# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Pamela Dean' 'Craig Forsyth' 'Douglas MacFarlane' 'Jennifer Pringle' 'Janet Scott' _publ_contact_author_name 'Pamela Dean' _publ_contact_author_email PAMELA.DEAN@SCI.MONASH.EDU.AU _publ_section_title ; Interactions in Bisamide Ionic Liquids - Insights from a Hirshfeld Analysis of their Crystalline States ; # Attachment 'B809606F_Global.cif' data_emimmes2 _database_code_depnum_ccdc_archive 'CCDC 701482' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-ethyl-1-methylimidazolium bis(methanesulfonyl)amide ; _chemical_name_common '[C2mim][NMes2]' _chemical_melting_point ? _chemical_formula_moiety 'C6 H11 N2, C2 H6 N O4 S2' _chemical_formula_sum 'C8 H17 N3 O4 S2' _chemical_formula_weight 283.37 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' 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 P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.2135(2) _cell_length_b 13.7443(4) _cell_length_c 7.8355(2) _cell_angle_alpha 90.00 _cell_angle_beta 106.172(2) _cell_angle_gamma 90.00 _cell_volume 642.67(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 6102 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 26.37 _exptl_crystal_description anhedral _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.464 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 0.422 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8839 _exptl_absorpt_correction_T_max 0.9204 _exptl_absorpt_process_details 'sadabs (Bruker AXS, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9724 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2931 _reflns_number_gt 2863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_data_reduction 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _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^)+(0.0337P)^2^+0.0820P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(5) _refine_ls_number_reflns 2931 _refine_ls_number_parameters 158 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0256 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0614 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.098 _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 N1 N 0.0935(2) 0.92014(9) 0.86882(18) 0.0159(3) Uani 1 1 d . . . C1 C 0.1794(3) 0.95465(12) 1.0325(2) 0.0200(3) Uani 1 1 d . . . H1 H 0.3270 0.9431 1.1058 0.024 Uiso 1 1 calc R . . N2 N 0.0255(3) 1.00751(10) 1.07607(19) 0.0247(3) Uani 1 1 d . . . C2 C -0.1233(3) 0.95273(12) 0.8055(2) 0.0201(3) Uani 1 1 d . . . H2 H -0.2235 0.9396 0.6921 0.024 Uiso 1 1 calc R . . C3 C -0.1666(3) 1.00745(13) 0.9366(2) 0.0252(4) Uani 1 1 d . . . H3 H -0.3033 1.0395 0.9327 0.030 Uiso 1 1 