.0265(3) Uani 1 1 d . . . H213 H 1.3382 0.2751 0.2965 0.032 Uiso 1 1 calc R . . C214 C 1.38469(15) 0.40684(14) 0.32082(11) 0.0270(3) Uani 1 1 d . . . H214 H 1.4604 0.3698 0.3379 0.032 Uiso 1 1 calc R . . C215 C 1.34517(15) 0.51732(14) 0.32061(11) 0.0286(4) Uani 1 1 d . . . H215 H 1.3936 0.5564 0.3381 0.034 Uiso 1 1 calc R . . C216 C 1.23493(15) 0.57093(13) 0.29489(11) 0.0259(3) Uani 1 1 d . . . H216 H 1.2090 0.6466 0.2958 0.031 Uiso 1 1 calc R . . C221 C 1.05971(14) 0.68808(12) 0.14628(10) 0.0194(3) Uani 1 1 d . . . C222 C 0.96051(14) 0.76318(12) 0.11499(10) 0.0232(3) Uani 1 1 d . . . H222 H 0.8781 0.7559 0.1487 0.028 Uiso 1 1 calc R . . C223 C 0.97851(15) 0.84751(13) 0.03668(11) 0.0270(3) Uani 1 1 d . . . H223 H 0.9092 0.8974 0.0182 0.032 Uiso 1 1 calc R . . C224 C 1.09721(16) 0.85890(13) -0.01449(11) 0.0283(4) Uani 1 1 d . . . H224 H 1.1101 0.9169 -0.0679 0.034 Uiso 1 1 calc R . . C225 C 1.19701(16) 0.78522(14) 0.01265(11) 0.0292(4) Uani 1 1 d . . . H225 H 1.2788 0.7916 -0.0229 0.035 Uiso 1 1 calc R . . C226 C 1.17811(15) 0.70139(13) 0.09219(10) 0.0250(3) Uani 1 1 d . . . H226 H 1.2480 0.6519 0.1101 0.030 Uiso 1 1 calc R . . C231 C 0.94848(14) 0.51222(12) 0.21560(10) 0.0205(3) Uani 1 1 d . . . C232 C 0.82746(15) 0.49693(14) 0.26350(11) 0.0281(4) Uani 1 1 d . . . H232 H 0.7903 0.5296 0.3140 0.034 Uiso 1 1 calc R . . C233 C 0.75960(17) 0.43507(16) 0.23932(12) 0.0368(4) Uani 1 1 d . . . H233 H 0.6776 0.4265 0.2735 0.044 Uiso 1 1 calc R . . C234 C 0.81040(17) 0.38637(14) 0.16638(12) 0.0337(4) Uani 1 1 d . . . H234 H 0.7644 0.3437 0.1504 0.040 Uiso 1 1 calc R . . C235 C 0.92941(16) 0.40062(13) 0.11685(12) 0.0304(4) Uani 1 1 d . . . H235 H 0.9657 0.3677 0.0663 0.037 Uiso 1 1 calc R . . C236 C 0.99579(15) 0.46279(13) 0.14086(11) 0.0254(3) Uani 1 1 d . . . H236 H 1.0768 0.4724 0.1052 0.031 Uiso 1 1 calc R . . C21 C 0.91721(15) 0.74159(13) 0.32771(11) 0.0246(3) Uani 1 1 d . . . H21 H 0.9284 0.8034 0.2773 0.030 Uiso 1 1 calc R . . C22 C 0.92239(15) 0.57436(13) 0.41036(10) 0.0262(3) Uani 1 1 d . . . H22 H 0.9384 0.4962 0.4282 0.031 Uiso 1 1 calc R . . C23 C 0.86422(15) 0.64196(14) 0.46674(11) 0.0282(4) Uani 1 1 d . . . H23 H 0.8316 0.6205 0.5308 0.034 Uiso 1 1 calc R . . C24 C 0.80941(19) 0.84959(15) 0.44605(13) 0.0401(5) Uani 1 1 d D . . H24A H 0.7193 0.8512 0.4724 0.048 Uiso 1 1 calc R A 1 H24B H 0.8204 0.9142 0.3936 0.048 Uiso 