calc R . . C4 C 0.0600(5) 1.05749(17) 1.2480(3) 0.0423(6) Uani 1 1 d . . . H4B H 0.0244 1.1274 1.2260 0.051 Uiso 1 1 calc R . . H4A H 0.2200 1.0523 1.3156 0.051 Uiso 1 1 calc R . . C5 C -0.0788(4) 1.01732(15) 1.3567(3) 0.0340(4) Uani 1 1 d . . . H5B H -0.2377 1.0262 1.2941 0.051 Uiso 1 1 calc R . . H5C H -0.0441 1.0514 1.4711 0.051 Uiso 1 1 calc R . . H5A H -0.0467 0.9478 1.3772 0.051 Uiso 1 1 calc R . . C6 C 0.2189(3) 0.86464(13) 0.7695(2) 0.0235(4) Uani 1 1 d . . . H6B H 0.2863 0.9094 0.7016 0.035 Uiso 1 1 calc R . . H6C H 0.1174 0.8200 0.6878 0.035 Uiso 1 1 calc R . . H6A H 0.3374 0.8273 0.8524 0.035 Uiso 1 1 calc R . . S1A S 0.64806(6) 0.68670(3) 0.12377(5) 0.01589(9) Uani 1 1 d . . . O1A O 0.7152(2) 0.60359(8) 0.23911(16) 0.0253(3) Uani 1 1 d . . . N1A N 0.4938(2) 0.76154(10) 0.19132(17) 0.0177(3) Uani 1 1 d . . . C1A C 0.8925(3) 0.75154(13) 0.1217(3) 0.0244(4) Uani 1 1 d . . . H1AA H 0.9972 0.7078 0.0864 0.037 Uiso 1 1 calc R . . H1AB H 0.9633 0.7774 0.2407 0.037 Uiso 1 1 calc R . . H1AC H 0.8529 0.8054 0.0369 0.037 Uiso 1 1 calc R . . S2A S 0.54271(7) 0.78144(3) 0.39899(5) 0.01972(10) Uani 1 1 d . . . O2A O 0.5334(2) 0.66394(9) -0.05867(16) 0.0251(3) Uani 1 1 d . . . C2A C 0.4182(3) 0.68534(16) 0.4865(2) 0.0271(3) Uani 1 1 d . . . H2AA H 0.4451 0.6946 0.6147 0.041 Uiso 1 1 calc R . . H2AB H 0.4839 0.6234 0.4645 0.041 Uiso 1 1 calc R . . H2AC H 0.2566 0.6846 0.4289 0.041 Uiso 1 1 calc R . . O3A O 0.7784(2) 0.78028(11) 0.49303(15) 0.0287(3) Uani 1 1 d . . . O4A O 0.4239(2) 0.86959(9) 0.41686(18) 0.0325(3) 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 N1 0.0181(6) 0.0160(6) 0.0141(6) 0.0010(5) 0.0054(5) 0.0003(5) C1 0.0221(8) 0.0225(8) 0.0158(8) -0.0007(6) 0.0058(6) -0.0070(6) N2 0.0365(8) 0.0199(7) 0.0222(7) -0.0062(6) 0.0156(7) -0.0073(6) C2 0.0190(8) 0.0215(8) 0.0192(8) 0.0043(6) 0.0045(6) 0.0034(6) C3 0.0284(9) 0.0219(8) 0.0291(9) 0.0037(7) 0.0144(7) 0.0054(7) C4 0.0686(15) 0.0340(11) 0.0332(11) -0.0213(9) 0.0290(11) -0.0217(10) C5 0.0468(12) 0.0363(11) 0.0210(9) -0.0030(8) 0.0130(9) 0.0004(9) C6 0.0229(8) 0.0274(9) 0.0214(9) -0.0039(7) 0.0083(7) 0.0051(7) S1A 0.01805(17) 0.01499(16) 0.01463(18) -0.00023(15) 0.00456(13) -0.00031(14) O1A 0.0360(7) 0.0171(6) 0.0233(6) 0.0039(5) 0.0093(5) 0.0050(5) N1A 0.0178(6) 0.0212(7) 0.0141(7) 0.0015(5) 0.0049(5) 0.0028(5) C1A 0.0188(7) 0.0247(8) 0.0318(10) -0.0015(7) 0.0107(7) -0.0031(6) S2A 0.0232(2) 0.02203(19) 0.01401(18) -0.00160(15) 0.00535(15) 0.00071(15) O2A 0.0297(7) 0.0285(7) 0.0159(6) -0.0046(5) 0.0045(5) -0.0022(5) C2A 0.0313(9) 0.0338(9) 0.0178(8) 0.0062(8) 0.0095(7) -0.0018(8) O3A 0.0250(6) 0.0378(7) 0.0192(6) -0.0055(6) -0.0004(5) -0.0053(6) O4A 0.0478(8) 0.0295(7) 0.0252(7) -0.0015(6) 0.0184(6) 0.0098(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 N1 C1 1.332(2) . ? N1 C2 1.374(2) . ? N1 C6 1.461(2) . ? C1 N2 1.319(2) . ? C1 H1 0.9500 . ? N2 C3 1.376(2) . ? N2 C4 1.474(2) . ? C2 C3 1.359(2) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C5 1.478(3) . ? C4 H4B 0.9900 . ? C4 H4A 0.9900 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C5 H5A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C6 H6A 0.9800 . ? S1A O2A 1.4427(12) . ? S1A O1A 1.4442(12) . ? S1A N1A 1.5938(14) . ? S1A C1A 1.7651(17) . ? N1A S2A 1.5935(14) . ? C1A H1AA 0.9800 . ? C1A H1AB 0.9800 . ? C1A H1AC 0.9800 . ? S2A O3A 1.4447(13) . ? S2A O4A 1.4456(13) . ? S2A C2A 1.763(2) . ? C2A H2AA 0.9800 . ? C2A H2AB 0.9800 . ? C2A H2AC 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 C1 N1 C2 108.72(14) . . ? C1 N1 C6 124.70(15) . . ? C2 N1 C6 126.35(14) . . ? N2 C1 N1 108.69(15) . . ? N2 C1 H1 125.7 . . ? N1 C1 H1 125.7 . . ? C1 N2 C3 108.99(14) . . ? C1 N2 C4 124.19(18) . . ? C3 N2 C4 126.82(18) . . ? C3 C2 N1 106.74(15) . . ? C3 C2 H2 126.6 . . ? N1 C2 H2 126.6 . . ? C2 C3 N2 106.85(15) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? N2 C4 C5 113.17(17) . . ? N2 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? N2 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? H4B C4 H4A 107.8 . . ? C4 C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C5 H5A 109.5 . . ? H5B C5 H5A 109.5 . . ? H5C C5 H5A 109.5 . . ? N1 C6 H6B 109.5 . . ? N1 C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C6 H6A 109.5 . . ? H6B C6 H6A 109.5 . . ? H6C C6 H6A 109.5 . . ? O2A S1A O1A 115.17(8) . . ? O2A S1A N1A 107.00(7) . . ? O1A S1A N1A 113.48(7) . . ? O2A S1A C1A 106.81(8) . . ? O1A S1A C1A 107.80(8) . . ? N1A S1A C1A 106.02(8) . . ? S2A N1A S1A 119.24(8) . . ? S1A C1A H1AA 109.5 . . ? S1A C1A H1AB 109.5 . . ? H1AA C1A H1AB 109.5 . . ? S1A C1A H1AC 109.5 . . ? H1AA C1A H1AC 109.5 . . ? H1AB C1A H1AC 109.5 . . ? O3A S2A O4A 115.61(9) . . ? O3A S2A N1A 113.39(7) . . ? O4A S2A N1A 106.58(8) . . ? O3A S2A C2A 106.59(8) . . ? O4A S2A C2A 107.41(9) . . ? N1A S2A C2A 106.79(8) . . ? S2A C2A H2AA 109.5 . . ? S2A C2A H2AB 109.5 . . ? H2AA C2A H2AB 109.5 . . ? S2A C2A H2AC 109.5 . . ? H2AA C2A H2AC 109.5 . . ? H2AB C2A H2AC 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 N1 C1 N2 0.27(18) . . . . ? C6 N1 C1 N2 175.02(15) . . . . ? N1 C1 N2 C3 0.04(19) . . . . ? N1 C1 N2 C4 179.98(16) . . . . ? C1 N1 C2 C3 -0.47(18) . . . . ? C6 N1 C2 C3 -175.12(15) . . . . ? N1 C2 C3 N2 0.48(19) . . . . ? C1 N2 C3 C2 -0.33(19) . . . . ? C4 N2 C3 C2 179.73(17) . . . . ? C1 N2 C4 C5 -113.5(2) . . . . ? C3 N2 C4 C5 66.4(3) . . . . ? O2A S1A N1A S2A 165.34(9) . . . . ? O1A S1A N1A S2A 37.19(12) . . . . ? C1A S1A N1A S2A -80.93(11) . . . . ? S1A N1A S2A O3A 35.77(12) . . . . ? S1A N1A S2A O4A 164.09(9) . . . . ? S1A N1A S2A C2A -81.33(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.210 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.047 #============================================================================END data_P14nmes2 _database_code_depnum_ccdc_archive 'CCDC 701483' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-butyl-1-methyl pyrrolidinium bis(methanesulfonyl)amide ; _chemical_name_common '[C4mpyr][NMes2]' _chemical_melting_point 37 _chemical_formula_moiety 'C9 H20 N, C2 H6 N O4 S2' _chemical_formula_sum 'C11 H26 N2 O4 S2' _chemical_formula_weight 314.46 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 13.7961(7) _cell_length_b 10.955(6) _cell_length_c 20.8776(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3155.4(20) _cell_formula_units_Z 8 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 7952 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.43 _exptl_crystal_description cut _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.349 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9026 _exptl_absorpt_correction_T_max 0.9335 _exptl_absorpt_process_details 'sadabs (Bruker AXS, 2005)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX KAPPA CCD' _diffrn_measurement_method '0.5 deg frames in phi and omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 58574 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3621 _reflns_number_gt 3289 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_cell_refinement 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_data_reduction 'Bruker Apex II V 1.0 (Bruker ASX, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Pov-ray for windows, version 3.1' _computing_publication_material 'Microsoft Office' _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^)+(0.0431P)^2^+2.6370P] 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 3621 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0967 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _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 N1 N -0.04638(10) 0.44119(14) 0.12759(7) 0.0152(3) Uani 1 1 d . . . C1 C -0.00282(13) 0.35075(18) 0.08100(9) 0.0200(4) Uani 1 1 d . . . C2 C -0.04809(15) 0.22959(19) 0.09816(10) 0.0257(4) Uani 1 1 d . . . C3 C -0.14704(16) 0.2602(2) 0.12713(12) 0.0315(5) Uani 1 1 d . . . C4 C -0.15050(13) 0.39928(18) 0.13380(9) 0.0189(4) Uani 1 1 d . . . C5 C 0.00376(14) 0.43301(19) 0.19105(9) 0.0213(4) Uani 1 1 d . . . C6 