1 1 calc R A 1 C25A C 0.8748(3) 0.8569(3) 0.5199(2) 0.0431(9) Uani 0.625(4) 1 d PD B 1 H25A H 0.8412 0.9292 0.5355 0.052 Uiso 0.625(4) 1 calc PR B 1 H25B H 0.8494 0.7996 0.5757 0.052 Uiso 0.625(4) 1 calc PR B 1 C26A C 1.0136(7) 0.8448(9) 0.4988(6) 0.059(2) Uani 0.625(4) 1 d PD B 1 H26A H 1.0404 0.9076 0.4484 0.071 Uiso 0.625(4) 1 calc PR B 1 H26B H 1.0493 0.7764 0.4772 0.071 Uiso 0.625(4) 1 calc PR B 1 C27A C 1.0650(3) 0.8407(3) 0.5803(2) 0.0496(10) Uani 0.625(4) 1 d PD B 1 H27A H 1.1556 0.8353 0.5617 0.074 Uiso 0.625(4) 1 calc PR B 1 H27B H 1.0429 0.7763 0.6293 0.074 Uiso 0.625(4) 1 calc PR B 1 H27C H 1.0296 0.9079 0.6025 0.074 Uiso 0.625(4) 1 calc PR B 1 C25B C 0.8927(4) 0.9221(4) 0.4292(4) 0.0385(14) Uani 0.375(4) 1 d PD B 2 H25C H 0.8510 0.9856 0.4565 0.046 Uiso 0.375(4) 1 calc PR B 2 H85D H 0.9206 0.9505 0.3624 0.046 Uiso 0.375(4) 1 calc PR B 2 C26B C 1.0029(12) 0.8647(12) 0.4696(9) 0.060(4) Uani 0.375(4) 1 d PD B 2 H26C H 1.0457 0.8037 0.4395 0.072 Uiso 0.375(4) 1 calc PR B 2 H26D H 1.0616 0.9174 0.4551 0.072 Uiso 0.375(4) 1 calc PR B 2 C27B C 0.9743(5) 0.8194(5) 0.5691(4) 0.0490(17) Uani 0.375(4) 1 d PD B 2 H27D H 0.9248 0.8773 0.5996 0.073 Uiso 0.375(4) 1 calc PR B 2 H27E H 1.0518 0.7921 0.5904 0.073 Uiso 0.375(4) 1 calc PR B 2 H27F H 0.9271 0.7587 0.5836 0.073 Uiso 0.375(4) 1 calc PR B 2 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 B1 0.0183(8) 0.0208(8) 0.0174(8) -0.0045(6) -0.0024(6) -0.0032(6) N11 0.0187(6) 0.0203(6) 0.0176(6) -0.0041(5) -0.0043(5) -0.0032(5) N12 0.0199(6) 0.0243(6) 0.0205(6) -0.0085(5) -0.0049(5) -0.0008(5) C111 0.0198(7) 0.0222(7) 0.0153(7) -0.0040(6) -0.0025(6) -0.0037(6) C112 0.0249(8) 0.0238(8) 0.0240(8) -0.0067(6) -0.0058(6) -0.0052(6) C113 0.0260(8) 0.0387(9) 0.0239(8) -0.0073(7) -0.0060(7) -0.0116(7) C114 0.0196(8) 0.0454(10) 0.0220(8) -0.0076(7) -0.0053(6) -0.0003(7) C115 0.0284(9) 0.0309(9) 0.0279(9) -0.0120(7) -0.0069(7) 0.0054(7) C116 0.0261(8) 0.0248(8) 0.0232(8) -0.0088(6) -0.0061(6) -0.0022(6) C121 0.0193(7) 0.0210(7) 0.0189(7) -0.0031(6) -0.0069(6) -0.0027(6) C122 0.0249(8) 0.0309(8) 0.0255(8) -0.0088(7) -0.0023(6) -0.0090(7) C123 0.0272(9) 0.0359(9) 0.0343(9) -0.0076(7) -0.0036(7) -0.0154(7) C124 0.0355(9) 0.0270(8) 0.0352(9) -0.0079(7) -0.0154(8) -0.0088(7) C125 0.0320(9) 0.0291(8) 0.0257(8) -0.0112(7) -0.0099(7) -0.0017(7) C126 0.0231(8) 0.0279(8) 0.0219(8) -0.0063(6) -0.0045(6) -0.0054(6) C131 0.0220(7) 0.0194(7) 0.0178(7) -0.0069(6) -0.0035(6) -0.0037(6) C132 0.0223(8) 0.0312(8) 0.0216(8) -0.0035(6) -0.0048(6) -0.0055(6) C133 0.0319(9) 0.0325(9) 0.0243(8) -0.0011(7) -0.0114(7) -0.0028(7) C134 0.0414(10) 0.0269(8) 0.0194(8) 0.0004(6) -0.0073(7) -0.0095(7) C135 0.0298(9) 0.0374(9) 0.0250(9) -0.0012(7) 0.0005(7) -0.0121(7) C136 0.0229(8) 0.0305(8) 0.0249(8) -0.0020(7) -0.0044(6) -0.0047(7) C11 0.0204(7) 0.0205(7) 0.0193(7) -0.0049(6) -0.0059(6) -0.0025(6) C12 0.0256(8) 0.0214(7) 0.0192(7) -0.0033(6) -0.0052(6) -0.0037(6) C13 0.0233(8) 0.0273(8) 0.0172(7) -0.0034(6) -0.0038(6) -0.0046(6) C14 0.0244(8) 0.0279(8) 0.0280(8) -0.0140(7) -0.0066(7) 0.0037(6) C15 0.0341(9) 0.0294(9) 0.0354(10) -0.0153(7) -0.0066(8) -0.0020(7) C16 0.0413(10) 0.0344(9) 0.0385(10) -0.0072(8) -0.0137(8) -0.0104(8) C17 0.0368(10) 0.0413(10) 0.0385(10) -0.0114(8) -0.0110(8) -0.0120(8) B2 0.0214(8) 0.0201(8) 0.0177(8) -0.0059(6) -0.0027(6) -0.0035(6) N21 0.0214(6) 0.0226(6) 0.0189(6) -0.0056(5) -0.0049(5) -0.0032(5) N22 0.0274(7) 0.0304(7) 0.0256(7) -0.0137(6) -0.0038(6) 0.0014(6) C211 0.0211(7) 0.0215(7) 0.0155(7) -0.0042(6) -0.0022(6) -0.0042(6) C212 0.0262(8) 0.0232(8) 0.0199(7) -0.0073(6) -0.0051(6) -0.0045(6) C213 0.0293(8) 0.0231(8) 0.0258(8) -0.0091(6) -0.0059(7) 0.0029(6) C214 0.0230(8) 0.0346(9) 0.0224(8) -0.0074(7) -0.0070(6) 0.0010(7) C215 0.0278(8) 0.0330(9) 0.0300(9) -0.0086(7) -0.0109(7) -0.0076(7) C216 0.0280(8) 0.0226(8) 0.0299(9) -0.0076(6) -0.0092(7) -0.0043(6) C221 0.0223(7) 0.0204(7) 0.0178(7) -0.0070(6) -0.0046(6) -0.0047(6) C222 0.0219(8) 0.0267(8) 0.0228(8) -0.0058(6) -0.0067(6) -0.0051(6) C223 0.0295(8) 0.0270(8) 0.0262(8) -0.0036(6) -0.0125(7) -0.0033(7) C224 0.0383(9) 0.0265(8) 0.0200(8) -0.0012(6) -0.0070(7) -0.0093(7) C225 0.0271(8) 0.0328(9) 0.0240(8) -0.0051(7) 0.0020(7) -0.0085(7) C226 0.0236(8) 0.0253(8) 0.0237(8) -0.0052(6) -0.0030(6) -0.0024(6) C231 0.0220(7) 0.0193(7) 0.0200(7) -0.0023(6) -0.0068(6) -0.0030(6) C232 0.0264(8) 0.0345(9) 0.0239(8) -0.0068(7) -0.0021(7) -0.0103(7) C233 0.0315(9) 0.0477(11) 0.0338(10) -0.0043(8) -0.0040(8) -0.0222(8) C234 0.0416(10) 0.0306(9) 0.0369(10) -0.0048(7) -0.0167(8) -0.0161(8) C235 0.0366(9) 0.0273(8) 0.0334(9) -0.0126(7) -0.0144(8) -0.0019(7) C236 0.0240(8) 0.0279(8) 0.0264(8) -0.0093(6) -0.0062(6) -0.0037(6) C21 0.0267(8) 0.0237(8) 