C -0.03772(13) 0.56721(17) 0.09939(8) 0.0174(4) Uani 1 1 d . . . C7 C -0.06917(14) 0.67155(18) 0.14198(9) 0.0199(4) Uani 1 1 d . . . C8 C -0.06997(15) 0.78814(18) 0.10201(9) 0.0240(4) Uani 1 1 d . . . C9 C -0.08531(17) 0.90228(19) 0.14179(10) 0.0275(4) Uani 1 1 d . . . S1A S 0.26698(3) 0.61520(4) 0.19354(2) 0.01591(12) Uani 1 1 d . . . O1A O 0.37077(10) 0.59606(15) 0.19073(7) 0.0291(3) Uani 1 1 d . . . N1A N 0.21121(11) 0.56823(14) 0.13142(7) 0.0159(3) Uani 1 1 d . . . C1A C 0.24767(17) 0.77388(19) 0.19790(10) 0.0265(4) Uani 1 1 d . . . S2A S 0.25366(3) 0.59221(4) 0.061738(19) 0.01583(12) Uani 1 1 d . . . O2A O 0.21844(11) 0.56127(12) 0.24789(6) 0.0244(3) Uani 1 1 d . . . C2A C 0.34564(15) 0.4830(2) 0.04900(10) 0.0253(4) Uani 1 1 d . . . O3A O 0.17661(10) 0.56321(14) 0.01745(6) 0.0279(3) Uani 1 1 d . . . O4A O 0.29739(10) 0.71079(12) 0.05400(6) 0.0241(3) Uani 1 1 d . . . H1AA H 0.2767(18) 0.803(2) 0.2349(12) 0.037(7) Uiso 1 1 d . . . H2AA H 0.3921(18) 0.491(2) 0.0818(12) 0.038(7) Uiso 1 1 d . . . H1AB H 0.1794(19) 0.787(2) 0.1987(11) 0.036(7) Uiso 1 1 d . . . H2AB H 0.3694(17) 0.498(2) 0.0065(12) 0.031(6) Uiso 1 1 d . . . H1AC H 0.2728(17) 0.813(2) 0.1602(11) 0.030(6) Uiso 1 1 d . . . H2AC H 0.3196(18) 0.400(2) 0.0511(11) 0.029(6) Uiso 1 1 d . . . H1A H -0.0226(17) 0.378(2) 0.0388(11) 0.027(6) Uiso 1 1 d . . . H2A H -0.052(2) 0.181(3) 0.0599(13) 0.045(7) Uiso 1 1 d . . . H3A H -0.200(2) 0.235(3) 0.0974(14) 0.057(8) Uiso 1 1 d . . . H4A H -0.1837(16) 0.433(2) 0.0980(11) 0.022(5) Uiso 1 1 d . . . H5A H 0.0048(16) 0.352(2) 0.2028(11) 0.023(6) Uiso 1 1 d . . . H6A H -0.0744(17) 0.566(2) 0.0601(10) 0.025(6) Uiso 1 1 d . . . H7A H -0.1327(18) 0.655(2) 0.1572(11) 0.029(6) Uiso 1 1 d . . . H8A H -0.1168(18) 0.781(2) 0.0702(11) 0.029(6) Uiso 1 1 d . . . H9A H -0.141(2) 0.893(2) 0.1687(13) 0.044(7) Uiso 1 1 d . . . H1B H 0.0661(17) 0.352(2) 0.0849(10) 0.022(5) Uiso 1 1 d . . . H2B H -0.0099(19) 0.187(2) 0.1282(11) 0.038(7) Uiso 1 1 d . . . H3B H -0.155(2) 0.223(3) 0.1653(14) 0.054(8) Uiso 1 1 d . . . H4B H -0.1755(15) 0.428(2) 0.1743(10) 0.019(5) Uiso 1 1 d . . . H5B H 0.0685(19) 0.463(2) 0.1849(11) 0.036(7) Uiso 1 1 d . . . H6B H 0.0283(17) 0.576(2) 0.0883(11) 0.025(6) Uiso 1 1 d . . . H7B H -0.0270(16) 0.680(2) 0.1761(10) 0.022(5) Uiso 1 1 d . . . H8B H -0.0099(18) 0.794(2) 0.0789(11) 0.031(6) Uiso 1 1 d . . . H9B H -0.027(2) 0.915(2) 0.1684(14) 0.046(8) Uiso 1 1 d . . . H5C H -0.0315(16) 0.483(2) 0.2216(10) 0.024(6) Uiso 1 1 d . . . H9C H -0.0936(17) 0.974(2) 0.1166(11) 0.031(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0109(7) 0.0194(7) 0.0153(7) 0.0015(6) 0.0007(5) 0.0002(6) C1 0.0162(9) 0.0242(9) 