0.0228(8) -0.0078(6) -0.0053(6) -0.0002(6) C22 0.0301(8) 0.0284(8) 0.0190(8) -0.0031(6) -0.0058(6) -0.0055(7) C23 0.0271(8) 0.0369(9) 0.0198(8) -0.0073(7) -0.0029(6) -0.0059(7) C24 0.0448(11) 0.0366(10) 0.0375(10) -0.0223(8) -0.0062(8) 0.0101(8) C25A 0.0369(17) 0.0451(18) 0.056(2) -0.0324(16) -0.0093(15) 0.0007(14) C26A 0.026(2) 0.068(4) 0.095(6) -0.050(4) -0.011(3) 0.005(2) C27A 0.0383(19) 0.065(2) 0.059(2) -0.0370(18) -0.0154(16) -0.0012(16) C25B 0.027(2) 0.041(3) 0.052(3) -0.029(2) 0.005(2) -0.008(2) C26B 0.057(7) 0.059(7) 0.084(8) -0.048(6) 0.002(5) -0.028(6) C27B 0.034(3) 0.067(4) 0.026(3) 0.001(3) 0.008(2) -0.001(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 B1 N11 1.613(2) . ? B1 C131 1.630(2) . ? B1 C121 1.631(2) . ? B1 C111 1.636(2) . ? N11 C11 1.3275(19) . ? N11 C12 1.3814(19) . ? N12 C11 1.3374(19) . ? N12 C13 1.3748(19) . ? N12 C14 1.4737(19) . ? C111 C116 1.393(2) . ? C111 C112 1.408(2) . ? C112 C113 1.389(2) . ? C112 H112 0.9500 . ? C113 C114 1.390(2) . ? C113 H113 0.9500 . ? C114 C115 1.380(2) . ? C114 H114 0.9500 . ? C115 C116 1.392(2) . ? C115 H115 0.9500 . ? C116 H116 0.9500 . ? C121 C122 1.400(2) . ? C121 C126 1.403(2) . ? C122 C123 1.396(2) . ? C122 H122 0.9500 . ? C123 C124 1.379(2) . ? C123 H123 0.9500 . ? C124 C125 1.385(2) . ? C124 H124 0.9500 . ? C125 C126 1.388(2) . ? C125 H125 0.9500 . ? C126 H126 0.9500 . ? C131 C136 1.391(2) . ? C131 C132 1.404(2) . ? C132 C133 1.385(2) . ? C132 H132 0.9500 . ? C133 C134 1.383(2) . ? C133 H133 0.9500 . ? C134 C135 1.375(2) . ? C134 H134 0.9500 . ? C135 C136 1.394(2) . ? C135 H135 0.9500 . ? C136 H136 0.9500 . ? C11 H11 0.9500 . ? C12 C13 1.351(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.516(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.514(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.517(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? B2 N21 1.617(2) . ? B2 C211 1.631(2) . ? B2 C221 1.632(2) . ? B2 C231 1.634(2) . ? N21 C21 1.3235(19) . ? N21 C22 1.3799(19) . ? N22 C21 1.336(2) . ? N22 C23 1.371(2) . ? N22 C24 1.475(2) . ? C211 C212 1.394(2) . ? C211 C216 1.409(2) . ? C212 C213 1.396(2) . ? C212 H212 0.9500 . ? C213 C214 1.383(2) . ? C213 H213 0.9500 . ? C214 C215 1.385(2) . ? C214 H214 0.9500 . ? C215 C216 1.387(2) . ? C215 H215 0.9500 . ? C216 H216 0.9500 . ? C221 C226 1.396(2) . ? C221 C222 1.406(2) . ? C222 C223 