0.0194(9) -0.0015(7) 0.0033(7) 0.0040(7) C2 0.0270(10) 0.0212(10) 0.0288(10) -0.0021(8) 0.0008(8) 0.0006(8) C3 0.0273(11) 0.0238(11) 0.0434(13) 0.0021(9) 0.0102(9) -0.0056(9) C4 0.0110(8) 0.0266(10) 0.0192(9) 0.0022(7) 0.0020(6) -0.0027(7) C5 0.0210(9) 0.0252(10) 0.0177(8) 0.0030(7) -0.0064(7) -0.0002(8) C6 0.0139(8) 0.0209(9) 0.0173(8) 0.0035(7) 0.0016(6) -0.0027(7) C7 0.0202(9) 0.0218(9) 0.0176(8) 0.0016(7) -0.0001(7) -0.0005(7) C8 0.0267(10) 0.0237(10) 0.0214(9) 0.0024(8) -0.0003(8) -0.0037(8) C9 0.0325(11) 0.0228(10) 0.0273(10) 0.0013(8) 0.0013(9) -0.0009(9) S1A 0.0164(2) 0.0173(2) 0.0141(2) -0.00076(15) -0.00123(15) -0.00119(16) O1A 0.0167(7) 0.0457(9) 0.0248(7) -0.0035(6) -0.0062(5) 0.0033(6) N1A 0.0147(7) 0.0191(7) 0.0139(7) -0.0006(6) -0.0004(5) -0.0036(6) C1A 0.0379(12) 0.0181(9) 0.0235(10) -0.0026(8) 0.0033(9) -0.0047(8) S2A 0.0130(2) 0.0208(2) 0.0137(2) 0.00001(16) -0.00048(15) -0.00105(16) O2A 0.0344(8) 0.0225(7) 0.0162(6) 0.0018(5) 0.0024(5) -0.0047(6) C2A 0.0233(9) 0.0266(10) 0.0259(10) -0.0039(8) 0.0042(8) 0.0063(8) O3A 0.0201(7) 0.0465(9) 0.0172(6) -0.0023(6) -0.0058(5) -0.0033(6) O4A 0.0270(7) 0.0223(7) 0.0229(7) 0.0033(5) 0.0049(5) -0.0030(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 N1 C5 1.497(2) . ? N1 C6 1.506(2) . ? N1 C1 1.513(2) . ? N1 C4 1.514(2) . ? C1 C2 1.510(3) . ? C1 H1A 0.97(2) . ? C1 H1B 0.95(2) . ? C2 C3 1.530(3) . ? C2 H2A 0.96(3) . ? C2 H2B 0.94(3) . ? C3 C4 1.530(3) . ? C3 H3A 1.00(3) . ? C3 H3B 0.90(3) . ? C4 H4A 0.95(2) . ? C4 H4B 0.97(2) . ? C5 H5A 0.92(2) . ? C5 H5B 0.96(3) . ? C5 H5C 0.97(2) . ? C6 C7 1.512(3) . ? C6 H6A 0.96(2) . ? C6 H6B 0.94(2) . ? C7 C8 1.526(3) . ? C7 H7A 0.95(2) . ? C7 H7B 0.93(2) . ? C8 C9 1.516(3) . ? C8 H8A 0.93(2) . ? C8 H8B 0.96(2) . ? C9 H9A 0.96(3) . ? C9 H9B 0.99(3) . ? C9 H9C 0.96(2) . ? S1A O2A 1.4441(13) . ? S1A O1A 1.4485(14) . ? S1A N1A 1.5932(14) . ? S1A C1A 1.761(2) . ? N1A S2A 1.5902(14) . ? C1A H1AA 0.93(3) . ? C1A H1AB 0.95(3) . ? C1A H1AC 0.96(2) . ? S2A O4A 1.4414(14) . ? S2A O3A 1.4442(13) . ? S2A C2A 1.764(2) . ? C2A H2AA 0.94(3) . ? C2A H2AB 0.96(2) . ? C2A H2AC 0.98(2) . ? 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 N1 C6 111.36(14) . . ? C5 N1 C1 110.26(14) . . ? C6 N1 C1 108.52(13) . . ? C5 N1 C4 110.15(14) . . ? C6 N1 C4 112.76(14) . . ? C1 N1 C4 103.50(14) . . ? C2 C1 N1 105.00(14) . . ? C2 C1 H1A 111.6(14) . . ? N1 C1 H1A 105.8(14) . . ? C2 C1 H1B 114.0(13) . . ? N1 C1 H1B 109.2(13) . . ? H1A C1 H1B 110.7(19) . . ? C1 C2 C3 105.65(16) . . ? C1 C2 H2A 108.2(16) . . ? C3 C2 H2A 113.2(16) . . ? C1 C2 H2B 111.3(16) . . ? C3 C2 H2B 110.1(15) . . ? H2A C2 H2B 108(2) . . ? C4 C3 C2 106.39(16) . . ? C4 C3 H3A 