1.386(2) . ? C222 H222 0.9500 . ? C223 C224 1.381(2) . ? C223 H223 0.9500 . ? C224 C225 1.381(2) . ? C224 H224 0.9500 . ? C225 C226 1.396(2) . ? C225 H225 0.9500 . ? C226 H226 0.9500 . ? C231 C232 1.399(2) . ? C231 C236 1.405(2) . ? C232 C233 1.397(2) . ? C232 H232 0.9500 . ? C233 C234 1.379(3) . ? C233 H233 0.9500 . ? C234 C235 1.383(2) . ? C234 H234 0.9500 . ? C235 C236 1.386(2) . ? C235 H235 0.9500 . ? C236 H236 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.349(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25B 1.392(5) . ? C24 C25A 1.561(4) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25A C26A 1.497(7) . ? C25A H25A 0.9900 . ? C25A H25B 0.9900 . ? C26A C27A 1.518(8) . ? C26A H26A 0.9900 . ? C26A H26B 0.9900 . ? C27A H27A 0.9800 . ? C27A H27B 0.9800 . ? C27A H27C 0.9800 . ? C25B C26B 1.500(11) . ? C25B H25C 0.9900 . ? C25B H85D 0.9900 . ? C26B C27B 1.469(12) . ? C26B H26C 0.9900 . ? C26B H26D 0.9900 . ? C27B H27D 0.9800 . ? C27B H27E 0.9800 . ? C27B H27F 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 N11 B1 C131 109.15(11) . . ? N11 B1 C121 109.09(12) . . ? C131 B1 C121 107.98(12) . . ? N11 B1 C111 104.56(11) . . ? C131 B1 C111 111.90(12) . . ? C121 B1 C111 114.03(12) . . ? C11 N11 C12 106.42(12) . . ? C11 N11 B1 129.71(12) . . ? C12 N11 B1 123.76(12) . . ? C11 N12 C13 107.97(12) . . ? C11 N12 C14 125.98(13) . . ? C13 N12 C14 125.97(13) . . ? C116 C111 C112 115.72(13) . . ? C116 C111 B1 124.06(13) . . ? C112 C111 B1 120.20(13) . . ? C113 C112 C111 122.44(15) . . ? C113 C112 H112 118.8 . . ? C111 C112 H112 118.8 . . ? C112 C113 C114 119.85(15) . . ? C112 C113 H113 120.1 . . ? C114 C113 H113 120.1 . . ? C115 C114 C113 119.22(15) . . ? C115 C114 H114 120.4 . . ? C113 C114 H114 120.4 . . ? C114 C115 C116 120.22(15) . . ? C114 C115 H115 119.9 . . ? C116 C115 H115 119.9 . . ? C115 C116 C111 122.54(15) . . ? C115 C116 H116 118.7 . . ? C111 C116 H116 118.7 . . ? C122 C121 C126 115.33(14) . . ? C122 C121 B1 125.79(13) . . ? C126 C121 B1 118.84(13) . . ? C123 C122 C121 122.29(15) . . ? C123 C122 H122 118.9 . . ? C121 C122 H122 118.9 . . ? C124 C123 C122 120.44(16) . . ? C124 C123 H123 119.8 . . ? C122 C123 H123 119.8 . . ? C123 C124 C125 119.03(15) . . ? C123 C124 H124 120.5 . . ? C125 C124 H124 120.5 . . ? C124 C125 C126 119.98(15) . . ? C124 C125 H125 120.0 . . ? C126 C125 H125 120.0 . . ? C125 C126 C121 