108.2(17) . . ? C2 C3 H3A 110.3(17) . . ? C4 C3 H3B 111.7(19) . . ? C2 C3 H3B 111.1(19) . . ? H3A C3 H3B 109(3) . . ? N1 C4 C3 105.34(15) . . ? N1 C4 H4A 105.6(13) . . ? C3 C4 H4A 109.5(13) . . ? N1 C4 H4B 108.3(13) . . ? C3 C4 H4B 114.7(13) . . ? H4A C4 H4B 112.7(18) . . ? N1 C5 H5A 107.5(14) . . ? N1 C5 H5B 106.8(14) . . ? H5A C5 H5B 111(2) . . ? N1 C5 H5C 108.5(13) . . ? H5A C5 H5C 112.0(19) . . ? H5B C5 H5C 111.0(19) . . ? N1 C6 C7 116.14(14) . . ? N1 C6 H6A 106.0(13) . . ? C7 C6 H6A 111.2(14) . . ? N1 C6 H6B 105.3(14) . . ? C7 C6 H6B 110.2(14) . . ? H6A C6 H6B 107.4(19) . . ? C6 C7 C8 108.27(15) . . ? C6 C7 H7A 108.7(14) . . ? C8 C7 H7A 109.4(14) . . ? C6 C7 H7B 110.5(14) . . ? C8 C7 H7B 109.9(14) . . ? H7A C7 H7B 110.1(19) . . ? C9 C8 C7 113.08(16) . . ? C9 C8 H8A 111.3(15) . . ? C7 C8 H8A 109.0(15) . . ? C9 C8 H8B 109.9(15) . . ? C7 C8 H8B 109.0(15) . . ? H8A C8 H8B 104.2(19) . . ? C8 C9 H9A 110.0(16) . . ? C8 C9 H9B 108.1(16) . . ? H9A C9 H9B 110(2) . . ? C8 C9 H9C 113.4(14) . . ? H9A C9 H9C 108(2) . . ? H9B C9 H9C 107(2) . . ? O2A S1A O1A 115.53(9) . . ? O2A S1A N1A 106.48(8) . . ? O1A S1A N1A 113.44(8) . . ? O2A S1A C1A 107.04(9) . . ? O1A S1A C1A 107.13(10) . . ? N1A S1A C1A 106.73(9) . . ? S2A N1A S1A 120.90(9) . . ? S1A C1A H1AA 108.3(16) . . ? S1A C1A H1AB 107.3(16) . . ? H1AA C1A H1AB 111(2) . . ? S1A C1A H1AC 110.0(15) . . ? H1AA C1A H1AC 112(2) . . ? H1AB C1A H1AC 108(2) . . ? O4A S2A O3A 115.75(9) . . ? O4A S2A N1A 113.93(8) . . ? O3A S2A N1A 106.16(8) . . ? O4A S2A C2A 107.04(10) . . ? O3A S2A C2A 106.49(10) . . ? N1A S2A C2A 106.91(9) . . ? S2A C2A H2AA 108.3(15) . . ? S2A C2A H2AB 105.5(15) . . ? H2AA C2A H2AB 115(2) . . ? S2A C2A H2AC 111.0(14) . . ? H2AA C2A H2AC 108(2) . . ? H2AB C2A H2AC 109(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 C5 N1 C1 C2 79.75(18) . . . . ? C6 N1 C1 C2 -158.03(15) . . . . ? C4 N1 C1 C2 -38.03(18) . . . . ? N1 C1 C2 C3 27.9(2) . . . . ? C1 C2 C3 C4 -7.2(2) . . . . ? C5 N1 C4 C3 -84.64(19) . . . . ? C6 N1 C4 C3 150.28(16) . . . . ? C1 N1 C4 C3 33.22(19) . . . . ? C2 C3 C4 N1 -16.2(2) . . . . ? C5 N1 C6 C7 -53.0(2) . . . . ? C1 N1 C6 C7 -174.55(15) . . . . ? C4 N1 C6 C7 71.41(19) . . . . ? N1 C6 C7 C8 -171.37(15) . . . . ? C6 C7 C8 C9 -171.10(17) . . . . ? O2A S1A N1A S2A -170.57(10) . . . . ? O1A S1A N1A S2A -42.39(14) . . . . ? C1A S1A N1A S2A 75.35(13) . . . . ? S1A N1A S2A O4A -38.93(14) . . . . ? S1A N1A S2A O3A -167.50(11) . . . . ? S1A N1A S2A C2A 79.11(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.604 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.062 #============================================================================END