122.89(15) . . ? C125 C126 H126 118.6 . . ? C121 C126 H126 118.6 . . ? C136 C131 C132 115.78(14) . . ? C136 C131 B1 123.17(13) . . ? C132 C131 B1 120.81(13) . . ? C133 C132 C131 122.39(15) . . ? C133 C132 H132 118.8 . . ? C131 C132 H132 118.8 . . ? C134 C133 C132 120.11(15) . . ? C134 C133 H133 119.9 . . ? C132 C133 H133 119.9 . . ? C135 C134 C133 119.11(15) . . ? C135 C134 H134 120.4 . . ? C133 C134 H134 120.4 . . ? C134 C135 C136 120.33(16) . . ? C134 C135 H135 119.8 . . ? C136 C135 H135 119.8 . . ? C131 C136 C135 122.27(15) . . ? C131 C136 H136 118.9 . . ? C135 C136 H136 118.9 . . ? N11 C11 N12 110.29(13) . . ? N11 C11 H11 124.9 . . ? N12 C11 H11 124.9 . . ? C13 C12 N11 108.88(13) . . ? C13 C12 H12 125.6 . . ? N11 C12 H12 125.6 . . ? C12 C13 N12 106.43(13) . . ? C12 C13 H13 126.8 . . ? N12 C13 H13 126.8 . . ? N12 C14 C15 112.03(13) . . ? N12 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? N12 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 114.28(14) . . ? C16 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 113.45(15) . . ? C15 C16 H16A 108.9 . . ? C17 C16 H16A 108.9 . . ? C15 C16 H16B 108.9 . . ? C17 C16 H16B 108.9 . . ? H16A C16 H16B 107.7 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N21 B2 C211 104.20(11) . . ? N21 B2 C221 108.75(12) . . ? C211 B2 C221 112.60(12) . . ? N21 B2 C231 108.75(12) . . ? C211 B2 C231 114.43(12) . . ? C221 B2 C231 107.91(12) . . ? C21 N21 C22 106.33(13) . . ? C21 N21 B2 129.89(13) . . ? C22 N21 B2 123.63(12) . . ? C21 N22 C23 107.66(13) . . ? C21 N22 C24 126.06(14) . . ? C23 N22 C24 126.26(14) . . ? C212 C211 C216 115.73(13) . . ? C212 C211 B2 124.57(13) . . ? C216 C211 B2 119.70(13) . . ? C211 C212 C213 122.23(14) . . ? C211 C212 H212 118.9 . . ? C213 C212 H212 118.9 . . ? C214 C213 C212 120.34(14) . . ? C214 C213 H213 119.8 . . ? C212 C213 H213 119.8 . . ? C213 C214 C215 119.14(14) . . ? C213 C214 H214 120.4 . . ? C215 C214 H214 120.4 . . ? C214 C215 C216 120.01(15) . . ? C214 C215 H215 120.0 . . ? C216 C215 H215 120.0 . . ? C215 C216 C211 122.54(14) . . ? C215 C216 H216 118.7 . . ? C211 C216 H216 118.7 . . ? C226 C221 C222 115.92(13) . . ? C226 C221 B2 123.49(13) . . ? C222 C221 B2 120.41(13) . . ? C223 C222 C221 122.44(14) . . ? C223 C222 H222 118.8 . . ? C221 C222 H222 118.8 . . ? C224 C223 C222 119.97(15) . . ? C224 C223 H223 120.0 . . ? C222 C223 H223 120.0 . . ? C225 C224 C223 119.42(15) . . ? C225 C224 H224 120.3 . . ? C223 C224 H224 120.3 . . ? C224 C225 C226 120.20(15) . . ? C224 C225 H225 119.9 . . ? C226 C225 H225 119.9 . . ? C221 C226 C225 122.02(15) . . ? C221 C226 H226 119.0 . . ? C225 C226 H226 119.0 . . ? C232 C231 C236 115.41(14) . . ? C232 C231 B2 125.57(13) . . ? C236 C231 B2 118.93(13) . . ? C233 C232 C231 122.04(15) . . ? C233 C232 H232 119.0 . . ? C231 C232 H232 119.0 . . ? C234 C233 C232 120.67(16) . . ? C234 C233 H233 119.7 . . ? C232 C233 H233 119.7 . . ? C233 C234 C235 118.91(16) . . ? C233 C234 H234 120.5 . . ? C235 C234 H234 120.5 . . ? C234 C235 C236 120.08(16) . . ? C234 C235 H235 120.0 . . ? C236 C235 H235 120.0 . . ? C235 C236 C231 122.89(15) . . ? C235 C236 H236 118.6 . . ? C231 C236 H236 118.6 . . ? N21 C21 N22 110.55(14) . . ? N21 C21 H21 124.7 . . ? N22 C21 H21 124.7 . . ? C23 C22 N21 108.75(14) . . ? C23 C22 H22 125.6 . . ? N21 C22 H22 125.6 . . ? C22 C23 N22 106.70(14) . . ? C22 C23 H23 126.7 . . ? N22 C23 H23 126.7 . . ? C25B C24 N22 115.5(2) . . ? C25B C24 C25A 56.8(3) . . ? N22 C24 C25A 111.00(17) . . ? C25B C24 H24A 135.0 . . ? N22 C24 H24A 109.4 . . ? C25A C24 H24A 109.4 . . ? C25B C24 H24B 54.2 . . ? N22 C24 H24B 109.4 . . ? C25A C24 H24B 109.4 . . ? H24A C24 H24B 108.0 . . ? C26A C25A C24 119.1(4) . . ? C26A C25A H25A 107.5 . . ? C24 C25A H25A 107.5 . . ? C26A C25A H25B 107.5 . . ? C24 C25A H25B 107.5 . . ? H25A C25A H25B 107.0 . . ? C25A C26A C27A 113.3(5) . . ? C25A C26A H26A 108.9 . . ? C27A C26A H26A 108.9 . . ? C25A C26A H26B 108.9 . . ? C27A C26A H26B 108.9 . . ? H26A C26A H26B 107.7 . . ? C26A C27A H27A 109.5 . . ? C26A C27A H27B 109.5 . . ? H27A C27A H27B 109.5 . . ? C26A C27A H27C 109.5 . . ? H27A C27A H27C 109.5 . . ? H27B C27A H27C 109.5 . . ? C24 C25B C26B 110.2(7) . . ? C24 C25B H25C 109.6 . . ? C26B C25B H25C 109.6 . . ? C24 C25B H85D 109.6 . . ? C26B C25B H85D 109.6 . . ? H25C C25B H85D 108.1 . . ? C27B C26B C25B 115.1(10) . . ? C27B C26B H26C 108.5 . . ? C25B C26B H26C 108.5 . . ? C27B C26B H26D 108.5 . . ? C25B C26B H26D 108.5 . . ? H26C C26B H26D 107.5 . . ? C26B C27B H27D 109.5 . . ? C26B C27B H27E 109.5 . . ? H27D C27B H27E 109.5 . . ? C26B C27B H27F 109.5 . . ? H27D C27B H27F 109.5 . . ? H27E C27B H27F 109.5 . . ? _refine_diff_density_max 0.406 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.046 #===END